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The diorganotin(IV) complexes of 5-[(
E)-2-aryldiazen-1-yl]-2-hydroxybenzoic acid are of interest because of their structural diversity in the crystalline state and their interesting biological activity. The structures of dimethylbis{2-hydroxy-5-[(
E)-2-(4-methylphenyl)diazen-1-yl]benzoato}tin(IV), [Sn(CH
3)
2(C
14H
11N
2O
3)
2], and di-
n-butylbis{2-hydroxy-5-[(
E)-2-(4-methylphenyl)diazen-1-yl]benzoato}tin(IV) benzene hemisolvate, [Sn(C
4H
9)
2(C
14H
11N
2O
3)
2]·0.5C
6H
6, exhibit the usual skew-trapezoidal bipyramidal coordination geometry observed for related complexes of this class. Each structure has two independent molecules of the Sn
IV complex in the asymmetric unit. In the dimethyltin structure, intermolecular O—H
O hydrogen bonds and a very weak Sn
O interaction link the independent molecules into dimers. The planar carboxylate ligands lend themselves to π–π stacking interactions and the diversity of supramolecular structural motifs formed by these interactions has been examined in detail for these two structures and four closely related analogues. While there are some recurring basic motifs amongst the observed stacking arrangements, such as dimers and step-like chains, variations through longitudinal slipping and inversion of the direction of the overlay add complexity. The π–π stacking motifs in the two title complexes are combinations of some of those observed in the other structures and are the most complex of the structures examined.
Supporting information
CCDC references: 1468791; 1468790
For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
(I) Dimethylbis{2-hydroxy-5-[(
E)-2-(4-methylphenyl)diazen-1-yl]benzoato}tin(IV)
top
Crystal data top
[Sn(CH3)2(C14H11N2O3)2] | F(000) = 1336 |
Mr = 659.25 | Dx = 1.541 Mg m−3 |
Triclinic, P1 | Melting point: 496 K |
a = 10.1883 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.9209 (1) Å | Cell parameters from 77568 reflections |
c = 23.0447 (2) Å | θ = 2.0–30.0° |
α = 102.3524 (4)° | µ = 0.95 mm−1 |
β = 95.2584 (4)° | T = 160 K |
γ = 104.1530 (5)° | Prism, yellow |
V = 2840.09 (4) Å3 | 0.30 × 0.20 × 0.11 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 16590 independent reflections |
Radiation source: Nonius FR590 sealed tube generator | 10414 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.070 |
Detector resolution: 9 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
φ and ω scans with κ offsets | h = −14→14 |
Absorption correction: multi-scan (Blessing, 1995) | k = −18→18 |
Tmin = 0.805, Tmax = 0.912 | l = −32→32 |
69932 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0441P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
16590 reflections | Δρmax = 1.65 e Å−3 |
763 parameters | Δρmin = −1.07 e Å−3 |
Special details top
Experimental. Solvent used: benzene
Cooling Device: Oxford Cryosystems Cryostream 700
Crystal mount: glued on a glass fibre
Mosaicity (deg.): 0.503 (1)
Frames collected: 758
Seconds exposure per frame: 15
Degrees rotation per frame: 1.0
Crystal-Detector distance (mm): 33.4 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.10136 (2) | 0.38257 (2) | 0.32223 (2) | 0.02512 (6) | |
O1 | 0.25573 (18) | 0.50245 (15) | 0.38461 (8) | 0.0285 (4) | |
O2 | 0.34413 (19) | 0.36401 (16) | 0.35559 (9) | 0.0337 (5) | |
O3 | 0.5996 (2) | 0.38169 (18) | 0.39426 (10) | 0.0363 (5) | |
H3 | 0.521 (4) | 0.353 (4) | 0.3804 (19) | 0.094 (17)* | |
O4 | −0.00723 (19) | 0.50043 (15) | 0.34064 (8) | 0.0311 (5) | |
O5 | −0.14973 (19) | 0.36505 (15) | 0.27117 (9) | 0.0314 (5) | |
O6 | −0.3961 (2) | 0.38172 (17) | 0.23716 (9) | 0.0336 (5) | |
H6 | −0.344 (3) | 0.350 (3) | 0.2374 (16) | 0.052 (12)* | |
N1 | 0.6293 (2) | 0.8055 (2) | 0.52231 (10) | 0.0304 (6) | |
N2 | 0.7395 (2) | 0.85626 (19) | 0.55732 (10) | 0.0304 (6) | |
N3 | −0.2189 (2) | 0.81187 (18) | 0.37749 (10) | 0.0266 (5) | |
N4 | −0.2911 (2) | 0.87516 (19) | 0.36858 (10) | 0.0293 (5) | |
C1 | 0.3583 (3) | 0.4601 (2) | 0.38642 (12) | 0.0263 (6) | |
C2 | 0.4893 (3) | 0.5268 (2) | 0.42365 (12) | 0.0239 (6) | |
C3 | 0.6026 (3) | 0.4841 (2) | 0.42542 (12) | 0.0272 (6) | |
C4 | 0.7282 (3) | 0.5489 (2) | 0.45927 (13) | 0.0308 (7) | |
H4 | 0.8056 | 0.5202 | 0.4599 | 0.037* | |
C5 | 0.7396 (3) | 0.6539 (2) | 0.49150 (12) | 0.0292 (7) | |
H5 | 0.8249 | 0.6974 | 0.5146 | 0.035* | |
C6 | 0.6270 (3) | 0.6975 (2) | 0.49066 (12) | 0.0262 (6) | |
C7 | 0.5031 (3) | 0.6339 (2) | 0.45627 (12) | 0.0273 (6) | |
H7 | 0.4268 | 0.6638 | 0.4550 | 0.033* | |
C8 | 0.7434 (3) | 0.9646 (2) | 0.58893 (12) | 0.0281 (6) | |
C9 | 0.6412 (3) | 1.0163 (3) | 0.58016 (14) | 0.0378 (8) | |
H9 | 0.5625 | 0.9795 | 0.5508 | 0.045* | |
C10 | 0.6540 (3) | 1.1212 (3) | 0.61410 (14) | 0.0399 (8) | |
H10 | 0.5831 | 1.1556 | 0.6082 | 0.048* | |
C11 | 0.7696 (3) | 1.1776 (2) | 0.65696 (13) | 0.0344 (7) | |
C12 | 0.8729 (3) | 1.1262 (2) | 0.66414 (13) | 0.0349 (7) | |
H12 | 0.9531 | 1.1637 | 0.6925 | 0.042* | |
C13 | 0.8601 (3) | 1.0205 (2) | 0.63025 (13) | 0.0328 (7) | |
H13 | 0.9316 | 0.9864 | 0.6354 | 0.039* | |
C14 | −0.1235 (3) | 0.4599 (2) | 0.30469 (12) | 0.0272 (6) | |
C15 | −0.2184 (3) | 0.5285 (2) | 0.30485 (12) | 0.0247 (6) | |
C16 | −0.3503 (3) | 0.4863 (2) | 0.27060 (12) | 0.0266 (6) | |
C17 | −0.4382 (3) | 0.5535 (2) | 0.27123 (13) | 0.0296 (7) | |
H17 | −0.5267 | 0.5252 | 0.2478 | 0.035* | |
C18 | −0.3987 (3) | 0.6600 (2) | 0.30525 (12) | 0.0282 (6) | |
H18 | −0.4602 | 0.7046 | 0.3055 | 0.034* | |
C19 | −0.2681 (3) | 0.7035 (2) | 0.33971 (12) | 0.0249 (6) | |
C20 | −0.1805 (3) | 0.6370 (2) | 0.33952 (12) | 0.0252 (6) | |
H20 | −0.0927 | 0.6656 | 0.3635 | 0.030* | |
C21 | −0.2457 (3) | 0.9831 (2) | 0.40756 (12) | 0.0257 (6) | |
C22 | −0.1456 (3) | 1.0157 (2) | 0.45712 (13) | 0.0365 (7) | |
H22 | −0.0990 | 0.9651 | 0.4670 | 0.044* | |
C23 | −0.1129 (3) | 1.1218 (2) | 0.49247 (13) | 0.0379 (8) | |
H23 | −0.0435 | 1.1432 | 0.5266 | 0.045* | |
C24 | −0.1792 (3) | 1.1978 (2) | 0.47928 (13) | 0.0290 (6) | |
C25 | −0.2793 (3) | 1.1641 (2) | 0.42959 (15) | 0.0398 (8) | |
H25 | −0.3264 | 1.2146 | 0.4198 | 0.048* | |
C26 | −0.3126 (3) | 1.0579 (2) | 0.39364 (14) | 0.0373 (8) | |
H26 | −0.3815 | 1.0364 | 0.3594 | 0.045* | |
C27 | 0.7830 (3) | 1.2919 (3) | 0.69461 (15) | 0.0473 (9) | |
H271 | 0.7147 | 1.2884 | 0.7219 | 0.071* | |
H272 | 0.7679 | 1.3395 | 0.6682 | 0.071* | |
H273 | 0.8750 | 1.3219 | 0.7180 | 0.071* | |
C28 | −0.1414 (3) | 1.3135 (2) | 0.51864 (14) | 0.0372 (8) | |
H281 | −0.2028 | 1.3539 | 0.5047 | 0.056* | |
H282 | −0.0466 | 1.3509 | 0.5164 | 0.056* | |
H283 | −0.1505 | 1.3108 | 0.5603 | 0.056* | |
C29 | 0.1619 (3) | 0.3892 (3) | 0.23862 (13) | 0.0387 (8) | |
H291 | 0.1713 | 0.4634 | 0.2327 | 0.058* | |
H292 | 0.0927 | 0.3358 | 0.2068 | 0.058* | |
H293 | 0.2499 | 0.3716 | 0.2371 | 0.058* | |
C30 | 0.0148 (3) | 0.2604 (2) | 0.36471 (14) | 0.0385 (8) | |
H301 | −0.0138 | 0.2942 | 0.4020 | 0.058* | |
H302 | 0.0826 | 0.2218 | 0.3741 | 0.058* | |
H303 | −0.0650 | 0.2079 | 0.3380 | 0.058* | |
Sn2 | −0.60835 (2) | 0.10939 (2) | 0.20193 (2) | 0.02463 (6) | |
O41 | −0.50211 (18) | 0.00346 (15) | 0.15816 (8) | 0.0288 (4) | |
O42 | −0.35771 (19) | 0.16857 (15) | 0.18648 (9) | 0.0315 (5) | |
O43 | −0.1099 (2) | 0.20069 (18) | 0.15594 (11) | 0.0387 (6) | |
H43 | −0.162 (4) | 0.214 (3) | 0.1736 (16) | 0.054 (13)* | |
O44 | −0.77008 (19) | −0.03372 (15) | 0.18092 (9) | 0.0319 (5) | |
O45 | −0.86084 (19) | 0.09139 (16) | 0.23033 (8) | 0.0323 (5) | |
O46 | −1.1085 (2) | 0.02763 (18) | 0.25580 (10) | 0.0376 (5) | |
H46 | −1.038 (3) | 0.073 (3) | 0.2515 (15) | 0.051 (11)* | |
N41 | −0.2835 (2) | −0.23287 (19) | 0.02011 (10) | 0.0292 (5) | |
N42 | −0.2053 (2) | −0.2628 (2) | −0.01555 (10) | 0.0306 (6) | |
N43 | −1.1311 (2) | −0.3884 (2) | 0.11860 (11) | 0.0314 (6) | |
N44 | −1.2365 (2) | −0.4641 (2) | 0.11707 (10) | 0.0313 (6) | |
C41 | −0.3834 (3) | 0.0701 (2) | 0.15825 (12) | 0.0265 (6) | |
C42 | −0.2859 (3) | 0.0273 (2) | 0.12326 (12) | 0.0247 (6) | |
C43 | −0.1556 (3) | 0.0956 (2) | 0.12328 (13) | 0.0287 (6) | |
C44 | −0.0657 (3) | 0.0551 (2) | 0.08834 (13) | 0.0318 (7) | |
H44 | 0.0222 | 0.1014 | 0.0880 | 0.038* | |
C45 | −0.1047 (3) | −0.0524 (2) | 0.05437 (13) | 0.0305 (7) | |
H45 | −0.0428 | −0.0798 | 0.0310 | 0.037* | |
C46 | −0.2346 (3) | −0.1215 (2) | 0.05404 (12) | 0.0269 (6) | |
C47 | −0.3226 (3) | −0.0808 (2) | 0.08837 (12) | 0.0269 (6) | |
H47 | −0.4106 | −0.1274 | 0.0883 | 0.032* | |
C48 | −0.2533 (3) | −0.3745 (2) | −0.04892 (12) | 0.0281 (6) | |
C49 | −0.3806 (3) | −0.4456 (2) | −0.04775 (13) | 0.0353 (7) | |
H49 | −0.4426 | −0.4196 | −0.0239 | 0.042* | |
C50 | −0.4164 (3) | −0.5536 (3) | −0.08129 (13) | 0.0383 (8) | |
H50 | −0.5030 | −0.6013 | −0.0802 | 0.046* | |
C51 | −0.3265 (3) | −0.5931 (2) | −0.11675 (13) | 0.0320 (7) | |
C52 | −0.2020 (3) | −0.5218 (3) | −0.11793 (13) | 0.0352 (7) | |
H52 | −0.1397 | −0.5479 | −0.1416 | 0.042* | |
C53 | −0.1657 (3) | −0.4131 (3) | −0.08544 (13) | 0.0332 (7) | |
H53 | −0.0809 | −0.3648 | −0.0881 | 0.040* | |
C54 | −0.8724 (3) | −0.0069 (2) | 0.20316 (12) | 0.0294 (6) | |
C55 | −1.0001 (3) | −0.0942 (2) | 0.19579 (12) | 0.0260 (6) | |
C56 | −1.1115 (3) | −0.0731 (2) | 0.22349 (12) | 0.0275 (6) | |
C57 | −1.2287 (3) | −0.1595 (2) | 0.21874 (12) | 0.0310 (7) | |
H57 | −1.3026 | −0.1460 | 0.2388 | 0.037* | |
C58 | −1.2383 (3) | −0.2631 (2) | 0.18551 (13) | 0.0306 (7) | |
H58 | −1.3189 | −0.3208 | 0.1824 | 0.037* | |
C59 | −1.1297 (3) | −0.2847 (2) | 0.15587 (12) | 0.0272 (6) | |
C60 | −1.0120 (3) | −0.2002 (2) | 0.16222 (12) | 0.0284 (6) | |
H60 | −0.9373 | −0.2149 | 0.1432 | 0.034* | |
C61 | −1.2412 (3) | −0.5668 (2) | 0.07783 (12) | 0.0281 (6) | |
C62 | −1.1566 (3) | −0.5803 (3) | 0.03444 (13) | 0.0368 (7) | |
H62 | −1.0901 | −0.5184 | 0.0293 | 0.044* | |
C63 | −1.1693 (3) | −0.6832 (3) | −0.00090 (13) | 0.0386 (8) | |
H63 | −1.1111 | −0.6916 | −0.0305 | 0.046* | |
C64 | −1.2655 (3) | −0.7757 (2) | 0.00558 (13) | 0.0328 (7) | |
C65 | −1.3511 (3) | −0.7603 (3) | 0.04800 (14) | 0.0396 (8) | |
H65 | −1.4193 | −0.8218 | 0.0524 | 0.047* | |
C66 | −1.3393 (3) | −0.6569 (2) | 0.08424 (14) | 0.0367 (7) | |
H66 | −1.3984 | −0.6480 | 0.1134 | 0.044* | |
C67 | −0.3666 (3) | −0.7128 (3) | −0.15153 (14) | 0.0426 (8) | |
H671 | −0.4312 | −0.7226 | −0.1878 | 0.064* | |
H672 | −0.4099 | −0.7593 | −0.1263 | 0.064* | |
H673 | −0.2847 | −0.7338 | −0.1630 | 0.064* | |
C68 | −1.2762 (3) | −0.8892 (3) | −0.03241 (13) | 0.0428 (8) | |
H681 | −1.2550 | −0.8838 | −0.0725 | 0.064* | |
H682 | −1.3695 | −0.9362 | −0.0360 | 0.064* | |
H683 | −1.2111 | −0.9211 | −0.0134 | 0.064* | |
C69 | −0.5492 (3) | 0.1368 (3) | 0.29454 (12) | 0.0376 (8) | |
H691 | −0.6033 | 0.1807 | 0.3163 | 0.056* | |
H692 | −0.4518 | 0.1764 | 0.3052 | 0.056* | |
H693 | −0.5647 | 0.0660 | 0.3055 | 0.056* | |
C70 | −0.6591 (3) | 0.1953 (2) | 0.13960 (13) | 0.0330 (7) | |
H701 | −0.6566 | 0.1540 | 0.0989 | 0.049* | |
H702 | −0.5931 | 0.2680 | 0.1482 | 0.049* | |
H703 | −0.7513 | 0.2041 | 0.1425 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.02441 (11) | 0.02026 (11) | 0.02735 (11) | 0.00554 (8) | 0.00105 (8) | 0.00053 (8) |
O1 | 0.0234 (10) | 0.0262 (11) | 0.0306 (11) | 0.0066 (9) | −0.0030 (8) | −0.0010 (8) |
O2 | 0.0301 (11) | 0.0228 (11) | 0.0426 (12) | 0.0067 (9) | 0.0002 (9) | −0.0009 (9) |
O3 | 0.0316 (13) | 0.0246 (12) | 0.0501 (14) | 0.0115 (10) | 0.0009 (10) | 0.0016 (10) |
O4 | 0.0254 (11) | 0.0260 (11) | 0.0372 (12) | 0.0095 (9) | −0.0035 (9) | −0.0017 (9) |
O5 | 0.0296 (11) | 0.0233 (11) | 0.0359 (12) | 0.0083 (9) | −0.0002 (9) | −0.0032 (9) |
O6 | 0.0261 (12) | 0.0244 (12) | 0.0407 (13) | 0.0030 (10) | −0.0044 (9) | −0.0039 (9) |
N1 | 0.0265 (13) | 0.0288 (14) | 0.0313 (13) | 0.0045 (11) | 0.0021 (10) | 0.0021 (11) |
N2 | 0.0287 (13) | 0.0272 (14) | 0.0319 (14) | 0.0046 (11) | 0.0008 (11) | 0.0047 (11) |
N3 | 0.0264 (13) | 0.0214 (13) | 0.0307 (13) | 0.0071 (10) | 0.0022 (10) | 0.0039 (10) |
N4 | 0.0297 (13) | 0.0247 (13) | 0.0337 (14) | 0.0082 (11) | 0.0055 (10) | 0.0063 (11) |
C1 | 0.0254 (15) | 0.0254 (16) | 0.0266 (15) | 0.0051 (12) | 0.0031 (12) | 0.0055 (12) |
C2 | 0.0224 (14) | 0.0252 (15) | 0.0246 (14) | 0.0062 (12) | 0.0024 (11) | 0.0079 (12) |
C3 | 0.0314 (16) | 0.0259 (16) | 0.0269 (15) | 0.0101 (13) | 0.0060 (12) | 0.0085 (12) |
C4 | 0.0239 (15) | 0.0325 (17) | 0.0372 (17) | 0.0102 (13) | 0.0013 (12) | 0.0097 (14) |
C5 | 0.0212 (15) | 0.0333 (17) | 0.0312 (16) | 0.0050 (13) | −0.0001 (12) | 0.0079 (13) |
C6 | 0.0266 (15) | 0.0264 (16) | 0.0243 (14) | 0.0058 (12) | 0.0039 (11) | 0.0052 (12) |
C7 | 0.0276 (15) | 0.0254 (16) | 0.0282 (15) | 0.0087 (13) | 0.0040 (12) | 0.0033 (12) |
C8 | 0.0298 (16) | 0.0250 (16) | 0.0273 (15) | 0.0036 (13) | 0.0036 (12) | 0.0062 (12) |
C9 | 0.0306 (17) | 0.0355 (19) | 0.0417 (19) | 0.0053 (14) | −0.0001 (14) | 0.0046 (15) |
C10 | 0.0354 (18) | 0.0325 (18) | 0.051 (2) | 0.0106 (15) | 0.0091 (15) | 0.0071 (15) |
C11 | 0.0419 (19) | 0.0252 (17) | 0.0328 (17) | 0.0017 (14) | 0.0129 (14) | 0.0055 (13) |
C12 | 0.0378 (18) | 0.0304 (18) | 0.0309 (16) | −0.0007 (14) | −0.0004 (13) | 0.0095 (13) |
C13 | 0.0333 (17) | 0.0253 (16) | 0.0360 (17) | 0.0027 (13) | 0.0003 (13) | 0.0077 (13) |
C14 | 0.0264 (15) | 0.0240 (16) | 0.0284 (15) | 0.0059 (12) | 0.0027 (12) | 0.0021 (12) |
C15 | 0.0261 (15) | 0.0236 (15) | 0.0229 (14) | 0.0053 (12) | 0.0030 (11) | 0.0047 (11) |
C16 | 0.0277 (15) | 0.0263 (16) | 0.0224 (14) | 0.0033 (13) | 0.0016 (11) | 0.0038 (12) |
C17 | 0.0203 (14) | 0.0301 (17) | 0.0342 (16) | 0.0031 (13) | 0.0005 (12) | 0.0050 (13) |
C18 | 0.0244 (15) | 0.0276 (16) | 0.0338 (16) | 0.0091 (13) | 0.0040 (12) | 0.0077 (13) |
C19 | 0.0239 (14) | 0.0216 (15) | 0.0273 (15) | 0.0033 (12) | 0.0025 (11) | 0.0060 (12) |
C20 | 0.0220 (14) | 0.0266 (16) | 0.0260 (15) | 0.0067 (12) | 0.0005 (11) | 0.0054 (12) |
C21 | 0.0257 (15) | 0.0236 (15) | 0.0285 (15) | 0.0083 (12) | 0.0060 (12) | 0.0051 (12) |
C22 | 0.0438 (19) | 0.0282 (17) | 0.0385 (18) | 0.0182 (15) | −0.0039 (14) | 0.0045 (14) |
C23 | 0.046 (2) | 0.0337 (18) | 0.0327 (17) | 0.0169 (16) | −0.0036 (14) | 0.0022 (14) |
C24 | 0.0275 (16) | 0.0263 (16) | 0.0350 (16) | 0.0085 (13) | 0.0113 (13) | 0.0073 (13) |
C25 | 0.0376 (18) | 0.0252 (17) | 0.059 (2) | 0.0165 (15) | −0.0045 (16) | 0.0104 (15) |
C26 | 0.0335 (17) | 0.0300 (18) | 0.0449 (19) | 0.0109 (14) | −0.0120 (14) | 0.0065 (14) |
C27 | 0.056 (2) | 0.0306 (19) | 0.050 (2) | 0.0054 (17) | 0.0137 (17) | 0.0038 (16) |
C28 | 0.0387 (18) | 0.0283 (17) | 0.0425 (19) | 0.0126 (15) | 0.0060 (14) | 0.0002 (14) |
C29 | 0.0324 (17) | 0.045 (2) | 0.0311 (17) | −0.0008 (15) | 0.0072 (13) | 0.0050 (15) |
C30 | 0.0430 (19) | 0.0277 (17) | 0.0409 (19) | 0.0022 (15) | 0.0030 (15) | 0.0100 (14) |
Sn2 | 0.02260 (11) | 0.02230 (11) | 0.02507 (11) | 0.00392 (8) | 0.00101 (8) | 0.00108 (8) |
O41 | 0.0215 (10) | 0.0234 (11) | 0.0358 (11) | 0.0027 (8) | 0.0050 (8) | −0.0012 (9) |
O42 | 0.0274 (11) | 0.0230 (11) | 0.0370 (12) | 0.0042 (9) | 0.0034 (9) | −0.0043 (9) |
O43 | 0.0268 (12) | 0.0280 (13) | 0.0500 (15) | −0.0013 (10) | 0.0048 (11) | −0.0035 (10) |
O44 | 0.0265 (11) | 0.0259 (11) | 0.0357 (12) | −0.0010 (9) | 0.0071 (9) | −0.0004 (9) |
O45 | 0.0304 (11) | 0.0260 (11) | 0.0339 (11) | 0.0018 (9) | 0.0026 (9) | 0.0012 (9) |
O46 | 0.0378 (13) | 0.0275 (13) | 0.0409 (13) | 0.0030 (11) | 0.0115 (10) | −0.0010 (10) |
N41 | 0.0281 (13) | 0.0256 (14) | 0.0338 (14) | 0.0080 (11) | 0.0049 (11) | 0.0062 (11) |
N42 | 0.0330 (14) | 0.0310 (14) | 0.0302 (13) | 0.0128 (12) | 0.0042 (11) | 0.0078 (11) |
N43 | 0.0280 (13) | 0.0286 (14) | 0.0340 (14) | 0.0031 (11) | 0.0069 (11) | 0.0045 (11) |
N44 | 0.0298 (14) | 0.0272 (14) | 0.0346 (14) | 0.0039 (11) | 0.0069 (11) | 0.0066 (11) |
C41 | 0.0236 (15) | 0.0242 (16) | 0.0277 (15) | 0.0045 (12) | −0.0021 (11) | 0.0027 (12) |
C42 | 0.0197 (14) | 0.0249 (15) | 0.0267 (15) | 0.0035 (12) | 0.0011 (11) | 0.0046 (12) |
C43 | 0.0232 (15) | 0.0257 (16) | 0.0333 (16) | 0.0035 (12) | −0.0026 (12) | 0.0058 (13) |
C44 | 0.0202 (15) | 0.0352 (18) | 0.0359 (17) | 0.0013 (13) | 0.0021 (12) | 0.0085 (14) |
C45 | 0.0251 (15) | 0.0369 (18) | 0.0333 (16) | 0.0133 (14) | 0.0058 (12) | 0.0102 (14) |
C46 | 0.0268 (15) | 0.0265 (16) | 0.0262 (15) | 0.0056 (13) | 0.0028 (12) | 0.0062 (12) |
C47 | 0.0229 (14) | 0.0279 (16) | 0.0281 (15) | 0.0040 (12) | 0.0011 (11) | 0.0076 (12) |
C48 | 0.0304 (16) | 0.0280 (16) | 0.0268 (15) | 0.0102 (13) | 0.0019 (12) | 0.0070 (12) |
C49 | 0.0322 (17) | 0.0362 (19) | 0.0354 (17) | 0.0106 (14) | 0.0098 (13) | 0.0007 (14) |
C50 | 0.0310 (17) | 0.0387 (19) | 0.0390 (18) | 0.0050 (15) | 0.0026 (14) | 0.0024 (15) |
C51 | 0.0370 (17) | 0.0314 (17) | 0.0280 (16) | 0.0113 (14) | 0.0023 (13) | 0.0066 (13) |
C52 | 0.0429 (19) | 0.0358 (19) | 0.0316 (17) | 0.0180 (16) | 0.0131 (14) | 0.0067 (14) |
C53 | 0.0311 (16) | 0.0372 (18) | 0.0326 (16) | 0.0095 (14) | 0.0076 (13) | 0.0099 (14) |
C54 | 0.0310 (16) | 0.0295 (17) | 0.0237 (15) | 0.0033 (13) | 0.0018 (12) | 0.0050 (12) |
C55 | 0.0227 (14) | 0.0275 (16) | 0.0245 (14) | 0.0037 (12) | 0.0025 (11) | 0.0039 (12) |
C56 | 0.0299 (16) | 0.0266 (16) | 0.0235 (14) | 0.0065 (13) | 0.0007 (12) | 0.0037 (12) |
C57 | 0.0254 (15) | 0.0347 (18) | 0.0307 (16) | 0.0047 (13) | 0.0084 (12) | 0.0057 (13) |
C58 | 0.0260 (15) | 0.0291 (17) | 0.0340 (16) | 0.0017 (13) | 0.0071 (12) | 0.0075 (13) |
C59 | 0.0255 (15) | 0.0254 (16) | 0.0308 (16) | 0.0059 (12) | 0.0060 (12) | 0.0073 (12) |
C60 | 0.0253 (15) | 0.0325 (17) | 0.0262 (15) | 0.0055 (13) | 0.0056 (12) | 0.0065 (12) |
C61 | 0.0261 (15) | 0.0258 (16) | 0.0316 (16) | 0.0056 (13) | 0.0046 (12) | 0.0071 (13) |
C62 | 0.0297 (17) | 0.0408 (19) | 0.0359 (17) | 0.0024 (14) | 0.0090 (13) | 0.0075 (15) |
C63 | 0.0341 (18) | 0.046 (2) | 0.0307 (17) | 0.0077 (16) | 0.0085 (13) | 0.0004 (15) |
C64 | 0.0344 (17) | 0.0338 (18) | 0.0270 (16) | 0.0109 (14) | −0.0028 (13) | 0.0017 (13) |
C65 | 0.0434 (19) | 0.0279 (18) | 0.0436 (19) | 0.0027 (15) | 0.0069 (15) | 0.0085 (15) |
C66 | 0.0416 (19) | 0.0303 (18) | 0.0372 (18) | 0.0058 (15) | 0.0159 (14) | 0.0061 (14) |
C67 | 0.051 (2) | 0.037 (2) | 0.0388 (19) | 0.0152 (16) | 0.0123 (15) | 0.0007 (15) |
C68 | 0.052 (2) | 0.040 (2) | 0.0330 (18) | 0.0188 (17) | −0.0033 (15) | −0.0020 (15) |
C69 | 0.0452 (19) | 0.0366 (19) | 0.0267 (16) | 0.0110 (15) | −0.0026 (14) | 0.0020 (14) |
C70 | 0.0264 (16) | 0.0391 (19) | 0.0338 (17) | 0.0063 (14) | 0.0009 (13) | 0.0141 (14) |
Geometric parameters (Å, º) top
Sn1—O1 | 2.0930 (17) | Sn2—O41 | 2.0966 (17) |
Sn1—O2 | 2.6051 (18) | Sn2—O42 | 2.5613 (19) |
Sn1—O4 | 2.0872 (17) | Sn2—O44 | 2.0855 (19) |
Sn1—O5 | 2.6517 (18) | Sn2—O45 | 2.6798 (19) |
Sn1—C29 | 2.089 (3) | Sn2—C69 | 2.093 (3) |
Sn1—C30 | 2.090 (3) | Sn2—C70 | 2.095 (3) |
O1—C1 | 1.294 (3) | O41—C41 | 1.302 (3) |
O2—C1 | 1.258 (3) | O42—C41 | 1.250 (3) |
O3—C3 | 1.355 (3) | O43—C43 | 1.348 (3) |
O3—H3 | 0.80 (4) | O43—H43 | 0.72 (3) |
O4—C14 | 1.302 (3) | O44—C54 | 1.292 (3) |
O5—C14 | 1.251 (3) | O45—C54 | 1.261 (3) |
O6—C16 | 1.348 (3) | O46—C56 | 1.346 (3) |
O6—H6 | 0.75 (3) | O46—H46 | 0.84 (3) |
N1—N2 | 1.261 (3) | N41—N42 | 1.262 (3) |
N1—C6 | 1.423 (3) | N41—C46 | 1.423 (3) |
N2—C8 | 1.422 (3) | N42—C48 | 1.423 (3) |
N3—N4 | 1.261 (3) | N43—N44 | 1.256 (3) |
N3—C19 | 1.423 (3) | N43—C59 | 1.424 (3) |
N4—C21 | 1.427 (3) | N44—C61 | 1.424 (3) |
C1—C2 | 1.474 (4) | C41—C42 | 1.472 (4) |
C2—C7 | 1.393 (4) | C42—C47 | 1.395 (4) |
C2—C3 | 1.397 (4) | C42—C43 | 1.402 (4) |
C3—C4 | 1.401 (4) | C43—C44 | 1.397 (4) |
C4—C5 | 1.372 (4) | C44—C45 | 1.381 (4) |
C4—H4 | 0.9500 | C44—H44 | 0.9500 |
C5—C6 | 1.396 (4) | C45—C46 | 1.402 (4) |
C5—H5 | 0.9500 | C45—H45 | 0.9500 |
C6—C7 | 1.388 (4) | C46—C47 | 1.375 (4) |
C7—H7 | 0.9500 | C47—H47 | 0.9500 |
C8—C13 | 1.385 (4) | C48—C53 | 1.388 (4) |
C8—C9 | 1.390 (4) | C48—C49 | 1.401 (4) |
C9—C10 | 1.381 (4) | C49—C50 | 1.384 (4) |
C9—H9 | 0.9500 | C49—H49 | 0.9500 |
C10—C11 | 1.398 (4) | C50—C51 | 1.399 (4) |
C10—H10 | 0.9500 | C50—H50 | 0.9500 |
C11—C12 | 1.390 (4) | C51—C52 | 1.380 (4) |
C11—C27 | 1.512 (4) | C51—C67 | 1.517 (4) |
C12—C13 | 1.389 (4) | C52—C53 | 1.384 (4) |
C12—H12 | 0.9500 | C52—H52 | 0.9500 |
C13—H13 | 0.9500 | C53—H53 | 0.9500 |
C14—C15 | 1.463 (4) | C54—C55 | 1.468 (4) |
C15—C20 | 1.396 (4) | C55—C60 | 1.392 (4) |
C15—C16 | 1.411 (4) | C55—C56 | 1.407 (4) |
C16—C17 | 1.390 (4) | C56—C57 | 1.399 (4) |
C17—C18 | 1.372 (4) | C57—C58 | 1.369 (4) |
C17—H17 | 0.9500 | C57—H57 | 0.9500 |
C18—C19 | 1.402 (4) | C58—C59 | 1.406 (4) |
C18—H18 | 0.9500 | C58—H58 | 0.9500 |
C19—C20 | 1.382 (4) | C59—C60 | 1.382 (4) |
C20—H20 | 0.9500 | C60—H60 | 0.9500 |
C21—C22 | 1.375 (4) | C61—C66 | 1.381 (4) |
C21—C26 | 1.385 (4) | C61—C62 | 1.389 (4) |
C22—C23 | 1.379 (4) | C62—C63 | 1.371 (4) |
C22—H22 | 0.9500 | C62—H62 | 0.9500 |
C23—C24 | 1.389 (4) | C63—C64 | 1.394 (4) |
C23—H23 | 0.9500 | C63—H63 | 0.9500 |
C24—C25 | 1.377 (4) | C64—C65 | 1.383 (4) |
C24—C28 | 1.510 (4) | C64—C68 | 1.510 (4) |
C25—C26 | 1.385 (4) | C65—C66 | 1.387 (4) |
C25—H25 | 0.9500 | C65—H65 | 0.9500 |
C26—H26 | 0.9500 | C66—H66 | 0.9500 |
C27—H271 | 0.9800 | C67—H671 | 0.9800 |
C27—H272 | 0.9800 | C67—H672 | 0.9800 |
C27—H273 | 0.9800 | C67—H673 | 0.9800 |
C28—H281 | 0.9800 | C68—H681 | 0.9800 |
C28—H282 | 0.9800 | C68—H682 | 0.9800 |
C28—H283 | 0.9800 | C68—H683 | 0.9800 |
C29—H291 | 0.9800 | C69—H691 | 0.9800 |
C29—H292 | 0.9800 | C69—H692 | 0.9800 |
C29—H293 | 0.9800 | C69—H693 | 0.9800 |
C30—H301 | 0.9800 | C70—H701 | 0.9800 |
C30—H302 | 0.9800 | C70—H702 | 0.9800 |
C30—H303 | 0.9800 | C70—H703 | 0.9800 |
| | | |
O1—Sn1—O4 | 82.93 (7) | O41—Sn2—O44 | 83.06 (7) |
O1—Sn1—O5 | 136.76 (6) | O41—Sn2—O45 | 136.67 (7) |
O1—Sn1—C29 | 104.91 (10) | O41—Sn2—C69 | 107.65 (10) |
O1—Sn1—C30 | 107.95 (10) | O41—Sn2—C70 | 105.62 (10) |
O2—Sn1—O4 | 137.49 (7) | O42—Sn2—O44 | 138.31 (6) |
O2—Sn1—O5 | 168.41 (6) | O42—Sn2—O45 | 168.07 (6) |
O2—Sn1—C29 | 86.97 (10) | O42—Sn2—C69 | 90.91 (10) |
O2—Sn1—C30 | 89.97 (10) | O42—Sn2—C70 | 89.12 (9) |
O4—Sn1—C29 | 105.62 (11) | O44—Sn2—C69 | 103.72 (11) |
O4—Sn1—C30 | 105.34 (10) | O44—Sn2—C70 | 103.02 (10) |
O5—Sn1—C29 | 86.87 (10) | O45—Sn2—C69 | 84.44 (10) |
O5—Sn1—C30 | 87.83 (10) | O45—Sn2—C70 | 87.28 (9) |
C29—Sn1—C30 | 136.93 (12) | C69—Sn2—C70 | 139.25 (12) |
O1—Sn1—O2 | 54.57 (6) | O41—Sn2—O42 | 55.25 (6) |
O4—Sn1—O5 | 53.89 (6) | O44—Sn2—O45 | 53.62 (6) |
C1—O1—Sn1 | 104.55 (16) | C41—O41—Sn2 | 102.78 (16) |
C1—O2—Sn1 | 81.64 (15) | C41—O42—Sn2 | 82.61 (16) |
C3—O3—H3 | 105 (3) | C43—O43—H43 | 109 (3) |
C14—O4—Sn1 | 105.80 (16) | C54—O44—Sn2 | 106.52 (17) |
C14—O5—Sn1 | 80.75 (15) | C54—O45—Sn2 | 79.59 (16) |
C16—O6—H6 | 113 (3) | C56—O46—H46 | 109 (2) |
N2—N1—C6 | 113.8 (2) | N42—N41—C46 | 114.2 (2) |
N1—N2—C8 | 114.3 (2) | N41—N42—C48 | 114.3 (2) |
N4—N3—C19 | 113.9 (2) | N44—N43—C59 | 114.0 (2) |
N3—N4—C21 | 114.5 (2) | N43—N44—C61 | 114.2 (2) |
O2—C1—O1 | 119.2 (2) | O42—C41—O41 | 119.0 (2) |
O2—C1—C2 | 121.9 (2) | O42—C41—C42 | 122.4 (3) |
O1—C1—C2 | 118.9 (2) | O41—C41—C42 | 118.5 (2) |
C7—C2—C3 | 119.1 (3) | C47—C42—C43 | 118.8 (3) |
C7—C2—C1 | 120.7 (2) | C47—C42—C41 | 120.7 (2) |
C3—C2—C1 | 120.2 (2) | C43—C42—C41 | 120.4 (2) |
O3—C3—C2 | 123.2 (3) | O43—C43—C44 | 116.7 (3) |
O3—C3—C4 | 116.7 (3) | O43—C43—C42 | 123.4 (3) |
C2—C3—C4 | 120.1 (3) | C44—C43—C42 | 119.9 (3) |
C5—C4—C3 | 120.0 (3) | C45—C44—C43 | 119.9 (3) |
C5—C4—H4 | 120.0 | C45—C44—H44 | 120.0 |
C3—C4—H4 | 120.0 | C43—C44—H44 | 120.0 |
C4—C5—C6 | 120.6 (3) | C44—C45—C46 | 120.7 (3) |
C4—C5—H5 | 119.7 | C44—C45—H45 | 119.6 |
C6—C5—H5 | 119.7 | C46—C45—H45 | 119.6 |
C7—C6—C5 | 119.4 (3) | C47—C46—C45 | 118.9 (3) |
C7—C6—N1 | 116.1 (2) | C47—C46—N41 | 116.6 (2) |
C5—C6—N1 | 124.6 (3) | C45—C46—N41 | 124.5 (3) |
C6—C7—C2 | 120.8 (3) | C46—C47—C42 | 121.7 (3) |
C6—C7—H7 | 119.6 | C46—C47—H47 | 119.2 |
C2—C7—H7 | 119.6 | C42—C47—H47 | 119.2 |
C13—C8—C9 | 119.6 (3) | C53—C48—C49 | 119.1 (3) |
C13—C8—N2 | 115.8 (3) | C53—C48—N42 | 116.1 (3) |
C9—C8—N2 | 124.6 (3) | C49—C48—N42 | 124.8 (3) |
C10—C9—C8 | 120.0 (3) | C50—C49—C48 | 120.2 (3) |
C10—C9—H9 | 120.0 | C50—C49—H49 | 119.9 |
C8—C9—H9 | 120.0 | C48—C49—H49 | 119.9 |
C9—C10—C11 | 121.1 (3) | C49—C50—C51 | 120.6 (3) |
C9—C10—H10 | 119.5 | C49—C50—H50 | 119.7 |
C11—C10—H10 | 119.5 | C51—C50—H50 | 119.7 |
C12—C11—C10 | 118.4 (3) | C52—C51—C50 | 118.5 (3) |
C12—C11—C27 | 120.5 (3) | C52—C51—C67 | 122.0 (3) |
C10—C11—C27 | 121.1 (3) | C50—C51—C67 | 119.5 (3) |
C13—C12—C11 | 120.6 (3) | C51—C52—C53 | 121.5 (3) |
C13—C12—H12 | 119.7 | C51—C52—H52 | 119.2 |
C11—C12—H12 | 119.7 | C53—C52—H52 | 119.2 |
C8—C13—C12 | 120.3 (3) | C52—C53—C48 | 120.0 (3) |
C8—C13—H13 | 119.9 | C52—C53—H53 | 120.0 |
C12—C13—H13 | 119.9 | C48—C53—H53 | 120.0 |
O5—C14—O4 | 119.5 (2) | O45—C54—O44 | 120.3 (3) |
O5—C14—C15 | 122.5 (2) | O45—C54—C55 | 122.1 (3) |
O4—C14—C15 | 118.0 (2) | O44—C54—C55 | 117.7 (2) |
C20—C15—C16 | 118.7 (2) | C60—C55—C56 | 118.8 (3) |
C20—C15—C14 | 120.6 (2) | C60—C55—C54 | 120.4 (3) |
C16—C15—C14 | 120.8 (2) | C56—C55—C54 | 120.7 (2) |
O6—C16—C17 | 117.9 (2) | O46—C56—C57 | 118.2 (3) |
O6—C16—C15 | 122.4 (2) | O46—C56—C55 | 122.3 (3) |
C17—C16—C15 | 119.6 (3) | C57—C56—C55 | 119.5 (3) |
C18—C17—C16 | 120.7 (3) | C58—C57—C56 | 120.7 (3) |
C18—C17—H17 | 119.6 | C58—C57—H57 | 119.6 |
C16—C17—H17 | 119.6 | C56—C57—H57 | 119.6 |
C17—C18—C19 | 120.5 (3) | C57—C58—C59 | 120.4 (3) |
C17—C18—H18 | 119.7 | C57—C58—H58 | 119.8 |
C19—C18—H18 | 119.7 | C59—C58—H58 | 119.8 |
C20—C19—C18 | 119.0 (3) | C60—C59—C58 | 118.8 (3) |
C20—C19—N3 | 116.3 (2) | C60—C59—N43 | 116.3 (2) |
C18—C19—N3 | 124.7 (2) | C58—C59—N43 | 124.9 (3) |
C19—C20—C15 | 121.4 (2) | C59—C60—C55 | 121.6 (3) |
C19—C20—H20 | 119.3 | C59—C60—H60 | 119.2 |
C15—C20—H20 | 119.3 | C55—C60—H60 | 119.2 |
C22—C21—C26 | 119.2 (3) | C66—C61—C62 | 119.7 (3) |
C22—C21—N4 | 125.4 (2) | C66—C61—N44 | 115.8 (3) |
C26—C21—N4 | 115.4 (2) | C62—C61—N44 | 124.6 (3) |
C21—C22—C23 | 120.2 (3) | C63—C62—C61 | 119.8 (3) |
C21—C22—H22 | 119.9 | C63—C62—H62 | 120.1 |
C23—C22—H22 | 119.9 | C61—C62—H62 | 120.1 |
C22—C23—C24 | 121.4 (3) | C62—C63—C64 | 121.6 (3) |
C22—C23—H23 | 119.3 | C62—C63—H63 | 119.2 |
C24—C23—H23 | 119.3 | C64—C63—H63 | 119.2 |
C25—C24—C23 | 117.9 (3) | C65—C64—C63 | 117.8 (3) |
C25—C24—C28 | 121.7 (3) | C65—C64—C68 | 121.0 (3) |
C23—C24—C28 | 120.4 (3) | C63—C64—C68 | 121.2 (3) |
C24—C25—C26 | 121.2 (3) | C64—C65—C66 | 121.3 (3) |
C24—C25—H25 | 119.4 | C64—C65—H65 | 119.3 |
C26—C25—H25 | 119.4 | C66—C65—H65 | 119.3 |
C21—C26—C25 | 120.1 (3) | C61—C66—C65 | 119.8 (3) |
C21—C26—H26 | 119.9 | C61—C66—H66 | 120.1 |
C25—C26—H26 | 119.9 | C65—C66—H66 | 120.1 |
C11—C27—H271 | 109.5 | C51—C67—H671 | 109.5 |
C11—C27—H272 | 109.5 | C51—C67—H672 | 109.5 |
H271—C27—H272 | 109.5 | H671—C67—H672 | 109.5 |
C11—C27—H273 | 109.5 | C51—C67—H673 | 109.5 |
H271—C27—H273 | 109.5 | H671—C67—H673 | 109.5 |
H272—C27—H273 | 109.5 | H672—C67—H673 | 109.5 |
C24—C28—H281 | 109.5 | C64—C68—H681 | 109.5 |
C24—C28—H282 | 109.5 | C64—C68—H682 | 109.5 |
H281—C28—H282 | 109.5 | H681—C68—H682 | 109.5 |
C24—C28—H283 | 109.5 | C64—C68—H683 | 109.5 |
H281—C28—H283 | 109.5 | H681—C68—H683 | 109.5 |
H282—C28—H283 | 109.5 | H682—C68—H683 | 109.5 |
Sn1—C29—H291 | 109.5 | Sn2—C69—H691 | 109.5 |
Sn1—C29—H292 | 109.5 | Sn2—C69—H692 | 109.5 |
H291—C29—H292 | 109.5 | H691—C69—H692 | 109.5 |
Sn1—C29—H293 | 109.5 | Sn2—C69—H693 | 109.5 |
H291—C29—H293 | 109.5 | H691—C69—H693 | 109.5 |
H292—C29—H293 | 109.5 | H692—C69—H693 | 109.5 |
Sn1—C30—H301 | 109.5 | Sn2—C70—H701 | 109.5 |
Sn1—C30—H302 | 109.5 | Sn2—C70—H702 | 109.5 |
H301—C30—H302 | 109.5 | H701—C70—H702 | 109.5 |
Sn1—C30—H303 | 109.5 | Sn2—C70—H703 | 109.5 |
H301—C30—H303 | 109.5 | H701—C70—H703 | 109.5 |
H302—C30—H303 | 109.5 | H702—C70—H703 | 109.5 |
| | | |
C6—N1—N2—C8 | 179.6 (2) | C46—N41—N42—C48 | 179.2 (2) |
C19—N3—N4—C21 | 178.0 (2) | C59—N43—N44—C61 | 177.4 (2) |
Sn1—O2—C1—O1 | 2.1 (2) | Sn2—O42—C41—O41 | −5.3 (2) |
Sn1—O2—C1—C2 | −176.6 (3) | Sn2—O42—C41—C42 | 172.6 (3) |
Sn1—O1—C1—O2 | −2.7 (3) | Sn2—O41—C41—O42 | 6.6 (3) |
Sn1—O1—C1—C2 | 176.1 (2) | Sn2—O41—C41—C42 | −171.4 (2) |
O2—C1—C2—C7 | 178.5 (3) | O42—C41—C42—C47 | −174.7 (3) |
O1—C1—C2—C7 | −0.2 (4) | O41—C41—C42—C47 | 3.1 (4) |
O2—C1—C2—C3 | 0.1 (4) | O42—C41—C42—C43 | 3.7 (4) |
O1—C1—C2—C3 | −178.6 (3) | O41—C41—C42—C43 | −178.4 (2) |
C7—C2—C3—O3 | −178.6 (3) | C47—C42—C43—O43 | −179.2 (3) |
C1—C2—C3—O3 | −0.3 (4) | C41—C42—C43—O43 | 2.3 (4) |
C7—C2—C3—C4 | −0.5 (4) | C47—C42—C43—C44 | 0.5 (4) |
C1—C2—C3—C4 | 177.9 (3) | C41—C42—C43—C44 | −177.9 (3) |
O3—C3—C4—C5 | 179.3 (3) | O43—C43—C44—C45 | 179.1 (3) |
C2—C3—C4—C5 | 1.0 (4) | C42—C43—C44—C45 | −0.7 (4) |
C3—C4—C5—C6 | −0.4 (4) | C43—C44—C45—C46 | 0.6 (4) |
C4—C5—C6—C7 | −0.7 (4) | C44—C45—C46—C47 | −0.3 (4) |
C4—C5—C6—N1 | −179.6 (3) | C44—C45—C46—N41 | 179.5 (3) |
N2—N1—C6—C7 | 173.6 (2) | N42—N41—C46—C47 | 172.7 (2) |
N2—N1—C6—C5 | −7.5 (4) | N42—N41—C46—C45 | −7.2 (4) |
C5—C6—C7—C2 | 1.3 (4) | C45—C46—C47—C42 | 0.2 (4) |
N1—C6—C7—C2 | −179.7 (3) | N41—C46—C47—C42 | −179.7 (2) |
C3—C2—C7—C6 | −0.7 (4) | C43—C42—C47—C46 | −0.3 (4) |
C1—C2—C7—C6 | −179.0 (3) | C41—C42—C47—C46 | 178.2 (3) |
N1—N2—C8—C13 | 176.6 (3) | N41—N42—C48—C53 | −175.5 (2) |
N1—N2—C8—C9 | −4.6 (4) | N41—N42—C48—C49 | 5.3 (4) |
C13—C8—C9—C10 | −2.4 (5) | C53—C48—C49—C50 | 1.8 (4) |
N2—C8—C9—C10 | 178.8 (3) | N42—C48—C49—C50 | −179.0 (3) |
C8—C9—C10—C11 | 0.9 (5) | C48—C49—C50—C51 | −0.1 (5) |
C9—C10—C11—C12 | 0.9 (5) | C49—C50—C51—C52 | −0.6 (5) |
C9—C10—C11—C27 | −179.3 (3) | C49—C50—C51—C67 | 178.1 (3) |
C10—C11—C12—C13 | −1.2 (5) | C50—C51—C52—C53 | −0.5 (4) |
C27—C11—C12—C13 | 179.0 (3) | C67—C51—C52—C53 | −179.2 (3) |
C9—C8—C13—C12 | 2.1 (5) | C51—C52—C53—C48 | 2.3 (4) |
N2—C8—C13—C12 | −179.0 (3) | C49—C48—C53—C52 | −2.9 (4) |
C11—C12—C13—C8 | −0.3 (5) | N42—C48—C53—C52 | 177.8 (3) |
Sn1—O5—C14—O4 | −2.5 (2) | Sn2—O45—C54—O44 | −0.8 (2) |
Sn1—O5—C14—C15 | 176.8 (3) | Sn2—O45—C54—C55 | 178.9 (3) |
Sn1—O4—C14—O5 | 3.3 (3) | Sn2—O44—C54—O45 | 1.1 (3) |
Sn1—O4—C14—C15 | −176.1 (2) | Sn2—O44—C54—C55 | −178.6 (2) |
O5—C14—C15—C20 | −175.0 (3) | O45—C54—C55—C60 | 175.8 (3) |
O4—C14—C15—C20 | 4.4 (4) | O44—C54—C55—C60 | −4.5 (4) |
O5—C14—C15—C16 | 5.8 (4) | O45—C54—C55—C56 | −5.5 (4) |
O4—C14—C15—C16 | −174.8 (3) | O44—C54—C55—C56 | 174.2 (2) |
C20—C15—C16—O6 | −178.3 (3) | C60—C55—C56—O46 | −178.9 (3) |
C14—C15—C16—O6 | 1.0 (4) | C54—C55—C56—O46 | 2.5 (4) |
C20—C15—C16—C17 | 1.1 (4) | C60—C55—C56—C57 | 2.6 (4) |
C14—C15—C16—C17 | −179.6 (3) | C54—C55—C56—C57 | −176.1 (3) |
O6—C16—C17—C18 | 178.7 (3) | O46—C56—C57—C58 | 178.8 (3) |
C15—C16—C17—C18 | −0.7 (4) | C55—C56—C57—C58 | −2.6 (4) |
C16—C17—C18—C19 | 0.5 (4) | C56—C57—C58—C59 | 0.5 (4) |
C17—C18—C19—C20 | −0.9 (4) | C57—C58—C59—C60 | 1.7 (4) |
C17—C18—C19—N3 | −178.4 (3) | C57—C58—C59—N43 | −177.7 (3) |
N4—N3—C19—C20 | 168.4 (3) | N44—N43—C59—C60 | 175.9 (2) |
N4—N3—C19—C18 | −14.0 (4) | N44—N43—C59—C58 | −4.6 (4) |
C18—C19—C20—C15 | 1.4 (4) | C58—C59—C60—C55 | −1.7 (4) |
N3—C19—C20—C15 | 179.1 (2) | N43—C59—C60—C55 | 177.7 (2) |
C16—C15—C20—C19 | −1.5 (4) | C56—C55—C60—C59 | −0.4 (4) |
C14—C15—C20—C19 | 179.2 (3) | C54—C55—C60—C59 | 178.3 (3) |
N3—N4—C21—C22 | −9.6 (4) | N43—N44—C61—C66 | 166.8 (3) |
N3—N4—C21—C26 | 172.1 (3) | N43—N44—C61—C62 | −14.1 (4) |
C26—C21—C22—C23 | 0.1 (5) | C66—C61—C62—C63 | −1.2 (4) |
N4—C21—C22—C23 | −178.2 (3) | N44—C61—C62—C63 | 179.7 (3) |
C21—C22—C23—C24 | 0.1 (5) | C61—C62—C63—C64 | −0.1 (5) |
C22—C23—C24—C25 | 0.1 (5) | C62—C63—C64—C65 | 1.7 (5) |
C22—C23—C24—C28 | −180.0 (3) | C62—C63—C64—C68 | −178.3 (3) |
C23—C24—C25—C26 | −0.3 (5) | C63—C64—C65—C66 | −1.9 (5) |
C28—C24—C25—C26 | 179.7 (3) | C68—C64—C65—C66 | 178.1 (3) |
C22—C21—C26—C25 | −0.4 (5) | C62—C61—C66—C65 | 1.0 (5) |
N4—C21—C26—C25 | 178.1 (3) | N44—C61—C66—C65 | −179.9 (3) |
C24—C25—C26—C21 | 0.5 (5) | C64—C65—C66—C61 | 0.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.80 (4) | 1.89 (4) | 2.611 (3) | 150 (4) |
O6—H6···O5 | 0.75 (3) | 2.00 (3) | 2.634 (3) | 142 (4) |
O6—H6···O42 | 0.75 (3) | 2.35 (3) | 2.887 (3) | 130 (3) |
O43—H43···O5 | 0.72 (3) | 2.62 (3) | 3.151 (3) | 132 (3) |
O43—H43···O42 | 0.72 (3) | 2.01 (3) | 2.642 (3) | 146 (4) |
O46—H46···O45 | 0.84 (3) | 1.89 (3) | 2.618 (3) | 145 (3) |
C29—H292···O43 | 0.98 | 2.37 | 3.314 (4) | 162 |
C30—H303···O46i | 0.98 | 2.58 | 3.357 (4) | 136 |
C68—H681···O44ii | 0.98 | 2.56 | 3.463 (4) | 153 |
C69—H691···O2iii | 0.98 | 2.55 | 3.443 (4) | 151 |
C12—H12···Cg7iv | 0.95 | 3.00 | 3.833 (3) | 147 |
C68—H683···Cg5v | 0.98 | 2.86 | 3.625 (3) | 136 |
Symmetry codes: (i) x+1, y, z; (ii) −x−2, −y−1, −z; (iii) x−1, y, z; (iv) −x, −y+1, −z+1; (v) x−1, y−1, z. |
(II) Di-
n-butylbis{2-hydroxy-5-[(
E)-2-(4-methylphenyl)diazen-1-yl]benzoato}tin(IV) benzene hemisolvate
top
Crystal data top
[Sn(C4H9)2(C14H11N2O3)2]·0.5C6H6 | F(000) = 1612 |
Mr = 1564.92 | Dx = 1.447 Mg m−3 |
Triclinic, P1 | Melting point: 448 K |
a = 12.0462 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.6264 (2) Å | Cell parameters from 87809 reflections |
c = 22.8143 (3) Å | θ = 2.0–27.5° |
α = 102.2665 (6)° | µ = 0.76 mm−1 |
β = 100.3180 (6)° | T = 160 K |
γ = 91.6029 (6)° | Prism, orange |
V = 3591.71 (8) Å3 | 0.23 × 0.18 × 0.18 mm |
Z = 2 | |
Data collection top
Nonius KappaCCD diffractometer | 16442 independent reflections |
Radiation source: Nonius FR590 sealed tube generator | 10227 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.083 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
φ and ω scans with κ offsets | h = −15→15 |
Absorption correction: multi-scan (Blessing, 1995) | k = −17→17 |
Tmin = 0.802, Tmax = 0.881 | l = −29→29 |
76914 measured reflections | |
Refinement top
Refinement on F2 | 181 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0557P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
16442 reflections | Δρmax = 1.58 e Å−3 |
971 parameters | Δρmin = −0.95 e Å−3 |
Special details top
Experimental. Solvent used: benzene
Cooling Device: Oxford Cryosystems Cryostream 700
Crystal mount: glued on a glass fibre
Mosaicity (deg.): 0.725 (1)
Frames collected: 540
Seconds exposure per frame: 14
Degrees rotation per frame: 1.4
Crystal-Detector distance (mm): 34.0 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. In each independent molecule of the Sn complex in the structure of (II), the
outer three C-atoms of one n-butyl group are disordered over two conformations.
Refinement of the site occupation factors for the two orientations yielded
values of 0.718 (6) and 0.541 (5) for the major conformation of molecules A
(containing atom Sn1) and B (containing atom Sn2), respectively. Similarity
restraints were applied to the chemically equivalent bond lengths and angles
of all C-atoms in the n-butyl groups, including those of the ordered group in
molecule A. In this way, the well defined geometry of the ordered n-butyl
group helped to maintain reasonable geometry within the two conformations of
the disordered ligands. The length of the first n-butyl C—C bond out from
the Sn atom was also restrained to 1.520 (5) Å. Neighbouring C atoms within
and between each conformation of the disordered n-butyl groups were restrained
to have similar atomic displacement parameters. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Sn1 | 0.44920 (2) | 0.59909 (2) | 0.09762 (2) | 0.03200 (8) | |
O1 | 0.33833 (19) | 0.50947 (16) | 0.02250 (10) | 0.0353 (6) | |
O2 | 0.2592 (2) | 0.65266 (16) | 0.04583 (11) | 0.0388 (6) | |
O3 | 0.0608 (2) | 0.67716 (17) | −0.01607 (12) | 0.0443 (6) | |
H3 | 0.1191 | 0.6934 | 0.0112 | 0.066* | |
O4 | 0.5435 (2) | 0.47234 (16) | 0.08918 (11) | 0.0366 (6) | |
O5 | 0.6404 (2) | 0.58034 (17) | 0.16900 (11) | 0.0407 (6) | |
O6 | 0.8167 (2) | 0.52092 (17) | 0.23536 (12) | 0.0449 (6) | |
H6 | 0.7713 | 0.5622 | 0.2244 | 0.067* | |
N1 | 0.0642 (2) | 0.2813 (2) | −0.14326 (13) | 0.0339 (7) | |
N2 | −0.0197 (2) | 0.2482 (2) | −0.18465 (13) | 0.0341 (7) | |
N3 | 0.7190 (3) | 0.1484 (2) | 0.07225 (14) | 0.0388 (7) | |
N4 | 0.7796 (3) | 0.0789 (2) | 0.08239 (14) | 0.0422 (8) | |
C1 | 0.2547 (3) | 0.5647 (2) | 0.01351 (15) | 0.0331 (8) | |
C2 | 0.1560 (3) | 0.5229 (2) | −0.03385 (15) | 0.0280 (8) | |
C3 | 0.0640 (3) | 0.5815 (2) | −0.04607 (16) | 0.0342 (8) | |
C4 | −0.0290 (3) | 0.5392 (3) | −0.09142 (17) | 0.0407 (9) | |
H4 | −0.0911 | 0.5787 | −0.1001 | 0.049* | |
C5 | −0.0321 (3) | 0.4414 (3) | −0.12360 (16) | 0.0358 (8) | |
H5 | −0.0965 | 0.4135 | −0.1539 | 0.043* | |
C6 | 0.0595 (3) | 0.3827 (2) | −0.11182 (15) | 0.0304 (8) | |
C7 | 0.1516 (3) | 0.4234 (2) | −0.06746 (15) | 0.0294 (8) | |
H7 | 0.2135 | 0.3835 | −0.0594 | 0.035* | |
C8 | −0.0168 (3) | 0.1460 (2) | −0.21532 (15) | 0.0316 (8) | |
C9 | 0.0705 (3) | 0.0847 (3) | −0.20264 (16) | 0.0389 (9) | |
H9 | 0.1349 | 0.1106 | −0.1719 | 0.047* | |
C10 | 0.0632 (3) | −0.0138 (3) | −0.23479 (17) | 0.0420 (9) | |
H10 | 0.1233 | −0.0553 | −0.2260 | 0.050* | |
C11 | −0.0298 (3) | −0.0535 (3) | −0.27958 (17) | 0.0405 (9) | |
C12 | −0.1157 (3) | 0.0084 (3) | −0.29292 (17) | 0.0455 (10) | |
H12 | −0.1795 | −0.0172 | −0.3241 | 0.055* | |
C13 | −0.1088 (3) | 0.1083 (3) | −0.26073 (16) | 0.0408 (9) | |
H13 | −0.1678 | 0.1504 | −0.2702 | 0.049* | |
C14 | 0.6276 (3) | 0.4939 (2) | 0.13494 (16) | 0.0320 (8) | |
C15 | 0.7035 (3) | 0.4144 (2) | 0.14517 (15) | 0.0307 (8) | |
C16 | 0.7921 (3) | 0.4304 (2) | 0.19580 (16) | 0.0332 (8) | |
C17 | 0.8572 (3) | 0.3515 (3) | 0.20698 (17) | 0.0397 (9) | |
H17 | 0.9159 | 0.3619 | 0.2420 | 0.048* | |
C18 | 0.8375 (3) | 0.2579 (3) | 0.16750 (17) | 0.0401 (9) | |
H18 | 0.8833 | 0.2047 | 0.1751 | 0.048* | |
C19 | 0.7500 (3) | 0.2417 (2) | 0.11650 (16) | 0.0330 (8) | |
C20 | 0.6835 (3) | 0.3192 (2) | 0.10639 (16) | 0.0330 (8) | |
H20 | 0.6227 | 0.3075 | 0.0723 | 0.040* | |
C21 | 0.7465 (3) | −0.0141 (3) | 0.03794 (16) | 0.0359 (9) | |
C22 | 0.6494 (3) | −0.0296 (3) | −0.00670 (18) | 0.0455 (10) | |
H22 | 0.6004 | 0.0232 | −0.0100 | 0.055* | |
C23 | 0.6240 (3) | −0.1234 (3) | −0.04675 (17) | 0.0438 (9) | |
H23 | 0.5571 | −0.1344 | −0.0772 | 0.053* | |
C24 | 0.6955 (3) | −0.2008 (3) | −0.04261 (17) | 0.0377 (9) | |
C25 | 0.7919 (3) | −0.1834 (3) | 0.00258 (17) | 0.0447 (10) | |
H25 | 0.8416 | −0.2357 | 0.0059 | 0.054* | |
C26 | 0.8166 (3) | −0.0916 (3) | 0.04264 (17) | 0.0448 (10) | |
H26 | 0.8824 | −0.0814 | 0.0738 | 0.054* | |
C27 | −0.0388 (4) | −0.1633 (3) | −0.31433 (19) | 0.0546 (12) | |
H271 | 0.0365 | −0.1894 | −0.3104 | 0.082* | |
H272 | −0.0702 | −0.1677 | −0.3576 | 0.082* | |
H273 | −0.0885 | −0.2033 | −0.2973 | 0.082* | |
C28 | 0.6685 (3) | −0.3021 (3) | −0.08653 (18) | 0.0496 (11) | |
H281 | 0.5883 | −0.3226 | −0.0911 | 0.074* | |
H282 | 0.7148 | −0.3521 | −0.0706 | 0.074* | |
H283 | 0.6851 | −0.2972 | −0.1264 | 0.074* | |
C29 | 0.3650 (3) | 0.5830 (3) | 0.16937 (17) | 0.0433 (10) | |
H291 | 0.2900 | 0.5475 | 0.1509 | 0.052* | |
H292 | 0.4085 | 0.5390 | 0.1931 | 0.052* | |
C30 | 0.3475 (4) | 0.6780 (3) | 0.21331 (18) | 0.0596 (12) | |
H301 | 0.2900 | 0.6638 | 0.2370 | 0.072* | |
H302 | 0.3190 | 0.7289 | 0.1902 | 0.072* | |
C31 | 0.4590 (4) | 0.7200 (4) | 0.2574 (2) | 0.0743 (15) | |
H311 | 0.4858 | 0.6697 | 0.2813 | 0.089* | |
H312 | 0.5171 | 0.7314 | 0.2334 | 0.089* | |
C32 | 0.4460 (4) | 0.8152 (4) | 0.2996 (2) | 0.0817 (16) | |
H321 | 0.4185 | 0.8650 | 0.2762 | 0.123* | |
H322 | 0.5192 | 0.8403 | 0.3259 | 0.123* | |
H323 | 0.3915 | 0.8035 | 0.3250 | 0.123* | |
C33 | 0.5362 (3) | 0.7035 (2) | 0.06225 (16) | 0.0410 (9) | |
H331 | 0.5954 | 0.6681 | 0.0427 | 0.049* | 0.718 (6) |
H332 | 0.4820 | 0.7239 | 0.0297 | 0.049* | 0.718 (6) |
H333 | 0.6174 | 0.7067 | 0.0810 | 0.049* | 0.282 (6) |
H334 | 0.5298 | 0.6762 | 0.0179 | 0.049* | 0.282 (6) |
C34A | 0.5916 (5) | 0.7974 (3) | 0.1063 (2) | 0.0485 (15) | 0.718 (6) |
H341 | 0.6410 | 0.8321 | 0.0856 | 0.058* | 0.718 (6) |
H342 | 0.6405 | 0.7778 | 0.1411 | 0.058* | 0.718 (6) |
C35A | 0.5106 (6) | 0.8710 (7) | 0.1310 (4) | 0.067 (2) | 0.718 (6) |
H351 | 0.4603 | 0.8899 | 0.0964 | 0.081* | 0.718 (6) |
H352 | 0.4628 | 0.8377 | 0.1532 | 0.081* | 0.718 (6) |
C36A | 0.5708 (7) | 0.9646 (5) | 0.1734 (3) | 0.079 (2) | 0.718 (6) |
H361 | 0.5153 | 1.0076 | 0.1905 | 0.118* | 0.718 (6) |
H362 | 0.6127 | 1.0012 | 0.1506 | 0.118* | 0.718 (6) |
H363 | 0.6236 | 0.9461 | 0.2066 | 0.118* | 0.718 (6) |
C34B | 0.4994 (11) | 0.8094 (5) | 0.0710 (6) | 0.044 (2) | 0.282 (6) |
H343 | 0.4259 | 0.8088 | 0.0433 | 0.053* | 0.282 (6) |
H344 | 0.5550 | 0.8513 | 0.0582 | 0.053* | 0.282 (6) |
C35B | 0.4865 (14) | 0.860 (2) | 0.1356 (8) | 0.061 (4) | 0.282 (6) |
H353 | 0.4361 | 0.9160 | 0.1338 | 0.073* | 0.282 (6) |
H354 | 0.4512 | 0.8109 | 0.1541 | 0.073* | 0.282 (6) |
C36B | 0.5992 (16) | 0.9004 (17) | 0.1745 (7) | 0.089 (5) | 0.282 (6) |
H364 | 0.6416 | 0.9367 | 0.1519 | 0.134* | 0.282 (6) |
H365 | 0.6418 | 0.8444 | 0.1851 | 0.134* | 0.282 (6) |
H366 | 0.5877 | 0.9463 | 0.2120 | 0.134* | 0.282 (6) |
Sn2 | 0.59619 (2) | 0.66771 (2) | 0.49220 (2) | 0.02954 (8) | |
O41 | 0.6835 (2) | 0.53667 (16) | 0.48649 (11) | 0.0362 (6) | |
O42 | 0.79209 (19) | 0.64877 (15) | 0.55971 (10) | 0.0342 (5) | |
O43 | 0.9810 (2) | 0.59333 (17) | 0.61777 (11) | 0.0403 (6) | |
H43 | 0.9320 | 0.6335 | 0.6094 | 0.061* | |
O44 | 0.48199 (19) | 0.57754 (16) | 0.41943 (11) | 0.0387 (6) | |
O45 | 0.40301 (19) | 0.72170 (16) | 0.43866 (10) | 0.0346 (6) | |
O46 | 0.2034 (2) | 0.74147 (16) | 0.37532 (11) | 0.0370 (6) | |
H46 | 0.2549 | 0.7557 | 0.4065 | 0.056* | |
N41 | 0.8703 (2) | 0.2176 (2) | 0.46087 (13) | 0.0333 (7) | |
N42 | 0.9407 (2) | 0.1516 (2) | 0.46245 (13) | 0.0339 (7) | |
N43 | 0.2245 (3) | 0.3468 (2) | 0.24958 (13) | 0.0376 (7) | |
N44 | 0.1498 (2) | 0.3132 (2) | 0.20366 (13) | 0.0336 (7) | |
C41 | 0.7749 (3) | 0.5608 (2) | 0.52757 (15) | 0.0288 (8) | |
C42 | 0.8542 (3) | 0.4826 (2) | 0.53486 (15) | 0.0272 (7) | |
C43 | 0.9531 (3) | 0.5030 (2) | 0.57958 (16) | 0.0310 (8) | |
C44 | 1.0267 (3) | 0.4255 (2) | 0.58553 (17) | 0.0372 (9) | |
H44 | 1.0934 | 0.4380 | 0.6161 | 0.045* | |
C45 | 1.0024 (3) | 0.3323 (3) | 0.54739 (16) | 0.0345 (8) | |
H45 | 1.0530 | 0.2809 | 0.5516 | 0.041* | |
C46 | 0.9052 (3) | 0.3117 (2) | 0.50278 (15) | 0.0296 (8) | |
C47 | 0.8311 (3) | 0.3864 (2) | 0.49697 (15) | 0.0279 (7) | |
H47 | 0.7638 | 0.3722 | 0.4669 | 0.033* | |
C48 | 0.9028 (3) | 0.0582 (2) | 0.42035 (16) | 0.0322 (8) | |
C49 | 0.7972 (3) | 0.0381 (3) | 0.38221 (17) | 0.0373 (9) | |
H49 | 0.7443 | 0.0886 | 0.3827 | 0.045* | |
C50 | 0.7699 (3) | −0.0548 (3) | 0.34394 (17) | 0.0396 (9) | |
H50 | 0.6976 | −0.0680 | 0.3181 | 0.048* | |
C51 | 0.8457 (3) | −0.1309 (3) | 0.34199 (17) | 0.0394 (9) | |
C52 | 0.9500 (3) | −0.1095 (2) | 0.37948 (17) | 0.0382 (9) | |
H52 | 1.0031 | −0.1598 | 0.3784 | 0.046* | |
C53 | 0.9797 (3) | −0.0162 (2) | 0.41902 (16) | 0.0353 (8) | |
H53 | 1.0520 | −0.0032 | 0.4449 | 0.042* | |
C54 | 0.3990 (3) | 0.6328 (2) | 0.40817 (15) | 0.0298 (8) | |
C55 | 0.3032 (3) | 0.5893 (2) | 0.35965 (15) | 0.0283 (7) | |
C56 | 0.2098 (3) | 0.6457 (2) | 0.34531 (15) | 0.0282 (8) | |
C57 | 0.1204 (3) | 0.6022 (2) | 0.29813 (15) | 0.0322 (8) | |
H57 | 0.0573 | 0.6402 | 0.2887 | 0.039* | |
C58 | 0.1218 (3) | 0.5055 (2) | 0.26506 (15) | 0.0320 (8) | |
H58 | 0.0607 | 0.4773 | 0.2327 | 0.038* | |
C59 | 0.2141 (3) | 0.4491 (2) | 0.27952 (15) | 0.0305 (8) | |
C60 | 0.3028 (3) | 0.4905 (2) | 0.32604 (15) | 0.0327 (8) | |
H60 | 0.3648 | 0.4514 | 0.3355 | 0.039* | |
C61 | 0.1580 (3) | 0.2091 (2) | 0.17527 (15) | 0.0323 (8) | |
C62 | 0.2366 (3) | 0.1480 (3) | 0.19879 (17) | 0.0424 (9) | |
H62 | 0.2908 | 0.1742 | 0.2349 | 0.051* | |
C63 | 0.2345 (3) | 0.0484 (3) | 0.16858 (17) | 0.0458 (10) | |
H63 | 0.2873 | 0.0062 | 0.1850 | 0.055* | |
C64 | 0.1587 (3) | 0.0082 (3) | 0.11554 (17) | 0.0412 (10) | |
C65 | 0.0818 (3) | 0.0715 (3) | 0.09272 (17) | 0.0421 (9) | |
H65 | 0.0284 | 0.0456 | 0.0562 | 0.051* | |
C66 | 0.0816 (3) | 0.1710 (3) | 0.12207 (16) | 0.0392 (9) | |
H66 | 0.0288 | 0.2131 | 0.1056 | 0.047* | |
C67 | 0.8131 (3) | −0.2332 (3) | 0.29954 (17) | 0.0456 (10) | |
H671 | 0.7388 | −0.2580 | 0.3043 | 0.068* | |
H672 | 0.8695 | −0.2804 | 0.3097 | 0.068* | |
H673 | 0.8099 | −0.2273 | 0.2572 | 0.068* | |
C68 | 0.1583 (4) | −0.1011 (3) | 0.08387 (18) | 0.0505 (11) | |
H681 | 0.0941 | −0.1178 | 0.0495 | 0.076* | |
H682 | 0.1515 | −0.1437 | 0.1129 | 0.076* | |
H683 | 0.2290 | −0.1128 | 0.0687 | 0.076* | |
C69 | 0.6876 (3) | 0.7558 (2) | 0.44813 (16) | 0.0354 (8) | |
H691 | 0.7516 | 0.7179 | 0.4357 | 0.042* | |
H692 | 0.6374 | 0.7645 | 0.4105 | 0.042* | |
C70 | 0.7342 (3) | 0.8596 (2) | 0.48601 (17) | 0.0377 (9) | |
H701 | 0.7735 | 0.8529 | 0.5268 | 0.045* | |
H702 | 0.7905 | 0.8872 | 0.4660 | 0.045* | |
C71 | 0.6423 (3) | 0.9328 (3) | 0.49370 (18) | 0.0428 (10) | |
H711 | 0.6045 | 0.9410 | 0.4529 | 0.051* | |
H712 | 0.5849 | 0.9043 | 0.5126 | 0.051* | |
C72 | 0.6880 (3) | 1.0353 (3) | 0.53290 (19) | 0.0496 (11) | |
H721 | 0.7248 | 1.0277 | 0.5735 | 0.074* | |
H722 | 0.6255 | 1.0793 | 0.5368 | 0.074* | |
H723 | 0.7431 | 1.0649 | 0.5137 | 0.074* | |
C73 | 0.5172 (3) | 0.6722 (3) | 0.56841 (16) | 0.0406 (9) | |
H731 | 0.4405 | 0.6957 | 0.5587 | 0.049* | 0.459 (5) |
H732 | 0.5084 | 0.6027 | 0.5744 | 0.049* | 0.459 (5) |
H733 | 0.4488 | 0.6251 | 0.5556 | 0.049* | 0.541 (5) |
H734 | 0.5695 | 0.6478 | 0.6001 | 0.049* | 0.541 (5) |
C74A | 0.5793 (6) | 0.7393 (4) | 0.6286 (3) | 0.0426 (18) | 0.459 (5) |
H741 | 0.5328 | 0.7367 | 0.6600 | 0.051* | 0.459 (5) |
H742 | 0.6510 | 0.7090 | 0.6410 | 0.051* | 0.459 (5) |
C75A | 0.6075 (8) | 0.8498 (6) | 0.6303 (10) | 0.045 (3) | 0.459 (5) |
H751 | 0.6551 | 0.8815 | 0.6703 | 0.055* | 0.459 (5) |
H752 | 0.6516 | 0.8544 | 0.5982 | 0.055* | 0.459 (5) |
C76A | 0.5026 (8) | 0.9061 (6) | 0.6205 (5) | 0.056 (3) | 0.459 (5) |
H761 | 0.4583 | 0.9010 | 0.6520 | 0.084* | 0.459 (5) |
H762 | 0.4572 | 0.8770 | 0.5801 | 0.084* | 0.459 (5) |
H763 | 0.5241 | 0.9771 | 0.6232 | 0.084* | 0.459 (5) |
C74B | 0.4838 (5) | 0.7743 (4) | 0.5961 (3) | 0.0401 (17) | 0.541 (5) |
H743 | 0.4273 | 0.7679 | 0.6219 | 0.048* | 0.541 (5) |
H744 | 0.4499 | 0.8081 | 0.5635 | 0.048* | 0.541 (5) |
C75B | 0.5896 (7) | 0.8355 (6) | 0.6347 (8) | 0.047 (2) | 0.541 (5) |
H753 | 0.6260 | 0.7988 | 0.6653 | 0.056* | 0.541 (5) |
H754 | 0.6440 | 0.8446 | 0.6082 | 0.056* | 0.541 (5) |
C76B | 0.5598 (7) | 0.9374 (5) | 0.6671 (4) | 0.064 (2) | 0.541 (5) |
H764 | 0.6283 | 0.9748 | 0.6928 | 0.097* | 0.541 (5) |
H765 | 0.5047 | 0.9283 | 0.6926 | 0.097* | 0.541 (5) |
H766 | 0.5271 | 0.9750 | 0.6367 | 0.097* | 0.541 (5) |
C80 | 0.5366 (4) | 0.3454 (4) | 0.2498 (2) | 0.0760 (14) | |
H80 | 0.4710 | 0.3621 | 0.2249 | 0.091* | |
C81 | 0.5734 (4) | 0.2499 (4) | 0.2372 (2) | 0.0677 (14) | |
H81 | 0.5328 | 0.2010 | 0.2036 | 0.081* | |
C82 | 0.6672 (4) | 0.2246 (4) | 0.2721 (2) | 0.0676 (13) | |
H82 | 0.6925 | 0.1586 | 0.2634 | 0.081* | |
C83 | 0.7251 (4) | 0.2975 (4) | 0.3207 (2) | 0.0713 (14) | |
H83 | 0.7918 | 0.2819 | 0.3452 | 0.086* | |
C84 | 0.6871 (4) | 0.3912 (4) | 0.3336 (2) | 0.0668 (13) | |
H84 | 0.7262 | 0.4399 | 0.3678 | 0.080* | |
C85 | 0.5940 (5) | 0.4159 (4) | 0.2980 (2) | 0.0698 (14) | |
H85 | 0.5690 | 0.4821 | 0.3067 | 0.084* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.03061 (15) | 0.02481 (14) | 0.03640 (16) | 0.00053 (10) | 0.00358 (12) | 0.00003 (11) |
O1 | 0.0303 (14) | 0.0280 (13) | 0.0403 (14) | 0.0043 (11) | −0.0027 (11) | −0.0006 (11) |
O2 | 0.0418 (15) | 0.0269 (13) | 0.0416 (15) | 0.0031 (11) | 0.0024 (12) | −0.0015 (11) |
O3 | 0.0473 (17) | 0.0305 (14) | 0.0464 (17) | 0.0129 (12) | −0.0012 (13) | −0.0033 (12) |
O4 | 0.0371 (15) | 0.0272 (13) | 0.0403 (15) | 0.0031 (11) | −0.0005 (12) | 0.0027 (11) |
O5 | 0.0386 (15) | 0.0286 (13) | 0.0499 (16) | 0.0048 (11) | 0.0071 (13) | −0.0019 (12) |
O6 | 0.0409 (16) | 0.0276 (14) | 0.0533 (17) | −0.0008 (12) | −0.0076 (13) | −0.0051 (12) |
N1 | 0.0354 (18) | 0.0296 (16) | 0.0348 (17) | −0.0001 (14) | 0.0026 (15) | 0.0063 (13) |
N2 | 0.0372 (18) | 0.0307 (16) | 0.0321 (17) | 0.0008 (14) | 0.0042 (15) | 0.0042 (13) |
N3 | 0.044 (2) | 0.0290 (16) | 0.0454 (19) | 0.0085 (15) | 0.0142 (16) | 0.0081 (14) |
N4 | 0.043 (2) | 0.0366 (18) | 0.045 (2) | 0.0013 (16) | 0.0058 (16) | 0.0085 (15) |
C1 | 0.037 (2) | 0.0274 (19) | 0.035 (2) | 0.0019 (16) | 0.0097 (17) | 0.0052 (16) |
C2 | 0.0279 (19) | 0.0259 (18) | 0.0285 (19) | −0.0008 (15) | 0.0052 (16) | 0.0028 (14) |
C3 | 0.043 (2) | 0.0247 (18) | 0.033 (2) | 0.0093 (17) | 0.0064 (18) | 0.0025 (15) |
C4 | 0.037 (2) | 0.039 (2) | 0.043 (2) | 0.0139 (18) | 0.0005 (19) | 0.0065 (18) |
C5 | 0.033 (2) | 0.037 (2) | 0.033 (2) | 0.0042 (17) | −0.0008 (17) | 0.0041 (16) |
C6 | 0.033 (2) | 0.0244 (18) | 0.0319 (19) | 0.0032 (15) | 0.0048 (17) | 0.0036 (15) |
C7 | 0.0285 (19) | 0.0269 (18) | 0.0312 (19) | 0.0054 (15) | 0.0036 (16) | 0.0045 (15) |
C8 | 0.033 (2) | 0.0302 (19) | 0.030 (2) | −0.0004 (16) | 0.0042 (16) | 0.0047 (16) |
C9 | 0.042 (2) | 0.035 (2) | 0.035 (2) | 0.0017 (18) | −0.0002 (18) | 0.0052 (17) |
C10 | 0.052 (3) | 0.031 (2) | 0.041 (2) | 0.0031 (18) | 0.004 (2) | 0.0064 (17) |
C11 | 0.056 (3) | 0.030 (2) | 0.038 (2) | −0.0021 (19) | 0.017 (2) | 0.0059 (17) |
C12 | 0.046 (3) | 0.042 (2) | 0.039 (2) | −0.0103 (19) | −0.0011 (19) | −0.0017 (18) |
C13 | 0.035 (2) | 0.039 (2) | 0.042 (2) | 0.0038 (17) | 0.0008 (18) | 0.0018 (18) |
C14 | 0.029 (2) | 0.031 (2) | 0.036 (2) | −0.0006 (16) | 0.0081 (17) | 0.0053 (16) |
C15 | 0.031 (2) | 0.0259 (18) | 0.036 (2) | 0.0026 (15) | 0.0115 (17) | 0.0040 (15) |
C16 | 0.030 (2) | 0.0288 (19) | 0.038 (2) | −0.0023 (16) | 0.0062 (17) | 0.0005 (16) |
C17 | 0.029 (2) | 0.038 (2) | 0.048 (2) | −0.0002 (17) | −0.0009 (18) | 0.0087 (18) |
C18 | 0.035 (2) | 0.033 (2) | 0.055 (3) | 0.0099 (17) | 0.012 (2) | 0.0128 (18) |
C19 | 0.039 (2) | 0.0269 (19) | 0.036 (2) | 0.0013 (16) | 0.0150 (18) | 0.0055 (16) |
C20 | 0.035 (2) | 0.032 (2) | 0.031 (2) | 0.0037 (16) | 0.0076 (17) | 0.0039 (16) |
C21 | 0.043 (2) | 0.032 (2) | 0.031 (2) | −0.0079 (17) | 0.0097 (18) | −0.0001 (16) |
C22 | 0.044 (2) | 0.033 (2) | 0.059 (3) | 0.0062 (18) | 0.013 (2) | 0.0063 (19) |
C23 | 0.040 (2) | 0.037 (2) | 0.047 (2) | −0.0037 (18) | 0.0026 (19) | 0.0002 (18) |
C24 | 0.043 (2) | 0.030 (2) | 0.041 (2) | −0.0040 (17) | 0.016 (2) | 0.0051 (17) |
C25 | 0.055 (3) | 0.033 (2) | 0.049 (2) | 0.0076 (19) | 0.015 (2) | 0.0089 (18) |
C26 | 0.053 (3) | 0.038 (2) | 0.044 (2) | 0.0054 (19) | 0.010 (2) | 0.0069 (18) |
C27 | 0.079 (3) | 0.032 (2) | 0.049 (3) | −0.005 (2) | 0.019 (2) | −0.0039 (18) |
C28 | 0.059 (3) | 0.030 (2) | 0.060 (3) | −0.0074 (19) | 0.025 (2) | 0.0007 (19) |
C29 | 0.039 (2) | 0.049 (2) | 0.044 (2) | −0.0017 (18) | 0.0126 (19) | 0.0105 (19) |
C30 | 0.058 (3) | 0.066 (3) | 0.052 (3) | −0.010 (2) | 0.021 (2) | 0.001 (2) |
C31 | 0.060 (3) | 0.092 (4) | 0.066 (3) | −0.011 (3) | 0.018 (3) | 0.002 (3) |
C32 | 0.079 (4) | 0.082 (4) | 0.072 (4) | −0.016 (3) | 0.016 (3) | −0.007 (3) |
C33 | 0.046 (2) | 0.033 (2) | 0.044 (2) | 0.0010 (17) | 0.0121 (19) | 0.0051 (17) |
C34A | 0.054 (3) | 0.037 (3) | 0.056 (3) | −0.004 (2) | 0.019 (3) | 0.006 (2) |
C35A | 0.079 (4) | 0.042 (4) | 0.082 (4) | −0.015 (3) | 0.036 (3) | 0.003 (3) |
C36A | 0.104 (6) | 0.041 (4) | 0.083 (5) | −0.009 (4) | 0.026 (4) | −0.010 (4) |
C34B | 0.057 (5) | 0.028 (4) | 0.055 (5) | 0.002 (4) | 0.030 (4) | 0.007 (4) |
C35B | 0.081 (6) | 0.034 (6) | 0.073 (6) | −0.013 (6) | 0.034 (6) | 0.009 (5) |
C36B | 0.087 (10) | 0.099 (10) | 0.083 (9) | −0.011 (10) | 0.020 (8) | 0.020 (9) |
Sn2 | 0.02860 (14) | 0.01906 (13) | 0.03559 (15) | 0.00263 (10) | −0.00071 (11) | −0.00019 (10) |
O41 | 0.0338 (14) | 0.0254 (12) | 0.0410 (15) | 0.0060 (11) | −0.0068 (12) | −0.0001 (11) |
O42 | 0.0343 (14) | 0.0219 (12) | 0.0403 (14) | 0.0042 (10) | 0.0002 (11) | −0.0010 (11) |
O43 | 0.0337 (15) | 0.0281 (13) | 0.0485 (16) | 0.0023 (11) | −0.0094 (12) | −0.0006 (12) |
O44 | 0.0325 (14) | 0.0234 (12) | 0.0479 (15) | 0.0049 (11) | −0.0122 (12) | −0.0028 (11) |
O45 | 0.0346 (14) | 0.0256 (13) | 0.0384 (14) | 0.0026 (11) | 0.0009 (11) | 0.0006 (11) |
O46 | 0.0342 (15) | 0.0280 (13) | 0.0426 (16) | 0.0082 (11) | −0.0020 (12) | 0.0006 (11) |
N41 | 0.0298 (17) | 0.0266 (16) | 0.0438 (19) | 0.0067 (13) | 0.0069 (14) | 0.0076 (14) |
N42 | 0.0319 (17) | 0.0232 (15) | 0.0467 (19) | 0.0049 (13) | 0.0097 (15) | 0.0056 (13) |
N43 | 0.0372 (19) | 0.0322 (17) | 0.0360 (18) | −0.0025 (14) | −0.0025 (15) | −0.0002 (14) |
N44 | 0.0379 (18) | 0.0282 (16) | 0.0304 (17) | −0.0010 (13) | 0.0030 (14) | −0.0002 (13) |
C41 | 0.030 (2) | 0.0239 (18) | 0.031 (2) | 0.0041 (15) | 0.0042 (16) | 0.0040 (15) |
C42 | 0.0253 (19) | 0.0244 (17) | 0.0302 (19) | 0.0028 (14) | 0.0052 (16) | 0.0027 (14) |
C43 | 0.030 (2) | 0.0251 (18) | 0.035 (2) | −0.0035 (15) | 0.0026 (16) | 0.0038 (15) |
C44 | 0.029 (2) | 0.029 (2) | 0.049 (2) | 0.0002 (16) | −0.0033 (17) | 0.0075 (17) |
C45 | 0.0238 (19) | 0.0311 (19) | 0.050 (2) | 0.0064 (15) | 0.0045 (17) | 0.0131 (17) |
C46 | 0.031 (2) | 0.0243 (18) | 0.035 (2) | 0.0035 (15) | 0.0083 (17) | 0.0079 (15) |
C47 | 0.0271 (19) | 0.0239 (17) | 0.0297 (19) | 0.0045 (14) | 0.0001 (15) | 0.0034 (14) |
C48 | 0.031 (2) | 0.0243 (18) | 0.043 (2) | 0.0029 (15) | 0.0126 (18) | 0.0080 (16) |
C49 | 0.034 (2) | 0.030 (2) | 0.048 (2) | 0.0101 (16) | 0.0073 (19) | 0.0069 (17) |
C50 | 0.039 (2) | 0.031 (2) | 0.046 (2) | 0.0031 (17) | 0.0030 (19) | 0.0058 (17) |
C51 | 0.050 (3) | 0.028 (2) | 0.043 (2) | 0.0016 (18) | 0.020 (2) | 0.0042 (17) |
C52 | 0.038 (2) | 0.0266 (19) | 0.053 (2) | 0.0090 (17) | 0.017 (2) | 0.0053 (17) |
C53 | 0.030 (2) | 0.0298 (19) | 0.046 (2) | 0.0052 (16) | 0.0108 (18) | 0.0058 (17) |
C54 | 0.030 (2) | 0.0244 (18) | 0.033 (2) | 0.0009 (15) | 0.0035 (16) | 0.0037 (15) |
C55 | 0.0294 (19) | 0.0271 (18) | 0.0270 (19) | 0.0018 (15) | 0.0021 (15) | 0.0059 (14) |
C56 | 0.0285 (19) | 0.0251 (18) | 0.0304 (19) | 0.0013 (15) | 0.0080 (16) | 0.0028 (15) |
C57 | 0.0252 (19) | 0.034 (2) | 0.035 (2) | 0.0045 (15) | −0.0024 (16) | 0.0086 (16) |
C58 | 0.0259 (19) | 0.037 (2) | 0.0297 (19) | −0.0030 (16) | −0.0013 (16) | 0.0061 (16) |
C59 | 0.035 (2) | 0.0251 (18) | 0.0287 (19) | −0.0011 (16) | 0.0021 (16) | 0.0033 (15) |
C60 | 0.034 (2) | 0.0235 (18) | 0.036 (2) | 0.0025 (15) | 0.0009 (17) | 0.0016 (15) |
C61 | 0.039 (2) | 0.0294 (19) | 0.0281 (19) | −0.0009 (16) | 0.0081 (17) | 0.0043 (15) |
C62 | 0.049 (3) | 0.039 (2) | 0.033 (2) | −0.0007 (19) | 0.0024 (19) | −0.0007 (17) |
C63 | 0.058 (3) | 0.032 (2) | 0.046 (2) | 0.0095 (19) | 0.008 (2) | 0.0071 (18) |
C64 | 0.051 (3) | 0.033 (2) | 0.039 (2) | −0.0028 (19) | 0.017 (2) | 0.0006 (18) |
C65 | 0.040 (2) | 0.038 (2) | 0.041 (2) | −0.0076 (18) | 0.0074 (19) | −0.0054 (18) |
C66 | 0.034 (2) | 0.040 (2) | 0.037 (2) | −0.0065 (17) | 0.0013 (18) | 0.0018 (17) |
C67 | 0.052 (3) | 0.033 (2) | 0.047 (2) | 0.0013 (19) | 0.013 (2) | −0.0019 (18) |
C68 | 0.066 (3) | 0.030 (2) | 0.050 (3) | −0.0072 (19) | 0.018 (2) | −0.0085 (18) |
C69 | 0.031 (2) | 0.035 (2) | 0.039 (2) | 0.0041 (16) | 0.0084 (17) | 0.0058 (17) |
C70 | 0.032 (2) | 0.034 (2) | 0.047 (2) | −0.0016 (16) | 0.0093 (18) | 0.0071 (17) |
C71 | 0.040 (2) | 0.032 (2) | 0.056 (3) | 0.0004 (17) | 0.007 (2) | 0.0120 (18) |
C72 | 0.046 (3) | 0.030 (2) | 0.070 (3) | 0.0027 (18) | 0.012 (2) | 0.005 (2) |
C73 | 0.040 (2) | 0.038 (2) | 0.046 (2) | −0.0010 (17) | 0.0124 (18) | 0.0115 (17) |
C74A | 0.051 (4) | 0.032 (3) | 0.042 (4) | 0.005 (3) | 0.006 (3) | 0.005 (3) |
C75A | 0.053 (5) | 0.040 (4) | 0.038 (5) | −0.003 (4) | 0.004 (4) | 0.002 (4) |
C76A | 0.054 (6) | 0.048 (5) | 0.066 (6) | 0.016 (4) | 0.007 (5) | 0.018 (5) |
C74B | 0.037 (3) | 0.040 (3) | 0.042 (3) | 0.001 (3) | 0.013 (3) | 0.002 (3) |
C75B | 0.052 (4) | 0.051 (4) | 0.033 (4) | 0.004 (4) | 0.007 (4) | −0.002 (4) |
C76B | 0.071 (6) | 0.052 (5) | 0.056 (5) | −0.003 (4) | 0.006 (5) | −0.014 (4) |
C80 | 0.063 (3) | 0.089 (4) | 0.068 (4) | 0.007 (3) | 0.000 (3) | 0.009 (3) |
C81 | 0.064 (3) | 0.080 (4) | 0.053 (3) | −0.017 (3) | 0.015 (3) | 0.000 (3) |
C82 | 0.069 (4) | 0.077 (3) | 0.061 (3) | 0.008 (3) | 0.025 (3) | 0.014 (3) |
C83 | 0.050 (3) | 0.100 (4) | 0.062 (3) | 0.003 (3) | 0.003 (3) | 0.022 (3) |
C84 | 0.071 (4) | 0.076 (4) | 0.050 (3) | −0.020 (3) | 0.012 (3) | 0.008 (3) |
C85 | 0.076 (4) | 0.068 (3) | 0.065 (3) | 0.000 (3) | 0.021 (3) | 0.008 (3) |
Geometric parameters (Å, º) top
Sn1—O1 | 2.100 (2) | O41—C41 | 1.296 (4) |
Sn1—O2 | 2.581 (2) | O42—C41 | 1.255 (4) |
Sn1—O4 | 2.087 (2) | O43—C43 | 1.343 (4) |
Sn1—O5 | 2.625 (3) | O43—H43 | 0.8400 |
Sn1—C29 | 2.119 (3) | O44—C54 | 1.291 (4) |
Sn1—C33 | 2.117 (3) | O45—C54 | 1.257 (4) |
O1—C1 | 1.287 (4) | O46—C56 | 1.350 (4) |
O2—C1 | 1.261 (4) | O46—H46 | 0.8400 |
O3—C3 | 1.342 (4) | N41—N42 | 1.256 (4) |
O3—H3 | 0.8400 | N41—C46 | 1.428 (4) |
O4—C14 | 1.295 (4) | N42—C48 | 1.429 (4) |
O5—C14 | 1.255 (4) | N43—N44 | 1.246 (4) |
O6—C16 | 1.354 (4) | N43—C59 | 1.436 (4) |
O6—H6 | 0.8400 | N44—C61 | 1.443 (4) |
N1—N2 | 1.252 (4) | C41—C42 | 1.467 (4) |
N1—C6 | 1.423 (4) | C42—C47 | 1.398 (4) |
N2—C8 | 1.424 (4) | C42—C43 | 1.401 (5) |
N3—N4 | 1.247 (4) | C43—C44 | 1.411 (5) |
N3—C19 | 1.438 (4) | C44—C45 | 1.369 (5) |
N4—C21 | 1.441 (4) | C44—H44 | 0.9500 |
C1—C2 | 1.465 (5) | C45—C46 | 1.385 (5) |
C2—C7 | 1.402 (4) | C45—H45 | 0.9500 |
C2—C3 | 1.406 (5) | C46—C47 | 1.385 (4) |
C3—C4 | 1.397 (5) | C47—H47 | 0.9500 |
C4—C5 | 1.375 (5) | C48—C49 | 1.390 (5) |
C4—H4 | 0.9500 | C48—C53 | 1.391 (4) |
C5—C6 | 1.401 (5) | C49—C50 | 1.371 (5) |
C5—H5 | 0.9500 | C49—H49 | 0.9500 |
C6—C7 | 1.374 (5) | C50—C51 | 1.399 (5) |
C7—H7 | 0.9500 | C50—H50 | 0.9500 |
C8—C13 | 1.377 (5) | C51—C52 | 1.372 (5) |
C8—C9 | 1.389 (5) | C51—C67 | 1.515 (5) |
C9—C10 | 1.379 (5) | C52—C53 | 1.390 (5) |
C9—H9 | 0.9500 | C52—H52 | 0.9500 |
C10—C11 | 1.383 (5) | C53—H53 | 0.9500 |
C10—H10 | 0.9500 | C54—C55 | 1.460 (5) |
C11—C12 | 1.386 (5) | C55—C60 | 1.400 (4) |
C11—C27 | 1.528 (5) | C55—C56 | 1.410 (5) |
C12—C13 | 1.394 (5) | C56—C57 | 1.396 (5) |
C12—H12 | 0.9500 | C57—C58 | 1.374 (4) |
C13—H13 | 0.9500 | C57—H57 | 0.9500 |
C14—C15 | 1.466 (5) | C58—C59 | 1.400 (5) |
C15—C20 | 1.393 (4) | C58—H58 | 0.9500 |
C15—C16 | 1.400 (5) | C59—C60 | 1.376 (5) |
C16—C17 | 1.390 (5) | C60—H60 | 0.9500 |
C17—C18 | 1.382 (5) | C61—C66 | 1.376 (5) |
C17—H17 | 0.9500 | C61—C62 | 1.390 (5) |
C18—C19 | 1.397 (5) | C62—C63 | 1.383 (5) |
C18—H18 | 0.9500 | C62—H62 | 0.9500 |
C19—C20 | 1.377 (5) | C63—C64 | 1.376 (5) |
C20—H20 | 0.9500 | C63—H63 | 0.9500 |
C21—C26 | 1.380 (5) | C64—C65 | 1.391 (5) |
C21—C22 | 1.385 (5) | C64—C68 | 1.511 (5) |
C22—C23 | 1.393 (5) | C65—C66 | 1.379 (5) |
C22—H22 | 0.9500 | C65—H65 | 0.9500 |
C23—C24 | 1.388 (5) | C66—H66 | 0.9500 |
C23—H23 | 0.9500 | C67—H671 | 0.9800 |
C24—C25 | 1.386 (5) | C67—H672 | 0.9800 |
C24—C28 | 1.512 (5) | C67—H673 | 0.9800 |
C25—C26 | 1.373 (5) | C68—H681 | 0.9800 |
C25—H25 | 0.9500 | C68—H682 | 0.9800 |
C26—H26 | 0.9500 | C68—H683 | 0.9800 |
C27—H271 | 0.9800 | C69—C70 | 1.525 (5) |
C27—H272 | 0.9800 | C69—H691 | 0.9900 |
C27—H273 | 0.9800 | C69—H692 | 0.9900 |
C28—H281 | 0.9800 | C70—C71 | 1.520 (5) |
C28—H282 | 0.9800 | C70—H701 | 0.9900 |
C28—H283 | 0.9800 | C70—H702 | 0.9900 |
C29—C30 | 1.506 (5) | C71—C72 | 1.517 (5) |
C29—H291 | 0.9900 | C71—H711 | 0.9900 |
C29—H292 | 0.9900 | C71—H712 | 0.9900 |
C30—C31 | 1.540 (5) | C72—H721 | 0.9800 |
C30—H301 | 0.9900 | C72—H722 | 0.9800 |
C30—H302 | 0.9900 | C72—H723 | 0.9800 |
C31—C32 | 1.473 (5) | C73—C74B | 1.499 (5) |
C31—H311 | 0.9900 | C73—C74A | 1.529 (5) |
C31—H312 | 0.9900 | C73—H731 | 0.9900 |
C32—H321 | 0.9800 | C73—H732 | 0.9900 |
C32—H322 | 0.9800 | C73—H733 | 0.9900 |
C32—H323 | 0.9800 | C73—H734 | 0.9900 |
C33—C34A | 1.503 (4) | C74A—C75A | 1.525 (8) |
C33—C34B | 1.506 (5) | C74A—H741 | 0.9900 |
C33—H331 | 0.9900 | C74A—H742 | 0.9900 |
C33—H332 | 0.9900 | C75A—C76A | 1.503 (8) |
C33—H333 | 0.9900 | C75A—H751 | 0.9900 |
C33—H334 | 0.9900 | C75A—H752 | 0.9900 |
C34A—C35A | 1.512 (7) | C76A—H761 | 0.9800 |
C34A—H341 | 0.9900 | C76A—H762 | 0.9800 |
C34A—H342 | 0.9900 | C76A—H763 | 0.9800 |
C35A—C36A | 1.504 (7) | C74B—C75B | 1.524 (8) |
C35A—H351 | 0.9900 | C74B—H743 | 0.9900 |
C35A—H352 | 0.9900 | C74B—H744 | 0.9900 |
C36A—H361 | 0.9800 | C75B—C76B | 1.512 (8) |
C36A—H362 | 0.9800 | C75B—H753 | 0.9900 |
C36A—H363 | 0.9800 | C75B—H754 | 0.9900 |
C34B—C35B | 1.524 (9) | C76B—H764 | 0.9800 |
C34B—H343 | 0.9900 | C76B—H765 | 0.9800 |
C34B—H344 | 0.9900 | C76B—H766 | 0.9800 |
C35B—C36B | 1.500 (9) | C80—C85 | 1.361 (6) |
C35B—H353 | 0.9900 | C80—C81 | 1.376 (6) |
C35B—H354 | 0.9900 | C80—H80 | 0.9500 |
C36B—H364 | 0.9800 | C81—C82 | 1.358 (7) |
C36B—H365 | 0.9800 | C81—H81 | 0.9500 |
C36B—H366 | 0.9800 | C82—C83 | 1.385 (6) |
Sn2—O41 | 2.090 (2) | C82—H82 | 0.9500 |
Sn2—O42 | 2.628 (2) | C83—C84 | 1.359 (6) |
Sn2—O44 | 2.093 (2) | C83—H83 | 0.9500 |
Sn2—O45 | 2.628 (2) | C84—C85 | 1.357 (6) |
Sn2—C69 | 2.121 (3) | C84—H84 | 0.9500 |
Sn2—C73 | 2.117 (3) | C85—H85 | 0.9500 |
| | | |
O1—Sn1—O4 | 83.18 (9) | O44—Sn2—C73 | 103.87 (12) |
O1—Sn1—O5 | 137.43 (8) | O45—Sn2—C69 | 91.09 (11) |
O1—Sn1—C29 | 100.36 (12) | O45—Sn2—C73 | 85.69 (11) |
O1—Sn1—C33 | 106.03 (12) | C69—Sn2—C73 | 144.09 (13) |
O2—Sn1—O4 | 138.10 (8) | O44—Sn2—O45 | 54.15 (7) |
O2—Sn1—O5 | 167.32 (7) | O41—Sn2—O42 | 54.24 (8) |
O2—Sn1—C29 | 86.01 (12) | C41—O41—Sn2 | 105.14 (19) |
O2—Sn1—C33 | 89.64 (12) | C41—O42—Sn2 | 81.07 (19) |
O4—Sn1—C29 | 101.81 (12) | C43—O43—H43 | 109.5 |
O4—Sn1—C33 | 104.98 (11) | C54—O44—Sn2 | 105.22 (19) |
O5—Sn1—C29 | 88.16 (12) | C54—O45—Sn2 | 81.09 (19) |
O5—Sn1—C33 | 88.50 (12) | C56—O46—H46 | 109.5 |
C29—Sn1—C33 | 144.16 (14) | N42—N41—C46 | 115.0 (3) |
O1—Sn1—O2 | 54.94 (8) | N41—N42—C48 | 113.5 (3) |
O4—Sn1—O5 | 54.28 (8) | N44—N43—C59 | 114.6 (3) |
C1—O1—Sn1 | 103.6 (2) | N43—N44—C61 | 114.3 (3) |
C1—O2—Sn1 | 82.0 (2) | O42—C41—O41 | 119.5 (3) |
C3—O3—H3 | 109.5 | O42—C41—C42 | 122.6 (3) |
C14—O4—Sn1 | 105.0 (2) | O41—C41—C42 | 117.9 (3) |
C14—O5—Sn1 | 81.0 (2) | C47—C42—C43 | 119.4 (3) |
C16—O6—H6 | 109.5 | C47—C42—C41 | 119.9 (3) |
N2—N1—C6 | 114.5 (3) | C43—C42—C41 | 120.8 (3) |
N1—N2—C8 | 114.8 (3) | O43—C43—C42 | 122.9 (3) |
N4—N3—C19 | 113.7 (3) | O43—C43—C44 | 118.1 (3) |
N3—N4—C21 | 112.9 (3) | C42—C43—C44 | 119.0 (3) |
O2—C1—O1 | 119.4 (3) | C45—C44—C43 | 120.3 (3) |
O2—C1—C2 | 121.7 (3) | C45—C44—H44 | 119.9 |
O1—C1—C2 | 118.8 (3) | C43—C44—H44 | 119.9 |
C7—C2—C3 | 119.0 (3) | C44—C45—C46 | 121.1 (3) |
C7—C2—C1 | 120.4 (3) | C44—C45—H45 | 119.5 |
C3—C2—C1 | 120.6 (3) | C46—C45—H45 | 119.5 |
O3—C3—C4 | 117.8 (3) | C47—C46—C45 | 119.4 (3) |
O3—C3—C2 | 123.1 (3) | C47—C46—N41 | 114.4 (3) |
C4—C3—C2 | 119.1 (3) | C45—C46—N41 | 126.2 (3) |
C5—C4—C3 | 121.0 (3) | C46—C47—C42 | 120.8 (3) |
C5—C4—H4 | 119.5 | C46—C47—H47 | 119.6 |
C3—C4—H4 | 119.5 | C42—C47—H47 | 119.6 |
C4—C5—C6 | 120.1 (3) | C49—C48—C53 | 119.6 (3) |
C4—C5—H5 | 119.9 | C49—C48—N42 | 124.9 (3) |
C6—C5—H5 | 119.9 | C53—C48—N42 | 115.5 (3) |
C7—C6—C5 | 119.5 (3) | C50—C49—C48 | 119.6 (3) |
C7—C6—N1 | 116.5 (3) | C50—C49—H49 | 120.2 |
C5—C6—N1 | 124.0 (3) | C48—C49—H49 | 120.2 |
C6—C7—C2 | 121.2 (3) | C49—C50—C51 | 121.8 (4) |
C6—C7—H7 | 119.4 | C49—C50—H50 | 119.1 |
C2—C7—H7 | 119.4 | C51—C50—H50 | 119.1 |
C13—C8—C9 | 119.6 (3) | C52—C51—C50 | 117.9 (3) |
C13—C8—N2 | 115.5 (3) | C52—C51—C67 | 121.4 (3) |
C9—C8—N2 | 124.9 (3) | C50—C51—C67 | 120.7 (4) |
C10—C9—C8 | 119.7 (4) | C51—C52—C53 | 121.6 (3) |
C10—C9—H9 | 120.1 | C51—C52—H52 | 119.2 |
C8—C9—H9 | 120.1 | C53—C52—H52 | 119.2 |
C9—C10—C11 | 121.3 (4) | C52—C53—C48 | 119.5 (4) |
C9—C10—H10 | 119.3 | C52—C53—H53 | 120.2 |
C11—C10—H10 | 119.3 | C48—C53—H53 | 120.2 |
C10—C11—C12 | 118.8 (3) | O45—C54—O44 | 119.5 (3) |
C10—C11—C27 | 121.3 (4) | O45—C54—C55 | 122.2 (3) |
C12—C11—C27 | 120.0 (4) | O44—C54—C55 | 118.3 (3) |
C11—C12—C13 | 120.2 (4) | C60—C55—C56 | 118.6 (3) |
C11—C12—H12 | 119.9 | C60—C55—C54 | 120.5 (3) |
C13—C12—H12 | 119.9 | C56—C55—C54 | 121.0 (3) |
C8—C13—C12 | 120.3 (4) | O46—C56—C57 | 118.1 (3) |
C8—C13—H13 | 119.8 | O46—C56—C55 | 122.5 (3) |
C12—C13—H13 | 119.8 | C57—C56—C55 | 119.5 (3) |
O5—C14—O4 | 119.4 (3) | C58—C57—C56 | 121.3 (3) |
O5—C14—C15 | 122.7 (3) | C58—C57—H57 | 119.3 |
O4—C14—C15 | 117.9 (3) | C56—C57—H57 | 119.3 |
C20—C15—C16 | 118.9 (3) | C57—C58—C59 | 119.3 (3) |
C20—C15—C14 | 120.0 (3) | C57—C58—H58 | 120.3 |
C16—C15—C14 | 121.0 (3) | C59—C58—H58 | 120.3 |
O6—C16—C17 | 118.0 (3) | C60—C59—C58 | 120.2 (3) |
O6—C16—C15 | 122.3 (3) | C60—C59—N43 | 115.0 (3) |
C17—C16—C15 | 119.8 (3) | C58—C59—N43 | 124.8 (3) |
C18—C17—C16 | 120.5 (4) | C59—C60—C55 | 121.1 (3) |
C18—C17—H17 | 119.7 | C59—C60—H60 | 119.5 |
C16—C17—H17 | 119.7 | C55—C60—H60 | 119.5 |
C17—C18—C19 | 120.0 (3) | C66—C61—C62 | 120.1 (3) |
C17—C18—H18 | 120.0 | C66—C61—N44 | 116.2 (3) |
C19—C18—H18 | 120.0 | C62—C61—N44 | 123.8 (3) |
C20—C19—C18 | 119.4 (3) | C63—C62—C61 | 118.7 (4) |
C20—C19—N3 | 114.6 (3) | C63—C62—H62 | 120.6 |
C18—C19—N3 | 126.0 (3) | C61—C62—H62 | 120.6 |
C19—C20—C15 | 121.3 (3) | C64—C63—C62 | 122.4 (4) |
C19—C20—H20 | 119.4 | C64—C63—H63 | 118.8 |
C15—C20—H20 | 119.4 | C62—C63—H63 | 118.8 |
C26—C21—C22 | 119.8 (3) | C63—C64—C65 | 117.6 (3) |
C26—C21—N4 | 116.1 (3) | C63—C64—C68 | 121.0 (4) |
C22—C21—N4 | 124.1 (3) | C65—C64—C68 | 121.4 (4) |
C21—C22—C23 | 119.5 (4) | C66—C65—C64 | 121.3 (4) |
C21—C22—H22 | 120.3 | C66—C65—H65 | 119.4 |
C23—C22—H22 | 120.3 | C64—C65—H65 | 119.4 |
C24—C23—C22 | 120.7 (4) | C61—C66—C65 | 119.9 (4) |
C24—C23—H23 | 119.7 | C61—C66—H66 | 120.0 |
C22—C23—H23 | 119.7 | C65—C66—H66 | 120.0 |
C25—C24—C23 | 118.7 (3) | C51—C67—H671 | 109.5 |
C25—C24—C28 | 120.7 (3) | C51—C67—H672 | 109.5 |
C23—C24—C28 | 120.6 (4) | H671—C67—H672 | 109.5 |
C26—C25—C24 | 120.9 (4) | C51—C67—H673 | 109.5 |
C26—C25—H25 | 119.5 | H671—C67—H673 | 109.5 |
C24—C25—H25 | 119.5 | H672—C67—H673 | 109.5 |
C25—C26—C21 | 120.4 (4) | C64—C68—H681 | 109.5 |
C25—C26—H26 | 119.8 | C64—C68—H682 | 109.5 |
C21—C26—H26 | 119.8 | H681—C68—H682 | 109.5 |
C11—C27—H271 | 109.5 | C64—C68—H683 | 109.5 |
C11—C27—H272 | 109.5 | H681—C68—H683 | 109.5 |
H271—C27—H272 | 109.5 | H682—C68—H683 | 109.5 |
C11—C27—H273 | 109.5 | C70—C69—Sn2 | 115.6 (2) |
H271—C27—H273 | 109.5 | C70—C69—H691 | 108.4 |
H272—C27—H273 | 109.5 | Sn2—C69—H691 | 108.4 |
C24—C28—H281 | 109.5 | C70—C69—H692 | 108.4 |
C24—C28—H282 | 109.5 | Sn2—C69—H692 | 108.4 |
H281—C28—H282 | 109.5 | H691—C69—H692 | 107.4 |
C24—C28—H283 | 109.5 | C71—C70—C69 | 112.5 (3) |
H281—C28—H283 | 109.5 | C71—C70—H701 | 109.1 |
H282—C28—H283 | 109.5 | C69—C70—H701 | 109.1 |
C30—C29—Sn1 | 117.0 (3) | C71—C70—H702 | 109.1 |
C30—C29—H291 | 108.1 | C69—C70—H702 | 109.1 |
Sn1—C29—H291 | 108.1 | H701—C70—H702 | 107.8 |
C30—C29—H292 | 108.1 | C72—C71—C70 | 112.6 (3) |
Sn1—C29—H292 | 108.1 | C72—C71—H711 | 109.1 |
H291—C29—H292 | 107.3 | C70—C71—H711 | 109.1 |
C29—C30—C31 | 110.6 (4) | C72—C71—H712 | 109.1 |
C29—C30—H301 | 109.5 | C70—C71—H712 | 109.1 |
C31—C30—H301 | 109.5 | H711—C71—H712 | 107.8 |
C29—C30—H302 | 109.5 | C71—C72—H721 | 109.5 |
C31—C30—H302 | 109.5 | C71—C72—H722 | 109.5 |
H301—C30—H302 | 108.1 | H721—C72—H722 | 109.5 |
C32—C31—C30 | 112.2 (4) | C71—C72—H723 | 109.5 |
C32—C31—H311 | 109.2 | H721—C72—H723 | 109.5 |
C30—C31—H311 | 109.2 | H722—C72—H723 | 109.5 |
C32—C31—H312 | 109.2 | C74B—C73—Sn2 | 114.5 (3) |
C30—C31—H312 | 109.2 | C74A—C73—Sn2 | 115.6 (4) |
H311—C31—H312 | 107.9 | C74A—C73—H731 | 108.4 |
C31—C32—H321 | 109.5 | Sn2—C73—H731 | 108.4 |
C31—C32—H322 | 109.5 | C74A—C73—H732 | 108.4 |
H321—C32—H322 | 109.5 | Sn2—C73—H732 | 108.4 |
C31—C32—H323 | 109.5 | H731—C73—H732 | 107.4 |
H321—C32—H323 | 109.5 | C74B—C73—H733 | 108.6 |
H322—C32—H323 | 109.5 | Sn2—C73—H733 | 108.6 |
C34A—C33—Sn1 | 117.5 (3) | C74B—C73—H734 | 108.6 |
C34B—C33—Sn1 | 117.8 (5) | Sn2—C73—H734 | 108.6 |
C34A—C33—H331 | 107.9 | H733—C73—H734 | 107.6 |
Sn1—C33—H331 | 107.9 | C75A—C74A—C73 | 118.4 (9) |
C34A—C33—H332 | 107.9 | C75A—C74A—H741 | 107.7 |
Sn1—C33—H332 | 107.9 | C73—C74A—H741 | 107.7 |
H331—C33—H332 | 107.2 | C75A—C74A—H742 | 107.7 |
C34B—C33—H333 | 107.9 | C73—C74A—H742 | 107.7 |
Sn1—C33—H333 | 107.9 | H741—C74A—H742 | 107.1 |
C34B—C33—H334 | 107.9 | C76A—C75A—C74A | 111.8 (7) |
Sn1—C33—H334 | 107.9 | C76A—C75A—H751 | 109.3 |
H333—C33—H334 | 107.2 | C74A—C75A—H751 | 109.3 |
C33—C34A—C35A | 114.9 (4) | C76A—C75A—H752 | 109.3 |
C33—C34A—H341 | 108.5 | C74A—C75A—H752 | 109.3 |
C35A—C34A—H341 | 108.5 | H751—C75A—H752 | 107.9 |
C33—C34A—H342 | 108.5 | C75A—C76A—H761 | 109.5 |
C35A—C34A—H342 | 108.5 | C75A—C76A—H762 | 109.5 |
H341—C34A—H342 | 107.5 | H761—C76A—H762 | 109.5 |
C36A—C35A—C34A | 112.4 (5) | C75A—C76A—H763 | 109.5 |
C36A—C35A—H351 | 109.1 | H761—C76A—H763 | 109.5 |
C34A—C35A—H351 | 109.1 | H762—C76A—H763 | 109.5 |
C36A—C35A—H352 | 109.1 | C73—C74B—C75B | 108.2 (5) |
C34A—C35A—H352 | 109.1 | C73—C74B—H743 | 110.1 |
H351—C35A—H352 | 107.8 | C75B—C74B—H743 | 110.1 |
C35A—C36A—H361 | 109.5 | C73—C74B—H744 | 110.1 |
C35A—C36A—H362 | 109.5 | C75B—C74B—H744 | 110.1 |
H361—C36A—H362 | 109.5 | H743—C74B—H744 | 108.4 |
C35A—C36A—H363 | 109.5 | C76B—C75B—C74B | 110.5 (6) |
H361—C36A—H363 | 109.5 | C76B—C75B—H753 | 109.5 |
H362—C36A—H363 | 109.5 | C74B—C75B—H753 | 109.5 |
C33—C34B—C35B | 116.3 (14) | C76B—C75B—H754 | 109.5 |
C33—C34B—H343 | 108.2 | C74B—C75B—H754 | 109.5 |
C35B—C34B—H343 | 108.2 | H753—C75B—H754 | 108.1 |
C33—C34B—H344 | 108.2 | C75B—C76B—H764 | 109.5 |
C35B—C34B—H344 | 108.2 | C75B—C76B—H765 | 109.5 |
H343—C34B—H344 | 107.4 | H764—C76B—H765 | 109.5 |
C36B—C35B—C34B | 111.0 (8) | C75B—C76B—H766 | 109.5 |
C36B—C35B—H353 | 109.4 | H764—C76B—H766 | 109.5 |
C34B—C35B—H353 | 109.4 | H765—C76B—H766 | 109.5 |
C36B—C35B—H354 | 109.4 | C85—C80—C81 | 120.0 (5) |
C34B—C35B—H354 | 109.4 | C85—C80—H80 | 120.0 |
H353—C35B—H354 | 108.0 | C81—C80—H80 | 120.0 |
C35B—C36B—H364 | 109.5 | C82—C81—C80 | 120.9 (5) |
C35B—C36B—H365 | 109.5 | C82—C81—H81 | 119.5 |
H364—C36B—H365 | 109.5 | C80—C81—H81 | 119.5 |
C35B—C36B—H366 | 109.5 | C81—C82—C83 | 118.4 (5) |
H364—C36B—H366 | 109.5 | C81—C82—H82 | 120.8 |
H365—C36B—H366 | 109.5 | C83—C82—H82 | 120.8 |
O41—Sn2—O44 | 82.81 (9) | C84—C83—C82 | 120.4 (5) |
O41—Sn2—O45 | 136.85 (8) | C84—C83—H83 | 119.8 |
O41—Sn2—C69 | 102.61 (11) | C82—C83—H83 | 119.8 |
O41—Sn2—C73 | 104.03 (11) | C85—C84—C83 | 120.7 (5) |
O42—Sn2—O44 | 137.00 (8) | C85—C84—H84 | 119.6 |
O42—Sn2—O45 | 168.83 (7) | C83—C84—H84 | 119.6 |
O42—Sn2—C69 | 86.48 (11) | C84—C85—C80 | 119.6 (5) |
O42—Sn2—C73 | 89.90 (11) | C84—C85—H85 | 120.2 |
O44—Sn2—C69 | 102.97 (12) | C80—C85—H85 | 120.2 |
| | | |
C6—N1—N2—C8 | −178.5 (3) | Sn2—O42—C41—C42 | −179.5 (3) |
C19—N3—N4—C21 | 179.4 (3) | Sn2—O41—C41—O42 | 0.1 (3) |
Sn1—O2—C1—O1 | −2.7 (3) | Sn2—O41—C41—C42 | 179.5 (2) |
Sn1—O2—C1—C2 | 176.7 (3) | O42—C41—C42—C47 | −179.0 (3) |
Sn1—O1—C1—O2 | 3.4 (3) | O41—C41—C42—C47 | 1.6 (4) |
Sn1—O1—C1—C2 | −176.0 (2) | O42—C41—C42—C43 | 1.2 (5) |
O2—C1—C2—C7 | −177.5 (3) | O41—C41—C42—C43 | −178.2 (3) |
O1—C1—C2—C7 | 1.8 (4) | C47—C42—C43—O43 | −179.8 (3) |
O2—C1—C2—C3 | 2.1 (5) | C41—C42—C43—O43 | 0.1 (5) |
O1—C1—C2—C3 | −178.5 (3) | C47—C42—C43—C44 | −0.5 (5) |
C7—C2—C3—O3 | 179.8 (3) | C41—C42—C43—C44 | 179.4 (3) |
C1—C2—C3—O3 | 0.2 (5) | O43—C43—C44—C45 | −179.6 (3) |
C7—C2—C3—C4 | −0.2 (5) | C42—C43—C44—C45 | 1.0 (5) |
C1—C2—C3—C4 | −179.8 (3) | C43—C44—C45—C46 | −0.6 (5) |
O3—C3—C4—C5 | −179.3 (3) | C44—C45—C46—C47 | −0.4 (5) |
C2—C3—C4—C5 | 0.6 (5) | C44—C45—C46—N41 | −179.4 (3) |
C3—C4—C5—C6 | −0.9 (5) | N42—N41—C46—C47 | 174.7 (3) |
C4—C5—C6—C7 | 0.7 (5) | N42—N41—C46—C45 | −6.3 (4) |
C4—C5—C6—N1 | −179.3 (3) | C45—C46—C47—C42 | 1.0 (5) |
N2—N1—C6—C7 | −177.7 (3) | N41—C46—C47—C42 | −179.9 (3) |
N2—N1—C6—C5 | 2.3 (5) | C43—C42—C47—C46 | −0.6 (5) |
C5—C6—C7—C2 | −0.3 (5) | C41—C42—C47—C46 | 179.6 (3) |
N1—C6—C7—C2 | 179.7 (3) | N41—N42—C48—C49 | −2.2 (5) |
C3—C2—C7—C6 | 0.0 (5) | N41—N42—C48—C53 | 177.9 (3) |
C1—C2—C7—C6 | 179.6 (3) | C53—C48—C49—C50 | 0.3 (5) |
N1—N2—C8—C13 | 179.6 (3) | N42—C48—C49—C50 | −179.5 (3) |
N1—N2—C8—C9 | −0.6 (5) | C48—C49—C50—C51 | −0.1 (5) |
C13—C8—C9—C10 | −1.3 (5) | C49—C50—C51—C52 | −0.6 (5) |
N2—C8—C9—C10 | 179.0 (3) | C49—C50—C51—C67 | 179.6 (3) |
C8—C9—C10—C11 | −0.2 (5) | C50—C51—C52—C53 | 1.0 (5) |
C9—C10—C11—C12 | 1.4 (5) | C67—C51—C52—C53 | −179.2 (3) |
C9—C10—C11—C27 | −178.8 (3) | C51—C52—C53—C48 | −0.8 (5) |
C10—C11—C12—C13 | −1.2 (5) | C49—C48—C53—C52 | 0.1 (5) |
C27—C11—C12—C13 | 179.0 (3) | N42—C48—C53—C52 | 179.9 (3) |
C9—C8—C13—C12 | 1.5 (5) | Sn2—O45—C54—O44 | −1.3 (3) |
N2—C8—C13—C12 | −178.8 (3) | Sn2—O45—C54—C55 | 179.2 (3) |
C11—C12—C13—C8 | −0.2 (5) | Sn2—O44—C54—O45 | 1.6 (3) |
Sn1—O5—C14—O4 | 4.2 (3) | Sn2—O44—C54—C55 | −178.8 (2) |
Sn1—O5—C14—C15 | −174.9 (3) | O45—C54—C55—C60 | 178.9 (3) |
Sn1—O4—C14—O5 | −5.4 (3) | O44—C54—C55—C60 | −0.6 (4) |
Sn1—O4—C14—C15 | 173.7 (2) | O45—C54—C55—C56 | −0.7 (5) |
O5—C14—C15—C20 | 178.7 (3) | O44—C54—C55—C56 | 179.8 (3) |
O4—C14—C15—C20 | −0.3 (4) | C60—C55—C56—O46 | −179.9 (3) |
O5—C14—C15—C16 | 2.9 (5) | C54—C55—C56—O46 | −0.3 (5) |
O4—C14—C15—C16 | −176.1 (3) | C60—C55—C56—C57 | −0.4 (4) |
C20—C15—C16—O6 | 179.8 (3) | C54—C55—C56—C57 | 179.2 (3) |
C14—C15—C16—O6 | −4.3 (5) | O46—C56—C57—C58 | 179.1 (3) |
C20—C15—C16—C17 | −0.8 (5) | C55—C56—C57—C58 | −0.4 (5) |
C14—C15—C16—C17 | 175.1 (3) | C56—C57—C58—C59 | 0.9 (5) |
O6—C16—C17—C18 | −178.7 (3) | C57—C58—C59—C60 | −0.5 (5) |
C15—C16—C17—C18 | 1.9 (5) | C57—C58—C59—N43 | 178.4 (3) |
C16—C17—C18—C19 | −1.2 (5) | N44—N43—C59—C60 | −173.1 (3) |
C17—C18—C19—C20 | −0.6 (5) | N44—N43—C59—C58 | 8.0 (5) |
C17—C18—C19—N3 | −179.1 (3) | C58—C59—C60—C55 | −0.2 (5) |
N4—N3—C19—C20 | −179.5 (3) | N43—C59—C60—C55 | −179.3 (3) |
N4—N3—C19—C18 | −0.9 (5) | C56—C55—C60—C59 | 0.7 (5) |
C18—C19—C20—C15 | 1.7 (5) | C54—C55—C60—C59 | −178.9 (3) |
N3—C19—C20—C15 | −179.6 (3) | N43—N44—C61—C66 | −175.9 (3) |
C16—C15—C20—C19 | −1.0 (5) | N43—N44—C61—C62 | 4.4 (5) |
C14—C15—C20—C19 | −176.9 (3) | C66—C61—C62—C63 | −1.5 (5) |
N3—N4—C21—C26 | 173.7 (3) | N44—C61—C62—C63 | 178.2 (3) |
N3—N4—C21—C22 | −8.1 (5) | C61—C62—C63—C64 | 1.2 (5) |
C26—C21—C22—C23 | −0.5 (5) | C62—C63—C64—C65 | −0.5 (5) |
N4—C21—C22—C23 | −178.7 (3) | C62—C63—C64—C68 | −179.6 (3) |
C21—C22—C23—C24 | −0.5 (5) | C63—C64—C65—C66 | 0.2 (5) |
C22—C23—C24—C25 | 0.7 (5) | C68—C64—C65—C66 | 179.3 (3) |
C22—C23—C24—C28 | −179.3 (3) | C62—C61—C66—C65 | 1.2 (5) |
C23—C24—C25—C26 | 0.1 (5) | N44—C61—C66—C65 | −178.5 (3) |
C28—C24—C25—C26 | −179.9 (3) | C64—C65—C66—C61 | −0.5 (5) |
C24—C25—C26—C21 | −1.1 (5) | Sn2—C69—C70—C71 | −72.9 (4) |
C22—C21—C26—C25 | 1.3 (5) | C69—C70—C71—C72 | 178.3 (3) |
N4—C21—C26—C25 | 179.6 (3) | Sn2—C73—C74A—C75A | 55.7 (8) |
Sn1—C29—C30—C31 | −75.0 (4) | C73—C74A—C75A—C76A | 65.6 (16) |
C29—C30—C31—C32 | 177.9 (4) | Sn2—C73—C74B—C75B | −77.7 (9) |
Sn1—C33—C34A—C35A | −69.3 (7) | C73—C74B—C75B—C76B | −176.5 (9) |
C33—C34A—C35A—C36A | −178.3 (7) | C85—C80—C81—C82 | −0.3 (7) |
Sn1—C33—C34B—C35B | 49.1 (11) | C80—C81—C82—C83 | −0.2 (7) |
C33—C34B—C35B—C36B | 80 (2) | C81—C82—C83—C84 | 1.3 (7) |
C46—N41—N42—C48 | 179.5 (3) | C82—C83—C84—C85 | −2.0 (7) |
C59—N43—N44—C61 | −177.5 (3) | C83—C84—C85—C80 | 1.5 (7) |
Sn2—O42—C41—O41 | −0.1 (3) | C81—C80—C85—C84 | −0.4 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.84 | 1.88 | 2.618 (3) | 145 |
O6—H6···O5 | 0.84 | 1.89 | 2.631 (3) | 146 |
O43—H43···O42 | 0.84 | 1.90 | 2.635 (3) | 146 |
O46—H46···O45 | 0.84 | 1.91 | 2.627 (3) | 142 |
C28—H281···O4i | 0.98 | 2.56 | 3.385 (5) | 142 |
C73—H733···O41ii | 0.99 | 2.58 | 3.540 (5) | 162 |
C30—H301···Cg7 | 0.99 | 2.83 | 3.717 (5) | 149 |
C34A—H341···Cg4iii | 0.99 | 2.64 | 3.586 (5) | 160 |
C34B—H344···Cg4iii | 0.99 | 2.73 | 3.662 (13) | 157 |
C70—H702···Cg6iii | 0.99 | 2.71 | 3.654 (4) | 159 |
C74A—H741···Cg9ii | 0.99 | 2.69 | 3.643 (7) | 161 |
C74B—H743···Cg9ii | 0.99 | 2.83 | 3.692 (7) | 146 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z. |
Table 4. Comparison of the unit-cell parameters of compounds
(I)–(VI)a. top | (I) | (II) | (III) | (IV) | (V) | (VI) |
a (Å) | 10.1883 (1) | 12.0462 (1) | 9.8270 (2) | 11.6044 (1) | 9.3399 (1) | 9.6410 (1) |
b (Å) | 12.9209 (1) | 13.6264 (2) | 12.1642 (3) | 11.5675 (1) | 25.1934 (2) | 12.1897 (2) |
c (Å) | 23.0447 (2) | 22.8143 (3) | 14.9382 (3) | 25.9005 (3) | 15.4687 (2) | 15.1748 (2) |
α (°) | 102.3524 (4) | 102.2665 (6) | 93.357 (1) | 90 | 90 | 94.1325 (7) |
β (°) | 95.2584 (4) | 100.3180 (6) | 100.016 (1) | 97.3428 (4) | 94.1425 (3) | 98.7581 (7) |
γ (°) | 104.1530 (5) | 91.6029 (6) | 103.805 (1) | 90 | 90 | 103.6085 (5) |
V (Å3) | 2840.09 (4) | 3591.71 (8) | 1698.29 (7) | 3448.21 (6) | 3630.34 (7) | 1702.24 (4) |
Space group | P1 | P1 | P1 | P21/c | P21/c | P1 |
Note: (a) details for compounds (III)–(VI) are taken from
Basu Baul et al. (2004). |
Table 7. Geometry of the π–π interactions in compounds (I)–(VI) (Å, °).
Cg are the centroids of the 2-hydroxyphenyl and terminyl aryl rings
defined by the following atoms: Cg1 C2–C7; Cg2 C8–C13;
Cg3 C15–C20; Cg4 C21–C26; Cg5 C42–C47;
Cg6 C48–C53; Cg7 C55–C60; Cg8 C61–C66;
Cg9 C80–C86.
In structures with disordered carboxylate ligands, only the major conformation
is considered.
α is the dihedral angle between planes I and J, β is the angle
between the CgI···CgJ vector and the normal to the plane
I,
γ is the angle between the CgI···CgJ vector and the normal to
plane J, CgI···PlaneJ is the perpendicular distance of
CgI from the plane of ring J, CgJ···PerpI is the
perpendicular distance of CgJ from the plane of ring I, and the
slippage is the distance between CgI and the perpendicular projection
of CgJ on the plane of ring I (calculated with PLATON;
Spek, 2009). topInteraction | CgI···CgJ | CgI···PlaneJ | CgJ···PlaneI | α | β | γ | Slippage |
Compound (I) | | | | | | | |
Cg1···Cg1i | 3.8578 (16) | 3.5175 (11) | 3.5174 (11) | 0 | 24.3 | 24.3 | 1.59 |
Cg1···Cg3ii | 3.6778 (16) | 3.4955 (11) | 3.4628 (11) | 7.28 (13) | 19.7 | 18.1 | 1.24 |
Cg5···Cg7ii | 3.6492 (16) | 3.4107 (11) | 3.4990 (11) | 4.65 (13) | 16.5 | 20.8 | 1.04 |
| | | | | | | |
Compound (II) | | | | | | | |
Cg1···Cg1iii | 4.082 (2) | 3.6860 (14) | 3.6861 (14) | 0 | 25.4 | 25.4 | 1.75 |
Cg1···Cg3iv | 4.028 (2) | 3.7388 (14) | 3.7789 (15) | 13.98 (17) | 20.3 | 21.8 | 1.39 |
Cg2···Cg6v | 3.780 (2) | 3.5022 (15) | 3.5833 (15) | 6.24 (18) | 18.5 | 22.1 | 1.20 |
Cg2···Cg8vi | 3.987 (2) | 3.7113 (15) | 3.8503 (15) | 12.92 (18) | 15.1 | 21.5 | 1.04 |
Cg3···Cg9 | 3.680 (2) | 3.5404 (15) | 3.505 (2) | 4.5 (2) | 17.8 | 15.8 | 1.12 |
Cg4···Cg8v | 3.805 (2) | 3.4786 (15) | 3.5700 (15) | 9.33 (18) | 20.3 | 23.9 | 1.32 |
Cg5···Cg5vii | 3.9809 (19) | 3.6944 (14) | 3.6945 (14) | 0 | 21.9 | 21.9 | 1.48 |
Cg5···Cg7i | 3.955 (2) | 3.4673 (14) | 3.5635 (14) | 4.05 (16) | 25.7 | 28.8 | 1.72 |
| | | | | | | |
Compound (III) | | | | | | | |
Cg1···Cg3viii | 3.6225 (14) | 3.4408 (9) | 3.4347 (10) | 1.86 (11) | 18.5 | 18.2 | 1.15 |
Cg2···Cg4viii | 4.1928 (15) | 3.6557 (11) | 3.4482 (11) | 8.09 (13) | 34.7 | 29.3 | 2.39 |
| | | | | | | |
Compound (IV) | | | | | | | |
Cg1···Cg3ix | 3.803 (9) | 3.4525 (10) | 3.440 (9) | 0.5 (7) | 25.2 | 24.8 | 1.62 |
Cg2···Cg4ix | 3.816 (7) | 3.4796 (12) | 3.488 (7) | 3.6 (6) | 23.9 | 24.2 | 1.55 |
Cg1···Cg2x | 4.1647 (16) | 3.4726 (10) | 3.5033 (12) | 1.95 (13) | 32.7 | 33.5 | 2.25 |
| | | | | | | |
Compound (V) | | | | | | | |
Cg1···Cg4vii | 3.700 (6) | 3.5000 (8) | 3.481 (5) | 4.1 (4) | 19.8 | 19.0 | 1.25 |
Cg2···Cg3vii | 3.799 (4) | 3.5128 (8) | 3.398 (4) | 4.2 (3) | 26.6 | 22.4 | 1.70 |
| | | | | | | |
Compound (VI) | | | | | | | |
Cg1···Cg3viii | 3.6310 (13) | 3.4220 (10) | 3.4344 (9) | 3.21 (11) | 18.9 | 19.5 | 1.18 |
Cg2···Cg4viii | 4.2534 (14) | 3.6431 (11) | 3.3332 (10) | 7.43 (12) | 38.4 | 31.1 | 2.64 |
Symmetry codes: (i) -x+1, -y+1, -z+1;
(ii) x+1, y, z;
(iii) -x, -y+1, -z;
(iv) -x+1, -y+1, -z;
(v) -x+1, -y, -z;
(vi) -x, -y, -z;
(vii) -x+2, -y+1, -z+1;
(viii) x-1, y, z; (ix) x, y+1, z;
(x) -x+1, -y+2, -z+1. |
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