N′-(5-Bromo-2-hydroxy­benzyl­idene)-3,4,5-trihydroxy­benzohydrazide dihydrate

Abeer A Alhadi; Hapipah M Ali; Subramaniam Puvaneswary; Ward T Robinson; Seik Weng Ng

doi:10.1107/S1600536808022708

. 2008 Jul 23;64(Pt 8):o1584. doi: 10.1107/S1600536808022708

N′-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide dihydrate

Abeer A Alhadi ^a, Hapipah M Ali ^a, Subramaniam Puvaneswary ^a, Ward T Robinson ^a, Seik Weng Ng ^a,^*

PMCID: PMC2962201 PMID: 21203282

Abstract

The title compound, C₁₄H₁₁BrN₂O₅·2H₂O, crystallizes as hydrogen-bonded sheets. The 2-hydroxy group on the benzylidene group forms an intramolecular hydrogen bond to the N atom of the C=N double bond. The amino N atom is a hydrogen-bond donor to a water molecule. The hydroxy group on the benzohydrazide group is a hydrogen-bond donor to one acceptor site, whereas each water molecule is a hydrogen-bond donor to two acceptor sites.

Related literature

For the structure of a similar Schiff-base ligand, 5-bromosalicylaldehyde benzoylhydrazone, see: Liu et al. (2006 ▶).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₅·2H₂O
M _r = 403.19
Monoclinic,
a = 30.8424 (8) Å
b = 3.7999 (1) Å
c = 12.8484 (4) Å
β = 90.280 (2)°
V = 1505.79 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.77 mm⁻¹
T = 100 (2) K
0.30 × 0.03 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.658, T _max = 0.921
9964 measured reflections
3424 independent reflections
2914 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.155
S = 1.22
3424 reflections
241 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.08 e Å⁻³
Δρ_min = −1.82 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022708/bt2751sup1.cif

e-64-o1584-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022708/bt2751Isup2.hkl

e-64-o1584-Isup2.hkl^{(167.9KB, 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—H1o⋯N1	0.84 (1)	1.91 (5)	2.616 (6)	141 (7)
O3—H3o⋯O2w	0.84 (1)	1.96 (4)	2.736 (6)	153 (7)
O4—H4o⋯O2wⁱ	0.84 (1)	1.81 (3)	2.623 (8)	163 (9)
O5—H5o⋯O2ⁱⁱ	0.84 (1)	1.93 (2)	2.764 (5)	171 (7)
O1w—H1w1⋯O2ⁱⁱⁱ	0.84 (1)	1.98 (2)	2.812 (5)	170 (6)
O1w—H1w2⋯O1ⁱⁱ	0.84 (1)	2.09 (2)	2.914 (6)	167 (6)
O2w—H2w1⋯O3^iv	0.84 (1)	2.13 (5)	2.845 (9)	142 (8)
O2w—H2w2⋯O4^v	0.84 (1)	2.12 (4)	2.900 (8)	154 (8)

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

Acknowledgments

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

This study extends the structural study on the Schiff base, 5-bromosalicylaldehyde benzoylhydrazone (Liu et al., 2006) as the title compound (Scheme I, Fig. 1) has several hydroxy groups on one of the aromatic rings. The compound crystallizes with two lattice water molecules. Hydrogen bonding interactions (Table 1) give rise to a layer motif.

Experimental

3,4,5-Trihydroxybenzoylhydrazide (0.65 g, 3.5 mmol) and 5-bromo-2-hydroxybenzaldehyde (0.70 g, 3.5 mmol) were heated for 12 h in ethanol. The solvent was removed and the product recrystallized from ethanol.