Crystal structure of N-[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]-2-chloroacetamide

In the title compound, C9H9ClN4OS, the dihedral angle between the acetamide moiety and the pyridine ring is 4.83 (12)°. The O=C—C—Cl torsion angle is 46.4 (3)° and an intramolecular C—H⋯O interaction generates an S(6) ring. In the crystal, molecules are linked by N—H⋯O, N—H⋯N and C—H⋯N hydrogen bonds, generating sheets lying parallel to (120).


S1. Comment
Pyridine compounds have occupied a unique position in medicinal and industrial chemistry. Some polyfuctional pyridines constitute an important class of antitumor compounds (Boger & Nakahara, 1991;Zhang et al., 1995). They also show antibacterial (Castedo et al., 1984), antifungal (Latif et al., 1981), antimyotic (Mamolo et al., 2001) and antidepressant (Gachet et al., 1995) activities. In this respect, and also in continuation of our study on synthesis of different heterocyclic system that containing highly biological activity, we report here the synthesis and crystal structur of the title compound.
In the title compound ( Fig. 1), the chloroacetamide moiety has an extended conformation, as indicated by the torsion

Figure 2
View of the hydrogen bonding and packing of the title compound viewed along the a axis. Packing of the title compound viewed along the b axis.

N-[4-Amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]-2-chloroacetamide
Crystal data Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq  (17)