3-Methyl­butyl 2-(5-iodo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

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

doi:10.1107/S1600536809011210

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o924

doi:10.1107/S1600536809011210

Open

access

3-Methylbutyl 2-(5-iodo-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 17 March 2009; accepted 26 March 2009; online 31 March 2009)

In the title molecule, C₁₆H₁₉IO₄S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. In the crystal, pairs of molecules are linked by I⋯O [3.114 (3) Å] halogen bonding into centrosymmetric dimers. The crystal structure is further stabilized by weak intermolecular C—H⋯O nonclassical hydrogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see Choi et al. (2009a ,b ). For a review of halogen bonding, see Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₉IO₄S
M_r = 434.27
Monoclinic, P 2₁ /n
a = 10.6726 (9) Å
b = 15.423 (1) Å
c = 10.7343 (9) Å
β = 102.334 (2)°
V = 1726.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.99 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.503, T_max = 0.587 (expected range = 0.472–0.550)
9111 measured reflections
3357 independent reflections
3152 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.079
S = 1.23
3357 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4ⁱ	0.95	2.41	3.310 (5)	159
C16—H16C⋯O3ⁱⁱ	0.98	2.44	3.397 (5)	167
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+2.

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/S1600536809011210/cv2534sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011210/cv2534Isup2.hkl

checkCIF report

Comment top

As a part of our continuing studies on the synthesis and structure of alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, we have recently described the crystal structure of propyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2009a) and butyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2009b). Here we report the crystal structure of the title compound, (I) (Fig. 1).

In (I), the benzofuran unit is essentially planar, with the mean deviation of 0.017 (3) Å from the least-squares plane defined by the nine constituent atoms. Two molecules are linked into centrosymmetric dimer by an I···O halogen bonding (Politzer et al., 2007) between the iodine atom and the oxygen of a neighbouring S═O unit, with an I···O distance of 3.114 (3) Å. The molecular packing (Fig. 2) is stabilized by two intermolecular C—H···O nonclassical hydrogen bonds - between the benzene H atom and the S═O unit, and between the methyl H atom of the methylsulfinyl substituent and the C═O unit, respectively (Fig. 2 and Table 1).

Related literature top

For the crystal structures of similar alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see Choi et al. (2009a,b). For a review of halogen bonding, see Politzer et al. (2007).

Experimental top

The 77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of isoamyl 2-(5-iodo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (434 mg, 1.0 mmol) in dichloromethane (30 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-ethyl acetate,1:2 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 412-413 K; R_f = 0.53 (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 acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 0.91 (d, J = 6.6 Hz, 6H), 1.53 (q, J = 6.6 Hz, 2H), 1.61-1.72 (m, 1H), 3.07 (s, 3H), 4.03 (s, 2H), 4.18 (t, J = 6.96 Hz, 2H), 7.29 (d, J = 8.8 Hz, 1H), 7.66 (dd, J = 8.8 Hz and 1,84 Hz, 1H), 8.28 (d, J = 1.8 Hz, 1H); EI-MS 434 [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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. A portion of the crystal packing of (I) showing the C—H···O hydrogen bonds (dashed lines) and I···O halogen bonding (dotted lines) [symmetry codes: (i) -x+3/2, y+1/2, -z+3/2; (ii) -x+1, -y+1, -z+2; (iii) -x+2, -y+1, -z+2]. H atoms not involved in hydrogen bonding are omitted for clarity.

3-Methylbutyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₆H₁₉IO₄S	F(000) = 864
M_r = 434.27	D_x = 1.671 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7114 reflections
a = 10.6726 (9) Å	θ = 2.4–28.3°
b = 15.423 (1) Å	µ = 1.99 mm⁻¹
c = 10.7343 (9) Å	T = 173 K
β = 102.334 (2)°	Block, colourless
V = 1726.1 (2) Å³	0.40 × 0.40 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3357 independent reflections
Radiation source: fine-focus sealed tube	3152 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.4°
ϕ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→19
T_min = 0.503, T_max = 0.587	l = −12→13
9111 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.079	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.0195P)² + 3.2932P] where P = (F_o² + 2F_c²)/3
3357 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₁₆H₁₉IO₄S	V = 1726.1 (2) Å³
M_r = 434.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6726 (9) Å	µ = 1.99 mm⁻¹
b = 15.423 (1) Å	T = 173 K
c = 10.7343 (9) Å	0.40 × 0.40 × 0.30 mm
β = 102.334 (2)°

Data collection top

Bruker SMART CCD diffractometer	3357 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	3152 reflections with I > 2σ(I)
T_min = 0.503, T_max = 0.587	R_int = 0.026
9111 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.23	Δρ_max = 0.56 e Å⁻³
3357 reflections	Δρ_min = −0.71 e Å⁻³
202 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
I	0.98665 (2)	0.636473 (16)	0.87775 (2)	0.03496 (10)
S	0.60639 (9)	0.32117 (6)	0.94130 (8)	0.0275 (2)
O1	0.4562 (2)	0.47524 (17)	0.6559 (2)	0.0306 (6)
O2	0.1263 (2)	0.34631 (17)	0.6994 (2)	0.0323 (6)
O3	0.2500 (3)	0.43238 (19)	0.8438 (3)	0.0422 (7)
O4	0.7470 (2)	0.30422 (17)	0.9660 (3)	0.0360 (6)
C1	0.5707 (3)	0.4021 (2)	0.8231 (3)	0.0248 (7)
C2	0.6445 (3)	0.4775 (2)	0.8026 (3)	0.0241 (7)
C3	0.7649 (3)	0.5115 (2)	0.8584 (3)	0.0244 (7)
H3	0.8189	0.4845	0.9296	0.029*
C4	0.8018 (3)	0.5868 (2)	0.8045 (3)	0.0281 (7)
C5	0.7231 (4)	0.6290 (2)	0.7033 (4)	0.0311 (8)
H5	0.7515	0.6812	0.6713	0.037*
C6	0.6029 (4)	0.5957 (2)	0.6480 (3)	0.0323 (8)
H6	0.5475	0.6239	0.5788	0.039*
C7	0.5685 (3)	0.5196 (2)	0.6990 (3)	0.0275 (8)
C8	0.4610 (3)	0.4037 (2)	0.7323 (3)	0.0290 (8)
C9	0.3470 (3)	0.3461 (3)	0.7034 (4)	0.0329 (9)
H9A	0.3707	0.2879	0.7398	0.040*
H9B	0.3185	0.3399	0.6099	0.040*
C10	0.2375 (3)	0.3817 (2)	0.7578 (3)	0.0285 (8)
C11	0.0149 (4)	0.3741 (3)	0.7474 (4)	0.0439 (10)
H11A	0.0056	0.4379	0.7412	0.053*
H11B	0.0246	0.3571	0.8379	0.053*
C12	−0.1006 (4)	0.3307 (3)	0.6670 (4)	0.0366 (9)
H12A	−0.1757	0.3436	0.7042	0.044*
H12B	−0.0868	0.2672	0.6724	0.044*
C13	−0.1330 (4)	0.3561 (3)	0.5274 (4)	0.0409 (10)
H13	−0.0564	0.3437	0.4905	0.049*
C14	−0.2427 (5)	0.2997 (4)	0.4585 (6)	0.080 (2)
H14A	−0.2175	0.2385	0.4684	0.120*
H14B	−0.2631	0.3147	0.3677	0.120*
H14C	−0.3183	0.3093	0.4949	0.120*
C15	−0.1639 (5)	0.4518 (4)	0.5093 (5)	0.0607 (14)
H15A	−0.2415	0.4649	0.5408	0.091*
H15B	−0.1781	0.4664	0.4185	0.091*
H15C	−0.0921	0.4861	0.5570	0.091*
C16	0.5774 (4)	0.3837 (3)	1.0723 (4)	0.0367 (9)
H16A	0.5952	0.3483	1.1499	0.055*
H16B	0.4876	0.4025	1.0546	0.055*
H16C	0.6335	0.4347	1.0844	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.03406 (15)	0.03270 (15)	0.03724 (15)	−0.01078 (10)	0.00567 (10)	0.00262 (11)
S	0.0287 (5)	0.0217 (4)	0.0313 (4)	−0.0019 (3)	0.0046 (4)	−0.0022 (3)
O1	0.0250 (13)	0.0389 (14)	0.0249 (12)	0.0014 (11)	−0.0010 (10)	−0.0019 (11)
O2	0.0220 (12)	0.0414 (15)	0.0322 (13)	0.0005 (11)	0.0032 (10)	−0.0092 (11)
O3	0.0378 (16)	0.0473 (17)	0.0421 (16)	−0.0048 (13)	0.0102 (13)	−0.0208 (14)
O4	0.0285 (14)	0.0327 (14)	0.0448 (16)	0.0031 (11)	0.0030 (12)	0.0004 (12)
C1	0.0253 (17)	0.0234 (17)	0.0256 (17)	0.0004 (14)	0.0052 (14)	−0.0033 (14)
C2	0.0240 (17)	0.0256 (17)	0.0232 (16)	0.0027 (14)	0.0062 (13)	−0.0033 (13)
C3	0.0236 (17)	0.0273 (17)	0.0215 (16)	0.0013 (14)	0.0034 (13)	0.0009 (13)
C4	0.0275 (18)	0.0285 (18)	0.0283 (18)	0.0008 (15)	0.0059 (14)	−0.0023 (15)
C5	0.038 (2)	0.0248 (18)	0.0326 (19)	0.0008 (15)	0.0128 (16)	0.0011 (15)
C6	0.040 (2)	0.0325 (19)	0.0228 (17)	0.0080 (17)	0.0028 (15)	0.0014 (15)
C7	0.0287 (19)	0.0304 (18)	0.0229 (16)	0.0034 (15)	0.0046 (14)	−0.0019 (14)
C8	0.0261 (18)	0.0315 (19)	0.0292 (18)	0.0029 (15)	0.0051 (14)	−0.0072 (15)
C9	0.0237 (18)	0.035 (2)	0.039 (2)	−0.0035 (15)	0.0030 (16)	−0.0122 (16)
C10	0.0270 (18)	0.0294 (18)	0.0273 (17)	0.0008 (15)	0.0019 (14)	0.0000 (15)
C11	0.030 (2)	0.064 (3)	0.039 (2)	0.008 (2)	0.0081 (17)	−0.009 (2)
C12	0.0242 (19)	0.042 (2)	0.045 (2)	0.0004 (17)	0.0108 (17)	−0.0001 (18)
C13	0.035 (2)	0.046 (2)	0.040 (2)	0.0111 (19)	0.0043 (18)	−0.0060 (19)
C14	0.048 (3)	0.091 (5)	0.089 (4)	0.002 (3)	−0.014 (3)	−0.037 (4)
C15	0.059 (3)	0.065 (3)	0.058 (3)	0.025 (3)	0.014 (3)	0.015 (3)
C16	0.049 (2)	0.034 (2)	0.0293 (19)	0.0004 (18)	0.0129 (17)	−0.0031 (16)

Geometric parameters (Å, º) top

I—C4	2.106 (4)	C9—C10	1.515 (5)
I—O4ⁱ	3.114 (3)	C9—H9A	0.9900
S—O4	1.490 (3)	C9—H9B	0.9900
S—C1	1.762 (4)	C11—C12	1.503 (6)
S—C16	1.786 (4)	C11—H11A	0.9900
O1—C8	1.369 (5)	C11—H11B	0.9900
O1—C7	1.372 (4)	C12—C13	1.516 (6)
O2—C10	1.335 (4)	C12—H12A	0.9900
O2—C11	1.457 (5)	C12—H12B	0.9900
O3—C10	1.195 (4)	C13—C15	1.517 (6)
C1—C8	1.355 (5)	C13—C14	1.518 (7)
C1—C2	1.448 (5)	C13—H13	1.0000
C2—C7	1.390 (5)	C14—H14A	0.9800
C2—C3	1.398 (5)	C14—H14B	0.9800
C3—C4	1.391 (5)	C14—H14C	0.9800
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.386 (5)	C15—H15B	0.9800
C5—C6	1.392 (5)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.379 (5)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C8—C9	1.484 (5)

C4—I—O4ⁱ	169.4 (1)	O2—C10—C9	110.6 (3)
O4—S—C1	107.9 (2)	O2—C11—C12	107.3 (3)
O4—S—C16	107.0 (2)	O2—C11—H11A	110.3
C1—S—C16	97.9 (2)	C12—C11—H11A	110.3
C8—O1—C7	106.4 (3)	O2—C11—H11B	110.3
C10—O2—C11	115.1 (3)	C12—C11—H11B	110.3
C8—C1—C2	106.9 (3)	H11A—C11—H11B	108.5
C8—C1—S	123.5 (3)	C11—C12—C13	116.0 (4)
C2—C1—S	129.6 (3)	C11—C12—H12A	108.3
C7—C2—C3	119.6 (3)	C13—C12—H12A	108.3
C7—C2—C1	104.6 (3)	C11—C12—H12B	108.3
C3—C2—C1	135.8 (3)	C13—C12—H12B	108.3
C4—C3—C2	116.8 (3)	H12A—C12—H12B	107.4
C4—C3—H3	121.6	C12—C13—C15	112.1 (4)
C2—C3—H3	121.6	C12—C13—C14	108.8 (4)
C5—C4—C3	122.7 (3)	C15—C13—C14	111.8 (4)
C5—C4—I	119.0 (3)	C12—C13—H13	108.0
C3—C4—I	118.3 (3)	C15—C13—H13	108.0
C4—C5—C6	120.7 (3)	C14—C13—H13	108.0
C4—C5—H5	119.6	C13—C14—H14A	109.5
C6—C5—H5	119.6	C13—C14—H14B	109.5
C7—C6—C5	116.3 (3)	H14A—C14—H14B	109.5
C7—C6—H6	121.8	C13—C14—H14C	109.5
C5—C6—H6	121.8	H14A—C14—H14C	109.5
O1—C7—C6	125.3 (3)	H14B—C14—H14C	109.5
O1—C7—C2	110.9 (3)	C13—C15—H15A	109.5
C6—C7—C2	123.8 (3)	C13—C15—H15B	109.5
C1—C8—O1	111.2 (3)	H15A—C15—H15B	109.5
C1—C8—C9	133.1 (4)	C13—C15—H15C	109.5
O1—C8—C9	115.7 (3)	H15A—C15—H15C	109.5
C8—C9—C10	111.6 (3)	H15B—C15—H15C	109.5
C8—C9—H9A	109.3	S—C16—H16A	109.5
C10—C9—H9A	109.3	S—C16—H16B	109.5
C8—C9—H9B	109.3	H16A—C16—H16B	109.5
C10—C9—H9B	109.3	S—C16—H16C	109.5
H9A—C9—H9B	108.0	H16A—C16—H16C	109.5
O3—C10—O2	124.8 (4)	H16B—C16—H16C	109.5
O3—C10—C9	124.5 (3)

O4—S—C1—C8	144.4 (3)	C3—C2—C7—O1	178.4 (3)
C16—S—C1—C8	−104.9 (3)	C1—C2—C7—O1	−0.3 (4)
O4—S—C1—C2	−36.8 (4)	C3—C2—C7—C6	−1.8 (5)
C16—S—C1—C2	74.0 (4)	C1—C2—C7—C6	179.5 (3)
C8—C1—C2—C7	1.0 (4)	C2—C1—C8—O1	−1.3 (4)
S—C1—C2—C7	−178.0 (3)	S—C1—C8—O1	177.8 (2)
C8—C1—C2—C3	−177.4 (4)	C2—C1—C8—C9	−179.0 (4)
S—C1—C2—C3	3.6 (6)	S—C1—C8—C9	0.0 (6)
C7—C2—C3—C4	−0.4 (5)	C7—O1—C8—C1	1.1 (4)
C1—C2—C3—C4	177.7 (4)	C7—O1—C8—C9	179.3 (3)
C2—C3—C4—C5	2.2 (5)	C1—C8—C9—C10	98.3 (5)
C2—C3—C4—I	−176.4 (2)	O1—C8—C9—C10	−79.4 (4)
O4ⁱ—I—C4—C5	149.4 (5)	C11—O2—C10—O3	0.4 (5)
O4ⁱ—I—C4—C3	−31.9 (8)	C11—O2—C10—C9	178.1 (3)
C3—C4—C5—C6	−1.9 (6)	C8—C9—C10—O3	−21.8 (6)
I—C4—C5—C6	176.7 (3)	C8—C9—C10—O2	160.4 (3)
C4—C5—C6—C7	−0.3 (5)	C10—O2—C11—C12	177.6 (3)
C8—O1—C7—C6	179.7 (3)	O2—C11—C12—C13	−64.3 (5)
C8—O1—C7—C2	−0.4 (4)	C11—C12—C13—C15	−61.6 (5)
C5—C6—C7—O1	−178.1 (3)	C11—C12—C13—C14	174.2 (4)
C5—C6—C7—C2	2.1 (5)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱⁱ	0.95	2.41	3.310 (5)	159
C16—H16C···O3ⁱⁱⁱ	0.98	2.44	3.397 (5)	167

Symmetry codes: (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉IO₄S
M_r	434.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	10.6726 (9), 15.423 (1), 10.7343 (9)
β (°)	102.334 (2)
V (Å³)	1726.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.99
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.503, 0.587
No. of measured, independent and observed [I > 2σ(I)] reflections	9111, 3357, 3152
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.079, 1.23
No. of reflections	3357
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.71

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
C5—H5···O4ⁱ	0.95	2.41	3.310 (5)	159.2
C16—H16C···O3ⁱⁱ	0.98	2.44	3.397 (5)	166.7

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −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. (2009a). Acta Cryst. E65, o151. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o266. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o924

doi:10.1107/S1600536809011210

Open

access