5-Chloro-2-phenyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536809028153

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1958

doi:10.1107/S1600536809028153

Open

access

5-Chloro-2-phenyl-3-phenylsulfinyl-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 July 2009; accepted 17 July 2009; online 22 July 2009)

In the title compound, C₂₀H₁₃ClO₂S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment; the S-bound phenyl ring is nearly perpendicular to this plane [80.87 (5)°]. The phenyl ring in the 2-position is rotated out of the benzofuran plane, making a dihedral angle of 17.43 (7)°. The crystal structure features π–π interactions between the phenyl ring and the furyl ring of a neighbouring benzofuran system [centroid–centroid distance = 3.886 (2) Å].

Related literature

For the crystal structures of similar 2-phenyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a ,b ). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ); Twyman & Allsop (1999 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); von Reuss & König (2004 ).

Experimental

Crystal data

C₂₀H₁₃ClO₂S
M_r = 352.81
Triclinic, $[P \overline 1]$
a = 8.2726 (5) Å
b = 9.4111 (5) Å
c = 11.3811 (6) Å
α = 73.360 (1)°
β = 81.630 (1)°
γ = 70.757 (1)°
V = 800.25 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 273 K
0.24 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.915, T_max = 0.963
6930 measured reflections
3428 independent reflections
2843 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.06
3428 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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/S1600536809028153/ng2614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028153/ng2614Isup2.hkl

checkCIF report

Comment top

Molecules containing the benzofuran skeleton have attracted considerable interest in view of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999) and are well known as natural products (Akgul & Anil, 2003; von Reuss & König, 2004). This work is related to our communications on the synthesis and structures of 2-phenyl-3-phenylsulfiny-1-benzofuran analogues, viz. 5-chloro-7-methyl-2-phenyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2009a) and 5-iodo-2-phenyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2009b). Here we report the crystal structure of the title compound (I), 5-chloro-2-phenyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.012 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle in (I) formed by the plane of the benzofuran ring and the plane of 2-phenyl ring is 17.43 (7)°, and the phenyl ring (C15-C20) with80.87 (5) ° lies toward the benzofuran plane. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the benzene ring and the furan ring from the neighbouring bennzofuran systems. The Cg1···Cg2ⁱ distance is 3.886 (2) Å (Cg1 and Cg2 are the centroides of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively).

Related literature top

For the crystal structures of similar 2-phenyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). For natural products with benzofuran rings, see: Akgul & Anil (2003); von Reuss & König (2004).

Experimental top

The 77% 3-chloroperoxybenzoic acid (157 mg, 0.7 mmol) was added in small portions to a stirred solution of 5-chloro-2-phenyl-3-phenylsulfanyl-1-benzofuran (226 mg, 0.7 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 421-422 K; R_f = 0.55 (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 benzene at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The π–π interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (i) - x + 1, - y + 1, -z.]

5-Chloro-2-phenyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₀H₁₃ClO₂S	Z = 2
M_r = 352.81	F(000) = 364
Triclinic, P1	D_x = 1.464 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2726 (5) Å	Cell parameters from 4091 reflections
b = 9.4111 (5) Å	θ = 2.4–27.4°
c = 11.3811 (6) Å	µ = 0.38 mm⁻¹
α = 73.360 (1)°	T = 273 K
β = 81.630 (1)°	Block, colorless
γ = 70.757 (1)°	0.24 × 0.15 × 0.10 mm
V = 800.25 (8) Å³

Data collection top

Bruker SMART CCD diffractometer	3428 independent reflections
Radiation source: fine-focus sealed tube	2843 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −11→11
T_min = 0.915, T_max = 0.963	l = −14→14
6930 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0423P)² + 0.2959P] where P = (F_o² + 2F_c²)/3
3428 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₀H₁₃ClO₂S	γ = 70.757 (1)°
M_r = 352.81	V = 800.25 (8) Å³
Triclinic, P1	Z = 2
a = 8.2726 (5) Å	Mo Kα radiation
b = 9.4111 (5) Å	µ = 0.38 mm⁻¹
c = 11.3811 (6) Å	T = 273 K
α = 73.360 (1)°	0.24 × 0.15 × 0.10 mm
β = 81.630 (1)°

Data collection top

Bruker SMART CCD diffractometer	3428 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2843 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.963	R_int = 0.016
6930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	Δρ_max = 0.29 e Å⁻³
3428 reflections	Δρ_min = −0.32 e Å⁻³
217 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
S	0.60764 (5)	0.10727 (5)	0.36530 (4)	0.03141 (12)
Cl	1.01634 (7)	0.23915 (6)	−0.11687 (4)	0.04741 (15)
O1	0.50587 (16)	0.56115 (13)	0.20476 (11)	0.0353 (3)
O2	0.78018 (15)	0.00894 (15)	0.33104 (13)	0.0442 (3)
C1	0.5863 (2)	0.29999 (19)	0.27413 (15)	0.0299 (4)
C2	0.6787 (2)	0.33818 (19)	0.15726 (15)	0.0308 (4)
C3	0.7989 (2)	0.2542 (2)	0.08331 (16)	0.0336 (4)
H3	0.8357	0.1460	0.1047	0.040*
C4	0.8610 (2)	0.3395 (2)	−0.02336 (17)	0.0368 (4)
C5	0.8064 (3)	0.5023 (2)	−0.05899 (17)	0.0415 (4)
H5	0.8517	0.5545	−0.1317	0.050*
C6	0.6860 (3)	0.5857 (2)	0.01297 (17)	0.0401 (4)
H6	0.6476	0.6939	−0.0094	0.048*
C7	0.6246 (2)	0.5006 (2)	0.12049 (16)	0.0331 (4)
C8	0.4853 (2)	0.4365 (2)	0.29930 (15)	0.0314 (4)
C9	0.3623 (2)	0.4786 (2)	0.39888 (16)	0.0325 (4)
C10	0.3580 (3)	0.3731 (2)	0.51308 (17)	0.0391 (4)
H10	0.4347	0.2730	0.5270	0.047*
C11	0.2402 (3)	0.4167 (2)	0.60561 (18)	0.0435 (5)
H11	0.2382	0.3455	0.6814	0.052*
C12	0.1258 (3)	0.5644 (3)	0.58682 (19)	0.0465 (5)
H12	0.0467	0.5927	0.6494	0.056*
C13	0.1293 (3)	0.6706 (3)	0.4743 (2)	0.0515 (5)
H13	0.0527	0.7707	0.4612	0.062*
C14	0.2462 (2)	0.6280 (2)	0.38153 (19)	0.0445 (5)
H14	0.2477	0.7001	0.3062	0.053*
C15	0.4533 (2)	0.07047 (18)	0.29161 (15)	0.0286 (3)
C16	0.5052 (2)	−0.0090 (2)	0.20082 (17)	0.0384 (4)
H16	0.6205	−0.0422	0.1756	0.046*
C17	0.3826 (3)	−0.0381 (2)	0.14814 (19)	0.0467 (5)
H17	0.4156	−0.0906	0.0865	0.056*
C18	0.2127 (3)	0.0101 (2)	0.1865 (2)	0.0482 (5)
H18	0.1313	−0.0090	0.1498	0.058*
C19	0.1615 (2)	0.0868 (2)	0.2791 (2)	0.0444 (5)
H19	0.0464	0.1177	0.3053	0.053*
C20	0.2819 (2)	0.1173 (2)	0.33250 (17)	0.0352 (4)
H20	0.2488	0.1684	0.3950	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0263 (2)	0.0282 (2)	0.0325 (2)	−0.00846 (16)	−0.00388 (16)	0.00459 (16)
Cl	0.0486 (3)	0.0557 (3)	0.0388 (3)	−0.0223 (2)	0.0101 (2)	−0.0119 (2)
O1	0.0398 (7)	0.0282 (6)	0.0336 (7)	−0.0129 (5)	−0.0012 (5)	0.0010 (5)
O2	0.0248 (6)	0.0357 (7)	0.0569 (9)	−0.0031 (5)	−0.0028 (6)	0.0047 (6)
C1	0.0275 (8)	0.0290 (8)	0.0309 (9)	−0.0122 (7)	−0.0048 (7)	0.0017 (7)
C2	0.0285 (8)	0.0323 (9)	0.0303 (8)	−0.0141 (7)	−0.0056 (7)	0.0017 (7)
C3	0.0313 (9)	0.0341 (9)	0.0338 (9)	−0.0136 (7)	−0.0027 (7)	−0.0014 (7)
C4	0.0339 (9)	0.0427 (10)	0.0338 (9)	−0.0160 (8)	−0.0011 (7)	−0.0051 (8)
C5	0.0477 (11)	0.0449 (11)	0.0312 (9)	−0.0245 (9)	0.0013 (8)	0.0017 (8)
C6	0.0480 (11)	0.0323 (9)	0.0368 (10)	−0.0185 (8)	−0.0035 (8)	0.0041 (8)
C7	0.0335 (9)	0.0327 (9)	0.0311 (9)	−0.0136 (7)	−0.0034 (7)	−0.0001 (7)
C8	0.0316 (9)	0.0312 (9)	0.0303 (9)	−0.0150 (7)	−0.0063 (7)	0.0026 (7)
C9	0.0312 (9)	0.0331 (9)	0.0339 (9)	−0.0138 (7)	−0.0043 (7)	−0.0039 (7)
C10	0.0450 (10)	0.0333 (9)	0.0360 (10)	−0.0122 (8)	−0.0019 (8)	−0.0039 (8)
C11	0.0494 (11)	0.0456 (11)	0.0334 (10)	−0.0181 (9)	0.0022 (8)	−0.0047 (8)
C12	0.0405 (11)	0.0521 (12)	0.0458 (11)	−0.0154 (9)	0.0082 (9)	−0.0147 (9)
C13	0.0420 (11)	0.0415 (11)	0.0579 (13)	−0.0026 (9)	0.0036 (10)	−0.0075 (10)
C14	0.0393 (10)	0.0386 (10)	0.0432 (11)	−0.0077 (8)	0.0002 (8)	0.0024 (8)
C15	0.0277 (8)	0.0218 (8)	0.0300 (8)	−0.0077 (6)	−0.0005 (6)	0.0025 (6)
C16	0.0398 (10)	0.0278 (9)	0.0408 (10)	−0.0072 (7)	0.0059 (8)	−0.0060 (7)
C17	0.0639 (14)	0.0327 (10)	0.0452 (11)	−0.0148 (9)	−0.0050 (10)	−0.0115 (8)
C18	0.0533 (12)	0.0337 (10)	0.0619 (13)	−0.0165 (9)	−0.0204 (10)	−0.0063 (9)
C19	0.0290 (9)	0.0413 (11)	0.0610 (13)	−0.0122 (8)	−0.0040 (9)	−0.0075 (9)
C20	0.0297 (9)	0.0335 (9)	0.0398 (10)	−0.0094 (7)	0.0006 (7)	−0.0069 (8)

Geometric parameters (Å, º) top

S—O2	1.4898 (13)	C10—C11	1.383 (3)
S—C1	1.7782 (16)	C10—H10	0.9300
S—C15	1.7953 (17)	C11—C12	1.376 (3)
Cl—C4	1.7471 (19)	C11—H11	0.9300
O1—C7	1.371 (2)	C12—C13	1.384 (3)
O1—C8	1.3850 (19)	C12—H12	0.9300
C1—C8	1.365 (2)	C13—C14	1.378 (3)
C1—C2	1.447 (2)	C13—H13	0.9300
C2—C3	1.393 (2)	C14—H14	0.9300
C2—C7	1.396 (2)	C15—C16	1.383 (3)
C3—C4	1.384 (2)	C15—C20	1.391 (2)
C3—H3	0.9300	C16—C17	1.385 (3)
C4—C5	1.400 (3)	C16—H16	0.9300
C5—C6	1.376 (3)	C17—C18	1.374 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.386 (2)	C18—C19	1.384 (3)
C6—H6	0.9300	C18—H18	0.9300
C8—C9	1.460 (2)	C19—C20	1.382 (3)
C9—C14	1.395 (3)	C19—H19	0.9300
C9—C10	1.395 (2)	C20—H20	0.9300

O2—S—C1	106.48 (8)	C11—C10—H10	119.8
O2—S—C15	107.16 (8)	C9—C10—H10	119.8
C1—S—C15	97.09 (7)	C12—C11—C10	120.71 (18)
C7—O1—C8	106.97 (13)	C12—C11—H11	119.6
C8—C1—C2	107.66 (14)	C10—C11—H11	119.6
C8—C1—S	127.92 (13)	C11—C12—C13	119.62 (19)
C2—C1—S	124.42 (13)	C11—C12—H12	120.2
C3—C2—C7	119.65 (15)	C13—C12—H12	120.2
C3—C2—C1	135.69 (16)	C14—C13—C12	120.05 (19)
C7—C2—C1	104.66 (15)	C14—C13—H13	120.0
C4—C3—C2	116.86 (16)	C12—C13—H13	120.0
C4—C3—H3	121.6	C13—C14—C9	121.03 (18)
C2—C3—H3	121.6	C13—C14—H14	119.5
C3—C4—C5	122.95 (18)	C9—C14—H14	119.5
C3—C4—Cl	118.45 (15)	C16—C15—C20	121.14 (17)
C5—C4—Cl	118.60 (14)	C16—C15—S	120.62 (13)
C6—C5—C4	120.37 (16)	C20—C15—S	118.17 (13)
C6—C5—H5	119.8	C15—C16—C17	118.89 (18)
C4—C5—H5	119.8	C15—C16—H16	120.6
C5—C6—C7	116.83 (17)	C17—C16—H16	120.6
C5—C6—H6	121.6	C18—C17—C16	120.34 (19)
C7—C6—H6	121.6	C18—C17—H17	119.8
O1—C7—C6	125.88 (16)	C16—C17—H17	119.8
O1—C7—C2	110.78 (14)	C17—C18—C19	120.68 (19)
C6—C7—C2	123.33 (17)	C17—C18—H18	119.7
C1—C8—O1	109.91 (15)	C19—C18—H18	119.7
C1—C8—C9	135.11 (15)	C20—C19—C18	119.80 (19)
O1—C8—C9	114.96 (15)	C20—C19—H19	120.1
C14—C9—C10	118.28 (17)	C18—C19—H19	120.1
C14—C9—C8	119.98 (16)	C19—C20—C15	119.13 (18)
C10—C9—C8	121.73 (16)	C19—C20—H20	120.4
C11—C10—C9	120.32 (18)	C15—C20—H20	120.4

O2—S—C1—C8	−154.75 (16)	C7—O1—C8—C1	−1.18 (18)
C15—S—C1—C8	94.95 (17)	C7—O1—C8—C9	180.00 (14)
O2—S—C1—C2	24.56 (16)	C1—C8—C9—C14	−162.7 (2)
C15—S—C1—C2	−85.74 (15)	O1—C8—C9—C14	15.7 (2)
C8—C1—C2—C3	179.49 (19)	C1—C8—C9—C10	18.0 (3)
S—C1—C2—C3	0.1 (3)	O1—C8—C9—C10	−163.57 (16)
C8—C1—C2—C7	0.36 (18)	C14—C9—C10—C11	0.5 (3)
S—C1—C2—C7	−179.07 (12)	C8—C9—C10—C11	179.81 (17)
C7—C2—C3—C4	1.3 (2)	C9—C10—C11—C12	−0.1 (3)
C1—C2—C3—C4	−177.78 (18)	C10—C11—C12—C13	−0.3 (3)
C2—C3—C4—C5	−1.0 (3)	C11—C12—C13—C14	0.3 (3)
C2—C3—C4—Cl	178.31 (13)	C12—C13—C14—C9	0.0 (3)
C3—C4—C5—C6	0.2 (3)	C10—C9—C14—C13	−0.5 (3)
Cl—C4—C5—C6	−179.13 (15)	C8—C9—C14—C13	−179.77 (19)
C4—C5—C6—C7	0.4 (3)	O2—S—C15—C16	−12.69 (15)
C8—O1—C7—C6	−178.23 (17)	C1—S—C15—C16	97.05 (14)
C8—O1—C7—C2	1.43 (18)	O2—S—C15—C20	164.24 (13)
C5—C6—C7—O1	179.52 (17)	C1—S—C15—C20	−86.02 (14)
C5—C6—C7—C2	−0.1 (3)	C20—C15—C16—C17	1.7 (3)
C3—C2—C7—O1	179.59 (14)	S—C15—C16—C17	178.56 (13)
C1—C2—C7—O1	−1.11 (19)	C15—C16—C17—C18	−0.6 (3)
C3—C2—C7—C6	−0.7 (3)	C16—C17—C18—C19	−0.7 (3)
C1—C2—C7—C6	178.56 (17)	C17—C18—C19—C20	0.9 (3)
C2—C1—C8—O1	0.50 (19)	C18—C19—C20—C15	0.2 (3)
S—C1—C8—O1	179.91 (12)	C16—C15—C20—C19	−1.6 (2)
C2—C1—C8—C9	178.98 (18)	S—C15—C20—C19	−178.46 (13)
S—C1—C8—C9	−1.6 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃ClO₂S
M_r	352.81
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	8.2726 (5), 9.4111 (5), 11.3811 (6)
α, β, γ (°)	73.360 (1), 81.630 (1), 70.757 (1)
V (Å³)	800.25 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.24 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.915, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	6930, 3428, 2843
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.06
No. of reflections	3428
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o1767. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1809. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289. Web of Science CrossRef PubMed CAS Google Scholar
Reuss, S. H. von & König, W. A. (2004). Phytochemistry, 65, 3113–3118. Web of Science PubMed Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384. Web of Science CrossRef CAS Google Scholar