Phen­yl(3-methyl-1-phenyl­sulfonyl-1H-indol-2-yl)methanone

S Ranjith; A SubbiahPandi; V Dhayalan; A K MohanaKrishnan

doi:10.1107/S1600536811014826

. 2011 Apr 29;67(Pt 5):o1242. doi: 10.1107/S1600536811014826

Phenyl(3-methyl-1-phenylsulfonyl-1H-indol-2-yl)methanone

S Ranjith ^a, A SubbiahPandi ^a,^*, V Dhayalan ^b, A K MohanaKrishnan ^b

PMCID: PMC3089169 PMID: 21754535

Abstract

In the title compound, C₂₂H₁₇NO₃S, 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 tetrahedral. As a result of the electron-withdrawing character of the phenylsulfonyl groups, the N—Csp ² bond lengths are longer than the typical mean value for N atoms with a planar configuration.

Related literature

For background to the biological activity of indole-containing compounds, see: Ma et al. (2001 ▶). For a related structure, see: Ranjith et al. (2011 ▶). For discussion of bond angles around N atoms, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C₂₂H₁₇NO₃S
M _r = 375.43
Monoclinic,
a = 22.8120 (7) Å
b = 10.5199 (4) Å
c = 16.1346 (6) Å
β = 103.926 (1)°
V = 3758.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.953, T _max = 0.964
24166 measured reflections
5682 independent reflections
3487 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.145
S = 1.02
5682 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014826/nk2097sup1.cif

e-67-o1242-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014826/nk2097Isup2.hkl

e-67-o1242-Isup2.hkl^{(272.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811014826/nk2097Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.45	3.025 (2)	120
C15—H15⋯N1	0.93	2.61	3.254 (2)	127
C21—H21⋯O1	0.93	2.53	2.904 (2)	104
C21—H21⋯O2ⁱ	0.93	2.29	3.127 (2)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

SR and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

The indole ring system is present in a number of natural products, many of which are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001). Sulfonamide derivates are well known drugs and are used to control diseases caused by bacterial infections. Against this background and in order to obtain detailed information on molecular conformations in the solid state, X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The indole ring system is essentially planar with a mean deviation from a plane defined by the nine non-H ring atoms of 0.031 (3) Å for N. The sum of bond angles around N1 [348.4 (12)°] of the pyrrole ring is in accordance with sp³ hybridization (Beddoes et al., 1986). The indole ring system makes dihedral angles of 61.7 (8) and 77.7 (8)°, respectively, with the benzene and phenyl rings.

The S—O, S—C, and S—N distances are 1.425 (2), 1.748 (2) and 1.670 (1) Å, respectively and these values are comparable as observed in similar structures (Ranjith et al., 2011). As a result of the electron-withdrawing character of the phenylsulfonyl groups, the N—Csp² bond lengths, viz. N1—C1 [1.420 (2) Å] and N1—C8 [1.422 (2) Å] are longer than the mean value of 1.355 (1) Å reported for N atoms with planar configurations (Ranjith et al., 2011).

Experimental

To a solution of N-(2-acetylphenyl)benzenesulfonamide (0.4 g, 1.45 mmol) in dry CH₃CN (20 ml), K₂CO₃ (0.6 g, 4.34 mmol), 2-bromo-1-phenylethanone (0.34 g, 1.70 mmol) were added. The reaction mixture was stirred at room temperature for 6 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice–water (50 ml), extracted with chloroform (3 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by the residue was dissolved in CH₃CN (20 ml), Concentrated HCl (3 ml) was added. The reaction mixture was then refluxed for 2 h. It was then poured over ice–water (50 ml), extracted with CHCl₃ (3 × 10 ml) and dried (Na₂SO₄). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.