The structures of 1,4-diaryl-5-tri­fluoro­methyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease

Farrán, M. Á.; Bonet, M. Á.; Claramunt, R.M.; Torralba, M.C.; Alkorta, I.; Elguero, J.

doi:10.1107/S2053229618004394

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The structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease

M. Á. Farrán, M. Á. Bonet, R. M. Claramunt, M. C. Torralba, I. Alkorta and J. Elguero

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.

Keywords: J147; crystal structure; 1,2,3-triazoles; DFT calculations; molecular electrostatic potentials; Alzheimer's disease.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618004394/yp3155sup1.cif Contains datablocks 1_triazol34, 2_C18H16F3N3O_3OMe34, 3_C18H16F3N3O_4OMe34, 4_4OMe24Me, 5_C18H10F9N3O_abc13, 6_C19H18F3N3O4_ABC23, 7_C17H14F3N3O3, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004394/yp31551_triazol34sup7.hkl Contains datablock 1_triazol34
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004394/yp31552_C18H16F3N3O_3OMe34sup2.hkl Contains datablock 2_C18H16F3N3O_3OMe34
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004394/yp31553_C18H16F3N3O_4OMe34sup3.hkl Contains datablock 3_C18H16F3N3O_4OMe34
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004394/yp31554_4OMe24Mesup4.hkl Contains datablock 4_4OMe24Me
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004394/yp31555_C18H10F9N3O_abc13sup5.hkl Contains datablock 5_C18H10F9N3O_abc13
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004394/yp31556_C19H18F3N3O4_ABC23sup6.hkl Contains datablock 6_C19H18F3N3O4_ABC23
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004394/yp31557_C17H14F3N3O3sup8.hkl Contains datablock 7_C17H14F3N3O3
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618004394/yp31551_triazol34sup9.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618004394/yp31552_C18H16F3N3O_3OMe34sup10.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618004394/yp31553_C18H16F3N3O_4OMe34sup11.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618004394/yp31554_4OMe24Mesup12.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618004394/yp31555_C18H10F9N3O_abc13sup13.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618004394/yp31556_C19H18F3N3O4_ABC23sup14.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618004394/yp31557_C17H14F3N3O3sup15.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618004394/yp3155sup16.pdf NMR spectra and theoretical calculations

CCDC references: 1590422; 1590421; 1826637; 1590419; 1590418; 1590417; 1590416

Computing details top

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-1H-1,2,3-triazole (1_triazol34) top

Crystal data top

C₁₇H₁₄F₃N₃	F(000) = 1312
M_r = 317.31	D_x = 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	R_int = 0.045
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	θ_max = 25.0°, θ_min = 2.3°
T_min = 0.859, T_max = 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(F_o²) + (0.037P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5504 reflections	Δρ_max = 0.15 e Å⁻³
447 parameters	Δρ_min = −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	U_iso*/U_eq	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-1H-1,2,3-triazole (2_C18H16F3N3O_3OMe34) top

Crystal data top

C₁₈H₁₆F₃N₃O	D_x = 1.353 Mg m⁻³
M_r = 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	R_int = 0.070
phi and ω scans	θ_max = 25.0°, θ_min = 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(F_o²) + (0.0523P)² + 0.6011P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3001 reflections	Δρ_max = 0.13 e Å⁻³
226 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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-1H-1,2,3-triazole (3_C18H16F3N3O_4OMe34) top

Crystal data top

C₁₈H₁₆F₃N₃O	F(000) = 720
M_r = 347.34	D_x = 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	R_int = 0.045
Graphite monochromator	θ_max = 25.0°, θ_min = 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(F_o²) + (0.053P)² + 0.0053P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2930 reflections	Δρ_max = 0.15 e Å⁻³
254 parameters	Δρ_min = −0.13 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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-1H-1,2,3-triazole (4_4OMe24Me) top

Crystal data top

C₁₈H₁₆F₃N₃O	Z = 2
M_r = 347.34	F(000) = 360
Triclinic, P1	D_x = 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	R_int = 0.092
phi and ω scans	θ_max = 25.5°, θ_min = 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(F_o²) + (0.0648P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3096 reflections	Δρ_max = 0.23 e Å⁻³
254 parameters	Δρ_min = −0.14 e Å⁻³
292 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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-1H-1,2,3-triazole (5_C18H10F9N3O_abc13) top

Crystal data top

C₁₈H₁₀F₉N₃O	F(000) = 912
M_r = 455.29	D_x = 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	R_int = 0.040
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.051P)² + 0.098P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3688 reflections	Δρ_max = 0.13 e Å⁻³
365 parameters	Δρ_min = −0.17 e Å⁻³
484 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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-1H-1,2,3-triazole (6_C19H18F3N3O4_ABC23) top

Crystal data top

C₁₉H₁₈F₃N₃O₄	F(000) = 848
M_r = 409.36	D_x = 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	R_int = 0.049
phi and ω scans	θ_max = 25.5°, θ_min = 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(F_o²) + (0.0587P)² + 0.1371P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3634 reflections	Δρ_max = 0.14 e Å⁻³
289 parameters	Δρ_min = −0.13 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)-1H-1,2,3-triazol-1-yl]phenol (7_C17H14F3N3O3) top

Crystal data top

C₁₇H₁₄F₃N₃O₃	F(000) = 752
M_r = 365.31	D_x = 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	R_int = 0.146
phi and ω scans	θ_max = 26.0°, θ_min = 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(F_o²) + (0.0845P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3188 reflections	Δρ_max = 0.26 e Å⁻³
235 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 top

Compound	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°). top

Geometry/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 (E_rel)	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 (E_rel)	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 (E_rel)	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 (E_rel)	Type 7: 0.0	X-ray: 0.2

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The structures of 1,4-diaryl-5-tri­fluoro­methyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease

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The structures of 1,4-diaryl-5-trifluoromethyl-1H-1,2,3-triazoles related to J147, a drug for treating Alzheimer's disease