Acta Cryst. (2012). E68, o214 [ doi:10.1107/S1600536811054328 ]
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2N,C1}telluriumThe crystal structure of the title compound, C9H12ClNTe, contains isolated molecules with no close Te
Cl intermolecular contacts and has the same composition as a previously published structure [Engman et al. (2004). Phosphorus Sulfur Silicon Relat. Elem. 179, 285-292]. However, in this case, the compound has crystallized in a centrosymmetric space group, unlike the previously published structure which contained enantiomerically pure chiral molecules. In all other aspects, the metrical parameters are similar. The molecules with a T-shaped coordination environment about the Te atom are linked into dimers by C-HCl interactions.
A stirred solution of bis[2-(dimethylaminomethyl)phenyl]ditelluride (Kaur et al., 1995) (0.5 g, 0.94 mmol) in diethylether (10 ml) was treated with HCl (3 ml in 20 ml distilled water). The reaction mixture was further stirred for 10 min. The resulting reaction mixture was evaporated to one third of its original volume and ethanol (5 ml) was added to get a yellow solid. It was redissolved in ethanol and stored in the refrigerator to get yellow needles of X-ray quality crystals. Yield 0.2 g, 35% mp 121°C (lit value 121°C). Anal. Calcd for C9H12ClTe: C, 36.37; H, 4.07; N, 4.37. Found C, 36.44; H, 4.04; N, 4.66.
H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.95 - 0.97 Å [Uiso(H) = 1.2Ueq(CH, CH2) [Uiso(H) = 1.5Ueq(CH3)].
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./pk2376fig1thm.gif)
| Fig. 1. Diagram of the contents of the asymmetric unit of C9H12ClNTe. Atomic displacement ellipsoids are drawn at the 30% level. |
![[Figure 2]](./pk2376fig2thm.gif)
| Fig. 2. The molecular packing for C9H12ClNTe viewed down the c axis. C—H···Cl secondary interactions are shown by dashed lines. |
| C9H12ClNTe | F(000) = 568 |
| Mr = 297.25 | Dx = 1.836 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 3931 reflections |
| a = 6.4514 (6) Å | θ = 5.1–32.6° |
| b = 7.0287 (7) Å | µ = 2.96 mm−1 |
| c = 23.847 (2) Å | T = 295 K |
| β = 95.967 (9)° | Irregular plate, pale yellow |
| V = 1075.49 (17) Å3 | 0.45 × 0.36 × 0.12 mm |
| Z = 4 |
| Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 3587 independent reflections |
| Radiation source: fine-focus sealed tube | 2998 reflections with I > 2σ(I) |
| graphite | Rint = 0.023 |
| Detector resolution: 10.5081 pixels mm-1 | θmax = 32.7°, θmin = 5.1° |
| ω scans | h = −9→9 |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007) | k = −6→10 |
| Tmin = 0.504, Tmax = 1.000 | l = −35→34 |
| 7778 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) = 0.096 | H-atom parameters constrained |
| S = 1.20 | w = 1/[σ2(Fo2) + (0.0327P)2 + 1.2847P] where P = (Fo2 + 2Fc2)/3 |
| 3587 reflections | (Δ/σ)max = 0.001 |
| 111 parameters | Δρmax = 2.25 e Å−3 |
| 0 restraints | Δρmin = −0.98 e Å−3 |
| C9H12ClNTe | V = 1075.49 (17) Å3 |
| Mr = 297.25 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 6.4514 (6) Å | µ = 2.96 mm−1 |
| b = 7.0287 (7) Å | T = 295 K |
| c = 23.847 (2) Å | 0.45 × 0.36 × 0.12 mm |
| β = 95.967 (9)° |
| Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 3587 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007) | 2998 reflections with I > 2σ(I) |
| Tmin = 0.504, Tmax = 1.000 | Rint = 0.023 |
| 7778 measured reflections | θmax = 32.7° |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.096 | Δρmax = 2.25 e Å−3 |
| S = 1.20 | Δρmin = −0.98 e Å−3 |
| 3587 reflections | Absolute structure: ? |
| 111 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| Te | 0.58681 (4) | 0.01772 (4) | 0.423777 (10) | 0.03896 (9) | |
| Cl | 0.29601 (17) | −0.23269 (17) | 0.41307 (5) | 0.0537 (3) | |
| N | 0.8374 (5) | 0.2560 (4) | 0.41417 (13) | 0.0372 (6) | |
| C1 | 0.5512 (6) | 0.0787 (5) | 0.33640 (14) | 0.0347 (7) | |
| C2 | 0.3769 (6) | 0.0346 (6) | 0.29976 (16) | 0.0413 (8) | |
| H2A | 0.2649 | −0.0291 | 0.3127 | 0.050* | |
| C3 | 0.3712 (7) | 0.0865 (7) | 0.24370 (18) | 0.0505 (10) | |
| H3A | 0.2543 | 0.0571 | 0.2190 | 0.061* | |
| C4 | 0.5367 (8) | 0.1816 (6) | 0.22353 (17) | 0.0515 (10) | |
| H4A | 0.5311 | 0.2154 | 0.1857 | 0.062* | |
| C5 | 0.7099 (7) | 0.2255 (5) | 0.26028 (16) | 0.0456 (9) | |
| H5A | 0.8212 | 0.2899 | 0.2471 | 0.055* | |
| C6 | 0.7191 (6) | 0.1741 (5) | 0.31665 (15) | 0.0366 (7) | |
| C7 | 0.9058 (6) | 0.2144 (6) | 0.35786 (15) | 0.0416 (8) | |
| H7A | 0.9982 | 0.1052 | 0.3604 | 0.050* | |
| H7B | 0.9816 | 0.3225 | 0.3450 | 0.050* | |
| C8 | 0.7367 (8) | 0.4460 (6) | 0.4157 (2) | 0.0588 (12) | |
| H8A | 0.8373 | 0.5433 | 0.4104 | 0.088* | |
| H8B | 0.6837 | 0.4636 | 0.4515 | 0.088* | |
| H8C | 0.6240 | 0.4539 | 0.3861 | 0.088* | |
| C9 | 1.0127 (6) | 0.2409 (7) | 0.45859 (18) | 0.0538 (11) | |
| H9A | 1.1119 | 0.3397 | 0.4537 | 0.081* | |
| H9B | 1.0786 | 0.1191 | 0.4562 | 0.081* | |
| H9C | 0.9620 | 0.2539 | 0.4948 | 0.081* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Te | 0.03675 (13) | 0.04765 (15) | 0.03311 (13) | 0.00064 (11) | 0.00659 (8) | 0.00140 (11) |
| Cl | 0.0484 (5) | 0.0601 (6) | 0.0536 (6) | −0.0112 (5) | 0.0102 (4) | 0.0036 (5) |
| N | 0.0340 (14) | 0.0375 (15) | 0.0403 (16) | 0.0027 (12) | 0.0043 (12) | −0.0043 (13) |
| C1 | 0.0397 (17) | 0.0331 (15) | 0.0320 (16) | 0.0061 (14) | 0.0069 (13) | −0.0021 (13) |
| C2 | 0.0409 (18) | 0.0428 (19) | 0.0399 (19) | 0.0057 (16) | 0.0039 (14) | −0.0059 (16) |
| C3 | 0.057 (2) | 0.050 (2) | 0.042 (2) | 0.014 (2) | −0.0078 (18) | −0.0079 (18) |
| C4 | 0.079 (3) | 0.039 (2) | 0.0348 (19) | 0.010 (2) | 0.0016 (19) | 0.0035 (16) |
| C5 | 0.066 (3) | 0.0367 (18) | 0.0357 (19) | −0.0026 (18) | 0.0112 (17) | 0.0009 (15) |
| C6 | 0.0438 (18) | 0.0320 (16) | 0.0348 (17) | −0.0002 (14) | 0.0071 (14) | −0.0014 (14) |
| C7 | 0.0404 (18) | 0.049 (2) | 0.0364 (18) | −0.0033 (16) | 0.0097 (14) | −0.0003 (16) |
| C8 | 0.071 (3) | 0.043 (2) | 0.061 (3) | 0.007 (2) | 0.000 (2) | −0.012 (2) |
| C9 | 0.042 (2) | 0.074 (3) | 0.043 (2) | −0.007 (2) | −0.0038 (17) | −0.004 (2) |
| Te—C1 | 2.116 (3) | C4—H4A | 0.9300 |
| Te—N | 2.355 (3) | C5—C6 | 1.387 (5) |
| Te—Cl | 2.5657 (11) | C5—H5A | 0.9300 |
| N—C9 | 1.471 (5) | C6—C7 | 1.500 (5) |
| N—C7 | 1.486 (5) | C7—H7A | 0.9700 |
| N—C8 | 1.487 (5) | C7—H7B | 0.9700 |
| C1—C2 | 1.385 (5) | C8—H8A | 0.9600 |
| C1—C6 | 1.397 (5) | C8—H8B | 0.9600 |
| C2—C3 | 1.383 (6) | C8—H8C | 0.9600 |
| C2—H2A | 0.9300 | C9—H9A | 0.9600 |
| C3—C4 | 1.387 (7) | C9—H9B | 0.9600 |
| C3—H3A | 0.9300 | C9—H9C | 0.9600 |
| C4—C5 | 1.382 (6) | ||
| C1—Te—N | 76.45 (13) | C6—C5—H5A | 119.8 |
| C1—Te—Cl | 92.14 (10) | C5—C6—C1 | 119.7 (4) |
| N—Te—Cl | 168.59 (8) | C5—C6—C7 | 122.4 (3) |
| C9—N—C7 | 111.0 (3) | C1—C6—C7 | 117.9 (3) |
| C9—N—C8 | 110.7 (3) | N—C7—C6 | 109.6 (3) |
| C7—N—C8 | 111.7 (3) | N—C7—H7A | 109.7 |
| C9—N—Te | 111.3 (3) | C6—C7—H7A | 109.7 |
| C7—N—Te | 102.7 (2) | N—C7—H7B | 109.7 |
| C8—N—Te | 109.3 (3) | C6—C7—H7B | 109.7 |
| C2—C1—C6 | 120.1 (3) | H7A—C7—H7B | 108.2 |
| C2—C1—Te | 125.0 (3) | N—C8—H8A | 109.5 |
| C6—C1—Te | 114.9 (3) | N—C8—H8B | 109.5 |
| C3—C2—C1 | 119.3 (4) | H8A—C8—H8B | 109.5 |
| C3—C2—H2A | 120.4 | N—C8—H8C | 109.5 |
| C1—C2—H2A | 120.4 | H8A—C8—H8C | 109.5 |
| C2—C3—C4 | 121.2 (4) | H8B—C8—H8C | 109.5 |
| C2—C3—H3A | 119.4 | N—C9—H9A | 109.5 |
| C4—C3—H3A | 119.4 | N—C9—H9B | 109.5 |
| C5—C4—C3 | 119.3 (4) | H9A—C9—H9B | 109.5 |
| C5—C4—H4A | 120.4 | N—C9—H9C | 109.5 |
| C3—C4—H4A | 120.4 | H9A—C9—H9C | 109.5 |
| C4—C5—C6 | 120.5 (4) | H9B—C9—H9C | 109.5 |
| C4—C5—H5A | 119.8 | ||
| C1—Te—N—C9 | −152.7 (3) | C2—C3—C4—C5 | −0.2 (6) |
| Cl—Te—N—C9 | −154.3 (3) | C3—C4—C5—C6 | 0.4 (6) |
| C1—Te—N—C7 | −33.9 (2) | C4—C5—C6—C1 | −0.5 (6) |
| Cl—Te—N—C7 | −35.5 (5) | C4—C5—C6—C7 | 178.5 (4) |
| C1—Te—N—C8 | 84.8 (3) | C2—C1—C6—C5 | 0.3 (5) |
| Cl—Te—N—C8 | 83.2 (5) | Te—C1—C6—C5 | −178.4 (3) |
| N—Te—C1—C2 | −160.8 (3) | C2—C1—C6—C7 | −178.7 (3) |
| Cl—Te—C1—C2 | 18.9 (3) | Te—C1—C6—C7 | 2.6 (4) |
| N—Te—C1—C6 | 17.8 (2) | C9—N—C7—C6 | 163.4 (3) |
| Cl—Te—C1—C6 | −162.5 (3) | C8—N—C7—C6 | −72.6 (4) |
| C6—C1—C2—C3 | −0.1 (5) | Te—N—C7—C6 | 44.4 (3) |
| Te—C1—C2—C3 | 178.4 (3) | C5—C6—C7—N | 145.9 (3) |
| C1—C2—C3—C4 | 0.0 (6) | C1—C6—C7—N | −35.1 (5) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9C···Cli | 0.96 | 2.89 | 3.822 (5) | 163. |
| Symmetry codes: (i) −x+1, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9C···Cli | 0.96 | 2.89 | 3.822 (5) | 163. |
| Symmetry codes: (i) −x+1, −y, −z+1. |
RJB acknowledges the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer. HBS acknowledges the DST (New Delhi) for funding. PR acknowledges the CSIR for a fellowship.
Engman, L., Wojton, A., Oleksyn, B. J. & Sliwinski, J. (2004). Phosphorus Sulfur Silicon Relat. Elem. 179, 285–292.
Kaur, R., Singh, H. B. & Butcher, R. J. (1995). Organometallics, 14, 4755–4763.
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Singh, H. B., Sudha, N., West, A. A. & Hamor, T. A. (1990). J. Chem. Soc. Dalton Trans. pp. 907–913.
Attempts to synthesize protonated bis[2-(dimethylaminomethyl)phenyl]ditelluride resulted in the formation of 2-(N,N-dimethylaminomethyl)phenyl)tellurenyl chloride, C9H12ClNTe, (1) a compound which had been previously prepared via a different method (Singh et al., 1990). The structure of C9H12ClNTe contains isolated molecules with no close Te···Cl intermolecular contacts, and is chemically related to a previously published structure (Engman, et al., 2004), even though it had been prepared by the same method as the title compound. However, in this case the compound has crystallized in a centrosymmetric space group, unlike the previously published structure (Engman, et al., 2004) which contained enantiomerically pure, chiral molecules. In all other aspects the metrical parameters are similar. The molecules arelinked into dimers by C—H···Cl interactions.