Abstract
The title azo compound, C16H16N4, was synthesized from 2,6-di-methyl-aniline. The diazenyl group adopts a trans (E) conformation, with an N=N bond length of 1.265 (4) Å. The pyrazole ring is approximately planar. In the crystal, zigzag chains along the b-axis direction with a C(3) is graph-set motif are formed by N-H⋯N hydrogen bonds involving the pyrazole moiety.
Highlights
The title azo compound, C16H16N4, was synthesized from 2,6-dimethylaniline
Zigzag chains along the b-axis direction with a C(3) is graph-set motif are formed by N—HÁ Á ÁN hydrogen bonds involving the pyrazole moiety
The molecular structure of the title compound is composed of a benzene ring linked to an indazole unit by an N N bond
Summary
The molecular structure of the title compound is composed of a benzene ring linked to an indazole unit by an N N bond. The molecule is practically flat with a maximum deviation of 0.142 (5) A (for atom C7) from the mean plane passing through the non-H atoms. The pyrazole ring (N3/N4/C15/C10/ C9) is approximately planar with an r.m.s. deviation of 0.0026 A. The C—C bond lengths of the pyrazole ring are 1.404 (6) and 1.428 (5) A , the C—N bond lengths are 1.322 (5) and 1.359 (5) Aand the N—N bond length is 1.351 (4) A , in good agreement with values reported previously for 7-methyl1H-indazole [1.400 (4), 1.422 (4), 1.320 (4), 1.366 (3) and 1.356 (3) A , respectively; Foces-Foces, 2005]. Cg1 and Cg2 are the centroids of the C9–C14 and C9–C10/C15/N3–N4 rings, respectively. Symmetry codes: (i) Àx + 1, y + 12, Àz; (ii) x, y À 1, z
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