16-Isopropyl-5,9-dimethyl­tetra­cyclo­[10.2.2.01,10.04,9]hexa­dec-15-ene-5,13,14-tricarboxylic acid dimethyl­formamide disolvate

Xu, X.; Song, Z.; Wang, H.; Shang, S.

doi:10.1107/S1600536810016594

Volume 66
Part 6
Page o1318
June 2010

Received 17 March 2010
Accepted 6 May 2010
Online 12 May 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R = 0.066
wR = 0.182
Data-to-parameter ratio = 9.5
Details

16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.0^1,10.0^4,9]hexadec-15-ene-5,13,14-tricarboxylic acid dimethylformamide disolvate

Xu Xu,^a Zhan-qian Song,^a ^* Hong-xiao Wang ^a and Shi-bin Shang ^a

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

The title compound, C₂₄H₃₄O₆·2C₃H₇NO, which was isolated from fumaric-modified rosin, has four asymmetrically fused six-membered rings and three carboxylic acid substituents. It contains two fused and unbridged cyclohexane rings, which form a trans ring junction with a chair conformation. The asymmetric unit includes one fumaropimaric acid and two dimethylformamide molecules. The crystal structure is stabilized through intermolecular O-HO hydrogen bonds between dimethylformamide and fumaropimaric acid.

Related literature

For various applications of rosin, see: Halbrook & Lawrence (1958). For the separation of the title compound, see: Aldrich (1971); Halbrook & Lawrence (1959); Song et al. (2009).

Experimental

Crystal data

C₂₄H₃₄O₆·2C₃H₇NO
M_r = 564.70
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.1260 (14) Å
b = 11.342 (2) Å
c = 39.610 (8) Å
V = 3201.4 (11) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.975, T_max = 0.992
5821 measured reflections
3355 independent reflections
2039 reflections with I > 2(I)
R_int = 0.056
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.182
S = 0.99
3355 reflections
355 parameters
1 restraint
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO7ⁱ	0.82	1.85	2.653 (8)	168
O4-H4BO8ⁱⁱ	0.82	1.74	2.549 (6)	168
O5-H5AO3ⁱⁱⁱ	0.82	1.96	2.781 (5)	176
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) x+1, y, z; (iii) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2203 ).

Acknowledgements

This work was supported by the `948' program granted by the State Forestry Administration under grant No. 2006-4-C03.

References

Aldrich, P. H. (1971). US Patent No. 3 562 243.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Halbrook, N. J. & Lawrence, R. V. (1958). J. Am. Chem. Soc. 80, 368-370.
Halbrook, N. J. & Lawrence, R. V. (1959). US Patent No. 2 889 362.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, Z. Q., Xu, X., Shang, S. B., Wang, H. X. & Rao, X. P (2009). Chinese Patent CN 101591239.

organic compounds

16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadec-15-ene-5,13,14-tricarboxylic acid dimethylformamide disolvate