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

Rong Lu; Hua Xia; Xingqiang Lü; Shunsheng Zhao

doi:10.1107/S1600536811037470

. 2011 Sep 30;67(Pt 10):o2701. doi: 10.1107/S1600536811037470

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

Rong Lu ^a,^*, Hua Xia ^a, Xingqiang Lü ^a, Shunsheng Zhao ^b

PMCID: PMC3201420 PMID: 22065632

Abstract

The molecule of the title compound, C₂₃H₂₀N₄O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 10.33 (11), 65.34 (11) and 63.52 (10)° with the three benzene rings. In the crystal, the molecules are linked by intermolecular N—H⋯N hydrogen bonds, generating chains parallel to the b axis. The secondary amino group is involved in an intramolecular N—H⋯O hydrogen bond.

Related literature

For the synthesis, properties and applications of the title compound, see: Hennig & Mann (1988 ▶); Bao et al. (2005 ▶).

Experimental

Crystal data

C₂₃H₂₀N₄O
M _r = 368.43
Monoclinic,
a = 9.200 (2) Å
b = 21.680 (5) Å
c = 9.608 (2) Å
β = 97.840 (4)°
V = 1898.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.857, T _max = 1.000
9447 measured reflections
3369 independent reflections
1983 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.119
S = 0.94
3369 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 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 and local programs.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037470/fy2020sup1.cif

e-67-o2701-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037470/fy2020Isup2.hkl

e-67-o2701-Isup2.hkl^{(165.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037470/fy2020Isup3.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—H1C⋯O1	0.96 (2)	1.93 (2)	2.733 (2)	139.8 (16)
N4—H4B⋯N2ⁱ	0.86	2.34	3.194 (2)	173
N4—H4A⋯N2ⁱⁱ	0.86	2.50	3.209 (2)	140

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

Acknowledgments

This project was supported by the Natural Science Basic Research Plan in Shaanxi Province of China (program Nos 2010JM2006 and 2011JQ2011) and the Scientific Research Program funded by the Shaanxi Provincial Education Department (program No. 2008 J K440).

supplementary crystallographic information

Comment

The molecules of the title compound (Fig. 1) are linked by N—H···N hydrogen bonds, generating parallel chains as shown in Fig. 2. The aminophenyl rings protrude on both sides of these chains. Adjacent chains are linked by stacking interactions between the protruding rings. The distance between the ring centroids is 3.6953 (14) Å.

Experimental

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