3-(4-Fluoro­phenyl­sulfin­yl)-2,4,6-trimethyl-1-benzofuran

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

doi:10.1107/S1600536810004836

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o586

doi:10.1107/S1600536810004836

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3-(4-Fluorophenylsulfinyl)-2,4,6-trimethyl-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 29 January 2010; accepted 7 February 2010; online 13 February 2010)

In the title compound, C₁₇H₁₅FO₂S, the O atom and the 4-fluorophenyl group of the 4-fluorophenylsulfinyl substituent lie on opposite sides of the plane of the benzofuran; the 4-fluorophenyl ring is almost perpendicular to this plane, making a dihedral angle of 88.99 (4)°. The crystal structure exhibits intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions between the methyl H atom and the 4-fluorophenyl ring.

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007 , 2008a ,b ). 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 ).

Experimental

Crystal data

C₁₇H₁₅FO₂S
M_r = 302.35
Orthorhombic, P n a 2₁
a = 11.9486 (4) Å
b = 18.8134 (9) Å
c = 6.4435 (3) Å
V = 1448.46 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.36 × 0.34 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.920, T_max = 0.947
6188 measured reflections
2147 independent reflections
2094 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.076
S = 1.05
2147 reflections
193 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 745 Friedel pairs
Flack parameter: 0.01 (8)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O2ⁱ	0.98	2.60	3.301 (3)	129
C10—H10C⋯Cgⁱⁱ	0.98	2.78	3.604 (3)	142
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) x, 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 datablock I. DOI: 10.1107/S1600536810004836/fk2013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004836/fk2013Isup2.hkl

checkCIF report

Comment top

Molecules containing benzofuran skeleton show significant pharmacological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties. These compounds are widely occurring in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-methyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2007, 2008a,b), we report the crystal 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 4-fluorophenyl ring is almost perpendicular to the plane of the benzofuran fragment [88.99 (4)°] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by an intermolecular C—H···O hydrogen bond between the methyl H atom and the oxygen of the S═O unit, with a C10—H10A···O2ⁱ (Table 1). The molecular packing (Fig. 2) is further stabilized by an intermolecular C—H···π interaction between the methyl H atom and the 4–fluorophenyl ring, with a C10—H10C···Cgⁱⁱ (Table 1; Cg is the centroid of the C11–C16 4-fluorophenyl ring).

Related literature top

For the crystal structures of similar 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007, 2008a,b). 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).

Experimental top

77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-2,4,6-trimethyl-1-benzofuran (257 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 82%, m.p. 410–411 K; R_f = 0.69 (hexane–ethyl acetate, 1:1 v/v)]. 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 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. C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: i) x - 1/2, - y + 1/2,z; ii) x, y, z + 1; iii) x + 1/2, - y + 1/2, z; iv) x, y, z - 1.]

3-(4-Fluorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅FO₂S	F(000) = 632
M_r = 302.35	D_x = 1.386 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5305 reflections
a = 11.9486 (4) Å	θ = 2.8–31.0°
b = 18.8134 (9) Å	µ = 0.24 mm⁻¹
c = 6.4435 (3) Å	T = 173 K
V = 1448.46 (11) Å³	Block, colourless
Z = 4	0.36 × 0.34 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2147 independent reflections
Radiation source: Rotating Anode	2094 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ϕ and ω scans	h = −13→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −22→9
T_min = 0.920, T_max = 0.947	l = −5→7
6188 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0501P)² + 0.2112P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2147 reflections	Δρ_max = 0.19 e Å⁻³
193 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 745 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (8)

Crystal data top

C₁₇H₁₅FO₂S	V = 1448.46 (11) Å³
M_r = 302.35	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.9486 (4) Å	µ = 0.24 mm⁻¹
b = 18.8134 (9) Å	T = 173 K
c = 6.4435 (3) Å	0.36 × 0.34 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2147 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2094 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.947	R_int = 0.027
6188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.19 e Å⁻³
S = 1.05	Δρ_min = −0.32 e Å⁻³
2147 reflections	Absolute structure: Flack (1983), 745 Friedel pairs
193 parameters	Absolute structure parameter: 0.01 (8)
1 restraint

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
S	0.58051 (3)	0.24745 (2)	0.81941 (12)	0.02603 (14)
F	0.48280 (12)	0.04865 (7)	0.1409 (3)	0.0569 (4)
O1	0.31672 (10)	0.36585 (6)	0.9109 (2)	0.0272 (3)
O2	0.69067 (10)	0.28105 (7)	0.7715 (3)	0.0352 (4)
C1	0.47298 (13)	0.31127 (8)	0.8012 (4)	0.0235 (4)
C2	0.44816 (14)	0.36764 (9)	0.6520 (3)	0.0232 (4)
C3	0.49438 (14)	0.39469 (9)	0.4673 (4)	0.0264 (4)
C4	0.43695 (16)	0.45042 (9)	0.3733 (3)	0.0307 (5)
H4	0.4664	0.4697	0.2485	0.037*
C5	0.33771 (15)	0.47965 (10)	0.4533 (4)	0.0321 (5)
C6	0.35091 (14)	0.39864 (9)	0.7305 (3)	0.0247 (4)
C18	0.29371 (15)	0.45395 (9)	0.6362 (4)	0.0299 (4)
H18	0.2274	0.4732	0.6948	0.036*
C7	0.39288 (14)	0.31267 (9)	0.9495 (3)	0.0250 (4)
C8	0.59776 (16)	0.36461 (11)	0.3682 (3)	0.0328 (5)
H8A	0.5784	0.3213	0.2919	0.049*
H8B	0.6529	0.3533	0.4759	0.049*
H8C	0.6294	0.3996	0.2721	0.049*
C9	0.27873 (19)	0.53802 (10)	0.3354 (5)	0.0480 (6)
H9A	0.2007	0.5411	0.3816	0.072*
H9B	0.2808	0.5275	0.1865	0.072*
H9C	0.3164	0.5834	0.3616	0.072*
C10	0.36932 (15)	0.26859 (10)	1.1344 (4)	0.0315 (4)
H10A	0.2985	0.2432	1.1146	0.047*
H10B	0.3638	0.2992	1.2571	0.047*
H10C	0.4300	0.2342	1.1540	0.047*
C11	0.54562 (14)	0.19223 (9)	0.6020 (3)	0.0247 (4)
C12	0.44150 (15)	0.15884 (10)	0.5924 (4)	0.0316 (5)
H12	0.3854	0.1694	0.6921	0.038*
C13	0.42097 (15)	0.11030 (11)	0.4364 (4)	0.0367 (5)
H13	0.3506	0.0870	0.4271	0.044*
C14	0.50423 (17)	0.09628 (9)	0.2943 (4)	0.0367 (5)
C15	0.60681 (16)	0.12901 (10)	0.2988 (4)	0.0340 (5)
H15	0.6618	0.1191	0.1963	0.041*
C16	0.62779 (14)	0.17706 (10)	0.4580 (4)	0.0299 (4)
H16	0.6988	0.1995	0.4678	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0224 (2)	0.0280 (2)	0.0277 (3)	0.00348 (15)	−0.0020 (2)	0.00368 (19)
F	0.0605 (8)	0.0523 (7)	0.0578 (11)	−0.0008 (6)	0.0001 (8)	−0.0262 (8)
O1	0.0251 (6)	0.0272 (6)	0.0294 (9)	0.0035 (4)	0.0020 (6)	−0.0003 (6)
O2	0.0207 (6)	0.0380 (7)	0.0469 (12)	−0.0016 (5)	−0.0048 (6)	0.0005 (7)
C1	0.0213 (7)	0.0236 (8)	0.0256 (11)	0.0000 (5)	−0.0015 (8)	0.0000 (8)
C2	0.0232 (7)	0.0227 (8)	0.0237 (10)	−0.0013 (6)	−0.0046 (8)	0.0008 (8)
C3	0.0277 (8)	0.0250 (9)	0.0264 (11)	−0.0062 (7)	−0.0046 (8)	0.0008 (8)
C4	0.0345 (9)	0.0278 (9)	0.0297 (13)	−0.0086 (7)	−0.0045 (9)	0.0064 (8)
C5	0.0313 (9)	0.0240 (9)	0.0411 (15)	−0.0026 (7)	−0.0115 (9)	0.0061 (9)
C6	0.0249 (8)	0.0232 (8)	0.0259 (11)	−0.0031 (6)	−0.0025 (8)	−0.0007 (7)
C18	0.0261 (8)	0.0224 (8)	0.0412 (13)	0.0013 (7)	−0.0048 (9)	−0.0016 (9)
C7	0.0236 (7)	0.0250 (8)	0.0263 (11)	−0.0003 (6)	−0.0036 (8)	0.0018 (8)
C8	0.0325 (9)	0.0369 (10)	0.0290 (14)	−0.0046 (7)	0.0037 (9)	0.0051 (9)
C9	0.0476 (12)	0.0365 (11)	0.0599 (19)	0.0043 (8)	−0.0101 (13)	0.0178 (12)
C10	0.0288 (9)	0.0373 (9)	0.0282 (12)	−0.0003 (8)	0.0027 (9)	0.0049 (10)
C11	0.0231 (8)	0.0227 (8)	0.0284 (12)	0.0047 (7)	0.0007 (8)	0.0058 (8)
C12	0.0261 (9)	0.0290 (9)	0.0398 (14)	−0.0007 (7)	0.0076 (9)	0.0029 (9)
C13	0.0320 (10)	0.0331 (10)	0.0449 (16)	−0.0055 (7)	0.0023 (10)	−0.0033 (10)
C14	0.0407 (10)	0.0287 (9)	0.0408 (15)	0.0047 (7)	0.0001 (10)	−0.0041 (10)
C15	0.0337 (9)	0.0356 (10)	0.0328 (13)	0.0087 (7)	0.0069 (11)	0.0006 (10)
C16	0.0227 (8)	0.0311 (9)	0.0360 (13)	0.0038 (7)	0.0035 (9)	0.0048 (9)

Geometric parameters (Å, º) top

S—O2	1.4925 (13)	C8—H8A	0.9800
S—C1	1.7625 (16)	C8—H8B	0.9800
S—C11	1.793 (2)	C8—H8C	0.9800
F—C14	1.358 (3)	C9—H9A	0.9800
O1—C7	1.375 (2)	C9—H9B	0.9800
O1—C6	1.378 (2)	C9—H9C	0.9800
C1—C7	1.353 (3)	C10—H10A	0.9800
C1—C2	1.462 (3)	C10—H10B	0.9800
C2—C6	1.395 (3)	C10—H10C	0.9800
C2—C3	1.407 (3)	C11—C16	1.380 (3)
C3—C4	1.392 (3)	C11—C12	1.395 (2)
C3—C8	1.501 (3)	C12—C13	1.380 (3)
C4—C5	1.405 (3)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.377 (3)
C5—C18	1.378 (3)	C13—H13	0.9500
C5—C9	1.510 (3)	C14—C15	1.372 (3)
C6—C18	1.385 (3)	C15—C16	1.390 (3)
C18—H18	0.9500	C15—H15	0.9500
C7—C10	1.478 (3)	C16—H16	0.9500

O2—S—C1	109.91 (8)	H8A—C8—H8C	109.5
O2—S—C11	106.78 (9)	H8B—C8—H8C	109.5
C1—S—C11	99.97 (9)	C5—C9—H9A	109.5
C7—O1—C6	106.39 (14)	C5—C9—H9B	109.5
C7—C1—C2	107.87 (15)	H9A—C9—H9B	109.5
C7—C1—S	118.82 (15)	C5—C9—H9C	109.5
C2—C1—S	133.31 (15)	H9A—C9—H9C	109.5
C6—C2—C3	118.82 (16)	H9B—C9—H9C	109.5
C6—C2—C1	103.55 (17)	C7—C10—H10A	109.5
C3—C2—C1	137.63 (17)	C7—C10—H10B	109.5
C4—C3—C2	116.55 (18)	H10A—C10—H10B	109.5
C4—C3—C8	120.3 (2)	C7—C10—H10C	109.5
C2—C3—C8	123.12 (17)	H10A—C10—H10C	109.5
C3—C4—C5	123.5 (2)	H10B—C10—H10C	109.5
C3—C4—H4	118.3	C16—C11—C12	120.76 (19)
C5—C4—H4	118.3	C16—C11—S	118.65 (14)
C18—C5—C4	119.89 (18)	C12—C11—S	120.18 (16)
C18—C5—C9	120.50 (19)	C13—C12—C11	119.26 (19)
C4—C5—C9	119.6 (2)	C13—C12—H12	120.4
O1—C6—C18	124.05 (17)	C11—C12—H12	120.4
O1—C6—C2	111.43 (15)	C14—C13—C12	118.84 (17)
C18—C6—C2	124.49 (19)	C14—C13—H13	120.6
C5—C18—C6	116.76 (17)	C12—C13—H13	120.6
C5—C18—H18	121.6	F—C14—C15	118.7 (2)
C6—C18—H18	121.6	F—C14—C13	118.28 (18)
C1—C7—O1	110.76 (17)	C15—C14—C13	123.0 (2)
C1—C7—C10	133.87 (17)	C14—C15—C16	118.0 (2)
O1—C7—C10	115.33 (16)	C14—C15—H15	121.0
C3—C8—H8A	109.5	C16—C15—H15	121.0
C3—C8—H8B	109.5	C11—C16—C15	120.13 (17)
H8A—C8—H8B	109.5	C11—C16—H16	119.9
C3—C8—H8C	109.5	C15—C16—H16	119.9

O2—S—C1—C7	−136.51 (15)	C9—C5—C18—C6	177.70 (19)
C11—S—C1—C7	111.44 (17)	O1—C6—C18—C5	−178.39 (17)
O2—S—C1—C2	43.3 (2)	C2—C6—C18—C5	−0.5 (3)
C11—S—C1—C2	−68.77 (19)	C2—C1—C7—O1	−0.2 (2)
C7—C1—C2—C6	0.1 (2)	S—C1—C7—O1	179.66 (12)
S—C1—C2—C6	−179.73 (15)	C2—C1—C7—C10	177.4 (2)
C7—C1—C2—C3	−179.6 (2)	S—C1—C7—C10	−2.8 (3)
S—C1—C2—C3	0.6 (4)	C6—O1—C7—C1	0.2 (2)
C6—C2—C3—C4	−1.3 (3)	C6—O1—C7—C10	−177.86 (16)
C1—C2—C3—C4	178.3 (2)	O2—S—C11—C16	13.49 (17)
C6—C2—C3—C8	−179.13 (17)	C1—S—C11—C16	127.95 (15)
C1—C2—C3—C8	0.5 (4)	O2—S—C11—C12	−173.86 (14)
C2—C3—C4—C5	−0.1 (3)	C1—S—C11—C12	−59.40 (17)
C8—C3—C4—C5	177.82 (18)	C16—C11—C12—C13	−0.2 (3)
C3—C4—C5—C18	1.2 (3)	S—C11—C12—C13	−172.66 (16)
C3—C4—C5—C9	−177.43 (19)	C11—C12—C13—C14	0.0 (3)
C7—O1—C6—C18	178.01 (18)	C12—C13—C14—F	−179.69 (19)
C7—O1—C6—C2	−0.16 (19)	C12—C13—C14—C15	−0.8 (4)
C3—C2—C6—O1	179.81 (15)	F—C14—C15—C16	−179.36 (19)
C1—C2—C6—O1	0.05 (19)	C13—C14—C15—C16	1.7 (3)
C3—C2—C6—C18	1.7 (3)	C12—C11—C16—C15	1.2 (3)
C1—C2—C6—C18	−178.11 (18)	S—C11—C16—C15	173.77 (15)
C4—C5—C18—C6	−1.0 (3)	C14—C15—C16—C11	−1.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2ⁱ	0.98	2.60	3.301 (3)	129
C10—H10C···Cgⁱⁱ	0.98	2.78	3.604 (3)	142

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FO₂S
M_r	302.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	11.9486 (4), 18.8134 (9), 6.4435 (3)
V (Å³)	1448.46 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.36 × 0.34 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.920, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	6188, 2147, 2094
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.05
No. of reflections	2147
No. of parameters	193
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.32
Absolute structure	Flack (1983), 745 Friedel pairs
Absolute structure parameter	0.01 (8)

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 C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2ⁱ	0.98	2.60	3.301 (3)	128.7
C10—H10C···Cgⁱⁱ	0.98	2.78	3.604 (3)	142.4

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

References

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Volume 66| Part 3| March 2010| Page o586

doi:10.1107/S1600536810004836

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