Tetra­kis(phenyl­ethyn­yl)tin(IV)

Lahcini, M.; Räisänen, M.T.; Castro, P.M.; Klinga, M.; Leskelä, M.

doi:10.1107/S1600536807050507

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Tetrakis(phenylethynyl)tin(IV)

M. Lahcini, M. T. Räisänen, P. M. Castro, M. Klinga and M. Leskelä

The asymmetric unit of the crystal structure of the title compound, [Sn(C₈H₅)₄], consists of one fourth of a discrete tin complex and one half of another which both possess nearly ideal tetrahedral symmetry; the site symmetries of the two Sn atoms are $\overline4$ and 2. The bond angles at all acetylide C atoms are almost linear. The Sn—C distances [2.076 (6) and 2.065 (6)–2.069 (6) Å in the two complexes) are short when compared to the sum of the covalent radii of C and Sn (2.177 Å), but consistent with another tetrakis(alkynyl)tin complex. The acetylenic bond distances [1.196 (7) and 1.183 (7)–1.207 (7) Å] are consistent with a triple C [triple bond]

C bond. Therefore, despite the short Sn—C distances, the ligands are mainly σ-bonded to the metal. In the solid state, these complexes form a three-dimensional network via agostic C—H interactions as a phenyl proton in the ortho position interacts with the acetylenic carbon in the α position to the tin center.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050507/bt2532sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050507/bt2532Isup2.hkl Contains datablock I

CCDC reference: 667185

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.011 Å
R factor = 0.049
wR factor = 0.078
Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C3     ...       1.47 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12    -   C13    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C22    -   C23    ...       1.46 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28A   ..  C1      ..       2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A   ..  C11     ..       2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A    ..  C21     ..       2.85 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            C1  -SN1 -C1  -C2   -145.00  9.00   3.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            C1  -SN1 -C1  -C2    -24.00  9.00   2.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            C1  -SN1 -C1  -C2     97.00  9.00   4.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            SN1 -C1  -C2  -C3    -37.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            C1  -C2  -C3  -C8     34.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            C1  -C2  -C3  -C4   -150.00 10.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            C21 -SN2 -C11 -C12  -141.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         16
            C21 -SN2 -C11 -C12   100.00  3.00   2.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            C11 -SN2 -C11 -C12   -21.00  3.00   2.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            SN2 -C11 -C12 -C13     2.00 23.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            C11 -C12 -C13 -C18     4.00 21.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            C11 -C12 -C13 -C14    17.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
            C21 -SN2 -C21 -C22   -71.00 13.00   2.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            C11 -SN2 -C21 -C22   168.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            C11 -SN2 -C21 -C22    51.00 13.00   2.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            SN2 -C21 -C22 -C23    53.00 21.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            C21 -C22 -C23 -C28    45.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         34
            C21 -C22 -C23 -C24  -142.00 11.00   1.555   1.555   1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.03

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.60
           From the CIF: _reflns_number_total               4311
           Count of symmetry unique reflns         2253
           Completeness (_total/calc)            191.34%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2058
           Fraction of Friedel pairs measured     0.913
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  29 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
  22 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

There has been much recent interest in tetrakis(alkynyl)tin(IV) as new precursor for preparation of tin-alkoxide and sol-gel chemistry for the preparation of tin-oxide (Jousseaume et al., 1998). Recently, we demonstrated that tetrakis(phenylethynyl)tin(IV) is an efficient initiator for ring-opening polymerization of lactide and ε-caprolactone providing high activity and high molar mass polymers (Lahcini et al., 2004). Here, we describe the crystal structure of tetrakis(phenylethynyl)tin. It crystallized in a tetragonal space group I4, which reflects high symmetry of the molecule. The asymmetric unit cell consists of one fourth of a discrete tin complex (labeled as a Sn1 in Fig. 1) and one half of another one (Sn2) which both posses nearly ideal tetrahedral symmetry. The Sn(1)—C(1)—C(2) (176.5 (5)°) and C(1)—C(2)—C(3) (176.0 (7)°) angles in Sn1 and the Sn(2)—C(11)—C(12) (171.1 (5)°) and C(11)—C(12)—C(13) (178.0 (8)°) as well as the Sn(2)—C(21)—C(22) (177.4 (6)°) and C(21)—C(22)—C(23) (176.2 (8)°) angles in Sn2 illustrate a rather linear coordination of the acetylides on the Sn centers. The Sn—C distances (2.076 Å in Sn1 and 2.065–2.069 Å in Sn2) are short when compared to the sum of the covalent radii of C and Sn (2.177 Å), but coherent with another tetrakis(alkynyl)Sn complex, Me₃Si—C≡C—Sn (2.067 Å) (Dallaire et al., 1993). The acetylenic bond distances (1.196 (7) Å in Sn1 and 1.183 (7)–1.207 (7) Å in Sn2) are consistent with a triple C≡C bond and comparable to previously reported phenylethynyl complexes, e.g. trans-[(NH₃)Ru(C≡ CPh)(Ph₂PCH₂CH₂PPH₂)₂] (1.187 (7) Å) (Touchard et al., 1997) and amidotin porphyrin (TTP)Sn(C≡CPh)₂ (1.197 (3) Å) (Chen & Woo, 1998). Therefore, despite of the short Sn—C distances, the ligands are mainly σ-bonded to the metal. In the solid state these complexes form a three-dimensional network via agostic C—H interactions as illustrated in Fig. 1; a phenyl proton in ortho position interacts with the acetylenic carbon in α position to the tin center (see table of hydrogen bonds).

Related literature top

For related literature, see: Chen & Woo 1998; Dallaire et al. 1993; Jousseaume et al. 1998; Lahcini et al. 2004; Touchard et al. 1997.

For related literature, see: Kottke & Stalke (1993).

Experimental top

The title compound was synthesized according to a published procedure (Dallaire et al., 1993). Treatment of tin tetrachloride with 4 equivalents of phenyllithium in toluene led to a corresponding tetrakis(alkynyl)tin(IV). Crystals suitable for solid state structure determination were obtained by recrystallization from toluene.

Structure description top

For related literature, see: Chen & Woo 1998; Dallaire et al. 1993; Jousseaume et al. 1998; Lahcini et al. 2004; Touchard et al. 1997.

For related literature, see: Kottke & Stalke (1993).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: COLLECT (Nonius, 2002); data reduction: COLLECT (Nonius, 2002); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELX97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELX97 (Sheldrick, 1997).

Figures top

	Fig. 1. A view of tetrakis(phenylethynyl)tin(IV), showing the atom-labelling scheme. Thermal ellipsoids are depicted at 50% propability level. Atoms C11A—C18A and C21A—C28A are generated with (-x,-y,z) and atoms C1AA—C8AA and C1B—C8B with (x,-y,-z) symmetry operator.
	Fig. 2. Intermolecular agostic interactions in the structure of tetrakis(phenylethynyl)tin(IV) are shown as dotted lines. These distances are close to the sum of van der Waals radius of carbon and hydrogen atoms, namely C1—H28A 2.923 Å, C11—H18A (y,-x,1 - z) 2.888 Å and C21—H8A (-x,-y,z) 2.853 Å.

Tetrakis(phenylethynyl)tin(IV) top

Crystal data top

[Sn(C₈H₅)₄]	D_x = 1.384 Mg m⁻³
M_r = 523.17	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 9860 reflections
Hall symbol: I -4	θ = 3.4–27.6°
a = 13.689 (1) Å	µ = 1.03 mm⁻¹
c = 20.098 (1) Å	T = 173 K
V = 3766.1 (4) Å³	Needle, colourless
Z = 6	0.30 × 0.10 × 0.10 mm
F(000) = 1572

Data collection top

Nonius KappaCCD diffractometer	4311 independent reflections
Radiation source: fine-focus sealed tube	2474 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
φ and ω scans	θ_max = 27.6°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→17
T_min = 0.747, T_max = 0.904	k = −17→10
9860 measured reflections	l = −25→17

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.01P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
4311 reflections	Δρ_max = 0.75 e Å⁻³
224 parameters	Δρ_min = −0.78 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2075 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

[Sn(C₈H₅)₄]	Z = 6
M_r = 523.17	Mo Kα radiation
Tetragonal, I4	µ = 1.03 mm⁻¹
a = 13.689 (1) Å	T = 173 K
c = 20.098 (1) Å	0.30 × 0.10 × 0.10 mm
V = 3766.1 (4) Å³

Data collection top

Nonius KappaCCD diffractometer	4311 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2474 reflections with I > 2σ(I)
T_min = 0.747, T_max = 0.904	R_int = 0.070
9860 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.75 e Å⁻³
S = 0.93	Δρ_min = −0.78 e Å⁻³
4311 reflections	Absolute structure: Flack (1983), 2075 Friedel pairs
224 parameters	Absolute structure parameter: 0.00 (3)
0 restraints

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
Sn1	0.0000	0.0000	0.0000	0.02556 (18)
C1	0.1148 (4)	0.0423 (4)	0.0610 (2)	0.0315 (16)
C2	0.1773 (5)	0.0677 (4)	0.0988 (3)	0.0268 (15)
C3	0.2494 (6)	0.1040 (7)	0.1469 (5)	0.028 (2)
C4	0.3493 (5)	0.0952 (5)	0.1299 (3)	0.0392 (16)
H4A	0.3687	0.0664	0.0890	0.047*
C5	0.4185 (7)	0.1299 (7)	0.1749 (4)	0.049 (2)
H5A	0.4860	0.1278	0.1640	0.058*
C6	0.3886 (6)	0.1674 (5)	0.2356 (3)	0.0466 (19)
H6A	0.4361	0.1904	0.2664	0.056*
C7	0.2913 (6)	0.1719 (5)	0.2520 (3)	0.0474 (18)
H7A	0.2712	0.1975	0.2938	0.057*
C8	0.2228 (5)	0.1384 (5)	0.2065 (3)	0.0328 (17)
H8A	0.1555	0.1400	0.2180	0.039*
Sn2	0.0000	0.0000	0.312944 (19)	0.03048 (15)
C11	0.1112 (4)	0.0463 (4)	0.3751 (3)	0.0328 (15)
C12	0.1652 (5)	0.0739 (4)	0.4170 (3)	0.0345 (16)
C13	0.2279 (7)	0.1074 (7)	0.4695 (5)	0.033 (3)
C14	0.3267 (6)	0.1345 (5)	0.4593 (3)	0.0381 (19)
H14A	0.3544	0.1289	0.4161	0.046*
C15	0.3827 (5)	0.1684 (5)	0.5105 (5)	0.048 (2)
H15A	0.4491	0.1853	0.5027	0.058*
C16	0.3428 (5)	0.1786 (5)	0.5744 (3)	0.0395 (17)
H16A	0.3823	0.2022	0.6098	0.047*
C17	0.2456 (5)	0.1544 (5)	0.5862 (3)	0.0458 (19)
H17A	0.2175	0.1623	0.6291	0.055*
C18	0.1915 (7)	0.1186 (7)	0.5338 (4)	0.039 (2)
H18A	0.1256	0.1005	0.5419	0.047*
C21	0.0450 (4)	−0.1128 (5)	0.2520 (3)	0.0374 (17)
C22	0.0675 (5)	−0.1793 (5)	0.2157 (3)	0.0389 (17)
C23	0.0911 (7)	−0.2566 (7)	0.1682 (4)	0.034 (2)
C24	0.0938 (6)	−0.3541 (6)	0.1889 (4)	0.072 (3)
H24A	0.0782	−0.3718	0.2333	0.086*
C25	0.1202 (9)	−0.4245 (7)	0.1420 (4)	0.082 (4)
H25A	0.1194	−0.4915	0.1543	0.098*
C26	0.1471 (5)	−0.3998 (5)	0.0790 (3)	0.050 (2)
H26A	0.1649	−0.4495	0.0483	0.060*
C27	0.1488 (4)	−0.3049 (5)	0.0597 (3)	0.0363 (16)
H27A	0.1680	−0.2878	0.0158	0.044*
C28	0.1220 (5)	−0.2327 (5)	0.1051 (3)	0.0315 (17)
H28A	0.1252	−0.1660	0.0923	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0240 (3)	0.0240 (3)	0.0287 (4)	0.000	0.000	0.000
C1	0.032 (4)	0.039 (4)	0.024 (4)	−0.007 (3)	−0.001 (3)	0.000 (3)
C2	0.030 (4)	0.025 (4)	0.025 (4)	0.000 (3)	0.001 (3)	−0.001 (3)
C3	0.020 (5)	0.028 (5)	0.037 (6)	0.002 (4)	−0.001 (4)	0.017 (4)
C4	0.027 (4)	0.051 (5)	0.040 (4)	0.003 (4)	0.004 (4)	−0.001 (4)
C5	0.040 (5)	0.060 (6)	0.046 (6)	0.000 (4)	−0.001 (4)	0.014 (4)
C6	0.050 (5)	0.030 (4)	0.060 (5)	−0.012 (4)	−0.025 (4)	0.008 (3)
C7	0.059 (6)	0.036 (4)	0.046 (4)	−0.004 (4)	−0.009 (4)	0.003 (3)
C8	0.027 (4)	0.039 (5)	0.033 (4)	−0.003 (4)	−0.004 (3)	0.005 (3)
Sn2	0.0280 (8)	0.0333 (8)	0.0302 (3)	0.0035 (9)	0.000	0.000
C11	0.033 (4)	0.045 (4)	0.020 (3)	−0.004 (3)	0.003 (3)	0.009 (3)
C12	0.034 (5)	0.037 (4)	0.032 (4)	0.007 (3)	0.003 (3)	0.007 (3)
C13	0.037 (6)	0.021 (5)	0.043 (5)	0.005 (4)	0.001 (4)	−0.002 (3)
C14	0.040 (6)	0.036 (5)	0.039 (4)	0.007 (4)	0.005 (4)	0.000 (3)
C15	0.038 (4)	0.042 (4)	0.065 (7)	−0.009 (3)	−0.005 (5)	0.000 (5)
C16	0.043 (5)	0.031 (4)	0.045 (4)	0.007 (4)	−0.011 (4)	−0.006 (3)
C17	0.062 (6)	0.038 (5)	0.037 (4)	−0.004 (4)	0.004 (4)	−0.002 (3)
C18	0.034 (6)	0.028 (5)	0.055 (6)	0.000 (5)	−0.005 (4)	−0.004 (3)
C21	0.035 (5)	0.043 (5)	0.034 (4)	0.004 (4)	−0.003 (3)	−0.001 (3)
C22	0.032 (5)	0.049 (5)	0.036 (4)	0.009 (4)	0.003 (3)	0.009 (3)
C23	0.016 (4)	0.043 (6)	0.044 (7)	0.002 (4)	0.009 (3)	−0.002 (4)
C24	0.114 (8)	0.043 (6)	0.058 (6)	0.010 (5)	0.029 (6)	0.005 (5)
C25	0.153 (10)	0.032 (6)	0.061 (7)	0.008 (6)	0.031 (6)	0.002 (5)
C26	0.070 (6)	0.031 (5)	0.050 (5)	0.008 (4)	0.011 (4)	−0.003 (3)
C27	0.025 (4)	0.054 (5)	0.030 (4)	0.005 (3)	0.001 (3)	0.005 (3)
C28	0.030 (4)	0.029 (5)	0.035 (4)	0.010 (3)	−0.006 (3)	0.000 (3)

Geometric parameters (Å, º) top

Sn1—C1	2.076 (6)	C13—C14	1.417 (11)
Sn1—C1ⁱ	2.076 (6)	C14—C15	1.364 (10)
Sn1—C1ⁱⁱ	2.076 (6)	C14—H14A	0.9500
Sn1—C1ⁱⁱⁱ	2.076 (6)	C15—C16	1.404 (12)
C1—C2	1.196 (7)	C15—H15A	0.9500
C2—C3	1.467 (10)	C16—C17	1.391 (9)
C3—C8	1.339 (10)	C16—H16A	0.9500
C3—C4	1.415 (10)	C17—C18	1.379 (10)
C4—C5	1.393 (10)	C17—H17A	0.9500
C4—H4A	0.9500	C18—H18A	0.9500
C5—C6	1.387 (9)	C21—C22	1.207 (7)
C5—H5A	0.9500	C22—C23	1.461 (11)
C6—C7	1.374 (8)	C23—C28	1.377 (10)
C6—H6A	0.9500	C23—C24	1.398 (12)
C7—C8	1.387 (8)	C24—C25	1.396 (10)
C7—H7A	0.9500	C24—H24A	0.9500
C8—H8A	0.9500	C25—C26	1.360 (9)
Sn2—C21	2.065 (6)	C25—H25A	0.9500
Sn2—C21ⁱⁱ	2.065 (6)	C26—C27	1.356 (8)
Sn2—C11	2.069 (6)	C26—H26A	0.9500
Sn2—C11ⁱⁱ	2.069 (6)	C27—C28	1.394 (8)
C11—C12	1.183 (7)	C27—H27A	0.9500
C12—C13	1.435 (10)	C28—H28A	0.9500
C13—C18	1.393 (8)

C1—Sn1—C1ⁱ	110.43 (15)	C14—C13—C12	123.3 (8)
C1—Sn1—C1ⁱⁱ	107.6 (3)	C15—C14—C13	121.1 (7)
C1ⁱ—Sn1—C1ⁱⁱ	110.43 (15)	C15—C14—H14A	119.4
C1—Sn1—C1ⁱⁱⁱ	110.43 (15)	C13—C14—H14A	119.4
C1ⁱ—Sn1—C1ⁱⁱⁱ	107.6 (3)	C14—C15—C16	120.4 (7)
C1ⁱⁱ—Sn1—C1ⁱⁱⁱ	110.43 (15)	C14—C15—H15A	119.8
C2—C1—Sn1	176.5 (5)	C16—C15—H15A	119.8
C1—C2—C3	176.0 (7)	C17—C16—C15	120.3 (6)
C8—C3—C4	120.5 (8)	C17—C16—H16A	119.9
C8—C3—C2	121.8 (8)	C15—C16—H16A	119.9
C4—C3—C2	117.5 (8)	C18—C17—C16	118.0 (7)
C5—C4—C3	118.2 (8)	C18—C17—H17A	121.0
C5—C4—H4A	120.9	C16—C17—H17A	121.0
C3—C4—H4A	120.9	C17—C18—C13	123.7 (9)
C6—C5—C4	119.8 (8)	C17—C18—H18A	118.1
C6—C5—H5A	120.1	C13—C18—H18A	118.1
C4—C5—H5A	120.1	C22—C21—Sn2	177.4 (6)
C7—C6—C5	121.0 (7)	C21—C22—C23	176.2 (8)
C7—C6—H6A	119.5	C28—C23—C24	119.5 (9)
C5—C6—H6A	119.5	C28—C23—C22	119.8 (8)
C6—C7—C8	118.8 (6)	C24—C23—C22	120.2 (8)
C6—C7—H7A	120.6	C25—C24—C23	117.7 (9)
C8—C7—H7A	120.6	C25—C24—H24A	121.1
C3—C8—C7	121.6 (7)	C23—C24—H24A	121.1
C3—C8—H8A	119.2	C26—C25—C24	121.8 (9)
C7—C8—H8A	119.2	C26—C25—H25A	119.1
C21—Sn2—C21ⁱⁱ	107.2 (3)	C24—C25—H25A	119.1
C21—Sn2—C11	111.6 (2)	C27—C26—C25	120.6 (7)
C21ⁱⁱ—Sn2—C11	110.4 (2)	C27—C26—H26A	119.7
C21—Sn2—C11ⁱⁱ	110.4 (2)	C25—C26—H26A	119.7
C21ⁱⁱ—Sn2—C11ⁱⁱ	111.6 (2)	C26—C27—C28	119.1 (6)
C11—Sn2—C11ⁱⁱ	105.7 (3)	C26—C27—H27A	120.4
C12—C11—Sn2	171.1 (5)	C28—C27—H27A	120.4
C11—C12—C13	178.0 (8)	C23—C28—C27	121.0 (7)
C18—C13—C14	116.6 (8)	C23—C28—H28A	119.5
C18—C13—C12	120.1 (9)	C27—C28—H28A	119.5

C1ⁱ—Sn1—C1—C2	−145 (9)	C12—C13—C14—C15	178.2 (8)
C1ⁱⁱ—Sn1—C1—C2	−24 (9)	C13—C14—C15—C16	−1.0 (11)
C1ⁱⁱⁱ—Sn1—C1—C2	97 (9)	C14—C15—C16—C17	−0.2 (10)
Sn1—C1—C2—C3	−37 (17)	C15—C16—C17—C18	1.4 (10)
C1—C2—C3—C8	34 (11)	C16—C17—C18—C13	−1.5 (13)
C1—C2—C3—C4	−150 (10)	C14—C13—C18—C17	0.4 (16)
C8—C3—C4—C5	−4.6 (12)	C12—C13—C18—C17	−177.0 (7)
C2—C3—C4—C5	179.6 (7)	C21ⁱⁱ—Sn2—C21—C22	−71 (13)
C3—C4—C5—C6	3.0 (11)	C11—Sn2—C21—C22	168 (13)
C4—C5—C6—C7	−0.7 (11)	C11ⁱⁱ—Sn2—C21—C22	51 (13)
C5—C6—C7—C8	−0.2 (10)	Sn2—C21—C22—C23	53 (21)
C4—C3—C8—C7	3.8 (12)	C21—C22—C23—C28	45 (12)
C2—C3—C8—C7	179.5 (7)	C21—C22—C23—C24	−142 (11)
C6—C7—C8—C3	−1.4 (10)	C28—C23—C24—C25	−5.4 (14)
C21—Sn2—C11—C12	−141 (3)	C22—C23—C24—C25	−177.7 (9)
C21ⁱⁱ—Sn2—C11—C12	100 (3)	C23—C24—C25—C26	3.1 (16)
C11ⁱⁱ—Sn2—C11—C12	−21 (3)	C24—C25—C26—C27	−0.2 (15)
Sn2—C11—C12—C13	2 (23)	C25—C26—C27—C28	−0.4 (11)
C11—C12—C13—C18	4 (21)	C24—C23—C28—C27	5.1 (13)
C11—C12—C13—C14	−173 (100)	C22—C23—C28—C27	177.4 (6)
C18—C13—C14—C15	0.9 (14)	C26—C27—C28—C23	−2.1 (10)

Symmetry codes: (i) y, −x, −z; (ii) −x, −y, z; (iii) −y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···C1	0.95	2.92	3.869 (9)	174
C18—H18A···C11^iv	0.95	2.89	3.736 (11)	149
C8—H8A···C21ⁱⁱ	0.95	2.85	3.795 (9)	171

Symmetry codes: (ii) −x, −y, z; (iv) −y, x, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(C₈H₅)₄]
M_r	523.17
Crystal system, space group	Tetragonal, I4
Temperature (K)	173
a, c (Å)	13.689 (1), 20.098 (1)
V (Å³)	3766.1 (4)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.747, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	9860, 4311, 2474
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.078, 0.93
No. of reflections	4311
No. of parameters	224
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.78
Absolute structure	Flack (1983), 2075 Friedel pairs
Absolute structure parameter	0.00 (3)

Computer programs: COLLECT (Nonius, 2002), SIR2002 (Burla et al., 2003), SHELX97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···C1	0.95	2.92	3.869 (9)	173.7
C18—H18A···C11ⁱ	0.95	2.89	3.736 (11)	149.4
C8—H8A···C21ⁱⁱ	0.95	2.85	3.795 (9)	171.2

Symmetry codes: (i) −y, x, −z+1; (ii) −x, −y, z.

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