3-Bromo-N′-(2-hydr­oxy-3,5-diiodo­benzyl­idene)benzohydrazide monohydrate

Jing-Heng Ning; Xiao-Wu Xu

doi:10.1107/S1600536809010964

. 2009 Mar 28;65(Pt 4):o905–o906. doi: 10.1107/S1600536809010964

3-Bromo-N′-(2-hydroxy-3,5-diiodobenzylidene)benzohydrazide monohydrate

Jing-Heng Ning ^a,^*, Xiao-Wu Xu ^b

PMCID: PMC2968873 PMID: 21582609

Abstract

Crystals of the title compound, C₁₄H₉BrI₂N₂O₂·H₂O, were obtained from a condensation reaction of 3-bromobenzohydrazide with 3,5-diiodosalicylaldehyde. The Schiff base molecule assumes an E configuration with respect to the C=N bond, and the dihedral angle between the two benzene rings is 6.9 (2)°. An intramolecular O—H⋯N hydrogen bond is observed in the Schiff base molecule and may contribute to its overall near planarity. In the crystal structure, molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds, forming layers parallel to the bc plane. Short intermolecular I⋯O contacts [2.930 (5) Å] are also found, linking the molecules into zigzag chains along b.

Related literature

For the biological activity of Schiff bases, see: Bedia et al. (2006 ▶); Richardson & Bernhardt (1999 ▶); Koh et al. (1998 ▶); Prasad et al. (2007 ▶). For metal complexes of Schiff bases, see: Adams et al. (2000 ▶); Ainscough et al. (1998 ▶); Roth et al. (2007 ▶). For related structures, see: Fun et al. (2008 ▶); Butcher et al. (2007 ▶); Zhi & Yang (2007 ▶); Ejsmont et al. (2008 ▶); Yathirajan et al. (2007 ▶); Narayana et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For short intermolecular I⋯O contacts, see, for example: Britton (2003 ▶).

Experimental

Crystal data

C₁₄H₉BrI₂N₂O₂·H₂O
M _r = 588.96
Monoclinic,
a = 15.181 (3) Å
b = 7.611 (2) Å
c = 15.516 (3) Å
β = 110.628 (3)°
V = 1677.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 6.14 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.261, T _max = 0.293
13552 measured reflections
3656 independent reflections
2651 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.090
S = 1.00
3656 reflections
209 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010964/sj2600sup1.cif

e-65-0o905-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010964/sj2600Isup2.hkl

e-65-0o905-Isup2.hkl^{(179.3KB, 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
O3—H3A⋯O1ⁱ	0.86 (4)	2.50 (6)	3.131 (6)	132 (6)
N2—H2⋯O3ⁱⁱ	0.89 (4)	2.08 (6)	2.934 (6)	162 (7)
O1—H1⋯N1	0.82	1.87	2.579 (6)	144

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

Acknowledgments

We are grateful for financial support of this work from the Natural Science Foundation of Hunan Province, People’s Republic of China (Project No. 07 J J6023).

supplementary crystallographic information

Comment

Schiff bases have been demonstrated to possess interesting biological activities (Bedia et al., 2006; Richardson & Bernhardt, 1999; Koh et al., 1998; Prasad et al., 2007). These compounds have been widely used as versatile ligands in coordination chemistry (Adams et al., 2000; Ainscough et al., 1998; Roth et al., 2007). Recently, the crystal structures of such compounds have been extensively reported (Fun et al., 2008; Butcher et al., 2007; Zhi & Yang, 2007). In this paper, the new title Schiff base, (I), Fig. 1, is reported.

The asymmetric unit of (I) contains a Schiff base molecule and a water molecule of crystallization. The Schiff base molecule assumes an E configuration with respect to the C═N bond. The dihedral angle between the two benzene rings is 6.9 (2)°, indicating that the molecule is essentially planar. An intramolecular O—H···N hydrogen bond is observed in the Schiff base molecule and may contribute to its overall planarity. All bond lengths in (I) are within normal ranges (Allen et al., 1987) and comparable to the corresponding values in other similar compounds (Ejsmont et al., 2008; Yathirajan et al., 2007; Narayana et al., 2007).

In the crystal structure, molecules are linked through intermolecular O–H···O and N–H···O (Table 1) hydrogen bonds, forming layers parallel to the bc plane (Fig. 2). Additional short intermolecular I1···O12ⁱ contacts, 2.930 (5)Å, ⁱ = 1-x, -1/2+y, 1/2+z, are also observed linking molecules into zig-zag chains along b. Similar short I···O contacts have been reported previously (Britton, 2003).

Experimental

3-Bromobenzohydrazide (1.0 mmol, 215.2 mg) and 3,5-diiodosalicylaldehyde (1.0 mmol, 374.9 mg) were stirred at room temperature for two hours. The filtrate was kept in air for a week to obtain yellow block-shaped crystals of (I).