Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803000722/ob6204sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803000722/ob6204Isup2.hkl |
CCDC reference: 204690
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.005 Å
- R factor = 0.063
- wR factor = 0.191
- Data-to-parameter ratio = 9.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
SHFSU_01 Alert C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.062 Additional refinement cycles may be required. PLAT_213 Alert C Atom F4B has ADP max/min Ratio ........... 3.20 prolate
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
An ethanol solution of 3,5-bis(trifluoromethyl)aminobenzene (2.29 g/20 ml e thanol) was added dropwise at room temperature to a solution of salicylaldehyde (1.22 g, 0.01 mol) in ethanol (20 ml) and large amounts of a yellow precipitate were formed. The mixture was stirred for 30 min at this temperature and filtered under vacuum. Spectroscopically pure (I) was obtained by crystallization from toluene as pale-yellow needles (yield: 93%, m.p.: 369–371 K); elemental analysis, calculated for C15H9F6N: C 54.05, H 2.70, N 4.20%; found: C 54.34, H 2.78, N 4.19%. 1H NMR (CDCl3, 400 MHz): δ 6.9–7.1 (m, 7H, Ar—H), 8.5 (s, 1H, H—C═N), 12.2 (s, 1H, OH). IR (KBr) 3600–3300 (br, Ph—OH), 2950 (H—CN), 1650 (C═N), 1600 (Ar—CH). Uv–vis (CHCl3): λ = 240 (ε: 2000), 276 (max., ε: 2927), 346 nm (ε: 1835).
The disordered trifluoromethyl F atoms were refined anisotropically using ADP with distance and angle restraints in two positions.
Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997).
C15H9F6NO | F(000) = 672 |
Mr = 333.23 | Dx = 1.586 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yab | Cell parameters from 35 reflections |
a = 7.509 (1) Å | θ = 5–25° |
b = 26.634 (2) Å | µ = 0.16 mm−1 |
c = 7.854 (1) Å | T = 180 K |
β = 117.34 (1)° | Plate, yellow |
V = 1395.3 (3) Å3 | 0.3 × 0.3 × 0.02 mm |
Z = 4 |
Siemens P4 diffractometer | Rint = 0.068 |
Radiation source: fine-focus sealed tube | θmax = 25.2°, θmin = 3.4° |
Graphite monochromator | h = −4→9 |
ω scans | k = −30→31 |
9212 measured reflections | l = −9→9 |
2508 independent reflections | 1 standard reflections every 120 min |
1400 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.0908P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.062 |
2508 reflections | Δρmax = 0.22 e Å−3 |
264 parameters | Δρmin = −0.23 e Å−3 |
346 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (3) |
C15H9F6NO | V = 1395.3 (3) Å3 |
Mr = 333.23 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 7.509 (1) Å | µ = 0.16 mm−1 |
b = 26.634 (2) Å | T = 180 K |
c = 7.854 (1) Å | 0.3 × 0.3 × 0.02 mm |
β = 117.34 (1)° |
Siemens P4 diffractometer | Rint = 0.068 |
9212 measured reflections | 1 standard reflections every 120 min |
2508 independent reflections | intensity decay: none |
1400 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.063 | 346 restraints |
wR(F2) = 0.191 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.22 e Å−3 |
2508 reflections | Δρmin = −0.23 e Å−3 |
264 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. The structure was solved by direct methods and refined using full-matrix least squares with all non-H atoms anisotropic. 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) | |
C12 | 0.2074 (4) | 0.90153 (12) | 0.1261 (5) | 0.0490 (8) | |
C14 | −0.0075 (6) | 0.91051 (14) | −0.0061 (6) | 0.0642 (10) | |
F1A | −0.1096 (9) | 0.8692 (2) | −0.0784 (14) | 0.116 (4) | 0.639 (14) |
F2A | −0.0984 (9) | 0.9350 (5) | 0.0669 (11) | 0.138 (5) | 0.639 (14) |
F3A | −0.0283 (8) | 0.9355 (4) | −0.1585 (10) | 0.132 (4) | 0.639 (14) |
F1B | −0.0707 (16) | 0.8904 (7) | −0.1714 (14) | 0.109 (6) | 0.361 (14) |
F2B | −0.1287 (11) | 0.8926 (6) | 0.0629 (18) | 0.102 (5) | 0.361 (14) |
F3B | −0.0635 (14) | 0.9572 (3) | −0.035 (3) | 0.103 (6) | 0.361 (14) |
C10 | 0.5439 (5) | 0.93086 (12) | 0.2953 (5) | 0.0501 (9) | |
C15 | 0.6928 (5) | 0.97260 (14) | 0.3501 (6) | 0.0623 (10) | |
F4A | 0.8756 (8) | 0.9567 (3) | 0.4029 (13) | 0.096 (2) | 0.639 (14) |
F5A | 0.7045 (13) | 0.9985 (4) | 0.4971 (9) | 0.089 (2) | 0.639 (14) |
F6A | 0.6681 (17) | 1.0013 (5) | 0.2131 (15) | 0.144 (5) | 0.639 (14) |
F4B | 0.8762 (16) | 0.9587 (6) | 0.451 (3) | 0.149 (7) | 0.361 (14) |
F5B | 0.637 (4) | 1.0118 (7) | 0.410 (4) | 0.166 (7) | 0.361 (14) |
F6B | 0.6673 (18) | 0.9991 (7) | 0.193 (2) | 0.087 (5) | 0.361 (14) |
O1 | 0.4776 (3) | 0.69821 (9) | 0.3629 (4) | 0.0642 (7) | |
H1 | 0.4496 | 0.7277 | 0.3320 | 0.096* | |
N1 | 0.5228 (4) | 0.79528 (10) | 0.3935 (4) | 0.0493 (7) | |
C1 | 0.9071 (5) | 0.73333 (14) | 0.8136 (5) | 0.0562 (9) | |
H1A | 0.9718 | 0.7618 | 0.8826 | 0.067* | |
C2 | 0.9792 (6) | 0.68696 (15) | 0.8896 (6) | 0.0657 (11) | |
H2 | 1.0923 | 0.6840 | 1.0078 | 0.079* | |
C3 | 0.8803 (6) | 0.64458 (16) | 0.7871 (6) | 0.0678 (11) | |
H3 | 0.9279 | 0.6129 | 0.8377 | 0.081* | |
C4 | 0.7136 (5) | 0.64847 (14) | 0.6129 (6) | 0.0635 (10) | |
H4 | 0.6480 | 0.6197 | 0.5464 | 0.076* | |
C5 | 0.6433 (5) | 0.69580 (13) | 0.5362 (5) | 0.0527 (9) | |
C6 | 0.7410 (5) | 0.73888 (12) | 0.6373 (5) | 0.0481 (8) | |
C7 | 0.6716 (5) | 0.78797 (13) | 0.5579 (5) | 0.0503 (9) | |
H7 | 0.7386 | 0.8158 | 0.6303 | 0.060* | |
C8 | 0.4697 (5) | 0.84496 (12) | 0.3242 (4) | 0.0462 (8) | |
C9 | 0.6062 (4) | 0.88344 (12) | 0.3683 (5) | 0.0497 (9) | |
H9 | 0.7414 | 0.8774 | 0.4480 | 0.060* | |
C11 | 0.3427 (5) | 0.94034 (13) | 0.1737 (5) | 0.0531 (9) | |
H11 | 0.3003 | 0.9724 | 0.1253 | 0.064* | |
C13 | 0.2691 (4) | 0.85405 (13) | 0.1997 (5) | 0.0494 (9) | |
H13 | 0.1763 | 0.8281 | 0.1660 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C12 | 0.0446 (18) | 0.053 (2) | 0.0483 (19) | −0.0005 (16) | 0.0202 (16) | −0.0031 (16) |
C14 | 0.058 (2) | 0.059 (2) | 0.065 (2) | −0.0027 (19) | 0.019 (2) | −0.004 (2) |
F1A | 0.060 (3) | 0.080 (4) | 0.140 (8) | −0.013 (2) | −0.013 (4) | −0.025 (4) |
F2A | 0.071 (4) | 0.206 (12) | 0.119 (6) | 0.044 (7) | 0.027 (3) | −0.061 (7) |
F3A | 0.070 (3) | 0.193 (10) | 0.099 (5) | 0.003 (4) | 0.010 (3) | 0.067 (6) |
F1B | 0.081 (7) | 0.134 (14) | 0.072 (6) | 0.012 (8) | 0.002 (5) | −0.041 (7) |
F2B | 0.046 (4) | 0.122 (11) | 0.125 (9) | −0.004 (6) | 0.029 (5) | 0.025 (8) |
F3B | 0.062 (5) | 0.057 (5) | 0.158 (14) | 0.021 (3) | 0.023 (7) | 0.003 (5) |
C10 | 0.0493 (19) | 0.050 (2) | 0.0485 (19) | −0.0072 (16) | 0.0201 (16) | −0.0030 (16) |
C15 | 0.065 (2) | 0.048 (2) | 0.068 (2) | −0.0061 (18) | 0.025 (2) | 0.0044 (19) |
F4A | 0.059 (3) | 0.077 (4) | 0.174 (6) | −0.024 (3) | 0.073 (4) | −0.038 (4) |
F5A | 0.090 (4) | 0.090 (5) | 0.097 (4) | −0.046 (3) | 0.053 (3) | −0.053 (3) |
F6A | 0.172 (8) | 0.115 (8) | 0.094 (5) | −0.089 (5) | 0.017 (5) | 0.016 (5) |
F4B | 0.086 (7) | 0.090 (9) | 0.145 (9) | −0.040 (5) | −0.055 (7) | 0.071 (7) |
F5B | 0.211 (17) | 0.107 (11) | 0.278 (19) | −0.093 (9) | 0.197 (16) | −0.109 (14) |
F6B | 0.055 (6) | 0.107 (12) | 0.097 (9) | −0.003 (7) | 0.032 (6) | 0.048 (8) |
O1 | 0.0539 (15) | 0.0540 (15) | 0.0853 (18) | −0.0043 (11) | 0.0326 (14) | −0.0109 (13) |
N1 | 0.0473 (16) | 0.0478 (17) | 0.0591 (18) | 0.0004 (12) | 0.0300 (15) | 0.0010 (14) |
C1 | 0.058 (2) | 0.062 (2) | 0.054 (2) | 0.0021 (17) | 0.0300 (18) | 0.0056 (18) |
C2 | 0.065 (2) | 0.077 (3) | 0.065 (2) | 0.007 (2) | 0.038 (2) | 0.016 (2) |
C3 | 0.071 (2) | 0.063 (3) | 0.086 (3) | 0.015 (2) | 0.050 (2) | 0.023 (2) |
C4 | 0.064 (2) | 0.049 (2) | 0.092 (3) | −0.0026 (18) | 0.048 (2) | 0.006 (2) |
C5 | 0.0420 (18) | 0.056 (2) | 0.068 (2) | −0.0014 (16) | 0.0323 (19) | 0.0015 (19) |
C6 | 0.0514 (19) | 0.045 (2) | 0.060 (2) | 0.0015 (15) | 0.0361 (17) | 0.0002 (16) |
C7 | 0.0496 (19) | 0.054 (2) | 0.056 (2) | −0.0053 (16) | 0.0317 (18) | −0.0051 (17) |
C8 | 0.0470 (18) | 0.0478 (19) | 0.0478 (18) | −0.0036 (15) | 0.0250 (16) | −0.0054 (15) |
C9 | 0.0403 (17) | 0.055 (2) | 0.0520 (19) | −0.0026 (15) | 0.0199 (15) | −0.0017 (17) |
C11 | 0.060 (2) | 0.048 (2) | 0.0524 (19) | 0.0018 (16) | 0.0267 (18) | 0.0000 (16) |
C13 | 0.0465 (19) | 0.050 (2) | 0.0543 (19) | −0.0090 (15) | 0.0249 (17) | −0.0093 (17) |
C12—C11 | 1.375 (4) | N1—C7 | 1.276 (4) |
C12—C13 | 1.379 (5) | N1—C8 | 1.417 (4) |
C12—C14 | 1.483 (5) | C1—C2 | 1.370 (5) |
C14—F2A | 1.257 (6) | C1—C6 | 1.381 (4) |
C14—F1B | 1.277 (8) | C1—H1A | 0.9300 |
C14—F3B | 1.299 (7) | C2—C3 | 1.387 (5) |
C14—F1A | 1.312 (6) | C2—H2 | 0.9300 |
C14—F3A | 1.315 (6) | C3—C4 | 1.370 (5) |
C14—F2B | 1.343 (8) | C3—H3 | 0.9300 |
C10—C9 | 1.377 (4) | C4—C5 | 1.392 (5) |
C10—C11 | 1.391 (4) | C4—H4 | 0.9300 |
C10—C15 | 1.493 (5) | C5—C6 | 1.397 (5) |
C15—F6A | 1.262 (8) | C6—C7 | 1.439 (4) |
C15—F4B | 1.289 (10) | C7—H7 | 0.9300 |
C15—F5B | 1.294 (11) | C8—C9 | 1.377 (4) |
C15—F4A | 1.309 (6) | C8—C13 | 1.389 (4) |
C15—F5A | 1.313 (7) | C9—H9 | 0.9300 |
C15—F6B | 1.355 (10) | C11—H11 | 0.9300 |
O1—C5 | 1.360 (4) | C13—H13 | 0.9300 |
O1—H1 | 0.8200 | ||
C11—C12—C13 | 120.7 (3) | C2—C1—H1A | 119.1 |
C11—C12—C14 | 120.0 (3) | C6—C1—H1A | 119.1 |
C13—C12—C14 | 119.3 (3) | C1—C2—C3 | 118.8 (4) |
F1B—C14—F3B | 106.5 (9) | C1—C2—H2 | 120.6 |
F2A—C14—F1A | 107.5 (6) | C3—C2—H2 | 120.6 |
F2A—C14—F3A | 106.8 (7) | C4—C3—C2 | 121.2 (4) |
F1A—C14—F3A | 103.3 (6) | C4—C3—H3 | 119.4 |
F1B—C14—F2B | 104.9 (9) | C2—C3—H3 | 119.4 |
F3B—C14—F2B | 100.7 (8) | C3—C4—C5 | 119.5 (4) |
F2A—C14—C12 | 114.1 (4) | C3—C4—H4 | 120.3 |
F1B—C14—C12 | 114.9 (6) | C5—C4—H4 | 120.3 |
F3B—C14—C12 | 115.9 (5) | O1—C5—C4 | 117.8 (3) |
F1A—C14—C12 | 113.6 (4) | O1—C5—C6 | 122.0 (3) |
F3A—C14—C12 | 110.8 (4) | C4—C5—C6 | 120.1 (3) |
F2B—C14—C12 | 112.4 (5) | C1—C6—C5 | 118.6 (3) |
C9—C10—C11 | 120.5 (3) | C1—C6—C7 | 120.8 (3) |
C9—C10—C15 | 119.8 (3) | C5—C6—C7 | 120.6 (3) |
C11—C10—C15 | 119.7 (3) | N1—C7—C6 | 123.5 (3) |
F4B—C15—F5B | 116.3 (13) | N1—C7—H7 | 118.3 |
F6A—C15—F4A | 100.8 (8) | C6—C7—H7 | 118.3 |
F6A—C15—F5A | 110.8 (8) | C9—C8—C13 | 119.3 (3) |
F4A—C15—F5A | 104.7 (5) | C9—C8—N1 | 123.6 (3) |
F4B—C15—F6B | 112.0 (10) | C13—C8—N1 | 117.1 (3) |
F5B—C15—F6B | 88.8 (15) | C8—C9—C10 | 120.4 (3) |
F6A—C15—C10 | 114.0 (6) | C8—C9—H9 | 119.8 |
F4B—C15—C10 | 114.2 (7) | C10—C9—H9 | 119.8 |
F5B—C15—C10 | 112.3 (10) | C12—C11—C10 | 119.0 (3) |
F4A—C15—C10 | 112.9 (4) | C12—C11—H11 | 120.5 |
F5A—C15—C10 | 112.6 (6) | C10—C11—H11 | 120.5 |
F6B—C15—C10 | 110.5 (8) | C12—C13—C8 | 120.1 (3) |
C5—O1—H1 | 109.5 | C12—C13—H13 | 119.9 |
C7—N1—C8 | 119.5 (3) | C8—C13—H13 | 119.9 |
C2—C1—C6 | 121.8 (4) | ||
C11—C12—C14—F2A | −73.1 (9) | C2—C3—C4—C5 | 0.7 (5) |
C13—C12—C14—F2A | 107.0 (8) | C3—C4—C5—O1 | 179.9 (3) |
C11—C12—C14—F1B | 109.6 (11) | C3—C4—C5—C6 | −0.6 (5) |
C13—C12—C14—F1B | −70.2 (11) | C2—C1—C6—C5 | 0.9 (5) |
C11—C12—C14—F3B | −15.4 (12) | C2—C1—C6—C7 | −178.2 (3) |
C13—C12—C14—F3B | 164.7 (11) | O1—C5—C6—C1 | 179.3 (3) |
C11—C12—C14—F1A | 163.2 (7) | C4—C5—C6—C1 | −0.1 (5) |
C13—C12—C14—F1A | −16.7 (8) | O1—C5—C6—C7 | −1.6 (5) |
C11—C12—C14—F3A | 47.5 (8) | C4—C5—C6—C7 | 179.0 (3) |
C13—C12—C14—F3A | −132.3 (7) | C8—N1—C7—C6 | −177.7 (3) |
C11—C12—C14—F2B | −130.5 (9) | C1—C6—C7—N1 | 177.8 (3) |
C13—C12—C14—F2B | 49.6 (9) | C5—C6—C7—N1 | −1.3 (5) |
C9—C10—C15—F6A | 138.9 (9) | C7—N1—C8—C9 | 31.6 (5) |
C11—C10—C15—F6A | −42.4 (9) | C7—N1—C8—C13 | −150.8 (3) |
C9—C10—C15—F4B | 6.3 (12) | C13—C8—C9—C10 | 2.2 (5) |
C11—C10—C15—F4B | −174.9 (11) | N1—C8—C9—C10 | 179.8 (3) |
C9—C10—C15—F5B | −128.9 (15) | C11—C10—C9—C8 | −0.9 (5) |
C11—C10—C15—F5B | 49.9 (16) | C15—C10—C9—C8 | 177.8 (3) |
C9—C10—C15—F4A | 24.6 (6) | C13—C12—C11—C10 | 1.0 (5) |
C11—C10—C15—F4A | −156.6 (5) | C14—C12—C11—C10 | −178.9 (3) |
C9—C10—C15—F5A | −93.7 (6) | C9—C10—C11—C12 | −0.6 (5) |
C11—C10—C15—F5A | 85.0 (6) | C15—C10—C11—C12 | −179.4 (3) |
C9—C10—C15—F6B | 133.7 (8) | C11—C12—C13—C8 | 0.3 (5) |
C11—C10—C15—F6B | −47.6 (8) | C14—C12—C13—C8 | −179.8 (3) |
C6—C1—C2—C3 | −0.9 (5) | C9—C8—C13—C12 | −1.9 (5) |
C1—C2—C3—C4 | 0.1 (5) | N1—C8—C13—C12 | −179.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.88 | 2.604 (4) | 147 |
C7—H7···F1Ai | 0.93 | 2.48 | 3.351 (8) | 156 |
Symmetry code: (i) x+1, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H9F6NO |
Mr | 333.23 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 180 |
a, b, c (Å) | 7.509 (1), 26.634 (2), 7.854 (1) |
β (°) | 117.34 (1) |
V (Å3) | 1395.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.3 × 0.3 × 0.02 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9212, 2508, 1400 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.191, 1.06 |
No. of reflections | 2508 |
No. of parameters | 264 |
No. of restraints | 346 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.23 |
Computer programs: XSCANS (Siemens, 1991), XSCANS, SHELXTL (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997).
C12—C11 | 1.375 (4) | N1—C8 | 1.417 (4) |
C12—C13 | 1.379 (5) | C1—C6 | 1.381 (4) |
O1—C5 | 1.360 (4) | C6—C7 | 1.439 (4) |
N1—C7 | 1.276 (4) | C8—C9 | 1.377 (4) |
C11—C12—C13 | 120.7 (3) | C1—C6—C7 | 120.8 (3) |
C11—C12—C14 | 120.0 (3) | C5—C6—C7 | 120.6 (3) |
C13—C12—C14 | 119.3 (3) | N1—C7—C6 | 123.5 (3) |
C7—N1—C8 | 119.5 (3) | C9—C8—N1 | 123.6 (3) |
O1—C5—C4 | 117.8 (3) | C13—C8—N1 | 117.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.88 | 2.604 (4) | 147 |
C7—H7···F1Ai | 0.93 | 2.48 | 3.351 (8) | 156 |
Symmetry code: (i) x+1, y, z+1. |
Solvent extraction is now widely accepted as a process for the recovery of metal ions from aqueus solution in hydrometallurgical and environmental application (El Aamrani et al., 1999) with new interest in the processing of heavy metals by chelation incorporated with supercritical fluid (SCF) extraction processing. We have designed novel Shiff base type chelating agents by attaching CO2-philic fluoroalkyl groups, and synthesized and characterized these compounds for supercritical CO2 extraction of heavy metals. In this study, we report the structure of the title compound, (I).
The molecule structure of (I) is shown in Fig. 1. The C8—N1 and C7—C6 bond lengths are 1.417 (4) and 1.439 (4) Å, respectively (Table 1), and agree with the corresponding distances in 2-[(4-hydroxyphenyl)iminomethyl]thiophene [1.422 (2) and 1.447 (3) Å; Kazak et al., 2000] and trans-[4-dimethylaminophenyl)iminomethyl]-N-methylpyridinium para-toluenesulfonate [1.413 (3) and 1.461 Å; Coe et al., 2001]. The N1═C7 bond length of 1.276 (4) Å is typical of a double bond, which is similar to the corresponding bond lenghts in N-(2,4-dinitrophenyl)-N-methylhydrazone [1.279 (2) Å; Aygün et al., 1998], 2-salicylideneamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrite [1.281 (2) Å; Elerman & Elmalı, 1998] and 2-[(4-hydroxyphenyl)iminomethyl]thiophene [1.282 (2) Å; Kazak et al., 2000]. The O1—C5 distance of 1.360 (4) Å is nearly equal to the value of 1.349 (6) Å in 3-tert-butyl-2-hydroxy-5-methoxyazobenzene (Işık et al., 1998). The two aromatic rings have different orientations and the dihedral angle between the rings formed by atoms C1–C6 and C8–C13 is 29.57 (2)°.
There is an intramolecular O1—H1···N1 hydrogen bond and an intermolecular C7—H7···F1A hydrogen bond (Table 2). Both CF3 groups showed rotational disorder.