3-(3-Fluoro­phenyl­sulfin­yl)-2,4,6,7-tetra­methyl-1-benzofuran

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

doi:10.1107/S1600536811016102

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1323

doi:10.1107/S1600536811016102

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3-(3-Fluorophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^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 18 April 2011; accepted 28 April 2011; online 7 May 2011)

In the title compound, C₁₈H₁₇FO₂S, the 3-fluorophenyl ring makes a dihedral angle of 78.30 (5)° 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 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ,b ).

Experimental

Crystal data

C₁₈H₁₇FO₂S
M_r = 316.38
Triclinic, $[P \overline 1]$
a = 7.2690 (2) Å
b = 8.0039 (3) Å
c = 13.7968 (5) Å
α = 76.839 (1)°
β = 88.561 (1)°
γ = 77.506 (1)°
V = 762.86 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.29 × 0.24 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.936, T_max = 0.979
13783 measured reflections
3520 independent reflections
2958 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 1.05
3520 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 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
C12—H12C⋯O2ⁱ	0.98	2.34	3.295 (2)	165
C10—H10A⋯Cgⁱⁱ	0.98	2.74	3.547 (2)	141
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -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 (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/S1600536811016102/zq2099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016102/zq2099Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016102/zq2099Isup3.cml

checkCIF report

Comment top

A series of benzofuran ring system show interesting 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 study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.016 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring makes a dihedral angle of 78.30 (5)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a methyl H atom and the O atom of the sulfinyl group (Table 1; C12—H12C···O2ⁱ). The crystal structure is further stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C10—H10A···Cgⁱⁱ, Cg being 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 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-2,4,6,7-tetramethyl-1-benzofuran (360 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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 79%, m.p. 413–414 K; R _f = 0.58 (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 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 (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 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 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 + 1, - y + 1, - z + 1; (iii) x + 1, y, z]

3-(3-Fluorophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran top

Crystal data top

C₁₈H₁₇FO₂S	Z = 2
M_r = 316.38	F(000) = 332
Triclinic, P1	D_x = 1.377 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2690 (2) Å	Cell parameters from 4445 reflections
b = 8.0039 (3) Å	θ = 2.7–27.1°
c = 13.7968 (5) Å	µ = 0.23 mm⁻¹
α = 76.839 (1)°	T = 173 K
β = 88.561 (1)°	Block, colourless
γ = 77.506 (1)°	0.29 × 0.24 × 0.09 mm
V = 762.86 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3520 independent reflections
Radiation source: rotating anode	2958 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→10
T_min = 0.936, T_max = 0.979	l = −17→17
13783 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0482P)² + 0.326P] where P = (F_o² + 2F_c²)/3
3520 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₇FO₂S	γ = 77.506 (1)°
M_r = 316.38	V = 762.86 (4) Å³
Triclinic, P1	Z = 2
a = 7.2690 (2) Å	Mo Kα radiation
b = 8.0039 (3) Å	µ = 0.23 mm⁻¹
c = 13.7968 (5) Å	T = 173 K
α = 76.839 (1)°	0.29 × 0.24 × 0.09 mm
β = 88.561 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3520 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2958 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.979	R_int = 0.032
13783 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	Δρ_max = 0.35 e Å⁻³
3520 reflections	Δρ_min = −0.30 e Å⁻³
203 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	0.60154 (6)	0.80711 (5)	0.84314 (3)	0.02726 (13)
F1	0.4058 (2)	0.21849 (18)	0.90810 (10)	0.0677 (4)
O1	0.24868 (15)	0.91394 (15)	0.61908 (8)	0.0268 (3)
O2	0.78749 (17)	0.85793 (17)	0.83599 (10)	0.0368 (3)
C1	0.4973 (2)	0.8378 (2)	0.72511 (11)	0.0242 (3)
C2	0.5606 (2)	0.7783 (2)	0.63519 (11)	0.0231 (3)
C3	0.7296 (2)	0.6944 (2)	0.59983 (12)	0.0258 (3)
C4	0.7203 (2)	0.6631 (2)	0.50521 (12)	0.0280 (3)
H4	0.8330	0.6070	0.4791	0.034*
C5	0.5554 (2)	0.7087 (2)	0.44574 (12)	0.0268 (3)
C6	0.3874 (2)	0.7954 (2)	0.47974 (12)	0.0256 (3)
C7	0.4001 (2)	0.8278 (2)	0.57324 (12)	0.0240 (3)
C8	0.3124 (2)	0.9188 (2)	0.71057 (12)	0.0263 (3)
C9	0.9120 (2)	0.6381 (3)	0.65882 (13)	0.0341 (4)
H9A	0.9155	0.7190	0.7021	0.051*
H9B	1.0176	0.6398	0.6132	0.051*
H9C	0.9222	0.5189	0.6996	0.051*
C10	0.5592 (3)	0.6614 (2)	0.34618 (13)	0.0337 (4)
H10A	0.4829	0.5736	0.3482	0.050*
H10B	0.6894	0.6129	0.3308	0.050*
H10C	0.5076	0.7668	0.2947	0.050*
C11	0.2058 (2)	0.8485 (2)	0.42018 (13)	0.0332 (4)
H11A	0.1065	0.9088	0.4573	0.050*
H11B	0.1705	0.7437	0.4077	0.050*
H11C	0.2219	0.9279	0.3565	0.050*
C12	0.1714 (2)	1.0080 (3)	0.77179 (14)	0.0346 (4)
H12A	0.1189	1.1283	0.7348	0.052*
H12B	0.2320	1.0110	0.8338	0.052*
H12C	0.0700	0.9437	0.7873	0.052*
C13	0.6508 (2)	0.5703 (2)	0.87613 (12)	0.0290 (4)
C14	0.5051 (3)	0.4843 (2)	0.87530 (12)	0.0346 (4)
H14	0.3813	0.5471	0.8532	0.042*
C15	0.5468 (3)	0.3042 (3)	0.90778 (13)	0.0441 (5)
C16	0.7232 (4)	0.2093 (3)	0.94023 (15)	0.0532 (6)
H16	0.7472	0.0848	0.9612	0.064*
C17	0.8648 (3)	0.2981 (3)	0.94177 (16)	0.0540 (6)
H17	0.9879	0.2346	0.9646	0.065*
C18	0.8292 (3)	0.4799 (3)	0.91021 (14)	0.0395 (4)
H18	0.9269	0.5412	0.9121	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0301 (2)	0.0285 (2)	0.0260 (2)	−0.00976 (16)	−0.00194 (15)	−0.00842 (16)
F1	0.1098 (12)	0.0561 (8)	0.0512 (8)	−0.0541 (8)	−0.0068 (7)	−0.0057 (6)
O1	0.0239 (5)	0.0294 (6)	0.0277 (6)	−0.0050 (4)	−0.0006 (4)	−0.0080 (5)
O2	0.0341 (6)	0.0403 (7)	0.0420 (7)	−0.0173 (6)	−0.0034 (5)	−0.0121 (6)
C1	0.0258 (7)	0.0234 (8)	0.0245 (8)	−0.0078 (6)	−0.0007 (6)	−0.0050 (6)
C2	0.0266 (7)	0.0191 (7)	0.0236 (7)	−0.0075 (6)	−0.0003 (6)	−0.0026 (6)
C3	0.0264 (8)	0.0219 (8)	0.0287 (8)	−0.0064 (6)	−0.0001 (6)	−0.0040 (6)
C4	0.0291 (8)	0.0237 (8)	0.0306 (8)	−0.0050 (6)	0.0039 (6)	−0.0063 (7)
C5	0.0347 (8)	0.0221 (8)	0.0246 (8)	−0.0101 (6)	0.0016 (6)	−0.0038 (6)
C6	0.0299 (8)	0.0215 (8)	0.0251 (8)	−0.0082 (6)	−0.0027 (6)	−0.0016 (6)
C7	0.0243 (7)	0.0204 (7)	0.0264 (8)	−0.0057 (6)	0.0013 (6)	−0.0031 (6)
C8	0.0276 (8)	0.0262 (8)	0.0273 (8)	−0.0101 (6)	0.0005 (6)	−0.0062 (6)
C9	0.0256 (8)	0.0397 (10)	0.0354 (9)	−0.0007 (7)	−0.0017 (7)	−0.0112 (8)
C10	0.0421 (10)	0.0331 (10)	0.0283 (9)	−0.0109 (8)	0.0018 (7)	−0.0097 (7)
C11	0.0341 (9)	0.0362 (10)	0.0292 (9)	−0.0081 (7)	−0.0062 (7)	−0.0058 (7)
C12	0.0271 (8)	0.0435 (11)	0.0365 (9)	−0.0073 (7)	0.0025 (7)	−0.0162 (8)
C13	0.0397 (9)	0.0287 (9)	0.0195 (7)	−0.0090 (7)	−0.0013 (6)	−0.0055 (6)
C14	0.0468 (10)	0.0362 (10)	0.0243 (8)	−0.0163 (8)	−0.0020 (7)	−0.0069 (7)
C15	0.0786 (15)	0.0390 (11)	0.0243 (9)	−0.0312 (10)	0.0018 (9)	−0.0094 (8)
C16	0.0924 (18)	0.0281 (10)	0.0355 (11)	−0.0065 (11)	−0.0036 (11)	−0.0056 (8)
C17	0.0620 (14)	0.0423 (12)	0.0468 (12)	0.0052 (10)	−0.0067 (10)	−0.0028 (10)
C18	0.0415 (10)	0.0403 (11)	0.0340 (10)	−0.0055 (8)	−0.0040 (8)	−0.0053 (8)

Geometric parameters (Å, º) top

S1—O2	1.4883 (12)	C9—H9C	0.9800
S1—C1	1.7565 (16)	C10—H10A	0.9800
S1—C13	1.8024 (18)	C10—H10B	0.9800
F1—C15	1.351 (2)	C10—H10C	0.9800
O1—C8	1.3670 (19)	C11—H11A	0.9800
O1—C7	1.3862 (18)	C11—H11B	0.9800
C1—C8	1.358 (2)	C11—H11C	0.9800
C1—C2	1.457 (2)	C12—H12A	0.9800
C2—C7	1.395 (2)	C12—H12B	0.9800
C2—C3	1.400 (2)	C12—H12C	0.9800
C3—C4	1.390 (2)	C13—C18	1.377 (3)
C3—C9	1.501 (2)	C13—C14	1.384 (2)
C4—C5	1.402 (2)	C14—C15	1.377 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.395 (2)	C15—C16	1.369 (3)
C5—C10	1.504 (2)	C16—C17	1.374 (3)
C6—C7	1.382 (2)	C16—H16	0.9500
C6—C11	1.500 (2)	C17—C18	1.389 (3)
C8—C12	1.479 (2)	C17—H17	0.9500
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800

O2—S1—C1	111.73 (7)	C5—C10—H10B	109.5
O2—S1—C13	106.34 (8)	H10A—C10—H10B	109.5
C1—S1—C13	98.05 (7)	C5—C10—H10C	109.5
C8—O1—C7	106.92 (12)	H10A—C10—H10C	109.5
C8—C1—C2	107.56 (14)	H10B—C10—H10C	109.5
C8—C1—S1	118.37 (12)	C6—C11—H11A	109.5
C2—C1—S1	133.75 (12)	C6—C11—H11B	109.5
C7—C2—C3	118.54 (14)	H11A—C11—H11B	109.5
C7—C2—C1	104.30 (13)	C6—C11—H11C	109.5
C3—C2—C1	137.14 (14)	H11A—C11—H11C	109.5
C4—C3—C2	116.01 (14)	H11B—C11—H11C	109.5
C4—C3—C9	120.60 (15)	C8—C12—H12A	109.5
C2—C3—C9	123.38 (15)	C8—C12—H12B	109.5
C3—C4—C5	124.32 (15)	H12A—C12—H12B	109.5
C3—C4—H4	117.8	C8—C12—H12C	109.5
C5—C4—H4	117.8	H12A—C12—H12C	109.5
C6—C5—C4	119.95 (15)	H12B—C12—H12C	109.5
C6—C5—C10	120.06 (15)	C18—C13—C14	121.39 (17)
C4—C5—C10	119.98 (15)	C18—C13—S1	119.02 (14)
C7—C6—C5	114.88 (14)	C14—C13—S1	119.32 (14)
C7—C6—C11	122.22 (15)	C15—C14—C13	117.24 (18)
C5—C6—C11	122.90 (15)	C15—C14—H14	121.4
C6—C7—O1	123.28 (14)	C13—C14—H14	121.4
C6—C7—C2	126.23 (15)	F1—C15—C16	118.97 (19)
O1—C7—C2	110.48 (13)	F1—C15—C14	117.9 (2)
C1—C8—O1	110.73 (14)	C16—C15—C14	123.1 (2)
C1—C8—C12	133.72 (15)	C15—C16—C17	118.52 (19)
O1—C8—C12	115.56 (14)	C15—C16—H16	120.7
C3—C9—H9A	109.5	C17—C16—H16	120.7
C3—C9—H9B	109.5	C16—C17—C18	120.5 (2)
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
C5—C10—H10A	109.5	C17—C18—H18	120.4

O2—S1—C1—C8	−133.77 (13)	C8—O1—C7—C2	−0.24 (17)
C13—S1—C1—C8	115.00 (14)	C3—C2—C7—C6	3.1 (2)
O2—S1—C1—C2	53.79 (18)	C1—C2—C7—C6	−178.02 (15)
C13—S1—C1—C2	−57.45 (17)	C3—C2—C7—O1	−177.96 (13)
C8—C1—C2—C7	−1.30 (17)	C1—C2—C7—O1	0.94 (17)
S1—C1—C2—C7	171.73 (13)	C2—C1—C8—O1	1.22 (18)
C8—C1—C2—C3	177.28 (18)	S1—C1—C8—O1	−173.06 (10)
S1—C1—C2—C3	−9.7 (3)	C2—C1—C8—C12	−178.76 (18)
C7—C2—C3—C4	−1.8 (2)	S1—C1—C8—C12	7.0 (3)
C1—C2—C3—C4	179.78 (17)	C7—O1—C8—C1	−0.64 (17)
C7—C2—C3—C9	178.81 (15)	C7—O1—C8—C12	179.35 (14)
C1—C2—C3—C9	0.4 (3)	O2—S1—C13—C18	14.28 (16)
C2—C3—C4—C5	−0.4 (2)	C1—S1—C13—C18	129.83 (15)
C9—C3—C4—C5	179.01 (16)	O2—S1—C13—C14	−171.55 (13)
C3—C4—C5—C6	1.7 (3)	C1—S1—C13—C14	−56.01 (14)
C3—C4—C5—C10	−177.23 (15)	C18—C13—C14—C15	−1.5 (3)
C4—C5—C6—C7	−0.5 (2)	S1—C13—C14—C15	−175.51 (13)
C10—C5—C6—C7	178.34 (14)	C13—C14—C15—F1	179.53 (15)
C4—C5—C6—C11	179.90 (15)	C13—C14—C15—C16	0.1 (3)
C10—C5—C6—C11	−1.2 (2)	F1—C15—C16—C17	−178.53 (18)
C5—C6—C7—O1	179.35 (14)	C14—C15—C16—C17	0.9 (3)
C11—C6—C7—O1	−1.1 (2)	C15—C16—C17—C18	−0.5 (3)
C5—C6—C7—C2	−1.8 (2)	C14—C13—C18—C17	1.8 (3)
C11—C6—C7—C2	177.74 (15)	S1—C13—C18—C17	175.89 (15)
C8—O1—C7—C6	178.75 (14)	C16—C17—C18—C13	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid ofthe C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O2ⁱ	0.98	2.34	3.295 (2)	165
C10—H10A···Cgⁱⁱ	0.98	2.74	3.547 (2)	141

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇FO₂S
M_r	316.38
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.2690 (2), 8.0039 (3), 13.7968 (5)
α, β, γ (°)	76.839 (1), 88.561 (1), 77.506 (1)
V (Å³)	762.86 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.29 × 0.24 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.936, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	13783, 3520, 2958
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.05
No. of reflections	3520
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.30

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 ofthe C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O2ⁱ	0.98	2.34	3.295 (2)	164.9
C10—H10A···Cgⁱⁱ	0.98	2.74	3.547 (2)	140.5

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

References

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Volume 67| Part 6| June 2011| Page o1323

doi:10.1107/S1600536811016102

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