2-(4-Iodo­phen­yl)-5,7-dimethyl-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536808014104

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1088

doi:10.1107/S1600536808014104

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2-(4-Iodophenyl)-5,7-dimethyl-3-methylsulfinyl-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 8 May 2008; accepted 11 May 2008; online 17 May 2008)

The title compound, C₁₇H₁₅IO₂S, was prepared by the oxidation of 2-(4-iodophenyl)-5,7-dimethyl-3-methylsulfanyl-1-benzofuran using 3-chloroperoxybenzoic acid. The 4-iodophenyl ring makes a dihedral angle of 26.0 (1)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of this plane. The crystal structure is stabilized by inter- and intramolecular C—H⋯O hydrogen bonds, and by an I⋯O halogen bond with an I⋯O distance of 3.145 (2) Å and a nearly linear C—I⋯O angle of 164.01 (9)°.

Related literature

For the crystal structures of similar 2-aryl-3-methylsulfinyl-1-benzofuran compounds, see: Choi et al. (2007a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₅IO₂S
M_r = 410.25
Triclinic, $[P \overline 1]$
a = 8.6320 (9) Å
b = 8.917 (1) Å
c = 11.638 (1) Å
α = 94.580 (2)°
β = 100.949 (2)°
γ = 113.725 (2)°
V = 792.90 (14) Å³
Z = 2
Mo Kα radiation
μ = 2.15 mm⁻¹
T = 293 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.594, T_max = 0.647
6882 measured reflections
3408 independent reflections
3214 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.080
S = 1.22
3408 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O1	0.96	2.55	2.975 (4)	107
C16—H16A⋯O2ⁱ	0.96	2.39	3.288 (4)	156
C17—H17B⋯O1ⁱⁱ	0.96	2.51	3.422 (4)	159
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 I, global. DOI: 10.1107/S1600536808014104/zl2115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014104/zl2115Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing studies on the synthesis and structure of 2-aryl-3-methylsulfinyl-1-benzofuran analogues, the crystal structure of 2-(4-bromophenyl)-5-methyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2-(4-bromophenyl)-5,7-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007b) have been described in the literature. Here we report the crystal structure of the title compound, 2-(4-iodophenyl)-5,7-dimethyl-3-methylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.01 Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by three different C—H···O hydrogen bonds; one between a methyl H atom and the furan O atom, i.e. C16—H16B···O1, and a second between a methyl H atom and the oxygen of a neighbouring S═O unit, i.e. C16—H16A···O2ⁱ, and a third between a methyl H atom of the methylsulfinyl substituent and the furan O atom of neighbouring molecules, i.e. C17—H17B···O1ⁱⁱ, (Fig. 2 and Table 1; symmetry code as in Fig. 2). Further stabilization of the structure comes from a weak I···O halogen bond (Fig. 2) (Politzer et al., 2007) between the iodine atom and the oxygen of a neighbouring S═O unit, with an I···O2ⁱⁱⁱ distance of 3.145 (2) Å (Symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar 2-aryl-3-methylsulfinyl-1-benzofuran compounds, see: Choi et al. (2007a,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-chloroperoxybenzoic acid (359 mg, 1.60 mmol) was added in small portions to a stirred solution of 2-(4-iodophenyl)-5,7-dimethyl-3-methylsulfanyl-1-benzofuran (591 mg, 1.50 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 2 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (ethyl acetate) to afford the title compound as a colorless solid [yield 80%, m.p. 450–451 K; R_f = 0.57 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in tetrahydrofuran at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.44 (s, 3H), 2.53 (s, 3H), 3.10 (s, 3H), 7.03 (s, 1H), 7.59 (d, J = 8.44 Hz, 2H), 7.80 (s, 1H), 7.84 (d, J = 8.44 Hz, 2H); EI—MS 410 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. C—H···O hydrogen bond and I···O halogen bond (dotted lines) in the title compound. [Symmetry codes: (i) x, y + 1, z; (ii) -x, -y + 1, -z + 1; (iii) x, y, z - 1; (iv) x, y, z + 1; (v) x, y - 1, z.]

2-(4-Iodophenyl)-5,7-dimethyl-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₇H₁₅IO₂S	Z = 2
M_r = 410.25	F(000) = 404
Triclinic, P1	D_x = 1.718 Mg m⁻³
Hall symbol: -p_1	Melting point = 450–451 K
a = 8.6320 (9) Å	Mo Kα radiation, λ = 0.71069 Å
b = 8.917 (1) Å	Cell parameters from 5631 reflections
c = 11.638 (1) Å	θ = 2.5–28.3°
α = 94.580 (2)°	µ = 2.15 mm⁻¹
β = 100.949 (2)°	T = 293 K
γ = 113.725 (2)°	Block, colorless
V = 792.90 (14) Å³	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3408 independent reflections
Radiation source: fine-focus sealed tube	3214 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.8°
ϕ and ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −11→11
T_min = 0.594, T_max = 0.647	l = −14→14
6882 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + (0.0374P)² + 0.4132P] where P = (F_o² + 2F_c²)/3
3408 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₁₇H₁₅IO₂S	γ = 113.725 (2)°
M_r = 410.25	V = 792.90 (14) Å³
Triclinic, P1	Z = 2
a = 8.6320 (9) Å	Mo Kα radiation
b = 8.917 (1) Å	µ = 2.15 mm⁻¹
c = 11.638 (1) Å	T = 293 K
α = 94.580 (2)°	0.40 × 0.20 × 0.20 mm
β = 100.949 (2)°

Data collection top

Bruker SMART CCD diffractometer	3408 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	3214 reflections with I > 2σ(I)
T_min = 0.594, T_max = 0.647	R_int = 0.029
6882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.22	Δρ_max = 0.50 e Å⁻³
3408 reflections	Δρ_min = −0.66 e Å⁻³
192 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
I	0.26443 (2)	0.23987 (2)	−0.006964 (16)	0.03233 (9)
S	0.10120 (10)	0.19886 (8)	0.60394 (7)	0.02931 (16)
O1	0.3173 (3)	0.6586 (2)	0.54519 (18)	0.0262 (4)
O2	0.2055 (3)	0.1813 (3)	0.7150 (2)	0.0374 (5)
C1	0.1717 (4)	0.4134 (3)	0.6002 (3)	0.0262 (6)
C2	0.2089 (4)	0.5443 (3)	0.6979 (3)	0.0259 (5)
C3	0.1802 (4)	0.5533 (4)	0.8114 (3)	0.0294 (6)
H3	0.1197	0.4569	0.8393	0.035*
C4	0.2430 (4)	0.7078 (4)	0.8822 (3)	0.0309 (6)
C5	0.3335 (4)	0.8521 (4)	0.8378 (3)	0.0307 (6)
H5	0.3738	0.9548	0.8862	0.037*
C6	0.3655 (4)	0.8489 (4)	0.7256 (3)	0.0282 (6)
C7	0.2995 (4)	0.6914 (3)	0.6586 (3)	0.0256 (6)
C8	0.2386 (4)	0.4876 (3)	0.5117 (3)	0.0256 (5)
C9	0.2460 (4)	0.4269 (3)	0.3936 (2)	0.0247 (5)
C10	0.1189 (4)	0.2744 (4)	0.3281 (3)	0.0286 (6)
H10	0.0280	0.2098	0.3599	0.034*
C11	0.1279 (4)	0.2191 (4)	0.2158 (3)	0.0292 (6)
H11	0.0438	0.1169	0.1728	0.035*
C12	0.2623 (4)	0.3162 (4)	0.1674 (3)	0.0268 (6)
C13	0.3902 (4)	0.4699 (4)	0.2319 (3)	0.0289 (6)
H13	0.4803	0.5348	0.1997	0.035*
C14	0.3811 (4)	0.5239 (3)	0.3437 (3)	0.0274 (6)
H14	0.4656	0.6259	0.3866	0.033*
C15	0.2162 (5)	0.7226 (5)	1.0062 (3)	0.0416 (8)
H15A	0.0937	0.6706	1.0029	0.062*
H15B	0.2633	0.8380	1.0409	0.062*
H15C	0.2745	0.6687	1.0538	0.062*
C16	0.4651 (4)	1.0036 (4)	0.6797 (3)	0.0387 (7)
H16A	0.3979	1.0671	0.6682	0.058*
H16B	0.4867	0.9730	0.6054	0.058*
H16C	0.5742	1.0693	0.7362	0.058*
C17	−0.1093 (4)	0.1531 (4)	0.6283 (4)	0.0471 (9)
H17A	−0.1675	0.0368	0.6314	0.071*
H17B	−0.1764	0.1801	0.5646	0.071*
H17C	−0.0976	0.2176	0.7022	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.03823 (13)	0.03425 (13)	0.02494 (12)	0.01616 (9)	0.00863 (8)	0.00135 (8)
S	0.0364 (4)	0.0219 (3)	0.0299 (4)	0.0120 (3)	0.0091 (3)	0.0058 (3)
O1	0.0313 (10)	0.0209 (9)	0.0256 (10)	0.0103 (8)	0.0077 (8)	0.0028 (8)
O2	0.0405 (12)	0.0360 (12)	0.0384 (13)	0.0193 (10)	0.0058 (10)	0.0135 (10)
C1	0.0298 (13)	0.0227 (13)	0.0263 (14)	0.0123 (11)	0.0052 (11)	0.0037 (11)
C2	0.0287 (13)	0.0234 (13)	0.0264 (14)	0.0126 (11)	0.0052 (11)	0.0045 (11)
C3	0.0312 (14)	0.0304 (14)	0.0289 (15)	0.0145 (12)	0.0085 (12)	0.0075 (12)
C4	0.0295 (14)	0.0385 (16)	0.0265 (15)	0.0166 (13)	0.0069 (11)	0.0027 (12)
C5	0.0298 (14)	0.0269 (14)	0.0318 (15)	0.0109 (12)	0.0050 (12)	−0.0023 (12)
C6	0.0240 (13)	0.0253 (13)	0.0339 (15)	0.0100 (11)	0.0068 (11)	0.0011 (11)
C7	0.0254 (13)	0.0250 (13)	0.0264 (14)	0.0117 (11)	0.0049 (11)	0.0031 (11)
C8	0.0260 (13)	0.0219 (13)	0.0269 (14)	0.0097 (10)	0.0032 (11)	0.0036 (11)
C9	0.0271 (13)	0.0237 (13)	0.0224 (13)	0.0114 (11)	0.0031 (10)	0.0042 (10)
C10	0.0275 (13)	0.0271 (14)	0.0272 (14)	0.0077 (11)	0.0060 (11)	0.0051 (11)
C11	0.0294 (14)	0.0248 (13)	0.0257 (14)	0.0067 (11)	0.0017 (11)	0.0000 (11)
C12	0.0299 (14)	0.0283 (14)	0.0233 (13)	0.0150 (11)	0.0038 (11)	0.0031 (11)
C13	0.0293 (14)	0.0277 (14)	0.0296 (15)	0.0109 (11)	0.0091 (12)	0.0069 (11)
C14	0.0276 (13)	0.0227 (13)	0.0271 (14)	0.0078 (11)	0.0037 (11)	0.0017 (11)
C15	0.0498 (19)	0.0454 (18)	0.0279 (17)	0.0184 (15)	0.0118 (15)	0.0014 (14)
C16	0.0398 (17)	0.0259 (15)	0.0469 (19)	0.0079 (13)	0.0182 (15)	0.0024 (14)
C17	0.0318 (16)	0.0336 (17)	0.076 (3)	0.0111 (14)	0.0151 (17)	0.0201 (18)

Geometric parameters (Å, º) top

I—C12	2.094 (3)	C9—C10	1.396 (4)
I—O2ⁱ	3.145 (2)	C9—C14	1.404 (4)
S—O2	1.486 (2)	C10—C11	1.387 (4)
S—C1	1.766 (3)	C10—H10	0.9300
S—C17	1.780 (4)	C11—C12	1.390 (4)
O1—C7	1.379 (3)	C11—H11	0.9300
O1—C8	1.382 (3)	C12—C13	1.401 (4)
C1—C8	1.364 (4)	C13—C14	1.378 (4)
C1—C2	1.452 (4)	C13—H13	0.9300
C2—C3	1.391 (4)	C14—H14	0.9300
C2—C7	1.396 (4)	C15—H15A	0.9600
C3—C4	1.385 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.409 (4)	C16—H16A	0.9600
C4—C15	1.508 (4)	C16—H16B	0.9600
C5—C6	1.385 (4)	C16—H16C	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.385 (4)	C17—H17B	0.9600
C6—C16	1.505 (4)	C17—H17C	0.9600
C8—C9	1.459 (4)

C12—I—O2ⁱ	164.01 (9)	C11—C10—H10	119.9
O2—S—C1	107.81 (13)	C9—C10—H10	119.9
O2—S—C17	105.98 (17)	C10—C11—C12	120.1 (3)
C1—S—C17	99.04 (15)	C10—C11—H11	119.9
C7—O1—C8	106.5 (2)	C12—C11—H11	119.9
C8—C1—C2	107.5 (2)	C11—C12—C13	120.3 (3)
C8—C1—S	123.8 (2)	C11—C12—I	119.8 (2)
C2—C1—S	127.1 (2)	C13—C12—I	119.8 (2)
C3—C2—C7	119.0 (3)	C14—C13—C12	119.4 (3)
C3—C2—C1	136.5 (3)	C14—C13—H13	120.3
C7—C2—C1	104.5 (2)	C12—C13—H13	120.3
C4—C3—C2	119.1 (3)	C13—C14—C9	120.9 (3)
C4—C3—H3	120.5	C13—C14—H14	119.5
C2—C3—H3	120.5	C9—C14—H14	119.5
C3—C4—C5	119.4 (3)	C4—C15—H15A	109.5
C3—C4—C15	120.7 (3)	C4—C15—H15B	109.5
C5—C4—C15	119.9 (3)	H15A—C15—H15B	109.5
C6—C5—C4	123.4 (3)	C4—C15—H15C	109.5
C6—C5—H5	118.3	H15A—C15—H15C	109.5
C4—C5—H5	118.3	H15B—C15—H15C	109.5
C7—C6—C5	114.7 (3)	C6—C16—H16A	109.5
C7—C6—C16	122.2 (3)	C6—C16—H16B	109.5
C5—C6—C16	123.0 (3)	H16A—C16—H16B	109.5
O1—C7—C6	124.7 (3)	C6—C16—H16C	109.5
O1—C7—C2	110.9 (2)	H16A—C16—H16C	109.5
C6—C7—C2	124.4 (3)	H16B—C16—H16C	109.5
C1—C8—O1	110.5 (2)	S—C17—H17A	109.5
C1—C8—C9	134.5 (3)	S—C17—H17B	109.5
O1—C8—C9	115.0 (2)	H17A—C17—H17B	109.5
C10—C9—C14	119.2 (3)	S—C17—H17C	109.5
C10—C9—C8	121.0 (3)	H17A—C17—H17C	109.5
C14—C9—C8	119.8 (2)	H17B—C17—H17C	109.5
C11—C10—C9	120.1 (3)

O2—S—C1—C8	120.8 (3)	C1—C2—C7—O1	0.7 (3)
C17—S—C1—C8	−129.1 (3)	C3—C2—C7—C6	0.5 (4)
O2—S—C1—C2	−43.3 (3)	C1—C2—C7—C6	−178.1 (3)
C17—S—C1—C2	66.8 (3)	C2—C1—C8—O1	0.1 (3)
C8—C1—C2—C3	−178.7 (3)	S—C1—C8—O1	−166.67 (19)
S—C1—C2—C3	−12.5 (5)	C2—C1—C8—C9	179.4 (3)
C8—C1—C2—C7	−0.5 (3)	S—C1—C8—C9	12.6 (5)
S—C1—C2—C7	165.7 (2)	C7—O1—C8—C1	0.4 (3)
C7—C2—C3—C4	−0.3 (4)	C7—O1—C8—C9	−179.1 (2)
C1—C2—C3—C4	177.8 (3)	C1—C8—C9—C10	27.6 (5)
C2—C3—C4—C5	0.3 (4)	O1—C8—C9—C10	−153.1 (3)
C2—C3—C4—C15	−179.4 (3)	C1—C8—C9—C14	−153.4 (3)
C3—C4—C5—C6	−0.6 (5)	O1—C8—C9—C14	25.9 (4)
C15—C4—C5—C6	179.1 (3)	C14—C9—C10—C11	0.8 (4)
C4—C5—C6—C7	0.7 (4)	C8—C9—C10—C11	179.8 (3)
C4—C5—C6—C16	−178.9 (3)	C9—C10—C11—C12	−0.8 (4)
C8—O1—C7—C6	178.1 (3)	C10—C11—C12—C13	0.4 (4)
C8—O1—C7—C2	−0.7 (3)	C10—C11—C12—I	−175.5 (2)
C5—C6—C7—O1	−179.4 (3)	C11—C12—C13—C14	−0.1 (4)
C16—C6—C7—O1	0.2 (5)	I—C12—C13—C14	175.8 (2)
C5—C6—C7—C2	−0.7 (4)	C12—C13—C14—C9	0.2 (4)
C16—C6—C7—C2	178.9 (3)	C10—C9—C14—C13	−0.5 (4)
C3—C2—C7—O1	179.3 (2)	C8—C9—C14—C13	−179.5 (3)

Symmetry code: (i) x, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1	0.96	2.55	2.975 (4)	107
C16—H16A···O2ⁱⁱ	0.96	2.39	3.288 (4)	156
C17—H17B···O1ⁱⁱⁱ	0.96	2.51	3.422 (4)	159

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅IO₂S
M_r	410.25
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.6320 (9), 8.917 (1), 11.638 (1)
α, β, γ (°)	94.580 (2), 100.949 (2), 113.725 (2)
V (Å³)	792.90 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.594, 0.647
No. of measured, independent and observed [I > 2σ(I)] reflections	6882, 3408, 3214
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.080, 1.22
No. of reflections	3408
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.66

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C16—H16B···O1	0.96	2.55	2.975 (4)	107.2
C16—H16A···O2ⁱ	0.96	2.39	3.288 (4)	155.5
C17—H17B···O1ⁱⁱ	0.96	2.51	3.422 (4)	159.1

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

Acknowledgements

This work was supported by a grant from Dongeui University (2008 A A098).

References

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