N′-(3,4-Dimethoxy­benzyl­idene)aceto­hydrazide

Bao-Cheng Zhou; Lu-Ping Lv; Wen-Bo Yu; Wei-Wei Li; Xian-Chao Hu

doi:10.1107/S1600536809028608

. 2009 Jul 25;65(Pt 8):o1964. doi: 10.1107/S1600536809028608

N′-(3,4-Dimethoxybenzylidene)acetohydrazide

Bao-Cheng Zhou ^a,^b,^*, Lu-Ping Lv ^c, Wen-Bo Yu ^c, Wei-Wei Li ^c, Xian-Chao Hu ^d

PMCID: PMC2977217 PMID: 21583641

Abstract

The asymmetric unit of the title compound, C₁₁H₁₄N₂O₃, contains two independent molecules with close conformations; the C=N—N—C torsion angle is 176.4 (1)° in both molecules. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains running along the [01 Inline graphic ] direction.

Related literature

For general background to the applications of Schiff bases, see: Cimerman et al. (1997 ▶); Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For related structures, see: Li & Jian (2008 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C₁₁H₁₄N₂O₃
M _r = 222.24
Triclinic,
a = 8.339 (3) Å
b = 8.349 (3) Å
c = 8.663 (3) Å
α = 94.717 (12)°
β = 95.210 (8)°
γ = 94.298 (12)°
V = 596.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 223 K
0.24 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.987, T _max = 0.990
3236 measured reflections
2054 independent reflections
1890 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.110
S = 1.12
2054 reflections
290 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536809028608/cv2586sup1.cif

e-65-o1964-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028608/cv2586Isup2.hkl

e-65-o1964-Isup2.hkl^{(98.9KB, 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—H2⋯O4ⁱ	0.86	2.11	2.950 (3)	165
N2—H2⋯O5ⁱ	0.86	2.54	3.154 (3)	129
C7—H7⋯O6	0.93	2.52	3.372 (3)	152
C12—H12B⋯O3ⁱⁱ	0.96	2.51	3.434 (4)	162
C12—H12C⋯O6ⁱⁱⁱ	0.96	2.45	3.367 (4)	159
C16—H18⋯O2^iv	0.93	2.45	3.244 (3)	144
N4—H4⋯O3^v	0.86	2.08	2.907 (3)	161

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors thank Zhejiang Sci-tech University and the Science and Technology Project of Zhejiang Province for financial support (grant No. 2007 F70077) .

supplementary crystallographic information

Comment

Schiff bases have attracted much attention due to their possible analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952; Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound.

The title compound (Fig. 1) crystallizes with two independent molecules in the asymmetric unit. The side chains in the two independent molecules have the same orientations, with the C═N—N—C torsion angle being 176.4 (1)° in both molecules. The N1/N2//O3/C9/C10/C11 and N3/N4/O6/C20/C21/C22 planes form dihedral angles of 6.00 (5)° and 4.38 (9)°, respectively, with the C2—C7 and C13—C18 planes. The dihedral angle between the two independent benzene rings is 79.39 (7)°. The bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li et al., 2008).

In the crystal structure, the molecules are linked into chains running along the [01-1] by N—H···O and C—H···O hydrogen bonds(Table 1).

Experimental

3,4-Methoxybenzaldehyde (1.66 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (25 ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 85% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 468–470 K).