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-ethyl­sulfinyl-2-(3-fluoro­phen­yl)-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 10 June 2013; accepted 1 July 2013; online 6 July 2013)

The asymmetric unit of the title compound, C16H12ClFO2S, contains two independent mol­ecules in which the benzo­furan ring systems are essentially planar, with r.m.s. deviations of 0.007 (1) and 0.013 (1) Å. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds into chains extending along the b axis. These chains are further packed into stacks along the c -axis by S⋯O contacts [3.1898 (11) and 3.1361 (11) Å] involving the sulfinyl groups. In both 3-fluoro­phenyl rings, the F atom is disordered over two positions, with site-occupancy factors of 0.921 (2) and 0.079 (2).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o402.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2449.]). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2008[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1061.]). For a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998[Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12ClFO2S

  • Mr = 322.77

  • Triclinic, [P \overline 1]

  • a = 9.5538 (5) Å

  • b = 11.2638 (5) Å

  • c = 13.4079 (6) Å

  • α = 98.739 (2)°

  • β = 93.733 (3)°

  • γ = 98.627 (2)°

  • V = 1404.25 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 173 K

  • 0.39 × 0.30 × 0.13 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 = 0.625, Tmax = 0.746

  • 24991 measured reflections

  • 6456 independent reflections

  • 5012 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.102

  • S = 1.06

  • 6456 reflections

  • 390 parameters

  • 16 restraints

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15B⋯O4 0.99 2.28 3.233 (2) 160
C31—H31B⋯O2i 0.99 2.26 3.211 (2) 160
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 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-3-ethylsulfinyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2010a) and 4-iodophenyl (Choi et al., 2010b) substituents in 2-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 0.007 (1) and 0.013 (1) Å, for A and B molecule, respectively, from the least-squares plane defined by the nine constituent atoms. In the 3-fluorophenyl rings of both molecules, the F atoms are disordered over two positions with site-occupancy factors, from refinement of 0.921 (2) (part A) and 0.079 (2) (part B). The dihedral angles between the 3-fluorophenyl ring and the mean plane of the benzofuran ring system are 15.35 (8)° in the molecule A and 5.62 (9)° in the molecule B, respectively. In the crystal packing (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1) into chains extending along the b-axis direction.

In the crystal packing (Fig. 2), these chains are further packed into stacks along the c-axis by a sulfinyl–sulfinyl interaction (Choi et al., 2008) interpreted as similar to a type-Il carbonyl–carbonyl interaction (Allen et al., 1998), with S1···O4iii and S2···O2iii distances of 3.1898 (11) and 3.1361 (11) Å (symmetry code iii: - x + 1,- y + 1,- z + 1).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2008). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998).

Experimental top

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-chloro-3-ethylsulfanyl-2-(3-fluorophenyl)-1-benzofuran (337 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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 67%, m.p. 390–391 K; Rf = 0.59 (hexane–ethyl acetate, 24:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone 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, 0.99 Å for methylene and 0.98Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl and methylene, and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally. The F1 and F2 atoms of the 3-fluorophenyl rings are disordered over two positions with site occupancy factors, from refinement of 0.921 (2) (part A) and 0.079 (2) (part B). For the proper treatment of H-atoms, carbon atoms C11 and C13 (molecule A), and C27 and C29 (molecule B) were divided in two parts with equalized coordinates and thermal parameters. The distance of equivalent C–F pairs were restrained to 1.330 (5) Å using command DFIX, and displacement ellipsoids of F1 and F2 sets were restrained to 0.01 using command ISOR.

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. H atoms are presented as small spheres of arbitrary radius. The F atom of the 3-fluorophenyl ring is disordered over two positions with site occupancy factors, from refinement of 0.921 (2) (part A) and 0.079 (2) (part B).
[Figure 2] Fig. 2. A view of the C—H···O and S···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding and disordered part B atoms were omitted for clarity. [Symmetry codes: (i) x, y + 1, z; (ii) x, y - 1, z; (iii) - x + 1, - y + 1, - z + 1.]
5-Chloro-3-ethylsulfinyl-2-(3-fluorophenyl)-1-benzofuran top
Crystal data top
C16H12ClFO2SZ = 4
Mr = 322.77F(000) = 664
Triclinic, P1Dx = 1.527 Mg m3
Hall symbol: -P 1Melting point = 390–391 K
a = 9.5538 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.2638 (5) ÅCell parameters from 7946 reflections
c = 13.4079 (6) Åθ = 2.5–27.5°
α = 98.739 (2)°µ = 0.43 mm1
β = 93.733 (3)°T = 173 K
γ = 98.627 (2)°Block, colourless
V = 1404.25 (12) Å30.39 × 0.30 × 0.13 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
6456 independent reflections
Radiation source: rotating anode5012 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.039
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.5°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1414
Tmin = 0.625, Tmax = 0.746l = 1717
24991 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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.102H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0489P)2 + 0.2168P]
where P = (Fo2 + 2Fc2)/3
6456 reflections(Δ/σ)max < 0.001
390 parametersΔρmax = 0.35 e Å3
16 restraintsΔρmin = 0.38 e Å3
Crystal data top
C16H12ClFO2Sγ = 98.627 (2)°
Mr = 322.77V = 1404.25 (12) Å3
Triclinic, P1Z = 4
a = 9.5538 (5) ÅMo Kα radiation
b = 11.2638 (5) ŵ = 0.43 mm1
c = 13.4079 (6) ÅT = 173 K
α = 98.739 (2)°0.39 × 0.30 × 0.13 mm
β = 93.733 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
6456 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5012 reflections with I > 2σ(I)
Tmin = 0.625, Tmax = 0.746Rint = 0.039
24991 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03816 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.06Δρmax = 0.35 e Å3
6456 reflectionsΔρmin = 0.38 e Å3
390 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*/UeqOcc. (<1)
Cl10.13450 (5)0.12001 (5)0.30389 (4)0.04416 (14)
S10.38869 (4)0.27480 (4)0.39795 (3)0.02455 (11)
O10.17196 (11)0.27468 (11)0.13349 (7)0.0289 (3)
O20.35241 (13)0.16152 (11)0.44212 (9)0.0352 (3)
C10.26850 (16)0.25654 (15)0.28734 (11)0.0233 (3)
C20.14620 (16)0.16187 (15)0.26000 (11)0.0242 (3)
C30.07727 (16)0.06820 (15)0.30474 (12)0.0275 (4)
H30.11020.05470.36980.033*
C40.04107 (17)0.00427 (16)0.25041 (12)0.0306 (4)
C50.09163 (18)0.01253 (17)0.15403 (13)0.0347 (4)
H50.17260.04040.11910.042*
C60.02470 (18)0.10514 (17)0.10986 (12)0.0329 (4)
H60.05760.11850.04470.039*
C70.09267 (17)0.17788 (16)0.16478 (11)0.0271 (4)
C80.28051 (16)0.32102 (15)0.20894 (11)0.0253 (4)
C90.37654 (16)0.42621 (16)0.18878 (11)0.0248 (3)
C100.50720 (17)0.46966 (17)0.24506 (11)0.0310 (4)
H100.53740.42890.29760.037*
C11A0.59270 (18)0.57172 (17)0.22454 (12)0.0331 (4)0.9214 (19)
H110.68110.60040.26370.040*0.9214 (19)
C11B0.59270 (18)0.57172 (17)0.22454 (12)0.0331 (4)0.08
F1B0.7030 (8)0.6258 (10)0.2897 (7)0.030 (3)*0.0786 (19)
C120.55272 (18)0.63305 (17)0.14834 (12)0.0338 (4)
H120.61150.70340.13450.041*
C13A0.42413 (19)0.58787 (17)0.09344 (12)0.0348 (4)0.9214 (19)
F1A0.37983 (13)0.64640 (12)0.01946 (9)0.0534 (4)0.9214 (19)
C13B0.42413 (19)0.58787 (17)0.09344 (12)0.0348 (4)0.08
H13B0.39510.62860.04050.042*0.0786 (19)
C140.33604 (18)0.48750 (16)0.11115 (12)0.0316 (4)
H140.24810.45960.07110.038*
C150.31917 (18)0.39296 (15)0.47604 (11)0.0293 (4)
H15A0.38040.41770.54050.035*
H15B0.32330.46470.44120.035*
C160.16734 (19)0.3549 (2)0.49948 (13)0.0426 (5)
H16A0.10390.34130.43700.064*
H16B0.13960.41930.54830.064*
H16C0.16040.27960.52830.064*
S20.40317 (4)0.78265 (4)0.38140 (3)0.02374 (11)
Cl20.11295 (5)0.38426 (4)0.27511 (3)0.03871 (13)
O30.17390 (12)0.80626 (11)0.12789 (8)0.0301 (3)
O40.37877 (12)0.66012 (11)0.41197 (8)0.0330 (3)
C170.27717 (16)0.77503 (15)0.27571 (11)0.0234 (3)
C180.15482 (16)0.68113 (15)0.24602 (11)0.0249 (3)
C190.09085 (16)0.58064 (15)0.28519 (11)0.0262 (4)
H190.12700.56160.34750.031*
C200.02740 (17)0.51006 (16)0.22934 (12)0.0288 (4)
C210.08279 (18)0.53538 (18)0.13732 (12)0.0344 (4)
H210.16380.48360.10130.041*
C220.02113 (18)0.63453 (18)0.09858 (12)0.0356 (4)
H220.05780.65350.03640.043*
C230.09697 (17)0.70541 (16)0.15460 (11)0.0281 (4)
C240.28570 (16)0.84678 (16)0.20190 (11)0.0254 (4)
C250.38173 (16)0.95328 (15)0.18337 (11)0.0244 (3)
C260.50607 (17)1.00255 (17)0.24596 (11)0.0305 (4)
H260.53040.96700.30320.037*
C27A0.59358 (18)1.10291 (17)0.22457 (12)0.0321 (4)0.9214 (19)
H27A0.67811.13520.26750.039*0.9214 (19)
C27B0.59358 (18)1.10291 (17)0.22457 (12)0.0321 (4)0.08
F2B0.7032 (9)1.1542 (11)0.2920 (7)0.032 (3)*0.0786 (19)
C280.56134 (18)1.15759 (16)0.14231 (12)0.0322 (4)
H280.62171.22680.12790.039*
C29A0.43791 (19)1.10749 (17)0.08194 (11)0.0315 (4)0.9214 (19)
F2A0.40153 (13)1.15850 (12)0.00136 (9)0.0489 (4)0.9214 (19)
C29B0.43791 (19)1.10749 (17)0.08194 (11)0.0315 (4)0.08
H29B0.41371.14400.02520.038*0.0786 (19)
C300.34884 (17)1.00771 (16)0.09992 (11)0.0289 (4)
H300.26530.97570.05600.035*
C310.32775 (18)0.88245 (16)0.47356 (11)0.0300 (4)
H31A0.39240.90230.53670.036*
H31B0.32160.95940.44760.036*
C320.18165 (19)0.8292 (2)0.49831 (13)0.0429 (5)
H32A0.11390.81950.43840.064*
H32B0.15150.88390.55390.064*
H32C0.18490.74960.51870.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0380 (3)0.0344 (3)0.0567 (3)0.0087 (2)0.0048 (2)0.0149 (2)
S10.0232 (2)0.0241 (2)0.02548 (18)0.00255 (18)0.00470 (14)0.00573 (16)
O10.0275 (6)0.0343 (7)0.0229 (5)0.0012 (5)0.0040 (4)0.0070 (5)
O20.0408 (7)0.0226 (6)0.0411 (6)0.0019 (6)0.0127 (5)0.0119 (5)
C10.0205 (8)0.0241 (9)0.0239 (7)0.0019 (7)0.0016 (6)0.0025 (6)
C20.0215 (8)0.0243 (9)0.0255 (7)0.0042 (7)0.0005 (6)0.0007 (7)
C30.0264 (8)0.0269 (9)0.0290 (7)0.0054 (8)0.0013 (6)0.0043 (7)
C40.0265 (9)0.0249 (9)0.0386 (9)0.0010 (8)0.0009 (7)0.0036 (8)
C50.0275 (9)0.0344 (11)0.0363 (9)0.0016 (8)0.0065 (7)0.0022 (8)
C60.0295 (9)0.0370 (11)0.0284 (8)0.0006 (8)0.0056 (7)0.0028 (8)
C70.0247 (8)0.0291 (9)0.0256 (7)0.0010 (8)0.0003 (6)0.0031 (7)
C80.0237 (8)0.0284 (9)0.0217 (7)0.0031 (7)0.0025 (6)0.0007 (7)
C90.0249 (8)0.0276 (9)0.0215 (7)0.0036 (7)0.0031 (6)0.0026 (7)
C100.0297 (9)0.0363 (10)0.0264 (7)0.0022 (8)0.0006 (6)0.0078 (7)
C11A0.0258 (9)0.0396 (11)0.0308 (8)0.0028 (8)0.0004 (7)0.0051 (8)
C11B0.0258 (9)0.0396 (11)0.0308 (8)0.0028 (8)0.0004 (7)0.0051 (8)
C120.0333 (9)0.0322 (10)0.0345 (8)0.0017 (8)0.0066 (7)0.0070 (8)
C13A0.0372 (10)0.0347 (11)0.0332 (8)0.0036 (9)0.0002 (7)0.0110 (8)
F1A0.0534 (8)0.0501 (8)0.0576 (8)0.0056 (7)0.0120 (6)0.0330 (7)
C13B0.0372 (10)0.0347 (11)0.0332 (8)0.0036 (9)0.0002 (7)0.0110 (8)
C140.0295 (9)0.0328 (10)0.0305 (8)0.0018 (8)0.0049 (7)0.0057 (8)
C150.0364 (9)0.0222 (9)0.0272 (7)0.0036 (8)0.0045 (6)0.0015 (7)
C160.0401 (10)0.0538 (14)0.0330 (9)0.0109 (10)0.0054 (8)0.0005 (9)
S20.0216 (2)0.0232 (2)0.02581 (18)0.00206 (17)0.00403 (14)0.00636 (16)
Cl20.0344 (2)0.0282 (2)0.0503 (3)0.0054 (2)0.00282 (19)0.0093 (2)
O30.0279 (6)0.0360 (7)0.0233 (5)0.0045 (6)0.0051 (4)0.0084 (5)
O40.0357 (7)0.0216 (6)0.0410 (6)0.0048 (6)0.0089 (5)0.0084 (5)
C170.0208 (8)0.0243 (9)0.0233 (7)0.0010 (7)0.0019 (6)0.0025 (6)
C180.0223 (8)0.0271 (9)0.0235 (7)0.0027 (7)0.0002 (6)0.0005 (7)
C190.0245 (8)0.0245 (9)0.0285 (7)0.0020 (7)0.0012 (6)0.0037 (7)
C200.0254 (8)0.0253 (9)0.0334 (8)0.0005 (8)0.0026 (6)0.0018 (7)
C210.0279 (9)0.0379 (11)0.0314 (8)0.0052 (8)0.0046 (7)0.0002 (8)
C220.0317 (9)0.0431 (12)0.0276 (8)0.0041 (9)0.0071 (7)0.0064 (8)
C230.0264 (8)0.0306 (10)0.0248 (7)0.0022 (8)0.0007 (6)0.0048 (7)
C240.0220 (8)0.0302 (9)0.0219 (7)0.0025 (7)0.0012 (6)0.0015 (7)
C250.0245 (8)0.0261 (9)0.0218 (7)0.0036 (7)0.0028 (6)0.0023 (7)
C260.0300 (9)0.0350 (10)0.0250 (7)0.0001 (8)0.0014 (6)0.0069 (7)
C27A0.0273 (9)0.0352 (11)0.0301 (8)0.0023 (8)0.0027 (7)0.0030 (8)
C27B0.0273 (9)0.0352 (11)0.0301 (8)0.0023 (8)0.0027 (7)0.0030 (8)
C280.0331 (9)0.0281 (10)0.0347 (8)0.0006 (8)0.0087 (7)0.0065 (8)
C29A0.0356 (10)0.0327 (10)0.0278 (8)0.0057 (8)0.0020 (7)0.0101 (7)
F2A0.0538 (8)0.0487 (8)0.0449 (6)0.0046 (6)0.0063 (5)0.0272 (6)
C29B0.0356 (10)0.0327 (10)0.0278 (8)0.0057 (8)0.0020 (7)0.0101 (7)
C300.0285 (9)0.0313 (10)0.0261 (7)0.0028 (8)0.0013 (6)0.0055 (7)
C310.0354 (9)0.0245 (9)0.0271 (7)0.0049 (8)0.0062 (6)0.0011 (7)
C320.0381 (10)0.0522 (13)0.0365 (9)0.0083 (10)0.0069 (8)0.0015 (9)
Geometric parameters (Å, º) top
Cl1—C41.7403 (18)S2—O41.4882 (12)
S1—O21.4909 (12)S2—C171.7818 (14)
S1—C11.7818 (14)S2—C311.8018 (16)
S1—C151.8003 (16)S2—O2i3.1361 (11)
S1—O4i3.1898 (11)Cl2—C201.7420 (18)
O1—C71.368 (2)O3—C231.366 (2)
O1—C81.3827 (17)O3—C241.3828 (17)
C1—C81.367 (2)C17—C241.368 (2)
C1—C21.445 (2)C17—C181.444 (2)
C2—C71.392 (2)C18—C231.394 (2)
C2—C31.394 (2)C18—C191.395 (2)
C3—C41.382 (2)C19—C201.381 (2)
C3—H30.9500C19—H190.9500
C4—C51.400 (2)C20—C211.397 (2)
C5—C61.373 (3)C21—C221.372 (3)
C5—H50.9500C21—H210.9500
C6—C71.380 (2)C22—C231.383 (2)
C6—H60.9500C22—H220.9500
C8—C91.457 (2)C24—C251.460 (2)
C9—C101.396 (2)C25—C301.395 (2)
C9—C141.398 (2)C25—C261.398 (2)
C10—C11A1.381 (2)C26—C27A1.380 (2)
C10—H100.9500C26—H260.9500
C11A—C121.382 (2)C27A—C281.382 (2)
C11A—H110.9500C27A—H27A0.9500
C12—C13A1.375 (2)C28—C29A1.379 (2)
C12—H120.9500C28—H280.9500
C13A—F1A1.3511 (18)C29A—F2A1.3483 (17)
C13A—C141.366 (2)C29A—C301.367 (2)
C14—H140.9500C30—H300.9500
C15—C161.517 (2)C31—C321.513 (2)
C15—H15A0.9900C31—H31A0.9900
C15—H15B0.9900C31—H31B0.9900
C16—H16A0.9800C32—H32A0.9800
C16—H16B0.9800C32—H32B0.9800
C16—H16C0.9800C32—H32C0.9800
O2—S1—C1105.42 (7)O4—S2—C17105.65 (7)
O2—S1—C15106.75 (8)O4—S2—C31106.46 (8)
C1—S1—C1599.12 (7)C17—S2—C3198.92 (7)
O2—S1—O4i81.93 (5)O4—S2—O2i83.93 (5)
C1—S1—O4i172.64 (6)C17—S2—O2i170.27 (6)
C15—S1—O4i78.70 (5)C31—S2—O2i79.57 (6)
C7—O1—C8106.76 (12)C23—O3—C24106.83 (12)
C8—C1—C2107.21 (13)C24—C17—C18107.22 (13)
C8—C1—S1127.12 (13)C24—C17—S2127.16 (13)
C2—C1—S1125.44 (12)C18—C17—S2125.23 (12)
C7—C2—C3118.94 (14)C23—C18—C19119.15 (14)
C7—C2—C1104.89 (14)C23—C18—C17104.89 (14)
C3—C2—C1136.17 (14)C19—C18—C17135.95 (14)
C4—C3—C2117.18 (14)C20—C19—C18117.03 (14)
C4—C3—H3121.4C20—C19—H19121.5
C2—C3—H3121.4C18—C19—H19121.5
C3—C4—C5122.81 (16)C19—C20—C21122.87 (16)
C3—C4—Cl1119.26 (13)C19—C20—Cl2119.11 (13)
C5—C4—Cl1117.91 (13)C21—C20—Cl2118.02 (13)
C6—C5—C4120.26 (16)C22—C21—C20120.49 (15)
C6—C5—H5119.9C22—C21—H21119.8
C4—C5—H5119.9C20—C21—H21119.8
C5—C6—C7116.70 (15)C21—C22—C23116.67 (15)
C5—C6—H6121.7C21—C22—H22121.7
C7—C6—H6121.7C23—C22—H22121.7
O1—C7—C6124.97 (14)O3—C23—C22125.29 (14)
O1—C7—C2110.93 (13)O3—C23—C18110.92 (14)
C6—C7—C2124.10 (16)C22—C23—C18123.78 (16)
C1—C8—O1110.19 (14)C17—C24—O3110.12 (14)
C1—C8—C9135.22 (14)C17—C24—C25135.92 (14)
O1—C8—C9114.56 (13)O3—C24—C25113.97 (13)
C10—C9—C14118.43 (16)C30—C25—C26118.65 (16)
C10—C9—C8122.51 (14)C30—C25—C24118.94 (14)
C14—C9—C8119.05 (15)C26—C25—C24122.41 (14)
C11A—C10—C9120.21 (15)C27A—C26—C25120.02 (15)
C11A—C10—H10119.9C27A—C26—H26120.0
C9—C10—H10119.9C25—C26—H26120.0
C10—C11A—C12121.57 (16)C26—C27A—C28121.64 (16)
C10—C11A—H11119.2C26—C27A—H27A119.2
C12—C11A—H11119.2C28—C27A—H27A119.2
C13A—C12—C11A117.11 (17)C29A—C28—C27A117.21 (17)
C13A—C12—H12121.4C29A—C28—H28121.4
C11A—C12—H12121.4C27A—C28—H28121.4
F1A—C13A—C14117.61 (15)F2A—C29A—C30117.67 (15)
F1A—C13A—C12119.02 (17)F2A—C29A—C28119.27 (16)
C14—C13A—C12123.35 (16)C30—C29A—C28123.06 (15)
C13A—C14—C9119.32 (16)C29A—C30—C25119.42 (15)
C13A—C14—H14120.3C29A—C30—H30120.3
C9—C14—H14120.3C25—C30—H30120.3
C16—C15—S1113.45 (12)C32—C31—S2113.71 (12)
C16—C15—H15A108.9C32—C31—H31A108.8
S1—C15—H15A108.9S2—C31—H31A108.8
C16—C15—H15B108.9C32—C31—H31B108.8
S1—C15—H15B108.9S2—C31—H31B108.8
H15A—C15—H15B107.7H31A—C31—H31B107.7
C15—C16—H16A109.5C31—C32—H32A109.5
C15—C16—H16B109.5C31—C32—H32B109.5
H16A—C16—H16B109.5H32A—C32—H32B109.5
C15—C16—H16C109.5C31—C32—H32C109.5
H16A—C16—H16C109.5H32A—C32—H32C109.5
H16B—C16—H16C109.5H32B—C32—H32C109.5
O2—S1—C1—C8163.19 (14)O4—S2—C17—C24156.94 (14)
C15—S1—C1—C886.50 (16)C31—S2—C17—C2493.07 (15)
O2—S1—C1—C210.59 (15)O4—S2—C17—C1815.04 (15)
C15—S1—C1—C299.72 (14)C31—S2—C17—C1894.95 (14)
C8—C1—C2—C70.25 (17)C24—C17—C18—C230.64 (17)
S1—C1—C2—C7175.06 (12)S2—C17—C18—C23173.96 (12)
C8—C1—C2—C3179.73 (17)C24—C17—C18—C19178.21 (17)
S1—C1—C2—C35.5 (3)S2—C17—C18—C194.9 (3)
C7—C2—C3—C40.4 (2)C23—C18—C19—C200.4 (2)
C1—C2—C3—C4179.85 (17)C17—C18—C19—C20178.33 (17)
C2—C3—C4—C50.6 (2)C18—C19—C20—C210.2 (2)
C2—C3—C4—Cl1178.21 (12)C18—C19—C20—Cl2179.33 (12)
C3—C4—C5—C61.0 (3)C19—C20—C21—C220.7 (3)
Cl1—C4—C5—C6177.79 (14)Cl2—C20—C21—C22178.87 (14)
C4—C5—C6—C70.4 (3)C20—C21—C22—C230.5 (3)
C8—O1—C7—C6178.81 (16)C24—O3—C23—C22177.52 (16)
C8—O1—C7—C21.10 (17)C24—O3—C23—C181.39 (18)
C5—C6—C7—O1179.50 (15)C21—C22—C23—O3178.95 (16)
C5—C6—C7—C20.6 (3)C21—C22—C23—C180.2 (3)
C3—C2—C7—O1179.06 (13)C19—C18—C23—O3179.56 (13)
C1—C2—C7—O10.53 (17)C17—C18—C23—O30.47 (18)
C3—C2—C7—C61.0 (2)C19—C18—C23—C220.6 (3)
C1—C2—C7—C6179.38 (16)C17—C18—C23—C22178.46 (16)
C2—C1—C8—O10.93 (18)C18—C17—C24—O31.52 (17)
S1—C1—C8—O1175.63 (11)S2—C17—C24—O3174.67 (11)
C2—C1—C8—C9178.96 (17)C18—C17—C24—C25178.78 (17)
S1—C1—C8—C96.3 (3)S2—C17—C24—C255.6 (3)
C7—O1—C8—C11.25 (17)C23—O3—C24—C171.81 (17)
C7—O1—C8—C9179.72 (13)C23—O3—C24—C25178.42 (13)
C1—C8—C9—C1015.5 (3)C17—C24—C25—C30175.60 (17)
O1—C8—C9—C10166.56 (14)O3—C24—C25—C304.1 (2)
C1—C8—C9—C14163.57 (18)C17—C24—C25—C264.7 (3)
O1—C8—C9—C1414.4 (2)O3—C24—C25—C26175.58 (14)
C14—C9—C10—C11A0.7 (2)C30—C25—C26—C27A0.1 (2)
C8—C9—C10—C11A178.31 (15)C24—C25—C26—C27A179.58 (15)
C9—C10—C11A—C120.3 (3)C25—C26—C27A—C280.4 (3)
C10—C11A—C12—C13A0.2 (3)C26—C27A—C28—C29A0.2 (3)
C11A—C12—C13A—F1A178.81 (16)C27A—C28—C29A—F2A179.40 (16)
C11A—C12—C13A—C140.3 (3)C27A—C28—C29A—C300.3 (3)
F1A—C13A—C14—C9178.42 (15)F2A—C29A—C30—C25179.12 (14)
C12—C13A—C14—C90.1 (3)C28—C29A—C30—C250.6 (3)
C10—C9—C14—C13A0.6 (2)C26—C25—C30—C29A0.4 (2)
C8—C9—C14—C13A178.48 (15)C24—C25—C30—C29A179.94 (15)
O2—S1—C15—C1646.90 (13)O4—S2—C31—C3245.51 (14)
C1—S1—C15—C1662.34 (13)C17—S2—C31—C3263.82 (14)
O4i—S1—C15—C16124.80 (12)O2i—S2—C31—C32125.93 (13)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···O40.992.283.233 (2)160
C31—H31B···O2ii0.992.263.211 (2)160
Symmetry code: (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H12ClFO2S
Mr322.77
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.5538 (5), 11.2638 (5), 13.4079 (6)
α, β, γ (°)98.739 (2), 93.733 (3), 98.627 (2)
V3)1404.25 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.43
Crystal size (mm)0.39 × 0.30 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.625, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
24991, 6456, 5012
Rint0.039
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.102, 1.06
No. of reflections6456
No. of parameters390
No. of restraints16
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.38

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
D—H···AD—HH···AD···AD—H···A
C15—H15B···O40.992.283.233 (2)160
C31—H31B···O2i0.992.263.211 (2)160
Symmetry code: (i) x, 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 citationAllen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329.  Web of Science CrossRef CAS IUCr Journals
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. (2008). Acta Cryst. E64, o1061.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o402.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2449.  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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