N-[(2-Hydroxy-1-naphthyl)(3-nitrophenyl)methyl]acetamide

The title compound, C19H16N2O4, is of interest as a precursor to biologically active substituted quinolines and related compounds. The dihedral angle between the naphthalene ring system and the benzene ring is 81.9 (1)°. The crystal structure is stabilized by N—H⋯O intermolecular hydrogen bonds, linking the molecules into pairs around a center of symmetry. The crystal structure is further stabilized by intermolecular O—H⋯O hydrogen bonds, which link the molecules into chains running along a axis. An intramolecular C—H⋯O short contact is also present.

The title compound, C 19 H 16 N 2 O 4 , is of interest as a precursor to biologically active substituted quinolines and related compounds. The dihedral angle between the naphthalene ring system and the benzene ring is 81.9 (1) . The crystal structure is stabilized by N-HÁ Á ÁO intermolecular hydrogen bonds, linking the molecules into pairs around a center of symmetry. The crystal structure is further stabilized by intermolecular O-HÁ Á ÁO hydrogen bonds, which link the molecules into chains running along a axis. An intramolecular C-HÁ Á ÁO short contact is also present.

N-[(2-Hydroxy-1-naphthyl)(3-nitrophenyl)methyl]acetamide
M. NizamMohideen, A. SubbiahPandi, N. Panneer Selvam and P. T. Perumal Comment N-(substituted phenyl)acetamides are well known for their importance as intermediates in organic synthesis. They are used as precursors for the synthesis of many hetrocyclic compounds (Wen et al., 2005(Wen et al., , 2006. Multi-component reactions (MCRs) have attracted considerable attention in terms of the saving of both energy and raw materials (Devi & Bhuyan, 2004). They have merits over multi-step reactions in several aspects, including the simplicity of a one-pot procedure, possible structural variations and in building up complex molecules (Domling & Ugi, 2000). Much attention has been focused on amide-type compounds and their metal ion complexes for their properties and potential applications including molecular recognition, ion electrodes, photochemistry and topological structures in ion extraction, biochemistry, catalysis and magnetism (Saravanakumar et al., 2005;Yin et al., 2004). The amide linkage [-NHC(O)-] is known to be strong enough to form and maintain protein architectures and has been utilized to create various molecular devices for a spectrum of purposes in organic chemistry.
In order to obtain fundamental information about this phenomenon, an X-ray crystal structure analysis of (I) was undertaken.
The conformation of (I), together with the atom-numbering scheme, is shown in Fig. 1. In the structure, all bond lengths and angles are within normal ranges (Allen et al., 1987), and comparable with those in previously reported structure (Mosslemin et al., 2007). The bond distance of C18=O4 is 1.222 (2) Å, which is typical for double bonds (Liu & Li., 2004). The nitro group is slighty twisted out of the plane of the benzene ring, as indicated by O2-N2-C16-C15 and O3-N2-C16-C15 torsion angles of -162.9 (2) and 14.4 (3)°, respectively, and comparable with those in previously reported structure (Zia-ur-Rehman et al., 2008).
The naphthalene ring is planar, the maximum deviation from the least squares plane being -0.027 (1) Å for atom C7.
Atom O1 deviating by 0.05 (1) Å from the least squares plane of the naphthalene ring. The dihedral angle between the naphthalene and benzene ring is 81.9 (1)°. The dihedral angle between the fused rings is 1.1 (1)°.
The crystal structure is stabilized by N-H···O intermolecular hydrogen bonds (Table 1, Fig 2.) that generate centrosymmetric hydrogenbonded dimers with a cyclic R 2 2 (16) ring system (Bernstein, et al., 1995). The crystal structure is further stabilized by intermolecular O-H···O hydrogen bonds link the molecules into chains running along a axis.

Experimental
A mixture of 3-nitrobenzaldehyde (10 mmol), β-naphthol (10 mmol) and iodine (0.4 mmol, 4 mol%) were mixed in acetonitrile (5 ml). To that suspension acetyl chloride (2.8 mmol, 0.2 ml) was added and the reaction mixture was stirred at room temperature for 3 h. After the completion of the reaction (as monitored by TLC), saturated sodium thiosulfate solution (5 ml) was added. The precipitated solid was filtered and dried. The dried sample was washed with diethyl ether (2 x 10 ml) and again dried. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution in Ethanol.  Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level.