N-(2-aminophenyl)-2-(2-isopropylphenoxy) acetamide(3) has been synthesized in good yield by stirring compound ethyl 2-(2-isopropylphenoxy) acetic acid(1), with, 2-diaminobenzene (2), in dry dichloromethane followed by the addition of lutidine, and TBTU in cooled condition. The crude product (3) was recrystallized and elucidated by elemental analyses and spectroscopic techniques (HNMR, LC-MS). The anticancer activity was confirmed by in silico modeling study which targets the VEGFr receptor. The compound crystallizes in the orthorhombic crystal system with space group Pbca with unit cell parameters: a = 7.4250 (4) Å, b = 14.9753 (7) Å, c = 27.5656 (14) Å and Z = 4. The crystal structure has been solved by using direct methods and refined by full matrix least-squares procédures to a final R-factor of 0.042 for 2158 observed reflections. The structure exhibits intermolecular H-bonds of the type N–H⋅⋅⋅O. In addition, two intramolecular interactions N1-H1…O2 and N2-H2B…N1 were also observed.

Crystallization induced emission is observed for bis-pyridyl-ethyl-di-imine and bis-pyridyl-butyl-di-imine. While in case of bis-pyridyl-di-imines, with no alkyl spacer, the quenching is observed in the solid state.

In the title compound, C(16)H(16)ClNO(2)S(2), the piperidine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.5 (1)°. In the crystal, a weak C-H⋯O hydrogen bond links mol-ecules into chains along [001]. In addition, π-π stacking inter-actions are present involving the benzene and pyran rings, with a centroid-to-centroid distance of 3.712 (2) Å. The crystal studied is a nonmerohedral twin with refined components 0.221 (1) and 0.779 (1).