Propyl 2-(5-chloro-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

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

doi:10.1107/S1600536809004735

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o521

doi:10.1107/S1600536809004735

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Propyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate

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 9 February 2009; accepted 10 February 2009; online 13 February 2009)

In the title compound, C₁₄H₁₅ClO₄S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π–π interactions between the benzene rings of neighbouring molecules [centroid-to-centroid distance = 3.635 (3) Å], and by C—H⋯π interactions between a propyl methylene H atom and the furan ring of an adjacent molecule. In addition, the crystal structure exhibits weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetates, see: Choi et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₄H₁₅ClO₄S
M_r = 314.77
Triclinic, $[P \overline 1]$
a = 8.528 (2) Å
b = 9.585 (3) Å
c = 10.195 (3) Å
α = 73.452 (4)°
β = 81.773 (5)°
γ = 65.747 (4)°
V = 728.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.842, T_max = 0.961
5062 measured reflections
2468 independent reflections
2304 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.094
S = 1.07
2468 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Cg2ⁱ	0.99	2.74	3.666 (3)	155
C3—H3⋯O4ⁱⁱ	0.95	2.44	3.353 (2)	160
C5—H5⋯O3ⁱⁱⁱ	0.95	2.50	3.373 (2)	152
C9—H9A⋯O4^iv	0.99	2.35	3.321 (2)	166
C9—H9B⋯O1^v	0.99	2.54	3.489 (2)	161
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+1; (iii) -x, -y+1, -z+2; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y+1, -z+2. Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring

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 global, I. DOI: 10.1107/S1600536809004735/gk2190sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004735/gk2190Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing research on the synthesis and structure of alkyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, we have described the crystal structures of ethyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2007) and methyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008). Here we report the crystal structure of the title compound, propyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Fig. 1). Regardless of the lengths of the alkyl substituent arrangement of the molecules in the three crystal structures is very similar. The benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π—π interactions between the benzene rings of neighbouring molecules. The Cg1···Cg1ⁱⁱ distance is 3.635 (3) Å (Cg1 is the centroid of the C2–C7 benzene ring; symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions between the hydrogen of 12-methylene group and the furan ring of the benzofuran unit, with a C12—H12A···Cg2ⁱ separation of 2.74 Å (Table 1 and Fig. 2; Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring; symmetry code as in Fig. 2). Additionally, four different intermolecular C—H···O hydrogen bonds in the structure are observed (Table 1 & Fig. 3).

Related literature top

For the crystal structures of similar alkyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetates, see: Choi et al. (2007, 2008).

Experimental top

77% 3-Chloroperoxybenzoic acid (173 mg, 0.77 mmol) was added in small portions to a stirred solution of propyl 2-(5-chloro-3-methylsulfanyl-1-benzofuran-2-yl)acetate (209 mg, 0.7 mmol) in dichloromethane (20 ml) at 273 K. After being stirred for 3 h at room temperature, 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 (hexane-ethylacetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 80%, m.p. 399–340 K; R_f = 0.51 (hexane-ethyl acetate, 1;2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 0.92 (t, J = 7.30 Hz, 3H), 1.65-1.74 (m, 2H), 3.05 (s, 3H), 4.03 (s, 2H), 4.13 (t, J = 6.92 Hz, 2H), 7.41 (d, J = 8.72 Hz, 1H), 7.50 (dd, J = 8.72 Hz and J = 1.83 Hz, 1H), 8.03 (d, J = 1.82 Hz, 1H); EI-MS 316 [M+2], 314 [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. π—π and C—H···π interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (i) x, y+1, z; (ii) -x, -y+1, -z+2; (iii) x, y-1, z.]
	Fig. 3. Intermolecular C—H···O hydrogen bonds (dotted lines) in the title compound. [Symmetry code: (ii) -x, -y+1, -z+1; (iii) -x, -y+1, -z+2; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y+1, -z+2.]

Propyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₄H₁₅ClO₄S	Z = 2
M_r = 314.77	F(000) = 328
Triclinic, P1	D_x = 1.436 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.528 (2) Å	Cell parameters from 4784 reflections
b = 9.585 (3) Å	θ = 2.4–28.3°
c = 10.195 (3) Å	µ = 0.42 mm⁻¹
α = 73.452 (4)°	T = 173 K
β = 81.773 (5)°	Block, colorless
γ = 65.747 (4)°	0.40 × 0.40 × 0.10 mm
V = 728.0 (4) Å³

Data collection top

Bruker SMART CCD diffractometer	2468 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −11→11
T_min = 0.842, T_max = 0.961	l = −12→12
5062 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0381P)² + 0.4505P] where P = (F_o² + 2F_c²)/3
2468 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₁₅ClO₄S	γ = 65.747 (4)°
M_r = 314.77	V = 728.0 (4) Å³
Triclinic, P1	Z = 2
a = 8.528 (2) Å	Mo Kα radiation
b = 9.585 (3) Å	µ = 0.42 mm⁻¹
c = 10.195 (3) Å	T = 173 K
α = 73.452 (4)°	0.40 × 0.40 × 0.10 mm
β = 81.773 (5)°

Data collection top

Bruker SMART CCD diffractometer	2468 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2304 reflections with I > 2σ(I)
T_min = 0.842, T_max = 0.961	R_int = 0.029
5062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.07	Δρ_max = 0.28 e Å⁻³
2468 reflections	Δρ_min = −0.32 e Å⁻³
182 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
S	0.23799 (6)	0.59458 (6)	0.53751 (4)	0.02410 (15)
Cl	−0.18859 (7)	0.22051 (7)	0.88822 (6)	0.03715 (17)
O1	0.33263 (16)	0.45103 (15)	0.93160 (12)	0.0223 (3)
O2	0.46225 (18)	0.85866 (17)	0.78142 (17)	0.0349 (4)
O3	0.21787 (18)	0.86811 (17)	0.71372 (15)	0.0338 (4)
O4	0.24182 (19)	0.46691 (18)	0.47748 (14)	0.0321 (4)
C1	0.2395 (2)	0.5204 (2)	0.71715 (18)	0.0206 (4)
C2	0.1483 (2)	0.4276 (2)	0.80462 (18)	0.0203 (4)
C3	0.0205 (2)	0.3780 (2)	0.78783 (19)	0.0228 (4)
H3	−0.0289	0.4059	0.7016	0.027*
C4	−0.0300 (2)	0.2866 (2)	0.9031 (2)	0.0249 (4)
C5	0.0395 (3)	0.2434 (2)	1.0326 (2)	0.0266 (4)
H5	0.0019	0.1786	1.1082	0.032*
C6	0.1625 (2)	0.2954 (2)	1.04984 (19)	0.0252 (4)
H6	0.2100	0.2693	1.1366	0.030*
C7	0.2134 (2)	0.3870 (2)	0.93509 (19)	0.0209 (4)
C8	0.3462 (2)	0.5306 (2)	0.79717 (18)	0.0211 (4)
C9	0.4628 (2)	0.6175 (2)	0.76992 (19)	0.0229 (4)
H9A	0.5337	0.5986	0.6860	0.028*
H9B	0.5416	0.5757	0.8470	0.028*
C10	0.3636 (2)	0.7945 (2)	0.75211 (19)	0.0244 (4)
C11	0.3854 (3)	1.0300 (3)	0.7669 (3)	0.0439 (6)
H11A	0.3053	1.0552	0.8453	0.053*
H11B	0.3204	1.0848	0.6815	0.053*
C12	0.5296 (3)	1.0819 (3)	0.7631 (3)	0.0451 (6)
H12A	0.4800	1.1959	0.7603	0.054*
H12B	0.5932	1.0244	0.8489	0.054*
C13	0.6534 (5)	1.0561 (4)	0.6453 (4)	0.0753 (10)
H13A	0.5929	1.1158	0.5596	0.090*
H13B	0.7052	0.9432	0.6478	0.090*
H13C	0.7439	1.0921	0.6509	0.090*
C14	0.0216 (3)	0.7411 (2)	0.5235 (2)	0.0318 (5)
H14A	0.0002	0.8006	0.4277	0.048*
H14B	0.0062	0.8137	0.5798	0.048*
H14C	−0.0595	0.6891	0.5554	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0256 (3)	0.0286 (3)	0.0184 (2)	−0.0127 (2)	−0.00144 (18)	−0.00292 (19)
Cl	0.0348 (3)	0.0380 (3)	0.0473 (3)	−0.0243 (2)	−0.0025 (2)	−0.0075 (2)
O1	0.0237 (7)	0.0252 (7)	0.0198 (6)	−0.0117 (6)	−0.0034 (5)	−0.0035 (5)
O2	0.0254 (8)	0.0228 (7)	0.0590 (10)	−0.0088 (6)	−0.0060 (7)	−0.0128 (7)
O3	0.0249 (8)	0.0292 (8)	0.0437 (9)	−0.0098 (6)	−0.0075 (6)	−0.0019 (7)
O4	0.0341 (8)	0.0393 (8)	0.0260 (7)	−0.0132 (7)	−0.0016 (6)	−0.0143 (6)
C1	0.0228 (9)	0.0198 (9)	0.0190 (9)	−0.0080 (7)	−0.0015 (7)	−0.0047 (7)
C2	0.0211 (9)	0.0173 (9)	0.0207 (9)	−0.0054 (7)	−0.0012 (7)	−0.0053 (7)
C3	0.0234 (10)	0.0217 (9)	0.0254 (10)	−0.0086 (8)	−0.0026 (7)	−0.0085 (8)
C4	0.0214 (10)	0.0210 (10)	0.0346 (11)	−0.0088 (8)	0.0007 (8)	−0.0105 (8)
C5	0.0268 (10)	0.0209 (10)	0.0274 (10)	−0.0088 (8)	0.0031 (8)	−0.0019 (8)
C6	0.0252 (10)	0.0244 (10)	0.0225 (9)	−0.0074 (8)	−0.0020 (8)	−0.0033 (8)
C7	0.0196 (9)	0.0192 (9)	0.0240 (9)	−0.0069 (7)	−0.0013 (7)	−0.0062 (7)
C8	0.0220 (9)	0.0196 (9)	0.0204 (9)	−0.0074 (8)	−0.0004 (7)	−0.0039 (7)
C9	0.0202 (9)	0.0244 (10)	0.0261 (9)	−0.0103 (8)	−0.0015 (7)	−0.0064 (8)
C10	0.0250 (10)	0.0269 (10)	0.0233 (9)	−0.0139 (9)	0.0003 (8)	−0.0039 (8)
C11	0.0322 (12)	0.0236 (11)	0.0760 (18)	−0.0075 (10)	−0.0016 (11)	−0.0177 (11)
C12	0.0357 (13)	0.0242 (11)	0.0760 (18)	−0.0114 (10)	−0.0014 (12)	−0.0139 (11)
C13	0.080 (2)	0.0462 (17)	0.093 (2)	−0.0344 (16)	0.0380 (19)	−0.0128 (16)
C14	0.0314 (11)	0.0270 (11)	0.0325 (11)	−0.0069 (9)	−0.0078 (9)	−0.0043 (9)

Geometric parameters (Å, º) top

S—O4	1.5038 (16)	C6—C7	1.382 (3)
S—C1	1.7656 (18)	C6—H6	0.9500
S—C14	1.797 (2)	C8—C9	1.493 (3)
Cl—C4	1.752 (2)	C9—C10	1.522 (3)
O1—C7	1.379 (2)	C9—H9A	0.9900
O1—C8	1.380 (2)	C9—H9B	0.9900
O2—C10	1.333 (2)	C11—C12	1.496 (3)
O2—C11	1.468 (3)	C11—H11A	0.9900
O3—C10	1.207 (2)	C11—H11B	0.9900
C1—C8	1.354 (3)	C12—C13	1.487 (4)
C1—C2	1.452 (3)	C12—H12A	0.9900
C2—C3	1.403 (3)	C12—H12B	0.9900
C2—C7	1.403 (3)	C13—H13A	0.9800
C3—C4	1.383 (3)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C4—C5	1.407 (3)	C14—H14A	0.9800
C5—C6	1.383 (3)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800

O4—S—C1	106.94 (9)	C10—C9—H9A	109.2
O4—S—C14	106.77 (10)	C8—C9—H9B	109.2
C1—S—C14	98.32 (9)	C10—C9—H9B	109.2
C7—O1—C8	106.32 (14)	H9A—C9—H9B	107.9
C10—O2—C11	116.86 (16)	O3—C10—O2	124.34 (19)
C8—C1—C2	107.36 (16)	O3—C10—C9	125.35 (19)
C8—C1—S	122.84 (15)	O2—C10—C9	110.29 (16)
C2—C1—S	129.51 (15)	O2—C11—C12	107.24 (18)
C3—C2—C7	119.33 (17)	O2—C11—H11A	110.3
C3—C2—C1	136.18 (17)	C12—C11—H11A	110.3
C7—C2—C1	104.48 (17)	O2—C11—H11B	110.3
C4—C3—C2	116.72 (17)	C12—C11—H11B	110.3
C4—C3—H3	121.6	H11A—C11—H11B	108.5
C2—C3—H3	121.6	C13—C12—C11	114.7 (3)
C3—C4—C5	123.34 (19)	C13—C12—H12A	108.6
C3—C4—Cl	118.78 (15)	C11—C12—H12A	108.6
C5—C4—Cl	117.87 (15)	C13—C12—H12B	108.6
C6—C5—C4	119.91 (18)	C11—C12—H12B	108.6
C6—C5—H5	120.0	H12A—C12—H12B	107.6
C4—C5—H5	120.0	C12—C13—H13A	109.5
C7—C6—C5	117.01 (18)	C12—C13—H13B	109.5
C7—C6—H6	121.5	H13A—C13—H13B	109.5
C5—C6—H6	121.5	C12—C13—H13C	109.5
O1—C7—C6	125.69 (17)	H13A—C13—H13C	109.5
O1—C7—C2	110.66 (16)	H13B—C13—H13C	109.5
C6—C7—C2	123.65 (18)	S—C14—H14A	109.5
C1—C8—O1	111.16 (17)	S—C14—H14B	109.5
C1—C8—C9	132.90 (17)	H14A—C14—H14B	109.5
O1—C8—C9	115.80 (16)	S—C14—H14C	109.5
C8—C9—C10	112.11 (15)	H14A—C14—H14C	109.5
C8—C9—H9A	109.2	H14B—C14—H14C	109.5

O4—S—C1—C8	132.24 (16)	C3—C2—C7—O1	−177.81 (15)
C14—S—C1—C8	−117.31 (17)	C1—C2—C7—O1	1.2 (2)
O4—S—C1—C2	−40.91 (19)	C3—C2—C7—C6	2.1 (3)
C14—S—C1—C2	69.54 (19)	C1—C2—C7—C6	−178.94 (17)
C8—C1—C2—C3	178.0 (2)	C2—C1—C8—O1	0.0 (2)
S—C1—C2—C3	−8.0 (3)	S—C1—C8—O1	−174.43 (12)
C8—C1—C2—C7	−0.7 (2)	C2—C1—C8—C9	−175.32 (19)
S—C1—C2—C7	173.25 (14)	S—C1—C8—C9	10.2 (3)
C7—C2—C3—C4	−1.9 (3)	C7—O1—C8—C1	0.7 (2)
C1—C2—C3—C4	179.6 (2)	C7—O1—C8—C9	176.90 (15)
C2—C3—C4—C5	0.3 (3)	C1—C8—C9—C10	72.8 (3)
C2—C3—C4—Cl	−179.76 (13)	O1—C8—C9—C10	−102.43 (18)
C3—C4—C5—C6	1.2 (3)	C11—O2—C10—O3	0.8 (3)
Cl—C4—C5—C6	−178.73 (15)	C11—O2—C10—C9	179.06 (18)
C4—C5—C6—C7	−1.1 (3)	C8—C9—C10—O3	−26.0 (3)
C8—O1—C7—C6	178.95 (18)	C8—C9—C10—O2	155.70 (16)
C8—O1—C7—C2	−1.16 (19)	C10—O2—C11—C12	−163.3 (2)
C5—C6—C7—O1	179.33 (17)	O2—C11—C12—C13	62.5 (3)
C5—C6—C7—C2	−0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cg2ⁱ	0.99	2.74	3.666 (3)	155
C3—H3···O4ⁱⁱ	0.95	2.44	3.353 (2)	160
C5—H5···O3ⁱⁱⁱ	0.95	2.50	3.373 (2)	152
C9—H9A···O4^iv	0.99	2.35	3.321 (2)	166
C9—H9B···O1^v	0.99	2.54	3.489 (2)	161

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅ClO₄S
M_r	314.77
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.528 (2), 9.585 (3), 10.195 (3)
α, β, γ (°)	73.452 (4), 81.773 (5), 65.747 (4)
V (Å³)	728.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.40 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.842, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	5062, 2468, 2304
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.07
No. of reflections	2468
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.32

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
C12—H12A···Cg2ⁱ	0.99	2.74	3.666 (3)	155
C3—H3···O4ⁱⁱ	0.95	2.44	3.353 (2)	160
C5—H5···O3ⁱⁱⁱ	0.95	2.50	3.373 (2)	152
C9—H9A···O4^iv	0.99	2.35	3.321 (2)	166
C9—H9B···O1^v	0.99	2.54	3.489 (2)	161

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

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o3832. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o2139. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. 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 65| Part 3| March 2009| Page o521

doi:10.1107/S1600536809004735

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