Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046910/dn2233sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046910/dn2233Isup2.hkl |
CCDC reference: 663849
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.076
- wR factor = 0.204
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S2 - C10 .. 6.61 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
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 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Nicolaides et al. (1998); Romero (2001); Talar & Dejai (1996).
5-Mercapto-2-methyl-1,3,4-thiadiazole (30 mmol) was dissolve in ethanol (70 ml) and water (70 mmol). Sodium acetate (30 mmol) was added to this mixture·Then 3-phenyl-5-chloromethyl-1,2,4-oxadiazol (50 mmol) was added. The resulting mixture was refluxed for 8 h. After cooling and filtrating, crude compound (I) was gained. Pure compound (I) was obstained by crystallizing from a mixture of ethyl acetate (6 ml) and petrolum ether (6 ml). Crystals of (I) suitable for X-ray diffraction were obstained by slow evaporation of an ethanol solution. 1H NMR (CDCl3, δ, p.p.m.): 8.05–8.09(m, 2H), 7.48–7.51 (m, 3H), 4.81–4.82 (s, 2H), 2.76–2.77 (s,2H).
All H atoms were placed geometrically and treated as riding on their parent atoms with C—H= 0.93 Å(aromatic), 0.97 Å (methylene) and 0.96 Å (methyl) with Uiso(H) = 1.2 or 1.5(methyl)Ueq(C).
1,2,4-Oxadiazoles represent an important class of five-membered heterocycles. Some derivatives of 1,2,4-oxadiazoles have anti-inflammatory (Nicolaides et al., 1998) and antipicornaviral (Romero, 2001) properties. We are focusing our synthetic and structural studies on new oxindole derivatives. The sulfurether compounds exhibited considerably strong inhibiting activity to Staphylococcus aureus (Talar & Dejai, 1996). We report here the structure of its close analogue with thiadiazole sulfanylether group, (I).
The molecule is built up from a phenyl substituted oxadiazole linked to a methyl-thiadiazole through a methylenethio linker. The benzene and oxadiazole ring are roughly coplanar making a twist angle of only 4.6 (3)° whereas the thiadiazole ring make a dihedral angle of 87.9 (3)° with the oxadiazole ring (Fig. 1).
For related literature, see: Nicolaides et al. (1998); Romero (2001); Talar & Dejai (1996).
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: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. A view of the molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C12H10N4OS2 | F(000) = 600 |
Mr = 290.36 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 25 reflections |
a = 9.926 (2) Å | θ = 9–12° |
b = 5.9340 (12) Å | µ = 0.40 mm−1 |
c = 23.049 (5) Å | T = 293 K |
β = 100.39 (3)° | Block, colourless |
V = 1335.3 (5) Å3 | 0.40 × 0.10 × 0.10 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1492 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.065 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
ω/2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→7 |
Tmin = 0.858, Tmax = 0.962 | l = 0→28 |
2764 measured reflections | 3 standard reflections every 200 reflections |
2608 independent reflections | intensity decay: none |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.204 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.04P)2 + 7P] where P = (Fo2 + 2Fc2)/3 |
2608 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
C12H10N4OS2 | V = 1335.3 (5) Å3 |
Mr = 290.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.926 (2) Å | µ = 0.40 mm−1 |
b = 5.9340 (12) Å | T = 293 K |
c = 23.049 (5) Å | 0.40 × 0.10 × 0.10 mm |
β = 100.39 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1492 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.065 |
Tmin = 0.858, Tmax = 0.962 | 3 standard reflections every 200 reflections |
2764 measured reflections | intensity decay: none |
2608 independent reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.204 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.47 e Å−3 |
2608 reflections | Δρmin = −0.50 e Å−3 |
172 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 | 0.29941 (17) | 0.5721 (2) | 0.27537 (7) | 0.0558 (5) | |
S2 | 0.05050 (19) | 0.4212 (3) | 0.18937 (8) | 0.0710 (6) | |
O1 | 0.4942 (5) | 0.0277 (7) | 0.33950 (18) | 0.0609 (12) | |
N1 | 0.3586 (5) | 0.2231 (8) | 0.3857 (2) | 0.0477 (11) | |
N2 | 0.4626 (5) | −0.1135 (8) | 0.3843 (2) | 0.0562 (13) | |
N3 | 0.2582 (5) | 0.1682 (9) | 0.2216 (2) | 0.0681 (16) | |
N4 | 0.1670 (5) | 0.0436 (10) | 0.1801 (3) | 0.0761 (18) | |
C1 | 0.2304 (8) | −0.1991 (13) | 0.5618 (3) | 0.077 (2) | |
H1A | 0.1983 | −0.2411 | 0.5957 | 0.093* | |
C2 | 0.1964 (7) | 0.0078 (15) | 0.5358 (3) | 0.079 (2) | |
H2B | 0.1396 | 0.1044 | 0.5522 | 0.095* | |
C3 | 0.2448 (7) | 0.0740 (11) | 0.4862 (3) | 0.0658 (18) | |
H3B | 0.2206 | 0.2138 | 0.4693 | 0.079* | |
C4 | 0.3295 (6) | −0.0677 (10) | 0.4615 (2) | 0.0469 (13) | |
C5 | 0.3619 (6) | −0.2772 (10) | 0.4860 (3) | 0.0538 (15) | |
H5A | 0.4164 | −0.3752 | 0.4688 | 0.065* | |
C6 | 0.3123 (7) | −0.3418 (12) | 0.5367 (3) | 0.0649 (18) | |
H6A | 0.3350 | −0.4825 | 0.5534 | 0.078* | |
C7 | 0.3822 (5) | 0.0092 (9) | 0.4097 (2) | 0.0388 (12) | |
C8 | 0.4290 (6) | 0.2220 (10) | 0.3438 (3) | 0.0502 (14) | |
C9 | 0.4496 (6) | 0.4124 (10) | 0.3049 (2) | 0.0510 (14) | |
H9A | 0.4884 | 0.3538 | 0.2722 | 0.061* | |
H9B | 0.5165 | 0.5140 | 0.3269 | 0.061* | |
C10 | 0.2114 (6) | 0.3699 (9) | 0.2295 (3) | 0.0484 (14) | |
C11 | 0.0558 (6) | 0.1539 (11) | 0.1618 (3) | 0.0591 (16) | |
C12 | −0.0546 (7) | 0.0550 (13) | 0.1150 (3) | 0.081 (2) | |
H12A | −0.0309 | −0.0971 | 0.1069 | 0.122* | |
H12B | −0.0628 | 0.1433 | 0.0797 | 0.122* | |
H12C | −0.1402 | 0.0561 | 0.1288 | 0.122* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0789 (11) | 0.0321 (8) | 0.0584 (9) | −0.0002 (8) | 0.0180 (8) | −0.0005 (7) |
S2 | 0.0760 (12) | 0.0531 (11) | 0.0816 (12) | 0.0154 (9) | 0.0081 (9) | −0.0025 (9) |
O1 | 0.094 (3) | 0.038 (2) | 0.056 (2) | 0.008 (2) | 0.028 (2) | 0.001 (2) |
N1 | 0.058 (3) | 0.034 (3) | 0.054 (3) | 0.002 (2) | 0.018 (2) | 0.001 (2) |
N2 | 0.079 (4) | 0.036 (3) | 0.055 (3) | 0.011 (3) | 0.016 (3) | −0.001 (2) |
N3 | 0.070 (4) | 0.049 (3) | 0.078 (4) | 0.013 (3) | −0.006 (3) | −0.017 (3) |
N4 | 0.067 (4) | 0.057 (4) | 0.096 (4) | 0.006 (3) | −0.009 (3) | −0.031 (3) |
C1 | 0.102 (6) | 0.073 (5) | 0.064 (4) | −0.005 (5) | 0.034 (4) | 0.019 (4) |
C2 | 0.078 (5) | 0.095 (6) | 0.075 (5) | 0.010 (4) | 0.042 (4) | 0.012 (4) |
C3 | 0.088 (5) | 0.042 (4) | 0.074 (4) | 0.013 (3) | 0.033 (4) | 0.012 (3) |
C4 | 0.056 (3) | 0.035 (3) | 0.049 (3) | −0.006 (3) | 0.009 (3) | −0.006 (3) |
C5 | 0.067 (4) | 0.033 (3) | 0.058 (4) | 0.003 (3) | 0.003 (3) | 0.000 (3) |
C6 | 0.084 (5) | 0.052 (4) | 0.059 (4) | −0.015 (4) | 0.012 (3) | 0.010 (3) |
C7 | 0.039 (3) | 0.034 (3) | 0.040 (3) | 0.002 (2) | −0.001 (2) | −0.005 (2) |
C8 | 0.069 (4) | 0.034 (3) | 0.049 (3) | −0.002 (3) | 0.015 (3) | −0.005 (3) |
C9 | 0.057 (3) | 0.050 (4) | 0.046 (3) | 0.000 (3) | 0.007 (3) | −0.008 (3) |
C10 | 0.048 (3) | 0.037 (3) | 0.060 (3) | 0.003 (3) | 0.008 (3) | 0.007 (3) |
C11 | 0.064 (4) | 0.047 (4) | 0.064 (4) | 0.007 (3) | 0.007 (3) | 0.005 (3) |
C12 | 0.080 (5) | 0.074 (5) | 0.084 (5) | −0.005 (4) | −0.001 (4) | −0.012 (4) |
S1—C10 | 1.729 (6) | C2—H2B | 0.9300 |
S1—C9 | 1.794 (6) | C3—C4 | 1.382 (8) |
S2—C11 | 1.714 (7) | C3—H3B | 0.9300 |
S2—C10 | 1.722 (6) | C4—C5 | 1.378 (8) |
O1—C8 | 1.335 (7) | C4—C7 | 1.461 (7) |
O1—N2 | 1.408 (6) | C5—C6 | 1.401 (8) |
N1—C8 | 1.291 (7) | C5—H5A | 0.9300 |
N1—C7 | 1.388 (7) | C6—H6A | 0.9300 |
N2—C7 | 1.296 (7) | C8—C9 | 1.480 (8) |
N3—C10 | 1.308 (7) | C9—H9A | 0.9700 |
N3—N4 | 1.403 (6) | C9—H9B | 0.9700 |
N4—C11 | 1.287 (7) | C11—C12 | 1.510 (8) |
C1—C6 | 1.372 (10) | C12—H12A | 0.9600 |
C1—C2 | 1.381 (10) | C12—H12B | 0.9600 |
C1—H1A | 0.9300 | C12—H12C | 0.9600 |
C2—C3 | 1.375 (9) | ||
C10—S1—C9 | 99.1 (3) | N2—C7—N1 | 114.0 (5) |
C11—S2—C10 | 87.0 (3) | N2—C7—C4 | 122.4 (5) |
C8—O1—N2 | 106.5 (4) | N1—C7—C4 | 123.5 (5) |
C8—N1—C7 | 102.6 (5) | N1—C8—O1 | 113.3 (5) |
C7—N2—O1 | 103.6 (4) | N1—C8—C9 | 127.1 (5) |
C10—N3—N4 | 112.1 (5) | O1—C8—C9 | 119.5 (5) |
C11—N4—N3 | 111.4 (5) | C8—C9—S1 | 115.9 (4) |
C6—C1—C2 | 118.9 (6) | C8—C9—H9A | 108.3 |
C6—C1—H1A | 120.6 | S1—C9—H9A | 108.3 |
C2—C1—H1A | 120.6 | C8—C9—H9B | 108.3 |
C3—C2—C1 | 121.3 (7) | S1—C9—H9B | 108.3 |
C3—C2—H2B | 119.4 | H9A—C9—H9B | 107.4 |
C1—C2—H2B | 119.4 | N3—C10—S2 | 113.9 (4) |
C2—C3—C4 | 119.9 (6) | N3—C10—S1 | 124.6 (4) |
C2—C3—H3B | 120.1 | S2—C10—S1 | 121.5 (3) |
C4—C3—H3B | 120.1 | N4—C11—C12 | 120.4 (6) |
C5—C4—C3 | 119.7 (6) | N4—C11—S2 | 115.5 (5) |
C5—C4—C7 | 121.6 (5) | C12—C11—S2 | 123.9 (5) |
C3—C4—C7 | 118.7 (5) | C11—C12—H12A | 109.5 |
C4—C5—C6 | 119.8 (6) | C11—C12—H12B | 109.5 |
C4—C5—H5A | 120.1 | H12A—C12—H12B | 109.5 |
C6—C5—H5A | 120.1 | C11—C12—H12C | 109.5 |
C1—C6—C5 | 120.5 (6) | H12A—C12—H12C | 109.5 |
C1—C6—H6A | 119.8 | H12B—C12—H12C | 109.5 |
C5—C6—H6A | 119.8 | ||
C8—O1—N2—C7 | 0.5 (6) | C7—N1—C8—O1 | −0.1 (6) |
C10—N3—N4—C11 | −3.0 (8) | C7—N1—C8—C9 | −175.9 (6) |
C6—C1—C2—C3 | −1.1 (12) | N2—O1—C8—N1 | −0.2 (7) |
C1—C2—C3—C4 | −0.2 (12) | N2—O1—C8—C9 | 175.9 (5) |
C2—C3—C4—C5 | 1.8 (10) | N1—C8—C9—S1 | −45.1 (8) |
C2—C3—C4—C7 | −178.5 (6) | O1—C8—C9—S1 | 139.4 (5) |
C3—C4—C5—C6 | −2.1 (9) | C10—S1—C9—C8 | −67.6 (5) |
C7—C4—C5—C6 | 178.2 (5) | N4—N3—C10—S2 | 2.2 (7) |
C2—C1—C6—C5 | 0.8 (11) | N4—N3—C10—S1 | −177.6 (5) |
C4—C5—C6—C1 | 0.8 (10) | C11—S2—C10—N3 | −0.7 (5) |
O1—N2—C7—N1 | −0.6 (6) | C11—S2—C10—S1 | 179.1 (4) |
O1—N2—C7—C4 | −176.7 (5) | C9—S1—C10—N3 | −2.5 (6) |
C8—N1—C7—N2 | 0.4 (6) | C9—S1—C10—S2 | 177.7 (4) |
C8—N1—C7—C4 | 176.5 (5) | N3—N4—C11—C12 | 177.5 (6) |
C5—C4—C7—N2 | −0.5 (8) | N3—N4—C11—S2 | 2.5 (8) |
C3—C4—C7—N2 | 179.7 (6) | C10—S2—C11—N4 | −1.1 (6) |
C5—C4—C7—N1 | −176.2 (5) | C10—S2—C11—C12 | −175.9 (6) |
C3—C4—C7—N1 | 4.0 (8) |
Experimental details
Crystal data | |
Chemical formula | C12H10N4OS2 |
Mr | 290.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.926 (2), 5.9340 (12), 23.049 (5) |
β (°) | 100.39 (3) |
V (Å3) | 1335.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.40 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.858, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2764, 2608, 1492 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.204, 1.00 |
No. of reflections | 2608 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.50 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).
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1,2,4-Oxadiazoles represent an important class of five-membered heterocycles. Some derivatives of 1,2,4-oxadiazoles have anti-inflammatory (Nicolaides et al., 1998) and antipicornaviral (Romero, 2001) properties. We are focusing our synthetic and structural studies on new oxindole derivatives. The sulfurether compounds exhibited considerably strong inhibiting activity to Staphylococcus aureus (Talar & Dejai, 1996). We report here the structure of its close analogue with thiadiazole sulfanylether group, (I).
The molecule is built up from a phenyl substituted oxadiazole linked to a methyl-thiadiazole through a methylenethio linker. The benzene and oxadiazole ring are roughly coplanar making a twist angle of only 4.6 (3)° whereas the thiadiazole ring make a dihedral angle of 87.9 (3)° with the oxadiazole ring (Fig. 1).