3,9-Dimethyl-2,3-dihydro­phenanthro[1,2-b]furan-4,5-dione

Yao, J.-C.; Wang, Z.-D.; Guo, J.-B.; Zhang, L.

doi:10.1107/S1600536809047667

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3106

doi:10.1107/S1600536809047667

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3,9-Dimethyl-2,3-dihydrophenanthro[1,2-b]furan-4,5-dione

Jing-Cai Yao,^a ^* Zhong-Dong Wang,^b Jin-Bo Guo ^a and Li Zhang ^a

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, and ^bLuoyang Zisheng Science & Technology Co Ltd, Luoyang 471000, People's Republic of China
^*Correspondence e-mail: yjc@lynu.edu.cn

(Received 18 August 2009; accepted 11 November 2009; online 18 November 2009)

The title compound, C₁₈H₁₄O₃, consists of a four-ring system which contains three six-membered rings forming a phenanthrenedione system and a five-membered 1,2-dihydromethylfuran ring. A three-dimensional supramolecular framework is formed via non-classical intermolecular C—H⋯O hydrogen bonds.

Related literature

For tanshinone compounds, see: Chang et al. (1991 ); Ryu et al. (1997 ); Xue et al. (1999 ); Yagi et al. (1989 ); Zhang et al. (2005 ); Zhu & Luo (2004 ).

Experimental

Crystal data

C₁₈H₁₄O₃
M_r = 278.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.6415 (10) Å
b = 14.692 (3) Å
c = 19.633 (4) Å
V = 1338.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.25 × 0.10 × 0.05 mm

Data collection

Bruker or SMART APEXdiffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.977, T_max = 0.995
6925 measured reflections
2502 independent reflections
1140 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.077
S = 1.03
2502 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯O1ⁱ	0.96	2.53	3.379 (4)	147
C16—H16A⋯O2ⁱ	0.97	2.48	3.384 (5)	155
C17—H17A⋯O2ⁱⁱ	0.96	2.56	3.484 (4)	162
C17—H17C⋯O2ⁱⁱⁱ	0.96	2.66	3.377 (4)	132
C7—H7⋯O3^iv	0.93	2.67	3.481 (4)	146
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{5\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047667/rk2163sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047667/rk2163Isup2.hkl

checkCIF report

Comment top

The Chinese herbal medicine, Danshen, is the dried rhizome of Salviae Miltiorrhiza Bunge and Salvia Przewalskii Maxim (Labiatae). It contains two parts of efective components (liposoluble tanshinones and aqueous-soluble salvianolic acids). Up to date, 41 tanshinones and 18 salvianolic acids have been extracted and reported. Tanshinones have been widely used in China to treat coronary heart diseases (Chang et al., 1991), antibacterial (Zhu et al., 2004), antitumour (Ryu et al., 1997), angina pectoris and myocardial infarction (Xue et al., 1999), cerebrovascular and neurasthenic insomnia problems (Yagi et al., 1989).

The title compound, C₁₈H₁₄O₃, (I) consists of a four-ring system in which contains three six-membered rings forming a phenanthrene-dione system, and a five-membered 1,2-dihydro-methylfuran ring (Fig. 1). The whole molecule is essentially planar, with a torsion angle C15—C13—C14—O3 = 0.40 (4)° in the furan ring, the torsion angles C1—C2—C3—C4 = 0.01 (6)° and C4—C5—C6—C1 = -1.80 (5)° from the terminal six-membered ring. In the structure, is similar to reported (Zhang et al., 2005) for 1,6-dimethylphenanthro[1,2-b]furan-10,11-dione, the C11—C12 bond distance agree with the corresponding distance of 1.566 (2)Å. Intermolecular C—H···O non-classical hydrogen bonds are observed in the crystal structure (Table 1), which form a three-dimensional supramolecular framework (Fig. 2).

Related literature top

For tanshinone compounds, see: Chang et al. (1991); Ryu et al. (1997); Xue et al. (1999); Yagi et al. (1989); Zhang et al. (2005); Zhu et al. (2004). [SCHEME: revise to show two methyl groups]

Experimental top

All reagents were of AR grade and were used without further purification. Dried powder of Salvia miltiorrhiza Bunge was exacted with EtOH and the extract was concentrated in vacuo. The residue was subjected to silica gel coloumn chromatography. Elution with petroleum ether–ethyl acetate (9:1 v/v) yielded the title compound. Elemental analysis - found: C, 77.68 %; H, 5.07 %; calc. for C₁₈H₁₄O₃: C, 77.14 %; H, 5.05 %.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of I, showing the atom-numbering scheme. The displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Intermolecular C—H···O non-classical hydrogen bonds and three-dimensional supramolecular framework in the crystal structure.

3,9-Dimethyl-2,3-dihydrophenanthro[1,2-b]furan-4,5-dione top

Crystal data top

C₁₈H₁₄O₃	F(000) = 584
M_r = 278.29	D_x = 1.381 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 634 reflections
a = 4.6415 (10) Å	θ = 2.5–18.2°
b = 14.692 (3) Å	µ = 0.09 mm⁻¹
c = 19.633 (4) Å	T = 295 K
V = 1338.8 (5) Å³	Block, yellow
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	2502 independent reflections
Radiation source: fine-focus sealed tube	1140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→5
T_min = 0.977, T_max = 0.995	k = −16→17
6925 measured reflections	l = −23→21

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0115P)²] where P = (F_o² + 2F_c²)/3
2502 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₁₄O₃	V = 1338.8 (5) Å³
M_r = 278.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.6415 (10) Å	µ = 0.09 mm⁻¹
b = 14.692 (3) Å	T = 295 K
c = 19.633 (4) Å	0.25 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	2502 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1140 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.995	R_int = 0.079
6925 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
2502 reflections	Δρ_min = −0.26 e Å⁻³
192 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
O1	0.9141 (6)	0.38978 (16)	0.80968 (12)	0.0805 (9)
O2	0.5033 (6)	0.47076 (16)	0.73687 (12)	0.0795 (9)
O3	0.5747 (6)	0.72625 (16)	0.87005 (12)	0.0692 (8)
C1	1.4263 (9)	0.4722 (3)	1.04455 (18)	0.0556 (10)
C2	1.5314 (9)	0.3891 (3)	1.03047 (19)	0.0667 (12)
H2	1.6605	0.3621	1.0605	0.080*
C3	1.4497 (9)	0.3423 (2)	0.9711 (2)	0.0657 (12)
H3	1.5261	0.2849	0.9628	0.079*
C4	1.2618 (8)	0.3789 (2)	0.92557 (19)	0.0569 (11)
H4	1.2110	0.3464	0.8867	0.068*
C5	1.1438 (8)	0.4660 (2)	0.93705 (17)	0.0448 (10)
C6	1.2314 (8)	0.5139 (3)	0.99724 (17)	0.0467 (10)
C7	1.1235 (9)	0.6017 (3)	1.00860 (17)	0.0574 (11)
H7	1.1801	0.6331	1.0475	0.069*
C8	0.9366 (9)	0.6424 (2)	0.96396 (18)	0.0597 (12)
H8	0.8690	0.7009	0.9724	0.072*
C9	0.8490 (8)	0.5959 (2)	0.90615 (18)	0.0485 (10)
C10	0.9455 (8)	0.5084 (2)	0.89194 (16)	0.0441 (9)
C11	0.8348 (8)	0.4632 (3)	0.82957 (18)	0.0508 (10)
C12	0.6103 (9)	0.5125 (2)	0.78450 (18)	0.0547 (11)
C13	0.5429 (8)	0.6037 (2)	0.80144 (18)	0.0482 (10)
C14	0.6529 (8)	0.6393 (2)	0.8583 (2)	0.0514 (11)
C15	0.3586 (8)	0.6724 (2)	0.76485 (18)	0.0610 (11)
H15	0.1590	0.6507	0.7634	0.073*
C16	0.3806 (9)	0.7536 (3)	0.81363 (19)	0.0889 (14)
H16A	0.4581	0.8062	0.7901	0.107*
H16B	0.1917	0.7692	0.8313	0.107*
C17	1.5136 (8)	0.5226 (3)	1.10832 (15)	0.0772 (13)
H17A	1.3472	0.5322	1.1365	0.116*
H17B	1.5959	0.5803	1.0962	0.116*
H17C	1.6532	0.4873	1.1329	0.116*
C18	0.4609 (9)	0.6927 (2)	0.69344 (17)	0.0875 (15)
H18A	0.6569	0.7135	0.6949	0.131*
H18B	0.3414	0.7391	0.6737	0.131*
H18C	0.4494	0.6385	0.6663	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.106 (2)	0.0545 (17)	0.0810 (19)	0.0212 (18)	−0.0224 (18)	−0.0241 (15)
O2	0.096 (2)	0.0665 (18)	0.0754 (19)	−0.0015 (18)	−0.0249 (18)	−0.0080 (16)
O3	0.089 (2)	0.0457 (16)	0.0727 (18)	0.0135 (17)	−0.0073 (16)	−0.0040 (14)
C1	0.053 (3)	0.065 (3)	0.049 (3)	−0.011 (3)	0.000 (2)	−0.001 (2)
C2	0.064 (3)	0.074 (3)	0.062 (3)	0.004 (3)	−0.005 (2)	0.007 (3)
C3	0.070 (3)	0.053 (3)	0.073 (3)	0.010 (3)	−0.002 (3)	−0.002 (2)
C4	0.063 (3)	0.047 (3)	0.061 (3)	0.005 (2)	−0.001 (2)	−0.003 (2)
C5	0.044 (2)	0.044 (2)	0.047 (2)	−0.008 (2)	0.009 (2)	0.001 (2)
C6	0.047 (2)	0.047 (3)	0.045 (2)	−0.008 (2)	0.009 (2)	−0.001 (2)
C7	0.068 (3)	0.053 (3)	0.052 (3)	−0.009 (3)	0.004 (2)	−0.015 (2)
C8	0.075 (3)	0.045 (2)	0.059 (3)	0.000 (2)	0.000 (3)	−0.012 (2)
C9	0.054 (3)	0.040 (2)	0.052 (3)	−0.003 (2)	0.006 (2)	0.001 (2)
C10	0.049 (2)	0.042 (2)	0.041 (2)	−0.005 (2)	0.009 (2)	−0.004 (2)
C11	0.052 (3)	0.044 (2)	0.056 (3)	0.002 (2)	0.004 (2)	0.000 (2)
C12	0.060 (3)	0.050 (3)	0.054 (3)	−0.009 (2)	0.000 (2)	0.000 (2)
C13	0.055 (3)	0.041 (2)	0.049 (2)	−0.005 (2)	0.007 (2)	0.005 (2)
C14	0.060 (3)	0.032 (2)	0.063 (3)	0.002 (2)	0.016 (2)	0.000 (2)
C15	0.058 (3)	0.058 (3)	0.067 (3)	0.003 (2)	0.001 (2)	0.007 (2)
C16	0.111 (4)	0.065 (3)	0.091 (3)	0.029 (3)	−0.024 (3)	0.004 (3)
C17	0.078 (3)	0.099 (3)	0.055 (2)	−0.002 (3)	−0.010 (2)	−0.008 (2)
C18	0.113 (4)	0.078 (3)	0.071 (3)	0.024 (3)	0.020 (3)	0.023 (2)

Geometric parameters (Å, º) top

O1—C11	1.205 (4)	C8—H8	0.9300
O2—C12	1.223 (3)	C9—C10	1.390 (4)
O3—C14	1.347 (3)	C9—C14	1.455 (5)
O3—C16	1.483 (4)	C10—C11	1.485 (4)
C1—C2	1.344 (4)	C11—C12	1.547 (5)
C1—C6	1.434 (4)	C12—C13	1.416 (4)
C1—C17	1.510 (4)	C13—C14	1.335 (4)
C2—C3	1.405 (4)	C13—C15	1.505 (4)
C2—H2	0.9300	C15—C18	1.510 (4)
C3—C4	1.360 (4)	C15—C16	1.533 (4)
C3—H3	0.9300	C15—H15	0.9800
C4—C5	1.410 (4)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C10	1.421 (4)	C17—H17A	0.9600
C5—C6	1.435 (4)	C17—H17B	0.9600
C6—C7	1.401 (4)	C17—H17C	0.9600
C7—C8	1.371 (4)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.386 (4)	C18—H18C	0.9600

C14—O3—C16	107.0 (3)	O2—C12—C13	124.4 (4)
C2—C1—C6	118.9 (4)	O2—C12—C11	118.4 (3)
C2—C1—C17	121.2 (4)	C13—C12—C11	117.2 (4)
C6—C1—C17	119.8 (3)	C14—C13—C12	118.9 (4)
C1—C2—C3	121.2 (4)	C14—C13—C15	110.7 (3)
C1—C2—H2	119.4	C12—C13—C15	130.4 (4)
C3—C2—H2	119.4	C13—C14—O3	114.3 (4)
C4—C3—C2	121.7 (4)	C13—C14—C9	127.4 (4)
C4—C3—H3	119.2	O3—C14—C9	118.3 (4)
C2—C3—H3	119.2	C13—C15—C18	113.4 (3)
C3—C4—C5	120.2 (4)	C13—C15—C16	100.7 (3)
C3—C4—H4	119.9	C18—C15—C16	113.9 (3)
C5—C4—H4	119.9	C13—C15—H15	109.5
C4—C5—C10	123.4 (4)	C18—C15—H15	109.5
C4—C5—C6	117.9 (3)	C16—C15—H15	109.5
C10—C5—C6	118.8 (3)	O3—C16—C15	107.2 (3)
C7—C6—C1	121.0 (4)	O3—C16—H16A	110.3
C7—C6—C5	118.8 (3)	C15—C16—H16A	110.3
C1—C6—C5	120.2 (3)	O3—C16—H16B	110.3
C8—C7—C6	121.8 (4)	C15—C16—H16B	110.3
C8—C7—H7	119.1	H16A—C16—H16B	108.5
C6—C7—H7	119.1	C1—C17—H17A	109.5
C7—C8—C9	119.6 (4)	C1—C17—H17B	109.5
C7—C8—H8	120.2	H17A—C17—H17B	109.5
C9—C8—H8	120.2	C1—C17—H17C	109.5
C8—C9—C10	121.7 (4)	H17A—C17—H17C	109.5
C8—C9—C14	119.7 (4)	H17B—C17—H17C	109.5
C10—C9—C14	118.5 (4)	C15—C18—H18A	109.5
C9—C10—C5	119.3 (3)	C15—C18—H18B	109.5
C9—C10—C11	117.9 (4)	H18A—C18—H18B	109.5
C5—C10—C11	122.8 (3)	C15—C18—H18C	109.5
O1—C11—C10	124.2 (4)	H18A—C18—H18C	109.5
O1—C11—C12	116.1 (3)	H18B—C18—H18C	109.5
C10—C11—C12	119.7 (3)

C6—C1—C2—C3	−1.1 (6)	C5—C10—C11—O1	−4.4 (6)
C17—C1—C2—C3	179.9 (3)	C9—C10—C11—C12	−2.3 (5)
C1—C2—C3—C4	0.0 (6)	C5—C10—C11—C12	177.7 (3)
C2—C3—C4—C5	0.2 (6)	O1—C11—C12—O2	8.4 (5)
C3—C4—C5—C10	−179.7 (3)	C10—C11—C12—O2	−173.6 (3)
C3—C4—C5—C6	0.7 (5)	O1—C11—C12—C13	−171.5 (4)
C2—C1—C6—C7	−177.9 (4)	C10—C11—C12—C13	6.5 (5)
C17—C1—C6—C7	1.1 (5)	O2—C12—C13—C14	173.8 (4)
C2—C1—C6—C5	2.0 (5)	C11—C12—C13—C14	−6.4 (5)
C17—C1—C6—C5	−179.0 (3)	O2—C12—C13—C15	−6.3 (6)
C4—C5—C6—C7	178.1 (3)	C11—C12—C13—C15	173.6 (3)
C10—C5—C6—C7	−1.5 (4)	C12—C13—C14—O3	−179.6 (3)
C4—C5—C6—C1	−1.8 (5)	C15—C13—C14—O3	0.4 (4)
C10—C5—C6—C1	178.6 (3)	C12—C13—C14—C9	2.3 (6)
C1—C6—C7—C8	−179.9 (3)	C15—C13—C14—C9	−177.7 (3)
C5—C6—C7—C8	0.2 (5)	C16—O3—C14—C13	0.8 (4)
C6—C7—C8—C9	0.5 (6)	C16—O3—C14—C9	179.1 (3)
C7—C8—C9—C10	0.1 (5)	C8—C9—C14—C13	−178.3 (4)
C7—C8—C9—C14	−179.4 (3)	C10—C9—C14—C13	2.2 (6)
C8—C9—C10—C5	−1.3 (5)	C8—C9—C14—O3	3.7 (5)
C14—C9—C10—C5	178.1 (3)	C10—C9—C14—O3	−175.8 (3)
C8—C9—C10—C11	178.7 (3)	C14—C13—C15—C18	120.7 (3)
C14—C9—C10—C11	−1.9 (5)	C12—C13—C15—C18	−59.3 (5)
C4—C5—C10—C9	−177.5 (3)	C14—C13—C15—C16	−1.4 (4)
C6—C5—C10—C9	2.0 (4)	C12—C13—C15—C16	178.7 (4)
C4—C5—C10—C11	2.5 (5)	C14—O3—C16—C15	−1.7 (4)
C6—C5—C10—C11	−178.0 (3)	C13—C15—C16—O3	1.8 (4)
C9—C10—C11—O1	175.6 (4)	C18—C15—C16—O3	−120.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1ⁱ	0.96	2.53	3.379 (4)	147
C16—H16A···O2ⁱ	0.97	2.48	3.384 (5)	155
C17—H17A···O2ⁱⁱ	0.96	2.56	3.484 (4)	162
C17—H17C···O2ⁱⁱⁱ	0.96	2.66	3.377 (4)	132
C7—H7···O3^iv	0.93	2.67	3.481 (4)	146

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+5/2, −y+1, z+1/2; (iv) x+1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O₃
M_r	278.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	4.6415 (10), 14.692 (3), 19.633 (4)
V (Å³)	1338.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.977, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	6925, 2502, 1140
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.077, 1.03
No. of reflections	2502
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.26

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1ⁱ	0.96	2.53	3.379 (4)	147.1
C16—H16A···O2ⁱ	0.97	2.48	3.384 (5)	154.8
C17—H17A···O2ⁱⁱ	0.96	2.56	3.484 (4)	162.4
C17—H17C···O2ⁱⁱⁱ	0.96	2.66	3.377 (4)	131.6
C7—H7···O3^iv	0.93	2.67	3.481 (4)	146.1

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+5/2, −y+1, z+1/2; (iv) x+1/2, −y+3/2, −z+2.

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province (No. 092102310075) and the Education Chamber of Henan Province (No. 2008B150013 ), which are gratefully acknowledged.

References

Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chang, H.-M., Chui, K.-Y., Tan, F. W. L., Yang, Y., Zhong, Z.-P., Lee, C.-M., Sham, H.-L. & Wong, H. N. C. (1991). J. Med. Chem. 34, 1675–1692. CrossRef PubMed CAS Web of Science Google Scholar
Ryu, S. Y., Lee, C. O. & Choi, S. U. (1997). Planta Med. 63, 339–342. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xue, M., Cui, Y., Wang, H.-Q., Hu, H.-Y. & Zhang, B.-J. (1999). Pharm. Biomed. Anal. 21, 207–213. Web of Science CrossRef Google Scholar
Yagi, A., Fujimoto, K., Tanonaka, K., Hirai, K. & Takeo, S. (1989). Planta Med. B55, 51–54. CrossRef Google Scholar
Zhang, L., Wang, J.-K., Qu, Y. & Nie, Q. (2005). Acta Cryst. E61, o3582–o3583. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, J.-R. & Luo, H.-W. (2004). J. Chin. Pharm. Univ. 35, 368–370. CAS Google Scholar