Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008100/ci2300sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008100/ci2300Isup2.hkl |
CCDC reference: 640303
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.072
- Data-to-parameter ratio = 27.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. N2 .. 2.85 Ang.
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.02 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.08 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.00 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O1 .. 8.53 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O8 .. 8.77 su PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C29
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
[Sn(C4H9)2(C7H3N2O6)2]·C7H8 | F(000) = 1520 |
Mr = 747.28 | Dx = 1.563 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6685 reflections |
a = 20.4571 (10) Å | θ = 1.3–33.3° |
b = 7.0328 (3) Å | µ = 0.87 mm−1 |
c = 29.4029 (13) Å | T = 100 K |
β = 131.364 (3)° | Block, yellow |
V = 3174.9 (3) Å3 | 0.28 × 0.21 × 0.10 mm |
Z = 4 |
Bruker SMART APEX2 CCD area-detector diffractometer | 12186 independent reflections |
Radiation source: fine-focus sealed tube | 9858 reflections with I > 2σ(I)' |
Graphite monochromator | Rint = 0.065 |
Detector resolution: 8.33 pixels mm-1 | θmax = 33.3°, θmin = 1.3° |
ω scans | h = −31→31 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −10→10 |
Tmin = 0.814, Tmax = 0.915 | l = −45→44 |
98264 measured reflections |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | Only H-atom displacement parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0238P)2 + 2.1069P] where P = (Fo2 + 2Fc2)/3 |
12186 reflections | (Δ/σ)max = 0.001 |
447 parameters | Δρmax = 0.88 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. Analysis found for C29H32N4O12Sn: C 45.90, H 4.42, N 7.48, Sn 15.73%; calculated: C 46.61 H 4.32, N 7.50, Sn 15.88%. FT–IR (KBr, cm-1): ν(COO)as 1629, ν(COO)s 1345, ν(O—Sn—O) 644, ν(Sn—C) 544, ν(Sn—O) 467. 1H NMR: δ benzene protons 9.26–9.27 (2H, t, J = 1.9 Hz), 9.28 - 9.29 (4H, d, J = 2.4 Hz), toluene CH3 2.36 (3H, s), CH2 7.13–7.17 (3H, m), 7.23–7.27 (2H, m), butyl CH3 0.95–0.98 (6H, t, J = 7.5 Hz), CH2 1.45–1.54 (4H, hx, 7.3 Hz), CH2 1.78–1.86 (4H, qn, 7.4 Hz), CH2 7.23–7.27 (2H, m). 13C NMR: δ benzene carbons 122.92, 130.55, 134.78, 149.09; butyl 13.91, 26.17, 26.83, 27.10; COO 171.47. 119Sn NMR: δ -121.78. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.712743 (7) | 0.178790 (15) | 0.217209 (5) | 0.01640 (3) | |
O1 | 0.84805 (8) | 0.17963 (17) | 0.22720 (6) | 0.0207 (2) | |
O2 | 0.74068 (8) | 0.38823 (17) | 0.18035 (6) | 0.0205 (2) | |
O3 | 0.76417 (9) | 0.96996 (19) | 0.09787 (6) | 0.0295 (3) | |
O4 | 0.87987 (10) | 1.01696 (18) | 0.11050 (7) | 0.0302 (3) | |
O5 | 1.06042 (8) | 0.47573 (18) | 0.15679 (6) | 0.0254 (3) | |
O6 | 1.07677 (9) | 0.2591 (2) | 0.21607 (6) | 0.0291 (3) | |
O7 | 0.59726 (8) | 0.33789 (16) | 0.17297 (5) | 0.0191 (2) | |
O8 | 0.59367 (8) | 0.10322 (17) | 0.22132 (6) | 0.0204 (2) | |
O9 | 0.35495 (9) | 0.0898 (2) | 0.22366 (7) | 0.0330 (3) | |
O10 | 0.25371 (9) | 0.30336 (19) | 0.17495 (8) | 0.0334 (3) | |
O11 | 0.30084 (9) | 0.87194 (18) | 0.11020 (7) | 0.0304 (3) | |
O12 | 0.40058 (9) | 0.87896 (18) | 0.10397 (7) | 0.0289 (3) | |
N1 | 0.83429 (10) | 0.9190 (2) | 0.11444 (7) | 0.0216 (3) | |
N2 | 1.04013 (9) | 0.3986 (2) | 0.18331 (7) | 0.0203 (3) | |
N3 | 0.32245 (10) | 0.2349 (2) | 0.19340 (7) | 0.0217 (3) | |
N4 | 0.36059 (10) | 0.79952 (19) | 0.11617 (7) | 0.0211 (3) | |
C1 | 0.82338 (11) | 0.6231 (2) | 0.15430 (7) | 0.0178 (3) | |
H1A | 0.7745 | 0.6718 | 0.1464 | 0.027 (6)* | |
C2 | 0.86590 (11) | 0.7270 (2) | 0.14035 (8) | 0.0182 (3) | |
C3 | 0.93685 (11) | 0.6581 (2) | 0.14918 (7) | 0.0182 (3) | |
H3A | 0.9636 | 0.7285 | 0.1386 | 0.027 (6)* | |
C4 | 0.96610 (10) | 0.4787 (2) | 0.17459 (7) | 0.0168 (3) | |
C5 | 0.92861 (10) | 0.3717 (2) | 0.19154 (7) | 0.0168 (3) | |
H5A | 0.9515 | 0.2538 | 0.2100 | 0.019 (5)* | |
C6 | 0.85582 (10) | 0.4443 (2) | 0.18045 (7) | 0.0164 (3) | |
C7 | 0.81362 (11) | 0.3282 (2) | 0.19747 (7) | 0.0175 (3) | |
C8 | 0.44045 (10) | 0.2469 (2) | 0.19104 (7) | 0.0164 (3) | |
H8A | 0.4588 | 0.1273 | 0.2090 | 0.021 (5)* | |
C9 | 0.36942 (10) | 0.3338 (2) | 0.17835 (7) | 0.0166 (3) | |
C10 | 0.34083 (10) | 0.5132 (2) | 0.15300 (7) | 0.0177 (3) | |
H10A | 0.2928 | 0.5692 | 0.1447 | 0.022 (5)* | |
C11 | 0.38710 (10) | 0.6046 (2) | 0.14061 (7) | 0.0168 (3) | |
C12 | 0.45768 (10) | 0.5230 (2) | 0.15095 (7) | 0.0169 (3) | |
H12A | 0.4866 | 0.5875 | 0.1411 | 0.025 (5)* | |
C13 | 0.48405 (10) | 0.3423 (2) | 0.17637 (7) | 0.0159 (3) | |
C14 | 0.56232 (10) | 0.2519 (2) | 0.19118 (7) | 0.0173 (3) | |
C15 | 0.67434 (12) | −0.0655 (2) | 0.16267 (9) | 0.0250 (4) | |
H15A | 0.6935 | −0.1775 | 0.1879 | 0.038 (7)* | |
H15B | 0.7040 | −0.0650 | 0.1471 | 0.049 (7)* | |
C16 | 0.57681 (13) | −0.0812 (3) | 0.10951 (9) | 0.0301 (4) | |
H16A | 0.5474 | −0.1006 | 0.1248 | 0.042 (7)* | |
H16B | 0.5558 | 0.0373 | 0.0870 | 0.039 (7)* | |
C17 | 0.55362 (14) | −0.2442 (3) | 0.06669 (10) | 0.0328 (4) | |
H17A | 0.5731 | −0.3634 | 0.0888 | 0.027 (6)* | |
H17B | 0.5839 | −0.2266 | 0.0519 | 0.036 (6)* | |
C18 | 0.45590 (17) | −0.2547 (4) | 0.01298 (12) | 0.0485 (6) | |
H18A | 0.4438 | −0.3581 | −0.0130 | 0.060 (9)* | |
H18B | 0.4259 | −0.2751 | 0.0274 | 0.067 (9)* | |
H18C | 0.4365 | −0.1377 | −0.0093 | 0.076 (11)* | |
C19 | 0.78915 (11) | 0.2526 (2) | 0.30973 (8) | 0.0194 (3) | |
H19A | 0.8172 | 0.1383 | 0.3339 | 0.020 (5)* | |
H19B | 0.7504 | 0.2977 | 0.3157 | 0.030 (6)* | |
C20 | 0.85916 (11) | 0.4032 (2) | 0.33403 (8) | 0.0199 (3) | |
H20A | 0.8320 | 0.5210 | 0.3119 | 0.026 (5)* | |
H20B | 0.8981 | 0.3614 | 0.3279 | 0.026 (6)* | |
C21 | 0.91106 (12) | 0.4375 (3) | 0.40118 (8) | 0.0253 (4) | |
H21A | 0.9344 | 0.3173 | 0.4226 | 0.025 (5)* | |
H21B | 0.8722 | 0.4858 | 0.4066 | 0.033 (6)* | |
C22 | 0.98554 (14) | 0.5772 (3) | 0.42894 (9) | 0.0323 (4) | |
H22A | 1.0160 | 0.5931 | 0.4712 | 0.027 (6)* | |
H22B | 1.0250 | 0.5290 | 0.4245 | 0.060 (8)* | |
H22C | 0.9628 | 0.6976 | 0.4087 | 0.043 (7)* | |
C23 | 0.21418 (14) | 0.2743 (3) | 0.02105 (9) | 0.0327 (4) | |
H23A | 0.2032 | 0.1679 | 0.0338 | 0.042 (7)* | |
C24 | 0.27805 (14) | 0.2663 (3) | 0.01756 (9) | 0.0335 (5) | |
H24A | 0.3100 | 0.1551 | 0.0283 | 0.034 (6)* | |
C25 | 0.29501 (13) | 0.4234 (3) | −0.00181 (9) | 0.0315 (4) | |
H25A | 0.3385 | 0.4180 | −0.0038 | 0.028 (6)* | |
C26 | 0.24681 (13) | 0.5890 (3) | −0.01811 (8) | 0.0284 (4) | |
H26A | 0.2574 | 0.6942 | −0.0316 | 0.030 (6)* | |
C27 | 0.18297 (12) | 0.5967 (3) | −0.01439 (8) | 0.0275 (4) | |
H27A | 0.1510 | 0.7079 | −0.0253 | 0.038 (7)* | |
C28 | 0.16559 (13) | 0.4402 (3) | 0.00560 (9) | 0.0294 (4) | |
C29 | 0.09763 (16) | 0.4512 (4) | 0.01097 (11) | 0.0419 (5) | |
H29A | 0.0945 | 0.3317 | 0.0252 | 0.082 (11)* | |
H29B | 0.0421 | 0.4792 | −0.0280 | 0.064 (9)* | |
H29C | 0.1128 | 0.5498 | 0.0391 | 0.074 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01582 (5) | 0.01666 (5) | 0.02158 (6) | 0.00086 (4) | 0.01442 (5) | 0.00111 (4) |
O1 | 0.0201 (6) | 0.0222 (5) | 0.0237 (6) | 0.0012 (4) | 0.0162 (5) | 0.0043 (5) |
O2 | 0.0183 (6) | 0.0229 (5) | 0.0262 (6) | 0.0009 (4) | 0.0172 (5) | 0.0024 (5) |
O3 | 0.0348 (8) | 0.0258 (6) | 0.0382 (8) | 0.0103 (5) | 0.0285 (7) | 0.0070 (5) |
O4 | 0.0387 (8) | 0.0203 (6) | 0.0422 (8) | −0.0019 (5) | 0.0313 (7) | 0.0036 (5) |
O5 | 0.0282 (7) | 0.0274 (6) | 0.0341 (7) | −0.0049 (5) | 0.0264 (6) | −0.0040 (5) |
O6 | 0.0269 (7) | 0.0307 (7) | 0.0361 (8) | 0.0101 (5) | 0.0236 (7) | 0.0092 (6) |
O7 | 0.0176 (5) | 0.0218 (5) | 0.0233 (6) | 0.0026 (4) | 0.0159 (5) | 0.0023 (4) |
O8 | 0.0184 (6) | 0.0213 (5) | 0.0247 (6) | 0.0041 (4) | 0.0156 (5) | 0.0033 (5) |
O9 | 0.0268 (7) | 0.0349 (7) | 0.0421 (8) | 0.0078 (6) | 0.0247 (7) | 0.0194 (6) |
O10 | 0.0263 (7) | 0.0301 (7) | 0.0585 (10) | 0.0056 (5) | 0.0342 (8) | 0.0093 (6) |
O11 | 0.0334 (8) | 0.0217 (6) | 0.0458 (9) | 0.0112 (5) | 0.0302 (7) | 0.0075 (6) |
O12 | 0.0311 (7) | 0.0208 (6) | 0.0423 (8) | 0.0022 (5) | 0.0274 (7) | 0.0077 (5) |
N1 | 0.0294 (8) | 0.0181 (6) | 0.0243 (7) | 0.0011 (5) | 0.0206 (7) | 0.0009 (5) |
N2 | 0.0178 (7) | 0.0230 (7) | 0.0234 (7) | −0.0019 (5) | 0.0150 (6) | −0.0035 (5) |
N3 | 0.0198 (7) | 0.0228 (7) | 0.0274 (8) | 0.0012 (5) | 0.0177 (7) | 0.0035 (6) |
N4 | 0.0227 (7) | 0.0158 (6) | 0.0252 (7) | 0.0014 (5) | 0.0159 (6) | 0.0008 (5) |
C1 | 0.0174 (7) | 0.0194 (7) | 0.0190 (8) | −0.0002 (5) | 0.0131 (7) | −0.0002 (5) |
C2 | 0.0199 (8) | 0.0158 (7) | 0.0203 (8) | 0.0000 (5) | 0.0139 (7) | 0.0001 (5) |
C3 | 0.0188 (7) | 0.0191 (7) | 0.0198 (8) | −0.0035 (5) | 0.0140 (7) | −0.0022 (6) |
C4 | 0.0155 (7) | 0.0192 (7) | 0.0174 (7) | −0.0015 (5) | 0.0116 (6) | −0.0022 (5) |
C5 | 0.0163 (7) | 0.0177 (7) | 0.0172 (7) | −0.0007 (5) | 0.0114 (7) | −0.0001 (5) |
C6 | 0.0163 (7) | 0.0191 (7) | 0.0165 (7) | −0.0018 (5) | 0.0119 (6) | −0.0008 (5) |
C7 | 0.0181 (7) | 0.0187 (7) | 0.0189 (7) | −0.0022 (6) | 0.0135 (6) | −0.0017 (6) |
C8 | 0.0143 (7) | 0.0153 (6) | 0.0177 (7) | 0.0013 (5) | 0.0098 (6) | 0.0012 (5) |
C9 | 0.0158 (7) | 0.0182 (7) | 0.0180 (7) | −0.0005 (5) | 0.0120 (6) | −0.0002 (5) |
C10 | 0.0155 (7) | 0.0188 (7) | 0.0192 (8) | 0.0017 (5) | 0.0117 (7) | −0.0012 (5) |
C11 | 0.0167 (7) | 0.0143 (6) | 0.0186 (7) | 0.0017 (5) | 0.0114 (7) | 0.0015 (5) |
C12 | 0.0159 (7) | 0.0181 (7) | 0.0182 (7) | −0.0012 (5) | 0.0119 (6) | −0.0007 (5) |
C13 | 0.0141 (7) | 0.0173 (7) | 0.0168 (7) | 0.0001 (5) | 0.0105 (6) | −0.0009 (5) |
C14 | 0.0157 (7) | 0.0193 (7) | 0.0190 (8) | 0.0007 (5) | 0.0123 (7) | −0.0010 (6) |
C15 | 0.0265 (9) | 0.0208 (8) | 0.0340 (10) | −0.0003 (6) | 0.0226 (9) | −0.0032 (7) |
C16 | 0.0293 (10) | 0.0305 (9) | 0.0368 (11) | −0.0058 (7) | 0.0246 (9) | −0.0110 (8) |
C17 | 0.0389 (11) | 0.0287 (9) | 0.0379 (11) | −0.0092 (8) | 0.0285 (10) | −0.0114 (8) |
C18 | 0.0434 (14) | 0.0557 (15) | 0.0455 (14) | −0.0198 (12) | 0.0289 (13) | −0.0237 (12) |
C19 | 0.0185 (8) | 0.0220 (7) | 0.0221 (8) | −0.0005 (6) | 0.0153 (7) | 0.0004 (6) |
C20 | 0.0210 (8) | 0.0193 (7) | 0.0245 (8) | −0.0008 (6) | 0.0172 (7) | 0.0000 (6) |
C21 | 0.0274 (9) | 0.0257 (8) | 0.0243 (9) | −0.0037 (7) | 0.0177 (8) | −0.0007 (7) |
C22 | 0.0368 (11) | 0.0349 (10) | 0.0265 (10) | −0.0135 (8) | 0.0215 (9) | −0.0084 (8) |
C23 | 0.0383 (11) | 0.0225 (8) | 0.0223 (9) | −0.0016 (7) | 0.0136 (9) | 0.0018 (7) |
C24 | 0.0370 (11) | 0.0231 (8) | 0.0214 (9) | 0.0078 (8) | 0.0111 (9) | 0.0006 (7) |
C25 | 0.0280 (10) | 0.0342 (10) | 0.0222 (9) | 0.0023 (8) | 0.0122 (8) | −0.0022 (7) |
C26 | 0.0274 (9) | 0.0237 (8) | 0.0211 (9) | −0.0014 (7) | 0.0105 (8) | 0.0002 (7) |
C27 | 0.0261 (9) | 0.0205 (8) | 0.0226 (9) | 0.0019 (7) | 0.0104 (8) | 0.0025 (6) |
C28 | 0.0277 (10) | 0.0273 (9) | 0.0210 (9) | −0.0010 (7) | 0.0108 (8) | 0.0003 (7) |
C29 | 0.0371 (12) | 0.0445 (13) | 0.0394 (13) | −0.0004 (10) | 0.0233 (11) | 0.0062 (10) |
Sn1—O7 | 2.1127 (11) | C15—C16 | 1.521 (3) |
Sn1—C15 | 2.1155 (17) | C15—H15A | 0.97 |
Sn1—O2 | 2.1188 (12) | C15—H15B | 0.97 |
Sn1—C19 | 2.1197 (17) | C16—C17 | 1.528 (3) |
O1—C7 | 1.2404 (19) | C16—H16A | 0.97 |
O2—C7 | 1.2904 (19) | C16—H16B | 0.97 |
O3—N1 | 1.2245 (19) | C17—C18 | 1.524 (3) |
O4—N1 | 1.2249 (19) | C17—H17A | 0.97 |
O5—N2 | 1.2255 (18) | C17—H17B | 0.97 |
O6—N2 | 1.224 (2) | C18—H18A | 0.96 |
O7—C14 | 1.2920 (19) | C18—H18B | 0.96 |
O8—C14 | 1.240 (2) | C18—H18C | 0.96 |
O9—N3 | 1.2221 (19) | C19—C20 | 1.527 (2) |
O10—N3 | 1.2229 (19) | C19—H19A | 0.97 |
O11—N4 | 1.2251 (19) | C19—H19B | 0.97 |
O12—N4 | 1.2237 (19) | C20—C21 | 1.521 (2) |
N1—C2 | 1.474 (2) | C20—H20A | 0.97 |
N2—C4 | 1.471 (2) | C20—H20B | 0.97 |
N3—C9 | 1.471 (2) | C21—C22 | 1.520 (3) |
N4—C11 | 1.474 (2) | C21—H21A | 0.97 |
C1—C2 | 1.389 (2) | C21—H21B | 0.97 |
C1—C6 | 1.392 (2) | C22—H22A | 0.96 |
C1—H1A | 0.93 | C22—H22B | 0.96 |
C2—C3 | 1.382 (2) | C22—H22C | 0.96 |
C3—C4 | 1.384 (2) | C23—C24 | 1.378 (3) |
C3—H3A | 0.93 | C23—C28 | 1.400 (3) |
C4—C5 | 1.381 (2) | C23—H23A | 0.93 |
C5—C6 | 1.394 (2) | C24—C25 | 1.388 (3) |
C5—H5A | 0.93 | C24—H24A | 0.93 |
C6—C7 | 1.495 (2) | C25—C26 | 1.391 (3) |
C8—C9 | 1.381 (2) | C25—H25A | 0.93 |
C8—C13 | 1.393 (2) | C26—C27 | 1.382 (3) |
C8—H8A | 0.93 | C26—H26A | 0.93 |
C9—C10 | 1.383 (2) | C27—C28 | 1.400 (3) |
C10—C11 | 1.378 (2) | C27—H27A | 0.93 |
C10—H10A | 0.93 | C28—C29 | 1.501 (3) |
C11—C12 | 1.388 (2) | C29—H29A | 0.96 |
C12—C13 | 1.390 (2) | C29—H29B | 0.96 |
C12—H12A | 0.93 | C29—H29C | 0.96 |
C13—C14 | 1.495 (2) | ||
O7—Sn1—C15 | 105.03 (6) | H15A—C15—H15B | 107.6 |
O7—Sn1—O2 | 83.49 (4) | C15—C16—C17 | 112.54 (16) |
C15—Sn1—O2 | 105.51 (6) | C15—C16—H16A | 109.1 |
O7—Sn1—C19 | 103.69 (6) | C17—C16—H16A | 109.1 |
C15—Sn1—C19 | 139.57 (7) | C15—C16—H16B | 109.1 |
O2—Sn1—C19 | 105.48 (6) | C17—C16—H16B | 109.1 |
C7—O2—Sn1 | 101.90 (10) | H16A—C16—H16B | 107.8 |
C14—O7—Sn1 | 101.34 (10) | C18—C17—C16 | 111.75 (19) |
O3—N1—O4 | 124.24 (15) | C18—C17—H17A | 109.3 |
O3—N1—C2 | 118.19 (14) | C16—C17—H17A | 109.3 |
O4—N1—C2 | 117.57 (14) | C18—C17—H17B | 109.3 |
O6—N2—O5 | 124.53 (15) | C16—C17—H17B | 109.3 |
O6—N2—C4 | 117.94 (14) | H17A—C17—H17B | 107.9 |
O5—N2—C4 | 117.53 (14) | C17—C18—H18A | 109.4 |
O9—N3—O10 | 124.38 (15) | C17—C18—H18B | 109.5 |
O9—N3—C9 | 117.69 (14) | H18A—C18—H18B | 109.5 |
O10—N3—C9 | 117.92 (14) | C17—C18—H18C | 109.5 |
O12—N4—O11 | 124.41 (14) | H18A—C18—H18C | 109.5 |
O12—N4—C11 | 117.74 (14) | H18B—C18—H18C | 109.5 |
O11—N4—C11 | 117.85 (14) | C20—C19—Sn1 | 116.01 (11) |
C2—C1—C6 | 118.36 (15) | C20—C19—H19A | 108.3 |
C2—C1—H1A | 120.8 | Sn1—C19—H19A | 108.3 |
C6—C1—H1A | 120.8 | C20—C19—H19B | 108.3 |
C3—C2—C1 | 123.01 (15) | Sn1—C19—H19B | 108.3 |
C3—C2—N1 | 117.78 (14) | H19A—C19—H19B | 107.4 |
C1—C2—N1 | 119.21 (14) | C21—C20—C19 | 110.60 (14) |
C2—C3—C4 | 116.53 (15) | C21—C20—H20A | 109.5 |
C2—C3—H3A | 121.7 | C19—C20—H20A | 109.5 |
C4—C3—H3A | 121.7 | C21—C20—H20B | 109.5 |
C5—C4—C3 | 123.10 (15) | C19—C20—H20B | 109.5 |
C5—C4—N2 | 118.78 (14) | H20A—C20—H20B | 108.1 |
C3—C4—N2 | 118.11 (14) | C22—C21—C20 | 113.08 (15) |
C4—C5—C6 | 118.55 (15) | C22—C21—H21A | 109.0 |
C4—C5—H5A | 120.7 | C20—C21—H21A | 109.0 |
C6—C5—H5A | 120.7 | C22—C21—H21B | 108.9 |
C1—C6—C5 | 120.38 (14) | C20—C21—H21B | 109.0 |
C1—C6—C7 | 120.55 (14) | H21A—C21—H21B | 107.7 |
C5—C6—C7 | 119.06 (14) | C21—C22—H22A | 109.5 |
O1—C7—O2 | 121.49 (15) | C21—C22—H22B | 109.5 |
O1—C7—C6 | 120.76 (15) | H22A—C22—H22B | 109.5 |
O2—C7—C6 | 117.75 (14) | C21—C22—H22C | 109.5 |
C9—C8—C13 | 118.54 (14) | H22A—C22—H22C | 109.5 |
C9—C8—H8A | 120.8 | H22B—C22—H22C | 109.5 |
C13—C8—H8A | 120.7 | C24—C23—C28 | 121.01 (19) |
C8—C9—C10 | 122.96 (15) | C24—C23—H23A | 119.5 |
C8—C9—N3 | 119.27 (14) | C28—C23—H23A | 119.5 |
C10—C9—N3 | 117.76 (14) | C23—C24—C25 | 120.29 (18) |
C11—C10—C9 | 116.66 (14) | C23—C24—H24A | 119.8 |
C11—C10—H10A | 121.7 | C25—C24—H24A | 119.9 |
C9—C10—H10A | 121.7 | C24—C25—C26 | 119.7 (2) |
C10—C11—C12 | 123.08 (14) | C24—C25—H25A | 120.2 |
C10—C11—N4 | 117.85 (14) | C26—C25—H25A | 120.1 |
C12—C11—N4 | 119.06 (14) | C27—C26—C25 | 119.84 (18) |
C11—C12—C13 | 118.29 (14) | C27—C26—H26A | 120.1 |
C11—C12—H12A | 120.9 | C25—C26—H26A | 120.1 |
C13—C12—H12A | 120.8 | C26—C27—C28 | 121.20 (18) |
C12—C13—C8 | 120.44 (14) | C26—C27—H27A | 119.4 |
C12—C13—C14 | 120.37 (14) | C28—C27—H27A | 119.4 |
C8—C13—C14 | 119.12 (14) | C23—C28—C27 | 118.0 (2) |
O8—C14—O7 | 121.62 (14) | C23—C28—C29 | 121.14 (19) |
O8—C14—C13 | 120.99 (14) | C27—C28—C29 | 120.90 (19) |
O7—C14—C13 | 117.36 (14) | C28—C29—H29A | 109.5 |
C16—C15—Sn1 | 114.56 (12) | C28—C29—H29B | 109.4 |
C16—C15—H15A | 108.6 | H29A—C29—H29B | 109.5 |
Sn1—C15—H15A | 108.6 | C28—C29—H29C | 109.5 |
C16—C15—H15B | 108.6 | H29A—C29—H29C | 109.5 |
Sn1—C15—H15B | 108.6 | H29B—C29—H29C | 109.5 |
O7—Sn1—O2—C7 | −177.17 (10) | C8—C9—C10—C11 | −0.1 (2) |
C15—Sn1—O2—C7 | −73.32 (11) | N3—C9—C10—C11 | 178.55 (15) |
C19—Sn1—O2—C7 | 80.38 (11) | C9—C10—C11—C12 | 1.7 (2) |
C15—Sn1—O7—C14 | 81.07 (11) | C9—C10—C11—N4 | −177.25 (14) |
O2—Sn1—O7—C14 | −174.57 (10) | O12—N4—C11—C10 | −178.46 (16) |
C19—Sn1—O7—C14 | −70.18 (11) | O11—N4—C11—C10 | 2.5 (2) |
C6—C1—C2—C3 | 2.5 (3) | O12—N4—C11—C12 | 2.5 (2) |
C6—C1—C2—N1 | −178.08 (14) | O11—N4—C11—C12 | −176.52 (16) |
O3—N1—C2—C3 | 169.04 (16) | C10—C11—C12—C13 | −1.6 (2) |
O4—N1—C2—C3 | −10.4 (2) | N4—C11—C12—C13 | 177.34 (14) |
O3—N1—C2—C1 | −10.4 (2) | C11—C12—C13—C8 | −0.1 (2) |
O4—N1—C2—C1 | 170.07 (16) | C11—C12—C13—C14 | −177.05 (15) |
C1—C2—C3—C4 | −1.7 (2) | C9—C8—C13—C12 | 1.6 (2) |
N1—C2—C3—C4 | 178.88 (14) | C9—C8—C13—C14 | 178.58 (14) |
C2—C3—C4—C5 | −0.9 (2) | Sn1—O7—C14—O8 | −6.70 (18) |
C2—C3—C4—N2 | 178.53 (14) | Sn1—O7—C14—C13 | 171.19 (12) |
O6—N2—C4—C5 | −14.6 (2) | C12—C13—C14—O8 | 169.94 (15) |
O5—N2—C4—C5 | 164.86 (15) | C8—C13—C14—O8 | −7.0 (2) |
O6—N2—C4—C3 | 165.93 (16) | C12—C13—C14—O7 | −8.0 (2) |
O5—N2—C4—C3 | −14.6 (2) | C8—C13—C14—O7 | 175.07 (14) |
C3—C4—C5—C6 | 2.5 (2) | O7—Sn1—C15—C16 | −4.51 (15) |
N2—C4—C5—C6 | −176.90 (14) | O2—Sn1—C15—C16 | −91.81 (14) |
C2—C1—C6—C5 | −0.7 (2) | C19—Sn1—C15—C16 | 129.36 (14) |
C2—C1—C6—C7 | 178.79 (15) | Sn1—C15—C16—C17 | 172.11 (14) |
C4—C5—C6—C1 | −1.7 (2) | C15—C16—C17—C18 | −178.66 (19) |
C4—C5—C6—C7 | 178.82 (14) | O7—Sn1—C19—C20 | −99.13 (12) |
Sn1—O2—C7—O1 | 0.90 (18) | C15—Sn1—C19—C20 | 126.64 (13) |
Sn1—O2—C7—C6 | −178.92 (11) | O2—Sn1—C19—C20 | −12.20 (13) |
C1—C6—C7—O1 | −171.35 (15) | Sn1—C19—C20—C21 | −177.99 (11) |
C5—C6—C7—O1 | 8.2 (2) | C19—C20—C21—C22 | 176.39 (16) |
C1—C6—C7—O2 | 8.5 (2) | C28—C23—C24—C25 | −0.4 (3) |
C5—C6—C7—O2 | −172.01 (15) | C23—C24—C25—C26 | −0.4 (3) |
C13—C8—C9—C10 | −1.5 (2) | C24—C25—C26—C27 | 0.6 (3) |
C13—C8—C9—N3 | 179.85 (14) | C25—C26—C27—C28 | 0.0 (3) |
O9—N3—C9—C8 | 9.2 (2) | C24—C23—C28—C27 | 1.0 (3) |
O10—N3—C9—C8 | −170.98 (16) | C24—C23—C28—C29 | −178.3 (2) |
O9—N3—C9—C10 | −169.54 (16) | C26—C27—C28—C23 | −0.8 (3) |
O10—N3—C9—C10 | 10.3 (2) | C26—C27—C28—C29 | 178.50 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···O3i | 0.97 | 2.45 | 3.420 (4) | 172 |
C19—H19A···O5ii | 0.97 | 2.60 | 3.198 (3) | 120 |
C22—H22C···O5iii | 0.96 | 2.56 | 3.458 (3) | 156 |
C24—H24A···O12i | 0.93 | 2.59 | 3.427 (3) | 150 |
Symmetry codes: (i) x, y−1, z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2. |
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