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The title compound, [Sn(C6H5)(C8H7O3)2(C4H11Si)], was prepared by the reaction of [(CH3)3SiCH2]SnPhBr2 with CH3OC6H5COOH and spasmolytol in refluxing toluene, and characterized by IR, 1H NMR and elemental analyses. The geometry at the six-coordinate SnIV atom is distorted octa­hedral with the equatorial plane made up of four O atoms of two carboxyl­ate groups and the axial positions occupied by a phen­yl substituent and a trimethyl­silylmeth­yl group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015370/ci6580sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015370/ci6580Isup2.hkl
Contains datablock I

CCDC reference: 274369

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.030
  • wR factor = 0.091
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Si1
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O2 .. 7.77 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O5 .. 7.99 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; molecular graphics: APEX2; software used to prepare material for publication: APEX2.

Bis(4-methoxylbenzoato)phenyl(trimethylsilylmethyl)tin(IV) top
Crystal data top
[Sn(C6H5)(C8H7O3)2(C4H11Si)]F(000) = 1192
Mr = 585.28Dx = 1.426 Mg m3
Monoclinic, P21/cMelting point: 410.5 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 20.1618 (4) ÅCell parameters from 6030 reflections
b = 11.9426 (3) Åθ = 2.5–25.2°
c = 11.3334 (2) ŵ = 1.02 mm1
β = 92.080 (1)°T = 273 K
V = 2727.11 (10) Å3Block, colourless
Z = 40.28 × 0.28 × 0.27 mm
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
4235 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 26.0°, θmin = 2.5°
φ and ω scansh = 2424
26340 measured reflectionsk = 1414
5315 independent reflectionsl = 1313
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.062P)2]
where P = (Fo2 + 2Fc2)/3
5315 reflections(Δ/σ)max = 0.003
312 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.60 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.33908 (13)0.5233 (2)0.9626 (2)0.0485 (6)
C20.37880 (13)0.4332 (2)0.9104 (2)0.0465 (6)
C30.43602 (14)0.3961 (2)0.9697 (3)0.0556 (7)
H30.44850.42781.04210.067*
C40.47465 (15)0.3130 (2)0.9231 (3)0.0607 (8)
H40.51220.28750.96480.073*
C50.45739 (13)0.2682 (2)0.8147 (3)0.0520 (6)
C60.40054 (16)0.3049 (3)0.7537 (3)0.0645 (8)
H60.38870.27450.68040.077*
C70.36176 (14)0.3863 (3)0.8017 (3)0.0563 (7)
H70.32350.41020.76080.068*
C80.5471 (2)0.1377 (4)0.8228 (4)0.0975 (13)
H8A0.58000.19430.83890.146*
H8B0.56570.07950.77600.146*
H8C0.53280.10680.89580.146*
C90.13024 (13)0.7554 (2)0.9466 (2)0.0459 (6)
C100.06566 (12)0.7856 (2)0.8896 (2)0.0431 (6)
C110.04837 (14)0.7526 (3)0.7749 (2)0.0565 (7)
H110.07740.70860.73280.068*
C120.01179 (16)0.7848 (3)0.7231 (3)0.0629 (8)
H120.02300.76310.64620.075*
C130.05556 (14)0.8498 (2)0.7862 (3)0.0519 (7)
C140.03879 (13)0.8821 (2)0.8995 (2)0.0491 (6)
H140.06820.92460.94240.059*
C150.02208 (13)0.8514 (2)0.9498 (3)0.0476 (6)
H150.03380.87551.02570.057*
C160.15846 (15)0.9489 (3)0.7842 (3)0.0722 (9)
H16A0.17140.91570.85690.108*
H16B0.19700.96030.73340.108*
H16C0.13731.01960.80020.108*
C170.30332 (14)0.8173 (2)0.9783 (3)0.0510 (7)
C180.35383 (17)0.8082 (3)0.8972 (3)0.0669 (9)
H180.36490.73850.86730.080*
C190.38711 (19)0.9026 (4)0.8616 (4)0.0891 (12)
H190.42020.89610.80680.107*
C200.3721 (2)1.0056 (4)0.9057 (4)0.0944 (13)
H200.39481.06870.88110.113*
C210.3231 (2)1.0154 (3)0.9870 (4)0.0871 (11)
H210.31311.08531.01800.105*
C220.28888 (16)0.9216 (3)1.0226 (3)0.0672 (8)
H220.25570.92901.07700.081*
C230.21750 (14)0.5964 (2)1.1767 (3)0.0556 (7)
H23A0.25700.58521.22670.067*
H23B0.18970.64911.21710.067*
C240.2255 (3)0.3501 (3)1.1061 (6)0.125 (2)
H24A0.20330.27911.10830.188*
H24B0.26650.34581.15170.188*
H24C0.23450.36861.02590.188*
C250.1527 (2)0.4224 (4)1.3242 (3)0.0947 (13)
H25A0.11070.45421.34330.142*
H25B0.18680.45151.37700.142*
H25C0.15080.34241.33200.142*
C260.0940 (2)0.4719 (4)1.0774 (4)0.1010 (14)
H26A0.10350.50441.00250.152*
H26B0.06320.51871.11720.152*
H26C0.07500.39891.06540.152*
O10.28392 (9)0.55218 (16)0.90642 (17)0.0527 (5)
O20.35620 (10)0.57121 (17)1.05459 (18)0.0600 (5)
O30.49196 (13)0.18588 (19)0.7602 (2)0.0720 (7)
O40.16692 (9)0.68110 (15)0.89651 (18)0.0506 (5)
O50.15031 (10)0.79847 (17)1.04125 (18)0.0547 (5)
O60.11322 (10)0.8762 (2)0.72747 (19)0.0698 (6)
Si10.17195 (5)0.45953 (7)1.16885 (8)0.0623 (2)
Sn10.247341 (8)0.674189 (15)1.020866 (17)0.04409 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0397 (14)0.0515 (15)0.0547 (16)0.0016 (12)0.0064 (11)0.0031 (12)
C20.0369 (14)0.0444 (14)0.0583 (16)0.0004 (11)0.0026 (11)0.0038 (12)
C30.0482 (16)0.0619 (18)0.0563 (17)0.0053 (13)0.0046 (13)0.0060 (13)
C40.0442 (16)0.0679 (19)0.069 (2)0.0145 (13)0.0069 (14)0.0023 (14)
C50.0418 (15)0.0508 (16)0.0638 (18)0.0072 (12)0.0086 (12)0.0006 (13)
C60.0595 (19)0.069 (2)0.064 (2)0.0124 (15)0.0080 (15)0.0149 (15)
C70.0418 (15)0.0656 (19)0.0608 (18)0.0146 (13)0.0084 (12)0.0071 (14)
C80.081 (3)0.113 (3)0.099 (3)0.054 (2)0.006 (2)0.002 (3)
C90.0402 (14)0.0481 (15)0.0499 (15)0.0028 (11)0.0074 (11)0.0039 (11)
C100.0335 (13)0.0460 (14)0.0500 (15)0.0003 (11)0.0051 (10)0.0019 (11)
C110.0439 (15)0.0681 (19)0.0578 (17)0.0105 (13)0.0069 (12)0.0111 (14)
C120.0542 (18)0.085 (2)0.0488 (18)0.0134 (16)0.0000 (13)0.0132 (15)
C130.0375 (15)0.0576 (17)0.0606 (18)0.0065 (12)0.0034 (12)0.0021 (13)
C140.0414 (14)0.0498 (15)0.0567 (16)0.0084 (12)0.0102 (12)0.0019 (12)
C150.0445 (15)0.0516 (15)0.0470 (15)0.0003 (11)0.0057 (11)0.0025 (11)
C160.0451 (17)0.073 (2)0.098 (3)0.0195 (15)0.0031 (16)0.0077 (18)
C170.0389 (15)0.0563 (17)0.0576 (18)0.0040 (12)0.0031 (12)0.0035 (12)
C180.057 (2)0.077 (2)0.068 (2)0.0058 (16)0.0136 (16)0.0062 (16)
C190.069 (2)0.105 (3)0.094 (3)0.020 (2)0.017 (2)0.024 (2)
C200.084 (3)0.083 (3)0.115 (3)0.034 (2)0.012 (2)0.033 (2)
C210.087 (3)0.053 (2)0.120 (3)0.0139 (18)0.009 (2)0.001 (2)
C220.0553 (18)0.0583 (19)0.088 (2)0.0029 (15)0.0038 (16)0.0090 (16)
C230.0539 (17)0.0604 (17)0.0527 (16)0.0011 (14)0.0038 (13)0.0017 (13)
C240.144 (5)0.063 (3)0.173 (6)0.006 (3)0.073 (4)0.006 (3)
C250.117 (3)0.095 (3)0.074 (2)0.035 (2)0.018 (2)0.010 (2)
C260.089 (3)0.109 (3)0.104 (3)0.033 (3)0.015 (2)0.004 (3)
O10.0399 (10)0.0586 (11)0.0593 (11)0.0086 (8)0.0003 (8)0.0078 (9)
O20.0528 (12)0.0647 (12)0.0620 (12)0.0086 (10)0.0045 (9)0.0116 (10)
O30.0621 (15)0.0751 (15)0.0788 (16)0.0268 (11)0.0033 (12)0.0130 (11)
O40.0372 (10)0.0570 (12)0.0573 (12)0.0065 (8)0.0006 (8)0.0047 (8)
O50.0423 (11)0.0665 (12)0.0553 (12)0.0011 (9)0.0001 (9)0.0088 (9)
O60.0489 (12)0.0919 (16)0.0681 (14)0.0186 (11)0.0067 (10)0.0050 (12)
Si10.0661 (5)0.0561 (5)0.0655 (5)0.0079 (4)0.0139 (4)0.0015 (4)
Sn10.03639 (13)0.04669 (13)0.04925 (14)0.00023 (7)0.00240 (8)0.00183 (7)
Geometric parameters (Å, º) top
C1—O21.228 (3)C16—H16B0.96
C1—O11.307 (3)C16—H16C0.96
C1—C21.477 (4)C17—C221.377 (4)
C2—C71.384 (4)C17—C181.401 (5)
C2—C31.387 (4)C17—Sn12.114 (3)
C3—C41.378 (4)C18—C191.380 (5)
C3—H30.93C18—H180.93
C4—C51.373 (4)C19—C201.365 (6)
C4—H40.93C19—H190.93
C5—O31.365 (3)C20—C211.380 (6)
C5—C61.388 (4)C20—H200.93
C6—C71.372 (4)C21—C221.384 (5)
C6—H60.93C21—H210.93
C7—H70.93C22—H220.93
C8—O31.418 (4)C23—Si11.875 (3)
C8—H8A0.96C23—Sn12.103 (3)
C8—H8B0.96C23—H23A0.97
C8—H8C0.96C23—H23B0.97
C9—O51.244 (3)C24—Si11.854 (5)
C9—O41.299 (3)C24—H24A0.96
C9—C101.477 (4)C24—H24B0.96
C10—C151.378 (4)C24—H24C0.96
C10—C111.390 (4)C25—Si11.869 (4)
C11—C121.383 (4)C25—H25A0.96
C11—H110.93C25—H25B0.96
C12—C131.392 (4)C25—H25C0.96
C12—H120.93C26—Si11.857 (4)
C13—O61.356 (3)C26—H26A0.96
C13—C141.371 (4)C26—H26B0.96
C14—C151.384 (4)C26—H26C0.96
C14—H140.93O1—Sn12.1021 (18)
C15—H150.93O2—Sn12.5328 (19)
C16—O61.429 (4)O4—Sn12.1109 (18)
C16—H16A0.96O5—Sn12.473 (2)
O2—C1—O1119.9 (3)C18—C19—H19119.6
O2—C1—C2122.7 (2)C19—C20—C21119.7 (4)
O1—C1—C2117.5 (2)C19—C20—H20120.1
C7—C2—C3118.5 (3)C21—C20—H20120.1
C7—C2—C1122.0 (2)C20—C21—C22120.1 (4)
C3—C2—C1119.5 (3)C20—C21—H21119.9
C4—C3—C2121.0 (3)C22—C21—H21119.9
C4—C3—H3119.5C17—C22—C21120.8 (3)
C2—C3—H3119.5C17—C22—H22119.6
C5—C4—C3119.7 (3)C21—C22—H22119.6
C5—C4—H4120.2Si1—C23—Sn1120.00 (15)
C3—C4—H4120.2Si1—C23—H23A107.3
O3—C5—C4124.7 (3)Sn1—C23—H23A107.3
O3—C5—C6115.4 (3)Si1—C23—H23B107.3
C4—C5—C6120.0 (3)Sn1—C23—H23B107.3
C7—C6—C5119.9 (3)H23A—C23—H23B106.9
C7—C6—H6120.0Si1—C24—H24A109.5
C5—C6—H6120.0Si1—C24—H24B109.5
C6—C7—C2120.8 (3)H24A—C24—H24B109.5
C6—C7—H7119.6Si1—C24—H24C109.5
C2—C7—H7119.6H24A—C24—H24C109.5
O3—C8—H8A109.5H24B—C24—H24C109.5
O3—C8—H8B109.5Si1—C25—H25A109.5
H8A—C8—H8B109.5Si1—C25—H25B109.5
O3—C8—H8C109.5H25A—C25—H25B109.5
H8A—C8—H8C109.5Si1—C25—H25C109.5
H8B—C8—H8C109.5H25A—C25—H25C109.5
O5—C9—O4119.1 (2)H25B—C25—H25C109.5
O5—C9—C10122.0 (2)Si1—C26—H26A109.5
O4—C9—C10118.8 (2)Si1—C26—H26B109.5
C15—C10—C11118.8 (2)H26A—C26—H26B109.5
C15—C10—C9119.3 (2)Si1—C26—H26C109.5
C11—C10—C9121.8 (2)H26A—C26—H26C109.5
C12—C11—C10120.3 (3)H26B—C26—H26C109.5
C12—C11—H11119.9C1—O1—Sn1101.19 (16)
C10—C11—H11119.9C1—O2—Sn183.27 (16)
C11—C12—C13120.0 (3)C5—O3—C8118.0 (3)
C11—C12—H12120.0C9—O4—Sn199.83 (16)
C13—C12—H12120.0C9—O5—Sn184.55 (16)
O6—C13—C14124.9 (3)C13—O6—C16118.1 (3)
O6—C13—C12115.2 (3)C24—Si1—C26109.6 (3)
C14—C13—C12119.9 (3)C24—Si1—C25109.7 (2)
C13—C14—C15119.7 (3)C26—Si1—C25110.1 (2)
C13—C14—H14120.1C24—Si1—C23109.97 (19)
C15—C14—H14120.1C26—Si1—C23111.12 (17)
C10—C15—C14121.3 (3)C25—Si1—C23106.26 (16)
C10—C15—H15119.4O1—Sn1—C23109.23 (10)
C14—C15—H15119.4O1—Sn1—O483.88 (7)
O6—C16—H16A109.5C23—Sn1—O4109.98 (10)
O6—C16—H16B109.5O1—Sn1—C17102.57 (10)
H16A—C16—H16B109.5C23—Sn1—C17136.08 (12)
O6—C16—H16C109.5O4—Sn1—C17102.69 (9)
H16A—C16—H16C109.5O1—Sn1—O5140.36 (7)
H16B—C16—H16C109.5C23—Sn1—O586.29 (10)
C22—C17—C18118.5 (3)O4—Sn1—O556.49 (7)
C22—C17—Sn1121.7 (2)C17—Sn1—O588.09 (9)
C18—C17—Sn1119.6 (2)O1—Sn1—O255.60 (6)
C19—C18—C17120.1 (4)C23—Sn1—O286.07 (10)
C19—C18—H18120.0O4—Sn1—O2139.47 (7)
C17—C18—H18120.0C17—Sn1—O287.71 (9)
C20—C19—C18120.8 (4)O5—Sn1—O2164.03 (6)
C20—C19—H19119.6
 

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