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Organotin(IV) selenate derivatives – Crystal structure of [{(Ph3Sn)2SeO4} ⋅ CH3OH]n

  • Waly Diallo EMAIL logo , Hélène Cattey and Laurent Plasseraud EMAIL logo
Published/Copyright: July 2, 2021
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Main Group Metal Chemistry
From the journal Main Group Metal Chemistry Volume 44 Issue 1

Abstract

Crystallization of [(Ph3Sn)2SeO4] ⋅ 1.5H2O in methanol leads to the formation of [{(Ph3Sn)2SeO4} ⋅ CH3OH]n (1) which constitutes a new specimen of organotin(IV) selenate derivatives. In the solid state, complex 1 is arranged in polymeric zig-zag chains, composed of alternating Ph3Sn and SeO4 groups. In addition, pendant Ph3Sn ⋅ CH3OH moieties are branched along chains according to a syndiotactic organization and via Sn-O-Se connections. From a supramolecular point of view, intermolecular hydrogen bonds established between the selenate groups (uncoordinated oxygen) and the hydroxyl functions (CH3OH) of the pendant groups link the chains together.

Keywords: organotin(IV); selenium; Sn-O-Se moiety; crystal structure; inorganic chain

An inventory of crystallographic structures of organotin complexes exhibiting Sn-O-Se moieties was recently reviewed, highlighting the existence of a great diversity of compounds involving selenite, selenate and organoseleninate derivatives (Plasseraud, 2018). Based on bridging SeO42− groups, the class of organotin(IV) selenate exhibits the predominance of polymeric structures, involving in particular inorganic chains, with tin atoms exhibiting trigonal bipyramidal geometries. Recently, we completed this category by characterizing a new trimethyltin(IV) selenate specimen, [(Me3Sn)3(SeO4) (OH)]n, isolated from the reaction of [(Me2NH2)2SeO4] and Me3SnCl in methanol (Diallo et al., 2018). Continuing our investigation in this field, we report herein the crystal structure of [{(Ph3Sn)2SeO4} ⋅ CH3OH]n (1) resulting from the crystallization of [(Ph3Sn)2SeO4] ⋅ 1.5H2O in methanol. An X-ray diffraction study from a suitable single crystal revealed, in the solid state, an organization based on polymeric zig-zag chains with pendant Ph3Sn ⋅ CH3OH groups (Scheme 1).

Scheme 1 Molecular representation of 1 (Ph = C6H5) showing its zig-zag chain arrangement.
Scheme 1

Molecular representation of 1 (Ph = C6H5) showing its zig-zag chain arrangement.

In the past, some of us reported the synthesis and the characterization of [(Ph3Sn)2SeO4] ⋅ 1.5H2O which was prepared from H2SeO4 and triphenyltin hydroxide in ethanol (Diop et al., 2007). The recrystallization of [(Ph3Sn)2SeO4] ⋅ 1.5H2O in methanol causes the displacement of H2O and leads to the growth of colorless prism-shaped crystals characterized as the new triphenyltin(IV) selenate, [{(Ph3Sn)2SeO4} ⋅ CH3OH]n (1). The crystal structure of 1 was resolved by the X-ray diffraction. Selected crystallographic data and refinement details are reported in Table 1. An Olex2 view with selected bond lengths and angles [Å, °] is shown in Figure 1. The asymmetric unit of 1 contains two distinct tin(IV) atoms, each bearing three coplanar phenyl groups [Sn1-C13 = 2.119(4), Sn1-C1 = 2.119(4), Sn1-C7 = 2.123(4), Sn2-C26 = 2.119(4), Sn2-C32 = 2.130(4), and Sn2-C20 = 2.122(4) Å]. The two Sn atoms are trans-coordinated by two oxygen atoms and adopt a trigonal bipyramidal geometry (TBP). Values of O-Sn-O angles are almost linear [O2-Sn1-O1 = 178.55(10) and O5-Sn2-O4i = 176.48(9)°]. The structural indexes τ values of the Addison parameter (Addison et al., 1984) determined for Sn1 and Sn2 (0.950 and 0.919, respectively) indicate a distorted character for each TBP, which is consistent with earlier reports (Parvez et al., 2000). The apical positions of Sn2 are occupied by two oxygen atoms of two distinct tetrahedral selenate groups acting as tridentate and triply bridging ligand [O5-Sn2 = 2.230(2) and O4i-Sn2 = 2.285(2) Å]. For Sn1, one apical position is occupied by one oxygen atom of SeO42− [Sn1-O2 = 2.213(3) Å], and the second by the oxygen atom of a coordinated CH3OH molecule [Sn1-O1 = 2.320(3) Å]. The Sn-O(Se) distances of 1 are in the range of those already reported for triphenyltin(IV) selenates [2.15–2.31 Å] (Plasseraud, 2018). Regarding the Ph3Sn-O(H)CH3 distance [Sn1-O1 = 2.320(3) Å], a comparable value was recorded for [(Ph3Sn)2CrO4] ⋅ CH3OH [2.361(3) Å] which is structurally similar to 1. [(Ph3Sn)2CrO4] ⋅ CH3OH was previously characterized as polymer chains resulting from the association of Ph3Sn moieties linked to tridentate CrO4 groups, and bearing also pendant Ph3Sn-O(H)CH3 units (Diallo et al., 2007).

Figure 1 Crystal structure of 1 showing 50% probability ellipsoids and the crystallographic numbering scheme (Olex2 view). Selected bond lengths and angles [Å, °]: Sn1-O1 2.320(3), Sn1-O2 2.213(3), Sn1-C1 2.119(4), Sn1-C7 2.123(4), Sn1-C13 2.119(4), Sn2-O5 2.230(2), Sn2-O4i 2.285(2), Sn2-C20 2.122(4), Sn2-C26 2.119(4), Sn2-C32 2.130(4), Se-O2 1.650(3), Se-O3 1.616(3), Se-O4 1.636(3), Se-O5 1.651(2), C19-O1 1.464(5); C13-Sn1-C7 117.07(16), C1-Sn1-C7 120.93(14), C1-Sn1-C13 121.54(14), C26-Sn2-C32 121.34(15), C26-Sn2-C20 119.84(15), C20-Sn2-C32 118.59(16), Se-O2-Sn1 139.91(14), Se-O5-Sn2 133.94(14), O4-Se-O5 107.04(13), O4-Se-O2 108.48(13), O2-Se-O5 107.71(13), O3-Se-O5 110.65(12), O3-Se-O4 113.23(13), O3-Se-O2 109.55(14), C19-O1-Sn1 115.4(2), [Symmetry operation: i = ½ + x, ½ − y, 1-z; ii = −½ + x, ½ − y, 1 − z].
Figure 1

Crystal structure of 1 showing 50% probability ellipsoids and the crystallographic numbering scheme (Olex2 view). Selected bond lengths and angles [Å, °]: Sn1-O1 2.320(3), Sn1-O2 2.213(3), Sn1-C1 2.119(4), Sn1-C7 2.123(4), Sn1-C13 2.119(4), Sn2-O5 2.230(2), Sn2-O4i 2.285(2), Sn2-C20 2.122(4), Sn2-C26 2.119(4), Sn2-C32 2.130(4), Se-O2 1.650(3), Se-O3 1.616(3), Se-O4 1.636(3), Se-O5 1.651(2), C19-O1 1.464(5); C13-Sn1-C7 117.07(16), C1-Sn1-C7 120.93(14), C1-Sn1-C13 121.54(14), C26-Sn2-C32 121.34(15), C26-Sn2-C20 119.84(15), C20-Sn2-C32 118.59(16), Se-O2-Sn1 139.91(14), Se-O5-Sn2 133.94(14), O4-Se-O5 107.04(13), O4-Se-O2 108.48(13), O2-Se-O5 107.71(13), O3-Se-O5 110.65(12), O3-Se-O4 113.23(13), O3-Se-O2 109.55(14), C19-O1-Sn1 115.4(2), [Symmetry operation: i = ½ + x, ½ − y, 1-z; ii = −½ + x, ½ − y, 1 − z].

Table 1

Crystal data and structure refinement of 1

Formula C37H34O5SeSn2
Formula weight, g·mol−1 874.98
Crystal system Orthorhombic
Space group P212121
a, Å 12.6189(3) Å
b, Å 15.4979(4) Å
c, Å 17.1412(4) Å
α, ° 90
β, ° 90
β, ° 90
V, Å3 3352.24(14)
Z 4
ρcalcd, g·cm−3 1.734
T, K 115
μ (Mo Kα), mm−1 2.618 mm−1
F(000) 1720
θ range, ° 2.40–27.49
Index ranges −12 ≤ h ≤ 16
−20 ≤ k ≤ 20,
−22 ≤ l ≤ 22
No. of reflections collected 22656
Completeness to θmax 99.00%
No. of independent reflections 7638
No. of observed reflections with [I > 2 σ (I)] 6939
No. of refined parameters 410
Goodness of fit on (F2) 0.967
R1 (F) [I > 2σ(I)] 0.0238
wR 2 (F2) (all data) 0.0367
(Δ/σ) max 0.001
Largest diffraction peak/hole, e/Å3 0.479/−0.403

In the crystal lattice, [{(Ph3Sn)2SeO4} ⋅ CH3OH]n (1) is organized in infinite zig-zag chains, propagating along the a-axis and whose structure is based on alternating Ph3Sn+ and SeO42− building-blocks (Figure 2). In addition, non-coordinated oxygen atoms of selenate anions are involved in intermolecular hydrogen bonding interactions with hydroxyl groups of methanol molecule of neighboring chains [O ⋅ ⋅ ⋅ H-O = 2.663 Å]. This results in the propagation of a grid-shaped three-dimensional network depicted in Figure 3.

Figure 2 The infinite chain of 1 propagating along the a-axis (Mercury view) [Sn (light blue), Se (yellow), O (red), C (grey)]. Hydrogen atoms and phenyl groups are omitted for clarity.
Figure 2

The infinite chain of 1 propagating along the a-axis (Mercury view) [Sn (light blue), Se (yellow), O (red), C (grey)]. Hydrogen atoms and phenyl groups are omitted for clarity.

Figure 3 Mercury view of the grid-shaped network resulting from the presence of intermolecular hydrogen bonds (blue dotted) between polymeric chains of 1. Phenyl groups are omitted for clarity.
Figure 3

Mercury view of the grid-shaped network resulting from the presence of intermolecular hydrogen bonds (blue dotted) between polymeric chains of 1. Phenyl groups are omitted for clarity.

Infrared spectroscopy analysis of 1 mainly shows the absorption bands corresponding to νSeO4 at 818, 727, and 693 cm−1 (Baran et al., 1997; Ben Hassen et al., 2014; Soukrata et al., 2014). In solution, despite the difficulties of solubilization in usual solvents, we were able to obtain the 119Sn NMR fingerprint of 1 in CD3OD showing two broad resonances at δ-193.6 and δ-215.1 ppm. The synthetic precursor, [(Ph3Sn)2SeO4] ⋅ 1.5H2O, exhibited only one resonance at δ-213.0 ppm (Diop et al., 2007). These values of chemical shift, are consistent with five-coordinated tin(IV) atoms in a trans trigonal bipyramidal geometry environment (Holeček et al., 1983) and support for 1 the preservation of the structure in solution. For comparison, the chromato structural analogue of 1, [(Ph3Sn)2CrO4] ⋅ CH3OH, exhibits in CDCl3 only one resonance at δ-44 pm, which was explained by the disruption of the polymeric chains and reflecting the four-coordination environment of tin atoms in solution (Diallo et al., 2007). Regarding the 13C{1H} NMR spectrum of 1, carbon atoms of the phenyl groups exhibit chemical shifts comparable to [(Ph3Sn)2SeO4] ⋅ 1.5H2O (Diop et al., 2007), however the resonance corresponding to the ipso carbon is not visible.

In summary, the complex of [{(Ph3Sn)2SeO4} ⋅ CH3OH]n (1) constitutes a new specimen of triorganotin(IV) selenate and thus extends this class of compounds predisposed to lead to the development of inorganic polymer networks.

Experimental

General

[(Ph3Sn)2SeO4] ⋅ 1.5H2O was prepared according to a previously published procedure (Diop et al., 2007). Infrared spectra were recorded on a Bruker Vector 22 spectrometer (Wissenbourg, France) equipped with a Specac Golden GateTM ATR device. 1H, 13C{1H} and 119Sn{1H} spectra were recorded on a Bruker Avance 300 spectrometer in CD3OD. 1H and 13C{1H} chemical shifts (δ, ppm) were determined from the residual solvent signal (CH3OH δ = 3.31 and CH3OH δ = 49.00). 119Sn{1H} chemical shifts (δ, ppm) were reported downfield from (CH3)4Sn used as external standard. Elemental analyses were performed at the “Plateforme d’Analyse Chimique et de Synthèse Moléculaire de l’Université de Bourgogne (PACSMUB)” on a Fisons EA 1108 CHNS-O apparatus.

Isolation of [{(Ph3Sn)2SeO4} ⋅ CH3OH]n (1)

An amount of [(Ph3Sn)2SeO4] ⋅ 1.5H2O (0.3 g) was dissolved at room temperature in methanol (20 mL). Suitable colorless prism-shape crystals were obtained after few days of evaporation (37 % yield) and characterized by single-crystal X-ray diffraction as [{(Ph3Sn)2SeO4} ⋅ CH3OH]n (1). Compound 1 is relatively stable over time and in ambient air (no significant degradation observed), which facilitated its handling and characterization.

1H-NMR (ppm): δ = 7.75 [br, 12H, phenyl protons, J(117,119Sn-H) = 63 Hz]; δ = 7.42 [br, 18H, phenyl protons], δ = 3.34 [s, 3H, CH3OH]. 13C{1H}-NMR (ppm): δ = 137.6, C(o) [J(117,119Sn-C) = 46 Hz]; δ = 130.9, C(p), δ = 129.9, C(m) [J(117,119Sn-C) = 70 Hz]. 119Sn{1H}-NMR (ppm): −193.6; −215.1. IR (ATR, cm−1): 3046 (w), 1622 (w), 1578 (w), 1480 (w), 1430 (m), 1075 (w), 1023 (w), 998 (w), 818 (s), 727 (s), 693 (s). Anal. Calc. for C37H34O5SeSn2 (804.04 g·mol−1): Calc: C 50.79, H 3.92. Found: C 50.49, H 4.00.

X-ray crystallography

A suitable crystal of 1 was selected and mounted on a mylar loop with oil. Crystallographic data collection was recorded with a Bruker Kappa Apex II diffractometer. The crystal (0.33 × 0.25 × 0.12 mm) was kept at T = 115 K during data collection. Using OLEX2 (Dolomanov et al., 2009), the structure was solved with the XT (Sheldrick, 2015) structure solution program, using the Intrinsic Phasing solution method. The model was refined with version 2014/7 of XL (Sheldrick, 2008) using Least Squares minimisation. All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model. Programs used for the representation of the molecular and crystal structures: Olex2 (Dolomanov et al., 2009), and Mercury (Macrae et al., 2008).

Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Centre, CCDC numbers 2080826. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44-1223-336033; e-mail: or http://www.ccdc.cam.ac.uk).

  1. Funding information:

    This work was supported by the Cheikh Anta Diop University of Dakar (Senegal), the Centre National de la Recherche Scientifique (CNRS, France) and the University of Bourgogne Franche-Comté (Dijon, France).

  2. Author contributions:

    Waly Diallo: conceptualization, investigation, writing – original draft; Hélène Cattey: investigation – crystal analysis, review; Laurent Plasseraud: supervision, writing – review and editing.

  3. Conflict of interest:

    Authors state no conflict of interest.

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Received: 2021-05-03
Accepted: 2021-05-28
Published Online: 2021-07-02

© 2021 Waly Diallo et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/mgmc-2021-0023
Keywords for this article
organotin(IV); selenium; Sn-O-Se moiety; crystal structure; inorganic chain
Creative Commons
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Articles in the same Issue

  1. Research Articles
  2. A novel approach for the production of zinc borate (4ZnO·B2O3·H2O) using a single-step hydrothermal method
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