8β-Eth­oxy­eremophil-3,7(11)-diene-8α,12;6α,15-diolide

Fei, D.-Q.; Dong, L.-L.; Li, H.-H.; Zhang, Z.-X.

doi:10.1107/S1600536813015729

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1087

https://doi.org/10.1107/S1600536813015729

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8β-Ethoxyeremophil-3,7(11)-diene-8α,12;6α,15-diolide

Dong-Qing Fei,^a ^* Le-Le Dong,^a Hui-Hong Li ^a and Zhan-Xin Zhang ^a

^aSchool of Pharmacy, Lanzhou University, Lanzhou 730000, People's Republic of China
^*Correspondence e-mail: feidq@lzu.edu.cn

(Received 15 May 2013; accepted 5 June 2013; online 12 June 2013)

The title compound, C₁₇H₂₀O₅, an eremophilane sesquiternoid, was isolated from the roots of Ligularia lapathifolia. The molecule contains four fused rings of which the six-membered ring A adopts a half-chair conformation, the six-membered ring B adopts a chair conformation, the five-membered ring C is almost planar (r.m.s. deviation = 0.015 Å) and the five-membered ring D adopts an envelope conformation with the quaternary C atom as the flap. The methyl and the ethoxy groups adopt a syn conformation and the A/B ring junction is cis-fused. No directional intermolecular interactions could be identified in the crystal.

Related literature

For further information on the isolation of the title compound, see Fei et al. (2007 ). For pucking paramaters, see: Cremer & Pople (1975 ); Boeyens (1978 )

Experimental

Crystal data

C₁₇H₂₀O₅
M_r = 304.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.4925 (2) Å
b = 13.0302 (4) Å
c = 14.1381 (9) Å
V = 1564.50 (12) Å³
Z = 4
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 294 K
0.33 × 0.28 × 0.12 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.743, T_max = 1.000
14336 measured reflections
2994 independent reflections
2871 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.103
S = 1.03
2994 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 )
Flack parameter: −0.1 (2)

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablock global. DOI: https://doi.org/10.1107/S1600536813015729/hb7083sup1.cif

checkCIF report

Comment top

The title compound, 8β-ethoxyeremophil-3,7(11)-diene-8α,12(6α,15)-diolide (Fig. 1), was isolated from the roots of Ligularia lapathifolia (Fei et al., 2007). The title compound is composed of four rings, two six-membered and two five-menbered. The six-membered ring A adopt a half-chair conformation, which has pucking paramaters (Cremer & Pople, 1975; Boeyens, 1978) Q = 0.4766 (19) Å, θ = 130.0 (2)°, φ = 133.8 (3)°. The six-membered ring B adopt a chair conformation with pucking paramaters Q = 0.5073 (17) Å, θ = 22.08 (19)°, φ = 205.7 (5)°. The five-membered ring C is almost planar with a mean torsion angle of 1.50 (8)°. The five-membered ring D adopt an envelope conformation. The A/B ring junction is cis-fused (torsion angle C14—C5—C10—H10 = 43°).

Related literature top

For further information on the isolation of the title compound, see Fei et al. (2007). For pucking paramaters, see: Cremer & Pople (1975); Boeyens (1978)

Experimental top

The air-dried roots of L. lapathifolia (3.6 kg) were powdered and extracted with petroleum ether -diethyl ether-acetone (1:1:1) three times successively at room temperature. The combined extracts were concentrated in vacuum to obtain a residue (270 g), which was subjected to silica gel CC and eluted with petroleum ether-acetone (50:1, 20:1, 8:1, 5:1, 2:1, 1:1, 0:1). On the basis of differences in composition indicated by TLC, seven crude fractions (A—G) were obtained. Fraction B was further fractionated on a silica gel column using petroleum ether-acetone (30:1, 10:1, 5:1, 2:1) to give four crude fractions (B1—B4). Fraction B3 was further fractionated on a silica gel column using petroleum ether-acetone (20:1, 8:1, 2:1) to obtain the pure title compound. Colourless blocks were obtained by slow evaporation of a methanol solution at room terperature.

Structure description top

For further information on the isolation of the title compound, see Fei et al. (2007). For pucking paramaters, see: Cremer & Pople (1975); Boeyens (1978)

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level.

8β-Ethoxyeremophil-3,7(11)-diene-8α,12;6α,15-diolide top

Crystal data top

C₁₇H₂₀O₅	D_x = 1.292 Mg m⁻³
M_r = 304.33	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9242 reflections
a = 8.4925 (2) Å	θ = 4.6–70.7°
b = 13.0302 (4) Å	µ = 0.78 mm⁻¹
c = 14.1381 (9) Å	T = 294 K
V = 1564.50 (12) Å³	Block, colourless
Z = 4	0.33 × 0.28 × 0.12 mm
F(000) = 648

Data collection top

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	2994 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2871 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 16.0733 pixels mm^-1	θ_max = 70.8°, θ_min = 4.6°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −15→15
T_min = 0.743, T_max = 1.000	l = −16→17
14336 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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0636P)² + 0.1574P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.003
2994 reflections	Δρ_max = 0.13 e Å⁻³
202 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 000 Friedel pairs
Primary atom site location: iterative	Absolute structure parameter: −0.1 (2)

Crystal data top

C₁₇H₂₀O₅	V = 1564.50 (12) Å³
M_r = 304.33	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.4925 (2) Å	µ = 0.78 mm⁻¹
b = 13.0302 (4) Å	T = 294 K
c = 14.1381 (9) Å	0.33 × 0.28 × 0.12 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	2994 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	2871 reflections with I > 2σ(I)
T_min = 0.743, T_max = 1.000	R_int = 0.027
14336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.103	Δρ_max = 0.13 e Å⁻³
S = 1.03	Δρ_min = −0.18 e Å⁻³
2994 reflections	Absolute structure: Flack (1983), 000 Friedel pairs
202 parameters	Absolute structure parameter: −0.1 (2)
0 restraints

Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.9183 (2)	0.64050 (12)	0.11330 (10)	0.0794 (4)
O2	0.79269 (15)	0.60175 (8)	0.24732 (9)	0.0556 (3)
O3	0.82873 (14)	0.24550 (10)	0.20230 (9)	0.0580 (3)
O4	0.6780 (2)	0.17448 (13)	0.09057 (11)	0.0839 (5)
O5	0.81102 (14)	0.52062 (10)	0.39285 (7)	0.0514 (3)
C1	0.3694 (2)	0.36787 (16)	0.35509 (16)	0.0642 (5)
H1A	0.3487	0.3085	0.3945	0.077*
H1B	0.3133	0.4257	0.3822	0.077*
C2	0.3051 (2)	0.34733 (16)	0.25617 (17)	0.0678 (5)
H2A	0.2071	0.3096	0.2617	0.081*
H2B	0.2818	0.4124	0.2260	0.081*
C3	0.4146 (2)	0.28847 (14)	0.19487 (14)	0.0582 (4)
H3	0.3795	0.2650	0.1365	0.070*
C4	0.5619 (2)	0.26851 (12)	0.22151 (12)	0.0484 (4)
C5	0.63488 (19)	0.29910 (12)	0.31377 (12)	0.0467 (4)
C6	0.80727 (18)	0.31837 (12)	0.27873 (11)	0.0457 (4)
H6	0.8817	0.3034	0.3299	0.055*
C7	0.83272 (17)	0.42502 (11)	0.24365 (11)	0.0416 (3)
C8	0.75684 (19)	0.50977 (12)	0.30066 (11)	0.0436 (3)
C9	0.58186 (19)	0.49238 (12)	0.30652 (12)	0.0460 (4)
H9A	0.5376	0.4907	0.2433	0.055*
H9B	0.5331	0.5486	0.3407	0.055*
C10	0.5468 (2)	0.39090 (12)	0.35713 (12)	0.0481 (4)
H10	0.5794	0.3977	0.4233	0.058*
C11	0.89795 (19)	0.46356 (14)	0.16573 (11)	0.0485 (4)
C12	0.8750 (2)	0.57663 (15)	0.16860 (12)	0.0551 (4)
C13	0.9784 (2)	0.4157 (2)	0.08268 (13)	0.0680 (5)
H13A	1.0069	0.3463	0.0978	0.102*
H13B	1.0715	0.4541	0.0676	0.102*
H13C	0.9085	0.4159	0.0293	0.102*
C14	0.6368 (3)	0.20772 (17)	0.38296 (16)	0.0726 (6)
H14A	0.6874	0.2279	0.4408	0.109*
H14B	0.6935	0.1516	0.3551	0.109*
H14C	0.5307	0.1867	0.3961	0.109*
C15	0.6863 (2)	0.22373 (14)	0.16241 (14)	0.0575 (4)
C16	0.9771 (2)	0.5300 (2)	0.40545 (14)	0.0762 (7)
H16A	1.0163	0.5873	0.3686	0.091*
H16B	1.0290	0.4681	0.3835	0.091*
C17	1.0122 (3)	0.5461 (3)	0.50483 (17)	0.0970 (9)
H17A	1.1237	0.5406	0.5148	0.146*
H17B	0.9588	0.4953	0.5420	0.146*
H17C	0.9773	0.6133	0.5234	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0966 (11)	0.0798 (10)	0.0619 (8)	−0.0179 (9)	0.0110 (8)	0.0133 (8)
O2	0.0652 (7)	0.0444 (6)	0.0572 (7)	−0.0037 (5)	0.0106 (6)	−0.0012 (5)
O3	0.0483 (6)	0.0539 (6)	0.0718 (7)	0.0118 (5)	−0.0004 (6)	−0.0224 (6)
O4	0.0807 (10)	0.0882 (11)	0.0828 (10)	−0.0103 (9)	0.0044 (8)	−0.0454 (9)
O5	0.0490 (6)	0.0629 (7)	0.0422 (6)	−0.0064 (5)	0.0061 (5)	−0.0128 (5)
C1	0.0469 (9)	0.0657 (12)	0.0800 (13)	−0.0003 (9)	0.0186 (9)	0.0034 (10)
C2	0.0406 (8)	0.0616 (10)	0.1014 (15)	−0.0028 (8)	0.0023 (10)	0.0036 (11)
C3	0.0480 (9)	0.0559 (9)	0.0707 (11)	−0.0084 (7)	−0.0062 (8)	−0.0015 (9)
C4	0.0457 (8)	0.0414 (8)	0.0580 (9)	−0.0049 (6)	−0.0002 (7)	−0.0044 (7)
C5	0.0457 (8)	0.0435 (8)	0.0510 (9)	0.0038 (6)	0.0009 (7)	0.0012 (7)
C6	0.0404 (7)	0.0469 (8)	0.0497 (8)	0.0094 (6)	−0.0042 (7)	−0.0087 (7)
C7	0.0349 (7)	0.0486 (8)	0.0412 (7)	0.0026 (6)	−0.0023 (6)	−0.0095 (6)
C8	0.0452 (8)	0.0428 (8)	0.0427 (8)	−0.0009 (6)	0.0051 (6)	−0.0042 (6)
C9	0.0431 (8)	0.0442 (8)	0.0508 (8)	0.0066 (6)	0.0069 (7)	−0.0044 (7)
C10	0.0462 (8)	0.0507 (9)	0.0474 (8)	0.0020 (7)	0.0096 (7)	−0.0004 (7)
C11	0.0405 (8)	0.0662 (10)	0.0387 (8)	0.0000 (7)	0.0016 (6)	−0.0077 (7)
C12	0.0544 (10)	0.0647 (10)	0.0462 (9)	−0.0088 (8)	0.0015 (7)	0.0037 (8)
C13	0.0609 (11)	0.0976 (15)	0.0454 (9)	0.0077 (11)	0.0106 (8)	−0.0129 (10)
C14	0.0833 (14)	0.0608 (12)	0.0738 (12)	0.0049 (10)	0.0043 (11)	0.0214 (10)
C15	0.0575 (10)	0.0494 (9)	0.0655 (10)	−0.0025 (8)	−0.0012 (9)	−0.0146 (8)
C16	0.0539 (11)	0.1208 (19)	0.0537 (11)	−0.0224 (12)	0.0009 (9)	−0.0185 (12)
C17	0.0844 (17)	0.147 (3)	0.0600 (13)	−0.0186 (16)	−0.0166 (11)	−0.0009 (15)

Geometric parameters (Å, º) top

O1—C12	1.200 (2)	C6—C7	1.491 (2)
O2—C8	1.4484 (19)	C7—C8	1.511 (2)
O2—C12	1.354 (2)	C7—C11	1.331 (2)
O3—C6	1.4501 (18)	C8—C9	1.506 (2)
O3—C15	1.364 (2)	C9—H9A	0.9700
O4—C15	1.204 (2)	C9—H9B	0.9700
O5—C8	1.3894 (19)	C9—C10	1.533 (2)
O5—C16	1.427 (2)	C10—H10	0.9800
C1—H1A	0.9700	C11—C12	1.487 (3)
C1—H1B	0.9700	C11—C13	1.495 (2)
C1—C2	1.525 (3)	C13—H13A	0.9600
C1—C10	1.536 (2)	C13—H13B	0.9600
C2—H2A	0.9700	C13—H13C	0.9600
C2—H2B	0.9700	C14—H14A	0.9600
C2—C3	1.485 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C3—C4	1.332 (3)	C16—H16A	0.9700
C4—C5	1.498 (2)	C16—H16B	0.9700
C4—C15	1.468 (3)	C16—C17	1.452 (3)
C5—C6	1.566 (2)	C17—H17A	0.9600
C5—C10	1.538 (2)	C17—H17B	0.9600
C5—C14	1.541 (2)	C17—H17C	0.9600
C6—H6	0.9800

C12—O2—C8	109.65 (12)	C8—C9—C10	110.33 (13)
C15—O3—C6	109.44 (12)	H9A—C9—H9B	108.1
C8—O5—C16	116.95 (13)	C10—C9—H9A	109.6
H1A—C1—H1B	107.7	C10—C9—H9B	109.6
C2—C1—H1A	108.8	C1—C10—C5	108.51 (14)
C2—C1—H1B	108.8	C1—C10—H10	108.2
C2—C1—C10	113.74 (15)	C5—C10—H10	108.2
C10—C1—H1A	108.8	C9—C10—C1	110.51 (14)
C10—C1—H1B	108.8	C9—C10—C5	112.97 (13)
C1—C2—H2A	108.8	C9—C10—H10	108.2
C1—C2—H2B	108.8	C7—C11—C12	107.26 (14)
H2A—C2—H2B	107.7	C7—C11—C13	133.06 (18)
C3—C2—C1	113.69 (16)	C12—C11—C13	119.65 (17)
C3—C2—H2A	108.8	O1—C12—O2	121.74 (18)
C3—C2—H2B	108.8	O1—C12—C11	129.02 (18)
C2—C3—H3	119.2	O2—C12—C11	109.25 (14)
C4—C3—C2	121.60 (18)	C11—C13—H13A	109.5
C4—C3—H3	119.2	C11—C13—H13B	109.5
C3—C4—C5	125.64 (16)	C11—C13—H13C	109.5
C3—C4—C15	126.34 (18)	H13A—C13—H13B	109.5
C15—C4—C5	107.69 (15)	H13A—C13—H13C	109.5
C4—C5—C6	98.85 (13)	H13B—C13—H13C	109.5
C4—C5—C10	110.65 (14)	C5—C14—H14A	109.5
C4—C5—C14	110.58 (15)	C5—C14—H14B	109.5
C10—C5—C6	117.14 (13)	C5—C14—H14C	109.5
C10—C5—C14	110.67 (15)	H14A—C14—H14B	109.5
C14—C5—C6	108.35 (14)	H14A—C14—H14C	109.5
O3—C6—C5	104.38 (13)	H14B—C14—H14C	109.5
O3—C6—H6	109.7	O3—C15—C4	108.67 (14)
O3—C6—C7	110.13 (12)	O4—C15—O3	120.78 (18)
C5—C6—H6	109.7	O4—C15—C4	130.56 (19)
C7—C6—C5	112.97 (12)	O5—C16—H16A	109.7
C7—C6—H6	109.7	O5—C16—H16B	109.7
C6—C7—C8	116.21 (13)	O5—C16—C17	109.64 (19)
C11—C7—C6	133.40 (14)	H16A—C16—H16B	108.2
C11—C7—C8	110.06 (14)	C17—C16—H16A	109.7
O2—C8—C7	103.73 (12)	C17—C16—H16B	109.7
O2—C8—C9	111.14 (14)	C16—C17—H17A	109.5
O5—C8—O2	109.54 (13)	C16—C17—H17B	109.5
O5—C8—C7	115.69 (14)	C16—C17—H17C	109.5
O5—C8—C9	106.89 (13)	H17A—C17—H17B	109.5
C9—C8—C7	109.89 (13)	H17A—C17—H17C	109.5
C8—C9—H9A	109.6	H17B—C17—H17C	109.5
C8—C9—H9B	109.6

O2—C8—C9—C10	176.04 (12)	C7—C11—C12—O1	178.38 (19)
O3—C6—C7—C8	157.37 (13)	C7—C11—C12—O2	−1.6 (2)
O3—C6—C7—C11	−15.2 (2)	C8—O2—C12—O1	−179.84 (17)
O5—C8—C9—C10	−64.47 (16)	C8—O2—C12—C11	0.15 (19)
C1—C2—C3—C4	−8.3 (3)	C8—O5—C16—C17	176.9 (2)
C2—C1—C10—C5	−58.3 (2)	C8—C7—C11—C12	2.34 (18)
C2—C1—C10—C9	66.0 (2)	C8—C7—C11—C13	−175.70 (18)
C2—C3—C4—C5	1.3 (3)	C8—C9—C10—C1	−174.70 (14)
C2—C3—C4—C15	−171.17 (17)	C8—C9—C10—C5	−52.92 (19)
C3—C4—C5—C6	−146.24 (17)	C10—C1—C2—C3	37.6 (2)
C3—C4—C5—C10	−22.7 (2)	C10—C5—C6—O3	−151.01 (14)
C3—C4—C5—C14	100.3 (2)	C10—C5—C6—C7	−31.4 (2)
C3—C4—C15—O3	160.45 (17)	C11—C7—C8—O2	−2.24 (17)
C3—C4—C15—O4	−20.1 (3)	C11—C7—C8—O5	−122.21 (15)
C4—C5—C6—O3	−32.27 (14)	C11—C7—C8—C9	116.66 (15)
C4—C5—C6—C7	87.37 (15)	C12—O2—C8—O5	125.24 (14)
C4—C5—C10—C1	48.68 (18)	C12—O2—C8—C7	1.17 (17)
C4—C5—C10—C9	−74.22 (17)	C12—O2—C8—C9	−116.86 (15)
C5—C4—C15—O3	−13.11 (19)	C13—C11—C12—O1	−3.3 (3)
C5—C4—C15—O4	166.4 (2)	C13—C11—C12—O2	176.75 (15)
C5—C6—C7—C8	41.10 (18)	C14—C5—C6—O3	82.97 (16)
C5—C6—C7—C11	−131.49 (18)	C14—C5—C6—C7	−157.39 (14)
C6—O3—C15—O4	171.11 (18)	C14—C5—C10—C1	−74.25 (19)
C6—O3—C15—C4	−9.36 (19)	C14—C5—C10—C9	162.84 (15)
C6—C5—C10—C1	160.89 (15)	C15—O3—C6—C5	26.98 (17)
C6—C5—C10—C9	38.0 (2)	C15—O3—C6—C7	−94.55 (16)
C6—C7—C8—O2	−176.51 (13)	C15—C4—C5—C6	27.38 (16)
C6—C7—C8—O5	63.51 (18)	C15—C4—C5—C10	150.88 (14)
C6—C7—C8—C9	−57.62 (18)	C15—C4—C5—C14	−86.13 (17)
C6—C7—C11—C12	175.26 (16)	C16—O5—C8—O2	−64.2 (2)
C6—C7—C11—C13	−2.8 (3)	C16—O5—C8—C7	52.5 (2)
C7—C8—C9—C10	61.80 (17)	C16—O5—C8—C9	175.24 (17)

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀O₅
M_r	304.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	8.4925 (2), 13.0302 (4), 14.1381 (9)
V (Å³)	1564.50 (12)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.33 × 0.28 × 0.12

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Eos)
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.743, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14336, 2994, 2871
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.103, 1.03
No. of reflections	2994
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18
Absolute structure	Flack (1983), 000 Friedel pairs
Absolute structure parameter	−0.1 (2)

Computer programs: CrysAlis PRO (Agilent, 2013), SUPERFLIP (Palatinus & Chapuis, 2007), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

We are grateful to the National Natural Science Foundation of China (No. 21102065), the Natural Science Foundation of Gansu Province, China (No. 1208RJYA029) and the Fundational Research Funds for the Central Universities (Nos. lzujbky-2012–83 and lzujbky-2013–72) for financial support of this research.

References

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