N′-[(E)-4-Hydr­oxy-3-methoxy­benzyl­idene]pyridine-4-carbohydrazide

Zahid Shafiq; Muhammad Yaqub; M Nawaz Tahir; Abid Hussain; M Saeed Iqbal

doi:10.1107/S1600536809044134

. 2009 Oct 28;65(Pt 11):o2899. doi: 10.1107/S1600536809044134

N′-[(E)-4-Hydroxy-3-methoxybenzylidene]pyridine-4-carbohydrazide

Zahid Shafiq ^a, Muhammad Yaqub ^b, M Nawaz Tahir ^c,^*, Abid Hussain ^b, M Saeed Iqbal ^d

PMCID: PMC2971391 PMID: 21578481

Abstract

In the title compound, C₁₄H₁₃N₃O₃, the two six-membered rings are oriented at a dihedral angle of 15.17 (11)° and an intramolecular O—H⋯O hydrogen bond occurs. In the crystal, molecules interact by way of N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, thereby generating S(5) chain and R ₂ ¹(7) ring motifs.

Related literature

For related structures, see: Liu & Shi (2007 ▶); Shi et al. (2007 ▶); Shafiq et al. (2009 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₃N₃O₃
M _r = 271.27
Monoclinic,
a = 14.8543 (10) Å
b = 12.4943 (9) Å
c = 7.7162 (5) Å
β = 116.716 (2)°
V = 1279.20 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.32 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.973, T _max = 0.984
7060 measured reflections
1613 independent reflections
1431 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.086
S = 1.04
1613 reflections
183 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044134/hb5177sup1.cif

e-65-o2899-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044134/hb5177Isup2.hkl

e-65-o2899-Isup2.hkl^{(77.9KB, 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
O2—H2B⋯O3	0.82	2.25	2.694 (2)	114
N2—H2A⋯O1ⁱ	0.86	2.25	3.089 (2)	164
O2—H2B⋯N1ⁱⁱ	0.82	1.96	2.703 (3)	150
C5—H5⋯O1ⁱ	0.93	2.55	3.410 (3)	153

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

Acknowledgments

AH gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 063–121531-PS3–127).

supplementary crystallographic information

Comment

We have reported the crystal structures of (II) N'-[(E)-(4-Hydroxy-3-methoxyphenyl)methylidene]benzohydrazide (Shafiq et al., 2009). The title compound (I, Fig. 1), has been prepared in continuation of synthesizing hydrazide derivatives.

The crystal structure of (III) N'-(4-Hydroxy-3-methoxybenzylidene)isonicotinohydrazide monohydrate (Shi et al., 2007) and (IV) N'-(4-Hydroxy-3-methoxybenzylidene)isonicotinohydrazide methanol solvate (Liu & Shi, 2007) have also been reported. The title compound differs from (III) and (IV) as there is no solvate.

In the title compound the pyridine ring A (C1–C3/N1/C4/C5) and the benzene ring of vanilline B (C8—C13) are planar with a maximum r. m. s. deviations of 0.0061 and 0.0122 Å respectively, from their mean square planes. The dihedral angle between A/B is 15.17 (11)°. The intramolecular H-bonding of O—H···O type completes S(5) ring motif (Bernstein et al., 1995). There also exist R₂¹(7) ring motif due to intermolecular H-bondings of C—H···O and N—H···O type (Table 1, Fig. 2). The molecules are stabilized in the form of two dimensional polymeric sheets owing to intermolecular H-bondings of O—H···N type (Fig. 2).

Experimental

To a hot stirred solution of isoniazid (1.37 g, 0.01 mol) in ethanol (15 ml) was added vanillin (1.52 g, 0.01 mol). The resultant mixture was then heated under reflux. After an hour precipitates were formed. The reaction mixture was further heated about 30 min for the completion of the reaction which was monitored through TLC. The reaction mixture was cooled to room temperature, filtered and washed with hot ethanol. Yellow needles of (I) were obtained by recrystallization of the crude product in 1,4-dioxan:ethanol (1:1) after two days.