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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
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.007 Å
- R factor = 0.028
- wR factor = 0.062
- Data-to-parameter ratio = 23.6
checkCIF/PLATON results
No syntax errors found
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.
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. |
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