Synthesis and Crystal Structure of 2-Ethylamino-6H-5-(1-phenyl-3- methyl/phenyl-5-pyrazolone-4-ylene)-1,3,4-Thiadiazine

Abstract

Abstract: 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-pyrazolone-5 with 4-ethylthiosemicarbazide. The title compounds were characterized by elemental analysis, IR, ¹H NMR, 13C 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= 0.794 7(1) nm, b= 0.834 8(1) nm, c=1.199 0(2) nm, β=106.07(1)°, V=0.772 69(2) nm³, Z=2, D_c=1.356 g/cm³, μ=0.219 mm^-1, F(000)=332, R=0.029 8, wR=0.070 4. 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 6(4) nm³, Z=4, D_c=1.345 g/cm³, μ=0.194 mm^-1, F(000)=792, R=0.034 5, wR= 0.069 4. 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.

Key words: Condensation reaction, Heterocycles, Crystal structure, Supramolecular structure

CLC Number:

O621

TrendMD:

PENG Bang-Hua, LIU Guang-Fei, LIU Lang, JIA Dian-Zeng, YU Kai-Bei . Synthesis and Crystal Structure of 2-Ethylamino-6H-5-(1-phenyl-3- methyl/phenyl-5-pyrazolone-4-ylene)-1,3,4-Thiadiazine[J]. Chem. J. Chinese Universities, 2004, 25(12): 2278.

References

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