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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...

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Autores principales: Saad, Syed Muhammad, Haider, Syed Moazzam, Perveen, Shahnaz, Khan, Khalid M., Yousuf, Sammer
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
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.
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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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