catena-Poly[[tri­methyl­tin(IV)]-μ-methyl­phenyl­phosphinato-κ2O:O′]

Fu, C.; Zhang, R.; Zhang, S.

doi:10.1107/S2414314617014420

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171442

https://doi.org/10.1107/S2414314617014420

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catena-Poly[[trimethyltin(IV)]-μ-methylphenylphosphinato-κ²O:O′]

Chunhua Fu,^a Rufen Zhang ^b ^* and Shaoliang Zhang ^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 J. Simpson, University of Otago, New Zealand (Received 24 September 2017; accepted 6 October 2017; online 13 October 2017)

A new trimethyltin(IV) coordination polymer, [Sn(CH₃)₃(C₇H₈O₂P)], has been prepared by treatment of methylphenylphosphinic acid and trimethyltin chloride with sodium ethoxide in methanol. In the solid state, the title compound adopts an infinite one-dimensional polymeric chain structure with each Sn^IV atom adopting a distorted trigonal–bipyramidal geometry.

Keywords: crystal structure; organotin; methylphenylphosphinic acid; trimethyltin(IV); coordination compound; polymeric chain.

CCDC reference: 1578530

Structure description

In recent years, organotin complexes have been attracting more and more attention due to their significant number of industrial applications and their biological activity (Dubey & Roy, 2003 ; Gielen, 2002 ). As a part of our ongoing investigations in this field (Ma et al., 2008 ), 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] group and a deprotonated methylphenylphosphinic acid. Each Sn^IV atom adopts a distorted trigonal–bipyramidal geometry where the two oxygen atoms from the bridging methylphenylphosphinate ligands occupy the axial positions [O1—Sn1—O2( $[{3\over 2}]$ − x, $[{3\over 2}]$ + y, $[{1\over 2}]$ − z) = 178.6 (3)°]. The three C atoms of the [Me₃Sn]⁺ group are equatorial with the three trigonal C—Sn1—C angles summing to 359.9°. Hence atoms Sn1, C8, C9 and C10 are almost coplanar with an r.m.s. deviation of 0.0128 Å from the best fit plane through these atoms. Two P(=O)O– units of the deprotonated methylphenylphosphinic acid ligand link adjacent [Me₃Sn]⁺ atoms into a one-dimensional zigzag chain structure along the b-axis direction (Fig. 2).

Figure 1
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids.

Figure 2
View of the one-dimensional zigzag chain structure running parallel to the b axis in the title compound. H atoms have been omitted for clarity.

Synthesis and crystallization

The reaction was carried out under a nitrogen atmosphere using standard Schlenk techniques. The compound was synthesized by dissolving methylphenylphosphinic acid (0.156 g, 1.0 mmol), sodium ethoxide (0.068 g, 1.0 mmol) in methanol (30 ml) and stirring for 30 min. Trimethyltin chloride (0.199 g, 1.0 mmol) was then added and stirred for further 12 h at 318 K. The reaction mixture was filtered and the solvent was gradually evaporated under vacuum until a white solid product was obtained. The resulting product was recrystallized from diethyl ether to give transparent colourless crystals of the title compound (yield 88%, m.p. 428–430 K). Analysis calculated for C₁₀H₁₇O₂PSn: C 37.66, H 5.37%; found: C 37.43, H 5.48%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₇H₈O₂P)]
M_r	318.89
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.8051 (11), 10.3376 (13), 12.4466 (15)
β (°)	103.485 (1)
V (Å³)	1351.9 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.99
Crystal size (mm)	0.48 × 0.45 × 0.33

Data collection
Diffractometer	Bruker APEXIII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.449, 0.560
No. of measured, independent and observed [I > 2σ(I)] reflections	5890, 2371, 1581
R_int	0.120
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.266, 1.05
No. of reflections	2371
No. of parameters	131
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.75, −2.29
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1578530

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617014420/sj4133sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014420/sj4133Isup2.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-methylphenylphosphinato-κ²O:O'] top

Crystal data top

[Sn(CH₃)₃(C₇H₈O₂P)]	F(000) = 632
M_r = 318.89	D_x = 1.567 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.8051 (11) Å	Cell parameters from 2834 reflections
b = 10.3376 (13) Å	θ = 2.3–27.2°
c = 12.4466 (15) Å	µ = 1.99 mm⁻¹
β = 103.485 (1)°	T = 298 K
V = 1351.9 (3) Å³	Block, colorless
Z = 4	0.48 × 0.45 × 0.33 mm

Data collection top

Bruker APEXIII CCD area detector diffractometer	1581 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.120
phi and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −12→12
T_min = 0.449, T_max = 0.560	k = −12→9
5890 measured reflections	l = −13→14
2371 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.085	H-atom parameters constrained
wR(F²) = 0.266	w = 1/[σ²(F_o²) + (0.1668P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2371 reflections	Δρ_max = 2.75 e Å⁻³
131 parameters	Δρ_min = −2.29 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	0.79793 (7)	0.62599 (8)	0.22275 (6)	0.0396 (4)
P1	0.8534 (4)	0.3397 (3)	0.1053 (3)	0.0471 (9)
O1	0.8773 (10)	0.4803 (8)	0.1248 (8)	0.067 (3)
O2	0.7787 (10)	0.2766 (9)	0.1787 (8)	0.066 (3)
C1	1.0072 (12)	0.2600 (11)	0.1224 (10)	0.044 (3)
C2	1.1181 (14)	0.3355 (15)	0.1300 (13)	0.064 (4)
H2	1.1134	0.4253	0.1277	0.077*
C3	1.2345 (15)	0.273 (2)	0.1408 (14)	0.085 (5)
H3	1.3083	0.3213	0.1458	0.102*
C4	1.2404 (18)	0.1382 (18)	0.1441 (15)	0.081 (5)
H4	1.3180	0.0964	0.1503	0.097*
C5	1.1335 (18)	0.0686 (18)	0.1384 (13)	0.078 (5)
H5	1.1388	−0.0211	0.1432	0.094*
C6	1.0176 (16)	0.1269 (13)	0.1256 (13)	0.061 (4)
H6	0.9450	0.0765	0.1190	0.073*
C7	0.7727 (16)	0.3131 (19)	−0.0378 (12)	0.080 (5)
H7A	0.7518	0.2231	−0.0490	0.119*
H7B	0.8275	0.3384	−0.0847	0.119*
H7C	0.6961	0.3637	−0.0554	0.119*
C8	0.9178 (13)	0.7666 (12)	0.1790 (12)	0.055 (3)
H8A	0.9294	0.8363	0.2314	0.082*
H8B	0.8799	0.7994	0.1066	0.082*
H8C	0.9988	0.7285	0.1789	0.082*
C9	0.6111 (15)	0.6020 (15)	0.1233 (12)	0.067 (4)
H9A	0.5694	0.5328	0.1523	0.100*
H9B	0.6155	0.5818	0.0490	0.100*
H9C	0.5639	0.6806	0.1236	0.100*
C10	0.8716 (15)	0.5208 (15)	0.3710 (11)	0.070 (4)
H10A	0.8054	0.5079	0.4096	0.104*
H10B	0.9401	0.5687	0.4169	0.104*
H10C	0.9026	0.4384	0.3532	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0286 (6)	0.0407 (6)	0.0522 (6)	0.0003 (3)	0.0145 (4)	0.0010 (3)
P1	0.051 (2)	0.0397 (18)	0.060 (2)	0.0044 (15)	0.0310 (17)	0.0035 (15)
O1	0.080 (7)	0.042 (5)	0.096 (7)	0.015 (5)	0.058 (6)	0.009 (5)
O2	0.078 (7)	0.043 (5)	0.094 (7)	0.001 (5)	0.057 (6)	0.012 (5)
C1	0.043 (7)	0.040 (7)	0.056 (7)	0.000 (6)	0.029 (6)	0.008 (6)
C2	0.049 (9)	0.059 (9)	0.088 (11)	0.001 (7)	0.024 (8)	−0.010 (8)
C3	0.038 (9)	0.113 (15)	0.103 (13)	−0.003 (9)	0.016 (9)	0.001 (11)
C4	0.054 (11)	0.109 (16)	0.080 (11)	0.028 (10)	0.020 (9)	0.007 (9)
C5	0.088 (14)	0.062 (10)	0.095 (12)	0.025 (10)	0.040 (10)	−0.003 (9)
C6	0.058 (10)	0.057 (9)	0.076 (10)	0.015 (7)	0.030 (8)	0.002 (7)
C7	0.066 (11)	0.113 (13)	0.060 (9)	−0.001 (10)	0.017 (8)	−0.021 (9)
C8	0.037 (8)	0.044 (7)	0.095 (10)	0.002 (6)	0.040 (7)	−0.006 (7)
C9	0.050 (9)	0.090 (12)	0.064 (9)	0.004 (8)	0.019 (7)	0.006 (8)
C10	0.068 (11)	0.073 (10)	0.064 (9)	0.010 (8)	0.008 (8)	0.008 (7)

Geometric parameters (Å, º) top

Sn1—C8	2.101 (13)	C4—H4	0.9300
Sn1—C9	2.122 (15)	C5—C6	1.36 (2)
Sn1—C10	2.129 (13)	C5—H5	0.9300
Sn1—O1	2.231 (9)	C6—H6	0.9300
Sn1—O2ⁱ	2.255 (8)	C7—H7A	0.9600
P1—O1	1.486 (9)	C7—H7B	0.9600
P1—O2	1.502 (9)	C7—H7C	0.9600
P1—C7	1.812 (15)	C8—H8A	0.9600
P1—C1	1.822 (13)	C8—H8B	0.9600
O2—Sn1ⁱⁱ	2.255 (8)	C8—H8C	0.9600
C1—C6	1.380 (16)	C9—H9A	0.9600
C1—C2	1.415 (18)	C9—H9B	0.9600
C2—C3	1.39 (2)	C9—H9C	0.9600
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.40 (2)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.35 (2)

C8—Sn1—C9	119.3 (6)	C4—C5—C6	121.4 (17)
C8—Sn1—C10	116.7 (6)	C4—C5—H5	119.3
C9—Sn1—C10	123.9 (6)	C6—C5—H5	119.3
C8—Sn1—O1	89.3 (4)	C5—C6—C1	120.7 (16)
C9—Sn1—O1	92.1 (5)	C5—C6—H6	119.7
C10—Sn1—O1	90.9 (5)	C1—C6—H6	119.7
C8—Sn1—O2ⁱ	89.4 (4)	P1—C7—H7A	109.5
C9—Sn1—O2ⁱ	88.7 (5)	P1—C7—H7B	109.5
C10—Sn1—O2ⁱ	89.5 (5)	H7A—C7—H7B	109.5
O1—Sn1—O2ⁱ	178.6 (3)	P1—C7—H7C	109.5
O1—P1—O2	115.0 (5)	H7A—C7—H7C	109.5
O1—P1—C7	109.5 (8)	H7B—C7—H7C	109.5
O2—P1—C7	109.2 (7)	Sn1—C8—H8A	109.5
O1—P1—C1	107.7 (6)	Sn1—C8—H8B	109.5
O2—P1—C1	109.7 (5)	H8A—C8—H8B	109.5
C7—P1—C1	105.3 (7)	Sn1—C8—H8C	109.5
P1—O1—Sn1	132.5 (6)	H8A—C8—H8C	109.5
P1—O2—Sn1ⁱⁱ	161.4 (6)	H8B—C8—H8C	109.5
C6—C1—C2	119.1 (13)	Sn1—C9—H9A	109.5
C6—C1—P1	121.3 (11)	Sn1—C9—H9B	109.5
C2—C1—P1	119.6 (10)	H9A—C9—H9B	109.5
C3—C2—C1	118.9 (15)	Sn1—C9—H9C	109.5
C3—C2—H2	120.6	H9A—C9—H9C	109.5
C1—C2—H2	120.6	H9B—C9—H9C	109.5
C2—C3—C4	120.0 (16)	Sn1—C10—H10A	109.5
C2—C3—H3	120.0	Sn1—C10—H10B	109.5
C4—C3—H3	120.0	H10A—C10—H10B	109.5
C5—C4—C3	119.9 (17)	Sn1—C10—H10C	109.5
C5—C4—H4	120.1	H10A—C10—H10C	109.5
C3—C4—H4	120.1	H10B—C10—H10C	109.5

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2.

Funding information

We thank the National Natural Science Foundation of China (21371087) for financial support.

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