3-Ethenyl-1-(4-methyl-phenyl-sulfon-yl)-1H-indole.

Two independent but very similar mol-ecules comprise the asymmetric unit of the title compound, C(17)H(15)NO(2)S. The mol-ecules have L-shapes with the dihedral angles between the fused-ring system (r.m.s. deviations = 0.036 and 0.019 Å, respectively) and the benzene ring being almost the same, i.e. 82.98 (12) and 84.46 (13)°, respectively. The terminal ethenyl group is almost coplanar with the ring to which it is connected [C-C-C-C torsion angles = -173.7 (4) and -171.7 (4)°, respectively]. Supra-molecular arrays parallel to (-124) stabilized by C-H⋯O and C-H⋯π inter-actions feature in the crystal packing.

Related literature

For background to the biological activity of indole­amine 2,3-di­oxy­genase and inhibitors, see: Rohrig et al. (2010 ▶); Munn & Mellor (2007 ▶); Muller et al. (2005 ▶). For related structures, see: Seshadri et al. (2002 ▶); Senthil Kumar et al. (2006 ▶); Chakkaravarthi et al. (2008 ▶).

Experimental

Crystal data

C17H15NO2S

M = 297.37

Triclinic,

a = 9.8809 (4) Å

b = 10.0167 (3) Å

c = 15.5280 (5) Å

α = 83.687 (3)°

β = 77.864 (3)°

γ = 88.769 (3)°

V = 1493.41 (9) Å3

Z = 4

Cu Kα radiation

μ = 1.95 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova (Dual, Cu at zero) diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.548, T max = 0.641

11566 measured reflections

6103 independent reflections

5505 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.185

S = 1.02

6103 reflections

381 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), QMol (Gans & Shalloway, 2001 ▶), DIAMOND (Brandenburg, 2006 ▶) and MarvinSketch (ChemAxon, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021526/hg5227sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021526/hg5227Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021526/hg5227Isup3.cml

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

C17H15NO2S	Z = 4
Mr = 297.37	F(000) = 624
Triclinic, P1	Dx = 1.323 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.8809 (4) Å	Cell parameters from 5330 reflections
b = 10.0167 (3) Å	θ = 2.9–75.8°
c = 15.5280 (5) Å	µ = 1.95 mm−1
α = 83.687 (3)°	T = 100 K
β = 77.864 (3)°	Prism, colourless
γ = 88.769 (3)°	0.35 × 0.30 × 0.25 mm
V = 1493.41 (9) Å3

Agilent SuperNova (Dual, Cu at zero) diffractometer with an Atlas detector	6103 independent reflections
Radiation source: fine-focus sealed tube	5505 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 10.4041 pixels mm-1	θmax = 76.0°, θmin = 2.9°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→11
Tmin = 0.548, Tmax = 0.641	l = −19→17
11566 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0942P)2 + 2.0717P] where P = (Fo2 + 2Fc2)/3
6103 reflections	(Δ/σ)max < 0.001
381 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
S1	0.71402 (8)	0.06134 (7)	0.57164 (4)	0.0379 (2)
S2	0.89812 (7)	0.71152 (6)	0.08641 (4)	0.03595 (19)
O1	0.8589 (2)	0.0488 (2)	0.56504 (14)	0.0471 (5)
O2	0.6524 (3)	0.0203 (2)	0.50369 (14)	0.0542 (6)
O3	0.9112 (2)	0.8520 (2)	0.08884 (15)	0.0480 (5)
O4	0.9752 (2)	0.6483 (2)	0.01369 (14)	0.0483 (5)
N1	0.6393 (3)	−0.0306 (2)	0.66474 (16)	0.0382 (5)
N2	0.9472 (3)	0.6333 (3)	0.17477 (16)	0.0404 (5)
C1	0.6788 (4)	−0.0325 (3)	0.74573 (19)	0.0449 (7)
C2	0.7995 (4)	0.0015 (3)	0.7654 (2)	0.0493 (7)
H2	0.8760	0.0333	0.7202	0.059*
C3	0.8076 (4)	−0.0119 (4)	0.8550 (2)	0.0553 (8)
H3	0.8898	0.0140	0.8715	0.066*
C4	0.6984 (4)	−0.0617 (3)	0.9187 (2)	0.0544 (9)
H4	0.7090	−0.0756	0.9784	0.065*
C5	0.5724 (4)	−0.0930 (3)	0.8997 (2)	0.0559 (9)
H5	0.4975	−0.1239	0.9463	0.067*
C6	0.5557 (4)	−0.0792 (3)	0.81181 (19)	0.0420 (7)
C7	0.4485 (4)	−0.0954 (3)	0.7646 (2)	0.0482 (7)
C8	0.4978 (4)	−0.0643 (3)	0.6777 (2)	0.0464 (7)
H8	0.4464	−0.0648	0.6325	0.056*
C9	0.3022 (4)	−0.1397 (3)	0.7985 (3)	0.0592 (9)
H9	0.2490	−0.1537	0.7559	0.071*
C10	0.2413 (5)	−0.1609 (4)	0.8818 (3)	0.0692 (11)
H10A	0.2909	−0.1481	0.9265	0.083*
H10B	0.1474	−0.1891	0.8979	0.083*
C11	0.6616 (3)	0.2251 (3)	0.59101 (17)	0.0352 (6)
C12	0.7527 (3)	0.3103 (3)	0.61593 (18)	0.0406 (6)
H12	0.8434	0.2813	0.6204	0.049*
C13	0.7080 (4)	0.4379 (3)	0.6340 (2)	0.0471 (7)
H13	0.7696	0.4979	0.6499	0.057*
C14	0.5751 (4)	0.4798 (3)	0.6294 (2)	0.0472 (7)
C15	0.4850 (3)	0.3920 (3)	0.6042 (2)	0.0466 (7)
H15	0.3938	0.4204	0.6006	0.056*
C16	0.5281 (3)	0.2648 (3)	0.58467 (19)	0.0410 (6)
H16	0.4676	0.2054	0.5672	0.049*
C17	0.5264 (5)	0.6181 (3)	0.6508 (3)	0.0652 (11)
H17A	0.5739	0.6469	0.6951	0.098*
H17B	0.4263	0.6161	0.6745	0.098*
H17C	0.5472	0.6811	0.5969	0.098*
C18	0.9102 (3)	0.6694 (3)	0.2611 (2)	0.0421 (6)
C19	0.8755 (3)	0.7930 (3)	0.2880 (2)	0.0485 (7)
H19	0.8698	0.8696	0.2470	0.058*
C20	0.8481 (4)	0.8009 (4)	0.3812 (2)	0.0560 (9)
H20	0.8223	0.8846	0.4033	0.067*
C21	0.8583 (4)	0.6908 (4)	0.4390 (2)	0.0584 (9)
H21	0.8402	0.6998	0.5007	0.070*
C22	0.8945 (4)	0.5654 (4)	0.4106 (2)	0.0507 (8)
H22	0.9018	0.4896	0.4519	0.061*
C23	0.9197 (3)	0.5538 (3)	0.32029 (18)	0.0365 (6)
C24	0.9604 (3)	0.4422 (3)	0.2660 (2)	0.0427 (7)
C25	0.9723 (3)	0.4917 (3)	0.18085 (19)	0.0414 (6)
H25	0.9943	0.4404	0.1318	0.050*
C26	0.9893 (3)	0.3026 (3)	0.2919 (2)	0.0493 (7)
H26	1.0293	0.2505	0.2455	0.059*
C27	0.9658 (4)	0.2395 (4)	0.3737 (2)	0.0627 (10)
H27A	0.9260	0.2868	0.4227	0.075*
H27B	0.9890	0.1473	0.3831	0.075*
C28	0.7235 (3)	0.6688 (3)	0.10340 (16)	0.0350 (6)
C29	0.6230 (3)	0.7598 (3)	0.13615 (18)	0.0406 (6)
H29	0.6483	0.8447	0.1498	0.049*
C30	0.4852 (3)	0.7244 (4)	0.14844 (19)	0.0475 (7)
H30	0.4156	0.7863	0.1703	0.057*
C31	0.4465 (4)	0.5999 (4)	0.1294 (2)	0.0528 (8)
C32	0.5503 (4)	0.5089 (4)	0.0993 (2)	0.0510 (8)
H32	0.5253	0.4224	0.0882	0.061*
C33	0.6889 (3)	0.5426 (3)	0.08540 (19)	0.0428 (7)
H33	0.7589	0.4807	0.0640	0.051*
C34	0.2970 (4)	0.5637 (6)	0.1404 (3)	0.0743 (12)
H34A	0.2841	0.4677	0.1603	0.111*
H34B	0.2686	0.5838	0.0836	0.111*
H34C	0.2404	0.6160	0.1845	0.111*

	U11	U22	U33	U12	U13	U23
S1	0.0481 (4)	0.0398 (4)	0.0250 (3)	0.0088 (3)	−0.0040 (3)	−0.0082 (2)
S2	0.0461 (4)	0.0315 (3)	0.0261 (3)	0.0029 (3)	0.0007 (3)	−0.0015 (2)
O1	0.0473 (12)	0.0503 (12)	0.0362 (11)	0.0102 (9)	0.0053 (9)	−0.0015 (9)
O2	0.0745 (16)	0.0575 (14)	0.0364 (11)	0.0124 (12)	−0.0174 (11)	−0.0212 (10)
O3	0.0620 (14)	0.0317 (10)	0.0446 (12)	−0.0025 (9)	0.0007 (10)	−0.0017 (8)
O4	0.0577 (13)	0.0453 (12)	0.0345 (11)	0.0038 (10)	0.0089 (9)	−0.0086 (9)
N1	0.0436 (13)	0.0332 (11)	0.0343 (12)	0.0008 (9)	0.0005 (10)	−0.0058 (9)
N2	0.0424 (13)	0.0452 (13)	0.0315 (12)	0.0022 (10)	−0.0054 (10)	−0.0004 (10)
C1	0.072 (2)	0.0307 (13)	0.0294 (14)	0.0035 (13)	−0.0069 (13)	−0.0019 (11)
C2	0.0564 (19)	0.0441 (16)	0.0438 (17)	0.0082 (14)	−0.0053 (14)	−0.0005 (13)
C3	0.067 (2)	0.0507 (19)	0.0508 (19)	0.0103 (16)	−0.0198 (17)	−0.0053 (15)
C4	0.081 (3)	0.0498 (18)	0.0329 (15)	0.0047 (17)	−0.0178 (16)	0.0056 (13)
C5	0.080 (3)	0.0447 (17)	0.0365 (16)	0.0042 (16)	−0.0017 (16)	0.0019 (13)
C6	0.0633 (19)	0.0284 (13)	0.0318 (14)	0.0089 (12)	−0.0043 (13)	−0.0045 (10)
C7	0.063 (2)	0.0314 (14)	0.0487 (17)	0.0036 (13)	−0.0063 (15)	−0.0068 (12)
C8	0.0548 (18)	0.0334 (14)	0.0509 (18)	0.0014 (13)	−0.0091 (14)	−0.0075 (12)
C9	0.055 (2)	0.0377 (16)	0.077 (3)	−0.0096 (14)	0.0078 (18)	−0.0125 (16)
C10	0.078 (3)	0.054 (2)	0.071 (3)	−0.0040 (19)	−0.003 (2)	−0.0106 (19)
C11	0.0450 (15)	0.0355 (13)	0.0231 (12)	0.0059 (11)	−0.0041 (10)	−0.0011 (10)
C12	0.0457 (16)	0.0435 (15)	0.0306 (13)	0.0015 (12)	−0.0054 (11)	−0.0006 (11)
C13	0.064 (2)	0.0373 (15)	0.0389 (15)	−0.0025 (14)	−0.0102 (14)	−0.0016 (12)
C14	0.068 (2)	0.0361 (15)	0.0346 (15)	0.0087 (14)	−0.0058 (14)	−0.0015 (11)
C15	0.0489 (17)	0.0452 (16)	0.0424 (16)	0.0120 (13)	−0.0062 (13)	0.0014 (13)
C16	0.0464 (16)	0.0416 (15)	0.0338 (14)	0.0045 (12)	−0.0078 (12)	−0.0009 (11)
C17	0.097 (3)	0.0376 (17)	0.058 (2)	0.0162 (18)	−0.011 (2)	−0.0059 (15)
C18	0.0384 (15)	0.0517 (17)	0.0356 (14)	−0.0015 (12)	−0.0042 (11)	−0.0082 (12)
C19	0.0467 (17)	0.0479 (17)	0.0505 (18)	−0.0021 (13)	−0.0081 (14)	−0.0068 (14)
C20	0.0501 (19)	0.059 (2)	0.059 (2)	−0.0021 (15)	−0.0004 (15)	−0.0293 (17)
C21	0.053 (2)	0.087 (3)	0.0372 (17)	−0.0017 (18)	−0.0054 (14)	−0.0227 (17)
C22	0.0513 (18)	0.064 (2)	0.0368 (16)	−0.0004 (15)	−0.0078 (13)	−0.0070 (14)
C23	0.0302 (13)	0.0460 (15)	0.0336 (13)	0.0001 (11)	−0.0072 (10)	−0.0049 (11)
C24	0.0399 (15)	0.0474 (17)	0.0406 (15)	0.0024 (12)	−0.0079 (12)	−0.0049 (12)
C25	0.0382 (15)	0.0496 (17)	0.0374 (15)	0.0048 (12)	−0.0064 (12)	−0.0136 (12)
C26	0.0469 (17)	0.0443 (17)	0.0538 (18)	0.0081 (13)	−0.0037 (14)	−0.0069 (14)
C27	0.075 (3)	0.061 (2)	0.0469 (19)	0.0113 (19)	−0.0055 (17)	0.0011 (16)
C28	0.0449 (15)	0.0355 (13)	0.0229 (11)	0.0054 (11)	−0.0057 (10)	0.0003 (10)
C29	0.0536 (17)	0.0387 (14)	0.0263 (13)	0.0097 (12)	−0.0037 (11)	−0.0006 (10)
C30	0.0484 (17)	0.062 (2)	0.0298 (14)	0.0139 (15)	−0.0043 (12)	−0.0055 (13)
C31	0.0482 (18)	0.079 (2)	0.0324 (15)	0.0026 (16)	−0.0108 (13)	−0.0078 (15)
C32	0.0564 (19)	0.0563 (19)	0.0450 (17)	−0.0009 (15)	−0.0182 (15)	−0.0112 (14)
C33	0.0543 (18)	0.0417 (15)	0.0350 (14)	0.0074 (13)	−0.0134 (12)	−0.0079 (12)
C34	0.050 (2)	0.121 (4)	0.057 (2)	−0.003 (2)	−0.0131 (17)	−0.028 (2)

S1—O1	1.418 (2)	C15—C16	1.381 (4)
S1—O2	1.424 (2)	C15—H15	0.9500
S1—N1	1.664 (2)	C16—H16	0.9500
S1—C11	1.748 (3)	C17—H17A	0.9800
S2—O3	1.421 (2)	C17—H17B	0.9800
S2—O4	1.425 (2)	C17—H17C	0.9800
S2—N2	1.661 (2)	C18—C19	1.364 (5)
S2—C28	1.745 (3)	C18—C23	1.412 (4)
N1—C1	1.391 (4)	C19—C20	1.426 (5)
N1—C8	1.413 (4)	C19—H19	0.9500
N2—C18	1.398 (4)	C20—C21	1.360 (6)
N2—C25	1.431 (4)	C20—H20	0.9500
C1—C2	1.351 (5)	C21—C22	1.392 (5)
C1—C6	1.464 (4)	C21—H21	0.9500
C2—C3	1.403 (5)	C22—C23	1.389 (4)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.363 (5)	C23—C24	1.473 (4)
C3—H3	0.9500	C24—C25	1.341 (4)
C4—C5	1.388 (6)	C24—C26	1.451 (4)
C4—H4	0.9500	C25—H25	0.9500
C5—C6	1.401 (4)	C26—C27	1.331 (5)
C5—H5	0.9500	C26—H26	0.9500
C6—C7	1.431 (5)	C27—H27A	0.9500
C7—C8	1.339 (5)	C27—H27B	0.9500
C7—C9	1.490 (5)	C28—C29	1.388 (4)
C8—H8	0.9500	C28—C33	1.390 (4)
C9—C10	1.304 (6)	C29—C30	1.383 (5)
C9—H9	0.9500	C29—H29	0.9500
C10—H10A	0.9500	C30—C31	1.392 (5)
C10—H10B	0.9500	C30—H30	0.9500
C11—C16	1.390 (4)	C31—C32	1.398 (5)
C11—C12	1.392 (4)	C31—C34	1.499 (5)
C12—C13	1.382 (4)	C32—C33	1.384 (5)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.384 (5)	C33—H33	0.9500
C13—H13	0.9500	C34—H34A	0.9800
C14—C15	1.406 (5)	C34—H34B	0.9800
C14—C17	1.505 (4)	C34—H34C	0.9800
O1—S1—O2	119.94 (14)	C15—C16—C11	118.7 (3)
O1—S1—N1	106.60 (13)	C15—C16—H16	120.6
O2—S1—N1	106.14 (14)	C11—C16—H16	120.6
O1—S1—C11	110.00 (14)	C14—C17—H17A	109.5
O2—S1—C11	109.24 (14)	C14—C17—H17B	109.5
N1—S1—C11	103.58 (12)	H17A—C17—H17B	109.5
O3—S2—O4	120.11 (13)	C14—C17—H17C	109.5
O3—S2—N2	107.90 (14)	H17A—C17—H17C	109.5
O4—S2—N2	104.62 (13)	H17B—C17—H17C	109.5
O3—S2—C28	109.69 (14)	C19—C18—N2	128.6 (3)
O4—S2—C28	109.70 (14)	C19—C18—C23	123.3 (3)
N2—S2—C28	103.42 (12)	N2—C18—C23	108.0 (3)
C1—N1—C8	110.5 (3)	C18—C19—C20	116.2 (3)
C1—N1—S1	125.2 (2)	C18—C19—H19	121.9
C8—N1—S1	118.9 (2)	C20—C19—H19	121.9
C18—N2—C25	107.6 (2)	C21—C20—C19	121.2 (3)
C18—N2—S2	125.8 (2)	C21—C20—H20	119.4
C25—N2—S2	120.4 (2)	C19—C20—H20	119.4
C2—C1—N1	131.0 (3)	C20—C21—C22	121.9 (3)
C2—C1—C6	124.3 (3)	C20—C21—H21	119.0
N1—C1—C6	104.7 (3)	C22—C21—H21	119.0
C1—C2—C3	117.4 (3)	C23—C22—C21	118.4 (3)
C1—C2—H2	121.3	C23—C22—H22	120.8
C3—C2—H2	121.3	C21—C22—H22	120.8
C4—C3—C2	120.4 (4)	C22—C23—C18	119.0 (3)
C4—C3—H3	119.8	C22—C23—C24	134.2 (3)
C2—C3—H3	119.8	C18—C23—C24	106.8 (2)
C3—C4—C5	122.6 (3)	C25—C24—C26	122.2 (3)
C3—C4—H4	118.7	C25—C24—C23	107.5 (3)
C5—C4—H4	118.7	C26—C24—C23	130.3 (3)
C4—C5—C6	120.0 (3)	C24—C25—N2	110.0 (3)
C4—C5—H5	120.0	C24—C25—H25	125.0
C6—C5—H5	120.0	N2—C25—H25	125.0
C5—C6—C7	138.2 (3)	C27—C26—C24	127.1 (3)
C5—C6—C1	115.0 (3)	C27—C26—H26	116.4
C7—C6—C1	106.8 (3)	C24—C26—H26	116.4
C8—C7—C6	109.5 (3)	C26—C27—H27A	120.0
C8—C7—C9	120.7 (3)	C26—C27—H27B	120.0
C6—C7—C9	129.8 (3)	H27A—C27—H27B	120.0
C7—C8—N1	108.4 (3)	C29—C28—C33	121.6 (3)
C7—C8—H8	125.8	C29—C28—S2	119.6 (2)
N1—C8—H8	125.8	C33—C28—S2	118.8 (2)
C10—C9—C7	125.3 (4)	C30—C29—C28	118.7 (3)
C10—C9—H9	117.4	C30—C29—H29	120.7
C7—C9—H9	117.4	C28—C29—H29	120.7
C9—C10—H10A	120.0	C29—C30—C31	121.3 (3)
C9—C10—H10B	120.0	C29—C30—H30	119.4
H10A—C10—H10B	120.0	C31—C30—H30	119.4
C16—C11—C12	121.9 (3)	C30—C31—C32	118.5 (3)
C16—C11—S1	118.9 (2)	C30—C31—C34	121.0 (3)
C12—C11—S1	119.1 (2)	C32—C31—C34	120.4 (4)
C13—C12—C11	118.4 (3)	C33—C32—C31	121.2 (3)
C13—C12—H12	120.8	C33—C32—H32	119.4
C11—C12—H12	120.8	C31—C32—H32	119.4
C12—C13—C14	121.1 (3)	C32—C33—C28	118.6 (3)
C12—C13—H13	119.4	C32—C33—H33	120.7
C14—C13—H13	119.4	C28—C33—H33	120.7
C13—C14—C15	119.4 (3)	C31—C34—H34A	109.5
C13—C14—C17	120.8 (3)	C31—C34—H34B	109.5
C15—C14—C17	119.8 (3)	H34A—C34—H34B	109.5
C16—C15—C14	120.4 (3)	C31—C34—H34C	109.5
C16—C15—H15	119.8	H34A—C34—H34C	109.5
C14—C15—H15	119.8	H34B—C34—H34C	109.5
O1—S1—N1—C1	44.2 (3)	C12—C13—C14—C17	178.9 (3)
O2—S1—N1—C1	173.1 (2)	C13—C14—C15—C16	0.4 (5)
C11—S1—N1—C1	−71.9 (3)	C17—C14—C15—C16	−179.8 (3)
O1—S1—N1—C8	−164.4 (2)	C14—C15—C16—C11	0.4 (4)
O2—S1—N1—C8	−35.4 (2)	C12—C11—C16—C15	−0.4 (4)
C11—S1—N1—C8	79.6 (2)	S1—C11—C16—C15	176.9 (2)
O3—S2—N2—C18	44.1 (3)	C25—N2—C18—C19	−179.2 (3)
O4—S2—N2—C18	173.1 (2)	S2—N2—C18—C19	−27.2 (5)
C28—S2—N2—C18	−72.1 (3)	C25—N2—C18—C23	3.3 (3)
O3—S2—N2—C25	−167.1 (2)	S2—N2—C18—C23	155.4 (2)
O4—S2—N2—C25	−38.1 (3)	N2—C18—C19—C20	−177.3 (3)
C28—S2—N2—C25	76.7 (2)	C23—C18—C19—C20	−0.1 (5)
C8—N1—C1—C2	−174.9 (3)	C18—C19—C20—C21	0.8 (5)
S1—N1—C1—C2	−21.4 (5)	C19—C20—C21—C22	−0.6 (6)
C8—N1—C1—C6	3.9 (3)	C20—C21—C22—C23	−0.4 (5)
S1—N1—C1—C6	157.4 (2)	C21—C22—C23—C18	1.1 (5)
N1—C1—C2—C3	−179.9 (3)	C21—C22—C23—C24	179.4 (3)
C6—C1—C2—C3	1.5 (5)	C19—C18—C23—C22	−0.8 (5)
C1—C2—C3—C4	2.1 (5)	N2—C18—C23—C22	176.8 (3)
C2—C3—C4—C5	−4.3 (5)	C19—C18—C23—C24	−179.5 (3)
C3—C4—C5—C6	2.8 (5)	N2—C18—C23—C24	−1.9 (3)
C4—C5—C6—C7	−177.8 (3)	C22—C23—C24—C25	−178.7 (3)
C4—C5—C6—C1	0.7 (4)	C18—C23—C24—C25	−0.3 (3)
C2—C1—C6—C5	−2.9 (4)	C22—C23—C24—C26	−0.7 (6)
N1—C1—C6—C5	178.2 (3)	C18—C23—C24—C26	177.7 (3)
C2—C1—C6—C7	176.1 (3)	C26—C24—C25—N2	−175.9 (3)
N1—C1—C6—C7	−2.8 (3)	C23—C24—C25—N2	2.4 (3)
C5—C6—C7—C8	179.3 (4)	C18—N2—C25—C24	−3.6 (3)
C1—C6—C7—C8	0.7 (3)	S2—N2—C25—C24	−157.5 (2)
C5—C6—C7—C9	−1.0 (6)	C25—C24—C26—C27	−171.7 (4)
C1—C6—C7—C9	−179.6 (3)	C23—C24—C26—C27	10.5 (6)
C6—C7—C8—N1	1.7 (3)	O3—S2—C28—C29	−14.6 (3)
C9—C7—C8—N1	−178.0 (3)	O4—S2—C28—C29	−148.5 (2)
C1—N1—C8—C7	−3.7 (3)	N2—S2—C28—C29	100.3 (2)
S1—N1—C8—C7	−159.0 (2)	O3—S2—C28—C33	166.8 (2)
C8—C7—C9—C10	−173.7 (4)	O4—S2—C28—C33	32.8 (3)
C6—C7—C9—C10	6.6 (6)	N2—S2—C28—C33	−78.4 (2)
O1—S1—C11—C16	169.2 (2)	C33—C28—C29—C30	−1.9 (4)
O2—S1—C11—C16	35.6 (3)	S2—C28—C29—C30	179.5 (2)
N1—S1—C11—C16	−77.2 (2)	C28—C29—C30—C31	0.6 (4)
O1—S1—C11—C12	−13.5 (3)	C29—C30—C31—C32	1.5 (5)
O2—S1—C11—C12	−147.1 (2)	C29—C30—C31—C34	−178.2 (3)
N1—S1—C11—C12	100.1 (2)	C30—C31—C32—C33	−2.3 (5)
C16—C11—C12—C13	−0.5 (4)	C34—C31—C32—C33	177.4 (3)
S1—C11—C12—C13	−177.8 (2)	C31—C32—C33—C28	1.0 (5)
C11—C12—C13—C14	1.3 (4)	C29—C28—C33—C32	1.1 (4)
C12—C13—C14—C15	−1.3 (5)	S2—C28—C33—C32	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.95	2.50	3.433 (4)	166
C20—H20···O2ii	0.95	2.52	3.373 (5)	149
C25—H25···O4iii	0.95	2.48	3.406 (4)	166
C30—H30···Cg1iv	0.95	2.77	3.617 (4)	149
C34—H34C···Cg2v	0.98	2.95	3.525 (4)	119
C12—H12···Cg3v	0.95	2.87	3.739 (3)	153
C15—H15···Cg3v	0.95	2.86	3.638 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, N2–C25 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.95	2.50	3.433 (4)	166
C20—H20⋯O2ii	0.95	2.52	3.373 (5)	149
C25—H25⋯O4iii	0.95	2.48	3.406 (4)	166
C30—H30⋯Cg1iv	0.95	2.77	3.617 (4)	149
C34—H34C⋯Cg2v	0.98	2.95	3.525 (4)	119
C12—H12⋯Cg3v	0.95	2.87	3.739 (3)	153
C15—H15⋯Cg3v	0.95	2.86	3.638 (3)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .