(1-Phenyl­sulfonyl-1H-indol-2-yl)(thio­phen-2-yl)methanone

C KamalaKumar; V Dhayalan; A K Mohanakrishnan; V Balasubramanian; V Manivannan

doi:10.1107/S1600536811005666

. 2011 Feb 26;67(Pt 3):o741. doi: 10.1107/S1600536811005666

(1-Phenylsulfonyl-1H-indol-2-yl)(thiophen-2-yl)methanone

C KamalaKumar ^a, V Dhayalan ^b, A K Mohanakrishnan ^b, V Balasubramanian ^a, V Manivannan ^c,^*

PMCID: PMC3052024 PMID: 21522480

Abstract

The crystal studied of the title compound, C₁₉H₁₃NO₃S₂, was found to be a non-merohedral twin with a domain ratio of 0.877 (3):0.123 (3). There are two independent molecules in the asymmetric unit. The dihedral angles between the mean plane of the indole ring system and the phenylsulfonyl ring are 71.67 (13) and 71.95 (13)° in the two molecules 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 interactions.

Related literature

For biological activity of chromenopyrrole, see: Ma et al. (2001 ▶); Zhao et al. (2002 ▶); Zhou et al. (2006 ▶); Rajeswaran et al. (1999 ▶); For related structures, see: Chakkaravarthi et al. (2007 ▶); Gunasekaran et al. (2009 ▶); Saravanan et al. (2010 ▶).

Experimental

Crystal data

C₁₉H₁₃NO₃S₂
M _r = 367.42
Triclinic,
a = 9.3605 (5) Å
b = 10.8455 (5) Å
c = 17.5482 (9) Å
α = 88.716 (3)°
β = 80.425 (2)°
γ = 71.467 (2)°
V = 1664.68 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 295 K
0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.924, T _max = 0.951
36289 measured reflections
8039 independent reflections
6195 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.077
wR(F ²) = 0.245
S = 1.07
8039 reflections
453 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005666/bt5452sup1.cif

e-67-0o741-sup1.cif^{(28.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005666/bt5452Isup2.hkl

e-67-0o741-Isup2.hkl^{(1.7MB, hkl)}

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

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

Cg is the centroid of the C20–C25 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cg8ⁱ	0.93	2.88	3.693 (6)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

CK thanks AMET University management for their kind support.

supplementary crystallographic information

Comment

Indole derivatives are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001; Zhou et al., 2006; Zhao et al., 2002). In addition, Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure(Chakkaravarthi et al., 2007; Gunasekaran et al., 2009; Saravanan et al., 2010). The compound is non-merohedrally twinned, the suggested transformation matrix is (-1 0 0, 0 - 1 0, -0.664 0.110 1). The dihedral angle between the nine membered indole moiety and the thiophene ring is 54.91 (12) ° for molecule (I) and 56.92 (13) ° for molecule (II) respectively. The torsion angles O1—S1—N1—C1 and O2—S1—N1—C8 in molecule (I), O4—S3—N2—C20 and O5—S3—N2—C27 in molecule (II) [-9.8 (4) ° and 27.7 (4) ° for molecule (I), 9.1 (4) ° and -27.2 (4) ° for molecule (II), respectively] indicates the syn conformation of the sulfonyl moiety.

The sum of bond angles around N1 and N2 are 358.9 (3) ° and 358.6 (3) ° respectively, indicates the sp² hybridization state of atoms N1 and N2. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π [C17—H17···Cg8(1 - x, 1 - y, 1 - z) distance of 3.693 (6)Å (Cg8 is the centroid of the ring defined by the atoms C20—C25)] interactions.

Experimental

To a solution of N-(2-Formylphenyl)benzenesulfonamide (0.5 g, 1.91 mmol) in dry CH3CN (20 ml), K2CO3 (0.8 g, 5.79 mmol), 2-bromo-1-(thiophen-2-yl) ethanone (0.5 g, 2.43 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 x 10 ml) and dried (Na2SO4). Removal of solvent followed by the residue was dissolved in CH3CN (20 ml), Conc.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 x 10 ml) and dried (Na2SO4). Removal of solvent followed by crystallization from methanol afforded the compound as a colorless crystal.