(E)-N′-(2-Chloro­benzyl­idene)-3,5-di­hydroxy­benzohydrazide dihydrate

Ling Yuan; Yi Nan; Jing-Yuan Li; Xiu-Lan Huang

doi:10.1107/S1600536811042681

. 2011 Oct 22;67(Pt 11):o3017. doi: 10.1107/S1600536811042681

(E)-N′-(2-Chlorobenzylidene)-3,5-dihydroxybenzohydrazide dihydrate

Ling Yuan ^a,^c, Yi Nan ^b, Jing-Yuan Li ^c, Xiu-Lan Huang ^c,^*

PMCID: PMC3247416 PMID: 22220034

Abstract

In the Schiff base molecule of the title compound, C₁₄H₁₁ClN₂O₃·2H₂O, the benzene rings form a dihedral angle of 20.6 (1)°. The water molecules of crystallization are involved in the formation of a three-dimensional hydrogen-bonding network via O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Brückner et al. (2000 ▶); Harrop et al.(2003 ▶); Zhang et al. (2008 ▶). For related structures, see: Diao et al. (2007 ▶); Jiang et al. (2008 ▶); Huang et al. (2008 ▶); Deng et al. (2009 ▶).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₃·2H₂O
M _r = 326.73
Monoclinic,
a = 8.023 (2) Å
b = 11.852 (4) Å
c = 16.318 (5) Å
β = 100.387 (4)°
V = 1526.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.44 × 0.12 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
12729 measured reflections
3522 independent reflections
2286 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.140
S = 1.03
3522 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042681/cv5172sup1.cif

e-67-o3017-sup1.cif^{(18KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042681/cv5172Isup2.hkl

e-67-o3017-Isup2.hkl^{(172.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042681/cv5172Isup3.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
O2—H2B⋯O5	0.82	1.87	2.674 (3)	168
O3—H3A⋯O1ⁱ	0.82	1.85	2.665 (2)	169
N2—H2A⋯O2ⁱⁱ	0.86	2.36	3.196 (3)	164
O4—H4B⋯O1	0.85	2.12	2.960 (4)	171
O5—H5A⋯O4ⁱⁱⁱ	0.85	1.99	2.816 (4)	163
O5—H5B⋯O3^iv	0.85	2.14	2.902 (3)	150

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

Acknowledgments

This project was supported by the National Natural Science Foundation of China (grant No. 81102893) and 2011 Ningxia Science and Technology Key Projects (grant No. 2011-25) and 2009 Ningxia Science and Technology Key Projects (grant No. 232).

supplementary crystallographic information

Comment

Schiff base compounds are known to exhibit antibacterial and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Zhang et al., 2008). In order to expand this filed, we report here the structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with those found in the related compounds (Diao et al., 2007; Deng et al., 2009; Huang et al., 2008, Jiang et al., 2008). In the Shiff base molecule, two benzene rings form a dihedral angle of 20.6 (1)°.

In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) consolidate the crystal packing.

Experimental

2-Chlorobenzaldehyde (0.1 mmol, 14.1 mg) and 3,5-dihydroxybenzhydrazide (0.1 mmol, 16.8 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature for 1 h and filtered. After keeping the filtrate in air for three days, yellow crystals were formed.