[Journal logo]

Volume 65 
Part 10 
Page o2400  
October 2009  

Received 25 August 2009
Accepted 1 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.039
wR = 0.111
Data-to-parameter ratio = 13.5
Details
Open access

2,2'-(1,3,5,7-Tetraoxo-1,2,3,5,6,7-hexahydropyrrolo[3,4-f]isoindole-2,6-diyl)diacetic acid N,N-dimethylformamide disolvate

aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
Correspondence e-mail: chhge@lnu.edu.cn

The asymmetric unit of the title compound, C14H8N2O8·2C3H7NO or L·2DMF (DMF = N,N-dimethylformamide), contains one half of the centrosymmetric molecule L and one solvent molecule, which is disordered between two orientations in a 0.555 (4):0.445 (4) ratio. Intermolecular O-H...O hydrogen bonds link one L and two DMF molecules into a centrosymmetric hydrogen-bonded cluster. The crystal packing is further stabilized by weak intermolecular C-H...O hydrogen bonds.

Related literature

For recent developments in the chemistry of naphthalene diimides, see Bhosale et al. (2008[Bhosale, S. V., Jani, C. H. & Langford, S. J. (2008). Chem. Soc. Rev. 37, 331-342.]). For pyromellitic diimides, see: Gabriel & Iverson (2002[Gabriel, G. J. & Iverson, B. L. (2002). J. Am. Chem. Soc. 124, 15174-15175.]); Ghosh & Ramakrishnan (2005[Ghosh, S. & Ramakrishnan, S. (2005). Angew. Chem. Int. Ed. 44, 5441-5447.]); Kimizuka et al. (1995[Kimizuka, N., Kawasaki, T., Hirata, K. & Kunitake, T. (1995). J. Am. Chem. Soc. 117, 6360-6361.]). For details of the synthesis, see Barooah et al. (2006[Barooah, N., Sarma, R. J. & Baruah, J. B. (2006). CrystEngComm, 8, 608-615.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8N2O8·2C3H7NO

  • Mr = 478.42

  • Monoclinic, P 21 /c

  • a = 7.7470 (15) Å

  • b = 9.3100 (19) Å

  • c = 16.334 (5) Å

  • [beta] = 104.02 (3)°

  • V = 1143.0 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.25 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Göttingen, Germany.]) Tmin = 0.958, Tmax = 0.973

  • 6227 measured reflections

  • 2236 independent reflections

  • 1910 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.111

  • S = 1.06

  • 2236 reflections

  • 166 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O5A 0.82 1.72 2.526 (2) 166
O4-H4B...O5B 0.82 1.70 2.496 (2) 162
C2-H2A...O3i 0.97 2.41 3.230 (2) 142
C6-H6...O1ii 0.93 2.50 3.414 (2) 166
C9-H9A...O2iii 0.96 2.57 3.432 (3) 149
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2607 ).


Acknowledgements

This work was supported by the Project for Innovation Teams of Liaoning Province, China (No. 2007 T052), the Project for Provincial Key Laboratories of Liaoning Province, China (No. 2008S104) and the Doctoral Startup Project, Liaoning University.

References

Barooah, N., Sarma, R. J. & Baruah, J. B. (2006). CrystEngComm, 8, 608-615.  [ISI] [CSD] [CrossRef] [ChemPort]
Bhosale, S. V., Jani, C. H. & Langford, S. J. (2008). Chem. Soc. Rev. 37, 331-342.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gabriel, G. J. & Iverson, B. L. (2002). J. Am. Chem. Soc. 124, 15174-15175.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ghosh, S. & Ramakrishnan, S. (2005). Angew. Chem. Int. Ed. 44, 5441-5447.  [ISI] [CrossRef] [ChemPort]
Kimizuka, N., Kawasaki, T., Hirata, K. & Kunitake, T. (1995). J. Am. Chem. Soc. 117, 6360-6361.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2009). E65, o2400  [ doi:10.1107/S1600536809035107 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.