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Phen-yl(1-phenyl-sulfonyl-1H-indol-2-yl)methanone.

ABSTRACT: The asymmetric unit of the title compound, C(21)H(15)NO(3)S, contains two crystallographically independent mol-ecules. As a result of the electron-withdrawing character of the phenyl-sulfonyl groups, the N-Csp(2) bond lengths are slightly longer than the anti-cipated value of approximately 1.35 Å for N atoms with planar configurations. Both unique S atoms have a distorted tetra-hedral configuration. In each mol-ecule, the indole ring system is essentially planar (r.m.s. deviations for all non-H atoms of 0.020 and 0.023 Å). In one mol-ecule, the indole ring system makes dihedral angles of 65.7 (8) and 73.4 (8)°, respectively, with the benzene and phenyl rings [62.2 (7) and 72.1 (7)°, respectively, in the other mol-ecule].

SUBMITTER: Ranjith S

PROVIDER: S-EPMC3099964 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Phen-yl(3-methyl-1-phenyl-sulfonyl-1H-indol-2-yl)methanone.

Project description:In the title compound, C(22)H(17)NO(3)S, the N atom of the indole ring system deviates by 0.031?(3)?Å from a least-squares plane fitted through all nine non-H ring atoms. The geometry around the S atom can be described as distorted tetra-hedral. As a result of the electron-withdrawing character of the phenyl-sulfonyl groups, the N-Csp(2) bond lengths are longer than the typical mean value for N atoms with a planar configuration.

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(4-Bromo-phen-yl)(1-phenyl-sulfonyl-1H-indol-2-yl)methanone.

Project description:In the title compound, C(21)H(14)BrNO(3)S, the indole ring system forms dihedral angles of 65.64?(8) and 59.30?(8)°, respectively, with the phenyl and bromo-phenyl rings. In the crystal, mol-ecules are connected by a C-H?O hydrogen bond, forming a chain along [101]. The chains are further connected by weak inter-molecular C-H?? inter-actions, forming a layer parallel to the ac plane.

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(1-Phenyl-sulfonyl-1H-indol-2-yl)(thio-phen-2-yl)methanone.

Project description:The crystal studied of the title compound, C(19)H(13)NO(3)S(2), was found to be a non-merohedral twin with a domain ratio of 0.877 (3):0.123 (3). There are two independent mol-ecules in the asymmetric unit. The dihedral angles between the mean plane of the indole ring system and the phenyl-sulfonyl ring are 71.67 (13) and 71.95 (13)° in the two mol-ecules while the indole unit and the thiophene ring make dihedral angles of 54.91 (12) and 56.92 (13)° in the two molecules. The crystal packing is stabilized by weak C-H⋯π inter-actions.

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(Phen-yl)(1-phenyl-sulfonyl-1H-indol-3-yl)methanone.

Project description:In the title compound, C(21)H(15)NO(3)S, the sulfonyl-bound phenyl ring forms a dihedral angle of 86.28?(5)° with the indole ring system. The mol-ecular structure is stabilized by intra-molecular C-H?O hydrogen bonds. The crystal packing is stabilized by weak inter-molecular C-H?O and C-H?? inter-actions.

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Crystal structure of (2-bromo-methyl-1-phenyl-sulfonyl-1H-indol-3-yl)(phen-yl)methanone.

Project description:In the title compound, C22H16BrNO3S, the phenyl rings make dihedral angles of 84.81 (16) and 61.67 (17)° with the indole ring system (r.m.s. deviation = 0.012 Å), while the phenyl rings are inclined to one another by 69.5 (2)°. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O hydrogen bonds. The sulfonyl S atom has a distorted tetra-hedral configuration. In the crystal, there are no significant inter-molecular inter-actions present.

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(4-Bromo-phen-yl)(1H-indol-7-yl)methanone.

Project description:In the crystal, the mol-ecules of the title compound, C(15)H(10)BrNO, are connected into centrosymmetric dimers by pairs of N-H?O hydrogen bonds. The dihedral angle between the planes of indole ring system and benzene ring is 50.13?(5)°. The indole plane is significantly less twisted from the plane of the central C-C(=O)-C bridge than the benzene plane [dihedral angles = 15.51?(3) and 40.13?(7)°, respectively]. The bond angles within the benzene ring show an approximately additive effect of the influence of both substituents.

| S-EPMC2971073 | biostudies-literature

Crystal structure of (2-methyl-1-phenyl-sulfon-yl-1H-indol-3-yl)(phen-yl)methanone.

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1-{2-[(E)-2-(2-Nitro-phen-yl)ethen-yl]-1-phenyl-sulfonyl-1H-indol-3-yl}ethanone.

Project description:In the title compound, C24H18N2O5S, the S atom has a distorted tetra-hedral configuration, with bond angles varying from 105.11?(7) to 119.98?(8)°. As a result of the electron-withdrawing character of the phenyl-sulfonyl group, the N-Csp (2) bond lengths [1.414?(2) and 1.413?(2)?Å] are slightly longer than the reported value of 1.355?(14)?Å for N atoms with a planar configuration. The indole moiety is essentially planar, with a maximum deviation of 0.0177?(14)?Å for the N atom. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 85.70?(7)° with the mean plane of the indole moiety. The mol-ecular structure features intra-molecular C-H?O hydrogen bonds, which generate S(6) and S(12) ring motifs. In the crystal, adjacent mol-ecules are linked via C-H?O hydrogen bonds, forming infinite C(7) chains running along the a-axis direction. The crystal packing also features C-H?? inter-actions, which form a three-dimensional structure.

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(2-Methyl-1-phenyl-sulfonyl-1H-indol-3-yl)methanol.

Project description:In the title compound, C(16)H(15)NO(3)S, the plane of the phenyl ring forms a dihedral angle of 80.37 (8)° with the indole ring system. The crystal packing is stabilized by weak O-H⋯O hydrogen bonds which link the mol-ecules into infinite chains along the a axis of the crystal.

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(2-Methyl-1-phenyl-sulfonyl-1H-indol-3-yl)phenyl-methyl acetate.

Project description:In the title compound, C(24)H(21)NO(4)S, the indole ring system makes dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the S- and C-bound phenyl rings. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. In the crystal, a weak inter-molecular C-H⋯O hydrogen bond and a C-H⋯π inter-action are also observed.

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