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The crystal structure of the title compound, C14H12N4, is built from two symmetry-independent mol­ecules which are nearly related by translation by the vector a/2. The two mol­ecules exhibit almost identical bond distances and angles but they show significantly different conformations. The relative orientations of the pyridyl and benzene rings about the triazole ring are different in the two mol­ecules, and they pack differently in the crystal structure. Weak inter­molecular C—H...N, C—H...π and π...π inter­actions stabilize the crystal structure [the distance between the triazole ring centroids is 3.687 (4) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032990/om2137sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032990/om2137Isup2.hkl
Contains datablock I

CCDC reference: 657732

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Fit of the molecules IA (full lines) and IB (open lines).
[Figure 3] Fig. 3. The packing arrangement of molecules IA, viewed along the a axis. Dashed lines indicate hydrogen bonds.
[Figure 4] Fig. 4. The packing arrangement of molecules IB, viewed along the a axis. Dashed lines indicate hydrogen bonds.
4-(4-methylphenyl)-3-(2-pyridyl)-4H-1,2,4-triazole top
Crystal data top
C14H12N4Z = 4
Mr = 236.28F(000) = 496
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P1Cu Kα radiation, λ = 1.54178 Å
a = 10.730 (2) ÅCell parameters from 40 reflections
b = 10.929 (3) Åθ = 7–21°
c = 11.647 (3) ŵ = 0.65 mm1
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
Data collection top
KM4 four-circle
diffractometer
Rint = 0.039
Radiation source: fine-focus sealed tubeθmax = 80.3°, θmin = 4.5°
Graphite monochromatorh = 1313
ω–2θ scansk = 1212
5413 measured reflectionsl = 014
5153 independent reflections3 standard reflections every 100 reflections
1942 reflections with I > 2σ(I) intensity decay: 0.8%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-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 reflectionsΔρmax = 0.24 e Å3
328 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0050 (7)
Crystal data top
C14H12N4γ = 108.34 (2)°
Mr = 236.28V = 1204.5 (6) Å3
Triclinic, P1Z = 4
a = 10.730 (2) ÅCu Kα radiation
b = 10.929 (3) ŵ = 0.65 mm1
c = 11.647 (3) ÅT = 294 K
α = 105.21 (3)°0.42 × 0.28 × 0.20 mm
β = 99.49 (2)°
Data collection top
KM4 four-circle
diffractometer
Rint = 0.039
5413 measured reflections3 standard reflections every 100 reflections
5153 independent reflections intensity decay: 0.8%
1942 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 0.96Δρmax = 0.24 e Å3
5153 reflectionsΔρmin = 0.20 e Å3
328 parameters
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
N1A0.1149 (3)1.0190 (3)0.8957 (2)0.0818 (7)
N2A0.1763 (3)1.0022 (2)0.7996 (2)0.0752 (7)
C3A0.1689 (3)0.8757 (3)0.7654 (2)0.0593 (7)
N4A0.1048 (2)0.8077 (2)0.83452 (18)0.0605 (6)
C5A0.0748 (3)0.9036 (3)0.9134 (2)0.0719 (8)
H5A0.03040.88730.97320.086*
N6A0.1279 (2)0.6903 (2)0.58261 (18)0.0600 (6)
C7A0.2148 (3)0.8145 (3)0.6605 (2)0.0555 (6)
C8A0.3372 (3)0.8835 (3)0.6424 (3)0.0646 (7)
H8A0.39490.96930.69780.078*
C9A0.3721 (3)0.8224 (3)0.5405 (3)0.0731 (8)
H9A0.45470.86630.52630.088*
C10A0.2861 (3)0.6981 (3)0.4608 (3)0.0701 (8)
H10A0.30830.65620.39100.084*
C11A0.1649 (3)0.6344 (3)0.4844 (2)0.0649 (7)
H11A0.10650.54870.42930.078*
C12A0.0823 (3)0.6717 (3)0.8335 (2)0.0562 (6)
C13A0.1852 (3)0.6218 (3)0.8270 (2)0.0659 (7)
H13A0.27020.67750.82530.079*
C14A0.1616 (3)0.4907 (3)0.8231 (2)0.0726 (8)
H14A0.23030.45670.81570.087*
C15A0.0382 (4)0.4071 (3)0.8298 (2)0.0708 (8)
C16A0.0622 (3)0.4601 (3)0.8402 (2)0.0724 (8)
H16A0.14500.40650.84770.087*
C17A0.0419 (3)0.5902 (3)0.8395 (2)0.0653 (7)
H17A0.11170.62310.84320.078*
C18A0.0169 (5)0.2674 (4)0.8271 (3)0.1151 (14)
H18A0.07290.22440.83470.138*
H18B0.08350.26960.89450.138*
H18C0.02600.21640.75030.138*
N1B0.6153 (3)1.0428 (3)0.9064 (2)0.0752 (7)
N2B0.6802 (2)1.0421 (2)0.8128 (2)0.0709 (7)
C3B0.6823 (3)0.9191 (3)0.7699 (2)0.0573 (6)
N4B0.6204 (2)0.8386 (2)0.83221 (19)0.0574 (5)
C5B0.5823 (3)0.9222 (3)0.9150 (3)0.0664 (7)
H5B0.53750.89560.97150.080*
N6B0.7863 (2)0.7749 (2)0.6687 (2)0.0620 (6)
C7B0.7465 (3)0.8793 (3)0.6717 (2)0.0571 (6)
C8B0.7638 (3)0.9491 (3)0.5891 (3)0.0719 (8)
H8B0.73401.02110.59400.086*
C9B0.8257 (3)0.9106 (3)0.4994 (3)0.0764 (8)
H9B0.83970.95670.44310.092*
C10B0.8663 (3)0.8033 (3)0.4946 (3)0.0754 (8)
H10B0.90780.77420.43440.090*
C11B0.8448 (3)0.7394 (3)0.5798 (3)0.0700 (8)
H11B0.87270.66630.57550.084*
C12B0.5911 (2)0.6965 (3)0.8157 (2)0.0524 (6)
C13B0.5098 (3)0.5971 (3)0.7054 (2)0.0666 (7)
H13B0.47530.62080.63950.080*
C14B0.4803 (3)0.4615 (3)0.6944 (3)0.0705 (8)
H14B0.42640.39430.61950.085*
C15B0.5278 (3)0.4222 (3)0.7906 (3)0.0644 (7)
C16B0.6077 (3)0.5243 (3)0.8987 (3)0.0727 (8)
H16B0.64090.50070.96520.087*
C17B0.6408 (3)0.6611 (3)0.9130 (2)0.0666 (7)
H17B0.69600.72820.98750.080*
C18B0.4940 (4)0.2749 (3)0.7794 (3)0.0997 (11)
H18D0.50560.22650.70280.120*
H18E0.40120.23500.78120.120*
H18F0.55360.26880.84700.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.097 (2)0.0727 (17)0.0715 (16)0.0414 (16)0.0257 (14)0.0042 (13)
N2A0.0837 (18)0.0649 (16)0.0712 (15)0.0312 (13)0.0238 (13)0.0081 (12)
C3A0.0594 (17)0.0569 (16)0.0549 (15)0.0247 (13)0.0127 (13)0.0064 (12)
N4A0.0658 (15)0.0629 (14)0.0499 (11)0.0308 (12)0.0157 (11)0.0063 (10)
C5A0.082 (2)0.077 (2)0.0556 (15)0.0389 (17)0.0246 (15)0.0054 (14)
N6A0.0597 (14)0.0637 (14)0.0515 (12)0.0230 (11)0.0193 (11)0.0090 (10)
C7A0.0571 (16)0.0565 (16)0.0530 (14)0.0250 (13)0.0143 (12)0.0143 (12)
C8A0.0555 (17)0.0635 (17)0.0701 (17)0.0195 (14)0.0116 (14)0.0216 (14)
C9A0.0603 (18)0.092 (2)0.0764 (19)0.0302 (18)0.0286 (16)0.0359 (18)
C10A0.0701 (19)0.095 (2)0.0597 (16)0.0442 (18)0.0280 (15)0.0268 (16)
C11A0.077 (2)0.0669 (17)0.0510 (14)0.0335 (15)0.0223 (14)0.0092 (13)
C12A0.0604 (16)0.0653 (17)0.0412 (12)0.0273 (14)0.0149 (12)0.0101 (11)
C13A0.0654 (18)0.075 (2)0.0611 (16)0.0336 (16)0.0160 (14)0.0209 (14)
C14A0.081 (2)0.086 (2)0.0563 (16)0.0413 (18)0.0171 (15)0.0220 (15)
C15A0.101 (3)0.0659 (19)0.0439 (14)0.0323 (18)0.0156 (15)0.0168 (12)
C16A0.077 (2)0.084 (2)0.0523 (15)0.0225 (17)0.0209 (14)0.0232 (15)
C17A0.0659 (18)0.082 (2)0.0483 (14)0.0320 (16)0.0189 (13)0.0146 (13)
C18A0.154 (4)0.092 (3)0.092 (3)0.035 (3)0.031 (3)0.033 (2)
N1B0.0827 (18)0.0697 (17)0.0814 (16)0.0419 (14)0.0315 (14)0.0164 (13)
N2B0.0688 (16)0.0634 (15)0.0861 (17)0.0317 (13)0.0259 (14)0.0225 (13)
C3B0.0567 (16)0.0567 (16)0.0619 (15)0.0266 (13)0.0178 (13)0.0179 (12)
N4B0.0634 (14)0.0603 (14)0.0557 (12)0.0322 (11)0.0214 (10)0.0166 (10)
C5B0.0747 (19)0.0677 (19)0.0667 (16)0.0385 (16)0.0294 (15)0.0174 (14)
N6B0.0606 (13)0.0645 (14)0.0703 (14)0.0307 (12)0.0259 (11)0.0235 (11)
C7B0.0528 (15)0.0573 (16)0.0599 (15)0.0218 (13)0.0139 (12)0.0172 (12)
C8B0.069 (2)0.080 (2)0.0763 (19)0.0324 (16)0.0207 (16)0.0344 (16)
C9B0.0662 (19)0.097 (2)0.0742 (19)0.0267 (18)0.0262 (16)0.0413 (18)
C10B0.0623 (19)0.096 (2)0.0659 (18)0.0261 (17)0.0258 (15)0.0225 (16)
C11B0.0616 (18)0.0711 (19)0.083 (2)0.0304 (15)0.0315 (16)0.0209 (15)
C12B0.0547 (15)0.0554 (15)0.0531 (14)0.0263 (13)0.0196 (12)0.0176 (12)
C13B0.0665 (18)0.0672 (18)0.0590 (16)0.0230 (15)0.0070 (14)0.0189 (14)
C14B0.068 (2)0.0587 (18)0.0703 (18)0.0147 (15)0.0133 (15)0.0133 (14)
C15B0.0644 (19)0.0634 (17)0.0708 (17)0.0250 (15)0.0269 (15)0.0247 (14)
C16B0.087 (2)0.075 (2)0.0647 (18)0.0337 (17)0.0207 (16)0.0332 (15)
C17B0.075 (2)0.0691 (18)0.0546 (15)0.0292 (15)0.0163 (14)0.0175 (13)
C18B0.108 (3)0.071 (2)0.128 (3)0.030 (2)0.046 (2)0.042 (2)
Geometric parameters (Å, º) top
N1A—C5A1.282 (4)N1B—C5B1.289 (3)
N1A—N2A1.390 (3)N1B—N2B1.386 (3)
N2A—C3A1.306 (3)N2B—C3B1.315 (3)
C3A—N4A1.360 (3)C3B—N4B1.367 (3)
C3A—C7A1.470 (3)C3B—C7B1.468 (3)
N4A—C5A1.360 (3)N4B—C5B1.353 (3)
N4A—C12A1.425 (3)N4B—C12B1.437 (3)
C5A—H5A0.9300C5B—H5B0.9300
N6A—C11A1.332 (3)N6B—C11B1.331 (3)
N6A—C7A1.347 (3)N6B—C7B1.333 (3)
C7A—C8A1.374 (4)C7B—C8B1.378 (4)
C8A—C9A1.373 (4)C8B—C9B1.372 (4)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.351 (4)C9B—C10B1.365 (4)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.378 (4)C10B—C11B1.365 (4)
C10A—H10A0.9300C10B—H10B0.9300
C11A—H11A0.9300C11B—H11B0.9300
C12A—C17A1.375 (4)C12B—C17B1.372 (3)
C12A—C13A1.381 (3)C12B—C13B1.376 (3)
C13A—C14A1.361 (4)C13B—C14B1.380 (4)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.381 (4)C14B—C15B1.379 (4)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.381 (4)C15B—C16B1.368 (4)
C15A—C18A1.462 (4)C15B—C18B1.499 (4)
C16A—C17A1.372 (4)C16B—C17B1.379 (4)
C16A—H16A0.9300C16B—H16B0.9300
C17A—H17A0.9300C17B—H17B0.9300
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C5A—N1A—N2A106.6 (2)C5B—N1B—N2B106.5 (2)
C3A—N2A—N1A107.1 (2)C3B—N2B—N1B107.3 (2)
N2A—C3A—N4A110.6 (2)N2B—C3B—N4B109.9 (2)
N2A—C3A—C7A123.9 (3)N2B—C3B—C7B123.6 (2)
N4A—C3A—C7A125.3 (2)N4B—C3B—C7B126.5 (2)
C3A—N4A—C5A103.7 (2)C5B—N4B—C3B104.1 (2)
C3A—N4A—C12A129.2 (2)C5B—N4B—C12B124.7 (2)
C5A—N4A—C12A126.9 (2)C3B—N4B—C12B131.1 (2)
N1A—C5A—N4A112.1 (3)N1B—C5B—N4B112.2 (3)
N1A—C5A—H5A123.9N1B—C5B—H5B123.9
N4A—C5A—H5A123.9N4B—C5B—H5B123.9
C11A—N6A—C7A117.1 (2)C11B—N6B—C7B116.4 (2)
N6A—C7A—C8A123.0 (2)N6B—C7B—C8B123.2 (2)
N6A—C7A—C3A115.8 (2)N6B—C7B—C3B116.6 (2)
C8A—C7A—C3A121.2 (2)C8B—C7B—C3B120.2 (2)
C9A—C8A—C7A118.3 (3)C9B—C8B—C7B118.8 (3)
C9A—C8A—H8A120.9C9B—C8B—H8B120.6
C7A—C8A—H8A120.9C7B—C8B—H8B120.6
C10A—C9A—C8A119.7 (3)C10B—C9B—C8B118.7 (3)
C10A—C9A—H9A120.1C10B—C9B—H9B120.7
C8A—C9A—H9A120.1C8B—C9B—H9B120.7
C9A—C10A—C11A119.1 (3)C11B—C10B—C9B118.6 (3)
C9A—C10A—H10A120.5C11B—C10B—H10B120.7
C11A—C10A—H10A120.5C9B—C10B—H10B120.7
N6A—C11A—C10A122.9 (3)N6B—C11B—C10B124.3 (3)
N6A—C11A—H11A118.6N6B—C11B—H11B117.9
C10A—C11A—H11A118.6C10B—C11B—H11B117.9
C17A—C12A—C13A119.9 (3)C17B—C12B—C13B120.4 (3)
C17A—C12A—N4A120.0 (3)C17B—C12B—N4B119.1 (2)
C13A—C12A—N4A120.1 (3)C13B—C12B—N4B120.5 (2)
C14A—C13A—C12A119.7 (3)C12B—C13B—C14B118.9 (3)
C14A—C13A—H13A120.2C12B—C13B—H13B120.6
C12A—C13A—H13A120.2C14B—C13B—H13B120.6
C13A—C14A—C15A121.5 (3)C15B—C14B—C13B122.3 (3)
C13A—C14A—H14A119.2C15B—C14B—H14B118.9
C15A—C14A—H14A119.2C13B—C14B—H14B118.9
C14A—C15A—C16A118.0 (3)C16B—C15B—C14B117.0 (3)
C14A—C15A—C18A120.2 (3)C16B—C15B—C18B120.7 (3)
C16A—C15A—C18A121.8 (3)C14B—C15B—C18B122.3 (3)
C17A—C16A—C15A121.2 (3)C15B—C16B—C17B122.5 (3)
C17A—C16A—H16A119.4C15B—C16B—H16B118.7
C15A—C16A—H16A119.4C17B—C16B—H16B118.7
C16A—C17A—C12A119.6 (3)C12B—C17B—C16B119.0 (3)
C16A—C17A—H17A120.2C12B—C17B—H17B120.5
C12A—C17A—H17A120.2C16B—C17B—H17B120.5
C15A—C18A—H18A109.5C15B—C18B—H18D109.5
C15A—C18A—H18B109.5C15B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C15A—C18A—H18C109.5C15B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C5A—N1A—N2A—C3A0.0 (3)C5B—N1B—N2B—C3B0.1 (3)
N1A—N2A—C3A—N4A0.2 (3)N1B—N2B—C3B—N4B0.2 (3)
N1A—N2A—C3A—C7A175.9 (2)N1B—N2B—C3B—C7B178.2 (2)
N2A—C3A—N4A—C5A0.3 (3)N2B—C3B—N4B—C5B0.3 (3)
C7A—C3A—N4A—C5A176.0 (3)C7B—C3B—N4B—C5B178.0 (3)
N2A—C3A—N4A—C12A175.8 (3)N2B—C3B—N4B—C12B176.4 (2)
C7A—C3A—N4A—C12A8.5 (4)C7B—C3B—N4B—C12B5.3 (4)
N2A—N1A—C5A—N4A0.2 (3)N2B—N1B—C5B—N4B0.3 (3)
C3A—N4A—C5A—N1A0.3 (3)C3B—N4B—C5B—N1B0.4 (3)
C12A—N4A—C5A—N1A176.0 (3)C12B—N4B—C5B—N1B176.6 (2)
C11A—N6A—C7A—C8A0.1 (4)C11B—N6B—C7B—C8B0.2 (4)
C11A—N6A—C7A—C3A177.8 (2)C11B—N6B—C7B—C3B179.8 (3)
N2A—C3A—C7A—N6A133.3 (3)N2B—C3B—C7B—N6B155.7 (3)
N4A—C3A—C7A—N6A41.9 (4)N4B—C3B—C7B—N6B22.4 (4)
N2A—C3A—C7A—C8A44.7 (4)N2B—C3B—C7B—C8B23.9 (4)
N4A—C3A—C7A—C8A140.2 (3)N4B—C3B—C7B—C8B158.1 (3)
N6A—C7A—C8A—C9A0.2 (4)N6B—C7B—C8B—C9B0.4 (4)
C3A—C7A—C8A—C9A178.0 (2)C3B—C7B—C8B—C9B179.1 (3)
C7A—C8A—C9A—C10A0.5 (4)C7B—C8B—C9B—C10B0.8 (5)
C8A—C9A—C10A—C11A0.6 (5)C8B—C9B—C10B—C11B0.6 (5)
C7A—N6A—C11A—C10A0.0 (4)C7B—N6B—C11B—C10B0.5 (4)
C9A—C10A—C11A—N6A0.3 (5)C9B—C10B—C11B—N6B0.1 (5)
C3A—N4A—C12A—C17A137.7 (3)C5B—N4B—C12B—C17B60.9 (3)
C5A—N4A—C12A—C17A47.7 (4)C3B—N4B—C12B—C17B123.0 (3)
C3A—N4A—C12A—C13A42.7 (4)C5B—N4B—C12B—C13B116.6 (3)
C5A—N4A—C12A—C13A132.0 (3)C3B—N4B—C12B—C13B59.6 (4)
C17A—C12A—C13A—C14A1.9 (4)C17B—C12B—C13B—C14B0.5 (4)
N4A—C12A—C13A—C14A178.4 (2)N4B—C12B—C13B—C14B177.9 (2)
C12A—C13A—C14A—C15A2.3 (4)C12B—C13B—C14B—C15B1.0 (4)
C13A—C14A—C15A—C16A0.3 (4)C13B—C14B—C15B—C16B0.6 (4)
C13A—C14A—C15A—C18A179.1 (3)C13B—C14B—C15B—C18B179.0 (3)
C14A—C15A—C16A—C17A2.2 (4)C14B—C15B—C16B—C17B0.2 (4)
C18A—C15A—C16A—C17A178.4 (3)C18B—C15B—C16B—C17B179.8 (3)
C15A—C16A—C17A—C12A2.6 (4)C13B—C12B—C17B—C16B0.2 (4)
C13A—C12A—C17A—C16A0.6 (4)N4B—C12B—C17B—C16B177.2 (2)
N4A—C12A—C17A—C16A179.1 (2)C15B—C16B—C17B—C12B0.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8a—H8a···N1b0.932.833.502 (3)130
C8a—H8a···N2b0.932.893.502 (3)125
C5a—H5a···N1ai0.932.603.376 (3)141
C11a—H11a···N6aii0.932.963.715 (3)140
C18a—H18b···N1aiii0.962.873.432 (4)119
C5b—H5b···N1biv0.932.483.244 (3)140
C14b—H14b···πv0.933.053.951 (4)164
C18a—H18a···N2bvi0.962.693.623 (3)164
C11b—H11b···N6avii0.932.653.243 (3)122
C17b—H17b···N1aiv0.932.683.505 (4)148
Symmetry codes: (i) x, y+2, z+2; (ii) x, y+1, z+1; (iii) x, y1, z; (iv) x+1, y+2, z+2; (v) x+1, y+1, z+1; (vi) x1, y1, z; (vii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H12N4
Mr236.28
Crystal system, space groupTriclinic, 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)
V3)1204.5 (6)
Z4
Radiation typeCu Kα
µ (mm1)0.65
Crystal size (mm)0.42 × 0.28 × 0.20
Data collection
DiffractometerKM4 four-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5413, 5153, 1942
Rint0.039
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.164, 0.96
No. of reflections5153
No. of parameters328
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8a—H8a···N1b0.932.833.502 (3)130
C8a—H8a···N2b0.932.893.502 (3)125
C5a—H5a···N1ai0.932.603.376 (3)141
C11a—H11a···N6aii0.932.963.715 (3)140
C18a—H18b···N1aiii0.962.873.432 (4)119
C5b—H5b···N1biv0.932.483.244 (3)140
C14b—H14b···πv0.933.053.951 (4)164
C18a—H18a···N2bvi0.962.693.623 (3)164
C11b—H11b···N6avii0.932.653.243 (3)122
C17b—H17b···N1aiv0.932.683.505 (4)148
Symmetry codes: (i) x, y+2, z+2; (ii) x, y+1, z+1; (iii) x, y1, z; (iv) x+1, y+2, z+2; (v) x+1, y+1, z+1; (vi) x1, y1, z; (vii) x+1, y, z.
 

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