(4Z)-4-[(Cyclo­propyl­amino)(phen­yl)methyl­ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Hai-Zhen Xu; Yan-Xia Yang; You-Quan Zhu

doi:10.1107/S1600536810013723

. 2010 Apr 21;66(Pt 5):o1123. doi: 10.1107/S1600536810013723

(4Z)-4-[(Cyclopropylamino)(phenyl)methylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Hai-Zhen Xu ^a,^*, Yan-Xia Yang ^b, You-Quan Zhu ^c,^*

PMCID: PMC2979282 PMID: 21579173

Abstract

In the title compound, C₂₀H₁₉N₃O, the dihedral angles formed by the pyrazolone ring with the two phenyl rings are 64.27 (6) and 17.00 (6)°. The molecular structure is stabilized by intramolecular N—H⋯O and C—H⋯O hydrogen bonds. In the crystal, the molecules are linked into chains along the b axis by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the antibacterial, biological and analgesic activity of metal complexes of 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one, see: Li et al. (1997 ▶); Liu et al. (1980 ▶); Zhou et al. (1999 ▶). For a related structure, see: Wang et al. (2003 ▶).

Experimental

Crystal data

C₂₀H₁₉N₃O
M _r = 317.38
Orthorhombic,
a = 8.9790 (18) Å
b = 18.500 (4) Å
c = 20.050 (4) Å
V = 3330.5 (12) Å³
Z = 8
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 113 K
0.24 × 0.21 × 0.20 mm

Data collection

Rigaku Saturn70 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.863, T _max = 0.884
34928 measured reflections
3262 independent reflections
2946 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.104
S = 1.06
3262 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2005 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013723/ci5077sup1.cif

e-66-o1123-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013723/ci5077Isup2.hkl

e-66-o1123-Isup2.hkl^{(160.1KB, 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
N3—H1⋯O1	0.92 (2)	1.88 (2)	2.6726 (15)	143 (2)
C20—H20⋯O1	0.95	2.36	2.9453 (16)	120
C10—H10⋯O1ⁱ	0.95	2.30	3.1809 (17)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant No. 20772066).

supplementary crystallographic information

Comment

1-Phenyl-3-methyl-4-benzoylpyrazolon-5-one (HPMBP), an effective β-diketonate, is widely used and well known for its extractive ability. In recent years, HPMBP and its metal complexes have also been found to have good antibacterial and biological properties. Its metal complexes have analgesic activity (Liu et al., 1980; Li et al., 1997; Zhou et al., 1999). In order to develop new medicines, we have synthesized the title compound and its crystal structure is reported here.

The structure of the title molecule is shown in Fig. 1. The dihedral angles formed by the pyrazolone ring with the C6–C11 and C15–C20 phenyl rings and cyclopropane ring are 64.27 (6)°, 17.00 (6)° and 71.28 (11)°, respectively. The O atom of the 3-methyl-1-phenylpyrazol-5-one moiety and the N atom of the amino group are available for coordination with metals. Atoms O1, C1, C2, C5 and N3 are coplanar (r.m.s. deviation = 0.028 Å). The dihedral angle between this plane and the pyrazoline ring is 4.34 (7)°, close to the value of 3.56 (3)° found in 4-{[3,4-dihydro-5-methyl-3-oxo-2-phenyl-2H-pyrazol-4-ylidene(phenyl) methylamino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Wang et al., 2003). The bond lengths within this part of the molecule lie between classical single- and double-bond lengths, indicating extensive conjugation. A strong intramolecular N3—H1···O1 hydrogen bond (Table 1) is observed, leading to a keto-enamine form. The molecule is further stabilized by a C—H···O weak intramolecular hydrogen bond (Table 1).

The crystal structure also involves weak intermolecular C—H···O hydrogen-bond interactions (Fig. 2).

Experimental

The title compound was synthesized by refluxing a mixture of 1-phenyl-3- methyl-4-benzoylpyrazol-5-one (10 mmol) and cyclopropanamine (10 mmol) in ethanol (80 ml) over a steam bath for about 16 h. Excess solvent was removed by evaporation and the solution was cooled to room temperature. After 2 d, a colourless solid was obtained and this was dried in air. The product was recrystallized from ethanol, to afford colourless crystals of the title compound suitable for X-ray analysis.