6H,13H-5,12:7,14-Dimethanodinaphtho[2,3-d:2,3-i][1,3,6,8]tetraazecine

In the title compound, C24H20N4, obtained through the condensation of naphthalene-2,3-diamine with formaldehyde in methanol, the molecule is located on a special position of site symmetry -4. Due to symmetry considerations, the aromatic rings are strictly perpendicular to each other. In the crystal, molecules are linked by pairs of C—H⋯π interactions into columns along [110].

In the title compound, C 24 H 20 N 4 , obtained through the condensation of naphthalene-2,3-diamine with formaldehyde in methanol, the molecule is located on a special position of site symmetry 4. Due to symmetry considerations, the aromatic rings are strictly perpendicular to each other. In the crystal, molecules are linked by pairs of C-HÁ Á Á interactions into columns along [110].
Due to symmetry considerations the aromatic rings are strictly perpendicular to each other. In the crystal packing ( Fig.   2), the molecules are linked by a pair of C-H···π interactions (Table 1) into columns along [110].

Experimental
A solution of naphthalene-2,3-diamine (158 mg, 1 mmol) in methanol (10 ml) was added dropwise at 273 K to 5 ml of 37% aqueous formaldehyde. The reaction mixture was stirring at this temperature for 1 h and its completion was monitored by TLC. After completion, the contents were poured over cold water (10 ml). The resultant solid was isolated by filtration, washed with cold water, dried in vacuum and recrystallized from ethyl acetate to give the title compound with 28% yield. The melting point of the title structure is 484 K.

Refinement
The H atoms atoms were found in difference Fourier maps and their coordinates were refined freely. The isotropic atomic displacement parameters of hydrogen atoms were evaluated as 1.2×U eq of the parent atom. As the structure contains only light atoms, the Friedel-pair reflections were merged and the Flack parameter has not been determined.

Figure 1
A view of (I) with the numbering scheme, displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (i) 1 + y,1 -x,-z; (ii) 2 -x,-y,z; (iii) 1 -y,-1 + x,-z.   1,12,14,25-tetraazaheptacyclo[12.12.1.1 12,25 .0 2,11 .0 4,9 .0 15,24 .0 17,22 ]octacosa-2,4(9),5,7,10,15,17 (22),18, Special details Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F 2 for refinement carried out on F and F 2 , respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.