N 1-[(1H-Imidazol-2-yl)methyl­idene]-N 4-phenyl­benzene-1,4-di­amine

Md Serajul Haque Faizi; Ashraf Mashrai; M Shahid; Musheer Ahmad

doi:10.1107/S1600536814014238

. 2014 Jun 25;70(Pt 7):o806. doi: 10.1107/S1600536814014238

N ¹-[(1H-Imidazol-2-yl)methylidene]-N ⁴-phenylbenzene-1,4-diamine

Md Serajul Haque Faizi ^a, Ashraf Mashrai ^b, M Shahid ^b,^*, Musheer Ahmad ^a

PMCID: PMC4120595 PMID: 25161587

Abstract

The title compound, C₁₆H₁₄N₄, is non-planar with dihedral angles between the planes of the imidazole and phenylenediamine rings of 30.66 (4)° and between the planes of the phenylenediamine and N-phenyl rings of 56.63 (7)°. In the crystal, molecules are connected by N—H⋯N hydrogen bonds, generating a chain extending along the b-axis direction. The crystal structure is also stabilized by C—H⋯π interactions between N-phenyl and imidazole rings and slipped π–π stacking interactions between imidazole rings [centroid–centroid distance = 3.516 (4) Å] giving an overall two-dimensional layered structure lying parallel to (010).

Keywords: crystal structure

Related literature

For applications of Schiff bases, see: Lozier et al. (1975 ▶); Dalapati et al. (2011 ▶); Sun et al. (2012 ▶). The present work is part of an ongoing structural study of Schiff base–metal complexes, see: Faizi & Hussain (2014 ▶); Faizi & Sen (2014 ▶). For related Schiff bases and their applications, see: Thompson et al. (2012 ▶); Shue et al. (1994 ▶); Garcia et al. (2006 ▶). graphic file with name e-70-0o806-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₄N₄
M _r = 262.31
Monoclinic,
a = 15.663 (5) Å
b = 5.063 (3) Å
c = 16.800 (5) Å
β = 93.124 (5)°
V = 1330.3 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.984, T _max = 0.990
11186 measured reflections
3296 independent reflections
2403 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.110
S = 1.03
3296 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814014238/gg2140sup1.cif

e-70-0o806-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014238/gg2140Isup2.hkl

e-70-0o806-Isup2.hkl^{(158.4KB, hkl)}

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

Supporting information file. DOI: 10.1107/S1600536814014238/gg2140Isup3.cml

CCDC reference: 1008808

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

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

Cg1 is the centroid of the N3/N4/C14–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H101⋯N3ⁱ	0.86	2.09	2.875 (3)	151
C2—H2⋯Cg1ⁱⁱ	0.93	2.83	3.691 (3)	155

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

Acknowledgments

The authors are grateful to the Department of Chemistry, Aligarh Muslim University, India, and SERB–DST, New Delhi, for financial assistance (Ref SR/FT/CS-76/2011).

supplementary crystallographic information

S1. Comment

Schiff bases often exhibit various biological activities and in many cases were shown to have antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al., 1975). They are used as anion sensors (Dalapati et al., 2011) and as non-linear optics compounds (Sun et al., 2012). The present work is part of an ongoing structural study of Schiff base metal complexes (Faizi & Hussain, 2014; Faizi & Sen, 2014) and we report here the structure of N1-((1H-imidazol-2-yl)methylene)-N4-phenylbenzene-1,4-diamine (IMPD). There are very few examples similar to title compound and their metal complex have been reported in the literature (Thompson et al., 2012; Shue et al., 1994; Garcia et al., 2006). The synthesis of IMPD by condensation of 2-imidazolecarboxaldehyde and N-phenyl-p-phenylenediamine has not previously been reported. In the title compound (Fig. 1) IMPD has non planar structure, the dihedral angle between the imidazole and phenylenediamine rings is 30.66 (4) ° and the dihedral angle between the phenylenediamine and N-phenyl rings is 56.63 (7) °. The imine group displays a torsional angle (C10—N2—C13—C14) of 177.29 (2)°. In the crystal, molecules are connected by intermolecular N—H···N hydrogen bond interaction generate a one-dimensional chain structure extending along c axis (Table 1, Fig 2). The crystal structure is also stabilized by C—H···π interations between N-phenyl and imidazole and slipped π–π stacking interactions between imidazole rings [centroid–centroid distance = 3.516 (4) Å] give an overall two-dimensional layered structure lying parallel to (010) given in Fig 3.

S2. Experimental

100 mg (1 mmol) of N-phenyl-p-phenylenediamine were dissolved in 10 ml of absolute ethanol. To this solution, 52 mg (1 mmol) of 2-imidazolecarboxaldehyde in 5 ml of absolute ethanol was dropwisely added under stirring. Then, this mixture was stirred for 10 min, two drops of glacial acetic acid were then added and the mixture was further refluxed for 2h. The resulting light green precipitate was recovered by filtration, washed several times with a small portions of EtOH and then with diethyl ether to give 120 mg (86%) of N1-((1H-imidazol-2-yl)methylene)-N4-phenylbenzene-1,4-diamine (IMPD). The crystal of the title compound suitable for X-ray analysis was obtained within 3 days by slow evaporation of the MeOH solvent.