(Z)-4-[(3-Aminona­phthalen-2-yl­amino)(phen­yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Zhao Zhang; Xingqiang Lü; Shunsheng Zhao; Xiangrong Liu

doi:10.1107/S1600536812034770

. 2012 Aug 25;68(Pt 9):o2777. doi: 10.1107/S1600536812034770

(Z)-4-[(3-Aminonaphthalen-2-ylamino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Zhao Zhang ^a, Xingqiang Lü ^a, Shunsheng Zhao ^b, Xiangrong Liu ^b,^*

PMCID: PMC3435809 PMID: 22969655

Abstract

The molecule of the title compound, C₂₇H₂₂N₄O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 12.73 (11), 65.17 (6) and 49.82 (6)°, respectively, with the two benzene rings and the naphthalene ring system. In the crystal, pairs of molecules are linked by intermolecular N—H⋯N hydrogen bonds, forming dimers. The secondary amino group is involved in an intramolecular N—H⋯O hydrogen bond.

Related literature

For a related structure, see: Lu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the synthesis, see: Hennig & Mann (1988 ▶).

Experimental

Crystal data

C₂₇H₂₂N₄O
M _r = 418.49
Monoclinic,
a = 9.8052 (14) Å
b = 18.041 (3) Å
c = 13.2193 (18) Å
β = 110.797 (2)°
V = 2186.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.31 × 0.25 × 0.24 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.976, T _max = 0.981
10878 measured reflections
3886 independent reflections
2629 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.123
S = 1.07
3886 reflections
290 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536812034770/ff2079sup1.cif

e-68-o2777-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034770/ff2079Isup2.hkl

e-68-o2777-Isup2.hkl^{(190.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034770/ff2079Isup3.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
N3—H3A⋯O1	0.86	2.06	2.7196 (19)	133
N4—H4A⋯N2ⁱ	0.92 (2)	2.21 (2)	3.121 (2)	169.8 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The project was supported by the National Natural Science Foundation of China (program Nos. 21103135, 21073139), the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2011JQ2011) and the Scientific Research Program Funded by Shaanxi Provincial Education Department (program No.12 J K0622).

supplementary crystallographic information

Comment

Asymmetric Schiff bases attract the interest of researchers because they can form complexes with most of transition metal ions. These Schiff base complexes show excellent catalytic activity and selectivity in various reactions. Here we report the crystal structure of a novel asymmetrical Schiff base ligand (I) (Fig. 1). Bond lengths are in the range of normal values (Allen et al., 1987) and are comparable to those observed in similar compounds (Lu et al., 2011). The molecules of the title compound are linked by N—H···N hydrogen to form molecular pairs (Fig. 2). An intramolecular N3—H3a···O1 hydrogen bond forms an S6 ring motif.

Experimental

The title compound was obtained according to the synthetic procedure of Hennig & Mann (1988) with some modification. 2,3-diaminonaphthalene and 4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one were refluxed for 2 h in a molar ratio of 1:1 in absolute ethanol to give the product. The single-crystal of suitable for X-ray diffraction was obtained by slow evaporation of its ethanolic solution of the title compound.