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The structure of the title compound, [Sn(CH2I)4], consists of Sn situated on a crystallographic fourfold rotatory inversion axis, with pendant iodo­methyl groups whose atoms are in general positions. In the mol­ecule, with overall crystallographically imposed S4 molecular symmetry, there is little, if any, distortion of the tetrahedral environment of Sn, but the bulk of I leads to opening up of the Sn-C-I angle to 112.4 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200274X/wn6084sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680200274X/wn6084Isup2.hkl
Contains datablock I

CCDC reference: 182582

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](Sn-C) = 0.008 Å
  • R factor = 0.038
  • wR factor = 0.105
  • Data-to-parameter ratio = 56.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.112 Tmax scaled 0.104 Tmin scaled 0.046 REFLT_03 From the CIF: _diffrn_reflns_theta_max 32.64 From the CIF: _reflns_number_total 1191 Count of symmetry unique reflns 702 Completeness (_total/calc) 169.66% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 489 Fraction of Friedel pairs measured 0.697 Are heavy atom types Z>Si present yes 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.

Comment top

The asymmetric unit of the title compound, (I), consists of Sn in the 2 b s pecial positions of the space group P421c along with, in the 8 e general positions, C, I and two H atoms of a single representative iodomethyl group. As a consequence, relatively high D2 d symmetry is imposed upon the molecule as a whole, which is shown in Fig. 1, and results in the very compact presentation of symmetry unique bond lengths and angles in Table 2. The bond distances are much as would be anticipated for a molecule of this type. The bond-angle data show that there is no real distortion of the tetrahedral coordination of Sn. However, the Sn1—C1—I1 angle of 112.4 (3)° is clearly attributable to the physical bulk of the I atom.

Experimental top

Compound (I), prepared as described by Burnett et al. (1998) (m.p. 348–349 K) and recrystallized from CHCl3, provided crystals suitable for analysis.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.97 Å, and refined with a riding model, with Uiso = 1.2Ueq(C). The absolute configuration was determined on the basis of 492 Friedel pairs.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecule of (I) showing the labelling scheme. Non-H atoms are shown as 50% ellipsoids and H atoms as small circles. The view is down c of the tetragonal cell. [Symmetry codes: (i) 1 - x, 1 - y, z; (ii) 1 - y, x, 2 - z; (iii) y, 1 - x, 2 - z].
Tetrakis(iodomethyl)stannane top
Crystal data top
[Sn(CH2I)4]Dx = 3.462 Mg m3
Mr = 682.40Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421cCell parameters from 3436 reflections
a = 9.4019 (5) Åθ = 3.1–30.5°
c = 7.4051 (4) ŵ = 11.33 mm1
V = 654.58 (6) Å3T = 298 K
Z = 2Block, colourless
F(000) = 5880.40 × 0.20 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1191 independent reflections
Radiation source: fine-focus sealed tube1044 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ϕ and ω scansθmax = 32.6°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1214
Tmin = 0.416, Tmax = 0.928k = 1413
6440 measured reflectionsl = 1110
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0512P)2 + 1.6332P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1191 reflectionsΔρmax = 0.82 e Å3
21 parametersΔρmin = 1.58 e Å3
0 restraintsAbsolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (18)
Crystal data top
[Sn(CH2I)4]Z = 2
Mr = 682.40Mo Kα radiation
Tetragonal, P421cµ = 11.33 mm1
a = 9.4019 (5) ÅT = 298 K
c = 7.4051 (4) Å0.40 × 0.20 × 0.20 mm
V = 654.58 (6) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1191 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
1044 reflections with I > 2σ(I)
Tmin = 0.416, Tmax = 0.928Rint = 0.030
6440 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.105Δρmax = 0.82 e Å3
S = 1.08Δρmin = 1.58 e Å3
1191 reflectionsAbsolute structure: (Flack, 1983)
21 parametersAbsolute structure parameter: 0.06 (18)
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.

Sn in 2 b s pecial positions of space group P-42 (1)c i.e. molecule has -4 site symmetry. Anisotropic displacement parameters refined for all non-H atoms. H in calculated positions and refined with a riding model.

Absolute structure from 492 Friedel pairs.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.50000.50001.00000.04091 (18)
I10.44403 (8)0.77733 (7)0.68654 (11)0.0749 (2)
C10.3508 (7)0.6061 (8)0.8344 (13)0.0552 (18)
H1A0.27450.64290.90920.066*
H1B0.30980.53850.75020.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0360 (2)0.0360 (2)0.0507 (4)0.0000.0000.000
I10.0710 (4)0.0710 (4)0.0827 (4)0.0096 (3)0.0129 (3)0.0293 (3)
C10.041 (3)0.049 (3)0.075 (5)0.004 (3)0.008 (3)0.006 (3)
Geometric parameters (Å, º) top
Sn1—C12.114 (8)C1—H1A0.9700
I1—C12.135 (8)C1—H1B0.9700
C1—Sn1—C1i109.1 (5)I1—C1—H1A109.1
C1—Sn1—C1ii109.7 (3)Sn1—C1—H1B109.1
Sn1—C1—I1112.4 (3)I1—C1—H1B109.1
Sn1—C1—H1A109.1H1A—C1—H1B107.9
Symmetry codes: (i) x+1, y+1, z; (ii) y+1, x, z+2.

Experimental details

Crystal data
Chemical formula[Sn(CH2I)4]
Mr682.40
Crystal system, space groupTetragonal, P421c
Temperature (K)298
a, c (Å)9.4019 (5), 7.4051 (4)
V3)654.58 (6)
Z2
Radiation typeMo Kα
µ (mm1)11.33
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.416, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
6440, 1191, 1044
Rint0.030
(sin θ/λ)max1)0.759
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.105, 1.08
No. of reflections1191
No. of parameters21
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 1.58
Absolute structure(Flack, 1983)
Absolute structure parameter0.06 (18)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
Sn1—C12.114 (8)I1—C12.135 (8)
C1—Sn1—C1i109.1 (5)Sn1—C1—I1112.4 (3)
C1—Sn1—C1ii109.7 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) y+1, x, z+2.
 

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