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

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ISSN: 2056-9890

Anthriscifolcine A, a C18-diterpenoid alkaloid

aKey Laboratory of Natural Pesticides and Chemical Biology, South China Agricultural University, Guangzhou 510642, People's Republic of China, and bCollege of Agriculture, Yangtze University, Jingzhou, Hubei 434025, People's Republic of China
*Correspondence e-mail: hhxu@scau.edu.cn

(Received 30 December 2010; accepted 10 January 2011; online 15 January 2011)

The title compound, C26H39NO7, which was isolated from Delphinium anthriscifolium var. majus, has a lycoctonine carbon skeleton containing four six-membered rings (A, B, D and E) and three five-membered rings (C, F and G). Rings A, B and E adopt chair conformation, while ring D adopts a boat conformation. Rings C and F adopt envelope conformations.

Related literature

For the preparation, see: Song et al. (2007[Song, L., Liang, X. X., Chen, D. L., Jian, X. X. & Wang, F. P. (2007). Chem. Pharm. Bull. 55, 918-921.]). For other lycoctonine-type diterpenoid alkaloids, see: Tashkhodjaev & Sultankhodjaev (2009[Tashkhodjaev, B. & Sultankhodjaev, M. N. (2009). Acta Cryst. E65, o1543-o1544.]).

[Scheme 1]

Experimental

Crystal data
  • C26H39NO7

  • Mr = 477.58

  • Orthorhombic, P 21 21 21

  • a = 8.9444 (16) Å

  • b = 14.135 (3) Å

  • c = 19.112 (3) Å

  • V = 2416.4 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 133 K

  • 0.45 × 0.43 × 0.31 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 19113 measured reflections

  • 3122 independent reflections

  • 3020 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.080

  • S = 1.00

  • 3122 reflections

  • 312 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2002[Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, Anthriscifolcine A. (Song et al., 2007), C26H39NO7, is a norditerpenoid alkaloid and has a lycoctonine carbon skeleton. It contains four six-membered rings (A, B, D and E) and three five-membered rings (C, F and G). Its structure is similar with other lycoctonine-type diterpenoid alkaloids beside the appearance of new five-membered ring, which formed by a methylenedioxyl group at C-7 and C-8. (Tashkhodjaev & Sultankhodjaev, 2009). The rings A, B and E adopt a chair-conformation, while ring D adopts a boat-conformation with C-8, C-9, C-13 and C-16 in the same plane. The five-membered rings C and F adopt envelope conformations with C-9, C-10, C-12 and C-13 of ring C in the same plane, as well as C-5, C-6, C-7 and C-17 of ring F in the same plane. Ring G adopts a significant distorted five-membered ring. Since this type of norditerpenoid alkaloid is a well known skeleton mainly originated from Delphinium and Aconitum Linn with the absolute configuration of C(5) being R, the absolute structure of the chiral carbon centres of the title compound are identified as 1S, 4R, 5R, 6S, 7S, 8R, 9R, 10R, 11S, 13R, 14S, 16S and 17S.

At first, through one-dimensional and two-dimensional NMR analysis, we supposed the title compound that was isolated from Delphinium anthriscifolium var. majus is an isomer of Anthriscifolcines A (Song et al., 2007) for the strong 1H-1H COSY correlation of H-17 /H-5 seemingly indicative of the connection C(17)—C(5). On the other hand, comparison with the 13C NMR data reported by Dr Song, the chemical shift values of C-5, C-13, C-9 and C-10 differ from those of the one we got in D. A. var. majus. But X-ray crystal diffraction indicated that either the plane structure or its chirality was quite the same as Anthriscifolcine A as reported by Dr. Song. After detailed analysis of the HSQC and HMBC spectra, we found that the chemical shift values of C-5 with C-13, as well as C-9 with C-10 were wrongly exchanged in the literature.

Related literature top

For the preparation, see: Song et al. (2007). For other lycoctonine-type diterpenoid

alkaloids, see: Tashkhodjaev & Sultankhodjaev (2009).

Experimental top

The title compound was isolated from the EtOAc fraction of the leaves of D. A. var. majus by a known method (Song et al., 2007). Colourless single crystals were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 485–487 K).

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of Csp2—H = 0.93 Å with Uiso=1.2Ueq(C), and Csp3—H = 0.96 or 0.97 Å with Uiso=1.5Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering, showing displacement ellipsoids at the 30% probability level.
Anthriscifolcine A top
Crystal data top
C26H39NO7Dx = 1.313 Mg m3
Mr = 477.58Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8028 reflections
a = 8.9444 (16) Åθ = 3.1–27.5°
b = 14.135 (3) ŵ = 0.09 mm1
c = 19.112 (3) ÅT = 133 K
V = 2416.4 (7) Å3Block, colorless
Z = 40.45 × 0.43 × 0.31 mm
F(000) = 1032
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
3020 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.034
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1h = 1111
ϕ and ω scansk = 1818
19113 measured reflectionsl = 2124
3122 independent reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0431P)2 + 0.616P]
where P = (Fo2 + 2Fc2)/3
3122 reflections(Δ/σ)max < 0.001
312 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C26H39NO7V = 2416.4 (7) Å3
Mr = 477.58Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.9444 (16) ŵ = 0.09 mm1
b = 14.135 (3) ÅT = 133 K
c = 19.112 (3) Å0.45 × 0.43 × 0.31 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
3020 reflections with I > 2σ(I)
19113 measured reflectionsRint = 0.034
3122 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.00Δρmax = 0.24 e Å3
3122 reflectionsΔρmin = 0.17 e Å3
312 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
O10.30623 (14)0.49917 (9)0.71667 (6)0.0201 (3)
O20.44209 (14)0.42792 (9)0.62909 (7)0.0203 (3)
O30.72126 (15)0.46178 (8)0.91841 (6)0.0199 (3)
O40.36463 (14)0.26667 (8)0.70942 (7)0.0195 (3)
O50.13732 (16)0.30454 (11)0.66750 (8)0.0329 (3)
O70.77283 (14)0.39651 (9)0.59355 (6)0.0194 (3)
O80.85214 (15)0.60530 (9)0.65703 (7)0.0232 (3)
N10.37859 (17)0.49307 (10)0.87482 (8)0.0191 (3)
C10.6416 (2)0.37444 (12)0.90962 (9)0.0197 (4)
H10.71670.32200.91020.024*
C20.5383 (2)0.36093 (14)0.97290 (9)0.0258 (4)
H2A0.59830.33821.01300.031*
H2B0.49490.42290.98590.031*
C30.4122 (3)0.29143 (15)0.95935 (10)0.0314 (5)
H3A0.34200.29170.99940.038*
H3B0.45340.22680.95460.038*
C40.3289 (2)0.31858 (13)0.89248 (10)0.0253 (4)
H40.24260.27430.88670.030*
C50.4337 (2)0.30608 (12)0.82959 (9)0.0196 (4)
H50.46870.23910.82540.024*
C60.3504 (2)0.33800 (12)0.76349 (9)0.0183 (4)
H60.24200.34550.77520.022*
C70.4165 (2)0.43769 (12)0.74658 (9)0.0162 (3)
C80.53840 (19)0.43831 (12)0.69037 (9)0.0158 (3)
C90.6448 (2)0.35546 (11)0.70054 (8)0.0158 (3)
H90.59850.29510.68400.019*
C100.6892 (2)0.34851 (12)0.78001 (9)0.0168 (3)
H100.71350.28040.78860.020*
C110.5674 (2)0.37552 (11)0.83597 (9)0.0164 (3)
C120.84195 (19)0.40274 (13)0.78403 (9)0.0195 (4)
H12A0.83830.45210.82070.023*
H12B0.92440.35840.79500.023*
C130.8657 (2)0.44761 (12)0.71208 (9)0.0172 (3)
H130.97450.45530.70170.021*
C140.7952 (2)0.37223 (12)0.66496 (9)0.0169 (3)
H140.85620.31300.66760.020*
C150.6204 (2)0.53451 (12)0.68240 (9)0.0176 (3)
H15A0.61720.55220.63230.021*
H15B0.56170.58260.70820.021*
C160.7835 (2)0.54252 (12)0.70678 (9)0.0174 (3)
H160.78500.57350.75380.021*
C170.4825 (2)0.46807 (12)0.81829 (9)0.0160 (3)
H170.55580.52060.81120.019*
C190.2676 (2)0.42064 (14)0.89324 (11)0.0254 (4)
H19A0.18310.42480.86000.030*
H19B0.22820.43460.94050.030*
C210.3093 (2)0.58623 (13)0.86550 (10)0.0239 (4)
H21A0.22310.58030.83330.029*
H21B0.38260.62970.84370.029*
C220.2559 (3)0.62839 (16)0.93459 (11)0.0325 (5)
H22A0.33750.62650.96880.049*
H22B0.17100.59170.95220.049*
H22C0.22500.69410.92720.049*
C230.8432 (2)0.45474 (15)0.96600 (10)0.0280 (4)
H23A0.91640.40920.94800.042*
H23B0.80640.43331.01160.042*
H23C0.89070.51680.97110.042*
C240.3230 (2)0.49072 (13)0.64212 (9)0.0222 (4)
H24A0.22970.46610.62110.027*
H24B0.34480.55340.62130.027*
C250.9100 (2)0.40192 (14)0.55639 (9)0.0235 (4)
H25A0.96030.34040.55800.035*
H25B0.97410.45000.57790.035*
H25C0.89020.41910.50760.035*
C260.9849 (2)0.64858 (14)0.68263 (12)0.0309 (5)
H26A1.05870.59960.69380.046*
H26B0.96180.68490.72490.046*
H26C1.02560.69100.64680.046*
C270.2532 (2)0.26281 (12)0.66158 (10)0.0217 (4)
C280.2948 (3)0.20041 (14)0.60156 (10)0.0290 (4)
H28A0.21560.20240.56620.043*
H28B0.30740.13530.61820.043*
H28C0.38880.22260.58090.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0192 (6)0.0210 (6)0.0201 (6)0.0050 (5)0.0024 (5)0.0006 (5)
O20.0209 (6)0.0231 (6)0.0169 (6)0.0025 (5)0.0042 (5)0.0019 (5)
O30.0232 (6)0.0172 (6)0.0192 (6)0.0015 (5)0.0048 (5)0.0015 (5)
O40.0214 (6)0.0166 (6)0.0205 (6)0.0012 (5)0.0026 (5)0.0049 (5)
O50.0222 (7)0.0412 (8)0.0355 (8)0.0049 (7)0.0078 (6)0.0115 (7)
O70.0208 (6)0.0235 (6)0.0139 (6)0.0023 (5)0.0001 (5)0.0004 (5)
O80.0231 (6)0.0188 (6)0.0277 (7)0.0045 (6)0.0002 (6)0.0053 (5)
N10.0202 (7)0.0173 (7)0.0196 (7)0.0008 (6)0.0042 (6)0.0032 (6)
C10.0277 (9)0.0134 (7)0.0180 (8)0.0003 (7)0.0022 (8)0.0013 (6)
C20.0372 (11)0.0245 (9)0.0157 (9)0.0057 (9)0.0001 (8)0.0021 (7)
C30.0460 (12)0.0281 (10)0.0200 (9)0.0140 (10)0.0045 (9)0.0034 (8)
C40.0310 (10)0.0225 (9)0.0223 (9)0.0124 (8)0.0046 (8)0.0007 (7)
C50.0260 (9)0.0136 (8)0.0191 (9)0.0036 (7)0.0001 (7)0.0005 (6)
C60.0199 (8)0.0156 (8)0.0194 (8)0.0026 (7)0.0002 (7)0.0032 (7)
C70.0157 (8)0.0141 (7)0.0187 (8)0.0005 (7)0.0007 (7)0.0010 (6)
C80.0187 (8)0.0147 (8)0.0140 (8)0.0011 (7)0.0021 (7)0.0004 (6)
C90.0184 (8)0.0136 (7)0.0154 (8)0.0008 (7)0.0009 (7)0.0007 (6)
C100.0203 (8)0.0136 (7)0.0166 (8)0.0037 (7)0.0008 (7)0.0006 (6)
C110.0212 (8)0.0120 (7)0.0159 (8)0.0002 (7)0.0002 (7)0.0011 (6)
C120.0184 (8)0.0216 (8)0.0185 (8)0.0018 (7)0.0024 (7)0.0020 (7)
C130.0183 (7)0.0169 (8)0.0166 (8)0.0027 (7)0.0007 (7)0.0009 (6)
C140.0195 (8)0.0151 (8)0.0160 (8)0.0026 (7)0.0003 (7)0.0011 (6)
C150.0196 (9)0.0151 (8)0.0181 (8)0.0030 (7)0.0006 (7)0.0025 (6)
C160.0203 (8)0.0150 (8)0.0171 (8)0.0003 (7)0.0012 (7)0.0006 (6)
C170.0181 (8)0.0141 (7)0.0158 (8)0.0008 (7)0.0019 (7)0.0009 (6)
C190.0255 (9)0.0284 (10)0.0223 (10)0.0073 (8)0.0071 (8)0.0042 (7)
C210.0242 (9)0.0237 (9)0.0240 (9)0.0048 (8)0.0002 (8)0.0037 (7)
C220.0350 (11)0.0320 (11)0.0304 (11)0.0120 (9)0.0020 (9)0.0085 (8)
C230.0269 (10)0.0335 (10)0.0237 (9)0.0028 (9)0.0071 (8)0.0031 (8)
C240.0216 (9)0.0247 (9)0.0204 (9)0.0032 (8)0.0043 (7)0.0005 (7)
C250.0234 (8)0.0292 (10)0.0180 (9)0.0001 (8)0.0025 (7)0.0015 (7)
C260.0256 (10)0.0214 (9)0.0457 (12)0.0053 (8)0.0010 (9)0.0005 (9)
C270.0228 (9)0.0188 (8)0.0236 (9)0.0038 (8)0.0021 (7)0.0003 (7)
C280.0353 (11)0.0275 (10)0.0242 (10)0.0037 (9)0.0070 (9)0.0063 (8)
Geometric parameters (Å, º) top
O1—C71.433 (2)C10—C121.568 (2)
O1—C241.438 (2)C10—C111.574 (2)
O2—C241.409 (2)C10—H101.0000
O2—C81.461 (2)C11—C171.550 (2)
O3—C231.424 (2)C12—C131.529 (2)
O3—C11.435 (2)C12—H12A0.9900
O4—C271.354 (2)C12—H12B0.9900
O4—C61.449 (2)C13—C141.531 (2)
O5—C271.198 (2)C13—C161.533 (2)
O7—C251.419 (2)C13—H131.0000
O7—C141.422 (2)C14—H141.0000
O8—C261.422 (2)C15—C161.536 (2)
O8—C161.438 (2)C15—H15A0.9900
N1—C211.466 (2)C15—H15B0.9900
N1—C171.468 (2)C16—H161.0000
N1—C191.469 (2)C17—H171.0000
C1—C21.534 (3)C19—H19A0.9900
C1—C111.557 (2)C19—H19B0.9900
C1—H11.0000C21—C221.525 (3)
C2—C31.518 (3)C21—H21A0.9900
C2—H2A0.9900C21—H21B0.9900
C2—H2B0.9900C22—H22A0.9800
C3—C41.528 (3)C22—H22B0.9800
C3—H3A0.9900C22—H22C0.9800
C3—H3B0.9900C23—H23A0.9800
C4—C51.534 (3)C23—H23B0.9800
C4—C191.543 (3)C23—H23C0.9800
C4—H41.0000C24—H24A0.9900
C5—C61.534 (2)C24—H24B0.9900
C5—C111.552 (2)C25—H25A0.9800
C5—H51.0000C25—H25B0.9800
C6—C71.562 (2)C25—H25C0.9800
C6—H61.0000C26—H26A0.9800
C7—C81.531 (2)C26—H26B0.9800
C7—C171.553 (2)C26—H26C0.9800
C8—C91.522 (2)C27—C281.494 (3)
C8—C151.552 (2)C28—H28A0.9800
C9—C141.526 (2)C28—H28B0.9800
C9—C101.573 (2)C28—H28C0.9800
C9—H91.0000
C7—O1—C24105.84 (13)C12—C13—C14100.56 (14)
C24—O2—C8103.92 (13)C12—C13—C16110.85 (14)
C23—O3—C1113.26 (14)C14—C13—C16111.90 (14)
C27—O4—C6116.41 (14)C12—C13—H13111.0
C25—O7—C14111.81 (14)C14—C13—H13111.0
C26—O8—C16113.22 (15)C16—C13—H13111.0
C21—N1—C17113.23 (14)O7—C14—C9109.93 (14)
C21—N1—C19111.68 (15)O7—C14—C13117.06 (14)
C17—N1—C19115.87 (14)C9—C14—C13102.05 (13)
O3—C1—C2108.29 (14)O7—C14—H14109.1
O3—C1—C11108.02 (13)C9—C14—H14109.1
C2—C1—C11117.18 (16)C13—C14—H14109.1
O3—C1—H1107.7C16—C15—C8118.92 (14)
C2—C1—H1107.7C16—C15—H15A107.6
C11—C1—H1107.7C8—C15—H15A107.6
C3—C2—C1113.19 (16)C16—C15—H15B107.6
C3—C2—H2A108.9C8—C15—H15B107.6
C1—C2—H2A108.9H15A—C15—H15B107.0
C3—C2—H2B108.9O8—C16—C13112.28 (14)
C1—C2—H2B108.9O8—C16—C15104.50 (14)
H2A—C2—H2B107.8C13—C16—C15114.26 (14)
C2—C3—C4110.01 (16)O8—C16—H16108.5
C2—C3—H3A109.7C13—C16—H16108.5
C4—C3—H3A109.7C15—C16—H16108.5
C2—C3—H3B109.7N1—C17—C11110.66 (14)
C4—C3—H3B109.7N1—C17—C7118.36 (14)
H3A—C3—H3B108.2C11—C17—C798.35 (13)
C3—C4—C5109.20 (17)N1—C17—H17109.6
C3—C4—C19113.58 (17)C11—C17—H17109.6
C5—C4—C19109.38 (14)C7—C17—H17109.6
C3—C4—H4108.2N1—C19—C4114.17 (16)
C5—C4—H4108.2N1—C19—H19A108.7
C19—C4—H4108.2C4—C19—H19A108.7
C4—C5—C6108.35 (15)N1—C19—H19B108.7
C4—C5—C11109.64 (14)C4—C19—H19B108.7
C6—C5—C11104.64 (13)H19A—C19—H19B107.6
C4—C5—H5111.3N1—C21—C22112.21 (16)
C6—C5—H5111.3N1—C21—H21A109.2
C11—C5—H5111.3C22—C21—H21A109.2
O4—C6—C5109.86 (14)N1—C21—H21B109.2
O4—C6—C7116.54 (14)C22—C21—H21B109.2
C5—C6—C7104.58 (14)H21A—C21—H21B107.9
O4—C6—H6108.5C21—C22—H22A109.5
C5—C6—H6108.5C21—C22—H22B109.5
C7—C6—H6108.5H22A—C22—H22B109.5
O1—C7—C8101.93 (13)C21—C22—H22C109.5
O1—C7—C17116.49 (14)H22A—C22—H22C109.5
C8—C7—C17110.30 (14)H22B—C22—H22C109.5
O1—C7—C6111.66 (14)O3—C23—H23A109.5
C8—C7—C6114.84 (14)O3—C23—H23B109.5
C17—C7—C6102.17 (13)H23A—C23—H23B109.5
O2—C8—C9113.19 (14)O3—C23—H23C109.5
O2—C8—C798.17 (13)H23A—C23—H23C109.5
C9—C8—C7110.58 (14)H23B—C23—H23C109.5
O2—C8—C15106.73 (13)O2—C24—O1107.87 (14)
C9—C8—C15113.04 (14)O2—C24—H24A110.1
C7—C8—C15114.22 (14)O1—C24—H24A110.1
C8—C9—C14112.02 (14)O2—C24—H24B110.1
C8—C9—C10109.23 (13)O1—C24—H24B110.1
C14—C9—C10102.55 (14)H24A—C24—H24B108.4
C8—C9—H9110.9O7—C25—H25A109.5
C14—C9—H9110.9O7—C25—H25B109.5
C10—C9—H9110.9H25A—C25—H25B109.5
C12—C10—C9103.69 (13)O7—C25—H25C109.5
C12—C10—C11116.83 (14)H25A—C25—H25C109.5
C9—C10—C11117.78 (14)H25B—C25—H25C109.5
C12—C10—H10105.8O8—C26—H26A109.5
C9—C10—H10105.8O8—C26—H26B109.5
C11—C10—H10105.8H26A—C26—H26B109.5
C17—C11—C598.02 (14)O8—C26—H26C109.5
C17—C11—C1114.49 (14)H26A—C26—H26C109.5
C5—C11—C1113.19 (14)H26B—C26—H26C109.5
C17—C11—C10113.31 (13)O5—C27—O4123.60 (17)
C5—C11—C10109.07 (13)O5—C27—C28125.38 (18)
C1—C11—C10108.45 (14)O4—C27—C28111.02 (16)
C13—C12—C10106.23 (14)C27—C28—H28A109.5
C13—C12—H12A110.5C27—C28—H28B109.5
C10—C12—H12A110.5H28A—C28—H28B109.5
C13—C12—H12B110.5C27—C28—H28C109.5
C10—C12—H12B110.5H28A—C28—H28C109.5
H12A—C12—H12B108.7H28B—C28—H28C109.5
C23—O3—C1—C278.45 (18)C2—C1—C11—C10157.24 (15)
C23—O3—C1—C11153.71 (15)C12—C10—C11—C1779.16 (18)
O3—C1—C2—C3160.33 (16)C9—C10—C11—C1745.3 (2)
C11—C1—C2—C337.9 (2)C12—C10—C11—C5172.79 (14)
C1—C2—C3—C452.0 (2)C9—C10—C11—C562.72 (18)
C2—C3—C4—C566.2 (2)C12—C10—C11—C149.12 (18)
C2—C3—C4—C1956.2 (2)C9—C10—C11—C1173.60 (14)
C3—C4—C5—C6177.44 (15)C9—C10—C12—C137.26 (17)
C19—C4—C5—C652.58 (19)C11—C10—C12—C13124.09 (15)
C3—C4—C5—C1163.79 (18)C10—C12—C13—C1434.41 (16)
C19—C4—C5—C1161.07 (19)C10—C12—C13—C1684.09 (17)
C27—O4—C6—C5153.01 (15)C25—O7—C14—C9173.13 (14)
C27—O4—C6—C788.33 (19)C25—O7—C14—C1371.10 (19)
C4—C5—C6—O4130.98 (14)C8—C9—C14—O753.00 (18)
C11—C5—C6—O4112.10 (15)C10—C9—C14—O7170.00 (13)
C4—C5—C6—C7103.22 (16)C8—C9—C14—C1371.91 (16)
C11—C5—C6—C713.69 (17)C10—C9—C14—C1345.09 (15)
C24—O1—C7—C828.66 (17)C12—C13—C14—O7169.43 (15)
C24—O1—C7—C17148.75 (15)C16—C13—C14—O751.7 (2)
C24—O1—C7—C694.42 (16)C12—C13—C14—C949.40 (15)
O4—C6—C7—O192.28 (17)C16—C13—C14—C968.33 (17)
C5—C6—C7—O1146.23 (14)O2—C8—C15—C16143.22 (15)
O4—C6—C7—C823.1 (2)C9—C8—C15—C1618.1 (2)
C5—C6—C7—C898.38 (16)C7—C8—C15—C16109.45 (17)
O4—C6—C7—C17142.51 (15)C26—O8—C16—C1376.69 (18)
C5—C6—C7—C1721.02 (16)C26—O8—C16—C15158.94 (14)
C24—O2—C8—C9160.42 (14)C12—C13—C16—O8153.62 (14)
C24—O2—C8—C743.82 (15)C14—C13—C16—O894.99 (17)
C24—O2—C8—C1574.60 (16)C12—C13—C16—C1587.59 (18)
O1—C7—C8—O244.26 (15)C14—C13—C16—C1523.8 (2)
C17—C7—C8—O2168.60 (13)C8—C15—C16—O8144.03 (15)
C6—C7—C8—O276.63 (16)C8—C15—C16—C1320.9 (2)
O1—C7—C8—C9162.87 (13)C21—N1—C17—C11172.51 (14)
C17—C7—C8—C972.79 (17)C19—N1—C17—C1156.6 (2)
C6—C7—C8—C941.98 (19)C21—N1—C17—C775.16 (19)
O1—C7—C8—C1568.29 (17)C19—N1—C17—C755.8 (2)
C17—C7—C8—C1556.06 (18)C5—C11—C17—N169.33 (16)
C6—C7—C8—C15170.82 (14)C1—C11—C17—N150.74 (19)
O2—C8—C9—C1492.06 (17)C10—C11—C17—N1175.83 (14)
C7—C8—C9—C14158.92 (14)C5—C11—C17—C755.31 (14)
C15—C8—C9—C1429.44 (19)C1—C11—C17—C7175.38 (14)
O2—C8—C9—C10155.03 (14)C10—C11—C17—C759.53 (16)
C7—C8—C9—C1046.01 (18)O1—C7—C17—N150.6 (2)
C15—C8—C9—C1083.48 (17)C8—C7—C17—N1166.10 (14)
C8—C9—C10—C1296.06 (16)C6—C7—C17—N171.36 (17)
C14—C9—C10—C1222.92 (16)O1—C7—C17—C11169.57 (14)
C8—C9—C10—C1134.7 (2)C8—C7—C17—C1174.93 (15)
C14—C9—C10—C11153.71 (14)C6—C7—C17—C1147.61 (15)
C4—C5—C11—C1773.03 (16)C21—N1—C19—C4170.95 (16)
C6—C5—C11—C1743.00 (16)C17—N1—C19—C439.3 (2)
C4—C5—C11—C148.02 (19)C3—C4—C19—N181.9 (2)
C6—C5—C11—C1164.04 (14)C5—C4—C19—N140.3 (2)
C4—C5—C11—C10168.83 (14)C17—N1—C21—C22156.45 (16)
C6—C5—C11—C1075.14 (16)C19—N1—C21—C2270.6 (2)
O3—C1—C11—C1747.39 (19)C8—O2—C24—O128.12 (17)
C2—C1—C11—C1775.15 (19)C7—O1—C24—O21.39 (18)
O3—C1—C11—C5158.61 (14)C6—O4—C27—O511.0 (3)
C2—C1—C11—C536.1 (2)C6—O4—C27—C28168.90 (15)
O3—C1—C11—C1080.22 (16)

Experimental details

Crystal data
Chemical formulaC26H39NO7
Mr477.58
Crystal system, space groupOrthorhombic, P212121
Temperature (K)133
a, b, c (Å)8.9444 (16), 14.135 (3), 19.112 (3)
V3)2416.4 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.45 × 0.43 × 0.31
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19113, 3122, 3020
Rint0.034
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.080, 1.00
No. of reflections3122
No. of parameters312
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.17

Computer programs: CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Gangdong Provincial Natural Science Foundation of China (No. 8251064201000001).

References

First citationRigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSong, L., Liang, X. X., Chen, D. L., Jian, X. X. & Wang, F. P. (2007). Chem. Pharm. Bull. 55, 918–921.  Web of Science CrossRef PubMed CAS Google Scholar
First citationTashkhodjaev, B. & Sultankhodjaev, M. N. (2009). Acta Cryst. E65, o1543–o1544.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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