4-[5-(4-Fluoro­phen­yl)-3-isopropyl­isoxazol-4-yl]pyridine

In the title compound, C₁₇H₁₅FN₂O, the exocyclic bond angles at the C atoms of the isoxazole ring bearing the pyridyl and 4-fluoro­phenyl substituents are 129.66 (17) and 134.58 (16)°, respectively. The structure was determined in a study of the mol­ecular geometry of isoxazole derivatives with biological activity as MAPK inhibitors.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.150
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.130
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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-[5-(4-Fluorophenyl)-3-isopropylisoxazol-4-yl]pyridine

Crystal data

C17H15FN2O	F(000) = 1184
Mr = 282.31	Dx = 1.299 Mg m^−3
Monoclinic, C2/c	Melting point: 438 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71069 Å
a = 14.1426 (10) Å	Cell parameters from 3921 reflections
b = 11.8646 (9) Å	θ = 2–28°
c = 17.8516 (13) Å	µ = 0.09 mm^−1
β = 105.475 (4)°	T = 293 K
V = 2886.8 (4) Å^3	Block, colourless
Z = 8	0.53 × 0.41 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer	1995 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.130
Graphite monochromator	θmax = 28.4°, θmin = 2.3°
ω scans	h = −18→18
11215 measured reflections	k = −15→14
3556 independent reflections	l = −23→23

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.076P)^2] where P = (Fo^2 + 2Fc^2)/3
3556 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.27 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
F1	0.65494 (8)	0.47091 (10)	0.22176 (8)	0.0481 (4)
C1	0.46543 (13)	−0.14140 (16)	0.13027 (10)	0.0288 (4)
N2	0.55374 (11)	−0.16047 (13)	0.17470 (10)	0.0356 (4)
O3	0.59749 (8)	−0.05312 (11)	0.19237 (8)	0.0337 (3)
C4	0.53248 (12)	0.02695 (15)	0.15699 (10)	0.0271 (4)
C5	0.44793 (11)	−0.02376 (15)	0.11629 (10)	0.0254 (4)
C6	0.39627 (13)	−0.23637 (16)	0.09777 (11)	0.0336 (4)
H6	0.3302	−0.2121	0.0983	0.039 (5)*
C7	0.41917 (17)	−0.34302 (18)	0.14597 (14)	0.0492 (6)
H7A	0.3736	−0.4011	0.1224	0.071 (5)*
H7B	0.4136	−0.3284	0.1975	0.071 (5)*
H7C	0.4848	−0.3671	0.1485	0.071 (5)*
C8	0.39514 (19)	−0.2571 (2)	0.01311 (13)	0.0549 (6)
H8A	0.3510	−0.3178	−0.0075	0.070 (4)*
H8B	0.4600	−0.2765	0.0102	0.070 (4)*
H8C	0.3738	−0.1900	−0.0167	0.070 (4)*
C9	0.56501 (11)	0.14394 (15)	0.17109 (10)	0.0260 (4)
C10	0.66353 (12)	0.16784 (17)	0.20876 (11)	0.0334 (5)
H10	0.7085	0.1092	0.2227	0.033 (5)*
C11	0.69416 (13)	0.27817 (18)	0.22530 (12)	0.0376 (5)
H11	0.7593	0.2946	0.2502	0.054 (7)*
C12	0.62633 (13)	0.36209 (16)	0.20411 (11)	0.0333 (4)
C13	0.52990 (13)	0.34282 (16)	0.16552 (11)	0.0319 (4)
H13	0.4863	0.4024	0.1504	0.036 (5)*
C14	0.49940 (12)	0.23301 (16)	0.14981 (11)	0.0300 (4)
H14	0.4341	0.2182	0.1246	0.028 (5)*
C15	0.35690 (11)	0.02705 (15)	0.06617 (10)	0.0253 (4)
C16	0.35344 (14)	0.07098 (19)	−0.00605 (11)	0.0403 (5)
H16	0.4093	0.0717	−0.0242	0.081 (9)*
C17	0.26545 (17)	0.1141 (2)	−0.05120 (14)	0.0516 (6)
H17	0.2642	0.1428	−0.0999	0.076 (9)*
N18	0.18295 (13)	0.11676 (18)	−0.02922 (14)	0.0580 (6)
C19	0.18812 (15)	0.0748 (2)	0.04012 (17)	0.0564 (7)
H19	0.1313	0.0760	0.0569	0.073 (8)*
C20	0.27109 (13)	0.02916 (19)	0.08978 (13)	0.0402 (5)
H20	0.2696	0.0005	0.1379	0.034 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0408 (6)	0.0398 (7)	0.0631 (8)	−0.0147 (5)	0.0128 (6)	−0.0147 (6)
C1	0.0259 (8)	0.0320 (10)	0.0261 (9)	0.0021 (7)	0.0030 (7)	0.0022 (8)
N2	0.0287 (8)	0.0321 (9)	0.0392 (10)	−0.0002 (7)	−0.0028 (7)	0.0035 (7)
O3	0.0225 (6)	0.0321 (7)	0.0391 (8)	0.0020 (5)	−0.0048 (5)	0.0047 (6)
C4	0.0191 (7)	0.0340 (10)	0.0253 (9)	0.0031 (7)	0.0008 (6)	0.0043 (8)
C5	0.0216 (8)	0.0287 (10)	0.0241 (9)	0.0014 (7)	0.0029 (6)	0.0021 (8)
C6	0.0294 (9)	0.0329 (11)	0.0349 (11)	−0.0005 (8)	0.0022 (7)	0.0012 (9)
C7	0.0542 (13)	0.0353 (12)	0.0512 (14)	−0.0075 (10)	0.0021 (11)	0.0037 (11)
C8	0.0684 (16)	0.0504 (14)	0.0385 (13)	−0.0125 (12)	0.0016 (11)	−0.0060 (11)
C9	0.0187 (8)	0.0325 (10)	0.0235 (9)	−0.0003 (7)	0.0001 (6)	0.0003 (8)
C10	0.0202 (8)	0.0403 (12)	0.0346 (11)	0.0003 (8)	−0.0016 (7)	0.0025 (9)
C11	0.0214 (9)	0.0476 (13)	0.0389 (11)	−0.0085 (8)	−0.0006 (7)	−0.0047 (10)
C12	0.0317 (9)	0.0328 (11)	0.0352 (11)	−0.0113 (8)	0.0085 (8)	−0.0075 (9)
C13	0.0270 (9)	0.0321 (11)	0.0345 (11)	0.0006 (8)	0.0047 (7)	−0.0014 (8)
C14	0.0186 (8)	0.0357 (11)	0.0314 (10)	−0.0023 (7)	−0.0008 (7)	−0.0032 (8)
C15	0.0189 (8)	0.0240 (9)	0.0283 (10)	−0.0014 (6)	−0.0022 (6)	−0.0029 (8)
C16	0.0361 (10)	0.0470 (13)	0.0328 (11)	0.0100 (9)	0.0007 (8)	0.0049 (10)
C17	0.0537 (14)	0.0494 (14)	0.0384 (13)	0.0126 (11)	−0.0111 (10)	0.0039 (11)
N18	0.0334 (10)	0.0526 (13)	0.0702 (15)	0.0129 (9)	−0.0170 (9)	−0.0057 (11)
C19	0.0232 (10)	0.0585 (16)	0.0816 (19)	0.0077 (10)	0.0038 (10)	0.0009 (15)
C20	0.0251 (9)	0.0471 (13)	0.0489 (13)	0.0024 (8)	0.0108 (8)	0.0013 (10)

Geometric parameters (Å, º)

F1—C12	1.365 (2)	C9—C10	1.405 (2)
C1—N2	1.308 (2)	C10—C11	1.386 (3)
C1—C5	1.428 (3)	C10—H10	0.930
C1—C6	1.503 (3)	C11—C12	1.364 (3)
N2—O3	1.414 (2)	C11—H11	0.930
O3—C4	1.355 (2)	C12—C13	1.373 (3)
C4—C5	1.362 (2)	C13—C14	1.377 (3)
C4—C9	1.463 (3)	C13—H13	0.930
C5—C15	1.485 (2)	C14—H14	0.930
C6—C7	1.516 (3)	C15—C16	1.379 (3)
C6—C8	1.527 (3)	C15—C20	1.387 (2)
C6—H6	0.980	C16—C17	1.387 (3)
C7—H7A	0.960	C16—H16	0.930
C7—H7B	0.960	C17—N18	1.327 (4)
C7—H7C	0.960	C17—H17	0.930
C8—H8A	0.960	N18—C19	1.318 (4)
C8—H8B	0.960	C19—C20	1.379 (3)
C8—H8C	0.960	C19—H19	0.930
C9—C14	1.391 (2)	C20—H20	0.930
N2—C1—C5	111.59 (16)	C11—C10—C9	120.42 (17)
N2—C1—C6	121.46 (16)	C11—C10—H10	119.8
C5—C1—C6	126.92 (16)	C9—C10—H10	119.8
C1—N2—O3	105.64 (14)	C12—C11—C10	118.27 (16)
C4—O3—N2	108.99 (12)	C12—C11—H11	120.9
O3—C4—C5	109.19 (16)	C10—C11—H11	120.9
O3—C4—C9	116.22 (14)	C11—C12—F1	118.90 (16)
C5—C4—C9	134.58 (16)	C11—C12—C13	123.26 (17)
C4—C5—C1	104.60 (15)	F1—C12—C13	117.85 (17)
C4—C5—C15	129.66 (17)	C12—C13—C14	118.35 (17)
C1—C5—C15	125.73 (16)	C12—C13—H13	120.8
C1—C6—C7	112.84 (16)	C14—C13—H13	120.8
C1—C6—C8	109.65 (17)	C13—C14—C9	120.88 (15)
C7—C6—C8	111.83 (19)	C13—C14—H14	119.6
C1—C6—H6	107.4	C9—C14—H14	119.6
C7—C6—H6	107.4	C16—C15—C20	117.48 (16)
C8—C6—H6	107.4	C16—C15—C5	121.68 (15)
C6—C7—H7A	109.5	C20—C15—C5	120.81 (16)
C6—C7—H7B	109.5	C15—C16—C17	119.0 (2)
H7A—C7—H7B	109.5	C15—C16—H16	120.5
C6—C7—H7C	109.5	C17—C16—H16	120.5
H7A—C7—H7C	109.5	N18—C17—C16	124.1 (2)
H7B—C7—H7C	109.5	N18—C17—H17	118.0
C6—C8—H8A	109.5	C16—C17—H17	118.0
C6—C8—H8B	109.5	C19—N18—C17	115.83 (18)
H8A—C8—H8B	109.5	N18—C19—C20	125.2 (2)
C6—C8—H8C	109.5	N18—C19—H19	117.4
H8A—C8—H8C	109.5	C20—C19—H19	117.4
H8B—C8—H8C	109.5	C19—C20—C15	118.4 (2)
C14—C9—C10	118.79 (16)	C19—C20—H20	120.8
C14—C9—C4	121.18 (14)	C15—C20—H20	120.8
C10—C9—C4	120.01 (16)
C5—C1—N2—O3	0.7 (2)	C4—C9—C10—C11	−177.27 (17)
C6—C1—N2—O3	178.67 (15)	C9—C10—C11—C12	0.0 (3)
C1—N2—O3—C4	−0.17 (19)	C10—C11—C12—F1	178.38 (17)
N2—O3—C4—C5	−0.42 (19)	C10—C11—C12—C13	−1.7 (3)
N2—O3—C4—C9	178.27 (14)	C11—C12—C13—C14	2.3 (3)
O3—C4—C5—C1	0.79 (19)	F1—C12—C13—C14	−177.76 (16)
C9—C4—C5—C1	−177.57 (19)	C12—C13—C14—C9	−1.3 (3)
O3—C4—C5—C15	−177.77 (16)	C10—C9—C14—C13	−0.3 (3)
C9—C4—C5—C15	3.9 (3)	C4—C9—C14—C13	177.88 (17)
N2—C1—C5—C4	−0.9 (2)	C4—C5—C15—C16	72.5 (3)
C6—C1—C5—C4	−178.79 (17)	C1—C5—C15—C16	−105.7 (2)
N2—C1—C5—C15	177.70 (16)	C4—C5—C15—C20	−109.2 (2)
C6—C1—C5—C15	−0.2 (3)	C1—C5—C15—C20	72.5 (2)
N2—C1—C6—C7	24.4 (3)	C20—C15—C16—C17	−0.3 (3)
C5—C1—C6—C7	−157.94 (19)	C5—C15—C16—C17	177.96 (19)
N2—C1—C6—C8	−101.0 (2)	C15—C16—C17—N18	0.5 (4)
C5—C1—C6—C8	76.7 (2)	C16—C17—N18—C19	−0.2 (4)
O3—C4—C9—C14	−168.25 (16)	C17—N18—C19—C20	−0.2 (4)
C5—C4—C9—C14	10.0 (3)	N18—C19—C20—C15	0.4 (4)
O3—C4—C9—C10	9.9 (2)	C16—C15—C20—C19	−0.1 (3)
C5—C4—C9—C10	−171.84 (19)	C5—C15—C20—C19	−178.38 (19)
C14—C9—C10—C11	0.9 (3)