5-(3-Fluoro-phen-yl)-1-phenyl-pyrazolidin-3-one.

In the mol-ecule of the title compound, C(15)H(13)FN(2)O, the phenyl and fluorophenyl rings are oriented at a dihedral angle of 77.92 (3)°. The pyrazolidine ring adopts an envelope conformation. An intra-molecular C-H⋯N hydrogen bond results in the formation of a five-membered ring adopting an envelope conformation. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules. 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 = 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

Δρmax = 0.34 e Å−3

Δρmin = −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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H13FN2O	F(000) = 536
Mr = 256.27	Dx = 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

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

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(Fo2) + (0.1065P)2 + 0.1962P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2393 reflections	Δρmax = 0.34 e Å−3
166 parameters	Δρmin = −0.75 e Å−3
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg2iv	0.93	3.05	3.751 (3)	134.
C14—H14A···Cg3v	0.93	2.80	3.654 (3)	153.

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⋯Cg2iv	0.93	3.05	3.751 (3)	134
C14—H14A⋯Cg3v	0.93	2.80	3.654 (3)	153

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