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Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate

In the title compound, C(23)H(20)BrNO(4), the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r...

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Autores principales: El-Agrody, Ahmed M., Fouda, Ahmed M., Al-Omar, Mohamed A., Amr, Abd El-Galil E., Ng, Seik Weng, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588478/
https://www.ncbi.nlm.nih.gov/pubmed/23476606
http://dx.doi.org/10.1107/S160053681300490X
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author El-Agrody, Ahmed M.
Fouda, Ahmed M.
Al-Omar, Mohamed A.
Amr, Abd El-Galil E.
Ng, Seik Weng
Tiekink, Edward R. T.
author_facet El-Agrody, Ahmed M.
Fouda, Ahmed M.
Al-Omar, Mohamed A.
Amr, Abd El-Galil E.
Ng, Seik Weng
Tiekink, Edward R. T.
author_sort El-Agrody, Ahmed M.
collection PubMed
description In the title compound, C(23)H(20)BrNO(4), the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromo­benzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C—C—C—O = 3.4 (5)°]; the meth­oxy substituent is also coplanar [C—O—C—C = 174.5 (3)°]. In addition to an intra­molecular N—H⋯O(ester carbon­yl) hydrogen bond, the ester carbonyl O atom also forms an inter­molecular N—H⋯O hydrogen bond with the second amine H atom, generating a zigzag supra­molecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N—H⋯Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H⋯π inter­actions.
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spelling pubmed-35884782013-03-08 Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate El-Agrody, Ahmed M. Fouda, Ahmed M. Al-Omar, Mohamed A. Amr, Abd El-Galil E. Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(23)H(20)BrNO(4), the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromo­benzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C—C—C—O = 3.4 (5)°]; the meth­oxy substituent is also coplanar [C—O—C—C = 174.5 (3)°]. In addition to an intra­molecular N—H⋯O(ester carbon­yl) hydrogen bond, the ester carbonyl O atom also forms an inter­molecular N—H⋯O hydrogen bond with the second amine H atom, generating a zigzag supra­molecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N—H⋯Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H⋯π inter­actions. International Union of Crystallography 2013-02-23 /pmc/articles/PMC3588478/ /pubmed/23476606 http://dx.doi.org/10.1107/S160053681300490X Text en © El-Agrody et al. 2013 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
El-Agrody, Ahmed M.
Fouda, Ahmed M.
Al-Omar, Mohamed A.
Amr, Abd El-Galil E.
Ng, Seik Weng
Tiekink, Edward R. T.
Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate
title Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate
title_full Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate
title_fullStr Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate
title_full_unstemmed Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate
title_short Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate
title_sort ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4h-benzo[h]chromene-3-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588478/
https://www.ncbi.nlm.nih.gov/pubmed/23476606
http://dx.doi.org/10.1107/S160053681300490X
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