Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029806/cv6581sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029806/cv6581Isup2.hkl |
CCDC reference: 287545
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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.
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).
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.
C13H9Cl2N5O2S | F(000) = 752 |
Mr = 370.21 | Dx = 1.594 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb c | Cell parameters from 2652 reflections |
a = 7.3130 (13) Å | θ = 2.6–25.6° |
b = 25.231 (4) Å | µ = 0.57 mm−1 |
c = 8.4269 (15) Å | T = 294 K |
β = 97.217 (3)° | Block, colourless |
V = 1542.5 (5) Å3 | 0.22 × 0.16 × 0.14 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3149 independent reflections |
Radiation source: fine-focus sealed tube | 2155 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→9 |
Tmin = 0.880, Tmax = 0.923 | k = −28→31 |
8564 measured reflections | l = −10→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-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 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C13H9Cl2N5O2S | V = 1542.5 (5) Å3 |
Mr = 370.21 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.3130 (13) Å | µ = 0.57 mm−1 |
b = 25.231 (4) Å | T = 294 K |
c = 8.4269 (15) Å | 0.22 × 0.16 × 0.14 mm |
β = 97.217 (3)° |
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 = 0.923 | Rint = 0.028 |
8564 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.46 e Å−3 |
3149 reflections | Δρmin = −0.35 e Å−3 |
208 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.49983 (10) | 0.31043 (3) | 0.47413 (9) | 0.0475 (2) | |
Cl1 | 0.20912 (12) | 0.46420 (3) | 0.64374 (8) | 0.0635 (3) | |
Cl2 | 0.26195 (13) | 0.51360 (4) | 1.25679 (10) | 0.0725 (3) | |
O1 | 0.8175 (2) | 0.26011 (6) | 0.5168 (2) | 0.0389 (4) | |
O2 | 0.4529 (3) | 0.30945 (7) | 0.8152 (2) | 0.0594 (6) | |
N1 | 0.8287 (3) | 0.33526 (8) | 0.6529 (3) | 0.0418 (5) | |
N2 | 1.0024 (3) | 0.30981 (8) | 0.6816 (2) | 0.0413 (5) | |
N3 | 1.0583 (3) | 0.17445 (8) | 0.6414 (2) | 0.0348 (5) | |
N4 | 1.0617 (3) | 0.16429 (9) | 0.7998 (3) | 0.0489 (6) | |
N5 | 0.9179 (3) | 0.09881 (9) | 0.6516 (3) | 0.0522 (6) | |
C1 | 0.4360 (4) | 0.36590 (10) | 0.5891 (3) | 0.0396 (6) | |
H1A | 0.5251 | 0.3941 | 0.5830 | 0.048* | |
H1B | 0.3170 | 0.3790 | 0.5411 | 0.048* | |
C2 | 0.4249 (3) | 0.35352 (10) | 0.7635 (3) | 0.0389 (6) | |
C3 | 0.3839 (3) | 0.39733 (10) | 0.8748 (3) | 0.0364 (6) | |
C4 | 0.2895 (3) | 0.44484 (10) | 0.8380 (3) | 0.0390 (6) | |
C5 | 0.2521 (4) | 0.48029 (10) | 0.9551 (3) | 0.0437 (6) | |
H5 | 0.1862 | 0.5112 | 0.9279 | 0.052* | |
C6 | 0.3135 (4) | 0.46912 (11) | 1.1113 (3) | 0.0458 (7) | |
C7 | 0.4119 (4) | 0.42401 (12) | 1.1544 (3) | 0.0514 (7) | |
H7 | 0.4563 | 0.4176 | 1.2610 | 0.062* | |
C8 | 0.4439 (4) | 0.38849 (11) | 1.0372 (3) | 0.0458 (7) | |
H8 | 0.5077 | 0.3574 | 1.0669 | 0.055* | |
C9 | 0.7275 (3) | 0.30448 (9) | 0.5574 (3) | 0.0361 (6) | |
C10 | 0.9885 (3) | 0.26711 (10) | 0.6000 (3) | 0.0348 (6) | |
C11 | 1.1267 (3) | 0.22441 (10) | 0.5879 (3) | 0.0406 (6) | |
H11A | 1.1514 | 0.2211 | 0.4779 | 0.049* | |
H11B | 1.2413 | 0.2335 | 0.6532 | 0.049* | |
C12 | 0.9718 (4) | 0.13549 (10) | 0.5575 (3) | 0.0444 (6) | |
H12 | 0.9519 | 0.1343 | 0.4463 | 0.053* | |
C13 | 0.9758 (4) | 0.11856 (12) | 0.7975 (3) | 0.0514 (7) | |
H13 | 0.9561 | 0.1009 | 0.8909 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0437 (4) | 0.0417 (4) | 0.0543 (4) | 0.0074 (3) | −0.0050 (3) | −0.0131 (3) |
Cl1 | 0.0918 (6) | 0.0580 (5) | 0.0394 (4) | 0.0347 (4) | 0.0034 (4) | 0.0054 (3) |
Cl2 | 0.0855 (6) | 0.0830 (6) | 0.0536 (5) | −0.0218 (5) | 0.0263 (4) | −0.0234 (4) |
O1 | 0.0383 (10) | 0.0324 (9) | 0.0449 (10) | 0.0029 (7) | 0.0009 (8) | −0.0085 (8) |
O2 | 0.0743 (14) | 0.0371 (11) | 0.0694 (14) | 0.0104 (10) | 0.0188 (11) | 0.0157 (10) |
N1 | 0.0425 (13) | 0.0385 (12) | 0.0437 (13) | 0.0021 (10) | 0.0032 (10) | −0.0089 (10) |
N2 | 0.0390 (12) | 0.0422 (13) | 0.0420 (12) | −0.0014 (10) | 0.0025 (10) | −0.0083 (10) |
N3 | 0.0355 (11) | 0.0347 (11) | 0.0342 (11) | 0.0045 (9) | 0.0042 (9) | −0.0017 (9) |
N4 | 0.0623 (16) | 0.0490 (14) | 0.0350 (12) | 0.0005 (12) | 0.0040 (11) | 0.0008 (11) |
N5 | 0.0537 (15) | 0.0434 (13) | 0.0576 (15) | −0.0030 (11) | −0.0006 (12) | 0.0032 (12) |
C1 | 0.0385 (14) | 0.0354 (14) | 0.0439 (15) | 0.0066 (11) | 0.0011 (12) | −0.0018 (11) |
C2 | 0.0298 (13) | 0.0358 (14) | 0.0511 (16) | −0.0002 (11) | 0.0055 (11) | 0.0061 (12) |
C3 | 0.0312 (13) | 0.0394 (14) | 0.0390 (14) | −0.0035 (11) | 0.0069 (11) | 0.0087 (11) |
C4 | 0.0410 (15) | 0.0396 (14) | 0.0367 (14) | 0.0010 (11) | 0.0068 (11) | 0.0070 (11) |
C5 | 0.0469 (16) | 0.0418 (15) | 0.0443 (16) | −0.0006 (12) | 0.0135 (13) | 0.0014 (12) |
C6 | 0.0464 (16) | 0.0537 (17) | 0.0394 (15) | −0.0170 (13) | 0.0143 (13) | −0.0052 (13) |
C7 | 0.0515 (17) | 0.066 (2) | 0.0353 (15) | −0.0150 (15) | 0.0007 (13) | 0.0082 (14) |
C8 | 0.0401 (15) | 0.0496 (16) | 0.0470 (16) | −0.0032 (12) | 0.0021 (12) | 0.0160 (13) |
C9 | 0.0420 (14) | 0.0323 (13) | 0.0346 (13) | 0.0028 (11) | 0.0073 (11) | −0.0011 (11) |
C10 | 0.0350 (14) | 0.0357 (14) | 0.0340 (13) | −0.0001 (10) | 0.0050 (11) | 0.0008 (11) |
C11 | 0.0370 (14) | 0.0421 (15) | 0.0432 (14) | 0.0009 (11) | 0.0074 (12) | 0.0001 (12) |
C12 | 0.0490 (16) | 0.0421 (15) | 0.0401 (15) | 0.0006 (12) | −0.0023 (12) | −0.0044 (13) |
C13 | 0.0559 (18) | 0.0528 (18) | 0.0464 (17) | 0.0054 (14) | 0.0098 (14) | 0.0092 (14) |
S1—C9 | 1.730 (3) | C1—H1A | 0.9700 |
S1—C1 | 1.797 (2) | C1—H1B | 0.9700 |
Cl1—C4 | 1.738 (2) | C2—C3 | 1.504 (3) |
Cl2—C6 | 1.738 (3) | C3—C4 | 1.399 (3) |
O1—C9 | 1.364 (3) | C3—C8 | 1.401 (3) |
O1—C10 | 1.366 (3) | C4—C5 | 1.385 (3) |
O2—C2 | 1.202 (3) | C5—C6 | 1.365 (4) |
N1—C9 | 1.284 (3) | C5—H5 | 0.9300 |
N1—N2 | 1.417 (3) | C6—C7 | 1.371 (4) |
N2—C10 | 1.275 (3) | C7—C8 | 1.375 (4) |
N3—C12 | 1.324 (3) | C7—H7 | 0.9300 |
N3—N4 | 1.357 (3) | C8—H8 | 0.9300 |
N3—C11 | 1.449 (3) | C10—C11 | 1.489 (3) |
N4—C13 | 1.313 (4) | C11—H11A | 0.9700 |
N5—C12 | 1.311 (3) | C11—H11B | 0.9700 |
N5—C13 | 1.345 (4) | C12—H12 | 0.9300 |
C1—C2 | 1.515 (4) | C13—H13 | 0.9300 |
C9—S1—C1 | 98.68 (12) | C5—C6—C7 | 121.7 (3) |
C9—O1—C10 | 101.82 (18) | C5—C6—Cl2 | 118.2 (2) |
C9—N1—N2 | 105.47 (19) | C7—C6—Cl2 | 120.1 (2) |
C10—N2—N1 | 106.4 (2) | C6—C7—C8 | 118.8 (3) |
C12—N3—N4 | 109.5 (2) | C6—C7—H7 | 120.6 |
C12—N3—C11 | 129.8 (2) | C8—C7—H7 | 120.6 |
N4—N3—C11 | 120.4 (2) | C7—C8—C3 | 122.5 (3) |
C13—N4—N3 | 101.7 (2) | C7—C8—H8 | 118.8 |
C12—N5—C13 | 102.0 (2) | C3—C8—H8 | 118.8 |
C2—C1—S1 | 114.31 (17) | N1—C9—O1 | 113.3 (2) |
C2—C1—H1A | 108.7 | N1—C9—S1 | 130.63 (19) |
S1—C1—H1A | 108.7 | O1—C9—S1 | 116.08 (17) |
C2—C1—H1B | 108.7 | N2—C10—O1 | 113.1 (2) |
S1—C1—H1B | 108.7 | N2—C10—C11 | 129.7 (2) |
H1A—C1—H1B | 107.6 | O1—C10—C11 | 117.2 (2) |
O2—C2—C3 | 119.5 (2) | N3—C11—C10 | 110.1 (2) |
O2—C2—C1 | 121.0 (2) | N3—C11—H11A | 109.6 |
C3—C2—C1 | 119.5 (2) | C10—C11—H11A | 109.6 |
C4—C3—C8 | 116.0 (2) | N3—C11—H11B | 109.6 |
C4—C3—C2 | 128.5 (2) | C10—C11—H11B | 109.6 |
C8—C3—C2 | 115.4 (2) | H11A—C11—H11B | 108.1 |
C5—C4—C3 | 122.1 (2) | N5—C12—N3 | 111.2 (2) |
C5—C4—Cl1 | 114.6 (2) | N5—C12—H12 | 124.4 |
C3—C4—Cl1 | 123.3 (2) | N3—C12—H12 | 124.4 |
C6—C5—C4 | 118.9 (3) | N4—C13—N5 | 115.7 (2) |
C6—C5—H5 | 120.5 | N4—C13—H13 | 122.1 |
C4—C5—H5 | 120.5 | N5—C13—H13 | 122.1 |
C9—N1—N2—C10 | 0.7 (3) | C4—C3—C8—C7 | 0.2 (4) |
C12—N3—N4—C13 | 0.5 (3) | C2—C3—C8—C7 | −178.0 (2) |
C11—N3—N4—C13 | 174.8 (2) | N2—N1—C9—O1 | −0.5 (3) |
C9—S1—C1—C2 | −70.0 (2) | N2—N1—C9—S1 | 179.50 (19) |
S1—C1—C2—O2 | −1.8 (3) | C10—O1—C9—N1 | 0.2 (3) |
S1—C1—C2—C3 | 176.37 (18) | C10—O1—C9—S1 | −179.86 (16) |
O2—C2—C3—C4 | −156.2 (3) | C1—S1—C9—N1 | −10.0 (3) |
C1—C2—C3—C4 | 25.6 (4) | C1—S1—C9—O1 | 170.03 (18) |
O2—C2—C3—C8 | 21.7 (3) | N1—N2—C10—O1 | −0.6 (3) |
C1—C2—C3—C8 | −156.5 (2) | N1—N2—C10—C11 | −178.3 (2) |
C8—C3—C4—C5 | −2.0 (4) | C9—O1—C10—N2 | 0.3 (3) |
C2—C3—C4—C5 | 176.0 (2) | C9—O1—C10—C11 | 178.3 (2) |
C8—C3—C4—Cl1 | 178.23 (19) | C12—N3—C11—C10 | 95.6 (3) |
C2—C3—C4—Cl1 | −3.8 (4) | N4—N3—C11—C10 | −77.4 (3) |
C3—C4—C5—C6 | 1.7 (4) | N2—C10—C11—N3 | 119.4 (3) |
Cl1—C4—C5—C6 | −178.5 (2) | O1—C10—C11—N3 | −58.2 (3) |
C4—C5—C6—C7 | 0.5 (4) | C13—N5—C12—N3 | 0.7 (3) |
C4—C5—C6—Cl2 | −179.00 (19) | N4—N3—C12—N5 | −0.8 (3) |
C5—C6—C7—C8 | −2.1 (4) | C11—N3—C12—N5 | −174.4 (2) |
Cl2—C6—C7—C8 | 177.3 (2) | N3—N4—C13—N5 | −0.1 (3) |
C6—C7—C8—C3 | 1.8 (4) | C12—N5—C13—N4 | −0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N5i | 0.93 | 2.41 | 3.319 (4) | 167 |
C1—H1B···Cl1 | 0.97 | 2.48 | 3.051 (2) | 117 |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C13H9Cl2N5O2S |
Mr | 370.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 7.3130 (13), 25.231 (4), 8.4269 (15) |
β (°) | 97.217 (3) |
V (Å3) | 1542.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.22 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.880, 0.923 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8564, 3149, 2155 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.097, 1.02 |
No. of reflections | 3149 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.35 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
S1—C9 | 1.730 (3) | N1—C9 | 1.284 (3) |
S1—C1 | 1.797 (2) | N1—N2 | 1.417 (3) |
O1—C9 | 1.364 (3) | N2—C10 | 1.275 (3) |
O1—C10 | 1.366 (3) | ||
C9—S1—C1 | 98.68 (12) | C9—O1—C10 | 101.82 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N5i | 0.93 | 2.41 | 3.319 (4) | 167.2 |
C1—H1B···Cl1 | 0.97 | 2.48 | 3.051 (2) | 117.2 |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
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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 π–π stacking interaction. The crystal packing (Fig. 2) is mainly stabilized by van der Waals forces.