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, C17H18N2O3, 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—HDiazp...ODhydp and C—HDiazp...ODhydp (Diazp = diazepine and Dhydp...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019000689 |
| _version_ | 1818957936989306880 |
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| author | Mohamed Samba Mohamed Said Minnih Tuncer Hökelek Manpreet Kaur Jerry P. Jasinski Nada Kheira Sebbar El Mokhtar Essassi |
| author_facet | Mohamed Samba Mohamed Said Minnih Tuncer Hökelek Manpreet Kaur Jerry P. Jasinski Nada Kheira Sebbar El Mokhtar Essassi |
| author_sort | Mohamed Samba |
| collection | DOAJ |
| description | The title compound, C17H18N2O3, 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—HDiazp...ODhydp and C—HDiazp...ODhydp (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—HDiazp...ODhydp hydrogen bonds link the molecules into infinite chains along [10\overline{1}]. These chains are further linked via C—HBnz...ODhydp, C—HDhydp...ODhydp and C—HMth...ODhydp (Bnz = benzene and Mth = methyl) hydrogen bonds, forming a three-dimensional network. The observed weak C—HDiazp ... 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. |
| first_indexed | 2024-12-20T11:17:47Z |
| format | Article |
| id | doaj.art-37a6109d07ce40b49f8b2a07e6ebd5f2 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T11:17:47Z |
| publishDate | 2019-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-37a6109d07ce40b49f8b2a07e6ebd5f22022-12-21T19:42:34ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-02-0175222823210.1107/S2056989019000689lh5890Synthesis, 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-dioneMohamed Samba0Mohamed Said Minnih1Tuncer Hökelek2Manpreet Kaur3Jerry P. Jasinski4Nada Kheira Sebbar5El Mokhtar Essassi6Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, TurkeyDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, IndiaDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USALaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoThe title compound, C17H18N2O3, 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—HDiazp...ODhydp and C—HDiazp...ODhydp (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—HDiazp...ODhydp hydrogen bonds link the molecules into infinite chains along [10\overline{1}]. These chains are further linked via C—HBnz...ODhydp, C—HDhydp...ODhydp and C—HMth...ODhydp (Bnz = benzene and Mth = methyl) hydrogen bonds, forming a three-dimensional network. The observed weak C—HDiazp ... 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.http://scripts.iucr.org/cgi-bin/paper?S2056989019000689crystal structurebenzodiazepinehydrogen bondHirshfeld surface |
| spellingShingle | Mohamed Samba Mohamed Said Minnih Tuncer Hökelek Manpreet Kaur Jerry P. Jasinski Nada Kheira Sebbar El Mokhtar Essassi 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 Acta Crystallographica Section E: Crystallographic Communications crystal structure benzodiazepine hydrogen bond Hirshfeld surface |
| 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 | crystal structure benzodiazepine hydrogen bond Hirshfeld surface |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019000689 |
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