Menthyl 2-oxo-2H-chromene-3-carboxyl­ate

Xu, C.-L.; Liu, S.-Y.; Chen, G.; Yang, G.-Y.; Zhao, M.-Q.

doi:10.1107/S1600536809035995

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2431

doi:10.1107/S1600536809035995

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Menthyl 2-oxo-2H-chromene-3-carboxylate

Cui-Lian Xu,^a ^* Shan-Yu Liu,^b Gang Chen,^a Guo-Yu Yang ^a and Ming-Qin Zhao ^b

^aCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China, and ^bCollege of Tobacco Science, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: xucuilian666@126.com

(Received 16 August 2009; accepted 6 September 2009; online 12 September 2009)

The title compound, C₂₀H₂₄O₄, was synthesized from the reaction of 2-oxo-2H-chromene-3-acyl chloride and menthol. The mean plane of the ester group and that of the four essentially planar (maximum deviation 0.0112 Å) C atoms of the chair-form cyclohexyl ring form dihedral angles of 43.8 (3) ° and 81.8 (1)°, respectively, with the mean plane of the coumarin ring system. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds connect the molecules into a two-dimensional network.

Related literature

For the applications of coumarin compounds, see: Yu et al. (2003 , 2007 ).

Experimental

Crystal data

C₂₀H₂₄O₄
M_r = 328.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.080 (2) Å
b = 12.408 (3) Å
c = 13.532 (3) Å
V = 1860.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 K
0.18 × 0.18 × 0.17 mm

Data collection

Rigaku R-AXIS-IV diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi,1995 ) T_min = 0.986, T_max = 0.986
5812 measured reflections
1943 independent reflections
1654 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.138
S = 1.09
1943 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2ⁱ	0.93	2.43	3.288 (5)	154
C5—H5A⋯O3ⁱⁱ	0.93	2.42	3.276 (5)	152
Symmetry codes: (i) $[-x+{\script{5\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: R-AXIS (Rigaku, 1997 ); cell refinement: R-AXIS data reduction: R-AXIS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: TEXSAN (Molecular Structure Corporation & Rigaku (2000 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: TEXSAN.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035995/lh2883sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035995/lh2883Isup2.hkl

checkCIF report

Comment top

Coumarins are a type of plant-derived compounds, which are of interest mainly because of their excellent bioactivities in many areas (Yu et al., 2003; Yu et al., 2007). Some coumarin derivatives have shown to be potential anti-HIV agents, antibiotics, and antioxidants. We have synthesized the title compound (I) and its crystal structure is reported herein.

The molecular structure of (I) is shown in Fig. 1. The compound is composed of a coumarin core with a menthyloxycarbonyl in 3-position. The dihedral angle between the plane of ester group and the plane of coumarin ring system is 43.8 (3)°. The dihedral angle between the coumarin ring system and the plane defined by four essentially planar carbon atoms (C11/C13/C14/C16) of the chair form cyclohexyl ring is 81.8 (1)°. In the crystal structure, weak intermolecular C—H···O hydrogen bonds connect molecules into a two-dimensional network (Fig. 2).

Related literature top

For the applications of coumarin compounds, see: Yu et al. (2003); Yu et al. (2007).

Experimental top

A solution of menthol (0.0072 mol) dissolved in dried methyl dichloride (DCM) (25ml) was added dropwise to a solution of 2-oxo-2H-chromene -3-acyl chloride (0.0072 mol) dissolved in DCM (25 ml) and triethylamine (1 ml) at room temperature. The reaction mixture was stirred for 24 h (mornitored by TLC). The mixture was then neutralized with 5% HCl and washed with saturated NaHCO₃ and brine respectively. The organic phase was dried over Na₂SO₄ and evaporated under the reduced pressure. The resulting residue was purified by column chromatography (EtOAc: petroleum ether) to give the pure compound. Single crystals of the title compound suitable for X-ray diffractions were obtained by slow evaporation of a mixed solvent (ethyl acetate: petroleum ether = 1:1, 10 ml) solution of the title compound (0.035 g).

Computing details top

Data collection: R-AXIS (Rigaku, 1997); cell refinement: R-AXIS (Rigaku, 1997); data reduction: R-AXIS (Rigaku, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: TEXSAN (Molecular Structure Corporation & Rigaku (2000) and PLATON (Spek, 2009); software used to prepare material for publication: TEXSAN (Molecular Structure Corporation & Rigaku (2000).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of the title compound showing weak C– H···O hydrogen bonds as dashed lines. Only H atoms involved in H– bonding have been shown.

Menthyl 2-oxo-2H-chromene-3-carboxylate top

Crystal data top

C₂₀H₂₄O₄	F(000) = 704
M_r = 328.39	D_x = 1.173 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 489 reflections
a = 11.080 (2) Å	θ = 2.2–25.5°
b = 12.408 (3) Å	µ = 0.08 mm⁻¹
c = 13.532 (3) Å	T = 291 K
V = 1860.3 (6) Å³	Prism, colorless
Z = 4	0.18 × 0.18 × 0.17 mm

Data collection top

Rigaku R-AXIS-IV diffractometer	1943 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
Detector resolution: 0 pixels mm^-1	θ_max = 25.5°, θ_min = 2.2°
Oscillation frames scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi,1995)	k = 0→15
T_min = 0.986, T_max = 0.986	l = −16→16
5812 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0742P)² + 0.172P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1943 reflections	Δρ_max = 0.15 e Å⁻³
218 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (5)

Crystal data top

C₂₀H₂₄O₄	V = 1860.3 (6) Å³
M_r = 328.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.080 (2) Å	µ = 0.08 mm⁻¹
b = 12.408 (3) Å	T = 291 K
c = 13.532 (3) Å	0.18 × 0.18 × 0.17 mm

Data collection top

Rigaku R-AXIS-IV diffractometer	1943 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi,1995)	1654 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.986	R_int = 0.063
5812 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.09	Δρ_max = 0.15 e Å⁻³
1943 reflections	Δρ_min = −0.17 e Å⁻³
218 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	1.1789 (2)	1.01848 (18)	0.10921 (18)	0.0682 (7)
O2	1.0992 (3)	1.1284 (2)	0.2180 (2)	0.0863 (8)
O3	0.9734 (2)	1.0101 (2)	0.37733 (18)	0.0852 (8)
O4	0.83141 (18)	0.92908 (18)	0.28562 (15)	0.0591 (6)
C1	1.1825 (3)	0.9219 (3)	0.0601 (2)	0.0593 (8)
C2	1.2617 (3)	0.9135 (3)	−0.0176 (3)	0.0814 (11)
H2A	1.3124	0.9706	−0.0337	0.098*
C3	1.2651 (4)	0.8204 (4)	−0.0710 (3)	0.0929 (13)
H3A	1.3179	0.8145	−0.1242	0.111*
C4	1.1909 (5)	0.7341 (4)	−0.0468 (3)	0.0931 (14)
H4A	1.1947	0.6707	−0.0833	0.112*
C5	1.1114 (4)	0.7426 (3)	0.0315 (3)	0.0760 (10)
H5A	1.0618	0.6849	0.0478	0.091*
C6	1.1055 (3)	0.8379 (2)	0.0861 (2)	0.0545 (7)
C7	1.0247 (3)	0.8555 (2)	0.1674 (2)	0.0547 (7)
H7A	0.9738	0.8000	0.1873	0.066*
C8	1.0208 (3)	0.9499 (2)	0.2151 (2)	0.0508 (7)
C9	1.0994 (3)	1.0387 (3)	0.1849 (2)	0.0611 (8)
C10	0.9412 (3)	0.9684 (3)	0.3017 (2)	0.0571 (8)
C11	0.7426 (3)	0.9362 (2)	0.3663 (2)	0.0565 (8)
H11A	0.7545	1.0039	0.4022	0.068*
C12	0.6189 (3)	0.9375 (3)	0.3173 (2)	0.0656 (9)
H12A	0.6123	0.8708	0.2789	0.079*
C13	0.5222 (3)	0.9316 (3)	0.3989 (3)	0.0834 (11)
H13A	0.5242	0.9976	0.4373	0.100*
H13B	0.4431	0.9261	0.3685	0.100*
C14	0.5413 (4)	0.8365 (3)	0.4669 (3)	0.0853 (12)
H14A	0.4794	0.8369	0.5175	0.102*
H14B	0.5327	0.7704	0.4293	0.102*
C15	0.6634 (4)	0.8376 (3)	0.5156 (3)	0.0755 (10)
H15A	0.6690	0.9033	0.5555	0.091*
C16	0.7619 (3)	0.8429 (3)	0.4359 (3)	0.0668 (9)
H16A	0.8401	0.8502	0.4675	0.080*
H16B	0.7620	0.7761	0.3986	0.080*
C17	0.5998 (4)	1.0313 (4)	0.2444 (3)	0.0888 (12)
H17A	0.6684	1.0305	0.1987	0.107*
C18	0.4854 (5)	1.0146 (6)	0.1819 (4)	0.142 (2)
H18A	0.4882	0.9450	0.1511	0.213*
H18B	0.4811	1.0694	0.1320	0.213*
H18C	0.4156	1.0190	0.2237	0.213*
C19	0.5982 (5)	1.1416 (4)	0.2928 (4)	0.1272 (19)
H19A	0.5862	1.1959	0.2432	0.191*
H19B	0.6737	1.1539	0.3257	0.191*
H19C	0.5336	1.1447	0.3400	0.191*
C20	0.6831 (6)	0.7415 (4)	0.5839 (4)	0.1226 (19)
H20A	0.6209	0.7401	0.6332	0.184*
H20B	0.7604	0.7479	0.6154	0.184*
H20C	0.6805	0.6761	0.5461	0.184*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0560 (13)	0.0657 (14)	0.0828 (15)	−0.0095 (11)	0.0147 (13)	0.0056 (12)
O2	0.103 (2)	0.0614 (14)	0.0946 (18)	−0.0128 (13)	0.0082 (17)	−0.0075 (14)
O3	0.0623 (15)	0.122 (2)	0.0708 (15)	−0.0146 (15)	0.0000 (13)	−0.0310 (15)
O4	0.0420 (11)	0.0798 (14)	0.0556 (12)	−0.0051 (10)	0.0088 (10)	−0.0100 (11)
C1	0.0418 (16)	0.073 (2)	0.0635 (19)	0.0067 (15)	0.0045 (15)	0.0122 (17)
C2	0.060 (2)	0.097 (3)	0.087 (3)	0.012 (2)	0.026 (2)	0.012 (2)
C3	0.070 (2)	0.125 (3)	0.084 (3)	0.028 (3)	0.032 (2)	0.011 (3)
C4	0.095 (3)	0.103 (3)	0.081 (3)	0.029 (3)	0.011 (3)	−0.019 (2)
C5	0.083 (3)	0.070 (2)	0.075 (2)	0.008 (2)	0.010 (2)	−0.0050 (19)
C6	0.0466 (16)	0.0606 (17)	0.0564 (17)	0.0036 (14)	0.0032 (15)	0.0057 (15)
C7	0.0450 (16)	0.0618 (17)	0.0572 (16)	−0.0066 (14)	−0.0003 (15)	0.0057 (14)
C8	0.0407 (15)	0.0583 (17)	0.0533 (15)	−0.0003 (13)	−0.0028 (14)	0.0008 (14)
C9	0.0510 (18)	0.064 (2)	0.069 (2)	−0.0023 (15)	−0.0058 (16)	0.0037 (17)
C10	0.0445 (17)	0.0688 (19)	0.0579 (18)	0.0017 (15)	−0.0032 (15)	−0.0072 (16)
C11	0.0494 (17)	0.0660 (18)	0.0541 (17)	0.0028 (14)	0.0092 (15)	−0.0053 (15)
C12	0.0461 (17)	0.083 (2)	0.068 (2)	0.0034 (17)	0.0045 (16)	−0.0060 (18)
C13	0.0520 (19)	0.105 (3)	0.093 (3)	0.001 (2)	0.016 (2)	−0.008 (2)
C14	0.075 (3)	0.095 (3)	0.086 (3)	−0.019 (2)	0.036 (2)	−0.015 (2)
C15	0.082 (3)	0.079 (2)	0.066 (2)	−0.004 (2)	0.020 (2)	−0.0009 (19)
C16	0.063 (2)	0.074 (2)	0.0637 (19)	0.0068 (17)	0.0091 (17)	0.0003 (18)
C17	0.062 (2)	0.113 (3)	0.091 (3)	0.016 (2)	−0.002 (2)	0.019 (2)
C18	0.107 (4)	0.188 (6)	0.130 (4)	0.018 (4)	−0.044 (4)	0.027 (4)
C19	0.134 (4)	0.099 (3)	0.149 (4)	0.025 (3)	−0.001 (4)	0.023 (4)
C20	0.148 (5)	0.121 (4)	0.099 (3)	0.001 (4)	0.038 (4)	0.033 (3)

Geometric parameters (Å, º) top

O1—C1	1.370 (4)	C12—C13	1.540 (5)
O1—C9	1.374 (4)	C12—H12A	0.9800
O2—C9	1.199 (4)	C13—C14	1.512 (6)
O3—C10	1.201 (4)	C13—H13A	0.9700
O4—C10	1.328 (4)	C13—H13B	0.9700
O4—C11	1.472 (4)	C14—C15	1.504 (6)
C1—C2	1.374 (5)	C14—H14A	0.9700
C1—C6	1.392 (4)	C14—H14B	0.9700
C2—C3	1.363 (6)	C15—C20	1.525 (6)
C2—H2A	0.9300	C15—C16	1.535 (5)
C3—C4	1.389 (6)	C15—H15A	0.9800
C3—H3A	0.9300	C16—H16A	0.9700
C4—C5	1.382 (5)	C16—H16B	0.9700
C4—H4A	0.9300	C17—C19	1.517 (7)
C5—C6	1.396 (5)	C17—C18	1.537 (7)
C5—H5A	0.9300	C17—H17A	0.9800
C6—C7	1.434 (4)	C18—H18A	0.9600
C7—C8	1.338 (4)	C18—H18B	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.463 (4)	C19—H19A	0.9600
C8—C10	1.485 (4)	C19—H19B	0.9600
C11—C16	1.508 (5)	C19—H19C	0.9600
C11—C12	1.522 (4)	C20—H20A	0.9600
C11—H11A	0.9800	C20—H20B	0.9600
C12—C17	1.539 (5)	C20—H20C	0.9600

C1—O1—C9	122.7 (2)	C12—C13—H13A	109.2
C10—O4—C11	117.9 (2)	C14—C13—H13B	109.2
O1—C1—C2	117.1 (3)	C12—C13—H13B	109.2
O1—C1—C6	120.9 (3)	H13A—C13—H13B	107.9
C2—C1—C6	121.9 (3)	C15—C14—C13	112.6 (3)
C3—C2—C1	119.2 (4)	C15—C14—H14A	109.1
C3—C2—H2A	120.4	C13—C14—H14A	109.1
C1—C2—H2A	120.4	C15—C14—H14B	109.1
C2—C3—C4	120.8 (4)	C13—C14—H14B	109.1
C2—C3—H3A	119.6	H14A—C14—H14B	107.8
C4—C3—H3A	119.6	C14—C15—C20	112.8 (4)
C5—C4—C3	119.9 (4)	C14—C15—C16	109.4 (3)
C5—C4—H4A	120.1	C20—C15—C16	110.9 (4)
C3—C4—H4A	120.1	C14—C15—H15A	107.9
C4—C5—C6	120.1 (4)	C20—C15—H15A	107.9
C4—C5—H5A	120.0	C16—C15—H15A	107.9
C6—C5—H5A	120.0	C11—C16—C15	111.7 (3)
C1—C6—C5	118.1 (3)	C11—C16—H16A	109.3
C1—C6—C7	117.6 (3)	C15—C16—H16A	109.3
C5—C6—C7	124.3 (3)	C11—C16—H16B	109.3
C8—C7—C6	121.5 (3)	C15—C16—H16B	109.3
C8—C7—H7A	119.2	H16A—C16—H16B	107.9
C6—C7—H7A	119.2	C19—C17—C18	110.4 (4)
C7—C8—C9	120.4 (3)	C19—C17—C12	114.0 (4)
C7—C8—C10	122.4 (3)	C18—C17—C12	111.3 (4)
C9—C8—C10	117.2 (3)	C19—C17—H17A	106.9
O2—C9—O1	116.6 (3)	C18—C17—H17A	106.9
O2—C9—C8	126.4 (3)	C12—C17—H17A	106.9
O1—C9—C8	116.9 (3)	C17—C18—H18A	109.5
O3—C10—O4	124.8 (3)	C17—C18—H18B	109.5
O3—C10—C8	124.3 (3)	H18A—C18—H18B	109.5
O4—C10—C8	110.9 (3)	C17—C18—H18C	109.5
O4—C11—C16	108.8 (2)	H18A—C18—H18C	109.5
O4—C11—C12	106.2 (2)	H18B—C18—H18C	109.5
C16—C11—C12	114.1 (3)	C17—C19—H19A	109.5
O4—C11—H11A	109.2	C17—C19—H19B	109.5
C16—C11—H11A	109.2	H19A—C19—H19B	109.5
C12—C11—H11A	109.2	C17—C19—H19C	109.5
C11—C12—C17	114.3 (3)	H19A—C19—H19C	109.5
C11—C12—C13	108.3 (3)	H19B—C19—H19C	109.5
C17—C12—C13	113.6 (3)	C15—C20—H20A	109.5
C11—C12—H12A	106.7	C15—C20—H20B	109.5
C17—C12—H12A	106.7	H20A—C20—H20B	109.5
C13—C12—H12A	106.7	C15—C20—H20C	109.5
C14—C13—C12	112.1 (3)	H20A—C20—H20C	109.5
C14—C13—H13A	109.2	H20B—C20—H20C	109.5

C9—O1—C1—C2	176.7 (3)	C11—O4—C10—C8	177.2 (2)
C9—O1—C1—C6	−1.0 (4)	C7—C8—C10—O3	133.2 (4)
O1—C1—C2—C3	−177.6 (3)	C9—C8—C10—O3	−44.8 (5)
C6—C1—C2—C3	0.1 (5)	C7—C8—C10—O4	−44.5 (4)
C1—C2—C3—C4	−0.8 (6)	C9—C8—C10—O4	137.5 (3)
C2—C3—C4—C5	0.7 (7)	C10—O4—C11—C16	−83.0 (3)
C3—C4—C5—C6	0.1 (6)	C10—O4—C11—C12	153.7 (3)
O1—C1—C6—C5	178.3 (3)	O4—C11—C12—C17	−58.8 (4)
C2—C1—C6—C5	0.7 (5)	C16—C11—C12—C17	−178.7 (3)
O1—C1—C6—C7	−1.3 (4)	O4—C11—C12—C13	173.5 (3)
C2—C1—C6—C7	−178.9 (3)	C16—C11—C12—C13	53.6 (4)
C4—C5—C6—C1	−0.8 (5)	C11—C12—C13—C14	−53.9 (4)
C4—C5—C6—C7	178.8 (3)	C17—C12—C13—C14	178.0 (3)
C1—C6—C7—C8	1.6 (4)	C12—C13—C14—C15	57.7 (4)
C5—C6—C7—C8	−178.0 (3)	C13—C14—C15—C20	−179.8 (3)
C6—C7—C8—C9	0.3 (4)	C13—C14—C15—C16	−55.8 (4)
C6—C7—C8—C10	−177.6 (3)	O4—C11—C16—C15	−173.5 (3)
C1—O1—C9—O2	−175.3 (3)	C12—C11—C16—C15	−55.1 (4)
C1—O1—C9—C8	2.9 (4)	C14—C15—C16—C11	53.8 (4)
C7—C8—C9—O2	175.4 (3)	C20—C15—C16—C11	178.8 (4)
C10—C8—C9—O2	−6.6 (5)	C11—C12—C17—C19	−66.3 (5)
C7—C8—C9—O1	−2.5 (4)	C13—C12—C17—C19	58.5 (5)
C10—C8—C9—O1	175.5 (2)	C11—C12—C17—C18	167.9 (4)
C11—O4—C10—O3	−0.5 (5)	C13—C12—C17—C18	−67.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.93	2.43	3.288 (5)	154
C5—H5A···O3ⁱⁱ	0.93	2.42	3.276 (5)	152

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄O₄
M_r	328.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	291
a, b, c (Å)	11.080 (2), 12.408 (3), 13.532 (3)
V (Å³)	1860.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.18 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS-IV diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi,1995)
T_min, T_max	0.986, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	5812, 1943, 1654
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.138, 1.09
No. of reflections	1943
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: R-AXIS (Rigaku, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), TEXSAN (Molecular Structure Corporation & Rigaku (2000) and PLATON (Spek, 2009), TEXSAN (Molecular Structure Corporation & Rigaku (2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.93	2.43	3.288 (5)	154
C5—H5A···O3ⁱⁱ	0.93	2.42	3.276 (5)	152

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

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province (No. 2009 A150012).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Molecular Structure Corporation & Rigaku (2000). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1997). R-AXIS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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