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

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 72; no. 5; pp. 652 - 655
• Main Authors: Penthala, Narsimha Reddy, Yadlapalli, Jaishankar K. B., Parkin, Sean, Crooks, Peter A.
• Format: Journal Article
• Language: English
• Published: 01.05.2016
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989016005600

( Z )-5-[2-(Benzo[ b ]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1 H -tetrazole methanol monosolvate, C 19 H 16 N 4 O 2 S·CH 3 OH, (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]-1 H -tetrazole, C 20 H 18 N 4 O 3 S, (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.