1-[(Z)-2-Butyl­tellan­yl-1-chloro­ethen­yl]­cyclo­hex-1-ene

Zukerman-Schpector, J.; Caracelli, I.; Guadagnin, R.C.; Stefani, H.A.; Tiekink, E.R.T.

doi:10.1107/S1600536812007490

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o854-o855

doi:10.1107/S1600536812007490

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1-[(Z)-2-Butyltellanyl-1-chloroethenyl]cyclohex-1-ene

Julio Zukerman-Schpector,^a ^* Ignez Caracelli,^b Rafael Carlos Guadagnin,^c Hélio A. Stefani ^d and Edward R. T. Tiekink ^e

^aDepartmento de Química, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos, SP, Brazil, ^bBioMat – Departmento de Física, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos, SP, Brazil, ^cDepartamento de Ciências Exatas e da Terra, Universidade Federal de São Paulo – Campus Diadema, Rua Professor Artur Ridel, 275, 09972-270 Diadema, SP, Brazil, ^dDepartamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil, and ^eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: julio@power.ufscar.br

(Received 17 February 2012; accepted 19 February 2012; online 24 February 2012)

The Te^II atom in the title molecule, C₁₂H₁₉ClTe, is coordinated in a V-shaped geometry by C atoms derived from the disparate organic substituents. A short intramolecular C—H⋯Cl contact occurs owing to the proximity of the ethene bond in the six-membered ring to the Cl atom. In the crystal, molecules assemble into layers parallel to the ac plane, with the closest interactions between them being of the Te⋯Te type [3.9993 (16) Å].

Related literature

For background to the synthesis, see: Guadagnin et al. (2008 ). For related crystal structures, see: Zeni et al. (1999 ); Barrientos-Astigarraga et al. (2002 ). For ring conformational analysis, see: Cremer & Pople (1975 ). The van der Waals radius for Te was taken from Bondi (1964 ).

Experimental

Crystal data

C₁₂H₁₉ClTe
M_r = 326.32
Triclinic, $[P \overline 1]$
a = 7.666 (3) Å
b = 7.687 (3) Å
c = 12.266 (4) Å
α = 95.499 (15)°
β = 105.060 (14)°
γ = 111.832 (13)°
V = 632.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.53 mm⁻¹
T = 100 K
0.3 × 0.3 × 0.2 mm

Data collection

Rigaku Saturn724 (2 × 2 bin mode) diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.575, T_max = 1.000
3588 measured reflections
2421 independent reflections
2406 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.069
S = 1.17
2421 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.95 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Te—C1	2.077 (3)
Te—C9	2.148 (3)

C1—Te—C9	94.09 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl	0.95	2.56	3.024 (3)	110

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812007490/zl2453sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007490/zl2453Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007490/zl2453Isup3.cml

checkCIF report

Comment top

The title compound, (I), was synthesized by reduction with sodium borohydride of the corresponding 2-halovinyl tellurium dichloride (Guadagnin et al., 2008).

The Te^II atom in (I), Fig. 1, is coordinated by C atoms derived from the organic substituents which define a V-shape, Table 1. The conformation about the C1═C2 bond [1.334 (4) Å] is Z. The ethene bond in the six-membered ring is orientated toward the Cl atom enabling the formation of an intramolecular C—H···Cl interaction, Table 2. The conformation of the six-membered ring is a half-chair with the C5 atom lying 0.641 (5) Å above the plane of the remaining five atoms (r.m.s. deviation = 0.0738 Å), with puckering parameters: q₂ = 0.381 (4) Å and q₃ = 0.311 (4) Å, and amplitudes: Q = 0.492 (4) Å, θ = 50.8 (5) ° and ϕ₂ = 144.3 (6) ° (Cremer & Pople, 1975).

In the crystal packing, molecules assemble into layers parallel to the ac plane, Fig. 2. Within layers, Te···Teⁱ contacts of 3.9993 (16) Å, i.e. less than the sum of the van der Waals radius for Te of 4.4 Å (Bondi, 1964), are noted; i: -x, -y, 2 - z.

Related literature top

For background to the synthesis, see: Guadagnin et al. (2008). For related X-ray structures, see: Zeni et al. (1999); Barrientos-Astigarraga et al. (2002). For ring conformational analysis, see: Cremer & Pople (1975). The van der Waals radius for Te was taken from Bondi (1964).

Experimental top

The title compound was prepared as described in a previous study (Guadagnin et al., 2008). Crystals of (I) were obtained by slow evaporation from its CHCl₃ solution held at room temperature.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents for (I).

1-[(Z)-2-Butyltellanyl-1-chloroethenyl]cyclohex-1-ene top

Crystal data top

C₁₂H₁₉ClTe	Z = 2
M_r = 326.32	F(000) = 320
Triclinic, P1	D_x = 1.713 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.666 (3) Å	Cell parameters from 8499 reflections
b = 7.687 (3) Å	θ = 1.7–29.8°
c = 12.266 (4) Å	µ = 2.53 mm⁻¹
α = 95.499 (15)°	T = 100 K
β = 105.060 (14)°	Irregular, yellow
γ = 111.832 (13)°	0.3 × 0.3 × 0.2 mm
V = 632.8 (4) Å³

Data collection top

Rigaku Saturn724 (2x2 bin mode) diffractometer	2421 independent reflections
Radiation source: fine-focus sealed tube	2406 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 28.5714 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
ω scans	h = −8→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→7
T_min = 0.575, T_max = 1.000	l = −15→14
3588 measured reflections

Refinement top

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) = 0.069	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0343P)² + 1.4833P] where P = (F_o² + 2F_c²)/3
2421 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

C₁₂H₁₉ClTe	γ = 111.832 (13)°
M_r = 326.32	V = 632.8 (4) Å³
Triclinic, P1	Z = 2
a = 7.666 (3) Å	Mo Kα radiation
b = 7.687 (3) Å	µ = 2.53 mm⁻¹
c = 12.266 (4) Å	T = 100 K
α = 95.499 (15)°	0.3 × 0.3 × 0.2 mm
β = 105.060 (14)°

Data collection top

Rigaku Saturn724 (2x2 bin mode) diffractometer	2421 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2406 reflections with I > 2σ(I)
T_min = 0.575, T_max = 1.000	R_int = 0.024
3588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.17	Δρ_max = 0.86 e Å⁻³
2421 reflections	Δρ_min = −0.95 e Å⁻³
128 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
Te	0.10592 (3)	0.26493 (3)	0.970657 (16)	0.01857 (9)
Cl	0.04726 (12)	0.30822 (11)	0.69597 (6)	0.02053 (17)
C10	0.1785 (5)	0.2722 (4)	1.2266 (3)	0.0163 (6)
H10A	0.2188	0.1662	1.2121	0.020*
H10B	0.0323	0.2162	1.2066	0.020*
C2	0.2010 (4)	0.5213 (4)	0.7990 (3)	0.0143 (6)
C4	0.3968 (5)	0.8795 (4)	0.8452 (3)	0.0171 (6)
H4A	0.5292	0.8862	0.8866	0.020*
H4B	0.3262	0.8801	0.9022	0.020*
C3	0.2828 (4)	0.6957 (4)	0.7553 (3)	0.0140 (6)
C6	0.4941 (5)	1.0420 (5)	0.6892 (3)	0.0213 (7)
H6A	0.5152	1.1599	0.6582	0.026*
H6B	0.6223	1.0306	0.7137	0.026*
C11	0.2714 (5)	0.3691 (5)	1.3547 (3)	0.0190 (6)
H11A	0.4177	0.4269	1.3747	0.023*
H11B	0.2292	0.4736	1.3698	0.023*
C9	0.2398 (5)	0.4113 (5)	1.1492 (3)	0.0184 (6)
H9A	0.3860	0.4681	1.1688	0.022*
H9B	0.1980	0.5167	1.1623	0.022*
C5	0.4221 (5)	1.0565 (5)	0.7922 (3)	0.0218 (7)
H5A	0.2936	1.0674	0.7675	0.026*
H5B	0.5188	1.1733	0.8511	0.026*
C12	0.2110 (5)	0.2269 (5)	1.4310 (3)	0.0216 (7)
H12A	0.0667	0.1735	1.4136	0.032*
H12B	0.2755	0.2930	1.5125	0.032*
H12C	0.2521	0.1230	1.4159	0.032*
C8	0.2582 (4)	0.6929 (4)	0.6429 (3)	0.0155 (6)
H8	0.1827	0.5730	0.5896	0.019*
C1	0.2312 (5)	0.5094 (4)	0.9097 (3)	0.0174 (6)
H1	0.3183	0.6237	0.9659	0.021*
C7	0.3432 (5)	0.8689 (5)	0.5959 (3)	0.0183 (6)
H7A	0.2337	0.9002	0.5536	0.022*
H7B	0.4068	0.8400	0.5402	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Te	0.02669 (14)	0.01289 (13)	0.01485 (13)	0.00616 (9)	0.00697 (9)	0.00480 (8)
Cl	0.0278 (4)	0.0125 (3)	0.0153 (3)	0.0037 (3)	0.0050 (3)	0.0000 (3)
C10	0.0192 (14)	0.0146 (14)	0.0144 (14)	0.0061 (12)	0.0055 (12)	0.0032 (11)
C2	0.0138 (13)	0.0120 (13)	0.0167 (14)	0.0048 (11)	0.0054 (11)	0.0016 (11)
C4	0.0169 (14)	0.0158 (15)	0.0147 (14)	0.0026 (12)	0.0055 (11)	0.0026 (11)
C3	0.0147 (13)	0.0152 (14)	0.0144 (14)	0.0076 (11)	0.0061 (11)	0.0039 (11)
C6	0.0216 (15)	0.0183 (16)	0.0213 (16)	0.0039 (13)	0.0074 (13)	0.0084 (13)
C11	0.0221 (15)	0.0183 (15)	0.0153 (15)	0.0078 (13)	0.0049 (12)	0.0037 (12)
C9	0.0218 (15)	0.0181 (15)	0.0138 (14)	0.0061 (12)	0.0054 (12)	0.0055 (12)
C5	0.0265 (16)	0.0158 (15)	0.0193 (16)	0.0057 (13)	0.0064 (13)	0.0018 (12)
C12	0.0237 (16)	0.0266 (17)	0.0172 (15)	0.0112 (14)	0.0085 (13)	0.0073 (13)
C8	0.0165 (14)	0.0138 (14)	0.0151 (14)	0.0058 (11)	0.0043 (11)	0.0022 (11)
C1	0.0220 (15)	0.0123 (14)	0.0152 (14)	0.0047 (12)	0.0052 (12)	0.0036 (11)
C7	0.0214 (15)	0.0171 (15)	0.0148 (14)	0.0051 (12)	0.0069 (12)	0.0056 (12)

Geometric parameters (Å, º) top

Te—C1	2.077 (3)	C6—H6B	0.9900
Te—C9	2.148 (3)	C11—C12	1.526 (4)
Cl—C2	1.750 (3)	C11—H11A	0.9900
C10—C9	1.523 (4)	C11—H11B	0.9900
C10—C11	1.526 (4)	C9—H9A	0.9900
C10—H10A	0.9900	C9—H9B	0.9900
C10—H10B	0.9900	C5—H5A	0.9900
C2—C1	1.334 (4)	C5—H5B	0.9900
C2—C3	1.471 (4)	C12—H12A	0.9800
C4—C3	1.503 (4)	C12—H12B	0.9800
C4—C5	1.532 (5)	C12—H12C	0.9800
C4—H4A	0.9900	C8—C7	1.509 (4)
C4—H4B	0.9900	C8—H8	0.9500
C3—C8	1.338 (4)	C1—H1	0.9500
C6—C7	1.514 (4)	C7—H7A	0.9900
C6—C5	1.515 (5)	C7—H7B	0.9900
C6—H6A	0.9900

C1—Te—C9	94.09 (12)	C10—C9—Te	110.3 (2)
C9—C10—C11	112.3 (3)	C10—C9—H9A	109.6
C9—C10—H10A	109.1	Te—C9—H9A	109.6
C11—C10—H10A	109.1	C10—C9—H9B	109.6
C9—C10—H10B	109.1	Te—C9—H9B	109.6
C11—C10—H10B	109.1	H9A—C9—H9B	108.1
H10A—C10—H10B	107.9	C6—C5—C4	110.7 (3)
C1—C2—C3	126.5 (3)	C6—C5—H5A	109.5
C1—C2—Cl	116.5 (2)	C4—C5—H5A	109.5
C3—C2—Cl	117.0 (2)	C6—C5—H5B	109.5
C3—C4—C5	112.1 (3)	C4—C5—H5B	109.5
C3—C4—H4A	109.2	H5A—C5—H5B	108.1
C5—C4—H4A	109.2	C11—C12—H12A	109.5
C3—C4—H4B	109.2	C11—C12—H12B	109.5
C5—C4—H4B	109.2	H12A—C12—H12B	109.5
H4A—C4—H4B	107.9	C11—C12—H12C	109.5
C8—C3—C2	122.8 (3)	H12A—C12—H12C	109.5
C8—C3—C4	121.6 (3)	H12B—C12—H12C	109.5
C2—C3—C4	115.7 (3)	C3—C8—C7	123.9 (3)
C7—C6—C5	110.2 (3)	C3—C8—H8	118.1
C7—C6—H6A	109.6	C7—C8—H8	118.1
C5—C6—H6A	109.6	C2—C1—Te	126.3 (2)
C7—C6—H6B	109.6	C2—C1—H1	116.9
C5—C6—H6B	109.6	Te—C1—H1	116.9
H6A—C6—H6B	108.1	C8—C7—C6	113.1 (3)
C12—C11—C10	111.6 (3)	C8—C7—H7A	109.0
C12—C11—H11A	109.3	C6—C7—H7A	109.0
C10—C11—H11A	109.3	C8—C7—H7B	109.0
C12—C11—H11B	109.3	C6—C7—H7B	109.0
C10—C11—H11B	109.3	H7A—C7—H7B	107.8
H11A—C11—H11B	108.0

C1—C2—C3—C8	174.6 (3)	C7—C6—C5—C4	61.8 (4)
Cl—C2—C3—C8	−5.9 (4)	C3—C4—C5—C6	−48.2 (4)
C1—C2—C3—C4	−5.6 (4)	C2—C3—C8—C7	−179.0 (3)
Cl—C2—C3—C4	173.9 (2)	C4—C3—C8—C7	1.2 (5)
C5—C4—C3—C8	17.1 (4)	C3—C2—C1—Te	177.3 (2)
C5—C4—C3—C2	−162.7 (3)	Cl—C2—C1—Te	−2.2 (4)
C9—C10—C11—C12	−179.1 (3)	C9—Te—C1—C2	−177.3 (3)
C11—C10—C9—Te	179.5 (2)	C3—C8—C7—C6	12.0 (4)
C1—Te—C9—C10	179.5 (2)	C5—C6—C7—C8	−42.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl	0.95	2.56	3.024 (3)	110

Experimental details

Crystal data
Chemical formula	C₁₂H₁₉ClTe
M_r	326.32
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.666 (3), 7.687 (3), 12.266 (4)
α, β, γ (°)	95.499 (15), 105.060 (14), 111.832 (13)
V (Å³)	632.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.53
Crystal size (mm)	0.3 × 0.3 × 0.2

Data collection
Diffractometer	Rigaku Saturn724 (2x2 bin mode) diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.575, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3588, 2421, 2406
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.069, 1.17
No. of reflections	2421
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.95

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Te—C1	2.077 (3)	Te—C9	2.148 (3)

C1—Te—C9	94.09 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl	0.95	2.56	3.024 (3)	110

Acknowledgements

We thank the Brazilian agencies FAPESP (grant No. 07/59404–2 to HAS), CNPq (grant Nos. 306532/2009-3 to JZS and 308116/2010-0 to IC) and CAPES (grant No. 808/2009 to JZS and IC) for financial support. ERTT thanks the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR/ MOHE/SC/12).

References

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