2,4,5,6-Tetra­methyl-3-phenyl­sulfinyl-1-benzofuran

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811018952

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1512

doi:10.1107/S1600536811018952

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2,4,5,6-Tetramethyl-3-phenylsulfinyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^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 3 May 2011; accepted 19 May 2011; online 25 May 2011)

In the title compound, C₁₈H₁₈O₂S, the phenyl ring makes a dihedral angle of 87.47 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological 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 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2008a ,b ,c ).

Experimental

Crystal data

C₁₈H₁₈O₂S
M_r = 298.38
Monoclinic, P 2₁ /c
a = 14.2611 (5) Å
b = 6.0661 (2) Å
c = 17.2436 (7) Å
β = 99.740 (2)°
V = 1470.23 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.29 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.622, T_max = 0.746
25036 measured reflections
3397 independent reflections
2888 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.155
S = 1.04
3397 reflections
188 parameters
H-atom parameters constrained
Δρ_max = 1.20 e Å⁻³
Δρ_min = −0.56 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
C6—H6⋯O2ⁱ	0.95	2.35	3.286 (3)	169
C10—H10A⋯O2ⁱⁱ	0.98	2.56	3.517 (3)	167
C12—H12C⋯Cgⁱⁱⁱ	0.98	2.66	3.482 (3)	142
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) x, 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 (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/S1600536811018952/jj2090sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018952/jj2090Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018952/jj2090Isup3.cml

checkCIF report

Comment top

Recently, a series of compounds containing the benzofuran ring system have been shown to exhibit significant pharmacological properties such as antibacterial, antifungal, antitumor, antiviral, and antimicrobial activities (Aslam et al. , 2009, Galal et al. , 2009, Khan et al. , 2005). These types of compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al. , 2003). As a part of our study of the substituent effect on the solid state structures of 2-methyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2008a,b,c), we report hrerin the crystal structure of the title compound, C₁₈H₁₈O₂S.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.017 (1) Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring makes a dihedral angle of 87.47 (6)° with the mean plane of the benzofuran fragment. Crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1 & Fig. 2) and weak C—H···Cg π–ring interactions (Table 1 & Fig 3; Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the biological 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 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2008a,b,c).

Experimental top

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2,4,5,6-tetramethyl-3-phenylsulfanyl-1-benzofuran (310 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 438–439 K; R_f = 0.51 (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 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 (Bruker, 2009).

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 a small spheres of arbitrary radius.
	Fig. 2. A view of the weak C—H···O interactions (dotted lines) in the crystal packing of the title compound. [Symmetry codes: (i) x, - y + 1/2 , z - 1/2; (ii) - x, - y + 1, - z + 1; (iv) x, - y + 1/2, z + 1/2.]
	Fig. 3. A view of the weak C—H···Cg π-ring intermolecular interactions (dotted lines) in the crystal packing of the title compound. [Symmetry codes: (iii) x, y - 1, z.]

2,4,5,6-Tetramethyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₁₈H₁₈O₂S	F(000) = 632
M_r = 298.38	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7044 reflections
a = 14.2611 (5) Å	θ = 2.4–27.5°
b = 6.0661 (2) Å	µ = 0.22 mm⁻¹
c = 17.2436 (7) Å	T = 173 K
β = 99.740 (2)°	Block, colourless
V = 1470.23 (9) Å³	0.29 × 0.20 × 0.14 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3397 independent reflections
Radiation source: rotating anode	2888 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.050
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.6°, θ_min = 1.5°
ϕ and ω scans	h = −18→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −7→7
T_min = 0.622, T_max = 0.746	l = −22→22
25036 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)] = 0.058	Hydrogen site location: difference Fourier map
wR(F²) = 0.155	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0691P)² + 1.9351P] where P = (F_o² + 2F_c²)/3
3397 reflections	(Δ/σ)_max = 0.001
188 parameters	Δρ_max = 1.20 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₈H₁₈O₂S	V = 1470.23 (9) Å³
M_r = 298.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2611 (5) Å	µ = 0.22 mm⁻¹
b = 6.0661 (2) Å	T = 173 K
c = 17.2436 (7) Å	0.29 × 0.20 × 0.14 mm
β = 99.740 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3397 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2888 reflections with I > 2σ(I)
T_min = 0.622, T_max = 0.746	R_int = 0.050
25036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.04	Δρ_max = 1.20 e Å⁻³
3397 reflections	Δρ_min = −0.56 e Å⁻³
188 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	0.28526 (4)	0.15501 (10)	0.58076 (4)	0.03155 (19)
O1	0.27241 (11)	0.1859 (3)	0.35463 (10)	0.0271 (4)
O2	0.19888 (14)	0.1527 (3)	0.61794 (11)	0.0420 (5)
C1	0.25752 (15)	0.2287 (4)	0.48136 (13)	0.0251 (5)
C2	0.20419 (15)	0.4077 (3)	0.43714 (12)	0.0219 (4)
C3	0.14688 (15)	0.5842 (4)	0.45266 (12)	0.0225 (4)
C4	0.10995 (15)	0.7234 (4)	0.39007 (13)	0.0233 (4)
C5	0.12764 (15)	0.6842 (4)	0.31306 (13)	0.0239 (4)
C6	0.18162 (15)	0.5044 (4)	0.29734 (13)	0.0245 (5)
H6	0.1930	0.4739	0.2457	0.029*
C7	0.21775 (15)	0.3723 (3)	0.36019 (13)	0.0230 (4)
C8	0.29453 (16)	0.1033 (4)	0.42877 (14)	0.0275 (5)
C9	0.12387 (18)	0.6209 (4)	0.53373 (14)	0.0302 (5)
H9A	0.1379	0.4866	0.5651	0.045*
H9B	0.0563	0.6572	0.5297	0.045*
H9C	0.1624	0.7428	0.5592	0.045*
C10	0.04905 (17)	0.9172 (4)	0.40466 (15)	0.0317 (5)
H10A	−0.0180	0.8728	0.3956	0.048*
H10B	0.0581	1.0374	0.3687	0.048*
H10C	0.0675	0.9672	0.4591	0.048*
C11	0.08671 (18)	0.8332 (4)	0.24575 (14)	0.0320 (5)
H11A	0.1034	0.7760	0.1967	0.048*
H11B	0.1128	0.9819	0.2555	0.048*
H11C	0.0173	0.8384	0.2413	0.048*
C12	0.35458 (14)	−0.0982 (3)	0.43559 (11)	0.0378 (6)
H12A	0.3646	−0.1510	0.4901	0.057*
H12B	0.4162	−0.0636	0.4205	0.057*
H12C	0.3226	−0.2129	0.4007	0.057*
C13	0.35299 (11)	0.3951 (3)	0.61796 (9)	0.0275 (5)
C14	0.43833 (10)	0.4325 (2)	0.59220 (10)	0.0327 (5)
H14	0.4567	0.3431	0.5521	0.039*
C15	0.49648 (19)	0.6014 (5)	0.62557 (17)	0.0423 (7)
H15	0.5556	0.6278	0.6088	0.051*
C16	0.4686 (2)	0.7322 (5)	0.68343 (17)	0.0456 (7)
H16	0.5083	0.8495	0.7059	0.055*
C17	0.3838 (2)	0.6929 (5)	0.70828 (17)	0.0452 (7)
H17	0.3647	0.7840	0.7476	0.054*
C18	0.32583 (18)	0.5214 (5)	0.67638 (15)	0.0370 (6)
H18	0.2679	0.4914	0.6947	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0337 (3)	0.0300 (3)	0.0297 (3)	−0.0058 (2)	0.0016 (2)	0.0081 (2)
O1	0.0258 (8)	0.0250 (8)	0.0309 (9)	0.0009 (6)	0.0059 (7)	−0.0045 (6)
O2	0.0397 (10)	0.0523 (12)	0.0347 (10)	−0.0122 (9)	0.0086 (8)	0.0101 (8)
C1	0.0245 (11)	0.0244 (10)	0.0256 (11)	−0.0046 (8)	0.0017 (8)	0.0033 (8)
C2	0.0219 (10)	0.0221 (10)	0.0213 (10)	−0.0044 (8)	0.0024 (8)	0.0005 (8)
C3	0.0207 (10)	0.0256 (10)	0.0217 (10)	−0.0055 (8)	0.0052 (8)	−0.0042 (8)
C4	0.0194 (10)	0.0244 (10)	0.0269 (11)	−0.0021 (8)	0.0062 (8)	−0.0016 (8)
C5	0.0204 (10)	0.0266 (10)	0.0238 (11)	−0.0028 (8)	0.0017 (8)	0.0010 (8)
C6	0.0252 (11)	0.0294 (11)	0.0194 (10)	−0.0028 (8)	0.0049 (8)	−0.0032 (8)
C7	0.0200 (10)	0.0226 (10)	0.0264 (11)	−0.0017 (8)	0.0037 (8)	−0.0051 (8)
C8	0.0225 (11)	0.0236 (10)	0.0355 (12)	−0.0035 (8)	0.0025 (9)	0.0002 (9)
C9	0.0330 (12)	0.0349 (12)	0.0245 (11)	−0.0019 (9)	0.0102 (9)	−0.0039 (9)
C10	0.0283 (12)	0.0305 (12)	0.0373 (13)	0.0050 (9)	0.0085 (10)	−0.0017 (10)
C11	0.0336 (13)	0.0339 (12)	0.0274 (12)	0.0009 (10)	0.0017 (10)	0.0054 (10)
C12	0.0329 (13)	0.0263 (12)	0.0535 (16)	0.0031 (10)	0.0051 (12)	0.0010 (11)
C13	0.0255 (11)	0.0303 (11)	0.0249 (11)	−0.0017 (9)	−0.0013 (9)	0.0069 (9)
C14	0.0273 (12)	0.0362 (13)	0.0342 (13)	−0.0013 (10)	0.0041 (10)	0.0017 (10)
C15	0.0318 (14)	0.0471 (16)	0.0460 (16)	−0.0116 (11)	0.0011 (12)	0.0062 (12)
C16	0.0509 (17)	0.0362 (14)	0.0429 (16)	−0.0085 (12)	−0.0119 (13)	0.0010 (12)
C17	0.0554 (18)	0.0440 (15)	0.0322 (14)	0.0096 (13)	−0.0046 (12)	−0.0070 (12)
C18	0.0327 (13)	0.0504 (15)	0.0271 (12)	0.0049 (11)	0.0024 (10)	0.0034 (11)

Geometric parameters (Å, º) top

S1—O2	1.482 (2)	C10—H10A	0.9800
S1—C1	1.751 (2)	C10—H10B	0.9800
S1—C13	1.8046 (18)	C10—H10C	0.9800
O1—C8	1.359 (3)	C11—H11A	0.9800
O1—C7	1.386 (3)	C11—H11B	0.9800
C1—C8	1.357 (3)	C11—H11C	0.9800
C1—C2	1.463 (3)	C12—H12A	0.9800
C2—C7	1.390 (3)	C12—H12B	0.9800
C2—C3	1.400 (3)	C12—H12C	0.9800
C3—C4	1.401 (3)	C13—C18	1.372 (3)
C3—C9	1.506 (3)	C13—C14	1.3830
C4—C5	1.413 (3)	C14—C15	1.381 (3)
C4—C10	1.508 (3)	C14—H14	0.9500
C5—C6	1.388 (3)	C15—C16	1.385 (4)
C5—C11	1.508 (3)	C15—H15	0.9500
C6—C7	1.376 (3)	C16—C17	1.370 (5)
C6—H6	0.9500	C16—H16	0.9500
C8—C12	1.486 (3)	C17—C18	1.384 (4)
C9—H9A	0.9800	C17—H17	0.9500
C9—H9B	0.9800	C18—H18	0.9500
C9—H9C	0.9800

O2—S1—C1	111.05 (11)	C4—C10—H10B	109.5
O2—S1—C13	106.72 (10)	H10A—C10—H10B	109.5
C1—S1—C13	99.25 (9)	C4—C10—H10C	109.5
C8—O1—C7	106.22 (17)	H10A—C10—H10C	109.5
C8—C1—C2	107.1 (2)	H10B—C10—H10C	109.5
C8—C1—S1	117.52 (18)	C5—C11—H11A	109.5
C2—C1—S1	135.31 (18)	C5—C11—H11B	109.5
C7—C2—C3	118.7 (2)	H11A—C11—H11B	109.5
C7—C2—C1	103.83 (19)	C5—C11—H11C	109.5
C3—C2—C1	137.4 (2)	H11A—C11—H11C	109.5
C2—C3—C4	117.98 (19)	H11B—C11—H11C	109.5
C2—C3—C9	121.1 (2)	C8—C12—H12A	109.5
C4—C3—C9	120.9 (2)	C8—C12—H12B	109.5
C3—C4—C5	121.3 (2)	H12A—C12—H12B	109.5
C3—C4—C10	119.6 (2)	C8—C12—H12C	109.5
C5—C4—C10	119.2 (2)	H12A—C12—H12C	109.5
C6—C5—C4	120.6 (2)	H12B—C12—H12C	109.5
C6—C5—C11	118.4 (2)	C18—C13—C14	121.16 (15)
C4—C5—C11	121.0 (2)	C18—C13—S1	120.72 (16)
C7—C6—C5	116.7 (2)	C14—C13—S1	117.72 (6)
C7—C6—H6	121.6	C15—C14—C13	119.12 (16)
C5—C6—H6	121.6	C15—C14—H14	120.4
C6—C7—O1	124.1 (2)	C13—C14—H14	120.4
C6—C7—C2	124.6 (2)	C14—C15—C16	120.0 (2)
O1—C7—C2	111.25 (19)	C14—C15—H15	120.0
C1—C8—O1	111.6 (2)	C16—C15—H15	120.0
C1—C8—C12	133.8 (2)	C17—C16—C15	120.1 (3)
O1—C8—C12	114.61 (19)	C17—C16—H16	119.9
C3—C9—H9A	109.5	C15—C16—H16	119.9
C3—C9—H9B	109.5	C16—C17—C18	120.4 (3)
H9A—C9—H9B	109.5	C16—C17—H17	119.8
C3—C9—H9C	109.5	C18—C17—H17	119.8
H9A—C9—H9C	109.5	C13—C18—C17	119.2 (2)
H9B—C9—H9C	109.5	C13—C18—H18	120.4
C4—C10—H10A	109.5	C17—C18—H18	120.4

O2—S1—C1—C8	−132.93 (19)	C8—O1—C7—C6	179.6 (2)
C13—S1—C1—C8	115.04 (18)	C8—O1—C7—C2	−0.6 (2)
O2—S1—C1—C2	50.2 (3)	C3—C2—C7—C6	2.6 (3)
C13—S1—C1—C2	−61.8 (2)	C1—C2—C7—C6	−178.8 (2)
C8—C1—C2—C7	−1.7 (2)	C3—C2—C7—O1	−177.22 (18)
S1—C1—C2—C7	175.39 (19)	C1—C2—C7—O1	1.4 (2)
C8—C1—C2—C3	176.5 (2)	C2—C1—C8—O1	1.4 (2)
S1—C1—C2—C3	−6.4 (4)	S1—C1—C8—O1	−176.26 (14)
C7—C2—C3—C4	−3.2 (3)	C2—C1—C8—C12	179.9 (2)
C1—C2—C3—C4	178.8 (2)	S1—C1—C8—C12	2.2 (4)
C7—C2—C3—C9	175.6 (2)	C7—O1—C8—C1	−0.6 (2)
C1—C2—C3—C9	−2.4 (4)	C7—O1—C8—C12	−179.34 (18)
C2—C3—C4—C5	1.7 (3)	O2—S1—C13—C18	6.54 (19)
C9—C3—C4—C5	−177.1 (2)	C1—S1—C13—C18	121.94 (17)
C2—C3—C4—C10	−179.1 (2)	O2—S1—C13—C14	179.34 (9)
C9—C3—C4—C10	2.1 (3)	C1—S1—C13—C14	−65.26 (9)
C3—C4—C5—C6	0.7 (3)	C18—C13—C14—C15	−0.62 (19)
C10—C4—C5—C6	−178.5 (2)	S1—C13—C14—C15	−173.38 (18)
C3—C4—C5—C11	179.3 (2)	C13—C14—C15—C16	−0.7 (3)
C10—C4—C5—C11	0.1 (3)	C14—C15—C16—C17	0.7 (4)
C4—C5—C6—C7	−1.4 (3)	C15—C16—C17—C18	0.6 (4)
C11—C5—C6—C7	180.0 (2)	C14—C13—C18—C17	1.9 (3)
C5—C6—C7—O1	179.54 (19)	S1—C13—C18—C17	174.44 (19)
C5—C6—C7—C2	−0.3 (3)	C16—C17—C18—C13	−1.9 (4)

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
C6—H6···O2ⁱ	0.95	2.35	3.286 (3)	169
C10—H10A···O2ⁱⁱ	0.98	2.56	3.517 (3)	167
C12—H12C···Cgⁱⁱⁱ	0.98	2.66	3.482 (3)	142

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₂S
M_r	298.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.2611 (5), 6.0661 (2), 17.2436 (7)
β (°)	99.740 (2)
V (Å³)	1470.23 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.29 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.622, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	25036, 3397, 2888
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.155, 1.04
No. of reflections	3397
No. of parameters	188
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.20, −0.56

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXL97 (Bruker, 2009).

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
C6—H6···O2ⁱ	0.95	2.35	3.286 (3)	169.1
C10—H10A···O2ⁱⁱ	0.98	2.56	3.517 (3)	166.9
C12—H12C···Cgⁱⁱⁱ	0.98	2.66	3.482 (3)	141.8

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

References

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Volume 67| Part 6| June 2011| Page o1512

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