(3-Phenyl-sulfanyl-1-phenyl-sulfonyl-1H-indol-2-yl)methyl acetate.

In the title compound, C(23)H(19)NO(4)S(2), the indole ring system makes dihedral angles of 89.6 (1) and 84.5 (8)° with the phenyl-sulfonyl and phenyl-sulfanyl rings, respectively. In the crystal, the mol-ecules are linked into C(10) chains running along the c axis by an inter-molecular C-H⋯O hydrogen bond. In addition, the crystal packing is stabilized by C-H⋯π inter-actions.

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 = 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

Δρmax = 0.26 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C23H19NO4S2	F(000) = 912
Mr = 437.51	Dx = 1.387 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5235 reflections
a = 14.6530 (6) Å	θ = 1.4–28.4°
b = 9.4482 (4) Å	µ = 0.29 mm−1
c = 15.2461 (7) Å	T = 293 K
β = 97.055 (3)°	Block, white
V = 2094.76 (16) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5235 independent reflections
Radiation source: fine-focus sealed tube	3638 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 28.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.981, Tmax = 0.985	k = −11→12
19397 measured reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.4791P] where P = (Fo2 + 2Fc2)/3
5235 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.16888 (11)	0.62556 (16)	0.35882 (10)	0.0387 (4)
C2	0.09311 (12)	0.55131 (18)	0.38072 (11)	0.0463 (4)
H2	0.0349	0.5645	0.3500	0.056*
C3	0.10805 (13)	0.45722 (19)	0.44998 (12)	0.0530 (4)
H3	0.0586	0.4057	0.4660	0.064*
C4	0.19466 (14)	0.43671 (19)	0.49671 (12)	0.0543 (5)
H4	0.2019	0.3728	0.5434	0.065*
C5	0.26938 (13)	0.50947 (18)	0.47475 (11)	0.0482 (4)
H5	0.3273	0.4959	0.5061	0.058*
C6	0.25666 (11)	0.60461 (16)	0.40419 (10)	0.0410 (4)
C7	0.31844 (11)	0.69850 (17)	0.36612 (11)	0.0424 (4)
C8	0.27026 (11)	0.77336 (17)	0.30037 (11)	0.0422 (4)
C9	0.30417 (12)	0.89164 (18)	0.24908 (12)	0.0494 (4)
H9A	0.3708	0.8898	0.2536	0.059*
H9B	0.2795	0.8842	0.1872	0.059*
C10	0.28751 (13)	1.14037 (19)	0.24295 (13)	0.0534 (4)
C11	0.2490 (2)	1.2651 (2)	0.28528 (19)	0.0882 (8)
H11A	0.2619	1.3495	0.2540	0.132*
H11B	0.2765	1.2722	0.3456	0.132*
H11C	0.1837	1.2541	0.2836	0.132*
C12	0.07661 (13)	0.49985 (18)	0.14300 (12)	0.0522 (4)
H12	0.0490	0.4775	0.1930	0.063*
C13	0.08604 (15)	0.3989 (2)	0.08013 (13)	0.0622 (5)
H13	0.0656	0.3071	0.0880	0.075*
C14	0.12545 (14)	0.4326 (2)	0.00578 (13)	0.0600 (5)
H14	0.1311	0.3637	−0.0368	0.072*
C15	0.15663 (14)	0.5672 (2)	−0.00607 (12)	0.0598 (5)
H15	0.1831	0.5894	−0.0567	0.072*
C16	0.14880 (12)	0.66998 (19)	0.05698 (11)	0.0506 (4)
H16	0.1703	0.7612	0.0495	0.061*
C17	0.10864 (10)	0.63531 (16)	0.13106 (10)	0.0391 (3)
C18	0.43670 (12)	0.7939 (2)	0.50554 (13)	0.0557 (5)
C19	0.39555 (14)	0.9229 (3)	0.51322 (15)	0.0681 (6)
H19	0.3656	0.9675	0.4634	0.082*
C20	0.39877 (17)	0.9870 (3)	0.59577 (18)	0.0861 (8)
H20	0.3692	1.0730	0.6018	0.103*
C21	0.4459 (2)	0.9222 (4)	0.66824 (17)	0.0938 (9)
H21	0.4489	0.9654	0.7233	0.113*
C22	0.48819 (18)	0.7960 (4)	0.66036 (17)	0.0896 (8)
H22	0.5203	0.7537	0.7099	0.108*
C23	0.48383 (15)	0.7297 (3)	0.57906 (15)	0.0736 (6)
H23	0.5123	0.6426	0.5739	0.088*
N1	0.17660 (9)	0.73225 (14)	0.29437 (9)	0.0405 (3)
O1	0.01013 (8)	0.74327 (13)	0.24414 (9)	0.0550 (3)
O2	0.11545 (9)	0.90024 (12)	0.17575 (8)	0.0561 (3)
O3	0.27314 (8)	1.02147 (12)	0.28681 (8)	0.0544 (3)
O4	0.32709 (11)	1.14258 (15)	0.17888 (9)	0.0712 (4)
S1	0.09482 (3)	0.76585 (4)	0.21008 (3)	0.04212 (12)
S2	0.43695 (3)	0.71174 (6)	0.40011 (3)	0.05871 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0493 (9)	0.0344 (8)	0.0324 (8)	−0.0008 (7)	0.0050 (7)	−0.0040 (7)
C2	0.0514 (10)	0.0450 (9)	0.0421 (10)	−0.0070 (8)	0.0040 (8)	−0.0032 (8)
C3	0.0662 (12)	0.0463 (10)	0.0473 (11)	−0.0130 (9)	0.0105 (9)	0.0007 (8)
C4	0.0806 (13)	0.0408 (9)	0.0405 (10)	−0.0069 (9)	0.0033 (9)	0.0048 (8)
C5	0.0604 (11)	0.0417 (9)	0.0404 (9)	0.0018 (8)	−0.0027 (8)	−0.0027 (8)
C6	0.0519 (9)	0.0353 (8)	0.0355 (9)	0.0005 (7)	0.0036 (7)	−0.0066 (7)
C7	0.0454 (9)	0.0422 (9)	0.0397 (9)	−0.0008 (7)	0.0057 (7)	−0.0065 (7)
C8	0.0481 (9)	0.0408 (9)	0.0390 (9)	−0.0030 (7)	0.0105 (7)	−0.0067 (7)
C9	0.0580 (10)	0.0438 (9)	0.0487 (10)	−0.0043 (8)	0.0162 (8)	−0.0032 (8)
C10	0.0585 (11)	0.0451 (10)	0.0539 (12)	−0.0092 (8)	−0.0044 (9)	0.0015 (9)
C11	0.113 (2)	0.0501 (13)	0.102 (2)	0.0067 (12)	0.0184 (16)	−0.0035 (13)
C12	0.0707 (12)	0.0442 (10)	0.0436 (10)	−0.0074 (8)	0.0148 (9)	0.0013 (8)
C13	0.0913 (15)	0.0389 (10)	0.0581 (12)	−0.0086 (10)	0.0158 (11)	−0.0035 (9)
C14	0.0825 (14)	0.0500 (11)	0.0482 (11)	0.0101 (10)	0.0100 (10)	−0.0079 (9)
C15	0.0806 (13)	0.0579 (12)	0.0446 (11)	0.0002 (10)	0.0220 (10)	0.0007 (9)
C16	0.0657 (11)	0.0422 (9)	0.0455 (10)	−0.0056 (8)	0.0128 (9)	0.0043 (8)
C17	0.0436 (8)	0.0376 (8)	0.0354 (9)	0.0030 (7)	0.0015 (7)	0.0017 (7)
C18	0.0447 (10)	0.0705 (13)	0.0511 (11)	−0.0171 (9)	0.0025 (8)	−0.0018 (10)
C19	0.0653 (13)	0.0789 (15)	0.0596 (13)	−0.0093 (11)	0.0061 (10)	−0.0100 (11)
C20	0.0887 (17)	0.0921 (18)	0.0806 (18)	−0.0225 (14)	0.0230 (14)	−0.0285 (15)
C21	0.101 (2)	0.126 (3)	0.0559 (15)	−0.0570 (19)	0.0151 (14)	−0.0210 (17)
C22	0.0854 (18)	0.126 (2)	0.0537 (15)	−0.0416 (17)	−0.0083 (12)	0.0084 (16)
C23	0.0645 (13)	0.0873 (16)	0.0653 (15)	−0.0191 (11)	−0.0060 (11)	0.0076 (13)
N1	0.0465 (7)	0.0395 (7)	0.0350 (7)	−0.0020 (6)	0.0034 (6)	0.0009 (6)
O1	0.0473 (7)	0.0625 (8)	0.0560 (8)	0.0126 (6)	0.0097 (6)	−0.0015 (6)
O2	0.0733 (8)	0.0355 (6)	0.0579 (8)	0.0073 (6)	0.0010 (6)	0.0053 (6)
O3	0.0705 (8)	0.0421 (7)	0.0537 (7)	−0.0073 (6)	0.0205 (6)	−0.0047 (6)
O4	0.0962 (11)	0.0635 (9)	0.0545 (9)	−0.0183 (8)	0.0113 (8)	0.0085 (7)
S1	0.0477 (2)	0.0375 (2)	0.0408 (2)	0.00722 (17)	0.00382 (18)	0.00013 (17)
S2	0.0446 (3)	0.0741 (3)	0.0573 (3)	−0.0010 (2)	0.0058 (2)	−0.0084 (3)

C1—C2	1.388 (2)	C12—C17	1.383 (2)
C1—C6	1.398 (2)	C12—H12	0.9300
C1—N1	1.422 (2)	C13—C14	1.371 (3)
C2—C3	1.377 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.371 (3)
C3—C4	1.391 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.381 (3)
C4—C5	1.369 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.376 (2)
C5—C6	1.397 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—S1	1.7532 (16)
C6—C7	1.440 (2)	C18—C19	1.371 (3)
C7—C8	1.353 (2)	C18—C23	1.382 (3)
C7—S2	1.7545 (17)	C18—S2	1.785 (2)
C8—N1	1.418 (2)	C19—C20	1.392 (3)
C8—C9	1.484 (2)	C19—H19	0.9300
C9—O3	1.451 (2)	C20—C21	1.373 (4)
C9—H9A	0.9700	C20—H20	0.9300
C9—H9B	0.9700	C21—C22	1.356 (4)
C10—O4	1.196 (2)	C21—H21	0.9300
C10—O3	1.337 (2)	C22—C23	1.383 (4)
C10—C11	1.488 (3)	C22—H22	0.9300
C11—H11A	0.9600	C23—H23	0.9300
C11—H11B	0.9600	N1—S1	1.6763 (14)
C11—H11C	0.9600	O1—S1	1.4190 (12)
C12—C13	1.371 (3)	O2—S1	1.4201 (12)
C2—C1—C6	121.60 (15)	C12—C13—H13	119.8
C2—C1—N1	131.17 (15)	C14—C13—H13	119.8
C6—C1—N1	107.21 (13)	C15—C14—C13	120.33 (18)
C3—C2—C1	117.01 (17)	C15—C14—H14	119.8
C3—C2—H2	121.5	C13—C14—H14	119.8
C1—C2—H2	121.5	C14—C15—C16	120.22 (17)
C2—C3—C4	122.14 (17)	C14—C15—H15	119.9
C2—C3—H3	118.9	C16—C15—H15	119.9
C4—C3—H3	118.9	C17—C16—C15	118.97 (16)
C5—C4—C3	120.78 (17)	C17—C16—H16	120.5
C5—C4—H4	119.6	C15—C16—H16	120.5
C3—C4—H4	119.6	C16—C17—C12	120.98 (15)
C4—C5—C6	118.46 (17)	C16—C17—S1	119.59 (13)
C4—C5—H5	120.8	C12—C17—S1	119.40 (12)
C6—C5—H5	120.8	C19—C18—C23	120.1 (2)
C5—C6—C1	120.00 (15)	C19—C18—S2	120.85 (16)
C5—C6—C7	132.54 (16)	C23—C18—S2	118.90 (18)
C1—C6—C7	107.41 (14)	C18—C19—C20	119.8 (2)
C8—C7—C6	108.92 (14)	C18—C19—H19	120.1
C8—C7—S2	126.09 (13)	C20—C19—H19	120.1
C6—C7—S2	124.99 (13)	C21—C20—C19	119.4 (3)
C7—C8—N1	108.51 (14)	C21—C20—H20	120.3
C7—C8—C9	127.31 (15)	C19—C20—H20	120.3
N1—C8—C9	123.79 (15)	C22—C21—C20	120.7 (3)
O3—C9—C8	106.62 (12)	C22—C21—H21	119.6
O3—C9—H9A	110.4	C20—C21—H21	119.6
C8—C9—H9A	110.4	C21—C22—C23	120.4 (3)
O3—C9—H9B	110.4	C21—C22—H22	119.8
C8—C9—H9B	110.4	C23—C22—H22	119.8
H9A—C9—H9B	108.6	C18—C23—C22	119.4 (3)
O4—C10—O3	123.03 (18)	C18—C23—H23	120.3
O4—C10—C11	126.05 (19)	C22—C23—H23	120.3
O3—C10—C11	110.92 (18)	C8—N1—C1	107.94 (13)
C10—C11—H11A	109.5	C8—N1—S1	126.33 (11)
C10—C11—H11B	109.5	C1—N1—S1	123.64 (11)
H11A—C11—H11B	109.5	C10—O3—C9	115.82 (13)
C10—C11—H11C	109.5	O1—S1—O2	120.31 (7)
H11A—C11—H11C	109.5	O1—S1—N1	105.42 (7)
H11B—C11—H11C	109.5	O2—S1—N1	106.70 (7)
C13—C12—C17	119.13 (16)	O1—S1—C17	109.01 (8)
C13—C12—H12	120.4	O2—S1—C17	109.15 (8)
C17—C12—H12	120.4	N1—S1—C17	105.16 (7)
C12—C13—C14	120.36 (17)	C7—S2—C18	100.69 (8)
C6—C1—C2—C3	0.8 (2)	C19—C20—C21—C22	−0.9 (4)
N1—C1—C2—C3	−177.37 (16)	C20—C21—C22—C23	−0.5 (4)
C1—C2—C3—C4	0.2 (3)	C19—C18—C23—C22	0.7 (3)
C2—C3—C4—C5	−0.6 (3)	S2—C18—C23—C22	176.63 (16)
C3—C4—C5—C6	−0.1 (3)	C21—C22—C23—C18	0.6 (3)
C4—C5—C6—C1	1.1 (2)	C7—C8—N1—C1	−1.09 (17)
C4—C5—C6—C7	178.16 (17)	C9—C8—N1—C1	−174.33 (14)
C2—C1—C6—C5	−1.5 (2)	C7—C8—N1—S1	−165.03 (11)
N1—C1—C6—C5	177.06 (14)	C9—C8—N1—S1	21.7 (2)
C2—C1—C6—C7	−179.21 (14)	C2—C1—N1—C8	179.43 (16)
N1—C1—C6—C7	−0.66 (16)	C6—C1—N1—C8	1.06 (16)
C5—C6—C7—C8	−177.32 (17)	C2—C1—N1—S1	−16.1 (2)
C1—C6—C7—C8	−0.01 (18)	C6—C1—N1—S1	165.54 (11)
C5—C6—C7—S2	2.9 (3)	O4—C10—O3—C9	−3.4 (3)
C1—C6—C7—S2	−179.79 (12)	C11—C10—O3—C9	177.29 (17)
C6—C7—C8—N1	0.68 (18)	C8—C9—O3—C10	−172.38 (15)
S2—C7—C8—N1	−179.54 (11)	C8—N1—S1—O1	−163.03 (13)
C6—C7—C8—C9	173.61 (15)	C1—N1—S1—O1	35.40 (14)
S2—C7—C8—C9	−6.6 (2)	C8—N1—S1—O2	−34.03 (15)
C7—C8—C9—O3	−100.22 (19)	C1—N1—S1—O2	164.40 (12)
N1—C8—C9—O3	71.71 (19)	C8—N1—S1—C17	81.83 (14)
C17—C12—C13—C14	−1.0 (3)	C1—N1—S1—C17	−79.75 (13)
C12—C13—C14—C15	0.6 (3)	C16—C17—S1—O1	143.04 (14)
C13—C14—C15—C16	0.2 (3)	C12—C17—S1—O1	−35.16 (16)
C14—C15—C16—C17	−0.6 (3)	C16—C17—S1—O2	9.83 (16)
C15—C16—C17—C12	0.2 (3)	C12—C17—S1—O2	−168.37 (14)
C15—C16—C17—S1	−177.98 (14)	C16—C17—S1—N1	−104.33 (14)
C13—C12—C17—C16	0.6 (3)	C12—C17—S1—N1	77.48 (15)
C13—C12—C17—S1	178.76 (15)	C8—C7—S2—C18	110.04 (16)
C23—C18—C19—C20	−2.1 (3)	C6—C7—S2—C18	−70.22 (16)
S2—C18—C19—C20	−177.95 (16)	C19—C18—S2—C7	−58.87 (17)
C18—C19—C20—C21	2.2 (3)	C23—C18—S2—C7	125.22 (16)

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

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

Symmetry codes: (i) ; (ii) .