organic compounds
1-(2′-Ethoxy-4′-fluoro-[1,1′-biphenyl]-4-yl)-4-phenyl-1H-1,2,3-triazole
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: rangappaks@chemistry.uni-mysore.ac.in
In the title compound, C22H18FN3O, the triazole ring is planar. The plane of the triazole ring makes dihedral angles of 19.31 (10), 20.52 (10) and 39.82 (9)° with the planes of the benzene rings, indicating the overall nonplanarity of the molecule. No classical hydrogen bonds were observed in the structure.
Keywords: crystal structure; 1H-1,2,3-triazole.
CCDC reference: 1511398
Structure description
Nitrogen-containing et al., 2013), antitubercular activity (Somu et al., 2006), anti-HIV activity, antibacterial activity, antiallergic activity and selective β3-adrenergic receptor agonism (Brockunier et al., 2000). They also have a wide range of other applications, such as dyes, corrosion inhibition, photostabilizers, photographic materials, and in the field of agrochemicals. Owing to their wide range of biological and technical interest and as a part of our ongoing research on triazoles (Ashwini et al., 2016), the title compound was synthesized from the 1,3-dipolar cycloaddition of an azide an and alkyne in the presence of a copper(I) catalyst to form a 1,4-disubstituted triazoles, contributing to the popularization of `click' chemistry as a highly effective method for the functionalization of triazoles.
such as 1,2,3-triazoles, have a wide-ranging biological spectrum, including anticancer activity (DuanIn the title compound (Fig. 1), the triazole ring is planar, with atom N1 deviating by 0.004 (1) Å from the mean plane. The plane of the triazole ring makes dihedral angles of 19.31 (10), 20.52 (10) and 39.82 (9)°, respectively, with the planes of the C3–C8, C9–C14 and C15–C20 benzene rings, indicating the non-planarity of the molecule as a whole. The ethoxy group lies in the plane of the fluorophenyl ring and is in an antiperiplanar conformation, as indicated by the torsion angle of −175.08 (16)°. No classical hydrogen bonds were observed in the structure.
Synthesis and crystallization
1-(4-Bromophenyl)-4-phenyl-1,2,3-triazole (1 mmol), 2-ethoxy-4-fluorobenzenboronic acid (1.2 mmol) and K2CO3 (3 mmol) were added to a mixture of ethanol, water and 1,4-dioxane in the ratio of 1:1:5 and taken into a pressure tube. The reaction mixture was stirred for 15 min in the presence of nitrogen gas to create inert atmosphere. Then Dikis, i.e. [PdCl2(PPh3)2], was added as a catalyst (0.1 mmol) to the reaction mass. The reaction mass was heated between 393 to 403 K for 30 min in a sealed tube and the progress of the reaction was monitored by The resultant mixture was filtered through a Celite bed and the filtrate concentrated under reduced pressure to remove the ethanol using a roto-evaporator. The reaction mass was extracted with ethyl acetate followed by a brine wash and dried over anhydrous sodium sulfate. The organic layer was evaporated under reduced pressure to get a crude product which was purified by using 60:120 silica gel and EtOAc–hexane as a to get the desired triazole as a white solid. Single crystals suitable for X-ray diffraction studies were obtained by the slow evaporation method by using ethanol as the solvent.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1511398
https://doi.org/10.1107/S2414314616017120/hg4017sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017120/hg4017Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616017120/hg4017Isup3.cml
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).C22H18FN3O | F(000) = 752 |
Mr = 359.39 | Dx = 1.358 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 2093 reflections |
a = 24.392 (3) Å | θ = 7.2–64.5° |
b = 5.9336 (8) Å | µ = 0.75 mm−1 |
c = 12.3651 (16) Å | T = 296 K |
β = 100.828 (8)° | Rectangle, white |
V = 1757.8 (4) Å3 | 0.30 × 0.27 × 0.26 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 2882 independent reflections |
Radiation source: Rotating Anode | 2093 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.5°, θmin = 7.2° |
φ and ω scans | h = −28→24 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −6→6 |
Tmin = 0.805, Tmax = 0.828 | l = −14→14 |
12946 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0787P)2 + 0.0093P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2882 reflections | Δρmax = 0.23 e Å−3 |
246 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (4) |
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 esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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 | ||
F1 | 0.05300 (5) | 0.8669 (2) | −0.28028 (9) | 0.0837 (5) | |
O1 | 0.11703 (5) | 0.4164 (2) | 0.03622 (10) | 0.0574 (5) | |
N1 | 0.31578 (6) | 0.5776 (2) | 0.40783 (12) | 0.0492 (5) | |
N2 | 0.32422 (7) | 0.3614 (3) | 0.44199 (15) | 0.0703 (7) | |
N3 | 0.35374 (8) | 0.3674 (3) | 0.54193 (15) | 0.0696 (7) | |
C1 | 0.33979 (7) | 0.7201 (3) | 0.48777 (14) | 0.0498 (7) | |
C2 | 0.36432 (7) | 0.5852 (3) | 0.57278 (15) | 0.0487 (7) | |
C3 | 0.39749 (7) | 0.6463 (3) | 0.68042 (15) | 0.0491 (7) | |
C4 | 0.42250 (8) | 0.8577 (3) | 0.69861 (16) | 0.0575 (7) | |
C5 | 0.45458 (9) | 0.9110 (4) | 0.79905 (17) | 0.0654 (8) | |
C6 | 0.46224 (9) | 0.7563 (4) | 0.88317 (17) | 0.0699 (9) | |
C7 | 0.43748 (9) | 0.5467 (4) | 0.86671 (16) | 0.0668 (8) | |
C8 | 0.40571 (8) | 0.4912 (4) | 0.76674 (15) | 0.0574 (7) | |
C9 | 0.28234 (7) | 0.6239 (3) | 0.30256 (15) | 0.0460 (6) | |
C10 | 0.27337 (8) | 0.4560 (3) | 0.22393 (16) | 0.0543 (7) | |
C11 | 0.23700 (8) | 0.4932 (3) | 0.12618 (15) | 0.0538 (7) | |
C12 | 0.20939 (7) | 0.6977 (3) | 0.10390 (14) | 0.0460 (6) | |
C13 | 0.22149 (8) | 0.8679 (3) | 0.18198 (15) | 0.0514 (7) | |
C14 | 0.25738 (8) | 0.8324 (3) | 0.28107 (16) | 0.0519 (7) | |
C15 | 0.16868 (7) | 0.7360 (3) | −0.00005 (14) | 0.0467 (7) | |
C16 | 0.12240 (8) | 0.5936 (3) | −0.03169 (14) | 0.0477 (7) | |
C17 | 0.08372 (8) | 0.6410 (3) | −0.12668 (15) | 0.0551 (7) | |
C18 | 0.09231 (9) | 0.8241 (4) | −0.18843 (15) | 0.0583 (7) | |
C19 | 0.13686 (9) | 0.9642 (4) | −0.16214 (16) | 0.0619 (8) | |
C20 | 0.17441 (8) | 0.9187 (3) | −0.06678 (15) | 0.0545 (7) | |
C21 | 0.06654 (8) | 0.2878 (3) | 0.01397 (16) | 0.0559 (7) | |
C22 | 0.06763 (9) | 0.1172 (4) | 0.10339 (17) | 0.0650 (8) | |
H1 | 0.33970 | 0.87680 | 0.48550 | 0.0600* | |
H4 | 0.41740 | 0.96370 | 0.64220 | 0.0690* | |
H5 | 0.47120 | 1.05240 | 0.81010 | 0.0780* | |
H6 | 0.48400 | 0.79250 | 0.95100 | 0.0840* | |
H7 | 0.44240 | 0.44250 | 0.92390 | 0.0800* | |
H8 | 0.38950 | 0.34910 | 0.75630 | 0.0690* | |
H10 | 0.29180 | 0.31860 | 0.23690 | 0.0650* | |
H11 | 0.23080 | 0.37900 | 0.07380 | 0.0650* | |
H13 | 0.20510 | 1.00880 | 0.16720 | 0.0620* | |
H14 | 0.26470 | 0.94760 | 0.33280 | 0.0620* | |
H17 | 0.05250 | 0.54980 | −0.14780 | 0.0660* | |
H19 | 0.14180 | 1.08580 | −0.20670 | 0.0740* | |
H20 | 0.20480 | 1.01430 | −0.04640 | 0.0650* | |
H21A | 0.06330 | 0.21250 | −0.05660 | 0.0670* | |
H21B | 0.03460 | 0.38660 | 0.01090 | 0.0670* | |
H22A | 0.10050 | 0.02550 | 0.10880 | 0.0980* | |
H22B | 0.03500 | 0.02350 | 0.08660 | 0.0980* | |
H22C | 0.06810 | 0.19290 | 0.17210 | 0.0980* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0920 (10) | 0.0886 (10) | 0.0600 (8) | 0.0091 (7) | −0.0124 (7) | 0.0138 (6) |
O1 | 0.0568 (9) | 0.0542 (9) | 0.0559 (8) | −0.0108 (6) | −0.0027 (6) | 0.0035 (6) |
N1 | 0.0496 (9) | 0.0376 (9) | 0.0565 (9) | −0.0019 (7) | −0.0003 (7) | 0.0027 (7) |
N2 | 0.0877 (13) | 0.0413 (11) | 0.0711 (12) | 0.0010 (9) | −0.0126 (10) | 0.0049 (8) |
N3 | 0.0853 (13) | 0.0454 (12) | 0.0675 (11) | 0.0005 (9) | −0.0126 (10) | 0.0052 (8) |
C1 | 0.0464 (11) | 0.0408 (12) | 0.0590 (11) | −0.0039 (8) | 0.0018 (9) | 0.0015 (9) |
C2 | 0.0451 (11) | 0.0430 (12) | 0.0566 (11) | 0.0010 (8) | 0.0058 (9) | 0.0049 (9) |
C3 | 0.0433 (11) | 0.0487 (12) | 0.0536 (11) | 0.0057 (9) | 0.0046 (9) | 0.0036 (9) |
C4 | 0.0575 (12) | 0.0529 (14) | 0.0580 (12) | 0.0006 (9) | 0.0004 (10) | 0.0045 (9) |
C5 | 0.0657 (14) | 0.0556 (14) | 0.0690 (14) | 0.0025 (10) | −0.0023 (11) | −0.0058 (11) |
C6 | 0.0723 (15) | 0.0705 (17) | 0.0603 (13) | 0.0116 (12) | −0.0045 (11) | −0.0079 (11) |
C7 | 0.0704 (14) | 0.0714 (17) | 0.0561 (12) | 0.0140 (12) | 0.0052 (11) | 0.0100 (11) |
C8 | 0.0569 (13) | 0.0531 (13) | 0.0606 (12) | 0.0046 (9) | 0.0067 (10) | 0.0064 (10) |
C9 | 0.0425 (10) | 0.0415 (11) | 0.0516 (10) | −0.0029 (8) | 0.0026 (8) | 0.0026 (8) |
C10 | 0.0547 (12) | 0.0430 (12) | 0.0627 (12) | 0.0061 (9) | 0.0043 (10) | −0.0028 (9) |
C11 | 0.0561 (12) | 0.0451 (12) | 0.0579 (11) | −0.0005 (9) | 0.0050 (10) | −0.0087 (9) |
C12 | 0.0470 (11) | 0.0407 (11) | 0.0501 (10) | −0.0034 (8) | 0.0088 (8) | −0.0010 (8) |
C13 | 0.0567 (12) | 0.0373 (11) | 0.0572 (11) | 0.0011 (8) | 0.0028 (9) | 0.0025 (8) |
C14 | 0.0557 (12) | 0.0418 (12) | 0.0541 (11) | −0.0035 (9) | −0.0002 (9) | −0.0041 (9) |
C15 | 0.0522 (12) | 0.0433 (12) | 0.0445 (10) | 0.0011 (8) | 0.0088 (8) | −0.0045 (8) |
C16 | 0.0554 (12) | 0.0430 (12) | 0.0432 (10) | 0.0023 (9) | 0.0056 (9) | −0.0031 (8) |
C17 | 0.0572 (12) | 0.0554 (13) | 0.0497 (11) | 0.0016 (10) | 0.0026 (9) | −0.0073 (9) |
C18 | 0.0662 (14) | 0.0624 (14) | 0.0425 (10) | 0.0133 (11) | 0.0003 (10) | 0.0013 (9) |
C19 | 0.0777 (15) | 0.0546 (14) | 0.0539 (12) | 0.0080 (11) | 0.0140 (11) | 0.0102 (10) |
C20 | 0.0584 (13) | 0.0490 (13) | 0.0572 (11) | −0.0002 (9) | 0.0134 (10) | −0.0005 (9) |
C21 | 0.0475 (12) | 0.0567 (13) | 0.0612 (12) | −0.0070 (9) | 0.0042 (9) | −0.0070 (10) |
C22 | 0.0634 (13) | 0.0575 (15) | 0.0721 (14) | −0.0083 (10) | 0.0074 (11) | 0.0008 (10) |
F1—C18 | 1.366 (2) | C15—C20 | 1.385 (3) |
O1—C16 | 1.367 (2) | C16—C17 | 1.390 (3) |
O1—C21 | 1.431 (2) | C17—C18 | 1.367 (3) |
N1—N2 | 1.354 (2) | C18—C19 | 1.358 (3) |
N1—C1 | 1.348 (2) | C19—C20 | 1.377 (3) |
N1—C9 | 1.427 (2) | C21—C22 | 1.496 (3) |
N2—N3 | 1.309 (3) | C1—H1 | 0.9300 |
N3—C2 | 1.358 (3) | C4—H4 | 0.9300 |
C1—C2 | 1.367 (3) | C5—H5 | 0.9300 |
C2—C3 | 1.467 (3) | C6—H6 | 0.9300 |
C3—C4 | 1.395 (3) | C7—H7 | 0.9300 |
C3—C8 | 1.395 (3) | C8—H8 | 0.9300 |
C4—C5 | 1.375 (3) | C10—H10 | 0.9300 |
C5—C6 | 1.374 (3) | C11—H11 | 0.9300 |
C6—C7 | 1.381 (3) | C13—H13 | 0.9300 |
C7—C8 | 1.370 (3) | C14—H14 | 0.9300 |
C9—C10 | 1.381 (3) | C17—H17 | 0.9300 |
C9—C14 | 1.382 (3) | C19—H19 | 0.9300 |
C10—C11 | 1.376 (3) | C20—H20 | 0.9300 |
C11—C12 | 1.390 (3) | C21—H21A | 0.9700 |
C12—C13 | 1.390 (3) | C21—H21B | 0.9700 |
C12—C15 | 1.487 (2) | C22—H22A | 0.9600 |
C13—C14 | 1.382 (3) | C22—H22B | 0.9600 |
C15—C16 | 1.406 (3) | C22—H22C | 0.9600 |
C16—O1—C21 | 118.06 (14) | C15—C20—C19 | 122.56 (18) |
N2—N1—C1 | 110.23 (15) | O1—C21—C22 | 108.89 (16) |
N2—N1—C9 | 119.62 (14) | N1—C1—H1 | 127.00 |
C1—N1—C9 | 130.03 (14) | C2—C1—H1 | 127.00 |
N1—N2—N3 | 107.05 (16) | C3—C4—H4 | 120.00 |
N2—N3—C2 | 109.44 (17) | C5—C4—H4 | 120.00 |
N1—C1—C2 | 105.29 (15) | C4—C5—H5 | 120.00 |
N3—C2—C1 | 107.98 (16) | C6—C5—H5 | 120.00 |
N3—C2—C3 | 122.21 (17) | C5—C6—H6 | 120.00 |
C1—C2—C3 | 129.81 (17) | C7—C6—H6 | 120.00 |
C2—C3—C4 | 121.23 (16) | C6—C7—H7 | 120.00 |
C2—C3—C8 | 120.43 (17) | C8—C7—H7 | 120.00 |
C4—C3—C8 | 118.32 (17) | C3—C8—H8 | 120.00 |
C3—C4—C5 | 120.68 (18) | C7—C8—H8 | 120.00 |
C4—C5—C6 | 120.3 (2) | C9—C10—H10 | 120.00 |
C5—C6—C7 | 119.8 (2) | C11—C10—H10 | 120.00 |
C6—C7—C8 | 120.5 (2) | C10—C11—H11 | 119.00 |
C3—C8—C7 | 120.5 (2) | C12—C11—H11 | 119.00 |
N1—C9—C10 | 119.43 (16) | C12—C13—H13 | 119.00 |
N1—C9—C14 | 120.22 (16) | C14—C13—H13 | 119.00 |
C10—C9—C14 | 120.31 (17) | C9—C14—H14 | 120.00 |
C9—C10—C11 | 119.58 (17) | C13—C14—H14 | 120.00 |
C10—C11—C12 | 121.50 (17) | C16—C17—H17 | 121.00 |
C11—C12—C13 | 117.70 (16) | C18—C17—H17 | 121.00 |
C11—C12—C15 | 121.66 (16) | C18—C19—H19 | 121.00 |
C13—C12—C15 | 120.64 (16) | C20—C19—H19 | 121.00 |
C12—C13—C14 | 121.45 (17) | C15—C20—H20 | 119.00 |
C9—C14—C13 | 119.32 (17) | C19—C20—H20 | 119.00 |
C12—C15—C16 | 121.32 (16) | O1—C21—H21A | 110.00 |
C12—C15—C20 | 120.59 (16) | O1—C21—H21B | 110.00 |
C16—C15—C20 | 118.05 (16) | C22—C21—H21A | 110.00 |
O1—C16—C15 | 117.13 (15) | C22—C21—H21B | 110.00 |
O1—C16—C17 | 123.12 (17) | H21A—C21—H21B | 108.00 |
C15—C16—C17 | 119.72 (16) | C21—C22—H22A | 109.00 |
C16—C17—C18 | 118.82 (18) | C21—C22—H22B | 109.00 |
F1—C18—C17 | 117.08 (19) | C21—C22—H22C | 109.00 |
F1—C18—C19 | 119.37 (19) | H22A—C22—H22B | 109.00 |
C17—C18—C19 | 123.55 (19) | H22A—C22—H22C | 109.00 |
C18—C19—C20 | 117.3 (2) | H22B—C22—H22C | 110.00 |
C21—O1—C16—C15 | 171.58 (16) | N1—C9—C10—C11 | 173.95 (17) |
C21—O1—C16—C17 | −6.3 (2) | C14—C9—C10—C11 | −3.5 (3) |
C16—O1—C21—C22 | −175.08 (16) | N1—C9—C14—C13 | −174.70 (17) |
C1—N1—N2—N3 | −0.7 (2) | C10—C9—C14—C13 | 2.8 (3) |
C9—N1—N2—N3 | −177.13 (16) | C9—C10—C11—C12 | 0.8 (3) |
N2—N1—C1—C2 | 0.9 (2) | C10—C11—C12—C13 | 2.7 (3) |
C9—N1—C1—C2 | 176.86 (17) | C10—C11—C12—C15 | −177.98 (17) |
N2—N1—C9—C10 | −19.9 (2) | C11—C12—C13—C14 | −3.4 (3) |
N2—N1—C9—C14 | 157.63 (17) | C15—C12—C13—C14 | 177.19 (17) |
C1—N1—C9—C10 | 164.46 (18) | C11—C12—C15—C16 | 55.8 (2) |
C1—N1—C9—C14 | −18.1 (3) | C11—C12—C15—C20 | −126.4 (2) |
N1—N2—N3—C2 | 0.2 (2) | C13—C12—C15—C16 | −124.8 (2) |
N2—N3—C2—C1 | 0.4 (2) | C13—C12—C15—C20 | 53.0 (2) |
N2—N3—C2—C3 | −178.95 (17) | C12—C13—C14—C9 | 0.8 (3) |
N1—C1—C2—N3 | −0.8 (2) | C12—C15—C16—O1 | −1.1 (3) |
N1—C1—C2—C3 | 178.51 (18) | C12—C15—C16—C17 | 176.85 (17) |
N3—C2—C3—C4 | 159.79 (19) | C20—C15—C16—O1 | −178.96 (16) |
N3—C2—C3—C8 | −18.8 (3) | C20—C15—C16—C17 | −1.0 (3) |
C1—C2—C3—C4 | −19.4 (3) | C12—C15—C20—C19 | −178.16 (18) |
C1—C2—C3—C8 | 162.00 (19) | C16—C15—C20—C19 | −0.3 (3) |
C2—C3—C4—C5 | −178.43 (18) | O1—C16—C17—C18 | 179.02 (18) |
C8—C3—C4—C5 | 0.2 (3) | C15—C16—C17—C18 | 1.2 (3) |
C2—C3—C8—C7 | 178.86 (18) | C16—C17—C18—F1 | −179.11 (17) |
C4—C3—C8—C7 | 0.2 (3) | C16—C17—C18—C19 | −0.1 (3) |
C3—C4—C5—C6 | −0.3 (3) | F1—C18—C19—C20 | 177.84 (18) |
C4—C5—C6—C7 | −0.2 (3) | C17—C18—C19—C20 | −1.2 (3) |
C5—C6—C7—C8 | 0.6 (3) | C18—C19—C20—C15 | 1.4 (3) |
C6—C7—C8—C3 | −0.6 (3) |
Acknowledgements
The authors are thankful to IOE, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction facility.
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