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In the mol­ecule of the title compound, C13H9Cl2N5O2S, prepared by the reaction of 5-[(1H-1,2,4-triazol-1-yl)meth­yl]-1,3,4-oxadiazole-2-thiol and 2-bromo-1-(2,4-dichloro­phen­yl)ethanone, the 1,3,4-oxadiazole ring makes dihedral angles of 50.56 (2) and 82.95 (4)°, respectively, with the benzene and triazole rings. Weak inter­molecular C—H...N hydrogen bonds link the mol­ecules into zigzag chains extending along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029806/cv6581sup1.cif
Contains datablocks 50128B, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029806/cv6581Isup2.hkl
Contains datablock I

CCDC reference: 287545

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.097
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 1 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

Comment top

The triazole and 1,3,4-oxadiazole derivatives are known to possess a wide spectrum of insecticidal and fungicidal activities (Pachhamia & Parikh, 1988; Xu et al., 2002). In our search for compounds with better properties, the title compound, (I) (Fig. 1), has been synthesized. We report here its crystal structure.

In (I), the bond lengths and angles of the triazole and 1,3,4-oxadiazole rings (Table 1) are in a good agreement with the values quoted in previous reports (Xu et al., 2005; Zhang et al., 2002). Atoms C11 and S1 lie in the plane of the 1,3,4-oxadiazole ring (C9/C10/N1/N2/O1). The dihedral angles formed by the benzene (C3–C8/Cl1/Cl2) and triazole (C12/C13/N3–N5) rings with 1,3,4-oxadiazole ring are 50.56 (2) and 82.95 (4)°, respectively. Weak intermolecular C—H···N hydrogen bonds (Table 2) link the molecules into zigzag chains extending along the b axis. The relatively short distance Cg1···Cg2ii of 3.702 (2) Å, where Cg1 and Cg2 denote the centroids of the triazole and benzene rings, respectively [symmetry code: (ii) 1 + x, 1/2 − y, −1/2 + z], indicates a possible ππ stacking interaction. The crystal packing (Fig. 2) is mainly stabilized by van der Waals forces.

Experimental top

A mixture of 5-[(1H-1,2,4-triazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol (0.02 mol) and 2-bromo-1-(2,4-dichlorophenyl)ethanone (0.02 mol) was stirred in refluxing acetone (15 ml) for 5 h at 327 K to afford the title compound (5.90 g, yield 80%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å, and included in the final cycles of refinement using a riding model, 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); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 40% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound, viewed down the c axis. Hydrogen bonds are shown as dashed lines.
2-(5-((1H-1,2,4-triazol-1-yl)methyl)-1,3,4-oxadiazol-2-ylthio)-1 -(2,4-dichlorophenyl)ethanone top
Crystal data top
C13H9Cl2N5O2SF(000) = 752
Mr = 370.21Dx = 1.594 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb cCell parameters from 2652 reflections
a = 7.3130 (13) Åθ = 2.6–25.6°
b = 25.231 (4) ŵ = 0.57 mm1
c = 8.4269 (15) ÅT = 294 K
β = 97.217 (3)°Block, colourless
V = 1542.5 (5) Å30.22 × 0.16 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3149 independent reflections
Radiation source: fine-focus sealed tube2155 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 79
Tmin = 0.880, Tmax = 0.923k = 2831
8564 measured reflectionsl = 1010
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0334P)2 + 0.996P]
where P = (Fo2 + 2Fc2)/3
3149 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C13H9Cl2N5O2SV = 1542.5 (5) Å3
Mr = 370.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.3130 (13) ŵ = 0.57 mm1
b = 25.231 (4) ÅT = 294 K
c = 8.4269 (15) Å0.22 × 0.16 × 0.14 mm
β = 97.217 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3149 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2155 reflections with I > 2σ(I)
Tmin = 0.880, Tmax = 0.923Rint = 0.028
8564 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.02Δρmax = 0.46 e Å3
3149 reflectionsΔρmin = 0.35 e Å3
208 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
S10.49983 (10)0.31043 (3)0.47413 (9)0.0475 (2)
Cl10.20912 (12)0.46420 (3)0.64374 (8)0.0635 (3)
Cl20.26195 (13)0.51360 (4)1.25679 (10)0.0725 (3)
O10.8175 (2)0.26011 (6)0.5168 (2)0.0389 (4)
O20.4529 (3)0.30945 (7)0.8152 (2)0.0594 (6)
N10.8287 (3)0.33526 (8)0.6529 (3)0.0418 (5)
N21.0024 (3)0.30981 (8)0.6816 (2)0.0413 (5)
N31.0583 (3)0.17445 (8)0.6414 (2)0.0348 (5)
N41.0617 (3)0.16429 (9)0.7998 (3)0.0489 (6)
N50.9179 (3)0.09881 (9)0.6516 (3)0.0522 (6)
C10.4360 (4)0.36590 (10)0.5891 (3)0.0396 (6)
H1A0.52510.39410.58300.048*
H1B0.31700.37900.54110.048*
C20.4249 (3)0.35352 (10)0.7635 (3)0.0389 (6)
C30.3839 (3)0.39733 (10)0.8748 (3)0.0364 (6)
C40.2895 (3)0.44484 (10)0.8380 (3)0.0390 (6)
C50.2521 (4)0.48029 (10)0.9551 (3)0.0437 (6)
H50.18620.51120.92790.052*
C60.3135 (4)0.46912 (11)1.1113 (3)0.0458 (7)
C70.4119 (4)0.42401 (12)1.1544 (3)0.0514 (7)
H70.45630.41761.26100.062*
C80.4439 (4)0.38849 (11)1.0372 (3)0.0458 (7)
H80.50770.35741.06690.055*
C90.7275 (3)0.30448 (9)0.5574 (3)0.0361 (6)
C100.9885 (3)0.26711 (10)0.6000 (3)0.0348 (6)
C111.1267 (3)0.22441 (10)0.5879 (3)0.0406 (6)
H11A1.15140.22110.47790.049*
H11B1.24130.23350.65320.049*
C120.9718 (4)0.13549 (10)0.5575 (3)0.0444 (6)
H120.95190.13430.44630.053*
C130.9758 (4)0.11856 (12)0.7975 (3)0.0514 (7)
H130.95610.10090.89090.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0437 (4)0.0417 (4)0.0543 (4)0.0074 (3)0.0050 (3)0.0131 (3)
Cl10.0918 (6)0.0580 (5)0.0394 (4)0.0347 (4)0.0034 (4)0.0054 (3)
Cl20.0855 (6)0.0830 (6)0.0536 (5)0.0218 (5)0.0263 (4)0.0234 (4)
O10.0383 (10)0.0324 (9)0.0449 (10)0.0029 (7)0.0009 (8)0.0085 (8)
O20.0743 (14)0.0371 (11)0.0694 (14)0.0104 (10)0.0188 (11)0.0157 (10)
N10.0425 (13)0.0385 (12)0.0437 (13)0.0021 (10)0.0032 (10)0.0089 (10)
N20.0390 (12)0.0422 (13)0.0420 (12)0.0014 (10)0.0025 (10)0.0083 (10)
N30.0355 (11)0.0347 (11)0.0342 (11)0.0045 (9)0.0042 (9)0.0017 (9)
N40.0623 (16)0.0490 (14)0.0350 (12)0.0005 (12)0.0040 (11)0.0008 (11)
N50.0537 (15)0.0434 (13)0.0576 (15)0.0030 (11)0.0006 (12)0.0032 (12)
C10.0385 (14)0.0354 (14)0.0439 (15)0.0066 (11)0.0011 (12)0.0018 (11)
C20.0298 (13)0.0358 (14)0.0511 (16)0.0002 (11)0.0055 (11)0.0061 (12)
C30.0312 (13)0.0394 (14)0.0390 (14)0.0035 (11)0.0069 (11)0.0087 (11)
C40.0410 (15)0.0396 (14)0.0367 (14)0.0010 (11)0.0068 (11)0.0070 (11)
C50.0469 (16)0.0418 (15)0.0443 (16)0.0006 (12)0.0135 (13)0.0014 (12)
C60.0464 (16)0.0537 (17)0.0394 (15)0.0170 (13)0.0143 (13)0.0052 (13)
C70.0515 (17)0.066 (2)0.0353 (15)0.0150 (15)0.0007 (13)0.0082 (14)
C80.0401 (15)0.0496 (16)0.0470 (16)0.0032 (12)0.0021 (12)0.0160 (13)
C90.0420 (14)0.0323 (13)0.0346 (13)0.0028 (11)0.0073 (11)0.0011 (11)
C100.0350 (14)0.0357 (14)0.0340 (13)0.0001 (10)0.0050 (11)0.0008 (11)
C110.0370 (14)0.0421 (15)0.0432 (14)0.0009 (11)0.0074 (12)0.0001 (12)
C120.0490 (16)0.0421 (15)0.0401 (15)0.0006 (12)0.0023 (12)0.0044 (13)
C130.0559 (18)0.0528 (18)0.0464 (17)0.0054 (14)0.0098 (14)0.0092 (14)
Geometric parameters (Å, º) top
S1—C91.730 (3)C1—H1A0.9700
S1—C11.797 (2)C1—H1B0.9700
Cl1—C41.738 (2)C2—C31.504 (3)
Cl2—C61.738 (3)C3—C41.399 (3)
O1—C91.364 (3)C3—C81.401 (3)
O1—C101.366 (3)C4—C51.385 (3)
O2—C21.202 (3)C5—C61.365 (4)
N1—C91.284 (3)C5—H50.9300
N1—N21.417 (3)C6—C71.371 (4)
N2—C101.275 (3)C7—C81.375 (4)
N3—C121.324 (3)C7—H70.9300
N3—N41.357 (3)C8—H80.9300
N3—C111.449 (3)C10—C111.489 (3)
N4—C131.313 (4)C11—H11A0.9700
N5—C121.311 (3)C11—H11B0.9700
N5—C131.345 (4)C12—H120.9300
C1—C21.515 (4)C13—H130.9300
C9—S1—C198.68 (12)C5—C6—C7121.7 (3)
C9—O1—C10101.82 (18)C5—C6—Cl2118.2 (2)
C9—N1—N2105.47 (19)C7—C6—Cl2120.1 (2)
C10—N2—N1106.4 (2)C6—C7—C8118.8 (3)
C12—N3—N4109.5 (2)C6—C7—H7120.6
C12—N3—C11129.8 (2)C8—C7—H7120.6
N4—N3—C11120.4 (2)C7—C8—C3122.5 (3)
C13—N4—N3101.7 (2)C7—C8—H8118.8
C12—N5—C13102.0 (2)C3—C8—H8118.8
C2—C1—S1114.31 (17)N1—C9—O1113.3 (2)
C2—C1—H1A108.7N1—C9—S1130.63 (19)
S1—C1—H1A108.7O1—C9—S1116.08 (17)
C2—C1—H1B108.7N2—C10—O1113.1 (2)
S1—C1—H1B108.7N2—C10—C11129.7 (2)
H1A—C1—H1B107.6O1—C10—C11117.2 (2)
O2—C2—C3119.5 (2)N3—C11—C10110.1 (2)
O2—C2—C1121.0 (2)N3—C11—H11A109.6
C3—C2—C1119.5 (2)C10—C11—H11A109.6
C4—C3—C8116.0 (2)N3—C11—H11B109.6
C4—C3—C2128.5 (2)C10—C11—H11B109.6
C8—C3—C2115.4 (2)H11A—C11—H11B108.1
C5—C4—C3122.1 (2)N5—C12—N3111.2 (2)
C5—C4—Cl1114.6 (2)N5—C12—H12124.4
C3—C4—Cl1123.3 (2)N3—C12—H12124.4
C6—C5—C4118.9 (3)N4—C13—N5115.7 (2)
C6—C5—H5120.5N4—C13—H13122.1
C4—C5—H5120.5N5—C13—H13122.1
C9—N1—N2—C100.7 (3)C4—C3—C8—C70.2 (4)
C12—N3—N4—C130.5 (3)C2—C3—C8—C7178.0 (2)
C11—N3—N4—C13174.8 (2)N2—N1—C9—O10.5 (3)
C9—S1—C1—C270.0 (2)N2—N1—C9—S1179.50 (19)
S1—C1—C2—O21.8 (3)C10—O1—C9—N10.2 (3)
S1—C1—C2—C3176.37 (18)C10—O1—C9—S1179.86 (16)
O2—C2—C3—C4156.2 (3)C1—S1—C9—N110.0 (3)
C1—C2—C3—C425.6 (4)C1—S1—C9—O1170.03 (18)
O2—C2—C3—C821.7 (3)N1—N2—C10—O10.6 (3)
C1—C2—C3—C8156.5 (2)N1—N2—C10—C11178.3 (2)
C8—C3—C4—C52.0 (4)C9—O1—C10—N20.3 (3)
C2—C3—C4—C5176.0 (2)C9—O1—C10—C11178.3 (2)
C8—C3—C4—Cl1178.23 (19)C12—N3—C11—C1095.6 (3)
C2—C3—C4—Cl13.8 (4)N4—N3—C11—C1077.4 (3)
C3—C4—C5—C61.7 (4)N2—C10—C11—N3119.4 (3)
Cl1—C4—C5—C6178.5 (2)O1—C10—C11—N358.2 (3)
C4—C5—C6—C70.5 (4)C13—N5—C12—N30.7 (3)
C4—C5—C6—Cl2179.00 (19)N4—N3—C12—N50.8 (3)
C5—C6—C7—C82.1 (4)C11—N3—C12—N5174.4 (2)
Cl2—C6—C7—C8177.3 (2)N3—N4—C13—N50.1 (3)
C6—C7—C8—C31.8 (4)C12—N5—C13—N40.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···N5i0.932.413.319 (4)167
C1—H1B···Cl10.972.483.051 (2)117
Symmetry code: (i) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC13H9Cl2N5O2S
Mr370.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)7.3130 (13), 25.231 (4), 8.4269 (15)
β (°) 97.217 (3)
V3)1542.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.57
Crystal size (mm)0.22 × 0.16 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.880, 0.923
No. of measured, independent and
observed [I > 2σ(I)] reflections
8564, 3149, 2155
Rint0.028
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.097, 1.02
No. of reflections3149
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.35

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

Selected geometric parameters (Å, º) top
S1—C91.730 (3)N1—C91.284 (3)
S1—C11.797 (2)N1—N21.417 (3)
O1—C91.364 (3)N2—C101.275 (3)
O1—C101.366 (3)
C9—S1—C198.68 (12)C9—O1—C10101.82 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···N5i0.932.413.319 (4)167.2
C1—H1B···Cl10.972.483.051 (2)117.2
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

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