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

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

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.047
• wR factor = 0.125
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

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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., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2005); software used to prepare material for publication: SHELXL97.

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

Crystal data

C20H13FN2O	F(000) = 656
Mr = 316.33	Dx = 1.350 Mg m^−3
Monoclinic, P21/n	Melting point: 352 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 9.434 (5) Å	Cell parameters from 25 reflections
b = 9.9087 (16) Å	θ = 27–49°
c = 16.789 (9) Å	µ = 0.76 mm^−1
β = 97.32 (3)°	T = 193 K
V = 1556.7 (12) Å^3	Needle, colourless
Z = 4	0.32 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: rotating anode	θmax = 69.9°, θmin = 5.1°
Graphite monochromator	h = −11→0
θ/2ω scans	k = 0→12
2956 measured reflections	l = −19→20
2956 independent reflections	3 standard reflections every 60 min
2184 reflections with I > 2σ(I)	intensity decay: 4%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	Only H-atom displacement parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.4397P] where P = (Fo^2 + 2Fc^2)/3
2956 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−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
C1	0.29496 (19)	0.42242 (19)	0.55496 (11)	0.0208 (4)
C2	0.3045 (2)	0.27356 (19)	0.55621 (11)	0.0224 (4)
N3	0.25406 (17)	0.21014 (16)	0.48615 (9)	0.0236 (4)
H3	0.25527 (18)	0.115 (3)	0.48743 (10)	0.039 (7)*
C4	0.1953 (2)	0.27336 (19)	0.41653 (11)	0.0220 (4)
C5	0.1412 (2)	0.1964 (2)	0.34938 (12)	0.0290 (5)
H5	0.1478	0.1008	0.3510	0.032 (6)*
C6	0.0785 (2)	0.2602 (2)	0.28120 (12)	0.0327 (5)
H6	0.0405	0.2083	0.2359	0.045 (7)*
C7	0.0703 (2)	0.4006 (2)	0.27804 (12)	0.0343 (5)
H7	0.0268	0.4437	0.2306	0.051 (7)*
C8	0.1246 (2)	0.4771 (2)	0.34295 (12)	0.0282 (5)
H8	0.1188	0.5727	0.3400	0.026 (6)*
C9	0.1888 (2)	0.41482 (19)	0.41394 (11)	0.0218 (4)
C10	0.2420 (2)	0.48844 (18)	0.48621 (11)	0.0206 (4)
O11	0.35715 (15)	0.20885 (14)	0.61519 (8)	0.0287 (3)
C12	0.3475 (2)	0.49290 (18)	0.63144 (11)	0.0224 (4)
C13	0.2802 (2)	0.4700 (2)	0.69923 (12)	0.0287 (4)
H13	0.2039	0.4070	0.6968	0.033 (6)*
C14	0.3232 (2)	0.5381 (2)	0.77044 (13)	0.0342 (5)
H14	0.2753	0.5250	0.8163	0.044 (7)*
C15	0.4371 (2)	0.6249 (2)	0.77272 (13)	0.0337 (5)
C16	0.5078 (2)	0.6492 (2)	0.70795 (13)	0.0359 (5)
H16	0.5865	0.7097	0.7117	0.050 (8)*
C17	0.4612 (2)	0.5828 (2)	0.63641 (12)	0.0286 (4)
H17	0.5077	0.5991	0.5904	0.033 (6)*
F18	0.48079 (16)	0.69101 (16)	0.84278 (8)	0.0518 (4)
C19	0.2380 (2)	0.63916 (18)	0.48439 (11)	0.0214 (4)
C20	0.3256 (2)	0.7110 (2)	0.43904 (12)	0.0282 (4)
H20	0.3859	0.6649	0.4069	0.038 (6)*
C21	0.3238 (3)	0.8503 (2)	0.44134 (13)	0.0349 (5)
H21	0.3863	0.8982	0.4113	0.041 (7)*
N22	0.2390 (2)	0.92114 (17)	0.48359 (11)	0.0335 (4)
C23	0.1533 (2)	0.8513 (2)	0.52571 (13)	0.0312 (5)
H23	0.0910	0.9001	0.5554	0.036 (6)*
C24	0.1498 (2)	0.7117 (2)	0.52857 (12)	0.0271 (4)
H24	0.0881	0.6666	0.5603	0.041 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0223 (9)	0.0186 (9)	0.0211 (9)	−0.0015 (7)	0.0015 (7)	−0.0014 (7)
C2	0.0246 (9)	0.0186 (9)	0.0238 (9)	−0.0027 (8)	0.0017 (7)	0.0013 (8)
N3	0.0328 (9)	0.0121 (7)	0.0247 (8)	−0.0001 (7)	−0.0012 (7)	−0.0008 (6)
C4	0.0241 (9)	0.0190 (9)	0.0226 (9)	−0.0014 (8)	0.0013 (7)	−0.0003 (7)
C5	0.0343 (11)	0.0228 (10)	0.0293 (11)	−0.0050 (9)	0.0013 (9)	−0.0053 (8)
C6	0.0352 (12)	0.0373 (12)	0.0235 (10)	−0.0048 (10)	−0.0039 (9)	−0.0079 (9)
C7	0.0388 (12)	0.0374 (12)	0.0240 (10)	0.0015 (10)	−0.0065 (9)	0.0022 (9)
C8	0.0324 (11)	0.0235 (10)	0.0268 (10)	0.0018 (9)	−0.0036 (8)	0.0030 (8)
C9	0.0230 (9)	0.0200 (9)	0.0217 (9)	0.0001 (8)	0.0007 (7)	0.0003 (7)
C10	0.0217 (9)	0.0160 (9)	0.0244 (9)	0.0000 (7)	0.0035 (7)	0.0002 (7)
O11	0.0380 (8)	0.0216 (7)	0.0247 (7)	−0.0003 (6)	−0.0034 (6)	0.0065 (6)
C12	0.0264 (10)	0.0156 (9)	0.0240 (10)	0.0026 (8)	−0.0017 (8)	−0.0015 (7)
C13	0.0314 (11)	0.0266 (10)	0.0274 (10)	−0.0007 (9)	0.0011 (8)	−0.0005 (8)
C14	0.0403 (13)	0.0358 (12)	0.0261 (11)	0.0047 (10)	0.0028 (9)	−0.0027 (9)
C15	0.0369 (12)	0.0320 (11)	0.0287 (11)	0.0063 (10)	−0.0093 (9)	−0.0135 (9)
C16	0.0307 (12)	0.0350 (12)	0.0400 (12)	−0.0077 (10)	−0.0033 (9)	−0.0097 (10)
C17	0.0289 (10)	0.0277 (11)	0.0283 (10)	−0.0028 (9)	0.0003 (8)	−0.0026 (9)
F18	0.0557 (9)	0.0598 (10)	0.0356 (7)	−0.0017 (7)	−0.0102 (6)	−0.0252 (7)
C19	0.0250 (10)	0.0158 (9)	0.0218 (9)	0.0001 (7)	−0.0029 (7)	−0.0003 (7)
C20	0.0349 (11)	0.0199 (10)	0.0310 (11)	0.0018 (8)	0.0088 (9)	0.0005 (8)
C21	0.0441 (13)	0.0220 (11)	0.0394 (12)	−0.0039 (9)	0.0090 (10)	0.0044 (9)
N22	0.0459 (11)	0.0166 (8)	0.0371 (10)	0.0006 (8)	0.0020 (8)	0.0000 (8)
C23	0.0406 (12)	0.0205 (10)	0.0329 (11)	0.0053 (9)	0.0061 (9)	−0.0034 (8)
C24	0.0318 (11)	0.0198 (10)	0.0303 (10)	0.0012 (8)	0.0064 (8)	0.0001 (8)

Geometric parameters (Å, º)

C1—C10	1.365 (3)	C16—C17	1.391 (3)
C1—C2	1.478 (3)	C19—C24	1.384 (3)
C1—C12	1.490 (3)	C19—C20	1.389 (3)
C2—O11	1.230 (2)	C20—C21	1.381 (3)
C2—N3	1.365 (2)	C21—N22	1.335 (3)
N3—C4	1.378 (2)	N22—C23	1.334 (3)
C4—C5	1.402 (3)	C23—C24	1.384 (3)
C4—C9	1.404 (3)	N3—H3	0.9400
C5—C6	1.373 (3)	C5—H5	0.9500
C6—C7	1.394 (3)	C6—H6	0.9500
C7—C8	1.372 (3)	C7—H7	0.9500
C8—C9	1.409 (3)	C8—H8	0.9500
C9—C10	1.449 (3)	C13—H13	0.9500
C10—C19	1.494 (2)	C14—H14	0.9500
C12—C17	1.389 (3)	C16—H16	0.9500
C12—C13	1.390 (3)	C17—H17	0.9500
C13—C14	1.388 (3)	C20—H20	0.9500
C14—C15	1.373 (3)	C21—H21	0.9500
C15—F18	1.363 (2)	C23—H23	0.9500
C15—C16	1.368 (3)	C24—H24	0.9500
C10—C1—C2	120.37 (17)	C20—C19—C10	120.54 (18)
C10—C1—C12	123.35 (17)	C21—C20—C19	119.1 (2)
C2—C1—C12	116.28 (16)	N22—C21—C20	123.4 (2)
O11—C2—N3	120.97 (18)	C23—N22—C21	117.00 (18)
O11—C2—C1	123.32 (17)	N22—C23—C24	123.7 (2)
N3—C2—C1	115.69 (16)	C23—C24—C19	118.8 (2)
C2—N3—C4	125.45 (16)	C4—N3—H3	118.00
N3—C4—C5	120.04 (18)	C2—N3—H3	116.00
N3—C4—C9	119.43 (17)	C4—C5—H5	120.00
C5—C4—C9	120.52 (18)	C6—C5—H5	120.00
C6—C5—C4	119.61 (19)	C5—C6—H6	120.00
C5—C6—C7	120.44 (19)	C7—C6—H6	120.00
C8—C7—C6	120.5 (2)	C6—C7—H7	120.00
C7—C8—C9	120.5 (2)	C8—C7—H7	120.00
C4—C9—C8	118.44 (18)	C7—C8—H8	120.00
C4—C9—C10	117.88 (17)	C9—C8—H8	120.00
C8—C9—C10	123.60 (18)	C12—C13—H13	120.00
C1—C10—C9	121.13 (17)	C14—C13—H13	120.00
C1—C10—C19	120.14 (17)	C13—C14—H14	121.00
C9—C10—C19	118.73 (17)	C15—C14—H14	121.00
C17—C12—C13	119.01 (18)	C15—C16—H16	121.00
C17—C12—C1	121.46 (18)	C17—C16—H16	121.00
C13—C12—C1	119.52 (18)	C12—C17—H17	120.00
C14—C13—C12	120.8 (2)	C16—C17—H17	120.00
C15—C14—C13	118.1 (2)	C19—C20—H20	120.00
F18—C15—C16	118.5 (2)	C21—C20—H20	120.00
F18—C15—C14	118.3 (2)	N22—C21—H21	118.00
C16—C15—C14	123.2 (2)	C20—C21—H21	118.00
C15—C16—C17	118.1 (2)	N22—C23—H23	118.00
C12—C17—C16	120.8 (2)	C24—C23—H23	118.00
C24—C19—C20	117.87 (17)	C19—C24—H24	121.00
C24—C19—C10	121.58 (18)	C23—C24—H24	121.00
C10—C1—C2—O11	176.59 (18)	C10—C1—C12—C17	−60.9 (3)
C12—C1—C2—O11	−2.6 (3)	C2—C1—C12—C17	118.3 (2)
C10—C1—C2—N3	−1.7 (3)	C10—C1—C12—C13	118.2 (2)
C12—C1—C2—N3	179.03 (16)	C2—C1—C12—C13	−62.6 (2)
O11—C2—N3—C4	−178.96 (18)	C17—C12—C13—C14	1.6 (3)
C1—C2—N3—C4	−0.6 (3)	C1—C12—C13—C14	−177.52 (19)
C2—N3—C4—C5	−177.07 (19)	C12—C13—C14—C15	−2.2 (3)
C2—N3—C4—C9	2.2 (3)	C13—C14—C15—F18	−179.31 (19)
N3—C4—C5—C6	177.81 (19)	C13—C14—C15—C16	1.3 (3)
C9—C4—C5—C6	−1.4 (3)	F18—C15—C16—C17	−179.10 (19)
C4—C5—C6—C7	0.9 (3)	C14—C15—C16—C17	0.3 (3)
C5—C6—C7—C8	0.0 (4)	C13—C12—C17—C16	0.1 (3)
C6—C7—C8—C9	−0.3 (3)	C1—C12—C17—C16	179.14 (19)
N3—C4—C9—C8	−178.17 (17)	C15—C16—C17—C12	−1.0 (3)
C5—C4—C9—C8	1.0 (3)	C1—C10—C19—C24	−67.1 (3)
N3—C4—C9—C10	−1.4 (3)	C9—C10—C19—C24	112.9 (2)
C5—C4—C9—C10	177.84 (17)	C1—C10—C19—C20	111.6 (2)
C7—C8—C9—C4	−0.2 (3)	C9—C10—C19—C20	−68.4 (3)
C7—C8—C9—C10	−176.8 (2)	C24—C19—C20—C21	1.6 (3)
C2—C1—C10—C9	2.4 (3)	C10—C19—C20—C21	−177.2 (2)
C12—C1—C10—C9	−178.38 (18)	C19—C20—C21—N22	−1.8 (4)
C2—C1—C10—C19	−177.56 (17)	C20—C21—N22—C23	0.5 (3)
C12—C1—C10—C19	1.6 (3)	C21—N22—C23—C24	1.0 (3)
C4—C9—C10—C1	−0.9 (3)	N22—C23—C24—C19	−1.2 (3)
C8—C9—C10—C1	175.74 (19)	C20—C19—C24—C23	−0.2 (3)
C4—C9—C10—C19	179.13 (18)	C10—C19—C24—C23	178.61 (19)
C8—C9—C10—C19	−4.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N22^i	0.94	1.93	2.867 (2)	174

Symmetry code: (i) x, y−1, z.