organic compounds
2-(2-{[2-(4-Pyridylcarbonyl)hydrazinylidene]methyl}phenoxy)acetic acid
aCollege of Electronic Engineering (Guilin University of Electronic Technology), Guilin 541004, People's Republic of China, and bCollege of Chemical and Biological Engineering (Guilin University of Technology), Guilin 541004, People's Republic of China
*Correspondence e-mail: lisa4.6@163.com
In the title compound, C15H13N3O4, the pyridine and benzene rings are nearly perpendicular [dihedral angle = 84.24 (5)°]. In the 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 et al. (2000; 2007). For related structures, see: Chen et al. (2006); Hu et al. (2006).
as corrosion inhibitors for metals and alloys, see: FoudaExperimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2004); cell 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.
Supporting information
https://doi.org/10.1107/S1600536810017083/rk2197sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017083/rk2197Isup2.hkl
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.
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
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
procedure.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).
For
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).Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).C15H13N3O4 | F(000) = 624 |
Mr = 299.28 | Dx = 1.432 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 4508 reflections |
a = 12.8099 (12) Å | θ = 3.2–27.8° |
b = 4.9435 (5) Å | µ = 0.11 mm−1 |
c = 21.921 (2) Å | T = 296 K |
V = 1388.2 (2) Å3 | Block, yellow |
Z = 4 | 0.49 × 0.21 × 0.18 mm |
Bruker APEXII CCD diffractometer | 3189 independent reflections |
Radiation source: fine-focus sealed tube | 2891 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −15→16 |
Tmin = 0.950, Tmax = 0.981 | k = −6→6 |
11436 measured reflections | l = −28→28 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.024P)2 + 0.395P] where P = (Fo2 + 2Fc2)/3 |
3189 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
C15H13N3O4 | V = 1388.2 (2) Å3 |
Mr = 299.28 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 12.8099 (12) Å | µ = 0.11 mm−1 |
b = 4.9435 (5) Å | T = 296 K |
c = 21.921 (2) Å | 0.49 × 0.21 × 0.18 mm |
Bruker APEXII CCD diffractometer | 3189 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2891 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.981 | Rint = 0.023 |
11436 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 1 restraint |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.17 e Å−3 |
3189 reflections | Δρmin = −0.16 e Å−3 |
200 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.40315 (13) | −0.2335 (4) | 0.17829 (9) | 0.0418 (4) | |
H1 | 0.4671 | −0.3216 | 0.1815 | 0.050* | |
C2 | 0.32247 (13) | −0.3168 (4) | 0.21532 (8) | 0.0367 (4) | |
H2 | 0.3320 | −0.4593 | 0.2424 | 0.044* | |
C3 | 0.22713 (13) | −0.1862 (3) | 0.21176 (7) | 0.0296 (3) | |
C4 | 0.21671 (14) | 0.0228 (3) | 0.16999 (7) | 0.0362 (4) | |
H4 | 0.1539 | 0.1154 | 0.1661 | 0.043* | |
C5 | 0.30128 (15) | 0.0903 (4) | 0.13447 (8) | 0.0435 (4) | |
H5 | 0.2935 | 0.2295 | 0.1063 | 0.052* | |
C6 | 0.13817 (12) | −0.2813 (3) | 0.25116 (7) | 0.0301 (3) | |
C7 | −0.04427 (13) | 0.0500 (3) | 0.33975 (7) | 0.0315 (3) | |
H7 | −0.0125 | 0.2188 | 0.3371 | 0.038* | |
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 | −0.2925 | 0.3319 | 0.047* | |
C10 | −0.29905 (14) | −0.2103 (4) | 0.40121 (9) | 0.0424 (4) | |
H10 | −0.3485 | −0.3415 | 0.3917 | 0.051* | |
C11 | −0.31293 (13) | −0.0451 (4) | 0.45126 (9) | 0.0452 (5) | |
H11 | −0.3725 | −0.0636 | 0.4752 | 0.054* | |
C12 | −0.23880 (15) | 0.1482 (4) | 0.46622 (8) | 0.0405 (4) | |
H12 | −0.2483 | 0.2577 | 0.5003 | 0.049* | |
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 | −0.1499 | 0.6013 | 0.4946 | 0.050* | |
H14B | −0.0312 | 0.6739 | 0.4897 | 0.050* | |
C15 | −0.06001 (13) | 0.3840 (3) | 0.55373 (8) | 0.0356 (4) | |
N1 | 0.39396 (12) | −0.0327 (3) | 0.13816 (7) | 0.0420 (3) | |
N2 | 0.07678 (10) | −0.0839 (3) | 0.27315 (6) | 0.0330 (3) | |
H2A | 0.0898 | 0.0824 | 0.2645 | 0.040* | |
N3 | −0.00745 (11) | −0.1488 (3) | 0.30979 (6) | 0.0340 (3) | |
O1 | 0.12591 (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) | |
H4A | 0.0110 | 0.1059 | 0.5820 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0328 (9) | 0.0503 (10) | 0.0421 (10) | 0.0020 (8) | 0.0033 (8) | 0.0005 (9) |
C2 | 0.0386 (9) | 0.0369 (9) | 0.0346 (8) | 0.0012 (7) | 0.0031 (7) | 0.0057 (7) |
C3 | 0.0344 (8) | 0.0269 (7) | 0.0275 (7) | −0.0027 (6) | 0.0038 (6) | −0.0025 (6) |
C4 | 0.0378 (9) | 0.0334 (8) | 0.0373 (9) | 0.0048 (7) | 0.0067 (7) | 0.0048 (7) |
C5 | 0.0541 (11) | 0.0383 (9) | 0.0381 (9) | −0.0008 (8) | 0.0103 (9) | 0.0073 (8) |
C6 | 0.0323 (8) | 0.0278 (8) | 0.0301 (8) | −0.0019 (7) | 0.0026 (7) | 0.0007 (6) |
C7 | 0.0332 (9) | 0.0333 (8) | 0.0280 (8) | −0.0021 (7) | −0.0003 (7) | 0.0008 (7) |
C8 | 0.0277 (8) | 0.0350 (8) | 0.0268 (7) | 0.0037 (6) | −0.0011 (6) | 0.0026 (7) |
C9 | 0.0353 (9) | 0.0464 (10) | 0.0351 (9) | −0.0022 (8) | −0.0037 (7) | −0.0041 (8) |
C10 | 0.0281 (8) | 0.0508 (11) | 0.0481 (10) | −0.0051 (8) | −0.0035 (8) | 0.0056 (9) |
C11 | 0.0283 (8) | 0.0622 (12) | 0.0451 (10) | 0.0024 (8) | 0.0101 (8) | 0.0113 (9) |
C12 | 0.0399 (10) | 0.0475 (10) | 0.0340 (8) | 0.0093 (8) | 0.0064 (8) | −0.0011 (8) |
C13 | 0.0325 (8) | 0.0323 (8) | 0.0279 (8) | 0.0052 (7) | −0.0015 (6) | 0.0040 (7) |
C14 | 0.0523 (11) | 0.0339 (9) | 0.0393 (9) | 0.0047 (8) | −0.0032 (8) | −0.0066 (8) |
C15 | 0.0337 (8) | 0.0383 (8) | 0.0348 (8) | −0.0010 (7) | −0.0024 (7) | −0.0064 (8) |
N1 | 0.0413 (8) | 0.0468 (9) | 0.0380 (8) | −0.0091 (7) | 0.0111 (7) | 0.0012 (8) |
N2 | 0.0370 (7) | 0.0245 (6) | 0.0374 (7) | −0.0034 (6) | 0.0110 (6) | 0.0001 (6) |
N3 | 0.0345 (7) | 0.0330 (7) | 0.0344 (7) | −0.0016 (6) | 0.0085 (6) | 0.0017 (6) |
O1 | 0.0527 (7) | 0.0247 (6) | 0.0571 (7) | −0.0024 (5) | 0.0169 (6) | 0.0047 (6) |
O2 | 0.0426 (7) | 0.0373 (6) | 0.0304 (6) | −0.0024 (5) | 0.0009 (5) | −0.0027 (5) |
O3 | 0.0763 (10) | 0.0575 (9) | 0.0378 (7) | 0.0115 (8) | 0.0043 (7) | −0.0142 (7) |
O4 | 0.0540 (8) | 0.0562 (8) | 0.0331 (6) | 0.0224 (6) | −0.0052 (6) | −0.0021 (6) |
C1—N1 | 1.332 (2) | C9—C10 | 1.368 (2) |
C1—C2 | 1.377 (2) | C9—H9 | 0.9300 |
C1—H1 | 0.9300 | C10—C11 | 1.379 (3) |
C2—C3 | 1.384 (2) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C11—C12 | 1.387 (3) |
C3—C4 | 1.387 (2) | C11—H11 | 0.9300 |
C3—C6 | 1.505 (2) | C12—C13 | 1.388 (2) |
C4—C5 | 1.375 (3) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—O2 | 1.3699 (19) |
C5—N1 | 1.336 (2) | C14—O2 | 1.421 (2) |
C5—H5 | 0.9300 | C14—C15 | 1.511 (3) |
C6—O1 | 1.2226 (19) | C14—H14A | 0.9700 |
C6—N2 | 1.343 (2) | C14—H14B | 0.9700 |
C7—N3 | 1.273 (2) | C15—O3 | 1.201 (2) |
C7—C8 | 1.468 (2) | C15—O4 | 1.309 (2) |
C7—H7 | 0.9300 | N2—N3 | 1.3828 (18) |
C8—C9 | 1.391 (2) | N2—H2A | 0.8600 |
C8—C13 | 1.405 (2) | O4—H4A | 0.8200 |
N1—C1—C2 | 123.09 (16) | C9—C10—H10 | 120.1 |
N1—C1—H1 | 118.5 | C11—C10—H10 | 120.1 |
C2—C1—H1 | 118.5 | C10—C11—C12 | 120.53 (16) |
C1—C2—C3 | 119.32 (16) | C10—C11—H11 | 119.7 |
C1—C2—H2 | 120.3 | C12—C11—H11 | 119.7 |
C3—C2—H2 | 120.3 | C13—C12—C11 | 119.79 (16) |
C2—C3—C4 | 118.02 (15) | C13—C12—H12 | 120.1 |
C2—C3—C6 | 119.35 (14) | C11—C12—H12 | 120.1 |
C4—C3—C6 | 122.59 (15) | O2—C13—C12 | 124.86 (15) |
C5—C4—C3 | 118.59 (17) | O2—C13—C8 | 115.15 (13) |
C5—C4—H4 | 120.7 | C12—C13—C8 | 119.98 (15) |
C3—C4—H4 | 120.7 | O2—C14—C15 | 114.78 (14) |
N1—C5—C4 | 123.72 (17) | O2—C14—H14A | 108.6 |
N1—C5—H5 | 118.1 | C15—C14—H14A | 108.6 |
C4—C5—H5 | 118.1 | O2—C14—H14B | 108.6 |
O1—C6—N2 | 123.98 (15) | C15—C14—H14B | 108.6 |
O1—C6—C3 | 121.04 (14) | H14A—C14—H14B | 107.5 |
N2—C6—C3 | 114.97 (13) | O3—C15—O4 | 125.00 (18) |
N3—C7—C8 | 120.21 (14) | O3—C15—C14 | 120.95 (16) |
N3—C7—H7 | 119.9 | O4—C15—C14 | 113.99 (15) |
C8—C7—H7 | 119.9 | C1—N1—C5 | 117.24 (15) |
C9—C8—C13 | 118.44 (15) | C6—N2—N3 | 119.78 (13) |
C9—C8—C7 | 121.77 (15) | C6—N2—H2A | 120.1 |
C13—C8—C7 | 119.79 (14) | N3—N2—H2A | 120.1 |
C10—C9—C8 | 121.54 (17) | C7—N3—N2 | 114.18 (13) |
C10—C9—H9 | 119.2 | C13—O2—C14 | 117.50 (14) |
C8—C9—H9 | 119.2 | C15—O4—H4A | 109.5 |
C9—C10—C11 | 119.70 (17) | ||
N1—C1—C2—C3 | −0.7 (3) | C11—C12—C13—O2 | −178.35 (16) |
C1—C2—C3—C4 | 0.8 (2) | C11—C12—C13—C8 | 0.5 (2) |
C1—C2—C3—C6 | 178.57 (15) | C9—C8—C13—O2 | 177.56 (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—C12 | 178.62 (15) |
C2—C3—C6—O1 | −36.1 (2) | O2—C14—C15—O3 | −164.70 (17) |
C4—C3—C6—O1 | 141.58 (18) | O2—C14—C15—O4 | 17.9 (2) |
C2—C3—C6—N2 | 142.74 (15) | C2—C1—N1—C5 | −0.1 (3) |
C4—C3—C6—N2 | −39.6 (2) | C4—C5—N1—C1 | 0.8 (3) |
N3—C7—C8—C9 | −28.5 (2) | O1—C6—N2—N3 | −1.4 (3) |
N3—C7—C8—C13 | 151.42 (15) | C3—C6—N2—N3 | 179.86 (13) |
C13—C8—C9—C10 | 1.2 (3) | C8—C7—N3—N2 | 177.30 (14) |
C7—C8—C9—C10 | −178.87 (17) | C6—N2—N3—C7 | 163.73 (15) |
C8—C9—C10—C11 | 0.0 (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—C13 | 0.7 (3) | C15—C14—O2—C13 | 74.9 (2) |
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···O3iv | 0.93 | 2.58 | 3.315 (2) | 136 |
C11—H11···O4v | 0.93 | 2.43 | 3.347 (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. |
Experimental details
Crystal data | |
Chemical formula | C15H13N3O4 |
Mr | 299.28 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 296 |
a, b, c (Å) | 12.8099 (12), 4.9435 (5), 21.921 (2) |
V (Å3) | 1388.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.49 × 0.21 × 0.18 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.950, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11436, 3189, 2891 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.071, 1.02 |
No. of reflections | 3189 |
No. of parameters | 200 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.8600 | 2.0100 | 2.8599 (18) | 168.00 |
O4—H4A···N1ii | 0.8200 | 1.8600 | 2.6337 (19) | 156.4 |
C1—H1···O3iii | 0.9300 | 2.5100 | 3.199 (2) | 131.00 |
C4—H4···O3iv | 0.9300 | 2.5800 | 3.315 (2) | 136.00 |
C11—H11···O4v | 0.9300 | 2.4300 | 3.347 (2) | 171.00 |
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. |
Acknowledgements
We acknowledge financial support by the Key Laboratory of Non-Ferrous Metals and Materials Processing Technology, Ministry of Education, China.
References
Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, S.-S., Zhang, S.-P., Huang, C.-B. & Shao, S.-C. (2006). Acta Cryst. E62, o31–o32. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fouda, A. S., Gouda, M. M. & Abd El-Rahman, S. I. (2000). Bull. Korean Chem. Soc. 21, 1085–1089. CAS Google Scholar
Fouda, A. S., Mostafa, S. E., Ghazy, S. E. & El-Farah, S. A. (2007). J. Electrochem. Sci. 2, 182–193. CAS Google Scholar
Hu, R.-H., Fang, X.-N., Sui, Y., Luo, Q.-Y. & Zou, M.-Q. (2006). Acta Cryst. E62, o3558–o3560. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).