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The title compound, C13H10N4, is a disubstituted 1,2,4-triazole derivative. The pyridyl and phenyl rings form dihedral angles of 46.7 (3) and 55.9 (4)°, respectively, with the central triazole ring. The mol­ecules in the crystal structure form two types of centrosymmetrically related dimers through hydro­phobic C—H...N and π–π intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028417/hg6100sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028417/hg6100Isup2.hkl
Contains datablock I

CCDC reference: 259565

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.057
  • wR factor = 0.126
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 32 Perc.
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. N1P .. 2.93 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6F .. N1 .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2F .. N1P .. 2.84 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5F .. N1P .. 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6P .. N1 .. 2.72 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4F .. \P .. 2.94 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C4F .. \P .. 3.78 Ang. PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... \P H4F \P PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P C4F \P PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... \P C4F H4F \P
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KM-4 Software (Kuma, 1998); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).

3-(4-pyridyl)-4-phenyl-4H-1,2,4-triazole top
Crystal data top
C13H10N4F(000) = 464
Mr = 222.25Dx = 1.380 Mg m3
Monoclinic, P21/nMelting point: 475 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54178 Å
a = 9.165 (2) ÅCell parameters from 58 reflections
b = 12.030 (4) Åθ = 6–15°
c = 9.812 (4) ŵ = 0.70 mm1
β = 98.69 (3)°T = 293 K
V = 1069.4 (6) Å3Plate, orange
Z = 40.54 × 0.21 × 0.02 mm
Data collection top
Kuma KM-4 four-circle
diffractometer
702 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0
Graphite monochromatorθmax = 75.1°, θmin = 5.9°
ω–2θ scansh = 1111
Absorption correction: numerical
(KM-4 Software; Kuma, 1998)
k = 015
Tmin = 0.706, Tmax = 0.988l = 012
2210 measured reflections3 standard reflections every 100 reflections
2210 independent reflections intensity decay: 3.0%
Refinement top
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) = 0.126H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.046P)2]
where P = (Fo2 + 2Fc2)/3
2210 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.22 e Å3
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*/Ueq
N10.4382 (3)0.4825 (2)0.2858 (3)0.0604 (8)
N20.3671 (3)0.3916 (2)0.3369 (3)0.0545 (7)
C30.4703 (3)0.3284 (2)0.4059 (3)0.0426 (8)
N40.6066 (2)0.3734 (2)0.4020 (2)0.0423 (7)
C50.5791 (4)0.4677 (3)0.3262 (3)0.0556 (9)
H50.65200.51600.30570.067*
N1P0.3725 (3)0.0411 (2)0.6306 (3)0.0542 (8)
C2P0.4694 (4)0.1180 (3)0.6853 (3)0.0570 (9)
H2P0.51470.10790.77590.068*
C3P0.5066 (3)0.2109 (3)0.6164 (3)0.0500 (8)
H3P0.57530.26140.65980.060*
C4P0.4408 (3)0.2282 (2)0.4829 (3)0.0408 (8)
C5P0.3414 (3)0.1492 (3)0.4237 (3)0.0452 (8)
H5P0.29470.15770.33340.054*
C6P0.3120 (3)0.0579 (3)0.4999 (4)0.0529 (9)
H6P0.24610.00500.45770.063*
C1F0.7509 (3)0.3315 (3)0.4593 (3)0.0403 (7)
C2F0.7929 (3)0.2264 (3)0.4240 (3)0.0489 (8)
H2F0.72800.18160.36620.059*
C3F0.9329 (4)0.1889 (3)0.4757 (3)0.0547 (9)
H3F0.96300.11830.45310.066*
C4F1.0280 (3)0.2569 (3)0.5612 (3)0.0513 (9)
H4F1.12240.23190.59580.062*
C5F0.9843 (3)0.3603 (3)0.5951 (3)0.0495 (8)
H5F1.04920.40540.65250.059*
C6F0.8443 (3)0.3986 (3)0.5448 (3)0.0470 (8)
H6F0.81420.46890.56860.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0574 (18)0.0577 (18)0.0630 (19)0.0097 (16)0.0004 (15)0.0132 (16)
N20.0495 (15)0.0555 (17)0.0554 (19)0.0055 (15)0.0024 (13)0.0053 (15)
C30.0405 (18)0.0451 (19)0.041 (2)0.0005 (16)0.0022 (15)0.0018 (16)
N40.0423 (14)0.0402 (15)0.0438 (16)0.0022 (13)0.0045 (13)0.0044 (12)
C50.062 (2)0.0427 (19)0.061 (2)0.001 (2)0.0073 (18)0.0106 (19)
N1P0.0503 (17)0.0519 (18)0.060 (2)0.0039 (14)0.0058 (15)0.0044 (15)
C2P0.060 (2)0.062 (2)0.046 (2)0.000 (2)0.0013 (18)0.004 (2)
C3P0.052 (2)0.052 (2)0.044 (2)0.0107 (18)0.0003 (16)0.0007 (17)
C4P0.0343 (17)0.046 (2)0.043 (2)0.0024 (15)0.0066 (14)0.0018 (16)
C5P0.0386 (17)0.055 (2)0.041 (2)0.0040 (16)0.0016 (14)0.0019 (17)
C6P0.0412 (19)0.051 (2)0.065 (3)0.0056 (17)0.0017 (18)0.0044 (19)
C1F0.0352 (16)0.0444 (18)0.0413 (18)0.0023 (16)0.0063 (13)0.0025 (16)
C2F0.0508 (19)0.0441 (18)0.050 (2)0.0026 (17)0.0007 (16)0.0074 (16)
C3F0.054 (2)0.045 (2)0.064 (3)0.0082 (18)0.0083 (18)0.0024 (18)
C4F0.0405 (18)0.060 (2)0.053 (2)0.0046 (19)0.0055 (16)0.003 (2)
C5F0.0436 (19)0.052 (2)0.052 (2)0.0026 (17)0.0019 (15)0.0080 (16)
C6F0.0502 (19)0.0405 (18)0.051 (2)0.0010 (16)0.0089 (17)0.0061 (16)
Geometric parameters (Å, º) top
N1—C51.304 (4)C5P—C6P1.378 (4)
N1—N21.404 (3)C5P—H5P0.9300
N2—C31.318 (3)C6P—H6P0.9300
C3—N41.367 (3)C1F—C6F1.368 (4)
C3—C4P1.469 (4)C1F—C2F1.381 (4)
N4—C51.360 (3)C2F—C3F1.382 (4)
N4—C1F1.448 (3)C2F—H2F0.9300
C5—H50.9300C3F—C4F1.382 (4)
N1P—C6P1.333 (4)C3F—H3F0.9300
N1P—C2P1.338 (3)C4F—C5F1.363 (4)
C2P—C3P1.376 (4)C4F—H4F0.9300
C2P—H2P0.9300C5F—C6F1.382 (4)
C3P—C4P1.373 (4)C5F—H5F0.9300
C3P—H3P0.9300C6F—H6F0.9300
C4P—C5P1.382 (4)
C5—N1—N2106.1 (3)C4P—C5P—H5P120.3
C3—N2—N1107.3 (2)N1P—C6P—C5P123.7 (3)
N2—C3—N4110.2 (3)N1P—C6P—H6P118.1
N2—C3—C4P124.3 (3)C5P—C6P—H6P118.1
N4—C3—C4P125.4 (3)C6F—C1F—C2F121.5 (3)
C5—N4—C3104.6 (2)C6F—C1F—N4118.9 (3)
C5—N4—C1F125.9 (3)C2F—C1F—N4119.6 (3)
C3—N4—C1F129.5 (2)C1F—C2F—C3F119.0 (3)
N1—C5—N4111.9 (3)C1F—C2F—H2F120.5
N1—C5—H5124.1C3F—C2F—H2F120.5
N4—C5—H5124.1C2F—C3F—C4F119.7 (3)
C6P—N1P—C2P115.8 (3)C2F—C3F—H3F120.2
N1P—C2P—C3P124.3 (3)C4F—C3F—H3F120.2
N1P—C2P—H2P117.9C5F—C4F—C3F120.4 (3)
C3P—C2P—H2P117.9C5F—C4F—H4F119.8
C4P—C3P—C2P119.1 (3)C3F—C4F—H4F119.8
C4P—C3P—H3P120.4C4F—C5F—C6F120.6 (3)
C2P—C3P—H3P120.4C4F—C5F—H5F119.7
C3P—C4P—C5P117.6 (3)C6F—C5F—H5F119.7
C3P—C4P—C3121.8 (3)C1F—C6F—C5F118.9 (3)
C5P—C4P—C3120.6 (3)C1F—C6F—H6F120.6
C6P—C5P—C4P119.4 (3)C5F—C6F—H6F120.6
C6P—C5P—H5P120.3
C5—N1—N2—C30.5 (3)N4—C3—C4P—C5P137.0 (3)
N1—N2—C3—N40.3 (3)C3P—C4P—C5P—C6P0.3 (4)
N1—N2—C3—C4P176.1 (3)C3—C4P—C5P—C6P177.8 (3)
N2—C3—N4—C50.0 (3)C2P—N1P—C6P—C5P1.8 (5)
C4P—C3—N4—C5176.3 (3)C4P—C5P—C6P—N1P1.2 (5)
N2—C3—N4—C1F177.9 (3)C5—N4—C1F—C6F56.3 (4)
C4P—C3—N4—C1F5.8 (5)C3—N4—C1F—C6F126.2 (3)
N2—N1—C5—N40.5 (4)C5—N4—C1F—C2F121.9 (3)
C3—N4—C5—N10.4 (4)C3—N4—C1F—C2F55.5 (4)
C1F—N4—C5—N1178.4 (3)C6F—C1F—C2F—C3F0.4 (5)
C6P—N1P—C2P—C3P1.0 (5)N4—C1F—C2F—C3F177.8 (3)
N1P—C2P—C3P—C4P0.4 (5)C1F—C2F—C3F—C4F0.1 (5)
C2P—C3P—C4P—C5P1.0 (4)C2F—C3F—C4F—C5F0.3 (5)
C2P—C3P—C4P—C3177.0 (3)C3F—C4F—C5F—C6F0.1 (5)
N2—C3—C4P—C3P130.7 (3)C2F—C1F—C6F—C5F0.8 (5)
N4—C3—C4P—C3P45.1 (4)N4—C1F—C6F—C5F177.4 (3)
N2—C3—C4P—C5P47.2 (4)C4F—C5F—C6F—C1F0.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···N1pi0.932.933.534 (4)124
C6f—H6f···N2ii0.932.633.486 (4)154
C6f—H6f···N1ii0.932.963.580 (4)126
C2f—H2f···N1piii0.932.843.563 (4)136
C5f—H5f···N1piv0.932.693.554 (4)155
C6p—H6p···N1v0.932.723.464 (4)137
C4f—H4f···πvi0.932.943.782 (4)151
Symmetry codes: (i) x+1/2, y+1/2, z1/2; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1; (iv) x+3/2, y+1/2, z+3/2; (v) x+1/2, y1/2, z+1/2; (vi) x+1, y, z.
 

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