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The title compound, C17H16N4O2, a potent fungicidal agent, has been synthesized and its crystal structure determined. The dihedral angles between the planes of the pyridinyl and triazole rings, and between the substituted phenyl and triazole rings are 82.7 (2)° and 77.0 (3)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030400/wn6377sup1.cif
Contains datablocks 050706c, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030400/wn6377Isup2.hkl
Contains datablock I

CCDC reference: 287746

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.126
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL023_ALERT_1_A There is a mismatched ^ on line 381 Refinement of F2^ against ALL reflections. The weighted R-factor wR and If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 382 goodness of fit S are based on F2^, conventional R-factors R are based If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 383 on F, with F set to zero for negative F2^. The threshold expression of If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C PUBL023_ALERT_1_A There is a mismatched ^ on line 387 on F2^ are statistically about twice as large as those based on F, and R- If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C
4 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

It is well known that compounds containing the 1H-1,2,4-triazole ring system are highly active as fungicides (Buchenauer, 1979), especially against the Basidiomycete and Ascomycete groups of fungi. These compounds are known to inhibit the biosynthesis of ergosterol in fungi (Hiroshi et al., 1995; Fang et al., 2003a,b). They are widely applied in the fields of medication and plant protection. In addition, compounds containing the pyridinyl ring are becoming more and more important in the development of medicines and fungicides, due to their excellent biological activities (Xiong et al., 2001; Zhao et al., 2004; Kurahashi et al., 1997; Oliver et al., 2000 not in list - do you mean Wagner et al., 2000?).

As a continuation of our interest in searching for novel 1H-1,2,4-triazole compounds with potent fungicidal activities, we have sought to synthesize 1H-1,2,4- triazole compounds involving pyridinyl units. We report here the structure of 2-(2,3-dimethylphenoxy)-1-(pyridin-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone, (I).

Fig.1 shows the molecular structure of (I); it contains three planar ring systems, viz. the pyridinyl ring (p1), the triazole ring (p2) and the substituted phenyl ring (p3). The dihedral angles between p1 and p2, and between p3 and p2 are 82.7 (2)° and 77.0 (3)°, respectively. The bond lengths and bond angles are unexceptional.

Experimental top

2-Bromo-1-(pyridin-2-yl)-2-(1H-1,2,4-triazol-1-yl) ethanone hydrobromide (5 mmol) was dissolved in acetone (15 ml). A mixture of 2,3-dimethylphenol (6 mmol), Et3N (10 mmol) and acetone (20 ml) was then added dropwise, while cooling on an ice-bath. The reaction mixture was stirred at room temperature for 2.5 h (monitored by TLC). The solution was filtered, and the filtrate was evaporated under reduced pressure. The residue was dissolved in 25 ml chloroform and washed with water (3 x 20 ml) and then adjusted to pH = 7 with 2 N aqueous NaOH. The organic layer was separated and washed with water (3 x 20 ml). The combined organic layer was dried over anhydrous Na2SO4. After removal of the solvent, the residue was separated by column chromatography on silica gel (200–300 mesh, petroleum ether/ethyl acetate (v/v = 4:1 as eluent) and recrystallized from petroleum ether/ethyl acetate (v/v) = 1:1) to give a yellow crystal (yield 62%).

Refinement top

All H atoms were placed in calculated positions and were refined isotropically, with Uiso(H) = 1.2Ueq(C), using a riding model with C—H = 0.93–0.98 Å.

Computing details top

Data collection: SMART (Bruker,1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound.
2-(2,3-dimethylphenoxy)-1-(pyridin-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone top
Crystal data top
C17H16N4O2Z = 2
Mr = 308.34F(000) = 324
Triclinic, P1Dx = 1.312 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 7.700 (2) ÅCell parameters from 1220 reflections
b = 9.989 (3) Åθ = 2.8–24.3°
c = 11.230 (3) ŵ = 0.09 mm1
α = 102.490 (4)°T = 294 K
β = 108.484 (4)°Hexagonal fragment, yellow
γ = 97.688 (4)°0.24 × 0.18 × 0.10 mm
V = 780.5 (3) Å3
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
2728 independent reflections
Radiation source: fine-focus sealed tube1738 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 98
Tmin = 0.978, Tmax = 0.991k = 911
3976 measured reflectionsl = 1213
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0632P)2 + 0.0431P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.004
2728 reflectionsΔρmax = 0.22 e Å3
211 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.045 (6)
Crystal data top
C17H16N4O2γ = 97.688 (4)°
Mr = 308.34V = 780.5 (3) Å3
Triclinic, P1Z = 2
a = 7.700 (2) ÅMo Kα radiation
b = 9.989 (3) ŵ = 0.09 mm1
c = 11.230 (3) ÅT = 294 K
α = 102.490 (4)°0.24 × 0.18 × 0.10 mm
β = 108.484 (4)°
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
2728 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
1738 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.991Rint = 0.019
3976 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
2728 reflectionsΔρmin = 0.20 e Å3
211 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3503 (2)0.39104 (16)0.72933 (17)0.0704 (5)
O20.27927 (18)0.11512 (13)0.66461 (13)0.0489 (4)
N10.0697 (2)0.33687 (18)0.78993 (17)0.0586 (5)
N20.2327 (2)0.15222 (16)0.86527 (15)0.0452 (4)
N30.4139 (2)0.19659 (19)0.94906 (17)0.0610 (5)
N40.2356 (3)0.0798 (2)1.03547 (19)0.0694 (6)
C10.1926 (3)0.4064 (3)0.8211 (2)0.0727 (7)
H10.30400.35460.81880.087*
C20.1633 (4)0.5501 (3)0.8564 (3)0.0771 (8)
H20.25350.59420.87630.092*
C30.0014 (4)0.6263 (3)0.8618 (3)0.0849 (8)
H30.02230.72390.88690.102*
C40.1287 (4)0.5584 (2)0.8298 (2)0.0698 (7)
H40.24110.60910.83260.084*
C50.0888 (3)0.4146 (2)0.79375 (19)0.0474 (5)
C60.2202 (3)0.3355 (2)0.75187 (19)0.0475 (5)
C70.1776 (3)0.1769 (2)0.73702 (18)0.0440 (5)
H70.04310.13780.69010.053*
C80.1316 (3)0.0838 (2)0.9189 (2)0.0585 (6)
H80.00390.04400.87900.070*
C90.4060 (3)0.1486 (3)1.0477 (2)0.0663 (7)
H90.51160.16141.12160.080*
C100.2562 (3)0.03086 (19)0.63485 (17)0.0412 (5)
C110.0853 (3)0.1201 (2)0.6035 (2)0.0553 (6)
H110.01980.08460.60480.066*
C120.0738 (3)0.2628 (2)0.5701 (2)0.0651 (7)
H120.03950.32470.55020.078*
C130.2294 (4)0.3141 (2)0.5663 (2)0.0644 (6)
H130.21920.41080.54290.077*
C140.4012 (3)0.2256 (2)0.59628 (19)0.0521 (5)
C150.5690 (3)0.2855 (3)0.5906 (3)0.0830 (8)
H15A0.53980.38490.57960.124*
H15B0.67370.24170.67040.124*
H15C0.60020.26820.51830.124*
C160.4162 (3)0.0802 (2)0.63281 (17)0.0423 (5)
C170.5990 (3)0.0222 (2)0.6706 (2)0.0561 (6)
H17A0.57500.10710.64840.084*
H17B0.67380.01820.62460.084*
H17C0.66510.04300.76290.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0616 (10)0.0586 (10)0.1126 (14)0.0156 (8)0.0496 (10)0.0376 (9)
O20.0507 (8)0.0460 (8)0.0626 (9)0.0161 (7)0.0314 (7)0.0201 (7)
N10.0427 (10)0.0571 (11)0.0768 (13)0.0144 (9)0.0243 (9)0.0133 (9)
N20.0417 (9)0.0467 (10)0.0522 (10)0.0106 (8)0.0198 (8)0.0186 (8)
N30.0458 (10)0.0725 (13)0.0590 (12)0.0058 (9)0.0110 (9)0.0227 (10)
N40.0707 (13)0.0804 (14)0.0664 (13)0.0140 (11)0.0263 (11)0.0378 (11)
C10.0522 (14)0.0752 (18)0.0939 (19)0.0244 (13)0.0310 (13)0.0162 (14)
C20.0832 (19)0.0765 (19)0.0928 (19)0.0466 (16)0.0441 (16)0.0291 (15)
C30.113 (2)0.0545 (15)0.111 (2)0.0394 (16)0.0599 (19)0.0277 (15)
C40.0825 (18)0.0515 (15)0.0919 (18)0.0182 (13)0.0465 (15)0.0273 (13)
C50.0492 (12)0.0463 (12)0.0514 (12)0.0147 (10)0.0186 (10)0.0194 (9)
C60.0422 (11)0.0486 (12)0.0557 (13)0.0115 (10)0.0181 (10)0.0208 (10)
C70.0381 (10)0.0485 (12)0.0505 (12)0.0129 (9)0.0189 (9)0.0172 (9)
C80.0513 (12)0.0641 (14)0.0669 (15)0.0076 (11)0.0245 (12)0.0294 (12)
C90.0640 (16)0.0756 (16)0.0565 (15)0.0133 (13)0.0146 (12)0.0243 (12)
C100.0455 (11)0.0407 (11)0.0395 (11)0.0109 (9)0.0167 (9)0.0123 (8)
C110.0454 (12)0.0575 (14)0.0613 (14)0.0073 (11)0.0201 (10)0.0139 (11)
C120.0602 (15)0.0546 (15)0.0704 (16)0.0039 (12)0.0232 (12)0.0073 (12)
C130.0843 (18)0.0411 (12)0.0627 (15)0.0102 (13)0.0257 (13)0.0069 (10)
C140.0613 (14)0.0509 (13)0.0457 (12)0.0173 (11)0.0191 (10)0.0134 (10)
C150.0861 (19)0.0667 (16)0.103 (2)0.0377 (15)0.0391 (16)0.0157 (15)
C160.0442 (11)0.0490 (12)0.0347 (10)0.0118 (9)0.0131 (9)0.0140 (9)
C170.0442 (12)0.0638 (14)0.0618 (14)0.0144 (11)0.0195 (10)0.0178 (11)
Geometric parameters (Å, º) top
O1—C61.203 (2)C7—H70.9800
O2—C101.397 (2)C8—H80.9300
O2—C71.403 (2)C9—H90.9300
N1—C11.334 (3)C10—C111.381 (3)
N1—C51.339 (2)C10—C161.391 (3)
N2—C81.330 (2)C11—C121.376 (3)
N2—N31.360 (2)C11—H110.9300
N2—C71.452 (2)C12—C131.374 (3)
N3—C91.314 (3)C12—H120.9300
N4—C81.313 (3)C13—C141.386 (3)
N4—C91.347 (3)C13—H130.9300
C1—C21.371 (3)C14—C161.399 (3)
C1—H10.9300C14—C151.508 (3)
C2—C31.347 (3)C15—H15A0.9600
C2—H20.9300C15—H15B0.9600
C3—C41.377 (3)C15—H15C0.9600
C3—H30.9300C16—C171.502 (3)
C4—C51.369 (3)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C5—C61.492 (3)C17—H17C0.9600
C6—C71.535 (3)
C10—O2—C7117.54 (14)N3—C9—N4116.0 (2)
C1—N1—C5116.73 (19)N3—C9—H9122.0
C8—N2—N3109.42 (17)N4—C9—H9122.0
C8—N2—C7129.87 (17)C11—C10—C16122.31 (18)
N3—N2—C7120.65 (15)C11—C10—O2122.58 (17)
C9—N3—N2101.54 (17)C16—C10—O2115.04 (16)
C8—N4—C9101.86 (18)C12—C11—C10118.7 (2)
N1—C1—C2123.5 (2)C12—C11—H11120.7
N1—C1—H1118.3C10—C11—H11120.7
C2—C1—H1118.3C13—C12—C11120.1 (2)
C3—C2—C1118.8 (2)C13—C12—H12120.0
C3—C2—H2120.6C11—C12—H12120.0
C1—C2—H2120.6C12—C13—C14121.8 (2)
C2—C3—C4119.5 (2)C12—C13—H13119.1
C2—C3—H3120.3C14—C13—H13119.1
C4—C3—H3120.3C13—C14—C16118.9 (2)
C5—C4—C3118.5 (2)C13—C14—C15120.3 (2)
C5—C4—H4120.8C16—C14—C15120.8 (2)
C3—C4—H4120.8C14—C15—H15A109.5
N1—C5—C4123.0 (2)C14—C15—H15B109.5
N1—C5—C6116.14 (17)H15A—C15—H15B109.5
C4—C5—C6120.79 (19)C14—C15—H15C109.5
O1—C6—C5122.65 (18)H15A—C15—H15C109.5
O1—C6—C7121.63 (18)H15B—C15—H15C109.5
C5—C6—C7115.72 (16)C10—C16—C14118.28 (18)
O2—C7—N2110.86 (14)C10—C16—C17119.83 (17)
O2—C7—C6107.59 (15)C14—C16—C17121.89 (18)
N2—C7—C6109.57 (15)C16—C17—H17A109.5
O2—C7—H7109.6C16—C17—H17B109.5
N2—C7—H7109.6H17A—C17—H17B109.5
C6—C7—H7109.6C16—C17—H17C109.5
N4—C8—N2111.16 (19)H17A—C17—H17C109.5
N4—C8—H8124.4H17B—C17—H17C109.5
N2—C8—H8124.4
C8—N2—N3—C90.6 (2)C5—C6—C7—N275.3 (2)
C7—N2—N3—C9176.93 (17)C9—N4—C8—N20.7 (3)
C5—N1—C1—C20.3 (3)N3—N2—C8—N40.1 (2)
N1—C1—C2—C30.9 (4)C7—N2—C8—N4177.32 (18)
C1—C2—C3—C41.1 (4)N2—N3—C9—N41.1 (3)
C2—C3—C4—C50.2 (4)C8—N4—C9—N31.2 (3)
C1—N1—C5—C41.2 (3)C7—O2—C10—C1137.7 (2)
C1—N1—C5—C6176.88 (18)C7—O2—C10—C16145.38 (16)
C3—C4—C5—N11.0 (3)C16—C10—C11—C120.6 (3)
C3—C4—C5—C6177.0 (2)O2—C10—C11—C12177.31 (18)
N1—C5—C6—O1166.9 (2)C10—C11—C12—C131.1 (3)
C4—C5—C6—O111.2 (3)C11—C12—C13—C140.5 (3)
N1—C5—C6—C712.1 (3)C12—C13—C14—C160.7 (3)
C4—C5—C6—C7169.73 (18)C12—C13—C14—C15179.8 (2)
C10—O2—C7—N262.5 (2)C11—C10—C16—C140.6 (3)
C10—O2—C7—C6177.70 (14)O2—C10—C16—C14176.33 (16)
C8—N2—C7—O2118.3 (2)C11—C10—C16—C17178.75 (18)
N3—N2—C7—O258.7 (2)O2—C10—C16—C174.3 (2)
C8—N2—C7—C6123.1 (2)C13—C14—C16—C101.3 (3)
N3—N2—C7—C659.9 (2)C15—C14—C16—C10179.28 (18)
O1—C6—C7—O215.0 (3)C13—C14—C16—C17178.13 (18)
C5—C6—C7—O2164.13 (15)C15—C14—C16—C171.3 (3)
O1—C6—C7—N2105.6 (2)

Experimental details

Crystal data
Chemical formulaC17H16N4O2
Mr308.34
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)7.700 (2), 9.989 (3), 11.230 (3)
α, β, γ (°)102.490 (4), 108.484 (4), 97.688 (4)
V3)780.5 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.24 × 0.18 × 0.10
Data collection
DiffractometerBruker SMART 1000 CCD area detector
diffractometer
Absorption correctionMulti-scan
SADABS (Sheldrick, 1996)
Tmin, Tmax0.978, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
3976, 2728, 1738
Rint0.019
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.126, 1.03
No. of reflections2728
No. of parameters211
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.20

Computer programs: SMART (Bruker,1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

 

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