Crystal Structure, Spectral Studies, and Hirshfeld Surfaces Analysis of 5-Methyl-5 H -dibenzo[ b , f ]azepine and 5-(4-Methylbenzyl)-5 H -dibenzo[ b , f ]azepine

Abstract

The compounds, 5-methyl-5 H -dibenzo[ b , f ]azepine ( 1 ) and 5-(4-methylbenzyl)-5 H -dibenzo[ b , f ]azepine ( 2 ), were synthesized and characterized by spectral studies, and finally confirmed by single crystal X-ray diffraction method. The compound 1 crystallizes in the orthorhombic crystal system in Pca2 1 space group, having cell parameters a = 11.5681 (18) Å, b = 11.8958 (18) Å, c = 8.0342 (13) Å, and Z = 4 and V = 1105.6 (3) Å 3 . And the compound 2 crystallizes in the orthorhombic crystal system and space group Pbca , with cell parameters a = 16.5858 (5) Å, b = 8.4947 (2) Å, c = 23.1733 (7) Å, and Z = 8 and V = 3264.92 (16) Å 3 . The azepine ring of both molecules 1 and 2 adopts boat conformation with nitrogen atom showing maximum deviations of 0.483 (2) Å and 0.5025 (10) Å, respectively. The C–H ⋯ π short contacts were observed. The dihedral angle between fused benzene rings to the azepine motif is 47.1 (2)° for compound 1 and 52.59 (6)° for compound 2 , respectively. The short contacts were analyzed and Hirshfeld surfaces computational method for both molecules revealed that the major contribution is from C ⋯ H and H ⋯ H intercontacts.