[Journal logo]

Volume 68 
Part 1 
Page o121  
January 2012  

Received 2 December 2011
Accepted 7 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.093
Data-to-parameter ratio = 16.0
Details
Open access

2-(2-Carboxyethyl)-1,3-dioxoisoindoline-5,6-dicarboxylic acid methanol monosolvate

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
Correspondence e-mail: Manuel.Fernandes@wits.ac.za

In the title compound, C13H9NO8·CH3OH, the main molecule possesses three carboxylic acid groups, which are asymmetrically distributed around the molecule core. This results in hydrogen-bonding motifs ranging from a chain to various rings. The combination of the chain motif together with a carboxylic dimer R22(8) ring motif creates a ribbon of molecules propagating along the c-axis direction. A second ribbon results from the combination of the chain motif together with a methanol solvent molecule and carboxyl-containing R44(12) ring motif. These two ribbons combine alternately, forming a hydrogen-bonded layer of molecules parallel to (2[\overline{1}]0).

Related literature

For applications of charge-transfer complexes composed of pyromellitic anhydrides or their imides or polyimide derivatives, see: Barooah et al. (2006[Barooah, N., Sarma, R. J. & Baruah, J. B. (2006). CrystEngComm, 8, 608-615.]); Kim et al. (2002[Kim, Y.-H., Ahn, S.-K., Kim, H. S. & Kwon, S.-K. (2002). J. Polym. Sci. Part A: Polym. Chem. 40, 4288-4296.]); O'Brien et al. (1988[O'Brien, K. C., Koros, W. J. & Husk, G. R. (1988). J. Membr. Sci. 35, 217-230.]); Dingemans et al. (2004[Dingemans, T. J., Picken, S. J., Murthy, N. S., Mark, P., StClair, T. L. & Samulski, E. T. (2004). Chem. Mater. 16, 966-974.]); Zheng et al. (2008[Zheng, Q., Huang, J., Sarjeant, A. & Katz, H. E. (2008). J. Am. Chem. Soc. 130, 14410-14411.]). For an example of another asymmetrically substituted diimide, see: Zhu et al. (2010[Zhu, Z., Cardin, C. J., Gan, Y. & Colquhoun, H. M. (2010). Nat. Chem. 2, 653-660.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the REAXYS database, see: Elsevier (2011[Elsevier (2011). REAXYS. Elsevier Properties SA.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9NO8·CH4O

  • Mr = 339.25

  • Triclinic, [P \overline 1]

  • a = 8.7830 (3) Å

  • b = 9.7262 (3) Å

  • c = 9.9157 (3) Å

  • [alpha] = 66.164 (2)°

  • [beta] = 72.830 (2)°

  • [gamma] = 77.926 (2)°

  • V = 736.35 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 173 K

  • 0.44 × 0.14 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 11822 measured reflections

  • 3549 independent reflections

  • 2193 reflections with I > 2[sigma](I)

  • Rint = 0.053

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

  • wR(F2) = 0.093

  • S = 0.89

  • 3549 reflections

  • 222 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.84 1.84 2.6784 (17) 172
O5-H5...O4ii 0.84 1.88 2.7181 (15) 178
O7-H7...O9iii 0.84 1.71 2.5360 (17) 168
O9-H9...O8 0.84 1.87 2.7014 (17) 169
Symmetry codes: (i) -x+2, -y+2, -z-1; (ii) x, y, z+1; (iii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and SCHAKAL99 (Keller, 1999[Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2403 ).


Acknowledgements

This work was supported by the National Research Foundation, Pretoria (NRF, GUN 77122) and the University of the Witwatersrand.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Barooah, N., Sarma, R. J. & Baruah, J. B. (2006). CrystEngComm, 8, 608-615.  [ISI] [CSD] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dingemans, T. J., Picken, S. J., Murthy, N. S., Mark, P., StClair, T. L. & Samulski, E. T. (2004). Chem. Mater. 16, 966-974.  [ISI] [CrossRef] [ChemPort]
Elsevier (2011). REAXYS. Elsevier Properties SA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.
Kim, Y.-H., Ahn, S.-K., Kim, H. S. & Kwon, S.-K. (2002). J. Polym. Sci. Part A: Polym. Chem. 40, 4288-4296.
O'Brien, K. C., Koros, W. J. & Husk, G. R. (1988). J. Membr. Sci. 35, 217-230.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zheng, Q., Huang, J., Sarjeant, A. & Katz, H. E. (2008). J. Am. Chem. Soc. 130, 14410-14411.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhu, Z., Cardin, C. J., Gan, Y. & Colquhoun, H. M. (2010). Nat. Chem. 2, 653-660.  [CSD] [CrossRef] [PubMed]


Acta Cryst (2012). E68, o121  [ doi:10.1107/S1600536811052755 ]

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.