Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.003 Å; R factor = 0.048; wR factor = 0.140; data-to-parameter ratio = 17.6.In the title compound, C 18 H 19 N 3 O 2 , the dihedral angle between the benzene rings is 20.47 (10) and an intramolecular N-HÁ Á ÁO hydrogen bond occurs, generating an S(5) ring. In the crystal, inversion dimers linked by pairs of N-HÁ Á ÁO hydrogen bonds lead to R 2 2 (8) loops.
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ExperimentalCrystal data
In this study, twenty-one arylaminoquinoxalinone derivatives were synthesized and their antibacterial activities against Staphylococci aureus, Pseudomonas aureus, Escherichia coli, Bacillus subtilis, Salmonella typhi, and Shigella pneumoniae were evaluated relative to known antibiotics; augmentin, ampicillin, and chloramphenicol. The insecticidal activities of the prepared compounds were also investigated against Tribolium castaneum using permethrin as a standard insecticide. The derivatives were synthesized using both conventional and microwave techniques. Their structures were confirmed using spectral techniques and elemental analysis.
The title molecule, C8H6BrN, is almost planar (r.m.s. deviation for the non-H atoms = 0.008 Å). In the crystal, weak π–π stacking interactions [centroid–centroid separations = 3.782 (2) and 3.919 (2) Å] generate [100] columns of molecules.
The –SCH2CH2CH2CH2S– portion of the title compound, C12H14N2S2, adopts an extended zigzag conformation. The angles at the tetrahedral carbon atoms are marginally increased [113.63 (12)° and 111.38 (17)° for S—C—C and C—C—C respectively] from the idealized tetrahedral angle. The molecule lies on an inversion center located at the mid-point of the butyl chain. In the crystal, there is a π–π stacking interaction between inversion-related pyrimidine rings with mean interplanar spacing of 3.494 (2) Å.
In the title compound, C13H14N2O3, the fused ring system is almost planar (r.m.s. deviation = 0.015 Å). The r.m.s. deviation for all the non-H atoms of the molecule is 0.065Å. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds generate polymeric chains along the b axis containing alternating centrsymmetric R
2
2(8) and R
2
2(20) loops.
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