Crystal structure of 4α-hy­droxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate

Lu, Q.-Q.; Shi, X.-W.; Yang, X.-K.

doi:10.1107/S2056989015011251

organic compounds

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Volume 71| Part 7| July 2015| Page o518

doi:10.1107/S2056989015011251

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Crystal structure of 4α-hydroxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate

Qiang-Qiang Lu,^a Xin-Wei Shi ^a ^* and Xing-Ke Yang ^b

^aXi'an Botanical Garden, Institute of Botany of Shaanxi Province, Xi'an 710061, People's Republic of China, and ^bShaanxi Province Academy of Sciences, Xi'an 710061, People's Republic of China
^*Correspondence e-mail: sxw@ms.xab.ac.cn

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 30 May 2015; accepted 9 June 2015; online 27 June 2015)

The title compound, C₁₅H₂₂O₃·H₂O, is a natural producr isolated from Chloranthus japonicus, which is a eudesmane sesquiterpenoid. The two trans-fused six-membered rings have chair confomations. In the crystal, O—H⋯O hydrogen bonds link the components into corrugated layers parallel to the bc plane. There are C—H⋯O interactions present within and between the layers.

Keywords: crystal structure; eudesmane sesquiterpenoid; hydrogen bonds; Chloranthus japonicus.

CCDC reference: 1405865

1. Related literature

For the products isolated from the genus Chloranthus, see: Xiao et al. (2010 ); Sun et al. (2012 ). For the crystal structure of the related compound 6β-hydroxyeremophil-7(11)-en-8β,12-olide, see: Su et al. (2011 ).

2. Experimental

2.1. Crystal data

C₁₅H₂₂O₃·H₂O
M_r = 268.34
Monoclinic, P 2₁
a = 10.2495 (2) Å
b = 7.1061 (1) Å
c = 10.5275 (2) Å
β = 100.026 (1)°
V = 755.05 (2) Å³
Z = 2
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 298 K
0.40 × 0.40 × 0.30 mm

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.772, T_max = 0.821
3081 measured reflections
1339 independent reflections
1303 reflections with I > 2σ(I)
R_int = 0.018

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.130
S = 1.14
1339 reflections
174 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4ⁱ	0.98	2.63	3.407 (3)	136
C8—H8⋯O3ⁱⁱ	0.98	2.64	3.308 (4)	126
O1—H1⋯O4ⁱ	0.82	1.91	2.718 (3)	169
O4—H4WA⋯O3ⁱⁱ	0.83	2.05	2.850 (3)	162
O4—H4WB⋯O1ⁱⁱⁱ	0.86	1.94	2.764 (3)	159
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: ORTEP (Johnson & Burnett, 1996 ).

Supporting information

CCDC reference: 1405865

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015011251/cv5488sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011251/cv5488Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011251/cv5488Isup4.cdx

checkCIF report

Comment top

Chloranthus japonicus (Chloranthaceae,"yin-xian-cao"in chinese) is mainly distributed in the east of Asia and traditionally used as Chinese herbal medicine in the treatment of fractures, carbuncles, trauma, and rheumatism. In our current phytochemical investigation, the title compound - an eudesmane sesquiterpenoid, was isolated from the whole plant of C. japonicus for the first time.The compound was identified by NMR spectroscopic data, which were also elucidated by comparing with the literature data (Xiao et al., 2010). Herein, we report its crystal structure.

The main molecule of the title compound consists of a fused three-ring system (Fig.1). The two methyl groups attached to C4 and C10 and the H atom at C8 are all in the axial position and assigned β-configuration, whereas, the hydroxy group at C4 site has α-orientation.

In the crystal, intermolecular O—H···O hydrogen bonds (Table 1, Fig. 2) link all moeties into corrugated layers parallel to bc plane, and weak C—H···O interactions (Table 1) consolidate further the crystal packing.

Experimental top

The title compound was isolated from the whole plant of C. japonicus following the known procedure (Xiao et al., 2010).

Refinement top

The hydrogen atoms were placed in calculated positions and refined as riding with U_iso(H) =1.2 U_eq (C) or 1.5 U_eq(C, O). The positions of methyl and hydroxy hydrogens were rotationally optimized.

Related literature top

For the products isolated from the genus Chloranthus, see: Xiao et al. (2010); Sun et al. (2012). For the crystal structure of the related compound 6β-hydroxyeremophil-7(11)-en-8β,12-olide, see: Su et al. (2011).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: ORTEP (Johnson & Burnett, 1996).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atomic numbering and 40% probability displacement ellipsoids.
	Fig. 2. A portion of the crystal packing showing O—H···O hydrogen bonds as dashed lines.

4α-Hydroxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate top

Crystal data top

C₁₅H₂₂O₃·H₂O	F(000) = 292
M_r = 268.34	D_x = 1.180 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 2390 reflections
a = 10.2495 (2) Å	θ = 4.3–66.9°
b = 7.1061 (1) Å	µ = 0.68 mm⁻¹
c = 10.5275 (2) Å	T = 298 K
β = 100.026 (1)°	Block, colourless
V = 755.05 (2) Å³	0.40 × 0.40 × 0.30 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1339 independent reflections
Radiation source: fine-focus sealed tube	1303 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
phi and ω scans	θ_max = 64.0°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
T_min = 0.772, T_max = 0.821	k = −6→8
3081 measured reflections	l = −11→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.092P)² + 0.043P] where P = (F_o² + 2F_c²)/3
1339 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₅H₂₂O₃·H₂O	V = 755.05 (2) Å³
M_r = 268.34	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 10.2495 (2) Å	µ = 0.68 mm⁻¹
b = 7.1061 (1) Å	T = 298 K
c = 10.5275 (2) Å	0.40 × 0.40 × 0.30 mm
β = 100.026 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1339 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1303 reflections with I > 2σ(I)
T_min = 0.772, T_max = 0.821	R_int = 0.018
3081 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.130	H-atom parameters constrained
S = 1.18	Δρ_max = 0.22 e Å⁻³
1339 reflections	Δρ_min = −0.34 e Å⁻³
174 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
C1	0.0506 (3)	−0.0853 (6)	0.6719 (3)	0.0694 (9)
H1A	−0.0282	−0.0510	0.6111	0.083*
H1B	0.0885	−0.1959	0.6384	0.083*
C2	0.0108 (3)	−0.1346 (10)	0.7998 (3)	0.0938 (16)
H2A	−0.0511	−0.2391	0.7881	0.113*
H2B	−0.0331	−0.0277	0.8313	0.113*
C3	0.1333 (3)	−0.1883 (7)	0.8991 (3)	0.0795 (12)
H3A	0.1061	−0.2173	0.9807	0.095*
H3B	0.1732	−0.3005	0.8700	0.095*
C4	0.2366 (3)	−0.0303 (5)	0.9198 (2)	0.0545 (7)
C5	0.2709 (2)	0.0271 (3)	0.7882 (2)	0.0400 (5)
H5	0.3093	−0.0863	0.7567	0.048*
C6	0.3814 (2)	0.1752 (4)	0.7989 (2)	0.0482 (6)
H6A	0.3501	0.2943	0.8272	0.058*
H6B	0.4571	0.1352	0.8616	0.058*
C7	0.4201 (2)	0.1974 (3)	0.6697 (2)	0.0438 (5)
C8	0.3125 (3)	0.2269 (4)	0.5558 (2)	0.0493 (6)
H8	0.2754	0.3536	0.5590	0.059*
C9	0.2037 (2)	0.0820 (4)	0.5517 (2)	0.0468 (6)
H9A	0.2377	−0.0411	0.5347	0.056*
H9B	0.1317	0.1120	0.4820	0.056*
C10	0.1512 (2)	0.0772 (4)	0.6805 (2)	0.0480 (6)
C11	0.5357 (2)	0.1772 (4)	0.6310 (2)	0.0469 (6)
C12	0.5101 (3)	0.1860 (4)	0.4896 (3)	0.0507 (6)
C13	0.6713 (3)	0.1422 (6)	0.7066 (3)	0.0659 (8)
H13A	0.6695	0.1563	0.7970	0.099*
H13B	0.7324	0.2312	0.6812	0.099*
H13C	0.6990	0.0169	0.6901	0.099*
C14	0.0832 (4)	0.2651 (6)	0.7002 (4)	0.0763 (10)
H14A	0.0210	0.2956	0.6237	0.114*
H14B	0.1487	0.3627	0.7171	0.114*
H14C	0.0373	0.2545	0.7720	0.114*
C15	0.1959 (3)	0.1322 (8)	0.9998 (3)	0.0838 (13)
H15A	0.1939	0.0893	1.0859	0.126*
H15B	0.1096	0.1764	0.9613	0.126*
H15C	0.2588	0.2329	1.0025	0.126*
O1	0.35464 (17)	−0.1021 (3)	0.99853 (14)	0.0547 (5)
H1	0.3829	−0.1911	0.9619	0.082*
O2	0.37912 (19)	0.2109 (3)	0.44542 (16)	0.0572 (5)
O3	0.5884 (2)	0.1702 (4)	0.41479 (17)	0.0635 (6)
O4	0.4640 (3)	0.6381 (4)	0.85924 (19)	0.0861 (8)
H4WA	0.4612	0.6284	0.7803	0.103*
H4WB	0.5174	0.5467	0.8853	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0398 (13)	0.106 (3)	0.0599 (16)	−0.0191 (17)	0.0010 (11)	0.0081 (18)
C2	0.0463 (14)	0.165 (5)	0.0689 (19)	−0.033 (2)	0.0068 (13)	0.020 (3)
C3	0.0572 (17)	0.123 (3)	0.0595 (16)	−0.025 (2)	0.0128 (13)	0.025 (2)
C4	0.0433 (13)	0.0820 (19)	0.0394 (12)	0.0026 (13)	0.0106 (9)	0.0026 (14)
C5	0.0330 (11)	0.0499 (13)	0.0371 (11)	0.0018 (9)	0.0065 (8)	−0.0020 (9)
C6	0.0447 (12)	0.0580 (14)	0.0414 (11)	−0.0076 (12)	0.0057 (9)	−0.0093 (12)
C7	0.0467 (12)	0.0426 (12)	0.0412 (11)	−0.0065 (10)	0.0054 (9)	−0.0028 (10)
C8	0.0525 (13)	0.0519 (13)	0.0432 (12)	0.0018 (11)	0.0072 (10)	0.0079 (11)
C9	0.0416 (12)	0.0578 (14)	0.0384 (11)	0.0031 (11)	−0.0006 (9)	0.0050 (11)
C10	0.0352 (11)	0.0638 (15)	0.0433 (12)	0.0049 (12)	0.0022 (9)	0.0014 (12)
C11	0.0474 (12)	0.0495 (13)	0.0441 (12)	−0.0106 (11)	0.0090 (9)	−0.0033 (11)
C12	0.0594 (14)	0.0468 (13)	0.0481 (12)	−0.0101 (12)	0.0152 (10)	0.0021 (12)
C13	0.0443 (13)	0.094 (2)	0.0591 (15)	−0.0076 (16)	0.0085 (11)	−0.0161 (17)
C14	0.0619 (18)	0.095 (3)	0.0706 (19)	0.0369 (19)	0.0087 (14)	0.0012 (18)
C15	0.0711 (19)	0.135 (4)	0.0500 (15)	0.036 (2)	0.0229 (13)	−0.010 (2)
O1	0.0528 (10)	0.0745 (13)	0.0355 (8)	0.0038 (9)	0.0039 (7)	0.0017 (8)
O2	0.0614 (11)	0.0679 (12)	0.0431 (9)	−0.0022 (10)	0.0112 (7)	0.0131 (9)
O3	0.0697 (12)	0.0720 (13)	0.0536 (10)	−0.0126 (11)	0.0248 (9)	0.0002 (11)
O4	0.1200 (19)	0.0856 (18)	0.0479 (10)	0.0426 (17)	0.0013 (11)	−0.0041 (11)

Geometric parameters (Å, º) top

C1—C2	1.515 (4)	C8—C9	1.512 (4)
C1—C10	1.541 (4)	C8—H8	0.9800
C1—H1A	0.9700	C9—C10	1.545 (3)
C1—H1B	0.9700	C9—H9A	0.9700
C2—C3	1.536 (5)	C9—H9B	0.9700
C2—H2A	0.9700	C10—C14	1.537 (4)
C2—H2B	0.9700	C11—C12	1.468 (4)
C3—C4	1.532 (5)	C11—C13	1.497 (4)
C3—H3A	0.9700	C12—O3	1.223 (3)
C3—H3B	0.9700	C12—O2	1.354 (4)
C4—O1	1.436 (3)	C13—H13A	0.9600
C4—C15	1.530 (5)	C13—H13B	0.9600
C4—C5	1.542 (3)	C13—H13C	0.9600
C5—C6	1.536 (3)	C14—H14A	0.9600
C5—C10	1.559 (3)	C14—H14B	0.9600
C5—H5	0.9800	C14—H14C	0.9600
C6—C7	1.490 (3)	C15—H15A	0.9600
C6—H6A	0.9700	C15—H15B	0.9600
C6—H6B	0.9700	C15—H15C	0.9600
C7—C11	1.325 (3)	O1—H1	0.8200
C7—C8	1.496 (3)	O4—H4WA	0.8291
C8—O2	1.451 (3)	O4—H4WB	0.8628

C2—C1—C10	113.7 (3)	O2—C8—H8	109.8
C2—C1—H1A	108.8	C7—C8—H8	109.8
C10—C1—H1A	108.8	C9—C8—H8	109.8
C2—C1—H1B	108.8	C8—C9—C10	110.9 (2)
C10—C1—H1B	108.8	C8—C9—H9A	109.5
H1A—C1—H1B	107.7	C10—C9—H9A	109.5
C1—C2—C3	110.4 (2)	C8—C9—H9B	109.5
C1—C2—H2A	109.6	C10—C9—H9B	109.5
C3—C2—H2A	109.6	H9A—C9—H9B	108.0
C1—C2—H2B	109.6	C14—C10—C1	110.2 (2)
C3—C2—H2B	109.6	C14—C10—C9	109.5 (2)
H2A—C2—H2B	108.1	C1—C10—C9	107.3 (2)
C4—C3—C2	112.2 (4)	C14—C10—C5	114.7 (2)
C4—C3—H3A	109.2	C1—C10—C5	107.8 (2)
C2—C3—H3A	109.2	C9—C10—C5	107.04 (18)
C4—C3—H3B	109.2	C7—C11—C12	107.2 (2)
C2—C3—H3B	109.2	C7—C11—C13	130.6 (2)
H3A—C3—H3B	107.9	C12—C11—C13	122.1 (2)
O1—C4—C15	103.5 (2)	O3—C12—O2	120.9 (3)
O1—C4—C3	108.3 (3)	O3—C12—C11	128.9 (3)
C15—C4—C3	112.5 (3)	O2—C12—C11	110.2 (2)
O1—C4—C5	108.18 (19)	C11—C13—H13A	109.4
C15—C4—C5	114.9 (3)	C11—C13—H13B	109.4
C3—C4—C5	109.1 (2)	H13A—C13—H13B	109.5
C6—C5—C4	113.3 (2)	C11—C13—H13C	109.5
C6—C5—C10	112.0 (2)	H13A—C13—H13C	109.5
C4—C5—C10	116.10 (19)	H13B—C13—H13C	109.5
C6—C5—H5	104.7	C10—C14—H14A	109.5
C4—C5—H5	104.7	C10—C14—H14B	109.5
C10—C5—H5	104.7	H14A—C14—H14B	109.5
C7—C6—C5	108.42 (18)	C10—C14—H14C	109.5
C7—C6—H6A	110.0	H14A—C14—H14C	109.5
C5—C6—H6A	110.0	H14B—C14—H14C	109.5
C7—C6—H6B	110.0	C4—C15—H15A	109.5
C5—C6—H6B	110.0	C4—C15—H15B	109.5
H6A—C6—H6B	108.4	H15A—C15—H15B	109.5
C11—C7—C6	131.6 (2)	C4—C15—H15C	109.5
C11—C7—C8	110.0 (2)	H15A—C15—H15C	109.5
C6—C7—C8	118.0 (2)	H15B—C15—H15C	109.5
O2—C8—C7	104.3 (2)	C4—O1—H1	109.5
O2—C8—C9	111.8 (2)	C12—O2—C8	108.18 (19)
C7—C8—C9	111.4 (2)	H4WA—O4—H4WB	99.5

C10—C1—C2—C3	−58.1 (6)	C2—C1—C10—C5	53.2 (4)
C1—C2—C3—C4	57.9 (5)	C8—C9—C10—C14	65.4 (3)
C2—C3—C4—O1	−171.6 (3)	C8—C9—C10—C1	−175.0 (2)
C2—C3—C4—C15	74.7 (3)	C8—C9—C10—C5	−59.5 (3)
C2—C3—C4—C5	−54.1 (4)	C6—C5—C10—C14	−60.4 (3)
O1—C4—C5—C6	−58.2 (3)	C4—C5—C10—C14	71.8 (3)
C15—C4—C5—C6	56.8 (3)	C6—C5—C10—C1	176.4 (2)
C3—C4—C5—C6	−175.8 (2)	C4—C5—C10—C1	−51.3 (3)
O1—C4—C5—C10	170.1 (2)	C6—C5—C10—C9	61.3 (3)
C15—C4—C5—C10	−74.9 (3)	C4—C5—C10—C9	−166.4 (2)
C3—C4—C5—C10	52.6 (3)	C6—C7—C11—C12	170.7 (3)
C4—C5—C6—C7	171.3 (2)	C8—C7—C11—C12	−1.8 (3)
C10—C5—C6—C7	−55.0 (3)	C6—C7—C11—C13	−6.6 (5)
C5—C6—C7—C11	−122.4 (3)	C8—C7—C11—C13	−179.0 (3)
C5—C6—C7—C8	49.6 (3)	C7—C11—C12—O3	−178.5 (3)
C11—C7—C8—O2	3.0 (3)	C13—C11—C12—O3	−1.0 (5)
C6—C7—C8—O2	−170.6 (2)	C7—C11—C12—O2	−0.1 (3)
C11—C7—C8—C9	123.7 (2)	C13—C11—C12—O2	177.4 (3)
C6—C7—C8—C9	−49.9 (3)	O3—C12—O2—C8	−179.4 (3)
O2—C8—C9—C10	169.80 (19)	C11—C12—O2—C8	2.1 (3)
C7—C8—C9—C10	53.6 (3)	C7—C8—O2—C12	−3.0 (3)
C2—C1—C10—C14	−72.7 (4)	C9—C8—O2—C12	−123.5 (2)
C2—C1—C10—C9	168.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.98	2.63	3.407 (3)	136
C8—H8···O3ⁱⁱ	0.98	2.64	3.308 (4)	126
O1—H1···O4ⁱ	0.82	1.91	2.718 (3)	169
O4—H4WA···O3ⁱⁱ	0.83	2.05	2.850 (3)	162
O4—H4WB···O1ⁱⁱⁱ	0.86	1.94	2.764 (3)	159

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.98	2.63	3.407 (3)	136.3
C8—H8···O3ⁱⁱ	0.98	2.64	3.308 (4)	125.9
O1—H1···O4ⁱ	0.82	1.91	2.718 (3)	169.0
O4—H4WA···O3ⁱⁱ	0.83	2.05	2.850 (3)	162.0
O4—H4WB···O1ⁱⁱⁱ	0.86	1.94	2.764 (3)	158.7

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 31200257), The Overall Science and Technology Innovation program of Shaanxi Province (grant No. 2012 KTCL02–07) and the West Light Foundation of The Chinese Academy of Sciences (grant No. 2012DF05).

References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Johnson, C. K. & Burnett, M. N. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Su, R.-N., Shi, S., Wu, H.-B. & Wang, W.-S. (2011). Acta Cryst. E67, o1361. CSD CrossRef IUCr Journals Google Scholar
Sun, C.-L., Yan, H., Li, X.-H., Zheng, X.-F. & Liu, H.-Y. (2012). Nat. Prod. Bioprospect. 2, 156–159. CrossRef CAS Google Scholar
Xiao, Z.-Y., Wang, X.-C., Zhang, G.-P., Huang, Z.-L. & Hu, L.-H. (2010). Helv. Chim. Acta, 93, 803–810. CrossRef CAS Google Scholar

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Volume 71| Part 7| July 2015| Page o518

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4α-hy­dr­oxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4α-hydroxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate