The crystal structure of di-tert-butylhydroxidoiodidotin(IV), [Sn(C4H9)2I(OH)] or tBu2Sn(OH)I, consists of centrosymmetric dimers exhibiting the characteristic structural features of diorganotin(IV)-hydroxide-halides.
Supporting information
CCDC reference: 2172420
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.016
- wR factor = 0.037
- Data-to-parameter ratio = 25.9
checkCIF/PLATON results
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Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ... Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 4 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
6 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al.,
2020); software used to prepare material for publication: publCIF (Westrip, 2010).
Di-
tert-butylhydroxidoiodidotin(IV)
top
Crystal data top
[Sn(C4H9)2I(OH)] | F(000) = 712 |
Mr = 376.82 | Dx = 2.048 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4903 (4) Å | Cell parameters from 9771 reflections |
b = 10.8848 (5) Å | θ = 2.4–29.2° |
c = 13.5107 (6) Å | µ = 4.58 mm−1 |
β = 101.881 (2)° | T = 100 K |
V = 1221.85 (10) Å3 | Block, yellow |
Z = 4 | 0.24 × 0.12 × 0.09 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2761 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.064 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 28.0°, θmin = 2.6° |
Tmin = 0.457, Tmax = 0.715 | h = −11→11 |
48755 measured reflections | k = −14→13 |
2950 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.016 | w = 1/[σ2(Fo2) + (0.0075P)2 + 1.3137P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.037 | (Δ/σ)max = 0.003 |
S = 1.08 | Δρmax = 0.85 e Å−3 |
2950 reflections | Δρmin = −0.49 e Å−3 |
114 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick 2015, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00139 (11) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.31459 (2) | 0.21150 (2) | 0.53430 (2) | 0.01973 (5) | |
Sn1 | 0.06240 (2) | 0.37120 (2) | 0.43364 (2) | 0.01006 (5) | |
C21 | 0.1879 (2) | 0.44568 (19) | 0.32082 (15) | 0.0137 (4) | |
C22 | 0.2375 (3) | 0.3375 (2) | 0.26155 (17) | 0.0193 (5) | |
H22A | 0.1409 | 0.2956 | 0.2247 | 0.032 (4)* | |
H22B | 0.3027 | 0.2798 | 0.3086 | 0.032 (4)* | |
H22C | 0.3004 | 0.3679 | 0.2135 | 0.032 (4)* | |
C23 | 0.3377 (3) | 0.5141 (2) | 0.37485 (17) | 0.0190 (4) | |
H23A | 0.3972 | 0.5445 | 0.3249 | 0.023 (4)* | |
H23B | 0.4064 | 0.4582 | 0.4218 | 0.023 (4)* | |
H23C | 0.3059 | 0.5835 | 0.4126 | 0.023 (4)* | |
C24 | 0.0749 (3) | 0.5304 (2) | 0.24902 (16) | 0.0190 (4) | |
H24A | 0.1273 | 0.5569 | 0.1944 | 0.027 (4)* | |
H24B | 0.0495 | 0.6025 | 0.2863 | 0.027 (4)* | |
H24C | −0.0246 | 0.4863 | 0.2203 | 0.027 (4)* | |
C11 | −0.1328 (3) | 0.23567 (19) | 0.40781 (16) | 0.0153 (4) | |
C12 | −0.2895 (3) | 0.2973 (2) | 0.35517 (19) | 0.0233 (5) | |
H12A | −0.2754 | 0.3331 | 0.2910 | 0.029 (4)* | |
H12B | −0.3175 | 0.3623 | 0.3987 | 0.029 (4)* | |
H12C | −0.3759 | 0.2362 | 0.3421 | 0.029 (4)* | |
C13 | −0.0867 (3) | 0.1346 (2) | 0.34001 (18) | 0.0214 (5) | |
H13A | −0.0798 | 0.1697 | 0.2742 | 0.028 (4)* | |
H13B | −0.1687 | 0.0699 | 0.3304 | 0.028 (4)* | |
H13C | 0.0178 | 0.0997 | 0.3721 | 0.028 (4)* | |
C14 | −0.1500 (3) | 0.1809 (2) | 0.50925 (18) | 0.0236 (5) | |
H14A | −0.2351 | 0.1185 | 0.4979 | 0.029 (4)* | |
H14B | −0.1781 | 0.2461 | 0.5526 | 0.029 (4)* | |
H14C | −0.0480 | 0.1431 | 0.5423 | 0.029 (4)* | |
O1 | 0.09927 (17) | 0.46366 (13) | 0.56977 (10) | 0.0150 (3) | |
H1 | 0.1841 | 0.4272 | 0.6190 | 0.070 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02092 (9) | 0.01756 (8) | 0.01844 (8) | 0.00750 (5) | −0.00125 (6) | 0.00161 (5) |
Sn1 | 0.01100 (8) | 0.00881 (8) | 0.01046 (7) | 0.00010 (5) | 0.00239 (5) | −0.00050 (5) |
C21 | 0.0164 (10) | 0.0130 (10) | 0.0128 (9) | −0.0014 (8) | 0.0051 (8) | −0.0012 (8) |
C22 | 0.0235 (12) | 0.0175 (11) | 0.0188 (11) | −0.0001 (9) | 0.0085 (9) | −0.0039 (9) |
C23 | 0.0180 (11) | 0.0196 (11) | 0.0206 (11) | −0.0048 (9) | 0.0067 (9) | −0.0020 (9) |
C24 | 0.0236 (11) | 0.0176 (11) | 0.0158 (10) | 0.0020 (9) | 0.0040 (9) | 0.0041 (8) |
C11 | 0.0170 (10) | 0.0131 (10) | 0.0171 (10) | −0.0037 (8) | 0.0064 (8) | −0.0040 (8) |
C12 | 0.0153 (11) | 0.0226 (12) | 0.0308 (13) | −0.0029 (9) | 0.0018 (9) | −0.0057 (10) |
C13 | 0.0223 (12) | 0.0173 (11) | 0.0255 (12) | −0.0036 (9) | 0.0070 (9) | −0.0083 (9) |
C14 | 0.0295 (13) | 0.0198 (12) | 0.0250 (12) | −0.0054 (10) | 0.0135 (10) | 0.0012 (9) |
O1 | 0.0166 (7) | 0.0147 (7) | 0.0126 (7) | 0.0047 (6) | 0.0004 (6) | −0.0021 (6) |
Geometric parameters (Å, º) top
I1—Sn1 | 2.8734 (2) | C24—H24C | 0.9800 |
Sn1—O1 | 2.0631 (1) | C11—C12 | 1.528 (3) |
Sn1—C21 | 2.187 (2) | C11—C14 | 1.529 (3) |
Sn1—C11 | 2.193 (2) | C11—C13 | 1.533 (3) |
Sn1—O1i | 2.2564 (1) | C12—H12A | 0.9800 |
C21—C23 | 1.524 (3) | C12—H12B | 0.9800 |
C21—C24 | 1.526 (3) | C12—H12C | 0.9800 |
C21—C22 | 1.531 (3) | C13—H13A | 0.9800 |
C22—H22A | 0.9800 | C13—H13B | 0.9800 |
C22—H22B | 0.9800 | C13—H13C | 0.9800 |
C22—H22C | 0.9800 | C14—H14A | 0.9800 |
C23—H23A | 0.9800 | C14—H14B | 0.9800 |
C23—H23B | 0.9800 | C14—H14C | 0.9800 |
C23—H23C | 0.9800 | O1—Sn1i | 2.2563 (14) |
C24—H24A | 0.9800 | O1—H1 | 0.9600 |
C24—H24B | 0.9800 | | |
| | | |
O1—Sn1—C21 | 115.73 (7) | C21—C24—H24C | 109.5 |
O1—Sn1—C11 | 116.17 (7) | H24A—C24—H24C | 109.5 |
C21—Sn1—C11 | 126.81 (8) | H24B—C24—H24C | 109.5 |
O1—Sn1—O1i | 67.02 (6) | C12—C11—C14 | 110.71 (19) |
C21—Sn1—O1i | 94.13 (7) | C12—C11—C13 | 109.99 (18) |
C11—Sn1—O1i | 95.51 (7) | C14—C11—C13 | 109.84 (19) |
O1—Sn1—I1 | 84.93 (4) | C12—C11—Sn1 | 109.60 (14) |
C21—Sn1—I1 | 97.57 (5) | C14—C11—Sn1 | 109.16 (14) |
C11—Sn1—I1 | 97.67 (6) | C13—C11—Sn1 | 107.47 (14) |
O1i—Sn1—I1 | 151.94 (4) | C11—C12—H12A | 109.5 |
C23—C21—C24 | 111.25 (18) | C11—C12—H12B | 109.5 |
C23—C21—C22 | 109.50 (17) | H12A—C12—H12B | 109.5 |
C24—C21—C22 | 109.69 (17) | C11—C12—H12C | 109.5 |
C23—C21—Sn1 | 109.00 (13) | H12A—C12—H12C | 109.5 |
C24—C21—Sn1 | 109.55 (13) | H12B—C12—H12C | 109.5 |
C22—C21—Sn1 | 107.78 (14) | C11—C13—H13A | 109.5 |
C21—C22—H22A | 109.5 | C11—C13—H13B | 109.5 |
C21—C22—H22B | 109.5 | H13A—C13—H13B | 109.5 |
H22A—C22—H22B | 109.5 | C11—C13—H13C | 109.5 |
C21—C22—H22C | 109.5 | H13A—C13—H13C | 109.5 |
H22A—C22—H22C | 109.5 | H13B—C13—H13C | 109.5 |
H22B—C22—H22C | 109.5 | C11—C14—H14A | 109.5 |
C21—C23—H23A | 109.5 | C11—C14—H14B | 109.5 |
C21—C23—H23B | 109.5 | H14A—C14—H14B | 109.5 |
H23A—C23—H23B | 109.5 | C11—C14—H14C | 109.5 |
C21—C23—H23C | 109.5 | H14A—C14—H14C | 109.5 |
H23A—C23—H23C | 109.5 | H14B—C14—H14C | 109.5 |
H23B—C23—H23C | 109.5 | Sn1—O1—Sn1i | 112.98 (6) |
C21—C24—H24A | 109.5 | Sn1—O1—H1 | 111.7 |
C21—C24—H24B | 109.5 | Sn1i—O1—H1 | 135.3 |
H24A—C24—H24B | 109.5 | | |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···I1 | 0.96 | 2.93 | 3.3862 (14) | 111 |