[3,5-Bis­(tri­fluoro­methyl)­phenyl]{(E)-2-[(E)-3,5-bis­(tri­fluoro­methyl)­phenyl­imino]-1-methyl­propyl­idene}amine

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

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

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Computing details

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

Crystal data

C20H12F12N2	Z = 1
Mr = 508.32	F(000) = 254
Triclinic, P1	Dx = 1.643 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1406 (12) Å	Cell parameters from 8717 reflections
b = 8.2225 (12) Å	θ = 2.5–32.3°
c = 8.7087 (13) Å	µ = 0.17 mm^−1
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) Å^3

Data collection

Stoe IPDS-II diffractometer	2477 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 32.3°, θmin = 2.5°
ω scans	h = −12→12
10945 measured reflections	k = −12→12
3638 independent reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.192	w = 1/[σ^2(Fo^2) + (0.1038P)^2 + 0.0549P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
3638 reflections	Δρmax = 0.62 e Å^−3
166 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.065 (17)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.8750 (2)	0.7737 (2)	0.0966 (2)	0.0691 (4)
F2	0.8530 (2)	0.7511 (3)	0.3476 (2)	0.0840 (6)
F3	1.00766 (17)	0.5284 (2)	0.1932 (2)	0.0699 (5)
F4	0.4303 (3)	0.2896 (2)	0.0917 (3)	0.0693 (6)	0.887 (2)
F5	0.4953 (5)	0.1598 (2)	0.2999 (2)	0.0918 (9)	0.887 (2)
F6	0.7091 (3)	0.1735 (3)	0.0907 (4)	0.0996 (10)	0.887 (2)
F7	0.641 (3)	0.1373 (17)	0.228 (3)	0.0693 (6)	0.113 (2)
F8	0.614 (5)	0.249 (2)	0.0361 (17)	0.0918 (9)	0.113 (2)
F9	0.377 (2)	0.244 (3)	0.239 (3)	0.0996 (10)	0.113 (2)
N1	0.18628 (17)	0.80521 (17)	0.48625 (15)	0.0303 (3)
C1	0.08685 (19)	0.95044 (18)	0.43766 (17)	0.0267 (3)
C2	0.1239 (2)	1.0281 (2)	0.2698 (2)	0.0391 (4)
H2C	0.2426	0.9531	0.2021	0.047*
H2B	0.1282	1.1450	0.2734	0.047*
H2A	0.0253	1.0370	0.2239	0.047*
C3	0.35389 (19)	0.69984 (18)	0.38339 (17)	0.0272 (3)
C4	0.5147 (2)	0.73974 (18)	0.34964 (18)	0.0296 (3)
H4	0.5094	0.8455	0.3866	0.036*
C5	0.6824 (2)	0.6240 (2)	0.26176 (18)	0.0299 (3)
C6	0.6941 (2)	0.46924 (19)	0.20517 (17)	0.0298 (3)
H6	0.8092	0.3907	0.1453	0.036*
C7	0.5334 (2)	0.43248 (19)	0.23842 (18)	0.0294 (3)
C8	0.3644 (2)	0.54413 (19)	0.32800 (18)	0.0295 (3)
H8	0.2566	0.5146	0.3514	0.035*
C9	0.8534 (2)	0.6686 (3)	0.2271 (2)	0.0417 (4)
C10	0.5418 (3)	0.2648 (2)	0.1809 (2)	0.0386 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0545 (8)	0.0723 (9)	0.0774 (10)	−0.0373 (7)	−0.0046 (7)	0.0178 (7)
F2	0.0597 (9)	0.1383 (16)	0.0763 (10)	−0.0627 (10)	0.0009 (7)	−0.0421 (10)
F3	0.0281 (6)	0.0583 (8)	0.1160 (13)	−0.0096 (5)	−0.0165 (7)	−0.0042 (8)
F4	0.1058 (14)	0.0449 (8)	0.0876 (12)	−0.0263 (8)	−0.0693 (11)	0.0009 (7)
F5	0.205 (3)	0.0450 (9)	0.0498 (9)	−0.0684 (14)	−0.0447 (13)	0.0113 (7)
F6	0.0545 (11)	0.0784 (13)	0.155 (3)	−0.0102 (9)	0.0036 (12)	−0.0842 (16)
F7	0.1058 (14)	0.0449 (8)	0.0876 (12)	−0.0263 (8)	−0.0693 (11)	0.0009 (7)
F8	0.205 (3)	0.0450 (9)	0.0498 (9)	−0.0684 (14)	−0.0447 (13)	0.0113 (7)
F9	0.0545 (11)	0.0784 (13)	0.155 (3)	−0.0102 (9)	0.0036 (12)	−0.0842 (16)
N1	0.0252 (6)	0.0275 (6)	0.0303 (6)	−0.0022 (4)	−0.0053 (4)	−0.0024 (4)
C1	0.0229 (6)	0.0248 (6)	0.0299 (6)	−0.0055 (5)	−0.0066 (5)	−0.0032 (5)
C2	0.0319 (8)	0.0354 (8)	0.0321 (7)	0.0013 (6)	−0.0022 (6)	0.0021 (6)
C3	0.0252 (6)	0.0241 (6)	0.0266 (6)	−0.0031 (5)	−0.0067 (5)	−0.0001 (5)
C4	0.0293 (7)	0.0246 (6)	0.0319 (7)	−0.0064 (5)	−0.0079 (5)	−0.0017 (5)
C5	0.0253 (6)	0.0306 (6)	0.0304 (6)	−0.0078 (5)	−0.0066 (5)	0.0016 (5)
C6	0.0249 (6)	0.0282 (6)	0.0286 (6)	−0.0025 (5)	−0.0046 (5)	−0.0026 (5)
C7	0.0302 (7)	0.0257 (6)	0.0292 (6)	−0.0050 (5)	−0.0092 (5)	−0.0024 (5)
C8	0.0264 (6)	0.0278 (6)	0.0322 (7)	−0.0065 (5)	−0.0085 (5)	−0.0019 (5)
C9	0.0290 (8)	0.0429 (9)	0.0498 (10)	−0.0129 (7)	−0.0048 (7)	−0.0043 (7)
C10	0.0427 (9)	0.0310 (7)	0.0409 (8)	−0.0074 (6)	−0.0142 (7)	−0.0078 (6)

Geometric parameters (Å, º)

F1—C9	1.336 (2)	C2—H2B	0.9800
F2—C9	1.324 (3)	C2—H2A	0.9800
F3—C9	1.335 (2)	C3—C8	1.394 (2)
F4—C10	1.316 (2)	C3—C4	1.399 (2)
F5—C10	1.307 (3)	C4—C5	1.391 (2)
F6—C10	1.329 (2)	C4—H4	0.9500
F7—C10	1.176 (13)	C5—C6	1.387 (2)
F8—C10	1.214 (16)	C5—C9	1.498 (2)
F9—C10	1.345 (16)	C6—C7	1.384 (2)
N1—C1	1.2731 (19)	C6—H6	0.9500
N1—C3	1.4079 (18)	C7—C8	1.389 (2)
C1—C2	1.497 (2)	C7—C10	1.502 (2)
C1—C1^i	1.505 (3)	C8—H8	0.9500
C2—H2C	0.9800
C1—N1—C3	121.92 (13)	F2—C9—F3	108.43 (18)
N1—C1—C2	126.47 (13)	F2—C9—F1	105.95 (18)
N1—C1—C1^i	115.74 (16)	F3—C9—F1	104.06 (16)
C2—C1—C1^i	117.77 (15)	F2—C9—C5	112.63 (15)
C1—C2—H2C	109.5	F3—C9—C5	112.76 (15)
C1—C2—H2B	109.5	F1—C9—C5	112.42 (16)
H2C—C2—H2B	109.5	F7—C10—F8	99.7 (15)
C1—C2—H2A	109.5	F7—C10—F5	53.0 (12)
H2C—C2—H2A	109.5	F8—C10—F5	134.4 (6)
H2B—C2—H2A	109.5	F7—C10—F4	132.4 (6)
C8—C3—C4	119.29 (13)	F8—C10—F4	63.8 (15)
C8—C3—N1	119.56 (13)	F5—C10—F4	105.4 (2)
C4—C3—N1	120.81 (13)	F7—C10—F6	56.5 (12)
C5—C4—C3	119.74 (13)	F8—C10—F6	46.2 (13)
C5—C4—H4	120.1	F5—C10—F6	106.3 (2)
C3—C4—H4	120.1	F4—C10—F6	105.8 (2)
C6—C5—C4	121.40 (13)	F7—C10—F9	103.2 (15)
C6—C5—C9	119.59 (14)	F8—C10—F9	116.5 (16)
C4—C5—C9	119.01 (14)	F5—C10—F9	53.4 (12)
C7—C6—C5	118.12 (13)	F4—C10—F9	57.0 (12)
C7—C6—H6	120.9	F6—C10—F9	136.7 (5)
C5—C6—H6	120.9	F7—C10—C7	114.4 (6)
C6—C7—C8	121.81 (13)	F8—C10—C7	112.0 (6)
C6—C7—C10	119.42 (13)	F5—C10—C7	112.76 (15)
C8—C7—C10	118.74 (14)	F4—C10—C7	113.08 (15)
C7—C8—C3	119.62 (14)	F6—C10—C7	112.89 (16)
C7—C8—H8	120.2	F9—C10—C7	110.4 (5)
C3—C8—H8	120.2
C3—N1—C1—C2	2.5 (2)	C4—C5—C9—F2	35.6 (2)
C3—N1—C1—C1^i	−179.06 (14)	C6—C5—C9—F3	−21.7 (2)
C1—N1—C3—C8	−107.89 (17)	C4—C5—C9—F3	158.67 (16)
C1—N1—C3—C4	78.82 (19)	C6—C5—C9—F1	95.61 (19)
C8—C3—C4—C5	−0.1 (2)	C4—C5—C9—F1	−84.1 (2)
N1—C3—C4—C5	173.24 (13)	C6—C7—C10—F7	57.6 (14)
C3—C4—C5—C6	0.5 (2)	C8—C7—C10—F7	−120.6 (14)
C3—C4—C5—C9	−179.83 (14)	C6—C7—C10—F8	−54.9 (16)
C4—C5—C6—C7	0.0 (2)	C8—C7—C10—F8	127.0 (16)
C9—C5—C6—C7	−179.61 (15)	C6—C7—C10—F5	115.8 (2)
C5—C6—C7—C8	−1.1 (2)	C8—C7—C10—F5	−62.4 (3)
C5—C6—C7—C10	−179.14 (14)	C6—C7—C10—F4	−124.7 (2)
C6—C7—C8—C3	1.5 (2)	C8—C7—C10—F4	57.2 (2)
C10—C7—C8—C3	179.60 (14)	C6—C7—C10—F6	−4.7 (3)
C4—C3—C8—C7	−0.9 (2)	C8—C7—C10—F6	177.2 (2)
N1—C3—C8—C7	−174.31 (13)	C6—C7—C10—F9	173.5 (14)
C6—C5—C9—F2	−144.78 (18)	C8—C7—C10—F9	−4.6 (14)

Symmetry code: (i) −x, −y+2, −z+1.