5-Chloro-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

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

doi:10.1107/S1600536813018400

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1213

doi:10.1107/S1600536813018400

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5-Chloro-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a and Uk Lee ^b ^*

^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 June 2013; accepted 3 July 2013; online 6 July 2013)

In the title compound, C₁₆H₁₃ClO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.004 (2) Å] of the benzofuran ring system and the 4-methylphenyl ring is 29.25 (8)°. In the crystal, inversion dimers linked by pairs of weak C—H⋯O interactions generate R₂²(14) loops.

Related literature

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 crystal structures of related compounds, see: Choi et al. (2007 , 2009 ).

Experimental

Crystal data

C₁₆H₁₃ClO₂S
M_r = 304.77
Triclinic, $[P \overline 1]$
a = 8.0694 (8) Å
b = 8.0763 (8) Å
c = 11.4208 (11) Å
α = 90.185 (6)°
β = 96.280 (6)°
γ = 111.701 (6)°
V = 686.63 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 173 K
0.35 × 0.34 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.865, T_max = 0.958
12808 measured reflections
3423 independent reflections
3021 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.05
3423 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2ⁱ	0.95	2.54	3.436 (2)	158
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018400/nk2211sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018400/nk2211Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018400/nk2211Isup3.cml

checkCIF report

Comment top

Many compounds having a benzofuran moiety have drawn much attention due to their valuable 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 a part of our continuing study of 5-chloro-3-methylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2007) and 4-fluorophenyl (Choi et al., 2009) substituents in 2-position, 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 0.004 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the mean plane of the benzofuran ring system and the 4-methylphenyl ring is 29.25 (8)°. In the crystal structure, molecules are connected by weak C—H···O hydrogen bonds (Table 1), resulting in a three-dimensional network.

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 crystal structures of related compounds, see: Choi et al. (2007, 2009).

Experimental top

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-chloro-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (317 mg, 1.1 mmol) in dichloromethane (40 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 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 70%, m.p. 459–460 K; R_f = 0.49 (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 acetone at room temperature.

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. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

5-Chloro-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₆H₁₃ClO₂S	Z = 2
M_r = 304.77	F(000) = 316
Triclinic, P1	D_x = 1.474 Mg m⁻³
Hall symbol: -P 1	Melting point = 459–460 K
a = 8.0694 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0763 (8) Å	Cell parameters from 4424 reflections
c = 11.4208 (11) Å	θ = 2.7–28.1°
α = 90.185 (6)°	µ = 0.43 mm⁻¹
β = 96.280 (6)°	T = 173 K
γ = 111.701 (6)°	Block, colourless
V = 686.63 (12) Å³	0.35 × 0.34 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3423 independent reflections
Radiation source: rotating anode	3021 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.048
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.8°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.865, T_max = 0.958	l = −15→15
12808 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0432P)² + 0.3137P] where P = (F_o² + 2F_c²)/3
3423 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₃ClO₂S	γ = 111.701 (6)°
M_r = 304.77	V = 686.63 (12) Å³
Triclinic, P1	Z = 2
a = 8.0694 (8) Å	Mo Kα radiation
b = 8.0763 (8) Å	µ = 0.43 mm⁻¹
c = 11.4208 (11) Å	T = 173 K
α = 90.185 (6)°	0.35 × 0.34 × 0.10 mm
β = 96.280 (6)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3423 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3021 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.958	R_int = 0.048
12808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
3423 reflections	Δρ_min = −0.28 e Å⁻³
183 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

	x	y	z	U_iso*/U_eq
Cl1	0.21613 (6)	−0.06293 (6)	0.00434 (4)	0.03430 (13)
S1	0.79728 (5)	0.32171 (5)	0.40498 (4)	0.02612 (12)
O1	0.30621 (15)	0.15287 (15)	0.50057 (10)	0.0257 (2)
O2	0.82257 (18)	0.19866 (17)	0.31756 (13)	0.0401 (3)
C1	0.5655 (2)	0.2423 (2)	0.41897 (14)	0.0239 (3)
C2	0.4219 (2)	0.1456 (2)	0.32835 (14)	0.0236 (3)
C3	0.4092 (2)	0.0990 (2)	0.20888 (14)	0.0259 (3)
H3	0.5122	0.1328	0.1679	0.031*
C4	0.2396 (2)	0.0014 (2)	0.15325 (14)	0.0269 (3)
C5	0.0852 (2)	−0.0505 (2)	0.21040 (15)	0.0291 (3)
H5	−0.0284	−0.1179	0.1680	0.035*
C6	0.0970 (2)	−0.0040 (2)	0.32891 (15)	0.0282 (3)
H6	−0.0061	−0.0370	0.3698	0.034*
C7	0.2666 (2)	0.0929 (2)	0.38407 (14)	0.0241 (3)
C8	0.4897 (2)	0.2427 (2)	0.52001 (14)	0.0238 (3)
C9	0.5607 (2)	0.3179 (2)	0.63960 (14)	0.0238 (3)
C10	0.7141 (2)	0.4725 (2)	0.66158 (15)	0.0280 (3)
H10	0.7738	0.5314	0.5976	0.034*
C11	0.7804 (2)	0.5414 (2)	0.77602 (15)	0.0296 (4)
H11	0.8862	0.6458	0.7898	0.036*
C12	0.6930 (2)	0.4586 (2)	0.87084 (15)	0.0282 (3)
C13	0.5390 (2)	0.3061 (2)	0.84809 (15)	0.0281 (3)
H13	0.4780	0.2489	0.9121	0.034*
C14	0.4720 (2)	0.2353 (2)	0.73466 (14)	0.0256 (3)
H14	0.3661	0.1309	0.7213	0.031*
C15	0.7646 (3)	0.5323 (3)	0.99514 (16)	0.0390 (4)
H15A	0.6653	0.5005	1.0436	0.059*
H15B	0.8228	0.6624	0.9952	0.059*
H15C	0.8522	0.4818	1.0276	0.059*
C16	0.8112 (3)	0.5192 (2)	0.32875 (16)	0.0318 (4)
H16A	0.9311	0.5749	0.3036	0.048*
H16B	0.7896	0.6031	0.3815	0.048*
H16C	0.7206	0.4877	0.2595	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0365 (3)	0.0364 (2)	0.0259 (2)	0.01030 (19)	−0.00156 (17)	−0.00172 (16)
S1	0.0199 (2)	0.0253 (2)	0.0326 (2)	0.00772 (16)	0.00336 (15)	0.00359 (15)
O1	0.0207 (6)	0.0284 (6)	0.0265 (6)	0.0073 (5)	0.0031 (4)	−0.0001 (4)
O2	0.0316 (7)	0.0302 (6)	0.0614 (9)	0.0115 (6)	0.0178 (6)	−0.0034 (6)
C1	0.0214 (8)	0.0241 (7)	0.0262 (7)	0.0090 (6)	0.0017 (6)	0.0007 (6)
C2	0.0218 (8)	0.0215 (7)	0.0281 (8)	0.0091 (6)	0.0014 (6)	0.0021 (6)
C3	0.0257 (8)	0.0260 (7)	0.0269 (8)	0.0107 (6)	0.0035 (6)	0.0021 (6)
C4	0.0303 (9)	0.0243 (7)	0.0255 (7)	0.0106 (7)	−0.0008 (6)	0.0001 (6)
C5	0.0252 (8)	0.0272 (8)	0.0315 (8)	0.0076 (7)	−0.0026 (7)	0.0006 (6)
C6	0.0226 (8)	0.0287 (8)	0.0329 (8)	0.0089 (7)	0.0031 (6)	0.0024 (6)
C7	0.0238 (8)	0.0237 (7)	0.0256 (7)	0.0098 (6)	0.0021 (6)	0.0015 (6)
C8	0.0201 (8)	0.0218 (7)	0.0290 (8)	0.0073 (6)	0.0021 (6)	0.0021 (6)
C9	0.0241 (8)	0.0240 (7)	0.0258 (7)	0.0117 (6)	0.0034 (6)	0.0014 (6)
C10	0.0301 (9)	0.0248 (7)	0.0282 (8)	0.0081 (7)	0.0072 (7)	0.0031 (6)
C11	0.0297 (9)	0.0234 (7)	0.0329 (8)	0.0065 (7)	0.0046 (7)	−0.0028 (6)
C12	0.0311 (9)	0.0278 (8)	0.0275 (8)	0.0132 (7)	0.0030 (7)	−0.0024 (6)
C13	0.0298 (9)	0.0296 (8)	0.0270 (8)	0.0123 (7)	0.0075 (7)	0.0048 (6)
C14	0.0228 (8)	0.0236 (7)	0.0301 (8)	0.0081 (6)	0.0040 (6)	0.0027 (6)
C15	0.0417 (11)	0.0422 (10)	0.0295 (9)	0.0116 (9)	0.0035 (8)	−0.0084 (7)
C16	0.0342 (10)	0.0272 (8)	0.0355 (9)	0.0118 (7)	0.0087 (7)	0.0073 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7462 (16)	C9—C10	1.393 (2)
S1—O2	1.4879 (13)	C9—C14	1.399 (2)
S1—C1	1.7648 (17)	C10—C11	1.388 (2)
S1—C16	1.7925 (17)	C10—H10	0.9500
O1—C7	1.3768 (18)	C11—C12	1.393 (2)
O1—C8	1.3790 (19)	C11—H11	0.9500
C1—C8	1.364 (2)	C12—C13	1.387 (2)
C1—C2	1.445 (2)	C12—C15	1.505 (2)
C2—C7	1.393 (2)	C13—C14	1.382 (2)
C2—C3	1.397 (2)	C13—H13	0.9500
C3—C4	1.381 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.396 (2)	C15—H15B	0.9800
C5—C6	1.387 (2)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.378 (2)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C8—C9	1.459 (2)

O2—S1—C1	106.64 (7)	C10—C9—C8	121.45 (14)
O2—S1—C16	106.07 (8)	C14—C9—C8	119.67 (15)
C1—S1—C16	97.73 (8)	C11—C10—C9	120.65 (15)
C7—O1—C8	106.62 (12)	C11—C10—H10	119.7
C8—C1—C2	107.24 (14)	C9—C10—H10	119.7
C8—C1—S1	126.49 (13)	C10—C11—C12	120.54 (16)
C2—C1—S1	125.89 (12)	C10—C11—H11	119.7
C7—C2—C3	119.27 (15)	C12—C11—H11	119.7
C7—C2—C1	105.00 (14)	C13—C12—C11	118.46 (15)
C3—C2—C1	135.73 (15)	C13—C12—C15	120.74 (16)
C4—C3—C2	116.75 (15)	C11—C12—C15	120.80 (16)
C4—C3—H3	121.6	C14—C13—C12	121.65 (16)
C2—C3—H3	121.6	C14—C13—H13	119.2
C3—C4—C5	123.29 (15)	C12—C13—H13	119.2
C3—C4—Cl1	118.71 (13)	C13—C14—C9	119.81 (15)
C5—C4—Cl1	118.00 (13)	C13—C14—H14	120.1
C6—C5—C4	120.20 (15)	C9—C14—H14	120.1
C6—C5—H5	119.9	C12—C15—H15A	109.5
C4—C5—H5	119.9	C12—C15—H15B	109.5
C7—C6—C5	116.26 (15)	H15A—C15—H15B	109.5
C7—C6—H6	121.9	C12—C15—H15C	109.5
C5—C6—H6	121.9	H15A—C15—H15C	109.5
O1—C7—C6	125.14 (14)	H15B—C15—H15C	109.5
O1—C7—C2	110.63 (14)	S1—C16—H16A	109.5
C6—C7—C2	124.23 (15)	S1—C16—H16B	109.5
C1—C8—O1	110.51 (14)	H16A—C16—H16B	109.5
C1—C8—C9	133.98 (15)	S1—C16—H16C	109.5
O1—C8—C9	115.51 (13)	H16A—C16—H16C	109.5
C10—C9—C14	118.87 (15)	H16B—C16—H16C	109.5

O2—S1—C1—C8	142.96 (15)	C1—C2—C7—C6	−179.96 (15)
C16—S1—C1—C8	−107.64 (15)	C2—C1—C8—O1	−0.17 (17)
O2—S1—C1—C2	−29.09 (16)	S1—C1—C8—O1	−173.43 (11)
C16—S1—C1—C2	80.31 (15)	C2—C1—C8—C9	−179.34 (16)
C8—C1—C2—C7	−0.40 (17)	S1—C1—C8—C9	7.4 (3)
S1—C1—C2—C7	172.92 (12)	C7—O1—C8—C1	0.68 (17)
C8—C1—C2—C3	179.75 (17)	C7—O1—C8—C9	−179.99 (12)
S1—C1—C2—C3	−6.9 (3)	C1—C8—C9—C10	29.6 (3)
C7—C2—C3—C4	−0.1 (2)	O1—C8—C9—C10	−149.54 (15)
C1—C2—C3—C4	179.69 (16)	C1—C8—C9—C14	−151.36 (18)
C2—C3—C4—C5	0.1 (2)	O1—C8—C9—C14	29.5 (2)
C2—C3—C4—Cl1	−179.18 (11)	C14—C9—C10—C11	1.5 (2)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—C11	−179.49 (15)
Cl1—C4—C5—C6	179.45 (12)	C9—C10—C11—C12	−1.0 (3)
C4—C5—C6—C7	−0.4 (2)	C10—C11—C12—C13	0.2 (2)
C8—O1—C7—C6	179.86 (15)	C10—C11—C12—C15	179.82 (16)
C8—O1—C7—C2	−0.94 (16)	C11—C12—C13—C14	0.3 (2)
C5—C6—C7—O1	179.43 (14)	C15—C12—C13—C14	−179.38 (16)
C5—C6—C7—C2	0.3 (2)	C12—C13—C14—C9	0.2 (2)
C3—C2—C7—O1	−179.29 (13)	C10—C9—C14—C13	−1.0 (2)
C1—C2—C7—O1	0.83 (17)	C8—C9—C14—C13	179.91 (14)
C3—C2—C7—C6	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.95	2.54	3.436 (2)	158

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClO₂S
M_r	304.77
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.0694 (8), 8.0763 (8), 11.4208 (11)
α, β, γ (°)	90.185 (6), 96.280 (6), 111.701 (6)
V (Å³)	686.63 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.35 × 0.34 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.865, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	12808, 3423, 3021
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.05
No. of reflections	3423
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.28

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···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.95	2.54	3.436 (2)	157.5

Symmetry code: (i) −x+1, −y, −z+1.

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.

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