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In the title compound, C13H12N4OS2, the central oxadiazole ring makes dihedral angles of 8.9 (2) and 89.6 (3)° with the benzene and thia­diazole rings, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054682/hb2618sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054682/hb2618Isup2.hkl
Contains datablock I

CCDC reference: 674079

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.062
  • wR factor = 0.178
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C2 .. 5.49 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C13
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

1,2,4-Oxadiazoles represent an important class of five-membered heterocycles with medicinal applications such as anti-inflammatory (Nicolaides et al., 1998) and antipicornaviral (Romero, 2001) properties. We are focusing our synthetic and structural studies on new oxindole derivatives. Sulfurether derivatives exhibited strong inhibiting activity to Staphylococcus aureus (Talar & Dejai, 1996). We report here the structure of the title compound, (I), containing a thiadiazole sulfanylether group.

There are three rings in the molecule. The benezene and oxadiazole ring are close to coplanar due to the extended aromatic system [dihedral angle = 8.9 (2)°]. The angle between the oxadiazole plane and the thiadiazole moiety is 89.6 (3)°. The molecular structure of (I) is shown in Fig. 1.

Related literature top

For related literature, see: Nicolaides et al. (1998); Romero (2001); Talar & Dejai (1996).

Experimental top

5-Mercapto-2-methyl-1,3,4-thiadiazole (20 mmol) was dissolved in ethanol (70 ml) and water (70 mmol). Sodium acetate (20 mmol) was added to this mixture. Then 3-[2-(methyl)phenyl]-5-chloromethyl-1,2,4-oxadiazol (40 mmol) was added. The resulting mixture was refluxed for 8 h. After cooling and filtrating, the crude title compound was obtained. Pure compound (I) was obstained by crystallizing from a mixture of ethyl acetate (8 ml) and petrolum ether (bp. 333–363 K) (4 ml). Colourless blocks of (I) were obstained by slow evaporation of an ethanol solution. 1H NMR (CDCl3, δ, p.p.m.): 7.35–7.36 (m, 1H), 7.10–7.13(m, 3H), 4.18–4.19 (s, 2H), 2.38–2.39 (s,3H), 2.32–2.33 (s,3H).

Refinement top

The H atoms were placed geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level (H atoms represented by arbitrary spheres).
2-Methyl-5-[3-(2-methylphenyl)-1,2,4-oxadiazol-5-ylmethylsulfanyl]- 1,3,4-thiadiazole top
Crystal data top
C13H12N4OS2F(000) = 632
Mr = 304.39Dx = 1.449 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.309 (2) Åθ = 9–13°
b = 12.992 (3) ŵ = 0.38 mm1
c = 10.600 (2) ÅT = 293 K
β = 100.63 (3)°Block, colourless
V = 1395.3 (5) Å30.30 × 0.10 × 0.10 mm
Z = 4
Data collection top
Nonius CAD-4
diffractometer
1694 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
ω/2θ scansh = 1212
Absorption correction: ψ scan
(North et al., 1968)
k = 016
Tmin = 0.894, Tmax = 0.963l = 013
2890 measured reflections3 standard reflections every 200 reflections
2737 independent reflections intensity decay: none
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.060P)2 + 2.3P]
where P = (Fo2 + 2Fc2)/3
2737 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C13H12N4OS2V = 1395.3 (5) Å3
Mr = 304.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.309 (2) ŵ = 0.38 mm1
b = 12.992 (3) ÅT = 293 K
c = 10.600 (2) Å0.30 × 0.10 × 0.10 mm
β = 100.63 (3)°
Data collection top
Nonius CAD-4
diffractometer
1694 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.032
Tmin = 0.894, Tmax = 0.9633 standard reflections every 200 reflections
2890 measured reflections intensity decay: none
2737 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
2737 reflectionsΔρmin = 0.35 e Å3
181 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
O0.1434 (4)0.1828 (2)0.0705 (3)0.0684 (10)
S10.53469 (12)0.38060 (11)0.12681 (13)0.0669 (4)
N10.2889 (4)0.3910 (3)0.0430 (4)0.0695 (12)
C10.4913 (6)0.5355 (4)0.3034 (5)0.0754 (15)
H1B0.42090.57700.32390.113*
H1C0.55820.57930.28040.113*
H1D0.52860.49470.37660.113*
S20.39670 (13)0.24762 (10)0.09151 (13)0.0618 (4)
N20.3157 (4)0.4621 (3)0.1412 (4)0.0640 (11)
C20.4386 (4)0.4665 (3)0.1935 (4)0.0492 (10)
N30.1246 (5)0.0994 (3)0.1516 (4)0.0687 (12)
C30.3944 (4)0.3437 (3)0.0250 (4)0.0506 (11)
N40.2023 (3)0.0434 (3)0.0210 (3)0.0462 (8)
C40.2240 (4)0.2126 (4)0.1264 (4)0.0526 (11)
H4B0.17060.27430.12940.063*
H4C0.20410.18010.21010.063*
C50.1892 (4)0.1415 (3)0.0289 (4)0.0436 (9)
C60.1615 (4)0.0195 (3)0.0926 (4)0.0423 (9)
C70.1625 (4)0.0868 (3)0.1392 (4)0.0421 (9)
C80.2228 (5)0.1601 (3)0.0731 (4)0.0520 (11)
H8A0.26070.13970.00410.062*
C90.2273 (5)0.2620 (4)0.1082 (5)0.0612 (13)
H9A0.26720.31020.06280.073*
C100.1719 (5)0.2925 (4)0.2116 (5)0.0622 (13)
H10A0.17570.36110.23670.075*
C110.1115 (5)0.2215 (4)0.2769 (5)0.0592 (12)
H11A0.07270.24380.34460.071*
C120.1061 (4)0.1176 (3)0.2458 (4)0.0447 (10)
C130.0405 (5)0.0452 (4)0.3241 (5)0.0636 (13)
H13A0.01050.08270.39130.095*
H13B0.03350.01310.27010.095*
H13C0.10230.00670.36100.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.110 (3)0.0366 (16)0.074 (2)0.0038 (17)0.058 (2)0.0004 (15)
S10.0509 (7)0.0809 (10)0.0723 (8)0.0051 (6)0.0203 (6)0.0044 (7)
N10.062 (3)0.055 (3)0.097 (3)0.003 (2)0.028 (2)0.012 (2)
C10.086 (4)0.072 (4)0.071 (3)0.008 (3)0.021 (3)0.014 (3)
S20.0675 (8)0.0563 (7)0.0718 (8)0.0028 (6)0.0393 (6)0.0030 (6)
N20.062 (3)0.054 (2)0.079 (3)0.006 (2)0.021 (2)0.010 (2)
C20.046 (2)0.055 (3)0.048 (2)0.000 (2)0.0133 (19)0.008 (2)
N30.110 (3)0.040 (2)0.072 (3)0.001 (2)0.059 (3)0.000 (2)
C30.049 (2)0.049 (3)0.060 (3)0.003 (2)0.025 (2)0.014 (2)
N40.064 (2)0.0383 (19)0.0408 (19)0.0034 (17)0.0222 (16)0.0005 (15)
C40.067 (3)0.049 (3)0.044 (2)0.002 (2)0.018 (2)0.003 (2)
C50.046 (2)0.048 (2)0.040 (2)0.0010 (19)0.0138 (17)0.0027 (19)
C60.049 (2)0.039 (2)0.043 (2)0.0028 (18)0.0196 (18)0.0031 (18)
C70.047 (2)0.039 (2)0.043 (2)0.0015 (18)0.0151 (18)0.0009 (18)
C80.068 (3)0.042 (2)0.054 (3)0.003 (2)0.031 (2)0.003 (2)
C90.077 (3)0.042 (3)0.070 (3)0.008 (2)0.029 (3)0.002 (2)
C100.070 (3)0.037 (2)0.083 (4)0.001 (2)0.021 (3)0.011 (2)
C110.056 (3)0.061 (3)0.066 (3)0.005 (2)0.024 (2)0.017 (2)
C120.041 (2)0.050 (2)0.045 (2)0.0001 (19)0.0127 (17)0.0076 (19)
C130.073 (3)0.064 (3)0.064 (3)0.003 (3)0.039 (3)0.003 (2)
Geometric parameters (Å, º) top
O—C51.343 (5)C4—H4B0.9700
O—N31.418 (5)C4—H4C0.9700
S1—C31.706 (5)C6—C71.467 (5)
S1—C21.727 (5)C7—C81.394 (6)
N1—C31.293 (5)C7—C121.420 (5)
N1—N21.381 (6)C8—C91.373 (6)
C1—C21.491 (6)C8—H8A0.9300
C1—H1B0.9600C9—C101.383 (6)
C1—H1C0.9600C9—H9A0.9300
C1—H1D0.9600C10—C111.370 (7)
S2—C31.759 (5)C10—H10A0.9300
S2—C41.809 (5)C11—C121.389 (6)
N2—C21.287 (6)C11—H11A0.9300
N3—C61.304 (5)C12—C131.496 (6)
N4—C51.283 (5)C13—H13A0.9600
N4—C61.382 (5)C13—H13B0.9600
C4—C51.479 (6)C13—H13C0.9600
C5—O—N3106.1 (3)N3—C6—N4113.6 (4)
C3—S1—C287.5 (2)N3—C6—C7125.0 (4)
C3—N1—N2111.8 (4)N4—C6—C7121.4 (3)
C2—C1—H1B109.5C8—C7—C12119.6 (4)
C2—C1—H1C109.5C8—C7—C6116.8 (4)
H1B—C1—H1C109.5C12—C7—C6123.7 (4)
C2—C1—H1D109.5C9—C8—C7121.2 (4)
H1B—C1—H1D109.5C9—C8—H8A119.4
H1C—C1—H1D109.5C7—C8—H8A119.4
C3—S2—C4100.5 (2)C8—C9—C10119.5 (4)
C2—N2—N1113.5 (4)C8—C9—H9A120.3
N2—C2—C1123.4 (4)C10—C9—H9A120.3
N2—C2—S1112.8 (3)C11—C10—C9120.0 (4)
C1—C2—S1123.7 (4)C11—C10—H10A120.0
C6—N3—O103.5 (3)C9—C10—H10A120.0
N1—C3—S1114.3 (4)C10—C11—C12122.5 (4)
N1—C3—S2124.1 (4)C10—C11—H11A118.8
S1—C3—S2121.6 (3)C12—C11—H11A118.8
C5—N4—C6103.6 (3)C11—C12—C7117.2 (4)
C5—C4—S2111.8 (3)C11—C12—C13118.8 (4)
C5—C4—H4B109.3C7—C12—C13123.9 (4)
S2—C4—H4B109.3C12—C13—H13A109.5
C5—C4—H4C109.3C12—C13—H13B109.5
S2—C4—H4C109.3H13A—C13—H13B109.5
H4B—C4—H4C107.9C12—C13—H13C109.5
N4—C5—O113.2 (4)H13A—C13—H13C109.5
N4—C5—C4129.0 (4)H13B—C13—H13C109.5
O—C5—C4117.6 (4)
C3—N1—N2—C20.1 (6)O—N3—C6—N40.4 (5)
N1—N2—C2—C1178.5 (4)O—N3—C6—C7179.1 (4)
N1—N2—C2—S10.8 (5)C5—N4—C6—N30.2 (5)
C3—S1—C2—N21.0 (4)C5—N4—C6—C7179.3 (4)
C3—S1—C2—C1178.6 (4)N3—C6—C7—C8171.0 (5)
C5—O—N3—C60.4 (5)N4—C6—C7—C88.4 (6)
N2—N1—C3—S10.6 (5)N3—C6—C7—C129.0 (7)
N2—N1—C3—S2179.6 (3)N4—C6—C7—C12171.6 (4)
C2—S1—C3—N10.9 (4)C12—C7—C8—C90.9 (7)
C2—S1—C3—S2179.9 (3)C6—C7—C8—C9179.1 (4)
C4—S2—C3—N117.8 (4)C7—C8—C9—C100.5 (8)
C4—S2—C3—S1161.1 (3)C8—C9—C10—C111.0 (8)
C3—S2—C4—C580.5 (3)C9—C10—C11—C121.8 (8)
C6—N4—C5—O0.1 (5)C10—C11—C12—C72.1 (7)
C6—N4—C5—C4176.4 (4)C10—C11—C12—C13178.8 (5)
N3—O—C5—N40.4 (5)C8—C7—C12—C111.6 (6)
N3—O—C5—C4177.1 (4)C6—C7—C12—C11178.4 (4)
S2—C4—C5—N483.2 (5)C8—C7—C12—C13179.3 (4)
S2—C4—C5—O92.9 (4)C6—C7—C12—C130.7 (7)

Experimental details

Crystal data
Chemical formulaC13H12N4OS2
Mr304.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.309 (2), 12.992 (3), 10.600 (2)
β (°) 100.63 (3)
V3)1395.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.30 × 0.10 × 0.10
Data collection
DiffractometerNonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.894, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
2890, 2737, 1694
Rint0.032
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.178, 1.03
No. of reflections2737
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.35

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

 

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