organic compounds
Ethyl 2-(5-cyclohexyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate
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
In the title compound, C19H24O4S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations with site-occupancy factors of 0.875 (4) and 0.125 (4).
Related literature
For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl) acetate derivatives, see: Choi et al. (2007a,b; 2009).
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/S1600536811024925/bv2187sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811024925/bv2187Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811024925/bv2187Isup3.cml
77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of ethyl 2-(5-cyclohexyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (298 mg, 0.9 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
(hexane–ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 360–361 K; Rf = 0.41 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.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, methylene, and 1.5Ueq(C) for methyl H atoms. The O atom of sulfinyl group is disordered over two positions with site-ccupancy factors, from
of 0.875 (4) (part A) and 0.125 (4) (part B). The S—O distances were restrained to 0.001 Å using command SADI and DELU.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).C19H24O4S | F(000) = 744 |
Mr = 348.45 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3275 reflections |
a = 16.1065 (7) Å | θ = 2.2–26.5° |
b = 4.8485 (2) Å | µ = 0.21 mm−1 |
c = 22.3653 (11) Å | T = 173 K |
β = 91.010 (2)° | Block, colourless |
V = 1746.29 (14) Å3 | 0.28 × 0.20 × 0.18 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 3804 independent reflections |
Radiation source: rotating anode | 2917 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.049 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 1.3° |
ϕ and ω scans | h = −20→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −6→6 |
Tmin = 0.945, Tmax = 0.964 | l = −28→28 |
15388 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)] = 0.052 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0537P)2 + 1.3587P] where P = (Fo2 + 2Fc2)/3 |
3804 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.56 e Å−3 |
67 restraints | Δρmin = −0.38 e Å−3 |
C19H24O4S | V = 1746.29 (14) Å3 |
Mr = 348.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.1065 (7) Å | µ = 0.21 mm−1 |
b = 4.8485 (2) Å | T = 173 K |
c = 22.3653 (11) Å | 0.28 × 0.20 × 0.18 mm |
β = 91.010 (2)° |
Bruker SMART APEXII CCD diffractometer | 3804 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2917 reflections with I > 2σ(I) |
Tmin = 0.945, Tmax = 0.964 | Rint = 0.049 |
15388 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 67 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.56 e Å−3 |
3804 reflections | Δρmin = −0.38 e Å−3 |
229 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 | Occ. (<1) | |
S1 | 0.36614 (3) | 0.95799 (12) | 0.29116 (3) | 0.03096 (17) | |
O1 | 0.18470 (9) | 0.6531 (3) | 0.38601 (6) | 0.0325 (4) | |
O2 | 0.38323 (12) | 0.5969 (4) | 0.44371 (8) | 0.0532 (5) | |
O3 | 0.36351 (11) | 0.9044 (4) | 0.51602 (7) | 0.0443 (5) | |
O4A | 0.35467 (11) | 1.0448 (4) | 0.22886 (8) | 0.0392 (6) | 0.875 (4) |
O4B | 0.3933 (9) | 1.160 (2) | 0.3361 (5) | 0.057 (4) | 0.125 (4) |
C1 | 0.27598 (12) | 0.7963 (4) | 0.31809 (9) | 0.0266 (5) | |
C2 | 0.22021 (12) | 0.6069 (4) | 0.28840 (9) | 0.0253 (4) | |
C3 | 0.21169 (12) | 0.5003 (4) | 0.23082 (9) | 0.0262 (5) | |
H3 | 0.2479 | 0.5575 | 0.2001 | 0.031* | |
C4 | 0.14931 (12) | 0.3085 (4) | 0.21906 (9) | 0.0257 (5) | |
C5 | 0.09692 (13) | 0.2284 (5) | 0.26516 (10) | 0.0316 (5) | |
H5 | 0.0548 | 0.0962 | 0.2567 | 0.038* | |
C6 | 0.10392 (13) | 0.3335 (5) | 0.32258 (10) | 0.0327 (5) | |
H6 | 0.0679 | 0.2773 | 0.3535 | 0.039* | |
C7 | 0.16600 (13) | 0.5242 (5) | 0.33243 (9) | 0.0283 (5) | |
C8 | 0.25217 (13) | 0.8178 (5) | 0.37491 (10) | 0.0297 (5) | |
C9 | 0.13521 (13) | 0.1884 (4) | 0.15724 (9) | 0.0269 (5) | |
H9 | 0.1225 | −0.0119 | 0.1624 | 0.032* | |
C10 | 0.05931 (13) | 0.3205 (5) | 0.12640 (9) | 0.0308 (5) | |
H10A | 0.0100 | 0.2924 | 0.1515 | 0.037* | |
H10B | 0.0686 | 0.5216 | 0.1227 | 0.037* | |
C11 | 0.04212 (14) | 0.1998 (6) | 0.06457 (10) | 0.0379 (6) | |
H11A | 0.0255 | 0.0042 | 0.0686 | 0.045* | |
H11B | −0.0046 | 0.3007 | 0.0453 | 0.045* | |
C12 | 0.11783 (14) | 0.2186 (5) | 0.02536 (10) | 0.0362 (5) | |
H12A | 0.1304 | 0.4148 | 0.0173 | 0.043* | |
H12B | 0.1058 | 0.1270 | −0.0134 | 0.043* | |
C13 | 0.19283 (15) | 0.0828 (5) | 0.05528 (10) | 0.0358 (5) | |
H13A | 0.2420 | 0.1071 | 0.0299 | 0.043* | |
H13B | 0.1825 | −0.1175 | 0.0595 | 0.043* | |
C14 | 0.21039 (13) | 0.2080 (5) | 0.11680 (9) | 0.0317 (5) | |
H14A | 0.2261 | 0.4041 | 0.1121 | 0.038* | |
H14B | 0.2579 | 0.1106 | 0.1359 | 0.038* | |
C15 | 0.28665 (14) | 0.9685 (5) | 0.42765 (10) | 0.0338 (5) | |
H15A | 0.2408 | 1.0187 | 0.4544 | 0.041* | |
H15B | 0.3131 | 1.1413 | 0.4141 | 0.041* | |
C16 | 0.34984 (14) | 0.7987 (5) | 0.46210 (10) | 0.0347 (5) | |
C17 | 0.42421 (19) | 0.7598 (7) | 0.55380 (13) | 0.0591 (8) | |
H17A | 0.4054 | 0.5687 | 0.5612 | 0.071* | |
H17B | 0.4784 | 0.7519 | 0.5337 | 0.071* | |
C18 | 0.4327 (2) | 0.9083 (9) | 0.61010 (14) | 0.0775 (11) | |
H18A | 0.4544 | 1.0937 | 0.6026 | 0.116* | |
H18B | 0.4711 | 0.8088 | 0.6369 | 0.116* | |
H18C | 0.3783 | 0.9225 | 0.6288 | 0.116* | |
C19 | 0.42883 (14) | 0.6559 (5) | 0.28894 (12) | 0.0403 (6) | |
H19A | 0.4039 | 0.5228 | 0.2610 | 0.060* | |
H19B | 0.4325 | 0.5739 | 0.3290 | 0.060* | |
H19C | 0.4846 | 0.7046 | 0.2757 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0292 (3) | 0.0237 (3) | 0.0402 (3) | −0.0018 (2) | 0.0030 (2) | 0.0002 (3) |
O1 | 0.0286 (8) | 0.0414 (9) | 0.0276 (8) | −0.0026 (7) | 0.0032 (6) | −0.0066 (7) |
O2 | 0.0576 (12) | 0.0484 (11) | 0.0531 (11) | 0.0198 (10) | −0.0138 (9) | −0.0149 (10) |
O3 | 0.0490 (10) | 0.0465 (11) | 0.0368 (9) | 0.0081 (9) | −0.0149 (8) | −0.0089 (8) |
O4A | 0.0363 (10) | 0.0412 (12) | 0.0402 (11) | −0.0020 (9) | 0.0010 (8) | 0.0072 (9) |
O4B | 0.058 (9) | 0.030 (7) | 0.083 (9) | −0.013 (6) | −0.001 (8) | −0.008 (7) |
C1 | 0.0227 (10) | 0.0267 (11) | 0.0302 (10) | 0.0026 (9) | −0.0007 (8) | −0.0023 (9) |
C2 | 0.0211 (9) | 0.0254 (11) | 0.0294 (10) | 0.0025 (9) | 0.0000 (8) | −0.0003 (9) |
C3 | 0.0242 (10) | 0.0272 (11) | 0.0271 (10) | 0.0014 (9) | −0.0001 (8) | −0.0002 (9) |
C4 | 0.0251 (10) | 0.0253 (11) | 0.0266 (10) | 0.0027 (9) | −0.0009 (8) | −0.0011 (9) |
C5 | 0.0279 (11) | 0.0319 (12) | 0.0350 (11) | −0.0035 (10) | −0.0028 (9) | −0.0014 (10) |
C6 | 0.0267 (10) | 0.0405 (13) | 0.0312 (11) | −0.0049 (10) | 0.0050 (9) | −0.0006 (11) |
C7 | 0.0251 (10) | 0.0318 (12) | 0.0279 (10) | 0.0028 (9) | −0.0016 (8) | −0.0043 (10) |
C8 | 0.0245 (10) | 0.0308 (12) | 0.0336 (11) | −0.0002 (9) | 0.0002 (9) | −0.0048 (10) |
C9 | 0.0313 (11) | 0.0222 (11) | 0.0270 (10) | −0.0006 (9) | −0.0023 (8) | −0.0014 (9) |
C10 | 0.0248 (10) | 0.0342 (12) | 0.0335 (11) | −0.0021 (10) | −0.0017 (9) | −0.0003 (10) |
C11 | 0.0323 (12) | 0.0469 (15) | 0.0341 (12) | −0.0067 (11) | −0.0080 (9) | 0.0010 (11) |
C12 | 0.0384 (12) | 0.0431 (14) | 0.0270 (11) | −0.0051 (11) | −0.0041 (9) | −0.0024 (11) |
C13 | 0.0416 (13) | 0.0358 (13) | 0.0301 (11) | 0.0010 (11) | 0.0030 (10) | −0.0049 (11) |
C14 | 0.0297 (11) | 0.0350 (12) | 0.0305 (11) | 0.0053 (10) | −0.0016 (9) | −0.0043 (10) |
C15 | 0.0338 (11) | 0.0365 (13) | 0.0309 (11) | 0.0016 (10) | −0.0017 (9) | −0.0073 (10) |
C16 | 0.0322 (12) | 0.0371 (13) | 0.0346 (12) | −0.0027 (11) | −0.0018 (9) | −0.0044 (11) |
C17 | 0.0637 (18) | 0.0570 (18) | 0.0557 (17) | 0.0124 (16) | −0.0278 (15) | −0.0027 (15) |
C18 | 0.077 (2) | 0.102 (3) | 0.0525 (18) | 0.025 (2) | −0.0274 (16) | −0.0068 (19) |
C19 | 0.0274 (11) | 0.0317 (13) | 0.0620 (16) | 0.0040 (10) | 0.0077 (11) | 0.0001 (12) |
S1—O4B | 1.463 (2) | C10—H10A | 0.9900 |
S1—O4A | 1.4641 (19) | C10—H10B | 0.9900 |
S1—C1 | 1.765 (2) | C11—C12 | 1.517 (3) |
S1—C19 | 1.780 (2) | C11—H11A | 0.9900 |
O1—C8 | 1.375 (3) | C11—H11B | 0.9900 |
O1—C7 | 1.380 (2) | C12—C13 | 1.520 (3) |
O2—C16 | 1.193 (3) | C12—H12A | 0.9900 |
O3—C16 | 1.325 (3) | C12—H12B | 0.9900 |
O3—C17 | 1.460 (3) | C13—C14 | 1.526 (3) |
C1—C8 | 1.338 (3) | C13—H13A | 0.9900 |
C1—C2 | 1.439 (3) | C13—H13B | 0.9900 |
C2—C7 | 1.387 (3) | C14—H14A | 0.9900 |
C2—C3 | 1.392 (3) | C14—H14B | 0.9900 |
C3—C4 | 1.391 (3) | C15—C16 | 1.510 (3) |
C3—H3 | 0.9500 | C15—H15A | 0.9900 |
C4—C5 | 1.399 (3) | C15—H15B | 0.9900 |
C4—C9 | 1.514 (3) | C17—C18 | 1.455 (4) |
C5—C6 | 1.385 (3) | C17—H17A | 0.9900 |
C5—H5 | 0.9500 | C17—H17B | 0.9900 |
C6—C7 | 1.377 (3) | C18—H18A | 0.9800 |
C6—H6 | 0.9500 | C18—H18B | 0.9800 |
C8—C15 | 1.487 (3) | C18—H18C | 0.9800 |
C9—C14 | 1.527 (3) | C19—H19A | 0.9800 |
C9—C10 | 1.533 (3) | C19—H19B | 0.9800 |
C9—H9 | 1.0000 | C19—H19C | 0.9800 |
C10—C11 | 1.523 (3) | ||
O4B—S1—O4A | 119.5 (6) | C10—C11—H11B | 109.3 |
O4B—S1—C1 | 107.5 (6) | H11A—C11—H11B | 108.0 |
O4A—S1—C1 | 111.19 (10) | C11—C12—C13 | 111.10 (19) |
O4B—S1—C19 | 114.0 (6) | C11—C12—H12A | 109.4 |
O4A—S1—C19 | 105.79 (12) | C13—C12—H12A | 109.4 |
C1—S1—C19 | 96.58 (11) | C11—C12—H12B | 109.4 |
C8—O1—C7 | 105.52 (16) | C13—C12—H12B | 109.4 |
C16—O3—C17 | 116.1 (2) | H12A—C12—H12B | 108.0 |
C8—C1—C2 | 107.52 (19) | C12—C13—C14 | 110.96 (19) |
C8—C1—S1 | 122.73 (17) | C12—C13—H13A | 109.4 |
C2—C1—S1 | 129.54 (16) | C14—C13—H13A | 109.4 |
C7—C2—C3 | 119.77 (19) | C12—C13—H13B | 109.4 |
C7—C2—C1 | 104.63 (18) | C14—C13—H13B | 109.4 |
C3—C2—C1 | 135.6 (2) | H13A—C13—H13B | 108.0 |
C4—C3—C2 | 118.8 (2) | C13—C14—C9 | 111.91 (18) |
C4—C3—H3 | 120.6 | C13—C14—H14A | 109.2 |
C2—C3—H3 | 120.6 | C9—C14—H14A | 109.2 |
C3—C4—C5 | 119.3 (2) | C13—C14—H14B | 109.2 |
C3—C4—C9 | 121.74 (19) | C9—C14—H14B | 109.2 |
C5—C4—C9 | 118.92 (19) | H14A—C14—H14B | 107.9 |
C6—C5—C4 | 122.8 (2) | C8—C15—C16 | 112.1 (2) |
C6—C5—H5 | 118.6 | C8—C15—H15A | 109.2 |
C4—C5—H5 | 118.6 | C16—C15—H15A | 109.2 |
C7—C6—C5 | 116.3 (2) | C8—C15—H15B | 109.2 |
C7—C6—H6 | 121.9 | C16—C15—H15B | 109.2 |
C5—C6—H6 | 121.9 | H15A—C15—H15B | 107.9 |
C6—C7—O1 | 126.1 (2) | O2—C16—O3 | 124.2 (2) |
C6—C7—C2 | 123.0 (2) | O2—C16—C15 | 125.1 (2) |
O1—C7—C2 | 110.79 (18) | O3—C16—C15 | 110.7 (2) |
C1—C8—O1 | 111.53 (18) | C18—C17—O3 | 108.3 (2) |
C1—C8—C15 | 133.0 (2) | C18—C17—H17A | 110.0 |
O1—C8—C15 | 115.31 (19) | O3—C17—H17A | 110.0 |
C4—C9—C14 | 114.16 (17) | C18—C17—H17B | 110.0 |
C4—C9—C10 | 110.85 (17) | O3—C17—H17B | 110.0 |
C14—C9—C10 | 110.00 (18) | H17A—C17—H17B | 108.4 |
C4—C9—H9 | 107.2 | C17—C18—H18A | 109.5 |
C14—C9—H9 | 107.2 | C17—C18—H18B | 109.5 |
C10—C9—H9 | 107.2 | H18A—C18—H18B | 109.5 |
C11—C10—C9 | 112.27 (19) | C17—C18—H18C | 109.5 |
C11—C10—H10A | 109.2 | H18A—C18—H18C | 109.5 |
C9—C10—H10A | 109.2 | H18B—C18—H18C | 109.5 |
C11—C10—H10B | 109.2 | S1—C19—H19A | 109.5 |
C9—C10—H10B | 109.2 | S1—C19—H19B | 109.5 |
H10A—C10—H10B | 107.9 | H19A—C19—H19B | 109.5 |
C12—C11—C10 | 111.51 (18) | S1—C19—H19C | 109.5 |
C12—C11—H11A | 109.3 | H19A—C19—H19C | 109.5 |
C10—C11—H11A | 109.3 | H19B—C19—H19C | 109.5 |
C12—C11—H11B | 109.3 | ||
O4B—S1—C1—C8 | −13.8 (7) | C2—C1—C8—O1 | 0.8 (2) |
O4A—S1—C1—C8 | −146.31 (19) | S1—C1—C8—O1 | −174.34 (14) |
C19—S1—C1—C8 | 103.9 (2) | C2—C1—C8—C15 | 176.7 (2) |
O4B—S1—C1—C2 | 172.3 (7) | S1—C1—C8—C15 | 1.6 (4) |
O4A—S1—C1—C2 | 39.7 (2) | C7—O1—C8—C1 | −0.3 (2) |
C19—S1—C1—C2 | −70.1 (2) | C7—O1—C8—C15 | −176.97 (19) |
C8—C1—C2—C7 | −0.9 (2) | C3—C4—C9—C14 | 21.3 (3) |
S1—C1—C2—C7 | 173.75 (17) | C5—C4—C9—C14 | −160.1 (2) |
C8—C1—C2—C3 | 179.9 (2) | C3—C4—C9—C10 | −103.6 (2) |
S1—C1—C2—C3 | −5.4 (4) | C5—C4—C9—C10 | 75.0 (2) |
C7—C2—C3—C4 | −1.0 (3) | C4—C9—C10—C11 | −178.72 (18) |
C1—C2—C3—C4 | 178.1 (2) | C14—C9—C10—C11 | 54.1 (2) |
C2—C3—C4—C5 | 0.1 (3) | C9—C10—C11—C12 | −54.8 (3) |
C2—C3—C4—C9 | 178.68 (19) | C10—C11—C12—C13 | 55.2 (3) |
C3—C4—C5—C6 | 0.5 (3) | C11—C12—C13—C14 | −55.9 (3) |
C9—C4—C5—C6 | −178.2 (2) | C12—C13—C14—C9 | 56.5 (3) |
C4—C5—C6—C7 | 0.0 (3) | C4—C9—C14—C13 | 179.72 (18) |
C5—C6—C7—O1 | −179.3 (2) | C10—C9—C14—C13 | −54.9 (2) |
C5—C6—C7—C2 | −1.0 (3) | C1—C8—C15—C16 | −88.6 (3) |
C8—O1—C7—C6 | 178.2 (2) | O1—C8—C15—C16 | 87.2 (2) |
C8—O1—C7—C2 | −0.3 (2) | C17—O3—C16—O2 | 0.5 (4) |
C3—C2—C7—C6 | 1.5 (3) | C17—O3—C16—C15 | −179.5 (2) |
C1—C2—C7—C6 | −177.8 (2) | C8—C15—C16—O2 | 16.1 (3) |
C3—C2—C7—O1 | −179.89 (18) | C8—C15—C16—O3 | −163.9 (2) |
C1—C2—C7—O1 | 0.8 (2) | C16—O3—C17—C18 | 178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14B···O4Ai | 0.99 | 2.60 | 3.479 (3) | 149 |
C15—H15B···O2ii | 0.99 | 2.56 | 3.437 (3) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C19H24O4S |
Mr | 348.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 16.1065 (7), 4.8485 (2), 22.3653 (11) |
β (°) | 91.010 (2) |
V (Å3) | 1746.29 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.28 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.945, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15388, 3804, 2917 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.132, 1.02 |
No. of reflections | 3804 |
No. of parameters | 229 |
No. of restraints | 67 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.38 |
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 |
C14—H14B···O4Ai | 0.99 | 2.60 | 3.479 (3) | 149 |
C15—H15B···O2ii | 0.99 | 2.56 | 3.437 (3) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
References
Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
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. (2007a). Acta Cryst. E63, o3839. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o3850. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o1826. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. 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
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS 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.
Recently, many compounds containing a benzofuran moiety have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al. , 2009, Galal et al. , 2009, Khan et al. , 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al. , 2003). As a part of our ongoing study of the substituent effect on the solid state structures of ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues (Choi et al., 2007a,b; 2009), we report herein on the crystal structure of the title compound
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.875 (3) (part A) and 0.125 (4) (part B). The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfinyl group (Table 1; C14—H14B···O4Ai), and the second one between an H atom of the benzylic methylene group and the O atom of the carbonyl group (Table 1; C15—H15B···O2ii).