metal-organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015194/tk2035sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015194/tk2035Isup2.hkl |
CCDC reference: 610913
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.
Crystal data top
[Sn(C4H9)3(C7H9O2)] | Dx = 1.298 Mg m−3 |
Mr = 415.17 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I4 | Cell parameters from 8643 reflections |
Hall symbol: I -4 | θ = 3.1–27.5° |
a = 20.559 (6) Å | µ = 1.21 mm−1 |
c = 10.053 (7) Å | T = 173 K |
V = 4249 (3) Å3 | Block, colorless |
Z = 8 | 0.20 × 0.10 × 0.09 mm |
F(000) = 1728 |
Data collection top
Nonius KappaCCD diffractometer | 4776 independent reflections |
Radiation source: fine-focus sealed tube | 4277 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω and φ scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −26→26 |
Tmin = 0.794, Tmax = 0.899 | k = −26→26 |
8643 measured reflections | l = −13→11 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-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 reflections | Δρmax = 0.41 e Å−3 |
202 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2195 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.729934 (11) | 0.780975 (11) | 0.408215 (19) | 0.03244 (7) | |
O1 | 0.67822 (11) | 0.83328 (11) | 0.56837 (19) | 0.0378 (5) | |
O2 | 0.72512 (12) | 0.77096 (11) | 0.72034 (19) | 0.0407 (5) | |
C1 | 0.6802 (2) | 0.69231 (18) | 0.4496 (4) | 0.0454 (9) | |
H1A | 0.7088 | 0.6555 | 0.4249 | 0.054* | |
H1B | 0.6722 | 0.6896 | 0.5466 | 0.054* | |
C2 | 0.61525 (19) | 0.6849 (2) | 0.3767 (4) | 0.0516 (10) | |
H2A | 0.5877 | 0.7233 | 0.3960 | 0.062* | |
H2B | 0.6235 | 0.6841 | 0.2797 | 0.062* | |
C3 | 0.5791 (2) | 0.6247 (2) | 0.4151 (5) | 0.0632 (11) | |
H3A | 0.5717 | 0.6253 | 0.5124 | 0.076* | |
H3B | 0.6064 | 0.5864 | 0.3943 | 0.076* | |
C4 | 0.5143 (2) | 0.6173 (3) | 0.3456 (5) | 0.0867 (17) | |
H4A | 0.4949 | 0.5754 | 0.3697 | 0.104* | |
H4B | 0.5208 | 0.6192 | 0.2491 | 0.104* | |
H4C | 0.4852 | 0.6527 | 0.3730 | 0.104* | |
C5 | 0.6876 (2) | 0.84172 (19) | 0.2577 (3) | 0.0487 (9) | |
H5A | 0.7218 | 0.8516 | 0.1914 | 0.058* | |
H5B | 0.6536 | 0.8160 | 0.2116 | 0.058* | |
C6 | 0.6577 (2) | 0.90486 (19) | 0.3001 (4) | 0.0539 (10) | |
H6A | 0.6251 | 0.8959 | 0.3703 | 0.065* | |
H6B | 0.6343 | 0.9238 | 0.2232 | 0.065* | |
C7 | 0.7055 (2) | 0.9547 (2) | 0.3521 (4) | 0.0640 (12) | |
H7A | 0.7301 | 0.9363 | 0.4279 | 0.077* | |
H7B | 0.7369 | 0.9664 | 0.2813 | 0.077* | |
C8 | 0.6690 (3) | 1.0146 (3) | 0.3962 (7) | 0.108 (2) | |
H8A | 0.6996 | 1.0459 | 0.4348 | 0.130* | |
H8B | 0.6365 | 1.0024 | 0.4630 | 0.130* | |
H8C | 0.6472 | 1.0343 | 0.3194 | 0.130* | |
C9 | 0.82564 (16) | 0.80398 (18) | 0.4795 (3) | 0.0381 (8) | |
H9A | 0.8211 | 0.8323 | 0.5586 | 0.046* | |
H9B | 0.8466 | 0.7631 | 0.5090 | 0.046* | |
C10 | 0.87062 (17) | 0.8372 (2) | 0.3824 (4) | 0.0485 (10) | |
H10A | 0.8515 | 0.8796 | 0.3567 | 0.058* | |
H10B | 0.8740 | 0.8103 | 0.3010 | 0.058* | |
C11 | 0.93879 (19) | 0.8486 (2) | 0.4379 (5) | 0.0595 (12) | |
H11A | 0.9350 | 0.8728 | 0.5226 | 0.071* | |
H11B | 0.9587 | 0.8059 | 0.4583 | 0.071* | |
C12 | 0.9833 (3) | 0.8851 (3) | 0.3474 (6) | 0.0891 (18) | |
H12A | 1.0264 | 0.8887 | 0.3887 | 0.107* | |
H12B | 0.9657 | 0.9287 | 0.3316 | 0.107* | |
H12C | 0.9871 | 0.8619 | 0.2626 | 0.107* | |
C13 | 0.68787 (16) | 0.81645 (16) | 0.6891 (3) | 0.0337 (7) | |
C14 | 0.65064 (18) | 0.85365 (16) | 0.7943 (3) | 0.0400 (8) | |
H14A | 0.6725 | 0.8478 | 0.8813 | 0.048* | |
H14B | 0.6063 | 0.8353 | 0.8016 | 0.048* | |
C15 | 0.6458 (2) | 0.92648 (18) | 0.7637 (4) | 0.0498 (9) | |
H15 | 0.6229 | 0.9334 | 0.6770 | 0.060* | |
C16 | 0.6115 (3) | 0.9642 (3) | 0.8745 (5) | 0.0798 (17) | |
H16A | 0.5786 | 0.9941 | 0.8364 | 0.096* | |
H16B | 0.5893 | 0.9338 | 0.9360 | 0.096* | |
C17 | 0.6608 (4) | 1.0005 (3) | 0.9441 (5) | 0.110 (3) | |
H17A | 0.6471 | 1.0465 | 0.9517 | 0.132* | |
H17B | 0.6659 | 0.9828 | 1.0351 | 0.132* | |
C18 | 0.7220 (3) | 0.9969 (3) | 0.8750 (6) | 0.0920 (17) | |
H18 | 0.7617 | 1.0166 | 0.9019 | 0.110* | |
C19 | 0.7123 (2) | 0.9594 (2) | 0.7615 (5) | 0.0627 (12) | |
H19 | 0.7432 | 0.9549 | 0.6917 | 0.075* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03661 (14) | 0.03573 (14) | 0.02497 (9) | 0.00165 (11) | −0.00274 (10) | 0.00074 (10) |
O1 | 0.0439 (13) | 0.0432 (13) | 0.0264 (11) | 0.0080 (10) | 0.0043 (9) | 0.0016 (9) |
O2 | 0.0509 (16) | 0.0404 (15) | 0.0310 (9) | 0.0099 (13) | 0.0018 (12) | 0.0038 (10) |
C1 | 0.055 (2) | 0.038 (2) | 0.044 (2) | −0.0097 (17) | −0.0046 (17) | 0.0037 (15) |
C2 | 0.051 (2) | 0.065 (3) | 0.039 (2) | −0.012 (2) | 0.0041 (16) | −0.0017 (17) |
C3 | 0.070 (3) | 0.067 (3) | 0.053 (2) | −0.019 (2) | 0.016 (2) | −0.010 (2) |
C4 | 0.061 (3) | 0.131 (5) | 0.068 (3) | −0.033 (3) | 0.003 (3) | −0.007 (3) |
C5 | 0.060 (3) | 0.050 (2) | 0.0366 (18) | 0.009 (2) | −0.0134 (17) | 0.0037 (16) |
C6 | 0.057 (3) | 0.057 (3) | 0.048 (2) | 0.003 (2) | −0.0066 (18) | 0.0098 (19) |
C7 | 0.087 (3) | 0.044 (2) | 0.061 (3) | −0.012 (2) | −0.022 (2) | 0.013 (2) |
C8 | 0.147 (6) | 0.072 (4) | 0.105 (5) | 0.010 (4) | −0.045 (5) | 0.009 (4) |
C9 | 0.0353 (19) | 0.048 (2) | 0.0307 (16) | 0.0016 (16) | −0.0025 (14) | −0.0039 (15) |
C10 | 0.040 (2) | 0.060 (2) | 0.046 (2) | −0.0054 (18) | −0.0055 (16) | 0.0074 (18) |
C11 | 0.043 (2) | 0.068 (3) | 0.068 (3) | −0.009 (2) | −0.004 (2) | −0.005 (2) |
C12 | 0.061 (3) | 0.094 (4) | 0.112 (4) | −0.026 (3) | −0.006 (3) | 0.031 (3) |
C13 | 0.0393 (18) | 0.0328 (17) | 0.0290 (15) | −0.0046 (15) | 0.0024 (14) | 0.0018 (12) |
C14 | 0.048 (2) | 0.0402 (19) | 0.0315 (16) | 0.0021 (16) | 0.0082 (14) | −0.0039 (14) |
C15 | 0.064 (3) | 0.042 (2) | 0.0427 (19) | 0.0110 (19) | 0.0062 (18) | −0.0007 (16) |
C16 | 0.106 (4) | 0.055 (3) | 0.079 (4) | 0.026 (3) | 0.031 (3) | 0.002 (3) |
C17 | 0.233 (9) | 0.044 (3) | 0.053 (3) | 0.012 (4) | 0.015 (4) | −0.006 (2) |
C18 | 0.113 (5) | 0.071 (4) | 0.093 (4) | −0.009 (3) | −0.012 (4) | −0.015 (3) |
C19 | 0.075 (3) | 0.049 (2) | 0.064 (3) | −0.018 (2) | 0.003 (2) | −0.007 (2) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.131 (4) | C8—H8B | 0.9800 |
Sn1—C5 | 2.146 (3) | C8—H8C | 0.9800 |
Sn1—C9 | 2.147 (3) | C9—C10 | 1.508 (5) |
Sn1—O1 | 2.209 (2) | C9—H9A | 0.9900 |
Sn1—O2i | 2.358 (2) | C9—H9B | 0.9900 |
O1—C13 | 1.278 (4) | C10—C11 | 1.527 (5) |
O2—C13 | 1.249 (4) | C10—H10A | 0.9900 |
O2—Sn1ii | 2.358 (2) | C10—H10B | 0.9900 |
C1—C2 | 1.532 (5) | C11—C12 | 1.494 (6) |
C1—H1A | 0.9900 | C11—H11A | 0.9900 |
C1—H1B | 0.9900 | C11—H11B | 0.9900 |
C2—C3 | 1.494 (6) | C12—H12A | 0.9800 |
C2—H2A | 0.9900 | C12—H12B | 0.9800 |
C2—H2B | 0.9900 | C12—H12C | 0.9800 |
C3—C4 | 1.511 (7) | C13—C14 | 1.513 (4) |
C3—H3A | 0.9900 | C14—C15 | 1.532 (5) |
C3—H3B | 0.9900 | C14—H14A | 0.9900 |
C4—H4A | 0.9800 | C14—H14B | 0.9900 |
C4—H4B | 0.9800 | C15—C19 | 1.527 (6) |
C4—H4C | 0.9800 | C15—C16 | 1.529 (6) |
C5—C6 | 1.498 (6) | C15—H15 | 1.0000 |
C5—H5A | 0.9900 | C16—C17 | 1.439 (8) |
C5—H5B | 0.9900 | C16—H16A | 0.9900 |
C6—C7 | 1.514 (6) | C16—H16B | 0.9900 |
C6—H6A | 0.9900 | C17—C18 | 1.439 (9) |
C6—H6B | 0.9900 | C17—H17A | 0.9900 |
C7—C8 | 1.508 (7) | C17—H17B | 0.9900 |
C7—H7A | 0.9900 | C18—C19 | 1.391 (7) |
C7—H7B | 0.9900 | C18—H18 | 0.9500 |
C8—H8A | 0.9800 | C19—H19 | 0.9500 |
C1—Sn1—C5 | 116.17 (16) | H8B—C8—H8C | 109.5 |
C1—Sn1—C9 | 124.25 (14) | C10—C9—Sn1 | 116.5 (2) |
C1—Sn1—O1 | 92.47 (13) | C10—C9—H9A | 108.2 |
C5—Sn1—O1 | 92.02 (12) | Sn1—C9—H9A | 108.2 |
C1—Sn1—O2i | 87.54 (13) | C10—C9—H9B | 108.2 |
C5—Sn1—C9 | 118.61 (15) | Sn1—C9—H9B | 108.2 |
C5—Sn1—O2i | 81.83 (12) | H9A—C9—H9B | 107.3 |
C9—Sn1—O1 | 95.20 (11) | C9—C10—C11 | 113.3 (3) |
C9—Sn1—O2i | 90.45 (11) | C9—C10—H10A | 108.9 |
O1—Sn1—O2i | 173.13 (8) | C11—C10—H10A | 108.9 |
C13—O1—Sn1 | 119.1 (2) | C9—C10—H10B | 108.9 |
C13—O2—Sn1ii | 141.31 (19) | C11—C10—H10B | 108.9 |
C2—C1—Sn1 | 114.2 (3) | H10A—C10—H10B | 107.7 |
C2—C1—H1A | 108.7 | C12—C11—C10 | 114.7 (4) |
Sn1—C1—H1A | 108.7 | C12—C11—H11A | 108.6 |
C2—C1—H1B | 108.7 | C10—C11—H11A | 108.6 |
Sn1—C1—H1B | 108.7 | C12—C11—H11B | 108.6 |
H1A—C1—H1B | 107.6 | C10—C11—H11B | 108.6 |
C3—C2—C1 | 113.1 (4) | H11A—C11—H11B | 107.6 |
C3—C2—H2A | 109.0 | C11—C12—H12A | 109.5 |
C1—C2—H2A | 109.0 | C11—C12—H12B | 109.5 |
C3—C2—H2B | 109.0 | H12A—C12—H12B | 109.5 |
C1—C2—H2B | 109.0 | C11—C12—H12C | 109.5 |
H2A—C2—H2B | 107.8 | H12A—C12—H12C | 109.5 |
C2—C3—C4 | 113.7 (4) | H12B—C12—H12C | 109.5 |
C2—C3—H3A | 108.8 | O2—C13—O1 | 122.5 (3) |
C4—C3—H3A | 108.8 | O2—C13—C14 | 120.9 (3) |
C2—C3—H3B | 108.8 | O1—C13—C14 | 116.7 (3) |
C4—C3—H3B | 108.8 | C13—C14—C15 | 112.7 (3) |
H3A—C3—H3B | 107.7 | C13—C14—H14A | 109.0 |
C3—C4—H4A | 109.5 | C15—C14—H14A | 109.0 |
C3—C4—H4B | 109.5 | C13—C14—H14B | 109.0 |
H4A—C4—H4B | 109.5 | C15—C14—H14B | 109.0 |
C3—C4—H4C | 109.5 | H14A—C14—H14B | 107.8 |
H4A—C4—H4C | 109.5 | C19—C15—C16 | 101.4 (4) |
H4B—C4—H4C | 109.5 | C19—C15—C14 | 112.2 (3) |
C6—C5—Sn1 | 118.1 (2) | C16—C15—C14 | 112.3 (3) |
C6—C5—H5A | 107.8 | C19—C15—H15 | 110.2 |
Sn1—C5—H5A | 107.8 | C16—C15—H15 | 110.2 |
C6—C5—H5B | 107.8 | C14—C15—H15 | 110.2 |
Sn1—C5—H5B | 107.8 | C17—C16—C15 | 107.0 (4) |
H5A—C5—H5B | 107.1 | C17—C16—H16A | 110.3 |
C5—C6—C7 | 114.7 (4) | C15—C16—H16A | 110.3 |
C5—C6—H6A | 108.6 | C17—C16—H16B | 110.3 |
C7—C6—H6A | 108.6 | C15—C16—H16B | 110.3 |
C5—C6—H6B | 108.6 | H16A—C16—H16B | 108.6 |
C7—C6—H6B | 108.6 | C18—C17—C16 | 110.7 (4) |
H6A—C6—H6B | 107.6 | C18—C17—H17A | 109.5 |
C8—C7—C6 | 109.3 (4) | C16—C17—H17A | 109.5 |
C8—C7—H7A | 109.8 | C18—C17—H17B | 109.5 |
C6—C7—H7A | 109.8 | C16—C17—H17B | 109.5 |
C8—C7—H7B | 109.8 | H17A—C17—H17B | 108.1 |
C6—C7—H7B | 109.8 | C19—C18—C17 | 107.4 (5) |
H7A—C7—H7B | 108.3 | C19—C18—H18 | 126.3 |
C7—C8—H8A | 109.5 | C17—C18—H18 | 126.3 |
C7—C8—H8B | 109.5 | C18—C19—C15 | 111.2 (4) |
H8A—C8—H8B | 109.5 | C18—C19—H19 | 124.4 |
C7—C8—H8C | 109.5 | C15—C19—H19 | 124.4 |
H8A—C8—H8C | 109.5 | ||
C1—Sn1—O1—C13 | 65.4 (2) | O2i—Sn1—C9—C10 | 51.5 (3) |
C5—Sn1—O1—C13 | −178.3 (3) | Sn1—C9—C10—C11 | −176.9 (3) |
C9—Sn1—O1—C13 | −59.3 (2) | C9—C10—C11—C12 | −176.3 (4) |
C5—Sn1—C1—C2 | −6.0 (3) | Sn1ii—O2—C13—O1 | 175.0 (2) |
C9—Sn1—C1—C2 | −174.5 (2) | Sn1ii—O2—C13—C14 | −6.3 (5) |
O1—Sn1—C1—C2 | 87.5 (3) | Sn1—O1—C13—O2 | −0.7 (4) |
O2i—Sn1—C1—C2 | −85.6 (3) | Sn1—O1—C13—C14 | −179.5 (2) |
Sn1—C1—C2—C3 | −175.7 (3) | O2—C13—C14—C15 | 142.1 (3) |
C1—C2—C3—C4 | 179.0 (4) | O1—C13—C14—C15 | −39.1 (4) |
C1—Sn1—C5—C6 | 110.8 (3) | C13—C14—C15—C19 | −63.2 (4) |
C9—Sn1—C5—C6 | −80.0 (3) | C13—C14—C15—C16 | −176.7 (4) |
O1—Sn1—C5—C6 | 17.0 (3) | C19—C15—C16—C17 | −13.4 (5) |
O2i—Sn1—C5—C6 | −166.0 (3) | C14—C15—C16—C17 | 106.5 (5) |
Sn1—C5—C6—C7 | 67.3 (4) | C15—C16—C17—C18 | 8.7 (6) |
C5—C6—C7—C8 | −177.7 (4) | C16—C17—C18—C19 | 0.6 (7) |
C1—Sn1—C9—C10 | 138.8 (3) | C17—C18—C19—C15 | −9.9 (6) |
C5—Sn1—C9—C10 | −29.4 (3) | C16—C15—C19—C18 | 14.5 (5) |
O1—Sn1—C9—C10 | −124.6 (3) | C14—C15—C19—C18 | −105.5 (4) |
Symmetry codes: (i) −x+3/2, −y+3/2, z−1/2; (ii) −x+3/2, −y+3/2, z+1/2. |