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The title compound, C15H10FN3OS, has been synthesized as a potent fungicidal agent. In the crystal structure, weak inter­molecular C—H...N and N—H...N hydrogen bonds are found. The dihedral angles between the pyridine and thia­zole rings, and between the benzene and thia­zole rings, are 4.3 (2) and 19.5 (3)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043704/is2092sup1.cif
Contains datablocks 060228c, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043704/is2092Isup2.hkl
Contains datablock I

CCDC reference: 627816

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.102
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
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 0 ALERT type 5 Informative message, check

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.

4-fluoro-N-(4-(pyridin-4-yl)thiazol-2-yl)benzamide top
Crystal data top
C15H10FN3OSF(000) = 616
Mr = 299.32Dx = 1.492 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 1902 reflections
a = 8.430 (3) Åθ = 2.4–24.3°
b = 13.352 (4) ŵ = 0.26 mm1
c = 11.853 (4) ÅT = 294 K
β = 92.838 (6)°Block, colorless
V = 1332.5 (8) Å30.22 × 0.20 × 0.12 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer
2744 independent reflections
Radiation source: fine-focus sealed tube1809 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 710
Tmin = 0.944, Tmax = 0.965k = 1516
7444 measured reflectionsl = 149
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0498P)2]
where P = (Fo2 + 2Fc2)/3
2744 reflections(Δ/σ)max = 0.002
190 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.27 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
S10.72252 (7)0.04849 (4)1.09421 (4)0.04088 (19)
F10.23928 (19)0.51387 (10)0.95423 (11)0.0692 (5)
O10.56355 (19)0.12162 (11)1.14055 (12)0.0492 (4)
N11.1545 (2)0.25621 (13)0.68833 (14)0.0420 (5)
N20.82453 (19)0.00505 (12)0.89854 (13)0.0352 (4)
N30.6855 (2)0.12762 (12)0.97554 (13)0.0375 (4)
H30.71020.16510.92010.045*
C10.9654 (2)0.15679 (14)0.84179 (16)0.0334 (5)
C21.0122 (3)0.11045 (15)0.74430 (16)0.0395 (5)
H20.98070.04510.72770.047*
C31.1063 (3)0.16239 (16)0.67184 (17)0.0422 (5)
H3A1.13780.12950.60750.051*
C41.1070 (3)0.30079 (16)0.78135 (19)0.0460 (6)
H41.13810.36670.79480.055*
C51.0143 (3)0.25495 (16)0.85882 (18)0.0447 (6)
H50.98480.28980.92240.054*
C60.8716 (2)0.10238 (14)0.92352 (16)0.0340 (5)
C70.8263 (2)0.13682 (15)1.02476 (16)0.0389 (5)
H70.84900.20061.05270.047*
C80.7458 (2)0.03127 (14)0.98046 (16)0.0337 (5)
C90.5889 (2)0.16659 (15)1.05381 (17)0.0363 (5)
C100.5099 (2)0.26391 (15)1.02490 (16)0.0357 (5)
C110.4320 (3)0.31341 (16)1.10943 (17)0.0478 (6)
H110.44000.28881.18290.057*
C120.3434 (3)0.39816 (17)1.08610 (18)0.0532 (6)
H120.29320.43171.14310.064*
C130.3310 (3)0.43172 (16)0.97740 (19)0.0469 (6)
C140.4064 (3)0.38651 (16)0.89139 (17)0.0437 (6)
H140.39730.41190.81830.052*
C150.4964 (2)0.30235 (15)0.91592 (16)0.0387 (5)
H150.54890.27080.85860.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0478 (4)0.0425 (3)0.0333 (3)0.0026 (3)0.0115 (2)0.0009 (2)
F10.0910 (12)0.0590 (9)0.0576 (9)0.0324 (8)0.0046 (8)0.0004 (7)
O10.0604 (10)0.0518 (10)0.0369 (8)0.0075 (8)0.0167 (7)0.0052 (7)
N10.0460 (12)0.0372 (10)0.0439 (11)0.0032 (9)0.0136 (9)0.0039 (8)
N20.0371 (10)0.0355 (10)0.0340 (9)0.0021 (8)0.0105 (8)0.0003 (7)
N30.0429 (11)0.0343 (10)0.0367 (10)0.0017 (8)0.0137 (8)0.0009 (8)
C10.0318 (11)0.0335 (11)0.0348 (11)0.0042 (9)0.0026 (9)0.0027 (9)
C20.0472 (13)0.0325 (11)0.0393 (12)0.0010 (10)0.0075 (10)0.0013 (9)
C30.0518 (14)0.0370 (12)0.0390 (12)0.0048 (11)0.0143 (10)0.0017 (10)
C40.0529 (15)0.0339 (12)0.0521 (14)0.0051 (11)0.0109 (11)0.0010 (11)
C50.0545 (15)0.0398 (12)0.0410 (12)0.0008 (11)0.0141 (11)0.0042 (10)
C60.0344 (12)0.0325 (11)0.0354 (11)0.0055 (9)0.0053 (9)0.0020 (9)
C70.0417 (13)0.0369 (12)0.0386 (12)0.0020 (10)0.0074 (10)0.0007 (10)
C80.0326 (11)0.0332 (11)0.0359 (11)0.0076 (9)0.0067 (9)0.0018 (9)
C90.0360 (12)0.0407 (12)0.0326 (11)0.0040 (10)0.0061 (9)0.0045 (9)
C100.0373 (12)0.0378 (12)0.0324 (11)0.0033 (10)0.0056 (9)0.0060 (9)
C110.0624 (16)0.0530 (14)0.0286 (11)0.0081 (13)0.0095 (11)0.0020 (10)
C120.0697 (17)0.0536 (15)0.0373 (13)0.0164 (13)0.0127 (11)0.0094 (11)
C130.0522 (15)0.0416 (13)0.0469 (14)0.0082 (11)0.0024 (11)0.0014 (10)
C140.0509 (14)0.0483 (14)0.0325 (12)0.0005 (12)0.0061 (10)0.0015 (10)
C150.0411 (13)0.0438 (12)0.0321 (11)0.0001 (11)0.0107 (9)0.0075 (10)
Geometric parameters (Å, º) top
S1—C71.704 (2)C4—C51.378 (3)
S1—C81.737 (2)C4—H40.9300
F1—C131.362 (2)C5—H50.9300
O1—C91.219 (2)C6—C71.357 (3)
N1—C31.328 (3)C7—H70.9300
N1—C41.332 (3)C9—C101.492 (3)
N2—C81.297 (2)C10—C151.389 (3)
N2—C61.386 (3)C10—C111.392 (3)
N3—C91.367 (3)C11—C121.376 (3)
N3—C81.384 (2)C11—H110.9300
N3—H30.8600C12—C131.363 (3)
C1—C51.386 (3)C12—H120.9300
C1—C21.385 (3)C13—C141.368 (3)
C1—C61.472 (3)C14—C151.379 (3)
C2—C31.384 (3)C14—H140.9300
C2—H20.9300C15—H150.9300
C3—H3A0.9300
C7—S1—C888.21 (10)S1—C7—H7124.3
C3—N1—C4116.14 (18)N2—C8—N3121.11 (17)
C8—N2—C6110.01 (16)N2—C8—S1115.70 (15)
C9—N3—C8123.73 (17)N3—C8—S1123.19 (15)
C9—N3—H3118.1O1—C9—N3121.34 (19)
C8—N3—H3118.1O1—C9—C10121.86 (18)
C5—C1—C2116.68 (19)N3—C9—C10116.72 (17)
C5—C1—C6122.45 (18)C15—C10—C11118.30 (19)
C2—C1—C6120.86 (18)C15—C10—C9123.38 (17)
C3—C2—C1119.31 (19)C11—C10—C9117.99 (18)
C3—C2—H2120.3C12—C11—C10121.1 (2)
C1—C2—H2120.3C12—C11—H11119.5
N1—C3—C2124.19 (19)C10—C11—H11119.5
N1—C3—H3A117.9C13—C12—C11118.4 (2)
C2—C3—H3A117.9C13—C12—H12120.8
N1—C4—C5123.8 (2)C11—C12—H12120.8
N1—C4—H4118.1F1—C13—C12118.1 (2)
C5—C4—H4118.1F1—C13—C14119.0 (2)
C4—C5—C1119.8 (2)C12—C13—C14122.9 (2)
C4—C5—H5120.1C13—C14—C15118.3 (2)
C1—C5—H5120.1C13—C14—H14120.9
C7—C6—N2114.61 (18)C15—C14—H14120.9
C7—C6—C1126.74 (19)C14—C15—C10121.07 (19)
N2—C6—C1118.64 (17)C14—C15—H15119.5
C6—C7—S1111.47 (16)C10—C15—H15119.5
C6—C7—H7124.3
C5—C1—C2—C31.5 (3)C9—N3—C8—S16.6 (3)
C6—C1—C2—C3177.13 (19)C7—S1—C8—N20.23 (17)
C4—N1—C3—C20.0 (3)C7—S1—C8—N3179.79 (17)
C1—C2—C3—N11.0 (3)C8—N3—C9—O18.1 (3)
C3—N1—C4—C50.6 (3)C8—N3—C9—C10168.78 (17)
N1—C4—C5—C10.1 (4)O1—C9—C10—C15160.0 (2)
C2—C1—C5—C41.0 (3)N3—C9—C10—C1516.9 (3)
C6—C1—C5—C4177.60 (19)O1—C9—C10—C1113.3 (3)
C8—N2—C6—C70.0 (2)N3—C9—C10—C11169.80 (18)
C8—N2—C6—C1178.94 (17)C15—C10—C11—C120.2 (3)
C5—C1—C6—C72.7 (3)C9—C10—C11—C12173.4 (2)
C2—C1—C6—C7175.9 (2)C10—C11—C12—C131.2 (4)
C5—C1—C6—N2178.56 (19)C11—C12—C13—F1178.1 (2)
C2—C1—C6—N22.9 (3)C11—C12—C13—C141.9 (4)
N2—C6—C7—S10.2 (2)F1—C13—C14—C15178.81 (19)
C1—C6—C7—S1178.67 (16)C12—C13—C14—C151.2 (4)
C8—S1—C7—C60.21 (16)C13—C14—C15—C100.3 (3)
C6—N2—C8—N3179.84 (17)C11—C10—C15—C140.9 (3)
C6—N2—C8—S10.2 (2)C9—C10—C15—C14172.3 (2)
C9—N3—C8—N2173.43 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N1i0.862.052.873 (2)160
C15—H15···N1i0.932.613.340 (2)136
Symmetry code: (i) x+2, y+1/2, z+3/2.
 

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