organic compounds
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
The 22H17FOS, 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.
of the title compound, CCCDC reference: 984666
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2011a,b).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell 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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 984666
10.1107/S1600536814002402/bx2454sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002402/bx2454Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002402/bx2454Isup3.cml
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
(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.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.
Data collection: APEX2 (Bruker, 2009); cell
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).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. | |
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.] | |
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.] |
C22H17FOS | F(000) = 1456 |
Mr = 348.42 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Melting point = 425–426 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 17.897 (6) Å | Cell parameters from 9590 reflections |
b = 10.753 (3) Å | θ = 2.2–26.3° |
c = 17.775 (5) Å | µ = 0.21 mm−1 |
β = 98.541 (18)° | T = 173 K |
V = 3382.8 (18) Å3 | Block, colourless |
Z = 8 | 0.43 × 0.36 × 0.12 mm |
Bruker SMART APEXII CCD diffractometer | 7388 independent reflections |
Radiation source: rotating anode | 5723 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.051 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 2.2° |
φ and ω scans | h = −22→22 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −13→13 |
Tmin = 0.681, Tmax = 0.746 | l = −22→22 |
55108 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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.114 | H-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 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C22H17FOS | V = 3382.8 (18) Å3 |
Mr = 348.42 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.897 (6) Å | µ = 0.21 mm−1 |
b = 10.753 (3) Å | T = 173 K |
c = 17.775 (5) Å | 0.43 × 0.36 × 0.12 mm |
β = 98.541 (18)° |
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 = 0.746 | Rint = 0.051 |
55108 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.33 e Å−3 |
7388 reflections | Δρmin = −0.37 e Å−3 |
454 parameters |
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 | ||
S1 | 0.37299 (2) | 0.21067 (4) | 0.29473 (2) | 0.02650 (11) | |
F1 | 0.06413 (7) | 0.84290 (10) | 0.44228 (7) | 0.0486 (3) | |
O1 | 0.23646 (6) | −0.00311 (10) | 0.39568 (7) | 0.0263 (3) | |
C1 | 0.30874 (9) | 0.14077 (15) | 0.34763 (9) | 0.0237 (3) | |
C2 | 0.25213 (9) | 0.20428 (15) | 0.38362 (9) | 0.0241 (3) | |
C3 | 0.23108 (9) | 0.32782 (15) | 0.39093 (9) | 0.0252 (4) | |
H3 | 0.2594 | 0.3931 | 0.3728 | 0.030* | |
C4 | 0.16752 (9) | 0.35447 (15) | 0.42539 (9) | 0.0262 (4) | |
C5 | 0.12703 (10) | 0.25676 (16) | 0.45380 (10) | 0.0290 (4) | |
H5 | 0.0847 | 0.2763 | 0.4781 | 0.035* | |
C6 | 0.14701 (10) | 0.13436 (16) | 0.44740 (10) | 0.0288 (4) | |
H6 | 0.1196 | 0.0688 | 0.4664 | 0.035* | |
C7 | 0.20949 (9) | 0.11165 (15) | 0.41162 (9) | 0.0253 (4) | |
C8 | 0.29684 (9) | 0.01726 (15) | 0.35648 (9) | 0.0241 (3) | |
C9 | 0.14098 (9) | 0.48411 (15) | 0.43128 (9) | 0.0261 (4) | |
C10 | 0.06343 (10) | 0.51114 (17) | 0.42028 (10) | 0.0316 (4) | |
H10 | 0.0281 | 0.4451 | 0.4101 | 0.038* | |
C11 | 0.03721 (10) | 0.63092 (18) | 0.42381 (10) | 0.0352 (4) | |
H11 | −0.0154 | 0.6485 | 0.4158 | 0.042* | |
C12 | 0.08954 (11) | 0.72404 (16) | 0.43927 (10) | 0.0336 (4) | |
C13 | 0.16654 (11) | 0.70297 (17) | 0.45160 (10) | 0.0327 (4) | |
H13 | 0.2012 | 0.7697 | 0.4629 | 0.039* | |
C14 | 0.19175 (10) | 0.58206 (16) | 0.44707 (10) | 0.0293 (4) | |
H14 | 0.2445 | 0.5656 | 0.4548 | 0.035* | |
C15 | 0.33306 (9) | −0.09598 (15) | 0.33398 (9) | 0.0246 (3) | |
C16 | 0.41086 (9) | −0.10156 (16) | 0.32995 (9) | 0.0274 (4) | |
H16 | 0.4412 | −0.0293 | 0.3405 | 0.033* | |
C17 | 0.44362 (10) | −0.21136 (16) | 0.31081 (9) | 0.0286 (4) | |
H17 | 0.4963 | −0.2135 | 0.3084 | 0.034* | |
C18 | 0.40082 (10) | −0.31842 (15) | 0.29508 (9) | 0.0277 (4) | |
C19 | 0.32341 (10) | −0.31272 (15) | 0.30001 (9) | 0.0277 (4) | |
H19 | 0.2934 | −0.3854 | 0.2901 | 0.033* | |
C20 | 0.28997 (10) | −0.20375 (15) | 0.31890 (9) | 0.0265 (4) | |
H20 | 0.2374 | −0.2021 | 0.3217 | 0.032* | |
C21 | 0.43623 (11) | −0.43679 (17) | 0.27212 (11) | 0.0371 (4) | |
H21A | 0.4764 | −0.4628 | 0.3127 | 0.045* | |
H21B | 0.4577 | −0.4226 | 0.2252 | 0.045* | |
H21C | 0.3977 | −0.5020 | 0.2635 | 0.045* | |
C22 | 0.45009 (10) | 0.24833 (18) | 0.36934 (11) | 0.0375 (4) | |
H22A | 0.4314 | 0.3014 | 0.4073 | 0.056* | |
H22B | 0.4896 | 0.2925 | 0.3474 | 0.056* | |
H22C | 0.4710 | 0.1715 | 0.3936 | 0.056* | |
S2 | 0.12675 (3) | 0.49163 (4) | 0.20081 (3) | 0.03560 (13) | |
F2 | 0.41994 (6) | 1.12966 (9) | 0.04363 (7) | 0.0422 (3) | |
O2 | 0.27237 (6) | 0.27471 (10) | 0.11261 (6) | 0.0262 (3) | |
C23 | 0.19837 (9) | 0.41799 (16) | 0.15898 (9) | 0.0270 (4) | |
C24 | 0.25573 (9) | 0.48150 (15) | 0.12453 (9) | 0.0256 (4) | |
C25 | 0.27344 (9) | 0.60571 (15) | 0.11360 (9) | 0.0253 (3) | |
H25 | 0.2442 | 0.6701 | 0.1315 | 0.030* | |
C26 | 0.33444 (9) | 0.63484 (15) | 0.07614 (9) | 0.0239 (3) | |
C27 | 0.37678 (9) | 0.53799 (16) | 0.04921 (10) | 0.0267 (4) | |
H27 | 0.4180 | 0.5587 | 0.0235 | 0.032* | |
C28 | 0.36017 (9) | 0.41427 (15) | 0.05910 (10) | 0.0274 (4) | |
H28 | 0.3889 | 0.3495 | 0.0410 | 0.033* | |
C29 | 0.29921 (9) | 0.38949 (15) | 0.09688 (9) | 0.0249 (4) | |
C30 | 0.21047 (9) | 0.29419 (15) | 0.15035 (9) | 0.0252 (3) | |
C31 | 0.35593 (9) | 0.76637 (15) | 0.06618 (9) | 0.0232 (3) | |
C32 | 0.34603 (9) | 0.85462 (15) | 0.12153 (9) | 0.0259 (4) | |
H32 | 0.3243 | 0.8300 | 0.1649 | 0.031* | |
C33 | 0.36720 (9) | 0.97693 (15) | 0.11432 (10) | 0.0277 (4) | |
H33 | 0.3607 | 1.0366 | 0.1522 | 0.033* | |
C34 | 0.39803 (10) | 1.01017 (15) | 0.05080 (10) | 0.0291 (4) | |
C35 | 0.40837 (9) | 0.92699 (16) | −0.00564 (10) | 0.0282 (4) | |
H35 | 0.4294 | 0.9529 | −0.0491 | 0.034* | |
C36 | 0.38730 (9) | 0.80506 (15) | 0.00268 (9) | 0.0254 (3) | |
H36 | 0.3942 | 0.7462 | −0.0355 | 0.030* | |
C37 | 0.17303 (9) | 0.18137 (15) | 0.17111 (9) | 0.0251 (4) | |
C38 | 0.12785 (10) | 0.17959 (17) | 0.22887 (10) | 0.0312 (4) | |
H38 | 0.1201 | 0.2542 | 0.2553 | 0.037* | |
C39 | 0.09441 (10) | 0.07072 (17) | 0.24784 (10) | 0.0335 (4) | |
H39 | 0.0635 | 0.0718 | 0.2869 | 0.040* | |
C40 | 0.10489 (10) | −0.04023 (17) | 0.21115 (10) | 0.0308 (4) | |
C41 | 0.14927 (10) | −0.03773 (17) | 0.15302 (11) | 0.0336 (4) | |
H41 | 0.1565 | −0.1124 | 0.1265 | 0.040* | |
C42 | 0.18297 (10) | 0.07025 (16) | 0.13297 (10) | 0.0291 (4) | |
H42 | 0.2130 | 0.0691 | 0.0932 | 0.035* | |
C43 | 0.06869 (12) | −0.15786 (18) | 0.23410 (12) | 0.0441 (5) | |
H43A | 0.0526 | −0.1461 | 0.2840 | 0.066* | |
H43B | 0.1052 | −0.2262 | 0.2370 | 0.066* | |
H43C | 0.0247 | −0.1779 | 0.1963 | 0.066* | |
C44 | 0.07083 (11) | 0.5533 (2) | 0.11587 (12) | 0.0441 (5) | |
H44A | 0.1030 | 0.6040 | 0.0879 | 0.066* | |
H44B | 0.0300 | 0.6048 | 0.1301 | 0.066* | |
H44C | 0.0492 | 0.4845 | 0.0836 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0272 (2) | 0.0265 (2) | 0.0265 (2) | −0.00032 (16) | 0.00621 (17) | 0.00148 (16) |
F1 | 0.0554 (7) | 0.0297 (6) | 0.0587 (7) | 0.0154 (5) | 0.0019 (6) | −0.0058 (5) |
O1 | 0.0268 (6) | 0.0222 (6) | 0.0312 (6) | 0.0011 (5) | 0.0085 (5) | 0.0004 (5) |
C1 | 0.0223 (8) | 0.0247 (8) | 0.0241 (8) | 0.0011 (6) | 0.0030 (7) | 0.0004 (6) |
C2 | 0.0218 (8) | 0.0268 (8) | 0.0231 (8) | 0.0006 (6) | 0.0015 (7) | 0.0004 (6) |
C3 | 0.0233 (8) | 0.0236 (8) | 0.0284 (8) | −0.0006 (6) | 0.0030 (7) | −0.0016 (7) |
C4 | 0.0235 (8) | 0.0273 (9) | 0.0270 (8) | 0.0012 (7) | 0.0007 (7) | −0.0032 (7) |
C5 | 0.0250 (9) | 0.0325 (9) | 0.0304 (9) | 0.0001 (7) | 0.0072 (7) | −0.0045 (7) |
C6 | 0.0288 (9) | 0.0295 (9) | 0.0294 (9) | −0.0024 (7) | 0.0083 (7) | −0.0007 (7) |
C7 | 0.0260 (9) | 0.0239 (8) | 0.0255 (8) | 0.0020 (6) | 0.0024 (7) | −0.0014 (6) |
C8 | 0.0223 (8) | 0.0262 (8) | 0.0237 (8) | 0.0010 (6) | 0.0031 (7) | 0.0008 (6) |
C9 | 0.0259 (9) | 0.0284 (9) | 0.0241 (8) | 0.0029 (7) | 0.0039 (7) | −0.0034 (7) |
C10 | 0.0257 (9) | 0.0336 (10) | 0.0347 (9) | 0.0004 (7) | 0.0012 (8) | −0.0065 (8) |
C11 | 0.0263 (9) | 0.0403 (11) | 0.0377 (10) | 0.0094 (8) | 0.0010 (8) | −0.0056 (8) |
C12 | 0.0430 (11) | 0.0281 (9) | 0.0290 (9) | 0.0099 (8) | 0.0032 (8) | −0.0026 (7) |
C13 | 0.0367 (10) | 0.0283 (9) | 0.0332 (9) | −0.0023 (8) | 0.0051 (8) | −0.0024 (7) |
C14 | 0.0259 (9) | 0.0297 (9) | 0.0322 (9) | 0.0016 (7) | 0.0044 (7) | −0.0006 (7) |
C15 | 0.0276 (9) | 0.0237 (8) | 0.0226 (8) | 0.0024 (7) | 0.0038 (7) | 0.0025 (6) |
C16 | 0.0284 (9) | 0.0252 (8) | 0.0288 (9) | −0.0007 (7) | 0.0045 (7) | 0.0014 (7) |
C17 | 0.0271 (9) | 0.0305 (9) | 0.0286 (9) | 0.0037 (7) | 0.0056 (7) | 0.0025 (7) |
C18 | 0.0352 (9) | 0.0248 (8) | 0.0233 (8) | 0.0058 (7) | 0.0050 (7) | 0.0031 (7) |
C19 | 0.0350 (10) | 0.0237 (8) | 0.0240 (8) | −0.0019 (7) | 0.0027 (7) | 0.0010 (7) |
C20 | 0.0256 (8) | 0.0274 (9) | 0.0263 (8) | −0.0003 (7) | 0.0033 (7) | 0.0011 (7) |
C21 | 0.0443 (11) | 0.0298 (10) | 0.0382 (10) | 0.0089 (8) | 0.0093 (9) | −0.0009 (8) |
C22 | 0.0319 (10) | 0.0365 (10) | 0.0427 (11) | −0.0060 (8) | 0.0009 (8) | 0.0003 (8) |
S2 | 0.0374 (3) | 0.0324 (3) | 0.0401 (3) | 0.00336 (19) | 0.0163 (2) | −0.00116 (19) |
F2 | 0.0504 (7) | 0.0216 (5) | 0.0580 (7) | −0.0052 (5) | 0.0193 (6) | −0.0003 (5) |
O2 | 0.0250 (6) | 0.0221 (6) | 0.0318 (6) | −0.0013 (4) | 0.0056 (5) | −0.0007 (5) |
C23 | 0.0267 (9) | 0.0274 (9) | 0.0271 (8) | −0.0001 (7) | 0.0048 (7) | −0.0018 (7) |
C24 | 0.0245 (8) | 0.0268 (9) | 0.0251 (8) | 0.0006 (7) | 0.0023 (7) | −0.0012 (7) |
C25 | 0.0252 (8) | 0.0237 (8) | 0.0269 (8) | 0.0012 (6) | 0.0036 (7) | −0.0022 (7) |
C26 | 0.0240 (8) | 0.0233 (8) | 0.0230 (8) | −0.0007 (6) | −0.0007 (7) | −0.0014 (6) |
C27 | 0.0239 (8) | 0.0271 (9) | 0.0295 (9) | −0.0015 (7) | 0.0050 (7) | −0.0019 (7) |
C28 | 0.0257 (9) | 0.0247 (9) | 0.0321 (9) | 0.0026 (7) | 0.0054 (7) | −0.0035 (7) |
C29 | 0.0250 (8) | 0.0218 (8) | 0.0270 (8) | −0.0013 (6) | 0.0010 (7) | −0.0010 (6) |
C30 | 0.0215 (8) | 0.0294 (9) | 0.0243 (8) | −0.0003 (7) | 0.0019 (7) | −0.0022 (7) |
C31 | 0.0191 (8) | 0.0232 (8) | 0.0259 (8) | 0.0007 (6) | −0.0010 (6) | −0.0001 (6) |
C32 | 0.0257 (9) | 0.0262 (9) | 0.0259 (8) | 0.0012 (7) | 0.0040 (7) | 0.0002 (7) |
C33 | 0.0282 (9) | 0.0243 (8) | 0.0303 (9) | 0.0019 (7) | 0.0038 (7) | −0.0054 (7) |
C34 | 0.0269 (9) | 0.0213 (8) | 0.0387 (10) | −0.0021 (7) | 0.0033 (8) | 0.0021 (7) |
C35 | 0.0261 (9) | 0.0307 (9) | 0.0283 (9) | −0.0012 (7) | 0.0059 (7) | 0.0024 (7) |
C36 | 0.0240 (8) | 0.0269 (8) | 0.0250 (8) | 0.0012 (7) | 0.0026 (7) | −0.0027 (7) |
C37 | 0.0226 (8) | 0.0267 (8) | 0.0248 (8) | −0.0005 (6) | −0.0005 (7) | 0.0014 (7) |
C38 | 0.0336 (10) | 0.0313 (9) | 0.0282 (9) | −0.0034 (7) | 0.0028 (8) | −0.0047 (7) |
C39 | 0.0337 (10) | 0.0392 (10) | 0.0286 (9) | −0.0036 (8) | 0.0075 (8) | 0.0011 (8) |
C40 | 0.0300 (9) | 0.0298 (9) | 0.0316 (9) | −0.0020 (7) | 0.0005 (7) | 0.0068 (7) |
C41 | 0.0346 (10) | 0.0250 (9) | 0.0413 (10) | 0.0013 (7) | 0.0063 (8) | −0.0005 (8) |
C42 | 0.0282 (9) | 0.0280 (9) | 0.0320 (9) | 0.0012 (7) | 0.0076 (7) | 0.0010 (7) |
C43 | 0.0476 (12) | 0.0358 (11) | 0.0505 (12) | −0.0039 (9) | 0.0120 (10) | 0.0113 (9) |
C44 | 0.0317 (10) | 0.0470 (12) | 0.0538 (13) | 0.0058 (9) | 0.0065 (9) | −0.0034 (10) |
S1—C1 | 1.7586 (17) | S2—C23 | 1.7623 (18) |
S1—C22 | 1.8119 (19) | S2—C44 | 1.809 (2) |
F1—C12 | 1.360 (2) | F2—C34 | 1.3550 (19) |
O1—C7 | 1.3699 (19) | O2—C29 | 1.3683 (19) |
O1—C8 | 1.388 (2) | O2—C30 | 1.393 (2) |
C1—C8 | 1.358 (2) | C23—C30 | 1.361 (2) |
C1—C2 | 1.447 (2) | C23—C24 | 1.443 (2) |
C2—C7 | 1.391 (2) | C24—C29 | 1.393 (2) |
C2—C3 | 1.392 (2) | C24—C25 | 1.393 (2) |
C3—C4 | 1.399 (2) | C25—C26 | 1.396 (2) |
C3—H3 | 0.9500 | C25—H25 | 0.9500 |
C4—C5 | 1.412 (2) | C26—C27 | 1.413 (2) |
C4—C9 | 1.481 (2) | C26—C31 | 1.483 (2) |
C5—C6 | 1.373 (2) | C27—C28 | 1.380 (2) |
C5—H5 | 0.9500 | C27—H27 | 0.9500 |
C6—C7 | 1.388 (2) | C28—C29 | 1.389 (2) |
C6—H6 | 0.9500 | C28—H28 | 0.9500 |
C8—C15 | 1.463 (2) | C30—C37 | 1.460 (2) |
C9—C14 | 1.392 (2) | C31—C36 | 1.397 (2) |
C9—C10 | 1.403 (2) | C31—C32 | 1.397 (2) |
C10—C11 | 1.375 (3) | C32—C33 | 1.380 (2) |
C10—H10 | 0.9500 | C32—H32 | 0.9500 |
C11—C12 | 1.371 (3) | C33—C34 | 1.375 (3) |
C11—H11 | 0.9500 | C33—H33 | 0.9500 |
C12—C13 | 1.382 (3) | C34—C35 | 1.377 (2) |
C13—C14 | 1.382 (2) | C35—C36 | 1.378 (2) |
C13—H13 | 0.9500 | C35—H35 | 0.9500 |
C14—H14 | 0.9500 | C36—H36 | 0.9500 |
C15—C20 | 1.396 (2) | C37—C42 | 1.398 (2) |
C15—C16 | 1.406 (2) | C37—C38 | 1.398 (2) |
C16—C17 | 1.383 (2) | C38—C39 | 1.379 (3) |
C16—H16 | 0.9500 | C38—H38 | 0.9500 |
C17—C18 | 1.388 (2) | C39—C40 | 1.386 (3) |
C17—H17 | 0.9500 | C39—H39 | 0.9500 |
C18—C19 | 1.402 (3) | C40—C41 | 1.394 (3) |
C18—C21 | 1.505 (2) | C40—C43 | 1.505 (3) |
C19—C20 | 1.380 (2) | C41—C42 | 1.379 (2) |
C19—H19 | 0.9500 | C41—H41 | 0.9500 |
C20—H20 | 0.9500 | C42—H42 | 0.9500 |
C21—H21A | 0.9800 | C43—H43A | 0.9800 |
C21—H21B | 0.9800 | C43—H43B | 0.9800 |
C21—H21C | 0.9800 | C43—H43C | 0.9800 |
C22—H22A | 0.9800 | C44—H44A | 0.9800 |
C22—H22B | 0.9800 | C44—H44B | 0.9800 |
C22—H22C | 0.9800 | C44—H44C | 0.9800 |
C1—S1—C22 | 101.05 (9) | C23—S2—C44 | 99.18 (9) |
C7—O1—C8 | 106.64 (12) | C29—O2—C30 | 106.93 (12) |
C8—C1—C2 | 106.15 (14) | C30—C23—C24 | 106.25 (15) |
C8—C1—S1 | 127.32 (13) | C30—C23—S2 | 128.68 (14) |
C2—C1—S1 | 126.22 (12) | C24—C23—S2 | 125.05 (13) |
C7—C2—C3 | 118.64 (15) | C29—C24—C25 | 118.77 (16) |
C7—C2—C1 | 106.11 (14) | C29—C24—C23 | 106.47 (15) |
C3—C2—C1 | 135.11 (16) | C25—C24—C23 | 134.74 (16) |
C2—C3—C4 | 119.02 (16) | C24—C25—C26 | 119.46 (15) |
C2—C3—H3 | 120.5 | C24—C25—H25 | 120.3 |
C4—C3—H3 | 120.5 | C26—C25—H25 | 120.3 |
C3—C4—C5 | 119.87 (15) | C25—C26—C27 | 119.54 (15) |
C3—C4—C9 | 120.91 (15) | C25—C26—C31 | 120.39 (15) |
C5—C4—C9 | 119.21 (15) | C27—C26—C31 | 120.05 (15) |
C6—C5—C4 | 122.01 (16) | C28—C27—C26 | 122.06 (16) |
C6—C5—H5 | 119.0 | C28—C27—H27 | 119.0 |
C4—C5—H5 | 119.0 | C26—C27—H27 | 119.0 |
C5—C6—C7 | 116.37 (16) | C27—C28—C29 | 116.49 (15) |
C5—C6—H6 | 121.8 | C27—C28—H28 | 121.8 |
C7—C6—H6 | 121.8 | C29—C28—H28 | 121.8 |
O1—C7—C6 | 125.87 (15) | O2—C29—C28 | 126.63 (15) |
O1—C7—C2 | 110.01 (14) | O2—C29—C24 | 109.70 (14) |
C6—C7—C2 | 124.07 (16) | C28—C29—C24 | 123.67 (15) |
C1—C8—O1 | 111.09 (14) | C23—C30—O2 | 110.64 (15) |
C1—C8—C15 | 134.35 (16) | C23—C30—C37 | 134.24 (16) |
O1—C8—C15 | 114.57 (14) | O2—C30—C37 | 115.11 (14) |
C14—C9—C10 | 118.29 (16) | C36—C31—C32 | 118.37 (15) |
C14—C9—C4 | 121.31 (15) | C36—C31—C26 | 121.54 (15) |
C10—C9—C4 | 120.40 (15) | C32—C31—C26 | 120.09 (15) |
C11—C10—C9 | 121.66 (17) | C33—C32—C31 | 121.11 (16) |
C11—C10—H10 | 119.2 | C33—C32—H32 | 119.4 |
C9—C10—H10 | 119.2 | C31—C32—H32 | 119.4 |
C12—C11—C10 | 117.74 (17) | C34—C33—C32 | 118.24 (16) |
C12—C11—H11 | 121.1 | C34—C33—H33 | 120.9 |
C10—C11—H11 | 121.1 | C32—C33—H33 | 120.9 |
F1—C12—C11 | 118.15 (17) | F2—C34—C33 | 118.73 (15) |
F1—C12—C13 | 118.64 (17) | F2—C34—C35 | 118.38 (16) |
C11—C12—C13 | 123.21 (17) | C33—C34—C35 | 122.89 (16) |
C12—C13—C14 | 118.13 (17) | C34—C35—C36 | 118.11 (16) |
C12—C13—H13 | 120.9 | C34—C35—H35 | 120.9 |
C14—C13—H13 | 120.9 | C36—C35—H35 | 120.9 |
C13—C14—C9 | 120.95 (16) | C35—C36—C31 | 121.29 (16) |
C13—C14—H14 | 119.5 | C35—C36—H36 | 119.4 |
C9—C14—H14 | 119.5 | C31—C36—H36 | 119.4 |
C20—C15—C16 | 118.55 (15) | C42—C37—C38 | 118.26 (16) |
C20—C15—C8 | 119.27 (15) | C42—C37—C30 | 119.43 (15) |
C16—C15—C8 | 122.13 (15) | C38—C37—C30 | 122.30 (15) |
C17—C16—C15 | 120.54 (16) | C39—C38—C37 | 120.69 (17) |
C17—C16—H16 | 119.7 | C39—C38—H38 | 119.7 |
C15—C16—H16 | 119.7 | C37—C38—H38 | 119.7 |
C16—C17—C18 | 121.08 (16) | C38—C39—C40 | 121.44 (18) |
C16—C17—H17 | 119.5 | C38—C39—H39 | 119.3 |
C18—C17—H17 | 119.5 | C40—C39—H39 | 119.3 |
C17—C18—C19 | 118.15 (15) | C39—C40—C41 | 117.66 (17) |
C17—C18—C21 | 120.93 (17) | C39—C40—C43 | 120.14 (17) |
C19—C18—C21 | 120.91 (16) | C41—C40—C43 | 122.20 (17) |
C20—C19—C18 | 121.38 (16) | C42—C41—C40 | 121.80 (17) |
C20—C19—H19 | 119.3 | C42—C41—H41 | 119.1 |
C18—C19—H19 | 119.3 | C40—C41—H41 | 119.1 |
C19—C20—C15 | 120.30 (16) | C41—C42—C37 | 120.14 (17) |
C19—C20—H20 | 119.9 | C41—C42—H42 | 119.9 |
C15—C20—H20 | 119.9 | C37—C42—H42 | 119.9 |
C18—C21—H21A | 109.5 | C40—C43—H43A | 109.5 |
C18—C21—H21B | 109.5 | C40—C43—H43B | 109.5 |
H21A—C21—H21B | 109.5 | H43A—C43—H43B | 109.5 |
C18—C21—H21C | 109.5 | C40—C43—H43C | 109.5 |
H21A—C21—H21C | 109.5 | H43A—C43—H43C | 109.5 |
H21B—C21—H21C | 109.5 | H43B—C43—H43C | 109.5 |
S1—C22—H22A | 109.5 | S2—C44—H44A | 109.5 |
S1—C22—H22B | 109.5 | S2—C44—H44B | 109.5 |
H22A—C22—H22B | 109.5 | H44A—C44—H44B | 109.5 |
S1—C22—H22C | 109.5 | S2—C44—H44C | 109.5 |
H22A—C22—H22C | 109.5 | H44A—C44—H44C | 109.5 |
H22B—C22—H22C | 109.5 | H44B—C44—H44C | 109.5 |
C22—S1—C1—C8 | −99.82 (16) | C44—S2—C23—C30 | −108.34 (17) |
C22—S1—C1—C2 | 87.45 (15) | C44—S2—C23—C24 | 69.81 (16) |
C8—C1—C2—C7 | −0.26 (17) | C30—C23—C24—C29 | 0.09 (18) |
S1—C1—C2—C7 | 173.73 (12) | S2—C23—C24—C29 | −178.40 (12) |
C8—C1—C2—C3 | −175.84 (18) | C30—C23—C24—C25 | 178.91 (18) |
S1—C1—C2—C3 | −1.8 (3) | S2—C23—C24—C25 | 0.4 (3) |
C7—C2—C3—C4 | −0.6 (2) | C29—C24—C25—C26 | −0.7 (2) |
C1—C2—C3—C4 | 174.53 (16) | C23—C24—C25—C26 | −179.37 (17) |
C2—C3—C4—C5 | 1.6 (2) | C24—C25—C26—C27 | 0.6 (2) |
C2—C3—C4—C9 | −177.22 (15) | C24—C25—C26—C31 | −177.91 (14) |
C3—C4—C5—C6 | −1.4 (2) | C25—C26—C27—C28 | −0.4 (2) |
C9—C4—C5—C6 | 177.43 (16) | C31—C26—C27—C28 | 178.15 (15) |
C4—C5—C6—C7 | 0.2 (2) | C26—C27—C28—C29 | 0.2 (2) |
C8—O1—C7—C6 | 177.01 (16) | C30—O2—C29—C28 | −179.38 (16) |
C8—O1—C7—C2 | −0.41 (17) | C30—O2—C29—C24 | 0.46 (17) |
C5—C6—C7—O1 | −176.25 (15) | C27—C28—C29—O2 | 179.60 (15) |
C5—C6—C7—C2 | 0.8 (2) | C27—C28—C29—C24 | −0.2 (2) |
C3—C2—C7—O1 | 176.86 (14) | C25—C24—C29—O2 | −179.39 (14) |
C1—C2—C7—O1 | 0.41 (17) | C23—C24—C29—O2 | −0.34 (17) |
C3—C2—C7—C6 | −0.6 (2) | C25—C24—C29—C28 | 0.5 (2) |
C1—C2—C7—C6 | −177.06 (15) | C23—C24—C29—C28 | 179.51 (15) |
C2—C1—C8—O1 | 0.02 (18) | C24—C23—C30—O2 | 0.20 (18) |
S1—C1—C8—O1 | −173.89 (11) | S2—C23—C30—O2 | 178.61 (12) |
C2—C1—C8—C15 | 179.88 (17) | C24—C23—C30—C37 | −179.22 (17) |
S1—C1—C8—C15 | 6.0 (3) | S2—C23—C30—C37 | −0.8 (3) |
C7—O1—C8—C1 | 0.24 (18) | C29—O2—C30—C23 | −0.41 (18) |
C7—O1—C8—C15 | −179.66 (13) | C29—O2—C30—C37 | 179.13 (13) |
C3—C4—C9—C14 | −38.7 (2) | C25—C26—C31—C36 | −148.12 (16) |
C5—C4—C9—C14 | 142.52 (17) | C27—C26—C31—C36 | 33.3 (2) |
C3—C4—C9—C10 | 140.75 (17) | C25—C26—C31—C32 | 32.8 (2) |
C5—C4—C9—C10 | −38.1 (2) | C27—C26—C31—C32 | −145.73 (16) |
C14—C9—C10—C11 | 0.8 (3) | C36—C31—C32—C33 | −0.6 (2) |
C4—C9—C10—C11 | −178.60 (17) | C26—C31—C32—C33 | 178.51 (15) |
C9—C10—C11—C12 | −0.6 (3) | C31—C32—C33—C34 | 0.4 (2) |
C10—C11—C12—F1 | 179.49 (16) | C32—C33—C34—F2 | −179.14 (15) |
C10—C11—C12—C13 | −0.3 (3) | C32—C33—C34—C35 | 0.2 (3) |
F1—C12—C13—C14 | −178.87 (16) | F2—C34—C35—C36 | 178.78 (15) |
C11—C12—C13—C14 | 0.9 (3) | C33—C34—C35—C36 | −0.5 (3) |
C12—C13—C14—C9 | −0.6 (3) | C34—C35—C36—C31 | 0.3 (2) |
C10—C9—C14—C13 | −0.2 (3) | C32—C31—C36—C35 | 0.2 (2) |
C4—C9—C14—C13 | 179.24 (16) | C26—C31—C36—C35 | −178.87 (15) |
C1—C8—C15—C20 | −149.90 (19) | C23—C30—C37—C42 | 158.75 (18) |
O1—C8—C15—C20 | 30.0 (2) | O2—C30—C37—C42 | −20.6 (2) |
C1—C8—C15—C16 | 32.7 (3) | C23—C30—C37—C38 | −22.0 (3) |
O1—C8—C15—C16 | −147.39 (15) | O2—C30—C37—C38 | 158.57 (15) |
C20—C15—C16—C17 | 0.5 (2) | C42—C37—C38—C39 | 0.4 (2) |
C8—C15—C16—C17 | 177.92 (15) | C30—C37—C38—C39 | −178.86 (16) |
C15—C16—C17—C18 | 0.1 (3) | C37—C38—C39—C40 | 0.6 (3) |
C16—C17—C18—C19 | −0.8 (2) | C38—C39—C40—C41 | −1.3 (3) |
C16—C17—C18—C21 | 178.26 (16) | C38—C39—C40—C43 | 178.95 (17) |
C17—C18—C19—C20 | 0.9 (2) | C39—C40—C41—C42 | 1.1 (3) |
C21—C18—C19—C20 | −178.14 (16) | C43—C40—C41—C42 | −179.22 (17) |
C18—C19—C20—C15 | −0.3 (3) | C40—C41—C42—C37 | −0.1 (3) |
C16—C15—C20—C19 | −0.4 (2) | C38—C37—C42—C41 | −0.6 (2) |
C8—C15—C20—C19 | −177.87 (15) | C30—C37—C42—C41 | 178.63 (15) |
Cg1 is the centroid of the C15–C20 4-methylphenyl ring |
D—H···A | D—H | H···A | D···A | 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−1/2, −z+1/2; (iii) x, y+1, z; (iv) x, −y+1/2, z−1/2. |
Cg1 is the centroid of the C15–C20 4-methylphenyl ring |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28···F2i | 0.95 | 2.43 | 3.267 (2) | 147.3 |
C44—H44C···F1ii | 0.98 | 2.52 | 3.359 (2) | 143.0 |
C32—H32···Cg1iii | 0.95 | 2.69 | 3.465 (2) | 138.9 |
C36—H36···Cg1iv | 0.95 | 2.67 | 3.468 (2) | 142.6 |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1/2, −z+1/2; (iii) x, y+1, z; (iv) x, −y+1/2, z−1/2. |
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
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o2742. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.