organic compounds
1,4-Bis(1H-1,2,4-triazol-1-yl)benzene
aInstitute of Molecular Science, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
*Correspondence e-mail: luliping@sxu.edu.cn
The complete molecule of the title compound, C10H8N6, is generated by crystallographic inversion symmetry; the dihedral angle between the planes of the benzene and triazole rings is 16.7 (2)°. In the crystal, inversion dimers linked by pairs of weak C—H⋯N hydrogen bonds generate R22(6) loops. Weak aromatic π–π stacking interactions [centroid–centroid separation = 3.809 (1) Å] are also observed.
Keywords: crystal structure; 1,4-bis(1H-1,2,4-triazol-1-yl)benzene; C—H⋯N hydrogen bonding; π–π interaction.
CCDC reference: 1533318
Structure description
Derivatives of 1,2,4-triazole exhibit a wide range of bioactivities, including anticancer activity, antitubercular activity and kinase inhibition (Kaur et al., 2016; Keri et al., 2015). Their copper complexes can inhibit the activity of protein tyrosine phosphatase (Lu & Zhu, 2014). Thus, we reacted 2,5-bis(1H-1,2,4-triazol-1-yl)terephthalic acid with CuCl2 under hydrothermal conditions in an attempt to form a complex, but instead crystals of the title compound, (I), were obtained.
The molecular structure of (I) is illustrated in Fig. 1. The consists of half a molecule; the complete molecule is generated by an inversion operation. The planes of the benzene and triazole rings are inclined at an angle of 16.7 (2)°. In the crystal, molecules are connected through weak C—H⋯N hydrogen bonds (Table 1) and π–π interactions [centroid–centroid separation = 3.809 (1) Å], leading to the formation of a supramolecular network (Fig. 2).
Synthesis and crystallization
A mixture containing CuCl2·4H2O (0.10 mmol, 17 mg), 2,5-bis(1H-1,2,4-triazol-1-yl)terephthalic acid (0.05 mmol, 15 mg), 1,10-phenanthroline (0.05 mmol, 8.5 mg), dimethylformamide (1.0 ml) and H2O (6.0 ml) was stirred for 30 min at room temperature. The reaction mixture was sealed in a Teflon-lined stainless steel vessel and then heated to 433 K for 3 d and then allowed to cool gradually to room temperature. Colourless blocks of the title compound were collected by filtration and washed with water.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1533318
https://doi.org/10.1107/S2414314617002723/hb4114sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002723/hb4114Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617002723/hb4114Isup3.cml
Data collection: APEX2 (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C10H8N6 | F(000) = 220 |
Mr = 212.22 | Dx = 1.514 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8091 (3) Å | Cell parameters from 2111 reflections |
b = 10.2616 (9) Å | θ = 3.4–27.5° |
c = 11.9768 (11) Å | µ = 0.10 mm−1 |
β = 96.165 (3)° | T = 298 K |
V = 465.44 (7) Å3 | Block, colorless |
Z = 2 | 0.20 × 0.20 × 0.20 mm |
Bruker APEXII CCD diffractometer | 875 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
φ and ω scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −3→4 |
Tmin = 0.669, Tmax = 0.746 | k = −13→13 |
4210 measured reflections | l = −15→15 |
1057 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0567P)2 + 0.1337P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
1057 reflections | Δρmax = 0.23 e Å−3 |
73 parameters | Δρmin = −0.17 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.8017 (3) | 0.48118 (10) | 0.21842 (9) | 0.0307 (3) | |
N2 | 0.7691 (4) | 0.58859 (12) | 0.28330 (10) | 0.0451 (4) | |
N3 | 0.6288 (4) | 0.40718 (13) | 0.37506 (11) | 0.0459 (4) | |
C1 | 0.6654 (5) | 0.53760 (15) | 0.37491 (13) | 0.0467 (4) | |
H1 | 0.620016 | 0.588563 | 0.435947 | 0.056* | |
C2 | 0.7160 (4) | 0.37557 (14) | 0.27543 (12) | 0.0417 (4) | |
H2 | 0.718064 | 0.290825 | 0.247992 | 0.050* | |
C3 | 0.9038 (3) | 0.49129 (12) | 0.10767 (11) | 0.0282 (3) | |
C4 | 0.8869 (4) | 0.61044 (13) | 0.05306 (11) | 0.0331 (3) | |
H4 | 0.811019 | 0.684228 | 0.088642 | 0.040* | |
C5 | 1.0163 (4) | 0.38103 (13) | 0.05481 (11) | 0.0341 (4) | |
H5 | 1.026722 | 0.301276 | 0.091893 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0397 (7) | 0.0278 (6) | 0.0257 (6) | −0.0006 (5) | 0.0082 (5) | −0.0003 (4) |
N2 | 0.0729 (9) | 0.0319 (7) | 0.0343 (7) | −0.0005 (6) | 0.0228 (6) | −0.0043 (5) |
N3 | 0.0651 (9) | 0.0412 (7) | 0.0346 (7) | −0.0032 (6) | 0.0199 (6) | 0.0029 (5) |
C1 | 0.0691 (11) | 0.0401 (8) | 0.0344 (8) | 0.0005 (7) | 0.0224 (7) | −0.0017 (6) |
C2 | 0.0623 (10) | 0.0307 (7) | 0.0342 (7) | −0.0038 (7) | 0.0153 (7) | 0.0024 (6) |
C3 | 0.0309 (7) | 0.0302 (7) | 0.0239 (6) | −0.0018 (5) | 0.0045 (5) | −0.0004 (5) |
C4 | 0.0439 (8) | 0.0260 (7) | 0.0306 (7) | 0.0025 (5) | 0.0099 (6) | −0.0025 (5) |
C5 | 0.0471 (8) | 0.0261 (6) | 0.0301 (7) | 0.0035 (6) | 0.0095 (6) | 0.0039 (5) |
N1—C2 | 1.3397 (17) | C2—H2 | 0.9300 |
N1—N2 | 1.3620 (15) | C3—C4 | 1.3848 (18) |
N1—C3 | 1.4255 (16) | C3—C5 | 1.3867 (18) |
N2—C1 | 1.3141 (19) | C4—C5i | 1.3839 (17) |
N3—C2 | 1.3133 (18) | C4—H4 | 0.9300 |
N3—C1 | 1.346 (2) | C5—H5 | 0.9300 |
C1—H1 | 0.9300 | ||
C2—N1—N2 | 108.77 (11) | N1—C2—H2 | 124.4 |
C2—N1—C3 | 129.70 (11) | C4—C3—C5 | 120.38 (12) |
N2—N1—C3 | 121.51 (10) | C4—C3—N1 | 120.02 (11) |
C1—N2—N1 | 102.01 (12) | C5—C3—N1 | 119.60 (11) |
C2—N3—C1 | 102.01 (12) | C5i—C4—C3 | 119.55 (12) |
N2—C1—N3 | 115.95 (13) | C5i—C4—H4 | 120.2 |
N2—C1—H1 | 122.0 | C3—C4—H4 | 120.2 |
N3—C1—H1 | 122.0 | C4i—C5—C3 | 120.07 (12) |
N3—C2—N1 | 111.26 (13) | C4i—C5—H5 | 120.0 |
N3—C2—H2 | 124.4 | C3—C5—H5 | 120.0 |
C2—N1—N2—C1 | 0.02 (17) | N2—N1—C3—C4 | −16.2 (2) |
C3—N1—N2—C1 | 178.56 (13) | C2—N1—C3—C5 | −17.3 (2) |
N1—N2—C1—N3 | 0.1 (2) | N2—N1—C3—C5 | 164.48 (13) |
C2—N3—C1—N2 | −0.2 (2) | C5—C3—C4—C5i | −0.1 (2) |
C1—N3—C2—N1 | 0.19 (19) | N1—C3—C4—C5i | −179.45 (12) |
N2—N1—C2—N3 | −0.14 (19) | C4—C3—C5—C4i | 0.1 (2) |
C3—N1—C2—N3 | −178.52 (13) | N1—C3—C5—C4i | 179.46 (13) |
C2—N1—C3—C4 | 162.05 (15) |
Symmetry code: (i) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N3ii | 0.93 | 2.55 | 3.3563 (19) | 146 |
C5—H5···N2iii | 0.93 | 2.71 | 3.6184 (18) | 165 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+2, y−1/2, −z+1/2. |
Funding information
Funding for this research was provided by: National Natural Science Foundation of Chinahttps://doi.org/10.13039/501100001809 (award No. 21571118).
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