Crystal structure of 5-chloro-2,7-dimethyl-3-[(4-methyl­phenyl)­sulfon­yl]-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S1600536814018339

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1018-o1019

doi:10.1107/S1600536814018339

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Crystal structure of 5-chloro-2,7-dimethyl-3-[(4-methylphenyl)sulfonyl]-1-benzofuran

Hong Dae Choi ^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 August 2014; accepted 12 August 2014; online 16 August 2014)

In the title compound, C₁₇H₁₅ClO₃S, the dihedral angle between the planes of the benzofuran ring system [r.m.s. deviation = 0.008 Å] and the 4-methylphenyl ring is 77.29 (4)°. In the crystal, molecules are linked by π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.847 (2) Å] and between the benzene and furan rings of neighbouring molecules [centroid–centroid distance = 3.743 (2) Å]. The molecules are stacked along the a-axis direction. In addition, pairs of C—H⋯O hydrogen bonds are observed between inversion-related dimers: these generate R₂²(12) loops.

Keywords: crystal structure; benzofuran; 4-methylphenyl; C—H⋯O hydrogen bonds; π–π interactions.

CCDC reference: 1018954

1. Related literature

For the pharmaceutical properties of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Howlett et al. (1999 ); Khan et al. (2005 ); Ono et al. (2002 ). For natural products with a benzofuran ring, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the synthesis of the starting material 5-chloro-2,7-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran, see: Choi et al. (1999 ). For a related structure, see: Choi et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₅ClO₃S
M_r = 334.80
Triclinic, $[P \overline 1]$
a = 8.2757 (2) Å
b = 9.6740 (2) Å
c = 10.1564 (2) Å
α = 76.655 (1)°
β = 75.673 (1)°
γ = 76.355 (1)°
V = 752.64 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 173 K
0.35 × 0.32 × 0.25 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.871, T_max = 0.905
14105 measured reflections
3745 independent reflections
3274 reflections with I > 2σ(I)
R_int = 0.023

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.099
S = 1.05
3745 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.52	3.269 (2)	136
Symmetry code: (i) -x+1, -y+1, -z.

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

CCDC reference: 1018954

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814018339/hb7272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018339/hb7272Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018339/hb7272Isup3.cml

checkCIF report

Comment top

Benzofuran compounds show various pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009, Galal et al., 2009, Khan et al., 2005), and potential inhibitor of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These benzofuran compounds are widely occurring in nature (Akgul & Anil, 2003, Soekamto et al., 2003). As a part of our ongoing project of 3-arylsulfonyl-5-chloro-2,7-dimethyl-1-benzofuran derivatives containing 3-methylphenylsulfonyl substituent in 3-position (Choi et al., 2014), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is essentially planar, with a mean deviation of 0.006 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-methylphenyl ring is 77.29 (4)°. In the crystal structure (Fig. 2), molecules are linked by π···π interactions between the benzene rings of neighbouring molecules with a Cg1···Cg1ⁱⁱ distance of 3.847 (2) Å and an interplanar distance of 3.479 (2) Å resulting in a slippage of 1.642 (2) Å (Cg1 is the centroid of the C2–C7 benzene ring), and between the benzene and furan rings of neighbouring molecules with a Cg1···Cg2ⁱⁱⁱ distance of 3.743 (2) Å and an interplanar distance of 3.595 (2) Å resulting in a slippage of 1.042 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring). The molecules are stacked along the a-axis direction. In addition, intermolecular C—H···O hydrogen bonds (Table 1) are observed between inversion-related dimers.

Related literature top

For the pharmaceutical properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Khan et al. (2005); Ono et al. (2002). For natural products with a benzofuran ring, see: Akgul & Anil (2003); Soekamto et al. (2003). For the synthesis of the starting material 5-chloro-2,7-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2014).

Experimental top

The starting material 5-chloro-2,7-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-chloro-3-(4-methylphenylsulfanyl)-2,7-dimethyl-1-benzofuran (333 mg, 1.1 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 × 20 ml) 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 69% (254 mg); m.p. 468–469 K; R_f = 0.61 (hexane–ethyl acetate, 4:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound (25 mg) in ethyl acetate (20 ml) 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 with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the C—H···O and π···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 + 1, - y + 1, - z; (ii) - x + 1, - y + 1, - z + 1; (iii) - x, - y + 1, - z + 1; (iv) x + 1, y, z; (v) x + 1 , y, z.]

5-Chloro-2,7-dimethyl-3-[(4-methylphenyl)sulfonyl]-1-benzofuran top

Crystal data top

C₁₇H₁₅ClO₃S	Z = 2
M_r = 334.80	F(000) = 348
Triclinic, P1	D_x = 1.477 Mg m⁻³
Hall symbol: -P 1	Melting point = 469–468 K
a = 8.2757 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6740 (2) Å	Cell parameters from 5796 reflections
c = 10.1564 (2) Å	θ = 2.6–28.4°
α = 76.655 (1)°	µ = 0.40 mm⁻¹
β = 75.673 (1)°	T = 173 K
γ = 76.355 (1)°	Block, colourless
V = 752.64 (3) Å³	0.35 × 0.32 × 0.25 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3745 independent reflections
Radiation source: rotating anode	3274 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.1°
ϕ and ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.871, T_max = 0.905	l = −13→13
14105 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.050P)² + 0.3424P] where P = (F_o² + 2F_c²)/3
3745 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₇H₁₅ClO₃S	γ = 76.355 (1)°
M_r = 334.80	V = 752.64 (3) Å³
Triclinic, P1	Z = 2
a = 8.2757 (2) Å	Mo Kα radiation
b = 9.6740 (2) Å	µ = 0.40 mm⁻¹
c = 10.1564 (2) Å	T = 173 K
α = 76.655 (1)°	0.35 × 0.32 × 0.25 mm
β = 75.673 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3745 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3274 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.905	R_int = 0.023
14105 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
3745 reflections	Δρ_min = −0.32 e Å⁻³
202 parameters

Special details top

Experimental. ¹H NMR (δ p.p.m., CDCl3, 400 Hz): 7.87 (d, J = 8.56 Hz, 2H), 7.68 (s, 1H),7.31 (d, J = 8.24 Hz, 2H), 7.07-7.09 (m, 1H), 2.80 (s, 3H), 2.42 (s, 3H), 2.39 (s, 3H).

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	0.49131 (6)	0.18481 (4)	0.50226 (5)	0.03579 (12)
S1	0.09180 (5)	0.67869 (4)	0.15275 (4)	0.02306 (11)
O1	0.06794 (14)	0.75353 (12)	0.52188 (11)	0.0243 (2)
O2	0.11863 (15)	0.52962 (13)	0.14105 (12)	0.0301 (3)
O3	−0.05754 (14)	0.77699 (13)	0.11729 (12)	0.0312 (3)
C1	0.09965 (19)	0.67929 (16)	0.32240 (14)	0.0219 (3)
C2	0.19361 (19)	0.56512 (16)	0.40987 (14)	0.0216 (3)
C3	0.29224 (19)	0.42829 (16)	0.39832 (15)	0.0240 (3)
H3	0.3099	0.3878	0.3179	0.029*
C4	0.3628 (2)	0.35505 (17)	0.51112 (16)	0.0259 (3)
C5	0.3387 (2)	0.41057 (18)	0.63123 (16)	0.0276 (3)
H5	0.3907	0.3547	0.7051	0.033*
C6	0.2401 (2)	0.54586 (18)	0.64457 (15)	0.0252 (3)
C7	0.16990 (19)	0.61807 (16)	0.53085 (15)	0.0224 (3)
C8	0.02745 (19)	0.78847 (17)	0.39395 (15)	0.0238 (3)
C9	0.2140 (2)	0.6124 (2)	0.76979 (16)	0.0324 (4)
H9A	0.3006	0.6710	0.7560	0.049*
H9B	0.2235	0.5356	0.8511	0.049*
H9C	0.1010	0.6738	0.7841	0.049*
C10	−0.0811 (2)	0.93214 (18)	0.36327 (17)	0.0302 (3)
H10A	−0.1029	0.9475	0.2699	0.045*
H10B	−0.0233	1.0074	0.3691	0.045*
H10C	−0.1891	0.9368	0.4305	0.045*
C11	0.27059 (19)	0.74903 (17)	0.05186 (14)	0.0230 (3)
C12	0.4317 (2)	0.66660 (18)	0.05643 (17)	0.0299 (3)
H12	0.4454	0.5743	0.1148	0.036*
C13	0.5723 (2)	0.72047 (19)	−0.02508 (18)	0.0325 (4)
H13	0.6829	0.6650	−0.0214	0.039*
C14	0.5538 (2)	0.85464 (19)	−0.11220 (16)	0.0294 (3)
C15	0.3924 (2)	0.93542 (19)	−0.11401 (17)	0.0339 (4)
H15	0.3785	1.0278	−0.1723	0.041*
C16	0.2502 (2)	0.88400 (18)	−0.03225 (17)	0.0300 (3)
H16	0.1399	0.9409	−0.0339	0.036*
C17	0.7084 (2)	0.9091 (2)	−0.2026 (2)	0.0413 (4)
H17A	0.7429	0.8668	−0.2865	0.062*
H17B	0.8014	0.8811	−0.1522	0.062*
H17C	0.6815	1.0148	−0.2279	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0358 (2)	0.0238 (2)	0.0425 (2)	−0.00058 (16)	−0.00815 (18)	−0.00056 (16)
S1	0.02253 (19)	0.0282 (2)	0.01904 (17)	−0.00402 (14)	−0.00553 (13)	−0.00488 (13)
O1	0.0263 (5)	0.0257 (5)	0.0213 (5)	−0.0033 (4)	−0.0049 (4)	−0.0068 (4)
O2	0.0349 (6)	0.0318 (6)	0.0270 (6)	−0.0095 (5)	−0.0057 (5)	−0.0093 (5)
O3	0.0249 (6)	0.0400 (7)	0.0274 (6)	−0.0017 (5)	−0.0096 (5)	−0.0038 (5)
C1	0.0221 (7)	0.0248 (7)	0.0190 (6)	−0.0043 (6)	−0.0042 (5)	−0.0043 (5)
C2	0.0217 (7)	0.0238 (7)	0.0194 (6)	−0.0066 (6)	−0.0034 (5)	−0.0027 (5)
C3	0.0247 (7)	0.0241 (7)	0.0231 (7)	−0.0058 (6)	−0.0035 (6)	−0.0043 (6)
C4	0.0241 (7)	0.0220 (7)	0.0291 (7)	−0.0047 (6)	−0.0046 (6)	−0.0001 (6)
C5	0.0288 (8)	0.0304 (8)	0.0241 (7)	−0.0099 (6)	−0.0087 (6)	0.0019 (6)
C6	0.0261 (8)	0.0307 (8)	0.0204 (7)	−0.0106 (6)	−0.0047 (6)	−0.0026 (6)
C7	0.0220 (7)	0.0238 (7)	0.0213 (7)	−0.0056 (6)	−0.0028 (5)	−0.0045 (5)
C8	0.0227 (7)	0.0268 (8)	0.0218 (7)	−0.0054 (6)	−0.0038 (5)	−0.0043 (6)
C9	0.0376 (9)	0.0400 (10)	0.0227 (7)	−0.0106 (7)	−0.0086 (6)	−0.0061 (7)
C10	0.0296 (8)	0.0278 (8)	0.0318 (8)	0.0006 (6)	−0.0078 (6)	−0.0073 (6)
C11	0.0243 (7)	0.0269 (8)	0.0176 (6)	−0.0042 (6)	−0.0035 (5)	−0.0054 (5)
C12	0.0282 (8)	0.0270 (8)	0.0309 (8)	−0.0019 (6)	−0.0062 (6)	−0.0011 (6)
C13	0.0230 (8)	0.0355 (9)	0.0353 (9)	−0.0001 (7)	−0.0034 (6)	−0.0074 (7)
C14	0.0305 (8)	0.0351 (9)	0.0231 (7)	−0.0090 (7)	−0.0013 (6)	−0.0082 (6)
C15	0.0366 (9)	0.0313 (9)	0.0286 (8)	−0.0061 (7)	−0.0058 (7)	0.0033 (7)
C16	0.0271 (8)	0.0309 (8)	0.0277 (8)	−0.0008 (6)	−0.0067 (6)	−0.0005 (6)
C17	0.0350 (10)	0.0507 (12)	0.0362 (9)	−0.0159 (9)	0.0027 (7)	−0.0069 (8)

Geometric parameters (Å, º) top

Cl1—C4	1.7452 (16)	C9—H9B	0.9800
S1—O2	1.4346 (12)	C9—H9C	0.9800
S1—O3	1.4384 (11)	C10—H10A	0.9800
S1—C1	1.7417 (14)	C10—H10B	0.9800
S1—C11	1.7621 (16)	C10—H10C	0.9800
O1—C8	1.3690 (17)	C11—C16	1.384 (2)
O1—C7	1.3779 (18)	C11—C12	1.388 (2)
C1—C8	1.357 (2)	C12—C13	1.386 (2)
C1—C2	1.448 (2)	C12—H12	0.9500
C2—C7	1.391 (2)	C13—C14	1.391 (2)
C2—C3	1.395 (2)	C13—H13	0.9500
C3—C4	1.385 (2)	C14—C15	1.382 (2)
C3—H3	0.9500	C14—C17	1.507 (2)
C4—C5	1.396 (2)	C15—C16	1.387 (2)
C5—C6	1.386 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.388 (2)	C17—H17A	0.9800
C6—C9	1.501 (2)	C17—H17B	0.9800
C8—C10	1.478 (2)	C17—H17C	0.9800
C9—H9A	0.9800

O2—S1—O3	119.70 (7)	C6—C9—H9C	109.5
O2—S1—C1	106.30 (7)	H9A—C9—H9C	109.5
O3—S1—C1	109.53 (7)	H9B—C9—H9C	109.5
O2—S1—C11	107.88 (7)	C8—C10—H10A	109.5
O3—S1—C11	107.90 (7)	C8—C10—H10B	109.5
C1—S1—C11	104.52 (7)	H10A—C10—H10B	109.5
C8—O1—C7	107.01 (11)	C8—C10—H10C	109.5
C8—C1—C2	107.66 (13)	H10A—C10—H10C	109.5
C8—C1—S1	126.70 (12)	H10B—C10—H10C	109.5
C2—C1—S1	125.56 (12)	C16—C11—C12	120.52 (15)
C7—C2—C3	119.58 (13)	C16—C11—S1	120.29 (12)
C7—C2—C1	104.47 (13)	C12—C11—S1	119.18 (12)
C3—C2—C1	135.95 (14)	C13—C12—C11	119.26 (15)
C4—C3—C2	115.94 (14)	C13—C12—H12	120.4
C4—C3—H3	122.0	C11—C12—H12	120.4
C2—C3—H3	122.0	C12—C13—C14	120.91 (15)
C3—C4—C5	123.62 (15)	C12—C13—H13	119.5
C3—C4—Cl1	118.36 (13)	C14—C13—H13	119.5
C5—C4—Cl1	118.01 (12)	C15—C14—C13	118.81 (15)
C6—C5—C4	121.09 (14)	C15—C14—C17	121.28 (16)
C6—C5—H5	119.5	C13—C14—C17	119.92 (16)
C4—C5—H5	119.5	C14—C15—C16	121.12 (15)
C5—C6—C7	114.72 (14)	C14—C15—H15	119.4
C5—C6—C9	123.22 (14)	C16—C15—H15	119.4
C7—C6—C9	122.03 (15)	C11—C16—C15	119.36 (15)
O1—C7—C6	124.46 (14)	C11—C16—H16	120.3
O1—C7—C2	110.50 (13)	C15—C16—H16	120.3
C6—C7—C2	125.05 (15)	C14—C17—H17A	109.5
C1—C8—O1	110.35 (13)	C14—C17—H17B	109.5
C1—C8—C10	134.26 (14)	H17A—C17—H17B	109.5
O1—C8—C10	115.39 (13)	C14—C17—H17C	109.5
C6—C9—H9A	109.5	H17A—C17—H17C	109.5
C6—C9—H9B	109.5	H17B—C17—H17C	109.5
H9A—C9—H9B	109.5

O2—S1—C1—C8	−156.13 (14)	C1—C2—C7—O1	0.67 (16)
O3—S1—C1—C8	−25.47 (16)	C3—C2—C7—C6	1.2 (2)
C11—S1—C1—C8	89.91 (15)	C1—C2—C7—C6	−178.72 (14)
O2—S1—C1—C2	27.64 (15)	C2—C1—C8—O1	0.08 (17)
O3—S1—C1—C2	158.29 (13)	S1—C1—C8—O1	−176.71 (11)
C11—S1—C1—C2	−86.32 (14)	C2—C1—C8—C10	179.75 (17)
C8—C1—C2—C7	−0.45 (17)	S1—C1—C8—C10	3.0 (3)
S1—C1—C2—C7	176.38 (11)	C7—O1—C8—C1	0.34 (17)
C8—C1—C2—C3	179.68 (17)	C7—O1—C8—C10	−179.40 (13)
S1—C1—C2—C3	−3.5 (3)	O2—S1—C11—C16	136.28 (13)
C7—C2—C3—C4	−1.0 (2)	O3—S1—C11—C16	5.64 (15)
C1—C2—C3—C4	178.86 (16)	C1—S1—C11—C16	−110.88 (14)
C2—C3—C4—C5	0.5 (2)	O2—S1—C11—C12	−42.86 (14)
C2—C3—C4—Cl1	−178.70 (11)	O3—S1—C11—C12	−173.49 (13)
C3—C4—C5—C6	0.0 (2)	C1—S1—C11—C12	69.99 (14)
Cl1—C4—C5—C6	179.14 (12)	C16—C11—C12—C13	−0.5 (2)
C4—C5—C6—C7	0.1 (2)	S1—C11—C12—C13	178.65 (13)
C4—C5—C6—C9	−178.22 (15)	C11—C12—C13—C14	−0.8 (3)
C8—O1—C7—C6	178.75 (14)	C12—C13—C14—C15	1.5 (3)
C8—O1—C7—C2	−0.64 (16)	C12—C13—C14—C17	−178.38 (17)
C5—C6—C7—O1	180.00 (14)	C13—C14—C15—C16	−0.8 (3)
C9—C6—C7—O1	−1.6 (2)	C17—C14—C15—C16	179.00 (17)
C5—C6—C7—C2	−0.7 (2)	C12—C11—C16—C15	1.1 (3)
C9—C6—C7—C2	177.66 (15)	S1—C11—C16—C15	−178.02 (13)
C3—C2—C7—O1	−179.44 (13)	C14—C15—C16—C11	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.52	3.269 (2)	136

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.52	3.269 (2)	136

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The X-ray centre of Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol.Res. 164, 191–195. CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J. & Lee, U. (2014). Acta Cryst. E70, o568. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J. & Son, B. W. (1999). J. Korean Chem. Soc. 43, 606–608. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Ono, M., Kung, M. P., Hou, C. & Kung, H. F. (2002). Nucl. Med. Biol. 29, 633–642. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 70| Part 9| September 2014| Pages o1018-o1019

doi:10.1107/S1600536814018339

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 5-chloro-2,7-di­methyl-3-[(4-methyl­phenyl)­sulfon­yl]-1-benzo­furan

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 5-chloro-2,7-dimethyl-3-[(4-methylphenyl)sulfonyl]-1-benzofuran