2,2′-[1,2-Phenylenebis(azanediyl)]diacetonitrile

The title compound, C10H10N4, shows chemical but not crystallographic C 2 symmetry. The two cyanomethyl groups are located in an anti position with respect to the aromatic ring. In the crystal, molecules form parallel ladder-like tapes linked through two N—H⋯N hydrogen bonds. Further weak intramolecular N—H⋯N hydrogen bonding is responsible for the elongation of one of the Caromatic—N bonds.

The title compound, C 10 H 10 N 4 , shows chemical but not crystallographic C 2 symmetry. The two cyanomethyl groups are located in an anti position with respect to the aromatic ring. In the crystal, molecules form parallel ladder-like tapes linked through two N-HÁ Á ÁN hydrogen bonds. Further weak intramolecular N-HÁ Á ÁN hydrogen bonding is responsible for the elongation of one of the C aromatic -N bonds.

Experimental
Thus, these results indicate that the intramolecular interaction is responsible for the C3-N1 bond elongation. This is confirmed by the N1-C7 bond length [1.4648 (18)

Experimental
A mixture of potassium cyanide (0.260 g, 4.00 mmol) and N 1 ,N 2 -bis((1H-benzotriazol-1-yl)methyl)benzene-1,2-diamine (0.370 g, 1.00 mmol) was stirred at room temperature in DMSO (5 ml) for 6 h. After quenching by addition of aqueous ammonium chloride a solid formed which was separated and extracted with ethyl acetate.The organic extract was sequentially washed with saturated Na 2 CO 3 solution and water, then dried (Na 2 SO 4 ), filtered, and concentrated to give a solid homogeneous by TLC (80% EtOAc/benzene) in 82% yield. Single crystals were obtained by recrystallization from chloroform/methanol by slow evaporation of the solvent at room temperaature, m.p. 399-400 K.

Refinement
All hydrogen atoms were discernible in difference Fourier maps and could be refined to reasonable geometry, but according to common practice H atoms bonded to C were kept in ideal positions with C-H = 0.96 Å. The coordinates of the amino H atoms were refined. U iso (H) was set to 1.2U eq (C,N). All non-hydrogen atoms were refined using harmonic refinement. used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figure 1
A view of the crystal structure of the tittle compund (I) with the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. 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.