Acta Cryst. (2008). E64, o412 [ doi:10.1107/S1600536807068286 ]
In the molecule of the title compound, C11H15N5OS2, the thiadiazole and triazole rings are not coplanar, the dihedral angle formed by their mean planes being 59.9 (2)°. The exocyclic S atom, and the methylene, carbonyl, tert-butyl and one methyl carbon form an approximately planar zigzag chain, which makes a dihedral angle of 74.6 (1)° with the thiadiazole ring.
8 mmol of 5-((1H-1,2,4-triazol-1-yl)methyl)-1,3,4-thiadiazole-2(3H)-thione (Hu et al., 2006; Xu et al., 2005; Xu et al., 2006) was refluxed for 4 h with 8 mmol of 1-bromo-3,3-dimethylbutan-2-one in 50 ml of acetone in the presence of 8 mmol of triethylamine. The solid that precipitated was recrystallized from ethanol (1.21 g, yield 50.86%). Single crystals suitable for X-ray measurements were obtained by slow evaporation of ethylacetate solution at room temperature.
After the H atoms were located in the difference map, they were fixed geometrically in the idealized positions and allowed to ride on the parent C atoms, with C—H distances of 0.96 Å (methyl), 0.97 Å (CH2) or 0.93 Å (CH), and with Uiso(H) values of 1.2Ueq(C) and 1.5 Ueq(C) (for methyl H atoms).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
![[Figure 1]](./ya2060fig1thm.gif)
| Fig. 1. The structure of the title compound (I), showing 50% probability displacement ellipsoids and the atom numbering scheme. |
| C11H15N5OS2 | Z = 2 |
| Mr = 297.40 | F(000) = 312 |
| Triclinic, P1 | Dx = 1.351 Mg m−3 |
| a = 8.9723 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 10.1103 (8) Å | Cell parameters from 2210 reflections |
| c = 10.1734 (8) Å | θ = 2.5–25.6° |
| α = 60.728 (1)° | µ = 0.36 mm−1 |
| β = 80.340 (1)° | T = 293 K |
| γ = 65.416 (1)° | Block, colourless |
| V = 731.3 (1) Å3 | 0.41 × 0.22 × 0.18 mm |
| Siemens SMART 1000 CCD area-detector diffractometer | 2529 independent reflections |
| Radiation source: fine-focus sealed tube | 2246 reflections with I > 2σ(I) |
| graphite | Rint = 0.010 |
| Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.3° |
| ω scans | h = −9→10 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→12 |
| Tmin = 0.865, Tmax = 0.938 | l = −12→12 |
| 3810 measured reflections |
| 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.143 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0806P)2 + 0.357P] where P = (Fo2 + 2Fc2)/3 |
| 2529 reflections | (Δ/σ)max < 0.001 |
| 172 parameters | Δρmax = 0.51 e Å−3 |
| 0 restraints | Δρmin = −0.38 e Å−3 |
| C11H15N5OS2 | γ = 65.416 (1)° |
| Mr = 297.40 | V = 731.3 (1) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.9723 (8) Å | Mo Kα radiation |
| b = 10.1103 (8) Å | µ = 0.36 mm−1 |
| c = 10.1734 (8) Å | T = 293 K |
| α = 60.728 (1)° | 0.41 × 0.22 × 0.18 mm |
| β = 80.340 (1)° |
| Siemens SMART 1000 CCD area-detector diffractometer | 2529 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2246 reflections with I > 2σ(I) |
| Tmin = 0.865, Tmax = 0.938 | Rint = 0.010 |
| 3810 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
| wR(F2) = 0.143 | Δρmax = 0.51 e Å−3 |
| S = 1.05 | Δρmin = −0.38 e Å−3 |
| 2529 reflections | Absolute structure: ? |
| 172 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| N1 | 0.5556 (3) | 0.4597 (3) | 0.7067 (3) | 0.0680 (7) | |
| N2 | 0.6886 (3) | 0.4050 (3) | 0.7986 (3) | 0.0670 (6) | |
| N3 | 0.2627 (3) | 0.8466 (3) | 0.4764 (2) | 0.0546 (5) | |
| N4 | 0.2154 (4) | 0.9710 (3) | 0.5103 (3) | 0.0718 (7) | |
| N5 | 0.2371 (4) | 1.0629 (3) | 0.2618 (3) | 0.0762 (7) | |
| O1 | 1.0413 (3) | 0.4947 (2) | 0.7133 (2) | 0.0746 (6) | |
| S1 | 0.49906 (8) | 0.68646 (9) | 0.77341 (9) | 0.0627 (3) | |
| S2 | 0.81659 (9) | 0.48127 (9) | 0.96116 (8) | 0.0609 (2) | |
| C1 | 0.6733 (3) | 0.5099 (3) | 0.8425 (3) | 0.0508 (6) | |
| C2 | 0.4489 (3) | 0.6004 (3) | 0.6854 (3) | 0.0548 (6) | |
| C3 | 0.2921 (4) | 0.6795 (4) | 0.5949 (4) | 0.0698 (8) | |
| H3A | 0.2954 | 0.6133 | 0.5496 | 0.084* | |
| H3B | 0.2013 | 0.6817 | 0.6618 | 0.084* | |
| C4 | 0.2003 (4) | 1.0979 (3) | 0.3766 (3) | 0.0657 (7) | |
| H4 | 0.1665 | 1.2043 | 0.3630 | 0.079* | |
| C5 | 0.2751 (4) | 0.9038 (4) | 0.3298 (3) | 0.0695 (8) | |
| H5 | 0.3066 | 0.8398 | 0.2807 | 0.083* | |
| C6 | 0.9842 (3) | 0.3090 (3) | 0.9519 (3) | 0.0543 (6) | |
| H6A | 1.0658 | 0.2611 | 1.0311 | 0.065* | |
| H6B | 0.9439 | 0.2261 | 0.9711 | 0.065* | |
| C7 | 1.0658 (3) | 0.3532 (3) | 0.8017 (3) | 0.0501 (6) | |
| C8 | 1.1780 (4) | 0.2127 (3) | 0.7691 (3) | 0.0629 (7) | |
| C9 | 1.2994 (7) | 0.0845 (7) | 0.8962 (5) | 0.199 (4) | |
| H9A | 1.3660 | 0.1311 | 0.9096 | 0.298* | |
| H9B | 1.3679 | −0.0042 | 0.8744 | 0.298* | |
| H9C | 1.2430 | 0.0437 | 0.9868 | 0.298* | |
| C10 | 1.2626 (5) | 0.2749 (5) | 0.6225 (4) | 0.0910 (11) | |
| H10A | 1.3325 | 0.3208 | 0.6317 | 0.136* | |
| H10B | 1.1816 | 0.3581 | 0.5422 | 0.136* | |
| H10C | 1.3272 | 0.1853 | 0.6008 | 0.136* | |
| C11 | 1.0686 (7) | 0.1417 (8) | 0.7445 (8) | 0.154 (3) | |
| H11A | 1.1360 | 0.0522 | 0.7235 | 0.231* | |
| H11B | 0.9921 | 0.2261 | 0.6609 | 0.231* | |
| H11C | 1.0097 | 0.1028 | 0.8338 | 0.231* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0740 (15) | 0.0541 (13) | 0.0763 (16) | −0.0174 (12) | −0.0189 (12) | −0.0300 (12) |
| N2 | 0.0678 (14) | 0.0555 (13) | 0.0776 (16) | −0.0112 (11) | −0.0206 (12) | −0.0341 (12) |
| N3 | 0.0551 (12) | 0.0475 (11) | 0.0590 (13) | −0.0186 (9) | −0.0090 (10) | −0.0209 (10) |
| N4 | 0.0947 (18) | 0.0605 (14) | 0.0618 (14) | −0.0268 (13) | 0.0001 (13) | −0.0315 (12) |
| N5 | 0.0926 (19) | 0.0611 (15) | 0.0560 (14) | −0.0159 (13) | −0.0140 (13) | −0.0200 (12) |
| O1 | 0.0788 (13) | 0.0500 (11) | 0.0763 (13) | −0.0282 (10) | 0.0123 (11) | −0.0161 (10) |
| S1 | 0.0575 (4) | 0.0554 (4) | 0.0780 (5) | −0.0157 (3) | −0.0043 (3) | −0.0359 (4) |
| S2 | 0.0656 (4) | 0.0655 (5) | 0.0606 (4) | −0.0234 (3) | −0.0027 (3) | −0.0359 (4) |
| C1 | 0.0536 (13) | 0.0487 (13) | 0.0494 (13) | −0.0200 (11) | 0.0021 (11) | −0.0222 (11) |
| C2 | 0.0572 (14) | 0.0470 (14) | 0.0568 (14) | −0.0238 (12) | −0.0020 (11) | −0.0175 (11) |
| C3 | 0.0673 (17) | 0.0545 (15) | 0.0793 (19) | −0.0301 (14) | −0.0174 (15) | −0.0138 (14) |
| C4 | 0.0773 (18) | 0.0486 (15) | 0.0634 (17) | −0.0160 (13) | −0.0089 (14) | −0.0239 (13) |
| C5 | 0.0795 (19) | 0.0606 (17) | 0.0645 (18) | −0.0124 (14) | −0.0127 (14) | −0.0336 (15) |
| C6 | 0.0585 (14) | 0.0493 (13) | 0.0493 (14) | −0.0200 (11) | −0.0091 (11) | −0.0161 (11) |
| C7 | 0.0472 (12) | 0.0462 (13) | 0.0537 (14) | −0.0198 (10) | −0.0097 (10) | −0.0162 (11) |
| C8 | 0.0658 (16) | 0.0536 (15) | 0.0588 (16) | −0.0192 (13) | 0.0017 (13) | −0.0216 (13) |
| C9 | 0.181 (6) | 0.165 (5) | 0.085 (3) | 0.104 (5) | −0.051 (3) | −0.063 (3) |
| C10 | 0.095 (3) | 0.095 (3) | 0.082 (2) | −0.037 (2) | 0.021 (2) | −0.046 (2) |
| C11 | 0.170 (5) | 0.186 (5) | 0.237 (7) | −0.129 (5) | 0.117 (5) | −0.176 (6) |
| N1—C2 | 1.274 (3) | C5—H5 | 0.9300 |
| N1—N2 | 1.387 (3) | C6—C7 | 1.516 (4) |
| N2—C1 | 1.290 (3) | C6—H6A | 0.9700 |
| N3—C5 | 1.313 (4) | C6—H6B | 0.9700 |
| N3—N4 | 1.347 (3) | C7—C8 | 1.517 (4) |
| N3—C3 | 1.456 (3) | C8—C9 | 1.482 (5) |
| N4—C4 | 1.314 (4) | C8—C10 | 1.515 (4) |
| N5—C5 | 1.310 (4) | C8—C11 | 1.544 (5) |
| N5—C4 | 1.332 (4) | C9—H9A | 0.9600 |
| O1—C7 | 1.205 (3) | C9—H9B | 0.9600 |
| S1—C1 | 1.715 (3) | C9—H9C | 0.9600 |
| S1—C2 | 1.728 (3) | C10—H10A | 0.9600 |
| S2—C1 | 1.751 (3) | C10—H10B | 0.9600 |
| S2—C6 | 1.799 (3) | C10—H10C | 0.9600 |
| C2—C3 | 1.498 (4) | C11—H11A | 0.9600 |
| C3—H3A | 0.9700 | C11—H11B | 0.9600 |
| C3—H3B | 0.9700 | C11—H11C | 0.9600 |
| C4—H4 | 0.9300 | ||
| C2—N1—N2 | 113.0 (2) | C7—C6—H6B | 108.8 |
| C1—N2—N1 | 111.5 (2) | S2—C6—H6B | 108.8 |
| C5—N3—N4 | 109.3 (2) | H6A—C6—H6B | 107.7 |
| C5—N3—C3 | 130.1 (3) | O1—C7—C6 | 120.5 (2) |
| N4—N3—C3 | 120.6 (2) | O1—C7—C8 | 122.2 (2) |
| C4—N4—N3 | 102.1 (2) | C6—C7—C8 | 117.3 (2) |
| C5—N5—C4 | 102.3 (2) | C9—C8—C10 | 111.0 (4) |
| C1—S1—C2 | 86.46 (12) | C9—C8—C7 | 110.6 (3) |
| C1—S2—C6 | 98.80 (12) | C10—C8—C7 | 110.9 (2) |
| N2—C1—S1 | 114.8 (2) | C9—C8—C11 | 110.8 (5) |
| N2—C1—S2 | 124.2 (2) | C10—C8—C11 | 106.0 (3) |
| S1—C1—S2 | 121.01 (15) | C7—C8—C11 | 107.3 (3) |
| N1—C2—C3 | 121.9 (3) | C8—C9—H9A | 109.5 |
| N1—C2—S1 | 114.2 (2) | C8—C9—H9B | 109.5 |
| C3—C2—S1 | 123.9 (2) | H9A—C9—H9B | 109.5 |
| N3—C3—C2 | 112.9 (2) | C8—C9—H9C | 109.5 |
| N3—C3—H3A | 109.0 | H9A—C9—H9C | 109.5 |
| C2—C3—H3A | 109.0 | H9B—C9—H9C | 109.5 |
| N3—C3—H3B | 109.0 | C8—C10—H10A | 109.5 |
| C2—C3—H3B | 109.0 | C8—C10—H10B | 109.5 |
| H3A—C3—H3B | 107.8 | H10A—C10—H10B | 109.5 |
| N4—C4—N5 | 115.0 (3) | C8—C10—H10C | 109.5 |
| N4—C4—H4 | 122.5 | H10A—C10—H10C | 109.5 |
| N5—C4—H4 | 122.5 | H10B—C10—H10C | 109.5 |
| N5—C5—N3 | 111.1 (3) | C8—C11—H11A | 109.5 |
| N5—C5—H5 | 124.4 | C8—C11—H11B | 109.5 |
| N3—C5—H5 | 124.4 | H11A—C11—H11B | 109.5 |
| C7—C6—S2 | 113.74 (17) | C8—C11—H11C | 109.5 |
| C7—C6—H6A | 108.8 | H11A—C11—H11C | 109.5 |
| S2—C6—H6A | 108.8 | H11B—C11—H11C | 109.5 |
| C2—N1—N2—C1 | 0.3 (4) | S1—C2—C3—N3 | 53.9 (4) |
| C5—N3—N4—C4 | 0.9 (3) | N3—N4—C4—N5 | −1.1 (4) |
| C3—N3—N4—C4 | −179.3 (2) | C5—N5—C4—N4 | 0.9 (4) |
| N1—N2—C1—S1 | −1.4 (3) | C4—N5—C5—N3 | −0.3 (4) |
| N1—N2—C1—S2 | 179.3 (2) | N4—N3—C5—N5 | −0.4 (4) |
| C2—S1—C1—N2 | 1.6 (2) | C3—N3—C5—N5 | 179.8 (3) |
| C2—S1—C1—S2 | −179.13 (18) | C1—S2—C6—C7 | 71.9 (2) |
| C6—S2—C1—N2 | 13.2 (3) | S2—C6—C7—O1 | 15.0 (3) |
| C6—S2—C1—S1 | −166.03 (16) | S2—C6—C7—C8 | −165.12 (19) |
| N2—N1—C2—C3 | −177.4 (3) | O1—C7—C8—C9 | 129.1 (4) |
| N2—N1—C2—S1 | 0.9 (3) | C6—C7—C8—C9 | −50.8 (5) |
| C1—S1—C2—N1 | −1.4 (2) | O1—C7—C8—C10 | 5.4 (4) |
| C1—S1—C2—C3 | 176.9 (2) | C6—C7—C8—C10 | −174.5 (2) |
| C5—N3—C3—C2 | 105.8 (3) | O1—C7—C8—C11 | −109.9 (4) |
| N4—N3—C3—C2 | −74.1 (4) | C6—C7—C8—C11 | 70.2 (4) |
| N1—C2—C3—N3 | −127.9 (3) |
This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Z2006B01 and Y2006B07).
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Recently, we have reported the structure of 1-(2,4-dichlorophenyl)-2-[5-(1H-1,2,4- triazol-1-ylmethyl)-1,3,4-thiadiazol-2-ylsulfanyl] ethanone (Wei et al., 2007). As part of our ongoing investigation of biological properties of 1,2,4-triazole and 1,3,4-thiadiazole derivatives, the title compound, (I), was synthesized; its crystal structure is reported here.
The bond lengths and angles are comparable with those of the above mentioned related compound, reported by Wei et al. (2007). The whole molecule is non-planar with a dihedral angle of 59.9 (2)° between the thiadiazole (C1/C2/N1/N2/S1) and triazole (N3—N5/C4/C5) rings. The S2—C6—C7—C8—C10 atoms form approximately planar zigzag chain, which makes a dihedral angle of 74.6 (1)° with the thiadiazole ring.