
In the title compound, C13H11N5OS, molecules are linked into centrosymmetric dimers through intermolecular N—H
O hydrogen bonds.

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023981/bh2022sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023981/bh2022Isup2.hkl |
CCDC reference: 613576
Computing details top
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
4-(2-Pyridylmethyleneamino)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one top
Crystal data top
C13H11N5OS | F(000) = 592 |
Mr = 285.33 | Dx = 1.449 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 15109 reflections |
a = 5.6726 (4) Å | θ = 1.6–27.6° |
b = 18.3669 (11) Å | µ = 0.25 mm−1 |
c = 12.5690 (9) Å | T = 293 K |
β = 92.651 (6)° | Prism, colourless |
V = 1308.14 (15) Å3 | 0.48 × 0.20 × 0.02 mm |
Z = 4 |
Data collection top
Stoe IPDS-II diffractometer | 2564 independent reflections |
Radiation source: fine-focus sealed tube | 1785 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
rotation method scans | h = −6→6 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −20→22 |
Tmin = 0.910, Tmax = 0.988 | l = −15→15 |
13756 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0622P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
2564 reflections | Δρmax = 0.28 e Å−3 |
182 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0091 (19) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.0296 (5) | 0.35978 (14) | 0.7881 (2) | 0.0443 (7) | |
H1 | −0.0987 | 0.3858 | 0.7592 | 0.053* | |
C2 | 0.2179 (4) | 0.34060 (13) | 0.73282 (19) | 0.0366 (6) | |
H2 | 0.2323 | 0.3521 | 0.6614 | 0.044* | |
C3 | 0.3951 (4) | 0.30057 (11) | 0.79478 (16) | 0.0277 (5) | |
H3 | 0.5359 | 0.2833 | 0.7693 | 0.033* | |
C4 | 0.3223 (4) | 0.29174 (12) | 0.89947 (17) | 0.0295 (5) | |
C5 | 0.4456 (4) | 0.24959 (12) | 0.98867 (17) | 0.0312 (5) | |
H5A | 0.6122 | 0.2456 | 0.9755 | 0.037* | |
H5B | 0.4304 | 0.2755 | 1.0553 | 0.037* | |
C6 | 0.3429 (4) | 0.17565 (12) | 0.99748 (16) | 0.0269 (5) | |
C7 | 0.2684 (4) | 0.05795 (12) | 0.96098 (16) | 0.0267 (5) | |
C8 | 0.6554 (4) | 0.06498 (12) | 0.82050 (16) | 0.0290 (5) | |
H8 | 0.5634 | 0.0232 | 0.8244 | 0.035* | |
C9 | 0.8568 (4) | 0.06647 (12) | 0.75151 (16) | 0.0279 (5) | |
C10 | 1.0020 (4) | 0.12652 (13) | 0.74141 (17) | 0.0299 (5) | |
H10 | 0.9747 | 0.1693 | 0.7784 | 0.036* | |
C11 | 1.1888 (4) | 0.12105 (14) | 0.67478 (18) | 0.0339 (6) | |
H11 | 1.2902 | 0.1602 | 0.6663 | 0.041* | |
C12 | 1.2224 (4) | 0.05663 (14) | 0.62116 (18) | 0.0353 (6) | |
H12 | 1.3460 | 0.0517 | 0.5756 | 0.042* | |
C13 | 1.0699 (4) | −0.00028 (13) | 0.63636 (18) | 0.0342 (6) | |
H13 | 1.0952 | −0.0437 | 0.6005 | 0.041* | |
N1 | 0.1656 (4) | 0.15916 (10) | 1.05344 (14) | 0.0318 (4) | |
N2 | 0.1234 (3) | 0.08606 (10) | 1.03169 (14) | 0.0301 (4) | |
H6 | 0.0151 | 0.0612 | 1.0607 | 0.036* | |
N3 | 0.4152 (3) | 0.11639 (10) | 0.93933 (13) | 0.0257 (4) | |
N4 | 0.6065 (3) | 0.12114 (10) | 0.87529 (13) | 0.0268 (4) | |
N5 | 0.8882 (4) | 0.00324 (11) | 0.69947 (14) | 0.0322 (5) | |
O1 | 0.2715 (3) | −0.00434 (8) | 0.92330 (12) | 0.0306 (4) | |
S1 | 0.05312 (12) | 0.33106 (4) | 0.91681 (5) | 0.0437 (2) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0366 (15) | 0.0327 (14) | 0.0629 (17) | −0.0015 (12) | −0.0055 (13) | 0.0119 (12) |
C2 | 0.0395 (15) | 0.0320 (13) | 0.0378 (12) | −0.0091 (11) | −0.0025 (11) | 0.0038 (10) |
C3 | 0.0316 (13) | 0.0212 (11) | 0.0298 (11) | −0.0072 (10) | −0.0042 (9) | −0.0005 (9) |
C4 | 0.0304 (13) | 0.0226 (12) | 0.0358 (11) | −0.0052 (10) | 0.0042 (9) | −0.0021 (9) |
C5 | 0.0357 (13) | 0.0265 (12) | 0.0313 (11) | −0.0062 (10) | −0.0003 (9) | −0.0031 (9) |
C6 | 0.0304 (12) | 0.0252 (12) | 0.0248 (10) | −0.0015 (10) | −0.0025 (9) | 0.0004 (8) |
C7 | 0.0278 (12) | 0.0255 (11) | 0.0264 (10) | −0.0023 (9) | −0.0029 (9) | 0.0038 (9) |
C8 | 0.0301 (13) | 0.0264 (11) | 0.0302 (11) | −0.0023 (10) | −0.0015 (9) | 0.0050 (9) |
C9 | 0.0282 (12) | 0.0277 (12) | 0.0272 (10) | 0.0021 (10) | −0.0040 (9) | 0.0041 (9) |
C10 | 0.0301 (13) | 0.0276 (12) | 0.0318 (11) | 0.0010 (10) | −0.0022 (9) | 0.0043 (9) |
C11 | 0.0306 (13) | 0.0359 (13) | 0.0351 (12) | −0.0025 (11) | −0.0016 (10) | 0.0097 (10) |
C12 | 0.0333 (14) | 0.0417 (15) | 0.0311 (11) | 0.0046 (11) | 0.0051 (10) | 0.0041 (10) |
C13 | 0.0369 (14) | 0.0336 (13) | 0.0322 (11) | 0.0049 (11) | 0.0014 (10) | −0.0022 (10) |
N1 | 0.0372 (11) | 0.0268 (10) | 0.0316 (9) | −0.0048 (9) | 0.0023 (8) | −0.0015 (8) |
N2 | 0.0331 (11) | 0.0248 (10) | 0.0326 (10) | −0.0060 (9) | 0.0056 (8) | 0.0013 (8) |
N3 | 0.0265 (10) | 0.0251 (10) | 0.0255 (9) | −0.0031 (8) | 0.0002 (7) | 0.0014 (7) |
N4 | 0.0258 (10) | 0.0284 (10) | 0.0260 (9) | −0.0020 (8) | −0.0012 (7) | 0.0039 (8) |
N5 | 0.0337 (12) | 0.0299 (11) | 0.0327 (10) | −0.0002 (9) | −0.0015 (8) | −0.0016 (8) |
O1 | 0.0326 (9) | 0.0238 (8) | 0.0356 (8) | −0.0039 (7) | 0.0022 (7) | 0.0014 (7) |
S1 | 0.0386 (4) | 0.0374 (4) | 0.0559 (4) | 0.0021 (3) | 0.0118 (3) | 0.0019 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.348 (4) | C8—N4 | 1.278 (3) |
C1—S1 | 1.701 (3) | C8—C9 | 1.466 (3) |
C1—H1 | 0.9300 | C8—H8 | 0.9300 |
C2—C3 | 1.444 (3) | C9—N5 | 1.349 (3) |
C2—H2 | 0.9300 | C9—C10 | 1.386 (3) |
C3—C4 | 1.407 (3) | C10—C11 | 1.385 (3) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.507 (3) | C11—C12 | 1.379 (4) |
C4—S1 | 1.712 (2) | C11—H11 | 0.9300 |
C5—C6 | 1.484 (3) | C12—C13 | 1.376 (4) |
C5—H5A | 0.9700 | C12—H12 | 0.9300 |
C5—H5B | 0.9700 | C13—N5 | 1.331 (3) |
C6—N1 | 1.290 (3) | C13—H13 | 0.9300 |
C6—N3 | 1.384 (3) | N1—N2 | 1.389 (3) |
C7—O1 | 1.239 (3) | N2—H6 | 0.8600 |
C7—N2 | 1.341 (3) | N3—N4 | 1.384 (3) |
C7—N3 | 1.393 (3) | ||
C2—C1—S1 | 112.3 (2) | C9—C8—H8 | 120.1 |
C2—C1—H1 | 123.8 | N5—C9—C10 | 123.3 (2) |
S1—C1—H1 | 123.8 | N5—C9—C8 | 113.3 (2) |
C1—C2—C3 | 113.8 (2) | C10—C9—C8 | 123.5 (2) |
C1—C2—H2 | 123.1 | C11—C10—C9 | 118.2 (2) |
C3—C2—H2 | 123.1 | C11—C10—H10 | 120.9 |
C4—C3—C2 | 109.6 (2) | C9—C10—H10 | 120.9 |
C4—C3—H3 | 125.2 | C12—C11—C10 | 119.0 (2) |
C2—C3—H3 | 125.2 | C12—C11—H11 | 120.5 |
C3—C4—C5 | 127.5 (2) | C10—C11—H11 | 120.5 |
C3—C4—S1 | 111.87 (17) | C13—C12—C11 | 118.8 (2) |
C5—C4—S1 | 120.50 (17) | C13—C12—H12 | 120.6 |
C6—C5—C4 | 110.82 (18) | C11—C12—H12 | 120.6 |
C6—C5—H5A | 109.5 | N5—C13—C12 | 123.7 (2) |
C4—C5—H5A | 109.5 | N5—C13—H13 | 118.1 |
C6—C5—H5B | 109.5 | C12—C13—H13 | 118.1 |
C4—C5—H5B | 109.5 | C6—N1—N2 | 104.55 (18) |
H5A—C5—H5B | 108.1 | C7—N2—N1 | 113.41 (18) |
N1—C6—N3 | 111.16 (19) | C7—N2—H6 | 123.3 |
N1—C6—C5 | 125.1 (2) | N1—N2—H6 | 123.3 |
N3—C6—C5 | 123.6 (2) | N4—N3—C6 | 121.16 (18) |
O1—C7—N2 | 129.0 (2) | N4—N3—C7 | 130.87 (18) |
O1—C7—N3 | 128.1 (2) | C6—N3—C7 | 107.96 (18) |
N2—C7—N3 | 102.89 (18) | C8—N4—N3 | 117.27 (19) |
N4—C8—C9 | 119.9 (2) | C13—N5—C9 | 117.0 (2) |
N4—C8—H8 | 120.1 | C1—S1—C4 | 92.36 (13) |
S1—C1—C2—C3 | −0.1 (3) | C6—N1—N2—C7 | −1.7 (2) |
C1—C2—C3—C4 | 0.1 (3) | N1—C6—N3—N4 | −178.51 (18) |
C2—C3—C4—C5 | 175.9 (2) | C5—C6—N3—N4 | 6.1 (3) |
C2—C3—C4—S1 | −0.1 (2) | N1—C6—N3—C7 | 0.3 (2) |
C3—C4—C5—C6 | −97.1 (3) | C5—C6—N3—C7 | −175.08 (19) |
S1—C4—C5—C6 | 78.6 (2) | O1—C7—N3—N4 | −3.0 (4) |
C4—C5—C6—N1 | −88.2 (3) | N2—C7—N3—N4 | 177.40 (19) |
C4—C5—C6—N3 | 86.5 (3) | O1—C7—N3—C6 | 178.4 (2) |
N4—C8—C9—N5 | 179.39 (19) | N2—C7—N3—C6 | −1.2 (2) |
N4—C8—C9—C10 | 0.0 (3) | C9—C8—N4—N3 | −179.68 (18) |
N5—C9—C10—C11 | −0.2 (3) | C6—N3—N4—C8 | −176.92 (19) |
C8—C9—C10—C11 | 179.1 (2) | C7—N3—N4—C8 | 4.6 (3) |
C9—C10—C11—C12 | 0.2 (3) | C12—C13—N5—C9 | −0.7 (3) |
C10—C11—C12—C13 | −0.5 (3) | C10—C9—N5—C13 | 0.4 (3) |
C11—C12—C13—N5 | 0.8 (4) | C8—C9—N5—C13 | −178.98 (19) |
N3—C6—N1—N2 | 0.8 (2) | C2—C1—S1—C4 | 0.0 (2) |
C5—C6—N1—N2 | 176.06 (19) | C3—C4—S1—C1 | 0.02 (18) |
O1—C7—N2—N1 | −177.8 (2) | C5—C4—S1—C1 | −176.32 (19) |
N3—C7—N2—N1 | 1.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H6···O1i | 0.86 | 1.95 | 2.777 (2) | 161 |
Symmetry code: (i) −x, −y, −z+2. |