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

Khorasani, S.; Fernandes, M.A.

doi:10.1107/S1600536811052755

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 (C-C) = 0.002 Å
R = 0.042
wR = 0.093
Data-to-parameter ratio = 16.0
Details

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

Sanaz Khorasani ^a and Manuel A. Fernandes ^a ^*

^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); Kim et al. (2002); O'Brien et al. (1988); Dingemans et al. (2004); Zheng et al. (2008). For an example of another asymmetrically substituted diimide, see: Zhu et al. (2010). For a description of the Cambridge Structural Database, see: Allen (2002). For the REAXYS database, see: Elsevier (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₃H₉NO₈·CH₄O
M_r = 339.25
Triclinic, $[P \overline 1]$
a = 8.7830 (3) Å
b = 9.7262 (3) Å
c = 9.9157 (3) Å
= 66.164 (2)°
= 72.830 (2)°
= 77.926 (2)°
V = 736.35 (4) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.093
S = 0.89
3549 reflections
222 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.84	1.84	2.6784 (17)	172
O5-H5O4ⁱⁱ	0.84	1.88	2.7181 (15)	178
O7-H7O9ⁱⁱⁱ	0.84	1.71	2.5360 (17)	168
O9-H9O8	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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

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organic compounds