Received 30 October 2012
The crystal structure of the title compound, C8H9NO3, features centrosymmetric dimers with two amide groups interconnected by a pair of almost linear N-HO hydrogen bonds. Through intermolecular O-HO interactions between phenolic hydroxy groups and carbonyl O atoms, these dimers are assembled into undulating hydrogen-bonded layers parallel to the  plane. Additionally, the anti-H(-N) atom of the primary amide group forms an intramolecular hydrogen bond to the O atom of the methoxy group. The amide group froms a dihedral angle of 12.6 (1)° with the phenyl ring.
Hydrogen-bonding packing patterns of primary amides are discussed by Eccles et al. (2011) and McMahon et al. (2005). A description of the Cambridge Crystallographic Database is given by Allen (2002). The question of the occurrence of very bent, intramolecular C-HO hydrogen bonds has been discussed by Desiraju (1996).
Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2083 ).
We thank Dr Volker Huch (Universität des Saarlandes) for the data collection.
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