2-(Dimethyl-amino-meth-yl)phenyl phenyl telluride.

The title compound, C(15)H(17)NTe, is a heteroleptic Te, N-bidentate ligand having a short Te⋯N contact [2.8079 (16) Å] involving a secondary bonding inter-action between the amino N and Te(II) atoms. The Te-C bond [2.136 (2) Å] trans to the amino group is slightly elongated compared to the other Te-C bond [2.1242 (18) Å] due to the hypervalent inter-action. The bond angle for the trans N-Te-C atoms [164.92 (6)°] deviates significantly from linearity.

Related literature

For Heck and cross-coupling reactions, see: Cella et al. (2006 ▶); Nishibayashi et al. (1996a ▶,b ▶); Zeni & Comasseto (1999 ▶); Zeni et al. (2001 ▶). For intra­molecularly coordinated tellurides, see: Detty et al. (1995 ▶); Drake et al. (2001 ▶); Engman et al. (2004 ▶); Kaur et al. (1995 ▶, 2009 ▶); Menon et al. (1996 ▶); Panda et al. (1999 ▶); Singh et al. (1990 ▶). For van der Waals and covalent radii, see: Bondi (1964 ▶); Cordero et al. (2008 ▶).

Experimental

Crystal data

C15H17NTe

M = 338.90

Monoclinic,

a = 8.5736 (3) Å

b = 13.2472 (5) Å

c = 12.6719 (4) Å

β = 95.933 (3)°

V = 1431.52 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.06 mm−1

T = 110 K

0.49 × 0.41 × 0.27 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.728, T max = 1.000

20642 measured reflections

4836 independent reflections

2926 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.058

S = 0.97

4836 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038161/bt5068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038161/bt5068Isup2.hkl

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

C15H17NTe	F(000) = 664
Mr = 338.90	Dx = 1.572 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8619 reflections
a = 8.5736 (3) Å	θ = 4.9–32.4°
b = 13.2472 (5) Å	µ = 2.06 mm−1
c = 12.6719 (4) Å	T = 110 K
β = 95.933 (3)°	Prism, colorless
V = 1431.52 (9) Å3	0.49 × 0.41 × 0.27 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	4836 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2926 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 32.4°, θmin = 4.9°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −18→19
Tmin = 0.728, Tmax = 1.000	l = −18→18
20642 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0289P)2] where P = (Fo2 + 2Fc2)/3
4836 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Experimental. CrysAlis RED, (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.886656 (14)	0.206826 (9)	0.327530 (10)	0.04605 (6)
C7	1.0873 (2)	−0.00329 (16)	0.33777 (15)	0.0462 (5)
H7A	1.1484	0.0230	0.4025	0.055*
H7B	1.1349	−0.0681	0.3190	0.055*
C1	0.8142 (2)	0.05794 (13)	0.36112 (13)	0.0373 (4)
C2	0.6624 (2)	0.03853 (16)	0.38466 (14)	0.0460 (4)
H2A	0.5888	0.0922	0.3840	0.055*
C3	0.6175 (2)	−0.05790 (16)	0.40897 (16)	0.0533 (5)
H3A	0.5134	−0.0704	0.4249	0.064*
C4	0.7225 (3)	−0.13543 (17)	0.41016 (16)	0.0566 (5)
H4A	0.6923	−0.2016	0.4287	0.068*
C5	0.8725 (3)	−0.11769 (15)	0.38443 (15)	0.0497 (5)
H5A	0.9435	−0.1726	0.3831	0.060*
C6	0.9219 (2)	−0.02150 (14)	0.36041 (14)	0.0395 (4)
N	1.09600 (18)	0.06793 (12)	0.25179 (13)	0.0470 (4)
C8	1.0372 (3)	0.0248 (2)	0.14988 (17)	0.0711 (7)
H8A	0.9302	−0.0002	0.1533	0.107*
H8B	1.1050	−0.0311	0.1329	0.107*
H8C	1.0366	0.0767	0.0947	0.107*
C9	1.2542 (3)	0.1090 (2)	0.2514 (2)	0.0739 (7)
H9A	1.2852	0.1426	0.3192	0.111*
H9B	1.2559	0.1579	0.1934	0.111*
H9C	1.3277	0.0540	0.2412	0.111*
C10	0.6957 (2)	0.27717 (13)	0.39468 (15)	0.0433 (4)
C11	0.5679 (3)	0.31290 (16)	0.32958 (17)	0.0554 (5)
H11A	0.5633	0.3032	0.2550	0.066*
C12	0.4467 (3)	0.36259 (18)	0.37197 (19)	0.0631 (6)
H12A	0.3587	0.3856	0.3266	0.076*
C13	0.4534 (3)	0.37856 (17)	0.47833 (19)	0.0609 (6)
H13A	0.3709	0.4136	0.5071	0.073*
C14	0.5789 (3)	0.34409 (18)	0.54402 (18)	0.0627 (6)
H14A	0.5827	0.3548	0.6184	0.075*
C15	0.6989 (3)	0.29428 (15)	0.50326 (16)	0.0536 (5)
H15B	0.7856	0.2710	0.5497	0.064*

	U11	U22	U33	U12	U13	U23
Te	0.04845 (9)	0.04144 (8)	0.04904 (9)	0.00098 (6)	0.00871 (6)	0.00703 (6)
C7	0.0416 (10)	0.0500 (12)	0.0469 (11)	0.0059 (9)	0.0049 (8)	0.0024 (8)
C1	0.0395 (9)	0.0410 (10)	0.0314 (8)	−0.0007 (8)	0.0031 (7)	−0.0031 (7)
C2	0.0416 (10)	0.0501 (12)	0.0468 (10)	0.0001 (9)	0.0069 (8)	−0.0066 (9)
C3	0.0495 (11)	0.0563 (14)	0.0564 (12)	−0.0160 (10)	0.0169 (9)	−0.0145 (10)
C4	0.0731 (15)	0.0465 (13)	0.0521 (12)	−0.0174 (11)	0.0154 (10)	−0.0081 (9)
C5	0.0640 (13)	0.0393 (11)	0.0463 (11)	0.0035 (10)	0.0080 (9)	−0.0023 (9)
C6	0.0424 (10)	0.0416 (10)	0.0341 (9)	0.0011 (8)	0.0025 (7)	0.0013 (8)
N	0.0431 (9)	0.0491 (10)	0.0503 (9)	0.0027 (7)	0.0128 (7)	0.0049 (8)
C8	0.0833 (16)	0.0851 (19)	0.0466 (13)	0.0158 (15)	0.0149 (11)	0.0025 (12)
C9	0.0555 (13)	0.0756 (18)	0.0948 (18)	−0.0037 (12)	0.0279 (12)	0.0159 (14)
C10	0.0504 (11)	0.0327 (10)	0.0469 (11)	−0.0005 (8)	0.0049 (9)	0.0028 (8)
C11	0.0605 (13)	0.0542 (14)	0.0499 (12)	0.0097 (10)	−0.0022 (10)	−0.0012 (9)
C12	0.0563 (13)	0.0605 (15)	0.0712 (15)	0.0165 (11)	0.0005 (11)	0.0013 (12)
C13	0.0652 (14)	0.0455 (12)	0.0755 (15)	0.0070 (11)	0.0238 (12)	0.0006 (11)
C14	0.0827 (16)	0.0591 (15)	0.0486 (12)	0.0050 (12)	0.0171 (12)	−0.0042 (10)
C15	0.0603 (13)	0.0534 (13)	0.0462 (11)	0.0050 (10)	0.0006 (9)	0.0030 (9)

Te—C1	2.1242 (18)	N—C9	1.462 (3)
Te—C10	2.136 (2)	C8—H8A	0.9800
Te—N	2.8079 (16)	C8—H8B	0.9800
C7—N	1.449 (2)	C8—H8C	0.9800
C7—C6	1.495 (2)	C9—H9A	0.9800
C7—H7A	0.9900	C9—H9B	0.9800
C7—H7B	0.9900	C9—H9C	0.9800
C1—C2	1.389 (3)	C10—C11	1.385 (3)
C1—C6	1.401 (3)	C10—C15	1.392 (3)
C2—C3	1.378 (3)	C11—C12	1.384 (3)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.365 (3)	C12—C13	1.360 (3)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.379 (3)	C13—C14	1.369 (3)
C4—H4A	0.9500	C13—H13A	0.9500
C5—C6	1.387 (3)	C14—C15	1.368 (3)
C5—H5A	0.9500	C14—H14A	0.9500
N—C8	1.454 (3)	C15—H15B	0.9500
C1—Te—C10	94.19 (7)	C9—N—Te	112.55 (14)
C1—Te—N	70.77 (6)	N—C8—H8A	109.5
C10—Te—N	164.92 (6)	N—C8—H8B	109.5
N—C7—C6	111.92 (14)	H8A—C8—H8B	109.5
N—C7—H7A	109.2	N—C8—H8C	109.5
C6—C7—H7A	109.2	H8A—C8—H8C	109.5
N—C7—H7B	109.2	H8B—C8—H8C	109.5
C6—C7—H7B	109.2	N—C9—H9A	109.5
H7A—C7—H7B	107.9	N—C9—H9B	109.5
C2—C1—C6	119.70 (17)	H9A—C9—H9B	109.5
C2—C1—Te	120.99 (14)	N—C9—H9C	109.5
C6—C1—Te	119.30 (13)	H9A—C9—H9C	109.5
C3—C2—C1	120.59 (18)	H9B—C9—H9C	109.5
C3—C2—H2A	119.7	C11—C10—C15	117.82 (19)
C1—C2—H2A	119.7	C11—C10—Te	120.25 (15)
C4—C3—C2	120.08 (19)	C15—C10—Te	121.81 (14)
C4—C3—H3A	120.0	C12—C11—C10	120.7 (2)
C2—C3—H3A	120.0	C12—C11—H11A	119.6
C3—C4—C5	119.9 (2)	C10—C11—H11A	119.6
C3—C4—H4A	120.0	C13—C12—C11	120.2 (2)
C5—C4—H4A	120.0	C13—C12—H12A	119.9
C4—C5—C6	121.48 (19)	C11—C12—H12A	119.9
C4—C5—H5A	119.3	C12—C13—C14	120.0 (2)
C6—C5—H5A	119.3	C12—C13—H13A	120.0
C5—C6—C1	118.17 (17)	C14—C13—H13A	120.0
C5—C6—C7	120.53 (17)	C15—C14—C13	120.4 (2)
C1—C6—C7	121.27 (17)	C15—C14—H14A	119.8
C7—N—C8	111.84 (17)	C13—C14—H14A	119.8
C7—N—C9	111.41 (16)	C14—C15—C10	120.87 (19)
C8—N—C9	112.33 (17)	C14—C15—H15B	119.6
C7—N—Te	94.88 (10)	C10—C15—H15B	119.6
C8—N—Te	112.69 (13)
C10—Te—C1—C2	17.26 (15)	C6—C7—N—Te	45.84 (15)
N—Te—C1—C2	−161.59 (15)	C1—Te—N—C7	−35.48 (10)
C10—Te—C1—C6	−162.12 (13)	C10—Te—N—C7	−39.9 (3)
N—Te—C1—C6	19.02 (12)	C1—Te—N—C8	80.65 (15)
C6—C1—C2—C3	1.0 (3)	C10—Te—N—C8	76.3 (3)
Te—C1—C2—C3	−178.36 (13)	C1—Te—N—C9	−151.08 (15)
C1—C2—C3—C4	0.0 (3)	C10—Te—N—C9	−155.5 (2)
C2—C3—C4—C5	−1.6 (3)	C1—Te—C10—C11	−101.37 (16)
C3—C4—C5—C6	2.2 (3)	N—Te—C10—C11	−97.2 (3)
C4—C5—C6—C1	−1.1 (3)	C1—Te—C10—C15	82.60 (16)
C4—C5—C6—C7	177.09 (17)	N—Te—C10—C15	86.8 (3)
C2—C1—C6—C5	−0.5 (3)	C15—C10—C11—C12	−0.9 (3)
Te—C1—C6—C5	178.88 (13)	Te—C10—C11—C12	−177.11 (17)
C2—C1—C6—C7	−178.66 (16)	C10—C11—C12—C13	1.2 (4)
Te—C1—C6—C7	0.7 (2)	C11—C12—C13—C14	−1.0 (4)
N—C7—C6—C5	140.26 (18)	C12—C13—C14—C15	0.6 (4)
N—C7—C6—C1	−41.6 (2)	C13—C14—C15—C10	−0.3 (4)
C6—C7—N—C8	−71.0 (2)	C11—C10—C15—C14	0.5 (3)
C6—C7—N—C9	162.38 (17)	Te—C10—C15—C14	176.60 (17)

Te—C1	2.1242 (18)
Te—C10	2.136 (2)
Te—N	2.8079 (16)

C1—Te—C10	94.19 (7)
C1—Te—N	70.77 (6)
C10—Te—N	164.92 (6)