Copyright © Mansor et al. 2008
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received August 11, 2008; Accepted August 11, 2008.
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Molecules of the title compound, C14H8N2O5, are linked by a hydroxy–amide O—HO hydrogen bond into a linear chain. The hydroxy group is disordered over two positions of the benzene ring in an approximate 0.57:0.43 ratio.
Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).
We thank MOSTI (grant No. 14–02-03–4014) and the University of Malaya for supporting this study.
supplementary crystallographic information
4-Nitrophthalic anhydride (5.0 g, 26 mmol) and o-hydroxyaniline (3.4 g, 31 mmol) were heated in glacial acetic acid (15 mol) for 4 h at 393–401 K. The reaction was shown to be complete by thin layer chromatography. The mixture was poured into water. The yellow solid was collected in 90% yield; purification was effected by recrystallization from chloroform.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The hydroxy group is disordered over two positions on the phenylene ring; the disorder refined to a 0.571 (1):429 (1) ratio.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
J Org Chem. 2007 Mar 30; 72(7):2392-401.[J Org Chem. 2007]