N′-(4-Hydroxy­benzyl­idene)aceto­hydrazide monohydrate

Lu-Ping Lv; Tie-Ming Yu; Wen-Bo Yu; Wei-Wei Li; Xian-Chao Hu

doi:10.1107/S160053680902892X

. 2009 Jul 29;65(Pt 8):o2007. doi: 10.1107/S160053680902892X

N′-(4-Hydroxybenzylidene)acetohydrazide monohydrate

Lu-Ping Lv ^a, Tie-Ming Yu ^a, Wen-Bo Yu ^a, Wei-Wei Li ^a, Xian-Chao Hu ^b,^*

PMCID: PMC2977428 PMID: 21583678

Abstract

In the title compound, C₉H₁₀N₂O₂·H₂O, the molecular skeleton of the acetohydrazide molecule is nearly planar [within 0.014 (1) Å]. The molecule adopts a trans configuration with respect to the C=N bond, while the side chain is slightly twisted away from the attached ring, forming a dihedral angle of 9.975 (8)°. The crystal packing exhibits a three-dimensional network composed from alternating acetohydrazide molecules and uncoordinated water molecules, which interact via N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds. A C—H⋯π interaction is also present.

Related literature

For general background to the analytical applications of Schiff bases, see: Ciemerman et al. (1997 ▶). For their mild bacteriostatic activity and potential use as oral iron-chelating drugs for the treatment of genetic disorders such as thalassemia, see: Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For a related structure, see: Li & Jian (2008 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C₉H₁₀N₂O₂·H₂O
M _r = 196.21
Monoclinic,
a = 8.352 (2) Å
b = 10.146 (3) Å
c = 12.328 (3) Å
β = 105.353 (3)°
V = 1007.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.969, T _max = 0.976
4820 measured reflections
1764 independent reflections
1569 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.100
S = 1.06
1764 reflections
147 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 I, global. DOI: 10.1107/S160053680902892X/bg2278sup1.cif

e-65-o2007-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902892X/bg2278Isup2.hkl

e-65-o2007-Isup2.hkl^{(85.1KB, 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
O1—H1⋯O2ⁱ	0.82	2.00	2.7477 (15)	152
N2—H2A⋯O1Wⁱⁱ	0.86	1.96	2.8060 (17)	166
O1W—H1F⋯O2	0.88 (2)	1.92 (2)	2.7600 (17)	159 (2)
O1W—H1E⋯O1ⁱⁱⁱ	0.85 (2)	2.01 (2)	2.8241 (17)	161 (2)
O1—H1⋯N1ⁱ	0.82	2.54	3.1864 (16)	137
C9—H9B⋯Cg1^iv	0.96	2.74	3.519 (2)	138

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C1–C6 ring.

Acknowledgments

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) for financial support.

supplementary crystallographic information

Comment

Schiff bases have attracted much attention due to their possibility of analytical application (Ciemerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952, Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound (Fig. 1).

In the title compound,C₉H₁₀N₂O₂ .H₂O, (I) the molecular skeleton is nearly planar. The molecule adopts a trans configuration with respect to the C═N bond, while the side chain is slightly twisted away from the attached ring. The dihedral angle between these two essentially planar units is 9.975 (8)°. Bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li et al., 2008).

The crystal packing exhibits a three-dimensional network composed from alternating molecules of (I) and crystalline water, which interact via N-H···O, O-H···O and O-H···N hydrogen bonds. In addition, a intermolecular C—H···π interactions is observed (Table 1 and Fig 2).

Experimental

4-Hydroxybenzaldehyde (1.22 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 95% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 435–437 K).