Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030310/ez2084sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030310/ez2084Isup2.hkl |
CCDC reference: 659095
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.076
- wR factor = 0.257
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.257 PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.61 Sigma PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT084_ALERT_2_C High R2 Value .................................. 0.26 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
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 27.90 From the CIF: _reflns_number_total 1809 Count of symmetry unique reflns 1811 Completeness (_total/calc) 99.89% 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 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 60
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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
For related literature, see: Moustakali-Mavridis et al. (1978); Umezawa et al. (1999); Hadjoudis et al. (1987); Sorell (1989); Gelling & Feringa (1990); Dutta et al. (1997); Bernstein et al. (1995); Ersanlı et al. (2004); Jacobsen (1993); Karadayı et al. (2003); Ligtenbarg et al. (1999); Pyrz et al. (1991); Spek (1997); Xu et al. (1994); Şahin et al. (2005).
The compound (E)-2-methyl-6-[(3-(trifluoromethyl)phenylimino)methyl] phenol was prepared by refluxing a mixture of a solution containing 3-methylsalicylaldehyde (0.1 ml, 0.82 mmol) in 20 ml e thanol and a solution containing 3-aminobenzotrifluoride (0.13 g, 0.82 mmol) in 20 ml e thanol. The reaction mixture was stirred for 2 h under reflux. Crystals of (E)-2-methyl-6-[(3-(trifluoromethyl)phenylimino)methyl] phenol suitable for X-ray analysis were obtained from ethanol by slow evaporation (yield 62%; m.p. 361–363 K).
The high s.u. values and high displacement parameters of some atoms in the molecule are likely caused by disorder. The CF3 group shows rotational disorder. The disordered trifluoromethyl F atoms were refined anisotropically, with geometrical and displacement parameter restraints for the two sets of positions; the refined occupancy factors are 0.494 (5) and 0.506 (5).
Refinement of H atoms was carried out using a riding model, with distances constrained to 0.82 Å for the OH group, 0.93 Å for aromatic CH, 0.98 Å for methyl CH and 0.96 Å for methyl CH3. Uiso(H) parameters were set to 1.2Ueq(carrier atom) for aromatic CH and methine CH, and 1.5Ueq(carrier atom) for OH and methyl CH3.
Schiff base compounds are often used as ligands in coordination chemistry because they are generally known for their metal binding ability, and, in particular, salicylaldimines are useful for the synthesis of transition metal complexes. Some examples include Cu, Fe and Mn complexes (Sorell, 1989; Gelling & Feringa, 1990; Dutta et al., 1997; Pyrz et al., 1991; Jacobsen, 1993). Also, N-substituted salicylaldimines are of interest because of their thermochromism and photochromism in the solid state, which may involve reversible proton transfer from the hydroxyl O atom to the imine N atom (Moustakali-Mavridis et al., 1978; Hadjoudis et al., 1987; Xu et al., 1994); charge transport occurs through intermolecular overlap of Π orbitals. Of the two tautomers, one is a phenol-imine structure and the other a keto-amine structure. Most crystal structures are of the phenol-imine tautomers (Ligtenbarg et al., 1999).
The molecular structure of title compound is shown in Fig. 1. The C1–C7, C7═N1 and C8–N1 bond lengths are 1.432 (6) Å, 1.280 (5) Å and 1.417 (5) Å, respectively, and agree with the corresponding distances in N-[3,5-bis(trifluoromethyl)phenyl]salicylaldimine [1.439 (4) Å, 1.276 (4) Å and 1.417 (4) Å; Karadayı et al., 2003]. The C2–O1 distance of 1.336 (5) Å is close to the corresponding distance in (E)-2-methoxy-6-[(2-trifluoromethylphenylimino) methyl]phenol [1.346 (4) Å, Şahin et al., 2005]. There is a strong intramolecular O–H···N hydrogen bond in (I) (Table 1), which is a common feature of phenol-imine systems. Fig. 1 also shows a strong intramolecular hydrogen bond (O1–H1···N1), which gives rise to a six-membered pseudo-ring (Bernstein et al., 1995). The O1–N1 distance of 2.618 (5) Å is comparable to those observed for analogous hydrogen bonds in 2-[2-(Hydroxymethyl)phenyliminomethyl]-phenol [2.613 (4) Å; Ersanlı et al., 2004]. The dihedral angle between the rings formed by atoms C1—C6 and C8—C13 is 2.2 (2)°. C–H···π intermolecular and π–π stacking interactions play an appreciable role in determining the conformations of organic compounds (Umezawa et al., 1999). C–H···π interactions are reported in Table 1. Also, there are two weak π—π stacking interactions, Cg(1)–Cg(2)i and Cg(2)–Cg(1)ii, with the same (symmetry related) centroid-to-centroid distance of 3.726 (3) Å [Cg(1) and Cg(2) are the centroids of rings C1–C6 and C8–C13, respectively; symmetry codes: (i): -1+X,Y,Z and (ii): 1+X,Y,Z]. These interactions result in the structure packing in layers in the [100] direction.
For related literature, see: Moustakali-Mavridis et al. (1978); Umezawa et al. (1999); Hadjoudis et al. (1987); Sorell (1989); Gelling & Feringa (1990); Dutta et al. (1997); Bernstein et al. (1995); Ersanlı et al. (2004); Jacobsen (1993); Karadayı et al. (2003); Ligtenbarg et al. (1999); Pyrz et al. (1991); Spek (1997); Xu et al. (1994); Şahin et al. (2005).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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, 1999).
C15H12NOF3 | Dx = 1.424 Mg m−3 |
Mr = 279.26 | Melting point = 361–363 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 12218 reflections |
a = 6.1462 (4) Å | θ = 2.0–28.0° |
b = 14.2873 (8) Å | µ = 0.12 mm−1 |
c = 14.8352 (13) Å | T = 296 K |
V = 1302.72 (16) Å3 | Plate, light brown |
Z = 4 | 0.64 × 0.38 × 0.10 mm |
F(000) = 576 |
Stoe IPDSII diffractometer | 1809 independent reflections |
Radiation source: sealed X-ray tube,12x0.4 mm long-fine focus | 1382 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.054 |
rotation method scans | θmax = 27.9°, θmin = 2.0° |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | h = −8→8 |
Tmin = 0.940, Tmax = 0.989 | k = −18→18 |
12218 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.076 | H-atom parameters constrained |
wR(F2) = 0.257 | w = 1/[σ2(Fo2) + (0.1762P)2 + 0.1334P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
1809 reflections | Δρmax = 0.64 e Å−3 |
183 parameters | Δρmin = −0.56 e Å−3 |
60 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.047 (18) |
C15H12NOF3 | V = 1302.72 (16) Å3 |
Mr = 279.26 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.1462 (4) Å | µ = 0.12 mm−1 |
b = 14.2873 (8) Å | T = 296 K |
c = 14.8352 (13) Å | 0.64 × 0.38 × 0.10 mm |
Stoe IPDSII diffractometer | 1809 independent reflections |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | 1382 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.989 | Rint = 0.054 |
12218 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 60 restraints |
wR(F2) = 0.257 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.64 e Å−3 |
1809 reflections | Δρmin = −0.56 e Å−3 |
183 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 | 0.2623 (7) | 0.4947 (3) | 0.5940 (3) | 0.0517 (9) | |
C2 | 0.1767 (7) | 0.5864 (3) | 0.6013 (3) | 0.0526 (9) | |
C3 | −0.0192 (8) | 0.6022 (3) | 0.6485 (3) | 0.0600 (11) | |
C4 | −0.1198 (8) | 0.5266 (3) | 0.6884 (3) | 0.0624 (11) | |
H4 | −0.2468 | 0.5367 | 0.7210 | 0.075* | |
C5 | −0.0406 (8) | 0.4364 (3) | 0.6819 (3) | 0.0619 (11) | |
H5 | −0.1142 | 0.3867 | 0.7086 | 0.074* | |
C6 | 0.1491 (8) | 0.4216 (3) | 0.6353 (3) | 0.0594 (10) | |
H6 | 0.2039 | 0.3610 | 0.6311 | 0.071* | |
C7 | 0.4560 (7) | 0.4760 (3) | 0.5434 (3) | 0.0537 (9) | |
H7 | 0.5103 | 0.4152 | 0.5427 | 0.064* | |
C8 | 0.7465 (6) | 0.5190 (3) | 0.4482 (3) | 0.0487 (8) | |
C9 | 0.8360 (7) | 0.4299 (3) | 0.4367 (3) | 0.0530 (9) | |
H9 | 0.7688 | 0.3783 | 0.4628 | 0.064* | |
C10 | 1.0232 (7) | 0.4181 (3) | 0.3868 (3) | 0.0517 (9) | |
C11 | 1.1236 (7) | 0.4940 (3) | 0.3455 (3) | 0.0573 (10) | |
H11 | 1.2494 | 0.4858 | 0.3116 | 0.069* | |
C12 | 1.0328 (8) | 0.5821 (3) | 0.3558 (3) | 0.0627 (11) | |
H12 | 1.0975 | 0.6335 | 0.3282 | 0.075* | |
C13 | 0.8490 (8) | 0.5941 (3) | 0.4062 (3) | 0.0575 (10) | |
H13 | 0.7910 | 0.6538 | 0.4126 | 0.069* | |
C14 | 1.1204 (8) | 0.3245 (3) | 0.3759 (3) | 0.0647 (11) | |
C15 | −0.1111 (10) | 0.6981 (3) | 0.6536 (4) | 0.0804 (16) | |
H15A | −0.1700 | 0.7152 | 0.5959 | 0.121* | |
H15B | 0.0016 | 0.7414 | 0.6699 | 0.121* | |
H15C | −0.2244 | 0.6998 | 0.6981 | 0.121* | |
F1A | 1.3306 (15) | 0.3212 (7) | 0.3954 (7) | 0.0894 (11) | 0.494 (8) |
F2A | 1.1093 (16) | 0.2935 (5) | 0.2898 (6) | 0.0894 (11) | 0.494 (8) |
F3A | 1.0319 (15) | 0.2600 (5) | 0.4290 (6) | 0.0894 (11) | 0.494 (8) |
F1B | 1.3337 (15) | 0.3227 (7) | 0.3589 (7) | 0.0894 (11) | 0.506 (8) |
F2B | 1.0222 (15) | 0.2705 (5) | 0.3169 (6) | 0.0894 (11) | 0.506 (8) |
F3B | 1.1159 (15) | 0.2748 (5) | 0.4569 (5) | 0.0894 (11) | 0.506 (8) |
N1 | 0.5574 (6) | 0.5394 (2) | 0.4993 (2) | 0.0535 (8) | |
O1 | 0.2753 (5) | 0.6596 (2) | 0.5630 (3) | 0.0673 (10) | |
H1 | 0.3906 | 0.6426 | 0.5405 | 0.101* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0514 (18) | 0.0513 (18) | 0.052 (2) | −0.0010 (16) | −0.0029 (18) | −0.0039 (15) |
C2 | 0.0508 (19) | 0.0510 (19) | 0.056 (2) | 0.0015 (16) | 0.0000 (18) | 0.0016 (16) |
C3 | 0.059 (2) | 0.063 (2) | 0.059 (2) | 0.0042 (19) | −0.002 (2) | −0.0033 (18) |
C4 | 0.054 (2) | 0.079 (3) | 0.054 (2) | −0.001 (2) | 0.005 (2) | 0.002 (2) |
C5 | 0.064 (2) | 0.064 (2) | 0.057 (2) | −0.011 (2) | 0.005 (2) | 0.0021 (19) |
C6 | 0.063 (2) | 0.054 (2) | 0.061 (2) | −0.0007 (19) | 0.002 (2) | 0.0024 (18) |
C7 | 0.0536 (19) | 0.0514 (18) | 0.056 (2) | 0.0008 (17) | 0.0018 (18) | −0.0022 (16) |
C8 | 0.0451 (16) | 0.0493 (18) | 0.0518 (19) | −0.0039 (16) | −0.0025 (17) | 0.0029 (15) |
C9 | 0.0489 (19) | 0.0518 (19) | 0.058 (2) | −0.0040 (17) | 0.0042 (18) | 0.0064 (17) |
C10 | 0.0499 (19) | 0.0541 (19) | 0.0512 (19) | −0.0034 (17) | 0.0004 (17) | 0.0008 (16) |
C11 | 0.053 (2) | 0.062 (2) | 0.057 (2) | −0.0048 (19) | 0.0074 (18) | 0.0025 (18) |
C12 | 0.069 (3) | 0.055 (2) | 0.064 (2) | −0.011 (2) | 0.006 (2) | 0.0072 (19) |
C13 | 0.061 (2) | 0.0479 (18) | 0.063 (2) | −0.0026 (18) | −0.002 (2) | 0.0035 (17) |
C14 | 0.062 (2) | 0.064 (2) | 0.068 (3) | −0.001 (2) | 0.011 (2) | −0.003 (2) |
C15 | 0.076 (3) | 0.062 (3) | 0.103 (4) | 0.014 (2) | 0.023 (3) | 0.000 (3) |
F1A | 0.094 (2) | 0.0753 (15) | 0.099 (3) | 0.0152 (14) | 0.003 (2) | −0.0061 (17) |
F2A | 0.094 (2) | 0.0753 (15) | 0.099 (3) | 0.0152 (14) | 0.003 (2) | −0.0061 (17) |
F3A | 0.094 (2) | 0.0753 (15) | 0.099 (3) | 0.0152 (14) | 0.003 (2) | −0.0061 (17) |
F1B | 0.094 (2) | 0.0753 (15) | 0.099 (3) | 0.0152 (14) | 0.003 (2) | −0.0061 (17) |
F2B | 0.094 (2) | 0.0753 (15) | 0.099 (3) | 0.0152 (14) | 0.003 (2) | −0.0061 (17) |
F3B | 0.094 (2) | 0.0753 (15) | 0.099 (3) | 0.0152 (14) | 0.003 (2) | −0.0061 (17) |
N1 | 0.0489 (16) | 0.0511 (16) | 0.0605 (19) | 0.0011 (14) | −0.0017 (15) | 0.0037 (14) |
O1 | 0.0653 (19) | 0.0497 (15) | 0.087 (2) | 0.0024 (14) | 0.0152 (18) | 0.0053 (14) |
C1—C6 | 1.397 (6) | C9—H9 | 0.9300 |
C1—C2 | 1.416 (5) | C10—C11 | 1.390 (6) |
C1—C7 | 1.432 (6) | C10—C14 | 1.473 (6) |
C2—O1 | 1.335 (5) | C11—C12 | 1.386 (6) |
C2—C3 | 1.411 (6) | C11—H11 | 0.9300 |
C3—C4 | 1.378 (6) | C12—C13 | 1.365 (7) |
C3—C15 | 1.484 (6) | C12—H12 | 0.9300 |
C4—C5 | 1.381 (7) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—F2B | 1.312 (9) |
C5—C6 | 1.372 (6) | C14—F1A | 1.325 (10) |
C5—H5 | 0.9300 | C14—F3A | 1.329 (9) |
C6—H6 | 0.9300 | C14—F1B | 1.336 (10) |
C7—N1 | 1.280 (5) | C14—F2A | 1.354 (9) |
C7—H7 | 0.9300 | C14—F3B | 1.396 (9) |
C8—C13 | 1.392 (5) | C15—H15A | 0.9600 |
C8—C9 | 1.397 (6) | C15—H15B | 0.9600 |
C8—N1 | 1.417 (5) | C15—H15C | 0.9600 |
C9—C10 | 1.378 (6) | O1—H1 | 0.8200 |
C6—C1—C2 | 118.3 (4) | C13—C12—C11 | 120.5 (4) |
C6—C1—C7 | 120.3 (4) | C13—C12—H12 | 119.7 |
C2—C1—C7 | 121.4 (4) | C11—C12—H12 | 119.7 |
O1—C2—C3 | 118.3 (4) | C12—C13—C8 | 121.5 (4) |
O1—C2—C1 | 121.6 (4) | C12—C13—H13 | 119.2 |
C3—C2—C1 | 120.2 (4) | C8—C13—H13 | 119.2 |
C4—C3—C2 | 118.1 (4) | F2B—C14—F1A | 125.0 (7) |
C4—C3—C15 | 122.1 (4) | F2B—C14—F3A | 78.4 (6) |
C2—C3—C15 | 119.8 (4) | F1A—C14—F3A | 104.2 (7) |
C3—C4—C5 | 122.9 (4) | F2B—C14—F1B | 108.3 (7) |
C3—C4—H4 | 118.5 | F3A—C14—F1B | 120.0 (7) |
C5—C4—H4 | 118.5 | F1A—C14—F2A | 104.1 (6) |
C6—C5—C4 | 118.6 (4) | F3A—C14—F2A | 108.2 (6) |
C6—C5—H5 | 120.7 | F1B—C14—F2A | 82.2 (6) |
C4—C5—H5 | 120.7 | F2B—C14—F3B | 105.4 (6) |
C5—C6—C1 | 121.9 (4) | F1A—C14—F3B | 79.2 (6) |
C5—C6—H6 | 119.0 | F1B—C14—F3B | 99.9 (7) |
C1—C6—H6 | 119.0 | F2A—C14—F3B | 130.2 (6) |
N1—C7—C1 | 122.7 (4) | F2B—C14—C10 | 114.8 (5) |
N1—C7—H7 | 118.6 | F1A—C14—C10 | 113.8 (6) |
C1—C7—H7 | 118.6 | F3A—C14—C10 | 113.5 (5) |
C13—C8—C9 | 118.0 (4) | F1B—C14—C10 | 115.9 (6) |
C13—C8—N1 | 116.9 (3) | F2A—C14—C10 | 112.4 (5) |
C9—C8—N1 | 125.1 (3) | F3B—C14—C10 | 111.0 (5) |
C10—C9—C8 | 120.4 (4) | C3—C15—H15A | 109.5 |
C10—C9—H9 | 119.8 | C3—C15—H15B | 109.5 |
C8—C9—H9 | 119.8 | H15A—C15—H15B | 109.5 |
C9—C10—C11 | 120.8 (4) | C3—C15—H15C | 109.5 |
C9—C10—C14 | 120.6 (4) | H15A—C15—H15C | 109.5 |
C11—C10—C14 | 118.6 (4) | H15B—C15—H15C | 109.5 |
C12—C11—C10 | 118.8 (4) | C7—N1—C8 | 121.9 (3) |
C12—C11—H11 | 120.6 | C2—O1—H1 | 109.5 |
C10—C11—H11 | 120.6 | ||
C6—C1—C2—O1 | −179.5 (4) | C14—C10—C11—C12 | −179.9 (4) |
C7—C1—C2—O1 | −1.5 (6) | C10—C11—C12—C13 | 0.5 (7) |
C6—C1—C2—C3 | −0.6 (6) | C11—C12—C13—C8 | −0.3 (7) |
C7—C1—C2—C3 | 177.5 (4) | C9—C8—C13—C12 | −0.7 (6) |
O1—C2—C3—C4 | −179.6 (4) | N1—C8—C13—C12 | 179.7 (4) |
C1—C2—C3—C4 | 1.4 (6) | C9—C10—C14—F2B | 77.6 (7) |
O1—C2—C3—C15 | 0.8 (6) | C11—C10—C14—F2B | −102.1 (7) |
C1—C2—C3—C15 | −178.2 (5) | C9—C10—C14—F1A | −129.0 (6) |
C2—C3—C4—C5 | −1.7 (7) | C11—C10—C14—F1A | 51.3 (8) |
C15—C3—C4—C5 | 177.8 (5) | C9—C10—C14—F3A | −10.1 (8) |
C3—C4—C5—C6 | 1.3 (7) | C11—C10—C14—F3A | 170.2 (6) |
C4—C5—C6—C1 | −0.4 (7) | C9—C10—C14—F1B | −154.9 (6) |
C2—C1—C6—C5 | 0.1 (6) | C11—C10—C14—F1B | 25.4 (8) |
C7—C1—C6—C5 | −178.0 (4) | C9—C10—C14—F2A | 113.0 (6) |
C6—C1—C7—N1 | 175.1 (4) | C11—C10—C14—F2A | −66.7 (7) |
C2—C1—C7—N1 | −2.9 (6) | C9—C10—C14—F3B | −41.9 (7) |
C13—C8—C9—C10 | 1.6 (6) | C11—C10—C14—F3B | 138.4 (6) |
N1—C8—C9—C10 | −178.8 (4) | C1—C7—N1—C8 | −178.7 (3) |
C8—C9—C10—C11 | −1.5 (6) | C13—C8—N1—C7 | −177.2 (4) |
C8—C9—C10—C14 | 178.8 (4) | C9—C8—N1—C7 | 3.2 (6) |
C9—C10—C11—C12 | 0.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.90 | 2.618 (5) | 146 |
C4—H4···Cg2i | 0.93 | 2.91 | 3.667 (5) | 140 |
C11—H11···Cg1ii | 0.93 | 2.76 | 3.571 (5) | 146 |
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+3/2, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H12NOF3 |
Mr | 279.26 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 6.1462 (4), 14.2873 (8), 14.8352 (13) |
V (Å3) | 1302.72 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.64 × 0.38 × 0.10 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Integration (X-RED; Stoe & Cie, 2002) |
Tmin, Tmax | 0.940, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12218, 1809, 1382 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.076, 0.257, 1.13 |
No. of reflections | 1809 |
No. of parameters | 183 |
No. of restraints | 60 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.56 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.90 | 2.618 (5) | 145.9 |
C4—H4···Cg2i | 0.93 | 2.91 | 3.667 (5) | 140 |
C11—H11···Cg1ii | 0.93 | 2.76 | 3.571 (5) | 146 |
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+3/2, −y+1, z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Schiff base compounds are often used as ligands in coordination chemistry because they are generally known for their metal binding ability, and, in particular, salicylaldimines are useful for the synthesis of transition metal complexes. Some examples include Cu, Fe and Mn complexes (Sorell, 1989; Gelling & Feringa, 1990; Dutta et al., 1997; Pyrz et al., 1991; Jacobsen, 1993). Also, N-substituted salicylaldimines are of interest because of their thermochromism and photochromism in the solid state, which may involve reversible proton transfer from the hydroxyl O atom to the imine N atom (Moustakali-Mavridis et al., 1978; Hadjoudis et al., 1987; Xu et al., 1994); charge transport occurs through intermolecular overlap of Π orbitals. Of the two tautomers, one is a phenol-imine structure and the other a keto-amine structure. Most crystal structures are of the phenol-imine tautomers (Ligtenbarg et al., 1999).
The molecular structure of title compound is shown in Fig. 1. The C1–C7, C7═N1 and C8–N1 bond lengths are 1.432 (6) Å, 1.280 (5) Å and 1.417 (5) Å, respectively, and agree with the corresponding distances in N-[3,5-bis(trifluoromethyl)phenyl]salicylaldimine [1.439 (4) Å, 1.276 (4) Å and 1.417 (4) Å; Karadayı et al., 2003]. The C2–O1 distance of 1.336 (5) Å is close to the corresponding distance in (E)-2-methoxy-6-[(2-trifluoromethylphenylimino) methyl]phenol [1.346 (4) Å, Şahin et al., 2005]. There is a strong intramolecular O–H···N hydrogen bond in (I) (Table 1), which is a common feature of phenol-imine systems. Fig. 1 also shows a strong intramolecular hydrogen bond (O1–H1···N1), which gives rise to a six-membered pseudo-ring (Bernstein et al., 1995). The O1–N1 distance of 2.618 (5) Å is comparable to those observed for analogous hydrogen bonds in 2-[2-(Hydroxymethyl)phenyliminomethyl]-phenol [2.613 (4) Å; Ersanlı et al., 2004]. The dihedral angle between the rings formed by atoms C1—C6 and C8—C13 is 2.2 (2)°. C–H···π intermolecular and π–π stacking interactions play an appreciable role in determining the conformations of organic compounds (Umezawa et al., 1999). C–H···π interactions are reported in Table 1. Also, there are two weak π—π stacking interactions, Cg(1)–Cg(2)i and Cg(2)–Cg(1)ii, with the same (symmetry related) centroid-to-centroid distance of 3.726 (3) Å [Cg(1) and Cg(2) are the centroids of rings C1–C6 and C8–C13, respectively; symmetry codes: (i): -1+X,Y,Z and (ii): 1+X,Y,Z]. These interactions result in the structure packing in layers in the [100] direction.