Research Article: (E)-4-Bromo-2-[(2-hydroxy­phen­yl)iminiometh­yl]phenolate

Date Published: June 01, 2010

Publisher: International Union of Crystallography

Author(s): Naser Eltaher Eltayeb, Siang Guan Teoh, Hoong-Kun Fun, Suchada Chantrapromma.


The title compound, C13H10BrNO2, crystallizes in a zwitterionic form. The zwitterion exists in a trans configuration about the C=N bond and is almost planar, the dihedral angle between the two benzene rings being 2.29 (9)°. An intra­molecular N—H⋯O hydrogen bond formed between the iminium NH+ and the phenolate O− atoms generates an S(6) ring motif. In the crystal, the zwitterions are linked through O—H⋯O hydrogen bonds into chains along [101] and these chains are further connected through C—H⋯Br inter­actions into a two-dimensional network perpendicular to (101). C⋯C [3.572 (3)–3.592 (3) Å] and C⋯Br [3.5633 (19)–3.7339 (18) Å] short contacts are observed. The crystal studied was a twin with twin law 00, 00, 001 with a domain ratio of 0.09919 (2):0.90081 (2).

Partial Text

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff bases and their applications, see: Dao et al. (2000 ▶); Kagkelari et al. (2009 ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶); Wei & Atwood (1998 ▶). For related structures, see: Eltayeb et al. (2009 ▶; 2010 ▶); Tan & Liu (2009 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).




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