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2-(4-Fluoro-2-nitro-phen-yl)-4-hy-droxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

ABSTRACT: 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-nitro-phenyl ring. It is almost orthogonal to the phenyl-sulfonyl and nitro-phenyl rings, making dihedral angles of 88.45?(8) and 79.26?(7)°, respectively. The mol-ecular structure is stabilized by O-H?O and C-H?O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, mol-ecules 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 supra-molecular R 4 (3)(28) graph-set ring motifs enclosed within these networks.

SUBMITTER: Gopinath S

PROVIDER: S-EPMC3998398 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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2-(4-Fluoro-2-nitro-phen-yl)-4-hy-droxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

Gopinath S S Sethusankar K K Saravanan Velu V Mohanakrishnan Arasambattu K AK

Acta crystallographica. Section E, Structure reports online 20140212 Pt 3

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-nitro-phenyl ring. It is almost orthogonal to the phenyl-sulfonyl and nitro-phenyl rings, making dihedral angles of 88.45 (8) and 79.26 (7)°, respectively. The mol-ecular structure is stabilized by O-H⋯O and C-H⋯O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, mol-ecules are linked by two C-H⋯O hydrogen ...[more]

PMID: 24764987

Similar Datasets

2-(4-Chloro-2-nitro-phen-yl)-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

Project description:In the title compound, C25H15ClN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.152?(3)?Å for the C atom to which the 4-chloro-2-nitro-phenyl ring is attached. Its mean plane is almost orthogonal to the phenyl-sulfonyl and nitro-phenyl rings, making dihedral angles of 82.64?(14) and 79.89?(13)°, respectively. The N atom of the nitro group deviates by 0.032?(3)?Å from the benzene ring to which it is attached. The mol-ecular structure features intra-molecular O-H?O and C-H?O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, which generate C(6) and C(9) chains running in the [100] and [010] directions, respectively, forming a two-dimensional network lying parallel to (001). There are also R 4 (3)(28) supra-molecular graph-set ring motifs enclosed within these networks.

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2-(4-Chloro-2-nitro-phen-yl)-4-meth-oxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

Project description:In the sterically hindered title compound, C26H17ClN2O6S, the carbazole ring has a maximum deviation from planarity of 0.067 (4) Å for the C atom connected to the aldehyde group. The carbazole moiety forms a dihedral angle of 72.8 (1)° with the nitro-substituted benzene ring. The O atom of the meth-oxy group deviates by 0.186 (1) Å from the adjacent carbazole moiety. The phenyl-sulfonyl group forms intra-molecular C-H⋯O bonds between sulfone O atoms and the carbazole moiety, resulting in two S(6) rings. In the crystal, the nitrated benzene rings are linked via C-H⋯O inter-actions forming infinite C(7) chains along [100]. The crystal packing is also characterized by C-H⋯π inter-actions, which result in inversion dimers.

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Project description: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-ecular structure is stabilized by C-H⋯O inter-actions which generate two S(6) and one S(7) ring motif. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming R 3 (3)(15) ring motifs, which are further crosslinked by R 3 (2)(19) ring motifs, resulting in (002) layers. The crystal packing also features C-H⋯π inter-actions.

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2-Hy-droxy-7-meth-oxy-9H-carbazole-3-carbaldehyde.

Project description:The title compound, C(14)H(11)NO(3), was isolated from the roots of Clausena wallichii. The carbazole ring system is approx-imately planar (r.m.s. deviation = 0.039 Å) and the dihedral angle between the two benzene rings is 4.63 (7)°. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked into a zigzag network extending parallel to the ac plane by O-H⋯N and N-H⋯O hydrogen bonds.

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Crystal structure of 2-(2,4-di-chloro-phen-yl)-4-hydroxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

Project description:In the title compound, C25H15Cl2NO4S, the di-chloro-phenyl ring is twisted by 68.69 (11)° from the mean plane of the carbazole ring system [r.m.s. deviation = 0.084 (2)°]. The hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) graph-set motif. In the crystal, pairs of C-H⋯Cl hydrogen bonds link mol-ecules into inversion dimers with an R (2) 2(26) motif. Weak C-H⋯O inter-actions further link these dimers into ribbons propagating in [100].

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3-Bromo-methyl-4-meth-oxy-2-(2-nitro-phen-yl)-9-phenyl-sulfonyl-9H-carbazole.

Project description: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 nitro-phenyl group. The carbazole moiety is almost orthogonal to the benzene rings of the adjacent phenyl-sulfonyl and nitro-phenyl groups, making dihedral angles of 85.43 (15) and 88.62 (12)°, respectively. The mol-ecular conformation is stabilized by two C-H⋯O hydrogen bonds involving the sulfone group, which form similar six-membered rings. In the crystal, mol-ecules 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 inter-actions.

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2-(4,5-Dimeth-oxy-2-nitro-phen-yl)-4-meth-oxy-3-methyl-9-phenyl-sulfonyl-9H-carbazole.

Project description: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, forming two cyclic S(6) motifs. In the crystal, mol-ecules are linked along the a axis in bands consisting of cyclic R 3 (3)(15) motifs through two further C-H⋯O hydrogen bonds.

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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).

Project description: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.

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3-(3-Chloro-2-hy-droxy-phen-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde.

Project description:In the title compound, C(16)H(11)ClN(2)O(2), the pyrazole ring makes dihedral angles of 11.88?(13) and 22.33?(13)° with the 3-chloro-2-hy-droxy-benzene group and phenyl rings, respectively. The phenolic hy-droxy group forms an intra-molecular O-H?N hydrogen bond with the imine N atom of the pyrazole unit. The formyl group is virtually coplanar with the pyrazole ring [dihedral angle = 4.5?(19)°] and acts as an acceptor in an intra-molecular C-H?O hydrogen bond closing seven-membered ring. In the crystal, adjacent mol-ecules are linked through C-H?O hydrogen bonds into infinite chains along the b axis.

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Crystal structure of ethyl 2-phenyl-9-phenyl-sulfonyl-9H-carbazole-3-carboxyl-ate.

Project description:In the title compound, C27H21NO4S, the dihedral angles between the carbazole ring system (r.m.s. deviation = 0.015 Å) and the sulfur-bonded and directly linked benzene rings are 79.98 (11) and 53.51 (18)°, respectively. The benzene rings subtend a dihedral angle of 48.4 (2)°. The ethyl side chain of the ester group has an extended conformation [C-O-C-C = -172.3 (3)°]. In the crystal, inversion dimers linked by pairs of weak C-H⋯O hydrogen bonds generate R 2 (2)(22) loops. The dimers are linked by weak C-H⋯π and π-π [centroid-to-centroid distances ranging from 3.5042 (14) to 3.888 (2) Å] inter-actions, thereby forming a three-dimensional supra-molecular network.

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