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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 67| Part 7| July 2011| Page o1557
doi:10.1107/S1600536811019775

5-Chloro-3-cyclo­pentyl­sulfinyl-2-methyl-1-benzo­furan

Pil Ja Seo,a Hong Dae Choi,a Byeng Wha Sonb 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

(Received 17 May 2011; accepted 25 May 2011; online 4 June 2011)

In the title compound, C14H15ClO2S, the cyclo­pentyl ring adopts an envelope conformation. In the crystal, mol­ecules are linked through weak inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits a slipped π–π inter­action between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.784 (3) Å, inter­planar distance = 3.199 (3) Å and slippage = 2.021 (3) Å].

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.]); 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 a structural study of the related compound, 5-bromo-3-cyclo­pentyl­sulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1386.]).

[Scheme 1]

Experimental

Crystal data

  • C14H15ClO2S

  • Mr = 282.77

  • Triclinic, [P \overline 1]

  • a = 6.3337 (3) Å

  • b = 8.9449 (4) Å

  • c = 12.1157 (5) Å

  • α = 73.614 (2)°

  • β = 78.110 (2)°

  • γ = 88.087 (2)°

  • V = 644.17 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 173 K

  • 0.35 × 0.26 × 0.20 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 = 0.858, Tmax = 0.916

  • 11628 measured reflections

  • 2995 independent reflections

  • 2514 reflections with I > 2σ(I)

  • Rint = 0.055
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.105

  • S = 1.05

  • 2995 reflections

  • 164 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯O2i 0.95 2.61 3.349 (2) 135
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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019775/zl2373sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019775/zl2373Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019775/zl2373Isup3.cml

checkCIF report


Comment top

Recently, many compounds involving a benzofuran ring system have drawn much attention due to their inetresting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As part of our ongoing project of the substituent effect on the solid state structures of 3-cyclopentylsulfinyl-5-halo-2-methyl-1-benzofuran analogues (Seo et al., 2011), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring is in the envelope form. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a benzene H atom and the O atom of the sulfinyl group (Table 1; C5—H5···O2i). The crystal packing (Fig. 2) is further stabilized by a weak slipped π–π interaction between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2ii distance of 3.784 (3) Å and an interplanar distance of 3.199 (3) Å resulting in a slippage of 2.021 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For a structural study of the related compound, 5-bromo-3-cyclopentylsulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011).

Experimental top

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclopentylsulfanyl-2-methy1-benzofuran (293 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 386–387 K; Rf = 0.48 (hexane–ethyl acetate, 1:1 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, 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 the atom numbering scheme. Displacement ellipsoids are 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 π–π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x, y - 1, z ; (ii) - x + 1, - y, - z + 1; (iii) x, y + 1, z; (iv) - x + 1, - y + 1, - z + 1.]
5-Chloro-3-cyclopentylsulfinyl-2-methyl-1-benzofuran top
Crystal data top
C14H15ClO2SZ = 2
Mr = 282.77F(000) = 296
Triclinic, P1Dx = 1.458 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3337 (3) ÅCell parameters from 4102 reflections
b = 8.9449 (4) Åθ = 2.4–27.6°
c = 12.1157 (5) ŵ = 0.45 mm−1
α = 73.614 (2)°T = 173 K
β = 78.110 (2)°Block, colourless
γ = 88.087 (2)°0.35 × 0.26 × 0.20 mm
V = 644.17 (5) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		2995 independent reflections
Radiation source: rotating anode2514 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.055
Detector resolution: 10.0 pixels mm-1θmax = 27.7°, θmin = 1.8°
ϕ and ω scansh = −8→8
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −11→11
Tmin = 0.858, Tmax = 0.916l = −15→14
11628 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)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.105H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.2468P]
where P = (Fo2 + 2Fc2)/3
2995 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C14H15ClO2Sγ = 88.087 (2)°
Mr = 282.77V = 644.17 (5) Å3
Triclinic, P1Z = 2
a = 6.3337 (3) ÅMo Kα radiation
b = 8.9449 (4) ŵ = 0.45 mm−1
c = 12.1157 (5) ÅT = 173 K
α = 73.614 (2)°0.35 × 0.26 × 0.20 mm
β = 78.110 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		2995 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2514 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 0.916Rint = 0.055
11628 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.05Δρmax = 0.43 e Å−3
2995 reflectionsΔρmin = −0.26 e Å−3
164 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
Cl11.11290 (7)0.07397 (6)0.16222 (5)0.03628 (15)
S10.45480 (7)0.51787 (5)0.33115 (4)0.02483 (14)
O10.24300 (19)0.08162 (14)0.43094 (11)0.0254 (3)
O20.6818 (2)0.54497 (15)0.33897 (13)0.0345 (3)
C10.4123 (3)0.3158 (2)0.36271 (16)0.0238 (4)
C20.5584 (3)0.2048 (2)0.32358 (15)0.0216 (4)
C30.7684 (3)0.2107 (2)0.25933 (16)0.0238 (4)
H30.85120.30540.22870.029*
C40.8508 (3)0.0724 (2)0.24220 (16)0.0247 (4)
C50.7343 (3)−0.0685 (2)0.28622 (17)0.0267 (4)
H50.7976−0.16060.27140.032*
C60.5269 (3)−0.0747 (2)0.35141 (17)0.0263 (4)
H60.4450−0.16970.38330.032*
C70.4445 (3)0.0636 (2)0.36806 (15)0.0224 (4)
C80.2289 (3)0.2361 (2)0.42738 (16)0.0246 (4)
C90.0257 (3)0.2831 (2)0.49225 (18)0.0313 (4)
H9A0.05740.36300.52810.047*
H9B−0.04430.19210.55390.047*
H9C−0.07070.32520.43780.047*
C100.4471 (3)0.5660 (2)0.17647 (16)0.0252 (4)
H100.55790.50560.13660.030*
C110.4876 (3)0.7408 (2)0.11699 (17)0.0305 (4)
H11A0.42440.80300.17100.037*
H11B0.64400.76650.08940.037*
C120.3739 (3)0.7690 (2)0.01427 (18)0.0343 (4)
H12A0.34330.8808−0.01550.041*
H12B0.46190.7336−0.05080.041*
C130.1660 (3)0.6720 (3)0.0669 (2)0.0414 (5)
H13A0.11290.63970.00550.050*
H13B0.05280.73240.10350.050*
C140.2223 (3)0.5299 (2)0.15928 (19)0.0335 (4)
H14A0.22500.43540.13190.040*
H14B0.11500.51260.23400.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0254 (2)0.0385 (3)0.0432 (3)0.00585 (19)−0.0012 (2)−0.0135 (2)
S10.0279 (2)0.0181 (2)0.0302 (3)0.00119 (17)−0.00814 (18)−0.00808 (18)
O10.0235 (6)0.0213 (6)0.0307 (7)−0.0011 (5)−0.0035 (5)−0.0077 (5)
O20.0342 (7)0.0262 (7)0.0469 (9)−0.0037 (6)−0.0199 (6)−0.0076 (6)
C10.0257 (8)0.0194 (8)0.0273 (10)0.0016 (7)−0.0076 (7)−0.0069 (7)
C20.0236 (8)0.0205 (8)0.0230 (9)0.0018 (6)−0.0085 (7)−0.0070 (7)
C30.0240 (8)0.0219 (9)0.0264 (9)0.0000 (7)−0.0070 (7)−0.0068 (7)
C40.0217 (8)0.0286 (9)0.0252 (9)0.0041 (7)−0.0075 (7)−0.0084 (8)
C50.0318 (9)0.0228 (9)0.0298 (10)0.0052 (7)−0.0114 (8)−0.0110 (8)
C60.0293 (9)0.0210 (9)0.0297 (10)−0.0024 (7)−0.0082 (7)−0.0071 (8)
C70.0222 (8)0.0225 (9)0.0226 (9)−0.0009 (6)−0.0063 (7)−0.0053 (7)
C80.0259 (9)0.0219 (9)0.0268 (10)0.0010 (7)−0.0071 (7)−0.0069 (7)
C90.0264 (9)0.0296 (10)0.0350 (11)0.0027 (8)−0.0020 (8)−0.0079 (9)
C100.0249 (9)0.0228 (9)0.0289 (10)0.0010 (7)−0.0063 (7)−0.0084 (8)
C110.0346 (10)0.0234 (10)0.0325 (11)−0.0034 (8)−0.0108 (8)−0.0031 (8)
C120.0390 (11)0.0325 (11)0.0315 (11)0.0022 (8)−0.0120 (9)−0.0058 (9)
C130.0331 (11)0.0504 (14)0.0406 (13)0.0013 (9)−0.0149 (9)−0.0074 (11)
C140.0294 (10)0.0325 (11)0.0404 (12)−0.0035 (8)−0.0123 (8)−0.0087 (9)
Geometric parameters (Å, º) top
Cl1—C41.7398 (18)C9—H9A0.9800
S1—O21.4926 (13)C9—H9B0.9800
S1—C11.7571 (17)C9—H9C0.9800
S1—C101.8113 (19)C10—C111.532 (2)
O1—C81.371 (2)C10—C141.538 (2)
O1—C71.375 (2)C10—H101.0000
C1—C81.355 (3)C11—C121.520 (3)
C1—C21.446 (2)C11—H11A0.9900
C2—C71.387 (2)C11—H11B0.9900
C2—C31.390 (2)C12—C131.520 (3)
C3—C41.380 (2)C12—H12A0.9900
C3—H30.9500C12—H12B0.9900
C4—C51.392 (3)C13—C141.525 (3)
C5—C61.380 (3)C13—H13A0.9900
C5—H50.9500C13—H13B0.9900
C6—C71.377 (2)C14—H14A0.9900
C6—H60.9500C14—H14B0.9900
C8—C91.478 (3)
O2—S1—C1107.59 (8)H9A—C9—H9C109.5
O2—S1—C10107.13 (8)H9B—C9—H9C109.5
C1—S1—C1096.85 (8)C11—C10—C14105.36 (15)
C8—O1—C7106.57 (13)C11—C10—S1111.26 (12)
C8—C1—C2107.35 (15)C14—C10—S1111.01 (13)
C8—C1—S1125.01 (14)C11—C10—H10109.7
C2—C1—S1127.63 (14)C14—C10—H10109.7
C7—C2—C3119.67 (16)S1—C10—H10109.7
C7—C2—C1104.65 (15)C12—C11—C10102.68 (15)
C3—C2—C1135.66 (16)C12—C11—H11A111.2
C4—C3—C2116.77 (16)C10—C11—H11A111.2
C4—C3—H3121.6C12—C11—H11B111.2
C2—C3—H3121.6C10—C11—H11B111.2
C3—C4—C5123.11 (17)H11A—C11—H11B109.1
C3—C4—Cl1118.46 (14)C13—C12—C11103.48 (17)
C5—C4—Cl1118.43 (14)C13—C12—H12A111.1
C6—C5—C4120.05 (17)C11—C12—H12A111.1
C6—C5—H5120.0C13—C12—H12B111.1
C4—C5—H5120.0C11—C12—H12B111.1
C7—C6—C5116.80 (16)H12A—C12—H12B109.0
C7—C6—H6121.6C12—C13—C14105.84 (16)
C5—C6—H6121.6C12—C13—H13A110.6
O1—C7—C6125.67 (16)C14—C13—H13A110.6
O1—C7—C2110.74 (15)C12—C13—H13B110.6
C6—C7—C2123.59 (17)C14—C13—H13B110.6
C1—C8—O1110.68 (15)H13A—C13—H13B108.7
C1—C8—C9132.96 (17)C13—C14—C10105.96 (16)
O1—C8—C9116.36 (15)C13—C14—H14A110.5
C8—C9—H9A109.5C10—C14—H14A110.5
C8—C9—H9B109.5C13—C14—H14B110.5
H9A—C9—H9B109.5C10—C14—H14B110.5
C8—C9—H9C109.5H14A—C14—H14B108.7
O2—S1—C1—C8140.45 (16)C1—C2—C7—O1−0.31 (19)
C10—S1—C1—C8−109.10 (16)C3—C2—C7—C6−0.7 (3)
O2—S1—C1—C2−41.40 (18)C1—C2—C7—C6−179.57 (16)
C10—S1—C1—C269.05 (16)C2—C1—C8—O1−1.41 (19)
C8—C1—C2—C71.03 (19)S1—C1—C8—O1177.05 (12)
S1—C1—C2—C7−177.38 (13)C2—C1—C8—C9178.34 (19)
C8—C1—C2—C3−177.56 (19)S1—C1—C8—C9−3.2 (3)
S1—C1—C2—C34.0 (3)C7—O1—C8—C11.22 (18)
C7—C2—C3—C40.9 (2)C7—O1—C8—C9−178.58 (15)
C1—C2—C3—C4179.35 (18)O2—S1—C10—C11−67.30 (14)
C2—C3—C4—C5−0.3 (3)C1—S1—C10—C11−178.13 (13)
C2—C3—C4—Cl1179.95 (12)O2—S1—C10—C14175.72 (12)
C3—C4—C5—C6−0.7 (3)C1—S1—C10—C1464.89 (14)
Cl1—C4—C5—C6179.13 (13)C14—C10—C11—C12−33.7 (2)
C4—C5—C6—C70.9 (3)S1—C10—C11—C12−154.09 (13)
C8—O1—C7—C6178.72 (16)C10—C11—C12—C1341.2 (2)
C8—O1—C7—C2−0.52 (18)C11—C12—C13—C14−33.2 (2)
C5—C6—C7—O1−179.37 (15)C12—C13—C14—C1012.1 (2)
C5—C6—C7—C2−0.2 (3)C11—C10—C14—C1313.5 (2)
C3—C2—C7—O1178.56 (14)S1—C10—C14—C13134.01 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.952.613.349 (2)135
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC14H15ClO2S
Mr282.77
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.3337 (3), 8.9449 (4), 12.1157 (5)
α, β, γ (°)73.614 (2), 78.110 (2), 88.087 (2)
V (Å3)644.17 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.35 × 0.26 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.858, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections		11628, 2995, 2514
Rint0.055
(sin θ/λ)max (Å−1)0.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.105, 1.05
No. of reflections2995
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.43, −0.26

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···O2i0.952.613.349 (2)135
Symmetry code: (i) x, y−1, z.
 

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ISSN: 2056-9890
Volume 67| Part 7| July 2011| Page o1557
doi:10.1107/S1600536811019775
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