Crystal structures of three carbazole derivatives: 12-ethyl-7-phenyl-sulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimeth-oxy-2-nitro-phen-yl)-4-hy-droxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenyl-sulfonyl-7H-benzofuro[2,3-b]carbazole, (3).

ABSTRACT: The three title compounds, C₂₆H₁₉NO₃S, (1), C₂₇H₂₀N₂O₈S, (2), and C₃₀H₁₉NO₃S, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzo-furan moiety fused to a carbazole unit. In (2), a di-meth-oxy-nitro-phenyl ring is attached to the carbazole moiety. In the three derivatives, a phenyl-sulfonyl group is attached to the N atom of the carbazole unit. Compound (1) crystallizes with two independent mol-ecules in the asymmetric unit (A and B). The carbazole skeleton in the three compounds is essentially planar. In compound (1), the benzene ring of the phenyl-sulfonyl moiety is almost orthogonal to the carbazole moiety, with dihedral angles of 85.42?(9) and 84.52?(9)° in mol-ecules A and B, respectively. The benzene ring of the phenyl-sulfonyl group in compounds (2) and (3) are inclined to the carbazole moiety, making dihedral angles of 70.73?(13) and 81.73?(12)°, respectively. The S atom has a distorted tetra-hedral configuration in all three compounds. In the crystals, C-H?O hydrogen bonds give rise to R₂²(12) inversion dimers for compound (1), and to R₂²(24) inversion dimers and R₄⁴(40) ring motifs for compound (2). The crystal packing in (1) also features C-H?? and ?-? inter-actions [shortest inter-centroid distance = 3.684?(1)?Å], leading to supra-molecular three-dimensional aggregation. In the crystal of compound (2), the combination of the various C-H?O hydrogen bonds leads to the formation of a three-dimensional network. In the crystal of compound (3), mol-ecules are linked by C-H?O hydrogen bonds, forming chains running parallel to the a axis, and the chains are linked by C-H?? inter-actions, forming corrugated sheets parallel to the ab plane.

SUBMITTER: Gangadharan R 

PROVIDER: S-EPMC5137599 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature