metal-organic compounds
A new AgI complex based on 1-[(1H-benzimidazol-1-yl)methyl]-1H-1,2,4-triazole
aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and bDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China
*Correspondence e-mail: mxr@zzu.edu.cn
In the title complex, bis{μ-1-[(1H-benzimidazol-1-yl)methyl]-1H-1,2,4-triazole}disilver(I) dinitrate, [Ag2(C10H9N5)2](NO3)2, the AgI ion is nearly linearly coordinated [N—Ag—N angle is 155.72 (14)°] by two 1-[(1H-benzimidazole-1-yl)methyl]-1H-1,2,4-triazole (bmt) ligands. In addition, two bmt ligands link two AgI ions, forming a dinuclear unit with an Ag⋯Ag distance of 5.0179 (15) Å. The whole complex is generated by an inversion centre. The dinuclear units and the NO3− counter-ions are connected by N—H⋯O hydrogen bonds and weak Ag⋯O interactions [2.831 (5), 2.887 (5) and 2.908 (5) Å], leading to a three-dimensional structure.
Related literature
For background to complexes based on benzimidazole or triazole and their derivatives, see: Yang et al. (2010); Li et al. (2010); Tian et al. (2011); Zhang et al. (2011).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrystalClear (Rigaku/MSC, 2006); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536811048501/vm2136sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048501/vm2136Isup2.hkl
The ligand 1-[(1H-benzimidazole-1-yl)methyl]-1H-1,2,4-triazole (0.1 mmol) in methanol (4 ml) was added dropwise to an aqueous solution (3 ml) of AgNO3 (0.1 mmol). The resulting solution was allowed to stand at room temperature in the dark. After four weeks good quality colorless crystals were obtained from the filtrate and dried in air.
H atoms are positioned geometrically and refined as riding atoms, with C-H = 0.93 (aromatic) and 0.97 (CH2) Å and N-H = 0.86 Å and with Uiso(H) = 1.2 Ueq(C,N).
Many complexes based on benzimidazole or triazole and their derivatives have been synthesized and characterized owing to the strong coordination abilities of these multidentate N-heterocyclic ligands and the interesting properties and potential applications of these complexes (Yang et al., 2010; Li et al., 2010; Tian et al., 2011; Zhang et al., 2011). We are engaged in the synthesis of unsymmetrical N-heterocyclic ligands and have synthesized the compound 1-[(1H-benzimidazole-1-yl)methyl]-1H-1,2,4-triazole (bmt). In this work, we selected this compound as ligand and generated a new complex [Ag2(C10H9N5)2](NO3)2, (I), which is reported here.
In complex (I) each AgI ion is two-coordinated by two N atom from one triazole group and one benzimidazole group of two different 1-[(1H-benzimidazole-1-yl)methyl]-1H-1,2,4-triazole ligands and the nitrate anion does not coordinate to the AgI ion (Fig. 1). Two bmt ligands bridge two AgI ions leading to a dinuclear unit [Ag2(C10H9N5)2] with Ag1—Ag1i distance of 5.0179 (15) Å (symmetry code: (i) -x-1, -y+2, -z). [Ag2(C10H9N5)2] units and NO3- groups are linked through weak Ag···O interactions and N—H···O hydrogen bonds (Table 1) resulting in a three-dimensional packing in solid state.
For background to complexes based on benzimidazole or triazole and their derivatives, see: Yang et al. (2010); Li et al. (2010); Tian et al. (2011); Zhang et al. (2011).
Data collection: CrystalClear (Rigaku/MSC, 2006); cell
CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. View of the title complex showing labeling and 30% probability displacement ellipsoids. Hydrogen bonds are indicated by dashed lines. Symmetry code: (i) -x - 1, -y + 2, -z. |
[Ag2(C10H9N5)2](NO3)2 | F(000) = 728 |
Mr = 738.20 | Dx = 2.057 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3140 reflections |
a = 9.4947 (19) Å | θ = 2.4–27.9° |
b = 13.569 (3) Å | µ = 1.71 mm−1 |
c = 10.174 (2) Å | T = 293 K |
β = 114.56 (3)° | Prism, colourless |
V = 1192.1 (4) Å3 | 0.19 × 0.17 × 0.14 mm |
Z = 2 |
Rigaku Saturn diffractometer | 2158 independent reflections |
Radiation source: fine-focus sealed tube | 1952 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 25.3°, θmin = 2.4° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006) | k = −16→16 |
Tmin = 0.737, Tmax = 0.796 | l = −12→11 |
9572 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0419P)2 + 1.7006P] where P = (Fo2 + 2Fc2)/3 |
2158 reflections | (Δ/σ)max = 0.001 |
181 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
[Ag2(C10H9N5)2](NO3)2 | V = 1192.1 (4) Å3 |
Mr = 738.20 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.4947 (19) Å | µ = 1.71 mm−1 |
b = 13.569 (3) Å | T = 293 K |
c = 10.174 (2) Å | 0.19 × 0.17 × 0.14 mm |
β = 114.56 (3)° |
Rigaku Saturn diffractometer | 2158 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006) | 1952 reflections with I > 2σ(I) |
Tmin = 0.737, Tmax = 0.796 | Rint = 0.034 |
9572 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.70 e Å−3 |
2158 reflections | Δρmin = −0.28 e Å−3 |
181 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 | ||
Ag1 | −0.34103 (4) | 0.89095 (3) | 0.20814 (4) | 0.04938 (17) | |
N1 | −0.0927 (4) | 0.9097 (2) | 0.3164 (4) | 0.0326 (8) | |
N2 | 0.1479 (4) | 0.9666 (3) | 0.3996 (4) | 0.0354 (8) | |
H2B | 0.2248 | 1.0035 | 0.4080 | 0.043* | |
N3 | −0.1878 (4) | 1.0476 (2) | 0.0747 (4) | 0.0320 (8) | |
N4 | −0.1943 (5) | 0.9813 (3) | −0.0280 (4) | 0.0449 (10) | |
N5 | −0.4205 (4) | 1.0613 (3) | −0.0931 (4) | 0.0374 (8) | |
N6 | 0.3779 (5) | 1.1840 (3) | 0.4722 (5) | 0.0470 (10) | |
O1 | 0.3112 (6) | 1.1880 (4) | 0.3398 (4) | 0.0877 (14) | |
O2 | 0.3944 (6) | 1.1033 (3) | 0.5326 (5) | 0.0818 (14) | |
O3 | 0.4245 (5) | 1.2605 (3) | 0.5397 (5) | 0.0801 (13) | |
C1 | 0.0033 (5) | 0.8484 (3) | 0.4281 (4) | 0.0320 (9) | |
C2 | −0.0334 (6) | 0.7641 (3) | 0.4866 (5) | 0.0387 (10) | |
H2A | −0.1339 | 0.7396 | 0.4515 | 0.046* | |
C3 | 0.0871 (6) | 0.7193 (3) | 0.5989 (5) | 0.0446 (12) | |
H3A | 0.0670 | 0.6633 | 0.6409 | 0.054* | |
C4 | 0.2383 (6) | 0.7552 (3) | 0.6518 (5) | 0.0454 (12) | |
H4A | 0.3158 | 0.7223 | 0.7277 | 0.055* | |
C5 | 0.2760 (5) | 0.8380 (3) | 0.5946 (5) | 0.0415 (11) | |
H5A | 0.3769 | 0.8618 | 0.6295 | 0.050* | |
C6 | 0.1542 (5) | 0.8840 (3) | 0.4813 (5) | 0.0345 (10) | |
C7 | −0.0011 (5) | 0.9789 (3) | 0.3042 (4) | 0.0306 (9) | |
C8 | −0.0451 (5) | 1.0643 (3) | 0.2027 (4) | 0.0352 (10) | |
H8A | −0.0574 | 1.1222 | 0.2528 | 0.042* | |
H8B | 0.0379 | 1.0774 | 0.1732 | 0.042* | |
C9 | −0.3227 (5) | 1.0931 (3) | 0.0341 (5) | 0.0353 (10) | |
H9A | −0.3452 | 1.1409 | 0.0881 | 0.042* | |
C10 | −0.3371 (6) | 0.9929 (4) | −0.1265 (5) | 0.0450 (11) | |
H10A | −0.3772 | 0.9569 | −0.2120 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0295 (2) | 0.0625 (3) | 0.0471 (3) | 0.00013 (17) | 0.00685 (17) | 0.00857 (18) |
N1 | 0.0290 (19) | 0.0329 (19) | 0.0328 (19) | 0.0005 (16) | 0.0098 (16) | −0.0039 (15) |
N2 | 0.030 (2) | 0.038 (2) | 0.036 (2) | −0.0027 (16) | 0.0114 (16) | −0.0009 (16) |
N3 | 0.0292 (19) | 0.0302 (17) | 0.0335 (19) | 0.0019 (15) | 0.0100 (16) | 0.0020 (15) |
N4 | 0.040 (2) | 0.046 (2) | 0.047 (2) | 0.0002 (19) | 0.016 (2) | −0.0166 (19) |
N5 | 0.030 (2) | 0.041 (2) | 0.036 (2) | 0.0014 (17) | 0.0097 (17) | 0.0027 (17) |
N6 | 0.036 (2) | 0.056 (3) | 0.047 (3) | −0.007 (2) | 0.015 (2) | −0.004 (2) |
O1 | 0.103 (4) | 0.097 (3) | 0.048 (2) | 0.023 (3) | 0.016 (2) | −0.003 (2) |
O2 | 0.089 (3) | 0.060 (3) | 0.088 (3) | −0.008 (2) | 0.029 (3) | 0.028 (2) |
O3 | 0.067 (3) | 0.064 (3) | 0.094 (3) | −0.025 (2) | 0.019 (2) | −0.029 (2) |
C1 | 0.033 (2) | 0.032 (2) | 0.028 (2) | 0.0053 (18) | 0.0098 (18) | −0.0064 (18) |
C2 | 0.040 (3) | 0.034 (2) | 0.040 (2) | 0.000 (2) | 0.014 (2) | −0.0028 (19) |
C3 | 0.060 (3) | 0.033 (2) | 0.037 (3) | 0.004 (2) | 0.018 (2) | 0.000 (2) |
C4 | 0.055 (3) | 0.041 (3) | 0.034 (2) | 0.018 (2) | 0.012 (2) | 0.001 (2) |
C5 | 0.034 (3) | 0.049 (3) | 0.035 (2) | 0.005 (2) | 0.008 (2) | −0.007 (2) |
C6 | 0.036 (3) | 0.035 (2) | 0.031 (2) | 0.0020 (19) | 0.013 (2) | −0.0054 (18) |
C7 | 0.030 (2) | 0.031 (2) | 0.028 (2) | −0.0005 (18) | 0.0106 (18) | −0.0052 (17) |
C8 | 0.031 (2) | 0.034 (2) | 0.036 (2) | −0.0011 (19) | 0.0093 (19) | −0.0042 (19) |
C9 | 0.037 (3) | 0.037 (2) | 0.032 (2) | 0.003 (2) | 0.015 (2) | 0.0031 (19) |
C10 | 0.040 (3) | 0.049 (3) | 0.043 (3) | −0.007 (2) | 0.014 (2) | −0.010 (2) |
Ag1—N1 | 2.163 (4) | N6—O2 | 1.233 (5) |
Ag1—N5i | 2.171 (4) | C1—C6 | 1.390 (6) |
N1—C7 | 1.321 (5) | C1—C2 | 1.399 (6) |
N1—C1 | 1.397 (5) | C2—C3 | 1.377 (6) |
N2—C7 | 1.353 (5) | C2—H2A | 0.9300 |
N2—C6 | 1.382 (5) | C3—C4 | 1.395 (7) |
N2—H2B | 0.8600 | C3—H3A | 0.9300 |
N3—C9 | 1.325 (5) | C4—C5 | 1.380 (7) |
N3—N4 | 1.361 (5) | C4—H4A | 0.9300 |
N3—C8 | 1.454 (5) | C5—C6 | 1.396 (6) |
N4—C10 | 1.318 (6) | C5—H5A | 0.9300 |
N5—C9 | 1.313 (6) | C7—C8 | 1.492 (6) |
N5—C10 | 1.352 (6) | C8—H8A | 0.9700 |
N5—Ag1i | 2.171 (4) | C8—H8B | 0.9700 |
N6—O3 | 1.222 (5) | C9—H9A | 0.9300 |
N6—O1 | 1.229 (5) | C10—H10A | 0.9300 |
N1—Ag1—N5i | 155.72 (14) | C4—C3—H3A | 118.9 |
C7—N1—C1 | 105.5 (4) | C5—C4—C3 | 121.9 (4) |
C7—N1—Ag1 | 131.1 (3) | C5—C4—H4A | 119.1 |
C1—N1—Ag1 | 123.3 (3) | C3—C4—H4A | 119.1 |
C7—N2—C6 | 107.6 (4) | C4—C5—C6 | 116.2 (4) |
C7—N2—H2B | 126.2 | C4—C5—H5A | 121.9 |
C6—N2—H2B | 126.2 | C6—C5—H5A | 121.9 |
C9—N3—N4 | 109.8 (4) | N2—C6—C1 | 105.5 (4) |
C9—N3—C8 | 128.8 (4) | N2—C6—C5 | 132.3 (4) |
N4—N3—C8 | 121.2 (3) | C1—C6—C5 | 122.2 (4) |
C10—N4—N3 | 102.1 (4) | N1—C7—N2 | 112.2 (4) |
C9—N5—C10 | 103.0 (4) | N1—C7—C8 | 127.7 (4) |
C9—N5—Ag1i | 125.8 (3) | N2—C7—C8 | 120.1 (4) |
C10—N5—Ag1i | 131.1 (3) | N3—C8—C7 | 112.8 (3) |
O3—N6—O1 | 118.6 (5) | N3—C8—H8A | 109.0 |
O3—N6—O2 | 122.2 (5) | C7—C8—H8A | 109.0 |
O1—N6—O2 | 119.1 (5) | N3—C8—H8B | 109.0 |
C6—C1—N1 | 109.2 (4) | C7—C8—H8B | 109.0 |
C6—C1—C2 | 121.1 (4) | H8A—C8—H8B | 107.8 |
N1—C1—C2 | 129.7 (4) | N5—C9—N3 | 110.5 (4) |
C3—C2—C1 | 116.5 (4) | N5—C9—H9A | 124.8 |
C3—C2—H2A | 121.8 | N3—C9—H9A | 124.8 |
C1—C2—H2A | 121.8 | N4—C10—N5 | 114.6 (4) |
C2—C3—C4 | 122.2 (4) | N4—C10—H10A | 122.7 |
C2—C3—H3A | 118.9 | N5—C10—H10A | 122.7 |
N5i—Ag1—N1—C7 | −24.9 (5) | C4—C5—C6—N2 | 179.8 (4) |
N5i—Ag1—N1—C1 | 149.8 (3) | C4—C5—C6—C1 | −0.4 (6) |
C9—N3—N4—C10 | 0.5 (5) | C1—N1—C7—N2 | 0.3 (4) |
C8—N3—N4—C10 | −176.4 (4) | Ag1—N1—C7—N2 | 175.7 (3) |
C7—N1—C1—C6 | 0.1 (4) | C1—N1—C7—C8 | −178.8 (4) |
Ag1—N1—C1—C6 | −175.7 (3) | Ag1—N1—C7—C8 | −3.3 (6) |
C7—N1—C1—C2 | 179.6 (4) | C6—N2—C7—N1 | −0.7 (5) |
Ag1—N1—C1—C2 | 3.7 (6) | C6—N2—C7—C8 | 178.5 (3) |
C6—C1—C2—C3 | 0.2 (6) | C9—N3—C8—C7 | 114.0 (5) |
N1—C1—C2—C3 | −179.2 (4) | N4—N3—C8—C7 | −69.8 (5) |
C1—C2—C3—C4 | −0.4 (6) | N1—C7—C8—N3 | −23.6 (6) |
C2—C3—C4—C5 | 0.1 (7) | N2—C7—C8—N3 | 157.4 (4) |
C3—C4—C5—C6 | 0.3 (6) | C10—N5—C9—N3 | 0.7 (5) |
C7—N2—C6—C1 | 0.7 (4) | Ag1i—N5—C9—N3 | 178.7 (3) |
C7—N2—C6—C5 | −179.5 (4) | N4—N3—C9—N5 | −0.8 (5) |
N1—C1—C6—N2 | −0.5 (4) | C8—N3—C9—N5 | 175.8 (4) |
C2—C1—C6—N2 | 180.0 (4) | N3—N4—C10—N5 | 0.0 (5) |
N1—C1—C6—C5 | 179.6 (4) | C9—N5—C10—N4 | −0.4 (5) |
C2—C1—C6—C5 | 0.1 (6) | Ag1i—N5—C10—N4 | −178.3 (3) |
Symmetry code: (i) −x−1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C10H9N5)2](NO3)2 |
Mr | 738.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.4947 (19), 13.569 (3), 10.174 (2) |
β (°) | 114.56 (3) |
V (Å3) | 1192.1 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.71 |
Crystal size (mm) | 0.19 × 0.17 × 0.14 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2006) |
Tmin, Tmax | 0.737, 0.796 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9572, 2158, 1952 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.095, 1.09 |
No. of reflections | 2158 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.28 |
Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The authors thank the Science and Technology Department of Henan Province (082102330003).
References
Li, Y., Yang, H., Ding, Y. & Meng, X. (2010). Acta Cryst. E66, m1155. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2006). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, L., Yan, L. & Liu, S. Y. (2011). J. Coord. Chem. 64, 2945–2952. Web of Science CSD CrossRef CAS Google Scholar
Yang, H.-X., Zhang, J., Ding, Y.-N. & Meng, X.-R. (2010). Acta Cryst. E66, m578. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, P., Li, D. S., Zhao, J., Wu, Y. P., Li, C., Zou, K. & Lu, J. Y. (2011). J. Coord. Chem. 64, 2329–2341. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Many complexes based on benzimidazole or triazole and their derivatives have been synthesized and characterized owing to the strong coordination abilities of these multidentate N-heterocyclic ligands and the interesting properties and potential applications of these complexes (Yang et al., 2010; Li et al., 2010; Tian et al., 2011; Zhang et al., 2011). We are engaged in the synthesis of unsymmetrical N-heterocyclic ligands and have synthesized the compound 1-[(1H-benzimidazole-1-yl)methyl]-1H-1,2,4-triazole (bmt). In this work, we selected this compound as ligand and generated a new complex [Ag2(C10H9N5)2](NO3)2, (I), which is reported here.
In complex (I) each AgI ion is two-coordinated by two N atom from one triazole group and one benzimidazole group of two different 1-[(1H-benzimidazole-1-yl)methyl]-1H-1,2,4-triazole ligands and the nitrate anion does not coordinate to the AgI ion (Fig. 1). Two bmt ligands bridge two AgI ions leading to a dinuclear unit [Ag2(C10H9N5)2] with Ag1—Ag1i distance of 5.0179 (15) Å (symmetry code: (i) -x-1, -y+2, -z). [Ag2(C10H9N5)2] units and NO3- groups are linked through weak Ag···O interactions and N—H···O hydrogen bonds (Table 1) resulting in a three-dimensional packing in solid state.