16-Isopropyl-5,9-dimethyl­tetra­cyclo­[10.2.2.01,10.04,9]hexa­dec-15-ene-5,13,14-trimethanol ethanol monosolvate

Li, J.; Rao, X.; Shang, S.; Gao, Y.

doi:10.1107/S1600536811012207

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1076

doi:10.1107/S1600536811012207

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16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.0^1,10.0^4,9]hexadec-15-ene-5,13,14-trimethanol ethanol monosolvate

Jian Li,^a Xiao-ping Rao,^a Shi-bin Shang ^a ^* and Yan-qing Gao ^a

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

(Received 4 March 2011; accepted 1 April 2011; online 7 April 2011)

The title compound, C₂₄H₄₀O₃·C₂H₆O, is a substituted tetracyclo[10.2.2.0^1,10.0^4,9]hexadecane derivative obtained from the reduction of maleopimaric acid which was isolated from a maleic anhydride modified rosin. In the crystal, the triol molecule and the ethanol solvent molecule are linked by hydroxyl O—H⋯O hydrogen bonds, giving a two-dimensional network structure.

Related literature

For the isolation of maleic anhydride modified rosin, see: Halbrook & Lawrence (1958 ). For the crystal structure of maleopimaric acid, see: Rao et al. (2008 ).

Experimental

Crystal data

C₂₄H₄₀O₃·C₂H₆O
M_r = 422.63
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1440 (18) Å
b = 9.6570 (19) Å
c = 28.073 (6) Å
V = 2478.9 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 four-circle diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.978, T_max = 0.993
4919 measured reflections
2615 independent reflections
1786 reflections with I > 2σ(I)
R_int = 0.076
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.180
S = 1.00
2615 reflections
271 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.85	2.27	2.749 (5)	116
O3—H3A⋯O1ⁱ	0.82	1.97	2.758 (5)	160
O4—H4C⋯O2ⁱⁱ	0.85	1.90	2.704 (6)	157
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012207/zs2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012207/zs2101Isup2.hkl

checkCIF report

Comment top

As an important natural resource, large amounts of rosin are available in China. Nowadays, rosin and its Diels-Alder adducts have been developed as a feedstock for synthesizing various chemicals and intermediates. Maleopimaric acid was isolated from maleic anhydride modified rosin (Halbrook & Lawrence, 1958), and its crystal structure has been reported (Rao et al., 2008). The title compound C₂₄H₄₀O₃ . C₂H₆O (I) was obtained on reduction of this tricarboxylic acid. The asymmetric unit comprises a triol molecule and an ethanol molecule of solvation (Fig. 1). In the crystal structure the molecules are linked by hydroxyl O–H···O hydrogen bonds and other interactions (Table 1, Fig. 2), giving a two-dimensional network structure. The absolute configurations for the 8 chiral centres in this molecule could not be assigned from the analysis: the configurations for the chosen enantiomer were C1(R), C5(R), C6(R), C7(R), C8(S), C12(R), C13(R), C14(R).

Related literature top

For the isolation of maleic anhydride modified rosin, see: Halbrook & Lawrence (1958). For the crystal structure of maleopimaric acid, see: Rao et al. (2008).

Experimental top

Maleopimaric acid (12.0 g) was dissolved in tetrahydrofuran (300 ml) at 263 K while stirring vigorously and lithium aluminium hydride (6.9 g) was added over a period of 2 h. The reaction was maintained for 1 h at reflux temperature after which water (6.9 ml) and 10% sodium hydroxide solution (6.9 ml) were added dropwise at 263 K. The mixture was filtered and the filtrate was concentrated, giving the crude product which was recrystallized with ethanol, giving the title compound. Crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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

	Fig. 1. Molecular conformation and atom numbering scheme for (I), showing displacement ellipsoids at the 30% probability level.
	Fig. 2. A view of the packing of the title compound in the unit cell, with hydrogen bonds shown as dashed lines.

16-isopropyl-5,9-dimethyltetracyclo[10.2.2.0^1,10.0^4,9]hexadec-15-ene- 5,13,14-trimethanol ethanol monosolvate top

Crystal data top

C₂₄H₄₀O₃·C₂H₆O	F(000) = 936
M_r = 422.63	D_x = 1.132 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.1440 (18) Å	θ = 9–13°
b = 9.6570 (19) Å	µ = 0.07 mm⁻¹
c = 28.073 (6) Å	T = 293 K
V = 2478.9 (9) Å³	Rod, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 four-circle diffractometer	1786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.076
Graphite monochromator	θ_max = 25.4°, θ_min = 1.5°
ω–2θ scans	h = −11→0
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.978, T_max = 0.993	l = −33→0
4919 measured reflections	3 standard reflections every 200 reflections
2615 independent reflections	intensity decay: 1%

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.10P)² + 0.50P] where P = (F_o² + 2F_c²)/3
2615 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.29 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₄H₄₀O₃·C₂H₆O	V = 2478.9 (9) Å³
M_r = 422.63	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1440 (18) Å	µ = 0.07 mm⁻¹
b = 9.6570 (19) Å	T = 293 K
c = 28.073 (6) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 four-circle diffractometer	1786 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.076
T_min = 0.978, T_max = 0.993	3 standard reflections every 200 reflections
4919 measured reflections	intensity decay: 1%
2615 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	1 restraint
wR(F²) = 0.180	H-atom parameters constrained
S = 1.00	Δρ_max = 0.29 e Å⁻³
2615 reflections	Δρ_min = −0.22 e Å⁻³
271 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	0.1259 (4)	0.9737 (4)	0.16607 (12)	0.0551 (10)
H1A	0.1038	0.8921	0.1748	0.083*
C1	0.1816 (5)	0.8655 (5)	0.08762 (16)	0.0379 (12)
O2	0.6060 (4)	0.0733 (3)	0.19112 (12)	0.0476 (9)
H2A	0.5244	0.0514	0.1787	0.071*
C2	0.0246 (6)	0.8104 (5)	0.08231 (19)	0.0480 (14)
H2B	−0.0204	0.8058	0.1136	0.058*
H2C	−0.0315	0.8752	0.0632	0.058*
O3	0.6437 (4)	0.4603 (4)	0.27068 (12)	0.0512 (9)
H3A	0.7228	0.4721	0.2839	0.077*
C3	0.0171 (6)	0.6667 (6)	0.05903 (19)	0.0491 (14)
H3B	−0.0838	0.6358	0.0578	0.059*
H3C	0.0538	0.6719	0.0267	0.059*
C4	0.1076 (5)	0.5638 (5)	0.08736 (18)	0.0435 (12)
H4A	0.1013	0.4738	0.0721	0.052*
H4B	0.0661	0.5551	0.1190	0.052*
C5	0.2677 (5)	0.6040 (5)	0.09188 (16)	0.0335 (11)
C6	0.2777 (5)	0.7538 (4)	0.11185 (16)	0.0329 (11)
H6A	0.2382	0.7466	0.1442	0.039*
C7	0.3387 (5)	0.5085 (4)	0.12991 (16)	0.0330 (10)
H7A	0.2768	0.5169	0.1583	0.040*
C8	0.4957 (5)	0.5467 (4)	0.14670 (14)	0.0290 (10)
C9	0.5092 (5)	0.7028 (5)	0.15633 (17)	0.0361 (11)
H9A	0.4657	0.7229	0.1871	0.043*
H9B	0.6121	0.7266	0.1582	0.043*
C10	0.4373 (5)	0.7937 (5)	0.11907 (17)	0.0365 (11)
H10A	0.4894	0.7846	0.0891	0.044*
H10B	0.4430	0.8898	0.1290	0.044*
C11	0.3361 (5)	0.3518 (4)	0.11655 (18)	0.0390 (12)
H11A	0.2590	0.3054	0.1341	0.047*
H11B	0.3160	0.3415	0.0828	0.047*
C12	0.4843 (6)	0.2851 (5)	0.12847 (18)	0.0396 (12)
H12A	0.4837	0.1867	0.1200	0.048*
C13	0.5099 (5)	0.3032 (5)	0.18254 (16)	0.0345 (11)
H13A	0.4229	0.2675	0.1988	0.041*
C14	0.5201 (5)	0.4612 (5)	0.19389 (15)	0.0343 (11)
H14A	0.4356	0.4818	0.2142	0.041*
C15	0.6011 (6)	0.3603 (5)	0.10101 (17)	0.0418 (12)
C16	0.6064 (5)	0.4944 (5)	0.11130 (16)	0.0369 (11)
H16A	0.6748	0.5530	0.0974	0.044*
C17	0.2395 (7)	0.9152 (6)	0.03954 (18)	0.0601 (16)
H17A	0.2460	0.8381	0.0180	0.090*
H17B	0.3346	0.9554	0.0437	0.090*
H17C	0.1741	0.9834	0.0266	0.090*
C18	0.1740 (6)	0.9966 (5)	0.11865 (19)	0.0495 (13)
H18A	0.2704	1.0385	0.1197	0.059*
H18B	0.1084	1.0622	0.1036	0.059*
C19	0.3445 (6)	0.5886 (5)	0.04277 (16)	0.0466 (13)
H19A	0.3362	0.4945	0.0321	0.070*
H19B	0.4459	0.6126	0.0458	0.070*
H19C	0.2988	0.6490	0.0201	0.070*
C20	0.6958 (7)	0.2905 (6)	0.06440 (19)	0.0571 (15)
H20A	0.7557	0.3625	0.0494	0.069*
C21	0.5967 (10)	0.2283 (7)	0.0251 (2)	0.086 (2)
H21A	0.5324	0.2987	0.0131	0.129*
H21B	0.5399	0.1539	0.0382	0.129*
H21C	0.6564	0.1937	−0.0004	0.129*
C22	0.7994 (9)	0.1842 (9)	0.0851 (2)	0.108 (3)
H22A	0.8570	0.2262	0.1098	0.161*
H22B	0.8628	0.1502	0.0605	0.161*
H22C	0.7443	0.1087	0.0982	0.161*
C23	0.6387 (6)	0.2176 (5)	0.19917 (18)	0.0400 (11)
H23A	0.7259	0.2438	0.1817	0.048*
H23B	0.6563	0.2338	0.2328	0.048*
C24	0.6531 (6)	0.5052 (5)	0.22226 (17)	0.0460 (13)
H24A	0.7403	0.4664	0.2078	0.055*
H24B	0.6616	0.6053	0.2214	0.055*
O4	0.8584 (5)	0.9317 (6)	0.20316 (18)	0.0869 (15)
H4C	0.7882	0.9888	0.2061	0.130*
C25	0.8793 (10)	0.8696 (12)	0.2457 (4)	0.157 (5)
H25A	0.7847	0.8333	0.2551	0.189*
H25B	0.9021	0.9432	0.2680	0.189*
C26	0.9818 (13)	0.7624 (13)	0.2547 (6)	0.222 (8)
H26A	0.9793	0.7386	0.2879	0.333*
H26B	1.0782	0.7937	0.2464	0.333*
H26C	0.9574	0.6826	0.2360	0.333*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.055 (2)	0.058 (2)	0.052 (2)	0.006 (2)	−0.0004 (18)	−0.0159 (18)
C1	0.045 (3)	0.034 (2)	0.034 (3)	0.006 (2)	−0.008 (2)	0.004 (2)
O2	0.045 (2)	0.0382 (18)	0.059 (2)	0.0058 (18)	−0.0007 (18)	0.0046 (16)
C2	0.051 (3)	0.044 (3)	0.049 (3)	0.011 (3)	−0.013 (3)	−0.003 (2)
O3	0.055 (2)	0.057 (2)	0.042 (2)	0.005 (2)	−0.0229 (17)	0.0004 (17)
C3	0.035 (3)	0.058 (3)	0.054 (3)	−0.001 (3)	−0.014 (2)	−0.006 (3)
C4	0.043 (3)	0.039 (3)	0.049 (3)	−0.002 (2)	−0.008 (2)	0.000 (2)
C5	0.036 (3)	0.033 (2)	0.032 (2)	−0.002 (2)	−0.003 (2)	−0.003 (2)
C6	0.039 (3)	0.031 (2)	0.028 (2)	0.002 (2)	0.000 (2)	0.001 (2)
C7	0.036 (2)	0.028 (2)	0.036 (2)	−0.002 (2)	−0.002 (2)	−0.0007 (19)
C8	0.031 (2)	0.030 (2)	0.025 (2)	−0.001 (2)	0.0003 (19)	−0.0025 (19)
C9	0.036 (3)	0.031 (2)	0.041 (3)	0.000 (2)	−0.011 (2)	−0.005 (2)
C10	0.042 (3)	0.028 (2)	0.040 (3)	−0.003 (2)	0.000 (2)	−0.001 (2)
C11	0.041 (3)	0.031 (2)	0.046 (3)	−0.001 (2)	−0.005 (2)	−0.004 (2)
C12	0.048 (3)	0.024 (2)	0.047 (3)	0.003 (2)	−0.007 (2)	−0.008 (2)
C13	0.034 (3)	0.032 (2)	0.038 (3)	−0.002 (2)	−0.001 (2)	0.003 (2)
C14	0.036 (3)	0.036 (2)	0.030 (2)	0.002 (2)	0.004 (2)	−0.001 (2)
C15	0.045 (3)	0.043 (3)	0.037 (3)	0.014 (2)	−0.004 (2)	0.002 (2)
C16	0.031 (2)	0.043 (3)	0.037 (3)	0.003 (2)	0.000 (2)	0.006 (2)
C17	0.078 (4)	0.055 (3)	0.047 (3)	0.013 (3)	−0.001 (3)	0.017 (3)
C18	0.049 (3)	0.041 (3)	0.059 (3)	0.008 (2)	−0.009 (3)	−0.002 (3)
C19	0.056 (3)	0.049 (3)	0.035 (3)	0.009 (3)	−0.005 (2)	−0.004 (2)
C20	0.071 (4)	0.056 (3)	0.044 (3)	0.014 (3)	0.011 (3)	−0.001 (3)
C21	0.125 (7)	0.080 (5)	0.053 (4)	0.012 (5)	0.017 (4)	−0.022 (4)
C22	0.125 (7)	0.125 (7)	0.073 (5)	0.082 (6)	0.028 (5)	0.005 (5)
C23	0.044 (3)	0.036 (2)	0.040 (3)	0.005 (2)	−0.003 (2)	0.002 (2)
C24	0.049 (3)	0.049 (3)	0.040 (3)	−0.003 (3)	−0.016 (2)	0.004 (2)
O4	0.058 (3)	0.100 (3)	0.103 (4)	0.033 (3)	0.011 (3)	0.024 (3)
C25	0.092 (7)	0.185 (11)	0.194 (11)	0.032 (8)	0.064 (8)	0.100 (10)
C26	0.098 (8)	0.212 (15)	0.356 (18)	−0.024 (9)	−0.054 (10)	0.189 (14)

Geometric parameters (Å, º) top

O1—C18	1.419 (6)	C12—C13	1.546 (6)
O1—H1A	0.8500	C12—H12A	0.9800
C1—C17	1.527 (7)	C13—C23	1.512 (6)
C1—C18	1.538 (7)	C13—C14	1.561 (6)
C1—C2	1.539 (7)	C13—H13A	0.9800
C1—C6	1.549 (6)	C14—C24	1.515 (6)
O2—C23	1.444 (6)	C14—H14A	0.9800
O2—H2A	0.8500	C15—C16	1.327 (7)
C2—C3	1.536 (7)	C15—C20	1.504 (7)
C2—H2B	0.9700	C16—H16A	0.9300
C2—H2C	0.9700	C17—H17A	0.9600
O3—C24	1.429 (6)	C17—H17B	0.9600
O3—H3A	0.8200	C17—H17C	0.9600
C3—C4	1.518 (7)	C18—H18A	0.9700
C3—H3B	0.9700	C18—H18B	0.9700
C3—H3C	0.9700	C19—H19A	0.9600
C4—C5	1.521 (7)	C19—H19B	0.9600
C4—H4A	0.9700	C19—H19C	0.9600
C4—H4B	0.9700	C20—C22	1.513 (9)
C5—C7	1.553 (6)	C20—C21	1.549 (9)
C5—C6	1.553 (6)	C20—H20A	0.9800
C5—C19	1.554 (6)	C21—H21A	0.9600
C6—C10	1.523 (6)	C21—H21B	0.9600
C6—H6A	0.9800	C21—H21C	0.9600
C7—C8	1.555 (6)	C22—H22A	0.9600
C7—C11	1.559 (6)	C22—H22B	0.9600
C7—H7A	0.9800	C22—H22C	0.9600
C8—C16	1.505 (6)	C23—H23A	0.9700
C8—C9	1.537 (6)	C23—H23B	0.9700
C8—C14	1.577 (6)	C24—H24A	0.9700
C9—C10	1.516 (6)	C24—H24B	0.9700
C9—H9A	0.9700	O4—C25	1.349 (10)
C9—H9B	0.9700	O4—H4C	0.8500
C10—H10A	0.9700	C25—C26	1.420 (9)
C10—H10B	0.9700	C25—H25A	0.9700
C11—C12	1.538 (7)	C25—H25B	0.9700
C11—H11A	0.9700	C26—H26A	0.9600
C11—H11B	0.9700	C26—H26B	0.9600
C12—C15	1.504 (7)	C26—H26C	0.9600

C18—O1—H1A	119.2	C12—C13—C14	108.6 (4)
C17—C1—C18	104.9 (4)	C23—C13—H13A	107.2
C17—C1—C2	110.3 (4)	C12—C13—H13A	107.2
C18—C1—C2	107.3 (4)	C14—C13—H13A	107.2
C17—C1—C6	114.3 (4)	C24—C14—C13	115.4 (4)
C18—C1—C6	110.5 (4)	C24—C14—C8	114.1 (4)
C2—C1—C6	109.3 (4)	C13—C14—C8	109.4 (3)
C23—O2—H2A	119.1	C24—C14—H14A	105.7
C3—C2—C1	113.3 (4)	C13—C14—H14A	105.7
C3—C2—H2B	108.9	C8—C14—H14A	105.7
C1—C2—H2B	108.9	C16—C15—C20	124.5 (5)
C3—C2—H2C	108.9	C16—C15—C12	112.6 (5)
C1—C2—H2C	108.9	C20—C15—C12	122.8 (4)
H2B—C2—H2C	107.7	C15—C16—C8	116.5 (5)
C24—O3—H3A	109.5	C15—C16—H16A	121.7
C4—C3—C2	110.2 (4)	C8—C16—H16A	121.7
C4—C3—H3B	109.6	C1—C17—H17A	109.5
C2—C3—H3B	109.6	C1—C17—H17B	109.5
C4—C3—H3C	109.6	H17A—C17—H17B	109.5
C2—C3—H3C	109.6	C1—C17—H17C	109.5
H3B—C3—H3C	108.1	H17A—C17—H17C	109.5
C3—C4—C5	113.7 (4)	H17B—C17—H17C	109.5
C3—C4—H4A	108.8	O1—C18—C1	114.7 (4)
C5—C4—H4A	108.8	O1—C18—H18A	108.6
C3—C4—H4B	108.8	C1—C18—H18A	108.6
C5—C4—H4B	108.8	O1—C18—H18B	108.6
H4A—C4—H4B	107.7	C1—C18—H18B	108.6
C4—C5—C7	107.9 (4)	H18A—C18—H18B	107.6
C4—C5—C6	108.9 (4)	C5—C19—H19A	109.5
C7—C5—C6	106.3 (3)	C5—C19—H19B	109.5
C4—C5—C19	109.7 (4)	H19A—C19—H19B	109.5
C7—C5—C19	111.3 (4)	C5—C19—H19C	109.5
C6—C5—C19	112.5 (4)	H19A—C19—H19C	109.5
C10—C6—C1	115.2 (4)	H19B—C19—H19C	109.5
C10—C6—C5	109.9 (4)	C15—C20—C22	113.7 (5)
C1—C6—C5	117.2 (4)	C15—C20—C21	108.9 (5)
C10—C6—H6A	104.3	C22—C20—C21	112.1 (6)
C1—C6—H6A	104.3	C15—C20—H20A	107.2
C5—C6—H6A	104.3	C22—C20—H20A	107.2
C5—C7—C8	116.9 (4)	C21—C20—H20A	107.2
C5—C7—C11	113.9 (4)	C20—C21—H21A	109.5
C8—C7—C11	108.5 (4)	C20—C21—H21B	109.5
C5—C7—H7A	105.5	H21A—C21—H21B	109.5
C8—C7—H7A	105.5	C20—C21—H21C	109.5
C11—C7—H7A	105.5	H21A—C21—H21C	109.5
C16—C8—C9	113.0 (4)	H21B—C21—H21C	109.5
C16—C8—C7	109.9 (3)	C20—C22—H22A	109.5
C9—C8—C7	111.1 (4)	C20—C22—H22B	109.5
C16—C8—C14	106.5 (3)	H22A—C22—H22B	109.5
C9—C8—C14	110.8 (4)	C20—C22—H22C	109.5
C7—C8—C14	105.1 (3)	H22A—C22—H22C	109.5
C10—C9—C8	114.3 (4)	H22B—C22—H22C	109.5
C10—C9—H9A	108.7	O2—C23—C13	108.5 (4)
C8—C9—H9A	108.7	O2—C23—H23A	110.0
C10—C9—H9B	108.7	C13—C23—H23A	110.0
C8—C9—H9B	108.7	O2—C23—H23B	110.0
H9A—C9—H9B	107.6	C13—C23—H23B	110.0
C9—C10—C6	111.1 (4)	H23A—C23—H23B	108.4
C9—C10—H10A	109.4	O3—C24—C14	111.5 (4)
C6—C10—H10A	109.4	O3—C24—H24A	109.3
C9—C10—H10B	109.4	C14—C24—H24A	109.3
C6—C10—H10B	109.4	O3—C24—H24B	109.3
H10A—C10—H10B	108.0	C14—C24—H24B	109.3
C12—C11—C7	109.9 (4)	H24A—C24—H24B	108.0
C12—C11—H11A	109.7	C25—O4—H4C	108.0
C7—C11—H11A	109.7	O4—C25—C26	125.2 (11)
C12—C11—H11B	109.7	O4—C25—H25A	106.0
C7—C11—H11B	109.7	C26—C25—H25A	106.0
H11A—C11—H11B	108.2	O4—C25—H25B	106.0
C15—C12—C11	108.2 (4)	C26—C25—H25B	106.0
C15—C12—C13	109.9 (4)	H25A—C25—H25B	106.3
C11—C12—C13	107.5 (4)	C25—C26—H26A	109.5
C15—C12—H12A	110.4	C25—C26—H26B	109.5
C11—C12—H12A	110.4	H26A—C26—H26B	109.5
C13—C12—H12A	110.4	C25—C26—H26C	109.5
C23—C13—C12	111.1 (4)	H26A—C26—H26C	109.5
C23—C13—C14	115.1 (4)	H26B—C26—H26C	109.5

C17—C1—C2—C3	75.7 (5)	C5—C7—C11—C12	137.0 (4)
C18—C1—C2—C3	−170.6 (4)	C8—C7—C11—C12	4.9 (5)
C6—C1—C2—C3	−50.7 (6)	C7—C11—C12—C15	−58.8 (5)
C1—C2—C3—C4	57.0 (6)	C7—C11—C12—C13	59.9 (5)
C2—C3—C4—C5	−58.6 (6)	C15—C12—C13—C23	−73.2 (5)
C3—C4—C5—C7	168.2 (4)	C11—C12—C13—C23	169.3 (4)
C3—C4—C5—C6	53.2 (5)	C15—C12—C13—C14	54.4 (5)
C3—C4—C5—C19	−70.3 (5)	C11—C12—C13—C14	−63.2 (5)
C17—C1—C6—C10	55.4 (5)	C23—C13—C14—C24	−3.2 (6)
C18—C1—C6—C10	−62.6 (5)	C12—C13—C14—C24	−128.5 (4)
C2—C1—C6—C10	179.5 (4)	C23—C13—C14—C8	127.1 (4)
C17—C1—C6—C5	−76.2 (6)	C12—C13—C14—C8	1.8 (5)
C18—C1—C6—C5	165.8 (4)	C16—C8—C14—C24	75.8 (5)
C2—C1—C6—C5	47.9 (5)	C9—C8—C14—C24	−47.4 (5)
C4—C5—C6—C10	177.1 (4)	C7—C8—C14—C24	−167.5 (4)
C7—C5—C6—C10	61.1 (5)	C16—C8—C14—C13	−55.2 (5)
C19—C5—C6—C10	−61.0 (5)	C9—C8—C14—C13	−178.4 (4)
C4—C5—C6—C1	−48.9 (5)	C7—C8—C14—C13	61.5 (4)
C7—C5—C6—C1	−165.0 (4)	C11—C12—C15—C16	59.2 (6)
C19—C5—C6—C1	72.9 (5)	C13—C12—C15—C16	−57.9 (5)
C4—C5—C7—C8	−170.1 (4)	C11—C12—C15—C20	−118.2 (5)
C6—C5—C7—C8	−53.3 (5)	C13—C12—C15—C20	124.7 (5)
C19—C5—C7—C8	69.6 (5)	C20—C15—C16—C8	176.0 (4)
C4—C5—C7—C11	62.0 (5)	C12—C15—C16—C8	−1.3 (6)
C6—C5—C7—C11	178.8 (4)	C9—C8—C16—C15	−179.8 (4)
C19—C5—C7—C11	−58.3 (5)	C7—C8—C16—C15	−55.0 (5)
C5—C7—C8—C16	−81.2 (5)	C14—C8—C16—C15	58.4 (5)
C11—C7—C8—C16	49.2 (5)	C17—C1—C18—O1	−178.4 (4)
C5—C7—C8—C9	44.7 (5)	C2—C1—C18—O1	64.3 (5)
C11—C7—C8—C9	175.1 (4)	C6—C1—C18—O1	−54.8 (6)
C5—C7—C8—C14	164.5 (4)	C16—C15—C20—C22	115.7 (7)
C11—C7—C8—C14	−65.0 (4)	C12—C15—C20—C22	−67.2 (8)
C16—C8—C9—C10	81.0 (5)	C16—C15—C20—C21	−118.4 (6)
C7—C8—C9—C10	−43.1 (6)	C12—C15—C20—C21	58.7 (6)
C14—C8—C9—C10	−159.6 (4)	C12—C13—C23—O2	−62.5 (5)
C8—C9—C10—C6	54.2 (6)	C14—C13—C23—O2	173.5 (4)
C1—C6—C10—C9	161.3 (4)	C13—C14—C24—O3	−71.8 (5)
C5—C6—C10—C9	−63.8 (5)	C8—C14—C24—O3	160.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4ⁱ	0.85	2.41	2.689 (6)	100
O2—H2A···O3ⁱⁱ	0.85	2.27	2.749 (5)	116
O3—H3A···O1ⁱⁱ	0.82	1.97	2.758 (5)	160
O4—H4C···O2ⁱⁱⁱ	0.85	1.90	2.704 (6)	157
C2—H2B···O1	0.97	2.57	2.979 (6)	106
C6—H6A···O1	0.98	2.50	2.959 (6)	108
C12—H12A···O2	0.98	2.54	2.918 (6)	103
C23—H23B···O3	0.97	2.43	3.086 (6)	124

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

Experimental details

Crystal data
Chemical formula	C₂₄H₄₀O₃·C₂H₆O
M_r	422.63
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.1440 (18), 9.6570 (19), 28.073 (6)
V (Å³)	2478.9 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 four-circle diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.978, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	4919, 2615, 1786
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.180, 1.00
No. of reflections	2615
No. of parameters	271
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.85	2.27	2.749 (5)	116
O3—H3A···O1ⁱ	0.82	1.97	2.758 (5)	160
O4—H4C···O2ⁱⁱ	0.85	1.90	2.704 (6)	157

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

Acknowledgements

We thank the Forestry Commonwealth Industry Special Foundation of China for support (No. 200704008).

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Halbrook, N. J. & Lawrence, R. V. (1958). J. Am. Chem. Soc. 80, 368–370. CrossRef CAS Web of Science Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Rao, X. P., Song, Z. Q., Yao, Y. J., Han, C. R. & Shang, S. B. (2008). Nat. Prod. Res. 22, 854–859. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1076

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

16-Iso­propyl-5,9-di­methyl­tetra­cyclo­[10.2.2.01,10.04,9]hexa­dec-15-ene-5,13,14-tri­methanol ethanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.0^1,10.0^4,9]hexadec-15-ene-5,13,14-trimethanol ethanol monosolvate