3-Bromo-N′-[(2-meth­oxy­naphthalen-1-yl)methyl­idene]benzohydrazide

He-Bing Li

doi:10.1107/S1600536811019349

. 2011 May 28;67(Pt 6):o1532. doi: 10.1107/S1600536811019349

3-Bromo-N′-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide

He-Bing Li ^a,^*

PMCID: PMC3120542 PMID: 21754892

Abstract

The molecule of the title compound, C₁₉H₁₅BrN₂O₂, displays a pseudo-trans conformation about the N—N bond [C—N—N=C torsion angle = 164.7 (2)°]. The dihedral angle between the planes of the benzene ring and the naphthyl system is 70.1 (2)°. In the crystal, molecules are linked into C(4) chains along the c axis by N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Li (2007a ▶,b ▶, 2008 ▶); Qiu et al. (2006 ▶); Yang & Guo (2006 ▶); Yang (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₁₅BrN₂O₂
M _r = 383.24
Monoclinic,
a = 12.3562 (11) Å
b = 17.0404 (15) Å
c = 8.6175 (10) Å
β = 110.155 (2)°
V = 1703.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.43 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.530, T _max = 0.560
9533 measured reflections
3513 independent reflections
1721 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.132
S = 1.00
3513 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 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 datablocks global, I. DOI: 10.1107/S1600536811019349/hb5889sup1.cif

e-67-o1532-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019349/hb5889Isup2.hkl

e-67-o1532-Isup2.hkl^{(172.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811019349/hb5889Isup3.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⋯O2ⁱ	0.90 (1)	2.10 (1)	2.989 (5)	174 (5)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges a research grant from Xiangnan University.

supplementary crystallographic information

Comment

In the last few years, the author has reported the sturctures of various hydrazone compounds (Li, 2008; Li, 2007a,b). As an extension of work on the structures of such compounds, the title new hydrazone compound is reported.

The bond lengths and bond angles in the title compound (Fig. 1) are within normal ranges (Allen et al., 1987) and comprable with those observed in similar compounds (Qiu et al., 2006; Yang & Guo, 2006; Yang, 2006). The dihedral angle between the C1—C10 naphthyl ring and C14—C19 benzene ring is 70.1 (2)°. The molecule of the compound adopts a trans configuration about the C12═N1 and C13—N2 bonds. In the crystal structure, the molecules are linked into chains along the c axis by N—H···O hydrogen bonds (Table 1 and Fig.2).

Experimental

2-Methoxy-1-naphthaldehyde (0.1 mmol, 18.6 mg) and 3-bromobenzohydrazide (0.1 mmol, 21.5 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min to give a clear colorless solution. Colourless blocks of (I) were formed by gradual evaporation of the solvent over a week at room temperature (yield 63%).