Abstract
In the title compounds, C24H22BrN3, (I), and C24H22ClN3, (II), the 2-amino-pyridine ring is fused with a cyclo-heptane ring, which adopts a half-chair conformation. The planes of the phenyl and benzene rings are inclined to that of the central pyridine ring [r.m.s. deviations = 0.0083 (1) and 0.0093 (1) Å for (I) and (II), respectively] by 62.47 (17) and 72.51 (14)°, respectively, in (I), and by 71.44 (9) and 54.90 (8)°, respectively, in (II). The planes of the aromatic rings are inclined to one another by 53.82 (17)° in (I) and by 58.04 (9)° in (II). In the crystals of both (I) and (II), pairs of N-H⋯Nnitrile hydrogen bonds link the mol-ecules, forming inversion dimers with R 2 (2)(12) ring motifs. In (I), the resulting dimers are connected through C-H⋯Br hydrogen bonds, forming sheets parallel to (10-1), and π-π inter-actions [inter-centroid distance = 3.7821 (16) Å] involving inversion-related pyridine rings, forming a three-dimensional network. In (II), the resulting dimers are connected through π-π inter-actions [inter-centroid distance = 3.771 (2) Å] involving inversion-related pyridine rings, forming a two-dimensional network lying parallel to (001).
Highlights
In (II), the resulting dimers are connected through – interactions [intercentroid distance = 3.771 (2) Å] involving inversion-related pyridine rings, forming a two-dimensional network lying parallel to (001)
Pyridine is used in the pharmaceutical industry as a raw material for various drugs, vitamins and fungicides, and as a solvent (Shinkai et al, 2000; Jansen et al, 2001; Amr et al, 2006)
3-cyanopyridine compounds led us to synthesize the title compounds and we report on their crystal structures. doi:10.1107/S2056989014025936
Summary
The heterocyclic skeleton containing a nitrogen atom is the basis of many essential pharmaceuticals and of many physiologically active natural products. Molecules containing heterocyclic substructures continue to be attractive targets for synthesis since they often exhibit diverse and important biological properties. Pyridine is used in the pharmaceutical industry as a raw material for various drugs, vitamins and fungicides, and as a solvent (Shinkai et al, 2000; Jansen et al., 2001; Amr et al, 2006). Pyridines are omnipresent in medicaments and in agrochemicals (Tomlin, 1994). Pyridine derivatives have occupied a unique position in medicinal chemistry. 2-amino-3-cyanopyridines have been identified as IKK- inhibitors (Murata et al, 2003). Many fused cyanopyridines have been shown to have a wide spectrum of biological activity (Boschelli et al, 2004). Symmetry codes: (i) x; y þ 1; z; (ii) x þ 12; y þ 12; z þ 12
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