N′-[4-(Dimethyl­amino)benzyl­idene]acetohydrazide

Wei-Wei Li; Tie-Ming Yu; Wen-Bo Yu; Lu-Ping Lv; Xian-Chao Hu

doi:10.1107/S1600536809032619

. 2009 Aug 22;65(Pt 9):o2197. doi: 10.1107/S1600536809032619

N′-[4-(Dimethylamino)benzylidene]acetohydrazide

Wei-Wei Li ^a, Tie-Ming Yu ^a, Wen-Bo Yu ^a, Lu-Ping Lv ^a, Xian-Chao Hu ^b,^*

PMCID: PMC2969918 PMID: 21577600

Abstract

The title compound, C₁₁H₁₅N₃O, crystallizes with two independent molecules per asymmetric unit which differ slightly in their side-chain orientations: the C=N—N—C torsion angle is −176.2 (3)° in one of the molecules and −179.83 (3)° in the other. Each independent molecule adopts a trans configuration with respect to the C=N bond. The two independent molecules are related by a pseudo-inversion center and they exist as a N—H⋯O hydrogen-bonded dimer. The dimers are linked into zigzag chains along [100] by C—H⋯O hydrogen bonds.

Related literature

For general background to this type of compound, see: Cimerman et al. (1997 ▶); Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For related structures, see: Li & Jian (2008 ▶); Shang et al. (2007 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C₁₁H₁₅N₃O
M _r = 205.26
Orthorhombic,
a = 8.619 (4) Å
b = 20.063 (3) Å
c = 26.231 (3) Å
V = 4536 (2) Å³
Z = 16
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 223 K
0.25 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.977, T _max = 0.979
25277 measured reflections
3944 independent reflections
2266 reflections with I > 2σ(I)
R _int = 0.086

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.260
S = 1.05
3944 reflections
278 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 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/S1600536809032619/ci2860sup1.cif

e-65-o2197-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032619/ci2860Isup2.hkl

e-65-o2197-Isup2.hkl^{(189.5KB, 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⋯O2ⁱ	0.86	2.09	2.930 (4)	166
N6—H6⋯O1ⁱⁱ	0.86	2.04	2.884 (4)	165
C3—H3⋯O1ⁱⁱⁱ	0.93	2.56	3.328 (4)	140

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

Acknowledgments

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) and Hangzhou Vocational and Technical College for financial support.

supplementary crystallographic information

Comment

Schiff bases have attracted much attention due to the possibility of their analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and as 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 (Fig. 1).

The title compound contains two independent, but almost identical molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. The N1/N2/O1/C9/C10/C11 and N5/N6/O2/C10/C21/C22 planes form dihedral angles of 4.68 (6)° and 6.93 (5)°, respectively, with the C3-C8 and C14-C19 planes. The dihedral angle between the two independent benzene rings is 88.26 (9)°. Bond lengths and angles are comparable to those observed for related structures (Li et al., 2008; Shang et al., 2007).

The two independent molecules are related by a pseudo inversion center, and in the crystal they exist as N—H···O hydrogen-bonded dimers. The dimers are linked into a zigzag chain along the 'a' axis by C—H···O hydrogen bonds. (Table 1).

Experimental

4-Dimethylaminobenzaldehyde (1.49 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 3.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 87% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 490–493 K).