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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3214.
Published online 2009 November 25. doi:  10.1107/S1600536809049174
PMCID: PMC2971754

4-(3-Methyl­phen­yl)-3-phenyl-5-(2-pyrid­yl)-4H-1,2,4-triazole

Abstract

In the title compound, C20H16N4, the m-tolyl and phenyl substituents form dihedral angles of 74.20 (6) and 36.94 (8)°, respectively, with the 1,2,4-triazole ring and the dihedral angle between the triazole and pyridine rings is 36.06 (9)°. In the crystal, mol­ecules are linked by C—H(...)N and C—H(...)π inter­actions.

Related literature

For the synthesis of the title compound, see: Klingsberg (1958 [triangle]). For related structures, see: Wang et al. (2005 [triangle]); Huang et al. (2008 [triangle]).

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Object name is e-65-o3214-scheme1.jpg

Experimental

Crystal data

  • C20H16N4
  • M r = 312.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3214-efi1.jpg
  • a = 11.246 (3) Å
  • b = 9.377 (2) Å
  • c = 18.956 (5) Å
  • β = 124.655 (16)°
  • V = 1644.3 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.65 × 0.50 × 0.27 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.787, T max = 1.000
  • 16277 measured reflections
  • 3751 independent reflections
  • 2691 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.162
  • S = 1.06
  • 3751 reflections
  • 218 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049174/gk2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049174/gk2238Isup2.hkl

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

Acknowledgments

We are grateful to Jingye Pharmochemical Pilot Plant for financial assistance through project 8507041056.

supplementary crystallographic information

Comment

Recently we have prepared some new 1,2,4-triazoles and their complexes (Wang et al., 2005; Huang et al., 2008). We report here the crystal structure of the title compound.

Experimental

The title compound was prepared by the reaction of 3,3'– dimethylphenylphosphazoanilide (2.90, 12 mmol) with N-benzoyl-N'-(2-pyridoyl)hydrazine (2.41 g, 10 mmol) in N,N-dimethylaniline at 463–473 K for 5 hrs (Klingsberg, 1958). Single crystals suitable for X-ray diffraction were obtained by recrystallization from water.

Refinement

Positional parameters of all the H atoms were calculated geometrically. The H atoms were allowed to ride on the C atoms to which they were bonded, riding with C—H = 0.93 Å (aromatic) and 0.96 Å (methyl); Uiso(H) = 1.2 or 1.5 times Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound with the atom labelling. Displacement ellipsoids are shown at the 30% probability level.

Crystal data

C20H16N4F(000) = 656
Mr = 312.37Dx = 1.262 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3426 reflections
a = 11.246 (3) Åθ = 2.3–27.5°
b = 9.377 (2) ŵ = 0.08 mm1
c = 18.956 (5) ÅT = 293 K
β = 124.655 (16)°Block, white
V = 1644.3 (7) Å30.65 × 0.50 × 0.27 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer3751 independent reflections
Radiation source: fine-focus sealed tube2691 reflections with I > 2σ(I)
graphiteRint = 0.040
ω scanθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)h = −14→14
Tmin = 0.787, Tmax = 1.000k = −12→12
16277 measured reflectionsl = −24→24

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0823P)2 + 0.1727P] where P = (Fo2 + 2Fc2)/3
3751 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = −0.23 e Å3

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
C10.91724 (18)−0.14398 (19)0.88581 (11)0.0461 (4)
C20.74890 (17)−0.02378 (18)0.77576 (11)0.0447 (4)
C31.05742 (18)−0.1952 (2)0.95950 (11)0.0481 (4)
C41.0759 (2)−0.3404 (2)0.97830 (14)0.0603 (5)
H41.0017−0.40380.94270.072*
C51.2038 (2)−0.3906 (2)1.04945 (15)0.0703 (6)
H51.2151−0.48761.06190.084*
C61.3143 (2)−0.2978 (3)1.10189 (14)0.0684 (6)
H61.4005−0.33171.14980.082*
C71.2969 (2)−0.1545 (2)1.08313 (12)0.0618 (5)
H71.3719−0.09171.11860.074*
C81.16981 (19)−0.1029 (2)1.01265 (11)0.0513 (4)
H81.1594−0.00581.00070.062*
C90.67146 (17)0.07496 (19)0.70258 (10)0.0457 (4)
C100.6617 (2)0.1881 (3)0.59246 (13)0.0687 (6)
H100.70400.21010.56360.082*
C110.5267 (2)0.2440 (2)0.56156 (13)0.0679 (6)
H110.47920.30090.51270.081*
C120.4644 (2)0.2140 (2)0.60434 (13)0.0625 (5)
H120.37400.25070.58520.075*
C130.53747 (18)0.1287 (2)0.67597 (12)0.0529 (5)
H130.49730.10740.70620.063*
C141.00456 (17)0.05403 (19)0.83598 (10)0.0445 (4)
C151.08632 (18)−0.0030 (2)0.80966 (11)0.0510 (4)
H151.0713−0.09670.79030.061*
C161.19103 (19)0.0793 (2)0.81200 (13)0.0595 (5)
C171.2116 (2)0.2171 (3)0.84272 (14)0.0676 (6)
H171.28150.27350.84470.081*
C181.1320 (2)0.2735 (2)0.87042 (13)0.0693 (6)
H181.14940.36600.89170.083*
C191.0255 (2)0.1913 (2)0.86644 (12)0.0583 (5)
H190.96950.22830.88400.070*
C201.2756 (3)0.0194 (3)0.7795 (2)0.1004 (10)
H20A1.26600.08140.73630.151*
H20B1.2390−0.07340.75550.151*
H20C1.37570.01200.82620.151*
N10.68517 (15)−0.12089 (17)0.79297 (10)0.0527 (4)
N20.79217 (16)−0.19790 (17)0.86336 (10)0.0536 (4)
N30.89575 (14)−0.03337 (15)0.83260 (9)0.0441 (3)
N40.73453 (16)0.1044 (2)0.66152 (10)0.0615 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0450 (9)0.0508 (9)0.0478 (9)−0.0015 (8)0.0295 (8)0.0013 (8)
C20.0375 (9)0.0539 (9)0.0450 (9)−0.0015 (7)0.0247 (8)−0.0039 (8)
C30.0455 (9)0.0578 (10)0.0489 (9)0.0031 (8)0.0316 (8)0.0057 (8)
C40.0523 (11)0.0593 (12)0.0703 (12)−0.0002 (9)0.0354 (10)0.0096 (10)
C50.0653 (13)0.0683 (13)0.0807 (15)0.0140 (11)0.0436 (12)0.0243 (12)
C60.0563 (12)0.0908 (16)0.0562 (11)0.0201 (11)0.0308 (10)0.0193 (11)
C70.0533 (11)0.0786 (14)0.0473 (10)0.0022 (10)0.0250 (9)−0.0035 (10)
C80.0529 (10)0.0559 (10)0.0445 (9)0.0026 (8)0.0273 (9)0.0014 (8)
C90.0408 (9)0.0534 (10)0.0433 (9)−0.0030 (7)0.0242 (8)−0.0071 (7)
C100.0587 (12)0.0980 (16)0.0542 (11)0.0093 (12)0.0349 (10)0.0124 (11)
C110.0525 (12)0.0875 (15)0.0519 (11)0.0106 (10)0.0226 (10)0.0141 (11)
C120.0395 (10)0.0748 (13)0.0626 (12)0.0098 (9)0.0227 (9)0.0021 (10)
C130.0409 (9)0.0652 (11)0.0542 (10)−0.0010 (8)0.0280 (8)−0.0045 (9)
C140.0375 (9)0.0542 (10)0.0400 (8)−0.0046 (7)0.0210 (7)0.0040 (7)
C150.0403 (9)0.0629 (11)0.0487 (10)−0.0006 (8)0.0245 (8)0.0053 (8)
C160.0403 (10)0.0791 (14)0.0584 (11)0.0024 (9)0.0277 (9)0.0208 (10)
C170.0481 (11)0.0823 (15)0.0605 (12)−0.0146 (10)0.0237 (10)0.0190 (11)
C180.0746 (14)0.0596 (12)0.0589 (12)−0.0203 (10)0.0292 (11)−0.0003 (10)
C190.0645 (12)0.0581 (11)0.0536 (11)−0.0049 (9)0.0344 (10)0.0005 (9)
C200.0799 (17)0.123 (2)0.132 (2)0.0221 (16)0.0802 (18)0.047 (2)
N10.0420 (8)0.0610 (9)0.0584 (9)−0.0034 (7)0.0304 (7)−0.0005 (8)
N20.0450 (8)0.0583 (9)0.0599 (9)−0.0028 (7)0.0314 (8)0.0045 (7)
N30.0379 (7)0.0515 (8)0.0450 (7)−0.0017 (6)0.0249 (6)0.0015 (6)
N40.0491 (9)0.0881 (12)0.0516 (9)0.0111 (8)0.0313 (8)0.0086 (8)

Geometric parameters (Å, °)

C1—N21.317 (2)C11—C121.368 (3)
C1—N31.369 (2)C11—H110.9300
C1—C31.470 (2)C12—C131.375 (3)
C2—N11.310 (2)C12—H120.9300
C2—N31.368 (2)C13—H130.9300
C2—C91.472 (2)C14—C191.375 (3)
C3—C81.383 (3)C14—C151.379 (2)
C3—C41.393 (3)C14—N31.444 (2)
C4—C51.379 (3)C15—C161.388 (2)
C4—H40.9300C15—H150.9300
C5—C61.373 (3)C16—C171.381 (3)
C5—H50.9300C16—C201.504 (3)
C6—C71.375 (3)C17—C181.375 (3)
C6—H60.9300C17—H170.9300
C7—C81.375 (3)C18—C191.390 (3)
C7—H70.9300C18—H180.9300
C8—H80.9300C19—H190.9300
C9—N41.346 (2)C20—H20A0.9600
C9—C131.384 (2)C20—H20B0.9600
C10—N41.335 (3)C20—H20C0.9600
C10—C111.383 (3)N1—N21.387 (2)
C10—H100.9300
N2—C1—N3110.12 (15)C13—C12—H12120.5
N2—C1—C3123.56 (16)C12—C13—C9119.16 (18)
N3—C1—C3126.29 (15)C12—C13—H13120.4
N1—C2—N3110.15 (15)C9—C13—H13120.4
N1—C2—C9123.91 (15)C19—C14—C15121.67 (16)
N3—C2—C9125.86 (15)C19—C14—N3119.22 (16)
C8—C3—C4118.92 (17)C15—C14—N3119.10 (16)
C8—C3—C1122.00 (17)C14—C15—C16120.07 (19)
C4—C3—C1119.04 (17)C14—C15—H15120.0
C5—C4—C3120.3 (2)C16—C15—H15120.0
C5—C4—H4119.9C17—C16—C15117.99 (19)
C3—C4—H4119.9C17—C16—C20121.9 (2)
C6—C5—C4120.2 (2)C15—C16—C20120.1 (2)
C6—C5—H5119.9C18—C17—C16122.09 (18)
C4—C5—H5119.9C18—C17—H17119.0
C5—C6—C7119.64 (19)C16—C17—H17119.0
C5—C6—H6120.2C17—C18—C19119.6 (2)
C7—C6—H6120.2C17—C18—H18120.2
C8—C7—C6120.8 (2)C19—C18—H18120.2
C8—C7—H7119.6C14—C19—C18118.5 (2)
C6—C7—H7119.6C14—C19—H19120.7
C7—C8—C3120.15 (19)C18—C19—H19120.7
C7—C8—H8119.9C16—C20—H20A109.5
C3—C8—H8119.9C16—C20—H20B109.5
N4—C9—C13122.49 (17)H20A—C20—H20B109.5
N4—C9—C2116.73 (15)C16—C20—H20C109.5
C13—C9—C2120.72 (16)H20A—C20—H20C109.5
N4—C10—C11123.52 (19)H20B—C20—H20C109.5
N4—C10—H10118.2C2—N1—N2107.66 (14)
C11—C10—H10118.2C1—N2—N1107.09 (14)
C12—C11—C10118.65 (19)C2—N3—C1104.97 (13)
C12—C11—H11120.7C2—N3—C14127.64 (14)
C10—C11—H11120.7C1—N3—C14127.40 (13)
C11—C12—C13119.03 (18)C10—N4—C9117.14 (16)
C11—C12—H12120.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C12—H12···N2i0.932.603.375 (3)142
C20—H20A···N2ii0.962.623.549 (4)163
C10—H10···Cg1ii0.932.723.646 (3)175

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2238).

References

  • Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
  • Huang, L., Wang, Z., Zhang, X. & Wu, P. (2008). Acta Cryst. E64, m741–m742. [PMC free article] [PubMed]
  • Klingsberg, E. (1958). J. Org. Chem 23, 1086–1087.
  • Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Z.-X., Lan, Y., Yuan, L.-T. & Liu, C.-Y. (2005). Acta Cryst. E61, o2033–o2034.

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