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access2-(4H-1,2,4-Triazol-4-yl)pyrimidine
aTianjin Key Laboratory of Structure and Performances for Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China
*Correspondence e-mail: wangying790601@163.com
The title compound, C6H5N5, is almost planar, the triazole and pyrimidine rings forming a dihedral angle of 2.9 (13)°.
Related literature
For the synthesis of the title compound, see: Wiley & Hart (1953![[Wiley, R. H. & Hart, A. J. (1953). J. Org. Chem. 18, 1368-1371.]](../../../../../../logos/arrows/e_arr.gif "Wiley, R. H. & Hart, A. J. (1953). J. Org. Chem. 18, 1368-1371.")
). For properties of related compounds, see: Haasnoot (2000).
![[Scheme 1]](aa2030scheme1.gif)
Experimental
Crystal data
|
![[P \overline 1]](teximages/aa2030fi1.gif)
Data collection: SMART (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
contains datablocks I, gllobal. DOI: 10.1107/S1600536811051968/aa2030sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536811051968/aa2030Isup2.hkl
A mixture of 1.2 g (0.012 mol) of pyrimidin-2-amine and 2.0 g (0.011 mol) of diformylhydrazine was heated slowly to 160–170 °C for 30 min. The crystals, which separated on cooling, were collected and recrystallized from water and acetonitrile and dried on air. Yield 0.7 g (43%). Anal. Calc. for C6H5N5 (%): C, 50.52; H, 5.30; N 44.18. Found (%): C, 50.59; H, 5.36; N 44.23.
Hydrogen atoms were included into calculated positions and refined as riding on the C atoms with C—H = 0.93 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). Friedel pairs were averaged for the data used on the final cycles of the refinement.
Data collection: SMART (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./aa2030fig1thm.gif) | Fig. 1. An ORTEP-3 view of the title compound with the displacement ellipsoids shown on 30% probability level. |
| C6H5N5 | Z = 2 |
| Mr = 147.15 | F(000) = 152 |
| Triclinic, P1 | Dx = 1.490 Mg m−3 Dm = 1.490 Mg m−3 Dm measured by not measured |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.6929 (10) Å | Cell parameters from 786 reflections |
| b = 7.7355 (14) Å | θ = 2.6–25.9° |
| c = 8.6102 (15) Å | µ = 0.10 mm−1 |
| α = 67.233 (2)° | T = 293 K |
| β = 80.755 (2)° | Sheet, colourless |
| γ = 69.837 (2)° | 0.46 × 0.34 × 0.12 mm |
| V = 328.04 (10) Å3 |
| Bruker SMART CCD area-detector diffractometer | 1154 independent reflections |
| Radiation source: fine-focus sealed tube | 916 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.010 |
| phi and ω scans | θmax = 25.0°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
| Tmin = 0.954, Tmax = 0.988 | k = −9→6 |
| 1803 measured reflections | l = −10→10 |
| 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.101 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0595P)2 + 0.0336P] where P = (Fo2 + 2Fc2)/3 |
| 1154 reflections | (Δ/σ)max < 0.001 |
| 100 parameters | Δρmax = 0.11 e Å−3 |
| 0 restraints | Δρmin = −0.17 e Å−3 |
| C6H5N5 | γ = 69.837 (2)° |
| Mr = 147.15 | V = 328.04 (10) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 5.6929 (10) Å | Mo Kα radiation |
| b = 7.7355 (14) Å | µ = 0.10 mm−1 |
| c = 8.6102 (15) Å | T = 293 K |
| α = 67.233 (2)° | 0.46 × 0.34 × 0.12 mm |
| β = 80.755 (2)° |
| Bruker SMART CCD area-detector diffractometer | 1154 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 916 reflections with I > 2σ(I) |
| Tmin = 0.954, Tmax = 0.988 | Rint = 0.010 |
| 1803 measured reflections |
| R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
| wR(F2) = 0.101 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.11 e Å−3 |
| 1154 reflections | Δρmin = −0.17 e Å−3 |
| 100 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | 0.5226 (2) | 0.81660 (19) | 0.85375 (15) | 0.0447 (4) | |
| N2 | 0.2458 (2) | 0.66148 (18) | 0.82287 (15) | 0.0450 (4) | |
| N3 | 0.20693 (19) | 0.75348 (16) | 1.05328 (14) | 0.0371 (3) | |
| N4 | 0.0968 (3) | 0.8138 (2) | 1.28772 (16) | 0.0564 (4) | |
| N5 | −0.0695 (2) | 0.7314 (2) | 1.26282 (16) | 0.0543 (4) | |
| C1 | 0.3340 (2) | 0.74312 (19) | 0.89977 (17) | 0.0349 (3) | |
| C2 | 0.3638 (3) | 0.6558 (2) | 0.6765 (2) | 0.0526 (4) | |
| H2 | 0.3095 | 0.6009 | 0.6157 | 0.063* | |
| C3 | 0.5620 (3) | 0.7281 (2) | 0.61289 (19) | 0.0525 (4) | |
| H3 | 0.6422 | 0.7236 | 0.5109 | 0.063* | |
| C4 | 0.6357 (3) | 0.8070 (2) | 0.7069 (2) | 0.0511 (4) | |
| H4 | 0.7702 | 0.8562 | 0.6671 | 0.061* | |
| C5 | 0.2575 (3) | 0.8247 (2) | 1.16196 (19) | 0.0483 (4) | |
| H5 | 0.3898 | 0.8746 | 1.1478 | 0.058* | |
| C6 | 0.0005 (3) | 0.6975 (2) | 1.12413 (19) | 0.0464 (4) | |
| H6 | −0.0795 | 0.6422 | 1.0787 | 0.056* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0397 (6) | 0.0550 (8) | 0.0439 (7) | −0.0210 (6) | 0.0051 (5) | −0.0192 (6) |
| N2 | 0.0507 (7) | 0.0556 (8) | 0.0394 (7) | −0.0242 (6) | 0.0061 (5) | −0.0245 (6) |
| N3 | 0.0385 (6) | 0.0415 (7) | 0.0347 (7) | −0.0148 (5) | 0.0037 (5) | −0.0172 (5) |
| N4 | 0.0665 (9) | 0.0667 (9) | 0.0457 (8) | −0.0241 (7) | 0.0086 (6) | −0.0314 (7) |
| N5 | 0.0534 (8) | 0.0674 (10) | 0.0471 (8) | −0.0232 (7) | 0.0136 (6) | −0.0278 (7) |
| C1 | 0.0347 (7) | 0.0347 (8) | 0.0336 (7) | −0.0089 (6) | 0.0000 (5) | −0.0126 (6) |
| C2 | 0.0641 (10) | 0.0598 (10) | 0.0415 (9) | −0.0213 (8) | 0.0045 (7) | −0.0266 (8) |
| C3 | 0.0561 (10) | 0.0581 (10) | 0.0371 (9) | −0.0134 (8) | 0.0107 (7) | −0.0190 (8) |
| C4 | 0.0415 (8) | 0.0609 (10) | 0.0456 (9) | −0.0190 (8) | 0.0097 (7) | −0.0151 (8) |
| C5 | 0.0556 (9) | 0.0580 (10) | 0.0448 (9) | −0.0256 (8) | 0.0040 (7) | −0.0278 (8) |
| C6 | 0.0430 (8) | 0.0593 (10) | 0.0449 (9) | −0.0233 (7) | 0.0090 (6) | −0.0245 (7) |
| N1—C1 | 1.3199 (18) | N5—C6 | 1.2927 (19) |
| N1—C4 | 1.3407 (19) | C2—C3 | 1.373 (2) |
| N2—C1 | 1.3185 (18) | C2—H2 | 0.9300 |
| N2—C2 | 1.3386 (18) | C3—C4 | 1.368 (2) |
| N3—C6 | 1.3624 (18) | C3—H3 | 0.9300 |
| N3—C5 | 1.3629 (18) | C4—H4 | 0.9300 |
| N3—C1 | 1.4184 (17) | C5—H5 | 0.9300 |
| N4—C5 | 1.2965 (19) | C6—H6 | 0.9300 |
| N4—N5 | 1.3915 (19) | ||
| C1—N1—C4 | 114.10 (13) | C4—C3—C2 | 116.74 (14) |
| C1—N2—C2 | 114.64 (13) | C4—C3—H3 | 121.6 |
| C6—N3—C5 | 103.94 (12) | C2—C3—H3 | 121.6 |
| C6—N3—C1 | 127.43 (12) | N1—C4—C3 | 122.95 (14) |
| C5—N3—C1 | 128.61 (12) | N1—C4—H4 | 118.5 |
| C5—N4—N5 | 106.86 (12) | C3—C4—H4 | 118.5 |
| C6—N5—N4 | 107.05 (12) | N4—C5—N3 | 111.03 (13) |
| N2—C1—N1 | 129.15 (13) | N4—C5—H5 | 124.5 |
| N2—C1—N3 | 115.06 (12) | N3—C5—H5 | 124.5 |
| N1—C1—N3 | 115.79 (12) | N5—C6—N3 | 111.12 (13) |
| N2—C2—C3 | 122.41 (14) | N5—C6—H6 | 124.4 |
| N2—C2—H2 | 118.8 | N3—C6—H6 | 124.4 |
| C3—C2—H2 | 118.8 | ||
| C5—N4—N5—C6 | 0.04 (17) | N2—C2—C3—C4 | 0.2 (2) |
| C2—N2—C1—N1 | −1.0 (2) | C1—N1—C4—C3 | 0.0 (2) |
| C2—N2—C1—N3 | 178.77 (12) | C2—C3—C4—N1 | −0.4 (2) |
| C4—N1—C1—N2 | 0.8 (2) | N5—N4—C5—N3 | 0.04 (18) |
| C4—N1—C1—N3 | −179.02 (12) | C6—N3—C5—N4 | −0.10 (17) |
| C6—N3—C1—N2 | −3.3 (2) | C1—N3—C5—N4 | 178.59 (13) |
| C5—N3—C1—N2 | 178.33 (13) | N4—N5—C6—N3 | −0.11 (17) |
| C6—N3—C1—N1 | 176.55 (13) | C5—N3—C6—N5 | 0.13 (17) |
| C5—N3—C1—N1 | −1.8 (2) | C1—N3—C6—N5 | −178.59 (13) |
| C1—N2—C2—C3 | 0.5 (2) |
Experimental details
| Crystal data | |
| Chemical formula | C6H5N5 |
| Mr | 147.15 |
| Crystal system, space group | Triclinic, P1 |
| Temperature (K) | 293 |
| a, b, c (Å) | 5.6929 (10), 7.7355 (14), 8.6102 (15) |
| α, β, γ (°) | 67.233 (2), 80.755 (2), 69.837 (2) |
| V (Å3) | 328.04 (10) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.10 |
| Crystal size (mm) | 0.46 × 0.34 × 0.12 |
| Data collection | |
| Diffractometer | Bruker SMART CCD area-detector diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
| Tmin, Tmax | 0.954, 0.988 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 1803, 1154, 916 |
| Rint | 0.010 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.101, 1.03 |
| No. of reflections | 1154 |
| No. of parameters | 100 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.11, −0.17 |
Computer programs: SMART (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported financially by Tianjin Normal University (grant No. 5RL090), the Natural Science Foundation of Tianjin (grant No. 11JCYBJC03600) and the Young Scientist Fund (grant No. 52 G10005).
References
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Haasnoot, J. G. (2000). Coord. Chem. Rev. 200–2002, 131–185. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wiley, R. H. & Hart, A. J. (1953). J. Org. Chem. 18, 1368–1371. CrossRef CAS Web of Science Google Scholar
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Many molecular compounds exhibit interesting magnetic and luminescent properties (Haasnoot, 2000). One of the requirements for posessing such macroscopic properties is to create interactions between the molecular units and the active sites within the crystal lattices. 1,2,4-Triazole and its derivatives are interesting bridging ligands. In the title compound the triazole and the pyrimidine rings are almost in the same plane, the dihedral angles between them is 2.9 (13)°.