The title compound, C
13H
10N
4, 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
CCDC reference: 259565
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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-4
H-1,2,4-triazole
top
Crystal data top
C13H10N4 | F(000) = 464 |
Mr = 222.25 | Dx = 1.380 Mg m−3 |
Monoclinic, P21/n | Melting point: 475 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.54178 Å |
a = 9.165 (2) Å | Cell parameters from 58 reflections |
b = 12.030 (4) Å | θ = 6–15° |
c = 9.812 (4) Å | µ = 0.70 mm−1 |
β = 98.69 (3)° | T = 293 K |
V = 1069.4 (6) Å3 | Plate, orange |
Z = 4 | 0.54 × 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 tube | Rint = 0 |
Graphite monochromator | θmax = 75.1°, θmin = 5.9° |
ω–2θ scans | h = −11→11 |
Absorption correction: numerical (KM-4 Software; Kuma, 1998) | k = 0→15 |
Tmin = 0.706, Tmax = 0.988 | l = 0→12 |
2210 measured reflections | 3 standard reflections every 100 reflections |
2210 independent reflections | intensity decay: 3.0% |
Refinement top
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.4382 (3) | 0.4825 (2) | 0.2858 (3) | 0.0604 (8) | |
N2 | 0.3671 (3) | 0.3916 (2) | 0.3369 (3) | 0.0545 (7) | |
C3 | 0.4703 (3) | 0.3284 (2) | 0.4059 (3) | 0.0426 (8) | |
N4 | 0.6066 (2) | 0.3734 (2) | 0.4020 (2) | 0.0423 (7) | |
C5 | 0.5791 (4) | 0.4677 (3) | 0.3262 (3) | 0.0556 (9) | |
H5 | 0.6520 | 0.5160 | 0.3057 | 0.067* | |
N1P | 0.3725 (3) | 0.0411 (2) | 0.6306 (3) | 0.0542 (8) | |
C2P | 0.4694 (4) | 0.1180 (3) | 0.6853 (3) | 0.0570 (9) | |
H2P | 0.5147 | 0.1079 | 0.7759 | 0.068* | |
C3P | 0.5066 (3) | 0.2109 (3) | 0.6164 (3) | 0.0500 (8) | |
H3P | 0.5753 | 0.2614 | 0.6598 | 0.060* | |
C4P | 0.4408 (3) | 0.2282 (2) | 0.4829 (3) | 0.0408 (8) | |
C5P | 0.3414 (3) | 0.1492 (3) | 0.4237 (3) | 0.0452 (8) | |
H5P | 0.2947 | 0.1577 | 0.3334 | 0.054* | |
C6P | 0.3120 (3) | 0.0579 (3) | 0.4999 (4) | 0.0529 (9) | |
H6P | 0.2461 | 0.0050 | 0.4577 | 0.063* | |
C1F | 0.7509 (3) | 0.3315 (3) | 0.4593 (3) | 0.0403 (7) | |
C2F | 0.7929 (3) | 0.2264 (3) | 0.4240 (3) | 0.0489 (8) | |
H2F | 0.7280 | 0.1816 | 0.3662 | 0.059* | |
C3F | 0.9329 (4) | 0.1889 (3) | 0.4757 (3) | 0.0547 (9) | |
H3F | 0.9630 | 0.1183 | 0.4531 | 0.066* | |
C4F | 1.0280 (3) | 0.2569 (3) | 0.5612 (3) | 0.0513 (9) | |
H4F | 1.1224 | 0.2319 | 0.5958 | 0.062* | |
C5F | 0.9843 (3) | 0.3603 (3) | 0.5951 (3) | 0.0495 (8) | |
H5F | 1.0492 | 0.4054 | 0.6525 | 0.059* | |
C6F | 0.8443 (3) | 0.3986 (3) | 0.5448 (3) | 0.0470 (8) | |
H6F | 0.8142 | 0.4689 | 0.5686 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0574 (18) | 0.0577 (18) | 0.0630 (19) | 0.0097 (16) | −0.0004 (15) | 0.0132 (16) |
N2 | 0.0495 (15) | 0.0555 (17) | 0.0554 (19) | 0.0055 (15) | −0.0024 (13) | 0.0053 (15) |
C3 | 0.0405 (18) | 0.0451 (19) | 0.041 (2) | 0.0005 (16) | 0.0022 (15) | −0.0018 (16) |
N4 | 0.0423 (14) | 0.0402 (15) | 0.0438 (16) | 0.0022 (13) | 0.0045 (13) | 0.0044 (12) |
C5 | 0.062 (2) | 0.0427 (19) | 0.061 (2) | −0.001 (2) | 0.0073 (18) | 0.0106 (19) |
N1P | 0.0503 (17) | 0.0519 (18) | 0.060 (2) | −0.0039 (14) | 0.0058 (15) | 0.0044 (15) |
C2P | 0.060 (2) | 0.062 (2) | 0.046 (2) | 0.000 (2) | 0.0013 (18) | 0.004 (2) |
C3P | 0.052 (2) | 0.052 (2) | 0.044 (2) | −0.0107 (18) | −0.0003 (16) | 0.0007 (17) |
C4P | 0.0343 (17) | 0.046 (2) | 0.043 (2) | 0.0024 (15) | 0.0066 (14) | 0.0018 (16) |
C5P | 0.0386 (17) | 0.055 (2) | 0.041 (2) | 0.0040 (16) | 0.0016 (14) | −0.0019 (17) |
C6P | 0.0412 (19) | 0.051 (2) | 0.065 (3) | −0.0056 (17) | 0.0017 (18) | −0.0044 (19) |
C1F | 0.0352 (16) | 0.0444 (18) | 0.0413 (18) | 0.0023 (16) | 0.0063 (13) | 0.0025 (16) |
C2F | 0.0508 (19) | 0.0441 (18) | 0.050 (2) | −0.0026 (17) | 0.0007 (16) | −0.0074 (16) |
C3F | 0.054 (2) | 0.045 (2) | 0.064 (3) | 0.0082 (18) | 0.0083 (18) | −0.0024 (18) |
C4F | 0.0405 (18) | 0.060 (2) | 0.053 (2) | 0.0046 (19) | 0.0055 (16) | 0.003 (2) |
C5F | 0.0436 (19) | 0.052 (2) | 0.052 (2) | −0.0026 (17) | 0.0019 (15) | −0.0080 (16) |
C6F | 0.0502 (19) | 0.0405 (18) | 0.051 (2) | −0.0010 (16) | 0.0089 (17) | −0.0061 (16) |
Geometric parameters (Å, º) top
N1—C5 | 1.304 (4) | C5P—C6P | 1.378 (4) |
N1—N2 | 1.404 (3) | C5P—H5P | 0.9300 |
N2—C3 | 1.318 (3) | C6P—H6P | 0.9300 |
C3—N4 | 1.367 (3) | C1F—C6F | 1.368 (4) |
C3—C4P | 1.469 (4) | C1F—C2F | 1.381 (4) |
N4—C5 | 1.360 (3) | C2F—C3F | 1.382 (4) |
N4—C1F | 1.448 (3) | C2F—H2F | 0.9300 |
C5—H5 | 0.9300 | C3F—C4F | 1.382 (4) |
N1P—C6P | 1.333 (4) | C3F—H3F | 0.9300 |
N1P—C2P | 1.338 (3) | C4F—C5F | 1.363 (4) |
C2P—C3P | 1.376 (4) | C4F—H4F | 0.9300 |
C2P—H2P | 0.9300 | C5F—C6F | 1.382 (4) |
C3P—C4P | 1.373 (4) | C5F—H5F | 0.9300 |
C3P—H3P | 0.9300 | C6F—H6F | 0.9300 |
C4P—C5P | 1.382 (4) | | |
| | | |
C5—N1—N2 | 106.1 (3) | C4P—C5P—H5P | 120.3 |
C3—N2—N1 | 107.3 (2) | N1P—C6P—C5P | 123.7 (3) |
N2—C3—N4 | 110.2 (3) | N1P—C6P—H6P | 118.1 |
N2—C3—C4P | 124.3 (3) | C5P—C6P—H6P | 118.1 |
N4—C3—C4P | 125.4 (3) | C6F—C1F—C2F | 121.5 (3) |
C5—N4—C3 | 104.6 (2) | C6F—C1F—N4 | 118.9 (3) |
C5—N4—C1F | 125.9 (3) | C2F—C1F—N4 | 119.6 (3) |
C3—N4—C1F | 129.5 (2) | C1F—C2F—C3F | 119.0 (3) |
N1—C5—N4 | 111.9 (3) | C1F—C2F—H2F | 120.5 |
N1—C5—H5 | 124.1 | C3F—C2F—H2F | 120.5 |
N4—C5—H5 | 124.1 | C2F—C3F—C4F | 119.7 (3) |
C6P—N1P—C2P | 115.8 (3) | C2F—C3F—H3F | 120.2 |
N1P—C2P—C3P | 124.3 (3) | C4F—C3F—H3F | 120.2 |
N1P—C2P—H2P | 117.9 | C5F—C4F—C3F | 120.4 (3) |
C3P—C2P—H2P | 117.9 | C5F—C4F—H4F | 119.8 |
C4P—C3P—C2P | 119.1 (3) | C3F—C4F—H4F | 119.8 |
C4P—C3P—H3P | 120.4 | C4F—C5F—C6F | 120.6 (3) |
C2P—C3P—H3P | 120.4 | C4F—C5F—H5F | 119.7 |
C3P—C4P—C5P | 117.6 (3) | C6F—C5F—H5F | 119.7 |
C3P—C4P—C3 | 121.8 (3) | C1F—C6F—C5F | 118.9 (3) |
C5P—C4P—C3 | 120.6 (3) | C1F—C6F—H6F | 120.6 |
C6P—C5P—C4P | 119.4 (3) | C5F—C6F—H6F | 120.6 |
C6P—C5P—H5P | 120.3 | | |
| | | |
C5—N1—N2—C3 | 0.5 (3) | N4—C3—C4P—C5P | −137.0 (3) |
N1—N2—C3—N4 | −0.3 (3) | C3P—C4P—C5P—C6P | 0.3 (4) |
N1—N2—C3—C4P | 176.1 (3) | C3—C4P—C5P—C6P | −177.8 (3) |
N2—C3—N4—C5 | 0.0 (3) | C2P—N1P—C6P—C5P | −1.8 (5) |
C4P—C3—N4—C5 | −176.3 (3) | C4P—C5P—C6P—N1P | 1.2 (5) |
N2—C3—N4—C1F | −177.9 (3) | C5—N4—C1F—C6F | 56.3 (4) |
C4P—C3—N4—C1F | 5.8 (5) | C3—N4—C1F—C6F | −126.2 (3) |
N2—N1—C5—N4 | −0.5 (4) | C5—N4—C1F—C2F | −121.9 (3) |
C3—N4—C5—N1 | 0.4 (4) | C3—N4—C1F—C2F | 55.5 (4) |
C1F—N4—C5—N1 | 178.4 (3) | C6F—C1F—C2F—C3F | −0.4 (5) |
C6P—N1P—C2P—C3P | 1.0 (5) | N4—C1F—C2F—C3F | 177.8 (3) |
N1P—C2P—C3P—C4P | 0.4 (5) | C1F—C2F—C3F—C4F | −0.1 (5) |
C2P—C3P—C4P—C5P | −1.0 (4) | C2F—C3F—C4F—C5F | 0.3 (5) |
C2P—C3P—C4P—C3 | 177.0 (3) | C3F—C4F—C5F—C6F | 0.1 (5) |
N2—C3—C4P—C3P | −130.7 (3) | C2F—C1F—C6F—C5F | 0.8 (5) |
N4—C3—C4P—C3P | 45.1 (4) | N4—C1F—C6F—C5F | −177.4 (3) |
N2—C3—C4P—C5P | 47.2 (4) | C4F—C5F—C6F—C1F | −0.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N1pi | 0.93 | 2.93 | 3.534 (4) | 124 |
C6f—H6f···N2ii | 0.93 | 2.63 | 3.486 (4) | 154 |
C6f—H6f···N1ii | 0.93 | 2.96 | 3.580 (4) | 126 |
C2f—H2f···N1piii | 0.93 | 2.84 | 3.563 (4) | 136 |
C5f—H5f···N1piv | 0.93 | 2.69 | 3.554 (4) | 155 |
C6p—H6p···N1v | 0.93 | 2.72 | 3.464 (4) | 137 |
C4f—H4f···πvi | 0.93 | 2.94 | 3.782 (4) | 151 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (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, y−1/2, −z+1/2; (vi) x+1, y, z. |