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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008263/bt6629sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008263/bt6629Isup2.hkl
Contains datablock I

CCDC reference: 270246

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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
C19H22FNZ = 2
Mr = 283.38F(000) = 304
Triclinic, P1Dx = 1.136 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.265 (1) ÅCell parameters from 982 reflections
b = 10.510 (1) Åθ = 2.1–27.1°
c = 10.841 (1) ŵ = 0.07 mm1
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 tubeRint = 0.013
Graphite monochromatorθmax = 27.2°, θmin = 2.1°
φ and ω scansh = 1010
7091 measured reflectionsk = 1313
3581 independent reflectionsl = 1313
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.2727 (2)0.8570 (2)0.2869 (2)0.1094 (5)
N10.4381 (2)0.5326 (1)0.3309 (1)0.0631 (4)
C10.2847 (3)0.8556 (2)0.4123 (2)0.0709 (5)
C20.2450 (3)0.9653 (2)0.5167 (3)0.0871 (6)
C30.2550 (3)0.9619 (2)0.6419 (3)0.0922 (7)
C40.3042 (3)0.8524 (3)0.6628 (2)0.0893 (7)
C50.3449 (3)0.7437 (2)0.5571 (2)0.0730 (5)
C60.3362 (2)0.7436 (2)0.4289 (2)0.0587 (4)
C70.3769 (2)0.6283 (2)0.3139 (2)0.0589 (4)
C80.4728 (2)0.4228 (2)0.2145 (2)0.0579 (4)
C90.3656 (2)0.2868 (2)0.1577 (2)0.0653 (5)
C100.4009 (3)0.1789 (2)0.0461 (2)0.0762 (5)
C110.5372 (3)0.2037 (2)0.0054 (2)0.0794 (6)
C120.6437 (3)0.3368 (2)0.0545 (2)0.0728 (5)
C130.6153 (2)0.4494 (2)0.1660 (2)0.0638 (4)
C140.2158 (3)0.2608 (2)0.2161 (3)0.0826 (6)
C150.1957 (4)0.1246 (3)0.2351 (4)0.128 (1)
C160.0602 (4)0.2654 (4)0.1334 (4)0.143 (1)
C170.7400 (3)0.5944 (2)0.2390 (2)0.0802 (6)
C180.8511 (4)0.6052 (3)0.3690 (3)0.119 (1)
C190.8430 (4)0.6286 (3)0.1478 (3)0.1081 (8)
H20.21211.04010.50230.105*
H30.22811.03490.71380.111*
H40.31020.85100.74860.107*
H50.37870.66960.57240.088*
H70.35680.62630.22630.071*
H100.33050.08800.00560.091*
H110.55760.13030.08110.095*
H120.73710.35180.01960.087*
H140.23590.34010.30860.099*
H15a0.09950.11430.27290.192*
H15b0.29460.12920.29740.192*
H15c0.18020.04420.14690.192*
H16a0.03250.24790.17250.215*
H16b0.04010.19340.03970.215*
H16c0.07130.35780.13390.215*
H170.67410.66720.26850.096*
H18a0.78230.58230.42430.178*
H18b0.91860.70090.42130.178*
H18c0.92300.53950.34390.178*
H19a0.77520.65630.08710.162*
H19b0.88060.54570.09360.162*
H19c0.93870.70560.20480.162*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.173 (1)0.0938 (9)0.1050 (10)0.0689 (9)0.0614 (10)0.0635 (8)
N10.076 (1)0.055 (1)0.058 (1)0.020 (1)0.015 (1)0.023 (1)
C10.083 (1)0.060 (1)0.075 (1)0.022 (1)0.026 (1)0.030 (1)
C20.100 (2)0.058 (1)0.102 (2)0.030 (1)0.033 (1)0.027 (1)
C30.098 (2)0.076 (1)0.082 (1)0.027 (1)0.030 (1)0.008 (1)
C40.104 (2)0.092 (2)0.061 (1)0.025 (1)0.023 (1)0.020 (1)
C50.083 (1)0.070 (1)0.063 (1)0.021 (1)0.015 (1)0.025 (1)
C60.058 (1)0.051 (1)0.062 (1)0.010 (1)0.014 (1)0.021 (1)
C70.066 (1)0.053 (1)0.057 (1)0.016 (1)0.015 (1)0.023 (1)
C80.070 (1)0.052 (1)0.054 (1)0.024 (1)0.011 (1)0.023 (1)
C90.075 (1)0.055 (1)0.068 (1)0.020 (1)0.015 (1)0.028 (1)
C100.090 (1)0.053 (1)0.076 (1)0.021 (1)0.015 (1)0.020 (1)
C110.097 (2)0.068 (1)0.068 (1)0.036 (1)0.022 (1)0.018 (1)
C120.073 (1)0.078 (1)0.071 (1)0.031 (1)0.021 (1)0.030 (1)
C130.068 (1)0.060 (1)0.064 (1)0.022 (1)0.012 (1)0.027 (1)
C140.090 (1)0.062 (1)0.097 (2)0.017 (1)0.033 (1)0.033 (1)
C150.123 (2)0.125 (2)0.189 (3)0.035 (2)0.058 (2)0.111 (2)
C160.092 (2)0.199 (4)0.216 (4)0.059 (2)0.057 (2)0.150 (3)
C170.071 (1)0.071 (1)0.090 (1)0.016 (1)0.022 (1)0.025 (1)
C180.106 (2)0.128 (2)0.085 (2)0.022 (2)0.000 (1)0.035 (2)
C190.110 (2)0.099 (2)0.121 (2)0.007 (2)0.028 (2)0.059 (2)
Geometric parameters (Å, º) top
F1—C11.354 (2)C2—H20.93
N1—C71.253 (2)C3—H30.93
N1—C81.427 (2)C4—H40.93
C1—C21.373 (3)C5—H50.93
C1—C61.377 (3)C7—H70.93
C2—C31.363 (3)C10—H100.93
C3—C41.364 (3)C11—H110.93
C4—C51.379 (3)C12—H120.93
C5—C61.381 (3)C14—H140.98
C6—C71.469 (2)C15—H15a0.96
C8—C91.400 (2)C15—H15b0.96
C8—C131.398 (3)C15—H15c0.96
C9—C101.388 (3)C16—H16a0.96
C9—C141.513 (3)C16—H16b0.96
C10—C111.368 (3)C16—H16c0.96
C11—C121.373 (3)C17—H170.98
C12—C131.388 (2)C18—H18a0.96
C13—C171.526 (3)C18—H18b0.96
C14—C161.470 (4)C18—H18c0.96
C14—C151.516 (3)C19—H19a0.96
C17—C181.512 (4)C19—H19b0.96
C17—C191.513 (3)C19—H19c0.96
C7—N1—C8118.9 (1)N1—C7—H7119.1
F1—C1—C2118.8 (2)C6—C7—H7119.1
F1—C1—C6118.1 (2)C11—C10—H10119.3
C2—C1—C6123.1 (2)C9—C10—H10119.3
C3—C2—C1118.4 (2)C10—C11—H11120.0
C4—C3—C2120.6 (2)C12—C11—H11120.0
C3—C4—C5120.3 (2)C11—C12—H12119.2
C6—C5—C4120.8 (2)C13—C12—H12119.2
C5—C6—C1116.9 (2)C16—C14—H14106.8
C5—C6—C7121.9 (2)C9—C14—H14106.8
C1—C6—C7121.1 (2)C15—C14—H14106.8
N1—C7—C6121.7 (2)C14—C15—H15a109.5
C9—C8—C13121.9 (2)C14—C15—H15b109.5
C9—C8—N1117.5 (2)H15a—C15—H15b109.5
C13—C8—N1120.5 (2)C14—C15—H15c109.5
C10—C9—C8117.7 (2)H15a—C15—H15c109.5
C10—C9—C14121.9 (2)H15b—C15—H15c109.5
C8—C9—C14120.4 (2)C14—C16—H16a109.5
C11—C10—C9121.4 (2)C14—C16—H16b109.5
C10—C11—C12120.0 (2)H16a—C16—H16b109.5
C11—C12—C13121.5 (2)C14—C16—H16c109.5
C12—C13—C8117.5 (2)H16a—C16—H16c109.5
C12—C13—C17121.5 (2)H16b—C16—H16c109.5
C8—C13—C17120.9 (2)C18—C17—H17107.0
C16—C14—C9111.4 (2)C19—C17—H17107.0
C16—C14—C15111.4 (2)C13—C17—H17107.0
C9—C14—C15113.3 (2)C17—C18—H18a109.5
C18—C17—C19111.4 (2)C17—C18—H18b109.5
C18—C17—C13109.7 (2)H18a—C18—H18b109.5
C19—C17—C13114.2 (2)C17—C18—H18c109.5
C3—C2—H2120.8H18a—C18—H18c109.5
C1—C2—H2120.8H18b—C18—H18c109.5
C4—C3—H3119.7C17—C19—H19a109.5
C2—C3—H3119.7C17—C19—H19b109.5
C3—C4—H4119.9H19a—C19—H19b109.5
C5—C4—H4119.9C17—C19—H19c109.5
C6—C5—H5119.6H19a—C19—H19c109.5
C4—C5—H5119.6H19b—C19—H19c109.5
F1—C1—C2—C3179.0 (2)N1—C8—C9—C142.0 (2)
C6—C1—C2—C30.9 (3)C8—C9—C10—C111.0 (3)
C1—C2—C3—C40.3 (4)C14—C9—C10—C11179.7 (2)
C2—C3—C4—C50.2 (4)C9—C10—C11—C121.0 (3)
C3—C4—C5—C60.2 (3)C10—C11—C12—C131.2 (3)
C4—C5—C6—C10.3 (3)C11—C12—C13—C80.6 (3)
C4—C5—C6—C7179.2 (2)C11—C12—C13—C17175.7 (2)
F1—C1—C6—C5179.1 (2)C9—C8—C13—C122.7 (3)
C2—C1—C6—C50.8 (3)N1—C8—C13—C12178.4 (2)
F1—C1—C6—C70.1 (3)C9—C8—C13—C17173.7 (2)
C2—C1—C6—C7179.8 (2)N1—C8—C13—C172.1 (2)
C8—N1—C7—C6179.2 (1)C10—C9—C14—C1681.1 (3)
C5—C6—C7—N17.5 (3)C8—C9—C14—C1698.1 (3)
C1—C6—C7—N1173.6 (2)C10—C9—C14—C1545.4 (3)
C7—N1—C8—C9106.6 (2)C8—C9—C14—C15135.4 (2)
C7—N1—C8—C1377.5 (2)C12—C13—C17—C1898.5 (2)
C13—C8—C9—C102.9 (3)C8—C13—C17—C1877.7 (2)
N1—C8—C9—C10178.7 (2)C12—C13—C17—C1927.4 (3)
C13—C8—C9—C14177.9 (2)C8—C13—C17—C19156.4 (2)
 

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