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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Bromo-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 18 January 2011; accepted 25 January 2011; online 29 January 2011)

In the asymmetric unit of the title compound, C15H17BrO3S, there are two independent mol­ecules. The cyclo­hexane rings in each adopt classic chair conformations. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds and aromatic ππ inter­actions between the furan rings of symmetry-related mol­ecules [centroid–centroid distance = 3.555 (2) Å].

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 related structures, see: Choi et al. (2007[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o521-o522.]); Seo et al. (2009[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2302.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17BrO2S

  • Mr = 341.26

  • Monoclinic, P 21 /c

  • a = 12.1842 (2) Å

  • b = 9.0281 (1) Å

  • c = 26.6191 (4) Å

  • β = 97.702 (1)°

  • V = 2901.69 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.97 mm−1

  • T = 173 K

  • 0.31 × 0.22 × 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 = 0.579, Tmax = 0.746

  • 26831 measured reflections

  • 6674 independent reflections

  • 4944 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.088

  • S = 1.04

  • 6674 reflections

  • 345 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯O2i 0.95 2.56 3.495 (3) 170
C25—H25⋯O2 1.00 2.57 3.409 (3) 142
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 involving a benzofuran ring have potential 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 5-bromo-2-methyl-3-methylsufinyl-1-benzofuran analogues (Choi et al., 2007, Seo et al., 2009), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. There are two independent molecules [A and B] in which the benzofuran unit is essentially planar in each with a mean deviation of 0.013 (2) Å and 0.014 (2) Å for A and B, respectively from the least-squares plane defined by the nine constituent atoms. The cyclohexyl rings are in the chair form. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the oxygen atom of the SO unit (Table 1; C5—H5···O2i), and the second one between a cyclohexyl H atom and the oxygen atom of the SO unit (Table 1; C25—H25···O2). An intramolecular hydrogen bond exists between a cyclohexyl H atom and the oxygen atom of the SO unit (Table 1; C25—H25···O2). Further stabilization is provided by aromatic ππ interactions between the furan rings of symmetry related molecules, with a Cg1···Cg2(1-x,1/2+y,3/2-z) distance of 3.555 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 and C16/C17/C22/O3/C23 furan rings, respectively).

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 related structures, see: Choi et al. (2007); Seo et al. (2009).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-cyclohexylsulfanyl-2-methyl-1-benzofuran (293 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, 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 72%, m.p. 388–389 K; Rf = 0.45 (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 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 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 displacement ellipsoids drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O and ππ interactions (dotted lines) in the crystal packing of the title compound. [Symmetry codes: (i) x, y + 1, z; (ii) - x + 1, y + 1/2, - z + 3/2; (iii) x, - 1 +y,z .]
5-Bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran top
Crystal data top
C15H17BrO2SF(000) = 1392
Mr = 341.26Dx = 1.562 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7002 reflections
a = 12.1842 (2) Åθ = 2.4–24.9°
b = 9.0281 (1) ŵ = 2.97 mm1
c = 26.6191 (4) ÅT = 173 K
β = 97.702 (1)°Block, colourless
V = 2901.69 (7) Å30.31 × 0.22 × 0.18 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD
diffractometer
6674 independent reflections
Radiation source: rotating anode4944 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.041
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.5°
ϕ and ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1011
Tmin = 0.579, Tmax = 0.746l = 3234
26831 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)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.088H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1726P]
where P = (Fo2 + 2Fc2)/3
6674 reflections(Δ/σ)max = 0.001
345 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.56 e Å3
Crystal data top
C15H17BrO2SV = 2901.69 (7) Å3
Mr = 341.26Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.1842 (2) ŵ = 2.97 mm1
b = 9.0281 (1) ÅT = 173 K
c = 26.6191 (4) Å0.31 × 0.22 × 0.18 mm
β = 97.702 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
6674 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
4944 reflections with I > 2σ(I)
Tmin = 0.579, Tmax = 0.746Rint = 0.041
26831 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.04Δρmax = 0.41 e Å3
6674 reflectionsΔρmin = 0.56 e Å3
345 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*/Ueq
Br10.46756 (2)0.86266 (3)0.592298 (11)0.04012 (9)
Br20.07658 (2)0.22211 (3)0.590592 (11)0.04406 (10)
S10.73629 (5)0.29635 (6)0.65910 (2)0.02434 (14)
S20.27538 (5)0.26776 (7)0.66785 (2)0.02864 (15)
O10.87123 (13)0.65573 (18)0.72524 (6)0.0277 (4)
O20.61309 (14)0.28891 (19)0.65360 (7)0.0350 (4)
O30.36105 (14)0.13307 (18)0.71689 (6)0.0313 (4)
O40.15602 (15)0.3032 (2)0.65511 (7)0.0401 (5)
C10.77497 (18)0.4739 (2)0.68179 (8)0.0211 (5)
C20.71675 (18)0.6108 (2)0.66932 (8)0.0202 (5)
C30.62204 (19)0.6512 (3)0.63733 (8)0.0230 (5)
H30.57770.58030.61750.028*
C40.59557 (19)0.8007 (3)0.63584 (9)0.0250 (5)
C50.6577 (2)0.9072 (3)0.66440 (9)0.0299 (6)
H50.63571.00820.66190.036*
C60.7517 (2)0.8665 (3)0.69656 (9)0.0294 (6)
H60.79510.93710.71690.035*
C70.77938 (19)0.7179 (3)0.69753 (9)0.0239 (5)
C80.86624 (19)0.5065 (3)0.71497 (8)0.0249 (5)
C90.9604 (2)0.4162 (3)0.73881 (10)0.0353 (6)
H9A0.93660.31310.74130.053*
H9B0.98600.45460.77280.053*
H9C1.02100.42100.71810.053*
C100.77442 (19)0.3168 (3)0.59584 (9)0.0234 (5)
H100.74060.41000.58050.028*
C110.8996 (2)0.3278 (3)0.59887 (10)0.0394 (7)
H11A0.93430.24110.61740.047*
H11B0.92570.41820.61790.047*
C120.9348 (3)0.3334 (4)0.54597 (12)0.0561 (9)
H12A0.90790.42660.52900.067*
H12B1.01660.33270.54890.067*
C130.8886 (3)0.2023 (4)0.51411 (12)0.0612 (10)
H13A0.90920.21130.47950.073*
H13B0.92110.10940.52930.073*
C140.7638 (3)0.1964 (3)0.51127 (10)0.0487 (8)
H14A0.73540.10950.49090.058*
H14B0.73130.28660.49410.058*
C150.7284 (2)0.1857 (3)0.56366 (10)0.0380 (6)
H15A0.75610.09200.58010.046*
H15B0.64650.18530.56080.046*
C160.28708 (19)0.0766 (3)0.68148 (8)0.0242 (5)
C170.2120 (2)0.0437 (3)0.66480 (9)0.0245 (5)
C180.11013 (19)0.0572 (3)0.63480 (8)0.0255 (5)
H180.07300.02640.61890.031*
C190.0653 (2)0.1977 (3)0.62917 (9)0.0294 (6)
C200.1191 (2)0.3231 (3)0.65164 (10)0.0344 (6)
H200.08600.41800.64610.041*
C210.2188 (2)0.3094 (3)0.68142 (10)0.0343 (6)
H210.25620.39300.69720.041*
C220.2629 (2)0.1690 (3)0.68765 (9)0.0264 (5)
C230.3726 (2)0.0180 (3)0.71287 (9)0.0280 (5)
C240.4728 (2)0.0833 (3)0.74241 (10)0.0409 (7)
H24A0.53450.07920.72230.061*
H24B0.49210.02720.77390.061*
H24C0.45810.18670.75050.061*
C250.33763 (19)0.2705 (2)0.60925 (8)0.0228 (5)
H250.41330.22600.61650.027*
C260.3509 (2)0.4326 (3)0.59471 (9)0.0308 (6)
H26A0.27730.48080.58880.037*
H26B0.39630.48530.62280.037*
C270.4067 (2)0.4425 (3)0.54673 (9)0.0332 (6)
H27A0.41250.54760.53690.040*
H27B0.48250.40150.55360.040*
C280.3413 (2)0.3575 (3)0.50351 (10)0.0354 (6)
H28A0.38030.36270.47320.043*
H28B0.26750.40350.49480.043*
C290.3274 (2)0.1960 (3)0.51799 (9)0.0320 (6)
H29A0.40090.14740.52330.038*
H29B0.28130.14420.48990.038*
C300.2729 (2)0.1827 (3)0.56638 (9)0.0268 (5)
H30A0.19600.22040.55990.032*
H30B0.27000.07720.57630.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03958 (16)0.03535 (16)0.04353 (17)0.01601 (13)0.00135 (12)0.00518 (12)
Br20.03332 (16)0.0532 (2)0.04619 (18)0.01426 (14)0.00714 (13)0.00397 (14)
S10.0269 (3)0.0171 (3)0.0293 (3)0.0007 (2)0.0049 (2)0.0014 (2)
S20.0371 (4)0.0203 (3)0.0308 (3)0.0019 (3)0.0129 (3)0.0023 (3)
O10.0235 (9)0.0308 (9)0.0279 (9)0.0036 (7)0.0006 (7)0.0047 (7)
O20.0271 (9)0.0309 (10)0.0486 (11)0.0076 (8)0.0112 (8)0.0029 (8)
O30.0353 (10)0.0293 (10)0.0293 (9)0.0065 (8)0.0042 (8)0.0044 (7)
O40.0382 (11)0.0323 (10)0.0534 (12)0.0061 (9)0.0198 (9)0.0080 (9)
C10.0218 (11)0.0199 (12)0.0220 (12)0.0012 (9)0.0039 (9)0.0018 (9)
C20.0228 (11)0.0183 (11)0.0208 (11)0.0000 (9)0.0082 (9)0.0006 (9)
C30.0247 (12)0.0204 (12)0.0241 (12)0.0001 (10)0.0042 (10)0.0001 (10)
C40.0259 (13)0.0246 (13)0.0254 (12)0.0037 (10)0.0072 (10)0.0033 (10)
C50.0348 (14)0.0185 (12)0.0387 (15)0.0010 (11)0.0134 (12)0.0005 (11)
C60.0327 (14)0.0230 (13)0.0335 (14)0.0071 (11)0.0084 (11)0.0091 (11)
C70.0210 (12)0.0294 (13)0.0216 (12)0.0024 (10)0.0042 (9)0.0036 (10)
C80.0259 (12)0.0292 (13)0.0199 (12)0.0012 (10)0.0044 (9)0.0018 (10)
C90.0253 (13)0.0486 (16)0.0312 (14)0.0070 (12)0.0008 (11)0.0059 (12)
C100.0250 (12)0.0206 (12)0.0248 (12)0.0030 (10)0.0039 (10)0.0004 (9)
C110.0257 (14)0.0558 (18)0.0375 (15)0.0042 (13)0.0071 (12)0.0041 (13)
C120.0397 (17)0.086 (2)0.0462 (19)0.0061 (18)0.0204 (14)0.0000 (18)
C130.085 (3)0.065 (2)0.0386 (18)0.024 (2)0.0271 (18)0.0063 (16)
C140.076 (2)0.0350 (16)0.0340 (16)0.0026 (16)0.0017 (15)0.0115 (13)
C150.0502 (17)0.0280 (14)0.0344 (15)0.0021 (13)0.0009 (13)0.0073 (12)
C160.0299 (13)0.0203 (12)0.0240 (12)0.0002 (10)0.0091 (10)0.0014 (10)
C170.0309 (13)0.0211 (12)0.0235 (12)0.0006 (10)0.0110 (10)0.0026 (10)
C180.0289 (13)0.0240 (13)0.0247 (13)0.0003 (10)0.0074 (10)0.0036 (10)
C190.0293 (13)0.0330 (14)0.0273 (13)0.0056 (11)0.0089 (10)0.0039 (11)
C200.0456 (17)0.0212 (13)0.0396 (16)0.0063 (12)0.0168 (13)0.0025 (11)
C210.0450 (16)0.0210 (13)0.0397 (16)0.0053 (12)0.0163 (13)0.0062 (11)
C220.0292 (13)0.0255 (13)0.0255 (13)0.0035 (11)0.0077 (10)0.0014 (10)
C230.0300 (13)0.0291 (13)0.0264 (13)0.0010 (11)0.0097 (10)0.0024 (11)
C240.0311 (14)0.0576 (18)0.0338 (15)0.0026 (14)0.0037 (12)0.0087 (14)
C250.0241 (12)0.0208 (12)0.0243 (12)0.0005 (10)0.0056 (10)0.0000 (10)
C260.0340 (14)0.0230 (13)0.0373 (15)0.0050 (11)0.0115 (11)0.0014 (11)
C270.0388 (15)0.0271 (14)0.0354 (15)0.0052 (12)0.0107 (12)0.0047 (11)
C280.0452 (16)0.0323 (15)0.0292 (14)0.0009 (13)0.0065 (12)0.0069 (11)
C290.0430 (16)0.0286 (14)0.0239 (13)0.0014 (12)0.0028 (11)0.0005 (11)
C300.0303 (13)0.0208 (12)0.0290 (13)0.0037 (10)0.0027 (10)0.0011 (10)
Geometric parameters (Å, º) top
Br1—C41.899 (2)C13—H13B0.9900
Br2—C191.902 (3)C14—C151.517 (4)
S1—O21.4901 (18)C14—H14A0.9900
S1—C11.755 (2)C14—H14B0.9900
S1—C101.815 (2)C15—H15A0.9900
S2—O41.483 (2)C15—H15B0.9900
S2—C161.765 (2)C16—C231.353 (3)
S2—C251.824 (2)C16—C171.451 (3)
O1—C81.374 (3)C17—C181.388 (3)
O1—C71.375 (3)C17—C221.390 (3)
O3—C221.376 (3)C18—C191.382 (3)
O3—C231.377 (3)C18—H180.9500
C1—C81.357 (3)C19—C201.401 (4)
C1—C21.442 (3)C20—C211.364 (4)
C2—C31.388 (3)C20—H200.9500
C2—C71.388 (3)C21—C221.378 (3)
C3—C41.387 (3)C21—H210.9500
C3—H30.9500C23—C241.483 (3)
C4—C51.386 (3)C24—H24A0.9800
C5—C61.385 (4)C24—H24B0.9800
C5—H50.9500C24—H24C0.9800
C6—C71.383 (3)C25—C301.521 (3)
C6—H60.9500C25—C261.528 (3)
C8—C91.480 (3)C25—H251.0000
C9—H9A0.9800C26—C271.528 (3)
C9—H9B0.9800C26—H26A0.9900
C9—H9C0.9800C26—H26B0.9900
C10—C111.520 (3)C27—C281.517 (4)
C10—C151.524 (3)C27—H27A0.9900
C10—H101.0000C27—H27B0.9900
C11—C121.527 (4)C28—C291.523 (3)
C11—H11A0.9900C28—H28A0.9900
C11—H11B0.9900C28—H28B0.9900
C12—C131.519 (5)C29—C301.532 (3)
C12—H12A0.9900C29—H29A0.9900
C12—H12B0.9900C29—H29B0.9900
C13—C141.513 (5)C30—H30A0.9900
C13—H13A0.9900C30—H30B0.9900
O2—S1—C1107.19 (10)C10—C15—H15A109.7
O2—S1—C10107.04 (11)C14—C15—H15B109.7
C1—S1—C1097.81 (11)C10—C15—H15B109.7
O4—S2—C16107.92 (11)H15A—C15—H15B108.2
O4—S2—C25107.99 (11)C23—C16—C17107.3 (2)
C16—S2—C2599.08 (10)C23—C16—S2122.95 (19)
C8—O1—C7106.39 (17)C17—C16—S2129.71 (18)
C22—O3—C23106.25 (18)C18—C17—C22119.5 (2)
C8—C1—C2107.4 (2)C18—C17—C16136.0 (2)
C8—C1—S1125.56 (18)C22—C17—C16104.4 (2)
C2—C1—S1127.08 (17)C19—C18—C17116.9 (2)
C3—C2—C7120.1 (2)C19—C18—H18121.6
C3—C2—C1135.2 (2)C17—C18—H18121.6
C7—C2—C1104.76 (19)C18—C19—C20122.7 (2)
C4—C3—C2116.4 (2)C18—C19—Br2118.84 (19)
C4—C3—H3121.8C20—C19—Br2118.43 (19)
C2—C3—H3121.8C21—C20—C19120.2 (2)
C5—C4—C3123.5 (2)C21—C20—H20119.9
C5—C4—Br1118.29 (18)C19—C20—H20119.9
C3—C4—Br1118.24 (18)C20—C21—C22117.1 (2)
C6—C5—C4120.1 (2)C20—C21—H21121.4
C6—C5—H5120.0C22—C21—H21121.4
C4—C5—H5120.0O3—C22—C21125.5 (2)
C7—C6—C5116.6 (2)O3—C22—C17111.0 (2)
C7—C6—H6121.7C21—C22—C17123.5 (2)
C5—C6—H6121.7C16—C23—O3111.0 (2)
O1—C7—C6125.8 (2)C16—C23—C24133.1 (2)
O1—C7—C2110.8 (2)O3—C23—C24116.0 (2)
C6—C7—C2123.4 (2)C23—C24—H24A109.5
C1—C8—O1110.7 (2)C23—C24—H24B109.5
C1—C8—C9132.9 (2)H24A—C24—H24B109.5
O1—C8—C9116.4 (2)C23—C24—H24C109.5
C8—C9—H9A109.5H24A—C24—H24C109.5
C8—C9—H9B109.5H24B—C24—H24C109.5
H9A—C9—H9B109.5C30—C25—C26111.8 (2)
C8—C9—H9C109.5C30—C25—S2113.65 (16)
H9A—C9—H9C109.5C26—C25—S2107.45 (15)
H9B—C9—H9C109.5C30—C25—H25107.9
C11—C10—C15111.8 (2)C26—C25—H25107.9
C11—C10—S1109.71 (17)S2—C25—H25107.9
C15—C10—S1108.77 (17)C27—C26—C25110.0 (2)
C11—C10—H10108.8C27—C26—H26A109.7
C15—C10—H10108.8C25—C26—H26A109.7
S1—C10—H10108.8C27—C26—H26B109.7
C10—C11—C12110.9 (2)C25—C26—H26B109.7
C10—C11—H11A109.5H26A—C26—H26B108.2
C12—C11—H11A109.5C28—C27—C26110.9 (2)
C10—C11—H11B109.5C28—C27—H27A109.4
C12—C11—H11B109.5C26—C27—H27A109.4
H11A—C11—H11B108.0C28—C27—H27B109.4
C13—C12—C11111.1 (3)C26—C27—H27B109.4
C13—C12—H12A109.4H27A—C27—H27B108.0
C11—C12—H12A109.4C27—C28—C29110.9 (2)
C13—C12—H12B109.4C27—C28—H28A109.5
C11—C12—H12B109.4C29—C28—H28A109.5
H12A—C12—H12B108.0C27—C28—H28B109.5
C14—C13—C12110.5 (2)C29—C28—H28B109.5
C14—C13—H13A109.6H28A—C28—H28B108.0
C12—C13—H13A109.6C28—C29—C30111.3 (2)
C14—C13—H13B109.6C28—C29—H29A109.4
C12—C13—H13B109.6C30—C29—H29A109.4
H13A—C13—H13B108.1C28—C29—H29B109.4
C13—C14—C15111.4 (2)C30—C29—H29B109.4
C13—C14—H14A109.4H29A—C29—H29B108.0
C15—C14—H14A109.4C25—C30—C29110.5 (2)
C13—C14—H14B109.4C25—C30—H30A109.6
C15—C14—H14B109.4C29—C30—H30A109.6
H14A—C14—H14B108.0C25—C30—H30B109.6
C14—C15—C10109.8 (2)C29—C30—H30B109.6
C14—C15—H15A109.7H30A—C30—H30B108.1
O2—S1—C1—C8144.0 (2)O4—S2—C16—C23152.5 (2)
C10—S1—C1—C8105.3 (2)C25—S2—C16—C2395.1 (2)
O2—S1—C1—C235.5 (2)O4—S2—C16—C1725.0 (2)
C10—S1—C1—C275.1 (2)C25—S2—C16—C1787.4 (2)
C8—C1—C2—C3177.8 (2)C23—C16—C17—C18177.1 (3)
S1—C1—C2—C32.5 (4)S2—C16—C17—C180.7 (4)
C8—C1—C2—C70.7 (2)C23—C16—C17—C221.5 (2)
S1—C1—C2—C7178.90 (17)S2—C16—C17—C22179.34 (18)
C7—C2—C3—C40.2 (3)C22—C17—C18—C190.5 (3)
C1—C2—C3—C4178.6 (2)C16—C17—C18—C19179.0 (2)
C2—C3—C4—C50.5 (3)C17—C18—C19—C200.9 (4)
C2—C3—C4—Br1179.47 (16)C17—C18—C19—Br2177.68 (16)
C3—C4—C5—C60.0 (4)C18—C19—C20—C211.4 (4)
Br1—C4—C5—C6179.90 (18)Br2—C19—C20—C21177.15 (19)
C4—C5—C6—C71.0 (3)C19—C20—C21—C220.5 (4)
C8—O1—C7—C6179.9 (2)C23—O3—C22—C21179.3 (2)
C8—O1—C7—C20.7 (2)C23—O3—C22—C170.4 (3)
C5—C6—C7—O1177.4 (2)C20—C21—C22—O3178.7 (2)
C5—C6—C7—C21.6 (4)C20—C21—C22—C170.9 (4)
C3—C2—C7—O1177.94 (19)C18—C17—C22—O3178.2 (2)
C1—C2—C7—O10.9 (2)C16—C17—C22—O30.7 (2)
C3—C2—C7—C61.3 (4)C18—C17—C22—C211.4 (4)
C1—C2—C7—C6179.9 (2)C16—C17—C22—C21179.6 (2)
C2—C1—C8—O10.3 (3)C17—C16—C23—O31.9 (3)
S1—C1—C8—O1179.31 (15)S2—C16—C23—O3179.85 (15)
C2—C1—C8—C9175.8 (2)C17—C16—C23—C24178.5 (2)
S1—C1—C8—C94.5 (4)S2—C16—C23—C240.5 (4)
C7—O1—C8—C10.2 (2)C22—O3—C23—C161.4 (3)
C7—O1—C8—C9177.06 (19)C22—O3—C23—C24178.9 (2)
O2—S1—C10—C11179.02 (18)O4—S2—C25—C3048.50 (19)
C1—S1—C10—C1168.28 (19)C16—S2—C25—C3063.80 (19)
O2—S1—C10—C1558.37 (19)O4—S2—C25—C2675.73 (18)
C1—S1—C10—C15169.11 (17)C16—S2—C25—C26171.97 (17)
C15—C10—C11—C1254.9 (3)C30—C25—C26—C2756.7 (3)
S1—C10—C11—C12175.7 (2)S2—C25—C26—C27177.98 (17)
C10—C11—C12—C1354.7 (4)C25—C26—C27—C2857.1 (3)
C11—C12—C13—C1456.2 (4)C26—C27—C28—C2957.3 (3)
C12—C13—C14—C1558.1 (3)C27—C28—C29—C3056.1 (3)
C13—C14—C15—C1057.5 (3)C26—C25—C30—C2955.7 (3)
C11—C10—C15—C1456.0 (3)S2—C25—C30—C29177.52 (16)
S1—C10—C15—C14177.3 (2)C28—C29—C30—C2555.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.952.563.495 (3)170
C25—H25···O21.002.573.409 (3)142
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H17BrO2S
Mr341.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)12.1842 (2), 9.0281 (1), 26.6191 (4)
β (°) 97.702 (1)
V3)2901.69 (7)
Z8
Radiation typeMo Kα
µ (mm1)2.97
Crystal size (mm)0.31 × 0.22 × 0.18
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.579, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
26831, 6674, 4944
Rint0.041
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.088, 1.04
No. of reflections6674
No. of parameters345
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.56

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···O2i0.952.563.495 (3)170
C25—H25···O21.002.573.409 (3)142
Symmetry code: (i) x, y+1, z.
 

References

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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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