In the title compound, C
42H
32N
2O
4S
4, 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.
Supporting information
CCDC reference: 180784
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Needle, colourless |
Z = 2 | 0.46 × 0.16 × 0.12 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0499P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0046 (8) |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C1i | 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—C1i | 112.9 (3) | C11—C12—H12 | 119.8 |
C2—C1—H1A | 109.0 | C14—C13—C12 | 120.7 (4) |
C1i—C1—H1A | 109.0 | C14—C13—H13 | 119.7 |
C2—C1—H1B | 109.0 | C12—C13—H13 | 119.7 |
C1i—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) |
C1i—C1—C2—C3 | 102.7 (3) | O1—S1—C10—C15 | 178.9 (3) |
C1i—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) top
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 |