Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032990/om2137sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032990/om2137Isup2.hkl |
CCDC reference: 657732
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.053
- wR factor = 0.164
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc. PLAT230_ALERT_2_B Hirshfeld Test Diff for C15A - C18A .. 7.21 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15B 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 H8A .. N1B .. 2.83 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. N2B .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A .. N6A .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H18B .. N1A .. 2.87 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A .. N2B .. 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B .. N6A .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B .. N1A .. 2.68 Ang. PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P
Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
3,4-Diaryl-1,2,4-triazole derivatives have been reported by Mazur et al. (2004a,b), Chinnakali et al. (1999) and Rogers et al. (1990). For pyridine C—H···N interactions see also Mootz & Wussow (1981).
For related literature, see: Modzelewska (1991/1992).
The title compound was synthesized according to a literature method (Modzelewska, 1991/1992) in reaction of N3-substituted amidrazone with diethylethoxymethylene malonate. Needle-shaped orange single crystals, suitable for X-ray diffraction measurements, were obtained by recrystallization from methanol at room temperature. The melting point determined on a Boëtius microscope was 392 K.
All H atoms were positioned geometrically and constrained, with C—H bond distances of 0.93 and 0.96Å for aromatic and methylene H atom, respectively. The displacement parameters of the H atoms were Uiso(H) = 1.2 Ueq(C).
As an extension of our work on the structural characterization of simple 1,2,4-triazole derivatives, we report here the crystal and molecular structure of 4-(4-methylphenyl)-3-(2-pyridyl)-4H-1,2,4-triazole, (I). So far, only four structures of 3,4-diaryl-1,2,4-triazole derivatives have been described in literature [refcodes: WAKBEQ, HAMSUK, GOLYUB, VEXPIX; Mazur et al. (2004a; 2004b), Chinnakali et al. (1999) and Rogers et al. (1990)].
The crystal of the title compound (Fig. 1) contains two crystallographically independent molecules in the asymmetric unit. Molecules IA and IB are related by apseudo-translation along the a axis; the vector being about a/2. Corresponding bond lengths and angles are equal within experimental errors. The central five-membered triazole rings in both molecules have planar geometry. The N1=C5 and N2=C3 bonds display double-bond character, with the bond lengths of 1.282 (4), 1.306 (3) Å for molecule IA and 1.289 (3), 1.315 (3) Å for molecule IB. The N4—C3 and N4—C5 bonds, being in the range 1.353 (3) - 1.367 (3) Å, have an intermediate character. The remaining bond lengths show no unusual values. The only significant difference between the two independent molecules is in dihedral angles between the triazole/pyridyl and triazole/phenyl rings, which are 43.9 (2)°, 44.8 (2)° (molecule IA) and 23.1 (2)°, 60.4 (3)° (molecule IB) (Fig. 2). In a closely related compounds: 4-(4-methylphenyl)-3-(4-pyridyl)-4H-1,2,4-triazole (WAKBEQ), and 4-phenyl-3-(4-pyridyl)-4H-1,2,4-triazole (HAMSUK), they were 25.2 (3)°, 67.0 (3)° and 46.8 (4)°, 55.9 (3)°, respectively.
Analysis of the intermolecular contacts reveals existence of numerous C—H···N/π and π···π interactions. The most characteristic motifs, observed in this structure, are centrosymmetric dimers created separately by the molecules IA and IB (Figs 3 and 4). Molecules forming these pairs are connected by short quite linear C5a—H5a···N1a and C5b—H5b···N1b hydrogen bonds, with interatomic C···N distances of 3.375 (3) and 3.243 (3) Å (Table 1). The same synthon [with C5···N1 distances of 3.336 (3) and 3.399 (3) Å] was observed in the structure of 3-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole (VEXPIX). The triazole N1a atom is also the acceptor in the C17b—H17b···N1a hydrogen bond. This interaction, accompanied by C11b—H11b···N6a contact, link adjacent centrosymetric dimers into tetramers. The closest distance between the central five-membered rings in neigbouring dimers indicate the existence of π···π interactions. The distances between the ring centroids of the triazole IA and IB systems are 3.687 (4) Å, with the dihedral angle between their planes of 1.0 (1) °. Other C—H···N and C—H···π hydrogen bonds are also formed and they contribute to the structure stabilization (Table 1).
3,4-Diaryl-1,2,4-triazole derivatives have been reported by Mazur et al. (2004a,b), Chinnakali et al. (1999) and Rogers et al. (1990). For pyridine C—H···N interactions see also Mootz & Wussow (1981).
For related literature, see: Modzelewska (1991/1992).
Data collection: KM-4 Software (Kuma Diffraction, 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).
C14H12N4 | Z = 4 |
Mr = 236.28 | F(000) = 496 |
Triclinic, P1 | Dx = 1.303 Mg m−3 |
Hall symbol: -P1 | Cu Kα radiation, λ = 1.54178 Å |
a = 10.730 (2) Å | Cell parameters from 40 reflections |
b = 10.929 (3) Å | θ = 7–21° |
c = 11.647 (3) Å | µ = 0.65 mm−1 |
α = 105.21 (3)° | T = 294 K |
β = 99.49 (2)° | Needle, orange |
γ = 108.34 (2)° | 0.42 × 0.28 × 0.20 mm |
V = 1204.5 (6) Å3 |
KM4 four-circle diffractometer | Rint = 0.039 |
Radiation source: fine-focus sealed tube | θmax = 80.3°, θmin = 4.5° |
Graphite monochromator | h = −13→13 |
ω–2θ scans | k = −12→12 |
5413 measured reflections | l = 0→14 |
5153 independent reflections | 3 standard reflections every 100 reflections |
1942 reflections with I > 2σ(I) | intensity decay: 0.8% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.0867P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
5153 reflections | Δρmax = 0.24 e Å−3 |
328 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0050 (7) |
C14H12N4 | γ = 108.34 (2)° |
Mr = 236.28 | V = 1204.5 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.730 (2) Å | Cu Kα radiation |
b = 10.929 (3) Å | µ = 0.65 mm−1 |
c = 11.647 (3) Å | T = 294 K |
α = 105.21 (3)° | 0.42 × 0.28 × 0.20 mm |
β = 99.49 (2)° |
KM4 four-circle diffractometer | Rint = 0.039 |
5413 measured reflections | 3 standard reflections every 100 reflections |
5153 independent reflections | intensity decay: 0.8% |
1942 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.24 e Å−3 |
5153 reflections | Δρmin = −0.20 e Å−3 |
328 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.1149 (3) | 1.0190 (3) | 0.8957 (2) | 0.0818 (7) | |
N2A | 0.1763 (3) | 1.0022 (2) | 0.7996 (2) | 0.0752 (7) | |
C3A | 0.1689 (3) | 0.8757 (3) | 0.7654 (2) | 0.0593 (7) | |
N4A | 0.1048 (2) | 0.8077 (2) | 0.83452 (18) | 0.0605 (6) | |
C5A | 0.0748 (3) | 0.9036 (3) | 0.9134 (2) | 0.0719 (8) | |
H5A | 0.0304 | 0.8873 | 0.9732 | 0.086* | |
N6A | 0.1279 (2) | 0.6903 (2) | 0.58261 (18) | 0.0600 (6) | |
C7A | 0.2148 (3) | 0.8145 (3) | 0.6605 (2) | 0.0555 (6) | |
C8A | 0.3372 (3) | 0.8835 (3) | 0.6424 (3) | 0.0646 (7) | |
H8A | 0.3949 | 0.9693 | 0.6978 | 0.078* | |
C9A | 0.3721 (3) | 0.8224 (3) | 0.5405 (3) | 0.0731 (8) | |
H9A | 0.4547 | 0.8663 | 0.5263 | 0.088* | |
C10A | 0.2861 (3) | 0.6981 (3) | 0.4608 (3) | 0.0701 (8) | |
H10A | 0.3083 | 0.6562 | 0.3910 | 0.084* | |
C11A | 0.1649 (3) | 0.6344 (3) | 0.4844 (2) | 0.0649 (7) | |
H11A | 0.1065 | 0.5487 | 0.4293 | 0.078* | |
C12A | 0.0823 (3) | 0.6717 (3) | 0.8335 (2) | 0.0562 (6) | |
C13A | 0.1852 (3) | 0.6218 (3) | 0.8270 (2) | 0.0659 (7) | |
H13A | 0.2702 | 0.6775 | 0.8253 | 0.079* | |
C14A | 0.1616 (3) | 0.4907 (3) | 0.8231 (2) | 0.0726 (8) | |
H14A | 0.2303 | 0.4567 | 0.8157 | 0.087* | |
C15A | 0.0382 (4) | 0.4071 (3) | 0.8298 (2) | 0.0708 (8) | |
C16A | −0.0622 (3) | 0.4601 (3) | 0.8402 (2) | 0.0724 (8) | |
H16A | −0.1450 | 0.4065 | 0.8477 | 0.087* | |
C17A | −0.0419 (3) | 0.5902 (3) | 0.8395 (2) | 0.0653 (7) | |
H17A | −0.1117 | 0.6231 | 0.8432 | 0.078* | |
C18A | 0.0169 (5) | 0.2674 (4) | 0.8271 (3) | 0.1151 (14) | |
H18A | −0.0729 | 0.2244 | 0.8347 | 0.138* | |
H18B | 0.0835 | 0.2696 | 0.8945 | 0.138* | |
H18C | 0.0260 | 0.2164 | 0.7503 | 0.138* | |
N1B | 0.6153 (3) | 1.0428 (3) | 0.9064 (2) | 0.0752 (7) | |
N2B | 0.6802 (2) | 1.0421 (2) | 0.8128 (2) | 0.0709 (7) | |
C3B | 0.6823 (3) | 0.9191 (3) | 0.7699 (2) | 0.0573 (6) | |
N4B | 0.6204 (2) | 0.8386 (2) | 0.83221 (19) | 0.0574 (5) | |
C5B | 0.5823 (3) | 0.9222 (3) | 0.9150 (3) | 0.0664 (7) | |
H5B | 0.5375 | 0.8956 | 0.9715 | 0.080* | |
N6B | 0.7863 (2) | 0.7749 (2) | 0.6687 (2) | 0.0620 (6) | |
C7B | 0.7465 (3) | 0.8793 (3) | 0.6717 (2) | 0.0571 (6) | |
C8B | 0.7638 (3) | 0.9491 (3) | 0.5891 (3) | 0.0719 (8) | |
H8B | 0.7340 | 1.0211 | 0.5940 | 0.086* | |
C9B | 0.8257 (3) | 0.9106 (3) | 0.4994 (3) | 0.0764 (8) | |
H9B | 0.8397 | 0.9567 | 0.4431 | 0.092* | |
C10B | 0.8663 (3) | 0.8033 (3) | 0.4946 (3) | 0.0754 (8) | |
H10B | 0.9078 | 0.7742 | 0.4344 | 0.090* | |
C11B | 0.8448 (3) | 0.7394 (3) | 0.5798 (3) | 0.0700 (8) | |
H11B | 0.8727 | 0.6663 | 0.5755 | 0.084* | |
C12B | 0.5911 (2) | 0.6965 (3) | 0.8157 (2) | 0.0524 (6) | |
C13B | 0.5098 (3) | 0.5971 (3) | 0.7054 (2) | 0.0666 (7) | |
H13B | 0.4753 | 0.6208 | 0.6395 | 0.080* | |
C14B | 0.4803 (3) | 0.4615 (3) | 0.6944 (3) | 0.0705 (8) | |
H14B | 0.4264 | 0.3943 | 0.6195 | 0.085* | |
C15B | 0.5278 (3) | 0.4222 (3) | 0.7906 (3) | 0.0644 (7) | |
C16B | 0.6077 (3) | 0.5243 (3) | 0.8987 (3) | 0.0727 (8) | |
H16B | 0.6409 | 0.5007 | 0.9652 | 0.087* | |
C17B | 0.6408 (3) | 0.6611 (3) | 0.9130 (2) | 0.0666 (7) | |
H17B | 0.6960 | 0.7282 | 0.9875 | 0.080* | |
C18B | 0.4940 (4) | 0.2749 (3) | 0.7794 (3) | 0.0997 (11) | |
H18D | 0.5056 | 0.2265 | 0.7028 | 0.120* | |
H18E | 0.4012 | 0.2350 | 0.7812 | 0.120* | |
H18F | 0.5536 | 0.2688 | 0.8470 | 0.120* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.097 (2) | 0.0727 (17) | 0.0715 (16) | 0.0414 (16) | 0.0257 (14) | 0.0042 (13) |
N2A | 0.0837 (18) | 0.0649 (16) | 0.0712 (15) | 0.0312 (13) | 0.0238 (13) | 0.0081 (12) |
C3A | 0.0594 (17) | 0.0569 (16) | 0.0549 (15) | 0.0247 (13) | 0.0127 (13) | 0.0064 (12) |
N4A | 0.0658 (15) | 0.0629 (14) | 0.0499 (11) | 0.0308 (12) | 0.0157 (11) | 0.0063 (10) |
C5A | 0.082 (2) | 0.077 (2) | 0.0556 (15) | 0.0389 (17) | 0.0246 (15) | 0.0054 (14) |
N6A | 0.0597 (14) | 0.0637 (14) | 0.0515 (12) | 0.0230 (11) | 0.0193 (11) | 0.0090 (10) |
C7A | 0.0571 (16) | 0.0565 (16) | 0.0530 (14) | 0.0250 (13) | 0.0143 (12) | 0.0143 (12) |
C8A | 0.0555 (17) | 0.0635 (17) | 0.0701 (17) | 0.0195 (14) | 0.0116 (14) | 0.0216 (14) |
C9A | 0.0603 (18) | 0.092 (2) | 0.0764 (19) | 0.0302 (18) | 0.0286 (16) | 0.0359 (18) |
C10A | 0.0701 (19) | 0.095 (2) | 0.0597 (16) | 0.0442 (18) | 0.0280 (15) | 0.0268 (16) |
C11A | 0.077 (2) | 0.0669 (17) | 0.0510 (14) | 0.0335 (15) | 0.0223 (14) | 0.0092 (13) |
C12A | 0.0604 (16) | 0.0653 (17) | 0.0412 (12) | 0.0273 (14) | 0.0149 (12) | 0.0101 (11) |
C13A | 0.0654 (18) | 0.075 (2) | 0.0611 (16) | 0.0336 (16) | 0.0160 (14) | 0.0209 (14) |
C14A | 0.081 (2) | 0.086 (2) | 0.0563 (16) | 0.0413 (18) | 0.0171 (15) | 0.0220 (15) |
C15A | 0.101 (3) | 0.0659 (19) | 0.0439 (14) | 0.0323 (18) | 0.0156 (15) | 0.0168 (12) |
C16A | 0.077 (2) | 0.084 (2) | 0.0523 (15) | 0.0225 (17) | 0.0209 (14) | 0.0232 (15) |
C17A | 0.0659 (18) | 0.082 (2) | 0.0483 (14) | 0.0320 (16) | 0.0189 (13) | 0.0146 (13) |
C18A | 0.154 (4) | 0.092 (3) | 0.092 (3) | 0.035 (3) | 0.031 (3) | 0.033 (2) |
N1B | 0.0827 (18) | 0.0697 (17) | 0.0814 (16) | 0.0419 (14) | 0.0315 (14) | 0.0164 (13) |
N2B | 0.0688 (16) | 0.0634 (15) | 0.0861 (17) | 0.0317 (13) | 0.0259 (14) | 0.0225 (13) |
C3B | 0.0567 (16) | 0.0567 (16) | 0.0619 (15) | 0.0266 (13) | 0.0178 (13) | 0.0179 (12) |
N4B | 0.0634 (14) | 0.0603 (14) | 0.0557 (12) | 0.0322 (11) | 0.0214 (10) | 0.0166 (10) |
C5B | 0.0747 (19) | 0.0677 (19) | 0.0667 (16) | 0.0385 (16) | 0.0294 (15) | 0.0174 (14) |
N6B | 0.0606 (13) | 0.0645 (14) | 0.0703 (14) | 0.0307 (12) | 0.0259 (11) | 0.0235 (11) |
C7B | 0.0528 (15) | 0.0573 (16) | 0.0599 (15) | 0.0218 (13) | 0.0139 (12) | 0.0172 (12) |
C8B | 0.069 (2) | 0.080 (2) | 0.0763 (19) | 0.0324 (16) | 0.0207 (16) | 0.0344 (16) |
C9B | 0.0662 (19) | 0.097 (2) | 0.0742 (19) | 0.0267 (18) | 0.0262 (16) | 0.0413 (18) |
C10B | 0.0623 (19) | 0.096 (2) | 0.0659 (18) | 0.0261 (17) | 0.0258 (15) | 0.0225 (16) |
C11B | 0.0616 (18) | 0.0711 (19) | 0.083 (2) | 0.0304 (15) | 0.0315 (16) | 0.0209 (15) |
C12B | 0.0547 (15) | 0.0554 (15) | 0.0531 (14) | 0.0263 (13) | 0.0196 (12) | 0.0176 (12) |
C13B | 0.0665 (18) | 0.0672 (18) | 0.0590 (16) | 0.0230 (15) | 0.0070 (14) | 0.0189 (14) |
C14B | 0.068 (2) | 0.0587 (18) | 0.0703 (18) | 0.0147 (15) | 0.0133 (15) | 0.0133 (14) |
C15B | 0.0644 (19) | 0.0634 (17) | 0.0708 (17) | 0.0250 (15) | 0.0269 (15) | 0.0247 (14) |
C16B | 0.087 (2) | 0.075 (2) | 0.0647 (18) | 0.0337 (17) | 0.0207 (16) | 0.0332 (15) |
C17B | 0.075 (2) | 0.0691 (18) | 0.0546 (15) | 0.0292 (15) | 0.0163 (14) | 0.0175 (13) |
C18B | 0.108 (3) | 0.071 (2) | 0.128 (3) | 0.030 (2) | 0.046 (2) | 0.042 (2) |
N1A—C5A | 1.282 (4) | N1B—C5B | 1.289 (3) |
N1A—N2A | 1.390 (3) | N1B—N2B | 1.386 (3) |
N2A—C3A | 1.306 (3) | N2B—C3B | 1.315 (3) |
C3A—N4A | 1.360 (3) | C3B—N4B | 1.367 (3) |
C3A—C7A | 1.470 (3) | C3B—C7B | 1.468 (3) |
N4A—C5A | 1.360 (3) | N4B—C5B | 1.353 (3) |
N4A—C12A | 1.425 (3) | N4B—C12B | 1.437 (3) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
N6A—C11A | 1.332 (3) | N6B—C11B | 1.331 (3) |
N6A—C7A | 1.347 (3) | N6B—C7B | 1.333 (3) |
C7A—C8A | 1.374 (4) | C7B—C8B | 1.378 (4) |
C8A—C9A | 1.373 (4) | C8B—C9B | 1.372 (4) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.351 (4) | C9B—C10B | 1.365 (4) |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C11A | 1.378 (4) | C10B—C11B | 1.365 (4) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C17A | 1.375 (4) | C12B—C17B | 1.372 (3) |
C12A—C13A | 1.381 (3) | C12B—C13B | 1.376 (3) |
C13A—C14A | 1.361 (4) | C13B—C14B | 1.380 (4) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.381 (4) | C14B—C15B | 1.379 (4) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.381 (4) | C15B—C16B | 1.368 (4) |
C15A—C18A | 1.462 (4) | C15B—C18B | 1.499 (4) |
C16A—C17A | 1.372 (4) | C16B—C17B | 1.379 (4) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—H18A | 0.9600 | C18B—H18D | 0.9600 |
C18A—H18B | 0.9600 | C18B—H18E | 0.9600 |
C18A—H18C | 0.9600 | C18B—H18F | 0.9600 |
C5A—N1A—N2A | 106.6 (2) | C5B—N1B—N2B | 106.5 (2) |
C3A—N2A—N1A | 107.1 (2) | C3B—N2B—N1B | 107.3 (2) |
N2A—C3A—N4A | 110.6 (2) | N2B—C3B—N4B | 109.9 (2) |
N2A—C3A—C7A | 123.9 (3) | N2B—C3B—C7B | 123.6 (2) |
N4A—C3A—C7A | 125.3 (2) | N4B—C3B—C7B | 126.5 (2) |
C3A—N4A—C5A | 103.7 (2) | C5B—N4B—C3B | 104.1 (2) |
C3A—N4A—C12A | 129.2 (2) | C5B—N4B—C12B | 124.7 (2) |
C5A—N4A—C12A | 126.9 (2) | C3B—N4B—C12B | 131.1 (2) |
N1A—C5A—N4A | 112.1 (3) | N1B—C5B—N4B | 112.2 (3) |
N1A—C5A—H5A | 123.9 | N1B—C5B—H5B | 123.9 |
N4A—C5A—H5A | 123.9 | N4B—C5B—H5B | 123.9 |
C11A—N6A—C7A | 117.1 (2) | C11B—N6B—C7B | 116.4 (2) |
N6A—C7A—C8A | 123.0 (2) | N6B—C7B—C8B | 123.2 (2) |
N6A—C7A—C3A | 115.8 (2) | N6B—C7B—C3B | 116.6 (2) |
C8A—C7A—C3A | 121.2 (2) | C8B—C7B—C3B | 120.2 (2) |
C9A—C8A—C7A | 118.3 (3) | C9B—C8B—C7B | 118.8 (3) |
C9A—C8A—H8A | 120.9 | C9B—C8B—H8B | 120.6 |
C7A—C8A—H8A | 120.9 | C7B—C8B—H8B | 120.6 |
C10A—C9A—C8A | 119.7 (3) | C10B—C9B—C8B | 118.7 (3) |
C10A—C9A—H9A | 120.1 | C10B—C9B—H9B | 120.7 |
C8A—C9A—H9A | 120.1 | C8B—C9B—H9B | 120.7 |
C9A—C10A—C11A | 119.1 (3) | C11B—C10B—C9B | 118.6 (3) |
C9A—C10A—H10A | 120.5 | C11B—C10B—H10B | 120.7 |
C11A—C10A—H10A | 120.5 | C9B—C10B—H10B | 120.7 |
N6A—C11A—C10A | 122.9 (3) | N6B—C11B—C10B | 124.3 (3) |
N6A—C11A—H11A | 118.6 | N6B—C11B—H11B | 117.9 |
C10A—C11A—H11A | 118.6 | C10B—C11B—H11B | 117.9 |
C17A—C12A—C13A | 119.9 (3) | C17B—C12B—C13B | 120.4 (3) |
C17A—C12A—N4A | 120.0 (3) | C17B—C12B—N4B | 119.1 (2) |
C13A—C12A—N4A | 120.1 (3) | C13B—C12B—N4B | 120.5 (2) |
C14A—C13A—C12A | 119.7 (3) | C12B—C13B—C14B | 118.9 (3) |
C14A—C13A—H13A | 120.2 | C12B—C13B—H13B | 120.6 |
C12A—C13A—H13A | 120.2 | C14B—C13B—H13B | 120.6 |
C13A—C14A—C15A | 121.5 (3) | C15B—C14B—C13B | 122.3 (3) |
C13A—C14A—H14A | 119.2 | C15B—C14B—H14B | 118.9 |
C15A—C14A—H14A | 119.2 | C13B—C14B—H14B | 118.9 |
C14A—C15A—C16A | 118.0 (3) | C16B—C15B—C14B | 117.0 (3) |
C14A—C15A—C18A | 120.2 (3) | C16B—C15B—C18B | 120.7 (3) |
C16A—C15A—C18A | 121.8 (3) | C14B—C15B—C18B | 122.3 (3) |
C17A—C16A—C15A | 121.2 (3) | C15B—C16B—C17B | 122.5 (3) |
C17A—C16A—H16A | 119.4 | C15B—C16B—H16B | 118.7 |
C15A—C16A—H16A | 119.4 | C17B—C16B—H16B | 118.7 |
C16A—C17A—C12A | 119.6 (3) | C12B—C17B—C16B | 119.0 (3) |
C16A—C17A—H17A | 120.2 | C12B—C17B—H17B | 120.5 |
C12A—C17A—H17A | 120.2 | C16B—C17B—H17B | 120.5 |
C15A—C18A—H18A | 109.5 | C15B—C18B—H18D | 109.5 |
C15A—C18A—H18B | 109.5 | C15B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
C15A—C18A—H18C | 109.5 | C15B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
C5A—N1A—N2A—C3A | 0.0 (3) | C5B—N1B—N2B—C3B | 0.1 (3) |
N1A—N2A—C3A—N4A | 0.2 (3) | N1B—N2B—C3B—N4B | 0.2 (3) |
N1A—N2A—C3A—C7A | 175.9 (2) | N1B—N2B—C3B—C7B | −178.2 (2) |
N2A—C3A—N4A—C5A | −0.3 (3) | N2B—C3B—N4B—C5B | −0.3 (3) |
C7A—C3A—N4A—C5A | −176.0 (3) | C7B—C3B—N4B—C5B | 178.0 (3) |
N2A—C3A—N4A—C12A | −175.8 (3) | N2B—C3B—N4B—C12B | 176.4 (2) |
C7A—C3A—N4A—C12A | 8.5 (4) | C7B—C3B—N4B—C12B | −5.3 (4) |
N2A—N1A—C5A—N4A | −0.2 (3) | N2B—N1B—C5B—N4B | −0.3 (3) |
C3A—N4A—C5A—N1A | 0.3 (3) | C3B—N4B—C5B—N1B | 0.4 (3) |
C12A—N4A—C5A—N1A | 176.0 (3) | C12B—N4B—C5B—N1B | −176.6 (2) |
C11A—N6A—C7A—C8A | −0.1 (4) | C11B—N6B—C7B—C8B | −0.2 (4) |
C11A—N6A—C7A—C3A | 177.8 (2) | C11B—N6B—C7B—C3B | −179.8 (3) |
N2A—C3A—C7A—N6A | −133.3 (3) | N2B—C3B—C7B—N6B | 155.7 (3) |
N4A—C3A—C7A—N6A | 41.9 (4) | N4B—C3B—C7B—N6B | −22.4 (4) |
N2A—C3A—C7A—C8A | 44.7 (4) | N2B—C3B—C7B—C8B | −23.9 (4) |
N4A—C3A—C7A—C8A | −140.2 (3) | N4B—C3B—C7B—C8B | 158.1 (3) |
N6A—C7A—C8A—C9A | −0.2 (4) | N6B—C7B—C8B—C9B | −0.4 (4) |
C3A—C7A—C8A—C9A | −178.0 (2) | C3B—C7B—C8B—C9B | 179.1 (3) |
C7A—C8A—C9A—C10A | 0.5 (4) | C7B—C8B—C9B—C10B | 0.8 (5) |
C8A—C9A—C10A—C11A | −0.6 (5) | C8B—C9B—C10B—C11B | −0.6 (5) |
C7A—N6A—C11A—C10A | 0.0 (4) | C7B—N6B—C11B—C10B | 0.5 (4) |
C9A—C10A—C11A—N6A | 0.3 (5) | C9B—C10B—C11B—N6B | −0.1 (5) |
C3A—N4A—C12A—C17A | −137.7 (3) | C5B—N4B—C12B—C17B | −60.9 (3) |
C5A—N4A—C12A—C17A | 47.7 (4) | C3B—N4B—C12B—C17B | 123.0 (3) |
C3A—N4A—C12A—C13A | 42.7 (4) | C5B—N4B—C12B—C13B | 116.6 (3) |
C5A—N4A—C12A—C13A | −132.0 (3) | C3B—N4B—C12B—C13B | −59.6 (4) |
C17A—C12A—C13A—C14A | 1.9 (4) | C17B—C12B—C13B—C14B | −0.5 (4) |
N4A—C12A—C13A—C14A | −178.4 (2) | N4B—C12B—C13B—C14B | −177.9 (2) |
C12A—C13A—C14A—C15A | −2.3 (4) | C12B—C13B—C14B—C15B | 1.0 (4) |
C13A—C14A—C15A—C16A | 0.3 (4) | C13B—C14B—C15B—C16B | −0.6 (4) |
C13A—C14A—C15A—C18A | −179.1 (3) | C13B—C14B—C15B—C18B | 179.0 (3) |
C14A—C15A—C16A—C17A | 2.2 (4) | C14B—C15B—C16B—C17B | −0.2 (4) |
C18A—C15A—C16A—C17A | −178.4 (3) | C18B—C15B—C16B—C17B | −179.8 (3) |
C15A—C16A—C17A—C12A | −2.6 (4) | C13B—C12B—C17B—C16B | −0.2 (4) |
C13A—C12A—C17A—C16A | 0.6 (4) | N4B—C12B—C17B—C16B | 177.2 (2) |
N4A—C12A—C17A—C16A | −179.1 (2) | C15B—C16B—C17B—C12B | 0.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8a—H8a···N1b | 0.93 | 2.83 | 3.502 (3) | 130 |
C8a—H8a···N2b | 0.93 | 2.89 | 3.502 (3) | 125 |
C5a—H5a···N1ai | 0.93 | 2.60 | 3.376 (3) | 141 |
C11a—H11a···N6aii | 0.93 | 2.96 | 3.715 (3) | 140 |
C18a—H18b···N1aiii | 0.96 | 2.87 | 3.432 (4) | 119 |
C5b—H5b···N1biv | 0.93 | 2.48 | 3.244 (3) | 140 |
C14b—H14b···πv | 0.93 | 3.05 | 3.951 (4) | 164 |
C18a—H18a···N2bvi | 0.96 | 2.69 | 3.623 (3) | 164 |
C11b—H11b···N6avii | 0.93 | 2.65 | 3.243 (3) | 122 |
C17b—H17b···N1aiv | 0.93 | 2.68 | 3.505 (4) | 148 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, −y+1, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+2, −z+2; (v) −x+1, −y+1, −z+1; (vi) x−1, y−1, z; (vii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C14H12N4 |
Mr | 236.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 10.730 (2), 10.929 (3), 11.647 (3) |
α, β, γ (°) | 105.21 (3), 99.49 (2), 108.34 (2) |
V (Å3) | 1204.5 (6) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.42 × 0.28 × 0.20 |
Data collection | |
Diffractometer | KM4 four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5413, 5153, 1942 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.164, 0.96 |
No. of reflections | 5153 |
No. of parameters | 328 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.20 |
Computer programs: KM-4 Software (Kuma Diffraction, 1998), KM-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXL97 and enCIFer (Allen et al., 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
C8a—H8a···N1b | 0.93 | 2.83 | 3.502 (3) | 130 |
C8a—H8a···N2b | 0.93 | 2.89 | 3.502 (3) | 125 |
C5a—H5a···N1ai | 0.93 | 2.60 | 3.376 (3) | 141 |
C11a—H11a···N6aii | 0.93 | 2.96 | 3.715 (3) | 140 |
C18a—H18b···N1aiii | 0.96 | 2.87 | 3.432 (4) | 119 |
C5b—H5b···N1biv | 0.93 | 2.48 | 3.244 (3) | 140 |
C14b—H14b···πv | 0.93 | 3.05 | 3.951 (4) | 164 |
C18a—H18a···N2bvi | 0.96 | 2.69 | 3.623 (3) | 164 |
C11b—H11b···N6avii | 0.93 | 2.65 | 3.243 (3) | 122 |
C17b—H17b···N1aiv | 0.93 | 2.68 | 3.505 (4) | 148 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, −y+1, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+2, −z+2; (v) −x+1, −y+1, −z+1; (vi) x−1, y−1, z; (vii) x+1, y, z. |
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As an extension of our work on the structural characterization of simple 1,2,4-triazole derivatives, we report here the crystal and molecular structure of 4-(4-methylphenyl)-3-(2-pyridyl)-4H-1,2,4-triazole, (I). So far, only four structures of 3,4-diaryl-1,2,4-triazole derivatives have been described in literature [refcodes: WAKBEQ, HAMSUK, GOLYUB, VEXPIX; Mazur et al. (2004a; 2004b), Chinnakali et al. (1999) and Rogers et al. (1990)].
The crystal of the title compound (Fig. 1) contains two crystallographically independent molecules in the asymmetric unit. Molecules IA and IB are related by apseudo-translation along the a axis; the vector being about a/2. Corresponding bond lengths and angles are equal within experimental errors. The central five-membered triazole rings in both molecules have planar geometry. The N1=C5 and N2=C3 bonds display double-bond character, with the bond lengths of 1.282 (4), 1.306 (3) Å for molecule IA and 1.289 (3), 1.315 (3) Å for molecule IB. The N4—C3 and N4—C5 bonds, being in the range 1.353 (3) - 1.367 (3) Å, have an intermediate character. The remaining bond lengths show no unusual values. The only significant difference between the two independent molecules is in dihedral angles between the triazole/pyridyl and triazole/phenyl rings, which are 43.9 (2)°, 44.8 (2)° (molecule IA) and 23.1 (2)°, 60.4 (3)° (molecule IB) (Fig. 2). In a closely related compounds: 4-(4-methylphenyl)-3-(4-pyridyl)-4H-1,2,4-triazole (WAKBEQ), and 4-phenyl-3-(4-pyridyl)-4H-1,2,4-triazole (HAMSUK), they were 25.2 (3)°, 67.0 (3)° and 46.8 (4)°, 55.9 (3)°, respectively.
Analysis of the intermolecular contacts reveals existence of numerous C—H···N/π and π···π interactions. The most characteristic motifs, observed in this structure, are centrosymmetric dimers created separately by the molecules IA and IB (Figs 3 and 4). Molecules forming these pairs are connected by short quite linear C5a—H5a···N1a and C5b—H5b···N1b hydrogen bonds, with interatomic C···N distances of 3.375 (3) and 3.243 (3) Å (Table 1). The same synthon [with C5···N1 distances of 3.336 (3) and 3.399 (3) Å] was observed in the structure of 3-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole (VEXPIX). The triazole N1a atom is also the acceptor in the C17b—H17b···N1a hydrogen bond. This interaction, accompanied by C11b—H11b···N6a contact, link adjacent centrosymetric dimers into tetramers. The closest distance between the central five-membered rings in neigbouring dimers indicate the existence of π···π interactions. The distances between the ring centroids of the triazole IA and IB systems are 3.687 (4) Å, with the dihedral angle between their planes of 1.0 (1) °. Other C—H···N and C—H···π hydrogen bonds are also formed and they contribute to the structure stabilization (Table 1).