N′-(3,4-Dimeth­oxy­benzyl­idene)benzo­hydrazide

Saeedeh Hashemian; Vahideh Ghaeinee; Behrouz Notash

doi:10.1107/S1600536810052128

. 2010 Dec 18;67(Pt 1):o171. doi: 10.1107/S1600536810052128

N′-(3,4-Dimethoxybenzylidene)benzohydrazide

Saeedeh Hashemian ^a,^*, Vahideh Ghaeinee ^a, Behrouz Notash ^b

PMCID: PMC3050232 PMID: 21522678

Abstract

The crystal structure of the title Schiff base compound, C₁₆H₁₆N₂O₃, is characterized by chains of molecules linked by intermolecular N—H⋯O hydrogen bonds running along the c axis. Further stabilization is provided by weak C—H⋯O contacts. The dihedral angle between the aromatic rings is 38.31 (7)°.

Related literature

For related structures see: Alhadi et al. (2009 ▶); Das & Pal (2004 ▶); Tamboura et al. (2009 ▶); Zhou et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M _r = 284.31
Monoclinic,
a = 12.612 (3) Å
b = 11.291 (2) Å
c = 9.892 (2) Å
β = 95.46 (3)°
V = 1402.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 K
0.5 × 0.4 × 0.15 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical shape of crystal determined optically T _min = 0.954, T _max = 0.984
9840 measured reflections
3758 independent reflections
3054 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.131
S = 1.03
3758 reflections
200 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052128/bt5434sup1.cif

e-67-0o171-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052128/bt5434Isup2.hkl

e-67-0o171-Isup2.hkl^{(184.3KB, 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
C9—H9⋯O3ⁱ	0.957 (19)	2.455 (19)	3.2702 (18)	142.9 (15)
C7—H7B⋯O3ⁱⁱ	0.96	2.40	3.2434 (18)	146
N2—H2A⋯O3ⁱ	0.87 (2)	2.07 (2)	2.9219 (16)	163.2 (18)

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

Acknowledgments

We are grateful to the Islamic Azad University, Yazd Branch, for financial support.

supplementary crystallographic information

Comment

Schiff bases are important organic compounds. Metal complexes based on Schiff bases have received considerable attention because they can be utilized as a model of active centers in various complexes (Tamboura et al., 2009; Das & Pal, 2004).

We report here the crystal structure of N'-(3,4-dimethoxybenzylidene)-benzohydrazide. The title compound was synthesized from the reaction of 3,4-dimethoxy benzaldehyde and benzoylhydrazine in methanol. The asymmetric unit of the title compound is shown in Fig. 1. The bond lengths and angles are comparable to those observed for N'-(2,4-dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide (Alhadi et al., 2009) and N'-(3,4-dimethoxybenzylidene)acetohydrazide (Zhou et al., 2009). The crystal structure is characterized by chains of running along the c-axis. The molecules in a chain are linked by intermolecular N—H···O hydrogen bonds. Further stabilization is provided by weak C—H···O contacts.

Experimental

To a methanol solution (20 ml) of benzoylhydrazine (1.0 mmol, 0.135 g), 3,4-dimethoxybenzaldehyde (1.0 mmol, 0.165 g), a few drops of acetic acid were added. The mixture was refluxed for 6 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and finally dried in air (m.p: 181–183 °C, yield: 81%). Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature.