Chlorido{2-[(dimethyl-amino)-meth-yl]phenyl-κN,C}tellurium.

The crystal structure of the title compound, C(9)H(12)ClNTe, contains isolated mol-ecules with no close Te⋯Cl inter-molecular contacts and has the same composition as a previously published structure [Engman et al. (2004 ▶). Phospho-rus 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 enanti-omerically pure chiral mol-ecules. In all other aspects, the metrical parameters are similar. The mol-ecules with a T-shaped coordination environment about the Te atom are linked into dimers by C-H⋯Cl inter-actions.

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 = 297.25

Monoclinic,

a = 6.4514 (6) Å

b = 7.0287 (7) Å

c = 23.847 (2) Å

β = 95.967 (9)°

V = 1075.49 (17) Å3

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.096

S = 1.20

3587 reflections

111 parameters

H-atom parameters constrained

Δρmax = 2.25 e Å−3

Δρmin = −0.98 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054328/pk2376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054328/pk2376Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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.

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⋯Cli	0.96	2.89	3.822 (5)	163

Symmetry code: (i) .