In the crystal structure of the title compound, C
18H
21F
2N
3, the triazacyclohexane ring adopts a chair conformation with an equatorial–diaxial substitution pattern; there is an equatorial arrangement of the isopropyl group and the two 2-fluorophenyl substituents are in axial positions. The packing is stabilized by weak C—H
π interactions leading to the formation of chain parallel to the
b axis.
Supporting information
CCDC reference: 627488
Key indicators
- Single-crystal X-ray study
- T = 190 K
- Mean (Wave) = 0.000 Å
- R factor = 0.044
- wR factor = 0.124
- Data-to-parameter ratio = 9.2
checkCIF/PLATON results
No syntax errors found
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.57
From the CIF: _reflns_number_total 1929
Count of symmetry unique reflns 1966
Completeness (_total/calc) 98.12%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
1 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2000); 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: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C18H21F2N3 | F(000) = 672 |
Mr = 317.38 | Dx = 1.291 Mg m−3 |
Orthorhombic, Pn21a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2ac -2n | Cell parameters from 7973 reflections |
a = 13.280 (1) Å | θ = 3.1–27.6° |
b = 13.020 (1) Å | µ = 0.09 mm−1 |
c = 9.4440 (2) Å | T = 190 K |
V = 1632.92 (18) Å3 | Prism, colourless |
Z = 4 | 0.60 × 0.33 × 0.15 mm |
Data collection top
Nonius KappaCCD diffractometer | 1812 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.6°, θmin = 3.1° |
φ scans, and ω scans with κ offsets | h = −17→15 |
7973 measured reflections | k = −10→16 |
1929 independent reflections | l = −9→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0821P)2 + 0.2864P] where P = (Fo2 + 2Fc2)/3 |
1929 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | |
C1 | 0.88974 (12) | 0.3150 (15) | 0.1544 (2) | 0.0288 (4) | |
H1A | 0.8173 | 0.3141 | 0.1410 | 0.035* | |
H1B | 0.9029 | 0.3124 | 0.2553 | 0.035* | |
C2 | 0.91700 (18) | 0.4125 (15) | −0.0548 (3) | 0.0333 (5) | |
H2A | 0.9456 | 0.4754 | −0.0925 | 0.040* | |
H2B | 0.8457 | 0.4121 | −0.0768 | 0.040* | |
C3 | 0.92145 (19) | 0.2301 (15) | −0.0651 (3) | 0.0325 (5) | |
H3A | 0.8504 | 0.2275 | −0.0885 | 0.039* | |
H3B | 0.9540 | 0.1713 | −0.1087 | 0.039* | |
C11 | 1.02810 (16) | 0.1927 (15) | 0.1397 (2) | 0.0266 (5) | |
C12 | 1.11657 (18) | 0.1898 (15) | 0.0608 (2) | 0.0310 (5) | |
H12 | 1.1156 | 0.2116 | −0.0330 | 0.037* | |
C13 | 1.20631 (19) | 0.1549 (15) | 0.1192 (3) | 0.0364 (6) | |
H13 | 1.2643 | 0.1534 | 0.0640 | 0.044* | |
C14 | 1.2105 (2) | 0.1226 (15) | 0.2580 (3) | 0.0367 (6) | |
H14 | 1.2711 | 0.1008 | 0.2971 | 0.044* | |
C15 | 1.1233 (2) | 0.1230 (15) | 0.3386 (3) | 0.0376 (6) | |
H15 | 1.1243 | 0.1009 | 0.4323 | 0.045* | |
C16 | 1.03565 (17) | 0.1566 (15) | 0.2780 (2) | 0.0320 (5) | |
C21 | 0.96364 (19) | 0.3326 (15) | −0.2785 (3) | 0.0479 (7) | |
H21 | 0.9814 | 0.4040 | −0.3001 | 0.057* | |
C31 | 1.02524 (16) | 0.4422 (15) | 0.1508 (2) | 0.0277 (5) | |
C32 | 1.11136 (19) | 0.4546 (15) | 0.0680 (3) | 0.0342 (5) | |
H32 | 1.1086 | 0.4404 | −0.0285 | 0.041* | |
C33 | 1.2012 (2) | 0.4880 (15) | 0.1279 (3) | 0.0399 (6) | |
H33 | 1.2577 | 0.4959 | 0.0708 | 0.048* | |
C34 | 1.2079 (2) | 0.5096 (15) | 0.2700 (3) | 0.0420 (6) | |
H34 | 1.2686 | 0.5309 | 0.3093 | 0.050* | |
C35 | 1.1239 (2) | 0.4993 (15) | 0.3529 (3) | 0.0432 (6) | |
H35 | 1.1269 | 0.5138 | 0.4492 | 0.052* | |
C36 | 1.03444 (19) | 0.4671 (15) | 0.2918 (2) | 0.0350 (5) | |
C211 | 1.0445 (3) | 0.2690 (15) | −0.3428 (3) | 0.0622 (9) | |
H21A | 1.0290 | 0.1976 | −0.3298 | 0.093* | |
H21B | 1.1075 | 0.2845 | −0.2979 | 0.093* | |
H21C | 1.0491 | 0.2839 | −0.4421 | 0.093* | |
C212 | 0.8614 (2) | 0.3151 (15) | −0.3462 (3) | 0.0563 (7) | |
H21D | 0.8648 | 0.3318 | −0.4451 | 0.085* | |
H21E | 0.8122 | 0.3580 | −0.3009 | 0.085* | |
H21F | 0.8425 | 0.2443 | −0.3354 | 0.085* | |
N1 | 0.93335 (14) | 0.2241 (15) | 0.0873 (2) | 0.0281 (4) | |
N2 | 0.96506 (13) | 0.3247 (15) | −0.12231 (18) | 0.0333 (4) | |
N3 | 0.93006 (14) | 0.4110 (15) | 0.0975 (2) | 0.0289 (4) | |
F16 | 0.95039 (12) | 0.1533 (15) | 0.35724 (18) | 0.0478 (5) | |
F36 | 0.95145 (13) | 0.4609 (15) | 0.37608 (16) | 0.0534 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0238 (7) | 0.0272 (9) | 0.0354 (9) | −0.0008 (10) | 0.0029 (6) | 0.0022 (10) |
C2 | 0.0364 (12) | 0.0270 (11) | 0.0365 (11) | 0.0003 (9) | −0.0064 (9) | 0.0048 (10) |
C3 | 0.0370 (13) | 0.0283 (11) | 0.0322 (11) | −0.0013 (9) | −0.0078 (9) | −0.0027 (10) |
C11 | 0.0286 (11) | 0.0194 (9) | 0.0316 (10) | −0.0002 (8) | 0.0002 (8) | −0.0003 (8) |
C12 | 0.0334 (11) | 0.0283 (10) | 0.0314 (10) | 0.0010 (10) | 0.0049 (9) | 0.0012 (9) |
C13 | 0.0299 (13) | 0.0328 (12) | 0.0467 (14) | 0.0026 (9) | 0.0067 (9) | 0.0017 (11) |
C14 | 0.0296 (13) | 0.0344 (13) | 0.0462 (13) | 0.0028 (9) | −0.0052 (10) | −0.0010 (10) |
C15 | 0.0372 (14) | 0.0402 (13) | 0.0353 (12) | 0.0013 (10) | −0.0041 (10) | 0.0058 (10) |
C16 | 0.0265 (11) | 0.0362 (11) | 0.0332 (10) | −0.0008 (9) | 0.0038 (8) | 0.0046 (10) |
C21 | 0.0575 (14) | 0.0580 (19) | 0.0281 (11) | −0.0032 (13) | −0.0041 (9) | 0.0020 (11) |
C31 | 0.0252 (11) | 0.0229 (10) | 0.0349 (10) | 0.0013 (8) | 0.0000 (8) | −0.0002 (8) |
C32 | 0.0345 (12) | 0.0312 (11) | 0.0370 (11) | −0.0023 (10) | 0.0045 (9) | −0.0020 (10) |
C33 | 0.0286 (12) | 0.0341 (13) | 0.0569 (15) | −0.0025 (9) | 0.0069 (10) | 0.0015 (11) |
C34 | 0.0301 (13) | 0.0349 (13) | 0.0611 (16) | −0.0006 (10) | −0.0126 (12) | −0.0045 (12) |
C35 | 0.0419 (15) | 0.0460 (15) | 0.0415 (13) | −0.0013 (11) | −0.0082 (11) | −0.0095 (11) |
C36 | 0.0314 (13) | 0.0364 (12) | 0.0373 (11) | −0.0026 (9) | 0.0033 (9) | −0.0060 (11) |
C211 | 0.086 (2) | 0.060 (2) | 0.0411 (16) | 0.0066 (17) | 0.0070 (14) | −0.0005 (14) |
C212 | 0.0740 (16) | 0.0584 (15) | 0.0367 (12) | −0.0083 (18) | −0.0209 (11) | 0.0042 (15) |
N1 | 0.0282 (9) | 0.0249 (9) | 0.0313 (9) | −0.0002 (7) | −0.0017 (7) | 0.0008 (7) |
N2 | 0.0395 (9) | 0.0334 (9) | 0.0270 (8) | −0.0016 (10) | −0.0039 (6) | 0.0016 (9) |
N3 | 0.0272 (9) | 0.0250 (9) | 0.0343 (9) | 0.0004 (7) | −0.0019 (7) | 0.0007 (8) |
F16 | 0.0347 (8) | 0.0694 (11) | 0.0395 (8) | 0.0060 (8) | 0.0099 (6) | 0.0202 (8) |
F36 | 0.0424 (9) | 0.0767 (12) | 0.0410 (8) | −0.0102 (9) | 0.0132 (7) | −0.0211 (9) |
Geometric parameters (Å, º) top
F16—C16 | 1.358 (3) | C34—C35 | 1.369 (5) |
F36—C36 | 1.362 (4) | C35—C36 | 1.386 (9) |
N1—C1 | 1.46 (2) | C1—H1A | 0.9700 |
N1—C3 | 1.450 (4) | C1—H1B | 0.9700 |
N1—C11 | 1.413 (8) | C2—H2A | 0.9700 |
N2—C2 | 1.46 (2) | C2—H2B | 0.9700 |
N2—C3 | 1.46 (2) | C3—H3A | 0.9700 |
N2—C21 | 1.479 (4) | C3—H3B | 0.9700 |
N3—C1 | 1.46 (2) | C12—H12 | 0.9300 |
N3—C2 | 1.449 (3) | C13—H13 | 0.9300 |
N3—C31 | 1.420 (8) | C14—H14 | 0.9300 |
C11—C12 | 1.392 (3) | C15—H15 | 0.9300 |
C11—C16 | 1.392 (10) | C21—H21 | 0.9800 |
C12—C13 | 1.390 (10) | C32—H32 | 0.9300 |
C13—C14 | 1.378 (9) | C33—H33 | 0.9300 |
C14—C15 | 1.386 (4) | C34—H34 | 0.9300 |
C15—C16 | 1.369 (9) | C35—H35 | 0.9300 |
C21—C211 | 1.486 (16) | C211—H21A | 0.9600 |
C21—C212 | 1.518 (6) | C211—H21B | 0.9600 |
C31—C32 | 1.395 (5) | C211—H21C | 0.9600 |
C31—C36 | 1.376 (7) | C212—H21D | 0.9600 |
C32—C33 | 1.390 (9) | C212—H21E | 0.9600 |
C33—C34 | 1.374 (7) | C212—H21F | 0.9600 |
| | | |
C1—N1—C3 | 110.1 (12) | N2—C2—H2B | 109.00 |
C1—N1—C11 | 115.8 (9) | N3—C2—H2A | 109.00 |
C3—N1—C11 | 117.4 (4) | N3—C2—H2B | 109.00 |
C2—N2—C3 | 109.0 (7) | H2A—C2—H2B | 108.00 |
C2—N2—C21 | 112.1 (12) | N1—C3—H3A | 109.00 |
C3—N2—C21 | 114.9 (12) | N1—C3—H3B | 109.00 |
C1—N3—C2 | 109.4 (12) | N2—C3—H3A | 109.00 |
C1—N3—C31 | 116.1 (10) | N2—C3—H3B | 109.00 |
C2—N3—C31 | 117.0 (5) | H3A—C3—H3B | 108.00 |
N1—C1—N3 | 112.8 (6) | C11—C12—H12 | 119.00 |
N2—C2—N3 | 111.8 (12) | C13—C12—H12 | 119.00 |
N1—C3—N2 | 111.6 (12) | C12—C13—H13 | 120.00 |
N1—C11—C12 | 124.9 (5) | C14—C13—H13 | 120.00 |
N1—C11—C16 | 119.4 (3) | C13—C14—H14 | 120.00 |
C12—C11—C16 | 115.6 (6) | C15—C14—H14 | 120.00 |
C11—C12—C13 | 121.4 (6) | C14—C15—H15 | 121.00 |
C12—C13—C14 | 120.8 (3) | C16—C15—H15 | 121.00 |
C13—C14—C15 | 119.2 (6) | N2—C21—H21 | 106.00 |
C14—C15—C16 | 118.8 (6) | C211—C21—H21 | 106.00 |
F16—C16—C11 | 117.9 (6) | C212—C21—H21 | 106.00 |
F16—C16—C15 | 117.9 (7) | C31—C32—H32 | 120.00 |
C11—C16—C15 | 124.2 (3) | C33—C32—H32 | 120.00 |
N2—C21—C211 | 111.1 (9) | C32—C33—H33 | 119.00 |
N2—C21—C212 | 114.9 (4) | C34—C33—H33 | 119.00 |
C211—C21—C212 | 113.0 (10) | C33—C34—H34 | 120.00 |
N3—C31—C32 | 124.4 (4) | C35—C34—H34 | 120.00 |
N3—C31—C36 | 119.3 (3) | C34—C35—H35 | 120.00 |
C32—C31—C36 | 116.3 (6) | C36—C35—H35 | 120.00 |
C31—C32—C33 | 120.8 (4) | C21—C211—H21A | 109.00 |
C32—C33—C34 | 121.1 (4) | C21—C211—H21B | 109.00 |
C33—C34—C35 | 119.1 (6) | C21—C211—H21C | 109.00 |
C34—C35—C36 | 119.3 (5) | H21A—C211—H21B | 109.00 |
F36—C36—C31 | 118.7 (6) | H21A—C211—H21C | 110.00 |
F36—C36—C35 | 117.9 (5) | H21B—C211—H21C | 109.00 |
C31—C36—C35 | 123.4 (3) | C21—C212—H21D | 110.00 |
N1—C1—H1A | 109.00 | C21—C212—H21E | 109.00 |
N1—C1—H1B | 109.00 | C21—C212—H21F | 109.00 |
N3—C1—H1A | 109.00 | H21D—C212—H21E | 109.00 |
N3—C1—H1B | 109.00 | H21D—C212—H21F | 109.00 |
H1A—C1—H1B | 108.00 | H21E—C212—H21F | 109.00 |
N2—C2—H2A | 109.00 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···CG1i | 0.97 | 2.71 | 3.493 (18) | 138 |
C3—H3B···CG2ii | 0.97 | 2.87 | 3.608 (18) | 134 |
Symmetry codes: (i) −x+2, y+1/2, −z; (ii) −x+2, y−1/2, −z. |