2′-(3-Bromo-5-chloro-2-hydroxy­benzyl­idene)isonicotinohydrazide methanol solvate

Chun-Bao Tang

doi:10.1107/S1600536808019648

. 2008 Jul 5;64(Pt 8):o1381. doi: 10.1107/S1600536808019648

2′-(3-Bromo-5-chloro-2-hydroxybenzylidene)isonicotinohydrazide methanol solvate

Chun-Bao Tang ^a,^*

PMCID: PMC2962014 PMID: 21203101

Abstract

The title Schiff base compound, C₁₃H₉BrClN₃O₂·CH₄O, was derived from the condensation reaction of 3-bromo-5-chlorosalicylaldehyde with isonicotinohydrazide. The dihedral angle between the benzene and pyridine rings is 5.9 (2)°. In the crystal structure, molecules are linked through N—H⋯O, O—H⋯O, and O—H⋯Br intermolecular hydrogen bonds, forming dimers and chains. There is also an intramolecular O—H⋯N hydrogen bond.

Related literature

For related structures, see: Tang, (2006 ▶); Tang, (2007a ▶,b ▶,c ▶,d ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₉BrClN₃O₂·CH₄O
M _r = 386.63
Triclinic,
a = 7.531 (1) Å
b = 8.735 (1) Å
c = 12.130 (2) Å
α = 80.853 (2)°
β = 77.781 (2)°
γ = 86.721 (2)°
V = 769.73 (19) Å³
Z = 2
Mo Kα radiation
μ = 2.86 mm⁻¹
T = 298 (2) K
0.32 × 0.32 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.461, T _max = 0.481 (expected range = 0.407–0.424)
4529 measured reflections
3254 independent reflections
2438 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.093
S = 1.01
3254 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.36 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019648/at2582sup1.cif

e-64-o1381-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019648/at2582Isup2.hkl

e-64-o1381-Isup2.hkl^{(159.6KB, 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
N2—H2⋯O3ⁱ	0.890 (10)	2.005 (15)	2.876 (4)	166 (4)
O3—H3⋯Br1	0.82	3.05	3.641 (3)	131
O3—H3⋯O1	0.82	2.62	3.268 (4)	137
O3—H3⋯O1ⁱⁱ	0.82	2.55	3.114 (4)	127
O1—H1⋯N1	0.82	1.87	2.590 (3)	146

Open in a new tab

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

Acknowledgments

Financial support from the Jiaying University research fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Recently, the author has reported the structures of several Schiff base compounds (Tang, 2006; Tang, 2007a,b,c,d) and, in continuation of work in this area, reports herein the crystal structure of the title new Schiff base compound, (I).

In the title compound (Fig. 1), the dihedral angle between the benzene ring and the pyridine ring is 5.9 (2)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8, and N1—N2—C8—C9 are 0.4 (2), 2.3 (2), and 1.9 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through N–H···O, O–H···O, and O–H···Br intermolecular hydrogen bonds (Table 1), forming dimers (Fig. 2).

Experimental

3-Bromo-5-chlorosalicylaldehyde (0.1 mmol, 23.5 mg) and isonicotinohydrazide (0.1 mmol, 13.7 mg) were dissolved in a methanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless block-like crystals of the compound were formed by slow evaporation of the solvent over several days.