Literature DB >> 23284474

1-[4-Chloro-3-(trifluoro-meth-yl)phen-yl]-4-phenyl-1H-1,2,3-triazole.

Jarrad M Altimari1, Peter C Healy, Luke C Henderson.   

Abstract

In the title compound, C(15)H(9)ClF(3)N(3), the phenyl and chloro-trifluoro-methyl 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 mol-ecules 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.

Entities:  

Year:  2012        PMID： 23284474      PMCID： PMC3515254          DOI： 10.1107/S1600536812042705

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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

C15H9ClF3N3 M = 323.70 Monoclinic, a = 30.7475 (16) Å b = 5.8877 (3) Å c = 15.4364 (8) Å β = 105.470 (5)° V = 2693.2 (2) Å3 Z = 8 Mo Kα radiation μ = 0.32 mm−1 T = 249 K 0.33 × 0.26 × 0.24 mm

Data collection

Oxford Diffraction GEMINI S Ultra diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶), T min = 0.902, T max = 0.928 3934 measured reflections 2355 independent reflections 1899 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.091 S = 1.07 2355 reflections 199 parameters H-atom parameters constrained Δρmax = 0.18 e Å−3 Δρmin = −0.22 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042705/tk5159sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042705/tk5159Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812042705/tk5159Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H9ClF3N3F(000) = 1312
Mr = 323.70Dx = 1.597 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2ycCell parameters from 1854 reflections
a = 30.7475 (16) Åθ = 3.4–30.3°
b = 5.8877 (3) ŵ = 0.32 mm−1
c = 15.4364 (8) ÅT = 249 K
β = 105.470 (5)°Block, colourless
V = 2693.2 (2) Å30.33 × 0.26 × 0.24 mm
Z = 8
Oxford Diffraction GEMINI S Ultra diffractometer2355 independent reflections
Radiation source: Enhance (Mo) X-ray Source1899 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 16.0774 pixels mm-1θmax = 25.0°, θmin = 3.4°
ω and φ scansh = −36→33
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012),k = −5→6
Tmin = 0.902, Tmax = 0.928l = −9→18
3934 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0327P)2 + 2.2063P] where P = (Fo2 + 2Fc2)/3
2355 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
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.
xyzUiso*/Ueq
Cl10.78052 (2)0.33228 (12)0.32573 (4)0.0454 (2)
F10.76886 (4)0.0366 (3)0.48769 (11)0.0575 (6)
F20.78035 (5)−0.1587 (3)0.37911 (10)0.0587 (5)
F30.81441 (4)−0.2452 (3)0.51428 (10)0.0522 (5)
N10.96027 (6)0.1414 (3)0.56964 (11)0.0285 (6)
N20.97402 (6)−0.0774 (3)0.58511 (13)0.0369 (6)
N31.01508 (6)−0.0729 (3)0.63832 (12)0.0358 (6)
C41.02780 (7)0.1481 (4)0.65769 (13)0.0276 (7)
C50.99302 (7)0.2849 (4)0.61383 (14)0.0281 (7)
C110.91648 (7)0.1919 (4)0.51321 (13)0.0275 (6)
C120.88165 (7)0.0422 (4)0.51110 (13)0.0281 (7)
C130.83879 (7)0.0861 (4)0.45597 (13)0.0277 (7)
C140.83212 (7)0.2782 (4)0.40213 (13)0.0293 (7)
C150.86683 (7)0.4302 (4)0.40630 (14)0.0335 (7)
C160.90929 (7)0.3881 (4)0.46234 (14)0.0324 (7)
C170.80065 (7)−0.0695 (4)0.45873 (15)0.0365 (8)
C411.07225 (7)0.2101 (4)0.71678 (13)0.0276 (7)
C421.10818 (7)0.0584 (4)0.73080 (14)0.0344 (7)
C431.15027 (7)0.1168 (5)0.78475 (15)0.0394 (8)
C441.15723 (8)0.3258 (5)0.82582 (15)0.0398 (8)
C451.12182 (8)0.4780 (5)0.81243 (14)0.0389 (8)
C461.07966 (7)0.4216 (4)0.75828 (14)0.0333 (7)
H50.992100.434300.614300.0340*
H120.88700−0.090900.547400.0330*
H150.861400.564000.370400.0400*
H160.933200.493000.465800.0390*
H421.10380−0.086700.702600.0410*
H431.174500.011600.793500.0470*
H441.186100.365000.863400.0480*
H451.126500.622700.840800.0470*
H461.055700.527900.749400.0400*
U11U22U33U12U13U23
Cl10.0334 (3)0.0438 (4)0.0481 (3)0.0047 (3)−0.0079 (3)0.0048 (3)
F10.0322 (7)0.0558 (11)0.0906 (11)−0.0039 (8)0.0271 (8)−0.0025 (9)
F20.0579 (9)0.0458 (10)0.0574 (9)−0.0175 (8)−0.0109 (7)−0.0089 (8)
F30.0371 (8)0.0447 (10)0.0679 (9)−0.0101 (7)0.0019 (7)0.0210 (8)
N10.0223 (9)0.0286 (11)0.0336 (9)0.0001 (8)0.0055 (7)0.0002 (8)
N20.0283 (10)0.0288 (12)0.0489 (11)−0.0018 (9)0.0020 (9)−0.0005 (9)
N30.0257 (9)0.0317 (12)0.0447 (11)0.0000 (9)0.0003 (8)0.0003 (9)
C40.0243 (11)0.0294 (13)0.0300 (11)−0.0012 (10)0.0087 (9)0.0004 (10)
C50.0246 (11)0.0266 (13)0.0331 (11)−0.0036 (10)0.0077 (9)−0.0017 (10)
C110.0225 (10)0.0309 (13)0.0288 (10)−0.0002 (10)0.0066 (9)−0.0014 (10)
C120.0260 (11)0.0294 (13)0.0280 (10)0.0024 (10)0.0058 (9)0.0011 (10)
C130.0255 (11)0.0288 (13)0.0286 (11)−0.0020 (10)0.0068 (9)−0.0048 (9)
C140.0264 (11)0.0326 (14)0.0276 (11)0.0034 (10)0.0051 (9)−0.0022 (10)
C150.0341 (12)0.0321 (14)0.0346 (12)0.0041 (11)0.0096 (10)0.0064 (10)
C160.0274 (11)0.0332 (14)0.0372 (12)−0.0039 (10)0.0099 (10)0.0015 (10)
C170.0263 (11)0.0368 (15)0.0419 (13)−0.0019 (11)0.0012 (10)0.0003 (12)
C410.0262 (11)0.0310 (13)0.0259 (10)−0.0011 (10)0.0075 (9)0.0030 (10)
C420.0306 (11)0.0335 (14)0.0373 (12)0.0007 (11)0.0059 (10)0.0005 (11)
C430.0284 (12)0.0453 (17)0.0417 (13)0.0045 (12)0.0044 (10)0.0083 (12)
C440.0305 (12)0.0508 (17)0.0324 (12)−0.0082 (13)−0.0016 (10)0.0047 (12)
C450.0422 (13)0.0381 (15)0.0323 (12)−0.0082 (12)0.0026 (10)−0.0042 (11)
C460.0332 (12)0.0345 (14)0.0315 (11)0.0031 (11)0.0076 (10)0.0002 (10)
Cl1—C141.735 (2)C15—C161.383 (3)
F1—C171.334 (3)C41—C421.392 (3)
F2—C171.329 (3)C41—C461.391 (3)
F3—C171.338 (3)C42—C431.383 (3)
N1—N21.357 (3)C43—C441.375 (4)
N1—C51.352 (3)C44—C451.382 (4)
N1—C111.426 (3)C45—C461.383 (3)
N2—N31.310 (3)C5—H50.8800
N3—C41.369 (3)C12—H120.9500
C4—C51.366 (3)C15—H150.9500
C4—C411.473 (3)C16—H160.9500
C11—C121.381 (3)C42—H420.9500
C11—C161.381 (3)C43—H430.9500
C12—C131.389 (3)C44—H440.9500
C13—C141.386 (3)C45—H450.9500
C13—C171.498 (3)C46—H460.9500
C14—C151.381 (3)
Cl1···F13.1445 (18)C41···H15x3.0300
Cl1···F23.0063 (19)C42···H45vi3.0400
Cl1···F2i3.1086 (19)C42···H15x3.0100
Cl1···F2ii3.2167 (16)C43···H15x2.9900
F1···Cl13.1445 (18)C44···H15x3.0000
F1···F1iii2.835 (2)C45···H42i3.0400
F1···F3iv3.075 (2)C45···H15x3.0100
F2···Cl1v3.2167 (16)C46···H53.0000
F2···Cl1vi3.1085 (19)C46···H15x3.0300
F2···Cl13.0063 (19)H5···N2i2.9400
F3···C45vii3.295 (3)H5···C162.9800
F3···C15vi3.235 (3)H5···C463.0000
F3···F1iv3.075 (2)H5···H162.5400
F1···H44viii2.8100H5···H462.5100
F3···H45vii2.6000H12···F32.3400
F3···H122.3400H12···N22.5800
N2···H5vi2.9400H12···H45vii2.5300
N2···H122.5800H15···C41x3.0300
N3···H422.6400H15···C42x3.0100
C5···C46ix3.449 (3)H15···C43x2.9900
C12···C43ix3.569 (3)H15···C44x3.0000
C12···C44ix3.487 (3)H15···C45x3.0100
C15···C45x3.527 (3)H15···C46x3.0300
C15···C46x3.486 (3)H16···C52.8000
C15···F3i3.235 (3)H16···H52.5400
C43···C12ix3.569 (3)H42···N32.6400
C44···C12ix3.487 (3)H42···C45vi3.0400
C45···F3xi3.295 (3)H42···C14xii3.0800
C45···C15x3.527 (3)H42···C15xii2.9200
C46···C5ix3.449 (3)H42···C16xii3.0400
C46···C15x3.486 (3)H44···F1xiii2.8100
C5···H162.8000H45···C42i3.0400
C5···H462.8300H45···F3xi2.6000
C14···H42xii3.0800H45···H12xi2.5300
C15···H42xii2.9200H46···C52.8300
C16···H42xii3.0400H46···H52.5100
C16···H52.9800
N2—N1—C5110.45 (18)C4—C41—C42120.3 (2)
N2—N1—C11120.29 (18)C4—C41—C46121.2 (2)
C5—N1—C11129.26 (19)C42—C41—C46118.5 (2)
N1—N2—N3107.10 (17)C41—C42—C43120.7 (2)
N2—N3—C4109.13 (17)C42—C43—C44120.4 (2)
N3—C4—C5108.19 (19)C43—C44—C45119.5 (2)
N3—C4—C41122.3 (2)C44—C45—C46120.6 (2)
C5—C4—C41129.5 (2)C41—C46—C45120.4 (2)
N1—C5—C4105.1 (2)N1—C5—H5127.00
N1—C11—C12118.77 (19)C4—C5—H5127.00
N1—C11—C16120.2 (2)C11—C12—H12120.00
C12—C11—C16121.0 (2)C13—C12—H12120.00
C11—C12—C13119.9 (2)C14—C15—H15120.00
C12—C13—C14118.9 (2)C16—C15—H15120.00
C12—C13—C17119.4 (2)C11—C16—H16120.00
C14—C13—C17121.63 (19)C15—C16—H16120.00
Cl1—C14—C13121.30 (17)C41—C42—H42120.00
Cl1—C14—C15117.89 (17)C43—C42—H42120.00
C13—C14—C15120.8 (2)C42—C43—H43120.00
C14—C15—C16120.1 (2)C44—C43—H43120.00
C11—C16—C15119.1 (2)C43—C44—H44120.00
F1—C17—F2106.84 (18)C45—C44—H44120.00
F1—C17—F3106.38 (18)C44—C45—H45120.00
F1—C17—C13111.87 (19)C46—C45—H45120.00
F2—C17—F3106.10 (19)C41—C46—H46120.00
F2—C17—C13113.17 (18)C45—C46—H46120.00
F3—C17—C13112.02 (18)
C5—N1—N2—N3−0.2 (2)C11—C12—C13—C17−176.1 (2)
C11—N1—N2—N3179.82 (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—C4179.94 (19)C12—C13—C17—F1116.4 (2)
N2—N1—C11—C1232.1 (3)C12—C13—C17—F2−122.9 (2)
N2—N1—C11—C16−148.4 (2)C17—C13—C14—C15174.3 (2)
C5—N1—C11—C12−147.9 (2)C12—C13—C14—Cl1175.22 (16)
C5—N1—C11—C1631.6 (3)C14—C13—C17—F259.6 (3)
N1—N2—N3—C40.4 (2)C14—C13—C17—F3179.48 (19)
N2—N3—C4—C5−0.4 (2)C12—C13—C17—F3−3.0 (3)
N2—N3—C4—C41179.51 (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—N10.3 (2)C13—C14—C15—C162.2 (3)
C5—C4—C41—C42−158.3 (2)C14—C15—C16—C110.5 (3)
C5—C4—C41—C4620.4 (3)C4—C41—C42—C43178.7 (2)
N3—C4—C41—C46−159.5 (2)C42—C41—C46—C45−0.3 (3)
N3—C4—C41—C4221.9 (3)C46—C41—C42—C430.0 (3)
C16—C11—C12—C131.2 (3)C4—C41—C46—C45−179.0 (2)
N1—C11—C12—C13−179.29 (19)C41—C42—C43—C440.3 (3)
N1—C11—C16—C15178.24 (19)C42—C43—C44—C45−0.3 (4)
C12—C11—C16—C15−2.2 (3)C43—C44—C45—C460.0 (4)
C11—C12—C13—C141.6 (3)C44—C45—C46—C410.3 (3)
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