2-(4-Fluoro­phen­yl)-5-iodo-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536812013086

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1237

doi:10.1107/S1600536812013086

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2-(4-Fluorophenyl)-5-iodo-3-phenylsulfinyl-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 19 March 2012; accepted 26 March 2012; online 27 March 2012)

In the title compound, C₂₀H₁₂FIO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.014 (1) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 8.0 (1) and 86.06 (6)°, respectively. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds. The crystal structure also exhibits weak π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.547 (2) Å, interplanar distance = 3.397 (2) Å and slippage = 1.021 (2) Å].

Related literature

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

Experimental

Crystal data

C₂₀H₁₂FIO₂S
M_r = 462.26
Triclinic, $[P \overline 1]$
a = 8.1771 (2) Å
b = 9.8877 (2) Å
c = 11.8423 (3) Å
α = 103.108 (1)°
β = 90.872 (1)°
γ = 111.546 (1)°
V = 862.23 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.00 mm⁻¹
T = 173 K
0.27 × 0.26 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.516, T_max = 0.746
15186 measured reflections
3974 independent reflections
3696 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.060
S = 1.07
3974 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2ⁱ	0.95	2.38	3.297 (3)	163
Symmetry code: (i) 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/S1600536812013086/kj2197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013086/kj2197Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013086/kj2197Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2-(4-fluorophenyl)-5-halo-3-phenylsulfinyl-1-benzofuran derivatives containing 5-chloro (Choi et al., 2011) and 5-bromo (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 0.014 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 8.0 (1)° and 86.06 (6)°, respectively. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is further stabilized by weak π–π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱ distance of 3.547 (2) Å and an interplanar distance of 3.397 (2) Å resulting in a slippage of 1.021 (2) Å (Cg1 and Cg2are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively).

Related literature top

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

Experimental top

77% 3-Chloroperoxybenzoic acid (179 mg, 0.8 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-phenylsulfanyl-1-benzofuran (312 mg, 0.7 mmol) in dichloromethane (30 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 52%, m.p. 435–436 K; R_f = 0.49 (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.

Structure description top

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

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.
	Fig. 2. A view of the C—H···O and π–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, z; (ii) - x, - y + 1, -z + 1; (iii) - x, - y + 1, - z + 1.]

2-(4-Fluorophenyl)-5-iodo-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₀H₁₂FIO₂S	Z = 2
M_r = 462.26	F(000) = 452
Triclinic, P1	D_x = 1.780 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1771 (2) Å	Cell parameters from 9967 reflections
b = 9.8877 (2) Å	θ = 2.5–27.5°
c = 11.8423 (3) Å	µ = 2.00 mm⁻¹
α = 103.108 (1)°	T = 173 K
β = 90.872 (1)°	Block, colourless
γ = 111.546 (1)°	0.27 × 0.26 × 0.12 mm
V = 862.23 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3974 independent reflections
Radiation source: rotating anode	3696 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.026
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.516, T_max = 0.746	l = −15→15
15186 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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F²) = 0.060	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0266P)² + 0.5718P] where P = (F_o² + 2F_c²)/3
3974 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

C₂₀H₁₂FIO₂S	γ = 111.546 (1)°
M_r = 462.26	V = 862.23 (4) Å³
Triclinic, P1	Z = 2
a = 8.1771 (2) Å	Mo Kα radiation
b = 9.8877 (2) Å	µ = 2.00 mm⁻¹
c = 11.8423 (3) Å	T = 173 K
α = 103.108 (1)°	0.27 × 0.26 × 0.12 mm
β = 90.872 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3974 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3696 reflections with I > 2σ(I)
T_min = 0.516, T_max = 0.746	R_int = 0.026
15186 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 1.07	Δρ_max = 0.50 e Å⁻³
3974 reflections	Δρ_min = −0.75 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
I1	0.02004 (2)	0.736536 (19)	0.939462 (12)	0.04406 (7)
S1	0.04558 (6)	0.18031 (5)	0.55834 (4)	0.02240 (10)
F1	0.4764 (2)	0.12714 (16)	0.06431 (11)	0.0421 (3)
O1	0.29632 (18)	0.56238 (13)	0.46924 (11)	0.0224 (3)
O2	−0.10716 (18)	0.17443 (17)	0.62692 (14)	0.0317 (3)
C1	0.1437 (2)	0.36524 (19)	0.54025 (15)	0.0203 (3)
C2	0.1408 (2)	0.4983 (2)	0.61933 (15)	0.0212 (3)
C3	0.0716 (3)	0.5302 (2)	0.72497 (16)	0.0252 (4)
H3	0.0036	0.4528	0.7598	0.030*
C4	0.1067 (3)	0.6796 (2)	0.77636 (17)	0.0283 (4)
C5	0.2028 (3)	0.7961 (2)	0.72598 (18)	0.0296 (4)
H5	0.2227	0.8971	0.7644	0.035*
C6	0.2688 (3)	0.7648 (2)	0.62058 (17)	0.0267 (4)
H6	0.3329	0.8419	0.5843	0.032*
C7	0.2368 (2)	0.6155 (2)	0.57083 (15)	0.0217 (3)
C8	0.2380 (2)	0.40854 (19)	0.45144 (15)	0.0203 (3)
C9	0.2959 (2)	0.3331 (2)	0.34844 (15)	0.0212 (3)
C10	0.2368 (3)	0.1764 (2)	0.31272 (17)	0.0278 (4)
H10	0.1543	0.1169	0.3549	0.033*
C11	0.2971 (3)	0.1071 (2)	0.21679 (18)	0.0317 (4)
H11	0.2572	0.0007	0.1929	0.038*
C12	0.4154 (3)	0.1950 (2)	0.15691 (16)	0.0289 (4)
C13	0.4753 (3)	0.3489 (2)	0.18758 (17)	0.0283 (4)
H13	0.5565	0.4068	0.1439	0.034*
C14	0.4147 (3)	0.4179 (2)	0.28375 (16)	0.0248 (4)
H14	0.4545	0.5244	0.3059	0.030*
C15	0.2209 (2)	0.1910 (2)	0.65768 (16)	0.0226 (4)
C16	0.2111 (3)	0.2277 (3)	0.77601 (18)	0.0346 (5)
H16	0.1115	0.2458	0.8053	0.042*
C17	0.3483 (4)	0.2380 (3)	0.8519 (2)	0.0433 (6)
H17	0.3428	0.2630	0.9337	0.052*
C18	0.4935 (3)	0.2120 (3)	0.8089 (2)	0.0386 (5)
H18	0.5883	0.2211	0.8613	0.046*
C19	0.5009 (3)	0.1729 (2)	0.6898 (2)	0.0330 (4)
H19	0.6001	0.1541	0.6605	0.040*
C20	0.3635 (3)	0.1612 (2)	0.61308 (18)	0.0275 (4)
H20	0.3670	0.1331	0.5312	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.04049 (10)	0.06314 (12)	0.02678 (8)	0.02727 (8)	0.00553 (6)	−0.00508 (7)
S1	0.0202 (2)	0.0189 (2)	0.0272 (2)	0.00549 (17)	0.00357 (17)	0.00708 (16)
F1	0.0526 (9)	0.0506 (8)	0.0284 (6)	0.0319 (7)	0.0107 (6)	−0.0008 (6)
O1	0.0269 (7)	0.0166 (6)	0.0225 (6)	0.0077 (5)	0.0037 (5)	0.0036 (5)
O2	0.0197 (7)	0.0361 (8)	0.0429 (8)	0.0101 (6)	0.0104 (6)	0.0171 (6)
C1	0.0192 (8)	0.0192 (8)	0.0230 (8)	0.0079 (7)	0.0014 (7)	0.0050 (6)
C2	0.0194 (9)	0.0219 (8)	0.0220 (8)	0.0090 (7)	−0.0003 (7)	0.0030 (7)
C3	0.0221 (9)	0.0305 (10)	0.0235 (9)	0.0116 (8)	0.0023 (7)	0.0046 (7)
C4	0.0250 (10)	0.0359 (10)	0.0230 (9)	0.0159 (9)	−0.0008 (7)	−0.0020 (7)
C5	0.0302 (11)	0.0250 (9)	0.0311 (10)	0.0141 (8)	−0.0030 (8)	−0.0033 (7)
C6	0.0281 (10)	0.0208 (9)	0.0300 (9)	0.0099 (8)	0.0000 (8)	0.0032 (7)
C7	0.0218 (9)	0.0223 (8)	0.0213 (8)	0.0101 (7)	0.0009 (7)	0.0029 (7)
C8	0.0201 (9)	0.0167 (8)	0.0232 (8)	0.0068 (7)	−0.0004 (7)	0.0038 (6)
C9	0.0216 (9)	0.0226 (8)	0.0194 (8)	0.0097 (7)	0.0006 (7)	0.0035 (7)
C10	0.0340 (11)	0.0228 (9)	0.0260 (9)	0.0106 (8)	0.0054 (8)	0.0049 (7)
C11	0.0414 (12)	0.0258 (9)	0.0281 (10)	0.0166 (9)	0.0011 (9)	0.0008 (8)
C12	0.0311 (11)	0.0391 (11)	0.0200 (8)	0.0217 (9)	0.0011 (8)	−0.0001 (8)
C13	0.0260 (10)	0.0367 (10)	0.0231 (9)	0.0131 (9)	0.0042 (7)	0.0069 (8)
C14	0.0245 (9)	0.0236 (9)	0.0247 (9)	0.0082 (8)	0.0019 (7)	0.0044 (7)
C15	0.0209 (9)	0.0199 (8)	0.0281 (9)	0.0074 (7)	0.0039 (7)	0.0089 (7)
C16	0.0363 (12)	0.0484 (13)	0.0304 (10)	0.0265 (11)	0.0095 (9)	0.0134 (9)
C17	0.0509 (15)	0.0615 (15)	0.0276 (10)	0.0328 (13)	0.0023 (10)	0.0115 (10)
C18	0.0343 (12)	0.0424 (12)	0.0439 (13)	0.0185 (10)	−0.0033 (10)	0.0139 (10)
C19	0.0247 (10)	0.0329 (11)	0.0477 (12)	0.0148 (9)	0.0083 (9)	0.0157 (9)
C20	0.0280 (10)	0.0255 (9)	0.0328 (10)	0.0125 (8)	0.0089 (8)	0.0103 (8)

Geometric parameters (Å, º) top

I1—C4	2.096 (2)	C9—C10	1.399 (3)
S1—O2	1.4905 (15)	C10—C11	1.384 (3)
S1—C1	1.7716 (18)	C10—H10	0.9500
S1—C15	1.7978 (19)	C11—C12	1.371 (3)
F1—C12	1.353 (2)	C11—H11	0.9500
O1—C7	1.371 (2)	C12—C13	1.372 (3)
O1—C8	1.380 (2)	C13—C14	1.386 (3)
C1—C8	1.368 (3)	C13—H13	0.9500
C1—C2	1.440 (2)	C14—H14	0.9500
C2—C7	1.392 (3)	C15—C16	1.377 (3)
C2—C3	1.400 (3)	C15—C20	1.388 (3)
C3—C4	1.382 (3)	C16—C17	1.386 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.401 (3)	C17—C18	1.385 (4)
C5—C6	1.383 (3)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.384 (3)
C6—C7	1.383 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.388 (3)
C8—C9	1.460 (2)	C19—H19	0.9500
C9—C14	1.397 (3)	C20—H20	0.9500

O2—S1—C1	107.18 (8)	C11—C10—H10	119.6
O2—S1—C15	106.52 (9)	C9—C10—H10	119.6
C1—S1—C15	97.14 (8)	C12—C11—C10	118.61 (19)
C7—O1—C8	106.99 (14)	C12—C11—H11	120.7
C8—C1—C2	107.66 (15)	C10—C11—H11	120.7
C8—C1—S1	126.91 (14)	F1—C12—C11	118.54 (19)
C2—C1—S1	125.42 (14)	F1—C12—C13	118.78 (19)
C7—C2—C3	119.34 (17)	C11—C12—C13	122.67 (18)
C7—C2—C1	104.82 (15)	C12—C13—C14	118.54 (19)
C3—C2—C1	135.82 (17)	C12—C13—H13	120.7
C4—C3—C2	116.96 (18)	C14—C13—H13	120.7
C4—C3—H3	121.5	C13—C14—C9	120.84 (18)
C2—C3—H3	121.5	C13—C14—H14	119.6
C3—C4—C5	122.95 (18)	C9—C14—H14	119.6
C3—C4—I1	118.98 (15)	C16—C15—C20	121.34 (18)
C5—C4—I1	118.05 (14)	C16—C15—S1	119.61 (15)
C6—C5—C4	120.26 (18)	C20—C15—S1	119.05 (15)
C6—C5—H5	119.9	C15—C16—C17	119.1 (2)
C4—C5—H5	119.9	C15—C16—H16	120.4
C7—C6—C5	116.56 (18)	C17—C16—H16	120.4
C7—C6—H6	121.7	C18—C17—C16	120.3 (2)
C5—C6—H6	121.7	C18—C17—H17	119.9
O1—C7—C6	125.34 (17)	C16—C17—H17	119.9
O1—C7—C2	110.74 (15)	C19—C18—C17	120.2 (2)
C6—C7—C2	123.92 (17)	C19—C18—H18	119.9
C1—C8—O1	109.79 (15)	C17—C18—H18	119.9
C1—C8—C9	135.62 (16)	C18—C19—C20	120.0 (2)
O1—C8—C9	114.52 (15)	C18—C19—H19	120.0
C14—C9—C10	118.46 (17)	C20—C19—H19	120.0
C14—C9—C8	119.83 (16)	C19—C20—C15	119.06 (19)
C10—C9—C8	121.71 (17)	C19—C20—H20	120.5
C11—C10—C9	120.86 (19)	C15—C20—H20	120.5

O2—S1—C1—C8	−153.19 (16)	C7—O1—C8—C9	−177.64 (15)
C15—S1—C1—C8	97.02 (18)	C1—C8—C9—C14	−170.7 (2)
O2—S1—C1—C2	28.24 (18)	O1—C8—C9—C14	5.9 (2)
C15—S1—C1—C2	−81.55 (17)	C1—C8—C9—C10	8.5 (3)
C8—C1—C2—C7	−0.1 (2)	O1—C8—C9—C10	−174.81 (17)
S1—C1—C2—C7	178.71 (13)	C14—C9—C10—C11	1.2 (3)
C8—C1—C2—C3	−178.5 (2)	C8—C9—C10—C11	−178.14 (18)
S1—C1—C2—C3	0.3 (3)	C9—C10—C11—C12	−0.3 (3)
C7—C2—C3—C4	−1.2 (3)	C10—C11—C12—F1	178.92 (18)
C1—C2—C3—C4	177.1 (2)	C10—C11—C12—C13	−0.6 (3)
C2—C3—C4—C5	1.6 (3)	F1—C12—C13—C14	−178.90 (18)
C2—C3—C4—I1	−176.41 (13)	C11—C12—C13—C14	0.6 (3)
C3—C4—C5—C6	−0.5 (3)	C12—C13—C14—C9	0.3 (3)
I1—C4—C5—C6	177.47 (15)	C10—C9—C14—C13	−1.1 (3)
C4—C5—C6—C7	−0.9 (3)	C8—C9—C14—C13	178.18 (17)
C8—O1—C7—C6	179.10 (18)	O2—S1—C15—C16	−15.33 (19)
C8—O1—C7—C2	0.1 (2)	C1—S1—C15—C16	95.01 (17)
C5—C6—C7—O1	−177.58 (18)	O2—S1—C15—C20	164.42 (15)
C5—C6—C7—C2	1.3 (3)	C1—S1—C15—C20	−85.24 (16)
C3—C2—C7—O1	178.77 (16)	C20—C15—C16—C17	1.3 (3)
C1—C2—C7—O1	0.0 (2)	S1—C15—C16—C17	−178.96 (18)
C3—C2—C7—C6	−0.3 (3)	C15—C16—C17—C18	0.2 (4)
C1—C2—C7—C6	−179.03 (18)	C16—C17—C18—C19	−1.2 (4)
C2—C1—C8—O1	0.1 (2)	C17—C18—C19—C20	0.7 (3)
S1—C1—C8—O1	−178.64 (13)	C18—C19—C20—C15	0.8 (3)
C2—C1—C8—C9	176.9 (2)	C16—C15—C20—C19	−1.8 (3)
S1—C1—C8—C9	−1.9 (3)	S1—C15—C20—C19	178.46 (15)
C7—O1—C8—C1	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ⁱ	0.95	2.38	3.297 (3)	163

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₂FIO₂S
M_r	462.26
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.1771 (2), 9.8877 (2), 11.8423 (3)
α, β, γ (°)	103.108 (1), 90.872 (1), 111.546 (1)
V (Å³)	862.23 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.00
Crystal size (mm)	0.27 × 0.26 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.516, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15186, 3974, 3696
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.060, 1.07
No. of reflections	3974
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.75

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
C19—H19···O2ⁱ	0.95	2.38	3.297 (3)	163.4

Symmetry code: (i) x+1, y, z.

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. (2011). Acta Cryst. E67, o498. 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

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Volume 68| Part 4| April 2012| Page o1237

doi:10.1107/S1600536812013086

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