5-(3-Fluoro­phen­yl)-1-phenyl­pyrazolidin-3-one

Yuan-Yuan Liu; Hong Shi; Qing-Yan Chu; Hong-Jun Zhu

doi:10.1107/S1600536808026706

. 2008 Sep 6;64(Pt 10):o1886. doi: 10.1107/S1600536808026706

5-(3-Fluorophenyl)-1-phenylpyrazolidin-3-one

Yuan-Yuan Liu ^a, Hong Shi ^a, Qing-Yan Chu ^a, Hong-Jun Zhu ^a,^*

PMCID: PMC2959324 PMID: 21201098

Abstract

In the molecule of the title compound, C₁₅H₁₃FN₂O, the phenyl and fluorophenyl rings are oriented at a dihedral angle of 77.92 (3)°. The pyrazolidine ring adopts an envelope conformation. An intramolecular C—H⋯N hydrogen bond results in the formation of a five-membered ring adopting an envelope conformation. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules. There are C—H⋯π contacts between between aromatic H atoms and the phenyl and fluorophenyl rings. A π–π contact between phenyl rings [centroid–centroid distance = 3.926 (1) Å] is also observed.

Related literature

For general background, see: Chiara & Garcia (2005 ▶). For related literature, see: Jia et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₃FN₂O
M _r = 256.27
Monoclinic,
a = 10.265 (2) Å
b = 7.3130 (15) Å
c = 17.822 (4) Å
β = 92.39 (3)°
V = 1336.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.973, T _max = 0.991
2393 measured reflections
2393 independent reflections
1231 reflections with I > 2σ(I)
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.232
S = 1.07
2393 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablocks I, lyy. DOI: 10.1107/S1600536808026706/hk2512sup1.cif

e-64-o1886-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026706/hk2512Isup2.hkl

e-64-o1886-Isup2.hkl^{(117.6KB, 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
N2—H2A⋯Oⁱ	0.86	1.92	2.777 (4)	172
C4—H4A⋯N1	0.93	2.48	2.836 (6)	103
C8—H8A⋯Oⁱⁱ	0.97	2.59	3.422 (5)	143
C6—H6A⋯Cg3ⁱⁱⁱ	0.93	2.96	3.866 (3)	165
C12—H12A⋯Cg2^iv	0.93	3.05	3.751 (3)	134
C14—H14A⋯Cg3^v	0.93	2.80	3.654 (3)	153

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) . Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

Pyrazolidin-3-one and its derivatives used as medicines and herbicides (Chiara & Garcia, 2005) have been developed most quickly, such as anodyne and antipyretic. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and C (C10-C15) are, of course, planar, and they are oriented at a dihedral angle of A/C = 77.92 (3)°. Ring B (N1/N2/C7-C9) adopts envelope conformation, with C8 atom displaced by 0.277 (3) Å from the plane of the other ring atoms. The intra- molecular C-H···N hydrogen bond (Table 1) results in the formation of a five-membered ring D (N1/C4/C5/C7/H4A) adopting envelope conformation, with N1 atom displaced by -0.326 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular N-H···O and C-H···O hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. The C—H···π contacts (Table 1) between the phenyl rings and the aromatic H atoms and a π—π contact between phenyl rings Cg2···Cg2ⁱ [symmetry code: (i) -x, 1 - y, 1 - z, where Cg2 is centroid of the ring A (C1-C6)] further stabilize the structure, with centroid-centroid distance of 3.926 (1) Å.

Experimental

The title compound was prepared according to the literature method (Jia et al., 2008). The crystals were obtained by dissolving the title compound (1.5 g) in ethyl acetate (25 ml) and evaporating the solvent slowly at room temperature for about 10 d.