(E)-4-Meth­oxy-N′-[(pyridin-4-yl)methyl­idene]benzohydrazide monohydrate

Muhammad Taha; Humera Naz; Aqilah Abd Rahman; Nor Hadiani Ismail; Yousuf Sammer

doi:10.1107/S1600536812034988

. 2012 Aug 25;68(Pt 9):o2778. doi: 10.1107/S1600536812034988

(E)-4-Methoxy-N′-[(pyridin-4-yl)methylidene]benzohydrazide monohydrate

Muhammad Taha ^a, Humera Naz ^a,^b, Aqilah Abd Rahman ^a,^b, Nor Hadiani Ismail ^a, Yousuf Sammer ^c,^*

PMCID: PMC3435810 PMID: 22969656

Abstract

In the title compound, C₁₄H₁₃N₃O₂·H₂O, the azomethine double bond adopts an E conformation and the N—N=C—C torsion angle is 178.37 (19)°. The dihedral angle between the benzene and pyridine rings is 5.58 (12)° and the C atom of the methoxy group is roughly coplanar with its attached ring [deviation = 0.157 (3) Å]. In the crystal, the components are linked by O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds, forming (001) sheets. The water O atom accepts one N—H⋯O and two C—H⋯O interactions from the adjacent organic molecule.

Related literature

For the biological activity of benzohydraazides, see: Bayrak et al. (2009 ▶). For the crystal structures of related benzohydrazides, see: Taha et al. (2012) ▶; Fun et al. (2011 ▶); Lu et al. (2009 ▶); Zhang (2009a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₃N₃O₂·H₂O
M _r = 273.29
Monoclinic,
a = 6.6878 (5) Å
b = 7.0420 (5) Å
c = 29.249 (2) Å
β = 94.233 (2)°
V = 1373.74 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.20 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.981, T _max = 0.991
7767 measured reflections
2560 independent reflections
1548 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.146
S = 1.03
2560 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034988/hb6930sup1.cif

e-68-o2778-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034988/hb6930Isup2.hkl

e-68-o2778-Isup2.hkl^{(125.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034988/hb6930Isup3.cml

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
O1W—H1⋯O1ⁱ	0.84	2.00	2.811 (2)	162
O1W—H2⋯N3ⁱⁱ	0.91	2.11	2.956 (3)	154
N1—H1A⋯O1W	0.86	2.08	2.911 (2)	161
C1—H1B⋯O1W	0.93	2.54	3.440 (3)	162
C8—H8A⋯O1W	0.93	2.48	3.272 (3)	143
C11—H11A⋯O2ⁱⁱⁱ	0.93	2.47	3.375 (3)	165

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

supplementary crystallographic information

Comment

The diverse structural features and wide range of biological activities make Benzohydrazides as an importent class of organic compounds. The title compound is an structure analogue of Benzohydrazide, synthesize as a part of our ongoing research to study their varoius biological activities. The structure of title compound (Fig. 1) is similar to that of our recently published benzohydrazide derivative (E)-N'-(3,4-Dimethoxybenzylidene)-4-methoxybenzohydrazide (Taha et al., 2012, Pv2573) with the difference that 3,4-dimethoxy phenyl ring is replaced by pyridine ring (N3/C9–C13). The azomethine (C=N,1.269 (3) Å) double bond adopt an E conformation (Fig. 1) with the torsion angle of 178.3 (19)° (N1–N2–C8–C9). Phenyl and pyridine rings (C1–C6 and N3/C9–C13) have a dihedral angle of 5.58 (12)° between them and maximum deviation of 0.006 (3) Å for C13 atoms from the root mean square plane. The bond lengths and angle were found to be similar as in structurally realted compounds (Fun et al., 2011, Lu et al., 2009, Zhang et al., 2009). In the crystal structure molecules are consolidated by C11—H11A···O2 intermolecular hydrogen bonds (Fig.2) and extended to form a two-dimensional-network due to O1W—H1···O1 and O1W—H2···N3 (symmetry codes as in Table 2) intermolecular linkages made by water solvates (Fig. 2).

Experimental

A mixture of 2 mmol of 4-methoxybenzohydrazide (0.332 g), 2 mmol isonicotinaldehyde (0.214 g) and catalytical amount of acetic acid was refluxed in methanol (20 ml) for 3 h. The progress of reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated by vacuum to afford the crude product, which was dissolved and recrystallized from methanol to obtain colourless blocks (0.418 g in 82% yield).