Crystal structure of {l-benzyI-2-[(4-nitrobenzyI)sulfanyl]-1H-imidazol-5-yl}- methanol, C18H17N3O3S

Abstract

Experimental detailsThe strong anisotropy for some atoms is caused by i) the libration of the nitro group and ii) an empty small hole in the structure (figure, bottom). These factors and a poor quality of the crystal lead to a large amount of weak reflections and to unusually high R values. DiscussionImidazole derivatives exhibit antibacterial and antifungal activity [1,2]. In recent years there has been increasing interest in the determination of crystal structures for biologically active compounds [3][4][5][6][7][8][9]. In the crystal structure of the title compound, the covalent bonds are found to be normal. , ¿03-C11-C10= 114.1(3)°, ¿C8^3-C10= 107.2°, ZC8-N2-C9 = 104.6(3)° arc almost similar to previous reports [7][8][9]. The torsion angles Z.C5-C6-C7-S1, ¿C7-S1-C8-N3, ¿C8-N3-C12-C13 and ¿N3-C12-C13-C14 (56.7(5)°, -157.7(3)°, -94.9(4)° and 26.6(5)°, respectively) show clearly that the three rings do not share a common plane probably as a result of electrostatic repulsive and steric interactions [7][8][9]. The torsion angle ¿C8-S1-C7-C6 is 68.8(3)°, indicating that the conformation along SI-C7 bond is approximately gauche (synclinal). It seems that in this conformer electrostatic repulsive and steric interactions in the molecule packing are in a minimum. Intermolecular ring stacking is observed within the crystals probably as a result of the presence of parallel aromatic rings in the crystal network. Intermolecular hydrogen bonding between H Abstract C18H17N3O3S, monoclinic, P12i/cl (no. 14), a = 15.705(2) A, b = 12.083(2) A, c = 9.368(1) A, P = 102.404(3)°, V = 1736.3 A 3 , Z = 4, R gl (F) = 0.078, wR^F 2 ) = 0.226, T= 120 K.Source of material {1 -benzyl-2-[(4-nitrobenzyl)sulfanyl]-1 ii-imidazol-5-yl} methanol, was synthesized in accordance with the published procedure [1,2]. Single crystals of the tide compound were prepared from a mixture of n-hexane/dioxan (5:1) at 322 K during five weeks using the branch tube method. The colorless crystals were filtered off, washed with a cold mixture of w-hexane/dioxan (5:1, 8 ml) and dried in vacuum over P4O10 (m.p. 522 K). Elemental analysis: found -C, 60.79 %; H, 4.77 %; N, 11.78 %, calc. for C18H17N3O3S -C, 60.83 %; H, 4.82 %; N, 11.82 %. Melting point was measured on an Electrothermal 9100 apparatus and is uncorrected. Elemental analysis was performed using a Heraeus CHN-O-Rapid analyzer.