Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.005 Å; R factor = 0.048; wR factor = 0.129; data-to-parameter ratio = 15.9.In the title compound, C 17 H 11 BrFN 3 S, the imidazothiadiazole and bromophenyl rings are individually almost planar, with maximum deviations of 0.0215 (4) and 0.0044 (4) Å , respectively, and are inclined at an angle of 27.34 (3) with respect to each other. The dihedral angle between the mean planes of the fluorobenzyl and imidazothiadiazole rings is 79.54 (3). The crystal structure is stabilized by intermolecular C-HÁ Á ÁN interactions resulting in chains of molecules along the b axis.
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ExperimentalCrystal data
In the title compound, C10H12N2S, one of the C atoms of the cyclohexene ring (at position 6) and the methyl group attached to it are disordered over two sets of sites in a 0.650 (3):0.350 (3) ratio. The cyclohexene ring in both the major and minor occupancy conformers adopts a half-chair conformation. The thiophene ring is essentially planar (r.m.s. deviation = 0.05 Å). In the crystal, N—H⋯N hydrogen bonds involving the amino groups result in inversion dimers with R
2
2(12) graph-set motif. Further N—H⋯N hydrogen bonds involving the amino and carbonitrile groups generate zigzag chains along the a axis.
In the title compound, C18H11BrN4OS, the imidazothiadiazole and benzisoxazole rings are individually planar with maximum deviations of 0.025 (3) 0.015 (4) Å, respectively, and are inclined at an angle of 23.51 (7)° with respect to each other. The planes of the imidazothiadiazole and bromophenyl rings are inclined at an angle of 27.34 (3)°. In the crystal, intermolecular C—H⋯N interactions result in chains of molecules along the b and c axes. Moreover, C—H⋯O interactions result in centrosymmetric head-to-head dimers with R
2
2(24) graph-set motifs. The molecular packing is further stabilized by π–π stacking interactions between the imidazole rings with a shortest centroid–centroid distance of 3.492 (3) Å. In addition, C—H⋯π interactions are observed in the crystal structure.
In the title compound, C
18
H
11
ClN
4
OS, the benzisoxazole and imidazothiadiazole rings are inclined at an angle of 23.81 (7)° with respect to each other. The imidazothiadiazole and chlorophenyl rings make a dihedral angle of 27.34 (3)°. In the crystal, intermolecular C—H⋯N interactions generate a chain along the
c
axis and C—H⋯O interactions form centrosymmetric dimers resulting in an
R
2
2
(26) graph-set motif. Moreover, the C—H⋯N and S⋯N [3.206 (4) Å] interactions links the molecules into
R
(7) ring motifs. The packing is further stabilized by π–π stacking interactions between the thiadiazole rings with a shortest centroid–centroid distance of 3.497 (3) Å. In addition, C—H⋯π interactions are observed in the crystal structure
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