metal-organic compounds
The structure of the title compound, [Sn(CH3)3(C8H8NO4)], is composed of two independent monomers in the asymmetric unit, which form polymeric chains involving both O atoms of the acid moieties lying parallel to the b axis, and are separated by one half unit cell along the a axis. The geometry around the Sn atoms in both monomers is distorted trigonal-bipyramidal, where three methyl C atoms occupy the equatorial positions with almost identical Sn-C distances, and O atoms from two symmetry-related ligands are in the axial positions with significantly different Sn-O distances.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007974/ac6093sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007974/ac6093Isup2.hkl |
CCDC reference: 239048
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.006 Å
- R factor = 0.039
- wR factor = 0.081
- Data-to-parameter ratio = 20.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O8 .. C10 .. 2.97 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C11 H17 N1 O4 Sn1 Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion
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.
Trimethyltin(IV)2-(N-maleoyl)-2-methylpropionate top
Crystal data top
[Sn(C8H8NO4)(CH3)3] | F(000) = 1376 |
Mr = 345.95 | Dx = 1.660 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11788 reflections |
a = 21.738 (5) Å | θ = 3.4–27.5° |
b = 9.700 (2) Å | µ = 1.85 mm−1 |
c = 13.447 (3) Å | T = 173 K |
β = 102.442 (13)° | Block, colorless |
V = 2768.8 (11) Å3 | 0.18 × 0.15 × 0.15 mm |
Z = 8 |
Data collection top
Nonius KappaCCD diffractometer | 6332 independent reflections |
Radiation source: fine-focus sealed tube | 4188 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω and φ scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −28→28 |
Tmin = 0.725, Tmax = 0.761 | k = −12→12 |
11788 measured reflections | l = −17→17 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.026P)2] where P = (Fo2 + 2Fc2)/3 |
6332 reflections | (Δ/σ)max = 0.001 |
307 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −0.81 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.477587 (11) | 1.09138 (3) | 0.20148 (2) | 0.02330 (9) | |
O1 | 0.40017 (11) | 0.9629 (3) | 0.1353 (2) | 0.0267 (7) | |
O2 | 0.44006 (11) | 0.7749 (3) | 0.2216 (2) | 0.0327 (7) | |
O3 | 0.31989 (13) | 0.9251 (3) | 0.2794 (2) | 0.0391 (8) | |
O4 | 0.20732 (13) | 0.7736 (3) | −0.0259 (3) | 0.0581 (10) | |
N1 | 0.28187 (14) | 0.8425 (3) | 0.1165 (3) | 0.0270 (8) | |
C1 | 0.46890 (18) | 1.0801 (4) | 0.3552 (3) | 0.0293 (10) | |
H1A | 0.5100 | 1.0589 | 0.3989 | 0.044* | |
H1B | 0.4388 | 1.0075 | 0.3623 | 0.044* | |
H1C | 0.4538 | 1.1688 | 0.3756 | 0.044* | |
C2 | 0.54781 (17) | 0.9871 (4) | 0.1436 (3) | 0.0344 (11) | |
H2A | 0.5278 | 0.9291 | 0.0860 | 0.052* | |
H2B | 0.5728 | 0.9293 | 0.1971 | 0.052* | |
H2C | 0.5753 | 1.0547 | 0.1208 | 0.052* | |
C3 | 0.43501 (17) | 1.2571 (4) | 0.1090 (3) | 0.0347 (11) | |
H3A | 0.4178 | 1.2234 | 0.0399 | 0.052* | |
H3B | 0.4666 | 1.3284 | 0.1067 | 0.052* | |
H3C | 0.4010 | 1.2960 | 0.1376 | 0.052* | |
C4 | 0.39788 (17) | 0.8360 (4) | 0.1629 (3) | 0.0247 (9) | |
C5 | 0.33779 (17) | 0.7603 (4) | 0.1066 (3) | 0.0280 (10) | |
C6 | 0.33220 (19) | 0.6169 (4) | 0.1509 (4) | 0.0482 (14) | |
H6A | 0.3278 | 0.6256 | 0.2216 | 0.072* | |
H6B | 0.3701 | 0.5633 | 0.1487 | 0.072* | |
H6C | 0.2951 | 0.5700 | 0.1108 | 0.072* | |
C7 | 0.3432 (2) | 0.7531 (5) | −0.0049 (3) | 0.0512 (14) | |
H7A | 0.3386 | 0.8458 | −0.0345 | 0.077* | |
H7B | 0.3099 | 0.6933 | −0.0428 | 0.077* | |
H7C | 0.3845 | 0.7155 | −0.0088 | 0.077* | |
C8 | 0.27819 (18) | 0.9166 (4) | 0.2049 (3) | 0.0305 (10) | |
C9 | 0.21281 (18) | 0.9710 (4) | 0.1881 (4) | 0.0376 (11) | |
H9 | 0.1969 | 1.0288 | 0.2337 | 0.045* | |
C10 | 0.18064 (19) | 0.9258 (4) | 0.0997 (4) | 0.0394 (12) | |
H10 | 0.1378 | 0.9465 | 0.0711 | 0.047* | |
C11 | 0.2216 (2) | 0.8384 (5) | 0.0524 (4) | 0.0378 (12) | |
Sn2 | 0.030662 (11) | 0.08059 (3) | 0.27622 (2) | 0.02180 (9) | |
O5 | 0.10630 (11) | 0.2101 (3) | 0.2496 (2) | 0.0275 (7) | |
O6 | 0.04816 (11) | 0.3988 (2) | 0.2055 (2) | 0.0268 (7) | |
O7 | 0.28836 (12) | 0.2866 (3) | 0.1911 (2) | 0.0393 (8) | |
O8 | 0.16758 (12) | 0.3893 (3) | 0.4203 (2) | 0.0379 (8) | |
N2 | 0.21347 (13) | 0.3533 (3) | 0.2827 (2) | 0.0221 (7) | |
C12 | 0.00419 (17) | 0.1993 (4) | 0.3936 (3) | 0.0277 (10) | |
H12A | 0.0395 | 0.2581 | 0.4260 | 0.042* | |
H12B | −0.0069 | 0.1373 | 0.4446 | 0.042* | |
H12C | −0.0322 | 0.2570 | 0.3642 | 0.042* | |
C13 | 0.09606 (17) | −0.0753 (4) | 0.3378 (3) | 0.0338 (11) | |
H13A | 0.1361 | −0.0327 | 0.3711 | 0.051* | |
H13B | 0.1029 | −0.1360 | 0.2829 | 0.051* | |
H13C | 0.0794 | −0.1292 | 0.3877 | 0.051* | |
C14 | −0.01900 (18) | 0.0834 (4) | 0.1226 (3) | 0.0305 (10) | |
H14A | −0.0410 | 0.1717 | 0.1078 | 0.046* | |
H14B | −0.0498 | 0.0080 | 0.1110 | 0.046* | |
H14C | 0.0107 | 0.0717 | 0.0778 | 0.046* | |
C15 | 0.09923 (17) | 0.3367 (4) | 0.2247 (3) | 0.0212 (9) | |
C16 | 0.15965 (16) | 0.4097 (4) | 0.2076 (3) | 0.0214 (9) | |
C17 | 0.15709 (17) | 0.5653 (4) | 0.2204 (3) | 0.0316 (10) | |
H17A | 0.1976 | 0.6057 | 0.2151 | 0.047* | |
H17B | 0.1485 | 0.5868 | 0.2873 | 0.047* | |
H17C | 0.1235 | 0.6036 | 0.1670 | 0.047* | |
C18 | 0.16304 (17) | 0.3731 (4) | 0.0976 (3) | 0.0300 (10) | |
H18A | 0.1681 | 0.2732 | 0.0918 | 0.045* | |
H18B | 0.1991 | 0.4203 | 0.0798 | 0.045* | |
H18C | 0.1241 | 0.4026 | 0.0510 | 0.045* | |
C19 | 0.27049 (17) | 0.2961 (4) | 0.2692 (3) | 0.0281 (10) | |
C20 | 0.30426 (19) | 0.2533 (5) | 0.3726 (3) | 0.0420 (12) | |
H20 | 0.3443 | 0.2095 | 0.3878 | 0.050* | |
C21 | 0.27103 (18) | 0.2844 (5) | 0.4397 (3) | 0.0410 (12) | |
H21 | 0.2830 | 0.2683 | 0.5109 | 0.049* | |
C22 | 0.21117 (19) | 0.3495 (4) | 0.3854 (3) | 0.0302 (10) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02313 (15) | 0.02085 (16) | 0.02611 (18) | −0.00095 (12) | 0.00574 (12) | 0.00049 (13) |
O1 | 0.0269 (14) | 0.0233 (15) | 0.0279 (17) | −0.0063 (12) | 0.0017 (12) | 0.0011 (13) |
O2 | 0.0240 (14) | 0.0279 (16) | 0.043 (2) | 0.0037 (13) | 0.0002 (13) | 0.0005 (14) |
O3 | 0.0357 (16) | 0.057 (2) | 0.0230 (18) | 0.0037 (16) | 0.0040 (14) | −0.0005 (16) |
O4 | 0.0416 (19) | 0.065 (2) | 0.056 (3) | −0.0039 (18) | −0.0152 (17) | −0.022 (2) |
N1 | 0.0197 (16) | 0.0294 (19) | 0.030 (2) | −0.0026 (15) | 0.0024 (15) | −0.0010 (17) |
C1 | 0.035 (2) | 0.028 (2) | 0.027 (2) | 0.000 (2) | 0.0106 (19) | −0.002 (2) |
C2 | 0.032 (2) | 0.034 (3) | 0.041 (3) | −0.001 (2) | 0.014 (2) | −0.003 (2) |
C3 | 0.036 (2) | 0.029 (2) | 0.036 (3) | 0.000 (2) | −0.001 (2) | 0.003 (2) |
C4 | 0.025 (2) | 0.020 (2) | 0.031 (3) | −0.0030 (19) | 0.0102 (19) | −0.0071 (19) |
C5 | 0.025 (2) | 0.026 (2) | 0.033 (3) | −0.0051 (19) | 0.0040 (18) | −0.003 (2) |
C6 | 0.031 (2) | 0.024 (2) | 0.085 (4) | −0.005 (2) | 0.002 (3) | 0.003 (2) |
C7 | 0.047 (3) | 0.064 (3) | 0.044 (3) | −0.006 (3) | 0.012 (2) | −0.025 (3) |
C8 | 0.032 (2) | 0.029 (2) | 0.034 (3) | 0.001 (2) | 0.013 (2) | 0.007 (2) |
C9 | 0.032 (2) | 0.035 (3) | 0.051 (3) | 0.005 (2) | 0.019 (2) | 0.009 (2) |
C10 | 0.027 (2) | 0.039 (3) | 0.051 (3) | 0.005 (2) | 0.006 (2) | 0.010 (3) |
C11 | 0.038 (3) | 0.033 (3) | 0.038 (3) | −0.010 (2) | −0.002 (2) | 0.008 (2) |
Sn2 | 0.02237 (14) | 0.01878 (15) | 0.02483 (17) | −0.00005 (12) | 0.00639 (12) | 0.00005 (12) |
O5 | 0.0239 (14) | 0.0179 (15) | 0.0431 (19) | 0.0002 (12) | 0.0125 (13) | 0.0054 (13) |
O6 | 0.0244 (14) | 0.0238 (16) | 0.0333 (18) | 0.0010 (13) | 0.0088 (12) | 0.0001 (13) |
O7 | 0.0306 (15) | 0.059 (2) | 0.0315 (19) | 0.0086 (15) | 0.0131 (14) | −0.0022 (16) |
O8 | 0.0377 (16) | 0.051 (2) | 0.0276 (18) | 0.0110 (15) | 0.0128 (14) | −0.0049 (15) |
N2 | 0.0203 (16) | 0.0252 (18) | 0.021 (2) | 0.0020 (15) | 0.0040 (14) | 0.0014 (15) |
C12 | 0.035 (2) | 0.021 (2) | 0.028 (3) | −0.0046 (19) | 0.0093 (19) | −0.0053 (18) |
C13 | 0.028 (2) | 0.029 (2) | 0.043 (3) | −0.001 (2) | 0.004 (2) | 0.007 (2) |
C14 | 0.037 (2) | 0.032 (2) | 0.021 (2) | −0.006 (2) | 0.0042 (19) | 0.003 (2) |
C15 | 0.022 (2) | 0.023 (2) | 0.019 (2) | −0.0024 (18) | 0.0053 (17) | −0.0041 (18) |
C16 | 0.0206 (19) | 0.022 (2) | 0.021 (2) | 0.0015 (18) | 0.0037 (16) | 0.0036 (18) |
C17 | 0.028 (2) | 0.022 (2) | 0.045 (3) | −0.0033 (19) | 0.008 (2) | 0.004 (2) |
C18 | 0.023 (2) | 0.043 (3) | 0.025 (3) | −0.0008 (19) | 0.0065 (18) | 0.006 (2) |
C19 | 0.0208 (19) | 0.035 (3) | 0.030 (3) | −0.0003 (19) | 0.0084 (18) | −0.001 (2) |
C20 | 0.026 (2) | 0.060 (3) | 0.037 (3) | 0.009 (2) | 0.000 (2) | 0.008 (3) |
C21 | 0.032 (2) | 0.064 (3) | 0.023 (3) | 0.008 (2) | −0.002 (2) | 0.006 (2) |
C22 | 0.030 (2) | 0.033 (2) | 0.029 (3) | 0.001 (2) | 0.009 (2) | 0.001 (2) |
Geometric parameters (Å, º) top
Sn1—C2 | 2.114 (4) | Sn2—C14 | 2.115 (4) |
Sn1—C3 | 2.119 (4) | Sn2—C13 | 2.118 (4) |
Sn1—C1 | 2.119 (4) | Sn2—C12 | 2.131 (4) |
Sn1—O1 | 2.129 (2) | Sn2—O5 | 2.159 (2) |
Sn1—O2i | 2.578 (3) | Sn2—O6iii | 2.508 (3) |
O1—C4 | 1.290 (4) | O5—C15 | 1.273 (4) |
O2—C4 | 1.226 (4) | O6—C15 | 1.240 (4) |
O2—Sn1ii | 2.578 (3) | O6—Sn2iv | 2.508 (3) |
O3—C8 | 1.201 (4) | O7—C19 | 1.199 (5) |
O4—C11 | 1.208 (5) | O8—C22 | 1.208 (5) |
N1—C8 | 1.405 (5) | N2—C22 | 1.394 (5) |
N1—C11 | 1.405 (5) | N2—C19 | 1.405 (5) |
N1—C5 | 1.483 (5) | N2—C16 | 1.476 (4) |
C1—H1A | 0.9800 | C12—H12A | 0.9800 |
C1—H1B | 0.9800 | C12—H12B | 0.9800 |
C1—H1C | 0.9800 | C12—H12C | 0.9800 |
C2—H2A | 0.9800 | C13—H13A | 0.9800 |
C2—H2B | 0.9800 | C13—H13B | 0.9800 |
C2—H2C | 0.9800 | C13—H13C | 0.9800 |
C3—H3A | 0.9800 | C14—H14A | 0.9800 |
C3—H3B | 0.9800 | C14—H14B | 0.9800 |
C3—H3C | 0.9800 | C14—H14C | 0.9800 |
C4—C5 | 1.547 (5) | C15—C16 | 1.552 (5) |
C5—C6 | 1.528 (5) | C16—C17 | 1.522 (5) |
C5—C7 | 1.530 (6) | C16—C18 | 1.539 (5) |
C6—H6A | 0.9800 | C17—H17A | 0.9800 |
C6—H6B | 0.9800 | C17—H17B | 0.9800 |
C6—H6C | 0.9800 | C17—H17C | 0.9800 |
C7—H7A | 0.9800 | C18—H18A | 0.9800 |
C7—H7B | 0.9800 | C18—H18B | 0.9800 |
C7—H7C | 0.9800 | C18—H18C | 0.9800 |
C8—C9 | 1.487 (5) | C19—C20 | 1.485 (5) |
C9—C10 | 1.318 (6) | C20—C21 | 1.307 (6) |
C9—H9 | 0.9500 | C20—H20 | 0.9500 |
C10—C11 | 1.470 (6) | C21—C22 | 1.488 (5) |
C10—H10 | 0.9500 | C21—H21 | 0.9500 |
C2—Sn1—C3 | 113.90 (17) | C14—Sn2—C13 | 123.32 (16) |
C2—Sn1—C1 | 123.91 (16) | C14—Sn2—C12 | 123.65 (15) |
C3—Sn1—C1 | 119.48 (16) | C13—Sn2—C12 | 111.22 (17) |
C2—Sn1—O1 | 97.74 (13) | C14—Sn2—O5 | 94.44 (13) |
C3—Sn1—O1 | 89.59 (12) | C13—Sn2—O5 | 90.53 (13) |
C1—Sn1—O1 | 98.56 (13) | C12—Sn2—O5 | 98.34 (12) |
C2—Sn1—O2i | 89.08 (13) | C14—Sn2—O6iii | 83.62 (12) |
C3—Sn1—O2i | 83.66 (12) | C13—Sn2—O6iii | 82.81 (12) |
C1—Sn1—O2i | 81.03 (12) | C12—Sn2—O6iii | 90.47 (12) |
O1—Sn1—O2i | 171.92 (9) | O5—Sn2—O6iii | 170.46 (9) |
C4—O1—Sn1 | 121.0 (2) | C15—O5—Sn2 | 123.5 (2) |
C4—O2—Sn1ii | 161.9 (3) | C15—O6—Sn2iv | 157.1 (2) |
C8—N1—C11 | 108.5 (3) | C22—N2—C19 | 109.8 (3) |
C8—N1—C5 | 123.2 (3) | C22—N2—C16 | 119.7 (3) |
C11—N1—C5 | 127.1 (4) | C19—N2—C16 | 130.5 (3) |
Sn1—C1—H1A | 109.5 | Sn2—C12—H12A | 109.5 |
Sn1—C1—H1B | 109.5 | Sn2—C12—H12B | 109.5 |
H1A—C1—H1B | 109.5 | H12A—C12—H12B | 109.5 |
Sn1—C1—H1C | 109.5 | Sn2—C12—H12C | 109.5 |
H1A—C1—H1C | 109.5 | H12A—C12—H12C | 109.5 |
H1B—C1—H1C | 109.5 | H12B—C12—H12C | 109.5 |
Sn1—C2—H2A | 109.5 | Sn2—C13—H13A | 109.5 |
Sn1—C2—H2B | 109.5 | Sn2—C13—H13B | 109.5 |
H2A—C2—H2B | 109.5 | H13A—C13—H13B | 109.5 |
Sn1—C2—H2C | 109.5 | Sn2—C13—H13C | 109.5 |
H2A—C2—H2C | 109.5 | H13A—C13—H13C | 109.5 |
H2B—C2—H2C | 109.5 | H13B—C13—H13C | 109.5 |
Sn1—C3—H3A | 109.5 | Sn2—C14—H14A | 109.5 |
Sn1—C3—H3B | 109.5 | Sn2—C14—H14B | 109.5 |
H3A—C3—H3B | 109.5 | H14A—C14—H14B | 109.5 |
Sn1—C3—H3C | 109.5 | Sn2—C14—H14C | 109.5 |
H3A—C3—H3C | 109.5 | H14A—C14—H14C | 109.5 |
H3B—C3—H3C | 109.5 | H14B—C14—H14C | 109.5 |
O2—C4—O1 | 125.2 (3) | O6—C15—O5 | 125.1 (3) |
O2—C4—C5 | 121.4 (3) | O6—C15—C16 | 119.7 (3) |
O1—C4—C5 | 113.1 (3) | O5—C15—C16 | 114.9 (3) |
N1—C5—C6 | 108.6 (3) | N2—C16—C17 | 109.5 (3) |
N1—C5—C7 | 110.5 (3) | N2—C16—C18 | 112.2 (3) |
C6—C5—C7 | 111.7 (4) | C17—C16—C18 | 110.3 (3) |
N1—C5—C4 | 108.8 (3) | N2—C16—C15 | 107.5 (3) |
C6—C5—C4 | 111.7 (3) | C17—C16—C15 | 112.5 (3) |
C7—C5—C4 | 105.5 (3) | C18—C16—C15 | 104.8 (3) |
C5—C6—H6A | 109.5 | C16—C17—H17A | 109.5 |
C5—C6—H6B | 109.5 | C16—C17—H17B | 109.5 |
H6A—C6—H6B | 109.5 | H17A—C17—H17B | 109.5 |
C5—C6—H6C | 109.5 | C16—C17—H17C | 109.5 |
H6A—C6—H6C | 109.5 | H17A—C17—H17C | 109.5 |
H6B—C6—H6C | 109.5 | H17B—C17—H17C | 109.5 |
C5—C7—H7A | 109.5 | C16—C18—H18A | 109.5 |
C5—C7—H7B | 109.5 | C16—C18—H18B | 109.5 |
H7A—C7—H7B | 109.5 | H18A—C18—H18B | 109.5 |
C5—C7—H7C | 109.5 | C16—C18—H18C | 109.5 |
H7A—C7—H7C | 109.5 | H18A—C18—H18C | 109.5 |
H7B—C7—H7C | 109.5 | H18B—C18—H18C | 109.5 |
O3—C8—N1 | 124.8 (4) | O7—C19—N2 | 127.2 (4) |
O3—C8—C9 | 128.8 (4) | O7—C19—C20 | 127.6 (4) |
N1—C8—C9 | 106.3 (3) | N2—C19—C20 | 105.2 (4) |
C10—C9—C8 | 108.8 (4) | C21—C20—C19 | 110.3 (4) |
C10—C9—H9 | 125.6 | C21—C20—H20 | 124.9 |
C8—C9—H9 | 125.6 | C19—C20—H20 | 124.9 |
C9—C10—C11 | 109.2 (4) | C20—C21—C22 | 108.4 (4) |
C9—C10—H10 | 125.4 | C20—C21—H21 | 125.8 |
C11—C10—H10 | 125.4 | C22—C21—H21 | 125.8 |
O4—C11—N1 | 125.5 (4) | O8—C22—N2 | 125.1 (4) |
O4—C11—C10 | 127.7 (4) | O8—C22—C21 | 128.4 (4) |
N1—C11—C10 | 106.8 (4) | N2—C22—C21 | 106.4 (4) |
C2—Sn1—O1—C4 | 66.1 (3) | C14—Sn2—O5—C15 | 67.4 (3) |
C3—Sn1—O1—C4 | −179.8 (3) | C13—Sn2—O5—C15 | −169.1 (3) |
C1—Sn1—O1—C4 | −60.0 (3) | C12—Sn2—O5—C15 | −57.6 (3) |
Sn1ii—O2—C4—O1 | −129.0 (7) | Sn2iv—O6—C15—O5 | 122.1 (6) |
Sn1ii—O2—C4—C5 | 45.2 (11) | Sn2iv—O6—C15—C16 | −64.6 (8) |
Sn1—O1—C4—O2 | −5.7 (5) | Sn2—O5—C15—O6 | −5.4 (6) |
Sn1—O1—C4—C5 | 179.7 (2) | Sn2—O5—C15—C16 | −179.0 (2) |
C8—N1—C5—C6 | 85.5 (5) | C22—N2—C16—C17 | 71.4 (4) |
C11—N1—C5—C6 | −80.9 (5) | C19—N2—C16—C17 | −109.9 (4) |
C8—N1—C5—C7 | −151.7 (4) | C22—N2—C16—C18 | −165.8 (3) |
C11—N1—C5—C7 | 41.9 (5) | C19—N2—C16—C18 | 12.9 (5) |
C8—N1—C5—C4 | −36.3 (5) | C22—N2—C16—C15 | −51.1 (4) |
C11—N1—C5—C4 | 157.3 (4) | C19—N2—C16—C15 | 127.6 (4) |
O2—C4—C5—N1 | 132.7 (4) | O6—C15—C16—N2 | 149.7 (3) |
O1—C4—C5—N1 | −52.5 (5) | O5—C15—C16—N2 | −36.3 (4) |
O2—C4—C5—C6 | 12.8 (6) | O6—C15—C16—C17 | 29.1 (5) |
O1—C4—C5—C6 | −172.3 (4) | O5—C15—C16—C17 | −156.9 (3) |
O2—C4—C5—C7 | −108.7 (4) | O6—C15—C16—C18 | −90.8 (4) |
O1—C4—C5—C7 | 66.1 (4) | O5—C15—C16—C18 | 83.2 (4) |
C11—N1—C8—O3 | 171.1 (4) | C22—N2—C19—O7 | −177.9 (4) |
C5—N1—C8—O3 | 2.5 (6) | C16—N2—C19—O7 | 3.3 (7) |
C11—N1—C8—C9 | −5.3 (4) | C22—N2—C19—C20 | 0.8 (4) |
C5—N1—C8—C9 | −173.9 (3) | C16—N2—C19—C20 | −177.9 (3) |
O3—C8—C9—C10 | −173.2 (4) | O7—C19—C20—C21 | 177.6 (5) |
N1—C8—C9—C10 | 3.0 (5) | N2—C19—C20—C21 | −1.1 (5) |
C8—C9—C10—C11 | 0.5 (5) | C19—C20—C21—C22 | 0.9 (5) |
C8—N1—C11—O4 | −173.8 (4) | C19—N2—C22—O8 | −178.8 (4) |
C5—N1—C11—O4 | −5.7 (7) | C16—N2—C22—O8 | 0.2 (6) |
C8—N1—C11—C10 | 5.6 (5) | C19—N2—C22—C21 | −0.4 (4) |
C5—N1—C11—C10 | 173.7 (4) | C16—N2—C22—C21 | 178.6 (3) |
C9—C10—C11—O4 | 175.6 (5) | C20—C21—C22—O8 | 178.0 (5) |
C9—C10—C11—N1 | −3.8 (5) | C20—C21—C22—N2 | −0.3 (5) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, y+1/2, −z+1/2. |