(1β,2α,3α,7α,11α,13β)-1,3,7,11-Tetra­acet­oxy-2,13-bis­(benz­yloxy)-21-methyl-19,21-secohetisan-19-al hemi­hydrate

Chen, F.-Z.; Xiang, Q.-X.; Zhang, Y.-Q.; Xiong, J.-R.

doi:10.1107/S1600536809018315

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1432

doi:10.1107/S1600536809018315

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(1β,2α,3α,7α,11α,13β)-1,3,7,11-Tetraacetoxy-2,13-bis(benzyloxy)-21-methyl-19,21-secohetisan-19-al hemihydrate

Feng-Zheng Chen,^a ^* Qing-Xiang Xiang,^a Yuan-Qin Zhang ^a and Jun-Ru Xiong ^a

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

(Received 7 April 2009; accepted 14 May 2009; online 29 May 2009)

In the crystal structure of the title compound, C₄₃H₄₆NO₁₃·0.5H₂O, the molecule assumes a U-shaped conformation, the terminal benzene rings being approximately parallel and partially overlapped with each other. The molecule contains eight alicyclic and heterocyclic rings. The cyclohexane rings adopt chair conformations, the other three six-membered carbocyclic rings form a bicyclo[2.2.2]octane system with a boat conformation for each six-membered ring, the six-membered heterocyclic ring has a chair conformation and both of the five-membered rings have envelope conformations. The solvent water molecule links with the organic molecule via classic O—H⋯O and weak C—H⋯O hydrogen bonding in the crystal structure.

Related literature

For general background, see: Deng et al. (1992 ).

Experimental

Crystal data

C₄₃H₄₆NO₁₃·0.5H₂O
M_r = 793.82
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.517 (3) Å
b = 18.045 (4) Å
c = 19.241 (4) Å
V = 3998.7 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 292 K
0.52 × 0.46 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
4333 measured reflections
4092 independent reflections
2220 reflections with I > 2σ(I)
R_int = 0.007
3 standard reflections every 250 reflections intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.150
S = 1.00
4092 reflections
530 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O11ⁱ	0.89	2.38	3.205 (15)	155
O1W—H1B⋯O6	0.90	2.39	3.208 (15)	151
C15—H15A⋯O4ⁱⁱ	0.97	2.48	3.359 (8)	150
C23—H23B⋯O1W	0.96	2.58	3.491 (17)	159
C29—H29⋯O7ⁱⁱⁱ	0.93	2.40	3.290 (8)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018315/xu2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018315/xu2510Isup2.hkl

checkCIF report

Comment top

The diterpenoid alkaloid, acetyldelgradine, has been isolated from Delphiniumgrandiflorum L. (Deng et al., 1992) and its structure was established from the spectroscopic data. In our current investigation, the title compound was isolated from Aconitum carmichaeli Debx, and its structure was confirmed by X-ray diffraction study.

Themolecular 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 lattice water molecule links with the organic molecule via O—H···O hydrogen bonding, and weak molecular C—H···O hydrogen bonding is also present in the crystal structure (Table 1).

Related literature top

For general background, see: Deng et al. (1992).

Experimental top

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-water solution at room temperature.

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Dashed line indicates hydrogen bonding.

(1β,2α,3α,7α,11α,13β)-1,3,7,11-Tetraacetoxy-2,13-bis(benzyloxy)- 21-dimethyl-19,21-secohetisan-19-al hemihydrate top

Crystal data top

C₄₃H₄₆NO₁₃·0.5H₂O	F(000) = 1680
M_r = 793.82	D_x = 1.319 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 36 reflections
a = 11.517 (3) Å	θ = 4.6–9.6°
b = 18.045 (4) Å	µ = 0.10 mm⁻¹
c = 19.241 (4) Å	T = 292 K
V = 3998.7 (16) Å³	Block, colourless
Z = 4	0.52 × 0.46 × 0.42 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.007
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.6°
Graphite monochromator	h = −3→13
ω/2θ scans	k = −8→21
4333 measured reflections	l = −4→23
4092 independent reflections	3 standard reflections every 250 reflections
2220 reflections with I > 2σ(I)	intensity decay: 2.0%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0817P)²] where P = (F_o² + 2F_c²)/3
4092 reflections	(Δ/σ)_max = 0.001
530 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₄₃H₄₆NO₁₃·0.5H₂O	V = 3998.7 (16) Å³
M_r = 793.82	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.517 (3) Å	µ = 0.10 mm⁻¹
b = 18.045 (4) Å	T = 292 K
c = 19.241 (4) Å	0.52 × 0.46 × 0.42 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.007
4333 measured reflections	3 standard reflections every 250 reflections
4092 independent reflections	intensity decay: 2.0%
2220 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
4092 reflections	Δρ_min = −0.24 e Å⁻³
530 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
N1	0.8109 (4)	0.4658 (2)	0.2072 (2)	0.0424 (10)
O1	0.4566 (3)	0.41227 (19)	0.30263 (17)	0.0473 (9)
O2	0.3551 (4)	0.3061 (3)	0.3012 (3)	0.0824 (13)
O3	0.6957 (3)	0.29181 (18)	0.25073 (15)	0.0438 (8)
O4	0.6532 (5)	0.1788 (2)	0.2904 (3)	0.109 (2)
O5	0.7455 (3)	0.3093 (2)	0.39340 (16)	0.0563 (10)
O6	0.6180 (7)	0.2970 (4)	0.4783 (3)	0.137 (3)
O7	0.9560 (4)	0.4295 (2)	0.3264 (2)	0.0677 (12)
O8	0.7968 (4)	0.63060 (19)	0.16840 (17)	0.0547 (10)
O9	0.8387 (5)	0.6961 (2)	0.2649 (2)	0.0863 (16)
O10	0.3615 (3)	0.4339 (2)	0.16916 (18)	0.0506 (9)
O11	0.2044 (4)	0.4848 (3)	0.1230 (3)	0.0971 (16)
O12	0.5520 (3)	0.38202 (18)	0.07900 (15)	0.0492 (10)
O13	0.7089 (5)	0.3518 (2)	0.0167 (2)	0.0816 (14)
O1W	0.4527 (15)	0.4368 (6)	0.5068 (7)	0.157 (5)	0.50
H1A	0.3997	0.4441	0.5398	0.236*	0.50
H1B	0.5077	0.4021	0.5148	0.236*	0.50
C1	0.5433 (4)	0.3818 (3)	0.2552 (2)	0.0405 (12)
H1	0.5055	0.3574	0.2157	0.049*
C2	0.6125 (5)	0.3258 (3)	0.2978 (2)	0.0438 (13)
H2	0.5599	0.2876	0.3158	0.053*
C3	0.6726 (5)	0.3642 (3)	0.3580 (2)	0.0490 (15)
H3	0.6127	0.3804	0.3908	0.059*
C4	0.7491 (5)	0.4309 (3)	0.3412 (2)	0.0468 (14)
C5	0.6813 (5)	0.4848 (3)	0.2924 (2)	0.0418 (13)
H5	0.6320	0.5182	0.3197	0.050*
C6	0.7700 (5)	0.5288 (3)	0.2504 (2)	0.0494 (14)
H6	0.8321	0.5487	0.2799	0.059*
C7	0.7118 (5)	0.5894 (3)	0.2074 (2)	0.0459 (13)
H7	0.6728	0.6236	0.2393	0.055*
C8	0.6210 (5)	0.5581 (3)	0.1574 (2)	0.0406 (12)
C9	0.5323 (4)	0.5144 (3)	0.2020 (2)	0.0397 (12)
H9	0.5078	0.5457	0.2409	0.048*
C10	0.6107 (4)	0.4495 (2)	0.2311 (2)	0.0362 (12)
C11	0.4261 (5)	0.5014 (3)	0.1534 (2)	0.0458 (13)
H11	0.3729	0.5432	0.1599	0.055*
C12	0.4632 (5)	0.5014 (3)	0.0769 (2)	0.0465 (14)
H12	0.4015	0.4816	0.0471	0.056*
C13	0.5756 (5)	0.4594 (3)	0.0665 (2)	0.0478 (14)
H13	0.6009	0.4655	0.0182	0.057*
C14	0.6697 (5)	0.4909 (3)	0.1149 (2)	0.0416 (13)
H14	0.7379	0.5061	0.0880	0.050*
C15	0.5672 (5)	0.6171 (3)	0.1110 (3)	0.0489 (14)
H15A	0.5222	0.6513	0.1391	0.059*
H15B	0.6280	0.6449	0.0879	0.059*
C16	0.4908 (5)	0.5817 (3)	0.0584 (2)	0.0507 (15)
C17	0.4573 (6)	0.6101 (3)	−0.0017 (3)	0.0678 (17)
H17A	0.4830	0.6577	−0.0136	0.102*
H17B	0.4097	0.5839	−0.0307	0.102*
C18	0.7737 (6)	0.4725 (3)	0.4089 (2)	0.0660 (18)
H18A	0.7038	0.4753	0.4360	0.099*
H18B	0.8004	0.5216	0.3984	0.099*
H18C	0.8323	0.4466	0.4348	0.099*
C19	0.8629 (5)	0.4042 (3)	0.3101 (3)	0.0517 (15)
H19	0.8607	0.3667	0.2771	0.062*
C20	0.7053 (4)	0.4388 (3)	0.1735 (2)	0.0394 (12)
H20	0.7120	0.3872	0.1581	0.047*
C21	0.9154 (5)	0.4730 (4)	0.1657 (3)	0.0621 (16)
H21A	0.9810	0.4798	0.1958	0.093*
H21B	0.9081	0.5150	0.1354	0.093*
H21C	0.9261	0.4290	0.1385	0.093*
C22	0.3641 (6)	0.3712 (4)	0.3187 (3)	0.0628 (17)
C23	0.2783 (6)	0.4138 (4)	0.3600 (4)	0.089 (2)
H23A	0.2664	0.4614	0.3390	0.133*
H23B	0.3069	0.4202	0.4065	0.133*
H23C	0.2061	0.3872	0.3613	0.133*
C24	0.7091 (5)	0.2182 (3)	0.2527 (3)	0.0515 (14)
C25	0.8001 (5)	0.1921 (3)	0.2039 (3)	0.0517 (14)
C26	0.8602 (6)	0.2382 (3)	0.1606 (3)	0.0606 (16)
H26	0.8440	0.2887	0.1613	0.073*
C27	0.9435 (6)	0.2121 (4)	0.1162 (3)	0.0739 (19)
H27	0.9840	0.2442	0.0871	0.089*
C28	0.9662 (7)	0.1361 (4)	0.1156 (4)	0.081 (2)
H28	1.0205	0.1172	0.0845	0.097*
C29	0.9110 (7)	0.0901 (4)	0.1591 (4)	0.082 (2)
H29	0.9305	0.0401	0.1597	0.098*
C30	0.8267 (6)	0.1156 (3)	0.2026 (4)	0.076 (2)
H30	0.7867	0.0829	0.2313	0.091*
C31	0.7080 (7)	0.2792 (4)	0.4532 (4)	0.0745 (19)
C32	0.7891 (7)	0.2250 (4)	0.4806 (3)	0.092 (2)
H32A	0.8670	0.2431	0.4752	0.138*
H32B	0.7807	0.1792	0.4558	0.138*
H32C	0.7733	0.2169	0.5290	0.138*
C33	0.8555 (6)	0.6848 (3)	0.2056 (4)	0.0667 (18)
C34	0.9414 (7)	0.7233 (4)	0.1601 (4)	0.099 (2)
H34A	0.9086	0.7302	0.1147	0.148*
H34B	1.0104	0.6937	0.1566	0.148*
H34C	0.9604	0.7706	0.1798	0.148*
C35	0.2509 (5)	0.4329 (3)	0.1512 (3)	0.0550 (15)
C36	0.1945 (6)	0.3630 (4)	0.1650 (4)	0.086 (2)
H36A	0.2522	0.3250	0.1705	0.130*
H36B	0.1445	0.3506	0.1268	0.130*
H36C	0.1494	0.3668	0.2067	0.130*
C37	0.6245 (6)	0.3329 (3)	0.0482 (3)	0.0553 (15)
C38	0.5864 (6)	0.2548 (3)	0.0582 (3)	0.0549 (16)
C39	0.6559 (7)	0.2000 (3)	0.0315 (3)	0.076 (2)
H39	0.7251	0.2121	0.0093	0.091*
C40	0.6216 (10)	0.1249 (4)	0.0379 (4)	0.100 (3)
H40	0.6682	0.0872	0.0204	0.120*
C41	0.5203 (10)	0.1088 (5)	0.0698 (5)	0.115 (3)
H41	0.4982	0.0594	0.0738	0.138*
C42	0.4482 (8)	0.1630 (4)	0.0966 (4)	0.100 (2)
H42	0.3782	0.1507	0.1178	0.120*
C43	0.4837 (6)	0.2370 (3)	0.0908 (3)	0.0716 (19)
H43	0.4374	0.2744	0.1092	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.033 (2)	0.046 (2)	0.048 (2)	0.001 (2)	−0.006 (2)	0.001 (2)
O1	0.044 (2)	0.052 (2)	0.0460 (19)	0.003 (2)	0.0148 (19)	0.0070 (17)
O2	0.063 (3)	0.079 (3)	0.105 (3)	−0.011 (3)	0.009 (3)	0.012 (3)
O3	0.048 (2)	0.0353 (19)	0.0476 (18)	0.0034 (19)	0.0071 (18)	0.0019 (15)
O4	0.129 (5)	0.049 (3)	0.149 (4)	0.007 (3)	0.079 (4)	0.026 (3)
O5	0.062 (3)	0.061 (2)	0.0456 (19)	0.000 (2)	−0.010 (2)	0.0157 (18)
O6	0.158 (6)	0.148 (6)	0.105 (4)	0.059 (5)	0.057 (4)	0.077 (4)
O7	0.058 (3)	0.064 (3)	0.081 (3)	−0.003 (2)	−0.023 (2)	0.018 (2)
O8	0.061 (2)	0.049 (2)	0.054 (2)	−0.010 (2)	−0.007 (2)	0.0110 (18)
O9	0.125 (4)	0.062 (3)	0.072 (3)	−0.010 (3)	−0.032 (3)	−0.006 (2)
O10	0.039 (2)	0.054 (2)	0.059 (2)	−0.004 (2)	0.000 (2)	0.0128 (19)
O11	0.055 (3)	0.092 (4)	0.144 (4)	0.002 (3)	−0.022 (3)	0.028 (4)
O12	0.062 (3)	0.044 (2)	0.0419 (18)	0.002 (2)	−0.001 (2)	−0.0032 (16)
O13	0.086 (3)	0.071 (3)	0.088 (3)	0.003 (3)	0.034 (3)	−0.003 (2)
O1W	0.212 (15)	0.086 (8)	0.174 (12)	0.009 (10)	−0.013 (13)	−0.010 (8)
C1	0.041 (3)	0.045 (3)	0.036 (2)	0.005 (3)	0.007 (3)	0.001 (2)
C2	0.051 (3)	0.042 (3)	0.039 (2)	0.006 (3)	0.005 (3)	0.003 (2)
C3	0.062 (4)	0.052 (3)	0.034 (2)	0.003 (3)	−0.001 (3)	0.006 (2)
C4	0.061 (4)	0.039 (3)	0.041 (3)	−0.003 (3)	−0.014 (3)	0.003 (2)
C5	0.054 (3)	0.036 (3)	0.036 (2)	−0.002 (3)	0.001 (3)	−0.005 (2)
C6	0.053 (4)	0.054 (3)	0.041 (3)	−0.005 (3)	−0.008 (3)	0.004 (3)
C7	0.061 (4)	0.038 (3)	0.039 (2)	−0.001 (3)	0.000 (3)	0.004 (2)
C8	0.049 (3)	0.039 (3)	0.034 (2)	0.006 (3)	0.000 (3)	0.004 (2)
C9	0.038 (3)	0.045 (3)	0.037 (2)	0.012 (3)	0.001 (2)	0.000 (2)
C10	0.031 (3)	0.038 (3)	0.040 (2)	0.000 (2)	−0.003 (2)	0.001 (2)
C11	0.041 (3)	0.046 (3)	0.050 (3)	0.006 (3)	0.003 (3)	0.007 (2)
C12	0.047 (3)	0.053 (3)	0.040 (3)	−0.002 (3)	0.000 (3)	0.008 (2)
C13	0.052 (4)	0.051 (3)	0.041 (3)	0.000 (3)	0.003 (3)	0.006 (2)
C14	0.047 (3)	0.042 (3)	0.036 (2)	0.000 (3)	0.006 (2)	0.007 (2)
C15	0.051 (4)	0.046 (3)	0.050 (3)	0.006 (3)	0.008 (3)	0.012 (2)
C16	0.055 (4)	0.056 (3)	0.041 (3)	0.015 (3)	−0.001 (3)	0.006 (3)
C17	0.069 (4)	0.068 (4)	0.066 (4)	0.017 (4)	0.000 (4)	0.012 (3)
C18	0.091 (5)	0.063 (4)	0.044 (3)	−0.006 (4)	−0.023 (3)	−0.002 (3)
C19	0.049 (4)	0.054 (3)	0.052 (3)	0.001 (3)	−0.016 (3)	0.011 (3)
C20	0.036 (3)	0.041 (3)	0.041 (2)	0.007 (3)	0.003 (3)	−0.002 (2)
C21	0.032 (3)	0.085 (4)	0.069 (4)	0.004 (3)	0.003 (3)	0.003 (3)
C22	0.051 (4)	0.086 (5)	0.052 (3)	0.013 (4)	0.012 (3)	0.020 (3)
C23	0.072 (5)	0.096 (5)	0.099 (5)	0.018 (4)	0.035 (4)	0.026 (4)
C24	0.054 (4)	0.041 (3)	0.060 (3)	0.003 (3)	0.008 (3)	0.007 (3)
C25	0.052 (3)	0.047 (3)	0.056 (3)	0.005 (3)	0.001 (3)	−0.001 (3)
C26	0.067 (4)	0.054 (3)	0.061 (3)	0.007 (3)	0.011 (4)	0.003 (3)
C27	0.073 (5)	0.082 (5)	0.067 (4)	0.007 (4)	0.021 (4)	0.000 (4)
C28	0.081 (5)	0.085 (5)	0.076 (4)	0.023 (5)	0.016 (4)	−0.017 (4)
C29	0.082 (5)	0.057 (4)	0.107 (5)	0.023 (4)	0.005 (5)	−0.019 (4)
C30	0.085 (5)	0.047 (4)	0.096 (4)	0.003 (4)	0.016 (5)	−0.005 (3)
C31	0.086 (5)	0.065 (4)	0.073 (4)	−0.005 (5)	0.007 (4)	0.025 (4)
C32	0.102 (6)	0.079 (5)	0.095 (5)	0.002 (5)	−0.018 (5)	0.050 (4)
C33	0.071 (5)	0.052 (4)	0.077 (4)	−0.018 (4)	−0.030 (4)	0.015 (4)
C34	0.100 (6)	0.087 (5)	0.110 (5)	−0.033 (5)	−0.021 (5)	0.024 (4)
C35	0.039 (4)	0.055 (4)	0.072 (4)	0.000 (3)	−0.002 (3)	0.007 (3)
C36	0.060 (4)	0.104 (5)	0.096 (5)	−0.017 (4)	−0.010 (4)	0.024 (4)
C37	0.063 (4)	0.055 (4)	0.048 (3)	0.009 (4)	−0.001 (3)	−0.008 (3)
C38	0.073 (5)	0.047 (3)	0.045 (3)	−0.002 (4)	−0.005 (3)	−0.012 (3)
C39	0.097 (6)	0.066 (4)	0.065 (4)	−0.002 (5)	0.004 (4)	−0.008 (3)
C40	0.136 (8)	0.060 (5)	0.105 (6)	0.011 (6)	0.009 (6)	−0.017 (4)
C41	0.148 (10)	0.061 (5)	0.135 (8)	−0.020 (6)	0.022 (7)	−0.017 (5)
C42	0.103 (6)	0.071 (5)	0.124 (6)	−0.016 (5)	0.016 (6)	0.007 (5)
C43	0.077 (5)	0.054 (4)	0.085 (4)	−0.003 (4)	0.008 (4)	−0.006 (3)

Geometric parameters (Å, º) top

N1—C21	1.450 (7)	C14—H14	0.9800
N1—C20	1.461 (6)	C15—C16	1.487 (7)
N1—C6	1.486 (6)	C15—H15A	0.9700
O1—C22	1.334 (7)	C15—H15B	0.9700
O1—C1	1.460 (5)	C16—C17	1.322 (7)
O2—C22	1.227 (8)	C17—H17A	0.9300
O3—C24	1.338 (6)	C17—H17B	0.9300
O3—C2	1.454 (6)	C18—H18A	0.9600
O4—C24	1.203 (6)	C18—H18B	0.9600
O5—C31	1.344 (7)	C18—H18C	0.9600
O5—C3	1.464 (6)	C19—H19	0.9300
O6—C31	1.188 (8)	C20—H20	0.9800
O7—C19	1.207 (6)	C21—H21A	0.9600
O8—C33	1.388 (7)	C21—H21B	0.9600
O8—C7	1.440 (6)	C21—H21C	0.9600
O9—C33	1.174 (8)	C22—C23	1.482 (9)
O10—C35	1.320 (7)	C23—H23A	0.9600
O10—C11	1.459 (6)	C23—H23B	0.9600
O11—C35	1.207 (7)	C23—H23C	0.9600
O12—C37	1.355 (7)	C24—C25	1.484 (7)
O12—C13	1.442 (6)	C25—C26	1.366 (7)
O13—C37	1.196 (7)	C25—C30	1.413 (7)
O1W—H1A	0.8898	C26—C27	1.369 (8)
O1W—H1B	0.9036	C26—H26	0.9300
C1—C10	1.521 (6)	C27—C28	1.396 (9)
C1—C2	1.526 (6)	C27—H27	0.9300
C1—H1	0.9800	C28—C29	1.341 (9)
C2—C3	1.518 (7)	C28—H28	0.9300
C2—H2	0.9800	C29—C30	1.362 (9)
C3—C4	1.528 (7)	C29—H29	0.9300
C3—H3	0.9800	C30—H30	0.9300
C4—C19	1.518 (8)	C31—C32	1.452 (9)
C4—C18	1.530 (7)	C32—H32A	0.9600
C4—C5	1.560 (7)	C32—H32B	0.9600
C5—C6	1.526 (7)	C32—H32C	0.9600
C5—C10	1.568 (6)	C33—C34	1.492 (10)
C5—H5	0.9800	C34—H34A	0.9600
C6—C7	1.526 (7)	C34—H34B	0.9600
C6—H6	0.9800	C34—H34C	0.9600
C7—C8	1.529 (7)	C35—C36	1.444 (8)
C7—H7	0.9800	C36—H36A	0.9600
C8—C15	1.522 (6)	C36—H36B	0.9600
C8—C9	1.549 (7)	C36—H36C	0.9600
C8—C14	1.565 (7)	C37—C38	1.487 (8)
C9—C11	1.558 (7)	C38—C39	1.372 (8)
C9—C10	1.581 (6)	C38—C43	1.377 (8)
C9—H9	0.9800	C39—C40	1.418 (9)
C10—C20	1.567 (6)	C39—H39	0.9300
C11—C12	1.533 (7)	C40—C41	1.349 (12)
C11—H11	0.9800	C40—H40	0.9300
C12—C13	1.513 (8)	C41—C42	1.383 (11)
C12—C16	1.525 (7)	C41—H41	0.9300
C12—H12	0.9800	C42—C43	1.400 (9)
C13—C14	1.539 (7)	C42—H42	0.9300
C13—H13	0.9800	C43—H43	0.9300
C14—C20	1.524 (6)

C21—N1—C20	118.4 (4)	C16—C17—H17A	120.0
C21—N1—C6	120.1 (4)	C16—C17—H17B	120.0
C20—N1—C6	103.9 (4)	H17A—C17—H17B	120.0
C22—O1—C1	118.8 (4)	C4—C18—H18A	109.5
C24—O3—C2	118.4 (4)	C4—C18—H18B	109.5
C31—O5—C3	119.2 (5)	H18A—C18—H18B	109.5
C33—O8—C7	115.2 (4)	C4—C18—H18C	109.5
C35—O10—C11	116.6 (4)	H18A—C18—H18C	109.5
C37—O12—C13	116.4 (4)	H18B—C18—H18C	109.5
H1A—O1W—H1B	117.6	O7—C19—C4	123.0 (5)
O1—C1—C10	103.7 (4)	O7—C19—H19	118.5
O1—C1—C2	105.7 (3)	C4—C19—H19	118.5
C10—C1—C2	115.4 (4)	N1—C20—C14	110.3 (4)
O1—C1—H1	110.5	N1—C20—C10	102.9 (4)
C10—C1—H1	110.5	C14—C20—C10	105.0 (4)
C2—C1—H1	110.5	N1—C20—H20	112.7
O3—C2—C3	111.5 (4)	C14—C20—H20	112.7
O3—C2—C1	106.8 (3)	C10—C20—H20	112.7
C3—C2—C1	110.3 (4)	N1—C21—H21A	109.5
O3—C2—H2	109.4	N1—C21—H21B	109.5
C3—C2—H2	109.4	H21A—C21—H21B	109.5
C1—C2—H2	109.4	N1—C21—H21C	109.5
O5—C3—C2	107.9 (4)	H21A—C21—H21C	109.5
O5—C3—C4	107.5 (4)	H21B—C21—H21C	109.5
C2—C3—C4	117.5 (4)	O2—C22—O1	122.4 (6)
O5—C3—H3	107.9	O2—C22—C23	126.0 (7)
C2—C3—H3	107.9	O1—C22—C23	111.7 (6)
C4—C3—H3	107.9	C22—C23—H23A	109.5
C19—C4—C3	109.3 (5)	C22—C23—H23B	109.5
C19—C4—C18	109.3 (5)	H23A—C23—H23B	109.5
C3—C4—C18	108.2 (4)	C22—C23—H23C	109.5
C19—C4—C5	113.2 (4)	H23A—C23—H23C	109.5
C3—C4—C5	109.3 (4)	H23B—C23—H23C	109.5
C18—C4—C5	107.4 (4)	O4—C24—O3	122.9 (5)
C6—C5—C4	107.9 (4)	O4—C24—C25	124.9 (5)
C6—C5—C10	99.2 (3)	O3—C24—C25	112.3 (5)
C4—C5—C10	117.3 (4)	C26—C25—C30	118.4 (6)
C6—C5—H5	110.6	C26—C25—C24	123.3 (5)
C4—C5—H5	110.6	C30—C25—C24	118.3 (5)
C10—C5—H5	110.6	C25—C26—C27	121.7 (6)
N1—C6—C5	96.3 (4)	C25—C26—H26	119.1
N1—C6—C7	112.6 (4)	C27—C26—H26	119.1
C5—C6—C7	111.5 (4)	C26—C27—C28	118.3 (6)
N1—C6—H6	111.9	C26—C27—H27	120.8
C5—C6—H6	111.9	C28—C27—H27	120.8
C7—C6—H6	111.9	C29—C28—C27	121.0 (7)
O8—C7—C6	110.7 (4)	C29—C28—H28	119.5
O8—C7—C8	109.1 (3)	C27—C28—H28	119.5
C6—C7—C8	112.1 (4)	C28—C29—C30	120.8 (6)
O8—C7—H7	108.2	C28—C29—H29	119.6
C6—C7—H7	108.2	C30—C29—H29	119.6
C8—C7—H7	108.2	C29—C30—C25	119.7 (6)
C15—C8—C7	112.9 (4)	C29—C30—H30	120.1
C15—C8—C9	114.3 (4)	C25—C30—H30	120.1
C7—C8—C9	106.9 (3)	O6—C31—O5	121.3 (7)
C15—C8—C14	112.4 (4)	O6—C31—C32	126.6 (7)
C7—C8—C14	111.7 (4)	O5—C31—C32	112.2 (7)
C9—C8—C14	97.5 (4)	C31—C32—H32A	109.5
C8—C9—C11	105.2 (4)	C31—C32—H32B	109.5
C8—C9—C10	101.3 (4)	H32A—C32—H32B	109.5
C11—C9—C10	123.4 (4)	C31—C32—H32C	109.5
C8—C9—H9	108.6	H32A—C32—H32C	109.5
C11—C9—H9	108.6	H32B—C32—H32C	109.5
C10—C9—H9	108.6	O9—C33—O8	122.9 (6)
C1—C10—C20	118.1 (4)	O9—C33—C34	126.7 (6)
C1—C10—C5	111.2 (4)	O8—C33—C34	110.4 (6)
C20—C10—C5	102.8 (4)	C33—C34—H34A	109.5
C1—C10—C9	114.3 (4)	C33—C34—H34B	109.5
C20—C10—C9	103.7 (4)	H34A—C34—H34B	109.5
C5—C10—C9	105.2 (4)	C33—C34—H34C	109.5
O10—C11—C12	110.0 (4)	H34A—C34—H34C	109.5
O10—C11—C9	113.6 (4)	H34B—C34—H34C	109.5
C12—C11—C9	111.0 (4)	O11—C35—O10	122.4 (6)
O10—C11—H11	107.3	O11—C35—C36	124.1 (6)
C12—C11—H11	107.3	O10—C35—C36	113.4 (6)
C9—C11—H11	107.3	C35—C36—H36A	109.5
C13—C12—C16	105.4 (4)	C35—C36—H36B	109.5
C13—C12—C11	111.5 (4)	H36A—C36—H36B	109.5
C16—C12—C11	106.4 (4)	C35—C36—H36C	109.5
C13—C12—H12	111.1	H36A—C36—H36C	109.5
C16—C12—H12	111.1	H36B—C36—H36C	109.5
C11—C12—H12	111.1	O13—C37—O12	122.4 (6)
O12—C13—C12	107.5 (4)	O13—C37—C38	125.2 (6)
O12—C13—C14	112.9 (4)	O12—C37—C38	112.5 (6)
C12—C13—C14	109.7 (4)	C39—C38—C43	120.2 (6)
O12—C13—H13	108.9	C39—C38—C37	117.5 (6)
C12—C13—H13	108.9	C43—C38—C37	122.2 (6)
C14—C13—H13	108.9	C38—C39—C40	119.6 (7)
C20—C14—C13	114.2 (4)	C38—C39—H39	120.2
C20—C14—C8	100.8 (3)	C40—C39—H39	120.2
C13—C14—C8	110.5 (4)	C41—C40—C39	119.1 (8)
C20—C14—H14	110.3	C41—C40—H40	120.4
C13—C14—H14	110.3	C39—C40—H40	120.4
C8—C14—H14	110.3	C40—C41—C42	122.4 (8)
C16—C15—C8	109.9 (4)	C40—C41—H41	118.8
C16—C15—H15A	109.7	C42—C41—H41	118.8
C8—C15—H15A	109.7	C41—C42—C43	118.0 (8)
C16—C15—H15B	109.7	C41—C42—H42	121.0
C8—C15—H15B	109.7	C43—C42—H42	121.0
H15A—C15—H15B	108.2	C38—C43—C42	120.6 (7)
C17—C16—C15	127.0 (6)	C38—C43—H43	119.7
C17—C16—C12	120.8 (5)	C42—C43—H43	119.7
C15—C16—C12	111.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O11ⁱ	0.89	2.38	3.205 (15)	155
O1W—H1B···O6	0.90	2.39	3.208 (15)	151
C15—H15A···O4ⁱⁱ	0.97	2.48	3.359 (8)	150
C23—H23B···O1W	0.96	2.58	3.491 (17)	159
C29—H29···O7ⁱⁱⁱ	0.93	2.40	3.290 (8)	160

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

Experimental details

Crystal data
Chemical formula	C₄₃H₄₆NO₁₃·0.5H₂O
M_r	793.82
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	292
a, b, c (Å)	11.517 (3), 18.045 (4), 19.241 (4)
V (Å³)	3998.7 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.52 × 0.46 × 0.42

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4333, 4092, 2220
R_int	0.007
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.150, 1.00
No. of reflections	4092
No. of parameters	530
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O11ⁱ	0.89	2.38	3.205 (15)	155
O1W—H1B···O6	0.90	2.39	3.208 (15)	151
C15—H15A···O4ⁱⁱ	0.97	2.48	3.359 (8)	150
C23—H23B···O1W	0.96	2.58	3.491 (17)	159
C29—H29···O7ⁱⁱⁱ	0.93	2.40	3.290 (8)	160

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

Acknowledgements

This project was supported by grants from the Department of Science and Technology of Sichuan Province, China (grant No. 05JY029), and the Scientific Research Fund of Leshan Teachers' College, China (grant No. Z07061).

References

Deng, Y. P., Chen, D. H. & Sun, W. L. (1992). Acta Chim. Sinica, 50, 822–826. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. Abstract PA104. American Crystallographic Association Meeting, Pittsburgh, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

(1β,2α,3α,7α,11α,13β)-1,3,7,11-Tetra­acet­­oxy-2,13-bis­­(benz­yl­oxy)-21-methyl-19,21-secohetisan-19-al hemi­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1β,2α,3α,7α,11α,13β)-1,3,7,11-Tetraacetoxy-2,13-bis(benzyloxy)-21-methyl-19,21-secohetisan-19-al hemihydrate