N′-[4-(Dimethyl­amino)­benzyl­idene]-4-meth­oxybenzohydrazide

Jiu-Fu Lu

doi:10.1107/S1600536808031012

. 2008 Sep 30;64(Pt 10):o2033. doi: 10.1107/S1600536808031012

N′-[4-(Dimethylamino)benzylidene]-4-methoxybenzohydrazide

Jiu-Fu Lu ^a,^*

PMCID: PMC2959335 PMID: 21201227

Abstract

The title Schiff base compound, C₁₇H₁₉N₃O₂, was obtained from the condensation of 4-dimethylaminobenzaldehyde with 4-methoxybenzohydrazide in an ethanol solution. The molecule is twisted with respect to the N—N single bond [C—N—N—C = −159.27 (14)°] and the dihedral angle between the two aromatic rings is 67.1 (2)°. In the crystal structure, the molecules are linked into chains along the c axis by intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Nie (2008 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₉N₃O₂
M _r = 297.35
Monoclinic,
a = 11.922 (4) Å
b = 13.224 (5) Å
c = 9.756 (4) Å
β = 91.469 (6)°
V = 1537.6 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.23 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.981, T _max = 0.983
8744 measured reflections
3296 independent reflections
2507 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.121
S = 1.03
3296 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031012/ci2684sup1.cif

e-64-o2033-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031012/ci2684Isup2.hkl

e-64-o2033-Isup2.hkl^{(161.7KB, 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
N2—H2A⋯O1ⁱ	0.90 (1)	1.99 (1)	2.873 (2)	167 (2)
C7—H7⋯O1ⁱ	0.93	2.54	3.297 (2)	139

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks the Scientific Research Foundation of Shaanxi University of Technology for financial support (project No. SLGQD0708).

supplementary crystallographic information

Comment

As part of our investigation of the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report here the crystal structure of the title new Schiff base compound.

In the title molecule (Fig. 1), the bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 67.1 (2)°, indicating that the molecule is twisted. The methoxy group is coplanar with the attached ring [C15—O2—C12—C13 = 0.8 (2)°]. The dimethylamino group is almost coplanar with the attached ring [C16—N3—C1—C2 = 3.8 (2)° and C17—N3—C1—C6 = 8.7 (3)°]. The C7–N1—N2—C8 torsion angle [-159.27 (14)°] indicates that the molecule is twisted about the N1—N2 bond.

In the crystal structure, the molecules are linked into chains (Fig. 2) running along the c axis by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1).

Experimental

The title compound was prepared by the Schiff base condensation of 4-dimethylaminobenzaldehyde (0.1 mol) and 4-methoxybenzohydrazide (0.1 mol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a 95% ethanol solution at room temperature.