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The title compound, C16H10Cl2N4O, has been synthesized as a potent fungicidal agent and plant growth regulatory agent, and its crystal structure was determined. In the crystal structure, weak inter­molecular C—H...Cl inter­actions are found. The dihedral angles between the planes of the pyridine and triazole rings, and between the substituted phenyl and triazole rings, are 82.4 (2) and 118.8 (3)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031454/at6036sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031454/at6036Isup2.hkl
Contains datablock I

CCDC reference: 289628

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.087
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.10 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

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.

(Z)-3-(2,6-Dichlorophenyl)-1-(pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)prop- 2-en-1-one top
Crystal data top
C16H10Cl2N4OF(000) = 704
Mr = 345.18Dx = 1.431 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2848 reflections
a = 8.0749 (14) Åθ = 2.3–23.8°
b = 19.795 (3) ŵ = 0.41 mm1
c = 10.1321 (17) ÅT = 294 K
β = 98.280 (2)°Block, white
V = 1602.7 (5) Å30.46 × 0.32 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX-II CCD area-detector
diffractometer
2837 independent reflections
Radiation source: fine-focus sealed tube2308 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.760, Tmax = 0.928k = 2322
8638 measured reflectionsl = 1012
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0442P)2 + 0.2713P]
where P = (Fo2 + 2Fc2)/3
2837 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
Cl10.53194 (6)0.22862 (2)0.00434 (5)0.05926 (17)
Cl20.26413 (7)0.01068 (2)0.10790 (5)0.06224 (18)
O10.34217 (17)0.17995 (8)0.48814 (13)0.0645 (4)
N10.17839 (16)0.13916 (6)0.24507 (13)0.0366 (3)
N20.10677 (19)0.17336 (8)0.13496 (16)0.0528 (4)
N30.09093 (19)0.12797 (8)0.24402 (17)0.0532 (4)
N40.77331 (19)0.02328 (8)0.50587 (15)0.0472 (4)
C10.4274 (2)0.15470 (8)0.05478 (17)0.0394 (4)
C20.3780 (2)0.14415 (10)0.18899 (18)0.0493 (5)
H20.39940.17650.25090.059*
C30.2969 (2)0.08540 (10)0.23022 (18)0.0535 (5)
H30.26470.07760.32080.064*
C40.2628 (2)0.03793 (10)0.13900 (19)0.0520 (5)
H40.20830.00200.16740.062*
C50.3100 (2)0.05014 (9)0.00504 (17)0.0422 (4)
C60.39462 (19)0.10862 (8)0.04147 (15)0.0355 (4)
C70.4515 (2)0.12143 (8)0.18426 (16)0.0364 (4)
H70.56650.12170.21180.044*
C80.3544 (2)0.13266 (8)0.27722 (16)0.0351 (4)
C90.0523 (2)0.16463 (11)0.1403 (2)0.0579 (5)
H90.13450.18260.07620.069*
C100.0572 (2)0.11358 (9)0.30755 (19)0.0454 (4)
H100.07620.08870.38620.054*
C110.4217 (2)0.14637 (8)0.41929 (16)0.0401 (4)
C120.5868 (2)0.11800 (8)0.47684 (16)0.0366 (4)
C130.6351 (2)0.05341 (8)0.44660 (16)0.0398 (4)
H130.56680.02960.38080.048*
C140.8701 (2)0.05943 (10)0.59702 (19)0.0501 (5)
H140.96760.03940.63950.060*
C150.8360 (2)0.12404 (10)0.63258 (19)0.0532 (5)
H150.90960.14730.69560.064*
C160.6896 (2)0.15388 (9)0.57269 (18)0.0476 (4)
H160.66100.19730.59650.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0578 (3)0.0467 (3)0.0701 (3)0.0132 (2)0.0014 (2)0.0085 (2)
Cl20.0746 (4)0.0493 (3)0.0644 (3)0.0157 (2)0.0152 (3)0.0077 (2)
O10.0566 (9)0.0838 (10)0.0508 (8)0.0319 (8)0.0000 (6)0.0192 (7)
N10.0306 (7)0.0379 (7)0.0410 (8)0.0041 (6)0.0045 (6)0.0051 (6)
N20.0374 (9)0.0614 (10)0.0585 (10)0.0082 (7)0.0031 (7)0.0252 (8)
N30.0357 (9)0.0566 (10)0.0678 (11)0.0036 (7)0.0095 (8)0.0026 (8)
N40.0412 (9)0.0476 (9)0.0509 (9)0.0090 (7)0.0002 (7)0.0032 (7)
C10.0315 (9)0.0426 (9)0.0439 (10)0.0005 (7)0.0046 (7)0.0033 (7)
C20.0468 (11)0.0601 (12)0.0410 (10)0.0032 (9)0.0066 (8)0.0117 (8)
C30.0531 (12)0.0686 (13)0.0371 (10)0.0011 (10)0.0011 (8)0.0043 (9)
C40.0489 (12)0.0532 (11)0.0515 (12)0.0049 (9)0.0008 (9)0.0107 (9)
C50.0384 (10)0.0428 (10)0.0457 (10)0.0013 (7)0.0068 (8)0.0018 (8)
C60.0280 (9)0.0414 (9)0.0370 (9)0.0029 (7)0.0048 (7)0.0012 (7)
C70.0306 (9)0.0394 (9)0.0384 (9)0.0010 (7)0.0020 (7)0.0021 (7)
C80.0325 (9)0.0336 (8)0.0385 (9)0.0037 (7)0.0024 (7)0.0038 (7)
C90.0337 (11)0.0688 (13)0.0687 (13)0.0080 (9)0.0008 (9)0.0164 (11)
C100.0428 (11)0.0449 (10)0.0502 (11)0.0001 (8)0.0125 (8)0.0051 (8)
C110.0398 (10)0.0401 (9)0.0405 (9)0.0077 (8)0.0058 (8)0.0009 (7)
C120.0350 (9)0.0413 (9)0.0338 (9)0.0027 (7)0.0061 (7)0.0017 (7)
C130.0376 (10)0.0424 (10)0.0387 (9)0.0025 (7)0.0033 (7)0.0011 (7)
C140.0365 (10)0.0596 (12)0.0520 (11)0.0061 (9)0.0011 (8)0.0100 (9)
C150.0439 (11)0.0595 (12)0.0523 (11)0.0077 (9)0.0064 (9)0.0042 (9)
C160.0479 (11)0.0440 (10)0.0495 (10)0.0017 (8)0.0022 (9)0.0059 (8)
Geometric parameters (Å, º) top
Cl1—C11.7292 (17)C4—H40.9300
Cl2—C51.7373 (17)C5—C61.392 (2)
O1—C111.212 (2)C6—C71.475 (2)
N1—C101.339 (2)C7—C81.328 (2)
N1—N21.3608 (19)C7—H70.9300
N1—C81.418 (2)C8—C111.489 (2)
N2—C91.305 (2)C9—H90.9300
N3—C101.306 (2)C10—H100.9300
N3—C91.350 (2)C11—C121.486 (2)
N4—C131.330 (2)C12—C161.380 (2)
N4—C141.329 (2)C12—C131.384 (2)
C1—C21.377 (2)C13—H130.9300
C1—C61.388 (2)C14—C151.367 (3)
C2—C31.370 (3)C14—H140.9300
C2—H20.9300C15—C161.381 (3)
C3—C41.374 (3)C15—H150.9300
C3—H30.9300C16—H160.9300
C4—C51.377 (3)
C10—N1—N2108.82 (14)C7—C8—N1121.81 (15)
C10—N1—C8129.33 (14)C7—C8—C11123.08 (15)
N2—N1—C8121.82 (13)N1—C8—C11114.82 (13)
C9—N2—N1101.82 (14)N2—C9—N3116.27 (17)
C10—N3—C9101.71 (15)N2—C9—H9121.9
C13—N4—C14116.31 (16)N3—C9—H9121.9
C2—C1—C6122.45 (16)N3—C10—N1111.37 (16)
C2—C1—Cl1118.68 (13)N3—C10—H10124.3
C6—C1—Cl1118.86 (13)N1—C10—H10124.3
C3—C2—C1119.19 (17)O1—C11—C12120.06 (15)
C3—C2—H2120.4O1—C11—C8120.44 (15)
C1—C2—H2120.4C12—C11—C8119.49 (14)
C2—C3—C4120.60 (17)C16—C12—C13118.07 (15)
C2—C3—H3119.7C16—C12—C11119.77 (15)
C4—C3—H3119.7C13—C12—C11121.88 (15)
C3—C4—C5119.29 (17)N4—C13—C12124.03 (16)
C3—C4—H4120.4N4—C13—H13118.0
C5—C4—H4120.4C12—C13—H13118.0
C4—C5—C6122.17 (16)N4—C14—C15124.48 (18)
C4—C5—Cl2118.20 (14)N4—C14—H14117.8
C6—C5—Cl2119.62 (13)C15—C14—H14117.8
C1—C6—C5116.28 (15)C14—C15—C16118.44 (18)
C1—C6—C7120.78 (14)C14—C15—H15120.8
C5—C6—C7122.92 (14)C16—C15—H15120.8
C8—C7—C6126.28 (15)C12—C16—C15118.64 (17)
C8—C7—H7116.9C12—C16—H16120.7
C6—C7—H7116.9C15—C16—H16120.7
C10—N1—N2—C90.66 (19)N2—N1—C8—C11133.78 (16)
C8—N1—N2—C9177.43 (16)N1—N2—C9—N30.1 (2)
C6—C1—C2—C31.6 (3)C10—N3—C9—N20.4 (2)
Cl1—C1—C2—C3179.20 (15)C9—N3—C10—N10.8 (2)
C1—C2—C3—C41.0 (3)N2—N1—C10—N31.0 (2)
C2—C3—C4—C50.4 (3)C8—N1—C10—N3176.90 (15)
C3—C4—C5—C61.3 (3)C7—C8—C11—O1152.18 (18)
C3—C4—C5—Cl2179.69 (14)N1—C8—C11—O121.7 (2)
C2—C1—C6—C50.7 (2)C7—C8—C11—C1228.4 (2)
Cl1—C1—C6—C5179.91 (12)N1—C8—C11—C12157.68 (14)
C2—C1—C6—C7179.26 (16)O1—C11—C12—C1634.3 (3)
Cl1—C1—C6—C71.6 (2)C8—C11—C12—C16146.31 (16)
C4—C5—C6—C10.8 (3)O1—C11—C12—C13139.53 (18)
Cl2—C5—C6—C1179.72 (12)C8—C11—C12—C1339.9 (2)
C4—C5—C6—C7177.73 (16)C14—N4—C13—C121.7 (3)
Cl2—C5—C6—C71.2 (2)C16—C12—C13—N41.2 (3)
C1—C6—C7—C8113.59 (19)C11—C12—C13—N4172.69 (16)
C5—C6—C7—C868.0 (2)C13—N4—C14—C150.2 (3)
C6—C7—C8—N15.4 (3)N4—C14—C15—C161.5 (3)
C6—C7—C8—C11178.94 (15)C13—C12—C16—C150.6 (3)
C10—N1—C8—C7137.44 (18)C11—C12—C16—C15174.68 (16)
N2—N1—C8—C740.2 (2)C14—C15—C16—C121.9 (3)
C10—N1—C8—C1148.6 (2)
 

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