An efficient synthesis of a novel N 3 O-type chelate and its Zn(II) complex is described. The Zn(II) complex shows C–H⋯Cl–Zn hydrogen bonding both in the solid and solution states. The chelate, (S,S)-[bis{(4-isopropyl-4,5-dihydrooxazol-2-yl)methyl}amino]acetic acid sodium salt, is a new and branched type of N 3 O ligand, featuring C 2 -symmetric bis(oxazoline)-N-carboxylate. A key step of the ligand synthesis involved a stepwise introduction of the oxazoline rings to suppress side products otherwise resulted from one-step approach. Treatment of the sodium bis(oxazoline)-N-carboxylate with ZnCl 2 and subsequent removal of NaCl resulted in the corresponding Zn(II) complex. The Zn(II) complex showed an unusual downfield shift by the isopropyl methine protons on its 1 H NMR spectrum, which suggests the C–H⋯Cl–Zn hydrogen bonding. An X-ray crystallographic analysis of the single crystals of the Zn(II) complex supports the C–H⋯Cl–Zn hydrogen bonding, showing a microchannel structure that encapsulates a linear array of chloroform molecules through other intermolecular hydrogen bonding interactions.