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

Umadevi M, Saravanan V, Yamuna R, Mohanakrishnan AK, Chakkaravarthi G - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The carbonyl-bound phenyl ring forms a dihedral angle of 57.32 (5)° with the indole ring system.The two phenyl rings are inclined at 52.68 (7)°.The S atom has a distorted tetra-hedral configuration.

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Affiliation: Research and Development Centre, Bharathiyar University, Coimbatore 641 046, India ; Department of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, India.

ABSTRACT
In the title compound, C22H17NO3S, the sulfonyl-bound phenyl ring is almost orthogonal to the indole ring system, making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at 52.68 (7)°. The S atom has a distorted tetra-hedral configuration. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a helical chain along the b-axis direction.

No MeSH data available.


The mol­ecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
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fig1: The mol­ecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Mentions: The mol­ecular structure of the title compound is shown in Fig. 1 ▸. The sulfonyl-bound phenyl ring (C1–C6) is almost orthogonal to the indole ring system (N1/C7–C14), making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring (C17–C22) forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at an angle of 52.68 (7)°. Atom S1 has a distorted tetra­hedral configuration with angles O1—S1—O2 [119.97 (10)°] and N1—S1—C1 [104.99 (8)°] differing from the ideal tetra­hedral value. As a result of the electron-withdrawing character of the phenyl­sulfonyl group, the bond lengths N1—C7 [1.420 (2) Å] and N1—C14 [1.419 (2) Å] are longer than the mean value of 1.355 (14) Å (Allen et al., 1987 ▸). The geometric parameters of (I) agree well with those in similar reported structures (Chakkaravarthi et al., 2008 ▸, 2009 ▸).


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

Umadevi M, Saravanan V, Yamuna R, Mohanakrishnan AK, Chakkaravarthi G - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4384539&req=5

fig1: The mol­ecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Mentions: The mol­ecular structure of the title compound is shown in Fig. 1 ▸. The sulfonyl-bound phenyl ring (C1–C6) is almost orthogonal to the indole ring system (N1/C7–C14), making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring (C17–C22) forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at an angle of 52.68 (7)°. Atom S1 has a distorted tetra­hedral configuration with angles O1—S1—O2 [119.97 (10)°] and N1—S1—C1 [104.99 (8)°] differing from the ideal tetra­hedral value. As a result of the electron-withdrawing character of the phenyl­sulfonyl group, the bond lengths N1—C7 [1.420 (2) Å] and N1—C14 [1.419 (2) Å] are longer than the mean value of 1.355 (14) Å (Allen et al., 1987 ▸). The geometric parameters of (I) agree well with those in similar reported structures (Chakkaravarthi et al., 2008 ▸, 2009 ▸).

Bottom Line: The carbonyl-bound phenyl ring forms a dihedral angle of 57.32 (5)° with the indole ring system.The two phenyl rings are inclined at 52.68 (7)°.The S atom has a distorted tetra-hedral configuration.

View Article: PubMed Central - HTML - PubMed

Affiliation: Research and Development Centre, Bharathiyar University, Coimbatore 641 046, India ; Department of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, India.

ABSTRACT
In the title compound, C22H17NO3S, the sulfonyl-bound phenyl ring is almost orthogonal to the indole ring system, making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at 52.68 (7)°. The S atom has a distorted tetra-hedral configuration. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a helical chain along the b-axis direction.

No MeSH data available.