Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
In the title compounds, C24H22BrN3, (I), and C24H22ClN3, (II), the 2-aminopyridine ring is fused with a cycloheptane ring, which adopts a half-chair conformation. The planes of the phenyl and benzene rings are inclined to that of the central pyridine ring [r.m.s. deviations = 0.0083 (1) and 0.0093 (...
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International Union of Crystallography
2015-01-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989014025936 |
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| author | R. A. Nagalakshmi J. Suresh S. Maharani R. Ranjith Kumar P. L. Nilantha Lakshman |
| author_facet | R. A. Nagalakshmi J. Suresh S. Maharani R. Ranjith Kumar P. L. Nilantha Lakshman |
| author_sort | R. A. Nagalakshmi |
| collection | DOAJ |
| description | In the title compounds, C24H22BrN3, (I), and C24H22ClN3, (II), the 2-aminopyridine ring is fused with a cycloheptane ring, which adopts a half-chair conformation. The planes of the phenyl and benzene rings are inclined to that of the central pyridine ring [r.m.s. deviations = 0.0083 (1) and 0.0093 (1) Å for (I) and (II), respectively] by 62.47 (17) and 72.51 (14)°, respectively, in (I), and by 71.44 (9) and 54.90 (8)°, respectively, in (II). The planes of the aromatic rings are inclined to one another by 53.82 (17)° in (I) and by 58.04 (9)° in (II). In the crystals of both (I) and (II), pairs of N—H...Nnitrile hydrogen bonds link the molecules, forming inversion dimers with R22(12) ring motifs. In (I), the resulting dimers are connected through C—H...Br hydrogen bonds, forming sheets parallel to (10-1), and π–π interactions [inter-centroid distance = 3.7821 (16) Å] involving inversion-related pyridine rings, forming a three-dimensional network. In (II), the resulting dimers are connected through π–π interactions [inter-centroid distance = 3.771 (2) Å] involving inversion-related pyridine rings, forming a two-dimensional network lying parallel to (001). |
| first_indexed | 2024-12-22T07:42:18Z |
| format | Article |
| id | doaj.art-02e5fcae8fb44af0aace6d09356a3998 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-22T07:42:18Z |
| publishDate | 2015-01-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-02e5fcae8fb44af0aace6d09356a39982022-12-21T18:33:42ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902015-01-01711121510.1107/S2056989014025936su5027Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrileR. A. Nagalakshmi0J. Suresh1S. Maharani2R. Ranjith Kumar3P. L. Nilantha Lakshman4Department of Physics, The Madura College, Madurai 625 011, IndiaDepartment of Physics, The Madura College, Madurai 625 011, IndiaDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, IndiaDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, IndiaDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri LankaIn the title compounds, C24H22BrN3, (I), and C24H22ClN3, (II), the 2-aminopyridine ring is fused with a cycloheptane ring, which adopts a half-chair conformation. The planes of the phenyl and benzene rings are inclined to that of the central pyridine ring [r.m.s. deviations = 0.0083 (1) and 0.0093 (1) Å for (I) and (II), respectively] by 62.47 (17) and 72.51 (14)°, respectively, in (I), and by 71.44 (9) and 54.90 (8)°, respectively, in (II). The planes of the aromatic rings are inclined to one another by 53.82 (17)° in (I) and by 58.04 (9)° in (II). In the crystals of both (I) and (II), pairs of N—H...Nnitrile hydrogen bonds link the molecules, forming inversion dimers with R22(12) ring motifs. In (I), the resulting dimers are connected through C—H...Br hydrogen bonds, forming sheets parallel to (10-1), and π–π interactions [inter-centroid distance = 3.7821 (16) Å] involving inversion-related pyridine rings, forming a three-dimensional network. In (II), the resulting dimers are connected through π–π interactions [inter-centroid distance = 3.771 (2) Å] involving inversion-related pyridine rings, forming a two-dimensional network lying parallel to (001).http://scripts.iucr.org/cgi-bin/paper?S2056989014025936crystal structurecyclohepta[b]pyridinecarbonitrilehydrogen bondingπ–π interactions |
| spellingShingle | R. A. Nagalakshmi J. Suresh S. Maharani R. Ranjith Kumar P. L. Nilantha Lakshman Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile Acta Crystallographica Section E: Crystallographic Communications crystal structure cyclohepta[b]pyridine carbonitrile hydrogen bonding π–π interactions |
| title | Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile |
| title_full | Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile |
| title_fullStr | Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile |
| title_full_unstemmed | Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile |
| title_short | Crystal structures of 2-benzylamino-4-(4-bromophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-benzylamino-4-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile |
| title_sort | crystal structures of 2 benzylamino 4 4 bromophenyl 6 7 8 9 tetrahydro 5h cyclohepta b pyridine 3 carbonitrile and 2 benzylamino 4 4 chlorophenyl 6 7 8 9 tetrahydro 5h cyclohepta b pyridine 3 carbonitrile |
| topic | crystal structure cyclohepta[b]pyridine carbonitrile hydrogen bonding π–π interactions |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989014025936 |
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