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3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

In the title compound, C(24)H(19)N(3)O(2), the partially saturated ring adopts a distorted half-chair conformation with the methyl­ene-C atom closest to the amino­benzene ring lying 0.664 (3) Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.1429 Å. The dihedral angle [32....

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Autores principales: Asiri, Abdullah M., Faidallah, Hassan M., Alamry, Khalid A., Ng, Seik Weng, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344065/
https://www.ncbi.nlm.nih.gov/pubmed/22589974
http://dx.doi.org/10.1107/S1600536812011129
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author Asiri, Abdullah M.
Faidallah, Hassan M.
Alamry, Khalid A.
Ng, Seik Weng
Tiekink, Edward R. T.
author_facet Asiri, Abdullah M.
Faidallah, Hassan M.
Alamry, Khalid A.
Ng, Seik Weng
Tiekink, Edward R. T.
author_sort Asiri, Abdullah M.
collection PubMed
description In the title compound, C(24)H(19)N(3)O(2), the partially saturated ring adopts a distorted half-chair conformation with the methyl­ene-C atom closest to the amino­benzene ring lying 0.664 (3) Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.1429 Å. The dihedral angle [32.01 (10)°] between the benzene rings on either side of this ring indicates a significant fold in this part of the mol­ecule. The dimeth­oxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03 (9)°]. The mol­ecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873–o2873]. Supra­molecular chains with base vector [201] are formed in the crystal structure via N—H⋯O hydrogen bonds between the amino H atoms of one mol­ecule inter­acting with the meth­oxy O atoms of a neighbouring mol­ecule. The chains are linked into a three-dimensional architecture by C—H⋯π inter­actions.
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spelling pubmed-33440652012-05-15 3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile Asiri, Abdullah M. Faidallah, Hassan M. Alamry, Khalid A. Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(24)H(19)N(3)O(2), the partially saturated ring adopts a distorted half-chair conformation with the methyl­ene-C atom closest to the amino­benzene ring lying 0.664 (3) Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.1429 Å. The dihedral angle [32.01 (10)°] between the benzene rings on either side of this ring indicates a significant fold in this part of the mol­ecule. The dimeth­oxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03 (9)°]. The mol­ecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873–o2873]. Supra­molecular chains with base vector [201] are formed in the crystal structure via N—H⋯O hydrogen bonds between the amino H atoms of one mol­ecule inter­acting with the meth­oxy O atoms of a neighbouring mol­ecule. The chains are linked into a three-dimensional architecture by C—H⋯π inter­actions. International Union of Crystallography 2012-03-21 /pmc/articles/PMC3344065/ /pubmed/22589974 http://dx.doi.org/10.1107/S1600536812011129 Text en © Asiri et al. 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
Asiri, Abdullah M.
Faidallah, Hassan M.
Alamry, Khalid A.
Ng, Seik Weng
Tiekink, Edward R. T.
3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title 3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_full 3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_fullStr 3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_full_unstemmed 3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_short 3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_sort 3-amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344065/
https://www.ncbi.nlm.nih.gov/pubmed/22589974
http://dx.doi.org/10.1107/S1600536812011129
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