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The structures of three polymorphic forms of 4-hydroxy-3-methoxy-4′-nitro-trans-stilbene (HMONS; C 15 H 13 NO 4 ,  M  r  = 271.27) are reported. Crystal growth experiments of HMONS from different solvents and varying conditions showed the existence of three crystalline phases, red crystals with symmetry of the orthorhombic space group  Pbca , with  a  = 7.811(2) Å,  b  = 13.410(4) Å,  c  = 24.597(5) Å ( 1 ), yellow crystals belonging to the monoclinic space group  C 2/ c  with lattice parameters  a  = 18.788(2) Å,  b  = 6.6945(5) Å,  c  = 21.013(2) Å,  β  = 90.761(6)° ( 2 ), and yellowish-orange crystals with space group symmetry  P 2 1 , and  a  = 6.9302(12) Å,  b  = 13.493(4) Å,  c  = 7.247(2) Å,  β  = 102.08(2)° ( 3 ). The latter exhibits a powder second harmonic generation (SHG) efficiency 70 times as large as that of urea.

Crystal structures of three polymorphic forms of 4-hydroxy-3-methoxy-4′-nitro-trans-stilbene