5-Bromo-3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536810027741

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2049

https://doi.org/10.1107/S1600536810027741

Open

access

5-Bromo-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 6 July 2010; accepted 13 July 2010; online 17 July 2010)

In the title compound, C₁₅H₁₀BrFO₃S, the 4-fluorophenyl ring makes a dihedral angle of 76.51 (6)° with the plane of the benzofuran fragment. In the crystal, molecules are linked by weak non-classical intermolecular C—H⋯O hydrogen bonds and an aromatic π–π interaction between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.540 (3) Å].

Related literature

For the pharmacological 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 ). For the structures of related 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ,b ,c ).

Experimental

Crystal data

C₁₅H₁₀BrFO₃S
M_r = 369.20
Triclinic, $[P \overline 1]$
a = 7.4519 (3) Å
b = 9.2313 (4) Å
c = 11.4570 (5) Å
α = 70.652 (2)°
β = 78.495 (2)°
γ = 68.371 (2)°
V = 688.57 (5) Å³
Z = 2
Mo Kα radiation
μ = 3.15 mm⁻¹
T = 174 K
0.35 × 0.33 × 0.31 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.405, T_max = 0.439
11771 measured reflections
3137 independent reflections
2741 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.082
S = 1.08
3137 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3ⁱ	0.95	2.49	3.362 (3)	152
C11—H11⋯O2ⁱⁱ	0.95	2.67	3.345 (3)	128
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -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: https://doi.org/10.1107/S1600536810027741/rk2220sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027741/rk2220Isup2.hkl

checkCIF report

Comment top

Many compounds containing a benzofuran moiety show diverse pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report the molecular structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 (2)Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 76.51 (6)°. The molecular packing (Fig. 2) is stabilized by a weak intermolecular non-classical C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit, with a C15—H15···O3ⁱ (Table 1). The crystal packing (Fig. 2) is further stabilized by an aromatic π–π interaction between the benzene rings of neighbouring molecules, with a Cg···Cgⁱⁱ distance of 3.540 (3)Å (Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the pharmacological 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). For the structures of related 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c).

Experimental top

The 77% 3-chloroperoxybenzoic acid (493 mg, 2.2 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (337 mg, 1.0 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10 h, 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, 2:1 v/v) to afford the title compound as a colourless solid [yield 74%, m.p. 459–460 K; R_f=0.68 (hexane–ethyl acetate, 2:1 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.

Structure description top

For the pharmacological 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). For the structures of related 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c).

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 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. Presentation of non-classical C—H···O and π–π interactions (dashed lines) in the crystal structure of the title compound. Cg denotes the ring centroid. Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z.

5-Bromo-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran top

Crystal data top

C₁₅H₁₀BrFO₃S	Z = 2
M_r = 369.20	F(000) = 368
Triclinic, P1	D_x = 1.781 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4519 (3) Å	Cell parameters from 7545 reflections
b = 9.2313 (4) Å	θ = 2.5–27.5°
c = 11.4570 (5) Å	µ = 3.15 mm⁻¹
α = 70.652 (2)°	T = 174 K
β = 78.495 (2)°	Block, colourless
γ = 68.371 (2)°	0.35 × 0.33 × 0.31 mm
V = 688.57 (5) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3137 independent reflections
Radiation source: rotating anode	2741 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.040
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
φ– and ω–scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.405, T_max = 0.439	l = −14→14
11771 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0442P)² + 0.0824P] where P = (F_o² + 2F_c²)/3
3137 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₅H₁₀BrFO₃S	γ = 68.371 (2)°
M_r = 369.20	V = 688.57 (5) Å³
Triclinic, P1	Z = 2
a = 7.4519 (3) Å	Mo Kα radiation
b = 9.2313 (4) Å	µ = 3.15 mm⁻¹
c = 11.4570 (5) Å	T = 174 K
α = 70.652 (2)°	0.35 × 0.33 × 0.31 mm
β = 78.495 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3137 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2741 reflections with I > 2σ(I)
T_min = 0.405, T_max = 0.439	R_int = 0.040
11771 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.08	Δρ_max = 0.23 e Å⁻³
3137 reflections	Δρ_min = −0.58 e Å⁻³
191 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
Br	0.75115 (3)	0.08439 (3)	0.82425 (2)	0.04195 (10)
S	0.46680 (7)	0.39556 (6)	0.29542 (5)	0.02422 (12)
F	1.0254 (2)	0.73795 (18)	0.06607 (16)	0.0525 (4)
O1	0.7799 (2)	−0.06606 (16)	0.35232 (13)	0.0283 (3)
O2	0.3581 (2)	0.41371 (18)	0.19806 (14)	0.0315 (3)
O3	0.3671 (2)	0.44837 (18)	0.40280 (14)	0.0331 (3)
C1	0.6054 (3)	0.1915 (2)	0.34920 (18)	0.0244 (4)
C2	0.6740 (3)	0.1097 (2)	0.47105 (18)	0.0229 (4)
C3	0.6615 (3)	0.1518 (2)	0.57888 (18)	0.0258 (4)
H3	0.5897	0.2583	0.5852	0.031*
C4	0.7587 (3)	0.0310 (3)	0.67691 (19)	0.0273 (4)
C5	0.8637 (3)	−0.1268 (3)	0.6709 (2)	0.0304 (5)
H5	0.9269	−0.2057	0.7407	0.037*
C6	0.8759 (3)	−0.1687 (2)	0.5639 (2)	0.0293 (5)
H6	0.9468	−0.2754	0.5577	0.035*
C7	0.7807 (3)	−0.0488 (2)	0.46705 (19)	0.0249 (4)
C8	0.6742 (3)	0.0817 (2)	0.28167 (19)	0.0262 (4)
C9	0.6637 (3)	0.0903 (3)	0.1523 (2)	0.0356 (5)
H9A	0.5777	0.1978	0.1109	0.053*
H9B	0.6128	0.0067	0.1516	0.053*
H9C	0.7936	0.0722	0.1083	0.053*
C10	0.6374 (3)	0.4971 (2)	0.22804 (19)	0.0240 (4)
C11	0.6702 (3)	0.5460 (3)	0.0994 (2)	0.0305 (5)
H11	0.6034	0.5226	0.0491	0.037*
C12	0.8000 (3)	0.6283 (3)	0.0455 (2)	0.0373 (5)
H12	0.8227	0.6642	−0.0423	0.045*
C13	0.8962 (3)	0.6577 (3)	0.1208 (2)	0.0354 (5)
C14	0.8684 (3)	0.6105 (3)	0.2478 (2)	0.0343 (5)
H14	0.9387	0.6324	0.2969	0.041*
C15	0.7348 (3)	0.5297 (2)	0.3030 (2)	0.0283 (4)
H15	0.7103	0.4971	0.3908	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.04901 (16)	0.04935 (17)	0.02543 (14)	−0.00911 (12)	−0.01044 (10)	−0.01172 (11)
S	0.0240 (2)	0.0251 (3)	0.0201 (2)	−0.00436 (19)	−0.00352 (19)	−0.0053 (2)
F	0.0530 (9)	0.0482 (9)	0.0613 (10)	−0.0315 (7)	−0.0082 (7)	−0.0033 (8)
O1	0.0304 (7)	0.0261 (7)	0.0282 (8)	−0.0070 (6)	−0.0013 (6)	−0.0107 (6)
O2	0.0301 (7)	0.0349 (8)	0.0286 (8)	−0.0102 (6)	−0.0104 (6)	−0.0038 (7)
O3	0.0335 (8)	0.0316 (8)	0.0249 (8)	−0.0015 (6)	0.0021 (6)	−0.0091 (7)
C1	0.0239 (9)	0.0257 (10)	0.0216 (10)	−0.0067 (8)	−0.0014 (8)	−0.0060 (8)
C2	0.0202 (8)	0.0238 (10)	0.0231 (10)	−0.0077 (7)	−0.0004 (7)	−0.0050 (8)
C3	0.0264 (9)	0.0249 (10)	0.0232 (10)	−0.0062 (8)	−0.0019 (8)	−0.0058 (8)
C4	0.0239 (9)	0.0341 (11)	0.0226 (10)	−0.0098 (8)	−0.0026 (8)	−0.0060 (9)
C5	0.0269 (10)	0.0305 (11)	0.0276 (11)	−0.0086 (8)	−0.0053 (8)	0.0006 (9)
C6	0.0242 (9)	0.0231 (10)	0.0344 (12)	−0.0048 (8)	−0.0012 (9)	−0.0044 (9)
C7	0.0240 (9)	0.0260 (10)	0.0256 (10)	−0.0102 (8)	0.0003 (8)	−0.0076 (8)
C8	0.0254 (9)	0.0277 (10)	0.0241 (10)	−0.0078 (8)	−0.0022 (8)	−0.0064 (8)
C9	0.0418 (12)	0.0394 (13)	0.0278 (12)	−0.0100 (10)	−0.0040 (10)	−0.0154 (10)
C10	0.0256 (9)	0.0202 (9)	0.0245 (10)	−0.0037 (7)	−0.0048 (8)	−0.0069 (8)
C11	0.0368 (11)	0.0335 (11)	0.0242 (10)	−0.0135 (9)	−0.0076 (9)	−0.0070 (9)
C12	0.0432 (13)	0.0379 (13)	0.0295 (12)	−0.0179 (10)	−0.0021 (10)	−0.0036 (10)
C13	0.0363 (11)	0.0255 (11)	0.0456 (14)	−0.0126 (9)	−0.0061 (10)	−0.0072 (10)
C14	0.0358 (11)	0.0271 (11)	0.0459 (14)	−0.0074 (9)	−0.0137 (10)	−0.0153 (10)
C15	0.0323 (10)	0.0248 (10)	0.0253 (10)	−0.0005 (8)	−0.0084 (8)	−0.0105 (9)

Geometric parameters (Å, º) top

Br—C4	1.894 (2)	C6—C7	1.371 (3)
S—O2	1.4369 (15)	C6—H6	0.9500
S—O3	1.4385 (14)	C8—C9	1.474 (3)
S—C1	1.745 (2)	C9—H9A	0.9800
S—C10	1.760 (2)	C9—H9B	0.9800
F—C13	1.359 (3)	C9—H9C	0.9800
O1—C8	1.366 (2)	C10—C11	1.390 (3)
O1—C7	1.377 (2)	C10—C15	1.391 (3)
C1—C8	1.367 (3)	C11—C12	1.374 (3)
C1—C2	1.443 (3)	C11—H11	0.9500
C2—C3	1.390 (3)	C12—C13	1.370 (3)
C2—C7	1.396 (3)	C12—H12	0.9500
C3—C4	1.389 (3)	C13—C14	1.370 (3)
C3—H3	0.9500	C14—C15	1.390 (3)
C4—C5	1.394 (3)	C14—H14	0.9500
C5—C6	1.380 (3)	C15—H15	0.9500
C5—H5	0.9500

O2—S—O3	119.74 (9)	O1—C8—C1	110.28 (18)
O2—S—C1	108.91 (9)	O1—C8—C9	115.36 (17)
O3—S—C1	106.96 (9)	C1—C8—C9	134.3 (2)
O2—S—C10	107.49 (9)	C8—C9—H9A	109.5
O3—S—C10	107.99 (10)	C8—C9—H9B	109.5
C1—S—C10	104.78 (9)	H9A—C9—H9B	109.5
C8—O1—C7	107.04 (14)	C8—C9—H9C	109.5
C8—C1—C2	107.63 (17)	H9A—C9—H9C	109.5
C8—C1—S	125.95 (17)	H9B—C9—H9C	109.5
C2—C1—S	126.38 (15)	C11—C10—C15	120.92 (19)
C3—C2—C7	119.08 (18)	C11—C10—S	118.93 (16)
C3—C2—C1	136.46 (18)	C15—C10—S	120.14 (16)
C7—C2—C1	104.44 (17)	C12—C11—C10	119.6 (2)
C4—C3—C2	116.97 (18)	C12—C11—H11	120.2
C4—C3—H3	121.5	C10—C11—H11	120.2
C2—C3—H3	121.5	C13—C12—C11	118.7 (2)
C3—C4—C5	122.9 (2)	C13—C12—H12	120.7
C3—C4—Br	118.43 (15)	C11—C12—H12	120.7
C5—C4—Br	118.66 (16)	F—C13—C14	118.7 (2)
C6—C5—C4	120.1 (2)	F—C13—C12	118.0 (2)
C6—C5—H5	119.9	C14—C13—C12	123.4 (2)
C4—C5—H5	119.9	C13—C14—C15	118.3 (2)
C7—C6—C5	116.77 (18)	C13—C14—H14	120.9
C7—C6—H6	121.6	C15—C14—H14	120.9
C5—C6—H6	121.6	C14—C15—C10	119.2 (2)
C6—C7—O1	125.27 (18)	C14—C15—H15	120.4
C6—C7—C2	124.12 (19)	C10—C15—H15	120.4
O1—C7—C2	110.59 (17)

O2—S—C1—C8	28.0 (2)	C1—C2—C7—O1	0.0 (2)
O3—S—C1—C8	158.69 (18)	C7—O1—C8—C1	−1.0 (2)
C10—S—C1—C8	−86.8 (2)	C7—O1—C8—C9	177.27 (18)
O2—S—C1—C2	−154.43 (17)	C2—C1—C8—O1	0.9 (2)
O3—S—C1—C2	−23.7 (2)	S—C1—C8—O1	178.94 (14)
C10—S—C1—C2	90.80 (19)	C2—C1—C8—C9	−176.8 (2)
C8—C1—C2—C3	177.7 (2)	S—C1—C8—C9	1.2 (4)
S—C1—C2—C3	−0.3 (3)	O2—S—C10—C11	−12.64 (18)
C8—C1—C2—C7	−0.6 (2)	O3—S—C10—C11	−143.12 (15)
S—C1—C2—C7	−178.53 (15)	C1—S—C10—C11	103.12 (17)
C7—C2—C3—C4	0.3 (3)	O2—S—C10—C15	166.35 (15)
C1—C2—C3—C4	−177.8 (2)	O3—S—C10—C15	35.87 (18)
C2—C3—C4—C5	−0.6 (3)	C1—S—C10—C15	−77.89 (17)
C2—C3—C4—Br	178.41 (14)	C15—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	0.6 (3)	S—C10—C11—C12	178.67 (17)
Br—C4—C5—C6	−178.47 (15)	C10—C11—C12—C13	1.0 (3)
C4—C5—C6—C7	−0.1 (3)	C11—C12—C13—F	179.4 (2)
C5—C6—C7—O1	178.37 (18)	C11—C12—C13—C14	−0.6 (4)
C5—C6—C7—C2	−0.2 (3)	F—C13—C14—C15	179.46 (19)
C8—O1—C7—C6	−178.15 (19)	C12—C13—C14—C15	−0.5 (3)
C8—O1—C7—C2	0.6 (2)	C13—C14—C15—C10	1.2 (3)
C3—C2—C7—C6	0.1 (3)	C11—C10—C15—C14	−0.8 (3)
C1—C2—C7—C6	178.73 (19)	S—C10—C15—C14	−179.79 (15)
C3—C2—C7—O1	−178.63 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3ⁱ	0.95	2.49	3.362 (3)	152
C11—H11···O2ⁱⁱ	0.95	2.67	3.345 (3)	128

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrFO₃S
M_r	369.20
Crystal system, space group	Triclinic, P1
Temperature (K)	174
a, b, c (Å)	7.4519 (3), 9.2313 (4), 11.4570 (5)
α, β, γ (°)	70.652 (2), 78.495 (2), 68.371 (2)
V (Å³)	688.57 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.15
Crystal size (mm)	0.35 × 0.33 × 0.31

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.405, 0.439
No. of measured, independent and observed [I > 2σ(I)] reflections	11771, 3137, 2741
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.08
No. of reflections	3137
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.58

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
C15—H15···O3ⁱ	0.95	2.49	3.362 (3)	152.1
C11—H11···O2ⁱⁱ	0.95	2.67	3.345 (3)	128.2

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −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., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226. Web of Science CrossRef 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. (2010a). Acta Cryst. E66, o1067. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1813. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o1909. 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
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

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 66| Part 8| August 2010| Page o2049

https://doi.org/10.1107/S1600536810027741

Open

access