In the solid, state diphenyltin(IV)-hydroxide-iodide-N,N′-dimethylpropylene-urea, Ph2Sn(OH) ·DMPU, consists of centrosymmetric dimers exhibiting the characteristic structural features of diorganotin(IV)-hydroxide-halides.
Keywords: crystal structure, diorganotin(IV)-hydroxide-halides, DMPU, hydrogen bonding
Abstract
The title compound, di-μ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2), [Sn(C6H5)2I(OH)]·2C6H12N2O, represents only the second example in the dimeric diorganotin(IV)-hydroxide-halide solvates [R2Sn(OH)Hal]2·2BB with Hal = I. As is usual for this class of compound, dimerization takes place via the oxygen atoms of the hydroxyl groups and leads to a planar, centrosymmetric, four-membered Sn—O ring of rhomboidal shape whose Sn—O distances [2.024 (2)/2.174 (2) Å] are determined by the position (axial or equatorial) of the oxygen atom on the respective trigonal–pyramidal coordinated tin atom while the bond angles are acute [70.74 (8)°] at the tin atoms and obtuse [109.26 (8)°] at the oxygen atoms.
Structure description
Diorganotin(IV)-hydroxide-halides, R2Sn(OH)Hal, which are the first hydrolysis products of diorganotin(IV) dihalides, R2SnHal2, are usually difficult to isolate because of further condensation and aggregation reactions resulting in the formation of different kinds of so-called tetraorganodistannoxanes like (R2SnHal)2O, (R2SnHal)O(R2SnOH), and (R2SnOH)2O, all dimeric in the solid state. Structures of pure diorganotin(IV)-hydroxide-halides are only known for R = p-tolyl and Hal = Br (Lo & Ng, 2009 ▸) as well as for R = tBu and Hal = F, Cl, Br (Puff et al., 1985 ▸), Hal = Cl (Di Nicola et al., 2011 ▸), and Hal = I (Reuter, 2023 ▸). There are also corresponding compounds in combination with hydrogen bonded Brønstedt bases (BB) like R = Ph, Hal = Cl, BB = EtOH (Barba et al., 2007 ▸), BB = quinoline (Anacona et al., 2003 ▸) and R = tBu, Hal = I, BB = DMSO (Reuter & Wilberts, 2014 ▸). The title compound, Ph2Sn(OH)I]2·2DMPU (DMPU is N,N′-dimethylpropylene urea,) (Fig. 1 ▸), represents the second example in the class of dimeric diorganotin(IV)-hydroxide-halide solvates [R2Sn(OH)Hal]2·2BB and Hal = I. A few single crystals of this compound, which was probably formed by reaction with atmospheric moisture, were found by chance in a preparation in which the formation of a 1:2 complex between Ph2SnI2 and DMPU was actually planned.
Figure 1.
The dimeric, centrosymmetric aggregates found in the crystal of [Ph2Sn(OH)I]2·2DMPU, showing the atom numbering of the asymmetric unit. With the exception of the hydrogen atoms, which are shown as spheres of arbitrary radius, all other atoms are drawn with displacement ellipsoids at the 40% probability level. Intermolecular O—H⋯O hydrogen bonds are indicated by dashed sticks in red, black dot = inversion center.
Dimerization takes place according to the same principles as with the previously known compounds via OH bridges between two fivefold, trigonal–pyramidal coordinated tin atoms. In the resulting centrosymmetric and therefore planar, four-membered Sn—O ring (Fig. 2 ▸), the angles are obtuse [109.26 (8)°] at the oxygen atoms and acute [70.74 (8)°] at the tin atoms. Tin–oxygen distances differ depending on whether the OH group at the tin atom in question occupies an equatorial [2.024 (2) Å] or axial position [2.172 (4) Å]. All these values are within the range of the previously determined structures and thus once again confirm the rigidity of this kind of tin–oxygen framework.
Figure 2.
Ball-and-stick model (i = inversion center) of the inorganic framework of the [Ph2Sn(OH)I]2·2DMPU aggregates with selected bond lengths (Å), angles (°) and distances of iodine and hydrogen atoms from the plane of the tin and oxygen atoms in square brackets. Positions of oxygen and iodine atoms within the trigonal–bipyramidal coordination of the tin atoms are labeled by use of the abbreviation ax (= axial) and eq (= equatorial). For clarity, Ph groups are stripped down to the Sn—C bonds drawn as shortened sticks. Intermolecular O—H⋯O hydrogen bonds are indicated by dashed sticks in red.
The tin–iodine distance [2.8278 (2) Å] is longer than the sum [2.78 Å] of the covalent radii (Cordero et al., 2008 ▸) of tin [1.39 Å] and iodine [1.39 Å] due to the axial position of the iodine atom but is shorter than the Sn—I distances in the solvent-free [2.8734 (2) Å] and dmso solvate [2.8852 (2) Å] of the t-butyl compound. The position of the iodine atoms is somewhat outside [±0.278 Å] the plane of the four-membered Sn—O ring. In the case of the two phenyl groups which are in equatorial positions the tin–carbon distances of 2.139 (3) and 2.141 (2) Å are somewhat larger than the tin-carbon distances in the previously mentioned hydroxide-halides with R = Ph [2.119 (3)–2.134 (3) Å, mean value = 2.120 (8) Å].
The phenyl groups do not exhibit any major structural peculiarities, even if they show strong thermal movement, especially in the case of the first one (C11–C16). They are almost planar with greater [Δ = ±0.010 (3) Å] deviations Δ in terms of the distance of the C atoms from the least-squares plane in the first than in the second one [Δ = ±0.004 (2) Å]. The carbon–carbon distances vary from 1.347 (7)–1.402 (5) Å in the first and 1.375 (5)–1.396 (4) Å in the second phenyl group but their mean value of 1.384 (16) Å is in good agreement with the value of 1.380 (13) Å given by Allen et al. (1987 ▸) for this kind of aromatic C—C bonds in phenyl groups. Among the bond angles [118.9 (3)–121.3 (4)°] those at the ipso-carbon atoms are the smallest one [mean value: 119.1 (2)°] in accordance with the so-called ipso-effect (Jones, 1988 ▸).
N,N′-Dimethylpropylene urea, DMPU, is a polar aprotic solvent that is often used in organic synthesis as a substitute for the carcinogenic hexamethylphosphoric acid triamide, HMPTA (Mukhopadhyay & Seebach, 1982 ▸). In crystal structures, it is often found as a complex ligand, co-crystallizate or hydrogen-bonded Lewis base. Typical examples are [Nd(dmpu)6]I3·3DMPU (Lundberg et al., 2010 ▸) and [(iPrSn)12O14(OH)6]Cl2·4DMPU·4H2O (Puff & Reuter, 1989 ▸). In the present structure, the DMPU molecule is connected as hydrogen acceptor with the hydroxyl group of the hydroxide-halide as hydrogen donor. The structural parameters of this cyclic urea derivative are strongly influenced by the urea building unit with almost trigonal–planar-coordinated carbon and nitrogen atoms. Thus, the carbon–nitrogen distances are 1.351 (4)/1.355 (3) Å in the case of the carbon atom of the carbonyl group and 1.452 (4), 1.456 (4) Å in the case of the tetrahedrally coordinated carbon atoms while the endocyclic bond angles at the nitrogen atoms reach 122.2 (2)/122.9 (2)°. The endocyclic carbon–carbon bond lengths are somewhat shorter [1.501 (5)/1.515 (5) Å] than a typical C—C single bond [1.524 (14) Å; Allen et al., 1987 ▸] between sp3-hybridized carbon atoms, but the bond angles [109.4 (3)-109.8 (3)°] correspond very well to this kind of hybridization. The exocyclic C—O bond length of 1.257 (3) Å is slightly elongated in comparison with a C—O double bond between a sp2-hybridized carbon atom and an oxygen atom. Elongation is probably due to the formation of the hydrogen bond with the OH group of the hydroxide-halide. This hydrogen bond is quite strong as the donor–acceptor distances and the nearly linear alignment indicate (Table 1 ▸). As a result of these hydrogen bonds, each strongly polar bond of one molecule is shielded by the apolar parts of the other molecule (Fig. 3 ▸), and the interactions between the adducts are limited to van der Waals bonds.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1⋯O2 | 0.96 | 1.63 | 2.584 (3) | 172 |
Figure 3.
Space-filling model of the [Ph2Sn(OH)I]2·2DMPU aggregates viewed edge-on to the four-membered Sn—O ring and the intermolecular O—H⋯O hydrogen bonds. Color code of the atoms: I = violet, H = white, C = gray, O = red, Sn = brass.
Synthesis and crystallization
Slightly yellowish, block-shaped single crystals of the title compound were found in a micro-scale experiment (Schröder et al., 2024 ▸) in which the 1:2 complex of diphenyltin(IV) iodide, Ph2SnI2, with DMPU should be formed in 96% ethanol as solvent. After prolonged exposure to air, the alcohol had completely evaporated. In the remaining sticky residue, instead of the desired complex, only numerous crystals of the title compound were found, which had probably formed through contact with moist air.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The positions of all H atoms were clearly identified in difference-Fourier syntheses. Hydrogen atoms attached to carbon atoms were refined with calculated positions (–CH3 = 0.98 Å, –CH2– = 0.99 Å, –CHarom– = 0.95 Å) and common Uiso(H) parameters for all hydrogen atoms of the DMPU molecule and one for each of the hydrogen atoms of the two phenyl groups. In order to obtain a realistic description of the hydrogen bond, the maximum electron density resulting from the X-ray data for the hydrogen atom was used to determine the direction of the O—H bond, while the position of the nucleus of the hydrogen atom was calculated using an O—H distance in better accordance with gas phase and neutron diffraction data. For this purpose, the position of the H atom of the hydroxyl group was refined with a fixed O—H distance of 0.96 Å before it was fixed and allowed to ride on the parent oxygen atom with a Uiso(H) parameter.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | [Sn(C6H5)2I(OH)]·2C6H12N2O |
| M r | 1089.95 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 100 |
| a, b, c (Å) | 10.1014 (4), 11.3064 (4), 17.1982 (7) |
| β (°) | 93.027 (2) |
| V (Å3) | 1961.47 (13) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 2.89 |
| Crystal size (mm) | 0.30 × 0.18 × 0.09 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.482, 0.671 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 100676, 4729, 4323 |
| R int | 0.079 |
| (sin θ/λ)max (Å−1) | 0.661 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.061, 1.05 |
| No. of reflections | 4729 |
| No. of parameters | 225 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.25, −1.47 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314625007114/zl4086sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314625007114/zl4086Isup2.hkl
CCDC reference: 2478813
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The Deutsche Forschungsgemeinschaft and the Government of Lower-Saxony are thanked for the funding of the diffractometer.
full crystallographic data
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Crystal data
| [Sn(C6H5)2I(OH)]·2C6H12N2O | F(000) = 1056 |
| Mr = 1089.95 | Dx = 1.845 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.1014 (4) Å | Cell parameters from 9764 reflections |
| b = 11.3064 (4) Å | θ = 2.7–29.2° |
| c = 17.1982 (7) Å | µ = 2.89 mm−1 |
| β = 93.027 (2)° | T = 100 K |
| V = 1961.47 (13) Å3 | Spat, colourless |
| Z = 2 | 0.30 × 0.18 × 0.09 mm |
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Data collection
| Bruker APEXII CCD diffractometer | 4323 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.079 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 28.0°, θmin = 2.7° |
| Tmin = 0.482, Tmax = 0.671 | h = −13→13 |
| 100676 measured reflections | k = −14→14 |
| 4729 independent reflections | l = −22→22 |
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Refinement
| Refinement on F2 | Hydrogen site location: mixed |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.0239P)2 + 3.8824P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.061 | (Δ/σ)max = 0.001 |
| S = 1.05 | Δρmax = 1.25 e Å−3 |
| 4729 reflections | Δρmin = −1.47 e Å−3 |
| 225 parameters | Extinction correction: SHELXL2014/7 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.00232 (17) |
| Primary atom site location: structure-invariant direct methods |
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Special details
| 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. |
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.04841 (2) | 0.35489 (2) | 0.49934 (2) | 0.01348 (6) | |
| C11 | 0.1816 (3) | 0.3343 (2) | 0.59931 (16) | 0.0228 (6) | |
| C12 | 0.1508 (4) | 0.3855 (4) | 0.66929 (19) | 0.0417 (8) | |
| H12 | 0.0736 | 0.4329 | 0.6721 | 0.063 (6)* | |
| C13 | 0.2341 (5) | 0.3668 (4) | 0.7360 (2) | 0.0582 (12) | |
| H13 | 0.2112 | 0.4003 | 0.7841 | 0.063 (6)* | |
| C14 | 0.3459 (5) | 0.3024 (4) | 0.7332 (3) | 0.0596 (13) | |
| H14 | 0.4016 | 0.2911 | 0.7788 | 0.063 (6)* | |
| C15 | 0.3787 (4) | 0.2530 (3) | 0.6634 (3) | 0.0536 (12) | |
| H15 | 0.4580 | 0.2082 | 0.6609 | 0.063 (6)* | |
| C16 | 0.2964 (3) | 0.2684 (3) | 0.5965 (2) | 0.0351 (7) | |
| H16 | 0.3193 | 0.2335 | 0.5488 | 0.063 (6)* | |
| C21 | −0.1222 (2) | 0.2451 (2) | 0.47739 (14) | 0.0156 (5) | |
| C22 | −0.2502 (3) | 0.2881 (3) | 0.48144 (17) | 0.0253 (6) | |
| H22 | −0.2645 | 0.3695 | 0.4917 | 0.031 (4)* | |
| C23 | −0.3580 (3) | 0.2115 (3) | 0.47049 (19) | 0.0325 (7) | |
| H23 | −0.4456 | 0.2413 | 0.4730 | 0.031 (4)* | |
| C24 | −0.3383 (3) | 0.0930 (3) | 0.45601 (16) | 0.0290 (6) | |
| H24 | −0.4121 | 0.0414 | 0.4489 | 0.031 (4)* | |
| C25 | −0.2116 (3) | 0.0499 (2) | 0.45184 (17) | 0.0260 (6) | |
| H25 | −0.1980 | −0.0318 | 0.4419 | 0.031 (4)* | |
| C26 | −0.1032 (3) | 0.1254 (2) | 0.46211 (16) | 0.0206 (5) | |
| H26 | −0.0159 | 0.0952 | 0.4587 | 0.031 (4)* | |
| I1 | 0.19964 (2) | 0.24368 (2) | 0.38647 (2) | 0.02578 (7) | |
| O1 | 0.06719 (18) | 0.51134 (15) | 0.44382 (11) | 0.0193 (4) | |
| H1 | 0.1273 | 0.5266 | 0.4036 | 0.048 (11)* | |
| O2 | 0.2304 (2) | 0.57144 (17) | 0.33999 (12) | 0.0253 (4) | |
| C1 | 0.2989 (3) | 0.5083 (2) | 0.29735 (15) | 0.0187 (5) | |
| N1 | 0.4246 (2) | 0.4779 (2) | 0.32074 (14) | 0.0227 (5) | |
| C2 | 0.5013 (3) | 0.3930 (3) | 0.27814 (19) | 0.0321 (7) | |
| H2A | 0.4822 | 0.3118 | 0.2960 | 0.049 (5)* | |
| H2B | 0.5972 | 0.4084 | 0.2882 | 0.049 (5)* | |
| C3 | 0.4654 (4) | 0.4039 (3) | 0.19181 (19) | 0.0406 (8) | |
| H3A | 0.4939 | 0.4820 | 0.1727 | 0.049 (5)* | |
| H3B | 0.5116 | 0.3419 | 0.1630 | 0.049 (5)* | |
| C4 | 0.3182 (4) | 0.3907 (3) | 0.17794 (18) | 0.0366 (8) | |
| H4A | 0.2932 | 0.4055 | 0.1224 | 0.049 (5)* | |
| H4B | 0.2915 | 0.3089 | 0.1906 | 0.049 (5)* | |
| N2 | 0.2502 (2) | 0.4741 (2) | 0.22624 (13) | 0.0240 (5) | |
| C5 | 0.4672 (3) | 0.5010 (3) | 0.40127 (19) | 0.0352 (7) | |
| H5A | 0.4406 | 0.5811 | 0.4156 | 0.047 (4)* | |
| H5B | 0.5639 | 0.4939 | 0.4075 | 0.047 (4)* | |
| H5C | 0.4260 | 0.4434 | 0.4351 | 0.047 (4)* | |
| C6 | 0.1125 (3) | 0.5007 (3) | 0.2053 (2) | 0.0370 (7) | |
| H6A | 0.0554 | 0.4447 | 0.2313 | 0.047 (4)* | |
| H6B | 0.0968 | 0.4938 | 0.1488 | 0.047 (4)* | |
| H6C | 0.0923 | 0.5814 | 0.2217 | 0.047 (4)* |
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.01511 (9) | 0.01051 (9) | 0.01513 (10) | −0.00128 (6) | 0.00380 (6) | −0.00111 (6) |
| C11 | 0.0244 (14) | 0.0204 (12) | 0.0231 (14) | −0.0079 (10) | −0.0037 (11) | 0.0057 (10) |
| C12 | 0.0402 (19) | 0.062 (2) | 0.0223 (16) | −0.0025 (17) | −0.0032 (14) | −0.0060 (15) |
| C13 | 0.069 (3) | 0.080 (3) | 0.0241 (18) | −0.018 (2) | −0.0147 (18) | 0.0021 (18) |
| C14 | 0.066 (3) | 0.057 (3) | 0.051 (3) | −0.022 (2) | −0.037 (2) | 0.026 (2) |
| C15 | 0.051 (2) | 0.037 (2) | 0.069 (3) | 0.0016 (16) | −0.031 (2) | 0.0154 (18) |
| C16 | 0.0325 (17) | 0.0232 (14) | 0.048 (2) | −0.0008 (12) | −0.0114 (15) | 0.0045 (13) |
| C21 | 0.0155 (11) | 0.0177 (12) | 0.0136 (11) | −0.0031 (9) | 0.0008 (9) | −0.0007 (9) |
| C22 | 0.0220 (13) | 0.0242 (14) | 0.0299 (15) | 0.0010 (11) | 0.0015 (11) | −0.0035 (11) |
| C23 | 0.0158 (13) | 0.0473 (19) | 0.0341 (17) | −0.0017 (13) | 0.0003 (12) | −0.0062 (14) |
| C24 | 0.0265 (14) | 0.0402 (17) | 0.0200 (14) | −0.0177 (13) | −0.0009 (11) | −0.0012 (12) |
| C25 | 0.0334 (15) | 0.0193 (13) | 0.0253 (14) | −0.0091 (11) | 0.0010 (11) | −0.0014 (11) |
| C26 | 0.0240 (13) | 0.0170 (12) | 0.0209 (13) | −0.0036 (10) | 0.0014 (10) | 0.0006 (10) |
| I1 | 0.02964 (11) | 0.01696 (10) | 0.03231 (12) | −0.00113 (7) | 0.01641 (8) | −0.00387 (7) |
| O1 | 0.0276 (10) | 0.0116 (8) | 0.0200 (9) | 0.0011 (7) | 0.0144 (7) | 0.0004 (7) |
| O2 | 0.0298 (10) | 0.0187 (9) | 0.0290 (10) | −0.0001 (8) | 0.0167 (8) | 0.0010 (8) |
| C1 | 0.0237 (13) | 0.0137 (11) | 0.0197 (13) | −0.0041 (10) | 0.0103 (10) | 0.0027 (9) |
| N1 | 0.0224 (11) | 0.0246 (11) | 0.0217 (11) | −0.0011 (9) | 0.0053 (9) | −0.0003 (9) |
| C2 | 0.0331 (16) | 0.0292 (15) | 0.0353 (17) | 0.0098 (13) | 0.0138 (13) | 0.0053 (13) |
| C3 | 0.058 (2) | 0.0357 (18) | 0.0309 (17) | 0.0173 (16) | 0.0256 (16) | 0.0019 (14) |
| C4 | 0.062 (2) | 0.0260 (15) | 0.0218 (15) | 0.0044 (15) | 0.0054 (14) | −0.0058 (12) |
| N2 | 0.0285 (12) | 0.0230 (11) | 0.0207 (11) | −0.0008 (9) | 0.0029 (9) | 0.0021 (9) |
| C5 | 0.0366 (17) | 0.0389 (18) | 0.0294 (16) | −0.0106 (14) | −0.0051 (13) | 0.0016 (13) |
| C6 | 0.0303 (16) | 0.0420 (18) | 0.0381 (18) | −0.0072 (14) | −0.0043 (13) | 0.0089 (14) |
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Geometric parameters (Å, º)
| Sn1—O1 | 2.024 (2) | C25—H25 | 0.9500 |
| Sn1—C11 | 2.139 (3) | C26—H26 | 0.9500 |
| Sn1—C21 | 2.141 (2) | O1—Sn1i | 2.174 (2) |
| Sn1—O1i | 2.174 (2) | O1—H1 | 0.9599 |
| Sn1—I1 | 2.8278 (2) | O2—C1 | 1.257 (3) |
| C11—C16 | 1.382 (4) | C1—N2 | 1.351 (4) |
| C11—C12 | 1.385 (5) | C1—N1 | 1.355 (3) |
| C12—C13 | 1.402 (5) | N1—C5 | 1.452 (4) |
| C12—H12 | 0.9500 | N1—C2 | 1.456 (4) |
| C13—C14 | 1.347 (7) | C2—C3 | 1.515 (5) |
| C13—H13 | 0.9500 | C2—H2A | 0.9900 |
| C14—C15 | 1.380 (7) | C2—H2B | 0.9900 |
| C14—H14 | 0.9500 | C3—C4 | 1.501 (5) |
| C15—C16 | 1.395 (5) | C3—H3A | 0.9900 |
| C15—H15 | 0.9500 | C3—H3B | 0.9900 |
| C16—H16 | 0.9500 | C4—N2 | 1.454 (4) |
| C21—C22 | 1.387 (4) | C4—H4A | 0.9900 |
| C21—C26 | 1.393 (3) | C4—H4B | 0.9900 |
| C22—C23 | 1.396 (4) | N2—C6 | 1.450 (4) |
| C22—H22 | 0.9500 | C5—H5A | 0.9800 |
| C23—C24 | 1.378 (5) | C5—H5B | 0.9800 |
| C23—H23 | 0.9500 | C5—H5C | 0.9800 |
| C24—C25 | 1.375 (4) | C6—H6A | 0.9800 |
| C24—H24 | 0.9500 | C6—H6B | 0.9800 |
| C25—C26 | 1.393 (4) | C6—H6C | 0.9800 |
| O1—Sn1—C11 | 113.80 (9) | C25—C26—H26 | 119.9 |
| O1—Sn1—C21 | 121.22 (9) | C21—C26—H26 | 119.9 |
| C11—Sn1—C21 | 123.01 (10) | Sn1—O1—Sn1i | 109.26 (8) |
| O1—Sn1—O1i | 70.74 (8) | Sn1—O1—H1 | 125.2 |
| C11—Sn1—O1i | 92.52 (10) | Sn1i—O1—H1 | 125.0 |
| C21—Sn1—O1i | 92.09 (8) | O2—C1—N2 | 120.4 (3) |
| O1—Sn1—I1 | 89.84 (5) | O2—C1—N1 | 120.4 (3) |
| C11—Sn1—I1 | 99.43 (8) | N2—C1—N1 | 119.1 (2) |
| C21—Sn1—I1 | 94.58 (7) | C1—N1—C5 | 117.6 (2) |
| O1i—Sn1—I1 | 160.12 (5) | C1—N1—C2 | 122.2 (2) |
| C16—C11—C12 | 118.9 (3) | C5—N1—C2 | 117.3 (3) |
| C16—C11—Sn1 | 121.6 (2) | N1—C2—C3 | 109.5 (2) |
| C12—C11—Sn1 | 119.5 (2) | N1—C2—H2A | 109.8 |
| C11—C12—C13 | 119.7 (4) | C3—C2—H2A | 109.8 |
| C11—C12—H12 | 120.2 | N1—C2—H2B | 109.8 |
| C13—C12—H12 | 120.2 | C3—C2—H2B | 109.8 |
| C14—C13—C12 | 121.3 (4) | H2A—C2—H2B | 108.2 |
| C14—C13—H13 | 119.3 | C4—C3—C2 | 109.4 (3) |
| C12—C13—H13 | 119.3 | C4—C3—H3A | 109.8 |
| C13—C14—C15 | 119.4 (3) | C2—C3—H3A | 109.8 |
| C13—C14—H14 | 120.3 | C4—C3—H3B | 109.8 |
| C15—C14—H14 | 120.3 | C2—C3—H3B | 109.8 |
| C14—C15—C16 | 120.4 (4) | H3A—C3—H3B | 108.2 |
| C14—C15—H15 | 119.8 | N2—C4—C3 | 109.8 (3) |
| C16—C15—H15 | 119.8 | N2—C4—H4A | 109.7 |
| C11—C16—C15 | 120.2 (4) | C3—C4—H4A | 109.7 |
| C11—C16—H16 | 119.9 | N2—C4—H4B | 109.7 |
| C15—C16—H16 | 119.9 | C3—C4—H4B | 109.7 |
| C22—C21—C26 | 119.2 (2) | H4A—C4—H4B | 108.2 |
| C22—C21—Sn1 | 122.11 (19) | C1—N2—C6 | 117.7 (3) |
| C26—C21—Sn1 | 118.62 (19) | C1—N2—C4 | 122.9 (2) |
| C21—C22—C23 | 119.9 (3) | C6—N2—C4 | 118.0 (3) |
| C21—C22—H22 | 120.1 | N1—C5—H5A | 109.5 |
| C23—C22—H22 | 120.1 | N1—C5—H5B | 109.5 |
| C24—C23—C22 | 120.5 (3) | H5A—C5—H5B | 109.5 |
| C24—C23—H23 | 119.7 | N1—C5—H5C | 109.5 |
| C22—C23—H23 | 119.7 | H5A—C5—H5C | 109.5 |
| C25—C24—C23 | 119.8 (3) | H5B—C5—H5C | 109.5 |
| C25—C24—H24 | 120.1 | N2—C6—H6A | 109.5 |
| C23—C24—H24 | 120.1 | N2—C6—H6B | 109.5 |
| C24—C25—C26 | 120.2 (3) | H6A—C6—H6B | 109.5 |
| C24—C25—H25 | 119.9 | N2—C6—H6C | 109.5 |
| C26—C25—H25 | 119.9 | H6A—C6—H6C | 109.5 |
| C25—C26—C21 | 120.3 (3) | H6B—C6—H6C | 109.5 |
| C16—C11—C12—C13 | −1.8 (5) | Sn1—C21—C26—C25 | 176.4 (2) |
| Sn1—C11—C12—C13 | 176.5 (3) | O2—C1—N1—C5 | 11.5 (4) |
| C11—C12—C13—C14 | 1.7 (6) | N2—C1—N1—C5 | −171.3 (2) |
| C12—C13—C14—C15 | −0.5 (7) | O2—C1—N1—C2 | 172.0 (2) |
| C13—C14—C15—C16 | −0.7 (6) | N2—C1—N1—C2 | −10.8 (4) |
| C12—C11—C16—C15 | 0.6 (5) | C1—N1—C2—C3 | 34.0 (4) |
| Sn1—C11—C16—C15 | −177.6 (3) | C5—N1—C2—C3 | −165.5 (3) |
| C14—C15—C16—C11 | 0.6 (6) | N1—C2—C3—C4 | −54.7 (4) |
| C26—C21—C22—C23 | 0.2 (4) | C2—C3—C4—N2 | 53.8 (3) |
| Sn1—C21—C22—C23 | −176.8 (2) | O2—C1—N2—C6 | −7.2 (4) |
| C21—C22—C23—C24 | 0.3 (5) | N1—C1—N2—C6 | 175.6 (2) |
| C22—C23—C24—C25 | −0.4 (5) | O2—C1—N2—C4 | −173.0 (3) |
| C23—C24—C25—C26 | −0.1 (4) | N1—C1—N2—C4 | 9.8 (4) |
| C24—C25—C26—C21 | 0.6 (4) | C3—C4—N2—C1 | −32.4 (4) |
| C22—C21—C26—C25 | −0.6 (4) | C3—C4—N2—C6 | 161.8 (3) |
Symmetry code: (i) −x, −y+1, −z+1.
Di-µ-hydroxido-bis[iodidodiphenyltin(IV)]–1,3-dimethylimidazolidin-2-one (1/2). Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2 | 0.96 | 1.63 | 2.584 (3) | 172 |
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314625007114/zl4086sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314625007114/zl4086Isup2.hkl
CCDC reference: 2478813
Additional supporting information: crystallographic information; 3D view; checkCIF report