Synthesis and crystal structure of N-(1'-H-pyrrol-2'-ylcarbonyl)-5-amino-1,10-phenanthroline

The title compound, N-(1'-H-pyrrol-2'-ylcarbonyl)-5-amino-1,10-phenanthroline was synthesized by the reaction of alpha-pyrrolyl carbonyl chloride and 5-amino-1,10-phenanthroline in pyridine. Determined by X-ray structure analysis, it crystallizes in triclinic system, space group Pi with the following crystallographic data: C20H21N5O3, M-r = 379.42, a = 7.8559(4), b = 9.1681(6), c = 14.6818(9) angstrom, alpha= 73.254(10), beta = 88.938(15), gamma= 68.080(10)degrees, V = 934.66(10) angstrom(3), Z = 2, F(000) = 400, D-c = 1.348 g/cm(3) and mu = 0.094 mm(-1). The final R = 0.0680 and wR = 0.1419 for 2142 observed reflections with I > 2 sigma(I), and R = 0.1084 and wR = 0.1643 for all reflections. Two aromatic ring planes (pyrrole and phenanthroline rings) are connected by the amide plane. Two different types of intermolecular hydrogen bonds, O-H center dot center dot center dot N and N-H center dot center dot center dot O, exist in the crystal. The title complex molecules are connected through hydrogen bonds and weak pi-pi stacking interactions to generate a 3-D supramolecule.