Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide
The title compound, C18H18F2N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit. They differ essentially in the orientation of the pyridine ring with respect to the benzene ring; these two rings are inclined to each other by 53.3 (2)° in molecule A and by 72.9 (2)° in...
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doaj-dab7dbd8f0be41e98c65ae7367648b532020-11-25T02:13:02ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-10-0175101515151810.1107/S2056989019012866su5514Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamideG. Artheswari0V. Maheshwaran1N. Gautham2CAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, IndiaCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, IndiaCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, IndiaThe title compound, C18H18F2N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit. They differ essentially in the orientation of the pyridine ring with respect to the benzene ring; these two rings are inclined to each other by 53.3 (2)° in molecule A and by 72.9 (2)° in molecule B. The 3-(cyclopropylmethoxy) side chain has an extended conformation in both molecules. The two molecules are linked by a pair of C—H...O hydrogen bonds and two C—H...π interactions, forming an A–B unit. In the crystal, this unit is linked by N—H...O hydrogen bonds, forming a zigzag –A–B–A–B– chain along [001]. The chains are linked by C—H...N and C—H...F hydrogen bonds to form layers parallel to the ac plane. Finally, the layers are linked by a third C—H...π interaction, forming a three-dimensional structure. The major contributions to the Hirshfeld surface are those due to H...H contacts (39.7%), followed by F...H/H...F contacts (19.2%).http://scripts.iucr.org/cgi-bin/paper?S2056989019012866crystal structurebenzamidepyridinecyclopropanesupramolecular featureshydrogen bondingC—H...π interactionsHirshfeld surface analysis |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
G. Artheswari V. Maheshwaran N. Gautham |
spellingShingle |
G. Artheswari V. Maheshwaran N. Gautham Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide Acta Crystallographica Section E: Crystallographic Communications crystal structure benzamide pyridine cyclopropane supramolecular features hydrogen bonding C—H...π interactions Hirshfeld surface analysis |
author_facet |
G. Artheswari V. Maheshwaran N. Gautham |
author_sort |
G. Artheswari |
title |
Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide |
title_short |
Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide |
title_full |
Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide |
title_fullStr |
Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide |
title_full_unstemmed |
Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide |
title_sort |
crystal structure and hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-n-(pyridin-2-ylmethyl)benzamide |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2019-10-01 |
description |
The title compound, C18H18F2N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit. They differ essentially in the orientation of the pyridine ring with respect to the benzene ring; these two rings are inclined to each other by 53.3 (2)° in molecule A and by 72.9 (2)° in molecule B. The 3-(cyclopropylmethoxy) side chain has an extended conformation in both molecules. The two molecules are linked by a pair of C—H...O hydrogen bonds and two C—H...π interactions, forming an A–B unit. In the crystal, this unit is linked by N—H...O hydrogen bonds, forming a zigzag –A–B–A–B– chain along [001]. The chains are linked by C—H...N and C—H...F hydrogen bonds to form layers parallel to the ac plane. Finally, the layers are linked by a third C—H...π interaction, forming a three-dimensional structure. The major contributions to the Hirshfeld surface are those due to H...H contacts (39.7%), followed by F...H/H...F contacts (19.2%). |
topic |
crystal structure benzamide pyridine cyclopropane supramolecular features hydrogen bonding C—H...π interactions Hirshfeld surface analysis |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989019012866 |
work_keys_str_mv |
AT gartheswari crystalstructureandhirshfeldsurfaceanalysisof3cyclopropylmethoxy4difluoromethoxynpyridin2ylmethylbenzamide AT vmaheshwaran crystalstructureandhirshfeldsurfaceanalysisof3cyclopropylmethoxy4difluoromethoxynpyridin2ylmethylbenzamide AT ngautham crystalstructureandhirshfeldsurfaceanalysisof3cyclopropylmethoxy4difluoromethoxynpyridin2ylmethylbenzamide |
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1724906692253057024 |