3,4,6-Triamino-N-phenylthieno[2,3-b]pyridine-2-carboxamide

In the title compound, C14H13N5OS, the dihedral angle between the fused ring system (r.m.s. deviation = 0.028 Å) and the phenyl ring is 48.24 (4)°. The molecule features both an intramolecular N—H⋯O and an N—H⋯N hydrogen bond. In the crystal, molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, generating a three-dimensional network. A weak N—H⋯π interaction is also observed.

In the title compound, C 14 H 13 N 5 OS, the dihedral angle between the fused ring system (r.m.s. deviation = 0.028 Å ) and the phenyl ring is 48.24 (4) . The molecule features both an intramolecular N-HÁ Á ÁO and an N-HÁ Á ÁN hydrogen bond. In the crystal, molecules are linked by N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds, generating a three-dimensional network. A weak N-HÁ Á Á interaction is also observed.
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
Supporting information for this paper is available from the IUCr electronic archives (Reference: HB7235).

Comment
Thienopyridines and their analogs are an interesting class of molecules due to their extensive spectrum of pharmacological properties, for example anti-inflammatory (Boschelli et al., 2008), anti-microbial (Bakhite et al., 2002) and anti-viral (Schnute et al., 2007) activities. As part of our program in the development of new heterocyclic molecules with potential bioactivities, we report in this study the synthesis and crystal structure determination of the title compound.
In the title compound, the fused ring system is nearly planar with an r.m.s. deviation of 0.028 Å and makes a dihedral angle of 48.24 (4)° with the terminal phenyl group. The conformation of the carboxamide group is partially determined by the intramolecular N4-H4B···O1 hydrogen bond ( Fig. 1 and Table 1). In the solid, the molecules associate through pairwise intermolecular N4-H4B···O1 and single N3-H3a···N1 hydrogen bonds to form a three-dimensional network (Figs. 2 and 3 and Table 1). A weak N-H···π interaction is observed between the NH 2 group (N2-H2B) and the centroid of the C9-C14 phenyl ring.

Refinement
H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 Å) while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N-H = 0.91 Å following an initial round of refinement to check the validity of the peak assignments. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.  The title compound with 50% probability ellipsoids and with intramolecular hydrogen bonds shown as dotted lines.  Packing viewed parallel to (101). 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.