(E)-N′-(4-Methoxy­benzyl­idene)benzohydrazide

Jian-Xia Gou; Ming-Zhi Song; Chuan-Gang Fan; Zhong-Nian Yang

doi:10.1107/S1600536809049988

. 2009 Nov 25;65(Pt 12):o3207. doi: 10.1107/S1600536809049988

(E)-N′-(4-Methoxybenzylidene)benzohydrazide

Jian-Xia Gou ^a, Ming-Zhi Song ^a,^b, Chuan-Gang Fan ^a,^*, Zhong-Nian Yang ^a

PMCID: PMC2972045 PMID: 21578915

Abstract

In the title molecule, C₁₅H₁₄N₂O₂, the dihedral angle between the benzene rings is 5.93 (17)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains propagating in [010].

Related literature

For properties of Schiff base ligands, see: Cozzi et al. (2004 ▶). For related crystal structures, see: Fun et al. (2008 ▶); Cui et al. (2009 ▶); Nie (2008 ▶). graphic file with name e-65-o3207-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M _r = 254.28
Orthorhombic,
a = 31.414 (3) Å
b = 5.1067 (5) Å
c = 8.1336 (9) Å
V = 1304.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.49 × 0.48 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.958, T _max = 0.974
2220 measured reflections
1239 independent reflections
920 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.106
S = 1.03
1239 reflections
173 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049988/bq2172sup1.cif

e-65-o3207-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049988/bq2172Isup2.hkl

e-65-o3207-Isup2.hkl^{(60KB, 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
N1—H1⋯O1ⁱ	0.86	2.17	2.961 (2)	152

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the financial support of the Foundation of Binzhou University.

supplementary crystallographic information

Comment

Schiff bases are popular ligands in coordination chemistry due to their ease of synthesis and their ability to be readily modified both electronically and sterically. Mixed-donor Schiff bases have been used extensively in catalysis (Cozzi, 2004).

In (I), (Fig. 1), the bond lengths an angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Cui et al., 2009).

In the crystal structure, the C8=N2 bond length in the molecule is 1.269 (3) °, showing the double-bond character. Meanwhile, the dihedral angle between the benzene ring (C2-C7) and the benzene ring (C9-C14) in the Schiff base molecule is 5.93 (17) °, indicating that the two aromatic ring planes are almost coplanar. Moreover, the crystal supramolecular structure was built from the connections of weak intermolecular N—H···O hydrogen bonds, as shown in table 1, and these hydrogen bonds link molecules into one-dimensional chains propagated in direction [010].

Experimental

Benzohydrazide (5.0 mmol), 20 ml ethanol and 4-methoxybenzaldehyde (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₁₅H₁₄N₂O₂: C 70.85, H 5.55, N 11.02%; found: C 70.78, H 5.64, N 11.13%.