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5-Cyclo-hexyl-2-(3-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzofuran.
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PMID:  22590006     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
In the title compound, C(21)H(21)FO(2)S, the cyclo-hexyl ring adopts a chair conformation. The 3-fluoro-phenyl ring makes a dihedral angle of 38.38 (6)° with the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds.
Authors:
Hong Dae Choi; Pil Ja Seo; Uk Lee
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Publication Detail:
Type:  Journal Article     Date:  2012-03-03
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  68     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2012 Apr 
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Created Date:  2012-05-16     Completed Date:  -     Revised Date:  -    
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Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  United States    
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Languages:  eng     Pagination:  o944     Citation Subset:  -    
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Journal Information
Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (iso-abbrev): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
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A full version of this article is available from Crystallography Journals Online.© Choi et al. 2012
open-access:
Received Day: 20 Month: 2 Year: 2012
Accepted Day: 24 Month: 2 Year: 2012
collection publication date: Day: 01 Month: 4 Year: 2012
Electronic publication date: Day: 03 Month: 3 Year: 2012
pmc-release publication date: Day: 03 Month: 3 Year: 2012
Volume: 68 Issue: Pt 4
First Page: o944 Last Page: o944
ID: 3343925
PubMed Id: 22590006
Publisher Id: bh2416
DOI: 10.1107/S1600536812008343
Coden: ACSEBH
Publisher Item Identifier: S1600536812008343

5-Cyclo­hexyl-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran Alternate Title:C21H21FO2S
Hong Dae Choia
Pil Ja Seoa
Uk Leeb*
aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea
bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
Correspondence: Correspondence e-mail: uklee@pknu.ac.kr

Related literature  

For background information and the crystal structures of related compounds, see: Choi et al. (2011a,b).[Chemical Structure ID: scheme1]


Experimental  
Crystal data  

  • C21H21FO2S
  • Mr = 356.44
  • Orthorhombic,
  • a = 12.7767 (10) Å
  • b = 13.0764 (10) Å
  • c = 10.7711 (8) Å
  • V = 1799.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 173 K
  • 0.34 × 0.24 × 0.20 mm

Data collection  

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.935, Tmax = 0.961
  • 17893 measured reflections
  • 4503 independent reflections
  • 4036 reflections with I > 2σ(I)
  • Rint = 0.058

Refinement  

  • R[F2 > 2σ(F2)] = 0.041
  • wR(F2) = 0.096
  • S = 1.03
  • 4503 reflections
  • 227 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983), 2131 Friedel pairs
  • Flack parameter: −0.07 (7)

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.


Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008343/bh2416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008343/bh2416Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008343/bh2416Isup3.cml

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


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2416).

This work was supported by a Dongeui University Foundation grant (2011).

supplementary crystallographic information
Comment

As a part of our ongoing study of 5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives containing either 2-phenyl (Choi et al., 2011a) or 2-(4-fluorophenyl) (Choi et al., 2011b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofurn fragment is 38.38 (6)°. The crystal packing is stabilized by weak intermolecular C–H···O hydrogen bonds (Table 1).

Experimental

77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4 h., the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 443-444 K; Rf = 0.55 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl, 1.0 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) =1.2Ueq(C) for aryl, methine, and methylene, and 1.5Ueq(C) for methyl H atoms.

Figures
Crystal data
Data collection
Refinement
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, º)
Hydrogen-bond geometry (Å, º)

Symmetry code: (i) −x+1, −y, z−1/2.


References
Brandenburg, K. (1998). DIAMOND Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2, SADABS and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o281.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.
Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Figures

[Figure ID: Fap1]
Fig. 1. 

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.



Tables
[TableWrap ID: d1e137]
C21H21FO2S Dx = 1.316 Mg m3
Mr = 356.44 Melting point: 443 K
Orthorhombic, Pna21 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n Cell parameters from 4473 reflections
a = 12.7767 (10) Å θ = 2.5–28.1°
b = 13.0764 (10) Å µ = 0.20 mm1
c = 10.7711 (8) Å T = 173 K
V = 1799.6 (2) Å3 Block, colourless
Z = 4 0.34 × 0.24 × 0.20 mm
F(000) = 752

[TableWrap ID: d1e264]
Bruker SMART APEXII CCD diffractometer 4503 independent reflections
Radiation source: rotating anode 4036 reflections with I > 2σ(I)
Graphite multilayer monochromator Rint = 0.058
Detector resolution: 10.0 pixels mm-1 θmax = 28.4°, θmin = 2.2°
φ and ω scans h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2009) k = −17→16
Tmin = 0.935, Tmax = 0.961 l = −14→14
17893 measured reflections

[TableWrap ID: d1e387]
Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041 H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0426P)2 + 0.2167P] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max < 0.001
4503 reflections Δρmax = 0.33 e Å3
227 parameters Δρmin = −0.25 e Å3
1 restraint Absolute structure: Flack (1983), 2131 Friedel pairs
0 constraints Flack parameter: −0.07 (7)
Primary atom site location: structure-invariant direct methods

[TableWrap ID: d1e558]
x y z Uiso*/Ueq
S1 0.56575 (3) 0.02701 (3) 0.35040 (5) 0.02691 (11)
F1 0.77633 (15) 0.11534 (12) −0.03264 (18) 0.0792 (6)
O1 0.46206 (10) 0.30803 (10) 0.29361 (13) 0.0277 (3)
O2 0.56405 (11) −0.00184 (12) 0.48474 (14) 0.0390 (4)
C1 0.49571 (12) 0.14257 (13) 0.33717 (18) 0.0234 (3)
C2 0.40393 (13) 0.17197 (14) 0.40656 (17) 0.0231 (3)
C3 0.33673 (13) 0.12486 (14) 0.49109 (16) 0.0254 (4)
H3 0.3475 0.0555 0.5143 0.031*
C4 0.25446 (14) 0.17975 (15) 0.54083 (17) 0.0257 (4)
C5 0.24014 (14) 0.28249 (15) 0.5060 (2) 0.0296 (4)
H5 0.1833 0.3196 0.5408 0.036*
C6 0.30589 (14) 0.33145 (15) 0.42275 (19) 0.0287 (4)
H6 0.2957 0.4009 0.3997 0.034*
C7 0.38672 (13) 0.27399 (14) 0.37531 (16) 0.0260 (4)
C8 0.52756 (14) 0.22666 (14) 0.27291 (16) 0.0256 (4)
C9 0.17818 (14) 0.12816 (16) 0.62864 (17) 0.0287 (4)
H9 0.2064 0.0585 0.6469 0.034*
C10 0.16664 (19) 0.1834 (2) 0.7521 (2) 0.0443 (5)
H10A 0.1439 0.2547 0.7367 0.053*
H10B 0.2354 0.1858 0.7943 0.053*
C11 0.08727 (19) 0.1306 (2) 0.8365 (2) 0.0554 (7)
H11A 0.1153 0.0634 0.8625 0.067*
H11B 0.0767 0.1725 0.9121 0.067*
C12 −0.01698 (19) 0.1153 (2) 0.7722 (3) 0.0573 (8)
H12A −0.0642 0.0761 0.8273 0.069*
H12B −0.0495 0.1827 0.7564 0.069*
C13 −0.00474 (18) 0.0591 (2) 0.6512 (3) 0.0494 (6)
H13A −0.0736 0.0540 0.6095 0.059*
H13B 0.0206 −0.0112 0.6676 0.059*
C14 0.07219 (16) 0.1139 (2) 0.5661 (2) 0.0405 (5)
H14A 0.0434 0.1816 0.5431 0.049*
H14B 0.0813 0.0737 0.4890 0.049*
C15 0.61838 (13) 0.24653 (16) 0.19341 (17) 0.0269 (4)
C16 0.65392 (17) 0.17134 (18) 0.1135 (2) 0.0389 (5)
H16 0.6172 0.1086 0.1051 0.047*
C17 0.74380 (18) 0.18950 (19) 0.0462 (2) 0.0457 (6)
C18 0.79812 (17) 0.27964 (19) 0.0536 (2) 0.0421 (5)
H18 0.8604 0.2896 0.0069 0.051*
C19 0.76030 (16) 0.35559 (19) 0.1303 (2) 0.0376 (5)
H19 0.7957 0.4194 0.1349 0.045*
C20 0.67083 (14) 0.33938 (16) 0.20081 (19) 0.0306 (4)
H20 0.6455 0.3917 0.2541 0.037*
C21 0.47422 (18) −0.05631 (16) 0.2771 (2) 0.0378 (5)
H21A 0.5009 −0.1266 0.2794 0.057*
H21B 0.4644 −0.0352 0.1905 0.057*
H21C 0.4071 −0.0530 0.3209 0.057*

[TableWrap ID: d1e1174]
U11 U22 U33 U12 U13 U23
S1 0.02477 (19) 0.0252 (2) 0.0307 (2) 0.00363 (16) 0.00124 (19) 0.0016 (2)
F1 0.0930 (12) 0.0564 (10) 0.0883 (13) 0.0007 (9) 0.0641 (10) −0.0086 (9)
O1 0.0257 (6) 0.0243 (7) 0.0332 (7) −0.0006 (5) 0.0024 (5) 0.0051 (6)
O2 0.0457 (9) 0.0377 (8) 0.0335 (8) 0.0094 (7) −0.0076 (7) 0.0065 (7)
C1 0.0219 (7) 0.0237 (8) 0.0246 (9) −0.0008 (6) 0.0011 (7) 0.0004 (8)
C2 0.0207 (7) 0.0243 (9) 0.0243 (8) 0.0011 (7) −0.0022 (6) 0.0010 (7)
C3 0.0255 (8) 0.0236 (9) 0.0272 (9) 0.0014 (7) 0.0001 (7) 0.0023 (7)
C4 0.0246 (9) 0.0267 (10) 0.0256 (9) 0.0020 (7) 0.0008 (7) 0.0007 (7)
C5 0.0248 (9) 0.0291 (10) 0.0350 (10) 0.0042 (7) 0.0020 (7) −0.0021 (8)
C6 0.0279 (9) 0.0232 (9) 0.0352 (10) 0.0026 (7) −0.0013 (8) 0.0013 (8)
C7 0.0219 (8) 0.0262 (9) 0.0301 (10) −0.0030 (7) −0.0022 (7) 0.0023 (7)
C8 0.0244 (8) 0.0264 (10) 0.0260 (9) 0.0005 (7) −0.0019 (7) 0.0011 (7)
C9 0.0284 (9) 0.0306 (10) 0.0271 (9) 0.0055 (7) 0.0042 (7) 0.0033 (8)
C10 0.0440 (12) 0.0575 (15) 0.0315 (11) −0.0056 (11) 0.0084 (9) −0.0057 (10)
C11 0.0643 (15) 0.0647 (17) 0.0373 (13) −0.0022 (12) 0.0242 (12) −0.0026 (13)
C12 0.0434 (13) 0.0520 (15) 0.077 (2) 0.0069 (12) 0.0309 (13) 0.0186 (14)
C13 0.0353 (11) 0.0559 (16) 0.0571 (15) −0.0109 (11) 0.0033 (10) 0.0208 (12)
C14 0.0383 (12) 0.0457 (14) 0.0376 (11) −0.0115 (10) −0.0014 (9) 0.0124 (10)
C15 0.0250 (8) 0.0297 (10) 0.0261 (9) 0.0002 (7) 0.0008 (7) 0.0066 (7)
C16 0.0445 (12) 0.0335 (12) 0.0387 (12) −0.0035 (9) 0.0140 (9) 0.0040 (9)
C17 0.0474 (13) 0.0440 (14) 0.0457 (13) 0.0073 (11) 0.0228 (11) 0.0087 (11)
C18 0.0297 (10) 0.0564 (15) 0.0402 (12) 0.0000 (10) 0.0101 (9) 0.0163 (11)
C19 0.0295 (10) 0.0448 (13) 0.0386 (11) −0.0125 (9) −0.0027 (9) 0.0095 (10)
C20 0.0289 (9) 0.0315 (11) 0.0312 (10) −0.0024 (8) −0.0044 (8) 0.0049 (8)
C21 0.0447 (12) 0.0281 (10) 0.0406 (12) −0.0025 (9) −0.0070 (9) −0.0039 (9)

[TableWrap ID: d1e1645]
S1—O2 1.4954 (15) C11—C12 1.515 (4)
S1—C1 1.7620 (17) C11—H11A 0.9900
S1—C21 1.783 (2) C11—H11B 0.9900
F1—C17 1.355 (3) C12—C13 1.505 (4)
O1—C8 1.372 (2) C12—H12A 0.9900
O1—C7 1.378 (2) C12—H12B 0.9900
C1—C8 1.361 (3) C13—C14 1.523 (3)
C1—C2 1.443 (2) C13—H13A 0.9900
C2—C7 1.393 (3) C13—H13B 0.9900
C2—C3 1.395 (2) C14—H14A 0.9900
C3—C4 1.381 (2) C14—H14B 0.9900
C3—H3 0.9500 C15—C16 1.383 (3)
C4—C5 1.407 (3) C15—C20 1.389 (3)
C4—C9 1.516 (3) C16—C17 1.378 (3)
C5—C6 1.385 (3) C16—H16 0.9500
C5—H5 0.9500 C17—C18 1.370 (3)
C6—C7 1.376 (3) C18—C19 1.379 (3)
C6—H6 0.9500 C18—H18 0.9500
C8—C15 1.465 (2) C19—C20 1.389 (3)
C9—C10 1.520 (3) C19—H19 0.9500
C9—C14 1.524 (3) C20—H20 0.9500
C9—H9 1.0000 C21—H21A 0.9800
C10—C11 1.527 (3) C21—H21B 0.9800
C10—H10A 0.9900 C21—H21C 0.9800
C10—H10B 0.9900
O2—S1—C1 106.69 (9) C10—C11—H11B 109.3
O2—S1—C21 105.37 (10) H11A—C11—H11B 107.9
C1—S1—C21 98.93 (9) C13—C12—C11 111.69 (19)
C8—O1—C7 106.23 (14) C13—C12—H12A 109.3
C8—C1—C2 106.92 (15) C11—C12—H12A 109.3
C8—C1—S1 125.59 (13) C13—C12—H12B 109.3
C2—C1—S1 126.83 (13) C11—C12—H12B 109.3
C7—C2—C3 118.91 (16) H12A—C12—H12B 107.9
C7—C2—C1 104.97 (15) C12—C13—C14 111.0 (2)
C3—C2—C1 136.11 (17) C12—C13—H13A 109.4
C4—C3—C2 119.48 (17) C14—C13—H13A 109.4
C4—C3—H3 120.3 C12—C13—H13B 109.4
C2—C3—H3 120.3 C14—C13—H13B 109.4
C3—C4—C5 119.46 (17) H13A—C13—H13B 108.0
C3—C4—C9 120.00 (17) C13—C14—C9 111.42 (18)
C5—C4—C9 120.51 (16) C13—C14—H14A 109.3
C6—C5—C4 122.35 (17) C9—C14—H14A 109.3
C6—C5—H5 118.8 C13—C14—H14B 109.3
C4—C5—H5 118.8 C9—C14—H14B 109.3
C7—C6—C5 116.31 (17) H14A—C14—H14B 108.0
C7—C6—H6 121.8 C16—C15—C20 119.90 (18)
C5—C6—H6 121.8 C16—C15—C8 119.84 (18)
C6—C7—O1 125.82 (17) C20—C15—C8 120.22 (18)
C6—C7—C2 123.48 (17) C17—C16—C15 118.6 (2)
O1—C7—C2 110.69 (15) C17—C16—H16 120.7
C1—C8—O1 111.19 (15) C15—C16—H16 120.7
C1—C8—C15 132.60 (17) F1—C17—C18 119.79 (19)
O1—C8—C15 116.14 (16) F1—C17—C16 117.5 (2)
C4—C9—C10 113.34 (18) C18—C17—C16 122.7 (2)
C4—C9—C14 110.48 (16) C17—C18—C19 118.5 (2)
C10—C9—C14 111.02 (18) C17—C18—H18 120.8
C4—C9—H9 107.2 C19—C18—H18 120.8
C10—C9—H9 107.2 C18—C19—C20 120.4 (2)
C14—C9—H9 107.2 C18—C19—H19 119.8
C9—C10—C11 111.7 (2) C20—C19—H19 119.8
C9—C10—H10A 109.3 C19—C20—C15 119.9 (2)
C11—C10—H10A 109.3 C19—C20—H20 120.0
C9—C10—H10B 109.3 C15—C20—H20 120.0
C11—C10—H10B 109.3 S1—C21—H21A 109.5
H10A—C10—H10B 107.9 S1—C21—H21B 109.5
C12—C11—C10 111.8 (2) H21A—C21—H21B 109.5
C12—C11—H11A 109.3 S1—C21—H21C 109.5
C10—C11—H11A 109.3 H21A—C21—H21C 109.5
C12—C11—H11B 109.3 H21B—C21—H21C 109.5
O2—S1—C1—C8 133.15 (16) C7—O1—C8—C15 −176.61 (15)
C21—S1—C1—C8 −117.75 (17) C3—C4—C9—C10 125.5 (2)
O2—S1—C1—C2 −36.29 (18) C5—C4—C9—C10 −56.7 (2)
C21—S1—C1—C2 72.81 (18) C3—C4—C9—C14 −109.2 (2)
C8—C1—C2—C7 1.11 (19) C5—C4—C9—C14 68.6 (2)
S1—C1—C2—C7 172.15 (13) C4—C9—C10—C11 178.61 (19)
C8—C1—C2—C3 −177.8 (2) C14—C9—C10—C11 53.6 (3)
S1—C1—C2—C3 −6.8 (3) C9—C10—C11—C12 −53.3 (3)
C7—C2—C3—C4 0.6 (3) C10—C11—C12—C13 54.5 (3)
C1—C2—C3—C4 179.4 (2) C11—C12—C13—C14 −55.9 (3)
C2—C3—C4—C5 −0.4 (3) C12—C13—C14—C9 56.4 (3)
C2—C3—C4—C9 177.44 (16) C4—C9—C14—C13 178.2 (2)
C3—C4—C5—C6 0.0 (3) C10—C9—C14—C13 −55.2 (3)
C9—C4—C5—C6 −177.75 (18) C1—C8—C15—C16 39.0 (3)
C4—C5—C6—C7 0.0 (3) O1—C8—C15—C16 −144.42 (19)
C5—C6—C7—O1 −178.59 (17) C1—C8—C15—C20 −139.0 (2)
C5—C6—C7—C2 0.2 (3) O1—C8—C15—C20 37.6 (2)
C8—O1—C7—C6 178.97 (17) C20—C15—C16—C17 2.5 (3)
C8—O1—C7—C2 0.04 (19) C8—C15—C16—C17 −175.5 (2)
C3—C2—C7—C6 −0.5 (3) C15—C16—C17—F1 −179.1 (2)
C1—C2—C7—C6 −179.67 (17) C15—C16—C17—C18 −1.3 (4)
C3—C2—C7—O1 178.43 (15) F1—C17—C18—C19 176.9 (2)
C1—C2—C7—O1 −0.7 (2) C16—C17—C18—C19 −0.9 (4)
C2—C1—C8—O1 −1.1 (2) C17—C18—C19—C20 1.8 (3)
S1—C1—C8—O1 −172.33 (13) C18—C19—C20—C15 −0.6 (3)
C2—C1—C8—C15 175.59 (19) C16—C15—C20—C19 −1.6 (3)
S1—C1—C8—C15 4.4 (3) C8—C15—C20—C19 176.39 (18)
C7—O1—C8—C1 0.71 (19)

[TableWrap ID: d1e2602]
D—H···A D—H H···A D···A D—H···A
C21—H21B···O2i 0.98 2.30 3.276 (3) 176


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