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Synthesis, Crystal Structure, andCharacterization of A New Adduct Bis-(2-Amino-3-Benzyloxypyridinium) SelenateMonohydrate [C12H13N2O]2SeO4.H2OSami Soukrata a , Mohamed Belhouchet a , Joen Josep Suñol b &Tahar Mhiri aa Laboratoire physico-chimie de l’Etat Solide, Département deChimie, Faculté des Sciences de Sfax , Université de Sfax , 3018 ,Sfax , Tunisiab Departamento De Fisica , Universita de Girona, Compus Montilivi ,Girona , 17071 , SpainAccepted author version posted online: 02 Sep 2013.Publishedonline: 28 Jan 2014.

To cite this article: Sami Soukrata , Mohamed Belhouchet , Joen Josep Suñol & Tahar Mhiri(2014) Synthesis, Crystal Structure, and Characterization of A New Adduct Bis-(2-Amino-3-Benzyloxypyridinium) Selenate Monohydrate [C12H13N2O]2SeO4.H2O, Phosphorus, Sulfur, and Silicon andthe Related Elements, 189:3, 422-431, DOI: 10.1080/10426507.2013.819872

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Phosphorus, Sulfur, and Silicon, 189:422–431, 2014Copyright C© Taylor & Francis Group, LLCISSN: 1042-6507 print / 1563-5325 onlineDOI: 10.1080/10426507.2013.819872

SYNTHESIS, CRYSTAL STRUCTURE, ANDCHARACTERIZATION OF A NEW ADDUCTBIS-(2-AMINO-3-BENZYLOXYPYRIDINIUM) SELENATEMONOHYDRATE [C12H13N2O]2SeO4.H2O

Sami Soukrata,1 Mohamed Belhouchet,1 Joen Josep Sunol,2

and Tahar Mhiri11Laboratoire physico-chimie de l’Etat Solide, Departement de Chimie, Faculte desSciences de Sfax, Universite de Sfax, 3018 Sfax, Tunisia2Departamento De Fisica, Universita de Girona, Compus Montilivi, Girona 17071,Spain

GRAPHICAL ABSTRACT

Abstract A new adduct bis-(2-amino-3-benzyloxypyridinium) selenate monohydrate,[C12H13N2O]2SeO4.H2O, has been synthesized by slow evaporation at room temperatureusing 2-amino-3-benzyloxypyridine as the structure-directing agent. The structure, determinedby single-crystal X-ray diffraction at 298 K, can be described as organic-inorganic tunnelswith different forms built by infinite inorganic chains parallel to the c axis and connected to theorganic cations. In this atomic arrangement, hydrogen bonds and van der Waals interactionsbetween the different species play an important role in the tri-dimensional network cohesion.Solid-state 13C and 77Se MAS NMR spectroscopy results are in agreement with the X-raystructure.

Received 20 April 2013; accepted 24 June 2013.The authors express their most grateful thanks to Xavier Fontrodona, from Compus Montilivi, Universita de

Girona, for the X-ray data collection.Address correspondence to Mohamed Belhouchet, Laboratoire physico-chimie de l’Etat Solide,

Departement de Chimie, Faculte des Sciences de Sfax, Universite de Sfax, 3018 Sfax, Tunisia. E-mail:belhouchet2002@yahoo.fr

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BIS-(2-AMINO-3-BENZYLOXYPYRIDINIUM) SELENATE MONOHYDRATE 423

[Supplementary materials are available for this article. Go to the publisher’s online edition ofPhosphorus, Sulfer, and Silicon and the Related Elements for the following free supplementalfiles: Additional figures and tables.]

Keywords Organic-selenate; crystal structure; hydrogen bonds; infrared, Raman, and NMRspectroscopy

INTRODUCTION

In recent years, studies on the self-assembly of acid-base hydrogen-bond interactionsand molecular recognition in the solid state have shown a great variety of physical andchemical properties in this class of materials. These hybrid crystals are potentially goodmaterials for exhibiting nonlinear optical,1–2 electronic, thermal, and catalytic properties.3–4

The anionic acid part is responsible for favorable chemical and mechanical properties dueto the formation of strongly directional hydrogen bonds, while the organic base is mainlyresponsible for nonlinear optical properties due to its relatively high hyperpolarizability.5–7

We are continuing our studies on the characterization of acid-base hybrid crystals.8–9 Thestructural properties of these hybrid materials are significantly influenced by the nature ofthe organic molecule, such as length, geometry, and the presence of functionalized groups.In this context, the series of organic selenates exhibits rich structural and compositionaldiversity, presenting a particular crystal chemistry with weak and strong hydrogen bonds,as well as van der Waals forces contributing to the cohesion of these compounds. Tobenefit from these materials, a good knowledge of their structural characteristics is fun-damental, not only for the design of other hybrid compounds, but also for the predictionof their physico-chemical properties. Results from X-ray crystallography, NMR, Raman,and IR spectroscopy are combined to provide a description of the new organic selenatemonohydrate, [C12H13N2O]2SeO4.H2O.

RESULTS AND DISCUSSION

Crystal Structure

Structural determination shows that the title compound crystallizes in the Monoclinicspace group C2/c. The asymmetric unit of the title compound is depicted in Figure 1 andconsists of two SeO4

2− anions, two water molecules, and four organic cations, which areconnected through N–H . . . O and O–H . . . O hydrogen bonds building organic-inorganictunnels with different forms (Figure 2).

The selenate anions are inter-connected between themselves by H-bonds involvingH-atoms of water molecules leading to (SeO4.H2O)n

2n− chains parallel to the c axis (seeFigure S1 and Table S1 in online Supplemental Materials). In this atomic arrangement,the SeO4

2− tetrahedra are slightly distorted with Se–O distances ranging from 1.660(2)Å to 1.655(2) Å in Se(1)O4

2− and from 1.623(2) Å to 1.666(2) Å in Se(2)O42−. The

corresponding O–Se–O angle values vary respectively, from 106.67(9)◦ to 111.86(9)◦ andfrom 107.20(1)◦ to 111.28(9)◦ (Table 1). These values are comparable to the reported datain similar compounds.10–13 The differences between the Se-O bonds of the SeO4

2– anionsare well correlated with the number and the strength of the hydrogen bonds formed by theoxygen atoms. The longer bonds (from 1.660(2) Å to 1.667(2) Å) involve oxygen atomsacting as H-acceptors participating in two or three hydrogen bonds of the type N–H . . . Oand O–H . . . O, whereas shorter bonds ranging from 1.623(2) Å to 1.626(2) Å relate the

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424 S. SOUKRATA ET AL.

Figure 1 Asymmetric unit of [C12H13N2O]2SeO4.H2O. H atoms of carbon were omitted for clarity. (Color figureavailable online).

Figure 2 View down the c axis of the atomic arrangement of [C12H13N2O]2SeO4.H2O. (Color figure availableonline).

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BIS-(2-AMINO-3-BENZYLOXYPYRIDINIUM) SELENATE MONOHYDRATE 425

Table 1 Main interatomic distances (Å) and angles (◦) in SeO42− entities

Tetrahedron Se(1)O4

Se1 O11 O12 O13 O14O11 1.655 (2) 107.22 (9) 111.2 (1) 108.7 (1)O12 2.674 (3) 1.667 (2) 111.86 (9) 106.67 (9)O13 2.708 (4) 2.728 (3) 1.626 (2) 110.9 (1)O14 2.695 (3) 2.669 (3) 2.707 (4) 1.660 (2)

Tetrahedron Se(2)O4

Se2 O21 O22 O23 O24O21 1.666 (2) 108.99 (8) 107.60 (9) 111.28 (9)O22 2.699 (3) 1.650 (2) 107.2 (1) 110.5 (1)O23 2.682 (3) 2.662 (3) 1.657 (2) 111.1 (1)O24 2.715 (3) 2.689 (4) 2.705 (4) 1.623 (2)

oxygen atoms acting also as H-acceptors involving only one hydrogen bond and the twooxygen atoms that are not included in the hydrogen bonding scheme.

An examination of the organic moiety geometrical features shows that the dihedralangle between the pyridine ring and benzene plane is 4.8◦, 81.4◦, 48.3◦, and 44.4◦ respec-tively, for cations A, B, C, and D. The main value of the C–C bond lengths in the pyridineand phenyl rings of the four cations is 1.396 Å., which is between a single and double bondand agrees with that in benzene.14 The C–C, C–N bond lengths vary from 1.333(3) Å to1.519(4) Å, the C–C–N, C–C–C angles are included between 116.8(2)◦ and 124.1(2)◦, andC–C–O, C–O–C angles range from 108.6(2)◦ to 127.5(2)◦ (see Table S2 in online Sup-plemental Materials). They are in agreement with those found in related compounds.15–18

The rings of the successive cations are approximately parallel to each other. The centroid-to-centroid distances between adjacent aromatic rings are equal to 3.581 Å and 3.667 Å(Figure 3), which are less 3.8 Å, the maximum value accepted for π–π interactions.19

The organic and inorganic species establish between them two types of hydrogenbonds. The first one is O–H . . . O, involving short contacts with H . . . O lengths rangingbetween 1.91 Å and 2.25 Å, connecting the SeO4

2− and H2O entities to develop the inorganicchains parallel to the c axis. The second type is N–H . . . O, with H . . . O distances rangingfrom 1.85 Å to 2.43 Å, linking the organic cations to the inorganic chains (see Table S1 andFigure S2 in online Supplemental Materials). The pattern of hydrogen bonds contributeswith the electrostatic and van der Waals interactions to the cohesion of the network.

NMR Results

High resolution NMR spectroscopy is a powerful technique for the characterization ofselenates. From the isotropic chemical shift values of NMR components, structural aspectshave been studied. The one isotropic band of the 77Se CP-MAS-NMR of the crystallineselenate monohydrate of bis-(2-amino-3-benzyloxypyridinium) was deconvoluted with aDmfit program.20 After that, two peaks are obtained at 2669.5 and 2596.0 ppm (Figure 4).This confirms that two independent crystallographic sites are occupied by the SeO4 tetra-hedra. The highest signal at 2669.5 ppm can be attributed to the Se(1) and the second signalat 2596.0 to the Se(2), since the oxygen atoms of Se(1) are involved in more hydrogenbonds than the oxygen atoms of Se(2). The experimental chemical shift of the 77Se MASNMR depends on the nature of the tetrahedron.21–22

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Figure 3 π–π interactions between antiparallel cations. (Color figure available online).

Figure 4 77Se MAS-NMR spectrum of [C12H13N2O]2SeO4.H2O. (Color figure available online).

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BIS-(2-AMINO-3-BENZYLOXYPYRIDINIUM) SELENATE MONOHYDRATE 427

Figure 5 13C MAS-NMR spectrum of [C12H13N2O]2SeO4.H2O.

Figure 5 shows the 13C CP-MAS-NMR spectra of the title compound. In these spectra,the presence of a resonance peak number superior to 12 proves the existence of fourcrystallographically independent organic cations in the asymmetric unit of the compoundstructure.23 Thus NMR spectroscopy study confirms the result given by the X-ray data.

To assign NMR components to different carbon atoms, we used Chem-Draw Ultra6.0 calculations. The results obtained and the signal attributions are gathered in Table 2.

Infrared and Raman Spectroscopy

FTIR and Raman spectra of [C12H13N2O]2SeO4.H2O have been recorded at roomtemperature (see Figure 6 and online Figure S3). To assign IR peaks to vibrational modes,we have examined the modes and frequencies in similar compounds.24–26 The assignments

Table 2 Calculated and experimental chemical shifts of the carbon atoms of organic entities

Carbon C8 and C9 andatoms C6 C3 C4 C12 C10 C11 C2 C7 C5 C1

δcal. (ppm) 70.9 113.5 122.3 127.2 127.7 129.0 139.8 141.2 141.6 148.6δexp. (ppm) 73.6 109.4,

113.4,116.7

118.8,121.5,124.2

127.1 128.2 132.7,134.4

142.6 144.3 145.1 149.1

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Figure 6 IR spectrum of [C12H13N2O]2SeO4.H2O.

of the bands observed in the infrared and Raman spectra of [C12H13N2O]2SeO4.H2O arelisted in Table 3.

The isolated SeO42− tetrahedron with an ideal Td symmetry has four vibrational

modes: two stretching modes, ν3 and ν1, and two deformation modes, ν4 and ν2. Thesemodes are observed at 876, 837, 415, and 345 cm−1, respectively.27 Two strong bands at903 and 844 cm−1 are observed in the IR spectrum; in the Raman spectrum, these bandsare shown at 854 and 824 cm−1. The intensities of these bands are strong. These bands areassigned to ν3(SeO4

2−) and ν1(SeO42−) vibrations, respectively. The bending vibrations

arising from the ν4(SeO42−) of the selenate anions are observed as a medium band at

418 cm−1 in IR spectrum only. The bands observed at 355 cm−1 in Raman spectrum areproposed as originating from ν2(SeO4

2−) bending vibrations.The broad bands that appear at 3376, 3284, and 3066 cm−1 are attributed, respectively,

to ν(OH), νas, and νs vibrations of NH associated by hydrogen bonds. The broad bandsobserved between 2700 cm−1 and 1700 cm−1 in IR spectrum can be assigned to the ABCbands of the OH stretching vibrations. The observed bands at 1664, 1570 cm−1 in IR and1605, 1560 cm−1 in Raman are assigned to νas and νs vibrations of NH2, respectively.The strong peak situated at 1496 cm−1 in IR and 1440 cm−1 in Raman is assigned to thedeformation of CH2. The strong peak observed at 1372 cm−1 in IR and 1389 cm−1 inRaman is attributed to the vibration ν(C C). The observed bands at 1284 and 726 cm–1 inIR and 1269 and 742 cm−1 in Raman can be assigned respectively to the modes waggingand rocking of the CH2 group. The observed bands between 1250 cm−1 and 1000 cm−1

corresponds to the stretching vibrations ν(C–N), ν(C–C), δ(C–H), δ(N–H), and δ(O–H).

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BIS-(2-AMINO-3-BENZYLOXYPYRIDINIUM) SELENATE MONOHYDRATE 429

Table 3 Infrared and Raman spectral data (cm−1) and band assignments for [C12H13N2O]2SeO4.H2O sample

IR wavenumbers (cm−1) Raman wavenumbers (cm−1) Assignment

3376 m — ν(OH)3284 m — νs(NH)3066 vw — νas(NH)2700—1700 s — ν(OH) “A + B + C”1664 vs 1605 m δas(NH2)1570 vs 1560 m δs(NH2)1496 s 1440 m δ(CH2)1372 s 1389 s ν(C C)1284 s 1269 w w(CH2)1250 s 1213 m1184 w 1184 w— 1154 w ν(C–N) + ν(C–C) + δ(C–H) +1047 s 1048 w δ(N–H) and δ(OH)1000 vs 1028 w–1002 vs903 s 854 s ν3(SeO4)844 s 824 s ν1(SeO4)726 m 742 w r(CH2)418 m — ν4(SeO4)— 355 w ν2(SeO4)

vs, very strong; s, strong; m, medium; w, weak; vw, very weak.

CONCLUSION

The novel organic selenate template by 2-amino-3-benzyloxypyridinium with thegeneral formula [C12H13N2O]2SeO4.H2O has been synthesized by slow evaporation andcharacterized by single crystal X-ray diffraction, infrared, Raman scattering, 13C, and77Se NMR spectroscopy. Its crystal structure has been described and compared with thoseof other homologous compounds. The results as obtained reveal a new crystal structurearrangement, essentially characterized by the presence of organic-inorganic tunnels. To ourbest knowledge, this kind of atomic arrangement is observed for the first time in this familyof compounds. Most infrared and Raman bands corresponding to vibrational modes wereassigned by comparison with similar compounds. Solid-state MAS NMR is found to givea rather good insight of the chemical shift relative to 13C and 77Se.

EXPERIMENTAL

Synthesis of [C12H13N2O]2SeO4.H2O

The title compound, [C12H13N2O]2SeO4.H2O, was prepared from an aqueous solu-tion (20 mL) containing 2-amino-3-benzyloxy pyridine (99%; 0.8 g, 4 mmol) dissolvedin water and selenic acid H2SeO4 (0.58 g, 5.9 mmol; 99.99%, d = 1.407). This mixturewas stirred for 30 min and then it was slowly evaporated at room temperature for severaldays until the formation of transparent plate single crystals of good quality and suitabledimensions for crystallographic study.

Investigation Techniques

The title compound has been studied by various physico-chemical methods: X-raydiffraction, solid-state NMR, Infrared, and Raman spectroscopy.

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Table 4 Crystal data and experimental parameters used for the intensity data collection, strategy, and final resultsof the structure determination

Empirical formula [C12H13N2O]2SeO4.H2O

Formula weight 563.46Crystal system/Space group Monoclinic/C2/ca/Å 41.23 (4)b/Å 10.39 (1)c/Å 24.81 (3)α/◦ 90β/◦ 92.16 (2)γ /◦ 90V/Å3 10625 (19)Z 16D calc (g/cm3) 1.409μ (mm−1) 1.46Crystal size (mm) 0.3 × 0.2 × 0.1Color/Shape Transparent/BlockTemp (K) 298 (2)Theta range for collection 1.9–28.1Reflections collected 76318Independent reflections 12586Data/restraints/parameters 8865/0/649Goodness of fit on F2 1.02Final R indices [I > 2σ (I)] 0.0375R indices (all data) 0.0952Largest difference peak/hole −0.23/0.46

X-Ray Diffraction

A suitable crystal was carefully selected under a polarizing microscope and mountedat the end of a thin glass fiber. Crystal structure determination was performed using aBRUKER SMART APEX CCD diffractometer that uses graphite monochromatized MoKα

radiation (λ = 0.71073 Å). The unit cell parameters, optimized by least-squares refinement,were calculated and refined using indexation of collected intensities. The total number ofmeasured reflections was 76,318 among which 12,586 were independent and 8,865 hadintensity I > 2σ (I). The structure of the [C12H13N2O]2SeO4.H2O compound belongs tospace group C2/c. Selenium atom positions were located using SHELXS-97.28 The oxygen(O), carbon (C), and nitrogen (N) atom positions were deduced from difference Fouriermaps during the refinement. The hydrogen atoms of the CH2, NH2, CH, NH, and watermolecules have been fixed geometrically by appropriate instructions of the SHELXL-97program29 and held in the riding mode. The final discrepancy factors R1 and wR2 werefound to be 0.0375 and 0.0952, respectively. Crystal data and experimental parameters usedfor the intensity data collection are summarized in Table 4.

Crystallographic data for the structure reported in this work have been deposited intothe Cambridge Crystallographic Data Center as supplementary publication No. 899802.[Copies of the data can be obtained, free of charge, on application to the CCDC, 12 UnionRoad, Cambridge CB 12EZ, UK. E-mail deposit@ccdc.cam.ac.uk]

Physical Measurements

All NMR spectra were recorded on a Bruker DSX-300 spectrometer operating at75.47 MHz for 13C and 57.38 MHz for 77Se with a classical 4-mm probe head allowing

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BIS-(2-AMINO-3-BENZYLOXYPYRIDINIUM) SELENATE MONOHYDRATE 431

spinning rates up to 10 kHz. The chemical shifts were referenced relatively to tetramethyl-silane (TMS) and SeMe2 respectively. In all cases, it was checked that there was a sufficientdelay between the scans allowing a full relaxation of the nuclei.

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