Crystal engineering of urea α-network via I⋯O 2 N synthon and design of SHG active crystal N-4-iodophenyl-N′-4′-nitrophenylurea

Crystalline nitrodiphenyl ureas adopt the N-H...O tape alpha-network only when stabilization accrues from the I...O(2)N or C[triple bond]C-H...O(2)N synthon, otherwise the ureanitro motif is preferred; soft, weak interactions can direct polar self-assembly in strong N-HO hydrogen-bonded crystals.