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In the title compound, C25H15FN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.1534 (16) Å for the C atom connected to the 4-fluoro-2-nitro­phenyl ring. It is almost orthogonal to the phenyl­sulfonyl and nitro­phenyl rings, making dihedral angles of 88.45 (8) and 79.26 (7)°, respectively. The mol­ecular structure is stabilized by O—H...O and C—H...O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, mol­ecules are linked by two C—H...O hydrogen bonds, which generate C(6) and C(9) chains running in the [100] and [010] directions, respectively, so forming a two-dimensional network lying parallel to (001). There are also supra­molecular R43(28) graph-set ring motifs enclosed within these networks.

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In the title compound, C26H19BrN2O5S, the carbazole tricycle is essentially planar, with the largest deviation being 0.126 (3) Å for the C atom connected to the nitro­phenyl group. The carbazole moiety is almost orthogonal to the benzene rings of the adjacent phenyl­sulfonyl and nitro­phenyl groups, making dihedral angles of 85.43 (15) and 88.62 (12)°, respectively. The mol­ecular conformation is stabilized by two C—H...O hydrogen bonds involving the sulfone group, which form similar six-membered rings. In the crystal, mol­ecules symmetrically related by a glide plane are linked in C(6) chains parallel to [001] by C—H...O hydrogen bonds formed with the participation of the nitro group. The chains are reinforced by additional C—H...π inter­actions.

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The asymmetric unit of the title compound, C49H36O6·CHCl3, contains half an organic mol­ecule, the complete mol­ecule being generated by the operation of a crystallographic twofold rotation axis, and half a highly disordered chloro­form mol­ecule. The contribution to the diffraction pattern of the latter was removed using the program SQUEEZE in PLATON [Spek (2009). Acta Cryst. D65, 148–155]; the unit-cell characteristics take into account the presence of CHCl3. The dihedral angles between the planes of the naphthalene ring system and the meth­oxy­benzene rings are 71.05 (7) (syn to the central C=O group) and 57.27 (6)° (anti to the central C=O group). In the crystal, mol­ecules are linked by C—H...O inter­actions, generating C(12) chains running parallel to the b axis.
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