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Volume 69 
Part 7 
Pages o1031-o1032  
July 2013  

Received 12 April 2013
Accepted 30 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.108
Data-to-parameter ratio = 14.9
Details
Open access

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

aLaboratory of Advanced Polymer Materials, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), Beijing 100190, People's Republic of China, and bBeijing BOE Display Technology Co., Ltd, No. 118 Jinghaiyilu, BDA, Beijing 100176
Correspondence e-mail: liujg@iccas.ac.cn

The title compound, C17H13ClO6, is an asymmetric alicyclic dianhydride containing a chloromethyl-substituted tetrahydronaphthalene moiety. The cyclohexene ring in the tetrahydronaphthalene moiety exhibits an envelope conformation with the tertiary C atom as the flap The dihedral angle between the two anhydride rings is 79.96 (6)°, while those between the benzene ring and the non-fused and fused anhydride rings are 71.03 (5) and 42.57 (7)°, respectively. In the crystal, molecules are connected by weak C-H...O interactions, forming a three-dimensional supramolecular structure.

Related literature

For background to polyimides, see: Li et al. (2005[Li, X. D., Zhong, Z. X., Han, S. H., Lee, S. H. & Lee, M. H. (2005). Polym. Int. 54, 406-411.]); Liaw et al. (2012[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.]); Zhang et al. (2003[Zhang, A. Q., Li, X. D., Nah, C. W., Hwang, K. J. & Lee, M. H. (2003). J. Polym. Sci. Part A Polym. Chem. 41, 22-29.]); Zhong et al. (2004[Zhong, Z. X., Li, X. D., Lee, S. H. & Lee, M. H. (2004). Mol. Cryst. Liq. Cryst. 425, 145-152.]). For background to and applications of tetrahydronaphthalene-containing alicyclic dianhydrides, see: Guo, Shen et al. (2013[Guo, Y. Z., Shen, D. X., Ni, H. J., Liu, J. G. & Yang, S. Y. (2013). Prog. Org. Coat. 76, 768-777.]). For the structure of a related compound, see: Guo, Liu & Yang (2013[Guo, Y. Z., Liu, J. G. & Yang, S. Y. (2013). Acta Cryst. E69, o226.]) and for its synthesis, see: Hall et al. (1982[Hall, H. K., Nogues, P., Rhoades, J. W., Sentman, R. C. & Detar, M. (1982). J. Org. Chem. 47, 1451-1455.]); Guo et al. (2012[Guo, Y. Z., Song, H. W., Zhai, L., Liu, J. G. & Yang, S. Y. (2012). Polym. J. 44, 718-723.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13ClO6

  • Mr = 348.72

  • Triclinic, [P \overline 1]

  • a = 6.8988 (15) Å

  • b = 9.140 (2) Å

  • c = 11.950 (3) Å

  • [alpha] = 80.937 (9)°

  • [beta] = 75.365 (8)°

  • [gamma] = 79.614 (8)°

  • V = 712.1 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 173 K

  • 0.41 × 0.21 × 0.15 mm

Data collection
  • Rigaku Saturn724+ CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.] Tmin = 0.702, Tmax = 1.000

  • 9192 measured reflections

  • 3238 independent reflections

  • 3034 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.108

  • S = 1.10

  • 3238 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3B...O4i 0.99 2.51 3.420 (2) 153
C5-H5...O1ii 1.00 2.59 3.386 (2) 136
C7-H7...O4i 1.00 2.51 3.468 (2) 160
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2008)[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]; cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2004 ).


Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 51173188).

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Guo, Y. Z., Liu, J. G. & Yang, S. Y. (2013). Acta Cryst. E69, o226.  [CSD] [CrossRef] [IUCr Journals]
Guo, Y. Z., Shen, D. X., Ni, H. J., Liu, J. G. & Yang, S. Y. (2013). Prog. Org. Coat. 76, 768-777.  [Web of Science] [CrossRef] [ChemPort]
Guo, Y. Z., Song, H. W., Zhai, L., Liu, J. G. & Yang, S. Y. (2012). Polym. J. 44, 718-723.  [Web of Science] [CrossRef] [ChemPort]
Hall, H. K., Nogues, P., Rhoades, J. W., Sentman, R. C. & Detar, M. (1982). J. Org. Chem. 47, 1451-1455.  [CrossRef] [ChemPort]
Li, X. D., Zhong, Z. X., Han, S. H., Lee, S. H. & Lee, M. H. (2005). Polym. Int. 54, 406-411.  [Web of Science] [CrossRef] [ChemPort]
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.  [Web of Science] [CrossRef] [ChemPort]
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Zhang, A. Q., Li, X. D., Nah, C. W., Hwang, K. J. & Lee, M. H. (2003). J. Polym. Sci. Part A Polym. Chem. 41, 22-29.  [CrossRef] [ChemPort]
Zhong, Z. X., Li, X. D., Lee, S. H. & Lee, M. H. (2004). Mol. Cryst. Liq. Cryst. 425, 145-152.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1031-o1032   [ doi:10.1107/S1600536813014943 ]

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