Crystal structure of 5-chloro-2,4,6-trimethyl-3-(4-methyl­phenyl­sulfin­yl)-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S160053681402385X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1233-o1234

doi:10.1107/S160053681402385X

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Crystal structure of 5-chloro-2,4,6-trimethyl-3-(4-methylphenylsulfinyl)-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 G. S. Nichol, University of Edinburgh, Scotland (Received 19 August 2014; accepted 29 October 2014; online 5 November 2014)

In the title compound, C₁₈H₁₇ClO₂S, the dihedral angle between the planes of the benzofuran ring [r.m.s. deviation = 0.013 (1) Å] and the 4-methylphenyl ring is 87.37 (5)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.525 (2) Å]. In addition, an S⋯S [3.6584 (9) Å] contact is observed.

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

CCDC reference: 1031568

1. Related literature

For the pharmacological properties of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Howlett et al. (1999 ); Wahab 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-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran, see: Choi et al. (1999 ). For a related structure, see: Choi et al. (2012 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₇ClO₂S
M_r = 332.83
Triclinic, $[P \overline 1]$
a = 8.7938 (2) Å
b = 9.1775 (3) Å
c = 10.7298 (3) Å
α = 86.571 (1)°
β = 69.157 (1)°
γ = 81.093 (2)°
V = 799.51 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 173 K
0.60 × 0.56 × 0.08 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.807, T_max = 0.971
14763 measured reflections
3988 independent reflections
3502 reflections with I > 2σ(I)
R_int = 0.048

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.05
3988 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.30	3.180 (2)	154
C17—H17⋯O1ⁱⁱ	0.95	2.56	3.434 (2)	153
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -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

CCDC reference: 1031568

Crystal structure: contains datablock I. DOI: 10.1107/S160053681402385X/nk2227sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681402385X/nk2227Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681402385X/nk2227Isup3.cml

checkCIF report

Comment top

Substituted benzofurans show interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009, Galal et al., 2009, Wahab Khan et al., 2005), and potential inhibitor of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These benzofuran compounds occur in a great number of natural products. (Akgul & Anil, 2003, Soekamto et al., 2003). As a part of our ongoing project of 3-arylsulfinyl-5-chloro-2-methyl-1-benzofuran derivatives containing 4-bromophenylsulfinyl substituent in 3-position (Choi et al., 2012), 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 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.003 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 4-methylphenyl ring is 87.37 (5)°. In the crystal structure (Fig. 2), molecules are linked by C—H···O hydrogen bonds (Table 1) and π–π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱⁱ distance of 3.525 (2) Å and an interplanar distance of 3.479 (2) Å resulting in a slippage of 0.568 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively). In the crystal (Fig. 2), an S1···S1^iv [3.6584 (9) Å] contact are observed.

Related literature top

For the pharmacological properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Wahab 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-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2012).

Experimental top

The starting material 5-chloro-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-chloro-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (285 mg, 0.9 mmol) in dichloromethane (25 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X 10 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 68% (226 mg); m.p. 466–467 K; R_f = 0.43 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (23 mg) in acetone (15 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 the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Fig. 2. A view of the C—H···O, π–π and S···S 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, z; (ii) - x + 1, - y + 2, - z + 1; (iii) - x + 1, - y + 1, - z + 1; (iv) - x, - y + 2, - z + 1; (v) x - 1, y, z; (vi) x, y - 1, z.]

5-Chloro-2,4,6-trimethyl-3-(4-methylphenylsulfinyl)-1-benzofuran top

Crystal data top

C₁₈H₁₇ClO₂S	Z = 2
M_r = 332.83	F(000) = 348
Triclinic, P1	D_x = 1.383 Mg m⁻³
Hall symbol: -P 1	Melting point = 467–466 K
a = 8.7938 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1775 (3) Å	Cell parameters from 6565 reflections
c = 10.7298 (3) Å	θ = 2.6–28.3°
α = 86.571 (1)°	µ = 0.37 mm⁻¹
β = 69.157 (1)°	T = 173 K
γ = 81.093 (2)°	Block, colourless
V = 799.51 (4) Å³	0.60 × 0.56 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3988 independent reflections
Radiation source: rotating anode	3502 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 = 2.0°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.807, T_max = 0.971	l = −11→14
14763 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0641P)² + 0.2785P] where P = (F_o² + 2F_c²)/3
3988 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₈H₁₇ClO₂S	γ = 81.093 (2)°
M_r = 332.83	V = 799.51 (4) Å³
Triclinic, P1	Z = 2
a = 8.7938 (2) Å	Mo Kα radiation
b = 9.1775 (3) Å	µ = 0.37 mm⁻¹
c = 10.7298 (3) Å	T = 173 K
α = 86.571 (1)°	0.60 × 0.56 × 0.08 mm
β = 69.157 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3988 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3502 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.971	R_int = 0.048
14763 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	Δρ_max = 0.83 e Å⁻³
3988 reflections	Δρ_min = −0.41 e Å⁻³
203 parameters

Special details top

Experimental. ¹H NMR (δ p.p.m., CDCl₃, 400 Hz): 7.34 (d, J = 8.24 Hz, 2H), 7.22 (d, J = 7.84 Hz, 2H), 7.19 (s, 1H), 2.71 (s, 3H), 2.43 (s, 3H), 2.37 (s, 3H), 2.32 (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	0.73398 (7)	0.38071 (5)	0.09920 (5)	0.04987 (16)
S1	0.14021 (5)	0.82594 (5)	0.46437 (4)	0.03532 (13)
O1	0.54038 (13)	0.77389 (12)	0.54951 (11)	0.0305 (2)
O2	0.06142 (17)	0.69774 (17)	0.45239 (15)	0.0502 (4)
C1	0.33771 (18)	0.76626 (16)	0.46945 (16)	0.0281 (3)
C2	0.47994 (18)	0.66515 (15)	0.39027 (15)	0.0256 (3)
C3	0.5174 (2)	0.56896 (16)	0.28374 (16)	0.0298 (3)
C4	0.6780 (2)	0.49579 (17)	0.23736 (16)	0.0321 (3)
C5	0.7994 (2)	0.50928 (18)	0.29109 (17)	0.0330 (3)
C6	0.75771 (19)	0.60170 (17)	0.39906 (16)	0.0315 (3)
H6	0.8345	0.6131	0.4403	0.038*
C7	0.60010 (19)	0.67636 (16)	0.44414 (15)	0.0265 (3)
C8	0.38130 (19)	0.82609 (17)	0.56227 (16)	0.0296 (3)
C9	0.3921 (3)	0.5445 (2)	0.2249 (2)	0.0471 (5)
H9A	0.4114	0.5990	0.1406	0.071*
H9B	0.2817	0.5794	0.2872	0.071*
H9C	0.4015	0.4390	0.2084	0.071*
C10	0.9703 (2)	0.4263 (2)	0.2351 (2)	0.0486 (5)
H10A	1.0322	0.4416	0.2921	0.073*
H10B	1.0256	0.4623	0.1449	0.073*
H10C	0.9645	0.3209	0.2320	0.073*
C11	0.2955 (2)	0.9357 (2)	0.66964 (18)	0.0405 (4)
H11A	0.3379	1.0297	0.6427	0.061*
H11B	0.3145	0.9000	0.7515	0.061*
H11C	0.1773	0.9499	0.6857	0.061*
C12	0.19683 (19)	0.91671 (17)	0.30487 (16)	0.0303 (3)
C13	0.1421 (2)	0.87745 (19)	0.20800 (19)	0.0374 (4)
H13	0.0840	0.7954	0.2211	0.045*
C14	0.1729 (2)	0.9595 (2)	0.09110 (19)	0.0426 (4)
H14	0.1359	0.9324	0.0238	0.051*
C15	0.2563 (3)	1.07992 (19)	0.07025 (18)	0.0433 (4)
C16	0.3090 (3)	1.11627 (19)	0.1702 (2)	0.0448 (4)
H16	0.3671	1.1982	0.1576	0.054*
C17	0.2795 (2)	1.03701 (19)	0.28696 (19)	0.0383 (4)
H17	0.3155	1.0645	0.3547	0.046*
C18	0.2873 (4)	1.1712 (2)	−0.0548 (2)	0.0668 (7)
H18A	0.4004	1.1425	−0.1153	0.100*
H18B	0.2711	1.2758	−0.0323	0.100*
H18C	0.2105	1.1550	−0.0983	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0693 (3)	0.0399 (2)	0.0368 (2)	0.0026 (2)	−0.0170 (2)	−0.01002 (18)
S1	0.0252 (2)	0.0470 (3)	0.0337 (2)	−0.00534 (16)	−0.01096 (16)	0.00375 (17)
O1	0.0335 (6)	0.0326 (5)	0.0308 (6)	−0.0075 (4)	−0.0165 (5)	−0.0015 (4)
O2	0.0404 (7)	0.0647 (9)	0.0563 (9)	−0.0267 (6)	−0.0252 (7)	0.0181 (7)
C1	0.0271 (7)	0.0302 (7)	0.0285 (7)	−0.0066 (6)	−0.0109 (6)	0.0033 (6)
C2	0.0271 (7)	0.0255 (6)	0.0278 (7)	−0.0082 (5)	−0.0129 (6)	0.0045 (5)
C3	0.0373 (8)	0.0276 (7)	0.0295 (8)	−0.0077 (6)	−0.0168 (7)	0.0012 (6)
C4	0.0420 (9)	0.0266 (7)	0.0274 (7)	−0.0058 (6)	−0.0116 (7)	0.0016 (6)
C5	0.0314 (8)	0.0323 (8)	0.0312 (8)	−0.0045 (6)	−0.0072 (6)	0.0067 (6)
C6	0.0292 (7)	0.0346 (8)	0.0342 (8)	−0.0089 (6)	−0.0146 (6)	0.0059 (6)
C7	0.0298 (7)	0.0264 (7)	0.0265 (7)	−0.0085 (5)	−0.0123 (6)	0.0024 (5)
C8	0.0309 (7)	0.0297 (7)	0.0293 (8)	−0.0062 (6)	−0.0117 (6)	0.0031 (6)
C9	0.0541 (11)	0.0450 (10)	0.0563 (12)	−0.0038 (8)	−0.0359 (10)	−0.0133 (9)
C10	0.0346 (9)	0.0530 (11)	0.0465 (11)	0.0025 (8)	−0.0043 (8)	0.0032 (9)
C11	0.0484 (10)	0.0385 (9)	0.0327 (9)	−0.0041 (7)	−0.0122 (8)	−0.0044 (7)
C12	0.0262 (7)	0.0323 (7)	0.0310 (8)	0.0008 (6)	−0.0103 (6)	0.0003 (6)
C13	0.0385 (9)	0.0350 (8)	0.0419 (9)	−0.0027 (7)	−0.0190 (8)	−0.0017 (7)
C14	0.0548 (11)	0.0390 (9)	0.0354 (9)	0.0051 (8)	−0.0216 (8)	−0.0067 (7)
C15	0.0565 (11)	0.0307 (8)	0.0335 (9)	0.0074 (7)	−0.0097 (8)	−0.0024 (7)
C16	0.0544 (11)	0.0300 (8)	0.0477 (11)	−0.0071 (8)	−0.0149 (9)	0.0007 (7)
C17	0.0429 (9)	0.0356 (8)	0.0399 (9)	−0.0045 (7)	−0.0190 (8)	−0.0032 (7)
C18	0.105 (2)	0.0425 (11)	0.0395 (11)	0.0014 (12)	−0.0150 (12)	0.0042 (9)

Geometric parameters (Å, º) top

Cl1—C4	1.7500 (16)	C9—H9C	0.9800
S1—O2	1.4882 (14)	C10—H10A	0.9800
S1—C1	1.7574 (15)	C10—H10B	0.9800
S1—C12	1.7950 (17)	C10—H10C	0.9800
S1—S1ⁱ	3.6584 (9)	C11—H11A	0.9800
O1—C8	1.3672 (19)	C11—H11B	0.9800
O1—C7	1.3813 (18)	C11—H11C	0.9800
C1—C8	1.357 (2)	C12—C13	1.377 (2)
C1—C2	1.458 (2)	C12—C17	1.381 (2)
C2—C7	1.392 (2)	C13—C14	1.386 (3)
C2—C3	1.399 (2)	C13—H13	0.9500
C3—C4	1.393 (2)	C14—C15	1.384 (3)
C3—C9	1.501 (2)	C14—H14	0.9500
C4—C5	1.405 (2)	C15—C16	1.386 (3)
C5—C6	1.384 (2)	C15—C18	1.501 (3)
C5—C10	1.502 (2)	C16—C17	1.372 (3)
C6—C7	1.376 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.481 (2)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800

O2—S1—C1	110.50 (8)	C5—C10—H10A	109.5
O2—S1—C12	106.80 (8)	C5—C10—H10B	109.5
C1—S1—C12	98.98 (7)	H10A—C10—H10B	109.5
O2—S1—S1ⁱ	113.79 (6)	C5—C10—H10C	109.5
C1—S1—S1ⁱ	134.58 (5)	H10A—C10—H10C	109.5
C12—S1—S1ⁱ	77.68 (5)	H10B—C10—H10C	109.5
C8—O1—C7	106.51 (11)	C8—C11—H11A	109.5
C8—C1—C2	107.06 (13)	C8—C11—H11B	109.5
C8—C1—S1	118.18 (12)	H11A—C11—H11B	109.5
C2—C1—S1	134.71 (12)	C8—C11—H11C	109.5
C7—C2—C3	118.93 (14)	H11A—C11—H11C	109.5
C7—C2—C1	104.37 (13)	H11B—C11—H11C	109.5
C3—C2—C1	136.70 (14)	C13—C12—C17	120.71 (16)
C4—C3—C2	115.52 (14)	C13—C12—S1	120.19 (13)
C4—C3—C9	122.27 (15)	C17—C12—S1	118.68 (13)
C2—C3—C9	122.20 (15)	C12—C13—C14	119.00 (17)
C3—C4—C5	125.18 (15)	C12—C13—H13	120.5
C3—C4—Cl1	117.32 (12)	C14—C13—H13	120.5
C5—C4—Cl1	117.49 (13)	C15—C14—C13	121.47 (17)
C6—C5—C4	118.13 (15)	C15—C14—H14	119.3
C6—C5—C10	119.95 (16)	C13—C14—H14	119.3
C4—C5—C10	121.92 (17)	C14—C15—C16	117.83 (17)
C7—C6—C5	117.09 (14)	C14—C15—C18	121.9 (2)
C7—C6—H6	121.5	C16—C15—C18	120.3 (2)
C5—C6—H6	121.5	C17—C16—C15	121.75 (18)
C6—C7—O1	124.07 (13)	C17—C16—H16	119.1
C6—C7—C2	125.10 (14)	C15—C16—H16	119.1
O1—C7—C2	110.83 (13)	C16—C17—C12	119.23 (16)
C1—C8—O1	111.21 (13)	C16—C17—H17	120.4
C1—C8—C11	133.88 (15)	C12—C17—H17	120.4
O1—C8—C11	114.89 (14)	C15—C18—H18A	109.5
C3—C9—H9A	109.5	C15—C18—H18B	109.5
C3—C9—H9B	109.5	H18A—C18—H18B	109.5
H9A—C9—H9B	109.5	C15—C18—H18C	109.5
C3—C9—H9C	109.5	H18A—C18—H18C	109.5
H9A—C9—H9C	109.5	H18B—C18—H18C	109.5
H9B—C9—H9C	109.5

O2—S1—C1—C8	−134.63 (14)	C8—O1—C7—C2	−0.45 (16)
C12—S1—C1—C8	113.57 (14)	C3—C2—C7—C6	1.5 (2)
S1ⁱ—S1—C1—C8	32.06 (17)	C1—C2—C7—C6	−178.85 (15)
O2—S1—C1—C2	48.36 (18)	C3—C2—C7—O1	−178.86 (13)
C12—S1—C1—C2	−63.44 (17)	C1—C2—C7—O1	0.82 (16)
S1ⁱ—S1—C1—C2	−144.96 (13)	C2—C1—C8—O1	0.66 (18)
C8—C1—C2—C7	−0.88 (17)	S1—C1—C8—O1	−177.12 (10)
S1—C1—C2—C7	176.36 (13)	C2—C1—C8—C11	179.10 (17)
C8—C1—C2—C3	178.70 (17)	S1—C1—C8—C11	1.3 (3)
S1—C1—C2—C3	−4.1 (3)	C7—O1—C8—C1	−0.16 (17)
C7—C2—C3—C4	−2.4 (2)	C7—O1—C8—C11	−178.91 (13)
C1—C2—C3—C4	178.08 (16)	O2—S1—C12—C13	10.13 (16)
C7—C2—C3—C9	176.67 (16)	C1—S1—C12—C13	124.85 (14)
C1—C2—C3—C9	−2.9 (3)	S1ⁱ—S1—C12—C13	−101.30 (13)
C2—C3—C4—C5	1.6 (2)	O2—S1—C12—C17	−177.26 (13)
C9—C3—C4—C5	−177.46 (17)	C1—S1—C12—C17	−62.55 (14)
C2—C3—C4—Cl1	−177.10 (11)	S1ⁱ—S1—C12—C17	71.31 (13)
C9—C3—C4—Cl1	3.8 (2)	C17—C12—C13—C14	0.8 (2)
C3—C4—C5—C6	0.3 (3)	S1—C12—C13—C14	173.25 (13)
Cl1—C4—C5—C6	179.01 (12)	C12—C13—C14—C15	−0.4 (3)
C3—C4—C5—C10	179.99 (16)	C13—C14—C15—C16	0.2 (3)
Cl1—C4—C5—C10	−1.3 (2)	C13—C14—C15—C18	−178.73 (18)
C4—C5—C6—C7	−1.3 (2)	C14—C15—C16—C17	−0.4 (3)
C10—C5—C6—C7	178.96 (15)	C18—C15—C16—C17	178.56 (19)
C5—C6—C7—O1	−179.13 (14)	C15—C16—C17—C12	0.8 (3)
C5—C6—C7—C2	0.5 (2)	C13—C12—C17—C16	−1.0 (3)
C8—O1—C7—C6	179.22 (15)	S1—C12—C17—C16	−173.55 (13)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱⁱ	0.95	2.30	3.180 (2)	154
C17—H17···O1ⁱⁱⁱ	0.95	2.56	3.434 (2)	153

Symmetry codes: (ii) x+1, y, z; (iii) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.30	3.180 (2)	154.3
C17—H17···O1ⁱⁱ	0.95	2.56	3.434 (2)	153.1

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+1.

Acknowledgements

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

References

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Volume 70| Part 12| December 2014| Pages o1233-o1234

doi:10.1107/S160053681402385X

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

Crystal structure of 5-chloro-2,4,6-tri­methyl-3-(4-methyl­phenyl­sulfin­yl)-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-2,4,6-trimethyl-3-(4-methylphenylsulfinyl)-1-benzofuran