1-(4-Fluoro­phen­yl)-5-(4-methoxy­phen­yl)pyrazolidin-3-one

Bao-Jiang Dai; Yuan-Yuan Liu; Qing-Bing Xu; Jing Hu; Hong-Jun Zhu

doi:10.1107/S1600536809007144

. 2009 Mar 6;65(Pt 4):o675. doi: 10.1107/S1600536809007144

1-(4-Fluorophenyl)-5-(4-methoxyphenyl)pyrazolidin-3-one

Bao-Jiang Dai ^a, Yuan-Yuan Liu ^b, Qing-Bing Xu ^b, Jing Hu ^b, Hong-Jun Zhu ^b,^*

PMCID: PMC2968975 PMID: 21582419

Abstract

In the molecule of the title compound, C₁₆H₁₅FN₂O₂, the benzene rings are oriented at a dihedral angle of 88.61 (3)°. The five-membered ring adopts an envelope conformation. Intramolecular C—H⋯N hydrogen bonds result in the formation of two planar five-membered rings. In the crystal structure, intermolecular N—H⋯O and C—H⋯F hydrogen bonds link the molecules, forming R ₂ ²(8) and R ₂ ²(18) ring motifs. Weak C—H⋯π interactions may further stabilize the structure.

Related literature

For applications of pyrazolidin-3-one, see: Prakash et al. (2008 ▶); Nonaka (2003 ▶); Mabuchi & Ohtsuka (1999 ▶). For a related structure, see: Liu et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₅FN₂O₂
M _r = 286.30
Monoclinic,
a = 11.455 (2) Å
b = 7.1590 (14) Å
c = 18.136 (4) Å
β = 101.05 (3)°
V = 1459.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.4 × 0.4 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.969, T _max = 0.991
2991 measured reflections
2844 independent reflections
1869 reflections with I > 2σ(I)
R _int = 0.023
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.164
S = 1.01
2844 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007144/hk2631sup1.cif

e-65-0o675-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007144/hk2631Isup2.hkl

e-65-0o675-Isup2.hkl^{(139.6KB, 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⋯O1ⁱ	0.86	1.98	2.838 (2)	175
C5—H5A⋯N2	0.93	2.43	2.747 (3)	100
C8—H8A⋯Fⁱⁱ	0.97	2.45	3.388 (3)	164
C11—H11A⋯N1	0.93	2.53	2.885 (3)	103
C2—H2B⋯Cg2ⁱⁱⁱ	0.93	2.71	3.589 (3)	157
C15—H15A⋯Cg1^iv	0.93	2.89	3.801 (3)	167

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are centroids of the C1–C6 andC10–C15 rings, respectively.

Acknowledgments

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

supplementary crystallographic information

Comment

Nowadays, pyrazolidin-3-one and its derivatives used as pesticide have been developed most quickly, such as antiseptic (Prakash et al., 2008), insecticide (Nonaka, 2003) and herbicide (Mabuchi & Ohtsuka, 1999). 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 88.61 (3)°. The five-membered ring B (N1/N2/C7-C9) adopts envelope conformation with C7 atom displaced by 0.363 (3) Å from the plane of the other ring atoms. The intramolecular C-H···N hydrogen bonds (Table 1) results in the formations of two planar five-membered rings D (N1/N2/C4/C5/H5A) and E (N1/C7/C10/C11/H11A), in which they are oriented with respect to the adjacent rings at dihedral angles of A/D = 4.87 (3) and C/E = 0.86 (3)°. So, rings C and E are coplanar, while A and D are nearly coplanar.

In the crystal structure, intermolecular N-H···O and C-H···F hydrogen bonds (Table 2) link the molecules (Fig. 2) by forming the R₂²(8) and R₂²(18) ring motifs (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The weak C—H···π interactions (Table 1) may further stabilize the structure.

Experimental

The title compound was prepared according to the literature method (Liu et al., 2008). Crystals suitable for X-ray analysis 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.