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Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid

Three polymorphs of the title compound, C(15)H(12)N(2)O(2), were obtained accidentally as single crystals in the hydro­thermal reaction of the title compound with manganese bromide in the presence of N,N′-dimethyl­formamide at 373 K. Here we report the structure of the first polymorph. The benzimida...

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Autores principales: Kuai, Hai-Wei, Cheng, Xiao-Chun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201311/
https://www.ncbi.nlm.nih.gov/pubmed/22058821
http://dx.doi.org/10.1107/S1600536811039043
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author Kuai, Hai-Wei
Cheng, Xiao-Chun
author_facet Kuai, Hai-Wei
Cheng, Xiao-Chun
author_sort Kuai, Hai-Wei
collection PubMed
description Three polymorphs of the title compound, C(15)H(12)N(2)O(2), were obtained accidentally as single crystals in the hydro­thermal reaction of the title compound with manganese bromide in the presence of N,N′-dimethyl­formamide at 373 K. Here we report the structure of the first polymorph. The benzimidazole ring is almost planar, the maximum deviation from the mean plane being 0.016 (1) Å. The benzimidazole and benzene rings are approximately perpendicular, making a dihedral angle 85.56 (7)°, which is a reflection of the axial rotation of the flexible benzimidazolyl arm. In the crystal, adjacent mol­ecules are connected through O—H⋯N hydrogen bonds into a chain along [100], and neighboring chains are further linked by via weak C—H⋯O hydrogen-bonding inter­actions, forming a two-dimensional network.
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spelling pubmed-32013112011-11-06 Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid Kuai, Hai-Wei Cheng, Xiao-Chun Acta Crystallogr Sect E Struct Rep Online Organic Papers Three polymorphs of the title compound, C(15)H(12)N(2)O(2), were obtained accidentally as single crystals in the hydro­thermal reaction of the title compound with manganese bromide in the presence of N,N′-dimethyl­formamide at 373 K. Here we report the structure of the first polymorph. The benzimidazole ring is almost planar, the maximum deviation from the mean plane being 0.016 (1) Å. The benzimidazole and benzene rings are approximately perpendicular, making a dihedral angle 85.56 (7)°, which is a reflection of the axial rotation of the flexible benzimidazolyl arm. In the crystal, adjacent mol­ecules are connected through O—H⋯N hydrogen bonds into a chain along [100], and neighboring chains are further linked by via weak C—H⋯O hydrogen-bonding inter­actions, forming a two-dimensional network. International Union of Crystallography 2011-09-30 /pmc/articles/PMC3201311/ /pubmed/22058821 http://dx.doi.org/10.1107/S1600536811039043 Text en © Kuai and Cheng 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Kuai, Hai-Wei
Cheng, Xiao-Chun
Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid
title Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid
title_full Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid
title_fullStr Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid
title_full_unstemmed Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid
title_short Monoclinic polymorph of 4-[(1H-benz­imidazol-1-yl)meth­yl]benzoic acid
title_sort monoclinic polymorph of 4-[(1h-benz­imidazol-1-yl)meth­yl]benzoic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201311/
https://www.ncbi.nlm.nih.gov/pubmed/22058821
http://dx.doi.org/10.1107/S1600536811039043
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