metal-organic compounds
catena-Poly[[trimethyltin(IV)]-μ-3,4-difluorobenzeneseleninato-κ2O:O′]
aDepartment of Pharmacy, Shandong Medical College, Jinan 250000, People's Republic of China, and bSchool of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
*Correspondence e-mail: zhangrf856@163.com
The title compound, [Sn(CH3)3(C6H3F2O2Se)]n, was prepared by treatment of 3,4-difluorobenzeneseleninic acid and trimethyltin chloride with sodium ethoxide in methanol. In the polymeric infinite chains, with the SnIV atom in a trigonal–bipyramidal C3O2 coordination environment involving methyl ligands and the bridging 3,4-difluorobenzeneseleninate anion, are present. The chains extend parallel to [010] and are linked through slipped π–π interactions and weak C—H⋯O hydrogen bonds into a three-dimensional network.
Keywords: crystal structure; organotin complex; 3,4-difluorobenzeneseleninic acid; trimethyltin(IV); polymeric chain.
CCDC reference: 1578937
Structure description
In recent years, organotin complexes have been attracting attention due to their significant number of industrial applications and their biological activities (Dubey & Roy, 2003; Gielen, 2002). As part of our ongoing investigations in this field (Ma et al., 2011), we have synthesized the title compound and present its here.
As can been seen from Fig. 1, the of the title compound consists of one [(CH3)3Sn] moiety and a deprotonated 3,4-difluorobenzeneseleninate anion that bridges adjacent SnIV atoms. The geometric index τ5 (Addison et al., 1984) of Sn1 is 0.83, indicating a distorted trigonal–bipyramidal coordination environment whereby two O atoms from two 3,4-difluorobenzeneseleninate anions occupy the axial positions [O2—Sn1—O1A(−x + , y − , −z + ) = 171.53 (11)°] and the methyl C atoms occupy the equatorial sites (C—Sn1—C angle sum is 359.9°). The OSeO units of the 3,4-difluorobenzeneseleninate anion link adjacent [Me3Sn]+ moieties into a zigzag chain structure extending parallel to [010] (Fig. 2). As a result of weak C—H⋯O hydrogen-bonding interactions (Table 1) and slipped π–π interactions between the difluorobenzene rings of adjacent chains (plane-to-plane distance = 3.538 Å), a three-dimensional network is established (Fig. 3).
Synthesis and crystallization
All reactions were carried out under a nitrogen atmosphere using standard Schlenk techniques. The title compound was synthesized by dissolving 3,4-difluorobenzeneseleninic acid (0.225 g, 1.0 mmol) and sodium ethoxide (0.068 g, 1.0 mmol) in methanol (30 ml) under stirring for 30 min. Trimethyltin chloride (0.199 g, 1.0 mmol) was then added and the mixture stirred for a further 12 h at 323 K. The reaction mixture was filtered and the solvent gradually evaporated under vacuum until a colourless solid was obtained. The resulting product was recrystallized from diethyl ether to give transparent colourless crystals of the title compound (yield 80%, m.p. 413–415 K). Analysis calculated for C9H12O2F2SeSn: C 27.87, H 3.12%; found: C 27.67, H 3.38%.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1578937
https://doi.org/10.1107/S2414314617014572/wm4058sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014572/wm4058Isup2.hkl
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).[Sn(CH3)3(C6H3F2O2Se)] | F(000) = 1472 |
Mr = 387.84 | Dx = 1.939 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.0109 (15) Å | Cell parameters from 3059 reflections |
b = 10.5246 (8) Å | θ = 2.6–27.9° |
c = 14.0791 (11) Å | µ = 4.67 mm−1 |
β = 95.443 (2)° | T = 298 K |
V = 2656.8 (4) Å3 | Block, colorless |
Z = 8 | 0.45 × 0.25 × 0.18 mm |
Bruker APEXIII CCD area detector diffractometer | 2336 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
phi and ω scans | θmax = 28.2°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −23→23 |
Tmin = 0.228, Tmax = 0.487 | k = −13→10 |
7837 measured reflections | l = −18→17 |
3199 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0403P)2 + 2.010P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.017 |
3199 reflections | Δρmax = 0.98 e Å−3 |
139 parameters | Δρmin = −0.82 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.27668 (2) | 0.51508 (3) | 0.69692 (2) | 0.03983 (12) | |
Se1 | 0.19978 (3) | 0.81568 (4) | 0.60742 (3) | 0.03991 (14) | |
F1 | −0.1054 (2) | 0.6237 (5) | 0.4668 (4) | 0.1246 (16) | |
F2 | 0.0018 (3) | 0.6159 (7) | 0.3566 (4) | 0.171 (3) | |
O1 | 0.1875 (2) | 0.8348 (3) | 0.7241 (2) | 0.0519 (8) | |
O2 | 0.25046 (18) | 0.6830 (3) | 0.6011 (2) | 0.0447 (8) | |
C1 | 0.0180 (4) | 0.6642 (7) | 0.4431 (5) | 0.082 (2) | |
C2 | 0.0887 (3) | 0.7068 (6) | 0.4718 (4) | 0.0660 (15) | |
H2 | 0.1265 | 0.7041 | 0.4313 | 0.079* | |
C3 | 0.1010 (3) | 0.7533 (5) | 0.5628 (3) | 0.0479 (11) | |
C4 | 0.0444 (3) | 0.7563 (7) | 0.6227 (4) | 0.0735 (17) | |
H4 | 0.0544 | 0.7872 | 0.6845 | 0.088* | |
C5 | −0.0279 (4) | 0.7138 (8) | 0.5922 (6) | 0.105 (3) | |
H5 | −0.0665 | 0.7163 | 0.6315 | 0.126* | |
C6 | −0.0376 (3) | 0.6687 (7) | 0.5012 (6) | 0.085 (2) | |
C7 | 0.1736 (3) | 0.5143 (5) | 0.7559 (4) | 0.0643 (16) | |
H7A | 0.1438 | 0.5842 | 0.7304 | 0.096* | |
H7B | 0.1820 | 0.5224 | 0.8240 | 0.096* | |
H7C | 0.1481 | 0.4359 | 0.7401 | 0.096* | |
C8 | 0.3657 (4) | 0.6155 (6) | 0.7734 (5) | 0.088 (2) | |
H8A | 0.3673 | 0.5947 | 0.8399 | 0.132* | |
H8B | 0.3579 | 0.7052 | 0.7652 | 0.132* | |
H8C | 0.4120 | 0.5920 | 0.7496 | 0.132* | |
C9 | 0.2920 (3) | 0.4116 (5) | 0.5720 (4) | 0.0658 (15) | |
H9A | 0.2847 | 0.3228 | 0.5834 | 0.099* | |
H9B | 0.3416 | 0.4253 | 0.5547 | 0.099* | |
H9C | 0.2565 | 0.4397 | 0.5211 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0463 (2) | 0.03474 (18) | 0.03778 (19) | 0.00020 (13) | 0.00044 (13) | 0.00274 (13) |
Se1 | 0.0516 (3) | 0.0288 (2) | 0.0381 (3) | −0.00090 (18) | −0.0022 (2) | 0.00034 (18) |
F1 | 0.053 (2) | 0.167 (4) | 0.147 (4) | −0.030 (3) | −0.023 (2) | 0.000 (4) |
F2 | 0.113 (4) | 0.271 (8) | 0.125 (4) | −0.044 (4) | −0.014 (3) | −0.087 (5) |
O1 | 0.074 (2) | 0.0423 (18) | 0.0393 (18) | −0.0108 (16) | 0.0059 (16) | −0.0103 (15) |
O2 | 0.0548 (19) | 0.0376 (17) | 0.0414 (18) | 0.0073 (14) | 0.0029 (15) | 0.0071 (14) |
C1 | 0.075 (4) | 0.092 (5) | 0.072 (4) | −0.010 (4) | −0.027 (4) | −0.021 (4) |
C2 | 0.057 (3) | 0.082 (4) | 0.057 (3) | −0.006 (3) | −0.001 (3) | −0.014 (3) |
C3 | 0.049 (3) | 0.042 (3) | 0.050 (3) | 0.005 (2) | −0.009 (2) | 0.000 (2) |
C4 | 0.057 (3) | 0.105 (5) | 0.058 (4) | 0.000 (4) | 0.004 (3) | −0.005 (4) |
C5 | 0.077 (5) | 0.138 (7) | 0.093 (6) | −0.006 (5) | −0.023 (4) | −0.002 (6) |
C6 | 0.042 (4) | 0.097 (5) | 0.115 (6) | −0.013 (3) | −0.009 (4) | 0.014 (5) |
C7 | 0.064 (4) | 0.060 (3) | 0.072 (4) | 0.009 (3) | 0.022 (3) | 0.015 (3) |
C8 | 0.094 (5) | 0.060 (4) | 0.099 (5) | −0.020 (3) | −0.046 (4) | 0.015 (4) |
C9 | 0.099 (5) | 0.049 (3) | 0.050 (3) | 0.014 (3) | 0.013 (3) | −0.002 (3) |
Sn1—C7 | 2.104 (5) | C3—C4 | 1.383 (7) |
Sn1—C9 | 2.108 (5) | C4—C5 | 1.404 (9) |
Sn1—C8 | 2.125 (6) | C4—H4 | 0.9300 |
Sn1—O2 | 2.247 (3) | C5—C6 | 1.363 (10) |
Sn1—O1i | 2.262 (3) | C5—H5 | 0.9300 |
Se1—O2 | 1.675 (3) | C7—H7A | 0.9600 |
Se1—O1 | 1.690 (3) | C7—H7B | 0.9600 |
Se1—C3 | 1.944 (5) | C7—H7C | 0.9600 |
F1—C6 | 1.355 (7) | C8—H8A | 0.9600 |
F2—C1 | 1.326 (7) | C8—H8B | 0.9600 |
O1—Sn1ii | 2.262 (3) | C8—H8C | 0.9600 |
C1—C6 | 1.352 (10) | C9—H9A | 0.9600 |
C1—C2 | 1.374 (8) | C9—H9B | 0.9600 |
C2—C3 | 1.370 (7) | C9—H9C | 0.9600 |
C2—H2 | 0.9300 | ||
C7—Sn1—C9 | 121.1 (2) | C5—C4—H4 | 119.3 |
C7—Sn1—C8 | 116.9 (3) | C6—C5—C4 | 115.6 (7) |
C9—Sn1—C8 | 121.8 (3) | C6—C5—H5 | 122.2 |
C7—Sn1—O2 | 95.57 (16) | C4—C5—H5 | 122.2 |
C9—Sn1—O2 | 86.66 (16) | C1—C6—F1 | 117.8 (7) |
C8—Sn1—O2 | 91.06 (19) | C1—C6—C5 | 123.0 (6) |
C7—Sn1—O1i | 91.36 (17) | F1—C6—C5 | 119.3 (7) |
C9—Sn1—O1i | 85.58 (16) | Sn1—C7—H7A | 109.5 |
C8—Sn1—O1i | 90.13 (19) | Sn1—C7—H7B | 109.5 |
O2—Sn1—O1i | 171.53 (11) | H7A—C7—H7B | 109.5 |
O2—Se1—O1 | 105.85 (16) | Sn1—C7—H7C | 109.5 |
O2—Se1—C3 | 100.84 (18) | H7A—C7—H7C | 109.5 |
O1—Se1—C3 | 98.87 (19) | H7B—C7—H7C | 109.5 |
Se1—O1—Sn1ii | 121.34 (16) | Sn1—C8—H8A | 109.5 |
Se1—O2—Sn1 | 135.08 (17) | Sn1—C8—H8B | 109.5 |
F2—C1—C6 | 117.2 (6) | H8A—C8—H8B | 109.5 |
F2—C1—C2 | 120.8 (7) | Sn1—C8—H8C | 109.5 |
C6—C1—C2 | 122.0 (6) | H8A—C8—H8C | 109.5 |
C3—C2—C1 | 117.1 (6) | H8B—C8—H8C | 109.5 |
C3—C2—H2 | 121.5 | Sn1—C9—H9A | 109.5 |
C1—C2—H2 | 121.5 | Sn1—C9—H9B | 109.5 |
C2—C3—C4 | 121.0 (5) | H9A—C9—H9B | 109.5 |
C2—C3—Se1 | 119.0 (4) | Sn1—C9—H9C | 109.5 |
C4—C3—Se1 | 120.0 (4) | H9A—C9—H9C | 109.5 |
C3—C4—C5 | 121.4 (6) | H9B—C9—H9C | 109.5 |
C3—C4—H4 | 119.3 | ||
O2—Se1—O1—Sn1ii | 123.4 (2) | Se1—C3—C4—C5 | 179.0 (6) |
C3—Se1—O1—Sn1ii | −132.6 (2) | C3—C4—C5—C6 | 0.8 (11) |
O1—Se1—O2—Sn1 | 18.4 (3) | F2—C1—C6—F1 | 0.0 (11) |
C3—Se1—O2—Sn1 | −84.1 (3) | C2—C1—C6—F1 | −179.6 (7) |
F2—C1—C2—C3 | −179.0 (7) | F2—C1—C6—C5 | 178.7 (8) |
C6—C1—C2—C3 | 0.6 (10) | C2—C1—C6—C5 | −0.9 (12) |
C1—C2—C3—C4 | 0.3 (9) | C4—C5—C6—C1 | 0.2 (12) |
C1—C2—C3—Se1 | −179.7 (5) | C4—C5—C6—F1 | 178.8 (7) |
C2—C3—C4—C5 | −1.0 (10) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2iii | 0.93 | 2.59 | 3.370 (7) | 142 |
Symmetry code: (iii) −x+1/2, −y+3/2, −z+1. |
Funding information
Funding for this research was provided by: National Nature Science Foundation of China (grant No. 21371087).
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