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

Ge, C.; Li, X.; Zhang, X.; Zhao, Y.; Zhang, R.

doi:10.1107/S1600536809035107

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 (C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.039
wR = 0.111
Data-to-parameter ratio = 13.5
Details

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

Chunhua Ge,^a ^* Xiangqian Li,^a Xiangdong Zhang,^a Yang Zhao ^a and Rui Zhang ^a

^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-HO 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-HO hydrogen bonds.

Related literature

For recent developments in the chemistry of naphthalene diimides, see Bhosale et al. (2008). For pyromellitic diimides, see: Gabriel & Iverson (2002); Ghosh & Ramakrishnan (2005); Kimizuka et al. (1995). For details of the synthesis, see Barooah et al. (2006).

Experimental

Crystal data

C₁₄H₈N₂O₈·2C₃H₇NO
M_r = 478.42
Monoclinic, P 2₁ /c
a = 7.7470 (15) Å
b = 9.3100 (19) Å
c = 16.334 (5) Å
= 104.02 (3)°
V = 1143.0 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.958, T_max = 0.973
6227 measured reflections
2236 independent reflections
1910 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.111
S = 1.06
2236 reflections
166 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3AO5A	0.82	1.72	2.526 (2)	166
O4-H4BO5B	0.82	1.70	2.496 (2)	162
C2-H2AO3ⁱ	0.97	2.41	3.230 (2)	142
C6-H6O1ⁱⁱ	0.93	2.50	3.414 (2)	166
C9-H9AO2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Bhosale, S. V., Jani, C. H. & Langford, S. J. (2008). Chem. Soc. Rev. 37, 331-342.
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.
Ghosh, S. & Ramakrishnan, S. (2005). Angew. Chem. Int. Ed. 44, 5441-5447.
Kimizuka, N., Kawasaki, T., Hirata, K. & Kunitake, T. (1995). J. Am. Chem. Soc. 117, 6360-6361.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds