N′-(4-Diethyl­amino-2-hy­droxy­benzyl­idene)-4-methyl­benzohydrazide

Xi-Hai Shen; Li-Juen Shao; Zhao-Fu Zhu; Li-Xue Zhu

doi:10.1107/S1600536812010690

. 2012 Mar 17;68(Pt 4):o1078. doi: 10.1107/S1600536812010690

N′-(4-Diethylamino-2-hydroxybenzylidene)-4-methylbenzohydrazide

Xi-Hai Shen ^a, Li-Juen Shao ^a, Zhao-Fu Zhu ^a,^*, Li-Xue Zhu ^a

PMCID: PMC3344033 PMID: 22589942

Abstract

The title compound, C₁₉H₂₃N₃O₂, was prepared by condensing 4-diethylamino-2-hydroxybenzaldehyde and 4-methylbenzohydrazide in methanol. The asymmetric unit contains two independent molecules in which the two benzene rings make dihedral angles of 30.3 (3) and 18.9 (3)°. Intramolecular O—H⋯N hydrogen bonds are observed in both molecules. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which form chains along the a axis.

Related literature

For the structures of similar hydrazone compounds, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Zhi et al. (2011 ▶); Huang & Wu (2010 ▶); Shen et al. (2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₂₃N₃O₂
M _r = 325.40
Triclinic,
a = 9.923 (2) Å
b = 11.963 (2) Å
c = 15.827 (2) Å
α = 95.269 (2)°
β = 98.932 (2)°
γ = 103.691 (2)°
V = 1787.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.990, T _max = 0.994
13230 measured reflections
6512 independent reflections
1651 reflections with I > 2σ(I)
R _int = 0.137

Refinement

R[F ² > 2σ(F ²)] = 0.086
wR(F ²) = 0.245
S = 0.85
6512 reflections
449 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 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/S1600536812010690/sj5209sup1.cif

e-68-o1078-sup1.cif^{(35.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010690/sj5209Isup2.hkl

e-68-o1078-Isup2.hkl^{(318.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010690/sj5209Isup3.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⋯O4ⁱ	0.90 (1)	1.95 (2)	2.831 (7)	167 (6)
O1—H1⋯N1	0.82	1.93	2.641 (7)	145
N5—H5⋯O2	0.90 (1)	2.12 (2)	2.985 (7)	160 (6)
O3—H3⋯N4	0.85 (1)	1.94 (1)	2.581 (7)	132 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

In the last few years, a number of hydrazone compounds have been reported (Fun et al., 2011; Horkaew et al., 2011; Zhi et al., 2011; Huang & Wu, 2010). As an extension of our work on such compounds (Shen et al., 2012), we report here the structure of a new benzohydrazide compound, (I).

The asymmetric unit of the compound contains two independent molecules (Fig.1) both of which form intramolecular O—H···N hydrogen bonds (Table 1). The dihedral angle between the C7-N1-N2-C8-O2 plane and the C1—C6 benzene ring is 15.4 (2)° while that between the C26-N4-N5-C27-O4 section of the molecule and the C20—C25 benzene ring is 5.8 (2)°. The planarity of these portions of the molecule may result from the formation of intramolecular O—H···N hydrogen bonds. All the bond distances are within normal ranges (Allen et al., 1987) and comparable with those in the similar compounds reported recently and mentioned previously. The crystal structure of the compound is stabilized by intermolecular N—H···O hydrogen bonds, to form chains along the a axis (Table 1, Fig. 2).

Experimental

2-Hydroxy-4-diethylaminobenzaldehyde (193.0 mg, 1.0 mmol) and 4-methylbenzohydrazide (150.1 mg, 1.0 mmol) were mixed in methanol (60 ml). The mixture was refluxed for 30 min, then cooled to room temperature, yielding a colorless solution. Small, colorless crystals were formed when the solution was evaporated in air for several days.