Crystal structure of 2-[2-phenyl-1-(phenyl-sulfon-yl)eth-yl]-1-phenyl-sulfonyl-1H-indole.

In the title compound, C28H23NO4S2, the indole ring system (r.m.s. deviation = 0.007 Å) subtends dihedral angles of 78.69 (13) and 38.97 (13)° with the planes of the N- and C-bonded sulfonyl-benzene rings, respectively, and these two benzene rings are inclined to each other at an angle of 65.45 (16)°. The methyl-ene-linked phenyl ring is twisted at an angle of 81.80 (13)° from the indole ring. The mol-ecular structure features two short intra-molecular C-H⋯O contacts, which both generate S(6) rings. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, generating a three-dimensional network.

Related literature

For the biological activity of indole derivatives, see: Chen et al. (2015 ▸); Ferro et al. (2015 ▸); Parrino et al. (2015 ▸); Ma et al. (2015 ▸). For a related structure, see: Umadevi et al. (2015 ▸).

Experimental

Crystal data

C28H23NO4S2

M = 501.59

Triclinic,

a = 9.7485 (6) Å

b = 10.4930 (6) Å

c = 12.2879 (6) Å

α = 94.479 (3)°

β = 96.926 (3)°

γ = 102.253 (3)°

V = 1212.36 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 295 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.932, T max = 0.946

28630 measured reflections

5104 independent reflections

3744 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.109

S = 1.07

5104 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; 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 (Sheldrick, 2008 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015019428/hb7517sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019428/hb7517Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015019428/hb7517Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015019428/hb7517fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015019428/hb7517fig2.tif

The crystal packing of the title compound, viewed along the a axis. The C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in these inter­actions have been omitted for clarity.

CCDC reference: 1431246

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H23NO4S2	Z = 2
Mr = 501.59	F(000) = 524
Triclinic, P1	Dx = 1.374 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7485 (6) Å	Cell parameters from 9872 reflections
b = 10.4930 (6) Å	θ = 2.2–26.6°
c = 12.2879 (6) Å	µ = 0.26 mm−1
α = 94.479 (3)°	T = 295 K
β = 96.926 (3)°	Block, colourless
γ = 102.253 (3)°	0.28 × 0.24 × 0.22 mm
V = 1212.36 (12) Å3

Bruker Kappa APEXII CCD diffractometer	5104 independent reflections
Radiation source: fine-focus sealed tube	3744 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scan	θmax = 26.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.932, Tmax = 0.946	k = −13→13
28630 measured reflections	l = −15→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0176P)2 + 1.3407P] where P = (Fo2 + 2Fc2)/3
5104 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.7800 (2)	0.2579 (2)	0.49099 (18)	0.0381 (5)
C2	0.7195 (3)	0.1253 (3)	0.4812 (2)	0.0536 (7)
H2	0.7028	0.0754	0.4130	0.064*
C3	0.6844 (4)	0.0681 (3)	0.5743 (3)	0.0672 (8)
H3	0.6431	−0.0210	0.5690	0.081*
C4	0.7100 (4)	0.1417 (4)	0.6744 (2)	0.0721 (10)
H4	0.6871	0.1024	0.7370	0.087*
C5	0.7693 (4)	0.2735 (4)	0.6827 (2)	0.0719 (10)
H5	0.7856	0.3229	0.7511	0.086*
C6	0.8052 (3)	0.3336 (3)	0.5911 (2)	0.0551 (7)
H6	0.8454	0.4230	0.5967	0.066*
C7	0.5685 (2)	0.2997 (2)	0.28275 (18)	0.0364 (5)
C8	0.5302 (3)	0.3979 (3)	0.3462 (2)	0.0565 (7)
H8	0.5973	0.4611	0.3931	0.068*
C9	0.3882 (4)	0.3974 (3)	0.3363 (3)	0.0703 (9)
H9	0.3585	0.4615	0.3782	0.084*
C10	0.2879 (3)	0.3042 (4)	0.2659 (3)	0.0677 (9)
H10	0.1928	0.3073	0.2613	0.081*
C11	0.3263 (3)	0.2080 (3)	0.2032 (2)	0.0553 (7)
H11	0.2586	0.1460	0.1558	0.066*
C12	0.4692 (2)	0.2047 (2)	0.21191 (19)	0.0391 (5)
C13	0.5447 (2)	0.1211 (2)	0.15991 (19)	0.0395 (5)
H13	0.5040	0.0496	0.1080	0.047*
C14	0.6838 (2)	0.1612 (2)	0.19720 (17)	0.0321 (5)
C15	0.8030 (3)	0.1136 (2)	0.15503 (18)	0.0372 (5)
H15	0.8880	0.1440	0.2097	0.045*
C16	0.7758 (3)	−0.0364 (2)	0.1323 (2)	0.0487 (6)
H16A	0.6854	−0.0690	0.0857	0.058*
H16B	0.8492	−0.0592	0.0930	0.058*
C17	0.7744 (3)	−0.1007 (2)	0.2368 (2)	0.0464 (6)
C18	0.8982 (3)	−0.0935 (3)	0.3066 (3)	0.0713 (9)
H18	0.9838	−0.0485	0.2883	0.086*
C19	0.8969 (4)	−0.1517 (4)	0.4026 (3)	0.0884 (12)
H19	0.9814	−0.1445	0.4492	0.106*
C20	0.7738 (5)	−0.2196 (4)	0.4301 (3)	0.0833 (11)
H20	0.7741	−0.2610	0.4943	0.100*
C21	0.6501 (4)	−0.2271 (3)	0.3636 (3)	0.0746 (10)
H21	0.5652	−0.2719	0.3832	0.089*
C22	0.6499 (3)	−0.1682 (3)	0.2671 (2)	0.0588 (7)
H22	0.5646	−0.1742	0.2218	0.071*
C23	0.8138 (3)	0.3404 (2)	0.03825 (19)	0.0419 (6)
C24	0.9082 (3)	0.4365 (3)	0.1084 (2)	0.0544 (7)
H24	0.9866	0.4176	0.1494	0.065*
C25	0.8843 (4)	0.5624 (3)	0.1169 (3)	0.0716 (9)
H25	0.9450	0.6280	0.1661	0.086*
C26	0.7725 (4)	0.5902 (3)	0.0535 (3)	0.0803 (11)
H26	0.7580	0.6751	0.0589	0.096*
C27	0.6815 (4)	0.4954 (4)	−0.0176 (3)	0.0806 (10)
H27	0.6067	0.5161	−0.0619	0.097*
C28	0.7000 (3)	0.3684 (3)	−0.0244 (3)	0.0619 (8)
H28	0.6359	0.3025	−0.0710	0.074*
N1	0.70401 (19)	0.27497 (18)	0.27447 (14)	0.0333 (4)
O1	0.8486 (2)	0.46961 (17)	0.39621 (15)	0.0570 (5)
O2	0.95665 (17)	0.28679 (19)	0.34733 (14)	0.0507 (5)
O3	0.7321 (3)	0.10587 (19)	−0.05895 (15)	0.0762 (7)
O4	0.9842 (3)	0.1806 (2)	0.0183 (2)	0.0821 (8)
S1	0.83746 (6)	0.33264 (6)	0.37640 (5)	0.03940 (15)
S2	0.83884 (8)	0.17893 (6)	0.02663 (5)	0.04973 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0340 (12)	0.0513 (14)	0.0312 (11)	0.0156 (11)	0.0035 (9)	0.0023 (10)
C2	0.0675 (19)	0.0548 (16)	0.0382 (14)	0.0107 (14)	0.0107 (13)	0.0056 (12)
C3	0.077 (2)	0.072 (2)	0.0570 (18)	0.0150 (17)	0.0192 (16)	0.0214 (16)
C4	0.066 (2)	0.117 (3)	0.0420 (16)	0.029 (2)	0.0174 (15)	0.0277 (18)
C5	0.068 (2)	0.115 (3)	0.0307 (14)	0.021 (2)	0.0085 (13)	−0.0044 (16)
C6	0.0494 (16)	0.0736 (19)	0.0405 (14)	0.0146 (14)	0.0069 (12)	−0.0086 (13)
C7	0.0376 (13)	0.0438 (13)	0.0325 (11)	0.0155 (10)	0.0081 (9)	0.0096 (10)
C8	0.0579 (18)	0.0594 (17)	0.0569 (17)	0.0269 (14)	0.0088 (14)	−0.0034 (13)
C9	0.072 (2)	0.080 (2)	0.076 (2)	0.0471 (19)	0.0254 (18)	0.0069 (18)
C10	0.0442 (17)	0.093 (2)	0.079 (2)	0.0337 (17)	0.0154 (16)	0.0245 (19)
C11	0.0361 (14)	0.0706 (19)	0.0612 (17)	0.0141 (13)	0.0068 (12)	0.0138 (15)
C12	0.0326 (12)	0.0494 (14)	0.0365 (12)	0.0084 (10)	0.0072 (10)	0.0110 (10)
C13	0.0374 (13)	0.0417 (13)	0.0357 (12)	0.0016 (10)	0.0060 (10)	0.0005 (10)
C14	0.0382 (12)	0.0329 (11)	0.0269 (10)	0.0084 (9)	0.0090 (9)	0.0053 (9)
C15	0.0406 (13)	0.0378 (12)	0.0351 (12)	0.0103 (10)	0.0118 (10)	0.0016 (10)
C16	0.0622 (17)	0.0389 (13)	0.0497 (15)	0.0161 (12)	0.0205 (13)	0.0010 (11)
C17	0.0542 (16)	0.0372 (13)	0.0540 (15)	0.0201 (12)	0.0144 (12)	0.0044 (11)
C18	0.0500 (18)	0.074 (2)	0.101 (3)	0.0284 (16)	0.0145 (17)	0.0323 (19)
C19	0.082 (3)	0.091 (3)	0.101 (3)	0.041 (2)	−0.008 (2)	0.037 (2)
C20	0.113 (3)	0.068 (2)	0.081 (2)	0.035 (2)	0.017 (2)	0.0373 (19)
C21	0.083 (2)	0.0584 (19)	0.085 (2)	0.0074 (17)	0.024 (2)	0.0262 (18)
C22	0.0602 (18)	0.0491 (16)	0.0636 (18)	0.0035 (14)	0.0073 (14)	0.0107 (14)
C23	0.0491 (15)	0.0422 (13)	0.0344 (12)	0.0027 (11)	0.0176 (11)	0.0066 (10)
C24	0.0609 (18)	0.0486 (16)	0.0498 (16)	0.0019 (13)	0.0098 (13)	0.0077 (12)
C25	0.095 (3)	0.0418 (16)	0.071 (2)	−0.0038 (17)	0.0230 (19)	0.0002 (15)
C26	0.096 (3)	0.054 (2)	0.103 (3)	0.027 (2)	0.042 (2)	0.017 (2)
C27	0.068 (2)	0.089 (3)	0.099 (3)	0.036 (2)	0.022 (2)	0.031 (2)
C28	0.0578 (18)	0.0658 (19)	0.0601 (18)	0.0080 (15)	0.0097 (15)	0.0074 (15)
N1	0.0338 (10)	0.0360 (10)	0.0296 (9)	0.0078 (8)	0.0050 (8)	0.0000 (8)
O1	0.0690 (13)	0.0390 (10)	0.0527 (11)	−0.0034 (9)	0.0004 (9)	−0.0035 (8)
O2	0.0323 (9)	0.0753 (13)	0.0435 (10)	0.0100 (9)	0.0073 (7)	0.0017 (9)
O3	0.128 (2)	0.0516 (12)	0.0348 (10)	−0.0095 (12)	0.0162 (11)	−0.0058 (9)
O4	0.0838 (16)	0.0688 (14)	0.1168 (19)	0.0287 (12)	0.0735 (15)	0.0273 (13)
S1	0.0369 (3)	0.0433 (3)	0.0340 (3)	0.0025 (3)	0.0040 (2)	−0.0011 (2)
S2	0.0668 (5)	0.0409 (3)	0.0434 (4)	0.0055 (3)	0.0289 (3)	0.0016 (3)

C1—C6	1.376 (3)	C16—C17	1.497 (4)
C1—C2	1.381 (4)	C16—H16A	0.9700
C1—S1	1.757 (2)	C16—H16B	0.9700
C2—C3	1.379 (4)	C17—C18	1.377 (4)
C2—H2	0.9300	C17—C22	1.378 (4)
C3—C4	1.366 (4)	C18—C19	1.370 (5)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.371 (5)	C19—C20	1.355 (5)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.379 (4)	C20—C21	1.356 (5)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.380 (4)
C7—C8	1.385 (3)	C21—H21	0.9300
C7—C12	1.392 (3)	C22—H22	0.9300
C7—N1	1.413 (3)	C23—C28	1.370 (4)
C8—C9	1.374 (4)	C23—C24	1.373 (4)
C8—H8	0.9300	C23—S2	1.760 (3)
C9—C10	1.385 (5)	C24—C25	1.387 (4)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.365 (4)	C25—C26	1.358 (5)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.392 (3)	C26—C27	1.357 (5)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.421 (3)	C27—C28	1.379 (5)
C13—C14	1.343 (3)	C27—H27	0.9300
C13—H13	0.9300	C28—H28	0.9300
C14—N1	1.429 (3)	N1—S1	1.6679 (18)
C14—C15	1.490 (3)	O1—S1	1.4176 (18)
C15—C16	1.536 (3)	O2—S1	1.4211 (18)
C15—S2	1.812 (2)	O3—S2	1.431 (2)
C15—H15	0.9800	O4—S2	1.430 (2)
C6—C1—C2	121.5 (2)	H16A—C16—H16B	108.0
C6—C1—S1	118.0 (2)	C18—C17—C22	117.7 (3)
C2—C1—S1	120.35 (18)	C18—C17—C16	120.9 (3)
C3—C2—C1	118.9 (3)	C22—C17—C16	121.4 (3)
C3—C2—H2	120.6	C19—C18—C17	120.9 (3)
C1—C2—H2	120.6	C19—C18—H18	119.5
C4—C3—C2	120.3 (3)	C17—C18—H18	119.5
C4—C3—H3	119.9	C20—C19—C18	120.6 (3)
C2—C3—H3	119.9	C20—C19—H19	119.7
C3—C4—C5	120.2 (3)	C18—C19—H19	119.7
C3—C4—H4	119.9	C19—C20—C21	119.8 (3)
C5—C4—H4	119.9	C19—C20—H20	120.1
C4—C5—C6	120.8 (3)	C21—C20—H20	120.1
C4—C5—H5	119.6	C20—C21—C22	120.1 (3)
C6—C5—H5	119.6	C20—C21—H21	119.9
C1—C6—C5	118.3 (3)	C22—C21—H21	119.9
C1—C6—H6	120.9	C17—C22—C21	120.8 (3)
C5—C6—H6	120.9	C17—C22—H22	119.6
C8—C7—C12	122.3 (2)	C21—C22—H22	119.6
C8—C7—N1	129.9 (2)	C28—C23—C24	120.9 (3)
C12—C7—N1	107.88 (19)	C28—C23—S2	119.0 (2)
C9—C8—C7	116.6 (3)	C24—C23—S2	120.1 (2)
C9—C8—H8	121.7	C23—C24—C25	118.7 (3)
C7—C8—H8	121.7	C23—C24—H24	120.7
C8—C9—C10	122.0 (3)	C25—C24—H24	120.7
C8—C9—H9	119.0	C26—C25—C24	120.2 (3)
C10—C9—H9	119.0	C26—C25—H25	119.9
C11—C10—C9	121.1 (3)	C24—C25—H25	119.9
C11—C10—H10	119.4	C27—C26—C25	120.8 (3)
C9—C10—H10	119.4	C27—C26—H26	119.6
C10—C11—C12	118.5 (3)	C25—C26—H26	119.6
C10—C11—H11	120.7	C26—C27—C28	120.1 (3)
C12—C11—H11	120.7	C26—C27—H27	120.0
C11—C12—C7	119.5 (2)	C28—C27—H27	120.0
C11—C12—C13	133.2 (2)	C23—C28—C27	119.3 (3)
C7—C12—C13	107.3 (2)	C23—C28—H28	120.4
C14—C13—C12	109.5 (2)	C27—C28—H28	120.4
C14—C13—H13	125.2	C7—N1—C14	106.97 (18)
C12—C13—H13	125.2	C7—N1—S1	120.12 (15)
C13—C14—N1	108.34 (19)	C14—N1—S1	128.16 (15)
C13—C14—C15	127.7 (2)	O1—S1—O2	118.97 (12)
N1—C14—C15	123.26 (19)	O1—S1—N1	107.18 (11)
C14—C15—C16	114.0 (2)	O2—S1—N1	107.21 (10)
C14—C15—S2	110.79 (16)	O1—S1—C1	108.76 (11)
C16—C15—S2	106.56 (15)	O2—S1—C1	109.44 (11)
C14—C15—H15	108.4	N1—S1—C1	104.28 (10)
C16—C15—H15	108.4	O4—S2—O3	118.72 (15)
S2—C15—H15	108.4	O4—S2—C23	109.84 (12)
C17—C16—C15	111.6 (2)	O3—S2—C23	106.77 (14)
C17—C16—H16A	109.3	O4—S2—C15	106.67 (13)
C15—C16—H16A	109.3	O3—S2—C15	107.65 (11)
C17—C16—H16B	109.3	C23—S2—C15	106.58 (10)
C15—C16—H16B	109.3
C6—C1—C2—C3	−0.2 (4)	S2—C23—C24—C25	−179.1 (2)
S1—C1—C2—C3	175.7 (2)	C23—C24—C25—C26	−2.5 (5)
C1—C2—C3—C4	−0.4 (5)	C24—C25—C26—C27	0.9 (5)
C2—C3—C4—C5	0.8 (5)	C25—C26—C27—C28	1.5 (6)
C3—C4—C5—C6	−0.6 (5)	C24—C23—C28—C27	0.8 (4)
C2—C1—C6—C5	0.4 (4)	S2—C23—C28—C27	−178.5 (2)
S1—C1—C6—C5	−175.5 (2)	C26—C27—C28—C23	−2.4 (5)
C4—C5—C6—C1	0.0 (5)	C8—C7—N1—C14	179.9 (2)
C12—C7—C8—C9	0.2 (4)	C12—C7—N1—C14	−0.6 (2)
N1—C7—C8—C9	179.6 (3)	C8—C7—N1—S1	22.4 (3)
C7—C8—C9—C10	−0.5 (5)	C12—C7—N1—S1	−158.08 (16)
C8—C9—C10—C11	0.2 (5)	C13—C14—N1—C7	0.9 (2)
C9—C10—C11—C12	0.4 (5)	C15—C14—N1—C7	171.90 (19)
C10—C11—C12—C7	−0.7 (4)	C13—C14—N1—S1	156.01 (17)
C10—C11—C12—C13	−179.6 (3)	C15—C14—N1—S1	−33.0 (3)
C8—C7—C12—C11	0.4 (4)	C7—N1—S1—O1	−54.17 (19)
N1—C7—C12—C11	−179.1 (2)	C14—N1—S1—O1	153.59 (18)
C8—C7—C12—C13	179.6 (2)	C7—N1—S1—O2	177.05 (17)
N1—C7—C12—C13	0.1 (2)	C14—N1—S1—O2	24.8 (2)
C11—C12—C13—C14	179.5 (3)	C7—N1—S1—C1	61.05 (19)
C7—C12—C13—C14	0.5 (3)	C14—N1—S1—C1	−91.20 (19)
C12—C13—C14—N1	−0.9 (3)	C6—C1—S1—O1	−23.8 (2)
C12—C13—C14—C15	−171.4 (2)	C2—C1—S1—O1	160.2 (2)
C13—C14—C15—C16	−44.7 (3)	C6—C1—S1—O2	107.6 (2)
N1—C14—C15—C16	146.1 (2)	C2—C1—S1—O2	−68.4 (2)
C13—C14—C15—S2	75.5 (3)	C6—C1—S1—N1	−137.9 (2)
N1—C14—C15—S2	−93.7 (2)	C2—C1—S1—N1	46.1 (2)
C14—C15—C16—C17	−69.2 (3)	C28—C23—S2—O4	134.5 (2)
S2—C15—C16—C17	168.22 (19)	C24—C23—S2—O4	−44.9 (2)
C15—C16—C17—C18	−72.9 (3)	C28—C23—S2—O3	4.5 (2)
C15—C16—C17—C22	106.7 (3)	C24—C23—S2—O3	−174.8 (2)
C22—C17—C18—C19	0.1 (5)	C28—C23—S2—C15	−110.3 (2)
C16—C17—C18—C19	179.6 (3)	C24—C23—S2—C15	70.3 (2)
C17—C18—C19—C20	1.1 (6)	C14—C15—S2—O4	154.36 (17)
C18—C19—C20—C21	−1.9 (6)	C16—C15—S2—O4	−81.1 (2)
C19—C20—C21—C22	1.5 (6)	C14—C15—S2—O3	−77.20 (19)
C18—C17—C22—C21	−0.4 (4)	C16—C15—S2—O3	47.4 (2)
C16—C17—C22—C21	−180.0 (3)	C14—C15—S2—C23	37.04 (19)
C20—C21—C22—C17	−0.3 (5)	C16—C15—S2—C23	161.59 (17)
C28—C23—C24—C25	1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.43	3.009 (4)	121
C15—H15···O2	0.98	2.11	2.907 (3)	137
C4—H4···O3i	0.93	2.49	3.314 (3)	148
C13—H13···O3ii	0.93	2.50	3.240 (3)	137
C2—H2···Cg4	0.93	2.83	3.544 (3)	134
C19—H19···Cg2iii	0.93	2.91	3.620 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C1–C6 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.93	2.43	3.009 (4)	121
C15—H15⋯O2	0.98	2.11	2.907 (3)	137
C4—H4⋯O3i	0.93	2.49	3.314 (3)	148
C13—H13⋯O3ii	0.93	2.50	3.240 (3)	137
C2—H2⋯Cg4	0.93	2.83	3.544 (3)	134
C19—H19⋯Cg2iii	0.93	2.91	3.620 (4)	134

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