2-(2-{[2-(4-Pyridylcarbon­yl)hydrazinyl­idene]meth­yl}phen­oxy)acetic acid

Jin Hong Xia; Bao Yu Liu; Zheng Liu

doi:10.1107/S1600536810017083

. 2010 May 15;66(Pt 6):o1341. doi: 10.1107/S1600536810017083

2-(2-{[2-(4-Pyridylcarbonyl)hydrazinylidene]methyl}phenoxy)acetic acid

Jin Hong Xia ^a, Bao Yu Liu ^b,^*, Zheng Liu ^b

PMCID: PMC2979532 PMID: 21579430

Abstract

In the title compound, C₁₅H₁₃N₃O₄, the pyridine and benzene rings are nearly perpendicular [dihedral angle = 84.24 (5)°]. In the crystal structure, classical O—H⋯N hydrogen bonding between the OH group of the carboxyl unit and a neighbouring pyridine ring N atom and N—H⋯O hydrogen bonding between the imine NH group and a neighbouring O atom of an acyl unit, together with complementary non-classical C—H⋯O hydrogen bonds between carboxyl O atoms and neighbouring CH groups, link the molecules into a three-dimensional system.

Related literature

For hydrazones as corrosion inhibitors for metals and alloys, see: Fouda et al. (2000 ▶; 2007 ▶). For related structures, see: Chen et al. (2006 ▶); Hu et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M _r = 299.28
Orthorhombic,
a = 12.8099 (12) Å
b = 4.9435 (5) Å
c = 21.921 (2) Å
V = 1388.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.49 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.950, T _max = 0.981
11436 measured reflections
3189 independent reflections
2891 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.071
S = 1.02
3189 reflections
200 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 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/S1600536810017083/rk2197sup1.cif

e-66-o1341-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017083/rk2197Isup2.hkl

e-66-o1341-Isup2.hkl^{(156.5KB, 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
N2—H2A⋯O1ⁱ	0.86	2.01	2.8599 (18)	168
O4—H4A⋯N1ⁱⁱ	0.82	1.86	2.6337 (19)	156
C1—H1⋯O3ⁱⁱⁱ	0.93	2.51	3.199 (2)	131
C4—H4⋯O3^iv	0.93	2.58	3.315 (2)	136
C11—H11⋯O4^v	0.93	2.43	3.347 (2)	171

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

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

supplementary crystallographic information

Comment

The hydrazone compounds have a strong ability of coordination, which have been investigated as corrosion inhibitors for metals and their alloys (Fouda et al., 2000; 2007). The title compound (Fig.1) is closely related to the previously reported (E)-2-[2-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4- yliminomethyl) phenoxy]acetic acid monohydrate (Hu et al., 2006) and 1-(4-Aminophenyl)ethanone isonicotinoylhydrazone (Chen et al., 2006). The molecular structure of title compound reveals the nearly perpendicular system, in which dihedral angle between the pyridine and benzene rings is 84.24 (5)°. Adjacent molecules are connected by intermolecular classical O–H···N, N–H···O and non-classical C–H···O hydrogen bonds (Fig.2).

Experimental

The methanol (10 ml) was added to an acetone solution (10 ml) of the 2-(2-{[2-(4-pyridylcarbonyl)hydrazono]methyl}phen-oxy)acetic acid (0.5 mmol). After stirring at 308 K for 2 h, crystals of the title compound were obtained by slow evaporation of the solution at room temperature.