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In the title compound, C13H15N7S2, the two triazole rings are twisted away from the central pyridine ring by 11.7 (2) and 41.8 (1)°. Inversion-related mol­ecules are linked by N—H...S hydrogen bonds, forming dimers which are linked into a chain by N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015984/ci2060sup1.cif
Contains datablocks 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015984/ci20602sup2.hkl
Contains datablock 2

CCDC reference: 610734

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.055
  • wR factor = 0.163
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.110 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 3 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-RED32 (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) and PLATON (Spek, 2003).

5,5'-Pyridine-2,6-diylbis[4-ethyl-2,4-dihydro-1,2,4-triazole-3(2H)-thione] top
Crystal data top
C13H15N7S2F(000) = 696
Mr = 333.46Dx = 1.463 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15851 reflections
a = 6.7330 (6) Åθ = 2.0–28.0°
b = 18.4906 (13) ŵ = 0.36 mm1
c = 12.3576 (12) ÅT = 296 K
β = 100.162 (8)°Prism, colourless
V = 1514.4 (2) Å30.46 × 0.32 × 0.21 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
3574 independent reflections
Radiation source: fine-focus sealed tube2126 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.110
Detector resolution: 6.67 pixels mm-1θmax = 28.0°, θmin = 2.0°
ω scansh = 88
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2424
Tmin = 0.875, Tmax = 0.931l = 1616
15631 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.0925P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
3574 reflectionsΔρmax = 0.43 e Å3
201 parametersΔρmin = 0.63 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (4)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C12A0.7092 (9)0.2253 (3)0.1608 (5)0.0593 (7)0.538 (4)
H12A0.69330.25230.22600.071*0.538 (4)
H12B0.82980.19570.17750.071*0.538 (4)
C13A0.7203 (9)0.2755 (3)0.0656 (4)0.0593 (7)0.538 (4)
H13A0.83510.30680.08400.089*0.538 (4)
H13B0.59950.30410.05050.089*0.538 (4)
H13C0.73330.24760.00170.089*0.538 (4)
C12B0.6071 (11)0.2475 (3)0.0870 (5)0.0593 (7)0.462 (4)
H12C0.63180.24530.01210.071*0.462 (4)
H12D0.51800.28790.09380.071*0.462 (4)
C13B0.7939 (11)0.2539 (4)0.1644 (5)0.0593 (7)0.462 (4)
H13D0.86270.29730.14940.089*0.462 (4)
H13E0.87770.21280.15760.089*0.462 (4)
H13F0.76550.25600.23780.089*0.462 (4)
C10.1574 (4)0.52020 (14)0.1886 (2)0.0530 (6)
C20.1663 (4)0.41173 (12)0.2652 (2)0.0453 (5)
C30.3669 (5)0.43138 (14)0.1092 (2)0.0565 (7)
H3A0.33140.45870.04150.068*
H3B0.35080.38040.09120.068*
C40.5809 (5)0.44602 (19)0.1584 (3)0.0766 (9)
H4A0.66640.43240.10730.115*
H4B0.61690.41850.22480.115*
H4C0.59770.49660.17490.115*
C50.2021 (4)0.33480 (13)0.2943 (2)0.0460 (6)
C60.1426 (4)0.31071 (14)0.3907 (2)0.0510 (6)
H60.08780.34270.43540.061*
C70.1664 (5)0.23884 (14)0.4184 (2)0.0538 (7)
H70.12810.22140.48230.065*
C80.2482 (4)0.19291 (14)0.3496 (2)0.0511 (6)
H80.26850.14420.36700.061*
C90.2990 (4)0.22071 (13)0.2550 (2)0.0460 (6)
C100.3667 (4)0.16960 (12)0.17762 (19)0.0448 (6)
C110.5338 (4)0.11560 (13)0.0617 (2)0.0514 (6)
N10.2306 (3)0.45113 (11)0.18439 (16)0.0478 (5)
N20.0529 (4)0.51659 (12)0.27087 (19)0.0599 (6)
H20.01100.55300.29130.072*
N30.0560 (4)0.45050 (12)0.31958 (19)0.0568 (6)
N40.2805 (3)0.29102 (11)0.22639 (17)0.0483 (5)
N50.5193 (4)0.17756 (12)0.1196 (2)0.0674 (7)
N60.2812 (3)0.10695 (10)0.15842 (16)0.0463 (5)
N70.3872 (3)0.07463 (10)0.08689 (16)0.0472 (5)
H7A0.36130.03190.06080.057*
S10.19464 (16)0.59157 (4)0.11263 (7)0.0740 (3)
S20.69633 (14)0.09592 (4)0.02218 (8)0.0762 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C12A0.059 (2)0.0438 (17)0.0771 (17)0.0104 (12)0.0169 (15)0.0038 (14)
C13A0.059 (2)0.0438 (17)0.0771 (17)0.0104 (12)0.0169 (15)0.0038 (14)
C12B0.059 (2)0.0438 (17)0.0771 (17)0.0104 (12)0.0169 (15)0.0038 (14)
C13B0.059 (2)0.0438 (17)0.0771 (17)0.0104 (12)0.0169 (15)0.0038 (14)
C10.0576 (17)0.0432 (14)0.0603 (14)0.0069 (11)0.0164 (12)0.0035 (11)
C20.0486 (15)0.0364 (12)0.0543 (13)0.0014 (10)0.0183 (11)0.0055 (9)
C30.081 (2)0.0382 (13)0.0579 (14)0.0006 (12)0.0344 (14)0.0051 (11)
C40.070 (2)0.075 (2)0.095 (2)0.0014 (16)0.0434 (18)0.0103 (17)
C50.0491 (15)0.0376 (12)0.0545 (13)0.0046 (10)0.0181 (11)0.0071 (10)
C60.0569 (17)0.0469 (14)0.0537 (13)0.0044 (11)0.0220 (12)0.0092 (11)
C70.0649 (19)0.0475 (14)0.0539 (14)0.0033 (12)0.0243 (12)0.0012 (11)
C80.0577 (17)0.0405 (13)0.0590 (13)0.0027 (11)0.0211 (12)0.0017 (11)
C90.0491 (16)0.0354 (12)0.0570 (13)0.0041 (10)0.0190 (11)0.0051 (10)
C100.0519 (15)0.0310 (11)0.0562 (13)0.0028 (10)0.0225 (11)0.0020 (9)
C110.0580 (17)0.0351 (12)0.0664 (15)0.0027 (11)0.0255 (12)0.0032 (10)
N10.0567 (14)0.0360 (10)0.0543 (11)0.0026 (9)0.0197 (10)0.0055 (8)
N20.0700 (17)0.0424 (12)0.0749 (14)0.0111 (10)0.0339 (12)0.0006 (10)
N30.0654 (16)0.0416 (11)0.0705 (13)0.0039 (10)0.0318 (11)0.0018 (10)
N40.0562 (14)0.0342 (10)0.0602 (11)0.0034 (9)0.0255 (10)0.0067 (8)
N50.0762 (18)0.0404 (12)0.1003 (17)0.0203 (11)0.0561 (14)0.0250 (11)
N60.0548 (14)0.0335 (10)0.0552 (11)0.0040 (8)0.0229 (9)0.0039 (8)
N70.0563 (14)0.0316 (9)0.0589 (12)0.0045 (8)0.0243 (10)0.0083 (8)
S10.1018 (7)0.0469 (4)0.0822 (5)0.0174 (4)0.0407 (5)0.0122 (3)
S20.0892 (6)0.0470 (4)0.1101 (6)0.0153 (4)0.0666 (5)0.0237 (4)
Geometric parameters (Å, º) top
C12A—C13A1.512 (8)C3—H3B0.97
C12A—N51.563 (6)C4—H4A0.96
C12A—H12A0.97C4—H4B0.96
C12A—H12B0.97C4—H4C0.96
C13A—H13A0.96C5—N41.340 (3)
C13A—H13B0.96C5—C61.394 (3)
C13A—H13C0.96C6—C71.375 (4)
C12B—C13B1.444 (10)C6—H60.93
C12B—N51.507 (6)C7—C81.383 (4)
C12B—H12C0.97C7—H70.93
C12B—H12D0.97C8—C91.374 (3)
C13B—H13D0.96C8—H80.93
C13B—H13E0.96C9—N41.347 (3)
C13B—H13F0.96C9—C101.473 (3)
C1—N21.337 (4)C10—N61.297 (3)
C1—N11.373 (3)C10—N51.361 (3)
C1—S11.664 (3)C11—N71.324 (3)
C2—N31.301 (3)C11—N51.363 (3)
C2—N11.367 (3)C11—S21.675 (3)
C2—C51.477 (3)N2—N31.361 (3)
C3—N11.463 (3)N2—H20.86
C3—C41.487 (5)N6—N71.368 (3)
C3—H3A0.97N7—H7A0.86
C13A—C12A—N5104.1 (4)H4A—C4—H4C109.5
C13A—C12A—H12A110.9H4B—C4—H4C109.5
N5—C12A—H12A110.9N4—C5—C6123.1 (2)
C13A—C12A—H12B110.9N4—C5—C2119.6 (2)
N5—C12A—H12B110.9C6—C5—C2117.2 (2)
H12A—C12A—H12B109.0C7—C6—C5118.9 (2)
C12A—C13A—H13A109.5C7—C6—H6120.5
C12A—C13A—H13B109.5C5—C6—H6120.5
H13A—C13A—H13B109.5C6—C7—C8118.8 (2)
C12A—C13A—H13C109.5C6—C7—H7120.6
H13A—C13A—H13C109.5C8—C7—H7120.6
H13B—C13A—H13C109.5C9—C8—C7118.6 (2)
C13B—C12B—N5103.3 (5)C9—C8—H8120.7
C13B—C12B—H12C111.1C7—C8—H8120.7
N5—C12B—H12C111.1N4—C9—C8124.0 (2)
C13B—C12B—H12D111.1N4—C9—C10118.3 (2)
N5—C12B—H12D111.1C8—C9—C10117.7 (2)
H12C—C12B—H12D109.1N6—C10—N5110.6 (2)
C12B—C13B—H13D109.5N6—C10—C9120.9 (2)
C12B—C13B—H13E109.5N5—C10—C9128.4 (2)
H13D—C13B—H13E109.5N7—C11—N5103.4 (2)
C12B—C13B—H13F109.5N7—C11—S2128.07 (19)
H13D—C13B—H13F109.5N5—C11—S2128.5 (2)
H13E—C13B—H13F109.5C2—N1—C1107.8 (2)
N2—C1—N1102.9 (2)C2—N1—C3130.3 (2)
N2—C1—S1128.4 (2)C1—N1—C3121.7 (2)
N1—C1—S1128.7 (2)C1—N2—N3114.3 (2)
N3—C2—N1111.5 (2)C1—N2—H2122.8
N3—C2—C5119.2 (2)N3—N2—H2122.8
N1—C2—C5129.2 (2)C2—N3—N2103.4 (2)
N1—C3—C4111.5 (2)C5—N4—C9116.6 (2)
N1—C3—H3A109.3C10—N5—C11108.4 (2)
C4—C3—H3A109.3C10—N5—C12B127.0 (3)
N1—C3—H3B109.3C11—N5—C12B120.9 (3)
C4—C3—H3B109.3C10—N5—C12A122.7 (3)
H3A—C3—H3B108.0C11—N5—C12A121.0 (3)
C3—C4—H4A109.5C10—N6—N7104.1 (2)
C3—C4—H4B109.5C11—N7—N6113.41 (19)
H4A—C4—H4B109.5C11—N7—H7A123.3
C3—C4—H4C109.5N6—N7—H7A123.3
N3—C2—C5—N4166.9 (3)C1—N2—N3—C20.2 (3)
N1—C2—C5—N411.7 (4)C6—C5—N4—C90.5 (4)
N3—C2—C5—C610.2 (4)C2—C5—N4—C9176.5 (2)
N1—C2—C5—C6171.2 (3)C8—C9—N4—C51.9 (4)
N4—C5—C6—C70.5 (4)C10—C9—N4—C5174.4 (2)
C2—C5—C6—C7177.6 (2)N6—C10—N5—C111.2 (3)
C5—C6—C7—C80.1 (4)C9—C10—N5—C11177.6 (3)
C6—C7—C8—C91.2 (4)N6—C10—N5—C12B157.2 (4)
C7—C8—C9—N42.4 (4)C9—C10—N5—C12B24.1 (6)
C7—C8—C9—C10174.0 (2)N6—C10—N5—C12A150.4 (3)
N4—C9—C10—N6137.1 (3)C9—C10—N5—C12A28.3 (5)
C8—C9—C10—N639.5 (4)N7—C11—N5—C101.0 (3)
N4—C9—C10—N544.3 (4)S2—C11—N5—C10179.5 (2)
C8—C9—C10—N5139.1 (3)N7—C11—N5—C12B159.0 (4)
N3—C2—N1—C10.7 (3)S2—C11—N5—C12B20.6 (5)
C5—C2—N1—C1179.4 (3)N7—C11—N5—C12A150.8 (3)
N3—C2—N1—C3175.4 (3)S2—C11—N5—C12A29.6 (5)
C5—C2—N1—C35.9 (4)C13B—C12B—N5—C10102.8 (5)
N2—C1—N1—C20.7 (3)C13B—C12B—N5—C11101.3 (5)
S1—C1—N1—C2177.8 (2)C13B—C12B—N5—C12A2.4 (5)
N2—C1—N1—C3176.0 (2)C13A—C12A—N5—C10126.9 (4)
S1—C1—N1—C32.5 (4)C13A—C12A—N5—C1187.6 (5)
C4—C3—N1—C287.7 (3)C13A—C12A—N5—C12B15.9 (5)
C4—C3—N1—C186.5 (3)N5—C10—N6—N70.8 (3)
N1—C1—N2—N30.5 (3)C9—C10—N6—N7178.0 (2)
S1—C1—N2—N3177.9 (2)N5—C11—N7—N60.5 (3)
N1—C2—N3—N20.3 (3)S2—C11—N7—N6180.0 (2)
C5—C2—N3—N2179.2 (2)C10—N6—N7—C110.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N6i0.862.263.051 (3)154
N7—H7A···S2ii0.862.433.278 (2)169
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z.
 

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