Crystal structure of (E)-2-(4-meth­oxy­styr­yl)-3-methyl-1-phenyl­sulfonyl-1H-indole

M Umadevi; P Raju; R Yamuna; A K Mohanakrishnan; G Chakkaravarthi

doi:10.1107/S2056989015016631

. 2015 Sep 12;71(Pt 10):o723–o724. doi: 10.1107/S2056989015016631

Crystal structure of (E)-2-(4-methoxystyryl)-3-methyl-1-phenylsulfonyl-1H-indole

M Umadevi ^a,^b, P Raju ^c, R Yamuna ^d,^*, A K Mohanakrishnan ^c, G Chakkaravarthi ^e,^*

PMCID: PMC4647445 PMID: 26594443

Abstract

In the title compound, C₂₄H₂₁NO₃S, the dihedral angles between the indole ring system (r.m.s. deviation = 0.030 Å) and the sulfur and ethylene-bonded benzene rings are 80.2 (2) and 49.29 (15)°, respectively. The dihedral angle between the pendant benzene rings is 37.7 (2)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and weak C—H⋯π and π–π [centroid-to-centroid distances = 3.549 (2) and 3.743 (3) Å] interactions, forming a three-dimensional network.

Keywords: crystal structure, phenylsulfonyl, 1H-indole, hydrogen bonding, C—H⋯π interactions, π–π interactions

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ▸); Kolocouris et al. (1994 ▸). For the structures of related compounds, see: Chakkaravarthi et al. (2007 ▸, 2008 ▸).

Experimental

Crystal data

C₂₄H₂₁NO₃S
M _r = 403.48
Monoclinic,
a = 27.373 (4) Å
b = 12.7232 (16) Å
c = 12.0881 (13) Å
β = 102.827 (6)°
V = 4104.9 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T _min = 0.951, T _max = 0.964
26597 measured reflections
4852 independent reflections
2432 reflections with I > 2σ(I)
R _int = 0.120

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.231
S = 1.00
4852 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.28 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 and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015016631/hb7496sup1.cif

e-71-0o723-sup1.cif^{(29.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016631/hb7496Isup2.hkl

e-71-0o723-Isup2.hkl^{(232.9KB, hkl)}

Click here for additional data file.^{(7.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015016631/hb7496Isup3.cml

Click here for additional data file.^{(1MB, tif)}

. DOI: 10.1107/S2056989015016631/hb7496fig1.tif

The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.^{(2.3MB, tif)}

b . DOI: 10.1107/S2056989015016631/hb7496fig2.tif

The crystal packing of the title compound viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1), and C-bound H atoms have been omitted for clarity.

CCDC reference: 1422542

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg2, Cg3 and Cg4 are the centroids of the C1C6, C7C12 and C18C23 rings, respectively.

DHA	DH	HA	D A	DHA
C6H6O2ⁱ	0.93	2.46	3.249(5)	143
C15H15C Cg4ⁱⁱ	0.96	2.82	3.759(4)	167
C24H24A Cg3ⁱⁱⁱ	0.96	2.84	3.634(6)	140
C24H24C Cg2ⁱⁱⁱ	0.96	2.88	3.520(5)	125

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

Acknowledgments

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

S1. Comment

Indole derivatives exhibit antitumour (Andreani et al., 2001) and antiviral (Kolocouris et al., 1994) activities. The molecular structure of the title compound is illustrated in Fig. 1. The geometric parameters of the title molecule agree well with the reported similar structures (Chakkaravarthi et al. 2007, 2008). The torsion angles O1—S1—N1—C7 and O2—S1—N1—C14 [-48.0 (3)° and 38.3 (3)°, respectively] indicate the syn-conformation of the sulfonyl moiety.

In the crystal, the molecules are linked by C—H···O hydrogen bonds (Table 1 & Fig. 2) and the packing also features weak C—H···π (Table 1) and π–π [Cg1···Cg1ⁱ distance 3.549 (2) Å; Cg2···Cg2ⁱⁱ distance 3.743 (3) Å; (i) 1/2 - x,1/2 - y,1 - z; 1 - x,-y,1 - z; Cg1 and Cg2 are the centroids of the rings (N1/C7/C12/C13/C14) and (C1—C6), respectively] interactions in a three-dimensional network.

S2. Experimental

To a suspension of sodium hydride (0.22 g, 4.74 mmol) in dry THF (10 ml) at -10°C, the solution of diethyl (3-methyl-1-(phenylsulfonyl)-1H-indol-2-yl)methylphosphonate (1 g, 2.37 mmol) in dry THF (10 ml) was slowly added under nitrogen atmosphere and stirred for 1 h at -10°C. Then, the solution of p-anisaldehyde (0.31 ml, 2.61 mmol) in dry THF (5 ml) was added and the stirring was continued at -10 to 0°C for another 2 h. After completion of the reaction (monitored by TLC), the yellow solution was poured over crushed ice (80 g) containing Conc. HCl (5 ml). The solid obtained was filtered, dried and recrystallized from methanol solution to afford the title compound in the form of colourless blocks.