Crystal Structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole

Authors

• Narsimha Reddy Penthala, University of Arkansas for Medical Sciences
• Jaishankar K. B. Yadlapalli, University of Arkansas for Medical Sciences
• Sean Parkin, University of KentuckyFollow
• Peter A. Crooks, University of Arkansas for Medical Sciences

Abstract

(Z)-5-[2-(Benzo[b]thio­phen-2-yl)-1-(3,5-di­meth­oxy­phen­yl)ethen­yl]-1H-tetrazole methanol monosolvate, C₁₉H₁₆N₄O₂S·CH₃OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thio­phen-2-yl)-2-(3,5-di­meth­oxy­phen­yl)acrylo­nitrile with tri­butyl­tin azide via a [3 + 2]cyclo­addition azide condensation reaction. The structurally related compound (Z)-5-[2-(benzo[b]thio­phen-3-yl)-1-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]-1H-tetra­zole, C₂₀H₁₈N₄O₃S, (II), was prepared by the reaction of (Z)-3-(benzo[b]thio­phen-3-yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­nitrile with tri­butyl­tin azide. Crystals of (I) have two mol­ecules in the asymmetric unit (Z′ = 2), whereas crystals of (II) have Z′ = 1. The benzo­thio­phene rings in (I) and (II) are almost planar, with r.m.s deviations from the mean plane of 0.0084 and 0.0037 Å in (I) and 0.0084 Å in (II). The tetra­zole rings of (I) and (II) make dihedral angles with the mean planes of the benzo­thio­phene rings of 88.81 (13) and 88.92 (13)° in (I), and 60.94 (6)° in (II). The di­meth­oxy­phenyl and tri­meth­oxy­phenyl rings make dihedral angles with the benzo­thio­phene rings of 23.91 (8) and 24.99 (8)° in (I) and 84.47 (3)° in (II). In both structures, mol­ecules are linked into hydrogen-bonded chains. In (I), these chains involve both tetra­zole and methanol, and are parallel to the b axis. In (II), mol­ecules are linked into chains parallel to the a axis by N—H⋯N hydrogen bonds between adjacent tetra­zole rings.

Document Type

Article

Publication Date

5-2016

Notes/Citation Information

Published in Acta Crystallographica Section E: Crystallographic Communications, v. 72, part 5, p. 652-655.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Digital Object Identifier (DOI)

https://doi.org/10.1107/S2056989016005600

Funding Information

The authors gratefully acknowledge the Arkansas Research Alliance for financial support, the UAMS sub award to PNR and SA from NIA Claude Pepper Center grant P30-AG028718 (J. Wei, P.I.) and the NIH/National Institute of General Medical Sciences (P20GM109005) for a COBRE award.

Related Content

Supporting information: this article has supporting information at journals.iucr.org/d.

CCDC references: 1472235; 1472234

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S2056989016005600/hg5472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016005600/hg5472Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S2056989016005600/hg5472IIsup3.hkl

checkCIF report

3D view of crystallographic information

Repository Citation

Penthala, Narsimha Reddy; Yadlapalli, Jaishankar K. B.; Parkin, Sean; and Crooks, Peter A., "Crystal Structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole" (2016). Chemistry Faculty Publications. 80.
https://uknowledge.uky.edu/chemistry_facpub/80