Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028486/wk2054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028486/wk2054Isup2.hkl |
CCDC reference: 654945
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
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.
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 C═N 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).
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.
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. |
C19H13F4NO | F(000) = 712 |
Mr = 347.30 | Dx = 1.455 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2493 reflections |
a = 14.815 (9) Å | θ = 2.4–24.5° |
b = 6.192 (4) Å | µ = 0.12 mm−1 |
c = 17.989 (11) Å | T = 298 K |
β = 106.127 (11)° | Block, colourless |
V = 1585.3 (17) Å3 | 0.38 × 0.31 × 0.19 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 2841 independent reflections |
Radiation source: fine-focus sealed tube | 2522 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 25.2°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→16 |
Tmin = 0.955, Tmax = 0.977 | k = −7→6 |
7985 measured reflections | l = −19→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.096 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.206 | H-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 parameters | Δρmax = 0.64 e Å−3 |
138 restraints | Δρmin = −0.46 e Å−3 |
C19H13F4NO | V = 1585.3 (17) Å3 |
Mr = 347.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.815 (9) Å | µ = 0.12 mm−1 |
b = 6.192 (4) Å | T = 298 K |
c = 17.989 (11) Å | 0.38 × 0.31 × 0.19 mm |
β = 106.127 (11)° |
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 = 0.977 | Rint = 0.021 |
7985 measured reflections |
R[F2 > 2σ(F2)] = 0.096 | 138 restraints |
wR(F2) = 0.206 | H-atom parameters constrained |
S = 1.15 | Δρmax = 0.64 e Å−3 |
2841 reflections | Δρmin = −0.46 e Å−3 |
240 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.9123 (9) | 0.7965 (18) | 0.0535 (5) | 0.0750 (14) | 0.391 (4) |
F1 | 0.9885 (6) | 0.6777 (17) | 0.0554 (7) | 0.117 (2) | 0.391 (4) |
F2 | 0.9043 (6) | 0.9304 (19) | −0.0065 (5) | 0.1122 (19) | 0.391 (4) |
F3 | 0.9411 (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) |
F4 | 0.58472 (16) | 0.3569 (4) | 0.03359 (14) | 0.0622 (7) | |
O1 | 0.1144 (2) | 1.0983 (5) | 0.24659 (18) | 0.0684 (9) | |
N1 | 0.6066 (2) | 0.7862 (5) | 0.09222 (17) | 0.0468 (8) | |
C2 | 0.8304 (3) | 0.6720 (6) | 0.0503 (2) | 0.0505 (10) | |
C3 | 0.7613 (3) | 0.7712 (6) | 0.0756 (2) | 0.0489 (9) | |
H3 | 0.7713 | 0.9101 | 0.0959 | 0.059* | |
C4 | 0.6768 (2) | 0.6681 (6) | 0.07158 (19) | 0.0414 (8) | |
C5 | 0.6658 (3) | 0.4624 (6) | 0.0399 (2) | 0.0448 (9) | |
C6 | 0.7326 (3) | 0.3628 (6) | 0.0121 (2) | 0.0530 (10) | |
H6 | 0.7217 | 0.2265 | −0.0103 | 0.064* | |
C7 | 0.8160 (3) | 0.4681 (7) | 0.0181 (2) | 0.0563 (11) | |
H7 | 0.8625 | 0.4022 | 0.0004 | 0.068* | |
C8 | 0.5562 (3) | 0.6978 (6) | 0.1298 (2) | 0.0457 (9) | |
H8 | 0.5699 | 0.5575 | 0.1478 | 0.055* | |
C9 | 0.4770 (2) | 0.8105 (6) | 0.14573 (19) | 0.0426 (8) | |
C10 | 0.4475 (3) | 1.0150 (6) | 0.1130 (2) | 0.0451 (9) | |
H10 | 0.4803 | 1.0817 | 0.0821 | 0.054* | |
C11 | 0.3723 (3) | 1.1148 (6) | 0.1261 (2) | 0.0462 (9) | |
H11 | 0.3541 | 1.2493 | 0.1041 | 0.055* | |
C12 | 0.3205 (2) | 1.0184 (6) | 0.17287 (19) | 0.0434 (9) | |
C13 | 0.2404 (3) | 1.1187 (7) | 0.1858 (2) | 0.0499 (9) | |
H13 | 0.2203 | 1.2517 | 0.1632 | 0.060* | |
C14 | 0.1926 (3) | 1.0203 (7) | 0.2314 (2) | 0.0532 (10) | |
C15 | 0.2244 (3) | 0.8213 (7) | 0.2667 (2) | 0.0573 (11) | |
H15 | 0.1922 | 0.7574 | 0.2987 | 0.069* | |
C16 | 0.3005 (3) | 0.7208 (7) | 0.2554 (2) | 0.0536 (10) | |
H16 | 0.3199 | 0.5892 | 0.2794 | 0.064* | |
C17 | 0.3506 (3) | 0.8145 (6) | 0.20723 (19) | 0.0429 (8) | |
C18 | 0.4291 (3) | 0.7146 (6) | 0.1921 (2) | 0.0454 (9) | |
H18 | 0.4488 | 0.5806 | 0.2140 | 0.054* | |
C19 | 0.0753 (3) | 1.2934 (8) | 0.2097 (3) | 0.0781 (14) | |
H19A | 0.1204 | 1.4078 | 0.2250 | 0.117* | |
H19B | 0.0198 | 1.3289 | 0.2247 | 0.117* | |
H19C | 0.0594 | 1.2752 | 0.1546 | 0.117* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
F4 | 0.0546 (14) | 0.0554 (14) | 0.0793 (16) | −0.0163 (11) | 0.0231 (12) | −0.0134 (12) |
O1 | 0.0547 (18) | 0.081 (2) | 0.076 (2) | 0.0017 (16) | 0.0305 (15) | −0.0072 (17) |
N1 | 0.0472 (18) | 0.0431 (17) | 0.0500 (18) | −0.0024 (15) | 0.0132 (14) | −0.0003 (14) |
C2 | 0.046 (2) | 0.049 (2) | 0.057 (2) | 0.0012 (18) | 0.0135 (18) | 0.0055 (19) |
C3 | 0.056 (2) | 0.040 (2) | 0.049 (2) | −0.0023 (18) | 0.0116 (18) | −0.0020 (17) |
C4 | 0.0406 (19) | 0.043 (2) | 0.0407 (19) | 0.0007 (16) | 0.0109 (15) | 0.0040 (16) |
C5 | 0.046 (2) | 0.042 (2) | 0.045 (2) | −0.0059 (17) | 0.0112 (16) | 0.0042 (16) |
C6 | 0.061 (2) | 0.041 (2) | 0.057 (2) | 0.0018 (19) | 0.0175 (19) | −0.0049 (18) |
C7 | 0.048 (2) | 0.054 (2) | 0.071 (3) | 0.0071 (19) | 0.025 (2) | 0.000 (2) |
C8 | 0.050 (2) | 0.040 (2) | 0.045 (2) | 0.0002 (17) | 0.0091 (17) | −0.0006 (16) |
C9 | 0.047 (2) | 0.043 (2) | 0.0376 (18) | −0.0030 (17) | 0.0097 (15) | −0.0026 (16) |
C10 | 0.050 (2) | 0.043 (2) | 0.046 (2) | −0.0048 (17) | 0.0186 (17) | 0.0044 (16) |
C11 | 0.055 (2) | 0.0365 (19) | 0.047 (2) | −0.0023 (17) | 0.0147 (17) | 0.0056 (16) |
C12 | 0.047 (2) | 0.044 (2) | 0.0373 (18) | −0.0037 (17) | 0.0086 (15) | −0.0049 (16) |
C13 | 0.051 (2) | 0.048 (2) | 0.050 (2) | 0.0021 (18) | 0.0120 (18) | −0.0052 (18) |
C14 | 0.047 (2) | 0.063 (3) | 0.051 (2) | −0.008 (2) | 0.0166 (18) | −0.011 (2) |
C15 | 0.062 (3) | 0.061 (3) | 0.055 (2) | −0.013 (2) | 0.028 (2) | 0.001 (2) |
C16 | 0.064 (3) | 0.048 (2) | 0.052 (2) | −0.006 (2) | 0.0215 (19) | 0.0047 (18) |
C17 | 0.048 (2) | 0.041 (2) | 0.0399 (18) | −0.0042 (17) | 0.0130 (16) | −0.0023 (16) |
C18 | 0.055 (2) | 0.0383 (19) | 0.0400 (19) | 0.0001 (17) | 0.0091 (16) | 0.0024 (16) |
C19 | 0.061 (3) | 0.077 (3) | 0.103 (4) | 0.007 (3) | 0.033 (3) | −0.017 (3) |
C1—F1 | 1.3396 (12) | C8—C9 | 1.460 (5) |
C1—F2 | 1.3399 (12) | C8—H8 | 0.9300 |
C1—F3 | 1.3400 (12) | C9—C18 | 1.371 (5) |
C1—C2 | 1.425 (15) | C9—C10 | 1.414 (5) |
C1'—F2' | 1.3395 (13) | C10—C11 | 1.352 (5) |
C1'—F1' | 1.3396 (12) | C10—H10 | 0.9300 |
C1'—F3' | 1.3399 (13) | C11—C12 | 1.417 (5) |
C1'—C2 | 1.486 (10) | C11—H11 | 0.9300 |
F4—C5 | 1.344 (4) | C12—C13 | 1.414 (5) |
O1—C14 | 1.352 (5) | C12—C17 | 1.422 (5) |
O1—C19 | 1.421 (6) | C13—C14 | 1.368 (5) |
N1—C8 | 1.263 (5) | C13—H13 | 0.9300 |
N1—C4 | 1.404 (5) | C14—C15 | 1.406 (6) |
C2—C3 | 1.376 (5) | C15—C16 | 1.352 (6) |
C2—C7 | 1.381 (6) | C15—H15 | 0.9300 |
C3—C4 | 1.388 (5) | C16—C17 | 1.413 (5) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.386 (5) | C17—C18 | 1.409 (5) |
C5—C6 | 1.373 (5) | C18—H18 | 0.9300 |
C6—C7 | 1.374 (6) | C19—H19A | 0.9600 |
C6—H6 | 0.9300 | C19—H19B | 0.9600 |
C7—H7 | 0.9300 | C19—H19C | 0.9600 |
F1—C1—F2 | 104.3 (9) | C9—C8—H8 | 119.2 |
F1—C1—F3 | 103.8 (9) | C18—C9—C10 | 119.3 (3) |
F2—C1—F3 | 103.0 (9) | C18—C9—C8 | 119.5 (3) |
F1—C1—C2 | 113.9 (9) | C10—C9—C8 | 121.2 (3) |
F2—C1—C2 | 114.7 (9) | C11—C10—C9 | 120.7 (3) |
F3—C1—C2 | 115.7 (10) | C11—C10—H10 | 119.6 |
F2'—C1'—F1' | 104.8 (5) | C9—C10—H10 | 119.6 |
F2'—C1'—F3' | 107.1 (6) | C10—C11—C12 | 121.3 (3) |
F1'—C1'—F3' | 104.6 (6) | C10—C11—H11 | 119.3 |
F2'—C1'—C2 | 112.3 (5) | C12—C11—H11 | 119.3 |
F1'—C1'—C2 | 113.3 (6) | C13—C12—C11 | 122.0 (4) |
F3'—C1'—C2 | 113.9 (6) | C13—C12—C17 | 119.7 (3) |
C14—O1—C19 | 118.0 (4) | C11—C12—C17 | 118.4 (3) |
C8—N1—C4 | 120.5 (3) | C14—C13—C12 | 120.0 (4) |
C3—C2—C7 | 120.3 (4) | C14—C13—H13 | 120.0 |
C3—C2—C1 | 116.7 (5) | C12—C13—H13 | 120.0 |
C7—C2—C1 | 122.9 (5) | O1—C14—C13 | 125.3 (4) |
C3—C2—C1' | 120.5 (4) | O1—C14—C15 | 114.8 (4) |
C7—C2—C1' | 119.3 (4) | C13—C14—C15 | 119.9 (4) |
C1—C2—C1' | 5.5 (4) | C16—C15—C14 | 121.5 (4) |
C2—C3—C4 | 121.4 (4) | C16—C15—H15 | 119.2 |
C2—C3—H3 | 119.3 | C14—C15—H15 | 119.2 |
C4—C3—H3 | 119.3 | C15—C16—C17 | 120.4 (4) |
C5—C4—C3 | 116.4 (3) | C15—C16—H16 | 119.8 |
C5—C4—N1 | 125.2 (3) | C17—C16—H16 | 119.8 |
C3—C4—N1 | 118.1 (3) | C18—C17—C16 | 122.8 (4) |
F4—C5—C6 | 117.9 (3) | C18—C17—C12 | 118.8 (3) |
F4—C5—C4 | 118.8 (3) | C16—C17—C12 | 118.4 (3) |
C6—C5—C4 | 123.2 (3) | C9—C18—C17 | 121.5 (3) |
C5—C6—C7 | 118.8 (4) | C9—C18—H18 | 119.3 |
C5—C6—H6 | 120.6 | C17—C18—H18 | 119.3 |
C7—C6—H6 | 120.6 | O1—C19—H19A | 109.5 |
C6—C7—C2 | 119.9 (4) | O1—C19—H19B | 109.5 |
C6—C7—H7 | 120.1 | H19A—C19—H19B | 109.5 |
C2—C7—H7 | 120.1 | O1—C19—H19C | 109.5 |
N1—C8—C9 | 121.7 (3) | H19A—C19—H19C | 109.5 |
N1—C8—H8 | 119.2 | H19B—C19—H19C | 109.5 |
F1—C1—C2—C3 | 157.3 (6) | C5—C6—C7—C2 | −1.2 (6) |
F2—C1—C2—C3 | −82.6 (8) | C3—C2—C7—C6 | −0.7 (6) |
F3—C1—C2—C3 | 37.1 (8) | C1—C2—C7—C6 | −175.6 (5) |
F1—C1—C2—C7 | −27.6 (8) | C1'—C2—C7—C6 | 179.5 (4) |
F2—C1—C2—C7 | 92.4 (7) | C4—N1—C8—C9 | −174.1 (3) |
F3—C1—C2—C7 | −147.8 (6) | N1—C8—C9—C18 | −174.7 (3) |
F1—C1—C2—C1' | 23 (4) | N1—C8—C9—C10 | 6.5 (5) |
F2—C1—C2—C1' | 143 (5) | C18—C9—C10—C11 | −0.9 (5) |
F3—C1—C2—C1' | −98 (4) | C8—C9—C10—C11 | 177.9 (3) |
F2'—C1'—C2—C3 | −136.8 (5) | C9—C10—C11—C12 | 0.0 (5) |
F1'—C1'—C2—C3 | 104.7 (5) | C10—C11—C12—C13 | −178.6 (3) |
F3'—C1'—C2—C3 | −14.8 (6) | C10—C11—C12—C17 | 1.2 (5) |
F2'—C1'—C2—C7 | 42.9 (6) | C11—C12—C13—C14 | −179.9 (3) |
F1'—C1'—C2—C7 | −75.6 (6) | C17—C12—C13—C14 | 0.3 (5) |
F3'—C1'—C2—C7 | 164.9 (5) | C19—O1—C14—C13 | 3.1 (6) |
F2'—C1'—C2—C1 | −89 (4) | C19—O1—C14—C15 | −176.9 (4) |
F1'—C1'—C2—C1 | 152 (5) | C12—C13—C14—O1 | −178.6 (3) |
F3'—C1'—C2—C1 | 33 (4) | C12—C13—C14—C15 | 1.3 (6) |
C7—C2—C3—C4 | 1.8 (6) | O1—C14—C15—C16 | 178.4 (4) |
C1—C2—C3—C4 | 177.0 (5) | C13—C14—C15—C16 | −1.6 (6) |
C1'—C2—C3—C4 | −178.5 (4) | C14—C15—C16—C17 | 0.1 (6) |
C2—C3—C4—C5 | −0.8 (5) | C15—C16—C17—C18 | −178.6 (4) |
C2—C3—C4—N1 | −174.5 (3) | C15—C16—C17—C12 | 1.5 (6) |
C8—N1—C4—C5 | 45.9 (5) | C13—C12—C17—C18 | 178.4 (3) |
C8—N1—C4—C3 | −141.0 (4) | C11—C12—C17—C18 | −1.4 (5) |
C3—C4—C5—F4 | −179.0 (3) | C13—C12—C17—C16 | −1.8 (5) |
N1—C4—C5—F4 | −5.8 (5) | C11—C12—C17—C16 | 178.4 (3) |
C3—C4—C5—C6 | −1.2 (5) | C10—C9—C18—C17 | 0.6 (5) |
N1—C4—C5—C6 | 172.1 (4) | C8—C9—C18—C17 | −178.2 (3) |
F4—C5—C6—C7 | −180.0 (3) | C16—C17—C18—C9 | −179.3 (3) |
C4—C5—C6—C7 | 2.2 (6) | C12—C17—C18—C9 | 0.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···F3 | 0.93 | 2.45 | 2.737 (14) | 98 |
C8—H8···F4 | 0.93 | 2.46 | 2.835 (4) | 104 |
Experimental details
Crystal data | |
Chemical formula | C19H13F4NO |
Mr | 347.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 14.815 (9), 6.192 (4), 17.989 (11) |
β (°) | 106.127 (11) |
V (Å3) | 1585.3 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.38 × 0.31 × 0.19 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.955, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7985, 2841, 2522 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.096, 0.206, 1.15 |
No. of reflections | 2841 |
No. of parameters | 240 |
No. of restraints | 138 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.46 |
Computer programs: SMART (Bruker,1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···F3 | 0.93 | 2.45 | 2.737 (14) | 98.2 |
C8—H8···F4 | 0.93 | 2.46 | 2.835 (4) | 104.0 |
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 C═N 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.