(E)-N′-(5-Bromo-2-hy­droxy­benzyl­idene)-4-(dimethyl­amino)­benzohydrazide

En-Yu Wei

doi:10.1107/S1600536812013785

. 2012 Apr 4;68(Pt 5):o1304. doi: 10.1107/S1600536812013785

(E)-N′-(5-Bromo-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide

En-Yu Wei ^a,^*

PMCID: PMC3344449 PMID: 22590211

Abstract

The title compound, C₁₆H₁₆BrN₃O₂, crystallized with two independent molcules in the asymmetric unit. Each molecule has an E conformation about the C=N bond and the dihedral angles between the benzene rings are 30.5 (3) and 28.7 (3)°. In each molecule, there is an O—H⋯N hydrogen bond and the two molecules are linked by an N—H⋯O hydrogen bond. In the crystal, molecules are further linked via N—H⋯O hydrogen bonds into chains propagating along [001].

Related literature

For further details concerning benzohydrazone compounds, see: Wang et al. (2012 ▶); Horkaew et al. (2012 ▶); Li (2011a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C₁₆H₁₆BrN₃O₂
M _r = 362.23
Monoclinic,
a = 35.3800 (12) Å
b = 10.452 (1) Å
c = 18.5070 (15) Å
β = 111.463 (2)°
V = 6369.1 (8) Å³
Z = 16
Mo Kα radiation
μ = 2.59 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.625, T _max = 0.653
25287 measured reflections
6931 independent reflections
2320 reflections with I > 2σ(I)
R _int = 0.168

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.197
S = 0.94
6931 reflections
411 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812013785/su2400sup1.cif

e-68-o1304-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013785/su2400Isup2.hkl

e-68-o1304-Isup2.hkl^{(339.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013785/su2400Isup3.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
O1—H1⋯N1	0.85 (1)	1.78 (3)	2.570 (7)	153 (7)
O3—H3A⋯N4	0.82	1.87	2.588 (7)	146
N2—H2⋯O4	0.90 (1)	2.04 (2)	2.920 (6)	166 (6)
N5—H5⋯O2ⁱ	0.90 (1)	1.95 (3)	2.807 (7)	160 (6)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author is grateful to the Zibo Vocational Institute for supporting this work.

supplementary crystallographic information

Comment

Continuing our work on the preparation (E)-N'-(5-Bromo-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazideof benzohydrazone compounds, the new title compound was synthesized and we report herein on its crystal structure.

The asymmetric unit of the title compound contains two independent molecules (A and B), Fig. 1. Each molecule has an E conformation about the C═N bond. In molecule A the dihedral angle between the C1–C6 and C9–C14 benzene rings is 30.5 (3)°. In molecule B the dihedral angle between the benzene rings C17–C22 and C25–C30 is 28.7 (3)°. The bond lengths are within normal values when compared with those observed in the similar compounds (Wang et al., 2012; Horkaew et al., 2012; Li, 2011a,b; Li, 2012). In each molecule there is an O-H···N hydrogen bond , and the two indpendent molecules are linked by an N-H···O hydrogen bond (Table 1 and Fig. 1).

In the crystal, molecules are linked through N–H···O hydrogen bonds to form chains propagating along the c axis direction (Table 1 and Fig. 2).

Experimental

A mixture of 5-bromosalicylaldehyde (0.201 g, 1 mmol) and 4-dimethylaminobenzohydrazide (0.179 g, 1 mmol), and a few drops of acetic acid, were mixed and refluxed in 20 ml ethanol for 30 min. The reaction mixture was then cooled slowly to room temperature. Colourless block-like crystals of the title compound, suitable for X-ray analysis, were formed by slow evaporation of the solution.