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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-(4-Fluoro­phen­yl)-2-(4-methyl­phen­yl)-3-methyl­sulfanyl-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 27 January 2014; accepted 3 February 2014; online 8 February 2014)

The asymmetric unit of the title compound, C22H17FOS, contains two independent mol­ecules (A and B). The dihedral angles between the benzo­furan ring systems [r.m.s. deviations of 0.026 (1), 0.004 (1) and 0.003 (1) Å, respectively, for mol­ecule A, and 0.002 (1), 0.004 (1) and 0.005 (1) Å for B] and the pendant 4-fluoro­phenyl and 4-methyl­phenyl rings are 39.48 (4) and 30.86 (5)°, respectively, for mol­ecule A, and 33.34 (6) and 20.99 (8)° for B. In the crystal, mol­ecules are linked by weak C—H⋯F 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. (2011a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o782.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o2742.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17FOS

  • Mr = 348.42

  • Monoclinic, P 21 /c

  • a = 17.897 (6) Å

  • b = 10.753 (3) Å

  • c = 17.775 (5) Å

  • β = 98.541 (18)°

  • V = 3382.8 (18) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 173 K

  • 0.43 × 0.36 × 0.12 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 = 0.681, Tmax = 0.746

  • 55108 measured reflections

  • 7388 independent reflections

  • 5723 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.114

  • S = 1.03

  • 7388 reflections

  • 454 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 4-methyl­phenyl ring

D—H⋯A D—H H⋯A DA D—H⋯A
C28—H28⋯F2i 0.95 2.43 3.267 (2) 147
C44—H44C⋯F1ii 0.98 2.52 3.359 (2) 143
C32—H32⋯Cg1iii 0.95 2.69 3.465 (2) 139
C36—H36⋯Cg1iv 0.95 2.67 3.468 (2) 143
Symmetry codes: (i) x, y-1, z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y+1, z; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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 5-(4-fluorophenyl)-3-methylsulfanyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2011a), phenyl (Choi et al., 2011b) substituents in 2-position, we report here the crystal structure of the title compound which crystallizes with two symmetrically independent molecules, A & B, in the asymmetric unit.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.026 (1) and 0.002 (1) Å, for A and B, respectively, from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl and 4-methylphenyl rings are essentially planar, with mean deviations of 0.004 (1) and 0.003 (1) for molecule A, and 0.004 (1) and 0.005 (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 4-methylphenyl rings are 39.48 (4) and 30.86 (5)° in molecule A, and 33.34 (6) and 20.99 (8)° in molecule B, respectively. In the crystal structure (Fig. 2 & 3), molecules are connected by weak C—H···F and C—H···π interactions (Table 2, Cg1 is the centroid of the C15–C20 4-methylphenyl ring), resulting in a three-dimensional network.

Related literature top

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

Experimental top

Zinc chloride (286 mg, 2.1 mmol) was added to a stirred solution of 4-fluoro-4'-hydroxybiphenyl (376 mg, 2.0 mmol) and 2-chloro-4'-methyl-2-methylsulfanylacetophenone (429 mg, 2.0 mmol) in dichloromethane (40 mL) at room temperature, and stirring was continued at the same temperature for 1h. The reaction was quenched by the addition of water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-benzene, 5:2 v/v) to afford the title compound as a colorless solid [yield 56%, m.p. 425–426 K; Rf = 0.56 (hexane–benzene, 5:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in carbon tetrachloride 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 and 0.98 Å for methyl H atoms, respectively. Uiso (H) = 1.2Ueq (C) for aryl 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···F 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, y - 1, z (ii) - x, y - 1/2, - z + 1/2 (iii) x, y + 1, z; (v) - x, y + 1/2, - z + 1/2.]
[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, y + 1, z; (iv) x, - y + 1/2, z - 1/2; (vi) x, y - 1, z; (vii) x, - y + 1/2, z + 1/2.]
5-(4-Fluorophenyl)-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran top
Crystal data top
C22H17FOSF(000) = 1456
Mr = 348.42Dx = 1.368 Mg m3
Monoclinic, P21/cMelting point = 425–426 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 17.897 (6) ÅCell parameters from 9590 reflections
b = 10.753 (3) Åθ = 2.2–26.3°
c = 17.775 (5) ŵ = 0.21 mm1
β = 98.541 (18)°T = 173 K
V = 3382.8 (18) Å3Block, colourless
Z = 80.43 × 0.36 × 0.12 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
7388 independent reflections
Radiation source: rotating anode5723 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.051
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.2°
φ and ω scansh = 2222
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1313
Tmin = 0.681, Tmax = 0.746l = 2222
55108 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)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.114H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0548P)2 + 1.2362P]
where P = (Fo2 + 2Fc2)/3
7388 reflections(Δ/σ)max = 0.001
454 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C22H17FOSV = 3382.8 (18) Å3
Mr = 348.42Z = 8
Monoclinic, P21/cMo Kα radiation
a = 17.897 (6) ŵ = 0.21 mm1
b = 10.753 (3) ÅT = 173 K
c = 17.775 (5) Å0.43 × 0.36 × 0.12 mm
β = 98.541 (18)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
7388 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5723 reflections with I > 2σ(I)
Tmin = 0.681, Tmax = 0.746Rint = 0.051
55108 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.03Δρmax = 0.33 e Å3
7388 reflectionsΔρmin = 0.37 e Å3
454 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
S10.37299 (2)0.21067 (4)0.29473 (2)0.02650 (11)
F10.06413 (7)0.84290 (10)0.44228 (7)0.0486 (3)
O10.23646 (6)0.00311 (10)0.39568 (7)0.0263 (3)
C10.30874 (9)0.14077 (15)0.34763 (9)0.0237 (3)
C20.25213 (9)0.20428 (15)0.38362 (9)0.0241 (3)
C30.23108 (9)0.32782 (15)0.39093 (9)0.0252 (4)
H30.25940.39310.37280.030*
C40.16752 (9)0.35447 (15)0.42539 (9)0.0262 (4)
C50.12703 (10)0.25676 (16)0.45380 (10)0.0290 (4)
H50.08470.27630.47810.035*
C60.14701 (10)0.13436 (16)0.44740 (10)0.0288 (4)
H60.11960.06880.46640.035*
C70.20949 (9)0.11165 (15)0.41162 (9)0.0253 (4)
C80.29684 (9)0.01726 (15)0.35648 (9)0.0241 (3)
C90.14098 (9)0.48411 (15)0.43128 (9)0.0261 (4)
C100.06343 (10)0.51114 (17)0.42028 (10)0.0316 (4)
H100.02810.44510.41010.038*
C110.03721 (10)0.63092 (18)0.42381 (10)0.0352 (4)
H110.01540.64850.41580.042*
C120.08954 (11)0.72404 (16)0.43927 (10)0.0336 (4)
C130.16654 (11)0.70297 (17)0.45160 (10)0.0327 (4)
H130.20120.76970.46290.039*
C140.19175 (10)0.58206 (16)0.44707 (10)0.0293 (4)
H140.24450.56560.45480.035*
C150.33306 (9)0.09598 (15)0.33398 (9)0.0246 (3)
C160.41086 (9)0.10156 (16)0.32995 (9)0.0274 (4)
H160.44120.02930.34050.033*
C170.44362 (10)0.21136 (16)0.31081 (9)0.0286 (4)
H170.49630.21350.30840.034*
C180.40082 (10)0.31842 (15)0.29508 (9)0.0277 (4)
C190.32341 (10)0.31272 (15)0.30001 (9)0.0277 (4)
H190.29340.38540.29010.033*
C200.28997 (10)0.20375 (15)0.31890 (9)0.0265 (4)
H200.23740.20210.32170.032*
C210.43623 (11)0.43679 (17)0.27212 (11)0.0371 (4)
H21A0.47640.46280.31270.045*
H21B0.45770.42260.22520.045*
H21C0.39770.50200.26350.045*
C220.45009 (10)0.24833 (18)0.36934 (11)0.0375 (4)
H22A0.43140.30140.40730.056*
H22B0.48960.29250.34740.056*
H22C0.47100.17150.39360.056*
S20.12675 (3)0.49163 (4)0.20081 (3)0.03560 (13)
F20.41994 (6)1.12966 (9)0.04363 (7)0.0422 (3)
O20.27237 (6)0.27471 (10)0.11261 (6)0.0262 (3)
C230.19837 (9)0.41799 (16)0.15898 (9)0.0270 (4)
C240.25573 (9)0.48150 (15)0.12453 (9)0.0256 (4)
C250.27344 (9)0.60571 (15)0.11360 (9)0.0253 (3)
H250.24420.67010.13150.030*
C260.33444 (9)0.63484 (15)0.07614 (9)0.0239 (3)
C270.37678 (9)0.53799 (16)0.04921 (10)0.0267 (4)
H270.41800.55870.02350.032*
C280.36017 (9)0.41427 (15)0.05910 (10)0.0274 (4)
H280.38890.34950.04100.033*
C290.29921 (9)0.38949 (15)0.09688 (9)0.0249 (4)
C300.21047 (9)0.29419 (15)0.15035 (9)0.0252 (3)
C310.35593 (9)0.76637 (15)0.06618 (9)0.0232 (3)
C320.34603 (9)0.85462 (15)0.12153 (9)0.0259 (4)
H320.32430.83000.16490.031*
C330.36720 (9)0.97693 (15)0.11432 (10)0.0277 (4)
H330.36071.03660.15220.033*
C340.39803 (10)1.01017 (15)0.05080 (10)0.0291 (4)
C350.40837 (9)0.92699 (16)0.00564 (10)0.0282 (4)
H350.42940.95290.04910.034*
C360.38730 (9)0.80506 (15)0.00268 (9)0.0254 (3)
H360.39420.74620.03550.030*
C370.17303 (9)0.18137 (15)0.17111 (9)0.0251 (4)
C380.12785 (10)0.17959 (17)0.22887 (10)0.0312 (4)
H380.12010.25420.25530.037*
C390.09441 (10)0.07072 (17)0.24784 (10)0.0335 (4)
H390.06350.07180.28690.040*
C400.10489 (10)0.04023 (17)0.21115 (10)0.0308 (4)
C410.14927 (10)0.03773 (17)0.15302 (11)0.0336 (4)
H410.15650.11240.12650.040*
C420.18297 (10)0.07025 (16)0.13297 (10)0.0291 (4)
H420.21300.06910.09320.035*
C430.06869 (12)0.15786 (18)0.23410 (12)0.0441 (5)
H43A0.05260.14610.28400.066*
H43B0.10520.22620.23700.066*
H43C0.02470.17790.19630.066*
C440.07083 (11)0.5533 (2)0.11587 (12)0.0441 (5)
H44A0.10300.60400.08790.066*
H44B0.03000.60480.13010.066*
H44C0.04920.48450.08360.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0272 (2)0.0265 (2)0.0265 (2)0.00032 (16)0.00621 (17)0.00148 (16)
F10.0554 (7)0.0297 (6)0.0587 (7)0.0154 (5)0.0019 (6)0.0058 (5)
O10.0268 (6)0.0222 (6)0.0312 (6)0.0011 (5)0.0085 (5)0.0004 (5)
C10.0223 (8)0.0247 (8)0.0241 (8)0.0011 (6)0.0030 (7)0.0004 (6)
C20.0218 (8)0.0268 (8)0.0231 (8)0.0006 (6)0.0015 (7)0.0004 (6)
C30.0233 (8)0.0236 (8)0.0284 (8)0.0006 (6)0.0030 (7)0.0016 (7)
C40.0235 (8)0.0273 (9)0.0270 (8)0.0012 (7)0.0007 (7)0.0032 (7)
C50.0250 (9)0.0325 (9)0.0304 (9)0.0001 (7)0.0072 (7)0.0045 (7)
C60.0288 (9)0.0295 (9)0.0294 (9)0.0024 (7)0.0083 (7)0.0007 (7)
C70.0260 (9)0.0239 (8)0.0255 (8)0.0020 (6)0.0024 (7)0.0014 (6)
C80.0223 (8)0.0262 (8)0.0237 (8)0.0010 (6)0.0031 (7)0.0008 (6)
C90.0259 (9)0.0284 (9)0.0241 (8)0.0029 (7)0.0039 (7)0.0034 (7)
C100.0257 (9)0.0336 (10)0.0347 (9)0.0004 (7)0.0012 (8)0.0065 (8)
C110.0263 (9)0.0403 (11)0.0377 (10)0.0094 (8)0.0010 (8)0.0056 (8)
C120.0430 (11)0.0281 (9)0.0290 (9)0.0099 (8)0.0032 (8)0.0026 (7)
C130.0367 (10)0.0283 (9)0.0332 (9)0.0023 (8)0.0051 (8)0.0024 (7)
C140.0259 (9)0.0297 (9)0.0322 (9)0.0016 (7)0.0044 (7)0.0006 (7)
C150.0276 (9)0.0237 (8)0.0226 (8)0.0024 (7)0.0038 (7)0.0025 (6)
C160.0284 (9)0.0252 (8)0.0288 (9)0.0007 (7)0.0045 (7)0.0014 (7)
C170.0271 (9)0.0305 (9)0.0286 (9)0.0037 (7)0.0056 (7)0.0025 (7)
C180.0352 (9)0.0248 (8)0.0233 (8)0.0058 (7)0.0050 (7)0.0031 (7)
C190.0350 (10)0.0237 (8)0.0240 (8)0.0019 (7)0.0027 (7)0.0010 (7)
C200.0256 (8)0.0274 (9)0.0263 (8)0.0003 (7)0.0033 (7)0.0011 (7)
C210.0443 (11)0.0298 (10)0.0382 (10)0.0089 (8)0.0093 (9)0.0009 (8)
C220.0319 (10)0.0365 (10)0.0427 (11)0.0060 (8)0.0009 (8)0.0003 (8)
S20.0374 (3)0.0324 (3)0.0401 (3)0.00336 (19)0.0163 (2)0.00116 (19)
F20.0504 (7)0.0216 (5)0.0580 (7)0.0052 (5)0.0193 (6)0.0003 (5)
O20.0250 (6)0.0221 (6)0.0318 (6)0.0013 (4)0.0056 (5)0.0007 (5)
C230.0267 (9)0.0274 (9)0.0271 (8)0.0001 (7)0.0048 (7)0.0018 (7)
C240.0245 (8)0.0268 (9)0.0251 (8)0.0006 (7)0.0023 (7)0.0012 (7)
C250.0252 (8)0.0237 (8)0.0269 (8)0.0012 (6)0.0036 (7)0.0022 (7)
C260.0240 (8)0.0233 (8)0.0230 (8)0.0007 (6)0.0007 (7)0.0014 (6)
C270.0239 (8)0.0271 (9)0.0295 (9)0.0015 (7)0.0050 (7)0.0019 (7)
C280.0257 (9)0.0247 (9)0.0321 (9)0.0026 (7)0.0054 (7)0.0035 (7)
C290.0250 (8)0.0218 (8)0.0270 (8)0.0013 (6)0.0010 (7)0.0010 (6)
C300.0215 (8)0.0294 (9)0.0243 (8)0.0003 (7)0.0019 (7)0.0022 (7)
C310.0191 (8)0.0232 (8)0.0259 (8)0.0007 (6)0.0010 (6)0.0001 (6)
C320.0257 (9)0.0262 (9)0.0259 (8)0.0012 (7)0.0040 (7)0.0002 (7)
C330.0282 (9)0.0243 (8)0.0303 (9)0.0019 (7)0.0038 (7)0.0054 (7)
C340.0269 (9)0.0213 (8)0.0387 (10)0.0021 (7)0.0033 (8)0.0021 (7)
C350.0261 (9)0.0307 (9)0.0283 (9)0.0012 (7)0.0059 (7)0.0024 (7)
C360.0240 (8)0.0269 (8)0.0250 (8)0.0012 (7)0.0026 (7)0.0027 (7)
C370.0226 (8)0.0267 (8)0.0248 (8)0.0005 (6)0.0005 (7)0.0014 (7)
C380.0336 (10)0.0313 (9)0.0282 (9)0.0034 (7)0.0028 (8)0.0047 (7)
C390.0337 (10)0.0392 (10)0.0286 (9)0.0036 (8)0.0075 (8)0.0011 (8)
C400.0300 (9)0.0298 (9)0.0316 (9)0.0020 (7)0.0005 (7)0.0068 (7)
C410.0346 (10)0.0250 (9)0.0413 (10)0.0013 (7)0.0063 (8)0.0005 (8)
C420.0282 (9)0.0280 (9)0.0320 (9)0.0012 (7)0.0076 (7)0.0010 (7)
C430.0476 (12)0.0358 (11)0.0505 (12)0.0039 (9)0.0120 (10)0.0113 (9)
C440.0317 (10)0.0470 (12)0.0538 (13)0.0058 (9)0.0065 (9)0.0034 (10)
Geometric parameters (Å, º) top
S1—C11.7586 (17)S2—C231.7623 (18)
S1—C221.8119 (19)S2—C441.809 (2)
F1—C121.360 (2)F2—C341.3550 (19)
O1—C71.3699 (19)O2—C291.3683 (19)
O1—C81.388 (2)O2—C301.393 (2)
C1—C81.358 (2)C23—C301.361 (2)
C1—C21.447 (2)C23—C241.443 (2)
C2—C71.391 (2)C24—C291.393 (2)
C2—C31.392 (2)C24—C251.393 (2)
C3—C41.399 (2)C25—C261.396 (2)
C3—H30.9500C25—H250.9500
C4—C51.412 (2)C26—C271.413 (2)
C4—C91.481 (2)C26—C311.483 (2)
C5—C61.373 (2)C27—C281.380 (2)
C5—H50.9500C27—H270.9500
C6—C71.388 (2)C28—C291.389 (2)
C6—H60.9500C28—H280.9500
C8—C151.463 (2)C30—C371.460 (2)
C9—C141.392 (2)C31—C361.397 (2)
C9—C101.403 (2)C31—C321.397 (2)
C10—C111.375 (3)C32—C331.380 (2)
C10—H100.9500C32—H320.9500
C11—C121.371 (3)C33—C341.375 (3)
C11—H110.9500C33—H330.9500
C12—C131.382 (3)C34—C351.377 (2)
C13—C141.382 (2)C35—C361.378 (2)
C13—H130.9500C35—H350.9500
C14—H140.9500C36—H360.9500
C15—C201.396 (2)C37—C421.398 (2)
C15—C161.406 (2)C37—C381.398 (2)
C16—C171.383 (2)C38—C391.379 (3)
C16—H160.9500C38—H380.9500
C17—C181.388 (2)C39—C401.386 (3)
C17—H170.9500C39—H390.9500
C18—C191.402 (3)C40—C411.394 (3)
C18—C211.505 (2)C40—C431.505 (3)
C19—C201.380 (2)C41—C421.379 (2)
C19—H190.9500C41—H410.9500
C20—H200.9500C42—H420.9500
C21—H21A0.9800C43—H43A0.9800
C21—H21B0.9800C43—H43B0.9800
C21—H21C0.9800C43—H43C0.9800
C22—H22A0.9800C44—H44A0.9800
C22—H22B0.9800C44—H44B0.9800
C22—H22C0.9800C44—H44C0.9800
C1—S1—C22101.05 (9)C23—S2—C4499.18 (9)
C7—O1—C8106.64 (12)C29—O2—C30106.93 (12)
C8—C1—C2106.15 (14)C30—C23—C24106.25 (15)
C8—C1—S1127.32 (13)C30—C23—S2128.68 (14)
C2—C1—S1126.22 (12)C24—C23—S2125.05 (13)
C7—C2—C3118.64 (15)C29—C24—C25118.77 (16)
C7—C2—C1106.11 (14)C29—C24—C23106.47 (15)
C3—C2—C1135.11 (16)C25—C24—C23134.74 (16)
C2—C3—C4119.02 (16)C24—C25—C26119.46 (15)
C2—C3—H3120.5C24—C25—H25120.3
C4—C3—H3120.5C26—C25—H25120.3
C3—C4—C5119.87 (15)C25—C26—C27119.54 (15)
C3—C4—C9120.91 (15)C25—C26—C31120.39 (15)
C5—C4—C9119.21 (15)C27—C26—C31120.05 (15)
C6—C5—C4122.01 (16)C28—C27—C26122.06 (16)
C6—C5—H5119.0C28—C27—H27119.0
C4—C5—H5119.0C26—C27—H27119.0
C5—C6—C7116.37 (16)C27—C28—C29116.49 (15)
C5—C6—H6121.8C27—C28—H28121.8
C7—C6—H6121.8C29—C28—H28121.8
O1—C7—C6125.87 (15)O2—C29—C28126.63 (15)
O1—C7—C2110.01 (14)O2—C29—C24109.70 (14)
C6—C7—C2124.07 (16)C28—C29—C24123.67 (15)
C1—C8—O1111.09 (14)C23—C30—O2110.64 (15)
C1—C8—C15134.35 (16)C23—C30—C37134.24 (16)
O1—C8—C15114.57 (14)O2—C30—C37115.11 (14)
C14—C9—C10118.29 (16)C36—C31—C32118.37 (15)
C14—C9—C4121.31 (15)C36—C31—C26121.54 (15)
C10—C9—C4120.40 (15)C32—C31—C26120.09 (15)
C11—C10—C9121.66 (17)C33—C32—C31121.11 (16)
C11—C10—H10119.2C33—C32—H32119.4
C9—C10—H10119.2C31—C32—H32119.4
C12—C11—C10117.74 (17)C34—C33—C32118.24 (16)
C12—C11—H11121.1C34—C33—H33120.9
C10—C11—H11121.1C32—C33—H33120.9
F1—C12—C11118.15 (17)F2—C34—C33118.73 (15)
F1—C12—C13118.64 (17)F2—C34—C35118.38 (16)
C11—C12—C13123.21 (17)C33—C34—C35122.89 (16)
C12—C13—C14118.13 (17)C34—C35—C36118.11 (16)
C12—C13—H13120.9C34—C35—H35120.9
C14—C13—H13120.9C36—C35—H35120.9
C13—C14—C9120.95 (16)C35—C36—C31121.29 (16)
C13—C14—H14119.5C35—C36—H36119.4
C9—C14—H14119.5C31—C36—H36119.4
C20—C15—C16118.55 (15)C42—C37—C38118.26 (16)
C20—C15—C8119.27 (15)C42—C37—C30119.43 (15)
C16—C15—C8122.13 (15)C38—C37—C30122.30 (15)
C17—C16—C15120.54 (16)C39—C38—C37120.69 (17)
C17—C16—H16119.7C39—C38—H38119.7
C15—C16—H16119.7C37—C38—H38119.7
C16—C17—C18121.08 (16)C38—C39—C40121.44 (18)
C16—C17—H17119.5C38—C39—H39119.3
C18—C17—H17119.5C40—C39—H39119.3
C17—C18—C19118.15 (15)C39—C40—C41117.66 (17)
C17—C18—C21120.93 (17)C39—C40—C43120.14 (17)
C19—C18—C21120.91 (16)C41—C40—C43122.20 (17)
C20—C19—C18121.38 (16)C42—C41—C40121.80 (17)
C20—C19—H19119.3C42—C41—H41119.1
C18—C19—H19119.3C40—C41—H41119.1
C19—C20—C15120.30 (16)C41—C42—C37120.14 (17)
C19—C20—H20119.9C41—C42—H42119.9
C15—C20—H20119.9C37—C42—H42119.9
C18—C21—H21A109.5C40—C43—H43A109.5
C18—C21—H21B109.5C40—C43—H43B109.5
H21A—C21—H21B109.5H43A—C43—H43B109.5
C18—C21—H21C109.5C40—C43—H43C109.5
H21A—C21—H21C109.5H43A—C43—H43C109.5
H21B—C21—H21C109.5H43B—C43—H43C109.5
S1—C22—H22A109.5S2—C44—H44A109.5
S1—C22—H22B109.5S2—C44—H44B109.5
H22A—C22—H22B109.5H44A—C44—H44B109.5
S1—C22—H22C109.5S2—C44—H44C109.5
H22A—C22—H22C109.5H44A—C44—H44C109.5
H22B—C22—H22C109.5H44B—C44—H44C109.5
C22—S1—C1—C899.82 (16)C44—S2—C23—C30108.34 (17)
C22—S1—C1—C287.45 (15)C44—S2—C23—C2469.81 (16)
C8—C1—C2—C70.26 (17)C30—C23—C24—C290.09 (18)
S1—C1—C2—C7173.73 (12)S2—C23—C24—C29178.40 (12)
C8—C1—C2—C3175.84 (18)C30—C23—C24—C25178.91 (18)
S1—C1—C2—C31.8 (3)S2—C23—C24—C250.4 (3)
C7—C2—C3—C40.6 (2)C29—C24—C25—C260.7 (2)
C1—C2—C3—C4174.53 (16)C23—C24—C25—C26179.37 (17)
C2—C3—C4—C51.6 (2)C24—C25—C26—C270.6 (2)
C2—C3—C4—C9177.22 (15)C24—C25—C26—C31177.91 (14)
C3—C4—C5—C61.4 (2)C25—C26—C27—C280.4 (2)
C9—C4—C5—C6177.43 (16)C31—C26—C27—C28178.15 (15)
C4—C5—C6—C70.2 (2)C26—C27—C28—C290.2 (2)
C8—O1—C7—C6177.01 (16)C30—O2—C29—C28179.38 (16)
C8—O1—C7—C20.41 (17)C30—O2—C29—C240.46 (17)
C5—C6—C7—O1176.25 (15)C27—C28—C29—O2179.60 (15)
C5—C6—C7—C20.8 (2)C27—C28—C29—C240.2 (2)
C3—C2—C7—O1176.86 (14)C25—C24—C29—O2179.39 (14)
C1—C2—C7—O10.41 (17)C23—C24—C29—O20.34 (17)
C3—C2—C7—C60.6 (2)C25—C24—C29—C280.5 (2)
C1—C2—C7—C6177.06 (15)C23—C24—C29—C28179.51 (15)
C2—C1—C8—O10.02 (18)C24—C23—C30—O20.20 (18)
S1—C1—C8—O1173.89 (11)S2—C23—C30—O2178.61 (12)
C2—C1—C8—C15179.88 (17)C24—C23—C30—C37179.22 (17)
S1—C1—C8—C156.0 (3)S2—C23—C30—C370.8 (3)
C7—O1—C8—C10.24 (18)C29—O2—C30—C230.41 (18)
C7—O1—C8—C15179.66 (13)C29—O2—C30—C37179.13 (13)
C3—C4—C9—C1438.7 (2)C25—C26—C31—C36148.12 (16)
C5—C4—C9—C14142.52 (17)C27—C26—C31—C3633.3 (2)
C3—C4—C9—C10140.75 (17)C25—C26—C31—C3232.8 (2)
C5—C4—C9—C1038.1 (2)C27—C26—C31—C32145.73 (16)
C14—C9—C10—C110.8 (3)C36—C31—C32—C330.6 (2)
C4—C9—C10—C11178.60 (17)C26—C31—C32—C33178.51 (15)
C9—C10—C11—C120.6 (3)C31—C32—C33—C340.4 (2)
C10—C11—C12—F1179.49 (16)C32—C33—C34—F2179.14 (15)
C10—C11—C12—C130.3 (3)C32—C33—C34—C350.2 (3)
F1—C12—C13—C14178.87 (16)F2—C34—C35—C36178.78 (15)
C11—C12—C13—C140.9 (3)C33—C34—C35—C360.5 (3)
C12—C13—C14—C90.6 (3)C34—C35—C36—C310.3 (2)
C10—C9—C14—C130.2 (3)C32—C31—C36—C350.2 (2)
C4—C9—C14—C13179.24 (16)C26—C31—C36—C35178.87 (15)
C1—C8—C15—C20149.90 (19)C23—C30—C37—C42158.75 (18)
O1—C8—C15—C2030.0 (2)O2—C30—C37—C4220.6 (2)
C1—C8—C15—C1632.7 (3)C23—C30—C37—C3822.0 (3)
O1—C8—C15—C16147.39 (15)O2—C30—C37—C38158.57 (15)
C20—C15—C16—C170.5 (2)C42—C37—C38—C390.4 (2)
C8—C15—C16—C17177.92 (15)C30—C37—C38—C39178.86 (16)
C15—C16—C17—C180.1 (3)C37—C38—C39—C400.6 (3)
C16—C17—C18—C190.8 (2)C38—C39—C40—C411.3 (3)
C16—C17—C18—C21178.26 (16)C38—C39—C40—C43178.95 (17)
C17—C18—C19—C200.9 (2)C39—C40—C41—C421.1 (3)
C21—C18—C19—C20178.14 (16)C43—C40—C41—C42179.22 (17)
C18—C19—C20—C150.3 (3)C40—C41—C42—C370.1 (3)
C16—C15—C20—C190.4 (2)C38—C37—C42—C410.6 (2)
C8—C15—C20—C19177.87 (15)C30—C37—C42—C41178.63 (15)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C15–C20 4-methylphenyl ring
D—H···AD—HH···AD···AD—H···A
C28—H28···F2i0.952.433.267 (2)147
C44—H44C···F1ii0.982.523.359 (2)143
C32—H32···Cg1iii0.952.693.465 (2)139
C36—H36···Cg1iv0.952.673.468 (2)143
Symmetry codes: (i) x, y1, z; (ii) x, y1/2, z+1/2; (iii) x, y+1, z; (iv) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C15–C20 4-methylphenyl ring
D—H···AD—HH···AD···AD—H···A
C28—H28···F2i0.952.433.267 (2)147.3
C44—H44C···F1ii0.982.523.359 (2)143.0
C32—H32···Cg1iii0.952.693.465 (2)138.9
C36—H36···Cg1iv0.952.673.468 (2)142.6
Symmetry codes: (i) x, y1, z; (ii) x, y1/2, z+1/2; (iii) x, y+1, z; (iv) x, y+1/2, z1/2.
 

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

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First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o782.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o2742.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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