Methyl (E)-3,5-dimeth­oxy-2-{[2-(4-meth­oxy­benzo­yl)hydrazin-1-yl­idene]meth­yl}benzoate

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

doi:10.1107/S1600536812034782

. 2012 Aug 11;68(Pt 9):o2671. doi: 10.1107/S1600536812034782

Methyl (E)-3,5-dimethoxy-2-{[2-(4-methoxybenzoyl)hydrazin-1-ylidene]methyl}benzoate

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

PMCID: PMC3435694 PMID: 22969565

Abstract

In the title compound, C₁₉H₂₀N₂O₆, the azomethine [C=N = 1.269 (2) Å] double bond adopts an E conformation and the dihedral angle between the planes of the benzene rings is 17.41 (11)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(16) loops. The dimers are connected by C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (100).

Related literature

For the biological activity of benzohydraazides, see: Khan et al. (2011 ▶); Chahan et al. (2006 ▶). For a related structure, see: Zhang (2009 ▶).

Experimental

Crystal data

C₁₉H₂₀N₂O₆
M _r = 372.37
Triclinic,
a = 8.8468 (7) Å
b = 10.7392 (8) Å
c = 10.9764 (8) Å
α = 113.377 (2)°
β = 90.656 (2)°
γ = 104.695 (2)°
V = 918.52 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.28 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.972, T _max = 0.989
10426 measured reflections
3415 independent reflections
2224 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.114
S = 1.02
3415 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 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/S1600536812034782/hb6920sup1.cif

e-68-o2671-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034782/hb6920Isup2.hkl

e-68-o2671-Isup2.hkl^{(167.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034782/hb6920Isup3.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
N1—H1A⋯O5ⁱ	0.84 (2)	2.13 (2)	2.969 (2)	172.3 (19)
C18—H18B⋯N2ⁱⁱ	0.96	2.62	3.501 (3)	153
C19—H19B⋯O5ⁱⁱⁱ	0.96	2.57	3.511 (3)	168

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

supplementary crystallographic information

Comment

Phenyl hydrazones represent a very important class of bioactive organic compounds and are reported to have antibacterial, anticancer, antifungal, herbicidal activities, anticonvulsant, antiproliferative, antioxidant and antidiabetic activities (e.g. Khan et al., 2011; Chahan et al., 2006). The title compound was prepared as a part of our ongoing research to synthesize libraries of different bioactive benzohydrazone. The structure of title compound (Fig. 1) is similar to that of the previously published 4-Methoxy-N'-(2-methoxybenzylidene)-benzohydrazide (Zhang, 2009) with the difference that 2-methoxy benzne ring is replaced by 3,5-dimethoxybenzoate moiety (C9–C14). The azomethine (C=N,1.269 (2) Å) double bond adopt an E conformation (Fig. 1). The benzene rings (C1–C6 and C9–C14) subtend a dihedral angle 17.41 (11)° between them and maximum deviation of 0.014 (2) Å for C6 atom from the root mean square plane of 4-methoxybenzene ring (C1–C6).

The crystal structure features N1—H1A···O5, C18—H18B···N2 and C19—H19B···O5 intrmolecular hydrogen bonds and inked to form chains (symmetry codes as in Table 2) arranged parallel to (100) in (Fig. 2).

Experimental

A mixture of 2 mmol of each 4-methoxybenzohydrazide and methyl 2-formyl-3,5-dimethoxybenzoate and catalytical amount of acetic acid was refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion of reaction, the solvent was evaporated by vacuum to afford the crude product (0.610 g, yield 82%), which was re-crystallized from methanol solution to yield colourless blocks of the title compound.