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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603546X/hg2080sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603546X/hg2080Isup2.hkl
Contains datablock I

CCDC reference: 624714

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

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
C18H21F2N3Z = 2
Mr = 317.38F(000) = 336
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0610 (2) ÅCell parameters from 13114 reflections
b = 10.0150 (3) Åθ = 3.0–25.8°
c = 13.5200 (4) ŵ = 0.09 mm1
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 tubeRint = 0.049
Graphite monochromatorθmax = 25.8°, θmin = 3.0°
φ scans, and ω scans with κ offsetsh = 77
13114 measured reflectionsk = 1212
3081 independent reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070H-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 reflectionsΔρmax = 0.30 e Å3
208 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
F10.1490 (3)1.37408 (18)0.49254 (14)0.0460 (6)
F20.1334 (3)1.3903 (2)0.02191 (16)0.0523 (7)
N10.6623 (4)1.0075 (2)0.33762 (16)0.0266 (7)
N20.6623 (4)1.0175 (2)0.15764 (16)0.0267 (7)
N30.4298 (4)0.8369 (2)0.23585 (16)0.0267 (7)
C10.5700 (4)0.8658 (3)0.3273 (2)0.0286 (8)
C20.7929 (4)1.0466 (3)0.25076 (19)0.0282 (8)
C30.5713 (5)0.8754 (3)0.15234 (19)0.0287 (8)
C110.5238 (4)1.0994 (3)0.37361 (18)0.0242 (8)
C120.3049 (4)1.0595 (3)0.39970 (19)0.0271 (8)
C130.1796 (4)1.1508 (3)0.4408 (2)0.0294 (8)
C140.2725 (5)1.2831 (3)0.4522 (2)0.0320 (8)
C150.4874 (5)1.3284 (3)0.4272 (2)0.0351 (9)
C160.6125 (5)1.2354 (3)0.3890 (2)0.0319 (8)
C210.5196 (4)1.1118 (3)0.12794 (18)0.0248 (8)
C220.6097 (5)1.2472 (3)0.1203 (2)0.0301 (8)
C230.4797 (5)1.3413 (3)0.0866 (2)0.0351 (9)
C240.2606 (5)1.2988 (3)0.0584 (2)0.0360 (9)
C250.1652 (5)1.1667 (3)0.0649 (2)0.0321 (9)
C260.2949 (4)1.0732 (3)0.10124 (19)0.0279 (8)
C310.3343 (5)0.6941 (3)0.2251 (2)0.0332 (9)
C320.1518 (6)0.6525 (3)0.2955 (3)0.0436 (10)
C330.0198 (7)0.5153 (3)0.2667 (3)0.0551 (11)
H1A0.693280.810700.326770.0342*
H1B0.479660.840170.384970.0342*
H2A0.923630.997530.250320.0338*
H2B0.848791.144390.256330.0338*
H3A0.482060.855080.089390.0345*
H3B0.695490.820900.152370.0345*
H120.240020.967930.389130.0324*
H130.032361.121870.460590.0353*
H150.548191.420870.435890.0422*
H160.762271.264630.372800.0382*
H220.762591.275250.138480.0361*
H230.541241.433560.083030.0421*
H250.013011.139610.044790.0385*
H260.229460.982160.107940.0335*
H31A0.273240.675430.156270.0399*
H31B0.454880.638260.236250.0399*
H32A0.219000.649300.363250.0523*
H32B0.049120.721050.296180.0523*
H33A0.096030.492250.314340.0827*
H33B0.050100.518610.200280.0827*
H33C0.120350.446830.266970.0827*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0434 (10)0.0417 (10)0.0537 (12)0.0083 (8)0.0113 (9)0.0116 (8)
F20.0467 (11)0.0510 (12)0.0640 (13)0.0211 (9)0.0027 (10)0.0153 (10)
N10.0258 (11)0.0325 (12)0.0213 (11)0.0028 (9)0.0025 (9)0.0016 (9)
N20.0259 (11)0.0330 (12)0.0209 (11)0.0023 (9)0.0023 (9)0.0012 (9)
N30.0303 (12)0.0256 (12)0.0230 (11)0.0008 (9)0.0031 (9)0.0022 (9)
C10.0286 (14)0.0305 (14)0.0267 (14)0.0034 (11)0.0038 (11)0.0034 (11)
C20.0241 (13)0.0371 (15)0.0227 (13)0.0021 (11)0.0013 (10)0.0010 (11)
C30.0307 (14)0.0330 (14)0.0224 (13)0.0027 (11)0.0055 (11)0.0016 (11)
C110.0230 (13)0.0311 (14)0.0171 (12)0.0003 (10)0.0010 (10)0.0024 (10)
C120.0246 (13)0.0314 (14)0.0230 (13)0.0030 (11)0.0017 (10)0.0031 (11)
C130.0242 (13)0.0378 (15)0.0244 (13)0.0020 (11)0.0012 (10)0.0013 (11)
C140.0322 (15)0.0354 (15)0.0281 (14)0.0045 (12)0.0005 (11)0.0036 (12)
C150.0356 (16)0.0314 (15)0.0358 (16)0.0039 (12)0.0031 (12)0.0037 (12)
C160.0256 (14)0.0355 (15)0.0322 (15)0.0041 (11)0.0043 (11)0.0001 (12)
C210.0264 (13)0.0304 (14)0.0165 (12)0.0013 (11)0.0063 (10)0.0005 (10)
C220.0267 (14)0.0345 (15)0.0273 (14)0.0025 (11)0.0034 (11)0.0001 (11)
C230.0389 (16)0.0295 (15)0.0361 (16)0.0008 (12)0.0051 (13)0.0016 (12)
C240.0351 (16)0.0420 (17)0.0337 (16)0.0126 (13)0.0072 (12)0.0068 (13)
C250.0254 (14)0.0439 (17)0.0263 (14)0.0015 (12)0.0040 (11)0.0024 (12)
C260.0269 (14)0.0330 (14)0.0217 (13)0.0042 (11)0.0048 (10)0.0000 (11)
C310.0355 (16)0.0297 (15)0.0333 (15)0.0006 (12)0.0054 (12)0.0012 (12)
C320.0454 (18)0.0360 (17)0.0467 (19)0.0059 (14)0.0118 (15)0.0005 (14)
C330.063 (2)0.0407 (19)0.055 (2)0.0178 (17)0.0096 (18)0.0029 (16)
Geometric parameters (Å, º) top
F1—C141.375 (3)C31—C321.510 (5)
F2—C241.367 (4)C32—C331.522 (5)
N1—C11.451 (4)C1—H1A0.9900
N1—C21.474 (3)C1—H1B0.9900
N1—C111.421 (3)C2—H2A0.9900
N2—C21.459 (3)C2—H2B0.9900
N2—C31.451 (4)C3—H3A0.9900
N2—C211.422 (4)C3—H3B0.9900
N3—C11.469 (3)C12—H120.9500
N3—C31.473 (4)C13—H130.9500
N3—C311.466 (4)C15—H150.9500
C11—C121.393 (4)C16—H160.9500
C11—C161.399 (4)C22—H220.9500
C12—C131.388 (4)C23—H230.9500
C13—C141.367 (4)C25—H250.9500
C14—C151.376 (4)C26—H260.9500
C15—C161.385 (4)C31—H31A0.9900
C21—C221.397 (4)C31—H31B0.9900
C21—C261.392 (4)C32—H32A0.9900
C22—C231.385 (4)C32—H32B0.9900
C23—C241.371 (4)C33—H33A0.9800
C24—C251.374 (4)C33—H33B0.9800
C25—C261.391 (4)C33—H33C0.9800
F2···F2i2.963 (3)H1B···H122.0700
F1···H16ii2.8600H1B···H32A2.3100
F1···H15iii2.6900H1B···C13v3.0600
N3···C263.197 (3)H1B···C14v3.0000
N3···C123.289 (3)H1B···C15v3.1000
N1···H13iv2.8200H2A···C12iv2.9900
N2···H25iv2.8200H2A···H1A2.4500
N3···H122.8000H2A···H3B2.4200
N3···H262.6500H2B···C162.5700
C1···C14v3.523 (4)H2B···C222.6100
C1···C13v3.444 (4)H2B···H162.0900
C2···C13iv3.443 (4)H2B···H222.1800
C2···C25iv3.566 (4)H3A···C262.6000
C3···C24vi3.563 (4)H3A···H262.1400
C3···C25vi3.446 (4)H3A···H31A2.2800
C3···C26vi3.589 (4)H3A···C21vi2.9700
C11···C213.326 (3)H3A···C22vi2.9900
C12···N33.289 (3)H3A···C23vi3.0900
C13···C2ii3.443 (4)H3A···C24vi3.1000
C13···C1v3.444 (4)H3A···C25vi3.0700
C14···C1v3.523 (4)H3A···C26vi3.0200
C21···C113.326 (3)H3B···H1A2.3600
C24···C3vi3.563 (4)H3B···H2A2.4200
C25···C3vi3.446 (4)H3B···H31B2.5000
C25···C2ii3.566 (4)H3B···C24vi3.1000
C26···N33.197 (3)H3B···C25vi3.0900
C26···C3vi3.589 (4)H12···N32.8000
C1···H32A2.8800H12···C12.5300
C1···H122.5300H12···H1B2.0700
C2···H222.8000H13···N1ii2.8200
C2···H162.7400H13···C16ii3.0600
C3···H262.5200H13···H16ii2.5900
C12···H2Aii2.9900H15···F1iii2.6900
C12···H1B2.5800H15···H15iii2.4600
C13···H16ii3.0400H16···F1iv2.8600
C13···H1Bv3.0600H16···C22.7400
C14···H1Bv3.0000H16···C13iv3.0400
C15···H1Bv3.1000H16···H2B2.0900
C16···H2B2.5700H16···H13iv2.5900
C16···H13iv3.0600H16···H33Avii2.4800
C21···H3Avi2.9700H22···C22.8000
C22···H3Avi2.9900H22···C25iv3.0000
C22···H25iv3.0100H22···H2B2.1800
C22···H2B2.6100H22···H25iv2.5300
C23···H3Avi3.0900H25···N2ii2.8200
C24···H3Bvi3.1000H25···C22ii3.0100
C24···H3Avi3.1000H25···H22ii2.5300
C25···H3Avi3.0700H26···N32.6500
C25···H22ii3.0000H26···C32.5200
C25···H3Bvi3.0900H26···H3A2.1400
C26···H3A2.6000H31A···H3A2.2800
C26···H3Avi3.0200H31A···H33B2.4400
C32···H1B2.7500H31B···H1A2.3700
H1A···H2A2.4500H31B···H3B2.5000
H1A···H3B2.3600H32A···C12.8800
H1A···H31B2.3700H32A···H1B2.3100
H1A···H32Biv2.5000H32B···H1Aii2.5000
H1B···C122.5800H33A···H16viii2.4800
H1B···C322.7500H33B···H31A2.4400
C1—N1—C2109.4 (2)N2—C2—H2A109.00
C1—N1—C11118.2 (2)N2—C2—H2B109.00
C2—N1—C11117.5 (2)H2A—C2—H2B108.00
C2—N2—C3108.8 (2)N2—C3—H3A109.00
C2—N2—C21117.3 (2)N2—C3—H3B109.00
C3—N2—C21117.8 (2)N3—C3—H3A109.00
C1—N3—C3107.3 (2)N3—C3—H3B109.00
C1—N3—C31112.1 (2)H3A—C3—H3B108.00
C3—N3—C31110.1 (2)C11—C12—H12119.00
N1—C1—N3111.6 (2)C13—C12—H12119.00
N1—C2—N2112.4 (2)C12—C13—H13121.00
N2—C3—N3112.1 (2)C14—C13—H13121.00
N1—C11—C12123.0 (3)C14—C15—H15121.00
N1—C11—C16119.2 (2)C16—C15—H15121.00
C12—C11—C16117.7 (3)C11—C16—H16119.00
C11—C12—C13121.4 (3)C15—C16—H16119.00
C12—C13—C14118.6 (2)C21—C22—H22120.00
F1—C14—C13118.9 (3)C23—C22—H22119.00
F1—C14—C15118.6 (3)C22—C23—H23121.00
C13—C14—C15122.5 (3)C24—C23—H23121.00
C14—C15—C16118.2 (3)C24—C25—H25121.00
C11—C16—C15121.6 (3)C26—C25—H25121.00
N2—C21—C22119.1 (2)C21—C26—H26120.00
N2—C21—C26122.4 (3)C25—C26—H26120.00
C22—C21—C26118.5 (3)N3—C31—H31A109.00
C21—C22—C23121.1 (3)N3—C31—H31B109.00
C22—C23—C24118.8 (3)C32—C31—H31A109.00
F2—C24—C23119.1 (3)C32—C31—H31B109.00
F2—C24—C25118.9 (3)H31A—C31—H31B108.00
C23—C24—C25122.0 (3)C31—C32—H32A109.00
C24—C25—C26119.0 (3)C31—C32—H32B109.00
C21—C26—C25120.6 (3)C33—C32—H32A109.00
N3—C31—C32113.7 (2)C33—C32—H32B109.00
C31—C32—C33112.2 (3)H32A—C32—H32B108.00
N1—C1—H1A109.00C32—C33—H33A109.00
N1—C1—H1B109.00C32—C33—H33B109.00
N3—C1—H1A109.00C32—C33—H33C109.00
N3—C1—H1B109.00H33A—C33—H33B109.00
H1A—C1—H1B108.00H33A—C33—H33C109.00
N1—C2—H2A109.00H33B—C33—H33C110.00
N1—C2—H2B109.00
C2—N1—C1—N357.8 (3)N1—C11—C12—C13175.6 (2)
C11—N1—C1—N380.2 (3)C12—C11—C16—C151.1 (4)
C11—N1—C2—N282.5 (3)C16—C11—C12—C130.9 (4)
C2—N1—C11—C12134.9 (3)N1—C11—C16—C15177.7 (2)
C1—N1—C2—N255.8 (3)C11—C12—C13—C142.3 (4)
C2—N1—C11—C1648.6 (3)C12—C13—C14—C151.9 (4)
C1—N1—C11—C120.3 (4)C12—C13—C14—F1179.8 (2)
C1—N1—C11—C16176.8 (2)C13—C14—C15—C160.1 (4)
C21—N2—C3—N378.1 (3)F1—C14—C15—C16178.4 (2)
C2—N2—C3—N358.7 (3)C14—C15—C16—C111.5 (4)
C3—N2—C2—N155.9 (3)N2—C21—C22—C23176.5 (2)
C2—N2—C21—C2254.9 (3)C22—C21—C26—C252.0 (4)
C2—N2—C21—C26128.5 (3)N2—C21—C26—C25174.7 (2)
C3—N2—C21—C264.7 (4)C26—C21—C22—C230.3 (4)
C21—N2—C2—N181.1 (3)C21—C22—C23—C241.5 (4)
C3—N2—C21—C22172.0 (2)C22—C23—C24—C251.7 (4)
C31—N3—C1—N1179.6 (2)C22—C23—C24—F2177.8 (2)
C1—N3—C3—N260.2 (3)F2—C24—C25—C26179.5 (2)
C3—N3—C1—N159.5 (3)C23—C24—C25—C260.0 (4)
C31—N3—C3—N2177.6 (2)C24—C25—C26—C211.9 (4)
C1—N3—C31—C3272.2 (3)N3—C31—C32—C33166.4 (3)
C3—N3—C31—C32168.4 (3)
Symmetry codes: (i) x, y+3, z; (ii) x1, 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) x1, y1, z.
 

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