Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054682/hb2618sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054682/hb2618Isup2.hkl |
CCDC reference: 674079
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
For related literature, see: Nicolaides et al. (1998); Romero (2001); Talar & Dejai (1996).
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).
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).
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).
Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level (H atoms represented by arbitrary spheres). |
C13H12N4OS2 | F(000) = 632 |
Mr = 304.39 | Dx = 1.449 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 10.309 (2) Å | θ = 9–13° |
b = 12.992 (3) Å | µ = 0.38 mm−1 |
c = 10.600 (2) Å | T = 293 K |
β = 100.63 (3)° | Block, colourless |
V = 1395.3 (5) Å3 | 0.30 × 0.10 × 0.10 mm |
Z = 4 |
Nonius CAD-4 diffractometer | 1694 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 26.0°, θmin = 2.0° |
ω/2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→16 |
Tmin = 0.894, Tmax = 0.963 | l = 0→13 |
2890 measured reflections | 3 standard reflections every 200 reflections |
2737 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C13H12N4OS2 | V = 1395.3 (5) Å3 |
Mr = 304.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.309 (2) Å | µ = 0.38 mm−1 |
b = 12.992 (3) Å | T = 293 K |
c = 10.600 (2) Å | 0.30 × 0.10 × 0.10 mm |
β = 100.63 (3)° |
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 = 0.963 | 3 standard reflections every 200 reflections |
2890 measured reflections | intensity decay: none |
2737 independent reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
2737 reflections | Δρmin = −0.35 e Å−3 |
181 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 | ||
O | 0.1434 (4) | 0.1828 (2) | 0.0705 (3) | 0.0684 (10) | |
S1 | 0.53469 (12) | 0.38060 (11) | 0.12681 (13) | 0.0669 (4) | |
N1 | 0.2889 (4) | 0.3910 (3) | 0.0430 (4) | 0.0695 (12) | |
C1 | 0.4913 (6) | 0.5355 (4) | 0.3034 (5) | 0.0754 (15) | |
H1B | 0.4209 | 0.5770 | 0.3239 | 0.113* | |
H1C | 0.5582 | 0.5793 | 0.2804 | 0.113* | |
H1D | 0.5286 | 0.4947 | 0.3766 | 0.113* | |
S2 | 0.39670 (13) | 0.24762 (10) | −0.09151 (13) | 0.0618 (4) | |
N2 | 0.3157 (4) | 0.4621 (3) | 0.1412 (4) | 0.0640 (11) | |
C2 | 0.4386 (4) | 0.4665 (3) | 0.1935 (4) | 0.0492 (10) | |
N3 | 0.1246 (5) | 0.0994 (3) | 0.1516 (4) | 0.0687 (12) | |
C3 | 0.3944 (4) | 0.3437 (3) | 0.0250 (4) | 0.0506 (11) | |
N4 | 0.2023 (3) | 0.0434 (3) | −0.0210 (3) | 0.0462 (8) | |
C4 | 0.2240 (4) | 0.2126 (4) | −0.1264 (4) | 0.0526 (11) | |
H4B | 0.1706 | 0.2743 | −0.1294 | 0.063* | |
H4C | 0.2041 | 0.1801 | −0.2101 | 0.063* | |
C5 | 0.1892 (4) | 0.1415 (3) | −0.0289 (4) | 0.0436 (9) | |
C6 | 0.1615 (4) | 0.0195 (3) | 0.0926 (4) | 0.0423 (9) | |
C7 | 0.1625 (4) | −0.0868 (3) | 0.1392 (4) | 0.0421 (9) | |
C8 | 0.2228 (5) | −0.1601 (3) | 0.0731 (4) | 0.0520 (11) | |
H8A | 0.2607 | −0.1397 | 0.0041 | 0.062* | |
C9 | 0.2273 (5) | −0.2620 (4) | 0.1082 (5) | 0.0612 (13) | |
H9A | 0.2672 | −0.3102 | 0.0628 | 0.073* | |
C10 | 0.1719 (5) | −0.2925 (4) | 0.2116 (5) | 0.0622 (13) | |
H10A | 0.1757 | −0.3611 | 0.2367 | 0.075* | |
C11 | 0.1115 (5) | −0.2215 (4) | 0.2769 (5) | 0.0592 (12) | |
H11A | 0.0727 | −0.2438 | 0.3446 | 0.071* | |
C12 | 0.1061 (4) | −0.1176 (3) | 0.2458 (4) | 0.0447 (10) | |
C13 | 0.0405 (5) | −0.0452 (4) | 0.3241 (5) | 0.0636 (13) | |
H13A | 0.0105 | −0.0827 | 0.3913 | 0.095* | |
H13B | −0.0335 | −0.0131 | 0.2701 | 0.095* | |
H13C | 0.1023 | 0.0067 | 0.3610 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O | 0.110 (3) | 0.0366 (16) | 0.074 (2) | 0.0038 (17) | 0.058 (2) | −0.0004 (15) |
S1 | 0.0509 (7) | 0.0809 (10) | 0.0723 (8) | 0.0051 (6) | 0.0203 (6) | −0.0044 (7) |
N1 | 0.062 (3) | 0.055 (3) | 0.097 (3) | 0.003 (2) | 0.028 (2) | −0.012 (2) |
C1 | 0.086 (4) | 0.072 (4) | 0.071 (3) | −0.008 (3) | 0.021 (3) | −0.014 (3) |
S2 | 0.0675 (8) | 0.0563 (7) | 0.0718 (8) | −0.0028 (6) | 0.0393 (6) | −0.0030 (6) |
N2 | 0.062 (3) | 0.054 (2) | 0.079 (3) | 0.006 (2) | 0.021 (2) | −0.010 (2) |
C2 | 0.046 (2) | 0.055 (3) | 0.048 (2) | 0.000 (2) | 0.0133 (19) | 0.008 (2) |
N3 | 0.110 (3) | 0.040 (2) | 0.072 (3) | −0.001 (2) | 0.059 (3) | 0.000 (2) |
C3 | 0.049 (2) | 0.049 (3) | 0.060 (3) | 0.003 (2) | 0.025 (2) | 0.014 (2) |
N4 | 0.064 (2) | 0.0383 (19) | 0.0408 (19) | 0.0034 (17) | 0.0222 (16) | −0.0005 (15) |
C4 | 0.067 (3) | 0.049 (3) | 0.044 (2) | 0.002 (2) | 0.018 (2) | 0.003 (2) |
C5 | 0.046 (2) | 0.048 (2) | 0.040 (2) | 0.0010 (19) | 0.0138 (17) | −0.0027 (19) |
C6 | 0.049 (2) | 0.039 (2) | 0.043 (2) | 0.0028 (18) | 0.0196 (18) | 0.0031 (18) |
C7 | 0.047 (2) | 0.039 (2) | 0.043 (2) | −0.0015 (18) | 0.0151 (18) | 0.0009 (18) |
C8 | 0.068 (3) | 0.042 (2) | 0.054 (3) | −0.003 (2) | 0.031 (2) | −0.003 (2) |
C9 | 0.077 (3) | 0.042 (3) | 0.070 (3) | 0.008 (2) | 0.029 (3) | 0.002 (2) |
C10 | 0.070 (3) | 0.037 (2) | 0.083 (4) | −0.001 (2) | 0.021 (3) | 0.011 (2) |
C11 | 0.056 (3) | 0.061 (3) | 0.066 (3) | −0.005 (2) | 0.024 (2) | 0.017 (2) |
C12 | 0.041 (2) | 0.050 (2) | 0.045 (2) | 0.0001 (19) | 0.0127 (17) | 0.0076 (19) |
C13 | 0.073 (3) | 0.064 (3) | 0.064 (3) | −0.003 (3) | 0.039 (3) | 0.003 (2) |
O—C5 | 1.343 (5) | C4—H4B | 0.9700 |
O—N3 | 1.418 (5) | C4—H4C | 0.9700 |
S1—C3 | 1.706 (5) | C6—C7 | 1.467 (5) |
S1—C2 | 1.727 (5) | C7—C8 | 1.394 (6) |
N1—C3 | 1.293 (5) | C7—C12 | 1.420 (5) |
N1—N2 | 1.381 (6) | C8—C9 | 1.373 (6) |
C1—C2 | 1.491 (6) | C8—H8A | 0.9300 |
C1—H1B | 0.9600 | C9—C10 | 1.383 (6) |
C1—H1C | 0.9600 | C9—H9A | 0.9300 |
C1—H1D | 0.9600 | C10—C11 | 1.370 (7) |
S2—C3 | 1.759 (5) | C10—H10A | 0.9300 |
S2—C4 | 1.809 (5) | C11—C12 | 1.389 (6) |
N2—C2 | 1.287 (6) | C11—H11A | 0.9300 |
N3—C6 | 1.304 (5) | C12—C13 | 1.496 (6) |
N4—C5 | 1.283 (5) | C13—H13A | 0.9600 |
N4—C6 | 1.382 (5) | C13—H13B | 0.9600 |
C4—C5 | 1.479 (6) | C13—H13C | 0.9600 |
C5—O—N3 | 106.1 (3) | N3—C6—N4 | 113.6 (4) |
C3—S1—C2 | 87.5 (2) | N3—C6—C7 | 125.0 (4) |
C3—N1—N2 | 111.8 (4) | N4—C6—C7 | 121.4 (3) |
C2—C1—H1B | 109.5 | C8—C7—C12 | 119.6 (4) |
C2—C1—H1C | 109.5 | C8—C7—C6 | 116.8 (4) |
H1B—C1—H1C | 109.5 | C12—C7—C6 | 123.7 (4) |
C2—C1—H1D | 109.5 | C9—C8—C7 | 121.2 (4) |
H1B—C1—H1D | 109.5 | C9—C8—H8A | 119.4 |
H1C—C1—H1D | 109.5 | C7—C8—H8A | 119.4 |
C3—S2—C4 | 100.5 (2) | C8—C9—C10 | 119.5 (4) |
C2—N2—N1 | 113.5 (4) | C8—C9—H9A | 120.3 |
N2—C2—C1 | 123.4 (4) | C10—C9—H9A | 120.3 |
N2—C2—S1 | 112.8 (3) | C11—C10—C9 | 120.0 (4) |
C1—C2—S1 | 123.7 (4) | C11—C10—H10A | 120.0 |
C6—N3—O | 103.5 (3) | C9—C10—H10A | 120.0 |
N1—C3—S1 | 114.3 (4) | C10—C11—C12 | 122.5 (4) |
N1—C3—S2 | 124.1 (4) | C10—C11—H11A | 118.8 |
S1—C3—S2 | 121.6 (3) | C12—C11—H11A | 118.8 |
C5—N4—C6 | 103.6 (3) | C11—C12—C7 | 117.2 (4) |
C5—C4—S2 | 111.8 (3) | C11—C12—C13 | 118.8 (4) |
C5—C4—H4B | 109.3 | C7—C12—C13 | 123.9 (4) |
S2—C4—H4B | 109.3 | C12—C13—H13A | 109.5 |
C5—C4—H4C | 109.3 | C12—C13—H13B | 109.5 |
S2—C4—H4C | 109.3 | H13A—C13—H13B | 109.5 |
H4B—C4—H4C | 107.9 | C12—C13—H13C | 109.5 |
N4—C5—O | 113.2 (4) | H13A—C13—H13C | 109.5 |
N4—C5—C4 | 129.0 (4) | H13B—C13—H13C | 109.5 |
O—C5—C4 | 117.6 (4) | ||
C3—N1—N2—C2 | 0.1 (6) | O—N3—C6—N4 | −0.4 (5) |
N1—N2—C2—C1 | −178.5 (4) | O—N3—C6—C7 | 179.1 (4) |
N1—N2—C2—S1 | −0.8 (5) | C5—N4—C6—N3 | 0.2 (5) |
C3—S1—C2—N2 | 1.0 (4) | C5—N4—C6—C7 | −179.3 (4) |
C3—S1—C2—C1 | 178.6 (4) | N3—C6—C7—C8 | −171.0 (5) |
C5—O—N3—C6 | 0.4 (5) | N4—C6—C7—C8 | 8.4 (6) |
N2—N1—C3—S1 | 0.6 (5) | N3—C6—C7—C12 | 9.0 (7) |
N2—N1—C3—S2 | 179.6 (3) | N4—C6—C7—C12 | −171.6 (4) |
C2—S1—C3—N1 | −0.9 (4) | C12—C7—C8—C9 | 0.9 (7) |
C2—S1—C3—S2 | −179.9 (3) | C6—C7—C8—C9 | −179.1 (4) |
C4—S2—C3—N1 | −17.8 (4) | C7—C8—C9—C10 | −0.5 (8) |
C4—S2—C3—S1 | 161.1 (3) | C8—C9—C10—C11 | 1.0 (8) |
C3—S2—C4—C5 | −80.5 (3) | C9—C10—C11—C12 | −1.8 (8) |
C6—N4—C5—O | 0.1 (5) | C10—C11—C12—C7 | 2.1 (7) |
C6—N4—C5—C4 | 176.4 (4) | C10—C11—C12—C13 | −178.8 (5) |
N3—O—C5—N4 | −0.4 (5) | C8—C7—C12—C11 | −1.6 (6) |
N3—O—C5—C4 | −177.1 (4) | C6—C7—C12—C11 | 178.4 (4) |
S2—C4—C5—N4 | −83.2 (5) | C8—C7—C12—C13 | 179.3 (4) |
S2—C4—C5—O | 92.9 (4) | C6—C7—C12—C13 | −0.7 (7) |
Experimental details
Crystal data | |
Chemical formula | C13H12N4OS2 |
Mr | 304.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.309 (2), 12.992 (3), 10.600 (2) |
β (°) | 100.63 (3) |
V (Å3) | 1395.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.30 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.894, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2890, 2737, 1694 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.178, 1.03 |
No. of reflections | 2737 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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.