Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the mol­ecule of the title compound, C18H21F2N3, the 1,3,5-triaza­cyclo­hexane ring has a chair conformation. Intra­molecular C—H...F and C—H...N hydrogen bonds may be effective in the stabilization of the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030601/hk2091sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030601/hk2091Isup2.hkl
Contains datablock I

CCDC reference: 624723

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.147
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,3-Bis(2-fluorophenyl)-5-propyl-1,3,5-triazacyclohexane top
Crystal data top
C18H21F2N3Z = 2
Mr = 317.38F(000) = 336
Triclinic, P1Dx = 1.318 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8130 (6) ÅCell parameters from 9398 reflections
b = 10.4780 (8) Åθ = 3.3–25.0°
c = 12.322 (1) ŵ = 0.10 mm1
α = 114.089 (4)°T = 150 K
β = 94.033 (4)°Prism, colourless
γ = 91.320 (5)°0.35 × 0.25 × 0.18 mm
V = 799.74 (11) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
2248 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.084
Graphite monochromatorθmax = 25.0°, θmin = 3.3°
φ scans, and ω scans with κ offsetsh = 88
9398 measured reflectionsk = 1212
2713 independent reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.0293P)2 + 1.3984P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2713 reflectionsΔρmax = 0.29 e Å3
208 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997)
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
F10.08403 (19)0.34061 (14)0.21481 (11)0.0501 (5)
F20.04931 (19)0.35747 (15)0.52013 (12)0.0549 (5)
N10.0499 (3)0.06474 (19)0.17821 (14)0.0378 (6)
N20.0308 (3)0.0773 (2)0.38077 (14)0.0373 (6)
N30.0756 (3)0.12759 (19)0.21859 (14)0.0382 (6)
C10.0362 (3)0.0844 (2)0.13348 (17)0.0408 (7)
C20.1401 (3)0.1164 (3)0.29267 (17)0.0398 (7)
C30.0185 (3)0.0725 (2)0.33211 (17)0.0392 (7)
C110.1150 (3)0.1460 (2)0.17147 (16)0.0358 (7)
C120.0964 (3)0.2849 (2)0.19092 (17)0.0391 (7)
C130.2461 (3)0.3699 (3)0.18409 (18)0.0438 (7)
C140.4273 (3)0.3145 (3)0.15409 (18)0.0450 (8)
C150.4519 (3)0.1759 (3)0.13012 (18)0.0439 (8)
C160.2982 (3)0.0925 (3)0.13986 (17)0.0401 (7)
C210.1448 (3)0.1613 (2)0.43833 (16)0.0361 (7)
C220.1333 (3)0.3034 (3)0.50699 (18)0.0413 (7)
C230.2935 (3)0.3933 (3)0.56357 (19)0.0483 (8)
C240.4786 (3)0.3396 (3)0.55560 (18)0.0469 (8)
C250.4965 (3)0.1983 (3)0.49354 (17)0.0430 (7)
C260.3314 (3)0.1101 (3)0.43451 (17)0.0394 (7)
C310.0794 (3)0.2801 (2)0.17206 (19)0.0445 (8)
C320.2321 (3)0.3386 (3)0.08203 (19)0.0469 (8)
C330.4428 (4)0.2968 (3)0.1386 (2)0.0532 (9)
H1A0.170730.129740.115380.0490*
H1B0.028600.117510.058070.0490*
H2A0.277710.077210.279000.0477*
H2B0.143140.219670.324790.0477*
H3A0.058020.098080.390910.0470*
H3B0.152870.117100.318580.0470*
H130.226260.465000.199630.0525*
H140.534010.371930.150090.0541*
H150.574620.136920.106760.0527*
H160.318290.002530.124720.0481*
H230.278170.490430.607380.0580*
H240.592320.400080.592790.0563*
H250.622430.160570.490920.0516*
H260.346660.012930.390770.0473*
H31A0.108820.307290.239330.0534*
H31B0.052600.322260.133420.0534*
H32A0.209830.304480.018420.0563*
H32B0.214180.442060.044460.0563*
H33A0.534810.336100.077140.0798*
H33B0.461980.194450.175060.0798*
H33C0.467070.332820.199960.0798*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0454 (8)0.0587 (9)0.0517 (8)0.0143 (6)0.0128 (6)0.0262 (7)
F20.0405 (8)0.0609 (9)0.0546 (8)0.0119 (6)0.0097 (6)0.0137 (7)
N10.0364 (10)0.0501 (11)0.0281 (8)0.0014 (8)0.0058 (7)0.0169 (8)
N20.0345 (10)0.0512 (12)0.0290 (8)0.0034 (8)0.0070 (7)0.0187 (8)
N30.0418 (10)0.0480 (11)0.0272 (8)0.0005 (8)0.0061 (7)0.0175 (8)
C10.0414 (13)0.0535 (14)0.0278 (10)0.0017 (10)0.0031 (8)0.0171 (10)
C20.0326 (11)0.0578 (14)0.0317 (10)0.0037 (10)0.0064 (8)0.0206 (10)
C30.0381 (12)0.0532 (14)0.0308 (10)0.0000 (10)0.0075 (8)0.0213 (10)
C110.0362 (11)0.0500 (14)0.0225 (9)0.0031 (9)0.0039 (8)0.0159 (9)
C120.0371 (12)0.0525 (14)0.0294 (10)0.0103 (10)0.0080 (8)0.0174 (9)
C130.0513 (14)0.0474 (13)0.0354 (11)0.0023 (11)0.0070 (9)0.0194 (10)
C140.0442 (14)0.0588 (16)0.0358 (11)0.0040 (11)0.0062 (9)0.0231 (11)
C150.0386 (12)0.0643 (16)0.0342 (11)0.0074 (11)0.0102 (9)0.0243 (11)
C160.0440 (13)0.0497 (14)0.0298 (10)0.0078 (10)0.0086 (8)0.0185 (10)
C210.0346 (11)0.0510 (14)0.0254 (9)0.0025 (9)0.0068 (8)0.0179 (9)
C220.0335 (12)0.0558 (15)0.0354 (10)0.0077 (10)0.0093 (8)0.0184 (10)
C230.0492 (14)0.0522 (15)0.0389 (12)0.0010 (11)0.0078 (10)0.0135 (10)
C240.0410 (13)0.0608 (16)0.0341 (11)0.0039 (11)0.0036 (9)0.0149 (11)
C250.0340 (12)0.0648 (16)0.0313 (10)0.0067 (10)0.0060 (8)0.0203 (10)
C260.0415 (12)0.0500 (13)0.0281 (10)0.0073 (10)0.0068 (8)0.0167 (9)
C310.0486 (14)0.0494 (14)0.0377 (11)0.0011 (10)0.0065 (9)0.0198 (10)
C320.0591 (15)0.0489 (14)0.0338 (11)0.0048 (11)0.0083 (10)0.0173 (10)
C330.0533 (15)0.0641 (17)0.0470 (13)0.0072 (12)0.0127 (10)0.0261 (12)
Geometric parameters (Å, º) top
F1—C121.372 (2)C31—C321.525 (3)
F2—C221.372 (3)C32—C331.523 (3)
N1—C11.437 (3)C1—H1A0.9900
N1—C21.474 (3)C1—H1B0.9900
N1—C111.422 (3)C2—H2A0.9900
N2—C21.471 (3)C2—H2B0.9900
N2—C31.441 (3)C3—H3A0.9900
N2—C211.425 (3)C3—H3B0.9900
N3—C11.475 (3)C13—H130.9500
N3—C31.478 (3)C14—H140.9500
N3—C311.463 (3)C15—H150.9500
C11—C121.386 (3)C16—H160.9500
C11—C161.395 (3)C23—H230.9500
C12—C131.368 (3)C24—H240.9500
C13—C141.386 (3)C25—H250.9500
C14—C151.376 (5)C26—H260.9500
C15—C161.391 (4)C31—H31A0.9900
C21—C221.388 (4)C31—H31B0.9900
C21—C261.388 (3)C32—H32A0.9900
C22—C231.369 (3)C32—H32B0.9900
C23—C241.386 (3)C33—H33A0.9800
C24—C251.374 (4)C33—H33B0.9800
C25—C261.392 (3)C33—H33C0.9800
F1···N12.756 (3)H1A···H31B2.2800
F1···C22.904 (4)H1B···C162.6400
F1···C14i3.341 (2)H1B···C322.8300
F2···C24i3.288 (2)H1B···H162.2100
F2···N22.741 (3)H1B···H32A2.2400
F2···C22.920 (3)H1B···C11iii2.8200
F1···H2B2.2500H1B···C12iii2.9000
F1···H14i2.7300H2A···C15i3.0000
F1···H23ii2.6500H2A···C25i2.9800
F1···H32Aiii2.8100H2A···H1A2.4500
F2···H2B2.2800H2A···H3B2.4400
F2···H24i2.6400H2A···H15i2.5900
N1···F12.756 (3)H2A···H25i2.5400
N2···F22.741 (3)H2B···F12.2500
N3···C263.171 (3)H2B···F22.2800
N3···C163.230 (4)H2B···C122.6600
N1···H15i2.8600H2B···C222.6600
N2···H3Aiv2.7500H3A···C262.6900
N2···H25i2.7900H3A···H262.2600
N3···H162.6800H3A···H31A2.2800
N3···H262.6200H3A···N2iv2.7500
N3···H33B2.7700H3A···C21iv2.8800
C1···C11iii3.542 (3)H3B···H1A2.4500
C2···F12.904 (4)H3B···H2A2.4400
C2···F22.920 (3)H3B···H31B2.5600
C2···C25i3.496 (3)H13···C31x3.0100
C2···C15i3.528 (3)H13···C32x2.9600
C3···C21iv3.473 (3)H13···H31Ax2.4000
C11···C1iii3.542 (3)H13···H32Bx2.4700
C11···C213.218 (3)H13···H24vi2.5700
C14···F1v3.341 (2)H14···F1v2.7300
C15···C2v3.528 (3)H15···N1v2.8600
C16···C263.550 (3)H15···C2v2.9800
C16···N33.230 (4)H15···H2Av2.5900
C21···C113.218 (3)H16···N32.6800
C21···C3iv3.473 (3)H16···C12.5700
C24···F2v3.288 (2)H16···H1B2.2100
C25···C2v3.496 (3)H16···H33B2.5300
C26···N33.171 (3)H23···F1ii2.6500
C26···C163.550 (3)H24···F2v2.6400
C1···H162.5700H24···C13vi2.9400
C1···H32A2.8300H24···H13vi2.5700
C2···H25i2.9100H25···N2v2.7900
C2···H15i2.9800H25···C2v2.9100
C3···H262.5700H25···H2Av2.5400
C11···H1Biii2.8200H26···N32.6200
C12···H1Biii2.9000H26···C32.5700
C12···H2B2.6600H26···H3A2.2600
C13···H24vi2.9400H31A···H3A2.2800
C14···H33Avii2.9800H31A···H13ix2.4000
C15···H2Av3.0000H31A···H33C2.5200
C16···H1B2.6400H31B···H1A2.2800
C21···H3Aiv2.8800H31B···H3B2.5600
C22···H2B2.6600H32A···C12.8300
C24···H33Cviii3.0400H32A···H1B2.2400
C25···H2Av2.9800H32A···F1iii2.8100
C26···H3A2.6900H32B···H13ix2.4700
C31···H13ix3.0100H33A···C14vii2.9800
C32···H1B2.8300H33B···N32.7700
C32···H13ix2.9600H33B···H162.5300
H1A···H2A2.4500H33C···H31A2.5200
H1A···H3B2.4500H33C···C24viii3.0400
C1—N1—C2109.7 (2)N2—C2—H2A109.00
C1—N1—C11117.99 (18)N2—C2—H2B109.00
C2—N1—C11116.51 (18)H2A—C2—H2B108.00
C2—N2—C3109.36 (17)N2—C3—H3A109.00
C2—N2—C21115.3 (2)N2—C3—H3B109.00
C3—N2—C21117.53 (19)N3—C3—H3A109.00
C1—N3—C3108.29 (17)N3—C3—H3B109.00
C1—N3—C31111.11 (16)H3A—C3—H3B108.00
C3—N3—C31110.18 (18)C12—C13—H13121.00
N1—C1—N3112.71 (16)C14—C13—H13121.00
N1—C2—N2111.80 (19)C13—C14—H14120.00
N2—C3—N3112.67 (18)C15—C14—H14120.00
N1—C11—C12120.11 (19)C14—C15—H15120.00
N1—C11—C16123.8 (2)C16—C15—H15120.00
C12—C11—C16116.1 (2)C11—C16—H16119.00
F1—C12—C11118.61 (19)C15—C16—H16119.00
F1—C12—C13117.4 (2)C22—C23—H23121.00
C11—C12—C13124.0 (2)C24—C23—H23121.00
C12—C13—C14118.7 (3)C23—C24—H24120.00
C13—C14—C15119.7 (2)C25—C24—H24120.00
C14—C15—C16120.4 (2)C24—C25—H25120.00
C11—C16—C15121.1 (3)C26—C25—H25120.00
N2—C21—C22119.54 (19)C21—C26—H26119.00
N2—C21—C26124.4 (2)C25—C26—H26119.00
C22—C21—C26116.0 (2)N3—C31—H31A109.00
F2—C22—C21118.3 (2)N3—C31—H31B109.00
F2—C22—C23117.7 (2)C32—C31—H31A109.00
C21—C22—C23124.0 (2)C32—C31—H31B109.00
C22—C23—C24118.6 (3)H31A—C31—H31B108.00
C23—C24—C25119.6 (2)C31—C32—H32A109.00
C24—C25—C26120.5 (2)C31—C32—H32B109.00
C21—C26—C25121.3 (3)C33—C32—H32A109.00
N3—C31—C32112.6 (2)C33—C32—H32B109.00
C31—C32—C33112.67 (18)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—H33C110.00
N1—C2—H2A109.00H33B—C33—H33C109.00
N1—C2—H2B109.00
C2—N1—C1—N356.9 (2)N1—C11—C12—F11.0 (3)
C11—N1—C1—N379.8 (2)C16—C11—C12—F1175.92 (16)
C11—N1—C2—N281.1 (3)N1—C11—C12—C13178.77 (18)
C2—N1—C11—C1259.0 (3)N1—C11—C16—C15177.38 (18)
C1—N1—C2—N256.3 (2)C16—C11—C12—C131.9 (3)
C2—N1—C11—C16124.4 (2)C11—C12—C13—C141.1 (3)
C1—N1—C11—C12167.22 (17)F1—C12—C13—C14176.75 (17)
C1—N1—C11—C169.4 (3)C12—C13—C14—C151.0 (3)
C21—N2—C3—N376.6 (2)C13—C14—C15—C162.2 (3)
C3—N2—C21—C2610.5 (3)C14—C15—C16—C111.4 (3)
C3—N2—C2—N156.4 (3)N2—C21—C26—C25179.6 (2)
C21—N2—C2—N178.7 (3)N2—C21—C22—F22.1 (3)
C2—N2—C3—N357.4 (2)N2—C21—C22—C23178.5 (2)
C2—N2—C21—C26120.8 (2)C26—C21—C22—C233.7 (4)
C2—N2—C21—C2261.6 (3)C26—C21—C22—F2175.8 (2)
C3—N2—C21—C22167.08 (19)C22—C21—C26—C251.9 (3)
C1—N3—C3—N256.9 (2)F2—C22—C23—C24177.3 (2)
C31—N3—C3—N2178.56 (17)C21—C22—C23—C242.2 (4)
C31—N3—C1—N1177.65 (17)C22—C23—C24—C251.2 (4)
C3—N3—C1—N156.5 (2)C23—C24—C25—C262.8 (4)
C3—N3—C31—C32160.20 (17)C24—C25—C26—C211.2 (4)
C1—N3—C31—C3279.8 (2)N3—C31—C32—C3367.5 (3)
C12—C11—C16—C150.6 (3)
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z+1; (iii) x, y, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) x+1, y+1, z+1; (vii) x+1, y, z; (viii) x+1, y, z+1; (ix) x, y1, z; (x) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···F10.99002.25002.904 (4)123.00
C2—H2B···F20.99002.28002.920 (3)121.00
C26—H26···N30.95002.62003.171 (3)118.00
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds