metal-organic compounds
The crystal structure of the title compound, [Sn(CH3)3(C15H10ClO2)]n, contains polymeric chains along the b axis. The geometry around the Sn atom is distorted trigonal bipyramidal, wherein three methyl groups are bonded to the Sn atom at equatorial positions with essentially identical bond distances [mean Sn—C = 2.119 (6) Å] and two O atoms of the carboxylate ligand are bonded asymmetrically with significantly different Sn—O distances of 2.159 (2) and 2.351 (2) Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021774/lh6264sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021774/lh6264Isup2.hkl |
CCDC reference: 252758
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(C15H10ClO2)] | F(000) = 840 |
Mr = 421.47 | Dx = 1.560 Mg m−3 |
Monoclinic, P21/c | Melting point: 389-391 K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.350 (3) Å | Cell parameters from 6771 reflections |
b = 10.454 (3) Å | θ = 3.0–27.5° |
c = 18.902 (7) Å | µ = 1.58 mm−1 |
β = 103.764 (14)° | T = 173 K |
V = 1794.5 (10) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.17 × 0.12 mm |
Data collection top
Nonius KappaCCD diffractometer | 4051 independent reflections |
Radiation source: fine-focus sealed tube | 3038 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω and φ scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −12→12 |
Tmin = 0.743, Tmax = 0.833 | k = −13→11 |
6771 measured reflections | l = −24→24 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0297P)2 + 0.4273P] where P = (Fo2 + 2Fc2)/3 |
4051 reflections | (Δ/σ)max = 0.001 |
202 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.69 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.52240 (2) | 0.216965 (19) | 0.259974 (11) | 0.02749 (9) | |
Cl1 | 1.05567 (11) | 0.03579 (9) | 0.80323 (5) | 0.0472 (2) | |
O1 | 0.6218 (4) | 0.0860 (2) | 0.34601 (13) | 0.0695 (10) | |
O2 | 0.5729 (3) | −0.1156 (2) | 0.32051 (13) | 0.0600 (8) | |
C1 | 0.6729 (4) | 0.3517 (3) | 0.32044 (19) | 0.0428 (9) | |
H1A | 0.7712 | 0.3132 | 0.3346 | 0.064* | |
H1B | 0.6409 | 0.3765 | 0.3642 | 0.064* | |
H1C | 0.6762 | 0.4276 | 0.2904 | 0.064* | |
C2 | 0.3099 (4) | 0.1961 (4) | 0.2785 (2) | 0.0558 (11) | |
H2A | 0.2383 | 0.1834 | 0.2319 | 0.084* | |
H2B | 0.2843 | 0.2732 | 0.3023 | 0.084* | |
H2C | 0.3083 | 0.1218 | 0.3100 | 0.084* | |
C3 | 0.5796 (4) | 0.1163 (3) | 0.17309 (18) | 0.0374 (8) | |
H3A | 0.6671 | 0.1555 | 0.1621 | 0.056* | |
H3B | 0.4975 | 0.1202 | 0.1298 | 0.056* | |
H3C | 0.6005 | 0.0268 | 0.1872 | 0.056* | |
C4 | 0.6261 (4) | −0.0309 (3) | 0.36253 (18) | 0.0348 (8) | |
C5 | 0.7055 (4) | −0.0630 (3) | 0.44025 (16) | 0.0282 (7) | |
C6 | 0.7564 (4) | 0.0331 (3) | 0.48548 (17) | 0.0340 (8) | |
H6 | 0.7383 | 0.1162 | 0.4649 | 0.041* | |
C7 | 0.7179 (4) | −0.2002 (3) | 0.46138 (16) | 0.0303 (8) | |
C8 | 0.6410 (5) | −0.2485 (3) | 0.50984 (18) | 0.0418 (9) | |
H8 | 0.5776 | −0.1940 | 0.5287 | 0.050* | |
C9 | 0.6558 (6) | −0.3751 (4) | 0.5308 (2) | 0.0596 (13) | |
H9 | 0.6021 | −0.4072 | 0.5638 | 0.072* | |
C10 | 0.7471 (6) | −0.4546 (4) | 0.5045 (2) | 0.0712 (17) | |
H10 | 0.7575 | −0.5415 | 0.5197 | 0.085* | |
C11 | 0.8235 (5) | −0.4095 (4) | 0.4564 (2) | 0.0563 (12) | |
H11 | 0.8858 | −0.4653 | 0.4377 | 0.068* | |
C12 | 0.8100 (4) | −0.2822 (3) | 0.43482 (19) | 0.0399 (9) | |
H12 | 0.8639 | −0.2510 | 0.4017 | 0.048* | |
C13 | 0.8365 (4) | 0.0299 (3) | 0.56253 (17) | 0.0320 (8) | |
C14 | 0.8229 (5) | 0.1336 (3) | 0.6056 (2) | 0.0530 (11) | |
H14 | 0.7654 | 0.2048 | 0.5842 | 0.064* | |
C15 | 0.8915 (5) | 0.1366 (4) | 0.67982 (19) | 0.0537 (11) | |
H15 | 0.8787 | 0.2079 | 0.7088 | 0.064* | |
C16 | 0.9768 (4) | 0.0362 (3) | 0.70999 (17) | 0.0322 (8) | |
C17 | 0.9988 (4) | −0.0660 (3) | 0.66778 (18) | 0.0377 (8) | |
H17 | 1.0618 | −0.1342 | 0.6889 | 0.045* | |
C18 | 0.9286 (4) | −0.0693 (3) | 0.59430 (18) | 0.0366 (8) | |
H18 | 0.9438 | −0.1401 | 0.5654 | 0.044* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03482 (15) | 0.02258 (13) | 0.02282 (13) | 0.00065 (9) | 0.00242 (9) | −0.00168 (9) |
Cl1 | 0.0426 (5) | 0.0646 (6) | 0.0285 (4) | 0.0043 (4) | −0.0033 (4) | −0.0027 (4) |
O1 | 0.129 (3) | 0.0296 (14) | 0.0312 (14) | 0.0067 (15) | −0.0188 (16) | 0.0059 (12) |
O2 | 0.096 (2) | 0.0322 (13) | 0.0335 (14) | −0.0110 (14) | −0.0207 (15) | −0.0042 (11) |
C1 | 0.042 (2) | 0.0335 (18) | 0.045 (2) | −0.0013 (16) | −0.0036 (17) | −0.0133 (17) |
C2 | 0.047 (3) | 0.069 (3) | 0.055 (3) | −0.012 (2) | 0.020 (2) | −0.019 (2) |
C3 | 0.040 (2) | 0.0351 (18) | 0.0375 (19) | −0.0015 (15) | 0.0103 (17) | −0.0063 (15) |
C4 | 0.043 (2) | 0.0309 (18) | 0.0295 (18) | 0.0055 (15) | 0.0063 (16) | 0.0012 (15) |
C5 | 0.0318 (18) | 0.0274 (16) | 0.0238 (16) | 0.0015 (13) | 0.0033 (14) | −0.0003 (14) |
C6 | 0.048 (2) | 0.0257 (17) | 0.0262 (17) | 0.0002 (14) | 0.0044 (16) | 0.0050 (14) |
C7 | 0.040 (2) | 0.0259 (16) | 0.0189 (16) | −0.0019 (14) | −0.0058 (14) | −0.0005 (13) |
C8 | 0.058 (3) | 0.0401 (19) | 0.0251 (18) | −0.0104 (17) | 0.0049 (17) | 0.0011 (15) |
C9 | 0.098 (4) | 0.044 (2) | 0.028 (2) | −0.027 (2) | −0.003 (2) | 0.0104 (18) |
C10 | 0.120 (5) | 0.025 (2) | 0.044 (3) | −0.005 (2) | −0.029 (3) | 0.0097 (19) |
C11 | 0.068 (3) | 0.035 (2) | 0.050 (3) | 0.015 (2) | −0.018 (2) | −0.010 (2) |
C12 | 0.047 (2) | 0.0343 (19) | 0.0321 (19) | 0.0048 (17) | −0.0026 (17) | −0.0054 (16) |
C13 | 0.038 (2) | 0.0295 (17) | 0.0259 (17) | −0.0028 (14) | 0.0026 (15) | −0.0014 (14) |
C14 | 0.078 (3) | 0.034 (2) | 0.036 (2) | 0.0123 (19) | −0.008 (2) | −0.0027 (17) |
C15 | 0.080 (3) | 0.040 (2) | 0.032 (2) | 0.016 (2) | −0.003 (2) | −0.0102 (17) |
C16 | 0.0288 (19) | 0.042 (2) | 0.0248 (17) | −0.0020 (14) | 0.0034 (14) | −0.0024 (15) |
C17 | 0.0322 (19) | 0.045 (2) | 0.0322 (19) | 0.0065 (16) | −0.0001 (15) | −0.0002 (16) |
C18 | 0.036 (2) | 0.0380 (18) | 0.0338 (19) | 0.0048 (15) | 0.0049 (16) | −0.0086 (15) |
Geometric parameters (Å, º) top
Sn1—C2 | 2.110 (4) | C6—H6 | 0.9500 |
Sn1—C1 | 2.123 (3) | C7—C8 | 1.388 (5) |
Sn1—C3 | 2.123 (3) | C7—C12 | 1.390 (5) |
Sn1—O1 | 2.159 (2) | C8—C9 | 1.379 (5) |
Sn1—O2i | 2.351 (2) | C8—H8 | 0.9500 |
Cl1—C16 | 1.741 (3) | C9—C10 | 1.369 (7) |
O1—C4 | 1.260 (4) | C9—H9 | 0.9500 |
O2—C4 | 1.214 (4) | C10—C11 | 1.366 (7) |
O2—Sn1ii | 2.351 (2) | C10—H10 | 0.9500 |
C1—H1A | 0.9800 | C11—C12 | 1.389 (5) |
C1—H1B | 0.9800 | C11—H11 | 0.9500 |
C1—H1C | 0.9800 | C12—H12 | 0.9500 |
C2—H2A | 0.9800 | C13—C14 | 1.379 (5) |
C2—H2B | 0.9800 | C13—C18 | 1.390 (4) |
C2—H2C | 0.9800 | C14—C15 | 1.398 (5) |
C3—H3A | 0.9800 | C14—H14 | 0.9500 |
C3—H3B | 0.9800 | C15—C16 | 1.359 (5) |
C3—H3C | 0.9800 | C15—H15 | 0.9500 |
C4—C5 | 1.517 (4) | C16—C17 | 1.378 (5) |
C5—C6 | 1.332 (4) | C17—C18 | 1.388 (4) |
C5—C7 | 1.486 (4) | C17—H17 | 0.9500 |
C6—C13 | 1.471 (4) | C18—H18 | 0.9500 |
C2—Sn1—C1 | 120.62 (15) | C13—C6—H6 | 115.2 |
C2—Sn1—C3 | 119.85 (14) | C8—C7—C12 | 118.5 (3) |
C1—Sn1—C3 | 119.24 (14) | C8—C7—C5 | 120.6 (3) |
C2—Sn1—O1 | 93.60 (16) | C12—C7—C5 | 120.9 (3) |
C1—Sn1—O1 | 84.47 (12) | C9—C8—C7 | 120.5 (4) |
C3—Sn1—O1 | 97.24 (12) | C9—C8—H8 | 119.8 |
C2—Sn1—O2i | 87.59 (15) | C7—C8—H8 | 119.8 |
C1—Sn1—O2i | 87.43 (12) | C10—C9—C8 | 120.5 (4) |
C3—Sn1—O2i | 89.69 (12) | C10—C9—H9 | 119.8 |
O1—Sn1—O2i | 171.21 (9) | C8—C9—H9 | 119.8 |
C4—O1—Sn1 | 141.7 (2) | C11—C10—C9 | 120.2 (4) |
C4—O2—Sn1ii | 178.0 (3) | C11—C10—H10 | 119.9 |
Sn1—C1—H1A | 109.5 | C9—C10—H10 | 119.9 |
Sn1—C1—H1B | 109.5 | C10—C11—C12 | 120.0 (4) |
H1A—C1—H1B | 109.5 | C10—C11—H11 | 120.0 |
Sn1—C1—H1C | 109.5 | C12—C11—H11 | 120.0 |
H1A—C1—H1C | 109.5 | C11—C12—C7 | 120.4 (4) |
H1B—C1—H1C | 109.5 | C11—C12—H12 | 119.8 |
Sn1—C2—H2A | 109.5 | C7—C12—H12 | 119.8 |
Sn1—C2—H2B | 109.5 | C14—C13—C18 | 117.8 (3) |
H2A—C2—H2B | 109.5 | C14—C13—C6 | 118.0 (3) |
Sn1—C2—H2C | 109.5 | C18—C13—C6 | 124.2 (3) |
H2A—C2—H2C | 109.5 | C13—C14—C15 | 121.7 (3) |
H2B—C2—H2C | 109.5 | C13—C14—H14 | 119.2 |
Sn1—C3—H3A | 109.5 | C15—C14—H14 | 119.2 |
Sn1—C3—H3B | 109.5 | C16—C15—C14 | 119.2 (3) |
H3A—C3—H3B | 109.5 | C16—C15—H15 | 120.4 |
Sn1—C3—H3C | 109.5 | C14—C15—H15 | 120.4 |
H3A—C3—H3C | 109.5 | C15—C16—C17 | 120.6 (3) |
H3B—C3—H3C | 109.5 | C15—C16—Cl1 | 119.4 (3) |
O2—C4—O1 | 124.2 (3) | C17—C16—Cl1 | 119.9 (3) |
O2—C4—C5 | 120.2 (3) | C16—C17—C18 | 119.9 (3) |
O1—C4—C5 | 115.7 (3) | C16—C17—H17 | 120.0 |
C6—C5—C7 | 124.2 (3) | C18—C17—H17 | 120.0 |
C6—C5—C4 | 118.2 (3) | C17—C18—C13 | 120.7 (3) |
C7—C5—C4 | 117.5 (3) | C17—C18—H18 | 119.6 |
C5—C6—C13 | 129.7 (3) | C13—C18—H18 | 119.6 |
C5—C6—H6 | 115.2 | ||
C2—Sn1—O1—C4 | 69.7 (5) | C8—C9—C10—C11 | −0.7 (6) |
C1—Sn1—O1—C4 | −169.9 (5) | C9—C10—C11—C12 | 0.8 (6) |
C3—Sn1—O1—C4 | −51.0 (5) | C10—C11—C12—C7 | −0.6 (6) |
Sn1—O1—C4—O2 | 9.2 (7) | C8—C7—C12—C11 | 0.2 (5) |
Sn1—O1—C4—C5 | −171.4 (3) | C5—C7—C12—C11 | 178.4 (3) |
O2—C4—C5—C6 | −177.0 (4) | C5—C6—C13—C14 | −152.5 (4) |
O1—C4—C5—C6 | 3.6 (5) | C5—C6—C13—C18 | 29.5 (6) |
O2—C4—C5—C7 | 1.5 (5) | C18—C13—C14—C15 | −3.9 (6) |
O1—C4—C5—C7 | −177.9 (3) | C6—C13—C14—C15 | 178.0 (4) |
C7—C5—C6—C13 | 1.7 (6) | C13—C14—C15—C16 | 1.7 (7) |
C4—C5—C6—C13 | −179.9 (4) | C14—C15—C16—C17 | 1.7 (6) |
C6—C5—C7—C8 | 67.4 (5) | C14—C15—C16—Cl1 | −177.0 (3) |
C4—C5—C7—C8 | −111.0 (4) | C15—C16—C17—C18 | −2.6 (6) |
C6—C5—C7—C12 | −110.7 (4) | Cl1—C16—C17—C18 | 176.1 (3) |
C4—C5—C7—C12 | 70.9 (4) | C16—C17—C18—C13 | 0.2 (5) |
C12—C7—C8—C9 | −0.1 (5) | C14—C13—C18—C17 | 3.0 (5) |
C5—C7—C8—C9 | −178.3 (3) | C6—C13—C18—C17 | −179.1 (3) |
C7—C8—C9—C10 | 0.3 (6) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2. |