2-(2-{[2-(2-Pyridylcarbon­yl)hydrazono]meth­yl}phen­oxy)acetic acid

Bao-Yu Liu; Zheng Liu; Guo-Rui Wang

doi:10.1107/S160053680905082X

. 2009 Dec 4;66(Pt 1):o26. doi: 10.1107/S160053680905082X

2-(2-{[2-(2-Pyridylcarbonyl)hydrazono]methyl}phenoxy)acetic acid

Bao-Yu Liu ^a,^*, Zheng Liu ^a, Guo-Rui Wang ^a

PMCID: PMC2980243 PMID: 21580133

Abstract

In the title compound, C₁₅H₁₃N₃O₄, the pyridine and benzene rings are nearly coplanar [dihedral angle = 4.92 (12)°]. The maximum deviation from the best least-squares plane calculated for the main molecular skeleton is 0.1722 (1) Å for the carbonyl O atom. In the crystal, intermolecular O—H⋯O hydrogen bonds connect the molecules into a chain, while π–π stacking interactions between the pyridine and benzene rings [centroid–centroid distance = 3.9162 (8) Å and offset angle = 27.20°] complete a two-dimensional network.

Related literature

For Schiff bases complexes containing (O-oxyacetic acid)benzaldehyde, see: Wu et al. (2003 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M _r = 299.28
Monoclinic,
a = 8.871 (2) Å
b = 9.042 (2) Å
c = 17.389 (4) Å
β = 94.765 (3)°
V = 1390.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.16 × 0.15 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.983, T _max = 0.996
11832 measured reflections
3194 independent reflections
1512 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.125
S = 0.99
3194 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905082X/kp2238sup1.cif

e-66-00o26-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905082X/kp2238Isup2.hkl

e-66-00o26-Isup2.hkl^{(156.7KB, 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
O4—H4A⋯O1ⁱ	0.82	1.83	2.642 (2)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge financial support by the Key Laboratory of Non-ferrous Metals and Materials Processing Technology, Ministry of Education, P. R. China.

supplementary crystallographic information

Comment

The molecular structure of (I) (Fig.1) reveals the nearly planar system; the dihedral angle between the pyridine and benzene rings is 4.923°. An intermolecular O–H···O hydrogen bond connects molecules into a chain (Table 1, Fig.2). The pyridine ring (1-x,-1/2+y,1/2-z) is parallel to the benzene ring (-x,-1/2+y,1/2-z) with a perpendicular distance of 3.3239 Å: a centroid–centroid = 3.9162 (8) Å and an offset angle = 27.197° (calculated as the angle between the line through the two centroids of the pyridine ring and the benzene ring and a normal to the pyridine plane. Thus pi–pi stacking interactions complete a two dimensional network (Fig.2).

Experimental

A methanol solution (10 ml) was added to an acetone solution (10 ml) of the 2-(2-methoxyacetic acid)benzaldehyde picoloylhydrazone (0.5 mmol). After stirring at 35\ % for 2 h, crystals of the title compound were obtained by slow evaporation of the mixture at room temperature.