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

In the title compound, C(20)H(13)N(3)S, the partially saturated ring adopts a twisted half-boat conformation with the methyl­ene C atom closest to the amino­benzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydro­phenanthrene residue has a folded conformation...

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Autores principales: Al-Youbi, Abdulrahman O., Asiri, Abdullah M., Faidallah, Hassan M., 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/PMC3343991/
https://www.ncbi.nlm.nih.gov/pubmed/22589900
http://dx.doi.org/10.1107/S1600536812010033
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author Al-Youbi, Abdulrahman O.
Asiri, Abdullah M.
Faidallah, Hassan M.
Ng, Seik Weng
Tiekink, Edward R. T.
author_facet Al-Youbi, Abdulrahman O.
Asiri, Abdullah M.
Faidallah, Hassan M.
Ng, Seik Weng
Tiekink, Edward R. T.
author_sort Al-Youbi, Abdulrahman O.
collection PubMed
description In the title compound, C(20)H(13)N(3)S, the partially saturated ring adopts a twisted half-boat conformation with the methyl­ene C atom closest to the amino­benzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydro­phenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thio­phen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene ring to which it is attached. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R (2) (2)(12) loops. The dimers are linked into layers in the bc plane by weak C—H⋯π inter­actions. The thio­phen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio.
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spelling pubmed-33439912012-05-15 3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile Al-Youbi, Abdulrahman O. Asiri, Abdullah M. Faidallah, Hassan M. Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(20)H(13)N(3)S, the partially saturated ring adopts a twisted half-boat conformation with the methyl­ene C atom closest to the amino­benzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydro­phenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thio­phen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene ring to which it is attached. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R (2) (2)(12) loops. The dimers are linked into layers in the bc plane by weak C—H⋯π inter­actions. The thio­phen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio. International Union of Crystallography 2012-03-10 /pmc/articles/PMC3343991/ /pubmed/22589900 http://dx.doi.org/10.1107/S1600536812010033 Text en © Al-Youbi 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
Al-Youbi, Abdulrahman O.
Asiri, Abdullah M.
Faidallah, Hassan M.
Ng, Seik Weng
Tiekink, Edward R. T.
3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title 3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_full 3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_fullStr 3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_full_unstemmed 3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_short 3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
title_sort 3-amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3343991/
https://www.ncbi.nlm.nih.gov/pubmed/22589900
http://dx.doi.org/10.1107/S1600536812010033
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