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organic compounds
In the molecule of the title Schiff base, C19H22FN, the fluorine-bearing aromatic ring makes an angle of 68.0 (1)° with the other sterically crowded aromatic ring.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008263/bt6629sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008263/bt6629Isup2.hkl |
CCDC reference: 270246
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.195
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 - C1 .. 5.17 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
N-(2-Fluorobenzylidene)-2,6-diisopropylbenzenamine top
Crystal data top
C19H22FN | Z = 2 |
Mr = 283.38 | F(000) = 304 |
Triclinic, P1 | Dx = 1.136 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.265 (1) Å | Cell parameters from 982 reflections |
b = 10.510 (1) Å | θ = 2.1–27.1° |
c = 10.841 (1) Å | µ = 0.07 mm−1 |
α = 113.855 (2)° | T = 295 K |
β = 98.767 (2)° | Block, yellow |
γ = 98.390 (2)° | 0.50 × 0.42 × 0.22 mm |
V = 828.5 (2) Å3 |
Data collection top
Bruker SMART area-detector diffractometer | 2421 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 27.2°, θmin = 2.1° |
φ and ω scans | h = −10→10 |
7091 measured reflections | k = −13→13 |
3581 independent reflections | l = −13→13 |
Refinement top
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1003P)2 + 0.1118P] where P = (Fo2 + 2Fc2)/3 |
3581 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
F1 | 0.2727 (2) | 0.8570 (2) | 0.2869 (2) | 0.1094 (5) | |
N1 | 0.4381 (2) | 0.5326 (1) | 0.3309 (1) | 0.0631 (4) | |
C1 | 0.2847 (3) | 0.8556 (2) | 0.4123 (2) | 0.0709 (5) | |
C2 | 0.2450 (3) | 0.9653 (2) | 0.5167 (3) | 0.0871 (6) | |
C3 | 0.2550 (3) | 0.9619 (2) | 0.6419 (3) | 0.0922 (7) | |
C4 | 0.3042 (3) | 0.8524 (3) | 0.6628 (2) | 0.0893 (7) | |
C5 | 0.3449 (3) | 0.7437 (2) | 0.5571 (2) | 0.0730 (5) | |
C6 | 0.3362 (2) | 0.7436 (2) | 0.4289 (2) | 0.0587 (4) | |
C7 | 0.3769 (2) | 0.6283 (2) | 0.3139 (2) | 0.0589 (4) | |
C8 | 0.4728 (2) | 0.4228 (2) | 0.2145 (2) | 0.0579 (4) | |
C9 | 0.3656 (2) | 0.2868 (2) | 0.1577 (2) | 0.0653 (5) | |
C10 | 0.4009 (3) | 0.1789 (2) | 0.0461 (2) | 0.0762 (5) | |
C11 | 0.5372 (3) | 0.2037 (2) | −0.0054 (2) | 0.0794 (6) | |
C12 | 0.6437 (3) | 0.3368 (2) | 0.0545 (2) | 0.0728 (5) | |
C13 | 0.6153 (2) | 0.4494 (2) | 0.1660 (2) | 0.0638 (4) | |
C14 | 0.2158 (3) | 0.2608 (2) | 0.2161 (3) | 0.0826 (6) | |
C15 | 0.1957 (4) | 0.1246 (3) | 0.2351 (4) | 0.128 (1) | |
C16 | 0.0602 (4) | 0.2654 (4) | 0.1334 (4) | 0.143 (1) | |
C17 | 0.7400 (3) | 0.5944 (2) | 0.2390 (2) | 0.0802 (6) | |
C18 | 0.8511 (4) | 0.6052 (3) | 0.3690 (3) | 0.119 (1) | |
C19 | 0.8430 (4) | 0.6286 (3) | 0.1478 (3) | 0.1081 (8) | |
H2 | 0.2121 | 1.0401 | 0.5023 | 0.105* | |
H3 | 0.2281 | 1.0349 | 0.7138 | 0.111* | |
H4 | 0.3102 | 0.8510 | 0.7486 | 0.107* | |
H5 | 0.3787 | 0.6696 | 0.5724 | 0.088* | |
H7 | 0.3568 | 0.6263 | 0.2263 | 0.071* | |
H10 | 0.3305 | 0.0880 | 0.0056 | 0.091* | |
H11 | 0.5576 | 0.1303 | −0.0811 | 0.095* | |
H12 | 0.7371 | 0.3518 | 0.0196 | 0.087* | |
H14 | 0.2359 | 0.3401 | 0.3086 | 0.099* | |
H15a | 0.0995 | 0.1143 | 0.2729 | 0.192* | |
H15b | 0.2946 | 0.1292 | 0.2974 | 0.192* | |
H15c | 0.1802 | 0.0442 | 0.1469 | 0.192* | |
H16a | −0.0325 | 0.2479 | 0.1725 | 0.215* | |
H16b | 0.0401 | 0.1934 | 0.0397 | 0.215* | |
H16c | 0.0713 | 0.3578 | 0.1339 | 0.215* | |
H17 | 0.6741 | 0.6672 | 0.2685 | 0.096* | |
H18a | 0.7823 | 0.5823 | 0.4243 | 0.178* | |
H18b | 0.9186 | 0.7009 | 0.4213 | 0.178* | |
H18c | 0.9230 | 0.5395 | 0.3439 | 0.178* | |
H19a | 0.7752 | 0.6563 | 0.0871 | 0.162* | |
H19b | 0.8806 | 0.5457 | 0.0936 | 0.162* | |
H19c | 0.9387 | 0.7056 | 0.2048 | 0.162* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.173 (1) | 0.0938 (9) | 0.1050 (10) | 0.0689 (9) | 0.0614 (10) | 0.0635 (8) |
N1 | 0.076 (1) | 0.055 (1) | 0.058 (1) | 0.020 (1) | 0.015 (1) | 0.023 (1) |
C1 | 0.083 (1) | 0.060 (1) | 0.075 (1) | 0.022 (1) | 0.026 (1) | 0.030 (1) |
C2 | 0.100 (2) | 0.058 (1) | 0.102 (2) | 0.030 (1) | 0.033 (1) | 0.027 (1) |
C3 | 0.098 (2) | 0.076 (1) | 0.082 (1) | 0.027 (1) | 0.030 (1) | 0.008 (1) |
C4 | 0.104 (2) | 0.092 (2) | 0.061 (1) | 0.025 (1) | 0.023 (1) | 0.020 (1) |
C5 | 0.083 (1) | 0.070 (1) | 0.063 (1) | 0.021 (1) | 0.015 (1) | 0.025 (1) |
C6 | 0.058 (1) | 0.051 (1) | 0.062 (1) | 0.010 (1) | 0.014 (1) | 0.021 (1) |
C7 | 0.066 (1) | 0.053 (1) | 0.057 (1) | 0.016 (1) | 0.015 (1) | 0.023 (1) |
C8 | 0.070 (1) | 0.052 (1) | 0.054 (1) | 0.024 (1) | 0.011 (1) | 0.023 (1) |
C9 | 0.075 (1) | 0.055 (1) | 0.068 (1) | 0.020 (1) | 0.015 (1) | 0.028 (1) |
C10 | 0.090 (1) | 0.053 (1) | 0.076 (1) | 0.021 (1) | 0.015 (1) | 0.020 (1) |
C11 | 0.097 (2) | 0.068 (1) | 0.068 (1) | 0.036 (1) | 0.022 (1) | 0.018 (1) |
C12 | 0.073 (1) | 0.078 (1) | 0.071 (1) | 0.031 (1) | 0.021 (1) | 0.030 (1) |
C13 | 0.068 (1) | 0.060 (1) | 0.064 (1) | 0.022 (1) | 0.012 (1) | 0.027 (1) |
C14 | 0.090 (1) | 0.062 (1) | 0.097 (2) | 0.017 (1) | 0.033 (1) | 0.033 (1) |
C15 | 0.123 (2) | 0.125 (2) | 0.189 (3) | 0.035 (2) | 0.058 (2) | 0.111 (2) |
C16 | 0.092 (2) | 0.199 (4) | 0.216 (4) | 0.059 (2) | 0.057 (2) | 0.150 (3) |
C17 | 0.071 (1) | 0.071 (1) | 0.090 (1) | 0.016 (1) | 0.022 (1) | 0.025 (1) |
C18 | 0.106 (2) | 0.128 (2) | 0.085 (2) | −0.022 (2) | 0.000 (1) | 0.035 (2) |
C19 | 0.110 (2) | 0.099 (2) | 0.121 (2) | 0.007 (2) | 0.028 (2) | 0.059 (2) |
Geometric parameters (Å, º) top
F1—C1 | 1.354 (2) | C2—H2 | 0.93 |
N1—C7 | 1.253 (2) | C3—H3 | 0.93 |
N1—C8 | 1.427 (2) | C4—H4 | 0.93 |
C1—C2 | 1.373 (3) | C5—H5 | 0.93 |
C1—C6 | 1.377 (3) | C7—H7 | 0.93 |
C2—C3 | 1.363 (3) | C10—H10 | 0.93 |
C3—C4 | 1.364 (3) | C11—H11 | 0.93 |
C4—C5 | 1.379 (3) | C12—H12 | 0.93 |
C5—C6 | 1.381 (3) | C14—H14 | 0.98 |
C6—C7 | 1.469 (2) | C15—H15a | 0.96 |
C8—C9 | 1.400 (2) | C15—H15b | 0.96 |
C8—C13 | 1.398 (3) | C15—H15c | 0.96 |
C9—C10 | 1.388 (3) | C16—H16a | 0.96 |
C9—C14 | 1.513 (3) | C16—H16b | 0.96 |
C10—C11 | 1.368 (3) | C16—H16c | 0.96 |
C11—C12 | 1.373 (3) | C17—H17 | 0.98 |
C12—C13 | 1.388 (2) | C18—H18a | 0.96 |
C13—C17 | 1.526 (3) | C18—H18b | 0.96 |
C14—C16 | 1.470 (4) | C18—H18c | 0.96 |
C14—C15 | 1.516 (3) | C19—H19a | 0.96 |
C17—C18 | 1.512 (4) | C19—H19b | 0.96 |
C17—C19 | 1.513 (3) | C19—H19c | 0.96 |
C7—N1—C8 | 118.9 (1) | N1—C7—H7 | 119.1 |
F1—C1—C2 | 118.8 (2) | C6—C7—H7 | 119.1 |
F1—C1—C6 | 118.1 (2) | C11—C10—H10 | 119.3 |
C2—C1—C6 | 123.1 (2) | C9—C10—H10 | 119.3 |
C3—C2—C1 | 118.4 (2) | C10—C11—H11 | 120.0 |
C4—C3—C2 | 120.6 (2) | C12—C11—H11 | 120.0 |
C3—C4—C5 | 120.3 (2) | C11—C12—H12 | 119.2 |
C6—C5—C4 | 120.8 (2) | C13—C12—H12 | 119.2 |
C5—C6—C1 | 116.9 (2) | C16—C14—H14 | 106.8 |
C5—C6—C7 | 121.9 (2) | C9—C14—H14 | 106.8 |
C1—C6—C7 | 121.1 (2) | C15—C14—H14 | 106.8 |
N1—C7—C6 | 121.7 (2) | C14—C15—H15a | 109.5 |
C9—C8—C13 | 121.9 (2) | C14—C15—H15b | 109.5 |
C9—C8—N1 | 117.5 (2) | H15a—C15—H15b | 109.5 |
C13—C8—N1 | 120.5 (2) | C14—C15—H15c | 109.5 |
C10—C9—C8 | 117.7 (2) | H15a—C15—H15c | 109.5 |
C10—C9—C14 | 121.9 (2) | H15b—C15—H15c | 109.5 |
C8—C9—C14 | 120.4 (2) | C14—C16—H16a | 109.5 |
C11—C10—C9 | 121.4 (2) | C14—C16—H16b | 109.5 |
C10—C11—C12 | 120.0 (2) | H16a—C16—H16b | 109.5 |
C11—C12—C13 | 121.5 (2) | C14—C16—H16c | 109.5 |
C12—C13—C8 | 117.5 (2) | H16a—C16—H16c | 109.5 |
C12—C13—C17 | 121.5 (2) | H16b—C16—H16c | 109.5 |
C8—C13—C17 | 120.9 (2) | C18—C17—H17 | 107.0 |
C16—C14—C9 | 111.4 (2) | C19—C17—H17 | 107.0 |
C16—C14—C15 | 111.4 (2) | C13—C17—H17 | 107.0 |
C9—C14—C15 | 113.3 (2) | C17—C18—H18a | 109.5 |
C18—C17—C19 | 111.4 (2) | C17—C18—H18b | 109.5 |
C18—C17—C13 | 109.7 (2) | H18a—C18—H18b | 109.5 |
C19—C17—C13 | 114.2 (2) | C17—C18—H18c | 109.5 |
C3—C2—H2 | 120.8 | H18a—C18—H18c | 109.5 |
C1—C2—H2 | 120.8 | H18b—C18—H18c | 109.5 |
C4—C3—H3 | 119.7 | C17—C19—H19a | 109.5 |
C2—C3—H3 | 119.7 | C17—C19—H19b | 109.5 |
C3—C4—H4 | 119.9 | H19a—C19—H19b | 109.5 |
C5—C4—H4 | 119.9 | C17—C19—H19c | 109.5 |
C6—C5—H5 | 119.6 | H19a—C19—H19c | 109.5 |
C4—C5—H5 | 119.6 | H19b—C19—H19c | 109.5 |
F1—C1—C2—C3 | 179.0 (2) | N1—C8—C9—C14 | 2.0 (2) |
C6—C1—C2—C3 | −0.9 (3) | C8—C9—C10—C11 | 1.0 (3) |
C1—C2—C3—C4 | 0.3 (4) | C14—C9—C10—C11 | −179.7 (2) |
C2—C3—C4—C5 | 0.2 (4) | C9—C10—C11—C12 | 1.0 (3) |
C3—C4—C5—C6 | −0.2 (3) | C10—C11—C12—C13 | −1.2 (3) |
C4—C5—C6—C1 | −0.3 (3) | C11—C12—C13—C8 | −0.6 (3) |
C4—C5—C6—C7 | −179.2 (2) | C11—C12—C13—C17 | 175.7 (2) |
F1—C1—C6—C5 | −179.1 (2) | C9—C8—C13—C12 | 2.7 (3) |
C2—C1—C6—C5 | 0.8 (3) | N1—C8—C13—C12 | 178.4 (2) |
F1—C1—C6—C7 | −0.1 (3) | C9—C8—C13—C17 | −173.7 (2) |
C2—C1—C6—C7 | 179.8 (2) | N1—C8—C13—C17 | 2.1 (2) |
C8—N1—C7—C6 | 179.2 (1) | C10—C9—C14—C16 | −81.1 (3) |
C5—C6—C7—N1 | −7.5 (3) | C8—C9—C14—C16 | 98.1 (3) |
C1—C6—C7—N1 | 173.6 (2) | C10—C9—C14—C15 | 45.4 (3) |
C7—N1—C8—C9 | −106.6 (2) | C8—C9—C14—C15 | −135.4 (2) |
C7—N1—C8—C13 | 77.5 (2) | C12—C13—C17—C18 | −98.5 (2) |
C13—C8—C9—C10 | −2.9 (3) | C8—C13—C17—C18 | 77.7 (2) |
N1—C8—C9—C10 | −178.7 (2) | C12—C13—C17—C19 | 27.4 (3) |
C13—C8—C9—C14 | 177.9 (2) | C8—C13—C17—C19 | −156.4 (2) |
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