The heterocyclic ring of the title compound, C18H21F2N3, adopts a chair conformation with two 4-fluorophenyl groups in axial and one propyl group in an equatorial position. The torsion angles around the N—C bonds in the triazacyclohexane are in the range 55.8 (3)–60.2 (3)°.
Supporting information
CCDC reference: 624714
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C)= 0.004 Å
- R factor = 0.070
- wR factor = 0.172
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3,5-Bis(4-fluorophenyl)-1-propyl-1,3,5-triazacyclohexane
top
Crystal data top
C18H21F2N3 | Z = 2 |
Mr = 317.38 | F(000) = 336 |
Triclinic, P1 | Dx = 1.299 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0610 (2) Å | Cell parameters from 13114 reflections |
b = 10.0150 (3) Å | θ = 3.0–25.8° |
c = 13.5200 (4) Å | µ = 0.09 mm−1 |
α = 91.444 (1)° | T = 150 K |
β = 92.406 (1)° | Prism, colourless |
γ = 98.1090 (17)° | 0.40 × 0.25 × 0.10 mm |
V = 811.35 (4) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 2711 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.049 |
Graphite monochromator | θmax = 25.8°, θmin = 3.0° |
φ scans, and ω scans with κ offsets | h = −7→7 |
13114 measured reflections | k = −12→12 |
3081 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.172 | w = 1/[σ2(Fo2) + (0.0293P)2 + 1.3984P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
3081 reflections | Δρmax = 0.30 e Å−3 |
208 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: none |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | 0.1490 (3) | 1.37408 (18) | 0.49254 (14) | 0.0460 (6) | |
F2 | 0.1334 (3) | 1.3903 (2) | 0.02191 (16) | 0.0523 (7) | |
N1 | 0.6623 (4) | 1.0075 (2) | 0.33762 (16) | 0.0266 (7) | |
N2 | 0.6623 (4) | 1.0175 (2) | 0.15764 (16) | 0.0267 (7) | |
N3 | 0.4298 (4) | 0.8369 (2) | 0.23585 (16) | 0.0267 (7) | |
C1 | 0.5700 (4) | 0.8658 (3) | 0.3273 (2) | 0.0286 (8) | |
C2 | 0.7929 (4) | 1.0466 (3) | 0.25076 (19) | 0.0282 (8) | |
C3 | 0.5713 (5) | 0.8754 (3) | 0.15234 (19) | 0.0287 (8) | |
C11 | 0.5238 (4) | 1.0994 (3) | 0.37361 (18) | 0.0242 (8) | |
C12 | 0.3049 (4) | 1.0595 (3) | 0.39970 (19) | 0.0271 (8) | |
C13 | 0.1796 (4) | 1.1508 (3) | 0.4408 (2) | 0.0294 (8) | |
C14 | 0.2725 (5) | 1.2831 (3) | 0.4522 (2) | 0.0320 (8) | |
C15 | 0.4874 (5) | 1.3284 (3) | 0.4272 (2) | 0.0351 (9) | |
C16 | 0.6125 (5) | 1.2354 (3) | 0.3890 (2) | 0.0319 (8) | |
C21 | 0.5196 (4) | 1.1118 (3) | 0.12794 (18) | 0.0248 (8) | |
C22 | 0.6097 (5) | 1.2472 (3) | 0.1203 (2) | 0.0301 (8) | |
C23 | 0.4797 (5) | 1.3413 (3) | 0.0866 (2) | 0.0351 (9) | |
C24 | 0.2606 (5) | 1.2988 (3) | 0.0584 (2) | 0.0360 (9) | |
C25 | 0.1652 (5) | 1.1667 (3) | 0.0649 (2) | 0.0321 (9) | |
C26 | 0.2949 (4) | 1.0732 (3) | 0.10124 (19) | 0.0279 (8) | |
C31 | 0.3343 (5) | 0.6941 (3) | 0.2251 (2) | 0.0332 (9) | |
C32 | 0.1518 (6) | 0.6525 (3) | 0.2955 (3) | 0.0436 (10) | |
C33 | 0.0198 (7) | 0.5153 (3) | 0.2667 (3) | 0.0551 (11) | |
H1A | 0.69328 | 0.81070 | 0.32677 | 0.0342* | |
H1B | 0.47966 | 0.84017 | 0.38497 | 0.0342* | |
H2A | 0.92363 | 0.99753 | 0.25032 | 0.0338* | |
H2B | 0.84879 | 1.14439 | 0.25633 | 0.0338* | |
H3A | 0.48206 | 0.85508 | 0.08939 | 0.0345* | |
H3B | 0.69549 | 0.82090 | 0.15237 | 0.0345* | |
H12 | 0.24002 | 0.96793 | 0.38913 | 0.0324* | |
H13 | 0.03236 | 1.12187 | 0.46059 | 0.0353* | |
H15 | 0.54819 | 1.42087 | 0.43589 | 0.0422* | |
H16 | 0.76227 | 1.26463 | 0.37280 | 0.0382* | |
H22 | 0.76259 | 1.27525 | 0.13848 | 0.0361* | |
H23 | 0.54124 | 1.43356 | 0.08303 | 0.0421* | |
H25 | 0.01301 | 1.13961 | 0.04479 | 0.0385* | |
H26 | 0.22946 | 0.98216 | 0.10794 | 0.0335* | |
H31A | 0.27324 | 0.67543 | 0.15627 | 0.0399* | |
H31B | 0.45488 | 0.63826 | 0.23625 | 0.0399* | |
H32A | 0.21900 | 0.64930 | 0.36325 | 0.0523* | |
H32B | 0.04912 | 0.72105 | 0.29618 | 0.0523* | |
H33A | −0.09603 | 0.49225 | 0.31434 | 0.0827* | |
H33B | −0.05010 | 0.51861 | 0.20028 | 0.0827* | |
H33C | 0.12035 | 0.44683 | 0.26697 | 0.0827* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0434 (10) | 0.0417 (10) | 0.0537 (12) | 0.0083 (8) | 0.0113 (9) | −0.0116 (8) |
F2 | 0.0467 (11) | 0.0510 (12) | 0.0640 (13) | 0.0211 (9) | 0.0027 (10) | 0.0153 (10) |
N1 | 0.0258 (11) | 0.0325 (12) | 0.0213 (11) | 0.0028 (9) | 0.0025 (9) | 0.0016 (9) |
N2 | 0.0259 (11) | 0.0330 (12) | 0.0209 (11) | 0.0023 (9) | 0.0023 (9) | 0.0012 (9) |
N3 | 0.0303 (12) | 0.0256 (12) | 0.0230 (11) | −0.0008 (9) | 0.0031 (9) | 0.0022 (9) |
C1 | 0.0286 (14) | 0.0305 (14) | 0.0267 (14) | 0.0034 (11) | 0.0038 (11) | 0.0034 (11) |
C2 | 0.0241 (13) | 0.0371 (15) | 0.0227 (13) | 0.0021 (11) | 0.0013 (10) | 0.0010 (11) |
C3 | 0.0307 (14) | 0.0330 (14) | 0.0224 (13) | 0.0027 (11) | 0.0055 (11) | 0.0016 (11) |
C11 | 0.0230 (13) | 0.0311 (14) | 0.0171 (12) | −0.0003 (10) | −0.0010 (10) | 0.0024 (10) |
C12 | 0.0246 (13) | 0.0314 (14) | 0.0230 (13) | −0.0030 (11) | −0.0017 (10) | 0.0031 (11) |
C13 | 0.0242 (13) | 0.0378 (15) | 0.0244 (13) | −0.0020 (11) | 0.0012 (10) | 0.0013 (11) |
C14 | 0.0322 (15) | 0.0354 (15) | 0.0281 (14) | 0.0045 (12) | 0.0005 (11) | −0.0036 (12) |
C15 | 0.0356 (16) | 0.0314 (15) | 0.0358 (16) | −0.0039 (12) | 0.0031 (12) | −0.0037 (12) |
C16 | 0.0256 (14) | 0.0355 (15) | 0.0322 (15) | −0.0041 (11) | 0.0043 (11) | −0.0001 (12) |
C21 | 0.0264 (13) | 0.0304 (14) | 0.0165 (12) | −0.0013 (11) | 0.0063 (10) | −0.0005 (10) |
C22 | 0.0267 (14) | 0.0345 (15) | 0.0273 (14) | −0.0025 (11) | 0.0034 (11) | 0.0001 (11) |
C23 | 0.0389 (16) | 0.0295 (15) | 0.0361 (16) | 0.0008 (12) | 0.0051 (13) | 0.0016 (12) |
C24 | 0.0351 (16) | 0.0420 (17) | 0.0337 (16) | 0.0126 (13) | 0.0072 (12) | 0.0068 (13) |
C25 | 0.0254 (14) | 0.0439 (17) | 0.0263 (14) | 0.0015 (12) | 0.0040 (11) | 0.0024 (12) |
C26 | 0.0269 (14) | 0.0330 (14) | 0.0217 (13) | −0.0042 (11) | 0.0048 (10) | 0.0000 (11) |
C31 | 0.0355 (16) | 0.0297 (15) | 0.0333 (15) | −0.0006 (12) | 0.0054 (12) | 0.0012 (12) |
C32 | 0.0454 (18) | 0.0360 (17) | 0.0467 (19) | −0.0059 (14) | 0.0118 (15) | 0.0005 (14) |
C33 | 0.063 (2) | 0.0407 (19) | 0.055 (2) | −0.0178 (17) | 0.0096 (18) | 0.0029 (16) |
Geometric parameters (Å, º) top
F1—C14 | 1.375 (3) | C31—C32 | 1.510 (5) |
F2—C24 | 1.367 (4) | C32—C33 | 1.522 (5) |
N1—C1 | 1.451 (4) | C1—H1A | 0.9900 |
N1—C2 | 1.474 (3) | C1—H1B | 0.9900 |
N1—C11 | 1.421 (3) | C2—H2A | 0.9900 |
N2—C2 | 1.459 (3) | C2—H2B | 0.9900 |
N2—C3 | 1.451 (4) | C3—H3A | 0.9900 |
N2—C21 | 1.422 (4) | C3—H3B | 0.9900 |
N3—C1 | 1.469 (3) | C12—H12 | 0.9500 |
N3—C3 | 1.473 (4) | C13—H13 | 0.9500 |
N3—C31 | 1.466 (4) | C15—H15 | 0.9500 |
C11—C12 | 1.393 (4) | C16—H16 | 0.9500 |
C11—C16 | 1.399 (4) | C22—H22 | 0.9500 |
C12—C13 | 1.388 (4) | C23—H23 | 0.9500 |
C13—C14 | 1.367 (4) | C25—H25 | 0.9500 |
C14—C15 | 1.376 (4) | C26—H26 | 0.9500 |
C15—C16 | 1.385 (4) | C31—H31A | 0.9900 |
C21—C22 | 1.397 (4) | C31—H31B | 0.9900 |
C21—C26 | 1.392 (4) | C32—H32A | 0.9900 |
C22—C23 | 1.385 (4) | C32—H32B | 0.9900 |
C23—C24 | 1.371 (4) | C33—H33A | 0.9800 |
C24—C25 | 1.374 (4) | C33—H33B | 0.9800 |
C25—C26 | 1.391 (4) | C33—H33C | 0.9800 |
| | | |
F2···F2i | 2.963 (3) | H1B···H12 | 2.0700 |
F1···H16ii | 2.8600 | H1B···H32A | 2.3100 |
F1···H15iii | 2.6900 | H1B···C13v | 3.0600 |
N3···C26 | 3.197 (3) | H1B···C14v | 3.0000 |
N3···C12 | 3.289 (3) | H1B···C15v | 3.1000 |
N1···H13iv | 2.8200 | H2A···C12iv | 2.9900 |
N2···H25iv | 2.8200 | H2A···H1A | 2.4500 |
N3···H12 | 2.8000 | H2A···H3B | 2.4200 |
N3···H26 | 2.6500 | H2B···C16 | 2.5700 |
C1···C14v | 3.523 (4) | H2B···C22 | 2.6100 |
C1···C13v | 3.444 (4) | H2B···H16 | 2.0900 |
C2···C13iv | 3.443 (4) | H2B···H22 | 2.1800 |
C2···C25iv | 3.566 (4) | H3A···C26 | 2.6000 |
C3···C24vi | 3.563 (4) | H3A···H26 | 2.1400 |
C3···C25vi | 3.446 (4) | H3A···H31A | 2.2800 |
C3···C26vi | 3.589 (4) | H3A···C21vi | 2.9700 |
C11···C21 | 3.326 (3) | H3A···C22vi | 2.9900 |
C12···N3 | 3.289 (3) | H3A···C23vi | 3.0900 |
C13···C2ii | 3.443 (4) | H3A···C24vi | 3.1000 |
C13···C1v | 3.444 (4) | H3A···C25vi | 3.0700 |
C14···C1v | 3.523 (4) | H3A···C26vi | 3.0200 |
C21···C11 | 3.326 (3) | H3B···H1A | 2.3600 |
C24···C3vi | 3.563 (4) | H3B···H2A | 2.4200 |
C25···C3vi | 3.446 (4) | H3B···H31B | 2.5000 |
C25···C2ii | 3.566 (4) | H3B···C24vi | 3.1000 |
C26···N3 | 3.197 (3) | H3B···C25vi | 3.0900 |
C26···C3vi | 3.589 (4) | H12···N3 | 2.8000 |
C1···H32A | 2.8800 | H12···C1 | 2.5300 |
C1···H12 | 2.5300 | H12···H1B | 2.0700 |
C2···H22 | 2.8000 | H13···N1ii | 2.8200 |
C2···H16 | 2.7400 | H13···C16ii | 3.0600 |
C3···H26 | 2.5200 | H13···H16ii | 2.5900 |
C12···H2Aii | 2.9900 | H15···F1iii | 2.6900 |
C12···H1B | 2.5800 | H15···H15iii | 2.4600 |
C13···H16ii | 3.0400 | H16···F1iv | 2.8600 |
C13···H1Bv | 3.0600 | H16···C2 | 2.7400 |
C14···H1Bv | 3.0000 | H16···C13iv | 3.0400 |
C15···H1Bv | 3.1000 | H16···H2B | 2.0900 |
C16···H2B | 2.5700 | H16···H13iv | 2.5900 |
C16···H13iv | 3.0600 | H16···H33Avii | 2.4800 |
C21···H3Avi | 2.9700 | H22···C2 | 2.8000 |
C22···H3Avi | 2.9900 | H22···C25iv | 3.0000 |
C22···H25iv | 3.0100 | H22···H2B | 2.1800 |
C22···H2B | 2.6100 | H22···H25iv | 2.5300 |
C23···H3Avi | 3.0900 | H25···N2ii | 2.8200 |
C24···H3Bvi | 3.1000 | H25···C22ii | 3.0100 |
C24···H3Avi | 3.1000 | H25···H22ii | 2.5300 |
C25···H3Avi | 3.0700 | H26···N3 | 2.6500 |
C25···H22ii | 3.0000 | H26···C3 | 2.5200 |
C25···H3Bvi | 3.0900 | H26···H3A | 2.1400 |
C26···H3A | 2.6000 | H31A···H3A | 2.2800 |
C26···H3Avi | 3.0200 | H31A···H33B | 2.4400 |
C32···H1B | 2.7500 | H31B···H1A | 2.3700 |
H1A···H2A | 2.4500 | H31B···H3B | 2.5000 |
H1A···H3B | 2.3600 | H32A···C1 | 2.8800 |
H1A···H31B | 2.3700 | H32A···H1B | 2.3100 |
H1A···H32Biv | 2.5000 | H32B···H1Aii | 2.5000 |
H1B···C12 | 2.5800 | H33A···H16viii | 2.4800 |
H1B···C32 | 2.7500 | H33B···H31A | 2.4400 |
| | | |
C1—N1—C2 | 109.4 (2) | N2—C2—H2A | 109.00 |
C1—N1—C11 | 118.2 (2) | N2—C2—H2B | 109.00 |
C2—N1—C11 | 117.5 (2) | H2A—C2—H2B | 108.00 |
C2—N2—C3 | 108.8 (2) | N2—C3—H3A | 109.00 |
C2—N2—C21 | 117.3 (2) | N2—C3—H3B | 109.00 |
C3—N2—C21 | 117.8 (2) | N3—C3—H3A | 109.00 |
C1—N3—C3 | 107.3 (2) | N3—C3—H3B | 109.00 |
C1—N3—C31 | 112.1 (2) | H3A—C3—H3B | 108.00 |
C3—N3—C31 | 110.1 (2) | C11—C12—H12 | 119.00 |
N1—C1—N3 | 111.6 (2) | C13—C12—H12 | 119.00 |
N1—C2—N2 | 112.4 (2) | C12—C13—H13 | 121.00 |
N2—C3—N3 | 112.1 (2) | C14—C13—H13 | 121.00 |
N1—C11—C12 | 123.0 (3) | C14—C15—H15 | 121.00 |
N1—C11—C16 | 119.2 (2) | C16—C15—H15 | 121.00 |
C12—C11—C16 | 117.7 (3) | C11—C16—H16 | 119.00 |
C11—C12—C13 | 121.4 (3) | C15—C16—H16 | 119.00 |
C12—C13—C14 | 118.6 (2) | C21—C22—H22 | 120.00 |
F1—C14—C13 | 118.9 (3) | C23—C22—H22 | 119.00 |
F1—C14—C15 | 118.6 (3) | C22—C23—H23 | 121.00 |
C13—C14—C15 | 122.5 (3) | C24—C23—H23 | 121.00 |
C14—C15—C16 | 118.2 (3) | C24—C25—H25 | 121.00 |
C11—C16—C15 | 121.6 (3) | C26—C25—H25 | 121.00 |
N2—C21—C22 | 119.1 (2) | C21—C26—H26 | 120.00 |
N2—C21—C26 | 122.4 (3) | C25—C26—H26 | 120.00 |
C22—C21—C26 | 118.5 (3) | N3—C31—H31A | 109.00 |
C21—C22—C23 | 121.1 (3) | N3—C31—H31B | 109.00 |
C22—C23—C24 | 118.8 (3) | C32—C31—H31A | 109.00 |
F2—C24—C23 | 119.1 (3) | C32—C31—H31B | 109.00 |
F2—C24—C25 | 118.9 (3) | H31A—C31—H31B | 108.00 |
C23—C24—C25 | 122.0 (3) | C31—C32—H32A | 109.00 |
C24—C25—C26 | 119.0 (3) | C31—C32—H32B | 109.00 |
C21—C26—C25 | 120.6 (3) | C33—C32—H32A | 109.00 |
N3—C31—C32 | 113.7 (2) | C33—C32—H32B | 109.00 |
C31—C32—C33 | 112.2 (3) | H32A—C32—H32B | 108.00 |
N1—C1—H1A | 109.00 | C32—C33—H33A | 109.00 |
N1—C1—H1B | 109.00 | C32—C33—H33B | 109.00 |
N3—C1—H1A | 109.00 | C32—C33—H33C | 109.00 |
N3—C1—H1B | 109.00 | H33A—C33—H33B | 109.00 |
H1A—C1—H1B | 108.00 | H33A—C33—H33C | 109.00 |
N1—C2—H2A | 109.00 | H33B—C33—H33C | 110.00 |
N1—C2—H2B | 109.00 | | |
| | | |
C2—N1—C1—N3 | −57.8 (3) | N1—C11—C12—C13 | 175.6 (2) |
C11—N1—C1—N3 | 80.2 (3) | C12—C11—C16—C15 | −1.1 (4) |
C11—N1—C2—N2 | −82.5 (3) | C16—C11—C12—C13 | −0.9 (4) |
C2—N1—C11—C12 | 134.9 (3) | N1—C11—C16—C15 | −177.7 (2) |
C1—N1—C2—N2 | 55.8 (3) | C11—C12—C13—C14 | 2.3 (4) |
C2—N1—C11—C16 | −48.6 (3) | C12—C13—C14—C15 | −1.9 (4) |
C1—N1—C11—C12 | 0.3 (4) | C12—C13—C14—F1 | 179.8 (2) |
C1—N1—C11—C16 | 176.8 (2) | C13—C14—C15—C16 | 0.1 (4) |
C21—N2—C3—N3 | −78.1 (3) | F1—C14—C15—C16 | 178.4 (2) |
C2—N2—C3—N3 | 58.7 (3) | C14—C15—C16—C11 | 1.5 (4) |
C3—N2—C2—N1 | −55.9 (3) | N2—C21—C22—C23 | 176.5 (2) |
C2—N2—C21—C22 | 54.9 (3) | C22—C21—C26—C25 | 2.0 (4) |
C2—N2—C21—C26 | −128.5 (3) | N2—C21—C26—C25 | −174.7 (2) |
C3—N2—C21—C26 | 4.7 (4) | C26—C21—C22—C23 | −0.3 (4) |
C21—N2—C2—N1 | 81.1 (3) | C21—C22—C23—C24 | −1.5 (4) |
C3—N2—C21—C22 | −172.0 (2) | C22—C23—C24—C25 | 1.7 (4) |
C31—N3—C1—N1 | −179.6 (2) | C22—C23—C24—F2 | −177.8 (2) |
C1—N3—C3—N2 | −60.2 (3) | F2—C24—C25—C26 | 179.5 (2) |
C3—N3—C1—N1 | 59.5 (3) | C23—C24—C25—C26 | 0.0 (4) |
C31—N3—C3—N2 | 177.6 (2) | C24—C25—C26—C21 | −1.9 (4) |
C1—N3—C31—C32 | 72.2 (3) | N3—C31—C32—C33 | 166.4 (3) |
C3—N3—C31—C32 | −168.4 (3) | | |
Symmetry codes: (i) −x, −y+3, −z; (ii) x−1, y, z; (iii) −x+1, −y+3, −z+1; (iv) x+1, y, z; (v) −x+1, −y+2, −z+1; (vi) −x+1, −y+2, −z; (vii) x+1, y+1, z; (viii) x−1, y−1, z. |