Abstract
In the title compound, C27H29BrN2, the carbazole ring system is essentially planar, with an r.m.s. deviation of 0.0781 (16) Å. An intra-molecular N-H⋯N hydrogen bond forms an S(6) ring motif. One of the tert-butyl substituents shows rotational disorder over two sites with occupancies of 0.592 (3) and 0.408 (3). In the crystal, two mol-ecules are associated into an inversion dimer through a pair of C-H⋯π inter-actions. The dimers are further linked by another pair of C-H⋯π inter-actions, forming a ribbon along the c-axis direction. A C-H⋯π inter-action involving the minor disordered component and the carbazole ring system links the ribbons, generating a network sheet parallel to (100).
Highlights
In the title compound, C27H29BrN2, the carbazole ring system is essentially planar, with an r.m.s. deviation of 0.0781 (16) A
Two molecules are associated into an inversion dimer through a pair of C—HÁ Á Á interactions
A Schiff base including carbazole, N-(3,6-di-tert-butyl-9H-calbazol-1-ylmethylidene)-4-bromoaniline, is newly synthesized. 3,6-Ditert-butyl-9H-carbazole is useful in order to substitute the 1-position of the 9H-carbazole moiety because the substitution reaction would only occur at its 1- and 8-positions
Summary
Carbazole derivatives have been widely applied in various fields such as pharmaceuticals (Obora, 2018), electroluminescent materials (Krucaite & Grigalevicius, 2019; Taneda, et al, 2015) and dyes (Zhao et al, 2019). As a result of the high acidity of the N—H bond, 9H-carbazoles have attracted much attention as hydrogen donors in hydrogenbonding systems (Rubio et al, 2015; Wiosna-Sałyga et al, 2006). Substitution of the 1 position of 9H-carbazole with a hydrogen acceptor can afford an intramolecular hydrogenbonding system in the molecules. A Schiff base including carbazole, N-(3,6-di-tert-butyl-9H-calbazol-1-ylmethylidene)-4-bromoaniline, is newly synthesized. 3,6-Ditert-butyl-9H-carbazole is useful in order to substitute the 1-position of the 9H-carbazole moiety because the substitution reaction would only occur at its 1- and 8-positions. The title compound has two tert-butyl groups on the carbazole moiety. The title compound is a suitable model to investigate an intramolecular hydrogen bond between the heteroaromatic N—H and the N atom of the imino group. Symmetry codes: (i) Àx; Ày; Àz þ 1; (ii) Àx; Ày; Àz; (iii) x; Ày À 12; z À 12
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