1-Acetyl-3-(4-chloro-phen-yl)-5-(4-fluoro-phen-yl)-2-pyrazoline.

In the title mol-ecule, C(17)H(14)ClFN(2)O, the mean plane of the pyrazoline ring makes dihedral angles of 18.19 (1) and 83.51 (4)° with the 4-chloro-benzene and 4-fluoro-benzene rings, respectively. The two benzene rings make a dihedral angle of 76.11 (2)°. Weak inter-molecular C-H⋯O hydrogen bonds help stabilize the crystal structure.

Related literature

For related literature, see: Dhal et al. (1975 ▶); Fahrni et al. (2003 ▶); Kimura et al. (1977 ▶); Lombardino & Ottemes (1981 ▶); Manna et al. (2002 ▶); Rawal et al. (1963 ▶).

Experimental

Crystal data

C17H14ClFN2O

M = 316.75

Monoclinic,

a = 14.5425 (19) Å

b = 11.3580 (14) Å

c = 9.6494 (13) Å

β = 108.154 (2)°

V = 1514.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 273 (2) K

0.14 × 0.12 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

7793 measured reflections

2676 independent reflections

2077 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.03

2676 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536808018333/at2570sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018333/at2570Isup2.hkl

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

C17H14ClFN2O	F000 = 656
Mr = 316.75	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2887 reflections
a = 14.5425 (19) Å	θ = 2.9–25.9º
b = 11.3580 (14) Å	µ = 0.27 mm−1
c = 9.6494 (13) Å	T = 273 (2) K
β = 108.154 (2)º	Bar, colourless
V = 1514.5 (3) Å3	0.14 × 0.12 × 0.06 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2077 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Monochromator: graphite	θmax = 25.1º
T = 273(2) K	θmin = 2.3º
φ and ω scans	h = −17→17
Absorption correction: none	k = −13→11
7793 measured reflections	l = −11→9
2676 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.4849P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.20 e Å−3
2676 reflections	Δρmin = −0.21 e Å−3
200 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (10)
Secondary atom site location: difference Fourier map

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
Cl1	0.45884 (5)	0.34606 (6)	0.02764 (8)	0.0949 (3)
F1	0.70769 (11)	−0.14714 (11)	1.10898 (14)	0.0851 (4)
O1	1.00066 (10)	−0.13914 (13)	0.72130 (15)	0.0685 (4)
N1	0.88095 (10)	−0.02205 (13)	0.59652 (15)	0.0491 (4)
N2	0.80952 (10)	0.00960 (13)	0.46876 (15)	0.0477 (4)
C1	0.93307 (15)	−0.17908 (18)	0.4668 (2)	0.0610 (5)
H1A	0.9661	−0.1361	0.4109	0.092*
H1B	0.8660	−0.1873	0.4111	0.092*
H1C	0.9617	−0.2557	0.4898	0.092*
C2	0.94144 (13)	−0.11419 (16)	0.6044 (2)	0.0494 (4)
C3	0.88134 (13)	0.05353 (16)	0.72122 (18)	0.0477 (4)
H3	0.9474	0.0797	0.7730	0.057*
C4	0.82018 (14)	0.15743 (16)	0.64155 (19)	0.0500 (5)
H4A	0.7728	0.1808	0.6881	0.060*
H4B	0.8604	0.2246	0.6373	0.060*
C5	0.77233 (12)	0.10719 (16)	0.49247 (18)	0.0454 (4)
C6	0.83785 (12)	−0.00700 (15)	0.82540 (18)	0.0446 (4)
C7	0.76197 (13)	−0.08590 (17)	0.7766 (2)	0.0530 (5)
H7	0.7404	−0.1070	0.6786	0.064*
C8	0.71794 (15)	−0.13366 (18)	0.8711 (2)	0.0593 (5)
H8	0.6671	−0.1868	0.8382	0.071*
C9	0.75105 (15)	−0.10081 (18)	1.0151 (2)	0.0574 (5)
C10	0.82613 (14)	−0.02457 (17)	1.0681 (2)	0.0537 (5)
H10	0.8474	−0.0044	1.1664	0.064*
C11	0.86977 (13)	0.02200 (16)	0.97206 (18)	0.0481 (4)
H11	0.9215	0.0737	1.0065	0.058*
C12	0.69236 (12)	0.16303 (16)	0.37998 (19)	0.0455 (4)
C13	0.63734 (14)	0.10150 (18)	0.2576 (2)	0.0557 (5)
H13	0.6499	0.0222	0.2473	0.067*
C14	0.56443 (15)	0.15720 (19)	0.1515 (2)	0.0621 (5)
H14	0.5275	0.1154	0.0703	0.075*
C15	0.54634 (13)	0.27427 (18)	0.1657 (2)	0.0588 (5)
C16	0.59780 (14)	0.33572 (18)	0.2860 (3)	0.0630 (6)
H16	0.5842	0.4147	0.2957	0.076*
C17	0.67020 (14)	0.28007 (17)	0.3936 (2)	0.0558 (5)
H17	0.7046	0.3218	0.4764	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0695 (4)	0.0900 (5)	0.1055 (5)	0.0056 (3)	−0.0012 (3)	0.0364 (4)
F1	0.1184 (11)	0.0792 (9)	0.0750 (9)	−0.0204 (8)	0.0552 (8)	0.0010 (7)
O1	0.0622 (9)	0.0758 (10)	0.0578 (9)	0.0125 (7)	0.0045 (7)	0.0014 (7)
N1	0.0505 (8)	0.0581 (9)	0.0370 (8)	0.0056 (7)	0.0111 (7)	−0.0052 (7)
N2	0.0485 (8)	0.0565 (9)	0.0372 (8)	0.0015 (7)	0.0121 (6)	−0.0026 (7)
C1	0.0680 (13)	0.0577 (12)	0.0615 (12)	0.0051 (10)	0.0261 (10)	−0.0078 (10)
C2	0.0464 (10)	0.0528 (11)	0.0501 (11)	−0.0025 (9)	0.0167 (9)	0.0005 (9)
C3	0.0456 (10)	0.0571 (11)	0.0393 (9)	−0.0055 (8)	0.0115 (8)	−0.0086 (8)
C4	0.0573 (11)	0.0502 (11)	0.0437 (10)	−0.0045 (9)	0.0177 (8)	−0.0045 (8)
C5	0.0474 (10)	0.0504 (11)	0.0413 (9)	−0.0051 (8)	0.0180 (8)	−0.0026 (8)
C6	0.0431 (9)	0.0497 (10)	0.0381 (9)	0.0034 (8)	0.0084 (7)	−0.0024 (8)
C7	0.0529 (11)	0.0613 (12)	0.0416 (10)	−0.0062 (9)	0.0098 (8)	−0.0067 (9)
C8	0.0599 (12)	0.0570 (12)	0.0623 (13)	−0.0115 (10)	0.0209 (10)	−0.0044 (10)
C9	0.0710 (13)	0.0546 (12)	0.0542 (12)	0.0017 (10)	0.0302 (10)	0.0049 (9)
C10	0.0666 (12)	0.0541 (11)	0.0388 (10)	0.0037 (10)	0.0142 (9)	−0.0018 (8)
C11	0.0487 (10)	0.0498 (10)	0.0416 (10)	0.0001 (8)	0.0078 (8)	−0.0043 (8)
C12	0.0452 (10)	0.0504 (11)	0.0441 (10)	−0.0035 (8)	0.0188 (8)	0.0003 (8)
C13	0.0609 (12)	0.0519 (11)	0.0513 (11)	−0.0008 (9)	0.0131 (9)	−0.0012 (9)
C14	0.0592 (12)	0.0677 (14)	0.0526 (12)	−0.0076 (10)	0.0075 (10)	0.0003 (10)
C15	0.0450 (11)	0.0608 (13)	0.0685 (13)	−0.0036 (9)	0.0144 (9)	0.0141 (10)
C16	0.0534 (12)	0.0488 (11)	0.0880 (16)	0.0000 (9)	0.0238 (11)	0.0063 (11)
C17	0.0511 (11)	0.0532 (12)	0.0636 (12)	−0.0058 (9)	0.0183 (10)	−0.0062 (10)

Cl1—C15	1.733 (2)	C6—C7	1.385 (2)
F1—C9	1.361 (2)	C7—C8	1.378 (3)
O1—C2	1.220 (2)	C7—H7	0.9300
N1—C2	1.354 (2)	C8—C9	1.373 (3)
N1—N2	1.3893 (19)	C8—H8	0.9300
N1—C3	1.477 (2)	C9—C10	1.362 (3)
N2—C5	1.285 (2)	C10—C11	1.381 (3)
C1—C2	1.490 (3)	C10—H10	0.9300
C1—H1A	0.9600	C11—H11	0.9300
C1—H1B	0.9600	C12—C17	1.384 (3)
C1—H1C	0.9600	C12—C13	1.391 (3)
C3—C6	1.510 (2)	C13—C14	1.377 (3)
C3—C4	1.533 (3)	C13—H13	0.9300
C3—H3	0.9800	C14—C15	1.371 (3)
C4—C5	1.502 (2)	C14—H14	0.9300
C4—H4A	0.9700	C15—C16	1.362 (3)
C4—H4B	0.9700	C16—C17	1.380 (3)
C5—C12	1.465 (2)	C16—H16	0.9300
C6—C11	1.385 (2)	C17—H17	0.9300
C2—N1—N2	122.87 (14)	C8—C7—H7	119.5
C2—N1—C3	124.48 (15)	C6—C7—H7	119.5
N2—N1—C3	112.62 (14)	C9—C8—C7	118.28 (18)
C5—N2—N1	107.76 (14)	C9—C8—H8	120.9
C2—C1—H1A	109.5	C7—C8—H8	120.9
C2—C1—H1B	109.5	F1—C9—C10	118.61 (18)
H1A—C1—H1B	109.5	F1—C9—C8	118.66 (19)
C2—C1—H1C	109.5	C10—C9—C8	122.73 (18)
H1A—C1—H1C	109.5	C9—C10—C11	118.23 (17)
H1B—C1—H1C	109.5	C9—C10—H10	120.9
O1—C2—N1	119.36 (17)	C11—C10—H10	120.9
O1—C2—C1	123.17 (18)	C10—C11—C6	121.12 (17)
N1—C2—C1	117.46 (17)	C10—C11—H11	119.4
N1—C3—C6	112.45 (15)	C6—C11—H11	119.4
N1—C3—C4	100.64 (13)	C17—C12—C13	118.28 (18)
C6—C3—C4	112.75 (14)	C17—C12—C5	120.02 (17)
N1—C3—H3	110.2	C13—C12—C5	121.70 (17)
C6—C3—H3	110.2	C14—C13—C12	120.43 (19)
C4—C3—H3	110.2	C14—C13—H13	119.8
C5—C4—C3	102.19 (14)	C12—C13—H13	119.8
C5—C4—H4A	111.3	C15—C14—C13	119.92 (19)
C3—C4—H4A	111.3	C15—C14—H14	120.0
C5—C4—H4B	111.3	C13—C14—H14	120.0
C3—C4—H4B	111.3	C16—C15—C14	120.72 (19)
H4A—C4—H4B	109.2	C16—C15—Cl1	119.42 (17)
N2—C5—C12	121.50 (16)	C14—C15—Cl1	119.84 (17)
N2—C5—C4	113.79 (16)	C15—C16—C17	119.62 (19)
C12—C5—C4	124.69 (16)	C15—C16—H16	120.2
C11—C6—C7	118.63 (17)	C17—C16—H16	120.2
C11—C6—C3	119.71 (16)	C16—C17—C12	120.97 (19)
C7—C6—C3	121.53 (15)	C16—C17—H17	119.5
C8—C7—C6	120.99 (17)	C12—C17—H17	119.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1i	0.97	2.57	3.425 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O1i	0.97	2.57	3.425 (2)	147

Symmetry code: (i) .