2-[(2-Azaniumylethyl)carbamoyl]phenolate–phenol (1/1)

In the title 1:1 adduct, C9H12N2O2·C6H6O, the dihedral angle between the benzene ring and the salicylic amide group is 6.68 (6)°. The conformation of the amide group is supported by two intramolecular N—H⋯O hydrogen bonds, which close S(6) and S(7) rings. In the crystal, the components are linked by O—H⋯O and N—H⋯O hydrogen bonds, generating (100) sheets.

In the title 1:1 adduct, C 9 H 12 N 2 O 2 ÁC 6 H 6 O, the dihedral angle between the benzene ring and the salicylic amide group is 6.68 (6) . The conformation of the amide group is supported by two intramolecular N-HÁ Á ÁO hydrogen bonds, which close S(6) and S(7) rings. In the crystal, the components are linked by O-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds, generating (100) sheets.
Thanks are due to MESRS and ATRST (Ministé re de l'Enseignement Supé rieur et de la Recherche Scientifique et la direction gé né rale de la recherche -Algeria) for financial support.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7050). Salicylic amide with its diverse amidic forms namely ethylelenediamine or other amines were found to be as good chelating agents currently applied in coordination chemistry (Koch, 2001;Hancock et al., 1989).
The molecule structure of (I), is illustrated in Fig. 1. In the title structure the phenol molecule is cocrystalized with ethylenediamine Salicylic amide The crystal packing can be described by layers parallel to (100) Table 1). These interactions link the molecules within the layers and also link the layers together.
Experimental 0.06 g (1 mmol) ethylenediamine was dissolved in 20 ml of methanol. To this methanolic solution 0.214 g (1 mmol) of phenyl salicylate were added in one portion. This mixture was stirred for one hour at room temperature, and then 0.172 g (1 mmol) of 2-hydroxynaphtaldehyde were also added and heated to 60 °C for 4 h. The solid obtained was recovered by filtration after reducing of its volume on vaccum with rotating evaporator to obtain colourless prisms.

Refinement
The H atoms were localized on Fourier maps but introduced in calculated positions and treated as riding on their parent atom (C,O and N) with C-H = 0.97 Å (ethylene)or 0.93 Å (aromatic), O-H = 0.82 Å and N-H = 0.86 Å or 0.89 Å (ammonium); with U iso (H) = 1.2U eq (ammonium and hydroxy) and U iso (H) = 1.5U eq .

Computing details
Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008  The asymmetric unit of (I) with displacement ellipsoids drawn at the 50% probability level.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.