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
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. |