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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1394.
Published online 2008 July 5. doi:  10.1107/S1600536808019223
PMCID: PMC2962025

(1α,2β,3α,7α,11α,13β)-1,3,11-Triacet­oxy-2,13-bis­(benz­yloxy)-7-hydr­oxy-21-methyl-N,19-secohetisan-19-al

Abstract

The title compound (delgradine), C41H43NO12, is a hetisine-type C20-diterpenoid alkaloid, isolated from the roots of Aconitum carmichaeli Debx. In the crystal structure, the mol­ecule assumes an U-shaped conformation, the terminal benzene rings being approximately parallel and partially overlapped with each other. The mol­ecule contains eight alicyclic and heterocyclic rings. Cyclo­hexane rings A and B adopt similar chair conformations; the six-membered rings C, D and E form a bicyclo­[2.2.2]octane system with a boat conformation for each six-membered ring, the six-membered heterocyclic ring F has a screw-boat conformation and both of the five-membered rings G and H have envelope conformations. The crystal structure contains inter­molecular O—H(...)O hydrogen bonding.

Related literature

For related literature, see: Deng et al. (1992 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1394-scheme1.jpg

Experimental

Crystal data

  • C41H43NO12
  • M r = 741.76
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1394-efi1.jpg
  • a = 19.892 (4) Å
  • b = 11.307 (5) Å
  • c = 16.825 (5) Å
  • β = 91.07 (2)°
  • V = 3784 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 291 (2) K
  • 0.42 × 0.40 × 0.36 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: none
  • 4309 measured reflections
  • 3705 independent reflections
  • 2282 reflections with I > 2σ(I)
  • R int = 0.018
  • 3 standard reflections every 300 reflections intensity decay: 2.6%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.130
  • S = 1.01
  • 3705 reflections
  • 498 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 [triangle]); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019223/xu2424sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019223/xu2424Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This project was supported by Mianyang Normal University Scientific Research Fund (MY2006003) and a grant from Sichuan Provincial Department of Education, China (2005 A165).

supplementary crystallographic information

Comment

The diterpenoid alkaloid, delgradine, was previously isolated from Delphinium grandiflorum L. (Deng et al., 1992), and its structure was established from the spectroscopic data. In our recent investigation, it was isolated from Aconitum carmichaeli Debx, and its crystal structure was determined.

The molecular structure of the title compound is shown in Fig. 1. The molecule of the title compound assumes an U-shaped conformation, with terminal benzene rings being approximately parallel and partially overlapped to each other. The molecule contains eight alicyclic and heterocyclic rings. Cyclohexane rings A (C1/C2/C3/C4/C5/C10) and B (C5/C6/C7/C8/C9/C10) adopt chair conformations; six-membered rings C (C8/C9/C11/C12/C13/C14), D (C8/C9/C11/C12/C15/C16) and E (C8/C12/C13/C14/C15/C16) form a bicycle [2.2.2] octane system with the boat conformation for each six-membered ring C, D and E; the six-membered heterocyclic ring F (C6/C7/C8/C14/C20/N1) adopts a screw-boat conformation; while the five-membered rings G (C5/C6/C10/C20/N1) and H (C8/C9/C10/C14/C20) adopt the same envelope conformation.

The crystal structure contains intermolecular O—H···O hydrogen bond between the hydroxy group and aldehyde O atom (Table 1).

Experimental

The title compound was isolated from the roots of Aconitum carmichaeli Debx and crystals suitable for X-ray structure analysis were obtained by slow evaporation from an acetone solution at room temperature.

Refinement

H atoms were located geometrically with C—H distance of 0.93–0.98 Å, and refined using a riding model with Uiso(H) = 1.2Ueq(C). The absolute configuration has not been determined for the structure.

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability displacement ellipsoids for non-H atoms. H atoms have been omitted for clarity.

Crystal data

C41H43NO12F000 = 1568
Mr = 741.76Dx = 1.302 Mg m3
Monoclinic, C2Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 55 reflections
a = 19.892 (4) Åθ = 4.7–7.6º
b = 11.307 (5) ŵ = 0.10 mm1
c = 16.825 (5) ÅT = 291 (2) K
β = 91.07 (2)ºBlock, colourless
V = 3784 (2) Å30.42 × 0.40 × 0.36 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.018
Radiation source: fine-focus sealed tubeθmax = 25.5º
Monochromator: graphiteθmin = 1.2º
T = 291(2) Kh = −6→24
ω/2θ scansk = −13→0
Absorption correction: nonel = −20→20
4309 measured reflections3 standard reflections
3705 independent reflections every 300 reflections
2282 reflections with I > 2σ(I) intensity decay: 2.6%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.130  w = 1/[σ2(Fo2) + (0.0734P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3705 reflectionsΔρmax = 0.19 e Å3
498 parametersΔρmin = −0.20 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0010 (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 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)

xyzUiso*/Ueq
N10.10745 (17)0.5052 (3)0.8921 (2)0.0427 (9)
O1A0.21024 (15)0.8335 (3)0.78232 (16)0.0456 (8)
O1B0.26263 (18)0.8288 (3)0.6655 (2)0.0639 (10)
O2A0.12403 (14)0.5813 (3)0.69392 (16)0.0449 (7)
O2B0.1133 (2)0.6310 (4)0.5646 (2)0.0872 (13)
O3A0.01724 (15)0.7482 (3)0.69724 (18)0.0593 (9)
O3B0.0463 (4)0.9136 (5)0.6367 (3)0.128 (2)
O70.14601 (16)0.5003 (3)1.06651 (19)0.0573 (9)
H7A0.11000.50651.08910.069*
O11A0.33185 (14)0.7260 (3)0.82500 (17)0.0465 (8)
O11B0.43602 (17)0.7575 (4)0.8731 (2)0.0794 (12)
O13A0.30189 (15)0.4752 (3)0.80593 (17)0.0472 (8)
O13B0.2702 (2)0.2863 (3)0.7952 (2)0.0871 (13)
O19−0.03068 (16)0.5601 (4)0.8561 (2)0.0716 (11)
C10.1948 (2)0.7076 (4)0.7724 (2)0.0378 (10)
H10.23320.66680.74920.045*
C20.1350 (2)0.7038 (4)0.7150 (3)0.0437 (11)
H20.14620.74800.66700.052*
C30.0741 (2)0.7595 (4)0.7516 (2)0.0463 (11)
H30.08340.84400.75860.056*
C40.0528 (2)0.7102 (4)0.8317 (3)0.0471 (11)
C50.1138 (2)0.7027 (4)0.8903 (2)0.0399 (10)
H50.12000.77770.91870.048*
C60.1016 (2)0.6019 (5)0.9487 (3)0.0482 (12)
H60.05620.60590.97020.058*
C70.1547 (2)0.5984 (4)1.0151 (2)0.0439 (11)
H70.15190.67141.04620.053*
C80.2248 (2)0.5890 (4)0.9808 (2)0.0383 (10)
C90.2367 (2)0.6898 (4)0.9200 (2)0.0374 (10)
H90.22530.76550.94470.045*
C100.1821 (2)0.6595 (4)0.8551 (2)0.0361 (10)
C110.3135 (2)0.6881 (4)0.9037 (3)0.0412 (11)
H110.33420.74470.94090.049*
C120.3439 (2)0.5665 (4)0.9241 (3)0.0462 (12)
H120.38930.55990.90280.055*
C130.2999 (2)0.4682 (4)0.8923 (3)0.0449 (11)
H130.31820.39190.90990.054*
C140.2277 (2)0.4820 (4)0.9232 (2)0.0393 (10)
H140.21330.40950.94990.047*
C150.2779 (2)0.5792 (5)1.0474 (2)0.0485 (12)
H15A0.27800.65101.07900.058*
H15B0.26700.51351.08190.058*
C160.3465 (2)0.5605 (4)1.0133 (3)0.0489 (12)
C170.4016 (3)0.5488 (7)1.0559 (4)0.086 (2)
H17A0.44290.54371.03110.103*
H17B0.39950.54571.11100.103*
C18−0.0002 (2)0.7940 (5)0.8672 (3)0.0626 (14)
H18A−0.03770.80120.83070.075*
H18B0.01950.87040.87610.075*
H18C−0.01530.76230.91670.075*
C190.0189 (2)0.5891 (5)0.8198 (3)0.0542 (12)
H190.03700.53630.78360.065*
C200.1745 (2)0.5210 (4)0.8599 (3)0.0402 (10)
H200.18000.48180.80850.048*
C210.0857 (3)0.3858 (5)0.9132 (3)0.0620 (14)
H21A0.03790.38560.92080.074*
H21B0.10820.36160.96150.074*
H21C0.09660.33210.87120.074*
C220.2639 (4)1.0078 (5)0.7406 (4)0.092 (2)
H22A0.28961.03900.69770.110*
H22B0.28991.01230.78910.110*
H22C0.22341.05310.74590.110*
C230.2465 (3)0.8829 (5)0.7239 (3)0.0537 (13)
C240.0951 (3)0.3908 (6)0.5239 (4)0.0798 (18)
H240.09610.44480.48230.096*
C250.0857 (4)0.2712 (8)0.5086 (5)0.105 (2)
H250.08150.24500.45640.126*
C260.0826 (3)0.1918 (7)0.5692 (5)0.097 (2)
H260.07600.11200.55800.116*
C270.0890 (3)0.2280 (6)0.6458 (4)0.0789 (18)
H270.08670.17350.68700.095*
C280.0991 (3)0.3476 (5)0.6623 (4)0.0633 (15)
H280.10320.37270.71480.076*
C290.1030 (2)0.4288 (5)0.6018 (3)0.0578 (14)
C300.1133 (2)0.5557 (5)0.6152 (3)0.0539 (13)
C31−0.0498 (3)0.8056 (9)0.5893 (4)0.123 (3)
H31A−0.04280.73020.56470.148*
H31B−0.05460.86530.54900.148*
H31C−0.08980.80280.62030.148*
C320.0092 (3)0.8346 (8)0.6421 (4)0.0823 (19)
C330.4142 (3)0.7951 (8)0.7368 (4)0.098 (2)
H33A0.43890.73360.71110.117*
H33B0.44100.86560.73940.117*
H33C0.37350.81080.70710.117*
C340.3974 (3)0.7571 (5)0.8182 (3)0.0577 (13)
C350.2721 (3)0.3096 (6)0.6249 (3)0.0702 (16)
H350.26020.23580.64470.084*
C360.2733 (3)0.3267 (7)0.5437 (4)0.0825 (19)
H360.26340.26470.50910.099*
C370.2888 (3)0.4340 (8)0.5155 (4)0.0827 (19)
H370.29010.44610.46080.099*
C380.3029 (3)0.5266 (6)0.5663 (3)0.0768 (17)
H380.31210.60130.54620.092*
C390.3033 (3)0.5082 (5)0.6456 (3)0.0607 (14)
H390.31400.57050.67960.073*
C400.2881 (2)0.3992 (5)0.6772 (3)0.0494 (12)
C410.2861 (3)0.3773 (5)0.7645 (3)0.0528 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.039 (2)0.042 (2)0.047 (2)−0.0067 (17)0.0019 (17)0.0073 (19)
O1A0.0632 (19)0.0374 (17)0.0361 (16)−0.0078 (16)−0.0019 (15)0.0036 (15)
O1B0.080 (2)0.070 (2)0.0413 (19)−0.020 (2)0.0041 (17)0.0045 (19)
O2A0.0510 (17)0.0457 (19)0.0379 (17)−0.0074 (15)−0.0017 (13)0.0004 (15)
O2B0.142 (4)0.078 (3)0.042 (2)−0.011 (3)−0.015 (2)0.004 (2)
O3A0.0490 (18)0.080 (3)0.0489 (19)0.0077 (18)−0.0111 (15)0.006 (2)
O3B0.168 (6)0.104 (4)0.111 (4)0.003 (4)−0.041 (4)0.053 (4)
O70.0489 (19)0.074 (2)0.049 (2)0.0051 (18)0.0111 (15)0.0233 (18)
O11A0.0421 (16)0.0542 (19)0.0433 (18)−0.0109 (15)0.0012 (14)0.0066 (15)
O11B0.051 (2)0.104 (3)0.083 (3)−0.031 (2)−0.009 (2)0.005 (3)
O13A0.0613 (19)0.0440 (19)0.0367 (17)−0.0014 (16)0.0077 (14)−0.0043 (15)
O13B0.156 (4)0.042 (2)0.064 (2)−0.020 (3)0.016 (2)−0.001 (2)
O190.0430 (18)0.092 (3)0.080 (2)−0.0066 (19)0.0115 (18)0.017 (2)
C10.043 (2)0.038 (2)0.032 (2)−0.001 (2)0.0035 (19)0.000 (2)
C20.047 (2)0.041 (3)0.042 (2)−0.004 (2)0.000 (2)0.006 (2)
C30.045 (2)0.046 (3)0.048 (3)0.008 (2)−0.003 (2)0.007 (2)
C40.042 (2)0.048 (3)0.051 (3)0.006 (2)0.002 (2)0.001 (2)
C50.044 (2)0.041 (2)0.035 (2)−0.003 (2)0.002 (2)0.005 (2)
C60.034 (2)0.066 (3)0.045 (3)0.002 (2)0.007 (2)0.006 (3)
C70.052 (3)0.047 (3)0.033 (2)0.006 (2)0.003 (2)0.008 (2)
C80.042 (2)0.042 (2)0.031 (2)0.004 (2)0.0007 (18)0.001 (2)
C90.041 (2)0.037 (2)0.034 (2)−0.002 (2)0.0027 (19)−0.005 (2)
C100.039 (2)0.035 (2)0.035 (2)−0.0017 (18)0.0003 (19)−0.0051 (19)
C110.047 (2)0.045 (3)0.031 (2)−0.008 (2)−0.001 (2)0.001 (2)
C120.041 (2)0.056 (3)0.042 (3)0.000 (2)0.004 (2)0.001 (2)
C130.053 (3)0.043 (3)0.039 (3)0.004 (2)0.002 (2)0.002 (2)
C140.044 (2)0.038 (2)0.036 (2)−0.003 (2)0.0031 (19)0.004 (2)
C150.050 (3)0.059 (3)0.036 (2)−0.001 (3)−0.002 (2)0.000 (3)
C160.052 (3)0.055 (3)0.039 (2)0.002 (2)−0.002 (2)0.006 (2)
C170.057 (3)0.138 (6)0.063 (4)0.006 (4)−0.008 (3)0.020 (4)
C180.053 (3)0.079 (4)0.056 (3)0.017 (3)0.002 (2)−0.002 (3)
C190.042 (3)0.067 (3)0.054 (3)0.000 (3)0.002 (2)0.004 (3)
C200.049 (3)0.038 (3)0.034 (2)−0.005 (2)−0.002 (2)0.006 (2)
C210.061 (3)0.056 (3)0.069 (3)−0.022 (3)−0.007 (3)0.019 (3)
C220.156 (7)0.053 (4)0.066 (4)−0.032 (4)0.017 (4)0.003 (3)
C230.077 (3)0.048 (3)0.036 (3)−0.018 (3)−0.001 (2)0.010 (3)
C240.089 (4)0.085 (5)0.065 (4)−0.008 (4)−0.007 (3)−0.018 (3)
C250.129 (6)0.095 (6)0.091 (5)−0.015 (5)−0.009 (4)−0.045 (5)
C260.096 (5)0.067 (5)0.128 (7)−0.007 (4)0.012 (5)−0.040 (5)
C270.071 (4)0.062 (4)0.103 (5)−0.005 (3)0.012 (3)−0.018 (4)
C280.061 (3)0.062 (4)0.067 (4)−0.005 (3)0.002 (3)−0.009 (3)
C290.048 (3)0.066 (4)0.059 (3)−0.005 (3)−0.003 (2)−0.011 (3)
C300.054 (3)0.063 (4)0.044 (3)−0.006 (3)−0.006 (2)−0.002 (3)
C310.077 (4)0.222 (10)0.070 (4)0.043 (6)−0.015 (3)0.011 (6)
C320.085 (4)0.100 (5)0.061 (4)0.027 (4)−0.014 (3)0.013 (4)
C330.066 (4)0.144 (7)0.085 (4)−0.027 (4)0.021 (3)0.029 (5)
C340.051 (3)0.058 (3)0.064 (3)−0.021 (3)0.009 (3)0.005 (3)
C350.073 (4)0.067 (4)0.071 (4)−0.008 (3)0.012 (3)−0.020 (3)
C360.083 (4)0.100 (6)0.064 (4)−0.010 (4)−0.003 (3)−0.033 (4)
C370.083 (4)0.116 (6)0.049 (3)0.009 (4)−0.007 (3)−0.010 (4)
C380.091 (4)0.085 (5)0.055 (4)0.002 (4)0.009 (3)0.016 (4)
C390.070 (3)0.064 (4)0.048 (3)0.007 (3)0.010 (3)−0.004 (3)
C400.054 (3)0.052 (3)0.042 (3)−0.001 (2)0.009 (2)−0.009 (2)
C410.063 (3)0.043 (3)0.053 (3)−0.002 (3)0.014 (2)−0.007 (3)

Geometric parameters (Å, °)

N1—C61.456 (6)C14—C201.551 (6)
N1—C201.459 (5)C14—H140.9800
N1—C211.464 (6)C15—C161.506 (6)
O1A—C231.352 (5)C15—H15A0.9700
O1A—C11.464 (5)C15—H15B0.9700
O1B—C231.206 (6)C16—C171.304 (7)
O2A—C301.369 (5)C17—H17A0.9300
O2A—C21.445 (6)C17—H17B0.9300
O2B—C301.203 (6)C18—H18A0.9600
O3A—C321.354 (8)C18—H18B0.9600
O3A—C31.447 (5)C18—H18C0.9600
O3B—C321.165 (9)C19—H190.9300
O7—C71.420 (5)C20—H200.9800
O7—H7A0.8200C21—H21A0.9600
O11A—C341.358 (5)C21—H21B0.9600
O11A—C111.445 (5)C21—H21C0.9600
O11B—C341.190 (6)C22—C231.480 (8)
O13A—C411.342 (6)C22—H22A0.9600
O13A—C131.457 (5)C22—H22B0.9600
O13B—C411.197 (6)C22—H22C0.9600
O19—C191.216 (5)C24—C291.385 (8)
C1—C101.519 (6)C24—C251.389 (11)
C1—C21.520 (6)C24—H240.9300
C1—H10.9800C25—C261.360 (11)
C2—C31.506 (6)C25—H250.9300
C2—H20.9800C26—C271.356 (9)
C3—C41.525 (6)C26—H260.9300
C3—H30.9800C27—C281.394 (8)
C4—C191.538 (8)C27—H270.9300
C4—C181.545 (7)C28—C291.374 (8)
C4—C51.552 (6)C28—H280.9300
C5—C61.528 (7)C29—C301.467 (8)
C5—C101.570 (6)C31—C321.494 (9)
C5—H50.9800C31—H31A0.9600
C6—C71.524 (6)C31—H31B0.9600
C6—H60.9800C31—H31C0.9600
C7—C81.522 (6)C33—C341.479 (7)
C7—H70.9800C33—H33A0.9600
C8—C151.529 (6)C33—H33B0.9600
C8—C141.552 (6)C33—H33C0.9600
C8—C91.553 (6)C35—C401.376 (7)
C9—C111.557 (6)C35—C361.381 (8)
C9—C101.564 (6)C35—H350.9300
C9—H90.9800C36—C371.341 (10)
C10—C201.576 (6)C36—H360.9300
C11—C121.538 (7)C37—C381.377 (9)
C11—H110.9800C37—H370.9300
C12—C161.501 (6)C38—C391.350 (7)
C12—C131.507 (6)C38—H380.9300
C12—H120.9800C39—C401.378 (7)
C13—C141.544 (6)C39—H390.9300
C13—H130.9800C40—C411.490 (7)
C6—N1—C20103.7 (3)H15A—C15—H15B108.1
C6—N1—C21120.4 (4)C17—C16—C12124.5 (5)
C20—N1—C21118.7 (4)C17—C16—C15124.2 (4)
C23—O1A—C1115.6 (4)C12—C16—C15111.1 (4)
C30—O2A—C2117.4 (4)C16—C17—H17A120.0
C32—O3A—C3116.8 (5)C16—C17—H17B120.0
C7—O7—H7A109.5H17A—C17—H17B120.0
C34—O11A—C11114.4 (3)C4—C18—H18A109.5
C41—O13A—C13117.6 (4)C4—C18—H18B109.5
O1A—C1—C10106.4 (3)H18A—C18—H18B109.5
O1A—C1—C2105.1 (3)C4—C18—H18C109.5
C10—C1—C2115.4 (4)H18A—C18—H18C109.5
O1A—C1—H1109.9H18B—C18—H18C109.5
C10—C1—H1109.9O19—C19—C4122.2 (5)
C2—C1—H1109.9O19—C19—H19118.9
O2A—C2—C3112.5 (4)C4—C19—H19118.9
O2A—C2—C1107.2 (3)N1—C20—C14109.1 (3)
C3—C2—C1110.8 (4)N1—C20—C10103.3 (4)
O2A—C2—H2108.7C14—C20—C10104.6 (3)
C3—C2—H2108.7N1—C20—H20113.0
C1—C2—H2108.7C14—C20—H20113.0
O3A—C3—C2109.2 (3)C10—C20—H20113.0
O3A—C3—C4107.5 (3)N1—C21—H21A109.5
C2—C3—C4116.5 (4)N1—C21—H21B109.5
O3A—C3—H3107.8H21A—C21—H21B109.5
C2—C3—H3107.8N1—C21—H21C109.5
C4—C3—H3107.8H21A—C21—H21C109.5
C3—C4—C19109.8 (4)H21B—C21—H21C109.5
C3—C4—C18108.6 (4)C23—C22—H22A109.5
C19—C4—C18107.2 (4)C23—C22—H22B109.5
C3—C4—C5110.8 (4)H22A—C22—H22B109.5
C19—C4—C5111.7 (4)C23—C22—H22C109.5
C18—C4—C5108.6 (4)H22A—C22—H22C109.5
C6—C5—C4108.5 (4)H22B—C22—H22C109.5
C6—C5—C1099.2 (3)O1B—C23—O1A122.5 (4)
C4—C5—C10116.7 (4)O1B—C23—C22125.1 (5)
C6—C5—H5110.6O1A—C23—C22112.4 (5)
C4—C5—H5110.6C29—C24—C25119.3 (7)
C10—C5—H5110.6C29—C24—H24120.3
N1—C6—C7113.4 (4)C25—C24—H24120.3
N1—C6—C597.1 (3)C26—C25—C24120.8 (7)
C7—C6—C5111.9 (4)C26—C25—H25119.6
N1—C6—H6111.2C24—C25—H25119.6
C7—C6—H6111.2C27—C26—C25120.5 (7)
C5—C6—H6111.2C27—C26—H26119.7
O7—C7—C8107.4 (4)C25—C26—H26119.7
O7—C7—C6112.0 (4)C26—C27—C28119.5 (7)
C8—C7—C6110.6 (3)C26—C27—H27120.2
O7—C7—H7108.9C28—C27—H27120.2
C8—C7—H7108.9C29—C28—C27120.7 (6)
C6—C7—H7108.9C29—C28—H28119.6
C7—C8—C15110.7 (3)C27—C28—H28119.6
C7—C8—C14109.6 (3)C28—C29—C24119.1 (5)
C15—C8—C14111.7 (4)C28—C29—C30123.3 (5)
C7—C8—C9110.5 (3)C24—C29—C30117.6 (6)
C15—C8—C9115.1 (4)O2B—C30—O2A122.2 (5)
C14—C8—C998.8 (3)O2B—C30—C29125.8 (5)
C8—C9—C11105.6 (3)O2A—C30—C29112.0 (5)
C8—C9—C10100.8 (3)C32—C31—H31A109.5
C11—C9—C10123.0 (3)C32—C31—H31B109.5
C8—C9—H9108.8H31A—C31—H31B109.5
C11—C9—H9108.8C32—C31—H31C109.5
C10—C9—H9108.8H31A—C31—H31C109.5
C1—C10—C9115.8 (3)H31B—C31—H31C109.5
C1—C10—C5113.2 (3)O3B—C32—O3A122.7 (6)
C9—C10—C5105.3 (3)O3B—C32—C31127.8 (7)
C1—C10—C20114.9 (4)O3A—C32—C31109.4 (7)
C9—C10—C20104.4 (3)C34—C33—H33A109.5
C5—C10—C20101.8 (3)C34—C33—H33B109.5
O11A—C11—C12111.4 (4)H33A—C33—H33B109.5
O11A—C11—C9115.0 (3)C34—C33—H33C109.5
C12—C11—C9110.7 (4)H33A—C33—H33C109.5
O11A—C11—H11106.4H33B—C33—H33C109.5
C12—C11—H11106.4O11B—C34—O11A122.8 (4)
C9—C11—H11106.4O11B—C34—C33124.4 (5)
C16—C12—C13109.3 (4)O11A—C34—C33112.8 (5)
C16—C12—C11105.6 (4)C40—C35—C36121.5 (6)
C13—C12—C11110.9 (3)C40—C35—H35119.3
C16—C12—H12110.3C36—C35—H35119.3
C13—C12—H12110.3C37—C36—C35119.0 (6)
C11—C12—H12110.3C37—C36—H36120.5
O13A—C13—C12106.7 (4)C35—C36—H36120.5
O13A—C13—C14111.9 (3)C36—C37—C38120.9 (6)
C12—C13—C14110.1 (4)C36—C37—H37119.6
O13A—C13—H13109.3C38—C37—H37119.6
C12—C13—H13109.3C39—C38—C37119.6 (7)
C14—C13—H13109.3C39—C38—H38120.2
C13—C14—C20115.1 (3)C37—C38—H38120.2
C13—C14—C8109.5 (3)C38—C39—C40121.5 (6)
C20—C14—C8100.1 (3)C38—C39—H39119.3
C13—C14—H14110.6C40—C39—H39119.3
C20—C14—H14110.6C35—C40—C39117.5 (5)
C8—C14—H14110.6C35—C40—C41119.9 (5)
C16—C15—C8110.4 (3)C39—C40—C41122.6 (5)
C16—C15—H15A109.6O13B—C41—O13A123.0 (4)
C8—C15—H15A109.6O13B—C41—C40125.5 (5)
C16—C15—H15B109.6O13A—C41—C40111.4 (4)
C8—C15—H15B109.6

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7A···O19i0.821.942.743 (5)167

Symmetry codes: (i) −x, y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2424).

References

  • Deng, Y. P., Chen, D. H. & Sun, W. L. (1992). Acta Chim. Sinica, 50, 822–826.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst.22, 384–387.
  • Gabe, E. J. & White, P. S. (1993). American Crystallographic Association meeting, Pittsburgh. Abstract PA 104.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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