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In the title Schiff base, C19H13F4NO, there is intra­molecular C—H...F hydrogen bonding. A C—H...π inter­action of 3.97 (6) Å forms an infinite tape parallel to the c axis. The trifluoro­methyl group is disordered over two positions, with site occupancy factors of approximately 0.6:0.4.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028486/wk2054sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028486/wk2054Isup2.hkl
Contains datablock I

CCDC reference: 654945

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.096
  • wR factor = 0.206
  • Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT482_ALERT_4_C Small D-H..A Angle Rep for C3 .. F3 .. 98.20 Deg. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 5.50 Deg. C1 -C2 -C1' 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 138
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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

Comment top

Schiff base ligands have significant importance in chemistry, especially in the development of Schiff base complexes, (Johnson et al., 1996; Alizadeh et al., 1999; Wang & Zheng, 2007). Schiff bases that have solvent-dependent UV/vis spectra (solvatochromicity) can be suitable NLO (nonlinear optically active) materials (Alemi & Shaabani, 2000). They are also useful in the asymmetric oxidation of methyl phenyl sulfide and can be enantioselective (Kim & Shim, 1999). In this paper, we report the synthesis and crystal structure of the title compound, (I).

The molecular structure of the title compound (Fig. 1) contains one intermolecular hydrogen bonds (C3—H3···F3; C8—H8···F4) (Table 1). The C8—N1 bond length is 1.262 (4) Å, indicative of a CN double bond. The C—F, C—O and C—C distances are unremarkable (Table.1).

Intramolecular C—H···F hydrogen bonding and C—H···/p interaction form an infinite tape parallel to the c axis.

Related literature top

For related literature, see: Alemi & Shaabani (2000); Alizadeh et al. (1999); Kim & Shin (1999); Johnson et al. (1996); Wang & Zheng (2007).

Experimental top

Under nitrogen, a mixture of 6-methoxy-1-naphthaldehyde (1.87 g,10 mmol), Na2SO4 (3.0 g) and 5-fluoro-2-trifluoromethylaniline (1.58 g, 10 mmol) in absolute ethanol (20 ml) was refluxed for about 12 h to yield a yellow precipitate. The product was collected by vacuum filtration and washed with ethanol. The crude solid was redissolved in CH2Cl2 (100 ml) and washed with water (2 x 15 ml) and brine (8 ml). After drying over Na2SO4, the solvent was removed under vacuum, and a yellow solid was isolated in 92% yield (3.1 g). Colourless single crystals of the Schiff base, (I), suitable for X-ray analysis were grown from CH2Cl2 and absolute ethanol (4:1) by slow evaporation of the solvents at room temperature over a period of about one week.

Refinement top

All H atoms were placed in calculated positions [Csp2—H = 0.93 Å] and refined using a riding model, with Uiso(H) = 1.2 Ueq(C). The trifluoromethyl group was found to be disordered, the two components being rotated by about 60°. Atoms C1, F1, F2 and F3 were refined over two positions [occupancies 0.609 (4) for the primed and 0.391 (4) for the unprimed atoms] and the C—F distances restrained.

Structure description top

Schiff base ligands have significant importance in chemistry, especially in the development of Schiff base complexes, (Johnson et al., 1996; Alizadeh et al., 1999; Wang & Zheng, 2007). Schiff bases that have solvent-dependent UV/vis spectra (solvatochromicity) can be suitable NLO (nonlinear optically active) materials (Alemi & Shaabani, 2000). They are also useful in the asymmetric oxidation of methyl phenyl sulfide and can be enantioselective (Kim & Shim, 1999). In this paper, we report the synthesis and crystal structure of the title compound, (I).

The molecular structure of the title compound (Fig. 1) contains one intermolecular hydrogen bonds (C3—H3···F3; C8—H8···F4) (Table 1). The C8—N1 bond length is 1.262 (4) Å, indicative of a CN double bond. The C—F, C—O and C—C distances are unremarkable (Table.1).

Intramolecular C—H···F hydrogen bonding and C—H···/p interaction form an infinite tape parallel to the c axis.

For related literature, see: Alemi & Shaabani (2000); Alizadeh et al. (1999); Kim & Shin (1999); Johnson et al. (1996); Wang & Zheng (2007).

Computing details top

Data collection: SMART (Bruker,1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atomic numbering scheme (CF3 component is disordered). Probability displacement ellipsoids are drawn at the 30% level.
2-Fluoro-N-[(E)-1-(6-methoxy-2-naphthyl)methylidene]-5-(trifluoromethyl)aniline top
Crystal data top
C19H13F4NOF(000) = 712
Mr = 347.30Dx = 1.455 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2493 reflections
a = 14.815 (9) Åθ = 2.4–24.5°
b = 6.192 (4) ŵ = 0.12 mm1
c = 17.989 (11) ÅT = 298 K
β = 106.127 (11)°Block, colourless
V = 1585.3 (17) Å30.38 × 0.31 × 0.19 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
2841 independent reflections
Radiation source: fine-focus sealed tube2522 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 25.2°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1716
Tmin = 0.955, Tmax = 0.977k = 76
7985 measured reflectionsl = 1921
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)] = 0.096Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0567P)2 + 2.7345P]
where P = (Fo2 + 2Fc2)/3
2841 reflections(Δ/σ)max = 0.001
240 parametersΔρmax = 0.64 e Å3
138 restraintsΔρmin = 0.46 e Å3
Crystal data top
C19H13F4NOV = 1585.3 (17) Å3
Mr = 347.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.815 (9) ŵ = 0.12 mm1
b = 6.192 (4) ÅT = 298 K
c = 17.989 (11) Å0.38 × 0.31 × 0.19 mm
β = 106.127 (11)°
Data collection top
Bruker APEX area-detector
diffractometer
2841 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2522 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.977Rint = 0.021
7985 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.096138 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.15Δρmax = 0.64 e Å3
2841 reflectionsΔρmin = 0.46 e Å3
240 parameters
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)
C10.9123 (9)0.7965 (18)0.0535 (5)0.0750 (14)0.391 (4)
F10.9885 (6)0.6777 (17)0.0554 (7)0.117 (2)0.391 (4)
F20.9043 (6)0.9304 (19)0.0065 (5)0.1122 (19)0.391 (4)
F30.9411 (9)0.9277 (17)0.1148 (6)0.119 (2)0.391 (4)
C1'0.9213 (6)0.7832 (10)0.0569 (3)0.0750 (14)0.609 (4)
F1'0.9923 (4)0.7061 (11)0.1142 (4)0.117 (2)0.609 (4)
F2'0.9500 (4)0.7608 (12)0.0071 (3)0.1122 (19)0.609 (4)
F3'0.9197 (6)0.9953 (10)0.0713 (5)0.119 (2)0.609 (4)
F40.58472 (16)0.3569 (4)0.03359 (14)0.0622 (7)
O10.1144 (2)1.0983 (5)0.24659 (18)0.0684 (9)
N10.6066 (2)0.7862 (5)0.09222 (17)0.0468 (8)
C20.8304 (3)0.6720 (6)0.0503 (2)0.0505 (10)
C30.7613 (3)0.7712 (6)0.0756 (2)0.0489 (9)
H30.77130.91010.09590.059*
C40.6768 (2)0.6681 (6)0.07158 (19)0.0414 (8)
C50.6658 (3)0.4624 (6)0.0399 (2)0.0448 (9)
C60.7326 (3)0.3628 (6)0.0121 (2)0.0530 (10)
H60.72170.22650.01030.064*
C70.8160 (3)0.4681 (7)0.0181 (2)0.0563 (11)
H70.86250.40220.00040.068*
C80.5562 (3)0.6978 (6)0.1298 (2)0.0457 (9)
H80.56990.55750.14780.055*
C90.4770 (2)0.8105 (6)0.14573 (19)0.0426 (8)
C100.4475 (3)1.0150 (6)0.1130 (2)0.0451 (9)
H100.48031.08170.08210.054*
C110.3723 (3)1.1148 (6)0.1261 (2)0.0462 (9)
H110.35411.24930.10410.055*
C120.3205 (2)1.0184 (6)0.17287 (19)0.0434 (9)
C130.2404 (3)1.1187 (7)0.1858 (2)0.0499 (9)
H130.22031.25170.16320.060*
C140.1926 (3)1.0203 (7)0.2314 (2)0.0532 (10)
C150.2244 (3)0.8213 (7)0.2667 (2)0.0573 (11)
H150.19220.75740.29870.069*
C160.3005 (3)0.7208 (7)0.2554 (2)0.0536 (10)
H160.31990.58920.27940.064*
C170.3506 (3)0.8145 (6)0.20723 (19)0.0429 (8)
C180.4291 (3)0.7146 (6)0.1921 (2)0.0454 (9)
H180.44880.58060.21400.054*
C190.0753 (3)1.2934 (8)0.2097 (3)0.0781 (14)
H19A0.12041.40780.22500.117*
H19B0.01981.32890.22470.117*
H19C0.05941.27520.15460.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.053 (3)0.064 (3)0.120 (4)0.009 (2)0.045 (3)0.005 (3)
F10.050 (2)0.147 (4)0.142 (5)0.017 (2)0.006 (4)0.030 (5)
F20.085 (4)0.158 (5)0.111 (3)0.054 (3)0.055 (3)0.012 (4)
F30.084 (4)0.074 (4)0.208 (8)0.032 (3)0.057 (5)0.009 (4)
C1'0.053 (3)0.064 (3)0.120 (4)0.009 (2)0.045 (3)0.005 (3)
F1'0.050 (2)0.147 (4)0.142 (5)0.017 (2)0.006 (4)0.030 (5)
F2'0.085 (4)0.158 (5)0.111 (3)0.054 (3)0.055 (3)0.012 (4)
F3'0.084 (4)0.074 (4)0.208 (8)0.032 (3)0.057 (5)0.009 (4)
F40.0546 (14)0.0554 (14)0.0793 (16)0.0163 (11)0.0231 (12)0.0134 (12)
O10.0547 (18)0.081 (2)0.076 (2)0.0017 (16)0.0305 (15)0.0072 (17)
N10.0472 (18)0.0431 (17)0.0500 (18)0.0024 (15)0.0132 (14)0.0003 (14)
C20.046 (2)0.049 (2)0.057 (2)0.0012 (18)0.0135 (18)0.0055 (19)
C30.056 (2)0.040 (2)0.049 (2)0.0023 (18)0.0116 (18)0.0020 (17)
C40.0406 (19)0.043 (2)0.0407 (19)0.0007 (16)0.0109 (15)0.0040 (16)
C50.046 (2)0.042 (2)0.045 (2)0.0059 (17)0.0112 (16)0.0042 (16)
C60.061 (2)0.041 (2)0.057 (2)0.0018 (19)0.0175 (19)0.0049 (18)
C70.048 (2)0.054 (2)0.071 (3)0.0071 (19)0.025 (2)0.000 (2)
C80.050 (2)0.040 (2)0.045 (2)0.0002 (17)0.0091 (17)0.0006 (16)
C90.047 (2)0.043 (2)0.0376 (18)0.0030 (17)0.0097 (15)0.0026 (16)
C100.050 (2)0.043 (2)0.046 (2)0.0048 (17)0.0186 (17)0.0044 (16)
C110.055 (2)0.0365 (19)0.047 (2)0.0023 (17)0.0147 (17)0.0056 (16)
C120.047 (2)0.044 (2)0.0373 (18)0.0037 (17)0.0086 (15)0.0049 (16)
C130.051 (2)0.048 (2)0.050 (2)0.0021 (18)0.0120 (18)0.0052 (18)
C140.047 (2)0.063 (3)0.051 (2)0.008 (2)0.0166 (18)0.011 (2)
C150.062 (3)0.061 (3)0.055 (2)0.013 (2)0.028 (2)0.001 (2)
C160.064 (3)0.048 (2)0.052 (2)0.006 (2)0.0215 (19)0.0047 (18)
C170.048 (2)0.041 (2)0.0399 (18)0.0042 (17)0.0130 (16)0.0023 (16)
C180.055 (2)0.0383 (19)0.0400 (19)0.0001 (17)0.0091 (16)0.0024 (16)
C190.061 (3)0.077 (3)0.103 (4)0.007 (3)0.033 (3)0.017 (3)
Geometric parameters (Å, º) top
C1—F11.3396 (12)C8—C91.460 (5)
C1—F21.3399 (12)C8—H80.9300
C1—F31.3400 (12)C9—C181.371 (5)
C1—C21.425 (15)C9—C101.414 (5)
C1'—F2'1.3395 (13)C10—C111.352 (5)
C1'—F1'1.3396 (12)C10—H100.9300
C1'—F3'1.3399 (13)C11—C121.417 (5)
C1'—C21.486 (10)C11—H110.9300
F4—C51.344 (4)C12—C131.414 (5)
O1—C141.352 (5)C12—C171.422 (5)
O1—C191.421 (6)C13—C141.368 (5)
N1—C81.263 (5)C13—H130.9300
N1—C41.404 (5)C14—C151.406 (6)
C2—C31.376 (5)C15—C161.352 (6)
C2—C71.381 (6)C15—H150.9300
C3—C41.388 (5)C16—C171.413 (5)
C3—H30.9300C16—H160.9300
C4—C51.386 (5)C17—C181.409 (5)
C5—C61.373 (5)C18—H180.9300
C6—C71.374 (6)C19—H19A0.9600
C6—H60.9300C19—H19B0.9600
C7—H70.9300C19—H19C0.9600
F1—C1—F2104.3 (9)C9—C8—H8119.2
F1—C1—F3103.8 (9)C18—C9—C10119.3 (3)
F2—C1—F3103.0 (9)C18—C9—C8119.5 (3)
F1—C1—C2113.9 (9)C10—C9—C8121.2 (3)
F2—C1—C2114.7 (9)C11—C10—C9120.7 (3)
F3—C1—C2115.7 (10)C11—C10—H10119.6
F2'—C1'—F1'104.8 (5)C9—C10—H10119.6
F2'—C1'—F3'107.1 (6)C10—C11—C12121.3 (3)
F1'—C1'—F3'104.6 (6)C10—C11—H11119.3
F2'—C1'—C2112.3 (5)C12—C11—H11119.3
F1'—C1'—C2113.3 (6)C13—C12—C11122.0 (4)
F3'—C1'—C2113.9 (6)C13—C12—C17119.7 (3)
C14—O1—C19118.0 (4)C11—C12—C17118.4 (3)
C8—N1—C4120.5 (3)C14—C13—C12120.0 (4)
C3—C2—C7120.3 (4)C14—C13—H13120.0
C3—C2—C1116.7 (5)C12—C13—H13120.0
C7—C2—C1122.9 (5)O1—C14—C13125.3 (4)
C3—C2—C1'120.5 (4)O1—C14—C15114.8 (4)
C7—C2—C1'119.3 (4)C13—C14—C15119.9 (4)
C1—C2—C1'5.5 (4)C16—C15—C14121.5 (4)
C2—C3—C4121.4 (4)C16—C15—H15119.2
C2—C3—H3119.3C14—C15—H15119.2
C4—C3—H3119.3C15—C16—C17120.4 (4)
C5—C4—C3116.4 (3)C15—C16—H16119.8
C5—C4—N1125.2 (3)C17—C16—H16119.8
C3—C4—N1118.1 (3)C18—C17—C16122.8 (4)
F4—C5—C6117.9 (3)C18—C17—C12118.8 (3)
F4—C5—C4118.8 (3)C16—C17—C12118.4 (3)
C6—C5—C4123.2 (3)C9—C18—C17121.5 (3)
C5—C6—C7118.8 (4)C9—C18—H18119.3
C5—C6—H6120.6C17—C18—H18119.3
C7—C6—H6120.6O1—C19—H19A109.5
C6—C7—C2119.9 (4)O1—C19—H19B109.5
C6—C7—H7120.1H19A—C19—H19B109.5
C2—C7—H7120.1O1—C19—H19C109.5
N1—C8—C9121.7 (3)H19A—C19—H19C109.5
N1—C8—H8119.2H19B—C19—H19C109.5
F1—C1—C2—C3157.3 (6)C5—C6—C7—C21.2 (6)
F2—C1—C2—C382.6 (8)C3—C2—C7—C60.7 (6)
F3—C1—C2—C337.1 (8)C1—C2—C7—C6175.6 (5)
F1—C1—C2—C727.6 (8)C1'—C2—C7—C6179.5 (4)
F2—C1—C2—C792.4 (7)C4—N1—C8—C9174.1 (3)
F3—C1—C2—C7147.8 (6)N1—C8—C9—C18174.7 (3)
F1—C1—C2—C1'23 (4)N1—C8—C9—C106.5 (5)
F2—C1—C2—C1'143 (5)C18—C9—C10—C110.9 (5)
F3—C1—C2—C1'98 (4)C8—C9—C10—C11177.9 (3)
F2'—C1'—C2—C3136.8 (5)C9—C10—C11—C120.0 (5)
F1'—C1'—C2—C3104.7 (5)C10—C11—C12—C13178.6 (3)
F3'—C1'—C2—C314.8 (6)C10—C11—C12—C171.2 (5)
F2'—C1'—C2—C742.9 (6)C11—C12—C13—C14179.9 (3)
F1'—C1'—C2—C775.6 (6)C17—C12—C13—C140.3 (5)
F3'—C1'—C2—C7164.9 (5)C19—O1—C14—C133.1 (6)
F2'—C1'—C2—C189 (4)C19—O1—C14—C15176.9 (4)
F1'—C1'—C2—C1152 (5)C12—C13—C14—O1178.6 (3)
F3'—C1'—C2—C133 (4)C12—C13—C14—C151.3 (6)
C7—C2—C3—C41.8 (6)O1—C14—C15—C16178.4 (4)
C1—C2—C3—C4177.0 (5)C13—C14—C15—C161.6 (6)
C1'—C2—C3—C4178.5 (4)C14—C15—C16—C170.1 (6)
C2—C3—C4—C50.8 (5)C15—C16—C17—C18178.6 (4)
C2—C3—C4—N1174.5 (3)C15—C16—C17—C121.5 (6)
C8—N1—C4—C545.9 (5)C13—C12—C17—C18178.4 (3)
C8—N1—C4—C3141.0 (4)C11—C12—C17—C181.4 (5)
C3—C4—C5—F4179.0 (3)C13—C12—C17—C161.8 (5)
N1—C4—C5—F45.8 (5)C11—C12—C17—C16178.4 (3)
C3—C4—C5—C61.2 (5)C10—C9—C18—C170.6 (5)
N1—C4—C5—C6172.1 (4)C8—C9—C18—C17178.2 (3)
F4—C5—C6—C7180.0 (3)C16—C17—C18—C9179.3 (3)
C4—C5—C6—C72.2 (6)C12—C17—C18—C90.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···F30.932.452.737 (14)98
C8—H8···F40.932.462.835 (4)104

Experimental details

Crystal data
Chemical formulaC19H13F4NO
Mr347.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)14.815 (9), 6.192 (4), 17.989 (11)
β (°) 106.127 (11)
V3)1585.3 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.38 × 0.31 × 0.19
Data collection
DiffractometerBruker APEX area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.955, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
7985, 2841, 2522
Rint0.021
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.096, 0.206, 1.15
No. of reflections2841
No. of parameters240
No. of restraints138
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.46

Computer programs: SMART (Bruker,1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···F30.932.452.737 (14)98.2
C8—H8···F40.932.462.835 (4)104.0
 

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