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

The title compound, C₂₁H₁₅FN₂O, was synthesized in the course of our studies of p38 mitogen-activated protein kinase inhibitors. It has been investigated by ¹H and ¹³C NMR spectroscopy and was proven by X-ray crystallographic analysis to be the N-methyl rather than the O-methyl isomer. In the crystal structure, a three-dimensional network is formed consisting of quinolinone aromatic stacking inter­actions and weak C—H...O and C—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.049
• wR factor = 0.164
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

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Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and SYBYL (Tripos Associates Inc., 1996); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

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

Crystal data

C21H15FN2O	F(000) = 688
Mr = 330.36	Dx = 1.354 Mg m^−3
Monoclinic, P21/n	Melting point: 524.7 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.3217 (6) Å	Cell parameters from 2517 reflections
b = 18.1539 (11) Å	θ = 2.4–30.3°
c = 9.9297 (7) Å	µ = 0.09 mm^−1
β = 105.259 (4)°	T = 193 K
V = 1621.12 (18) Å^3	Needle, colourless
Z = 4	0.49 × 0.24 × 0.09 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3895 independent reflections
Radiation source: sealed tube	2765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω and φ scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (CORINC; Dräger & Gattow, 1971)	h = −12→11
Tmin = 0.939, Tmax = 0.992	k = −20→23
10801 measured reflections	l = −12→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0967P)^2 + 0.0759P] where P = (Fo^2 + 2Fc^2)/3
3895 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	0.28229 (17)	0.97326 (8)	0.75822 (17)	0.0220 (3)
C2	0.23088 (17)	1.04496 (9)	0.69529 (18)	0.0260 (4)
N3	0.33071 (14)	1.08487 (7)	0.64251 (15)	0.0245 (3)
C4	0.47674 (17)	1.06182 (8)	0.65352 (17)	0.0226 (3)
C5	0.57709 (19)	1.10673 (9)	0.60710 (18)	0.0290 (4)
H5	0.5469	1.1541	0.5695	0.035*
C6	0.71919 (19)	1.08205 (10)	0.61617 (19)	0.0316 (4)
H6	0.7860	1.1127	0.5842	0.038*
C7	0.76678 (18)	1.01292 (10)	0.67137 (19)	0.0307 (4)
H7	0.8643	0.9961	0.6752	0.037*
C8	0.67031 (18)	0.96948 (9)	0.72018 (18)	0.0268 (4)
H8	0.7029	0.9227	0.7592	0.032*
C9	0.52457 (17)	0.99268 (9)	0.71380 (17)	0.0223 (3)
C10	0.42156 (17)	0.94869 (8)	0.76635 (16)	0.0217 (3)
O11	0.10585 (13)	1.06895 (7)	0.68856 (16)	0.0411 (4)
C12	0.17411 (17)	0.92918 (8)	0.81275 (18)	0.0232 (3)
C13	0.09379 (19)	0.87252 (10)	0.73244 (19)	0.0300 (4)
H13	0.1040	0.8636	0.6412	0.036*
C14	−0.00143 (19)	0.82896 (10)	0.7855 (2)	0.0322 (4)
H14	−0.0570	0.7904	0.7311	0.039*
C15	−0.01331 (19)	0.84276 (10)	0.9170 (2)	0.0314 (4)
C16	0.0605 (2)	0.89897 (11)	0.9981 (2)	0.0412 (5)
H16	0.0476	0.9080	1.0884	0.049*
C17	0.1549 (2)	0.94257 (11)	0.9443 (2)	0.0369 (4)
H17	0.2070	0.9821	0.9985	0.044*
F18	−0.10398 (14)	0.79862 (7)	0.97014 (14)	0.0508 (4)
C19	0.47406 (17)	0.87620 (9)	0.83307 (17)	0.0228 (3)
C20	0.5448 (2)	0.87174 (10)	0.97321 (19)	0.0339 (4)
H20	0.5593	0.9147	1.0298	0.041*
C21	0.5947 (2)	0.80380 (10)	1.0310 (2)	0.0379 (5)
H21	0.6428	0.8019	1.1280	0.045*
N22	0.57944 (17)	0.74128 (8)	0.95892 (17)	0.0339 (4)
C23	0.5100 (2)	0.74613 (9)	0.8233 (2)	0.0336 (4)
H23	0.4965	0.7022	0.7695	0.040*
C24	0.4566 (2)	0.81133 (9)	0.75641 (19)	0.0296 (4)
H24	0.4086	0.8117	0.6593	0.036*
C25	0.2754 (2)	1.15245 (10)	0.5651 (2)	0.0332 (4)
H25A	0.3216	1.1953	0.6194	0.050*
H25B	0.1672	1.1552	0.5489	0.050*
H25C	0.3005	1.1519	0.4752	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0243 (8)	0.0202 (8)	0.0225 (8)	−0.0027 (6)	0.0079 (6)	−0.0031 (6)
C2	0.0250 (8)	0.0224 (8)	0.0311 (9)	0.0001 (6)	0.0085 (7)	−0.0015 (7)
N3	0.0262 (7)	0.0206 (7)	0.0275 (8)	0.0027 (5)	0.0085 (5)	0.0024 (6)
C4	0.0255 (8)	0.0213 (8)	0.0211 (8)	−0.0024 (6)	0.0063 (6)	−0.0033 (6)
C5	0.0344 (9)	0.0258 (9)	0.0280 (9)	−0.0051 (7)	0.0103 (7)	0.0011 (7)
C6	0.0310 (9)	0.0368 (10)	0.0300 (10)	−0.0117 (7)	0.0135 (7)	−0.0027 (8)
C7	0.0227 (8)	0.0398 (10)	0.0306 (10)	−0.0041 (7)	0.0086 (7)	−0.0052 (8)
C8	0.0249 (8)	0.0259 (8)	0.0295 (9)	−0.0003 (6)	0.0070 (6)	−0.0037 (7)
C9	0.0232 (7)	0.0212 (8)	0.0220 (8)	−0.0016 (6)	0.0052 (6)	−0.0032 (6)
C10	0.0263 (8)	0.0194 (7)	0.0201 (8)	−0.0014 (6)	0.0073 (6)	−0.0014 (6)
O11	0.0281 (7)	0.0314 (7)	0.0677 (10)	0.0078 (5)	0.0196 (6)	0.0113 (7)
C12	0.0223 (7)	0.0202 (8)	0.0277 (9)	0.0008 (6)	0.0077 (6)	−0.0006 (6)
C13	0.0323 (9)	0.0300 (9)	0.0301 (9)	−0.0047 (7)	0.0124 (7)	−0.0057 (7)
C14	0.0300 (9)	0.0269 (9)	0.0404 (11)	−0.0070 (7)	0.0104 (7)	−0.0042 (8)
C15	0.0279 (8)	0.0292 (9)	0.0400 (11)	−0.0025 (7)	0.0142 (7)	0.0084 (8)
C16	0.0495 (12)	0.0501 (12)	0.0292 (10)	−0.0121 (9)	0.0192 (9)	−0.0052 (9)
C17	0.0423 (10)	0.0385 (10)	0.0329 (10)	−0.0146 (8)	0.0155 (8)	−0.0111 (8)
F18	0.0510 (7)	0.0498 (7)	0.0596 (9)	−0.0166 (5)	0.0290 (6)	0.0087 (6)
C19	0.0228 (7)	0.0218 (8)	0.0259 (8)	−0.0005 (6)	0.0102 (6)	0.0013 (6)
C20	0.0438 (10)	0.0271 (9)	0.0290 (10)	0.0002 (7)	0.0063 (8)	−0.0032 (8)
C21	0.0476 (11)	0.0339 (10)	0.0297 (10)	0.0016 (8)	0.0059 (8)	0.0029 (8)
N22	0.0405 (9)	0.0263 (7)	0.0363 (9)	0.0011 (6)	0.0123 (7)	0.0072 (7)
C23	0.0468 (11)	0.0211 (8)	0.0349 (11)	0.0007 (7)	0.0142 (8)	−0.0005 (7)
C24	0.0403 (9)	0.0223 (8)	0.0257 (9)	−0.0009 (7)	0.0079 (7)	0.0002 (7)
C25	0.0390 (10)	0.0250 (8)	0.0356 (11)	0.0047 (7)	0.0095 (8)	0.0065 (7)

Geometric parameters (Å, º)

C1—C10	1.355 (2)	C13—H13	0.9500
C1—C2	1.469 (2)	C14—C15	1.363 (3)
C1—C12	1.496 (2)	C14—H14	0.9500
C2—O11	1.2294 (19)	C15—F18	1.3672 (19)
C2—N3	1.386 (2)	C15—C16	1.368 (3)
N3—C4	1.401 (2)	C16—C17	1.390 (3)
N3—C25	1.467 (2)	C16—H16	0.9500
C4—C5	1.407 (2)	C17—H17	0.9500
C4—C9	1.411 (2)	C19—C20	1.377 (2)
C5—C6	1.379 (2)	C19—C24	1.388 (2)
C5—H5	0.9500	C20—C21	1.388 (3)
C6—C7	1.394 (3)	C20—H20	0.9500
C6—H6	0.9500	C21—N22	1.329 (2)
C7—C8	1.377 (2)	C21—H21	0.9500
C7—H7	0.9500	N22—C23	1.334 (2)
C8—C9	1.408 (2)	C23—C24	1.384 (2)
C8—H8	0.9500	C23—H23	0.9500
C9—C10	1.448 (2)	C24—H24	0.9500
C10—C19	1.496 (2)	C25—H25A	0.9800
C12—C17	1.386 (3)	C25—H25B	0.9800
C12—C13	1.393 (2)	C25—H25C	0.9800
C13—C14	1.392 (2)
C10—C1—C2	121.16 (14)	C12—C13—H13	119.9
C10—C1—C12	121.93 (14)	C15—C14—C13	118.63 (16)
C2—C1—C12	116.91 (13)	C15—C14—H14	120.7
O11—C2—N3	121.02 (15)	C13—C14—H14	120.7
O11—C2—C1	122.38 (15)	C14—C15—F18	118.46 (16)
N3—C2—C1	116.60 (13)	C14—C15—C16	123.09 (16)
C2—N3—C4	123.34 (13)	F18—C15—C16	118.44 (17)
C2—N3—C25	117.19 (13)	C15—C16—C17	118.03 (18)
C4—N3—C25	119.38 (14)	C15—C16—H16	121.0
N3—C4—C5	121.18 (14)	C17—C16—H16	121.0
N3—C4—C9	119.40 (14)	C12—C17—C16	120.91 (17)
C5—C4—C9	119.42 (15)	C12—C17—H17	119.5
C6—C5—C4	120.04 (16)	C16—C17—H17	119.5
C6—C5—H5	120.0	C20—C19—C24	117.40 (15)
C4—C5—H5	120.0	C20—C19—C10	120.87 (15)
C5—C6—C7	121.26 (15)	C24—C19—C10	121.71 (15)
C5—C6—H6	119.4	C19—C20—C21	119.32 (16)
C7—C6—H6	119.4	C19—C20—H20	120.3
C8—C7—C6	118.97 (16)	C21—C20—H20	120.3
C8—C7—H7	120.5	N22—C21—C20	123.98 (18)
C6—C7—H7	120.5	N22—C21—H21	118.0
C7—C8—C9	121.66 (16)	C20—C21—H21	118.0
C7—C8—H8	119.2	C21—N22—C23	116.23 (15)
C9—C8—H8	119.2	N22—C23—C24	123.94 (16)
C8—C9—C4	118.59 (15)	N22—C23—H23	118.0
C8—C9—C10	122.85 (15)	C24—C23—H23	118.0
C4—C9—C10	118.55 (14)	C23—C24—C19	119.12 (16)
C1—C10—C9	120.86 (14)	C23—C24—H24	120.4
C1—C10—C19	120.83 (14)	C19—C24—H24	120.4
C9—C10—C19	118.30 (13)	N3—C25—H25A	109.5
C17—C12—C13	119.07 (15)	N3—C25—H25B	109.5
C17—C12—C1	120.92 (14)	H25A—C25—H25B	109.5
C13—C12—C1	119.99 (15)	N3—C25—H25C	109.5
C14—C13—C12	120.21 (17)	H25A—C25—H25C	109.5
C14—C13—H13	119.9	H25B—C25—H25C	109.5
C10—C1—C2—O11	−178.90 (17)	C8—C9—C10—C19	1.4 (2)
C12—C1—C2—O11	1.0 (3)	C4—C9—C10—C19	−178.63 (14)
C10—C1—C2—N3	1.4 (2)	C10—C1—C12—C17	97.0 (2)
C12—C1—C2—N3	−178.77 (14)	C2—C1—C12—C17	−82.8 (2)
O11—C2—N3—C4	176.77 (16)	C10—C1—C12—C13	−81.3 (2)
C1—C2—N3—C4	−3.5 (2)	C2—C1—C12—C13	98.83 (18)
O11—C2—N3—C25	−6.6 (2)	C17—C12—C13—C14	−1.6 (3)
C1—C2—N3—C25	173.12 (15)	C1—C12—C13—C14	176.78 (15)
C2—N3—C4—C5	−175.43 (15)	C12—C13—C14—C15	−0.4 (3)
C25—N3—C4—C5	8.0 (2)	C13—C14—C15—F18	−178.31 (15)
C2—N3—C4—C9	3.8 (2)	C13—C14—C15—C16	2.1 (3)
C25—N3—C4—C9	−172.72 (15)	C14—C15—C16—C17	−1.8 (3)
N3—C4—C5—C6	−178.50 (15)	F18—C15—C16—C17	178.64 (18)
C9—C4—C5—C6	2.3 (3)	C13—C12—C17—C16	1.9 (3)
C4—C5—C6—C7	−0.2 (3)	C1—C12—C17—C16	−176.42 (17)
C5—C6—C7—C8	−1.4 (3)	C15—C16—C17—C12	−0.3 (3)
C6—C7—C8—C9	1.0 (3)	C1—C10—C19—C20	−91.0 (2)
C7—C8—C9—C4	1.0 (2)	C9—C10—C19—C20	87.5 (2)
C7—C8—C9—C10	−178.97 (16)	C1—C10—C19—C24	90.4 (2)
N3—C4—C9—C8	178.12 (14)	C9—C10—C19—C24	−91.09 (19)
C5—C4—C9—C8	−2.6 (2)	C24—C19—C20—C21	−0.1 (3)
N3—C4—C9—C10	−1.9 (2)	C10—C19—C20—C21	−178.68 (16)
C5—C4—C9—C10	177.38 (15)	C19—C20—C21—N22	0.4 (3)
C2—C1—C10—C9	0.4 (2)	C20—C21—N22—C23	−0.7 (3)
C12—C1—C10—C9	−179.50 (15)	C21—N22—C23—C24	0.7 (3)
C2—C1—C10—C19	178.83 (14)	N22—C23—C24—C19	−0.5 (3)
C12—C1—C10—C19	−1.0 (2)	C20—C19—C24—C23	0.1 (2)
C8—C9—C10—C1	179.90 (15)	C10—C19—C24—C23	178.72 (15)
C4—C9—C10—C1	−0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O11^i	0.95	2.58	3.282 (2)	130
C13—H13···N22^ii	0.95	2.60	3.387 (2)	141

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+3/2, z−1/2.