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The title compound, C21H16FNO2, is chiral, having an asymmetric C atom, and is found to crystallize in a non-centrosymmetric space group. The five-membered isoxazole ring exists in an envelope conformation. The crystal structure is stabilized by weak inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030807/xu2093sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030807/xu2093Isup2.hkl
Contains datablock I

CCDC reference: 621547

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.081
  • wR factor = 0.207
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O1
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H16 F N O2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 1873 Count of symmetry unique reflns 1912 Completeness (_total/calc) 97.96% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT792_ALERT_1_G Check the Absolute Configuration of C13 = ... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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-Fluoro-3-phenoxyphenyl)-3-phenyl-4,5-dihydroisoxazole top
Crystal data top
C21H16FNO2F(000) = 696
Mr = 333.35Dx = 1.308 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 375 reflections
a = 33.31 (2) Åθ = 1.6–25.4°
b = 8.840 (6) ŵ = 0.09 mm1
c = 5.749 (4) ÅT = 290 K
V = 1693.0 (19) Å3Block, colorless
Z = 40.43 × 0.12 × 0.03 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1873 independent reflections
Radiation source: fine-focus sealed tube1486 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
φ and ω scansθmax = 26.4°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 4038
Tmin = 0.948, Tmax = 0.998k = 1110
12350 measured reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.207H-atom parameters constrained
S = 1.32 w = 1/[σ2(Fo2) + (0.1004P)2 + 0.0067P]
where P = (Fo2 + 2Fc2)/3
1873 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.20 e Å3
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*/Ueq
N10.21744 (14)0.3229 (5)0.1483 (11)0.0748 (15)
O10.39796 (11)0.0930 (6)0.3563 (8)0.0946 (16)
O20.25547 (11)0.3898 (5)0.1029 (11)0.0962 (18)
F10.40133 (10)0.0630 (4)0.0575 (9)0.1020 (15)
C10.51367 (19)0.2600 (7)0.3257 (14)0.0839 (19)
C20.50103 (19)0.1711 (7)0.5038 (12)0.0795 (18)
C30.46230 (16)0.1144 (7)0.5113 (11)0.0689 (16)
C40.43656 (14)0.1511 (6)0.3299 (11)0.0611 (14)
C50.44865 (17)0.2408 (6)0.1475 (11)0.0669 (16)
C60.48748 (18)0.2955 (6)0.1467 (12)0.0739 (17)
C70.36965 (16)0.1158 (7)0.1828 (10)0.0656 (17)
C80.37054 (16)0.0348 (7)0.0200 (12)0.0667 (16)
C90.34132 (16)0.0483 (6)0.1875 (13)0.0680 (16)
C100.30948 (15)0.1446 (6)0.1464 (11)0.0615 (15)
C110.30764 (15)0.2287 (5)0.0580 (11)0.0545 (13)
C120.33806 (16)0.2160 (6)0.2237 (10)0.0604 (14)
C130.27204 (16)0.3283 (5)0.1133 (12)0.0659 (16)
C140.20720 (14)0.2434 (5)0.0278 (10)0.0516 (13)
C150.23666 (15)0.2457 (6)0.2274 (11)0.0604 (14)
C160.16870 (14)0.1634 (5)0.0301 (10)0.0500 (12)
C170.14057 (19)0.1830 (7)0.1456 (13)0.0795 (18)
C180.10428 (19)0.1089 (9)0.1363 (17)0.097 (2)
C190.09522 (18)0.0155 (7)0.0457 (16)0.085 (2)
C200.12230 (16)0.0050 (8)0.2180 (15)0.085 (2)
C210.15879 (16)0.0701 (6)0.2146 (12)0.0703 (17)
H10.53980.29690.32390.101*
H20.51880.14770.62340.095*
H30.45380.05370.63390.083*
H50.43100.26410.02720.080*
H60.49610.35670.02500.089*
H90.34300.00620.32550.082*
H100.28910.15340.25610.074*
H120.33730.27350.35920.072*
H130.28070.41170.21380.079*
H15A0.22620.30130.35970.073*
H15B0.24400.14430.27590.073*
H170.14630.24650.27020.095*
H180.08570.12250.25520.116*
H190.07060.03370.05100.102*
H200.11640.07030.34020.102*
H210.17670.05770.33700.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.058 (3)0.074 (3)0.092 (4)0.006 (2)0.006 (3)0.039 (3)
O10.055 (2)0.159 (4)0.070 (3)0.007 (2)0.003 (2)0.057 (3)
O20.066 (2)0.082 (3)0.140 (5)0.002 (2)0.003 (3)0.065 (3)
F10.076 (2)0.102 (3)0.128 (4)0.0248 (19)0.039 (2)0.026 (3)
C10.058 (4)0.112 (5)0.082 (5)0.004 (3)0.008 (4)0.002 (4)
C20.062 (4)0.113 (5)0.063 (4)0.014 (3)0.015 (3)0.007 (4)
C30.065 (3)0.086 (4)0.056 (4)0.020 (3)0.002 (3)0.015 (3)
C40.045 (3)0.081 (3)0.057 (3)0.017 (2)0.008 (3)0.008 (3)
C50.055 (3)0.082 (4)0.063 (4)0.017 (3)0.000 (3)0.021 (3)
C60.064 (4)0.087 (4)0.071 (4)0.003 (3)0.005 (3)0.011 (4)
C70.051 (3)0.095 (4)0.051 (4)0.007 (3)0.004 (3)0.035 (3)
C80.052 (3)0.074 (3)0.073 (5)0.006 (3)0.017 (3)0.018 (3)
C90.069 (3)0.061 (3)0.074 (4)0.018 (3)0.015 (4)0.001 (3)
C100.052 (3)0.070 (3)0.063 (4)0.019 (3)0.003 (3)0.008 (3)
C110.052 (3)0.047 (2)0.064 (4)0.013 (2)0.001 (3)0.012 (3)
C120.053 (3)0.072 (3)0.056 (4)0.009 (3)0.005 (3)0.008 (3)
C130.058 (3)0.048 (2)0.091 (5)0.001 (2)0.004 (3)0.011 (3)
C140.055 (3)0.043 (2)0.057 (3)0.013 (2)0.009 (3)0.015 (3)
C150.052 (3)0.062 (3)0.067 (4)0.005 (2)0.001 (3)0.009 (3)
C160.047 (3)0.048 (2)0.055 (3)0.011 (2)0.005 (3)0.001 (3)
C170.081 (4)0.091 (4)0.067 (4)0.001 (3)0.015 (4)0.016 (4)
C180.066 (4)0.118 (5)0.106 (6)0.002 (4)0.029 (4)0.010 (6)
C190.057 (4)0.084 (4)0.114 (7)0.004 (3)0.006 (4)0.018 (5)
C200.057 (3)0.093 (4)0.104 (6)0.009 (3)0.015 (4)0.029 (4)
C210.057 (3)0.080 (4)0.074 (4)0.000 (3)0.001 (3)0.029 (3)
Geometric parameters (Å, º) top
N1—C141.279 (7)C3—H30.9300
N1—O21.422 (6)C5—C61.381 (8)
C16—C211.384 (8)C5—H50.9300
C16—C171.389 (8)C10—C91.380 (7)
C16—C141.464 (7)C10—C111.392 (8)
O1—C71.387 (7)C10—H100.9300
O1—C41.393 (6)C9—C81.375 (9)
C15—C141.510 (8)C9—H90.9300
C15—C131.534 (8)C17—C181.376 (9)
C15—H15A0.9700C17—H170.9300
C15—H15B0.9700C11—C131.511 (7)
C12—C71.396 (8)C20—C191.352 (10)
C12—C111.395 (8)C20—H200.9300
C12—H120.9300C2—C11.358 (10)
C21—C201.385 (8)C2—H20.9300
C21—H210.9300C13—H130.9800
F1—C81.359 (6)C1—C61.385 (10)
C7—C81.368 (9)C1—H10.9300
O2—C131.465 (8)C19—C181.367 (11)
C4—C51.375 (8)C19—H190.9300
C4—C31.389 (8)C18—H180.9300
C3—C21.385 (8)C6—H60.9300
C14—N1—O2108.7 (5)C8—C9—C10118.5 (7)
C21—C16—C17118.1 (5)C8—C9—H9120.7
C21—C16—C14120.3 (5)C10—C9—H9120.7
C17—C16—C14121.6 (5)C18—C17—C16120.4 (7)
C7—O1—C4119.7 (4)C18—C17—H17119.8
C14—C15—C13100.4 (5)C16—C17—H17119.8
C14—C15—H15A111.7C10—C11—C12120.1 (5)
C13—C15—H15A111.7C10—C11—C13121.6 (5)
C14—C15—H15B111.7C12—C11—C13118.2 (6)
C13—C15—H15B111.7C19—C20—C21120.7 (7)
H15A—C15—H15B109.5C19—C20—H20119.6
C7—C12—C11118.9 (6)C21—C20—H20119.6
C7—C12—H12120.5C1—C2—C3121.4 (6)
C11—C12—H12120.5C1—C2—H2119.3
C16—C21—C20120.4 (6)C3—C2—H2119.3
C16—C21—H21119.8F1—C8—C7119.0 (6)
C20—C21—H21119.8F1—C8—C9118.6 (6)
N1—C14—C16120.4 (5)C7—C8—C9122.4 (5)
N1—C14—C15114.9 (4)O2—C13—C11109.5 (5)
C16—C14—C15124.7 (4)O2—C13—C15104.5 (4)
C8—C7—O1121.4 (6)C11—C13—C15114.6 (4)
C8—C7—C12119.5 (5)O2—C13—H13109.4
O1—C7—C12118.9 (6)C11—C13—H13109.4
N1—O2—C13109.7 (4)C15—C13—H13109.4
C5—C4—C3121.8 (5)C2—C1—C6119.8 (6)
C5—C4—O1124.5 (5)C2—C1—H1120.1
C3—C4—O1113.7 (5)C6—C1—H1120.1
C2—C3—C4117.9 (6)C20—C19—C18119.6 (6)
C2—C3—H3121.1C20—C19—H19120.2
C4—C3—H3121.1C18—C19—H19120.2
C4—C5—C6118.6 (6)C19—C18—C17120.8 (7)
C4—C5—H5120.7C19—C18—H18119.6
C6—C5—H5120.7C17—C18—H18119.6
C9—C10—C11120.5 (6)C5—C6—C1120.5 (6)
C9—C10—H10119.7C5—C6—H6119.7
C11—C10—H10119.7C1—C6—H6119.7
C17—C16—C21—C202.1 (8)C9—C10—C11—C13176.6 (5)
C14—C16—C21—C20179.6 (5)C7—C12—C11—C101.3 (7)
O2—N1—C14—C16178.9 (4)C7—C12—C11—C13175.2 (4)
O2—N1—C14—C151.2 (6)C16—C21—C20—C192.3 (10)
C21—C16—C14—N1176.0 (5)C4—C3—C2—C10.1 (10)
C17—C16—C14—N16.6 (7)O1—C7—C8—F14.2 (7)
C21—C16—C14—C156.6 (7)C12—C7—C8—F1179.7 (5)
C17—C16—C14—C15170.8 (5)O1—C7—C8—C9175.6 (5)
C13—C15—C14—N18.9 (6)C12—C7—C8—C90.1 (8)
C13—C15—C14—C16173.5 (4)C10—C9—C8—F1178.2 (4)
C4—O1—C7—C876.1 (7)C10—C9—C8—C71.6 (8)
C4—O1—C7—C12108.4 (6)N1—O2—C13—C11110.1 (5)
C11—C12—C7—C81.4 (7)N1—O2—C13—C1513.0 (6)
C11—C12—C7—O1174.3 (4)C10—C11—C13—O232.7 (6)
C14—N1—O2—C137.8 (6)C12—C11—C13—O2150.8 (4)
C7—O1—C4—C54.7 (9)C10—C11—C13—C1584.3 (7)
C7—O1—C4—C3177.3 (6)C12—C11—C13—C1592.2 (6)
C5—C4—C3—C20.0 (9)C14—C15—C13—O212.4 (5)
O1—C4—C3—C2178.1 (5)C14—C15—C13—C11107.4 (6)
C3—C4—C5—C60.2 (9)C3—C2—C1—C60.0 (11)
O1—C4—C5—C6177.7 (6)C21—C20—C19—C181.4 (11)
C11—C10—C9—C81.5 (7)C20—C19—C18—C170.4 (12)
C21—C16—C17—C181.1 (9)C16—C17—C18—C190.2 (11)
C14—C16—C17—C18178.6 (6)C4—C5—C6—C10.3 (9)
C9—C10—C11—C120.1 (7)C2—C1—C6—C50.2 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···O2i0.972.363.305 (7)166
Symmetry code: (i) x+1/2, y1/2, z1/2.
 

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