J147 [N-(2,4-dimethylphenyl)-2,2,2-trifluoro-N′-(3-methoxybenzylidene)acetohydrazide] has recently been reported as a promising new drug for the treatment of Alzheimer's disease. The X-ray structures of seven new 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles, namely 1-(3,4-dimethylphenyl)-4-phenyl-5-trifluoromethyl-1H-1,2,3-triazole (C17H14F3N3, 1), 1-(3,4-dimethylphenyl)-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H16F3N3O, 2), 1-(3,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H16F3N3O, 3), 1-(2,4-dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H16F3N3O, 4), 1-[2,4-bis(trifluoromethyl)phenyl]-4-(3-methoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C18H10F9N3O, 5), 1-(3,4-dimethoxyphenyl)-4-(3,4-dimethoxyphenyl)-5-trifluoromethyl-1H-1,2,3-triazole (C19H18F3N3O4, 6) and 3-[4-(3,4-dimethoxyphenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenol (C17H14F3N3O3, 7), have been determined and compared to that of J147. B3LYP/6-311++G(d,p) calculations have been performed to determine the potential surface and molecular electrostatic potential (MEP) of J147, and to examine the correlation between hydrazone J147 and the 1,2,3-triazoles, both bearing a CF3 substituent. Using MEPs, it was found that the minimum-energy conformation of 4, which is nearly identical to its X-ray structure, is closely related to one of the J147 seven minima.
Supporting information
CCDC references: 1590422; 1590421; 1826637; 1590419; 1590418; 1590417; 1590416
Data collection: CrysAlis PRO (Agilent, 2013) for 1_triazol34; SAINT (Bruker, 2002) for 2_C18H16F3N3O_3OMe34, 3_C18H16F3N3O_4OMe34, 5_C18H10F9N3O_abc13, 6_C19H18F3N3O4_ABC23, 7_C17H14F3N3O3; SMART (Bruker, 2002) for 4_4OMe24Me. Cell refinement: CrysAlis PRO (Agilent, 2013) for 1_triazol34; SMART (Bruker, 2002) for 2_C18H16F3N3O_3OMe34, 3_C18H16F3N3O_4OMe34, 4_4OMe24Me, 5_C18H10F9N3O_abc13, 6_C19H18F3N3O4_ABC23, 7_C17H14F3N3O3. Data reduction: CrysAlis PRO (Agilent, 2013) for 1_triazol34; SAINT (Bruker, 2002) for 2_C18H16F3N3O_3OMe34, 3_C18H16F3N3O_4OMe34, 4_4OMe24Me, 5_C18H10F9N3O_abc13, 6_C19H18F3N3O4_ABC23, 7_C17H14F3N3O3. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for 1_triazol34, 2_C18H16F3N3O_3OMe34, 4_4OMe24Me, 5_C18H10F9N3O_abc13, 7_C17H14F3N3O3. For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
1-(3,4-Dimethylphenyl)-4-phenyl-5-trifluoromethyl-1
H-1,2,3-triazole (1_triazol34)
top
Crystal data top
C17H14F3N3 | F(000) = 1312 |
Mr = 317.31 | Dx = 1.346 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.001 (8) Å | Cell parameters from 2404 reflections |
b = 20.82 (2) Å | θ = 2.7–21.1° |
c = 15.124 (7) Å | µ = 0.11 mm−1 |
β = 96.12 (5)° | T = 296 K |
V = 3131 (5) Å3 | Needle, colourless |
Z = 8 | 0.46 × 0.12 × 0.07 mm |
Data collection top
Agilent Xcalibur Atlas CCD diffractometer | 2879 reflections with I > 2σ(I) |
ω scans | Rint = 0.045 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | θmax = 25.0°, θmin = 2.3° |
Tmin = 0.859, Tmax = 1.000 | h = −11→11 |
14744 measured reflections | k = −24→15 |
5504 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.037P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5504 reflections | Δρmax = 0.15 e Å−3 |
447 parameters | Δρmin = −0.22 e Å−3 |
36 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F11 | 0.42912 (15) | 0.08479 (9) | 0.68419 (10) | 0.0856 (6) | |
F21 | 0.45733 (15) | 0.06191 (9) | 0.82172 (9) | 0.0839 (6) | |
F31 | 0.58601 (17) | 0.02044 (9) | 0.73286 (11) | 0.0852 (5) | |
N11 | 0.6481 (2) | 0.17013 (11) | 0.70246 (12) | 0.0528 (6) | |
N21 | 0.7302 (2) | 0.21710 (12) | 0.73692 (13) | 0.0688 (7) | |
N31 | 0.7509 (2) | 0.20703 (12) | 0.82346 (13) | 0.0650 (7) | |
C41 | 0.6827 (2) | 0.15327 (13) | 0.84497 (14) | 0.0474 (6) | |
C51 | 0.6154 (2) | 0.12982 (13) | 0.76785 (14) | 0.0453 (6) | |
C61 | 0.5227 (3) | 0.07490 (16) | 0.75157 (16) | 0.0578 (8) | |
C71 | 0.6910 (2) | 0.13053 (14) | 0.93810 (14) | 0.0474 (7) | |
C81 | 0.7027 (2) | 0.17509 (14) | 1.00691 (14) | 0.0578 (7) | |
H81 | 0.7046 | 0.2188 | 0.9943 | 0.069* | |
C91 | 0.7117 (3) | 0.15420 (16) | 1.09445 (16) | 0.0696 (9) | |
H91 | 0.7201 | 0.1841 | 1.1404 | 0.084* | |
C101 | 0.7084 (3) | 0.08990 (17) | 1.11375 (17) | 0.0720 (9) | |
H101 | 0.7129 | 0.0763 | 1.1726 | 0.086* | |
C111 | 0.6985 (3) | 0.04554 (15) | 1.04609 (17) | 0.0732 (9) | |
H111 | 0.6969 | 0.0019 | 1.0591 | 0.088* | |
C121 | 0.6909 (3) | 0.06582 (15) | 0.95877 (16) | 0.0605 (8) | |
H121 | 0.6857 | 0.0356 | 0.9133 | 0.073* | |
C131 | 0.6151 (2) | 0.16775 (14) | 0.60726 (14) | 0.0506 (7) | |
C141 | 0.6584 (3) | 0.11626 (14) | 0.56026 (15) | 0.0594 (7) | |
H141 | 0.7049 | 0.0829 | 0.5907 | 0.071* | |
C151 | 0.6335 (3) | 0.11360 (15) | 0.46829 (16) | 0.0606 (8) | |
C161 | 0.5621 (3) | 0.16355 (16) | 0.42371 (15) | 0.0597 (8) | |
C171 | 0.5198 (3) | 0.21443 (16) | 0.47268 (16) | 0.0681 (9) | |
H171 | 0.4729 | 0.2480 | 0.4429 | 0.082* | |
C181 | 0.5450 (3) | 0.21710 (15) | 0.56441 (16) | 0.0646 (8) | |
H181 | 0.5150 | 0.2516 | 0.5961 | 0.078* | |
C191 | 0.6868 (4) | 0.05717 (17) | 0.41909 (18) | 0.1046 (12) | |
H19D | 0.7449 | 0.0726 | 0.3772 | 0.157* | |
H19E | 0.6129 | 0.0342 | 0.3881 | 0.157* | |
H19F | 0.7363 | 0.0290 | 0.4609 | 0.157* | |
C201 | 0.5346 (3) | 0.16413 (17) | 0.32280 (15) | 0.0869 (11) | |
H20D | 0.4949 | 0.1240 | 0.3028 | 0.130* | |
H20E | 0.6176 | 0.1702 | 0.2972 | 0.130* | |
H20F | 0.4741 | 0.1986 | 0.3047 | 0.130* | |
N12 | 1.1457 (2) | 0.16125 (11) | 0.69086 (12) | 0.0547 (6) | |
N22 | 1.2317 (2) | 0.20708 (12) | 0.72382 (14) | 0.0744 (7) | |
N32 | 1.2519 (2) | 0.19872 (12) | 0.81027 (13) | 0.0710 (7) | |
C42 | 1.1791 (2) | 0.14733 (13) | 0.83428 (15) | 0.0502 (7) | |
C52 | 1.1122 (2) | 0.12240 (13) | 0.75798 (15) | 0.0481 (7) | |
C62 | 1.0304 (3) | 0.06363 (16) | 0.74120 (18) | 0.0575 (8) | |
C72 | 1.1848 (3) | 0.12982 (13) | 0.92950 (15) | 0.0502 (7) | |
C82 | 1.3046 (3) | 0.13797 (14) | 0.98363 (15) | 0.0624 (8) | |
H82 | 1.3806 | 0.1529 | 0.9596 | 0.075* | |
C92 | 1.3110 (3) | 0.12394 (16) | 1.07320 (17) | 0.0809 (10) | |
H92 | 1.3912 | 0.1298 | 1.1094 | 0.097* | |
C102 | 1.1990 (4) | 0.10122 (18) | 1.10928 (19) | 0.0901 (11) | |
H102 | 1.2041 | 0.0913 | 1.1695 | 0.108* | |
C112 | 1.0816 (3) | 0.09340 (18) | 1.0568 (2) | 0.0875 (11) | |
H112 | 1.0061 | 0.0784 | 1.0813 | 0.105* | |
C122 | 1.0731 (3) | 0.10753 (15) | 0.96716 (17) | 0.0698 (9) | |
H122 | 0.9919 | 0.1021 | 0.9318 | 0.084* | |
C132 | 1.0998 (3) | 0.16084 (13) | 0.59666 (15) | 0.0512 (7) | |
C142 | 1.1766 (3) | 0.13100 (14) | 0.53780 (15) | 0.0591 (8) | |
H142 | 1.2562 | 0.1106 | 0.5594 | 0.071* | |
C152 | 1.1370 (3) | 0.13094 (14) | 0.44753 (15) | 0.0573 (7) | |
C162 | 1.0183 (3) | 0.16287 (14) | 0.41608 (15) | 0.0556 (7) | |
C172 | 0.9446 (3) | 0.19259 (15) | 0.47672 (17) | 0.0641 (8) | |
H172 | 0.8658 | 0.2138 | 0.4557 | 0.077* | |
C182 | 0.9832 (3) | 0.19211 (14) | 0.56720 (16) | 0.0592 (8) | |
H182 | 0.9316 | 0.2123 | 0.6067 | 0.071* | |
C192 | 1.2217 (3) | 0.09732 (18) | 0.38449 (16) | 0.0876 (11) | |
H19A | 1.3009 | 0.0800 | 0.4174 | 0.131* | |
H19B | 1.2473 | 0.1275 | 0.3414 | 0.131* | |
H19C | 1.1706 | 0.0631 | 0.3547 | 0.131* | |
C202 | 0.9720 (3) | 0.16489 (16) | 0.31767 (15) | 0.0827 (10) | |
H20A | 0.8882 | 0.1876 | 0.3081 | 0.124* | |
H20B | 0.9601 | 0.1219 | 0.2954 | 0.124* | |
H20C | 1.0383 | 0.1865 | 0.2870 | 0.124* | |
F12A | 1.0336 (15) | 0.0375 (4) | 0.6609 (5) | 0.103 (3) | 0.66 (3) |
F22A | 0.8992 (10) | 0.0729 (7) | 0.7457 (10) | 0.107 (3) | 0.66 (3) |
F32A | 1.0656 (14) | 0.0176 (6) | 0.7983 (10) | 0.100 (3) | 0.66 (3) |
F12B | 0.914 (2) | 0.0751 (12) | 0.708 (2) | 0.114 (7) | 0.34 (3) |
F22B | 1.016 (4) | 0.0322 (16) | 0.813 (2) | 0.120 (8) | 0.34 (3) |
F32B | 1.091 (3) | 0.0270 (9) | 0.690 (2) | 0.127 (7) | 0.34 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F11 | 0.0735 (10) | 0.1017 (16) | 0.0738 (10) | −0.0230 (10) | −0.0278 (8) | 0.0097 (10) |
F21 | 0.0792 (11) | 0.1035 (17) | 0.0699 (10) | −0.0329 (10) | 0.0121 (9) | 0.0038 (9) |
F31 | 0.0955 (13) | 0.0521 (13) | 0.1063 (13) | −0.0073 (10) | 0.0024 (10) | −0.0199 (10) |
N11 | 0.0615 (14) | 0.0521 (17) | 0.0430 (12) | −0.0079 (12) | −0.0023 (10) | −0.0035 (11) |
N21 | 0.0935 (18) | 0.0613 (19) | 0.0499 (13) | −0.0245 (15) | −0.0006 (12) | −0.0035 (12) |
N31 | 0.0840 (17) | 0.0622 (19) | 0.0470 (13) | −0.0191 (14) | −0.0012 (11) | −0.0075 (12) |
C41 | 0.0502 (15) | 0.0459 (19) | 0.0451 (14) | −0.0015 (14) | 0.0012 (12) | −0.0024 (13) |
C51 | 0.0468 (14) | 0.0469 (18) | 0.0412 (13) | 0.0000 (13) | 0.0002 (12) | −0.0034 (13) |
C61 | 0.0589 (18) | 0.063 (2) | 0.0500 (15) | −0.0063 (17) | −0.0041 (14) | −0.0021 (15) |
C71 | 0.0491 (15) | 0.049 (2) | 0.0426 (14) | 0.0034 (14) | −0.0003 (11) | −0.0037 (13) |
C81 | 0.0705 (18) | 0.054 (2) | 0.0482 (15) | 0.0064 (15) | 0.0015 (13) | −0.0065 (14) |
C91 | 0.096 (2) | 0.069 (3) | 0.0423 (15) | 0.0120 (19) | 0.0024 (14) | −0.0113 (15) |
C101 | 0.097 (2) | 0.071 (3) | 0.0471 (16) | 0.013 (2) | 0.0053 (15) | 0.0061 (17) |
C111 | 0.101 (2) | 0.055 (2) | 0.0612 (18) | 0.0097 (18) | 0.0002 (16) | 0.0068 (17) |
C121 | 0.0771 (19) | 0.052 (2) | 0.0496 (15) | 0.0101 (16) | −0.0040 (13) | −0.0075 (14) |
C131 | 0.0584 (17) | 0.054 (2) | 0.0386 (13) | −0.0041 (15) | −0.0009 (12) | −0.0012 (14) |
C141 | 0.0719 (18) | 0.052 (2) | 0.0516 (15) | 0.0029 (15) | −0.0055 (13) | −0.0007 (14) |
C151 | 0.0677 (18) | 0.063 (2) | 0.0506 (16) | −0.0058 (16) | 0.0025 (14) | −0.0086 (15) |
C161 | 0.0612 (18) | 0.073 (2) | 0.0445 (14) | −0.0115 (17) | 0.0023 (13) | 0.0003 (16) |
C171 | 0.081 (2) | 0.068 (2) | 0.0537 (17) | 0.0094 (18) | −0.0030 (15) | 0.0118 (16) |
C181 | 0.083 (2) | 0.060 (2) | 0.0499 (16) | 0.0093 (17) | 0.0013 (14) | 0.0008 (15) |
C191 | 0.147 (3) | 0.093 (3) | 0.073 (2) | 0.016 (3) | 0.005 (2) | −0.032 (2) |
C201 | 0.094 (2) | 0.121 (3) | 0.0449 (15) | −0.019 (2) | 0.0031 (15) | 0.0051 (17) |
N12 | 0.0667 (14) | 0.0497 (17) | 0.0461 (12) | −0.0061 (12) | −0.0017 (11) | 0.0068 (11) |
N22 | 0.1057 (19) | 0.0608 (19) | 0.0535 (14) | −0.0314 (16) | −0.0068 (13) | 0.0044 (13) |
N32 | 0.1008 (19) | 0.0614 (19) | 0.0485 (13) | −0.0240 (15) | −0.0032 (12) | 0.0044 (12) |
C42 | 0.0542 (16) | 0.0463 (19) | 0.0497 (15) | −0.0010 (14) | 0.0035 (12) | 0.0043 (13) |
C52 | 0.0503 (15) | 0.0439 (18) | 0.0489 (14) | −0.0021 (14) | 0.0000 (12) | 0.0065 (14) |
C62 | 0.063 (2) | 0.057 (2) | 0.0503 (18) | −0.0059 (18) | −0.0008 (17) | 0.0072 (17) |
C72 | 0.0587 (17) | 0.0447 (19) | 0.0474 (14) | 0.0058 (14) | 0.0071 (13) | 0.0005 (13) |
C82 | 0.0664 (19) | 0.068 (2) | 0.0526 (16) | −0.0019 (16) | 0.0046 (14) | −0.0053 (14) |
C92 | 0.097 (2) | 0.092 (3) | 0.0508 (17) | 0.007 (2) | −0.0055 (16) | −0.0061 (17) |
C102 | 0.129 (3) | 0.095 (3) | 0.0486 (18) | 0.022 (3) | 0.019 (2) | 0.0097 (18) |
C112 | 0.094 (3) | 0.103 (3) | 0.071 (2) | 0.011 (2) | 0.0340 (19) | 0.019 (2) |
C122 | 0.0626 (19) | 0.081 (3) | 0.0661 (18) | 0.0058 (17) | 0.0096 (15) | 0.0101 (16) |
C132 | 0.0591 (17) | 0.0470 (19) | 0.0459 (14) | −0.0036 (15) | −0.0021 (13) | 0.0076 (13) |
C142 | 0.0598 (17) | 0.063 (2) | 0.0517 (16) | 0.0102 (15) | −0.0068 (13) | 0.0039 (14) |
C152 | 0.0571 (17) | 0.062 (2) | 0.0520 (15) | 0.0008 (15) | −0.0001 (13) | 0.0013 (14) |
C162 | 0.0619 (17) | 0.055 (2) | 0.0474 (14) | −0.0058 (15) | −0.0055 (13) | 0.0053 (14) |
C172 | 0.0580 (17) | 0.065 (2) | 0.0655 (17) | 0.0067 (16) | −0.0091 (14) | 0.0071 (16) |
C182 | 0.0600 (17) | 0.060 (2) | 0.0577 (16) | 0.0037 (16) | 0.0050 (14) | 0.0015 (15) |
C192 | 0.079 (2) | 0.120 (3) | 0.0635 (17) | 0.012 (2) | 0.0055 (15) | −0.0206 (19) |
C202 | 0.090 (2) | 0.095 (3) | 0.0578 (17) | 0.002 (2) | −0.0149 (15) | 0.0055 (17) |
F12A | 0.149 (7) | 0.094 (4) | 0.068 (3) | −0.063 (4) | 0.028 (3) | −0.021 (3) |
F22A | 0.058 (3) | 0.101 (6) | 0.166 (8) | −0.015 (3) | 0.023 (5) | −0.014 (6) |
F32A | 0.120 (6) | 0.055 (4) | 0.113 (8) | −0.020 (3) | −0.042 (5) | 0.033 (4) |
F12B | 0.049 (8) | 0.115 (10) | 0.166 (15) | −0.031 (8) | −0.041 (9) | 0.046 (12) |
F22B | 0.17 (2) | 0.092 (15) | 0.084 (6) | −0.065 (12) | −0.020 (13) | 0.040 (10) |
F32B | 0.127 (12) | 0.073 (7) | 0.189 (16) | −0.027 (7) | 0.050 (11) | −0.082 (9) |
Geometric parameters (Å, º) top
F11—C61 | 1.324 (3) | N12—C132 | 1.449 (3) |
F21—C61 | 1.332 (3) | N22—N32 | 1.313 (3) |
F31—C61 | 1.343 (3) | N32—C42 | 1.365 (3) |
N11—N21 | 1.345 (3) | C42—C52 | 1.373 (3) |
N11—C51 | 1.363 (3) | C42—C72 | 1.481 (3) |
N11—C131 | 1.443 (3) | C52—C62 | 1.479 (4) |
N21—N31 | 1.320 (3) | C62—F12A | 1.334 (7) |
N31—C41 | 1.368 (3) | C62—F22A | 1.335 (10) |
C41—C51 | 1.373 (3) | C62—F32A | 1.313 (14) |
C41—C71 | 1.480 (3) | C62—F12B | 1.236 (18) |
C51—C61 | 1.476 (4) | C62—F22B | 1.29 (3) |
C71—C81 | 1.390 (3) | C62—F32B | 1.280 (14) |
C71—C121 | 1.383 (4) | C72—C82 | 1.388 (3) |
C81—H81 | 0.9300 | C72—C122 | 1.387 (3) |
C81—C91 | 1.387 (3) | C82—H82 | 0.9300 |
C91—H91 | 0.9300 | C82—C92 | 1.381 (3) |
C91—C101 | 1.371 (4) | C92—H92 | 0.9300 |
C101—H101 | 0.9300 | C92—C102 | 1.381 (4) |
C101—C111 | 1.374 (4) | C102—H102 | 0.9300 |
C111—H111 | 0.9300 | C102—C112 | 1.355 (4) |
C111—C121 | 1.381 (3) | C112—H112 | 0.9300 |
C121—H121 | 0.9300 | C112—C122 | 1.381 (3) |
C131—C141 | 1.381 (4) | C122—H122 | 0.9300 |
C131—C181 | 1.367 (4) | C132—C142 | 1.383 (3) |
C141—H141 | 0.9300 | C132—C182 | 1.369 (3) |
C141—C151 | 1.388 (3) | C142—H142 | 0.9300 |
C151—C161 | 1.394 (4) | C142—C152 | 1.380 (3) |
C151—C191 | 1.517 (4) | C152—C162 | 1.399 (4) |
C161—C171 | 1.384 (4) | C152—C192 | 1.513 (3) |
C161—C201 | 1.522 (3) | C162—C172 | 1.382 (3) |
C171—H171 | 0.9300 | C162—C202 | 1.511 (3) |
C171—C181 | 1.384 (3) | C172—H172 | 0.9300 |
C181—H181 | 0.9300 | C172—C182 | 1.382 (3) |
C191—H19D | 0.9600 | C182—H182 | 0.9300 |
C191—H19E | 0.9600 | C192—H19A | 0.9600 |
C191—H19F | 0.9600 | C192—H19B | 0.9600 |
C201—H20D | 0.9600 | C192—H19C | 0.9600 |
C201—H20E | 0.9600 | C202—H20A | 0.9600 |
C201—H20F | 0.9600 | C202—H20B | 0.9600 |
N12—N22 | 1.344 (3) | C202—H20C | 0.9600 |
N12—C52 | 1.367 (3) | | |
| | | |
N21—N11—C51 | 110.48 (19) | N32—N22—N12 | 107.5 (2) |
N21—N11—C131 | 118.5 (2) | N22—N32—C42 | 109.8 (2) |
C51—N11—C131 | 131.0 (2) | N32—C42—C52 | 107.4 (2) |
N31—N21—N11 | 107.1 (2) | N32—C42—C72 | 119.0 (2) |
N21—N31—C41 | 109.6 (2) | C52—C42—C72 | 133.6 (3) |
N31—C41—C51 | 107.5 (2) | N12—C52—C42 | 105.3 (2) |
N31—C41—C71 | 120.6 (2) | N12—C52—C62 | 122.5 (2) |
C51—C41—C71 | 131.9 (3) | C42—C52—C62 | 131.9 (2) |
N11—C51—C41 | 105.3 (2) | F12A—C62—C52 | 115.3 (4) |
N11—C51—C61 | 123.4 (2) | F12A—C62—F22A | 102.9 (6) |
C41—C51—C61 | 131.2 (2) | F22A—C62—C52 | 113.6 (6) |
F11—C61—F21 | 106.1 (2) | F32A—C62—C52 | 112.8 (7) |
F11—C61—F31 | 106.2 (2) | F32A—C62—F12A | 105.7 (7) |
F11—C61—C51 | 112.8 (3) | F32A—C62—F22A | 105.5 (7) |
F21—C61—F31 | 106.2 (3) | F12B—C62—C52 | 112.8 (11) |
F21—C61—C51 | 112.2 (2) | F12B—C62—F22B | 104.6 (13) |
F31—C61—C51 | 112.8 (2) | F12B—C62—F32B | 110.7 (12) |
C81—C71—C41 | 119.4 (3) | F22B—C62—C52 | 112.7 (13) |
C121—C71—C41 | 121.7 (2) | F32B—C62—C52 | 108.0 (8) |
C121—C71—C81 | 118.9 (2) | F32B—C62—F22B | 108.0 (12) |
C71—C81—H81 | 120.1 | C82—C72—C42 | 119.0 (2) |
C91—C81—C71 | 119.8 (3) | C122—C72—C42 | 122.1 (2) |
C91—C81—H81 | 120.1 | C122—C72—C82 | 118.8 (2) |
C81—C91—H91 | 119.7 | C72—C82—H82 | 120.0 |
C101—C91—C81 | 120.6 (3) | C92—C82—C72 | 120.0 (3) |
C101—C91—H91 | 119.7 | C92—C82—H82 | 120.0 |
C91—C101—H101 | 120.0 | C82—C92—H92 | 119.8 |
C91—C101—C111 | 119.9 (3) | C82—C92—C102 | 120.4 (3) |
C111—C101—H101 | 120.0 | C102—C92—H92 | 119.8 |
C101—C111—H111 | 120.0 | C92—C102—H102 | 120.1 |
C101—C111—C121 | 119.9 (3) | C112—C102—C92 | 119.9 (3) |
C121—C111—H111 | 120.0 | C112—C102—H102 | 120.1 |
C71—C121—H121 | 119.6 | C102—C112—H112 | 119.7 |
C111—C121—C71 | 120.8 (3) | C102—C112—C122 | 120.6 (3) |
C111—C121—H121 | 119.6 | C122—C112—H112 | 119.7 |
C141—C131—N11 | 119.3 (2) | C72—C122—H122 | 119.8 |
C181—C131—N11 | 119.9 (2) | C112—C122—C72 | 120.4 (3) |
C181—C131—C141 | 120.8 (2) | C112—C122—H122 | 119.8 |
C131—C141—H141 | 119.5 | C142—C132—N12 | 119.7 (2) |
C131—C141—C151 | 120.9 (3) | C182—C132—N12 | 119.1 (2) |
C151—C141—H141 | 119.5 | C182—C132—C142 | 121.1 (2) |
C141—C151—C161 | 118.9 (3) | C132—C142—H142 | 119.5 |
C141—C151—C191 | 119.2 (3) | C152—C142—C132 | 121.1 (2) |
C161—C151—C191 | 121.9 (2) | C152—C142—H142 | 119.5 |
C151—C161—C201 | 121.3 (3) | C142—C152—C162 | 118.7 (2) |
C171—C161—C151 | 118.8 (2) | C142—C152—C192 | 120.2 (2) |
C171—C161—C201 | 119.9 (3) | C162—C152—C192 | 121.2 (2) |
C161—C171—H171 | 118.9 | C152—C162—C202 | 120.5 (2) |
C181—C171—C161 | 122.2 (3) | C172—C162—C152 | 118.7 (2) |
C181—C171—H171 | 118.9 | C172—C162—C202 | 120.8 (2) |
C131—C181—C171 | 118.3 (3) | C162—C172—H172 | 118.6 |
C131—C181—H181 | 120.9 | C182—C172—C162 | 122.8 (3) |
C171—C181—H181 | 120.9 | C182—C172—H172 | 118.6 |
C151—C191—H19D | 109.5 | C132—C182—C172 | 117.7 (2) |
C151—C191—H19E | 109.5 | C132—C182—H182 | 121.2 |
C151—C191—H19F | 109.5 | C172—C182—H182 | 121.2 |
H19D—C191—H19E | 109.5 | C152—C192—H19A | 109.5 |
H19D—C191—H19F | 109.5 | C152—C192—H19B | 109.5 |
H19E—C191—H19F | 109.5 | C152—C192—H19C | 109.5 |
C161—C201—H20D | 109.5 | H19A—C192—H19B | 109.5 |
C161—C201—H20E | 109.5 | H19A—C192—H19C | 109.5 |
C161—C201—H20F | 109.5 | H19B—C192—H19C | 109.5 |
H20D—C201—H20E | 109.5 | C162—C202—H20A | 109.5 |
H20D—C201—H20F | 109.5 | C162—C202—H20B | 109.5 |
H20E—C201—H20F | 109.5 | C162—C202—H20C | 109.5 |
N22—N12—C52 | 110.0 (2) | H20A—C202—H20B | 109.5 |
N22—N12—C132 | 119.5 (2) | H20A—C202—H20C | 109.5 |
C52—N12—C132 | 130.5 (2) | H20B—C202—H20C | 109.5 |
1-(3,4-Dimethylphenyl)-4-(3-methoxyphenyl)-5-trifluoromethyl-1
H-1,2,3-triazole (2_C18H16F3N3O_3OMe34)
top
Crystal data top
C18H16F3N3O | Dx = 1.353 Mg m−3 |
Mr = 347.34 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 6163 reflections |
a = 9.5097 (13) Å | θ = 2.5–23.0° |
b = 17.921 (2) Å | µ = 0.11 mm−1 |
c = 20.011 (3) Å | T = 296 K |
V = 3410.3 (8) Å3 | Prism, colourless |
Z = 8 | 0.78 × 0.37 × 0.32 mm |
F(000) = 1440 | |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.070 |
phi and ω scans | θmax = 25.0°, θmin = 2.0° |
24398 measured reflections | h = −11→11 |
3001 independent reflections | k = −21→18 |
1986 reflections with I > 2σ(I) | l = −23→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.6011P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3001 reflections | Δρmax = 0.13 e Å−3 |
226 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C4 | 0.45657 (19) | 0.13444 (10) | 0.53652 (8) | 0.0517 (5) | |
C5 | 0.51589 (19) | 0.11231 (10) | 0.47700 (8) | 0.0513 (5) | |
C6 | 0.4518 (2) | 0.08305 (12) | 0.41461 (10) | 0.0624 (5) | |
C7 | 0.30890 (18) | 0.14475 (10) | 0.55692 (9) | 0.0515 (5) | |
C8 | 0.27036 (18) | 0.12856 (10) | 0.62260 (9) | 0.0539 (5) | |
H8 | 0.336611 | 0.109980 | 0.652467 | 0.065* | |
C9 | 0.1333 (2) | 0.14023 (11) | 0.64313 (10) | 0.0616 (5) | |
C10 | 0.0346 (2) | 0.16762 (11) | 0.59890 (12) | 0.0689 (6) | |
H10 | −0.057596 | 0.175192 | 0.612864 | 0.083* | |
C11 | 0.0726 (2) | 0.18369 (12) | 0.53428 (12) | 0.0681 (6) | |
H11 | 0.005582 | 0.202003 | 0.504652 | 0.082* | |
C12 | 0.2090 (2) | 0.17299 (11) | 0.51278 (10) | 0.0623 (5) | |
H12 | 0.234105 | 0.184570 | 0.469075 | 0.075* | |
C13 | 0.77078 (19) | 0.10712 (11) | 0.43884 (9) | 0.0547 (5) | |
C14 | 0.7871 (2) | 0.15926 (11) | 0.38891 (9) | 0.0594 (5) | |
H14 | 0.725376 | 0.199398 | 0.386202 | 0.071* | |
C15 | 0.8952 (2) | 0.15240 (12) | 0.34245 (9) | 0.0627 (5) | |
C16 | 0.9859 (2) | 0.09124 (13) | 0.34746 (10) | 0.0636 (5) | |
C17 | 0.9668 (2) | 0.04048 (12) | 0.39842 (11) | 0.0694 (6) | |
H17 | 1.028383 | 0.000337 | 0.401877 | 0.083* | |
C18 | 0.8598 (2) | 0.04716 (11) | 0.44441 (11) | 0.0646 (5) | |
H18 | 0.848183 | 0.012082 | 0.478216 | 0.078* | |
C19 | 0.9127 (3) | 0.21093 (14) | 0.28922 (11) | 0.0925 (8) | |
H19A | 0.829265 | 0.240984 | 0.286963 | 0.139* | |
H19B | 0.928131 | 0.187197 | 0.246845 | 0.139* | |
H19C | 0.991846 | 0.241980 | 0.299887 | 0.139* | |
C20 | 1.1031 (2) | 0.07970 (17) | 0.29777 (13) | 0.0988 (8) | |
H20A | 1.160591 | 0.038568 | 0.311813 | 0.148* | |
H20B | 1.159390 | 0.124064 | 0.295249 | 0.148* | |
H20C | 1.063802 | 0.069116 | 0.254602 | 0.148* | |
C21 | 0.1781 (3) | 0.09107 (18) | 0.75216 (12) | 0.1067 (9) | |
H21A | 0.205598 | 0.043296 | 0.734837 | 0.160* | |
H21B | 0.131728 | 0.084499 | 0.794364 | 0.160* | |
H21C | 0.260040 | 0.121655 | 0.758145 | 0.160* | |
F1 | 0.33196 (13) | 0.04803 (7) | 0.42676 (6) | 0.0849 (4) | |
F2 | 0.42400 (15) | 0.13635 (8) | 0.37093 (6) | 0.0985 (5) | |
F3 | 0.53445 (14) | 0.03468 (8) | 0.38283 (6) | 0.0935 (4) | |
N1 | 0.65692 (16) | 0.11688 (9) | 0.48613 (7) | 0.0562 (4) | |
N2 | 0.68475 (17) | 0.13996 (10) | 0.54906 (8) | 0.0681 (5) | |
N3 | 0.56389 (16) | 0.14978 (10) | 0.57937 (8) | 0.0642 (5) | |
O1 | 0.08504 (15) | 0.12619 (10) | 0.70658 (8) | 0.0888 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C4 | 0.0570 (10) | 0.0560 (12) | 0.0421 (10) | −0.0035 (8) | −0.0041 (9) | 0.0061 (8) |
C5 | 0.0544 (11) | 0.0558 (11) | 0.0436 (10) | −0.0080 (8) | −0.0023 (8) | 0.0065 (8) |
C6 | 0.0669 (13) | 0.0722 (14) | 0.0480 (11) | −0.0098 (11) | 0.0004 (10) | 0.0004 (10) |
C7 | 0.0547 (10) | 0.0512 (11) | 0.0487 (10) | −0.0029 (9) | −0.0038 (8) | −0.0003 (8) |
C8 | 0.0525 (11) | 0.0588 (12) | 0.0504 (11) | 0.0035 (9) | −0.0018 (8) | 0.0020 (9) |
C9 | 0.0608 (12) | 0.0607 (13) | 0.0633 (12) | 0.0039 (10) | 0.0056 (10) | −0.0009 (10) |
C10 | 0.0523 (11) | 0.0661 (14) | 0.0885 (16) | 0.0042 (10) | −0.0008 (11) | −0.0039 (12) |
C11 | 0.0631 (13) | 0.0621 (13) | 0.0792 (16) | 0.0038 (10) | −0.0217 (11) | −0.0005 (11) |
C12 | 0.0708 (13) | 0.0622 (13) | 0.0539 (11) | −0.0003 (10) | −0.0116 (10) | 0.0025 (10) |
C13 | 0.0544 (11) | 0.0603 (12) | 0.0495 (11) | −0.0084 (9) | 0.0020 (8) | −0.0011 (9) |
C14 | 0.0705 (12) | 0.0559 (12) | 0.0519 (11) | 0.0019 (9) | 0.0072 (9) | −0.0029 (9) |
C15 | 0.0761 (13) | 0.0641 (13) | 0.0479 (11) | −0.0129 (11) | 0.0075 (10) | −0.0089 (10) |
C16 | 0.0538 (11) | 0.0788 (15) | 0.0580 (12) | −0.0047 (11) | 0.0017 (9) | −0.0170 (11) |
C17 | 0.0598 (12) | 0.0726 (14) | 0.0758 (14) | 0.0081 (10) | −0.0046 (11) | −0.0095 (12) |
C18 | 0.0648 (12) | 0.0610 (13) | 0.0680 (13) | −0.0042 (10) | −0.0021 (10) | 0.0060 (10) |
C19 | 0.130 (2) | 0.0872 (17) | 0.0604 (14) | −0.0072 (15) | 0.0313 (14) | 0.0029 (13) |
C20 | 0.0790 (15) | 0.143 (2) | 0.0744 (16) | 0.0114 (16) | 0.0131 (13) | −0.0189 (16) |
C21 | 0.0996 (19) | 0.154 (3) | 0.0662 (15) | 0.0239 (18) | 0.0215 (14) | 0.0312 (17) |
F1 | 0.0766 (8) | 0.1095 (10) | 0.0685 (8) | −0.0362 (7) | −0.0014 (6) | −0.0132 (7) |
F2 | 0.1292 (12) | 0.1098 (11) | 0.0566 (7) | −0.0205 (9) | −0.0288 (7) | 0.0222 (7) |
F3 | 0.0889 (9) | 0.1118 (11) | 0.0798 (9) | −0.0044 (8) | 0.0009 (7) | −0.0407 (8) |
N1 | 0.0566 (9) | 0.0673 (11) | 0.0447 (9) | −0.0071 (7) | 0.0004 (7) | 0.0026 (7) |
N2 | 0.0585 (10) | 0.0978 (14) | 0.0480 (9) | −0.0076 (9) | −0.0043 (8) | −0.0046 (9) |
N3 | 0.0567 (10) | 0.0892 (13) | 0.0467 (9) | −0.0045 (8) | −0.0032 (8) | −0.0030 (8) |
O1 | 0.0748 (10) | 0.1169 (13) | 0.0747 (10) | 0.0205 (9) | 0.0239 (8) | 0.0132 (10) |
Geometric parameters (Å, º) top
C4—C5 | 1.376 (2) | C11—C12 | 1.381 (3) |
C4—C7 | 1.474 (2) | C13—C14 | 1.377 (3) |
C4—N3 | 1.361 (2) | C13—C18 | 1.373 (3) |
C5—C6 | 1.485 (3) | C13—N1 | 1.449 (2) |
C5—N1 | 1.356 (2) | C14—C15 | 1.392 (3) |
C6—F1 | 1.324 (2) | C15—C16 | 1.398 (3) |
C6—F2 | 1.321 (2) | C15—C19 | 1.504 (3) |
C6—F3 | 1.332 (2) | C16—C17 | 1.378 (3) |
C7—C8 | 1.395 (2) | C16—C20 | 1.507 (3) |
C7—C12 | 1.392 (2) | C17—C18 | 1.377 (3) |
C8—C9 | 1.383 (3) | C21—O1 | 1.418 (3) |
C9—C10 | 1.380 (3) | N1—N2 | 1.352 (2) |
C9—O1 | 1.373 (2) | N2—N3 | 1.311 (2) |
C10—C11 | 1.373 (3) | | |
| | | |
C5—C4—C7 | 131.78 (16) | C10—C11—C12 | 120.76 (19) |
N3—C4—C5 | 107.22 (15) | C11—C12—C7 | 119.61 (19) |
N3—C4—C7 | 120.98 (16) | C14—C13—N1 | 118.45 (17) |
C4—C5—C6 | 131.40 (17) | C18—C13—C14 | 121.38 (18) |
N1—C5—C4 | 105.74 (15) | C18—C13—N1 | 120.17 (17) |
N1—C5—C6 | 122.71 (16) | C13—C14—C15 | 120.54 (19) |
F1—C6—C5 | 111.49 (16) | C14—C15—C16 | 118.50 (18) |
F1—C6—F3 | 106.69 (17) | C14—C15—C19 | 119.5 (2) |
F2—C6—C5 | 112.53 (18) | C16—C15—C19 | 121.96 (19) |
F2—C6—F1 | 106.95 (17) | C15—C16—C20 | 121.1 (2) |
F2—C6—F3 | 105.84 (16) | C17—C16—C15 | 119.28 (18) |
F3—C6—C5 | 112.92 (17) | C17—C16—C20 | 119.7 (2) |
C8—C7—C4 | 119.02 (16) | C18—C17—C16 | 122.3 (2) |
C12—C7—C4 | 121.32 (17) | C13—C18—C17 | 118.00 (19) |
C12—C7—C8 | 119.61 (17) | C5—N1—C13 | 130.09 (15) |
C9—C8—C7 | 119.75 (17) | N2—N1—C5 | 109.74 (15) |
C10—C9—C8 | 120.29 (19) | N2—N1—C13 | 119.94 (14) |
O1—C9—C8 | 124.19 (18) | N3—N2—N1 | 107.47 (14) |
O1—C9—C10 | 115.53 (18) | N2—N3—C4 | 109.81 (15) |
C11—C10—C9 | 119.98 (19) | C9—O1—C21 | 117.87 (16) |
| | | |
C4—C5—C6—F1 | −27.8 (3) | C13—C14—C15—C19 | −178.75 (19) |
C4—C5—C6—F2 | 92.4 (2) | C13—N1—N2—N3 | 175.11 (16) |
C4—C5—C6—F3 | −147.9 (2) | C14—C13—C18—C17 | 0.1 (3) |
C4—C5—N1—C13 | −173.58 (18) | C14—C13—N1—C5 | 68.0 (3) |
C4—C5—N1—N2 | 0.8 (2) | C14—C13—N1—N2 | −105.9 (2) |
C4—C7—C8—C9 | 177.89 (17) | C14—C15—C16—C17 | −0.9 (3) |
C4—C7—C12—C11 | −178.29 (18) | C14—C15—C16—C20 | 178.61 (19) |
C5—C4—C7—C8 | 145.9 (2) | C15—C16—C17—C18 | 1.0 (3) |
C5—C4—C7—C12 | −36.7 (3) | C16—C17—C18—C13 | −0.6 (3) |
C5—C4—N3—N2 | 1.4 (2) | C18—C13—C14—C15 | 0.0 (3) |
C5—N1—N2—N3 | 0.1 (2) | C18—C13—N1—C5 | −112.2 (2) |
C6—C5—N1—C13 | 10.4 (3) | C18—C13—N1—N2 | 73.9 (2) |
C6—C5—N1—N2 | −175.27 (17) | C19—C15—C16—C17 | 178.3 (2) |
C7—C4—C5—C6 | −7.7 (4) | C19—C15—C16—C20 | −2.3 (3) |
C7—C4—C5—N1 | 176.71 (18) | C20—C16—C17—C18 | −178.5 (2) |
C7—C4—N3—N2 | −176.86 (16) | N1—C5—C6—F1 | 147.14 (18) |
C7—C8—C9—C10 | 0.2 (3) | N1—C5—C6—F2 | −92.7 (2) |
C7—C8—C9—O1 | −179.90 (19) | N1—C5—C6—F3 | 27.0 (3) |
C8—C7—C12—C11 | −0.9 (3) | N1—C13—C14—C15 | 179.78 (16) |
C8—C9—C10—C11 | −0.3 (3) | N1—C13—C18—C17 | −179.72 (17) |
C8—C9—O1—C21 | −6.1 (3) | N1—N2—N3—C4 | −0.9 (2) |
C9—C10—C11—C12 | −0.2 (3) | N3—C4—C5—C6 | 174.3 (2) |
C10—C9—O1—C21 | 173.8 (2) | N3—C4—C5—N1 | −1.3 (2) |
C10—C11—C12—C7 | 0.8 (3) | N3—C4—C7—C8 | −36.3 (3) |
C12—C7—C8—C9 | 0.4 (3) | N3—C4—C7—C12 | 141.13 (19) |
C13—C14—C15—C16 | 0.4 (3) | O1—C9—C10—C11 | 179.77 (19) |
1-(3,4-Dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1
H-1,2,3-triazole (3_C18H16F3N3O_4OMe34)
top
Crystal data top
C18H16F3N3O | F(000) = 720 |
Mr = 347.34 | Dx = 1.383 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1368 (16) Å | Cell parameters from 2495 reflections |
b = 7.7224 (9) Å | θ = 2.4–22.3° |
c = 15.4446 (18) Å | µ = 0.11 mm−1 |
β = 112.454 (2)° | T = 296 K |
V = 1668.5 (3) Å3 | Prism, colourless |
Z = 4 | 0.36 × 0.23 × 0.2 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.045 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
phi and ω scans | h = −13→18 |
12266 measured reflections | k = −6→9 |
2930 independent reflections | l = −18→18 |
1644 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.053P)2 + 0.0053P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2930 reflections | Δρmax = 0.15 e Å−3 |
254 parameters | Δρmin = −0.13 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C4 | 0.93725 (15) | 0.4081 (3) | 0.12782 (13) | 0.0499 (5) | |
C5 | 0.86075 (15) | 0.2987 (3) | 0.09070 (13) | 0.0508 (5) | |
N1 | 0.78596 (12) | 0.3801 (2) | 0.10140 (11) | 0.0547 (5) | |
C7 | 1.03822 (14) | 0.3954 (2) | 0.14026 (13) | 0.0494 (5) | |
C12 | 1.06877 (16) | 0.3365 (3) | 0.07057 (13) | 0.0568 (6) | |
H12 | 1.023688 | 0.300023 | 0.013383 | 0.068* | |
C11 | 1.16373 (16) | 0.3317 (3) | 0.08504 (14) | 0.0602 (6) | |
H11 | 1.182349 | 0.291691 | 0.037771 | 0.072* | |
C10 | 1.23252 (16) | 0.3859 (3) | 0.16955 (14) | 0.0561 (6) | |
C9 | 1.20406 (16) | 0.4474 (3) | 0.23901 (14) | 0.0597 (6) | |
H9 | 1.249274 | 0.485992 | 0.295640 | 0.072* | |
C8 | 1.10823 (16) | 0.4510 (3) | 0.22363 (13) | 0.0577 (6) | |
H8 | 1.089851 | 0.492092 | 0.270839 | 0.069* | |
C13 | 0.68774 (15) | 0.3272 (3) | 0.07683 (15) | 0.0543 (5) | |
C14 | 0.62510 (15) | 0.3317 (2) | −0.01507 (14) | 0.0560 (6) | |
H14 | 0.646474 | 0.367211 | −0.061250 | 0.067* | |
C15 | 0.52962 (16) | 0.2833 (2) | −0.03990 (14) | 0.0547 (6) | |
C16 | 0.49917 (16) | 0.2331 (3) | 0.03122 (16) | 0.0575 (6) | |
C17 | 0.56329 (18) | 0.2312 (3) | 0.12258 (16) | 0.0694 (7) | |
H17 | 0.542310 | 0.198475 | 0.169471 | 0.083* | |
C18 | 0.65795 (18) | 0.2765 (3) | 0.14683 (15) | 0.0656 (6) | |
H18 | 0.700601 | 0.272849 | 0.208944 | 0.079* | |
C21 | 1.39830 (16) | 0.4186 (3) | 0.26503 (18) | 0.0847 (8) | |
H21A | 1.390735 | 0.537335 | 0.279363 | 0.127* | |
H21B | 1.459662 | 0.403551 | 0.261226 | 0.127* | |
H21C | 1.393847 | 0.345369 | 0.313420 | 0.127* | |
C19 | 0.46274 (16) | 0.2853 (3) | −0.14122 (15) | 0.0798 (7) | |
H19A | 0.496027 | 0.327359 | −0.178884 | 0.120* | |
H19B | 0.409508 | 0.359779 | −0.148830 | 0.120* | |
H19C | 0.440024 | 0.170028 | −0.160587 | 0.120* | |
C20 | 0.39630 (16) | 0.1806 (3) | 0.00797 (18) | 0.0801 (7) | |
H20A | 0.386211 | 0.161333 | 0.064915 | 0.120* | |
H20B | 0.382839 | 0.076031 | −0.028404 | 0.120* | |
H20C | 0.354595 | 0.271102 | −0.027359 | 0.120* | |
C6 | 0.8518 (2) | 0.1193 (4) | 0.0541 (2) | 0.0735 (8) | |
N2 | 0.81480 (14) | 0.5342 (2) | 0.14348 (12) | 0.0667 (5) | |
N3 | 0.90597 (14) | 0.5511 (2) | 0.15941 (12) | 0.0632 (5) | |
O1 | 1.32510 (11) | 0.3737 (2) | 0.17768 (11) | 0.0741 (5) | |
F1 | 0.9321 (10) | 0.0565 (19) | 0.0516 (13) | 0.091 (3) | 0.52 (2) |
F2 | 0.7859 (4) | 0.0920 (10) | −0.0236 (6) | 0.084 (3) | 0.52 (2) |
F3 | 0.8295 (8) | 0.0123 (10) | 0.1138 (6) | 0.107 (3) | 0.52 (2) |
F1' | 0.9333 (11) | 0.051 (2) | 0.0709 (16) | 0.108 (5) | 0.48 (2) |
F2' | 0.8105 (15) | 0.136 (2) | −0.0456 (10) | 0.186 (6) | 0.48 (2) |
F3' | 0.8016 (14) | 0.0178 (14) | 0.076 (2) | 0.180 (6) | 0.48 (2) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C4 | 0.0551 (14) | 0.0482 (13) | 0.0428 (11) | 0.0035 (11) | 0.0147 (10) | −0.0022 (9) |
C5 | 0.0499 (14) | 0.0481 (13) | 0.0497 (12) | 0.0044 (11) | 0.0138 (10) | −0.0031 (9) |
N1 | 0.0529 (12) | 0.0529 (11) | 0.0537 (10) | 0.0015 (9) | 0.0152 (8) | −0.0078 (8) |
C7 | 0.0580 (14) | 0.0417 (12) | 0.0459 (11) | 0.0012 (10) | 0.0171 (10) | 0.0003 (9) |
C12 | 0.0656 (16) | 0.0557 (14) | 0.0441 (11) | 0.0009 (11) | 0.0154 (11) | −0.0050 (10) |
C11 | 0.0717 (17) | 0.0607 (15) | 0.0517 (13) | 0.0023 (12) | 0.0274 (12) | −0.0029 (10) |
C10 | 0.0582 (15) | 0.0506 (14) | 0.0611 (14) | −0.0001 (11) | 0.0247 (12) | 0.0006 (10) |
C9 | 0.0577 (16) | 0.0634 (15) | 0.0523 (13) | −0.0043 (11) | 0.0146 (11) | −0.0097 (10) |
C8 | 0.0623 (16) | 0.0615 (15) | 0.0493 (12) | −0.0013 (11) | 0.0213 (11) | −0.0115 (10) |
C13 | 0.0528 (15) | 0.0491 (13) | 0.0589 (13) | 0.0075 (10) | 0.0190 (11) | −0.0002 (10) |
C14 | 0.0632 (16) | 0.0515 (13) | 0.0548 (13) | 0.0040 (11) | 0.0241 (11) | 0.0014 (10) |
C15 | 0.0546 (15) | 0.0443 (12) | 0.0620 (13) | 0.0071 (10) | 0.0188 (11) | 0.0009 (10) |
C16 | 0.0595 (16) | 0.0456 (13) | 0.0743 (16) | 0.0093 (11) | 0.0333 (13) | 0.0010 (11) |
C17 | 0.0794 (19) | 0.0693 (16) | 0.0721 (16) | 0.0071 (13) | 0.0430 (15) | 0.0075 (12) |
C18 | 0.0694 (17) | 0.0720 (16) | 0.0562 (13) | 0.0084 (13) | 0.0248 (12) | 0.0050 (11) |
C21 | 0.0561 (16) | 0.092 (2) | 0.100 (2) | −0.0124 (13) | 0.0228 (14) | −0.0208 (15) |
C19 | 0.0715 (17) | 0.0875 (19) | 0.0698 (16) | 0.0022 (13) | 0.0151 (13) | 0.0000 (13) |
C20 | 0.0707 (18) | 0.0686 (17) | 0.113 (2) | 0.0049 (13) | 0.0481 (15) | 0.0022 (14) |
C6 | 0.0541 (19) | 0.0656 (19) | 0.090 (2) | 0.0054 (16) | 0.0160 (19) | −0.0199 (16) |
N2 | 0.0631 (14) | 0.0611 (13) | 0.0744 (13) | 0.0006 (10) | 0.0244 (10) | −0.0171 (10) |
N3 | 0.0620 (14) | 0.0568 (12) | 0.0696 (12) | −0.0001 (10) | 0.0238 (10) | −0.0150 (9) |
O1 | 0.0613 (11) | 0.0850 (12) | 0.0791 (11) | −0.0036 (9) | 0.0302 (9) | −0.0090 (9) |
F1 | 0.065 (6) | 0.070 (6) | 0.147 (7) | −0.012 (5) | 0.051 (5) | −0.053 (5) |
F2 | 0.070 (5) | 0.077 (4) | 0.077 (4) | 0.012 (2) | −0.006 (3) | −0.038 (3) |
F3 | 0.157 (7) | 0.047 (3) | 0.129 (5) | −0.019 (3) | 0.070 (4) | 0.011 (3) |
F1' | 0.079 (7) | 0.061 (5) | 0.157 (9) | 0.022 (5) | 0.014 (5) | −0.013 (5) |
F2' | 0.263 (10) | 0.160 (8) | 0.087 (5) | 0.036 (7) | 0.014 (6) | −0.063 (5) |
F3' | 0.123 (8) | 0.088 (6) | 0.377 (19) | −0.045 (5) | 0.149 (12) | −0.090 (9) |
Geometric parameters (Å, º) top
C4—C5 | 1.369 (3) | C13—C18 | 1.378 (3) |
C4—C7 | 1.469 (3) | C14—C15 | 1.397 (3) |
C4—N3 | 1.363 (2) | C15—C16 | 1.399 (3) |
C5—N1 | 1.359 (2) | C15—C19 | 1.505 (3) |
C5—C6 | 1.483 (3) | C16—C17 | 1.374 (3) |
N1—C13 | 1.446 (2) | C16—C20 | 1.514 (3) |
N1—N2 | 1.346 (2) | C17—C18 | 1.381 (3) |
C7—C12 | 1.400 (3) | C21—O1 | 1.424 (2) |
C7—C8 | 1.387 (3) | C6—F1 | 1.323 (14) |
C12—C11 | 1.368 (3) | C6—F2 | 1.250 (7) |
C11—C10 | 1.387 (3) | C6—F3 | 1.373 (8) |
C10—C9 | 1.384 (3) | C6—F1' | 1.274 (15) |
C10—O1 | 1.362 (2) | C6—F2' | 1.429 (14) |
C9—C8 | 1.378 (3) | C6—F3' | 1.224 (12) |
C13—C14 | 1.374 (3) | N2—N3 | 1.313 (2) |
| | | |
C5—C4—C7 | 133.23 (19) | C14—C15—C16 | 118.38 (19) |
N3—C4—C5 | 107.20 (19) | C14—C15—C19 | 119.8 (2) |
N3—C4—C7 | 119.55 (18) | C16—C15—C19 | 121.8 (2) |
C4—C5—C6 | 132.5 (2) | C15—C16—C20 | 120.4 (2) |
N1—C5—C4 | 105.93 (18) | C17—C16—C15 | 119.6 (2) |
N1—C5—C6 | 121.3 (2) | C17—C16—C20 | 120.0 (2) |
C5—N1—C13 | 131.18 (17) | C16—C17—C18 | 121.9 (2) |
N2—N1—C5 | 109.63 (17) | C13—C18—C17 | 118.4 (2) |
N2—N1—C13 | 119.19 (17) | F1—C6—C5 | 113.7 (6) |
C12—C7—C4 | 123.63 (18) | F1—C6—F3 | 105.3 (9) |
C8—C7—C4 | 119.27 (18) | F2—C6—C5 | 116.5 (4) |
C8—C7—C12 | 117.0 (2) | F2—C6—F1 | 108.3 (8) |
C11—C12—C7 | 121.22 (19) | F2—C6—F3 | 103.5 (6) |
C12—C11—C10 | 120.6 (2) | F3—C6—C5 | 108.4 (5) |
C9—C10—C11 | 119.3 (2) | F1'—C6—C5 | 111.5 (8) |
O1—C10—C11 | 116.22 (19) | F1'—C6—F2' | 104.3 (10) |
O1—C10—C9 | 124.50 (19) | F2'—C6—C5 | 105.5 (7) |
C8—C9—C10 | 119.48 (19) | F3'—C6—C5 | 118.0 (7) |
C9—C8—C7 | 122.34 (19) | F3'—C6—F1' | 109.6 (11) |
C14—C13—N1 | 119.93 (19) | F3'—C6—F2' | 106.8 (8) |
C14—C13—C18 | 121.0 (2) | N3—N2—N1 | 107.59 (16) |
C18—C13—N1 | 119.10 (19) | N2—N3—C4 | 109.66 (17) |
C13—C14—C15 | 120.7 (2) | C10—O1—C21 | 118.13 (17) |
| | | |
C4—C5—N1—C13 | −179.11 (19) | C12—C7—C8—C9 | −0.8 (3) |
C4—C5—N1—N2 | 0.1 (2) | C12—C11—C10—C9 | −0.9 (3) |
C4—C5—C6—F1 | −4.8 (10) | C12—C11—C10—O1 | 179.03 (17) |
C4—C5—C6—F2 | −131.9 (6) | C11—C10—C9—C8 | 1.1 (3) |
C4—C5—C6—F3 | 111.9 (6) | C11—C10—O1—C21 | −176.53 (19) |
C4—C5—C6—F1' | 9.0 (12) | C10—C9—C8—C7 | −0.3 (3) |
C4—C5—C6—F2' | −103.7 (12) | C9—C10—O1—C21 | 3.3 (3) |
C4—C5—C6—F3' | 137.1 (15) | C8—C7—C12—C11 | 1.0 (3) |
C4—C7—C12—C11 | 178.24 (18) | C13—N1—N2—N3 | 179.25 (16) |
C4—C7—C8—C9 | −178.14 (18) | C13—C14—C15—C16 | 1.0 (3) |
C5—C4—C7—C12 | 45.3 (3) | C13—C14—C15—C19 | −178.63 (19) |
C5—C4—C7—C8 | −137.5 (2) | C14—C13—C18—C17 | −0.4 (3) |
C5—C4—N3—N2 | 0.0 (2) | C14—C15—C16—C17 | −0.5 (3) |
C5—N1—C13—C14 | −75.4 (3) | C14—C15—C16—C20 | 179.64 (18) |
C5—N1—C13—C18 | 106.0 (2) | C15—C16—C17—C18 | −0.5 (3) |
C5—N1—N2—N3 | 0.0 (2) | C16—C17—C18—C13 | 1.0 (3) |
N1—C5—C6—F1 | −177.4 (9) | C18—C13—C14—C15 | −0.5 (3) |
N1—C5—C6—F2 | 55.5 (7) | C19—C15—C16—C17 | 179.12 (19) |
N1—C5—C6—F3 | −60.7 (6) | C19—C15—C16—C20 | −0.7 (3) |
N1—C5—C6—F1' | −163.6 (11) | C20—C16—C17—C18 | 179.37 (19) |
N1—C5—C6—F2' | 83.7 (12) | C6—C5—N1—C13 | −4.8 (3) |
N1—C5—C6—F3' | −35.5 (16) | C6—C5—N1—N2 | 174.4 (2) |
N1—C13—C14—C15 | −179.10 (17) | N2—N1—C13—C14 | 105.5 (2) |
N1—C13—C18—C17 | 178.13 (18) | N2—N1—C13—C18 | −73.1 (2) |
N1—N2—N3—C4 | 0.0 (2) | N3—C4—C5—N1 | −0.1 (2) |
C7—C4—C5—N1 | 178.12 (19) | N3—C4—C5—C6 | −173.5 (2) |
C7—C4—C5—C6 | 4.7 (4) | N3—C4—C7—C12 | −136.7 (2) |
C7—C4—N3—N2 | −178.43 (16) | N3—C4—C7—C8 | 40.5 (3) |
C7—C12—C11—C10 | −0.2 (3) | O1—C10—C9—C8 | −178.80 (18) |
1-(2,4-Dimethylphenyl)-4-(4-methoxyphenyl)-5-trifluoromethyl-1
H-1,2,3-triazole (4_4OMe24Me)
top
Crystal data top
C18H16F3N3O | Z = 2 |
Mr = 347.34 | F(000) = 360 |
Triclinic, P1 | Dx = 1.343 Mg m−3 |
a = 8.829 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.513 (2) Å | Cell parameters from 1698 reflections |
c = 11.598 (3) Å | θ = 2.4–23.5° |
α = 106.105 (4)° | µ = 0.11 mm−1 |
β = 95.554 (4)° | T = 293 K |
γ = 110.049 (4)° | Prismatic, colorless |
V = 859.1 (4) Å3 | 0.72 × 0.23 × 0.13 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.092 |
phi and ω scans | θmax = 25.5°, θmin = 1.9° |
6496 measured reflections | h = −10→10 |
3096 independent reflections | k = −11→11 |
1709 reflections with I > 2σ(I) | l = −14→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
3096 reflections | Δρmax = 0.23 e Å−3 |
254 parameters | Δρmin = −0.14 e Å−3 |
292 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C21 | −0.2723 (3) | 0.4401 (5) | 0.1277 (3) | 0.1030 (12) | |
H21A | −0.349309 | 0.396692 | 0.050371 | 0.155* | |
H21B | −0.308799 | 0.373940 | 0.176948 | 0.155* | |
H21C | −0.265738 | 0.545027 | 0.169772 | 0.155* | |
F1A | 0.5992 (16) | 0.863 (2) | 0.3572 (15) | 0.121 (5) | 0.48 (3) |
F2A | 0.8012 (19) | 0.816 (2) | 0.416 (2) | 0.110 (4) | 0.48 (3) |
F3A | 0.772 (2) | 1.0149 (11) | 0.5188 (11) | 0.127 (4) | 0.48 (3) |
C4 | 0.4271 (3) | 0.6786 (3) | 0.5017 (2) | 0.0469 (6) | |
N1 | 0.6568 (2) | 0.7876 (2) | 0.63995 (18) | 0.0516 (5) | |
N2 | 0.5401 (3) | 0.7010 (3) | 0.6858 (2) | 0.0646 (6) | |
C8 | 0.1354 (3) | 0.6176 (3) | 0.4205 (2) | 0.0523 (6) | |
H8 | 0.125932 | 0.655038 | 0.501384 | 0.063* | |
O1 | −0.1156 (2) | 0.4471 (3) | 0.10743 (17) | 0.0830 (6) | |
C5 | 0.5900 (3) | 0.7766 (3) | 0.5244 (2) | 0.0464 (6) | |
N3 | 0.4021 (3) | 0.6347 (3) | 0.6036 (2) | 0.0641 (6) | |
C7 | 0.2876 (3) | 0.6213 (3) | 0.3969 (2) | 0.0476 (6) | |
C18 | 0.9423 (3) | 0.8184 (3) | 0.6932 (2) | 0.0592 (7) | |
H18 | 0.918317 | 0.722985 | 0.630980 | 0.071* | |
C12 | 0.2975 (3) | 0.5641 (3) | 0.2750 (2) | 0.0583 (7) | |
H12 | 0.397518 | 0.563510 | 0.256550 | 0.070* | |
C10 | 0.0121 (3) | 0.5060 (3) | 0.2072 (2) | 0.0585 (7) | |
C9 | −0.0025 (3) | 0.5598 (3) | 0.3273 (2) | 0.0563 (7) | |
H9 | −0.103664 | 0.557199 | 0.345213 | 0.068* | |
C11 | 0.1630 (3) | 0.5088 (3) | 0.1820 (2) | 0.0647 (7) | |
H11 | 0.172788 | 0.472726 | 0.101015 | 0.078* | |
C13 | 0.8214 (3) | 0.8776 (3) | 0.7137 (2) | 0.0488 (6) | |
C14 | 0.8521 (3) | 1.0193 (3) | 0.8045 (3) | 0.0637 (7) | |
C17 | 1.0983 (3) | 0.9015 (4) | 0.7652 (3) | 0.0695 (8) | |
H17 | 1.179193 | 0.860479 | 0.752133 | 0.083* | |
C15 | 1.0117 (4) | 1.0987 (4) | 0.8744 (3) | 0.0792 (9) | |
H15 | 1.035990 | 1.193929 | 0.936856 | 0.095* | |
C6 | 0.6859 (3) | 0.8668 (3) | 0.4524 (3) | 0.0599 (7) | |
F2B | 0.8099 (12) | 0.9917 (15) | 0.5138 (9) | 0.108 (3) | 0.52 (3) |
F3B | 0.5899 (16) | 0.9137 (18) | 0.3889 (16) | 0.106 (4) | 0.52 (3) |
F1B | 0.734 (3) | 0.7772 (16) | 0.3677 (14) | 0.120 (4) | 0.52 (3) |
C16 | 1.1371 (3) | 1.0440 (4) | 0.8563 (3) | 0.0728 (8) | |
C20 | 1.3089 (4) | 1.1376 (5) | 0.9345 (4) | 0.1147 (13) | |
H20A | 1.311734 | 1.233108 | 0.992634 | 0.172* | |
H20B | 1.338856 | 1.075074 | 0.977604 | 0.172* | |
H20C | 1.385341 | 1.164288 | 0.883001 | 0.172* | |
C19 | 0.7210 (4) | 1.0866 (4) | 0.8254 (4) | 0.1035 (12) | |
H19A | 0.766548 | 1.185267 | 0.892332 | 0.155* | |
H19B | 0.682842 | 1.104232 | 0.752394 | 0.155* | |
H19C | 0.630178 | 1.012962 | 0.844895 | 0.155* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C21 | 0.0532 (18) | 0.166 (4) | 0.066 (2) | 0.015 (2) | 0.0017 (16) | 0.042 (2) |
F1A | 0.065 (5) | 0.179 (11) | 0.098 (6) | −0.017 (5) | −0.007 (4) | 0.104 (7) |
F2A | 0.109 (7) | 0.132 (9) | 0.147 (11) | 0.067 (7) | 0.089 (6) | 0.086 (7) |
F3A | 0.191 (11) | 0.042 (4) | 0.118 (6) | 0.006 (4) | 0.046 (6) | 0.027 (3) |
C4 | 0.0461 (14) | 0.0468 (14) | 0.0522 (14) | 0.0160 (11) | 0.0166 (12) | 0.0235 (12) |
N1 | 0.0462 (12) | 0.0570 (13) | 0.0559 (13) | 0.0158 (10) | 0.0119 (10) | 0.0304 (11) |
N2 | 0.0498 (13) | 0.0872 (16) | 0.0631 (14) | 0.0154 (12) | 0.0138 (12) | 0.0474 (13) |
C8 | 0.0529 (14) | 0.0575 (15) | 0.0430 (14) | 0.0188 (12) | 0.0110 (12) | 0.0145 (12) |
O1 | 0.0617 (12) | 0.1139 (16) | 0.0495 (11) | 0.0094 (11) | 0.0024 (10) | 0.0253 (11) |
C5 | 0.0492 (14) | 0.0481 (14) | 0.0468 (14) | 0.0183 (12) | 0.0134 (11) | 0.0226 (11) |
N3 | 0.0473 (12) | 0.0807 (15) | 0.0659 (15) | 0.0134 (11) | 0.0115 (11) | 0.0414 (13) |
C7 | 0.0464 (14) | 0.0444 (13) | 0.0518 (15) | 0.0128 (11) | 0.0122 (12) | 0.0208 (11) |
C18 | 0.0531 (15) | 0.0571 (16) | 0.0694 (18) | 0.0211 (13) | 0.0179 (14) | 0.0227 (14) |
C12 | 0.0529 (15) | 0.0635 (16) | 0.0584 (16) | 0.0182 (13) | 0.0214 (13) | 0.0222 (14) |
C10 | 0.0542 (15) | 0.0608 (16) | 0.0463 (15) | 0.0075 (12) | 0.0039 (13) | 0.0175 (13) |
C9 | 0.0478 (14) | 0.0652 (17) | 0.0544 (16) | 0.0189 (13) | 0.0126 (13) | 0.0206 (13) |
C11 | 0.0647 (17) | 0.0735 (18) | 0.0448 (15) | 0.0138 (14) | 0.0185 (14) | 0.0169 (14) |
C13 | 0.0442 (13) | 0.0483 (14) | 0.0550 (15) | 0.0124 (11) | 0.0090 (12) | 0.0262 (13) |
C14 | 0.0636 (17) | 0.0575 (16) | 0.0682 (18) | 0.0238 (14) | 0.0103 (14) | 0.0188 (14) |
C17 | 0.0517 (16) | 0.082 (2) | 0.083 (2) | 0.0263 (15) | 0.0159 (15) | 0.0386 (17) |
C15 | 0.080 (2) | 0.0717 (19) | 0.0649 (19) | 0.0157 (16) | 0.0099 (16) | 0.0102 (16) |
C6 | 0.0527 (17) | 0.0632 (19) | 0.0606 (18) | 0.0119 (15) | 0.0118 (15) | 0.0290 (15) |
F2B | 0.071 (4) | 0.123 (7) | 0.079 (5) | −0.041 (4) | −0.016 (3) | 0.066 (4) |
F3B | 0.090 (4) | 0.136 (6) | 0.144 (9) | 0.050 (5) | 0.031 (4) | 0.115 (6) |
F1B | 0.155 (11) | 0.116 (5) | 0.120 (8) | 0.060 (7) | 0.098 (7) | 0.055 (5) |
C16 | 0.0588 (17) | 0.092 (2) | 0.0617 (18) | 0.0173 (16) | 0.0045 (15) | 0.0339 (17) |
C20 | 0.068 (2) | 0.141 (3) | 0.098 (3) | 0.009 (2) | −0.012 (2) | 0.034 (2) |
C19 | 0.100 (2) | 0.085 (2) | 0.124 (3) | 0.053 (2) | 0.023 (2) | 0.012 (2) |
Geometric parameters (Å, º) top
C21—O1 | 1.409 (3) | C7—C12 | 1.390 (3) |
F1A—C6 | 1.266 (13) | C18—C13 | 1.378 (3) |
F2A—C6 | 1.323 (13) | C18—C17 | 1.373 (3) |
F3A—C6 | 1.306 (9) | C12—C11 | 1.363 (3) |
C4—C5 | 1.371 (3) | C10—C9 | 1.380 (4) |
C4—N3 | 1.371 (3) | C10—C11 | 1.384 (3) |
C4—C7 | 1.474 (3) | C13—C14 | 1.380 (3) |
N1—N2 | 1.338 (3) | C14—C15 | 1.387 (4) |
N1—C5 | 1.372 (3) | C14—C19 | 1.512 (4) |
N1—C13 | 1.442 (3) | C17—C16 | 1.374 (4) |
N2—N3 | 1.306 (3) | C15—C16 | 1.385 (4) |
C8—C7 | 1.387 (3) | C6—F2B | 1.267 (9) |
C8—C9 | 1.382 (3) | C6—F3B | 1.335 (11) |
O1—C10 | 1.370 (3) | C6—F1B | 1.318 (12) |
C5—C6 | 1.478 (4) | C16—C20 | 1.508 (4) |
| | | |
C5—C4—N3 | 107.1 (2) | C18—C13—N1 | 119.1 (2) |
C5—C4—C7 | 133.2 (2) | C18—C13—C14 | 122.1 (2) |
N3—C4—C7 | 119.7 (2) | C14—C13—N1 | 118.8 (2) |
N2—N1—C5 | 109.65 (19) | C13—C14—C15 | 116.1 (2) |
N2—N1—C13 | 119.69 (19) | C13—C14—C19 | 122.3 (2) |
C5—N1—C13 | 130.6 (2) | C15—C14—C19 | 121.6 (3) |
N3—N2—N1 | 108.13 (19) | C18—C17—C16 | 121.3 (3) |
C9—C8—C7 | 122.0 (2) | C16—C15—C14 | 123.7 (3) |
C10—O1—C21 | 118.5 (2) | F1A—C6—F2A | 106.8 (9) |
C4—C5—N1 | 105.5 (2) | F1A—C6—F3A | 108.6 (9) |
C4—C5—C6 | 131.9 (2) | F1A—C6—C5 | 114.0 (7) |
N1—C5—C6 | 122.5 (2) | F2A—C6—C5 | 112.4 (7) |
N2—N3—C4 | 109.6 (2) | F3A—C6—F2A | 102.4 (8) |
C8—C7—C4 | 118.6 (2) | F3A—C6—C5 | 111.8 (6) |
C8—C7—C12 | 117.6 (2) | F2B—C6—C5 | 116.0 (5) |
C12—C7—C4 | 123.7 (2) | F2B—C6—F3B | 105.5 (7) |
C17—C18—C13 | 119.5 (2) | F2B—C6—F1B | 108.6 (8) |
C11—C12—C7 | 121.1 (2) | F3B—C6—C5 | 109.9 (7) |
O1—C10—C9 | 124.1 (2) | F1B—C6—C5 | 111.7 (7) |
O1—C10—C11 | 116.1 (2) | F1B—C6—F3B | 104.2 (9) |
C9—C10—C11 | 119.8 (2) | C17—C16—C15 | 117.4 (3) |
C10—C9—C8 | 119.0 (2) | C17—C16—C20 | 121.7 (3) |
C12—C11—C10 | 120.6 (2) | C15—C16—C20 | 120.9 (3) |
| | | |
C21—O1—C10—C9 | −0.1 (4) | C5—N1—C13—C18 | −81.6 (3) |
C21—O1—C10—C11 | 179.5 (3) | C5—N1—C13—C14 | 99.6 (3) |
C4—C5—C6—F1A | 6.5 (13) | N3—C4—C5—N1 | 0.0 (2) |
C4—C5—C6—F2A | −115.3 (11) | N3—C4—C5—C6 | −176.1 (2) |
C4—C5—C6—F3A | 130.2 (9) | N3—C4—C7—C8 | 41.1 (3) |
C4—C5—C6—F2B | 152.2 (9) | N3—C4—C7—C12 | −136.1 (3) |
C4—C5—C6—F3B | 32.6 (9) | C7—C4—C5—N1 | 178.6 (2) |
C4—C5—C6—F1B | −82.6 (11) | C7—C4—C5—C6 | 2.5 (4) |
C4—C7—C12—C11 | 178.3 (2) | C7—C4—N3—N2 | −178.6 (2) |
N1—N2—N3—C4 | −0.4 (3) | C7—C8—C9—C10 | −0.8 (4) |
N1—C5—C6—F1A | −169.0 (13) | C7—C12—C11—C10 | −1.1 (4) |
N1—C5—C6—F2A | 69.2 (11) | C18—C13—C14—C15 | −0.3 (4) |
N1—C5—C6—F3A | −45.3 (9) | C18—C13—C14—C19 | 178.5 (3) |
N1—C5—C6—F2B | −23.3 (9) | C18—C17—C16—C15 | 1.4 (5) |
N1—C5—C6—F3B | −142.9 (8) | C18—C17—C16—C20 | −178.9 (3) |
N1—C5—C6—F1B | 101.9 (11) | C9—C8—C7—C4 | −177.5 (2) |
N1—C13—C14—C15 | 178.5 (2) | C9—C8—C7—C12 | −0.1 (4) |
N1—C13—C14—C19 | −2.7 (4) | C9—C10—C11—C12 | 0.1 (4) |
N2—N1—C5—C4 | −0.2 (2) | C11—C10—C9—C8 | 0.8 (4) |
N2—N1—C5—C6 | 176.3 (2) | C13—N1—N2—N3 | 178.3 (2) |
N2—N1—C13—C18 | 100.9 (3) | C13—N1—C5—C4 | −177.9 (2) |
N2—N1—C13—C14 | −77.9 (3) | C13—N1—C5—C6 | −1.3 (4) |
C8—C7—C12—C11 | 1.1 (4) | C13—C18—C17—C16 | −1.1 (4) |
O1—C10—C9—C8 | −179.7 (2) | C13—C14—C15—C16 | 0.7 (5) |
O1—C10—C11—C12 | −179.5 (2) | C14—C15—C16—C17 | −1.3 (5) |
C5—C4—N3—N2 | 0.3 (3) | C14—C15—C16—C20 | 179.0 (3) |
C5—C4—C7—C8 | −137.4 (3) | C17—C18—C13—N1 | −178.3 (2) |
C5—C4—C7—C12 | 45.4 (4) | C17—C18—C13—C14 | 0.5 (4) |
C5—N1—N2—N3 | 0.4 (3) | C19—C14—C15—C16 | −178.1 (3) |
1-[2,4-Bis(trifluoromethyl)phenyl]-4-(3-methoxyphenyl)-5-trifluoromethyl-1
H-1,2,3-triazole (5_C18H10F9N3O_abc13)
top
Crystal data top
C18H10F9N3O | F(000) = 912 |
Mr = 455.29 | Dx = 1.614 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9633 (8) Å | Cell parameters from 4121 reflections |
b = 7.8453 (5) Å | θ = 3.1–22.9° |
c = 20.0446 (14) Å | µ = 0.16 mm−1 |
β = 95.191 (1)° | T = 296 K |
V = 1873.6 (2) Å3 | Prism, colourless |
Z = 4 | 0.52 × 0.20 × 0.13 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.040 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
phi and ω scans | h = −14→14 |
16580 measured reflections | k = −9→9 |
3688 independent reflections | l = −24→24 |
2142 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.098P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
3688 reflections | Δρmax = 0.13 e Å−3 |
365 parameters | Δρmin = −0.17 e Å−3 |
484 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F1A | 0.3825 (6) | 0.3118 (13) | −0.0220 (5) | 0.095 (2) | 0.626 (15) |
F2A | 0.2105 (5) | 0.3767 (8) | −0.0419 (4) | 0.1102 (17) | 0.626 (15) |
F3A | 0.3308 (10) | 0.4986 (6) | −0.09522 (19) | 0.113 (3) | 0.626 (15) |
F7B | 0.3743 (5) | 1.0807 (6) | −0.28047 (18) | 0.136 (2) | 0.734 (8) |
F8B | 0.2181 (2) | 1.1783 (5) | −0.26167 (19) | 0.1004 (15) | 0.734 (8) |
F9B | 0.3667 (4) | 1.3003 (5) | −0.21996 (18) | 0.1081 (17) | 0.734 (8) |
F4A | 0.0987 (6) | 0.6882 (8) | −0.0612 (6) | 0.134 (2) | 0.620 (16) |
F6B | 0.0334 (6) | 0.9334 (10) | −0.0899 (4) | 0.111 (2) | 0.620 (16) |
F5A | 0.1185 (5) | 0.8984 (18) | 0.0042 (2) | 0.136 (3) | 0.620 (16) |
O1 | 0.46377 (12) | 0.29856 (19) | 0.29415 (7) | 0.0758 (4) | |
N1 | 0.33818 (12) | 0.74393 (19) | 0.00276 (7) | 0.0501 (4) | |
N2 | 0.35630 (14) | 0.8316 (2) | 0.06057 (8) | 0.0621 (4) | |
N3 | 0.35712 (14) | 0.7222 (2) | 0.10989 (7) | 0.0610 (4) | |
C4 | 0.33866 (14) | 0.5615 (2) | 0.08472 (9) | 0.0489 (4) | |
C5 | 0.32760 (14) | 0.5742 (2) | 0.01598 (9) | 0.0487 (4) | |
C6 | 0.3174 (2) | 0.4433 (3) | −0.03777 (11) | 0.0657 (6) | |
C7 | 0.33157 (15) | 0.4170 (2) | 0.13091 (9) | 0.0501 (4) | |
C8 | 0.40093 (15) | 0.4144 (2) | 0.19032 (9) | 0.0513 (5) | |
H8 | 0.454350 | 0.499710 | 0.198705 | 0.062* | |
C9 | 0.39184 (15) | 0.2869 (2) | 0.23727 (9) | 0.0534 (5) | |
C10 | 0.31385 (18) | 0.1596 (3) | 0.22494 (11) | 0.0677 (6) | |
H10 | 0.307093 | 0.073612 | 0.256262 | 0.081* | |
C11 | 0.2457 (2) | 0.1606 (3) | 0.16566 (12) | 0.0827 (7) | |
H11 | 0.193608 | 0.073546 | 0.157030 | 0.099* | |
C12 | 0.25323 (18) | 0.2876 (3) | 0.11909 (11) | 0.0717 (6) | |
H12 | 0.205832 | 0.286856 | 0.079671 | 0.086* | |
C13 | 0.33133 (15) | 0.8405 (2) | −0.05893 (8) | 0.0485 (4) | |
C14 | 0.22819 (15) | 0.9007 (2) | −0.08746 (9) | 0.0514 (5) | |
C15 | 0.22641 (16) | 1.0011 (2) | −0.14440 (9) | 0.0553 (5) | |
H15 | 0.158391 | 1.041789 | −0.164324 | 0.066* | |
C16 | 0.32444 (17) | 1.0409 (2) | −0.17166 (9) | 0.0535 (5) | |
C17 | 0.42625 (17) | 0.9818 (3) | −0.14259 (10) | 0.0597 (5) | |
H17 | 0.492424 | 1.009808 | −0.161049 | 0.072* | |
C18 | 0.42920 (16) | 0.8810 (3) | −0.08594 (9) | 0.0580 (5) | |
H18 | 0.497443 | 0.840753 | −0.066171 | 0.070* | |
C19 | 0.4509 (2) | 0.1815 (3) | 0.34683 (11) | 0.0865 (7) | |
H19A | 0.461358 | 0.067508 | 0.331159 | 0.130* | |
H19B | 0.376924 | 0.192423 | 0.361352 | 0.130* | |
H19C | 0.505663 | 0.205420 | 0.383647 | 0.130* | |
C20 | 0.3220 (2) | 1.1516 (3) | −0.23262 (12) | 0.0724 (6) | |
C21 | 0.1204 (2) | 0.8655 (4) | −0.05801 (13) | 0.0787 (7) | |
F1B | 0.3421 (19) | 0.295 (2) | −0.0180 (8) | 0.126 (5) | 0.374 (15) |
F2B | 0.2263 (7) | 0.430 (2) | −0.0729 (7) | 0.111 (4) | 0.374 (15) |
F3B | 0.3927 (11) | 0.4804 (17) | −0.0852 (7) | 0.129 (4) | 0.374 (15) |
F9A | 0.2730 (18) | 1.2947 (14) | −0.2183 (5) | 0.175 (8) | 0.266 (8) |
F8A | 0.2848 (15) | 1.0999 (14) | −0.2817 (4) | 0.130 (6) | 0.266 (8) |
F7A | 0.4276 (10) | 1.1975 (19) | −0.2463 (5) | 0.146 (5) | 0.266 (8) |
F5B | 0.1142 (11) | 1.002 (2) | −0.0109 (9) | 0.156 (5) | 0.380 (16) |
F6A | 0.0349 (9) | 0.886 (3) | −0.0992 (7) | 0.146 (5) | 0.380 (16) |
F4B | 0.1114 (8) | 0.743 (2) | −0.0248 (8) | 0.117 (4) | 0.380 (16) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1A | 0.121 (3) | 0.075 (4) | 0.083 (3) | 0.050 (3) | −0.019 (2) | −0.022 (2) |
F2A | 0.119 (3) | 0.112 (3) | 0.093 (4) | −0.027 (2) | −0.027 (2) | −0.038 (3) |
F3A | 0.231 (7) | 0.070 (2) | 0.0372 (17) | 0.012 (4) | 0.008 (3) | −0.0027 (13) |
F7B | 0.201 (5) | 0.149 (3) | 0.066 (2) | 0.067 (3) | 0.059 (3) | 0.0319 (19) |
F8B | 0.0919 (18) | 0.116 (3) | 0.089 (3) | 0.0009 (14) | −0.0169 (14) | 0.051 (2) |
F9B | 0.154 (3) | 0.075 (2) | 0.090 (2) | −0.049 (2) | −0.018 (2) | 0.0219 (16) |
F4A | 0.090 (2) | 0.107 (3) | 0.212 (7) | −0.012 (2) | 0.052 (4) | 0.018 (4) |
F6B | 0.063 (3) | 0.152 (4) | 0.120 (4) | 0.054 (3) | 0.019 (3) | 0.055 (3) |
F5A | 0.092 (3) | 0.258 (9) | 0.061 (2) | 0.029 (5) | 0.0281 (17) | 0.005 (4) |
O1 | 0.0770 (10) | 0.0879 (11) | 0.0597 (9) | −0.0165 (8) | −0.0098 (7) | 0.0242 (8) |
N1 | 0.0573 (9) | 0.0505 (9) | 0.0413 (8) | 0.0033 (7) | −0.0026 (7) | −0.0011 (7) |
N2 | 0.0835 (12) | 0.0543 (10) | 0.0473 (9) | −0.0026 (8) | −0.0007 (8) | −0.0043 (9) |
N3 | 0.0828 (12) | 0.0541 (10) | 0.0449 (9) | −0.0029 (8) | 0.0002 (8) | −0.0006 (8) |
C4 | 0.0497 (10) | 0.0519 (11) | 0.0443 (10) | 0.0009 (8) | −0.0007 (8) | −0.0011 (9) |
C5 | 0.0530 (10) | 0.0460 (11) | 0.0458 (10) | 0.0032 (8) | −0.0033 (8) | −0.0010 (9) |
C6 | 0.0861 (17) | 0.0556 (14) | 0.0523 (14) | 0.0058 (12) | −0.0110 (12) | −0.0035 (11) |
C7 | 0.0514 (10) | 0.0514 (11) | 0.0472 (10) | −0.0014 (9) | 0.0027 (8) | −0.0001 (9) |
C8 | 0.0522 (10) | 0.0517 (11) | 0.0499 (10) | −0.0047 (9) | 0.0032 (8) | 0.0006 (9) |
C9 | 0.0514 (11) | 0.0592 (12) | 0.0496 (11) | −0.0009 (9) | 0.0047 (9) | 0.0051 (10) |
C10 | 0.0733 (14) | 0.0628 (13) | 0.0668 (14) | −0.0126 (11) | 0.0058 (11) | 0.0134 (11) |
C11 | 0.0913 (17) | 0.0748 (16) | 0.0792 (16) | −0.0364 (13) | −0.0076 (13) | 0.0092 (13) |
C12 | 0.0747 (14) | 0.0743 (15) | 0.0630 (13) | −0.0171 (12) | −0.0113 (11) | 0.0042 (12) |
C13 | 0.0571 (11) | 0.0463 (10) | 0.0415 (10) | 0.0034 (8) | 0.0013 (8) | 0.0006 (8) |
C14 | 0.0544 (11) | 0.0547 (11) | 0.0448 (10) | 0.0106 (9) | 0.0030 (8) | −0.0008 (9) |
C15 | 0.0627 (12) | 0.0542 (12) | 0.0478 (11) | 0.0139 (9) | −0.0018 (9) | −0.0031 (9) |
C16 | 0.0728 (13) | 0.0434 (11) | 0.0437 (10) | 0.0020 (9) | 0.0017 (9) | −0.0037 (9) |
C17 | 0.0627 (12) | 0.0616 (13) | 0.0553 (12) | −0.0064 (10) | 0.0079 (9) | −0.0001 (10) |
C18 | 0.0530 (12) | 0.0638 (13) | 0.0563 (12) | 0.0044 (9) | 0.0000 (9) | 0.0024 (10) |
C19 | 0.0921 (17) | 0.0991 (19) | 0.0667 (14) | −0.0047 (14) | −0.0013 (12) | 0.0309 (14) |
C20 | 0.1018 (19) | 0.0600 (15) | 0.0547 (14) | −0.0037 (14) | 0.0041 (13) | 0.0019 (12) |
C21 | 0.0638 (15) | 0.106 (2) | 0.0676 (16) | 0.0233 (14) | 0.0104 (12) | 0.0208 (16) |
F1B | 0.252 (15) | 0.049 (3) | 0.069 (4) | 0.024 (8) | −0.029 (8) | −0.008 (3) |
F2B | 0.078 (4) | 0.164 (8) | 0.083 (6) | 0.026 (4) | −0.030 (4) | −0.058 (5) |
F3B | 0.145 (7) | 0.133 (6) | 0.123 (7) | −0.034 (5) | 0.086 (5) | −0.057 (5) |
F9A | 0.360 (19) | 0.076 (7) | 0.093 (7) | 0.084 (11) | 0.049 (11) | 0.031 (6) |
F8A | 0.214 (14) | 0.117 (9) | 0.051 (5) | −0.064 (10) | −0.027 (8) | 0.002 (5) |
F7A | 0.170 (7) | 0.169 (12) | 0.097 (7) | −0.086 (7) | 0.008 (5) | 0.042 (7) |
F5B | 0.124 (6) | 0.168 (9) | 0.192 (9) | −0.023 (6) | 0.102 (6) | −0.075 (7) |
F6A | 0.049 (5) | 0.272 (13) | 0.111 (6) | −0.041 (6) | −0.021 (4) | 0.054 (7) |
F4B | 0.068 (4) | 0.129 (8) | 0.160 (10) | 0.025 (5) | 0.045 (6) | 0.078 (7) |
Geometric parameters (Å, º) top
F1A—C6 | 1.315 (8) | C6—F3B | 1.398 (8) |
F2A—C6 | 1.376 (6) | C7—C8 | 1.389 (2) |
F3A—C6 | 1.254 (5) | C7—C12 | 1.387 (3) |
F7B—C20 | 1.315 (4) | C8—C9 | 1.384 (2) |
F8B—C20 | 1.341 (4) | C9—C10 | 1.374 (3) |
F9B—C20 | 1.299 (4) | C10—C11 | 1.379 (3) |
F4A—C21 | 1.415 (7) | C11—C12 | 1.374 (3) |
F6B—C21 | 1.286 (6) | C13—C14 | 1.395 (2) |
F5A—C21 | 1.275 (6) | C13—C18 | 1.371 (3) |
O1—C9 | 1.368 (2) | C14—C15 | 1.385 (2) |
O1—C19 | 1.418 (2) | C14—C21 | 1.492 (3) |
N1—N2 | 1.3481 (19) | C15—C16 | 1.374 (3) |
N1—C5 | 1.366 (2) | C16—C17 | 1.382 (3) |
N1—C13 | 1.446 (2) | C16—C20 | 1.497 (3) |
N2—N3 | 1.308 (2) | C17—C18 | 1.381 (3) |
N3—C4 | 1.369 (2) | C20—F9A | 1.311 (9) |
C4—C5 | 1.376 (2) | C20—F8A | 1.118 (7) |
C4—C7 | 1.471 (2) | C20—F7A | 1.365 (10) |
C5—C6 | 1.485 (3) | C21—F5B | 1.436 (9) |
C6—F1B | 1.253 (14) | C21—F6A | 1.264 (10) |
C6—F2B | 1.247 (7) | C21—F4B | 1.181 (9) |
| | | |
C9—O1—C19 | 118.36 (17) | C18—C13—N1 | 118.35 (15) |
N2—N1—C5 | 109.94 (14) | C18—C13—C14 | 120.98 (17) |
N2—N1—C13 | 117.40 (15) | C13—C14—C21 | 122.64 (18) |
C5—N1—C13 | 132.64 (15) | C15—C14—C13 | 118.53 (17) |
N3—N2—N1 | 107.74 (14) | C15—C14—C21 | 118.81 (18) |
N2—N3—C4 | 109.61 (14) | C16—C15—C14 | 120.45 (17) |
N3—C4—C5 | 107.47 (16) | C15—C16—C17 | 120.52 (17) |
N3—C4—C7 | 119.64 (15) | C15—C16—C20 | 120.14 (19) |
C5—C4—C7 | 132.87 (17) | C17—C16—C20 | 119.3 (2) |
N1—C5—C4 | 105.23 (15) | C18—C17—C16 | 119.64 (18) |
N1—C5—C6 | 122.43 (17) | C13—C18—C17 | 119.88 (18) |
C4—C5—C6 | 132.11 (18) | F7B—C20—F8B | 103.5 (3) |
F1A—C6—F2A | 104.1 (5) | F7B—C20—C16 | 112.0 (2) |
F1A—C6—C5 | 111.1 (5) | F8B—C20—C16 | 113.2 (2) |
F2A—C6—C5 | 108.8 (3) | F9B—C20—F7B | 107.9 (3) |
F3A—C6—F1A | 111.8 (6) | F9B—C20—F8B | 107.1 (3) |
F3A—C6—F2A | 105.7 (3) | F9B—C20—C16 | 112.6 (2) |
F3A—C6—C5 | 114.7 (3) | F9A—C20—C16 | 107.1 (4) |
F1B—C6—C5 | 114.2 (8) | F9A—C20—F7A | 105.0 (9) |
F1B—C6—F3B | 105.0 (9) | F8A—C20—C16 | 119.0 (5) |
F2B—C6—C5 | 118.4 (4) | F8A—C20—F9A | 110.7 (9) |
F2B—C6—F1B | 105.8 (9) | F8A—C20—F7A | 102.8 (7) |
F2B—C6—F3B | 102.6 (5) | F7A—C20—C16 | 111.5 (4) |
F3B—C6—C5 | 109.5 (5) | F4A—C21—C14 | 109.0 (4) |
C8—C7—C4 | 119.15 (17) | F6B—C21—F4A | 104.4 (5) |
C12—C7—C4 | 122.20 (17) | F6B—C21—C14 | 114.6 (4) |
C12—C7—C8 | 118.54 (17) | F5A—C21—F4A | 102.9 (5) |
C9—C8—C7 | 121.06 (17) | F5A—C21—F6B | 108.5 (5) |
O1—C9—C8 | 115.87 (17) | F5A—C21—C14 | 116.2 (4) |
O1—C9—C10 | 124.34 (18) | F5B—C21—C14 | 102.7 (5) |
C10—C9—C8 | 119.79 (18) | F6A—C21—C14 | 113.3 (7) |
C9—C10—C11 | 119.3 (2) | F6A—C21—F5B | 104.5 (8) |
C12—C11—C10 | 121.3 (2) | F4B—C21—C14 | 120.0 (4) |
C11—C12—C7 | 119.97 (19) | F4B—C21—F5B | 103.0 (6) |
C14—C13—N1 | 120.52 (16) | F4B—C21—F6A | 111.1 (9) |
1-(3,4-Dimethoxyphenyl)-4-(3,4-dimethoxyphenyl)-5-trifluoromethyl-1
H-1,2,3-triazole (6_C19H18F3N3O4_ABC23)
top
Crystal data top
C19H18F3N3O4 | F(000) = 848 |
Mr = 409.36 | Dx = 1.391 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 30.656 (2) Å | Cell parameters from 3310 reflections |
b = 8.3363 (6) Å | θ = 2.5–22.8° |
c = 7.6723 (6) Å | µ = 0.12 mm−1 |
β = 94.627 (1)° | T = 293 K |
V = 1954.3 (3) Å3 | Prismatic, colorless |
Z = 4 | 0.41 × 0.29 × 0.09 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.049 |
phi and ω scans | θmax = 25.5°, θmin = 1.3° |
16559 measured reflections | h = −37→37 |
3634 independent reflections | k = −10→10 |
1881 reflections with I > 2σ(I) | l = −9→9 |
Refinement top
Refinement on F2 | 36 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1371P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3634 reflections | Δρmax = 0.14 e Å−3 |
289 parameters | Δρmin = −0.13 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F2A | 0.2870 (3) | 0.3129 (14) | 0.2864 (16) | 0.134 (4) | 0.7 |
F3A | 0.22126 (15) | 0.2948 (10) | 0.3284 (11) | 0.111 (3) | 0.7 |
F1A | 0.2596 (2) | 0.4880 (9) | 0.4359 (8) | 0.158 (3) | 0.7 |
F2B | 0.2885 (6) | 0.357 (3) | 0.338 (3) | 0.106 (8) | 0.3 |
F3B | 0.2256 (6) | 0.260 (3) | 0.272 (3) | 0.135 (8) | 0.3 |
F1B | 0.2339 (3) | 0.4560 (17) | 0.4402 (16) | 0.089 (4) | 0.3 |
C21 | 0.00296 (8) | 0.2878 (4) | 0.1042 (4) | 0.0729 (8) | |
H21A | −0.024987 | 0.277532 | 0.151248 | 0.109* | |
H21B | −0.000800 | 0.336655 | −0.009313 | 0.109* | |
H21C | 0.015824 | 0.183513 | 0.094428 | 0.109* | |
C22 | 0.10824 (10) | 0.6225 (4) | 0.5701 (4) | 0.0926 (11) | |
H22A | 0.091879 | 0.644599 | 0.668942 | 0.139* | |
H22B | 0.133474 | 0.559165 | 0.606916 | 0.139* | |
H22C | 0.117444 | 0.721630 | 0.521047 | 0.139* | |
C19 | 0.38750 (10) | 0.3769 (5) | −0.3573 (4) | 0.1066 (12) | |
H19A | 0.408395 | 0.342779 | −0.436377 | 0.160* | |
H19B | 0.371110 | 0.285849 | −0.322403 | 0.160* | |
H19C | 0.367917 | 0.453771 | −0.414532 | 0.160* | |
C20 | 0.47877 (9) | 0.6290 (5) | 0.2087 (5) | 0.1183 (14) | |
H20A | 0.509219 | 0.620553 | 0.189121 | 0.177* | |
H20B | 0.471363 | 0.739649 | 0.224605 | 0.177* | |
H20C | 0.473104 | 0.569331 | 0.311511 | 0.177* | |
O1 | 0.08186 (5) | 0.5380 (2) | 0.4439 (2) | 0.0581 (5) | |
O2 | 0.03110 (4) | 0.3858 (2) | 0.2180 (2) | 0.0555 (5) | |
C8 | 0.14225 (7) | 0.5312 (3) | 0.2570 (3) | 0.0482 (6) | |
H8 | 0.160656 | 0.587718 | 0.337495 | 0.058* | |
C9 | 0.09994 (7) | 0.4962 (3) | 0.2936 (3) | 0.0427 (6) | |
N1A | 0.27051 (7) | 0.5588 (3) | 0.0331 (3) | 0.0521 (6) | 0.45 |
C4A | 0.20101 (6) | 0.5240 (3) | 0.0568 (3) | 0.0512 (6) | 0.45 |
C4B | 0.27051 (7) | 0.5588 (3) | 0.0331 (3) | 0.0521 (6) | 0.55 |
N1B | 0.20101 (6) | 0.5240 (3) | 0.0568 (3) | 0.0512 (6) | 0.55 |
O3 | 0.40974 (5) | 0.4479 (2) | −0.2079 (3) | 0.0781 (6) | |
C13 | 0.31806 (7) | 0.5609 (3) | 0.0491 (3) | 0.0527 (7) | |
C10 | 0.07240 (7) | 0.4131 (3) | 0.1707 (3) | 0.0448 (6) | |
O4 | 0.45308 (5) | 0.5661 (3) | 0.0623 (3) | 0.0861 (7) | |
N2 | 0.24820 (7) | 0.6257 (3) | −0.1071 (3) | 0.0694 (7) | |
C12 | 0.13043 (8) | 0.3983 (3) | −0.0189 (3) | 0.0576 (7) | |
H12 | 0.140840 | 0.364073 | −0.123250 | 0.069* | |
C11 | 0.08784 (7) | 0.3650 (3) | 0.0163 (3) | 0.0559 (7) | |
H11 | 0.069537 | 0.309429 | −0.065309 | 0.067* | |
C7 | 0.15721 (7) | 0.4819 (3) | 0.1001 (3) | 0.0473 (6) | |
C5 | 0.24118 (7) | 0.4937 (3) | 0.1386 (3) | 0.0488 (6) | |
N3 | 0.20629 (7) | 0.6058 (3) | −0.0935 (3) | 0.0688 (7) | |
C14 | 0.34016 (7) | 0.5020 (3) | −0.0884 (3) | 0.0525 (6) | |
H14 | 0.324414 | 0.460671 | −0.187031 | 0.063* | |
C16 | 0.40865 (8) | 0.5681 (3) | 0.0668 (4) | 0.0594 (7) | |
C15 | 0.38522 (8) | 0.5041 (3) | −0.0799 (3) | 0.0552 (7) | |
C18 | 0.34132 (8) | 0.6228 (3) | 0.1930 (4) | 0.0689 (8) | |
H18 | 0.326684 | 0.662158 | 0.285641 | 0.083* | |
C6 | 0.25045 (10) | 0.3951 (4) | 0.2961 (5) | 0.0694 (8) | |
C17 | 0.38671 (8) | 0.6273 (4) | 0.2017 (4) | 0.0730 (9) | |
H17 | 0.402323 | 0.670610 | 0.299480 | 0.088* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F2A | 0.079 (5) | 0.120 (5) | 0.206 (10) | 0.054 (4) | 0.042 (4) | 0.096 (6) |
F3A | 0.053 (2) | 0.131 (6) | 0.149 (7) | −0.006 (3) | 0.008 (2) | 0.095 (6) |
F1A | 0.248 (8) | 0.137 (4) | 0.083 (3) | −0.007 (6) | −0.026 (5) | 0.022 (3) |
F2B | 0.038 (7) | 0.152 (18) | 0.122 (10) | −0.007 (9) | −0.032 (7) | 0.067 (10) |
F3B | 0.198 (15) | 0.086 (7) | 0.121 (10) | −0.049 (8) | 0.011 (8) | 0.025 (6) |
F1B | 0.085 (6) | 0.125 (10) | 0.060 (5) | 0.034 (6) | 0.019 (5) | 0.019 (5) |
C21 | 0.0466 (15) | 0.090 (2) | 0.081 (2) | −0.0172 (14) | −0.0018 (14) | −0.0081 (17) |
C22 | 0.090 (2) | 0.126 (3) | 0.062 (2) | −0.034 (2) | 0.0058 (17) | −0.031 (2) |
C19 | 0.085 (2) | 0.159 (4) | 0.078 (2) | −0.015 (2) | 0.0207 (19) | −0.049 (2) |
C20 | 0.0512 (18) | 0.173 (4) | 0.129 (3) | −0.014 (2) | −0.0041 (19) | −0.059 (3) |
O1 | 0.0516 (10) | 0.0647 (12) | 0.0585 (11) | −0.0025 (8) | 0.0067 (9) | −0.0146 (9) |
O2 | 0.0363 (9) | 0.0678 (12) | 0.0624 (11) | −0.0073 (8) | 0.0036 (8) | −0.0056 (9) |
C8 | 0.0409 (13) | 0.0427 (15) | 0.0596 (17) | −0.0009 (10) | −0.0040 (12) | −0.0011 (12) |
C9 | 0.0396 (13) | 0.0387 (14) | 0.0498 (15) | 0.0066 (10) | 0.0031 (11) | −0.0003 (11) |
N1A | 0.0416 (13) | 0.0476 (14) | 0.0682 (17) | −0.0001 (10) | 0.0113 (12) | 0.0052 (12) |
C4A | 0.0418 (13) | 0.0480 (14) | 0.0650 (16) | 0.0016 (10) | 0.0107 (11) | 0.0107 (12) |
C4B | 0.0416 (13) | 0.0476 (14) | 0.0682 (17) | −0.0001 (10) | 0.0113 (12) | 0.0052 (12) |
N1B | 0.0418 (13) | 0.0480 (14) | 0.0650 (16) | 0.0016 (10) | 0.0107 (11) | 0.0107 (12) |
O3 | 0.0547 (11) | 0.1072 (16) | 0.0747 (14) | −0.0044 (10) | 0.0205 (10) | −0.0245 (12) |
C13 | 0.0430 (14) | 0.0465 (16) | 0.0698 (19) | −0.0043 (11) | 0.0112 (13) | −0.0003 (13) |
C10 | 0.0341 (13) | 0.0451 (15) | 0.0550 (16) | 0.0004 (10) | 0.0028 (11) | 0.0014 (12) |
O4 | 0.0410 (10) | 0.1157 (18) | 0.1023 (16) | −0.0095 (10) | 0.0108 (10) | −0.0308 (13) |
N2 | 0.0481 (13) | 0.0769 (17) | 0.0845 (18) | 0.0015 (12) | 0.0134 (12) | 0.0215 (14) |
C12 | 0.0500 (15) | 0.0644 (18) | 0.0597 (17) | −0.0005 (13) | 0.0127 (13) | −0.0089 (14) |
C11 | 0.0495 (15) | 0.0591 (17) | 0.0589 (17) | −0.0077 (12) | 0.0036 (13) | −0.0127 (13) |
C7 | 0.0364 (13) | 0.0448 (15) | 0.0609 (17) | 0.0052 (11) | 0.0050 (12) | 0.0027 (13) |
C5 | 0.0426 (14) | 0.0415 (14) | 0.0631 (17) | 0.0017 (11) | 0.0083 (12) | 0.0058 (13) |
N3 | 0.0489 (14) | 0.0799 (17) | 0.0783 (17) | 0.0028 (11) | 0.0104 (11) | 0.0222 (14) |
C14 | 0.0475 (15) | 0.0496 (16) | 0.0613 (17) | −0.0040 (11) | 0.0085 (12) | 0.0004 (13) |
C16 | 0.0401 (14) | 0.0642 (18) | 0.0746 (19) | −0.0068 (12) | 0.0094 (13) | −0.0107 (15) |
C15 | 0.0460 (15) | 0.0571 (17) | 0.0649 (18) | −0.0032 (12) | 0.0183 (13) | −0.0062 (14) |
C18 | 0.0550 (17) | 0.075 (2) | 0.080 (2) | −0.0080 (14) | 0.0225 (15) | −0.0204 (16) |
C6 | 0.055 (2) | 0.065 (2) | 0.088 (3) | 0.0046 (17) | 0.0057 (19) | 0.017 (2) |
C17 | 0.0534 (17) | 0.088 (2) | 0.079 (2) | −0.0133 (15) | 0.0124 (15) | −0.0280 (17) |
Geometric parameters (Å, º) top
F2A—C6 | 1.320 (11) | C4A—N3 | 1.360 (3) |
F3A—C6 | 1.264 (7) | C4B—C13 | 1.453 (3) |
F1A—C6 | 1.334 (7) | C4B—N2 | 1.348 (3) |
F2B—C6 | 1.227 (17) | C4B—C5 | 1.369 (3) |
F3B—C6 | 1.36 (2) | N1B—C7 | 1.452 (3) |
F1B—C6 | 1.351 (13) | N1B—C5 | 1.360 (3) |
C21—O2 | 1.433 (3) | N1B—N3 | 1.360 (3) |
C22—O1 | 1.400 (3) | O3—C15 | 1.366 (3) |
C19—O3 | 1.416 (3) | C13—C14 | 1.389 (3) |
C20—O4 | 1.420 (3) | C13—C18 | 1.367 (3) |
O1—C9 | 1.365 (3) | C10—C11 | 1.371 (3) |
O2—C10 | 1.364 (2) | O4—C16 | 1.365 (3) |
C8—C9 | 1.380 (3) | N2—N3 | 1.308 (2) |
C8—C7 | 1.385 (3) | C12—C11 | 1.383 (3) |
C9—C10 | 1.398 (3) | C12—C7 | 1.368 (3) |
N1A—C13 | 1.453 (3) | C5—C6 | 1.470 (4) |
N1A—N2 | 1.348 (3) | C14—C15 | 1.378 (3) |
N1A—C5 | 1.369 (3) | C16—C15 | 1.392 (3) |
C4A—C7 | 1.452 (3) | C16—C17 | 1.371 (3) |
C4A—C5 | 1.360 (3) | C18—C17 | 1.388 (3) |
| | | |
C9—O1—C22 | 117.50 (19) | C8—C7—N1B | 120.3 (2) |
C10—O2—C21 | 117.31 (18) | C12—C7—C8 | 120.6 (2) |
C9—C8—C7 | 119.7 (2) | C12—C7—C4A | 119.1 (2) |
O1—C9—C8 | 124.8 (2) | C12—C7—N1B | 119.1 (2) |
O1—C9—C10 | 115.61 (19) | N1A—C5—C6 | 127.9 (2) |
C8—C9—C10 | 119.6 (2) | C4A—C5—N1A | 105.5 (2) |
N2—N1A—C13 | 120.2 (2) | C4A—C5—C6 | 126.2 (2) |
N2—N1A—C5 | 108.70 (19) | C4B—C5—C6 | 127.9 (2) |
C5—N1A—C13 | 131.1 (2) | N1B—C5—C4B | 105.5 (2) |
C5—C4A—C7 | 132.0 (2) | N1B—C5—C6 | 126.2 (2) |
N3—C4A—C7 | 119.4 (2) | N2—N3—C4A | 108.44 (19) |
N3—C4A—C5 | 108.61 (19) | N2—N3—N1B | 108.44 (19) |
N2—C4B—C13 | 120.2 (2) | C15—C14—C13 | 120.5 (2) |
N2—C4B—C5 | 108.70 (19) | O4—C16—C15 | 115.2 (2) |
C5—C4B—C13 | 131.1 (2) | O4—C16—C17 | 125.1 (2) |
C5—N1B—C7 | 132.0 (2) | C17—C16—C15 | 119.7 (2) |
N3—N1B—C7 | 119.4 (2) | O3—C15—C14 | 124.7 (2) |
N3—N1B—C5 | 108.61 (19) | O3—C15—C16 | 115.7 (2) |
C15—O3—C19 | 117.9 (2) | C14—C15—C16 | 119.6 (2) |
C14—C13—N1A | 118.6 (2) | C13—C18—C17 | 120.3 (2) |
C14—C13—C4B | 118.6 (2) | F2A—C6—F1A | 102.9 (6) |
C18—C13—N1A | 121.8 (2) | F2A—C6—C5 | 110.6 (6) |
C18—C13—C4B | 121.8 (2) | F3A—C6—F2A | 106.5 (6) |
C18—C13—C14 | 119.5 (2) | F3A—C6—F1A | 109.4 (6) |
O2—C10—C9 | 115.2 (2) | F3A—C6—C5 | 116.0 (4) |
O2—C10—C11 | 125.0 (2) | F1A—C6—C5 | 110.5 (4) |
C11—C10—C9 | 119.7 (2) | F2B—C6—F3B | 109.2 (15) |
C16—O4—C20 | 117.8 (2) | F2B—C6—F1B | 107.0 (13) |
N3—N2—N1A | 108.77 (19) | F2B—C6—C5 | 118.7 (13) |
N3—N2—C4B | 108.77 (19) | F3B—C6—C5 | 106.4 (9) |
C7—C12—C11 | 119.8 (2) | F1B—C6—F3B | 100.2 (10) |
C10—C11—C12 | 120.5 (2) | F1B—C6—C5 | 113.7 (6) |
C8—C7—C4A | 120.3 (2) | C16—C17—C18 | 120.4 (3) |
| | | |
C21—O2—C10—C9 | −174.1 (2) | N2—C4B—C13—C18 | 125.0 (3) |
C21—O2—C10—C11 | 5.6 (3) | N2—C4B—C5—N1B | 0.0 (3) |
C22—O1—C9—C8 | 0.0 (3) | N2—C4B—C5—C6 | 173.5 (3) |
C22—O1—C9—C10 | −179.6 (2) | C11—C12—C7—C8 | 1.0 (4) |
C19—O3—C15—C14 | −2.5 (4) | C11—C12—C7—C4A | −176.5 (2) |
C19—O3—C15—C16 | 178.0 (3) | C11—C12—C7—N1B | −176.5 (2) |
C20—O4—C16—C15 | −179.6 (3) | C7—C8—C9—O1 | 179.6 (2) |
C20—O4—C16—C17 | 0.5 (4) | C7—C8—C9—C10 | −0.8 (3) |
O1—C9—C10—O2 | 0.3 (3) | C7—C4A—C5—N1A | 178.0 (2) |
O1—C9—C10—C11 | −179.4 (2) | C7—C4A—C5—C6 | 4.4 (4) |
O2—C10—C11—C12 | −179.8 (2) | C7—C4A—N3—N2 | −178.1 (2) |
C8—C9—C10—O2 | −179.30 (19) | C7—N1B—C5—C4B | 178.0 (2) |
C8—C9—C10—C11 | 1.0 (3) | C7—N1B—C5—C6 | 4.4 (4) |
C9—C8—C7—C4A | 177.3 (2) | C7—N1B—N3—N2 | −178.1 (2) |
C9—C8—C7—N1B | 177.3 (2) | C7—C12—C11—C10 | −0.9 (4) |
C9—C8—C7—C12 | −0.2 (3) | C5—N1A—C13—C14 | 124.8 (3) |
C9—C10—C11—C12 | −0.1 (4) | C5—N1A—C13—C18 | −56.9 (4) |
N1A—C13—C14—C15 | 179.0 (2) | C5—N1A—N2—N3 | 0.2 (3) |
N1A—C13—C18—C17 | −178.1 (2) | C5—C4A—C7—C8 | 58.8 (4) |
N1A—N2—N3—C4A | −0.4 (3) | C5—C4A—C7—C12 | −123.7 (3) |
C4B—C13—C14—C15 | 179.0 (2) | C5—C4A—N3—N2 | 0.4 (3) |
C4B—C13—C18—C17 | −178.1 (2) | C5—C4B—C13—C14 | 124.8 (3) |
C4B—N2—N3—N1B | −0.4 (3) | C5—C4B—C13—C18 | −56.9 (4) |
C13—N1A—N2—N3 | 178.7 (2) | C5—C4B—N2—N3 | 0.2 (3) |
C13—N1A—C5—C4A | −178.2 (2) | C5—N1B—C7—C8 | 58.8 (4) |
C13—N1A—C5—C6 | −4.8 (5) | C5—N1B—C7—C12 | −123.7 (3) |
C13—C4B—N2—N3 | 178.7 (2) | C5—N1B—N3—N2 | 0.4 (3) |
C13—C4B—C5—N1B | −178.2 (2) | N3—C4A—C7—C8 | −123.1 (3) |
C13—C4B—C5—C6 | −4.8 (5) | N3—C4A—C7—C12 | 54.4 (3) |
C13—C14—C15—O3 | 179.6 (2) | N3—C4A—C5—N1A | −0.2 (3) |
C13—C14—C15—C16 | −0.9 (4) | N3—C4A—C5—C6 | −173.8 (3) |
C13—C18—C17—C16 | −0.7 (4) | N3—N1B—C7—C8 | −123.1 (3) |
O4—C16—C15—O3 | 0.1 (3) | N3—N1B—C7—C12 | 54.4 (3) |
O4—C16—C15—C14 | −179.4 (2) | N3—N1B—C5—C4B | −0.2 (3) |
O4—C16—C17—C18 | −179.8 (3) | N3—N1B—C5—C6 | −173.8 (3) |
N2—N1A—C13—C14 | −53.3 (3) | C14—C13—C18—C17 | 0.2 (4) |
N2—N1A—C13—C18 | 125.0 (3) | C15—C16—C17—C18 | 0.3 (4) |
N2—N1A—C5—C4A | 0.0 (3) | C18—C13—C14—C15 | 0.6 (4) |
N2—N1A—C5—C6 | 173.5 (3) | C17—C16—C15—O3 | −180.0 (2) |
N2—C4B—C13—C14 | −53.3 (3) | C17—C16—C15—C14 | 0.5 (4) |
3-[4-(3,4-Dimethoxyphenyl)-5-(trifluoromethyl)-1
H-1,2,3-triazol-1-yl]phenol (7_C17H14F3N3O3)
top
Crystal data top
C17H14F3N3O3 | F(000) = 752 |
Mr = 365.31 | Dx = 1.499 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.267 (2) Å | Cell parameters from 1754 reflections |
b = 8.4334 (14) Å | θ = 2.6–20.7° |
c = 15.686 (3) Å | µ = 0.13 mm−1 |
β = 93.904 (3)° | T = 293 K |
V = 1619.0 (5) Å3 | Prismatic, colorless |
Z = 4 | 0.59 × 0.11 × 0.07 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.146 |
phi and ω scans | θmax = 26.0°, θmin = 1.7° |
14139 measured reflections | h = −15→15 |
3188 independent reflections | k = −10→10 |
1336 reflections with I > 2σ(I) | l = −19→19 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.189 | w = 1/[σ2(Fo2) + (0.0845P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
3188 reflections | Δρmax = 0.26 e Å−3 |
235 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C20 | 0.8329 (3) | −0.0079 (7) | 0.3176 (3) | 0.0541 (14) | |
H20A | 0.8974 | −0.0300 | 0.3536 | 0.081* | |
H20B | 0.7871 | 0.0645 | 0.3461 | 0.081* | |
H20C | 0.7937 | −0.1047 | 0.3054 | 0.081* | |
C19 | 0.9660 (4) | 0.2263 (7) | 0.0204 (3) | 0.0740 (19) | |
H19A | 1.0445 | 0.2267 | 0.0249 | 0.111* | |
H19B | 0.9404 | 0.1596 | −0.0264 | 0.111* | |
H19C | 0.9397 | 0.3323 | 0.0105 | 0.111* | |
F1 | 0.3156 (2) | 0.2140 (3) | 0.06978 (18) | 0.0623 (9) | |
F3 | 0.30635 (19) | 0.4482 (3) | 0.01740 (16) | 0.0558 (8) | |
F2 | 0.43554 (19) | 0.3871 (3) | 0.10946 (16) | 0.0560 (8) | |
N1 | 0.4142 (2) | 0.2988 (4) | −0.1121 (2) | 0.0298 (9) | |
N3 | 0.5783 (2) | 0.2093 (4) | −0.1062 (2) | 0.0343 (9) | |
O3 | 0.2226 (2) | 0.6087 (4) | −0.3331 (2) | 0.0562 (10) | |
H3 | 0.2850 | 0.6383 | −0.3401 | 0.067* | |
O2 | 0.8630 (2) | 0.0614 (4) | 0.23952 (17) | 0.0465 (9) | |
N2 | 0.4966 (2) | 0.2538 (4) | −0.1594 (2) | 0.0355 (9) | |
O1 | 0.9269 (2) | 0.1674 (4) | 0.09764 (19) | 0.0560 (10) | |
C9 | 0.8163 (3) | 0.1585 (5) | 0.1025 (3) | 0.0348 (11) | |
C5 | 0.4442 (3) | 0.2821 (5) | −0.0270 (3) | 0.0283 (10) | |
C11 | 0.6711 (3) | 0.0847 (5) | 0.1904 (3) | 0.0376 (11) | |
H11 | 0.6476 | 0.0467 | 0.2417 | 0.045* | |
C15 | 0.2243 (3) | 0.5046 (5) | −0.2670 (3) | 0.0352 (11) | |
C10 | 0.7820 (3) | 0.1010 (5) | 0.1802 (3) | 0.0347 (11) | |
C7 | 0.6277 (3) | 0.1829 (5) | 0.0482 (3) | 0.0304 (10) | |
C14 | 0.3199 (3) | 0.4599 (5) | −0.2209 (3) | 0.0324 (11) | |
H14 | 0.3868 | 0.5033 | −0.2332 | 0.039* | |
C12 | 0.5949 (3) | 0.1252 (5) | 0.1242 (3) | 0.0354 (11) | |
H12 | 0.5208 | 0.1129 | 0.1315 | 0.042* | |
C8 | 0.7407 (3) | 0.1984 (5) | 0.0379 (3) | 0.0337 (11) | |
H8 | 0.7640 | 0.2362 | −0.0135 | 0.040* | |
C18 | 0.2155 (3) | 0.2837 (5) | −0.1356 (3) | 0.0394 (12) | |
H18 | 0.2129 | 0.2092 | −0.0921 | 0.047* | |
C16 | 0.1246 (3) | 0.4426 (6) | −0.2464 (3) | 0.0432 (12) | |
H16 | 0.0603 | 0.4751 | −0.2761 | 0.052* | |
C4 | 0.5508 (3) | 0.2235 (5) | −0.0238 (3) | 0.0293 (10) | |
C6 | 0.3750 (3) | 0.3312 (6) | 0.0421 (3) | 0.0372 (11) | |
C13 | 0.3138 (3) | 0.3506 (5) | −0.1571 (2) | 0.0283 (10) | |
C17 | 0.1217 (3) | 0.3337 (6) | −0.1824 (3) | 0.0447 (13) | |
H17 | 0.0547 | 0.2915 | −0.1697 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C20 | 0.044 (3) | 0.084 (4) | 0.033 (3) | 0.006 (3) | −0.004 (2) | 0.022 (3) |
C19 | 0.028 (3) | 0.143 (6) | 0.053 (4) | −0.012 (3) | 0.011 (2) | 0.027 (4) |
F1 | 0.0571 (17) | 0.071 (2) | 0.063 (2) | −0.0048 (15) | 0.0358 (15) | 0.0066 (17) |
F3 | 0.0469 (16) | 0.070 (2) | 0.0505 (17) | 0.0315 (14) | 0.0032 (13) | −0.0029 (15) |
F2 | 0.0472 (16) | 0.081 (2) | 0.0382 (16) | 0.0115 (14) | −0.0073 (12) | −0.0202 (15) |
N1 | 0.0139 (16) | 0.048 (2) | 0.027 (2) | 0.0033 (15) | 0.0009 (14) | 0.0024 (18) |
N3 | 0.0168 (17) | 0.057 (3) | 0.029 (2) | 0.0028 (16) | −0.0017 (15) | 0.0025 (19) |
O3 | 0.0237 (16) | 0.088 (3) | 0.056 (2) | −0.0011 (16) | −0.0024 (14) | 0.029 (2) |
O2 | 0.0275 (16) | 0.080 (3) | 0.0314 (17) | 0.0019 (15) | −0.0021 (13) | 0.0190 (17) |
N2 | 0.0194 (17) | 0.057 (3) | 0.030 (2) | 0.0038 (16) | 0.0027 (16) | −0.0012 (18) |
O1 | 0.0181 (16) | 0.104 (3) | 0.046 (2) | −0.0025 (16) | 0.0031 (14) | 0.0230 (19) |
C9 | 0.020 (2) | 0.054 (3) | 0.031 (2) | 0.0016 (19) | 0.0020 (18) | 0.004 (2) |
C5 | 0.0159 (19) | 0.039 (3) | 0.030 (2) | 0.0034 (18) | 0.0021 (17) | −0.001 (2) |
C11 | 0.027 (2) | 0.059 (3) | 0.027 (2) | 0.004 (2) | 0.0041 (18) | 0.012 (2) |
C15 | 0.025 (2) | 0.050 (3) | 0.030 (2) | 0.003 (2) | −0.0001 (18) | 0.007 (2) |
C10 | 0.023 (2) | 0.048 (3) | 0.032 (2) | 0.002 (2) | −0.0029 (18) | 0.005 (2) |
C7 | 0.021 (2) | 0.039 (3) | 0.031 (2) | 0.0039 (18) | −0.0027 (18) | 0.001 (2) |
C14 | 0.016 (2) | 0.050 (3) | 0.031 (2) | −0.0018 (18) | −0.0024 (17) | 0.005 (2) |
C12 | 0.018 (2) | 0.051 (3) | 0.037 (3) | 0.0003 (19) | 0.0023 (18) | 0.007 (2) |
C8 | 0.019 (2) | 0.054 (3) | 0.028 (2) | −0.0006 (19) | 0.0043 (17) | 0.007 (2) |
C18 | 0.025 (2) | 0.053 (3) | 0.041 (3) | −0.001 (2) | 0.0003 (19) | 0.010 (2) |
C16 | 0.018 (2) | 0.065 (4) | 0.046 (3) | −0.002 (2) | −0.0045 (19) | 0.004 (3) |
C4 | 0.023 (2) | 0.036 (3) | 0.029 (2) | −0.0018 (18) | −0.0005 (18) | −0.003 (2) |
C6 | 0.033 (2) | 0.046 (3) | 0.033 (3) | 0.006 (2) | 0.007 (2) | 0.001 (2) |
C13 | 0.015 (2) | 0.045 (3) | 0.025 (2) | 0.0034 (18) | −0.0009 (16) | 0.001 (2) |
C17 | 0.017 (2) | 0.062 (4) | 0.055 (3) | −0.001 (2) | 0.004 (2) | 0.006 (3) |
Geometric parameters (Å, º) top
C20—H20A | 0.9600 | C9—C8 | 1.369 (5) |
C20—H20B | 0.9600 | C5—C4 | 1.396 (5) |
C20—H20C | 0.9600 | C5—C6 | 1.480 (5) |
C20—O2 | 1.428 (5) | C11—H11 | 0.9300 |
C19—H19A | 0.9600 | C11—C10 | 1.388 (5) |
C19—H19B | 0.9600 | C11—C12 | 1.392 (5) |
C19—H19C | 0.9600 | C15—C14 | 1.388 (5) |
C19—O1 | 1.423 (5) | C15—C16 | 1.388 (5) |
F1—C6 | 1.319 (5) | C7—C12 | 1.373 (5) |
F3—C6 | 1.337 (5) | C7—C8 | 1.413 (5) |
F2—C6 | 1.336 (5) | C7—C4 | 1.461 (5) |
N1—N2 | 1.349 (4) | C14—H14 | 0.9300 |
N1—C5 | 1.368 (5) | C14—C13 | 1.366 (5) |
N1—C13 | 1.446 (5) | C12—H12 | 0.9300 |
N3—N2 | 1.315 (4) | C8—H8 | 0.9300 |
N3—C4 | 1.363 (5) | C18—H18 | 0.9300 |
O3—H3 | 0.8200 | C18—C13 | 1.393 (5) |
O3—C15 | 1.357 (5) | C18—C17 | 1.388 (6) |
O2—C10 | 1.356 (4) | C16—H16 | 0.9300 |
O1—C9 | 1.366 (4) | C16—C17 | 1.362 (6) |
C9—C10 | 1.402 (6) | C17—H17 | 0.9300 |
| | | |
H20A—C20—H20B | 109.5 | C11—C10—C9 | 119.3 (4) |
H20A—C20—H20C | 109.5 | C12—C7—C8 | 118.6 (4) |
H20B—C20—H20C | 109.5 | C12—C7—C4 | 122.8 (3) |
O2—C20—H20A | 109.5 | C8—C7—C4 | 118.5 (4) |
O2—C20—H20B | 109.5 | C15—C14—H14 | 120.7 |
O2—C20—H20C | 109.5 | C13—C14—C15 | 118.6 (4) |
H19A—C19—H19B | 109.5 | C13—C14—H14 | 120.7 |
H19A—C19—H19C | 109.5 | C11—C12—H12 | 119.5 |
H19B—C19—H19C | 109.5 | C7—C12—C11 | 120.9 (4) |
O1—C19—H19A | 109.5 | C7—C12—H12 | 119.5 |
O1—C19—H19B | 109.5 | C9—C8—C7 | 120.9 (4) |
O1—C19—H19C | 109.5 | C9—C8—H8 | 119.5 |
N2—N1—C5 | 110.3 (3) | C7—C8—H8 | 119.5 |
N2—N1—C13 | 117.5 (3) | C13—C18—H18 | 121.7 |
C5—N1—C13 | 132.2 (3) | C17—C18—H18 | 121.7 |
N2—N3—C4 | 110.5 (3) | C17—C18—C13 | 116.7 (4) |
C15—O3—H3 | 109.5 | C15—C16—H16 | 120.2 |
C10—O2—C20 | 117.9 (3) | C17—C16—C15 | 119.6 (4) |
N3—N2—N1 | 107.3 (3) | C17—C16—H16 | 120.2 |
C9—O1—C19 | 117.4 (3) | N3—C4—C5 | 106.8 (3) |
O1—C9—C10 | 115.2 (3) | N3—C4—C7 | 121.6 (3) |
O1—C9—C8 | 124.8 (4) | C5—C4—C7 | 131.6 (4) |
C8—C9—C10 | 120.0 (4) | F1—C6—F3 | 107.3 (3) |
N1—C5—C4 | 105.1 (3) | F1—C6—F2 | 107.1 (4) |
N1—C5—C6 | 123.7 (3) | F1—C6—C5 | 112.8 (4) |
C4—C5—C6 | 131.0 (4) | F3—C6—C5 | 112.1 (3) |
C10—C11—H11 | 119.9 | F2—C6—F3 | 105.9 (4) |
C10—C11—C12 | 120.2 (4) | F2—C6—C5 | 111.2 (3) |
C12—C11—H11 | 119.9 | C14—C13—N1 | 118.3 (3) |
O3—C15—C14 | 122.8 (4) | C14—C13—C18 | 122.9 (4) |
O3—C15—C16 | 117.0 (4) | C18—C13—N1 | 118.8 (4) |
C16—C15—C14 | 120.2 (4) | C18—C17—H17 | 118.9 |
O2—C10—C9 | 115.6 (3) | C16—C17—C18 | 122.1 (4) |
O2—C10—C11 | 125.1 (4) | C16—C17—H17 | 118.9 |
| | | |
C20—O2—C10—C9 | −175.8 (4) | C10—C11—C12—C7 | −0.6 (7) |
C20—O2—C10—C11 | 2.5 (7) | C14—C15—C16—C17 | −2.1 (7) |
C19—O1—C9—C10 | −179.5 (4) | C12—C11—C10—O2 | −178.2 (4) |
C19—O1—C9—C8 | 1.7 (7) | C12—C11—C10—C9 | 0.0 (7) |
N1—C5—C4—N3 | 0.2 (4) | C12—C7—C8—C9 | −0.8 (6) |
N1—C5—C4—C7 | 179.2 (4) | C12—C7—C4—N3 | −149.1 (4) |
N1—C5—C6—F1 | 94.9 (5) | C12—C7—C4—C5 | 32.0 (7) |
N1—C5—C6—F3 | −26.4 (6) | C8—C9—C10—O2 | 178.6 (4) |
N1—C5—C6—F2 | −144.8 (4) | C8—C9—C10—C11 | 0.2 (7) |
O3—C15—C14—C13 | −178.0 (4) | C8—C7—C12—C11 | 1.0 (6) |
O3—C15—C16—C17 | 177.9 (4) | C8—C7—C4—N3 | 28.5 (6) |
N2—N1—C5—C4 | −0.1 (4) | C8—C7—C4—C5 | −150.4 (5) |
N2—N1—C5—C6 | 175.8 (4) | C16—C15—C14—C13 | 2.0 (6) |
N2—N1—C13—C14 | −48.9 (5) | C4—N3—N2—N1 | 0.3 (5) |
N2—N1—C13—C18 | 129.1 (4) | C4—C5—C6—F1 | −90.4 (5) |
N2—N3—C4—C5 | −0.3 (5) | C4—C5—C6—F3 | 148.3 (4) |
N2—N3—C4—C7 | −179.5 (4) | C4—C5—C6—F2 | 29.9 (7) |
O1—C9—C10—O2 | −0.3 (6) | C4—C7—C12—C11 | 178.6 (4) |
O1—C9—C10—C11 | −178.7 (4) | C4—C7—C8—C9 | −178.5 (4) |
O1—C9—C8—C7 | 179.0 (4) | C6—C5—C4—N3 | −175.2 (4) |
C5—N1—N2—N3 | −0.1 (4) | C6—C5—C4—C7 | 3.8 (8) |
C5—N1—C13—C14 | 132.6 (5) | C13—N1—N2—N3 | −179.0 (3) |
C5—N1—C13—C18 | −49.4 (6) | C13—N1—C5—C4 | 178.5 (4) |
C15—C14—C13—N1 | 177.1 (4) | C13—N1—C5—C6 | −5.6 (7) |
C15—C14—C13—C18 | −0.9 (7) | C13—C18—C17—C16 | 0.1 (7) |
C15—C16—C17—C18 | 1.0 (7) | C17—C18—C13—N1 | −178.1 (4) |
C10—C9—C8—C7 | 0.2 (7) | C17—C18—C13—C14 | −0.2 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N3i | 0.82 | 2.02 | 2.813 (4) | 163 |
Symmetry code: (i) −x+1, y+1/2, −z−1/2. |
Rotational disorder of the trifluoromethyl groups in compounds
1–7 topCompound | Comments | | Experimental | Close conformation |
1 | Molecule A | Disorder | -94.2 | 90 |
| | | 176.7 | 180 |
| Molecule B | No disorder | 89.9 | 90 |
2 | – | No disorder | -92.7 | 90 |
3 | – | Disorder | -177.4 | 180 |
| | | -163.6 | 180 |
4 | – | Disorder | -169.0 | 180 |
| | | 101.9 | 90 |
5 | – | Disorder | -75.0 | 90 |
| | | 7.0 | 0 |
6 | Disorder C/N | Disorder | -103.8 | 90 |
| | | 168.1 | 180 |
7 | – | No disorder | 94.8 | 90 |
N1—C5—C—F torsion angle (°) defined selecting the F atom of the
CF3 group closer to 0, 90 or 180°. |
Angles φ1, φ2 and φ3 (°)
Relative energies (kJ mol-1) of the seven minima (types 1–7)
for J147. In bold, the E/Z isomerism about the C═N
bond (Z: φ3 = 0°; E: φ3 = 180°). topGeometry/Energy | Types 1–7 minima | |
Optimized geometry (°) | Type 1: -11.5/63.9/4.8 | Type 2: -3.4/5.6/180.0 |
Relative energy (Erel) | Type 1: 49.5 | Type 2: 20.7 |
Optimized geometry (°) | Type 3: -15.0/94.6/-0.4 | Type 4: 0.9/177.5/-179.9 |
Relative energy (Erel) | Type 3: 53.2 | Type 4: 17.2 |
Optimized geometry (°) | Type 5: 165.9/93.6/178.9 | Type 6: -168.0/-169.7/5.7 |
Relative energy (Erel) | Type 5: 32.9 | Type 6: 49.0 |
Optimized geometry (°) | Type 7: 178.1/-178.6/179.8 | X-ray: 178.5/–178.7/179.9 |
Relative energy (Erel) | Type 7: 0.0 | X-ray: 0.2 |