N-[(3-Phenyl-sulfanyl-1-phenyl-sulfonyl-1H-indol-2-yl)meth-yl]propionamide.

In the title compound, C(24)H(22)N(2)O(3)S(2), the phenyl rings form dihedral angles of 75.2 (1) and 86.1 (1)° with the indole ring system. The mol-ecular structure is stabilized by intra-molecular C-H⋯O and N-H⋯O hydrogen bonds. The crystal structure exhibit inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, C-H⋯π and π-π [centroid-centroid distance = 3.748 (1) Å] inter-actions.

Related literature

For the biological activity of indole derivatives, see: Nieto et al. (2005 ▶); Olgen & Coban (2003 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C24H22N2O3S2

M = 450.56

Monoclinic,

a = 10.9216 (3) Å

b = 23.1856 (6) Å

c = 9.4298 (2) Å

β = 110.147 (1)°

V = 2241.74 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 295 K

0.26 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.959

26619 measured reflections

5543 independent reflections

3962 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.04

5543 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041518/gw2070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041518/gw2070Isup2.hkl

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

C24H22N2O3S2	F(000) = 944
Mr = 450.56	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9917 reflections
a = 10.9216 (3) Å	θ = 2.5–27.5°
b = 23.1856 (6) Å	µ = 0.27 mm−1
c = 9.4298 (2) Å	T = 295 K
β = 110.147 (1)°	Block, colourless
V = 2241.74 (10) Å3	0.26 × 0.20 × 0.16 mm
Z = 4

Bruker Kappa APEXII diffractometer	5543 independent reflections
Radiation source: fine-focus sealed tube	3962 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.934, Tmax = 0.959	k = −30→30
26619 measured reflections	l = −12→12

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) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.7649P] where P = (Fo2 + 2Fc2)/3
5543 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.35657 (17)	0.09160 (9)	0.2609 (2)	0.0566 (5)
C2	0.3938 (2)	0.03731 (10)	0.3194 (3)	0.0700 (6)
H2	0.3548	0.0203	0.3824	0.084*
C3	0.4893 (2)	0.00865 (12)	0.2834 (3)	0.0863 (8)
H3	0.5157	−0.0279	0.3226	0.104*
C4	0.5455 (2)	0.03392 (15)	0.1901 (4)	0.0951 (9)
H4	0.6101	0.0144	0.1660	0.114*
C5	0.5080 (3)	0.08729 (16)	0.1321 (4)	0.1013 (9)
H5	0.5466	0.1039	0.0683	0.122*
C6	0.4135 (2)	0.11678 (12)	0.1672 (3)	0.0823 (7)
H6	0.3882	0.1534	0.1280	0.099*
C7	0.02638 (16)	0.12894 (7)	0.03684 (18)	0.0424 (4)
C8	−0.08307 (16)	0.09744 (7)	−0.02800 (17)	0.0408 (4)
C9	−0.08564 (16)	0.05099 (7)	0.07163 (18)	0.0400 (4)
C10	−0.17279 (18)	0.00610 (8)	0.0598 (2)	0.0505 (4)
H10	−0.2475	0.0026	−0.0252	0.061*
C11	−0.1468 (2)	−0.03292 (9)	0.1756 (3)	0.0603 (5)
H11	−0.2040	−0.0633	0.1690	0.072*
C12	−0.0360 (2)	−0.02736 (9)	0.3024 (2)	0.0621 (5)
H12	−0.0205	−0.0543	0.3798	0.075*
C13	0.0514 (2)	0.01642 (9)	0.3174 (2)	0.0562 (5)
H13	0.1255	0.0197	0.4033	0.067*
C14	0.02547 (16)	0.05580 (7)	0.19997 (18)	0.0421 (4)
C15	−0.31688 (17)	0.15356 (8)	−0.1635 (2)	0.0486 (4)
C16	−0.2896 (2)	0.18462 (9)	−0.0313 (2)	0.0581 (5)
H16	−0.2073	0.1826	0.0426	0.070*
C17	−0.3848 (3)	0.21854 (11)	−0.0095 (3)	0.0791 (7)
H17	−0.3663	0.2396	0.0794	0.095*
C18	−0.5068 (3)	0.22168 (13)	−0.1175 (4)	0.0935 (9)
H18	−0.5709	0.2444	−0.1013	0.112*
C19	−0.5334 (2)	0.19155 (13)	−0.2483 (4)	0.0920 (8)
H19	−0.6156	0.1942	−0.3222	0.110*
C20	−0.4396 (2)	0.15706 (10)	−0.2721 (3)	0.0703 (6)
H20	−0.4589	0.1361	−0.3613	0.084*
C21	0.0691 (2)	0.18028 (8)	−0.0289 (2)	0.0523 (4)
H21A	0.1634	0.1802	0.0017	0.063*
H21B	0.0340	0.1777	−0.1382	0.063*
C22	−0.0289 (2)	0.27564 (8)	−0.0787 (2)	0.0547 (5)
C23	−0.0686 (3)	0.32715 (9)	−0.0106 (2)	0.0770 (7)
H23A	−0.0868	0.3150	0.0786	0.092*
H23B	0.0043	0.3538	0.0219	0.092*
C24	−0.1833 (3)	0.35801 (12)	−0.1114 (3)	0.0908 (8)
H24A	−0.1677	0.3693	−0.2016	0.136*
H24B	−0.1990	0.3917	−0.0610	0.136*
H24C	−0.2581	0.3331	−0.1374	0.136*
N1	0.09434 (14)	0.10500 (6)	0.17978 (16)	0.0455 (3)
N2	0.02720 (17)	0.23387 (6)	0.01795 (16)	0.0538 (4)
H2A	0.0391	0.2389	0.1121	0.065*
O1	0.23581 (16)	0.10952 (8)	0.44854 (16)	0.0793 (5)
O2	0.24265 (16)	0.18788 (7)	0.2755 (2)	0.0806 (5)
O3	−0.04305 (18)	0.27293 (7)	−0.21278 (15)	0.0766 (5)
S1	0.23448 (5)	0.12841 (2)	0.30516 (6)	0.05906 (16)
S2	−0.20032 (5)	0.10989 (2)	−0.20547 (5)	0.05258 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0413 (9)	0.0629 (12)	0.0571 (11)	−0.0080 (8)	0.0062 (8)	−0.0097 (9)
C2	0.0551 (12)	0.0777 (15)	0.0703 (14)	0.0019 (11)	0.0128 (10)	0.0042 (11)
C3	0.0606 (14)	0.0838 (18)	0.105 (2)	0.0139 (13)	0.0163 (14)	−0.0022 (15)
C4	0.0519 (13)	0.119 (2)	0.117 (2)	0.0048 (15)	0.0318 (15)	−0.0191 (19)
C5	0.0679 (16)	0.122 (3)	0.128 (3)	−0.0041 (16)	0.0524 (17)	0.011 (2)
C6	0.0575 (13)	0.0840 (17)	0.108 (2)	−0.0058 (12)	0.0320 (14)	0.0118 (14)
C7	0.0488 (9)	0.0427 (9)	0.0380 (8)	0.0025 (7)	0.0179 (7)	−0.0070 (7)
C8	0.0447 (9)	0.0437 (9)	0.0352 (8)	0.0051 (7)	0.0150 (7)	−0.0045 (7)
C9	0.0434 (8)	0.0399 (8)	0.0405 (8)	0.0062 (7)	0.0194 (7)	−0.0052 (6)
C10	0.0478 (9)	0.0498 (10)	0.0569 (10)	−0.0007 (8)	0.0219 (8)	−0.0082 (8)
C11	0.0690 (13)	0.0462 (11)	0.0784 (14)	0.0009 (9)	0.0418 (11)	0.0024 (10)
C12	0.0798 (14)	0.0528 (11)	0.0636 (12)	0.0179 (10)	0.0373 (11)	0.0167 (9)
C13	0.0605 (11)	0.0618 (12)	0.0454 (10)	0.0146 (9)	0.0169 (8)	0.0075 (8)
C14	0.0443 (9)	0.0442 (9)	0.0400 (8)	0.0073 (7)	0.0172 (7)	−0.0042 (7)
C15	0.0503 (9)	0.0453 (10)	0.0469 (9)	0.0041 (8)	0.0128 (8)	0.0105 (8)
C16	0.0581 (11)	0.0572 (12)	0.0567 (11)	0.0122 (9)	0.0169 (9)	0.0004 (9)
C17	0.0856 (16)	0.0702 (15)	0.0843 (16)	0.0264 (13)	0.0331 (14)	0.0003 (12)
C18	0.0784 (17)	0.0898 (19)	0.114 (2)	0.0439 (15)	0.0348 (17)	0.0238 (17)
C19	0.0615 (14)	0.099 (2)	0.099 (2)	0.0263 (14)	0.0062 (14)	0.0286 (17)
C20	0.0635 (13)	0.0708 (14)	0.0622 (13)	0.0088 (11)	0.0034 (10)	0.0099 (11)
C21	0.0637 (11)	0.0505 (10)	0.0496 (10)	−0.0055 (9)	0.0284 (9)	−0.0068 (8)
C22	0.0824 (14)	0.0484 (10)	0.0374 (9)	−0.0075 (9)	0.0258 (9)	−0.0033 (8)
C23	0.130 (2)	0.0541 (12)	0.0471 (11)	0.0132 (13)	0.0308 (13)	−0.0022 (9)
C24	0.119 (2)	0.0855 (18)	0.0672 (15)	0.0240 (16)	0.0306 (15)	0.0015 (13)
N1	0.0438 (7)	0.0509 (8)	0.0388 (7)	−0.0017 (6)	0.0102 (6)	−0.0052 (6)
N2	0.0867 (12)	0.0439 (8)	0.0348 (7)	−0.0055 (8)	0.0259 (8)	−0.0049 (6)
O1	0.0732 (10)	0.1127 (13)	0.0419 (8)	0.0004 (9)	0.0070 (7)	−0.0195 (8)
O2	0.0718 (10)	0.0555 (9)	0.0969 (12)	−0.0100 (7)	0.0064 (9)	−0.0252 (8)
O3	0.1285 (14)	0.0722 (10)	0.0369 (7)	0.0096 (9)	0.0383 (8)	0.0020 (6)
S1	0.0518 (3)	0.0646 (3)	0.0511 (3)	−0.0045 (2)	0.0054 (2)	−0.0177 (2)
S2	0.0570 (3)	0.0629 (3)	0.0337 (2)	0.0058 (2)	0.01022 (18)	−0.00357 (19)

C1—C6	1.374 (3)	C15—C16	1.380 (3)
C1—C2	1.378 (3)	C15—C20	1.381 (3)
C1—S1	1.750 (2)	C15—S2	1.7748 (19)
C2—C3	1.374 (3)	C16—C17	1.374 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.366 (4)	C17—C18	1.372 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.358 (4)	C18—C19	1.358 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.370 (4)	C19—C20	1.378 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.354 (2)	C21—N2	1.445 (2)
C7—N1	1.410 (2)	C21—H21A	0.9700
C7—C21	1.489 (3)	C21—H21B	0.9700
C8—C9	1.436 (2)	C22—O3	1.222 (2)
C8—S2	1.7457 (16)	C22—N2	1.326 (2)
C9—C10	1.389 (2)	C22—C23	1.489 (3)
C9—C14	1.392 (2)	C23—C24	1.472 (3)
C10—C11	1.370 (3)	C23—H23A	0.9700
C10—H10	0.9300	C23—H23B	0.9700
C11—C12	1.383 (3)	C24—H24A	0.9600
C11—H11	0.9300	C24—H24B	0.9600
C12—C13	1.367 (3)	C24—H24C	0.9600
C12—H12	0.9300	N1—S1	1.6699 (14)
C13—C14	1.388 (2)	N2—H2A	0.8600
C13—H13	0.9300	O1—S1	1.4165 (17)
C14—N1	1.415 (2)	O2—S1	1.4159 (17)
C6—C1—C2	120.6 (2)	C15—C16—H16	120.2
C6—C1—S1	119.78 (18)	C18—C17—C16	120.7 (2)
C2—C1—S1	119.61 (18)	C18—C17—H17	119.7
C3—C2—C1	119.2 (2)	C16—C17—H17	119.7
C3—C2—H2	120.4	C19—C18—C17	119.8 (2)
C1—C2—H2	120.4	C19—C18—H18	120.1
C4—C3—C2	120.0 (3)	C17—C18—H18	120.1
C4—C3—H3	120.0	C18—C19—C20	120.5 (2)
C2—C3—H3	120.0	C18—C19—H19	119.7
C5—C4—C3	120.6 (3)	C20—C19—H19	119.7
C5—C4—H4	119.7	C19—C20—C15	120.0 (2)
C3—C4—H4	119.7	C19—C20—H20	120.0
C4—C5—C6	120.4 (3)	C15—C20—H20	120.0
C4—C5—H5	119.8	N2—C21—C7	112.51 (15)
C6—C5—H5	119.8	N2—C21—H21A	109.1
C5—C6—C1	119.2 (3)	C7—C21—H21A	109.1
C5—C6—H6	120.4	N2—C21—H21B	109.1
C1—C6—H6	120.4	C7—C21—H21B	109.1
C8—C7—N1	108.15 (15)	H21A—C21—H21B	107.8
C8—C7—C21	126.70 (16)	O3—C22—N2	122.52 (18)
N1—C7—C21	125.15 (15)	O3—C22—C23	122.38 (18)
C7—C8—C9	108.81 (14)	N2—C22—C23	115.06 (16)
C7—C8—S2	125.86 (14)	C24—C23—C22	114.89 (19)
C9—C8—S2	125.31 (13)	C24—C23—H23A	108.5
C10—C9—C14	119.86 (16)	C22—C23—H23A	108.5
C10—C9—C8	132.61 (16)	C24—C23—H23B	108.5
C14—C9—C8	107.52 (15)	C22—C23—H23B	108.5
C11—C10—C9	118.87 (18)	H23A—C23—H23B	107.5
C11—C10—H10	120.6	C23—C24—H24A	109.5
C9—C10—H10	120.6	C23—C24—H24B	109.5
C10—C11—C12	120.43 (19)	H24A—C24—H24B	109.5
C10—C11—H11	119.8	C23—C24—H24C	109.5
C12—C11—H11	119.8	H24A—C24—H24C	109.5
C13—C12—C11	122.05 (18)	H24B—C24—H24C	109.5
C13—C12—H12	119.0	C7—N1—C14	108.48 (13)
C11—C12—H12	119.0	C7—N1—S1	126.97 (12)
C12—C13—C14	117.57 (18)	C14—N1—S1	124.54 (12)
C12—C13—H13	121.2	C22—N2—C21	122.54 (15)
C14—C13—H13	121.2	C22—N2—H2A	118.7
C13—C14—C9	121.21 (17)	C21—N2—H2A	118.7
C13—C14—N1	131.79 (16)	O2—S1—O1	120.59 (11)
C9—C14—N1	107.00 (14)	O2—S1—N1	106.35 (9)
C16—C15—C20	119.43 (19)	O1—S1—N1	106.31 (9)
C16—C15—S2	123.45 (14)	O2—S1—C1	108.84 (11)
C20—C15—S2	117.10 (16)	O1—S1—C1	108.57 (10)
C17—C16—C15	119.7 (2)	N1—S1—C1	105.10 (8)
C17—C16—H16	120.2	C8—S2—C15	103.06 (8)
C6—C1—C2—C3	0.3 (3)	C16—C15—C20—C19	0.3 (3)
S1—C1—C2—C3	179.69 (18)	S2—C15—C20—C19	−178.15 (19)
C1—C2—C3—C4	−0.4 (4)	C8—C7—C21—N2	93.9 (2)
C2—C3—C4—C5	0.0 (4)	N1—C7—C21—N2	−85.7 (2)
C3—C4—C5—C6	0.4 (5)	O3—C22—C23—C24	32.6 (4)
C4—C5—C6—C1	−0.4 (5)	N2—C22—C23—C24	−149.7 (2)
C2—C1—C6—C5	0.0 (4)	C8—C7—N1—C14	2.10 (18)
S1—C1—C6—C5	−179.3 (2)	C21—C7—N1—C14	−178.23 (15)
N1—C7—C8—C9	−1.67 (18)	C8—C7—N1—S1	−179.39 (12)
C21—C7—C8—C9	178.66 (16)	C21—C7—N1—S1	0.3 (2)
N1—C7—C8—S2	179.76 (12)	C13—C14—N1—C7	178.38 (18)
C21—C7—C8—S2	0.1 (3)	C9—C14—N1—C7	−1.68 (17)
C7—C8—C9—C10	−178.64 (17)	C13—C14—N1—S1	−0.2 (3)
S2—C8—C9—C10	−0.1 (3)	C9—C14—N1—S1	179.76 (12)
C7—C8—C9—C14	0.63 (18)	O3—C22—N2—C21	−3.8 (3)
S2—C8—C9—C14	179.21 (12)	C23—C22—N2—C21	178.51 (19)
C14—C9—C10—C11	−0.3 (2)	C7—C21—N2—C22	−132.61 (19)
C8—C9—C10—C11	178.90 (17)	C7—N1—S1—O2	25.25 (18)
C9—C10—C11—C12	0.4 (3)	C14—N1—S1—O2	−156.46 (14)
C10—C11—C12—C13	−0.2 (3)	C7—N1—S1—O1	154.92 (15)
C11—C12—C13—C14	−0.1 (3)	C14—N1—S1—O1	−26.79 (16)
C12—C13—C14—C9	0.2 (3)	C7—N1—S1—C1	−90.08 (16)
C12—C13—C14—N1	−179.87 (18)	C14—N1—S1—C1	88.21 (15)
C10—C9—C14—C13	0.0 (2)	C6—C1—S1—O2	−19.4 (2)
C8—C9—C14—C13	−179.39 (15)	C2—C1—S1—O2	161.21 (16)
C10—C9—C14—N1	−179.96 (14)	C6—C1—S1—O1	−152.42 (18)
C8—C9—C14—N1	0.66 (17)	C2—C1—S1—O1	28.22 (19)
C20—C15—C16—C17	0.0 (3)	C6—C1—S1—N1	94.15 (19)
S2—C15—C16—C17	178.35 (17)	C2—C1—S1—N1	−85.20 (17)
C15—C16—C17—C18	0.2 (4)	C7—C8—S2—C15	−93.53 (16)
C16—C17—C18—C19	−0.8 (4)	C9—C8—S2—C15	88.13 (15)
C17—C18—C19—C20	1.1 (5)	C16—C15—S2—C8	20.21 (18)
C18—C19—C20—C15	−0.9 (4)	C20—C15—S2—C8	−161.43 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.52	2.939 (2)	111
C6—H6···O2	0.93	2.57	2.925 (3)	103
C13—H13···O1	0.93	2.37	2.921 (3)	118
C21—H21A···O2	0.97	2.43	2.849 (3)	106
C21—H21B···O3	0.97	2.38	2.767 (2)	103
C18—H18···O2i	0.93	2.52	3.317 (3)	144
N2—H2A···O3ii	0.86	2.15	2.899 (2)	145
C16—H16···O3ii	0.93	2.60	3.416 (3)	147
C10—H10···Cg2iii	0.93	2.81	3.658 (2)	152
C5—H5···Cg4iv	0.93	2.91	3.788 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.86	2.52	2.939 (2)	111
C13—H13⋯O1	0.93	2.37	2.921 (3)	118
C18—H18⋯O2i	0.93	2.52	3.317 (3)	144
N2—H2A⋯O3ii	0.86	2.15	2.899 (2)	145
C16—H16⋯O3ii	0.93	2.60	3.416 (3)	147
C10—H10⋯Cg2iii	0.93	2.81	3.658 (2)	152
C5—H5⋯Cg4iv	0.93	2.91	3.788 (4)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 and Cg4 are the centroids of C1–C6 and C15–C20 rings, respectively.