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

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ISSN: 2056-9890

5-Chloro-3-cyclo­hexyl­sulfinyl-2-methyl-1-benzo­furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 28 February 2011; accepted 2 March 2011; online 9 March 2011)

There are two independent mol­ecules in the asymmetric unit of the title compound, C15H17ClO2S, in each of which the cyclo­hexyl rings adopt chair conformations. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); 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 the structure of 5-bromo-3-cyclo­hexyl­sulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o527.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17ClO2S

  • Mr = 296.80

  • Monoclinic, P 21

  • a = 12.0755 (2) Å

  • b = 9.0033 (2) Å

  • c = 13.9112 (2) Å

  • β = 108.667 (1)°

  • V = 1432.86 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 173 K

  • 0.28 × 0.24 × 0.17 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 = 0.896, Tmax = 0.932

  • 14184 measured reflections

  • 6583 independent reflections

  • 6143 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.084

  • S = 1.03

  • 6583 reflections

  • 345 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.37 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2822 Friedel pairs

  • Flack parameter: 0.03 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯O2i 0.95 2.54 3.469 (3) 166
Symmetry code: (i) 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

Many compounds containing a benzofuran ring exhibit interesting pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006, 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 3-cyclohexylsulfinyl-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2011), we report herein on the crystal structure of the title compound.

The title compound crystallizes as the non-centrosymmetric space group P21 in spite of having no asymmetric C atoms. The asymmetric unit of the title compound is shown in Fig. 1. There are two independent unique molecules [ A & B] in which the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å for A and 0.009 (1) Å for B, respectively, from the least-squares plane defined by the nine constituent atoms. The cyclohexyl rings are in the chair form. The molecular packing is stabilized by weak intermolecular C—H···O hydrogen bonds between a benzene H atom and the O atom of the sulfinyl group (Table 1; C5—H5···O2i).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the structure of 5-bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011).

Experimental top

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclohexylsulfanyl-2-methyl-1-benzofuran (309 mg, 1.1 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 382–383 K; Rf = 0.47 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in aectone 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 and methylene, and 1.5Ueq(C) for methyl H atoms.

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.
5-Chloro-3-cyclohexylsulfinyl-2-methyl-1-benzofuran top
Crystal data top
C15H17ClO2SF(000) = 624
Mr = 296.80Dx = 1.376 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6118 reflections
a = 12.0755 (2) Åθ = 2.7–28.0°
b = 9.0033 (2) ŵ = 0.41 mm1
c = 13.9112 (2) ÅT = 173 K
β = 108.667 (1)°Block, colourless
V = 1432.86 (4) Å30.28 × 0.24 × 0.17 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
6583 independent reflections
Radiation source: rotating anode6143 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.026
Detector resolution: 10.0 pixels mm-1θmax = 28.2°, θmin = 1.6°
ϕ and ω scansh = 1216
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1111
Tmin = 0.896, Tmax = 0.932l = 1816
14184 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.1747P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6583 reflectionsΔρmax = 0.40 e Å3
345 parametersΔρmin = 0.37 e Å3
1 restraintAbsolute structure: Flack (1983), 2822 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (4)
Crystal data top
C15H17ClO2SV = 1432.86 (4) Å3
Mr = 296.80Z = 4
Monoclinic, P21Mo Kα radiation
a = 12.0755 (2) ŵ = 0.41 mm1
b = 9.0033 (2) ÅT = 173 K
c = 13.9112 (2) Å0.28 × 0.24 × 0.17 mm
β = 108.667 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
6583 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6143 reflections with I > 2σ(I)
Tmin = 0.896, Tmax = 0.932Rint = 0.026
14184 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.084Δρmax = 0.40 e Å3
S = 1.03Δρmin = 0.37 e Å3
6583 reflectionsAbsolute structure: Flack (1983), 2822 Friedel pairs
345 parametersAbsolute structure parameter: 0.03 (4)
1 restraint
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.16903 (4)0.32206 (5)0.81418 (3)0.02606 (10)
S20.64550 (4)0.64961 (5)0.83739 (3)0.02826 (10)
Cl10.89697 (5)0.15052 (8)0.68607 (4)0.04851 (15)
Cl20.38281 (5)0.23270 (7)0.69511 (4)0.04830 (15)
O10.09876 (12)0.04307 (17)0.93970 (10)0.0328 (3)
O20.28828 (11)0.33014 (19)0.80366 (11)0.0378 (3)
O30.60633 (12)0.25359 (17)0.94106 (9)0.0301 (3)
O40.75245 (12)0.67789 (19)0.80949 (11)0.0394 (3)
C250.52029 (14)0.6537 (2)0.72146 (12)0.0245 (3)
H250.44930.62360.73890.029*
C10.15225 (15)0.1419 (2)0.85605 (12)0.0232 (4)
C20.19911 (16)0.0065 (2)0.83065 (12)0.0231 (4)
C30.26704 (16)0.0312 (2)0.76970 (13)0.0265 (4)
H30.29210.04130.73150.032*
C40.29587 (16)0.1790 (3)0.76777 (13)0.0312 (4)
C50.26014 (19)0.2885 (2)0.82263 (16)0.0371 (5)
H50.28200.38900.81840.045*
C60.19328 (19)0.2514 (2)0.88290 (17)0.0373 (5)
H60.16850.32390.92120.045*
C70.16438 (17)0.1037 (2)0.88456 (14)0.0272 (4)
C80.09347 (16)0.1064 (2)0.92107 (13)0.0274 (4)
C90.02454 (18)0.1967 (3)0.97107 (15)0.0367 (5)
H9A0.05220.29970.97730.055*
H9B0.05830.19360.93020.055*
H9C0.03430.15631.03870.055*
C100.06561 (15)0.3065 (2)0.68610 (13)0.0273 (4)
H100.08370.21480.65340.033*
C110.0809 (2)0.4417 (3)0.62566 (17)0.0464 (6)
H11A0.07170.53360.66140.056*
H11B0.16030.44140.61950.056*
C120.0104 (3)0.4381 (4)0.52011 (19)0.0577 (7)
H12A0.00330.35000.48280.069*
H12B0.00170.52770.48190.069*
C130.1333 (2)0.4322 (3)0.52604 (18)0.0524 (7)
H13A0.19020.42800.45670.063*
H13B0.14900.52340.55930.063*
C140.14857 (19)0.2984 (3)0.58510 (17)0.0507 (7)
H14A0.22790.29960.59140.061*
H14B0.14110.20730.54790.061*
C150.05747 (17)0.2951 (3)0.69140 (15)0.0415 (6)
H15A0.06560.20150.72590.050*
H15B0.07200.37880.73200.050*
C160.64528 (16)0.4596 (2)0.86753 (13)0.0252 (4)
C170.70239 (16)0.3378 (2)0.83536 (13)0.0240 (4)
C180.77230 (16)0.3203 (2)0.77357 (13)0.0272 (4)
H180.79360.40250.74050.033*
C190.80929 (15)0.1776 (3)0.76261 (13)0.0315 (4)
C200.77837 (19)0.0540 (2)0.80917 (16)0.0358 (5)
H200.80420.04210.79790.043*
C210.71070 (19)0.0711 (2)0.87124 (16)0.0345 (5)
H210.68970.01130.90440.041*
C220.67472 (16)0.2129 (2)0.88309 (13)0.0279 (4)
C230.59106 (17)0.4040 (2)0.93076 (13)0.0283 (4)
C240.52066 (19)0.4726 (3)0.98873 (15)0.0405 (5)
H24A0.43890.47960.94550.061*
H24B0.55070.57231.01080.061*
H24C0.52580.41141.04820.061*
C260.53191 (17)0.5501 (2)0.63839 (13)0.0274 (4)
H26A0.53810.44600.66240.033*
H26B0.60380.57460.62200.033*
C270.42505 (18)0.5671 (3)0.54340 (14)0.0346 (5)
H27A0.43420.50240.48890.042*
H27B0.35420.53480.55880.042*
C280.4101 (2)0.7270 (3)0.50687 (15)0.0385 (5)
H28A0.47820.75700.48640.046*
H28B0.33910.73550.44680.046*
C290.39932 (19)0.8293 (3)0.58943 (15)0.0374 (5)
H29A0.32720.80480.60540.045*
H29B0.39270.93320.56490.045*
C300.50495 (17)0.8157 (2)0.68588 (14)0.0319 (4)
H30A0.49320.87920.73990.038*
H30B0.57630.84990.67200.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0268 (2)0.0196 (2)0.0307 (2)0.00028 (18)0.00769 (16)0.00088 (17)
S20.0304 (2)0.0215 (2)0.0281 (2)0.00027 (18)0.00275 (16)0.00124 (18)
Cl10.0433 (3)0.0614 (4)0.0446 (3)0.0168 (3)0.0194 (2)0.0047 (3)
Cl20.0514 (3)0.0471 (3)0.0473 (3)0.0212 (3)0.0171 (2)0.0081 (2)
O10.0322 (7)0.0364 (8)0.0313 (7)0.0029 (6)0.0121 (6)0.0073 (6)
O20.0282 (7)0.0361 (8)0.0478 (7)0.0054 (7)0.0102 (6)0.0047 (7)
O30.0315 (7)0.0319 (8)0.0278 (6)0.0040 (6)0.0106 (5)0.0038 (6)
O40.0300 (7)0.0308 (8)0.0520 (8)0.0038 (7)0.0057 (6)0.0082 (7)
C250.0213 (7)0.0260 (9)0.0248 (7)0.0015 (7)0.0055 (6)0.0004 (7)
C10.0213 (8)0.0227 (9)0.0246 (8)0.0002 (7)0.0058 (7)0.0012 (7)
C20.0226 (9)0.0206 (9)0.0230 (8)0.0006 (7)0.0031 (7)0.0018 (6)
C30.0261 (9)0.0253 (10)0.0264 (8)0.0021 (7)0.0059 (7)0.0002 (7)
C40.0296 (9)0.0308 (10)0.0290 (8)0.0055 (9)0.0036 (7)0.0054 (8)
C50.0379 (12)0.0201 (10)0.0435 (11)0.0024 (8)0.0009 (10)0.0018 (8)
C60.0363 (11)0.0256 (11)0.0448 (12)0.0038 (9)0.0055 (9)0.0095 (9)
C70.0251 (9)0.0267 (10)0.0277 (9)0.0023 (7)0.0054 (7)0.0025 (7)
C80.0253 (9)0.0316 (10)0.0236 (8)0.0013 (8)0.0056 (7)0.0008 (7)
C90.0314 (10)0.0496 (14)0.0301 (9)0.0014 (10)0.0113 (8)0.0075 (9)
C100.0277 (9)0.0253 (10)0.0283 (8)0.0013 (7)0.0083 (7)0.0033 (7)
C110.0475 (13)0.0450 (14)0.0436 (11)0.0055 (11)0.0099 (10)0.0172 (10)
C120.0657 (17)0.0612 (18)0.0415 (13)0.0002 (14)0.0105 (12)0.0215 (12)
C130.0524 (15)0.0524 (16)0.0398 (12)0.0197 (12)0.0031 (10)0.0041 (11)
C140.0266 (10)0.073 (2)0.0454 (12)0.0056 (11)0.0022 (9)0.0035 (12)
C150.0268 (10)0.0604 (17)0.0372 (10)0.0027 (10)0.0103 (8)0.0071 (10)
C160.0277 (9)0.0224 (9)0.0229 (8)0.0001 (7)0.0045 (7)0.0010 (7)
C170.0239 (9)0.0208 (9)0.0242 (8)0.0004 (7)0.0034 (7)0.0006 (7)
C180.0262 (9)0.0286 (10)0.0248 (8)0.0010 (8)0.0055 (7)0.0020 (7)
C190.0260 (8)0.0382 (11)0.0282 (8)0.0071 (9)0.0056 (7)0.0021 (9)
C200.0367 (12)0.0236 (10)0.0394 (11)0.0055 (9)0.0017 (9)0.0021 (8)
C210.0378 (12)0.0220 (10)0.0384 (10)0.0032 (8)0.0050 (9)0.0048 (8)
C220.0256 (9)0.0305 (11)0.0247 (8)0.0043 (8)0.0041 (7)0.0036 (7)
C230.0263 (9)0.0321 (10)0.0229 (8)0.0022 (8)0.0029 (7)0.0027 (7)
C240.0330 (12)0.0583 (16)0.0319 (10)0.0009 (10)0.0128 (8)0.0094 (10)
C260.0311 (10)0.0235 (9)0.0274 (8)0.0008 (7)0.0089 (7)0.0016 (7)
C270.0363 (11)0.0354 (12)0.0270 (9)0.0011 (9)0.0030 (8)0.0049 (8)
C280.0405 (12)0.0407 (13)0.0280 (9)0.0041 (10)0.0021 (8)0.0046 (9)
C290.0369 (11)0.0328 (12)0.0362 (10)0.0100 (9)0.0029 (8)0.0047 (9)
C300.0333 (10)0.0243 (10)0.0330 (9)0.0055 (8)0.0036 (8)0.0005 (8)
Geometric parameters (Å, º) top
S1—O21.4951 (13)C12—H12B0.9900
S1—C11.7569 (19)C13—C141.502 (4)
S1—C101.8246 (17)C13—H13A0.9900
S2—O41.4847 (15)C13—H13B0.9900
S2—C161.762 (2)C14—C151.535 (3)
S2—C251.8241 (16)C14—H14A0.9900
Cl1—C191.7424 (18)C14—H14B0.9900
Cl2—C41.7427 (19)C15—H15A0.9900
O1—C81.368 (3)C15—H15B0.9900
O1—C71.380 (2)C16—C231.350 (3)
O3—C231.368 (3)C16—C171.441 (3)
O3—C221.376 (2)C17—C181.393 (3)
C25—C261.526 (2)C17—C221.400 (3)
C25—C301.532 (3)C18—C191.385 (3)
C25—H251.0000C18—H180.9500
C1—C81.355 (2)C19—C201.397 (3)
C1—C21.435 (3)C20—C211.374 (3)
C2—C71.387 (3)C20—H200.9500
C2—C31.397 (3)C21—C221.376 (3)
C3—C41.377 (3)C21—H210.9500
C3—H30.9500C23—C241.481 (3)
C4—C51.397 (3)C24—H24A0.9800
C5—C61.378 (3)C24—H24B0.9800
C5—H50.9500C24—H24C0.9800
C6—C71.377 (3)C26—C271.531 (2)
C6—H60.9500C26—H26A0.9900
C8—C91.486 (3)C26—H26B0.9900
C9—H9A0.9800C27—C281.518 (3)
C9—H9B0.9800C27—H27A0.9900
C9—H9C0.9800C27—H27B0.9900
C10—C151.515 (3)C28—C291.510 (3)
C10—C111.523 (3)C28—H28A0.9900
C10—H101.0000C28—H28B0.9900
C11—C121.528 (3)C29—C301.532 (3)
C11—H11A0.9900C29—H29A0.9900
C11—H11B0.9900C29—H29B0.9900
C12—C131.514 (4)C30—H30A0.9900
C12—H12A0.9900C30—H30B0.9900
O2—S1—C1107.11 (9)C15—C14—H14A109.3
O2—S1—C10106.72 (8)C13—C14—H14B109.3
C1—S1—C1097.91 (8)C15—C14—H14B109.3
O4—S2—C16107.24 (9)H14A—C14—H14B108.0
O4—S2—C25108.04 (8)C10—C15—C14111.32 (17)
C16—S2—C2599.55 (9)C10—C15—H15A109.4
C8—O1—C7106.52 (14)C14—C15—H15A109.4
C23—O3—C22106.75 (14)C10—C15—H15B109.4
C26—C25—C30111.59 (14)C14—C15—H15B109.4
C26—C25—S2113.96 (12)H15A—C15—H15B108.0
C30—C25—S2106.56 (13)C23—C16—C17107.50 (17)
C26—C25—H25108.2C23—C16—S2123.58 (15)
C30—C25—H25108.2C17—C16—S2128.89 (14)
S2—C25—H25108.2C18—C17—C22119.04 (18)
C8—C1—C2107.22 (17)C18—C17—C16136.28 (18)
C8—C1—S1125.45 (15)C22—C17—C16104.67 (16)
C2—C1—S1127.32 (13)C19—C18—C17116.97 (18)
C7—C2—C3119.46 (18)C19—C18—H18121.5
C7—C2—C1105.27 (16)C17—C18—H18121.5
C3—C2—C1135.26 (17)C18—C19—C20122.98 (18)
C4—C3—C2116.61 (18)C18—C19—Cl1118.53 (16)
C4—C3—H3121.7C20—C19—Cl1118.49 (17)
C2—C3—H3121.7C21—C20—C19120.23 (19)
C3—C4—C5123.14 (18)C21—C20—H20119.9
C3—C4—Cl2118.84 (16)C19—C20—H20119.9
C5—C4—Cl2118.02 (17)C20—C21—C22116.94 (19)
C6—C5—C4120.3 (2)C20—C21—H21121.5
C6—C5—H5119.8C22—C21—H21121.5
C4—C5—H5119.8C21—C22—O3126.10 (17)
C7—C6—C5116.4 (2)C21—C22—C17123.81 (18)
C7—C6—H6121.8O3—C22—C17110.08 (17)
C5—C6—H6121.8C16—C23—O3110.98 (17)
C6—C7—O1125.83 (18)C16—C23—C24133.1 (2)
C6—C7—C2124.0 (2)O3—C23—C24115.93 (18)
O1—C7—C2110.13 (17)C23—C24—H24A109.5
C1—C8—O1110.86 (17)C23—C24—H24B109.5
C1—C8—C9132.5 (2)H24A—C24—H24B109.5
O1—C8—C9116.66 (17)C23—C24—H24C109.5
C8—C9—H9A109.5H24A—C24—H24C109.5
C8—C9—H9B109.5H24B—C24—H24C109.5
H9A—C9—H9B109.5C25—C26—C27109.65 (15)
C8—C9—H9C109.5C25—C26—H26A109.7
H9A—C9—H9C109.5C27—C26—H26A109.7
H9B—C9—H9C109.5C25—C26—H26B109.7
C15—C10—C11112.03 (18)C27—C26—H26B109.7
C15—C10—S1109.46 (13)H26A—C26—H26B108.2
C11—C10—S1108.18 (14)C28—C27—C26111.15 (17)
C15—C10—H10109.0C28—C27—H27A109.4
C11—C10—H10109.0C26—C27—H27A109.4
S1—C10—H10109.0C28—C27—H27B109.4
C10—C11—C12109.6 (2)C26—C27—H27B109.4
C10—C11—H11A109.7H27A—C27—H27B108.0
C12—C11—H11A109.7C29—C28—C27110.74 (17)
C10—C11—H11B109.7C29—C28—H28A109.5
C12—C11—H11B109.7C27—C28—H28A109.5
H11A—C11—H11B108.2C29—C28—H28B109.5
C13—C12—C11111.5 (2)C27—C28—H28B109.5
C13—C12—H12A109.3H28A—C28—H28B108.1
C11—C12—H12A109.3C28—C29—C30111.53 (17)
C13—C12—H12B109.3C28—C29—H29A109.3
C11—C12—H12B109.3C30—C29—H29A109.3
H12A—C12—H12B108.0C28—C29—H29B109.3
C14—C13—C12110.6 (2)C30—C29—H29B109.3
C14—C13—H13A109.5H29A—C29—H29B108.0
C12—C13—H13A109.5C29—C30—C25109.89 (17)
C14—C13—H13B109.5C29—C30—H30A109.7
C12—C13—H13B109.5C25—C30—H30A109.7
H13A—C13—H13B108.1C29—C30—H30B109.7
C13—C14—C15111.5 (2)C25—C30—H30B109.7
C13—C14—H14A109.3H30A—C30—H30B108.2
O4—S2—C25—C2653.45 (16)C12—C13—C14—C1555.9 (3)
C16—S2—C25—C2658.32 (15)C11—C10—C15—C1454.0 (3)
O4—S2—C25—C3070.08 (14)S1—C10—C15—C14174.00 (17)
C16—S2—C25—C30178.15 (12)C13—C14—C15—C1054.1 (3)
O2—S1—C1—C8144.40 (16)O4—S2—C16—C23153.83 (16)
C10—S1—C1—C8105.31 (17)C25—S2—C16—C2393.78 (17)
O2—S1—C1—C234.12 (18)O4—S2—C16—C1723.87 (19)
C10—S1—C1—C276.16 (17)C25—S2—C16—C1788.52 (18)
C8—C1—C2—C70.3 (2)C23—C16—C17—C18178.8 (2)
S1—C1—C2—C7178.40 (14)S2—C16—C17—C180.8 (3)
C8—C1—C2—C3179.4 (2)C23—C16—C17—C221.0 (2)
S1—C1—C2—C30.6 (3)S2—C16—C17—C22178.94 (14)
C7—C2—C3—C40.3 (3)C22—C17—C18—C190.7 (3)
C1—C2—C3—C4178.63 (19)C16—C17—C18—C19179.6 (2)
C2—C3—C4—C50.3 (3)C17—C18—C19—C200.8 (3)
C2—C3—C4—Cl2178.79 (13)C17—C18—C19—Cl1179.97 (13)
C3—C4—C5—C60.4 (3)C18—C19—C20—C211.7 (3)
Cl2—C4—C5—C6178.68 (16)Cl1—C19—C20—C21179.09 (15)
C4—C5—C6—C70.5 (3)C19—C20—C21—C221.0 (3)
C5—C6—C7—O1179.82 (17)C20—C21—C22—O3179.60 (17)
C5—C6—C7—C20.5 (3)C20—C21—C22—C170.5 (3)
C8—O1—C7—C6178.7 (2)C23—O3—C22—C21179.5 (2)
C8—O1—C7—C20.7 (2)C23—O3—C22—C170.34 (19)
C3—C2—C7—C60.4 (3)C18—C17—C22—C211.4 (3)
C1—C2—C7—C6178.8 (2)C16—C17—C22—C21178.85 (19)
C3—C2—C7—O1179.83 (16)C18—C17—C22—O3179.42 (15)
C1—C2—C7—O10.6 (2)C16—C17—C22—O30.37 (19)
C2—C1—C8—O10.0 (2)C17—C16—C23—O31.2 (2)
S1—C1—C8—O1178.82 (13)S2—C16—C23—O3179.34 (13)
C2—C1—C8—C9178.08 (19)C17—C16—C23—C24178.90 (19)
S1—C1—C8—C93.1 (3)S2—C16—C23—C240.8 (3)
C7—O1—C8—C10.4 (2)C22—O3—C23—C161.0 (2)
C7—O1—C8—C9178.81 (16)C22—O3—C23—C24179.11 (16)
O2—S1—C10—C15179.02 (15)C30—C25—C26—C2756.8 (2)
C1—S1—C10—C1568.41 (16)S2—C25—C26—C27177.59 (14)
O2—S1—C10—C1158.67 (17)C25—C26—C27—C2857.1 (2)
C1—S1—C10—C11169.27 (15)C26—C27—C28—C2957.4 (2)
C15—C10—C11—C1255.3 (3)C27—C28—C29—C3056.8 (3)
S1—C10—C11—C12175.99 (18)C28—C29—C30—C2555.9 (2)
C10—C11—C12—C1357.2 (3)C26—C25—C30—C2956.2 (2)
C11—C12—C13—C1458.1 (3)S2—C25—C30—C29178.84 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.952.543.469 (3)166
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H17ClO2S
Mr296.80
Crystal system, space groupMonoclinic, P21
Temperature (K)173
a, b, c (Å)12.0755 (2), 9.0033 (2), 13.9112 (2)
β (°) 108.667 (1)
V3)1432.86 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.28 × 0.24 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.896, 0.932
No. of measured, independent and
observed [I > 2σ(I)] reflections
14184, 6583, 6143
Rint0.026
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.084, 1.03
No. of reflections6583
No. of parameters345
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.37
Absolute structureFlack (1983), 2822 Friedel pairs
Absolute structure parameter0.03 (4)

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
C5—H5···O2i0.952.543.469 (3)166
Symmetry code: (i) x, y+1, z.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS
First citationAslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226.  Web of Science CrossRef CAS
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o527.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
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
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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
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

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