Received 3 June 2009
The title compound, C12H16N12, is a centrosymmetric molecule which comprises of a hexaazaannulene 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-HN hydrogen bonds arranged in an S22(10) graph-set motif are present in the macrocyclic ring. In the crystal, the amino groups act as donors for intermolecular N-HN interactions with the N atoms of the heterocyclic system, forming a network of two types of extended chains oriented parallel to the  and  directions. The crystal packing is also stabilized by weak intermolecular C-HN hydrogen bonds formed between pyrazole C-H groups and N atoms of the macrocyclic ring, running in the  direction.
The title compound was synthesized according to Dolzhenko et al. (2009). For the synthesis and crystal structure studies of related macrocyclic compounds (as nickel complexes), see: Gradinaru et al. (2001); Gerbeleu et al. (1991); Leovac et al. (1993) and references cited therein; Simonov et al. (1988). For a review of the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2181 ).
This work is supported by the National Medical Research Council, Singapore (NMRC/NIG/0020/2008) and the National University of Singapore (R-148-050-091-101/133).
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