Ethyl 2-[(phenyl­sulfan­yl)meth­yl]-1-(phenyl­sulfon­yl)-1H-indole-3-carboxyl­ate

Chakkaravarthi, G.; Dhayalan, V.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536807068778

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o392

doi:10.1107/S1600536807068778

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Ethyl 2-[(phenylsulfanyl)methyl]-1-(phenylsulfonyl)-1H-indole-3-carboxylate

G. Chakkaravarthi,^a ^* V. Dhayalan,^b A. K. Mohanakrishnan ^b and V. Manivannan ^c

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 22 December 2007; accepted 29 December 2007; online 9 January 2008)

In the title compound, C₂₄H₂₁NO₄S₂, the phenyl rings form dihedral angles of 85.77 (9) and 85.22 (9)° and the ester group forms an angle of 12.61 (10)° with the indane ring. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions.

Related literature

For related literature, see: Allen et al. (1987 ); Nieto et al. (2005 ); Satis Kumar et al. (2006 ). A similar compound has been reported by Chakkaravarthi et al. (2007 ).

Experimental

Crystal data

C₂₄H₂₁NO₄S₂
M_r = 451.56
Monoclinic, P 2₁ /c
a = 11.745 (1) Å
b = 7.7140 (2) Å
c = 26.770 (1) Å
β = 116.020 (2)°
V = 2179.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 295 (2) K
0.24 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.927, T_max = 0.947
9731 measured reflections
4116 independent reflections
2128 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.122
S = 0.82
4116 reflections
281 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1	0.97	2.38	2.813 (4)	107
C7—H7B⋯O3	0.97	2.26	2.977 (4)	130
C11—H11⋯O4	0.93	2.42	2.932 (3)	115
C14—H14⋯O2	0.93	2.41	2.966 (3)	119
C24—H24⋯O2	0.93	2.52	2.898 (3)	105

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068778/rk2072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068778/rk2072Isup2.hkl

checkCIF report

Comment top

The benzenesulfonamide derivatives exhibit significant biological activities, such as antibacterial (Nieto et al., 2005). In the molecule of title compound (I) (Fig. 1), the bond lengths and angles are agree with the reported similar structures (Allen et al. 1987; Chakkaravarthi et al., 2007; Satis Kumar et al., 2006).

The phenyl rings C1–C6 and C19–C24 form the dihedral angles with the indane ring system of 85.77 (9)° and 85.22 (9)°, respectively. The dihedral angle between these phenyl rings is 4.26 (9)°. The ester group C16/O3/O4/C17/C18 forms a dihedral angle with the indane ring system of 12.61 (10)°.

The molecular structure of (I) (Fig. 1) is stabilized by intramolecular C—H···O interactions. A similar compound has been reported by Chakkaravarthi et al. (2007).

Related literature top

For related literature, see: Allen et al. (1987); Nieto et al. (2005); Satis Kumar et al. (2006). A similar compound has been reported by Chakkaravarthi et al. (2007).

Experimental top

To a well stirred suspension of sodium hydride (0.17 g, 3.55 mmol) in dry tetrahydrofurane (THF) (10 ml) at 273 K, a solution of thiophenol (0.36 ml, 3.55 mmol) in dry THF (10 ml) was slowly added over a period of 10 min. After the evaluation of hydrogen gas ceased a solution of ethyl 2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1 g, 2.36 mmol) in dry THF (10 ml) was added in dropwise with vigorous stirring. Then the reaction mixture was stirred for 2 h and then poured over crushed ice. The precipitated solid was filtered, washed with water and dried over calcium chloride. The crude sulfide was recrystallized from methanol. Single crystals suitable for X-ray analysis were grown by slow evaporation of a methanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of (I), with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Intramolecular H-bonds are shown as dotted lines.

Ethyl 2-[(phenylsulfanyl)methyl]-1-(phenylsulfonyl)-1H-indole- 3-carboxylate top

Crystal data top

C₂₄H₂₁NO₄S₂	F(000) = 944
M_r = 451.56	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10291 reflections
a = 11.745 (1) Å	θ = 2.8–26.0°
b = 7.7140 (2) Å	µ = 0.28 mm⁻¹
c = 26.770 (1) Å	T = 295 K
β = 116.020 (2)°	Block, colourless
V = 2179.6 (2) Å³	0.24 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEX2 diffractometer	4116 independent reflections
Radiation source: fine-focus sealed tube	2128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω– and ϕ–scan	θ_max = 28.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.927, T_max = 0.947	k = −10→8
9731 measured reflections	l = −36→35

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 0.82	w = 1/[σ²(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
4116 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.23 e Å⁻³
9 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₄H₂₁NO₄S₂	V = 2179.6 (2) Å³
M_r = 451.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.745 (1) Å	µ = 0.28 mm⁻¹
b = 7.7140 (2) Å	T = 295 K
c = 26.770 (1) Å	0.24 × 0.20 × 0.20 mm
β = 116.020 (2)°

Data collection top

Bruker Kappa APEX2 diffractometer	4116 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2128 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.947	R_int = 0.037
9731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	9 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 0.82	Δρ_max = 0.23 e Å⁻³
4116 reflections	Δρ_min = −0.18 e Å⁻³
281 parameters

Special details top

Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.75890 (7)	0.46511 (8)	0.02189 (3)	0.03776 (17)
S2	1.06434 (7)	0.72740 (9)	0.09115 (4)	0.0563 (2)
O1	0.84440 (19)	0.5349 (2)	0.00269 (8)	0.0471 (5)
O2	0.64341 (19)	0.5547 (2)	0.01066 (8)	0.0494 (5)
O3	1.2184 (2)	0.3917 (3)	0.22110 (10)	0.0725 (6)
O4	1.11279 (18)	0.3805 (3)	0.27290 (8)	0.0545 (5)
N1	0.8387 (2)	0.4502 (2)	0.09151 (9)	0.0362 (5)
C1	1.2195 (3)	0.7980 (3)	0.13616 (12)	0.0438 (6)
C2	1.2297 (3)	0.9673 (4)	0.15435 (13)	0.0546 (7)
H2	1.1570	1.0329	0.1457	0.066*
C3	1.3477 (3)	1.0396 (4)	0.18538 (15)	0.0661 (9)
H3	1.3537	1.1543	0.1970	0.079*
C4	1.4568 (3)	0.9438 (4)	0.19933 (15)	0.0700 (10)
H4	1.5360	0.9927	0.2203	0.084*
C5	1.4459 (3)	0.7738 (4)	0.18144 (14)	0.0628 (9)
H5	1.5184	0.7070	0.1911	0.075*
C6	1.3281 (2)	0.7019 (4)	0.14923 (13)	0.0552 (7)
H6	1.3221	0.5886	0.1364	0.066*
C7	1.0649 (2)	0.4937 (3)	0.10300 (12)	0.0423 (6)
H7A	1.0453	0.4325	0.0685	0.051*
H7B	1.1486	0.4581	0.1300	0.051*
C8	0.9695 (2)	0.4468 (3)	0.12382 (11)	0.0362 (6)
C9	0.9929 (2)	0.4064 (3)	0.17792 (10)	0.0367 (6)
C10	0.8719 (2)	0.3803 (3)	0.17934 (11)	0.0368 (6)
C11	0.8367 (3)	0.3384 (4)	0.22147 (12)	0.0470 (6)
H11	0.8978	0.3236	0.2579	0.056*
C12	0.7090 (3)	0.3194 (4)	0.20795 (13)	0.0539 (7)
H12	0.6848	0.2903	0.2356	0.065*
C13	0.6167 (3)	0.3430 (4)	0.15376 (13)	0.0513 (7)
H13	0.5318	0.3299	0.1459	0.062*
C14	0.6486 (3)	0.3858 (3)	0.11120 (12)	0.0431 (6)
H14	0.5871	0.4008	0.0749	0.052*
C15	0.7775 (2)	0.4055 (3)	0.12549 (10)	0.0358 (5)
C16	1.1197 (3)	0.3927 (3)	0.22444 (12)	0.0442 (6)
C17	1.2305 (3)	0.3585 (4)	0.32177 (12)	0.0626 (8)
H17A	1.2932	0.4401	0.3216	0.075*
H17B	1.2627	0.2419	0.3233	0.075*
C18	1.2026 (4)	0.3919 (5)	0.37179 (13)	0.0733 (10)
H18A	1.1788	0.5110	0.3717	0.110*
H18B	1.2770	0.3676	0.4055	0.110*
H18C	1.1346	0.3182	0.3694	0.110*
C19	0.7233 (2)	0.2500 (3)	−0.00112 (10)	0.0379 (5)
C20	0.8218 (3)	0.1388 (3)	0.00635 (12)	0.0507 (7)
H20	0.9054	0.1755	0.0254	0.061*
C21	0.7946 (3)	−0.0279 (3)	−0.01486 (13)	0.0594 (9)
H21	0.8597	−0.1040	−0.0105	0.071*
C22	0.6695 (3)	−0.0800 (4)	−0.04255 (13)	0.0607 (9)
H22	0.6507	−0.1915	−0.0571	0.073*
C23	0.5720 (3)	0.0317 (3)	−0.04881 (15)	0.0663 (9)
H23	0.4885	−0.0057	−0.0674	0.080*
C24	0.5977 (2)	0.1988 (3)	−0.02768 (14)	0.0576 (8)
H24	0.5326	0.2739	−0.0312	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0378 (4)	0.0385 (3)	0.0341 (4)	−0.0018 (3)	0.0132 (3)	0.0011 (3)
S2	0.0334 (4)	0.0581 (4)	0.0664 (6)	−0.0052 (3)	0.0118 (4)	0.0160 (4)
O1	0.0506 (12)	0.0494 (10)	0.0405 (11)	−0.0102 (9)	0.0194 (11)	0.0004 (8)
O2	0.0432 (12)	0.0476 (10)	0.0507 (13)	0.0090 (8)	0.0146 (11)	0.0063 (9)
O3	0.0350 (12)	0.1220 (18)	0.0579 (15)	0.0079 (12)	0.0179 (12)	0.0098 (13)
O4	0.0348 (11)	0.0834 (14)	0.0379 (11)	−0.0033 (10)	0.0092 (10)	0.0114 (10)
N1	0.0306 (11)	0.0451 (10)	0.0327 (12)	−0.0052 (9)	0.0136 (11)	−0.0034 (9)
C1	0.0366 (15)	0.0576 (16)	0.0390 (15)	−0.0023 (12)	0.0183 (14)	0.0082 (12)
C2	0.0505 (19)	0.0595 (17)	0.0534 (19)	0.0039 (14)	0.0223 (18)	0.0035 (14)
C3	0.072 (3)	0.0648 (19)	0.065 (2)	−0.0187 (18)	0.032 (2)	−0.0098 (17)
C4	0.051 (2)	0.097 (3)	0.056 (2)	−0.0244 (18)	0.019 (2)	−0.0037 (19)
C5	0.0363 (16)	0.084 (2)	0.067 (2)	−0.0003 (15)	0.0225 (18)	0.0078 (17)
C6	0.0403 (17)	0.0656 (18)	0.064 (2)	−0.0032 (14)	0.0267 (17)	−0.0010 (15)
C7	0.0326 (15)	0.0515 (13)	0.0454 (16)	−0.0013 (11)	0.0195 (15)	0.0035 (12)
C8	0.0307 (14)	0.0386 (12)	0.0393 (15)	−0.0014 (10)	0.0154 (13)	−0.0002 (10)
C9	0.0312 (14)	0.0415 (12)	0.0368 (15)	−0.0044 (10)	0.0142 (13)	−0.0031 (10)
C10	0.0331 (14)	0.0396 (12)	0.0380 (15)	−0.0005 (10)	0.0160 (13)	−0.0026 (11)
C11	0.0418 (16)	0.0620 (16)	0.0353 (15)	−0.0069 (13)	0.0151 (14)	−0.0027 (12)
C12	0.0500 (18)	0.0751 (18)	0.0461 (18)	−0.0146 (15)	0.0298 (17)	−0.0089 (14)
C13	0.0359 (16)	0.0649 (17)	0.059 (2)	−0.0088 (13)	0.0263 (16)	−0.0090 (15)
C14	0.0309 (14)	0.0548 (14)	0.0408 (16)	−0.0034 (11)	0.0132 (14)	−0.0052 (12)
C15	0.0363 (14)	0.0374 (12)	0.0349 (14)	−0.0072 (10)	0.0166 (13)	−0.0060 (10)
C16	0.0366 (15)	0.0502 (14)	0.0431 (16)	−0.0009 (11)	0.0150 (15)	0.0036 (12)
C17	0.0382 (17)	0.086 (2)	0.0483 (19)	−0.0086 (15)	0.0052 (17)	0.0149 (17)
C18	0.060 (2)	0.103 (3)	0.045 (2)	−0.0090 (19)	0.0121 (19)	0.0156 (17)
C19	0.0389 (15)	0.0421 (12)	0.0274 (13)	0.0013 (11)	0.0095 (13)	0.0045 (10)
C20	0.0489 (18)	0.0488 (15)	0.0510 (18)	−0.0011 (12)	0.0186 (17)	−0.0036 (13)
C21	0.068 (2)	0.0468 (15)	0.057 (2)	0.0111 (15)	0.021 (2)	0.0027 (14)
C22	0.079 (3)	0.0418 (15)	0.0470 (19)	−0.0043 (15)	0.014 (2)	0.0021 (13)
C23	0.051 (2)	0.0597 (18)	0.067 (2)	−0.0175 (15)	0.007 (2)	−0.0056 (16)
C24	0.0490 (19)	0.0538 (16)	0.062 (2)	−0.0009 (13)	0.0170 (18)	−0.0037 (15)

Geometric parameters (Å, º) top

S1—O1	1.4195 (18)	C10—C15	1.393 (4)
S1—O2	1.4318 (19)	C10—C11	1.398 (4)
S1—N1	1.683 (2)	C11—C12	1.388 (4)
S1—C19	1.755 (2)	C11—H11	0.9300
S2—C1	1.773 (3)	C12—C13	1.390 (4)
S2—C7	1.830 (3)	C12—H12	0.9300
O3—C16	1.201 (3)	C13—C14	1.386 (4)
O4—C16	1.338 (3)	C13—H13	0.9300
O4—C17	1.437 (3)	C14—C15	1.398 (4)
N1—C8	1.394 (3)	C14—H14	0.9300
N1—C15	1.427 (3)	C17—C18	1.533 (3)
C1—C6	1.381 (4)	C17—H17A	0.9700
C1—C2	1.381 (4)	C17—H17B	0.9700
C2—C3	1.383 (4)	C18—H18A	0.9600
C2—H2	0.9300	C18—H18B	0.9600
C3—C4	1.381 (3)	C18—H18C	0.9600
C3—H3	0.9300	C19—C20	1.383 (2)
C4—C5	1.383 (3)	C19—C24	1.385 (2)
C4—H4	0.9300	C20—C21	1.385 (2)
C5—C6	1.385 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.383 (4)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.498 (3)	C22—C23	1.382 (3)
C7—H7A	0.9700	C22—H22	0.9300
C7—H7B	0.9700	C23—C24	1.387 (3)
C8—C9	1.386 (3)	C23—H23	0.9300
C9—C10	1.453 (3)	C24—H24	0.9300
C9—C16	1.467 (4)

O1—S1—O2	119.78 (11)	C10—C11—H11	120.6
O1—S1—N1	106.73 (11)	C11—C12—C13	121.1 (3)
O2—S1—N1	106.35 (11)	C11—C12—H12	119.4
O1—S1—C19	109.19 (11)	C13—C12—H12	119.4
O2—S1—C19	108.93 (11)	C14—C13—C12	121.4 (3)
N1—S1—C19	104.79 (10)	C14—C13—H13	119.3
C1—S2—C7	105.10 (12)	C12—C13—H13	119.3
C16—O4—C17	116.6 (2)	C13—C14—C15	116.8 (3)
C8—N1—C15	109.02 (19)	C13—C14—H14	121.6
C8—N1—S1	127.98 (17)	C15—C14—H14	121.6
C15—N1—S1	122.05 (17)	C10—C15—C14	122.9 (2)
C6—C1—C2	119.4 (3)	C10—C15—N1	107.4 (2)
C6—C1—S2	124.5 (2)	C14—C15—N1	129.8 (2)
C2—C1—S2	115.7 (2)	O3—C16—O4	122.9 (3)
C1—C2—C3	120.1 (3)	O3—C16—C9	126.2 (3)
C1—C2—H2	119.9	O4—C16—C9	110.9 (2)
C3—C2—H2	119.9	O4—C17—C18	106.6 (2)
C4—C3—C2	120.9 (3)	O4—C17—H17A	110.4
C4—C3—H3	119.6	C18—C17—H17A	110.4
C2—C3—H3	119.6	O4—C17—H17B	110.4
C3—C4—C5	118.7 (3)	C18—C17—H17B	110.4
C3—C4—H4	120.7	H17A—C17—H17B	108.6
C5—C4—H4	120.7	C17—C18—H18A	109.5
C4—C5—C6	120.8 (3)	C17—C18—H18B	109.5
C4—C5—H5	119.6	H18A—C18—H18B	109.5
C6—C5—H5	119.6	C17—C18—H18C	109.5
C1—C6—C5	120.1 (3)	H18A—C18—H18C	109.5
C1—C6—H6	120.0	H18B—C18—H18C	109.5
C5—C6—H6	120.0	C20—C19—C24	122.2 (2)
C8—C7—S2	110.86 (17)	C20—C19—S1	118.70 (18)
C8—C7—H7A	109.5	C24—C19—S1	119.09 (17)
S2—C7—H7A	109.5	C19—C20—C21	119.2 (3)
C8—C7—H7B	109.5	C19—C20—H20	120.4
S2—C7—H7B	109.5	C21—C20—H20	120.4
H7A—C7—H7B	108.1	C22—C21—C20	119.3 (3)
C9—C8—N1	108.2 (2)	C22—C21—H21	120.3
C9—C8—C7	127.3 (2)	C20—C21—H21	120.3
N1—C8—C7	124.4 (2)	C23—C22—C21	120.8 (3)
C8—C9—C10	108.1 (2)	C23—C22—H22	119.6
C8—C9—C16	124.4 (2)	C21—C22—H22	119.6
C10—C9—C16	127.5 (2)	C22—C23—C24	120.6 (3)
C15—C10—C11	119.0 (2)	C22—C23—H23	119.7
C15—C10—C9	107.3 (2)	C24—C23—H23	119.7
C11—C10—C9	133.8 (3)	C19—C24—C23	117.8 (2)
C12—C11—C10	118.8 (3)	C19—C24—H24	121.1
C12—C11—H11	120.6	C23—C24—H24	121.1

O1—S1—N1—C8	−20.4 (2)	C11—C12—C13—C14	0.2 (4)
O2—S1—N1—C8	−149.37 (19)	C12—C13—C14—C15	−0.5 (4)
C19—S1—N1—C8	95.3 (2)	C11—C10—C15—C14	−1.9 (3)
O1—S1—N1—C15	171.99 (17)	C9—C10—C15—C14	178.2 (2)
O2—S1—N1—C15	43.0 (2)	C11—C10—C15—N1	178.6 (2)
C19—S1—N1—C15	−72.3 (2)	C9—C10—C15—N1	−1.3 (2)
C7—S2—C1—C6	34.8 (3)	C13—C14—C15—C10	1.4 (4)
C7—S2—C1—C2	−151.5 (2)	C13—C14—C15—N1	−179.3 (2)
C6—C1—C2—C3	0.0 (4)	C8—N1—C15—C10	2.0 (2)
S2—C1—C2—C3	−174.0 (2)	S1—N1—C15—C10	171.65 (15)
C1—C2—C3—C4	−0.9 (5)	C8—N1—C15—C14	−177.5 (2)
C2—C3—C4—C5	0.3 (5)	S1—N1—C15—C14	−7.8 (3)
C3—C4—C5—C6	1.3 (5)	C17—O4—C16—O3	−2.5 (4)
C2—C1—C6—C5	1.5 (4)	C17—O4—C16—C9	177.3 (2)
S2—C1—C6—C5	175.0 (2)	C8—C9—C16—O3	−10.4 (4)
C4—C5—C6—C1	−2.2 (5)	C10—C9—C16—O3	169.3 (3)
C1—S2—C7—C8	119.3 (2)	C8—C9—C16—O4	169.8 (2)
C15—N1—C8—C9	−1.9 (2)	C10—C9—C16—O4	−10.5 (3)
S1—N1—C8—C9	−170.77 (17)	C16—O4—C17—C18	166.6 (3)
C15—N1—C8—C7	−177.4 (2)	O1—S1—C19—C20	48.4 (2)
S1—N1—C8—C7	13.7 (3)	O2—S1—C19—C20	−179.2 (2)
S2—C7—C8—C9	−103.3 (3)	N1—S1—C19—C20	−65.7 (2)
S2—C7—C8—N1	71.4 (3)	O1—S1—C19—C24	−129.6 (2)
N1—C8—C9—C10	1.1 (3)	O2—S1—C19—C24	2.9 (3)
C7—C8—C9—C10	176.5 (2)	N1—S1—C19—C24	116.4 (2)
N1—C8—C9—C16	−179.2 (2)	C24—C19—C20—C21	2.1 (4)
C7—C8—C9—C16	−3.8 (4)	S1—C19—C20—C21	−175.8 (2)
C8—C9—C10—C15	0.2 (3)	C19—C20—C21—C22	−0.6 (4)
C16—C9—C10—C15	−179.6 (2)	C20—C21—C22—C23	−0.6 (5)
C8—C9—C10—C11	−179.7 (3)	C21—C22—C23—C24	0.3 (5)
C16—C9—C10—C11	0.6 (4)	C20—C19—C24—C23	−2.3 (5)
C15—C10—C11—C12	1.5 (4)	S1—C19—C24—C23	175.6 (2)
C9—C10—C11—C12	−178.6 (3)	C22—C23—C24—C19	1.0 (5)
C10—C11—C12—C13	−0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.97	2.38	2.813 (4)	107
C7—H7B···O3	0.97	2.26	2.977 (4)	130
C11—H11···O4	0.93	2.42	2.932 (3)	115
C14—H14···O2	0.93	2.41	2.966 (3)	119
C24—H24···O2	0.93	2.52	2.898 (3)	105

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁NO₄S₂
M_r	451.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.745 (1), 7.7140 (2), 26.770 (1)
β (°)	116.020 (2)
V (Å³)	2179.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.24 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.927, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	9731, 4116, 2128
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.122, 0.82
No. of reflections	4116
No. of parameters	281
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.97	2.38	2.813 (4)	107
C7—H7B···O3	0.97	2.26	2.977 (4)	130
C11—H11···O4	0.93	2.42	2.932 (3)	115
C14—H14···O2	0.93	2.41	2.966 (3)	119
C24—H24···O2	0.93	2.52	2.898 (3)	105

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2004). APEX2. Version 1.0-27. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361–369. Web of Science CrossRef PubMed CAS Google Scholar
Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o5388–o5389. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

Ethyl 2-[(phenyl­sulfan­yl)meth­yl]-1-(phenyl­sulfon­yl)-1H-indole-3-carboxyl­ate

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organic compounds

Ethyl 2-[(phenylsulfanyl)methyl]-1-(phenylsulfonyl)-1H-indole-3-carboxylate