organic compounds
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—HO and C—HN hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014638/bh2088sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014638/bh2088IIsup2.hkl |
CCDC reference: 646721
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C)= 0.002 Å
- R factor = 0.049
- wR factor = 0.164
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
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 top
Crystal data top
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) Å3 | Needle, colourless |
Z = 4 | 0.49 × 0.24 × 0.09 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0967P)2 + 0.0759P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O11i | 0.95 | 2.58 | 3.282 (2) | 130 |
C13—H13···N22ii | 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. |