2-[2-(2-Carb­oxy­phen­yl)hydrazinyl­idene]-3-oxo-N-phenyl­butyramide

Jinlong Dong; Gailing Zhang; Meiyu Guo; Chuan Wu; Jianguo Ren

doi:10.1107/S1600536811048173

. 2011 Nov 23;67(Pt 12):o3408. doi: 10.1107/S1600536811048173

2-[2-(2-Carboxyphenyl)hydrazinylidene]-3-oxo-N-phenylbutyramide

Jinlong Dong ^a, Gailing Zhang ^a, Meiyu Guo ^a, Chuan Wu ^b, Jianguo Ren ^b,^*

PMCID: PMC3239046 PMID: 22199894

Abstract

In the title compound, C₁₇H₁₅N₃O₄, the molecule is in the keto–hydrazone form. Intramolecular N—H⋯O hydrogen bonds ensure that the molecule is nearly planar (r.m.s. deviation of non-H atoms is 0.098 Å), with the two benzene rings forming a dihedral angle of 10.04 (2)°. In the crystal, inversion dimers are formed via pairs of O—H⋯O hydrogen bonds involving the –CO₂H groups.

Related literature

For general background to the properties of organic pigments, see: Schmidt et al. (2007 ▶); Barrow et al. (2002 ▶). For related structures, see: van de Streek et al. (2009 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₅N₃O₄
M _r = 325.32
Monoclinic,
a = 15.5731 (16) Å
b = 5.3292 (5) Å
c = 18.7731 (19) Å
β = 99.246 (1)°
V = 1537.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.50 × 0.30 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.951, T _max = 0.979
7277 measured reflections
2724 independent reflections
1459 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.137
S = 1.02
2724 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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) I, global. DOI: 10.1107/S1600536811048173/pk2357sup1.cif

e-67-o3408-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048173/pk2357Isup2.hkl

e-67-o3408-Isup2.hkl^{(133.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811048173/pk2357Isup3.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
O4—H4⋯O3ⁱ	0.82	1.84	2.654 (3)	175
N3—H3⋯O1	0.86	1.97	2.685 (3)	140
N1—H1⋯O3	0.86	1.99	2.631 (3)	131
N1—H1⋯O2	0.86	1.91	2.568 (3)	132

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge the University Technology Development Project in Shanxi Province (grant No. 20111122).

supplementary crystallographic information

Comment

Organic pigments are nowadays most commonly used for coloring paints and plastics and for most printing applications (Schmidt et al., 2007; Barrow et al., 2002). Originally, azo pigments were believed to contain the azo group N═N, but for approximately 25 years now it has been known that all Hansa yellow pigments (and all other commercial 'azo' pigments) crystallize in the hydrazone form; it would, therefore, be more appropriate to speak of 'hydrazone' pigments (van de Streek et al., 2009). In this paper, we present the crystal structure of the title hydrazone compound (I). The molecular structure of (I) is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are normal. The O2—C4 (1.226 (3) Å) and N3—C4 (1.343 (3) Å) distances are consistent with the keto form of the amide functionality. The N1—N2 (1.310 (3) Å) and N2—C3(1.306 (3) Å) distances are consistent with hydrazone form functionality.

Experimental

To a sodium hydroxide solution (20 cm³) of acetoacetanilide (102 mmol), 40 cm³ (101 mmol) diazcompound of o-aminobenzoic acid was added and the mixture was heated to 90° for 1 h. A yellow solid separated and was collected by filtration, washed with diethyl ether (absolute) and dried in air. Then the precipitate was dissolved in methanol and the solution was allowed to stand for a few days at ambient temperature, after which time yellow blocky crystals of the title compound suitable for X-ray diffraction were obtained.