Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3)
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چکیده
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⋯π and π-π 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⋯π inter-actions, forming corrugated sheets parallel to the ab plane.
منابع مشابه
Crystal structures of two new carbazole derivatives: 12-(4-nitrophenyl)-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole and 2-methyl-4-(4-nitrophenyl)-9-phenylsulfonyl-9H-thieno[2,3-b]carbazole
The title compounds, C30H18N2O5S, (I), and C27H18N2O4S2, (II), are carbazole derivatives with a phenyl-sulfonyl group and a nitro-phenyl group attached to the carbazole moiety in identical positions in both mol-ecules. A benzo-furan ring system in (I) and a methyl-thio-phene ring in (II) are fused with the respective carbazole moieties on the same sides. The mean plane of the carbazole ring sys...
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In the title compound, C28H24N2O7S, the carbazole system is essentially planar, with a maximum deviation of 0.0644 (19) Å for the C atom connected to the 4,5-dimeth-oxy-2-nitro-phenyl group. The dihedral angle between the carbazole moiety and the dimethoxy-substituted nitrophenyl ring is 58.55 (7)°. The sulfonyl group forms two intra-molecular C-H⋯O bonds with the adjacent carbazole system, for...
متن کامل2-(4,5-Dimethoxy-2-nitrophenyl)-4-methoxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde
In the title compound, C28H22N2O8S, the carbazole ring system is roughly planar, with a maximum deviation of 0.084 (3) Å for the C atom connected to the 4,5-dimeth-oxy-2-nitro-phenyl ring. The dihedral angle between the carbazole system and the dimeth-oxy-substituted nitro-phenyl ring is 57.05 (10)°. The aldehyde C atom deviates by 0.164 (5) Å from its attached carbazole ring system. The mol-ec...
متن کامل6-Methoxy-9-phenylsulfonyl-2-(2-thienyl)-9H-thieno[2,3-b]carbazole
In the title compound, C(25)H(17)NO(3)S(3), the mean planes of the thieno[2,3-b]carbazole and phenyl rings are inclined at an angle of 63.6 (1)°. The mol-ecular structure features short intra-molecular C-H⋯O contacts and the crystal packing exhibits weak inter-molecular C-H⋯S and π-π inter-actions [centroid-to-centroid distances 3.734 (2)-3.888 (2) Å].
متن کامل7-Phenylsulfonyl-7H-benzofurano[2,3-b]carbazole
In the title compound, C(24)H(15)NO(3)S, the dihedral angle between the phenyl ring and the carbozole system is 74.91 (6)°. The S atom exhibits a distorted tetra-hedral geometry [N-S-C = 104.85 (8)°; O-S-O = 119.59 (9)°]. The crystal structure is established by weak inter-molecular π-π inter-actions [centroid-centroid distances = 3.583 (2)-3.782 (2) Å].
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