3,14-Dimethyl-2,6,13,17-tetra-aza-tricyclo-[16.4.0.0]docosa-ne-(naphthalen-1-yl)methanol (1/2)

Abstract

In the title co-crystal, C(20)H(40)N(4)·2C(11)H(10)O, the macrocycle is generated by a crystallographic inversion centre. The N atoms show a pyramidal coordination, and the cyclo-hexane ring that is fused to the 14-membered C(10)N(4) ring exists in a chair conformation, whereas the methyl substituent occupies an axial site. The (naphthalen-1-yl)methanol mol-ecule forms an O-H⋯N hydrogen bond to a cyclam N atom. The mean-square-plane passing through the 14-membered ring is approximately coplanar with the naphthalene fused-ring [dihedral angle = 6.6 (1)°].

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of C20H40N4.2C11H10O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.