Buy article online - an online subscription or single-article purchase is required to access this article.
organic compounds
In the title compound, C13H11N5OS, molecules are linked into centrosymmetric dimers through intermolecular N—HO 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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.107
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
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. |
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