The polymeric title compound, [Sn(C2H5)(C6H5)2(C2H4ClO2)]n, adopts a carboxylate-bridged zigzag motif. The Sn center exhibits a trans-C3SnO2 trigonal–bipyramidal coordination.
Supporting information
CCDC reference: 621511
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.024
- wR factor = 0.061
- Data-to-parameter ratio = 21.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.03
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 26.70
From the CIF: _reflns_number_total 3368
Count of symmetry unique reflns 1782
Completeness (_total/calc) 189.00%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1586
Fraction of Friedel pairs measured 0.890
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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2003); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
catena-Poly[[diphenylethyltin(IV)]-µ-chlorocetato-
κ2O:
O']
top
Crystal data top
[Sn(C2H5)(C6H5)2(C2H4ClO2)] | F(000) = 784 |
Mr = 395.44 | Dx = 1.558 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 11887 reflections |
a = 12.265 (3) Å | θ = 2.3–26.7° |
b = 12.542 (2) Å | µ = 1.67 mm−1 |
c = 10.980 (2) Å | T = 298 K |
β = 93.59 (2)° | Prism, colorless |
V = 1685.8 (6) Å3 | 0.30 × 0.10 × 0.06 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II Imaging Plate diffractometer | 3368 independent reflections |
Radiation source: fine-focus sealed tube | 3242 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Rotation method scans | θmax = 26.7°, θmin = 2.3° |
Absorption correction: analytical (X-SHAPE; Stoe & Cie, 2005) | h = −15→15 |
Tmin = 0.763, Tmax = 0.820 | k = −15→15 |
6300 measured reflections | l = −13→13 |
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)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0348P)2 + 1.4346P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3368 reflections | Δρmax = 0.32 e Å−3 |
157 parameters | Δρmin = −0.28 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1590 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (3) |
Special details top
Experimental. 1H NMR (in CDCl3, δ): CH3 (1.46, t), CH2 (1.82, q), CH2Cl (4.16, s)
and C6H5 (7.45–7.69). 13C NMR (in CDCl3, δ): CH3 (9.54), CH2
(9.87), CH2Cl (41.76), C6H5 (128.56, 128.94, 130.28, 136.63) and CO
(138.27). 119Sn NMR (in CDCl3, δ): -3.50 and
J(119Sn–13Cipso) = 47.5 Hz. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.50000 (2) | 0.44082 (2) | 0.50000 (2) | 0.04677 (7) | |
Cl1 | 0.4201 (2) | 0.1550 (1) | 0.1878 (2) | 0.1198 (8) | |
O1 | 0.4860 (3) | 0.3352 (3) | 0.3431 (3) | 0.062 (1) | |
O2 | 0.5038 (3) | 0.4551 (2) | 0.1968 (3) | 0.059 (1) | |
C1 | 0.5018 (2) | 0.3059 (2) | 0.6185 (2) | 0.052 (1) | |
C2 | 0.5867 (2) | 0.2929 (2) | 0.7072 (3) | 0.072 (1) | |
C3 | 0.5868 (3) | 0.2061 (3) | 0.7860 (3) | 0.098 (2) | |
C4 | 0.5020 (4) | 0.1325 (3) | 0.7762 (3) | 0.100 (2) | |
C5 | 0.4171 (3) | 0.1455 (2) | 0.6875 (4) | 0.087 (2) | |
C6 | 0.4170 (2) | 0.2323 (2) | 0.6086 (3) | 0.066 (1) | |
C7 | 0.3441 (2) | 0.5121 (2) | 0.4625 (2) | 0.046 (1) | |
C8 | 0.3264 (2) | 0.5880 (2) | 0.3712 (2) | 0.059 (1) | |
C9 | 0.2253 (2) | 0.6379 (2) | 0.3547 (3) | 0.072 (1) | |
C10 | 0.1420 (2) | 0.6118 (3) | 0.4295 (3) | 0.076 (1) | |
C11 | 0.1597 (2) | 0.5359 (3) | 0.5209 (3) | 0.076 (1) | |
C12 | 0.2607 (2) | 0.4860 (2) | 0.5374 (2) | 0.060 (1) | |
C13 | 0.6517 (4) | 0.5184 (5) | 0.4772 (5) | 0.076 (1) | |
C14 | 0.7336 (6) | 0.4594 (7) | 0.4074 (8) | 0.102 (2) | |
C15 | 0.4816 (3) | 0.3650 (3) | 0.2329 (3) | 0.054 (1) | |
C16 | 0.4447 (8) | 0.2825 (4) | 0.1362 (5) | 0.110 (2) | |
H2 | 0.6434 | 0.3421 | 0.7138 | 0.087* | |
H3 | 0.6435 | 0.1974 | 0.8454 | 0.118* | |
H4 | 0.5021 | 0.0744 | 0.8289 | 0.120* | |
H5 | 0.3604 | 0.0962 | 0.6808 | 0.104* | |
H6 | 0.3602 | 0.2410 | 0.5493 | 0.079* | |
H8 | 0.3822 | 0.6054 | 0.3211 | 0.071* | |
H9 | 0.2135 | 0.6887 | 0.2936 | 0.086* | |
H10 | 0.0744 | 0.6452 | 0.4185 | 0.092* | |
H11 | 0.1039 | 0.5185 | 0.5709 | 0.091* | |
H12 | 0.2726 | 0.4352 | 0.5985 | 0.072* | |
H13a | 0.6365 | 0.5859 | 0.4364 | 0.091* | |
H13b | 0.6850 | 0.5344 | 0.5576 | 0.091* | |
H14a | 0.7984 | 0.5018 | 0.4035 | 0.153* | |
H14b | 0.7033 | 0.4454 | 0.3262 | 0.153* | |
H14c | 0.7515 | 0.3932 | 0.4477 | 0.153* | |
H16a | 0.3784 | 0.3085 | 0.0933 | 0.132* | |
H16b | 0.5002 | 0.2782 | 0.0772 | 0.132* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.0527 (1) | 0.0498 (1) | 0.0377 (1) | 0.0067 (2) | 0.0015 (1) | 0.0068 (2) |
Cl1 | 0.178 (2) | 0.060 (1) | 0.113 (1) | −0.016 (1) | −0.054 (1) | 0.006 (1) |
O1 | 0.096 (2) | 0.054 (2) | 0.035 (2) | 0.012 (2) | 0.007 (2) | 0.005 (1) |
O2 | 0.082 (2) | 0.054 (2) | 0.040 (2) | −0.002 (1) | −0.004 (1) | 0.004 (1) |
C1 | 0.069 (2) | 0.053 (2) | 0.032 (2) | 0.013 (2) | 0.006 (2) | 0.004 (2) |
C2 | 0.095 (3) | 0.067 (3) | 0.053 (3) | 0.021 (2) | −0.015 (2) | 0.005 (2) |
C3 | 0.146 (6) | 0.074 (3) | 0.073 (4) | 0.007 (4) | −0.013 (3) | 0.031 (3) |
C4 | 0.139 (6) | 0.075 (4) | 0.089 (4) | 0.028 (4) | 0.026 (4) | 0.039 (3) |
C5 | 0.109 (4) | 0.061 (3) | 0.092 (4) | −0.006 (3) | 0.019 (3) | 0.015 (3) |
C6 | 0.075 (3) | 0.058 (2) | 0.064 (3) | 0.006 (2) | 0.010 (2) | 0.010 (2) |
C7 | 0.053 (2) | 0.050 (2) | 0.034 (2) | 0.008 (2) | −0.002 (2) | −0.002 (2) |
C8 | 0.069 (2) | 0.065 (2) | 0.044 (2) | 0.0180 (19) | 0.002 (2) | 0.007 (2) |
C9 | 0.088 (3) | 0.072 (3) | 0.055 (3) | 0.029 (2) | −0.007 (2) | 0.003 (2) |
C10 | 0.068 (3) | 0.083 (3) | 0.076 (3) | 0.031 (2) | −0.012 (2) | −0.019 (3) |
C11 | 0.063 (3) | 0.091 (3) | 0.074 (3) | 0.008 (2) | 0.013 (2) | −0.012 (3) |
C12 | 0.057 (2) | 0.067 (3) | 0.057 (3) | 0.0053 (19) | 0.013 (2) | 0.009 (2) |
C13 | 0.070 (3) | 0.094 (3) | 0.064 (4) | −0.015 (3) | 0.008 (3) | −0.001 (3) |
C14 | 0.071 (3) | 0.137 (6) | 0.100 (6) | 0.013 (3) | 0.024 (4) | −0.013 (4) |
C15 | 0.074 (2) | 0.048 (2) | 0.039 (2) | 0.010 (2) | −0.003 (2) | −0.002 (2) |
C16 | 0.219 (8) | 0.052 (3) | 0.054 (3) | −0.018 (4) | −0.018 (4) | −0.003 (2) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.134 (2) | C13—C14 | 1.497 (8) |
Sn1—C7 | 2.127 (2) | C15—C16 | 1.531 (6) |
Sn1—C13 | 2.128 (5) | C2—H2 | 0.93 |
Sn1—O1 | 2.171 (3) | C3—H3 | 0.93 |
Sn1—O2i | 2.522 (3) | C4—H4 | 0.93 |
Cl1—C16 | 1.729 (5) | C5—H5 | 0.93 |
O1—C15 | 1.264 (5) | C6—H6 | 0.93 |
O2—C15 | 1.234 (5) | C8—H8 | 0.93 |
C1—C2 | 1.39 | C9—H9 | 0.93 |
C1—C6 | 1.39 | C10—H10 | 0.93 |
C2—C3 | 1.39 | C11—H11 | 0.93 |
C3—C4 | 1.39 | C12—H12 | 0.93 |
C4—C5 | 1.39 | C13—H13a | 0.97 |
C5—C6 | 1.39 | C13—H13b | 0.97 |
C7—C8 | 1.39 | C14—H14a | 0.96 |
C7—C12 | 1.39 | C14—H14b | 0.96 |
C8—C9 | 1.39 | C14—H14c | 0.96 |
C9—C10 | 1.39 | C16—H16a | 0.97 |
C10—C11 | 1.39 | C16—H16b | 0.97 |
C11—C12 | 1.39 | | |
| | | |
C1—Sn1—C7 | 115.2 (1) | C2—C3—H3 | 120.0 |
C1—Sn1—C13 | 117.3 (2) | C4—C3—H3 | 120.0 |
C1—Sn1—O1 | 89.9 (1) | C5—C4—H4 | 120.0 |
C1—Sn1—O2i | 83.6 (1) | C3—C4—H4 | 120.0 |
C7—Sn1—C13 | 124.5 (2) | C6—C5—H5 | 120.0 |
C7—Sn1—O1 | 94.4 (1) | C4—C5—H5 | 120.0 |
C7—Sn1—O2i | 85.2 (1) | C5—C6—H6 | 120.0 |
C13—Sn1—O1 | 102.2 (2) | C1—C6—H6 | 120.0 |
C13—Sn1—O2i | 84.0 (2) | C9—C8—H8 | 120.0 |
O1—Sn1—O2i | 172.6 (1) | C7—C8—H8 | 120.0 |
C15—O1—Sn1 | 125.1 (3) | C8—C9—H9 | 120.0 |
C15—O2—Sn1ii | 139.2 (3) | C10—C9—H9 | 120.0 |
C2—C1—C6 | 120.0 | C11—C10—H10 | 120.0 |
C2—C1—Sn1 | 120.0 (2) | C9—C10—H10 | 120.0 |
C6—C1—Sn1 | 120.0 (2) | C12—C11—H11 | 120.0 |
C3—C2—C1 | 120.0 | C10—C11—H11 | 120.0 |
C2—C3—C4 | 120.0 | C11—C12—H12 | 120.0 |
C5—C4—C3 | 120.0 | C7—C12—H12 | 120.0 |
C6—C5—C4 | 120.0 | C14—C13—H13a | 108.1 |
C5—C6—C1 | 120.0 | Sn1—C13—H13a | 108.1 |
C8—C7—C12 | 120.0 | C14—C13—H13b | 108.1 |
C8—C7—Sn1 | 121.7 (2) | Sn1—C13—H13b | 108.1 |
C12—C7—Sn1 | 118.2 (1) | H13a—C13—H13b | 107.3 |
C9—C8—C7 | 120.0 | C13—C14—H14a | 109.5 |
C8—C9—C10 | 120.0 | C13—C14—H14b | 109.5 |
C11—C10—C9 | 120.0 | H14a—C14—H14b | 109.5 |
C12—C11—C10 | 120.0 | C13—C14—H14c | 109.5 |
C11—C12—C7 | 120.0 | H14a—C14—H14c | 109.5 |
C14—C13—Sn1 | 117.0 (5) | H14b—C14—H14c | 109.5 |
O2—C15—O1 | 125.5 (4) | C15—C16—H16a | 108.1 |
O2—C15—C16 | 117.3 (4) | Cl1—C16—H16a | 108.1 |
O1—C15—C16 | 117.2 (4) | C15—C16—H16b | 108.1 |
C15—C16—Cl1 | 116.6 (4) | Cl1—C16—H16b | 108.1 |
C3—C2—H2 | 120.0 | H16a—C16—H16b | 107.3 |
C1—C2—H2 | 120.0 | | |
| | | |
C7—Sn1—O1—C15 | 65.5 (4) | C13—Sn1—C7—C12 | −144.3 (2) |
C13—Sn1—O1—C15 | −61.3 (4) | C1—Sn1—C7—C12 | 15.6 (2) |
C1—Sn1—O1—C15 | −179.2 (4) | O1—Sn1—C7—C12 | 107.5 (2) |
C7—Sn1—C1—C2 | −139.6 (2) | O2i—Sn1—C7—C12 | −65.0 (2) |
C13—Sn1—C1—C2 | 21.8 (3) | C12—C7—C8—C9 | 0.0 |
O1—Sn1—C1—C2 | 125.6 (2) | Sn1—C7—C8—C9 | −175.8 (2) |
O2i—Sn1—C1—C2 | −58.0 (2) | C7—C8—C9—C10 | 0.0 |
C7—Sn1—C1—C6 | 39.1 (2) | C8—C9—C10—C11 | 0.0 |
C13—Sn1—C1—C6 | −159.4 (2) | C9—C10—C11—C12 | 0.0 |
O1—Sn1—C1—C6 | −55.7 (2) | C10—C11—C12—C7 | 0.0 |
O2i—Sn1—C1—C6 | 120.8 (2) | C8—C7—C12—C11 | 0.0 |
C6—C1—C2—C3 | 0.0 | Sn1—C7—C12—C11 | 175.9 (2) |
Sn1—C1—C2—C3 | 178.7 (2) | C7—Sn1—C13—C14 | −130.3 (5) |
C1—C2—C3—C4 | 0.0 | C1—Sn1—C13—C14 | 70.1 (6) |
C2—C3—C4—C5 | 0.0 | O1—Sn1—C13—C14 | −26.1 (6) |
C3—C4—C5—C6 | 0.0 | O2i—Sn1—C13—C14 | 149.7 (5) |
C4—C5—C6—C1 | 0.0 | Sn1ii—O2—C15—O1 | −175.6 (3) |
C2—C1—C6—C5 | 0.0 | Sn1ii—O2—C15—C16 | 3.9 (7) |
Sn1—C1—C6—C5 | −178.7 (2) | Sn1—O1—C15—O2 | 13.7 (7) |
C13—Sn1—C7—C8 | 31.5 (2) | Sn1—O1—C15—C16 | −165.8 (4) |
C1—Sn1—C7—C8 | −168.6 (2) | O2—C15—C16—Cl1 | 177.1 (5) |
O1—Sn1—C7—C8 | −76.6 (2) | O1—C15—C16—Cl1 | −3.4 (8) |
O2i—Sn1—C7—C8 | 110.8 (2) | | |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2. |