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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o427.
Published online 2010 January 23. doi:  10.1107/S1600536810002187
PMCID: PMC2979911

5,6-Diphenyl-3-(3-pyrid­yl)-1,2,4-triazine

Abstract

In the mol­ecule of the title compound, C20H14N4, the triazine ring is attached to two phenyl rings and one pyridine ring. In the crystal, mol­ecules are linked by inter­molecular C—H(...)N hydrogen bonds. The crystal packing is also stabilized by C—H(...)π inter­actions.

Related literature

For applications of substituted 1,2,4-triazines, see: Denecke et al. (2005 [triangle]); Maheshwari et al. (2006 [triangle]): Zhao et al. (2003 [triangle]).

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Object name is e-66-0o427-scheme1.jpg

Experimental

Crystal data

  • C20H14N4
  • M r = 310.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o427-efi1.jpg
  • a = 14.4775 (16) Å
  • b = 7.0923 (8) Å
  • c = 18.5786 (15) Å
  • β = 125.587 (6)°
  • V = 1551.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.31 × 0.28 × 0.26 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • 9802 measured reflections
  • 3770 independent reflections
  • 2184 reflections with I > 2σ(I)
  • R int = 0.033
  • 3 standard reflections every 200 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.125
  • S = 1.04
  • 3770 reflections
  • 218 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL/PC (Sheldrick, 2008 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002187/hg2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002187/hg2609Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported financially by the Fund of Doctors of Shandaong Province (No. 2007BS04046).

supplementary crystallographic information

Comment

The increasing interest in the chemistry of substituted 1,2,4-triazine is due to their various applications: commercial dyes, herbicides (Zhao et al., 2003), antiviral, antitumor drug (Maheshwari et al., 2006) and selective extracting agents in the separation of lanthanides and actinides in the management of nuclear wastes (Denecke et al., 2005). The title compound belongs to the family of these compounds. We have synthesized the title compound and describe its structure here.

In the title compound, the bond lengths and angles are generally normal. The dihedral angles between triazine ring(p1) with the pyridine ring (p2), C1—C6 (p3) and C9—C14 (p4) phenyl rings are 2.94 (2)°, 53.35 (2)° and 50.43 (2)°, respectively. There exist intermolecular C—H···N hydrogen bond and C—H···π supramolecular interactions in the crystal lattice. The donor and acceptor distance is 2.8235Å for C20—H20A···N3. In addition, there are obvious intermolecular C—H···π interactions between C13—H13A and pyridine ring (Cg(2)), C19—H19A and C1—C6 phenyl ring (Cg(3)). In the solid state, all above intermolecular interactions in the title compound stabilize the crystal packing structure.

Experimental

To a mixture of (3-pyridylcarbonyl)hydrazine (0.828 g, 6 mmol) and benzil (1.26 g, 6 mmol) was added ammonium acetate (4.62 g, 0.06 mol) and 1 ml of acetic acid. The mixture was heated by conventional microwave oven for 5 min at 453 K. Upon rapid cooling of the reaction vessel to 313 K, a yellow precipitate formed, which was washed with water to afford the title compound (yield 45.3%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature for three days.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93–0.96 Å, respectively, and with Uiso(H) = 1.2Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C20H14N4F(000) = 648
Mr = 310.35Dx = 1.329 Mg m3
Monoclinic, P21/cMelting point: 444 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.4775 (16) ÅCell parameters from 25 reflections
b = 7.0923 (8) Åθ = 1.7–28.3°
c = 18.5786 (15) ŵ = 0.08 mm1
β = 125.587 (6)°T = 293 K
V = 1551.3 (3) Å3Block, yellow
Z = 40.31 × 0.28 × 0.26 mm

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.033
Radiation source: fine-focus sealed tubeθmax = 28.3°, θmin = 1.7°
graphiteh = −16→19
ω scansk = −7→9
9802 measured reflectionsl = −24→20
3770 independent reflections3 standard reflections every 200 reflections
2184 reflections with I > 2σ(I) intensity decay: none

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.125w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3770 reflectionsΔρmax = 0.16 e Å3
218 parametersΔρmin = −0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0105 (17)

Special details

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)

xyzUiso*/Ueq
N10.40833 (10)0.74465 (17)0.84881 (7)0.0422 (3)
N20.48148 (11)0.5785 (2)0.75648 (8)0.0554 (4)
N30.55312 (11)0.5984 (2)0.84483 (8)0.0546 (4)
C200.69841 (13)0.6021 (2)1.03161 (9)0.0505 (4)
H20A0.72150.54560.99930.061*
C10.19450 (14)0.9625 (2)0.65096 (9)0.0512 (4)
H1B0.24150.98970.63340.061*
C20.09076 (15)1.0535 (2)0.61123 (10)0.0598 (5)
H2B0.06881.14310.56740.072*
C30.02025 (14)1.0123 (3)0.63613 (10)0.0608 (5)
H3B−0.04961.07270.60870.073*
C40.05291 (13)0.8823 (2)0.70138 (10)0.0555 (4)
H4B0.00500.85410.71800.067*
C50.15676 (12)0.7931 (2)0.74260 (9)0.0475 (4)
H5A0.17930.70730.78790.057*
C60.22752 (12)0.8308 (2)0.71683 (9)0.0410 (4)
C70.33957 (11)0.7350 (2)0.76126 (8)0.0398 (4)
C80.37453 (12)0.6390 (2)0.71427 (9)0.0430 (4)
C90.29850 (13)0.5980 (2)0.61817 (9)0.0437 (4)
C100.19430 (15)0.5132 (3)0.58174 (10)0.0625 (5)
H10A0.17100.48330.61760.075*
C110.12424 (16)0.4725 (3)0.49224 (11)0.0692 (5)
H11A0.05460.41410.46840.083*
C120.15742 (15)0.5181 (2)0.43853 (10)0.0581 (5)
H12A0.11020.49120.37830.070*
C130.25980 (15)0.6030 (2)0.47375 (10)0.0578 (5)
H13A0.28190.63540.43730.069*
C140.33114 (14)0.6412 (2)0.56364 (10)0.0531 (4)
H14A0.40160.69640.58740.064*
C150.51278 (12)0.6718 (2)0.88740 (9)0.0410 (4)
C160.59002 (12)0.6778 (2)0.98515 (9)0.0400 (4)
C170.55691 (13)0.7604 (2)1.03439 (9)0.0506 (4)
H17A0.48450.81121.00620.061*
C180.63165 (14)0.7668 (2)1.12525 (10)0.0569 (5)
H18A0.61110.82311.15920.068*
C190.73715 (14)0.6882 (2)1.16431 (10)0.0575 (5)
H19A0.78760.69321.22570.069*
N40.77171 (11)0.6048 (2)1.11941 (8)0.0585 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0368 (7)0.0495 (8)0.0368 (6)0.0013 (6)0.0193 (5)−0.0009 (6)
N20.0498 (9)0.0713 (10)0.0462 (8)0.0062 (7)0.0285 (7)−0.0046 (7)
N30.0434 (8)0.0729 (10)0.0452 (8)0.0091 (7)0.0244 (7)−0.0038 (7)
C200.0439 (9)0.0556 (10)0.0456 (9)0.0041 (7)0.0223 (8)0.0010 (8)
C10.0526 (10)0.0574 (10)0.0405 (8)−0.0012 (8)0.0254 (7)0.0024 (8)
C20.0567 (11)0.0541 (11)0.0424 (9)0.0059 (8)0.0138 (8)0.0065 (8)
C30.0386 (9)0.0666 (12)0.0519 (10)0.0081 (8)0.0119 (8)−0.0059 (9)
C40.0402 (9)0.0705 (12)0.0524 (10)−0.0002 (8)0.0249 (8)−0.0068 (9)
C50.0436 (9)0.0577 (10)0.0378 (8)0.0035 (7)0.0217 (7)0.0029 (7)
C60.0372 (8)0.0486 (9)0.0319 (7)−0.0006 (7)0.0171 (6)−0.0040 (6)
C70.0375 (8)0.0436 (9)0.0371 (8)−0.0029 (6)0.0210 (7)−0.0006 (6)
C80.0421 (8)0.0484 (9)0.0400 (8)−0.0013 (7)0.0248 (7)−0.0011 (7)
C90.0477 (9)0.0442 (9)0.0414 (8)0.0003 (7)0.0271 (7)−0.0027 (7)
C100.0674 (12)0.0758 (13)0.0490 (10)−0.0227 (10)0.0366 (9)−0.0126 (9)
C110.0671 (12)0.0810 (14)0.0546 (11)−0.0240 (10)0.0326 (10)−0.0166 (9)
C120.0664 (12)0.0608 (11)0.0397 (9)0.0004 (9)0.0267 (8)−0.0065 (8)
C130.0681 (12)0.0670 (12)0.0479 (10)0.0031 (9)0.0392 (9)0.0005 (8)
C140.0526 (10)0.0626 (11)0.0492 (9)−0.0026 (8)0.0325 (8)−0.0038 (8)
C150.0363 (8)0.0439 (9)0.0407 (8)0.0005 (7)0.0211 (7)−0.0006 (7)
C160.0349 (8)0.0403 (8)0.0420 (8)−0.0022 (6)0.0206 (7)−0.0005 (7)
C170.0409 (9)0.0596 (10)0.0455 (9)0.0058 (7)0.0220 (7)0.0009 (8)
C180.0576 (11)0.0638 (11)0.0452 (9)0.0006 (9)0.0276 (8)−0.0052 (8)
C190.0502 (10)0.0636 (11)0.0412 (9)−0.0057 (8)0.0167 (8)0.0005 (8)
N40.0426 (8)0.0701 (10)0.0471 (8)0.0048 (7)0.0173 (7)0.0048 (7)

Geometric parameters (Å, °)

N1—C71.3253 (16)C8—C91.4823 (19)
N1—C151.3440 (18)C9—C141.379 (2)
N2—C81.3356 (19)C9—C101.381 (2)
N2—N31.3448 (17)C10—C111.383 (2)
N3—C151.3322 (18)C10—H10A0.9300
C20—N41.3313 (18)C11—C121.375 (2)
C20—C161.385 (2)C11—H11A0.9300
C20—H20A0.9300C12—C131.363 (2)
C1—C61.385 (2)C12—H12A0.9300
C1—C21.388 (2)C13—C141.386 (2)
C1—H1B0.9300C13—H13A0.9300
C2—C31.375 (2)C14—H14A0.9300
C2—H2B0.9300C15—C161.4788 (19)
C3—C41.370 (2)C16—C171.386 (2)
C3—H3B0.9300C17—C181.377 (2)
C4—C51.381 (2)C17—H17A0.9300
C4—H4B0.9300C18—C191.371 (2)
C5—C61.386 (2)C18—H18A0.9300
C5—H5A0.9300C19—N41.335 (2)
C6—C71.4887 (19)C19—H19A0.9300
C7—C81.4126 (19)
C7—N1—C15116.31 (12)C10—C9—C8120.64 (13)
C8—N2—N3119.33 (12)C9—C10—C11120.51 (15)
C15—N3—N2118.20 (13)C9—C10—H10A119.7
N4—C20—C16124.33 (15)C11—C10—H10A119.7
N4—C20—H20A117.8C12—C11—C10120.12 (17)
C16—C20—H20A117.8C12—C11—H11A119.9
C6—C1—C2119.60 (16)C10—C11—H11A119.9
C6—C1—H1B120.2C13—C12—C11119.82 (15)
C2—C1—H1B120.2C13—C12—H12A120.1
C3—C2—C1120.50 (16)C11—C12—H12A120.1
C3—C2—H2B119.8C12—C13—C14120.27 (15)
C1—C2—H2B119.8C12—C13—H13A119.9
C4—C3—C2119.95 (16)C14—C13—H13A119.9
C4—C3—H3B120.0C9—C14—C13120.54 (16)
C2—C3—H3B120.0C9—C14—H14A119.7
C3—C4—C5120.19 (16)C13—C14—H14A119.7
C3—C4—H4B119.9N3—C15—N1125.41 (13)
C5—C4—H4B119.9N3—C15—C16117.45 (13)
C4—C5—C6120.33 (15)N1—C15—C16117.13 (12)
C4—C5—H5A119.8C20—C16—C17117.00 (13)
C6—C5—H5A119.8C20—C16—C15121.79 (13)
C1—C6—C5119.42 (14)C17—C16—C15121.21 (13)
C1—C6—C7120.15 (13)C18—C17—C16119.76 (15)
C5—C6—C7120.41 (13)C18—C17—H17A120.1
N1—C7—C8120.00 (13)C16—C17—H17A120.1
N1—C7—C6117.05 (12)C19—C18—C17118.28 (15)
C8—C7—C6122.95 (12)C19—C18—H18A120.9
N2—C8—C7120.14 (13)C17—C18—H18A120.9
N2—C8—C9116.00 (13)N4—C19—C18123.81 (15)
C7—C8—C9123.86 (13)N4—C19—H19A118.1
C14—C9—C10118.71 (14)C18—C19—H19A118.1
C14—C9—C8120.64 (14)C20—N4—C19116.80 (14)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N4,C16–C20 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C20—H20A···N30.932.492.824 (4)102
C13—H13A···Cg1i0.933.493.345 (4)91
C19—H19A···Cg2ii0.933.673.109 (4)121

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2609).

References

  • Denecke, M. A., Rossberg, A., Panak, P. J., Weigl, M., Schimmelpfennig, B. & Geist, A. (2005). Inorg. Chem.44, 8418–8425. [PubMed]
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst.22, 384–387.
  • Maheshwari, V., Bhattacharyya, D., Fronczek, F. R., Marzilli, P. A. & Marzilli, L. G. (2006). Inorg. Chem.45, 7182–7190. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhao, Z. J., Leister, W. H., Strauss, K. A., Wisnoski, D. D. & Lindsley, C. W. (2003). Tetrahedron Lett.44, 1123–1127.

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