organic compounds
1-[4-Chloro-3-(trifluoromethyl)phenyl]-4-phenyl-1H-1,2,3-triazole
aSRC for Biotechnology, Chemistry and Systems Biology, Faculty of Science and Technology, Deakin University, Vic, 3216, Australia, bQueensland Micro and Nanotechnology Centre, Griffith University, Brisbane 4111, Australia, and cInstitute for Frontier Materials, SRC for Biotechnology, Chemistry and Systems Biology, Faculty of Science and Technology, Deakin University, Vic, 3216, Australia
*Correspondence e-mail: P.Healy@griffith.edu.au
In the title compound, C15H9ClF3N3, the phenyl and chloro-trifluoromethyl benzene rings are twisted with respect to the planar triazole group, making dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the crystal, the molecules pack in a head-to-tail arrangement along the a axis with closest inter-centroid distances between the triazole rings of 3.7372 (12) Å.
Related literature
For background to the synthesis of N-aryl-1,2,3-triazoles, see: Bock et al. (2006); Irie et al. (2012). For biological background, see: Jia & Zhu (2010); Henderson et al. (2012); Alam et al. (2006, 2007). For related structures, see: Lin et al. (2008); Lin (2010).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO; program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812042705/tk5159sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042705/tk5159Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042705/tk5159Isup3.cml
Phenyl acetylene (127 mg, 1.25 mmol, 1 eq), 4-azido-1-chloro-2-(trifluoromethyl) benzene (230 mg, 1.04 mmol, 1 eq) and copper(I) chloride (10 mg, 10 mol%) were stirred in water (3 ml) for 10 min. The solution was then stirred under microwave irradiation at 100°C for 30 min in a sealed vessel. The solution cooled to room temperature, dichloromethane (3 ml) was added and the biphasic mixture stirred for 3 min. The aqueous phase was then extracted using dichloromethane (2 x 10 ml), the combined organic layers were washed with HCl (4M, 5 ml), NaOH (1M, 5 ml), water (5 ml). The organic phase dried over MgSO4, filtered and concentrated under vacuum. The solution was then taken up in chloroform and allowed to slowly evaporate. ν (max) cm-1 3124, 1495, 1310, 1147, 1037. 1H NMR (400 MHz, CDCl3): δ = 9.50 (1H, s, triazole H), 8.42 (1H, s, ArH), 8.32 (1H, dd, J = 8.7, 2.6 Hz, ArH), 8.02 (1H, d, J = 8.7 Hz, ArH), 7.95 (2H, d, J = 8 Hz, ArH), 7.51 (2H, m, ArH), 7.40 (1H, m, ArH). 13C NMR (100 MHz, CDCl3): δ = 148.22, 136.16, 133.98, 130.91 (m), 130.47, 129.65, 129.04, 128.53 (q, J2C—F = 32 Hz), 125.93, 125.70 (m), 122.89 (q, J1C—F = 272 Hz), 120.62, 119.75. M.pt: 443–445.3 K. HRMS, m/z calcd for(C15H9ClF3N3) 324.05099, found 324.05011.
The carbon-bound H atoms were constrained as riding with C—H = 0.95 Å, and with Uiso(H) = 1.2Ueq of the parent C atom.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 2001) and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).C15H9ClF3N3 | F(000) = 1312 |
Mr = 323.70 | Dx = 1.597 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -C 2yc | Cell parameters from 1854 reflections |
a = 30.7475 (16) Å | θ = 3.4–30.3° |
b = 5.8877 (3) Å | µ = 0.32 mm−1 |
c = 15.4364 (8) Å | T = 249 K |
β = 105.470 (5)° | Block, colourless |
V = 2693.2 (2) Å3 | 0.33 × 0.26 × 0.24 mm |
Z = 8 |
Oxford Diffraction GEMINI S Ultra diffractometer | 2355 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1899 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 16.0774 pixels mm-1 | θmax = 25.0°, θmin = 3.4° |
ω and ϕ scans | h = −36→33 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012), | k = −5→6 |
Tmin = 0.902, Tmax = 0.928 | l = −9→18 |
3934 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0327P)2 + 2.2063P] where P = (Fo2 + 2Fc2)/3 |
2355 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C15H9ClF3N3 | V = 2693.2 (2) Å3 |
Mr = 323.70 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 30.7475 (16) Å | µ = 0.32 mm−1 |
b = 5.8877 (3) Å | T = 249 K |
c = 15.4364 (8) Å | 0.33 × 0.26 × 0.24 mm |
β = 105.470 (5)° |
Oxford Diffraction GEMINI S Ultra diffractometer | 2355 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012), | 1899 reflections with I > 2σ(I) |
Tmin = 0.902, Tmax = 0.928 | Rint = 0.021 |
3934 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.18 e Å−3 |
2355 reflections | Δρmin = −0.22 e Å−3 |
199 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.78052 (2) | 0.33228 (12) | 0.32573 (4) | 0.0454 (2) | |
F1 | 0.76886 (4) | 0.0366 (3) | 0.48769 (11) | 0.0575 (6) | |
F2 | 0.78035 (5) | −0.1587 (3) | 0.37911 (10) | 0.0587 (5) | |
F3 | 0.81441 (4) | −0.2452 (3) | 0.51428 (10) | 0.0522 (5) | |
N1 | 0.96027 (6) | 0.1414 (3) | 0.56964 (11) | 0.0285 (6) | |
N2 | 0.97402 (6) | −0.0774 (3) | 0.58511 (13) | 0.0369 (6) | |
N3 | 1.01508 (6) | −0.0729 (3) | 0.63832 (12) | 0.0358 (6) | |
C4 | 1.02780 (7) | 0.1481 (4) | 0.65769 (13) | 0.0276 (7) | |
C5 | 0.99302 (7) | 0.2849 (4) | 0.61383 (14) | 0.0281 (7) | |
C11 | 0.91648 (7) | 0.1919 (4) | 0.51321 (13) | 0.0275 (6) | |
C12 | 0.88165 (7) | 0.0422 (4) | 0.51110 (13) | 0.0281 (7) | |
C13 | 0.83879 (7) | 0.0861 (4) | 0.45597 (13) | 0.0277 (7) | |
C14 | 0.83212 (7) | 0.2782 (4) | 0.40213 (13) | 0.0293 (7) | |
C15 | 0.86683 (7) | 0.4302 (4) | 0.40630 (14) | 0.0335 (7) | |
C16 | 0.90929 (7) | 0.3881 (4) | 0.46234 (14) | 0.0324 (7) | |
C17 | 0.80065 (7) | −0.0695 (4) | 0.45873 (15) | 0.0365 (8) | |
C41 | 1.07225 (7) | 0.2101 (4) | 0.71678 (13) | 0.0276 (7) | |
C42 | 1.10818 (7) | 0.0584 (4) | 0.73080 (14) | 0.0344 (7) | |
C43 | 1.15027 (7) | 0.1168 (5) | 0.78475 (15) | 0.0394 (8) | |
C44 | 1.15723 (8) | 0.3258 (5) | 0.82582 (15) | 0.0398 (8) | |
C45 | 1.12182 (8) | 0.4780 (5) | 0.81243 (14) | 0.0389 (8) | |
C46 | 1.07966 (7) | 0.4216 (4) | 0.75828 (14) | 0.0333 (7) | |
H5 | 0.99210 | 0.43430 | 0.61430 | 0.0340* | |
H12 | 0.88700 | −0.09090 | 0.54740 | 0.0330* | |
H15 | 0.86140 | 0.56400 | 0.37040 | 0.0400* | |
H16 | 0.93320 | 0.49300 | 0.46580 | 0.0390* | |
H42 | 1.10380 | −0.08670 | 0.70260 | 0.0410* | |
H43 | 1.17450 | 0.01160 | 0.79350 | 0.0470* | |
H44 | 1.18610 | 0.36500 | 0.86340 | 0.0480* | |
H45 | 1.12650 | 0.62270 | 0.84080 | 0.0470* | |
H46 | 1.05570 | 0.52790 | 0.74940 | 0.0400* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0334 (3) | 0.0438 (4) | 0.0481 (3) | 0.0047 (3) | −0.0079 (3) | 0.0048 (3) |
F1 | 0.0322 (7) | 0.0558 (11) | 0.0906 (11) | −0.0039 (8) | 0.0271 (8) | −0.0025 (9) |
F2 | 0.0579 (9) | 0.0458 (10) | 0.0574 (9) | −0.0175 (8) | −0.0109 (7) | −0.0089 (8) |
F3 | 0.0371 (8) | 0.0447 (10) | 0.0679 (9) | −0.0101 (7) | 0.0019 (7) | 0.0210 (8) |
N1 | 0.0223 (9) | 0.0286 (11) | 0.0336 (9) | 0.0001 (8) | 0.0055 (7) | 0.0002 (8) |
N2 | 0.0283 (10) | 0.0288 (12) | 0.0489 (11) | −0.0018 (9) | 0.0020 (9) | −0.0005 (9) |
N3 | 0.0257 (9) | 0.0317 (12) | 0.0447 (11) | 0.0000 (9) | 0.0003 (8) | 0.0003 (9) |
C4 | 0.0243 (11) | 0.0294 (13) | 0.0300 (11) | −0.0012 (10) | 0.0087 (9) | 0.0004 (10) |
C5 | 0.0246 (11) | 0.0266 (13) | 0.0331 (11) | −0.0036 (10) | 0.0077 (9) | −0.0017 (10) |
C11 | 0.0225 (10) | 0.0309 (13) | 0.0288 (10) | −0.0002 (10) | 0.0066 (9) | −0.0014 (10) |
C12 | 0.0260 (11) | 0.0294 (13) | 0.0280 (10) | 0.0024 (10) | 0.0058 (9) | 0.0011 (10) |
C13 | 0.0255 (11) | 0.0288 (13) | 0.0286 (11) | −0.0020 (10) | 0.0068 (9) | −0.0048 (9) |
C14 | 0.0264 (11) | 0.0326 (14) | 0.0276 (11) | 0.0034 (10) | 0.0051 (9) | −0.0022 (10) |
C15 | 0.0341 (12) | 0.0321 (14) | 0.0346 (12) | 0.0041 (11) | 0.0096 (10) | 0.0064 (10) |
C16 | 0.0274 (11) | 0.0332 (14) | 0.0372 (12) | −0.0039 (10) | 0.0099 (10) | 0.0015 (10) |
C17 | 0.0263 (11) | 0.0368 (15) | 0.0419 (13) | −0.0019 (11) | 0.0012 (10) | 0.0003 (12) |
C41 | 0.0262 (11) | 0.0310 (13) | 0.0259 (10) | −0.0011 (10) | 0.0075 (9) | 0.0030 (10) |
C42 | 0.0306 (11) | 0.0335 (14) | 0.0373 (12) | 0.0007 (11) | 0.0059 (10) | 0.0005 (11) |
C43 | 0.0284 (12) | 0.0453 (17) | 0.0417 (13) | 0.0045 (12) | 0.0044 (10) | 0.0083 (12) |
C44 | 0.0305 (12) | 0.0508 (17) | 0.0324 (12) | −0.0082 (13) | −0.0016 (10) | 0.0047 (12) |
C45 | 0.0422 (13) | 0.0381 (15) | 0.0323 (12) | −0.0082 (12) | 0.0026 (10) | −0.0042 (11) |
C46 | 0.0332 (12) | 0.0345 (14) | 0.0315 (11) | 0.0031 (11) | 0.0076 (10) | 0.0002 (10) |
Cl1—C14 | 1.735 (2) | C15—C16 | 1.383 (3) |
F1—C17 | 1.334 (3) | C41—C42 | 1.392 (3) |
F2—C17 | 1.329 (3) | C41—C46 | 1.391 (3) |
F3—C17 | 1.338 (3) | C42—C43 | 1.383 (3) |
N1—N2 | 1.357 (3) | C43—C44 | 1.375 (4) |
N1—C5 | 1.352 (3) | C44—C45 | 1.382 (4) |
N1—C11 | 1.426 (3) | C45—C46 | 1.383 (3) |
N2—N3 | 1.310 (3) | C5—H5 | 0.8800 |
N3—C4 | 1.369 (3) | C12—H12 | 0.9500 |
C4—C5 | 1.366 (3) | C15—H15 | 0.9500 |
C4—C41 | 1.473 (3) | C16—H16 | 0.9500 |
C11—C12 | 1.381 (3) | C42—H42 | 0.9500 |
C11—C16 | 1.381 (3) | C43—H43 | 0.9500 |
C12—C13 | 1.389 (3) | C44—H44 | 0.9500 |
C13—C14 | 1.386 (3) | C45—H45 | 0.9500 |
C13—C17 | 1.498 (3) | C46—H46 | 0.9500 |
C14—C15 | 1.381 (3) | ||
Cl1···F1 | 3.1445 (18) | C41···H15x | 3.0300 |
Cl1···F2 | 3.0063 (19) | C42···H45vi | 3.0400 |
Cl1···F2i | 3.1086 (19) | C42···H15x | 3.0100 |
Cl1···F2ii | 3.2167 (16) | C43···H15x | 2.9900 |
F1···Cl1 | 3.1445 (18) | C44···H15x | 3.0000 |
F1···F1iii | 2.835 (2) | C45···H42i | 3.0400 |
F1···F3iv | 3.075 (2) | C45···H15x | 3.0100 |
F2···Cl1v | 3.2167 (16) | C46···H5 | 3.0000 |
F2···Cl1vi | 3.1085 (19) | C46···H15x | 3.0300 |
F2···Cl1 | 3.0063 (19) | H5···N2i | 2.9400 |
F3···C45vii | 3.295 (3) | H5···C16 | 2.9800 |
F3···C15vi | 3.235 (3) | H5···C46 | 3.0000 |
F3···F1iv | 3.075 (2) | H5···H16 | 2.5400 |
F1···H44viii | 2.8100 | H5···H46 | 2.5100 |
F3···H45vii | 2.6000 | H12···F3 | 2.3400 |
F3···H12 | 2.3400 | H12···N2 | 2.5800 |
N2···H5vi | 2.9400 | H12···H45vii | 2.5300 |
N2···H12 | 2.5800 | H15···C41x | 3.0300 |
N3···H42 | 2.6400 | H15···C42x | 3.0100 |
C5···C46ix | 3.449 (3) | H15···C43x | 2.9900 |
C12···C43ix | 3.569 (3) | H15···C44x | 3.0000 |
C12···C44ix | 3.487 (3) | H15···C45x | 3.0100 |
C15···C45x | 3.527 (3) | H15···C46x | 3.0300 |
C15···C46x | 3.486 (3) | H16···C5 | 2.8000 |
C15···F3i | 3.235 (3) | H16···H5 | 2.5400 |
C43···C12ix | 3.569 (3) | H42···N3 | 2.6400 |
C44···C12ix | 3.487 (3) | H42···C45vi | 3.0400 |
C45···F3xi | 3.295 (3) | H42···C14xii | 3.0800 |
C45···C15x | 3.527 (3) | H42···C15xii | 2.9200 |
C46···C5ix | 3.449 (3) | H42···C16xii | 3.0400 |
C46···C15x | 3.486 (3) | H44···F1xiii | 2.8100 |
C5···H16 | 2.8000 | H45···C42i | 3.0400 |
C5···H46 | 2.8300 | H45···F3xi | 2.6000 |
C14···H42xii | 3.0800 | H45···H12xi | 2.5300 |
C15···H42xii | 2.9200 | H46···C5 | 2.8300 |
C16···H42xii | 3.0400 | H46···H5 | 2.5100 |
C16···H5 | 2.9800 | ||
N2—N1—C5 | 110.45 (18) | C4—C41—C42 | 120.3 (2) |
N2—N1—C11 | 120.29 (18) | C4—C41—C46 | 121.2 (2) |
C5—N1—C11 | 129.26 (19) | C42—C41—C46 | 118.5 (2) |
N1—N2—N3 | 107.10 (17) | C41—C42—C43 | 120.7 (2) |
N2—N3—C4 | 109.13 (17) | C42—C43—C44 | 120.4 (2) |
N3—C4—C5 | 108.19 (19) | C43—C44—C45 | 119.5 (2) |
N3—C4—C41 | 122.3 (2) | C44—C45—C46 | 120.6 (2) |
C5—C4—C41 | 129.5 (2) | C41—C46—C45 | 120.4 (2) |
N1—C5—C4 | 105.1 (2) | N1—C5—H5 | 127.00 |
N1—C11—C12 | 118.77 (19) | C4—C5—H5 | 127.00 |
N1—C11—C16 | 120.2 (2) | C11—C12—H12 | 120.00 |
C12—C11—C16 | 121.0 (2) | C13—C12—H12 | 120.00 |
C11—C12—C13 | 119.9 (2) | C14—C15—H15 | 120.00 |
C12—C13—C14 | 118.9 (2) | C16—C15—H15 | 120.00 |
C12—C13—C17 | 119.4 (2) | C11—C16—H16 | 120.00 |
C14—C13—C17 | 121.63 (19) | C15—C16—H16 | 120.00 |
Cl1—C14—C13 | 121.30 (17) | C41—C42—H42 | 120.00 |
Cl1—C14—C15 | 117.89 (17) | C43—C42—H42 | 120.00 |
C13—C14—C15 | 120.8 (2) | C42—C43—H43 | 120.00 |
C14—C15—C16 | 120.1 (2) | C44—C43—H43 | 120.00 |
C11—C16—C15 | 119.1 (2) | C43—C44—H44 | 120.00 |
F1—C17—F2 | 106.84 (18) | C45—C44—H44 | 120.00 |
F1—C17—F3 | 106.38 (18) | C44—C45—H45 | 120.00 |
F1—C17—C13 | 111.87 (19) | C46—C45—H45 | 120.00 |
F2—C17—F3 | 106.10 (19) | C41—C46—H46 | 120.00 |
F2—C17—C13 | 113.17 (18) | C45—C46—H46 | 120.00 |
F3—C17—C13 | 112.02 (18) | ||
C5—N1—N2—N3 | −0.2 (2) | C11—C12—C13—C17 | −176.1 (2) |
C11—N1—N2—N3 | 179.82 (18) | C12—C13—C14—C15 | −3.3 (3) |
N2—N1—C5—C4 | −0.1 (2) | C17—C13—C14—Cl1 | −7.2 (3) |
C11—N1—C5—C4 | 179.94 (19) | C12—C13—C17—F1 | 116.4 (2) |
N2—N1—C11—C12 | 32.1 (3) | C12—C13—C17—F2 | −122.9 (2) |
N2—N1—C11—C16 | −148.4 (2) | C17—C13—C14—C15 | 174.3 (2) |
C5—N1—C11—C12 | −147.9 (2) | C12—C13—C14—Cl1 | 175.22 (16) |
C5—N1—C11—C16 | 31.6 (3) | C14—C13—C17—F2 | 59.6 (3) |
N1—N2—N3—C4 | 0.4 (2) | C14—C13—C17—F3 | 179.48 (19) |
N2—N3—C4—C5 | −0.4 (2) | C12—C13—C17—F3 | −3.0 (3) |
N2—N3—C4—C41 | 179.51 (19) | C14—C13—C17—F1 | −61.2 (3) |
C41—C4—C5—N1 | −179.6 (2) | Cl1—C14—C15—C16 | −176.31 (17) |
N3—C4—C5—N1 | 0.3 (2) | C13—C14—C15—C16 | 2.2 (3) |
C5—C4—C41—C42 | −158.3 (2) | C14—C15—C16—C11 | 0.5 (3) |
C5—C4—C41—C46 | 20.4 (3) | C4—C41—C42—C43 | 178.7 (2) |
N3—C4—C41—C46 | −159.5 (2) | C42—C41—C46—C45 | −0.3 (3) |
N3—C4—C41—C42 | 21.9 (3) | C46—C41—C42—C43 | 0.0 (3) |
C16—C11—C12—C13 | 1.2 (3) | C4—C41—C46—C45 | −179.0 (2) |
N1—C11—C12—C13 | −179.29 (19) | C41—C42—C43—C44 | 0.3 (3) |
N1—C11—C16—C15 | 178.24 (19) | C42—C43—C44—C45 | −0.3 (4) |
C12—C11—C16—C15 | −2.2 (3) | C43—C44—C45—C46 | 0.0 (4) |
C11—C12—C13—C14 | 1.6 (3) | C44—C45—C46—C41 | 0.3 (3) |
Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, −y+1/2, −z+1; (iv) −x+3/2, −y−1/2, −z+1; (v) −x+3/2, y−1/2, −z+1/2; (vi) x, y−1, z; (vii) −x+2, y−1, −z+3/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) −x+2, y, −z+3/2; (x) −x+2, −y+1, −z+1; (xi) −x+2, y+1, −z+3/2; (xii) −x+2, −y, −z+1; (xiii) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H9ClF3N3 |
Mr | 323.70 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 249 |
a, b, c (Å) | 30.7475 (16), 5.8877 (3), 15.4364 (8) |
β (°) | 105.470 (5) |
V (Å3) | 2693.2 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.33 × 0.26 × 0.24 |
Data collection | |
Diffractometer | Oxford Diffraction GEMINI S Ultra diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012), |
Tmin, Tmax | 0.902, 0.928 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3934, 2355, 1899 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.091, 1.07 |
No. of reflections | 2355 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.22 |
Computer programs: CrysAlis PRO (Agilent, 2012), TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999), TEXSAN (Molecular Structure Corporation, 2001) and SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).
Acknowledgements
We acknowledge support of this work by Griffith University, the Queensland University of Technology, the Strategic Research Center for Biotechnology, Chemistry and Systems Biology and the Institute for Frontier Materials Deakin University.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The structure of the title compound, (I), was determined as part of an ongoing project developing N-aryl-1,2,3-triazoles as amide mimetics for medicinal applications. The synthesis of 1,2,3-triazoles via copper mediated 1,3-dipolar reactions has become one of the most widely used methodologies to tether molecules together or to a surface (Bock et al., 2006; Irie et al., 2012). Electronically deactivated N-phenyl-1,2,3-triazoles have been employed in several areas such as the combinatorial development of kinase inhibitors (Jia & Zhu, 2010) in the development of monoamine oxidase inhibitors, androgen receptor antagonists (Henderson et al., 2012) and as GABA receptor antagonists (Alam et al., 2006; Alam et al., 2007). This compound provides an aryl chloride moiety in the para-position relative to the triazole ring providing a synthetic handle for further structural elaboration.
In the molecular structure of (I) (Fig. 1) the planar phenyl and chloro-trifluoromethyl benzene rings are twisted with respect to the central planar triazole group with dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the triazole ring, the N1—N2 and N2—N3 bond lengths are 1.357 (3) and 1.310 (3) Å, respectively. and are similar to those reported for related compounds (Lin et al., 2008; Lin, 2010). In the crystal lattice, the molecules stack in a head to tail arrangement along the a axis (Fig. 2) with the centroid-centroid distances between the triazole rings 4.1494 (12) and 3.7372 (12) Å.