Acta Cryst. (2013). E69, m148 [ doi:10.1107/S1600536813003711 ]
The asymmetric unit of the title salt, (C8H10N3)[FeCl4], contains one 1,3-dimethyl-1H-1,2,3-benzotriazol-3-ium cation and one tetrachloridoferrate anion. The FeIII atom in the anion is tetrahedrally coordinated by four Cl atoms. In the crystal, interactions are observed between the Cl atoms and the triazolium ring [Cl
centroid distances = 3.587 (3) and 3.866 (3) Å].
FeCl3.6H2O (0.1 mmol, 27.0 mg) was dissolved in 15 ml CH3OH. To this yellow solution, one equivalent of 1,3-dimethyl-1H-benzo[1,2,3]triazolenium chlorate (0.1 mmol, 18.4 mg) was added with stirring. The mixture was filtered and held at room temperature to allow slow evaporation of solvent after stirring 30 min. Block crystals suitable for X-ray diffraction were obtained after one week (yield: 64%).
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (CH) and 0.96 Å (CH3), and with Uiso(H) = 1.5Ueq(C) for methyl groups or 1.2Ueq(C) otherwise.
Data collection: CrysAlis PRO (Oxford Diffraction, 2012); cell refinement: CrysAlis PRO (Oxford Diffraction, 2012); data reduction: CrysAlis PRO (Oxford Diffraction, 2012); 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).
![[Figure 1]](./hy2615fig1thm.gif)
| Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./hy2615fig2thm.gif)
| Fig. 2. Crystal packing of the title compound viewed along the a axis. |
| (C8H10N3)[FeCl4] | F(000) = 1384 |
| Mr = 345.84 | Dx = 1.575 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 1751 reflections |
| a = 10.2920 (5) Å | θ = 3.1–28.5° |
| b = 12.5518 (6) Å | µ = 1.74 mm−1 |
| c = 22.5857 (9) Å | T = 293 K |
| V = 2917.7 (2) Å3 | Block, yellow |
| Z = 8 | 0.32 × 0.28 × 0.25 mm |
| Oxford Diffraction SuperNova (Dual, Cu at zero, Eos) diffractometer | 3016 independent reflections |
| Radiation source: fine-focus sealed tube | 1828 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.031 |
| Detector resolution: 16.0733 pixels mm-1 | θmax = 26.5°, θmin = 3.1° |
| ω scans | h = −12→6 |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2012) | k = −15→12 |
| Tmin = 0.578, Tmax = 0.647 | l = −28→28 |
| 8114 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.183 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0779P)2 + 1.072P] where P = (Fo2 + 2Fc2)/3 |
| 3016 reflections | (Δ/σ)max < 0.001 |
| 147 parameters | Δρmax = 0.53 e Å−3 |
| 0 restraints | Δρmin = −0.39 e Å−3 |
| (C8H10N3)[FeCl4] | V = 2917.7 (2) Å3 |
| Mr = 345.84 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 10.2920 (5) Å | µ = 1.74 mm−1 |
| b = 12.5518 (6) Å | T = 293 K |
| c = 22.5857 (9) Å | 0.32 × 0.28 × 0.25 mm |
| Oxford Diffraction SuperNova (Dual, Cu at zero, Eos) diffractometer | 3016 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2012) | 1828 reflections with I > 2σ(I) |
| Tmin = 0.578, Tmax = 0.647 | Rint = 0.031 |
| 8114 measured reflections | θmax = 26.5° |
| R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
| wR(F2) = 0.183 | Δρmax = 0.53 e Å−3 |
| S = 1.05 | Δρmin = −0.39 e Å−3 |
| 3016 reflections | Absolute structure: ? |
| 147 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
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 | ||
| N1 | 0.2130 (5) | 0.5085 (4) | 0.3377 (2) | 0.0934 (14) | |
| N2 | 0.1550 (5) | 0.5572 (4) | 0.3863 (2) | 0.0907 (14) | |
| N3 | 0.2259 (5) | 0.5203 (4) | 0.4309 (2) | 0.0912 (13) | |
| C1 | 0.3237 (4) | 0.4541 (4) | 0.4130 (2) | 0.0650 (11) | |
| C2 | 0.4177 (6) | 0.3997 (5) | 0.4452 (2) | 0.0927 (17) | |
| H2 | 0.4238 | 0.4034 | 0.4863 | 0.111* | |
| C3 | 0.5016 (6) | 0.3393 (5) | 0.4106 (3) | 0.0986 (17) | |
| H3 | 0.5669 | 0.3006 | 0.4293 | 0.118* | |
| C4 | 0.4922 (6) | 0.3345 (6) | 0.3510 (3) | 0.1023 (18) | |
| H4 | 0.5522 | 0.2937 | 0.3302 | 0.123* | |
| C5 | 0.3950 (6) | 0.3889 (5) | 0.3193 (2) | 0.0877 (16) | |
| H5 | 0.3874 | 0.3845 | 0.2783 | 0.105* | |
| C6 | 0.3140 (6) | 0.4478 (5) | 0.3524 (2) | 0.0823 (15) | |
| C7 | 0.1582 (6) | 0.5291 (6) | 0.2780 (3) | 0.124 (3) | |
| H7A | 0.1317 | 0.4630 | 0.2604 | 0.186* | |
| H7B | 0.2230 | 0.5622 | 0.2535 | 0.186* | |
| H7C | 0.0844 | 0.5755 | 0.2814 | 0.186* | |
| C8 | 0.1916 (6) | 0.5507 (5) | 0.4913 (2) | 0.111 (2) | |
| H8A | 0.1229 | 0.6023 | 0.4903 | 0.166* | |
| H8B | 0.2662 | 0.5808 | 0.5106 | 0.166* | |
| H8C | 0.1632 | 0.4888 | 0.5127 | 0.166* | |
| Fe1 | 0.53140 (7) | 0.75129 (5) | 0.36820 (3) | 0.0621 (3) | |
| Cl1 | 0.40700 (15) | 0.76662 (12) | 0.44622 (6) | 0.0934 (5) | |
| Cl2 | 0.6707 (2) | 0.62448 (18) | 0.38165 (8) | 0.1478 (9) | |
| Cl3 | 0.63300 (15) | 0.90130 (13) | 0.35368 (7) | 0.0997 (5) | |
| Cl4 | 0.40818 (16) | 0.71994 (13) | 0.29142 (6) | 0.1007 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.089 (3) | 0.084 (3) | 0.108 (4) | −0.025 (3) | −0.029 (3) | 0.027 (3) |
| N2 | 0.086 (3) | 0.079 (3) | 0.107 (4) | −0.005 (3) | −0.020 (3) | 0.016 (3) |
| N3 | 0.094 (3) | 0.083 (3) | 0.097 (3) | −0.019 (3) | 0.010 (3) | −0.012 (3) |
| C1 | 0.064 (3) | 0.070 (3) | 0.060 (3) | −0.009 (2) | 0.001 (2) | 0.004 (2) |
| C2 | 0.105 (4) | 0.108 (4) | 0.064 (3) | −0.027 (4) | −0.012 (3) | 0.008 (3) |
| C3 | 0.100 (4) | 0.116 (5) | 0.080 (4) | 0.019 (4) | −0.001 (3) | 0.007 (4) |
| C4 | 0.097 (4) | 0.127 (5) | 0.083 (4) | 0.001 (4) | 0.002 (3) | −0.012 (4) |
| C5 | 0.105 (4) | 0.108 (4) | 0.050 (3) | −0.030 (3) | 0.009 (3) | −0.009 (3) |
| C6 | 0.089 (4) | 0.087 (4) | 0.071 (3) | −0.036 (3) | −0.003 (3) | 0.003 (3) |
| C7 | 0.127 (5) | 0.136 (6) | 0.110 (5) | −0.039 (4) | −0.062 (4) | 0.046 (4) |
| C8 | 0.130 (5) | 0.109 (5) | 0.093 (4) | −0.037 (4) | 0.042 (4) | −0.043 (4) |
| Fe1 | 0.0725 (5) | 0.0589 (5) | 0.0548 (4) | 0.0043 (3) | 0.0006 (3) | 0.0041 (3) |
| Cl1 | 0.1005 (10) | 0.1047 (11) | 0.0749 (9) | 0.0156 (8) | 0.0246 (8) | 0.0135 (7) |
| Cl2 | 0.1852 (19) | 0.1443 (18) | 0.1138 (14) | 0.1036 (16) | 0.0155 (12) | 0.0183 (11) |
| Cl3 | 0.1123 (11) | 0.1022 (11) | 0.0847 (10) | −0.0438 (9) | −0.0079 (8) | 0.0060 (8) |
| Cl4 | 0.1173 (11) | 0.1100 (11) | 0.0748 (9) | −0.0393 (9) | −0.0193 (8) | 0.0016 (8) |
| N1—C6 | 1.332 (7) | C4—H4 | 0.9300 |
| N1—N2 | 1.390 (7) | C5—C6 | 1.342 (7) |
| N1—C7 | 1.485 (7) | C5—H5 | 0.9300 |
| N2—N3 | 1.327 (6) | C7—H7A | 0.9600 |
| N3—C1 | 1.367 (6) | C7—H7B | 0.9600 |
| N3—C8 | 1.460 (6) | C7—H7C | 0.9600 |
| C1—C6 | 1.373 (7) | C8—H8A | 0.9600 |
| C1—C2 | 1.390 (7) | C8—H8B | 0.9600 |
| C2—C3 | 1.390 (8) | C8—H8C | 0.9600 |
| C2—H2 | 0.9300 | Fe1—Cl2 | 2.1636 (17) |
| C3—C4 | 1.351 (8) | Fe1—Cl3 | 2.1786 (15) |
| C3—H3 | 0.9300 | Fe1—Cl4 | 2.1840 (14) |
| C4—C5 | 1.408 (8) | Fe1—Cl1 | 2.1867 (15) |
| C6—N1—N2 | 112.9 (5) | N1—C6—C5 | 131.3 (6) |
| C6—N1—C7 | 128.6 (6) | N1—C6—C1 | 105.8 (5) |
| N2—N1—C7 | 118.5 (5) | C5—C6—C1 | 122.9 (6) |
| N3—N2—N1 | 102.2 (4) | N1—C7—H7A | 109.5 |
| N2—N3—C1 | 113.1 (5) | N1—C7—H7B | 109.5 |
| N2—N3—C8 | 119.1 (5) | H7A—C7—H7B | 109.5 |
| C1—N3—C8 | 127.9 (5) | N1—C7—H7C | 109.5 |
| N3—C1—C6 | 106.1 (5) | H7A—C7—H7C | 109.5 |
| N3—C1—C2 | 131.0 (5) | H7B—C7—H7C | 109.5 |
| C6—C1—C2 | 122.9 (5) | N3—C8—H8A | 109.5 |
| C3—C2—C1 | 113.9 (5) | N3—C8—H8B | 109.5 |
| C3—C2—H2 | 123.0 | H8A—C8—H8B | 109.5 |
| C1—C2—H2 | 123.0 | N3—C8—H8C | 109.5 |
| C4—C3—C2 | 122.7 (5) | H8A—C8—H8C | 109.5 |
| C4—C3—H3 | 118.6 | H8B—C8—H8C | 109.5 |
| C2—C3—H3 | 118.6 | Cl2—Fe1—Cl3 | 109.81 (10) |
| C3—C4—C5 | 122.4 (6) | Cl2—Fe1—Cl4 | 111.32 (8) |
| C3—C4—H4 | 118.8 | Cl3—Fe1—Cl4 | 108.36 (6) |
| C5—C4—H4 | 118.8 | Cl2—Fe1—Cl1 | 109.85 (7) |
| C6—C5—C4 | 115.1 (5) | Cl3—Fe1—Cl1 | 109.04 (7) |
| C6—C5—H5 | 122.4 | Cl4—Fe1—Cl1 | 108.41 (7) |
| C4—C5—H5 | 122.4 | ||
| C6—N1—N2—N3 | −1.1 (5) | C3—C4—C5—C6 | 1.3 (8) |
| C7—N1—N2—N3 | 179.0 (4) | N2—N1—C6—C5 | −179.6 (5) |
| N1—N2—N3—C1 | 0.9 (5) | C7—N1—C6—C5 | 0.4 (9) |
| N1—N2—N3—C8 | −177.7 (4) | N2—N1—C6—C1 | 0.9 (5) |
| N2—N3—C1—C6 | −0.4 (5) | C7—N1—C6—C1 | −179.2 (5) |
| C8—N3—C1—C6 | 178.0 (5) | C4—C5—C6—N1 | 180.0 (5) |
| N2—N3—C1—C2 | −179.8 (5) | C4—C5—C6—C1 | −0.6 (7) |
| C8—N3—C1—C2 | −1.4 (8) | N3—C1—C6—N1 | −0.3 (5) |
| N3—C1—C2—C3 | 180.0 (5) | C2—C1—C6—N1 | 179.2 (5) |
| C6—C1—C2—C3 | 0.7 (7) | N3—C1—C6—C5 | −179.9 (5) |
| C1—C2—C3—C4 | 0.1 (8) | C2—C1—C6—C5 | −0.4 (7) |
| C2—C3—C4—C5 | −1.1 (9) |
We are thankful for support of this study by the National Natural Science Foundation of China (grant No. J0730425) and the Gansu Provincial Natural Science Foundation of China (grant No. 0710RJZA113).
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Iron-containing compounds are ubiquitous throughout the field of coordination chemistry. Recently, a variety of iron compounds have been added to the list of iron coordination complexes (Hay et al., 2003; Liu et al., 2000; Lorenz et al., 2000; Shapley et al., 2003).
In the title compound (Fig. 1), the FeIII atom in the [FeCl4]- anion is four-coordinated in a distorted tetrahedral geometry. The Cl—Fe—Cl bond angles are in the range of 108.35 (6)–111.33 (8) °, while the Fe—Cl bond lengths are in the range of 2.1634 (17)–2.1867 (14) Å. Three Cl—Fe—Cl angles are smaller than tetrahedral and the other three are greater than tetrahedral one. In the crystal, interactions between the Cl atoms and the triazolium rings are present [Cl···centroid distances = 3.587 (3) and 3.866 (3) Å].