Contents10.1007... · Web viewIndian Institute of Technology, Bombay, Powai, Mumbai- 400076, India 2 Department de Quím i ca Física & Institut de Química Teòrica I Computacional

Supporting Information

Theoretical and computational investigation of meta-phenylene as ferromagnetic coupler in nitronyl nitroxide diradicals

Arun K Pal1 Daniel Reta Mantildeeru2 Iqbal A Latif1 Ibeacuterio de PR Moreira2 Francesc Illas2 Sambhu N Datta1

1Department of Chemistry Indian Institute of Technology Bombay Powai Mumbai- 400076 India2Department de Quiacutemica Fiacutesica amp Institut de Quiacutemica Teograverica I Computacional (IQTCUB) Universitat de Barcelona C Martiacute i Franqueacutes 108028 Barcelona Spain

Email sndattachemiitbacin

Contents

1 Log files of optimization ROHF6-311G(dp) Page 2-32

2 Tables of computed total energies and ltS2gt values with B3LYP B3LYP-D3 and M062X6-311+G(dp) scheme Page33-36

3 Reference 43 in full Page 37

4 Reference 44 in full Page 37

5 Fig S1 Calculated J (B3LYP) versus χp the factor of planarity (a) Common ortho J (cmndash1) = ndash270+2061χp (RMSD = 10742) (b) Ortho-para J (cmndash1) = ndash008+2324χp (RMSD = 106) (c) Common-meta J (cmndash1) = ndash1245+4544χp (RMSD = 065) Page 38

6 Fig S2 Plot of calculated J (B3LYP) for Type (c) species (common-meta substitution) versus σm J (cmndash1) = 4068σm + 2122 (RMSD = 0322) Page 38

1 Log files of optimization ROHF6-311G(dp)

Unsubstituted NN-diradical

11GINC-COMPUTE-0-38FOptROHF6-311G(dp)C20H28N4O4(3)SNDUTTA11-J un-20120p opt rohf6-311g(dp) geom=connectivity scf=(conver=5max cycle=800)Title Card Required03C-0000161984132623123453-00 011372355C1200554823725795727757-00178425666C1205035769118 56591565-00341576317C0000078532404940457273-00006931255C-1 20507820151185415151200327489987C-1200772492225793461682001 59616154H-000028381443366517088-00013480395H21319414622310 64440068-00045799037H-213223892053106055526200027352899C-2 4833421628045847996910062292401C-39626027378-13824978295019 66348048C-47288117546-00578980121-00993789576C248342795304 589369507-00628936493C39630109972-13816737352-01976422928C4 7286374968-0057450548201016897907N360172229170877427902603 830134657N26679429011-08169543384-0616366726N-26669056886-0 818304770606140667197N-3602438595408774758828-03812053841O -17840200162-1487357786311783978615O-3861590244120003558439 -09320139976O38597424651999544382509359108512O17854466104- 14856311577-11817934267C-546753884850528248458911102434226H -577161730981537376526708662716152H-63500657426-00571252106 13425205996H-483414560720566770247719892973034C-5664650412 9-01010136925-13023185635H-64420074609-08399168226-11313103 269H-6123522886908677586913-14322829616H-51438606682-03451 857415-22175942991C-45529701902-2245012965913076701309H-55 447628777-2582586299110242049678H-39296009173-3116600421146 04056111H-46209977971-1713910817222468234594C-37100312262-2 2464083578-10474095419H-30219842716-30416873289-07850093605 H-462989089-26948458662-14044381267H-32701656609-1672637924 8-18548962888C56624039034-010232378613061748852H6440337530 5-0840636356311352372496H612067421820866397700414386198245 H51401200447-0348282165822201178122C54694253305305703249-1 1057662423H5772948087115393736906-08597727826H63524335389- 00543521543-13373538308H483757845830570308995-19858800186C 37084530356-224749806410446673234H30209336719-304244837250 7799112962H46277700981-2696374787714025425495H3267185324-1 67500609041852296257C45552854176-22424599989-13089999038H5 5464915648-25806952803-10242721328H39320283662-31136804708-1 4643002644H46251352912-17098271446-22471523155H00002331966 -05719838356-00005122093Version=EM64L-G09RevA02State=3-AHF=-12 909079153RMSD=1412e-06RMSF=7911e-06Dipole=00004947-21403457- 00012474Quadrupole=177749836-8318343-9456640500146328-89733 296-00156422PG=C01 [X(C20H28N4O4)]

Job cpu time 0 days 0 hours 1 minutes 22 seconds File lengths (MBytes) RWF= 325 Int= 0 D2E= 0 Chk= 35 Scr= 1 Normal termination of Gaussian 09 at Mon Jun 11 130108 2012

1) Molecule a1

11GINC-COMPUTE-0-73FOptROHF6-311G(dp)C21H28N4O6(3)SNDUTTA07-F eb-20120 opt ROHF6-311g(dp) geom=connectivity scf=(conver=5maxc ycle=800)Optimization Triplet of the molecule03C-00084354773 1695404602-00268926151C118767680612487756291400440054417C1 20673837711100153045800331108953C0010382626203833055213-000 2820918C-1198905030210795479829-00565294379C-1193858567124 68809451-00889972807H-001749236854243582031-00344441216H21 1571279683018468266901197586362H-2127480908829873700083-017 46291563C00751113755-1112723346600423085982O08473934697-17 18153333606986570622O-08079271908-16955982888-07497977554H- 07035791829-26320951417-06649301733C-2536682900304489036945 -0015001769C-42881762773-100674689260613680934C-48063170344 01611599195-0285876898C25436447991046893562670002227267C4 2881979719-09970473126-06116502418C47990591469014432064830 3281666255N352012974590790657892707459845386N2968969125-04 412367627-09688557004N-29500602497-0481377758909428100682N- 3528321803807907183914-07318560859O-21764961024-10326346945 17450879518O-3560476733516635534214-16602328972O35355201965 1651819634116863978199O22132017372-09480936835-18155005862 C-556190701071256068214204776821722H-569776240782101470127 -01829261676H-653505777690899066492507948311781H-5013627543 9159039319471351267982C-5613928191-02602762004-15088165754 H-65169857398-07728591188-11912631784H-58890552775061939404 87-20716230988H-50535333638-09110316677-21653519999C-50851 264365-1254023867918916978193H-60947420878-1567054839316454 899097H-4614788715-2045912970424608677819H-51356373374-037 6000872825202005309C-41057728928-23320041636-01386061749H-3 5845399619-3029380649805070439453H-50660993401-27624948263- 03976686928H-35256633642-22046711696-10433409604C5554164334 1-0318875116415694145218H6459113863-0840721127412729801136 H582360019210543006889121620370952H49577618898-09744470998 21881608931C5601883251512390368988-03855408978H57328940108 2067063609302977537169H6577502733408686043771-06789759101H 5089669046816038210319-12689166595C40592080222-233490513680 1042202666H35569714057-30116095837-05767195817H50045179982 -2780088781703936001854H34341271546-222392935520979454178C 51195339469-12274023639-18707215767H61152761628-1564896525- 16012723542H46533481908-19975740898-24720747583H52055798972 -0336270429-24768479052Version=EM64L-G09RevA02State=3-AHF=-14 78561686RMSD=6732e-06RMSF=4272e-05Dipole=-05358007-12551541- 02984989Quadrupole=247219366-17450741-22976862524724798-145 2034282074405PG=C01 [X(C21H28N4O6)]

Job cpu time 2 days 5 hours 21 minutes 35 seconds File lengths (MBytes) RWF= 418 Int= 0 D2E= 0 Chk= 40 Scr= 1 Normal termination of Gaussian 09 at Tue Feb 7 200614 20122) Molecule b1

11GINC-COMPUTE-0-25FOptROHF6-311G(dp)C21H28N4O6(3)SNDUTTA25-J an-20120 opt ROHF6-311g(dp) geom=connectivity scf=(conver=5maxc ycle=800)Optimization of the triplet state of the molecule03C-1 3718134679-0252855232-07659217195C-14168630625-01902283960 6150444281C-0222248193-008522618413309030652C09835635576-0 065583425706485527425C10225904612-01517339951-07387171952C- 01696319516-02499310152-14465701864H-22945389224-03184932895 -13086873905H-01484569723-03402515726-25121278316C23088319 283-01547732208-14535961711C39736514561-06446798041-2974388 6313C4510947015504759450483-20368242615C-01729629554011604 719827886961813C-04692169911038534512548734868128C04034288 384-0245589416950425697065N07799793211-04740822512363179054 04N-089754243080916824332434516969297N25322061717-06797828 094-2592574941N3505443567203955414374-09569432095O17161808 442-13072392054-3341756039O35491321695116676418150023431379 9O14823619847-1446466885732839387976O-18390078667165258772 3930076966091C4424731797418824570376-2646695425H4648339486 626123255853-18784531936H5143220692320001005401-34491514286 H3435564646120945205765-30361112354C591075042830246265668 -14753025609H663793604102352230238-22809982456H61656325725 10552752603-08021070255H59841299732-06826923522-09272104451 C40990981484-03648007761-44680479442H51474745424-0259917855 -47309278565H36800906993-11917503727-50218837339H357277024 9605322047193-47629308401C45184777674-20447029029-266330084 16H39242879694-27692111149-32038287757H55515796396-2131537 2818-29802356868H44575676175-22757226224-16059730249C16506 291344-0080487869159053523215H13689398112015085532566927768 1244H22086600313-1008653516859112810369H230189980080700574 996655384602024C-03916204031-1472352587755115684152H024349 98407-234727703854443011932H-07074577141-135858173686541985 6718H-12656920231-1642025424148942648917C03160440344235337 8127549589087143H-032205452313154083477246094350985H060933 270852559010525359822071202H1204852521823328993894338712184 2C-169997312311116011597857702251508H-13927551311113615119 1868115420769H-22446058112021783863355475270685H-236883982 080280379945356192590732C-27822622227-028785143711227610139 1O-375811122070121552384907067820108O-28080317919-09862101 3423545984506H-36901355884-0945553534826933839325H18914001 3670027152782112027459557Version=EM64L-G09RevA02State=3-AHF=- 14785710802RMSD=6206e-06RMSF=2719e-05Dipole=24988137-0127853 13140929Quadrupole=-32793627-11936097215215459986546426-180 616805-57584788PG=C01 [X(C21H28N4O6)]

Job cpu time 3 days 17 hours 34 minutes 510 seconds File lengths (MBytes) RWF= 419 Int= 0 D2E= 0 Chk= 41 Scr= 1 Normal termination of Gaussian 09 at Wed Jan 25 105338 2012

3) Molecule c1

11GINC-COMPUTE-0-100FOptROHF6-311G(dp)C21H28N4O6(3)SNDUTTA07- Feb-20120 opt ROHF6-311g(dp) geom=connectivity scf=(conver=5max cycle=800)Optimization of the Triplet Molecule03C000510316852 76813375400259390846C-120215497242087752626400560515345C-1 21131414660697953705400602009187C-000835400680003093956200 051419407C1200476064206860711683-00420738737C1205146302820 783906965-00172623324H2135847744426043853671-00153484555C2 4739641875-00470319738-00962182326C47184857516-057290512990 0320820328C39439608605-18901525228-02783091947C-24905578094 -002560803701024769119C-39775036777-1853322462802914136779C -47355273736-05359599587-00587953083N-360188232250384095426 1-03654745145N-26802989523-1281588840606963301127N35981007 5190361626409403422500558N26444507101-13150041364-067037958 16O38625256134147437897109073203636O17461233213-1974279843 3-12216851646O-3843716463214862298014-09565101971O-1791679 6166-1940963893312629491228C3703701962-27753066317095306692 8H30108897431-3564408954106848423926H46266995832-323190222 7212908961071H32750884091-221514468951776052045C4517732608 7-27341447648-14120291721H55113425235-30808002975-114668990 94H38889985194-36003645969-15731919154H45768393036-2186014 9661-23419302848C56669928567-0639111684812239355124H644111 53928-1375900126810310953171H612907696310326438078513660713 193H51559089327-0899016834621403243402C5445347749800322132 191-11753819981H575673527710355377266-09172226097H63224754 205-05526512333-14281112433H480217972200890069612-204628419 47C-56618321228-06169920372-12670461281H-64462938202-13429 671668-10749270311H-6112018864103498036522-14363540644H-51 359414444-08990418182-216841377C-54796405675009846047681122 8352791H-577728405981099231226708397860136H-63663588429-04 7428839113698568956H-485254840970166833922420045351423C-37 224211466-27640618152-09181267502H-30419358932-35538969214-0 6220189315H-46431559181-32188490241-12644447009H-3273649461 1-22234611826-17434750028C-45789281618-26705411068143040513 21H-55698524184-3015662911611532444607H-39594698462-353761 5010716205970001H-46516194136-2103445100523478743151C-0035 27908054256565720100526719326O-1023137534248960405290174880 7334O1161503748248135695816-00742260727H105565734555752014 1617-00331447093H-21216981092635147902200640167589H-001454 90818-10634927477-00014220377Version=EM64L-G09RevA02State=3-A HF=-14785795825RMSD=1848e-06RMSF=1623e-05Dipole=05369905-2671 3338-00506323Quadrupole=174494875-77271946-9722292967704423 -92865114-04491058PG=C01 [X(C21H28N4O6)]

Job cpu time 1 days 7 hours 39 minutes 463 seconds File lengths (MBytes) RWF= 418 Int= 0 D2E= 0 Chk= 40 Scr= 1 Normal termination of Gaussian 09 at Tue Feb 7 171728 2012

4) Molecule a2

11GINC-DAVIDSONFOptROHF6-311G(dp)C20H27F1N4O4(3)SNDATTA26-Mar -20120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCY CLE=900)Title Card Required03C-1244457931911240438439-0180 8879621C-124945572442506678049-03035191355C-00652160832104 751278-03967827039C1139195435325359780625-03464581825C1171 95665221157711466-01735258186C-002820067530470460765-010987 2358H-2189027036730250286361-03393888134H20664830929306296 34044-04514417254H-0079474906942771027501-05176485336C2461 375151804586365966-00799188724C45872910773-02740653018-0545 0375393C4206315752-0802669924708730230816C-250278861360367 1610896-01397732958C-42276721937-10551892621-06693082053C-4 5174515194-0460461018307452977785N-35567986472066092742730 7384596527N-28289741493-05880288964-09090079427N34757801889 06857585076-08087479284N27501255922-0549949040208498936765O -343543211111447458559816993643513O20407950339-07329717013 18644484959C44832046679-2283153838411159552586H55501794022 -24779060510698838333H41330733219-2555519671621042421874H3 9812283701-2914831691503966533854C480744139590028059097420 157428913H43665449608-0290731533729520163046H58796213868-0 116345159520762145955H460930797151086944205418928215527C44 942448006-13271707785-16568704615H45461884514-08201946291-2 6112679593H5317027074-20298515115-15876724171H35607880432-1 8762337525-16145690858C592350132340454234729-06368915784H6 7278520706-02261215474-03734389665H6072150288607969427841-1 6501997133H596725585121316470723300137982287C-41265995228- 1397317041918972693632H-41919032811-085040106928300932434H -47979468033-2246310067119510184009H-31123332852-17646992562 17915604079C-59370236070054231149609607395009H-66451171388 -0766002054108978612815H-601414584620491732114219484067514 H-621318791780808624585402371292132C-4273900452-25763144495 -0762725229H-52724292477-29266615189-05186015763H-40330845 198-28772724349-17716648242H-35636748753-30483986305-009840 18307C-50669329478-0440175785-17957503987H-4639620953-0741 8746738-27426164381H-60913743013-07911132064-1744637564H-5 067719773706431777834-17530111921F-00148382958-083373076750 0238412462O3581797837715254794038-17613621415O-21650368303- 10715678956-18724668267Version=IA32L-G03RevC02State=3-AHF=-138 97745907RMSD=2955e-06RMSF=8006e-05Dipole=-04759549-049613881 2916806PG=C01 [X(C20H27F1N4O4)]

Job cpu time 1 days 18 hours 45 minutes 24 seconds File lengths (MBytes) RWF= 370 Int= 0 D2E= 0 Chk= 39 Scr= 1 Normal termination of Gaussian 03 at Wed Mar 26 173142 2012

5) Molecule b2

11GINC-COMPUTE-0-79FOptROHF6-311G(dp)C20H27F1N4O4(3)SNDATTA17 -Jan-20120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5M AXCYCLE=900)Title Card Required03C-13165319518100331013340 0763974658C-133557586192393297067201985344972C-015908963843 107455284302690506568C104180637912434387630202206532696C1 0975851181060339051900806738434C-00904250774034974029030012 5510236H-22653686472919766526502491745998H-015751234494175 869794303699305877C2384264837903598769771-00221504494C4417 2871416-0381820403-07894016034C41783729571-1018347646206172 505487C-2560139169402253700482-00100976286C-41116239546-13 835260507-05872005918C-47678770716-0463520746504833349707N- 381421327780664796301904537938832N-26941389515-0927876472-0 5344891715N3301936914306087103143-08621319712N27353143124- 0743863618207675174644O-396263473021654967013611988368777O 20934364581-107316666617856824368C44479657904-251676435570 7125381978H54990748201-2719634484905326971234H42030226839-2 862730499517091852415H385736611-3083541188400064346952C49 092690117-0288446441417533625052H4556960842-067555762182701 7928965H59789526206-0451485974416938989346H472111841410778 887990517328388974C41905039049-13432584738-19626377015H415 70024966-07644787819-28758079281H50004950056-20607077217-20 305372176H32544127841-18814269343-18676926817C574752632303 421129784-09646857311H65653076069-03621792354-08439176902H5 792352490907650904503-1957476468H5871109798711488280988-02 557566739C-47433811338-1053033710819009011306H-5051005047-0 288791204426040510994H-54281571022-188866569719836160312H- 37521637669-1390668351421810330769C-61758321351002425128960 156073687H-68597937178-0817264097101103949413H-65160254160 693294648109366473163H-6216141883105565785779-07840613865C -41785879938-28785686052-02942925875H-52166320353-3194992979 6-02527525333H-36789680964-34186681593-10847399276H-369626 72542-3135402777406384284444C-45814661038-11177657402-20232 638627H-39128846116-16319455994-27005621797H-55882232656-1 4914499197-21723317426H-45627150978-00611102342-22646908261O 3302554435914886376346-17737020678O-17998316828-16424170737 -11021812134H-00701490923-07124011726-0107993619F215333718 2431208580150348969716Version=AM64L-G03RevC02State=3-AHF=-138 97806474RMSD=2905e-06RMSF=5925e-05Dipole=-10374304-108869570 8374704PG=C01 [X(C20H27F1N4O4)]

Job cpu time 1 days 18 hours 17 minutes 454 seconds File lengths (MBytes) RWF= 375 Int= 0 D2E= 0 Chk= 41 Scr= 1 Normal termination of Gaussian 03 at Tue Jan 17 071847 2012

6) Molecule c2

(Enter shareappsg03l9999exe) 11GINC-COMPUTE-0-74FOptROHF6-311G(dp)C20H27F1N4O4(3)SNDATTA21 -Jan-20120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5M AXCYCLE=900)Title Card Required03C-119123001409826078519-0 1789324241C-1170274937523565733178-04008405778C004443112252 9844642766-05198869284C124118024123179350571-04221154083C1 214198273309490075983-0174832402C0001852249802787583837-00 649600687H-2066991262529347466506-04810021146C248100264802 08141058-00688492272C4631750258-05241353251-04539303528C40 854886362-1301496193507805741499C-2469620086502609402963-00 847695872C-41067132948-13466762052-03206290935C-4687943028- 0213646697605753372882N-368713287860841869784803150254291N -26676479814-09604885891-03856892657N3579202327805165041652 -06334722523N26476453871-0984505465706559264203O-3761184248 31955973663308734776663O18239289199-1382573909115067677C4 2987221217-2811983577207511517583H53598977325-303946151250 7730732253H38400023038-3256956430316254558704H38618106533-3 2689228875-01256813188C45709856588-073910579662124283798H4 0180875183-1215534616329244328449H56253622052-094194680122 69916204H441317284020331109098521952654314C46392924402-133 34175153-17572242091H48118648259-06521904309-2579688945H54 310486163-20739108533-17426558868H36940451396-18365883437-1 9249652185C5986584833101477309984-02589359688H67398096606-0 6063908626-00509992797H6256547125806727501898-11632100001H 597654105520864894381705499251327C-46449617773-053300013142 0766666779H-489884269850361032231226327714499H-53613211402 -1306249505423276869541H-36607283993-0859352190523926120824 C-608295777270273004044301952194879H-68042231006-0528155159 403217512601H-636882677551090045722208458841345H-612929191 5206248999362-08259781282C-42310887143-27573088702448517375 H-52804754811-300835615380367632561H-37814262944-345768146 29-04432396769H-37317237806-2862280932111978125099C-460742 89298-1325300441-1770597057H-3984933164-19890197499-2355467 1875H-56345389487-16679051112-18254939778H-45475877547-033 32954677-22035618717O3816530009715080448728-14002232998O-1 8262031501-18065700862-08319473675H-00306207306-07761508300 880575409H2166865997328375674549-0557024816F00597573302429 24550295-07455475832Version=AM64L-G03RevC02State=3-AHF=-138978 39012RMSD=2490e-06RMSF=6936e-05Dipole=-07379091-157052510091 602PG=C01 [X(C20H27F1N4O4)]

Job cpu time 1 days 3 hours 52 minutes 518 seconds File lengths (MBytes) RWF= 375 Int= 0 D2E= 0 Chk= 41 Scr= 1 Normal termination of Gaussian 03 at Sat Jan 21 192054 2012

7) Molecule a3

11GINC-PAULINGFOptROHF6-311G(dp)C20H27Cl1N4O4(3)SND26-Apr-201 20P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE= 900)Title Card Required03C-12045608554-1182254805900016105 018C-11921602255-2567446737100016384971C00000108302-326281 28059-00074474167C11918825533-25668964894-00151920117C1203 6907293-11817193378-00129765995C-00005860946-04956559041-00 056124768C25053965108-04824749865-00152669215C449850068790 4205326903-07032675033C435307678060701141818508295306673C-2 5065542396-0483596969600109201616C-44978950530415204244407 077864817C-4353316215207076998948-08227163723N-32517899025- 02214877891-11431348961N-3141367798-0115777974410426625207N 31443107881-01127097763-10436994481N32466479496-02249315643 11422509029O-27809111334-03468243822-2292455683O2771646756 4-0353644141922894858247C55789628845036761330416747188426H 641057545481007335117713964789005H53521619464054399510872 7188702524H58824455944-0664600655915679202075C387842805392 124353538611540429411H364465943482181874529422102443651H46 5329477482849869857409349496129H298783059222389066734805979 005498C54813498813-07047840355-10486961297H53734439616-094 13720706-20986565306H65023002381-03921382341-08615616732H5 2834986842-16032073505-04748551342C4790421210516412391772-1 5688688253H5745588501720715505592-1283075644H4837092808213 380687402-26044847639H4023951670123982587647-14799699527C-3 87152074352130909968-11364391487H-3628665070821926204592-2 1903615389H-4645994425628577914374-09204710616H-29848276739 23902509672-05716229638C-5581964976603872959942-16689782832 H-641185306610244506982-13799304076H-5357726169305774228524 -27112754096H-58867094754-06458204897-15753429955C-4793903 35731627937766615831051718H-5750363675620574850858130049832 5H-484000242071316191557126162110472H-40297987623880721021 1500712569C-54757330371-0716910219710450091468H-5342159905 3-0984102507120846592209H-64999756621-039602649770892979914 7H-52956274038-1598873871704406356785O28025362309-02374991 751-22588904385O-27949437176-0242562088122563226017H212637 64932-30966796232-00266679056H-21264133524-3097640724900142 290699H00002570691-43366516806-00075913239Cl-0000926144812 391259136-00029458083Version=IA64L-G03RevC02State=3-AHF=-17498 072035RMSD=3070e-06RMSF=1149e-04Dipole=000127950238615500050 333PG=C01 [X(C20H27Cl1N4O4)]

Job cpu time 0 days 8 hours 6 minutes 460 seconds File lengths (MBytes) RWF= 382 Int= 0 D2E= 0 Chk= 41 Scr= 1 Normal termination of Gaussian 03 at Thu Apr 26 020948 2012

8) Molecule b3

11GINC-PAULINGFOptROHF6-311G(dp)C20H27Cl1N4O4(3)SND26-Apr-201 20P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE= 900)Title Card Required03C-13584251489-09535127937-0243547 9113C-13655120393-2330212634-04508447292C-01810341704-3034 4053749-04975768757C10217262132-23724111708-03400215789C10 514266328-10047173948-011677947C-01431201381-03029263221-00 767942839C2299533774-0246710071800830409551C40140028537125 10973908-01993807835C41130093610684055182912537306952C-260 71828955-0180635133-01855130899C-42029571384137458725970410 3966691C-4756384855405757824748-08069268263N-38120015906-0 5606959349-08026471795N-278666569120910519628504460806243N2 683365990207281177646-06308040534N32031662167-047229849131 127635851O-38881662218-14724098044-16513787935O2934521643-1 220386863420910135495C550264266170223369046916825754509H6 18435131711067658305317124396228H54478768561-02013669295267 74178218H59066406464-0528434182910190833742C35277947941621 529043423195543987H347394437861089648911832615477926H41558 9076352494203295524551708035H252789048631952374987206295915 78C5029392421106536857836-11813061612H47351601250930158782 6-2185121441H602302510591041699518-09874168164H50583093557 -04280687693-11212633967C4021204871727715448492-03109669711 H49607995269315991995500707060829H392146536130519086995-1 3492516032H32062827437322641936602344601632C-459502005741 3061737074-21478541633H-4838326657906216678505-29511774136H -5265205539521554875923-22081103459H-3580260676316560510591 -22984866036C-6190252735900745289276-06654999616H-687329897 3409152512862-05972934686H-64566217661-05061036304-15398711 166H-63209958694-0551485766702062448221C-42382662712289234 9491502667005997H-5266902460832235057701593316307H-3815460 18783343673877511520478127H-3668358023132364069487-05849559 016C-48072569443096904791551760827347H-4206439864140577376 825472305518H-582358284591335552383918507164472H-481188791 46-0106791459718941678368O2124680679312018269217-1670134595 1O-194942833121547831431111667620408H-2287840954-285557173 6-05881259822H-01855068544-40933504944-06672786203H-012678 274540753021486600878678789Cl24897641709-32892309525-047693 3721Version=IA64L-G03RevC02State=3-AHF=-17498212259RMSD=5739e- 06RMSF=5128e-05Dipole=-085693930517108504182686PG=C01 [X(C20H 27Cl1N4O4)]

9) Molecule c3

11GINC-COMPUTE-0-21FOptROHF6-311G(dp)C20H27Cl1N4O4(3)SNDUTTA1 0-Apr-20120opt ROHF6-311g(dp) geom=connectivity scf=(conver=5ma xcycle=800)Optimization03C0000031705730723554832-000125931 31C-120495344732403930179900142094464C-1203568616810111492 26900320625787C0000006546703183342863-0000083244C120359874 7610111174854-00328209652C1205016316824039068106-0016160898 6H2130651623929390524646-000075997C2484139824802868587082 -00633338216C47319689678-022021669310093338131C39676796614 -15506005031-01824292509C-248416361490286976768100632120318 C-39679949578-1550114367601845307309C-47320518877-021998460 09-00930504287N-3603226461207156840224-03701381964N-266822 75857-0994568423806027982391N360329276070715947928203694118 175N26679836508-09953784494-0601314751O3858344313218443331 48409045927068O17835071463-16730171384-11524922055O-385811 8832818435230708-09065555654O-17835482139-16720469591153869 1752C37231656864-2399427635210734822691H30364143837-320000 099840824263312H46460186222-284058225241431636152H32855322 694-1817064218418760665727C45552884426-24248715436-12856421 666H55492745879-27560842367-10025888502H39337724401-330005 88669-14245545952H46174408778-19051689974-22315259916C5673 6066752-0244888654312921611187H64527984686-0982741186511257 225778H612971037620726986921314080368254H51586161543-04803 33777722129659403C5461509256303542967204-11273831395H57652 39982213667649207-08973010076H63437595758-02320179094-13577 940433H4822986735703810550532-20031230511C-56735117086-024 60583248-12919845403H-64528817084-09835306405-11246960178H- 6129396850107257573307-14092142443H-51584238378-04828285263 -22123958591C-54617055935035617516511268276627H-57652628688 1368389728708954116731H-63440697642-0229730695113578423323 H-482331624340383958064820026328222C-37235494266-2400645511 1-1070241469H-30370693657-32010942241-08198867427H-4646483 8985-2841995972-14279420996H-32856399199-18194554224-187352 5312C-45558372092-2422823595212888584555H-5549831481-27543 11091410061540546H-39344331857-3297893450714290220113H-461 80326752-1901826539122340288647H-2130576084829390765143-000 16751177H0000000839-0747201411400003673277Cl00000330906481 60511545-00020246815Version=EM64L-G09RevA02State=3-AHF=-174982 71418RMSD=4142e-06RMSF=2396e-05Dipole=-00001567-301750680001 9522Quadrupole=223935184-14282327-81111914-00063575-8507781 00031926PG=C01 [X(C20H27Cl1N4O4)]

Job cpu time 0 days 6 hours 33 minutes 173 seconds File lengths (MBytes) RWF= 381 Int= 0 D2E= 0 Chk= 37 Scr= 1 Normal termination of Gaussian 09 at Tue Apr 10 231206 2012

10) Molecule a4

11GINC-PAULINGFOptROHF6-311G(dp)C20H27N5O6(3)SND01-Feb-20120 P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=900 )Title Card Required03C1212694047811408206992-01551686789 C1169069087525119313545-03581206544C-0036895101731814085973 -03926033358C-1216650812524847377156-02402766797C-12075263 74211064191694-00686812207C0015214118804515245303-001593458 46H2088998860230519695537-04717050697H-2157990442929965087 281-02372346142H-0056683285842462202115-05307050533C-25174 611025043030850400052726453C-46564604468-012403197340621287 5615C-43396098538-08802315158-07093444311C2535034440305058 9146-00216803186C43502261689-0583841227908655678458C465584 0721-02875764067-06402550671N359111429207014324824-09185937 546N290927273-0208563444709525850844N-34975794088081649076 5307113037366N-28797280451-06771885871-0763773964O34390800 23912334681217-20369736939O-21635774602-1116169396-16828272 306C-4665599777-23707762438-07067540761H-57344368944-25189 523202-05886027895H-43664053751-28047548328-16527965186H-4 1481571246-2898048222200819889766C-49457987005-02192104577-1 9550465081H-45373080676-06962651731-28375243556H-6023022145 7-03357611594-1970644898H-4713185568708386568907-2005328129 C-45689448257-0997634686618792026457H-45845921594-03493774 81627454059583H-54149001306-167365231519324236363H-3652846 8817-1575070762519043386246C-595772235606693122997062926438 2H-67959249004-000808406580496889866H-60611004073117282567 3315790969395H-5988277476214192604736-01489895115C44184493 614-14905190343-15640358114H44902057794-11586920533-2592905 6075H51678389752-22560147929-13998970183H3437151624-192395 89701-14159586579C6027554022103171210739-09213799244H68072 211868-038988512-06564736222H6114187859205334841918-1978951 8919H6191424212212361576645-03757315804C4513060059-2039278 540512908934926H55459428523-2345371405911542902488H4254127 3354-2134703632323352941878H38700289161-2701311993507288549 635C507937982520333342463918544110195H46382204380199066717 728331369367H613195030490079403197419064202623H49867691401 1378297503915804572165O-35420983434180140565515141216145O 22160190414-054528338751960555743N00384206853-100304494740 1858642197O07900770499-16297309586-04814604544O-07148569874 -144670716860980764576Version=IA64L-G03RevC02State=3-AHF=-1494 4078162RMSD=5517e-06RMSF=4384e-05Dipole=0384125103978729-12 171651PG=C01 [X(C20H27N5O6)]

Job cpu time 0 days 2 hours 16 minutes 139 seconds File lengths (MBytes) RWF= 379 Int= 0 D2E= 0 Chk= 44 Scr= 1 Normal termination of Gaussian 03 at Wed Feb 1 162303 2012

11) Molecule b4

11GINC-GINSBERGFOptROHF6-311G(dp)C20H27N5O6(3)SNDATTA05-Feb-2 0120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCL E=900)Title Card Required03C1446224871308330138746-0166587 3914C1446417750321987824909-04195946994C025121078822874064 9193-0576584599C-0935046068121831311714-04994449367C-09684 63212508218703393-02292105016C0233193743601570572467-005943 15546H2365353719127393794936-05048419403H02373869959392788 06956-0768769817C-2214503801400735437556-00042571221C-4196 1276072-060930905260927463238C-39174684485-15079208262-0322 8757223C270641766480095827968100208360591C42869038402-1386 606395408127038769C49276566442-06053702093-03722662066N395 2069058304986719621-04940846936N28571993339-097298581340696 892408N-313995434070432708773507797877512N-24913921053-118 39224356-05481129883O407512668091377802832-13717252764O-18 305797607-16714901413-14884101569C-40916789673-30067998593-0 1012492535H-51285060458-3231269048101283805969H-38248953185 -35366285387-10073876836H-34685086306-337789619050700509057 C-46915580544-1072576576-15750746975H-43208362418-16315706 453-24258844459H-57495329723-12805629594-14657159486H-4562 3770434-00169923802-17806688796C-39204184561-12921818305227 25401668H-39226713458-0535216392930456665257H-46902500376-2 02240592652494985866H-29559575174-178689122042284610127C-5 5640517509006369017409567035479H-63422922597-0693271993109 816405532H-564009757750673846925318449342583H-572077803890 704672607201008821326C49178867051-13808527761-16974210206H5 2160309729-07135519256-2496593708H56165178556-22083334897-1 6652703351H39336458614-17700230971-19318309587C63250232418 -0051090241-01127272721H70250173791-086540797090044664882H 66539634062051393798-09759030657H6352755390906029243252074 765545C43861295687-2905648331407256052812H54309611886-3201 028442507288131383H38957351799-3344905783215816299172H3914 2118401-3297247172-01645837116C47418786295-0916422153220029 44325H40852877208-135260035352941092902H57573653885-123994 4705623979605379H469511232370162244135422968623869O-318858 66351503682107514618145576O19772226687-16198507021134828217 83H02348816521-08843765040179790809N-215675550422937698055 4-07983512199O-219261324284068265945-04584790811O-29972511 39623769427901-14217418712Version=IA32L-G03RevC02State=3-AHF= -14944179734RMSD=6946e-06RMSF=9113e-05Dipole=2136464-20279081 -02034122PG=C01 [X(C20H27N5O6)]

Job cpu time 1 days 15 hours 2 minutes 175 seconds File lengths (MBytes) RWF= 384 Int= 0 D2E= 0 Chk= 42 Scr= 1 Normal termination of Gaussian 03 at Sun Feb 5 064748 2012

12) Molecule c4

11GINC-GINSBERGFOptROHF6-311G(dp)C20H27N5O6(3)SNDATTA09-Feb-2 0120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCL E=900)Title Card Required03C1206937476706707635481-0086418 4981C119985147220492890526-02491255003C-001406761322701345 1323-02953026193C-1221494127920454974028-0189658169C-12081 26223906625240432-00472828728C00012940998-00185167673001513 56782H2103265257726120553067-03374880885C-24776143682-0068 207144500763938023C-46183381199-0649385170406957996238C-41 057385546-17338715228-03002584488C24756168272-0066607936900 059227224C4095014863-1572025744606563382672C46773732117-07 343213427-05218801709N369021235550366144037-05519829318N26 61239096-116065259690628157115N-355685611550390850023905674 931803N-26629708447-14087265425-02997505267O37574340219127 73854336-14040348656O-18599640952-20186144369-10379623828C- 43222972826-3179429881701366664496H-53841913214-33925125659 02080812947H-38934941866-38459692207-06014269802H-385883374 84-3391806054110898552601C-46237536519-15447271346-17330694 606H-40933814475-22222380316-23906887829H-56820199743-1769 0175351-17933831908H-44655540409-05335477178-20905612223C-4 5962144465-1082026887721675053614H-47435409236-02045762922 7828342341H-53925915849-1789403398223689659935H-36501633215 -1534759616224411814567C-59741787576-0038173056803594667387 H-67358531273-0811873690303757282802H-621972835970710572044 310980299278H-5980214948204390146449-06105297572C461277000 79-14518687762-18776381281H48629980664-07463945378-26602922 82H53226596334-2269500731-19155100869H3623244167-184525063 93-20808826211C6081614444-01804609248-03012031839H67916206 633-09949966194-01993022905H6372329357304149171917-11577817 382H614093598250445335261305783021706C41944456426-30851222 36804956654961H52387290156-3376069128504340891623H37476246 265-35644490613541281397H36797045218-34385242342-0386787072 2C46155300963-116334107382040287631H39916442797-1630125161 27906484321H56378625472-149678117621771171972H45772273381 -0089819022121855658298O-37623239611552809232210469888146O 18103766628-1834318972312971936308H00248556663-107606815690 1582715326H-2142322566725880934855-01983954399N-00160716414 41570563801-0457842854O-1061969727846885198476-06226904658 O103226816347133431557-04177891749Version=IA32L-G03RevC02Sta te=3-AHF=-14944281936RMSD=1343e-06RMSF=3989e-05Dipole=06741362 -30902857-03893361PG=C01 [X(C20H27N5O6)]

Job cpu time 0 days 19 hours 7 minutes 530 seconds File lengths (MBytes) RWF= 384 Int= 0 D2E= 0 Chk= 42 Scr= 1 Normal termination of Gaussian 03 at Thu Feb 9 071422 2012

13) (a) Molecule a5 (6-311G(dP) basis set)

11GINC-DAVIDSONFOptROHF6-311G(dp)C20H27Br1N4O4(3)SNDATTA24-Ap r-20120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXC YCLE=900)Title Card Required03C-1200765233912060336429-006 26905118C-116784014042591582368-00055202218C00320148173327 0876998500163535728C121309204822559042738100091622437C1207 139646711715780362-00010164698C-0006794828604955774837-0057 3501706H-2094861780231343957251000463852H21559223717307096 59464-00000641644H004722795244344475514500329327964C251687 919220491129705900412698845C46312141193-02090934588-0514125 6768C43911740676-0575629060509857251675C-25252284358055669 04873-01262600355C-44575793595-04132385911-09005980512C-45 642183-0318915203206563382699N-3456802836306214272976091949 94026N-30317549257-00275068055-11305702198N345311850360664 6365221-07967749374N29295641231-037919150091057935546O-315 515528831003269604720686284305O22944956876-0503152581321259 015519C47546217676-2005312938513754499978H58222177069-2165 292051312610324285H44981298478-2169311775724149474487H4226 1421432-2736787026307804757124C5042012989040679759121969700 01H469024295220185632170729698413765H61212987387031070241 19575087046H478577499941435468234717423363002C45074348829- 13918744535-14827167221H44632125158-10024668086-24911916891 H53669066502-20472203296-13969597701H36077070853-1967835335 8-13020499392C5915332403405600236898-08038365684H677271946 02-00480906464-05312555387H5965013712207833604213-185928237 31H5964878369914959152806-02649888883C-42397909022-1634659 580413776220578H-41683711808-1441341208924411444962H-50215 174824-2367562447412151606193H-32970197229-2053722137810475 667768C-587834215210244367579111893420839H-66994797709-041 8501766509353084105H-582510743740317377016322685425762H-60 9172173291228951434707969980821C-47067966954-17956834098-14 932137678H-57241042886-21076139992-12762875204H-45737138021 -17511257616-25641410357H-40222729752-25366760709-1104982504 C-5289923877706305263043-16552583246H-49808984517062824070 64-26918341238H-6345419559303890776612-16021352138H-514161 4661116285629752-12585530839O3443416548913905972725-1839259 56O-25098065612-02097994198-22684508009Br-00395881388-1393 7535802-01622901292Version=IA32L-G03RevC02State=3-AHF=-3862668 3728RMSD=7747e-06RMSF=5779e-05Dipole=-02982945-0406445514128 67PG=C01 [X(C20H27Br1N4O4)]

(b) Molecule a5 (with cc-pvTZ basis set for Br and 6-311+G(dp) for other atoms)

11GINC-PAULINGFOptROHFGenC20H27Br1N4O4(3)SND10-May-20120P OPT ROHFGEN GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=900)Title Card Required03C-120007824251201239589301238389594C-116371245 342568492648603547742488C003715679783242941880504244306352 C121647620172540561907402916129292C12078248236116534245310 1072130895C-0007661264104973122140001917056H-208911228673 103324317304630693901H215948969423051805443803176132773H00 5424123144305947818605756328728C251714139640487834236200255 521648C46140781859-01330481628-0673331335C44164559891-0685 660586707745564841C-252678812520561838161800209763555C-447 87604319-03209282777-08081170767C-45481906822-0396133969075 21738921N-34325867260509994365210894732279N-30587043255009 00202402-10282671827N3429182568207658537924-08112515435N29 577256629-0501751694209133702804O-3103173646707646191718226 58489052O23538476336-0760013752319753971181C47878837349-21 5232995909712773857H5851460312-2294867481808071509083H4560 9029819-2445811056519888989837H42411757825-2804237673403045 61204C509766880760166607366618547182024H47718168031-017629 8307828289557049H617579747330071536220118013530988H4840097 17271215860823917633730039C44628415975-11857616604-17784930 525H43867435486-06732845563-27283507091H53258516841-184169 4332-18017141527H3570349464-17853077303-16442747836C588996 1193506701112847-09000271523H6754343796900349504009-0730698 591H5909645318210248149321-19198999332H5955546264615308146 405-02491261646C-42106438133-17821840051319443144H-4112301 6049-1704366309523954501039H-49985645796-249291657691098794 2532H-32777447543-2164162579909229768258C-5847898374601065 59738313738314791H-66765606638-0524904090110693172527H-576 911435970062752363624530442369H-606787482571127730700910950 779842C-47431401782-16316707248-1540806561H-57554005521-19 666693707-13350413987H-46352265377-14715111023-26034791946H -40507236535-24094714268-12510988252C-5328328163207965562387 -14256694313H-5042813560109079498573-24629794316H-63823322 4605480424179-13754585285H-5171129490817458764074-092622046 96O3389689707816157073137-17549341482O-2563277022600324390 88-21916800068Br-00448085155-13586519283-03421852526Version =IA64L-G03RevC02State=3-AHF=-38627624959RMSD=5212e-06RMSF=5040 e-05Dipole=-02756259-0574838213526555PG=C01 [X(C20H27Br1N4O4)]

Job cpu time 0 days 9 hours 23 minutes 128 seconds File lengths (MBytes) RWF= 398 Int= 0 D2E= 0 Chk= 40 Scr= 1 Normal termination of Gaussian 03 at Thu May 10 234808 2012

14) Molecule b5(a) Molecule b5 (6-311G(dP) basis set)

11GINC-GINSBERGFOptROHF6-311G(dp)C20H27Br1N4O4(3)SNDATTA16-Fe b-20120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXC YCLE=900)Title Card Required03C-1525880677808010644892-003 07679143C-143739237742189490229200479042133C-0207912160528 07331393201322471036C09515448652052597913501397351256C0887 20405130671064344700380184239C-035318545400556169819-004154 39779H-232074797512792379942600559504H-0149157704238758600 46302009237741C20792644631-01948908057-00074249591C3916664 2811-13520611669-07541176159C37031332791-171924982550750375 3397C-2825619321101189150313-01240734131C-44821258095-1390 5685776-068024715C-50988857768-0364709392603141659061N-405 640894050681459421702648633975N-3033861613-10479742706-0592 471343N29472263192-02286126947-09310071362N23352498496-119 679099570937982214O-415084975291716334497209560246853O1734 3976186-1261779348820294674284C37511896582-3209761797210730 892215H47419233686-3604358764408704110094H3538472824-33553 9892092124997587H30271413265-3775125889105032844691C462793 4779-0955103634217084947376H43028550334-1135688071627259721 367H56522534504-1295669750416116003135H4599577320401132140 34515299034538C34659244798-24382505533-17387338704H3446875 7437-20108150869-27321317898H41571846841-32734068868-172823 61125H24720712309-28045797117-15087440081C53168497406-0872 8525936-11204485102H60340195646-16674588403-09371464962H53 393362614-06146272407-21689787759H5610915263600019167341-05 575252669C-51731328614-0876706975817598783649H-54445930785- 0053991977124097963735H-59247668413-1651042456218571778463H -42228840367-1274379467520974009338C-6450052813202141571828 -00941266256H-71976252431-05721111069-01249983335H-6763180 17690948564472406374178533H-6413034909706970901635-10606737 674C-46829033877-28573267716-03145707373H-57445724031-3084 9168275-02969870718H-42038227989-3478537783-10566665256H-4 2562249504-3101835619506481157168C-48741506661-11653801457-2 1462897985H-42273376212-176939865-27683222867H-59027528974 -14624357451-23168087428H-47574676657-01286703593-2440676867 O2997394008704838837752-1975982674O-21840510076-1862775864 6-10827478165H-04116756243-10083981881-01298015316Br259902 405322958619865603404485604Version=IA32L-G03RevC02State=3-AHF =-3862680414RMSD=3356e-06RMSF=7225e-05Dipole=-12419503-103748 2208000603PG=C01 [X(C20H27Br1N4O4)]

(b) Molecule b5 (with cc-pvTZ basis set for Br and 6-311+G(dp) for other atoms)

11GINC-PAULINGFOptROHFGenC20H27Br1N4O4(3)SND12-May-20120P OPT ROHFGEN GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=900)Title Card Required03C-1487236590608648647891-00950681132C-13332011 37722474296351-01758301182C-0075100769328110220423-01789990 091C1049051339120077884078-0101817484C09178855321062807211 25-00420542699C-0350746392600675067491-00341704963H-218756 6355328889463663-02256540713H0033938466238765006024-0233430 9742C20679885515-02930965983-00049558175C38404474853-16071 288-06420382914C36291822765-1806959687208939256253C-281838 480790239673805-00983216367C-4552124885-1238265371-04731882 786C-5104462748-0084893103304135093111N-401522107408988045 96702416789556N-30881603029-095902815-04366859061N29221998 662-04631470844-09262320048N22897588915-1202691420510376041 526O-405046081342004859440208187325812O17011645725-1125710 10521350393615C36109090114-3257176218413679270712H45788579 859-371815270511979369969H34062808086-328381163192431123513 7H28529510476-3842063569608659260811C4601493439-0994402949 917608002872H42811305926-1053392655727939576454H5607104465 5-1392653655316917132219H462195837680050034298314730869571 C33272152368-2766362312-15053524062H33179184313-24440526232 -25378029894H39774363707-36288821718-14119000238H231940097 8-30575194332-12325693932C5256694872-12355759627-1067019398 7H5938613218-20394059179-0805907797H52784178253-1090562900 3-21371225266H55977553812-03213245356-06018158916C-5179296 265-043730532411906118357H-54009511341046160989532468078603 7H-59650353199-1159504225120933324106H-42435708065-0843041 245622732906536C-6433484187705121156401-00389924431H-72174 273796-0236035251100221366869H-6700097015133395028206137624 107H-6389479390608879189916-10517326627C-48164933035-26471 49148900468468991H-58873332422-2820150087300981217249H-437 78115761-33650605054-06301065785H-43880402996-2809768218410 259017005C-49549722324-11490841156-19508479997H-43455659667 -18443280145-25124302679H-59984504583-14136802836-2079246188 5H-47954087457-01553601781-23534463648O2991155009401346540 74-20405978156O-22849201003-18611037362-08460795112H-04602 345551-0995581613100007078012Br2735927735528488504706-00305 729919Version=IA64L-G03RevC02State=3-AHF=-38627743362RMSD=3061 e-06RMSF=7089e-05Dipole=-12591126-089061760913402PG=C01 [X(C2 0H27Br1N4O4)] Job cpu time 0 days 11 hours 37 minutes 120 seconds File lengths (MBytes) RWF= 398 Int= 0 D2E= 0 Chk= 43 Scr= 1 Normal termination of Gaussian 03 at Sat May 12 011620 2012

15) Molecule c5(a) Molecule c5 (6-311G(dP) basis set)

11GINC-DAVIDSONFOptROHF6-311G(dp)C20H27Br1N4O4(3)SNDATTA01-Ma y-20120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXC YCLE=900)Title Card Required03C-1145730027605596570337-011 23669244C-0980261045419003009856-0447619791C02934288541239 48738588-06331840605C140975910941598351004-04864415606C124 1610986502644738168-0124112914C-00333397362-025755530330049 3613161H-182506130172545221806-05637010046C24223160731-059 82040450035223889C44705797756-15969967977-03050239269C3865 5966042-2199958725809980379615C-2492216428-0009729003600512 518597C-42950288832-14446944675-00409145049C-47335867333-0 191867870107742442594N-363082468080727188218904230189416N-2 8250872339-12211071648-0154406588N35363043778-04645399687-0 5648210706N2469170444-173536561720860273483O-357059924021 879484183509003456543O16244733883-1958009280517540525785C3 909175846-3721665120810985692241H49386671335-40642498774113 14375708H34198090196-4035501648520123347447H34083702644-42 00234471402687234493C44364681846-1582315786622826035961H38 508014298-192408975513127009722H54648455735-188807084122434 2194639H43988901955-0499063161722616981905C43637923473-251 0848705-15327401042H45943811711-19261621799-24132055983H50 694135969-33308362551-14610705396H33658695852-29182516657-1 6467647311C58948076707-10663085755-01823496037H65642844838- 1879102036800830032176H62034285333-06537764445-1131466145H 59794283824-0286027824405610667387C-46947988142-04023749199 22946834164H-48409448782055228623382784831418H-54841690548 -10734621626118288714H-37447336786-080850568126225549411C- 607576650820413918231303754223994H-6876298982-029225574240 571723971H-625853425761303384929209654725173H-610514281690 6917993275-06689314704C-45557658889-2787880738906322457642H -56229966426-2916112882207865882016H-41961447994-35813515924 -00059741352H-40510925154-2874124328415843182126C-48216361 574-1478060676-14813966251H-42865204705-22473928903-2021676 3922H-58804702645-17103525667-1496151984H-46650746164-0533 8273931-19903226719O3865257461804248529241-14181163139O-20 857094411-21824223791-05480822895H-01775276556-128700568302 894325597H2391297407919835541657-06647080031Br051355645954 2200101026-11131223867Version=IA32L-G03RevC02State=3-AHF=-3862 6892039RMSD=5937e-06RMSF=3444e-05Dipole=-0892166-14768884117 65922PG=C01 [X(C20H27Br1N4O4)]

(b) Molecule c5 (with cc-pvTZ basis set for Br and 6-311+G(dp) for other atoms)

11GINC-PAULINGFOptROHF6-311G(dp)C20H27Br1N4O4(3)SND15-May-201 20P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE= 900)Title Card Required03C-1204359732404322554957-00304747 268C-1202133505918239430089-00118266152C000267897712494440 748900004665853C120714495861822528330800040087204C12008220 114043016856990012962156C-00015244537-02637489779-001788939 44H-2118855435123741313804-00089381632C24771599354-0301021 389600158456437C46428400564-09344113546-04505116489C408859 70433-1915868098806251456326C-24713844083-03130153121-00868 584561C-40758018052-18771962443-06317059835C-46879718615-0 932377147704447858908N-370240232020167708775903940079418N-2 6435930205-14628296152-06053689497N3579064926801100320091-0 4696526351N26481920213-1597635457405312081294O-37995417427 1160060753311456191993O18174210029-2138280513412924236314C 43223705606-3397138822103443946437H5385912469-361434387790 347268815H38551585-3988317333911223071899H39061303996-3703 4362975-06050268735C45459190797-1583645988120527232116H398 93079188-2196028625327512850301H56011432729-179471541322179 1726896H43707191915-0543118176623015464333C46814968492-151 10353713-18717287642H48565045127-06983871524-25639943429H5 4835856604-22339690324-19689490183H37462545475-19895852903-2 1384609847C59851127806-02903616148-01210479768H67455282365 -10602895308-00303280309H626163164190383014268-09187817744H 595252289920279561351807970086768C-46579357769-15160195103 18646422642H-49394735549-0742114352625680461829H-5359857578 5-233592810781959982346H-36708743074-1874301127821337549334 C-60863530529-0405727956601371773112H-67954424286-12269214 22301071067579H-6393894907602768753409195893023H-612629157 2301232300703-08048291937C-41806840837-33682295348-03299370 08H-52265273718-36545921539-02711303495H-37087536492-39261 505086-11250755532H-36918031066-363427089540596778449C-455 98523836-16042537233-20616061952H-39204352906-21449083329-2 7464093084H-55808623873-19449051262-21912233046H-45100866265 -05503166577-23102923509O3812786390612197161787-10538990815 O-17797915986-21995897316-11856966099H-00197988761-1329957 6705-00499852201H2135913493523520642551-00195973231Br00011 4210144394451036800028241349Version=IA64L-G03RevC02State=3-AH F=-38626891993RMSD=5275e-06RMSF=6255e-05Dipole=-07248272-1823 475507198299PG=C01 [X(C20H27Br1N4O4)]

Job cpu time 0 days 7 hours 1 minutes 579 seconds File lengths (MBytes) RWF= 363 Int= 0 D2E= 0 Chk= 43 Scr= 1 Normal termination of Gaussian 03 at Tue May 15 013222 2012

16) Molecule a6

11GINC-DAVIDSONFOptROHF6-311G(dp)C20H28N4O5(3)SNDATTA08-May-2 0120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYC= 900)Title Card Required03C-148744130908021576619-027310382 43C-246786072840678595896-12311324722C-23254871555-0207572 1034-22904996342C-11950417441-09829896971-23605567606C-017 68629897-08668832484-14101125351C-0306890265900536020633-03 603217744H-3355848059412793220777-11518256206C10007128952-1 7341481059-15092615511C31769545495-25083333616-15369862509C 22298378785-37459853687-16202419462C-165993290917284761235 08578525534C-205911880912581672088529502952346C-15139095771 3742787421520576078118N-168389759343123933901807288947265N -183924919521398625526520677600585N22035181716-14294410819 -12355021454N09609704368-30609176627-19563548944O-139409684 0237110408766-0332771301O-0109997193-37012919308-2078900632 1C25816799018-47692941571-26950851751H35446211767-52206892 949-2478534154H18362651758-55549922703-27019692162H2617368 2174-43304249815-3682513472C20288798327-44571875421-0274524 7453H12317369045-51834546125-03760105615H29297274182-49801 76165300236116198H17545937658-3764365316705126143531C38337 902049-21244739506-28692621114H4280369048-11451636835-27607 825461H46080931453-28357508015-31335083848H3111502231-2079 7859657-36764389557C42366280072-25686471456-04411912973H48 979895715-34110956416-06193799509H48189551405-16588438312-0 4588984947H38024679134-2666791949105439551568C-001473662974 0131319922508924665H031666491824702988239914839018118H017 78380184460495111632192491839H05696033231049500161216321256 04C-228881132315053821763921419647747H-2213802934546826636 4231425009967H-186289913095767877258214480001878H-33340335 085492884223518947066229C-13218028412369462360342678985315 H-141263149663258483530848853572116H-1762132958915323737215 47894484736H-02742304889215042581741168702057C-3570144123 2636894314332051001688H-387770571051689694943936276558448H -381361822843429574014239037557782H-41275769538279771701772 289127125O2642562392-02594152288-08736270265O-193914448580 228889724725503841454H-1087837132-16902615617-31589836963O 061604420730233924793405639868568H150390909620146273881401 668342297H-30943830309-02966008341-30341056464Version=IA32L-G 03RevC02State=3-AHF=-13657967653RMSD=9590e-06RMSF=7957e-05Dip ole=07452199-05474204-06200523PG=C01 [X(C20H28N4O5)]

17) Molecule b6

11GINC-DAVIDSONFOptROHF6-311G(dp)C20H28N4O5(3)SNDATTA22-May-2 0120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYC= 900)Title Card Required03C-129754792420889865568-038716569 37C-2127982100609655099254-15081995326C-189399833720121285 3172-25868667232C-08490845164-07697119401-25701165201C0010 2110577-08320879427-14713648749C-02297593759-00025693284-03 884391821C11601173119-17413627433-14441465733C32684007262-2 6080853162-10976066922C23752671854-37547521631-16585082154C -151631069341679380600208370658368C-1723965289622765290228 30617855863C-161313344823590794218922310610989N-18497076368 304169539830882535255N-139786904281245652016120306651971N 22532235233-15554839017-08186907047N12329702288-29561802158 -21476875471O-1973814470637582640699-01240055572O0242996371 2-34962947798-2683512391C29848736233-45647584769-2798471185 6H38660300814-50940113741-2449670069H22662230797-529747375 63-31441500178H32622991276-39438609505-36390193395C1844452 7032-47066298706-05768071844H11002188142-53584001244-101809 69063H26425387557-53211299918-01770167991H13796781111-4168 977061702414974381C42316951958-19977596866-21236805787H462 77070007-10792218839-17118222562H50537540934-26743237451-23 293199996H37314626435-17636032137-30565730838C40265587595-2 937969601601838535819H47119592962-3760557380100013520959H4 592309168-2071936969504941420325H33631782376-3206695740409 939383061C-02073707944208399998522267834898H-0176965032250 00365122114884523107H002881244924632825865531953339454H055 417463523480399890319729844141C-264712057944664047971625567 411154H-25122690115006973027935774292627H-2510820763955092 00348818944147596H-366083238284306288076524414617612C-0744 4569075215693049442242219829H-09296819795295471977434937359 5983H-088949744171206506209547159042975H028528749512208088 99438995594166C-314293754591948097623435420217198H-3151888 30060928906920139043676403H-3435956068326099715611434902041 89H-386974316182029881295927418709365O25919897078-05434327 229-01123073473O-113167333670068125555824071314116H-069681 5322-14118083654-34137175393H-2551399030601897065086-343240 36189H04109168584-0054956439104644994468O-3183171453617850 242184-15955241856H-29790697126289275681-12167780313Version =IA32L-G03RevC02State=3-AHF=-1365790765RMSD=5731e-06RMSF=6414e -05Dipole=051265820323464905910257PG=C01 [X(C20H28N4O5)]

18) Molecule c6

11GINC-DAVIDSONFOptROHF6-311G(dp)C20H28N4O5(3)SNDATTA28-May-2 0120P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYC= 900)Title Card Required03C-1228406211509302540548-02187475 392C-2059973594810541094807-13196666511C-18484223102546066 284-24298533832C-08088896273-06505081487-24493571315C00364 622436-07586389984-13467600475C-0171234816300257589461-0224 8801142C11622928101-17057452715-1366054937C32523430283-264 2531128-11002289767C22991124202-37596696886-16194052621C-1 4585031931175450169909785737781C-17153673522242129033683168 3585957C-177454991733698218441422769689487N-19659787853065 130914409562462935N-126820466621394433332821836635196N2285 2948317-1551053555-07869281661N11679880576-29238374849-2069 9096543O-205016200137452303911-00876901082O01465774236-342 68087937-25786763403C2836637022-45949444166-27772691242H37 119568546-51523359468-24591850992H20807225864-53041035312-3 0909469887H31027732251-39876296308-36313678683C1776362641-4 6876817795-051326704H09935041726-53142198938-09231385472H2 5668480409-53283738052-01406215148H1361997371-413088862103 191616506C41943619235-20689988894-21662574267H46411567249-1 1654420428-17739253258H49812711966-27763920329-24025352297H 36657331658-18182020054-30789717689C40471474951-29918759346 01534977199H46942935235-38398579519-00505231496H4655828968 5-2145843169304360372394H34066128684-3232222352509902973955 C-045226831624477413800522301808082H-052193455452395836073 14637234977H-0256061013349635240102317862242H038724336413 834652593319916368917C-29230232355465617084762578192055H-2 81290676625068461261635762689569H-290256329325475647764718 705192743H-38879213669417387684372505365522C-0726363547424 77573403143276275538H-10068387417327719416555007008164H-07 5062237741538882875548610573724H028823371752641168128439925 066557C-308084762671941655062536766836595H-296184825750945 653736340816163882H-345073251042596809934144574032151H-381 531597841899375709628803640547O26857740994-05578615471-0101 0672605O-087104542080262720850526121735805H-06609971194-12 737220492-33098377945H04692366622-00619675014062428172H-28 66700396217580064677-13393844901O-269751875304070393471-347 084628H-24968879331-02026616712-41580982351Version=IA32L-G03R evC02State=3-AHF=-13657848681RMSD=4503e-06RMSF=6836e-05Dipole =03051947-03692794-02302358PG=C01 [X(C20H28N4O5)]

Job cpu time 4 days 6 hours 10 minutes 163 seconds File lengths (MBytes) RWF= 376 Int= 0 D2E= 0 Chk= 39 Scr= 1 Normal termination of Gaussian 03 at Wed May 28 042024 2012

19) Molecule a7

11GINC-PAULINGFOptROHF6-311G(dp)C20H29N5O4(3)SND13-Apr-20120 P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=800 )Optimization03C11757270972096804781-04156412691C118889 189722318042119-07470027244C0014582152430355273139-08382608 546C-1187996662324210020078-05476182009C-12170473297109695 81125-01451189102C-004425616503419520603-01184641177H21223 46470428042308584-09516328496C-2527112726104942962756019299 50226C-40989629733-08035544931267689395C-47280348846-00641 26740800425592754C2461465807702491465207-03657983429C41140 791023-13547989661-05245388265C48040159323-00009813791-0165 2883277N361288574640774378242502303137029N27306665953-0898 1936271-08426562049N-291146105060052253078314592464628N-35 05618737404646429083-06125073605O36726553647188697471607872 073177O-3569996177609650121117-17985454024C-54981868247-09 37806424-09408123783H-63464843027-13963414695-04405307724H- 58595816593-03232000552-17527768623H-48795178419-17154460957 -13670950769C-557385061261158414624504213586517H-574894125 8217391325565-04750271324H-65296966254085253675810832550045 8H-506832156171785122363711466163945C-36830254936-22460633 20209388909625H-31392491334-2668040129817755622178H-455714 88967-2863947379307712369634H-30527216971-23031317265005884 7591C-49525136816-080232447625321744262H-58776436234-13479 76784923693293081H-44097918966-1291834608433325539552H-518 943612050201128356328564505052C5440025104707090015924-13687 160108H5734678146417079134522-10684006397H6323381401825422 237-17102442207H4748781666807945262925-21995161936C5806082 2476-0062518474709830508798H66372801449-0706157971507137436 48H619559618930928658618511771026955H53608060151-043153692 9318963832223C46969989142-20843665406-17298712491H57322224 48-23440481622-15302244528H41363485732-29906846154-19047421 834H46519968872-14890640346-26309437678C39798587322-232607 3704106547139394H33236267801-3134668100303606766706H494492 14192-2742178881709198215942H35574199975-184404449411529132 3458O-19423843093-0431093606722943638772O1930004356-169724 2745-14551800508H-2112072792429579878316-06367305493H00371 19140240677471004-11335252113N-01525073863-1007745360902267 157942H04873985117-15520438561-03461735695H-13877442287-10 22375123217991955874Version=IA64L-G03RevC02State=3-AHF=-134592 21208RMSD=5365e-06RMSF=7400e-05Dipole=23562205-0447495208633 099PG=C01 [X(C20H29N5O4)]Job cpu time 2 days 0 hours 51 minutes 296 seconds File lengths (MBytes) RWF= 387 Int= 0 D2E= 0 Chk= 42 Scr= 1 Normal termination of Gaussian 03 at Fri Apr 13 103926 2012

20) Molecule b7

11GINC-COMPUTE-0-25FOptROHF6-311G(dp)C20H29N5O4(3)SNDUTTA03-A pr-20120 opt rohf6-311g(dp) geom=connectivity scf=(conver=5maxc ycle=800)Optimization03C1225124095913229837606-03287171192 C119614840532690772135-06324341881C-0051101282333105481119 -074521624C-1218448493726097989971-05709410191C-1193209000 312434482481-02877649627C0040440991906205872758-01656147665 C-2420879838604622440617-01268401058C-39638429488-12511318 448-02059152377C-45852218225-0098775286806377930271C247478 7285405772148499-01016287137C4078954541-0767594667108685299 902C44762713301-05658643401-06256305598N358463942070561078 2869-09616495658N27041405673-0187856509108896770769N-25587 31318-07841665438-03500081647N-3659127437909938690896027693 47632O3593301585411099733291-20777461274O-3790688761821401 43243407530624541C-601887147160279714570278741836H-6685594 7331-0552609449504811376061H-633303416751119040592908867582 018H-6119835010505611353401-07603262722C-44745656053-03166 64031321537433453H-476403603370595591746226610798075H-5134 1895125-1112567427124790540779H-34624434926-056277224872453 1643641C-45177699489-13598712229-16324272401H-38727367529-2 020256446-21962252911H-55217808619-17695646344-16255522934H -45374383486-03975391309-21313594121C-39795869207-262559091 0204550429786H-50057026917-2933540214906342346505H-3508167 0913-33406178693-02027919433H-34413456241-26345137054139244 32658C40875014927-17412315418-15339100561H42315798493-1447 0927321-256640082H47096394914-26056226188-13337251345H3049 500466-20250548027-14059028723C59327252785-01851673384-0872 507522H65856119754-09923638508-05561427221H6087583388-0020 6696468-19314361636H6215689609207163114382-03467195102C402 66522693-22169296811133925507H50124441798-26639902075124983 37722H37217467838-2243592055523748625682H33207011714-28066 3396607716052839C48964843660070553578418593645984H44038061 2840034048996728217520306H58994767573-032802847411962822659 8H496175091381107926615715515057044O-16784654279-160666331 65-07865205778O19541463473-0418970252818868017805H-2151911 737731272428336-06594123494H-0092249046243609118908-0972377 0565H00785366466-0420991913800693332811N235037230934421851 4-07513751181H308556508829992186296-1256155742H21929765887 43691007399-10780103771Version=EM64L-G09RevA02State=3-AHF=-13 459555257RMSD=5516e-06RMSF=2203e-05Dipole=0281197601258436-0 4782948Quadrupole=245428887-58810793-18661809514853901-1548 5167-5179032PG=C01 [X(C20H29N5O4)]

21) Molecule c7

11GINC-COMPUTE-0-114FOptROHF6-311G(dp)C20H29N5O4(3)SNDUTTA11- Apr-20120p opt rohf6-311g(dp) geom=connectivity scf=(conver=5ma xcycle=900)Title Card Required03C-1192216510309811823279-0 0528910749C-1195037867423692153764-00537607322C-00016081491 30754394367-00159151269C119334767682373059152400227899242C 119336567260984025898600387940075C0001614037202758421917-0 0020208369C246356784650243232252401054695908C40858417043-1 289528067206810009372C46434121281-0433480679-04949375442C-2 461692560202386820484-01102336726C-40846670251-12991483205- 06703983592C-46443326779-042795019350493318773N-36707173369 0681954473204567390413N-26556970162-08742944952-06961715462 N26578060112-0861892217707060083693N367226388706787676158 -04676042225O-374226502851637982915412553533473O3743417843 16260993149-12771075314C6062267542200946996889-03072023558H 67641541548-07318290874-02578858203H6330327044107148208674 -11535670436H616216680840689633498505901037024C45253732372 -11178598061-18644824108H47665318693-0398273417-26373658513 H52171789535-19483134683-19427637484H35223466464-1485641365 9-20470696091C46544123299-0920245539920569598213H404770070 18-1398378186928141625335H56770819256-126689185532154929341 1H463138368380149975850422286444625C41602867383-2799774317 04831568027H51984159613-3103547383103847305853H37301250513 -3292404984313425023702H36146944448-31249903894-03914653335 C-45324984861-109639873641871217942H-47753834024-036748510 126347699713H-52259779477-192473161919565640914H-353078071 26-146379593220616759545C-606135333770101038433302942781578 H-6764763847-0724570718602518758446H-633121795910731398555 711324828213H-6156612613206857775564-06101701513C-41625491 31-28067542079-04546771471H-52015725534-31074040419-0356132 962H-37305687258-33103448554-1306712741H-36204140365-31226 46674904255071182C-46479934167-09451880951-20525649571H-40 401709083-14339442799-28020380593H-56711825909-12906241654-2 1494237563H-4621640859201227311415-22373612513O18267487447 -1542360771813902096295O-18237201437-15649885291-13676693098 H212006208032912511339500300218882H00026658627-07912206138 00057239091H-212211875872907151264-00813238531N-0006787677 344738067768-00732319953H-08214825568489029283503207845599 H08162042484489678430470295168506Version=EM64L-G09RevA02Stat e=3-AHF=-13459510483RMSD=8337e-06RMSF=1761e-05Dipole=-00034412 043900830422463Quadrupole=25981594-76465641-18335029901303 452191289324577288PG=C01 [X(C20H29N5O4)]

Job cpu time 0 days 7 hours 59 minutes 532 seconds File lengths (MBytes) RWF= 385 Int= 0 D2E= 0 Chk= 37 Scr= 1 Normal termination of Gaussian 09 at Wed Apr 11 114331 2012

22) Molecule a8

11GINC-PAULINGFOptROHF6-311G(dp)C26H32N4O4(3)SND05-Apr-20120 P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=900 )Title Card Required03C117944941431480641297201494543792C 117475414682865872544401396915786C-000534536535609156728-0 0290618008C-1183495482628596717458-01862619516C-11840133114 14746049536-01731724777C-0001237566907578914464-00058980853 C-2489043244207884913648-0306224595C-44180714073-010193686 67-11769583638C-44419901514-0339217011303700268119C2486912 5611080138403302935357281C44216650093-006248590921176794325 3C44398496233-03355625508-03640779996N33493425937056729797 22-07814591214N302831645810434588339213771644575N-30279143 19504011354585-13839180786N-3351340272605704636539077204530 25O2995410414506974164225-19719923543O-2998567475107219909 29819604354525C-574161082450047988131110699042998H-6555097 1267-0581398909507228574286H-56315253038-010110831782136910 6571H-600608556241082822825909021287539C-40408137284-17618 34101107841707986H-39163123062-178881488581860007927H-4810 4862845-2475037082105118336615H-31062221266-206762362630330 838878C-5340404360810246646238-1658741586H-508496417221258 8245636-26835440519H-6378674403307154505224-16167725688H-5 222310467819240368606-10648989375C-46388360022-13450253604-2 0318708308H-56297168598-17469875118-18423974993H-4562834256 6-10756525024-30751786793H-39054226999-21134868875-18320926 907C40333415702-17661664637-07441164875H39113339661-181898 45293-1819278463H47991881519-24758447314-04524247068H30963 37253-20566368877-02858028844C5737699979100325192079-107739 58546H65513116139-05897455218-0718011742H56238101034-01419 191473-214014486H6004401433210706475391-09353276437C465648 27787-1283100828220598427576H56487673021-168301062641873362 8727H45855971166-0989191738430968672764H39269265009-206094 2185918835689411C533640906471083131071716271037818H5093650 9211132966597212652082725H637789031850786715422115736997635 H519742876611971662408410215620922O-255414486460484102444 -25667235849O2555881921053644641442559006627H-211059663013 3867573498-03190165767H210034259463397720576502637059616H- 0006970889446349953091-00379979472C00004971558-074008238520 0064802336C-0283667057-1449073925-11558498621C02879636427- 1428619724811803384177C-02758834718-28346746345-11416742595 H-05277302925-0917270099-2057256313C02852936578-28142602279 1189369133H05305585215-0880956170220726527655C00058428322 -3518954155700296482931H-04909041607-33754734224-20461457891 H0502526885-3339122972721026640093H00078141342-45948309339 00385722931Version=IA64L-G03RevC02State=3-AHF=-15204920304RMS D=4817e-06RMSF=6301e-05Dipole=-00003112-0776789500055228PG=C 01 [X(C26H32N4O4)]

Normal termination of Gaussian 03 at Thu Apr 5 014757 2012

23) Molecule b8

11GINC-PAULINGFOptROHF6-311G(dp)C26H32N4O4(3)SND19-Apr-20120 OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=800) Optimization03C065860846330602660576300985454031C066920 354361993978211801405275886C-054964655992656424425700430167 783C-1739192766519675589067-00655173138C-17446388196057492 84787-00879379734C-05294079071-00970327239-00175604592C-29 949293532-01897701368-02039084641C-45343958414-18175693303-0 7614859284C-5245511812-0805159167701822832671C19029126264- 0199400593701046312987C3676843256-1507945113707530002992C3 530698799-16358516918-0800701342N26229289472-0500697635-10 537002425N243660045-0755713817311086056623N-31150791315-13 804076926-06425861646N-42707815381030372753601294128021O22 35963114-01802438355-21960154182O-4453727632613521183397078 18487417C-66179790318-03273136394-028192803H-73126798301-1 160851214-03092721394H-699932563180406612920204170378906H-6 582697512601283582284-12617403653C-53309082589-127805133821 6406785292H-56733498065-045555995552256537698H-60345785143 -2095937282917411176065H-43679365329-1603272727320172481428 C-48954947966-16613111959-22443734307H-41912460103-22386248 052-28282303878H-58967604909-20305298336-24359044577H-4837 5701183-06279458164-25667809202C-46535094587-32829320201-03 564624987H-5698630805-35780789747-03628521454H-41126815478- 38932061569-10644291461H-42422859092-347115308606253815444C 28094248746-29142618132-12515069506H26005005989-28417176136 -2311979392H34271808624-37889089849-10834284164H1867016060 1-30525964771-07346221509C48229040554-14717967619-159519723 H55145112995-22730707417-13542818021H46011599848-152434834 08-2653941337H53048864042-05238955221-14006204188C36956960 985-2827534859615178552057H45584711542-34133391784121489084 54H37647744357-2622092688925760518744H2800646203-341064122 5513517138711C48530838656-0635672621212051036015H474728132 42-0442786197722644462396H57931792393-114902335841036279058 9H487514983530314857205706868448351O-21999933003-215410884 11-10855752349O20847890183-0653296607723331546398H-2656602 637625155463319-01166366686H-056605203033729840899200798488 337H-05201417277-11649672638-00710997966C19249888074278131 5713803126426436C2286204987137463203633-0621151284C2724307 99632587496322414340943923C3428877973145051887901-043954456 65H167986037243891773939-14971546819C386330716493354978747 616160973529H24532684062184005719921590251401C42183307448 4313486885106822704207H370183271445242973713-11728027672H4 4689808943204601539824920164027H51032367253490740780310827 0829227Version=IA64L-G03RevC02State=3-AHF=-15204982924RMSD=465 5e-06RMSF=3314e-05Dipole=-04566859-03330795-06464858PG=C01 [X (C26H32N4O4)]

24) Molecule c8

11GINC-PAULINGFOptROHF6-311G(dp)C26H32N4O4(3)SND21-Apr-20120 P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=800 )Title Card Required03C-119827881920125350109400175462973 C-119362065991515155752900032596793C0000036892322230109748 -00062126185C1193994763615152798949-00111967862C1198848513 01254787311-00162884275C00002050897-0574623361900031308877C 24629982781-06271047583-00363009659C40132760527-23083872489 -0334010848C47825019035-1040477510801483447312C-2462742814 4-0626599052400416156419C-40149406042-23034303503527325418 C-47812439151-10417865358-01505761823N-36377347007-02373425 099-0616851113N-26638311392-1736127397906329803753N2660746 4098-17444308763-06143097001N36416170726-023001006810610326 6216O-3768840538608161935866-12646320108O37750556686082690 8323612519416365C57708269935-126867582641287696906H6564083 6658-1933749781509613349142H62168175644-0324914711115747375 08H52968440496-1693975078521612155016C54715648573-02646519 778-09836098953H5820491014606843124488-05931025242H6325880 0048-08101922602-13671649943H47941000763-00646014855-180595 4515C3803999532-3371147261907520451367H30812989165-4090002 461803897355897H47332011546-3886177100309689553625H3421257 0486-2939942831316699151862C45615698412-29633635603-1596747 1344H55762803968-33063114959-14170572537H39449900856-38115 461059-18546282088H45637692504-22880704839-2441022127C-547 67990937-025142276409672200086H-582409435080692041893105623 119002H-63328407943-0792419340413533497264H-48038923992-00 4008797131790514673C-57632181199-12846433583-12925327634H-6 5587220254-19450943341-09622165302H-6207063578-0344461308-1 5942868296H-52844052279-17213971748-21577100723C-4569935762 8-2941329757716212339913H-55832450625-328785288361440419433 3H-39539774967-3785152895118943908518H-45777988099-2254329 010624559869383C-37997535365-33807980625-07176972181H-3080 406069-40955922752-03410379065H-47281675652-38975117822-093 39578392H-34102949114-29622916491-16386090495O18326696916-2 4359563867-12919939607O-18391846556-2418851548513233683945H 212022754132052765059500096911222H00006099396-164254105560 0063658964H-2120123400920522078112-00213383674C00000407775 37146106899-00109784868C-08019049567442923163108731628514C 080209866564423442499-08997062087C-08027772642581311098930 8682389184H-141381037823900744016515820845956C080318366065 8073109524-09037098885H14139436742389030325-16051731774C00 00243917265076833773-0019983889H-14249937279634746584156397 51757H142549098863370869332-16028584999H000032045275829670 963-00234199172Version=IA64L-G03RevC02State=3-AHF=-15205003814 RMSD=2881e-06RMSF=8934e-05Dipole=00031240228309-00102894PG= C01 [X(C26H32N4O4)]Normal termination of Gaussian 03 at Sat Apr 21 221901 2012

25) Molecule a9

11GINC-DAVIDSONFOptROHF6-311G(dp)C21H30N4O4(3)SNDATTA03-Jul-2 0080P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCL E=800)Optimization03C-001907106623067053057602111644826C 117670658332382670655801945750407C119838772270995120325801 169212566C001575493260253501070701211588576C-1186871050966 50652301427881642C-119856223422353026131301639830122H-0032 4582124139756585602610114051H210673045932913893117802541663 998H-213813960732874026411401597471301C-249727864710282525 530801294381916C-43082143342-1053611479706185877439C-47653 447646-0018147104-04572373726C25328602328037000465620011986 0558C42526672755-1066293316-07393976046C4792766099-0003297 853602708219952N352745873560614022642107654113582N29359790 615-04718493566-10302397411N-29700131679-051219264851000265 899N-3445296333704795753865-08845458663O-24052934908-09382 69441920615506892O-3296372015912888743779-1820167623O35702 8387851388124585917770736126O21895981333-08589762166-194668 78098C-554563937871170668715301219104764H-5667351813119186 353521-0652748806H-652943631230865024603104582287233H-5025 0115681162745189680956029101C-55269548345-05990013826-16446 988455H-64655016676-10299218298-13106051795H-5750182361701 910945586-23506888068H-49590757402-13592994529-21626256034C -51903164113-113883584818593840361H-61878997671-14605946059 1575108602H-47708979411-1859625198825454665015H-52611602265 -019297968422377878049C-40549841819-246242649400686611793H -35451914555-3039510795508287798648H-49911098174-2953439681 6-01720727042H-34341347503-24437308756-08196945991C5577165 9718-0561180303814535013895H64704426185-1064267753410952465 01H586777018760252842931521009316133H49942750613-125732916 6720403510201C5584157596511383272645-03795230303H573253096 011913751293803596650671H6551894131107887504724-07210183978 H5053198920115676057384-1221845751C40181220121-24504821351 -01178614425H34767507793-30647215134-08281748445H495876859 31-2939521707601076580848H34357105039-239279558780793924586 3C50619442421-12187603138-20241509151H60592293407-15798214 694-17936782888H45807562039-19425801596-26696248847H514515 08686-02889110732-25692201428C00034208429-12554978842012109 68413H-06629345204-1607073382208972500018H-03247652174-163 20629061-08424643213H09851125889-1660783623303139701058Vers ion=IA32L-G03RevC02State=3-AHF=-13299426217RMSD=2502e-06RMSF=4 906e-05Dipole=-05071164-08150014-13763423PG=C01 [X(C21H30N4O4)] Job cpu time 8 days 2 hours 54 minutes 74 seconds File lengths (MBytes) RWF= 366 Int= 0 D2E= 0 Chk= 41 Scr= 1 Normal termination of Gaussian 03 at Thu Jul 3 143228 2008

26) Molecule b9

11GINC-PAULINGFOptROHF6-311G(dp)C21H30N4O4(3)SND06-May-20120 P OPT ROHF6-311G(DP) GEOM=CONNECTIVITY SCF=(CONVER=5MAXCYCLE=800 )Optimization03C-0127836679131767906921-04126761742C111 20939625531312808-03672620369C1131272870611690193313-017409 77346C-0048336754604518981997-00559322593C-128081047011090 4933845-01031837975C-1307037373924717924662-02894826349H-0 17255534554240120273-05623024812H-224927944822973861159-035 7861927C-253561283650335307166100164103765C-39645981781-15 27632266603218998966C-47726783303-0244556209-00345739187C2 394327901904120300268-00834201049C38304696156-14427723471-0 3523236452C44985655818-0319133156905018810026N334358291010 596158440407411328509N27015336212-06769675423-09109407357N- 26696366017-0908102874506549596158N-3680511631206947972815- 04160883708O-17515037828-1527048841112199183922O-3989253284 17711796891-10313753515O343371005861487943145916480636946O 19179421385-11437992763-17591344218C-5486703545104042372159 11579009871H-58236523651138739611570857759387H-63462877745 -0184324398414582303684H-482648175760516555419620104400702 C-57462990629-03903731858-11989968508H-64980613085-11345068 185-09527071566H-623424622205562990101-13765794026H-524982 34618-06826294036-21136741537C-44954675678-2326378400615082 103989H-54877385074-2704141857212831796676H-38461334076-31 71631593216965343056H-45447181734-1734757121924116593795C-3 7324142227-24677913932-08697532051H-30179083668-32288768515 -05783041197H-46525668738-2958851014-11643667612H-333290154 09-19404204212-17282049733C50699582437-07714437674184118140 95H58573539114-1500256973316728332036H54852230545008105648 8523578845838H43166514228-1209676527524805668292C554645014 5605076772252-02528679565H578327552891381550913703396074233 H64530693796-00675754537-04029895771H518151612060838275772 8-12185154612C32441282269-25889932672048441034H2650305936 -32241841128-01622470772H40298260152-3191055076309256672163 H26040515918-2222910388312789988579C46938661825-20159821009 -14717719325H55636254041-25126353979-10534606589H412238896 59-2747539171-20290403313H50265813205-12544886469-216332710 14H00003040026-0606685058900813178518C23735792648335557054 64-05485380895H299115358333280929921903378984939H294583224 6629815823913-13934895608H2137755104643947753014-0740813346 8Version=IA64L-G03RevC02State=3-AHF=-13299517299RMSD=4131e-06 RMSF=5546e-05Dipole=02676292-19582718-01475255PG=C01 [X(C21H30 N4O4)]

Job cpu time 1 days 22 hours 56 minutes 164 seconds File lengths (MBytes) RWF= 361 Int= 0 D2E= 0 Chk= 43 Scr= 1 Normal termination of Gaussian 03 at Sun May 6 132717 2012

27) Molecule c9

11GINC-COMPUTE-0-101FOptROHF6-311G(dp)C21H30N4O4(3)SNDUTTA12- Apr-20120p opt rohf6-311g(dp) geom=connectivity scf=(conver=5ma xcycle=800)Optimization03C-0002337013632982418291000215626 27C11916792312259376281590011315932C1199963027412020045339 -00090969557C-000097334505033263497-00066983568C-120086817 19120003558870001439355C-1194127444925941190864-00087023222 H-2129605852731142564463-00385532345C-24833310089047895917 0500021564673C-39710431765-1357307895701084250748C-4725304 577-0032284986-0214523295C2482780422704816301115-0004852327 2C39711485426-13539451276-01106855008C47230928305-00306954 62102250744084N358538714620898567761204800264566N268842840 41-07884411837-05642927448N-26850933115-0794367262055599451 93N-3589413035708982519151-04727646847O-18192762295-146327 3947311465529204O-3832303841620183602007-10374076364O38241 1313482015925974310520647782O18266139178-14535565135-116495 31168C-549289479640562766446309725903089H-5787347993715714 49603607153336999H-63829834006-0018530311211855490543H-488 19566601060423553418672696961C-56305266768-00797167797-1440 5083505H-64139519345-08157035313-12851956898H-608330837808 894818807-15874351217H-50873587328-03303133104-23409139404C -45925311968-2211962497512085342691H-55777564034-25481952434 09014915491H-39760052195-308453358513820970769H-4683051856 -1675466405421427223845C-36891463535-22288946981-1123909891 7H-30103561348-30245708216-08394705047H-46008030608-267684 67011-15020194925H-32269440749-16608512358-19229158102C561 91537347-008491067614574960381H64037653274-0820010988613039 924538H607077164310883478986916131339619H50692799998-03404 83963923524238268C549953494205707039559-09530353346H579214 063815779470988-06881345326H63911294109-00095451075-1162524 6818H4895279655406171040938-18520070159C36804379392-223241 2747511147002449H30037054266-30264554687082095147H45893504 819-2682511041114968494048H32124873288-16688372224191352802 05C46005426463-22024308703-1211071034H55834492119-25405822 08-08987522626H39851777959-30738908761-13940760525H4697963 0484-16606613179-21415120414H-00001422956-05626037632-00078 538135H212636380663115089234500520262219C00035375457480930 92366-00167768869H080254204795202038821206024125478H015151 902651822721359-10267449086H-093610288685207715198034771428 66Version=EM64L-G09RevA02State=3-AHF=-13299538915RMSD=2226e-06 RMSF=1006e-05Dipole=00107637-19650343-00084192Quadrupole=168 567585-60818049-10774953601040436-844849-00971781PG=C01 [X( C21H30N4O4)]

2 Tables of computed total energies and ltS2gt values with B3LYP B3LYP-D3 and M062X6-311+G(dp) scheme

Table S1 Calculated energies and ltS2gt at UB3LYP6-311+G(dp) level

Energy (ltS2gt) in auDiradical BS T

Unsubstituted 12990088363 (1071622) 12990089470 (2078245)

1a 14876244856 (1069849) 14876245171 (2071647)1b 14876305535 (1067333) 14876306235 (2071524)1c 14876408588 (1072854) 14876409655 (2079275)

2a 13982617203 (1065728) 13982617628 (2068029)2b 13982689499 (1067319) 13982690090 (2070472)2c 13982726325 (1067716) 13982727328 (2073899)

3a 17586099274 (1065228) 17586099163 (2064827)3b 17586214600 (1067609) 17586215026 (2069908)3c 17586299757 (1072765) 17586300901 (2079655)

4a 15035457952 (1067558) 15035458232 (2069246)4b 15035547180 (1069430) 15035547727 (2072831)4c 15035618910 (1067875) 15035619953 (2074062)

5a 38725292505 (1065280) 38725292597 (2065815)5b 38725408876 (1067943) 38725409257 (2070078)5c 38725463222 (1067435) 38725464279 (2073677)

6a 13742566758 (1055040) 13742566929 (2056045)6b 13742596085 (1070370) 13742596923 (2074748)6c 13742512027 (1068554) 13742512938 (2073675)

7a 13543616717 (1060900) 13543616896 (2061982)7b 13543859776 (1069196) 13543860486 (2072881)7c 13543808127 (1068317) 13543809016 (2073098)

8a 15301218168 (1094037) 15301218043 (2093781)8b 15301108993 (1065886) 15301109079 (2066589)8c 15301175477 (1007154) 15301176373 (2076571)

9a 13383249780 (1066284) 13383250003 (2067560)9b 13383337335 (1068054) 13383337837 (2070916)9c 13383364092 (1071185) 13383365175 (2077465)

Table S2 Calculated exchange coupling constant (J) at UB3LYP-D36-311+G(dp) level from ROHF6-311G(dp) level triplet optimized geometry

Energy (ltS2gt) in auDiradical T BS

Unsubstituted 12991042382078164

12991041271071481

1a 14877310813207163

148773105071069849

1b 148773346492071572

148773339481067333

1c 14877408129207929

14877407063 1072855

2a 139835797922068025

139835793671065728

2b 139836473632070586

13983646771067277

2c 1398368722073898

139836861431067646

3a 175870686592064841

175870687701065188

3b 175871872932070012

175871868661067575

3c 175872669752079686

17587265831 1072764

4a 150364971322069245

150364968521067558

4b 15036560392072808

15036559843106943

4c 150366084792074044

15036607436 1067875

5a 387262934962065826

38726293404106528

5b 387263951872070104

387263948051067951

5c 387264401642073686

387264391071067413

6a 137435415512056073

137435413821055212

6b 137435763012074834

137435754621070382

6c 1374 348469207369

137434837781068606

7a 13544636592061982

135446364110609

7b 135448593512072894

135448586411069196

7c 13544796562073112

135447956711068314

8a 153022081852061268

153022082541061453

8b 15302235056 15302234969

2066726 10662798c 15302267097

207659315302266201

10715939a 1338429467

206759113384294446

10662859b 13384356259

207092913384355757

10680559c 13384362557

207756813384361474

1071112

Table S3 Calculated energies and ltS2gt at UM062X6-311+G(dp) level from ROHF6-311G(dp) level triplet optimized geometry

Unsubstituted 12984686416 (1119801) 12984687915 (212770)

1a 14870330640 (1116265) 14870331022 (2118370)1b 14870340057 (1110880) 14870340999 (2116127)1c 14870397865 (1122770) 14870399332 (2130684)

2a 13976967708 (1109001) 13976968272 (2111834)2b 13977028581 (1112121) 13977029395 (2116272)2c 13977063573 (1112239) 13977064997 (211992)

3a 17580502560 (1109496) 17580502384 (2108947)3b 17580613859 (1111595) 17580614407 (2114445)3c 17580678866 (1122594) 17580680396 (2130806)

4a 15029423194 (1112089) 15029423540 (2113938)4b 15029471958 (1115222) 15029472702 (2119480)4c 15029509372 (1112737) 15029510816 (2120667)

5a 38720240696 (1108754) 387202407990 (210928)5b 38720329696 (1113565) 38720330178 (2116038)5c 38720365198 (1111698) 38720366626 (2119400)

6a 13736957536 (1087089) 13736957741 (2088132)6b 13736979294 (1119286) 13736980533 (2125335)6c 13736887925 (1114420) 13736889129 (2120742)

7a 1353802557 (1101581) 13538025814 (2102793)7b 13538261238 (1115886) 13538262288 (2121112)7c 13538199461 (1113586) 13538200631 (2119642)

8a 15294780725 (1100643) 15294780616 (2099871)8b 15294801619 (1108433) 15294801712 (2108881)8c 15294830247 (1120630) 15294831442 (2126481)

9a 13377702797 (1111062) 13377703076 (2112311)9b 13377753121 (1113933) 13377753786 (2117188)9c 13377755509 (1118874) 13377756961 (2126541)

3 G03 full reference (43)

Frisch M J Trucks G W Schlegel H B Scuseria G E Robb M A Cheeseman J R Montgomery Jr J A Vreven T Kudin K N Burant J C Millam J M Iyengar S S Tomasi J Barone V Mennucci B Cossi M Scalmani G Rega N Petersson G A Nakatsuji H Hada M Ehara M Toyota K Fukuda R Hasegawa J Ishida M Nakajima T Honda Y Kitao O Nakai H Klene M Li X Knox J E Hratchian H P Cross J B Bakken V Adamo C Jaramillo J Gomperts R Stratmann R E

Yazyev O Austin A J Cammi R Pomelli C Ochterski J W Ayala P Y Morokuma K Voth G A Salvador P Dannenberg J J Zakrzewski V G Dapprich S Daniels A D Strain M C Farkas O Malick D K Rabuck A D Raghavachari K Foresman J B Ortiz J V Cui Q Baboul A G Clifford S Cioslowski J Stefanov B B Liu G Liashenko A Piskorz P Komaromi I Martin R L Fox D J Keith T Al-Laham M A Peng C Y Nanayakkara A Challacombe M Gill P M W Johnson B Chen W Wong M W Gonzalez C and Pople J A Gaussian 03 Revision C02 Gaussian Inc Wallingford CT 2004

Gaussian 09 Revision A1 Frisch M J Trucks G W Schlegel H B Scuseria G E Robb M A Cheeseman J R Scalmani G Barone V Mennucci B Petersson G A Nakatsuji H Caricato M Li X Hratchian H P Izmaylov A F Bloino J Zheng G Sonnenberg J L Hada M Ehara M Toyota K Fukuda R Hasegawa J Ishida M Nakajima T Honda Y Kitao O Nakai H Vreven T Montgomery Jr J A Peralta J E Ogliaro F Bearpark M Heyd J J Brothers E Kudin K N Staroverov V N Kobayashi R Normand J Raghavachari K Rendell A Burant J C Iyengar S S Tomasi J Cossi M Rega N Millam N J Klene M Knox J E Cross J B Bakken V Adamo C Jaramillo J Gomperts R Stratmann R E Yazyev O Austin A J Cammi R Pomelli C Ochterski J W Martin R L Morokuma K Zakrzewski V G Voth G A Salvador P Dannenberg J J Dapprich S Daniels A D Farkas Ouml Foresman J B Ortiz J V Cioslowski J Fox D J Gaussian Inc Wallingford CT 2009

(a) (b)

Fig S1 Calculated J (B3LYP) versus χp the factor of planarity (a) Common ortho J (cmndash1) = ndash270+2061χp (RMSD = 10742) (b) Ortho-para J (cmndash1) = ndash008+2324χp (RMSD = 106) (c) Common meta J (cmndash1) = ndash1245+4544χp (RMSD = 065)

Fig S2 Plot of calculated J (B3LYP) for Type (c) species (common-meta substitution) versus σm J (cmndash1) = 4068σm + 2122 (RMSD = 0322)