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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o258.
Published online 2010 January 9. doi:  10.1107/S1600536809055068
PMCID: PMC2979977

5-Fluoro-2-methyl-3-phenyl­sulfonyl-1-benzofuran

Abstract

There are two symmetry-independent mol­ecules, A and B, in the asymmetric unit of the title compound, C15H11FO3S. The crystal studied was an inversion twin with a 0.21 (12):0.79 (12) domain ratio. In the crystal structure, the two independent mol­ecules 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 mol­ecule A and 80.7 (1)° in mol­ecule B. In the crystal structure, the A and B mol­ecules are linked by aromatic π–π inter­actions 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 inter­molecular 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 [triangle],b [triangle],c [triangle]). For natural products with benzofuran ring systems, see: Akgul & Anil (2003 [triangle]); Soekamto et al. (2003 [triangle]). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 [triangle]); Galal et al. (2009 [triangle]).

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Object name is e-66-0o258-scheme1.jpg

Experimental

Crystal data

  • C15H11FO3S
  • M r = 290.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o258-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 1642 Friedel pairs
  • Flack parameter: 0.21 (12)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

supplementary crystallographic information

Comment

Molecules involving benzofuran skeleton have attracted considerable interest in the view of their presence in natural products (Akgul & Anil, 2003; Soekamto et al., 2003) and their biological activity (Aslam et al., 2006; Galal et al., 2009). As a part of our continuing studies of the effect of side chain substituents on the solid state structures of 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al., 2008a, b, c), we report the crystal structure of the title compound (Fig. 1). The crystal studied was an inversion twin with a 0.21 (12):0.79 (12) domain ratio. It crystallized in the monoclinic space group P21, with two symmetry-independent molecules, A and B, in the asymmetric unit.

The benzofuran unit is essentially planar, with a mean deviation of 0.011 (4) Å for A molecule and 0.007 (4) Å for B molecule, respectively, from the least-squares plane defined by the nine constituent atoms. In the title compound, the dihedral angles formed by the phenyl ring and the plane of the benzofuran fragment are 80.2 (1)° in molecule A and 80.7 (1)° in molecule B, respectively. In the crystal packing (Fig. 2), the A and B molecules are linked by two different aromatic π–π interactions; the first between the furan ring (Cg1) and an adjacent benzene ring (Cg4) [distance = 3.671 (7) Å], the second between the furan ring (Cg3) and an adjacent benzene ring (Cg2) [distance = 3.715 (7) Å], (Cg1, Cg2, Cg3, and Cg4 are the centroids of the C1/C2/C7/O1/C8 furan ring, the C2–C7 benzene ring, the C16/C17/C22/O4/C23 furan ring, and the C17–C22 benzene ring, respectively). The molecular packing (Fig. 2) is further stabilized by two non-classical intermolecular C—H···O hydrogen bonds; the first between the benzene H atom and the oxygen of the S═O unit, with a C3—H3···O6i, the second between the phenyl H atom and the oxygen of the S═O unit, with a C26—H26···O2ii, respectively (Table 1).

Experimental

77% 3-Chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 5-fluoro-2-methyl-3-phenylsulfanyl-1-benzofuran (310 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (chloroform) to afford the title compound as a colorless solid [yield 75%, m.p. 397–398 K; Rf = 0.55 (chloroform)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aromatic H atoms and 0.96 Å for methyl H atoms, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms and 1.5Ueq(C) for methyl H atoms. The reported Flack parameter was obtained by TWIN/BASF procedure in SHELXL (Sheldrick, 2008).

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
Fig. 2.
π–π and C—H···O interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) x, y, z - 1; (ii) x, y, z + 1.]

Crystal data

C15H11FO3SF(000) = 600
Mr = 290.30Dx = 1.490 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ybCell parameters from 2528 reflections
a = 7.377 (2) Åθ = 2.3–25.7°
b = 19.831 (4) ŵ = 0.27 mm1
c = 9.025 (2) ÅT = 173 K
β = 101.367 (3)°Block, colourless
V = 1294.4 (5) Å30.40 × 0.20 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEXII CCD diffractometer3996 independent reflections
Radiation source: Rotating Anode3154 reflections with I > 2σ(I)
HELIOSRint = 0.062
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 2.1°
[var phi] and ω scansh = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −19→23
Tmin = 0.930, Tmax = 0.990l = −10→10
6055 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.115w = 1/[σ2(Fo2) + (0.0406P)2 + 0.9464P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3996 reflectionsΔρmax = 0.26 e Å3
362 parametersΔρmin = −0.35 e Å3
1 restraintAbsolute structure: Flack (1983), 1642 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.21 (12)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.40869 (16)0.34079 (7)0.07406 (13)0.0315 (3)
S20.29228 (16)0.56069 (6)0.66799 (14)0.0314 (3)
O10.6428 (5)0.40440 (18)0.4794 (4)0.0356 (9)
O20.2917 (5)0.38775 (19)−0.0206 (4)0.0366 (10)
O30.3351 (5)0.27849 (19)0.1139 (4)0.0419 (10)
O40.0634 (5)0.5048 (2)0.2569 (4)0.0380 (10)
O50.3689 (5)0.62390 (18)0.6366 (4)0.0396 (9)
O60.4061 (5)0.51239 (18)0.7608 (4)0.0370 (9)
F10.5315 (5)0.62712 (18)0.1306 (4)0.0595 (10)
F20.1460 (5)0.27594 (17)0.5845 (4)0.0573 (10)
C10.5062 (6)0.3838 (3)0.2392 (5)0.0292 (12)
C20.5405 (6)0.4548 (3)0.2512 (5)0.0277 (12)
C30.5098 (7)0.5105 (3)0.1556 (6)0.0326 (13)
H30.45600.50630.05370.039*
C40.5630 (8)0.5711 (3)0.2194 (6)0.0409 (14)
C50.6451 (8)0.5809 (3)0.3707 (7)0.0438 (16)
H50.67730.62400.40720.053*
C60.6775 (7)0.5265 (3)0.4641 (7)0.0388 (14)
H60.73240.53110.56560.047*
C70.6260 (7)0.4647 (3)0.4027 (6)0.0323 (13)
C80.5701 (7)0.3559 (3)0.3777 (6)0.0321 (13)
C90.5796 (8)0.2868 (3)0.4372 (6)0.0403 (15)
H9A0.51290.28420.51830.048*
H9B0.70650.27470.47420.048*
H9C0.52570.25630.35820.048*
C100.5988 (7)0.3223 (3)−0.0108 (6)0.0301 (13)
C110.6510 (7)0.3687 (3)−0.1085 (6)0.0390 (14)
H110.58330.4080−0.13420.047*
C120.8080 (7)0.3549 (3)−0.1675 (6)0.0412 (15)
H120.84700.3854−0.23300.049*
C130.9051 (8)0.2966 (4)−0.1293 (7)0.0495 (17)
H131.01080.2881−0.16790.059*
C140.8482 (8)0.2507 (3)−0.0353 (7)0.0452 (15)
H140.91390.2109−0.01190.054*
C150.6935 (7)0.2634 (3)0.0255 (6)0.0394 (14)
H150.65440.23230.08980.047*
C160.1980 (6)0.5209 (3)0.4988 (5)0.0275 (11)
C170.1588 (7)0.4501 (3)0.4804 (6)0.0300 (12)
C180.1820 (7)0.3933 (3)0.5702 (6)0.0341 (14)
H180.23550.39520.67250.041*
C190.1217 (7)0.3339 (3)0.5001 (7)0.0366 (14)
C200.0419 (8)0.3273 (3)0.3496 (7)0.0431 (15)
H200.00510.28520.30940.052*
C210.0171 (7)0.3837 (3)0.2591 (6)0.0409 (14)
H21−0.03570.38120.15680.049*
C220.0738 (7)0.4434 (3)0.3272 (6)0.0320 (13)
C230.1387 (7)0.5516 (3)0.3642 (6)0.0327 (13)
C240.1323 (8)0.6216 (3)0.3081 (7)0.0478 (16)
H24A0.00600.63450.27110.057*
H24B0.19990.62470.22780.057*
H24C0.18670.65110.38900.057*
C250.0987 (7)0.5777 (3)0.7488 (6)0.0293 (13)
C260.0476 (7)0.5332 (3)0.8495 (6)0.0375 (14)
H260.11570.49410.87760.045*
C27−0.1081 (8)0.5478 (3)0.9085 (7)0.0490 (17)
H27−0.14350.51870.97860.059*
C28−0.2091 (8)0.6040 (3)0.8651 (7)0.0461 (17)
H28−0.31290.61310.90570.055*
C29−0.1597 (8)0.6481 (3)0.7610 (7)0.0434 (15)
H29−0.23050.68630.73100.052*
C30−0.0042 (7)0.6347 (3)0.7022 (6)0.0385 (13)
H300.03070.66370.63190.046*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0254 (7)0.0406 (8)0.0272 (7)−0.0029 (6)0.0021 (5)−0.0014 (6)
S20.0266 (7)0.0380 (8)0.0283 (7)−0.0013 (6)0.0019 (5)−0.0018 (6)
O10.039 (2)0.041 (3)0.025 (2)0.0029 (17)0.0014 (16)0.0001 (18)
O20.029 (2)0.046 (3)0.032 (2)0.0034 (18)−0.0032 (16)−0.0049 (19)
O30.041 (2)0.047 (3)0.037 (2)−0.0117 (18)0.0056 (18)0.0009 (19)
O40.040 (2)0.047 (3)0.027 (2)0.0071 (18)0.0053 (16)0.0018 (19)
O50.035 (2)0.039 (2)0.045 (2)−0.0052 (18)0.0084 (17)−0.0042 (19)
O60.030 (2)0.046 (2)0.033 (2)0.0040 (17)0.0001 (16)0.0034 (19)
F10.083 (3)0.043 (2)0.057 (2)0.0025 (19)0.0235 (19)0.0091 (18)
F20.083 (3)0.043 (2)0.047 (2)−0.0026 (18)0.0171 (19)0.0020 (17)
C10.019 (3)0.041 (4)0.025 (3)−0.002 (2)0.001 (2)−0.001 (2)
C20.020 (3)0.043 (4)0.020 (3)−0.001 (2)0.005 (2)−0.004 (2)
C30.032 (3)0.041 (4)0.025 (3)0.002 (2)0.006 (2)−0.001 (3)
C40.046 (3)0.037 (4)0.042 (3)0.004 (3)0.016 (3)0.005 (3)
C50.041 (3)0.046 (4)0.047 (4)−0.006 (3)0.015 (3)−0.012 (3)
C60.033 (3)0.053 (4)0.030 (3)−0.004 (3)0.006 (2)−0.014 (3)
C70.026 (3)0.046 (4)0.025 (3)0.002 (2)0.005 (2)−0.002 (3)
C80.026 (3)0.038 (4)0.032 (3)0.004 (2)0.006 (2)−0.001 (3)
C90.043 (4)0.047 (4)0.028 (3)−0.003 (3)0.001 (3)0.006 (3)
C100.030 (3)0.043 (4)0.016 (2)−0.002 (2)0.000 (2)−0.004 (2)
C110.035 (3)0.053 (4)0.027 (3)−0.004 (3)−0.001 (2)−0.002 (3)
C120.036 (3)0.071 (5)0.015 (3)−0.009 (3)0.002 (2)−0.001 (3)
C130.038 (4)0.074 (5)0.037 (4)0.004 (3)0.011 (3)−0.010 (3)
C140.042 (3)0.054 (4)0.036 (3)0.012 (3)−0.001 (3)−0.010 (3)
C150.036 (3)0.044 (4)0.038 (3)0.002 (3)0.006 (3)−0.011 (3)
C160.025 (3)0.034 (3)0.024 (3)0.003 (2)0.004 (2)0.003 (2)
C170.019 (3)0.040 (4)0.031 (3)0.003 (2)0.004 (2)0.001 (2)
C180.033 (3)0.041 (4)0.030 (3)−0.001 (2)0.008 (2)0.000 (3)
C190.033 (3)0.035 (4)0.042 (3)0.000 (3)0.010 (3)0.005 (3)
C200.038 (3)0.050 (4)0.040 (3)−0.009 (3)0.006 (3)−0.012 (3)
C210.039 (3)0.057 (4)0.026 (3)0.000 (3)0.005 (2)−0.011 (3)
C220.027 (3)0.045 (4)0.024 (3)0.002 (2)0.005 (2)−0.001 (3)
C230.030 (3)0.039 (4)0.031 (3)0.001 (2)0.012 (2)0.000 (3)
C240.054 (4)0.051 (4)0.040 (4)0.015 (3)0.013 (3)0.007 (3)
C250.023 (3)0.039 (4)0.024 (3)−0.002 (2)0.001 (2)−0.007 (3)
C260.027 (3)0.054 (4)0.029 (3)−0.003 (2)−0.001 (2)0.003 (3)
C270.036 (3)0.081 (5)0.031 (3)−0.004 (3)0.008 (3)0.004 (3)
C280.031 (3)0.077 (5)0.029 (3)−0.004 (3)0.002 (3)−0.023 (3)
C290.035 (3)0.043 (4)0.050 (4)0.009 (3)0.003 (3)−0.011 (3)
C300.043 (3)0.034 (3)0.041 (3)0.000 (3)0.013 (3)−0.001 (3)

Geometric parameters (Å, °)

S1—O31.424 (4)C12—C131.368 (8)
S1—O21.432 (4)C12—H120.9300
S1—C11.744 (5)C13—C141.365 (8)
S1—C101.764 (6)C13—H130.9300
S2—O51.426 (4)C14—C151.383 (8)
S2—O61.430 (4)C14—H140.9300
S2—C161.738 (5)C15—H150.9300
S2—C251.759 (5)C16—C231.352 (7)
O1—C81.364 (6)C16—C171.437 (7)
O1—C71.375 (6)C17—C181.378 (7)
O4—C221.369 (6)C17—C221.408 (7)
O4—C231.377 (6)C18—C191.369 (8)
F1—C41.363 (6)C18—H180.9300
F2—C191.371 (7)C19—C201.377 (8)
C1—C81.364 (7)C20—C211.375 (8)
C1—C21.431 (7)C20—H200.9300
C2—C31.392 (7)C21—C221.361 (8)
C2—C71.402 (7)C21—H210.9300
C3—C41.357 (8)C23—C241.474 (7)
C3—H30.9300C24—H24A0.9600
C4—C51.393 (8)C24—H24B0.9600
C5—C61.361 (8)C24—H24C0.9600
C5—H50.9300C25—C261.372 (7)
C6—C71.368 (8)C25—C301.381 (7)
C6—H60.9300C26—C271.389 (8)
C8—C91.469 (8)C26—H260.9300
C9—H9A0.9600C27—C281.356 (8)
C9—H9B0.9600C27—H270.9300
C9—H9C0.9600C28—C291.383 (8)
C10—C151.368 (7)C28—H280.9300
C10—C111.380 (8)C29—C301.381 (8)
C11—C121.394 (8)C29—H290.9300
C11—H110.9300C30—H300.9300
O3—S1—O2120.0 (2)C12—C13—H13119.7
O3—S1—C1108.8 (2)C13—C14—C15120.3 (6)
O2—S1—C1106.9 (2)C13—C14—H14119.8
O3—S1—C10107.7 (2)C15—C14—H14119.8
O2—S1—C10108.3 (2)C10—C15—C14118.8 (6)
C1—S1—C10104.1 (2)C10—C15—H15120.6
O5—S2—O6119.7 (2)C14—C15—H15120.6
O5—S2—C16109.3 (2)C23—C16—C17108.3 (4)
O6—S2—C16107.3 (2)C23—C16—S2126.0 (4)
O5—S2—C25107.5 (2)C17—C16—S2125.6 (4)
O6—S2—C25108.4 (2)C18—C17—C22118.7 (5)
C16—S2—C25103.5 (2)C18—C17—C16137.1 (5)
C8—O1—C7106.9 (4)C22—C17—C16104.3 (4)
C22—O4—C23107.2 (4)C19—C18—C17116.1 (5)
C8—C1—C2107.8 (4)C19—C18—H18122.0
C8—C1—S1126.5 (4)C17—C18—H18122.0
C2—C1—S1125.7 (4)C18—C19—F2118.0 (5)
C3—C2—C7118.7 (5)C18—C19—C20125.1 (6)
C3—C2—C1136.7 (5)F2—C19—C20116.9 (5)
C7—C2—C1104.5 (4)C21—C20—C19119.3 (6)
C4—C3—C2116.2 (5)C21—C20—H20120.3
C4—C3—H3121.9C19—C20—H20120.3
C2—C3—H3121.9C22—C21—C20116.4 (5)
C3—C4—F1118.1 (5)C22—C21—H21121.8
C3—C4—C5125.0 (6)C20—C21—H21121.8
F1—C4—C5116.9 (6)C21—C22—O4125.5 (5)
C6—C5—C4119.1 (6)C21—C22—C17124.4 (5)
C6—C5—H5120.5O4—C22—C17110.1 (5)
C4—C5—H5120.5C16—C23—O4110.0 (4)
C5—C6—C7117.2 (5)C16—C23—C24135.6 (5)
C5—C6—H6121.4O4—C23—C24114.3 (5)
C7—C6—H6121.4C23—C24—H24A109.5
C6—C7—O1125.8 (5)C23—C24—H24B109.5
C6—C7—C2123.8 (5)H24A—C24—H24B109.5
O1—C7—C2110.4 (5)C23—C24—H24C109.5
C1—C8—O1110.5 (5)H24A—C24—H24C109.5
C1—C8—C9134.2 (5)H24B—C24—H24C109.5
O1—C8—C9115.3 (4)C26—C25—C30121.5 (5)
C8—C9—H9A109.5C26—C25—S2120.2 (4)
C8—C9—H9B109.5C30—C25—S2118.2 (4)
H9A—C9—H9B109.5C25—C26—C27118.4 (5)
C8—C9—H9C109.5C25—C26—H26120.8
H9A—C9—H9C109.5C27—C26—H26120.8
H9B—C9—H9C109.5C28—C27—C26120.6 (6)
C15—C10—C11121.9 (5)C28—C27—H27119.7
C15—C10—S1119.1 (4)C26—C27—H27119.7
C11—C10—S1119.0 (4)C27—C28—C29120.9 (6)
C10—C11—C12118.1 (6)C27—C28—H28119.6
C10—C11—H11120.9C29—C28—H28119.6
C12—C11—H11120.9C30—C29—C28119.3 (6)
C13—C12—C11120.1 (6)C30—C29—H29120.4
C13—C12—H12119.9C28—C29—H29120.4
C11—C12—H12119.9C25—C30—C29119.3 (5)
C14—C13—C12120.7 (6)C25—C30—H30120.4
C14—C13—H13119.7C29—C30—H30120.4
O3—S1—C1—C824.1 (5)O5—S2—C16—C23−24.0 (5)
O2—S1—C1—C8155.0 (4)O6—S2—C16—C23−155.2 (4)
C10—S1—C1—C8−90.6 (5)C25—S2—C16—C2390.3 (5)
O3—S1—C1—C2−158.9 (4)O5—S2—C16—C17160.2 (4)
O2—S1—C1—C2−28.0 (5)O6—S2—C16—C1729.1 (5)
C10—S1—C1—C286.5 (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—C32.8 (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—C22176.3 (4)
C7—C2—C3—C4−1.4 (7)C22—C17—C18—C191.1 (7)
C1—C2—C3—C4178.1 (5)C16—C17—C18—C19−179.7 (5)
C2—C3—C4—F1−178.5 (4)C17—C18—C19—F2178.5 (4)
C2—C3—C4—C50.3 (8)C17—C18—C19—C200.2 (8)
C3—C4—C5—C60.5 (9)C18—C19—C20—C21−0.5 (9)
F1—C4—C5—C6179.3 (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—O4179.2 (5)
C5—C6—C7—C2−0.9 (8)C20—C21—C22—C171.7 (8)
C8—O1—C7—C6178.1 (5)C23—O4—C22—C21−178.6 (5)
C8—O1—C7—C20.5 (5)C23—O4—C22—C17−0.9 (5)
C3—C2—C7—C61.8 (7)C18—C17—C22—C21−2.1 (8)
C1—C2—C7—C6−177.9 (5)C16—C17—C22—C21178.4 (5)
C3—C2—C7—O1179.4 (4)C18—C17—C22—O4−179.9 (4)
C1—C2—C7—O1−0.3 (5)C16—C17—C22—O40.6 (5)
C2—C1—C8—O10.4 (5)C17—C16—C23—O4−0.5 (5)
S1—C1—C8—O1177.9 (3)S2—C16—C23—O4−176.8 (3)
C2—C1—C8—C9−178.3 (5)C17—C16—C23—C24177.9 (5)
S1—C1—C8—C9−0.8 (8)S2—C16—C23—C241.5 (9)
C7—O1—C8—C1−0.6 (5)C22—O4—C23—C160.9 (5)
C7—O1—C8—C9178.4 (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—C1589.3 (5)C16—S2—C25—C2693.9 (4)
O3—S1—C10—C11155.8 (4)O5—S2—C25—C3032.8 (5)
O2—S1—C10—C1124.6 (5)O6—S2—C25—C30163.5 (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—C12176.3 (4)S2—C25—C26—C27−178.8 (4)
C10—C11—C12—C130.5 (8)C25—C26—C27—C281.3 (8)
C11—C12—C13—C141.0 (9)C26—C27—C28—C290.1 (9)
C12—C13—C14—C15−1.4 (9)C27—C28—C29—C30−0.7 (9)
C11—C10—C15—C141.4 (8)C26—C25—C30—C291.6 (8)
S1—C10—C15—C14−176.7 (4)S2—C25—C30—C29178.3 (4)
C13—C14—C15—C100.2 (8)C28—C29—C30—C25−0.1 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O6i0.932.603.494 (6)162
C26—H26···O2ii0.932.553.479 (7)174

Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2699).

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