3-溴-5-氯水杨醛缩邻氯苯胺的合成及晶体结构研究

Synthesis and characterization of a Schiff base from 3-bromo-5-chlorosalicylaldehyde and o-chloroaniline

目的合成一种新的3-溴-5-氯水杨醛Schiff碱。方法以3-溴-5-氯水杨醛和邻氯苯胺为原料合成一种新的Schiff碱,用X-射线单晶衍射法对其结构进行表征。结果标题化合物属于单斜晶系,空间群P21/c,晶胞参数a=0.824 62(16)nm,b=1.397 7(3)nm,c=1.143 1(2)nm,β=104.30(3)°,V=1.276 8(4)nm3,Dc=1.795 g/cm3,Z=4,μ=3.622 mm-1,F(000)=680,R=0.031 8,wR=0.065 6。结论标题化合物以C7 N1为中心呈E构型,C N双键使得整个结构趋于共面,2个芳香环之间的二面角为4.65(1)°。此外,化合物中存在的分子内氢键、分子间氢键及分子间卤素-卤素作用将分子链成一个三维超分子网络结构。

Aim To synthesize a new Schiff base which derived from 3-bromo-5-chlorosalicylaldehyde.Methods The compound was obtained by condensation reaction using 3-bromo-5-chlorosalicylaldehyde and o-chloroaniline as raw material.The structure of the compound was characterized by X-ray single crystal diffraction.Results The results show that the compound crystallizes in monoclinic,space group P21 c with cell parameter of a=0.824 62（16） nm,b=1.397 7（3） nm,c=1.143 1（2） nm,β=104.30（3）°,V=1.276 8（4） nm3,Dc= 1.795 g/cm3,Z=4,μ=3.622 mm-1,F（000）=680,R=0.031 8 and wR=0.065 6.Conclusion The molecule of the title compound displays an E configuration with respect to the imine C7N1 double bond.The CN double bond make aromatic rings coplanar,forming a dihedral angle of 7.9（2）°.Another,the intramolecular and intermolecular as well as halogen…halogen interactions assemble the molecules into a three-dimensional supermolecular network.