metal-organic compounds
The title compound, [Sn(CH3)3(C16H12ClO3)]n, forms polymeric chains incorporating both O atoms of the propenoate ligand. The coordination geometry around the Sn atom is distorted trigonal bipyramidal. The three methyl C atoms occupy the equatorial positions with almost identical Sn—C distances [2.115 (3)–2.120 (3) Å] and O atoms from two symmetry-related ligands are in the axial positions with significantly different Sn—O distances [2.150 (2) and 2.430 (2) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015314/lh6235sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015314/lh6235Isup2.hkl |
CCDC reference: 248719
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 (Sheldrick, 1997).
Crystal data top
[Sn(CH3)3(C16H12ClO3)] | F(000) = 904 |
Mr = 451.50 | Dx = 1.587 Mg m−3 |
Monoclinic, P21/c | Melting point: 399-401 K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.512 (2) Å | Cell parameters from 7498 reflections |
b = 10.424 (2) Å | θ = 3.3–27.5° |
c = 19.421 (4) Å | µ = 1.51 mm−1 |
β = 101.118 (14)° | T = 173 K |
V = 1889.5 (7) Å3 | Block, colorless |
Z = 4 | 0.14 × 0.14 × 0.09 mm |
Data collection top
Nonius KappaCCD diffractometer | 4314 independent reflections |
Radiation source: fine-focus sealed tube | 3546 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω and φ scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −12→12 |
Tmin = 0.817, Tmax = 0.876 | k = −13→13 |
7498 measured reflections | l = −25→25 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0378P)2 + 0.4627P] where P = (Fo2 + 2Fc2)/3 |
4314 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 1.04 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.483173 (18) | 0.284904 (16) | 0.236351 (8) | 0.02404 (8) | |
Cl1 | 0.22030 (9) | 1.11811 (7) | −0.01816 (4) | 0.04398 (19) | |
O1 | 0.4141 (2) | 0.41074 (18) | 0.14861 (9) | 0.0414 (5) | |
O2 | 0.4456 (2) | 0.61528 (18) | 0.17821 (9) | 0.0378 (5) | |
O3 | −0.0766 (2) | 0.5040 (2) | −0.25098 (10) | 0.0460 (5) | |
C1 | 0.3453 (3) | 0.1467 (3) | 0.17871 (14) | 0.0358 (6) | |
H1A | 0.3854 | 0.1181 | 0.1384 | 0.054* | |
H1B | 0.2508 | 0.1850 | 0.1620 | 0.054* | |
H1C | 0.3361 | 0.0732 | 0.2090 | 0.054* | |
C2 | 0.4088 (3) | 0.3880 (3) | 0.31636 (13) | 0.0315 (6) | |
H2A | 0.4823 | 0.3866 | 0.3593 | 0.047* | |
H2B | 0.3209 | 0.3480 | 0.3254 | 0.047* | |
H2C | 0.3889 | 0.4770 | 0.3013 | 0.047* | |
C3 | 0.7004 (3) | 0.2891 (3) | 0.22600 (16) | 0.0393 (7) | |
H3A | 0.7441 | 0.2050 | 0.2384 | 0.059* | |
H3B | 0.7517 | 0.3546 | 0.2574 | 0.059* | |
H3C | 0.7062 | 0.3096 | 0.1774 | 0.059* | |
C4 | 0.4012 (3) | 0.5302 (2) | 0.13597 (12) | 0.0257 (5) | |
C5 | 0.3235 (3) | 0.5649 (2) | 0.06277 (12) | 0.0233 (5) | |
C6 | 0.3006 (3) | 0.7036 (2) | 0.04537 (12) | 0.0232 (5) | |
C7 | 0.3706 (3) | 0.7601 (3) | −0.00363 (14) | 0.0274 (6) | |
H7 | 0.4356 | 0.7105 | −0.0241 | 0.033* | |
C8 | 0.3471 (3) | 0.8876 (3) | −0.02305 (14) | 0.0327 (6) | |
H8 | 0.3952 | 0.9254 | −0.0565 | 0.039* | |
C9 | 0.2531 (3) | 0.9580 (2) | 0.00707 (13) | 0.0307 (6) | |
C10 | 0.1819 (3) | 0.9051 (3) | 0.05580 (13) | 0.0327 (6) | |
H10 | 0.1162 | 0.9551 | 0.0756 | 0.039* | |
C11 | 0.2075 (3) | 0.7782 (2) | 0.07555 (14) | 0.0297 (6) | |
H11 | 0.1610 | 0.7418 | 0.1100 | 0.036* | |
C12 | 0.2818 (3) | 0.4715 (2) | 0.01621 (12) | 0.0265 (5) | |
H12 | 0.3140 | 0.3875 | 0.0302 | 0.032* | |
C13 | 0.1916 (3) | 0.4834 (2) | −0.05431 (12) | 0.0273 (6) | |
C14 | 0.0741 (3) | 0.5665 (3) | −0.06851 (13) | 0.0318 (6) | |
H14 | 0.0546 | 0.6221 | −0.0327 | 0.038* | |
C15 | −0.0138 (3) | 0.5687 (3) | −0.13400 (14) | 0.0350 (6) | |
H15 | −0.0949 | 0.6237 | −0.1425 | 0.042* | |
C16 | 0.0158 (3) | 0.4910 (3) | −0.18743 (13) | 0.0322 (6) | |
C17 | 0.1297 (3) | 0.4074 (3) | −0.17468 (13) | 0.0335 (6) | |
H17 | 0.1496 | 0.3533 | −0.2110 | 0.040* | |
C18 | 0.2159 (3) | 0.4028 (3) | −0.10791 (13) | 0.0291 (6) | |
H18 | 0.2929 | 0.3433 | −0.0988 | 0.035* | |
C19 | −0.0401 (4) | 0.4399 (4) | −0.30948 (14) | 0.0552 (10) | |
H19A | 0.0555 | 0.4671 | −0.3154 | 0.083* | |
H19B | −0.1102 | 0.4613 | −0.3518 | 0.083* | |
H19C | −0.0403 | 0.3470 | −0.3017 | 0.083* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03089 (12) | 0.01848 (11) | 0.02058 (11) | 0.00063 (7) | −0.00046 (7) | −0.00023 (6) |
Cl1 | 0.0664 (5) | 0.0198 (3) | 0.0402 (4) | 0.0004 (3) | −0.0037 (3) | 0.0053 (3) |
O1 | 0.0709 (15) | 0.0229 (10) | 0.0245 (9) | 0.0053 (10) | −0.0055 (9) | 0.0040 (8) |
O2 | 0.0539 (13) | 0.0266 (10) | 0.0269 (9) | −0.0029 (9) | −0.0068 (9) | −0.0056 (8) |
O3 | 0.0377 (12) | 0.0674 (15) | 0.0274 (10) | 0.0017 (11) | −0.0075 (8) | 0.0034 (10) |
C1 | 0.0398 (16) | 0.0273 (15) | 0.0355 (14) | −0.0009 (13) | −0.0051 (12) | −0.0030 (12) |
C2 | 0.0394 (16) | 0.0250 (14) | 0.0304 (13) | 0.0024 (12) | 0.0070 (11) | −0.0004 (11) |
C3 | 0.0393 (17) | 0.0408 (19) | 0.0392 (16) | −0.0002 (13) | 0.0110 (13) | 0.0011 (13) |
C4 | 0.0311 (14) | 0.0224 (13) | 0.0231 (11) | 0.0017 (11) | 0.0041 (10) | 0.0010 (11) |
C5 | 0.0259 (13) | 0.0208 (12) | 0.0223 (11) | −0.0002 (10) | 0.0026 (9) | 0.0027 (10) |
C6 | 0.0287 (14) | 0.0204 (13) | 0.0180 (11) | −0.0021 (10) | −0.0014 (9) | 0.0001 (9) |
C7 | 0.0289 (14) | 0.0257 (13) | 0.0267 (13) | 0.0016 (11) | 0.0035 (11) | 0.0028 (11) |
C8 | 0.0382 (16) | 0.0293 (15) | 0.0293 (14) | −0.0051 (12) | 0.0038 (11) | 0.0066 (11) |
C9 | 0.0436 (16) | 0.0184 (13) | 0.0246 (12) | −0.0008 (12) | −0.0071 (11) | 0.0024 (11) |
C10 | 0.0434 (16) | 0.0243 (14) | 0.0293 (13) | 0.0062 (12) | 0.0045 (12) | −0.0039 (11) |
C11 | 0.0389 (16) | 0.0259 (15) | 0.0245 (13) | −0.0007 (12) | 0.0068 (11) | 0.0003 (10) |
C12 | 0.0326 (14) | 0.0205 (13) | 0.0250 (12) | 0.0013 (11) | 0.0018 (10) | 0.0023 (11) |
C13 | 0.0344 (15) | 0.0220 (13) | 0.0237 (12) | −0.0033 (11) | 0.0014 (10) | 0.0000 (10) |
C14 | 0.0356 (15) | 0.0300 (15) | 0.0288 (13) | 0.0016 (12) | 0.0039 (11) | −0.0023 (11) |
C15 | 0.0293 (15) | 0.0375 (16) | 0.0357 (14) | 0.0052 (12) | 0.0000 (11) | 0.0044 (12) |
C16 | 0.0303 (15) | 0.0392 (16) | 0.0235 (12) | −0.0061 (12) | −0.0040 (10) | 0.0076 (12) |
C17 | 0.0421 (17) | 0.0357 (16) | 0.0221 (12) | −0.0023 (13) | 0.0048 (11) | −0.0011 (11) |
C18 | 0.0382 (15) | 0.0231 (13) | 0.0242 (12) | 0.0030 (11) | 0.0014 (11) | 0.0036 (11) |
C19 | 0.0415 (19) | 0.099 (3) | 0.0225 (13) | −0.0057 (19) | −0.0012 (12) | 0.0056 (17) |
Geometric parameters (Å, º) top
Sn1—C3 | 2.115 (3) | C6—C7 | 1.393 (3) |
Sn1—C1 | 2.117 (3) | C7—C8 | 1.387 (4) |
Sn1—C2 | 2.120 (3) | C7—H7 | 0.9500 |
Sn1—O1 | 2.150 (2) | C8—C9 | 1.372 (4) |
Sn1—O2i | 2.430 (2) | C8—H8 | 0.9500 |
Cl1—C9 | 1.751 (3) | C9—C10 | 1.380 (4) |
O1—C4 | 1.270 (3) | C10—C11 | 1.386 (4) |
O2—C4 | 1.227 (3) | C10—H10 | 0.9500 |
O2—Sn1ii | 2.430 (2) | C11—H11 | 0.9500 |
O3—C16 | 1.377 (3) | C12—C13 | 1.474 (3) |
O3—C19 | 1.418 (4) | C12—H12 | 0.9500 |
C1—H1A | 0.9800 | C13—C18 | 1.391 (4) |
C1—H1B | 0.9800 | C13—C14 | 1.399 (4) |
C1—H1C | 0.9800 | C14—C15 | 1.381 (4) |
C2—H2A | 0.9800 | C14—H14 | 0.9500 |
C2—H2B | 0.9800 | C15—C16 | 1.387 (4) |
C2—H2C | 0.9800 | C15—H15 | 0.9500 |
C3—H3A | 0.9800 | C16—C17 | 1.375 (4) |
C3—H3B | 0.9800 | C17—C18 | 1.395 (4) |
C3—H3C | 0.9800 | C17—H17 | 0.9500 |
C4—C5 | 1.514 (3) | C18—H18 | 0.9500 |
C5—C12 | 1.336 (3) | C19—H19A | 0.9800 |
C5—C6 | 1.492 (3) | C19—H19B | 0.9800 |
C6—C11 | 1.390 (4) | C19—H19C | 0.9800 |
C3—Sn1—C1 | 118.73 (12) | C8—C7—H7 | 119.4 |
C3—Sn1—C2 | 121.97 (12) | C6—C7—H7 | 119.4 |
C1—Sn1—C2 | 118.20 (11) | C9—C8—C7 | 118.7 (2) |
C3—Sn1—O1 | 93.83 (11) | C9—C8—H8 | 120.7 |
C1—Sn1—O1 | 86.13 (10) | C7—C8—H8 | 120.7 |
C2—Sn1—O1 | 100.23 (9) | C8—C9—C10 | 121.7 (2) |
C3—Sn1—O2i | 86.05 (10) | C8—C9—Cl1 | 119.1 (2) |
C1—Sn1—O2i | 85.91 (9) | C10—C9—Cl1 | 119.2 (2) |
C2—Sn1—O2i | 87.52 (9) | C9—C10—C11 | 119.2 (3) |
O1—Sn1—O2i | 170.85 (7) | C9—C10—H10 | 120.4 |
C4—O1—Sn1 | 139.0 (2) | C11—C10—H10 | 120.4 |
C4—O2—Sn1ii | 176.0 (2) | C10—C11—C6 | 120.6 (2) |
C16—O3—C19 | 117.3 (2) | C10—C11—H11 | 119.7 |
Sn1—C1—H1A | 109.5 | C6—C11—H11 | 119.7 |
Sn1—C1—H1B | 109.5 | C5—C12—C13 | 127.7 (2) |
H1A—C1—H1B | 109.5 | C5—C12—H12 | 116.2 |
Sn1—C1—H1C | 109.5 | C13—C12—H12 | 116.2 |
H1A—C1—H1C | 109.5 | C18—C13—C14 | 117.9 (2) |
H1B—C1—H1C | 109.5 | C18—C13—C12 | 119.6 (2) |
Sn1—C2—H2A | 109.5 | C14—C13—C12 | 122.3 (2) |
Sn1—C2—H2B | 109.5 | C15—C14—C13 | 120.7 (3) |
H2A—C2—H2B | 109.5 | C15—C14—H14 | 119.7 |
Sn1—C2—H2C | 109.5 | C13—C14—H14 | 119.7 |
H2A—C2—H2C | 109.5 | C14—C15—C16 | 120.3 (3) |
H2B—C2—H2C | 109.5 | C14—C15—H15 | 119.8 |
Sn1—C3—H3A | 109.5 | C16—C15—H15 | 119.8 |
Sn1—C3—H3B | 109.5 | C17—C16—O3 | 124.6 (3) |
H3A—C3—H3B | 109.5 | C17—C16—C15 | 120.1 (2) |
Sn1—C3—H3C | 109.5 | O3—C16—C15 | 115.2 (3) |
H3A—C3—H3C | 109.5 | C16—C17—C18 | 119.4 (3) |
H3B—C3—H3C | 109.5 | C16—C17—H17 | 120.3 |
O2—C4—O1 | 124.8 (2) | C18—C17—H17 | 120.3 |
O2—C4—C5 | 119.9 (2) | C13—C18—C17 | 121.5 (3) |
O1—C4—C5 | 115.3 (2) | C13—C18—H18 | 119.3 |
C12—C5—C6 | 122.8 (2) | C17—C18—H18 | 119.3 |
C12—C5—C4 | 119.3 (2) | O3—C19—H19A | 109.5 |
C6—C5—C4 | 117.9 (2) | O3—C19—H19B | 109.5 |
C11—C6—C7 | 118.6 (2) | H19A—C19—H19B | 109.5 |
C11—C6—C5 | 121.6 (2) | O3—C19—H19C | 109.5 |
C7—C6—C5 | 119.8 (2) | H19A—C19—H19C | 109.5 |
C8—C7—C6 | 121.2 (2) | H19B—C19—H19C | 109.5 |
C3—Sn1—O1—C4 | −87.5 (3) | C9—C10—C11—C6 | −1.8 (4) |
C1—Sn1—O1—C4 | 153.9 (3) | C7—C6—C11—C10 | 1.8 (4) |
C2—Sn1—O1—C4 | 36.0 (3) | C5—C6—C11—C10 | −176.5 (2) |
Sn1—O1—C4—O2 | 8.3 (5) | C6—C5—C12—C13 | −9.3 (4) |
Sn1—O1—C4—C5 | −171.3 (2) | C4—C5—C12—C13 | 172.5 (2) |
O2—C4—C5—C12 | 176.8 (2) | C5—C12—C13—C18 | 146.6 (3) |
O1—C4—C5—C12 | −3.6 (4) | C5—C12—C13—C14 | −38.6 (4) |
O2—C4—C5—C6 | −1.5 (4) | C18—C13—C14—C15 | −0.5 (4) |
O1—C4—C5—C6 | 178.1 (2) | C12—C13—C14—C15 | −175.5 (3) |
C12—C5—C6—C11 | 112.9 (3) | C13—C14—C15—C16 | −2.0 (4) |
C4—C5—C6—C11 | −68.8 (3) | C19—O3—C16—C17 | −9.1 (4) |
C12—C5—C6—C7 | −65.3 (4) | C19—O3—C16—C15 | 171.7 (3) |
C4—C5—C6—C7 | 112.9 (3) | C14—C15—C16—C17 | 2.6 (4) |
C11—C6—C7—C8 | −0.9 (4) | C14—C15—C16—O3 | −178.1 (3) |
C5—C6—C7—C8 | 177.4 (2) | O3—C16—C17—C18 | −180.0 (3) |
C6—C7—C8—C9 | 0.0 (4) | C15—C16—C17—C18 | −0.7 (4) |
C7—C8—C9—C10 | 0.0 (4) | C14—C13—C18—C17 | 2.4 (4) |
C7—C8—C9—Cl1 | −178.9 (2) | C12—C13—C18—C17 | 177.5 (2) |
C8—C9—C10—C11 | 0.9 (4) | C16—C17—C18—C13 | −1.8 (4) |
Cl1—C9—C10—C11 | 179.8 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |