N′-(3,5-Di-tert-butyl-4-hydroxy­benzyl­idene)-2-hydroxy­benzohydrazide methanol solvate

Wagee A Yehye; Azhar Ariffin; Seik Weng Ng

doi:10.1107/S1600536808020746

. 2008 Jul 9;64(Pt 8):o1452. doi: 10.1107/S1600536808020746

N′-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-hydroxybenzohydrazide methanol solvate

Wagee A Yehye ^a, Azhar Ariffin ^a,^*, Seik Weng Ng ^a

PMCID: PMC2962083 PMID: 21203167

Abstract

The asymmetric unit of the title compound, C₂₂H₂₈N₂O₃·CH₄O, consists of two independent Schiff base molecules and two independent methanol solvent molecules. In one Schiff base molecule, the 2-hydroxy group forms an intramolecular hydrogen bond with the amide O atom, whereas in the other Schiff base molecule, the 2-hydroxy-substituted benzene ring is oriented so that the 2-hydroxy group serves as hydrogen-bond acceptor for the amide NH group. In the crystal structure, Schiff base molecules interact with methanol solvent to furnish a hydrogen-bonded chain.

Related literature

For references to other crystal structures of substituted benzylidene-2-hydroxybenzohydrazides, see: Yehye et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₂₈N₂O₃·CH₄O
M _r = 400.51
Monoclinic,
a = 24.184 (4) Å
b = 11.198 (2) Å
c = 33.112 (5) Å
β = 96.389 (3)°
V = 8911 (2) Å³
Z = 16
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.35 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
22590 measured reflections
7825 independent reflections
4711 reflections with I > 2σ(I)
R _int = 0.090

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.239
S = 1.09
7825 reflections
529 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020746/lh2656sup1.cif

e-64-o1452-sup1.cif^{(33.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020746/lh2656Isup2.hkl

e-64-o1452-Isup2.hkl^{(382.9KB, 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—H1o⋯O2	0.84	1.78	2.528 (4)	147
O4—H4o⋯O8	0.84	1.75	2.578 (4)	167
N1—H1n⋯O5ⁱ	0.88	2.10	2.763 (4)	132
N3—H3n⋯O4	0.88	1.88	2.592 (4)	137
O7—H7o⋯N2	0.84	2.16	2.900 (4)	148
O8—H8o⋯O7	0.84	2.00	2.704 (5)	140

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge th SAGA grant (No. 06-02-03-0147) for supporting this study, and the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The crystal structures of a number of substituted benzylidene-2-hydroxybenzohydrazides have been reported, along with that of the 2,4-dimethoxy derivative, which crystallizes as an ethanol solvate (Yehye et al., 2008 and references cited within). In the title compound , the asymmetric unit consists of two Schiff-base and two solvent molecules. In one Schiff base molecule, the hydroxy group forms an intramolecular hydrogen bond with the amido C=O oxygen atom whereas in the other Schiff base molecule, the phenylene ring is rotated so that the 2-hydroxy group now serves as hydrogen-bond acceptor to the amido NH nitrogen atom (Fig. 1). The Schiff-base molecules interact with the two lattice methanol molecules to furnish a hydrogen-bonded chain.

Experimental

2-Hydroxybenzohydrazide (0.5 g, 4 mmol) and 3,5-di-tert-butyl-4-hydroxybenzaldehyde (0.9 g, 4 mmol) were heated in ethanol (30 ml) for 2 h. The solvent was removed by evaporation and the product recrystallized from methanol.