research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Crystal structure of μ-oxalato-κ2O1:O2-bis­­[(di­methyl sulfoxide-κO)tri­phenyl­tin(IV)]

aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, bUniversita di Padova, Dipartimento di Scienze del Farmaco RMXS, Laboratorio di Radiofarmacia, Modellistica Molecolare e Diffrattometria a Raggi X, Via Francesco Marzolo 5, 35131, Padova, Italy, and cInstituto de Física, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico
*Correspondence e-mail: sgne0281@yahoo.fr

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 24 May 2017; accepted 7 June 2017; online 13 June 2017)

In the previously reported [C2O4(SnPh3)2] complex [Diop et al. (2003[Diop, L., Mahieu, B., Mahon, M. F., Molloy, K. C. & Okio, K. Y. A. (2003). Appl. Organomet. Chem. 17, 881-882.]). Appl. Organomet. Chem. 17, 881–882.], the SnIV atoms are able to formally complete their coordination by addition of dimethyl sulfoxide (DMSO) mol­ecules provided by the reaction medium, affording the title complex, [Sn2(C6H5)6(C2O4)(C2H6OS)2]. The SnIV atoms are then penta­coordinated, with a common trans trigonal–bipyramidal arrangement. The asymmetric unit contains one half-mol­ecule, which is completed by inversion symmetry in space group type C2/c. The inversion centre is placed at the mid-point of the central bis-monodentate oxalate dianion, C2O42−, which bridges the [(SnPh3)(DMSO)] moieties. The mol­ecule crystallizes as a disordered system, with two phenyl rings disordered by rotation about their Sn—C bonds, while the DMSO mol­ecule is split over two positions due to a tetra­hedral inversion at the S atom. All disordered parts were refined with occupancies fixed of 0.5.

1. Chemical context

One of the values of SnIV coordination chemistry is related to the ambiguous valency of this main element, for which a plethora of tetra- and penta­coordinated compounds have been described. This makes a difference with C and Si compounds, based almost exclusively on tetra­valent nodes, with very few cases of hypervalency. For Sn mononuclear compounds, a survey of the current Cambridge database (CSD V5.38 updated February 2017; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) shows that coordination number four is more represented than coordination number five, with distributions of 63 and 37%, respectively, for the ca 4700 structures deposited to date. Stable compounds with a coordination number of four for the SnIV atom are thus attractive starting materials for the chemistry of SnIV complexes with a coordination number of five, including polynuclear species, which have no equivalent with the other elements of group 14. Tri­phenyl­tin chloride, SnPh3Cl, is one of these well used mol­ecules, with the additional advantage that the Cl atom may behave as a leaving group, while the SnPh3 fragment is a stable core structure.

The here reported dinuclear compound is a continuation of previous works carried out by the Dakar group about the synthesis of Sn2 complexes using the oxalate dianion as a bridging ligand. The simplest member of this family is [C2O4(SnPh3)2], where both Sn sites exhibit coordination number four (Diop et al., 2003[Diop, L., Mahieu, B., Mahon, M. F., Molloy, K. C. & Okio, K. Y. A. (2003). Appl. Organomet. Chem. 17, 881-882.]). However, it seems that whenever possible, the fifth coordination site in such complexes is occupied by a Lewis base, for example if the reaction is realized in a donor solvent such as H2O, DMF, thio­urea, etc. In this context, the structures of {C2O4[(SnMe3)(H2O)]2}, {C2O4[(SnPh3)(DMF)]2} and {C2O4[(SnPh3)(thio­urea)]2} have been described (Diop et al., 1997[Diop, L., Mahon, M. F., Molloy, K. C. & Sidibe, M. (1997). Main Group Met. Chem. 20, 649-654.]; Gueye et al., 2011[Gueye, N., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2011). Main Group Met. Chem. 34, 3-4.]; Sow et al., 2012[Sow, Y., Diop, L., Molloy, K. C. & Kociok-Kohn, G. (2012). Acta Cryst. E68, m1337.]). In this dynamic, we now report a new complex synthesized using a mixture of dimethyl sulfoxide (DMSO) and methanol as solvent. The former component of this mixture is clearly a more stabilizing ligand for Sn atoms, resulting in the crystallization of the title compound, {C2O4[(SnPh3)(DMSO)]2}. Inter­estingly, the complex [(DMSO)SnPh3] is known (Kumar et al., 2009[Kumar, S., Shadab, S. M. & Idrees, M. (2009). Acta Cryst. E65, m1602-m1603.]), but was not detected in this reaction, indicating that the oxalate-bridged species is probably formed prior to solvent coordination.

[Scheme 1]

2. Structural commentary

As expected, the oxalate dianion behaves as a bis-monodentate μ2-bridging ligand for two [SnPh3(DMSO)] moieties. The resulting neutral dinuclear complex is situated on a crystallographic inversion centre, placed at the midpoint of the C—C bond of the oxalate bridge (Fig. 1[link]). Although that symmetry is consistent with the mol­ecular symmetry, the mol­ecule is strongly disordered: two of the three phenyl rings in the asymmetric unit are disordered over two positions by rotation about their Sn—C bonds, and the DMSO mol­ecule is also disordered over two positions, as a consequence of an inversion at the tetra­hedral S atom.

[Figure 1]
Figure 1
The mol­ecular structure of the title complex, with displacement ellipsoids at the 30% probability level. For phenyl rings C8–C13 and C14–C19 and for the DMSO mol­ecule, only disordered part A (occupancy 0.5) is represented, and all H atoms are omitted. Unlabelled atoms are generated by the symmetry operation ([{3\over 2}] − x, [{1\over 2}] − y, 2 − z).

The SnIV atom is penta­coordinated in a common trans trigonal–bipyramidal manner, the phenyl groups being in equatorial positions, while the coordinating O atoms from the oxalate and DMSO ligands occupy the apical sites. The three Sn—C bonds are similar in length to those already reported for related complexes including the SnPh3 fragment (Sow et al., 2012[Sow, Y., Diop, L., Molloy, K. C. & Kociok-Kohn, G. (2012). Acta Cryst. E68, m1337.]; Gueye et al., 2011[Gueye, N., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2011). Main Group Met. Chem. 34, 3-4.]), while the Sn—O bond for the oxalate is rather short, 2.147 (2) Å, compared to that found in {C2O4[(SnMe3)(H2O)]2}, 2.209 Å, or in the anionic polymer [(CH3)3S]n[C2O4SnPh3]n (2.220 Å; Ng et al., 1994[Ng, S. W., Kumar Das, V. G., Luo, B.-S. & Mak, T. C. W. (1994). Z. Kristallogr. 209, 882-884.]). This tight bonding character for the bridging oxalate may be related to its planar conformation, imposed by symmetry. The staggered arrangement for the six phenyl rings, also imposed by symmetry, avoids any steric hindrance in the complex. The apical DMSO mol­ecule has an Sn—O bond length of 2.354 (6)–2.403 (6) Å, reflecting a less pronounced coordination strength.

3. Supra­molecular features

These discrete binuclear mol­ecules inter­act through van der Waals forces in the crystal, and no strong inter­actions are observed. The carbonyl groups of the oxalate dianion, C1—O1 and C1=O2, are the unique potential acceptor groups for hydrogen bonding, and indeed, weak inter­molecular C—H⋯O contacts are formed (Table 1[link]): two mol­ecules related by a glide plane are oriented almost perpendicular, in such a way that methyl groups of the terminal DMSO ligands in one mol­ecule form C—H⋯O contacts with the oxalate bridge of the other mol­ecule (Fig. 2[link]). These contacts are favoured by the disorder affecting the DMSO ligands, and allow to pack the complexes densely in the crystal, even in the absence of any ππ contacts between the phenyl rings.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C20A—H20A⋯O2i 0.96 2.51 3.43 (4) 162
C21A—H21A⋯O2i 0.96 2.60 3.49 (2) 154
C21B—H21D⋯O1ii 0.96 2.36 3.278 (19) 160
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 2]
Figure 2
Part of the crystal structure viewed down reciprocal axis a*. For disordered phenyl rings, only one orientation is retained, while both disordered parts for the DMSO mol­ecules are represented, in green and magenta (parts A and B, respectively). Inter­molecular C—H⋯O contacts listed in Table 1[link] are represented for the central mol­ecule as blue dashed lines.

4. Database survey

According to the Cambridge Structural Database (CSD V5.38 updated February 2017; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]), eleven structures containing a bis-monodentate bridging μ2-oxalate linked to two Sn atoms have been characterized by X-ray diffraction. In addition to those already mentioned in the previous sections, a cis [C2O4(SnR3)2] complex with bulky R groups has been reported (Tan et al., 2014[Tan, Y.-X., Feng, Y.-L., Yin, D.-L., Yu, J.-X., Jiang, W.-J., Zhang, F.-X. & Kuang, D.-Z. (2014). Chin. J. Inorg. Chem. 30, 2781-2788.]), as well as stannate complexes (Sow et al., 2011[Sow, Y., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2011). Main Group Met. Chem. 34, 127-130.]; Ng & Kumar Das, 1990[Ng, S. W. & Kumar Das, V. G. (1990). J. Organomet. Chem. 390, 19-28.], 1993[Ng, S. W. & Kumar Das, V. G. (1993). J. Organomet. Chem. 456, 175-179.]; Kruger et al., 1976[Kruger, G. J., Breet, E. L. J. & Van Eldik, R. (1976). Inorg. Chim. Acta, 19, 151-157.]). Among these structures, the trans coordination mode for the oxalate bridge dominates. The oxalate dianion is, however, known for having a very rich coordination behaviour, and the μ2-κ2-O,O′ coordination mode observed in the title compound is not the most common. Limiting the survey to Sn compounds, the chelating bis-bidentate bridging mode is more represented (i.e. polynuclear complexes including the μ2-oxalato-κ4O1,O2:O1′,O2′ bridge). In that case, the conformation of the bridge is invariably planar, while the μ2-κ2-O,O′ bridge may be planar or twisted.

5. Synthesis and crystallization

[CH3NH2(CH2)2NH2CH3]C2O4 (L) was obtained as a powder, on mixing the di­amine CH3NH(CH2)2NHCH3 with C2O4H2·2H2O in a 1:1 ratio (v/v) in water, and allowing the water to evaporate at 333 K. When 0.10 g (0.26 mmol) of SnPh3Cl in 15 ml of a 1:1 ratio (v/v) DMSO/methanol mixture was reacted with 0.06 g (0.26 mmol) of L, a clear solution was obtained. Slow solvent evaporation over two weeks afforded a powder, which was collected. This powder dissolved in aceto­nitrile gave a slightly cloudy solution, which was quickly filtered off. The resulting clear solution, when allowed to evaporate slowly, afforded, six months after, colourless crystals of the title complex suitable for X-ray diffraction.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The mol­ecular structure is strongly disordered. Three different data sets were collected for three different crystals, on different diffractometers; however, all gave the same disordered structure. In the asymmetric unit, two of the three phenyl rings are disordered over two positions: rings C8–C13 and C14–C19 were split over sites A and B. Attempts to refine site occupancies for the disordered parts resulted in free variables converging to values very close to 1/2 [maximum deviation for DMSO: 0.477 (5) and 0.523 (5)] with no clear improvement for the involved displacement parameters.

Table 2
Experimental details

Crystal data
Chemical formula [Sn2(C6H5)6(C2O4)(C2H6OS)2]
Mr 944.25
Crystal system, space group Monoclinic, C2/c
Temperature (K) 297
a, b, c (Å) 15.4638 (14), 16.2069 (10), 17.6205 (15)
β (°) 111.213 (10)
V3) 4116.8 (6)
Z 4
Radiation type Mo Kα
μ (mm−1) 1.36
Crystal size (mm) 0.19 × 0.18 × 0.11
 
Data collection
Diffractometer Agilent Xcalibur Atlas Gemini
Absorption correction Gaussian (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.])
Tmin, Tmax 0.955, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections 27591, 5762, 3476
Rint 0.064
(sin θ/λ)max−1) 0.694
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.090, 1.02
No. of reflections 5762
No. of parameters 383
No. of restraints 180
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.50, −0.53
Computer programs: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

The four rings were restrained to be flat with standard deviation of 0.02 Å3, and the C atoms in a given ring were restrained to have the same anisotropic components, within a standard deviation of 0.04 Å2. Finally, A and B rings for each disordered phenyl group were restrained to have the same geometry (standard deviations: 0.02 Å for C C bond lengths and 0.04 Å for 1,3-distances). The DMSO mol­ecule is also disordered over two positions, labelled A and B, with occupancies fixed to 0.5. These parts were refined freely.

Supporting information


Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

µ-Oxalato-κ2O1:O2-bis[triphenyl(dimethyl sulfoxide-κO)tin(IV)] top
Crystal data top
[Sn2(C6H5)6(C2O4)(C2H6OS)2]F(000) = 1896
Mr = 944.25Dx = 1.523 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 15.4638 (14) ÅCell parameters from 5828 reflections
b = 16.2069 (10) Åθ = 3.5–25.5°
c = 17.6205 (15) ŵ = 1.36 mm1
β = 111.213 (10)°T = 297 K
V = 4116.8 (6) Å3Block, colourless
Z = 40.19 × 0.18 × 0.11 mm
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer
5762 independent reflections
Radiation source: Enhance (Mo) X-ray Source3476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
Detector resolution: 10.5564 pixels mm-1θmax = 29.6°, θmin = 3.0°
ω scansh = 2120
Absorption correction: gaussian
(CrysAlis PRO; Agilent, 2013)
k = 2022
Tmin = 0.955, Tmax = 0.978l = 2324
27591 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0254P)2 + 2.4676P]
where P = (Fo2 + 2Fc2)/3
5762 reflections(Δ/σ)max = 0.001
383 parametersΔρmax = 0.50 e Å3
180 restraintsΔρmin = 0.53 e Å3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn0.74863 (2)0.38396 (2)0.82897 (2)0.05437 (10)
O10.73200 (18)0.28181 (13)0.90012 (13)0.0554 (6)
O20.81455 (18)0.34129 (15)1.01798 (14)0.0627 (7)
C10.7646 (2)0.2865 (2)0.9783 (2)0.0454 (8)
C20.8950 (3)0.3837 (2)0.8639 (2)0.0558 (9)
C30.9412 (3)0.3172 (3)0.8478 (3)0.0744 (12)
H3A0.9081580.2698720.8246460.089*
C41.0369 (4)0.3197 (4)0.8656 (3)0.0940 (15)
H4A1.0671760.2741250.8549090.113*
C51.0860 (4)0.3893 (4)0.8988 (3)0.1056 (19)
H5A1.1495650.3912810.9102450.127*
C61.0420 (4)0.4552 (4)0.9148 (3)0.1067 (18)
H6A1.0756120.5021640.9382340.128*
C70.9470 (3)0.4532 (3)0.8967 (3)0.0811 (13)
H7A0.9175430.4996300.9067520.097*
C8A0.6690 (7)0.3048 (6)0.7188 (8)0.041 (3)0.5
C9A0.5839 (5)0.2732 (4)0.7073 (4)0.060 (2)0.5
H9AA0.5583000.2826280.7467990.072*0.5
C10A0.5333 (6)0.2272 (5)0.6388 (5)0.072 (2)0.5
H10A0.4751260.2064300.6329410.087*0.5
C11A0.5698 (11)0.2132 (8)0.5811 (8)0.073 (4)0.5
H11A0.5364870.1828460.5349590.088*0.5
C12A0.6553 (12)0.2434 (11)0.5901 (11)0.081 (5)0.5
H12A0.6804930.2328110.5505340.097*0.5
C13A0.7046 (10)0.2895 (10)0.6578 (11)0.069 (5)0.5
H13A0.7622680.3107410.6628660.083*0.5
C8B0.6772 (8)0.3329 (6)0.7227 (8)0.045 (3)0.5
C9B0.5824 (6)0.3406 (6)0.6914 (4)0.074 (2)0.5
H9BA0.5545400.3750350.7181100.089*0.5
C10B0.5261 (7)0.2996 (7)0.6223 (5)0.100 (3)0.5
H10B0.4621790.3069210.6032360.120*0.5
C11B0.5651 (13)0.2487 (8)0.5825 (9)0.098 (5)0.5
H11B0.5277470.2206700.5362460.118*0.5
C12B0.6595 (13)0.2385 (12)0.6105 (11)0.089 (6)0.5
H12B0.6864150.2037450.5832030.107*0.5
C13B0.7142 (11)0.2802 (10)0.6793 (11)0.066 (5)0.5
H13B0.7782030.2730770.6976460.079*0.5
C14A0.6762 (6)0.4614 (6)0.8894 (5)0.051 (3)0.5
C15A0.6973 (8)0.5429 (6)0.9128 (5)0.069 (3)0.5
H15A0.7476120.5681060.9052810.083*0.5
C16A0.6444 (9)0.5870 (10)0.9473 (7)0.097 (6)0.5
H16A0.6589090.6417410.9625740.116*0.5
C17A0.5707 (8)0.5503 (8)0.9590 (6)0.117 (4)0.5
H17A0.5360180.5800730.9830540.141*0.5
C18A0.5470 (6)0.4700 (7)0.9358 (5)0.099 (3)0.5
H18A0.4958290.4458200.9427940.118*0.5
C19A0.6004 (5)0.4259 (5)0.9020 (4)0.065 (2)0.5
H19A0.5855130.3710910.8873100.078*0.5
C14B0.6686 (6)0.4733 (6)0.8548 (5)0.048 (2)0.5
C15B0.6971 (7)0.5049 (6)0.9333 (6)0.066 (3)0.5
H15B0.7503680.4843170.9731730.079*0.5
C16B0.6469 (10)0.5669 (8)0.9528 (10)0.098 (7)0.5
H16B0.6663470.5876801.0055480.117*0.5
C17B0.5690 (8)0.5971 (5)0.8944 (8)0.093 (3)0.5
H17B0.5353290.6389070.9072650.111*0.5
C18B0.5398 (6)0.5661 (6)0.8164 (6)0.095 (3)0.5
H18B0.4863500.5870470.7770860.114*0.5
C19B0.5887 (5)0.5041 (5)0.7957 (5)0.066 (2)0.5
H19B0.5684700.4834320.7429120.079*0.5
S1A0.7716 (2)0.52338 (16)0.68682 (18)0.0811 (8)0.5
O3A0.7554 (4)0.5126 (4)0.7693 (4)0.0732 (16)0.5
C20A0.865 (2)0.575 (3)0.708 (3)0.137 (14)0.5
H20A0.8644840.6048340.6608650.205*0.5
H20B0.9173450.5383920.7257170.205*0.5
H20C0.8700350.6135860.7511150.205*0.5
C21A0.6862 (16)0.5830 (16)0.6302 (14)0.184 (13)0.5
H21A0.7012700.6051390.5859780.276*0.5
H21B0.6773250.6273450.6627220.276*0.5
H21C0.6301970.5511180.6088570.276*0.5
S1B0.76364 (17)0.56427 (15)0.72611 (17)0.0723 (6)0.5
O3B0.7508 (4)0.4700 (3)0.7186 (4)0.0728 (17)0.5
C20B0.8649 (16)0.597 (3)0.710 (3)0.096 (7)0.5
H20D0.8610310.6554180.6994200.144*0.5
H20E0.8702860.5681540.6647300.144*0.5
H20F0.9182800.5859650.7581070.144*0.5
C21B0.6869 (12)0.6082 (12)0.6425 (14)0.101 (6)0.5
H21D0.7042560.6644910.6390610.152*0.5
H21E0.6261770.6064390.6456340.152*0.5
H21F0.6862670.5786280.5951140.152*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.05831 (17)0.05370 (17)0.05635 (17)0.00491 (13)0.02705 (13)0.01576 (12)
O10.0847 (18)0.0497 (14)0.0311 (13)0.0065 (12)0.0201 (12)0.0076 (10)
O20.0827 (19)0.0523 (15)0.0485 (15)0.0168 (14)0.0183 (14)0.0011 (12)
C10.055 (2)0.0419 (19)0.041 (2)0.0038 (17)0.0200 (17)0.0037 (15)
C20.055 (2)0.072 (3)0.043 (2)0.002 (2)0.0201 (17)0.0074 (18)
C30.064 (3)0.084 (3)0.075 (3)0.002 (2)0.024 (2)0.000 (2)
C40.074 (4)0.125 (5)0.091 (4)0.017 (3)0.040 (3)0.001 (3)
C50.063 (3)0.174 (6)0.083 (4)0.025 (4)0.030 (3)0.021 (4)
C60.088 (4)0.145 (5)0.079 (4)0.042 (4)0.021 (3)0.023 (3)
C70.079 (3)0.095 (4)0.067 (3)0.009 (3)0.024 (2)0.012 (2)
C8A0.054 (6)0.033 (6)0.032 (4)0.004 (4)0.011 (4)0.007 (4)
C9A0.063 (5)0.063 (5)0.053 (5)0.008 (4)0.021 (4)0.004 (4)
C10A0.071 (6)0.078 (6)0.064 (6)0.026 (5)0.021 (5)0.005 (5)
C11A0.085 (8)0.074 (8)0.052 (6)0.020 (6)0.014 (6)0.001 (5)
C12A0.126 (13)0.083 (10)0.046 (7)0.007 (9)0.045 (8)0.006 (6)
C13A0.072 (9)0.075 (9)0.073 (11)0.019 (7)0.041 (8)0.004 (7)
C8B0.053 (6)0.047 (8)0.037 (5)0.005 (5)0.020 (4)0.007 (5)
C9B0.061 (6)0.113 (7)0.047 (5)0.006 (6)0.017 (4)0.014 (5)
C10B0.062 (6)0.169 (11)0.060 (6)0.019 (7)0.010 (5)0.025 (7)
C11B0.108 (11)0.125 (14)0.052 (7)0.027 (10)0.016 (7)0.023 (8)
C12B0.117 (13)0.085 (11)0.068 (11)0.013 (9)0.036 (8)0.011 (8)
C13B0.070 (8)0.065 (8)0.057 (8)0.021 (6)0.018 (6)0.005 (6)
C14A0.059 (5)0.056 (6)0.032 (5)0.002 (4)0.010 (5)0.002 (5)
C15A0.074 (6)0.061 (7)0.063 (7)0.021 (6)0.013 (5)0.008 (5)
C16A0.100 (14)0.082 (9)0.100 (12)0.022 (8)0.026 (11)0.038 (8)
C17A0.095 (9)0.155 (12)0.091 (8)0.038 (9)0.020 (7)0.045 (8)
C18A0.074 (6)0.152 (10)0.076 (6)0.008 (7)0.035 (5)0.012 (6)
C19A0.065 (5)0.084 (6)0.051 (5)0.003 (4)0.027 (4)0.005 (4)
C14B0.053 (5)0.049 (5)0.045 (6)0.001 (4)0.021 (5)0.003 (4)
C15B0.067 (6)0.060 (7)0.065 (7)0.023 (6)0.018 (5)0.013 (6)
C16B0.101 (14)0.073 (9)0.106 (12)0.022 (8)0.021 (10)0.020 (7)
C17B0.091 (8)0.071 (7)0.130 (10)0.022 (6)0.057 (8)0.004 (6)
C18B0.064 (6)0.100 (8)0.111 (8)0.028 (5)0.019 (6)0.021 (6)
C19B0.058 (5)0.078 (6)0.059 (5)0.006 (4)0.019 (4)0.004 (4)
S1A0.110 (2)0.0488 (14)0.107 (2)0.0064 (13)0.0655 (18)0.0066 (14)
O3A0.103 (5)0.057 (4)0.069 (4)0.005 (3)0.043 (4)0.021 (3)
C20A0.125 (19)0.15 (3)0.152 (19)0.008 (14)0.076 (15)0.07 (2)
C21A0.128 (16)0.27 (3)0.093 (12)0.073 (16)0.037 (10)0.093 (16)
S1B0.0840 (17)0.0567 (14)0.0848 (18)0.0119 (12)0.0407 (14)0.0040 (13)
O3B0.108 (5)0.039 (3)0.084 (5)0.010 (3)0.050 (4)0.010 (3)
C20B0.045 (9)0.110 (13)0.125 (14)0.016 (7)0.021 (8)0.059 (11)
C21B0.080 (10)0.080 (7)0.171 (17)0.044 (7)0.079 (11)0.071 (9)
Geometric parameters (Å, º) top
Sn—C8B1.979 (13)C12B—H12B0.9300
Sn—C14B2.060 (10)C13B—H13B0.9300
Sn—C22.120 (4)C14A—C15A1.387 (11)
Sn—O12.147 (2)C14A—C19A1.394 (10)
Sn—C14A2.196 (10)C15A—C16A1.383 (12)
Sn—C8A2.281 (12)C15A—H15A0.9300
Sn—O3A2.354 (6)C16A—C17A1.366 (15)
Sn—O3B2.403 (6)C16A—H16A0.9300
O1—C11.286 (4)C17A—C18A1.373 (12)
O2—C11.218 (4)C17A—H17A0.9300
C1—C1i1.562 (6)C18A—C19A1.381 (10)
C2—C31.379 (5)C18A—H18A0.9300
C2—C71.382 (6)C19A—H19A0.9300
C3—C41.398 (6)C14B—C19B1.388 (10)
C3—H3A0.9300C14B—C15B1.389 (11)
C4—C51.367 (7)C15B—C16B1.387 (12)
C4—H4A0.9300C15B—H15B0.9300
C5—C61.350 (7)C16B—C17B1.361 (14)
C5—H5A0.9300C16B—H16B0.9300
C6—C71.386 (6)C17B—C18B1.378 (12)
C6—H6A0.9300C17B—H17B0.9300
C7—H7A0.9300C18B—C19B1.384 (10)
C8A—C9A1.357 (11)C18B—H18B0.9300
C8A—C13A1.395 (12)C19B—H19B0.9300
C9A—C10A1.394 (9)S1A—O3A1.572 (6)
C9A—H9AA0.9300S1A—C20A1.60 (3)
C10A—C11A1.348 (12)S1A—C21A1.65 (2)
C10A—H10A0.9300C20A—H20A0.9600
C11A—C12A1.365 (13)C20A—H20B0.9600
C11A—H11A0.9300C20A—H20C0.9600
C12A—C13A1.380 (12)C21A—H21A0.9600
C12A—H12A0.9300C21A—H21B0.9600
C13A—H13A0.9300C21A—H21C0.9600
C8B—C9B1.372 (11)S1B—O3B1.540 (6)
C8B—C13B1.399 (11)S1B—C21B1.679 (19)
C9B—C10B1.384 (10)S1B—C20B1.77 (3)
C9B—H9BA0.9300C20B—H20D0.9600
C10B—C11B1.357 (13)C20B—H20E0.9600
C10B—H10B0.9300C20B—H20F0.9600
C11B—C12B1.371 (13)C21B—H21D0.9600
C11B—H11B0.9300C21B—H21E0.9600
C12B—C13B1.379 (12)C21B—H21F0.9600
C8B—Sn—C2116.5 (4)C8B—C13B—H13B118.7
C14B—Sn—C2126.9 (3)C15A—C14A—C19A117.8 (9)
C8B—Sn—O194.9 (3)C15A—C14A—Sn125.6 (7)
C14B—Sn—O1101.8 (2)C19A—C14A—Sn116.6 (7)
C2—Sn—O199.80 (12)C16A—C15A—C14A120.7 (11)
C2—Sn—C14A122.6 (3)C16A—C15A—H15A119.6
O1—Sn—C14A88.1 (2)C14A—C15A—H15A119.6
C2—Sn—C8A115.9 (3)C17A—C16A—C15A119.9 (13)
O1—Sn—C8A85.5 (3)C17A—C16A—H16A120.0
C2—Sn—O3A85.17 (18)C15A—C16A—H16A120.0
O1—Sn—O3A167.81 (17)C16A—C17A—C18A121.1 (11)
C2—Sn—O3B84.84 (18)C16A—C17A—H17A119.5
O1—Sn—O3B163.62 (16)C18A—C17A—H17A119.5
C1—O1—Sn119.8 (2)C17A—C18A—C19A118.8 (9)
O2—C1—O1125.4 (3)C17A—C18A—H18A120.6
O2—C1—C1i120.4 (4)C19A—C18A—H18A120.6
O1—C1—C1i114.2 (4)C18A—C19A—C14A121.6 (9)
C3—C2—C7117.2 (4)C18A—C19A—H19A119.2
C3—C2—Sn121.3 (3)C14A—C19A—H19A119.2
C7—C2—Sn121.2 (3)C19B—C14B—C15B119.3 (9)
C2—C3—C4121.1 (4)C19B—C14B—Sn122.0 (6)
C2—C3—H3A119.5C15B—C14B—Sn118.7 (7)
C4—C3—H3A119.5C16B—C15B—C14B120.6 (10)
C5—C4—C3119.9 (5)C16B—C15B—H15B119.7
C5—C4—H4A120.0C14B—C15B—H15B119.7
C3—C4—H4A120.0C17B—C16B—C15B119.7 (12)
C6—C5—C4119.9 (5)C17B—C16B—H16B120.2
C6—C5—H5A120.1C15B—C16B—H16B120.2
C4—C5—H5A120.1C16B—C17B—C18B120.2 (10)
C5—C6—C7120.3 (5)C16B—C17B—H17B119.9
C5—C6—H6A119.8C18B—C17B—H17B119.9
C7—C6—H6A119.8C17B—C18B—C19B121.1 (8)
C2—C7—C6121.6 (5)C17B—C18B—H18B119.5
C2—C7—H7A119.2C19B—C18B—H18B119.5
C6—C7—H7A119.2C18B—C19B—C14B119.1 (8)
C9A—C8A—C13A116.7 (10)C18B—C19B—H19B120.5
C9A—C8A—Sn122.4 (9)C14B—C19B—H19B120.5
C13A—C8A—Sn120.9 (9)O3A—S1A—C20A105.9 (18)
C8A—C9A—C10A122.8 (9)O3A—S1A—C21A105.3 (9)
C8A—C9A—H9AA118.6C20A—S1A—C21A107.1 (17)
C10A—C9A—H9AA118.6S1A—O3A—Sn124.0 (4)
C11A—C10A—C9A119.0 (9)S1A—C20A—H20A109.5
C11A—C10A—H10A120.5S1A—C20A—H20B109.5
C9A—C10A—H10A120.5H20A—C20A—H20B109.5
C10A—C11A—C12A120.3 (12)S1A—C20A—H20C109.5
C10A—C11A—H11A119.9H20A—C20A—H20C109.5
C12A—C11A—H11A119.9H20B—C20A—H20C109.5
C11A—C12A—C13A120.3 (13)S1A—C21A—H21A109.5
C11A—C12A—H12A119.9S1A—C21A—H21B109.5
C13A—C12A—H12A119.9H21A—C21A—H21B109.5
C12A—C13A—C8A120.9 (12)S1A—C21A—H21C109.5
C12A—C13A—H13A119.6H21A—C21A—H21C109.5
C8A—C13A—H13A119.6H21B—C21A—H21C109.5
C9B—C8B—C13B115.2 (11)O3B—S1B—C21B108.4 (8)
C9B—C8B—Sn119.4 (9)O3B—S1B—C20B112.3 (15)
C13B—C8B—Sn125.0 (10)C21B—S1B—C20B96.8 (13)
C8B—C9B—C10B123.3 (9)S1B—O3B—Sn123.0 (4)
C8B—C9B—H9BA118.3S1B—C20B—H20D109.5
C10B—C9B—H9BA118.3S1B—C20B—H20E109.5
C11B—C10B—C9B119.4 (10)H20D—C20B—H20E109.5
C11B—C10B—H10B120.3S1B—C20B—H20F109.5
C9B—C10B—H10B120.3H20D—C20B—H20F109.5
C10B—C11B—C12B120.2 (12)H20E—C20B—H20F109.5
C10B—C11B—H11B119.9S1B—C21B—H21D109.5
C12B—C11B—H11B119.9S1B—C21B—H21E109.5
C11B—C12B—C13B119.4 (13)H21D—C21B—H21E109.5
C11B—C12B—H12B120.3S1B—C21B—H21F109.5
C13B—C12B—H12B120.3H21D—C21B—H21F109.5
C12B—C13B—C8B122.5 (12)H21E—C21B—H21F109.5
C12B—C13B—H13B118.7
Sn—O1—C1—O28.7 (5)C11B—C12B—C13B—C8B0.3 (16)
Sn—O1—C1—C1i171.7 (3)C9B—C8B—C13B—C12B0.4 (12)
C7—C2—C3—C41.3 (6)Sn—C8B—C13B—C12B172.0 (9)
Sn—C2—C3—C4175.3 (3)C19A—C14A—C15A—C16A0.2 (4)
C2—C3—C4—C50.7 (7)Sn—C14A—C15A—C16A177.1 (6)
C3—C4—C5—C60.5 (8)C14A—C15A—C16A—C17A0.3 (5)
C4—C5—C6—C71.1 (9)C15A—C16A—C17A—C18A1.0 (11)
C3—C2—C7—C61.9 (6)C16A—C17A—C18A—C19A1.6 (13)
Sn—C2—C7—C6175.8 (3)C17A—C18A—C19A—C14A1.4 (11)
C5—C6—C7—C21.8 (8)C15A—C14A—C19A—C18A0.7 (9)
C13A—C8A—C9A—C10A0.3 (5)Sn—C14A—C19A—C18A176.8 (6)
Sn—C8A—C9A—C10A177.7 (6)C19B—C14B—C15B—C16B0.2 (5)
C8A—C9A—C10A—C11A0.0 (6)Sn—C14B—C15B—C16B178.0 (6)
C9A—C10A—C11A—C12A0.4 (12)C14B—C15B—C16B—C17B0.1 (5)
C10A—C11A—C12A—C13A1.0 (16)C15B—C16B—C17B—C18B0.3 (10)
C11A—C12A—C13A—C8A1.3 (16)C16B—C17B—C18B—C19B0.2 (12)
C9A—C8A—C13A—C12A0.9 (12)C17B—C18B—C19B—C14B0.1 (11)
Sn—C8A—C13A—C12A178.4 (9)C15B—C14B—C19B—C18B0.4 (9)
C13B—C8B—C9B—C10B0.2 (5)Sn—C14B—C19B—C18B177.8 (6)
Sn—C8B—C9B—C10B172.7 (7)C20A—S1A—O3A—Sn119.3 (17)
C8B—C9B—C10B—C11B0.3 (6)C21A—S1A—O3A—Sn127.4 (10)
C9B—C10B—C11B—C12B0.5 (12)C21B—S1B—O3B—Sn135.9 (7)
C10B—C11B—C12B—C13B0.2 (16)C20B—S1B—O3B—Sn118.3 (13)
Symmetry code: (i) x+3/2, y+1/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20A—H20A···O2ii0.962.513.43 (4)162
C21A—H21A···O2ii0.962.603.49 (2)154
C21B—H21D···O1iii0.962.363.278 (19)160
Symmetry codes: (ii) x, y+1, z1/2; (iii) x+3/2, y+1/2, z+3/2.
 

Acknowledgements

SB thanks Francisco Javier Ríos-Merino (BUAP) for performing the data collection of one of the studied crystals.

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