2-(4-Chloro-2-nitrophenyl)-5-[4-(propyloxy)phenyl]-1,3,4-oxadiazole

• Main Authors: Daniel Limbach, Heiner Detert, Dieter Schollmeyer
• Format: Article
• Language: English
• Published: International Union of Crystallography 2016-11-01
• Series: IUCrData
• Subjects: crystal structure; 1,3,4-oxadiazole; nitro compound; hydrogen bonding; C—H...π interactions
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S241431461601782X

The title compound, C17H14ClN3O4, was prepared by the Huisgen reaction of 4-chloro-2-nitrobenzoyl chloride and 5-(4-propyloxyphenyl)tetrazole. The diphenyl-1,3,4-oxadiazole unit is nearly planar. The oxadiazole ring is inclined to the 4-chloro-2-nitrophenyl ring by 7.77 (8)°, and by 7.93 (8)° to the 4-propyloxyphenyl ring. The benzene rings are inclined to one another by 1.32 (7)°. The nitro group is twisted out of the plane of the benzene ring to which it is attached by 73.59 (16)°. The propoxy chain mean plane is inclined to the benzene ring to which it is attached by 4.46 (13)°. In the crystal, C—H...O and C—H...N hydrogen bonds connect the molecules, forming ribbons propagating along the b-axis direction. The ribbons are linked by C—H...π interactions, forming slabs parallel to the ab plane.