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Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction

The title compound, C(25)H(27)NO(4) (I), the product of the unusual thermolysis of aza­cyclic allene methyl 10,11-dimeth­oxy-3,8-dimethyl-6-phenyl-3-aza­benzo[d]cyclo­deca-4,6,7-triene-5-carboxyl­ate, represents a bicyclic heterosystem and crystallizes in the monoclinic space group P2(1)/c with thre...

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Autores principales: Anh, Le Tuan, Titov, Alexander A., Kobzev, Maxim S., Voskressensky, Leonid G., Varlamov, Alexey V., Dorovatovskii, Pavel V., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683510/
https://www.ncbi.nlm.nih.gov/pubmed/29152370
http://dx.doi.org/10.1107/S2056989017014864
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author Anh, Le Tuan
Titov, Alexander A.
Kobzev, Maxim S.
Voskressensky, Leonid G.
Varlamov, Alexey V.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_facet Anh, Le Tuan
Titov, Alexander A.
Kobzev, Maxim S.
Voskressensky, Leonid G.
Varlamov, Alexey V.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_sort Anh, Le Tuan
collection PubMed
description The title compound, C(25)H(27)NO(4) (I), the product of the unusual thermolysis of aza­cyclic allene methyl 10,11-dimeth­oxy-3,8-dimethyl-6-phenyl-3-aza­benzo[d]cyclo­deca-4,6,7-triene-5-carboxyl­ate, represents a bicyclic heterosystem and crystallizes in the monoclinic space group P2(1)/c with three crystallographically independent mol­ecules in the unit cell. These independent mol­ecules adopt very similar geometries and differ only in the conformations of the two meth­oxy substituents on the benzene ring. In two of the three independent mol­ecules, both meth­oxy groups are almost coplanar with the benzene ring [the C—C—O—Me torsion angles are 10.8 (2), 12.3 (2), 9.1 (2) and 13.6 (3)°], whereas in the third mol­ecule, one of the meth­oxy groups is practically coplanar to and the other meth­oxy group is roughly perpendicular to the benzene ring, the C—C—O—Me torsion angles being 14.1 (2) and 76.5 (2)°. The mol­ecule of (I) comprises a fused tetra­cyclic system containing two five-membered rings (cyclo­pentenes) and two six-membered rings (piperidine and benzene). The five-membered rings have the usual envelope conformation, with the methyl-subsituted C atom as the flap in each molecule, and the six-membered piperidine ring has a chair conformation. The methyl substituent at the N atom occupies the sterically favourable equatorial position. The carboxyl­ate group lies almost within the basal plane of the parent cyclo­pentene ring [making dihedral angle of 11.68 (8), 18.94 (9) and 15.16 (9)° in the three independent mol­ecules], while the phenyl substituent is twisted by 48.26 (6), 42.04 (6) and 41.28 (6)° (for the three independent mol­ecules) relative to this plane. In the crystal, mol­ecules of (I) form stacks along the b-axis direction. The mol­ecules are arranged at van der Waals distances.
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spelling pubmed-56835102017-11-17 Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction Anh, Le Tuan Titov, Alexander A. Kobzev, Maxim S. Voskressensky, Leonid G. Varlamov, Alexey V. Dorovatovskii, Pavel V. Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(25)H(27)NO(4) (I), the product of the unusual thermolysis of aza­cyclic allene methyl 10,11-dimeth­oxy-3,8-dimethyl-6-phenyl-3-aza­benzo[d]cyclo­deca-4,6,7-triene-5-carboxyl­ate, represents a bicyclic heterosystem and crystallizes in the monoclinic space group P2(1)/c with three crystallographically independent mol­ecules in the unit cell. These independent mol­ecules adopt very similar geometries and differ only in the conformations of the two meth­oxy substituents on the benzene ring. In two of the three independent mol­ecules, both meth­oxy groups are almost coplanar with the benzene ring [the C—C—O—Me torsion angles are 10.8 (2), 12.3 (2), 9.1 (2) and 13.6 (3)°], whereas in the third mol­ecule, one of the meth­oxy groups is practically coplanar to and the other meth­oxy group is roughly perpendicular to the benzene ring, the C—C—O—Me torsion angles being 14.1 (2) and 76.5 (2)°. The mol­ecule of (I) comprises a fused tetra­cyclic system containing two five-membered rings (cyclo­pentenes) and two six-membered rings (piperidine and benzene). The five-membered rings have the usual envelope conformation, with the methyl-subsituted C atom as the flap in each molecule, and the six-membered piperidine ring has a chair conformation. The methyl substituent at the N atom occupies the sterically favourable equatorial position. The carboxyl­ate group lies almost within the basal plane of the parent cyclo­pentene ring [making dihedral angle of 11.68 (8), 18.94 (9) and 15.16 (9)° in the three independent mol­ecules], while the phenyl substituent is twisted by 48.26 (6), 42.04 (6) and 41.28 (6)° (for the three independent mol­ecules) relative to this plane. In the crystal, mol­ecules of (I) form stacks along the b-axis direction. The mol­ecules are arranged at van der Waals distances. International Union of Crystallography 2017-10-24 /pmc/articles/PMC5683510/ /pubmed/29152370 http://dx.doi.org/10.1107/S2056989017014864 Text en © Anh et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Anh, Le Tuan
Titov, Alexander A.
Kobzev, Maxim S.
Voskressensky, Leonid G.
Varlamov, Alexey V.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction
title Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction
title_full Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction
title_fullStr Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction
title_full_unstemmed Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction
title_short Unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3RS,3aSR,8RS,8aRS)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron X-ray diffraction
title_sort unusual thermolysis of aza­cyclic allene under microwave conditions: crystal structure of (3rs,3asr,8rs,8ars)-methyl 5,6-dimeth­oxy-3a,10-dimethyl-1-phenyl-3,3a,8,8a-tetra­hydro-3,8-(epimino­methano)­cyclo­penta­[a]indene-2-carboxyl­ate from synchrotron x-ray diffraction
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683510/
https://www.ncbi.nlm.nih.gov/pubmed/29152370
http://dx.doi.org/10.1107/S2056989017014864
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