5-Fluoro-2-methyl-3-phenyl-sulfonyl-1-benzofuran.

There are two symmetry-independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(15)H(11)FO(3)S. The crystal studied was an inversion twin with a 0.21 (12):0.79 (12) domain ratio. In the crystal structure, the two independent mol-ecules are related by a pseudo-inversion center. The dihedral angles formed by the phenyl ring and the plane of the benzofuran fragment are 80.2 (1)° in mol-ecule A and 80.7 (1)° in mol-ecule B. In the crystal structure, the A and B mol-ecules are linked by aromatic π-π inter-actions between the furan and benzene rings of neighbouring benzofuran systems; the centroid-centroid distances are 3.671 (7) and 3.715 (7) Å. In addition, the crystal structure also exhibits two weak non-classical inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar 5-halo-2-methyl-3-phenyl­sulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ▶,b ▶,c ▶). For natural products with benzofuran ring systems, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶).

Experimental

Crystal data

C15H11FO3S

M = 290.30

Monoclinic,

a = 7.377 (2) Å

b = 19.831 (4) Å

c = 9.025 (2) Å

β = 101.367 (3)°

V = 1294.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 173 K

0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.930, T max = 0.990

6055 measured reflections

3996 independent reflections

3154 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.115

S = 1.07

3996 reflections

362 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1642 Friedel pairs

Flack parameter: 0.21 (12)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055068/ng2699sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055068/ng2699Isup2.hkl

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

C15H11FO3S	F(000) = 600
Mr = 290.30	Dx = 1.490 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2yb	Cell parameters from 2528 reflections
a = 7.377 (2) Å	θ = 2.3–25.7°
b = 19.831 (4) Å	µ = 0.27 mm−1
c = 9.025 (2) Å	T = 173 K
β = 101.367 (3)°	Block, colourless
V = 1294.4 (5) Å3	0.40 × 0.20 × 0.05 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3996 independent reflections
Radiation source: Rotating Anode	3154 reflections with I > 2σ(I)
HELIOS	Rint = 0.062
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −19→23
Tmin = 0.930, Tmax = 0.990	l = −10→10
6055 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.9464P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3996 reflections	Δρmax = 0.26 e Å−3
362 parameters	Δρmin = −0.35 e Å−3
1 restraint	Absolute structure: Flack (1983), 1642 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.21 (12)

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
S1	0.40869 (16)	0.34079 (7)	0.07406 (13)	0.0315 (3)
S2	0.29228 (16)	0.56069 (6)	0.66799 (14)	0.0314 (3)
O1	0.6428 (5)	0.40440 (18)	0.4794 (4)	0.0356 (9)
O2	0.2917 (5)	0.38775 (19)	−0.0206 (4)	0.0366 (10)
O3	0.3351 (5)	0.27849 (19)	0.1139 (4)	0.0419 (10)
O4	0.0634 (5)	0.5048 (2)	0.2569 (4)	0.0380 (10)
O5	0.3689 (5)	0.62390 (18)	0.6366 (4)	0.0396 (9)
O6	0.4061 (5)	0.51239 (18)	0.7608 (4)	0.0370 (9)
F1	0.5315 (5)	0.62712 (18)	0.1306 (4)	0.0595 (10)
F2	0.1460 (5)	0.27594 (17)	0.5845 (4)	0.0573 (10)
C1	0.5062 (6)	0.3838 (3)	0.2392 (5)	0.0292 (12)
C2	0.5405 (6)	0.4548 (3)	0.2512 (5)	0.0277 (12)
C3	0.5098 (7)	0.5105 (3)	0.1556 (6)	0.0326 (13)
H3	0.4560	0.5063	0.0537	0.039*
C4	0.5630 (8)	0.5711 (3)	0.2194 (6)	0.0409 (14)
C5	0.6451 (8)	0.5809 (3)	0.3707 (7)	0.0438 (16)
H5	0.6773	0.6240	0.4072	0.053*
C6	0.6775 (7)	0.5265 (3)	0.4641 (7)	0.0388 (14)
H6	0.7324	0.5311	0.5656	0.047*
C7	0.6260 (7)	0.4647 (3)	0.4027 (6)	0.0323 (13)
C8	0.5701 (7)	0.3559 (3)	0.3777 (6)	0.0321 (13)
C9	0.5796 (8)	0.2868 (3)	0.4372 (6)	0.0403 (15)
H9A	0.5129	0.2842	0.5183	0.048*
H9B	0.7065	0.2747	0.4742	0.048*
H9C	0.5257	0.2563	0.3582	0.048*
C10	0.5988 (7)	0.3223 (3)	−0.0108 (6)	0.0301 (13)
C11	0.6510 (7)	0.3687 (3)	−0.1085 (6)	0.0390 (14)
H11	0.5833	0.4080	−0.1342	0.047*
C12	0.8080 (7)	0.3549 (3)	−0.1675 (6)	0.0412 (15)
H12	0.8470	0.3854	−0.2330	0.049*
C13	0.9051 (8)	0.2966 (4)	−0.1293 (7)	0.0495 (17)
H13	1.0108	0.2881	−0.1679	0.059*
C14	0.8482 (8)	0.2507 (3)	−0.0353 (7)	0.0452 (15)
H14	0.9139	0.2109	−0.0119	0.054*
C15	0.6935 (7)	0.2634 (3)	0.0255 (6)	0.0394 (14)
H15	0.6544	0.2323	0.0898	0.047*
C16	0.1980 (6)	0.5209 (3)	0.4988 (5)	0.0275 (11)
C17	0.1588 (7)	0.4501 (3)	0.4804 (6)	0.0300 (12)
C18	0.1820 (7)	0.3933 (3)	0.5702 (6)	0.0341 (14)
H18	0.2355	0.3952	0.6725	0.041*
C19	0.1217 (7)	0.3339 (3)	0.5001 (7)	0.0366 (14)
C20	0.0419 (8)	0.3273 (3)	0.3496 (7)	0.0431 (15)
H20	0.0051	0.2852	0.3094	0.052*
C21	0.0171 (7)	0.3837 (3)	0.2591 (6)	0.0409 (14)
H21	−0.0357	0.3812	0.1568	0.049*
C22	0.0738 (7)	0.4434 (3)	0.3272 (6)	0.0320 (13)
C23	0.1387 (7)	0.5516 (3)	0.3642 (6)	0.0327 (13)
C24	0.1323 (8)	0.6216 (3)	0.3081 (7)	0.0478 (16)
H24A	0.0060	0.6345	0.2711	0.057*
H24B	0.1999	0.6247	0.2278	0.057*
H24C	0.1867	0.6511	0.3890	0.057*
C25	0.0987 (7)	0.5777 (3)	0.7488 (6)	0.0293 (13)
C26	0.0476 (7)	0.5332 (3)	0.8495 (6)	0.0375 (14)
H26	0.1157	0.4941	0.8776	0.045*
C27	−0.1081 (8)	0.5478 (3)	0.9085 (7)	0.0490 (17)
H27	−0.1435	0.5187	0.9786	0.059*
C28	−0.2091 (8)	0.6040 (3)	0.8651 (7)	0.0461 (17)
H28	−0.3129	0.6131	0.9057	0.055*
C29	−0.1597 (8)	0.6481 (3)	0.7610 (7)	0.0434 (15)
H29	−0.2305	0.6863	0.7310	0.052*
C30	−0.0042 (7)	0.6347 (3)	0.7022 (6)	0.0385 (13)
H30	0.0307	0.6637	0.6319	0.046*

	U11	U22	U33	U12	U13	U23
S1	0.0254 (7)	0.0406 (8)	0.0272 (7)	−0.0029 (6)	0.0021 (5)	−0.0014 (6)
S2	0.0266 (7)	0.0380 (8)	0.0283 (7)	−0.0013 (6)	0.0019 (5)	−0.0018 (6)
O1	0.039 (2)	0.041 (3)	0.025 (2)	0.0029 (17)	0.0014 (16)	0.0001 (18)
O2	0.029 (2)	0.046 (3)	0.032 (2)	0.0034 (18)	−0.0032 (16)	−0.0049 (19)
O3	0.041 (2)	0.047 (3)	0.037 (2)	−0.0117 (18)	0.0056 (18)	0.0009 (19)
O4	0.040 (2)	0.047 (3)	0.027 (2)	0.0071 (18)	0.0053 (16)	0.0018 (19)
O5	0.035 (2)	0.039 (2)	0.045 (2)	−0.0052 (18)	0.0084 (17)	−0.0042 (19)
O6	0.030 (2)	0.046 (2)	0.033 (2)	0.0040 (17)	0.0001 (16)	0.0034 (19)
F1	0.083 (3)	0.043 (2)	0.057 (2)	0.0025 (19)	0.0235 (19)	0.0091 (18)
F2	0.083 (3)	0.043 (2)	0.047 (2)	−0.0026 (18)	0.0171 (19)	0.0020 (17)
C1	0.019 (3)	0.041 (4)	0.025 (3)	−0.002 (2)	0.001 (2)	−0.001 (2)
C2	0.020 (3)	0.043 (4)	0.020 (3)	−0.001 (2)	0.005 (2)	−0.004 (2)
C3	0.032 (3)	0.041 (4)	0.025 (3)	0.002 (2)	0.006 (2)	−0.001 (3)
C4	0.046 (3)	0.037 (4)	0.042 (3)	0.004 (3)	0.016 (3)	0.005 (3)
C5	0.041 (3)	0.046 (4)	0.047 (4)	−0.006 (3)	0.015 (3)	−0.012 (3)
C6	0.033 (3)	0.053 (4)	0.030 (3)	−0.004 (3)	0.006 (2)	−0.014 (3)
C7	0.026 (3)	0.046 (4)	0.025 (3)	0.002 (2)	0.005 (2)	−0.002 (3)
C8	0.026 (3)	0.038 (4)	0.032 (3)	0.004 (2)	0.006 (2)	−0.001 (3)
C9	0.043 (4)	0.047 (4)	0.028 (3)	−0.003 (3)	0.001 (3)	0.006 (3)
C10	0.030 (3)	0.043 (4)	0.016 (2)	−0.002 (2)	0.000 (2)	−0.004 (2)
C11	0.035 (3)	0.053 (4)	0.027 (3)	−0.004 (3)	−0.001 (2)	−0.002 (3)
C12	0.036 (3)	0.071 (5)	0.015 (3)	−0.009 (3)	0.002 (2)	−0.001 (3)
C13	0.038 (4)	0.074 (5)	0.037 (4)	0.004 (3)	0.011 (3)	−0.010 (3)
C14	0.042 (3)	0.054 (4)	0.036 (3)	0.012 (3)	−0.001 (3)	−0.010 (3)
C15	0.036 (3)	0.044 (4)	0.038 (3)	0.002 (3)	0.006 (3)	−0.011 (3)
C16	0.025 (3)	0.034 (3)	0.024 (3)	0.003 (2)	0.004 (2)	0.003 (2)
C17	0.019 (3)	0.040 (4)	0.031 (3)	0.003 (2)	0.004 (2)	0.001 (2)
C18	0.033 (3)	0.041 (4)	0.030 (3)	−0.001 (2)	0.008 (2)	0.000 (3)
C19	0.033 (3)	0.035 (4)	0.042 (3)	0.000 (3)	0.010 (3)	0.005 (3)
C20	0.038 (3)	0.050 (4)	0.040 (3)	−0.009 (3)	0.006 (3)	−0.012 (3)
C21	0.039 (3)	0.057 (4)	0.026 (3)	0.000 (3)	0.005 (2)	−0.011 (3)
C22	0.027 (3)	0.045 (4)	0.024 (3)	0.002 (2)	0.005 (2)	−0.001 (3)
C23	0.030 (3)	0.039 (4)	0.031 (3)	0.001 (2)	0.012 (2)	0.000 (3)
C24	0.054 (4)	0.051 (4)	0.040 (4)	0.015 (3)	0.013 (3)	0.007 (3)
C25	0.023 (3)	0.039 (4)	0.024 (3)	−0.002 (2)	0.001 (2)	−0.007 (3)
C26	0.027 (3)	0.054 (4)	0.029 (3)	−0.003 (2)	−0.001 (2)	0.003 (3)
C27	0.036 (3)	0.081 (5)	0.031 (3)	−0.004 (3)	0.008 (3)	0.004 (3)
C28	0.031 (3)	0.077 (5)	0.029 (3)	−0.004 (3)	0.002 (3)	−0.023 (3)
C29	0.035 (3)	0.043 (4)	0.050 (4)	0.009 (3)	0.003 (3)	−0.011 (3)
C30	0.043 (3)	0.034 (3)	0.041 (3)	0.000 (3)	0.013 (3)	−0.001 (3)

S1—O3	1.424 (4)	C12—C13	1.368 (8)
S1—O2	1.432 (4)	C12—H12	0.9300
S1—C1	1.744 (5)	C13—C14	1.365 (8)
S1—C10	1.764 (6)	C13—H13	0.9300
S2—O5	1.426 (4)	C14—C15	1.383 (8)
S2—O6	1.430 (4)	C14—H14	0.9300
S2—C16	1.738 (5)	C15—H15	0.9300
S2—C25	1.759 (5)	C16—C23	1.352 (7)
O1—C8	1.364 (6)	C16—C17	1.437 (7)
O1—C7	1.375 (6)	C17—C18	1.378 (7)
O4—C22	1.369 (6)	C17—C22	1.408 (7)
O4—C23	1.377 (6)	C18—C19	1.369 (8)
F1—C4	1.363 (6)	C18—H18	0.9300
F2—C19	1.371 (7)	C19—C20	1.377 (8)
C1—C8	1.364 (7)	C20—C21	1.375 (8)
C1—C2	1.431 (7)	C20—H20	0.9300
C2—C3	1.392 (7)	C21—C22	1.361 (8)
C2—C7	1.402 (7)	C21—H21	0.9300
C3—C4	1.357 (8)	C23—C24	1.474 (7)
C3—H3	0.9300	C24—H24A	0.9600
C4—C5	1.393 (8)	C24—H24B	0.9600
C5—C6	1.361 (8)	C24—H24C	0.9600
C5—H5	0.9300	C25—C26	1.372 (7)
C6—C7	1.368 (8)	C25—C30	1.381 (7)
C6—H6	0.9300	C26—C27	1.389 (8)
C8—C9	1.469 (8)	C26—H26	0.9300
C9—H9A	0.9600	C27—C28	1.356 (8)
C9—H9B	0.9600	C27—H27	0.9300
C9—H9C	0.9600	C28—C29	1.383 (8)
C10—C15	1.368 (7)	C28—H28	0.9300
C10—C11	1.380 (8)	C29—C30	1.381 (8)
C11—C12	1.394 (8)	C29—H29	0.9300
C11—H11	0.9300	C30—H30	0.9300
O3—S1—O2	120.0 (2)	C12—C13—H13	119.7
O3—S1—C1	108.8 (2)	C13—C14—C15	120.3 (6)
O2—S1—C1	106.9 (2)	C13—C14—H14	119.8
O3—S1—C10	107.7 (2)	C15—C14—H14	119.8
O2—S1—C10	108.3 (2)	C10—C15—C14	118.8 (6)
C1—S1—C10	104.1 (2)	C10—C15—H15	120.6
O5—S2—O6	119.7 (2)	C14—C15—H15	120.6
O5—S2—C16	109.3 (2)	C23—C16—C17	108.3 (4)
O6—S2—C16	107.3 (2)	C23—C16—S2	126.0 (4)
O5—S2—C25	107.5 (2)	C17—C16—S2	125.6 (4)
O6—S2—C25	108.4 (2)	C18—C17—C22	118.7 (5)
C16—S2—C25	103.5 (2)	C18—C17—C16	137.1 (5)
C8—O1—C7	106.9 (4)	C22—C17—C16	104.3 (4)
C22—O4—C23	107.2 (4)	C19—C18—C17	116.1 (5)
C8—C1—C2	107.8 (4)	C19—C18—H18	122.0
C8—C1—S1	126.5 (4)	C17—C18—H18	122.0
C2—C1—S1	125.7 (4)	C18—C19—F2	118.0 (5)
C3—C2—C7	118.7 (5)	C18—C19—C20	125.1 (6)
C3—C2—C1	136.7 (5)	F2—C19—C20	116.9 (5)
C7—C2—C1	104.5 (4)	C21—C20—C19	119.3 (6)
C4—C3—C2	116.2 (5)	C21—C20—H20	120.3
C4—C3—H3	121.9	C19—C20—H20	120.3
C2—C3—H3	121.9	C22—C21—C20	116.4 (5)
C3—C4—F1	118.1 (5)	C22—C21—H21	121.8
C3—C4—C5	125.0 (6)	C20—C21—H21	121.8
F1—C4—C5	116.9 (6)	C21—C22—O4	125.5 (5)
C6—C5—C4	119.1 (6)	C21—C22—C17	124.4 (5)
C6—C5—H5	120.5	O4—C22—C17	110.1 (5)
C4—C5—H5	120.5	C16—C23—O4	110.0 (4)
C5—C6—C7	117.2 (5)	C16—C23—C24	135.6 (5)
C5—C6—H6	121.4	O4—C23—C24	114.3 (5)
C7—C6—H6	121.4	C23—C24—H24A	109.5
C6—C7—O1	125.8 (5)	C23—C24—H24B	109.5
C6—C7—C2	123.8 (5)	H24A—C24—H24B	109.5
O1—C7—C2	110.4 (5)	C23—C24—H24C	109.5
C1—C8—O1	110.5 (5)	H24A—C24—H24C	109.5
C1—C8—C9	134.2 (5)	H24B—C24—H24C	109.5
O1—C8—C9	115.3 (4)	C26—C25—C30	121.5 (5)
C8—C9—H9A	109.5	C26—C25—S2	120.2 (4)
C8—C9—H9B	109.5	C30—C25—S2	118.2 (4)
H9A—C9—H9B	109.5	C25—C26—C27	118.4 (5)
C8—C9—H9C	109.5	C25—C26—H26	120.8
H9A—C9—H9C	109.5	C27—C26—H26	120.8
H9B—C9—H9C	109.5	C28—C27—C26	120.6 (6)
C15—C10—C11	121.9 (5)	C28—C27—H27	119.7
C15—C10—S1	119.1 (4)	C26—C27—H27	119.7
C11—C10—S1	119.0 (4)	C27—C28—C29	120.9 (6)
C10—C11—C12	118.1 (6)	C27—C28—H28	119.6
C10—C11—H11	120.9	C29—C28—H28	119.6
C12—C11—H11	120.9	C30—C29—C28	119.3 (6)
C13—C12—C11	120.1 (6)	C30—C29—H29	120.4
C13—C12—H12	119.9	C28—C29—H29	120.4
C11—C12—H12	119.9	C25—C30—C29	119.3 (5)
C14—C13—C12	120.7 (6)	C25—C30—H30	120.4
C14—C13—H13	119.7	C29—C30—H30	120.4
O3—S1—C1—C8	24.1 (5)	O5—S2—C16—C23	−24.0 (5)
O2—S1—C1—C8	155.0 (4)	O6—S2—C16—C23	−155.2 (4)
C10—S1—C1—C8	−90.6 (5)	C25—S2—C16—C23	90.3 (5)
O3—S1—C1—C2	−158.9 (4)	O5—S2—C16—C17	160.2 (4)
O2—S1—C1—C2	−28.0 (5)	O6—S2—C16—C17	29.1 (5)
C10—S1—C1—C2	86.5 (5)	C25—S2—C16—C17	−85.5 (4)
C8—C1—C2—C3	−179.6 (6)	C23—C16—C17—C18	−179.4 (6)
S1—C1—C2—C3	2.8 (8)	S2—C16—C17—C18	−3.0 (8)
C8—C1—C2—C7	−0.1 (5)	C23—C16—C17—C22	−0.1 (5)
S1—C1—C2—C7	−177.6 (4)	S2—C16—C17—C22	176.3 (4)
C7—C2—C3—C4	−1.4 (7)	C22—C17—C18—C19	1.1 (7)
C1—C2—C3—C4	178.1 (5)	C16—C17—C18—C19	−179.7 (5)
C2—C3—C4—F1	−178.5 (4)	C17—C18—C19—F2	178.5 (4)
C2—C3—C4—C5	0.3 (8)	C17—C18—C19—C20	0.2 (8)
C3—C4—C5—C6	0.5 (9)	C18—C19—C20—C21	−0.5 (9)
F1—C4—C5—C6	179.3 (5)	F2—C19—C20—C21	−178.9 (5)
C4—C5—C6—C7	−0.2 (8)	C19—C20—C21—C22	−0.4 (8)
C5—C6—C7—O1	−178.2 (5)	C20—C21—C22—O4	179.2 (5)
C5—C6—C7—C2	−0.9 (8)	C20—C21—C22—C17	1.7 (8)
C8—O1—C7—C6	178.1 (5)	C23—O4—C22—C21	−178.6 (5)
C8—O1—C7—C2	0.5 (5)	C23—O4—C22—C17	−0.9 (5)
C3—C2—C7—C6	1.8 (7)	C18—C17—C22—C21	−2.1 (8)
C1—C2—C7—C6	−177.9 (5)	C16—C17—C22—C21	178.4 (5)
C3—C2—C7—O1	179.4 (4)	C18—C17—C22—O4	−179.9 (4)
C1—C2—C7—O1	−0.3 (5)	C16—C17—C22—O4	0.6 (5)
C2—C1—C8—O1	0.4 (5)	C17—C16—C23—O4	−0.5 (5)
S1—C1—C8—O1	177.9 (3)	S2—C16—C23—O4	−176.8 (3)
C2—C1—C8—C9	−178.3 (5)	C17—C16—C23—C24	177.9 (5)
S1—C1—C8—C9	−0.8 (8)	S2—C16—C23—C24	1.5 (9)
C7—O1—C8—C1	−0.6 (5)	C22—O4—C23—C16	0.9 (5)
C7—O1—C8—C9	178.4 (4)	C22—O4—C23—C24	−177.9 (4)
O3—S1—C10—C15	−26.1 (5)	O5—S2—C25—C26	−150.5 (4)
O2—S1—C10—C15	−157.2 (4)	O6—S2—C25—C26	−19.8 (5)
C1—S1—C10—C15	89.3 (5)	C16—S2—C25—C26	93.9 (4)
O3—S1—C10—C11	155.8 (4)	O5—S2—C25—C30	32.8 (5)
O2—S1—C10—C11	24.6 (5)	O6—S2—C25—C30	163.5 (4)
C1—S1—C10—C11	−88.8 (4)	C16—S2—C25—C30	−82.8 (5)
C15—C10—C11—C12	−1.8 (8)	C30—C25—C26—C27	−2.2 (8)
S1—C10—C11—C12	176.3 (4)	S2—C25—C26—C27	−178.8 (4)
C10—C11—C12—C13	0.5 (8)	C25—C26—C27—C28	1.3 (8)
C11—C12—C13—C14	1.0 (9)	C26—C27—C28—C29	0.1 (9)
C12—C13—C14—C15	−1.4 (9)	C27—C28—C29—C30	−0.7 (9)
C11—C10—C15—C14	1.4 (8)	C26—C25—C30—C29	1.6 (8)
S1—C10—C15—C14	−176.7 (4)	S2—C25—C30—C29	178.3 (4)
C13—C14—C15—C10	0.2 (8)	C28—C29—C30—C25	−0.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6i	0.93	2.60	3.494 (6)	162
C26—H26···O2ii	0.93	2.55	3.479 (7)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O6i	0.93	2.60	3.494 (6)	162
C26—H26⋯O2ii	0.93	2.55	3.479 (7)	174

Symmetry codes: (i) ; (ii) .