Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine
The title compound, C12H11N3O2, is a second monoclinic polymorph (P21, with Z′ = 4) of the previously reported monoclinic (P21/c, with Z′ = 2) form [Akhmad Aznan et al. (2010). Acta Cryst. E66, o2400]. Four independent molecules comprise the asymmetric unit, which have the common features of a syn d...
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International Union of Crystallography
2014-08-01
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| Series: | Acta Crystallographica Section E |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536814012227 |
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doaj-51a5e860b30542109fc5e59aadec81cd2020-11-25T01:56:27ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682014-08-01708586110.1107/S1600536814012227hb0011Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amineAina Mardia Akhmad Aznan0Zanariah Abdullah1Vannajan Sanghiran Lee2Edward R. T. Tiekink3Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaThe title compound, C12H11N3O2, is a second monoclinic polymorph (P21, with Z′ = 4) of the previously reported monoclinic (P21/c, with Z′ = 2) form [Akhmad Aznan et al. (2010). Acta Cryst. E66, o2400]. Four independent molecules comprise the asymmetric unit, which have the common features of a syn disposition of the pyridine N atom and the toluene ring, and an intramolecular amine–nitro N—H...O hydrogen bond. The differences between molecules relate to the dihedral angles between the rings which range from 2.92 (19) to 26.24 (19)°. The geometry-optimized structure [B3LYP level of theory and 6–311 g+(d,p) basis set] has the same features except that the entire molecule is planar. In the crystal, the three-dimensional architecture is consolidated by a combination of C—H...O, C—H...π, nitro-N—O...π and π–π interactions [inter-centroid distances = 3.649 (2)–3.916 (2) Å].http://scripts.iucr.org/cgi-bin/paper?S1600536814012227crystal structureaminepyridinepolymorphconformation |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Aina Mardia Akhmad Aznan Zanariah Abdullah Vannajan Sanghiran Lee Edward R. T. Tiekink |
| spellingShingle |
Aina Mardia Akhmad Aznan Zanariah Abdullah Vannajan Sanghiran Lee Edward R. T. Tiekink Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine Acta Crystallographica Section E crystal structure amine pyridine polymorph conformation |
| author_facet |
Aina Mardia Akhmad Aznan Zanariah Abdullah Vannajan Sanghiran Lee Edward R. T. Tiekink |
| author_sort |
Aina Mardia Akhmad Aznan |
| title |
Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine |
| title_short |
Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine |
| title_full |
Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine |
| title_fullStr |
Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine |
| title_full_unstemmed |
Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine |
| title_sort |
crystal structure of a new monoclinic polymorph of n-(4-methylphenyl)-3-nitropyridin-2-amine |
| publisher |
International Union of Crystallography |
| series |
Acta Crystallographica Section E |
| issn |
1600-5368 |
| publishDate |
2014-08-01 |
| description |
The title compound, C12H11N3O2, is a second monoclinic polymorph (P21, with Z′ = 4) of the previously reported monoclinic (P21/c, with Z′ = 2) form [Akhmad Aznan et al. (2010). Acta Cryst. E66, o2400]. Four independent molecules comprise the asymmetric unit, which have the common features of a syn disposition of the pyridine N atom and the toluene ring, and an intramolecular amine–nitro N—H...O hydrogen bond. The differences between molecules relate to the dihedral angles between the rings which range from 2.92 (19) to 26.24 (19)°. The geometry-optimized structure [B3LYP level of theory and 6–311 g+(d,p) basis set] has the same features except that the entire molecule is planar. In the crystal, the three-dimensional architecture is consolidated by a combination of C—H...O, C—H...π, nitro-N—O...π and π–π interactions [inter-centroid distances = 3.649 (2)–3.916 (2) Å]. |
| topic |
crystal structure amine pyridine polymorph conformation |
| url |
http://scripts.iucr.org/cgi-bin/paper?S1600536814012227 |
| work_keys_str_mv |
AT ainamardiaakhmadaznan crystalstructureofanewmonoclinicpolymorphofn4methylphenyl3nitropyridin2amine AT zanariahabdullah crystalstructureofanewmonoclinicpolymorphofn4methylphenyl3nitropyridin2amine AT vannajansanghiranlee crystalstructureofanewmonoclinicpolymorphofn4methylphenyl3nitropyridin2amine AT edwardrttiekink crystalstructureofanewmonoclinicpolymorphofn4methylphenyl3nitropyridin2amine |
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