Tetra­bromido­[4-(triphenyl­phosphanyl­oxy)but­yl]tellurium acetonitrile monosolvate

Närhi, S.M.; Oilunkaniemi, R.; Laitinen, R.S.

doi:10.1107/S1600536812051707

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page m88

doi:10.1107/S1600536812051707

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Tetrabromido[4-(triphenylphosphanyloxy)butyl]tellurium acetonitrile monosolvate

Sari M. Närhi,^a Raija Oilunkaniemi ^a ^* and Risto S. Laitinen ^a

^aDepartment of Chemistry, PO Box 3000, FI-90014 University of Oulu, Finland
^*Correspondence e-mail: raija.oilunkaniemi@oulu.fi

(Received 10 December 2012; accepted 22 December 2012; online 9 January 2013)

In the title compound, [TeBr₄(C₂₂H₂₃OP)]·CH₃CN, the Te atom exhibits a square-pyramidal coordination with an apical Te—C bond and four basal Te—Br bonds. The conformation of the aliphatic C—C—C—C chain is gauche [torsion angle = −67.7 (8)°]. A weak C—H⋯Br interaction helps to establish the conformation. In the crystal, there is a weak secondary bonding interaction [Te⋯N = 3.456 (11) Å] between the Te atom and the N atom of the solvent molecule, which completes a distorted TeNCBr₄ octahedron. Inversion dimers linked by pairs of C—H⋯Br interactions are also observed.

Related literature

For the formation of Ph₃PO(CH₂)₄TeBr₄ and the structure of the dichloromethane monosolvate, see: Kunnari et al. (2001 ). For Te⋯N interactions, see: Cozzolino et al. (2011 ); Pauling (1960 ).

Experimental

Crystal data

[TeBr₄(C₂₂H₂₃OP)]·C₂H₃N
M_r = 822.67
Monoclinic, P 2₁ /n
a = 9.3195 (19) Å
b = 13.899 (3) Å
c = 21.962 (4) Å
β = 94.92 (3)°
V = 2834.3 (10) Å³
Z = 4
Mo Kα radiation
μ = 6.76 mm⁻¹
T = 150 K
0.10 × 0.10 × 0.05 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.551, T_max = 0.729
11187 measured reflections
4684 independent reflections
3714 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.135
S = 1.07
4684 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Selected bond lengths (Å)

Te1—C4	2.176 (7)
Te1—Br2	2.6652 (10)
Te1—Br4	2.6814 (11)
Te1—Br1	2.6944 (11)
Te1—Br3	2.7201 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯Br1	0.99	2.82	3.450 (7)	122
C26—H26⋯Br3ⁱ	0.95	2.75	3.619 (8)	152
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: COLLECT (Bruker, 2008 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 2012 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051707/hb7012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051707/hb7012Isup2.hkl

checkCIF report

Comment top

The formation of Ph₃PO(CH₂)₄TeBr₄ has been reported earlier by us (Kunnari et al. 2001). The formally zwitterionic compound was isolated by treating TeBr₄ with an equimolar amount of triphenylphosphine in tetrahydrofuran. The compound was crystallized from dichloromethane and its molecular structure was determined as a dichloromethane solvate. The title compound was recrystallized from acetonitrile and consequently contains acetonitrile solvent molecules. It is isomorphic with the CH₂Cl₂ solvate.

The molecular structure of the title compound indicating the numbering of the atoms is shown in Fig. 1. The Te—Br bond lengths range from 2.6652 (10) to 2.7201 (10) Å. The Te—C bond length is 2.176 (7) Å and the P—O bond length is 1.568 (5) Å. These can be compared to the bond lengths in the corresponding CH₂Cl₂ solvate in which the Te—Br bond lengths range 2.6776 (8) - 2.6952 (9) Å, Te—C bond length is 2.177 (6) Å, and P—O bond length is 1.581 (4) Å (Kunnari et al. 2001).

The closest internuclear contact from tellurium atom to the nitrogen atom of the solvent molecule is 3.456 (11) Å expanding the square pyramidal coordination polyhedron into a distorted octahedron. This is typical for Te^···N secondary bonding interactions (Cozzolino et al. 2011). Interestingly, the Te^..N interaction is stronger [Pauling (1960) bond order is 0.15] compared to the Te^..Cl interaction in the CH₂Cl₂ solvate (Kunnari et al. 2001), for which the contact is 4.175 (3) Å corresponding to the Pauling bond order of only 0.09. This is also reflected in the C—Te—E (E = N, Cl) bond angles which are 165.0 (3) and 144.0 (1) °, respectively.

Intra- and intermolecular hydrogen bonds link the zwitterions into a three- dimensional network, as shown in Fig. 2. The shortest intermolecular C—H^···Br contacts span a range of 2.75 (1)–2.96 (1) Å and the short C—H^..N contacts are 2.68 (1) and 2.96 (1) Å.

Related literature top

For the formation of Ph₃PO(CH₂)₄TeBr₄ and the structure of the dichloromethane monosolvate see Kunnari et al. (2001). For Te···N interactions, see: Cozzolino et al. (2011); Pauling (1960).

Experimental top

Yellow plates of the title compound were obtained from the acetonitrile solution of Ph₃PO(CH₂)₄TeBr₄ by slow evaporation of the solvent.

Computing details top

Data collection: COLLECT (Bruker, 2008); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at 50% probability.
	Fig. 2. The packing of the zwitterions and the solvent indicating the short inter- and intramolecular contacts < 3.00 Å.

Tetrabromo[4-(triphenylphosphanyloxy)butyl]tellurium acetonitrile monosolvate top

Crystal data top

[TeBr₄(C₂₂H₂₃OP)]·C₂H₃N	F(000) = 1568
M_r = 822.67	D_x = 1.928 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3714 reflections
a = 9.3195 (19) Å	θ = 2.3–25.0°
b = 13.899 (3) Å	µ = 6.76 mm⁻¹
c = 21.962 (4) Å	T = 150 K
β = 94.92 (3)°	Plate, yellow
V = 2834.3 (10) Å³	0.10 × 0.10 × 0.05 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	4684 independent reflections
Radiation source: fine-focus sealed tube	3714 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ scans, and ω scans with κ offsets	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −11→10
T_min = 0.551, T_max = 0.729	k = −15→16
11187 measured reflections	l = −24→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0606P)² + 8.1058P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4684 reflections	Δρ_max = 0.88 e Å⁻³
291 parameters	Δρ_min = −0.79 e Å⁻³
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (3)

Crystal data top

[TeBr₄(C₂₂H₂₃OP)]·C₂H₃N	V = 2834.3 (10) Å³
M_r = 822.67	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3195 (19) Å	µ = 6.76 mm⁻¹
b = 13.899 (3) Å	T = 150 K
c = 21.962 (4) Å	0.10 × 0.10 × 0.05 mm
β = 94.92 (3)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	4684 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	3714 reflections with I > 2σ(I)
T_min = 0.551, T_max = 0.729	R_int = 0.073
11187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.07	Δρ_max = 0.88 e Å⁻³
4684 reflections	Δρ_min = −0.79 e Å⁻³
291 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Te1	0.55868 (5)	0.29462 (3)	−0.09855 (2)	0.02466 (19)
Br1	0.40006 (9)	0.21866 (6)	−0.19512 (3)	0.0335 (2)
Br2	0.50893 (9)	0.14024 (6)	−0.03152 (4)	0.0356 (2)
Br3	0.59404 (9)	0.45190 (6)	−0.16944 (4)	0.0388 (2)
Br4	0.71342 (9)	0.37800 (6)	−0.00436 (4)	0.0380 (2)
P1	0.0720 (2)	0.26347 (14)	0.10968 (8)	0.0248 (4)
O1	0.0848 (5)	0.2852 (3)	0.0403 (2)	0.0275 (11)
C1	0.1193 (8)	0.3822 (5)	0.0189 (3)	0.0288 (17)
H1A	0.2167	0.4017	0.0361	0.035*
H1B	0.0488	0.4295	0.0321	0.035*
C2	0.1130 (8)	0.3783 (6)	−0.0504 (3)	0.0303 (17)
H2A	0.1202	0.4447	−0.0660	0.036*
H2B	0.0177	0.3527	−0.0660	0.036*
C3	0.2297 (7)	0.3172 (5)	−0.0764 (3)	0.0269 (16)
H3A	0.2302	0.2520	−0.0582	0.032*
H3B	0.2090	0.3108	−0.1212	0.032*
C4	0.3740 (8)	0.3632 (5)	−0.0625 (3)	0.0285 (17)
H4A	0.3930	0.3671	−0.0175	0.034*
H4B	0.3680	0.4300	−0.0781	0.034*
C11	−0.0254 (8)	0.1540 (5)	0.1093 (3)	0.0281 (16)
C12	−0.0930 (9)	0.1166 (6)	0.0554 (4)	0.041 (2)
H12	−0.0853	0.1485	0.0176	0.049*
C13	−0.1719 (10)	0.0320 (6)	0.0577 (4)	0.049 (2)
H13	−0.2202	0.0065	0.0214	0.059*
C14	−0.1801 (9)	−0.0147 (6)	0.1125 (4)	0.042 (2)
H14	−0.2315	−0.0737	0.1134	0.050*
C15	−0.1146 (9)	0.0226 (6)	0.1663 (4)	0.0385 (19)
H15	−0.1236	−0.0098	0.2039	0.046*
C16	−0.0364 (9)	0.1066 (5)	0.1656 (3)	0.0329 (18)
H16	0.0093	0.1323	0.2024	0.039*
C21	−0.0209 (8)	0.3556 (5)	0.1456 (3)	0.0284 (17)
C22	−0.1690 (8)	0.3508 (5)	0.1482 (3)	0.0304 (17)
H22	−0.2204	0.2960	0.1323	0.036*
C23	−0.2421 (9)	0.4246 (6)	0.1736 (3)	0.0371 (19)
H23	−0.3432	0.4202	0.1758	0.045*
C24	−0.1682 (9)	0.5055 (6)	0.1959 (3)	0.0356 (19)
H24	−0.2189	0.5570	0.2128	0.043*
C25	−0.0214 (9)	0.5113 (6)	0.1936 (4)	0.039 (2)
H25	0.0288	0.5665	0.2096	0.046*
C26	0.0539 (9)	0.4379 (5)	0.1684 (3)	0.0340 (18)
H26	0.1551	0.4428	0.1665	0.041*
C31	0.2498 (8)	0.2506 (5)	0.1460 (3)	0.0294 (17)
C32	0.2787 (9)	0.2633 (6)	0.2092 (3)	0.0364 (19)
H32	0.2041	0.2809	0.2339	0.044*
C33	0.4197 (9)	0.2496 (6)	0.2351 (4)	0.040 (2)
H33	0.4415	0.2593	0.2777	0.048*
C34	0.5280 (9)	0.2221 (6)	0.1991 (4)	0.042 (2)
H34	0.6233	0.2132	0.2172	0.050*
C35	0.4976 (9)	0.2076 (6)	0.1372 (4)	0.045 (2)
H35	0.5709	0.1867	0.1128	0.054*
C36	0.3595 (8)	0.2239 (6)	0.1110 (4)	0.0371 (19)
H36	0.3397	0.2165	0.0681	0.044*
N1	0.8684 (11)	0.1649 (8)	−0.1169 (5)	0.075 (3)
C5	0.7977 (12)	0.1025 (8)	−0.1349 (5)	0.052 (2)
C6	0.7060 (13)	0.0250 (8)	−0.1577 (6)	0.073 (3)
H6A	0.6813	−0.0153	−0.1235	0.110*
H6B	0.7565	−0.0139	−0.1864	0.110*
H6C	0.6177	0.0515	−0.1788	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Te1	0.0209 (3)	0.0284 (3)	0.0246 (3)	0.00017 (19)	0.00156 (19)	−0.00170 (19)
Br1	0.0357 (5)	0.0387 (5)	0.0257 (4)	−0.0025 (3)	0.0001 (3)	−0.0071 (3)
Br2	0.0376 (5)	0.0335 (5)	0.0356 (4)	0.0018 (3)	0.0013 (3)	0.0055 (3)
Br3	0.0325 (5)	0.0403 (5)	0.0441 (5)	−0.0040 (4)	0.0061 (3)	0.0102 (4)
Br4	0.0295 (5)	0.0459 (5)	0.0370 (4)	−0.0024 (4)	−0.0062 (3)	−0.0085 (4)
P1	0.0229 (10)	0.0277 (10)	0.0240 (9)	−0.0022 (8)	0.0038 (7)	0.0036 (8)
O1	0.029 (3)	0.027 (3)	0.026 (3)	0.000 (2)	0.001 (2)	0.004 (2)
C1	0.034 (4)	0.027 (4)	0.026 (4)	−0.001 (3)	0.003 (3)	0.007 (3)
C2	0.030 (4)	0.034 (4)	0.027 (4)	−0.002 (3)	0.002 (3)	0.002 (3)
C3	0.023 (4)	0.036 (4)	0.023 (4)	0.000 (3)	0.008 (3)	−0.002 (3)
C4	0.024 (4)	0.029 (4)	0.033 (4)	0.001 (3)	0.005 (3)	−0.001 (3)
C11	0.032 (4)	0.025 (4)	0.027 (4)	−0.001 (3)	0.003 (3)	0.002 (3)
C12	0.048 (5)	0.043 (5)	0.029 (4)	−0.010 (4)	−0.008 (4)	0.003 (4)
C13	0.055 (6)	0.044 (5)	0.046 (5)	−0.015 (4)	−0.017 (4)	0.000 (4)
C14	0.027 (5)	0.030 (4)	0.067 (6)	−0.005 (3)	0.001 (4)	−0.001 (4)
C15	0.043 (5)	0.032 (4)	0.043 (5)	−0.008 (4)	0.014 (4)	0.000 (4)
C16	0.040 (5)	0.034 (4)	0.026 (4)	−0.004 (4)	0.009 (3)	−0.001 (3)
C21	0.031 (4)	0.031 (4)	0.022 (4)	0.003 (3)	−0.002 (3)	−0.003 (3)
C22	0.026 (4)	0.036 (4)	0.029 (4)	−0.004 (3)	0.001 (3)	0.001 (3)
C23	0.037 (5)	0.043 (5)	0.033 (4)	0.004 (4)	0.012 (4)	0.008 (4)
C24	0.053 (6)	0.033 (4)	0.022 (4)	0.014 (4)	0.009 (4)	0.001 (3)
C25	0.047 (5)	0.031 (4)	0.036 (4)	−0.001 (4)	−0.002 (4)	−0.001 (4)
C26	0.039 (5)	0.029 (4)	0.035 (4)	0.002 (3)	0.007 (4)	0.003 (3)
C31	0.027 (4)	0.026 (4)	0.034 (4)	−0.003 (3)	−0.002 (3)	0.009 (3)
C32	0.040 (5)	0.039 (5)	0.029 (4)	0.003 (4)	−0.004 (3)	0.004 (4)
C33	0.036 (5)	0.036 (5)	0.045 (5)	−0.006 (4)	−0.008 (4)	0.013 (4)
C34	0.030 (5)	0.049 (5)	0.045 (5)	−0.003 (4)	−0.006 (4)	0.014 (4)
C35	0.028 (5)	0.058 (6)	0.051 (5)	−0.008 (4)	0.006 (4)	0.004 (4)
C36	0.024 (4)	0.047 (5)	0.040 (4)	−0.001 (4)	0.002 (3)	0.005 (4)
N1	0.071 (7)	0.074 (7)	0.084 (7)	0.010 (6)	0.031 (6)	−0.015 (6)
C5	0.054 (6)	0.050 (6)	0.054 (6)	0.021 (5)	0.015 (5)	0.006 (5)
C6	0.071 (8)	0.057 (7)	0.088 (8)	0.016 (6)	−0.016 (6)	−0.019 (6)

Geometric parameters (Å, º) top

Te1—C4	2.176 (7)	C15—H15	0.9500
Te1—Br2	2.6652 (10)	C16—H16	0.9500
Te1—Br4	2.6814 (11)	C21—C22	1.387 (11)
Te1—Br1	2.6944 (11)	C21—C26	1.410 (10)
Te1—Br3	2.7201 (10)	C22—C23	1.375 (11)
P1—O1	1.568 (5)	C22—H22	0.9500
P1—C21	1.769 (7)	C23—C24	1.386 (11)
P1—C11	1.772 (7)	C23—H23	0.9500
P1—C31	1.785 (8)	C24—C25	1.375 (12)
O1—C1	1.473 (8)	C24—H24	0.9500
C1—C2	1.518 (10)	C25—C26	1.380 (11)
C1—H1A	0.9900	C25—H25	0.9500
C1—H1B	0.9900	C26—H26	0.9500
C2—C3	1.529 (10)	C31—C36	1.382 (11)
C2—H2A	0.9900	C31—C32	1.403 (10)
C2—H2B	0.9900	C32—C33	1.399 (11)
C3—C4	1.497 (10)	C32—H32	0.9500
C3—H3A	0.9900	C33—C34	1.388 (12)
C3—H3B	0.9900	C33—H33	0.9500
C4—H4A	0.9900	C34—C35	1.380 (12)
C4—H4B	0.9900	C34—H34	0.9500
C11—C12	1.394 (10)	C35—C36	1.383 (11)
C11—C16	1.412 (10)	C35—H35	0.9500
C12—C13	1.390 (11)	C36—H36	0.9500
C12—H12	0.9500	N1—C5	1.140 (14)
C13—C14	1.375 (12)	C5—C6	1.438 (15)
C13—H13	0.9500	C6—H6A	0.9800
C14—C15	1.384 (12)	C6—H6B	0.9800
C14—H14	0.9500	C6—H6C	0.9800
C15—C16	1.378 (11)

C4—Te1—Br2	88.4 (2)	C13—C14—H14	119.4
C4—Te1—Br4	85.4 (2)	C15—C14—H14	119.4
Br2—Te1—Br4	91.68 (3)	C16—C15—C14	120.2 (8)
C4—Te1—Br1	93.5 (2)	C16—C15—H15	119.9
Br2—Te1—Br1	90.55 (3)	C14—C15—H15	119.9
Br4—Te1—Br1	177.46 (3)	C15—C16—C11	118.9 (7)
C4—Te1—Br3	89.7 (2)	C15—C16—H16	120.5
Br2—Te1—Br3	176.86 (3)	C11—C16—H16	120.5
Br4—Te1—Br3	90.61 (3)	C22—C21—C26	119.2 (7)
Br1—Te1—Br3	87.11 (3)	C22—C21—P1	120.7 (6)
O1—P1—C21	112.0 (3)	C26—C21—P1	120.0 (6)
O1—P1—C11	104.1 (3)	C23—C22—C21	120.7 (7)
C21—P1—C11	110.7 (4)	C23—C22—H22	119.7
O1—P1—C31	107.9 (3)	C21—C22—H22	119.7
C21—P1—C31	110.2 (4)	C22—C23—C24	120.0 (8)
C11—P1—C31	111.8 (3)	C22—C23—H23	120.0
C1—O1—P1	121.6 (4)	C24—C23—H23	120.0
O1—C1—C2	107.2 (6)	C25—C24—C23	120.0 (7)
O1—C1—H1A	110.3	C25—C24—H24	120.0
C2—C1—H1A	110.3	C23—C24—H24	120.0
O1—C1—H1B	110.3	C24—C25—C26	120.9 (8)
C2—C1—H1B	110.3	C24—C25—H25	119.5
H1A—C1—H1B	108.5	C26—C25—H25	119.5
C1—C2—C3	115.3 (6)	C25—C26—C21	119.3 (8)
C1—C2—H2A	108.5	C25—C26—H26	120.4
C3—C2—H2A	108.5	C21—C26—H26	120.4
C1—C2—H2B	108.5	C36—C31—C32	119.7 (7)
C3—C2—H2B	108.5	C36—C31—P1	118.8 (6)
H2A—C2—H2B	107.5	C32—C31—P1	121.4 (6)
C4—C3—C2	110.0 (6)	C33—C32—C31	118.6 (8)
C4—C3—H3A	109.7	C33—C32—H32	120.7
C2—C3—H3A	109.7	C31—C32—H32	120.7
C4—C3—H3B	109.7	C34—C33—C32	120.6 (8)
C2—C3—H3B	109.7	C34—C33—H33	119.7
H3A—C3—H3B	108.2	C32—C33—H33	119.7
C3—C4—Te1	117.6 (5)	C35—C34—C33	120.3 (8)
C3—C4—H4A	107.9	C35—C34—H34	119.9
Te1—C4—H4A	107.9	C33—C34—H34	119.9
C3—C4—H4B	107.9	C34—C35—C36	119.5 (8)
Te1—C4—H4B	107.9	C34—C35—H35	120.3
H4A—C4—H4B	107.2	C36—C35—H35	120.3
C12—C11—C16	120.6 (7)	C31—C36—C35	121.3 (8)
C12—C11—P1	121.2 (6)	C31—C36—H36	119.4
C16—C11—P1	118.2 (6)	C35—C36—H36	119.4
C13—C12—C11	119.1 (7)	N1—C5—C6	178.8 (11)
C13—C12—H12	120.4	C5—C6—H6A	109.5
C11—C12—H12	120.4	C5—C6—H6B	109.5
C14—C13—C12	120.0 (8)	H6A—C6—H6B	109.5
C14—C13—H13	120.0	C5—C6—H6C	109.5
C12—C13—H13	120.0	H6A—C6—H6C	109.5
C13—C14—C15	121.1 (8)	H6B—C6—H6C	109.5

C21—P1—O1—C1	41.9 (6)	C31—P1—C21—C22	−148.6 (6)
C11—P1—O1—C1	161.5 (5)	O1—P1—C21—C26	−84.7 (6)
C31—P1—O1—C1	−79.6 (6)	C11—P1—C21—C26	159.7 (6)
P1—O1—C1—C2	−176.3 (5)	C31—P1—C21—C26	35.5 (7)
O1—C1—C2—C3	−67.3 (8)	C26—C21—C22—C23	−1.0 (11)
C1—C2—C3—C4	−67.7 (8)	P1—C21—C22—C23	−176.9 (6)
C2—C3—C4—Te1	−176.9 (5)	C21—C22—C23—C24	1.1 (12)
Br2—Te1—C4—C3	−62.1 (5)	C22—C23—C24—C25	−1.0 (11)
Br4—Te1—C4—C3	−153.9 (6)	C23—C24—C25—C26	0.9 (12)
Br1—Te1—C4—C3	28.3 (6)	C24—C25—C26—C21	−0.8 (12)
Br3—Te1—C4—C3	115.4 (5)	C22—C21—C26—C25	0.9 (11)
O1—P1—C11—C12	−11.4 (8)	P1—C21—C26—C25	176.8 (6)
C21—P1—C11—C12	109.2 (7)	O1—P1—C31—C36	−24.5 (7)
C31—P1—C11—C12	−127.6 (7)	C21—P1—C31—C36	−147.1 (6)
O1—P1—C11—C16	170.5 (6)	C11—P1—C31—C36	89.3 (7)
C21—P1—C11—C16	−69.0 (7)	O1—P1—C31—C32	158.1 (6)
C31—P1—C11—C16	54.2 (7)	C21—P1—C31—C32	35.5 (7)
C16—C11—C12—C13	0.1 (13)	C11—P1—C31—C32	−88.1 (7)
P1—C11—C12—C13	−178.0 (7)	C36—C31—C32—C33	0.9 (11)
C11—C12—C13—C14	−1.3 (14)	P1—C31—C32—C33	178.3 (6)
C12—C13—C14—C15	2.1 (14)	C31—C32—C33—C34	−1.3 (12)
C13—C14—C15—C16	−1.7 (13)	C32—C33—C34—C35	−0.1 (13)
C14—C15—C16—C11	0.5 (12)	C33—C34—C35—C36	2.1 (13)
C12—C11—C16—C15	0.3 (12)	C32—C31—C36—C35	1.1 (12)
P1—C11—C16—C15	178.5 (6)	P1—C31—C36—C35	−176.3 (6)
O1—P1—C21—C22	91.2 (7)	C34—C35—C36—C31	−2.6 (13)
C11—P1—C21—C22	−24.4 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···Br1	0.99	2.82	3.450 (7)	122
C26—H26···Br3ⁱ	0.95	2.75	3.619 (8)	152

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[TeBr₄(C₂₂H₂₃OP)]·C₂H₃N
M_r	822.67
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	9.3195 (19), 13.899 (3), 21.962 (4)
β (°)	94.92 (3)
V (Å³)	2834.3 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.76
Crystal size (mm)	0.10 × 0.10 × 0.05

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.551, 0.729
No. of measured, independent and observed [I > 2σ(I)] reflections	11187, 4684, 3714
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.135, 1.07
No. of reflections	4684
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.79

Computer programs: COLLECT (Bruker, 2008), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), WinGX (Farrugia, 2012).

Selected bond lengths (Å) top

Te1—C4	2.176 (7)	Te1—Br1	2.6944 (11)
Te1—Br2	2.6652 (10)	Te1—Br3	2.7201 (10)
Te1—Br4	2.6814 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···Br1	0.99	2.82	3.450 (7)	122
C26—H26···Br3ⁱ	0.95	2.75	3.619 (8)	152

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

Financial support from the Academy of Finland is gratefully acknowledged.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GmbH, Bonn, Germany. Google Scholar
Bruker (2008). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cozzolino, A. F., Elder, P. J. & Vargas-Baca, I. (2011). Coord. Chem. Rev. pp. 1426–1438. Web of Science CrossRef Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kunnari, S. M., Oilunkaniemi, R., Laitinen, R. S. & Ahlgren, M. (2001). J. Chem. Soc. Dalton Trans. pp. 3417–3418. Web of Science CSD CrossRef Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol 276. Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Pauling, L. (1960). The Nature of the Chemical Bond, 3rd ed. Ithaca: Cornell University Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Tetra­bromido­[4-(tri­phenyl­phosphanyl­­oxy)but­yl]tellurium aceto­nitrile monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Tetrabromido[4-(triphenylphosphanyloxy)butyl]tellurium acetonitrile monosolvate