Syntheses and coordination chemistry of perfluoroaryl-1H-tetrazoles

Harald Gerhards,a Alexander Krest,a Patrick J. Eulgem,a Dieter Naumann,a Dennis Rokitta,b

Martin Valldor,c Axel Kleina,*

* to whom correspondence should be addressed. Email: axel.klein@uni-koeln.de; Internet: http://www.klein.uni-koeln.de

Supplementary Data

Supplementary Figures (Figures S1–S12)

Figure S1. Crystal structure of BTFTH, viewed along the a axis.

Figure S2. -stacking of BTFTH molecules in the unit cell.

Figure S3. Crystal structure of [(BTFT)2Cu(Py)2]n, viewed along the c axis.

Figure S4. ESI-MS of F5PhTetH, neg. ionisation.

Figure S5. ESI-MS of p-N3F4PhTetH, neg. ionisation.

Figure S6. ESI-MS of F4PyTetH, neg. ionisation.

Figure S7. ESI-MS of 3,5-BTFTH, neg. ionisation.

Figure S8. ESI-MS of 1,2-bis(1H-tetrazol-5-yl)benzene, neg. ionisation.

Figure S9. ESI-MS of 5-amino-1H-tetrazole, neg. ionisation.

Figure S10. ESI-MS of 5-trifluoromethyl-1H-tetrazole, neg. ionisation.

Figure S11. UV/vis absorption spectrum of [(BTFT)2Cu(Py)2]n in the solid.

Figure S12. UV/vis absorption spectra of [(BTFT)2Cu(Py)2]n in DMSO and pyridine.

Supplementary Tables (Tables S1–S10)

Table S1. Full crystal data and structure refinement for BTFTH.

Table S2. Atomic coordinates (x 104) and equivalent isotropic displacement parameters (Å2 x 103) for

BTFTH. U(eq) is defined as one third of the trace of the orthogonalised Uij tensor.Table S3. Bond lengths [Å] and angles [°] for BTFTH.

Table S4. Anisotropic displacement parameters (Å2 x 103) for BTFTH. The anisotropic displacement

factor exponent takes the form: –2π2[ h2a*2U11 + ... + 2 h k a* b* U12].

Table S5. Hydrogen coordinates (x 104) and isotropic displacement parameters (Å2 x 103) for BTFTH.

Table S6. Full crystal data and structure refinement for [(BTFT)2Cu(Py)2]n.

Table S7. Atomic coordinates (x 104) and equivalent isotropic displacement parameters (Å2 x 103) for

[(BTFT)2Cu(Py)2]n. U(eq) is defined as one third of the trace of the orthogonalised Uij tensor.Table S8. Bond lengths [Å] and angles [°] for [(BTFT)2Cu(Py)2]n.

Table S9. Anisotropic displacement parameters (Å2 x 103) for [(BTFT)2Cu(Py)2]n. The anisotropic

displacement factor exponent takes the form: –2π2[ h2a*2U11 + ... + 2 h k a* b* U12].

Table S10. Hydrogen coordinates (x 104) and isotropic displacement parameters (Å2 x 103) for

[(BTFT)2Cu(Py)2]n.

1

Figure S1. Crystal structure of BTFTH, viewed along the a axis. Protons were omitted for clarity.

Figure S2. -stacking of BTFTH molecules in the unit cell. Protons were omitted for clarity.

Figure S3. Crystal structure of [(BTFT)2Cu(Py)2]n, viewed along the c axis.

2

Figure S4. ESI-MS of F5PhTetH, neg. ionisation.

Figure S5. ESI-MS of F4N3PhTetH, neg. ionisation.

3

Figure S6. ESI-MS of F4PyTetH, neg. ionisation.

Figure S7. ESI-MS of 3,5-BTFTH, neg. ionisation.

4

Figure S8. ESI-MS of 1,2-bis(tetrazol-5-yl)benzene, neg. ionisation.

Figure S9. ESI-MS of 5-amino-1H-tetrazole, neg. ionisation.

Figure S10. ESI-MS of 5-trifluoromethyl-1H-tetrazole, neg. ionization.

5

Figure S11. UV/vis absorption spectrum of [(BTFT)2Cu(Py)2]n in a KBr pellet.

Figure S12. UV/vis absorption spectra of [(BTFT)2Cu(Py)2]n dissolved in DMSO (left) and pyridine (right).

Table S1. Full crystal data and structure refinement for BTFTH._____________________________________________________________________________CCDC No. 1409668Empirical formula C9 H4 F6 N4Formula weight 282.10Temperature 293(2) KWavelength 0.71073 ÅCrystal system MonoclinicSpace group P21/nUnit cell dimensions a = 7.3110(10) Å = 90°.

b = 6.743(2) Å = 95.695(18)°.c = 22.090(4) Å = 90°.

Volume 1083.6(4) Å3

Z 4Density (calculated) 1.723 Mg/m3

Absorption coefficient 0.182 mm-1

F(000) 556Crystal size/colour/shape 0.5 x 0.1 x 0.1 mm3/colourless/needleTheta range for data collection 2.861 to 28.195°.Index ranges -9<=h<=9, -8<=k<=8, -29<=l<=29Reflections collected 12561Independent reflections 2520 [R(int) = 0.1802]

6

Completeness to theta = 25.000° 96.3 % Refinement method Full-matrix least-squares on F2

Data / restraints / parameters 2520 / 60 / 168Goodness-of-fit on F2 1.077Final R indices [I>2sigma(I)] R1 = 0.1375, wR2 = 0.3743R indices (all data) R1 = 0.2675, wR2 = 0.4349Extinction coefficient 0.011(11)Largest diff. peak and hole 0.791 and -0.413 e.Å-3

________________________________________________________________________________

Table S2. Atomic coordinates (x 104) and equivalent isotropic displacement parameters (Å2 x 103) for BTFTH. U(eq) is defined as one third of the trace of the orthogonalised Uij tensor.

________________________________________________________________________________x y z U(eq)

________________________________________________________________________________N(5) 1399(9) 1462(10) 10027(3) 64(2)N(2) 3534(10) 3629(10) 10023(3) 69(2)C(16) 2845(11) -801(11) 9014(3) 58(2)C(11) 3701(10) 896(10) 9275(3) 52(2)C(1) 2894(10) 1934(11) 9766(3) 54(2)C(15) 3600(12) -1753(11) 8542(4) 63(2)N(3) 2404(11) 4130(11) 10445(3) 80(2)C(14) 5210(12) -1066(13) 8336(4) 67(2)C(13) 6048(11) 606(13) 8599(3) 62(2)N(4) 1113(10) 2871(11) 10443(3) 77(2)C(12) 5299(11) 1551(13) 9062(3) 65(2)C(25) 2667(13) -3507(14) 8262(4) 80(3)C(23) 7744(13) 1400(13) 8364(4) 83(3)F(1A) 8121(17) 783(18) 7833(5) 109(4)F(2A) 7514(14) 3437(14) 8231(5) 91(3)F(4A) 3860(16) -4811(18) 8058(6) 119(5)F(5A) 1409(19) -3180(20) 7825(6) 140(5)F(6A) 1894(16) -4693(15) 8669(4) 94(4)F(3A) 9160(18) 1340(20) 8764(5) 116(5)F(1B) 8741(17) -179(15) 8162(5) 88(4)F(2B) 7470(20) 2560(20) 7922(6) 118(5)F(4B) 2996(19) -3790(20) 7680(5) 104(5)F(5B) 818(16) -3340(20) 8182(6) 107(5)F(6B) 3050(30) -5110(20) 8555(7) 152(7)F(3B) 8930(16) 2130(20) 8801(4) 77(4)_____________________________________________________________________________

Table S3. Bond lengths [Å] and angles [°] for BTFTH.N(5)-C(1) C(1)-N(5)-N(4) 108.5(6) F(5A)-C(25)-

C(15)116.3(10)

N(5)-N(4) C(1)-N(2)-N(3) 107.2(6) F(4B)-C(25)-C(15)

113.5(9)

N(2)-C(1) C(15)-C(16)-C(11)

119.6(7) F(4A)-C(25)-C(15)

112.1(10)

N(2)-N(3) C(12)-C(11)-C(16)

118.8(7) F(5B)-C(25)-C(15)

113.9(9)

C(16)-C(15)

1 C(12)-C(11)-C(1)

121.3(7) F(6A)-C(25)-C(15)

113.4(8)

C(16)-C(11)

1 C(16)-C(11)-C(1)

120.0(6) F(3A)-C(23)-F(1A)

112.3(9)

C(11)-C(12)

1 N(5)-C(1)-N(2) 106.7(6) F(2B)-C(23)-F(3B)

112.1(10)

C(11)-C(1)

1 N(5)-C(1)-C(11) 128.2(7) F(2B)-C(23)-F(1B)

106.1(9)

C(15)-C(14)

1 N(2)-C(1)-C(11) 125.0(6) F(3B)-C(23)-F(1B)

101.2(9)

7

C(15)-C(25)

1 C(14)-C(15)-C(16)

120.6(8) F(3A)-C(23)-F(2A)

104.2(9)

N(3)-N(4) C(14)-C(15)-C(25)

120.3(7) F(1A)-C(23)-F(2A)

99.0(8)

C(14)-C(13)

1 C(16)-C(15)-C(25)

119.1(7) F(2B)-C(23)-C(13)

114.9(11)

C(13)-C(12)

1 N(4)-N(3)-N(2) 109.6(6) F(3A)-C(23)-C(13)

112.9(10)

C(13)-C(23)

1 C(13)-C(14)-C(15)

119.3(7) F(1A)-C(23)-C(13)

117.2(9)

C(25)-F(6B)

1 C(12)-C(13)-C(14)

120.1(7) F(3B)-C(23)-C(13)

112.8(8)

C(25)-F(5A)

1 C(12)-C(13)-C(23)

120.2(8) F(1B)-C(23)-C(13)

108.5(9)

C(25)-F(4B)

1 C(14)-C(13)-C(23)

119.7(7) F(2A)-C(23)-C(13)

109.6(7)

C(25)-F(4A)

1 N(3)-N(4)-N(5) 107.9(6)

C(25)-F(5B)

1 C(13)-C(12)-C(11)

121.6(8)

C(25)-F(6A)

1 F(6B)-C(25)-F(4B)

108.2(10)

C(23)-F(2B)

1 F(5A)-C(25)-F(4A)

107.6(10)

C(23)-F(3A)

1 F(6B)-C(25)-F(5B)

107.4(11)

C(23)-F(1A)

1 F(4B)-C(25)-F(5B)

99.2(9)

C(23)-F(3B)

1 F(5A)-C(25)-F(6A)

106.5(10)

C(23)-F(1B)

1 F(4A)-C(25)-F(6A)

99.3(8)

C(23)-F(2A)

1 F(6B)-C(25)-C(15)

113.5(12)

Table S4. Anisotropic displacement parameters (Å2 x 103) for BTFTH. The anisotropic displacement factor exponent takes the form: –2π2[ h2a*2U11 + ... + 2 h k a* b* U12].

______________________________________________________________________________U11 U22 U33 U23 U13 U12

______________________________________________________________________________N(5) 62(4) 70(4) 62(4) -13(3) 21(3) -18(3)N(2) 72(5) 68(5) 69(4) -10(3) 19(4) -17(4)C(16) 58(5) 50(4) 67(5) -2(4) 9(4) -6(4)C(11) 54(5) 47(4) 56(4) 0(3) 11(4) -9(3)C(1) 47(4) 62(5) 52(4) -1(3) 7(3) -10(4)C(15) 67(5) 53(5) 69(5) -8(4) 11(4) 0(4)N(3) 77(5) 79(5) 88(5) -24(4) 30(4) -25(4)C(14) 65(6) 80(6) 58(4) -8(4) 10(4) 14(4)C(13) 48(5) 79(5) 59(4) -3(4) 16(4) -7(4)N(4) 67(5) 86(5) 80(4) -23(4) 23(4) -22(4)C(12) 57(5) 76(6) 64(5) 1(4) 10(4) -10(4)C(25) 83(7) 78(6) 82(6) -6(5) 21(5) 12(5)C(23) 69(7) 112(8) 67(5) -22(5) 10(5) 7(5)_____________________________________________________________________________

Table S5. Hydrogen coordinates (x 104) and isotropic displacement parameters (Å2 x 103) for BTFTH.________________________________________________________________________________

x y z U(eq)________________________________________________________________________________H(16) 1777 -1285 9157 70H(14) 5724 -1722 8023 81

8

H(12) 5885 2664 9239 79_____________________________________________________________________________

Table S6. Full crystal data and structure refinement for [(BTFT)2Cu(Py)2]n._____________________________________________________________________________CCDC No. 1052484Empirical formula C28 H16 Cu F12 N10Formula weight 784.05Temperature 293(2) KWavelength 0.71073 ÅCrystal system OrthorhombicSpace group PccaUnit cell dimensions a = 35.2362(13) Å = 90°.

b = 11.5212(3) Å = 90°.c = 7.3291(2) Å = 90°.

Volume 2975.35(16) Å3

Z 4Density (calculated) 1.750 Mg/m3

Absorption coefficient 0.850 mm-1

F(000) 1564Crystal size/colour/shape 0.4 x 0.1 x 0.1 mm3/blue/needleTheta range for data collection 1.77 to 26.84°.Index ranges -44<=h<=44, -14<=k<=14, -8<=l<=9Reflections collected 45686Independent reflections 3179 [R(int) = 0.0981]Completeness to theta = 26.84° 99.1 % Refinement method Full-matrix least-squares on F2

Data / restraints / parameters 3179 / 0 / 232Goodness-of-fit on F2 1.043Final R indices [I>2sigma(I)] R1 = 0.0644, wR2 = 0.1867R indices (all data) R1 = 0.0933, wR2 = 0.2149Extinction coefficient 0.0021(9)Largest diff. peak and hole 1.248 and -0.547 e.Å-3

________________________________________________________________________________

Table S7. Atomic coordinates (x 104) and equivalent isotropic displacement parameters (Å2 x 103) for [(BTFT)2Cu(Py)2]n. U(eq) is defined as one third of the trace of the orthogonalised Uij tensor.

________________________________________________________________________________x y z U(eq)

________________________________________________________________________________Cu(1) 0 3859(1) 2500 51(1)F(17B) 1738(2) 6326(5) -2678(5) 128(2)F(17C) 2009(1) 5081(4) -1083(7) 124(2)F(17A) 2279(1) 6715(5) -1525(7) 137(2)F(16C) 1675(1) 9706(5) 4552(13) 217(4)F(16B) 2069(3) 8564(4) 5459(10) 212(4)F(16A) 2174(2) 9455(6) 3327(11) 195(3)N(4) 300(1) 6017(3) 4175(5) 49(1)N(2) 713(1) 5175(3) 2365(5) 47(1)N(3) 373(1) 5089(3) 3169(5) 48(1)N(5) 594(1) 6732(3) 4036(5) 50(1)N(20) -343(1) 2580(3) 1449(5) 49(1)C(10) 1213(1) 6665(4) 2431(5) 48(1)C(1) 841(1) 6194(3) 2941(6) 45(1)C(14) 1758(1) 6696(4) 479(7) 62(1)C(24) -935(1) 1593(4) 1229(7) 61(1)C(11) 1371(1) 7552(4) 3450(6) 53(1)C(15) 1407(1) 6228(4) 952(6) 57(1)C(25) -709(1) 2471(4) 1907(6) 53(1)C(13) 1920(1) 7581(4) 1492(8) 66(1)

9

C(12) 1722(1) 8007(4) 2973(7) 62(1)C(23) -783(2) 820(4) 25(8) 70(1)C(21) -199(1) 1819(4) 257(7) 63(1)C(22) -406(2) 942(4) -488(8) 75(1)C(16) 1892(2) 8922(5) 4140(10) 78(2)C(17) 1953(2) 6217(6) -1190(10) 85(2)________________________________________________________________________________

Table S8. Bond lengths [Å] and angles [°] for [(BTFT)2Cu(Py)2]n.Cu(1)-N(3) 1

.995(3)N(3)-Cu(1)-N(3)#1 8

9.44(19)C(11)-C(10)-C(1)

119.8(4)

Cu(1)-N(3)#1 1.995(3)

N(3)-Cu(1)-N(20)#1

91.72(14)

N(2)-C(1)-N(5) 112.3(3)

Cu(1)-N(20)#1

2.055(3)

N(3)#1-Cu(1)-N(20)#1

171.53(14)

N(2)-C(1)-C(10) 123.4(4)

Cu(1)-N(20) 2.055(3)

N(3)-Cu(1)-N(20) 171.53(14)

N(5)-C(1)-C(10) 124.3(4)

F(17B)-C(17) 1.335(9)

N(3)#1-Cu(1)-N(20)

91.72(14)

C(13)-C(14)-C(15)

121.0(5)

F(17C)-C(17) 1.325(7)

N(20)#1-Cu(1)-N(20)

88.37(18)

C(13)-C(14)-C(17)

121.3(4)

F(17A)-C(17) 1.309(7)

N(3)-N(4)-N(5) 107.9(3) C(15)-C(14)-C(17)

117.7(5)

F(16C)-C(16) 1.221(7)

C(1)-N(2)-N(3) 103.3(3) C(23)-C(24)-C(25)

119.0(4)

F(16B)-C(16) 1.223(8)

N(4)-N(3)-N(2) 111.0(3) C(23)-C(24)-H(24)

120.5

F(16A)-C(16) 1.310(8)

N(4)-N(3)-Cu(1) 125.7(2) C(25)-C(24)-H(24)

120.5

N(4)-N(3) 1.324(5)

N(2)-N(3)-Cu(1) 122.3(3) C(10)-C(11)-C(12)

120.2(4)

N(4)-N(5) 1.326(4)

N(4)-N(5)-C(1) 105.4(3) C(10)-C(11)-H(11)

119.9

N(2)-C(1) 1.327(5)

C(21)-N(20)-C(25) 117.9(4) C(12)-C(11)-H(11)

119.9

N(2)-N(3) 1.339(4)

C(21)-N(20)-Cu(1) 119.4(3) C(10)-C(15)-C(14)

119.8(4)

N(5)-C(1) 1.337(5)

C(25)-N(20)-Cu(1) 122.6(3) C(10)-C(15)-H(15)

120.1

N(20)-C(21) 1.337(6)

C(15)-C(10)-C(11) 119.6(4) C(14)-C(15)-H(15)

120.1

N(20)-C(25) 1.338(5)

C(15)-C(10)-C(1) 120.6(4) N(20)-C(25)-C(24)

122.3(4)

C(10)-C(15) 1.377(6)

C(11)-C(10)-C(1) 119.8(4) N(20)-C(25)-H(25)

118.8

C(10)-C(11) 1.384(6)

N(2)-C(1)-N(5) 112.3(3) C(24)-C(25)-H(25)

118.8

C(10)-C(1) 1.465(5)

N(2)-C(1)-C(10) 123.4(4) C(12)-C(13)-C(14)

118.6(4)

C(14)-C(13) 1.383(7)

N(5)-C(1)-C(10) 124.3(4) C(12)-C(13)-H(13)

120.7

C(14)-C(15) 1.395(6)

C(13)-C(14)-C(15) 121.0(5) C(14)-C(13)-H(13)

120.7

C(14)-C(17) 1.507(8)

C(13)-C(14)-C(17) 121.3(4) C(13)-C(12)-C(11)

120.9(4)

C(24)-C(23) 1.362(7)

C(15)-C(14)-C(17) 117.7(5) C(13)-C(12)-C(16)

120.2(5)

C(24)-C(25) 1.381(6)

C(23)-C(24)-C(25) 119.0(4) C(11)-C(12)-C(16)

118.8(5)

C(24)-H(24) 0.9300 C(23)-C(24)-H(24) 120.5 C(24)-C(23)-C(22)

119.0(4)

10

C(11)-C(12) 1.388(6)

C(25)-C(24)-H(24) 120.5 C(24)-C(23)-H(23)

120.5

C(11)-H(11) 0.9300 C(10)-C(11)-C(12) 120.2(4) C(22)-C(23)-H(23)

120.5

C(15)-H(15) 0.9300 C(10)-C(11)-H(11) 119.9 N(20)-C(21)-C(22)

122.9(4)

C(25)-H(25) 0.9300 N(3)-Cu(1)-N(3)#1 89.44(19)

N(20)-C(21)-H(21)

118.5

C(13)-C(12) 1.380(8)

N(3)-Cu(1)-N(20)#1

91.72(14)

C(22)-C(21)-H(21)

118.5

C(13)-H(13) 0.9300 N(3)#1-Cu(1)-N(20)#1

171.53(14)

C(21)-C(22)-C(23)

118.7(5)

C(12)-C(16) 1.484(7)

N(3)-Cu(1)-N(20) 171.53(14)

C(21)-C(22)-H(22)

120.6

C(23)-C(22) 1.387(8)

N(3)#1-Cu(1)-N(20)

91.72(14)

C(23)-C(22)-H(22)

120.6

C(23)-H(23) 0.9300 N(20)#1-Cu(1)-N(20)

88.37(18)

F(16C)-C(16)-F(16B)

112.0(8)

C(21)-C(22) 1.362(7)

N(3)-N(4)-N(5) 107.9(3) F(16C)-C(16)-F(16A)

103.9(6)

C(21)-H(21) 0.9300 C(1)-N(2)-N(3) 103.3(3) F(16B)-C(16)-F(16A)

97.5(7)

C(22)-H(22) 0.9300 N(4)-N(3)-N(2) 111.0(3) F(16C)-C(16)-C(12)

114.5(5)

N(4)-N(3)-Cu(1) 125.7(2) F(16B)-C(16)-C(12)

115.0(5)

N(2)-N(3)-Cu(1) 122.3(3) F(16A)-C(16)-C(12)

112.1(6)

N(4)-N(5)-C(1) 105.4(3) F(17A)-C(17)-F(17C)

108.3(6)

C(21)-N(20)-C(25) 117.9(4) F(17A)-C(17)-F(17B)

107.7(6)

C(21)-N(20)-Cu(1) 119.4(3) F(17C)-C(17)-F(17B)

103.0(6)

C(25)-N(20)-Cu(1) 122.6(3) F(17A)-C(17)-C(14)

113.1(6)

C(15)-C(10)-C(11) 119.6(4) F(17C)-C(17)-C(14)

112.4(5)

C(15)-C(10)-C(1) 120.6(4) F(17B)-C(17)-C(14)

111.7(5)

Symmetry transformations used to generate equivalent atoms: #1 -x,y,-z+1/2

Table S9. Anisotropic displacement parameters (Å2 x 103) for [(BTFT)2Cu(Py)2]n. The anisotropic displacement factor exponent takes the form: –2π2[ h2a*2U11 + ... + 2 h k a* b* U12].

______________________________________________________________________________U11 U22 U33 U23 U13 U12

______________________________________________________________________________Cu(1) 35(1) 39(1) 79(1) 0 -7(1) 0F(17B) 130(4) 178(5) 75(3) -5(3) 18(2) 1(3)F(17C) 132(3) 111(3) 129(4) -14(3) 50(3) 21(3)F(17A) 92(3) 175(4) 145(4) -30(3) 59(3) -49(3)F(16C) 92(3) 156(4) 402(11) -188(6) -70(5) 28(3)F(16B) 330(9) 104(3) 203(6) -26(4) -187(7) -1(5)F(16A) 171(5) 182(6) 233(6) -57(5) 19(5) -126(5)N(4) 44(2) 43(2) 59(2) -3(2) 2(1) -2(1)N(2) 35(1) 47(2) 59(2) -1(2) 1(1) -3(1)N(3) 37(1) 48(2) 60(2) -2(2) 0(1) -2(1)N(5) 45(2) 49(2) 55(2) 0(2) 1(2) -5(1)N(20) 43(2) 43(2) 62(2) 3(2) -2(1) -3(1)C(10) 39(2) 51(2) 54(2) 6(2) -2(2) -5(2)

11

C(1) 40(2) 48(2) 48(2) 2(2) -3(2) -1(2)C(14) 47(2) 69(3) 71(3) 9(2) 4(2) -5(2)C(24) 48(2) 61(2) 73(3) 1(2) -4(2) -11(2)C(11) 47(2) 51(2) 62(3) 2(2) -6(2) -8(2)C(15) 53(2) 59(2) 60(2) 3(2) 2(2) -8(2)C(25) 46(2) 54(2) 58(2) -2(2) -2(2) -4(2)C(13) 45(2) 66(3) 87(4) 14(3) 1(2) -10(2)C(12) 47(2) 59(2) 80(3) 11(2) -9(2) -9(2)C(23) 72(3) 52(2) 85(3) -11(2) -9(3) -13(2)C(21) 58(2) 52(2) 78(3) -4(2) 14(2) -3(2)C(22) 81(3) 58(3) 86(4) -17(3) 6(3) -5(2)C(16) 65(3) 62(3) 107(4) 0(3) -18(3) -15(2)C(17) 65(3) 102(5) 89(4) 10(3) 24(3) -4(3)______________________________________________________________________________

Table S10. Hydrogen coordinates (x 104) and isotropic displacement parameters (Å2 x 103) for [(BTFT)2Cu(Py)2]n.

________________________________________________________________________________x y z U(eq)

________________________________________________________________________________H(24) -1187 1529 1590 73H(11) 1242 7845 4457 64H(15) 1304 5624 271 69H(25) -814 3005 2711 63H(13) 2156 7881 1181 80H(23) -930 221 -446 84H(21) 55 1893 -77 75H(22) -298 435 -1325 90________________________________________________________________________________

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