1,2-Bis(1-phenyl­sulfonyl-3-phenyl­thio­indol-2-yl)­ethane

In the title compound, C₄₂H₃₂N₂O₄S₄, the dihedral angle between the fused rings is 1.4 (1)°. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 75.7 (1)° and the phenyl ring attached to the sulfide S atom makes a dihedral angle of 70.6 (1)° with the best plane of the indole ring. The molecular structure is stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.144
• Data-to-parameter ratio = 19.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983, 1995).

1,2-Bis(1'-Phenylsulfonyl-3-phenylthioindole-2-yl)ethane

Crystal data

C42H32N2O4S4	F(000) = 788
Mr = 756.94	Dx = 1.318 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.5439 (4) Å	Cell parameters from 13390 reflections
b = 8.3686 (2) Å	θ = 1.7–28.3°
c = 18.9898 (6) Å	µ = 0.29 mm^−1
β = 106.881 (1)°	T = 293 K
V = 1907.55 (10) Å^3	Needle, colourless
Z = 2	0.46 × 0.16 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2139 reflections with I > 2σa(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
Graphite monochromator	θmax = 28.3°, θmin = 1.7°
ω scans	h = −13→16
12921 measured reflections	k = −10→11
4615 independent reflections	l = −24→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0499P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
4615 reflections	Δρmax = 0.24 e Å^−3
236 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (8)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.29178 (6)	0.55196 (9)	0.04830 (5)	0.0586 (3)
S2	−0.07563 (6)	0.76266 (10)	−0.16165 (5)	0.0645 (3)
N1	0.20069 (16)	0.5642 (2)	−0.03547 (12)	0.0420 (6)
O1	0.38114 (17)	0.4551 (2)	0.04055 (14)	0.0829 (8)
O2	0.23027 (19)	0.5045 (3)	0.09667 (12)	0.0828 (8)
C1	0.0170 (2)	0.5885 (3)	0.00010 (14)	0.0429 (7)
H1A	−0.0497	0.6537	−0.0155	0.051*
H1B	0.0573	0.6197	0.0499	0.051*
C2	0.0879 (2)	0.6209 (3)	−0.04908 (14)	0.0392 (6)
C3	0.0575 (2)	0.6885 (3)	−0.11646 (15)	0.0428 (7)
C4	0.1481 (2)	0.6820 (3)	−0.14851 (15)	0.0459 (7)
C5	0.1604 (3)	0.7321 (4)	−0.21518 (19)	0.0723 (10)
H5	0.1015	0.7808	−0.2500	0.087*
C6	0.2603 (4)	0.7089 (5)	−0.2293 (2)	0.0881 (12)
H6	0.2690	0.7423	−0.2741	0.106*
C7	0.3480 (3)	0.6370 (5)	−0.1783 (2)	0.0834 (12)
H7	0.4150	0.6226	−0.1892	0.100*
C8	0.3388 (3)	0.5856 (4)	−0.1114 (2)	0.0663 (9)
H8	0.3986	0.5380	−0.0769	0.080*
C9	0.2370 (2)	0.6075 (3)	−0.09721 (15)	0.0440 (7)
C10	0.3400 (2)	0.7488 (4)	0.06822 (16)	0.0543 (8)
C11	0.4469 (3)	0.7877 (4)	0.0712 (2)	0.0890 (12)
H11	0.4952	0.7100	0.0632	0.107*
C12	0.4831 (4)	0.9437 (5)	0.0862 (3)	0.1051 (15)
H12	0.5568	0.9697	0.0907	0.126*
C13	0.4118 (4)	1.0582 (5)	0.0943 (2)	0.0965 (13)
H13	0.4366	1.1630	0.1036	0.116*
C14	0.3047 (4)	1.0221 (5)	0.0890 (3)	0.1148 (17)
H14	0.2558	1.1023	0.0935	0.138*
C15	0.2682 (3)	0.8669 (5)	0.0770 (2)	0.0937 (13)
H15	0.1951	0.8415	0.0749	0.112*
C16	−0.0470 (2)	0.9670 (3)	−0.17332 (16)	0.0478 (7)
C17	−0.1249 (3)	1.0488 (4)	−0.22860 (17)	0.0619 (9)
H17	−0.1873	0.9956	−0.2577	0.074*
C18	−0.1101 (3)	1.2062 (5)	−0.2403 (2)	0.0765 (11)
H18	−0.1632	1.2598	−0.2772	0.092*
C19	−0.0196 (4)	1.2866 (4)	−0.1994 (2)	0.0762 (11)
H19	−0.0106	1.3942	−0.2086	0.091*
C20	0.0590 (3)	1.2085 (4)	−0.14413 (19)	0.0681 (10)
H20	0.1216	1.2629	−0.1160	0.082*
C21	0.0443 (3)	1.0487 (4)	−0.13063 (17)	0.0572 (8)
H21	0.0963	0.9963	−0.0926	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0399 (4)	0.0639 (5)	0.0651 (6)	−0.0055 (4)	0.0044 (4)	0.0225 (4)
S2	0.0329 (4)	0.0706 (6)	0.0842 (7)	−0.0022 (4)	0.0078 (4)	0.0246 (4)
N1	0.0277 (12)	0.0516 (13)	0.0493 (15)	0.0022 (10)	0.0153 (10)	0.0093 (10)
O1	0.0448 (13)	0.0562 (14)	0.132 (2)	0.0123 (10)	0.0006 (13)	0.0232 (12)
O2	0.0637 (15)	0.117 (2)	0.0599 (15)	−0.0268 (14)	0.0062 (12)	0.0407 (13)
C1	0.0381 (15)	0.0519 (16)	0.0469 (18)	−0.0035 (12)	0.0255 (13)	0.0030 (13)
C2	0.0326 (14)	0.0421 (15)	0.0467 (18)	−0.0016 (11)	0.0174 (12)	0.0013 (13)
C3	0.0326 (15)	0.0505 (16)	0.0478 (18)	−0.0013 (12)	0.0156 (13)	0.0117 (13)
C4	0.0431 (17)	0.0559 (18)	0.0464 (19)	−0.0040 (13)	0.0253 (14)	0.0024 (13)
C5	0.073 (3)	0.097 (3)	0.057 (2)	−0.0094 (19)	0.0347 (19)	0.0129 (18)
C6	0.098 (3)	0.117 (3)	0.076 (3)	−0.016 (3)	0.067 (3)	0.002 (2)
C7	0.077 (3)	0.095 (3)	0.109 (3)	−0.010 (2)	0.077 (3)	−0.010 (2)
C8	0.0464 (19)	0.068 (2)	0.099 (3)	0.0030 (15)	0.0431 (18)	−0.0021 (18)
C9	0.0375 (16)	0.0462 (16)	0.058 (2)	−0.0027 (12)	0.0285 (14)	−0.0015 (13)
C10	0.0414 (17)	0.0652 (19)	0.053 (2)	−0.0086 (15)	0.0090 (14)	0.0026 (15)
C11	0.053 (2)	0.061 (2)	0.158 (4)	−0.0032 (17)	0.038 (2)	0.006 (2)
C12	0.075 (3)	0.074 (3)	0.174 (5)	−0.023 (2)	0.048 (3)	−0.009 (3)
C13	0.104 (4)	0.078 (3)	0.113 (4)	−0.019 (3)	0.040 (3)	−0.027 (2)
C14	0.089 (3)	0.101 (3)	0.155 (4)	−0.008 (3)	0.038 (3)	−0.071 (3)
C15	0.065 (3)	0.113 (3)	0.111 (3)	−0.023 (2)	0.040 (2)	−0.059 (3)
C16	0.0392 (16)	0.0611 (19)	0.0481 (19)	0.0054 (14)	0.0207 (14)	0.0070 (14)
C17	0.0508 (19)	0.079 (2)	0.058 (2)	0.0080 (16)	0.0191 (16)	0.0210 (17)
C18	0.083 (3)	0.076 (3)	0.079 (3)	0.018 (2)	0.038 (2)	0.024 (2)
C19	0.109 (3)	0.056 (2)	0.089 (3)	0.015 (2)	0.069 (3)	0.009 (2)
C20	0.075 (3)	0.068 (2)	0.074 (3)	−0.0080 (19)	0.041 (2)	−0.0204 (18)
C21	0.056 (2)	0.068 (2)	0.052 (2)	0.0036 (16)	0.0233 (16)	−0.0004 (15)

Geometric parameters (Å, º)

S1—O2	1.417 (2)	C8—H8	0.9300
S1—O1	1.425 (2)	C10—C11	1.365 (4)
S1—N1	1.671 (2)	C10—C15	1.380 (5)
S1—C10	1.758 (3)	C11—C12	1.384 (5)
S2—C3	1.754 (3)	C11—H11	0.9300
S2—C16	1.774 (3)	C12—C13	1.349 (5)
N1—C9	1.423 (3)	C12—H12	0.9300
N1—C2	1.442 (3)	C13—C14	1.352 (5)
C1—C2	1.490 (3)	C13—H13	0.9300
C1—C1^i	1.542 (5)	C14—C15	1.374 (5)
C1—H1A	0.9700	C14—H14	0.9300
C1—H1B	0.9700	C15—H15	0.9300
C2—C3	1.349 (3)	C16—C21	1.378 (4)
C3—C4	1.438 (4)	C16—C17	1.389 (4)
C4—C5	1.384 (4)	C17—C18	1.357 (4)
C4—C9	1.397 (4)	C17—H17	0.9300
C5—C6	1.371 (5)	C18—C19	1.353 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.375 (5)	C19—C20	1.379 (5)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.378 (5)	C20—C21	1.384 (4)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.391 (4)	C21—H21	0.9300
O2—S1—O1	120.01 (15)	C8—C9—N1	131.1 (3)
O2—S1—N1	106.5 (1)	C4—C9—N1	107.8 (2)
O1—S1—N1	106.1 (1)	C11—C10—C15	119.5 (3)
O2—S1—C10	110.0 (2)	C11—C10—S1	120.4 (3)
O1—S1—C10	108.8 (1)	C15—C10—S1	120.1 (3)
N1—S1—C10	104.2 (1)	C10—C11—C12	119.5 (4)
C3—S2—C16	101.75 (13)	C10—C11—H11	120.2
C9—N1—C2	107.5 (2)	C12—C11—H11	120.2
C9—N1—S1	120.41 (18)	C13—C12—C11	120.3 (4)
C2—N1—S1	123.7 (2)	C13—C12—H12	119.8
C2—C1—C1^i	112.9 (3)	C11—C12—H12	119.8
C2—C1—H1A	109.0	C14—C13—C12	120.7 (4)
C1^i—C1—H1A	109.0	C14—C13—H13	119.7
C2—C1—H1B	109.0	C12—C13—H13	119.7
C1^i—C1—H1B	109.0	C13—C14—C15	120.0 (4)
H1A—C1—H1B	107.8	C13—C14—H14	120.0
C3—C2—N1	107.5 (2)	C15—C14—H14	120.0
C3—C2—C1	127.9 (2)	C14—C15—C10	120.0 (4)
N1—C2—C1	124.1 (2)	C14—C15—H15	120.0
C2—C3—C4	110.2 (2)	C10—C15—H15	120.0
C2—C3—S2	125.4 (2)	C21—C16—C17	118.8 (3)
C4—C3—S2	124.3 (2)	C21—C16—S2	124.6 (2)
C5—C4—C9	119.6 (3)	C17—C16—S2	116.5 (2)
C5—C4—C3	133.4 (3)	C18—C17—C16	120.2 (3)
C9—C4—C3	106.9 (2)	C18—C17—H17	119.9
C6—C5—C4	119.2 (3)	C16—C17—H17	119.9
C6—C5—H5	120.4	C19—C18—C17	121.4 (3)
C4—C5—H5	120.4	C19—C18—H18	119.3
C5—C6—C7	120.9 (3)	C17—C18—H18	119.3
C5—C6—H6	119.6	C18—C19—C20	119.7 (3)
C7—C6—H6	119.6	C18—C19—H19	120.1
C6—C7—C8	121.5 (3)	C20—C19—H19	120.1
C6—C7—H7	119.2	C19—C20—C21	119.7 (3)
C8—C7—H7	119.2	C19—C20—H20	120.2
C7—C8—C9	117.7 (3)	C21—C20—H20	120.2
C7—C8—H8	121.2	C16—C21—C20	120.2 (3)
C9—C8—H8	121.2	C16—C21—H21	119.9
C8—C9—C4	121.0 (3)	C20—C21—H21	119.9
O2—S1—N1—C9	−179.1 (2)	C5—C4—C9—N1	−178.1 (3)
O1—S1—N1—C9	−50.1 (2)	C3—C4—C9—N1	1.8 (3)
C10—S1—N1—C9	64.7 (2)	C2—N1—C9—C8	178.1 (3)
O2—S1—N1—C2	36.7 (2)	S1—N1—C9—C8	28.8 (4)
O1—S1—N1—C2	165.7 (2)	C2—N1—C9—C4	−2.5 (3)
C10—S1—N1—C2	−79.5 (2)	S1—N1—C9—C4	−151.8 (2)
C9—N1—C2—C3	2.2 (3)	O2—S1—C10—C11	135.7 (3)
S1—N1—C2—C3	150.3 (2)	O1—S1—C10—C11	2.4 (3)
C9—N1—C2—C1	175.1 (2)	N1—S1—C10—C11	−110.5 (3)
S1—N1—C2—C1	−36.8 (3)	O2—S1—C10—C15	−47.8 (3)
C1^i—C1—C2—C3	102.7 (3)	O1—S1—C10—C15	178.9 (3)
C1^i—C1—C2—N1	−68.7 (4)	N1—S1—C10—C15	66.0 (3)
N1—C2—C3—C4	−1.2 (3)	C15—C10—C11—C12	2.8 (6)
C1—C2—C3—C4	−173.7 (2)	S1—C10—C11—C12	179.3 (3)
N1—C2—C3—S2	175.1 (2)	C10—C11—C12—C13	−3.2 (7)
C1—C2—C3—S2	2.5 (4)	C11—C12—C13—C14	1.0 (7)
C16—S2—C3—C2	119.5 (3)	C12—C13—C14—C15	1.6 (7)
C16—S2—C3—C4	−64.8 (3)	C13—C14—C15—C10	−1.9 (7)
C2—C3—C4—C5	179.5 (3)	C11—C10—C15—C14	−0.3 (6)
S2—C3—C4—C5	3.2 (5)	S1—C10—C15—C14	−176.8 (3)
C2—C3—C4—C9	−0.3 (3)	C3—S2—C16—C21	−23.4 (3)
S2—C3—C4—C9	−176.6 (2)	C3—S2—C16—C17	158.2 (2)
C9—C4—C5—C6	−0.7 (5)	C21—C16—C17—C18	0.4 (5)
C3—C4—C5—C6	179.5 (3)	S2—C16—C17—C18	178.9 (3)
C4—C5—C6—C7	0.0 (6)	C16—C17—C18—C19	0.7 (5)
C5—C6—C7—C8	0.0 (6)	C17—C18—C19—C20	−0.7 (6)
C6—C7—C8—C9	0.7 (5)	C18—C19—C20—C21	−0.4 (5)
C7—C8—C9—C4	−1.3 (4)	C17—C16—C21—C20	−1.5 (5)
C7—C8—C9—N1	178.0 (3)	S2—C16—C21—C20	−179.9 (2)
C5—C4—C9—C8	1.4 (4)	C19—C20—C21—C16	1.5 (5)
C3—C4—C9—C8	−178.8 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···S2	0.97	2.85	3.292 (3)	109
C1—H1B···O2	0.97	2.30	2.857 (3)	115
C8—H8···O1	0.93	2.41	2.985 (4)	120
C11—H11···O1	0.93	2.54	2.913 (4)	105