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The title compound, [Sn(C4H9)3(C7H9O2)]n, forms a polymeric chain involving both O atoms of the carboxyl­ate group. The Sn atom is five-coordinate and shows a distorted trigonal–bipyramidal geometry wherein the Cα atoms of the n-butyl chains occupy the equatorial positions. Two O atoms from symmetry-related ligands are asymmetrically bonded to the Sn atom and occupy axial positions with significantly different Sn—O distances of 2.209 (2) and 2.358 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015194/tk2035sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015194/tk2035Isup2.hkl
Contains datablock I

CCDC reference: 610913

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.028
  • wR factor = 0.062
  • Data-to-parameter ratio = 23.6

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.26 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 68.00 A   3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 4776 Count of symmetry unique reflns 2581 Completeness (_total/calc) 185.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2195 Fraction of Friedel pairs measured 0.850 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

catena-Poly[-tri-n-butyltin(IV)]-µ-cyclopent-2-enylacetato-κ2O:O'] top
Crystal data top
[Sn(C4H9)3(C7H9O2)]Dx = 1.298 Mg m3
Mr = 415.17Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4Cell parameters from 8643 reflections
Hall symbol: I -4θ = 3.1–27.5°
a = 20.559 (6) ŵ = 1.21 mm1
c = 10.053 (7) ÅT = 173 K
V = 4249 (3) Å3Block, colorless
Z = 80.20 × 0.10 × 0.09 mm
F(000) = 1728
Data collection top
Nonius KappaCCD
diffractometer
4776 independent reflections
Radiation source: fine-focus sealed tube4277 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω and φ scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 2626
Tmin = 0.794, Tmax = 0.899k = 2626
8643 measured reflectionsl = 1311
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.062 w = 1/[σ2(Fo2) + (0.024P)2 + 2.15P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4776 reflectionsΔρmax = 0.41 e Å3
202 parametersΔρmin = 0.42 e Å3
0 restraintsAbsolute structure: Flack (1983), 2195 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.729934 (11)0.780975 (11)0.408215 (19)0.03244 (7)
O10.67822 (11)0.83328 (11)0.56837 (19)0.0378 (5)
O20.72512 (12)0.77096 (11)0.72034 (19)0.0407 (5)
C10.6802 (2)0.69231 (18)0.4496 (4)0.0454 (9)
H1A0.70880.65550.42490.054*
H1B0.67220.68960.54660.054*
C20.61525 (19)0.6849 (2)0.3767 (4)0.0516 (10)
H2A0.58770.72330.39600.062*
H2B0.62350.68410.27970.062*
C30.5791 (2)0.6247 (2)0.4151 (5)0.0632 (11)
H3A0.57170.62530.51240.076*
H3B0.60640.58640.39430.076*
C40.5143 (2)0.6173 (3)0.3456 (5)0.0867 (17)
H4A0.49490.57540.36970.104*
H4B0.52080.61920.24910.104*
H4C0.48520.65270.37300.104*
C50.6876 (2)0.84172 (19)0.2577 (3)0.0487 (9)
H5A0.72180.85160.19140.058*
H5B0.65360.81600.21160.058*
C60.6577 (2)0.90486 (19)0.3001 (4)0.0539 (10)
H6A0.62510.89590.37030.065*
H6B0.63430.92380.22320.065*
C70.7055 (2)0.9547 (2)0.3521 (4)0.0640 (12)
H7A0.73010.93630.42790.077*
H7B0.73690.96640.28130.077*
C80.6690 (3)1.0146 (3)0.3962 (7)0.108 (2)
H8A0.69961.04590.43480.130*
H8B0.63651.00240.46300.130*
H8C0.64721.03430.31940.130*
C90.82564 (16)0.80398 (18)0.4795 (3)0.0381 (8)
H9A0.82110.83230.55860.046*
H9B0.84660.76310.50900.046*
C100.87062 (17)0.8372 (2)0.3824 (4)0.0485 (10)
H10A0.85150.87960.35670.058*
H10B0.87400.81030.30100.058*
C110.93879 (19)0.8486 (2)0.4379 (5)0.0595 (12)
H11A0.93500.87280.52260.071*
H11B0.95870.80590.45830.071*
C120.9833 (3)0.8851 (3)0.3474 (6)0.0891 (18)
H12A1.02640.88870.38870.107*
H12B0.96570.92870.33160.107*
H12C0.98710.86190.26260.107*
C130.68787 (16)0.81645 (16)0.6891 (3)0.0337 (7)
C140.65064 (18)0.85365 (16)0.7943 (3)0.0400 (8)
H14A0.67250.84780.88130.048*
H14B0.60630.83530.80160.048*
C150.6458 (2)0.92648 (18)0.7637 (4)0.0498 (9)
H150.62290.93340.67700.060*
C160.6115 (3)0.9642 (3)0.8745 (5)0.0798 (17)
H16A0.57860.99410.83640.096*
H16B0.58930.93380.93600.096*
C170.6608 (4)1.0005 (3)0.9441 (5)0.110 (3)
H17A0.64711.04650.95170.132*
H17B0.66590.98281.03510.132*
C180.7220 (3)0.9969 (3)0.8750 (6)0.0920 (17)
H180.76171.01660.90190.110*
C190.7123 (2)0.9594 (2)0.7615 (5)0.0627 (12)
H190.74320.95490.69170.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03661 (14)0.03573 (14)0.02497 (9)0.00165 (11)0.00274 (10)0.00074 (10)
O10.0439 (13)0.0432 (13)0.0264 (11)0.0080 (10)0.0043 (9)0.0016 (9)
O20.0509 (16)0.0404 (15)0.0310 (9)0.0099 (13)0.0018 (12)0.0038 (10)
C10.055 (2)0.038 (2)0.044 (2)0.0097 (17)0.0046 (17)0.0037 (15)
C20.051 (2)0.065 (3)0.039 (2)0.012 (2)0.0041 (16)0.0017 (17)
C30.070 (3)0.067 (3)0.053 (2)0.019 (2)0.016 (2)0.010 (2)
C40.061 (3)0.131 (5)0.068 (3)0.033 (3)0.003 (3)0.007 (3)
C50.060 (3)0.050 (2)0.0366 (18)0.009 (2)0.0134 (17)0.0037 (16)
C60.057 (3)0.057 (3)0.048 (2)0.003 (2)0.0066 (18)0.0098 (19)
C70.087 (3)0.044 (2)0.061 (3)0.012 (2)0.022 (2)0.013 (2)
C80.147 (6)0.072 (4)0.105 (5)0.010 (4)0.045 (5)0.009 (4)
C90.0353 (19)0.048 (2)0.0307 (16)0.0016 (16)0.0025 (14)0.0039 (15)
C100.040 (2)0.060 (2)0.046 (2)0.0054 (18)0.0055 (16)0.0074 (18)
C110.043 (2)0.068 (3)0.068 (3)0.009 (2)0.004 (2)0.005 (2)
C120.061 (3)0.094 (4)0.112 (4)0.026 (3)0.006 (3)0.031 (3)
C130.0393 (18)0.0328 (17)0.0290 (15)0.0046 (15)0.0024 (14)0.0018 (12)
C140.048 (2)0.0402 (19)0.0315 (16)0.0021 (16)0.0082 (14)0.0039 (14)
C150.064 (3)0.042 (2)0.0427 (19)0.0110 (19)0.0062 (18)0.0007 (16)
C160.106 (4)0.055 (3)0.079 (4)0.026 (3)0.031 (3)0.002 (3)
C170.233 (9)0.044 (3)0.053 (3)0.012 (4)0.015 (4)0.006 (2)
C180.113 (5)0.071 (4)0.093 (4)0.009 (3)0.012 (4)0.015 (3)
C190.075 (3)0.049 (2)0.064 (3)0.018 (2)0.003 (2)0.007 (2)
Geometric parameters (Å, º) top
Sn1—C12.131 (4)C8—H8B0.9800
Sn1—C52.146 (3)C8—H8C0.9800
Sn1—C92.147 (3)C9—C101.508 (5)
Sn1—O12.209 (2)C9—H9A0.9900
Sn1—O2i2.358 (2)C9—H9B0.9900
O1—C131.278 (4)C10—C111.527 (5)
O2—C131.249 (4)C10—H10A0.9900
O2—Sn1ii2.358 (2)C10—H10B0.9900
C1—C21.532 (5)C11—C121.494 (6)
C1—H1A0.9900C11—H11A0.9900
C1—H1B0.9900C11—H11B0.9900
C2—C31.494 (6)C12—H12A0.9800
C2—H2A0.9900C12—H12B0.9800
C2—H2B0.9900C12—H12C0.9800
C3—C41.511 (7)C13—C141.513 (4)
C3—H3A0.9900C14—C151.532 (5)
C3—H3B0.9900C14—H14A0.9900
C4—H4A0.9800C14—H14B0.9900
C4—H4B0.9800C15—C191.527 (6)
C4—H4C0.9800C15—C161.529 (6)
C5—C61.498 (6)C15—H151.0000
C5—H5A0.9900C16—C171.439 (8)
C5—H5B0.9900C16—H16A0.9900
C6—C71.514 (6)C16—H16B0.9900
C6—H6A0.9900C17—C181.439 (9)
C6—H6B0.9900C17—H17A0.9900
C7—C81.508 (7)C17—H17B0.9900
C7—H7A0.9900C18—C191.391 (7)
C7—H7B0.9900C18—H180.9500
C8—H8A0.9800C19—H190.9500
C1—Sn1—C5116.17 (16)H8B—C8—H8C109.5
C1—Sn1—C9124.25 (14)C10—C9—Sn1116.5 (2)
C1—Sn1—O192.47 (13)C10—C9—H9A108.2
C5—Sn1—O192.02 (12)Sn1—C9—H9A108.2
C1—Sn1—O2i87.54 (13)C10—C9—H9B108.2
C5—Sn1—C9118.61 (15)Sn1—C9—H9B108.2
C5—Sn1—O2i81.83 (12)H9A—C9—H9B107.3
C9—Sn1—O195.20 (11)C9—C10—C11113.3 (3)
C9—Sn1—O2i90.45 (11)C9—C10—H10A108.9
O1—Sn1—O2i173.13 (8)C11—C10—H10A108.9
C13—O1—Sn1119.1 (2)C9—C10—H10B108.9
C13—O2—Sn1ii141.31 (19)C11—C10—H10B108.9
C2—C1—Sn1114.2 (3)H10A—C10—H10B107.7
C2—C1—H1A108.7C12—C11—C10114.7 (4)
Sn1—C1—H1A108.7C12—C11—H11A108.6
C2—C1—H1B108.7C10—C11—H11A108.6
Sn1—C1—H1B108.7C12—C11—H11B108.6
H1A—C1—H1B107.6C10—C11—H11B108.6
C3—C2—C1113.1 (4)H11A—C11—H11B107.6
C3—C2—H2A109.0C11—C12—H12A109.5
C1—C2—H2A109.0C11—C12—H12B109.5
C3—C2—H2B109.0H12A—C12—H12B109.5
C1—C2—H2B109.0C11—C12—H12C109.5
H2A—C2—H2B107.8H12A—C12—H12C109.5
C2—C3—C4113.7 (4)H12B—C12—H12C109.5
C2—C3—H3A108.8O2—C13—O1122.5 (3)
C4—C3—H3A108.8O2—C13—C14120.9 (3)
C2—C3—H3B108.8O1—C13—C14116.7 (3)
C4—C3—H3B108.8C13—C14—C15112.7 (3)
H3A—C3—H3B107.7C13—C14—H14A109.0
C3—C4—H4A109.5C15—C14—H14A109.0
C3—C4—H4B109.5C13—C14—H14B109.0
H4A—C4—H4B109.5C15—C14—H14B109.0
C3—C4—H4C109.5H14A—C14—H14B107.8
H4A—C4—H4C109.5C19—C15—C16101.4 (4)
H4B—C4—H4C109.5C19—C15—C14112.2 (3)
C6—C5—Sn1118.1 (2)C16—C15—C14112.3 (3)
C6—C5—H5A107.8C19—C15—H15110.2
Sn1—C5—H5A107.8C16—C15—H15110.2
C6—C5—H5B107.8C14—C15—H15110.2
Sn1—C5—H5B107.8C17—C16—C15107.0 (4)
H5A—C5—H5B107.1C17—C16—H16A110.3
C5—C6—C7114.7 (4)C15—C16—H16A110.3
C5—C6—H6A108.6C17—C16—H16B110.3
C7—C6—H6A108.6C15—C16—H16B110.3
C5—C6—H6B108.6H16A—C16—H16B108.6
C7—C6—H6B108.6C18—C17—C16110.7 (4)
H6A—C6—H6B107.6C18—C17—H17A109.5
C8—C7—C6109.3 (4)C16—C17—H17A109.5
C8—C7—H7A109.8C18—C17—H17B109.5
C6—C7—H7A109.8C16—C17—H17B109.5
C8—C7—H7B109.8H17A—C17—H17B108.1
C6—C7—H7B109.8C19—C18—C17107.4 (5)
H7A—C7—H7B108.3C19—C18—H18126.3
C7—C8—H8A109.5C17—C18—H18126.3
C7—C8—H8B109.5C18—C19—C15111.2 (4)
H8A—C8—H8B109.5C18—C19—H19124.4
C7—C8—H8C109.5C15—C19—H19124.4
H8A—C8—H8C109.5
C1—Sn1—O1—C1365.4 (2)O2i—Sn1—C9—C1051.5 (3)
C5—Sn1—O1—C13178.3 (3)Sn1—C9—C10—C11176.9 (3)
C9—Sn1—O1—C1359.3 (2)C9—C10—C11—C12176.3 (4)
C5—Sn1—C1—C26.0 (3)Sn1ii—O2—C13—O1175.0 (2)
C9—Sn1—C1—C2174.5 (2)Sn1ii—O2—C13—C146.3 (5)
O1—Sn1—C1—C287.5 (3)Sn1—O1—C13—O20.7 (4)
O2i—Sn1—C1—C285.6 (3)Sn1—O1—C13—C14179.5 (2)
Sn1—C1—C2—C3175.7 (3)O2—C13—C14—C15142.1 (3)
C1—C2—C3—C4179.0 (4)O1—C13—C14—C1539.1 (4)
C1—Sn1—C5—C6110.8 (3)C13—C14—C15—C1963.2 (4)
C9—Sn1—C5—C680.0 (3)C13—C14—C15—C16176.7 (4)
O1—Sn1—C5—C617.0 (3)C19—C15—C16—C1713.4 (5)
O2i—Sn1—C5—C6166.0 (3)C14—C15—C16—C17106.5 (5)
Sn1—C5—C6—C767.3 (4)C15—C16—C17—C188.7 (6)
C5—C6—C7—C8177.7 (4)C16—C17—C18—C190.6 (7)
C1—Sn1—C9—C10138.8 (3)C17—C18—C19—C159.9 (6)
C5—Sn1—C9—C1029.4 (3)C16—C15—C19—C1814.5 (5)
O1—Sn1—C9—C10124.6 (3)C14—C15—C19—C18105.5 (4)
Symmetry codes: (i) x+3/2, y+3/2, z1/2; (ii) x+3/2, y+3/2, z+1/2.
 

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