organic compounds
2-(4-Fluorophenyl)-5-iodo-3-isopropylsulfonyl-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
There are two symmetry-independent molecules, A and B, in the of the title compound, C17H14FIO3S. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane [r.m.s. deviation = 0.013 (2) Å in molecule A and 0.016 (2) Å in molecule B] of the benzofuran fragment is 57.71 (7)° in molecule A and 44.95 (7)° in molecule B. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and I⋯O contacts [I⋯O = 3.3646 (15) and 3.2354 (14) Å], forming a three--dimensional network.
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b). For a review of halogen bonding, see: Politzer et al. (2007).
Experimental
Crystal data
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Refinement
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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 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812043218/ld2079sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043218/ld2079Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812043218/ld2079Isup3.cml
3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-isopropylsulfanyl-1-benzofuran (330 mg, 0.8 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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
(benzene) to afford the title compound as a colorless solid [yield 72%, m.p. 422–423 K; Rf = 0.65 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.All H atoms were geometrically positioned and refined using a riding model, with C—H = 0.95 Å for aryl, 1.00 Å for methine and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methine, 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 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C17H14FIO3S | Z = 4 |
Mr = 444.24 | F(000) = 872 |
Triclinic, P1 | Dx = 1.797 Mg m−3 |
Hall symbol: -P 1 | Melting point: 422.5 K |
a = 11.7419 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.8226 (2) Å | Cell parameters from 9874 reflections |
c = 12.8474 (2) Å | θ = 2.5–28.3° |
α = 66.576 (1)° | µ = 2.10 mm−1 |
β = 82.703 (1)° | T = 173 K |
γ = 67.769 (1)° | Block, colourless |
V = 1642.36 (5) Å3 | 0.31 × 0.22 × 0.22 mm |
Bruker SMART APEXII CCD diffractometer | 8149 independent reflections |
Radiation source: rotating anode | 7224 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.031 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
ϕ and ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −17→16 |
Tmin = 0.594, Tmax = 0.746 | l = −17→17 |
30779 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)] = 0.025 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0258P)2 + 0.967P] where P = (Fo2 + 2Fc2)/3 |
8149 reflections | (Δ/σ)max = 0.001 |
419 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.88 e Å−3 |
C17H14FIO3S | γ = 67.769 (1)° |
Mr = 444.24 | V = 1642.36 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.7419 (2) Å | Mo Kα radiation |
b = 12.8226 (2) Å | µ = 2.10 mm−1 |
c = 12.8474 (2) Å | T = 173 K |
α = 66.576 (1)° | 0.31 × 0.22 × 0.22 mm |
β = 82.703 (1)° |
Bruker SMART APEXII CCD diffractometer | 8149 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 7224 reflections with I > 2σ(I) |
Tmin = 0.594, Tmax = 0.746 | Rint = 0.031 |
30779 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.65 e Å−3 |
8149 reflections | Δρmin = −0.88 e Å−3 |
419 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 | ||
I1 | 0.326089 (13) | 0.662386 (14) | 0.466164 (12) | 0.03553 (5) | |
I2 | 0.737096 (13) | 0.416299 (14) | −0.189163 (12) | 0.03660 (5) | |
S1 | 0.88239 (4) | 0.60922 (4) | 0.32898 (4) | 0.02482 (10) | |
S2 | 0.54126 (4) | 0.09203 (4) | 0.24522 (4) | 0.02417 (10) | |
F1 | 1.12323 (18) | 0.8849 (3) | −0.18380 (15) | 0.0963 (8) | |
F2 | −0.06003 (14) | 0.13892 (15) | 0.42793 (13) | 0.0525 (4) | |
O1 | 0.64958 (12) | 0.85328 (12) | 0.07633 (11) | 0.0260 (3) | |
O2 | 0.84377 (14) | 0.51275 (13) | 0.40782 (13) | 0.0352 (3) | |
O3 | 0.99193 (13) | 0.57644 (13) | 0.26654 (13) | 0.0328 (3) | |
O4 | 0.26036 (12) | 0.35894 (13) | 0.04663 (12) | 0.0274 (3) | |
O5 | 0.64518 (14) | 0.04309 (14) | 0.18388 (13) | 0.0350 (3) | |
O6 | 0.48419 (14) | 0.01133 (14) | 0.32324 (13) | 0.0342 (3) | |
C1 | 0.75915 (17) | 0.70959 (17) | 0.23334 (16) | 0.0230 (4) | |
C2 | 0.62962 (17) | 0.73192 (16) | 0.25781 (16) | 0.0221 (4) | |
C3 | 0.56186 (18) | 0.68568 (17) | 0.35032 (17) | 0.0249 (4) | |
H3 | 0.6008 | 0.6255 | 0.4205 | 0.030* | |
C4 | 0.43510 (18) | 0.73193 (17) | 0.33472 (17) | 0.0253 (4) | |
C5 | 0.37556 (18) | 0.82104 (18) | 0.23277 (18) | 0.0280 (4) | |
H5 | 0.2884 | 0.8496 | 0.2260 | 0.034* | |
C6 | 0.44196 (18) | 0.86794 (18) | 0.14196 (17) | 0.0276 (4) | |
H6 | 0.4030 | 0.9292 | 0.0722 | 0.033* | |
C7 | 0.56748 (17) | 0.82128 (17) | 0.15782 (16) | 0.0236 (4) | |
C8 | 0.76507 (18) | 0.78429 (18) | 0.12401 (16) | 0.0243 (4) | |
C9 | 0.86352 (19) | 0.8079 (2) | 0.04658 (16) | 0.0293 (4) | |
C10 | 0.9528 (2) | 0.7157 (3) | 0.01943 (19) | 0.0390 (5) | |
H10 | 0.9541 | 0.6346 | 0.0539 | 0.047* | |
C11 | 1.0412 (2) | 0.7437 (3) | −0.0595 (2) | 0.0563 (8) | |
H11 | 1.1036 | 0.6819 | −0.0792 | 0.068* | |
C12 | 1.0364 (3) | 0.8610 (4) | −0.1074 (2) | 0.0602 (9) | |
C13 | 0.9495 (3) | 0.9538 (3) | −0.0828 (2) | 0.0540 (8) | |
H13 | 0.9490 | 1.0346 | −0.1184 | 0.065* | |
C14 | 0.8622 (2) | 0.9275 (2) | −0.00479 (18) | 0.0396 (5) | |
H14 | 0.8009 | 0.9905 | 0.0142 | 0.048* | |
C15 | 0.90404 (19) | 0.6917 (2) | 0.40407 (17) | 0.0312 (4) | |
H15 | 0.9739 | 0.6348 | 0.4598 | 0.037* | |
C16 | 0.7904 (2) | 0.7301 (2) | 0.47178 (19) | 0.0403 (5) | |
H16A | 0.8057 | 0.7705 | 0.5163 | 0.060* | |
H16B | 0.7725 | 0.6579 | 0.5229 | 0.060* | |
H16C | 0.7199 | 0.7865 | 0.4196 | 0.060* | |
C17 | 0.9410 (2) | 0.7973 (2) | 0.3244 (2) | 0.0382 (5) | |
H17A | 0.8714 | 0.8591 | 0.2732 | 0.057* | |
H17B | 1.0108 | 0.7679 | 0.2798 | 0.057* | |
H17C | 0.9648 | 0.8333 | 0.3687 | 0.057* | |
C18 | 0.43388 (17) | 0.21427 (17) | 0.14277 (16) | 0.0240 (4) | |
C19 | 0.46896 (18) | 0.29646 (17) | 0.04048 (16) | 0.0242 (4) | |
C20 | 0.57969 (18) | 0.30585 (19) | −0.00800 (17) | 0.0267 (4) | |
H20 | 0.6566 | 0.2501 | 0.0289 | 0.032* | |
C21 | 0.57303 (19) | 0.3995 (2) | −0.11194 (17) | 0.0292 (4) | |
C22 | 0.4612 (2) | 0.4823 (2) | −0.16880 (19) | 0.0336 (5) | |
H22 | 0.4609 | 0.5442 | −0.2410 | 0.040* | |
C23 | 0.3503 (2) | 0.4745 (2) | −0.12006 (18) | 0.0324 (4) | |
H23 | 0.2732 | 0.5295 | −0.1570 | 0.039* | |
C26 | 0.21380 (17) | 0.22260 (18) | 0.22001 (16) | 0.0249 (4) | |
C24 | 0.35885 (18) | 0.38246 (19) | −0.01535 (17) | 0.0266 (4) | |
C25 | 0.30780 (18) | 0.25643 (17) | 0.14309 (16) | 0.0245 (4) | |
C27 | 0.21988 (19) | 0.10232 (19) | 0.27135 (18) | 0.0292 (4) | |
H27 | 0.2879 | 0.0395 | 0.2582 | 0.035* | |
C28 | 0.1273 (2) | 0.0737 (2) | 0.34156 (18) | 0.0327 (4) | |
H28 | 0.1309 | −0.0082 | 0.3767 | 0.039* | |
C29 | 0.0304 (2) | 0.1664 (2) | 0.35910 (18) | 0.0334 (5) | |
C30 | 0.0208 (2) | 0.2862 (2) | 0.31029 (19) | 0.0343 (5) | |
H30 | −0.0474 | 0.3481 | 0.3246 | 0.041* | |
C31 | 0.11328 (19) | 0.31421 (19) | 0.23962 (18) | 0.0295 (4) | |
H31 | 0.1082 | 0.3965 | 0.2042 | 0.035* | |
C32 | 0.58508 (18) | 0.16381 (18) | 0.31956 (17) | 0.0265 (4) | |
H32 | 0.6135 | 0.2289 | 0.2633 | 0.032* | |
C33 | 0.6918 (2) | 0.0688 (2) | 0.40173 (19) | 0.0364 (5) | |
H33A | 0.7214 | 0.1084 | 0.4381 | 0.055* | |
H33B | 0.7588 | 0.0301 | 0.3601 | 0.055* | |
H33C | 0.6638 | 0.0069 | 0.4598 | 0.055* | |
C34 | 0.4752 (2) | 0.2221 (2) | 0.3806 (2) | 0.0370 (5) | |
H34A | 0.4504 | 0.1585 | 0.4399 | 0.055* | |
H34B | 0.4065 | 0.2778 | 0.3260 | 0.055* | |
H34C | 0.4978 | 0.2676 | 0.4151 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02965 (8) | 0.04227 (9) | 0.03667 (8) | −0.01834 (6) | 0.01302 (6) | −0.01549 (7) |
I2 | 0.03260 (8) | 0.04483 (9) | 0.03496 (8) | −0.02140 (7) | 0.00914 (6) | −0.01315 (7) |
S1 | 0.0195 (2) | 0.0205 (2) | 0.0256 (2) | −0.00292 (17) | 0.00131 (17) | −0.00429 (18) |
S2 | 0.0218 (2) | 0.0233 (2) | 0.0259 (2) | −0.00656 (18) | 0.00033 (18) | −0.00919 (18) |
F1 | 0.0640 (12) | 0.188 (3) | 0.0504 (10) | −0.0825 (15) | 0.0297 (9) | −0.0322 (13) |
F2 | 0.0415 (8) | 0.0622 (10) | 0.0547 (9) | −0.0280 (7) | 0.0253 (7) | −0.0214 (8) |
O1 | 0.0223 (7) | 0.0286 (7) | 0.0228 (6) | −0.0104 (6) | −0.0003 (5) | −0.0042 (6) |
O2 | 0.0287 (8) | 0.0248 (7) | 0.0361 (8) | −0.0061 (6) | 0.0028 (6) | 0.0004 (6) |
O3 | 0.0226 (7) | 0.0297 (8) | 0.0369 (8) | −0.0030 (6) | 0.0058 (6) | −0.0110 (6) |
O4 | 0.0222 (7) | 0.0291 (7) | 0.0266 (7) | −0.0082 (6) | 0.0005 (5) | −0.0074 (6) |
O5 | 0.0281 (8) | 0.0360 (8) | 0.0377 (8) | −0.0025 (6) | 0.0021 (6) | −0.0198 (7) |
O6 | 0.0323 (8) | 0.0290 (8) | 0.0377 (8) | −0.0141 (6) | −0.0035 (6) | −0.0051 (6) |
C1 | 0.0204 (9) | 0.0228 (9) | 0.0236 (9) | −0.0076 (7) | 0.0031 (7) | −0.0076 (7) |
C2 | 0.0194 (9) | 0.0206 (9) | 0.0257 (9) | −0.0057 (7) | 0.0009 (7) | −0.0098 (7) |
C3 | 0.0241 (9) | 0.0218 (9) | 0.0256 (9) | −0.0073 (7) | 0.0025 (7) | −0.0074 (7) |
C4 | 0.0235 (9) | 0.0237 (9) | 0.0311 (10) | −0.0103 (8) | 0.0070 (8) | −0.0130 (8) |
C5 | 0.0203 (9) | 0.0251 (9) | 0.0392 (11) | −0.0077 (8) | 0.0014 (8) | −0.0133 (9) |
C6 | 0.0228 (9) | 0.0242 (9) | 0.0308 (10) | −0.0066 (8) | −0.0038 (8) | −0.0057 (8) |
C7 | 0.0234 (9) | 0.0228 (9) | 0.0235 (9) | −0.0094 (7) | 0.0017 (7) | −0.0072 (7) |
C8 | 0.0225 (9) | 0.0260 (9) | 0.0246 (9) | −0.0088 (8) | 0.0002 (7) | −0.0098 (8) |
C9 | 0.0251 (10) | 0.0446 (12) | 0.0204 (9) | −0.0172 (9) | 0.0004 (7) | −0.0101 (9) |
C10 | 0.0270 (11) | 0.0594 (15) | 0.0297 (11) | −0.0122 (11) | 0.0021 (9) | −0.0196 (11) |
C11 | 0.0269 (12) | 0.107 (3) | 0.0342 (13) | −0.0167 (14) | 0.0046 (10) | −0.0342 (15) |
C12 | 0.0439 (15) | 0.118 (3) | 0.0278 (12) | −0.0539 (18) | 0.0096 (11) | −0.0165 (15) |
C13 | 0.0576 (17) | 0.084 (2) | 0.0306 (12) | −0.0534 (17) | 0.0019 (12) | −0.0057 (13) |
C14 | 0.0442 (13) | 0.0530 (14) | 0.0263 (10) | −0.0310 (12) | −0.0024 (9) | −0.0061 (10) |
C15 | 0.0256 (10) | 0.0328 (11) | 0.0277 (10) | −0.0045 (8) | −0.0064 (8) | −0.0077 (9) |
C16 | 0.0403 (13) | 0.0501 (14) | 0.0318 (11) | −0.0132 (11) | 0.0049 (10) | −0.0209 (11) |
C17 | 0.0351 (12) | 0.0357 (12) | 0.0466 (13) | −0.0147 (10) | 0.0017 (10) | −0.0168 (10) |
C18 | 0.0217 (9) | 0.0266 (9) | 0.0241 (9) | −0.0081 (8) | 0.0007 (7) | −0.0107 (8) |
C19 | 0.0257 (10) | 0.0256 (9) | 0.0222 (9) | −0.0090 (8) | −0.0003 (7) | −0.0097 (8) |
C20 | 0.0239 (10) | 0.0301 (10) | 0.0268 (9) | −0.0098 (8) | 0.0012 (8) | −0.0116 (8) |
C21 | 0.0291 (10) | 0.0344 (11) | 0.0280 (10) | −0.0155 (9) | 0.0049 (8) | −0.0130 (9) |
C22 | 0.0369 (12) | 0.0332 (11) | 0.0279 (10) | −0.0162 (9) | 0.0020 (9) | −0.0060 (9) |
C23 | 0.0299 (11) | 0.0317 (11) | 0.0303 (10) | −0.0092 (9) | −0.0027 (8) | −0.0072 (9) |
C26 | 0.0209 (9) | 0.0305 (10) | 0.0252 (9) | −0.0088 (8) | 0.0009 (7) | −0.0129 (8) |
C24 | 0.0241 (10) | 0.0310 (10) | 0.0265 (9) | −0.0125 (8) | 0.0030 (8) | −0.0110 (8) |
C25 | 0.0261 (10) | 0.0233 (9) | 0.0244 (9) | −0.0075 (8) | −0.0011 (7) | −0.0103 (8) |
C27 | 0.0233 (10) | 0.0288 (10) | 0.0364 (11) | −0.0084 (8) | 0.0025 (8) | −0.0147 (9) |
C28 | 0.0308 (11) | 0.0320 (11) | 0.0343 (11) | −0.0148 (9) | 0.0009 (9) | −0.0084 (9) |
C29 | 0.0275 (10) | 0.0467 (13) | 0.0303 (10) | −0.0199 (10) | 0.0089 (8) | −0.0151 (10) |
C30 | 0.0273 (11) | 0.0399 (12) | 0.0364 (11) | −0.0087 (9) | 0.0072 (9) | −0.0201 (10) |
C31 | 0.0268 (10) | 0.0286 (10) | 0.0339 (10) | −0.0090 (8) | 0.0027 (8) | −0.0144 (9) |
C32 | 0.0272 (10) | 0.0282 (10) | 0.0266 (9) | −0.0119 (8) | 0.0005 (8) | −0.0110 (8) |
C33 | 0.0315 (11) | 0.0394 (12) | 0.0364 (11) | −0.0100 (10) | −0.0066 (9) | −0.0129 (10) |
C34 | 0.0345 (12) | 0.0410 (12) | 0.0374 (12) | −0.0066 (10) | 0.0015 (9) | −0.0236 (10) |
I1—C4 | 2.0982 (19) | C15—C17 | 1.517 (3) |
I1—O2i | 3.3646 (15) | C15—C16 | 1.526 (3) |
I2—C21 | 2.098 (2) | C15—H15 | 1.0000 |
I2—O3ii | 3.2354 (14) | C16—H16A | 0.9800 |
S1—O2 | 1.4399 (15) | C16—H16B | 0.9800 |
S1—O3 | 1.4392 (14) | C16—H16C | 0.9800 |
S1—C1 | 1.7450 (19) | C17—H17A | 0.9800 |
S1—C15 | 1.787 (2) | C17—H17B | 0.9800 |
S2—O6 | 1.4331 (16) | C17—H17C | 0.9800 |
S2—O5 | 1.4400 (15) | C18—C25 | 1.371 (3) |
S2—C18 | 1.751 (2) | C18—C19 | 1.448 (3) |
S2—C32 | 1.791 (2) | C19—C24 | 1.389 (3) |
F1—C12 | 1.357 (3) | C19—C20 | 1.395 (3) |
F2—C29 | 1.354 (2) | C20—C21 | 1.383 (3) |
O1—C8 | 1.367 (2) | C20—H20 | 0.9500 |
O1—C7 | 1.377 (2) | C21—C22 | 1.399 (3) |
O4—C25 | 1.378 (2) | C22—C23 | 1.392 (3) |
O4—C24 | 1.379 (2) | C22—H22 | 0.9500 |
C1—C8 | 1.361 (3) | C23—C24 | 1.377 (3) |
C1—C2 | 1.454 (3) | C23—H23 | 0.9500 |
C2—C7 | 1.390 (3) | C26—C27 | 1.392 (3) |
C2—C3 | 1.398 (3) | C26—C31 | 1.395 (3) |
C3—C4 | 1.386 (3) | C26—C25 | 1.459 (3) |
C3—H3 | 0.9500 | C27—C28 | 1.385 (3) |
C4—C5 | 1.396 (3) | C27—H27 | 0.9500 |
C5—C6 | 1.377 (3) | C28—C29 | 1.373 (3) |
C5—H5 | 0.9500 | C28—H28 | 0.9500 |
C6—C7 | 1.372 (3) | C29—C30 | 1.373 (3) |
C6—H6 | 0.9500 | C30—C31 | 1.385 (3) |
C8—C9 | 1.467 (3) | C30—H30 | 0.9500 |
C9—C10 | 1.384 (3) | C31—H31 | 0.9500 |
C9—C14 | 1.402 (3) | C32—C34 | 1.522 (3) |
C10—C11 | 1.400 (3) | C32—C33 | 1.526 (3) |
C10—H10 | 0.9500 | C32—H32 | 1.0000 |
C11—C12 | 1.361 (5) | C33—H33A | 0.9800 |
C11—H11 | 0.9500 | C33—H33B | 0.9800 |
C12—C13 | 1.362 (5) | C33—H33C | 0.9800 |
C13—C14 | 1.379 (3) | C34—H34A | 0.9800 |
C13—H13 | 0.9500 | C34—H34B | 0.9800 |
C14—H14 | 0.9500 | C34—H34C | 0.9800 |
C4—I1—O2i | 152.77 (6) | H16A—C16—H16C | 109.5 |
C21—I2—O3ii | 170.66 (6) | H16B—C16—H16C | 109.5 |
O2—S1—O3 | 117.87 (9) | C15—C17—H17A | 109.5 |
O2—S1—C1 | 106.58 (9) | C15—C17—H17B | 109.5 |
O3—S1—C1 | 109.02 (9) | H17A—C17—H17B | 109.5 |
O2—S1—C15 | 108.55 (10) | C15—C17—H17C | 109.5 |
O3—S1—C15 | 107.76 (10) | H17A—C17—H17C | 109.5 |
C1—S1—C15 | 106.54 (9) | H17B—C17—H17C | 109.5 |
O6—S2—O5 | 118.36 (10) | C25—C18—C19 | 107.14 (17) |
O6—S2—C18 | 110.60 (9) | C25—C18—S2 | 129.91 (15) |
O5—S2—C18 | 106.18 (9) | C19—C18—S2 | 122.84 (14) |
O6—S2—C32 | 108.55 (9) | C24—C19—C20 | 119.06 (18) |
O5—S2—C32 | 108.78 (9) | C24—C19—C18 | 105.28 (17) |
C18—S2—C32 | 103.33 (9) | C20—C19—C18 | 135.65 (18) |
C8—O1—C7 | 107.10 (14) | C21—C20—C19 | 117.35 (19) |
C25—O4—C24 | 107.14 (15) | C21—C20—H20 | 121.3 |
C8—C1—C2 | 107.13 (17) | C19—C20—H20 | 121.3 |
C8—C1—S1 | 126.98 (15) | C20—C21—C22 | 122.63 (19) |
C2—C1—S1 | 125.85 (14) | C20—C21—I2 | 118.79 (15) |
C7—C2—C3 | 119.05 (17) | C22—C21—I2 | 118.57 (15) |
C7—C2—C1 | 104.66 (16) | C23—C22—C21 | 120.3 (2) |
C3—C2—C1 | 136.28 (18) | C23—C22—H22 | 119.9 |
C4—C3—C2 | 116.79 (18) | C21—C22—H22 | 119.9 |
C4—C3—H3 | 121.6 | C24—C23—C22 | 116.2 (2) |
C2—C3—H3 | 121.6 | C24—C23—H23 | 121.9 |
C3—C4—C5 | 122.73 (18) | C22—C23—H23 | 121.9 |
C3—C4—I1 | 119.58 (15) | C27—C26—C31 | 119.35 (18) |
C5—C4—I1 | 117.65 (14) | C27—C26—C25 | 121.84 (17) |
C6—C5—C4 | 120.62 (18) | C31—C26—C25 | 118.78 (18) |
C6—C5—H5 | 119.7 | C23—C24—O4 | 125.19 (18) |
C4—C5—H5 | 119.7 | C23—C24—C19 | 124.40 (19) |
C7—C6—C5 | 116.33 (18) | O4—C24—C19 | 110.35 (17) |
C7—C6—H6 | 121.8 | C18—C25—O4 | 110.08 (17) |
C5—C6—H6 | 121.8 | C18—C25—C26 | 136.33 (18) |
C6—C7—O1 | 125.00 (17) | O4—C25—C26 | 113.56 (16) |
C6—C7—C2 | 124.48 (18) | C28—C27—C26 | 120.40 (19) |
O1—C7—C2 | 110.49 (16) | C28—C27—H27 | 119.8 |
C1—C8—O1 | 110.61 (16) | C26—C27—H27 | 119.8 |
C1—C8—C9 | 135.85 (18) | C29—C28—C27 | 118.4 (2) |
O1—C8—C9 | 113.54 (16) | C29—C28—H28 | 120.8 |
C10—C9—C14 | 120.1 (2) | C27—C28—H28 | 120.8 |
C10—C9—C8 | 121.0 (2) | F2—C29—C30 | 118.2 (2) |
C14—C9—C8 | 118.8 (2) | F2—C29—C28 | 118.6 (2) |
C9—C10—C11 | 119.1 (3) | C30—C29—C28 | 123.15 (19) |
C9—C10—H10 | 120.5 | C29—C30—C31 | 118.14 (19) |
C11—C10—H10 | 120.5 | C29—C30—H30 | 120.9 |
C12—C11—C10 | 118.9 (3) | C31—C30—H30 | 120.9 |
C12—C11—H11 | 120.6 | C30—C31—C26 | 120.6 (2) |
C10—C11—H11 | 120.6 | C30—C31—H31 | 119.7 |
C11—C12—F1 | 117.2 (3) | C26—C31—H31 | 119.7 |
C11—C12—C13 | 123.5 (2) | C34—C32—C33 | 111.88 (17) |
F1—C12—C13 | 119.3 (3) | C34—C32—S2 | 110.03 (15) |
C12—C13—C14 | 118.3 (3) | C33—C32—S2 | 108.70 (14) |
C12—C13—H13 | 120.8 | C34—C32—H32 | 108.7 |
C14—C13—H13 | 120.8 | C33—C32—H32 | 108.7 |
C13—C14—C9 | 120.2 (3) | S2—C32—H32 | 108.7 |
C13—C14—H14 | 119.9 | C32—C33—H33A | 109.5 |
C9—C14—H14 | 119.9 | C32—C33—H33B | 109.5 |
C17—C15—C16 | 113.35 (19) | H33A—C33—H33B | 109.5 |
C17—C15—S1 | 110.96 (15) | C32—C33—H33C | 109.5 |
C16—C15—S1 | 110.46 (16) | H33A—C33—H33C | 109.5 |
C17—C15—H15 | 107.3 | H33B—C33—H33C | 109.5 |
C16—C15—H15 | 107.3 | C32—C34—H34A | 109.5 |
S1—C15—H15 | 107.3 | C32—C34—H34B | 109.5 |
C15—C16—H16A | 109.5 | H34A—C34—H34B | 109.5 |
C15—C16—H16B | 109.5 | C32—C34—H34C | 109.5 |
H16A—C16—H16B | 109.5 | H34A—C34—H34C | 109.5 |
C15—C16—H16C | 109.5 | H34B—C34—H34C | 109.5 |
O2—S1—C1—C8 | −152.76 (18) | O6—S2—C18—C25 | 17.2 (2) |
O3—S1—C1—C8 | −24.6 (2) | O5—S2—C18—C25 | 146.80 (18) |
C15—S1—C1—C8 | 91.48 (19) | C32—S2—C18—C25 | −98.80 (19) |
O2—S1—C1—C2 | 29.66 (19) | O6—S2—C18—C19 | −167.17 (15) |
O3—S1—C1—C2 | 157.87 (16) | O5—S2—C18—C19 | −37.57 (18) |
C15—S1—C1—C2 | −86.10 (18) | C32—S2—C18—C19 | 76.83 (17) |
C8—C1—C2—C7 | −0.2 (2) | C25—C18—C19—C24 | −1.1 (2) |
S1—C1—C2—C7 | 177.74 (14) | S2—C18—C19—C24 | −177.63 (14) |
C8—C1—C2—C3 | 178.5 (2) | C25—C18—C19—C20 | 178.6 (2) |
S1—C1—C2—C3 | −3.6 (3) | S2—C18—C19—C20 | 2.1 (3) |
C7—C2—C3—C4 | 1.0 (3) | C24—C19—C20—C21 | −1.9 (3) |
C1—C2—C3—C4 | −177.6 (2) | C18—C19—C20—C21 | 178.4 (2) |
C2—C3—C4—C5 | −0.5 (3) | C19—C20—C21—C22 | −0.5 (3) |
C2—C3—C4—I1 | 177.18 (13) | C19—C20—C21—I2 | −179.34 (14) |
O2i—I1—C4—C3 | −102.08 (18) | O3ii—I2—C21—C20 | −30.8 (5) |
O2i—I1—C4—C5 | 75.7 (2) | O3ii—I2—C21—C22 | 150.3 (3) |
C3—C4—C5—C6 | −0.4 (3) | C20—C21—C22—C23 | 1.5 (3) |
I1—C4—C5—C6 | −178.08 (15) | I2—C21—C22—C23 | −179.71 (16) |
C4—C5—C6—C7 | 0.7 (3) | C21—C22—C23—C24 | 0.1 (3) |
C5—C6—C7—O1 | 177.68 (18) | C22—C23—C24—O4 | −179.66 (19) |
C5—C6—C7—C2 | −0.1 (3) | C22—C23—C24—C19 | −2.7 (3) |
C8—O1—C7—C6 | −178.10 (19) | C25—O4—C24—C23 | 177.04 (19) |
C8—O1—C7—C2 | 0.0 (2) | C25—O4—C24—C19 | −0.2 (2) |
C3—C2—C7—C6 | −0.7 (3) | C20—C19—C24—C23 | 3.7 (3) |
C1—C2—C7—C6 | 178.25 (18) | C18—C19—C24—C23 | −176.46 (19) |
C3—C2—C7—O1 | −178.81 (16) | C20—C19—C24—O4 | −178.95 (16) |
C1—C2—C7—O1 | 0.2 (2) | C18—C19—C24—O4 | 0.8 (2) |
C2—C1—C8—O1 | 0.2 (2) | C19—C18—C25—O4 | 1.0 (2) |
S1—C1—C8—O1 | −177.71 (14) | S2—C18—C25—O4 | 177.20 (14) |
C2—C1—C8—C9 | −179.6 (2) | C19—C18—C25—C26 | −176.7 (2) |
S1—C1—C8—C9 | 2.4 (3) | S2—C18—C25—C26 | −0.5 (3) |
C7—O1—C8—C1 | −0.1 (2) | C24—O4—C25—C18 | −0.5 (2) |
C7—O1—C8—C9 | 179.75 (16) | C24—O4—C25—C26 | 177.77 (15) |
C1—C8—C9—C10 | 59.0 (3) | C27—C26—C25—C18 | −46.5 (3) |
O1—C8—C9—C10 | −120.9 (2) | C31—C26—C25—C18 | 135.5 (2) |
C1—C8—C9—C14 | −124.5 (3) | C27—C26—C25—O4 | 135.87 (19) |
O1—C8—C9—C14 | 55.7 (2) | C31—C26—C25—O4 | −42.1 (2) |
C14—C9—C10—C11 | 0.1 (3) | C31—C26—C27—C28 | −0.2 (3) |
C8—C9—C10—C11 | 176.64 (19) | C25—C26—C27—C28 | −178.22 (19) |
C9—C10—C11—C12 | −0.2 (3) | C26—C27—C28—C29 | −0.1 (3) |
C10—C11—C12—F1 | −179.8 (2) | C27—C28—C29—F2 | −179.78 (19) |
C10—C11—C12—C13 | 0.0 (4) | C27—C28—C29—C30 | 0.1 (3) |
C11—C12—C13—C14 | 0.3 (4) | F2—C29—C30—C31 | −179.8 (2) |
F1—C12—C13—C14 | −179.9 (2) | C28—C29—C30—C31 | 0.3 (3) |
C12—C13—C14—C9 | −0.4 (4) | C29—C30—C31—C26 | −0.7 (3) |
C10—C9—C14—C13 | 0.2 (3) | C27—C26—C31—C30 | 0.7 (3) |
C8—C9—C14—C13 | −176.4 (2) | C25—C26—C31—C30 | 178.72 (19) |
O2—S1—C15—C17 | −178.23 (14) | O6—S2—C32—C34 | −52.80 (17) |
O3—S1—C15—C17 | 53.08 (17) | O5—S2—C32—C34 | 177.16 (15) |
C1—S1—C15—C17 | −63.79 (17) | C18—S2—C32—C34 | 64.64 (16) |
O2—S1—C15—C16 | −51.66 (17) | O6—S2—C32—C33 | 70.04 (16) |
O3—S1—C15—C16 | 179.65 (15) | O5—S2—C32—C33 | −60.00 (17) |
C1—S1—C15—C16 | 62.77 (17) | C18—S2—C32—C33 | −172.52 (15) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1iii | 0.95 | 2.56 | 3.418 (2) | 150 |
C15—H15···O2iv | 1.00 | 2.52 | 3.520 (3) | 177 |
C30—H30···O2v | 0.95 | 2.58 | 3.463 (3) | 155 |
C31—H31···O3v | 0.95 | 2.58 | 3.260 (2) | 129 |
Symmetry codes: (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H14FIO3S |
Mr | 444.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 11.7419 (2), 12.8226 (2), 12.8474 (2) |
α, β, γ (°) | 66.576 (1), 82.703 (1), 67.769 (1) |
V (Å3) | 1642.36 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.10 |
Crystal size (mm) | 0.31 × 0.22 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.594, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30779, 8149, 7224 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.060, 1.01 |
No. of reflections | 8149 |
No. of parameters | 419 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.65, −0.88 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.95 | 2.56 | 3.418 (2) | 150.1 |
C15—H15···O2ii | 1.00 | 2.52 | 3.520 (3) | 176.9 |
C30—H30···O2iii | 0.95 | 2.58 | 3.463 (3) | 155.4 |
C31—H31···O3iii | 0.95 | 2.58 | 3.260 (2) | 129.2 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z. |
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. (2010a). Acta Cryst. E66, o1043. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o3261. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS 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 ongoing study of 2-(4-fluorophenyl)-5-iodo-1-benzofuran derivatives containing ethylsulfinyl (Choi et al., 2010a) and isopropylsulfinyl (Choi et al., 2010b) substituents in 3-position, we report herein the crystal structure of the title compound which crystallizes with two symmetrically independent molecules, A and B, in the asymmetric unit.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.013 (2)and 0.016 (2) Å, for A and B, respectively, from the least-squares plane defined by its nine constituent atoms. The dihedral angles between the 4-fluorophenyl ring and the mean plane of the benzofuran fragment are 57.71 (7)° in molecule A and 44.95 (7)° in molecule B, respectively. In the crystal packing (Fig. 2), molecules are linked by weak C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also features I···O halogen-bondings between the iodine and the oxygen of the O═S═O unit [I1···O2iv = 3.3646 (15) Å , C4—I1···O2iv = 152.77 (6)° & I2···O3v = 3.2354 (14) Å, C21—I2···O3v = 170.66 (6)°] (Politzer et al., 2007).