N′-(3,5-Dichloro-2-hy­droxy­benzyl­idene)-4-(dimethyl­amino)­benzohydrazide methanol monosolvate

Huanzhi Xu; Jingya Sun

doi:10.1107/S1600536812010148

. 2012 Mar 10;68(Pt 4):o1042. doi: 10.1107/S1600536812010148

N′-(3,5-Dichloro-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate

Huanzhi Xu ^a, Jingya Sun ^a,^*

PMCID: PMC3344003 PMID: 22589912

Abstract

The title compound, C₁₆H₁₅Cl₂N₃O₂·CH₃OH, a Schiff base molecule, is prepared by the reaction of 3,5-dichlorosalicylaldehyde with 4-dimethylaminobenzohydrazide in methanol. The Schiff base molecule is approximately planar, with a mean deviation from the least-squares plane defined by the non-H atoms of 0.0452 (3) Å, and with a dihedral angle between the benzene rings of 4.2 (3)°. This planarity is assisted by the formation of an intramolecular O—H⋯N hydrogen bond. In the crystal, adjacent Schiff base molecules are linked by two methanol molecules through N—H⋯O and O—H⋯O hydrogen bonds, forming dimers.

Related literature

For the preparation of Schiff base compounds by the condensation reaction between aldehydes with organic primary amines, see: Miura et al. (2009 ▶); Zhao et al. (2010 ▶); Karadağ et al. (2011) ▶; Bingöl Alpaslan et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₅Cl₂N₃O₂·CH₄O
M _r = 384.25
Monoclinic,
a = 7.6498 (15) Å
b = 14.338 (3) Å
c = 16.884 (2) Å
β = 103.076 (2)°
V = 1803.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 298 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.952, T _max = 0.963
8311 measured reflections
3238 independent reflections
1790 reflections with I > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.180
S = 1.03
3238 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010148/qm2057sup1.cif

e-68-o1042-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010148/qm2057Isup2.hkl

e-68-o1042-Isup2.hkl^{(158.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010148/qm2057Isup3.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
N2—H2⋯O3ⁱ	0.86	2.10	2.848 (5)	145
O1—H1⋯N1	0.82	1.91	2.600 (5)	141
O3—H3⋯O2	0.82	1.97	2.771 (5)	166

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The condensation reaction between aldehydes with organic primary amines readily forms Schiff bases containing the typical –C=N– groups (Miura et al., 2009; Zhao et al., 2010; Karadağ et al., 2011; Bingöl Alpaslan et al., 2010). In this paper, the new title compound (Fig. 1), was prepared by the reaction of 3,5-dichlorosalicylaldehyde with 4-dimethylaminobenzohydrazide in methanol.

The asymmetric unit comprises a Schiff base molecule and a methanol molecule. The Schiff base molecule is approximately planar, with mean deviation from the least squares plane defined by the non-hydrogen atoms of 0.0452 (3) Å, and with the dihedral angle between the two benzene rings of 4.2 (3)°. This planarity is assisted by the formation of an intramolecular O1—H1···N1 hydrogen bond (Table 1). All the bond lengths are within normal ranges (Allen et al., 1987). In the crystal structure adjacent Schiff base molecules are linked by two methanol molecules through intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) to form a dimer (Fig. 2).

Experimental

3,5-Dichlorosalicylaldehyde (1.0 mmol, 0.190 g) and 4-dimethylaminobenzohydrazide (1.0 mmol, 0.179 g) were refluxed for 30 min in 30 ml me thanol, and cooled to room temperature to give colorless solid, which was isoloated by filtration. Single crystals of the title compound were formed by recrystallization of the solid product in methanol.