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A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid
Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally by the hydrothermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)methyl]isophthalic acid with manganese chloride tetrahydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2012
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515175/ https://www.ncbi.nlm.nih.gov/pubmed/23284402 http://dx.doi.org/10.1107/S1600536812041025 |
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author | Kuai, Hai-Wei |
author_facet | Kuai, Hai-Wei |
author_sort | Kuai, Hai-Wei |
collection | PubMed |
description | Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally by the hydrothermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)methyl]isophthalic acid with manganese chloride tetrahydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously from a similar reaction [Cheng (2011 ▶). Acta Cryst. E67, o3299]. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.020 (4) Å. The benzimidazole unit and benzene ring are inclined at a dihedral angle of 68.17 (4)°, reflecting the axial rotation of the flexible benzimidazolyl arm. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent molecules into inversion dimers. O—H⋯N contacts connect these dimers into zigzag chains along [010]. |
format | Online Article Text |
id | pubmed-3515175 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-35151752013-01-02 A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid Kuai, Hai-Wei Acta Crystallogr Sect E Struct Rep Online Organic Papers Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally by the hydrothermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)methyl]isophthalic acid with manganese chloride tetrahydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously from a similar reaction [Cheng (2011 ▶). Acta Cryst. E67, o3299]. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.020 (4) Å. The benzimidazole unit and benzene ring are inclined at a dihedral angle of 68.17 (4)°, reflecting the axial rotation of the flexible benzimidazolyl arm. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent molecules into inversion dimers. O—H⋯N contacts connect these dimers into zigzag chains along [010]. International Union of Crystallography 2012-10-06 /pmc/articles/PMC3515175/ /pubmed/23284402 http://dx.doi.org/10.1107/S1600536812041025 Text en © Hai-Wei Kuai 2012 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 A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid |
title | A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid |
title_full | A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid |
title_fullStr | A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid |
title_full_unstemmed | A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid |
title_short | A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid |
title_sort | monoclinic polymorph of 5-[(1h-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3515175/ https://www.ncbi.nlm.nih.gov/pubmed/23284402 http://dx.doi.org/10.1107/S1600536812041025 |
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