Talatisamine, a C19-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

Lei, J.; Luo, Y.-J.; Bian, Q.-Q.; Wang, X.-Q.

doi:10.1107/S1600536811044242

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3145-o3146

https://doi.org/10.1107/S1600536811044242

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Talatisamine, a C₁₉-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

Jun Lei,^a Ya-Jun Luo,^a Qing-Quan Bian ^a and Xiong-Qing Wang ^a ^*

^aInstitute of Chemistry and Chemical Engineering, Mianyang Normal University, Mianyang 621000, People's Republic of China
^*Correspondence e-mail: wangxq193@126.com

(Received 28 September 2011; accepted 24 October 2011; online 2 November 2011)

The title compound [systematic name: (1S,4S,5R,7S,8S,9R,10R,11S,13S,14S,16S,17R)-N-methyl-8,14-dihydroxy-1,16-trimethoxy-4-(methoxymethylene)aconitane], C₂₄H₃₉NO₅, was isolated from the roots of Aconitum carmichaelii Debx., which is known as `Chuanwu' in Chinese traditional herbal medicine. The molecule has an aconitane carbon skeleton with four six-membered rings and two five-membered rings, including a six-membered N-containing heterocyclic ring. Both five-membered rings adopt envelope conformations. The four six-membered adopt chair conformations. Two intramolecular O—H⋯O hydrogen bonds occur.

Related literature

The title compound is an aconitine-type C₁₉-diterpenoid alkaloid. For reviews of diterpenoid alkaloids, see: Wang et al. (2009 , 2010 ). For the chemical structure of the title compound established from NMR and MS data, see: Pelletier et al. (1984 ). For the total synthesis of the title compound, see: Wiesner et al. (1974 ). For structures of related C₁₉-diterpenoid alkaloids, see: Gao et al. (2010 ); Tashkhodjaev & Sultankhodjaev (2009 ); He et al. (2008 ). For the absolute configuration of aconitine-type C₁₉-diterpenoid alkaloids, see: Pelletier & Djarmati (1976 ); Tsuda & Marion (1963 ); Zhapova et al. (1986 ).

Experimental

Crystal data

C₂₄H₃₉NO₅
M_r = 421.56
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.7124 (4) Å
b = 13.9401 (7) Å
c = 16.3729 (8) Å
V = 2216.77 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.40 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
6644 measured reflections
2572 independent reflections
2068 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.097
S = 1.04
2572 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	2.28	2.926 (3)	136
O3—H3⋯O4	0.82	1.95	2.666 (3)	146

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811044242/xu5344sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811044242/xu5344Isup2.hkl

checkCIF report

Comment top

As a famous Chinese traditional herbal, the roots of Aconitum carmichaeli Debx., known as "Chuanwu", has been therapeutically used to the treatment of rheumatic pain, rheumatoid arthritis and some other inflammations. Recently, two important reviews focus on the alkaloids from the genus Aconitum (Wang et al., 2009 and 2010). The title compound, N-methyl-8β,14β-dihydroxy-1α,16β-trimethoxy-4β-(methoxymethylene)aconitane, talatisamine, has been isolated previously from many genus of AconitumL., inculding A. carmichaeli Debx. (Pelletier et al., 1984), and its structure was established from the NMR and MS data (Wiesner et al., 1974). However, in our recent investigation, it was isolation from the root of Aconitum carmichaeli Debx. collected in the Jiangyou country, Sichuan Province of China in June, 2011. The crystal structure of talatisamine has not been reported. In view of this, the crystal structure determination of the title compound was carried out and the result is presented here.

The molecular structure of the title compound is shown in Fig. 1. The molecule has a high rigid structure consisting of six main rings (A–F). Six-membered rings A (C1/C2/C3/C4/C5/C11), B (C7/C8/C9/C10/C11/C17) and D(C8/C9/C14/C13/C16/C15) adopt chair conformations; six-membered heterocyclicring E (C4/C5/C11/C17/N1/C19) adopts the same chair conformation. The five-membered rings C (C9/C10/C12/C13/C14) and F (C5/C6/C7/C17/C11) display anenvelope conformation, in which, the C14 and C11 act as the "envelope atom" respectively. Two cis-fused ring junctions are observed between rings A/E and between B/C. Two trans-fused ring junctions involve rings A/B and also E/F. The crystal structure contains intermolecular O—H···O hydrogen bond between the hydroxyl group and carbonyl O atom. The absolute configuration of the title compound can not be confirmed by the present MoKa diffraction data. But it can be assumed to be the same as that reported for C₁₉-diterpenoidalkaloids from the nature (Gao et al., 2010; Tashkhodjaev & Sultankhodjaev, 2009; He et al.., 2008; Pelletier & Djarmati, 1976; Tsuda & Marion, 1963; Zhapova et al., 1986).

Related literature top

The title compound is an aconitine-type C₁₉-diterpenoid alkaloid. For reviews of diterpenoid alkaloids, see: Wang et al. (2009, 2010). For the chemical structure of the title compound established from NMR and MS data, see: Pelletier et al. (1984). For the total synthesis of the title compound, see: Wiesner et al. (1974). For structures of related C₁₉-diterpenoid alkaloids, see: Gao et al. (2010); Tashkhodjaev & Sultankhodjaev (2009); He et al. (2008). For the absolute configuration of aconitine-type C₁₉-diterpenoid alkaloids, see: Pelletier & Djarmati (1976); Tsuda & Marion (1963); Zhapova et al. (1986).

Experimental top

The title compound was isolated from the roots of Aconitum carmichaeli Debx. according to the literature procedure of Gao et al. (2010) and crystals of X-ray quality were grown from MeOH at room temperature by slow evaporation.

Structure description top

The title compound is an aconitine-type C₁₉-diterpenoid alkaloid. For reviews of diterpenoid alkaloids, see: Wang et al. (2009, 2010). For the chemical structure of the title compound established from NMR and MS data, see: Pelletier et al. (1984). For the total synthesis of the title compound, see: Wiesner et al. (1974). For structures of related C₁₉-diterpenoid alkaloids, see: Gao et al. (2010); Tashkhodjaev & Sultankhodjaev (2009); He et al. (2008). For the absolute configuration of aconitine-type C₁₉-diterpenoid alkaloids, see: Pelletier & Djarmati (1976); Tsuda & Marion (1963); Zhapova et al. (1986).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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

	Fig. 1. The molecular structure of the title compound with the atom numbering, showing displacement ellipsoids at the 30% probability level.
	Fig. 2. Molecular packing of the title compound.

(1S,4S,5R,7S,8S,9R,10R, 11S,13S,14S,16S,17R)-N-methyl- 8,14-dihydroxy-1,16-trimethoxy-4-(methoxymethylene)aconitane top

Crystal data top

C₂₄H₃₉NO₅	F(000) = 920
M_r = 421.56	D_x = 1.263 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2165 reflections
a = 9.7124 (4) Å	θ = 2.9–29.1°
b = 13.9401 (7) Å	µ = 0.09 mm⁻¹
c = 16.3729 (8) Å	T = 293 K
V = 2216.77 (17) Å³	Block, colourless
Z = 4	0.40 × 0.40 × 0.35 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 26.4°, θ_min = 2.9°
Detector resolution: 16.0874 pixels mm^-1	h = −11→12
ω scans	k = −17→16
6644 measured reflections	l = −16→20
2572 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0403P)² + 0.3082P] where P = (F_o² + 2F_c²)/3
2572 reflections	(Δ/σ)_max < 0.001
277 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₄H₃₉NO₅	V = 2216.77 (17) Å³
M_r = 421.56	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.7124 (4) Å	µ = 0.09 mm⁻¹
b = 13.9401 (7) Å	T = 293 K
c = 16.3729 (8) Å	0.40 × 0.40 × 0.35 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2068 reflections with I > 2σ(I)
6644 measured reflections	R_int = 0.026
2572 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.04	Δρ_max = 0.15 e Å⁻³
2572 reflections	Δρ_min = −0.15 e Å⁻³
277 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
O1	0.32334 (17)	0.44018 (14)	0.41854 (12)	0.0435 (5)
O2	0.89891 (18)	0.25592 (15)	0.37591 (14)	0.0564 (6)
H2	0.9046	0.2223	0.3350	0.085*
O3	0.7579 (2)	0.17270 (16)	0.23475 (15)	0.0605 (6)
H3	0.7429	0.1208	0.2565	0.091*
O4	0.6335 (2)	0.05223 (14)	0.33745 (13)	0.0561 (6)
O5	0.7984 (2)	0.70995 (17)	0.35432 (14)	0.0662 (6)
N1	0.6111 (2)	0.47017 (16)	0.54202 (13)	0.0365 (5)
C1	0.4310 (2)	0.50466 (19)	0.39450 (17)	0.0368 (6)
H1	0.4124	0.5232	0.3378	0.044*
C2	0.4232 (3)	0.5949 (2)	0.44516 (18)	0.0448 (7)
H2B	0.4167	0.5780	0.5025	0.054*
H2A	0.3411	0.6306	0.4305	0.054*
C3	0.5493 (3)	0.6571 (2)	0.43140 (19)	0.0440 (7)
H3B	0.5462	0.7114	0.4683	0.053*
H3A	0.5480	0.6816	0.3760	0.053*
C4	0.6830 (3)	0.60164 (19)	0.44529 (16)	0.0385 (6)
C5	0.6955 (2)	0.51749 (18)	0.38407 (17)	0.0356 (6)
H5	0.7034	0.5407	0.3278	0.043*
C6	0.8211 (3)	0.45461 (19)	0.40829 (18)	0.0402 (7)
H6A	0.8734	0.4363	0.3603	0.048*
H6B	0.8812	0.4891	0.4454	0.048*
C7	0.7596 (2)	0.3657 (2)	0.45023 (17)	0.0375 (6)
H7	0.8128	0.3489	0.4990	0.045*
C8	0.7561 (3)	0.2812 (2)	0.38994 (17)	0.0403 (7)
C9	0.6954 (3)	0.31884 (19)	0.30943 (16)	0.0381 (6)
H9	0.7625	0.3596	0.2812	0.046*
C10	0.5624 (2)	0.37418 (19)	0.32477 (16)	0.0356 (6)
H10	0.5415	0.4092	0.2744	0.043*
C11	0.5686 (2)	0.44982 (18)	0.39451 (15)	0.0317 (6)
C12	0.4537 (3)	0.29090 (19)	0.33160 (18)	0.0431 (7)
H12B	0.4238	0.2833	0.3878	0.052*
H12A	0.3739	0.3047	0.2980	0.052*
C13	0.5264 (3)	0.1990 (2)	0.30144 (17)	0.0434 (7)
H13	0.4657	0.1614	0.2659	0.052*
C14	0.6491 (3)	0.2379 (2)	0.25413 (17)	0.0459 (7)
H14	0.6152	0.2659	0.2031	0.055*
C15	0.6805 (3)	0.1936 (2)	0.42678 (18)	0.0459 (7)
H15B	0.7498	0.1481	0.4447	0.055*
H15A	0.6317	0.2152	0.4751	0.055*
C16	0.5773 (3)	0.13917 (19)	0.37274 (18)	0.0448 (7)
H16	0.4978	0.1216	0.4064	0.054*
C17	0.6132 (2)	0.40139 (19)	0.47427 (15)	0.0338 (6)
H17	0.5530	0.3468	0.4864	0.041*
C18	0.8026 (3)	0.6714 (2)	0.43440 (19)	0.0491 (8)
H18B	0.7958	0.7227	0.4742	0.059*
H18A	0.8892	0.6382	0.4430	0.059*
C19	0.6885 (3)	0.55955 (19)	0.53215 (17)	0.0425 (7)
H19A	0.7839	0.5479	0.5465	0.051*
H19B	0.6525	0.6067	0.5701	0.051*
C20	0.6367 (3)	0.4256 (2)	0.62167 (17)	0.0474 (7)
H20B	0.7342	0.4300	0.6341	0.057*
H20A	0.6127	0.3582	0.6187	0.057*
C21	0.5563 (4)	0.4716 (2)	0.68945 (19)	0.0646 (9)
H21A	0.4601	0.4712	0.6759	0.097*
H21C	0.5868	0.5366	0.6966	0.097*
H21B	0.5706	0.4365	0.7392	0.097*
C22	0.1962 (3)	0.4556 (2)	0.3787 (2)	0.0625 (9)
H22A	0.2084	0.4491	0.3208	0.094*
H22C	0.1634	0.5189	0.3909	0.094*
H22B	0.1303	0.4091	0.3973	0.094*
C23	0.9152 (4)	0.7649 (3)	0.3346 (2)	0.0748 (11)
H23A	0.9080	0.7870	0.2793	0.112*
H23B	0.9964	0.7262	0.3404	0.112*
H23C	0.9210	0.8190	0.3707	0.112*
C24	0.6424 (4)	−0.0258 (2)	0.3919 (2)	0.0741 (11)
H24B	0.6771	−0.0810	0.3635	0.111*
H24A	0.5527	−0.0399	0.4134	0.111*
H24C	0.7035	−0.0098	0.4359	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0259 (9)	0.0517 (11)	0.0530 (11)	−0.0006 (10)	−0.0017 (8)	0.0075 (10)
O2	0.0364 (11)	0.0614 (14)	0.0715 (15)	0.0142 (11)	−0.0029 (10)	−0.0154 (12)
O3	0.0587 (12)	0.0572 (13)	0.0657 (16)	−0.0016 (12)	0.0165 (11)	−0.0190 (12)
O4	0.0651 (13)	0.0430 (11)	0.0603 (13)	0.0047 (11)	0.0012 (11)	−0.0085 (11)
O5	0.0634 (13)	0.0682 (14)	0.0670 (15)	−0.0224 (13)	−0.0008 (12)	0.0161 (12)
N1	0.0382 (11)	0.0412 (12)	0.0300 (11)	−0.0002 (11)	−0.0029 (10)	−0.0015 (10)
C1	0.0279 (12)	0.0447 (15)	0.0378 (16)	0.0005 (13)	−0.0033 (12)	0.0065 (12)
C2	0.0360 (14)	0.0466 (16)	0.0518 (18)	0.0059 (14)	0.0000 (13)	0.0005 (15)
C3	0.0427 (15)	0.0407 (15)	0.0486 (17)	0.0047 (14)	−0.0016 (13)	−0.0011 (13)
C4	0.0369 (14)	0.0371 (14)	0.0414 (16)	−0.0017 (13)	−0.0041 (12)	−0.0010 (12)
C5	0.0274 (12)	0.0435 (14)	0.0360 (15)	−0.0021 (12)	−0.0004 (11)	0.0008 (13)
C6	0.0276 (12)	0.0482 (16)	0.0449 (16)	−0.0010 (14)	−0.0043 (12)	−0.0064 (14)
C7	0.0285 (12)	0.0430 (15)	0.0410 (16)	0.0022 (12)	−0.0093 (12)	−0.0026 (13)
C8	0.0314 (13)	0.0436 (15)	0.0459 (16)	0.0044 (13)	−0.0037 (12)	−0.0054 (14)
C9	0.0359 (13)	0.0430 (15)	0.0354 (14)	−0.0062 (14)	0.0001 (12)	−0.0016 (12)
C10	0.0316 (12)	0.0445 (14)	0.0305 (14)	−0.0012 (13)	−0.0052 (11)	−0.0007 (12)
C11	0.0255 (11)	0.0377 (14)	0.0318 (14)	0.0004 (12)	−0.0013 (10)	0.0015 (11)
C12	0.0352 (14)	0.0495 (16)	0.0447 (16)	−0.0038 (14)	−0.0087 (13)	−0.0032 (14)
C13	0.0394 (15)	0.0495 (17)	0.0413 (16)	−0.0062 (14)	−0.0032 (13)	−0.0107 (14)
C14	0.0458 (16)	0.0530 (17)	0.0389 (16)	−0.0011 (15)	0.0012 (13)	−0.0081 (14)
C15	0.0501 (17)	0.0405 (15)	0.0471 (17)	0.0035 (15)	−0.0062 (14)	−0.0014 (13)
C16	0.0444 (15)	0.0428 (15)	0.0473 (17)	−0.0024 (14)	0.0063 (14)	−0.0055 (14)
C17	0.0302 (12)	0.0371 (13)	0.0339 (14)	0.0001 (12)	−0.0058 (11)	−0.0021 (12)
C18	0.0472 (16)	0.0451 (16)	0.0550 (19)	−0.0078 (16)	−0.0027 (15)	−0.0015 (15)
C19	0.0428 (15)	0.0443 (15)	0.0406 (15)	−0.0008 (15)	−0.0051 (13)	−0.0056 (13)
C20	0.0462 (15)	0.0544 (17)	0.0416 (16)	0.0001 (15)	−0.0075 (14)	−0.0002 (15)
C21	0.088 (2)	0.068 (2)	0.0375 (17)	0.000 (2)	−0.0023 (17)	−0.0056 (16)
C22	0.0278 (13)	0.071 (2)	0.089 (3)	0.0022 (16)	−0.0100 (16)	0.008 (2)
C23	0.068 (2)	0.073 (2)	0.084 (3)	−0.021 (2)	0.017 (2)	0.006 (2)
C24	0.084 (3)	0.0498 (19)	0.088 (3)	0.009 (2)	−0.001 (2)	−0.003 (2)

Geometric parameters (Å, º) top

O1—C1	1.434 (3)	C9—C10	1.526 (4)
O1—C22	1.413 (3)	C9—C14	1.515 (4)
O2—H2	0.8200	C10—H10	0.9800
O2—C8	1.449 (3)	C10—C11	1.556 (3)
O3—H3	0.8200	C10—C12	1.573 (4)
O3—C14	1.429 (3)	C11—C17	1.532 (3)
O4—C16	1.449 (3)	C12—H12B	0.9700
O4—C24	1.410 (4)	C12—H12A	0.9700
O5—C18	1.418 (4)	C12—C13	1.543 (4)
O5—C23	1.406 (4)	C13—H13	0.9800
N1—C17	1.466 (3)	C13—C14	1.521 (4)
N1—C19	1.464 (3)	C13—C16	1.518 (4)
N1—C20	1.466 (3)	C14—H14	0.9800
C1—H1	0.9800	C15—H15B	0.9700
C1—C2	1.508 (4)	C15—H15A	0.9700
C1—C11	1.540 (3)	C15—C16	1.537 (4)
C2—H2B	0.9700	C16—H16	0.9800
C2—H2A	0.9700	C17—H17	0.9800
C2—C3	1.518 (4)	C18—H18B	0.9700
C3—H3B	0.9700	C18—H18A	0.9700
C3—H3A	0.9700	C19—H19A	0.9700
C3—C4	1.527 (4)	C19—H19B	0.9700
C4—C5	1.548 (4)	C20—H20B	0.9700
C4—C18	1.525 (4)	C20—H20A	0.9700
C4—C19	1.539 (4)	C20—C21	1.501 (4)
C5—H5	0.9800	C21—H21A	0.9600
C5—C6	1.554 (3)	C21—H21C	0.9600
C5—C11	1.561 (3)	C21—H21B	0.9600
C6—H6A	0.9700	C22—H22A	0.9600
C6—H6B	0.9700	C22—H22C	0.9600
C6—C7	1.538 (4)	C22—H22B	0.9600
C7—H7	0.9800	C23—H23A	0.9600
C7—C8	1.537 (4)	C23—H23B	0.9600
C7—C17	1.558 (3)	C23—H23C	0.9600
C8—C9	1.536 (4)	C24—H24B	0.9600
C8—C15	1.548 (4)	C24—H24A	0.9600
C9—H9	0.9800	C24—H24C	0.9600

O1—C1—H1	106.9	C8—C15—H15A	107.7
O1—C1—C2	109.6 (2)	C9—C8—C7	107.3 (2)
O1—C1—C11	108.77 (19)	C9—C8—C15	114.9 (2)
O1—C22—H22A	109.5	C9—C10—H10	106.8
O1—C22—H22C	109.5	C9—C10—C11	115.5 (2)
O1—C22—H22B	109.5	C9—C10—C12	101.9 (2)
O2—C8—C7	105.5 (2)	C9—C14—C13	101.2 (2)
O2—C8—C9	108.3 (2)	C9—C14—H14	108.2
O2—C8—C15	108.9 (2)	C10—C9—C8	110.9 (2)
O3—C14—C9	112.7 (2)	C10—C9—H9	110.3
O3—C14—C13	117.8 (2)	C10—C11—C5	111.1 (2)
O3—C14—H14	108.2	C10—C12—H12B	110.4
O4—C16—C13	106.0 (2)	C10—C12—H12A	110.4
O4—C16—C15	113.4 (2)	C11—C1—H1	106.9
O4—C16—H16	108.2	C11—C5—H5	111.4
O4—C24—H24B	109.5	C11—C10—H10	106.8
O4—C24—H24A	109.5	C11—C10—C12	118.3 (2)
O4—C24—H24C	109.5	C11—C17—C7	100.6 (2)
O5—C18—C4	109.1 (2)	C11—C17—H17	110.3
O5—C18—H18B	109.9	C12—C10—H10	106.8
O5—C18—H18A	109.9	C12—C13—H13	111.0
O5—C23—H23A	109.5	H12B—C12—H12A	108.6
O5—C23—H23B	109.5	C13—C12—C10	106.4 (2)
O5—C23—H23C	109.5	C13—C12—H12B	110.4
N1—C17—C7	114.36 (19)	C13—C12—H12A	110.4
N1—C17—C11	110.7 (2)	C13—C14—H14	108.2
N1—C17—H17	110.3	C13—C16—C15	112.6 (2)
N1—C19—C4	114.1 (2)	C13—C16—H16	108.2
N1—C19—H19A	108.7	C14—O3—H3	109.5
N1—C19—H19B	108.7	C14—C9—C8	111.9 (2)
N1—C20—H20B	109.0	C14—C9—H9	110.3
N1—C20—H20A	109.0	C14—C9—C10	102.9 (2)
N1—C20—C21	112.9 (2)	C14—C13—C12	103.1 (2)
C1—C2—H2B	109.5	C14—C13—H13	111.0
C1—C2—H2A	109.5	C15—C16—H16	108.2
C1—C2—C3	110.7 (2)	H15B—C15—H15A	107.1
C1—C11—C5	112.7 (2)	C16—C13—C12	111.0 (2)
C1—C11—C10	107.6 (2)	C16—C13—H13	111.0
C2—C1—H1	106.9	C16—C13—C14	109.4 (2)
C2—C1—C11	117.2 (2)	C16—C15—C8	118.3 (2)
C2—C3—H3B	109.2	C16—C15—H15B	107.7
C2—C3—H3A	109.2	C16—C15—H15A	107.7
C2—C3—C4	112.0 (2)	C17—C7—H7	110.6
H2B—C2—H2A	108.1	C17—C11—C1	117.6 (2)
C3—C2—H2B	109.5	C17—C11—C5	97.86 (19)
C3—C2—H2A	109.5	C17—C11—C10	109.7 (2)
C3—C4—C5	110.7 (2)	C18—C4—C3	107.9 (2)
C3—C4—C19	111.1 (2)	C18—C4—C5	110.3 (2)
H3B—C3—H3A	107.9	C18—C4—C19	108.9 (2)
C4—C3—H3B	109.2	H18B—C18—H18A	108.3
C4—C3—H3A	109.2	C19—N1—C17	117.8 (2)
C4—C5—H5	111.4	C19—N1—C20	111.8 (2)
C4—C5—C6	108.9 (2)	C19—C4—C5	107.9 (2)
C4—C5—C11	109.0 (2)	H19A—C19—H19B	107.6
C4—C18—H18B	109.9	C20—N1—C17	113.2 (2)
C4—C18—H18A	109.9	C20—C21—H21A	109.5
C4—C19—H19A	108.7	C20—C21—H21C	109.5
C4—C19—H19B	108.7	C20—C21—H21B	109.5
C5—C6—H6A	110.7	H20B—C20—H20A	107.8
C5—C6—H6B	110.7	C21—C20—H20B	109.0
C6—C5—H5	111.4	C21—C20—H20A	109.0
C6—C5—C11	104.53 (19)	H21A—C21—H21C	109.5
C6—C7—H7	110.6	H21A—C21—H21B	109.5
C6—C7—C17	102.1 (2)	H21C—C21—H21B	109.5
H6A—C6—H6B	108.8	C22—O1—C1	114.6 (2)
C7—C6—C5	105.31 (19)	H22A—C22—H22C	109.5
C7—C6—H6A	110.7	H22A—C22—H22B	109.5
C7—C6—H6B	110.7	H22C—C22—H22B	109.5
C7—C8—C15	111.4 (2)	C23—O5—C18	113.3 (3)
C7—C17—H17	110.3	H23A—C23—H23B	109.5
C8—O2—H2	109.5	H23A—C23—H23C	109.5
C8—C7—C6	109.8 (2)	H23B—C23—H23C	109.5
C8—C7—H7	110.6	C24—O4—C16	114.6 (2)
C8—C7—C17	112.8 (2)	H24B—C24—H24A	109.5
C8—C9—H9	110.3	H24B—C24—H24C	109.5
C8—C15—H15B	107.7	H24A—C24—H24C	109.5

O1—C1—C2—C3	170.4 (2)	C9—C10—C11—C1	174.2 (2)
O1—C1—C11—C5	−170.0 (2)	C9—C10—C11—C5	50.5 (3)
O1—C1—C11—C10	67.2 (2)	C9—C10—C11—C17	−56.6 (3)
O1—C1—C11—C17	−57.3 (3)	C9—C10—C12—C13	−12.0 (3)
O2—C8—C9—C10	−162.8 (2)	C10—C9—C14—O3	−177.0 (2)
O2—C8—C9—C14	82.9 (3)	C10—C9—C14—C13	−50.3 (3)
O2—C8—C15—C16	−108.1 (3)	C10—C11—C17—N1	−176.36 (19)
C1—C2—C3—C4	−53.5 (3)	C10—C11—C17—C7	62.4 (2)
C1—C11—C17—N1	−52.9 (3)	C10—C12—C13—C14	−18.0 (3)
C1—C11—C17—C7	−174.2 (2)	C10—C12—C13—C16	99.0 (2)
C2—C1—C11—C5	−45.0 (3)	C11—C1—C2—C3	45.9 (3)
C2—C1—C11—C10	−167.8 (2)	C11—C5—C6—C7	−13.3 (3)
C2—C1—C11—C17	67.7 (3)	C11—C10—C12—C13	−139.9 (2)
C2—C3—C4—C5	62.1 (3)	C12—C10—C11—C1	−64.6 (3)
C2—C3—C4—C18	−177.1 (2)	C12—C10—C11—C5	171.6 (2)
C2—C3—C4—C19	−57.7 (3)	C12—C10—C11—C17	64.5 (3)
C3—C4—C5—C6	−171.8 (2)	C12—C13—C14—O3	164.7 (2)
C3—C4—C5—C11	−58.4 (3)	C12—C13—C14—C9	41.4 (3)
C3—C4—C18—O5	−59.6 (3)	C12—C13—C16—O4	175.7 (2)
C3—C4—C19—N1	80.8 (3)	C12—C13—C16—C15	−59.8 (3)
C4—C5—C6—C7	103.0 (2)	C14—C9—C10—C11	167.5 (2)
C4—C5—C11—C1	49.3 (3)	C14—C9—C10—C12	37.9 (3)
C4—C5—C11—C10	170.1 (2)	C14—C13—C16—O4	−71.2 (3)
C4—C5—C11—C17	−75.1 (2)	C14—C13—C16—C15	53.3 (3)
C5—C4—C18—O5	61.5 (3)	C15—C8—C9—C10	75.1 (3)
C5—C4—C19—N1	−40.7 (3)	C15—C8—C9—C14	−39.1 (3)
C5—C6—C7—C8	100.3 (2)	C16—C13—C14—O3	46.5 (3)
C5—C6—C7—C17	−19.6 (3)	C16—C13—C14—C9	−76.8 (3)
C5—C11—C17—N1	67.8 (2)	C17—N1—C19—C4	37.6 (3)
C5—C11—C17—C7	−53.4 (2)	C17—N1—C20—C21	−144.9 (2)
C6—C5—C11—C1	165.6 (2)	C17—C7—C8—O2	−178.7 (2)
C6—C5—C11—C10	−73.6 (2)	C17—C7—C8—C9	66.0 (3)
C6—C5—C11—C17	41.1 (2)	C17—C7—C8—C15	−60.6 (3)
C6—C7—C8—O2	68.2 (3)	C18—C4—C5—C6	68.8 (3)
C6—C7—C8—C9	−47.2 (3)	C18—C4—C5—C11	−177.8 (2)
C6—C7—C8—C15	−173.8 (2)	C18—C4—C19—N1	−160.5 (2)
C6—C7—C17—N1	−72.3 (3)	C19—N1—C17—C7	58.9 (3)
C6—C7—C17—C11	46.3 (2)	C19—N1—C17—C11	−53.8 (3)
C7—C8—C9—C10	−49.4 (3)	C19—N1—C20—C21	79.3 (3)
C7—C8—C9—C14	−163.6 (2)	C19—C4—C5—C6	−50.1 (3)
C7—C8—C15—C16	135.9 (2)	C19—C4—C5—C11	63.4 (3)
C8—C7—C17—N1	169.9 (2)	C19—C4—C18—O5	179.7 (2)
C8—C7—C17—C11	−71.5 (3)	C20—N1—C17—C7	−74.2 (3)
C8—C9—C10—C11	47.8 (3)	C20—N1—C17—C11	173.1 (2)
C8—C9—C10—C12	−81.9 (2)	C20—N1—C19—C4	171.3 (2)
C8—C9—C14—O3	−58.0 (3)	C22—O1—C1—C2	86.3 (3)
C8—C9—C14—C13	68.8 (3)	C22—O1—C1—C11	−144.4 (2)
C8—C15—C16—O4	99.8 (3)	C23—O5—C18—C4	−171.7 (2)
C8—C15—C16—C13	−20.5 (3)	C24—O4—C16—C13	−159.0 (3)
C9—C8—C15—C16	13.6 (3)	C24—O4—C16—C15	77.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	2.28	2.926 (3)	136
O3—H3···O4	0.82	1.95	2.666 (3)	146

Experimental details

Crystal data
Chemical formula	C₂₄H₃₉NO₅
M_r	421.56
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.7124 (4), 13.9401 (7), 16.3729 (8)
V (Å³)	2216.77 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.40 × 0.35

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6644, 2572, 2068
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.097, 1.04
No. of reflections	2572
No. of parameters	277
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	2.28	2.926 (3)	136.0
O3—H3···O4	0.82	1.95	2.666 (3)	145.6

Acknowledgements

This project was supported by the Scientific Research Fund of Mianyang Normal University, China.

References

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