3-Cyclo­hexyl­sulfonyl-2,5-dimethyl-1-benzofuran

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

doi:10.1107/S160053681101498X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1225

doi:10.1107/S160053681101498X

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3-Cyclohexylsulfonyl-2,5-dimethyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi ^b 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 April 2011; accepted 21 April 2011; online 29 April 2011)

In the title compound, C₁₆H₂₀O₃S, the cyclohexyl ring adopts a chair conformation and the arylsulfonyl unit is in the equatorial position. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

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 structural studies of related 3-cyclohexylsulfonyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ,b ).

Experimental

Crystal data

C₁₆H₂₀O₃S
M_r = 292.38
Monoclinic, P 2₁ /c
a = 5.6854 (3) Å
b = 21.2391 (13) Å
c = 12.3944 (7) Å
β = 99.295 (3)°
V = 1477.01 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.643, T_max = 0.746
13128 measured reflections
3228 independent reflections
2477 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.05
3228 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	1.00	2.31	3.273 (2)	161
C12—H12B⋯O3ⁱⁱ	0.99	2.57	3.443 (2)	146
C10—H10C⋯Cgⁱⁱⁱ	0.99	2.75	3.556 (2)	140
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, 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 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101498X/gk2370sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101498X/gk2370Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681101498X/gk2370Isup3.cml

checkCIF report

Comment top

Many compounds containing a benzofuran ring have drawn much attention owing to their diverse 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 study of the substituent effect on the solid state structures of 3-cyclohexylsulfonyl-2-methyl-1-benzofuran analogues (Choi et al., 2011a,b), 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 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing (Fig. 2) is stabilized by weak intermolecular C–H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C11–H11···O2ⁱ), and the second one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C12–H12B···O3ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C–H···π interactions between a methyl H atom and the benzene ring (Table 1; C10–H10C···Cgⁱⁱⁱ, 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 structural studies of related 3-cyclohexylsulfonyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (515 mg, 2.3 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-2,5-dimethyl-1-benzofuran (286 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 417-418 K; R_f = 0.66 (hexane-ethyl acetate, 4:1 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.

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

	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.
	Fig. 2. A view of the C–H···O and C–H···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 1, y, z; (ii) x, - y + 1/2, z + 1/2; (iii) x + 1, y, z; (iv) x, - y + 1/2, z - 1/2.]

3-Cyclohexylsulfonyl-2,5-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₂₀O₃S	F(000) = 624
M_r = 292.38	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4533 reflections
a = 5.6854 (3) Å	θ = 2.5–27.0°
b = 21.2391 (13) Å	µ = 0.22 mm⁻¹
c = 12.3944 (7) Å	T = 173 K
β = 99.295 (3)°	Block, colourless
V = 1477.01 (15) Å³	0.30 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3228 independent reflections
Radiation source: rotating anode	2477 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.035
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ϕ and ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→27
T_min = 0.643, T_max = 0.746	l = −15→15
13128 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.106	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0473P)² + 0.5178P] where P = (F_o² + 2F_c²)/3
3228 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₆H₂₀O₃S	V = 1477.01 (15) Å³
M_r = 292.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.6854 (3) Å	µ = 0.22 mm⁻¹
b = 21.2391 (13) Å	T = 173 K
c = 12.3944 (7) Å	0.30 × 0.22 × 0.20 mm
β = 99.295 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3228 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2477 reflections with I > 2σ(I)
T_min = 0.643, T_max = 0.746	R_int = 0.035
13128 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
3228 reflections	Δρ_min = −0.34 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
S1	0.53749 (8)	0.23293 (2)	0.54070 (4)	0.02970 (14)
O1	0.5649 (2)	0.36998 (6)	0.75483 (10)	0.0354 (3)
O2	0.7773 (2)	0.21003 (7)	0.56894 (12)	0.0420 (4)
O3	0.4559 (2)	0.25126 (6)	0.42912 (10)	0.0388 (3)
C1	0.5009 (3)	0.29734 (8)	0.62295 (14)	0.0296 (4)
C2	0.3075 (3)	0.34199 (8)	0.60232 (14)	0.0284 (4)
C3	0.1036 (3)	0.34955 (8)	0.52479 (14)	0.0309 (4)
H3	0.0678	0.3204	0.4663	0.037*
C4	−0.0470 (3)	0.39994 (9)	0.53367 (15)	0.0335 (4)
C5	0.0095 (4)	0.44219 (9)	0.62117 (16)	0.0388 (5)
H5	−0.0956	0.4763	0.6272	0.047*
C6	0.2113 (4)	0.43607 (9)	0.69861 (16)	0.0392 (5)
H6	0.2484	0.4652	0.7571	0.047*
C7	0.3561 (3)	0.38557 (8)	0.68658 (14)	0.0315 (4)
C8	0.6487 (3)	0.31577 (9)	0.71474 (14)	0.0332 (4)
C9	−0.2687 (4)	0.40917 (10)	0.45077 (17)	0.0420 (5)
H9A	−0.2263	0.4284	0.3846	0.063*
H9B	−0.3793	0.4368	0.4813	0.063*
H9C	−0.3449	0.3683	0.4324	0.063*
C10	0.8718 (3)	0.29097 (11)	0.77813 (16)	0.0409 (5)
H10A	0.9014	0.2485	0.7525	0.061*
H10B	0.8573	0.2894	0.8558	0.061*
H10C	1.0048	0.3186	0.7682	0.061*
C11	0.3393 (3)	0.17417 (8)	0.57532 (14)	0.0282 (4)
H11	0.1729	0.1907	0.5573	0.034*
C12	0.3871 (4)	0.15762 (10)	0.69641 (15)	0.0384 (5)
H12A	0.5537	0.1430	0.7169	0.046*
H12B	0.3656	0.1955	0.7404	0.046*
C13	0.2166 (4)	0.10610 (10)	0.72029 (17)	0.0467 (5)
H13A	0.2528	0.0944	0.7985	0.056*
H13B	0.0510	0.1222	0.7054	0.056*
C14	0.2374 (5)	0.04836 (11)	0.65068 (19)	0.0546 (6)
H14A	0.1200	0.0164	0.6655	0.066*
H14B	0.3986	0.0300	0.6704	0.066*
C15	0.1933 (5)	0.06485 (11)	0.52957 (18)	0.0535 (6)
H15A	0.0263	0.0789	0.5082	0.064*
H15B	0.2170	0.0269	0.4863	0.064*
C16	0.3609 (4)	0.11667 (9)	0.50391 (16)	0.0404 (5)
H16A	0.3208	0.1286	0.4259	0.049*
H16B	0.5271	0.1011	0.5172	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0286 (2)	0.0324 (3)	0.0304 (2)	−0.00048 (19)	0.01150 (18)	0.00121 (18)
O1	0.0377 (7)	0.0379 (8)	0.0304 (7)	−0.0085 (6)	0.0050 (6)	−0.0033 (5)
O2	0.0263 (7)	0.0467 (8)	0.0558 (9)	0.0009 (6)	0.0144 (6)	−0.0012 (7)
O3	0.0541 (9)	0.0373 (8)	0.0276 (7)	0.0000 (6)	0.0145 (6)	0.0025 (5)
C1	0.0302 (10)	0.0312 (10)	0.0289 (9)	−0.0056 (8)	0.0097 (7)	0.0009 (7)
C2	0.0311 (9)	0.0276 (9)	0.0286 (9)	−0.0069 (7)	0.0109 (7)	0.0012 (7)
C3	0.0369 (10)	0.0282 (10)	0.0287 (9)	−0.0060 (8)	0.0085 (8)	−0.0001 (7)
C4	0.0364 (10)	0.0280 (10)	0.0370 (10)	−0.0040 (8)	0.0085 (8)	0.0052 (8)
C5	0.0471 (12)	0.0272 (10)	0.0444 (11)	0.0009 (9)	0.0143 (9)	0.0018 (8)
C6	0.0519 (13)	0.0297 (11)	0.0374 (10)	−0.0061 (9)	0.0110 (9)	−0.0067 (8)
C7	0.0349 (10)	0.0320 (10)	0.0284 (9)	−0.0089 (8)	0.0075 (8)	−0.0001 (7)
C8	0.0332 (10)	0.0365 (11)	0.0319 (9)	−0.0077 (8)	0.0116 (8)	0.0033 (8)
C9	0.0413 (12)	0.0382 (12)	0.0458 (12)	0.0000 (9)	0.0047 (9)	0.0088 (9)
C10	0.0300 (10)	0.0582 (13)	0.0337 (10)	−0.0063 (9)	0.0025 (8)	0.0045 (9)
C11	0.0238 (9)	0.0324 (10)	0.0288 (9)	−0.0015 (7)	0.0052 (7)	0.0025 (7)
C12	0.0437 (11)	0.0430 (12)	0.0286 (9)	−0.0096 (9)	0.0064 (8)	0.0049 (8)
C13	0.0515 (13)	0.0547 (14)	0.0339 (10)	−0.0153 (11)	0.0072 (9)	0.0109 (9)
C14	0.0652 (15)	0.0415 (13)	0.0568 (14)	−0.0163 (11)	0.0088 (12)	0.0121 (10)
C15	0.0713 (16)	0.0432 (13)	0.0471 (12)	−0.0193 (11)	0.0131 (11)	−0.0048 (10)
C16	0.0516 (13)	0.0355 (11)	0.0362 (10)	−0.0057 (9)	0.0133 (9)	−0.0034 (8)

Geometric parameters (Å, º) top

S1—O2	1.4368 (13)	C9—H9C	0.9800
S1—O3	1.4395 (13)	C10—H10A	0.9800
S1—C1	1.7385 (18)	C10—H10B	0.9800
S1—C11	1.7797 (17)	C10—H10C	0.9800
O1—C8	1.369 (2)	C11—C12	1.523 (2)
O1—C7	1.382 (2)	C11—C16	1.525 (3)
C1—C8	1.358 (3)	C11—H11	1.0000
C1—C2	1.443 (3)	C12—C13	1.522 (3)
C2—C7	1.390 (2)	C12—H12A	0.9900
C2—C3	1.391 (3)	C12—H12B	0.9900
C3—C4	1.386 (3)	C13—C14	1.515 (3)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.404 (3)	C13—H13B	0.9900
C4—C9	1.505 (3)	C14—C15	1.522 (3)
C5—C6	1.378 (3)	C14—H14A	0.9900
C5—H5	0.9500	C14—H14B	0.9900
C6—C7	1.375 (3)	C15—C16	1.522 (3)
C6—H6	0.9500	C15—H15A	0.9900
C8—C10	1.477 (3)	C15—H15B	0.9900
C9—H9A	0.9800	C16—H16A	0.9900
C9—H9B	0.9800	C16—H16B	0.9900

O2—S1—O3	118.14 (8)	C8—C10—H10C	109.5
O2—S1—C1	108.80 (9)	H10A—C10—H10C	109.5
O3—S1—C1	107.46 (8)	H10B—C10—H10C	109.5
O2—S1—C11	108.47 (8)	C12—C11—C16	111.65 (16)
O3—S1—C11	107.62 (8)	C12—C11—S1	112.35 (12)
C1—S1—C11	105.67 (8)	C16—C11—S1	107.96 (12)
C8—O1—C7	107.10 (14)	C12—C11—H11	108.2
C8—C1—C2	108.03 (16)	C16—C11—H11	108.2
C8—C1—S1	126.98 (15)	S1—C11—H11	108.2
C2—C1—S1	124.96 (13)	C13—C12—C11	109.85 (16)
C7—C2—C3	118.99 (17)	C13—C12—H12A	109.7
C7—C2—C1	104.56 (16)	C11—C12—H12A	109.7
C3—C2—C1	136.45 (16)	C13—C12—H12B	109.7
C4—C3—C2	119.42 (17)	C11—C12—H12B	109.7
C4—C3—H3	120.3	H12A—C12—H12B	108.2
C2—C3—H3	120.3	C14—C13—C12	111.12 (17)
C3—C4—C5	119.18 (18)	C14—C13—H13A	109.4
C3—C4—C9	120.43 (17)	C12—C13—H13A	109.4
C5—C4—C9	120.39 (18)	C14—C13—H13B	109.4
C6—C5—C4	122.59 (18)	C12—C13—H13B	109.4
C6—C5—H5	118.7	H13A—C13—H13B	108.0
C4—C5—H5	118.7	C13—C14—C15	111.09 (18)
C7—C6—C5	116.34 (18)	C13—C14—H14A	109.4
C7—C6—H6	121.8	C15—C14—H14A	109.4
C5—C6—H6	121.8	C13—C14—H14B	109.4
C6—C7—O1	126.21 (16)	C15—C14—H14B	109.4
C6—C7—C2	123.48 (18)	H14A—C14—H14B	108.0
O1—C7—C2	110.31 (16)	C14—C15—C16	111.32 (18)
C1—C8—O1	110.00 (16)	C14—C15—H15A	109.4
C1—C8—C10	134.80 (19)	C16—C15—H15A	109.4
O1—C8—C10	115.20 (16)	C14—C15—H15B	109.4
C4—C9—H9A	109.5	C16—C15—H15B	109.4
C4—C9—H9B	109.5	H15A—C15—H15B	108.0
H9A—C9—H9B	109.5	C15—C16—C11	110.25 (16)
C4—C9—H9C	109.5	C15—C16—H16A	109.6
H9A—C9—H9C	109.5	C11—C16—H16A	109.6
H9B—C9—H9C	109.5	C15—C16—H16B	109.6
C8—C10—H10A	109.5	C11—C16—H16B	109.6
C8—C10—H10B	109.5	H16A—C16—H16B	108.1
H10A—C10—H10B	109.5

O2—S1—C1—C8	−13.71 (19)	C3—C2—C7—O1	179.92 (14)
O3—S1—C1—C8	−142.70 (16)	C1—C2—C7—O1	0.39 (18)
C11—S1—C1—C8	102.59 (17)	C2—C1—C8—O1	−0.52 (19)
O2—S1—C1—C2	164.31 (14)	S1—C1—C8—O1	177.76 (12)
O3—S1—C1—C2	35.31 (17)	C2—C1—C8—C10	179.59 (19)
C11—S1—C1—C2	−79.39 (16)	S1—C1—C8—C10	−2.1 (3)
C8—C1—C2—C7	0.08 (18)	C7—O1—C8—C1	0.76 (19)
S1—C1—C2—C7	−178.25 (13)	C7—O1—C8—C10	−179.33 (15)
C8—C1—C2—C3	−179.33 (19)	O2—S1—C11—C12	59.13 (15)
S1—C1—C2—C3	2.3 (3)	O3—S1—C11—C12	−171.99 (13)
C7—C2—C3—C4	−0.5 (2)	C1—S1—C11—C12	−57.40 (15)
C1—C2—C3—C4	178.88 (18)	O2—S1—C11—C16	−64.43 (15)
C2—C3—C4—C5	−0.2 (3)	O3—S1—C11—C16	64.46 (14)
C2—C3—C4—C9	179.96 (16)	C1—S1—C11—C16	179.05 (13)
C3—C4—C5—C6	0.7 (3)	C16—C11—C12—C13	−57.1 (2)
C9—C4—C5—C6	−179.43 (18)	S1—C11—C12—C13	−178.58 (14)
C4—C5—C6—C7	−0.6 (3)	C11—C12—C13—C14	56.9 (2)
C5—C6—C7—O1	−179.30 (16)	C12—C13—C14—C15	−56.7 (2)
C5—C6—C7—C2	−0.2 (3)	C13—C14—C15—C16	55.8 (3)
C8—O1—C7—C6	178.52 (17)	C14—C15—C16—C11	−55.3 (3)
C8—O1—C7—C2	−0.71 (18)	C12—C11—C16—C15	56.4 (2)
C3—C2—C7—C6	0.7 (3)	S1—C11—C16—C15	−179.62 (15)
C1—C2—C7—C6	−178.87 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	1.00	2.31	3.273 (2)	161
C12—H12B···O3ⁱⁱ	0.99	2.57	3.443 (2)	146
C10—H10C···Cgⁱⁱⁱ	0.99	2.75	3.556 (2)	140

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀O₃S
M_r	292.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	5.6854 (3), 21.2391 (13), 12.3944 (7)
β (°)	99.295 (3)
V (Å³)	1477.01 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.643, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13128, 3228, 2477
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.05
No. of reflections	3228
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.34

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

Cg is the centroid of the C2–C7 benzene ring

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	1.00	2.31	3.273 (2)	161
C12—H12B···O3ⁱⁱ	0.99	2.57	3.443 (2)	146
C10—H10C···Cgⁱⁱⁱ	0.99	2.75	3.556 (2)	140

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

Acknowledgements

This work was supported by Dong-eui University (grant No. 2011AA098).

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