Methyl 2-{[(2-fur­yl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)meth­yl]amino}­acetate

Xiao Han; Xiao-Dong Yang; Xiao-Chang Dai

doi:10.1107/S1600536811026158

. 2011 Jul 6;67(Pt 8):o1936. doi: 10.1107/S1600536811026158

Methyl 2-{[(2-furyl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)methyl]amino}acetate

Xiao Han ^a,^*, Xiao-Dong Yang ^a, Xiao-Chang Dai ^a

PMCID: PMC3212323 PMID: 22090980

Abstract

In the title compound, C₁₈H₁₇N₃O₄, the amino group of the glycine methyl ester fragment is involved in an intramolecular N—H⋯O hydrogen bond. The phenyl and furyl rings form dihedral angles of 10.20 (4) and 54.56°, respectively, with the pyrazole ring. In the crystal, molecules related by translation along the b axis are linked into chains via weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Zhang et al. (2007 ▶). For details of the synthesis, see: Jensen (1959 ▶). For applications of pyrazolone derivatives in coordination chemistry, see: Casas et al. (2007 ▶). For the antibacterial activity of pyrazolone derivatives, see: Li et al. (2000 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C₁₈H₁₇N₃O₄
M _r = 339.35
Triclinic,
a = 7.499 (4) Å
b = 9.503 (5) Å
c = 11.749 (6) Å
α = 96.712 (7)°
β = 91.654 (8)°
γ = 90.337 (7)°
V = 831.2 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.48 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
6492 measured reflections
2915 independent reflections
1805 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.150
S = 1.01
29015 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026158/cv5123sup1.cif

e-67-o1936-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026158/cv5123Isup2.hkl

e-67-o1936-Isup2.hkl^{(142.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026158/cv5123Isup3.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	0.97 (3)	1.89 (3)	2.704 (3)	140 (2)
C14—H14⋯O1ⁱ	0.93	2.48	3.386 (4)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support from the study on structure–activity relationships of helicid analogues.

supplementary crystallographic information

Comment

Pyrazolones constitute an important class of heterocycles due to their properties and applications (Casas et al., 2007). Schiff bases derived from 1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone (PMFP) have found extensive application in coordination chemistry and due to their antibacterial activity (Zhang et al., 2007, 2008; Li et al., 2000). In order to expand this field, we present here the title compound (I).

In (I) (Fig. 1), the phenyl ring (C1-C6) is twisted at 10.20 (4)° from the mean plane of pyrazole ring. The pyrazole ring and the O1/C10/C9/C11/N3 mean form a dihedral angle of 5.62 (4)°. The bond length of C9—C11(1.390 (3) Å) between the usual C—C and C=C bonds indicates the delocalization of the electrons. Strong intramolecular hydrogen bond N3—H3A···O1(Table 1) is indicative of the enamine-keto form.

In the crystal structure, molecules related by translation along axis b are linked into chains via weak intermolecular C—H···O hydrogen bonds.

Experimental

PMFP was synthesized according to the method proposed by Jensen (1959). A mixture of a 10 ml PMFP (2 mmol, 0.5366 g) anhydrous ethanol solution, and 10 ml Glycine methyl ester hydrochloride anhydrous ethanol solution (2 mmol, 0.2511 g)solution was refluxed for ca.7 h, adding a few drops of glacial acetic acid as a catalyst. Then ethanol was removed by evaporation and the resulting black precipitate formed was filtered off, washed with cold anhydrous ethanol and dried in air. Black block single crystals suitable for analysis were obtained by slowly evaporation of a solution in anhydrous ethanol at room temperature for a few days.