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The title compound, C42H30N2O4S4, crystallizes in the space group P\overline 1 with half a mol­ecule in the asymmetric unit and the other half generated by an inversion centre. The indole moiety is planar within \pm0.043 (1) Å. The dihedral angle between the indole system and the thio­phenyl ring is 83.4 (1)°. The S atom of the sulfonyl substituent has a distorted tetrahedral geometry. The molecular structure is stabilized by C—H...O and C—H...S interactions and the packing of the mol­ecules in the solid state is stabilized by C—H...O, C—H...π and π–π intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802023188/ci6193sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802023188/ci6193Isup2.hkl
Contains datablock I

CCDC reference: 192319

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1,2-Bis[1-phenylsulfonyl-3-(phenylthio)indol-2-yl]ethene top
Crystal data top
C42H30N2O4S4Z = 1
Mr = 754.92F(000) = 392
Triclinic, P1Dx = 1.427 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2920 (2) ÅCell parameters from 5090 reflections
b = 9.5524 (3) Åθ = 2.3–28.3°
c = 11.3921 (3) ŵ = 0.32 mm1
α = 67.379 (1)°T = 293 K
β = 72.821 (1)°Block, colourless
γ = 74.589 (1)°0.46 × 0.40 × 0.32 mm
V = 878.37 (4) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer
3499 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 28.3°, θmin = 2.3°
ω scansh = 1012
6040 measured reflectionsk = 1212
4138 independent reflectionsl = 1514
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0767P)2 + 0.0306P]
where P = (Fo2 + 2Fc2)/3
4138 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.19036 (4)0.77234 (4)0.14479 (4)0.04120 (13)
S20.79898 (4)0.53525 (5)0.08169 (4)0.04196 (13)
O10.14649 (13)0.75278 (14)0.04310 (12)0.0505 (3)
O20.11574 (15)0.90070 (15)0.18791 (15)0.0625 (4)
N10.37892 (14)0.78381 (13)0.09635 (12)0.0354 (3)
C10.49156 (15)0.65937 (15)0.06706 (13)0.0324 (3)
C20.62293 (16)0.65819 (16)0.09971 (14)0.0352 (3)
C40.44633 (18)0.85940 (16)0.14685 (13)0.0379 (3)
C30.59817 (18)0.78506 (17)0.14682 (13)0.0388 (3)
C50.6975 (2)0.8430 (2)0.18095 (17)0.0529 (4)
H50.79930.79630.17850.063*
C60.6384 (3)0.9727 (2)0.21869 (18)0.0619 (5)
H60.70151.01260.24310.074*
C70.4883 (3)1.0432 (2)0.22063 (18)0.0596 (5)
H70.45271.12900.24760.071*
C80.3882 (2)0.99143 (18)0.18400 (16)0.0499 (4)
H80.28761.04150.18400.060*
C90.18600 (17)0.60084 (19)0.27974 (15)0.0406 (3)
C100.2173 (2)0.5962 (2)0.39345 (17)0.0542 (4)
H100.23800.68310.39910.065*
C110.2170 (2)0.4601 (3)0.49803 (18)0.0622 (5)
H110.23820.45560.57440.075*
C120.1859 (2)0.3316 (3)0.4902 (2)0.0624 (5)
H120.18630.24070.56090.075*
C130.1541 (3)0.3376 (2)0.3769 (2)0.0639 (5)
H130.13240.25060.37210.077*
C140.1543 (2)0.4725 (2)0.27028 (18)0.0508 (4)
H140.13350.47650.19400.061*
C150.77201 (16)0.37086 (17)0.22466 (14)0.0364 (3)
C160.89272 (19)0.24669 (19)0.23659 (17)0.0454 (3)
H160.97910.24990.16930.055*
C170.8846 (2)0.1187 (2)0.34806 (18)0.0527 (4)
H170.96660.03740.35640.063*
C180.7542 (2)0.1112 (2)0.44768 (17)0.0547 (4)
H180.74890.02510.52270.066*
C190.6328 (2)0.2317 (2)0.43492 (18)0.0578 (5)
H190.54510.22610.50110.069*
C200.6403 (2)0.3622 (2)0.32364 (17)0.0499 (4)
H200.55780.44310.31550.060*
C210.46027 (16)0.56928 (16)0.00201 (14)0.0348 (3)
H210.37900.61090.04000.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0336 (2)0.0427 (2)0.0459 (2)0.00367 (15)0.00649 (15)0.02159 (17)
S20.02939 (19)0.0474 (2)0.0447 (2)0.00699 (14)0.00625 (14)0.01182 (16)
O10.0412 (6)0.0592 (7)0.0528 (7)0.0028 (5)0.0178 (5)0.0223 (6)
O20.0500 (7)0.0555 (8)0.0809 (10)0.0116 (6)0.0066 (6)0.0407 (7)
N10.0360 (6)0.0329 (6)0.0375 (6)0.0024 (5)0.0046 (5)0.0168 (5)
C10.0314 (6)0.0318 (6)0.0326 (6)0.0028 (5)0.0040 (5)0.0132 (5)
C20.0357 (7)0.0344 (7)0.0348 (7)0.0070 (5)0.0075 (5)0.0102 (5)
C40.0516 (8)0.0322 (7)0.0292 (6)0.0116 (6)0.0043 (6)0.0096 (5)
C30.0506 (8)0.0373 (7)0.0297 (6)0.0153 (6)0.0084 (6)0.0076 (5)
C50.0684 (11)0.0532 (10)0.0454 (9)0.0244 (8)0.0199 (8)0.0106 (7)
C60.0966 (16)0.0565 (10)0.0476 (9)0.0375 (11)0.0202 (10)0.0140 (8)
C70.0975 (16)0.0440 (9)0.0434 (9)0.0278 (10)0.0049 (9)0.0185 (7)
C80.0722 (11)0.0350 (8)0.0396 (8)0.0133 (7)0.0007 (7)0.0161 (6)
C90.0319 (7)0.0510 (8)0.0381 (7)0.0063 (6)0.0006 (5)0.0205 (6)
C100.0600 (11)0.0643 (11)0.0454 (9)0.0175 (9)0.0073 (8)0.0245 (8)
C110.0658 (12)0.0817 (14)0.0407 (9)0.0200 (10)0.0100 (8)0.0184 (9)
C120.0625 (12)0.0658 (12)0.0519 (10)0.0184 (10)0.0113 (8)0.0081 (9)
C130.0759 (14)0.0564 (11)0.0623 (12)0.0226 (10)0.0162 (10)0.0147 (9)
C140.0543 (10)0.0553 (10)0.0467 (9)0.0143 (8)0.0095 (7)0.0190 (8)
C150.0357 (7)0.0411 (7)0.0374 (7)0.0047 (6)0.0124 (6)0.0162 (6)
C160.0402 (8)0.0494 (9)0.0488 (8)0.0011 (6)0.0120 (6)0.0227 (7)
C170.0591 (10)0.0442 (9)0.0572 (10)0.0076 (7)0.0216 (8)0.0236 (8)
C180.0764 (13)0.0424 (9)0.0427 (9)0.0053 (8)0.0158 (8)0.0123 (7)
C190.0615 (11)0.0551 (10)0.0430 (9)0.0058 (8)0.0015 (8)0.0118 (8)
C200.0444 (9)0.0490 (9)0.0451 (9)0.0018 (7)0.0048 (7)0.0139 (7)
C210.0300 (6)0.0381 (7)0.0395 (7)0.0037 (5)0.0069 (5)0.0182 (6)
Geometric parameters (Å, º) top
S1—O11.4244 (12)C10—C111.385 (3)
S1—O21.4268 (12)C10—H100.93
S1—N11.6943 (13)C11—C121.373 (3)
S1—C91.7635 (17)C11—H110.93
S2—C21.7502 (15)C12—C131.384 (3)
S2—C151.7839 (15)C12—H120.93
N1—C41.4204 (18)C13—C141.390 (3)
N1—C11.4343 (16)C13—H130.93
C1—C21.3734 (18)C14—H140.93
C1—C211.4578 (18)C15—C201.394 (2)
C2—C31.4453 (19)C15—C161.394 (2)
C4—C31.401 (2)C16—C171.382 (2)
C4—C81.405 (2)C16—H160.93
C3—C51.399 (2)C17—C181.390 (3)
C5—C61.390 (3)C17—H170.93
C5—H50.93C18—C191.377 (3)
C6—C71.376 (3)C18—H180.93
C6—H60.93C19—C201.394 (2)
C7—C81.385 (3)C19—H190.93
C7—H70.93C20—H200.93
C8—H80.93C21—C21i1.344 (3)
C9—C141.383 (2)C21—H210.93
C9—C101.391 (2)
O1—S1—O2120.04 (8)C11—C10—C9118.97 (17)
O1—S1—N1107.77 (7)C11—C10—H10120.5
O2—S1—N1106.17 (7)C9—C10—H10120.5
O1—S1—C9109.31 (7)C12—C11—C10120.69 (18)
O2—S1—C9109.55 (8)C12—C11—H11119.7
N1—S1—C9102.53 (7)C10—C11—H11119.7
C2—S2—C15102.69 (7)C11—C12—C13119.93 (19)
C4—N1—C1108.05 (12)C11—C12—H12120.0
C4—N1—S1122.14 (10)C13—C12—H12120.0
C1—N1—S1121.22 (10)C12—C13—C14120.55 (18)
C2—C1—N1107.87 (12)C12—C13—H13119.7
C2—C1—C21131.17 (12)C14—C13—H13119.7
N1—C1—C21120.69 (12)C9—C14—C13118.80 (16)
C1—C2—C3108.75 (12)C9—C14—H14120.6
C1—C2—S2128.20 (11)C13—C14—H14120.6
C3—C2—S2122.95 (11)C20—C15—C16119.44 (15)
C3—C4—C8121.30 (15)C20—C15—S2123.82 (12)
C3—C4—N1107.73 (12)C16—C15—S2116.73 (12)
C8—C4—N1130.82 (15)C17—C16—C15120.28 (16)
C5—C3—C4120.60 (15)C17—C16—H16119.9
C5—C3—C2131.72 (16)C15—C16—H16119.9
C4—C3—C2107.55 (13)C16—C17—C18120.22 (16)
C6—C5—C3117.59 (19)C16—C17—H17119.9
C6—C5—H5121.2C18—C17—H17119.9
C3—C5—H5121.2C19—C18—C17119.75 (17)
C7—C6—C5121.33 (17)C19—C18—H18120.1
C7—C6—H6119.3C17—C18—H18120.1
C5—C6—H6119.3C18—C19—C20120.60 (17)
C6—C7—C8122.55 (16)C18—C19—H19119.7
C6—C7—H7118.7C20—C19—H19119.7
C8—C7—H7118.7C15—C20—C19119.66 (16)
C7—C8—C4116.59 (18)C15—C20—H20120.2
C7—C8—H8121.7C19—C20—H20120.2
C4—C8—H8121.7C21i—C21—C1125.09 (17)
C14—C9—C10121.06 (17)C21i—C21—H21117.5
C14—C9—S1119.64 (13)C1—C21—H21117.5
C10—C9—S1119.29 (13)
O1—S1—N1—C4155.46 (11)C5—C6—C7—C80.8 (3)
O2—S1—N1—C425.65 (14)C6—C7—C8—C41.4 (3)
C9—S1—N1—C489.26 (12)C3—C4—C8—C70.2 (2)
O1—S1—N1—C160.57 (12)N1—C4—C8—C7175.12 (15)
O2—S1—N1—C1169.62 (11)O1—S1—C9—C144.43 (16)
C9—S1—N1—C154.71 (12)O2—S1—C9—C14137.84 (14)
C4—N1—C1—C20.52 (15)N1—S1—C9—C14109.72 (14)
S1—N1—C1—C2147.88 (10)O1—S1—C9—C10176.70 (13)
C4—N1—C1—C21174.15 (12)O2—S1—C9—C1043.28 (15)
S1—N1—C1—C2137.45 (17)N1—S1—C9—C1069.15 (14)
N1—C1—C2—C31.76 (16)C14—C9—C10—C110.3 (3)
C21—C1—C2—C3172.15 (14)S1—C9—C10—C11178.55 (14)
N1—C1—C2—S2178.28 (10)C9—C10—C11—C120.2 (3)
C21—C1—C2—S24.4 (2)C10—C11—C12—C130.1 (3)
C15—S2—C2—C184.02 (14)C11—C12—C13—C140.4 (3)
C15—S2—C2—C399.91 (13)C10—C9—C14—C130.0 (3)
C1—N1—C4—C30.95 (15)S1—C9—C14—C13178.85 (14)
S1—N1—C4—C3149.01 (10)C12—C13—C14—C90.4 (3)
C1—N1—C4—C8176.41 (15)C2—S2—C15—C203.92 (15)
S1—N1—C4—C835.5 (2)C2—S2—C15—C16177.33 (11)
C8—C4—C3—C51.6 (2)C20—C15—C16—C172.7 (2)
N1—C4—C3—C5174.39 (14)S2—C15—C16—C17176.08 (12)
C8—C4—C3—C2177.97 (13)C15—C16—C17—C181.7 (2)
N1—C4—C3—C21.99 (15)C16—C17—C18—C190.1 (3)
C1—C2—C3—C5173.47 (16)C17—C18—C19—C200.8 (3)
S2—C2—C3—C53.3 (2)C16—C15—C20—C192.0 (3)
C1—C2—C3—C42.36 (16)S2—C15—C20—C19176.74 (13)
S2—C2—C3—C4179.10 (10)C18—C19—C20—C150.2 (3)
C4—C3—C5—C62.1 (2)C2—C1—C21—C21i23.6 (3)
C2—C3—C5—C6177.50 (16)N1—C1—C21—C21i163.16 (18)
C3—C5—C6—C71.0 (3)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O20.932.332.869 (2)117
C14—H14···O10.932.552.924 (2)105
C21—H21···O10.932.372.984 (2)123
C21—H21···S2i0.932.673.328 (2)129
C17—H17···O2ii0.932.593.242 (2)128
C6—H6···Cg(B)iii0.932.993.842 (2)153
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y1, z; (iii) x, y+1, z.
 

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