Ethyl 2-[(phenyl-sulfan-yl)meth-yl]-1-(phenyl-sulfon-yl)-1H-indole-3-carboxyl-ate.

In the title compound, C(24)H(21)NO(4)S(2), 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 mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions.

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 = 451.56

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.122

S = 0.82

4116 reflections

281 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

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.

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

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

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

C24H21NO4S2	F000 = 944
Mr = 451.56	Dx = 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 = 2.8–26.0º
b = 7.7140 (2) Å	µ = 0.28 mm−1
c = 26.770 (1) Å	T = 295 (2) K
β = 116.020 (2)º	Block, colourless
V = 2179.6 (2) Å3	0.24 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEX2 diffractometer	4116 independent reflections
Radiation source: fine-focus sealed tube	2128 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 295(2) K	θmax = 28.7º
ω– and φ–scan	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.927, Tmax = 0.947	k = −10→8
9731 measured reflections	l = −36→35

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82	(Δ/σ)max < 0.001
4116 reflections	Δρmax = 0.23 e Å−3
281 parameters	Δρmin = −0.18 e Å−3
9 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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