N′-[4-(Dimethyl­amino)benzyl­idene]-3-hydroxy­benzohydrazide

Yi Nie

doi:10.1107/S160053680800130X

. 2008 Jan 18;64(Pt 2):o471. doi: 10.1107/S160053680800130X

N′-[4-(Dimethylamino)benzylidene]-3-hydroxybenzohydrazide

Yi Nie ^a,^*

PMCID: PMC2960467 PMID: 21201497

Abstract

The title compound, C₁₆H₁₇N₃O₂, was synthesized by the reaction of 4-dimethylaminobenzaldehyde with 3-hydroxybenzoic acid hydrazide in methanol. The dihedral angle between the two benzene rings in the molecule is 9.2 (2)°. In the crystal structure, molecules are linked through intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For related literature, see: Akitsu & Einaga (2006 ▶); Bahner et al. (1968 ▶); Butcher et al. (2005 ▶); Hodnett & Mooney (1970 ▶); Merchant & Chothia (1970 ▶); Pradeep (2005 ▶); Sigman & Jacobsen (1998 ▶).

Experimental

Crystal data

C₁₆H₁₇N₃O₂
M _r = 283.33
Monoclinic,
a = 13.397 (3) Å
b = 9.663 (2) Å
c = 11.183 (2) Å
β = 101.97 (3)°
V = 1416.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.28 × 0.27 × 0.27 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.975, T _max = 0.976
11531 measured reflections
3094 independent reflections
2579 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.130
S = 1.05
3094 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800130X/su2040sup1.cif

e-64-0o471-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800130X/su2040Isup2.hkl

e-64-0o471-Isup2.hkl^{(151.8KB, 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
O2—H2⋯O1ⁱ	0.82	2.18	2.8470 (14)	138
O2—H2⋯N2ⁱ	0.82	2.36	3.1008 (16)	150
N3—H3A⋯O1ⁱⁱ	0.895 (9)	2.561 (11)	3.4172 (16)	160.4 (16)

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

Schiff base compounds have been widely investigated due to their easy synthesis, versatile structures and wide applications (Sigman & Jacobsen, 1998; Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005). The excellent antibacterial and antitumor properties of such compounds have attracted much interest in recent years (Hodnett & Mooney, 1970; Bahner et al., 1968; Merchant & Chothia, 1970). In order to investigate further the structures of such compounds, the new title Schiff base compound is reported on here.

The dihedral angle between the two benzene rings in the molecule (Fig. 1) of the title compound is 9.2 (2)°. In the crystal structure, molecules are linked through intermolecular O–H···O, O–H···N and N–H···O hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).

Experimental

The title compound was obtained by stirring of 4-dimethylaminobenzaldehyde (0.1 mmol, 14.9 mg) and 3-hydroxybenzoic acid hydrazide (0.1 mmol, 15.2 mg) in a methanol solution (10 ml) at room temperature. Yellow block-shaped single crystals suitable for X-ray diffraction were formed from the solution after seven days.