Chlorido{2-[(di­methyl­amino)­meth­yl]phenyl-κ²N,C¹}tellurium

The 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—H⋯Cl inter­actions.

Related literature

For a related structure, see: Engman et al. (2004). For related syntheses, see: Singh et al. (1990); Kaur et al. (1995).

Experimental

Crystal data

• C₉H₁₂ClNTe

• M_r = 297.25

• Monoclinic, P 2₁ /n

• a = 6.4514 (6) Å

• b = 7.0287 (7) Å

• c = 23.847 (2) Å

• β = 95.967 (9)°

• V = 1075.49 (17) ų

• Z = 4

• Mo Kα radiation

• μ = 2.96 mm⁻¹

• T = 295 K

• 0.45 × 0.36 × 0.12 mm

Data collection

• Oxford Diffraction Xcalibur Ruby Gemini diffractometer

• Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007) T_min = 0.504, T_max = 1.000

• 7778 measured reflections

• 3587 independent reflections

• 2998 reflections with I > 2σ(I)

• R_int = 0.023

Refinement

• R[F² > 2σ(F²)] = 0.043

• wR(F²) = 0.096

• S = 1.20

• 3587 reflections

• 111 parameters

• H-atom parameters constrained

• Δρ_max = 2.25 e Å⁻³

• Δρ_min = −0.98 e Å⁻³

Table 1
Selected bond lengths (Å)

Te—C1	2.116 (3)
Te—N	2.355 (3)
Te—Cl	2.5657 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯Cl^i	0.96	2.89	3.822 (5)	163
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supporting information

S1. Comment

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.

Related literature

For a related structure, see: Engman et al. (2004). For related syntheses, see: Singh et al. (1990); Kaur et al. (1995).

S2. Experimental

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.

S3. Refinement

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 [U_iso(H) = 1.2U_eq(CH, CH₂) [U_iso(H) = 1.5U_eq(CH₃)].

Computing details

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).

Figures

	Fig. 1. Diagram of the contents of the asymmetric unit of C9H12ClNTe. Atomic displacement ellipsoids are drawn at the 30% level.
	Fig. 2. The molecular packing for C9H12ClNTe viewed down the c axis. C—H···Cl secondary interactions are shown by dashed lines.

Chlorido{2-[(dimethylamino)methyl]phenyl-κ²N,C¹}tellurium

Crystal data

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) Å^3	0.45 × 0.36 × 0.12 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3587 independent reflections
Radiation source: fine-focus sealed tube	2998 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 1.2847P] where P = (Fo^2 + 2Fc^2)/3
3587 reflections	(Δ/σ)max = 0.001
111 parameters	Δρmax = 2.25 e Å^−3
0 restraints	Δρmin = −0.98 e Å^−3

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cl^i	0.96	2.89	3.822 (5)	163

Symmetry code: (i) −x+1, −y, −z+1.