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Acta Cryst. (2011). E67, o1226    [ doi:10.1107/S1600536811014784 ]

3-(4-Chlorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran

H. D. Choi, P. J. Seo and U. Lee

Abstract top

In the title molecule, C18H17ClO3S, the 4-chlorophenyl ring makes a dihedral angle of 77.03 (5)° with the mean plane of the benzofuran fragment. In the crystal structure, the molecules are linked by weak intermolecular C-H...O hydrogen bonds and C-H...[pi] interactions

Comment top

Many compounds containing a benzofuran ring have recently drawn considerable attention due to their interesting 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 compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing program of the substituent effect on the solid state structures of 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran analogues (Choi et al., 2008, 2010), 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 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-chlorophenyl ring and the mean plane of the benzofuran fragment is 77.03 (5)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a methyl H atom and the O atom of the sulfonyl group (Table 1; C12—H12C···O3i). The crystal packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions between a methyl H atom of the isopropyl group and the benzene ring of an adjacent molecule (Table 1; C10—H11B···Cgii, Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the pharmacological 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 the structures of related 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008, 2010).

Experimental top

77% 3-chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-5-isopropyl-2-methyl-1-benzofuran (380 mg, 1.2 mmol) in dichloromethane (40 ml) at 273 K. After being stirred at room temperature for 6 h, 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 (benzene) to afford the title compound as a colourless solid [yield 71%, m.p. 409–410 K; Rf = 0.65 (benzene)]. 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: C—H = 0.93 Å for aryl, 0.98 Å for methine, and 0.96 Å for methyl H atoms, with Uiso(H) = 1.2Ueq(C) for aryl and methine, 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 along the a axis of the C—H···O interactions (dotted lines) in the crystal structure of the title compound. [See Table 1 for details; Symmetry codes: (i) x, -y + 1/2, z + 1/2; (iii) x, -y + 1/2, z - 1/2]
[Figure 3] Fig. 3. A view along the c axis of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. [See Table 1 for details; Symmetry codes: (ii) - x + 1, y -1/2, - z + 1/2; (iv) -x + 1, y + 1/2, -z + 1/2]
3-(4-Chlorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran top
Crystal data top
C18H17ClO3SF(000) = 728
Mr = 348.83Dx = 1.392 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5946 reflections
a = 11.4851 (4) Åθ = 2.4–28.3°
b = 11.3194 (4) ŵ = 0.37 mm−1
c = 13.0600 (4) ÅT = 296 K
β = 101.475 (2)°Block, colourless
V = 1663.92 (10) Å30.29 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer		3643 independent reflections
Radiation source: rotating anode3109 reflections with I > 2σ(I)
graphite multilayerRint = 0.040
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.8°
φ and ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −14→14
Tmin = 0.660, Tmax = 0.746l = −16→16
14572 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) = 0.120H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.8346P]
where P = (Fo2 + 2Fc2)/3
3643 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.67 e Å−3
1 restraintΔρmin = −0.65 e Å−3
Crystal data top
C18H17ClO3SV = 1663.92 (10) Å3
Mr = 348.83Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.4851 (4) ŵ = 0.37 mm−1
b = 11.3194 (4) ÅT = 296 K
c = 13.0600 (4) Å0.29 × 0.20 × 0.18 mm
β = 101.475 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3643 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3109 reflections with I > 2σ(I)
Tmin = 0.660, Tmax = 0.746Rint = 0.040
14572 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.120Δρmax = 0.67 e Å−3
S = 1.08Δρmin = −0.65 e Å−3
3643 reflectionsAbsolute structure: ?
211 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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
Cl10.26041 (5)0.75171 (5)−0.02985 (5)0.04730 (19)
S10.05170 (4)0.34612 (5)0.20282 (4)0.02918 (16)
O10.28084 (13)0.32071 (12)0.46858 (10)0.0284 (3)
O2−0.04776 (13)0.39127 (15)0.24196 (13)0.0410 (4)
O30.03725 (14)0.24367 (13)0.13660 (12)0.0364 (4)
C10.16557 (17)0.31448 (17)0.30843 (15)0.0259 (4)
C20.26193 (16)0.23122 (16)0.30977 (14)0.0234 (4)
C30.29613 (17)0.15214 (17)0.23947 (15)0.0267 (4)
H30.25210.14540.17180.032*
C40.39669 (18)0.08375 (18)0.27190 (15)0.0276 (4)
C50.46245 (17)0.09257 (17)0.37270 (14)0.0290 (4)
H50.52920.04520.39300.035*
C60.42883 (17)0.17475 (17)0.44745 (14)0.0279 (4)
H60.47200.18270.51530.033*
C70.32941 (17)0.23906 (16)0.41025 (14)0.0242 (4)
C80.18122 (18)0.36468 (18)0.40469 (16)0.0287 (4)
C90.4355 (2)−0.0030 (2)0.19646 (17)0.0356 (5)
H90.3747−0.00180.13210.043*
C100.5518 (3)0.0338 (3)0.1676 (3)0.0635 (8)
H10A0.54440.11240.13950.095*
H10B0.5708−0.01970.11630.095*
H10C0.61400.03200.22880.095*
C110.4420 (3)−0.1283 (2)0.2381 (2)0.0586 (8)
H11A0.5058−0.13440.29780.088*
H11B0.4560−0.18180.18480.088*
H11C0.3684−0.14820.25810.088*
C120.1135 (2)0.4515 (2)0.45385 (18)0.0420 (6)
H12A0.05300.48650.40130.063*
H12B0.16620.51190.48740.063*
H12C0.07720.41240.50480.063*
C130.10801 (17)0.46178 (18)0.13593 (16)0.0289 (4)
C140.1036 (2)0.5775 (2)0.17029 (17)0.0358 (5)
H140.06930.59440.22740.043*
C150.1502 (2)0.6673 (2)0.11922 (19)0.0383 (5)
H150.14840.74500.14190.046*
C160.19963 (18)0.6399 (2)0.03376 (18)0.0339 (5)
C170.2032 (2)0.5257 (2)−0.00179 (18)0.0368 (5)
H170.23630.5092−0.05970.044*
C180.15686 (19)0.4358 (2)0.04978 (16)0.0336 (5)
H180.15850.35830.02670.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0377 (3)0.0432 (4)0.0619 (4)−0.0010 (2)0.0123 (3)0.0175 (3)
S10.0243 (3)0.0286 (3)0.0343 (3)0.00487 (19)0.0049 (2)0.0052 (2)
O10.0352 (7)0.0273 (7)0.0242 (7)0.0024 (6)0.0093 (6)−0.0011 (5)
O20.0282 (8)0.0458 (10)0.0512 (9)0.0108 (7)0.0136 (7)0.0117 (8)
O30.0346 (8)0.0310 (8)0.0399 (8)0.0000 (6)−0.0015 (7)−0.0003 (6)
C10.0260 (9)0.0242 (9)0.0283 (9)0.0041 (7)0.0076 (7)0.0036 (8)
C20.0235 (9)0.0224 (9)0.0247 (9)0.0009 (7)0.0057 (7)0.0031 (7)
C30.0297 (10)0.0274 (10)0.0222 (9)0.0030 (8)0.0034 (8)−0.0001 (7)
C40.0303 (10)0.0250 (10)0.0288 (9)0.0043 (8)0.0092 (8)0.0019 (8)
C50.0251 (9)0.0283 (11)0.0336 (10)0.0041 (8)0.0056 (8)0.0052 (8)
C60.0281 (9)0.0292 (10)0.0246 (9)−0.0026 (8)0.0012 (8)0.0031 (8)
C70.0282 (9)0.0221 (9)0.0238 (9)−0.0024 (7)0.0090 (7)0.0014 (7)
C80.0327 (10)0.0245 (10)0.0319 (10)0.0034 (8)0.0133 (8)0.0041 (8)
C90.0426 (12)0.0338 (12)0.0312 (10)0.0136 (9)0.0095 (9)−0.0016 (9)
C100.073 (2)0.0551 (18)0.077 (2)0.0068 (14)0.0497 (17)−0.0074 (15)
C110.096 (2)0.0326 (13)0.0543 (16)0.0061 (14)0.0326 (16)−0.0058 (11)
C120.0532 (14)0.0375 (13)0.0400 (12)0.0143 (11)0.0209 (11)−0.0020 (10)
C130.0253 (9)0.0287 (10)0.0321 (10)0.0072 (8)0.0041 (8)0.0051 (8)
C140.0398 (11)0.0320 (12)0.0373 (11)0.0078 (9)0.0117 (9)0.0019 (9)
C150.0431 (12)0.0269 (11)0.0455 (12)0.0044 (9)0.0101 (10)−0.0010 (9)
C160.0254 (10)0.0342 (12)0.0412 (12)0.0041 (8)0.0045 (8)0.0100 (9)
C170.0351 (11)0.0397 (13)0.0384 (11)0.0087 (9)0.0141 (9)0.0055 (9)
C180.0355 (11)0.0306 (11)0.0354 (11)0.0091 (9)0.0086 (9)0.0017 (9)
Geometric parameters (Å, °) top
Cl1—C161.735 (2)C9—C101.517 (4)
S1—O21.4352 (15)C9—H90.9800
S1—O31.4364 (16)C10—H10A0.9600
S1—C11.739 (2)C10—H10B0.9600
S1—C131.766 (2)C10—H10C0.9600
O1—C81.369 (2)C11—H11A0.9600
O1—C71.384 (2)C11—H11B0.9600
C1—C81.359 (3)C11—H11C0.9600
C1—C21.451 (3)C12—H12A0.9600
C2—C71.388 (3)C12—H12B0.9600
C2—C31.394 (3)C12—H12C0.9600
C3—C41.385 (3)C13—C181.385 (3)
C3—H30.9300C13—C141.388 (3)
C4—C51.385 (3)C14—C151.381 (3)
C4—C91.519 (3)C14—H140.9300
C5—C61.4551 (17)C15—C161.384 (3)
C5—H50.9300C15—H150.9300
C6—C71.360 (3)C16—C171.377 (3)
C6—H60.9300C17—C181.383 (3)
C8—C121.477 (3)C17—H170.9300
C9—C111.516 (3)C18—H180.9300
O2—S1—O3119.81 (10)C9—C10—H10A109.5
O2—S1—C1108.49 (9)C9—C10—H10B109.5
O3—S1—C1106.86 (9)H10A—C10—H10B109.5
O2—S1—C13107.93 (9)C9—C10—H10C109.5
O3—S1—C13108.09 (10)H10A—C10—H10C109.5
C1—S1—C13104.68 (9)H10B—C10—H10C109.5
C8—O1—C7106.68 (15)C9—C11—H11A109.5
C8—C1—C2107.47 (17)C9—C11—H11B109.5
C8—C1—S1126.02 (15)H11A—C11—H11B109.5
C2—C1—S1126.50 (15)C9—C11—H11C109.5
C7—C2—C3119.10 (17)H11A—C11—H11C109.5
C7—C2—C1104.54 (16)H11B—C11—H11C109.5
C3—C2—C1136.35 (18)C8—C12—H12A109.5
C4—C3—C2119.01 (18)C8—C12—H12B109.5
C4—C3—H3120.5H12A—C12—H12B109.5
C2—C3—H3120.5C8—C12—H12C109.5
C3—C4—C5120.95 (17)H12A—C12—H12C109.5
C3—C4—C9119.83 (18)H12B—C12—H12C109.5
C5—C4—C9119.22 (17)C18—C13—C14120.6 (2)
C4—C5—C6121.10 (17)C18—C13—S1119.47 (17)
C4—C5—H5119.4C14—C13—S1119.90 (16)
C6—C5—H5119.4C15—C14—C13119.7 (2)
C7—C6—C5114.74 (17)C15—C14—H14120.1
C7—C6—H6122.6C13—C14—H14120.1
C5—C6—H6122.6C14—C15—C16119.0 (2)
C6—C7—O1124.24 (17)C14—C15—H15120.5
C6—C7—C2125.10 (17)C16—C15—H15120.5
O1—C7—C2110.65 (16)C17—C16—C15121.8 (2)
C1—C8—O1110.66 (17)C17—C16—Cl1118.80 (17)
C1—C8—C12134.1 (2)C15—C16—Cl1119.43 (18)
O1—C8—C12115.19 (18)C16—C17—C18119.1 (2)
C11—C9—C10111.3 (2)C16—C17—H17120.5
C11—C9—C4111.85 (18)C18—C17—H17120.5
C10—C9—C4111.7 (2)C17—C18—C13119.8 (2)
C11—C9—H9107.2C17—C18—H18120.1
C10—C9—H9107.2C13—C18—H18120.1
C4—C9—H9107.2
O2—S1—C1—C8−24.7 (2)S1—C1—C8—O1−179.01 (14)
O3—S1—C1—C8−155.17 (18)C2—C1—C8—C12−177.8 (2)
C13—S1—C1—C890.33 (19)S1—C1—C8—C123.0 (4)
O2—S1—C1—C2156.20 (17)C7—O1—C8—C1−0.3 (2)
O3—S1—C1—C225.73 (19)C7—O1—C8—C12178.10 (17)
C13—S1—C1—C2−88.77 (18)C3—C4—C9—C11−122.0 (2)
C8—C1—C2—C70.0 (2)C5—C4—C9—C1157.6 (3)
S1—C1—C2—C7179.20 (14)C3—C4—C9—C10112.5 (2)
C8—C1—C2—C3178.7 (2)C5—C4—C9—C10−67.9 (3)
S1—C1—C2—C3−2.0 (3)O2—S1—C13—C18−146.81 (17)
C7—C2—C3—C4−0.1 (3)O3—S1—C13—C18−15.87 (19)
C1—C2—C3—C4−178.8 (2)C1—S1—C13—C1897.77 (18)
C2—C3—C4—C50.4 (3)O2—S1—C13—C1433.5 (2)
C2—C3—C4—C9−179.98 (18)O3—S1—C13—C14164.47 (17)
C3—C4—C5—C6−0.6 (3)C1—S1—C13—C14−81.89 (18)
C9—C4—C5—C6179.76 (18)C18—C13—C14—C15−1.2 (3)
C4—C5—C6—C70.5 (3)S1—C13—C14—C15178.50 (17)
C5—C6—C7—O1178.91 (16)C13—C14—C15—C160.6 (3)
C5—C6—C7—C2−0.2 (3)C14—C15—C16—C170.2 (3)
C8—O1—C7—C6−178.93 (18)C14—C15—C16—Cl1−179.07 (17)
C8—O1—C7—C20.3 (2)C15—C16—C17—C18−0.5 (3)
C3—C2—C7—C60.0 (3)Cl1—C16—C17—C18178.81 (17)
C1—C2—C7—C6179.07 (18)C16—C17—C18—C13−0.1 (3)
C3—C2—C7—O1−179.21 (16)C14—C13—C18—C170.9 (3)
C1—C2—C7—O1−0.2 (2)S1—C13—C18—C17−178.76 (16)
C2—C1—C8—O10.2 (2)
Hydrogen-bond geometry (Å, °) top
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C12—H12C···O3i0.962.573.489 (3)160
C11—H11B···Cgii0.962.813.562 (3)136
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C12—H12C···O3i0.962.573.489 (3)160
C11—H11B···Cgii0.962.813.562 (3)136
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2.
Acknowledgements top

This work was supported by a Dong-eui University Foundation Grant (2011).

references
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