3-Cyclo-pentyl-sulfonyl-5-fluoro-2-methyl-1-benzofuran.

There are two independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(14)H(15)FO(3)S, in each of which the cyclo-pentyl ring adopts an envelope conformation. The benzofuran units in each mol-ecule are essentially planar, with mean deviations from the least-squares plane defined by the nine constituent ring atoms of 0.009 (2) Å for mol-ecule A and 0.013 (2) Å for mol-ecule B. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds. In the cyclo-pentyl ring of mol-ecule B, one C atom is disordered over two positions with site-occupancy factors of 0.60 (2) and 0.40 (2).

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For a structural study of the related compound 5-bromo-3-cyclo­pentyl­sulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011 ▶).

Experimental

Crystal data

C14H15FO3S

M = 282.32

Triclinic,

a = 10.0568 (8) Å

b = 10.2697 (8) Å

c = 13.2894 (10) Å

α = 95.033 (4)°

β = 109.140 (4)°

γ = 91.229 (4)°

V = 1289.82 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.936, T max = 0.948

21777 measured reflections

5565 independent reflections

4022 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.03

5565 reflections

361 parameters

20 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.31 e Å−3

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 datablock(s) global, I. DOI: 10.1107/S1600536811021222/go2016sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021222/go2016Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021222/go2016Isup3.cml

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

C14H15FO3S	Z = 4
Mr = 282.32	F(000) = 592
Triclinic, P1	Dx = 1.454 Mg m−3
Hall symbol: -P 1	Melting point = 394–395 K
a = 10.0568 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2697 (8) Å	Cell parameters from 6383 reflections
c = 13.2894 (10) Å	θ = 2.2–28.1°
α = 95.033 (4)°	µ = 0.26 mm−1
β = 109.140 (4)°	T = 173 K
γ = 91.229 (4)°	Block, colourless
V = 1289.82 (17) Å3	0.26 × 0.24 × 0.20 mm

Bruker SMART APEXII CCD diffractometer	5565 independent reflections
Radiation source: rotating anode	4022 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.042
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.6°
φ and ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.936, Tmax = 0.948	l = −16→16
21777 measured 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.6137P] where P = (Fo2 + 2Fc2)/3
5565 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.50 e Å−3
20 restraints	Δρmin = −0.31 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	Occ. (<1)
S1	0.23453 (6)	0.33785 (5)	0.23641 (4)	0.03150 (15)
F1	0.81952 (14)	0.46170 (14)	0.28853 (11)	0.0484 (4)
O1	0.40319 (15)	0.10269 (14)	0.07061 (11)	0.0326 (4)
O2	0.09116 (17)	0.32983 (18)	0.16639 (13)	0.0460 (4)
C1	0.3369 (2)	0.2567 (2)	0.17088 (16)	0.0269 (4)
C2	0.4835 (2)	0.28575 (19)	0.18530 (15)	0.0252 (4)
O3	0.30185 (18)	0.46418 (15)	0.27859 (14)	0.0438 (4)
C3	0.5859 (2)	0.3822 (2)	0.24350 (16)	0.0296 (5)
H3	0.5664	0.4524	0.2872	0.036*
C4	0.7165 (2)	0.3693 (2)	0.23369 (17)	0.0311 (5)
C5	0.7522 (2)	0.2698 (2)	0.17204 (18)	0.0344 (5)
H5	0.8456	0.2666	0.1699	0.041*
C6	0.6504 (2)	0.1750 (2)	0.11357 (17)	0.0333 (5)
H6	0.6704	0.1051	0.0699	0.040*
C7	0.5185 (2)	0.1872 (2)	0.12172 (16)	0.0280 (5)
C8	0.2955 (2)	0.1465 (2)	0.10210 (16)	0.0305 (5)
C9	0.1621 (2)	0.0657 (2)	0.05858 (19)	0.0411 (6)
H9A	0.1435	0.0392	−0.0177	0.062*
H9B	0.0847	0.1166	0.0675	0.062*
H9C	0.1697	−0.0125	0.0971	0.062*
C10	0.2422 (2)	0.2431 (2)	0.34337 (17)	0.0310 (5)
H10	0.2079	0.1510	0.3140	0.037*
C11	0.3910 (3)	0.2436 (2)	0.42411 (18)	0.0396 (6)
H11A	0.4133	0.1548	0.4460	0.048*
H11B	0.4617	0.2748	0.3933	0.048*
C12	0.3888 (3)	0.3373 (3)	0.5190 (2)	0.0514 (7)
H12A	0.4612	0.3171	0.5860	0.062*
H12B	0.4047	0.4293	0.5070	0.062*
C13	0.2438 (3)	0.3130 (3)	0.5228 (2)	0.0510 (7)
H13A	0.2174	0.3868	0.5643	0.061*
H13B	0.2374	0.2315	0.5560	0.061*
C14	0.1491 (3)	0.3006 (2)	0.40645 (19)	0.0405 (6)
H14A	0.1171	0.3872	0.3839	0.049*
H14B	0.0654	0.2414	0.3954	0.049*
S2	0.97507 (6)	0.86902 (6)	0.24244 (5)	0.03691 (16)
F2	0.43771 (16)	0.96231 (15)	0.28861 (13)	0.0589 (4)
O4	0.67248 (16)	0.60770 (14)	0.08407 (12)	0.0359 (4)
O5	0.93729 (18)	1.00229 (16)	0.24654 (16)	0.0536 (5)
O6	1.07814 (18)	0.83460 (19)	0.19339 (15)	0.0534 (5)
C15	0.8217 (2)	0.7728 (2)	0.17896 (17)	0.0308 (5)
C16	0.6865 (2)	0.7948 (2)	0.19121 (16)	0.0290 (5)
C17	0.6327 (2)	0.8908 (2)	0.24526 (17)	0.0332 (5)
H17	0.6884	0.9657	0.2853	0.040*
C18	0.4942 (3)	0.8703 (2)	0.23702 (19)	0.0399 (6)
C19	0.4080 (3)	0.7648 (2)	0.1794 (2)	0.0424 (6)
H19	0.3129	0.7566	0.1776	0.051*
C20	0.4606 (2)	0.6713 (2)	0.12428 (19)	0.0387 (5)
H20	0.4039	0.5976	0.0830	0.046*
C21	0.5994 (2)	0.6900 (2)	0.13206 (17)	0.0312 (5)
C22	0.8073 (2)	0.6592 (2)	0.11486 (17)	0.0334 (5)
C23	0.9032 (3)	0.5815 (3)	0.0738 (2)	0.0456 (6)
H23A	0.9124	0.4962	0.1026	0.068*
H23B	0.9960	0.6279	0.0961	0.068*
H23C	0.8650	0.5686	−0.0045	0.068*
C24	1.0323 (2)	0.8246 (2)	0.37518 (18)	0.0367 (5)
H24	0.9527	0.8329	0.4044	0.044*
C25	1.1571 (3)	0.9139 (3)	0.4469 (2)	0.0526 (7)
H25A	1.2183	0.9408	0.4064	0.063*
H25B	1.1246	0.9932	0.4779	0.063*
C26	1.2325 (3)	0.8310 (2)	0.5315 (2)	0.0665 (9)
H26A	1.1804	0.8185	0.5819	0.080*	0.60 (2)
H26B	1.3293	0.8672	0.5719	0.080*	0.60 (2)
H26C	1.1987	0.8460	0.5934	0.080*	0.40 (2)
H26D	1.3349	0.8542	0.5562	0.080*	0.40 (2)
C27A	1.2327 (6)	0.7051 (8)	0.4620 (8)	0.060 (3)	0.60 (2)
H27A	1.3006	0.7139	0.4230	0.072*	0.60 (2)
H27B	1.2574	0.6306	0.5058	0.072*	0.60 (2)
C27B	1.1998 (14)	0.6866 (3)	0.4914 (7)	0.050 (3)	0.40 (2)
H27C	1.2837	0.6453	0.4824	0.060*	0.40 (2)
H27D	1.1679	0.6392	0.5419	0.060*	0.40 (2)
C28	1.0829 (3)	0.6861 (2)	0.3846 (2)	0.0429 (6)
H28A	1.0237	0.6318	0.4132	0.051*	0.60 (2)
H28B	1.0810	0.6439	0.3142	0.051*	0.60 (2)
H28C	1.012 (7)	0.612 (7)	0.354 (5)	0.051*	0.40 (2)
H28D	1.134 (8)	0.675 (7)	0.343 (5)	0.051*	0.40 (2)

	U11	U22	U33	U12	U13	U23
S1	0.0255 (3)	0.0333 (3)	0.0406 (3)	0.0073 (2)	0.0156 (2)	0.0095 (2)
F1	0.0306 (8)	0.0513 (8)	0.0585 (9)	−0.0166 (6)	0.0147 (7)	−0.0158 (7)
O1	0.0280 (8)	0.0345 (8)	0.0335 (8)	−0.0066 (6)	0.0106 (7)	−0.0059 (6)
O2	0.0253 (9)	0.0664 (12)	0.0505 (10)	0.0139 (8)	0.0136 (8)	0.0204 (9)
C1	0.0210 (10)	0.0323 (11)	0.0289 (11)	0.0036 (8)	0.0093 (8)	0.0064 (9)
C2	0.0241 (11)	0.0269 (10)	0.0266 (10)	0.0031 (8)	0.0103 (8)	0.0048 (8)
O3	0.0478 (10)	0.0284 (8)	0.0672 (11)	0.0050 (7)	0.0350 (9)	0.0058 (8)
C3	0.0292 (12)	0.0291 (11)	0.0305 (11)	−0.0005 (9)	0.0112 (9)	−0.0016 (9)
C4	0.0240 (11)	0.0318 (11)	0.0347 (11)	−0.0067 (9)	0.0073 (9)	−0.0002 (9)
C5	0.0247 (11)	0.0387 (12)	0.0418 (13)	0.0011 (9)	0.0139 (10)	0.0036 (10)
C6	0.0328 (12)	0.0321 (11)	0.0370 (12)	0.0025 (9)	0.0160 (10)	−0.0029 (9)
C7	0.0267 (11)	0.0287 (11)	0.0272 (10)	−0.0035 (9)	0.0079 (9)	0.0003 (8)
C8	0.0237 (11)	0.0380 (12)	0.0295 (11)	−0.0011 (9)	0.0079 (9)	0.0050 (9)
C9	0.0302 (13)	0.0490 (14)	0.0402 (13)	−0.0123 (11)	0.0086 (10)	−0.0014 (11)
C10	0.0313 (12)	0.0297 (11)	0.0353 (11)	0.0024 (9)	0.0153 (9)	0.0035 (9)
C11	0.0370 (13)	0.0476 (14)	0.0365 (12)	0.0095 (11)	0.0137 (10)	0.0082 (10)
C12	0.0499 (16)	0.0596 (17)	0.0428 (14)	−0.0057 (13)	0.0161 (12)	−0.0057 (12)
C13	0.0549 (17)	0.0577 (17)	0.0448 (15)	−0.0044 (13)	0.0266 (13)	−0.0091 (12)
C14	0.0375 (14)	0.0428 (13)	0.0483 (14)	0.0030 (11)	0.0240 (11)	0.0039 (11)
S2	0.0264 (3)	0.0356 (3)	0.0497 (4)	0.0012 (2)	0.0113 (3)	0.0147 (3)
F2	0.0464 (9)	0.0605 (10)	0.0742 (11)	0.0162 (8)	0.0294 (8)	−0.0092 (8)
O4	0.0350 (9)	0.0342 (8)	0.0360 (8)	0.0045 (7)	0.0096 (7)	−0.0021 (7)
O5	0.0420 (10)	0.0311 (9)	0.0794 (13)	−0.0014 (8)	0.0065 (9)	0.0158 (9)
O6	0.0326 (10)	0.0718 (13)	0.0651 (12)	0.0029 (9)	0.0248 (9)	0.0214 (10)
C15	0.0278 (12)	0.0328 (11)	0.0347 (11)	0.0066 (9)	0.0120 (9)	0.0098 (9)
C16	0.0262 (11)	0.0308 (11)	0.0301 (11)	0.0035 (9)	0.0081 (9)	0.0080 (9)
C17	0.0300 (12)	0.0311 (11)	0.0375 (12)	0.0031 (9)	0.0099 (10)	0.0024 (9)
C18	0.0388 (14)	0.0397 (13)	0.0444 (14)	0.0123 (11)	0.0176 (11)	0.0041 (11)
C19	0.0253 (12)	0.0509 (15)	0.0521 (15)	0.0053 (11)	0.0129 (11)	0.0109 (12)
C20	0.0291 (12)	0.0377 (13)	0.0443 (13)	−0.0010 (10)	0.0059 (10)	0.0023 (10)
C21	0.0307 (12)	0.0299 (11)	0.0325 (11)	0.0059 (9)	0.0095 (9)	0.0034 (9)
C22	0.0327 (12)	0.0372 (12)	0.0340 (12)	0.0086 (10)	0.0139 (10)	0.0102 (9)
C23	0.0499 (16)	0.0497 (15)	0.0450 (14)	0.0195 (12)	0.0246 (12)	0.0076 (11)
C24	0.0318 (12)	0.0339 (12)	0.0417 (13)	−0.0020 (10)	0.0091 (10)	0.0031 (10)
C25	0.0480 (16)	0.0382 (14)	0.0609 (17)	−0.0087 (12)	0.0060 (13)	−0.0013 (12)
C26	0.0509 (18)	0.0546 (18)	0.069 (2)	0.0086 (14)	−0.0089 (15)	−0.0162 (15)
C27A	0.046 (3)	0.050 (3)	0.058 (4)	0.016 (3)	−0.013 (3)	−0.009 (3)
C27B	0.059 (6)	0.040 (4)	0.042 (4)	0.011 (4)	0.005 (4)	0.000 (3)
C28	0.0407 (15)	0.0318 (13)	0.0478 (15)	−0.0022 (11)	0.0034 (12)	0.0050 (11)

S1—O3	1.4289 (17)	F2—C18	1.360 (3)
S1—O2	1.4329 (17)	O4—C22	1.362 (3)
S1—C1	1.735 (2)	O4—C21	1.379 (3)
S1—C10	1.774 (2)	C15—C22	1.358 (3)
F1—C4	1.359 (2)	C15—C16	1.442 (3)
O1—C8	1.355 (3)	C16—C21	1.380 (3)
O1—C7	1.377 (2)	C16—C17	1.390 (3)
C1—C8	1.356 (3)	C17—C18	1.372 (3)
C1—C2	1.444 (3)	C17—H17	0.9500
C2—C7	1.387 (3)	C18—C19	1.375 (3)
C2—C3	1.392 (3)	C19—C20	1.375 (3)
C3—C4	1.370 (3)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.374 (3)
C4—C5	1.381 (3)	C20—H20	0.9500
C5—C6	1.379 (3)	C22—C23	1.471 (3)
C5—H5	0.9500	C23—H23A	0.9800
C6—C7	1.373 (3)	C23—H23B	0.9800
C6—H6	0.9500	C23—H23C	0.9800
C8—C9	1.478 (3)	C24—C28	1.523 (3)
C9—H9A	0.9800	C24—C25	1.529 (3)
C9—H9B	0.9800	C24—H24	1.0000
C9—H9C	0.9800	C25—C26	1.484 (4)
C10—C11	1.528 (3)	C25—H25A	0.9900
C10—C14	1.543 (3)	C25—H25B	0.9900
C10—H10	1.0000	C26—C27B	1.522 (2)
C11—C12	1.524 (3)	C26—C27A	1.522 (2)
C11—H11A	0.9900	C26—H26A	0.9900
C11—H11B	0.9900	C26—H26B	0.9900
C12—C13	1.492 (4)	C26—H26C	0.9900
C12—H12A	0.9900	C26—H26D	0.9900
C12—H12B	0.9900	C27A—C28	1.5166 (18)
C13—C14	1.520 (3)	C27A—H27A	0.9900
C13—H13A	0.9900	C27A—H27B	0.9900
C13—H13B	0.9900	C27B—C28	1.5171 (18)
C14—H14A	0.9900	C27B—H27C	0.9900
C14—H14B	0.9900	C27B—H27D	0.9900
S2—O6	1.4292 (19)	C28—H28A	0.9900
S2—O5	1.4294 (18)	C28—H28B	0.9900
S2—C15	1.733 (2)	C28—H28C	0.99 (7)
S2—C24	1.771 (2)	C28—H28D	0.87 (7)
O3—S1—O2	118.65 (11)	F2—C18—C19	117.8 (2)
O3—S1—C1	107.46 (10)	C17—C18—C19	124.8 (2)
O2—S1—C1	108.81 (10)	C20—C19—C18	119.4 (2)
O3—S1—C10	109.46 (10)	C20—C19—H19	120.3
O2—S1—C10	107.34 (10)	C18—C19—H19	120.3
C1—S1—C10	104.18 (10)	C21—C20—C19	116.5 (2)
C8—O1—C7	107.10 (15)	C21—C20—H20	121.7
C8—C1—C2	107.13 (19)	C19—C20—H20	121.7
C8—C1—S1	125.44 (16)	C20—C21—O4	125.7 (2)
C2—C1—S1	127.23 (16)	C20—C21—C16	124.1 (2)
C7—C2—C3	119.14 (19)	O4—C21—C16	110.18 (19)
C7—C2—C1	104.77 (17)	C15—C22—O4	110.5 (2)
C3—C2—C1	136.1 (2)	C15—C22—C23	134.7 (2)
C4—C3—C2	115.69 (19)	O4—C22—C23	114.8 (2)
C4—C3—H3	122.2	C22—C23—H23A	109.5
C2—C3—H3	122.2	C22—C23—H23B	109.5
F1—C4—C3	117.72 (19)	H23A—C23—H23B	109.5
F1—C4—C5	117.06 (19)	C22—C23—H23C	109.5
C3—C4—C5	125.22 (19)	H23A—C23—H23C	109.5
C6—C5—C4	119.1 (2)	H23B—C23—H23C	109.5
C6—C5—H5	120.5	C28—C24—C25	105.42 (19)
C4—C5—H5	120.5	C28—C24—S2	113.88 (17)
C7—C6—C5	116.5 (2)	C25—C24—S2	111.11 (17)
C7—C6—H6	121.8	C28—C24—H24	108.8
C5—C6—H6	121.8	C25—C24—H24	108.8
C6—C7—O1	125.45 (19)	S2—C24—H24	108.8
C6—C7—C2	124.39 (19)	C26—C25—C24	103.5 (2)
O1—C7—C2	110.14 (18)	C26—C25—H25A	111.1
O1—C8—C1	110.84 (17)	C24—C25—H25A	111.1
O1—C8—C9	115.52 (19)	C26—C25—H25B	111.1
C1—C8—C9	133.6 (2)	C24—C25—H25B	111.1
C8—C9—H9A	109.5	H25A—C25—H25B	109.0
C8—C9—H9B	109.5	C25—C26—C27B	110.6 (2)
H9A—C9—H9B	109.5	C25—C26—C27A	99.5 (5)
C8—C9—H9C	109.5	C25—C26—H26A	111.9
H9A—C9—H9C	109.5	C27B—C26—H26A	88.1
H9B—C9—H9C	109.5	C27A—C26—H26A	111.9
C11—C10—C14	106.14 (18)	C25—C26—H26B	111.9
C11—C10—S1	112.41 (15)	C27B—C26—H26B	122.4
C14—C10—S1	110.05 (16)	C27A—C26—H26B	111.9
C11—C10—H10	109.4	H26A—C26—H26B	109.6
C14—C10—H10	109.4	C25—C26—H26C	109.7
S1—C10—H10	109.4	C27B—C26—H26C	106.2
C12—C11—C10	104.7 (2)	C27A—C26—H26C	129.9
C12—C11—H11A	110.8	H26B—C26—H26C	94.1
C10—C11—H11A	110.8	C25—C26—H26D	110.0
C12—C11—H11B	110.8	C27B—C26—H26D	111.9
C10—C11—H11B	110.8	C27A—C26—H26D	98.1
H11A—C11—H11B	108.9	H26A—C26—H26D	122.4
C13—C12—C11	103.0 (2)	H26C—C26—H26D	108.3
C13—C12—H12A	111.2	C28—C27A—C26	104.3 (2)
C11—C12—H12A	111.2	C28—C27A—H27A	110.9
C13—C12—H12B	111.2	C26—C27A—H27A	110.9
C11—C12—H12B	111.2	C28—C27A—H27B	110.9
H12A—C12—H12B	109.1	C26—C27A—H27B	110.9
C12—C13—C14	104.7 (2)	H27A—C27A—H27B	108.9
C12—C13—H13A	110.8	C26—C27A—H28D	124 (3)
C14—C13—H13A	110.8	H27A—C27A—H28D	78.9
C12—C13—H13B	110.8	H27B—C27A—H28D	117.5
C14—C13—H13B	110.8	C28—C27B—C26	104.3 (2)
H13A—C13—H13B	108.9	C28—C27B—H27C	110.9
C13—C14—C10	104.66 (19)	C26—C27B—H27C	110.9
C13—C14—H14A	110.8	C28—C27B—H27D	110.9
C10—C14—H14A	110.8	C26—C27B—H27D	110.9
C13—C14—H14B	110.8	H27C—C27B—H27D	108.9
C10—C14—H14B	110.8	C27A—C28—C24	103.9 (3)
H14A—C14—H14B	108.9	C27B—C28—C24	107.6 (3)
O6—S2—O5	118.23 (11)	C27A—C28—H28A	111.0
O6—S2—C15	109.20 (11)	C27B—C28—H28A	88.1
O5—S2—C15	107.56 (10)	C24—C28—H28A	111.0
O6—S2—C24	109.04 (11)	C27A—C28—H28B	111.0
O5—S2—C24	107.64 (11)	C27B—C28—H28B	127.7
C15—S2—C24	104.28 (10)	C24—C28—H28B	111.0
C22—O4—C21	107.03 (16)	H28A—C28—H28B	109.0
C22—C15—C16	107.17 (19)	C27A—C28—H28C	137 (4)
C22—C15—S2	127.18 (18)	C27B—C28—H28C	123 (4)
C16—C15—S2	125.52 (17)	C24—C28—H28C	118 (4)
C21—C16—C17	119.4 (2)	H28A—C28—H28C	45.4
C21—C16—C15	105.14 (19)	H28B—C28—H28C	64.8
C17—C16—C15	135.4 (2)	C27A—C28—H28D	76 (4)
C18—C17—C16	115.7 (2)	C27B—C28—H28D	98 (5)
C18—C17—H17	122.2	C24—C28—H28D	107 (5)
C16—C17—H17	122.2	H28A—C28—H28D	137.9
F2—C18—C17	117.4 (2)	H28C—C28—H28D	100 (6)
O3—S1—C1—C8	−165.58 (19)	C24—S2—C15—C16	76.3 (2)
O2—S1—C1—C8	−35.9 (2)	C22—C15—C16—C21	0.1 (2)
C10—S1—C1—C8	78.3 (2)	S2—C15—C16—C21	−176.02 (16)
O3—S1—C1—C2	20.1 (2)	C22—C15—C16—C17	−180.0 (2)
O2—S1—C1—C2	149.75 (18)	S2—C15—C16—C17	3.9 (4)
C10—S1—C1—C2	−96.00 (19)	C21—C16—C17—C18	1.7 (3)
C8—C1—C2—C7	0.0 (2)	C15—C16—C17—C18	−178.2 (2)
S1—C1—C2—C7	175.20 (16)	C16—C17—C18—F2	−179.82 (19)
C8—C1—C2—C3	179.9 (2)	C16—C17—C18—C19	−0.8 (4)
S1—C1—C2—C3	−4.9 (4)	F2—C18—C19—C20	178.6 (2)
C7—C2—C3—C4	−1.0 (3)	C17—C18—C19—C20	−0.5 (4)
C1—C2—C3—C4	179.1 (2)	C18—C19—C20—C21	0.7 (3)
C2—C3—C4—F1	179.56 (18)	C19—C20—C21—O4	179.4 (2)
C2—C3—C4—C5	−0.2 (3)	C19—C20—C21—C16	0.3 (3)
F1—C4—C5—C6	−178.90 (19)	C22—O4—C21—C20	−177.9 (2)
C3—C4—C5—C6	0.9 (4)	C22—O4—C21—C16	1.3 (2)
C4—C5—C6—C7	−0.2 (3)	C17—C16—C21—C20	−1.6 (3)
C5—C6—C7—O1	−179.5 (2)	C15—C16—C21—C20	178.4 (2)
C5—C6—C7—C2	−1.1 (3)	C17—C16—C21—O4	179.21 (18)
C8—O1—C7—C6	178.1 (2)	C15—C16—C21—O4	−0.8 (2)
C8—O1—C7—C2	−0.5 (2)	C16—C15—C22—O4	0.7 (2)
C3—C2—C7—C6	1.8 (3)	S2—C15—C22—O4	176.73 (15)
C1—C2—C7—C6	−178.4 (2)	C16—C15—C22—C23	−178.4 (2)
C3—C2—C7—O1	−179.60 (17)	S2—C15—C22—C23	−2.4 (4)
C1—C2—C7—O1	0.3 (2)	C21—O4—C22—C15	−1.2 (2)
C7—O1—C8—C1	0.5 (2)	C21—O4—C22—C23	178.08 (18)
C7—O1—C8—C9	−177.92 (18)	O6—S2—C24—C28	−47.9 (2)
C2—C1—C8—O1	−0.3 (2)	O5—S2—C24—C28	−177.32 (17)
S1—C1—C8—O1	−175.62 (14)	C15—S2—C24—C28	68.63 (19)
C2—C1—C8—C9	177.7 (2)	O6—S2—C24—C25	70.9 (2)
S1—C1—C8—C9	2.4 (4)	O5—S2—C24—C25	−58.5 (2)
O3—S1—C10—C11	−50.09 (18)	C15—S2—C24—C25	−172.52 (18)
O2—S1—C10—C11	179.88 (16)	C28—C24—C25—C26	−29.6 (3)
C1—S1—C10—C11	64.59 (18)	S2—C24—C25—C26	−153.4 (2)
O3—S1—C10—C14	67.98 (17)	C24—C25—C26—C27B	23.9 (8)
O2—S1—C10—C14	−62.05 (17)	C24—C25—C26—C27A	45.8 (5)
C1—S1—C10—C14	−177.34 (15)	C25—C26—C27A—C28	−46.0 (9)
C14—C10—C11—C12	−17.1 (2)	C27B—C26—C27A—C28	74.3 (4)
S1—C10—C11—C12	103.3 (2)	C25—C26—C27B—C28	−8.7 (12)
C10—C11—C12—C13	36.0 (3)	C27A—C26—C27B—C28	−74.2 (4)
C11—C12—C13—C14	−41.4 (3)	C26—C27A—C28—C27B	−74.3 (4)
C12—C13—C14—C10	30.6 (3)	C26—C27A—C28—C24	27.8 (10)
C11—C10—C14—C13	−7.9 (2)	C26—C27B—C28—C27A	74.2 (4)
S1—C10—C14—C13	−129.75 (18)	C26—C27B—C28—C24	−10.5 (12)
O6—S2—C15—C22	17.4 (2)	C25—C24—C28—C27A	0.6 (7)
O5—S2—C15—C22	146.8 (2)	S2—C24—C28—C27A	122.7 (6)
C24—S2—C15—C22	−99.1 (2)	C25—C24—C28—C27B	25.2 (8)
O6—S2—C15—C16	−167.32 (18)	S2—C24—C28—C27B	147.2 (8)
O5—S2—C15—C16	−37.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O6i	0.98	2.45	3.348 (3)	152
C19—H19···O6ii	0.95	2.58	3.469 (3)	157
C23—H23A···O2iii	0.98	2.50	3.318 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O6i	0.98	2.45	3.348 (3)	152
C19—H19⋯O6ii	0.95	2.58	3.469 (3)	157
C23—H23A⋯O2iii	0.98	2.50	3.318 (3)	141

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