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ISSN: 2056-9890

5-Chloro-2-methyl-3-(4-methyl­phenyl­sulfon­yl)-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 20 May 2013; accepted 4 June 2013; online 8 June 2013)

The title compound, C16H13ClO3S, crystallized with two independent mol­ecules in the asymmetric unit. The 4-methyl­phenyl rings make dihedral angles of 75.15 (4)° and 72.18 (4)° with the planes of the benzo­furan ring systems in the two mol­ecules. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2350.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o2027.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13ClO3S

  • Mr = 320.77

  • Triclinic, [P \overline 1]

  • a = 7.3725 (2) Å

  • b = 10.0967 (3) Å

  • c = 20.8173 (7) Å

  • α = 98.086 (1)°

  • β = 99.547 (2)°

  • γ = 106.547 (1)°

  • V = 1435.62 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.42 mm−1

  • T = 173 K

  • 0.41 × 0.29 × 0.23 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 = 0.670, Tmax = 0.746

  • 26328 measured reflections

  • 7109 independent reflections

  • 5967 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.098

  • S = 1.04

  • 7109 reflections

  • 383 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C26–C31 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15⋯O2i 0.95 2.56 3.251 (2) 130
C27—H27⋯O6ii 0.95 2.55 3.248 (2) 131
C30—H30⋯O3iii 0.95 2.48 3.361 (2) 154
C22—H22⋯Cgiv 0.95 2.71 3.572 (2) 136
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y, -z; (iii) x+1, y, z; (iv) -x+1, -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 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

As a part of our continuing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010) and 4-bromophenylsulfonyl (Choi et al., 2012) substituents in 3-postion, we report herein the crystal structure of the title compound which crystallizes with two symmetrically independent molecules, A & B, in the asymmetric unit.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.006 (1) and 0.007 (1) Å, for A and B, respectively, from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the 4-methylphenyl ring and the mean plane of the benzofuran ring system are 75.15 (4)° in molecule A and 72.18 (4)° in molecule B, respectively. In the crystal packing (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C26–C31 4-methylphenyl ring), forming a three-dimensional network.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 5-chloro-2-methyl-3-(4-methylphenylsulfanyl)-1-benzofuran (346 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 68%, m.p. 461–462 K; Rf = 0.64 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene 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 0.98Å 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 rotationally.

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 the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the C—H···O and C—H···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, - y, - z + 1; (ii) - x, - y, - z; (iii) x + 1, y, z; (iv) - x + 1, - y + 1, - z; (v) - x, - y, - z.]
5-Chloro-2-methyl-3-(4-methylphenylsulfonyl)-1-benzofuran top
Crystal data top
C16H13ClO3SZ = 4
Mr = 320.77F(000) = 664
Triclinic, P1Dx = 1.484 Mg m3
Hall symbol: -P 1Melting point = 461–462 K
a = 7.3725 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0967 (3) ÅCell parameters from 9961 reflections
c = 20.8173 (7) Åθ = 2.6–28.3°
α = 98.086 (1)°µ = 0.42 mm1
β = 99.547 (2)°T = 173 K
γ = 106.547 (1)°Block, colourless
V = 1435.62 (8) Å30.41 × 0.29 × 0.23 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
7109 independent reflections
Radiation source: rotating anode5967 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 1.0°
ϕ and ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1313
Tmin = 0.670, Tmax = 0.746l = 2727
26328 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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.6008P]
where P = (Fo2 + 2Fc2)/3
7109 reflections(Δ/σ)max = 0.001
383 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C16H13ClO3Sγ = 106.547 (1)°
Mr = 320.77V = 1435.62 (8) Å3
Triclinic, P1Z = 4
a = 7.3725 (2) ÅMo Kα radiation
b = 10.0967 (3) ŵ = 0.42 mm1
c = 20.8173 (7) ÅT = 173 K
α = 98.086 (1)°0.41 × 0.29 × 0.23 mm
β = 99.547 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
7109 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5967 reflections with I > 2σ(I)
Tmin = 0.670, Tmax = 0.746Rint = 0.028
26328 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.38 e Å3
7109 reflectionsΔρmin = 0.40 e Å3
383 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
Cl10.24968 (8)0.40295 (6)0.68981 (2)0.04342 (13)
S10.03637 (6)0.18272 (4)0.393226 (19)0.02505 (10)
O10.29244 (17)0.57988 (12)0.43797 (6)0.0290 (2)
O20.13514 (17)0.13204 (12)0.44305 (6)0.0310 (3)
O30.14612 (18)0.18003 (13)0.32903 (6)0.0347 (3)
C10.1097 (2)0.35510 (16)0.42756 (7)0.0238 (3)
C20.1844 (2)0.41316 (16)0.49781 (7)0.0228 (3)
C30.1677 (2)0.36384 (17)0.55651 (8)0.0261 (3)
H30.09310.26990.55630.031*
C40.2657 (2)0.45931 (19)0.61515 (8)0.0296 (4)
C50.3744 (2)0.59807 (19)0.61716 (8)0.0328 (4)
H50.43770.65920.65880.039*
C60.3910 (2)0.64748 (18)0.55939 (9)0.0313 (4)
H60.46390.74190.55970.038*
C70.2953 (2)0.55174 (17)0.50081 (8)0.0254 (3)
C80.1795 (2)0.45846 (17)0.39433 (8)0.0270 (3)
C90.1631 (3)0.4659 (2)0.32330 (9)0.0363 (4)
H9A0.28970.47730.31190.054*
H9B0.12030.54650.31490.054*
H9C0.06860.37880.29600.054*
C100.1255 (2)0.08739 (16)0.38118 (8)0.0253 (3)
C110.1953 (3)0.08322 (18)0.32311 (8)0.0312 (4)
H110.15600.13100.28990.037*
C120.3231 (3)0.00823 (19)0.31462 (9)0.0345 (4)
H120.37320.00640.27540.041*
C130.3796 (2)0.06433 (18)0.36201 (9)0.0327 (4)
C140.3082 (3)0.05848 (19)0.41956 (9)0.0343 (4)
H140.34580.10760.45250.041*
C150.1828 (2)0.01806 (18)0.42974 (8)0.0295 (3)
H150.13660.02290.46970.035*
S20.09432 (6)0.27584 (4)0.103954 (18)0.02438 (9)
Cl20.01357 (7)0.22781 (5)0.19394 (2)0.03793 (11)
O40.36056 (16)0.63145 (12)0.05479 (5)0.0276 (2)
O60.06739 (16)0.18020 (12)0.05491 (6)0.0302 (3)
O50.06614 (18)0.33050 (13)0.16777 (6)0.0330 (3)
C170.1952 (2)0.41650 (16)0.06766 (7)0.0237 (3)
C180.1834 (2)0.41055 (16)0.00264 (7)0.0225 (3)
C190.0958 (2)0.30830 (17)0.06083 (8)0.0259 (3)
H190.02370.21460.05970.031*
C200.1199 (2)0.35085 (18)0.11983 (8)0.0271 (3)
C210.2233 (2)0.48782 (19)0.12355 (8)0.0302 (4)
H210.23410.51150.16560.036*
C220.3098 (2)0.58913 (18)0.06623 (8)0.0292 (3)
H220.38080.68310.06740.035*
C230.2875 (2)0.54624 (16)0.00748 (8)0.0246 (3)
C240.3028 (2)0.54992 (17)0.09942 (8)0.0260 (3)
C250.3701 (3)0.62270 (19)0.16990 (8)0.0349 (4)
H25A0.30510.56220.19770.052*
H25B0.33910.71130.17540.052*
H25C0.51050.64290.18340.052*
C260.2726 (2)0.19238 (16)0.11785 (8)0.0245 (3)
C270.2712 (2)0.08041 (17)0.07094 (8)0.0298 (3)
H270.17600.04940.03060.036*
C280.4102 (3)0.01391 (18)0.08349 (9)0.0345 (4)
H280.40800.06430.05180.041*
C290.5527 (2)0.06008 (18)0.14183 (9)0.0326 (4)
C300.5542 (3)0.1749 (2)0.18749 (9)0.0342 (4)
H300.65240.20850.22710.041*
C310.4152 (3)0.24113 (18)0.17622 (8)0.0302 (4)
H310.41680.31910.20800.036*
C320.7015 (3)0.0134 (2)0.15597 (11)0.0444 (5)
H32A0.68960.08380.11660.067*
H32B0.68050.06010.19350.067*
H32C0.83150.05590.16700.067*
C160.5134 (3)0.1492 (2)0.35059 (12)0.0447 (5)
H16A0.43740.24400.32550.067*
H16B0.58480.15590.39350.067*
H16C0.60530.10290.32530.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0559 (3)0.0585 (3)0.0223 (2)0.0277 (2)0.00813 (19)0.00901 (19)
S10.02324 (19)0.02530 (19)0.02250 (18)0.00409 (15)0.00130 (14)0.00326 (14)
O10.0304 (6)0.0251 (6)0.0312 (6)0.0062 (5)0.0083 (5)0.0081 (5)
O20.0275 (6)0.0301 (6)0.0333 (6)0.0037 (5)0.0096 (5)0.0076 (5)
O30.0322 (6)0.0381 (7)0.0267 (6)0.0082 (5)0.0054 (5)0.0031 (5)
C10.0226 (7)0.0242 (7)0.0231 (7)0.0066 (6)0.0031 (6)0.0034 (6)
C20.0203 (7)0.0253 (7)0.0232 (7)0.0085 (6)0.0044 (6)0.0035 (6)
C30.0266 (8)0.0279 (8)0.0245 (7)0.0097 (6)0.0053 (6)0.0055 (6)
C40.0309 (8)0.0401 (9)0.0215 (7)0.0180 (7)0.0041 (6)0.0053 (7)
C50.0288 (8)0.0354 (9)0.0291 (8)0.0125 (7)0.0018 (7)0.0049 (7)
C60.0255 (8)0.0256 (8)0.0376 (9)0.0066 (7)0.0016 (7)0.0017 (7)
C70.0220 (7)0.0264 (8)0.0288 (8)0.0085 (6)0.0064 (6)0.0054 (6)
C80.0266 (8)0.0279 (8)0.0270 (8)0.0093 (6)0.0052 (6)0.0066 (6)
C90.0424 (10)0.0425 (10)0.0281 (8)0.0138 (8)0.0106 (7)0.0159 (8)
C100.0261 (8)0.0208 (7)0.0244 (7)0.0029 (6)0.0032 (6)0.0017 (6)
C110.0367 (9)0.0297 (8)0.0230 (7)0.0062 (7)0.0047 (7)0.0026 (6)
C120.0380 (10)0.0311 (9)0.0295 (8)0.0049 (7)0.0113 (7)0.0017 (7)
C130.0294 (9)0.0213 (8)0.0408 (9)0.0018 (6)0.0071 (7)0.0018 (7)
C140.0361 (9)0.0288 (9)0.0386 (9)0.0098 (7)0.0074 (7)0.0106 (7)
C150.0328 (9)0.0277 (8)0.0273 (8)0.0065 (7)0.0085 (7)0.0079 (6)
S20.02491 (19)0.02583 (19)0.02175 (18)0.00625 (15)0.00545 (14)0.00582 (14)
Cl20.0461 (3)0.0422 (3)0.02349 (19)0.0162 (2)0.00331 (17)0.00018 (17)
O40.0278 (6)0.0234 (6)0.0282 (6)0.0048 (5)0.0039 (5)0.0039 (4)
O60.0248 (6)0.0302 (6)0.0310 (6)0.0032 (5)0.0029 (5)0.0065 (5)
O50.0377 (7)0.0378 (7)0.0258 (6)0.0121 (5)0.0126 (5)0.0070 (5)
C170.0243 (7)0.0247 (7)0.0223 (7)0.0080 (6)0.0047 (6)0.0053 (6)
C180.0206 (7)0.0249 (7)0.0234 (7)0.0086 (6)0.0046 (6)0.0066 (6)
C190.0257 (8)0.0252 (8)0.0255 (7)0.0075 (6)0.0040 (6)0.0045 (6)
C200.0276 (8)0.0325 (8)0.0226 (7)0.0130 (7)0.0047 (6)0.0035 (6)
C210.0323 (9)0.0376 (9)0.0278 (8)0.0159 (7)0.0117 (7)0.0134 (7)
C220.0284 (8)0.0276 (8)0.0347 (9)0.0092 (7)0.0105 (7)0.0113 (7)
C230.0223 (7)0.0252 (8)0.0269 (7)0.0085 (6)0.0052 (6)0.0051 (6)
C240.0251 (8)0.0264 (8)0.0269 (8)0.0090 (6)0.0051 (6)0.0054 (6)
C250.0369 (10)0.0325 (9)0.0279 (8)0.0065 (7)0.0013 (7)0.0017 (7)
C260.0260 (8)0.0232 (7)0.0238 (7)0.0056 (6)0.0048 (6)0.0086 (6)
C270.0290 (8)0.0257 (8)0.0291 (8)0.0045 (7)0.0012 (6)0.0019 (6)
C280.0351 (9)0.0254 (8)0.0414 (10)0.0087 (7)0.0075 (8)0.0039 (7)
C290.0297 (9)0.0289 (8)0.0423 (10)0.0082 (7)0.0093 (7)0.0179 (7)
C300.0330 (9)0.0393 (10)0.0280 (8)0.0092 (8)0.0001 (7)0.0119 (7)
C310.0351 (9)0.0309 (8)0.0222 (7)0.0087 (7)0.0025 (6)0.0056 (6)
C320.0368 (10)0.0415 (11)0.0621 (13)0.0171 (9)0.0106 (9)0.0243 (10)
C160.0392 (11)0.0286 (9)0.0641 (13)0.0088 (8)0.0160 (9)0.0002 (9)
Geometric parameters (Å, º) top
Cl1—C41.7392 (17)S2—C261.7591 (16)
S1—O21.4336 (12)Cl2—C201.7443 (16)
S1—O31.4353 (12)O4—C241.367 (2)
S1—C11.7397 (16)O4—C231.3789 (18)
S1—C101.7607 (16)C17—C241.359 (2)
O1—C81.370 (2)C17—C181.443 (2)
O1—C71.3751 (19)C18—C231.394 (2)
C1—C81.359 (2)C18—C191.400 (2)
C1—C21.447 (2)C19—C201.379 (2)
C2—C71.392 (2)C19—H190.9500
C2—C31.394 (2)C20—C211.396 (2)
C3—C41.386 (2)C21—C221.382 (2)
C3—H30.9500C21—H210.9500
C4—C51.393 (3)C22—C231.373 (2)
C5—C61.376 (3)C22—H220.9500
C5—H50.9500C24—C251.479 (2)
C6—C71.383 (2)C25—H25A0.9800
C6—H60.9500C25—H25B0.9800
C8—C91.478 (2)C25—H25C0.9800
C9—H9A0.9800C26—C271.382 (2)
C9—H9B0.9800C26—C311.392 (2)
C9—H9C0.9800C27—C281.386 (2)
C10—C151.384 (2)C27—H270.9500
C10—C111.390 (2)C28—C291.391 (2)
C11—C121.384 (3)C28—H280.9500
C11—H110.9500C29—C301.389 (3)
C12—C131.387 (3)C29—C321.502 (2)
C12—H120.9500C30—C311.381 (2)
C13—C141.387 (3)C30—H300.9500
C13—C161.505 (3)C31—H310.9500
C14—C151.387 (2)C32—H32A0.9800
C14—H140.9500C32—H32B0.9800
C15—H150.9500C32—H32C0.9800
S2—O61.4351 (12)C16—H16A0.9800
S2—O51.4364 (12)C16—H16B0.9800
S2—C171.7399 (16)C16—H16C0.9800
O2—S1—O3119.75 (8)C24—O4—C23106.77 (12)
O2—S1—C1106.70 (7)C24—C17—C18107.37 (14)
O3—S1—C1108.68 (8)C24—C17—S2127.08 (12)
O2—S1—C10107.90 (8)C18—C17—S2125.53 (12)
O3—S1—C10107.69 (7)C23—C18—C19119.07 (14)
C1—S1—C10105.23 (7)C23—C18—C17104.74 (13)
C8—O1—C7106.81 (12)C19—C18—C17136.18 (15)
C8—C1—C2107.30 (14)C20—C19—C18116.46 (15)
C8—C1—S1127.15 (12)C20—C19—H19121.8
C2—C1—S1125.53 (12)C18—C19—H19121.8
C7—C2—C3119.56 (14)C19—C20—C21123.49 (15)
C7—C2—C1104.64 (14)C19—C20—Cl2118.42 (13)
C3—C2—C1135.79 (15)C21—C20—Cl2118.08 (13)
C4—C3—C2116.34 (15)C22—C21—C20120.25 (15)
C4—C3—H3121.8C22—C21—H21119.9
C2—C3—H3121.8C20—C21—H21119.9
C3—C4—C5123.26 (16)C23—C22—C21116.20 (16)
C3—C4—Cl1118.16 (14)C23—C22—H22121.9
C5—C4—Cl1118.58 (13)C21—C22—H22121.9
C6—C5—C4120.66 (15)C22—C23—O4125.08 (15)
C6—C5—H5119.7C22—C23—C18124.52 (15)
C4—C5—H5119.7O4—C23—C18110.39 (13)
C5—C6—C7116.12 (16)C17—C24—O4110.74 (14)
C5—C6—H6121.9C17—C24—C25134.29 (16)
C7—C6—H6121.9O4—C24—C25114.97 (14)
O1—C7—C6125.33 (15)C24—C25—H25A109.5
O1—C7—C2110.61 (13)C24—C25—H25B109.5
C6—C7—C2124.05 (16)H25A—C25—H25B109.5
C1—C8—O1110.64 (14)C24—C25—H25C109.5
C1—C8—C9134.21 (16)H25A—C25—H25C109.5
O1—C8—C9115.13 (15)H25B—C25—H25C109.5
C8—C9—H9A109.5C27—C26—C31120.64 (15)
C8—C9—H9B109.5C27—C26—S2120.14 (12)
H9A—C9—H9B109.5C31—C26—S2119.21 (12)
C8—C9—H9C109.5C26—C27—C28119.28 (15)
H9A—C9—H9C109.5C26—C27—H27120.4
H9B—C9—H9C109.5C28—C27—H27120.4
C15—C10—C11120.71 (16)C27—C28—C29120.96 (16)
C15—C10—S1119.69 (13)C27—C28—H28119.5
C11—C10—S1119.59 (13)C29—C28—H28119.5
C12—C11—C10118.78 (16)C30—C29—C28118.75 (16)
C12—C11—H11120.6C30—C29—C32120.25 (17)
C10—C11—H11120.6C28—C29—C32121.00 (17)
C11—C12—C13121.53 (16)C31—C30—C29121.04 (16)
C11—C12—H12119.2C31—C30—H30119.5
C13—C12—H12119.2C29—C30—H30119.5
C14—C13—C12118.62 (16)C30—C31—C26119.30 (16)
C14—C13—C16120.84 (18)C30—C31—H31120.3
C12—C13—C16120.53 (17)C26—C31—H31120.4
C13—C14—C15120.90 (17)C29—C32—H32A109.5
C13—C14—H14119.5C29—C32—H32B109.5
C15—C14—H14119.5H32A—C32—H32B109.5
C10—C15—C14119.43 (16)C29—C32—H32C109.5
C10—C15—H15120.3H32A—C32—H32C109.5
C14—C15—H15120.3H32B—C32—H32C109.5
O6—S2—O5119.79 (7)C13—C16—H16A109.5
O6—S2—C17106.81 (7)C13—C16—H16B109.5
O5—S2—C17108.76 (8)H16A—C16—H16B109.5
O6—S2—C26107.88 (7)C13—C16—H16C109.5
O5—S2—C26107.38 (7)H16A—C16—H16C109.5
C17—S2—C26105.33 (7)H16B—C16—H16C109.5
O2—S1—C1—C8157.13 (14)O6—S2—C17—C24155.68 (14)
O3—S1—C1—C826.72 (17)O5—S2—C17—C2425.08 (17)
C10—S1—C1—C888.40 (16)C26—S2—C17—C2489.78 (15)
O2—S1—C1—C225.03 (15)O6—S2—C17—C1826.17 (15)
O3—S1—C1—C2155.44 (13)O5—S2—C17—C18156.77 (13)
C10—S1—C1—C289.44 (14)C26—S2—C17—C1888.37 (14)
C8—C1—C2—C70.54 (17)C24—C17—C18—C230.43 (17)
S1—C1—C2—C7178.73 (12)S2—C17—C18—C23178.88 (11)
C8—C1—C2—C3179.77 (17)C24—C17—C18—C19179.32 (17)
S1—C1—C2—C32.0 (3)S2—C17—C18—C192.2 (3)
C7—C2—C3—C40.1 (2)C23—C18—C19—C200.1 (2)
C1—C2—C3—C4179.20 (16)C17—C18—C19—C20178.70 (16)
C2—C3—C4—C50.7 (2)C18—C19—C20—C210.6 (2)
C2—C3—C4—Cl1179.93 (11)C18—C19—C20—Cl2179.89 (11)
C3—C4—C5—C60.6 (3)C19—C20—C21—C220.6 (2)
Cl1—C4—C5—C6179.89 (13)Cl2—C20—C21—C22179.89 (13)
C4—C5—C6—C70.3 (2)C20—C21—C22—C230.1 (2)
C8—O1—C7—C6178.94 (15)C21—C22—C23—O4179.20 (14)
C8—O1—C7—C20.19 (17)C21—C22—C23—C180.8 (2)
C5—C6—C7—O1179.58 (14)C24—O4—C23—C22178.55 (15)
C5—C6—C7—C21.0 (2)C24—O4—C23—C180.02 (16)
C3—C2—C7—O1179.60 (13)C19—C18—C23—C220.8 (2)
C1—C2—C7—O10.21 (16)C17—C18—C23—C22178.31 (15)
C3—C2—C7—C60.8 (2)C19—C18—C23—O4179.40 (13)
C1—C2—C7—C6178.56 (15)C17—C18—C23—O40.28 (16)
C2—C1—C8—O10.68 (18)C18—C17—C24—O40.44 (17)
S1—C1—C8—O1178.84 (11)S2—C17—C24—O4178.86 (11)
C2—C1—C8—C9177.70 (18)C18—C17—C24—C25178.78 (17)
S1—C1—C8—C90.5 (3)S2—C17—C24—C250.4 (3)
C7—O1—C8—C10.55 (17)C23—O4—C24—C170.27 (17)
C7—O1—C8—C9178.17 (14)C23—O4—C24—C25179.12 (13)
O2—S1—C10—C1519.93 (15)O6—S2—C26—C2720.41 (16)
O3—S1—C10—C15150.50 (13)O5—S2—C26—C27150.81 (14)
C1—S1—C10—C1593.70 (14)C17—S2—C26—C2793.39 (15)
O2—S1—C10—C11160.40 (13)O6—S2—C26—C31160.06 (13)
O3—S1—C10—C1129.84 (15)O5—S2—C26—C3129.66 (15)
C1—S1—C10—C1185.96 (14)C17—S2—C26—C3186.14 (14)
C15—C10—C11—C120.1 (2)C31—C26—C27—C282.0 (3)
S1—C10—C11—C12179.74 (13)S2—C26—C27—C28178.50 (13)
C10—C11—C12—C131.2 (3)C26—C27—C28—C291.3 (3)
C11—C12—C13—C141.3 (3)C27—C28—C29—C300.3 (3)
C11—C12—C13—C16177.91 (17)C27—C28—C29—C32179.02 (17)
C12—C13—C14—C150.1 (3)C28—C29—C30—C311.2 (3)
C16—C13—C14—C15179.11 (17)C32—C29—C30—C31178.07 (17)
C11—C10—C15—C141.2 (2)C29—C30—C31—C260.6 (3)
S1—C10—C15—C14179.10 (13)C27—C26—C31—C301.1 (3)
C13—C14—C15—C101.2 (3)S2—C26—C31—C30179.42 (13)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C26–C31 ring.
D—H···AD—HH···AD···AD—H···A
C15—H15···O2i0.952.563.251 (2)130
C27—H27···O6ii0.952.553.248 (2)131
C30—H30···O3iii0.952.483.361 (2)154
C22—H22···Cgiv0.952.713.572 (2)136
Symmetry codes: (i) x, y, z+1; (ii) x, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H13ClO3S
Mr320.77
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.3725 (2), 10.0967 (3), 20.8173 (7)
α, β, γ (°)98.086 (1), 99.547 (2), 106.547 (1)
V3)1435.62 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.41 × 0.29 × 0.23
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.670, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
26328, 7109, 5967
Rint0.028
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.098, 1.04
No. of reflections7109
No. of parameters383
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C26–C31 ring.
D—H···AD—HH···AD···AD—H···A
C15—H15···O2i0.952.563.251 (2)130.0
C27—H27···O6ii0.952.553.248 (2)130.7
C30—H30···O3iii0.952.483.361 (2)153.9
C22—H22···Cgiv0.952.713.572 (2)135.7
Symmetry codes: (i) x, y, z+1; (ii) x, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

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. & Lee, U. (2012). Acta Cryst. E68, o2027.  CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2350.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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