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The title compound, C15H12NO2F3, adopts the phenol–imine tautomeric form. The two aromatic rings are twisted with respect to each other, with a dihedral angle of 17.83 (19)°. O—H...N and O—H...F intra­molecular inter­actions are found in the mol­ecule, and the solid-state structure is stabilized by inter­molecular C—H...O and C—H...F hydrogen bonds, to form a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010342/sj6066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010342/sj6066Isup2.hkl
Contains datablock I

CCDC reference: 272112

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.054
  • wR factor = 0.123
  • Data-to-parameter ratio = 8.0

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 0.142 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.97 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. F2 .. 2.57 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. F3 .. 2.79 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. F1 .. 2.77 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. F3 .. 2.90 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15B .. O1 .. 2.88 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C11 .. F3 .. 3.75 Ang.
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 26.00 From the CIF: _reflns_number_total 1562 Count of symmetry unique reflns 1562 Completeness (_total/calc) 100.00% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1998).

(E)-2-methoxy-6-[(2-trifluoromethylphenylimino)methyl]phenol top
Crystal data top
C15H12F3NO2Dx = 1.471 Mg m3
Mr = 295.26Melting point = 390–392 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3996 reflections
a = 5.2070 (5) Åθ = 1.8–25.5°
b = 14.0918 (18) ŵ = 0.13 mm1
c = 18.1737 (18) ÅT = 296 K
V = 1333.5 (3) Å3Needle, orange
Z = 40.50 × 0.29 × 0.18 mm
F(000) = 608
Data collection top
Stoe IPDS 2
diffractometer
1562 independent reflections
Radiation source: fine-focus sealed tube931 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.142
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.8°
rotation method scansh = 66
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1716
Tmin = 0.954, Tmax = 0.979l = 2222
8826 measured reflections
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)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0641P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
1562 reflectionsΔρmax = 0.22 e Å3
196 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.015 (3)
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
C11.1258 (8)0.6089 (3)0.3399 (2)0.0622 (10)
H11.11000.54720.32220.075*
C21.3066 (8)0.6298 (3)0.3915 (2)0.0639 (10)
H21.41410.58220.40910.077*
C31.3314 (9)0.7218 (3)0.4180 (2)0.0648 (10)
H31.45650.73540.45300.078*
C41.1738 (8)0.7927 (3)0.3932 (2)0.0578 (9)
C50.9830 (8)0.7721 (3)0.34060 (19)0.0532 (9)
C60.9622 (8)0.6812 (3)0.3134 (2)0.0554 (9)
C70.7752 (8)0.6570 (3)0.25699 (19)0.0562 (10)
H70.76830.59500.23970.067*
C80.4371 (7)0.6914 (3)0.17692 (19)0.0542 (9)
C90.3588 (9)0.6000 (3)0.1642 (2)0.0648 (10)
H90.43340.55060.19060.078*
C100.1712 (9)0.5800 (3)0.1128 (2)0.0746 (12)
H100.12020.51750.10520.090*
C110.0597 (10)0.6513 (4)0.0731 (2)0.0755 (13)
H110.06600.63740.03840.091*
C120.1339 (9)0.7435 (3)0.0846 (2)0.0680 (12)
H120.05850.79180.05730.082*
C130.3206 (8)0.7657 (3)0.13666 (18)0.0558 (9)
C140.3941 (9)0.8650 (3)0.1486 (2)0.0653 (11)
C151.3758 (9)0.9100 (3)0.4673 (2)0.0781 (13)
H15A1.36770.97690.47720.117*
H15B1.54050.89460.44680.117*
H15C1.35160.87550.51230.117*
F10.6403 (6)0.88242 (19)0.13631 (16)0.0887 (9)
F20.3478 (7)0.89582 (17)0.21757 (14)0.0927 (9)
F30.2631 (6)0.92538 (17)0.10533 (15)0.0918 (9)
N10.6211 (7)0.7180 (2)0.23062 (15)0.0560 (8)
O10.8323 (6)0.8441 (2)0.31810 (15)0.0702 (8)
O21.1794 (6)0.88493 (19)0.41644 (16)0.0765 (9)
H1A0.710 (10)0.809 (3)0.286 (2)0.090 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.066 (2)0.053 (2)0.068 (2)0.002 (2)0.003 (2)0.0042 (18)
C20.061 (2)0.063 (3)0.068 (2)0.011 (2)0.002 (2)0.0067 (19)
C30.062 (2)0.070 (3)0.063 (2)0.003 (2)0.005 (2)0.0002 (19)
C40.056 (2)0.056 (2)0.061 (2)0.002 (2)0.001 (2)0.0031 (18)
C50.058 (2)0.049 (2)0.0523 (19)0.008 (2)0.0018 (18)0.0024 (16)
C60.055 (2)0.053 (2)0.058 (2)0.001 (2)0.0077 (19)0.0052 (18)
C70.061 (3)0.049 (2)0.058 (2)0.005 (2)0.0079 (19)0.0006 (17)
C80.058 (2)0.056 (2)0.0490 (18)0.0045 (19)0.0024 (17)0.0025 (17)
C90.073 (3)0.053 (2)0.069 (2)0.006 (2)0.007 (2)0.0032 (18)
C100.079 (3)0.068 (3)0.076 (3)0.011 (3)0.004 (3)0.018 (2)
C110.073 (3)0.083 (3)0.071 (3)0.007 (3)0.013 (2)0.012 (2)
C120.070 (3)0.071 (3)0.064 (2)0.002 (2)0.006 (2)0.0033 (19)
C130.058 (2)0.060 (2)0.0494 (18)0.001 (2)0.0018 (19)0.0026 (17)
C140.071 (3)0.055 (2)0.070 (2)0.009 (2)0.001 (2)0.006 (2)
C150.075 (3)0.083 (3)0.077 (3)0.008 (3)0.014 (2)0.014 (2)
F10.0764 (17)0.0693 (16)0.121 (2)0.0121 (15)0.0069 (16)0.0145 (14)
F20.131 (2)0.0655 (15)0.0819 (16)0.0087 (18)0.0039 (18)0.0184 (12)
F30.109 (2)0.0677 (17)0.0984 (18)0.0095 (15)0.0192 (17)0.0182 (15)
N10.0595 (19)0.0510 (18)0.0576 (17)0.0011 (17)0.0032 (16)0.0014 (14)
O10.079 (2)0.0582 (16)0.0732 (18)0.0098 (17)0.0202 (18)0.0076 (13)
O20.084 (2)0.0623 (17)0.0835 (18)0.0103 (18)0.0256 (18)0.0152 (14)
Geometric parameters (Å, º) top
C1—C21.361 (6)C9—C101.380 (6)
C1—C61.413 (5)C9—H90.9300
C1—H10.9300C10—C111.367 (6)
C2—C31.389 (5)C10—H100.9300
C2—H20.9300C11—C121.371 (6)
C3—C41.370 (5)C11—H110.9300
C3—H30.9300C12—C131.392 (6)
C4—O21.367 (4)C12—H120.9300
C4—C51.409 (5)C13—C141.466 (6)
C5—O11.346 (4)C14—F11.325 (5)
C5—C61.378 (5)C14—F31.345 (5)
C6—C71.454 (5)C14—F21.348 (5)
C7—N11.270 (5)C15—O21.424 (5)
C7—H70.9300C15—H15A0.9600
C8—C91.371 (5)C15—H15B0.9600
C8—C131.414 (5)C15—H15C0.9600
C8—N11.418 (5)O1—H1A1.00 (5)
C2—C1—C6119.7 (4)C11—C10—C9120.5 (4)
C2—C1—H1120.1C11—C10—H10119.7
C6—C1—H1120.1C9—C10—H10119.7
C1—C2—C3120.4 (4)C10—C11—C12119.7 (4)
C1—C2—H2119.8C10—C11—H11120.1
C3—C2—H2119.8C12—C11—H11120.1
C4—C3—C2120.8 (4)C11—C12—C13120.9 (4)
C4—C3—H3119.6C11—C12—H12119.5
C2—C3—H3119.6C13—C12—H12119.5
O2—C4—C3125.4 (4)C12—C13—C8119.0 (4)
O2—C4—C5114.9 (3)C12—C13—C14119.9 (4)
C3—C4—C5119.7 (4)C8—C13—C14121.2 (4)
O1—C5—C6123.1 (4)F1—C14—F3105.9 (3)
O1—C5—C4117.5 (3)F1—C14—F2105.7 (4)
C6—C5—C4119.4 (4)F3—C14—F2104.4 (3)
C5—C6—C1120.1 (4)F1—C14—C13113.9 (4)
C5—C6—C7121.6 (4)F3—C14—C13112.6 (4)
C1—C6—C7118.4 (3)F2—C14—C13113.5 (4)
N1—C7—C6122.0 (3)O2—C15—H15A109.5
N1—C7—H7119.0O2—C15—H15B109.5
C6—C7—H7119.0H15A—C15—H15B109.5
C9—C8—C13118.8 (3)O2—C15—H15C109.5
C9—C8—N1124.5 (4)H15A—C15—H15C109.5
C13—C8—N1116.7 (3)H15B—C15—H15C109.5
C8—C9—C10121.1 (4)C7—N1—C8120.5 (3)
C8—C9—H9119.5C5—O1—H1A100 (3)
C10—C9—H9119.5C4—O2—C15116.9 (3)
C6—C1—C2—C30.2 (6)C9—C10—C11—C120.3 (7)
C1—C2—C3—C40.5 (6)C10—C11—C12—C130.4 (7)
C2—C3—C4—O2178.9 (4)C11—C12—C13—C81.1 (6)
C2—C3—C4—C50.4 (6)C11—C12—C13—C14179.2 (4)
O2—C4—C5—O11.2 (5)C9—C8—C13—C121.1 (5)
C3—C4—C5—O1179.8 (4)N1—C8—C13—C12178.4 (3)
O2—C4—C5—C6179.7 (3)C9—C8—C13—C14179.2 (4)
C3—C4—C5—C61.7 (5)N1—C8—C13—C141.9 (5)
O1—C5—C6—C1179.6 (4)C12—C13—C14—F1120.4 (4)
C4—C5—C6—C12.0 (5)C8—C13—C14—F159.3 (5)
O1—C5—C6—C70.8 (6)C12—C13—C14—F30.2 (6)
C4—C5—C6—C7177.6 (3)C8—C13—C14—F3179.9 (3)
C2—C1—C6—C51.1 (6)C12—C13—C14—F2118.6 (4)
C2—C1—C6—C7178.5 (3)C8—C13—C14—F261.7 (5)
C5—C6—C7—N10.6 (5)C6—C7—N1—C8178.5 (3)
C1—C6—C7—N1179.8 (4)C9—C8—N1—C719.0 (6)
C13—C8—C9—C100.4 (6)C13—C8—N1—C7163.9 (3)
N1—C8—C9—C10177.4 (4)C3—C4—O2—C154.0 (6)
C8—C9—C10—C110.3 (6)C5—C4—O2—C15177.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N11.00 (5)1.69 (5)2.625 (4)154 (4)
O1—H1A···F21.00 (5)2.57 (5)3.199 (4)121 (3)
C2—H2···F3i0.932.793.650 (5)154
C1—H1···F1i0.932.773.443 (4)130
C10—H10···O2ii0.932.473.342 (5)157
C11—H11···F3iii0.932.903.751 (5)153
C15—H15B···O1iv0.962.883.724 (6)148
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x1/2, y+3/2, z; (iv) x+1, y, z.
 

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