N,N′-Dineopentylnaphthalene-1,8-diamine

In the title compound, C20H30N2, all bond distances and angles fall within the usual ranges but the C(ipso)—N distances [1.391 (5) and 1.398 (4) Å] are slightly shorter than the corresponding typical average distance of 1.42 (3) Å. The N atoms may be described as pyramidal sp 3-hybridized with an N—H⋯H—N separation of 2.07 (2) Å. This is necessitated because the two C(bridgehead)—C(ipso)—N—C torsion angles [170.6 (4) and 172.6 (3)°] would require the amine H atoms to be in prohibitively close proximity if the N atoms were assumed to be sp 2-hybridized.

In the title compound, C 20 H 30 N 2 , all bond distances and angles fall within the usual ranges but the C(ipso)-N distances [1.391 (5) and 1.398 (4) Å ] are slightly shorter than the corresponding typical average distance of 1.42 (3) Å . The N atoms may be described as pyramidal sp 3 -hybridized with an N-HÁ Á ÁH-N separation of 2.07 (2) Å . This is necessitated because the two C(bridgehead)-C(ipso)-N-C torsion angles [170.6 (4) and 172.6 (3) ] would require the amine H atoms to be in prohibitively close proximity if the N atoms were assumed to be sp 2 -hybridized.

Experimental
DAN ligands have also been examined in the realm of transition metal coordination chemistry (e.g. Lavoie et al., 2007, Bazinet et al., 2001b. Their titanium and zirconium complexes have been found to be effective catalysts for olefin polymerization (Lee et al., 2001).
In the structure of the title compound ( Fig. 1), all bond distances and angles fall in the usual ranges (Bruno et al., 2002).

Experimental
The title compound was obtained by treatment of 1,8-diaminonaphthalene with 2,2-dimethylpropanoyl chloride followed by LiAlH 4 reduction and aqueous work-up according to the procedure of Daniele et al. (2001). 1 H-and 13 C{ 1 H}-NMR data were in agreement with literature values. Needle-like crystals suitable for X-ray diffraction studies were obtained from a solution of the title compound stored at -20 °C in THF for several weeks.

Refinement
All non-amine H-atoms were placed in idealized locations and refined as riding with appropriate thermal displacement coefficients U iso (H) = 1.2 or 1.5 times U eq (bearing atom). The amine H atoms were refined with the N-H distances restrained supplementary materials sup-2 to 0.880 (1) Å and unconstrained thermal displacement coefficient. The refinement was performed with an 'anti-bumping' restraint. The Friedel pairs were merged. Fig. 1. The molecular structure of (I) with the thermal ellipsoids shown at 30% probability level.