Crystal structure of 2-[(2-bromophenylimino)methyl]-4-chlorophenol, C13H9BrClNO

Abstract

C 13 H 9 BrClNO, orthorhombic, Pbca (no. 61), a =7.102(1) Å, b =13.082(2) Å, c =25.333(5) Å, V =2353.6 Å 3 , Z =8,Source of material 5-Chlorosalicylaldehyde(0.5 mmol) and an equimolar quantity of 2-bromoaniline were dissolved in methanol (50 mL). The reaction mixture was stirred at room temperature for 30 min and allowedtostand in air. Yellow crystals were formedafter 5days. They were filtered andw ashedw iths mall amountso fc ooled methanol, and finally recrystallized from methanol in good yield (76.8 %). configuration about the C=N. The whole molecule is nearly coplanar with the dihedral angle between two phenyl rings of 9.59°, which is interpreted by conjugation effect and the stabilization of rings from intramolecular hydrogen bond. In the structure, the bromine atom at the phenyl ring is slightly twisted out of the ring with the torsion angle Br1-C1-C2-C3 =-179.9(1)°and the hydroxylgroup nearly oriented out of the phenyl ring, as indicated by the torsion angle Experimental details