Cargando…
Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione
The title compound, C(17)H(18)N(2)O(3), is constructed from a benzodiazepine ring system linked to a pendant dihydropyran ring, where the benzene and pendant dihydropyran rings are oriented at a dihedral angle of 15.14 (4)°. Intramolecular N—H(Diazp)⋯O(Dhydp) and C—H(Diazp)⋯O(Dhydp) (Diazp = di...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6362647/ https://www.ncbi.nlm.nih.gov/pubmed/30800456 http://dx.doi.org/10.1107/S2056989019000689 |
_version_ | 1783392962315550720 |
---|---|
author | Samba, Mohamed Minnih, Mohamed Said Hökelek, Tuncer Kaur, Manpreet Jasinski, Jerry P. Sebbar, Nada Kheira Essassi, El Mokhtar |
author_facet | Samba, Mohamed Minnih, Mohamed Said Hökelek, Tuncer Kaur, Manpreet Jasinski, Jerry P. Sebbar, Nada Kheira Essassi, El Mokhtar |
author_sort | Samba, Mohamed |
collection | PubMed |
description | The title compound, C(17)H(18)N(2)O(3), is constructed from a benzodiazepine ring system linked to a pendant dihydropyran ring, where the benzene and pendant dihydropyran rings are oriented at a dihedral angle of 15.14 (4)°. Intramolecular N—H(Diazp)⋯O(Dhydp) and C—H(Diazp)⋯O(Dhydp) (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bonds link the seven-membered diazepine ring to the pendant dihydropyran ring, enclosing S(6) ring motifs. In the crystal, N—H(Diazp)⋯O(Dhydp) hydrogen bonds link the molecules into infinite chains along [10[Image: see text]]. These chains are further linked via C—H(Bnz)⋯O(Dhydp), C—H(Dhydp)⋯O(Dhydp) and C—H(Mth)⋯O(Dhydp) (Bnz = benzene and Mth = methyl) hydrogen bonds, forming a three-dimensional network. The observed weak C—H(Diazp) ⋯ π interaction may further stabilize the structure. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (51.1%), H⋯C/C⋯H (25.3%) and H⋯O/O⋯H (20.3%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. |
format | Online Article Text |
id | pubmed-6362647 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-63626472019-02-22 Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione Samba, Mohamed Minnih, Mohamed Said Hökelek, Tuncer Kaur, Manpreet Jasinski, Jerry P. Sebbar, Nada Kheira Essassi, El Mokhtar Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(17)H(18)N(2)O(3), is constructed from a benzodiazepine ring system linked to a pendant dihydropyran ring, where the benzene and pendant dihydropyran rings are oriented at a dihedral angle of 15.14 (4)°. Intramolecular N—H(Diazp)⋯O(Dhydp) and C—H(Diazp)⋯O(Dhydp) (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bonds link the seven-membered diazepine ring to the pendant dihydropyran ring, enclosing S(6) ring motifs. In the crystal, N—H(Diazp)⋯O(Dhydp) hydrogen bonds link the molecules into infinite chains along [10[Image: see text]]. These chains are further linked via C—H(Bnz)⋯O(Dhydp), C—H(Dhydp)⋯O(Dhydp) and C—H(Mth)⋯O(Dhydp) (Bnz = benzene and Mth = methyl) hydrogen bonds, forming a three-dimensional network. The observed weak C—H(Diazp) ⋯ π interaction may further stabilize the structure. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (51.1%), H⋯C/C⋯H (25.3%) and H⋯O/O⋯H (20.3%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. International Union of Crystallography 2019-01-18 /pmc/articles/PMC6362647/ /pubmed/30800456 http://dx.doi.org/10.1107/S2056989019000689 Text en © Samba et al. 2019 http://creativecommons.org/licenses/by/4.0/ 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/4.0/ |
spellingShingle | Research Communications Samba, Mohamed Minnih, Mohamed Said Hökelek, Tuncer Kaur, Manpreet Jasinski, Jerry P. Sebbar, Nada Kheira Essassi, El Mokhtar Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione |
title | Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione |
title_full | Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione |
title_fullStr | Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione |
title_full_unstemmed | Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione |
title_short | Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione |
title_sort | synthesis, crystal structure and hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1h-1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2h-pyran-2,4-dione |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6362647/ https://www.ncbi.nlm.nih.gov/pubmed/30800456 http://dx.doi.org/10.1107/S2056989019000689 |
work_keys_str_mv | AT sambamohamed synthesiscrystalstructureandhirshfeldsurfaceanalysisof344dimethyl2345tetrahydro1h15benzodiazepin2ylidene6methyl34dihydro2hpyran24dione AT minnihmohamedsaid synthesiscrystalstructureandhirshfeldsurfaceanalysisof344dimethyl2345tetrahydro1h15benzodiazepin2ylidene6methyl34dihydro2hpyran24dione AT hokelektuncer synthesiscrystalstructureandhirshfeldsurfaceanalysisof344dimethyl2345tetrahydro1h15benzodiazepin2ylidene6methyl34dihydro2hpyran24dione AT kaurmanpreet synthesiscrystalstructureandhirshfeldsurfaceanalysisof344dimethyl2345tetrahydro1h15benzodiazepin2ylidene6methyl34dihydro2hpyran24dione AT jasinskijerryp synthesiscrystalstructureandhirshfeldsurfaceanalysisof344dimethyl2345tetrahydro1h15benzodiazepin2ylidene6methyl34dihydro2hpyran24dione AT sebbarnadakheira synthesiscrystalstructureandhirshfeldsurfaceanalysisof344dimethyl2345tetrahydro1h15benzodiazepin2ylidene6methyl34dihydro2hpyran24dione AT essassielmokhtar synthesiscrystalstructureandhirshfeldsurfaceanalysisof344dimethyl2345tetrahydro1h15benzodiazepin2ylidene6methyl34dihydro2hpyran24dione |