| Summary: | Two penta-coordinated <b>[Co(<sup>Morph</sup>BPT)Cl<sub>2</sub>]</b>; <b>1</b> and <b>[Co(<sup>Pip</sup>BPT)Cl<sub>2</sub>]</b>; <b>2</b> complexes with the <i>bis</i>-pyrazolyl-<i>s</i>-triazine pincer ligands <b><sup>Morph</sup>BPT</b> and <b><sup>Pip</sup>BPT</b> were synthesized and characterized. Both <b><sup>Morph</sup>BPT</b> and <b><sup>Pip</sup>BPT</b> act as NNN-tridentate pincer chelates coordinating the Co(II) center with one short Co-N(<i>s</i>-triazine) and two longer Co-N(pyrazole) bonds. The coordination number of Co(II) is five in both complexes, and the geometry around Co(II) ion is a distorted square pyramidal in <b>1,</b> while <b>2</b> shows more distortion. In both complexes, the packing is dominated by Cl…H, C-H…π, and Cl…C (anion-π stacking) interactions in addition to O…H interactions, which are found only in <b>1</b>. The UV-Vis spectral band at 564 nm was assigned to metal–ligand charge transfer transitions based on TD-DFT calculations. Complexes <b>1</b> and <b>2</b> showed higher antimicrobial activity compared to the respective free ligand <b><sup>Morph</sup></b><b>BPT</b> and <b><sup>Pip</sup>BPT,</b> which were not active. MIC values indicated that <b>2</b> had better activity against <i>S. aureus, B. subtilis</i>, and <i>P. vulgaris</i> than <b>1</b>. DPPH free radical scavenging assay revealed that all the studied compounds showed weak to moderate antioxidant activity where the nature of the substituent at the <i>s</i>-triazine core has a significant impact on the antioxidant activity.
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