17βH-Periplogenin, a cardiac aglycone from the root bark of Periploca sepium Bunge

Zhang, Y.-W.; Bao, Y.-L.; Wu, Y.; Yu, C.-L.; Li, Y.-X.

doi:10.1107/S1600536812018521

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1582-o1583

doi:10.1107/S1600536812018521

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17βH-Periplogenin, a cardiac aglycone from the root bark of Periploca sepium Bunge

Yu-Wei Zhang,^a Yong-Li Bao,^a Yin Wu,^b ^* Chun-Lei Yu ^c and Yu-Xin Li ^a ^*

^aNational Engineering Laboratory for Druggable Gene and Protein Screening, Northeast Normal University, ChangChun 130024, People's Republic of China, ^bInstitute of Genetics and Cytology, Northeast Normal University, ChangChun 130024, People's Republic of China, and ^cResearch Center of Agriculture and Medicine Gene, Engineering of Ministry of Education, Northeast Normal University, ChangChun 130024, People's Republic of China
^*Correspondence e-mail: wuy705@126.com, liyuxin486@126.com

(Received 13 April 2012; accepted 25 April 2012; online 2 May 2012)

The title compound {systematic name: 4-[(3S,5S,8R,9S,10R,13R,14S,17S)-3,5,14-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]furan-2(5H)-one}, C₂₃H₃₄O₅, was isolated from the roots of Periploca sepium Bunge, a famous Chinese traditional herbal medicine. The three six-membered rings adopt chair conformations, the cyclopentane ring displays an approximate envelope conformation (with the C atom bearing the methyl substituent at the flap) and the five-membered lactone ring adopts an essentially planar [maximum deviation of 0.004 (8) Å] conformation. In the crystal, molecules are linked into helical chains along [010] by O—H⋯O hydrogen bonds and weak C—H⋯O interactions. Two intramolecular O—H⋯O hydrogen bonds are also present.

Related literature

For the botanical and medicinal background to Periploca sepium Bunge, see: Li & Liu (2004 ); Yang et al. (2006 ). For the previous preparation and chemical structure determination of the title compound, see: Furuya et al. (1988 ); Kawaguchi et al. (1998 ).

Experimental

Crystal data

C₂₃H₃₄O₅
M_r = 390.50
Monoclinic, P 2₁
a = 7.434 (3) Å
b = 10.554 (4) Å
c = 13.537 (5) Å
β = 103.118 (5)°
V = 1034.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.26 × 0.24 × 0.02 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.978, T_max = 0.998
5262 measured reflections
1927 independent reflections
1097 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.126
S = 1.01
1927 reflections
254 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯O2	0.82	2.06	2.778 (5)	147
O2—H2C⋯O1	0.82	2.05	2.778 (5)	147
O3—H3B⋯O2ⁱ	0.82	2.16	2.977 (5)	175
C11—H11A⋯O5ⁱⁱ	0.97	2.57	3.393 (7)	143
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); 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/S1600536812018521/wn2470sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018521/wn2470Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018521/wn2470Isup3.cml

checkCIF report

Comment top

Periploca sepium Bunge (Asclepiadaceae) is native and widespread in the Loess hilly regions of northwest China (Li and Liu, 2004; Yang et al., 2006). Its root bark, which is officially listed in the Chinese Pharmacopoeia under the name Cortex Periploca (Xiangjiapi in Chinese), has been frequently used to treat rheumatism and strengthen tendons and bones. The title compound, 17βH-periplogenin, which has been previously obtained as a biotransformation product of digitoxigenin (Furuya et al., 1988; Kawaguchi et al., 1998), was isolated from the root bark of Periploca sepium Bunge in our recent investigation. To the best of our knowledge, this is its first isolation from plant material. The isolated compound was identified by NMR spectra, which were compared with the previous report (Furuya et al., 1988).

The crystal structure of 17βH-periplogenin has not yet been reported. In view of this, the crystal structure determination of the title compound was carried out and the results are presented here.

As shown in Fig. 1, the molecule consists of three six-membered rings (A, B and C), one cyclopentane ring (D) and one five-membered lactone ring. Rings A:B, B:C and C:D are cis-, trans- and cis- fused, respectively. The three six-membered rings adopt chair conformations, the cyclopentane ring displays an approximate envelope conformation with C13 as the flap atom, and the five-membered lactone ring adopts a planar conformation.

In the crystal structure, molecules are linked into helical chains along [010] through O3—H3B···O2 hydrogen bonds and C11—H11A···O5 weak interactions (Fig. 2 and Table 1). Two intramolecular O—H···O hydrogen bonds are also present (Table 1).

Related literature top

For the botanical and medicinal background to Periploca sepium Bunge, see: Li & Liu (2004); Yang et al. (2006). For the previous preparation and chemical structure determination of the title compound, see: Furuya et al. (1988); Kawaguchi et al. (1998).

Experimental top

The air-dried and powdered roots of Periploca sepium Bunge (2.0 kg) were extracted with 70% EtOH (3×10 l, 3×2.0 h, 85 °C) under reflux conditions to give a crude extract, which was suspended in H₂O and successively partitioned with CHCl₃, EtOAc and n-butanol. A part of the CHCl₃ fraction (50.0 g) was subjected to CC [SiO₂, 200–300 mesh, CHCl₃/MeOH (100:0, 95:5, 90:10, 80:20, 70:30, 60:40, 50:50 and 0:100(v/v)] to yield 8 fractions: Fr.1–8. Fr.3 was resubjected to CC (SiO₂, 200–300 mesh, gradient of CHCl₃/MeOH) and was further chromatographed on Sephadex LH-20 (CHCl₃/MeOH, 1:1) to give 6 subfractions: SFr. 1–6. SFr. 4 (0.9 g) was then subjected to reverse phase preparative HPLC [Waters preparative HPLC system; XTERRA PREP MS C18 column, 5 µm, 19 mm × 150 mm; sample loading 30 - 60 mg/injection; the column was eluted with CH₃OH/H₂O system (52:48) at a flow rate of 16 ml/min] to provide the title compound (t_R = 4.81 min, 26 mg). ¹H and ¹³C NMR spectroscopic data of this compound were recorded on a Bruker-AV-400 spectrometer, using CD₃OD as solvent and Me₄Si as internal standard. The stereochemistry was established by the X-ray diffraction experiment.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 the title compound, showing displacement ellipsoids at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis, showing [010] chains. Hydrogen bonds are shown as dashed lines.

4-[(3S,5S,8R,9S,10R,13R,14S,17S)-3,5,14-trihydroxy-10,13-dimethyl-hexadecahydro-1H- cyclopenta[a]phenanthren-17-yl]furan-2(5H)-one top

Crystal data top

C₂₃H₃₄O₅	F(000) = 424
M_r = 390.50	D_x = 1.254 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5262 reflections
a = 7.434 (3) Å	θ = 1.5–25.0°
b = 10.554 (4) Å	µ = 0.09 mm⁻¹
c = 13.537 (5) Å	T = 296 K
β = 103.118 (5)°	Block, colourless
V = 1034.4 (6) Å³	0.26 × 0.24 × 0.02 mm
Z = 2

Data collection top

Bruker APEX CCD area-detector diffractometer	1927 independent reflections
Radiation source: fine-focus sealed tube	1097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.978, T_max = 0.998	k = −12→12
5262 measured reflections	l = −16→9

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)] = 0.053	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0536P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1927 reflections	Δρ_max = 0.17 e Å⁻³
254 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (3)

Crystal data top

C₂₃H₃₄O₅	V = 1034.4 (6) Å³
M_r = 390.50	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.434 (3) Å	µ = 0.09 mm⁻¹
b = 10.554 (4) Å	T = 296 K
c = 13.537 (5) Å	0.26 × 0.24 × 0.02 mm
β = 103.118 (5)°

Data collection top

Bruker APEX CCD area-detector diffractometer	1927 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1097 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.998	R_int = 0.077
5262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
1927 reflections	Δρ_min = −0.18 e Å⁻³
254 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	0.3269 (8)	0.6136 (5)	0.1758 (4)	0.0561 (17)
H1A	0.2076	0.5998	0.1916	0.067*
H1B	0.3112	0.6777	0.1231	0.067*
C2	0.4616 (9)	0.6639 (6)	0.2708 (4)	0.0639 (19)
H2A	0.4156	0.7437	0.2908	0.077*
H2B	0.4681	0.6042	0.3260	0.077*
C3	0.6508 (9)	0.6834 (5)	0.2527 (4)	0.0555 (16)
H3A	0.7350	0.7047	0.3174	0.067*
C4	0.7198 (7)	0.5641 (5)	0.2117 (4)	0.0471 (15)
H4A	0.7423	0.5004	0.2647	0.057*
H4B	0.8368	0.5824	0.1944	0.057*
C5	0.5873 (7)	0.5090 (5)	0.1180 (4)	0.0386 (13)
C6	0.6653 (7)	0.3883 (5)	0.0839 (4)	0.0433 (14)
H6A	0.7914	0.4036	0.0785	0.052*
H6B	0.5937	0.3655	0.0170	0.052*
C7	0.6629 (7)	0.2779 (5)	0.1564 (4)	0.0414 (14)
H7A	0.7462	0.2959	0.2212	0.050*
H7B	0.7058	0.2017	0.1290	0.050*
C8	0.4684 (7)	0.2562 (5)	0.1723 (4)	0.0361 (13)
H8A	0.3901	0.2376	0.1053	0.043*
C9	0.3906 (7)	0.3778 (5)	0.2096 (4)	0.0373 (13)
H9A	0.4724	0.4013	0.2745	0.045*
C10	0.3898 (7)	0.4900 (5)	0.1345 (4)	0.0389 (13)
C11	0.1987 (7)	0.3499 (5)	0.2297 (4)	0.0469 (15)
H11A	0.1527	0.4252	0.2570	0.056*
H11B	0.1136	0.3289	0.1663	0.056*
C12	0.2059 (7)	0.2412 (5)	0.3039 (4)	0.0447 (15)
H12A	0.0842	0.2290	0.3171	0.054*
H12B	0.2899	0.2630	0.3675	0.054*
C13	0.2699 (7)	0.1166 (5)	0.2639 (3)	0.0408 (14)
C14	0.4603 (7)	0.1395 (5)	0.2376 (4)	0.0390 (13)
C15	0.5971 (7)	0.1384 (5)	0.3422 (4)	0.0485 (15)
H15A	0.7128	0.0996	0.3371	0.058*
H15B	0.6219	0.2243	0.3673	0.058*
C16	0.5062 (7)	0.0614 (7)	0.4146 (4)	0.069 (2)
H16A	0.5827	−0.0105	0.4421	0.082*
H16B	0.4876	0.1138	0.4703	0.082*
C17	0.3218 (7)	0.0170 (6)	0.3500 (4)	0.0486 (15)
H17A	0.3448	−0.0630	0.3182	0.058*
C18	0.1250 (8)	0.0656 (6)	0.1759 (4)	0.0617 (18)
H18A	0.0945	0.1293	0.1241	0.093*
H18B	0.0163	0.0431	0.1990	0.093*
H18C	0.1723	−0.0080	0.1487	0.093*
C19	0.2521 (7)	0.4643 (6)	0.0324 (4)	0.0511 (16)
H19A	0.2542	0.5339	−0.0129	0.077*
H19B	0.1299	0.4551	0.0438	0.077*
H19C	0.2866	0.3878	0.0030	0.077*
C20	0.1787 (7)	−0.0093 (6)	0.4098 (4)	0.0473 (15)
C22	0.1329 (8)	0.0576 (7)	0.4823 (4)	0.0612 (18)
H22A	0.1868	0.1340	0.5074	0.073*
C23	−0.0140 (9)	−0.0056 (7)	0.5170 (5)	0.0648 (19)
C21	0.0617 (10)	−0.1253 (7)	0.3915 (6)	0.091 (2)
H21A	−0.0109	−0.1279	0.3222	0.110*
H21B	0.1366	−0.2014	0.4048	0.110*
O5	−0.0980 (6)	0.0251 (6)	0.5800 (3)	0.0923 (17)
O1	0.6546 (6)	0.7847 (4)	0.1820 (3)	0.0702 (13)
H1C	0.6349	0.7560	0.1242	0.105*
O2	0.5832 (5)	0.5977 (3)	0.0338 (2)	0.0470 (10)
H2C	0.6038	0.6697	0.0563	0.071*
O3	0.5070 (5)	0.0290 (3)	0.1852 (3)	0.0538 (11)
H3B	0.4851	0.0431	0.1241	0.081*
O4	−0.0578 (6)	−0.1125 (5)	0.4641 (4)	0.0856 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.057 (4)	0.052 (4)	0.067 (4)	0.022 (3)	0.028 (3)	0.015 (4)
C2	0.109 (6)	0.034 (3)	0.056 (4)	0.007 (3)	0.034 (4)	−0.007 (3)
C3	0.085 (5)	0.038 (3)	0.043 (4)	−0.013 (3)	0.013 (3)	0.004 (3)
C4	0.053 (4)	0.042 (4)	0.043 (3)	−0.011 (3)	0.005 (3)	0.006 (3)
C5	0.051 (3)	0.034 (3)	0.035 (3)	0.004 (3)	0.016 (3)	0.005 (3)
C6	0.041 (3)	0.051 (4)	0.042 (4)	0.002 (3)	0.019 (3)	0.006 (3)
C7	0.044 (3)	0.044 (3)	0.039 (3)	0.008 (3)	0.014 (3)	0.012 (3)
C8	0.042 (3)	0.039 (3)	0.029 (3)	0.001 (3)	0.011 (2)	0.002 (3)
C9	0.039 (3)	0.038 (3)	0.036 (3)	0.009 (3)	0.011 (2)	−0.001 (3)
C10	0.045 (3)	0.038 (3)	0.033 (3)	0.013 (3)	0.008 (2)	0.002 (3)
C11	0.052 (4)	0.039 (3)	0.058 (4)	0.008 (3)	0.030 (3)	0.005 (3)
C12	0.047 (4)	0.048 (4)	0.043 (3)	0.000 (3)	0.020 (3)	0.005 (3)
C13	0.045 (3)	0.049 (4)	0.028 (3)	0.000 (3)	0.006 (3)	0.003 (3)
C14	0.048 (3)	0.037 (3)	0.038 (3)	0.005 (3)	0.022 (3)	−0.001 (3)
C15	0.042 (3)	0.058 (4)	0.045 (3)	0.005 (3)	0.011 (3)	0.008 (3)
C16	0.043 (4)	0.099 (5)	0.062 (4)	−0.004 (4)	0.008 (3)	0.031 (4)
C17	0.046 (3)	0.056 (4)	0.046 (3)	0.000 (3)	0.014 (3)	0.010 (3)
C18	0.066 (4)	0.070 (4)	0.046 (3)	−0.020 (4)	0.007 (3)	−0.004 (3)
C19	0.043 (3)	0.067 (4)	0.040 (3)	0.001 (3)	0.003 (3)	0.017 (3)
C20	0.041 (3)	0.053 (4)	0.047 (4)	−0.001 (3)	0.011 (3)	0.012 (3)
C22	0.059 (4)	0.084 (5)	0.045 (3)	−0.020 (4)	0.021 (3)	0.004 (4)
C23	0.053 (4)	0.089 (6)	0.054 (4)	−0.007 (4)	0.017 (3)	0.013 (5)
C21	0.106 (6)	0.074 (5)	0.111 (6)	−0.025 (5)	0.060 (5)	0.006 (5)
O5	0.071 (3)	0.150 (5)	0.060 (3)	−0.008 (3)	0.025 (2)	0.018 (4)
O1	0.116 (4)	0.046 (2)	0.052 (3)	−0.013 (2)	0.025 (3)	0.002 (2)
O2	0.063 (2)	0.043 (2)	0.037 (2)	−0.0012 (19)	0.0163 (18)	0.0047 (19)
O3	0.083 (3)	0.038 (2)	0.051 (2)	0.014 (2)	0.036 (2)	0.003 (2)
O4	0.088 (4)	0.072 (3)	0.107 (4)	−0.024 (3)	0.044 (3)	0.006 (3)

Geometric parameters (Å, º) top

C1—C10	1.533 (7)	C12—H12A	0.9700
C1—C2	1.534 (8)	C12—H12B	0.9700
C1—H1A	0.9700	C13—C18	1.512 (7)
C1—H1B	0.9700	C13—C17	1.552 (7)
C2—C3	1.496 (8)	C13—C14	1.555 (6)
C2—H2A	0.9700	C14—O3	1.448 (6)
C2—H2B	0.9700	C14—C15	1.545 (7)
C3—O1	1.440 (6)	C15—C16	1.542 (7)
C3—C4	1.512 (8)	C15—H15A	0.9700
C3—H3A	0.9800	C15—H15B	0.9700
C4—C5	1.532 (7)	C16—C17	1.523 (7)
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C5—O2	1.469 (6)	C17—C20	1.502 (7)
C5—C6	1.515 (7)	C17—H17A	0.9800
C5—C10	1.548 (7)	C18—H18A	0.9600
C6—C7	1.527 (7)	C18—H18B	0.9600
C6—H6A	0.9700	C18—H18C	0.9600
C6—H6B	0.9700	C19—H19A	0.9600
C7—C8	1.527 (7)	C19—H19B	0.9600
C7—H7A	0.9700	C19—H19C	0.9600
C7—H7B	0.9700	C20—C22	1.315 (7)
C8—C14	1.525 (7)	C20—C21	1.490 (8)
C8—C9	1.539 (6)	C22—C23	1.447 (8)
C8—H8A	0.9800	C22—H22A	0.9300
C9—C11	1.540 (6)	C23—O5	1.210 (7)
C9—C10	1.560 (6)	C23—O4	1.335 (8)
C9—H9A	0.9800	C21—O4	1.474 (8)
C10—C19	1.546 (7)	C21—H21A	0.9700
C11—C12	1.517 (7)	C21—H21B	0.9700
C11—H11A	0.9700	O1—H1C	0.8200
C11—H11B	0.9700	O2—H2C	0.8200
C12—C13	1.538 (7)	O3—H3B	0.8200

C10—C1—C2	113.9 (4)	C11—C12—H12A	109.1
C10—C1—H1A	108.8	C13—C12—H12A	109.1
C2—C1—H1A	108.8	C11—C12—H12B	109.1
C10—C1—H1B	108.8	C13—C12—H12B	109.1
C2—C1—H1B	108.8	H12A—C12—H12B	107.9
H1A—C1—H1B	107.7	C18—C13—C12	111.1 (5)
C3—C2—C1	111.7 (5)	C18—C13—C17	111.2 (4)
C3—C2—H2A	109.3	C12—C13—C17	111.1 (4)
C1—C2—H2A	109.3	C18—C13—C14	113.4 (4)
C3—C2—H2B	109.3	C12—C13—C14	108.6 (4)
C1—C2—H2B	109.3	C17—C13—C14	101.1 (4)
H2A—C2—H2B	107.9	O3—C14—C8	108.7 (3)
O1—C3—C2	111.8 (5)	O3—C14—C15	105.2 (4)
O1—C3—C4	108.3 (4)	C8—C14—C15	115.7 (4)
C2—C3—C4	110.8 (5)	O3—C14—C13	108.6 (4)
O1—C3—H3A	108.6	C8—C14—C13	114.5 (4)
C2—C3—H3A	108.6	C15—C14—C13	103.5 (4)
C4—C3—H3A	108.6	C16—C15—C14	107.1 (4)
C3—C4—C5	114.3 (5)	C16—C15—H15A	110.3
C3—C4—H4A	108.7	C14—C15—H15A	110.3
C5—C4—H4A	108.7	C16—C15—H15B	110.3
C3—C4—H4B	108.7	C14—C15—H15B	110.3
C5—C4—H4B	108.7	H15A—C15—H15B	108.5
H4A—C4—H4B	107.6	C17—C16—C15	105.3 (4)
O2—C5—C6	103.9 (4)	C17—C16—H16A	110.7
O2—C5—C4	107.2 (4)	C15—C16—H16A	110.7
C6—C5—C4	110.6 (4)	C17—C16—H16B	110.7
O2—C5—C10	110.0 (4)	C15—C16—H16B	110.7
C6—C5—C10	112.1 (4)	H16A—C16—H16B	108.8
C4—C5—C10	112.5 (4)	C20—C17—C16	113.7 (4)
C5—C6—C7	112.6 (4)	C20—C17—C13	116.4 (4)
C5—C6—H6A	109.1	C16—C17—C13	105.1 (4)
C7—C6—H6A	109.1	C20—C17—H17A	107.0
C5—C6—H6B	109.1	C16—C17—H17A	107.0
C7—C6—H6B	109.1	C13—C17—H17A	107.0
H6A—C6—H6B	107.8	C13—C18—H18A	109.5
C6—C7—C8	110.8 (4)	C13—C18—H18B	109.5
C6—C7—H7A	109.5	H18A—C18—H18B	109.5
C8—C7—H7A	109.5	C13—C18—H18C	109.5
C6—C7—H7B	109.5	H18A—C18—H18C	109.5
C8—C7—H7B	109.5	H18B—C18—H18C	109.5
H7A—C7—H7B	108.1	C10—C19—H19A	109.5
C14—C8—C7	111.5 (4)	C10—C19—H19B	109.5
C14—C8—C9	114.6 (4)	H19A—C19—H19B	109.5
C7—C8—C9	111.1 (4)	C10—C19—H19C	109.5
C14—C8—H8A	106.4	H19A—C19—H19C	109.5
C7—C8—H8A	106.4	H19B—C19—H19C	109.5
C9—C8—H8A	106.4	C22—C20—C21	109.0 (5)
C8—C9—C11	109.3 (4)	C22—C20—C17	129.6 (6)
C8—C9—C10	111.4 (4)	C21—C20—C17	121.3 (6)
C11—C9—C10	113.2 (4)	C20—C22—C23	109.7 (6)
C8—C9—H9A	107.5	C20—C22—H22A	125.2
C11—C9—H9A	107.5	C23—C22—H22A	125.2
C10—C9—H9A	107.5	O5—C23—O4	120.1 (7)
C1—C10—C19	106.3 (4)	O5—C23—C22	130.8 (8)
C1—C10—C5	108.6 (4)	O4—C23—C22	109.0 (6)
C19—C10—C5	110.6 (4)	O4—C21—C20	103.3 (6)
C1—C10—C9	111.4 (4)	O4—C21—H21A	111.1
C19—C10—C9	110.7 (4)	C20—C21—H21A	111.1
C5—C10—C9	109.2 (4)	O4—C21—H21B	111.1
C12—C11—C9	111.5 (4)	C20—C21—H21B	111.1
C12—C11—H11A	109.3	H21A—C21—H21B	109.1
C9—C11—H11A	109.3	C3—O1—H1C	109.5
C12—C11—H11B	109.3	C5—O2—H2C	109.5
C9—C11—H11B	109.3	C14—O3—H3B	109.5
H11A—C11—H11B	108.0	C23—O4—C21	108.9 (5)
C11—C12—C13	112.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O2	0.82	2.06	2.778 (5)	147
O2—H2C···O1	0.82	2.05	2.778 (5)	147
O3—H3B···O2ⁱ	0.82	2.16	2.977 (5)	175
C11—H11A···O5ⁱⁱ	0.97	2.57	3.393 (7)	143

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

Experimental details

Crystal data
Chemical formula	C₂₃H₃₄O₅
M_r	390.50
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	7.434 (3), 10.554 (4), 13.537 (5)
β (°)	103.118 (5)
V (Å³)	1034.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.24 × 0.02

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.978, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	5262, 1927, 1097
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.126, 1.01
No. of reflections	1927
No. of parameters	254
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), 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
O1—H1C···O2	0.82	2.06	2.778 (5)	146.8
O2—H2C···O1	0.82	2.05	2.778 (5)	147.0
O3—H3B···O2ⁱ	0.82	2.16	2.977 (5)	174.5
C11—H11A···O5ⁱⁱ	0.97	2.57	3.393 (7)	143

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

Acknowledgements

This research was supported by the National Natural Science Foundation of China (Nos. 31170324 and 31070318), the Fundamental Research Funds for the Central Universities, grants from the Jilin Province Science & Technology Committee, China (Nos. 20100911, 20102203, 20110938 and 20110711), as well as the Scientific and Technical Project of the Administration of Traditional Chinese Medicine of Jilin Province (No. 2010pt069).

References

Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Furuya, T., Kawaguchi, K. & Hirotani, M. (1988). Phytochemistry, 27, 2129–2133. CrossRef CAS Google Scholar
Kawaguchi, K., Koike, S., Hirotani, M., Fujihara, M., Furuya, T., Iwata, R. & Morimoto, K. (1998). Phytochemistry, 47, 1261–1265. Web of Science CrossRef CAS PubMed Google Scholar
Li, S. W. & Liu, L. P. (2004). Acta Bot. Boreali-Occidentalia Sin. 24, 275–280. CAS Google Scholar
Sheldrick, G. M. (1996). 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
Yang, C. H., Wang, Y. Y., Zhou, Z. F. & Zhang, G. C. (2006). For. Res. 19, 231–234. Google Scholar

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1582-o1583

doi:10.1107/S1600536812018521

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17βH-Periplogenin, a cardiac aglycone from the root bark of Periploca sepium Bunge

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