3-(4-Fluoro-3-phenoxy­phen­yl)-5-(4-methoxy­phen­yl)isoxazole

The crystal structure of the title compound, C₂₂H₁₆FNO₃, is stablized by C—H...π inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.067
• wR factor = 0.161
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C22 H16 F N O3

   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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

5-(4-methoxyphenyl)-3-(4-phenoxyphenyl)isoxazole

Crystal data

C22H16FNO3	Z = 2
Mr = 361.36	F(000) = 376
Triclinic, P1	Dx = 1.411 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.787 (4) Å	Cell parameters from 650 reflections
b = 7.559 (5) Å	θ = 1.4–25.1°
c = 19.516 (13) Å	µ = 0.10 mm^−1
α = 87.527 (12)°	T = 290 K
β = 86.000 (12)°	Needle, colourless
γ = 89.946 (12)°	0.29 × 0.05 × 0.02 mm
V = 850.8 (10) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2971 independent reflections
Radiation source: fine-focus sealed tube	1676 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.949, Tmax = 0.999	k = −8→8
8144 measured reflections	l = −23→22

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.101P)^2] where P = (Fo^2 + 2Fc^2)/3
2971 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.20 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	0.2310 (4)	0.0897 (3)	0.18321 (11)	0.0504 (7)
O1	0.6414 (4)	−0.0926 (4)	0.20385 (12)	0.0419 (8)
O2	0.5599 (4)	−0.2863 (4)	0.53108 (14)	0.0486 (8)
O3	0.0424 (5)	−0.4883 (4)	0.82425 (13)	0.0475 (8)
N1	0.5828 (5)	−0.2251 (5)	0.46154 (16)	0.0414 (9)
C1	0.5678 (8)	−0.2496 (6)	0.0064 (2)	0.0495 (12)
C2	0.3911 (7)	−0.2852 (6)	0.0555 (2)	0.0501 (12)
C3	0.4071 (7)	−0.2369 (5)	0.1223 (2)	0.0422 (11)
C4	0.6027 (6)	−0.1481 (5)	0.13860 (19)	0.0323 (10)
C5	0.7820 (7)	−0.1141 (5)	0.0898 (2)	0.0387 (10)
C6	0.7632 (8)	−0.1644 (5)	0.0240 (2)	0.0454 (11)
C7	0.4614 (6)	−0.0865 (5)	0.25390 (18)	0.0311 (10)
C8	0.2590 (7)	0.0056 (5)	0.24480 (19)	0.0327 (10)
C9	0.0878 (6)	0.0164 (5)	0.2963 (2)	0.0366 (10)
C10	0.1229 (6)	−0.0579 (5)	0.3603 (2)	0.0363 (10)
C11	0.3291 (6)	−0.1454 (5)	0.37237 (19)	0.0303 (9)
C12	0.4956 (6)	−0.1608 (5)	0.31785 (18)	0.0315 (10)
C13	0.3696 (6)	−0.2147 (5)	0.44211 (19)	0.0343 (10)
C14	0.3323 (6)	−0.3076 (5)	0.55042 (19)	0.0321 (10)
C15	0.2058 (7)	−0.2628 (5)	0.4965 (2)	0.0335 (10)
C16	0.2703 (6)	−0.3642 (5)	0.62159 (19)	0.0305 (9)
C17	0.4147 (6)	−0.3322 (5)	0.6735 (2)	0.0369 (10)
C18	0.3473 (6)	−0.3745 (5)	0.7416 (2)	0.0367 (10)
C19	0.1319 (7)	−0.4497 (5)	0.75844 (19)	0.0328 (10)
C20	−0.0102 (6)	−0.4903 (5)	0.70720 (19)	0.0375 (10)
C21	0.0575 (6)	−0.4479 (5)	0.63992 (19)	0.0363 (10)
C22	0.1522 (8)	−0.4091 (6)	0.8780 (2)	0.0531 (13)
H1	0.5555	−0.2829	−0.0385	0.059*
H2	0.2586	−0.3427	0.0436	0.060*
H3	0.2885	−0.2636	0.1558	0.051*
H5	0.9153	−0.0573	0.1015	0.046*
H6	0.8837	−0.1408	−0.0092	0.054*
H9	−0.0508	0.0733	0.2881	0.044*
H10	0.0080	−0.0498	0.3958	0.044*
H12	0.6319	−0.2222	0.3249	0.038*
H15	0.053 (6)	−0.265 (4)	0.4960 (17)	0.036 (11)*
H17	0.5594	−0.2814	0.6623	0.044*
H18	0.4462	−0.3525	0.7759	0.044*
H20	−0.1516	−0.5464	0.7184	0.045*
H21	−0.0393	−0.4752	0.6058	0.044*
H22A	0.3002	−0.4637	0.8832	0.080*
H22B	0.0573	−0.4249	0.9202	0.080*
H22C	0.1736	−0.2849	0.8670	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0586 (16)	0.0551 (17)	0.0372 (15)	0.0058 (12)	−0.0088 (12)	0.0085 (12)
O1	0.0300 (15)	0.069 (2)	0.0264 (16)	−0.0062 (14)	0.0040 (13)	−0.0066 (14)
O2	0.0316 (16)	0.077 (2)	0.0368 (18)	0.0028 (14)	−0.0027 (13)	0.0024 (16)
O3	0.0547 (19)	0.060 (2)	0.0276 (17)	−0.0097 (15)	−0.0017 (14)	0.0042 (15)
N1	0.032 (2)	0.067 (3)	0.024 (2)	0.0013 (17)	0.0010 (15)	0.0050 (17)
C1	0.063 (3)	0.054 (3)	0.033 (3)	0.008 (2)	−0.008 (2)	−0.011 (2)
C2	0.044 (3)	0.054 (3)	0.055 (3)	0.000 (2)	−0.014 (2)	−0.019 (2)
C3	0.035 (2)	0.048 (3)	0.043 (3)	−0.002 (2)	0.003 (2)	−0.008 (2)
C4	0.033 (2)	0.037 (3)	0.026 (2)	0.0035 (19)	0.0001 (19)	−0.0016 (19)
C5	0.037 (2)	0.043 (3)	0.035 (3)	−0.006 (2)	0.003 (2)	0.000 (2)
C6	0.054 (3)	0.048 (3)	0.033 (3)	−0.004 (2)	0.006 (2)	−0.002 (2)
C7	0.026 (2)	0.041 (3)	0.026 (2)	−0.0046 (18)	0.0019 (18)	−0.0049 (19)
C8	0.041 (2)	0.031 (2)	0.026 (2)	−0.0018 (19)	−0.008 (2)	0.0038 (19)
C9	0.031 (2)	0.041 (3)	0.039 (3)	0.0053 (19)	−0.007 (2)	−0.004 (2)
C10	0.032 (2)	0.042 (3)	0.035 (3)	0.0017 (19)	0.0044 (19)	−0.006 (2)
C11	0.031 (2)	0.028 (2)	0.032 (2)	−0.0034 (18)	−0.0011 (18)	−0.0031 (18)
C12	0.027 (2)	0.036 (3)	0.032 (2)	0.0026 (17)	−0.0028 (18)	−0.0061 (19)
C13	0.026 (2)	0.046 (3)	0.032 (2)	0.0025 (19)	−0.0015 (19)	−0.002 (2)
C14	0.025 (2)	0.036 (3)	0.036 (3)	0.0004 (18)	−0.0008 (19)	−0.0064 (19)
C15	0.024 (2)	0.044 (3)	0.031 (2)	0.0024 (19)	0.000 (2)	−0.0011 (19)
C16	0.029 (2)	0.030 (2)	0.032 (2)	0.0023 (18)	0.0001 (19)	−0.0030 (18)
C17	0.030 (2)	0.042 (3)	0.039 (3)	0.0007 (19)	−0.002 (2)	−0.003 (2)
C18	0.034 (2)	0.043 (3)	0.034 (3)	−0.002 (2)	−0.010 (2)	−0.003 (2)
C19	0.040 (2)	0.028 (2)	0.030 (2)	0.0033 (19)	−0.005 (2)	0.0018 (18)
C20	0.032 (2)	0.043 (3)	0.037 (3)	−0.0069 (19)	−0.001 (2)	−0.001 (2)
C21	0.034 (2)	0.042 (3)	0.034 (3)	−0.0051 (19)	−0.010 (2)	−0.006 (2)
C22	0.073 (3)	0.058 (3)	0.029 (3)	0.004 (2)	−0.002 (2)	−0.006 (2)

Geometric parameters (Å, º)

F1—C8	1.355 (4)	C13—C15	1.409 (5)
O2—C14	1.352 (4)	C13—C11	1.471 (5)
O2—N1	1.412 (4)	C14—C15	1.354 (5)
O1—C7	1.380 (4)	C15—H15	0.89 (3)
O1—C4	1.391 (4)	C11—C10	1.393 (5)
O3—C19	1.370 (4)	C10—H10	0.9300
O3—C22	1.418 (4)	C20—C21	1.368 (5)
C7—C12	1.373 (5)	C20—H20	0.9300
C7—C8	1.380 (5)	C21—H21	0.9300
C12—C11	1.394 (5)	C4—C5	1.376 (5)
C12—H12	0.9300	C4—C3	1.379 (5)
C9—C8	1.366 (5)	C5—C6	1.366 (5)
C9—C10	1.376 (5)	C5—H5	0.9300
C9—H9	0.9300	C1—C2	1.370 (6)
C19—C20	1.383 (5)	C1—C6	1.373 (6)
C19—C18	1.383 (5)	C1—H1	0.9300
C16—C17	1.386 (5)	C3—C2	1.380 (5)
C16—C21	1.402 (5)	C3—H3	0.9300
C16—C14	1.456 (5)	C22—H22A	0.9600
C17—C18	1.383 (5)	C22—H22B	0.9600
C17—H17	0.9300	C22—H22C	0.9600
C18—H18	0.9300	C6—H6	0.9300
C13—N1	1.317 (4)	C2—H2	0.9300
C14—O2—N1	108.8 (3)	C10—C11—C12	118.7 (4)
C7—O1—C4	120.5 (3)	C10—C11—C13	119.8 (3)
C19—O3—C22	117.0 (3)	C12—C11—C13	121.5 (3)
C12—C7—O1	118.0 (3)	C9—C10—C11	120.5 (4)
C12—C7—C8	118.6 (3)	C9—C10—H10	119.7
O1—C7—C8	123.1 (3)	C11—C10—H10	119.7
C7—C12—C11	120.9 (3)	C21—C20—C19	119.9 (4)
C7—C12—H12	119.5	C21—C20—H20	120.0
C11—C12—H12	119.5	C19—C20—H20	120.0
C8—C9—C10	119.2 (4)	C20—C21—C16	121.1 (3)
C8—C9—H9	120.4	C20—C21—H21	119.4
C10—C9—H9	120.4	C16—C21—H21	119.4
O3—C19—C20	115.3 (3)	C5—C4—C3	120.7 (4)
O3—C19—C18	124.5 (3)	C5—C4—O1	114.7 (3)
C20—C19—C18	120.1 (4)	C3—C4—O1	124.6 (3)
C17—C16—C21	117.9 (4)	C6—C5—C4	119.6 (4)
C17—C16—C14	121.5 (3)	C6—C5—H5	120.2
C21—C16—C14	120.5 (3)	C4—C5—H5	120.2
C18—C17—C16	121.2 (4)	C2—C1—C6	119.6 (4)
C18—C17—H17	119.4	C2—C1—H1	120.2
C16—C17—H17	119.4	C6—C1—H1	120.2
C17—C18—C19	119.5 (3)	C4—C3—C2	118.7 (4)
C17—C18—H18	120.2	C4—C3—H3	120.7
C19—C18—H18	120.2	C2—C3—H3	120.7
F1—C8—C9	119.1 (3)	O3—C22—H22A	109.5
F1—C8—C7	118.9 (3)	O3—C22—H22B	109.5
C9—C8—C7	122.0 (3)	H22A—C22—H22B	109.5
N1—C13—C15	111.5 (3)	O3—C22—H22C	109.5
N1—C13—C11	119.6 (3)	H22A—C22—H22C	109.5
C15—C13—C11	128.7 (3)	H22B—C22—H22C	109.5
O2—C14—C15	109.2 (3)	C5—C6—C1	120.6 (4)
O2—C14—C16	117.6 (3)	C5—C6—H6	119.7
C15—C14—C16	133.1 (3)	C1—C6—H6	119.7
C14—C15—C13	105.2 (3)	C1—C2—C3	120.8 (4)
C14—C15—H15	127 (2)	C1—C2—H2	119.6
C13—C15—H15	128 (2)	C3—C2—H2	119.6
C13—N1—O2	105.2 (3)
C4—O1—C7—C12	132.0 (4)	C15—C13—N1—O2	1.4 (4)
C4—O1—C7—C8	−54.7 (5)	C11—C13—N1—O2	176.8 (3)
O1—C7—C12—C11	174.2 (3)	C14—O2—N1—C13	−0.8 (4)
C8—C7—C12—C11	0.6 (5)	C7—C12—C11—C10	2.1 (5)
C22—O3—C19—C20	−164.2 (3)	C7—C12—C11—C13	−176.2 (4)
C22—O3—C19—C18	15.4 (5)	N1—C13—C11—C10	−150.3 (4)
C21—C16—C17—C18	−2.7 (6)	C15—C13—C11—C10	24.2 (6)
C14—C16—C17—C18	175.2 (4)	N1—C13—C11—C12	28.0 (6)
C16—C17—C18—C19	−0.2 (6)	C15—C13—C11—C12	−157.5 (4)
O3—C19—C18—C17	−176.4 (3)	C8—C9—C10—C11	−0.9 (6)
C20—C19—C18—C17	3.2 (6)	C12—C11—C10—C9	−2.0 (6)
C10—C9—C8—F1	−175.3 (3)	C13—C11—C10—C9	176.3 (4)
C10—C9—C8—C7	3.8 (6)	O3—C19—C20—C21	176.4 (3)
C12—C7—C8—F1	175.4 (3)	C18—C19—C20—C21	−3.3 (6)
O1—C7—C8—F1	2.2 (5)	C19—C20—C21—C16	0.3 (6)
C12—C7—C8—C9	−3.6 (6)	C17—C16—C21—C20	2.7 (6)
O1—C7—C8—C9	−176.9 (3)	C14—C16—C21—C20	−175.2 (4)
N1—O2—C14—C15	0.0 (4)	C7—O1—C4—C5	167.2 (3)
N1—O2—C14—C16	−177.8 (3)	C7—O1—C4—C3	−15.3 (6)
C17—C16—C14—O2	24.9 (5)	C3—C4—C5—C6	1.9 (6)
C21—C16—C14—O2	−157.3 (3)	O1—C4—C5—C6	179.5 (3)
C17—C16—C14—C15	−152.3 (4)	C5—C4—C3—C2	−2.4 (6)
C21—C16—C14—C15	25.6 (7)	O1—C4—C3—C2	−179.7 (4)
O2—C14—C15—C13	0.8 (4)	C4—C5—C6—C1	−0.5 (6)
C16—C14—C15—C13	178.1 (4)	C2—C1—C6—C5	−0.4 (7)
N1—C13—C15—C14	−1.4 (5)	C6—C1—C2—C3	−0.1 (7)
C11—C13—C15—C14	−176.3 (4)	C4—C3—C2—C1	1.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg2^i	0.93	2.73	3.423 (5)	132
C22—H22A···Cg1^ii	0.96	2.75	3.452 (5)	131

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