Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034672/xu2117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034672/xu2117Isup2.hkl |
CCDC reference: 625038
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.017
- wR factor = 0.059
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2650 Count of symmetry unique reflns 1945 Completeness (_total/calc) 136.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 705 Fraction of Friedel pairs measured 0.362 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: initial atomic coordinates were taken from the structure of the monochloroacetate analog (Amini et al., 2006); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
[Sn(C2HCl2O2)(C2H5)(C6H5)2] | F(000) = 848 |
Mr = 429.88 | Dx = 1.691 Mg m−3 |
Monoclinic, Cc | Melting point = 418–419 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.5470 (6) Å | Cell parameters from 5205 reflections |
b = 12.0008 (5) Å | θ = 2.5–29.8° |
c = 11.2363 (4) Å | µ = 1.83 mm−1 |
β = 93.452 (1)° | T = 173 K |
V = 1688.83 (12) Å3 | Block, colorless |
Z = 4 | 0.36 × 0.18 × 0.10 mm |
Bruker APEX-II CCD area-detector diffractometer | 2650 independent reflections |
Radiation source: fine-focus sealed tube | 2625 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
φ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.648, Tmax = 0.838 | k = −15→15 |
4353 measured reflections | l = −7→14 |
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)] = 0.017 | H-atom parameters constrained |
wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0414P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max = 0.001 |
2650 reflections | Δρmax = 0.56 e Å−3 |
188 parameters | Δρmin = −0.81 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 743 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (2) |
Experimental. 1H NMR (in CDCl3, δ): CH3 (1.46–1.51, triplet), CH2 (1.81–1.89, quartet), C6H5 (7.47–7.77, multiplet) and CHCl2 (6.01). 13C NMR (in CDCl3, δ): 9.6, 9.7, 128.3, 129.1, 130.5, 135.5, 136.5, and 137.9. 119Sn NMR (in CDCl3, δ): 11. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.50000 (1) | 0.5491 (1) | 0.5000 (1) | 0.01537 (7) | |
Cl1 | 0.63719 (8) | 0.83252 (7) | 0.76804 (9) | 0.02974 (19) | |
Cl2 | 0.4768 (1) | 0.78285 (9) | 0.9351 (1) | 0.0469 (3) | |
O1 | 0.5139 (2) | 0.6584 (2) | 0.6575 (2) | 0.0193 (4) | |
O2 | 0.4973 (2) | 0.5468 (2) | 0.8140 (3) | 0.0201 (6) | |
C1 | 0.5031 (3) | 0.6958 (3) | 0.3945 (3) | 0.0169 (6) | |
C2 | 0.4234 (2) | 0.7143 (3) | 0.3054 (3) | 0.0203 (6) | |
C3 | 0.4227 (3) | 0.8114 (3) | 0.2367 (3) | 0.0259 (7) | |
C4 | 0.5032 (3) | 0.8884 (3) | 0.2546 (3) | 0.0281 (8) | |
C5 | 0.5839 (3) | 0.8712 (3) | 0.3432 (4) | 0.0284 (8) | |
C6 | 0.5831 (3) | 0.7749 (3) | 0.4135 (3) | 0.0220 (6) | |
C7 | 0.6505 (3) | 0.4764 (3) | 0.5462 (3) | 0.0167 (6) | |
C8 | 0.6645 (3) | 0.4000 (3) | 0.6397 (3) | 0.0206 (6) | |
C9 | 0.7644 (3) | 0.3516 (3) | 0.6661 (3) | 0.0259 (7) | |
C10 | 0.8496 (3) | 0.3788 (3) | 0.5993 (3) | 0.0258 (7) | |
C11 | 0.8367 (3) | 0.4545 (3) | 0.5063 (4) | 0.0243 (8) | |
C12 | 0.7376 (3) | 0.5031 (3) | 0.4805 (3) | 0.0201 (6) | |
C13 | 0.3492 (3) | 0.4753 (3) | 0.5280 (4) | 0.0243 (7) | |
C14 | 0.2719 (3) | 0.5498 (3) | 0.5892 (5) | 0.034 (1) | |
C15 | 0.5245 (2) | 0.6352 (2) | 0.7665 (3) | 0.0168 (6) | |
C16 | 0.5757 (3) | 0.7258 (3) | 0.8480 (3) | 0.0235 (7) | |
H2 | 0.3688 | 0.6603 | 0.2910 | 0.024* | |
H3 | 0.3665 | 0.8241 | 0.1777 | 0.031* | |
H4 | 0.5037 | 0.9534 | 0.2064 | 0.034* | |
H5 | 0.6393 | 0.9246 | 0.3559 | 0.034* | |
H6 | 0.6376 | 0.7636 | 0.4747 | 0.026* | |
H8 | 0.6059 | 0.3810 | 0.6855 | 0.025* | |
H9 | 0.7738 | 0.2999 | 0.7299 | 0.031* | |
H10 | 0.9174 | 0.3455 | 0.6172 | 0.031* | |
H11 | 0.8954 | 0.4730 | 0.4605 | 0.029* | |
H12 | 0.7291 | 0.5553 | 0.4171 | 0.024* | |
H13a | 0.3157 | 0.4523 | 0.4499 | 0.029* | |
H13b | 0.3612 | 0.4071 | 0.5766 | 0.029* | |
H14a | 0.2048 | 0.5096 | 0.5982 | 0.051* | |
H14b | 0.2578 | 0.6169 | 0.5411 | 0.051* | |
H14c | 0.3030 | 0.5711 | 0.6681 | 0.051* | |
H16 | 0.6313 | 0.6899 | 0.9028 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0176 (1) | 0.0164 (1) | 0.0121 (1) | 0.0011 (1) | 0.0003 (1) | 0.0011 (1) |
Cl1 | 0.0316 (4) | 0.0223 (4) | 0.0349 (5) | −0.0059 (3) | −0.0015 (4) | 0.0027 (3) |
Cl2 | 0.0753 (8) | 0.0293 (5) | 0.0395 (6) | −0.0063 (5) | 0.0304 (6) | −0.0154 (4) |
O1 | 0.030 (1) | 0.017 (1) | 0.011 (1) | 0.004 (1) | 0.000 (1) | 0.000 (1) |
O2 | 0.028 (1) | 0.018 (1) | 0.014 (1) | 0.000 (1) | 0.000 (1) | 0.002 (1) |
C1 | 0.020 (1) | 0.018 (2) | 0.012 (2) | 0.005 (12) | 0.002 (1) | 0.001 (1) |
C2 | 0.020 (1) | 0.023 (2) | 0.018 (2) | 0.000 (1) | 0.000 (1) | 0.001 (1) |
C3 | 0.028 (2) | 0.030 (2) | 0.019 (2) | 0.010 (2) | −0.002 (1) | 0.003 (1) |
C4 | 0.037 (2) | 0.024 (2) | 0.024 (2) | 0.004 (1) | 0.004 (2) | 0.007 (1) |
C5 | 0.032 (2) | 0.023 (2) | 0.031 (2) | −0.004 (1) | 0.003 (2) | 0.008 (2) |
C6 | 0.024 (2) | 0.025 (2) | 0.017 (2) | 0.003 (1) | −0.001 (1) | 0.003 (1) |
C7 | 0.021 (2) | 0.014 (1) | 0.015 (2) | 0.001 (1) | −0.001 (1) | −0.003 (1) |
C8 | 0.027 (2) | 0.019 (1) | 0.016 (2) | 0.001 (1) | 0.003 (1) | 0.001 (1) |
C9 | 0.034 (2) | 0.021 (2) | 0.022 (2) | 0.006 (1) | −0.002 (1) | 0.004 (1) |
C10 | 0.023 (2) | 0.025 (2) | 0.029 (2) | 0.006 (1) | −0.005 (1) | −0.004 (1) |
C11 | 0.020 (2) | 0.024 (2) | 0.030 (2) | −0.001 (1) | 0.005 (2) | −0.004 (1) |
C12 | 0.026 (2) | 0.015 (2) | 0.020 (2) | −0.002 (1) | 0.000 (1) | 0.001 (1) |
C13 | 0.024 (2) | 0.026 (2) | 0.023 (2) | −0.001 (1) | 0.004 (2) | −0.002 (2) |
C14 | 0.022 (2) | 0.038 (2) | 0.041 (3) | 0.001 (1) | 0.010 (2) | −0.005 (2) |
C15 | 0.019 (1) | 0.017 (1) | 0.014 (2) | 0.006 (1) | 0.001 (1) | 0.000 (1) |
C16 | 0.034 (2) | 0.016 (1) | 0.020 (2) | 0.001 (1) | −0.005 (1) | 0.001 (1) |
Sn1—C1 | 2.124 (3) | C11—C12 | 1.388 (5) |
Sn1—C7 | 2.116 (3) | C13—C14 | 1.514 (6) |
Sn1—C13 | 2.129 (4) | C15—C16 | 1.537 (4) |
Sn1—O1 | 2.201 (2) | C2—H2 | 0.95 |
Sn1—O2i | 2.384 (3) | C3—H3 | 0.95 |
Cl1—C16 | 1.769 (4) | C4—H4 | 0.95 |
Cl2—C16 | 1.764 (4) | C5—H5 | 0.95 |
O1—C15 | 1.255 (4) | C6—H6 | 0.95 |
O2—C15 | 1.244 (4) | C8—H8 | 0.95 |
C1—C2 | 1.389 (4) | C9—H9 | 0.95 |
C1—C6 | 1.389 (5) | C10—H10 | 0.95 |
C2—C3 | 1.397 (5) | C11—H11 | 0.95 |
C3—C4 | 1.375 (5) | C12—H12 | 0.95 |
C4—C5 | 1.392 (5) | C13—H13a | 0.99 |
C5—C6 | 1.401 (5) | C13—H13b | 0.99 |
C7—C12 | 1.393 (5) | C14—H14a | 0.98 |
C7—C8 | 1.397 (5) | C14—H14b | 0.98 |
C8—C9 | 1.398 (5) | C14—H14c | 0.98 |
C9—C10 | 1.382 (5) | C16—H16 | 1.00 |
C10—C11 | 1.386 (6) | ||
C1—Sn1—C7 | 115.6 (1) | C1—C2—H2 | 119.6 |
C1—Sn1—C13 | 118.2 (1) | C3—C2—H2 | 119.6 |
C1—Sn1—O1 | 87.2 (1) | C4—C3—H3 | 120.0 |
C1—Sn1—O2i | 84.9 (1) | C2—C3—H3 | 120.0 |
C7—Sn1—C13 | 125.5 (1) | C3—C4—H4 | 120.0 |
C7—Sn1—O1 | 91.3 (1) | C5—C4—H4 | 120.0 |
C7—Sn1—O2i | 88.9 (1) | C4—C5—H5 | 120.1 |
C13—Sn1—O1 | 99.0 (1) | C6—C5—H5 | 120.1 |
C13—Sn1—O2i | 87.9 (1) | C1—C6—H6 | 119.8 |
O1—Sn1—O2i | 171.3 (1) | C5—C6—H6 | 119.8 |
C15—O1—Sn1 | 130.6 (2) | C7—C8—H8 | 119.9 |
C15—O2—Sn1ii | 142.9 (2) | C9—C8—H8 | 119.9 |
C2—C1—C6 | 118.9 (3) | C10—C9—H9 | 120.0 |
C2—C1—Sn1 | 119.9 (2) | C8—C9—H9 | 120.0 |
C6—C1—Sn1 | 121.2 (2) | C9—C10—H10 | 119.8 |
C1—C2—C3 | 120.8 (3) | C11—C10—H10 | 119.8 |
C4—C3—C2 | 120.0 (3) | C10—C11—H11 | 120.2 |
C3—C4—C5 | 120.1 (3) | C12—C11—H11 | 120.2 |
C4—C5—C6 | 119.7 (3) | C11—C12—H12 | 119.5 |
C1—C6—C5 | 120.5 (3) | C7—C12—H12 | 119.5 |
C12—C7—C8 | 118.8 (3) | C14—C13—H13a | 108.5 |
C12—C7—Sn1 | 119.5 (3) | Sn1—C13—H13a | 108.5 |
C8—C7—Sn1 | 121.7 (3) | C14—C13—H13b | 108.5 |
C7—C8—C9 | 120.2 (3) | Sn1—C13—H13b | 108.5 |
C10—C9—C8 | 120.0 (3) | H13a—C13—H13b | 107.5 |
C9—C10—C11 | 120.3 (3) | C13—C14—H14a | 109.5 |
C10—C11—C12 | 119.7 (4) | C13—C14—H14b | 109.5 |
C11—C12—C7 | 120.9 (3) | H14a—C14—H14b | 109.5 |
C14—C13—Sn1 | 114.9 (3) | C13—C14—H14c | 109.5 |
O2—C15—O1 | 126.3 (3) | H14a—C14—H14c | 109.5 |
O2—C15—C16 | 117.5 (3) | H14b—C14—H14c | 109.5 |
O1—C15—C16 | 116.2 (3) | C15—C16—H16 | 108.3 |
C15—C16—Cl2 | 108.8 (2) | Cl2—C16—H16 | 108.3 |
C15—C16—Cl1 | 112.9 (3) | Cl1—C16—H16 | 108.3 |
Cl2—C16—Cl1 | 110.1 (2) | ||
C7—Sn1—O1—C15 | −59.5 (3) | C13—Sn1—C7—C8 | −27.4 (3) |
C1—Sn1—O1—C15 | −175.1 (3) | O1—Sn1—C7—C8 | 74.6 (3) |
C13—Sn1—O1—C15 | 66.7 (3) | O2i—Sn1—C7—C8 | −114.1 (3) |
C7—Sn1—C1—C2 | 142.5 (3) | C12—C7—C8—C9 | −0.1 (5) |
C13—Sn1—C1—C2 | −28.7 (3) | Sn1—C7—C8—C9 | 178.5 (3) |
O1—Sn1—C1—C2 | −127.5 (3) | C7—C8—C9—C10 | −0.3 (5) |
O2i—Sn1—C1—C2 | 56.1 (3) | C8—C9—C10—C11 | 0.3 (5) |
C7—Sn1—C1—C6 | −38.2 (3) | C9—C10—C11—C12 | 0.0 (6) |
C13—Sn1—C1—C6 | 150.6 (3) | C10—C11—C12—C7 | −0.4 (5) |
O1—Sn1—C1—C6 | 51.8 (3) | C8—C7—C12—C11 | 0.5 (5) |
O2i—Sn1—C1—C6 | −124.6 (3) | Sn1—C7—C12—C11 | −178.2 (3) |
C6—C1—C2—C3 | −0.7 (5) | C7—Sn1—C13—C14 | 129.9 (3) |
Sn1—C1—C2—C3 | 178.6 (2) | C1—Sn1—C13—C14 | −59.8 (4) |
C1—C2—C3—C4 | 1.9 (5) | O1—Sn1—C13—C14 | 31.9 (4) |
C2—C3—C4—C5 | −1.7 (6) | O2i—Sn1—C13—C14 | −142.9 (4) |
C3—C4—C5—C6 | 0.4 (6) | Sn1ii—O2—C15—O1 | 176.6 (3) |
C2—C1—C6—C5 | −0.6 (5) | Sn1ii—O2—C15—C16 | −3.7 (5) |
Sn1—C1—C6—C5 | −180.0 (3) | Sn1—O1—C15—O2 | −24.0 (5) |
C4—C5—C6—C1 | 0.8 (6) | Sn1—O1—C15—C16 | 156.3 (2) |
C1—Sn1—C7—C12 | −19.3 (3) | O2—C15—C16—Cl2 | −70.8 (3) |
C13—Sn1—C7—C12 | 151.2 (3) | O1—C15—C16—Cl2 | 109.0 (3) |
O1—Sn1—C7—C12 | −106.8 (3) | O2—C15—C16—Cl1 | 166.7 (2) |
O2i—Sn1—C7—C12 | 64.5 (3) | O1—C15—C16—Cl1 | −13.6 (4) |
C1—Sn1—C7—C8 | 162.1 (3) |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2. |
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