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The title compound, C19H12ClN5O2S, has been synthesized as a potential fungicidal agent. The dihedral angle between the thia­zole and triazole rings is 38.5 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042212/dn6288sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042212/dn6288Isup2.hkl
Contains datablock I

CCDC reference: 296559

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.126
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.26 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Comment top

Thiazole derivatives are reported to exhibit diverse biological activities, such as antituberculous, bacteriostatic and fungistatic activities (Smia et al., 2000). In search of novel thiazole compounds with potent fungicidal activities, we have sought to synthesize such 2-aminothiazole compounds containing 1H-1,2,4-triazole units. We report here the crystal structure of the title compound, (I).

The molecular structure of (I) contains four planar subunits, namely a thiazole ring, a triazole ring, a 4-chlorophenyl ring and a methylbenzo[1,2-d]-1,3-dioxolyl ring. The methylbenzo[1,2-d]-1,3-dioxolyl and thiazole rings are nearly planar, with a dihedral angle between them of 3.0 (1)°, whereas the triazole and 4-chlorophenyl rings are twisted with respect to the thiazole by 38.5 (1) and 36.0 (1)°, respectively.

The occurrence of weak C—H···O interactions (Table 1) results in the formation of pseudo-dimers arranged around an inversion centre.

Experimental top

2-Amino-4-(4-chlorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole (0.42 g, 1.5 mmol) and heliotropin (0.22 g, 1.5 mmol) were mixed in benzene (20 ml). Three drops of piperidine were added to the mixed solution. The solution was then heated and refluxed in a 50 ml flask equipped with a Dean–Stark trap condenser until no water appeared (5 h). Concentration of the reaction solution and chromatography on a silica-gel column using ethyl acetate–petroleum ether (1:3) as eluent gave the title compound (0.51 g, yield 83.2%). Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation from ethanol.

Refinement top

All H atoms were placed in calculated positions and treated as riding on their parent C atoms, with C—H = 0.93 Å (Caromatic) and C—H = 0.97 Å (Cmethylene), and with Uiso(H) = 1.2Ueq(C).

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) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A molecular view of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view showing the formation of pseudo-dimers through weak C—H···O interactions (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity.
(E)-4-(4-Chlorophenyl)-N-(5-methyl-1,3-benzodioxol-5-ylmethylene)- 5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine top
Crystal data top
C19H12ClN5O2SZ = 2
Mr = 409.85F(000) = 420
Triclinic, P1Dx = 1.512 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 7.8260 (19) ÅCell parameters from 1873 reflections
b = 8.929 (2) Åθ = 2.9–26.3°
c = 14.221 (3) ŵ = 0.36 mm1
α = 94.871 (4)°T = 294 K
β = 92.332 (4)°Block, yellow
γ = 114.170 (4)°0.26 × 0.20 × 0.16 mm
V = 900.2 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3160 independent reflections
Radiation source: fine-focus sealed tube2302 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.910, Tmax = 0.945k = 109
4582 measured reflectionsl = 1516
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0622P)2 + 0.3304P]
where P = (Fo2 + 2Fc2)/3
3160 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
C19H12ClN5O2Sγ = 114.170 (4)°
Mr = 409.85V = 900.2 (4) Å3
Triclinic, P1Z = 2
a = 7.8260 (19) ÅMo Kα radiation
b = 8.929 (2) ŵ = 0.36 mm1
c = 14.221 (3) ÅT = 294 K
α = 94.871 (4)°0.26 × 0.20 × 0.16 mm
β = 92.332 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3160 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2302 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.945Rint = 0.029
4582 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.01Δρmax = 0.32 e Å3
3160 reflectionsΔρmin = 0.41 e Å3
253 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
S11.26020 (9)0.46507 (8)0.50351 (5)0.0461 (2)
Cl10.66432 (13)0.29773 (17)0.03482 (6)0.1048 (4)
O10.6359 (3)0.2717 (2)0.87759 (13)0.0562 (5)
O20.9087 (3)0.0324 (2)0.90043 (13)0.0552 (5)
N11.3546 (3)0.6178 (2)0.34565 (15)0.0415 (5)
N21.4619 (3)0.7640 (3)0.39798 (16)0.0554 (6)
N31.5589 (4)0.7588 (3)0.25117 (18)0.0631 (7)
N40.9525 (3)0.2587 (2)0.41150 (14)0.0405 (5)
N51.0020 (3)0.2142 (3)0.57465 (14)0.0449 (5)
C11.0451 (3)0.3735 (3)0.35029 (17)0.0371 (6)
C20.9531 (3)0.3571 (3)0.25549 (18)0.0400 (6)
C30.8440 (4)0.2022 (3)0.20817 (19)0.0467 (7)
H30.83100.10860.23670.056*
C40.7545 (4)0.1842 (4)0.1200 (2)0.0577 (8)
H40.68150.07940.08930.069*
C50.7739 (4)0.3220 (5)0.0777 (2)0.0638 (9)
C60.8768 (5)0.4763 (5)0.1230 (2)0.0747 (10)
H60.88700.56890.09410.090*
C70.9662 (4)0.4948 (4)0.2119 (2)0.0608 (8)
H71.03560.60010.24280.073*
C81.2142 (3)0.4906 (3)0.38863 (17)0.0397 (6)
C91.4181 (4)0.6178 (3)0.2594 (2)0.0566 (8)
H91.36880.52960.21190.068*
C101.5792 (4)0.8412 (4)0.3368 (2)0.0654 (9)
H101.67160.94780.35220.078*
C111.0482 (3)0.2945 (3)0.49322 (17)0.0391 (6)
C120.8471 (4)0.0866 (3)0.57139 (18)0.0446 (6)
H120.76950.05180.51530.054*
C130.7873 (4)0.0064 (3)0.65205 (17)0.0410 (6)
C140.8979 (4)0.0432 (3)0.73899 (18)0.0415 (6)
H141.01100.13680.74760.050*
C150.8307 (4)0.0528 (3)0.80944 (17)0.0408 (6)
C160.6653 (4)0.1945 (3)0.79674 (17)0.0417 (6)
C170.5543 (4)0.2444 (3)0.71386 (19)0.0486 (7)
H170.44180.33870.70640.058*
C180.6187 (4)0.1462 (3)0.64105 (18)0.0476 (7)
H180.54690.17510.58330.057*
C190.7965 (4)0.1776 (4)0.9421 (2)0.0573 (8)
H19A0.86820.24190.95350.069*
H19B0.75770.14771.00210.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0435 (4)0.0462 (4)0.0375 (4)0.0076 (3)0.0024 (3)0.0073 (3)
Cl10.0629 (6)0.1850 (12)0.0413 (5)0.0219 (6)0.0027 (4)0.0368 (6)
O10.0551 (12)0.0602 (12)0.0384 (11)0.0068 (10)0.0026 (9)0.0171 (9)
O20.0583 (12)0.0564 (12)0.0352 (10)0.0083 (10)0.0086 (8)0.0095 (9)
N10.0417 (12)0.0356 (11)0.0378 (12)0.0064 (9)0.0009 (9)0.0067 (9)
N20.0574 (15)0.0413 (13)0.0444 (13)0.0023 (11)0.0003 (11)0.0037 (10)
N30.0642 (16)0.0578 (15)0.0472 (15)0.0029 (13)0.0081 (12)0.0154 (12)
N40.0393 (11)0.0403 (12)0.0372 (12)0.0111 (9)0.0016 (9)0.0088 (9)
N50.0473 (13)0.0468 (13)0.0371 (12)0.0146 (11)0.0035 (10)0.0121 (10)
C10.0374 (13)0.0357 (13)0.0372 (14)0.0132 (11)0.0034 (10)0.0094 (11)
C20.0342 (13)0.0434 (14)0.0388 (14)0.0112 (11)0.0030 (11)0.0104 (11)
C30.0418 (15)0.0513 (16)0.0430 (16)0.0147 (12)0.0038 (12)0.0072 (13)
C40.0438 (16)0.072 (2)0.0447 (17)0.0142 (15)0.0007 (13)0.0037 (15)
C50.0389 (16)0.104 (3)0.0369 (16)0.0162 (17)0.0034 (12)0.0208 (17)
C60.061 (2)0.084 (2)0.068 (2)0.0135 (18)0.0051 (17)0.0441 (19)
C70.0595 (18)0.0504 (17)0.0604 (19)0.0091 (14)0.0096 (15)0.0207 (15)
C80.0425 (14)0.0368 (13)0.0361 (14)0.0122 (11)0.0027 (11)0.0066 (11)
C90.0624 (19)0.0473 (16)0.0419 (16)0.0044 (14)0.0076 (13)0.0044 (13)
C100.0628 (19)0.0509 (17)0.0515 (19)0.0079 (15)0.0005 (15)0.0100 (15)
C110.0415 (14)0.0383 (13)0.0357 (14)0.0139 (11)0.0040 (11)0.0083 (11)
C120.0497 (16)0.0466 (15)0.0336 (14)0.0159 (13)0.0006 (11)0.0073 (11)
C130.0446 (14)0.0406 (14)0.0362 (14)0.0154 (12)0.0030 (11)0.0078 (11)
C140.0404 (14)0.0360 (13)0.0413 (15)0.0091 (11)0.0014 (11)0.0058 (11)
C150.0439 (14)0.0425 (14)0.0331 (14)0.0159 (12)0.0019 (11)0.0017 (11)
C160.0437 (14)0.0446 (14)0.0340 (14)0.0146 (12)0.0059 (11)0.0078 (11)
C170.0404 (14)0.0465 (15)0.0442 (16)0.0031 (12)0.0006 (12)0.0085 (12)
C180.0471 (15)0.0524 (16)0.0337 (14)0.0112 (13)0.0036 (11)0.0065 (12)
C190.0542 (17)0.0647 (19)0.0412 (16)0.0108 (15)0.0023 (13)0.0169 (14)
Geometric parameters (Å, º) top
S1—C81.713 (3)C3—H30.9300
S1—C111.722 (3)C4—C51.371 (5)
Cl1—C51.738 (3)C4—H40.9300
O1—C161.370 (3)C5—C61.364 (5)
O1—C191.427 (3)C6—C71.383 (4)
O2—C151.373 (3)C6—H60.9300
O2—C191.429 (3)C7—H70.9300
N1—C91.342 (3)C9—H90.9300
N1—N21.360 (3)C10—H100.9300
N1—C81.421 (3)C12—C131.453 (4)
N2—C101.312 (4)C12—H120.9300
N3—C91.309 (3)C13—C181.387 (4)
N3—C101.336 (4)C13—C141.407 (3)
N4—C111.298 (3)C14—C151.354 (4)
N4—C11.389 (3)C14—H140.9300
N5—C121.275 (3)C15—C161.382 (4)
N5—C111.396 (3)C16—C171.361 (4)
C1—C81.362 (3)C17—C181.389 (4)
C1—C21.469 (3)C17—H170.9300
C2—C31.387 (4)C18—H180.9300
C2—C71.393 (4)C19—H19A0.9700
C3—C41.375 (4)C19—H19B0.9700
C8—S1—C1188.10 (12)N3—C9—H9124.6
C16—O1—C19106.1 (2)N1—C9—H9124.6
C15—O2—C19106.3 (2)N2—C10—N3116.6 (3)
C9—N1—N2109.1 (2)N2—C10—H10121.7
C9—N1—C8131.0 (2)N3—C10—H10121.7
N2—N1—C8119.6 (2)N4—C11—N5128.8 (2)
C10—N2—N1101.3 (2)N4—C11—S1115.96 (19)
C9—N3—C10102.1 (2)N5—C11—S1115.28 (18)
C11—N4—C1110.7 (2)N5—C12—C13122.4 (2)
C12—N5—C11118.3 (2)N5—C12—H12118.8
C8—C1—N4113.4 (2)C13—C12—H12118.8
C8—C1—C2128.3 (2)C18—C13—C14120.7 (2)
N4—C1—C2118.3 (2)C18—C13—C12118.3 (2)
C3—C2—C7117.9 (3)C14—C13—C12120.9 (2)
C3—C2—C1120.5 (2)C15—C14—C13116.4 (2)
C7—C2—C1121.6 (2)C15—C14—H14121.8
C4—C3—C2121.4 (3)C13—C14—H14121.8
C4—C3—H3119.3C14—C15—O2128.4 (2)
C2—C3—H3119.3C14—C15—C16122.3 (2)
C5—C4—C3119.5 (3)O2—C15—C16109.3 (2)
C5—C4—H4120.3C17—C16—O1127.4 (2)
C3—C4—H4120.3C17—C16—C15122.6 (2)
C6—C5—C4120.8 (3)O1—C16—C15110.1 (2)
C6—C5—Cl1120.2 (3)C16—C17—C18116.1 (2)
C4—C5—Cl1119.0 (3)C16—C17—H17122.0
C5—C6—C7119.9 (3)C18—C17—H17122.0
C5—C6—H6120.1C13—C18—C17121.9 (2)
C7—C6—H6120.1C13—C18—H18119.1
C6—C7—C2120.6 (3)C17—C18—H18119.1
C6—C7—H7119.7O1—C19—O2107.6 (2)
C2—C7—H7119.7O1—C19—H19A110.2
C1—C8—N1129.6 (2)O2—C19—H19A110.2
C1—C8—S1111.83 (19)O1—C19—H19B110.2
N1—C8—S1118.47 (18)O2—C19—H19B110.2
N3—C9—N1110.8 (2)H19A—C19—H19B108.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O1i0.932.523.371 (4)152
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC19H12ClN5O2S
Mr409.85
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)7.8260 (19), 8.929 (2), 14.221 (3)
α, β, γ (°)94.871 (4), 92.332 (4), 114.170 (4)
V3)900.2 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.26 × 0.20 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.910, 0.945
No. of measured, independent and
observed [I > 2σ(I)] reflections
4582, 3160, 2302
Rint0.029
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.127, 1.01
No. of reflections3160
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.41

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999) and PLATON (Spek, 2003), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O1i0.932.523.371 (4)152.2
Symmetry code: (i) x+2, y, z+1.
 

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