Cargando…
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...
Autores principales: | , , , , , , |
---|---|
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 |
_version_ | 1783278296858886144 |
---|---|
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. |
format | Online Article Text |
id | pubmed-5683510 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT anhletuan unusualthermolysisofazacyclicalleneundermicrowaveconditionscrystalstructureof3rs3asr8rs8arsmethyl56dimethoxy3a10dimethyl1phenyl33a88atetrahydro38epiminomethanocyclopentaaindene2carboxylatefromsynchrotronxraydiffraction AT titovalexandera unusualthermolysisofazacyclicalleneundermicrowaveconditionscrystalstructureof3rs3asr8rs8arsmethyl56dimethoxy3a10dimethyl1phenyl33a88atetrahydro38epiminomethanocyclopentaaindene2carboxylatefromsynchrotronxraydiffraction AT kobzevmaxims unusualthermolysisofazacyclicalleneundermicrowaveconditionscrystalstructureof3rs3asr8rs8arsmethyl56dimethoxy3a10dimethyl1phenyl33a88atetrahydro38epiminomethanocyclopentaaindene2carboxylatefromsynchrotronxraydiffraction AT voskressenskyleonidg unusualthermolysisofazacyclicalleneundermicrowaveconditionscrystalstructureof3rs3asr8rs8arsmethyl56dimethoxy3a10dimethyl1phenyl33a88atetrahydro38epiminomethanocyclopentaaindene2carboxylatefromsynchrotronxraydiffraction AT varlamovalexeyv unusualthermolysisofazacyclicalleneundermicrowaveconditionscrystalstructureof3rs3asr8rs8arsmethyl56dimethoxy3a10dimethyl1phenyl33a88atetrahydro38epiminomethanocyclopentaaindene2carboxylatefromsynchrotronxraydiffraction AT dorovatovskiipavelv unusualthermolysisofazacyclicalleneundermicrowaveconditionscrystalstructureof3rs3asr8rs8arsmethyl56dimethoxy3a10dimethyl1phenyl33a88atetrahydro38epiminomethanocyclopentaaindene2carboxylatefromsynchrotronxraydiffraction AT khrustalevvictorn unusualthermolysisofazacyclicalleneundermicrowaveconditionscrystalstructureof3rs3asr8rs8arsmethyl56dimethoxy3a10dimethyl1phenyl33a88atetrahydro38epiminomethanocyclopentaaindene2carboxylatefromsynchrotronxraydiffraction |