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2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile
The title molecule, C(10)H(10)N(4)O(2), is almost planar and adopts an E configuration of the azomethine [C=N = 1.298 (2) Å] double bond. The benzene ring is attached to an essentially planar (r.m.s. deviation = 0.0226 Å) amidine moiety (N=CN/Me(2)), the dihedral angle between the two mean planes b...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588379/ https://www.ncbi.nlm.nih.gov/pubmed/23476456 http://dx.doi.org/10.1107/S1600536812048866 |
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author | Saad, Syed Muhammad Haider, Syed Moazzam Perveen, Shahnaz Khan, Khalid M. Yousuf, Sammer |
author_facet | Saad, Syed Muhammad Haider, Syed Moazzam Perveen, Shahnaz Khan, Khalid M. Yousuf, Sammer |
author_sort | Saad, Syed Muhammad |
collection | PubMed |
description | The title molecule, C(10)H(10)N(4)O(2), is almost planar and adopts an E configuration of the azomethine [C=N = 1.298 (2) Å] double bond. The benzene ring is attached to an essentially planar (r.m.s. deviation = 0.0226 Å) amidine moiety (N=CN/Me(2)), the dihedral angle between the two mean planes being 18.42 (11)°. The cyano group lies in the plane of the benzene ring [the C and N atoms deviating by 0.030 (3) and 0.040 (3) Å, respectively], while the nitro group makes a dihedral angle 5.8 (3)° with the benzene ring. There are two distinct intermolecular hydrogen bonds, C—H⋯O and C—H⋯N, that stabilize the crystal structure; the former interactions result in centrosymmetric dimers about inversion centers resulting in ten-membered rings, while the later give rise to chains of molecules running parallel to the b axis. |
format | Online Article Text |
id | pubmed-3588379 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-35883792013-03-08 2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile Saad, Syed Muhammad Haider, Syed Moazzam Perveen, Shahnaz Khan, Khalid M. Yousuf, Sammer Acta Crystallogr Sect E Struct Rep Online Organic Papers The title molecule, C(10)H(10)N(4)O(2), is almost planar and adopts an E configuration of the azomethine [C=N = 1.298 (2) Å] double bond. The benzene ring is attached to an essentially planar (r.m.s. deviation = 0.0226 Å) amidine moiety (N=CN/Me(2)), the dihedral angle between the two mean planes being 18.42 (11)°. The cyano group lies in the plane of the benzene ring [the C and N atoms deviating by 0.030 (3) and 0.040 (3) Å, respectively], while the nitro group makes a dihedral angle 5.8 (3)° with the benzene ring. There are two distinct intermolecular hydrogen bonds, C—H⋯O and C—H⋯N, that stabilize the crystal structure; the former interactions result in centrosymmetric dimers about inversion centers resulting in ten-membered rings, while the later give rise to chains of molecules running parallel to the b axis. International Union of Crystallography 2012-12-12 /pmc/articles/PMC3588379/ /pubmed/23476456 http://dx.doi.org/10.1107/S1600536812048866 Text en © Saad et al. 2013 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 Saad, Syed Muhammad Haider, Syed Moazzam Perveen, Shahnaz Khan, Khalid M. Yousuf, Sammer 2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile |
title | 2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile |
title_full | 2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile |
title_fullStr | 2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile |
title_full_unstemmed | 2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile |
title_short | 2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile |
title_sort | 2-{[(dimethylamino)methylidene]amino}-5-nitrobenzonitrile |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588379/ https://www.ncbi.nlm.nih.gov/pubmed/23476456 http://dx.doi.org/10.1107/S1600536812048866 |
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