5-Bromo-3-(4-fluoro­phenyl­sulfon­yl)-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536812043607

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3208

doi:10.1107/S1600536812043607

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5-Bromo-3-(4-fluorophenylsulfonyl)-2,7-dimethyl-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 15 October 2012; accepted 21 October 2012; online 27 October 2012)

In the title compound, C₁₆H₁₂BrFO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.35 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked into [010] chains via two different inversion-generated pairs of C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.667 (2) Å and slippage = 1.341 (2) Å], and between the benzene and the furan rings of neighbouring molecules [centroid–centroid distance = 3.759 (2) Å and slippage = 0.757 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 , 2012 ).

Experimental

Crystal data

C₁₆H₁₂BrFO₃S
M_r = 383.23
Triclinic, $[P \overline 1]$
a = 8.0789 (1) Å
b = 9.2754 (2) Å
c = 11.3555 (2) Å
α = 71.283 (1)°
β = 72.645 (1)°
γ = 70.042 (1)°
V = 740.30 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.94 mm⁻¹
T = 173 K
0.29 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.527, T_max = 0.746
14090 measured reflections
3680 independent reflections
3259 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 1.02
3680 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.95	2.53	3.408 (2)	154
C9—H9A⋯O2ⁱⁱ	0.98	2.50	3.304 (2)	139
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

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/S1600536812043607/hb6977sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043607/hb6977Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043607/hb6977Isup3.cml

checkCIF report

Comment top

As a part of our continuing study of 5-bromo-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010) and 4-methylphenylsulfonyl (Choi et al., 2012) substituents in 3-position, 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 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-fluorophenyl ring and the mean plane of the benzofuran ring is 72.35 (5). In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···O hydrogen bonds (Table 1), forming inversion dimers. The crystal packing (Fig. 2) also exhibits slipped π–π interactions; the first one between the benzene rings of neighbouring molecules, with a Cg1···Cg1ⁱⁱⁱ distance of 3.667 (2) Å and an interplanar distance of 3.413 (2) Å resulting in a slippage of 1.341 (2) Å (Cg1 is the centroid of the C2–C7 benzene ring), and the second one between the benzene and the furan rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱ distance of 3.759 (2) Å and an interplanar distance of 3.682 (2) Å resulting in a slippage of 0.757 (2) Å (Cg2 is the C1/C2/C7/O1/C8 furan ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2,7-dimethyl-1-benzofuran (281 mg, 0.8 mmol) in dichloromethane (40 ml) at 273 K. After being stirred at room temperature for 10h, 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 71%, m.p. 472–473 K; R_f = 0.57 (hexane–ethyl acetate, 4:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

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 displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	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 + 1, - z + 1; (ii) - x + 1, - y, - z + 1; (iii) - x + 2, - y, - z + 1.]

5-Bromo-3-(4-fluorophenylsulfonyl)-2,7-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₂BrFO₃S	Z = 2
M_r = 383.23	F(000) = 384
Triclinic, P1	D_x = 1.719 Mg m⁻³
Hall symbol: -P 1	Melting point = 472–473 K
a = 8.0789 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2754 (2) Å	Cell parameters from 6655 reflections
c = 11.3555 (2) Å	θ = 2.7–28.3°
α = 71.283 (1)°	µ = 2.94 mm⁻¹
β = 72.645 (1)°	T = 173 K
γ = 70.042 (1)°	Block, colourless
V = 740.30 (2) Å³	0.29 × 0.21 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3680 independent reflections
Radiation source: rotating anode	3259 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.031
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.9°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.527, T_max = 0.746	l = −15→15
14090 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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F²) = 0.074	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0417P)² + 0.237P] where P = (F_o² + 2F_c²)/3
3680 reflections	(Δ/σ)_max = 0.002
201 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₆H₁₂BrFO₃S	γ = 70.042 (1)°
M_r = 383.23	V = 740.30 (2) Å³
Triclinic, P1	Z = 2
a = 8.0789 (1) Å	Mo Kα radiation
b = 9.2754 (2) Å	µ = 2.94 mm⁻¹
c = 11.3555 (2) Å	T = 173 K
α = 71.283 (1)°	0.29 × 0.21 × 0.18 mm
β = 72.645 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3680 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3259 reflections with I > 2σ(I)
T_min = 0.527, T_max = 0.746	R_int = 0.031
14090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
3680 reflections	Δρ_min = −0.47 e Å⁻³
201 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
Br1	0.75349 (3)	0.10966 (3)	0.797351 (17)	0.03912 (8)
S1	0.48725 (5)	0.40486 (5)	0.29104 (4)	0.02342 (10)
F1	1.00247 (19)	0.77090 (18)	0.00357 (14)	0.0571 (4)
O1	0.75109 (17)	−0.04433 (15)	0.32764 (12)	0.0274 (3)
O2	0.40458 (16)	0.45572 (16)	0.40738 (11)	0.0286 (3)
O3	0.37705 (17)	0.41993 (16)	0.20642 (12)	0.0315 (3)
C1	0.6075 (2)	0.2081 (2)	0.33360 (16)	0.0242 (3)
C2	0.6733 (2)	0.1303 (2)	0.45008 (15)	0.0227 (3)
C3	0.6674 (2)	0.1745 (2)	0.55829 (16)	0.0251 (3)
H3	0.6078	0.2785	0.5692	0.030*
C4	0.7538 (2)	0.0574 (2)	0.64843 (16)	0.0271 (3)
C5	0.8430 (2)	−0.0963 (2)	0.63592 (17)	0.0285 (4)
H5	0.9010	−0.1707	0.7011	0.034*
C6	0.8486 (2)	−0.1426 (2)	0.52969 (17)	0.0268 (3)
C7	0.7611 (2)	−0.0248 (2)	0.44028 (16)	0.0243 (3)
C8	0.6581 (2)	0.0987 (2)	0.26428 (16)	0.0265 (3)
C9	0.9424 (3)	−0.3065 (2)	0.51205 (19)	0.0331 (4)
H9A	0.8612	−0.3460	0.4891	0.050*
H9B	0.9767	−0.3761	0.5915	0.050*
H9C	1.0506	−0.3045	0.4440	0.050*
C10	0.6362 (3)	0.1018 (3)	0.13857 (18)	0.0346 (4)
H10A	0.5784	0.2103	0.0967	0.052*
H10B	0.5610	0.0329	0.1499	0.052*
H10C	0.7547	0.0644	0.0858	0.052*
C11	0.6478 (2)	0.5107 (2)	0.20442 (16)	0.0244 (3)
C12	0.6821 (3)	0.5500 (2)	0.07255 (17)	0.0321 (4)
H12	0.6237	0.5157	0.0295	0.038*
C13	0.8014 (3)	0.6392 (3)	0.00442 (19)	0.0394 (5)
H13	0.8256	0.6685	−0.0859	0.047*
C14	0.8840 (3)	0.6845 (2)	0.0705 (2)	0.0376 (4)
C15	0.8550 (3)	0.6459 (3)	0.2007 (2)	0.0370 (4)
H15	0.9169	0.6782	0.2427	0.044*
C16	0.7330 (2)	0.5585 (2)	0.26933 (17)	0.0300 (4)
H16	0.7078	0.5316	0.3597	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.05355 (14)	0.04150 (14)	0.02493 (11)	−0.01030 (10)	−0.01583 (8)	−0.00744 (8)
S1	0.02474 (19)	0.0241 (2)	0.02165 (19)	−0.00430 (16)	−0.00808 (15)	−0.00546 (16)
F1	0.0558 (8)	0.0497 (9)	0.0620 (9)	−0.0322 (7)	−0.0040 (7)	0.0026 (7)
O1	0.0325 (6)	0.0237 (6)	0.0290 (6)	−0.0070 (5)	−0.0088 (5)	−0.0090 (5)
O2	0.0296 (6)	0.0290 (7)	0.0250 (6)	−0.0048 (5)	−0.0041 (5)	−0.0089 (5)
O3	0.0325 (6)	0.0346 (7)	0.0306 (6)	−0.0073 (6)	−0.0154 (5)	−0.0061 (6)
C1	0.0276 (8)	0.0232 (8)	0.0228 (7)	−0.0067 (7)	−0.0077 (6)	−0.0049 (7)
C2	0.0230 (7)	0.0222 (8)	0.0226 (7)	−0.0064 (6)	−0.0058 (6)	−0.0041 (6)
C3	0.0285 (8)	0.0234 (9)	0.0237 (8)	−0.0065 (7)	−0.0063 (6)	−0.0059 (7)
C4	0.0319 (8)	0.0303 (9)	0.0201 (7)	−0.0097 (7)	−0.0074 (6)	−0.0045 (7)
C5	0.0305 (8)	0.0260 (9)	0.0265 (8)	−0.0090 (7)	−0.0089 (7)	0.0009 (7)
C6	0.0271 (8)	0.0224 (9)	0.0294 (8)	−0.0091 (7)	−0.0058 (7)	−0.0020 (7)
C7	0.0262 (8)	0.0226 (9)	0.0253 (8)	−0.0075 (7)	−0.0055 (6)	−0.0061 (7)
C8	0.0277 (8)	0.0264 (9)	0.0267 (8)	−0.0077 (7)	−0.0062 (6)	−0.0075 (7)
C9	0.0357 (9)	0.0217 (9)	0.0397 (10)	−0.0056 (8)	−0.0106 (8)	−0.0047 (8)
C10	0.0431 (10)	0.0364 (11)	0.0302 (9)	−0.0093 (9)	−0.0125 (8)	−0.0132 (8)
C11	0.0267 (8)	0.0208 (8)	0.0235 (8)	−0.0034 (7)	−0.0072 (6)	−0.0041 (7)
C12	0.0360 (9)	0.0344 (10)	0.0253 (8)	−0.0077 (8)	−0.0113 (7)	−0.0041 (8)
C13	0.0435 (11)	0.0415 (12)	0.0254 (9)	−0.0122 (9)	−0.0071 (8)	0.0027 (8)
C14	0.0367 (10)	0.0264 (10)	0.0437 (11)	−0.0116 (8)	−0.0042 (8)	−0.0013 (9)
C15	0.0387 (10)	0.0345 (11)	0.0445 (11)	−0.0135 (9)	−0.0100 (8)	−0.0135 (9)
C16	0.0343 (9)	0.0305 (10)	0.0268 (8)	−0.0077 (8)	−0.0078 (7)	−0.0089 (8)

Geometric parameters (Å, º) top

Br1—C4	1.9019 (16)	C6—C9	1.498 (3)
S1—O2	1.4396 (12)	C8—C10	1.480 (2)
S1—O3	1.4403 (12)	C9—H9A	0.9800
S1—C1	1.7354 (18)	C9—H9B	0.9800
S1—C11	1.7612 (17)	C9—H9C	0.9800
F1—C14	1.354 (2)	C10—H10A	0.9800
O1—C8	1.368 (2)	C10—H10B	0.9800
O1—C7	1.377 (2)	C10—H10C	0.9800
C1—C8	1.362 (2)	C11—C12	1.387 (2)
C1—C2	1.448 (2)	C11—C16	1.391 (2)
C2—C7	1.395 (2)	C12—C13	1.379 (3)
C2—C3	1.398 (2)	C12—H12	0.9500
C3—C4	1.382 (3)	C13—C14	1.371 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.392 (3)	C14—C15	1.371 (3)
C5—C6	1.389 (2)	C15—C16	1.385 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.383 (2)	C16—H16	0.9500

O2—S1—O3	119.77 (8)	C6—C9—H9A	109.5
O2—S1—C1	106.57 (8)	C6—C9—H9B	109.5
O3—S1—C1	108.82 (8)	H9A—C9—H9B	109.5
O2—S1—C11	107.04 (8)	C6—C9—H9C	109.5
O3—S1—C11	107.58 (8)	H9A—C9—H9C	109.5
C1—S1—C11	106.33 (8)	H9B—C9—H9C	109.5
C8—O1—C7	107.04 (13)	C8—C10—H10A	109.5
C8—C1—C2	107.36 (15)	C8—C10—H10B	109.5
C8—C1—S1	126.67 (13)	H10A—C10—H10B	109.5
C2—C1—S1	125.96 (13)	C8—C10—H10C	109.5
C7—C2—C3	119.41 (15)	H10A—C10—H10C	109.5
C7—C2—C1	104.63 (14)	H10B—C10—H10C	109.5
C3—C2—C1	135.96 (16)	C12—C11—C16	121.12 (16)
C4—C3—C2	115.86 (16)	C12—C11—S1	119.34 (13)
C4—C3—H3	122.1	C16—C11—S1	119.49 (13)
C2—C3—H3	122.1	C13—C12—C11	119.55 (17)
C3—C4—C5	123.81 (16)	C13—C12—H12	120.2
C3—C4—Br1	118.15 (14)	C11—C12—H12	120.2
C5—C4—Br1	118.04 (13)	C14—C13—C12	118.25 (18)
C6—C5—C4	121.09 (17)	C14—C13—H13	120.9
C6—C5—H5	119.5	C12—C13—H13	120.9
C4—C5—H5	119.5	F1—C14—C13	118.26 (19)
C7—C6—C5	114.69 (16)	F1—C14—C15	118.05 (19)
C7—C6—C9	122.24 (16)	C13—C14—C15	123.68 (18)
C5—C6—C9	123.06 (17)	C14—C15—C16	118.15 (18)
O1—C7—C6	124.43 (16)	C14—C15—H15	120.9
O1—C7—C2	110.43 (14)	C16—C15—H15	120.9
C6—C7—C2	125.14 (15)	C15—C16—C11	119.24 (17)
C1—C8—O1	110.54 (15)	C15—C16—H16	120.4
C1—C8—C10	134.51 (18)	C11—C16—H16	120.4
O1—C8—C10	114.95 (15)

O2—S1—C1—C8	157.48 (15)	C1—C2—C7—O1	−0.36 (18)
O3—S1—C1—C8	27.03 (18)	C3—C2—C7—C6	−1.2 (3)
C11—S1—C1—C8	−88.59 (17)	C1—C2—C7—C6	178.73 (16)
O2—S1—C1—C2	−22.76 (17)	C2—C1—C8—O1	0.24 (19)
O3—S1—C1—C2	−153.21 (14)	S1—C1—C8—O1	−179.96 (12)
C11—S1—C1—C2	91.18 (15)	C2—C1—C8—C10	−179.02 (19)
C8—C1—C2—C7	0.08 (18)	S1—C1—C8—C10	0.8 (3)
S1—C1—C2—C7	−179.73 (13)	C7—O1—C8—C1	−0.46 (19)
C8—C1—C2—C3	179.94 (19)	C7—O1—C8—C10	178.96 (15)
S1—C1—C2—C3	0.1 (3)	O2—S1—C11—C12	−147.79 (15)
C7—C2—C3—C4	0.8 (2)	O3—S1—C11—C12	−17.86 (17)
C1—C2—C3—C4	−179.07 (18)	C1—S1—C11—C12	98.59 (16)
C2—C3—C4—C5	0.1 (3)	O2—S1—C11—C16	29.83 (17)
C2—C3—C4—Br1	179.36 (12)	O3—S1—C11—C16	159.77 (14)
C3—C4—C5—C6	−0.8 (3)	C1—S1—C11—C16	−83.78 (16)
Br1—C4—C5—C6	179.98 (13)	C16—C11—C12—C13	−0.6 (3)
C4—C5—C6—C7	0.5 (2)	S1—C11—C12—C13	176.99 (16)
C4—C5—C6—C9	−179.85 (16)	C11—C12—C13—C14	0.8 (3)
C8—O1—C7—C6	−178.59 (16)	C12—C13—C14—F1	179.41 (19)
C8—O1—C7—C2	0.51 (18)	C12—C13—C14—C15	0.1 (3)
C5—C6—C7—O1	179.48 (15)	F1—C14—C15—C16	179.55 (18)
C9—C6—C7—O1	−0.2 (3)	C13—C14—C15—C16	−1.1 (3)
C5—C6—C7—C2	0.5 (2)	C14—C15—C16—C11	1.3 (3)
C9—C6—C7—C2	−179.19 (16)	C12—C11—C16—C15	−0.5 (3)
C3—C2—C7—O1	179.75 (14)	S1—C11—C16—C15	−178.04 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.95	2.53	3.408 (2)	154
C9—H9A···O2ⁱⁱ	0.98	2.50	3.304 (2)	139

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂BrFO₃S
M_r	383.23
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.0789 (1), 9.2754 (2), 11.3555 (2)
α, β, γ (°)	71.283 (1), 72.645 (1), 70.042 (1)
V (Å³)	740.30 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.94
Crystal size (mm)	0.29 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.527, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14090, 3680, 3259
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.02
No. of reflections	3680
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.47

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
C3—H3···O2ⁱ	0.95	2.53	3.408 (2)	154
C9—H9A···O2ⁱⁱ	0.98	2.50	3.304 (2)	139

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

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

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
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