N′-(4-Diethyl­amino-2-hy­droxy­benzyl­idene)-4-(dimethyl­amino)­benzo­hydrazide methanol monosolvate

Fu Su; Zheng-Gui Gu; Jun Lin

doi:10.1107/S1600536811019957

. 2011 Jun 11;67(Pt 7):o1634. doi: 10.1107/S1600536811019957

N′-(4-Diethylamino-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate

Fu Su ^a, Zheng-Gui Gu ^a, Jun Lin ^a,^*

PMCID: PMC3151952 PMID: 21837040

Abstract

The title compound, C₂₀H₂₆N₄O₂·CH₃OH, was prepared by the reaction of 4-diethylamino-2-hydroxybenzaldehyde with 4-(dimethylamino)benzohydrazide. The dihedral angle between the two benzene rings is 13.6 (3)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, the hydrazone and methanol molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds, forming chains along a.

Related literature

For the biological properties of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For similar structures, see: Huang & Wu (2010 ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₀H₂₆N₄O₂·CH₄O
M _r = 386.49
Triclinic,
a = 6.786 (3) Å
b = 11.791 (3) Å
c = 14.252 (2) Å
α = 111.511 (3)°
β = 92.811 (2)°
γ = 96.492 (2)°
V = 1049.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.27 × 0.23 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.978, T _max = 0.983
7543 measured reflections
4421 independent reflections
1809 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.189
S = 1.00
4421 reflections
263 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 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/S1600536811019957/sj5154sup1.cif

e-67-o1634-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019957/sj5154Isup2.hkl

e-67-o1634-Isup2.hkl^{(216.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811019957/sj5154Isup3.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⋯O3	0.90 (1)	2.07 (2)	2.936 (4)	160 (3)
O3—H3⋯O2ⁱ	0.82	1.84	2.661 (3)	177
O1—H1⋯N1	0.82	2.02	2.727 (3)	145

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge the project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

supplementary crystallographic information

Comment

In the last year, much attention has been focused on the biological properties of hydrazone compounds (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). The crystal structures of a number of hydrazone compounds have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). In this paper, the title new hydrazone compound, Fig. 1, is reported.

The asymmetric unit of the compound contains a hydrazone molecule and a methanol molecule. The dihedral angle between the two benzene rings is 13.6 (3)° and an intramolecular O1—H1···N1 hydrogen bond forms an S(6) ring (Bernstein et al., 1995). In the crystal structure, the hydrazone and methanol molecules are linked through intermolecular O–H···O and N–H···O hydrogen bonds (Table 1), to form 1D chains along a (Fig. 2).

Experimental

The reaction of 4-diethylamino-2-hydroxybenzaldehyde (0.193 g, 1 mmol) with 4-(dimethylamino)benzohydrazide (0.179 g, 1 mmol) in 30 ml methanol at room temperature afforded the title compound. Colorless single crystals were formed by gradual evaporation of the solution in air.