6-Chloro-1-phenyl-indoline-2,3-dione: absolute structure, non-linear optical and charge-transport properties

In the title compound, C₁₄H₈ClNO₂, the dihedral angle between the isatin moiety (r.m.s. deviation = 0.014 Å) and the phenyl ring is 51.8 (1)°. All mol-ecules have the same 'frozen chiral' conformation in the non-centrosymmetric P2₁2₁2₁ space group. A polycrystalline sample of the title compound exhibits a considerable second-order non-linear optical effect (frequency doubling of 1064 nm light to output 532 nm light). In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, generating chains along the [100] direction. Based on a DFT calculation, [100] proves to be the most favourable direction for charge transport and the title crystal could be used as a hole-transport material because of its high hole mobility.