Adipic acid–2,4-diamino-6-(4-methoxyphenyl)-1,3,5-triazine (1/2)

The asymmetric unit of the title compound, 2C10H11N5O·C6H10O4, consists of a 2,4-diamino-6-(4-methoxyphenyl)-1,3,5-triazine molecule and one-half molecule of adipic acid which lies about an inversion center. The triazine ring makes a dihedral angle of 12.89 (4)° with the adjacent benzene ring. In the crystal, the components are linked by N—H⋯O and O—H⋯N hydrogen bonds, thus generating a centrosymmetric 2 + 1 unit of triazine and adipic acid molecules with R 2 2(8) motifs. The triazine molecules are connected to each other by N—H⋯N hydrogen bonds, forming an R 2 2(8) motif and a supramolecular ribbon along the c axis. The 2 + 1 units and the supramolecular ribbons are further interlinked by weak N—H⋯O, C—H⋯O and C—H⋯π interactions, resulting in a three-dimensional network.

The asymmetric unit of the title compound, 2C 10 H 11 N 5 OÁ-C 6 H 10 O 4 , consists of a 2,4-diamino-6-(4-methoxyphenyl)-1,3,5-triazine molecule and one-half molecule of adipic acid which lies about an inversion center. The triazine ring makes a dihedral angle of 12.89 (4) with the adjacent benzene ring. In the crystal, the components are linked by N-HÁ Á ÁO and O-HÁ Á ÁN hydrogen bonds, thus generating a centrosymmetric 2 + 1 unit of triazine and adipic acid molecules with R 2 2 (8) motifs. The triazine molecules are connected to each other by N-HÁ Á ÁN hydrogen bonds, forming an R 2 2 (8) motif and a supramolecular ribbon along the c axis. The 2 + 1 units and the supramolecular ribbons are further interlinked by weak N-HÁ Á ÁO, C-HÁ Á ÁO and C-HÁ Á Á interactions, resulting in a three-dimensional network.

Related literature
For the biological activity of triazine derivatives, see: Bork et al. (2003). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 Table 1 Hydrogen-bond geometry (Å , ).

Experimental
A hot methanol solution (20 ml) of 2,4-diamino-6-(4-methoxyphenyl)-1,3,5-triazine (54 mg Aldrich) and adipic acid (36 mg Loba) was warmed for a half an hour over a water bath. The resulting solution was allowed to cool slowly at room temperature. After a few days colourless block crystals were obtained.
A rotating-group model was used for the methyl group.

Figure 1
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Figure 2
The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity. 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.