Diethyl 3,4-bis-(2,5-dimethoxy-benz-yl)thieno[2,3-b]thio-phene-2,5-di-car-boxylate.

In the title compound, C(30)H(32)O(8)S(2), the dihedral angle between the two benzene rings is 18.8 (1)°. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O hydrogen bonds. In the crystal structure, the mol-ecules are linked via weak inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions between two benzene rings [centroid-centroid distance = 3.672 (1) Å].

Related literature

For the biological activity of thio­phene derivatives, see: Tapia et al. (2003 ▶); Dallemagne et al. (2003 ▶). For related structures, see: Dufresne & Skene (2008 ▶); Gunasekaran et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶)

Experimental

Crystal data

C30H32O8S2

M = 584.68

Triclinic,

a = 9.9439 (3) Å

b = 10.8163 (3) Å

c = 14.7536 (5) Å

α = 82.610 (2)°

β = 89.490 (2)°

γ = 64.983 (1)°

V = 1424.20 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 295 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.959

40341 measured reflections

11207 independent reflections

7512 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.02

11207 reflections

367 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.21 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042214/bt5095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042214/bt5095Isup2.hkl

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

C30H32O8S2	Z = 2
Mr = 584.68	F(000) = 616
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9439 (3) Å	Cell parameters from 7622 reflections
b = 10.8163 (3) Å	θ = 2.3–32.6°
c = 14.7536 (5) Å	µ = 0.24 mm−1
α = 82.610 (2)°	T = 295 K
β = 89.490 (2)°	Block, colourless
γ = 64.983 (1)°	0.24 × 0.20 × 0.18 mm
V = 1424.20 (8) Å3

Bruker Kappa APEX2 CCD diffractometer	11207 independent reflections
Radiation source: fine-focus sealed tube	7512 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 33.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→13
Tmin = 0.945, Tmax = 0.959	k = −16→16
40341 measured reflections	l = −22→22

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.2259P] where P = (Fo2 + 2Fc2)/3
11207 reflections	(Δ/σ)max < 0.001
367 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.33884 (12)	0.45771 (12)	0.29435 (9)	0.0319 (2)
C2	0.45021 (11)	0.29918 (12)	0.43341 (9)	0.0311 (2)
C3	0.50197 (11)	0.23469 (11)	0.35827 (8)	0.0279 (2)
C4	0.43974 (11)	0.32916 (11)	0.27586 (8)	0.0279 (2)
C5	0.45557 (11)	0.32473 (11)	0.17974 (8)	0.0281 (2)
C6	0.36170 (13)	0.44795 (12)	0.13047 (9)	0.0325 (2)
C7	0.48843 (12)	0.24180 (13)	0.53018 (9)	0.0352 (3)
C8	0.4489 (2)	0.30018 (16)	0.68064 (10)	0.0521 (4)
H8A	0.5547	0.2632	0.6956	0.062*
H8B	0.4148	0.2303	0.7021	0.062*
C9	0.3674 (2)	0.42647 (18)	0.72430 (12)	0.0566 (4)
H9A	0.3969	0.4971	0.6991	0.085*
H9B	0.3904	0.4057	0.7891	0.085*
H9C	0.2625	0.4580	0.7128	0.085*
C10	0.33664 (14)	0.48317 (12)	0.03113 (9)	0.0363 (3)
C11	0.17568 (19)	0.64930 (15)	−0.08706 (10)	0.0504 (4)
H11A	0.2622	0.6182	−0.1238	0.060*
H11B	0.1266	0.7491	−0.0991	0.060*
C12	0.07259 (19)	0.5918 (2)	−0.11375 (13)	0.0612 (4)
H12A	0.1226	0.4930	−0.1047	0.092*
H12B	0.0408	0.6239	−0.1770	0.092*
H12C	−0.0124	0.6213	−0.0768	0.092*
C13	0.60622 (11)	0.08518 (11)	0.36206 (9)	0.0307 (2)
H13A	0.5851	0.0515	0.3086	0.037*
H13B	0.5867	0.0342	0.4156	0.037*
C14	0.76908 (11)	0.05525 (12)	0.36583 (8)	0.0309 (2)
C15	0.81823 (12)	0.15692 (13)	0.35845 (10)	0.0371 (3)
H15	0.7493	0.2487	0.3492	0.045*
C16	0.96928 (13)	0.12566 (15)	0.36447 (10)	0.0424 (3)
C17	1.07178 (14)	−0.00949 (16)	0.37866 (12)	0.0522 (4)
H17	1.1727	−0.0313	0.3835	0.063*
C18	1.02365 (14)	−0.11288 (15)	0.38571 (12)	0.0520 (4)
H18	1.0930	−0.2045	0.3950	0.062*
C19	0.87411 (13)	−0.08212 (13)	0.37913 (10)	0.0389 (3)
C20	1.15560 (18)	0.2084 (2)	0.36269 (15)	0.0663 (5)
H20A	1.1985	0.1574	0.4214	0.099*
H20B	1.1659	0.2933	0.3551	0.099*
H20C	1.2059	0.1550	0.3154	0.099*
C21	0.92037 (18)	−0.31882 (15)	0.40392 (16)	0.0665 (5)
H21A	0.9815	−0.3431	0.3525	0.100*
H21B	0.8675	−0.3755	0.4136	0.100*
H21C	0.9818	−0.3329	0.4576	0.100*
C22	0.56168 (12)	0.20106 (11)	0.13954 (9)	0.0306 (2)
H22A	0.6533	0.1583	0.1773	0.037*
H22B	0.5850	0.2314	0.0791	0.037*
C23	0.50319 (12)	0.09487 (11)	0.13174 (8)	0.0284 (2)
C24	0.60272 (12)	−0.03646 (11)	0.11506 (8)	0.0303 (2)
C25	0.55198 (14)	−0.13381 (12)	0.10341 (9)	0.0347 (3)
H25	0.6187	−0.2204	0.0913	0.042*
C26	0.40264 (14)	−0.10439 (13)	0.10943 (9)	0.0365 (3)
H26	0.3693	−0.1709	0.1016	0.044*
C27	0.30409 (13)	0.02372 (13)	0.12702 (10)	0.0368 (3)
C28	0.35525 (13)	0.12273 (12)	0.13736 (9)	0.0341 (3)
H28	0.2879	0.2098	0.1483	0.041*
C29	0.85392 (16)	−0.19303 (15)	0.10302 (15)	0.0629 (5)
H29A	0.8512	−0.2543	0.1555	0.094*
H29B	0.9515	−0.1954	0.1000	0.094*
H29C	0.8306	−0.2214	0.0485	0.094*
C30	0.09936 (18)	−0.03504 (18)	0.13132 (16)	0.0695 (6)
H30A	0.1141	−0.0652	0.0721	0.104*
H30B	−0.0048	0.0039	0.1422	0.104*
H30C	0.1515	−0.1122	0.1774	0.104*
O1	0.41917 (11)	0.34007 (10)	0.58310 (7)	0.0441 (2)
O2	0.57034 (11)	0.12509 (10)	0.55927 (7)	0.0472 (2)
O3	0.22256 (12)	0.60698 (10)	0.00899 (7)	0.0478 (2)
O4	0.40665 (12)	0.41188 (10)	−0.02441 (7)	0.0465 (2)
O5	1.00283 (11)	0.23685 (12)	0.35686 (9)	0.0599 (3)
O6	0.81740 (10)	−0.17839 (10)	0.38624 (9)	0.0527 (3)
O7	0.74872 (9)	−0.05753 (9)	0.11046 (7)	0.0422 (2)
O8	0.15417 (11)	0.06544 (10)	0.13456 (9)	0.0567 (3)
S1	0.25637 (3)	0.57151 (3)	0.19869 (2)	0.03757 (9)
S2	0.32384 (3)	0.47150 (3)	0.40793 (2)	0.03599 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0286 (5)	0.0222 (5)	0.0380 (6)	−0.0045 (4)	−0.0017 (4)	−0.0035 (5)
C2	0.0230 (4)	0.0262 (5)	0.0381 (6)	−0.0055 (4)	−0.0013 (4)	−0.0014 (5)
C3	0.0186 (4)	0.0217 (5)	0.0395 (6)	−0.0059 (4)	−0.0011 (4)	−0.0009 (4)
C4	0.0219 (4)	0.0202 (5)	0.0391 (6)	−0.0061 (4)	−0.0003 (4)	−0.0049 (4)
C5	0.0260 (5)	0.0193 (5)	0.0389 (6)	−0.0090 (4)	0.0005 (4)	−0.0058 (4)
C6	0.0346 (5)	0.0215 (5)	0.0380 (6)	−0.0082 (4)	−0.0005 (5)	−0.0058 (5)
C7	0.0258 (5)	0.0351 (6)	0.0410 (7)	−0.0103 (4)	−0.0003 (4)	−0.0022 (5)
C8	0.0692 (10)	0.0439 (8)	0.0348 (7)	−0.0176 (7)	−0.0034 (7)	0.0002 (6)
C9	0.0710 (10)	0.0516 (9)	0.0457 (9)	−0.0236 (8)	0.0054 (7)	−0.0103 (7)
C10	0.0423 (6)	0.0236 (5)	0.0406 (7)	−0.0119 (5)	−0.0031 (5)	−0.0032 (5)
C11	0.0619 (9)	0.0350 (7)	0.0397 (8)	−0.0092 (6)	−0.0058 (6)	0.0049 (6)
C12	0.0542 (9)	0.0628 (11)	0.0544 (10)	−0.0139 (8)	−0.0071 (7)	−0.0045 (8)
C13	0.0217 (4)	0.0215 (5)	0.0438 (7)	−0.0053 (4)	−0.0014 (4)	−0.0009 (5)
C14	0.0207 (4)	0.0281 (5)	0.0375 (6)	−0.0051 (4)	−0.0006 (4)	−0.0011 (5)
C15	0.0253 (5)	0.0309 (6)	0.0500 (8)	−0.0089 (4)	−0.0035 (5)	0.0016 (5)
C16	0.0282 (5)	0.0422 (7)	0.0562 (9)	−0.0161 (5)	−0.0016 (5)	0.0002 (6)
C17	0.0221 (5)	0.0527 (9)	0.0744 (11)	−0.0104 (5)	−0.0014 (6)	−0.0026 (8)
C18	0.0233 (5)	0.0375 (7)	0.0813 (11)	−0.0014 (5)	−0.0018 (6)	−0.0013 (7)
C19	0.0250 (5)	0.0287 (6)	0.0546 (8)	−0.0041 (4)	−0.0006 (5)	−0.0021 (6)
C20	0.0417 (8)	0.0801 (13)	0.0891 (14)	−0.0394 (9)	0.0021 (8)	−0.0048 (10)
C21	0.0420 (8)	0.0258 (7)	0.1165 (17)	−0.0014 (6)	0.0003 (9)	−0.0035 (8)
C22	0.0275 (5)	0.0214 (5)	0.0413 (7)	−0.0080 (4)	0.0039 (4)	−0.0080 (5)
C23	0.0305 (5)	0.0195 (5)	0.0325 (6)	−0.0079 (4)	−0.0004 (4)	−0.0040 (4)
C24	0.0312 (5)	0.0224 (5)	0.0333 (6)	−0.0074 (4)	−0.0010 (4)	−0.0040 (4)
C25	0.0398 (6)	0.0213 (5)	0.0392 (7)	−0.0086 (4)	−0.0008 (5)	−0.0066 (5)
C26	0.0436 (6)	0.0259 (6)	0.0423 (7)	−0.0169 (5)	−0.0042 (5)	−0.0041 (5)
C27	0.0325 (5)	0.0290 (6)	0.0489 (8)	−0.0136 (5)	−0.0018 (5)	−0.0029 (5)
C28	0.0318 (5)	0.0234 (5)	0.0454 (7)	−0.0095 (4)	0.0026 (5)	−0.0070 (5)
C29	0.0359 (7)	0.0305 (7)	0.1111 (16)	−0.0009 (6)	0.0019 (8)	−0.0191 (8)
C30	0.0446 (8)	0.0443 (9)	0.1278 (18)	−0.0277 (7)	−0.0021 (9)	−0.0076 (10)
O1	0.0496 (5)	0.0361 (5)	0.0352 (5)	−0.0082 (4)	−0.0011 (4)	−0.0010 (4)
O2	0.0403 (5)	0.0374 (5)	0.0461 (6)	−0.0019 (4)	−0.0060 (4)	0.0038 (4)
O3	0.0566 (6)	0.0305 (5)	0.0384 (5)	−0.0021 (4)	−0.0070 (4)	−0.0016 (4)
O4	0.0572 (6)	0.0320 (5)	0.0414 (5)	−0.0092 (4)	0.0003 (4)	−0.0094 (4)
O5	0.0373 (5)	0.0541 (7)	0.0934 (9)	−0.0274 (5)	−0.0039 (5)	0.0010 (6)
O6	0.0291 (4)	0.0249 (4)	0.0941 (9)	−0.0031 (3)	−0.0010 (5)	−0.0033 (5)
O7	0.0295 (4)	0.0246 (4)	0.0677 (7)	−0.0052 (3)	0.0021 (4)	−0.0119 (4)
O8	0.0339 (5)	0.0339 (5)	0.1055 (10)	−0.0176 (4)	0.0040 (5)	−0.0095 (6)
S1	0.03985 (16)	0.02006 (14)	0.03953 (18)	0.00000 (11)	−0.00335 (12)	−0.00368 (12)
S2	0.03251 (14)	0.02638 (15)	0.03817 (17)	−0.00160 (11)	0.00029 (11)	−0.00594 (12)

C1—C4	1.3882 (15)	C16—O5	1.3691 (17)
C1—S2	1.7010 (13)	C16—C17	1.373 (2)
C1—S1	1.7028 (12)	C17—C18	1.383 (2)
C2—C3	1.3658 (17)	C17—H17	0.9300
C2—C7	1.4664 (18)	C18—C19	1.3810 (17)
C2—S2	1.7440 (11)	C18—H18	0.9300
C3—C4	1.4367 (16)	C19—O6	1.3713 (16)
C3—C13	1.5009 (15)	C20—O5	1.4175 (17)
C4—C5	1.4302 (17)	C20—H20A	0.9600
C5—C6	1.3736 (16)	C20—H20B	0.9600
C5—C22	1.5011 (15)	C20—H20C	0.9600
C6—C10	1.4622 (18)	C21—O6	1.4182 (16)
C6—S1	1.7434 (12)	C21—H21A	0.9600
C7—O2	1.1993 (15)	C21—H21B	0.9600
C7—O1	1.3411 (16)	C21—H21C	0.9600
C8—O1	1.4438 (17)	C22—C23	1.5070 (15)
C8—C9	1.489 (2)	C22—H22A	0.9700
C8—H8A	0.9700	C22—H22B	0.9700
C8—H8B	0.9700	C23—C28	1.3753 (16)
C9—H9A	0.9600	C23—C24	1.3980 (15)
C9—H9B	0.9600	C24—O7	1.3735 (14)
C9—H9C	0.9600	C24—C25	1.3749 (17)
C10—O4	1.2038 (16)	C25—C26	1.3856 (18)
C10—O3	1.3402 (15)	C25—H25	0.9300
C11—O3	1.4489 (17)	C26—C27	1.3738 (18)
C11—C12	1.484 (3)	C26—H26	0.9300
C11—H11A	0.9700	C27—O8	1.3709 (15)
C11—H11B	0.9700	C27—C28	1.3904 (17)
C12—H12A	0.9600	C28—H28	0.9300
C12—H12B	0.9600	C29—O7	1.4132 (16)
C12—H12C	0.9600	C29—H29A	0.9600
C13—C14	1.5113 (14)	C29—H29B	0.9600
C13—H13A	0.9700	C29—H29C	0.9600
C13—H13B	0.9700	C30—O8	1.4126 (18)
C14—C15	1.3723 (17)	C30—H30A	0.9600
C14—C19	1.3976 (16)	C30—H30B	0.9600
C15—C16	1.3940 (16)	C30—H30C	0.9600
C15—H15	0.9300
C4—C1—S2	113.79 (9)	C16—C17—H17	120.3
C4—C1—S1	113.60 (10)	C18—C17—H17	120.3
S2—C1—S1	132.60 (7)	C19—C18—C17	120.97 (13)
C3—C2—C7	128.19 (11)	C19—C18—H18	119.5
C3—C2—S2	114.17 (9)	C17—C18—H18	119.5
C7—C2—S2	117.65 (9)	O6—C19—C18	124.55 (12)
C2—C3—C4	110.44 (10)	O6—C19—C14	115.56 (10)
C2—C3—C13	124.37 (11)	C18—C19—C14	119.89 (12)
C4—C3—C13	125.17 (11)	O5—C20—H20A	109.5
C1—C4—C5	111.91 (10)	O5—C20—H20B	109.5
C1—C4—C3	111.79 (11)	H20A—C20—H20B	109.5
C5—C4—C3	136.30 (10)	O5—C20—H20C	109.5
C6—C5—C4	110.87 (10)	H20A—C20—H20C	109.5
C6—C5—C22	125.33 (11)	H20B—C20—H20C	109.5
C4—C5—C22	123.80 (10)	O6—C21—H21A	109.5
C5—C6—C10	128.19 (11)	O6—C21—H21B	109.5
C5—C6—S1	113.52 (10)	H21A—C21—H21B	109.5
C10—C6—S1	118.23 (9)	O6—C21—H21C	109.5
O2—C7—O1	123.98 (13)	H21A—C21—H21C	109.5
O2—C7—C2	126.05 (13)	H21B—C21—H21C	109.5
O1—C7—C2	109.97 (10)	C5—C22—C23	113.91 (9)
O1—C8—C9	106.89 (12)	C5—C22—H22A	108.8
O1—C8—H8A	110.3	C23—C22—H22A	108.8
C9—C8—H8A	110.3	C5—C22—H22B	108.8
O1—C8—H8B	110.3	C23—C22—H22B	108.8
C9—C8—H8B	110.3	H22A—C22—H22B	107.7
H8A—C8—H8B	108.6	C28—C23—C24	118.43 (10)
C8—C9—H9A	109.5	C28—C23—C22	122.87 (10)
C8—C9—H9B	109.5	C24—C23—C22	118.67 (10)
H9A—C9—H9B	109.5	O7—C24—C25	124.38 (10)
C8—C9—H9C	109.5	O7—C24—C23	115.46 (10)
H9A—C9—H9C	109.5	C25—C24—C23	120.15 (10)
H9B—C9—H9C	109.5	C24—C25—C26	120.79 (11)
O4—C10—O3	123.61 (13)	C24—C25—H25	119.6
O4—C10—C6	125.62 (12)	C26—C25—H25	119.6
O3—C10—C6	110.77 (11)	C27—C26—C25	119.58 (11)
O3—C11—C12	111.27 (13)	C27—C26—H26	120.2
O3—C11—H11A	109.4	C25—C26—H26	120.2
C12—C11—H11A	109.4	O8—C27—C26	125.18 (11)
O3—C11—H11B	109.4	O8—C27—C28	115.27 (11)
C12—C11—H11B	109.4	C26—C27—C28	119.55 (11)
H11A—C11—H11B	108.0	C23—C28—C27	121.49 (11)
C11—C12—H12A	109.5	C23—C28—H28	119.3
C11—C12—H12B	109.5	C27—C28—H28	119.3
H12A—C12—H12B	109.5	O7—C29—H29A	109.5
C11—C12—H12C	109.5	O7—C29—H29B	109.5
H12A—C12—H12C	109.5	H29A—C29—H29B	109.5
H12B—C12—H12C	109.5	O7—C29—H29C	109.5
C3—C13—C14	114.58 (9)	H29A—C29—H29C	109.5
C3—C13—H13A	108.6	H29B—C29—H29C	109.5
C14—C13—H13A	108.6	O8—C30—H30A	109.5
C3—C13—H13B	108.6	O8—C30—H30B	109.5
C14—C13—H13B	108.6	H30A—C30—H30B	109.5
H13A—C13—H13B	107.6	O8—C30—H30C	109.5
C15—C14—C19	118.60 (10)	H30A—C30—H30C	109.5
C15—C14—C13	122.91 (10)	H30B—C30—H30C	109.5
C19—C14—C13	118.49 (10)	C7—O1—C8	116.59 (11)
C14—C15—C16	121.43 (12)	C10—O3—C11	116.74 (11)
C14—C15—H15	119.3	C16—O5—C20	116.70 (13)
C16—C15—H15	119.3	C19—O6—C21	117.14 (11)
O5—C16—C17	124.94 (12)	C24—O7—C29	116.74 (11)
O5—C16—C15	115.38 (12)	C27—O8—C30	117.02 (12)
C17—C16—C15	119.67 (13)	C1—S1—C6	90.05 (6)
C16—C17—C18	119.44 (12)	C1—S2—C2	89.71 (6)
C7—C2—C3—C4	−178.22 (11)	C13—C14—C19—O6	0.95 (18)
S2—C2—C3—C4	1.40 (12)	C15—C14—C19—C18	0.8 (2)
C7—C2—C3—C13	3.19 (18)	C13—C14—C19—C18	−178.01 (14)
S2—C2—C3—C13	−177.18 (8)	C6—C5—C22—C23	−97.49 (14)
S2—C1—C4—C5	−176.41 (8)	C4—C5—C22—C23	82.76 (13)
S1—C1—C4—C5	2.66 (13)	C5—C22—C23—C28	16.39 (17)
S2—C1—C4—C3	3.39 (13)	C5—C22—C23—C24	−165.78 (11)
S1—C1—C4—C3	−177.54 (8)	C28—C23—C24—O7	−179.86 (11)
C2—C3—C4—C1	−3.00 (13)	C22—C23—C24—O7	2.21 (16)
C13—C3—C4—C1	175.58 (10)	C28—C23—C24—C25	0.90 (18)
C2—C3—C4—C5	176.74 (12)	C22—C23—C24—C25	−177.03 (11)
C13—C3—C4—C5	−4.7 (2)	O7—C24—C25—C26	179.78 (12)
C1—C4—C5—C6	−2.46 (14)	C23—C24—C25—C26	−1.05 (19)
C3—C4—C5—C6	177.81 (12)	C24—C25—C26—C27	0.2 (2)
C1—C4—C5—C22	177.32 (10)	C25—C26—C27—O8	179.97 (13)
C3—C4—C5—C22	−2.4 (2)	C25—C26—C27—C28	0.8 (2)
C4—C5—C6—C10	−175.76 (12)	C24—C23—C28—C27	0.12 (19)
C22—C5—C6—C10	4.5 (2)	C22—C23—C28—C27	177.95 (12)
C4—C5—C6—S1	1.26 (13)	O8—C27—C28—C23	179.79 (12)
C22—C5—C6—S1	−178.52 (9)	C26—C27—C28—C23	−1.0 (2)
C3—C2—C7—O2	−2.2 (2)	O2—C7—O1—C8	0.9 (2)
S2—C2—C7—O2	178.21 (11)	C2—C7—O1—C8	−178.40 (11)
C3—C2—C7—O1	177.11 (11)	C9—C8—O1—C7	176.97 (12)
S2—C2—C7—O1	−2.51 (14)	O4—C10—O3—C11	5.4 (2)
C5—C6—C10—O4	−7.8 (2)	C6—C10—O3—C11	−174.08 (12)
S1—C6—C10—O4	175.33 (11)	C12—C11—O3—C10	83.66 (17)
C5—C6—C10—O3	171.65 (12)	C17—C16—O5—C20	1.1 (2)
S1—C6—C10—O3	−5.24 (15)	C15—C16—O5—C20	−179.98 (15)
C2—C3—C13—C14	−89.64 (14)	C18—C19—O6—C21	1.7 (2)
C4—C3—C13—C14	91.98 (13)	C14—C19—O6—C21	−177.22 (15)
C3—C13—C14—C15	−5.37 (18)	C25—C24—O7—C29	−7.0 (2)
C3—C13—C14—C19	173.40 (12)	C23—C24—O7—C29	173.75 (14)
C19—C14—C15—C16	−0.4 (2)	C26—C27—O8—C30	5.4 (2)
C13—C14—C15—C16	178.40 (13)	C28—C27—O8—C30	−175.40 (15)
C14—C15—C16—O5	−179.37 (13)	C4—C1—S1—C6	−1.63 (10)
C14—C15—C16—C17	−0.4 (2)	S2—C1—S1—C6	177.21 (10)
O5—C16—C17—C18	179.61 (16)	C5—C6—S1—C1	0.17 (10)
C15—C16—C17—C18	0.8 (3)	C10—C6—S1—C1	177.51 (10)
C16—C17—C18—C19	−0.3 (3)	C4—C1—S2—C2	−2.18 (9)
C17—C18—C19—O6	−179.35 (16)	S1—C1—S2—C2	178.98 (10)
C17—C18—C19—C14	−0.5 (3)	C3—C2—S2—C1	0.39 (9)
C15—C14—C19—O6	179.78 (13)	C7—C2—S2—C1	−179.94 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2	0.97	2.43	2.9923 (17)	117
C22—H22B···O4	0.97	2.38	3.0169 (16)	123
C17—H17···O2i	0.93	2.43	3.3267 (16)	162
C25—H25···O4ii	0.93	2.51	3.2280 (16)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O2	0.97	2.43	2.9923 (17)	117
C22—H22B⋯O4	0.97	2.38	3.0169 (16)	123
C17—H17⋯O2i	0.93	2.43	3.3267 (16)	162
C25—H25⋯O4ii	0.93	2.51	3.2280 (16)	134

Symmetry codes: (i) ; (ii) .