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The crystal structure of the title compound, tetra-μ2-(cyclopent-2-en­yl)acetato-1:2κ2O:O′;1:3κ2O:O′;2:4κ2O:O′;3:4κ2O:O′-octa­methyl-1κ2C,2κ2C,3κ2C,4κ2C-di-μ3-oxo-1:2:3κ3O;2:3:4κ3O-tetra­tin(IV), [Sn4(CH3)8(C7H9O2)4O2], is composed of discrete centrosymmetric dimers lying about inversion centres. The cyclo­pentenylacetate ligand shows different modes of coordination with Sn, as a result of which the central Sn2O2 core is fused with two four-membered (Sn2O2) and two six-membered (Sn2O3C) rings. The endocyclic Sn atoms are six-coordinate in a skew-trapezoidal bipyramidal environment. The exocyclic Sn atoms are five-coordinate and show distorted trigonal–bipyramidal geometry. The Sn—C distances lie in a very narrow range [2.095 (4)–2.113 (4) Å], while the Sn—O distances range between 2.030 (3) and 2.280 (3) Å for strong bonds and a value of 2.654 (3) Å for the relatively weak Sn—O bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014966/lh2056sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014966/lh2056Isup2.hkl
Contains datablock I

CCDC reference: 608460

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.036
  • wR factor = 0.084
  • Data-to-parameter ratio = 21.0

checkCIF/PLATON results

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Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C18 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C18'
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C22 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C22' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C12 - C13 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 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 11 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: COLLECT (Nonius, 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 (Sheldrick, 1997).

tetra-µ2-(cyclopent-2-enyl)acetato- 1:2κ2O:O';1:3κ2O:O';2:4κ2O:O';3:4κ2O:O'-octamethyl- 1κ2C,2κ2C,3κ2C,4κ2C-di-µ3-oxo-1:2:3κ3O;2:3:4κ3O-tetratin top
Crystal data top
[Sn4(CH3)8(C7H9O2)4O2]Z = 1
Mr = 1127.60F(000) = 556
Triclinic, P1Dx = 1.714 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.572 (2) ÅCell parameters from 9218 reflections
b = 11.154 (3) Åθ = 3.5–27.5°
c = 13.387 (4) ŵ = 2.31 mm1
α = 84.584 (9)°T = 173 K
β = 76.014 (9)°Prism, colourless
γ = 89.404 (15)°0.10 × 0.09 × 0.08 mm
V = 1092.1 (5) Å3
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
4974 independent reflections
Radiation source: fine-focus sealed tube3581 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω and φ scansθmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 99
Tmin = 0.802, Tmax = 0.837k = 1414
9216 measured reflectionsl = 1717
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) = 0.084H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0404P)2]
where P = (Fo2 + 2Fc2)/3
4974 reflections(Δ/σ)max = 0.003
237 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.79 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.01104 (3)0.44836 (2)0.61638 (2)0.02754 (10)
Sn20.00626 (3)0.21358 (2)0.44736 (2)0.02822 (10)
C10.2889 (5)0.4199 (4)0.6087 (4)0.0487 (12)
H1A0.35650.49590.58530.073*
H1B0.33530.36020.55990.073*
H1C0.30420.39030.67730.073*
C30.2578 (5)0.4013 (4)0.6989 (3)0.0424 (11)
H3A0.32580.47450.71710.064*
H3B0.25500.35010.76210.064*
H3C0.31730.35750.65570.064*
C50.2830 (5)0.1724 (4)0.4014 (4)0.0445 (12)
H5A0.35470.24720.38020.067*
H5B0.30280.12280.34320.067*
H5C0.32090.12810.45930.067*
C70.2727 (5)0.1707 (4)0.4812 (4)0.0443 (12)
H7A0.34340.24480.48820.066*
H7B0.30610.11830.54600.066*
H7C0.29870.12890.42500.066*
O10.0050 (3)0.3935 (2)0.46921 (19)0.0291 (6)
O20.0210 (5)0.4483 (3)0.2460 (2)0.0595 (9)
O30.0058 (5)0.2544 (3)0.2821 (2)0.0595 (9)
C90.0161 (5)0.3426 (4)0.2229 (3)0.0313 (9)
C100.0391 (5)0.3232 (4)0.1173 (3)0.0367 (10)
H10A0.04960.23570.11230.044*
H10B0.07090.35380.06490.044*
C110.2043 (5)0.3848 (4)0.0926 (3)0.0411 (11)
H110.19250.47350.09570.049*
C120.3831 (6)0.3390 (6)0.1665 (4)0.0620 (15)
H12A0.36240.26290.20610.074*
H12B0.43000.39910.21610.074*
C130.5127 (7)0.3194 (6)0.1072 (4)0.0716 (17)
H13A0.60840.38130.11780.086*
H13B0.57110.23910.12850.086*
C140.4113 (7)0.3275 (6)0.0025 (4)0.0740 (18)
H140.46170.31090.05820.089*
C150.2345 (6)0.3621 (5)0.0124 (3)0.0535 (13)
H150.14390.37070.07570.064*
O40.0134 (4)0.2107 (3)0.6137 (2)0.0362 (7)
O50.0040 (4)0.0159 (3)0.6127 (3)0.0586 (9)
C160.0052 (5)0.1032 (4)0.6598 (3)0.0345 (10)
C170.0089 (7)0.0896 (6)0.7710 (4)0.0719 (18)
H17A0.09580.13330.81020.086*0.706 (11)
H17B0.00850.00320.79640.086*0.706 (11)
C180.1690 (9)0.1313 (7)0.7934 (5)0.047 (2)0.706 (11)
H180.18580.21930.77040.056*0.706 (11)
C190.3456 (7)0.0633 (7)0.7441 (4)0.085 (2)
H19A0.31410.01730.72790.102*0.706 (11)
H19B0.41260.10910.67930.102*0.706 (11)
C200.4567 (8)0.0521 (7)0.8190 (6)0.100 (2)
H20A0.51570.02750.81920.120*
H20B0.55230.11570.80270.120*
C210.3329 (9)0.0652 (6)0.9182 (5)0.085 (2)
H210.36100.04480.98310.102*0.706 (11)
C220.170 (3)0.1107 (14)0.9062 (13)0.082 (5)0.706 (11)
H220.07070.12710.96160.098*0.706 (11)
H17C0.01240.17100.79490.086*0.294 (11)
H17D0.10020.04060.80700.086*0.294 (11)
C18'0.150 (2)0.0425 (18)0.8111 (12)0.047 (2)0.294 (11)
H18'0.13140.04660.81490.056*0.294 (11)
H19C0.37820.00200.69410.102*0.294 (11)
H19D0.35970.14440.70580.102*0.294 (11)
H21'0.37020.07530.97980.102*0.294 (11)
C22'0.185 (7)0.062 (4)0.913 (4)0.082 (5)0.294 (11)
H22'0.08780.07080.97180.098*0.294 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03292 (17)0.02655 (17)0.02504 (16)0.00020 (12)0.01119 (12)0.00104 (12)
Sn20.03069 (16)0.02551 (17)0.02923 (17)0.00312 (11)0.00784 (12)0.00516 (12)
C10.037 (2)0.045 (3)0.068 (4)0.001 (2)0.024 (2)0.004 (3)
C30.041 (2)0.041 (3)0.039 (3)0.000 (2)0.002 (2)0.005 (2)
C50.034 (2)0.040 (3)0.052 (3)0.0042 (19)0.005 (2)0.004 (2)
C70.033 (2)0.036 (3)0.069 (3)0.0009 (19)0.018 (2)0.014 (2)
O10.0400 (15)0.0236 (15)0.0254 (15)0.0013 (12)0.0100 (12)0.0059 (12)
O20.112 (3)0.042 (2)0.0336 (19)0.0091 (19)0.0341 (19)0.0042 (16)
O30.108 (3)0.044 (2)0.0307 (19)0.0124 (19)0.0258 (19)0.0055 (16)
C90.026 (2)0.047 (3)0.020 (2)0.0023 (18)0.0037 (16)0.003 (2)
C100.039 (2)0.043 (3)0.030 (2)0.0016 (19)0.0099 (19)0.011 (2)
C110.045 (3)0.055 (3)0.024 (2)0.000 (2)0.0094 (19)0.007 (2)
C120.041 (3)0.103 (5)0.040 (3)0.000 (3)0.003 (2)0.014 (3)
C130.060 (3)0.102 (5)0.055 (4)0.018 (3)0.017 (3)0.005 (3)
C140.073 (4)0.115 (5)0.039 (3)0.026 (3)0.021 (3)0.008 (3)
C150.050 (3)0.087 (4)0.027 (2)0.006 (3)0.016 (2)0.005 (3)
O40.0435 (16)0.0355 (18)0.0312 (16)0.0019 (13)0.0127 (13)0.0028 (14)
O50.068 (2)0.032 (2)0.075 (3)0.0029 (16)0.0166 (19)0.0021 (18)
C160.028 (2)0.037 (3)0.035 (2)0.0066 (19)0.0020 (18)0.004 (2)
C170.057 (3)0.123 (6)0.030 (3)0.027 (3)0.010 (2)0.014 (3)
C180.063 (4)0.047 (4)0.035 (4)0.004 (4)0.021 (3)0.001 (3)
C190.049 (3)0.157 (7)0.057 (4)0.023 (4)0.019 (3)0.033 (4)
C200.068 (4)0.141 (7)0.103 (6)0.021 (4)0.036 (4)0.033 (5)
C210.095 (5)0.113 (6)0.064 (4)0.026 (4)0.052 (4)0.014 (4)
C220.094 (6)0.124 (15)0.039 (4)0.054 (9)0.034 (4)0.026 (8)
C17'0.057 (3)0.123 (6)0.030 (3)0.027 (3)0.010 (2)0.014 (3)
C18'0.063 (4)0.047 (4)0.035 (4)0.004 (4)0.021 (3)0.001 (3)
C19'0.049 (3)0.157 (7)0.057 (4)0.023 (4)0.019 (3)0.033 (4)
C20'0.068 (4)0.141 (7)0.103 (6)0.021 (4)0.036 (4)0.033 (5)
C21'0.095 (5)0.113 (6)0.064 (4)0.026 (4)0.052 (4)0.014 (4)
C22'0.094 (6)0.124 (15)0.039 (4)0.054 (9)0.034 (4)0.026 (8)
Geometric parameters (Å, º) top
Sn1—O1i2.030 (3)C11—C121.531 (6)
Sn1—C12.104 (4)C11—H111.0000
Sn1—C32.113 (4)C12—C131.433 (6)
Sn1—O12.128 (3)C12—H12A0.9900
Sn1—O2i2.280 (3)C12—H12B0.9900
Sn1—O42.654 (3)C13—C141.478 (7)
Sn2—O12.054 (3)C13—H13A0.9900
Sn2—C52.095 (4)C13—H13B0.9900
Sn2—C72.101 (4)C14—C151.369 (6)
Sn2—O32.218 (3)C14—H140.9500
Sn2—O42.238 (3)C15—H150.9500
C1—H1A0.9800O4—C161.291 (5)
C1—H1B0.9800O5—C161.220 (5)
C1—H1C0.9800C16—C171.489 (6)
C3—H3A0.9800C17—C181.411 (8)
C3—H3B0.9800C17—H17A0.9900
C3—H3C0.9800C17—H17B0.9900
C5—H5A0.9800C18—C221.508 (17)
C5—H5B0.9800C18—C191.564 (8)
C5—H5C0.9800C18—H181.0000
C7—H7A0.9800C19—C201.453 (8)
C7—H7B0.9800C19—H19A0.9900
C7—H7C0.9800C19—H19B0.9900
O1—Sn1i2.030 (3)C20—C211.447 (8)
O2—C91.245 (5)C20—H20A0.9900
O2—Sn1i2.280 (3)C20—H20B0.9900
O3—C91.239 (5)C21—C221.368 (16)
C9—C101.502 (6)C21—H210.9500
C10—C111.511 (6)C22—H220.9500
C10—H10A0.9900C18'—C22'1.49 (5)
C10—H10B0.9900C18'—H18'1.0000
C11—C151.522 (6)C22'—H22'0.9500
O1i—Sn1—C1106.63 (15)C10—C11—C15114.1 (4)
O1i—Sn1—C3106.36 (14)C10—C11—C12112.9 (4)
C1—Sn1—C3145.21 (19)C15—C11—C12102.3 (3)
O1i—Sn1—O176.74 (11)C10—C11—H11109.1
C1—Sn1—O198.32 (15)C15—C11—H11109.1
C3—Sn1—O199.69 (14)C12—C11—H11109.1
O1i—Sn1—O2i89.75 (11)C13—C12—C11108.8 (4)
C1—Sn1—O2i84.06 (17)C13—C12—H12A109.9
C3—Sn1—O2i85.31 (15)C11—C12—H12A109.9
O1—Sn1—O2i166.42 (11)C13—C12—H12B109.9
O1i—Sn1—O4143.97 (10)C11—C12—H12B109.9
C1—Sn1—O481.41 (14)H12A—C12—H12B108.3
C3—Sn1—O478.49 (13)C12—C13—C14106.8 (4)
O1—Sn1—O467.29 (9)C12—C13—H13A110.4
O2i—Sn1—O4126.25 (10)C14—C13—H13A110.4
O1—Sn2—C5104.20 (14)C12—C13—H13B110.4
O1—Sn2—C7102.44 (14)C14—C13—H13B110.4
C5—Sn2—C7153.34 (17)H13A—C13—H13B108.6
O1—Sn2—O391.70 (11)C15—C14—C13110.5 (4)
C5—Sn2—O388.71 (16)C15—C14—H14124.8
C7—Sn2—O389.67 (17)C13—C14—H14124.8
O1—Sn2—O477.33 (10)C14—C15—C11110.1 (4)
C5—Sn2—O492.66 (15)C14—C15—H15124.9
C7—Sn2—O493.96 (15)C11—C15—H15124.9
O3—Sn2—O4168.95 (12)C16—O4—Sn2113.0 (3)
Sn1—C1—H1A109.5C16—O4—Sn1151.5 (3)
Sn1—C1—H1B109.5Sn2—O4—Sn195.26 (10)
H1A—C1—H1B109.5O5—C16—O4120.4 (4)
Sn1—C1—H1C109.5O5—C16—C17121.5 (4)
H1A—C1—H1C109.5O4—C16—C17118.1 (4)
H1B—C1—H1C109.5C18—C17—C16115.5 (5)
Sn1—C3—H3A109.5C18—C17—H17A108.4
Sn1—C3—H3B109.5C16—C17—H17A108.4
H3A—C3—H3B109.5C18—C17—H17B108.4
Sn1—C3—H3C109.5C16—C17—H17B108.4
H3A—C3—H3C109.5H17A—C17—H17B107.5
H3B—C3—H3C109.5C17—C18—C22113.7 (10)
Sn2—C5—H5A109.5C17—C18—C19114.7 (6)
Sn2—C5—H5B109.5C22—C18—C19100.3 (7)
H5A—C5—H5B109.5C17—C18—H18109.3
Sn2—C5—H5C109.5C22—C18—H18109.3
H5A—C5—H5C109.5C19—C18—H18109.3
H5B—C5—H5C109.5C20—C19—C18107.3 (5)
Sn2—C7—H7A109.5C20—C19—H19A110.3
Sn2—C7—H7B109.5C18—C19—H19A110.3
H7A—C7—H7B109.5C20—C19—H19B110.3
Sn2—C7—H7C109.5C18—C19—H19B110.3
H7A—C7—H7C109.5H19A—C19—H19B108.5
H7B—C7—H7C109.5C21—C20—C19105.7 (5)
Sn1i—O1—Sn2136.57 (13)C21—C20—H20A110.6
Sn1i—O1—Sn1103.26 (11)C19—C20—H20A110.6
Sn2—O1—Sn1120.12 (12)C21—C20—H20B110.6
C9—O2—Sn1i139.4 (3)C19—C20—H20B110.6
C9—O3—Sn2138.3 (3)H20A—C20—H20B108.7
O3—C9—O2123.6 (4)C22—C21—C20111.0 (9)
O3—C9—C10119.3 (4)C22—C21—H21124.5
O2—C9—C10117.1 (4)C20—C21—H21124.5
C9—C10—C11113.2 (3)C21—C22—C18111.1 (12)
C9—C10—H10A108.9C21—C22—H22124.5
C11—C10—H10A108.9C18—C22—H22124.5
C9—C10—H10B108.9C22'—C18'—H18'103.8
C11—C10—H10B108.9C18'—C22'—H22'121.3
H10A—C10—H10B107.7
C5—Sn2—O1—Sn1i93.6 (2)C11—C12—C13—C1411.3 (7)
C7—Sn2—O1—Sn1i85.5 (2)C12—C13—C14—C155.9 (8)
O3—Sn2—O1—Sn1i4.5 (2)C13—C14—C15—C112.0 (7)
O4—Sn2—O1—Sn1i176.9 (2)C10—C11—C15—C14130.7 (5)
O5—Sn2—O1—Sn1i173.47 (14)C12—C11—C15—C148.4 (6)
O2—Sn2—O1—Sn1i0.98 (14)O1—Sn2—O4—C16176.0 (3)
C5—Sn2—O1—Sn189.47 (18)C5—Sn2—O4—C1680.1 (3)
C7—Sn2—O1—Sn191.39 (18)C7—Sn2—O4—C1674.1 (3)
O3—Sn2—O1—Sn1178.57 (14)O3—Sn2—O4—C16177.0 (5)
O4—Sn2—O1—Sn10.08 (11)O5—Sn2—O4—C160.2 (2)
O5—Sn2—O1—Sn13.46 (18)O1—Sn2—O4—Sn10.06 (7)
O2—Sn2—O1—Sn1177.92 (16)C5—Sn2—O4—Sn1103.91 (14)
O1i—Sn1—O1—Sn1i0.0C7—Sn2—O4—Sn1101.93 (14)
C1—Sn1—O1—Sn1i105.23 (15)O3—Sn2—O4—Sn17.0 (6)
C3—Sn1—O1—Sn1i104.67 (15)O1i—Sn1—O4—C16168.5 (5)
O2i—Sn1—O1—Sn1i6.0 (5)C1—Sn1—O4—C1684.9 (5)
O4—Sn1—O1—Sn1i177.76 (13)C3—Sn1—O4—C1666.5 (5)
O1i—Sn1—O1—Sn2177.84 (19)O1—Sn1—O4—C16172.2 (5)
C1—Sn1—O1—Sn276.94 (17)O2i—Sn1—O4—C168.9 (5)
C3—Sn1—O1—Sn273.16 (17)Sn1i—Sn1—O4—C16170.8 (5)
O2i—Sn1—O1—Sn2176.1 (4)O1i—Sn1—O4—Sn23.8 (2)
O4—Sn1—O1—Sn20.07 (10)C1—Sn1—O4—Sn2102.76 (16)
Sn1i—Sn1—O1—Sn2177.84 (19)C3—Sn1—O4—Sn2105.80 (15)
O1—Sn2—O3—C910.9 (5)O1—Sn1—O4—Sn20.06 (8)
C5—Sn2—O3—C9115.1 (5)O2i—Sn1—O4—Sn2178.84 (11)
C7—Sn2—O3—C991.5 (5)Sn1i—Sn1—O4—Sn21.46 (9)
O4—Sn2—O3—C917.8 (10)Sn2—O4—C16—O50.5 (5)
O5—Sn2—O3—C9166.2 (4)Sn1—O4—C16—O5172.1 (3)
O2—Sn2—O3—C95.7 (4)Sn2—O4—C16—C17180.0 (3)
Sn2—O3—C9—O211.3 (7)Sn1—O4—C16—C178.3 (7)
Sn2—O3—C9—C10168.4 (3)O5—C16—C17—C18116.8 (6)
Sn1i—O2—C9—O33.2 (7)O4—C16—C17—C1862.7 (7)
Sn2—O2—C9—O35.2 (3)C16—C17—C18—C22177.4 (7)
Sn1i—O2—C9—C10176.6 (3)C16—C17—C18—C1962.9 (8)
Sn2—O2—C9—C10174.6 (4)C17—C18—C19—C20142.2 (6)
O3—C9—C10—C11128.8 (4)C22—C18—C19—C2020.0 (11)
O2—C9—C10—C1151.0 (5)C18—C19—C20—C2121.4 (8)
C9—C10—C11—C15177.6 (4)C19—C20—C21—C2214.3 (12)
C9—C10—C11—C1261.4 (5)C20—C21—C22—C180.9 (16)
C10—C11—C12—C13135.1 (5)C17—C18—C22—C21134.5 (12)
C15—C11—C12—C1312.0 (6)C19—C18—C22—C2111.7 (15)
Symmetry code: (i) x, y+1, z+1.
 

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