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

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

doi:10.1107/S2056989015016631

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o723-o724

doi:10.1107/S2056989015016631

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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 and G. Chakkaravarthi ^e ^*

^aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, ^bDepartment of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, India, ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^dDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and ^eDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 4 September 2015; accepted 6 September 2015; online 12 September 2015)

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.

CCDC reference: 1422542

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₄H₂₁NO₃S
M_r = 403.48
Monoclinic, C 2/c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C7–C12 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.46	3.249 (5)	143
C15—H15C⋯Cg4ⁱⁱ	0.96	2.82	3.759 (4)	167
C24—H24A⋯Cg3ⁱⁱⁱ	0.96	2.84	3.634 (6)	140
C24—H24C⋯Cg2ⁱⁱⁱ	0.96	2.88	3.520 (5)	125
Symmetry codes: (i) $[x, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z-{\script{1\over 2}}]$ ; (iii) x, y, z+1.

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.

Supporting information

CCDC reference: 1422542

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015016631/hb7496sup1.cif

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. 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.

(E)-2-(4-Methoxystyryl)-3-methyl-1-phenylsulfonyl-1H-indole top

Crystal data top

C₂₄H₂₁NO₃S	F(000) = 1696
M_r = 403.48	D_x = 1.306 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5639 reflections
a = 27.373 (4) Å	θ = 2.6–24.6°
b = 12.7232 (16) Å	µ = 0.18 mm⁻¹
c = 12.0881 (13) Å	T = 295 K
β = 102.827 (6)°	Block, colourless
V = 4104.9 (9) Å³	0.28 × 0.24 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	4852 independent reflections
Radiation source: fine-focus sealed tube	2432 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.120
ω and φ scan	θ_max = 27.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→35
T_min = 0.951, T_max = 0.964	k = −16→16
26597 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.109P)² + 3.4059P] where P = (F_o² + 2F_c²)/3
4852 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₄H₂₁NO₃S	V = 4104.9 (9) Å³
M_r = 403.48	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.373 (4) Å	µ = 0.18 mm⁻¹
b = 12.7232 (16) Å	T = 295 K
c = 12.0881 (13) Å	0.28 × 0.24 × 0.20 mm
β = 102.827 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4852 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2432 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.964	R_int = 0.120
26597 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.00	Δρ_max = 0.28 e Å⁻³
4852 reflections	Δρ_min = −0.37 e Å⁻³
264 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.40832 (12)	0.0851 (3)	0.4987 (3)	0.0558 (9)
C2	0.44297 (16)	0.1492 (3)	0.5659 (4)	0.0830 (12)
H2	0.4371	0.1778	0.6326	0.100*
C3	0.48806 (19)	0.1704 (4)	0.5304 (7)	0.117 (2)
H3	0.5124	0.2133	0.5741	0.140*
C4	0.4957 (2)	0.1274 (5)	0.4313 (7)	0.121 (2)
H4	0.5254	0.1412	0.4083	0.145*
C5	0.4609 (2)	0.0657 (5)	0.3678 (5)	0.1072 (18)
H5	0.4667	0.0369	0.3011	0.129*
C6	0.41692 (15)	0.0444 (3)	0.3994 (3)	0.0697 (10)
H6	0.3928	0.0024	0.3536	0.084*
C7	0.30101 (11)	0.1982 (2)	0.3861 (3)	0.0467 (7)
C8	0.29070 (13)	0.1401 (3)	0.2867 (3)	0.0583 (9)
H8	0.2952	0.0676	0.2882	0.070*
C9	0.27364 (14)	0.1922 (4)	0.1857 (3)	0.0712 (11)
H9	0.2671	0.1542	0.1183	0.085*
C10	0.26607 (15)	0.2987 (4)	0.1820 (3)	0.0748 (11)
H10	0.2537	0.3314	0.1126	0.090*
C11	0.27647 (13)	0.3574 (3)	0.2794 (3)	0.0642 (10)
H11	0.2713	0.4297	0.2761	0.077*
C12	0.29493 (11)	0.3081 (3)	0.3841 (3)	0.0496 (8)
C13	0.31014 (12)	0.3465 (2)	0.4972 (3)	0.0516 (8)
C14	0.32558 (11)	0.2641 (2)	0.5673 (3)	0.0480 (8)
C15	0.30517 (15)	0.4586 (3)	0.5297 (4)	0.0736 (11)
H15A	0.3076	0.4632	0.6100	0.110*
H15B	0.2732	0.4853	0.4902	0.110*
H15C	0.3314	0.4994	0.5097	0.110*
C16	0.34235 (13)	0.2629 (3)	0.6895 (3)	0.0537 (8)
H16	0.3298	0.2110	0.7298	0.064*
C17	0.37458 (13)	0.3316 (3)	0.7474 (3)	0.0556 (8)
H17	0.3887	0.3794	0.7054	0.067*
C18	0.38995 (12)	0.3393 (3)	0.8702 (3)	0.0534 (8)
C19	0.42576 (14)	0.4133 (3)	0.9200 (3)	0.0675 (10)
H19	0.4405	0.4553	0.8736	0.081*
C20	0.43979 (15)	0.4256 (3)	1.0354 (3)	0.0734 (11)
H20	0.4635	0.4762	1.0657	0.088*
C21	0.41924 (13)	0.3642 (3)	1.1070 (3)	0.0619 (9)
C22	0.38457 (12)	0.2888 (3)	1.0604 (3)	0.0589 (9)
H22	0.3707	0.2457	1.1075	0.071*
C23	0.37042 (13)	0.2769 (3)	0.9445 (3)	0.0602 (9)
H23	0.3470	0.2255	0.9148	0.072*
C24	0.4123 (2)	0.3287 (4)	1.2952 (4)	0.1073 (17)
H24A	0.3772	0.3454	1.2805	0.161*
H24B	0.4278	0.3481	1.3717	0.161*
H24C	0.4164	0.2547	1.2852	0.161*
N1	0.31802 (9)	0.16882 (19)	0.5006 (2)	0.0477 (7)
O1	0.32587 (9)	−0.02048 (17)	0.4661 (2)	0.0633 (7)
O2	0.35975 (11)	0.0507 (2)	0.65544 (19)	0.0733 (8)
O3	0.43465 (10)	0.3842 (3)	1.2199 (2)	0.0862 (9)
S1	0.35144 (3)	0.06038 (6)	0.53598 (7)	0.0512 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0529 (19)	0.0443 (19)	0.068 (2)	0.0044 (15)	0.0089 (17)	0.0051 (16)
C2	0.071 (3)	0.058 (3)	0.112 (3)	0.002 (2)	0.005 (2)	−0.013 (2)
C3	0.064 (3)	0.071 (3)	0.204 (7)	−0.011 (2)	0.008 (4)	0.002 (4)
C4	0.082 (4)	0.097 (4)	0.199 (7)	0.008 (3)	0.065 (4)	0.028 (4)
C5	0.088 (3)	0.114 (4)	0.138 (5)	0.007 (3)	0.064 (3)	0.021 (4)
C6	0.066 (2)	0.076 (3)	0.071 (3)	0.0089 (19)	0.0230 (19)	0.004 (2)
C7	0.0452 (17)	0.0462 (19)	0.0502 (19)	0.0007 (14)	0.0141 (14)	0.0035 (15)
C8	0.065 (2)	0.048 (2)	0.061 (2)	−0.0047 (16)	0.0105 (17)	−0.0074 (17)
C9	0.078 (3)	0.081 (3)	0.051 (2)	−0.007 (2)	0.0066 (19)	0.001 (2)
C10	0.079 (3)	0.074 (3)	0.068 (3)	−0.003 (2)	0.009 (2)	0.017 (2)
C11	0.063 (2)	0.053 (2)	0.076 (3)	0.0011 (17)	0.0119 (19)	0.016 (2)
C12	0.0437 (17)	0.0437 (19)	0.063 (2)	0.0011 (14)	0.0156 (15)	0.0046 (16)
C13	0.0476 (18)	0.0409 (19)	0.069 (2)	0.0003 (14)	0.0194 (16)	−0.0030 (17)
C14	0.0498 (18)	0.0418 (18)	0.057 (2)	−0.0044 (14)	0.0227 (15)	−0.0097 (15)
C15	0.075 (3)	0.044 (2)	0.102 (3)	0.0026 (18)	0.021 (2)	−0.008 (2)
C16	0.063 (2)	0.047 (2)	0.057 (2)	−0.0032 (16)	0.0262 (17)	−0.0063 (15)
C17	0.059 (2)	0.053 (2)	0.056 (2)	−0.0041 (16)	0.0173 (16)	−0.0039 (16)
C18	0.0542 (19)	0.046 (2)	0.062 (2)	−0.0012 (15)	0.0176 (16)	−0.0080 (16)
C19	0.074 (2)	0.067 (2)	0.066 (2)	−0.018 (2)	0.026 (2)	−0.0078 (19)
C20	0.068 (2)	0.079 (3)	0.074 (3)	−0.025 (2)	0.018 (2)	−0.019 (2)
C21	0.057 (2)	0.066 (2)	0.062 (2)	0.0018 (18)	0.0109 (18)	−0.0069 (19)
C22	0.057 (2)	0.057 (2)	0.063 (2)	−0.0004 (17)	0.0147 (17)	0.0087 (18)
C23	0.058 (2)	0.050 (2)	0.071 (2)	−0.0051 (16)	0.0119 (18)	−0.0014 (18)
C24	0.148 (5)	0.098 (4)	0.067 (3)	−0.013 (3)	0.005 (3)	0.018 (3)
N1	0.0532 (15)	0.0406 (15)	0.0509 (16)	−0.0033 (12)	0.0149 (12)	−0.0032 (12)
O1	0.0731 (16)	0.0360 (13)	0.0815 (17)	−0.0048 (11)	0.0189 (13)	−0.0054 (11)
O2	0.113 (2)	0.0603 (16)	0.0497 (15)	0.0094 (14)	0.0244 (14)	0.0132 (12)
O3	0.0832 (19)	0.109 (2)	0.0646 (18)	−0.0207 (17)	0.0131 (15)	−0.0117 (16)
S1	0.0654 (6)	0.0367 (5)	0.0536 (5)	0.0005 (4)	0.0176 (4)	0.0033 (4)

Geometric parameters (Å, º) top

C1—C2	1.372 (5)	C14—C16	1.447 (4)
C1—C6	1.375 (5)	C15—H15A	0.9600
C1—S1	1.742 (4)	C15—H15B	0.9600
C2—C3	1.420 (7)	C15—H15C	0.9600
C2—H2	0.9300	C16—C17	1.326 (4)
C3—C4	1.375 (8)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.454 (5)
C4—C5	1.337 (8)	C17—H17	0.9300
C4—H4	0.9300	C18—C23	1.391 (5)
C5—C6	1.369 (6)	C18—C19	1.395 (5)
C5—H5	0.9300	C19—C20	1.372 (5)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.386 (4)	C20—C21	1.376 (5)
C7—C12	1.407 (5)	C20—H20	0.9300
C7—N1	1.409 (4)	C21—O3	1.359 (4)
C8—C9	1.377 (5)	C21—C22	1.379 (5)
C8—H8	0.9300	C22—C23	1.377 (5)
C9—C10	1.370 (6)	C22—H22	0.9300
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.370 (5)	C24—O3	1.396 (5)
C10—H10	0.9300	C24—H24A	0.9600
C11—C12	1.403 (5)	C24—H24B	0.9600
C11—H11	0.9300	C24—H24C	0.9600
C12—C13	1.424 (5)	N1—S1	1.658 (3)
C13—C14	1.355 (4)	O1—S1	1.414 (2)
C13—C15	1.494 (5)	O2—S1	1.416 (2)
C14—N1	1.446 (4)

C2—C1—C6	120.7 (4)	H15A—C15—H15B	109.5
C2—C1—S1	119.6 (3)	C13—C15—H15C	109.5
C6—C1—S1	119.6 (3)	H15A—C15—H15C	109.5
C1—C2—C3	117.8 (5)	H15B—C15—H15C	109.5
C1—C2—H2	121.1	C17—C16—C14	123.7 (3)
C3—C2—H2	121.1	C17—C16—H16	118.2
C4—C3—C2	120.0 (5)	C14—C16—H16	118.2
C4—C3—H3	120.0	C16—C17—C18	126.3 (3)
C2—C3—H3	120.0	C16—C17—H17	116.9
C5—C4—C3	120.4 (5)	C18—C17—H17	116.9
C5—C4—H4	119.8	C23—C18—C19	116.1 (3)
C3—C4—H4	119.8	C23—C18—C17	123.7 (3)
C4—C5—C6	121.0 (5)	C19—C18—C17	120.2 (3)
C4—C5—H5	119.5	C20—C19—C18	121.8 (3)
C6—C5—H5	119.5	C20—C19—H19	119.1
C5—C6—C1	120.1 (5)	C18—C19—H19	119.1
C5—C6—H6	120.0	C19—C20—C21	120.9 (4)
C1—C6—H6	120.0	C19—C20—H20	119.5
C8—C7—C12	121.0 (3)	C21—C20—H20	119.5
C8—C7—N1	132.0 (3)	O3—C21—C20	116.5 (3)
C12—C7—N1	107.0 (3)	O3—C21—C22	124.9 (3)
C9—C8—C7	118.4 (3)	C20—C21—C22	118.6 (3)
C9—C8—H8	120.8	C23—C22—C21	120.3 (3)
C7—C8—H8	120.8	C23—C22—H22	119.9
C10—C9—C8	121.6 (4)	C21—C22—H22	119.9
C10—C9—H9	119.2	C22—C23—C18	122.2 (3)
C8—C9—H9	119.2	C22—C23—H23	118.9
C9—C10—C11	120.7 (4)	C18—C23—H23	118.9
C9—C10—H10	119.7	O3—C24—H24A	109.5
C11—C10—H10	119.7	O3—C24—H24B	109.5
C10—C11—C12	119.7 (4)	H24A—C24—H24B	109.5
C10—C11—H11	120.2	O3—C24—H24C	109.5
C12—C11—H11	120.2	H24A—C24—H24C	109.5
C11—C12—C7	118.6 (3)	H24B—C24—H24C	109.5
C11—C12—C13	133.0 (3)	C7—N1—C14	107.5 (2)
C7—C12—C13	108.4 (3)	C7—N1—S1	121.2 (2)
C14—C13—C12	108.6 (3)	C14—N1—S1	123.5 (2)
C14—C13—C15	127.4 (3)	C21—O3—C24	118.4 (3)
C12—C13—C15	123.8 (3)	O1—S1—O2	119.45 (15)
C13—C14—N1	108.3 (3)	O1—S1—N1	106.24 (14)
C13—C14—C16	129.2 (3)	O2—S1—N1	106.86 (14)
N1—C14—C16	122.3 (3)	O1—S1—C1	109.21 (16)
C13—C15—H15A	109.5	O2—S1—C1	109.19 (17)
C13—C15—H15B	109.5	N1—S1—C1	104.87 (14)

C6—C1—C2—C3	−1.1 (6)	C23—C18—C19—C20	−1.8 (5)
S1—C1—C2—C3	−177.7 (3)	C17—C18—C19—C20	177.5 (3)
C1—C2—C3—C4	0.2 (7)	C18—C19—C20—C21	0.7 (6)
C2—C3—C4—C5	0.2 (9)	C19—C20—C21—O3	−178.4 (4)
C3—C4—C5—C6	0.3 (9)	C19—C20—C21—C22	0.8 (6)
C4—C5—C6—C1	−1.1 (7)	O3—C21—C22—C23	178.1 (3)
C2—C1—C6—C5	1.5 (6)	C20—C21—C22—C23	−1.1 (5)
S1—C1—C6—C5	178.2 (3)	C21—C22—C23—C18	−0.1 (5)
C12—C7—C8—C9	−0.9 (5)	C19—C18—C23—C22	1.5 (5)
N1—C7—C8—C9	179.2 (3)	C17—C18—C23—C22	−177.7 (3)
C7—C8—C9—C10	−1.0 (6)	C8—C7—N1—C14	175.9 (3)
C8—C9—C10—C11	1.6 (6)	C12—C7—N1—C14	−4.0 (3)
C9—C10—C11—C12	−0.2 (6)	C8—C7—N1—S1	25.9 (4)
C10—C11—C12—C7	−1.7 (5)	C12—C7—N1—S1	−154.0 (2)
C10—C11—C12—C13	178.2 (3)	C13—C14—N1—C7	4.5 (3)
C8—C7—C12—C11	2.2 (5)	C16—C14—N1—C7	179.0 (3)
N1—C7—C12—C11	−177.8 (3)	C13—C14—N1—S1	153.6 (2)
C8—C7—C12—C13	−177.7 (3)	C16—C14—N1—S1	−31.8 (4)
N1—C7—C12—C13	2.2 (3)	C20—C21—O3—C24	175.7 (4)
C11—C12—C13—C14	−179.4 (3)	C22—C21—O3—C24	−3.5 (6)
C7—C12—C13—C14	0.5 (4)	C7—N1—S1—O1	−48.0 (3)
C11—C12—C13—C15	5.1 (6)	C14—N1—S1—O1	166.9 (2)
C7—C12—C13—C15	−175.0 (3)	C7—N1—S1—O2	−176.6 (2)
C12—C13—C14—N1	−3.0 (3)	C14—N1—S1—O2	38.3 (3)
C15—C13—C14—N1	172.2 (3)	C7—N1—S1—C1	67.6 (3)
C12—C13—C14—C16	−177.1 (3)	C14—N1—S1—C1	−77.5 (3)
C15—C13—C14—C16	−1.8 (5)	C2—C1—S1—O1	−170.2 (3)
C13—C14—C16—C17	−45.6 (5)	C6—C1—S1—O1	13.1 (3)
N1—C14—C16—C17	141.1 (3)	C2—C1—S1—O2	−37.9 (3)
C14—C16—C17—C18	175.1 (3)	C6—C1—S1—O2	145.3 (3)
C16—C17—C18—C23	−3.2 (5)	C2—C1—S1—N1	76.3 (3)
C16—C17—C18—C19	177.6 (3)	C6—C1—S1—N1	−100.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C7–C12 and C18–C23 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.46	3.249 (5)	143
C15—H15C···Cg4ⁱⁱ	0.96	2.82	3.759 (4)	167
C24—H24A···Cg3ⁱⁱⁱ	0.96	2.84	3.634 (6)	140
C24—H24C···Cg2ⁱⁱⁱ	0.96	2.88	3.520 (5)	125

Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1/2, y+3/2, −z−1/2; (iii) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C7–C12 and C18–C23 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.46	3.249 (5)	143
C15—H15C···Cg4ⁱⁱ	0.96	2.82	3.759 (4)	167
C24—H24A···Cg3ⁱⁱⁱ	0.96	2.84	3.634 (6)	140
C24—H24C···Cg2ⁱⁱⁱ	0.96	2.88	3.520 (5)	125

Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1/2, y+3/2, −z−1/2; (iii) x, y, z+1.

Acknowledgements

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

References

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Volume 71| Part 10| October 2015| Pages o723-o724

doi:10.1107/S2056989015016631

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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