7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodeca­hydro­phenan­threne-1-carboxylic acid

Rao, X.-P.; Song, Z.-Q.; Shang, S.-B.; Wu, Y.

doi:10.1107/S1600536809042305

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2804

https://doi.org/10.1107/S1600536809042305

Open

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7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

Xiao-Ping Rao,^a ^* Zhan-Qian Song,^a Shi-Bin Shang ^a and Yong Wu ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
^*Correspondence e-mail: rxping2001@163.com

(Received 29 September 2009; accepted 15 October 2009; online 23 October 2009)

The title compound, C₂₀H₃₂O₂, has been isolated from hydrogenated rosin. There are two independent molecules in the asymmetric unit. In each molecule, the cyclohexane ring assumes a chair conformation, while the two cyclohexene rings adopt half-chair and envelope conformations. Intermolecular O—H⋯O hydrogen bonding between carboxyl groups links pairs of independent molecules into dimers.

Related literature

For the applications of pine resin acids, see: Piispanen et al. (2001 ); Jia et al. (2009 ); Sepulveda et al. (2005 ); Rao, Song & He (2008 ); Rao, Song, He & Jia (2008 ); Bicu & Mustata (2000 ); Hoa et al. (1993 ).

Experimental

Crystal data

C₂₀H₃₂O₂
M_r = 304.42
Monoclinic, P 2₁
a = 11.543 (2) Å
b = 13.580 (3) Å
c = 13.345 (3) Å
β = 114.93 (3)°
V = 1897.0 (7) 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 diffractometer
Absorption correction: none
3775 measured reflections
3590 independent reflections
2046 reflections with I > 2σ(I)
R_int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.194
S = 1.00
3590 reflections
385 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2D⋯O3ⁱ	0.82	1.82	2.632 (6)	170
O4—H4B⋯O1ⁱⁱ	0.82	1.82	2.638 (6)	173
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+2]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809042305/xu2627sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042305/xu2627Isup2.hkl

checkCIF report

Comment top

Pine resin acids are natural diterpenoid compounds, monocarboxylic acids of alkylated hydrophenanthrene acids constitutes the principal resin acid. Pine resin acids are widely used as starting material for design and synthesis of surfactants (Piispanen et al., 2001; Jia et al., 2009), biological compounds (Sepulveda et al., 2005; Rao et al., 2008a,b) and polymers (Bicu et al., 2000; Hoa et al., 1993). In this work we describe the crystal structure of the title compound.

Two crystallorgraphica independent molecules exist in the title structure, in each molecule there are three six-membered rings, in which they form half-chair, envelope and chair conformations, respectively (Fig. 1). The two methyl groups in the same side of tricyclo phenanthrene structure. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds (Table 1).

Related literature top

For the applications of pine resin acids, see: Piispanen et al. (2001); Jia et al. (2009); Sepulveda et al. (2005); Rao, Song & He (2008); Rao, Song, He & Jia (2008); Bicu & Mustata (2000); Hoa et al. (1993). A Alerts fixed (authors supplied correct fcf file)

Experimental top

The title compound was isolated from hydrogenated rosin by recrystallization 5 times from acetone. Single crystals were grown from acetone.

Structure description top

For the applications of pine resin acids, see: Piispanen et al. (2001); Jia et al. (2009); Sepulveda et al. (2005); Rao, Song & He (2008); Rao, Song, He & Jia (2008); Bicu & Mustata (2000); Hoa et al. (1993). A Alerts fixed (authors supplied correct fcf file)

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with atom labels. Displacement ellipsoids were drawn at the 30% probability level.

7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a- dodecahydrophenanthrene-1-carboxylic acid top

Crystal data top

C₂₀H₃₂O₂	F(000) = 672
M_r = 304.42	D_x = 1.066 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 11.543 (2) Å	θ = 10–13°
b = 13.580 (3) Å	µ = 0.07 mm⁻¹
c = 13.345 (3) Å	T = 293 K
β = 114.93 (3)°	Block, colorless
V = 1897.0 (7) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.025
Radiation source: fine-focus sealed tube	θ_max = 25.3°, θ_min = 1.7°
Graphite monochromator	h = 0→13
ω/2θ scans	k = 0→16
3775 measured reflections	l = −16→14
3590 independent reflections	3 standard reflections every 200 reflections
2046 reflections with I > 2σ(I)	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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.113P)²] where P = (F_o² + 2F_c²)/3
3590 reflections	(Δ/σ)_max = 0.002
385 parameters	Δρ_max = 0.41 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₃₂O₂	V = 1897.0 (7) Å³
M_r = 304.42	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.543 (2) Å	µ = 0.07 mm⁻¹
b = 13.580 (3) Å	T = 293 K
c = 13.345 (3) Å	0.30 × 0.20 × 0.10 mm
β = 114.93 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.025
3775 measured reflections	3 standard reflections every 200 reflections
3590 independent reflections	intensity decay: 1%
2046 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.194	H-atom parameters constrained
S = 1.00	Δρ_max = 0.41 e Å⁻³
3590 reflections	Δρ_min = −0.18 e Å⁻³
385 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	0.5995 (3)	−0.3368 (3)	0.9250 (4)	0.0953 (14)
O2	0.7106 (3)	−0.2421 (4)	0.8667 (4)	0.1058 (16)
H2D	0.7689	−0.2728	0.9145	0.159*
C1	0.5526 (10)	0.4293 (8)	0.7003 (9)	0.162 (4)
H1A	0.5698	0.4958	0.7268	0.242*
H1B	0.4692	0.4258	0.6402	0.242*
H1C	0.6155	0.4087	0.6752	0.242*
C2	0.6790 (9)	0.3821 (7)	0.8947 (8)	0.151 (3)
H2A	0.6744	0.3412	0.9515	0.226*
H2B	0.6852	0.4499	0.9168	0.226*
H2C	0.7530	0.3645	0.8830	0.226*
C3	0.5574 (8)	0.3672 (6)	0.7861 (8)	0.117 (2)
H3A	0.4866	0.3885	0.8031	0.140*
C4	0.5336 (5)	0.2562 (5)	0.7585 (6)	0.0872 (17)
H4A	0.5989	0.2350	0.7342	0.105*
C5	0.4077 (6)	0.2351 (5)	0.6649 (6)	0.101 (2)
H5A	0.3967	0.2776	0.6030	0.122*
H5B	0.3399	0.2497	0.6873	0.122*
C6	0.3975 (5)	0.1284 (4)	0.6285 (5)	0.0835 (17)
H6A	0.3094	0.1146	0.5788	0.100*
H6B	0.4488	0.1192	0.5874	0.100*
C7	0.4403 (4)	0.0550 (4)	0.7227 (5)	0.0673 (14)
C8	0.5082 (5)	0.0867 (4)	0.8256 (5)	0.0743 (15)
C9	0.5507 (6)	0.1922 (5)	0.8566 (6)	0.0921 (19)
H9A	0.5022	0.2205	0.8938	0.111*
H9B	0.6401	0.1926	0.9083	0.111*
C10	0.4006 (4)	−0.0506 (4)	0.6951 (4)	0.0667 (14)
C11	0.4961 (4)	−0.1151 (4)	0.7890 (4)	0.0656 (14)
H11A	0.5800	−0.0982	0.7920	0.079*
C12	0.5025 (5)	−0.0827 (5)	0.9023 (5)	0.0780 (16)
H12A	0.4178	−0.0849	0.9009	0.094*
H12B	0.5573	−0.1271	0.9596	0.094*
C13	0.5550 (6)	0.0217 (5)	0.9272 (5)	0.0840 (17)
H13A	0.5302	0.0508	0.9815	0.101*
H13B	0.6476	0.0190	0.9590	0.101*
C14	0.4079 (5)	−0.0832 (4)	0.5888 (4)	0.0774 (16)
H14A	0.4900	−0.0634	0.5918	0.093*
H14B	0.3423	−0.0487	0.5274	0.093*
C15	0.3914 (6)	−0.1936 (5)	0.5660 (5)	0.0931 (19)
H15A	0.3066	−0.2135	0.5565	0.112*
H15B	0.3994	−0.2082	0.4981	0.112*
C16	0.4894 (6)	−0.2508 (5)	0.6590 (5)	0.0857 (17)
H16A	0.5736	−0.2339	0.6648	0.103*
H16B	0.4761	−0.3206	0.6424	0.103*
C17	0.4845 (5)	−0.2311 (4)	0.7703 (5)	0.0758 (16)
C18	0.2594 (4)	−0.0591 (6)	0.6788 (5)	0.097 (2)
H18A	0.2306	−0.1257	0.6600	0.145*
H18B	0.2069	−0.0159	0.6203	0.145*
H18C	0.2535	−0.0409	0.7460	0.145*
C19	0.3683 (5)	−0.2784 (5)	0.7804 (6)	0.113 (2)
H19A	0.3678	−0.3480	0.7674	0.169*
H19B	0.2911	−0.2496	0.7268	0.169*
H19C	0.3737	−0.2671	0.8533	0.169*
C20	0.6034 (5)	−0.2739 (4)	0.8604 (5)	0.0715 (14)
O3	1.0841 (3)	0.1724 (4)	0.9849 (3)	0.0991 (14)
O4	1.1955 (3)	0.0884 (4)	0.9141 (3)	0.1037 (15)
H4B	1.2551	0.1139	0.9661	0.156*
C21	1.0284 (11)	−0.0278 (10)	0.1895 (9)	0.164 (2)
H21A	1.0483	−0.0113	0.1286	0.246*
H21B	0.9479	−0.0616	0.1625	0.246*
H21C	1.0941	−0.0696	0.2400	0.246*
C22	1.1466 (10)	0.0976 (10)	0.2801 (8)	0.164 (2)
H22A	1.1628	0.1577	0.3218	0.246*
H22B	1.1602	0.1082	0.2147	0.246*
H22C	1.2035	0.0472	0.3243	0.246*
C23	1.0201 (11)	0.0682 (10)	0.2501 (9)	0.164 (2)
H23A	0.9582	0.1153	0.2004	0.197*
C24	0.9939 (7)	0.0429 (7)	0.3525 (5)	0.110 (3)
H24A	1.0632	0.0000	0.4007	0.132*
C25	0.8671 (7)	−0.0108 (6)	0.3270 (5)	0.110 (3)
H25A	0.7960	0.0328	0.2866	0.132*
H25B	0.8601	−0.0680	0.2813	0.132*
C26	0.8618 (6)	−0.0429 (5)	0.4348 (5)	0.0893 (18)
H26A	0.7753	−0.0631	0.4191	0.107*
H26B	0.9171	−0.0996	0.4639	0.107*
C27	0.9020 (5)	0.0367 (4)	0.5217 (4)	0.0645 (13)
C28	0.9620 (5)	0.1162 (4)	0.5122 (4)	0.0692 (14)
C29	0.9967 (6)	0.1337 (6)	0.4162 (5)	0.0893 (19)
H29A	0.9377	0.1813	0.3666	0.107*
H29B	1.0817	0.1619	0.4442	0.107*
C30	0.8702 (4)	0.0187 (4)	0.6208 (4)	0.0581 (12)
C31	0.9664 (4)	0.0813 (4)	0.7182 (4)	0.0609 (13)
H31A	1.0507	0.0599	0.7255	0.073*
C32	0.9591 (5)	0.1894 (4)	0.6862 (5)	0.0763 (16)
H32A	0.8724	0.2133	0.6626	0.092*
H32B	1.0145	0.2281	0.7494	0.092*
C33	1.0000 (5)	0.2002 (4)	0.5941 (5)	0.0804 (16)
H33A	1.0923	0.2068	0.6259	0.097*
H33B	0.9639	0.2606	0.5545	0.097*
C34	0.8919 (6)	−0.0900 (4)	0.6569 (5)	0.0815 (16)
H34A	0.8284	−0.1304	0.6004	0.098*
H34B	0.9755	−0.1105	0.6637	0.098*
C35	0.8836 (6)	−0.1070 (5)	0.7676 (5)	0.096 (2)
H35A	0.7988	−0.0894	0.7599	0.115*
H35B	0.8969	−0.1763	0.7867	0.115*
C36	0.9802 (6)	−0.0478 (5)	0.8582 (5)	0.0916 (19)
H36A	1.0648	−0.0696	0.8696	0.110*
H36B	0.9707	−0.0602	0.9259	0.110*
C37	0.9695 (5)	0.0636 (5)	0.8356 (4)	0.0731 (16)
C38	0.7292 (4)	0.0467 (5)	0.5848 (5)	0.0867 (17)
H38A	0.6762	0.0052	0.5248	0.130*
H38B	0.7166	0.1143	0.5613	0.130*
H38C	0.7068	0.0383	0.6459	0.130*
C39	0.8541 (5)	0.1048 (6)	0.8505 (5)	0.101 (2)
H39A	0.8626	0.0900	0.9236	0.152*
H39B	0.7773	0.0753	0.7971	0.152*
H39C	0.8502	0.1748	0.8400	0.152*
C40	1.0881 (4)	0.1130 (5)	0.9177 (4)	0.0701 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.063 (2)	0.101 (3)	0.111 (3)	−0.009 (2)	0.026 (2)	0.039 (3)
O2	0.054 (2)	0.123 (4)	0.131 (3)	0.006 (2)	0.031 (2)	0.061 (3)
C1	0.158 (8)	0.104 (7)	0.171 (9)	−0.017 (6)	0.019 (7)	0.025 (7)
C2	0.145 (7)	0.095 (6)	0.184 (9)	−0.013 (6)	0.041 (7)	−0.028 (6)
C3	0.110 (5)	0.073 (5)	0.153 (7)	0.002 (4)	0.041 (5)	−0.014 (5)
C4	0.071 (3)	0.083 (5)	0.104 (4)	0.005 (3)	0.033 (3)	−0.004 (4)
C5	0.085 (4)	0.077 (5)	0.120 (5)	0.017 (3)	0.022 (4)	0.013 (4)
C6	0.064 (3)	0.073 (4)	0.089 (4)	0.005 (3)	0.008 (3)	0.009 (3)
C7	0.047 (2)	0.072 (4)	0.081 (4)	0.013 (2)	0.025 (3)	0.008 (3)
C8	0.069 (3)	0.071 (4)	0.079 (4)	0.015 (3)	0.027 (3)	0.003 (3)
C9	0.090 (4)	0.083 (4)	0.111 (5)	0.001 (3)	0.050 (4)	−0.029 (4)
C10	0.045 (2)	0.077 (4)	0.075 (3)	0.005 (3)	0.022 (2)	0.001 (3)
C11	0.047 (2)	0.078 (4)	0.068 (3)	0.000 (3)	0.022 (2)	0.014 (3)
C12	0.071 (3)	0.091 (4)	0.080 (4)	0.011 (3)	0.039 (3)	0.011 (3)
C13	0.092 (4)	0.091 (5)	0.075 (4)	0.007 (3)	0.042 (3)	−0.007 (3)
C14	0.072 (3)	0.069 (4)	0.069 (3)	−0.002 (3)	0.008 (3)	−0.005 (3)
C15	0.085 (4)	0.083 (5)	0.082 (4)	−0.008 (3)	0.007 (3)	−0.005 (4)
C16	0.100 (4)	0.062 (4)	0.074 (4)	−0.002 (3)	0.016 (3)	−0.003 (3)
C17	0.051 (3)	0.070 (4)	0.098 (4)	−0.012 (3)	0.023 (3)	0.006 (3)
C18	0.042 (3)	0.117 (5)	0.120 (5)	0.009 (3)	0.023 (3)	0.020 (4)
C19	0.063 (3)	0.100 (5)	0.146 (6)	−0.028 (3)	0.015 (4)	0.027 (5)
C20	0.060 (3)	0.072 (4)	0.083 (4)	−0.005 (3)	0.030 (3)	0.015 (3)
O3	0.072 (2)	0.134 (4)	0.094 (3)	−0.010 (2)	0.038 (2)	−0.040 (3)
O4	0.054 (2)	0.156 (4)	0.092 (3)	0.003 (2)	0.0222 (18)	−0.032 (3)
C21	0.170 (5)	0.192 (6)	0.159 (5)	0.045 (5)	0.098 (5)	0.032 (5)
C22	0.170 (5)	0.192 (6)	0.159 (5)	0.045 (5)	0.098 (5)	0.032 (5)
C23	0.170 (5)	0.192 (6)	0.159 (5)	0.045 (5)	0.098 (5)	0.032 (5)
C24	0.107 (5)	0.158 (8)	0.075 (4)	0.057 (5)	0.048 (4)	0.035 (5)
C25	0.118 (6)	0.131 (6)	0.064 (4)	0.035 (5)	0.022 (4)	−0.020 (4)
C26	0.087 (4)	0.092 (4)	0.087 (4)	−0.009 (3)	0.034 (3)	−0.025 (4)
C27	0.055 (3)	0.065 (3)	0.067 (3)	0.008 (3)	0.020 (2)	−0.004 (3)
C28	0.060 (3)	0.082 (4)	0.070 (3)	0.004 (3)	0.032 (2)	0.021 (3)
C29	0.083 (4)	0.114 (5)	0.075 (4)	0.013 (4)	0.037 (3)	0.032 (4)
C30	0.052 (2)	0.051 (3)	0.070 (3)	−0.007 (2)	0.025 (2)	0.000 (2)
C31	0.042 (2)	0.076 (4)	0.067 (3)	0.000 (2)	0.025 (2)	0.003 (3)
C32	0.064 (3)	0.055 (3)	0.093 (4)	−0.005 (3)	0.017 (3)	−0.004 (3)
C33	0.065 (3)	0.074 (4)	0.090 (4)	−0.008 (3)	0.020 (3)	0.006 (3)
C34	0.081 (4)	0.066 (4)	0.096 (4)	−0.026 (3)	0.035 (3)	−0.001 (3)
C35	0.099 (4)	0.079 (5)	0.111 (5)	−0.018 (4)	0.045 (4)	0.014 (4)
C36	0.093 (4)	0.097 (5)	0.089 (4)	−0.008 (4)	0.043 (4)	0.021 (4)
C37	0.061 (3)	0.090 (5)	0.073 (3)	−0.004 (3)	0.034 (3)	−0.005 (3)
C38	0.054 (3)	0.107 (5)	0.091 (4)	−0.013 (3)	0.022 (3)	−0.022 (4)
C39	0.054 (3)	0.154 (7)	0.102 (4)	0.001 (4)	0.039 (3)	−0.022 (4)
C40	0.059 (3)	0.092 (4)	0.061 (3)	−0.004 (3)	0.027 (2)	−0.008 (3)

Geometric parameters (Å, º) top

O1—C20	1.228 (6)	O3—C40	1.221 (6)
O2—C20	1.280 (6)	O4—C40	1.304 (6)
O2—H2D	0.8200	O4—H4B	0.8200
C1—C3	1.404 (12)	C21—C23	1.559 (16)
C1—H1A	0.9600	C21—H21A	0.9600
C1—H1B	0.9600	C21—H21B	0.9600
C1—H1C	0.9600	C21—H21C	0.9600
C2—C3	1.548 (11)	C22—C23	1.400 (14)
C2—H2A	0.9600	C22—H22A	0.9600
C2—H2B	0.9600	C22—H22B	0.9600
C2—H2C	0.9600	C22—H22C	0.9600
C3—C4	1.549 (10)	C23—C24	1.557 (11)
C3—H3A	0.9800	C23—H23A	0.9800
C4—C5	1.491 (9)	C24—C29	1.490 (11)
C4—C9	1.513 (9)	C24—C25	1.539 (11)
C4—H4A	0.9800	C24—H24A	0.9800
C5—C6	1.517 (9)	C25—C26	1.529 (9)
C5—H5A	0.9700	C25—H25A	0.9700
C5—H5B	0.9700	C25—H25B	0.9700
C6—C7	1.515 (8)	C26—C27	1.508 (8)
C6—H6A	0.9700	C26—H26A	0.9700
C6—H6B	0.9700	C26—H26B	0.9700
C7—C8	1.333 (7)	C27—C28	1.317 (7)
C7—C10	1.504 (8)	C27—C30	1.534 (7)
C8—C13	1.514 (8)	C28—C33	1.511 (8)
C8—C9	1.515 (9)	C28—C29	1.513 (7)
C9—H9A	0.9700	C29—H29A	0.9700
C9—H9B	0.9700	C29—H29B	0.9700
C10—C14	1.521 (8)	C30—C38	1.539 (7)
C10—C11	1.545 (7)	C30—C34	1.539 (8)
C10—C18	1.556 (7)	C30—C31	1.558 (7)
C11—C12	1.547 (8)	C31—C32	1.521 (8)
C11—C17	1.591 (8)	C31—C37	1.571 (7)
C11—H11A	0.9800	C31—H31A	0.9800
C12—C13	1.522 (9)	C32—C33	1.499 (8)
C12—H12A	0.9700	C32—H32A	0.9700
C12—H12B	0.9700	C32—H32B	0.9700
C13—H13A	0.9700	C33—H33A	0.9700
C13—H13B	0.9700	C33—H33B	0.9700
C14—C15	1.527 (9)	C34—C35	1.539 (9)
C14—H14A	0.9700	C34—H34A	0.9700
C14—H14B	0.9700	C34—H34B	0.9700
C15—C16	1.496 (8)	C35—C36	1.488 (9)
C15—H15A	0.9700	C35—H35A	0.9700
C15—H15B	0.9700	C35—H35B	0.9700
C16—C17	1.534 (8)	C36—C37	1.538 (9)
C16—H16A	0.9700	C36—H36A	0.9700
C16—H16B	0.9700	C36—H36B	0.9700
C17—C20	1.508 (8)	C37—C40	1.503 (7)
C17—C19	1.544 (8)	C37—C39	1.532 (7)
C18—H18A	0.9600	C38—H38A	0.9600
C18—H18B	0.9600	C38—H38B	0.9600
C18—H18C	0.9600	C38—H38C	0.9600
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600

C20—O2—H2D	109.5	C40—O4—H4B	109.5
C3—C1—H1A	109.5	C23—C21—H21A	109.5
C3—C1—H1B	109.5	C23—C21—H21B	109.5
H1A—C1—H1B	109.5	H21A—C21—H21B	109.5
C3—C1—H1C	109.5	C23—C21—H21C	109.5
H1A—C1—H1C	109.5	H21A—C21—H21C	109.5
H1B—C1—H1C	109.5	H21B—C21—H21C	109.5
C3—C2—H2A	109.5	C23—C22—H22A	109.5
C3—C2—H2B	109.5	C23—C22—H22B	109.5
H2A—C2—H2B	109.5	H22A—C22—H22B	109.5
C3—C2—H2C	109.5	C23—C22—H22C	109.5
H2A—C2—H2C	109.5	H22A—C22—H22C	109.5
H2B—C2—H2C	109.5	H22B—C22—H22C	109.5
C1—C3—C2	113.2 (8)	C22—C23—C24	112.2 (9)
C1—C3—C4	116.6 (8)	C22—C23—C21	95.9 (9)
C2—C3—C4	110.5 (7)	C24—C23—C21	110.4 (9)
C1—C3—H3A	105.1	C22—C23—H23A	112.5
C2—C3—H3A	105.1	C24—C23—H23A	112.5
C4—C3—H3A	105.1	C21—C23—H23A	112.5
C5—C4—C9	109.9 (6)	C29—C24—C25	107.9 (5)
C5—C4—C3	113.5 (6)	C29—C24—C23	110.7 (8)
C9—C4—C3	114.0 (6)	C25—C24—C23	115.4 (7)
C5—C4—H4A	106.3	C29—C24—H24A	107.5
C9—C4—H4A	106.3	C25—C24—H24A	107.5
C3—C4—H4A	106.3	C23—C24—H24A	107.5
C4—C5—C6	111.6 (5)	C26—C25—C24	109.8 (5)
C4—C5—H5A	109.3	C26—C25—H25A	109.7
C6—C5—H5A	109.3	C24—C25—H25A	109.7
C4—C5—H5B	109.3	C26—C25—H25B	109.7
C6—C5—H5B	109.3	C24—C25—H25B	109.7
H5A—C5—H5B	108.0	H25A—C25—H25B	108.2
C7—C6—C5	114.1 (5)	C27—C26—C25	113.5 (6)
C7—C6—H6A	108.7	C27—C26—H26A	108.9
C5—C6—H6A	108.7	C25—C26—H26A	108.9
C7—C6—H6B	108.7	C27—C26—H26B	108.9
C5—C6—H6B	108.7	C25—C26—H26B	108.9
H6A—C6—H6B	107.6	H26A—C26—H26B	107.7
C8—C7—C10	123.1 (5)	C28—C27—C26	121.1 (5)
C8—C7—C6	119.2 (5)	C28—C27—C30	122.7 (5)
C10—C7—C6	117.7 (5)	C26—C27—C30	116.2 (5)
C7—C8—C13	124.5 (6)	C27—C28—C33	123.5 (5)
C7—C8—C9	124.7 (6)	C27—C28—C29	123.2 (6)
C13—C8—C9	110.8 (5)	C33—C28—C29	113.2 (5)
C4—C9—C8	113.4 (5)	C24—C29—C28	113.8 (6)
C4—C9—H9A	108.9	C24—C29—H29A	108.8
C8—C9—H9A	108.9	C28—C29—H29A	108.8
C4—C9—H9B	108.9	C24—C29—H29B	108.8
C8—C9—H9B	108.9	C28—C29—H29B	108.8
H9A—C9—H9B	107.7	H29A—C29—H29B	107.7
C7—C10—C14	112.0 (5)	C27—C30—C38	107.3 (4)
C7—C10—C11	107.6 (4)	C27—C30—C34	110.8 (4)
C14—C10—C11	106.9 (4)	C38—C30—C34	110.3 (4)
C7—C10—C18	107.3 (5)	C27—C30—C31	106.6 (4)
C14—C10—C18	108.3 (5)	C38—C30—C31	114.4 (4)
C11—C10—C18	114.7 (5)	C34—C30—C31	107.3 (4)
C10—C11—C12	110.8 (4)	C32—C31—C30	111.0 (4)
C10—C11—C17	116.8 (4)	C32—C31—C37	113.7 (4)
C12—C11—C17	113.7 (5)	C30—C31—C37	117.2 (4)
C10—C11—H11A	104.8	C32—C31—H31A	104.5
C12—C11—H11A	104.8	C30—C31—H31A	104.5
C17—C11—H11A	104.8	C37—C31—H31A	104.5
C13—C12—C11	109.2 (5)	C33—C32—C31	108.9 (5)
C13—C12—H12A	109.8	C33—C32—H32A	109.9
C11—C12—H12A	109.8	C31—C32—H32A	109.9
C13—C12—H12B	109.8	C33—C32—H32B	109.9
C11—C12—H12B	109.8	C31—C32—H32B	109.9
H12A—C12—H12B	108.3	H32A—C32—H32B	108.3
C8—C13—C12	112.9 (5)	C32—C33—C28	115.1 (4)
C8—C13—H13A	109.0	C32—C33—H33A	108.5
C12—C13—H13A	109.0	C28—C33—H33A	108.5
C8—C13—H13B	109.0	C32—C33—H33B	108.5
C12—C13—H13B	109.0	C28—C33—H33B	108.5
H13A—C13—H13B	107.8	H33A—C33—H33B	107.5
C10—C14—C15	114.8 (5)	C35—C34—C30	112.1 (5)
C10—C14—H14A	108.6	C35—C34—H34A	109.2
C15—C14—H14A	108.6	C30—C34—H34A	109.2
C10—C14—H14B	108.6	C35—C34—H34B	109.2
C15—C14—H14B	108.6	C30—C34—H34B	109.2
H14A—C14—H14B	107.5	H34A—C34—H34B	107.9
C16—C15—C14	111.0 (5)	C36—C35—C34	111.7 (5)
C16—C15—H15A	109.4	C36—C35—H35A	109.3
C14—C15—H15A	109.4	C34—C35—H35A	109.3
C16—C15—H15B	109.4	C36—C35—H35B	109.3
C14—C15—H15B	109.4	C34—C35—H35B	109.3
H15A—C15—H15B	108.0	H35A—C35—H35B	107.9
C15—C16—C17	112.9 (5)	C35—C36—C37	113.7 (5)
C15—C16—H16A	109.0	C35—C36—H36A	108.8
C17—C16—H16A	109.0	C37—C36—H36A	108.8
C15—C16—H16B	109.0	C35—C36—H36B	108.8
C17—C16—H16B	109.0	C37—C36—H36B	108.8
H16A—C16—H16B	107.8	H36A—C36—H36B	107.7
C20—C17—C16	108.2 (5)	C40—C37—C39	108.5 (5)
C20—C17—C19	107.6 (5)	C40—C37—C36	108.9 (5)
C16—C17—C19	113.5 (5)	C39—C37—C36	109.6 (5)
C20—C17—C11	105.6 (4)	C40—C37—C31	106.9 (4)
C16—C17—C11	106.8 (5)	C39—C37—C31	114.7 (5)
C19—C17—C11	114.7 (5)	C36—C37—C31	108.2 (5)
C10—C18—H18A	109.5	C30—C38—H38A	109.5
C10—C18—H18B	109.5	C30—C38—H38B	109.5
H18A—C18—H18B	109.5	H38A—C38—H38B	109.5
C10—C18—H18C	109.5	C30—C38—H38C	109.5
H18A—C18—H18C	109.5	H38A—C38—H38C	109.5
H18B—C18—H18C	109.5	H38B—C38—H38C	109.5
C17—C19—H19A	109.5	C37—C39—H39A	109.5
C17—C19—H19B	109.5	C37—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C17—C19—H19C	109.5	C37—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
O1—C20—O2	120.6 (5)	O3—C40—O4	121.8 (5)
O1—C20—C17	122.6 (5)	O3—C40—C37	121.7 (5)
O2—C20—C17	116.8 (5)	O4—C40—C37	116.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···O3ⁱ	0.82	1.82	2.632 (6)	170
O4—H4B···O1ⁱⁱ	0.82	1.82	2.638 (6)	173

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

Experimental details

Crystal data
Chemical formula	C₂₀H₃₂O₂
M_r	304.42
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.543 (2), 13.580 (3), 13.345 (3)
β (°)	114.93 (3)
V (Å³)	1897.0 (7)
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
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3775, 3590, 2046
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.194, 1.00
No. of reflections	3590
No. of parameters	385
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···O3ⁱ	0.82	1.82	2.632 (6)	170
O4—H4B···O1ⁱⁱ	0.82	1.82	2.638 (6)	173

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

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangsu Province (BK2008088) and the Fundamental Research Foundation of the Central Commonwealth Institute of the Chinese Academy of Forestry (CAFYBB2008021).

References

Bicu, I. & Mustata, F. (2000). Makromol. Mater. Eng. 280–281, 47–53. Web of Science CrossRef Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Hoa, L. T. N., Pascault, J. P., My, L. T. & Son, C. P. N. (1993). Eur. Polym. J. 29, 491–495. Google Scholar
Jia, W. H., Rao, X. P., Song, Z. Q. & Shang, S. B. (2009). J. Surf. Det. 12, 261–267. Web of Science CrossRef CAS Google Scholar
Piispanen, P. S., Hedman, B. & Norin, T. (2001). J. Surf. Det. 5, 165–168. Web of Science CrossRef Google Scholar
Rao, X.-P., Song, Z.-Q. & He, L. (2008). Heteroat. Chem. 19, 512–516. Web of Science CrossRef CAS Google Scholar
Rao, X.-P., Song, Z.-Q., He, L. & Jia, W.-H. (2008). Chem. Pharm. Bull. 56, 1575–1578. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sepulveda, B., Astudillo, L., Rodriguez, J., Yanez, T., Theoduloz, C. & Schmeda, G. (2005). Pharm. Res. 52, 429–437. Web of Science CrossRef 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

7-Iso­propyl-1,4a-di­methyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodeca­hydro­phenan­threne-1-carboxylic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid