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At 150 K, the two imine groups of the title compound, C20H12F12N2, are mutually trans. The molecule has crystallographic inversion symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302508X/rn6003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302508X/rn6003Isup2.hkl
Contains datablock I

CCDC reference: 227866

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.059
  • wR factor = 0.192
  • Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C10
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C9 PLAT301_ALERT_3_C Main Residue Disorder ......................... 15.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 2 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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: X-STEP32 (Stoe & Cie, 2001) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX.

[3,5-Bis(trifluoromethyl)phenyl]{(E)-2-[(E)-3,5- bis(trifluoromethyl)phenylimino]-1-methylpropylidene}amine top
Crystal data top
C20H12F12N2Z = 1
Mr = 508.32F(000) = 254
Triclinic, P1Dx = 1.643 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1406 (12) ÅCell parameters from 8717 reflections
b = 8.2225 (12) Åθ = 2.5–32.3°
c = 8.7087 (13) ŵ = 0.17 mm1
α = 82.044 (12)°T = 150 K
β = 71.590 (11)°Lath, colourless
γ = 68.264 (11)°0.60 × 0.30 × 0.10 mm
V = 513.62 (13) Å3
Data collection top
Stoe IPDS-II
diffractometer
2477 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 32.3°, θmin = 2.5°
ω scansh = 1212
10945 measured reflectionsk = 1212
3638 independent reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.192 w = 1/[σ2(Fo2) + (0.1038P)2 + 0.0549P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
3638 reflectionsΔρmax = 0.62 e Å3
166 parametersΔρmin = 0.45 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.065 (17)
Special details top

Experimental. The crystal was mounted under the perfluoro-polyether PFO-XR75 (Lancaster Synthesis). A total of 290 frames (1 minute exposure) were collected (phi/omega: 10/175–180, 55/25–165, 160/25–170, delta-omega = 1 °.)

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807).

Plane 1

Atom d s d/s (d/s)**2 C1 * 0.0000 0.0016 0.000 0.000 N1 * 0.0000 0.0015 0.000 0.000 C2 * 0.0000 0.0020 0.000 0.000 C3 0.0527 0.0016 32.357 1047.007 ============ Sum((d/s)**2) for starred atoms 0.000

Plane 2

Atom d s d/s (d/s)**2 C3 * 0.0011 0.0014 0.796 0.634 C4 * 0.0036 0.0015 2.397 5.748 C5 * -0.0033 0.0015 - 2.174 4.725 C6 * -0.0021 0.0014 - 1.427 2.037 C7 * 0.0073 0.0015 4.852 23.542 C8 * -0.0067 0.0015 - 4.460 19.887 N1 - 0.1344 0.0013 - 105.129 11052.209 C9 - 0.0046 0.0020 - 2.304 5.308 C10 - 0.0108 0.0018 - 5.874 34.507 ============ Sum((d/s)**2) for starred atoms 56.573

Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 3

Atom d s d/s (d/s)**2 N1 * 0.0000 0.0013 0.000 0.000 C4 * 0.0000 0.0015 0.000 0.000 C8 * 0.0000 0.0015 0.000 0.000 C3 0.0471 0.0014 32.873 1080.603 ============ Sum((d/s)**2) for starred atoms 0.000

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 77.25 (0.12) 102.75 (0.12)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.8750 (2)0.7737 (2)0.0966 (2)0.0691 (4)
F20.8530 (2)0.7511 (3)0.3476 (2)0.0840 (6)
F31.00766 (17)0.5284 (2)0.1932 (2)0.0699 (5)
F40.4303 (3)0.2896 (2)0.0917 (3)0.0693 (6)0.887 (2)
F50.4953 (5)0.1598 (2)0.2999 (2)0.0918 (9)0.887 (2)
F60.7091 (3)0.1735 (3)0.0907 (4)0.0996 (10)0.887 (2)
F70.641 (3)0.1373 (17)0.228 (3)0.0693 (6)0.113 (2)
F80.614 (5)0.249 (2)0.0361 (17)0.0918 (9)0.113 (2)
F90.377 (2)0.244 (3)0.239 (3)0.0996 (10)0.113 (2)
N10.18628 (17)0.80521 (17)0.48625 (15)0.0303 (3)
C10.08685 (19)0.95044 (18)0.43766 (17)0.0267 (3)
C20.1239 (2)1.0281 (2)0.2698 (2)0.0391 (4)
H2C0.24260.95310.20210.047*
H2B0.12821.14500.27340.047*
H2A0.02531.03700.22390.047*
C30.35389 (19)0.69984 (18)0.38339 (17)0.0272 (3)
C40.5147 (2)0.73974 (18)0.34964 (18)0.0296 (3)
H40.50940.84550.38660.036*
C50.6824 (2)0.6240 (2)0.26176 (18)0.0299 (3)
C60.6941 (2)0.46924 (19)0.20517 (17)0.0298 (3)
H60.80920.39070.14530.036*
C70.5334 (2)0.43248 (19)0.23842 (18)0.0294 (3)
C80.3644 (2)0.54413 (19)0.32800 (18)0.0295 (3)
H80.25660.51460.35140.035*
C90.8534 (2)0.6686 (3)0.2271 (2)0.0417 (4)
C100.5418 (3)0.2648 (2)0.1809 (2)0.0386 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0545 (8)0.0723 (9)0.0774 (10)0.0373 (7)0.0046 (7)0.0178 (7)
F20.0597 (9)0.1383 (16)0.0763 (10)0.0627 (10)0.0009 (7)0.0421 (10)
F30.0281 (6)0.0583 (8)0.1160 (13)0.0096 (5)0.0165 (7)0.0042 (8)
F40.1058 (14)0.0449 (8)0.0876 (12)0.0263 (8)0.0693 (11)0.0009 (7)
F50.205 (3)0.0450 (9)0.0498 (9)0.0684 (14)0.0447 (13)0.0113 (7)
F60.0545 (11)0.0784 (13)0.155 (3)0.0102 (9)0.0036 (12)0.0842 (16)
F70.1058 (14)0.0449 (8)0.0876 (12)0.0263 (8)0.0693 (11)0.0009 (7)
F80.205 (3)0.0450 (9)0.0498 (9)0.0684 (14)0.0447 (13)0.0113 (7)
F90.0545 (11)0.0784 (13)0.155 (3)0.0102 (9)0.0036 (12)0.0842 (16)
N10.0252 (6)0.0275 (6)0.0303 (6)0.0022 (4)0.0053 (4)0.0024 (4)
C10.0229 (6)0.0248 (6)0.0299 (6)0.0055 (5)0.0066 (5)0.0032 (5)
C20.0319 (8)0.0354 (8)0.0321 (7)0.0013 (6)0.0022 (6)0.0021 (6)
C30.0252 (6)0.0241 (6)0.0266 (6)0.0031 (5)0.0067 (5)0.0001 (5)
C40.0293 (7)0.0246 (6)0.0319 (7)0.0064 (5)0.0079 (5)0.0017 (5)
C50.0253 (6)0.0306 (6)0.0304 (6)0.0078 (5)0.0066 (5)0.0016 (5)
C60.0249 (6)0.0282 (6)0.0286 (6)0.0025 (5)0.0046 (5)0.0026 (5)
C70.0302 (7)0.0257 (6)0.0292 (6)0.0050 (5)0.0092 (5)0.0024 (5)
C80.0264 (6)0.0278 (6)0.0322 (7)0.0065 (5)0.0085 (5)0.0019 (5)
C90.0290 (8)0.0429 (9)0.0498 (10)0.0129 (7)0.0048 (7)0.0043 (7)
C100.0427 (9)0.0310 (7)0.0409 (8)0.0074 (6)0.0142 (7)0.0078 (6)
Geometric parameters (Å, º) top
F1—C91.336 (2)C2—H2B0.9800
F2—C91.324 (3)C2—H2A0.9800
F3—C91.335 (2)C3—C81.394 (2)
F4—C101.316 (2)C3—C41.399 (2)
F5—C101.307 (3)C4—C51.391 (2)
F6—C101.329 (2)C4—H40.9500
F7—C101.176 (13)C5—C61.387 (2)
F8—C101.214 (16)C5—C91.498 (2)
F9—C101.345 (16)C6—C71.384 (2)
N1—C11.2731 (19)C6—H60.9500
N1—C31.4079 (18)C7—C81.389 (2)
C1—C21.497 (2)C7—C101.502 (2)
C1—C1i1.505 (3)C8—H80.9500
C2—H2C0.9800
C1—N1—C3121.92 (13)F2—C9—F3108.43 (18)
N1—C1—C2126.47 (13)F2—C9—F1105.95 (18)
N1—C1—C1i115.74 (16)F3—C9—F1104.06 (16)
C2—C1—C1i117.77 (15)F2—C9—C5112.63 (15)
C1—C2—H2C109.5F3—C9—C5112.76 (15)
C1—C2—H2B109.5F1—C9—C5112.42 (16)
H2C—C2—H2B109.5F7—C10—F899.7 (15)
C1—C2—H2A109.5F7—C10—F553.0 (12)
H2C—C2—H2A109.5F8—C10—F5134.4 (6)
H2B—C2—H2A109.5F7—C10—F4132.4 (6)
C8—C3—C4119.29 (13)F8—C10—F463.8 (15)
C8—C3—N1119.56 (13)F5—C10—F4105.4 (2)
C4—C3—N1120.81 (13)F7—C10—F656.5 (12)
C5—C4—C3119.74 (13)F8—C10—F646.2 (13)
C5—C4—H4120.1F5—C10—F6106.3 (2)
C3—C4—H4120.1F4—C10—F6105.8 (2)
C6—C5—C4121.40 (13)F7—C10—F9103.2 (15)
C6—C5—C9119.59 (14)F8—C10—F9116.5 (16)
C4—C5—C9119.01 (14)F5—C10—F953.4 (12)
C7—C6—C5118.12 (13)F4—C10—F957.0 (12)
C7—C6—H6120.9F6—C10—F9136.7 (5)
C5—C6—H6120.9F7—C10—C7114.4 (6)
C6—C7—C8121.81 (13)F8—C10—C7112.0 (6)
C6—C7—C10119.42 (13)F5—C10—C7112.76 (15)
C8—C7—C10118.74 (14)F4—C10—C7113.08 (15)
C7—C8—C3119.62 (14)F6—C10—C7112.89 (16)
C7—C8—H8120.2F9—C10—C7110.4 (5)
C3—C8—H8120.2
C3—N1—C1—C22.5 (2)C4—C5—C9—F235.6 (2)
C3—N1—C1—C1i179.06 (14)C6—C5—C9—F321.7 (2)
C1—N1—C3—C8107.89 (17)C4—C5—C9—F3158.67 (16)
C1—N1—C3—C478.82 (19)C6—C5—C9—F195.61 (19)
C8—C3—C4—C50.1 (2)C4—C5—C9—F184.1 (2)
N1—C3—C4—C5173.24 (13)C6—C7—C10—F757.6 (14)
C3—C4—C5—C60.5 (2)C8—C7—C10—F7120.6 (14)
C3—C4—C5—C9179.83 (14)C6—C7—C10—F854.9 (16)
C4—C5—C6—C70.0 (2)C8—C7—C10—F8127.0 (16)
C9—C5—C6—C7179.61 (15)C6—C7—C10—F5115.8 (2)
C5—C6—C7—C81.1 (2)C8—C7—C10—F562.4 (3)
C5—C6—C7—C10179.14 (14)C6—C7—C10—F4124.7 (2)
C6—C7—C8—C31.5 (2)C8—C7—C10—F457.2 (2)
C10—C7—C8—C3179.60 (14)C6—C7—C10—F64.7 (3)
C4—C3—C8—C70.9 (2)C8—C7—C10—F6177.2 (2)
N1—C3—C8—C7174.31 (13)C6—C7—C10—F9173.5 (14)
C6—C5—C9—F2144.78 (18)C8—C7—C10—F94.6 (14)
Symmetry code: (i) x, y+2, z+1.
 

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