N-[4-(Phenyl­imino­meth­yl)phen­yl]acetamide 0.67-hydrate

Tariq Mahmud; Khalid H Thebo; Rabia Rehman; Mohammad A Malik; Madeleine Helliwell

doi:10.1107/S1600536810039656

. 2010 Oct 9;66(Pt 11):o2781. doi: 10.1107/S1600536810039656

N-[4-(Phenyliminomethyl)phenyl]acetamide 0.67-hydrate

Tariq Mahmud ^a,^*, Khalid H Thebo ^b, Rabia Rehman ^a, Mohammad A Malik ^b, Madeleine Helliwell ^b

PMCID: PMC3009366 PMID: 21588979

Abstract

The title compound, C₁₅H₁₄N₂O·0.67H₂O, was prepared by the reaction of 4-acetoaminebenzaldehyde and aniline. The asymmetric unit contains six organic molecules and four water molecules. The dihedral angles between the aromatic ring planes in each organic molecule vary from 42.4 (2) to 53.8 (2)°. In the crystal, an extensive network of intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds link the molecules into [010] chains.

Related literature

For background to polydentate Schiff bases in coordination chemistry, see: Souza et al. (1985 ▶); Dixit et al. (2009 ▶). For information on their uses as stereospecific catalysts, see: Kureshy et al. (1999 ▶); Aoyama et al. (1986 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O·0.67H₂O
M _r = 250.29
Monoclinic,
a = 21.328 (4) Å
b = 17.797 (3) Å
c = 23.021 (4) Å
β = 117.244 (4)°
V = 7769 (3) Å³
Z = 24
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.60 × 0.35 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
40121 measured reflections
13696 independent reflections
4483 reflections with I > 2σ(I)
R _int = 0.113

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.119
S = 0.76
13696 reflections
1057 parameters
23 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039656/hb5642sup1.cif

e-66-o2781-sup1.cif^{(50.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039656/hb5642Isup2.hkl

e-66-o2781-Isup2.hkl^{(669.5KB, 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
N1—H1N⋯O1S	0.88 (2)	2.00 (2)	2.872 (5)	173 (4)
N3—H3N⋯O2S	0.87 (2)	1.99 (2)	2.859 (5)	173 (4)
N5—H5N⋯O4S	0.86 (2)	2.09 (2)	2.919 (5)	163 (4)
N7—H7N⋯O3S	0.86 (2)	2.03 (2)	2.858 (5)	161 (4)
N9—H9N⋯O4	0.87 (2)	2.10 (2)	2.929 (5)	158 (4)
N11—H11N⋯O2	0.87 (2)	2.16 (3)	2.947 (5)	151 (4)
O1S—H1O⋯N4	0.83 (2)	2.29 (3)	2.939 (5)	136 (4)
O1S—H2O⋯O5	0.88 (2)	1.88 (2)	2.764 (5)	173 (4)
O2S—H3O⋯N2	0.85 (2)	2.16 (2)	3.006 (5)	177 (4)
O2S—H4O⋯O3	0.86 (2)	1.96 (2)	2.781 (5)	160 (5)
O3S—H5O⋯N6ⁱ	0.85 (2)	2.33 (3)	3.001 (5)	136 (3)
O3S—H6O⋯O1ⁱ	0.89 (2)	1.90 (2)	2.778 (4)	172 (4)
O4S—H7O⋯N8ⁱⁱ	0.87 (2)	2.09 (2)	2.954 (5)	171 (4)
O4S—H8O⋯O6ⁱⁱ	0.98 (2)	1.76 (2)	2.726 (5)	170 (4)

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

Acknowledgments

The authors thank the University of the Punjab and the Higher Education Commission (HEC), Government of Pakistan, for financial support, and are also grateful to the School of Chemistry, The University of Manchester, England, for providing research facilities.

supplementary crystallographic information

Comment

Polydentate Schiff base ligands are widely used in the preparation of transition metal complexes (Souza et al., 1985). Some such complexes possess binding sites and cavities for various cations, anions and organic molecules (Dixit et al., 2009). In addition, Schiff base metal complexes can be effective as stereospecific catalysts for oxidation (Kureshy et al., 1999), reduction (Aoyama et al., 1986) and other transformations in organic and inorganic chemistry. The title Schiff base compound was synthesized from 4-acetoaminebenzaldehyde and aniline as a potential ligand for the preparation of transition metal complexes.

The asymmetric unit contains six molecules of 4-acetylaminobenzylidine aniline (I) and four water molecules. Figure 1 shows a plot of one of the molecules of (I). The dihedral angles between the two aromatic ring planes in each molecule of (I) vary from 42.4 (2) to 53.8 (2)° (Table 2). The six molecules in the asymetric unit are arranged in pairs, one above the other. There are possible π-stacking interactions between the carbonyl group of each molecule in the pair with the central phenyl group of the molecule above or below it, with carbonyl O and C atoms to aromatic ring distances varying from 3.002 (4) to 3.421 (4) Å and 3.191 (6) to 3.492 (6) Å, respectively (Table 3, Figure 2). The paired molecules are further linked to one another by O—H···N and O—H···O hydrogen bonds from two water molecules, one at each side of the pair (Table 1, Figure 2). Each pair of molecules is linked to adjacent pairs on either side by N—H···O contacts (Table 3), either to water O atoms (i.e. the N1—H1···O1S, N3—H3···O2S, N5—H5···O4S and N7—H7···O3S contacts) or to a carbonyl oxygen of the next molecule (i.e. the N11—H11···O2 and the N9—H9···O4 contacts). In this way, the pairs of molecules are linked into chains along b, as shown in Figure 2.

Experimental

0.0163 g (1.0 mmol) of 4-acetoaminebenzaldehyde and 0.0911 ml (1.0 mmol) of aniline were dissolved in 10.0 ml 95% ethanol separately. Both solutions were mixed in 100 ml round bottom flask. The mixture was refluxed for two hours at 423 K. It was then recrystallized by using a mixture of acetonitrile, methanol and water in the ratio 1: 3: 4 respectively.