N′-(2,6-Dichloro­benzyl­idene)-2-hy­droxy­benzohydrazide

Yawar Baig; Hamid Latif Siddiqui; Waseeq Ahmad Siddiqui; Ghulam Mustafa; Harald Krautscheid

doi:10.1107/S1600536810035385

. 2010 Sep 25;66(Pt 10):o2603. doi: 10.1107/S1600536810035385

N′-(2,6-Dichlorobenzylidene)-2-hydroxybenzohydrazide

Yawar Baig ^a, Hamid Latif Siddiqui ^a,^*, Waseeq Ahmad Siddiqui ^b, Ghulam Mustafa ^c, Harald Krautscheid ^c

PMCID: PMC2983241 PMID: 21587580

Abstract

In the title compound, C₁₄H₁₀Cl₂N₂O₂, the dihedral angle between the two aromatic rings is 17.39 (4)°. An intramolecular O—H⋯O hydrogen bond forms a six-membered R(6)₁ ¹ring motif. In the crystal structure, intermolecular N—H⋯O and O—H⋯O hydrogen-bonding interactions occur.

Related literature

For the biological activity of Schiff bases, see: El-Masry et al. (2000 ▶); Samadhiya & Halve (2001 ▶). For the synthesis of Schiff bases, see: Siddiqui et al. (2006 ▶); Iqbal et al. (2007 ▶). For applications of Schiff bases, see: Mookherjee et al. (1989 ▶); Kumar et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₀Cl₂N₂O₂
M _r = 309.14
Monoclinic,
a = 7.5029 (6) Å
b = 23.8363 (13) Å
c = 8.0286 (7) Å
β = 109.860 (6)°
V = 1350.45 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 180 K
0.34 × 0.26 × 0.18 mm

Data collection

Stoe IPDS-2T diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.856, T _max = 0.921
21101 measured reflections
2958 independent reflections
2455 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.074
S = 1.03
2958 reflections
191 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 1999 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035385/im2223sup1.cif

e-66-o2603-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035385/im2223Isup2.hkl

e-66-o2603-Isup2.hkl^{(142.2KB, 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
N1—H1⋯N2ⁱ	0.85 (2)	2.38 (2)	3.165 (2)	153 (2)
N1—H1⋯O1ⁱ	0.85 (2)	2.45 (2)	3.158 (2)	140 (1)
O2—H2A⋯O1	0.90 (2)	1.78 (2)	2.608 (2)	153 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

HLS is grateful to the Institute of Chemistry, University of the Punjab, for financial support.

supplementary crystallographic information

Comment

Schiff base reaction products of alkyl anthranilates and their derivatives have been employed in augmenting the aroma or taste of consumable materials including perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums and beverages (Mookherjee et al., 1989). Related compounds have also shown to exhibit biological activities such as antibacterial, antimicrobial (El-Masry et al., 2000), and were investigated as herbicides (Samadhiya et al., 2001). Further, Schiff bases have also been employed as ligands for complexation of metal ions (Kumar et al., 2009). With this perspective of widespread applications of Schiff bases we embarked on the synthesis, characterization and biological evaluation of this class of compounds (Siddiqui et al., 2006; Iqbal et al., 2007). Herein, we report the synthesis and crystal structure of the title compound.

The title compound is presented in Fig.1. The two aromatic ring systems in the hydrazide are inclined at an angle of 17.39 (0.04) ° with respect to each other. The structure possesses classical inter and intra molecular hydrogen bonding. The intramolecular O–H···O type hydrogen bonding forms six membered ring motif R(6)₁¹ (Bernstein et al., 1995) which inclines at an angle of 9.73 (0.14) ° with respect to aromatic C1–C6. The intermolecular C–H···O and N—H···N type of hydrogen bonding forms nine membered ring motif R(9)₂² (Bernstein et al., 1995) where N–H···O type of hydrogen bonding interveins to form a six and a five membered ring system R(6)₂¹ and R(5)₁²(Bernstein et al., 1995), respectively (Fig. 2, table 1).

Experimental

A mixture of 2-hydroxy-benzoic acid hydrazide (1.5 g, 10.0 mmol) and 2,6-dichlorobenzaldehyde (1.7 g, 10.0 mmol) in absolute ethanol (20 ml) was heated to reflux (2 hrs.), cooled to room temperature and filtered. The off-white precipitates were washed with the same solvent and dried at room temperature to yield 2.8 g of off-white, needle-like crystals of the title compound (9.1 mmol, 90.6%). Suitable crystals were grown from a solution of CH₃OH by slow evaporation at room temperature.