5-(2,5-Dioxooxolan-3-yl)-8-methyl-3,3a,4,5-tetra­hydro-1H-naphtho­[1,2-c]furan-1,3-dione

Guo, Y.Z.; Liu, J.G.; Yang, S.Y.

doi:10.1107/S1600536813000482

Volume 69
Part 2
Page o226
February 2013

Received 27 December 2012
Accepted 6 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.113
Data-to-parameter ratio = 15.0
Details

5-(2,5-Dioxooxolan-3-yl)-8-methyl-3,3a,4,5-tetrahydro-1H-naphtho[1,2-c]furan-1,3-dione

Y. Z. Guo,^a J. G. Liu ^a ^* and S. Y. Yang ^a ^*

^aLaboratory of Advanced Polymer Materials, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), Beijing 100190, People's Republic of China
Correspondence e-mail: liujg@iccas.ac.cn, shiyang@iccas.ac.cn

In the title compound, C₁₇H₁₄O₆, the dihedral angle between the two anhydride rings is 76.01 (8)°while the dihedral angles between the benzene and anhydride rings are 42.60 (7) and 68.94 (7)°. The cyclohexene ring of the tetrahydronaphthalene unit exhibits an envelope conformation.

Related literature

For applications of tetralin-containing dianhydrides, see: Liaw et al. (2012); Matsumoto et al. (2009); Hasegawa & Horie (2001). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₁₄O₆
M_r = 314.28
Triclinic, $[P \overline 1]$
a = 6.6907 (13) Å
b = 9.166 (2) Å
c = 11.839 (2) Å
= 78.628 (8)°
= 78.352 (9)°
= 79.054 (9)°
V = 688.5 (2) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 173 K
0.28 × 0.22 × 0.12 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) T_min = 0.680, T_max = 1.000
8959 measured reflections
3137 independent reflections
2864 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.113
S = 1.07
3137 reflections
209 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.22 e Å^-3

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009); molecular graphics: OLEX2; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2186 ).

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support. They also thank Dr Tong Lin Liang of ICCAS for the X-ray data collection.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Hasegawa, M. & Horie, K. (2001). Prog. Polym. Sci. 26, 259-335.
Liaw, D. J., Wang, K. L., Huang, Y. C., Lee, K. R., Lai, J. Y. & Ha, C. S. (2012). Prog. Polym. Sci. 37, 907-974.
Matsumoto, T., Mikami, D., Hashimoto, T., Kaise, M., Takahashi, R. & Kawabata, S. (2009). J. Phys. Conf. Ser. 187, 012005.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds