Synthesis and crystal structure of 2-ethylamino-6H-5-(1-phenyl-3-methyl/phenyl-5-pyriazolone-4-ylene)-1,3,4-thiadiazine

Two novel pyrazolone derivatives 2-ethylamino-6H-5-( 1-phenyl-3-methyl/phenyl-5-pyrazolone-4-ylene)-1, 3, 4-thiadiazine (PMCP-ETSC/DPCP-ETSC) containing NNS six-membered heterocycles were synthesized by the condensation reaction of 1-phenyl-3-methyl/phenyl-4-chloroacetyl-pyrazolone5 :with 4-ethylthiosemicarbazide. The title compounds were characterized by elemental analysis, IR, H-1 NMR, C-13 NMR and single-crystal X-ray diffraction. The crystal structure of PMCP-ETSC belongs to the monoclinic system, space group Pm with the lattice parameters a = 0.7947 (1) nm, b 0.834 8(1) nm, c = 1.199 0(2) nm, beta = 106.07(1)degrees, V = 0.772 69(2) nm(3), Z = 2, D-c = 1.356 g/cm(3), mu = 0.219 mm(-1), F (000) = 332, R = 0.0298, wR = 0.0704. The X-ray analysis showed that one-dimentional concatenate structure was formed along the c axis by the intermolecular. hydrogen bonds. The crystal of DPCP-ETSC belongs to the orthorhombic system, space group Pna2(1), and its lattice parameters are as follows: a = 1.147 8(2) nm, b = 1.354 5(2) nm, c = 1.199 4(2) nm, V = 1.864 60) nm(3), Z = 4, D-c = 1.345 g/cm(3), mu = 0.194 mm(-1), F(000) = 792, R = 0.0345, wR = 0.0694. The intermolecular hydrogen bonds led to the formation of chain-like one-dimensional compound along c axis and extended along ab plane to form the wave-like supramolecular structure.