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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1341.
Published online 2010 May 15. doi:  10.1107/S1600536810017083
PMCID: PMC2979532

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

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 [triangle]; 2007 [triangle]). For related structures, see: Chen et al. (2006 [triangle]); Hu et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1341-scheme1.jpg

Experimental

Crystal data

  • C15H13N3O4
  • M r = 299.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1341-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.16 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017083/rk2197sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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.

Refinement

The H atoms were placed in calculated positions (C–H = 0.93Å and 0.97Å, O–H = 0.82Å, N–H = 0.86Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C, N) and Uiso(H) = 1.5Ueq(O).

The 1548 Friedel pairs were merged in structure refinement procedure.

Figures

Fig. 1.
The molecular structure of title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
Fig. 2.
A view of the 3-dimensional system of hydrogen bonds.

Crystal data

C15H13N3O4F(000) = 624
Mr = 299.28Dx = 1.432 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 4508 reflections
a = 12.8099 (12) Åθ = 3.2–27.8°
b = 4.9435 (5) ŵ = 0.11 mm1
c = 21.921 (2) ÅT = 296 K
V = 1388.2 (2) Å3Block, yellow
Z = 40.49 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer3189 independent reflections
Radiation source: fine-focus sealed tube2891 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −15→16
Tmin = 0.950, Tmax = 0.981k = −6→6
11436 measured reflectionsl = −28→28

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.024P)2 + 0.395P] where P = (Fo2 + 2Fc2)/3
3189 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = −0.15 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.40315 (13)−0.2335 (4)0.17829 (9)0.0418 (4)
H10.4671−0.32160.18150.050*
C20.32247 (13)−0.3168 (4)0.21532 (8)0.0367 (4)
H20.3320−0.45930.24240.044*
C30.22713 (13)−0.1862 (3)0.21176 (7)0.0296 (3)
C40.21671 (14)0.0228 (3)0.16999 (7)0.0362 (4)
H40.15390.11540.16610.043*
C50.30128 (15)0.0903 (4)0.13447 (8)0.0435 (4)
H50.29350.22950.10630.052*
C60.13817 (12)−0.2813 (3)0.25116 (7)0.0301 (3)
C7−0.04427 (13)0.0500 (3)0.33975 (7)0.0315 (3)
H7−0.01250.21880.33710.038*
C8−0.13670 (12)0.0137 (3)0.37849 (7)0.0298 (3)
C9−0.21215 (14)−0.1804 (4)0.36554 (8)0.0389 (4)
H9−0.2033−0.29250.33190.047*
C10−0.29905 (14)−0.2103 (4)0.40121 (9)0.0424 (4)
H10−0.3485−0.34150.39170.051*
C11−0.31293 (13)−0.0451 (4)0.45126 (9)0.0452 (5)
H11−0.3725−0.06360.47520.054*
C12−0.23880 (15)0.1482 (4)0.46622 (8)0.0405 (4)
H12−0.24830.25770.50030.049*
C13−0.15039 (13)0.1779 (3)0.43020 (7)0.0309 (3)
C14−0.08010 (16)0.5251 (4)0.49371 (8)0.0418 (4)
H14A−0.14990.60130.49460.050*
H14B−0.03120.67390.48970.050*
C15−0.06001 (13)0.3840 (3)0.55373 (8)0.0356 (4)
N10.39396 (12)−0.0327 (3)0.13816 (7)0.0420 (3)
N20.07678 (10)−0.0839 (3)0.27315 (6)0.0330 (3)
H2A0.08980.08240.26450.040*
N3−0.00745 (11)−0.1488 (3)0.30979 (6)0.0340 (3)
O10.12591 (11)−0.5216 (2)0.26232 (7)0.0448 (3)
O2−0.07106 (9)0.3570 (2)0.44137 (5)0.0368 (3)
O3−0.08545 (13)0.4859 (3)0.60119 (6)0.0572 (4)
O4−0.01015 (11)0.1540 (3)0.54842 (6)0.0478 (3)
H4A0.01100.10590.58200.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0328 (9)0.0503 (10)0.0421 (10)0.0020 (8)0.0033 (8)0.0005 (9)
C20.0386 (9)0.0369 (9)0.0346 (8)0.0012 (7)0.0031 (7)0.0057 (7)
C30.0344 (8)0.0269 (7)0.0275 (7)−0.0027 (6)0.0038 (6)−0.0025 (6)
C40.0378 (9)0.0334 (8)0.0373 (9)0.0048 (7)0.0067 (7)0.0048 (7)
C50.0541 (11)0.0383 (9)0.0381 (9)−0.0008 (8)0.0103 (9)0.0073 (8)
C60.0323 (8)0.0278 (8)0.0301 (8)−0.0019 (7)0.0026 (7)0.0007 (6)
C70.0332 (9)0.0333 (8)0.0280 (8)−0.0021 (7)−0.0003 (7)0.0008 (7)
C80.0277 (8)0.0350 (8)0.0268 (7)0.0037 (6)−0.0011 (6)0.0026 (7)
C90.0353 (9)0.0464 (10)0.0351 (9)−0.0022 (8)−0.0037 (7)−0.0041 (8)
C100.0281 (8)0.0508 (11)0.0481 (10)−0.0051 (8)−0.0035 (8)0.0056 (9)
C110.0283 (8)0.0622 (12)0.0451 (10)0.0024 (8)0.0101 (8)0.0113 (9)
C120.0399 (10)0.0475 (10)0.0340 (8)0.0093 (8)0.0064 (8)−0.0011 (8)
C130.0325 (8)0.0323 (8)0.0279 (8)0.0052 (7)−0.0015 (6)0.0040 (7)
C140.0523 (11)0.0339 (9)0.0393 (9)0.0047 (8)−0.0032 (8)−0.0066 (8)
C150.0337 (8)0.0383 (8)0.0348 (8)−0.0010 (7)−0.0024 (7)−0.0064 (8)
N10.0413 (8)0.0468 (9)0.0380 (8)−0.0091 (7)0.0111 (7)0.0012 (8)
N20.0370 (7)0.0245 (6)0.0374 (7)−0.0034 (6)0.0110 (6)0.0001 (6)
N30.0345 (7)0.0330 (7)0.0344 (7)−0.0016 (6)0.0085 (6)0.0017 (6)
O10.0527 (7)0.0247 (6)0.0571 (7)−0.0024 (5)0.0169 (6)0.0047 (6)
O20.0426 (7)0.0373 (6)0.0304 (6)−0.0024 (5)0.0009 (5)−0.0027 (5)
O30.0763 (10)0.0575 (9)0.0378 (7)0.0115 (8)0.0043 (7)−0.0142 (7)
O40.0540 (8)0.0562 (8)0.0331 (6)0.0224 (6)−0.0052 (6)−0.0021 (6)

Geometric parameters (Å, °)

C1—N11.332 (2)C9—C101.368 (2)
C1—C21.377 (2)C9—H90.9300
C1—H10.9300C10—C111.379 (3)
C2—C31.384 (2)C10—H100.9300
C2—H20.9300C11—C121.387 (3)
C3—C41.387 (2)C11—H110.9300
C3—C61.505 (2)C12—C131.388 (2)
C4—C51.375 (3)C12—H120.9300
C4—H40.9300C13—O21.3699 (19)
C5—N11.336 (2)C14—O21.421 (2)
C5—H50.9300C14—C151.511 (3)
C6—O11.2226 (19)C14—H14A0.9700
C6—N21.343 (2)C14—H14B0.9700
C7—N31.273 (2)C15—O31.201 (2)
C7—C81.468 (2)C15—O41.309 (2)
C7—H70.9300N2—N31.3828 (18)
C8—C91.391 (2)N2—H2A0.8600
C8—C131.405 (2)O4—H4A0.8200
N1—C1—C2123.09 (16)C9—C10—H10120.1
N1—C1—H1118.5C11—C10—H10120.1
C2—C1—H1118.5C10—C11—C12120.53 (16)
C1—C2—C3119.32 (16)C10—C11—H11119.7
C1—C2—H2120.3C12—C11—H11119.7
C3—C2—H2120.3C13—C12—C11119.79 (16)
C2—C3—C4118.02 (15)C13—C12—H12120.1
C2—C3—C6119.35 (14)C11—C12—H12120.1
C4—C3—C6122.59 (15)O2—C13—C12124.86 (15)
C5—C4—C3118.59 (17)O2—C13—C8115.15 (13)
C5—C4—H4120.7C12—C13—C8119.98 (15)
C3—C4—H4120.7O2—C14—C15114.78 (14)
N1—C5—C4123.72 (17)O2—C14—H14A108.6
N1—C5—H5118.1C15—C14—H14A108.6
C4—C5—H5118.1O2—C14—H14B108.6
O1—C6—N2123.98 (15)C15—C14—H14B108.6
O1—C6—C3121.04 (14)H14A—C14—H14B107.5
N2—C6—C3114.97 (13)O3—C15—O4125.00 (18)
N3—C7—C8120.21 (14)O3—C15—C14120.95 (16)
N3—C7—H7119.9O4—C15—C14113.99 (15)
C8—C7—H7119.9C1—N1—C5117.24 (15)
C9—C8—C13118.44 (15)C6—N2—N3119.78 (13)
C9—C8—C7121.77 (15)C6—N2—H2A120.1
C13—C8—C7119.79 (14)N3—N2—H2A120.1
C10—C9—C8121.54 (17)C7—N3—N2114.18 (13)
C10—C9—H9119.2C13—O2—C14117.50 (14)
C8—C9—H9119.2C15—O4—H4A109.5
C9—C10—C11119.70 (17)
N1—C1—C2—C3−0.7 (3)C11—C12—C13—O2−178.35 (16)
C1—C2—C3—C40.8 (2)C11—C12—C13—C80.5 (2)
C1—C2—C3—C6178.57 (15)C9—C8—C13—O2177.56 (14)
C2—C3—C4—C5−0.2 (2)C7—C8—C13—O2−2.4 (2)
C6—C3—C4—C5−177.86 (16)C9—C8—C13—C12−1.4 (2)
C3—C4—C5—N1−0.6 (3)C7—C8—C13—C12178.62 (15)
C2—C3—C6—O1−36.1 (2)O2—C14—C15—O3−164.70 (17)
C4—C3—C6—O1141.58 (18)O2—C14—C15—O417.9 (2)
C2—C3—C6—N2142.74 (15)C2—C1—N1—C5−0.1 (3)
C4—C3—C6—N2−39.6 (2)C4—C5—N1—C10.8 (3)
N3—C7—C8—C9−28.5 (2)O1—C6—N2—N3−1.4 (3)
N3—C7—C8—C13151.42 (15)C3—C6—N2—N3179.86 (13)
C13—C8—C9—C101.2 (3)C8—C7—N3—N2177.30 (14)
C7—C8—C9—C10−178.87 (17)C6—N2—N3—C7163.73 (15)
C8—C9—C10—C110.0 (3)C12—C13—O2—C14−0.1 (2)
C9—C10—C11—C12−1.0 (3)C8—C13—O2—C14−178.99 (14)
C10—C11—C12—C130.7 (3)C15—C14—O2—C1374.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.012.8599 (18)168
O4—H4A···N1ii0.821.862.6337 (19)156
C1—H1···O3iii0.932.513.199 (2)131
C4—H4···O3iv0.932.583.315 (2)136
C11—H11···O4v0.932.433.347 (2)171

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y, z+1/2; (iii) −x+1/2, y−1, z−1/2; (iv) −x, −y+1, z−1/2; (v) x−1/2, −y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2197).

References

  • Bruker (1998). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, S.-S., Zhang, S.-P., Huang, C.-B. & Shao, S.-C. (2006). Acta Cryst. E62, o31–o32.
  • Fouda, A. S., Gouda, M. M. & Abd El-Rahman, S. I. (2000). Bull. Korean Chem. Soc.21, 1085–1089.
  • Fouda, A. S., Mostafa, S. E., Ghazy, S. E. & El-Farah, S. A. (2007). J. Electrochem. Sci.2, 182–193.
  • Hu, R.-H., Fang, X.-N., Sui, Y., Luo, Q.-Y. & Zou, M.-Q. (2006). Acta Cryst. E62, o3558–o3560.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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