5-Ethyl-3-(4-Fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536810036391

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2575

doi:10.1107/S1600536810036391

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5-Ethyl-3-(4-Fluorophenylsulfonyl)-2-methyl-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 9 September 2010; accepted 11 September 2010; online 18 September 2010)

In the title molecule, C₁₇H₁₅FO₃S, the 4-fluorophenyl ring makes a dihedral angle of 74.06 (4)° with the mean plane of the benzofuran fragment. In the crystal structure, molecules are linked by weak intermolecular C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits aromatic π–π interactions between the benzene rings of adjacent molecules [centroid–centroid distance = 3.629 (2) Å].

Related literature

For the crystal structures of similar 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ,b ). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ).

Experimental

Crystal data

C₁₇H₁₅FO₃S
M_r = 318.35
Triclinic, $[P \overline 1]$
a = 8.0042 (1) Å
b = 9.7114 (2) Å
c = 11.3741 (2) Å
α = 66.487 (1)°
β = 82.998 (1)°
γ = 67.964 (1)°
V = 751.10 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.31 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.929, T_max = 0.946
13998 measured reflections
3722 independent reflections
3264 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.04
3722 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.40	3.3143 (17)	161
C11—H11C⋯Cgⁱⁱ	0.98	2.66	3.491 (2)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -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/S1600536810036391/su2211sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036391/su2211Isup2.hkl

checkCIF report

Comment top

Many compounds containing a benzofuran ring show important biological properties such as, antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) activities. These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As part of our ongoing studies of the effect of side chain substituents on the solid state structures of 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1) the benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring makes a dihedral angle of 74.06 (4)° with the mean plane of the benzofuran fragment.

The crystal packing (Fig. 2) is stabilized by a weak intermolecular C–H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the O═ S═O unit[ C13–H13···O2ⁱ; see Table 1], and by an intermolecular C–H···π interaction between a methyl H-atom and the benzene ring of a neighbouring molecule [C11–H11C···Cgⁱⁱ ; see Table 1]. The molecular packing (Fig. 2) is further stabilized by an aromatic π···π interaction between the benzene rings of neighbouring molecules, with a Cg···Cgⁱⁱⁱ distance of 3.629 (2) Å (Cg is the centroid of the C2-C7 benzene ring; see Table 1).

Related literature top

For the crystal structures of similar 3-(4-fluorophenylsulfony)l-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003).

Experimental top

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-ethyl-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (229 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 (silica gel, benzene) to afford the title compound as a colorless solid [yield 82%, m.p. 377-378 K; R_f = 0.68 (benzene)]. Single crystals, suitable for X-ray diffraction, were prepared by slow evaporation of a solution of the title compound in diisopropyl ether 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 molecule with the atom numbering scheme. 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 C–H···O, C–H..π and π···π interactions (dotted lines) in the crystal structure of the title compound. [Cg denotes the centroid of benzene ring C2-C7; Symmetry codes: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 2, - z + 1; (iii) - x, - y + 2, - z + 1; (iv) x - 1, y, z.]

5-Ethyl-3-(4-Fluorophenylsulfonyl)-2-methyl-1-benzofuran top

Crystal data top

C₁₇H₁₅FO₃S	Z = 2
M_r = 318.35	F(000) = 332
Triclinic, P1	D_x = 1.408 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0042 (1) Å	Cell parameters from 6492 reflections
b = 9.7114 (2) Å	θ = 2.5–28.2°
c = 11.3741 (2) Å	µ = 0.24 mm⁻¹
α = 66.487 (1)°	T = 173 K
β = 82.998 (1)°	Block, colourless
γ = 67.964 (1)°	0.31 × 0.25 × 0.24 mm
V = 751.10 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3722 independent reflections
Radiation source: rotating anode	3264 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.929, T_max = 0.946	l = −15→15
13998 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: difference Fourier map
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0517P)² + 0.2601P] where P = (F_o² + 2F_c²)/3
3722 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₇H₁₅FO₃S	γ = 67.964 (1)°
M_r = 318.35	V = 751.10 (2) Å³
Triclinic, P1	Z = 2
a = 8.0042 (1) Å	Mo Kα radiation
b = 9.7114 (2) Å	µ = 0.24 mm⁻¹
c = 11.3741 (2) Å	T = 173 K
α = 66.487 (1)°	0.31 × 0.25 × 0.24 mm
β = 82.998 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3722 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3264 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.946	R_int = 0.027
13998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
3722 reflections	Δρ_min = −0.38 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
S1	0.53064 (4)	0.61417 (4)	0.69284 (3)	0.02667 (10)
F1	0.02306 (15)	0.28696 (12)	0.93170 (10)	0.0495 (3)
O1	0.26044 (14)	1.07835 (12)	0.57702 (10)	0.0326 (2)
O2	0.61844 (14)	0.55702 (13)	0.59437 (10)	0.0352 (2)
O3	0.63741 (14)	0.59481 (13)	0.79503 (10)	0.0354 (2)
C1	0.39955 (18)	0.81537 (16)	0.61842 (12)	0.0255 (3)
C2	0.29794 (17)	0.88735 (16)	0.49822 (12)	0.0261 (3)
C3	0.26704 (18)	0.83239 (17)	0.40981 (13)	0.0290 (3)
H3	0.3221	0.7221	0.4220	0.035*
C4	0.15386 (19)	0.94248 (19)	0.30318 (13)	0.0331 (3)
C5	0.0762 (2)	1.10491 (19)	0.28633 (15)	0.0381 (3)
H5	0.0007	1.1788	0.2126	0.046*
C6	0.1050 (2)	1.16199 (18)	0.37250 (15)	0.0371 (3)
H6	0.0517	1.2724	0.3600	0.045*
C7	0.21583 (18)	1.04904 (17)	0.47799 (13)	0.0295 (3)
C8	0.37157 (18)	0.93495 (17)	0.66117 (13)	0.0285 (3)
C9	0.1224 (2)	0.8853 (2)	0.20518 (15)	0.0438 (4)
H9A	0.0020	0.9550	0.1632	0.053*
H9B	0.1225	0.7745	0.2496	0.053*
C10	0.2631 (2)	0.8871 (2)	0.10352 (16)	0.0450 (4)
H10A	0.2596	0.9975	0.0562	0.067*
H10B	0.2381	0.8462	0.0441	0.067*
H10C	0.3828	0.8187	0.1444	0.067*
C11	0.4355 (2)	0.9415 (2)	0.77493 (15)	0.0372 (3)
H11A	0.4909	0.8320	0.8383	0.056*
H11B	0.3331	1.0027	0.8127	0.056*
H11C	0.5246	0.9942	0.7491	0.056*
C12	0.37463 (18)	0.51746 (15)	0.76302 (12)	0.0267 (3)
C13	0.3061 (2)	0.45940 (16)	0.69364 (13)	0.0314 (3)
H13	0.3415	0.4729	0.6081	0.038*
C14	0.1857 (2)	0.38180 (17)	0.75030 (15)	0.0358 (3)
H14	0.1357	0.3425	0.7044	0.043*
C15	0.1402 (2)	0.36313 (17)	0.87531 (15)	0.0350 (3)
C16	0.2084 (2)	0.41710 (18)	0.94653 (14)	0.0344 (3)
H16	0.1758	0.3997	1.0330	0.041*
C17	0.32586 (19)	0.49745 (17)	0.88873 (13)	0.0302 (3)
H17	0.3729	0.5387	0.9346	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02624 (17)	0.02837 (17)	0.02451 (17)	−0.00613 (13)	−0.00164 (12)	−0.01197 (13)
F1	0.0537 (6)	0.0503 (6)	0.0491 (6)	−0.0316 (5)	0.0016 (5)	−0.0115 (5)
O1	0.0343 (5)	0.0282 (5)	0.0366 (5)	−0.0118 (4)	0.0075 (4)	−0.0151 (4)
O2	0.0347 (5)	0.0364 (5)	0.0325 (5)	−0.0060 (4)	0.0044 (4)	−0.0186 (4)
O3	0.0327 (5)	0.0419 (6)	0.0319 (5)	−0.0118 (4)	−0.0074 (4)	−0.0135 (4)
C1	0.0258 (6)	0.0270 (6)	0.0248 (6)	−0.0096 (5)	0.0020 (5)	−0.0112 (5)
C2	0.0233 (6)	0.0285 (6)	0.0239 (6)	−0.0093 (5)	0.0032 (5)	−0.0082 (5)
C3	0.0272 (6)	0.0331 (7)	0.0258 (6)	−0.0113 (5)	0.0014 (5)	−0.0101 (5)
C4	0.0253 (6)	0.0458 (8)	0.0250 (6)	−0.0145 (6)	0.0023 (5)	−0.0093 (6)
C5	0.0264 (7)	0.0427 (8)	0.0291 (7)	−0.0079 (6)	0.0000 (5)	−0.0020 (6)
C6	0.0296 (7)	0.0283 (7)	0.0391 (8)	−0.0049 (6)	0.0051 (6)	−0.0050 (6)
C7	0.0270 (6)	0.0294 (7)	0.0300 (7)	−0.0111 (5)	0.0064 (5)	−0.0101 (5)
C8	0.0270 (6)	0.0324 (7)	0.0300 (7)	−0.0134 (5)	0.0074 (5)	−0.0151 (5)
C9	0.0389 (8)	0.0638 (11)	0.0297 (8)	−0.0213 (8)	−0.0046 (6)	−0.0146 (7)
C10	0.0487 (9)	0.0479 (9)	0.0336 (8)	−0.0118 (8)	0.0014 (7)	−0.0161 (7)
C11	0.0411 (8)	0.0454 (8)	0.0375 (8)	−0.0199 (7)	0.0083 (6)	−0.0262 (7)
C12	0.0279 (6)	0.0235 (6)	0.0256 (6)	−0.0050 (5)	−0.0036 (5)	−0.0092 (5)
C13	0.0392 (8)	0.0273 (6)	0.0268 (6)	−0.0077 (6)	−0.0049 (6)	−0.0116 (5)
C14	0.0448 (8)	0.0291 (7)	0.0369 (8)	−0.0136 (6)	−0.0068 (6)	−0.0135 (6)
C15	0.0349 (7)	0.0283 (7)	0.0375 (8)	−0.0113 (6)	−0.0043 (6)	−0.0067 (6)
C16	0.0341 (7)	0.0367 (7)	0.0274 (7)	−0.0094 (6)	−0.0014 (6)	−0.0098 (6)
C17	0.0314 (7)	0.0326 (7)	0.0264 (6)	−0.0080 (5)	−0.0042 (5)	−0.0128 (5)

Geometric parameters (Å, º) top

S1—O3	1.4366 (10)	C9—C10	1.512 (2)
S1—O2	1.4380 (10)	C9—H9A	0.9900
S1—C1	1.7302 (13)	C9—H9B	0.9900
S1—C12	1.7656 (14)	C10—H10A	0.9800
F1—C15	1.3542 (17)	C10—H10B	0.9800
O1—C8	1.3642 (17)	C10—H10C	0.9800
O1—C7	1.3811 (17)	C11—H11A	0.9800
C1—C8	1.3652 (18)	C11—H11B	0.9800
C1—C2	1.4496 (18)	C11—H11C	0.9800
C2—C7	1.3874 (19)	C12—C17	1.3905 (19)
C2—C3	1.3947 (19)	C12—C13	1.3909 (19)
C3—C4	1.3932 (19)	C13—C14	1.385 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.401 (2)	C14—C15	1.380 (2)
C4—C9	1.510 (2)	C14—H14	0.9500
C5—C6	1.380 (2)	C15—C16	1.375 (2)
C5—H5	0.9500	C16—C17	1.384 (2)
C6—C7	1.382 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.4802 (19)

O3—S1—O2	119.42 (6)	C4—C9—H9B	109.0
O3—S1—C1	109.13 (6)	C10—C9—H9B	109.0
O2—S1—C1	107.67 (6)	H9A—C9—H9B	107.8
O3—S1—C12	107.56 (6)	C9—C10—H10A	109.5
O2—S1—C12	107.33 (6)	C9—C10—H10B	109.5
C1—S1—C12	104.80 (6)	H10A—C10—H10B	109.5
C8—O1—C7	107.11 (10)	C9—C10—H10C	109.5
C8—C1—C2	107.43 (12)	H10A—C10—H10C	109.5
C8—C1—S1	126.92 (11)	H10B—C10—H10C	109.5
C2—C1—S1	125.65 (10)	C8—C11—H11A	109.5
C7—C2—C3	119.46 (13)	C8—C11—H11B	109.5
C7—C2—C1	104.60 (12)	H11A—C11—H11B	109.5
C3—C2—C1	135.93 (13)	C8—C11—H11C	109.5
C4—C3—C2	118.67 (13)	H11A—C11—H11C	109.5
C4—C3—H3	120.7	H11B—C11—H11C	109.5
C2—C3—H3	120.7	C17—C12—C13	121.14 (14)
C3—C4—C5	119.60 (14)	C17—C12—S1	118.90 (11)
C3—C4—C9	119.24 (15)	C13—C12—S1	119.93 (11)
C5—C4—C9	121.12 (14)	C14—C13—C12	119.42 (13)
C6—C5—C4	122.72 (14)	C14—C13—H13	120.3
C6—C5—H5	118.6	C12—C13—H13	120.3
C4—C5—H5	118.6	C15—C14—C13	118.15 (13)
C5—C6—C7	116.07 (14)	C15—C14—H14	120.9
C5—C6—H6	122.0	C13—C14—H14	120.9
C7—C6—H6	122.0	F1—C15—C16	117.89 (14)
O1—C7—C6	125.99 (13)	F1—C15—C14	118.60 (14)
O1—C7—C2	110.55 (12)	C16—C15—C14	123.51 (14)
C6—C7—C2	123.46 (14)	C15—C16—C17	118.15 (13)
O1—C8—C1	110.32 (12)	C15—C16—H16	120.9
O1—C8—C11	115.33 (12)	C17—C16—H16	120.9
C1—C8—C11	134.35 (14)	C16—C17—C12	119.59 (13)
C4—C9—C10	112.95 (14)	C16—C17—H17	120.2
C4—C9—H9A	109.0	C12—C17—H17	120.2
C10—C9—H9A	109.0

O3—S1—C1—C8	−11.72 (15)	C7—O1—C8—C1	0.22 (15)
O2—S1—C1—C8	−142.73 (12)	C7—O1—C8—C11	179.75 (11)
C12—S1—C1—C8	103.23 (13)	C2—C1—C8—O1	−0.33 (15)
O3—S1—C1—C2	168.62 (11)	S1—C1—C8—O1	179.95 (9)
O2—S1—C1—C2	37.61 (13)	C2—C1—C8—C11	−179.74 (15)
C12—S1—C1—C2	−76.43 (12)	S1—C1—C8—C11	0.6 (2)
C8—C1—C2—C7	0.31 (14)	C3—C4—C9—C10	−86.77 (18)
S1—C1—C2—C7	−179.97 (10)	C5—C4—C9—C10	91.01 (18)
C8—C1—C2—C3	−178.43 (15)	O3—S1—C12—C17	24.49 (13)
S1—C1—C2—C3	1.3 (2)	O2—S1—C12—C17	154.16 (11)
C7—C2—C3—C4	0.01 (19)	C1—S1—C12—C17	−91.56 (12)
C1—C2—C3—C4	178.61 (14)	O3—S1—C12—C13	−153.99 (11)
C2—C3—C4—C5	0.9 (2)	O2—S1—C12—C13	−24.32 (13)
C2—C3—C4—C9	178.68 (13)	C1—S1—C12—C13	89.96 (12)
C3—C4—C5—C6	−0.9 (2)	C17—C12—C13—C14	0.7 (2)
C9—C4—C5—C6	−178.63 (14)	S1—C12—C13—C14	179.12 (11)
C4—C5—C6—C7	−0.1 (2)	C12—C13—C14—C15	−0.9 (2)
C8—O1—C7—C6	179.79 (13)	C13—C14—C15—F1	−179.79 (13)
C8—O1—C7—C2	−0.01 (15)	C13—C14—C15—C16	−0.1 (2)
C5—C6—C7—O1	−178.77 (13)	F1—C15—C16—C17	−178.93 (13)
C5—C6—C7—C2	1.0 (2)	C14—C15—C16—C17	1.4 (2)
C3—C2—C7—O1	178.81 (11)	C15—C16—C17—C12	−1.6 (2)
C1—C2—C7—O1	−0.18 (14)	C13—C12—C17—C16	0.6 (2)
C3—C2—C7—C6	−1.0 (2)	S1—C12—C17—C16	−177.84 (10)
C1—C2—C7—C6	−179.99 (13)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.40	3.3143 (17)	161
C11—H11C···Cgⁱⁱ	0.98	2.66	3.491 (2)	143

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FO₃S
M_r	318.35
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.0042 (1), 9.7114 (2), 11.3741 (2)
α, β, γ (°)	66.487 (1), 82.998 (1), 67.964 (1)
V (Å³)	751.10 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.31 × 0.25 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.929, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	13998, 3722, 3264
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.04
No. of reflections	3722
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.38

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

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.40	3.3143 (17)	161
C11—H11C···Cgⁱⁱ	0.98	2.66	3.491 (2)	143

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

Acknowledgements

This work was supported by Blue-Bio Industry RIC at Dongeui University as a RIC program under the Ministry of Knowledge Economy and the city of Busan.

References

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Volume 66| Part 10| October 2010| Page o2575

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