1,1'-(2,5-Dimethyl-thio-phene-3,4-di-yl)diethanone.

The title compound, C(10)H(12)O(2)S, crystallizes with four mol-ecules in the asymmetric unit. The main conformational difference between these mol-ecules is the orientation of the acetyl groups with respect to the ring. Whereas one acetyl group is only slightly twisted with respect to the thio-phene ring [C-C-C-O torsion angles = 165.7 (4), -164.6 (4), 164.3 (4) and -163.6 (4)°], the other acetyl group is markly twisted out of the ring plane [C-C-C-O torsion angles = -61.2 (6), 61.3 (7), -59.7 (7) and 59.9 (6)°]. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into infinite chains along the c axis.

Related literature

For the synthesis of the title compound, see: Li et al. (2011 ▶); Wang et al. (2004 ▶). For a related structure, see: Yu et al. (2010 ▶).

Experimental

Crystal data

C10H12O2S

M = 196.26

Monoclinic,

a = 12.142 (2) Å

b = 12.129 (2) Å

c = 27.446 (6) Å

β = 99.387 (2)°

V = 3987.8 (14) Å3

Z = 16

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.38 × 0.30 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.898, T max = 0.942

14665 measured reflections

7205 independent reflections

4969 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.092

S = 1.02

7205 reflections

485 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 3486 Friedel pairs

Flack parameter: 0.05 (7)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029710/bt5559sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029710/bt5559Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029710/bt5559Isup3.cml

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

C10H12O2S	Dx = 1.308 Mg m−3
Mr = 196.26	Melting point: 363 K
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 12.142 (2) Å	Cell parameters from 3384 reflections
b = 12.129 (2) Å	θ = 2.4–23.9°
c = 27.446 (6) Å	µ = 0.29 mm−1
β = 99.387 (2)°	T = 296 K
V = 3987.8 (14) Å3	Block, colourless
Z = 16	0.38 × 0.30 × 0.21 mm
F(000) = 1664

Bruker SMART APEXII CCD area-detector diffractometer	7205 independent reflections
Radiation source: fine-focus sealed tube	4969 reflections with I > 2σ(I)
graphite	Rint = 0.031
phi and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
Tmin = 0.898, Tmax = 0.942	k = −14→14
14665 measured reflections	l = −32→33

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0329P)2 + 1.3235P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
7205 reflections	Δρmax = 0.17 e Å−3
485 parameters	Δρmin = −0.23 e Å−3
2 restraints	Absolute structure: Flack (1983), 3486 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (7)

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.

	x	y	z	Uiso*/Ueq
C1	0.1299 (4)	0.1176 (4)	0.4644 (2)	0.0439 (13)
C2	0.0669 (4)	0.1446 (4)	0.4207 (2)	0.0401 (13)
C3	−0.0256 (4)	0.0686 (3)	0.40549 (18)	0.0402 (12)
C4	−0.0279 (3)	−0.0142 (3)	0.43893 (16)	0.0451 (10)
C5	0.2301 (5)	0.1710 (4)	0.4926 (2)	0.0554 (16)
H5A	0.2746	0.2015	0.4700	0.083*
H5B	0.2731	0.1173	0.5132	0.083*
H5C	0.2076	0.2287	0.5128	0.083*
C6	0.0987 (4)	0.2391 (4)	0.3911 (2)	0.0437 (13)
C7	−0.1085 (4)	0.0924 (4)	0.36101 (17)	0.0473 (10)
C8	−0.1080 (4)	−0.1097 (3)	0.44085 (17)	0.0620 (13)
H8A	−0.1834	−0.0828	0.4352	0.093*
H8B	−0.0927	−0.1441	0.4727	0.093*
H8C	−0.0985	−0.1626	0.4158	0.093*
C9	0.1385 (4)	0.2160 (4)	0.34303 (15)	0.0575 (12)
H9A	0.1178	0.2760	0.3206	0.086*
H9B	0.1049	0.1491	0.3290	0.086*
H9C	0.2182	0.2081	0.3488	0.086*
C10	−0.1952 (4)	0.0083 (4)	0.34150 (19)	0.0743 (15)
H10A	−0.2475	0.0008	0.3640	0.112*
H10B	−0.1598	−0.0614	0.3381	0.112*
H10C	−0.2339	0.0316	0.3099	0.112*
C11	0.2336 (3)	0.7569 (3)	0.43718 (15)	0.0421 (10)
C12	0.1384 (4)	0.7388 (4)	0.40351 (18)	0.0393 (12)
C13	0.0706 (4)	0.6523 (4)	0.4191 (2)	0.0379 (13)
C14	0.1126 (4)	0.6077 (4)	0.4636 (2)	0.0433 (13)
C15	0.3259 (4)	0.8407 (4)	0.43894 (17)	0.0675 (13)
H15A	0.3723	0.8218	0.4150	0.101*
H15B	0.3700	0.8411	0.4713	0.101*
H15C	0.2941	0.9124	0.4316	0.101*
C16	0.0998 (4)	0.8043 (3)	0.35802 (16)	0.0460 (10)
C17	−0.0341 (4)	0.6062 (4)	0.38910 (18)	0.0432 (12)
C18	0.0672 (5)	0.5167 (4)	0.4928 (2)	0.0597 (17)
H18A	0.0370	0.4588	0.4707	0.090*
H18B	0.0096	0.5460	0.5092	0.090*
H18C	0.1264	0.4877	0.5169	0.090*
C19	0.1763 (4)	0.8807 (4)	0.33769 (18)	0.0662 (13)
H19A	0.1419	0.9050	0.3055	0.099*
H19B	0.2448	0.8433	0.3353	0.099*
H19C	0.1915	0.9433	0.3591	0.099*
C20	−0.0254 (4)	0.5480 (4)	0.34209 (16)	0.0579 (12)
H20A	−0.0164	0.4704	0.3483	0.087*
H20B	0.0378	0.5756	0.3290	0.087*
H20C	−0.0922	0.5605	0.3187	0.087*
C21	0.3487 (3)	−0.0066 (3)	0.13375 (16)	0.0452 (10)
C22	0.4442 (4)	0.0093 (4)	0.16737 (18)	0.0397 (12)
C23	0.5136 (4)	0.0960 (4)	0.1516 (2)	0.0395 (14)
C24	0.4702 (4)	0.1402 (4)	0.1073 (2)	0.0412 (13)
C25	0.2538 (4)	−0.0864 (4)	0.13179 (18)	0.0595 (12)
H25A	0.2771	−0.1578	0.1223	0.089*
H25B	0.1918	−0.0614	0.1081	0.089*
H25C	0.2317	−0.0911	0.1638	0.089*
C26	0.4849 (4)	−0.0570 (3)	0.21115 (17)	0.0468 (10)
C27	0.6200 (4)	0.1393 (4)	0.18038 (19)	0.0457 (13)
C28	0.5153 (5)	0.2308 (5)	0.0799 (2)	0.0621 (17)
H28A	0.4779	0.2985	0.0851	0.093*
H28B	0.5034	0.2137	0.0452	0.093*
H28C	0.5939	0.2387	0.0915	0.093*
C29	0.4078 (4)	−0.1369 (4)	0.23122 (17)	0.0653 (13)
H29A	0.3862	−0.1943	0.2075	0.098*
H29B	0.3425	−0.0985	0.2375	0.098*
H29C	0.4457	−0.1687	0.2614	0.098*
C30	0.6137 (4)	0.1957 (3)	0.22774 (17)	0.0581 (12)
H30A	0.6874	0.2024	0.2465	0.087*
H30B	0.5677	0.1535	0.2462	0.087*
H30C	0.5820	0.2677	0.2212	0.087*
C31	−0.0373 (4)	0.1242 (4)	0.1086 (2)	0.0409 (13)
C32	0.0215 (4)	0.0999 (4)	0.1535 (2)	0.0373 (13)
C33	0.1135 (4)	0.1744 (3)	0.16831 (18)	0.0390 (12)
C34	0.1199 (3)	0.2560 (3)	0.13392 (15)	0.0438 (10)
C35	−0.1391 (5)	0.0656 (4)	0.0813 (2)	0.0583 (17)
H35A	−0.1332	−0.0119	0.0883	0.087*
H35B	−0.1435	0.0773	0.0464	0.087*
H35C	−0.2050	0.0943	0.0919	0.087*
C36	−0.0130 (4)	0.0059 (4)	0.1833 (2)	0.0445 (13)
C37	0.1960 (3)	0.1528 (4)	0.21315 (17)	0.0464 (10)
C38	0.1999 (4)	0.3480 (3)	0.13055 (18)	0.0620 (13)
H38A	0.2176	0.3837	0.1621	0.093*
H38B	0.1667	0.4004	0.1063	0.093*
H38C	0.2670	0.3191	0.1211	0.093*
C39	−0.0535 (4)	0.0325 (4)	0.22985 (16)	0.0580 (12)
H39A	−0.1235	0.0707	0.2225	0.087*
H39B	0.0001	0.0785	0.2500	0.087*
H39C	−0.0634	−0.0345	0.2473	0.087*
C40	0.2819 (3)	0.2373 (4)	0.23302 (17)	0.0615 (13)
H40A	0.3211	0.2133	0.2645	0.092*
H40B	0.2458	0.3064	0.2369	0.092*
H40C	0.3339	0.2461	0.2104	0.092*
O1	0.1038 (3)	0.3320 (2)	0.40784 (13)	0.0705 (9)
O2	−0.1062 (2)	0.1817 (3)	0.34011 (12)	0.0668 (9)
O3	0.0032 (3)	0.7933 (3)	0.33761 (11)	0.0626 (9)
O4	−0.1202 (2)	0.6078 (3)	0.40579 (13)	0.0688 (9)
O5	0.5817 (3)	−0.0474 (2)	0.23140 (12)	0.0665 (9)
O6	0.7055 (2)	0.1377 (3)	0.16305 (12)	0.0677 (9)
O7	−0.0166 (3)	−0.0868 (2)	0.16659 (12)	0.0658 (8)
O8	0.1926 (2)	0.0637 (2)	0.23397 (12)	0.0605 (8)
S1	0.07809 (11)	−0.00057 (11)	0.48785 (5)	0.0531 (4)
S2	0.23678 (11)	0.67089 (12)	0.48713 (5)	0.0541 (4)
S3	0.34281 (10)	0.08175 (12)	0.08483 (5)	0.0522 (4)
S4	0.01417 (10)	0.23984 (11)	0.08442 (5)	0.0525 (4)

	U11	U22	U33	U12	U13	U23
C1	0.043 (3)	0.049 (3)	0.041 (3)	−0.005 (2)	0.011 (2)	0.004 (3)
C2	0.041 (3)	0.040 (3)	0.041 (4)	−0.005 (3)	0.010 (3)	−0.001 (3)
C3	0.036 (2)	0.040 (3)	0.046 (3)	−0.002 (2)	0.009 (2)	−0.003 (2)
C4	0.046 (2)	0.040 (2)	0.052 (3)	−0.0078 (19)	0.015 (2)	−0.003 (2)
C5	0.049 (3)	0.073 (3)	0.043 (4)	−0.018 (3)	0.006 (3)	−0.005 (3)
C6	0.034 (3)	0.043 (3)	0.053 (3)	−0.002 (2)	0.005 (2)	0.003 (2)
C7	0.039 (2)	0.051 (3)	0.053 (3)	0.001 (2)	0.010 (2)	−0.002 (2)
C8	0.066 (3)	0.053 (3)	0.071 (3)	−0.023 (2)	0.025 (3)	0.003 (2)
C9	0.057 (3)	0.062 (3)	0.056 (3)	0.002 (2)	0.015 (2)	0.009 (2)
C10	0.050 (3)	0.087 (4)	0.078 (4)	−0.015 (3)	−0.012 (3)	0.000 (3)
C11	0.039 (2)	0.045 (2)	0.044 (2)	−0.0095 (19)	0.0109 (19)	−0.005 (2)
C12	0.040 (3)	0.036 (2)	0.042 (3)	−0.003 (2)	0.008 (2)	−0.0013 (19)
C13	0.040 (3)	0.034 (3)	0.039 (3)	−0.005 (2)	0.005 (3)	−0.003 (2)
C14	0.044 (3)	0.043 (3)	0.042 (3)	−0.007 (2)	0.005 (3)	−0.003 (2)
C15	0.057 (3)	0.073 (3)	0.069 (3)	−0.030 (3)	0.002 (2)	−0.003 (3)
C16	0.051 (3)	0.041 (3)	0.046 (3)	0.009 (2)	0.009 (2)	0.006 (2)
C17	0.043 (3)	0.039 (3)	0.047 (3)	0.001 (2)	0.003 (2)	0.006 (2)
C18	0.070 (4)	0.061 (3)	0.049 (4)	−0.018 (3)	0.012 (3)	0.001 (3)
C19	0.069 (3)	0.057 (3)	0.072 (3)	−0.015 (2)	0.010 (3)	0.016 (3)
C20	0.059 (3)	0.058 (3)	0.052 (3)	−0.002 (2)	−0.004 (2)	−0.011 (2)
C21	0.041 (2)	0.043 (2)	0.053 (3)	−0.008 (2)	0.010 (2)	−0.007 (2)
C22	0.033 (3)	0.041 (3)	0.046 (3)	0.000 (2)	0.011 (2)	−0.003 (2)
C23	0.032 (3)	0.040 (3)	0.047 (4)	0.001 (2)	0.009 (3)	−0.006 (3)
C24	0.039 (3)	0.045 (3)	0.040 (3)	−0.008 (2)	0.008 (2)	−0.009 (3)
C25	0.048 (2)	0.061 (3)	0.072 (3)	−0.024 (2)	0.016 (2)	−0.004 (3)
C26	0.049 (3)	0.041 (3)	0.051 (3)	−0.004 (2)	0.011 (2)	−0.007 (2)
C27	0.039 (3)	0.042 (3)	0.055 (3)	−0.005 (2)	0.005 (2)	0.002 (2)
C28	0.070 (4)	0.064 (3)	0.050 (4)	−0.016 (3)	0.004 (3)	0.005 (3)
C29	0.076 (3)	0.052 (3)	0.067 (3)	−0.005 (2)	0.010 (3)	0.020 (2)
C30	0.060 (3)	0.054 (3)	0.056 (3)	−0.006 (2)	−0.002 (2)	−0.006 (2)
C31	0.046 (3)	0.039 (3)	0.039 (3)	−0.006 (2)	0.011 (3)	−0.002 (2)
C32	0.034 (3)	0.037 (3)	0.042 (4)	−0.002 (2)	0.010 (3)	0.000 (2)
C33	0.043 (3)	0.034 (2)	0.041 (3)	−0.002 (2)	0.010 (2)	−0.003 (2)
C34	0.046 (2)	0.041 (2)	0.047 (3)	−0.0033 (19)	0.012 (2)	0.001 (2)
C35	0.064 (4)	0.059 (3)	0.050 (4)	−0.013 (3)	0.002 (3)	0.006 (3)
C36	0.040 (3)	0.043 (3)	0.050 (3)	−0.003 (2)	0.004 (2)	0.006 (2)
C37	0.037 (2)	0.052 (3)	0.050 (3)	0.002 (2)	0.008 (2)	−0.003 (2)
C38	0.062 (3)	0.049 (3)	0.075 (3)	−0.021 (2)	0.012 (3)	0.000 (2)
C39	0.053 (3)	0.065 (3)	0.057 (3)	−0.004 (2)	0.013 (2)	0.014 (2)
C40	0.046 (3)	0.066 (3)	0.070 (4)	−0.011 (2)	0.000 (2)	0.001 (3)
O1	0.089 (2)	0.0401 (18)	0.084 (3)	−0.0120 (17)	0.0214 (19)	−0.0049 (17)
O2	0.061 (2)	0.063 (2)	0.071 (2)	0.0018 (17)	−0.0037 (17)	0.0143 (18)
O3	0.0558 (19)	0.067 (2)	0.060 (2)	−0.0011 (15)	−0.0072 (16)	0.0114 (16)
O4	0.0389 (18)	0.089 (2)	0.080 (2)	−0.0106 (16)	0.0149 (17)	−0.0050 (19)
O5	0.0523 (19)	0.066 (2)	0.077 (2)	0.0014 (16)	0.0002 (18)	0.0154 (18)
O6	0.0384 (18)	0.092 (2)	0.073 (2)	−0.0116 (17)	0.0114 (16)	−0.0069 (19)
O7	0.085 (2)	0.0436 (18)	0.071 (2)	−0.0106 (17)	0.0194 (17)	−0.0003 (16)
O8	0.0559 (19)	0.0557 (19)	0.066 (2)	−0.0016 (15)	−0.0001 (15)	0.0159 (16)
S1	0.0551 (9)	0.0545 (8)	0.0502 (9)	−0.0083 (6)	0.0100 (7)	0.0104 (6)
S2	0.0500 (8)	0.0611 (8)	0.0471 (9)	−0.0126 (6)	−0.0039 (6)	0.0002 (7)
S3	0.0482 (8)	0.0592 (8)	0.0464 (9)	−0.0120 (6)	−0.0008 (6)	−0.0015 (7)
S4	0.0577 (9)	0.0525 (8)	0.0468 (9)	−0.0106 (7)	0.0074 (7)	0.0097 (7)

C1—C2	1.352 (7)	C21—C22	1.373 (6)
C1—C5	1.480 (7)	C21—C25	1.499 (5)
C1—S1	1.731 (5)	C21—S3	1.710 (4)
C2—C3	1.461 (7)	C22—C23	1.456 (6)
C2—C6	1.491 (7)	C22—C26	1.463 (6)
C3—C4	1.364 (6)	C23—C24	1.355 (7)
C3—C7	1.478 (6)	C23—C27	1.495 (7)
C4—C8	1.519 (5)	C24—C28	1.487 (7)
C4—S1	1.710 (5)	C24—S3	1.721 (5)
C5—H5A	0.9600	C25—H25A	0.9600
C5—H5B	0.9600	C25—H25B	0.9600
C5—H5C	0.9600	C25—H25C	0.9600
C6—O1	1.215 (5)	C26—O5	1.221 (5)
C6—C9	1.504 (6)	C26—C29	1.513 (6)
C7—O2	1.228 (5)	C27—O6	1.211 (5)
C7—C10	1.501 (6)	C27—C30	1.481 (6)
C8—H8A	0.9600	C28—H28A	0.9600
C8—H8B	0.9600	C28—H28B	0.9600
C8—H8C	0.9600	C28—H28C	0.9600
C9—H9A	0.9600	C29—H29A	0.9600
C9—H9B	0.9600	C29—H29B	0.9600
C9—H9C	0.9600	C29—H29C	0.9600
C10—H10A	0.9600	C30—H30A	0.9600
C10—H10B	0.9600	C30—H30B	0.9600
C10—H10C	0.9600	C30—H30C	0.9600
C11—C12	1.374 (6)	C31—C32	1.353 (7)
C11—C15	1.508 (5)	C31—C35	1.514 (7)
C11—S2	1.718 (4)	C31—S4	1.713 (5)
C12—C13	1.441 (6)	C32—C33	1.443 (7)
C12—C16	1.490 (6)	C32—C36	1.502 (7)
C13—C14	1.358 (7)	C33—C34	1.379 (5)
C13—C17	1.505 (7)	C33—C37	1.478 (6)
C14—C18	1.519 (7)	C34—C38	1.492 (5)
C14—S2	1.720 (5)	C34—S4	1.722 (4)
C15—H15A	0.9600	C35—H35A	0.9600
C15—H15B	0.9600	C35—H35B	0.9600
C15—H15C	0.9600	C35—H35C	0.9600
C16—O3	1.221 (5)	C36—O7	1.213 (5)
C16—C19	1.484 (6)	C36—C39	1.477 (7)
C17—O4	1.209 (5)	C37—O8	1.226 (5)
C17—C20	1.489 (6)	C37—C40	1.500 (6)
C18—H18A	0.9600	C38—H38A	0.9600
C18—H18B	0.9600	C38—H38B	0.9600
C18—H18C	0.9600	C38—H38C	0.9600
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600
C2—C1—C5	130.9 (5)	C25—C21—S3	116.3 (3)
C2—C1—S1	110.1 (4)	C21—C22—C23	111.6 (4)
C5—C1—S1	119.0 (4)	C21—C22—C26	127.6 (4)
C1—C2—C3	113.5 (4)	C23—C22—C26	120.4 (4)
C1—C2—C6	120.7 (5)	C24—C23—C22	113.2 (5)
C3—C2—C6	125.7 (5)	C24—C23—C27	120.7 (4)
C4—C3—C2	111.8 (4)	C22—C23—C27	126.1 (5)
C4—C3—C7	127.8 (4)	C23—C24—C28	128.7 (5)
C2—C3—C7	120.1 (4)	C23—C24—S3	110.7 (4)
C3—C4—C8	132.0 (4)	C28—C24—S3	120.5 (4)
C3—C4—S1	111.2 (3)	C21—C25—H25A	109.5
C8—C4—S1	116.8 (3)	C21—C25—H25B	109.5
C1—C5—H5A	109.5	H25A—C25—H25B	109.5
C1—C5—H5B	109.5	C21—C25—H25C	109.5
H5A—C5—H5B	109.5	H25A—C25—H25C	109.5
C1—C5—H5C	109.5	H25B—C25—H25C	109.5
H5A—C5—H5C	109.5	O5—C26—C22	119.5 (4)
H5B—C5—H5C	109.5	O5—C26—C29	120.1 (4)
O1—C6—C2	120.6 (5)	C22—C26—C29	120.3 (4)
O1—C6—C9	120.0 (5)	O6—C27—C30	121.5 (4)
C2—C6—C9	118.9 (4)	O6—C27—C23	120.6 (5)
O2—C7—C3	119.5 (4)	C30—C27—C23	117.5 (4)
O2—C7—C10	120.1 (4)	C24—C28—H28A	109.5
C3—C7—C10	120.4 (4)	C24—C28—H28B	109.5
C4—C8—H8A	109.5	H28A—C28—H28B	109.5
C4—C8—H8B	109.5	C24—C28—H28C	109.5
H8A—C8—H8B	109.5	H28A—C28—H28C	109.5
C4—C8—H8C	109.5	H28B—C28—H28C	109.5
H8A—C8—H8C	109.5	C26—C29—H29A	109.5
H8B—C8—H8C	109.5	C26—C29—H29B	109.5
C6—C9—H9A	109.5	H29A—C29—H29B	109.5
C6—C9—H9B	109.5	C26—C29—H29C	109.5
H9A—C9—H9B	109.5	H29A—C29—H29C	109.5
C6—C9—H9C	109.5	H29B—C29—H29C	109.5
H9A—C9—H9C	109.5	C27—C30—H30A	109.5
H9B—C9—H9C	109.5	C27—C30—H30B	109.5
C7—C10—H10A	109.5	H30A—C30—H30B	109.5
C7—C10—H10B	109.5	C27—C30—H30C	109.5
H10A—C10—H10B	109.5	H30A—C30—H30C	109.5
C7—C10—H10C	109.5	H30B—C30—H30C	109.5
H10A—C10—H10C	109.5	C32—C31—C35	128.0 (5)
H10B—C10—H10C	109.5	C32—C31—S4	111.1 (4)
C12—C11—C15	131.9 (4)	C35—C31—S4	120.8 (4)
C12—C11—S2	110.3 (3)	C31—C32—C33	112.9 (4)
C15—C11—S2	117.6 (3)	C31—C32—C36	120.7 (5)
C11—C12—C13	112.0 (4)	C33—C32—C36	126.4 (5)
C11—C12—C16	126.4 (4)	C34—C33—C32	112.6 (4)
C13—C12—C16	121.3 (4)	C34—C33—C37	126.2 (4)
C14—C13—C12	114.1 (5)	C32—C33—C37	120.8 (4)
C14—C13—C17	120.3 (4)	C33—C34—C38	133.6 (4)
C12—C13—C17	125.5 (5)	C33—C34—S4	109.9 (3)
C13—C14—C18	130.4 (5)	C38—C34—S4	116.4 (3)
C13—C14—S2	109.8 (4)	C31—C35—H35A	109.5
C18—C14—S2	119.8 (4)	C31—C35—H35B	109.5
C11—C15—H15A	109.5	H35A—C35—H35B	109.5
C11—C15—H15B	109.5	C31—C35—H35C	109.5
H15A—C15—H15B	109.5	H35A—C35—H35C	109.5
C11—C15—H15C	109.5	H35B—C35—H35C	109.5
H15A—C15—H15C	109.5	O7—C36—C39	122.2 (4)
H15B—C15—H15C	109.5	O7—C36—C32	119.5 (5)
O3—C16—C19	120.6 (4)	C39—C36—C32	117.9 (4)
O3—C16—C12	118.3 (4)	O8—C37—C33	118.3 (4)
C19—C16—C12	121.2 (4)	O8—C37—C40	120.5 (4)
O4—C17—C20	121.6 (4)	C33—C37—C40	121.2 (4)
O4—C17—C13	119.5 (5)	C34—C38—H38A	109.5
C20—C17—C13	118.5 (4)	C34—C38—H38B	109.5
C14—C18—H18A	109.5	H38A—C38—H38B	109.5
C14—C18—H18B	109.5	C34—C38—H38C	109.5
H18A—C18—H18B	109.5	H38A—C38—H38C	109.5
C14—C18—H18C	109.5	H38B—C38—H38C	109.5
H18A—C18—H18C	109.5	C36—C39—H39A	109.5
H18B—C18—H18C	109.5	C36—C39—H39B	109.5
C16—C19—H19A	109.5	H39A—C39—H39B	109.5
C16—C19—H19B	109.5	C36—C39—H39C	109.5
H19A—C19—H19B	109.5	H39A—C39—H39C	109.5
C16—C19—H19C	109.5	H39B—C39—H39C	109.5
H19A—C19—H19C	109.5	C37—C40—H40A	109.5
H19B—C19—H19C	109.5	C37—C40—H40B	109.5
C17—C20—H20A	109.5	H40A—C40—H40B	109.5
C17—C20—H20B	109.5	C37—C40—H40C	109.5
H20A—C20—H20B	109.5	H40A—C40—H40C	109.5
C17—C20—H20C	109.5	H40B—C40—H40C	109.5
H20A—C20—H20C	109.5	C4—S1—C1	93.5 (2)
H20B—C20—H20C	109.5	C11—S2—C14	93.8 (2)
C22—C21—C25	132.4 (4)	C21—S3—C24	93.3 (2)
C22—C21—S3	111.2 (3)	C31—S4—C34	93.4 (2)
C5—C1—C2—C3	179.5 (5)	C22—C23—C24—C28	178.8 (5)
S1—C1—C2—C3	0.0 (5)	C27—C23—C24—C28	1.3 (8)
C5—C1—C2—C6	3.7 (9)	C22—C23—C24—S3	2.1 (5)
S1—C1—C2—C6	−175.8 (4)	C27—C23—C24—S3	−175.4 (4)
C1—C2—C3—C4	−0.3 (6)	C21—C22—C26—O5	164.3 (4)
C6—C2—C3—C4	175.2 (4)	C23—C22—C26—O5	−7.8 (6)
C1—C2—C3—C7	174.2 (4)	C21—C22—C26—C29	−15.6 (7)
C6—C2—C3—C7	−10.2 (7)	C23—C22—C26—C29	172.2 (4)
C2—C3—C4—C8	177.8 (4)	C24—C23—C27—O6	−59.7 (7)
C7—C3—C4—C8	3.8 (8)	C22—C23—C27—O6	123.1 (5)
C2—C3—C4—S1	0.4 (5)	C24—C23—C27—C30	113.2 (5)
C7—C3—C4—S1	−173.6 (4)	C22—C23—C27—C30	−64.0 (6)
C1—C2—C6—O1	−61.2 (7)	C35—C31—C32—C33	−179.4 (5)
C3—C2—C6—O1	123.5 (5)	S4—C31—C32—C33	−2.1 (5)
C1—C2—C6—C9	111.0 (5)	C35—C31—C32—C36	−1.3 (8)
C3—C2—C6—C9	−64.2 (6)	S4—C31—C32—C36	176.1 (4)
C4—C3—C7—O2	165.7 (4)	C31—C32—C33—C34	1.5 (6)
C2—C3—C7—O2	−7.9 (7)	C36—C32—C33—C34	−176.6 (4)
C4—C3—C7—C10	−14.1 (7)	C31—C32—C33—C37	−172.0 (4)
C2—C3—C7—C10	172.3 (4)	C36—C32—C33—C37	9.9 (7)
C15—C11—C12—C13	−176.3 (4)	C32—C33—C34—C38	−177.1 (4)
S2—C11—C12—C13	−1.2 (5)	C37—C33—C34—C38	−4.0 (7)
C15—C11—C12—C16	−1.7 (8)	C32—C33—C34—S4	−0.2 (5)
S2—C11—C12—C16	173.4 (4)	C37—C33—C34—S4	172.9 (4)
C11—C12—C13—C14	0.9 (6)	C31—C32—C36—O7	59.9 (6)
C16—C12—C13—C14	−174.0 (4)	C33—C32—C36—O7	−122.2 (5)
C11—C12—C13—C17	−174.9 (4)	C31—C32—C36—C39	−113.3 (5)
C16—C12—C13—C17	10.1 (7)	C33—C32—C36—C39	64.6 (6)
C12—C13—C14—C18	179.7 (5)	C34—C33—C37—O8	−163.6 (4)
C17—C13—C14—C18	−4.2 (8)	C32—C33—C37—O8	8.9 (6)
C12—C13—C14—S2	−0.2 (6)	C34—C33—C37—C40	16.5 (7)
C17—C13—C14—S2	175.9 (4)	C32—C33—C37—C40	−170.9 (4)
C11—C12—C16—O3	−164.6 (4)	C3—C4—S1—C1	−0.4 (4)
C13—C12—C16—O3	9.5 (6)	C8—C4—S1—C1	−178.2 (3)
C11—C12—C16—C19	15.6 (7)	C2—C1—S1—C4	0.2 (4)
C13—C12—C16—C19	−170.2 (4)	C5—C1—S1—C4	−179.4 (4)
C14—C13—C17—O4	61.3 (7)	C12—C11—S2—C14	1.0 (3)
C12—C13—C17—O4	−123.0 (5)	C15—C11—S2—C14	176.8 (3)
C14—C13—C17—C20	−111.7 (5)	C13—C14—S2—C11	−0.4 (4)
C12—C13—C17—C20	63.9 (6)	C18—C14—S2—C11	179.7 (4)
C25—C21—C22—C23	177.8 (4)	C22—C21—S3—C24	1.4 (4)
S3—C21—C22—C23	−0.5 (5)	C25—C21—S3—C24	−177.1 (3)
C25—C21—C22—C26	5.0 (8)	C23—C24—S3—C21	−2.0 (4)
S3—C21—C22—C26	−173.2 (4)	C28—C24—S3—C21	−179.1 (4)
C21—C22—C23—C24	−1.1 (6)	C32—C31—S4—C34	1.7 (4)
C26—C22—C23—C24	172.2 (4)	C35—C31—S4—C34	179.3 (4)
C21—C22—C23—C27	176.3 (4)	C33—C34—S4—C31	−0.9 (3)
C26—C22—C23—C27	−10.4 (7)	C38—C34—S4—C31	176.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30B···O5	0.96	2.48	2.978 (4)	112
C35—H35C···O6i	0.96	2.44	3.276 (6)	145
C39—H39A···O6i	0.96	2.56	3.435 (6)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C35—H35C⋯O6i	0.96	2.44	3.276 (6)	145
C39—H39A⋯O6i	0.96	2.56	3.435 (6)	152

Symmetry code: (i) .