N′-(4-Hydr­oxy-3-methoxy­benzyl­idene)-4-methoxy­benzohydrazide monohydrate

Jiu-Fu Lu; Suo-Tian Min; Hong-Guang Ge; Xiao-Hui Ji

doi:10.1107/S1600536809034242

. 2009 Aug 29;65(Pt 9):o2301. doi: 10.1107/S1600536809034242

N′-(4-Hydroxy-3-methoxybenzylidene)-4-methoxybenzohydrazide monohydrate

Jiu-Fu Lu ^a,^*, Suo-Tian Min ^a, Hong-Guang Ge ^a, Xiao-Hui Ji ^a

PMCID: PMC2970025 PMID: 21577690

Abstract

In the title compound, C₁₆H₁₆N₂O₄·H₂O, the dihedral angle between the two aromatic rings is 19.6 (2)°. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For our previous work in this area, see: Lu et al. (2008a ▶,b ▶,c ▶). For related structures, see: Abdul Alhadi et al. (2009 ▶); Mohd Lair et al. (2009 ▶); Narayana et al. (2007 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₄·H₂O
M _r = 318.32
Monoclinic,
a = 7.942 (1) Å
b = 21.273 (2) Å
c = 10.246 (1) Å
β = 106.596 (2)°
V = 1659.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.970, T _max = 0.972
9533 measured reflections
3338 independent reflections
2291 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.127
S = 1.04
3338 reflections
220 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034242/hb5071sup1.cif

e-65-o2301-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034242/hb5071Isup2.hkl

e-65-o2301-Isup2.hkl^{(163.8KB, 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
O5—H5A⋯N1ⁱ	0.846 (9)	2.487 (15)	3.1257 (18)	133.0 (17)
O5—H5A⋯O3ⁱ	0.846 (9)	2.107 (13)	2.8927 (18)	154 (2)
O5—H5B⋯O3ⁱⁱ	0.856 (9)	1.884 (10)	2.7401 (17)	179 (2)
N2—H2B⋯O2ⁱ	0.895 (9)	2.185 (12)	3.0398 (18)	159.6 (19)
O2—H2⋯O5ⁱⁱⁱ	0.82	1.77	2.5775 (17)	170

Open in a new tab

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

Acknowledgments

The authors acknowledge the Scientific Research Foundation of Shaanxi University of Technology (Project No. SLGQD0708).

supplementary crystallographic information

Comment

Schiff bases and their metal complexes have received much attention in recent years. As part of our investigation on the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report herein the crystal structure of the title new Schiff base compound, (I).

The title compound (Fig. 1), consists of a Schiff base molecule and a water molecule of crystallization. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Narayana et al., 2007). The dihedral angle between the two aromatic rings is 19.6 (2)°, indicating that they the molecule is twisted.

In the crystal structure, the molecules are linked into a three-dimensional network by intermolecular N—H···O, O—H···N and O—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

The title compound was prepared by the Schiff base condensation of 4-hydroxy-3-methoxybenzaldehyde (0.1 mol) and 4-methoxybenzohydrazide (0.1 mmol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Colourless blokcs of (I) were obatined by slow evaporation of a 95% ethanol solution at room temperature.