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

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ISSN: 2056-9890

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

(Received 1 June 2011; accepted 24 June 2011; online 2 July 2011)

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[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For structural studies of related ethyl 2-(3-methyl­sulfinyl-1-benzofuran-2-yl) acetate derivatives, see: Choi et al. (2007a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3839.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o3850.]; 2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o1826.]).

[Scheme 1]

Experimental

Crystal data
  • C19H24O4S

  • Mr = 348.45

  • Monoclinic, P 21 /c

  • a = 16.1065 (7) Å

  • b = 4.8485 (2) Å

  • c = 22.3653 (11) Å

  • β = 91.010 (2)°

  • V = 1746.29 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 173 K

  • 0.28 × 0.20 × 0.18 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 = 0.945, Tmax = 0.964

  • 15388 measured reflections

  • 3804 independent reflections

  • 2917 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.132

  • S = 1.02

  • 3804 reflections

  • 229 parameters

  • 67 restraints

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.

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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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

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).

Related literature top

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 top

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 column chromatography (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.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methine, 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 refinement 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.

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 (Farrugia, 1997) 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 a small spheres of arbitrary radius. 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).
[Figure 2] Fig. 2. A view of the C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x, y - 1, z; (ii) x, y + 1, z.]
Ethyl 2-(5-cyclohexyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate top
Crystal data top
C19H24O4SF(000) = 744
Mr = 348.45Dx = 1.325 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3275 reflections
a = 16.1065 (7) Åθ = 2.2–26.5°
b = 4.8485 (2) ŵ = 0.21 mm1
c = 22.3653 (11) ÅT = 173 K
β = 91.010 (2)°Block, colourless
V = 1746.29 (14) Å30.28 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
3804 independent reflections
Radiation source: rotating anode2917 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.049
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.3°
ϕ and ω scansh = 2019
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 66
Tmin = 0.945, Tmax = 0.964l = 2828
15388 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)] = 0.052Hydrogen site location: difference Fourier map
wR(F2) = 0.132H-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 parametersΔρmax = 0.56 e Å3
67 restraintsΔρmin = 0.38 e Å3
Crystal data top
C19H24O4SV = 1746.29 (14) Å3
Mr = 348.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.1065 (7) ŵ = 0.21 mm1
b = 4.8485 (2) ÅT = 173 K
c = 22.3653 (11) Å0.28 × 0.20 × 0.18 mm
β = 91.010 (2)°
Data collection top
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 = 0.964Rint = 0.049
15388 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05267 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.02Δρmax = 0.56 e Å3
3804 reflectionsΔρmin = 0.38 e Å3
229 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*/UeqOcc. (<1)
S10.36614 (3)0.95799 (12)0.29116 (3)0.03096 (17)
O10.18470 (9)0.6531 (3)0.38601 (6)0.0325 (4)
O20.38323 (12)0.5969 (4)0.44371 (8)0.0532 (5)
O30.36351 (11)0.9044 (4)0.51602 (7)0.0443 (5)
O4A0.35467 (11)1.0448 (4)0.22886 (8)0.0392 (6)0.875 (4)
O4B0.3933 (9)1.160 (2)0.3361 (5)0.057 (4)0.125 (4)
C10.27598 (12)0.7963 (4)0.31809 (9)0.0266 (5)
C20.22021 (12)0.6069 (4)0.28840 (9)0.0253 (4)
C30.21169 (12)0.5003 (4)0.23082 (9)0.0262 (5)
H30.24790.55750.20010.031*
C40.14931 (12)0.3085 (4)0.21906 (9)0.0257 (5)
C50.09692 (13)0.2284 (5)0.26516 (10)0.0316 (5)
H50.05480.09620.25670.038*
C60.10392 (13)0.3335 (5)0.32258 (10)0.0327 (5)
H60.06790.27730.35350.039*
C70.16600 (13)0.5242 (5)0.33243 (9)0.0283 (5)
C80.25217 (13)0.8178 (5)0.37491 (10)0.0297 (5)
C90.13521 (13)0.1884 (4)0.15724 (9)0.0269 (5)
H90.12250.01190.16240.032*
C100.05931 (13)0.3205 (5)0.12640 (9)0.0308 (5)
H10A0.01000.29240.15150.037*
H10B0.06860.52160.12270.037*
C110.04212 (14)0.1998 (6)0.06457 (10)0.0379 (6)
H11A0.02550.00420.06860.045*
H11B0.00460.30070.04530.045*
C120.11783 (14)0.2186 (5)0.02536 (10)0.0362 (5)
H12A0.13040.41480.01730.043*
H12B0.10580.12700.01340.043*
C130.19283 (15)0.0828 (5)0.05528 (10)0.0358 (5)
H13A0.24200.10710.02990.043*
H13B0.18250.11750.05950.043*
C140.21039 (13)0.2080 (5)0.11680 (9)0.0317 (5)
H14A0.22610.40410.11210.038*
H14B0.25790.11060.13590.038*
C150.28665 (14)0.9685 (5)0.42765 (10)0.0338 (5)
H15A0.24081.01870.45440.041*
H15B0.31311.14130.41410.041*
C160.34984 (14)0.7987 (5)0.46210 (10)0.0347 (5)
C170.42421 (19)0.7598 (7)0.55380 (13)0.0591 (8)
H17A0.40540.56870.56120.071*
H17B0.47840.75190.53370.071*
C180.4327 (2)0.9083 (9)0.61010 (14)0.0775 (11)
H18A0.45441.09370.60260.116*
H18B0.47110.80880.63690.116*
H18C0.37830.92250.62880.116*
C190.42883 (14)0.6559 (5)0.28894 (12)0.0403 (6)
H19A0.40390.52280.26100.060*
H19B0.43250.57390.32900.060*
H19C0.48460.70460.27570.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0292 (3)0.0237 (3)0.0402 (3)0.0018 (2)0.0030 (2)0.0002 (3)
O10.0286 (8)0.0414 (9)0.0276 (8)0.0026 (7)0.0032 (6)0.0066 (7)
O20.0576 (12)0.0484 (11)0.0531 (11)0.0198 (10)0.0138 (9)0.0149 (10)
O30.0490 (10)0.0465 (11)0.0368 (9)0.0081 (9)0.0149 (8)0.0089 (8)
O4A0.0363 (10)0.0412 (12)0.0402 (11)0.0020 (9)0.0010 (8)0.0072 (9)
O4B0.058 (9)0.030 (7)0.083 (9)0.013 (6)0.001 (8)0.008 (7)
C10.0227 (10)0.0267 (11)0.0302 (10)0.0026 (9)0.0007 (8)0.0023 (9)
C20.0211 (9)0.0254 (11)0.0294 (10)0.0025 (9)0.0000 (8)0.0003 (9)
C30.0242 (10)0.0272 (11)0.0271 (10)0.0014 (9)0.0001 (8)0.0002 (9)
C40.0251 (10)0.0253 (11)0.0266 (10)0.0027 (9)0.0009 (8)0.0011 (9)
C50.0279 (11)0.0319 (12)0.0350 (11)0.0035 (10)0.0028 (9)0.0014 (10)
C60.0267 (10)0.0405 (13)0.0312 (11)0.0049 (10)0.0050 (9)0.0006 (11)
C70.0251 (10)0.0318 (12)0.0279 (10)0.0028 (9)0.0016 (8)0.0043 (10)
C80.0245 (10)0.0308 (12)0.0336 (11)0.0002 (9)0.0002 (9)0.0048 (10)
C90.0313 (11)0.0222 (11)0.0270 (10)0.0006 (9)0.0023 (8)0.0014 (9)
C100.0248 (10)0.0342 (12)0.0335 (11)0.0021 (10)0.0017 (9)0.0003 (10)
C110.0323 (12)0.0469 (15)0.0341 (12)0.0067 (11)0.0080 (9)0.0010 (11)
C120.0384 (12)0.0431 (14)0.0270 (11)0.0051 (11)0.0041 (9)0.0024 (11)
C130.0416 (13)0.0358 (13)0.0301 (11)0.0010 (11)0.0030 (10)0.0049 (11)
C140.0297 (11)0.0350 (12)0.0305 (11)0.0053 (10)0.0016 (9)0.0043 (10)
C150.0338 (11)0.0365 (13)0.0309 (11)0.0016 (10)0.0017 (9)0.0073 (10)
C160.0322 (12)0.0371 (13)0.0346 (12)0.0027 (11)0.0018 (9)0.0044 (11)
C170.0637 (18)0.0570 (18)0.0557 (17)0.0124 (16)0.0278 (15)0.0027 (15)
C180.077 (2)0.102 (3)0.0525 (18)0.025 (2)0.0274 (16)0.0068 (19)
C190.0274 (11)0.0317 (13)0.0620 (16)0.0040 (10)0.0077 (11)0.0001 (12)
Geometric parameters (Å, º) top
S1—O4B1.463 (2)C10—H10A0.9900
S1—O4A1.4641 (19)C10—H10B0.9900
S1—C11.765 (2)C11—C121.517 (3)
S1—C191.780 (2)C11—H11A0.9900
O1—C81.375 (3)C11—H11B0.9900
O1—C71.380 (2)C12—C131.520 (3)
O2—C161.193 (3)C12—H12A0.9900
O3—C161.325 (3)C12—H12B0.9900
O3—C171.460 (3)C13—C141.526 (3)
C1—C81.338 (3)C13—H13A0.9900
C1—C21.439 (3)C13—H13B0.9900
C2—C71.387 (3)C14—H14A0.9900
C2—C31.392 (3)C14—H14B0.9900
C3—C41.391 (3)C15—C161.510 (3)
C3—H30.9500C15—H15A0.9900
C4—C51.399 (3)C15—H15B0.9900
C4—C91.514 (3)C17—C181.455 (4)
C5—C61.385 (3)C17—H17A0.9900
C5—H50.9500C17—H17B0.9900
C6—C71.377 (3)C18—H18A0.9800
C6—H60.9500C18—H18B0.9800
C8—C151.487 (3)C18—H18C0.9800
C9—C141.527 (3)C19—H19A0.9800
C9—C101.533 (3)C19—H19B0.9800
C9—H91.0000C19—H19C0.9800
C10—C111.523 (3)
O4B—S1—O4A119.5 (6)C10—C11—H11B109.3
O4B—S1—C1107.5 (6)H11A—C11—H11B108.0
O4A—S1—C1111.19 (10)C11—C12—C13111.10 (19)
O4B—S1—C19114.0 (6)C11—C12—H12A109.4
O4A—S1—C19105.79 (12)C13—C12—H12A109.4
C1—S1—C1996.58 (11)C11—C12—H12B109.4
C8—O1—C7105.52 (16)C13—C12—H12B109.4
C16—O3—C17116.1 (2)H12A—C12—H12B108.0
C8—C1—C2107.52 (19)C12—C13—C14110.96 (19)
C8—C1—S1122.73 (17)C12—C13—H13A109.4
C2—C1—S1129.54 (16)C14—C13—H13A109.4
C7—C2—C3119.77 (19)C12—C13—H13B109.4
C7—C2—C1104.63 (18)C14—C13—H13B109.4
C3—C2—C1135.6 (2)H13A—C13—H13B108.0
C4—C3—C2118.8 (2)C13—C14—C9111.91 (18)
C4—C3—H3120.6C13—C14—H14A109.2
C2—C3—H3120.6C9—C14—H14A109.2
C3—C4—C5119.3 (2)C13—C14—H14B109.2
C3—C4—C9121.74 (19)C9—C14—H14B109.2
C5—C4—C9118.92 (19)H14A—C14—H14B107.9
C6—C5—C4122.8 (2)C8—C15—C16112.1 (2)
C6—C5—H5118.6C8—C15—H15A109.2
C4—C5—H5118.6C16—C15—H15A109.2
C7—C6—C5116.3 (2)C8—C15—H15B109.2
C7—C6—H6121.9C16—C15—H15B109.2
C5—C6—H6121.9H15A—C15—H15B107.9
C6—C7—O1126.1 (2)O2—C16—O3124.2 (2)
C6—C7—C2123.0 (2)O2—C16—C15125.1 (2)
O1—C7—C2110.79 (18)O3—C16—C15110.7 (2)
C1—C8—O1111.53 (18)C18—C17—O3108.3 (2)
C1—C8—C15133.0 (2)C18—C17—H17A110.0
O1—C8—C15115.31 (19)O3—C17—H17A110.0
C4—C9—C14114.16 (17)C18—C17—H17B110.0
C4—C9—C10110.85 (17)O3—C17—H17B110.0
C14—C9—C10110.00 (18)H17A—C17—H17B108.4
C4—C9—H9107.2C17—C18—H18A109.5
C14—C9—H9107.2C17—C18—H18B109.5
C10—C9—H9107.2H18A—C18—H18B109.5
C11—C10—C9112.27 (19)C17—C18—H18C109.5
C11—C10—H10A109.2H18A—C18—H18C109.5
C9—C10—H10A109.2H18B—C18—H18C109.5
C11—C10—H10B109.2S1—C19—H19A109.5
C9—C10—H10B109.2S1—C19—H19B109.5
H10A—C10—H10B107.9H19A—C19—H19B109.5
C12—C11—C10111.51 (18)S1—C19—H19C109.5
C12—C11—H11A109.3H19A—C19—H19C109.5
C10—C11—H11A109.3H19B—C19—H19C109.5
C12—C11—H11B109.3
O4B—S1—C1—C813.8 (7)C2—C1—C8—O10.8 (2)
O4A—S1—C1—C8146.31 (19)S1—C1—C8—O1174.34 (14)
C19—S1—C1—C8103.9 (2)C2—C1—C8—C15176.7 (2)
O4B—S1—C1—C2172.3 (7)S1—C1—C8—C151.6 (4)
O4A—S1—C1—C239.7 (2)C7—O1—C8—C10.3 (2)
C19—S1—C1—C270.1 (2)C7—O1—C8—C15176.97 (19)
C8—C1—C2—C70.9 (2)C3—C4—C9—C1421.3 (3)
S1—C1—C2—C7173.75 (17)C5—C4—C9—C14160.1 (2)
C8—C1—C2—C3179.9 (2)C3—C4—C9—C10103.6 (2)
S1—C1—C2—C35.4 (4)C5—C4—C9—C1075.0 (2)
C7—C2—C3—C41.0 (3)C4—C9—C10—C11178.72 (18)
C1—C2—C3—C4178.1 (2)C14—C9—C10—C1154.1 (2)
C2—C3—C4—C50.1 (3)C9—C10—C11—C1254.8 (3)
C2—C3—C4—C9178.68 (19)C10—C11—C12—C1355.2 (3)
C3—C4—C5—C60.5 (3)C11—C12—C13—C1455.9 (3)
C9—C4—C5—C6178.2 (2)C12—C13—C14—C956.5 (3)
C4—C5—C6—C70.0 (3)C4—C9—C14—C13179.72 (18)
C5—C6—C7—O1179.3 (2)C10—C9—C14—C1354.9 (2)
C5—C6—C7—C21.0 (3)C1—C8—C15—C1688.6 (3)
C8—O1—C7—C6178.2 (2)O1—C8—C15—C1687.2 (2)
C8—O1—C7—C20.3 (2)C17—O3—C16—O20.5 (4)
C3—C2—C7—C61.5 (3)C17—O3—C16—C15179.5 (2)
C1—C2—C7—C6177.8 (2)C8—C15—C16—O216.1 (3)
C3—C2—C7—O1179.89 (18)C8—C15—C16—O3163.9 (2)
C1—C2—C7—O10.8 (2)C16—O3—C17—C18178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O4Ai0.992.603.479 (3)149
C15—H15B···O2ii0.992.563.437 (3)147
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC19H24O4S
Mr348.45
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)16.1065 (7), 4.8485 (2), 22.3653 (11)
β (°) 91.010 (2)
V3)1746.29 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.28 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.945, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
15388, 3804, 2917
Rint0.049
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.132, 1.02
No. of reflections3804
No. of parameters229
No. of restraints67
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O4Ai0.992.603.479 (3)149
C15—H15B···O2ii0.992.563.437 (3)147
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS Google Scholar
First citationAslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3839.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o3850.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o1826.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGalal, 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
First citationKhan, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSoekamto, 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

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