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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 12| December 2014| Pages o1233-o1234

Crystal structure of 5-chloro-2,4,6-tri­methyl-3-(4-methyl­phenyl­sulfin­yl)-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

Edited by G. S. Nichol, University of Edinburgh, Scotland (Received 19 August 2014; accepted 29 October 2014; online 5 November 2014)

In the title compound, C18H17ClO2S, the dihedral angle between the planes of the benzo­furan ring [r.m.s. deviation = 0.013 (1) Å] and the 4-methyl­phenyl ring is 87.37 (5)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and ππ inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.525 (2) Å]. In addition, an S⋯S [3.6584 (9) Å] contact is observed.

1. Related literature

For the pharmacological properties 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.]); Wahab Khan et al. (2005[Wahab Khan, M., Jahangir Alam, M., 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-2,4,6-trimethyl-3-(4-methyl­phenyl­sulfan­yl)-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. (2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o2080.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C18H17ClO2S

  • Mr = 332.83

  • Triclinic, [P \overline 1]

  • a = 8.7938 (2) Å

  • b = 9.1775 (3) Å

  • c = 10.7298 (3) Å

  • α = 86.571 (1)°

  • β = 69.157 (1)°

  • γ = 81.093 (2)°

  • V = 799.51 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 173 K

  • 0.60 × 0.56 × 0.08 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 = 0.807, Tmax = 0.971

  • 14763 measured reflections

  • 3988 independent reflections

  • 3502 reflections with I > 2σ(I)

  • Rint = 0.048

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.124

  • S = 1.05

  • 3988 reflections

  • 203 parameters

  • H-atom parameters constrained

  • Δρmax = 0.83 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O2i 0.95 2.30 3.180 (2) 154
C17—H17⋯O1ii 0.95 2.56 3.434 (2) 153
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+1.

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


Comment top

Substituted benzofurans show interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009, Galal et al., 2009, Wahab Khan et al., 2005), and potential inhibitor of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These benzofuran compounds occur in a great number of natural products. (Akgul & Anil, 2003, Soekamto et al., 2003). As a part of our ongoing project of 3-arylsulfinyl-5-chloro-2-methyl-1-benzofuran derivatives containing 4-bromophenylsulfinyl substituent in 3-position (Choi et al., 2012), 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 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.003 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 4-methylphenyl ring is 87.37 (5)°. In the crystal structure (Fig. 2), molecules are linked by C—H···O hydrogen bonds (Table 1) and ππ interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2iii distance of 3.525 (2) Å and an interplanar distance of 3.479 (2) Å resulting in a slippage of 0.568 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively). In the crystal (Fig. 2), an S1···S1iv [3.6584 (9) Å] contact are observed.

Related literature top

For the pharmacological properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Wahab 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-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2012).

Experimental top

The starting material 5-chloro-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-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-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (285 mg, 0.9 mmol) in dichloromethane (25 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X 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 68% (226 mg); m.p. 466–467 K; Rf = 0.43 (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 (23 mg) in acetone (15 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 and 0.98 Å for methyl H atoms, Uiso (H) = 1.2Ueq (C) for aryl and 1.5Ueq (C) for methyl H atoms.The positions of methyl hydrogens were optimized using the SHELXL-97's 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
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 small spheres of arbitrary radius.

Fig. 2. A view of the C—H···O, ππ and S···S 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 + 2, - z + 1; (iii) - x + 1, - y + 1, - z + 1; (iv) - x, - y + 2, - z + 1; (v) x - 1, y, z; (vi) x, y - 1, z.]
5-Chloro-2,4,6-trimethyl-3-(4-methylphenylsulfinyl)-1-benzofuran top
Crystal data top
C18H17ClO2SZ = 2
Mr = 332.83F(000) = 348
Triclinic, P1Dx = 1.383 Mg m3
Hall symbol: -P 1Melting point = 467–466 K
a = 8.7938 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1775 (3) ÅCell parameters from 6565 reflections
c = 10.7298 (3) Åθ = 2.6–28.3°
α = 86.571 (1)°µ = 0.37 mm1
β = 69.157 (1)°T = 173 K
γ = 81.093 (2)°Block, colourless
V = 799.51 (4) Å30.60 × 0.56 × 0.08 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3988 independent reflections
Radiation source: rotating anode3502 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.048
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.0°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1212
Tmin = 0.807, Tmax = 0.971l = 1114
14763 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)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.124H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2785P]
where P = (Fo2 + 2Fc2)/3
3988 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.83 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
C18H17ClO2Sγ = 81.093 (2)°
Mr = 332.83V = 799.51 (4) Å3
Triclinic, P1Z = 2
a = 8.7938 (2) ÅMo Kα radiation
b = 9.1775 (3) ŵ = 0.37 mm1
c = 10.7298 (3) ÅT = 173 K
α = 86.571 (1)°0.60 × 0.56 × 0.08 mm
β = 69.157 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3988 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3502 reflections with I > 2σ(I)
Tmin = 0.807, Tmax = 0.971Rint = 0.048
14763 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.05Δρmax = 0.83 e Å3
3988 reflectionsΔρmin = 0.41 e Å3
203 parameters
Special details top

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 7.34 (d, J = 8.24 Hz, 2H), 7.22 (d, J = 7.84 Hz, 2H), 7.19 (s, 1H), 2.71 (s, 3H), 2.43 (s, 3H), 2.37 (s, 3H), 2.32 (s, 3H).

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
Cl10.73398 (7)0.38071 (5)0.09920 (5)0.04987 (16)
S10.14021 (5)0.82594 (5)0.46437 (4)0.03532 (13)
O10.54038 (13)0.77389 (12)0.54951 (11)0.0305 (2)
O20.06142 (17)0.69774 (17)0.45239 (15)0.0502 (4)
C10.33771 (18)0.76626 (16)0.46945 (16)0.0281 (3)
C20.47994 (18)0.66515 (15)0.39027 (15)0.0256 (3)
C30.5174 (2)0.56896 (16)0.28374 (16)0.0298 (3)
C40.6780 (2)0.49579 (17)0.23736 (16)0.0321 (3)
C50.7994 (2)0.50928 (18)0.29109 (17)0.0330 (3)
C60.75771 (19)0.60170 (17)0.39906 (16)0.0315 (3)
H60.83450.61310.44030.038*
C70.60010 (19)0.67636 (16)0.44414 (15)0.0265 (3)
C80.38130 (19)0.82609 (17)0.56227 (16)0.0296 (3)
C90.3921 (3)0.5445 (2)0.2249 (2)0.0471 (5)
H9A0.41140.59900.14060.071*
H9B0.28170.57940.28720.071*
H9C0.40150.43900.20840.071*
C100.9703 (2)0.4263 (2)0.2351 (2)0.0486 (5)
H10A1.03220.44160.29210.073*
H10B1.02560.46230.14490.073*
H10C0.96450.32090.23200.073*
C110.2955 (2)0.9357 (2)0.66964 (18)0.0405 (4)
H11A0.33791.02970.64270.061*
H11B0.31450.90000.75150.061*
H11C0.17730.94990.68570.061*
C120.19683 (19)0.91671 (17)0.30487 (16)0.0303 (3)
C130.1421 (2)0.87745 (19)0.20800 (19)0.0374 (4)
H130.08400.79540.22110.045*
C140.1729 (2)0.9595 (2)0.09110 (19)0.0426 (4)
H140.13590.93240.02380.051*
C150.2563 (3)1.07992 (19)0.07025 (18)0.0433 (4)
C160.3090 (3)1.11627 (19)0.1702 (2)0.0448 (4)
H160.36711.19820.15760.054*
C170.2795 (2)1.03701 (19)0.28696 (19)0.0383 (4)
H170.31551.06450.35470.046*
C180.2873 (4)1.1712 (2)0.0548 (2)0.0668 (7)
H18A0.40041.14250.11530.100*
H18B0.27111.27580.03230.100*
H18C0.21051.15500.09830.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0693 (3)0.0399 (2)0.0368 (2)0.0026 (2)0.0170 (2)0.01002 (18)
S10.0252 (2)0.0470 (3)0.0337 (2)0.00534 (16)0.01096 (16)0.00375 (17)
O10.0335 (6)0.0326 (5)0.0308 (6)0.0075 (4)0.0165 (5)0.0015 (4)
O20.0404 (7)0.0647 (9)0.0563 (9)0.0267 (6)0.0252 (7)0.0181 (7)
C10.0271 (7)0.0302 (7)0.0285 (7)0.0066 (6)0.0109 (6)0.0033 (6)
C20.0271 (7)0.0255 (6)0.0278 (7)0.0082 (5)0.0129 (6)0.0045 (5)
C30.0373 (8)0.0276 (7)0.0295 (8)0.0077 (6)0.0168 (7)0.0012 (6)
C40.0420 (9)0.0266 (7)0.0274 (7)0.0058 (6)0.0116 (7)0.0016 (6)
C50.0314 (8)0.0323 (8)0.0312 (8)0.0045 (6)0.0072 (6)0.0067 (6)
C60.0292 (7)0.0346 (8)0.0342 (8)0.0089 (6)0.0146 (6)0.0059 (6)
C70.0298 (7)0.0264 (7)0.0265 (7)0.0085 (5)0.0123 (6)0.0024 (5)
C80.0309 (7)0.0297 (7)0.0293 (8)0.0062 (6)0.0117 (6)0.0031 (6)
C90.0541 (11)0.0450 (10)0.0563 (12)0.0038 (8)0.0359 (10)0.0133 (9)
C100.0346 (9)0.0530 (11)0.0465 (11)0.0025 (8)0.0043 (8)0.0032 (9)
C110.0484 (10)0.0385 (9)0.0327 (9)0.0041 (7)0.0122 (8)0.0044 (7)
C120.0262 (7)0.0323 (7)0.0310 (8)0.0008 (6)0.0103 (6)0.0003 (6)
C130.0385 (9)0.0350 (8)0.0419 (9)0.0027 (7)0.0190 (8)0.0017 (7)
C140.0548 (11)0.0390 (9)0.0354 (9)0.0051 (8)0.0216 (8)0.0067 (7)
C150.0565 (11)0.0307 (8)0.0335 (9)0.0074 (7)0.0097 (8)0.0024 (7)
C160.0544 (11)0.0300 (8)0.0477 (11)0.0071 (8)0.0149 (9)0.0007 (7)
C170.0429 (9)0.0356 (8)0.0399 (9)0.0045 (7)0.0190 (8)0.0032 (7)
C180.105 (2)0.0425 (11)0.0395 (11)0.0014 (12)0.0150 (12)0.0042 (9)
Geometric parameters (Å, º) top
Cl1—C41.7500 (16)C9—H9C0.9800
S1—O21.4882 (14)C10—H10A0.9800
S1—C11.7574 (15)C10—H10B0.9800
S1—C121.7950 (17)C10—H10C0.9800
S1—S1i3.6584 (9)C11—H11A0.9800
O1—C81.3672 (19)C11—H11B0.9800
O1—C71.3813 (18)C11—H11C0.9800
C1—C81.357 (2)C12—C131.377 (2)
C1—C21.458 (2)C12—C171.381 (2)
C2—C71.392 (2)C13—C141.386 (3)
C2—C31.399 (2)C13—H130.9500
C3—C41.393 (2)C14—C151.384 (3)
C3—C91.501 (2)C14—H140.9500
C4—C51.405 (2)C15—C161.386 (3)
C5—C61.384 (2)C15—C181.501 (3)
C5—C101.502 (2)C16—C171.372 (3)
C6—C71.376 (2)C16—H160.9500
C6—H60.9500C17—H170.9500
C8—C111.481 (2)C18—H18A0.9800
C9—H9A0.9800C18—H18B0.9800
C9—H9B0.9800C18—H18C0.9800
O2—S1—C1110.50 (8)C5—C10—H10A109.5
O2—S1—C12106.80 (8)C5—C10—H10B109.5
C1—S1—C1298.98 (7)H10A—C10—H10B109.5
O2—S1—S1i113.79 (6)C5—C10—H10C109.5
C1—S1—S1i134.58 (5)H10A—C10—H10C109.5
C12—S1—S1i77.68 (5)H10B—C10—H10C109.5
C8—O1—C7106.51 (11)C8—C11—H11A109.5
C8—C1—C2107.06 (13)C8—C11—H11B109.5
C8—C1—S1118.18 (12)H11A—C11—H11B109.5
C2—C1—S1134.71 (12)C8—C11—H11C109.5
C7—C2—C3118.93 (14)H11A—C11—H11C109.5
C7—C2—C1104.37 (13)H11B—C11—H11C109.5
C3—C2—C1136.70 (14)C13—C12—C17120.71 (16)
C4—C3—C2115.52 (14)C13—C12—S1120.19 (13)
C4—C3—C9122.27 (15)C17—C12—S1118.68 (13)
C2—C3—C9122.20 (15)C12—C13—C14119.00 (17)
C3—C4—C5125.18 (15)C12—C13—H13120.5
C3—C4—Cl1117.32 (12)C14—C13—H13120.5
C5—C4—Cl1117.49 (13)C15—C14—C13121.47 (17)
C6—C5—C4118.13 (15)C15—C14—H14119.3
C6—C5—C10119.95 (16)C13—C14—H14119.3
C4—C5—C10121.92 (17)C14—C15—C16117.83 (17)
C7—C6—C5117.09 (14)C14—C15—C18121.9 (2)
C7—C6—H6121.5C16—C15—C18120.3 (2)
C5—C6—H6121.5C17—C16—C15121.75 (18)
C6—C7—O1124.07 (13)C17—C16—H16119.1
C6—C7—C2125.10 (14)C15—C16—H16119.1
O1—C7—C2110.83 (13)C16—C17—C12119.23 (16)
C1—C8—O1111.21 (13)C16—C17—H17120.4
C1—C8—C11133.88 (15)C12—C17—H17120.4
O1—C8—C11114.89 (14)C15—C18—H18A109.5
C3—C9—H9A109.5C15—C18—H18B109.5
C3—C9—H9B109.5H18A—C18—H18B109.5
H9A—C9—H9B109.5C15—C18—H18C109.5
C3—C9—H9C109.5H18A—C18—H18C109.5
H9A—C9—H9C109.5H18B—C18—H18C109.5
H9B—C9—H9C109.5
O2—S1—C1—C8134.63 (14)C8—O1—C7—C20.45 (16)
C12—S1—C1—C8113.57 (14)C3—C2—C7—C61.5 (2)
S1i—S1—C1—C832.06 (17)C1—C2—C7—C6178.85 (15)
O2—S1—C1—C248.36 (18)C3—C2—C7—O1178.86 (13)
C12—S1—C1—C263.44 (17)C1—C2—C7—O10.82 (16)
S1i—S1—C1—C2144.96 (13)C2—C1—C8—O10.66 (18)
C8—C1—C2—C70.88 (17)S1—C1—C8—O1177.12 (10)
S1—C1—C2—C7176.36 (13)C2—C1—C8—C11179.10 (17)
C8—C1—C2—C3178.70 (17)S1—C1—C8—C111.3 (3)
S1—C1—C2—C34.1 (3)C7—O1—C8—C10.16 (17)
C7—C2—C3—C42.4 (2)C7—O1—C8—C11178.91 (13)
C1—C2—C3—C4178.08 (16)O2—S1—C12—C1310.13 (16)
C7—C2—C3—C9176.67 (16)C1—S1—C12—C13124.85 (14)
C1—C2—C3—C92.9 (3)S1i—S1—C12—C13101.30 (13)
C2—C3—C4—C51.6 (2)O2—S1—C12—C17177.26 (13)
C9—C3—C4—C5177.46 (17)C1—S1—C12—C1762.55 (14)
C2—C3—C4—Cl1177.10 (11)S1i—S1—C12—C1771.31 (13)
C9—C3—C4—Cl13.8 (2)C17—C12—C13—C140.8 (2)
C3—C4—C5—C60.3 (3)S1—C12—C13—C14173.25 (13)
Cl1—C4—C5—C6179.01 (12)C12—C13—C14—C150.4 (3)
C3—C4—C5—C10179.99 (16)C13—C14—C15—C160.2 (3)
Cl1—C4—C5—C101.3 (2)C13—C14—C15—C18178.73 (18)
C4—C5—C6—C71.3 (2)C14—C15—C16—C170.4 (3)
C10—C5—C6—C7178.96 (15)C18—C15—C16—C17178.56 (19)
C5—C6—C7—O1179.13 (14)C15—C16—C17—C120.8 (3)
C5—C6—C7—C20.5 (2)C13—C12—C17—C161.0 (3)
C8—O1—C7—C6179.22 (15)S1—C12—C17—C16173.55 (13)
Symmetry code: (i) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2ii0.952.303.180 (2)154
C17—H17···O1iii0.952.563.434 (2)153
Symmetry codes: (ii) x+1, y, z; (iii) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.952.303.180 (2)154.3
C17—H17···O1ii0.952.563.434 (2)153.1
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z+1.
 

Acknowledgements

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

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Volume 70| Part 12| December 2014| Pages o1233-o1234
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