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Acta Cryst. (2010). E66, m63    [ doi:10.1107/S160053680905291X ]

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

J. Wu and R. Zhang

Abstract top

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.

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.

Refinement top

The H atoms were positioned geometrically, with methyl C—H distances of 0.96Å and aromatic C—H distances of 0.93 Å, and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(Caromatic) or 1.5 Ueq(C) for the methyl groups.

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
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] 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
Mr = 511.06Dx = 1.535 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3010 reflections
a = 18.312 (2) Åθ = 2.6–25.4°
b = 10.665 (2) ŵ = 1.25 mm−1
c = 11.3361 (18) ÅT = 298 K
β = 92.856 (2)°Plate, colorless
V = 2211.2 (6) Å30.42 × 0.21 × 0.13 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer		3892 independent reflections
Radiation source: fine-focus sealed tube2695 reflections with I > 2σ(I)
graphiteRint = 0.050
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −21→19
Tmin = 0.621, Tmax = 0.854k = −11→12
11194 measured reflectionsl = −12→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0333P)2 + 1.120P]
where P = (Fo2 + 2Fc2)/3
3892 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.76 e Å−3
0 restraintsΔρmin = −0.55 e Å−3
Crystal data top
[Sn(CH3)3(C20H12O4P)]V = 2211.2 (6) Å3
Mr = 511.06Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.312 (2) ŵ = 1.25 mm−1
b = 10.665 (2) ÅT = 298 K
c = 11.3361 (18) Å0.42 × 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)
Tmin = 0.621, Tmax = 0.854Rint = 0.050
11194 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.085Δρmax = 0.76 e Å−3
S = 1.00Δρmin = −0.55 e Å−3
3892 reflectionsAbsolute structure: ?
262 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.023494 (17)0.37358 (3)0.73733 (3)0.03206 (12)
O10.16136 (16)0.0701 (3)0.8547 (3)0.0387 (8)
O20.18645 (16)0.0599 (3)0.6397 (3)0.0366 (8)
O30.11465 (16)0.2375 (3)0.7063 (3)0.0381 (8)
O40.05909 (17)0.0202 (3)0.7143 (3)0.0447 (9)
P10.12454 (6)0.10124 (12)0.72665 (11)0.0332 (3)
C10.2357 (3)0.0974 (5)0.8797 (4)0.0412 (13)
C20.2521 (3)0.1921 (5)0.9613 (5)0.0558 (16)
H20.21510.23430.99820.067*
C30.3238 (4)0.2212 (6)0.9858 (6)0.074 (2)
H30.33570.28301.04140.088*
C40.3800 (4)0.1599 (7)0.9291 (6)0.0705 (19)
C50.4550 (5)0.1966 (8)0.9479 (8)0.106 (3)
H50.46760.25991.00160.127*
C60.5076 (4)0.1390 (10)0.8872 (10)0.123 (4)
H60.55620.16340.89970.147*
C70.4903 (4)0.0451 (9)0.8073 (8)0.105 (3)
H70.52730.00790.76630.126*
C80.4195 (3)0.0051 (7)0.7868 (6)0.074 (2)
H80.4089−0.05870.73270.088*
C90.3627 (3)0.0616 (6)0.8487 (5)0.0541 (16)
C100.2878 (3)0.0255 (5)0.8278 (4)0.0397 (13)
C110.2655 (2)−0.0811 (5)0.7489 (4)0.0364 (12)
C120.2897 (3)−0.2077 (5)0.7690 (5)0.0438 (13)
C130.3342 (3)−0.2435 (6)0.8696 (5)0.0557 (16)
H130.3511−0.18260.92300.067*
C140.3524 (3)−0.3664 (7)0.8891 (7)0.077 (2)
H140.3805−0.38860.95640.092*
C150.3290 (4)−0.4585 (7)0.8084 (8)0.080 (2)
H150.3423−0.54160.82190.096*
C160.2871 (3)−0.4285 (6)0.7108 (7)0.0682 (19)
H160.2722−0.49090.65760.082*
C170.2659 (3)−0.3027 (5)0.6891 (5)0.0471 (14)
C180.2189 (3)−0.2722 (5)0.5902 (5)0.0504 (15)
H180.2054−0.33390.53540.060*
C190.1937 (3)−0.1536 (5)0.5750 (5)0.0459 (14)
H190.1618−0.13420.51120.055*
C200.2158 (2)−0.0606 (5)0.6556 (4)0.0353 (12)
C210.0532 (3)0.3602 (6)0.9183 (4)0.0700 (19)
H21A0.10340.38440.93150.105*
H21B0.04700.27540.94420.105*
H21C0.02280.41480.96200.105*
C220.0762 (3)0.5007 (5)0.6267 (5)0.0535 (15)
H22A0.12020.53080.66660.080*
H22B0.04430.57010.60810.080*
H22C0.08810.45890.55510.080*
C23−0.0628 (3)0.2641 (5)0.6592 (5)0.0515 (15)
H23A−0.04450.18280.63930.077*
H23B−0.08210.30490.58890.077*
H23C−0.10070.25500.71400.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0352 (2)0.0324 (2)0.02855 (18)−0.00087 (18)0.00089 (13)0.00060 (16)
O10.038 (2)0.045 (2)0.0332 (19)0.0040 (16)0.0052 (15)−0.0005 (16)
O20.0348 (19)0.039 (2)0.0361 (19)0.0029 (16)0.0061 (15)−0.0013 (16)
O30.0366 (19)0.034 (2)0.044 (2)0.0063 (16)0.0054 (15)0.0004 (16)
O40.0342 (19)0.040 (2)0.060 (2)−0.0055 (17)0.0056 (16)0.0063 (18)
P10.0302 (7)0.0349 (9)0.0347 (7)0.0007 (6)0.0047 (5)0.0000 (6)
C10.044 (3)0.045 (4)0.034 (3)−0.003 (3)−0.008 (2)0.004 (2)
C20.071 (4)0.047 (4)0.048 (4)0.008 (3)−0.014 (3)−0.006 (3)
C30.093 (5)0.056 (5)0.069 (4)−0.011 (4)−0.035 (4)−0.010 (4)
C40.057 (4)0.068 (5)0.084 (5)−0.015 (4)−0.022 (4)0.009 (4)
C50.078 (6)0.101 (7)0.133 (8)−0.030 (5)−0.041 (6)−0.006 (6)
C60.050 (5)0.144 (10)0.170 (10)−0.035 (6)−0.023 (6)0.021 (8)
C70.048 (5)0.134 (9)0.134 (8)−0.013 (5)0.000 (5)0.009 (7)
C80.037 (4)0.086 (6)0.098 (5)−0.004 (4)0.003 (3)0.013 (4)
C90.040 (3)0.058 (4)0.063 (4)−0.006 (3)−0.010 (3)0.005 (3)
C100.033 (3)0.045 (3)0.040 (3)0.000 (2)−0.001 (2)0.002 (3)
C110.025 (3)0.041 (3)0.044 (3)0.002 (2)0.010 (2)−0.005 (2)
C120.038 (3)0.041 (4)0.054 (4)0.005 (3)0.015 (3)−0.001 (3)
C130.045 (3)0.062 (4)0.060 (4)0.013 (3)0.008 (3)0.008 (3)
C140.065 (4)0.075 (6)0.091 (5)0.029 (4)0.011 (4)0.026 (5)
C150.068 (5)0.050 (5)0.124 (7)0.017 (4)0.028 (5)0.016 (5)
C160.057 (4)0.049 (4)0.100 (6)0.006 (3)0.021 (4)−0.007 (4)
C170.040 (3)0.034 (3)0.069 (4)0.006 (3)0.023 (3)0.000 (3)
C180.044 (3)0.046 (4)0.062 (4)−0.002 (3)0.013 (3)−0.015 (3)
C190.041 (3)0.053 (4)0.045 (3)0.000 (3)0.009 (2)−0.012 (3)
C200.032 (3)0.032 (3)0.043 (3)0.001 (2)0.010 (2)−0.004 (2)
C210.095 (5)0.091 (5)0.022 (3)0.034 (4)−0.006 (3)−0.004 (3)
C220.057 (4)0.042 (4)0.063 (4)−0.002 (3)0.022 (3)0.012 (3)
C230.051 (3)0.045 (4)0.058 (4)−0.007 (3)−0.006 (3)−0.006 (3)
Geometric parameters (Å, °) top
Sn1—C212.101 (5)C9—C101.432 (7)
Sn1—C222.113 (5)C10—C111.491 (7)
Sn1—C232.123 (5)C11—C201.378 (6)
Sn1—O32.253 (3)C11—C121.436 (7)
Sn1—O4i2.262 (3)C12—C171.414 (7)
O1—C11.407 (5)C12—C131.421 (7)
O1—P11.605 (3)C13—C141.367 (8)
O2—C201.401 (6)C13—H130.9300
O2—P11.601 (3)C14—C151.396 (9)
O3—P11.481 (3)C14—H140.9300
O4—P11.479 (3)C15—C161.352 (9)
O4—Sn1ii2.262 (3)C15—H150.9300
C1—C101.379 (7)C16—C171.415 (8)
C1—C21.392 (7)C16—H160.9300
C2—C31.366 (8)C17—C181.416 (7)
C2—H20.9300C18—C191.356 (7)
C3—C41.402 (9)C18—H180.9300
C3—H30.9300C19—C201.394 (7)
C4—C91.415 (9)C19—H190.9300
C4—C51.434 (9)C21—H21A0.9600
C5—C61.358 (12)C21—H21B0.9600
C5—H50.9300C21—H21C0.9600
C6—C71.377 (12)C22—H22A0.9600
C6—H60.9300C22—H22B0.9600
C7—C81.373 (9)C22—H22C0.9600
C7—H70.9300C23—H23A0.9600
C8—C91.418 (8)C23—H23B0.9600
C8—H80.9300C23—H23C0.9600
C21—Sn1—C22121.3 (2)C9—C10—C11122.4 (5)
C21—Sn1—C23121.4 (2)C20—C11—C12117.2 (5)
C22—Sn1—C23117.3 (2)C20—C11—C10119.4 (5)
C21—Sn1—O387.19 (17)C12—C11—C10123.3 (5)
C22—Sn1—O387.53 (17)C17—C12—C13117.9 (5)
C23—Sn1—O397.01 (17)C17—C12—C11119.3 (5)
C21—Sn1—O4i87.34 (18)C13—C12—C11122.7 (5)
C22—Sn1—O4i91.78 (17)C14—C13—C12120.9 (6)
C23—Sn1—O4i89.37 (17)C14—C13—H13119.6
O3—Sn1—O4i173.14 (12)C12—C13—H13119.6
C1—O1—P1119.9 (3)C13—C14—C15120.3 (7)
C20—O2—P1116.9 (3)C13—C14—H14119.8
P1—O3—Sn1133.94 (18)C15—C14—H14119.8
P1—O4—Sn1ii158.4 (2)C16—C15—C14120.8 (7)
O4—P1—O3117.80 (19)C16—C15—H15119.6
O4—P1—O2112.09 (19)C14—C15—H15119.6
O3—P1—O2105.04 (18)C15—C16—C17120.4 (7)
O4—P1—O1105.49 (19)C15—C16—H16119.8
O3—P1—O1112.72 (19)C17—C16—H16119.8
O2—P1—O1102.81 (17)C12—C17—C16119.7 (6)
C10—C1—C2123.8 (5)C12—C17—C18119.9 (5)
C10—C1—O1118.9 (4)C16—C17—C18120.4 (6)
C2—C1—O1117.2 (5)C19—C18—C17120.3 (5)
C3—C2—C1118.2 (6)C19—C18—H18119.8
C3—C2—H2120.9C17—C18—H18119.8
C1—C2—H2120.9C18—C19—C20119.6 (5)
C2—C3—C4121.4 (6)C18—C19—H19120.2
C2—C3—H3119.3C20—C19—H19120.2
C4—C3—H3119.3C11—C20—C19123.3 (5)
C3—C4—C9119.7 (6)C11—C20—O2118.6 (4)
C3—C4—C5121.6 (7)C19—C20—O2118.1 (4)
C9—C4—C5118.7 (7)Sn1—C21—H21A109.5
C6—C5—C4120.0 (8)Sn1—C21—H21B109.5
C6—C5—H5120.0H21A—C21—H21B109.5
C4—C5—H5120.0Sn1—C21—H21C109.5
C5—C6—C7121.1 (8)H21A—C21—H21C109.5
C5—C6—H6119.5H21B—C21—H21C109.5
C7—C6—H6119.5Sn1—C22—H22A109.5
C8—C7—C6121.5 (8)Sn1—C22—H22B109.5
C8—C7—H7119.3H22A—C22—H22B109.5
C6—C7—H7119.3Sn1—C22—H22C109.5
C7—C8—C9119.6 (7)H22A—C22—H22C109.5
C7—C8—H8120.2H22B—C22—H22C109.5
C9—C8—H8120.2Sn1—C23—H23A109.5
C4—C9—C8119.2 (6)Sn1—C23—H23B109.5
C4—C9—C10119.2 (6)H23A—C23—H23B109.5
C8—C9—C10121.6 (6)Sn1—C23—H23C109.5
C1—C10—C9117.2 (5)H23A—C23—H23C109.5
C1—C10—C11120.3 (4)H23B—C23—H23C109.5
C21—Sn1—O3—P173.2 (3)C2—C1—C10—C11174.8 (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—C15.8 (8)
O4i—Sn1—O3—P1110.3 (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—O2109.1 (6)C8—C9—C10—C116.0 (8)
Sn1ii—O4—P1—O1−2.0 (6)C1—C10—C11—C2053.0 (7)
Sn1—O3—P1—O432.8 (4)C9—C10—C11—C20−124.1 (5)
Sn1—O3—P1—O2158.4 (2)C1—C10—C11—C12−123.1 (5)
Sn1—O3—P1—O1−90.5 (3)C9—C10—C11—C1259.9 (7)
C20—O2—P1—O4−61.8 (4)C20—C11—C12—C174.1 (7)
C20—O2—P1—O3169.1 (3)C10—C11—C12—C17−179.8 (4)
C20—O2—P1—O151.0 (3)C20—C11—C12—C13−172.6 (4)
C1—O1—P1—O4158.7 (4)C10—C11—C12—C133.5 (7)
C1—O1—P1—O3−71.5 (4)C17—C12—C13—C14−0.7 (8)
C1—O1—P1—O241.1 (4)C11—C12—C13—C14176.0 (5)
P1—O1—C1—C10−71.3 (5)C12—C13—C14—C151.6 (9)
P1—O1—C1—C2112.1 (5)C13—C14—C15—C16−1.0 (10)
C10—C1—C2—C34.5 (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—C41.3 (9)C11—C12—C17—C16−177.5 (5)
C2—C3—C4—C9−3.0 (10)C13—C12—C17—C18177.3 (5)
C2—C3—C4—C5175.2 (6)C11—C12—C17—C180.5 (7)
C3—C4—C5—C6−176.9 (8)C15—C16—C17—C121.2 (8)
C9—C4—C5—C61.4 (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—C19174.4 (5)
C6—C7—C8—C90.2 (12)C17—C18—C19—C201.8 (8)
C3—C4—C9—C8176.5 (6)C12—C11—C20—C19−6.1 (7)
C5—C4—C9—C8−1.9 (9)C10—C11—C20—C19177.7 (4)
C3—C4—C9—C10−0.6 (9)C12—C11—C20—O2174.8 (4)
C5—C4—C9—C10−179.0 (6)C10—C11—C20—O2−1.5 (6)
C7—C8—C9—C41.1 (10)C18—C19—C20—C113.2 (7)
C7—C8—C9—C10178.1 (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—C9175.7 (4)P1—O2—C20—C19104.4 (4)
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x, y−1/2, −z+3/2.
Table 1
Selected geometric parameters (Å) top
Sn1—C212.101 (5)Sn1—O32.253 (3)
Sn1—C222.113 (5)Sn1—O4i2.262 (3)
Sn1—C232.123 (5)
Symmetry codes: (i) −x, y+1/2, −z+3/2.
Acknowledgements top

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

references
References top

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Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA.

Wang, H., Yin, H. & Wang, D. (2007). Acta Cryst. E63, m2955.