organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

5-Cyclo­hexyl-2-(4-fluoro­phen­yl)-3-phenyl­sulfinyl-1-benzo­furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 5 August 2013; accepted 12 August 2013; online 21 August 2013)

The asymmetric unit of the title compound, C26H23FO2S, contains two independent mol­ecules (A and B), in both of which the cyclo­hexyl ring adopts a chair conformation. The benzo­furan ring systems, the 4-fluoro­phenyl and phenyl rings are essentially planar, with r.m.s. deviations of 0.008 (1), 0.002 (1) and 0.003 (1) Å, respectively, for mol­ecule A, and 0.016 (1), 0.004 (1) and 0.002 (1) Å, respectively, for mol­ecule B. The dihedral angles between the benzo­furan ring system and the pendant 4-fluoro­phenyl and phenyl rings are 12.3 (7) and 85.42 (4)°, respectively, for mol­ecule A, and 39.67 (6) and 72.17 (4)°, respectively, for mol­ecule B. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions, resulting in a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o498.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1237.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.]).

[Scheme 1]

Experimental

Crystal data
  • C26H23FO2S

  • Mr = 418.50

  • Triclinic, [P \overline 1]

  • a = 9.1536 (2) Å

  • b = 12.6562 (2) Å

  • c = 19.3939 (4) Å

  • α = 84.674 (1)°

  • β = 79.667 (1)°

  • γ = 72.405 (1)°

  • V = 2105.15 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 173 K

  • 0.38 × 0.27 × 0.25 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.702, Tmax = 0.746

  • 36372 measured reflections

  • 9183 independent reflections

  • 7799 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.100

  • S = 1.03

  • 9183 reflections

  • 541 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C41–C46 4-fluoro­phenyl ring and the C2–C7 benzene ring, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10B⋯O2i 0.99 2.47 3.384 (2) 153
C22—H22⋯O2i 0.95 2.42 3.2365 (19) 144
C19—H19⋯O4ii 0.95 2.44 3.3442 (19) 159
C40—H40BCg1iii 0.99 2.84 3.763 (2) 155
C45—H45⋯Cg2 0.95 2.82 3.602 (2) 140
C50—H50⋯Cg1iv 0.95 2.80 3.619 (2) 144
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) -x, -y+2, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of our continuing study of 2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran derivatives containing chloro (Choi et al., 2011), bromo (Seo et al., 2011), and iodo (Choi et al., 2012) groups in 5-position, we report here the crystal structure of the title compound which crystallizes with two independent molecules, A & B, in the asymmetric unit.

In the title compound (Fig. 1), the cyclohexyl ring of both molecules adopts a chair conformation. The benzofuran ring system is essentially planar, with a mean deviation of 0.008 (1) and 0.016 (1) Å, for A and B, respectively, from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl and phenyl rings are essentially planar, with mean deviations of 0.002 (1) and 0.003 (1) Å for molecule A, and 0.004 (1) and 0.002 (1) Å for molecule B, respectively, from the least-squares plane defined by the six constituent atoms. The dihedral angles formed by the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 12.31 (7) and 85.42 (4)° in molecule A, and 39.67 (6) and 72.17 (4)° in molecule B, respectively. In the crystal packing, molecules are connected by weak C—H···O hydrogen bonds (Fig. 2 and Table 2) and C—H···π interactions (Fig. 3 and Table 2, Cg1 and Cg2 are the centroids of the C41–C46 4-fluorophenyl ring and the C2–C7 benzene ring, respectively), resulting in a three-dimensional network.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011, 2012); Seo et al. (2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(4-fluorophenyl)-3-phenylsulfanyl-1-benzofuran (322 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 63%, m.p. 403–404 K; Rf = 0.78 (hexane–ethyl acetate, 2:1 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 top

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å for aryl, 1.00 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 The positions of methyl hydrogens were optimized rotationally.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] 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 small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z; (ii) - x, - y + 1, - z + 1.]
[Figure 3] Fig. 3. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (iii) - x, 2- y + 2, - z + 1; (iv) x, y, z; (v) - x + 1, - y + 1, - z + 1.]
5-Cyclohexyl-2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran top
Crystal data top
C26H23FO2SZ = 4
Mr = 418.50F(000) = 880
Triclinic, P1Dx = 1.320 Mg m3
Hall symbol: -P 1Melting point: 403 K
a = 9.1536 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6562 (2) ÅCell parameters from 9956 reflections
c = 19.3939 (4) Åθ = 2.5–28.3°
α = 84.674 (1)°µ = 0.18 mm1
β = 79.667 (1)°T = 173 K
γ = 72.405 (1)°Block, colourless
V = 2105.15 (7) Å30.38 × 0.27 × 0.25 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
9183 independent reflections
Radiation source: rotating anode7799 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.1°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1616
Tmin = 0.702, Tmax = 0.746l = 2424
36372 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.100H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0483P)2 + 0.7052P]
where P = (Fo2 + 2Fc2)/3
9183 reflections(Δ/σ)max = 0.001
541 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C26H23FO2Sγ = 72.405 (1)°
Mr = 418.50V = 2105.15 (7) Å3
Triclinic, P1Z = 4
a = 9.1536 (2) ÅMo Kα radiation
b = 12.6562 (2) ŵ = 0.18 mm1
c = 19.3939 (4) ÅT = 173 K
α = 84.674 (1)°0.38 × 0.27 × 0.25 mm
β = 79.667 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
9183 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
7799 reflections with I > 2σ(I)
Tmin = 0.702, Tmax = 0.746Rint = 0.028
36372 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.03Δρmax = 0.34 e Å3
9183 reflectionsΔρmin = 0.35 e Å3
541 parameters
Special details top

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) top
xyzUiso*/Ueq
S10.51941 (4)0.39671 (3)0.142600 (18)0.02863 (9)
F10.45285 (11)0.11763 (8)0.46866 (5)0.0447 (2)
O10.18092 (11)0.54650 (8)0.29154 (5)0.0306 (2)
O20.46030 (13)0.40426 (9)0.07538 (6)0.0395 (3)
C10.36986 (15)0.48459 (11)0.20035 (7)0.0267 (3)
C20.27527 (15)0.59273 (11)0.17968 (7)0.0268 (3)
C30.27759 (16)0.66238 (11)0.11966 (7)0.0282 (3)
H30.35440.64020.07960.034*
C40.16491 (16)0.76520 (11)0.11967 (8)0.0291 (3)
C50.05089 (17)0.79447 (12)0.17950 (8)0.0335 (3)
H50.02620.86420.17870.040*
C60.04609 (17)0.72625 (12)0.23941 (8)0.0336 (3)
H60.03180.74710.27930.040*
C70.16126 (16)0.62613 (11)0.23777 (7)0.0287 (3)
C80.30912 (15)0.46032 (11)0.26738 (7)0.0277 (3)
C90.16859 (16)0.84687 (11)0.05791 (8)0.0305 (3)
H90.06130.89890.05980.037*
C100.2120 (2)0.79323 (14)0.01261 (9)0.0507 (5)
H10A0.13450.75530.01750.061*
H10B0.31430.73650.01460.061*
C110.2190 (3)0.87806 (15)0.07329 (9)0.0570 (5)
H11A0.25600.83920.11800.068*
H11B0.11340.92870.07520.068*
C120.3265 (3)0.9450 (2)0.06525 (12)0.0708 (7)
H12A0.43410.89550.06830.085*
H12B0.32401.00200.10400.085*
C130.2791 (3)1.00101 (18)0.00423 (11)0.0609 (5)
H13A0.17511.05550.00560.073*
H13B0.35361.04160.00900.073*
C140.2753 (2)0.91600 (15)0.06525 (10)0.0477 (4)
H14A0.38160.86640.06680.057*
H14B0.23840.95490.10990.057*
C150.34829 (16)0.36826 (11)0.31857 (7)0.0283 (3)
C160.49049 (16)0.28528 (12)0.30941 (8)0.0313 (3)
H160.56400.28730.26840.038*
C170.52526 (17)0.20011 (12)0.35957 (8)0.0337 (3)
H170.62160.14340.35320.040*
C180.41714 (18)0.19941 (12)0.41886 (8)0.0335 (3)
C190.27566 (19)0.27905 (13)0.43010 (8)0.0377 (3)
H190.20290.27600.47130.045*
C200.24248 (18)0.36376 (13)0.37965 (8)0.0347 (3)
H200.14580.42000.38670.042*
C210.65459 (16)0.47748 (11)0.13046 (7)0.0298 (3)
C220.70074 (19)0.51549 (14)0.06361 (8)0.0397 (3)
H220.65640.50440.02520.048*
C230.8142 (2)0.57062 (16)0.05396 (11)0.0545 (5)
H230.84680.59850.00850.065*
C240.8794 (2)0.58498 (17)0.10984 (12)0.0577 (5)
H240.95770.62170.10250.069*
C250.8316 (2)0.54631 (17)0.17639 (11)0.0526 (5)
H250.87640.55710.21480.063*
C260.71881 (18)0.49197 (14)0.18720 (8)0.0391 (3)
H260.68570.46490.23280.047*
S20.20524 (4)0.67170 (3)0.453110 (18)0.03051 (9)
F20.64505 (14)0.83089 (9)0.17479 (5)0.0610 (3)
O30.25741 (11)0.96430 (8)0.47026 (5)0.0311 (2)
O40.04149 (12)0.67966 (9)0.44733 (6)0.0395 (3)
C270.20969 (16)0.79849 (12)0.48159 (7)0.0289 (3)
C280.14132 (15)0.85432 (11)0.54677 (7)0.0275 (3)
C290.06147 (16)0.82926 (12)0.61151 (7)0.0289 (3)
H290.03640.76110.61960.035*
C300.01899 (16)0.90582 (12)0.66422 (8)0.0296 (3)
C310.05450 (17)1.00664 (12)0.65041 (8)0.0325 (3)
H310.02401.05840.68660.039*
C320.13222 (17)1.03442 (12)0.58634 (8)0.0333 (3)
H320.15441.10350.57750.040*
C330.17505 (16)0.95539 (11)0.53641 (7)0.0287 (3)
C340.27741 (16)0.86767 (12)0.43847 (7)0.0296 (3)
C350.06404 (16)0.88143 (12)0.73604 (8)0.0315 (3)
H350.08850.94900.76390.038*
C360.0381 (2)0.78558 (16)0.77551 (8)0.0457 (4)
H36A0.13430.80310.77980.055*
H36B0.06790.71770.74840.055*
C370.0454 (2)0.76366 (17)0.84885 (9)0.0518 (4)
H37A0.02160.69800.87150.062*
H37B0.06390.82820.87790.062*
C380.1988 (3)0.74368 (17)0.84541 (10)0.0560 (5)
H38A0.17930.67370.82170.067*
H38B0.25350.73560.89360.067*
C390.3007 (2)0.83800 (17)0.80619 (9)0.0476 (4)
H39A0.33100.90610.83320.057*
H39B0.39660.81990.80200.057*
C400.21765 (18)0.85977 (15)0.73291 (8)0.0398 (4)
H40A0.19810.79480.70410.048*
H40B0.28530.92480.71000.048*
C410.37181 (16)0.85823 (12)0.36844 (7)0.0304 (3)
C420.50058 (17)0.89865 (13)0.35564 (8)0.0350 (3)
H420.52510.93260.39200.042*
C430.59281 (19)0.88949 (13)0.29019 (9)0.0408 (4)
H430.68080.91660.28120.049*
C440.5541 (2)0.84021 (13)0.23855 (8)0.0414 (4)
C450.4275 (2)0.80065 (14)0.24890 (8)0.0418 (4)
H450.40340.76760.21200.050*
C460.33557 (18)0.81000 (13)0.31451 (8)0.0368 (3)
H460.24720.78330.32270.044*
C470.25088 (16)0.58364 (11)0.52907 (7)0.0289 (3)
C480.16850 (18)0.50752 (13)0.54914 (8)0.0374 (3)
H480.08330.50990.52680.045*
C490.2099 (2)0.42799 (15)0.60171 (9)0.0446 (4)
H490.15290.37600.61560.054*
C500.3341 (2)0.42435 (13)0.63383 (9)0.0411 (4)
H500.36290.36980.66990.049*
C510.41641 (18)0.50015 (13)0.61351 (8)0.0379 (3)
H510.50170.49740.63600.046*
C520.37666 (17)0.58023 (12)0.56091 (8)0.0341 (3)
H520.43430.63180.54690.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02799 (17)0.02660 (17)0.02791 (17)0.00381 (13)0.00096 (13)0.00506 (13)
F10.0534 (6)0.0455 (5)0.0388 (5)0.0197 (4)0.0164 (4)0.0151 (4)
O10.0299 (5)0.0274 (5)0.0303 (5)0.0052 (4)0.0018 (4)0.0032 (4)
O20.0408 (6)0.0461 (6)0.0321 (6)0.0108 (5)0.0057 (5)0.0099 (5)
C10.0247 (6)0.0263 (6)0.0279 (7)0.0058 (5)0.0032 (5)0.0034 (5)
C20.0239 (6)0.0252 (6)0.0313 (7)0.0060 (5)0.0039 (5)0.0054 (5)
C30.0253 (7)0.0272 (6)0.0305 (7)0.0054 (5)0.0030 (5)0.0040 (5)
C40.0268 (7)0.0273 (7)0.0337 (7)0.0069 (5)0.0061 (6)0.0044 (6)
C50.0281 (7)0.0265 (7)0.0415 (8)0.0026 (5)0.0016 (6)0.0063 (6)
C60.0283 (7)0.0298 (7)0.0379 (8)0.0050 (6)0.0038 (6)0.0070 (6)
C70.0280 (7)0.0276 (7)0.0305 (7)0.0092 (5)0.0013 (6)0.0041 (5)
C80.0256 (6)0.0275 (6)0.0300 (7)0.0078 (5)0.0023 (5)0.0057 (5)
C90.0277 (7)0.0257 (6)0.0342 (7)0.0013 (5)0.0052 (6)0.0027 (6)
C100.0769 (13)0.0317 (8)0.0348 (9)0.0002 (8)0.0135 (8)0.0024 (7)
C110.0766 (14)0.0425 (10)0.0307 (8)0.0114 (9)0.0045 (9)0.0003 (7)
C120.0541 (12)0.0775 (15)0.0591 (13)0.0066 (11)0.0084 (10)0.0296 (11)
C130.0655 (13)0.0606 (12)0.0668 (13)0.0370 (10)0.0172 (11)0.0214 (10)
C140.0540 (10)0.0463 (9)0.0511 (10)0.0245 (8)0.0179 (8)0.0088 (8)
C150.0307 (7)0.0294 (7)0.0271 (7)0.0121 (5)0.0047 (6)0.0021 (5)
C160.0290 (7)0.0339 (7)0.0310 (7)0.0107 (6)0.0031 (6)0.0004 (6)
C170.0317 (7)0.0342 (7)0.0366 (8)0.0101 (6)0.0097 (6)0.0008 (6)
C180.0420 (8)0.0339 (7)0.0308 (7)0.0180 (6)0.0135 (6)0.0049 (6)
C190.0412 (8)0.0439 (8)0.0290 (7)0.0176 (7)0.0008 (6)0.0008 (6)
C200.0330 (8)0.0356 (8)0.0326 (8)0.0082 (6)0.0002 (6)0.0029 (6)
C210.0252 (7)0.0286 (7)0.0314 (7)0.0030 (5)0.0011 (6)0.0032 (6)
C220.0381 (8)0.0441 (9)0.0333 (8)0.0102 (7)0.0009 (6)0.0006 (7)
C230.0537 (11)0.0563 (11)0.0508 (11)0.0228 (9)0.0069 (9)0.0048 (9)
C240.0481 (10)0.0618 (12)0.0690 (13)0.0306 (9)0.0061 (9)0.0120 (10)
C250.0454 (10)0.0648 (12)0.0546 (11)0.0243 (9)0.0049 (8)0.0156 (9)
C260.0376 (8)0.0459 (9)0.0339 (8)0.0125 (7)0.0034 (7)0.0053 (7)
S20.03003 (18)0.03542 (19)0.02744 (17)0.01091 (14)0.00264 (14)0.00723 (14)
F20.0748 (8)0.0594 (7)0.0381 (5)0.0195 (6)0.0184 (5)0.0014 (5)
O30.0320 (5)0.0322 (5)0.0297 (5)0.0106 (4)0.0051 (4)0.0005 (4)
O40.0364 (6)0.0465 (6)0.0418 (6)0.0160 (5)0.0130 (5)0.0062 (5)
C270.0259 (7)0.0339 (7)0.0276 (7)0.0093 (6)0.0040 (5)0.0036 (6)
C280.0242 (6)0.0297 (7)0.0295 (7)0.0066 (5)0.0072 (5)0.0039 (5)
C290.0264 (7)0.0296 (7)0.0314 (7)0.0092 (5)0.0031 (6)0.0040 (6)
C300.0243 (6)0.0328 (7)0.0313 (7)0.0067 (5)0.0039 (5)0.0052 (6)
C310.0308 (7)0.0305 (7)0.0352 (8)0.0059 (6)0.0046 (6)0.0080 (6)
C320.0339 (7)0.0269 (7)0.0397 (8)0.0091 (6)0.0071 (6)0.0022 (6)
C330.0252 (6)0.0315 (7)0.0290 (7)0.0075 (5)0.0060 (5)0.0018 (5)
C340.0255 (7)0.0342 (7)0.0302 (7)0.0080 (6)0.0086 (6)0.0018 (6)
C350.0310 (7)0.0343 (7)0.0297 (7)0.0102 (6)0.0006 (6)0.0088 (6)
C360.0388 (9)0.0591 (11)0.0320 (8)0.0042 (8)0.0046 (7)0.0016 (7)
C370.0555 (11)0.0612 (11)0.0321 (8)0.0095 (9)0.0051 (8)0.0021 (8)
C380.0765 (14)0.0604 (11)0.0371 (9)0.0361 (10)0.0025 (9)0.0002 (8)
C390.0418 (9)0.0705 (12)0.0381 (9)0.0308 (9)0.0032 (7)0.0094 (8)
C400.0342 (8)0.0537 (10)0.0348 (8)0.0185 (7)0.0033 (6)0.0026 (7)
C410.0284 (7)0.0340 (7)0.0276 (7)0.0080 (6)0.0053 (6)0.0028 (6)
C420.0327 (7)0.0376 (8)0.0346 (8)0.0109 (6)0.0047 (6)0.0002 (6)
C430.0368 (8)0.0404 (8)0.0431 (9)0.0142 (7)0.0018 (7)0.0031 (7)
C440.0475 (9)0.0381 (8)0.0294 (8)0.0076 (7)0.0057 (7)0.0041 (6)
C450.0527 (10)0.0447 (9)0.0278 (7)0.0130 (7)0.0085 (7)0.0002 (7)
C460.0376 (8)0.0451 (9)0.0299 (7)0.0146 (7)0.0088 (6)0.0026 (6)
C470.0267 (7)0.0310 (7)0.0288 (7)0.0080 (5)0.0006 (5)0.0089 (6)
C480.0342 (8)0.0464 (9)0.0379 (8)0.0196 (7)0.0065 (6)0.0050 (7)
C490.0510 (10)0.0462 (9)0.0440 (9)0.0268 (8)0.0065 (8)0.0017 (7)
C500.0508 (10)0.0372 (8)0.0349 (8)0.0111 (7)0.0083 (7)0.0026 (7)
C510.0363 (8)0.0395 (8)0.0395 (8)0.0074 (6)0.0125 (7)0.0091 (7)
C520.0319 (7)0.0346 (7)0.0398 (8)0.0134 (6)0.0057 (6)0.0087 (6)
Geometric parameters (Å, º) top
S1—O21.4832 (11)S2—O41.4955 (11)
S1—C11.7681 (13)S2—C271.7589 (14)
S1—C211.8020 (15)S2—C471.7948 (15)
F1—C181.3541 (16)F2—C441.3546 (18)
O1—C71.3778 (17)O3—C341.3687 (17)
O1—C81.3821 (16)O3—C331.3801 (17)
C1—C81.3649 (19)C27—C341.363 (2)
C1—C21.4457 (18)C27—C281.4504 (19)
C2—C71.3917 (19)C28—C331.3931 (19)
C2—C31.394 (2)C28—C291.3959 (19)
C3—C41.3948 (19)C29—C301.3960 (19)
C3—H30.9500C29—H290.9500
C4—C51.409 (2)C30—C311.401 (2)
C4—C91.510 (2)C30—C351.515 (2)
C5—C61.384 (2)C31—C321.388 (2)
C5—H50.9500C31—H310.9500
C6—C71.380 (2)C32—C331.378 (2)
C6—H60.9500C32—H320.9500
C8—C151.4602 (19)C34—C411.467 (2)
C9—C101.518 (2)C35—C401.524 (2)
C9—C141.526 (2)C35—C361.527 (2)
C9—H91.0000C35—H351.0000
C10—C111.524 (2)C36—C371.532 (2)
C10—H10A0.9900C36—H36A0.9900
C10—H10B0.9900C36—H36B0.9900
C11—C121.515 (3)C37—C381.515 (3)
C11—H11A0.9900C37—H37A0.9900
C11—H11B0.9900C37—H37B0.9900
C12—C131.512 (3)C38—C391.512 (3)
C12—H12A0.9900C38—H38A0.9900
C12—H12B0.9900C38—H38B0.9900
C13—C141.527 (2)C39—C401.530 (2)
C13—H13A0.9900C39—H39A0.9900
C13—H13B0.9900C39—H39B0.9900
C14—H14A0.9900C40—H40A0.9900
C14—H14B0.9900C40—H40B0.9900
C15—C201.398 (2)C41—C461.393 (2)
C15—C161.398 (2)C41—C421.396 (2)
C16—C171.385 (2)C42—C431.386 (2)
C16—H160.9500C42—H420.9500
C17—C181.377 (2)C43—C441.376 (2)
C17—H170.9500C43—H430.9500
C18—C191.375 (2)C44—C451.372 (2)
C19—C201.384 (2)C45—C461.388 (2)
C19—H190.9500C45—H450.9500
C20—H200.9500C46—H460.9500
C21—C221.379 (2)C47—C481.383 (2)
C21—C261.387 (2)C47—C521.389 (2)
C22—C231.395 (3)C48—C491.383 (2)
C22—H220.9500C48—H480.9500
C23—C241.378 (3)C49—C501.378 (2)
C23—H230.9500C49—H490.9500
C24—C251.381 (3)C50—C511.380 (2)
C24—H240.9500C50—H500.9500
C25—C261.381 (2)C51—C521.385 (2)
C25—H250.9500C51—H510.9500
C26—H260.9500C52—H520.9500
O2—S1—C1106.57 (6)O4—S2—C27108.81 (6)
O2—S1—C21107.16 (7)O4—S2—C47106.56 (6)
C1—S1—C2197.93 (6)C27—S2—C47100.12 (6)
C7—O1—C8106.71 (10)C34—O3—C33106.37 (11)
C8—C1—C2107.55 (12)C34—C27—C28106.99 (12)
C8—C1—S1128.04 (11)C34—C27—S2121.59 (11)
C2—C1—S1123.92 (10)C28—C27—S2131.29 (11)
C7—C2—C3119.91 (12)C33—C28—C29119.07 (13)
C7—C2—C1104.85 (12)C33—C28—C27104.63 (12)
C3—C2—C1135.24 (13)C29—C28—C27136.27 (13)
C2—C3—C4118.67 (13)C28—C29—C30119.00 (13)
C2—C3—H3120.7C28—C29—H29120.5
C4—C3—H3120.7C30—C29—H29120.5
C3—C4—C5119.18 (13)C29—C30—C31119.30 (13)
C3—C4—C9120.78 (13)C29—C30—C35121.13 (13)
C5—C4—C9119.98 (12)C31—C30—C35119.57 (12)
C6—C5—C4123.00 (13)C32—C31—C30123.01 (13)
C6—C5—H5118.5C32—C31—H31118.5
C4—C5—H5118.5C30—C31—H31118.5
C7—C6—C5116.03 (13)C33—C32—C31115.71 (13)
C7—C6—H6122.0C33—C32—H32122.1
C5—C6—H6122.0C31—C32—H32122.1
O1—C7—C6126.08 (13)C32—C33—O3125.28 (13)
O1—C7—C2110.72 (11)C32—C33—C28123.87 (13)
C6—C7—C2123.19 (13)O3—C33—C28110.84 (12)
C1—C8—O1110.16 (12)C27—C34—O3111.17 (12)
C1—C8—C15135.74 (13)C27—C34—C41134.11 (13)
O1—C8—C15114.09 (12)O3—C34—C41114.62 (12)
C4—C9—C10113.60 (12)C30—C35—C40112.57 (12)
C4—C9—C14110.00 (12)C30—C35—C36112.15 (12)
C10—C9—C14111.43 (14)C40—C35—C36110.28 (13)
C4—C9—H9107.2C30—C35—H35107.2
C10—C9—H9107.2C40—C35—H35107.2
C14—C9—H9107.2C36—C35—H35107.2
C9—C10—C11111.83 (14)C35—C36—C37111.74 (14)
C9—C10—H10A109.3C35—C36—H36A109.3
C11—C10—H10A109.3C37—C36—H36A109.3
C9—C10—H10B109.3C35—C36—H36B109.3
C11—C10—H10B109.3C37—C36—H36B109.3
H10A—C10—H10B107.9H36A—C36—H36B107.9
C12—C11—C10111.41 (17)C38—C37—C36111.32 (15)
C12—C11—H11A109.3C38—C37—H37A109.4
C10—C11—H11A109.3C36—C37—H37A109.4
C12—C11—H11B109.3C38—C37—H37B109.4
C10—C11—H11B109.3C36—C37—H37B109.4
H11A—C11—H11B108.0H37A—C37—H37B108.0
C13—C12—C11111.13 (16)C39—C38—C37111.42 (15)
C13—C12—H12A109.4C39—C38—H38A109.3
C11—C12—H12A109.4C37—C38—H38A109.3
C13—C12—H12B109.4C39—C38—H38B109.3
C11—C12—H12B109.4C37—C38—H38B109.3
H12A—C12—H12B108.0H38A—C38—H38B108.0
C12—C13—C14110.90 (17)C38—C39—C40111.69 (15)
C12—C13—H13A109.5C38—C39—H39A109.3
C14—C13—H13A109.5C40—C39—H39A109.3
C12—C13—H13B109.5C38—C39—H39B109.3
C14—C13—H13B109.5C40—C39—H39B109.3
H13A—C13—H13B108.0H39A—C39—H39B107.9
C9—C14—C13111.28 (14)C35—C40—C39111.48 (13)
C9—C14—H14A109.4C35—C40—H40A109.3
C13—C14—H14A109.4C39—C40—H40A109.3
C9—C14—H14B109.4C35—C40—H40B109.3
C13—C14—H14B109.4C39—C40—H40B109.3
H14A—C14—H14B108.0H40A—C40—H40B108.0
C20—C15—C16118.54 (13)C46—C41—C42119.38 (14)
C20—C15—C8119.35 (13)C46—C41—C34121.44 (13)
C16—C15—C8122.09 (13)C42—C41—C34119.18 (13)
C17—C16—C15120.69 (14)C43—C42—C41120.32 (15)
C17—C16—H16119.7C43—C42—H42119.8
C15—C16—H16119.7C41—C42—H42119.8
C18—C17—C16118.55 (14)C44—C43—C42118.51 (15)
C18—C17—H17120.7C44—C43—H43120.7
C16—C17—H17120.7C42—C43—H43120.7
F1—C18—C19118.68 (14)F2—C44—C45118.84 (16)
F1—C18—C17118.49 (14)F2—C44—C43118.30 (15)
C19—C18—C17122.83 (14)C45—C44—C43122.86 (15)
C18—C19—C20118.03 (14)C44—C45—C46118.41 (15)
C18—C19—H19121.0C44—C45—H45120.8
C20—C19—H19121.0C46—C45—H45120.8
C19—C20—C15121.35 (14)C45—C46—C41120.52 (15)
C19—C20—H20119.3C45—C46—H46119.7
C15—C20—H20119.3C41—C46—H46119.7
C22—C21—C26121.79 (14)C48—C47—C52120.39 (14)
C22—C21—S1118.64 (12)C48—C47—S2116.89 (11)
C26—C21—S1119.36 (11)C52—C47—S2122.14 (11)
C21—C22—C23118.21 (16)C47—C48—C49120.16 (14)
C21—C22—H22120.9C47—C48—H48119.9
C23—C22—H22120.9C49—C48—H48119.9
C24—C23—C22120.53 (17)C50—C49—C48119.84 (15)
C24—C23—H23119.7C50—C49—H49120.1
C22—C23—H23119.7C48—C49—H49120.1
C23—C24—C25120.37 (17)C49—C50—C51119.87 (15)
C23—C24—H24119.8C49—C50—H50120.1
C25—C24—H24119.8C51—C50—H50120.1
C24—C25—C26120.06 (17)C50—C51—C52121.04 (14)
C24—C25—H25120.0C50—C51—H51119.5
C26—C25—H25120.0C52—C51—H51119.5
C25—C26—C21119.04 (16)C51—C52—C47118.70 (14)
C25—C26—H26120.5C51—C52—H52120.6
C21—C26—H26120.5C47—C52—H52120.6
O2—S1—C1—C8129.92 (13)O4—S2—C27—C34110.88 (12)
C21—S1—C1—C8119.46 (13)C47—S2—C27—C34137.62 (12)
O2—S1—C1—C241.04 (13)O4—S2—C27—C2864.38 (15)
C21—S1—C1—C269.59 (12)C47—S2—C27—C2847.12 (14)
C8—C1—C2—C70.03 (15)C34—C27—C28—C330.14 (15)
S1—C1—C2—C7172.51 (10)S2—C27—C28—C33175.64 (11)
C8—C1—C2—C3179.17 (15)C34—C27—C28—C29177.66 (15)
S1—C1—C2—C38.3 (2)S2—C27—C28—C296.6 (3)
C7—C2—C3—C40.5 (2)C33—C28—C29—C300.6 (2)
C1—C2—C3—C4178.65 (14)C27—C28—C29—C30176.98 (15)
C2—C3—C4—C51.3 (2)C28—C29—C30—C311.4 (2)
C2—C3—C4—C9175.88 (12)C28—C29—C30—C35178.37 (12)
C3—C4—C5—C60.9 (2)C29—C30—C31—C320.7 (2)
C9—C4—C5—C6176.23 (14)C35—C30—C31—C32179.06 (13)
C4—C5—C6—C70.2 (2)C30—C31—C32—C330.8 (2)
C8—O1—C7—C6179.79 (14)C31—C32—C33—O3177.75 (13)
C8—O1—C7—C20.35 (15)C31—C32—C33—C281.6 (2)
C5—C6—C7—O1178.77 (13)C34—O3—C33—C32178.94 (13)
C5—C6—C7—C21.1 (2)C34—O3—C33—C280.50 (15)
C3—C2—C7—O1179.12 (12)C29—C28—C33—C321.0 (2)
C1—C2—C7—O10.24 (15)C27—C28—C33—C32179.23 (13)
C3—C2—C7—C60.7 (2)C29—C28—C33—O3178.49 (11)
C1—C2—C7—C6179.89 (13)C27—C28—C33—O30.22 (15)
C2—C1—C8—O10.18 (15)C28—C27—C34—O30.47 (16)
S1—C1—C8—O1172.32 (10)S2—C27—C34—O3175.81 (9)
C2—C1—C8—C15178.81 (15)C28—C27—C34—C41175.71 (14)
S1—C1—C8—C159.0 (2)S2—C27—C34—C418.0 (2)
C7—O1—C8—C10.33 (15)C33—O3—C34—C270.60 (15)
C7—O1—C8—C15179.28 (11)C33—O3—C34—C41176.38 (11)
C3—C4—C9—C1040.31 (19)C29—C30—C35—C4058.93 (18)
C5—C4—C9—C10142.58 (15)C31—C30—C35—C40121.35 (15)
C3—C4—C9—C1485.36 (17)C29—C30—C35—C3666.13 (18)
C5—C4—C9—C1491.75 (16)C31—C30—C35—C36113.59 (16)
C4—C9—C10—C11178.30 (15)C30—C35—C36—C37178.43 (14)
C14—C9—C10—C1153.4 (2)C40—C35—C36—C3755.25 (19)
C9—C10—C11—C1254.3 (2)C35—C36—C37—C3855.3 (2)
C10—C11—C12—C1356.0 (2)C36—C37—C38—C3954.7 (2)
C11—C12—C13—C1456.8 (2)C37—C38—C39—C4055.0 (2)
C4—C9—C14—C13178.92 (15)C30—C35—C40—C39178.71 (14)
C10—C9—C14—C1354.2 (2)C36—C35—C40—C3955.21 (18)
C12—C13—C14—C955.9 (2)C38—C39—C40—C3555.58 (19)
C1—C8—C15—C20169.42 (16)C27—C34—C41—C4642.2 (2)
O1—C8—C15—C2011.98 (18)O3—C34—C41—C46141.70 (14)
C1—C8—C15—C1612.2 (2)C27—C34—C41—C42137.88 (17)
O1—C8—C15—C16166.43 (12)O3—C34—C41—C4238.20 (18)
C20—C15—C16—C170.4 (2)C46—C41—C42—C430.9 (2)
C8—C15—C16—C17178.83 (13)C34—C41—C42—C43179.18 (14)
C15—C16—C17—C180.4 (2)C41—C42—C43—C440.2 (2)
C16—C17—C18—F1178.38 (12)C42—C43—C44—F2179.64 (14)
C16—C17—C18—C190.6 (2)C42—C43—C44—C450.6 (3)
F1—C18—C19—C20178.28 (13)F2—C44—C45—C46179.63 (14)
C17—C18—C19—C200.7 (2)C43—C44—C45—C460.6 (3)
C18—C19—C20—C150.7 (2)C44—C45—C46—C410.2 (2)
C16—C15—C20—C190.5 (2)C42—C41—C46—C450.9 (2)
C8—C15—C20—C19178.99 (14)C34—C41—C46—C45179.20 (14)
O2—S1—C21—C2210.24 (14)O4—S2—C47—C4825.64 (13)
C1—S1—C21—C22120.38 (12)C27—S2—C47—C48138.89 (12)
O2—S1—C21—C26174.99 (11)O4—S2—C47—C52163.09 (12)
C1—S1—C21—C2664.85 (13)C27—S2—C47—C5249.83 (13)
C26—C21—C22—C230.6 (2)C52—C47—C48—C490.7 (2)
S1—C21—C22—C23175.20 (13)S2—C47—C48—C49172.11 (13)
C21—C22—C23—C240.9 (3)C47—C48—C49—C500.4 (3)
C22—C23—C24—C250.9 (3)C48—C49—C50—C510.1 (3)
C23—C24—C25—C260.6 (3)C49—C50—C51—C520.2 (2)
C24—C25—C26—C210.2 (3)C50—C51—C52—C470.5 (2)
C22—C21—C26—C250.2 (2)C48—C47—C52—C510.7 (2)
S1—C21—C26—C25174.83 (13)S2—C47—C52—C51171.72 (11)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C41–C46 4-fluorophenyl ring and the C2–C7 benzene ring, respectively.
D—H···AD—HH···AD···AD—H···A
C10—H10B···O2i0.992.473.384 (2)153
C22—H22···O2i0.952.423.2365 (19)144
C19—H19···O4ii0.952.443.3442 (19)159
C40—H40B···Cg1iii0.992.843.763 (2)155
C45—H45···Cg20.952.823.602 (2)140
C50—H50···Cg1iv0.952.803.619 (2)144
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1; (iii) x, y+2, z+1; (iv) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C41–C46 4-fluorophenyl ring and the C2–C7 benzene ring, respectively.
D—H···AD—HH···AD···AD—H···A
C10—H10B···O2i0.992.473.384 (2)152.9
C22—H22···O2i0.952.423.2365 (19)144.0
C19—H19···O4ii0.952.443.3442 (19)159.4
C40—H40B···Cg1iii0.992.843.763 (2)155.0
C45—H45···Cg20.952.823.602 (2)140.3
C50—H50···Cg1iv0.952.803.619 (2)144.3
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z+1; (iii) x, y+2, z+1; (iv) x+1, y+1, z+1.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
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