(3-Phenyl­sulfanyl-1-phenyl­sulfonyl-1H-indol-2-yl)methyl acetate

Alagappa Rammohan; E Govindan; A SubbiahPandi; R Sureshbabu; A K Mohana Krishnan

doi:10.1107/S1600536811014802

. 2011 Apr 29;67(Pt 5):o1240–o1241. doi: 10.1107/S1600536811014802

(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl acetate

Alagappa Rammohan ^a, E Govindan ^a, A SubbiahPandi ^a,^*, R Sureshbabu ^b, A K Mohana Krishnan ^b

PMCID: PMC3089099 PMID: 21754534

Abstract

In the title compound, C₂₃H₁₉NO₄S₂, the indole ring system makes dihedral angles of 89.6 (1) and 84.5 (8)° with the phenylsulfonyl and phenylsulfanyl rings, respectively. In the crystal, the molecules are linked into C(10) chains running along the c axis by an intermolecular C—H⋯O hydrogen bond. In addition, the crystal packing is stabilized by C—H⋯π interactions.

Related literature

For biological activities of indole derivatives, see: Singh et al. (2000 ▶); Andreani et al. (2001 ▶); Quetin-Leclercq (1994 ▶); Mukhopadhyay et al. (1981 ▶); Taylor et al. (1999 ▶); Williams et al. (1993 ▶); Sivaraman et al. (1996 ▶). For related structures, see: Ravishankar et al. (2005 ▶); Chakkaravarthi et al. (2008 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₃H₁₉NO₄S₂
M _r = 437.51
Monoclinic,
a = 14.6530 (6) Å
b = 9.4482 (4) Å
c = 15.2461 (7) Å
β = 97.055 (3)°
V = 2094.76 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.29 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 = 0.981, T _max = 0.985
19397 measured reflections
5235 independent reflections
3638 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.104
S = 1.03
5235 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014802/bt5514sup1.cif

e-67-o1240-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014802/bt5514Isup2.hkl

e-67-o1240-Isup2.hkl^{(251.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811014802/bt5514Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4ⁱ	0.93	2.59	3.274 (2)	131
C15—H15⋯Cg1ⁱⁱ	0.93	2.77	3.559 (2)	143
C16—H16⋯Cg2ⁱⁱ	0.93	2.72	3.5146 (19)	143

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

Acknowledgments

EG and ASP thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for the X-ray intensity data collection.

supplementary crystallographic information

Comment

Indole derivatives have been found to exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole alkaloids extracted from plants possess interesting cytotoxic, antitumour or antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981). Pyrido[1,2-a]indole derivatives have been identified as potent inhibitors of human immunodeficiency virus type 1 (Taylor et al., 1999), and 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide is reported to be a highly potent non-nucleoside inhibitor of HIV-1 reverse transcriptase (Williams et al.,1993). The interaction of phenylsulfonylindole with calf thymus DNA has also been studied by spectroscopic methods (Sivaraman et al., 1996). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, X-ray studies of the title compound (I) have been carried out.

X-Ray analysis confirms the molecular structure and atom connectivity for (I), as illustrated in Fig. 1. The indole ring system is essentially planar, with maximum deviation of 0.020 (2) Å for atom N1. The mean planes of the indole ring system make a dihedral algles of 89.6 (1) and 84.5 (8)° with respect to the phenyl rings, it shows that both the phenyl rings are perpendicular with respect to the indole ring system. The S—O, S—C, and S—N distances are 1.420 (12), 1.754 (17) and 1.676 (14) Å, respectively, these are comparable as observed in similar structures (Ravishankar et al., 2005). As a result of the electron-withdrawing character of the phenylsulfonyl group, the N—Csp² bond lengths, viz. N1—C1 [1.422 (2) Å] and N1—C8 [1.418 (2) Å], are longer than the mean value of 1.355 (14) Å reported for N atoms with planar configurations.

The S atom exhibits significant deviation from that of a regular tetrahedron, with the largest deviations being seen for the O—S—O [O1—S1—O2 120.3 (7)°] and O—S—N angles [O1—S1—N1 105.4 (7)°]. The widening of the angles may be due to repulsive interactions between the two short S═O bonds, similar to what is observed in related structures (Chakkaravarthi et al., 2008). The atom C4 act as a donor to the atom O4 of the neighbouring molecule at (x, 3/2 - y, 1/2 + z). This hydrogen bond is involved in a motif C(10) chain along b axis. In addition to van der Waals interaction, the crystal packing is stabilized by C—H..O and C—H···π interactions.

Experimental

To solution of 2-(bromomethyl)-1-(phenyl sulfonyl)-3-(phenylthio)-1H-indole (2.18 mmol) in dry dimethyl formamide (10 ml), potassium acetate (4.36 mmol) was added under nitrogen atmosphere, the reaction mixture was stirred at room temperature for 5 h, then it was poured over crushed ice (50 g) containing 1 ml of concentrated hydrochloric acid. The obtained brown solid was filtered and dried. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution in methanol.