Zwitterionic (E)-1-[(4-nitro­phen­yl)iminio­meth­yl]naphthalen-2-olate

Maamar Damous; Meriem Hamlaoui; Sofiane Bouacida; Hocine Merazig; Jean-Claude Daran

doi:10.1107/S1600536811012359

. 2011 Apr 13;67(Pt 5):o1123–o1124. doi: 10.1107/S1600536811012359

Zwitterionic (E)-1-[(4-nitrophenyl)iminiomethyl]naphthalen-2-olate

Maamar Damous ^a, Meriem Hamlaoui ^a, Sofiane Bouacida ^a,^b,^*, Hocine Merazig ^a, Jean-Claude Daran ^c

PMCID: PMC3089354 PMID: 21754437

Abstract

The title compound, C₁₇H₁₂N₂O₃, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-nitrobenzenamine. These condense to form the Schiff base, which crystallizes in the zwitterionic form. In the structure, the keto–amino tautomer has a fairly short intramolecular N—H⋯O hydrogen bond between the 2-naphthalenone and amino groups, with electron delocalization. The molecule is essentially planar, with a dihedral angle of 1.96 (3)° between the ring systems. In the crystal, the molecules are linked via intermolecular C—H⋯O hydrogen bonds, forming a layer parallel to (101).

Related literature

For background to Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For the pharmaceutical and medicinal activity of Schiff bases, see: Chen et al. (1997 ▶); Dao et al. (2000 ▶); Ren et al. (2002 ▶); Sriram et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For Schiff bases in coordination chemistry, see: Ali et al. (2008 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For related structures, see: Fun et al. (2009 ▶); Nadeem et al. (2009 ▶); Eltayeb et al. (2008 ▶). For standard bond lengths see: Allen, (2002 ▶).

Experimental

Crystal data

C₁₇H₁₂N₂O₃
M _r = 292.29
Monoclinic,
a = 8.0503 (6) Å
b = 12.8174 (9) Å
c = 13.1833 (10) Å
β = 97.271 (5)°
V = 1349.37 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.15 × 0.06 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
44074 measured reflections
7946 independent reflections
3658 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.190
S = 0.96
7946 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012359/bq2290sup1.cif

e-67-o1123-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012359/bq2290Isup2.hkl

e-67-o1123-Isup2.hkl^{(380.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	1.09 (2)	1.57 (2)	2.5287 (15)	143 (2)
C5—H5⋯O2ⁱ	0.93	2.59	3.5136 (16)	173
C16—H16⋯O2ⁱ	0.93	2.53	3.4455 (17)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, Algeria and the Laboratoire de Chimie de Coordination, Toulouse, France. Thanks are due to the MESRS (Ministére de l’Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.

supplementary crystallographic information

Comment

Schiff base compounds have been widely investigated over a century (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have pharmaceutical and medicinal fields (Chen et al., 1997; Ren et al., 2002; Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). They are also used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009).

As part of our ongoing studies of Schiff base complexes and derivatives we report here synthesis and the crystal structure of the title compound, obtained by the reaction of 2-hydroxy-1-naphthaldehyde with 4-nitroaniline, which crystallized in a zwitterionic form with cationic iminium and anionic naphtholate group.

The molecular structure of (I), and the atomic numbering used, is illustrated in Fig. 1. All bond distances and angles are within the ranges of accepted values (CSD, Allen, 2002) and in literature (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008).

The main molecule is essentially planar with an rms deviation of 0.0350 Å, and the crystal structure exhibit alternating layers parallel to (101) plane (Fig. 2). In the crystal, molecules are linked via intermolecular C—H···O hydrogen bonds to form a two-dimensional layers parallel to (101) (Table 1, Fig. 3) and additional stabilization within these layers is provided by N—O···π and π···π stacking interactions. These interaction bonds link the molecules within the layers and also link the layers together and reinforcing the cohesion of the structure. An intramolecular N—H···O hydrogen bond occurs.

Experimental

The title compound, (I), was prepared by refluxing a mixture of a solution containing (0.1 mmol) of 2-hydroxy-1-naphthaldehyde and (0.1 mmol) of 4-nitrobenzenamine in 20 ml methanol. The reaction mixture was stirred for 1 h under reflux. Microcrystals of (I) were obtained by allowing the clear solution to stand overnight. The powder product was dissolved and recrystallized from DMSO solution. Some red crystals were carefully isolated under polarizing microscope for analysis by x-ray diffraction.