Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001876/sk1351sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001876/sk1351Isup2.hkl |
Anhydrous zinc(II) octanoate was synthesized after a weakly acidic solution of zinc nitrate (pH 5.5) was added to a solution of sodium octanoate in solvent?. The precipitate, (I), was washed with distilled water and dried. Finally, compound (I) was recrystallized from ethanol at room temperature. Colourless crystals appeared as small plates with well developed (100) faces.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ATOMS (Dowty, 1995); software used to prepare material for publication: WINWORD Version 5.0.
[Zn(C8H15O2)2] | F(000) = 376 |
Mr = 351.79 | Dx = 1.301 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
a = 21.093 (2) Å | Cell parameters from 62153 reflections |
b = 4.6905 (3) Å | θ = 1.0–27.5° |
c = 9.2544 (9) Å | µ = 1.38 mm−1 |
β = 101.323 (3)° | T = 150 K |
V = 897.78 (14) Å3 | Plate, colourless |
Z = 2 | 0.30 × 0.20 × 0.02 mm |
Nonius CCD area detector diffractometer | 2984 independent reflections |
Radiation source: fine-focus sealed tube | 2231 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
CCD scans | θmax = 24.7°, θmin = 2.0° |
Absorption correction: empirical (using intensity measurements) fitted by spherical harmonic functions (SORTAV; Blessing, 1995) | h = −24→24 |
Tmin = 0.751, Tmax = 0.976 | k = −5→5 |
14913 measured reflections | l = −10→10 |
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)] = 0.058 | H-atom parameters not refined |
wR(F2) = 0.167 | Calculated w = 1/[σ2(Fo2) + (0.079P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.007 |
2984 reflections | Δρmax = 0.57 e Å−3 |
191 parameters | Δρmin = −0.66 e Å−3 |
16 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (3) |
[Zn(C8H15O2)2] | V = 897.78 (14) Å3 |
Mr = 351.79 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 21.093 (2) Å | µ = 1.38 mm−1 |
b = 4.6905 (3) Å | T = 150 K |
c = 9.2544 (9) Å | 0.30 × 0.20 × 0.02 mm |
β = 101.323 (3)° |
Nonius CCD area detector diffractometer | 2984 independent reflections |
Absorption correction: empirical (using intensity measurements) fitted by spherical harmonic functions (SORTAV; Blessing, 1995) | 2231 reflections with I > 2σ(I) |
Tmin = 0.751, Tmax = 0.976 | Rint = 0.095 |
14913 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters not refined |
wR(F2) = 0.167 | Δρmax = 0.57 e Å−3 |
S = 1.00 | Δρmin = −0.66 e Å−3 |
2984 reflections | Absolute structure: Flack (1983) |
191 parameters | Absolute structure parameter: 0.02 (3) |
16 restraints |
Experimental. The crystal to detector distance was 39.6 (1) mm. 924 frames were recorded by the oscillation method with an exposure time of 120 s per frame. |
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. |
x | y | z | Uiso*/Ueq | ||
Zn | 0.00002 (6) | 0.0581 (2) | −0.00046 (7) | 0.0243 (3) | |
O11 | −0.0219 (3) | −0.5357 (13) | −0.0340 (6) | 0.0304 (17) | |
O12 | −0.0795 (3) | −0.1493 (13) | −0.0857 (6) | 0.0271 (15) | |
C11 | −0.0714 (4) | −0.408 (2) | −0.1056 (9) | 0.026 (2) | |
C12 | −0.1212 (5) | −0.567 (2) | −0.2202 (10) | 0.029 (2) | |
H12A | −0.0983 | −0.6792 | −0.2818 | 0.034* | |
H12B | −0.1446 | −0.6988 | −0.1691 | 0.034* | |
C13 | −0.1695 (5) | −0.3768 (19) | −0.3184 (10) | 0.031 (2) | |
H13A | −0.1468 | −0.2530 | −0.3751 | 0.037* | |
H13B | −0.1913 | −0.2576 | −0.2577 | 0.037* | |
C14 | −0.2192 (5) | −0.551 (2) | −0.4226 (9) | 0.033 (2) | |
H14A | −0.2406 | −0.6799 | −0.3654 | 0.040* | |
H14B | −0.1973 | −0.6658 | −0.4849 | 0.040* | |
C15 | −0.2703 (4) | −0.367 (2) | −0.5201 (9) | 0.031 (2) | |
H15A | −0.2906 | −0.2448 | −0.4579 | 0.037* | |
H15B | −0.2492 | −0.2456 | −0.5812 | 0.037* | |
C16 | −0.3220 (4) | −0.542 (2) | −0.6186 (10) | 0.035 (2) | |
H16A | −0.3428 | −0.6639 | −0.5570 | 0.042* | |
H16B | −0.3015 | −0.6647 | −0.6802 | 0.042* | |
C17 | −0.3737 (4) | −0.364 (2) | −0.7173 (10) | 0.039 (3) | |
H17A | −0.3941 | −0.2402 | −0.6560 | 0.047* | |
H17B | −0.3531 | −0.2438 | −0.7799 | 0.047* | |
C18 | −0.4255 (5) | −0.544 (2) | −0.8140 (12) | 0.051 (3) | |
H18A | −0.4082 | −0.6263 | −0.8930 | 0.076* | |
H18B | −0.4619 | −0.4262 | −0.8539 | 0.076* | |
H18C | −0.4390 | −0.6936 | −0.7559 | 0.076* | |
O21 | 0.0801 (3) | 0.0793 (14) | 0.4393 (6) | 0.0314 (15) | |
O22 | 0.0214 (3) | 0.0339 (13) | 0.2158 (6) | 0.0277 (15) | |
C21 | 0.0718 (4) | 0.1216 (19) | 0.3022 (9) | 0.027 (2) | |
C22 | 0.1229 (5) | 0.288 (2) | 0.2438 (10) | 0.032 (3) | |
H22A | 0.1400 | 0.1680 | 0.1752 | 0.038* | |
H22B | 0.1024 | 0.4510 | 0.1891 | 0.038* | |
C23 | 0.1787 (5) | 0.394 (2) | 0.3593 (10) | 0.036 (3) | |
H23A | 0.1981 | 0.2347 | 0.4190 | 0.043* | |
H23B | 0.1628 | 0.5282 | 0.4236 | 0.043* | |
C24 | 0.2295 (4) | 0.538 (2) | 0.2896 (10) | 0.036 (2) | |
H24A | 0.2106 | 0.7026 | 0.2341 | 0.043* | |
H24B | 0.2435 | 0.4065 | 0.2211 | 0.043* | |
C25 | 0.2878 (4) | 0.632 (2) | 0.4039 (10) | 0.041 (3) | |
H25A | 0.3049 | 0.4679 | 0.4630 | 0.049* | |
H25B | 0.2738 | 0.7700 | 0.4690 | 0.049* | |
C26 | 0.3418 (4) | 0.763 (2) | 0.3369 (10) | 0.042 (3) | |
H26A | 0.3540 | 0.6278 | 0.2677 | 0.050* | |
H26B | 0.3251 | 0.9318 | 0.2818 | 0.050* | |
C27 | 0.4020 (5) | 0.844 (3) | 0.4491 (10) | 0.045 (3) | |
H27A | 0.4182 | 0.6760 | 0.5051 | 0.055* | |
H27B | 0.3899 | 0.9814 | 0.5173 | 0.055* | |
C28 | 0.4565 (5) | 0.971 (3) | 0.3830 (12) | 0.063 (4) | |
H28A | 0.4736 | 0.8277 | 0.3275 | 0.095* | |
H28B | 0.4901 | 1.0393 | 0.4608 | 0.095* | |
H28C | 0.4400 | 1.1270 | 0.3192 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.0333 (5) | 0.0212 (4) | 0.0168 (4) | 0.0002 (10) | 0.0014 (3) | −0.0011 (10) |
O11 | 0.049 (5) | 0.015 (3) | 0.021 (4) | −0.002 (3) | −0.007 (3) | −0.001 (3) |
O12 | 0.036 (4) | 0.014 (3) | 0.030 (4) | −0.005 (3) | 0.003 (3) | −0.006 (3) |
C11 | 0.035 (5) | 0.025 (6) | 0.020 (5) | −0.004 (5) | 0.007 (4) | 0.004 (4) |
C12 | 0.034 (5) | 0.021 (5) | 0.028 (5) | 0.000 (5) | 0.001 (4) | 0.004 (5) |
C13 | 0.038 (6) | 0.020 (6) | 0.032 (5) | 0.001 (4) | 0.003 (4) | 0.001 (4) |
C14 | 0.038 (6) | 0.041 (6) | 0.018 (5) | 0.006 (5) | −0.003 (4) | −0.004 (5) |
C15 | 0.033 (5) | 0.035 (6) | 0.023 (5) | 0.002 (4) | 0.002 (4) | 0.002 (4) |
C16 | 0.024 (5) | 0.045 (6) | 0.032 (5) | 0.008 (5) | −0.002 (4) | 0.002 (5) |
C17 | 0.032 (6) | 0.049 (7) | 0.035 (6) | 0.001 (5) | 0.003 (5) | −0.001 (5) |
C18 | 0.027 (6) | 0.065 (8) | 0.055 (7) | 0.000 (6) | −0.006 (5) | 0.009 (6) |
O21 | 0.041 (4) | 0.040 (4) | 0.014 (3) | 0.000 (3) | 0.007 (3) | 0.001 (3) |
O22 | 0.037 (4) | 0.031 (4) | 0.015 (3) | −0.001 (3) | 0.005 (3) | 0.002 (3) |
C21 | 0.027 (5) | 0.033 (6) | 0.020 (5) | 0.003 (4) | 0.000 (4) | −0.003 (4) |
C22 | 0.038 (6) | 0.026 (7) | 0.031 (6) | −0.011 (5) | 0.006 (5) | 0.000 (5) |
C23 | 0.039 (6) | 0.044 (8) | 0.023 (5) | 0.002 (5) | 0.004 (5) | 0.002 (5) |
C24 | 0.030 (5) | 0.048 (7) | 0.029 (5) | 0.000 (5) | 0.003 (4) | −0.001 (5) |
C25 | 0.041 (6) | 0.056 (8) | 0.026 (6) | −0.008 (5) | 0.002 (5) | 0.001 (5) |
C26 | 0.051 (7) | 0.045 (7) | 0.030 (5) | −0.011 (6) | 0.006 (5) | 0.004 (5) |
C27 | 0.039 (6) | 0.065 (8) | 0.029 (6) | −0.011 (6) | −0.003 (5) | 0.006 (5) |
C28 | 0.043 (7) | 0.096 (11) | 0.045 (7) | −0.019 (7) | −0.006 (6) | 0.000 (7) |
Zn—O12 | 1.965 (6) | C18—H18B | 0.9600 |
Zn—O22 | 1.966 (5) | C18—H18C | 0.9600 |
Zn—O11i | 1.971 (6) | O21—C21 | 1.262 (10) |
Zn—O21ii | 1.988 (6) | O21—Zniv | 1.988 (6) |
O11—C11 | 1.272 (11) | O22—C21 | 1.267 (10) |
O11—Zniii | 1.971 (6) | C21—C22 | 1.514 (11) |
O12—C11 | 1.242 (11) | C22—C23 | 1.510 (11) |
C11—C12 | 1.533 (11) | C22—H22A | 0.9700 |
C12—C13 | 1.516 (11) | C22—H22B | 0.9700 |
C12—H12A | 0.9700 | C23—C24 | 1.513 (12) |
C12—H12B | 0.9700 | C23—H23A | 0.9700 |
C13—C14 | 1.517 (11) | C23—H23B | 0.9700 |
C13—H13A | 0.9700 | C24—C25 | 1.521 (11) |
C13—H13B | 0.9700 | C24—H24A | 0.9700 |
C14—C15 | 1.528 (11) | C24—H24B | 0.9700 |
C14—H14A | 0.9700 | C25—C26 | 1.529 (8) |
C14—H14B | 0.9700 | C25—H25A | 0.9700 |
C15—C16 | 1.519 (11) | C25—H25B | 0.9700 |
C15—H15A | 0.9700 | C26—C27 | 1.524 (11) |
C15—H15B | 0.9700 | C26—H26A | 0.9700 |
C16—C17 | 1.526 (11) | C26—H26B | 0.9700 |
C16—H16A | 0.9700 | C27—C28 | 1.524 (12) |
C16—H16B | 0.9700 | C27—H27A | 0.9700 |
C17—C18 | 1.525 (11) | C27—H27B | 0.9700 |
C17—H17A | 0.9700 | C28—H28A | 0.9600 |
C17—H17B | 0.9700 | C28—H28B | 0.9600 |
C18—H18A | 0.9600 | C28—H28C | 0.9600 |
O12—Zn—O22 | 112.8 (3) | C17—C18—H18C | 109.5 |
O12—Zn—O11i | 105.1 (3) | H18A—C18—H18C | 109.5 |
O22—Zn—O11i | 102.5 (2) | H18B—C18—H18C | 109.5 |
O12—Zn—O21ii | 115.6 (3) | C21—O21—Zniv | 112.0 (6) |
O22—Zn—O21ii | 103.2 (2) | C21—O22—Zn | 128.3 (5) |
O11i—Zn—O21ii | 117.1 (3) | O21—C21—O22 | 121.1 (8) |
C11—O11—Zniii | 133.0 (6) | O21—C21—C22 | 118.2 (8) |
C11—O12—Zn | 114.3 (6) | O22—C21—C22 | 120.7 (7) |
O12—C11—O11 | 120.4 (8) | C23—C22—C21 | 115.3 (8) |
O12—C11—C12 | 118.9 (8) | C23—C22—H22A | 108.4 |
O11—C11—C12 | 120.7 (8) | C21—C22—H22A | 108.4 |
C13—C12—C11 | 114.5 (8) | C23—C22—H22B | 108.5 |
C13—C12—H12A | 108.6 | C21—C22—H22B | 108.5 |
C11—C12—H12A | 108.6 | H22A—C22—H22B | 107.5 |
C13—C12—H12B | 108.6 | C22—C23—C24 | 111.3 (7) |
C11—C12—H12B | 108.6 | C22—C23—H23A | 109.4 |
H12A—C12—H12B | 107.6 | C24—C23—H23A | 109.4 |
C12—C13—C14 | 111.3 (7) | C22—C23—H23B | 109.4 |
C12—C13—H13A | 109.4 | C24—C23—H23B | 109.4 |
C14—C13—H13A | 109.4 | H23A—C23—H23B | 108.0 |
C12—C13—H13B | 109.4 | C23—C24—C25 | 112.0 (7) |
C14—C13—H13B | 109.4 | C23—C24—H24A | 109.2 |
H13A—C13—H13B | 108.0 | C25—C24—H24A | 109.2 |
C13—C14—C15 | 112.9 (8) | C23—C24—H24B | 109.2 |
C13—C14—H14A | 109.0 | C25—C24—H24B | 109.2 |
C15—C14—H14A | 109.0 | H24A—C24—H24B | 107.9 |
C13—C14—H14B | 109.0 | C24—C25—C26 | 113.5 (7) |
C15—C14—H14B | 109.0 | C24—C25—H25A | 108.9 |
H14A—C14—H14B | 107.8 | C26—C25—H25A | 108.9 |
C16—C15—C14 | 112.9 (8) | C24—C25—H25B | 108.9 |
C16—C15—H15A | 109.0 | C26—C25—H25B | 108.9 |
C14—C15—H15A | 109.0 | H25A—C25—H25B | 107.7 |
C16—C15—H15B | 109.0 | C27—C26—C25 | 114.4 (7) |
C14—C15—H15B | 109.0 | C27—C26—H26A | 108.7 |
H15A—C15—H15B | 107.8 | C25—C26—H26A | 108.7 |
C15—C16—C17 | 114.0 (8) | C27—C26—H26B | 108.7 |
C15—C16—H16A | 108.7 | C25—C26—H26B | 108.7 |
C17—C16—H16A | 108.7 | H26A—C26—H26B | 107.6 |
C15—C16—H16B | 108.7 | C26—C27—C28 | 114.7 (8) |
C17—C16—H16B | 108.7 | C26—C27—H27A | 108.6 |
H16A—C16—H16B | 107.6 | C28—C27—H27A | 108.6 |
C18—C17—C16 | 113.1 (8) | C26—C27—H27B | 108.6 |
C18—C17—H17A | 109.0 | C28—C27—H27B | 108.6 |
C16—C17—H17A | 109.0 | H27A—C27—H27B | 107.6 |
C18—C17—H17B | 109.0 | C27—C28—H28A | 109.5 |
C16—C17—H17B | 109.0 | C27—C28—H28B | 109.5 |
H17A—C17—H17B | 107.8 | H28A—C28—H28B | 109.5 |
C17—C18—H18A | 109.5 | C27—C28—H28C | 109.5 |
C17—C18—H18B | 109.5 | H28A—C28—H28C | 109.5 |
H18A—C18—H18B | 109.5 | H28B—C28—H28C | 109.5 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y, z−1/2; (iii) x, y−1, z; (iv) x, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C8H15O2)2] |
Mr | 351.79 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 150 |
a, b, c (Å) | 21.093 (2), 4.6905 (3), 9.2544 (9) |
β (°) | 101.323 (3) |
V (Å3) | 897.78 (14) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.38 |
Crystal size (mm) | 0.30 × 0.20 × 0.02 |
Data collection | |
Diffractometer | Nonius CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) fitted by spherical harmonic functions (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.751, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14913, 2984, 2231 |
Rint | 0.095 |
(sin θ/λ)max (Å−1) | 0.589 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.167, 1.00 |
No. of reflections | 2984 |
No. of parameters | 191 |
No. of restraints | 16 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.57, −0.66 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.02 (3) |
Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ATOMS (Dowty, 1995), WINWORD Version 5.0.
Zn—O12 | 1.965 (6) | Zn—O21ii | 1.988 (6) |
Zn—O22 | 1.966 (5) | O11—C11 | 1.272 (11) |
Zn—O11i | 1.971 (6) | O12—C11 | 1.242 (11) |
O12—Zn—O22 | 112.8 (3) | O12—C11—O11 | 120.4 (8) |
O12—Zn—O11i | 105.1 (3) | O12—C11—C12 | 118.9 (8) |
O22—Zn—O11i | 102.5 (2) | O11—C11—C12 | 120.7 (8) |
O12—Zn—O21ii | 115.6 (3) | C21—O21—Zniv | 112.0 (6) |
O22—Zn—O21ii | 103.2 (2) | C21—O22—Zn | 128.3 (5) |
O11i—Zn—O21ii | 117.1 (3) | O21—C21—O22 | 121.1 (8) |
C11—O11—Zniii | 133.0 (6) | O21—C21—C22 | 118.2 (8) |
C11—O12—Zn | 114.3 (6) | O22—C21—C22 | 120.7 (7) |
Symmetry codes: (i) x, y+1, z; (ii) x, −y, z−1/2; (iii) x, y−1, z; (iv) x, −y, z+1/2. |
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The elucidation of the structure of the title compound, (I), follows that already performed for zinc heptanoate, (II) (Peultier et al., 1999). It was undertaken to characterize as well as possible these metal soaps which protect zinc surfaces against corrosion, and to understand the evolution of the structural properties in the Zn(CnH2n-1O2)2 series according to n, the number of C atoms in the aliphatic chain. \scheme
Compound (I) clearly shows the structural features of the previously known members of the series, namely, n = 2 (acetate; Clegg et al., 1987; Frada, 1992), n = 3 (propionate; Clegg et al., 1986), n = 4 (butanoate; Blair et al., 1993) and n = 6 (hexanoate; Segedin et al., 1999). The structure is layered, as shown in Fig. 1. Each Zn atom is tetrahedrally coordinated by O atoms belonging to four different octanoate groups (Fig. 2). The Zn tetrahedra are connected by syn-anti bridges of the octanoate groups, thus forming layers parallel to (100). The chains constituted by the C2n atoms form an angle of approximately 60°, confirming the tendency of these angles to decrease when n increases (Peultier et al., 1999).
It is mainly the stacking mode of the layers which varies according to n. For example, the addition of a C atom in going from zinc heptanoate [(II)] to zinc octanoate [(I)] results in the structure changing from one in which the planes containing the C2n chains of two adjacent layers form an angle of approximately 120° [(II)] to one in which they are parallel [(I)]. The structure of (I) (Pc) can be deduced from that of (II) [Pbc21, a = 4.7651 (6), b = 9.3404 (15) and c = 37.066 (6) Å] by carrying out a rotation of 180° of every other layer around the c axis, followed by a translation of 4.14 Å along the b axis. This modification in stacking involves the loss of the 21 axis parallel with the c axis and of the c glide mirror perpendicular to the b axis, but preserves the b glide mirror perpendicular to the a axis. According to the orientation used to describe the structure of (I), the element of symmetry which is preserved is a c glide mirror perpendicular to the monoclinic b axis, which for (I) leads to a noncentrosymmetric and monoclinic structure (Pc).