N′-(5-Bromo-2-hydroxy­benzyl­idene)-3-hydroxy­benzohydrazide

Yi Nie

doi:10.1107/S1600536808002250

. 2008 Jan 25;64(Pt 2):o514. doi: 10.1107/S1600536808002250

N′-(5-Bromo-2-hydroxybenzylidene)-3-hydroxybenzohydrazide

Yi Nie ^a,^*

PMCID: PMC2960470 PMID: 21201533

Abstract

The asymmetric unit of the title compound, C₁₄H₁₁BrN₂O₃, contains two crystallographically independent molecules with slightly different conformations with respect to the aromatic rings; the dihedral angles between the two benzene rings in the two molecules are 55.0 (7) and 16.3 (7)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming chains running along the a axis.

Related literature

For related literature, see: Akitsu & Einaga (2006 ▶); Bahner et al. (1968 ▶); Butcher et al. (2005 ▶); Hodnett & Mooney (1970 ▶); Merchant & Chothia (1970 ▶); Pradeep (2005 ▶); Sigman & Jacobsen (1998 ▶).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₃
M _r = 335.16
Triclinic,
a = 6.295 (3) Å
b = 14.988 (4) Å
c = 15.423 (3) Å
α = 70.97 (2)°
β = 80.64 (2)°
γ = 78.02 (2)°
V = 1338.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 298 (2) K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.549, T _max = 0.577
11037 measured reflections
5652 independent reflections
2286 reflections with I > 2σ(I)
R _int = 0.078

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.193
S = 0.93
5652 reflections
371 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536808002250/rz2193sup1.cif

e-64-0o514-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002250/rz2193Isup2.hkl

e-64-0o514-Isup2.hkl^{(276.7KB, 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
N4—H4B⋯O6ⁱ	0.90 (5)	2.60 (8)	3.045 (9)	111 (6)
N2—H2⋯O3ⁱⁱ	0.90 (6)	2.39 (7)	3.021 (9)	127 (7)
O6—H6⋯O5ⁱⁱⁱ	0.82	2.14	2.760 (8)	132
O4—H4⋯N3	0.82	1.95	2.665 (8)	145
O3—H3⋯O2^iv	0.82	1.93	2.737 (8)	167
O1—H1⋯N1	0.82	1.94	2.654 (8)	145

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

supplementary crystallographic information

Comment

Schiff base compounds have been widely investigated due to their easy synthesis, versatile structures and widely applications (Sigman & Jacobsen, 1998; Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005). The excellent antibacterial and antitumor properties of such compounds have attracted much interest in recent years (Hodnett & Mooney, 1970; Bahner et al., 1968; Merchant & Chothia, 1970). In order to further investigate the structures of such compounds, a new Schiff base compound is reported in this paper.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1) with slightly different conformation with respect to the aromatic ring planes. The dihedral angles between the two benzene rings in the molecules are 55.0 (7) and 16.3 (7)°, respectively. The molecular conformation is stabilized by intramolecular N—H···O hydrogen bonding interactions (Table 1). In the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), forming chains running along the a axis (Fig. 2).

Experimental

The title compound was obtained by stirring of 5-bromosalicylaldehyde (0.1 mmol, 20.1 mg) and 3-hydroxybenzoic acid hydrazide (0.1 mmol, 15.2 mg) in a methanol solution (10 ml) at room temperature. Yellow block-shaped single crystals suitable for X-ray diffraction were formed from the solution after three days.