The 3-dimensional network of NH⋯N hydrogen bonds and Cl⋯Cl hydrogen contacts in the crystal structure of 2-(3′-chlorophenyl)imidazoline exhibits an anomalous hydrostatic compression. The lengthening of hydrogen bonds NH⋯N and some CH⋯N contacts as well as their supramolecular architecture lead to anomalous expansion of the crystal along [x] and [y] on increasing pressure to 0.1 GPa. The mechanism of this phenomenon is due to the ‘stiffness’ of the NH⋯N and Cl⋯Cl interactions and ‘softness’ of other van der Waals contacts. Above 0.1 GPa all crystal directions become compressed. However, up to 1.20 GPa, the crystal remains in the same orthorhombic phase of polar space group Fdd2.