1-(4-Fluoro-phen-yl)-5-(4-methoxy-phen-yl)pyrazolidin-3-one.

In the mol-ecule of the title compound, C(16)H(15)FN(2)O(2), the benzene rings are oriented at a dihedral angle of 88.61 (3)°. The five-membered ring adopts an envelope conformation. Intra-molecular C-H⋯N hydrogen bonds result in the formation of two planar five-membered rings. In the crystal structure, inter-molecular N-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules, forming R(2) (2)(8) and R(2) (2)(18) ring motifs. Weak C-H⋯π inter-actions 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 = 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

Δρmax = 0.18 e Å−3

Δρmin = −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 ▶).

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

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

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

C16H15FN2O2	F(000) = 600
Mr = 286.30	Dx = 1.303 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.455 (2) Å	θ = 10–13°
b = 7.1590 (14) Å	µ = 0.10 mm−1
c = 18.136 (4) Å	T = 294 K
β = 101.05 (3)°	Needle, colorless
V = 1459.7 (5) Å3	0.4 × 0.4 × 0.3 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 26.0°, θmin = 1.8°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.969, Tmax = 0.991	l = −21→21
2991 measured reflections	3 standard reflections every 120 min
2844 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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2844 reflections	Δρmax = 0.18 e Å−3
191 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (5)

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 > σ(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
O1	0.48784 (13)	0.2552 (2)	0.03274 (8)	0.0523 (4)
O2	0.38835 (15)	−0.1685 (2)	−0.36578 (8)	0.0597 (5)
N1	0.26509 (14)	0.3997 (2)	−0.11625 (9)	0.0405 (4)
N2	0.37005 (14)	0.4183 (2)	−0.06107 (10)	0.0468 (5)
H2A	0.4116	0.5192	−0.0556	0.056*
F	−0.11183 (16)	0.8402 (3)	−0.07221 (14)	0.1260 (8)
C1	−0.0185 (2)	0.7276 (4)	−0.08105 (18)	0.0724 (8)
C2	−0.0298 (2)	0.6229 (4)	−0.14437 (16)	0.0694 (8)
H2B	−0.0996	0.6247	−0.1803	0.083*
C3	0.0654 (2)	0.5135 (3)	−0.15406 (13)	0.0541 (6)
H3A	0.0603	0.4424	−0.1975	0.065*
C4	0.16815 (17)	0.5086 (2)	−0.09998 (11)	0.0393 (5)
C5	0.1755 (2)	0.6150 (3)	−0.03597 (12)	0.0525 (6)
H5A	0.2443	0.6122	0.0009	0.063*
C6	0.0806 (2)	0.7261 (4)	−0.02653 (17)	0.0723 (8)
H6A	0.0848	0.7985	0.0165	0.087*
C7	0.24222 (18)	0.1930 (3)	−0.12010 (11)	0.0393 (5)
H7A	0.1569	0.1709	−0.1237	0.047*
C8	0.30920 (19)	0.1193 (3)	−0.04418 (10)	0.0436 (5)
H8A	0.2559	0.1040	−0.0090	0.052*
H8B	0.3472	0.0006	−0.0501	0.052*
C9	0.39987 (18)	0.2682 (3)	−0.01826 (11)	0.0416 (5)
C10	0.28206 (17)	0.1019 (3)	−0.18638 (10)	0.0391 (5)
C11	0.33591 (18)	0.1959 (3)	−0.23771 (11)	0.0443 (5)
H11A	0.3490	0.3238	−0.2323	0.053*
C12	0.3703 (2)	0.1032 (3)	−0.29659 (11)	0.0486 (5)
H12A	0.4069	0.1687	−0.3302	0.058*
C13	0.35087 (19)	−0.0874 (3)	−0.30603 (10)	0.0455 (5)
C14	0.2963 (2)	−0.1830 (3)	−0.25569 (13)	0.0592 (7)
H14A	0.2825	−0.3107	−0.2613	0.071*
C15	0.2625 (2)	−0.0876 (3)	−0.19703 (12)	0.0560 (6)
H15A	0.2254	−0.1529	−0.1636	0.067*
C16	0.3801 (2)	−0.3669 (4)	−0.37188 (14)	0.0655 (7)
H16A	0.4084	−0.4069	−0.4158	0.098*
H16B	0.2987	−0.4044	−0.3758	0.098*
H16C	0.4276	−0.4230	−0.3281	0.098*

	U11	U22	U33	U12	U13	U23
O1	0.0529 (9)	0.0421 (9)	0.0565 (9)	0.0060 (7)	−0.0034 (7)	0.0017 (7)
O2	0.0751 (11)	0.0584 (11)	0.0486 (9)	−0.0018 (8)	0.0194 (8)	−0.0099 (7)
N1	0.0387 (9)	0.0295 (9)	0.0521 (10)	0.0020 (7)	0.0053 (7)	−0.0001 (7)
N2	0.0361 (9)	0.0319 (9)	0.0678 (11)	−0.0014 (7)	−0.0017 (8)	0.0030 (8)
F	0.0732 (12)	0.1078 (16)	0.200 (2)	0.0392 (11)	0.0325 (13)	−0.0413 (15)
C1	0.0470 (14)	0.0575 (16)	0.114 (2)	0.0138 (12)	0.0199 (15)	−0.0134 (15)
C2	0.0464 (14)	0.0637 (17)	0.0911 (19)	0.0095 (12)	−0.0040 (13)	−0.0011 (15)
C3	0.0482 (13)	0.0478 (13)	0.0622 (14)	0.0055 (10)	−0.0001 (10)	−0.0054 (11)
C4	0.0425 (11)	0.0267 (10)	0.0486 (11)	0.0025 (8)	0.0082 (9)	0.0043 (8)
C5	0.0536 (13)	0.0472 (13)	0.0551 (13)	0.0021 (10)	0.0069 (10)	−0.0084 (10)
C6	0.0711 (18)	0.0606 (17)	0.0880 (19)	0.0055 (13)	0.0226 (15)	−0.0289 (14)
C7	0.0399 (10)	0.0281 (10)	0.0501 (11)	−0.0005 (8)	0.0090 (9)	0.0009 (8)
C8	0.0552 (13)	0.0344 (11)	0.0425 (11)	−0.0020 (9)	0.0131 (9)	0.0010 (9)
C9	0.0455 (11)	0.0328 (11)	0.0476 (11)	0.0064 (9)	0.0122 (9)	−0.0014 (9)
C10	0.0441 (11)	0.0322 (10)	0.0395 (10)	0.0001 (8)	0.0044 (8)	0.0022 (8)
C11	0.0478 (12)	0.0341 (10)	0.0495 (12)	−0.0044 (9)	0.0060 (9)	0.0027 (9)
C12	0.0550 (13)	0.0484 (13)	0.0434 (11)	−0.0081 (10)	0.0120 (10)	0.0032 (9)
C13	0.0501 (12)	0.0479 (13)	0.0365 (10)	0.0015 (10)	0.0032 (9)	−0.0026 (9)
C14	0.0896 (19)	0.0362 (12)	0.0557 (13)	−0.0053 (12)	0.0238 (13)	−0.0048 (10)
C15	0.0857 (17)	0.0367 (12)	0.0518 (12)	−0.0080 (11)	0.0287 (12)	0.0011 (9)
C16	0.0717 (16)	0.0648 (16)	0.0614 (14)	−0.0109 (13)	0.0162 (12)	−0.0278 (13)

O1—C9	1.234 (2)	C7—C8	1.536 (3)
O2—C13	1.369 (2)	C7—C10	1.513 (3)
O2—C16	1.427 (3)	C7—H7A	0.9800
N1—N2	1.415 (2)	C8—H8A	0.9700
N1—C4	1.433 (2)	C8—H8B	0.9700
N1—C7	1.502 (2)	C9—C8	1.500 (3)
N2—C9	1.331 (2)	C10—C15	1.382 (3)
N2—H2A	0.8600	C11—C10	1.386 (3)
F—C1	1.372 (3)	C11—C12	1.378 (3)
C2—C1	1.357 (4)	C11—H11A	0.9300
C2—H2B	0.9300	C12—C13	1.388 (3)
C3—C2	1.380 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.382 (3)
C4—C3	1.381 (3)	C14—C15	1.381 (3)
C4—C5	1.378 (3)	C14—H14A	0.9300
C5—C6	1.384 (3)	C15—H15A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C6—C1	1.356 (4)	C16—H16B	0.9600
C6—H6A	0.9300	C16—H16C	0.9600
C13—O2—C16	117.22 (18)	C7—C8—H8B	111.1
N2—N1—C4	112.97 (15)	C9—C8—C7	103.53 (16)
N2—N1—C7	104.02 (14)	C9—C8—H8A	111.1
C4—N1—C7	114.23 (15)	C9—C8—H8B	111.1
N1—N2—H2A	122.4	H8A—C8—H8B	109.0
C9—N2—N1	115.13 (16)	O1—C9—N2	125.42 (19)
C9—N2—H2A	122.4	O1—C9—C8	126.75 (18)
C2—C1—F	118.3 (3)	N2—C9—C8	107.82 (17)
C6—C1—F	118.8 (3)	C15—C10—C11	117.64 (19)
C6—C1—C2	122.9 (2)	C15—C10—C7	117.95 (18)
C1—C2—C3	118.2 (2)	C11—C10—C7	124.40 (18)
C1—C2—H2B	120.9	C10—C11—H11A	119.4
C3—C2—H2B	120.9	C12—C11—C10	121.1 (2)
C2—C3—C4	120.7 (2)	C12—C11—H11A	119.4
C2—C3—H3A	119.7	C11—C12—C13	120.42 (19)
C4—C3—H3A	119.7	C11—C12—H12A	119.8
C3—C4—N1	117.15 (18)	C13—C12—H12A	119.8
C5—C4—N1	123.33 (18)	O2—C13—C14	124.3 (2)
C5—C4—C3	119.40 (19)	O2—C13—C12	116.56 (19)
C4—C5—C6	120.0 (2)	C14—C13—C12	119.17 (19)
C4—C5—H5A	120.0	C15—C14—C13	119.6 (2)
C6—C5—H5A	120.0	C15—C14—H14A	120.2
C1—C6—C5	118.9 (2)	C13—C14—H14A	120.2
C1—C6—H6A	120.6	C10—C15—H15A	119.0
C5—C6—H6A	120.6	C14—C15—C10	122.1 (2)
N1—C7—C8	104.13 (15)	C14—C15—H15A	119.0
N1—C7—C10	112.66 (16)	O2—C16—H16A	109.5
N1—C7—H7A	109.0	O2—C16—H16B	109.5
C8—C7—H7A	109.0	O2—C16—H16C	109.5
C10—C7—C8	112.90 (16)	H16A—C16—H16B	109.5
C10—C7—H7A	109.0	H16A—C16—H16C	109.5
C7—C8—H8A	111.1	H16B—C16—H16C	109.5
C4—N1—N2—C9	109.31 (19)	C4—C5—C6—C1	0.1 (4)
C7—N1—N2—C9	−15.1 (2)	C5—C6—C1—C2	0.8 (5)
N2—N1—C4—C3	174.02 (17)	C5—C6—C1—F	−178.9 (3)
N2—N1—C4—C5	−2.1 (3)	N1—C7—C8—C9	−21.70 (19)
C7—N1—C4—C3	−67.3 (2)	C10—C7—C8—C9	100.83 (19)
C7—N1—C4—C5	116.5 (2)	N1—C7—C10—C11	1.1 (3)
N2—N1—C7—C8	22.13 (18)	N1—C7—C10—C15	−178.22 (19)
N2—N1—C7—C10	−100.56 (17)	C8—C7—C10—C11	−116.5 (2)
C4—N1—C7—C8	−101.47 (18)	C8—C7—C10—C15	64.2 (2)
C4—N1—C7—C10	135.84 (17)	O1—C9—C8—C7	−165.5 (2)
N1—N2—C9—O1	179.81 (18)	N2—C9—C8—C7	13.5 (2)
N1—N2—C9—C8	0.8 (2)	C7—C10—C15—C14	−179.7 (2)
C16—O2—C13—C12	173.8 (2)	C11—C10—C15—C14	0.9 (3)
C16—O2—C13—C14	−6.0 (3)	C12—C11—C10—C7	179.69 (19)
C3—C2—C1—C6	−1.5 (4)	C12—C11—C10—C15	−1.0 (3)
C3—C2—C1—F	178.3 (3)	C10—C11—C12—C13	0.5 (3)
C4—C3—C2—C1	1.2 (4)	C11—C12—C13—O2	−179.71 (19)
N1—C4—C3—C2	−176.6 (2)	C11—C12—C13—C14	0.1 (3)
C5—C4—C3—C2	−0.4 (3)	O2—C13—C14—C15	179.7 (2)
N1—C4—C5—C6	175.7 (2)	C12—C13—C14—C15	−0.1 (4)
C3—C4—C5—C6	−0.3 (3)	C13—C14—C15—C10	−0.4 (4)

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···Cg1iv	0.93	2.89	3.801 (3)	167

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⋯Cg1iv	0.93	2.89	3.801 (3)	167

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