N-[(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl]acetamide.

In the title compound, C(23)H(20)N(2)O(3)S(2), the phenylsulfonyl ring and phenylthio ring make dihedral angles of 66.5 (7) and 81.2 (6)°, respectively, with the indole unit. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of N-H⋯O hydrogen bonds with graph-set motif R(2) (2)(14). The crystal structure is further stabilized by weak inter-molecular C-H⋯O and very weak C-H⋯π inter-actions.

Related literature

For the biological activity 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 a related structure, see: Ravishankar et al. (2005 ▶).

Experimental

Crystal data

C23H20N2O3S2

M = 436.53

Triclinic,

a = 8.8129 (2) Å

b = 10.8880 (3) Å

c = 11.3711 (3) Å

α = 86.698 (1)°

β = 76.494 (1)°

γ = 83.317 (1)°

V = 1053.21 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.943, T max = 0.953

28160 measured reflections

7167 independent reflections

5294 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 0.98

7167 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.39 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: 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/S1600536809012525/bt2922sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012525/bt2922Isup2.hkl

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

C23H20N2O3S2	Z = 2
Mr = 436.53	F(000) = 456
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8129 (2) Å	Cell parameters from 7167 reflections
b = 10.8880 (3) Å	θ = 2.4–31.9°
c = 11.3711 (3) Å	µ = 0.28 mm−1
α = 86.698 (1)°	T = 293 K
β = 76.494 (1)°	Block, colourless
γ = 83.317 (1)°	0.21 × 0.19 × 0.17 mm
V = 1053.21 (5) Å3

Bruker Kappa APEXII CCD diffractometer	7167 independent reflections
Radiation source: fine-focus sealed tube	5294 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 31.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.943, Tmax = 0.953	k = −16→16
28160 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.2774P] where P = (Fo2 + 2Fc2)/3
7167 reflections	(Δ/σ)max = 0.005
272 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.39 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	0.80217 (15)	0.18662 (12)	0.83970 (11)	0.0347 (3)
C2	0.79544 (18)	0.07935 (15)	0.91125 (14)	0.0470 (3)
H2	0.8532	0.0644	0.9703	0.056*
C3	0.6993 (2)	−0.00414 (16)	0.89092 (17)	0.0567 (4)
H3	0.6929	−0.0775	0.9370	0.068*
C4	0.6116 (2)	0.01768 (16)	0.80390 (17)	0.0561 (4)
H4	0.5467	−0.0404	0.7937	0.067*
C5	0.61930 (18)	0.12411 (15)	0.73246 (14)	0.0465 (3)
H5	0.5611	0.1385	0.6736	0.056*
C6	0.71616 (15)	0.20927 (12)	0.75069 (11)	0.0348 (3)
C7	0.74318 (15)	0.33121 (12)	0.69884 (11)	0.0338 (3)
C8	0.83792 (15)	0.38163 (12)	0.75660 (11)	0.0329 (2)
C9	0.87341 (16)	0.51288 (13)	0.75136 (13)	0.0393 (3)
H9A	0.9854	0.5152	0.7415	0.047*
H9B	0.8427	0.5560	0.6822	0.047*
C10	0.64041 (17)	0.62259 (15)	0.87510 (15)	0.0463 (3)
C11	0.5609 (2)	0.66919 (19)	0.99829 (18)	0.0619 (5)
H11A	0.4948	0.7443	0.9901	0.093*
H11B	0.6387	0.6850	1.0405	0.093*
H11C	0.4982	0.6081	1.0430	0.093*
C12	1.17375 (14)	0.22315 (13)	0.72453 (12)	0.0355 (3)
C13	1.23409 (17)	0.30613 (15)	0.63391 (14)	0.0458 (3)
H13	1.2222	0.3904	0.6477	0.055*
C14	1.31247 (19)	0.26126 (19)	0.52229 (16)	0.0560 (4)
H14	1.3537	0.3157	0.4601	0.067*
C15	1.3295 (2)	0.1370 (2)	0.50313 (16)	0.0602 (5)
H15	1.3821	0.1075	0.4277	0.072*
C16	1.2700 (2)	0.05551 (18)	0.59387 (19)	0.0656 (5)
H16	1.2830	−0.0288	0.5798	0.079*
C17	1.19143 (19)	0.09758 (15)	0.70519 (16)	0.0517 (4)
H17	1.1506	0.0425	0.7669	0.062*
C18	0.76928 (15)	0.32193 (12)	0.45609 (11)	0.0336 (3)
C19	0.90885 (16)	0.24822 (14)	0.45385 (12)	0.0417 (3)
H19	0.9484	0.2367	0.5232	0.050*
C20	0.98919 (19)	0.19193 (16)	0.34812 (14)	0.0503 (4)
H20	1.0825	0.1418	0.3468	0.060*
C21	0.9327 (2)	0.20926 (16)	0.24488 (14)	0.0512 (4)
H21	0.9882	0.1719	0.1738	0.061*
C22	0.7938 (2)	0.28199 (17)	0.24709 (13)	0.0524 (4)
H22	0.7551	0.2934	0.1774	0.063*
C23	0.71127 (17)	0.33808 (15)	0.35210 (13)	0.0440 (3)
H23	0.6169	0.3867	0.3533	0.053*
N1	0.87779 (12)	0.29375 (10)	0.84621 (9)	0.0346 (2)
N2	0.78974 (13)	0.57402 (11)	0.86117 (11)	0.0403 (3)
H2A	0.8371	0.5792	0.9185	0.048*
O1	1.06998 (14)	0.18125 (12)	0.95384 (10)	0.0559 (3)
O2	1.09978 (14)	0.39630 (11)	0.88318 (11)	0.0552 (3)
O3	0.57273 (17)	0.62503 (18)	0.79379 (14)	0.0910 (5)
S1	1.06294 (4)	0.27656 (3)	0.86411 (3)	0.03906 (10)
S2	0.65950 (4)	0.40353 (3)	0.58434 (3)	0.04266 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0339 (6)	0.0363 (7)	0.0294 (6)	0.0033 (5)	−0.0017 (5)	−0.0011 (5)
C2	0.0472 (8)	0.0473 (8)	0.0409 (8)	0.0023 (6)	−0.0049 (6)	0.0087 (6)
C3	0.0589 (10)	0.0442 (9)	0.0590 (10)	−0.0056 (7)	−0.0003 (8)	0.0117 (7)
C4	0.0557 (9)	0.0456 (9)	0.0646 (11)	−0.0137 (7)	−0.0041 (8)	−0.0036 (8)
C5	0.0465 (8)	0.0474 (8)	0.0459 (8)	−0.0054 (6)	−0.0093 (6)	−0.0084 (6)
C6	0.0363 (6)	0.0365 (7)	0.0288 (6)	0.0022 (5)	−0.0039 (5)	−0.0048 (5)
C7	0.0373 (6)	0.0350 (6)	0.0270 (5)	0.0056 (5)	−0.0072 (5)	−0.0034 (5)
C8	0.0341 (6)	0.0346 (6)	0.0268 (5)	0.0043 (5)	−0.0043 (4)	−0.0025 (5)
C9	0.0388 (6)	0.0359 (7)	0.0403 (7)	−0.0002 (5)	−0.0049 (5)	−0.0030 (5)
C10	0.0393 (7)	0.0476 (8)	0.0508 (8)	0.0029 (6)	−0.0097 (6)	−0.0097 (7)
C11	0.0522 (9)	0.0638 (11)	0.0635 (11)	0.0005 (8)	0.0013 (8)	−0.0246 (9)
C12	0.0307 (6)	0.0404 (7)	0.0362 (6)	−0.0001 (5)	−0.0105 (5)	−0.0041 (5)
C13	0.0396 (7)	0.0441 (8)	0.0503 (8)	−0.0011 (6)	−0.0060 (6)	0.0022 (6)
C14	0.0432 (8)	0.0730 (12)	0.0446 (8)	−0.0027 (7)	0.0002 (6)	0.0076 (8)
C15	0.0448 (8)	0.0834 (14)	0.0490 (9)	−0.0026 (8)	−0.0006 (7)	−0.0234 (9)
C16	0.0572 (10)	0.0559 (11)	0.0783 (13)	−0.0077 (8)	0.0028 (9)	−0.0295 (10)
C17	0.0490 (8)	0.0422 (8)	0.0576 (9)	−0.0052 (6)	0.0015 (7)	−0.0055 (7)
C18	0.0365 (6)	0.0355 (6)	0.0295 (6)	−0.0043 (5)	−0.0093 (5)	0.0010 (5)
C19	0.0411 (7)	0.0508 (8)	0.0330 (6)	0.0029 (6)	−0.0113 (5)	−0.0029 (6)
C20	0.0460 (8)	0.0584 (10)	0.0411 (8)	0.0068 (7)	−0.0043 (6)	−0.0064 (7)
C21	0.0606 (9)	0.0569 (10)	0.0322 (7)	−0.0065 (7)	−0.0015 (6)	−0.0070 (6)
C22	0.0645 (10)	0.0649 (10)	0.0310 (7)	−0.0076 (8)	−0.0170 (7)	−0.0010 (7)
C23	0.0449 (7)	0.0534 (9)	0.0355 (7)	−0.0003 (6)	−0.0163 (6)	0.0022 (6)
N1	0.0343 (5)	0.0400 (6)	0.0282 (5)	0.0025 (4)	−0.0076 (4)	−0.0017 (4)
N2	0.0391 (6)	0.0397 (6)	0.0439 (6)	0.0019 (5)	−0.0137 (5)	−0.0120 (5)
O1	0.0594 (7)	0.0743 (8)	0.0344 (5)	0.0054 (6)	−0.0204 (5)	0.0089 (5)
O2	0.0576 (6)	0.0579 (7)	0.0580 (7)	−0.0021 (5)	−0.0261 (5)	−0.0220 (5)
O3	0.0563 (8)	0.1470 (15)	0.0704 (9)	0.0362 (9)	−0.0318 (7)	−0.0335 (9)
S1	0.04034 (17)	0.0485 (2)	0.03049 (16)	0.00304 (14)	−0.01514 (13)	−0.00580 (13)
S2	0.04688 (19)	0.0454 (2)	0.03417 (17)	0.01400 (14)	−0.01465 (14)	−0.00459 (14)

C1—C2	1.3834 (19)	C12—S1	1.7496 (13)
C1—C6	1.3949 (18)	C13—C14	1.382 (2)
C1—N1	1.4226 (18)	C13—H13	0.9300
C2—C3	1.376 (2)	C14—C15	1.368 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.385 (3)	C15—C16	1.370 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.375 (2)	C16—C17	1.369 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.386 (2)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.3840 (18)
C6—C7	1.4439 (19)	C18—C23	1.3885 (17)
C7—C8	1.3543 (18)	C18—S2	1.7727 (13)
C7—S2	1.7477 (12)	C19—C20	1.382 (2)
C8—N1	1.4332 (16)	C19—H19	0.9300
C8—C9	1.4930 (19)	C20—C21	1.374 (2)
C9—N2	1.4482 (17)	C20—H20	0.9300
C9—H9A	0.9700	C21—C22	1.375 (2)
C9—H9B	0.9700	C21—H21	0.9300
C10—O3	1.2093 (19)	C22—C23	1.379 (2)
C10—N2	1.3368 (18)	C22—H22	0.9300
C10—C11	1.500 (2)	C23—H23	0.9300
C11—H11A	0.9600	N1—S1	1.6789 (11)
C11—H11B	0.9600	N2—H2A	0.8600
C11—H11C	0.9600	O1—S1	1.4193 (11)
C12—C13	1.382 (2)	O2—S1	1.4198 (12)
C12—C17	1.382 (2)
C2—C1—C6	121.75 (14)	C14—C13—H13	120.7
C2—C1—N1	130.00 (13)	C15—C14—C13	120.14 (16)
C6—C1—N1	108.02 (11)	C15—C14—H14	119.9
C3—C2—C1	116.88 (15)	C13—C14—H14	119.9
C3—C2—H2	121.6	C14—C15—C16	120.71 (16)
C1—C2—H2	121.6	C14—C15—H15	119.6
C2—C3—C4	122.07 (15)	C16—C15—H15	119.6
C2—C3—H3	119.0	C17—C16—C15	120.32 (17)
C4—C3—H3	119.0	C17—C16—H16	119.8
C5—C4—C3	120.89 (16)	C15—C16—H16	119.8
C5—C4—H4	119.6	C16—C17—C12	119.01 (16)
C3—C4—H4	119.6	C16—C17—H17	120.5
C4—C5—C6	118.11 (15)	C12—C17—H17	120.5
C4—C5—H5	120.9	C19—C18—C23	119.60 (13)
C6—C5—H5	120.9	C19—C18—S2	123.85 (10)
C5—C6—C1	120.29 (13)	C23—C18—S2	116.52 (10)
C5—C6—C7	132.35 (13)	C20—C19—C18	119.66 (13)
C1—C6—C7	107.20 (12)	C20—C19—H19	120.2
C8—C7—C6	109.04 (11)	C18—C19—H19	120.2
C8—C7—S2	125.89 (11)	C21—C20—C19	120.68 (15)
C6—C7—S2	125.02 (10)	C21—C20—H20	119.7
C7—C8—N1	108.48 (11)	C19—C20—H20	119.7
C7—C8—C9	128.32 (12)	C20—C21—C22	119.72 (14)
N1—C8—C9	122.13 (11)	C20—C21—H21	120.1
N2—C9—C8	110.29 (11)	C22—C21—H21	120.1
N2—C9—H9A	109.6	C21—C22—C23	120.40 (14)
C8—C9—H9A	109.6	C21—C22—H22	119.8
N2—C9—H9B	109.6	C23—C22—H22	119.8
C8—C9—H9B	109.6	C22—C23—C18	119.92 (13)
H9A—C9—H9B	108.1	C22—C23—H23	120.0
O3—C10—N2	121.55 (15)	C18—C23—H23	120.0
O3—C10—C11	122.30 (15)	C1—N1—C8	107.23 (10)
N2—C10—C11	116.11 (14)	C1—N1—S1	119.17 (9)
C10—C11—H11A	109.5	C8—N1—S1	118.64 (9)
C10—C11—H11B	109.5	C10—N2—C9	121.31 (12)
H11A—C11—H11B	109.5	C10—N2—H2A	119.3
C10—C11—H11C	109.5	C9—N2—H2A	119.3
H11A—C11—H11C	109.5	O1—S1—O2	119.66 (7)
H11B—C11—H11C	109.5	O1—S1—N1	106.41 (7)
C13—C12—C17	121.18 (14)	O2—S1—N1	106.61 (6)
C13—C12—S1	120.19 (11)	O1—S1—C12	108.97 (7)
C17—C12—S1	118.52 (12)	O2—S1—C12	110.17 (7)
C12—C13—C14	118.64 (15)	N1—S1—C12	103.77 (6)
C12—C13—H13	120.7	C7—S2—C18	101.32 (6)
C6—C1—C2—C3	−0.2 (2)	C19—C20—C21—C22	−0.9 (3)
N1—C1—C2—C3	173.51 (14)	C20—C21—C22—C23	0.3 (3)
C1—C2—C3—C4	−0.6 (2)	C21—C22—C23—C18	0.5 (2)
C2—C3—C4—C5	1.0 (3)	C19—C18—C23—C22	−0.8 (2)
C3—C4—C5—C6	−0.5 (2)	S2—C18—C23—C22	177.16 (12)
C4—C5—C6—C1	−0.3 (2)	C2—C1—N1—C8	−175.59 (13)
C4—C5—C6—C7	−175.17 (14)	C6—C1—N1—C8	−1.19 (13)
C2—C1—C6—C5	0.7 (2)	C2—C1—N1—S1	46.01 (18)
N1—C1—C6—C5	−174.30 (12)	C6—C1—N1—S1	−139.59 (9)
C2—C1—C6—C7	176.72 (12)	C7—C8—N1—C1	0.11 (13)
N1—C1—C6—C7	1.76 (14)	C9—C8—N1—C1	169.22 (11)
C5—C6—C7—C8	173.66 (14)	C7—C8—N1—S1	138.76 (10)
C1—C6—C7—C8	−1.72 (14)	C9—C8—N1—S1	−52.12 (14)
C5—C6—C7—S2	−3.8 (2)	O3—C10—N2—C9	−5.2 (3)
C1—C6—C7—S2	−179.22 (9)	C11—C10—N2—C9	172.65 (14)
C6—C7—C8—N1	0.98 (14)	C8—C9—N2—C10	−83.42 (16)
S2—C7—C8—N1	178.45 (9)	C1—N1—S1—O1	−43.85 (11)
C6—C7—C8—C9	−167.25 (12)	C8—N1—S1—O1	−177.59 (10)
S2—C7—C8—C9	10.2 (2)	C1—N1—S1—O2	−172.62 (10)
C7—C8—C9—N2	104.47 (15)	C8—N1—S1—O2	53.64 (11)
N1—C8—C9—N2	−62.33 (15)	C1—N1—S1—C12	71.05 (10)
C17—C12—C13—C14	0.4 (2)	C8—N1—S1—C12	−62.69 (11)
S1—C12—C13—C14	−175.91 (12)	C13—C12—S1—O1	−156.18 (11)
C12—C13—C14—C15	−0.2 (2)	C17—C12—S1—O1	27.46 (13)
C13—C14—C15—C16	−0.2 (3)	C13—C12—S1—O2	−23.05 (13)
C14—C15—C16—C17	0.4 (3)	C17—C12—S1—O2	160.59 (12)
C15—C16—C17—C12	−0.2 (3)	C13—C12—S1—N1	90.75 (12)
C13—C12—C17—C16	−0.2 (2)	C17—C12—S1—N1	−85.61 (12)
S1—C12—C17—C16	176.18 (14)	C8—C7—S2—C18	108.39 (12)
C23—C18—C19—C20	0.2 (2)	C6—C7—S2—C18	−74.53 (12)
S2—C18—C19—C20	−177.54 (12)	C19—C18—S2—C7	−15.37 (14)
C18—C19—C20—C21	0.6 (2)	C23—C18—S2—C7	166.79 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.48	3.3179 (15)	165
C21—H21···O1ii	0.93	2.44	3.2666 (18)	149
C5—H5···Cg3iii	0.93	2.94	3.7634 (18)	149
C9—H9A···Cg4iv	0.97	2.95	3.5792 (16)	124
C11—H11A···Cg2v	0.96	2.91	3.5974 (21)	129
C16—H16···Cg4vi	0.93	2.95	3.7453 (21)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.48	3.3179 (15)	165
C21—H21⋯O1ii	0.93	2.44	3.2666 (18)	149
C5—H5⋯Cg3iii	0.93	2.94	3.7634 (18)	149
C9—H9A⋯Cg4iv	0.97	2.95	3.5792 (16)	124
C11—H11A⋯Cg2v	0.96	2.91	3.5974 (21)	129
C16—H16⋯Cg4vi	0.93	2.95	3.7453 (21)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C12–C17 and C18–C23 rings, respectively.