5-Cyclo­hexyl-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536812008343

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o944

doi:10.1107/S1600536812008343

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5-Cyclohexyl-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^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

(Received 20 February 2012; accepted 24 February 2012; online 3 March 2012)

In the title compound, C₂₁H₂₁FO₂S, the cyclohexyl ring adopts a chair conformation. The 3-fluorophenyl ring makes a dihedral angle of 38.38 (6)° with the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011a ,b ).

Experimental

Crystal data

C₂₁H₂₁FO₂S
M_r = 356.44
Orthorhombic, P n a 2₁
a = 12.7767 (10) Å
b = 13.0764 (10) Å
c = 10.7711 (8) Å
V = 1799.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.34 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.935, T_max = 0.961
17893 measured reflections
4503 independent reflections
4036 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.096
S = 1.03
4503 reflections
227 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 2131 Friedel pairs
Flack parameter: −0.07 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21B⋯O2ⁱ	0.98	2.30	3.276 (3)	176
Symmetry code: (i) $[-x+1, -y, z-{\script{1\over 2}}]$ .

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/S1600536812008343/bh2416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008343/bh2416Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008343/bh2416Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives containing either 2-phenyl (Choi et al., 2011a) or 2-(4-fluorophenyl) (Choi et al., 2011b) substituents, 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 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofurn fragment is 38.38 (6)°. The crystal packing is stabilized by weak intermolecular C–H···O hydrogen bonds (Table 1).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011a,b).

Experimental top

77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4 h., 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 443-444 K; R_f = 0.55 (hexane-ethyl acetate, 1:1 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.

Structure description top

For background information and the crystal structures of related compounds, see: Choi et al. (2011a,b).

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 displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

5-Cyclohexyl-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₂₁H₂₁FO₂S	D_x = 1.316 Mg m⁻³
M_r = 356.44	Melting point: 443 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4473 reflections
a = 12.7767 (10) Å	θ = 2.5–28.1°
b = 13.0764 (10) Å	µ = 0.20 mm⁻¹
c = 10.7711 (8) Å	T = 173 K
V = 1799.6 (2) Å³	Block, colourless
Z = 4	0.34 × 0.24 × 0.20 mm
F(000) = 752

Data collection top

Bruker SMART APEXII CCD diffractometer	4503 independent reflections
Radiation source: rotating anode	4036 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.058
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.2°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −17→16
T_min = 0.935, T_max = 0.961	l = −14→14
17893 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0426P)² + 0.2167P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4503 reflections	Δρ_max = 0.33 e Å⁻³
227 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2131 Friedel pairs
0 constraints	Absolute structure parameter: −0.07 (7)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₁H₂₁FO₂S	V = 1799.6 (2) Å³
M_r = 356.44	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.7767 (10) Å	µ = 0.20 mm⁻¹
b = 13.0764 (10) Å	T = 173 K
c = 10.7711 (8) Å	0.34 × 0.24 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4503 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4036 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.961	R_int = 0.058
17893 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.096	Δρ_max = 0.33 e Å⁻³
S = 1.03	Δρ_min = −0.25 e Å⁻³
4503 reflections	Absolute structure: Flack (1983), 2131 Friedel pairs
227 parameters	Absolute structure parameter: −0.07 (7)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.56575 (3)	0.02701 (3)	0.35040 (5)	0.02691 (11)
F1	0.77633 (15)	0.11534 (12)	−0.03264 (18)	0.0792 (6)
O1	0.46206 (10)	0.30803 (10)	0.29361 (13)	0.0277 (3)
O2	0.56405 (11)	−0.00184 (12)	0.48474 (14)	0.0390 (4)
C1	0.49571 (12)	0.14257 (13)	0.33717 (18)	0.0234 (3)
C2	0.40393 (13)	0.17197 (14)	0.40656 (17)	0.0231 (3)
C3	0.33673 (13)	0.12486 (14)	0.49109 (16)	0.0254 (4)
H3	0.3475	0.0555	0.5143	0.031*
C4	0.25446 (14)	0.17975 (15)	0.54083 (17)	0.0257 (4)
C5	0.24014 (14)	0.28249 (15)	0.5060 (2)	0.0296 (4)
H5	0.1833	0.3196	0.5408	0.036*
C6	0.30589 (14)	0.33145 (15)	0.42275 (19)	0.0287 (4)
H6	0.2957	0.4009	0.3997	0.034*
C7	0.38672 (13)	0.27399 (14)	0.37531 (16)	0.0260 (4)
C8	0.52756 (14)	0.22666 (14)	0.27291 (16)	0.0256 (4)
C9	0.17818 (14)	0.12816 (16)	0.62864 (17)	0.0287 (4)
H9	0.2064	0.0585	0.6469	0.034*
C10	0.16664 (19)	0.1834 (2)	0.7521 (2)	0.0443 (5)
H10A	0.1439	0.2547	0.7367	0.053*
H10B	0.2354	0.1858	0.7943	0.053*
C11	0.08727 (19)	0.1306 (2)	0.8365 (2)	0.0554 (7)
H11A	0.1153	0.0634	0.8625	0.067*
H11B	0.0767	0.1725	0.9121	0.067*
C12	−0.01698 (19)	0.1153 (2)	0.7722 (3)	0.0573 (8)
H12A	−0.0642	0.0761	0.8273	0.069*
H12B	−0.0495	0.1827	0.7564	0.069*
C13	−0.00474 (18)	0.0591 (2)	0.6512 (3)	0.0494 (6)
H13A	−0.0736	0.0540	0.6095	0.059*
H13B	0.0206	−0.0112	0.6676	0.059*
C14	0.07219 (16)	0.1139 (2)	0.5661 (2)	0.0405 (5)
H14A	0.0434	0.1816	0.5431	0.049*
H14B	0.0813	0.0737	0.4890	0.049*
C15	0.61838 (13)	0.24653 (16)	0.19341 (17)	0.0269 (4)
C16	0.65392 (17)	0.17134 (18)	0.1135 (2)	0.0389 (5)
H16	0.6172	0.1086	0.1051	0.047*
C17	0.74380 (18)	0.18950 (19)	0.0462 (2)	0.0457 (6)
C18	0.79812 (17)	0.27964 (19)	0.0536 (2)	0.0421 (5)
H18	0.8604	0.2896	0.0069	0.051*
C19	0.76030 (16)	0.35559 (19)	0.1303 (2)	0.0376 (5)
H19	0.7957	0.4194	0.1349	0.045*
C20	0.67083 (14)	0.33938 (16)	0.20081 (19)	0.0306 (4)
H20	0.6455	0.3917	0.2541	0.037*
C21	0.47422 (18)	−0.05631 (16)	0.2771 (2)	0.0378 (5)
H21A	0.5009	−0.1266	0.2794	0.057*
H21B	0.4644	−0.0352	0.1905	0.057*
H21C	0.4071	−0.0530	0.3209	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02477 (19)	0.0252 (2)	0.0307 (2)	0.00363 (16)	0.00124 (19)	0.0016 (2)
F1	0.0930 (12)	0.0564 (10)	0.0883 (13)	0.0007 (9)	0.0641 (10)	−0.0086 (9)
O1	0.0257 (6)	0.0243 (7)	0.0332 (7)	−0.0006 (5)	0.0024 (5)	0.0051 (6)
O2	0.0457 (9)	0.0377 (8)	0.0335 (8)	0.0094 (7)	−0.0076 (7)	0.0065 (7)
C1	0.0219 (7)	0.0237 (8)	0.0246 (9)	−0.0008 (6)	0.0011 (7)	0.0004 (8)
C2	0.0207 (7)	0.0243 (9)	0.0243 (8)	0.0011 (7)	−0.0022 (6)	0.0010 (7)
C3	0.0255 (8)	0.0236 (9)	0.0272 (9)	0.0014 (7)	0.0001 (7)	0.0023 (7)
C4	0.0246 (9)	0.0267 (10)	0.0256 (9)	0.0020 (7)	0.0008 (7)	0.0007 (7)
C5	0.0248 (9)	0.0291 (10)	0.0350 (10)	0.0042 (7)	0.0020 (7)	−0.0021 (8)
C6	0.0279 (9)	0.0232 (9)	0.0352 (10)	0.0026 (7)	−0.0013 (8)	0.0013 (8)
C7	0.0219 (8)	0.0262 (9)	0.0301 (10)	−0.0030 (7)	−0.0022 (7)	0.0023 (7)
C8	0.0244 (8)	0.0264 (10)	0.0260 (9)	0.0005 (7)	−0.0019 (7)	0.0011 (7)
C9	0.0284 (9)	0.0306 (10)	0.0271 (9)	0.0055 (7)	0.0042 (7)	0.0033 (8)
C10	0.0440 (12)	0.0575 (15)	0.0315 (11)	−0.0056 (11)	0.0084 (9)	−0.0057 (10)
C11	0.0643 (15)	0.0647 (17)	0.0373 (13)	−0.0022 (12)	0.0242 (12)	−0.0026 (13)
C12	0.0434 (13)	0.0520 (15)	0.077 (2)	0.0069 (12)	0.0309 (13)	0.0186 (14)
C13	0.0353 (11)	0.0559 (16)	0.0571 (15)	−0.0109 (11)	0.0033 (10)	0.0208 (12)
C14	0.0383 (12)	0.0457 (14)	0.0376 (11)	−0.0115 (10)	−0.0014 (9)	0.0124 (10)
C15	0.0250 (8)	0.0297 (10)	0.0261 (9)	0.0002 (7)	0.0008 (7)	0.0066 (7)
C16	0.0445 (12)	0.0335 (12)	0.0387 (12)	−0.0035 (9)	0.0140 (9)	0.0040 (9)
C17	0.0474 (13)	0.0440 (14)	0.0457 (13)	0.0073 (11)	0.0228 (11)	0.0087 (11)
C18	0.0297 (10)	0.0564 (15)	0.0402 (12)	0.0000 (10)	0.0101 (9)	0.0163 (11)
C19	0.0295 (10)	0.0448 (13)	0.0386 (11)	−0.0125 (9)	−0.0027 (9)	0.0095 (10)
C20	0.0289 (9)	0.0315 (11)	0.0312 (10)	−0.0024 (8)	−0.0044 (8)	0.0049 (8)
C21	0.0447 (12)	0.0281 (10)	0.0406 (12)	−0.0025 (9)	−0.0070 (9)	−0.0039 (9)

Geometric parameters (Å, º) top

S1—O2	1.4954 (15)	C11—C12	1.515 (4)
S1—C1	1.7620 (17)	C11—H11A	0.9900
S1—C21	1.783 (2)	C11—H11B	0.9900
F1—C17	1.355 (3)	C12—C13	1.505 (4)
O1—C8	1.372 (2)	C12—H12A	0.9900
O1—C7	1.378 (2)	C12—H12B	0.9900
C1—C8	1.361 (3)	C13—C14	1.523 (3)
C1—C2	1.443 (2)	C13—H13A	0.9900
C2—C7	1.393 (3)	C13—H13B	0.9900
C2—C3	1.395 (2)	C14—H14A	0.9900
C3—C4	1.381 (2)	C14—H14B	0.9900
C3—H3	0.9500	C15—C16	1.383 (3)
C4—C5	1.407 (3)	C15—C20	1.389 (3)
C4—C9	1.516 (3)	C16—C17	1.378 (3)
C5—C6	1.385 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.370 (3)
C6—C7	1.376 (3)	C18—C19	1.379 (3)
C6—H6	0.9500	C18—H18	0.9500
C8—C15	1.465 (2)	C19—C20	1.389 (3)
C9—C10	1.520 (3)	C19—H19	0.9500
C9—C14	1.524 (3)	C20—H20	0.9500
C9—H9	1.0000	C21—H21A	0.9800
C10—C11	1.527 (3)	C21—H21B	0.9800
C10—H10A	0.9900	C21—H21C	0.9800
C10—H10B	0.9900

O2—S1—C1	106.69 (9)	C10—C11—H11B	109.3
O2—S1—C21	105.37 (10)	H11A—C11—H11B	107.9
C1—S1—C21	98.93 (9)	C13—C12—C11	111.69 (19)
C8—O1—C7	106.23 (14)	C13—C12—H12A	109.3
C8—C1—C2	106.92 (15)	C11—C12—H12A	109.3
C8—C1—S1	125.59 (13)	C13—C12—H12B	109.3
C2—C1—S1	126.83 (13)	C11—C12—H12B	109.3
C7—C2—C3	118.91 (16)	H12A—C12—H12B	107.9
C7—C2—C1	104.97 (15)	C12—C13—C14	111.0 (2)
C3—C2—C1	136.11 (17)	C12—C13—H13A	109.4
C4—C3—C2	119.48 (17)	C14—C13—H13A	109.4
C4—C3—H3	120.3	C12—C13—H13B	109.4
C2—C3—H3	120.3	C14—C13—H13B	109.4
C3—C4—C5	119.46 (17)	H13A—C13—H13B	108.0
C3—C4—C9	120.00 (17)	C13—C14—C9	111.42 (18)
C5—C4—C9	120.51 (16)	C13—C14—H14A	109.3
C6—C5—C4	122.35 (17)	C9—C14—H14A	109.3
C6—C5—H5	118.8	C13—C14—H14B	109.3
C4—C5—H5	118.8	C9—C14—H14B	109.3
C7—C6—C5	116.31 (17)	H14A—C14—H14B	108.0
C7—C6—H6	121.8	C16—C15—C20	119.90 (18)
C5—C6—H6	121.8	C16—C15—C8	119.84 (18)
C6—C7—O1	125.82 (17)	C20—C15—C8	120.22 (18)
C6—C7—C2	123.48 (17)	C17—C16—C15	118.6 (2)
O1—C7—C2	110.69 (15)	C17—C16—H16	120.7
C1—C8—O1	111.19 (15)	C15—C16—H16	120.7
C1—C8—C15	132.60 (17)	F1—C17—C18	119.79 (19)
O1—C8—C15	116.14 (16)	F1—C17—C16	117.5 (2)
C4—C9—C10	113.34 (18)	C18—C17—C16	122.7 (2)
C4—C9—C14	110.48 (16)	C17—C18—C19	118.5 (2)
C10—C9—C14	111.02 (18)	C17—C18—H18	120.8
C4—C9—H9	107.2	C19—C18—H18	120.8
C10—C9—H9	107.2	C18—C19—C20	120.4 (2)
C14—C9—H9	107.2	C18—C19—H19	119.8
C9—C10—C11	111.7 (2)	C20—C19—H19	119.8
C9—C10—H10A	109.3	C19—C20—C15	119.9 (2)
C11—C10—H10A	109.3	C19—C20—H20	120.0
C9—C10—H10B	109.3	C15—C20—H20	120.0
C11—C10—H10B	109.3	S1—C21—H21A	109.5
H10A—C10—H10B	107.9	S1—C21—H21B	109.5
C12—C11—C10	111.8 (2)	H21A—C21—H21B	109.5
C12—C11—H11A	109.3	S1—C21—H21C	109.5
C10—C11—H11A	109.3	H21A—C21—H21C	109.5
C12—C11—H11B	109.3	H21B—C21—H21C	109.5

O2—S1—C1—C8	133.15 (16)	C7—O1—C8—C15	−176.61 (15)
C21—S1—C1—C8	−117.75 (17)	C3—C4—C9—C10	125.5 (2)
O2—S1—C1—C2	−36.29 (18)	C5—C4—C9—C10	−56.7 (2)
C21—S1—C1—C2	72.81 (18)	C3—C4—C9—C14	−109.2 (2)
C8—C1—C2—C7	1.11 (19)	C5—C4—C9—C14	68.6 (2)
S1—C1—C2—C7	172.15 (13)	C4—C9—C10—C11	178.61 (19)
C8—C1—C2—C3	−177.8 (2)	C14—C9—C10—C11	53.6 (3)
S1—C1—C2—C3	−6.8 (3)	C9—C10—C11—C12	−53.3 (3)
C7—C2—C3—C4	0.6 (3)	C10—C11—C12—C13	54.5 (3)
C1—C2—C3—C4	179.4 (2)	C11—C12—C13—C14	−55.9 (3)
C2—C3—C4—C5	−0.4 (3)	C12—C13—C14—C9	56.4 (3)
C2—C3—C4—C9	177.44 (16)	C4—C9—C14—C13	178.2 (2)
C3—C4—C5—C6	0.0 (3)	C10—C9—C14—C13	−55.2 (3)
C9—C4—C5—C6	−177.75 (18)	C1—C8—C15—C16	39.0 (3)
C4—C5—C6—C7	0.0 (3)	O1—C8—C15—C16	−144.42 (19)
C5—C6—C7—O1	−178.59 (17)	C1—C8—C15—C20	−139.0 (2)
C5—C6—C7—C2	0.2 (3)	O1—C8—C15—C20	37.6 (2)
C8—O1—C7—C6	178.97 (17)	C20—C15—C16—C17	2.5 (3)
C8—O1—C7—C2	0.04 (19)	C8—C15—C16—C17	−175.5 (2)
C3—C2—C7—C6	−0.5 (3)	C15—C16—C17—F1	−179.1 (2)
C1—C2—C7—C6	−179.67 (17)	C15—C16—C17—C18	−1.3 (4)
C3—C2—C7—O1	178.43 (15)	F1—C17—C18—C19	176.9 (2)
C1—C2—C7—O1	−0.7 (2)	C16—C17—C18—C19	−0.9 (4)
C2—C1—C8—O1	−1.1 (2)	C17—C18—C19—C20	1.8 (3)
S1—C1—C8—O1	−172.33 (13)	C18—C19—C20—C15	−0.6 (3)
C2—C1—C8—C15	175.59 (19)	C16—C15—C20—C19	−1.6 (3)
S1—C1—C8—C15	4.4 (3)	C8—C15—C20—C19	176.39 (18)
C7—O1—C8—C1	0.71 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···O2ⁱ	0.98	2.30	3.276 (3)	176

Symmetry code: (i) −x+1, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁FO₂S
M_r	356.44
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	12.7767 (10), 13.0764 (10), 10.7711 (8)
V (Å³)	1799.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.34 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.935, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	17893, 4503, 4036
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.096, 1.03
No. of reflections	4503
No. of parameters	227
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25
Absolute structure	Flack (1983), 2131 Friedel pairs
Absolute structure parameter	−0.07 (7)

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

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···O2ⁱ	0.98	2.30	3.276 (3)	175.5

Symmetry code: (i) −x+1, −y, z−1/2.

Acknowledgements

This work was supported by a Dongeui University Foundation grant (2011).

References

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
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Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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