metal-organic compounds
The crystal structure of catena-poly[[di-n-butyltin(IV)]-μ-glutarato], [Sn(C4H9)2(C5H6O4)], is composed of polymeric chains formed by coordination of glutarate, through both ends, to di-n-butyltin. The geometry around the hexacoordinated Sn atom is highly distorted octahedral, and may best be described as based on a skew-trapezoidal planar geometry. The symmetry-related glutarate ligands are asymmetrically coordinated to the Sn atoms, with Sn—O distances of 2.138 (2) and 2.483 (2) Å. The Sn—C distance involving the n-butyl group is 2.124 (3) Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008164/ww6019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008164/ww6019Isup2.hkl |
CCDC reference: 189297
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL 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.
(I) top
Crystal data top
[Sn(C4H9)2(C5H6O4)] | Dx = 1.555 Mg m−3 |
Mr = 363.02 | Melting point: 397 K |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9698 (4) Å | Cell parameters from 5771 reflections |
b = 15.6977 (4) Å | θ = 1.0–27.5° |
c = 9.9088 (8) Å | µ = 1.65 mm−1 |
V = 1550.76 (15) Å3 | T = 223 K |
Z = 4 | Plate, colourless |
F(000) = 736 | 0.27 × 0.24 × 0.09 mm |
Data collection top
Nonius KappaCCD diffractometer | 1727 independent reflections |
Radiation source: fine-focus sealed tube | 1462 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω and φ scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −12→11 |
Tmin = 0.664, Tmax = 0.866 | k = −20→20 |
5771 measured reflections | l = −12→12 |
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 atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + 3.123P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max = 0.001 |
1727 reflections | Δρmax = 0.54 e Å−3 |
118 parameters | Δρmin = −0.51 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0189 (17) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.2500 | 0.2500 | 0.07679 (2) | 0.01940 (15) | |
O1 | 0.1147 (2) | 0.24921 (14) | −0.09068 (18) | 0.0258 (4) | |
O2 | 0.0030 (2) | 0.23451 (14) | 0.09756 (19) | 0.0272 (5) | |
C1 | 0.2433 (3) | 0.37660 (19) | 0.1521 (3) | 0.0271 (6) | |
H1A | 0.274 (4) | 0.372 (3) | 0.236 (5) | 0.060 (4)* | |
H1B | 0.324 (5) | 0.405 (3) | 0.111 (5) | 0.060 (4)* | |
C2 | 0.1109 (4) | 0.4230 (2) | 0.1385 (4) | 0.0403 (8) | |
H2A | 0.052 (5) | 0.393 (3) | 0.189 (5) | 0.060 (4)* | |
H2B | 0.086 (5) | 0.422 (3) | 0.046 (5) | 0.060 (4)* | |
C3 | 0.1174 (5) | 0.5150 (2) | 0.1880 (4) | 0.0477 (9) | |
H3A | 0.187 (6) | 0.546 (3) | 0.144 (5) | 0.060 (4)* | |
H3B | 0.025 (5) | 0.544 (3) | 0.168 (4) | 0.060 (4)* | |
C4 | 0.1416 (8) | 0.5226 (4) | 0.3357 (6) | 0.0765 (18) | |
H4A | 0.114 (5) | 0.578 (3) | 0.369 (5) | 0.060 (4)* | |
H4B | 0.227 (6) | 0.511 (3) | 0.339 (5) | 0.060 (4)* | |
H4C | 0.085 (5) | 0.477 (3) | 0.386 (5) | 0.060 (4)* | |
C5 | 0.0023 (3) | 0.24117 (17) | −0.0265 (3) | 0.0211 (5) | |
C6 | −0.1250 (3) | 0.2415 (2) | −0.1081 (3) | 0.0251 (6) | |
H6A | −0.131 (5) | 0.189 (3) | −0.153 (4) | 0.060 (4)* | |
H6B | −0.110 (5) | 0.290 (3) | −0.174 (5) | 0.060 (4)* | |
C7 | −0.2500 | 0.2500 | −0.0242 (4) | 0.0253 (8) | |
H7A | −0.2585 | 0.1993 | 0.0347 | 0.060 (4)* | 0.50 |
H7B | −0.2415 | 0.3007 | 0.0347 | 0.060 (4)* | 0.50 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01011 (18) | 0.0300 (2) | 0.01811 (18) | 0.00025 (10) | 0.000 | 0.000 |
O1 | 0.0098 (9) | 0.0487 (12) | 0.0189 (9) | 0.0010 (9) | 0.0002 (7) | 0.0008 (9) |
O2 | 0.0127 (9) | 0.0495 (13) | 0.0193 (10) | −0.0006 (8) | −0.0007 (7) | 0.0003 (8) |
C1 | 0.0221 (14) | 0.0291 (13) | 0.0300 (15) | 0.0004 (12) | −0.0009 (13) | −0.0014 (11) |
C2 | 0.0290 (17) | 0.0383 (18) | 0.054 (2) | 0.0102 (14) | −0.0091 (16) | −0.0061 (16) |
C3 | 0.052 (3) | 0.0340 (18) | 0.057 (2) | 0.0117 (17) | −0.0078 (19) | −0.0020 (16) |
C4 | 0.107 (5) | 0.057 (3) | 0.066 (3) | 0.038 (3) | −0.018 (3) | −0.023 (2) |
C5 | 0.0112 (11) | 0.0299 (13) | 0.0223 (12) | 0.0006 (10) | 0.0010 (10) | −0.0009 (10) |
C6 | 0.0117 (13) | 0.0464 (17) | 0.0172 (12) | 0.0021 (12) | −0.0008 (10) | −0.0019 (12) |
C7 | 0.0101 (16) | 0.047 (2) | 0.0189 (17) | 0.0020 (17) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
Sn1—C1 | 2.124 (3) | C3—C4 | 1.489 (7) |
Sn1—C1i | 2.124 (3) | C3—H3A | 0.95 (5) |
Sn1—O1 | 2.138 (2) | C3—H3B | 1.05 (5) |
Sn1—O1i | 2.138 (2) | C4—H4A | 0.98 (5) |
Sn1—O2i | 2.483 (2) | C4—H4B | 0.87 (5) |
Sn1—O2 | 2.483 (2) | C4—H4C | 1.04 (5) |
O1—C5 | 1.295 (3) | C5—C6 | 1.504 (4) |
O2—C5 | 1.234 (3) | C6—C7 | 1.504 (3) |
C1—C2 | 1.514 (4) | C6—H6A | 0.94 (5) |
C1—H1A | 0.89 (5) | C6—H6B | 1.01 (5) |
C1—H1B | 1.01 (5) | C7—C6ii | 1.504 (3) |
C2—C3 | 1.526 (5) | C7—H7A | 0.9900 |
C2—H2A | 0.90 (5) | C7—H7B | 0.9900 |
C2—H2B | 0.95 (5) | ||
C1—Sn1—C1i | 138.84 (17) | H2A—C2—H2B | 111 (4) |
C1—Sn1—O1 | 104.98 (10) | C4—C3—C2 | 113.5 (4) |
C1i—Sn1—O1 | 106.68 (10) | C4—C3—H3A | 107 (3) |
C1—Sn1—O1i | 106.68 (10) | C2—C3—H3A | 112 (3) |
C1i—Sn1—O1i | 104.98 (10) | C4—C3—H3B | 107 (2) |
O1—Sn1—O1i | 78.20 (10) | C2—C3—H3B | 108 (3) |
C1—Sn1—O2i | 84.85 (10) | H3A—C3—H3B | 109 (4) |
C1i—Sn1—O2i | 91.81 (10) | C3—C4—H4A | 111 (3) |
O1—Sn1—O2i | 133.66 (7) | C3—C4—H4B | 101 (3) |
O1i—Sn1—O2i | 55.83 (7) | H4A—C4—H4B | 117 (5) |
C1—Sn1—O2 | 91.81 (10) | C3—C4—H4C | 109 (3) |
C1i—Sn1—O2 | 84.85 (10) | H4A—C4—H4C | 108 (4) |
O1—Sn1—O2 | 55.83 (7) | H4B—C4—H4C | 111 (4) |
O1i—Sn1—O2 | 133.66 (7) | O2—C5—O1 | 119.5 (2) |
O2i—Sn1—O2 | 170.49 (9) | O2—C5—C6 | 122.7 (2) |
C5—O1—Sn1 | 99.52 (15) | O1—C5—C6 | 117.8 (2) |
C5—O2—Sn1 | 85.11 (16) | C7—C6—C5 | 113.7 (2) |
C2—C1—Sn1 | 116.5 (2) | C7—C6—H6A | 107 (3) |
C2—C1—H1A | 115 (3) | C5—C6—H6A | 107 (3) |
Sn1—C1—H1A | 104 (3) | C7—C6—H6B | 114 (3) |
C2—C1—H1B | 117 (3) | C5—C6—H6B | 103 (3) |
Sn1—C1—H1B | 104 (3) | H6A—C6—H6B | 111 (4) |
H1A—C1—H1B | 98 (4) | C6ii—C7—C6 | 112.9 (3) |
C1—C2—C3 | 113.0 (3) | C6ii—C7—H7A | 109.0 |
C1—C2—H2A | 106 (3) | C6—C7—H7A | 109.0 |
C3—C2—H2A | 110 (3) | C6ii—C7—H7B | 109.0 |
C1—C2—H2B | 108 (3) | C6—C7—H7B | 109.0 |
C3—C2—H2B | 110 (3) | H7A—C7—H7B | 107.8 |
C1—Sn1—O1—C5 | −80.87 (18) | O2i—Sn1—C1—C2 | 166.1 (3) |
C1i—Sn1—O1—C5 | 72.49 (18) | O2—Sn1—C1—C2 | −22.9 (3) |
O1i—Sn1—O1—C5 | 174.8 (2) | Sn1—C1—C2—C3 | −176.8 (3) |
O2i—Sn1—O1—C5 | −178.16 (15) | C1—C2—C3—C4 | −65.8 (6) |
O2—Sn1—O1—C5 | 0.95 (15) | Sn1—O2—C5—O1 | 1.6 (2) |
C1—Sn1—O2—C5 | 105.94 (18) | Sn1—O2—C5—C6 | −177.6 (3) |
C1i—Sn1—O2—C5 | −115.17 (18) | Sn1—O1—C5—O2 | −1.8 (3) |
O1—Sn1—O2—C5 | −0.99 (15) | Sn1—O1—C5—C6 | 177.4 (2) |
O1i—Sn1—O2—C5 | −9.3 (2) | O2—C5—C6—C7 | 11.1 (4) |
C1i—Sn1—C1—C2 | −107.1 (3) | O1—C5—C6—C7 | −168.1 (2) |
O1—Sn1—C1—C2 | 32.2 (3) | C5—C6—C7—C6ii | 174.6 (3) |
O1i—Sn1—C1—C2 | 114.1 (3) |
Symmetry codes: (i) −x+1/2, −y+1/2, z; (ii) −x−1/2, −y+1/2, z. |