(E)-4-Chloro-2-{[4-(di­methyl­amino)­benzyl­idene]amino}­phenol

Nadir Ghichi; Mohamed Amine Benaouida; Ali Benosmane; Ali Benboudiaf; Hocine Merazig

doi:10.1107/S1600536814008873

. 2014 Apr 26;70(Pt 5):o603. doi: 10.1107/S1600536814008873

(E)-4-Chloro-2-{[4-(dimethylamino)benzylidene]amino}phenol

Nadir Ghichi ^a, Mohamed Amine Benaouida ^a, Ali Benosmane ^a,^*, Ali Benboudiaf ^a, Hocine Merazig ^a

PMCID: PMC4011262 PMID: 24860397

Abstract

In the title aromatic Schiff base compound, C₁₅H₁₅ClN₂O, the molecule exists in a trans conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 14.49 (6)°. In the crystal, weak C—H⋯π interactions link molecules into supramolecular chains propagated along the a-axis direction.

Related literature

For the use of Schiff bases in synthesis, see: Arora et al. (2002 ▶). For their use as biological, analytical, polymer and liquid crystalline materials, see: Tanaka & Shiraishi (2000 ▶). Schiff bases have been reported to show antibacterial (Jarrahpour & Khalili, 2006 ▶; Jarrahpour et al., 2004 ▶; El-masry et al., 2000 ▶), antifungal (More et al., 2001 ▶; Singh & Dash, 1988 ▶), anticancer (Desai et al., 2001 ▶; Phatak et al., 2000 ▶) and herbicidal activity (Samadhiya & Halve, 2001 ▶). For related structures, see: Akkurt et al. (2005 ▶, 2008 ▶).

Experimental

Crystal data

C₁₅H₁₅ClN₂O
M _r = 274.74
Orthorhombic,
a = 7.411 (5) Å
b = 12.314 (5) Å
c = 29.684 (5) Å
V = 2709 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.03 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer
14319 measured reflections
2346 independent reflections
1895 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.102
S = 1.10
2346 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814008873/xu5785sup1.cif

e-70-0o603-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008873/xu5785Isup2.hkl

e-70-0o603-Isup2.hkl^{(113KB, hkl)}

Click here for additional data file.^{(5.3KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814008873/xu5785Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg2ⁱ	0.93	2.70	3.533 (3)	150
C15—H15B⋯Cg1ⁱⁱ	0.96	2.76	3.581 (4)	142

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance. The authors thank the MESRS (Algeria) for financial support.

supplementary crystallographic information

1. Comment

Schiff bases are widely used for synthetic purposes both by organic and inorganic chemists (Arora et al., 2002) and have uses as biological, analytical, polymer and liquid crystalline materials (Tanaka & Shiraishi, 2000). Schiff bases are reported to show a variety of biological activities such as antibacterial (Jarrahpour & Khalili, 2006; Jarrahpour et al., 2004; El-masry et al., 2000), antifungal (More et al., 2001; Singh & Dash, 1988), anticancer (Desai et al., 2001; Phatak et al., 2000) and herbicidal activities (Samadhiya & Halve, 2001). As an extension of our work on Schiff bases, we report here the crystal structure of the title compound (I).

2. Experimental

A mixture of 3,4-dimethoxyaniline (1 mmol) and 4-nitrobenzaldehyde (1 mmol) was added and heated to form a clear solution. To this a few drops of conc. H2SO4 was added as a catalyst and refluxed for 6 h. After cooling the solution, After stirring at 80°C for 20 min the formed precipitate was filtered off and washed with ice ethanol to give pure Schiff base as an yellow solid in an 80% yield. The crude product was dissolved in ethanol and two spoons of activated charcoal were added. The mixture was filtered over celite® and the product was crystallized from ethyl acetate, yellow crystal was obtained after two weeks.