1,8-Bis(tos-yloxy)-9,10-anthraquinone.

In the crystal structure of the title compound, C(28)H(20)O(8)S(2), adjacent anthracene skeletons are parallel or inclined at an angle of 20.6 (1)°. In the mol-ecular structure, the mean plane of the anthracene skeleton makes dihedral angles of 49.6 (1) and 76.8 (1)° with the tosyl rings, and the two terminal benzene rings are oriented at an angle of 74.5 (1)° with respect to each other. The crystal structure is stabilized by inter-molecular C-H⋯O and C-O⋯π inter-actions.

Related literature

For general background to anthraquinones, see: Cheng & Zee-Cheng (1983 ▶); Dzierzbicka et al. (2006 ▶); Gatto et al. (1996 ▶); Hunger (2003 ▶); Krapcho et al. (1991 ▶); Nakanishi et al. (2005 ▶); Zielske (1987 ▶); Zon et al. (2003 ▶). For related structures, see: Sereda & Akhvlediani (2003 ▶); Slouf (2002 ▶); Zain & Ng (2005 ▶). For mol­ecular inter­actions, see: Bianchi et al. (2004 ▶); Santos-Contreras et al. (2007 ▶); Spek (2009 ▶); Steiner (1999 ▶). For the synthesis, see: Ossowski et al. (2000 ▶).

Experimental

Crystal data

C28H20O8S2

M = 548.58

Monoclinic,

a = 8.263 (2) Å

b = 27.473 (5) Å

c = 11.162 (2) Å

β = 100.36 (3)°

V = 2492.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 295 K

0.4 × 0.3 × 0.15 mm

Data collection

Oxford Diffraction Gemini R ULTRA Ruby CCD diffractometer

18048 measured reflections

4371 independent reflections

3374 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.163

S = 1.15

4371 reflections

345 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051009/xu2694sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051009/xu2694Isup2.hkl

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

C28H20O8S2	F(000) = 1136
Mr = 548.58	Dx = 1.462 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10108 reflections
a = 8.263 (2) Å	θ = 3.2–29.2°
b = 27.473 (5) Å	µ = 0.27 mm−1
c = 11.162 (2) Å	T = 295 K
β = 100.36 (3)°	Block, yellow
V = 2492.6 (9) Å3	0.4 × 0.3 × 0.15 mm
Z = 4

Oxford Diffraction Gemini R ULTRA Ruby CCD diffractometer	3374 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.050
graphite	θmax = 25.1°, θmin = 3.2°
Detector resolution: 10.4002 pixels mm-1	h = −9→9
ω scans	k = −28→32
18048 measured reflections	l = −13→11
4371 independent 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0997P)2 + 0.3332P] where P = (Fo2 + 2Fc2)/3
4371 reflections	(Δ/σ)max = 0.002
345 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.1135 (3)	0.52337 (10)	0.7763 (2)	0.0427 (6)
C2	0.0657 (4)	0.47974 (11)	0.8207 (3)	0.0575 (8)
H2	0.0301	0.4789	0.8951	0.069*
C3	0.0707 (4)	0.43742 (11)	0.7550 (3)	0.0636 (9)
H3	0.0365	0.4082	0.7843	0.076*
C4	0.1262 (4)	0.43846 (11)	0.6463 (3)	0.0548 (8)
H4	0.1311	0.4098	0.6027	0.066*
C5	0.3761 (3)	0.52607 (12)	0.3386 (2)	0.0511 (7)
H5	0.3765	0.4972	0.2949	0.061*
C6	0.4458 (4)	0.56703 (12)	0.3008 (3)	0.0560 (8)
H6	0.4921	0.5660	0.2308	0.067*
C7	0.4480 (4)	0.60985 (11)	0.3654 (3)	0.0518 (7)
H7	0.5004	0.6372	0.3415	0.062*
C8	0.3724 (3)	0.61198 (10)	0.4653 (2)	0.0412 (6)
C9	0.2008 (3)	0.57330 (9)	0.6073 (2)	0.0393 (6)
C10	0.2362 (3)	0.48179 (10)	0.4841 (3)	0.0469 (7)
C11	0.1676 (3)	0.52607 (9)	0.6648 (2)	0.0391 (6)
C12	0.1754 (3)	0.48225 (9)	0.6010 (3)	0.0430 (6)
C13	0.2964 (3)	0.57106 (9)	0.5061 (2)	0.0385 (6)
C14	0.3048 (3)	0.52732 (10)	0.4419 (2)	0.0419 (6)
O15	0.0972 (2)	0.56551 (7)	0.84323 (17)	0.0486 (5)
S16	0.22980 (10)	0.57749 (3)	0.96370 (6)	0.0532 (3)
O17	0.1499 (3)	0.61401 (9)	1.0209 (2)	0.0762 (7)
O18	0.2768 (3)	0.53273 (8)	1.02503 (19)	0.0653 (6)
C19	0.3976 (3)	0.60173 (10)	0.9090 (2)	0.0449 (6)
C20	0.3917 (4)	0.64943 (11)	0.8680 (3)	0.0541 (8)
H20	0.3000	0.6687	0.8712	0.065*
C21	0.5222 (4)	0.66780 (11)	0.8228 (3)	0.0540 (8)
H21	0.5183	0.6998	0.7955	0.065*
C22	0.6606 (4)	0.63985 (11)	0.8167 (3)	0.0546 (7)
C23	0.6631 (4)	0.59232 (11)	0.8589 (3)	0.0644 (9)
H23	0.7547	0.5730	0.8561	0.077*
C24	0.5337 (4)	0.57324 (11)	0.9046 (3)	0.0582 (8)
H24	0.5376	0.5413	0.9325	0.070*
C25	0.8010 (5)	0.66019 (14)	0.7636 (4)	0.0856 (12)
H25A	0.8561	0.6342	0.7297	0.128*
H25B	0.8771	0.6762	0.8264	0.128*
H25C	0.7595	0.6832	0.7007	0.128*
O26	0.1427 (3)	0.61106 (7)	0.63596 (19)	0.0530 (5)
O27	0.2365 (3)	0.44406 (8)	0.4261 (2)	0.0714 (7)
O28	0.3778 (2)	0.65378 (6)	0.53713 (16)	0.0471 (5)
S29	0.34049 (9)	0.70699 (2)	0.48060 (7)	0.0481 (2)
O30	0.3284 (3)	0.73551 (8)	0.5843 (2)	0.0638 (6)
O31	0.4611 (3)	0.71850 (8)	0.4092 (2)	0.0643 (6)
C32	0.1493 (3)	0.70184 (10)	0.3851 (3)	0.0444 (6)
C33	0.1394 (4)	0.70045 (11)	0.2604 (3)	0.0556 (8)
H33	0.2343	0.7015	0.2266	0.067*
C34	−0.0135 (4)	0.69754 (12)	0.1866 (3)	0.0586 (8)
H34	−0.0206	0.6962	0.1026	0.070*
C35	−0.1561 (4)	0.69661 (10)	0.2349 (3)	0.0525 (7)
C36	−0.1428 (4)	0.69827 (11)	0.3605 (3)	0.0533 (7)
H36	−0.2380	0.6979	0.3941	0.064*
C37	0.0083 (3)	0.70044 (10)	0.4368 (3)	0.0488 (7)
H37	0.0156	0.7010	0.5209	0.059*
C38	−0.3217 (5)	0.69311 (16)	0.1525 (4)	0.0821 (11)
H38A	−0.3199	0.7114	0.0795	0.123*
H38B	−0.4047	0.7061	0.1936	0.123*
H38C	−0.3458	0.6596	0.1320	0.123*

	U11	U22	U33	U12	U13	U23
C1	0.0381 (14)	0.0445 (15)	0.0461 (15)	0.0029 (11)	0.0092 (11)	0.0010 (12)
C2	0.0600 (18)	0.0551 (18)	0.0611 (19)	−0.0041 (14)	0.0213 (15)	0.0089 (15)
C3	0.065 (2)	0.0446 (17)	0.083 (2)	−0.0099 (14)	0.0186 (18)	0.0101 (16)
C4	0.0511 (16)	0.0393 (15)	0.072 (2)	−0.0036 (12)	0.0054 (15)	−0.0027 (14)
C5	0.0485 (16)	0.0628 (19)	0.0408 (16)	0.0076 (13)	0.0051 (12)	−0.0107 (13)
C6	0.0539 (17)	0.077 (2)	0.0393 (16)	0.0067 (15)	0.0131 (13)	−0.0016 (14)
C7	0.0536 (16)	0.0576 (18)	0.0457 (16)	0.0011 (13)	0.0127 (13)	0.0055 (13)
C8	0.0388 (13)	0.0450 (15)	0.0383 (14)	0.0039 (11)	0.0029 (11)	0.0020 (11)
C9	0.0376 (13)	0.0422 (14)	0.0372 (14)	0.0016 (11)	0.0045 (11)	−0.0010 (11)
C10	0.0436 (14)	0.0440 (16)	0.0504 (16)	0.0015 (11)	0.0017 (12)	−0.0101 (13)
C11	0.0345 (13)	0.0406 (14)	0.0412 (14)	0.0019 (10)	0.0046 (10)	0.0015 (11)
C12	0.0365 (13)	0.0406 (15)	0.0504 (16)	0.0005 (11)	0.0041 (11)	−0.0014 (12)
C13	0.0364 (13)	0.0456 (14)	0.0321 (13)	0.0053 (11)	0.0029 (10)	0.0001 (11)
C14	0.0381 (13)	0.0480 (15)	0.0375 (14)	0.0056 (11)	0.0010 (11)	−0.0053 (12)
O15	0.0510 (11)	0.0515 (11)	0.0462 (11)	0.0089 (8)	0.0163 (9)	0.0006 (8)
S16	0.0651 (5)	0.0582 (5)	0.0396 (4)	0.0068 (3)	0.0181 (3)	−0.0027 (3)
O17	0.0945 (18)	0.0811 (17)	0.0624 (14)	0.0122 (13)	0.0391 (13)	−0.0169 (12)
O18	0.0802 (15)	0.0693 (14)	0.0469 (12)	0.0063 (11)	0.0126 (11)	0.0156 (10)
C19	0.0543 (16)	0.0428 (15)	0.0372 (14)	0.0068 (12)	0.0070 (12)	−0.0058 (11)
C20	0.0512 (17)	0.0468 (16)	0.0612 (19)	0.0107 (13)	0.0018 (14)	−0.0073 (14)
C21	0.0632 (19)	0.0402 (15)	0.0557 (18)	0.0016 (13)	0.0025 (15)	−0.0025 (13)
C22	0.0587 (18)	0.0450 (16)	0.0602 (18)	−0.0005 (13)	0.0111 (15)	−0.0095 (13)
C23	0.060 (2)	0.0445 (18)	0.092 (3)	0.0124 (14)	0.0231 (17)	−0.0039 (16)
C24	0.066 (2)	0.0404 (16)	0.070 (2)	0.0106 (14)	0.0173 (16)	0.0004 (14)
C25	0.084 (3)	0.064 (2)	0.118 (3)	−0.0084 (19)	0.044 (2)	−0.004 (2)
O26	0.0669 (13)	0.0389 (11)	0.0587 (12)	0.0081 (9)	0.0259 (10)	0.0001 (9)
O27	0.0901 (17)	0.0553 (13)	0.0714 (15)	−0.0082 (11)	0.0213 (13)	−0.0257 (12)
O28	0.0543 (11)	0.0439 (11)	0.0429 (11)	−0.0036 (8)	0.0085 (8)	0.0006 (8)
S29	0.0439 (4)	0.0417 (4)	0.0596 (5)	−0.0070 (3)	0.0114 (3)	0.0020 (3)
O30	0.0678 (14)	0.0496 (12)	0.0720 (14)	−0.0069 (10)	0.0070 (11)	−0.0169 (10)
O31	0.0490 (12)	0.0625 (14)	0.0855 (16)	−0.0099 (10)	0.0230 (11)	0.0141 (12)
C32	0.0452 (15)	0.0402 (14)	0.0500 (16)	0.0007 (11)	0.0143 (12)	0.0055 (12)
C33	0.0544 (17)	0.0613 (18)	0.0564 (18)	0.0063 (14)	0.0241 (14)	0.0098 (14)
C34	0.069 (2)	0.0629 (19)	0.0436 (16)	0.0113 (15)	0.0102 (15)	0.0056 (14)
C35	0.0535 (17)	0.0416 (15)	0.0605 (19)	0.0073 (12)	0.0050 (14)	0.0021 (13)
C36	0.0437 (16)	0.0584 (18)	0.0600 (19)	0.0032 (13)	0.0156 (14)	0.0024 (14)
C37	0.0483 (15)	0.0535 (17)	0.0469 (16)	−0.0007 (12)	0.0144 (12)	0.0011 (13)
C38	0.066 (2)	0.099 (3)	0.073 (2)	0.010 (2)	−0.0094 (18)	−0.001 (2)

C1—C2	1.382 (4)	C19—C20	1.386 (4)
C1—O15	1.398 (3)	C20—C21	1.367 (5)
C1—C11	1.398 (4)	C20—H20	0.9300
C2—C3	1.379 (5)	C21—C22	1.389 (4)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.372 (5)	C22—C23	1.387 (4)
C3—H3	0.9300	C22—C25	1.502 (5)
C4—C12	1.394 (4)	C23—C24	1.369 (5)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.364 (5)	C24—H24	0.9300
C5—C14	1.387 (4)	C25—H25A	0.9600
C5—H5	0.9300	C25—H25B	0.9600
C6—C7	1.379 (4)	C25—H25C	0.9600
C6—H6	0.9300	O28—S29	1.6000 (19)
C7—C8	1.373 (4)	S29—O30	1.416 (2)
C7—H7	0.9300	S29—O31	1.419 (2)
C8—O28	1.397 (3)	S29—C32	1.745 (3)
C8—C13	1.403 (4)	C32—C33	1.380 (4)
C9—O26	1.210 (3)	C32—C37	1.390 (4)
C9—C13	1.491 (4)	C33—C34	1.381 (4)
C9—C11	1.495 (4)	C33—H33	0.9300
C10—O27	1.223 (3)	C34—C35	1.381 (5)
C10—C12	1.479 (4)	C34—H34	0.9300
C10—C14	1.485 (4)	C35—C36	1.387 (4)
C11—C12	1.406 (4)	C35—C38	1.508 (4)
C13—C14	1.407 (4)	C36—C37	1.380 (4)
O15—S16	1.608 (2)	C36—H36	0.9300
S16—O17	1.415 (2)	C37—H37	0.9300
S16—O18	1.427 (2)	C38—H38A	0.9600
S16—C19	1.745 (3)	C38—H38B	0.9600
C19—C24	1.378 (4)	C38—H38C	0.9600
C2—C1—O15	117.8 (3)	C21—C20—C19	119.2 (3)
C2—C1—C11	121.6 (3)	C21—C20—H20	120.4
O15—C1—C11	120.6 (2)	C19—C20—H20	120.4
C3—C2—C1	120.2 (3)	C20—C21—C22	121.7 (3)
C3—C2—H2	119.9	C20—C21—H21	119.2
C1—C2—H2	119.9	C22—C21—H21	119.2
C4—C3—C2	119.9 (3)	C23—C22—C21	117.7 (3)
C4—C3—H3	120.0	C23—C22—C25	121.3 (3)
C2—C3—H3	120.0	C21—C22—C25	121.0 (3)
C3—C4—C12	120.3 (3)	C24—C23—C22	121.5 (3)
C3—C4—H4	119.8	C24—C23—H23	119.3
C12—C4—H4	119.8	C22—C23—H23	119.3
C6—C5—C14	120.2 (3)	C23—C24—C19	119.5 (3)
C6—C5—H5	119.9	C23—C24—H24	120.2
C14—C5—H5	119.9	C19—C24—H24	120.2
C5—C6—C7	120.6 (3)	C22—C25—H25A	109.5
C5—C6—H6	119.7	C22—C25—H25B	109.5
C7—C6—H6	119.7	H25A—C25—H25B	109.5
C8—C7—C6	119.7 (3)	C22—C25—H25C	109.5
C8—C7—H7	120.1	H25A—C25—H25C	109.5
C6—C7—H7	120.1	H25B—C25—H25C	109.5
C7—C8—O28	121.9 (2)	C8—O28—S29	122.72 (16)
C7—C8—C13	121.7 (3)	O30—S29—O31	119.70 (14)
O28—C8—C13	116.2 (2)	O30—S29—O28	102.71 (12)
O26—C9—C13	121.7 (2)	O31—S29—O28	108.68 (12)
O26—C9—C11	121.2 (2)	O30—S29—C32	110.80 (14)
C13—C9—C11	116.9 (2)	O31—S29—C32	108.96 (14)
O27—C10—C12	120.5 (3)	O28—S29—C32	104.82 (11)
O27—C10—C14	120.6 (3)	C33—C32—C37	121.0 (3)
C12—C10—C14	118.8 (2)	C33—C32—S29	120.1 (2)
C1—C11—C12	117.2 (2)	C37—C32—S29	118.9 (2)
C1—C11—C9	122.8 (2)	C32—C33—C34	119.0 (3)
C12—C11—C9	119.8 (2)	C32—C33—H33	120.5
C4—C12—C11	120.8 (3)	C34—C33—H33	120.5
C4—C12—C10	118.7 (3)	C33—C34—C35	121.4 (3)
C11—C12—C10	120.5 (2)	C33—C34—H34	119.3
C8—C13—C14	116.9 (2)	C35—C34—H34	119.3
C8—C13—C9	122.8 (2)	C34—C35—C36	118.4 (3)
C14—C13—C9	120.2 (2)	C34—C35—C38	120.5 (3)
C5—C14—C13	120.8 (3)	C36—C35—C38	121.1 (3)
C5—C14—C10	119.1 (2)	C37—C36—C35	121.5 (3)
C13—C14—C10	120.1 (2)	C37—C36—H36	119.2
C1—O15—S16	120.01 (16)	C35—C36—H36	119.2
O17—S16—O18	120.23 (15)	C36—C37—C32	118.6 (3)
O17—S16—O15	102.67 (14)	C36—C37—H37	120.7
O18—S16—O15	108.09 (12)	C32—C37—H37	120.7
O17—S16—C19	110.62 (15)	C35—C38—H38A	109.5
O18—S16—C19	109.39 (14)	C35—C38—H38B	109.5
O15—S16—C19	104.49 (12)	H38A—C38—H38B	109.5
C24—C19—C20	120.4 (3)	C35—C38—H38C	109.5
C24—C19—S16	120.0 (2)	H38A—C38—H38C	109.5
C20—C19—S16	119.6 (2)	H38B—C38—H38C	109.5
O15—C1—C2—C3	176.5 (3)	C12—C10—C14—C13	−6.3 (4)
C11—C1—C2—C3	0.1 (4)	C2—C1—O15—S16	77.9 (3)
C1—C2—C3—C4	1.3 (5)	C11—C1—O15—S16	−105.6 (2)
C2—C3—C4—C12	−0.9 (5)	C1—O15—S16—O17	−165.1 (2)
C14—C5—C6—C7	0.8 (4)	C1—O15—S16—O18	−37.1 (2)
C5—C6—C7—C8	−3.2 (4)	C1—O15—S16—C19	79.4 (2)
C6—C7—C8—O28	176.9 (2)	O17—S16—C19—C24	148.7 (2)
C6—C7—C8—C13	1.9 (4)	O18—S16—C19—C24	14.1 (3)
C2—C1—C11—C12	−1.6 (4)	O15—S16—C19—C24	−101.4 (2)
O15—C1—C11—C12	−177.9 (2)	O17—S16—C19—C20	−32.5 (3)
C2—C1—C11—C9	172.5 (2)	O18—S16—C19—C20	−167.1 (2)
O15—C1—C11—C9	−3.9 (4)	O15—S16—C19—C20	77.3 (2)
O26—C9—C11—C1	−19.9 (4)	C24—C19—C20—C21	0.2 (4)
C13—C9—C11—C1	165.1 (2)	S16—C19—C20—C21	−178.6 (2)
O26—C9—C11—C12	154.0 (3)	C19—C20—C21—C22	0.2 (5)
C13—C9—C11—C12	−21.0 (3)	C20—C21—C22—C23	−0.4 (5)
C3—C4—C12—C11	−0.7 (4)	C20—C21—C22—C25	178.3 (3)
C3—C4—C12—C10	179.4 (3)	C21—C22—C23—C24	0.3 (5)
C1—C11—C12—C4	1.9 (4)	C25—C22—C23—C24	−178.4 (4)
C9—C11—C12—C4	−172.4 (2)	C22—C23—C24—C19	0.0 (5)
C1—C11—C12—C10	−178.1 (2)	C20—C19—C24—C23	−0.3 (5)
C9—C11—C12—C10	7.6 (4)	S16—C19—C24—C23	178.5 (3)
O27—C10—C12—C4	3.1 (4)	C7—C8—O28—S29	47.3 (3)
C14—C10—C12—C4	−173.8 (2)	C13—C8—O28—S29	−137.4 (2)
O27—C10—C12—C11	−176.9 (2)	C8—O28—S29—O30	169.05 (19)
C14—C10—C12—C11	6.3 (4)	C8—O28—S29—O31	−63.2 (2)
C7—C8—C13—C14	1.6 (4)	C8—O28—S29—C32	53.2 (2)
O28—C8—C13—C14	−173.7 (2)	O30—S29—C32—C33	144.9 (2)
C7—C8—C13—C9	−174.4 (2)	O31—S29—C32—C33	11.2 (3)
O28—C8—C13—C9	10.3 (3)	O28—S29—C32—C33	−105.0 (2)
O26—C9—C13—C8	22.0 (4)	O30—S29—C32—C37	−33.5 (3)
C11—C9—C13—C8	−163.1 (2)	O31—S29—C32—C37	−167.2 (2)
O26—C9—C13—C14	−154.0 (2)	O28—S29—C32—C37	76.6 (2)
C11—C9—C13—C14	21.0 (3)	C37—C32—C33—C34	−0.1 (4)
C6—C5—C14—C13	2.8 (4)	S29—C32—C33—C34	−178.5 (2)
C6—C5—C14—C10	−177.4 (3)	C32—C33—C34—C35	0.8 (5)
C8—C13—C14—C5	−4.0 (3)	C33—C34—C35—C36	−0.5 (4)
C9—C13—C14—C5	172.2 (2)	C33—C34—C35—C38	−179.6 (3)
C8—C13—C14—C10	176.3 (2)	C34—C35—C36—C37	−0.5 (4)
C9—C13—C14—C10	−7.6 (3)	C38—C35—C36—C37	178.6 (3)
O27—C10—C14—C5	−2.9 (4)	C35—C36—C37—C32	1.1 (4)
C12—C10—C14—C5	173.9 (2)	C33—C32—C37—C36	−0.8 (4)
O27—C10—C14—C13	176.9 (2)	S29—C32—C37—C36	177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O18i	0.93	2.54	3.332 (4)	143
C33—H33···O30ii	0.93	2.56	3.241 (4)	130
C36—H36···O31iii	0.93	2.58	3.458 (4)	156

C	O	J	O···J	C···J	C–O···J
C10	O27	Cg1iv	3.688 (3)	3.481 (3)	70.71 (17)
C10	O27	Cg2v	3.452 (3)	3.528 (3)	83.41 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯O18i	0.93	2.54	3.332 (4)	143
C33—H33⋯O30ii	0.93	2.56	3.241 (4)	130
C36—H36⋯O31iii	0.93	2.58	3.458 (4)	156

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

Table 2

C–O⋯π inter­actions (Å,°).

C	O	J	O⋯J	C⋯J	C–O⋯J
C10	O27	Cg1iv	3.688 (3)	3.481 (3)	70.71 (17)
C10	O27	Cg2v	3.452 (3)	3.528 (3)	83.41 (18)

Symmetry codes: (iv) −x, −y + 1, −z + 1; (v) −x + 1, −y + 1, −z + 1. Cg1 and Cg2 are the centroids of the C1—C4/C11/C12 and C5—C8/C13/C14 rings respectively.