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The mol­ecular structure of the title compound, C17H15FN2O, was determined in the course of our studies on mitogen-activated protein kinase inhibitors. The exocyclic bond angles at the carbon atoms of the isoxazole ring bearing the pyridyl and 4-fluoro­phenyl rings are 130.0 (2) and 129.2 (2)°, respectively. The pyridine and 4-fluoro­phenyl rings are twisted relative to the isoxazole ring by 80.2 (2) and 19.1 (1)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030467/cf2051sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030467/cf2051Isup2.hkl
Contains datablock I

CCDC reference: 620728

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.066
  • wR factor = 0.198
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger et al., 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-[3-(4-fluorophenyl)-5-isopropylisoxazol-4-yl]pyridine top
Crystal data top
C17H15FN2OF(000) = 1184
Mr = 282.31Dx = 1.267 Mg m3
Monoclinic, C2/cMelting point: 147 K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54178 Å
a = 15.490 (2) ÅCell parameters from 25 reflections
b = 11.4393 (9) Åθ = 35–46°
c = 17.878 (3) ŵ = 0.73 mm1
β = 110.838 (7)°T = 298 K
V = 2960.7 (7) Å3Needle, colourless
Z = 80.51 × 0.16 × 0.16 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.017
Radiation source: rotating anodeθmax = 69.9°, θmin = 4.9°
Graphite monochromatorh = 1718
ω/2θ scansk = 013
2894 measured reflectionsl = 210
2797 independent reflections3 standard reflections every 60 min
2167 reflections with I > 2σ(I) intensity decay: 5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.198 w = 1/[σ2(Fo2) + (0.1116P)2 + 1.374P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2797 reflectionsΔρmax = 0.41 e Å3
209 parametersΔρmin = 0.24 e Å3
28 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0047 (5)
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.64349 (14)0.49466 (15)0.70057 (13)0.1036 (7)
C10.46754 (18)0.1426 (2)0.62498 (16)0.0720 (7)
O20.55423 (13)0.16164 (16)0.67730 (12)0.0821 (6)
N30.59757 (14)0.0535 (2)0.70073 (13)0.0705 (6)
C40.53745 (14)0.0261 (2)0.66258 (12)0.0543 (5)
C50.45255 (15)0.0273 (2)0.61368 (13)0.0562 (6)
C60.4111 (3)0.2478 (3)0.5896 (2)0.0982 (10)
H6A0.35110.21980.55320.118*0.80
H6B0.45280.31190.61590.118*0.20
C70.3924 (4)0.3264 (4)0.6502 (3)0.1188 (16)0.80
H7A0.38610.27970.69250.178*0.80
H7B0.44290.38000.67190.178*0.80
H7C0.33640.36940.62450.178*0.80
C80.4547 (4)0.3176 (5)0.5390 (3)0.1223 (17)0.80
H8A0.48360.26490.51330.184*0.80
H8B0.40770.36150.49910.184*0.80
H8C0.50020.37030.57290.184*0.80
C7A0.3288 (11)0.269 (2)0.6152 (14)0.120 (7)0.20
H7D0.29450.33550.58660.181*0.20
H7E0.28980.20170.60350.181*0.20
H7F0.35020.28490.67160.181*0.20
C8A0.3965 (15)0.2677 (19)0.5017 (5)0.107 (6)0.20
H8A10.35710.33430.48230.160*0.20
H8A20.45500.28160.49610.160*0.20
H8A30.36820.19980.47130.160*0.20
C90.56412 (14)0.1502 (2)0.67220 (12)0.0537 (6)
C100.65736 (16)0.1809 (2)0.70143 (15)0.0671 (7)
H100.70220.12260.71430.081*
C110.68389 (18)0.2965 (3)0.71141 (17)0.0755 (8)
H110.74610.31680.73150.091*
C120.61739 (19)0.3807 (2)0.69141 (16)0.0717 (7)
C130.52525 (17)0.3544 (2)0.66216 (15)0.0672 (7)
H130.48120.41350.64890.081*
C140.49902 (15)0.2388 (2)0.65276 (14)0.0607 (6)
H140.43650.21990.63300.073*
C150.36566 (14)0.0269 (2)0.55966 (13)0.0557 (6)
C160.35634 (19)0.0630 (3)0.48367 (15)0.0772 (8)
H160.40560.05680.46570.093*
C170.2736 (2)0.1083 (3)0.43503 (19)0.0975 (10)
H170.26880.13260.38410.117*
N180.20007 (17)0.1199 (3)0.4556 (2)0.0998 (9)
C190.21053 (19)0.0859 (3)0.5291 (3)0.0956 (11)
H190.16040.09440.54560.115*
C200.29021 (17)0.0388 (3)0.58263 (18)0.0741 (7)
H200.29310.01560.63330.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0916 (12)0.0774 (12)0.1318 (16)0.0281 (9)0.0276 (11)0.0231 (10)
C10.0634 (14)0.0680 (16)0.0779 (16)0.0005 (12)0.0168 (12)0.0053 (13)
O20.0740 (12)0.0654 (11)0.0928 (13)0.0097 (9)0.0123 (10)0.0129 (9)
N30.0567 (11)0.0715 (14)0.0716 (13)0.0082 (10)0.0086 (9)0.0102 (10)
C40.0456 (11)0.0657 (13)0.0489 (11)0.0038 (9)0.0132 (9)0.0025 (9)
C50.0502 (12)0.0607 (13)0.0564 (12)0.0019 (9)0.0173 (9)0.0003 (10)
C60.099 (2)0.0650 (18)0.120 (3)0.0119 (16)0.026 (2)0.0039 (17)
C70.141 (4)0.102 (3)0.136 (3)0.043 (3)0.076 (3)0.031 (3)
C80.150 (4)0.117 (3)0.114 (3)0.033 (3)0.064 (3)0.030 (3)
C7A0.119 (8)0.114 (8)0.122 (8)0.006 (5)0.036 (5)0.003 (5)
C8A0.110 (7)0.099 (7)0.105 (7)0.006 (5)0.032 (5)0.009 (5)
C90.0421 (10)0.0689 (14)0.0451 (10)0.0006 (9)0.0094 (8)0.0008 (9)
C100.0457 (12)0.0791 (16)0.0690 (15)0.0014 (11)0.0110 (10)0.0026 (12)
C110.0500 (13)0.0895 (19)0.0775 (16)0.0139 (13)0.0110 (11)0.0106 (14)
C120.0702 (15)0.0697 (16)0.0690 (15)0.0170 (12)0.0172 (12)0.0130 (12)
C130.0596 (14)0.0643 (14)0.0711 (15)0.0003 (11)0.0153 (11)0.0068 (11)
C140.0445 (11)0.0674 (14)0.0631 (13)0.0026 (10)0.0105 (9)0.0070 (11)
C150.0437 (10)0.0567 (12)0.0603 (12)0.0048 (9)0.0108 (9)0.0068 (10)
C160.0643 (15)0.100 (2)0.0616 (14)0.0096 (14)0.0158 (11)0.0059 (14)
C170.084 (2)0.115 (3)0.0690 (17)0.0156 (19)0.0022 (15)0.0073 (17)
N180.0602 (14)0.098 (2)0.111 (2)0.0097 (13)0.0070 (14)0.0051 (17)
C190.0486 (14)0.092 (2)0.139 (3)0.0014 (14)0.0253 (17)0.013 (2)
C200.0553 (13)0.0784 (17)0.0884 (18)0.0005 (12)0.0254 (12)0.0029 (14)
Geometric parameters (Å, º) top
F1—C121.357 (3)C8A—H8A10.960
C1—C51.342 (4)C8A—H8A20.960
C1—O21.354 (3)C8A—H8A30.960
C1—C61.490 (4)C9—C141.384 (3)
O2—N31.399 (3)C9—C101.395 (3)
N3—C41.307 (3)C10—C111.378 (4)
C4—C51.431 (3)C10—H100.930
C4—C91.472 (3)C11—C121.362 (4)
C5—C151.485 (3)C11—H110.930
C6—C71.512 (4)C12—C131.367 (4)
C6—C7A1.520 (5)C13—C141.376 (3)
C6—C8A1.523 (5)C13—H130.930
C6—C81.532 (4)C14—H140.930
C6—H6A0.980C15—C201.376 (3)
C6—H6B0.980C15—C161.378 (4)
C7—H7A0.960C16—C171.369 (4)
C7—H7B0.960C16—H160.930
C7—H7C0.960C17—N181.321 (5)
C8—H8A0.960C17—H170.930
C8—H8B0.960N18—C191.324 (5)
C8—H8C0.960C19—C201.374 (4)
C7A—H7D0.960C19—H190.930
C7A—H7E0.960C20—H200.930
C7A—H7F0.960
C5—C1—O2109.8 (2)H7E—C7A—H7F109.5
C5—C1—C6133.3 (3)C6—C8A—H8A1109.5
O2—C1—C6116.9 (3)C6—C8A—H8A2109.5
C1—O2—N3108.50 (19)H8A1—C8A—H8A2109.5
C4—N3—O2106.41 (18)C6—C8A—H8A3109.5
N3—C4—C5110.5 (2)H8A1—C8A—H8A3109.5
N3—C4—C9119.5 (2)H8A2—C8A—H8A3109.5
C5—C4—C9129.9 (2)C14—C9—C10118.3 (2)
C1—C5—C4104.8 (2)C14—C9—C4121.89 (19)
C1—C5—C15125.2 (2)C10—C9—C4119.8 (2)
C4—C5—C15130.0 (2)C11—C10—C9120.8 (2)
C1—C6—C7114.1 (3)C11—C10—H10119.6
C1—C6—C7A115.6 (9)C9—C10—H10119.6
C7—C6—C7A45.0 (9)C12—C11—C10118.8 (2)
C1—C6—C8A114.1 (8)C12—C11—H11120.6
C7A—C6—C8A117.0 (13)C10—C11—H11120.6
C1—C6—C8110.9 (3)F1—C12—C11118.8 (2)
C7—C6—C8110.5 (4)F1—C12—C13118.9 (3)
C1—C6—H6A107.0C11—C12—C13122.3 (3)
C7—C6—H6A107.0C12—C13—C14118.7 (2)
C8—C6—H6A107.0C12—C13—H13120.6
C1—C6—H6B102.3C14—C13—H13120.6
C7A—C6—H6B102.3C13—C14—C9121.1 (2)
C8A—C6—H6B102.3C13—C14—H14119.5
C6—C7—H7A109.5C9—C14—H14119.5
C6—C7—H7B109.5C20—C15—C16117.5 (2)
H7A—C7—H7B109.5C20—C15—C5121.1 (2)
C6—C7—H7C109.5C16—C15—C5121.3 (2)
H7A—C7—H7C109.5C17—C16—C15119.1 (3)
H7B—C7—H7C109.5C17—C16—H16120.5
C6—C8—H8A109.5C15—C16—H16120.5
C6—C8—H8B109.5N18—C17—C16124.5 (3)
H8A—C8—H8B109.5N18—C17—H17117.8
C6—C8—H8C109.5C16—C17—H17117.8
H8A—C8—H8C109.5C17—N18—C19115.7 (3)
H8B—C8—H8C109.5N18—C19—C20124.7 (3)
C6—C7A—H7D109.5N18—C19—H19117.7
C6—C7A—H7E109.5C20—C19—H19117.7
H7D—C7A—H7E109.5C19—C20—C15118.6 (3)
C6—C7A—H7F109.5C19—C20—H20120.7
H7D—C7A—H7F109.5C15—C20—H20120.7
C5—C1—O2—N30.3 (3)C5—C4—C9—C10159.0 (2)
C6—C1—O2—N3177.1 (2)C14—C9—C10—C110.6 (4)
C1—O2—N3—C40.3 (3)C4—C9—C10—C11179.6 (2)
O2—N3—C4—C50.6 (3)C9—C10—C11—C120.7 (4)
O2—N3—C4—C9177.44 (19)C10—C11—C12—F1179.4 (2)
O2—C1—C5—C40.6 (3)C10—C11—C12—C130.3 (4)
C6—C1—C5—C4176.1 (3)F1—C12—C13—C14179.8 (2)
O2—C1—C5—C15179.3 (2)C11—C12—C13—C140.1 (4)
C6—C1—C5—C152.6 (5)C12—C13—C14—C90.1 (4)
N3—C4—C5—C10.8 (3)C10—C9—C14—C130.2 (4)
C9—C4—C5—C1177.0 (2)C4—C9—C14—C13180.0 (2)
N3—C4—C5—C15179.4 (2)C1—C5—C15—C2079.7 (3)
C9—C4—C5—C151.6 (4)C4—C5—C15—C20102.0 (3)
C5—C1—C6—C7121.2 (4)C1—C5—C15—C1697.9 (3)
O2—C1—C6—C762.2 (4)C4—C5—C15—C1680.5 (3)
C5—C1—C6—C7A71.4 (11)C20—C15—C16—C170.2 (4)
O2—C1—C6—C7A112.1 (11)C5—C15—C16—C17177.5 (3)
C5—C1—C6—C8A68.6 (10)C15—C16—C17—N180.3 (5)
O2—C1—C6—C8A108.0 (10)C16—C17—N18—C191.0 (6)
C5—C1—C6—C8113.2 (4)C17—N18—C19—C201.3 (5)
O2—C1—C6—C863.3 (4)N18—C19—C20—C150.8 (5)
N3—C4—C9—C14161.5 (2)C16—C15—C20—C190.1 (4)
C5—C4—C9—C1420.8 (4)C5—C15—C20—C19177.7 (3)
N3—C4—C9—C1018.7 (3)
 

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