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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 9| September 2014| Pages o1067-o1068
doi:10.1107/S1600536814019217

Crystal structure of 5-chloro-3-cyclo­hexyl­sulfinyl-2,4,6-tri­methyl-1-benzo­furan

Hong Dae Choia and Uk Leeb*

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 August 2014; accepted 26 August 2014; online 30 August 2014)

In the title compound, C17H21ClO2S, the cyclo­hexyl ring adopts a chair conformation with the C—S bond in an equatorial orientation. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯π hydrogen bonds and a Cl⋯π [3.594 (2) Å] contact into chains along the a-axis direction.

CCDC reference: 1021106

1. Related literature

For the biological 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.]); Howlett et al. (1999[Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]); Ono et al. (2002[Ono, M., Kung, M. P., Hou, C. & Kung, H. F. (2002). Nucl. Med. Biol. 29, 633-642.]). For natural products with a benzo­furan ring, 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 synthesis of the starting material 5-chloro-3-cyclo­hexyl­sulfanyl-2,4,6-trimethyl-1-benzo­furan, see: Choi et al. (1999[Choi, H. D., Seo, P. J. & Son, B. W. (1999). J. Korean Chem. Soc. 43, 606-608.]). For a related structure, see: Choi et al. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o804.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H21ClO2S

  • Mr = 324.85

  • Triclinic, [P \overline 1]

  • a = 5.8612 (1) Å

  • b = 11.6832 (2) Å

  • c = 12.6432 (2) Å

  • α = 65.292 (1)°

  • β = 85.902 (1)°

  • γ = 83.229 (1)°

  • V = 780.79 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.38 mm−1

  • T = 173 K

  • 0.31 × 0.24 × 0.23 mm

2.2. 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 = 0.892, Tmax = 0.917

  • 13925 measured reflections

  • 3588 independent reflections

  • 3221 reflections with I > 2σ(I)

  • Rint = 0.024

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.102

  • S = 1.03

  • 3588 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C9—H9A⋯O2i 0.98 2.53 3.438 (2) 154
C12—H12⋯O2i 1.00 2.39 3.3072 (19) 152
C11—H11b⋯Cg2i 0.98 2.83 3.533 (2) 129
Symmetry code: (i) x-1, y, 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1021106

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814019217/hb7277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019217/hb7277Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814019217/hb7277Isup3.cml

checkCIF report


Comment top

Benzofuran compounds show significant pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009, Galal et al., 2009, Khan et al. , 2005), and inhibitor of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These many benzofurans occur in a great number of natural products (Akgul & Anil, 2003, Soekamto et al., 2003). As a part of our ongoing project of 5-chloro-3-cyclohexylsulfinyl-1-benzofuran derivatives containing methyl substituent in 2-position (Choi et al., 2011), 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 0.014 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form and the arylsulfinyl moiety is positioned equatorially relative to the cyclohexyl group. In the crystal structure (Fig. 2), molecules are linked by C—H···O and C—H···π hydrogen bonds (Table 1, Cg2 is the centroid of the C2–C7 benzene ring). The molecules are stacked along the a-axis. A Cl···π contact between the chlorine atom and the furan ring of an adjacent molecule, with Cl1···Cg1i [3.594 (2) Å] (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring) is observed, compared to the van der Waals' separation of 3.55Å for these species.

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Khan et al. (2005); Ono et al. (2002). For natural products with a benzofuran ring, see: Akgul & Anil (2003); Soekamto et al. (2003). For the synthesis of the starting material 5-chloro-3-cyclohexylsulfanyl-2,4,6-trimethyl-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2011).

Experimental top

The starting material 5-chloro-3-cyclohexylsulfanyl-2,4,6-trimethyl-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclohexylsulfanyl-2,4,6-trimethyl-1-benzofuran (278 mg, 0.9 mmol) in dichloromethane (20 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution (2 × 10 ml) 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 77% (250 mg); m.p. 449–450 K; Rf = 0.61 (hexane–ethyl acetate, 2:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound (26 mg) in ethyl acetate (10 ml) 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 Åfor methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso = 1.2Ueq (C) for aryl, methine and methylene, and 1.5Ueq for methyl H atoms. The positions of methyl and methylene hydrogens were optimized using the SHELXL-97 command AFIX 137 (Sheldrick, 2008).

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 for Windows (Farrugia, 2012) 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.
[Figure 2] Fig. 2. A view of the C—H···O, C—H···π and C—Cl···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z.]
5-Chloro-3-cyclohexylsulfinyl-2,4,6-trimethyl-1-benzofuran top
Crystal data top
C17H21ClO2SZ = 2
Mr = 324.85F(000) = 344
Triclinic, P1Dx = 1.382 Mg m−3
Hall symbol: -P 1Melting point = 417–416 K
a = 5.8612 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6832 (2) ÅCell parameters from 5736 reflections
c = 12.6432 (2) Åθ = 3.1–27.5°
α = 65.292 (1)°µ = 0.38 mm−1
β = 85.902 (1)°T = 173 K
γ = 83.229 (1)°Block, colourless
V = 780.79 (2) Å30.31 × 0.24 × 0.23 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3588 independent reflections
Radiation source: rotating anode3221 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.024
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.8°
ϕ and ω scansh = −7→6
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −15→15
Tmin = 0.892, Tmax = 0.917l = −16→16
13925 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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.102H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0521P)2 + 0.403P]
where P = (Fo2 + 2Fc2)/3
3588 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.77 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C17H21ClO2Sγ = 83.229 (1)°
Mr = 324.85V = 780.79 (2) Å3
Triclinic, P1Z = 2
a = 5.8612 (1) ÅMo Kα radiation
b = 11.6832 (2) ŵ = 0.38 mm−1
c = 12.6432 (2) ÅT = 173 K
α = 65.292 (1)°0.31 × 0.24 × 0.23 mm
β = 85.902 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3588 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3221 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.917Rint = 0.024
13925 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.03Δρmax = 0.77 e Å−3
3588 reflectionsΔρmin = −0.37 e Å−3
193 parameters
Special details top

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 7.19 (s, 1H), 2.73 (s, 3H), 2.36 (s, 3H), 2.31 (s, 3H), 1.63-2.12 (m, 5H), 1.10-1.58 (m, 6H).

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
Cl1−0.27225 (7)0.86676 (4)0.02495 (4)0.03675 (13)
S10.57459 (7)0.47693 (4)0.17641 (4)0.02576 (12)
O10.47568 (19)0.69596 (10)0.34877 (10)0.0266 (2)
O20.8052 (2)0.41466 (12)0.22085 (12)0.0382 (3)
C10.4841 (3)0.58674 (14)0.23789 (13)0.0218 (3)
C20.2864 (2)0.68140 (14)0.20410 (13)0.0213 (3)
C30.1136 (3)0.71923 (14)0.12166 (13)0.0225 (3)
C4−0.0488 (3)0.81617 (15)0.12320 (14)0.0257 (3)
C5−0.0466 (3)0.87677 (14)0.19854 (15)0.0282 (3)
C60.1294 (3)0.83926 (15)0.27712 (15)0.0277 (3)
H60.13880.87830.32900.033*
C70.2904 (3)0.74323 (14)0.27712 (13)0.0238 (3)
C80.5900 (3)0.60035 (14)0.32321 (14)0.0243 (3)
C90.1048 (3)0.66135 (16)0.03624 (14)0.0283 (3)
H9A−0.00590.59770.06450.042*
H9B0.25740.62110.02790.042*
H9C0.05720.7275−0.03950.042*
C10−0.2283 (3)0.98104 (17)0.19422 (18)0.0377 (4)
H10A−0.19571.01250.25170.056*
H10B−0.37920.94810.21190.056*
H10C−0.22811.05030.11620.056*
C110.7959 (3)0.53609 (17)0.39374 (15)0.0318 (4)
H11A0.74810.48580.47440.048*
H11B0.89330.59960.39190.048*
H11C0.88260.48030.36160.048*
C120.3682 (3)0.36179 (14)0.25301 (13)0.0220 (3)
H120.21010.40710.24060.026*
C160.2432 (4)0.19538 (17)0.44265 (15)0.0383 (4)
H16A0.27760.15070.52650.046*
H16B0.08370.23610.43570.046*
C170.4088 (3)0.29673 (16)0.38293 (14)0.0318 (4)
H17A0.38610.36010.41660.038*
H17B0.56910.25730.39660.038*
C130.3866 (3)0.26742 (15)0.19771 (14)0.0274 (3)
H13A0.35000.31250.11420.033*
H13B0.54590.22670.20360.033*
C140.2215 (3)0.16667 (16)0.25851 (15)0.0325 (4)
H14A0.06140.20660.24580.039*
H14B0.24150.10370.22430.039*
C150.2635 (4)0.10016 (16)0.38823 (16)0.0382 (4)
H15A0.41900.05390.40130.046*
H15B0.15000.03780.42600.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0255 (2)0.0385 (2)0.0353 (2)0.00422 (17)−0.00709 (17)−0.00539 (18)
S10.0211 (2)0.0256 (2)0.0315 (2)−0.00217 (14)0.00493 (15)−0.01365 (16)
O10.0263 (6)0.0269 (6)0.0297 (6)−0.0042 (4)−0.0037 (5)−0.0137 (5)
O20.0201 (6)0.0393 (7)0.0566 (8)0.0026 (5)0.0011 (5)−0.0231 (6)
C10.0180 (7)0.0213 (7)0.0255 (7)−0.0026 (5)0.0000 (5)−0.0088 (6)
C20.0181 (7)0.0201 (7)0.0245 (7)−0.0038 (5)0.0022 (6)−0.0078 (6)
C30.0203 (7)0.0218 (7)0.0225 (7)−0.0044 (6)0.0019 (6)−0.0060 (6)
C40.0195 (7)0.0243 (7)0.0259 (8)−0.0019 (6)−0.0001 (6)−0.0033 (6)
C50.0256 (8)0.0198 (7)0.0330 (8)−0.0020 (6)0.0059 (6)−0.0057 (6)
C60.0308 (8)0.0225 (7)0.0319 (8)−0.0057 (6)0.0049 (7)−0.0133 (6)
C70.0227 (7)0.0226 (7)0.0258 (7)−0.0049 (6)0.0002 (6)−0.0092 (6)
C80.0209 (7)0.0231 (7)0.0283 (8)−0.0044 (6)0.0001 (6)−0.0096 (6)
C90.0266 (8)0.0322 (8)0.0259 (8)−0.0018 (6)−0.0032 (6)−0.0116 (7)
C100.0320 (9)0.0264 (8)0.0490 (11)0.0030 (7)0.0068 (8)−0.0128 (8)
C110.0247 (8)0.0352 (9)0.0323 (9)−0.0022 (7)−0.0074 (7)−0.0100 (7)
C120.0192 (7)0.0222 (7)0.0247 (7)−0.0009 (5)0.0002 (5)−0.0102 (6)
C160.0529 (12)0.0331 (9)0.0266 (9)−0.0095 (8)0.0087 (8)−0.0101 (7)
C170.0410 (10)0.0318 (9)0.0244 (8)−0.0058 (7)−0.0009 (7)−0.0128 (7)
C130.0326 (9)0.0262 (8)0.0256 (8)−0.0027 (6)0.0008 (6)−0.0130 (6)
C140.0376 (9)0.0267 (8)0.0358 (9)−0.0067 (7)0.0010 (7)−0.0150 (7)
C150.0514 (12)0.0244 (8)0.0347 (9)−0.0078 (8)0.0070 (8)−0.0084 (7)
Geometric parameters (Å, º) top
Cl1—C41.7444 (16)C10—H10B0.9800
S1—O21.4857 (12)C10—H10C0.9800
S1—C11.7737 (16)C11—H11A0.9800
S1—C121.8268 (16)C11—H11B0.9800
O1—C71.3734 (19)C11—H11C0.9800
O1—C81.3768 (19)C12—C171.517 (2)
C1—C81.355 (2)C12—C131.524 (2)
C1—C21.456 (2)C12—H121.0000
C2—C71.392 (2)C16—C151.524 (3)
C2—C31.403 (2)C16—C171.527 (3)
C3—C41.397 (2)C16—H16A0.9900
C3—C91.501 (2)C16—H16B0.9900
C4—C51.406 (2)C17—H17A0.9900
C5—C61.385 (2)C17—H17B0.9900
C5—C101.506 (2)C13—C141.523 (2)
C6—C71.378 (2)C13—H13A0.9900
C6—H60.9500C13—H13B0.9900
C8—C111.482 (2)C14—C151.517 (2)
C9—H9A0.9800C14—H14A0.9900
C9—H9B0.9800C14—H14B0.9900
C9—H9C0.9800C15—H15A0.9900
C10—H10A0.9800C15—H15B0.9900
O2—S1—C1108.70 (7)C8—C11—H11B109.5
O2—S1—C12106.89 (7)H11A—C11—H11B109.5
C1—S1—C1298.02 (7)C8—C11—H11C109.5
C7—O1—C8106.43 (12)H11A—C11—H11C109.5
C8—C1—C2107.18 (13)H11B—C11—H11C109.5
C8—C1—S1126.24 (12)C17—C12—C13111.82 (13)
C2—C1—S1126.56 (12)C17—C12—S1112.03 (11)
C7—C2—C3119.57 (14)C13—C12—S1107.37 (10)
C7—C2—C1104.35 (13)C17—C12—H12108.5
C3—C2—C1136.08 (14)C13—C12—H12108.5
C4—C3—C2115.37 (14)S1—C12—H12108.5
C4—C3—C9122.03 (14)C15—C16—C17111.07 (15)
C2—C3—C9122.59 (14)C15—C16—H16A109.4
C3—C4—C5124.84 (15)C17—C16—H16A109.4
C3—C4—Cl1118.17 (13)C15—C16—H16B109.4
C5—C4—Cl1116.99 (12)C17—C16—H16B109.4
C6—C5—C4118.38 (14)H16A—C16—H16B108.0
C6—C5—C10120.13 (16)C12—C17—C16110.44 (14)
C4—C5—C10121.48 (16)C12—C17—H17A109.6
C7—C6—C5117.47 (15)C16—C17—H17A109.6
C7—C6—H6121.3C12—C17—H17B109.6
C5—C6—H6121.3C16—C17—H17B109.6
O1—C7—C6124.62 (15)H17A—C17—H17B108.1
O1—C7—C2111.05 (13)C14—C13—C12110.48 (13)
C6—C7—C2124.33 (15)C14—C13—H13A109.6
C1—C8—O1110.96 (13)C12—C13—H13A109.6
C1—C8—C11134.70 (15)C14—C13—H13B109.6
O1—C8—C11114.33 (14)C12—C13—H13B109.6
C3—C9—H9A109.5H13A—C13—H13B108.1
C3—C9—H9B109.5C15—C14—C13111.19 (15)
H9A—C9—H9B109.5C15—C14—H14A109.4
C3—C9—H9C109.5C13—C14—H14A109.4
H9A—C9—H9C109.5C15—C14—H14B109.4
H9B—C9—H9C109.5C13—C14—H14B109.4
C5—C10—H10A109.5H14A—C14—H14B108.0
C5—C10—H10B109.5C14—C15—C16110.65 (14)
H10A—C10—H10B109.5C14—C15—H15A109.5
C5—C10—H10C109.5C16—C15—H15A109.5
H10A—C10—H10C109.5C14—C15—H15B109.5
H10B—C10—H10C109.5C16—C15—H15B109.5
C8—C11—H11A109.5H15A—C15—H15B108.1
O2—S1—C1—C8−8.41 (17)C5—C6—C7—O1179.49 (14)
C12—S1—C1—C8102.54 (15)C5—C6—C7—C2−0.4 (2)
O2—S1—C1—C2169.73 (13)C3—C2—C7—O1−177.97 (13)
C12—S1—C1—C2−79.33 (14)C1—C2—C7—O11.59 (17)
C8—C1—C2—C7−1.28 (17)C3—C2—C7—C62.0 (2)
S1—C1—C2—C7−179.71 (11)C1—C2—C7—C6−178.49 (15)
C8—C1—C2—C3178.16 (17)C2—C1—C8—O10.56 (17)
S1—C1—C2—C3−0.3 (3)S1—C1—C8—O1178.99 (11)
C7—C2—C3—C4−2.1 (2)C2—C1—C8—C11−179.83 (17)
C1—C2—C3—C4178.50 (16)S1—C1—C8—C11−1.4 (3)
C7—C2—C3—C9176.98 (14)C7—O1—C8—C10.42 (17)
C1—C2—C3—C9−2.4 (3)C7—O1—C8—C11−179.28 (13)
C2—C3—C4—C51.0 (2)O2—S1—C12—C1745.90 (13)
C9—C3—C4—C5−178.09 (15)C1—S1—C12—C17−66.51 (12)
C2—C3—C4—Cl1−178.93 (11)O2—S1—C12—C13−77.25 (12)
C9—C3—C4—Cl12.0 (2)C1—S1—C12—C13170.35 (11)
C3—C4—C5—C60.4 (2)C13—C12—C17—C16−55.75 (19)
Cl1—C4—C5—C6−179.62 (12)S1—C12—C17—C16−176.35 (12)
C3—C4—C5—C10179.79 (15)C15—C16—C17—C1256.0 (2)
Cl1—C4—C5—C10−0.3 (2)C17—C12—C13—C1455.82 (18)
C4—C5—C6—C7−0.7 (2)S1—C12—C13—C14179.10 (11)
C10—C5—C6—C7179.89 (15)C12—C13—C14—C15−56.10 (19)
C8—O1—C7—C6178.78 (15)C13—C14—C15—C1656.9 (2)
C8—O1—C7—C2−1.29 (17)C17—C16—C15—C14−56.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2i0.982.533.438 (2)154
C12—H12···O2i1.002.393.3072 (19)152
C11—H11b···Cg2i0.982.833.533 (2)129
Symmetry code: (i) x−1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2i0.982.533.438 (2)154
C12—H12···O2i1.002.393.3072 (19)152
C11—H11b···Cg2i0.982.833.533 (2)129
Symmetry code: (i) x−1, y, z.
 

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

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ISSN: 2056-9890
Volume 70| Part 9| September 2014| Pages o1067-o1068
doi:10.1107/S1600536814019217
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