4-(4-Fluoro­phen­yl)-3-(4-pyrid­yl)quinolin-2(1H)-one

The title compound, C₂₀H₁₃FN₂O, has the quinolin-2(1H)-one unit in the lactam form. The mol­ecules form dimers via N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.174
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT751_ALERT_4_C Bond    Calc     0.90000, Rep   0.897(14) ......  Senseless su
              N8   -H8      1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.90000, Rep   0.897(14) ......  Senseless su
              N8   -H8      1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     1.92000, Rep   1.919(14) ......  Senseless su
              H8   -O1      1.555   2.655

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

4-(4-Fluorophenyl)-3-(4-pyridyl)quinolin-2(1H)-one

Crystal data

C20H13FN2O	F(000) = 1312
Mr = 316.33	Dx = 1.358 Mg m^−3
Monoclinic, C2/c	Melting point: 319 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54178 Å
a = 27.771 (2) Å	Cell parameters from 25 reflections
b = 8.2247 (4) Å	θ = 65–72°
c = 15.2643 (12) Å	µ = 0.76 mm^−1
β = 117.466 (3)°	T = 295 K
V = 3093.5 (4) Å^3	Plate, yellow
Z = 8	0.55 × 0.50 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2826 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.030
Graphite monochromator	θmax = 73.9°, θmin = 3.6°
θ/2ω scans	h = −34→30
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = 0→10
Tmin = 0.687, Tmax = 0.894	l = 0→19
3264 measured reflections	3 standard reflections every 60 min
3135 independent reflections	intensity decay: 5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.1237P)^2 + 1.2501P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
3135 reflections	Δρmax = 0.38 e Å^−3
232 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.29294 (5)	0.2471 (2)	0.63060 (9)	0.0816 (5)
O1	0.42966 (5)	0.27915 (19)	0.21389 (9)	0.0585 (4)
C1	0.42644 (6)	0.25966 (18)	0.44697 (11)	0.0398 (4)
C2	0.48386 (7)	0.23937 (19)	0.51099 (11)	0.0439 (4)
C3	0.50622 (8)	0.2110 (3)	0.61374 (13)	0.0571 (5)
H3	0.4835	0.2054	0.6432	0.062 (6)*
C4	0.56127 (8)	0.1916 (3)	0.67047 (13)	0.0650 (5)
H4	0.5754	0.1719	0.7378	0.082 (7)*
C5	0.59593 (7)	0.2010 (3)	0.62839 (14)	0.0598 (5)
H5	0.6332	0.1912	0.6679	0.079 (7)*
C6	0.57554 (7)	0.2250 (2)	0.52823 (13)	0.0515 (4)
H6	0.5988	0.2298	0.4998	0.070 (7)*
C7	0.51958 (6)	0.24196 (19)	0.46970 (12)	0.0431 (4)
N8	0.49841 (6)	0.25988 (17)	0.36863 (10)	0.0457 (4)
H8	0.5207 (5)	0.26244 (19)	0.3409 (7)	0.046 (5)*
C9	0.44483 (7)	0.2697 (2)	0.30442 (12)	0.0445 (4)
C10	0.40717 (6)	0.27215 (18)	0.34660 (11)	0.0399 (4)
C11	0.38924 (6)	0.26065 (18)	0.49260 (10)	0.0388 (4)
C12	0.39101 (7)	0.3868 (2)	0.55474 (12)	0.0494 (4)
H12	0.4150	0.4726	0.5664	0.062 (6)*
C13	0.35745 (8)	0.3861 (2)	0.59946 (12)	0.0554 (4)
H13	0.3580	0.4718	0.6397	0.077 (7)*
C14	0.32328 (7)	0.2554 (2)	0.58289 (12)	0.0517 (4)
C15	0.32041 (7)	0.1305 (2)	0.52175 (11)	0.0497 (4)
H15	0.2967	0.0442	0.5111	0.072 (7)*
C16	0.35313 (6)	0.13386 (19)	0.47597 (10)	0.0420 (4)
H16	0.3510	0.0501	0.4334	0.045 (4)*
C17	0.34849 (6)	0.28856 (19)	0.27639 (10)	0.0387 (3)
C18	0.31624 (6)	0.4091 (2)	0.28628 (11)	0.0493 (4)
H18	0.3311	0.4834	0.3379	0.073 (7)*
C19	0.26214 (7)	0.4175 (3)	0.21898 (13)	0.0588 (5)
H19	0.2416	0.4998	0.2270	0.081 (7)*
N20	0.23713 (6)	0.3161 (2)	0.14309 (11)	0.0593 (4)
C21	0.26846 (7)	0.2025 (2)	0.13367 (12)	0.0540 (4)
H21	0.2524	0.1303	0.0811	0.072 (7)*
C22	0.32327 (6)	0.1841 (2)	0.19656 (11)	0.0469 (4)
H22	0.3430	0.1025	0.1855	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0713 (8)	0.1261 (12)	0.0640 (8)	0.0041 (7)	0.0453 (7)	−0.0003 (7)
O1	0.0471 (6)	0.0976 (10)	0.0351 (6)	0.0080 (6)	0.0226 (5)	0.0102 (6)
C1	0.0412 (8)	0.0454 (8)	0.0314 (7)	−0.0020 (6)	0.0156 (6)	−0.0006 (5)
C2	0.0423 (8)	0.0525 (9)	0.0319 (7)	−0.0019 (6)	0.0128 (6)	−0.0006 (6)
C3	0.0506 (9)	0.0817 (12)	0.0339 (8)	0.0016 (8)	0.0152 (7)	0.0004 (8)
C4	0.0550 (10)	0.0904 (14)	0.0342 (8)	0.0046 (10)	0.0073 (7)	−0.0003 (8)
C5	0.0421 (8)	0.0698 (11)	0.0499 (10)	0.0057 (8)	0.0062 (7)	−0.0007 (8)
C6	0.0411 (8)	0.0578 (9)	0.0516 (9)	0.0019 (7)	0.0179 (7)	0.0016 (7)
C7	0.0417 (8)	0.0467 (8)	0.0379 (8)	−0.0004 (6)	0.0159 (6)	0.0011 (6)
N8	0.0400 (7)	0.0614 (8)	0.0387 (7)	0.0025 (5)	0.0208 (6)	0.0048 (6)
C9	0.0425 (8)	0.0561 (9)	0.0365 (7)	0.0033 (6)	0.0198 (6)	0.0054 (6)
C10	0.0400 (8)	0.0479 (8)	0.0320 (7)	0.0011 (6)	0.0168 (6)	0.0019 (5)
C11	0.0402 (7)	0.0465 (8)	0.0270 (6)	0.0004 (6)	0.0133 (6)	0.0008 (5)
C12	0.0585 (9)	0.0491 (9)	0.0408 (8)	−0.0085 (7)	0.0230 (7)	−0.0087 (6)
C13	0.0652 (10)	0.0619 (10)	0.0428 (8)	0.0042 (8)	0.0281 (8)	−0.0110 (7)
C14	0.0462 (8)	0.0754 (11)	0.0352 (8)	0.0068 (7)	0.0203 (7)	0.0051 (7)
C15	0.0458 (8)	0.0603 (10)	0.0400 (8)	−0.0065 (7)	0.0171 (6)	0.0043 (7)
C16	0.0456 (8)	0.0443 (8)	0.0317 (7)	−0.0004 (6)	0.0142 (6)	−0.0013 (5)
C17	0.0397 (7)	0.0483 (8)	0.0294 (7)	0.0025 (6)	0.0172 (6)	0.0060 (5)
C18	0.0502 (9)	0.0565 (9)	0.0393 (8)	0.0078 (7)	0.0189 (7)	−0.0009 (7)
C19	0.0521 (9)	0.0701 (11)	0.0500 (9)	0.0190 (8)	0.0198 (8)	0.0017 (8)
N20	0.0454 (7)	0.0775 (11)	0.0444 (8)	0.0112 (7)	0.0118 (6)	0.0029 (7)
C21	0.0479 (9)	0.0669 (10)	0.0389 (8)	0.0005 (8)	0.0131 (7)	−0.0051 (7)
C22	0.0464 (8)	0.0551 (9)	0.0369 (7)	0.0047 (7)	0.0171 (7)	−0.0021 (6)

Geometric parameters (Å, º)

F1—C14	1.346 (2)	C11—C16	1.387 (2)
O1—C9	1.2474 (19)	C11—C12	1.391 (2)
C1—C10	1.374 (2)	C12—C13	1.386 (2)
C1—C2	1.445 (2)	C12—H12	0.9300
C1—C11	1.489 (2)	C13—C14	1.378 (3)
C2—C7	1.399 (2)	C13—H13	0.9300
C2—C3	1.415 (2)	C14—C15	1.366 (3)
C3—C4	1.375 (3)	C15—C16	1.379 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.384 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C22	1.388 (2)
C5—C6	1.378 (3)	C17—C18	1.390 (2)
C5—H5	0.9300	C18—C19	1.376 (2)
C6—C7	1.397 (2)	C18—H18	0.9300
C6—H6	0.9300	C19—N20	1.333 (3)
C7—N8	1.382 (2)	C19—H19	0.9300
N8—C9	1.355 (2)	N20—C21	1.329 (3)
N8—H8	0.897 (14)	C21—C22	1.383 (2)
C9—C10	1.460 (2)	C21—H21	0.9300
C10—C17	1.487 (2)	C22—H22	0.9300
C10—C1—C2	120.22 (14)	C12—C11—C1	120.61 (14)
C10—C1—C11	121.60 (14)	C13—C12—C11	120.83 (15)
C2—C1—C11	118.15 (13)	C13—C12—H12	119.6
C7—C2—C3	117.52 (15)	C11—C12—H12	119.6
C7—C2—C1	118.95 (14)	C14—C13—C12	118.36 (15)
C3—C2—C1	123.49 (15)	C14—C13—H13	120.8
C4—C3—C2	120.61 (18)	C12—C13—H13	120.8
C4—C3—H3	119.7	F1—C14—C15	118.55 (17)
C2—C3—H3	119.7	F1—C14—C13	119.36 (16)
C3—C4—C5	120.68 (17)	C15—C14—C13	122.06 (15)
C3—C4—H4	119.7	C14—C15—C16	119.13 (15)
C5—C4—H4	119.7	C14—C15—H15	120.4
C6—C5—C4	120.34 (16)	C16—C15—H15	120.4
C6—C5—H5	119.8	C15—C16—C11	120.83 (14)
C4—C5—H5	119.8	C15—C16—H16	119.6
C5—C6—C7	119.38 (17)	C11—C16—H16	119.6
C5—C6—H6	120.3	C22—C17—C18	116.57 (14)
C7—C6—H6	120.3	C22—C17—C10	121.20 (13)
N8—C7—C6	119.97 (15)	C18—C17—C10	122.22 (14)
N8—C7—C2	118.64 (14)	C19—C18—C17	119.40 (16)
C6—C7—C2	121.39 (15)	C19—C18—H18	120.3
C9—N8—C7	125.00 (13)	C17—C18—H18	120.3
C9—N8—H8	115.1	N20—C19—C18	124.70 (16)
C7—N8—H8	119.8	N20—C19—H19	117.7
O1—C9—N8	120.14 (14)	C18—C19—H19	117.7
O1—C9—C10	122.91 (15)	C21—N20—C19	115.40 (15)
N8—C9—C10	116.94 (14)	N20—C21—C22	124.59 (16)
C1—C10—C9	120.07 (15)	N20—C21—H21	117.7
C1—C10—C17	122.97 (13)	C22—C21—H21	117.7
C9—C10—C17	116.96 (13)	C21—C22—C17	119.31 (15)
C16—C11—C12	118.74 (14)	C21—C22—H22	120.3
C16—C11—C1	120.63 (13)	C17—C22—H22	120.3
C10—C1—C2—C7	3.6 (2)	C10—C1—C11—C16	66.5 (2)
C11—C1—C2—C7	−178.51 (14)	C2—C1—C11—C16	−111.33 (16)
C10—C1—C2—C3	−174.08 (17)	C10—C1—C11—C12	−115.08 (17)
C11—C1—C2—C3	3.8 (2)	C2—C1—C11—C12	67.04 (19)
C7—C2—C3—C4	1.8 (3)	C16—C11—C12—C13	0.1 (2)
C1—C2—C3—C4	179.54 (18)	C1—C11—C12—C13	−178.30 (15)
C2—C3—C4—C5	0.6 (3)	C11—C12—C13—C14	1.6 (3)
C3—C4—C5—C6	−2.1 (3)	C12—C13—C14—F1	175.70 (16)
C4—C5—C6—C7	0.9 (3)	C12—C13—C14—C15	−2.1 (3)
C5—C6—C7—N8	−177.55 (17)	F1—C14—C15—C16	−177.05 (15)
C5—C6—C7—C2	1.7 (3)	C13—C14—C15—C16	0.8 (3)
C3—C2—C7—N8	176.23 (16)	C14—C15—C16—C11	1.1 (2)
C1—C2—C7—N8	−1.6 (2)	C12—C11—C16—C15	−1.5 (2)
C3—C2—C7—C6	−3.0 (2)	C1—C11—C16—C15	176.92 (14)
C1—C2—C7—C6	179.19 (15)	C1—C10—C17—C22	−126.81 (17)
C6—C7—N8—C9	176.79 (16)	C9—C10—C17—C22	53.2 (2)
C2—C7—N8—C9	−2.5 (2)	C1—C10—C17—C18	53.8 (2)
C7—N8—C9—O1	−177.07 (16)	C9—C10—C17—C18	−126.14 (16)
C7—N8—C9—C10	4.2 (2)	C22—C17—C18—C19	0.8 (2)
C2—C1—C10—C9	−1.8 (2)	C10—C17—C18—C19	−179.80 (15)
C11—C1—C10—C9	−179.61 (13)	C17—C18—C19—N20	0.5 (3)
C2—C1—C10—C17	178.25 (14)	C18—C19—N20—C21	−1.2 (3)
C11—C1—C10—C17	0.4 (2)	C19—N20—C21—C22	0.6 (3)
O1—C9—C10—C1	179.36 (16)	N20—C21—C22—C17	0.6 (3)
N8—C9—C10—C1	−2.0 (2)	C18—C17—C22—C21	−1.3 (2)
O1—C9—C10—C17	−0.7 (2)	C10—C17—C22—C21	179.28 (15)
N8—C9—C10—C17	177.99 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1^i	0.90 (1)	1.92 (1)	2.8148 (18)	177

Symmetry code: (i) −x+1, y, −z+1/2.