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2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane

The title compound, C(16)H(12)BClN(2), is one in a series of diaza­borinanes, derived from 1,8-diaminona­phthalene, featuring substitution at the 1, 2 and 3 positions in the nitro­gen-boron heterocycle. The structure deviates from planarity, the torsion angle subtended by the p-chloro­phenyl ring re...

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Detalles Bibliográficos
Autores principales: Akerman, Matthew P., Robinson, Ross S., Slabber, Cathryn A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3212269/
https://www.ncbi.nlm.nih.gov/pubmed/22090926
http://dx.doi.org/10.1107/S1600536811025487
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author Akerman, Matthew P.
Robinson, Ross S.
Slabber, Cathryn A.
author_facet Akerman, Matthew P.
Robinson, Ross S.
Slabber, Cathryn A.
author_sort Akerman, Matthew P.
collection PubMed
description The title compound, C(16)H(12)BClN(2), is one in a series of diaza­borinanes, derived from 1,8-diaminona­phthalene, featuring substitution at the 1, 2 and 3 positions in the nitro­gen-boron heterocycle. The structure deviates from planarity, the torsion angle subtended by the p-chloro­phenyl ring relative to the nitro­gen–boron heterocycle being −44-.3(3)°. The mol­ecules form infinite chains with strong inter­actions between the vacant pz orbital of the B atom and the π-system of an adjacent mol­ecule. The distance between the B atom and the 10-atom centroid of an adjacent naphthalene ring is 3.381 (4) Å. One N-H H atom is weakly hydrogen bonded to the Cl atom of an adjacent mol­ecule. This combination of inter­molecular inter­actions leads to the formation of an infinite two-dimensional network perpendic­ular to the c axis.
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spelling pubmed-32122692011-11-16 2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane Akerman, Matthew P. Robinson, Ross S. Slabber, Cathryn A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(16)H(12)BClN(2), is one in a series of diaza­borinanes, derived from 1,8-diaminona­phthalene, featuring substitution at the 1, 2 and 3 positions in the nitro­gen-boron heterocycle. The structure deviates from planarity, the torsion angle subtended by the p-chloro­phenyl ring relative to the nitro­gen–boron heterocycle being −44-.3(3)°. The mol­ecules form infinite chains with strong inter­actions between the vacant pz orbital of the B atom and the π-system of an adjacent mol­ecule. The distance between the B atom and the 10-atom centroid of an adjacent naphthalene ring is 3.381 (4) Å. One N-H H atom is weakly hydrogen bonded to the Cl atom of an adjacent mol­ecule. This combination of inter­molecular inter­actions leads to the formation of an infinite two-dimensional network perpendic­ular to the c axis. International Union of Crystallography 2011-07-02 /pmc/articles/PMC3212269/ /pubmed/22090926 http://dx.doi.org/10.1107/S1600536811025487 Text en © Akerman et al. 2011 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
Akerman, Matthew P.
Robinson, Ross S.
Slabber, Cathryn A.
2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane
title 2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane
title_full 2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane
title_fullStr 2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane
title_full_unstemmed 2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane
title_short 2-(4-Chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane
title_sort 2-(4-chloro­phen­yl)naphtho­[1,8-de][1,3,2]diaza­borinane
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3212269/
https://www.ncbi.nlm.nih.gov/pubmed/22090926
http://dx.doi.org/10.1107/S1600536811025487
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