(E)-N′-(3,5-Dibromo-2-hydroxy­benzyl­idene)-2-nitro­benzohydrazide methanol solvate

Heng-Yu Qian; Da-Ping Qu

doi:10.1107/S160053680903311X

. 2009 Aug 26;65(Pt 9):o2237. doi: 10.1107/S160053680903311X

(E)-N′-(3,5-Dibromo-2-hydroxybenzylidene)-2-nitrobenzohydrazide methanol solvate

Heng-Yu Qian ^a,^*, Da-Ping Qu ^b

PMCID: PMC2969957 PMID: 21577635

Abstract

In the title compound, C₁₄H₉Br₂N₃O₄·CH₃OH, the Schiff base molecule adopts an E geometry with respect to the C=N bond and the benzene rings are oriented at a dihedral angle of 45.3 (2)°. An intramolecular O—H⋯N hydrogen bond helps to establish the conformation. In the crystal, the methanol solvent molecule is linked to the Schiff base molecule through an O—H⋯O hydrogen bond and intermolecular N—H⋯O hydrogen bonds link the components to form layers parallel to the bc direction.

Related literature

For our previous work in this area, see: Yin, Qian et al. (2007 ▶); Yin, Guo et al. (2007 ▶); Qian et al. (2009 ▶).

Experimental

Crystal data

C₁₄H₉Br₂N₃O₄·CH₄O
M _r = 475.10
Monoclinic,
a = 18.981 (1) Å
b = 10.054 (2) Å
c = 19.746 (2) Å
β = 110.974 (2)°
V = 3518.6 (8) Å³
Z = 8
Mo Kα radiation
μ = 4.64 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.490, T _max = 0.524
10461 measured reflections
3784 independent reflections
2670 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.094
S = 1.02
3784 reflections
232 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.66 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/S160053680903311X/hb5053sup1.cif

e-65-o2237-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903311X/hb5053Isup2.hkl

e-65-o2237-Isup2.hkl^{(185.6KB, 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⋯N1	0.82	1.87	2.587 (3)	146
O5—H5⋯O2	0.82	1.94	2.735 (4)	165
N2—H2⋯O5ⁱ	0.893 (10)	1.958 (13)	2.840 (3)	169 (4)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As part of our ongoing studies of Schiff bases (Yin, Qian et al., 2007; Yin, Guo et al., 2007; Qian et al., 2009), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The Schiff base molecule adopts an E geometry with respect to the C=N bond, and there forms an intramolecular O—H···N hydrogen bond. The two benzene rings forms a dihedral angle of 45.3 (2)°. The dihedral angle between the O3/N3/O4 plane and the C9—C14 benzene ring is 37.1 (2)°. The methanol molecule is linked to the Schiff base molecule through the O—H···O hydrogen bond (Table 1). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form layers parallel to the bc direction (Fig. 2).

Experimental

2-Nitrobenzohydrazide (1 mmol, 0.181 g) and 3,5-dibromosalicylaldehyde (1 mmol, 0.280 g) were dissolved in anhydrous methanol (15 ml). The mixture was stirred for several minutes at room temperature. The product was isolated and recrystallized from methanol, colourless blocks of (I) were obtained after five days.