5-Bromo-3-(4-fluoro­phenyl­sulfin­yl)-2-phenyl-1-benzofuran

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

doi:10.1107/S1600536812044054

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3242

doi:10.1107/S1600536812044054

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5-Bromo-3-(4-fluorophenylsulfinyl)-2-phenyl-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 18 October 2012; accepted 24 October 2012; online 31 October 2012)

In the title compound, C₂₀H₁₂BrFO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal, molecules are linked by C—H⋯O and C—H⋯π interactions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 ); Seo et al. (2011 ).

Experimental

Crystal data

C₂₀H₁₂BrFO₂S
M_r = 415.27
Triclinic, $[P \overline 1]$
a = 9.2288 (2) Å
b = 9.4790 (2) Å
c = 10.4939 (2) Å
α = 67.396 (1)°
β = 89.933 (1)°
γ = 82.373 (1)°
V = 838.74 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.60 mm⁻¹
T = 173 K
0.39 × 0.33 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.557, T_max = 0.746
15136 measured reflections
3888 independent reflections
3417 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.079
S = 1.05
3888 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.95	2.41	3.341 (3)	167
C19—H19⋯O1ⁱⁱ	0.95	2.50	3.447 (2)	175
C16—H16⋯Cgⁱⁱⁱ	0.95	2.99	3.832 (2)	148
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y, z-1; (iii) -x, -y+1, -z+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/S1600536812044054/bv2213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044054/bv2213Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812044054/bv2213Isup3.cml

checkCIF report

Comment top

As a part of our ongoing studies of 5-bromo-1-benzofuran derivatives containing 2-phenyl-3-phenylsulfinyl (Choi et al., 2009) and 2-(4-fluorophenyl)-3-phenylsulfinyl (Seo et al., 2011) 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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles formed by the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C9–C14 2-phenyl ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2009); Seo et al. (2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2-phenyl-1-benzofuran (319 mg, 0.8 mmol) in dichloromethane (30 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 63%, m.p. 445-446 K; R_f = 0.75 (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 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. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z + 2; (ii) x, y,z - 1; (iii) - x, - y + 1, - z + 2; (iv) x, y, z + 1.]

5-Bromo-3-(4-fluorophenylsulfinyl)-2-phenyl-1-benzofuran top

Crystal data top

C₂₀H₁₂BrFO₂S	Z = 2
M_r = 415.27	F(000) = 416
Triclinic, P1	D_x = 1.644 Mg m⁻³
Hall symbol: -P 1	Melting point = 446–445 K
a = 9.2288 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4790 (2) Å	Cell parameters from 6293 reflections
c = 10.4939 (2) Å	θ = 2.2–27.5°
α = 67.396 (1)°	µ = 2.60 mm⁻¹
β = 89.933 (1)°	T = 173 K
γ = 82.373 (1)°	Block, colourless
V = 838.74 (3) Å³	0.39 × 0.33 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3888 independent reflections
Radiation source: rotating anode	3417 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.045
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.6°, θ_min = 2.1°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.557, T_max = 0.746	l = −13→13
15136 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)] = 0.030	Hydrogen site location: difference Fourier map
wR(F²) = 0.079	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.032P)² + 0.4488P] where P = (F_o² + 2F_c²)/3
3888 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₂₀H₁₂BrFO₂S	γ = 82.373 (1)°
M_r = 415.27	V = 838.74 (3) Å³
Triclinic, P1	Z = 2
a = 9.2288 (2) Å	Mo Kα radiation
b = 9.4790 (2) Å	µ = 2.60 mm⁻¹
c = 10.4939 (2) Å	T = 173 K
α = 67.396 (1)°	0.39 × 0.33 × 0.22 mm
β = 89.933 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3888 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3417 reflections with I > 2σ(I)
T_min = 0.557, T_max = 0.746	R_int = 0.045
15136 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.05	Δρ_max = 0.65 e Å⁻³
3888 reflections	Δρ_min = −0.74 e Å⁻³
226 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
Br1	0.44656 (2)	1.17299 (2)	0.60200 (2)	0.03743 (9)
S1	0.34716 (5)	0.48730 (6)	0.74923 (5)	0.02461 (11)
F1	−0.06628 (17)	0.76294 (19)	0.26600 (15)	0.0505 (4)
O1	0.25847 (16)	0.62748 (16)	1.05071 (14)	0.0266 (3)
O2	0.49317 (16)	0.5237 (2)	0.69525 (17)	0.0363 (4)
C1	0.2987 (2)	0.5932 (2)	0.8526 (2)	0.0234 (4)
C2	0.3270 (2)	0.7466 (2)	0.8310 (2)	0.0241 (4)
C3	0.3706 (2)	0.8705 (2)	0.7217 (2)	0.0267 (4)
H3	0.3888	0.8656	0.6343	0.032*
C4	0.3862 (2)	1.0009 (2)	0.7466 (2)	0.0282 (4)
C5	0.3610 (2)	1.0122 (3)	0.8731 (2)	0.0321 (5)
H5	0.3731	1.1046	0.8848	0.039*
C6	0.3183 (2)	0.8897 (3)	0.9821 (2)	0.0314 (5)
H6	0.3012	0.8946	1.0697	0.038*
C7	0.3020 (2)	0.7600 (2)	0.9568 (2)	0.0255 (4)
C8	0.2584 (2)	0.5276 (2)	0.9848 (2)	0.0240 (4)
C9	0.2165 (2)	0.3774 (2)	1.0659 (2)	0.0247 (4)
C10	0.2675 (2)	0.2991 (2)	1.2042 (2)	0.0288 (4)
H10	0.3274	0.3452	1.2461	0.035*
C11	0.2304 (3)	0.1551 (3)	1.2792 (2)	0.0367 (5)
H11	0.2672	0.1007	1.3723	0.044*
C12	0.1402 (3)	0.0891 (3)	1.2200 (3)	0.0421 (6)
H12	0.1140	−0.0097	1.2729	0.051*
C13	0.0878 (3)	0.1664 (3)	1.0836 (3)	0.0403 (5)
H13	0.0256	0.1209	1.0432	0.048*
C14	0.1259 (2)	0.3097 (3)	1.0066 (2)	0.0330 (5)
H14	0.0905	0.3624	0.9129	0.040*
C15	0.2184 (2)	0.5861 (2)	0.60419 (19)	0.0227 (4)
C16	0.0772 (2)	0.6487 (3)	0.6157 (2)	0.0299 (4)
H16	0.0468	0.6502	0.7017	0.036*
C17	−0.0195 (2)	0.7090 (3)	0.5006 (2)	0.0351 (5)
H17	−0.1168	0.7531	0.5060	0.042*
C18	0.0288 (2)	0.7034 (3)	0.3788 (2)	0.0328 (5)
C19	0.1680 (3)	0.6428 (3)	0.3644 (2)	0.0320 (5)
H19	0.1977	0.6420	0.2779	0.038*
C20	0.2640 (2)	0.5827 (2)	0.4797 (2)	0.0267 (4)
H20	0.3612	0.5391	0.4735	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04254 (14)	0.02593 (13)	0.04180 (14)	−0.00937 (9)	0.01229 (10)	−0.00950 (10)
S1	0.0270 (2)	0.0261 (3)	0.0238 (2)	−0.00184 (18)	0.00172 (18)	−0.0136 (2)
F1	0.0572 (9)	0.0564 (10)	0.0337 (7)	0.0041 (7)	−0.0179 (7)	−0.0169 (7)
O1	0.0355 (8)	0.0270 (7)	0.0204 (7)	−0.0083 (6)	0.0049 (5)	−0.0113 (6)
O2	0.0255 (7)	0.0541 (10)	0.0394 (9)	−0.0050 (7)	0.0052 (6)	−0.0293 (8)
C1	0.0251 (9)	0.0254 (10)	0.0215 (9)	−0.0040 (7)	0.0017 (7)	−0.0112 (8)
C2	0.0239 (9)	0.0264 (10)	0.0241 (9)	−0.0031 (7)	0.0015 (7)	−0.0123 (8)
C3	0.0288 (10)	0.0271 (10)	0.0246 (10)	−0.0045 (8)	0.0052 (8)	−0.0104 (8)
C4	0.0258 (10)	0.0253 (10)	0.0318 (10)	−0.0049 (8)	0.0037 (8)	−0.0090 (9)
C5	0.0362 (11)	0.0275 (11)	0.0369 (12)	−0.0054 (9)	0.0012 (9)	−0.0170 (10)
C6	0.0402 (12)	0.0327 (12)	0.0274 (10)	−0.0070 (9)	0.0035 (9)	−0.0176 (9)
C7	0.0279 (10)	0.0267 (10)	0.0231 (9)	−0.0060 (8)	0.0034 (7)	−0.0103 (8)
C8	0.0243 (9)	0.0276 (10)	0.0231 (9)	−0.0043 (7)	−0.0002 (7)	−0.0130 (8)
C9	0.0247 (9)	0.0258 (10)	0.0250 (9)	−0.0042 (7)	0.0047 (7)	−0.0112 (8)
C10	0.0281 (10)	0.0293 (11)	0.0279 (10)	−0.0018 (8)	0.0026 (8)	−0.0107 (9)
C11	0.0433 (12)	0.0293 (12)	0.0298 (11)	−0.0002 (9)	0.0084 (9)	−0.0048 (9)
C12	0.0493 (14)	0.0257 (12)	0.0510 (15)	−0.0111 (10)	0.0186 (11)	−0.0126 (11)
C13	0.0401 (13)	0.0371 (13)	0.0515 (15)	−0.0134 (10)	0.0071 (11)	−0.0233 (12)
C14	0.0324 (11)	0.0363 (12)	0.0341 (11)	−0.0072 (9)	0.0014 (9)	−0.0170 (10)
C15	0.0267 (9)	0.0223 (9)	0.0208 (9)	−0.0064 (7)	0.0022 (7)	−0.0093 (8)
C16	0.0285 (10)	0.0374 (12)	0.0265 (10)	−0.0041 (8)	0.0047 (8)	−0.0155 (9)
C17	0.0296 (11)	0.0419 (13)	0.0331 (11)	−0.0004 (9)	−0.0009 (9)	−0.0154 (10)
C18	0.0405 (12)	0.0299 (11)	0.0263 (10)	−0.0058 (9)	−0.0070 (9)	−0.0087 (9)
C19	0.0452 (12)	0.0314 (11)	0.0215 (10)	−0.0089 (9)	0.0060 (9)	−0.0116 (9)
C20	0.0298 (10)	0.0261 (10)	0.0262 (10)	−0.0059 (8)	0.0072 (8)	−0.0118 (9)

Geometric parameters (Å, º) top

Br1—C4	1.900 (2)	C9—C10	1.400 (3)
S1—O2	1.4923 (16)	C10—C11	1.378 (3)
S1—C1	1.7609 (19)	C10—H10	0.9500
S1—C15	1.7941 (19)	C11—C12	1.382 (4)
F1—C18	1.359 (2)	C11—H11	0.9500
O1—C8	1.371 (2)	C12—C13	1.385 (4)
O1—C7	1.375 (2)	C12—H12	0.9500
C1—C8	1.358 (3)	C13—C14	1.380 (3)
C1—C2	1.443 (3)	C13—H13	0.9500
C2—C7	1.390 (3)	C14—H14	0.9500
C2—C3	1.394 (3)	C15—C20	1.383 (3)
C3—C4	1.382 (3)	C15—C16	1.383 (3)
C3—H3	0.9500	C16—C17	1.385 (3)
C4—C5	1.389 (3)	C16—H16	0.9500
C5—C6	1.382 (3)	C17—C18	1.371 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.380 (3)	C18—C19	1.369 (3)
C6—H6	0.9500	C19—C20	1.383 (3)
C8—C9	1.454 (3)	C19—H19	0.9500
C9—C14	1.396 (3)	C20—H20	0.9500

O2—S1—C1	107.36 (9)	C11—C10—H10	120.1
O2—S1—C15	105.38 (9)	C9—C10—H10	120.1
C1—S1—C15	100.79 (9)	C10—C11—C12	120.5 (2)
C8—O1—C7	106.44 (15)	C10—C11—H11	119.8
C8—C1—C2	107.19 (17)	C12—C11—H11	119.8
C8—C1—S1	123.20 (15)	C11—C12—C13	120.2 (2)
C2—C1—S1	127.98 (15)	C11—C12—H12	119.9
C7—C2—C3	119.21 (18)	C13—C12—H12	119.9
C7—C2—C1	104.74 (18)	C14—C13—C12	120.0 (2)
C3—C2—C1	136.05 (18)	C14—C13—H13	120.0
C4—C3—C2	116.90 (19)	C12—C13—H13	120.0
C4—C3—H3	121.6	C13—C14—C9	120.2 (2)
C2—C3—H3	121.6	C13—C14—H14	119.9
C3—C4—C5	123.2 (2)	C9—C14—H14	119.9
C3—C4—Br1	118.81 (16)	C20—C15—C16	120.94 (18)
C5—C4—Br1	118.02 (16)	C20—C15—S1	115.41 (15)
C6—C5—C4	120.30 (19)	C16—C15—S1	123.34 (15)
C6—C5—H5	119.8	C15—C16—C17	119.43 (19)
C4—C5—H5	119.8	C15—C16—H16	120.3
C7—C6—C5	116.44 (19)	C17—C16—H16	120.3
C7—C6—H6	121.8	C18—C17—C16	118.3 (2)
C5—C6—H6	121.8	C18—C17—H17	120.9
O1—C7—C6	125.29 (18)	C16—C17—H17	120.9
O1—C7—C2	110.73 (17)	F1—C18—C19	118.31 (19)
C6—C7—C2	124.0 (2)	F1—C18—C17	118.2 (2)
C1—C8—O1	110.88 (17)	C19—C18—C17	123.52 (19)
C1—C8—C9	133.00 (18)	C18—C19—C20	117.88 (19)
O1—C8—C9	116.11 (17)	C18—C19—H19	121.1
C14—C9—C10	119.4 (2)	C20—C19—H19	121.1
C14—C9—C8	120.44 (19)	C15—C20—C19	119.95 (19)
C10—C9—C8	120.11 (18)	C15—C20—H20	120.0
C11—C10—C9	119.7 (2)	C19—C20—H20	120.0

O2—S1—C1—C8	−127.11 (17)	C7—O1—C8—C9	179.50 (16)
C15—S1—C1—C8	122.87 (17)	C1—C8—C9—C14	−41.0 (3)
O2—S1—C1—C2	36.4 (2)	O1—C8—C9—C14	138.82 (19)
C15—S1—C1—C2	−73.58 (19)	C1—C8—C9—C10	138.7 (2)
C8—C1—C2—C7	0.7 (2)	O1—C8—C9—C10	−41.5 (3)
S1—C1—C2—C7	−164.98 (15)	C14—C9—C10—C11	1.4 (3)
C8—C1—C2—C3	−179.8 (2)	C8—C9—C10—C11	−178.28 (19)
S1—C1—C2—C3	14.5 (3)	C9—C10—C11—C12	−1.7 (3)
C7—C2—C3—C4	−0.1 (3)	C10—C11—C12—C13	0.9 (4)
C1—C2—C3—C4	−179.5 (2)	C11—C12—C13—C14	0.1 (4)
C2—C3—C4—C5	0.2 (3)	C12—C13—C14—C9	−0.4 (3)
C2—C3—C4—Br1	179.60 (14)	C10—C9—C14—C13	−0.4 (3)
C3—C4—C5—C6	0.1 (3)	C8—C9—C14—C13	179.3 (2)
Br1—C4—C5—C6	−179.34 (16)	O2—S1—C15—C20	40.06 (17)
C4—C5—C6—C7	−0.5 (3)	C1—S1—C15—C20	151.62 (15)
C8—O1—C7—C6	−179.2 (2)	O2—S1—C15—C16	−146.37 (18)
C8—O1—C7—C2	1.1 (2)	C1—S1—C15—C16	−34.81 (19)
C5—C6—C7—O1	−179.01 (19)	C20—C15—C16—C17	−0.2 (3)
C5—C6—C7—C2	0.6 (3)	S1—C15—C16—C17	−173.42 (17)
C3—C2—C7—O1	179.31 (17)	C15—C16—C17—C18	0.4 (3)
C1—C2—C7—O1	−1.1 (2)	C16—C17—C18—F1	−179.9 (2)
C3—C2—C7—C6	−0.4 (3)	C16—C17—C18—C19	−0.6 (4)
C1—C2—C7—C6	179.24 (19)	F1—C18—C19—C20	179.91 (19)
C2—C1—C8—O1	0.0 (2)	C17—C18—C19—C20	0.7 (4)
S1—C1—C8—O1	166.47 (13)	C16—C15—C20—C19	0.2 (3)
C2—C1—C8—C9	179.8 (2)	S1—C15—C20—C19	173.95 (16)
S1—C1—C8—C9	−13.7 (3)	C18—C19—C20—C15	−0.4 (3)
C7—O1—C8—C1	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.95	2.41	3.341 (3)	167
C19—H19···O1ⁱⁱ	0.95	2.50	3.447 (2)	175
C16—H16···Cgⁱⁱⁱ	0.95	2.99	3.832 (2)	148

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₂BrFO₂S
M_r	415.27
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.2288 (2), 9.4790 (2), 10.4939 (2)
α, β, γ (°)	67.396 (1), 89.933 (1), 82.373 (1)
V (Å³)	838.74 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.60
Crystal size (mm)	0.39 × 0.33 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.557, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15136, 3888, 3417
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.05
No. of reflections	3888
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.74

Computer programs: APEX2 (Bruker, 2009), SAINT (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
C10—H10···O2ⁱ	0.95	2.41	3.341 (3)	167.1
C19—H19···O1ⁱⁱ	0.95	2.50	3.447 (2)	175.2
C16—H16···Cgⁱⁱⁱ	0.95	2.99	3.832 (2)	148.1

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

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

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
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar