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

Liu, Y.-Y.; Shi, H.; Chu, Q.-Y.; Zhu, H.-J.

doi:10.1107/S1600536808026706

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1886

doi:10.1107/S1600536808026706

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

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

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 13 August 2008; accepted 19 August 2008; online 6 September 2008)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.081
wR(F²) = 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

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
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) -x+1, -y, -z+1; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.

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.

Supporting information

Crystal structure: contains datablocks I, lyy. DOI: 10.1107/S1600536808026706/hk2512sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

For general background, see: Chiara & Garcia (2005). For related literature, see: Jia et al. (2008). For bond-length data, see: Allen et al. (1987). Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.

Experimental top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

5-(3-fluorophenyl)-1-phenylpyrazolidin-3-one top

Crystal data top

C₁₅H₁₃FN₂O	F(000) = 536
M_r = 256.27	D_x = 1.273 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.265 (2) Å	θ = 9–12°
b = 7.3130 (15) Å	µ = 0.09 mm⁻¹
c = 17.822 (4) Å	T = 294 K
β = 92.39 (3)°	Needle, colorless
V = 1336.7 (5) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1231 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.2°, θ_min = 2.0°
ω/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
T_min = 0.973, T_max = 0.991	l = 0→21
2393 measured reflections	3 standard reflections every 120 min
2393 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.081	H-atom parameters constrained
wR(F²) = 0.232	w = 1/[σ²(F_o²) + (0.1065P)² + 0.1962P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2393 reflections	Δρ_max = 0.34 e Å⁻³
166 parameters	Δρ_min = −0.75 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₃FN₂O	V = 1336.7 (5) Å³
M_r = 256.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.265 (2) Å	µ = 0.09 mm⁻¹
b = 7.3130 (15) Å	T = 294 K
c = 17.822 (4) Å	0.30 × 0.20 × 0.10 mm
β = 92.39 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1231 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.973, T_max = 0.991	3 standard reflections every 120 min
2393 measured reflections	intensity decay: none
2393 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	166 parameters
wR(F²) = 0.232	H-atom parameters constrained
S = 1.07	Δρ_max = 0.34 e Å⁻³
2393 reflections	Δρ_min = −0.75 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O	0.0023 (3)	0.2565 (4)	0.22989 (17)	0.0567 (8)
F	0.2688 (3)	0.7468 (5)	0.56248 (19)	0.098
N1	0.2364 (3)	0.0858 (4)	0.35618 (19)	0.0407 (8)
C1	0.2186 (8)	0.5785 (10)	0.5378 (4)	0.104 (2)
N2	0.1332 (3)	0.0777 (4)	0.3021 (2)	0.0477 (9)
H2A	0.0965	−0.0235	0.2886	0.057*
C2	0.1419 (7)	0.4819 (12)	0.5800 (4)	0.095 (2)
H2B	0.1174	0.5252	0.6264	0.114*
C3	0.0997 (6)	0.3176 (11)	0.5537 (3)	0.0873 (18)
H3A	0.0426	0.2492	0.5816	0.105*
C4	0.1399 (5)	0.2505 (7)	0.4868 (3)	0.0650 (13)
H4A	0.1112	0.1361	0.4704	0.078*
C5	0.2215 (4)	0.3492 (6)	0.4436 (2)	0.0488 (11)
C6	0.2666 (6)	0.5199 (7)	0.4691 (3)	0.0790 (16)
H6A	0.3245	0.5898	0.4424	0.095*
C7	0.2639 (4)	0.2853 (5)	0.3683 (2)	0.0421 (10)
H7A	0.3576	0.3073	0.3647	0.051*
C8	0.1895 (4)	0.3791 (5)	0.3012 (2)	0.0452 (10)
H8A	0.1435	0.4870	0.3174	0.054*
H8B	0.2487	0.4137	0.2626	0.054*
C9	0.0967 (4)	0.2358 (5)	0.2735 (2)	0.0433 (10)
C10	0.3413 (3)	−0.0333 (5)	0.3443 (2)	0.0385 (9)
C11	0.4505 (4)	−0.0252 (6)	0.3943 (2)	0.0509 (11)
H11A	0.4529	0.0611	0.4327	0.061*
C12	0.5555 (4)	−0.1441 (7)	0.3875 (3)	0.0592 (13)
H12A	0.6282	−0.1359	0.4203	0.071*
C13	0.5499 (5)	−0.2750 (6)	0.3310 (3)	0.0660 (14)
H13A	0.6185	−0.3569	0.3265	0.079*
C14	0.4453 (4)	−0.2840 (6)	0.2825 (3)	0.0573 (12)
H14A	0.4430	−0.3718	0.2447	0.069*
C15	0.3405 (4)	−0.1633 (5)	0.2880 (2)	0.0423 (10)
H15A	0.2699	−0.1706	0.2537	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0586 (18)	0.0318 (16)	0.079 (2)	0.0078 (14)	−0.0066 (17)	0.0028 (15)
F	0.098	0.098	0.098	0.000	0.004	0.000
N1	0.0375 (18)	0.0253 (17)	0.059 (2)	0.0030 (14)	−0.0036 (16)	−0.0029 (15)
C1	0.125 (6)	0.083 (5)	0.101 (5)	0.018 (4)	−0.022 (5)	−0.058 (4)
N2	0.0402 (19)	0.0242 (17)	0.078 (3)	0.0014 (15)	−0.0117 (18)	0.0065 (16)
C2	0.089 (5)	0.132 (7)	0.063 (4)	0.044 (5)	0.007 (3)	−0.022 (4)
C3	0.081 (4)	0.117 (6)	0.064 (4)	0.015 (4)	0.002 (3)	0.008 (4)
C4	0.055 (3)	0.067 (3)	0.072 (3)	0.008 (3)	−0.002 (3)	0.000 (3)
C5	0.043 (2)	0.045 (3)	0.058 (3)	0.010 (2)	−0.004 (2)	−0.005 (2)
C6	0.109 (4)	0.063 (3)	0.065 (3)	−0.010 (3)	0.006 (3)	−0.027 (3)
C7	0.040 (2)	0.0212 (19)	0.066 (3)	−0.0020 (17)	0.0037 (19)	−0.0048 (19)
C8	0.040 (2)	0.030 (2)	0.066 (3)	−0.0010 (18)	0.007 (2)	−0.003 (2)
C9	0.042 (2)	0.031 (2)	0.057 (2)	0.0024 (19)	0.005 (2)	−0.013 (2)
C10	0.032 (2)	0.031 (2)	0.052 (2)	0.0004 (17)	−0.0015 (18)	0.0085 (19)
C11	0.047 (2)	0.049 (3)	0.056 (3)	0.014 (2)	−0.004 (2)	−0.009 (2)
C12	0.051 (3)	0.063 (3)	0.062 (3)	0.006 (2)	−0.017 (2)	0.009 (3)
C13	0.052 (3)	0.043 (3)	0.105 (4)	0.012 (2)	0.023 (3)	0.001 (3)
C14	0.055 (3)	0.042 (3)	0.076 (3)	0.006 (2)	0.024 (2)	−0.017 (2)
C15	0.038 (2)	0.039 (2)	0.050 (2)	−0.0045 (19)	0.0006 (18)	−0.0047 (19)

Geometric parameters (Å, º) top

O—C9	1.226 (5)	C6—H6A	0.9300
F—C1	1.398 (7)	C7—C8	1.552 (6)
N1—N2	1.404 (4)	C7—H7A	0.9800
N1—C10	1.408 (5)	C8—C9	1.487 (5)
N1—C7	1.500 (4)	C8—H8A	0.9700
C1—C2	1.317 (9)	C8—H8B	0.9700
C1—C6	1.405 (9)	C10—C15	1.381 (5)
N2—C9	1.311 (5)	C10—C11	1.404 (5)
N2—H2A	0.8600	C11—C12	1.394 (6)
C2—C3	1.354 (9)	C11—H11A	0.9300
C2—H2B	0.9300	C12—C13	1.389 (6)
C3—C4	1.370 (8)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.353 (6)
C4—C5	1.366 (7)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.398 (6)
C5—C6	1.400 (6)	C14—H14A	0.9300
C5—C7	1.502 (6)	C15—H15A	0.9300

N2—N1—C10	115.5 (3)	C8—C7—H7A	109.2
N2—N1—C7	105.8 (3)	C9—C8—C7	103.4 (3)
C10—N1—C7	118.9 (3)	C9—C8—H8A	111.1
C2—C1—F	120.9 (7)	C7—C8—H8A	111.1
C2—C1—C6	125.0 (6)	C9—C8—H8B	111.1
F—C1—C6	113.9 (7)	C7—C8—H8B	111.1
C9—N2—N1	115.1 (3)	H8A—C8—H8B	109.0
C9—N2—H2A	122.4	O—C9—N2	124.1 (4)
N1—N2—H2A	122.4	O—C9—C8	127.0 (4)
C1—C2—C3	117.9 (6)	N2—C9—C8	108.9 (3)
C1—C2—H2B	121.0	C15—C10—C11	118.0 (4)
C3—C2—H2B	121.0	C15—C10—N1	123.6 (3)
C2—C3—C4	121.1 (6)	C11—C10—N1	118.3 (3)
C2—C3—H3A	119.5	C12—C11—C10	121.2 (4)
C4—C3—H3A	119.5	C12—C11—H11A	119.4
C5—C4—C3	121.0 (5)	C10—C11—H11A	119.4
C5—C4—H4A	119.5	C13—C12—C11	119.0 (4)
C3—C4—H4A	119.5	C13—C12—H12A	120.5
C4—C5—C6	119.4 (4)	C11—C12—H12A	120.5
C4—C5—C7	123.0 (4)	C14—C13—C12	120.3 (4)
C6—C5—C7	117.6 (4)	C14—C13—H13A	119.8
C5—C6—C1	115.6 (6)	C12—C13—H13A	119.8
C5—C6—H6A	122.2	C13—C14—C15	121.1 (4)
C1—C6—H6A	122.2	C13—C14—H14A	119.4
N1—C7—C5	111.8 (3)	C15—C14—H14A	119.4
N1—C7—C8	103.6 (3)	C10—C15—C14	120.3 (4)
C5—C7—C8	113.6 (3)	C10—C15—H15A	119.8
N1—C7—H7A	109.2	C14—C15—H15A	119.8
C5—C7—H7A	109.2

C10—N1—N2—C9	−128.7 (4)	C6—C5—C7—C8	−76.9 (5)
C7—N1—N2—C9	5.0 (5)	N1—C7—C8—C9	17.4 (4)
F—C1—C2—C3	−178.1 (5)	C5—C7—C8—C9	−104.2 (4)
C6—C1—C2—C3	−3.9 (11)	N1—N2—C9—O	−174.3 (4)
C1—C2—C3—C4	2.6 (9)	N1—N2—C9—C8	7.0 (5)
C2—C3—C4—C5	−1.4 (8)	C7—C8—C9—O	166.0 (4)
C3—C4—C5—C6	1.2 (7)	C7—C8—C9—N2	−15.3 (4)
C3—C4—C5—C7	−177.3 (4)	N2—N1—C10—C15	−6.1 (5)
C4—C5—C6—C1	−2.1 (7)	C7—N1—C10—C15	−133.5 (4)
C7—C5—C6—C1	176.5 (5)	N2—N1—C10—C11	176.8 (3)
C2—C1—C6—C5	3.6 (10)	C7—N1—C10—C11	49.4 (5)
F—C1—C6—C5	178.2 (5)	C15—C10—C11—C12	0.2 (6)
N2—N1—C7—C5	108.7 (3)	N1—C10—C11—C12	177.4 (4)
C10—N1—C7—C5	−119.4 (4)	C10—C11—C12—C13	−1.3 (7)
N2—N1—C7—C8	−13.9 (4)	C11—C12—C13—C14	1.4 (7)
C10—N1—C7—C8	117.9 (4)	C12—C13—C14—C15	−0.4 (7)
C4—C5—C7—N1	−15.1 (5)	C11—C10—C15—C14	0.8 (6)
C6—C5—C7—N1	166.3 (4)	N1—C10—C15—C14	−176.2 (4)
C4—C5—C7—C8	101.7 (4)	C13—C14—C15—C10	−0.8 (7)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+1, −y, −z+1; (v) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃FN₂O
M_r	256.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	10.265 (2), 7.3130 (15), 17.822 (4)
β (°)	92.39 (3)
V (Å³)	1336.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	2393, 2393, 1231
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.232, 1.07
No. of reflections	2393
No. of parameters	166
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.75

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Oⁱ	0.86	1.92	2.777 (4)	172.00
C4—H4A···N1	0.93	2.48	2.836 (6)	103.00
C8—H8A···Oⁱⁱ	0.97	2.59	3.422 (5)	143.00
C6—H6A···Cg3ⁱⁱⁱ	0.93	2.96	3.866 (3)	165.00
C12—H12A···Cg2^iv	0.93	3.05	3.751 (3)	134.00
C14—H14A···Cg3^v	0.93	2.80	3.654 (3)	153.00

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+1, −y, −z+1; (v) −x+1, y−1/2, −z+1/2.

Acknowledgements

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

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