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

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ISSN: 2056-9890

Bonvalotidine A acetone solvate from Delphinium bonvalotii Franch

aDepartment of Chemistry and Life Sciences, Leshan Teachers College, Leshan 614004, People's Republic of China
*Correspondence e-mail: fzchen7200@163.com

(Received 28 October 2010; accepted 16 November 2010; online 27 November 2010)

The title compound (systematic name: 5,6β-dihy­droxy-1α,14α,16β-trimeth­oxy-4-methyl-7β,8-methyl­enedi­oxy-20-ethyl­aconitan-6-yl acetate acetone monosolvate), C27H41NO8·C3H6O, was isolated from Delphinium bonvalotii Franch, and is a typical C19-diterpenoid alkaloid. The mol­ecule has a lycoctonine carbon skeleton with four six-membered rings and three five-membered rings. Three six-membered rings adopt the chair conformations while the fourth adopts a boat conformation, while the five-membered rings have the envelope conformations. The solvent mol­ecule links with the organic mol­ecule via a classical O—H⋯O hydrogen bond. Weak C—H⋯O hydrogen bonding is present in the structure. An intra­molecular O—H⋯O hydrogen bond also occurs.

Related literature

For the chemical structure of the title compound established from NMR and MS data, see: He et al. (2006[He, Y., Chen, D.-L. & Wang, F.-P. (2006). Nat. Prod. Commun. 5, 357-362.]). For the crystal structures of related C19-diterpenoid alkaloids, see: Wang et al. (2009[Wang, F.-P., Chen, Q.-H. & Liu, X.-Y. (2009). The Alkaloids: Chemistry and Bioloy, Vol. 67, edited by G. A. Cordell, pp. 1-78. New York: Elsevier.]).

[Scheme 1]

Experimental

Crystal data
  • C27H41NO8·C3H6O

  • Mr = 565.69

  • Orthorhombic, P 21 21 21

  • a = 8.4260 (8) Å

  • b = 9.5546 (7) Å

  • c = 35.237 (3) Å

  • V = 2836.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 120 K

  • 0.42 × 0.36 × 0.21 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 9839 measured reflections

  • 2930 independent reflections

  • 2690 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.104

  • S = 1.08

  • 2930 reflections

  • 373 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.69 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O3 0.99 (5) 2.00 (5) 2.605 (3) 118 (4)
O2—H2⋯O9 0.99 (5) 2.13 (5) 2.936 (4) 138 (4)
C24—H24A⋯O9 0.98 2.53 3.427 (5) 153
C25—H25A⋯O2i 0.99 2.36 3.344 (4) 170
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al. 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, bonvalotidine A, was previously isolated from Delphinium bonvalotii Franch (He et al. 2006), and its structure was established from the NMR and MS data. In our recent investigation, it was isolation from the root of Delphinium bonvalotii Franch collected in the E'mei Mountain, Sichuan Province of P. R. China in September, 2009. A nd its crystal structure was determined. The naming conforming referred to the literature (Wang et al. 2009). The molecular structure of the title compound is shown in Fig. 1. Six-membered rings A (C1/C2/C3/C4/C5/C11) and B (C7/C8/C9/C10/C11/C17) adopt chair conformations; six-membered ring D (C8/C9/C14/C13/C16/C15) adopt a boat conformation; six-membered N-containing heterocyclic ring E (C4/C5/C11/C17/N1/C19) displays the same chair conformation; five-membered rings C (C9/C10/C12/C13/C14) and F (C5/C6/C7/C17/C11) adopt an envelope conformation. While the five-membered O-containing heterocyclic G (O5/C7/C8/O6/C25) displays an envelope conformation.

The crystal structure contains intermolecular O—H···O hydrogen bond between the hydroxyl group and carbonyl O atom. The lattice acetone molecule links with the organic molecule via O—H···O hydrogen is present in the crystal structure (Table 1).

Related literature top

For the chemical structure of the title compound established from NMR and MS data, see: He et al. (2006). For the crystal structures of related C19-diterpenoid alkaloids, see: Wang et al. (2009).

Experimental top

The title compound was isolated from the root of Delphinium bonvalotii Franch. Single crystals suitable for X-ray structure analysis were obtained by slow evaporation from an acetone solution at room temperature.

Refinement top

Hydroxy H atom was located in a difference Fourier map and refined isotropically. Other H atoms were located geometrically with C—H = 0.98–1.00 Å, and refined using a riding model with Uiso(H) = 1.2 Ueq(C). As no significant anomalous scatterings, Friedel pairs were merged.

Structure description top

The title compound, bonvalotidine A, was previously isolated from Delphinium bonvalotii Franch (He et al. 2006), and its structure was established from the NMR and MS data. In our recent investigation, it was isolation from the root of Delphinium bonvalotii Franch collected in the E'mei Mountain, Sichuan Province of P. R. China in September, 2009. A nd its crystal structure was determined. The naming conforming referred to the literature (Wang et al. 2009). The molecular structure of the title compound is shown in Fig. 1. Six-membered rings A (C1/C2/C3/C4/C5/C11) and B (C7/C8/C9/C10/C11/C17) adopt chair conformations; six-membered ring D (C8/C9/C14/C13/C16/C15) adopt a boat conformation; six-membered N-containing heterocyclic ring E (C4/C5/C11/C17/N1/C19) displays the same chair conformation; five-membered rings C (C9/C10/C12/C13/C14) and F (C5/C6/C7/C17/C11) adopt an envelope conformation. While the five-membered O-containing heterocyclic G (O5/C7/C8/O6/C25) displays an envelope conformation.

The crystal structure contains intermolecular O—H···O hydrogen bond between the hydroxyl group and carbonyl O atom. The lattice acetone molecule links with the organic molecule via O—H···O hydrogen is present in the crystal structure (Table 1).

For the chemical structure of the title compound established from NMR and MS data, see: He et al. (2006). For the crystal structures of related C19-diterpenoid alkaloids, see: Wang et al. (2009).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al. 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of thetitle compound with 30% probabiliy displacement ellipsoids for no-H atoms. Hatoms have been omitted clarity. Dashed line indicates hydrogen bonding.
5,6β-dihydroxy-1α,14α,16β-trimethoxy-4-methyl-7β,8-methylenedioxy- 20-ethylaconitan-6-yl acetate acetone monosolvate top
Crystal data top
C27H41NO8·C3H6OF(000) = 1224
Mr = 565.69Dx = 1.324 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6568 reflections
a = 8.4260 (8) Åθ = 3.1–25.0°
b = 9.5546 (7) ŵ = 0.10 mm1
c = 35.237 (3) ÅT = 120 K
V = 2836.8 (4) Å3Block, colorless
Z = 40.42 × 0.36 × 0.21 mm
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
2690 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.2°, θmin = 3.2°
ω scanh = 109
9839 measured reflectionsk = 1111
2930 independent reflectionsl = 2242
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0438P)2 + 2.2374P]
where P = (Fo2 + 2Fc2)/3
2930 reflections(Δ/σ)max = 0.002
373 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C27H41NO8·C3H6OV = 2836.8 (4) Å3
Mr = 565.69Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.4260 (8) ŵ = 0.10 mm1
b = 9.5546 (7) ÅT = 120 K
c = 35.237 (3) Å0.42 × 0.36 × 0.21 mm
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
2690 reflections with I > 2σ(I)
9839 measured reflectionsRint = 0.022
2930 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.69 e Å3
2930 reflectionsΔρmin = 0.27 e Å3
373 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
xyzUiso*/Ueq
O10.6059 (3)0.7225 (2)0.47254 (6)0.0246 (5)
O20.7919 (3)0.6104 (3)0.35691 (7)0.0269 (6)
O30.5491 (3)0.5711 (2)0.31240 (6)0.0184 (5)
O40.4301 (4)0.3889 (3)0.28401 (7)0.0398 (7)
O50.2412 (3)0.4687 (2)0.36445 (6)0.0189 (5)
O60.2372 (3)0.6543 (2)0.32229 (6)0.0186 (5)
O70.2550 (3)0.9818 (2)0.32957 (6)0.0223 (5)
O80.0416 (3)0.9541 (3)0.40687 (7)0.0329 (6)
O90.8945 (3)0.6682 (3)0.27882 (8)0.0436 (7)
N10.4624 (3)0.4363 (3)0.43288 (7)0.0173 (6)
C10.6960 (4)0.6670 (3)0.44119 (9)0.0231 (7)
H10.77960.73710.43450.028*
C20.7798 (4)0.5360 (4)0.45604 (10)0.0271 (8)
H2A0.86830.56450.47280.033*
H2B0.70410.48060.47140.033*
C30.8446 (4)0.4447 (4)0.42437 (10)0.0271 (8)
H3A0.88700.35680.43530.033*
H3B0.93320.49400.41160.033*
C40.7166 (4)0.4097 (3)0.39515 (9)0.0214 (7)
C50.6632 (4)0.5480 (3)0.37573 (9)0.0182 (7)
C60.5217 (4)0.5115 (3)0.34940 (8)0.0161 (6)
H60.51730.40740.34660.019*
C70.3717 (4)0.5591 (3)0.37131 (9)0.0151 (6)
C80.3050 (4)0.7005 (3)0.35823 (9)0.0180 (7)
C90.4386 (4)0.8063 (3)0.35323 (8)0.0161 (6)
H90.49630.79010.32880.019*
C100.5551 (4)0.7971 (3)0.38791 (9)0.0191 (7)
H100.65990.83310.37890.023*
C110.5873 (4)0.6482 (3)0.40582 (9)0.0169 (7)
C120.4868 (5)0.9106 (3)0.41606 (9)0.0287 (8)
H12A0.46220.86750.44090.034*
H12B0.56540.98620.42000.034*
C130.3358 (4)0.9694 (3)0.39794 (9)0.0255 (8)
H130.31951.06930.40540.031*
C140.3782 (4)0.9577 (3)0.35576 (9)0.0204 (7)
H140.46801.02290.35010.024*
C150.1656 (4)0.7551 (3)0.38249 (10)0.0232 (7)
H15B0.07820.77940.36490.028*
H15A0.12780.67630.39830.028*
C160.1906 (4)0.8800 (3)0.40873 (9)0.0257 (8)
H160.20560.84450.43520.031*
C170.4316 (4)0.5675 (3)0.41273 (8)0.0158 (6)
H170.35750.62670.42800.019*
C180.7886 (4)0.3079 (4)0.36619 (10)0.0284 (8)
H18B0.89070.34440.35730.043*
H18C0.71620.29780.34460.043*
H18A0.80470.21640.37820.043*
C190.5701 (4)0.3402 (3)0.41337 (9)0.0202 (7)
H19B0.50990.29080.39330.024*
H19A0.60690.26900.43180.024*
C200.3177 (4)0.3659 (3)0.44604 (9)0.0234 (7)
H20B0.27030.31310.42470.028*
H20A0.23970.43710.45430.028*
C210.3508 (5)0.2660 (4)0.47871 (10)0.0301 (8)
H21C0.41150.18560.46940.045*
H21B0.25020.23360.48950.045*
H21A0.41220.31460.49830.045*
C220.6932 (5)0.8197 (4)0.49485 (10)0.0325 (9)
H22B0.79690.77960.50120.049*
H22A0.63460.83990.51820.049*
H22C0.70840.90640.48050.049*
C230.4946 (4)0.5004 (3)0.28192 (9)0.0241 (7)
C240.5246 (5)0.5798 (4)0.24627 (9)0.0305 (9)
H24C0.51600.51650.22450.046*
H24A0.63130.62040.24710.046*
H24B0.44600.65490.24380.046*
C250.1621 (4)0.5249 (3)0.33175 (9)0.0215 (7)
H25B0.17000.45870.31020.026*
H25A0.04840.54060.33740.026*
C260.2066 (5)1.1253 (3)0.32951 (10)0.0296 (8)
H26A0.14791.14570.35290.044*
H26C0.13831.14290.30750.044*
H26B0.30061.18560.32810.044*
C270.0114 (5)1.0354 (4)0.43882 (11)0.0390 (9)
H27A0.01910.97700.46160.059*
H27C0.09551.07520.43700.059*
H27B0.08951.11120.44030.059*
C280.9445 (5)0.7871 (4)0.27569 (11)0.0359 (9)
C291.0840 (5)0.8220 (5)0.25177 (11)0.0398 (10)
H29C1.11230.74090.23620.060*
H29A1.17390.84690.26810.060*
H29B1.05800.90130.23530.060*
C300.8676 (6)0.9039 (5)0.29680 (14)0.0504 (12)
H30B0.76760.87110.30790.076*
H30C0.84600.98140.27930.076*
H30A0.93840.93610.31710.076*
H20.769 (5)0.618 (5)0.3296 (13)0.059 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0318 (13)0.0243 (12)0.0178 (11)0.0064 (11)0.0067 (10)0.0012 (10)
O20.0167 (12)0.0326 (13)0.0315 (14)0.0044 (10)0.0015 (11)0.0099 (11)
O30.0217 (11)0.0168 (11)0.0165 (10)0.0010 (9)0.0041 (9)0.0009 (9)
O40.0657 (19)0.0266 (13)0.0271 (13)0.0164 (14)0.0058 (14)0.0070 (11)
O50.0163 (10)0.0202 (11)0.0203 (11)0.0043 (10)0.0014 (9)0.0020 (9)
O60.0179 (11)0.0204 (11)0.0174 (11)0.0032 (10)0.0009 (9)0.0010 (9)
O70.0299 (12)0.0156 (11)0.0214 (11)0.0038 (10)0.0032 (11)0.0038 (9)
O80.0400 (14)0.0306 (13)0.0281 (13)0.0117 (13)0.0030 (12)0.0015 (12)
O90.0386 (16)0.0432 (16)0.0491 (17)0.0146 (14)0.0111 (14)0.0109 (14)
N10.0213 (13)0.0133 (12)0.0175 (12)0.0007 (11)0.0019 (11)0.0027 (11)
C10.0236 (17)0.0188 (16)0.0270 (17)0.0058 (14)0.0051 (15)0.0059 (14)
C20.0289 (18)0.0255 (17)0.0268 (17)0.0038 (16)0.0118 (16)0.0082 (15)
C30.0211 (16)0.0280 (17)0.0323 (19)0.0018 (16)0.0058 (16)0.0121 (16)
C40.0194 (16)0.0182 (15)0.0265 (17)0.0022 (14)0.0038 (14)0.0054 (14)
C50.0142 (15)0.0175 (15)0.0230 (16)0.0006 (13)0.0002 (14)0.0056 (14)
C60.0198 (15)0.0131 (14)0.0153 (15)0.0009 (13)0.0045 (13)0.0031 (12)
C70.0155 (15)0.0146 (14)0.0152 (15)0.0039 (13)0.0002 (13)0.0016 (13)
C80.0195 (16)0.0187 (15)0.0157 (15)0.0025 (13)0.0004 (13)0.0001 (13)
C90.0215 (15)0.0149 (14)0.0118 (14)0.0003 (13)0.0011 (13)0.0013 (12)
C100.0260 (17)0.0144 (15)0.0171 (15)0.0048 (14)0.0060 (14)0.0024 (13)
C110.0192 (16)0.0148 (15)0.0166 (15)0.0022 (13)0.0038 (13)0.0036 (12)
C120.048 (2)0.0183 (16)0.0202 (16)0.0011 (17)0.0103 (17)0.0036 (14)
C130.043 (2)0.0161 (15)0.0170 (16)0.0085 (16)0.0071 (15)0.0017 (13)
C140.0310 (18)0.0135 (14)0.0167 (15)0.0001 (14)0.0027 (15)0.0020 (13)
C150.0216 (16)0.0235 (16)0.0246 (17)0.0042 (15)0.0049 (14)0.0022 (14)
C160.037 (2)0.0241 (17)0.0161 (16)0.0129 (16)0.0013 (15)0.0044 (14)
C170.0185 (15)0.0127 (14)0.0162 (15)0.0012 (13)0.0005 (13)0.0014 (13)
C180.0256 (18)0.0260 (17)0.0334 (19)0.0099 (15)0.0078 (16)0.0069 (15)
C190.0223 (16)0.0166 (15)0.0218 (16)0.0007 (14)0.0025 (14)0.0053 (13)
C200.0256 (17)0.0221 (16)0.0227 (17)0.0020 (15)0.0062 (15)0.0038 (14)
C210.037 (2)0.0283 (18)0.0254 (19)0.0100 (17)0.0003 (16)0.0055 (15)
C220.041 (2)0.0332 (19)0.0238 (18)0.0082 (18)0.0118 (17)0.0003 (16)
C230.0291 (17)0.0205 (16)0.0226 (17)0.0002 (15)0.0054 (15)0.0046 (14)
C240.036 (2)0.036 (2)0.0194 (16)0.0043 (18)0.0030 (16)0.0003 (15)
C250.0187 (15)0.0217 (16)0.0241 (17)0.0033 (14)0.0024 (14)0.0023 (14)
C260.043 (2)0.0215 (17)0.0241 (18)0.0090 (16)0.0003 (17)0.0026 (14)
C270.036 (2)0.044 (2)0.037 (2)0.007 (2)0.0103 (18)0.0029 (18)
C280.0307 (19)0.041 (2)0.036 (2)0.0108 (18)0.0177 (18)0.0152 (19)
C290.043 (2)0.045 (2)0.032 (2)0.008 (2)0.0068 (19)0.0083 (19)
C300.041 (2)0.048 (3)0.062 (3)0.003 (2)0.001 (2)0.017 (2)
Geometric parameters (Å, º) top
O1—C221.421 (4)C12—C131.531 (5)
O1—C11.442 (4)C12—H12A0.9900
O2—C51.404 (4)C12—H12B0.9900
O2—H20.99 (5)C13—C141.533 (4)
O3—C231.349 (4)C13—C161.540 (5)
O3—C61.441 (3)C13—H131.0000
O4—C231.198 (4)C14—H141.0000
O5—C71.419 (4)C15—C161.524 (5)
O5—C251.436 (4)C15—H15B0.9900
O6—C251.429 (4)C15—H15A0.9900
O6—C81.457 (4)C16—H161.0000
O7—C141.408 (4)C17—H171.0000
O7—C261.431 (4)C18—H18B0.9800
O8—C271.391 (4)C18—H18C0.9800
O8—C161.443 (4)C18—H18A0.9800
O9—C281.217 (5)C19—H19B0.9900
N1—C191.462 (4)C19—H19A0.9900
N1—C171.464 (4)C20—C211.521 (4)
N1—C201.468 (4)C20—H20B0.9900
C1—C21.530 (5)C20—H20A0.9900
C1—C111.557 (4)C21—H21C0.9800
C1—H11.0000C21—H21B0.9800
C2—C31.518 (5)C21—H21A0.9800
C2—H2A0.9900C22—H22B0.9800
C2—H2B0.9900C22—H22A0.9800
C3—C41.528 (5)C22—H22C0.9800
C3—H3A0.9900C23—C241.489 (5)
C3—H3B0.9900C24—H24C0.9800
C4—C181.535 (5)C24—H24A0.9800
C4—C191.542 (4)C24—H24B0.9800
C4—C51.555 (4)C25—H25B0.9900
C5—C61.550 (4)C25—H25A0.9900
C5—C111.566 (4)C26—H26A0.9800
C6—C71.549 (4)C26—H26C0.9800
C6—H61.0000C26—H26B0.9800
C7—C81.534 (4)C27—H27A0.9800
C7—C171.547 (4)C27—H27C0.9800
C8—C91.523 (4)C27—H27B0.9800
C8—C151.544 (4)C28—C291.484 (6)
C9—C141.536 (4)C28—C301.490 (6)
C9—C101.570 (4)C29—H29C0.9800
C9—H91.0000C29—H29A0.9800
C10—C121.578 (4)C29—H29B0.9800
C10—C111.579 (4)C30—H30B0.9800
C10—H101.0000C30—H30C0.9800
C11—C171.541 (4)C30—H30A0.9800
C22—O1—C1113.1 (3)C13—C14—H14109.0
C5—O2—H2110 (3)C9—C14—H14109.0
C23—O3—C6117.9 (2)C16—C15—C8119.7 (3)
C7—O5—C25105.6 (2)C16—C15—H15B107.4
C25—O6—C8103.5 (2)C8—C15—H15B107.4
C14—O7—C26111.6 (3)C16—C15—H15A107.4
C27—O8—C16113.3 (3)C8—C15—H15A107.4
C19—N1—C17114.8 (2)H15B—C15—H15A106.9
C19—N1—C20112.1 (2)O8—C16—C15103.7 (3)
C17—N1—C20113.5 (2)O8—C16—C13114.1 (3)
O1—C1—C2106.4 (3)C15—C16—C13113.2 (3)
O1—C1—C11110.2 (3)O8—C16—H16108.5
C2—C1—C11116.8 (3)C15—C16—H16108.5
O1—C1—H1107.7C13—C16—H16108.5
C2—C1—H1107.7N1—C17—C11110.7 (2)
C11—C1—H1107.7N1—C17—C7118.1 (2)
C3—C2—C1112.6 (3)C11—C17—C798.9 (2)
C3—C2—H2A109.1N1—C17—H17109.5
C1—C2—H2A109.1C11—C17—H17109.5
C3—C2—H2B109.1C7—C17—H17109.5
C1—C2—H2B109.1C4—C18—H18B109.5
H2A—C2—H2B107.8C4—C18—H18C109.5
C2—C3—C4111.5 (3)H18B—C18—H18C109.5
C2—C3—H3A109.3C4—C18—H18A109.5
C4—C3—H3A109.3H18B—C18—H18A109.5
C2—C3—H3B109.3H18C—C18—H18A109.5
C4—C3—H3B109.3N1—C19—C4115.0 (3)
H3A—C3—H3B108.0N1—C19—H19B108.5
C3—C4—C18107.9 (3)C4—C19—H19B108.5
C3—C4—C19112.3 (3)N1—C19—H19A108.5
C18—C4—C19108.7 (3)C4—C19—H19A108.5
C3—C4—C5108.4 (3)H19B—C19—H19A107.5
C18—C4—C5111.1 (3)N1—C20—C21112.0 (3)
C19—C4—C5108.5 (2)N1—C20—H20B109.2
O2—C5—C6114.0 (3)C21—C20—H20B109.2
O2—C5—C4110.2 (2)N1—C20—H20A109.2
C6—C5—C4107.2 (2)C21—C20—H20A109.2
O2—C5—C11112.0 (3)H20B—C20—H20A107.9
C6—C5—C11103.2 (2)C20—C21—H21C109.5
C4—C5—C11109.9 (3)C20—C21—H21B109.5
O3—C6—C7117.8 (2)H21C—C21—H21B109.5
O3—C6—C5109.2 (2)C20—C21—H21A109.5
C7—C6—C5105.3 (2)H21C—C21—H21A109.5
O3—C6—H6108.1H21B—C21—H21A109.5
C7—C6—H6108.1O1—C22—H22B109.5
C5—C6—H6108.1O1—C22—H22A109.5
O5—C7—C8101.6 (2)H22B—C22—H22A109.5
O5—C7—C17116.4 (2)O1—C22—H22C109.5
C8—C7—C17110.9 (2)H22B—C22—H22C109.5
O5—C7—C6111.6 (2)H22A—C22—H22C109.5
C8—C7—C6114.1 (2)O4—C23—O3123.4 (3)
C17—C7—C6102.7 (2)O4—C23—C24125.6 (3)
O6—C8—C9112.9 (2)O3—C23—C24111.0 (3)
O6—C8—C798.0 (2)C23—C24—H24C109.5
C9—C8—C7110.4 (2)C23—C24—H24A109.5
O6—C8—C15106.6 (2)H24C—C24—H24A109.5
C9—C8—C15113.7 (3)C23—C24—H24B109.5
C7—C8—C15114.2 (3)H24C—C24—H24B109.5
C8—C9—C14112.0 (3)H24A—C24—H24B109.5
C8—C9—C10109.6 (2)O6—C25—O5107.8 (2)
C14—C9—C10102.4 (2)O6—C25—H25B110.2
C8—C9—H9110.9O5—C25—H25B110.2
C14—C9—H9110.9O6—C25—H25A110.2
C10—C9—H9110.9O5—C25—H25A110.2
C9—C10—C12102.9 (2)H25B—C25—H25A108.5
C9—C10—C11118.0 (2)O7—C26—H26A109.5
C12—C10—C11115.5 (2)O7—C26—H26C109.5
C9—C10—H10106.6H26A—C26—H26C109.5
C12—C10—H10106.6O7—C26—H26B109.5
C11—C10—H10106.6H26A—C26—H26B109.5
C17—C11—C1115.6 (2)H26C—C26—H26B109.5
C17—C11—C598.5 (2)O8—C27—H27A109.5
C1—C11—C5111.9 (3)O8—C27—H27C109.5
C17—C11—C10111.6 (2)H27A—C27—H27C109.5
C1—C11—C10108.5 (2)O8—C27—H27B109.5
C5—C11—C10110.5 (2)H27A—C27—H27B109.5
C13—C12—C10107.1 (3)H27C—C27—H27B109.5
C13—C12—H12A110.3O9—C28—C29122.4 (4)
C10—C12—H12A110.3O9—C28—C30120.2 (4)
C13—C12—H12B110.3C29—C28—C30117.4 (3)
C10—C12—H12B110.3C28—C29—H29C109.5
H12A—C12—H12B108.6C28—C29—H29A109.5
C12—C13—C14100.6 (3)H29C—C29—H29A109.5
C12—C13—C16110.7 (3)C28—C29—H29B109.5
C14—C13—C16112.6 (3)H29C—C29—H29B109.5
C12—C13—H13110.8H29A—C29—H29B109.5
C14—C13—H13110.8C28—C30—H30B109.5
C16—C13—H13110.8C28—C30—H30C109.5
O7—C14—C13116.8 (3)H30B—C30—H30C109.5
O7—C14—C9111.1 (2)C28—C30—H30A109.5
C13—C14—C9101.7 (2)H30B—C30—H30A109.5
O7—C14—H14109.0H30C—C30—H30A109.5
C22—O1—C1—C289.7 (3)O2—C5—C11—C172.0 (3)
C22—O1—C1—C11142.7 (3)C6—C5—C11—C1164.8 (2)
O1—C1—C2—C3165.1 (3)C4—C5—C11—C150.8 (3)
C11—C1—C2—C341.5 (4)O2—C5—C11—C1049.0 (3)
C1—C2—C3—C452.8 (4)C6—C5—C11—C1074.2 (3)
C2—C3—C4—C18175.4 (3)C4—C5—C11—C10171.8 (2)
C2—C3—C4—C1955.6 (4)C9—C10—C11—C1747.6 (4)
C2—C3—C4—C564.2 (3)C12—C10—C11—C1774.5 (3)
C3—C4—C5—O261.2 (3)C9—C10—C11—C1176.1 (3)
C18—C4—C5—O257.2 (4)C12—C10—C11—C153.9 (4)
C19—C4—C5—O2176.6 (3)C9—C10—C11—C560.9 (4)
C3—C4—C5—C6174.2 (2)C12—C10—C11—C5176.9 (3)
C18—C4—C5—C667.4 (3)C9—C10—C12—C133.4 (3)
C19—C4—C5—C652.1 (3)C11—C10—C12—C13126.5 (3)
C3—C4—C5—C1162.7 (3)C10—C12—C13—C1431.9 (3)
C18—C4—C5—C11178.8 (3)C10—C12—C13—C1687.4 (3)
C19—C4—C5—C1159.4 (3)C26—O7—C14—C1368.7 (4)
C23—O3—C6—C793.5 (3)C26—O7—C14—C9175.3 (3)
C23—O3—C6—C5146.6 (3)C12—C13—C14—O7169.9 (3)
O2—C5—C6—O38.6 (3)C16—C13—C14—O752.0 (4)
C4—C5—C6—O3130.9 (3)C12—C13—C14—C948.8 (3)
C11—C5—C6—O3113.1 (3)C16—C13—C14—C969.1 (3)
O2—C5—C6—C7136.0 (3)C8—C9—C14—O755.1 (3)
C4—C5—C6—C7101.8 (3)C10—C9—C14—O7172.4 (2)
C11—C5—C6—C714.2 (3)C8—C9—C14—C1369.9 (3)
C25—O5—C7—C832.6 (3)C10—C9—C14—C1347.3 (3)
C25—O5—C7—C17153.2 (3)O6—C8—C15—C16144.4 (3)
C25—O5—C7—C689.4 (3)C9—C8—C15—C1619.3 (4)
O3—C6—C7—O592.7 (3)C7—C8—C15—C16108.6 (3)
C5—C6—C7—O5145.3 (2)C27—O8—C16—C15155.1 (3)
O3—C6—C7—C821.7 (4)C27—O8—C16—C1381.3 (4)
C5—C6—C7—C8100.2 (3)C8—C15—C16—O8144.4 (3)
O3—C6—C7—C17141.8 (3)C8—C15—C16—C1320.2 (4)
C5—C6—C7—C1719.9 (3)C12—C13—C16—O8155.7 (3)
C25—O6—C8—C9159.4 (2)C14—C13—C16—O892.6 (3)
C25—O6—C8—C743.2 (3)C12—C13—C16—C1586.1 (3)
C25—O6—C8—C1575.1 (3)C14—C13—C16—C1525.7 (4)
O5—C7—C8—O646.9 (3)C19—N1—C17—C1159.0 (3)
C17—C7—C8—O6171.3 (2)C20—N1—C17—C11170.3 (3)
C6—C7—C8—O673.4 (3)C19—N1—C17—C753.9 (4)
O5—C7—C8—C9165.0 (2)C20—N1—C17—C776.8 (3)
C17—C7—C8—C970.6 (3)C1—C11—C17—N149.6 (3)
C6—C7—C8—C944.8 (3)C5—C11—C17—N169.7 (3)
O5—C7—C8—C1565.4 (3)C10—C11—C17—N1174.2 (2)
C17—C7—C8—C1559.0 (3)C1—C11—C17—C7174.3 (3)
C6—C7—C8—C15174.3 (3)C5—C11—C17—C755.0 (3)
O6—C8—C9—C1494.0 (3)C10—C11—C17—C761.2 (3)
C7—C8—C9—C14157.4 (3)O5—C7—C17—N149.7 (4)
C15—C8—C9—C1427.6 (4)C8—C7—C17—N1165.2 (3)
O6—C8—C9—C10153.1 (2)C6—C7—C17—N172.6 (3)
C7—C8—C9—C1044.6 (3)O5—C7—C17—C11169.0 (2)
C15—C8—C9—C1085.3 (3)C8—C7—C17—C1175.5 (3)
C8—C9—C10—C1292.5 (3)C6—C7—C17—C1146.8 (3)
C14—C9—C10—C1226.5 (3)C17—N1—C19—C442.6 (4)
C8—C9—C10—C1135.9 (4)C20—N1—C19—C4174.0 (3)
C14—C9—C10—C11154.9 (3)C3—C4—C19—N177.9 (3)
O1—C1—C11—C1750.8 (3)C18—C4—C19—N1162.8 (3)
C2—C1—C11—C1770.8 (4)C5—C4—C19—N141.9 (4)
O1—C1—C11—C5162.5 (2)C19—N1—C20—C2170.1 (3)
C2—C1—C11—C540.9 (4)C17—N1—C20—C21157.8 (3)
O1—C1—C11—C1075.3 (3)C6—O3—C23—O42.8 (5)
C2—C1—C11—C10163.1 (3)C6—O3—C23—C24176.8 (3)
O2—C5—C11—C17165.9 (2)C8—O6—C25—O525.3 (3)
C6—C5—C11—C1742.8 (3)C7—O5—C25—O65.7 (3)
C4—C5—C11—C1771.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.99 (5)2.00 (5)2.605 (3)118 (4)
O2—H2···O90.99 (5)2.13 (5)2.936 (4)138 (4)
C24—H24A···O90.982.533.427 (5)153
C25—H25A···O2i0.992.363.344 (4)170
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC27H41NO8·C3H6O
Mr565.69
Crystal system, space groupOrthorhombic, P212121
Temperature (K)120
a, b, c (Å)8.4260 (8), 9.5546 (7), 35.237 (3)
V3)2836.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.42 × 0.36 × 0.21
Data collection
DiffractometerOxford Diffraction Xcalibur Eos
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9839, 2930, 2690
Rint0.022
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.104, 1.08
No. of reflections2930
No. of parameters373
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.69, 0.27

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al. 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.99 (5)2.00 (5)2.605 (3)118 (4)
O2—H2···O90.99 (5)2.13 (5)2.936 (4)138 (4)
C24—H24A···O90.982.533.427 (5)153
C25—H25A···O2i0.992.363.344 (4)170
Symmetry code: (i) x1, y, z.
 

Acknowledgements

This project was supported by the Scientific Reseach Fund of Leshan Teachers' College, China (grant No. Z0975)

References

First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationHe, Y., Chen, D.-L. & Wang, F.-P. (2006). Nat. Prod. Commun. 5, 357–362.  Google Scholar
First citationOxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, F.-P., Chen, Q.-H. & Liu, X.-Y. (2009). The Alkaloids: Chemistry and Bioloy, Vol. 67, edited by G. A. Cordell, pp. 1–78. New York: Elsevier.  Google Scholar

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