(4Z,6Z,12Z,14Z)-2,10-Dimethyl-2,8,10,16-tetrahydrodipyrazolo[3,4-e:3′,4′-l][1,2,4,8,9,11]hexaazacyclotetradecine-4,12-diamine

The title compound, C12H16N12, is a centrosymmetric molecule which comprises of a hexaaza[14]annulene macrocyclic ring fused with two pyrazole rings. The macrocyclic ring is essentially planar, with an r.m.s. deviation of 0.0381 Å. The electron pairs of the amino groups are delocalized with the conjugated system of the macrocycle. Strong intramolecular N—H⋯N hydrogen bonds arranged in an S 2 2(10) graph-set motif are present in the macrocyclic ring. In the crystal, the amino groups act as donors for intermolecular N—H⋯N interactions with the N atoms of the heterocyclic system, forming a network of two types of extended chains oriented parallel to the [101] and [011] directions. The crystal packing is also stabilized by weak intermolecular C—H⋯N hydrogen bonds formed between pyrazole C—H groups and N atoms of the macrocyclic ring, running in the [10] direction.

The title compound, C 12 H 16 N 12 , is a centrosymmetric molecule which comprises of a hexaaza [14]annulene macrocyclic ring fused with two pyrazole rings. The macrocyclic ring is essentially planar, with an r.m.s. deviation of 0.0381 Å . The electron pairs of the amino groups are delocalized with the conjugated system of the macrocycle. Strong intramolecular N-HÁ Á ÁN hydrogen bonds arranged in an S 2 2 (10) graph-set motif are present in the macrocyclic ring. In the crystal, the amino groups act as donors for intermolecular N-HÁ Á ÁN interactions with the N atoms of the heterocyclic system, forming a network of two types of extended chains oriented parallel to the [101] and [011] directions. The crystal packing is also stabilized by weak intermolecular C-HÁ Á ÁN hydrogen bonds formed between pyrazole C-H groups and N atoms of the macrocyclic ring, running in the [101] direction.
In the crystal, the amino groups act as donors for intermolecular N-H···N interaction with the nitrogen atoms N1 (N1A) and N6 (N6A), thereby forming two types of extended chains. The nitrogen atoms N1 (N1A) are acceptors in C (6)

Experimental
The title compound was synthesized according to Dolzhenko et al. (2009). Single crystals suitable for crystallographic analysis were grown by recrystallization from methanol.

Refinement
All the H atoms attached to the carbon atoms were constrained in a riding motion approximation [0.94 Å for C aryl -H and 0.97 Å for methyl groups; U iso (H) =1.2U eq (C aryl ) and U iso (H) =1.5U eq (C methyl )] while the N-bound H atoms were located in a difference map and refined freely.
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. (4Z,6Z,12Z,14Z)-2,10-Dimethyl-2,8,10,16-tetrahydrodipyrazolo[3,4-e:3',4'l] [1,2,4,8,9,11] 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 Rfactors(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.