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The title compound, C
20H
18F
6N
2, a Schiff base, was synthesized by the reaction of 1,4-diaminobutane and 4-(trifluoromethyl)benzaldehyde in chloroform solution and was crystallized from a mixture of ethanol and dichloromethane (1:1). It lies across a crystallographic inversion centre. The crystal packing is stabilized by C—H
F hydrogen bonds and π–π interactions.
Supporting information
CCDC reference: 639047
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.048
- wR factor = 0.130
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.67 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1B .. F2 .. 2.64 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C5 .. N1 .. 96.60 Deg.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL and local programs.
N,
N'-Bis[4-(trifluoromethyl)benzylidene]butane-1,4-diamine
top
Crystal data top
C20H18F6N2 | F(000) = 412 |
Mr = 400.36 | Dx = 1.429 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0107 (16) Å | Cell parameters from 5528 reflections |
b = 9.8541 (14) Å | θ = 2.3–28.2° |
c = 8.6457 (13) Å | µ = 0.13 mm−1 |
β = 97.266 (2)° | T = 150 K |
V = 930.5 (2) Å3 | Needle, colourless |
Z = 2 | 0.40 × 0.40 × 0.20 mm |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2233 independent reflections |
Radiation source: fine-focus sealed tube | 1930 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
thin–slice ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −14→14 |
Tmin = 0.951, Tmax = 0.975 | k = −13→13 |
7930 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters not defined |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.5677P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.62 e Å−3 |
2233 reflections | Δρmin = −0.47 e Å−3 |
128 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.008 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: direct methods |
Secondary atom site location: difference Fourier map | |
Special details top
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. 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 | x | y | z | Uiso*/Ueq | |
F1 | 0.86376 (11) | 0.45527 (13) | 0.4359 (2) | 0.0874 (6) | |
F2 | 0.86324 (11) | 0.63264 (18) | 0.57845 (14) | 0.0699 (5) | |
F3 | 0.88920 (10) | 0.65049 (13) | 0.34219 (14) | 0.0534 (3) | |
N1 | 0.26168 (11) | 0.60794 (13) | 0.11012 (15) | 0.0302 (3) | |
C1 | 0.06754 (13) | 0.49162 (15) | 0.03096 (17) | 0.0289 (3) | |
H1A | 0.1096 | 0.4444 | −0.0482 | 0.035* | |
H1B | 0.0752 | 0.4344 | 0.1258 | 0.035* | |
C2 | 0.12979 (13) | 0.62782 (16) | 0.0699 (2) | 0.0325 (3) | |
H2A | 0.1143 | 0.6894 | −0.0209 | 0.039* | |
H2B | 0.0955 | 0.6701 | 0.1587 | 0.039* | |
C3 | 0.30888 (13) | 0.63977 (14) | 0.24629 (17) | 0.0275 (3) | |
H3 | 0.2582 | 0.6769 | 0.3167 | 0.033* | |
C4 | 0.44052 (13) | 0.62075 (14) | 0.29868 (16) | 0.0248 (3) | |
C5 | 0.51224 (14) | 0.53847 (15) | 0.21434 (16) | 0.0276 (3) | |
H5 | 0.4751 | 0.4909 | 0.1251 | 0.033* | |
C6 | 0.63664 (14) | 0.52585 (15) | 0.25993 (17) | 0.0293 (3) | |
H6 | 0.6852 | 0.4707 | 0.2017 | 0.035* | |
C7 | 0.69042 (14) | 0.59468 (15) | 0.39209 (17) | 0.0282 (3) | |
C8 | 0.62012 (15) | 0.67388 (16) | 0.47878 (18) | 0.0318 (3) | |
H8 | 0.6572 | 0.7194 | 0.5696 | 0.038* | |
C9 | 0.49523 (14) | 0.68647 (15) | 0.43237 (17) | 0.0296 (3) | |
H9 | 0.4468 | 0.7402 | 0.4921 | 0.035* | |
C10 | 0.82603 (15) | 0.58230 (17) | 0.4377 (2) | 0.0349 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0366 (6) | 0.0342 (6) | 0.1846 (18) | 0.0086 (5) | −0.0128 (8) | 0.0088 (8) |
F2 | 0.0410 (6) | 0.1268 (13) | 0.0384 (6) | 0.0074 (7) | −0.0085 (5) | −0.0083 (7) |
F3 | 0.0351 (6) | 0.0724 (8) | 0.0530 (7) | −0.0101 (5) | 0.0071 (5) | 0.0127 (6) |
N1 | 0.0252 (6) | 0.0314 (6) | 0.0344 (7) | −0.0054 (5) | 0.0054 (5) | −0.0025 (5) |
C1 | 0.0266 (7) | 0.0287 (7) | 0.0306 (7) | −0.0029 (6) | 0.0005 (6) | 0.0000 (6) |
C2 | 0.0259 (7) | 0.0311 (8) | 0.0402 (8) | −0.0035 (6) | 0.0032 (6) | −0.0014 (6) |
C3 | 0.0281 (7) | 0.0244 (7) | 0.0316 (7) | −0.0027 (5) | 0.0097 (6) | −0.0023 (5) |
C4 | 0.0290 (7) | 0.0220 (6) | 0.0243 (6) | −0.0022 (5) | 0.0068 (5) | 0.0012 (5) |
C5 | 0.0327 (7) | 0.0265 (7) | 0.0239 (7) | −0.0014 (6) | 0.0054 (5) | −0.0032 (5) |
C6 | 0.0324 (7) | 0.0279 (7) | 0.0288 (7) | 0.0031 (6) | 0.0089 (6) | −0.0005 (5) |
C7 | 0.0295 (7) | 0.0254 (7) | 0.0294 (7) | −0.0008 (5) | 0.0031 (6) | 0.0063 (5) |
C8 | 0.0369 (8) | 0.0308 (7) | 0.0265 (7) | −0.0017 (6) | 0.0001 (6) | −0.0041 (6) |
C9 | 0.0347 (8) | 0.0275 (7) | 0.0273 (7) | 0.0012 (6) | 0.0071 (6) | −0.0054 (5) |
C10 | 0.0330 (8) | 0.0325 (8) | 0.0384 (8) | −0.0002 (6) | 0.0021 (6) | 0.0053 (6) |
Geometric parameters (Å, º) top
F1—C10 | 1.320 (2) | C3—H3 | 0.9500 |
F2—C10 | 1.330 (2) | C4—C9 | 1.394 (2) |
F3—C10 | 1.3277 (19) | C4—C5 | 1.3995 (19) |
N1—C3 | 1.265 (2) | C5—C6 | 1.382 (2) |
N1—C2 | 1.4630 (19) | C5—H5 | 0.9500 |
C1—C1i | 1.525 (3) | C6—C7 | 1.395 (2) |
C1—C2 | 1.525 (2) | C6—H6 | 0.9500 |
C1—H1A | 0.9900 | C7—C8 | 1.384 (2) |
C1—H1B | 0.9900 | C7—C10 | 1.500 (2) |
C2—H2A | 0.9900 | C8—C9 | 1.388 (2) |
C2—H2B | 0.9900 | C8—H8 | 0.9500 |
C3—C4 | 1.475 (2) | C9—H9 | 0.9500 |
| | | |
C3—N1—C2 | 117.82 (13) | C6—C5—H5 | 119.7 |
C1i—C1—C2 | 111.92 (15) | C4—C5—H5 | 119.7 |
C1i—C1—H1A | 109.2 | C5—C6—C7 | 119.51 (13) |
C2—C1—H1A | 109.2 | C5—C6—H6 | 120.2 |
C1i—C1—H1B | 109.2 | C7—C6—H6 | 120.2 |
C2—C1—H1B | 109.2 | C8—C7—C6 | 120.61 (14) |
H1A—C1—H1B | 107.9 | C8—C7—C10 | 120.63 (14) |
N1—C2—C1 | 109.85 (12) | C6—C7—C10 | 118.76 (14) |
N1—C2—H2A | 109.7 | C7—C8—C9 | 119.67 (14) |
C1—C2—H2A | 109.7 | C7—C8—H8 | 120.2 |
N1—C2—H2B | 109.7 | C9—C8—H8 | 120.2 |
C1—C2—H2B | 109.7 | C8—C9—C4 | 120.44 (13) |
H2A—C2—H2B | 108.2 | C8—C9—H9 | 119.8 |
N1—C3—C4 | 121.78 (13) | C4—C9—H9 | 119.8 |
N1—C3—H3 | 119.1 | F1—C10—F3 | 106.39 (16) |
C4—C3—H3 | 119.1 | F1—C10—F2 | 107.68 (16) |
C9—C4—C5 | 119.22 (14) | F3—C10—F2 | 104.79 (14) |
C9—C4—C3 | 120.05 (13) | F1—C10—C7 | 112.23 (14) |
C5—C4—C3 | 120.73 (13) | F3—C10—C7 | 112.18 (13) |
C6—C5—C4 | 120.51 (13) | F2—C10—C7 | 113.05 (14) |
| | | |
C3—N1—C2—C1 | −117.61 (15) | C10—C7—C8—C9 | 178.49 (14) |
C1i—C1—C2—N1 | −173.00 (15) | C7—C8—C9—C4 | −0.5 (2) |
C2—N1—C3—C4 | 178.71 (13) | C5—C4—C9—C8 | 2.0 (2) |
N1—C3—C4—C9 | 163.95 (14) | C3—C4—C9—C8 | −177.19 (13) |
N1—C3—C4—C5 | −15.2 (2) | C8—C7—C10—F1 | 133.35 (17) |
C9—C4—C5—C6 | −2.1 (2) | C6—C7—C10—F1 | −47.2 (2) |
C3—C4—C5—C6 | 177.05 (13) | C8—C7—C10—F3 | −106.92 (17) |
C4—C5—C6—C7 | 0.7 (2) | C6—C7—C10—F3 | 72.53 (18) |
C5—C6—C7—C8 | 0.8 (2) | C8—C7—C10—F2 | 11.3 (2) |
C5—C6—C7—C10 | −178.63 (13) | C6—C7—C10—F2 | −169.23 (14) |
C6—C7—C8—C9 | −1.0 (2) | | |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N1 | 0.95 | 2.61 | 2.875 (2) | 97 |
C1—H1B···F2ii | 0.99 | 2.65 | 3.582 (2) | 158 |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
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