Literature DB >> 26396783

Crystal structure of 1-(4-fluoro-phen-yl)-4-(4-meth-oxy-phen-yl)-1H-1,2,3-triazole.

Balbir Kumar1, Madhvi Bhardwaj2, Satya Paul2, Rajni Kant1, Vivek K Gupta1.   

Abstract

In the title compound, C15H12FN3O, the triazole ring forms dihedral angles of 30.57 (8) and 21.81 (9)° with the fluoro-substituted and meth-oxy-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 51.53 (7)°. In the crystal, π-π inter-actions between the triazole rings [centroid-centroid seperations = 3.774 (2) and 3.841 (2) Å] form chains along [010].

Entities:  

Keywords:  1,2,3-triazole; crystal structure; π–π inter­actions

Year:  2015        PMID： 26396783      PMCID： PMC4571383          DOI： 10.1107/S2056989015012153

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For related literature on 1,2,3-triazoles, see: Aher et al. (2009 ▸); Jordao et al. (2009 ▸); Vijaya Raghava Reddy et al. (2010 ▸); Soltis et al. (1996 ▸). For applications of 1,2,3-triazoles, see: Pérez-Balderas et al. (2003 ▸); Wu et al. (2004 ▸); Kumar & Pandey (2008 ▸); Haridas et al. (2008 ▸); Turner et al., (2007 ▸); Angell & Burgess (2007 ▸); For the synthesis of 1,2,3-triazoles, see: Huisgen et al. (1965 ▸); Wang et al. (2010 ▸). For related structures, see: Abdel-Wahab et al. (2012 ▸); Zhang et al. (2004 ▸).

Experimental

Crystal data

C15H12FN3O M = 269.28 Triclinic, a = 5.6572 (5) Å b = 7.3692 (8) Å c = 15.5711 (15) Å α = 79.202 (9)° β = 81.159 (8)° γ = 89.442 (8)° V = 629.95 (11) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 293 K 0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▸) T min = 0.806, T max = 1.000 4369 measured reflections 2461 independent reflections 1575 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.179 S = 1.04 2461 reflections 182 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015012153/lh5772sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012153/lh5772Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015012153/lh5772Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015012153/lh5772fig1.tif The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Click here for additional data file. a . DOI: 10.1107/S2056989015012153/lh5772fig2.tif The packing arrangement of mol­ecules viewed along the a axis. CCDC reference: 1408544 Additional supporting information: crystallographic information; 3D view; checkCIF report
C15H12FN3OZ = 2
Mr = 269.28F(000) = 280
Triclinic, P1Dx = 1.420 Mg m−3Dm = 1.42 Mg m−3Dm measured by not measured
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.6572 (5) ÅCell parameters from 1205 reflections
b = 7.3692 (8) Åθ = 4.0–28.0°
c = 15.5711 (15) ŵ = 0.10 mm−1
α = 79.202 (9)°T = 293 K
β = 81.159 (8)°Block, white
γ = 89.442 (8)°0.30 × 0.20 × 0.20 mm
V = 629.95 (11) Å3
Oxford Diffraction Xcalibur Sapphire3 diffractometer2461 independent reflections
Radiation source: fine-focus sealed tube1575 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.7°
ω scansh = −4→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −7→9
Tmin = 0.806, Tmax = 1.000l = −18→19
4369 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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0744P)2 + 0.0652P] where P = (Fo2 + 2Fc2)/3
2461 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
F10.2052 (4)−0.1487 (2)0.41281 (12)0.0782 (6)
N10.1232 (4)0.1852 (3)0.07275 (13)0.0404 (5)
N2−0.0970 (4)0.1982 (3)0.04842 (15)0.0505 (6)
N3−0.0714 (4)0.2743 (3)−0.03467 (15)0.0489 (6)
C40.1657 (4)0.3132 (3)−0.06593 (16)0.0367 (6)
C50.2893 (4)0.2552 (3)0.00235 (15)0.0395 (6)
H50.45400.26230.00090.047*
C60.2436 (4)0.3971 (3)−0.15737 (16)0.0371 (6)
C70.1015 (5)0.3849 (3)−0.22101 (17)0.0426 (6)
H7−0.04540.3228−0.20400.051*
C80.1707 (5)0.4613 (4)−0.30769 (18)0.0483 (7)
H80.07170.4501−0.34900.058*
C90.3880 (5)0.5558 (3)−0.33479 (17)0.0457 (7)
O90.4360 (4)0.6328 (3)−0.42195 (14)0.0718 (7)
C100.5341 (5)0.5698 (3)−0.27319 (17)0.0452 (6)
H100.68040.6327−0.29060.054*
C110.4626 (5)0.4900 (3)−0.18530 (16)0.0414 (6)
H110.56290.4987−0.14410.050*
C120.1484 (4)0.1035 (3)0.16056 (16)0.0371 (6)
C13−0.0340 (5)0.1177 (3)0.22842 (16)0.0430 (6)
H13−0.16940.18440.21660.052*
C14−0.0162 (5)0.0338 (4)0.31322 (18)0.0518 (7)
H14−0.13910.04170.35940.062*
C150.1878 (5)−0.0630 (3)0.32897 (18)0.0500 (7)
C160.3719 (5)−0.0751 (3)0.26282 (19)0.0503 (7)
H160.5088−0.13920.27520.060*
C170.3531 (5)0.0081 (3)0.17797 (17)0.0425 (6)
H170.47730.00070.13220.051*
C180.6617 (8)0.6997 (5)−0.4596 (2)0.0918 (12)
H18A0.70310.7988−0.43210.138*
H18B0.66480.7446−0.52180.138*
H18C0.77490.6025−0.45120.138*
U11U22U33U12U13U23
F10.0830 (15)0.0859 (12)0.0607 (12)0.0042 (11)−0.0198 (10)0.0062 (9)
N10.0268 (11)0.0459 (12)0.0481 (13)0.0005 (9)−0.0039 (9)−0.0096 (9)
N20.0252 (11)0.0691 (14)0.0558 (15)−0.0006 (10)−0.0048 (10)−0.0098 (11)
N30.0260 (12)0.0675 (15)0.0508 (14)−0.0006 (11)−0.0033 (10)−0.0069 (11)
C40.0268 (13)0.0389 (12)0.0455 (15)0.0003 (10)−0.0056 (10)−0.0105 (10)
C50.0224 (12)0.0470 (14)0.0483 (15)−0.0018 (11)−0.0025 (10)−0.0090 (11)
C60.0279 (13)0.0391 (12)0.0458 (15)0.0054 (10)−0.0075 (11)−0.0108 (10)
C70.0303 (13)0.0450 (13)0.0536 (16)−0.0001 (11)−0.0086 (11)−0.0107 (11)
C80.0393 (15)0.0583 (16)0.0513 (17)0.0049 (13)−0.0158 (13)−0.0136 (12)
C90.0450 (16)0.0499 (14)0.0404 (15)0.0101 (13)−0.0063 (12)−0.0049 (11)
O90.0608 (14)0.0911 (15)0.0542 (13)−0.0043 (12)−0.0021 (11)0.0045 (11)
C100.0321 (14)0.0458 (14)0.0553 (17)−0.0029 (12)0.0001 (12)−0.0083 (12)
C110.0331 (14)0.0447 (13)0.0484 (15)0.0003 (11)−0.0088 (11)−0.0120 (11)
C120.0293 (13)0.0358 (12)0.0458 (15)−0.0034 (10)−0.0048 (11)−0.0070 (10)
C130.0316 (13)0.0452 (14)0.0497 (16)0.0032 (11)−0.0020 (11)−0.0063 (11)
C140.0441 (16)0.0556 (16)0.0522 (18)0.0000 (14)0.0027 (13)−0.0092 (12)
C150.0532 (18)0.0471 (15)0.0493 (17)−0.0049 (13)−0.0165 (14)−0.0011 (12)
C160.0401 (15)0.0457 (14)0.0657 (19)0.0059 (12)−0.0131 (14)−0.0079 (13)
C170.0317 (13)0.0425 (13)0.0535 (16)0.0001 (11)−0.0038 (11)−0.0121 (11)
C180.091 (3)0.109 (3)0.068 (2)−0.032 (2)0.000 (2)−0.0060 (19)
F1—C151.357 (3)O9—C181.376 (4)
N1—C51.354 (3)C10—C111.384 (3)
N1—N21.354 (3)C10—H100.9300
N1—C121.415 (3)C11—H110.9300
N2—N31.297 (3)C12—C131.377 (3)
N3—C41.368 (3)C12—C171.385 (3)
C4—C51.362 (3)C13—C141.367 (3)
C4—C61.444 (3)C13—H130.9300
C5—H50.9300C14—C151.381 (4)
C6—C71.384 (3)C14—H140.9300
C6—C111.390 (3)C15—C161.363 (4)
C7—C81.360 (3)C16—C171.368 (3)
C7—H70.9300C16—H160.9300
C8—C91.387 (4)C17—H170.9300
C8—H80.9300C18—H18A0.9600
C9—O91.356 (3)C18—H18B0.9600
C9—C101.377 (4)C18—H18C0.9600
C5—N1—N2109.5 (2)C10—C11—C6121.3 (2)
C5—N1—C12130.8 (2)C10—C11—H11119.4
N2—N1—C12119.7 (2)C6—C11—H11119.4
N3—N2—N1107.7 (2)C13—C12—C17120.3 (2)
N2—N3—C4109.6 (2)C13—C12—N1119.3 (2)
C5—C4—N3107.4 (2)C17—C12—N1120.4 (2)
C5—C4—C6131.8 (2)C14—C13—C12120.1 (2)
N3—C4—C6120.8 (2)C14—C13—H13120.0
N1—C5—C4105.8 (2)C12—C13—H13120.0
N1—C5—H5127.1C13—C14—C15118.7 (2)
C4—C5—H5127.1C13—C14—H14120.7
C7—C6—C11117.5 (2)C15—C14—H14120.7
C7—C6—C4120.5 (2)F1—C15—C16119.1 (2)
C11—C6—C4122.0 (2)F1—C15—C14119.0 (3)
C8—C7—C6121.9 (3)C16—C15—C14121.9 (3)
C8—C7—H7119.1C15—C16—C17119.2 (2)
C6—C7—H7119.1C15—C16—H16120.4
C7—C8—C9120.3 (2)C17—C16—H16120.4
C7—C8—H8119.9C16—C17—C12119.7 (2)
C9—C8—H8119.9C16—C17—H17120.1
O9—C9—C10125.0 (3)C12—C17—H17120.1
O9—C9—C8115.6 (3)O9—C18—H18A109.5
C10—C9—C8119.3 (2)O9—C18—H18B109.5
C9—O9—C18120.7 (3)H18A—C18—H18B109.5
C9—C10—C11119.8 (3)O9—C18—H18C109.5
C9—C10—H10120.1H18A—C18—H18C109.5
C11—C10—H10120.1H18B—C18—H18C109.5
C5—N1—N2—N3−0.1 (3)O9—C9—C10—C11178.0 (2)
C12—N1—N2—N3−178.86 (19)C8—C9—C10—C11−0.1 (4)
N1—N2—N3—C4−0.3 (3)C9—C10—C11—C6−0.7 (4)
N2—N3—C4—C50.6 (3)C7—C6—C11—C101.0 (3)
N2—N3—C4—C6179.3 (2)C4—C6—C11—C10−179.9 (2)
N2—N1—C5—C40.5 (2)C5—N1—C12—C13150.9 (2)
C12—N1—C5—C4179.1 (2)N2—N1—C12—C13−30.7 (3)
N3—C4—C5—N1−0.7 (2)C5—N1—C12—C17−30.0 (3)
C6—C4—C5—N1−179.1 (2)N2—N1—C12—C17148.5 (2)
C5—C4—C6—C7156.9 (2)C17—C12—C13—C14−1.6 (4)
N3—C4—C6—C7−21.4 (3)N1—C12—C13—C14177.6 (2)
C5—C4—C6—C11−22.2 (4)C12—C13—C14—C150.6 (4)
N3—C4—C6—C11159.5 (2)C13—C14—C15—F1−179.1 (2)
C11—C6—C7—C8−0.4 (3)C13—C14—C15—C160.8 (4)
C4—C6—C7—C8−179.5 (2)F1—C15—C16—C17178.8 (2)
C6—C7—C8—C9−0.4 (4)C14—C15—C16—C17−1.2 (4)
C7—C8—C9—O9−177.6 (2)C15—C16—C17—C120.1 (4)
C7—C8—C9—C100.7 (4)C13—C12—C17—C161.2 (4)
C10—C9—O9—C1814.0 (4)N1—C12—C17—C16−177.9 (2)
C8—C9—O9—C18−167.9 (3)
  12 in total

1.  Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(i)-catalyzed ligation of azides and alkynes.

Authors:  Peng Wu; Alina K Feldman; Anne K Nugent; Craig J Hawker; Arnulf Scheel; Brigitte Voit; Jeffrey Pyun; Jean M J Fréchet; K Barry Sharpless; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

2.  Anion recognition by 1,2,3-triazolium receptors: application of click chemistry in anion recognition.

Authors:  Anjul Kumar; Pramod S Pandey
Journal:  Org Lett       Date:  2007-12-15       Impact factor: 6.005

3.  Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides.

Authors:  Rushia A Turner; Allen G Oliver; R Scott Lokey
Journal:  Org Lett       Date:  2007-10-23       Impact factor: 6.005

4.  Design, synthesis, and self-assembling properties of novel triazolophanes.

Authors:  V Haridas; Kashmiri Lal; Yogesh K Sharma; Shailesh Upreti
Journal:  Org Lett       Date:  2008-03-22       Impact factor: 6.005

5.  Synthesis, antiplatelet and in silico evaluations of novel N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides.

Authors:  Alessandro K Jordão; Vitor F Ferreira; Emerson S Lima; Maria C B V de Souza; Eduardo C L Carlos; Helena C Castro; Reinaldo B Geraldo; Carlos R Rodrigues; Maria C B Almeida; Anna C Cunha
Journal:  Bioorg Med Chem       Date:  2009-04-01       Impact factor: 3.641

6.  Synthesis and biological evaluation of glycal-derived novel tetrahydrofuran 1,2,3-triazoles by 'click' chemistry.

Authors:  L Vijaya Raghava Reddy; P Venkat Reddy; Nripendra N Mishra; Praveen K Shukla; Garima Yadav; Ranjana Srivastava; Arun K Shaw
Journal:  Carbohydr Res       Date:  2010-03-30       Impact factor: 2.104

7.  Identification and characterization of human metabolites of CAI [5-amino-1-1(4'-chlorobenzoyl-3,5-dichlorobenzyl)-1,2,3-triazole- 4-carboxamide).

Authors:  M J Soltis; H J Yeh; K A Cole; N Whittaker; R P Wersto; E C Kohn
Journal:  Drug Metab Dispos       Date:  1996-07       Impact factor: 3.922

8.  Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues.

Authors:  Nilkanth G Aher; Vandana S Pore; Nripendra N Mishra; Awanit Kumar; Praveen K Shukla; Aanchal Sharma; Manoj K Bhat
Journal:  Bioorg Med Chem Lett       Date:  2008-12-10       Impact factor: 2.823

9.  4-{1-[4-(4-Bromo-phen-yl)-1,3-thia-zol-2-yl]-5-(4-fluoro-phen-yl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazole.

Authors:  Bakr F Abdel-Wahab; Hanan A Mohamed; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-31

10.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.