catena-Poly[[tri­methyl­tin(IV)]-μ-3,4-di­fluoro­benzene­seleninato-κ2O:O′]

Fu, C.; Zhang, R.; Yan, M.

doi:10.1107/S2414314617014572

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171457

https://doi.org/10.1107/S2414314617014572

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catena-Poly[[trimethyltin(IV)]-μ-3,4-difluorobenzeneseleninato-κ²O:O′]

Chunhua Fu,^a Rufen Zhang ^b ^* and Mao Yan ^b

^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

Edited by M. Weil, Vienna University of Technology, Austria (Received 29 September 2017; accepted 9 October 2017; online 20 October 2017)

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 crystal structure, infinite chains, with the Sn^IV 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 crystal structure here.

As can been seen from Fig. 1, the asymmetric unit of the title compound consists of one [(CH₃)₃Sn] moiety and a deprotonated 3,4-difluorobenzeneseleninate anion that bridges adjacent Sn^IV 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 + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ ) = 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).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.59	3.370 (7)	142
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Figure 1
The coordination environment of the Sn^IV atom, showing displacement ellipsoids at the 30% probability level. [Symmetry code: (A) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ .]

Figure 2
View of the polymeric chain structure in the title compound running parallel to [010]. H atoms have been omitted for clarity.

Figure 3
A perspective view along [100], showing the crystal packing of the title compound.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₆H₃F₂O₂Se)]
M_r	387.84
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	18.0109 (15), 10.5246 (8), 14.0791 (11)
β (°)	95.443 (2)
V (Å³)	2656.8 (4)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	4.67
Crystal size (mm)	0.45 × 0.25 × 0.18

Data collection
Diffractometer	Bruker APEXIII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.228, 0.487
No. of measured, independent and observed [I > 2σ(I)] reflections	7837, 3199, 2336
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.093, 1.04
No. of reflections	3199
No. of parameters	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.82
Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1578937

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617014572/wm4058sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014572/wm4058Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: 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).

catena-Poly[[trimethyltin(IV)]-µ-3,4-difluorobenzeneseleninato-κ²O:O'] top

Crystal data top

[Sn(CH₃)₃(C₆H₃F₂O₂Se)]	F(000) = 1472
M_r = 387.84	D_x = 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

Data collection top

Bruker APEXIII CCD area detector diffractometer	2336 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
phi and ω scans	θ_max = 28.2°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −23→23
T_min = 0.228, T_max = 0.487	k = −13→10
7837 measured reflections	l = −18→17
3199 independent reflections

Refinement top

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(F_o²) + (0.0403P)² + 2.010P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.017
3199 reflections	Δρ_max = 0.98 e Å⁻³
139 parameters	Δρ_min = −0.82 e Å⁻³

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	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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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