catena-Poly[[trimethyl­tin(IV)]-μ-(1,1′-binaphthyl-2,2′-diyl phospho­nato)]

Wu, J.; Zhang, R.

doi:10.1107/S160053680905291X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m63

doi:10.1107/S160053680905291X

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catena-Poly[[trimethyltin(IV)]-μ-(1,1′-binaphthyl-2,2′-diyl phosphonato)]

Jianjun Wu ^a and Rufen Zhang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China.
^*Correspondence e-mail: macl@lcu.edu.cn.

(Received 30 November 2009; accepted 9 December 2009; online 12 December 2009)

In the title polymeric coordination compound, [Sn(CH₃)₃(C₂₀H₁₂O₄P)]_n, the Sn atom exhibits a distorted trigonal-bipyramidal coordination geometry with the phosphate O atoms of the 1,1′-binaphthyl-2,2′-diyl phosphonate ligands in axial positions and equatorial sites occupied by the three methyl groups. Adjacent Sn atoms are bridged by coordination to the two O atoms of each 1,1′-binaphthyl-2,2′-diyl phosphonate ligand, forming a one-dimensional chain structure parallel to the b axis.

Related literature

For the biological activity of organotin compounds, see: Dubey & Roy (2003 ). For related structures, see: Wang et al. (2007 ); Ma et al. (2006 ).

Experimental

Crystal data

[Sn(CH₃)₃(C₂₀H₁₂O₄P)]
M_r = 511.06
Monoclinic, P 2₁ /c
a = 18.312 (2) Å
b = 10.665 (2) Å
c = 11.3361 (18) Å
β = 92.856 (2)°
V = 2211.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 298 K
0.42 × 0.21 × 0.13 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.621, T_max = 0.854
11194 measured reflections
3892 independent reflections
2695 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.085
S = 1.00
3892 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C21	2.101 (5)
Sn1—C22	2.113 (5)
Sn1—C23	2.123 (5)
Sn1—O3	2.253 (3)
Sn1—O4ⁱ	2.262 (3)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905291X/sj2705sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905291X/sj2705Isup2.hkl

checkCIF report

Comment top

In recent years, organotin complexes have been attracting more and more attention due to their wide industrial applications and biological activities (Dubey & Roy, 2003). As a part of our ongoing investigations in this field we have synthesized the title compound and present its crystal structure here. The title compound, which is shown in Fig.1, forms an extended one-dimensional chain structure arising from Sn—O bridges formed by the 1,1'-binaphthyl-2,2'-diyl phosphonate ligands. The Sn—O bond distances in the compound (Sn(1)—O(3) = 2.253 (3) Å; Sn(1)—O(4)#1 = 2.262 (3) Å; symmetry code (#1): #1 - x,y + 1/2,-z + 3/2) are comparable to those found in related organotin carboxylates (Ma et al. 2006, Wang et al. 2007). The Sn atom assumes a slightly distorted trigonal-bipyramidal coordination geometry, provided by and three methyl groups in the equatorial positions and two O atoms of symmetry related phosphate groups in the axial positions.

Related literature top

For the biological activity of organotin compounds, see: Dubey & Roy (2003). For related structures, see: Wang et al. (2007); Ma et al. (2006).

Experimental top

1,1'-Binaphthyl-2,2'-diyl phosphonate acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h under nitrogen. Trimethyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of diethyl ether to yield colourless blocks of the title compound (yield 83%). Anal. Calcd (%) for C₂₃H₂₁O₄P₁Sn₁ (Mr = 511.06): C, 54.05; H, 4.14. Found (%): C, 54.51; H, 4.64.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. A view of the one-dimensional extended chain structure in the title compound.

catena-Poly[[trimethyltin(IV)]-µ-(1,1'-binaphthyl-2,2'-diyl phosphonato)] top

Crystal data top

[Sn(CH₃)₃(C₂₀H₁₂O₄P)]	F(000) = 1024
M_r = 511.06	D_x = 1.535 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3010 reflections
a = 18.312 (2) Å	θ = 2.6–25.4°
b = 10.665 (2) Å	µ = 1.25 mm⁻¹
c = 11.3361 (18) Å	T = 298 K
β = 92.856 (2)°	Plate, colorless
V = 2211.2 (6) Å³	0.42 × 0.21 × 0.13 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	3892 independent reflections
Radiation source: fine-focus sealed tube	2695 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→19
T_min = 0.621, T_max = 0.854	k = −11→12
11194 measured reflections	l = −12→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0333P)² + 1.120P] where P = (F_o² + 2F_c²)/3
3892 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₂₀H₁₂O₄P)]	V = 2211.2 (6) Å³
M_r = 511.06	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.312 (2) Å	µ = 1.25 mm⁻¹
b = 10.665 (2) Å	T = 298 K
c = 11.3361 (18) Å	0.42 × 0.21 × 0.13 mm
β = 92.856 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3892 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2695 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.854	R_int = 0.050
11194 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.00	Δρ_max = 0.76 e Å⁻³
3892 reflections	Δρ_min = −0.55 e Å⁻³
262 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.023494 (17)	0.37358 (3)	0.73733 (3)	0.03206 (12)
O1	0.16136 (16)	0.0701 (3)	0.8547 (3)	0.0387 (8)
O2	0.18645 (16)	0.0599 (3)	0.6397 (3)	0.0366 (8)
O3	0.11465 (16)	0.2375 (3)	0.7063 (3)	0.0381 (8)
O4	0.05909 (17)	0.0202 (3)	0.7143 (3)	0.0447 (9)
P1	0.12454 (6)	0.10124 (12)	0.72665 (11)	0.0332 (3)
C1	0.2357 (3)	0.0974 (5)	0.8797 (4)	0.0412 (13)
C2	0.2521 (3)	0.1921 (5)	0.9613 (5)	0.0558 (16)
H2	0.2151	0.2343	0.9982	0.067*
C3	0.3238 (4)	0.2212 (6)	0.9858 (6)	0.074 (2)
H3	0.3357	0.2830	1.0414	0.088*
C4	0.3800 (4)	0.1599 (7)	0.9291 (6)	0.0705 (19)
C5	0.4550 (5)	0.1966 (8)	0.9479 (8)	0.106 (3)
H5	0.4676	0.2599	1.0016	0.127*
C6	0.5076 (4)	0.1390 (10)	0.8872 (10)	0.123 (4)
H6	0.5562	0.1634	0.8997	0.147*
C7	0.4903 (4)	0.0451 (9)	0.8073 (8)	0.105 (3)
H7	0.5273	0.0079	0.7663	0.126*
C8	0.4195 (3)	0.0051 (7)	0.7868 (6)	0.074 (2)
H8	0.4089	−0.0587	0.7327	0.088*
C9	0.3627 (3)	0.0616 (6)	0.8487 (5)	0.0541 (16)
C10	0.2878 (3)	0.0255 (5)	0.8278 (4)	0.0397 (13)
C11	0.2655 (2)	−0.0811 (5)	0.7489 (4)	0.0364 (12)
C12	0.2897 (3)	−0.2077 (5)	0.7690 (5)	0.0438 (13)
C13	0.3342 (3)	−0.2435 (6)	0.8696 (5)	0.0557 (16)
H13	0.3511	−0.1826	0.9230	0.067*
C14	0.3524 (3)	−0.3664 (7)	0.8891 (7)	0.077 (2)
H14	0.3805	−0.3886	0.9564	0.092*
C15	0.3290 (4)	−0.4585 (7)	0.8084 (8)	0.080 (2)
H15	0.3423	−0.5416	0.8219	0.096*
C16	0.2871 (3)	−0.4285 (6)	0.7108 (7)	0.0682 (19)
H16	0.2722	−0.4909	0.6576	0.082*
C17	0.2659 (3)	−0.3027 (5)	0.6891 (5)	0.0471 (14)
C18	0.2189 (3)	−0.2722 (5)	0.5902 (5)	0.0504 (15)
H18	0.2054	−0.3339	0.5354	0.060*
C19	0.1937 (3)	−0.1536 (5)	0.5750 (5)	0.0459 (14)
H19	0.1618	−0.1342	0.5112	0.055*
C20	0.2158 (2)	−0.0606 (5)	0.6556 (4)	0.0353 (12)
C21	0.0532 (3)	0.3602 (6)	0.9183 (4)	0.0700 (19)
H21A	0.1034	0.3844	0.9315	0.105*
H21B	0.0470	0.2754	0.9442	0.105*
H21C	0.0228	0.4148	0.9620	0.105*
C22	0.0762 (3)	0.5007 (5)	0.6267 (5)	0.0535 (15)
H22A	0.1202	0.5308	0.6666	0.080*
H22B	0.0443	0.5701	0.6081	0.080*
H22C	0.0881	0.4589	0.5551	0.080*
C23	−0.0628 (3)	0.2641 (5)	0.6592 (5)	0.0515 (15)
H23A	−0.0445	0.1828	0.6393	0.077*
H23B	−0.0821	0.3049	0.5889	0.077*
H23C	−0.1007	0.2550	0.7140	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0352 (2)	0.0324 (2)	0.02855 (18)	−0.00087 (18)	0.00089 (13)	0.00060 (16)
O1	0.038 (2)	0.045 (2)	0.0332 (19)	0.0040 (16)	0.0052 (15)	−0.0005 (16)
O2	0.0348 (19)	0.039 (2)	0.0361 (19)	0.0029 (16)	0.0061 (15)	−0.0013 (16)
O3	0.0366 (19)	0.034 (2)	0.044 (2)	0.0063 (16)	0.0054 (15)	0.0004 (16)
O4	0.0342 (19)	0.040 (2)	0.060 (2)	−0.0055 (17)	0.0056 (16)	0.0063 (18)
P1	0.0302 (7)	0.0349 (9)	0.0347 (7)	0.0007 (6)	0.0047 (5)	0.0000 (6)
C1	0.044 (3)	0.045 (4)	0.034 (3)	−0.003 (3)	−0.008 (2)	0.004 (2)
C2	0.071 (4)	0.047 (4)	0.048 (4)	0.008 (3)	−0.014 (3)	−0.006 (3)
C3	0.093 (5)	0.056 (5)	0.069 (4)	−0.011 (4)	−0.035 (4)	−0.010 (4)
C4	0.057 (4)	0.068 (5)	0.084 (5)	−0.015 (4)	−0.022 (4)	0.009 (4)
C5	0.078 (6)	0.101 (7)	0.133 (8)	−0.030 (5)	−0.041 (6)	−0.006 (6)
C6	0.050 (5)	0.144 (10)	0.170 (10)	−0.035 (6)	−0.023 (6)	0.021 (8)
C7	0.048 (5)	0.134 (9)	0.134 (8)	−0.013 (5)	0.000 (5)	0.009 (7)
C8	0.037 (4)	0.086 (6)	0.098 (5)	−0.004 (4)	0.003 (3)	0.013 (4)
C9	0.040 (3)	0.058 (4)	0.063 (4)	−0.006 (3)	−0.010 (3)	0.005 (3)
C10	0.033 (3)	0.045 (3)	0.040 (3)	0.000 (2)	−0.001 (2)	0.002 (3)
C11	0.025 (3)	0.041 (3)	0.044 (3)	0.002 (2)	0.010 (2)	−0.005 (2)
C12	0.038 (3)	0.041 (4)	0.054 (4)	0.005 (3)	0.015 (3)	−0.001 (3)
C13	0.045 (3)	0.062 (4)	0.060 (4)	0.013 (3)	0.008 (3)	0.008 (3)
C14	0.065 (4)	0.075 (6)	0.091 (5)	0.029 (4)	0.011 (4)	0.026 (5)
C15	0.068 (5)	0.050 (5)	0.124 (7)	0.017 (4)	0.028 (5)	0.016 (5)
C16	0.057 (4)	0.049 (4)	0.100 (6)	0.006 (3)	0.021 (4)	−0.007 (4)
C17	0.040 (3)	0.034 (3)	0.069 (4)	0.006 (3)	0.023 (3)	0.000 (3)
C18	0.044 (3)	0.046 (4)	0.062 (4)	−0.002 (3)	0.013 (3)	−0.015 (3)
C19	0.041 (3)	0.053 (4)	0.045 (3)	0.000 (3)	0.009 (2)	−0.012 (3)
C20	0.032 (3)	0.032 (3)	0.043 (3)	0.001 (2)	0.010 (2)	−0.004 (2)
C21	0.095 (5)	0.091 (5)	0.022 (3)	0.034 (4)	−0.006 (3)	−0.004 (3)
C22	0.057 (4)	0.042 (4)	0.063 (4)	−0.002 (3)	0.022 (3)	0.012 (3)
C23	0.051 (3)	0.045 (4)	0.058 (4)	−0.007 (3)	−0.006 (3)	−0.006 (3)

Geometric parameters (Å, º) top

Sn1—C21	2.101 (5)	C9—C10	1.432 (7)
Sn1—C22	2.113 (5)	C10—C11	1.491 (7)
Sn1—C23	2.123 (5)	C11—C20	1.378 (6)
Sn1—O3	2.253 (3)	C11—C12	1.436 (7)
Sn1—O4ⁱ	2.262 (3)	C12—C17	1.414 (7)
O1—C1	1.407 (5)	C12—C13	1.421 (7)
O1—P1	1.605 (3)	C13—C14	1.367 (8)
O2—C20	1.401 (6)	C13—H13	0.9300
O2—P1	1.601 (3)	C14—C15	1.396 (9)
O3—P1	1.481 (3)	C14—H14	0.9300
O4—P1	1.479 (3)	C15—C16	1.352 (9)
O4—Sn1ⁱⁱ	2.262 (3)	C15—H15	0.9300
C1—C10	1.379 (7)	C16—C17	1.415 (8)
C1—C2	1.392 (7)	C16—H16	0.9300
C2—C3	1.366 (8)	C17—C18	1.416 (7)
C2—H2	0.9300	C18—C19	1.356 (7)
C3—C4	1.402 (9)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.394 (7)
C4—C9	1.415 (9)	C19—H19	0.9300
C4—C5	1.434 (9)	C21—H21A	0.9600
C5—C6	1.358 (12)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.377 (12)	C22—H22A	0.9600
C6—H6	0.9300	C22—H22B	0.9600
C7—C8	1.373 (9)	C22—H22C	0.9600
C7—H7	0.9300	C23—H23A	0.9600
C8—C9	1.418 (8)	C23—H23B	0.9600
C8—H8	0.9300	C23—H23C	0.9600

C21—Sn1—C22	121.3 (2)	C9—C10—C11	122.4 (5)
C21—Sn1—C23	121.4 (2)	C20—C11—C12	117.2 (5)
C22—Sn1—C23	117.3 (2)	C20—C11—C10	119.4 (5)
C21—Sn1—O3	87.19 (17)	C12—C11—C10	123.3 (5)
C22—Sn1—O3	87.53 (17)	C17—C12—C13	117.9 (5)
C23—Sn1—O3	97.01 (17)	C17—C12—C11	119.3 (5)
C21—Sn1—O4ⁱ	87.34 (18)	C13—C12—C11	122.7 (5)
C22—Sn1—O4ⁱ	91.78 (17)	C14—C13—C12	120.9 (6)
C23—Sn1—O4ⁱ	89.37 (17)	C14—C13—H13	119.6
O3—Sn1—O4ⁱ	173.14 (12)	C12—C13—H13	119.6
C1—O1—P1	119.9 (3)	C13—C14—C15	120.3 (7)
C20—O2—P1	116.9 (3)	C13—C14—H14	119.8
P1—O3—Sn1	133.94 (18)	C15—C14—H14	119.8
P1—O4—Sn1ⁱⁱ	158.4 (2)	C16—C15—C14	120.8 (7)
O4—P1—O3	117.80 (19)	C16—C15—H15	119.6
O4—P1—O2	112.09 (19)	C14—C15—H15	119.6
O3—P1—O2	105.04 (18)	C15—C16—C17	120.4 (7)
O4—P1—O1	105.49 (19)	C15—C16—H16	119.8
O3—P1—O1	112.72 (19)	C17—C16—H16	119.8
O2—P1—O1	102.81 (17)	C12—C17—C16	119.7 (6)
C10—C1—C2	123.8 (5)	C12—C17—C18	119.9 (5)
C10—C1—O1	118.9 (4)	C16—C17—C18	120.4 (6)
C2—C1—O1	117.2 (5)	C19—C18—C17	120.3 (5)
C3—C2—C1	118.2 (6)	C19—C18—H18	119.8
C3—C2—H2	120.9	C17—C18—H18	119.8
C1—C2—H2	120.9	C18—C19—C20	119.6 (5)
C2—C3—C4	121.4 (6)	C18—C19—H19	120.2
C2—C3—H3	119.3	C20—C19—H19	120.2
C4—C3—H3	119.3	C11—C20—C19	123.3 (5)
C3—C4—C9	119.7 (6)	C11—C20—O2	118.6 (4)
C3—C4—C5	121.6 (7)	C19—C20—O2	118.1 (4)
C9—C4—C5	118.7 (7)	Sn1—C21—H21A	109.5
C6—C5—C4	120.0 (8)	Sn1—C21—H21B	109.5
C6—C5—H5	120.0	H21A—C21—H21B	109.5
C4—C5—H5	120.0	Sn1—C21—H21C	109.5
C5—C6—C7	121.1 (8)	H21A—C21—H21C	109.5
C5—C6—H6	119.5	H21B—C21—H21C	109.5
C7—C6—H6	119.5	Sn1—C22—H22A	109.5
C8—C7—C6	121.5 (8)	Sn1—C22—H22B	109.5
C8—C7—H7	119.3	H22A—C22—H22B	109.5
C6—C7—H7	119.3	Sn1—C22—H22C	109.5
C7—C8—C9	119.6 (7)	H22A—C22—H22C	109.5
C7—C8—H8	120.2	H22B—C22—H22C	109.5
C9—C8—H8	120.2	Sn1—C23—H23A	109.5
C4—C9—C8	119.2 (6)	Sn1—C23—H23B	109.5
C4—C9—C10	119.2 (6)	H23A—C23—H23B	109.5
C8—C9—C10	121.6 (6)	Sn1—C23—H23C	109.5
C1—C10—C9	117.2 (5)	H23A—C23—H23C	109.5
C1—C10—C11	120.3 (4)	H23B—C23—H23C	109.5

C21—Sn1—O3—P1	73.2 (3)	C2—C1—C10—C11	174.8 (5)
C22—Sn1—O3—P1	−165.3 (3)	O1—C1—C10—C11	−1.5 (7)
C23—Sn1—O3—P1	−48.1 (3)	C4—C9—C10—C1	5.8 (8)
O4ⁱ—Sn1—O3—P1	110.3 (10)	C8—C9—C10—C1	−171.2 (5)
Sn1ⁱⁱ—O4—P1—O3	−128.8 (5)	C4—C9—C10—C11	−177.0 (5)
Sn1ⁱⁱ—O4—P1—O2	109.1 (6)	C8—C9—C10—C11	6.0 (8)
Sn1ⁱⁱ—O4—P1—O1	−2.0 (6)	C1—C10—C11—C20	53.0 (7)
Sn1—O3—P1—O4	32.8 (4)	C9—C10—C11—C20	−124.1 (5)
Sn1—O3—P1—O2	158.4 (2)	C1—C10—C11—C12	−123.1 (5)
Sn1—O3—P1—O1	−90.5 (3)	C9—C10—C11—C12	59.9 (7)
C20—O2—P1—O4	−61.8 (4)	C20—C11—C12—C17	4.1 (7)
C20—O2—P1—O3	169.1 (3)	C10—C11—C12—C17	−179.8 (4)
C20—O2—P1—O1	51.0 (3)	C20—C11—C12—C13	−172.6 (4)
C1—O1—P1—O4	158.7 (4)	C10—C11—C12—C13	3.5 (7)
C1—O1—P1—O3	−71.5 (4)	C17—C12—C13—C14	−0.7 (8)
C1—O1—P1—O2	41.1 (4)	C11—C12—C13—C14	176.0 (5)
P1—O1—C1—C10	−71.3 (5)	C12—C13—C14—C15	1.6 (9)
P1—O1—C1—C2	112.1 (5)	C13—C14—C15—C16	−1.0 (10)
C10—C1—C2—C3	4.5 (9)	C14—C15—C16—C17	−0.4 (10)
O1—C1—C2—C3	−179.2 (5)	C13—C12—C17—C16	−0.6 (7)
C1—C2—C3—C4	1.3 (9)	C11—C12—C17—C16	−177.5 (5)
C2—C3—C4—C9	−3.0 (10)	C13—C12—C17—C18	177.3 (5)
C2—C3—C4—C5	175.2 (6)	C11—C12—C17—C18	0.5 (7)
C3—C4—C5—C6	−176.9 (8)	C15—C16—C17—C12	1.2 (8)
C9—C4—C5—C6	1.4 (12)	C15—C16—C17—C18	−176.7 (5)
C4—C5—C6—C7	−0.1 (15)	C12—C17—C18—C19	−3.5 (8)
C5—C6—C7—C8	−0.7 (15)	C16—C17—C18—C19	174.4 (5)
C6—C7—C8—C9	0.2 (12)	C17—C18—C19—C20	1.8 (8)
C3—C4—C9—C8	176.5 (6)	C12—C11—C20—C19	−6.1 (7)
C5—C4—C9—C8	−1.9 (9)	C10—C11—C20—C19	177.7 (4)
C3—C4—C9—C10	−0.6 (9)	C12—C11—C20—O2	174.8 (4)
C5—C4—C9—C10	−179.0 (6)	C10—C11—C20—O2	−1.5 (6)
C7—C8—C9—C4	1.1 (10)	C18—C19—C20—C11	3.2 (7)
C7—C8—C9—C10	178.1 (6)	C18—C19—C20—O2	−177.7 (4)
C2—C1—C10—C9	−8.0 (8)	P1—O2—C20—C11	−76.4 (5)
O1—C1—C10—C9	175.7 (4)	P1—O2—C20—C19	104.4 (4)

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

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₂₀H₁₂O₄P)]
M_r	511.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	18.312 (2), 10.665 (2), 11.3361 (18)
β (°)	92.856 (2)
V (Å³)	2211.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.42 × 0.21 × 0.13

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.621, 0.854
No. of measured, independent and observed [I > 2σ(I)] reflections	11194, 3892, 2695
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.085, 1.00
No. of reflections	3892
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.55

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—C21	2.101 (5)	Sn1—O3	2.253 (3)
Sn1—C22	2.113 (5)	Sn1—O4ⁱ	2.262 (3)
Sn1—C23	2.123 (5)

Symmetry code: (i) −x, y+1/2, −z+3/2.

Acknowledgements

We thank the National Natural Science Foundation of China (20971096) for financial support.

References

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