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

In the title compound, C(14)H(8)ClNO(2), the dihedral angle between the isatin moiety (r.m.s. deviation = 0.014 Å) and the phenyl ring is 51.8 (1)°. All mol­ecules have the same ‘frozen chiral’ conformation in the non-centrosymmetric P2(1)2(1)2(1) 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, mol­ecules 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.