organic compounds
3-Amino-1H-1,2,4-triazole-5(4H)-thione–4,4′-bipyridine (1/1)
aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and bKey Laboratory of Terahertz Optoelectronics, Ministry of Education, Department of Physics, Capital Normal University, Beijing 100048, People's Republic of China
*Correspondence e-mail: jinqh204@163.com
The title two-component molecular crystal, C10H8N2·C2H4N4S, was obtained unexpectedly by reaction of Zn(NO3)2·6H2O, NH4BF4 with 3-amino-1,2,4-triazole-5-thione (3-AMT) and 4,4′-bipyridine in water. The dihedral angle between the pyridine rings in the 4,4′-bipyridine molecule is 17.00 (13)°. In the crystal, N—H⋯N and N—H⋯S hydrogen bonds between the components lead to the formation of a three-dimensional network. Furthermore, the structure features face-to-face π–π stacking interactions between the 4,4′-bipyridine and triazole rings, with a centroid–centroid distance of 2.976 (2) Å.
Related literature
For background to the 3-amino-1,2,4-triazole-5-thione ligand, see: Hao et al. (2010); Ma et al. (2008); Rakova et al. (2003). For related structures, see: Deng et al. (2005); Downie et al. (1972).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812037671/ff2081sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037671/ff2081Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812037671/ff2081Isup3.cml
A mixture of 3-AMT (0.6 mmol), NaOH (0.6 mmol), NH4BF4 (0.6 mmol), Zn(NO3)2.6H2O (0.3 mmol), 4,4'-bipyridine (0.3 mmol) and water (10 mL) was placed in a Teflon-lined stainless steel vessel (20 mL) and heated at 150°C for 72 h and then cooled to room temperature at a rate of 5°C/h.The filtrate was evaporated slowly at room temperature for 2 weeks to yield yellow crystalline products.
The final refinements were performed by full matrix least-squares methods with anisotropic thermal parameters for non-hydrogen atoms on F2. All hydrogen atoms were located in the calculated sites and included in the final
in the riding model approximation with displacement parameters derived from the parent atoms to which they were bonded (Uiso(H) = 1.2Ueq).Supramolecular compounds have received much attention due to their structural diversities and potential applications as new materials. The ligand 3-amino-1,2,4-triazole-5-thione(3-AMT), with one –SH, one –NH2 group and three potential coordination nitrogen atoms of triazole, is excellent in building metal-organic supramolecular structures (Hao et al., 2010; Ma et al., 2008; Rakova et al., 2003). Moreover, its nitrogen atom and sulfur atom may be involved in hydrogen bonding (Deng et al., 2005; Downie et al., 1972).
The title compound was unexpectedly obtained in the course of synthesizing 3-AMT-Zn(II) complexes. The molecular structure of the title compound is shown in Fig.1. The π-π stacking interactions between 4,4'-bipyridine and triazole ring, with the centroid-centroid distance of 2.976 (2) Å.
of C2H2N4S.C10H8N2 has been determined at room temperature. The compound has the P2(1)/c, with a = 13.5151 (12), b = 6.9680 (5), c = 16.5529 (14) Å and beta = 122.385 (2)°. The hydrogen bonds are formed between the N—H donors of 3-AMT and the nitrogen atoms from 4,4'-bipyridine and 3-AMT, and the atoms N6, N5 and N3 act as acceptors with d(N1···O6) = 2.828 (3) Å, d(N2···N5) = 2.829 (3) Å, d(N4···N3) = 3.151 (3) Å, N1—H1···N6 =171°, N2—H2···N5 =163° and N4—H4A···N3 =159°, which are just similar to the corresponding distances and angles in the compound of C10H8N2.2C2H3N3S2 (Deng et al., 2005). Intermolecular hydrogen bonds N—H···N and N—H···S between the components lead to the formation of a three-dimensional network (Fig.2). Furthermore, the structure is stabilized by the face to faceFor background to the 3-amino-1,2,4-triazole-5-thione ligand, see: Hao et al. (2010); Ma et al. (2008); Rakova et al. (2003). For related structures, see: Deng et al. (2005); Downie et al. (1972).
Data collection: SMART (Bruker, 2007); cell
SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C10H8N2·C2H4N4S | F(000) = 568 |
Mr = 272.34 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.5151 (12) Å | Cell parameters from 2519 reflections |
b = 6.9680 (5) Å | θ = 2.9–27.9° |
c = 16.5529 (14) Å | µ = 0.24 mm−1 |
β = 122.385 (2)° | T = 298 K |
V = 1316.39 (19) Å3 | Block, yellow |
Z = 4 | 0.40 × 0.30 × 0.21 mm |
Bruker SMART CCD area-detector diffractometer | 2315 independent reflections |
Radiation source: fine-focus sealed tube | 1725 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
phi and ω scans | θmax = 25.0°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −16→16 |
Tmin = 0.910, Tmax = 0.951 | k = −8→6 |
6507 measured reflections | l = −19→15 |
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)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0451P)2 + 0.5763P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
2315 reflections | Δρmax = 0.40 e Å−3 |
173 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.028 (2) |
C10H8N2·C2H4N4S | V = 1316.39 (19) Å3 |
Mr = 272.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.5151 (12) Å | µ = 0.24 mm−1 |
b = 6.9680 (5) Å | T = 298 K |
c = 16.5529 (14) Å | 0.40 × 0.30 × 0.21 mm |
β = 122.385 (2)° |
Bruker SMART CCD area-detector diffractometer | 2315 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 1725 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.951 | Rint = 0.034 |
6507 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.40 e Å−3 |
2315 reflections | Δρmin = −0.29 e Å−3 |
173 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 | ||
N1 | 0.54234 (15) | 0.3890 (3) | 0.81338 (12) | 0.0356 (5) | |
H1 | 0.4953 | 0.3948 | 0.7523 | 0.043* | |
N2 | 0.69266 (15) | 0.3516 (3) | 0.95219 (12) | 0.0377 (5) | |
H2 | 0.7632 | 0.3273 | 0.9982 | 0.045* | |
N3 | 0.60324 (16) | 0.3979 (3) | 0.96667 (13) | 0.0377 (5) | |
N4 | 0.40154 (16) | 0.4607 (3) | 0.85462 (14) | 0.0487 (6) | |
H4A | 0.3859 | 0.4756 | 0.8982 | 0.058* | |
H4B | 0.3469 | 0.4722 | 0.7953 | 0.058* | |
N5 | 1.08698 (16) | 0.6753 (3) | 0.87403 (13) | 0.0420 (5) | |
N6 | 0.62173 (17) | 0.6303 (3) | 0.38615 (13) | 0.0451 (5) | |
S1 | 0.74194 (6) | 0.31020 (11) | 0.81472 (5) | 0.0535 (3) | |
C1 | 0.65892 (18) | 0.3483 (3) | 0.86103 (15) | 0.0345 (5) | |
C2 | 0.51320 (19) | 0.4188 (3) | 0.87965 (15) | 0.0342 (5) | |
C3 | 0.9754 (2) | 0.6751 (4) | 0.84854 (17) | 0.0480 (6) | |
H3 | 0.9595 | 0.6770 | 0.8967 | 0.058* | |
C4 | 0.8821 (2) | 0.6721 (4) | 0.75504 (16) | 0.0438 (6) | |
H4 | 0.8058 | 0.6755 | 0.7414 | 0.053* | |
C5 | 0.90223 (18) | 0.6640 (3) | 0.68118 (15) | 0.0310 (5) | |
C6 | 1.01851 (19) | 0.6645 (4) | 0.70791 (16) | 0.0417 (6) | |
H6 | 1.0375 | 0.6606 | 0.6616 | 0.050* | |
C7 | 1.1056 (2) | 0.6709 (4) | 0.80326 (17) | 0.0460 (6) | |
H7 | 1.1828 | 0.6721 | 0.8191 | 0.055* | |
C8 | 0.7294 (2) | 0.6805 (4) | 0.41216 (18) | 0.0546 (7) | |
H8 | 0.7437 | 0.7076 | 0.3643 | 0.065* | |
C9 | 0.8213 (2) | 0.6949 (4) | 0.50561 (17) | 0.0509 (7) | |
H9 | 0.8948 | 0.7324 | 0.5193 | 0.061* | |
C10 | 0.80481 (18) | 0.6537 (3) | 0.57918 (15) | 0.0328 (5) | |
C11 | 0.6921 (2) | 0.6022 (4) | 0.55197 (16) | 0.0444 (6) | |
H11 | 0.6752 | 0.5737 | 0.5982 | 0.053* | |
C12 | 0.6055 (2) | 0.5932 (4) | 0.45693 (17) | 0.0495 (6) | |
H12 | 0.5306 | 0.5589 | 0.4410 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0317 (10) | 0.0518 (12) | 0.0198 (9) | −0.0015 (8) | 0.0114 (8) | −0.0012 (8) |
N2 | 0.0271 (10) | 0.0541 (12) | 0.0266 (10) | 0.0016 (8) | 0.0109 (8) | −0.0015 (8) |
N3 | 0.0343 (10) | 0.0523 (12) | 0.0273 (10) | 0.0052 (9) | 0.0170 (9) | 0.0023 (9) |
N4 | 0.0319 (11) | 0.0795 (16) | 0.0330 (11) | 0.0092 (10) | 0.0162 (9) | 0.0050 (10) |
N5 | 0.0352 (11) | 0.0506 (13) | 0.0296 (10) | −0.0007 (9) | 0.0102 (9) | 0.0000 (9) |
N6 | 0.0417 (12) | 0.0526 (13) | 0.0265 (10) | 0.0024 (9) | 0.0086 (9) | −0.0008 (9) |
S1 | 0.0467 (4) | 0.0750 (5) | 0.0509 (4) | −0.0104 (3) | 0.0342 (4) | −0.0130 (3) |
C1 | 0.0324 (12) | 0.0398 (13) | 0.0284 (12) | −0.0063 (10) | 0.0145 (10) | −0.0040 (9) |
C2 | 0.0344 (12) | 0.0412 (13) | 0.0264 (12) | −0.0010 (10) | 0.0157 (10) | 0.0019 (10) |
C3 | 0.0418 (14) | 0.0716 (18) | 0.0290 (13) | −0.0008 (12) | 0.0178 (11) | −0.0008 (12) |
C4 | 0.0313 (12) | 0.0660 (17) | 0.0316 (13) | −0.0017 (11) | 0.0152 (11) | 0.0021 (11) |
C5 | 0.0308 (11) | 0.0312 (12) | 0.0268 (11) | −0.0009 (9) | 0.0125 (9) | 0.0011 (9) |
C6 | 0.0348 (13) | 0.0588 (16) | 0.0328 (13) | −0.0009 (11) | 0.0190 (11) | −0.0007 (11) |
C7 | 0.0275 (12) | 0.0640 (17) | 0.0391 (14) | −0.0004 (11) | 0.0129 (11) | 0.0008 (12) |
C8 | 0.0579 (17) | 0.0742 (19) | 0.0285 (13) | −0.0081 (14) | 0.0211 (13) | 0.0033 (12) |
C9 | 0.0401 (14) | 0.0761 (19) | 0.0322 (13) | −0.0137 (13) | 0.0165 (12) | 0.0004 (12) |
C10 | 0.0333 (12) | 0.0336 (12) | 0.0266 (11) | 0.0004 (9) | 0.0128 (10) | −0.0005 (9) |
C11 | 0.0353 (13) | 0.0659 (17) | 0.0298 (12) | −0.0015 (11) | 0.0160 (11) | −0.0011 (11) |
C12 | 0.0324 (13) | 0.0705 (18) | 0.0352 (14) | −0.0017 (12) | 0.0113 (11) | −0.0038 (12) |
N1—C1 | 1.362 (3) | C3—H3 | 0.9300 |
N1—C2 | 1.365 (3) | C4—C5 | 1.388 (3) |
N1—H1 | 0.8600 | C4—H4 | 0.9300 |
N2—C1 | 1.322 (3) | C5—C6 | 1.386 (3) |
N2—N3 | 1.390 (2) | C5—C10 | 1.486 (3) |
N2—H2 | 0.8600 | C6—C7 | 1.374 (3) |
N3—C2 | 1.304 (3) | C6—H6 | 0.9300 |
N4—C2 | 1.365 (3) | C7—H7 | 0.9300 |
N4—H4A | 0.8600 | C8—C9 | 1.374 (3) |
N4—H4B | 0.8600 | C8—H8 | 0.9300 |
N5—C7 | 1.323 (3) | C9—C10 | 1.380 (3) |
N5—C3 | 1.331 (3) | C9—H9 | 0.9300 |
N6—C8 | 1.324 (3) | C10—C11 | 1.384 (3) |
N6—C12 | 1.328 (3) | C11—C12 | 1.370 (3) |
S1—C1 | 1.685 (2) | C11—H11 | 0.9300 |
C3—C4 | 1.376 (3) | C12—H12 | 0.9300 |
C1—N1—C2 | 107.97 (17) | C6—C5—C4 | 116.2 (2) |
C1—N1—H1 | 126.0 | C6—C5—C10 | 121.74 (19) |
C2—N1—H1 | 126.0 | C4—C5—C10 | 122.03 (19) |
C1—N2—N3 | 113.61 (18) | C7—C6—C5 | 119.6 (2) |
C1—N2—H2 | 123.2 | C7—C6—H6 | 120.2 |
N3—N2—H2 | 123.2 | C5—C6—H6 | 120.2 |
C2—N3—N2 | 102.64 (17) | N5—C7—C6 | 124.5 (2) |
C2—N4—H4A | 120.0 | N5—C7—H7 | 117.8 |
C2—N4—H4B | 120.0 | C6—C7—H7 | 117.8 |
H4A—N4—H4B | 120.0 | N6—C8—C9 | 123.9 (2) |
C7—N5—C3 | 116.07 (19) | N6—C8—H8 | 118.0 |
C8—N6—C12 | 115.9 (2) | C9—C8—H8 | 118.0 |
N2—C1—N1 | 104.02 (18) | C8—C9—C10 | 120.2 (2) |
N2—C1—S1 | 127.97 (17) | C8—C9—H9 | 119.9 |
N1—C1—S1 | 127.98 (16) | C10—C9—H9 | 119.9 |
N3—C2—N1 | 111.74 (18) | C9—C10—C11 | 115.8 (2) |
N3—C2—N4 | 125.82 (19) | C9—C10—C5 | 121.9 (2) |
N1—C2—N4 | 122.42 (19) | C11—C10—C5 | 122.21 (19) |
N5—C3—C4 | 123.8 (2) | C12—C11—C10 | 120.0 (2) |
N5—C3—H3 | 118.1 | C12—C11—H11 | 120.0 |
C4—C3—H3 | 118.1 | C10—C11—H11 | 120.0 |
C3—C4—C5 | 119.8 (2) | N6—C12—C11 | 124.1 (2) |
C3—C4—H4 | 120.1 | N6—C12—H12 | 117.9 |
C5—C4—H4 | 120.1 | C11—C12—H12 | 117.9 |
C1—N2—N3—C2 | 1.2 (3) | C3—N5—C7—C6 | −0.6 (4) |
N3—N2—C1—N1 | −1.6 (2) | C5—C6—C7—N5 | 0.5 (4) |
N3—N2—C1—S1 | 176.54 (17) | C12—N6—C8—C9 | 0.1 (4) |
C2—N1—C1—N2 | 1.4 (2) | N6—C8—C9—C10 | 0.8 (4) |
C2—N1—C1—S1 | −176.79 (18) | C8—C9—C10—C11 | −1.0 (4) |
N2—N3—C2—N1 | −0.3 (2) | C8—C9—C10—C5 | 178.9 (2) |
N2—N3—C2—N4 | 178.2 (2) | C6—C5—C10—C9 | −17.5 (3) |
C1—N1—C2—N3 | −0.7 (3) | C4—C5—C10—C9 | 163.0 (2) |
C1—N1—C2—N4 | −179.3 (2) | C6—C5—C10—C11 | 162.4 (2) |
C7—N5—C3—C4 | −0.6 (4) | C4—C5—C10—C11 | −17.1 (3) |
N5—C3—C4—C5 | 1.7 (4) | C9—C10—C11—C12 | 0.5 (4) |
C3—C4—C5—C6 | −1.6 (3) | C5—C10—C11—C12 | −179.4 (2) |
C3—C4—C5—C10 | 177.8 (2) | C8—N6—C12—C11 | −0.7 (4) |
C4—C5—C6—C7 | 0.6 (3) | C10—C11—C12—N6 | 0.4 (4) |
C10—C5—C6—C7 | −178.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N6i | 0.86 | 1.98 | 2.828 (3) | 171 |
N2—H2···N5ii | 0.86 | 2.00 | 2.829 (3) | 163 |
N4—H4A···N3iii | 0.86 | 2.33 | 3.151 (3) | 159 |
N4—H4B···S1iv | 0.86 | 2.82 | 3.424 (2) | 129 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C10H8N2·C2H4N4S |
Mr | 272.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.5151 (12), 6.9680 (5), 16.5529 (14) |
β (°) | 122.385 (2) |
V (Å3) | 1316.39 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.40 × 0.30 × 0.21 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.910, 0.951 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6507, 2315, 1725 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.114, 1.09 |
No. of reflections | 2315 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.29 |
Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N6i | 0.86 | 1.98 | 2.828 (3) | 171 |
N2—H2···N5ii | 0.86 | 2.00 | 2.829 (3) | 163 |
N4—H4A···N3iii | 0.86 | 2.33 | 3.151 (3) | 159 |
N4—H4B···S1iv | 0.86 | 2.82 | 3.424 (2) | 129 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (No.21171119), the National High Technology Research and Development Program 863 of China (2012 A A063201), the Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program) under grant Nos. 2007CB310408 and 2006CB302901, and the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020.
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Supramolecular compounds have received much attention due to their structural diversities and potential applications as new materials. The ligand 3-amino-1,2,4-triazole-5-thione(3-AMT), with one –SH, one –NH2 group and three potential coordination nitrogen atoms of triazole, is excellent in building metal-organic supramolecular structures (Hao et al., 2010; Ma et al., 2008; Rakova et al., 2003). Moreover, its nitrogen atom and sulfur atom may be involved in hydrogen bonding (Deng et al., 2005; Downie et al., 1972).
The title compound was unexpectedly obtained in the course of synthesizing 3-AMT-Zn(II) complexes. The molecular structure of the title compound is shown in Fig.1. The crystal structure of C2H2N4S.C10H8N2 has been determined at room temperature. The compound has the space group P2(1)/c, with a = 13.5151 (12), b = 6.9680 (5), c = 16.5529 (14) Å and beta = 122.385 (2)°. The hydrogen bonds are formed between the N—H donors of 3-AMT and the nitrogen atoms from 4,4'-bipyridine and 3-AMT, and the atoms N6, N5 and N3 act as acceptors with d(N1···O6) = 2.828 (3) Å, d(N2···N5) = 2.829 (3) Å, d(N4···N3) = 3.151 (3) Å, N1—H1···N6 =171°, N2—H2···N5 =163° and N4—H4A···N3 =159°, which are just similar to the corresponding distances and angles in the compound of C10H8N2.2C2H3N3S2 (Deng et al., 2005). Intermolecular hydrogen bonds N—H···N and N—H···S between the components lead to the formation of a three-dimensional network (Fig.2). Furthermore, the structure is stabilized by the face to face π-π stacking interactions between 4,4'-bipyridine and triazole ring, with the centroid-centroid distance of 2.976 (2) Å.