5-Bromo-3-cyclo­hexyl­sulfonyl-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S160053681101539X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1279

doi:10.1107/S160053681101539X

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5-Bromo-3-cyclohexylsulfonyl-2,7-dimethyl-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 14 April 2011; accepted 24 April 2011; online 29 April 2011)

In the title compound, C₁₆H₁₉BrO₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak C—H⋯O hydrogen bonds and Br⋯O contacts [3.211 (1) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₉BrO₃S
M_r = 371.28
Triclinic, $[P \overline 1]$
a = 6.6992 (2) Å
b = 8.4654 (2) Å
c = 14.1065 (3) Å
α = 101.773 (1)°
β = 99.283 (1)°
γ = 92.067 (1)°
V = 770.94 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.81 mm⁻¹
T = 173 K
0.26 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.525, T_max = 0.591
13840 measured reflections
3542 independent reflections
3247 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.066
S = 1.10
3542 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2ⁱ	0.98	2.55	3.384 (2)	143
Symmetry code: (i) x+1, y, z.

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/S160053681101539X/lr2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101539X/lr2008Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681101539X/lr2008Isup3.cml

checkCIF report

Comment top

Many compounds containing a benzofuran skeleton have drawn much attention owing to diverse pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2011a,b), 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 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a methyl H atom and the O atom of the sulfonyl group (Table 1; C10—H10B···O2ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by a Br···O halogen-bonding between the bromine and the O atom of the sulfonyl group [Br1···O2ⁱ = 3.211 (1) Å, C4—Br1···O2ⁱ = 168.13 (6)°] (Politzer et al., 2007).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-cyclohexylsulfanyl-2,7-dimethyl-1-benzofuran (305 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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 72%, m.p. 440–441 K; R_f = 0.55 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone 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. Displacement ellipsoids are drawn at the 50% probability level.H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the Br···O and C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x, - y + 1, - z + 1; (ii) x + 1, y, z; (iii) x - 1, y, z.]

5-Bromo-3-cyclohexylsulfonyl-2,7-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₉BrO₃S	Z = 2
M_r = 371.28	F(000) = 380
Triclinic, P1	D_x = 1.599 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6992 (2) Å	Cell parameters from 7893 reflections
b = 8.4654 (2) Å	θ = 2.5–27.5°
c = 14.1065 (3) Å	µ = 2.81 mm⁻¹
α = 101.773 (1)°	T = 173 K
β = 99.283 (1)°	Block, colourless
γ = 92.067 (1)°	0.26 × 0.25 × 0.21 mm
V = 770.94 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3542 independent reflections
Radiation source: rotating anode	3247 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.5°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→11
T_min = 0.525, T_max = 0.591	l = −18→18
13840 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: difference Fourier map
wR(F²) = 0.066	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0331P)² + 0.2732P] where P = (F_o² + 2F_c²)/3
3542 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₆H₁₉BrO₃S	γ = 92.067 (1)°
M_r = 371.28	V = 770.94 (3) Å³
Triclinic, P1	Z = 2
a = 6.6992 (2) Å	Mo Kα radiation
b = 8.4654 (2) Å	µ = 2.81 mm⁻¹
c = 14.1065 (3) Å	T = 173 K
α = 101.773 (1)°	0.26 × 0.25 × 0.21 mm
β = 99.283 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3542 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3247 reflections with I > 2σ(I)
T_min = 0.525, T_max = 0.591	R_int = 0.032
13840 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.10	Δρ_max = 0.27 e Å⁻³
3542 reflections	Δρ_min = −0.59 e Å⁻³
192 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	0.23387 (3)	0.56750 (2)	0.639762 (13)	0.02642 (7)
S1	0.18306 (6)	0.68046 (5)	0.21799 (3)	0.02179 (10)
O1	0.68271 (17)	0.88970 (14)	0.39103 (9)	0.0209 (2)
O2	0.00575 (19)	0.67623 (17)	0.26350 (10)	0.0308 (3)
O3	0.1772 (2)	0.76300 (17)	0.13792 (10)	0.0319 (3)
C1	0.3856 (3)	0.7638 (2)	0.31083 (12)	0.0199 (3)
C2	0.4083 (2)	0.7416 (2)	0.41070 (12)	0.0186 (3)
C3	0.2943 (2)	0.6642 (2)	0.46471 (12)	0.0205 (3)
H3	0.1661	0.6086	0.4362	0.025*
C4	0.3779 (3)	0.6731 (2)	0.56194 (13)	0.0205 (3)
C5	0.5655 (3)	0.7538 (2)	0.60597 (12)	0.0207 (3)
H5	0.6147	0.7562	0.6733	0.025*
C6	0.6817 (2)	0.8306 (2)	0.55345 (12)	0.0193 (3)
C7	0.5946 (2)	0.8214 (2)	0.45637 (12)	0.0187 (3)
C8	0.5527 (3)	0.8528 (2)	0.30300 (12)	0.0210 (3)
C9	0.8873 (3)	0.9137 (2)	0.59697 (14)	0.0259 (4)
H9A	0.9904	0.8546	0.5652	0.039*
H9B	0.9150	0.9161	0.6676	0.039*
H9C	0.8910	1.0246	0.5865	0.039*
C10	0.6222 (3)	0.9166 (2)	0.22308 (13)	0.0278 (4)
H10A	0.5172	0.8903	0.1641	0.042*
H10B	0.7471	0.8677	0.2085	0.042*
H10C	0.6483	1.0343	0.2435	0.042*
C11	0.2440 (3)	0.4760 (2)	0.17876 (12)	0.0212 (3)
H11	0.2926	0.4334	0.2389	0.025*
C12	0.0529 (3)	0.3725 (2)	0.12283 (14)	0.0305 (4)
H12A	−0.0521	0.3788	0.1652	0.037*
H12B	−0.0016	0.4137	0.0637	0.037*
C13	0.1038 (3)	0.1970 (3)	0.09238 (17)	0.0399 (5)
H13A	0.1455	0.1532	0.1519	0.048*
H13B	−0.0187	0.1316	0.0534	0.048*
C14	0.2727 (3)	0.1828 (3)	0.03208 (16)	0.0386 (5)
H14A	0.2253	0.2152	−0.0309	0.046*
H14B	0.3069	0.0686	0.0169	0.046*
C15	0.4616 (3)	0.2888 (2)	0.08642 (15)	0.0321 (4)
H15A	0.5648	0.2825	0.0431	0.039*
H15B	0.5189	0.2477	0.1452	0.039*
C16	0.4139 (3)	0.4651 (2)	0.11810 (14)	0.0277 (4)
H16A	0.5368	0.5293	0.1576	0.033*
H16B	0.3723	0.5107	0.0592	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02483 (10)	0.02977 (12)	0.02630 (10)	−0.00189 (7)	0.00582 (7)	0.00932 (8)
S1	0.0202 (2)	0.0225 (2)	0.0199 (2)	0.00190 (16)	−0.00183 (15)	0.00234 (17)
O1	0.0188 (6)	0.0227 (6)	0.0203 (6)	−0.0014 (5)	0.0035 (5)	0.0031 (5)
O2	0.0196 (6)	0.0361 (8)	0.0324 (7)	0.0021 (5)	0.0016 (5)	−0.0002 (6)
O3	0.0372 (8)	0.0301 (7)	0.0265 (7)	0.0024 (6)	−0.0058 (6)	0.0103 (6)
C1	0.0199 (8)	0.0190 (8)	0.0187 (8)	0.0020 (6)	0.0012 (6)	0.0007 (6)
C2	0.0190 (8)	0.0149 (8)	0.0196 (8)	0.0025 (6)	0.0017 (6)	−0.0005 (6)
C3	0.0177 (8)	0.0186 (8)	0.0228 (8)	−0.0010 (6)	0.0024 (6)	0.0004 (7)
C4	0.0205 (8)	0.0177 (8)	0.0235 (8)	0.0008 (6)	0.0056 (6)	0.0038 (7)
C5	0.0216 (8)	0.0196 (8)	0.0193 (8)	0.0035 (6)	0.0008 (6)	0.0019 (7)
C6	0.0169 (7)	0.0169 (8)	0.0216 (8)	0.0016 (6)	0.0012 (6)	−0.0003 (6)
C7	0.0187 (8)	0.0164 (8)	0.0209 (8)	0.0016 (6)	0.0051 (6)	0.0024 (6)
C8	0.0231 (8)	0.0189 (8)	0.0191 (8)	0.0044 (6)	0.0020 (6)	0.0003 (7)
C9	0.0190 (8)	0.0286 (10)	0.0270 (9)	−0.0014 (7)	−0.0007 (7)	0.0027 (8)
C10	0.0284 (9)	0.0320 (10)	0.0245 (9)	0.0009 (8)	0.0060 (7)	0.0085 (8)
C11	0.0235 (8)	0.0198 (8)	0.0176 (8)	−0.0012 (7)	0.0003 (6)	0.0010 (7)
C12	0.0256 (9)	0.0335 (11)	0.0267 (9)	−0.0072 (8)	0.0036 (7)	−0.0043 (8)
C13	0.0410 (12)	0.0302 (11)	0.0400 (12)	−0.0125 (9)	0.0069 (9)	−0.0095 (9)
C14	0.0407 (12)	0.0329 (11)	0.0334 (11)	0.0007 (9)	0.0038 (9)	−0.0107 (9)
C15	0.0304 (10)	0.0286 (10)	0.0339 (10)	0.0035 (8)	0.0047 (8)	−0.0008 (8)
C16	0.0258 (9)	0.0266 (10)	0.0300 (9)	0.0005 (7)	0.0068 (7)	0.0032 (8)

Geometric parameters (Å, º) top

Br1—C4	1.9011 (17)	C9—H9C	0.9800
Br1—O2ⁱ	3.2114 (14)	C10—H10A	0.9800
S1—O3	1.4406 (13)	C10—H10B	0.9800
S1—O2	1.4410 (14)	C10—H10C	0.9800
S1—C1	1.7420 (17)	C11—C16	1.525 (3)
S1—C11	1.7891 (18)	C11—C12	1.530 (2)
O1—C8	1.368 (2)	C11—H11	1.0000
O1—C7	1.379 (2)	C12—C13	1.526 (3)
C1—C8	1.359 (2)	C12—H12A	0.9900
C1—C2	1.444 (2)	C12—H12B	0.9900
C2—C7	1.390 (2)	C13—C14	1.515 (3)
C2—C3	1.396 (2)	C13—H13A	0.9900
C3—C4	1.381 (2)	C13—H13B	0.9900
C3—H3	0.9500	C14—C15	1.523 (3)
C4—C5	1.395 (2)	C14—H14A	0.9900
C5—C6	1.387 (2)	C14—H14B	0.9900
C5—H5	0.9500	C15—C16	1.529 (3)
C6—C7	1.385 (2)	C15—H15A	0.9900
C6—C9	1.500 (2)	C15—H15B	0.9900
C8—C10	1.476 (2)	C16—H16A	0.9900
C9—H9A	0.9800	C16—H16B	0.9900
C9—H9B	0.9800

C4—Br1—O2ⁱ	168.13 (6)	H10A—C10—H10B	109.5
O3—S1—O2	118.36 (9)	C8—C10—H10C	109.5
O3—S1—C1	109.59 (8)	H10A—C10—H10C	109.5
O2—S1—C1	107.06 (8)	H10B—C10—H10C	109.5
O3—S1—C11	109.54 (8)	C16—C11—C12	111.87 (15)
O2—S1—C11	107.55 (8)	C16—C11—S1	111.84 (12)
C1—S1—C11	103.73 (8)	C12—C11—S1	109.74 (13)
C8—O1—C7	107.00 (13)	C16—C11—H11	107.7
C8—C1—C2	107.69 (15)	C12—C11—H11	107.7
C8—C1—S1	127.55 (14)	S1—C11—H11	107.7
C2—C1—S1	124.69 (13)	C13—C12—C11	109.64 (16)
C7—C2—C3	119.34 (15)	C13—C12—H12A	109.7
C7—C2—C1	104.60 (15)	C11—C12—H12A	109.7
C3—C2—C1	136.06 (15)	C13—C12—H12B	109.7
C4—C3—C2	116.33 (15)	C11—C12—H12B	109.7
C4—C3—H3	121.8	H12A—C12—H12B	108.2
C2—C3—H3	121.8	C14—C13—C12	111.54 (18)
C3—C4—C5	123.20 (16)	C14—C13—H13A	109.3
C3—C4—Br1	118.84 (12)	C12—C13—H13A	109.3
C5—C4—Br1	117.95 (13)	C14—C13—H13B	109.3
C6—C5—C4	121.37 (15)	C12—C13—H13B	109.3
C6—C5—H5	119.3	H13A—C13—H13B	108.0
C4—C5—H5	119.3	C13—C14—C15	111.59 (17)
C7—C6—C5	114.55 (15)	C13—C14—H14A	109.3
C7—C6—C9	122.37 (16)	C15—C14—H14A	109.3
C5—C6—C9	123.07 (16)	C13—C14—H14B	109.3
O1—C7—C6	124.35 (15)	C15—C14—H14B	109.3
O1—C7—C2	110.43 (14)	H14A—C14—H14B	108.0
C6—C7—C2	125.21 (15)	C14—C15—C16	111.47 (17)
C1—C8—O1	110.27 (15)	C14—C15—H15A	109.3
C1—C8—C10	134.88 (16)	C16—C15—H15A	109.3
O1—C8—C10	114.85 (15)	C14—C15—H15B	109.3
C6—C9—H9A	109.5	C16—C15—H15B	109.3
C6—C9—H9B	109.5	H15A—C15—H15B	108.0
H9A—C9—H9B	109.5	C11—C16—C15	110.14 (16)
C6—C9—H9C	109.5	C11—C16—H16A	109.6
H9A—C9—H9C	109.5	C15—C16—H16A	109.6
H9B—C9—H9C	109.5	C11—C16—H16B	109.6
C8—C10—H10A	109.5	C15—C16—H16B	109.6
C8—C10—H10B	109.5	H16A—C16—H16B	108.1

O3—S1—C1—C8	−20.06 (19)	C9—C6—C7—C2	177.58 (17)
O2—S1—C1—C8	−149.60 (16)	C3—C2—C7—O1	−179.90 (14)
C11—S1—C1—C8	96.84 (17)	C1—C2—C7—O1	0.31 (18)
O3—S1—C1—C2	163.32 (14)	C3—C2—C7—C6	0.7 (3)
O2—S1—C1—C2	33.78 (17)	C1—C2—C7—C6	−179.11 (16)
C11—S1—C1—C2	−79.78 (16)	C2—C1—C8—O1	0.13 (19)
C8—C1—C2—C7	−0.26 (19)	S1—C1—C8—O1	−176.95 (12)
S1—C1—C2—C7	176.92 (13)	C2—C1—C8—C10	−179.71 (19)
C8—C1—C2—C3	179.99 (19)	S1—C1—C8—C10	3.2 (3)
S1—C1—C2—C3	−2.8 (3)	C7—O1—C8—C1	0.06 (18)
C7—C2—C3—C4	−0.2 (2)	C7—O1—C8—C10	179.94 (15)
C1—C2—C3—C4	179.56 (18)	O3—S1—C11—C16	43.02 (15)
C2—C3—C4—C5	0.0 (3)	O2—S1—C11—C16	172.87 (12)
C2—C3—C4—Br1	−178.90 (12)	C1—S1—C11—C16	−73.92 (14)
O2ⁱ—Br1—C4—C3	56.5 (3)	O3—S1—C11—C12	−81.75 (14)
O2ⁱ—Br1—C4—C5	−122.5 (3)	O2—S1—C11—C12	48.11 (14)
C3—C4—C5—C6	−0.4 (3)	C1—S1—C11—C12	161.32 (13)
Br1—C4—C5—C6	178.57 (13)	C16—C11—C12—C13	57.1 (2)
C4—C5—C6—C7	0.8 (2)	S1—C11—C12—C13	−178.14 (14)
C4—C5—C6—C9	−177.76 (17)	C11—C12—C13—C14	−56.2 (2)
C8—O1—C7—C6	179.18 (16)	C12—C13—C14—C15	55.8 (2)
C8—O1—C7—C2	−0.24 (18)	C13—C14—C15—C16	−55.0 (3)
C5—C6—C7—O1	179.69 (15)	C12—C11—C16—C15	−56.6 (2)
C9—C6—C7—O1	−1.8 (3)	S1—C11—C16—C15	179.81 (12)
C5—C6—C7—C2	−1.0 (3)	C14—C15—C16—C11	54.9 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱⁱ	0.98	2.55	3.384 (2)	143

Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉BrO₃S
M_r	371.28
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.6992 (2), 8.4654 (2), 14.1065 (3)
α, β, γ (°)	101.773 (1), 99.283 (1), 92.067 (1)
V (Å³)	770.94 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.81
Crystal size (mm)	0.26 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.525, 0.591
No. of measured, independent and observed [I > 2σ(I)] reflections	13840, 3542, 3247
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.066, 1.10
No. of reflections	3542
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.59

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
C10—H10B···O2ⁱ	0.98	2.55	3.384 (2)	143

Symmetry code: (i) x+1, y, z.

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
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
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o542. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o828. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS 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. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 5| May 2011| Page o1279

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