4-Amino-5-(2-hydroxy­benzyl­idene­amino)benzene-1,2-dicarbonitrile

Yan Cheng; Jing Gao

doi:10.1107/S160053680901157X

. 2009 Apr 8;65(Pt 5):o963. doi: 10.1107/S160053680901157X

4-Amino-5-(2-hydroxybenzylideneamino)benzene-1,2-dicarbonitrile

Yan Cheng ^a, Jing Gao ^a,^*

PMCID: PMC2977663 PMID: 21584006

Abstract

A new tetradentate unsymmetrical Schiff base, C₁₅H₁₀N₄O, has been synthesized from 4,5-dicyano-o-phenylenediamine and o-vanillin in refluxing ethanol. The dihedral angle between the two benzene rings is 39.0 (1)°. There are intramolecular O—H⋯N and weak intermolecular N—H⋯O and N—H⋯N interactions.

Related literature

For the biological activity of Schiff bases, see: Boskovic et al. (2003 ▶); Koizumi et al. (2005 ▶); Oshiob et al. (2005 ▶). For related structures, see: Kannappan et al. (2005 ▶); Zhang et al. (2003 ▶).

Experimental

Crystal data

C₁₅H₁₀N₄O
M _r = 262.27
Monoclinic,
a = 14.0158 (15) Å
b = 12.3650 (13) Å
c = 7.3557 (8) Å
β = 99.904 (2)°
V = 1255.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.989, T _max = 0.993
7234 measured reflections
2838 independent reflections
1770 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.170
S = 1.00
2838 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901157X/fl2237sup1.cif

e-65-0o963-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901157X/fl2237Isup2.hkl

e-65-0o963-Isup2.hkl^{(139.3KB, 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
N3—H1B⋯N2ⁱ	0.930 (18)	2.205 (17)	3.126 (3)	171 (2)
N3—H1C⋯O1ⁱⁱ	0.930 (19)	2.69 (2)	3.206 (3)	115.5 (17)
O1—H1A⋯N4	0.82	1.91	2.639 (2)	147

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

Acknowledgments

The authors acknowledge financial support from Mudanjiang Medical University.

supplementary crystallographic information

Comment

During the past decades, Schiff bases have been intensively investigated not only because of their strong coordination capability but also due to their diverse biological activities, such as antibacterial, antitumor, etc. (Koizumi et al., 2005; Boskovic et al., 2003; Oshiob et al., 2005). The halide groups in schiff base ligands could effectively optimize the properties of the coordination complexes.

X-ray diffraction analysis indicates that (I) is an unsymmetrical Schiff base ligand (fig. 1). The imide bond length 1.283 (2)(2) Å for C(1)–N(4) is slightly longer than that of 4-Bromo-2-(2-pyridylmethyliminomethyl)phenol (1.269 (4) Å) (Zhang et al., 2003). It is noteworthy that there exists relatively weak intermolecular interactions involving the NH moieties and one intramolecular interaction with OH as the donor (Table 1), which are similar to those of its derivative 4-Bromo-2-(2-pyridylmethyliminomethyl)phenol (Zhang et al., 2003).

Experimental

(I) was prepared according to the method reported in the literature (Kannappan et al., 2005). 4,5-dicyano-o-phenylenediamine (2.16 g, 0.02 mol) was added to a stirred ethanol solution of O-vanillin (3.04 g, 0.02 mol (10 ml). The reaction mixture was stirred about 3 h and then the mixture was allowed to stand at room temperature for about two days. Yellow cystals suitable for X-ray diffraction analysis were then collected with a yield of 60%.