N′-[(1E)-3-Bromo-5-chloro-2-hy­droxy­benzyl­idene]-4-tert-butyl­benzo­hydrazide ethanol monosolvate

A Thirugnanasundar; K Parthipan; V S Xavier Anthonisamy; G Chakkaravarthi; G Rajagopal

doi:10.1107/S160053681104027X

. 2011 Oct 5;67(Pt 11):o2857. doi: 10.1107/S160053681104027X

N′-[(1E)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-tert-butylbenzohydrazide ethanol monosolvate

A Thirugnanasundar ^a, K Parthipan ^b, V S Xavier Anthonisamy ^c, G Chakkaravarthi ^d,^*, G Rajagopal ^c,^*

PMCID: PMC3247593 PMID: 22219898

Abstract

In the title compound, C₁₈H₁₈BrClN₂O₂·C₂H₆O, the hydroxy group forms an intramolecular O—H⋯N hydrogen bond, which influences the conformation of the Shiff base molecule, where the two aromatic rings form a dihedral angle of 21.67 (8)°. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds link two Shiff base molecules and two solvent molecules into a centrosymmetric heterotetramer. Weak intermolecular C—H⋯O interactions link further tetramers related by translation along the a axis into chains.

Related literature

For the biological activity of Schiff base derivatives, see: Dao et al. (2000 ▶); Karthikeyan et al. (2006 ▶); Prabhakaran et al. (2006 ▶); Shivakumar et al. (2008 ▶). For related structures, see: Fun et al. (2008 ▶); Thirugnanasundar et al. (2011 ▶).

Experimental

Crystal data

C₁₈H₁₈BrClN₂O₂·C₂H₆O
M _r = 455.77
Triclinic,
a = 9.2478 (4) Å
b = 9.4057 (4) Å
c = 12.7838 (5) Å
α = 78.811 (2)°
β = 79.235 (1)°
γ = 79.469 (2)°
V = 1059.17 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.09 mm⁻¹
T = 295 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.613, T _max = 0.680
27712 measured reflections
6728 independent reflections
3460 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.180
S = 1.03
6728 reflections
248 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104027X/cv5157sup1.cif

e-67-o2857-sup1.cif^{(27KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104027X/cv5157Isup2.hkl

e-67-o2857-Isup2.hkl^{(322.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104027X/cv5157Isup3.cml

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	1.86	2.577 (3)	145
N2—H2⋯O3	0.86	2.10	2.865 (3)	147
O3—H3⋯O2ⁱ	0.82	1.94	2.755 (3)	171
C14—H14⋯O2ⁱⁱ	0.93	2.54	3.418 (3)	157

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

Acknowledgments

The authors acknowledge SAIF, IIT, Madras, for the X-ray data collection.

supplementary crystallographic information

Comment

Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006). Schiff bases are also known to exhibit anticancer, antibacterial and antifungal activities (Dao et al., 2000; Karthikeyan et al., 2006). Herewith we present the title compound (I), which is a new Schiff base.

In (I) (Fig. 1), the geometric parameters are comparable with the those reported for similar structures ( Fun et al., 2008; Thirugnanasundar et al., 2011). The dihedral angle between the two aromatic rings is 21.67 (8)°. Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link two Shiff base molecules and two solvent molecules into centrosymmetric tetramer (Fig. 2). Weak intermolecular C—H···O interactions (Table 1) link further the tetramers related by translation along axis a into chains.

Experimental

4-tert-Butylbenzoichydrazide (5 mmol) was dissolved in 20 mL of dry ethanol with stirring and warming over a period of 10 min. To the warm hydrazide solution, 3-bromo-5-chloro salicylaldehyde (5 mmol) in 20 mL of dry ethanol was added and the mixture was stirred and slowly refluxed for 2 h. The mixture was then cooled down to room temperature when pale yellow crystalline compound precipitated. The compound was collected by filtration, washed with cold ethanol and dried in vacuum. Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature. Melting Point: 498 - 500 K.