2-Methyl-1-phenyl­sulfonyl-1H-indole-3-carbaldehyde

C Ramathilagam; V Saravanan; A K Mohanakrishnan; P R Umarani; V Manivannan

doi:10.1107/S1600536811035665

. 2011 Sep 14;67(Pt 10):o2614. doi: 10.1107/S1600536811035665

2-Methyl-1-phenylsulfonyl-1H-indole-3-carbaldehyde

C Ramathilagam ^a, V Saravanan ^b, A K Mohanakrishnan ^b, P R Umarani ^c, V Manivannan ^d,^*

PMCID: PMC3201221 PMID: 22058759

Abstract

In the title compound, C₁₆H₁₃NO₃S, the sulfonyl-bound phenyl ring forms a dihedral angle of 84.17 (6)° with the indole ring system. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure exhibits weak intermolecular C—H⋯O hydrogen bonds and π–π interactions between the five- and six-membered rings of the indole group [centroid–centroid distance = 3.6871 (9) Å].

Related literature

For the biological activities of indole compounds, see: Chai et al. (2006 ▶); Singh et al. (2000 ▶); Andreani et al. (2001 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶); Ramathilagam et al. (2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₃NO₃S
M _r = 299.33
Monoclinic,
a = 11.6305 (5) Å
b = 8.4039 (4) Å
c = 14.3128 (8) Å
β = 93.126 (1)°
V = 1396.87 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.949, T _max = 0.958
18442 measured reflections
4242 independent reflections
3212 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.116
S = 1.06
4242 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 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 datablock(s) global, I. DOI: 10.1107/S1600536811035665/ci5199sup1.cif

e-67-o2614-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035665/ci5199Isup2.hkl

e-67-o2614-Isup2.hkl^{(203.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811035665/ci5199Isup3.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
C5—H5⋯O1	0.93	2.28	2.8723 (19)	121
C12—H12⋯O3ⁱ	0.93	2.48	3.1664 (19)	131
C16—H16⋯O2ⁱⁱ	0.93	2.48	3.388 (2)	167

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

CR wishes to acknowledge AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Indole derivatives are found in many natural products and these derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). In addition, certain indole derivatives exhibit anti-hepatitis B virus (Chai et al., 2006) activity.

The geometric parameters of the title molecule (Fig. 1) agree well with those observed in related structures (Chakkaravarthi et al., 2007, 2008; Ramathilagam et al., 2011). The dihedral angle between the benzene (C1–C6) and phenyl rings (C11–C16) is 83.81 (7)°. The sum of bond angles around N1 [359.9°] indicates sp² hybridization.

The molecular structure is stabilized by a weak intramolecular C—H···O hydrogen bond and the crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds. The intramolecular C5—H5···O1 hydrogen bond generates an S(6) ring (Bernstein et al., 1995).

Experimental

2-Methylindole-3-carboxaldehyde (5 g, 31.4 mmol) was dissolved in distilled benzene (100 ml). To this benzenesulfonylchloride (6.6 g, 4.8 ml, 37.7 mmol) and 60% aqueous NAOH (32g in 53ml) were added along with tetrabutyl ammonium hydrogensulfate (1.0 g). This two phase system was stirred at room temperature for 2h. It was then diluted with water (200 ml) and the organic layer was separated. The aqueous layer was extracted with benzene (2× 30 ml) and the combined organic extracts were dried (Na₂SO₄). The solvent was removed completely and the crude product was recrystallized from methanol (m.p 431–433 K).