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

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

doi:10.1107/S1600536808042359

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o151

doi:10.1107/S1600536808042359

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Propyl 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 8 December 2008; accepted 12 December 2008; online 17 December 2008)

In the title compound, C₁₄H₁₅IO₄S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by intermolecular C—H⋯π interactions between an H atom of the propyl methylene group closest to the carboxylate O atom and the benzene ring of a neighbouring molecule, and between an H atom of the outer propyl methylene group and the furan ring of a neighbouring molecule, respectively. Additionally, the crystal structure exhibits intermolecular C—H⋯O hydrogen bonds.

Related literature

For the synthesis and crystal structures of similar alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₄H₁₅IO₄S
M_r = 406.22
Triclinic, $[P \overline 1]$
a = 8.5468 (4) Å
b = 10.0329 (5) Å
c = 10.3239 (5) Å
α = 72.442 (1)°
β = 81.345 (1)°
γ = 65.088 (1)°
V = 765.21 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.24 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.583, T_max = 0.787
6182 measured reflections
2982 independent reflections
2778 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 1.18
2982 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1ⁱ	0.97	3.12	3.814 (4)	130
C12—H12B⋯Cg2ⁱⁱ	0.97	2.99	3.929 (3)	162
C3—H3⋯O4ⁱⁱⁱ	0.93	2.60	3.468 (4)	157
C9—H9B⋯O4^iv	0.97	2.40	3.356 (4)	167
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+2; (iv) -x, -y+1, -z+2. Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.

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/S1600536808042359/sj2566sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042359/sj2566Isup2.hkl

checkCIF report

Comment top

This work is related to our previous communications on the synthesis and structure of alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. ethyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2007) and isopropyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008). Here we report the crystal structure of the title compound, propyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.012 (2) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by intermolecular C—H···π interactions within each stack of molecules; one between the hydrogen of 11–methylene group and the benzene ring of the benzofuran unit, with a C11—H11B···Cg1ⁱ separation of 3.12 Å, and a second between the hydrogen of 12-methylene group and the furan ring of the benzofuran unit, with a C12—H12B···Cg2ⁱ with a separation of 2.99 Å (Table 1 and Fig. 2; Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively, symmetry code as in Fig. 2). In addition, intermolecular C—H···O hydrogen bonds in the structure are observed (Table 1).

Related literature top

For the synthesis and crystal structures of similar alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2007, 2008). Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively

Experimental top

77% 3-chloroperoxybenzoic acid (173 mg, 0.77 mmol) was added in small portions to a stirred solution of propyl 2-(5-iodo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (273 mg, 0.7 mmol) in dichloromethane (30 ml) at 273 K. After stirring 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 80%, m.p. 412-413 K; R_f = 0.58 (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 0.93 (t, J = 7.36 Hz, 3H), 1.64-1.72 (m, 2H), 3.07 (s, 3H), 4.02 (s, 2H), 4.11 (t, J = 6.60 Hz, 2H), 7.29 (d, J = 8.76 Hz, 1H), 7.66 (dd, J = 8.80 Hz and J = 1.84 Hz, 1H), 8.28 (d, J = 1.48 Hz, 1H); EI-MS 406 [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 30% probability level.
	Fig. 2. 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.]

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

Crystal data top

C₁₄H₁₅IO₄S	Z = 2
M_r = 406.22	F(000) = 400
Triclinic, P1	D_x = 1.763 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5468 (4) Å	Cell parameters from 4625 reflections
b = 10.0329 (5) Å	θ = 2.3–28.3°
c = 10.3239 (5) Å	µ = 2.24 mm⁻¹
α = 72.442 (1)°	T = 293 K
β = 81.345 (1)°	Plate, colorless
γ = 65.088 (1)°	0.30 × 0.20 × 0.10 mm
V = 765.21 (6) Å³

Data collection top

Bruker SMART CCD diffractometer	2982 independent reflections
Radiation source: fine-focus sealed tube	2778 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
T_min = 0.583, T_max = 0.787	l = −12→12
6182 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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F²) = 0.069	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0293P)² + 0.5734P] where P = (F_o² + 2F_c²)/3
2982 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₄H₁₅IO₄S	γ = 65.088 (1)°
M_r = 406.22	V = 765.21 (6) Å³
Triclinic, P1	Z = 2
a = 8.5468 (4) Å	Mo Kα radiation
b = 10.0329 (5) Å	µ = 2.24 mm⁻¹
c = 10.3239 (5) Å	T = 293 K
α = 72.442 (1)°	0.30 × 0.20 × 0.10 mm
β = 81.345 (1)°

Data collection top

Bruker SMART CCD diffractometer	2982 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2778 reflections with I > 2σ(I)
T_min = 0.583, T_max = 0.787	R_int = 0.016
6182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.18	Δρ_max = 0.52 e Å⁻³
2982 reflections	Δρ_min = −0.56 e Å⁻³
183 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	0.69366 (3)	0.79269 (3)	0.61486 (2)	0.04832 (10)
S	0.26183 (10)	0.40380 (10)	0.96397 (8)	0.03932 (18)
O1	0.1660 (3)	0.5368 (2)	0.5730 (2)	0.0350 (4)
O2	0.0455 (3)	0.1416 (3)	0.7355 (3)	0.0530 (6)
O3	0.2911 (3)	0.1379 (3)	0.7896 (3)	0.0567 (7)
O4	0.2582 (3)	0.5257 (3)	1.0206 (2)	0.0529 (6)
C1	0.2539 (4)	0.4770 (3)	0.7857 (3)	0.0337 (6)
C2	0.3414 (4)	0.5677 (3)	0.6976 (3)	0.0303 (6)
C3	0.4622 (4)	0.6215 (3)	0.7127 (3)	0.0335 (6)
H3	0.5072	0.5992	0.7969	0.040*
C4	0.5121 (4)	0.7091 (3)	0.5973 (3)	0.0340 (6)
C5	0.4466 (4)	0.7459 (3)	0.4690 (3)	0.0387 (7)
H5	0.4825	0.8069	0.3943	0.046*
C6	0.3287 (4)	0.6913 (3)	0.4533 (3)	0.0368 (7)
H6	0.2844	0.7134	0.3689	0.044*
C7	0.2796 (4)	0.6029 (3)	0.5682 (3)	0.0322 (6)
C8	0.1529 (4)	0.4619 (3)	0.7075 (3)	0.0330 (6)
C9	0.0405 (4)	0.3755 (3)	0.7359 (3)	0.0367 (7)
H9A	−0.0360	0.4135	0.6606	0.044*
H9B	−0.0303	0.3929	0.8168	0.044*
C10	0.1438 (4)	0.2060 (4)	0.7564 (3)	0.0396 (7)
C11	0.1272 (5)	−0.0221 (4)	0.7496 (6)	0.0702 (13)
H11A	0.1879	−0.0747	0.8343	0.084*
H11B	0.2094	−0.0435	0.6752	0.084*
C12	−0.0126 (6)	−0.0740 (5)	0.7479 (5)	0.0683 (12)
H12A	−0.0746	−0.0170	0.6641	0.082*
H12B	0.0396	−0.1808	0.7486	0.082*
C13	−0.1370 (9)	−0.0548 (7)	0.8641 (6)	0.102 (2)
H13A	−0.0787	−0.1189	0.9471	0.154*
H13B	−0.2278	−0.0829	0.8536	0.154*
H13C	−0.1850	0.0497	0.8670	0.154*
C14	0.4798 (5)	0.2651 (4)	0.9739 (4)	0.0539 (9)
H14A	0.5572	0.3159	0.9444	0.081*
H14B	0.4958	0.2005	0.9166	0.081*
H14C	0.5031	0.2045	1.0661	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.04655 (14)	0.04768 (14)	0.05934 (16)	−0.02881 (11)	−0.00540 (10)	−0.00948 (10)
S	0.0427 (4)	0.0487 (4)	0.0301 (4)	−0.0235 (4)	−0.0015 (3)	−0.0075 (3)
O1	0.0358 (11)	0.0404 (11)	0.0329 (11)	−0.0184 (9)	−0.0071 (8)	−0.0077 (9)
O2	0.0399 (12)	0.0362 (12)	0.0874 (19)	−0.0165 (10)	−0.0083 (12)	−0.0177 (12)
O3	0.0393 (13)	0.0466 (14)	0.0806 (19)	−0.0156 (11)	−0.0146 (12)	−0.0079 (13)
O4	0.0619 (16)	0.0638 (16)	0.0409 (13)	−0.0264 (13)	−0.0003 (11)	−0.0234 (12)
C1	0.0349 (15)	0.0350 (15)	0.0336 (15)	−0.0152 (13)	−0.0026 (12)	−0.0098 (12)
C2	0.0314 (14)	0.0304 (14)	0.0297 (14)	−0.0112 (12)	−0.0026 (11)	−0.0099 (11)
C3	0.0360 (15)	0.0335 (15)	0.0339 (16)	−0.0142 (12)	−0.0052 (12)	−0.0104 (12)
C4	0.0316 (15)	0.0311 (14)	0.0419 (16)	−0.0131 (12)	−0.0016 (12)	−0.0119 (13)
C5	0.0400 (17)	0.0335 (15)	0.0377 (16)	−0.0138 (13)	0.0009 (13)	−0.0049 (13)
C6	0.0392 (16)	0.0395 (16)	0.0301 (15)	−0.0150 (13)	−0.0048 (12)	−0.0062 (13)
C7	0.0299 (14)	0.0311 (14)	0.0378 (15)	−0.0111 (12)	−0.0053 (12)	−0.0118 (12)
C8	0.0339 (15)	0.0320 (15)	0.0335 (15)	−0.0142 (12)	−0.0027 (12)	−0.0070 (12)
C9	0.0343 (15)	0.0412 (16)	0.0410 (17)	−0.0188 (13)	−0.0023 (13)	−0.0134 (13)
C10	0.0397 (17)	0.0422 (17)	0.0403 (17)	−0.0220 (14)	0.0007 (13)	−0.0082 (14)
C11	0.051 (2)	0.038 (2)	0.122 (4)	−0.0153 (17)	−0.001 (2)	−0.027 (2)
C12	0.063 (3)	0.043 (2)	0.105 (4)	−0.0231 (19)	−0.004 (2)	−0.026 (2)
C13	0.124 (5)	0.100 (4)	0.111 (5)	−0.078 (4)	0.044 (4)	−0.040 (4)
C14	0.051 (2)	0.055 (2)	0.049 (2)	−0.0147 (17)	−0.0128 (16)	−0.0084 (17)

Geometric parameters (Å, º) top

I—C4	2.102 (3)	C6—C7	1.379 (4)
S—O4	1.494 (3)	C6—H6	0.9300
S—C1	1.764 (3)	C8—C9	1.491 (4)
S—C14	1.790 (4)	C9—C10	1.513 (4)
O1—C7	1.375 (3)	C9—H9A	0.9700
O1—C8	1.378 (3)	C9—H9B	0.9700
O2—C10	1.329 (4)	C11—C12	1.495 (6)
O2—C11	1.458 (4)	C11—H11A	0.9700
O3—C10	1.197 (4)	C11—H11B	0.9700
C1—C8	1.347 (4)	C12—C13	1.480 (7)
C1—C2	1.443 (4)	C12—H12A	0.9700
C2—C3	1.397 (4)	C12—H12B	0.9700
C2—C7	1.399 (4)	C13—H13A	0.9600
C3—C4	1.380 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.400 (4)	C14—H14A	0.9600
C5—C6	1.381 (4)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600

O4—S—C1	106.92 (14)	C10—C9—H9A	109.1
O4—S—C14	106.66 (17)	C8—C9—H9B	109.1
C1—S—C14	98.06 (16)	C10—C9—H9B	109.1
C7—O1—C8	106.0 (2)	H9A—C9—H9B	107.9
C10—O2—C11	116.8 (3)	O3—C10—O2	124.3 (3)
C8—C1—C2	107.3 (3)	O3—C10—C9	125.7 (3)
C8—C1—S	123.9 (2)	O2—C10—C9	110.0 (3)
C2—C1—S	128.7 (2)	O2—C11—C12	107.4 (3)
C3—C2—C7	119.1 (3)	O2—C11—H11A	110.2
C3—C2—C1	136.3 (3)	C12—C11—H11A	110.2
C7—C2—C1	104.6 (2)	O2—C11—H11B	110.2
C4—C3—C2	117.2 (3)	C12—C11—H11B	110.2
C4—C3—H3	121.4	H11A—C11—H11B	108.5
C2—C3—H3	121.4	C13—C12—C11	113.5 (4)
C3—C4—C5	123.1 (3)	C13—C12—H12A	108.9
C3—C4—I	118.6 (2)	C11—C12—H12A	108.9
C5—C4—I	118.3 (2)	C13—C12—H12B	108.9
C6—C5—C4	119.9 (3)	C11—C12—H12B	108.9
C6—C5—H5	120.1	H12A—C12—H12B	107.7
C4—C5—H5	120.1	C12—C13—H13A	109.5
C7—C6—C5	117.2 (3)	C12—C13—H13B	109.5
C7—C6—H6	121.4	H13A—C13—H13B	109.5
C5—C6—H6	121.4	C12—C13—H13C	109.5
O1—C7—C6	125.8 (3)	H13A—C13—H13C	109.5
O1—C7—C2	110.7 (3)	H13B—C13—H13C	109.5
C6—C7—C2	123.6 (3)	S—C14—H14A	109.5
C1—C8—O1	111.4 (3)	S—C14—H14B	109.5
C1—C8—C9	133.3 (3)	H14A—C14—H14B	109.5
O1—C8—C9	115.2 (2)	S—C14—H14C	109.5
C8—C9—C10	112.3 (2)	H14A—C14—H14C	109.5
C8—C9—H9A	109.1	H14B—C14—H14C	109.5

O4—S—C1—C8	−135.7 (3)	C3—C2—C7—O1	178.3 (2)
C14—S—C1—C8	114.1 (3)	C1—C2—C7—O1	−1.5 (3)
O4—S—C1—C2	40.8 (3)	C3—C2—C7—C6	−1.4 (4)
C14—S—C1—C2	−69.4 (3)	C1—C2—C7—C6	178.8 (3)
C8—C1—C2—C3	−178.7 (3)	C2—C1—C8—O1	−0.3 (3)
S—C1—C2—C3	4.4 (5)	S—C1—C8—O1	176.8 (2)
C8—C1—C2—C7	1.0 (3)	C2—C1—C8—C9	175.8 (3)
S—C1—C2—C7	−175.9 (2)	S—C1—C8—C9	−7.1 (5)
C7—C2—C3—C4	0.8 (4)	C7—O1—C8—C1	−0.6 (3)
C1—C2—C3—C4	−179.4 (3)	C7—O1—C8—C9	−177.5 (2)
C2—C3—C4—C5	0.4 (4)	C1—C8—C9—C10	−74.2 (4)
C2—C3—C4—I	−180.0 (2)	O1—C8—C9—C10	101.8 (3)
C3—C4—C5—C6	−1.2 (5)	C11—O2—C10—O3	−2.4 (5)
I—C4—C5—C6	179.2 (2)	C11—O2—C10—C9	179.2 (3)
C4—C5—C6—C7	0.7 (4)	C8—C9—C10—O3	22.6 (5)
C8—O1—C7—C6	−179.0 (3)	C8—C9—C10—O2	−159.0 (3)
C8—O1—C7—C2	1.3 (3)	C10—O2—C11—C12	169.5 (4)
C5—C6—C7—O1	−179.1 (3)	O2—C11—C12—C13	−63.9 (6)
C5—C6—C7—C2	0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1ⁱ	0.97	3.12	3.814 (4)	130
C12—H12B···Cg2ⁱⁱ	0.97	2.99	3.929 (3)	162
C3—H3···O4ⁱⁱⁱ	0.93	2.60	3.468 (4)	157
C9—H9B···O4^iv	0.97	2.40	3.356 (4)	167

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅IO₄S
M_r	406.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5468 (4), 10.0329 (5), 10.3239 (5)
α, β, γ (°)	72.442 (1), 81.345 (1), 65.088 (1)
V (Å³)	765.21 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.24
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.583, 0.787
No. of measured, independent and observed [I > 2σ(I)] reflections	6182, 2982, 2778
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.18
No. of reflections	2982
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.56

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
C11—H11B···Cg1ⁱ	0.97	3.12	3.814 (4)	129.7
C12—H12B···Cg2ⁱⁱ	0.97	2.99	3.929 (3)	162.4
C3—H3···O4ⁱⁱⁱ	0.93	2.60	3.468 (4)	156.5
C9—H9B···O4^iv	0.97	2.40	3.356 (4)	166.5

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+2; (iv) −x, −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, o4081. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o2384. 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 1| January 2009| Page o151

doi:10.1107/S1600536808042359

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