De-acetyl-cinobufalactam monohydrate.
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Journal: 2014/June - Acta crystallographica. Section E, Structure reports online
ISSN: 1600-5368
Abstract:
The title compound, C24H33NO4·H2O, the reaction product of de-acetyl-cinobufagin with ammonium acetate, consists of three cyclo-hexane rings (A, B and C), one five-membered ring (D), one six-membered lactone ring (E) and an epoxide ring (F). The stereochemistry of the ring junctures are A/B cis, B/C trans, C/D cis and D/F cis. Cyclo-hexane rings A, B and C have normal chair conformations. The five-membered ring D adopts an envelope conformation (with the C atom bearing the lactone ring as the flap) and the lactone ring E is planar. In the crystal, hy-droxy and water O-H⋯O and amine N-H⋯O hydrogen bonds involving carbonyl, hy-droxy and water O-atom acceptors link the mol-ecules into a three-dimensional network.
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Acta Crystallographica Section E: Structure Reports Online. May/31/2014; 70(Pt 6): o651-o652
Published online May/9/2014
PMID: 24940236
PMC: 4051091
Science Direct: S1600536814010046

De­acetyl­cinobufalactam monohydrate

Abstract

The title compound, C24H33NO4·H2O, the reaction product of de­acetyl­cinobufagin with ammonium acetate, consists of three cyclo­hexane rings (A, B and C), one five-membered ring (D), one six-membered lactone ring (E) and an epoxide ring (F). The stereochemistry of the ring junctures are A/B cis, B/C trans, C/D cis and D/F cis. Cyclo­hexane rings A, B and C have normal chair conformations. The five-membered ring D adopts an envelope conformation (with the C atom bearing the lactone ring as the flap) and the lactone ring E is planar. In the crystal, hy­droxy and water O—H⋯O and amine N—H⋯O hydrogen bonds involving carbonyl, hy­droxy and water O-atom acceptors link the mol­ecules into a three-dimensional network.

Related literature

For a previous isolation of de­acetyl­cinobufagin [cinobufagin systematic name: (3β,5β,15β,16β)-16-acet­oxy-3-hy­droxy-14,15-ep­oxy­bufa-20,22-dienolide] see: Li et al. (2007 ▶). For the biosynthesis of de­acetyl­cinobufagin, see: Zhan et al. (2003 ▶). For its pharmacological activity, see: Yu et al. (2008 ▶); Tian et al. (2013 ▶). For the stereochemistry of bufalin, see: Rohrer et al. (1982 ▶).

Experimental

Crystal data

  • C24H33NO4·H2O

  • Mr = 417.53

  • Monoclinic,

  • a = 8.0097 (2) Å

  • b = 12.1155 (4) Å

  • c = 11.3627 (3) Å

  • β = 95.077 (3)°

  • V = 1098.33 (5) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.71 mm−1

  • T = 290 K

  • 0.40 × 0.32 × 0.10 mm

Data collection

  • Oxford Diffraction Gemini-S Ultra sapphire CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) Tmin = 0.806, Tmax = 1.0

  • 3289 measured reflections
  • 2396 independent reflections

  • 2261 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.08

  • 2396 reflections
  • 280 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814010046/zs2298sup1.cif

e-70-0o651-sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010046/zs2298Isup2.hkl

e-70-0o651-Isup2.hkl

CCDC reference: 1000729

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1
Hydrogen-bond geometry (Å, °)
D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1W—H1WA⋯O4i0.93 (4)1.79 (4)2.710 (3)170 (4)
O1W—H1WB⋯O30.80 (5)2.07 (5)2.867 (3)170 (4)
N1—H1A⋯O1ii0.862.002.839 (3)165
O1—H1B⋯O1Wiii0.821.902.690 (3)161
O3—H3A⋯O1iv0.822.092.868 (2)157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

supplementary crystallographic information

1. Comment

Deacetylcinobufagin is a natural cardiactonic steroid which has beenisolated from the skin of the toad (Li et al., 2007) and hasalsobeen biosynthesized by microbial transformation of cinobufagin (Zhan etal., 2003). Compounds of this type have shown strong cytotoxiceffectsagainst a wide range of cancer cells (Yu et al., 2008). Howevertheyalso possess cardiac toxicity due to the inhibition of sodium-potassiumATPase (Tian et al., 2013). Thus structural modification of thepharmacological profile of the molecule was warranted. Recently we treateddeacetylcinobufagin (isolated in our laboratory) with ammonium acetate, anda new hydrated derivative, C24H33O4N . H2O, the title compound,named deacetylcinobufalactam, was obtained after recrystallization frommethanol at room temperature. We report herein the crystal structure of thiscompound.

The molecule of the title compound (Fig. 1) consists of three cyclohexanerings (A, B and C), one five-membered ring (D),one six-membered lactam ring (E) and an epoxide ring (F). Thestereochemistry of the ring juncture is A/Bcis, B/Ctrans, C/Dcis and D/Fcis. Thecyclohexane rings A, B and C have normal chairconformations. The five-membered ring (D adopts an envelopeconformationwith C17 displaced by -0.381 (3) Å from the mean plane of the remainingfour atoms (C13, C14, C15 and C16). The lactam ring (E) and theepoxide ring (F) are planar and roughly perpendicular to each otherwith a dihedral angle of 96.6 (4)°. Theabsolute configuration determined for bufalin (Rohrer et al.,1982),a similar cardiactonic steroid, was invoked, giving the assignments of the10 chiral centres in the title molecule as shown in Fig. 1.

In the crystal, intermolecular hydroxyl and water O—H···O hydrogen bonds tohydroxyl, carbonyl and water O-atom acceptors and a hetero-amineN—H···Ohydroxyl hydrogen bond (Table 1) link the molecules into athree-dimensional network structure (Figure 2).

2. Experimental

Deacetylcinobufagin (40.0 mg) was dissolved in DMF, then ammonium acetate (38.5 mg) was added under nitrogen protection. The mixture was stirred for threehours at 100 °C. After completion of the reaction, the mixture was poured intowater and extracted with ethyl acetate. The ethyl acetate extract was washedwith water to remove the solvent DMF and the excess ammonium acetate andcondensed by rotary evaporation under reduced pressure. The residue wasrecrystallized in methanol at room temperature to afford colorless crystals(28.6 mg, yield 71.7%).

3. Refinement

The C-bound H atoms were positioned geometrically and were included in therefinement in the riding-model approximation, with C—H = 0.96 Å (CH3)and Uiso(H) = 1.5Ueq(C); 0.97 Å (CH2) andUiso(H) = 1.2Ueq(C); 0.98 Å (CH) and Uiso(H) =1.2Ueq(C); 0.93 Å (aryl H) and Uiso(H)=1.2Ueq(C); O—H = 0.82 Å and Uiso(H) =1.5Ueq(O). The Friedel pair coverage for the collection is low. Itmay be due to an inadequate collection strategy. Recollection of diffractiondata was not thought to be necessary since the absolute configuration can beunambiguously assigned with reference to the known configuration of the closelyrelated compound bufalin (Rohrer et al., 1982)[(C3S,C5R,C8R,C9S,C10S,C13R,C14S,C15R,C16R,C17R) for the 10 chiral centres in the title compound usingthe arbitrarily named atoms employed]. The Flack parameter was refined to0.0 (3) for 571 Friedel pairs. There are 32 reflections missing betweenθ(min) and θ(max), which might be also due to the inadequatecollection strategy, and adjustment of the orientation to tilt the crystalaxis might be helpful for collecting a complete set of diffraction data.In addition, both hydrogen atoms on the water molecule are involved inhydrogen bonding. The O—H bond distances are significantly different fromthe ideal bond length so these two hydrogen atoms were refined freely.The highest residual electron density was 0.142 eÅ3 and has no particularstructural significance.

Figures

Fig. 1.
The molecular structure of the title compound showing atom the numbering scheme and 30% probability displacement ellipsoids. The inter-species hydrogen bond is shown as a dashed line.
Fig. 2.
The packing diagram showing the intermolecular O—H···O and N—H···O hydrogen bonds which are represented by dashed lines. Selected H-atoms highlighting the hydrogen bonding are shown.

Crystal data

C24H33NO4·H2OF(000) = 452
Mr = 417.53Dx = 1.263 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ybCell parameters from 2374 reflections
a = 8.0097 (2) Åθ = 3.9–62.8°
b = 12.1155 (4) ŵ = 0.71 mm−1
c = 11.3627 (3) ÅT = 290 K
β = 95.077 (3)°Plate, colorless
V = 1098.33 (5) Å30.40 × 0.32 × 0.10 mm
Z = 2

Data collection

Oxford Diffraction Gemini-S Ultra sapphire CCD diffractometer2396 independent reflections
Radiation source: fine-focus sealed tube2261 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 62.8°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)h = −9→8
Tmin = 0.806, Tmax = 1.0k = −8→13
3289 measured reflectionsl = −11→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0421P)2 + 0.128P] where P = (Fo2 + 2Fc2)/3
2396 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.14 e Å−3
1 restraintΔρmin = −0.13 e Å−3

Special details

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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-factorwR and goodness of fit S are based on F2, conventionalR-factors R are based on F, with F set to zero fornegative 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 largeas those based on F, and R- factors based on ALL data will beeven larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N1−0.2500 (2)0.63824 (18)0.52081 (16)0.0396 (5)
H1A−0.32960.67200.55200.048*
O10.5226 (2)0.78557 (15)−0.38275 (14)0.0450 (4)
H1B0.57280.8339−0.41590.067*
O20.2223 (2)0.53707 (14)0.21889 (13)0.0404 (4)
O30.3082 (2)0.66560 (16)0.44674 (14)0.0506 (5)
H3A0.38300.70420.47880.076*
O4−0.3079 (2)0.48508 (18)0.62396 (15)0.0529 (5)
C10.2137 (3)0.8092 (2)−0.2603 (2)0.0375 (5)
H1C0.20090.7931−0.34420.045*
H1D0.11840.8536−0.24240.045*
C20.3714 (3)0.8770 (2)−0.2341 (2)0.0430 (6)
H2A0.37990.9003−0.15210.052*
H2B0.36530.9426−0.28320.052*
C30.5255 (3)0.8109 (2)−0.2575 (2)0.0410 (6)
H3B0.62630.8537−0.23270.049*
C40.5291 (3)0.7026 (2)−0.1897 (2)0.0399 (6)
H4A0.62330.6591−0.21130.048*
H4B0.54730.7185−0.10580.048*
C50.3701 (3)0.6345 (2)−0.21181 (18)0.0347 (5)
H5A0.36170.6135−0.29540.042*
C60.3824 (4)0.5274 (2)−0.1411 (2)0.0465 (6)
H6A0.48960.4928−0.15040.056*
H6B0.29510.4773−0.17270.056*
C70.3649 (3)0.5455 (2)−0.0095 (2)0.0449 (6)
H7A0.36300.47450.02990.054*
H7B0.46140.58620.02510.054*
C80.2052 (3)0.6091 (2)0.01045 (19)0.0343 (5)
H8A0.11040.5640−0.02180.041*
C90.1961 (3)0.71946 (19)−0.05767 (19)0.0305 (5)
H9A0.29510.7624−0.02870.037*
C100.2087 (3)0.6997 (2)−0.19199 (18)0.0328 (5)
C110.0424 (3)0.7867 (2)−0.0302 (2)0.0420 (6)
H11A0.04660.8585−0.06750.050*
H11B−0.05810.7494−0.06340.050*
C120.0323 (3)0.8024 (2)0.1027 (2)0.0405 (6)
H12A−0.06800.84410.11510.049*
H12B0.12810.84520.13450.049*
C130.0287 (3)0.69225 (19)0.17083 (18)0.0324 (5)
C140.1819 (3)0.62930 (19)0.13928 (18)0.0320 (5)
C150.3140 (3)0.6388 (2)0.2355 (2)0.0392 (5)
H15A0.43140.64190.21770.047*
C160.2557 (3)0.7099 (2)0.33232 (19)0.0387 (6)
H16A0.30310.78400.32600.046*
C170.0623 (3)0.71678 (19)0.30680 (18)0.0336 (5)
H17A0.03130.79410.31810.040*
C180.0561 (3)0.6373 (3)−0.2475 (2)0.0516 (7)
H18A0.06750.6258−0.33000.077*
H18B−0.04330.6797−0.23850.077*
H18C0.04790.5673−0.20900.077*
C19−0.1342 (3)0.6303 (3)0.1395 (2)0.0452 (6)
H19A−0.14840.61790.05580.068*
H19B−0.22640.67320.16300.068*
H19C−0.13070.56070.18000.068*
C20−0.0349 (3)0.6490 (2)0.38948 (18)0.0329 (5)
C21−0.1599 (3)0.6964 (2)0.44449 (19)0.0358 (5)
H21A−0.18540.77030.43010.043*
C22−0.0037 (3)0.5362 (2)0.41596 (18)0.0349 (5)
H22A0.08050.49980.38000.042*
C23−0.0930 (3)0.4799 (2)0.49229 (19)0.0375 (5)
H23A−0.06890.40580.50680.045*
C24−0.2220 (3)0.5307 (2)0.55044 (19)0.0379 (6)
O1W0.3771 (3)0.4443 (2)0.5263 (2)0.0555 (5)
H1WA0.480 (5)0.462 (3)0.567 (3)0.092 (13)*
H1WB0.355 (5)0.503 (4)0.496 (3)0.084 (14)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0374 (10)0.0467 (13)0.0365 (10)0.0049 (9)0.0131 (8)0.0015 (10)
O10.0544 (10)0.0426 (11)0.0413 (9)−0.0053 (8)0.0232 (8)0.0012 (8)
O20.0541 (9)0.0351 (9)0.0335 (8)0.0123 (8)0.0119 (7)0.0039 (8)
O30.0563 (10)0.0580 (12)0.0357 (9)−0.0091 (9)−0.0054 (7)−0.0029 (9)
O40.0498 (10)0.0619 (12)0.0490 (10)−0.0076 (9)0.0154 (8)0.0124 (10)
C10.0428 (12)0.0421 (14)0.0288 (12)0.0056 (11)0.0091 (9)0.0046 (11)
C20.0593 (15)0.0318 (13)0.0403 (13)−0.0022 (12)0.0179 (11)−0.0008 (11)
C30.0437 (13)0.0431 (14)0.0380 (13)−0.0094 (11)0.0139 (10)−0.0045 (12)
C40.0373 (12)0.0458 (15)0.0379 (12)0.0043 (11)0.0105 (10)0.0002 (12)
C50.0467 (12)0.0323 (13)0.0269 (10)−0.0007 (11)0.0132 (9)−0.0032 (10)
C60.0635 (15)0.0373 (15)0.0422 (13)0.0084 (12)0.0240 (11)0.0007 (12)
C70.0616 (15)0.0407 (14)0.0353 (12)0.0193 (13)0.0209 (11)0.0068 (12)
C80.0421 (12)0.0317 (13)0.0304 (11)0.0025 (10)0.0100 (9)0.0012 (10)
C90.0351 (11)0.0301 (12)0.0274 (11)0.0008 (9)0.0084 (8)0.0013 (10)
C100.0342 (11)0.0378 (13)0.0273 (11)−0.0027 (10)0.0067 (8)0.0021 (11)
C110.0512 (14)0.0439 (16)0.0330 (13)0.0135 (12)0.0156 (10)0.0118 (11)
C120.0526 (14)0.0336 (13)0.0377 (13)0.0144 (12)0.0181 (11)0.0054 (11)
C130.0390 (12)0.0310 (12)0.0287 (11)0.0024 (10)0.0105 (9)0.0000 (10)
C140.0406 (11)0.0262 (12)0.0305 (11)0.0025 (10)0.0116 (9)0.0036 (10)
C150.0346 (11)0.0459 (15)0.0379 (12)0.0011 (11)0.0080 (9)0.0021 (12)
C160.0462 (13)0.0370 (14)0.0335 (12)−0.0076 (11)0.0065 (10)−0.0030 (11)
C170.0444 (12)0.0273 (12)0.0306 (12)0.0012 (10)0.0117 (9)−0.0019 (10)
C180.0508 (14)0.0668 (19)0.0370 (13)−0.0149 (14)0.0033 (10)−0.0092 (14)
C190.0417 (12)0.0595 (17)0.0353 (12)−0.0028 (13)0.0082 (10)−0.0001 (13)
C200.0382 (11)0.0357 (13)0.0258 (10)0.0009 (10)0.0076 (9)−0.0025 (10)
C210.0391 (12)0.0361 (13)0.0332 (11)0.0050 (11)0.0088 (9)0.0038 (11)
C220.0401 (12)0.0357 (13)0.0295 (11)0.0019 (11)0.0063 (9)−0.0037 (11)
C230.0468 (12)0.0336 (13)0.0326 (11)−0.0016 (11)0.0058 (10)0.0011 (11)
C240.0361 (12)0.0457 (15)0.0316 (11)−0.0050 (11)0.0010 (9)0.0034 (12)
O1W0.0558 (13)0.0493 (13)0.0618 (13)0.0030 (10)0.0073 (10)−0.0124 (12)

Geometric parameters (Å, º)

O1—C31.454 (3)C20—C221.417 (3)
O2—C141.456 (3)C20—C211.354 (3)
O2—C151.439 (3)C22—C231.356 (3)
O3—C161.435 (3)C23—C241.416 (3)
O4—C241.256 (3)C1—H1C0.9700
O1—H1B0.8200C1—H1D0.9700
O3—H3A0.8200C2—H2B0.9700
O1W—H1WB0.80 (5)C2—H2A0.9700
O1W—H1WA0.93 (4)C3—H3B0.9800
N1—C241.359 (3)C4—H4A0.9700
N1—C211.371 (3)C4—H4B0.9700
N1—H1A0.8600C5—H5A0.9800
C1—C21.514 (3)C6—H6B0.9700
C1—C101.539 (3)C6—H6A0.9700
C2—C31.515 (3)C7—H7B0.9700
C3—C41.521 (3)C7—H7A0.9700
C4—C51.520 (3)C8—H8A0.9800
C5—C101.548 (3)C9—H9A0.9800
C5—C61.525 (3)C11—H11A0.9700
C6—C71.530 (3)C11—H11B0.9700
C7—C81.527 (3)C12—H12A0.9700
C8—C141.512 (3)C12—H12B0.9700
C8—C91.543 (3)C15—H15A0.9800
C9—C101.557 (3)C16—H16A0.9800
C9—C111.531 (3)C17—H17A0.9800
C10—C181.525 (4)C18—H18B0.9600
C11—C121.531 (3)C18—H18A0.9600
C12—C131.544 (3)C18—H18C0.9600
C13—C191.520 (4)C19—H19B0.9600
C13—C141.515 (3)C19—H19C0.9600
C13—C171.573 (3)C19—H19A0.9600
C14—C151.457 (3)C21—H21A0.9300
C15—C161.504 (3)C22—H22A0.9300
C16—C171.553 (3)C23—H23A0.9300
C17—C201.514 (3)
C14—O2—C1560.45 (15)C3—C2—H2A109.00
C3—O1—H1B109.00C1—C2—H2A109.00
C16—O3—H3A109.00H2A—C2—H2B108.00
H1WA—O1W—H1WB99 (4)C3—C2—H2B109.00
C21—N1—C24124.38 (19)O1—C3—H3B110.00
C21—N1—H1A118.00C4—C3—H3B109.00
C24—N1—H1A118.00C2—C3—H3B109.00
C2—C1—C10115.27 (19)C3—C4—H4B109.00
C1—C2—C3110.9 (2)C5—C4—H4A109.00
O1—C3—C4108.16 (19)C5—C4—H4B109.00
C2—C3—C4110.28 (19)H4A—C4—H4B108.00
O1—C3—C2109.92 (18)C3—C4—H4A109.00
C3—C4—C5114.00 (19)C6—C5—H5A107.00
C4—C5—C10113.4 (2)C10—C5—H5A107.00
C6—C5—C10111.9 (2)C4—C5—H5A107.00
C4—C5—C6111.2 (2)C5—C6—H6B109.00
C5—C6—C7112.69 (19)C7—C6—H6A109.00
C6—C7—C8111.6 (2)C7—C6—H6B109.00
C9—C8—C14109.93 (19)H6A—C6—H6B108.00
C7—C8—C14113.71 (19)C5—C6—H6A109.00
C7—C8—C9111.45 (19)C6—C7—H7A109.00
C8—C9—C11111.21 (19)C6—C7—H7B109.00
C8—C9—C10110.74 (18)C8—C7—H7B109.00
C10—C9—C11113.87 (19)H7A—C7—H7B108.00
C5—C10—C18109.6 (2)C8—C7—H7A109.00
C1—C10—C18105.9 (2)C7—C8—H8A107.00
C1—C10—C5107.88 (19)C9—C8—H8A107.00
C9—C10—C18111.25 (19)C14—C8—H8A107.00
C1—C10—C9111.63 (19)C8—C9—H9A107.00
C5—C10—C9110.39 (18)C10—C9—H9A107.00
C9—C11—C12112.38 (19)C11—C9—H9A107.00
C11—C12—C13113.08 (19)C9—C11—H11B109.00
C14—C13—C17104.82 (18)C12—C11—H11A109.00
C12—C13—C14105.37 (18)C9—C11—H11A109.00
C14—C13—C19113.1 (2)H11A—C11—H11B108.00
C17—C13—C19113.08 (18)C12—C11—H11B109.00
C12—C13—C17108.66 (18)C11—C12—H12A109.00
C12—C13—C19111.3 (2)C13—C12—H12A109.00
O2—C14—C8115.95 (19)C13—C12—H12B109.00
O2—C14—C1559.19 (14)H12A—C12—H12B108.00
C8—C14—C13118.86 (19)C11—C12—H12B109.00
O2—C14—C13112.31 (17)O2—C15—H15A120.00
C13—C14—C15109.41 (18)C14—C15—H15A120.00
C8—C14—C15126.6 (2)C16—C15—H15A120.00
O2—C15—C16113.50 (19)O3—C16—H16A109.00
O2—C15—C1460.36 (14)C15—C16—H16A109.00
C14—C15—C16110.0 (2)C17—C16—H16A109.00
C15—C16—C17105.27 (18)C16—C17—H17A107.00
O3—C16—C17113.38 (18)C20—C17—H17A107.00
O3—C16—C15111.32 (19)C13—C17—H17A107.00
C16—C17—C20114.47 (18)C10—C18—H18B109.00
C13—C17—C20117.02 (19)C10—C18—H18C110.00
C13—C17—C16104.74 (18)C10—C18—H18A109.00
C17—C20—C21119.9 (2)H18A—C18—H18C109.00
C21—C20—C22115.8 (2)H18B—C18—H18C109.00
C17—C20—C22124.4 (2)H18A—C18—H18B109.00
N1—C21—C20121.7 (2)C13—C19—H19A109.00
C20—C22—C23121.9 (2)C13—C19—H19B109.00
C22—C23—C24121.9 (2)H19A—C19—H19B109.00
O4—C24—C23125.8 (2)H19A—C19—H19C109.00
O4—C24—N1119.9 (2)C13—C19—H19C109.00
N1—C24—C23114.4 (2)H19B—C19—H19C109.00
C2—C1—H1C108.00C20—C21—H21A119.00
C10—C1—H1C108.00N1—C21—H21A119.00
C10—C1—H1D108.00C20—C22—H22A119.00
C2—C1—H1D108.00C23—C22—H22A119.00
H1C—C1—H1D108.00C22—C23—H23A119.00
C1—C2—H2B109.00C24—C23—H23A119.00
C15—O2—C14—C8118.8 (2)C10—C9—C11—C12178.82 (19)
C15—O2—C14—C13−100.0 (2)C9—C11—C12—C13−57.6 (3)
C14—O2—C15—C16100.5 (2)C11—C12—C13—C1454.6 (2)
C24—N1—C21—C201.4 (3)C11—C12—C13—C17166.44 (19)
C21—N1—C24—O4177.9 (2)C11—C12—C13—C19−68.4 (3)
C21—N1—C24—C23−2.1 (3)C12—C13—C14—O2164.85 (17)
C10—C1—C2—C356.9 (3)C12—C13—C14—C8−55.1 (3)
C2—C1—C10—C5−53.0 (2)C12—C13—C14—C15101.1 (2)
C2—C1—C10—C968.5 (3)C17—C13—C14—O250.3 (2)
C2—C1—C10—C18−170.3 (2)C17—C13—C14—C8−169.7 (2)
C1—C2—C3—O165.1 (2)C17—C13—C14—C15−13.5 (2)
C1—C2—C3—C4−54.1 (2)C19—C13—C14—O2−73.4 (2)
O1—C3—C4—C5−66.7 (2)C19—C13—C14—C866.7 (3)
C2—C3—C4—C553.6 (3)C19—C13—C14—C15−137.1 (2)
C3—C4—C5—C6−179.94 (18)C12—C13—C17—C16−89.8 (2)
C3—C4—C5—C10−52.8 (2)C12—C13—C17—C20142.3 (2)
C4—C5—C6—C774.5 (3)C14—C13—C17—C1622.5 (2)
C10—C5—C6—C7−53.5 (3)C14—C13—C17—C20−105.5 (2)
C4—C5—C10—C149.7 (2)C19—C13—C17—C16146.2 (2)
C4—C5—C10—C9−72.6 (2)C19—C13—C17—C2018.2 (3)
C4—C5—C10—C18164.56 (19)O2—C14—C15—C16−106.3 (2)
C6—C5—C10—C1176.39 (18)C8—C14—C15—O2−101.1 (2)
C6—C5—C10—C954.2 (3)C8—C14—C15—C16152.6 (2)
C6—C5—C10—C18−68.7 (2)C13—C14—C15—O2104.98 (19)
C5—C6—C7—C853.6 (3)C13—C14—C15—C16−1.3 (3)
C6—C7—C8—C9−55.0 (3)O2—C15—C16—O373.6 (2)
C6—C7—C8—C14−180.0 (2)O2—C15—C16—C17−49.7 (2)
C7—C8—C9—C1056.5 (2)C14—C15—C16—O3139.0 (2)
C7—C8—C9—C11−175.82 (18)C14—C15—C16—C1715.8 (2)
C14—C8—C9—C10−176.48 (19)O3—C16—C17—C13−145.25 (19)
C14—C8—C9—C11−48.8 (3)O3—C16—C17—C20−15.8 (3)
C7—C8—C14—O2−41.8 (3)C15—C16—C17—C13−23.3 (2)
C7—C8—C14—C13179.6 (2)C15—C16—C17—C20106.2 (2)
C7—C8—C14—C1527.8 (3)C13—C17—C20—C21−107.9 (2)
C9—C8—C14—O2−167.51 (19)C13—C17—C20—C2272.7 (3)
C9—C8—C14—C1353.9 (3)C16—C17—C20—C21129.0 (2)
C9—C8—C14—C15−97.9 (3)C16—C17—C20—C22−50.4 (3)
C8—C9—C10—C1−175.57 (19)C17—C20—C21—N1−179.4 (2)
C8—C9—C10—C5−55.6 (3)C22—C20—C21—N10.0 (3)
C8—C9—C10—C1866.3 (3)C17—C20—C22—C23178.9 (2)
C11—C9—C10—C158.2 (3)C21—C20—C22—C23−0.5 (3)
C11—C9—C10—C5178.21 (19)C20—C22—C23—C24−0.3 (4)
C11—C9—C10—C18−59.9 (3)C22—C23—C24—O4−178.5 (2)
C8—C9—C11—C1252.9 (3)C22—C23—C24—N11.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O4i0.93 (4)1.79 (4)2.710 (3)170 (4)
O1W—H1WB···O30.80 (5)2.07 (5)2.867 (3)170 (4)
N1—H1A···O1ii0.862.002.839 (3)165
O1—H1B···O1Wiii0.821.902.690 (3)161
O3—H3A···O1iv0.822.092.868 (2)157

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

Footnotes

Supporting information for this paper is available from the IUCr electronic archives (Reference: ZS2298).

Acknowledgments

This work was supported by the 111 Project (No. B13038) from the Ministry of Education of the People’s Republic of China.

References

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  • 3. Rohrer, D. C., Fullerton, D. S., Kitatsuji, E., Nambara, T. & Yoshii, E. (1982). Acta Cryst. B38, 1865–1868.
  • 4. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
  • 5. Tian, H. Y., Luo, S. L., Liu, J. S., Wang, L., Wang, Y., Zhang, D. M., Zhang, X. Q., Jiang, R. W. & Ye, W. C. (2013). J. Nat. Prod.76, 1842–1847.
  • 6. Yu, C. H., Kan, S. F., Pu, H. F., Chien, E. J. & Wang, P. S. (2008). Cancer Sci.99, 2467–2476.
  • 7. Zhan, J., Liu, W., Guo, H., Zhang, Y. & Guo, D. (2003). Enzyme Microb. Tech.33, 29–32.
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