13-Ethoxy­carbonyl-16-(1-methyl­ethyl)-17,19-dinoratis-15-ene-4,14-dicarboxylic acid monohydrate: a new derivative of maleopimaric acid

Zhang, M.; Guo, X.; Zhou, Y.; Liu, H.

doi:10.1107/S1600536809028141

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1959

doi:10.1107/S1600536809028141

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13-Ethoxycarbonyl-16-(1-methylethyl)-17,19-dinoratis-15-ene-4,14-dicarboxylic acid monohydrate: a new derivative of maleopimaric acid

Meng Zhang,^a Xiao-xin Guo,^a Yong-hong Zhou ^a ^* and Hong-jun Liu ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
^*Correspondence e-mail: zm205@sohu.com

(Received 15 June 2009; accepted 17 July 2009; online 22 July 2009)

The title compound, C₂₆H₃₈O₆·H₂O, is a mono-ester of a derivative of maleopimaric acid, an abietic-type acid. The two fused and unbridged cyclohexane rings adopt approximate chair conformations while the three other three six-membered rings have boat conformations.

Related literature

Abietic type resin acid, the major component of gum rosin, is a high quality biomass resource for the development of new chiral drugs, see: McCoy (2000 ); Schweizer et al. (2003 ). For the use of abietic acid and its derivatives in the design and synthesis of industrially and physiologically important products, see: Savluchinske-Feio et al. (2007 ). For the structures of other maleopimaric acid derivatives, see: Li et al. (2005 ); Pan et al. (2006 ); Rao et al. (2006 ).

Experimental

Crystal data

C₂₆H₃₈O₆·H₂O
M_r = 464.58
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3406 (14) Å
b = 17.901 (4) Å
c = 19.681 (4) Å
V = 2586.2 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.98, T_max = 0.98
14084 measured reflections
2892 independent reflections
2318 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.113
S = 1.08
2892 reflections
303 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028141/bh2234sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028141/bh2234Isup2.hkl

checkCIF report

Comment top

Rosin, a versatile natural resin, possesses a rare combination of many desirable properties and has consequently found innumerable industrial uses in a modified form or in conjunction with other natural or synthetic resins. Abietic type resin acid is the major component of gum rosin, including abietic acid, neoabietic acid, levo-pimaric acid, palustric acid, and is a high quality biomass resource in developing chiral new drug (McCoy, 2000; Schweizer et al., 2003).

Abietic acid and its derivatives are readily available hydrophenanthrene compounds which become useful starting materials for the design and synthesis of industrially and physiologically important productions (Savluchinske-Feio et al., 2007). The crystal structures of other derivatives of maleopimaric acid have already been published (Rao et al., 2006; Li et al., 2005; Pan et al., 2006).

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit consists of two molecules, viz. maleopimaric ester derivative and one lattice water molecule. The cyclohexane rings C2···C5/C10/C11 and C1/C2/C11···C14 have typical chair forms. The cyclohexane ring C5···C10 has a slightly distorted boat conformation; the other two six-membered rings adopt boat conformations. The configuration about the C17C18 bond is Z (Fig. 1), with the H atom and the isopropyl group cis with respect to each other. The bond lengths and angles have normal values.

In the crystal structure, the molecules are linked (Fig. 2) by O—H···O and C—H···O intermolecular hydrogen bonds.

Related literature top

Abietic type resin acid, the major component of gum rosin, is a high quality biomass resource in the development of new chiral drugs, see: McCoy (2000); Schweizer et al. (2003). For the use of abietic acid and its derivatives in the design and synthesis of industrially and physiologically important products, see: Savluchinske-Feio et al. (2007). For the structures of other maleopimaric acid derivatives, see: Li et al. (2005); Pan et al. (2006); Rao et al. (2006).

Experimental top

Abietic acid (30.2 g), acetic acid (20 ml), and maleic acid ethyl ester (14.4 g) were put into a 100-ml three-necked flask and magnetically stirred; the mixture was stirred for 25 min. The solution was then put into 5 ml of glacial acetic acid and cooled, washed with hot water (10 ml), dried (MgSO₄), and concentrated to dryness. Recrystallization from ethanol (95%) afforded the adduct (33.9 g, 73%).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed along the a axis. Dashed lines indicate hydrogen bonds.

13-Ethoxycarbonyl-16-(1-methylethyl)-17,19-dinoratis-15-ene-4,14- dicarboxylic acid monohydrate top

Crystal data top

C₂₆H₃₈O₆·H₂O	D_x = 1.193 Mg m⁻³
M_r = 464.58	Melting point: 412 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2351 reflections
a = 7.3406 (14) Å	θ = 2.4–23.1°
b = 17.901 (4) Å	µ = 0.09 mm⁻¹
c = 19.681 (4) Å	T = 291 K
V = 2586.2 (9) Å³	Aciculae, colorless
Z = 4	0.26 × 0.22 × 0.20 mm
F(000) = 1008

Data collection top

Bruker SMART APEX CCD diffractometer	2892 independent reflections
Radiation source: sealed tube	2318 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→9
T_min = 0.98, T_max = 0.98	k = −21→22
14084 measured reflections	l = −11→24

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.04P)² + 0.66P] where P = (F_o² + 2F_c²)/3
2892 reflections	(Δ/σ)_max < 0.001
303 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³
0 constraints

Crystal data top

C₂₆H₃₈O₆·H₂O	V = 2586.2 (9) Å³
M_r = 464.58	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3406 (14) Å	µ = 0.09 mm⁻¹
b = 17.901 (4) Å	T = 291 K
c = 19.681 (4) Å	0.26 × 0.22 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2892 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2318 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.98	R_int = 0.076
14084 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	Δρ_max = 0.19 e Å⁻³
2892 reflections	Δρ_min = −0.22 e Å⁻³
303 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1062 (5)	0.27241 (19)	0.17771 (18)	0.0339 (8)
C2	0.1205 (5)	0.18852 (19)	0.16317 (18)	0.0321 (8)
H2	0.0801	0.1643	0.2052	0.039*
C3	0.3180 (5)	0.1612 (2)	0.1530 (2)	0.0386 (9)
H3A	0.3605	0.1755	0.1082	0.046*
H3B	0.3968	0.1845	0.1864	0.046*
C4	0.3272 (5)	0.0766 (2)	0.1604 (2)	0.0377 (9)
H4A	0.3005	0.0636	0.2072	0.045*
H4B	0.4505	0.0603	0.1507	0.045*
C5	0.1958 (5)	0.03398 (19)	0.11385 (18)	0.0330 (8)
C6	0.1724 (6)	−0.0481 (2)	0.14105 (18)	0.0378 (9)
H6	0.1139	−0.0455	0.1858	0.045*
C7	0.0419 (5)	−0.0908 (2)	0.0922 (2)	0.0382 (9)
H7	−0.0692	−0.1011	0.1182	0.046*
C8	−0.0146 (5)	−0.0396 (2)	0.03338 (19)	0.0406 (9)
H8	−0.0907	−0.0669	0.0009	0.049*
C9	−0.1211 (5)	0.0256 (2)	0.06435 (19)	0.0416 (9)
H9A	−0.2277	0.0066	0.0878	0.050*
H9B	−0.1621	0.0587	0.0284	0.050*
C10	0.0003 (5)	0.07016 (19)	0.11538 (19)	0.0339 (8)
H10	−0.0491	0.0597	0.1607	0.041*
C11	−0.0061 (5)	0.1561 (2)	0.10698 (18)	0.0360 (8)
C12	−0.2015 (5)	0.1820 (2)	0.1218 (2)	0.0411 (9)
H12A	−0.2443	0.1576	0.1629	0.049*
H12B	−0.2799	0.1665	0.0848	0.049*
C13	−0.2173 (5)	0.2672 (2)	0.1309 (2)	0.0426 (9)
H13A	−0.1819	0.2918	0.0891	0.051*
H13B	−0.3430	0.2802	0.1404	0.051*
C14	−0.0966 (5)	0.2947 (2)	0.1888 (2)	0.0394 (9)
H14A	−0.1394	0.2737	0.2313	0.047*
H14B	−0.1057	0.3487	0.1919	0.047*
C15	0.1951 (6)	0.3238 (2)	0.1237 (2)	0.0407 (9)
H15A	0.2085	0.3732	0.1420	0.061*
H15B	0.1192	0.3256	0.0840	0.061*
H15C	0.3127	0.3045	0.1117	0.061*
C16	0.0475 (6)	0.1813 (2)	0.03444 (19)	0.0417 (9)
H16A	−0.0103	0.1494	0.0017	0.063*
H16B	0.1773	0.1782	0.0293	0.063*
H16C	0.0087	0.2319	0.0274	0.063*
C17	0.2593 (6)	0.0286 (2)	0.04130 (19)	0.0388 (9)
H17	0.3666	0.0512	0.0268	0.047*
C18	0.1540 (5)	−0.01020 (19)	−0.00112 (19)	0.0364 (8)
C19	0.1871 (5)	−0.0250 (2)	−0.07525 (19)	0.0433 (10)
H19	0.1618	−0.0780	−0.0832	0.052*
C20	0.0537 (6)	0.0199 (2)	−0.1194 (2)	0.0452 (10)
H20A	−0.0670	0.0156	−0.1010	0.068*
H20B	0.0552	0.0007	−0.1649	0.068*
H20C	0.0895	0.0715	−0.1197	0.068*
C21	0.3860 (6)	−0.0108 (2)	−0.0965 (2)	0.0467 (10)
H21A	0.4165	0.0406	−0.0883	0.070*
H21B	0.4001	−0.0217	−0.1440	0.070*
H21C	0.4654	−0.0424	−0.0706	0.070*
C22	0.1092 (6)	−0.1652 (2)	0.0662 (2)	0.0415 (9)
C23	0.2168 (6)	−0.2869 (2)	0.0970 (2)	0.0429 (9)
H23A	0.1186	−0.3141	0.0752	0.051*
H23B	0.3167	−0.2825	0.0650	0.051*
C24	0.2779 (6)	−0.3275 (2)	0.1586 (2)	0.0447 (10)
H24A	0.3775	−0.3011	0.1792	0.067*
H24B	0.3169	−0.3769	0.1462	0.067*
H24C	0.1789	−0.3309	0.1904	0.067*
C25	0.1958 (5)	0.2900 (2)	0.24603 (19)	0.0371 (8)
C26	0.3572 (5)	−0.0844 (2)	0.1500 (2)	0.0384 (9)
O1	0.2639 (4)	0.35119 (14)	0.25908 (13)	0.0424 (7)
H1B	0.3484	0.3602	0.2308	0.051*
O2	0.1860 (4)	0.23935 (14)	0.29190 (13)	0.0423 (7)
O3	0.4065 (4)	−0.09128 (14)	0.21215 (13)	0.0436 (7)
O4	0.4538 (4)	−0.10191 (15)	0.10165 (13)	0.0409 (6)
H4D	0.3978	−0.1341	0.0778	0.049*
O5	0.1529 (4)	−0.21151 (13)	0.11749 (13)	0.0391 (6)
O6	0.1159 (3)	−0.18329 (13)	0.00746 (14)	0.0408 (6)
O7	0.2953 (4)	0.28560 (15)	0.40900 (13)	0.0425 (6)
H7A	0.2924	0.3307	0.4224	0.051*
H7B	0.2238	0.2594	0.4333	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0347 (19)	0.0271 (17)	0.040 (2)	−0.0036 (16)	0.0019 (17)	−0.0020 (15)
C2	0.0265 (18)	0.0361 (19)	0.0337 (19)	−0.0052 (15)	−0.0003 (16)	−0.0016 (16)
C3	0.0275 (19)	0.040 (2)	0.048 (2)	0.0030 (16)	−0.0046 (18)	−0.0039 (17)
C4	0.0325 (19)	0.037 (2)	0.044 (2)	0.0000 (16)	−0.0080 (17)	−0.0032 (17)
C5	0.0271 (18)	0.0347 (19)	0.037 (2)	0.0018 (14)	0.0040 (16)	−0.0036 (16)
C6	0.048 (2)	0.038 (2)	0.0274 (19)	0.0047 (18)	0.0051 (17)	−0.0015 (15)
C7	0.035 (2)	0.0338 (19)	0.045 (2)	−0.0025 (16)	0.0062 (17)	−0.0028 (18)
C8	0.043 (2)	0.042 (2)	0.037 (2)	0.0004 (17)	−0.0015 (19)	−0.0089 (18)
C9	0.036 (2)	0.051 (2)	0.037 (2)	−0.0026 (18)	−0.0058 (18)	−0.0076 (18)
C10	0.0252 (17)	0.039 (2)	0.038 (2)	0.0000 (15)	0.0017 (17)	−0.0099 (16)
C11	0.0354 (19)	0.0377 (19)	0.035 (2)	−0.0004 (16)	0.0016 (18)	−0.0008 (16)
C12	0.0298 (19)	0.049 (2)	0.044 (2)	0.0025 (17)	−0.0049 (17)	−0.0099 (19)
C13	0.035 (2)	0.045 (2)	0.048 (2)	0.0020 (17)	−0.0037 (18)	−0.0020 (18)
C14	0.040 (2)	0.037 (2)	0.042 (2)	0.0057 (17)	0.0020 (18)	−0.0030 (17)
C15	0.041 (2)	0.039 (2)	0.042 (2)	−0.0034 (17)	0.0019 (18)	0.0011 (17)
C16	0.048 (2)	0.039 (2)	0.039 (2)	0.0049 (18)	−0.0066 (18)	0.0010 (17)
C17	0.041 (2)	0.036 (2)	0.040 (2)	0.0054 (17)	0.0039 (18)	−0.0010 (16)
C18	0.040 (2)	0.0335 (19)	0.0356 (19)	0.0076 (16)	−0.0004 (17)	0.0017 (17)
C19	0.042 (2)	0.053 (2)	0.035 (2)	0.0143 (19)	0.0014 (18)	0.0017 (18)
C20	0.047 (2)	0.046 (2)	0.043 (2)	0.0144 (18)	−0.0070 (19)	0.0063 (18)
C21	0.054 (3)	0.045 (2)	0.041 (2)	−0.0068 (19)	0.021 (2)	−0.0155 (19)
C22	0.048 (2)	0.032 (2)	0.044 (2)	−0.0064 (18)	0.005 (2)	−0.0064 (17)
C23	0.038 (2)	0.047 (2)	0.044 (2)	0.0031 (18)	0.0079 (19)	−0.0003 (19)
C24	0.042 (2)	0.046 (2)	0.046 (2)	0.0153 (19)	0.0146 (19)	0.0098 (18)
C25	0.038 (2)	0.037 (2)	0.0358 (19)	−0.0016 (17)	−0.0063 (17)	−0.0104 (17)
C26	0.045 (2)	0.0295 (19)	0.041 (2)	0.0031 (17)	0.0013 (18)	−0.0051 (16)
O1	0.0412 (15)	0.0444 (15)	0.0415 (15)	−0.0124 (13)	−0.0165 (13)	0.0077 (12)
O2	0.0409 (15)	0.0438 (15)	0.0423 (14)	−0.0094 (12)	−0.0090 (13)	0.0049 (12)
O3	0.0449 (16)	0.0410 (14)	0.0449 (16)	0.0214 (13)	−0.0168 (13)	−0.0026 (12)
O4	0.0414 (15)	0.0439 (16)	0.0375 (15)	0.0136 (12)	−0.0009 (12)	−0.0033 (12)
O5	0.0464 (15)	0.0319 (13)	0.0391 (14)	−0.0007 (12)	0.0035 (12)	−0.0011 (11)
O6	0.0421 (15)	0.0375 (14)	0.0429 (15)	0.0016 (12)	0.0042 (13)	−0.0123 (12)
O7	0.0413 (15)	0.0449 (15)	0.0413 (15)	−0.0066 (12)	−0.0096 (12)	0.0059 (13)

Geometric parameters (Å, º) top

C1—C25	1.530 (5)	C14—H14A	0.9700
C1—C2	1.532 (5)	C14—H14B	0.9700
C1—C15	1.550 (5)	C15—H15A	0.9600
C1—C14	1.557 (5)	C15—H15B	0.9600
C2—C3	1.543 (5)	C15—H15C	0.9600
C2—C11	1.557 (5)	C16—H16A	0.9600
C2—H2	0.9800	C16—H16B	0.9600
C3—C4	1.523 (5)	C16—H16C	0.9600
C3—H3A	0.9700	C17—C18	1.333 (5)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.533 (5)	C18—C19	1.503 (5)
C4—H4A	0.9700	C19—C20	1.535 (5)
C4—H4B	0.9700	C19—C21	1.540 (6)
C5—C17	1.505 (5)	C19—H19	0.9800
C5—C6	1.574 (5)	C20—H20A	0.9600
C5—C10	1.574 (5)	C20—H20B	0.9600
C6—C26	1.514 (5)	C20—H20C	0.9600
C6—C7	1.557 (5)	C21—H21A	0.9600
C6—H6	0.9800	C21—H21B	0.9600
C7—C22	1.510 (5)	C21—H21C	0.9600
C7—C8	1.534 (5)	C22—O6	1.201 (4)
C7—H7	0.9800	C22—O5	1.345 (5)
C8—C18	1.506 (5)	C23—C24	1.484 (5)
C8—C9	1.532 (5)	C23—O5	1.484 (5)
C8—H8	0.9800	C23—H23A	0.9700
C9—C10	1.562 (5)	C23—H23B	0.9700
C9—H9A	0.9700	C24—H24A	0.9600
C9—H9B	0.9700	C24—H24B	0.9600
C10—C11	1.548 (5)	C24—H24C	0.9600
C10—H10	0.9800	C25—O1	1.231 (4)
C11—C12	1.535 (5)	C25—O2	1.281 (4)
C11—C16	1.548 (5)	C26—O4	1.227 (4)
C12—C13	1.539 (5)	C26—O3	1.282 (4)
C12—H12A	0.9700	O1—H1B	0.8499
C12—H12B	0.9700	O4—H4D	0.8500
C13—C14	1.524 (5)	O7—H7A	0.8499
C13—H13A	0.9700	O7—H7B	0.8501
C13—H13B	0.9700

C25—C1—C2	109.6 (3)	C14—C13—H13A	109.4
C25—C1—C15	107.4 (3)	C12—C13—H13A	109.4
C2—C1—C15	115.1 (3)	C14—C13—H13B	109.4
C25—C1—C14	103.6 (3)	C12—C13—H13B	109.4
C2—C1—C14	110.1 (3)	H13A—C13—H13B	108.0
C15—C1—C14	110.2 (3)	C13—C14—C1	111.6 (3)
C1—C2—C3	113.6 (3)	C13—C14—H14A	109.3
C1—C2—C11	117.2 (3)	C1—C14—H14A	109.3
C3—C2—C11	110.5 (3)	C13—C14—H14B	109.3
C1—C2—H2	104.7	C1—C14—H14B	109.3
C3—C2—H2	104.7	H14A—C14—H14B	108.0
C11—C2—H2	104.7	C1—C15—H15A	109.5
C4—C3—C2	110.1 (3)	C1—C15—H15B	109.5
C4—C3—H3A	109.6	H15A—C15—H15B	109.5
C2—C3—H3A	109.6	C1—C15—H15C	109.5
C4—C3—H3B	109.6	H15A—C15—H15C	109.5
C2—C3—H3B	109.6	H15B—C15—H15C	109.5
H3A—C3—H3B	108.1	C11—C16—H16A	109.5
C3—C4—C5	114.2 (3)	C11—C16—H16B	109.5
C3—C4—H4A	108.7	H16A—C16—H16B	109.5
C5—C4—H4A	108.7	C11—C16—H16C	109.5
C3—C4—H4B	108.7	H16A—C16—H16C	109.5
C5—C4—H4B	108.7	H16B—C16—H16C	109.5
H4A—C4—H4B	107.6	C18—C17—C5	116.6 (4)
C17—C5—C4	113.8 (3)	C18—C17—H17	121.7
C17—C5—C6	107.3 (3)	C5—C17—H17	121.7
C4—C5—C6	109.3 (3)	C17—C18—C19	127.3 (4)
C17—C5—C10	109.1 (3)	C17—C18—C8	112.1 (3)
C4—C5—C10	110.9 (3)	C19—C18—C8	120.6 (3)
C6—C5—C10	106.2 (3)	C18—C19—C20	110.7 (3)
C26—C6—C7	114.4 (3)	C18—C19—C21	112.9 (3)
C26—C6—C5	110.0 (3)	C20—C19—C21	111.4 (4)
C7—C6—C5	108.4 (3)	C18—C19—H19	107.2
C26—C6—H6	108.0	C20—C19—H19	107.2
C7—C6—H6	108.0	C21—C19—H19	107.2
C5—C6—H6	108.0	C19—C20—H20A	109.5
C22—C7—C8	111.1 (3)	C19—C20—H20B	109.5
C22—C7—C6	116.1 (3)	H20A—C20—H20B	109.5
C8—C7—C6	109.8 (3)	C19—C20—H20C	109.5
C22—C7—H7	106.4	H20A—C20—H20C	109.5
C8—C7—H7	106.4	H20B—C20—H20C	109.5
C6—C7—H7	106.4	C19—C21—H21A	109.5
C18—C8—C9	109.4 (3)	C19—C21—H21B	109.5
C18—C8—C7	109.1 (3)	H21A—C21—H21B	109.5
C9—C8—C7	107.0 (3)	C19—C21—H21C	109.5
C18—C8—H8	110.4	H21A—C21—H21C	109.5
C9—C8—H8	110.4	H21B—C21—H21C	109.5
C7—C8—H8	110.4	O6—C22—O5	123.1 (3)
C8—C9—C10	110.7 (3)	O6—C22—C7	125.3 (4)
C8—C9—H9A	109.5	O5—C22—C7	111.5 (3)
C10—C9—H9A	109.5	C24—C23—O5	108.6 (3)
C8—C9—H9B	109.5	C24—C23—H23A	110.0
C10—C9—H9B	109.5	O5—C23—H23A	110.0
H9A—C9—H9B	108.1	C24—C23—H23B	110.0
C11—C10—C9	114.9 (3)	O5—C23—H23B	110.0
C11—C10—C5	115.8 (3)	H23A—C23—H23B	108.3
C9—C10—C5	107.3 (3)	C23—C24—H24A	109.5
C11—C10—H10	106.0	C23—C24—H24B	109.5
C9—C10—H10	106.0	H24A—C24—H24B	109.5
C5—C10—H10	106.0	C23—C24—H24C	109.5
C12—C11—C16	109.0 (3)	H24A—C24—H24C	109.5
C12—C11—C10	107.9 (3)	H24B—C24—H24C	109.5
C16—C11—C10	112.3 (3)	O1—C25—O2	120.3 (3)
C12—C11—C2	108.1 (3)	O1—C25—C1	122.7 (3)
C16—C11—C2	113.3 (3)	O2—C25—C1	116.7 (3)
C10—C11—C2	106.0 (3)	O4—C26—O3	123.5 (4)
C11—C12—C13	113.0 (3)	O4—C26—C6	122.5 (4)
C11—C12—H12A	109.0	O3—C26—C6	113.9 (3)
C13—C12—H12A	109.0	C25—O1—H1B	109.1
C11—C12—H12B	109.0	C26—O4—H4D	108.8
C13—C12—H12B	109.0	C22—O5—C23	115.6 (3)
H12A—C12—H12B	107.8	H7A—O7—H7B	109.5
C14—C13—C12	111.3 (3)

C25—C1—C2—C3	−65.4 (4)	C3—C2—C11—C12	177.2 (3)
C15—C1—C2—C3	55.8 (4)	C1—C2—C11—C16	70.3 (4)
C14—C1—C2—C3	−178.8 (3)	C3—C2—C11—C16	−61.9 (4)
C25—C1—C2—C11	163.8 (3)	C1—C2—C11—C10	−166.1 (3)
C15—C1—C2—C11	−75.0 (4)	C3—C2—C11—C10	61.7 (4)
C14—C1—C2—C11	50.4 (4)	C16—C11—C12—C13	−70.6 (4)
C1—C2—C3—C4	162.8 (3)	C10—C11—C12—C13	167.2 (3)
C11—C2—C3—C4	−63.2 (4)	C2—C11—C12—C13	52.9 (4)
C2—C3—C4—C5	54.5 (4)	C11—C12—C13—C14	−58.7 (4)
C3—C4—C5—C17	77.7 (4)	C12—C13—C14—C1	56.6 (4)
C3—C4—C5—C6	−162.5 (3)	C25—C1—C14—C13	−168.7 (3)
C3—C4—C5—C10	−45.8 (4)	C2—C1—C14—C13	−51.5 (4)
C17—C5—C6—C26	70.7 (4)	C15—C1—C14—C13	76.6 (4)
C4—C5—C6—C26	−53.1 (4)	C4—C5—C17—C18	177.6 (3)
C10—C5—C6—C26	−172.8 (3)	C6—C5—C17—C18	56.6 (4)
C17—C5—C6—C7	−55.0 (4)	C10—C5—C17—C18	−57.9 (4)
C4—C5—C6—C7	−178.8 (3)	C5—C17—C18—C19	−179.1 (3)
C10—C5—C6—C7	61.5 (4)	C5—C17—C18—C8	1.6 (5)
C26—C6—C7—C22	5.7 (5)	C9—C8—C18—C17	57.1 (4)
C5—C6—C7—C22	128.8 (3)	C7—C8—C18—C17	−59.7 (4)
C26—C6—C7—C8	−121.4 (3)	C9—C8—C18—C19	−122.3 (4)
C5—C6—C7—C8	1.8 (4)	C7—C8—C18—C19	120.9 (3)
C22—C7—C8—C18	−74.8 (4)	C17—C18—C19—C20	−108.6 (4)
C6—C7—C8—C18	55.0 (4)	C8—C18—C19—C20	70.7 (5)
C22—C7—C8—C9	166.9 (3)	C17—C18—C19—C21	17.0 (6)
C6—C7—C8—C9	−63.3 (4)	C8—C18—C19—C21	−163.7 (3)
C18—C8—C9—C10	−57.4 (4)	C8—C7—C22—O6	−1.2 (6)
C7—C8—C9—C10	60.7 (4)	C6—C7—C22—O6	−127.6 (4)
C8—C9—C10—C11	133.3 (3)	C8—C7—C22—O5	−177.8 (3)
C8—C9—C10—C5	3.0 (4)	C6—C7—C22—O5	55.8 (4)
C17—C5—C10—C11	−78.5 (4)	C2—C1—C25—O1	152.3 (4)
C4—C5—C10—C11	47.7 (4)	C15—C1—C25—O1	26.5 (5)
C6—C5—C10—C11	166.3 (3)	C14—C1—C25—O1	−90.2 (4)
C17—C5—C10—C9	51.4 (4)	C2—C1—C25—O2	−32.6 (4)
C4—C5—C10—C9	177.5 (3)	C15—C1—C25—O2	−158.4 (3)
C6—C5—C10—C9	−63.9 (4)	C14—C1—C25—O2	84.9 (4)
C9—C10—C11—C12	63.4 (4)	C7—C6—C26—O4	52.3 (5)
C5—C10—C11—C12	−170.5 (3)	C5—C6—C26—O4	−69.9 (4)
C9—C10—C11—C16	−56.8 (4)	C7—C6—C26—O3	−131.2 (3)
C5—C10—C11—C16	69.3 (4)	C5—C6—C26—O3	106.5 (4)
C9—C10—C11—C2	179.0 (3)	O6—C22—O5—C23	2.0 (5)
C5—C10—C11—C2	−54.9 (4)	C7—C22—O5—C23	178.7 (3)
C1—C2—C11—C12	−50.6 (4)	C24—C23—O5—C22	173.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4D···O5	0.85	2.40	2.971 (4)	125
O7—H7B···O6ⁱ	0.85	2.32	2.745 (4)	111
C2—H2···O2	0.98	2.31	2.735 (4)	105
C15—H15A···O1	0.96	2.37	2.756 (5)	103

Symmetry code: (i) −x+1/2, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₈O₆·H₂O
M_r	464.58
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	291
a, b, c (Å)	7.3406 (14), 17.901 (4), 19.681 (4)
V (Å³)	2586.2 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.98, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	14084, 2892, 2318
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.113, 1.08
No. of reflections	2892
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the President of the Chinese Academy of Forestry Foundation (CAFYBB2008009).

References

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