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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(CH3)2(C14H11N2O3)2], and di-n-butyl­bis­{2-hy­droxy-5-[(E)-2-(4-methyl­phen­yl)diazen-1-yl]­ben­zo­ato}tin(IV) benzene hemisolvate, [Sn(C4H9)2(C14H11N2O3)2]·0.5C6H6, exhibit the usual skew-trapezoidal bipyramidal coordination geometry observed for related complexes of this class. Each structure has two independent mol­ecules of the SnIV 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616004435/sk3620sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004435/sk3620Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2053229616004435/sk3620Isup4.cdx
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004435/sk3620IIsup3.hkl
Contains datablock II

cdx

Chemdraw file https://doi.org/10.1107/S2053229616004435/sk3620IIsup5.cdx
Supplementary material

CCDC references: 1468791; 1468790

Computing details top

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 = 659.25Dx = 1.541 Mg m3
Triclinic, P1Melting point: 496 K
a = 10.1883 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.9209 (1) ÅCell parameters from 77568 reflections
c = 23.0447 (2) Åθ = 2.0–30.0°
α = 102.3524 (4)°µ = 0.95 mm1
β = 95.2584 (4)°T = 160 K
γ = 104.1530 (5)°Prism, yellow
V = 2840.09 (4) Å30.30 × 0.20 × 0.11 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
16590 independent reflections
Radiation source: Nonius FR590 sealed tube generator10414 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.070
Detector resolution: 9 pixels mm-1θmax = 30.0°, θmin = 2.1°
φ and ω scans with κ offsetsh = 1414
Absorption correction: multi-scan
(Blessing, 1995)
k = 1818
Tmin = 0.805, Tmax = 0.912l = 3232
69932 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H 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 reflectionsΔρmax = 1.65 e Å3
763 parametersΔρmin = 1.07 e Å3
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
xyzUiso*/Ueq
Sn10.10136 (2)0.38257 (2)0.32223 (2)0.02512 (6)
O10.25573 (18)0.50245 (15)0.38461 (8)0.0285 (4)
O20.34413 (19)0.36401 (16)0.35559 (9)0.0337 (5)
O30.5996 (2)0.38169 (18)0.39426 (10)0.0363 (5)
H30.521 (4)0.353 (4)0.3804 (19)0.094 (17)*
O40.00723 (19)0.50043 (15)0.34064 (8)0.0311 (5)
O50.14973 (19)0.36505 (15)0.27117 (9)0.0314 (5)
O60.3961 (2)0.38172 (17)0.23716 (9)0.0336 (5)
H60.344 (3)0.350 (3)0.2374 (16)0.052 (12)*
N10.6293 (2)0.8055 (2)0.52231 (10)0.0304 (6)
N20.7395 (2)0.85626 (19)0.55732 (10)0.0304 (6)
N30.2189 (2)0.81187 (18)0.37749 (10)0.0266 (5)
N40.2911 (2)0.87516 (19)0.36858 (10)0.0293 (5)
C10.3583 (3)0.4601 (2)0.38642 (12)0.0263 (6)
C20.4893 (3)0.5268 (2)0.42365 (12)0.0239 (6)
C30.6026 (3)0.4841 (2)0.42542 (12)0.0272 (6)
C40.7282 (3)0.5489 (2)0.45927 (13)0.0308 (7)
H40.80560.52020.45990.037*
C50.7396 (3)0.6539 (2)0.49150 (12)0.0292 (7)
H50.82490.69740.51460.035*
C60.6270 (3)0.6975 (2)0.49066 (12)0.0262 (6)
C70.5031 (3)0.6339 (2)0.45627 (12)0.0273 (6)
H70.42680.66380.45500.033*
C80.7434 (3)0.9646 (2)0.58893 (12)0.0281 (6)
C90.6412 (3)1.0163 (3)0.58016 (14)0.0378 (8)
H90.56250.97950.55080.045*
C100.6540 (3)1.1212 (3)0.61410 (14)0.0399 (8)
H100.58311.15560.60820.048*
C110.7696 (3)1.1776 (2)0.65696 (13)0.0344 (7)
C120.8729 (3)1.1262 (2)0.66414 (13)0.0349 (7)
H120.95311.16370.69250.042*
C130.8601 (3)1.0205 (2)0.63025 (13)0.0328 (7)
H130.93160.98640.63540.039*
C140.1235 (3)0.4599 (2)0.30469 (12)0.0272 (6)
C150.2184 (3)0.5285 (2)0.30485 (12)0.0247 (6)
C160.3503 (3)0.4863 (2)0.27060 (12)0.0266 (6)
C170.4382 (3)0.5535 (2)0.27123 (13)0.0296 (7)
H170.52670.52520.24780.035*
C180.3987 (3)0.6600 (2)0.30525 (12)0.0282 (6)
H180.46020.70460.30550.034*
C190.2681 (3)0.7035 (2)0.33971 (12)0.0249 (6)
C200.1805 (3)0.6370 (2)0.33952 (12)0.0252 (6)
H200.09270.66560.36350.030*
C210.2457 (3)0.9831 (2)0.40756 (12)0.0257 (6)
C220.1456 (3)1.0157 (2)0.45712 (13)0.0365 (7)
H220.09900.96510.46700.044*
C230.1129 (3)1.1218 (2)0.49247 (13)0.0379 (8)
H230.04351.14320.52660.045*
C240.1792 (3)1.1978 (2)0.47928 (13)0.0290 (6)
C250.2793 (3)1.1641 (2)0.42959 (15)0.0398 (8)
H250.32641.21460.41980.048*
C260.3126 (3)1.0579 (2)0.39364 (14)0.0373 (8)
H260.38151.03640.35940.045*
C270.7830 (3)1.2919 (3)0.69461 (15)0.0473 (9)
H2710.71471.28840.72190.071*
H2720.76791.33950.66820.071*
H2730.87501.32190.71800.071*
C280.1414 (3)1.3135 (2)0.51864 (14)0.0372 (8)
H2810.20281.35390.50470.056*
H2820.04661.35090.51640.056*
H2830.15051.31080.56030.056*
C290.1619 (3)0.3892 (3)0.23862 (13)0.0387 (8)
H2910.17130.46340.23270.058*
H2920.09270.33580.20680.058*
H2930.24990.37160.23710.058*
C300.0148 (3)0.2604 (2)0.36471 (14)0.0385 (8)
H3010.01380.29420.40200.058*
H3020.08260.22180.37410.058*
H3030.06500.20790.33800.058*
Sn20.60835 (2)0.10939 (2)0.20193 (2)0.02463 (6)
O410.50211 (18)0.00346 (15)0.15816 (8)0.0288 (4)
O420.35771 (19)0.16857 (15)0.18648 (9)0.0315 (5)
O430.1099 (2)0.20069 (18)0.15594 (11)0.0387 (6)
H430.162 (4)0.214 (3)0.1736 (16)0.054 (13)*
O440.77008 (19)0.03372 (15)0.18092 (9)0.0319 (5)
O450.86084 (19)0.09139 (16)0.23033 (8)0.0323 (5)
O461.1085 (2)0.02763 (18)0.25580 (10)0.0376 (5)
H461.038 (3)0.073 (3)0.2515 (15)0.051 (11)*
N410.2835 (2)0.23287 (19)0.02011 (10)0.0292 (5)
N420.2053 (2)0.2628 (2)0.01555 (10)0.0306 (6)
N431.1311 (2)0.3884 (2)0.11860 (11)0.0314 (6)
N441.2365 (2)0.4641 (2)0.11707 (10)0.0313 (6)
C410.3834 (3)0.0701 (2)0.15825 (12)0.0265 (6)
C420.2859 (3)0.0273 (2)0.12326 (12)0.0247 (6)
C430.1556 (3)0.0956 (2)0.12328 (13)0.0287 (6)
C440.0657 (3)0.0551 (2)0.08834 (13)0.0318 (7)
H440.02220.10140.08800.038*
C450.1047 (3)0.0524 (2)0.05437 (13)0.0305 (7)
H450.04280.07980.03100.037*
C460.2346 (3)0.1215 (2)0.05404 (12)0.0269 (6)
C470.3226 (3)0.0808 (2)0.08837 (12)0.0269 (6)
H470.41060.12740.08830.032*
C480.2533 (3)0.3745 (2)0.04892 (12)0.0281 (6)
C490.3806 (3)0.4456 (2)0.04775 (13)0.0353 (7)
H490.44260.41960.02390.042*
C500.4164 (3)0.5536 (3)0.08129 (13)0.0383 (8)
H500.50300.60130.08020.046*
C510.3265 (3)0.5931 (2)0.11675 (13)0.0320 (7)
C520.2020 (3)0.5218 (3)0.11793 (13)0.0352 (7)
H520.13970.54790.14160.042*
C530.1657 (3)0.4131 (3)0.08544 (13)0.0332 (7)
H530.08090.36480.08810.040*
C540.8724 (3)0.0069 (2)0.20316 (12)0.0294 (6)
C551.0001 (3)0.0942 (2)0.19579 (12)0.0260 (6)
C561.1115 (3)0.0731 (2)0.22349 (12)0.0275 (6)
C571.2287 (3)0.1595 (2)0.21874 (12)0.0310 (7)
H571.30260.14600.23880.037*
C581.2383 (3)0.2631 (2)0.18551 (13)0.0306 (7)
H581.31890.32080.18240.037*
C591.1297 (3)0.2847 (2)0.15587 (12)0.0272 (6)
C601.0120 (3)0.2002 (2)0.16222 (12)0.0284 (6)
H600.93730.21490.14320.034*
C611.2412 (3)0.5668 (2)0.07783 (12)0.0281 (6)
C621.1566 (3)0.5803 (3)0.03444 (13)0.0368 (7)
H621.09010.51840.02930.044*
C631.1693 (3)0.6832 (3)0.00090 (13)0.0386 (8)
H631.11110.69160.03050.046*
C641.2655 (3)0.7757 (2)0.00558 (13)0.0328 (7)
C651.3511 (3)0.7603 (3)0.04800 (14)0.0396 (8)
H651.41930.82180.05240.047*
C661.3393 (3)0.6569 (2)0.08424 (14)0.0367 (7)
H661.39840.64800.11340.044*
C670.3666 (3)0.7128 (3)0.15153 (14)0.0426 (8)
H6710.43120.72260.18780.064*
H6720.40990.75930.12630.064*
H6730.28470.73380.16300.064*
C681.2762 (3)0.8892 (3)0.03241 (13)0.0428 (8)
H6811.25500.88380.07250.064*
H6821.36950.93620.03600.064*
H6831.21110.92110.01340.064*
C690.5492 (3)0.1368 (3)0.29454 (12)0.0376 (8)
H6910.60330.18070.31630.056*
H6920.45180.17640.30520.056*
H6930.56470.06600.30550.056*
C700.6591 (3)0.1953 (2)0.13960 (13)0.0330 (7)
H7010.65660.15400.09890.049*
H7020.59310.26800.14820.049*
H7030.75130.20410.14250.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02441 (11)0.02026 (11)0.02735 (11)0.00554 (8)0.00105 (8)0.00053 (8)
O10.0234 (10)0.0262 (11)0.0306 (11)0.0066 (9)0.0030 (8)0.0010 (8)
O20.0301 (11)0.0228 (11)0.0426 (12)0.0067 (9)0.0002 (9)0.0009 (9)
O30.0316 (13)0.0246 (12)0.0501 (14)0.0115 (10)0.0009 (10)0.0016 (10)
O40.0254 (11)0.0260 (11)0.0372 (12)0.0095 (9)0.0035 (9)0.0017 (9)
O50.0296 (11)0.0233 (11)0.0359 (12)0.0083 (9)0.0002 (9)0.0032 (9)
O60.0261 (12)0.0244 (12)0.0407 (13)0.0030 (10)0.0044 (9)0.0039 (9)
N10.0265 (13)0.0288 (14)0.0313 (13)0.0045 (11)0.0021 (10)0.0021 (11)
N20.0287 (13)0.0272 (14)0.0319 (14)0.0046 (11)0.0008 (11)0.0047 (11)
N30.0264 (13)0.0214 (13)0.0307 (13)0.0071 (10)0.0022 (10)0.0039 (10)
N40.0297 (13)0.0247 (13)0.0337 (14)0.0082 (11)0.0055 (10)0.0063 (11)
C10.0254 (15)0.0254 (16)0.0266 (15)0.0051 (12)0.0031 (12)0.0055 (12)
C20.0224 (14)0.0252 (15)0.0246 (14)0.0062 (12)0.0024 (11)0.0079 (12)
C30.0314 (16)0.0259 (16)0.0269 (15)0.0101 (13)0.0060 (12)0.0085 (12)
C40.0239 (15)0.0325 (17)0.0372 (17)0.0102 (13)0.0013 (12)0.0097 (14)
C50.0212 (15)0.0333 (17)0.0312 (16)0.0050 (13)0.0001 (12)0.0079 (13)
C60.0266 (15)0.0264 (16)0.0243 (14)0.0058 (12)0.0039 (11)0.0052 (12)
C70.0276 (15)0.0254 (16)0.0282 (15)0.0087 (13)0.0040 (12)0.0033 (12)
C80.0298 (16)0.0250 (16)0.0273 (15)0.0036 (13)0.0036 (12)0.0062 (12)
C90.0306 (17)0.0355 (19)0.0417 (19)0.0053 (14)0.0001 (14)0.0046 (15)
C100.0354 (18)0.0325 (18)0.051 (2)0.0106 (15)0.0091 (15)0.0071 (15)
C110.0419 (19)0.0252 (17)0.0328 (17)0.0017 (14)0.0129 (14)0.0055 (13)
C120.0378 (18)0.0304 (18)0.0309 (16)0.0007 (14)0.0004 (13)0.0095 (13)
C130.0333 (17)0.0253 (16)0.0360 (17)0.0027 (13)0.0003 (13)0.0077 (13)
C140.0264 (15)0.0240 (16)0.0284 (15)0.0059 (12)0.0027 (12)0.0021 (12)
C150.0261 (15)0.0236 (15)0.0229 (14)0.0053 (12)0.0030 (11)0.0047 (11)
C160.0277 (15)0.0263 (16)0.0224 (14)0.0033 (13)0.0016 (11)0.0038 (12)
C170.0203 (14)0.0301 (17)0.0342 (16)0.0031 (13)0.0005 (12)0.0050 (13)
C180.0244 (15)0.0276 (16)0.0338 (16)0.0091 (13)0.0040 (12)0.0077 (13)
C190.0239 (14)0.0216 (15)0.0273 (15)0.0033 (12)0.0025 (11)0.0060 (12)
C200.0220 (14)0.0266 (16)0.0260 (15)0.0067 (12)0.0005 (11)0.0054 (12)
C210.0257 (15)0.0236 (15)0.0285 (15)0.0083 (12)0.0060 (12)0.0051 (12)
C220.0438 (19)0.0282 (17)0.0385 (18)0.0182 (15)0.0039 (14)0.0045 (14)
C230.046 (2)0.0337 (18)0.0327 (17)0.0169 (16)0.0036 (14)0.0022 (14)
C240.0275 (16)0.0263 (16)0.0350 (16)0.0085 (13)0.0113 (13)0.0073 (13)
C250.0376 (18)0.0252 (17)0.059 (2)0.0165 (15)0.0045 (16)0.0104 (15)
C260.0335 (17)0.0300 (18)0.0449 (19)0.0109 (14)0.0120 (14)0.0065 (14)
C270.056 (2)0.0306 (19)0.050 (2)0.0054 (17)0.0137 (17)0.0038 (16)
C280.0387 (18)0.0283 (17)0.0425 (19)0.0126 (15)0.0060 (14)0.0002 (14)
C290.0324 (17)0.045 (2)0.0311 (17)0.0008 (15)0.0072 (13)0.0050 (15)
C300.0430 (19)0.0277 (17)0.0409 (19)0.0022 (15)0.0030 (15)0.0100 (14)
Sn20.02260 (11)0.02230 (11)0.02507 (11)0.00392 (8)0.00101 (8)0.00108 (8)
O410.0215 (10)0.0234 (11)0.0358 (11)0.0027 (8)0.0050 (8)0.0012 (9)
O420.0274 (11)0.0230 (11)0.0370 (12)0.0042 (9)0.0034 (9)0.0043 (9)
O430.0268 (12)0.0280 (13)0.0500 (15)0.0013 (10)0.0048 (11)0.0035 (10)
O440.0265 (11)0.0259 (11)0.0357 (12)0.0010 (9)0.0071 (9)0.0004 (9)
O450.0304 (11)0.0260 (11)0.0339 (11)0.0018 (9)0.0026 (9)0.0012 (9)
O460.0378 (13)0.0275 (13)0.0409 (13)0.0030 (11)0.0115 (10)0.0010 (10)
N410.0281 (13)0.0256 (14)0.0338 (14)0.0080 (11)0.0049 (11)0.0062 (11)
N420.0330 (14)0.0310 (14)0.0302 (13)0.0128 (12)0.0042 (11)0.0078 (11)
N430.0280 (13)0.0286 (14)0.0340 (14)0.0031 (11)0.0069 (11)0.0045 (11)
N440.0298 (14)0.0272 (14)0.0346 (14)0.0039 (11)0.0069 (11)0.0066 (11)
C410.0236 (15)0.0242 (16)0.0277 (15)0.0045 (12)0.0021 (11)0.0027 (12)
C420.0197 (14)0.0249 (15)0.0267 (15)0.0035 (12)0.0011 (11)0.0046 (12)
C430.0232 (15)0.0257 (16)0.0333 (16)0.0035 (12)0.0026 (12)0.0058 (13)
C440.0202 (15)0.0352 (18)0.0359 (17)0.0013 (13)0.0021 (12)0.0085 (14)
C450.0251 (15)0.0369 (18)0.0333 (16)0.0133 (14)0.0058 (12)0.0102 (14)
C460.0268 (15)0.0265 (16)0.0262 (15)0.0056 (13)0.0028 (12)0.0062 (12)
C470.0229 (14)0.0279 (16)0.0281 (15)0.0040 (12)0.0011 (11)0.0076 (12)
C480.0304 (16)0.0280 (16)0.0268 (15)0.0102 (13)0.0019 (12)0.0070 (12)
C490.0322 (17)0.0362 (19)0.0354 (17)0.0106 (14)0.0098 (13)0.0007 (14)
C500.0310 (17)0.0387 (19)0.0390 (18)0.0050 (15)0.0026 (14)0.0024 (15)
C510.0370 (17)0.0314 (17)0.0280 (16)0.0113 (14)0.0023 (13)0.0066 (13)
C520.0429 (19)0.0358 (19)0.0316 (17)0.0180 (16)0.0131 (14)0.0067 (14)
C530.0311 (16)0.0372 (18)0.0326 (16)0.0095 (14)0.0076 (13)0.0099 (14)
C540.0310 (16)0.0295 (17)0.0237 (15)0.0033 (13)0.0018 (12)0.0050 (12)
C550.0227 (14)0.0275 (16)0.0245 (14)0.0037 (12)0.0025 (11)0.0039 (12)
C560.0299 (16)0.0266 (16)0.0235 (14)0.0065 (13)0.0007 (12)0.0037 (12)
C570.0254 (15)0.0347 (18)0.0307 (16)0.0047 (13)0.0084 (12)0.0057 (13)
C580.0260 (15)0.0291 (17)0.0340 (16)0.0017 (13)0.0071 (12)0.0075 (13)
C590.0255 (15)0.0254 (16)0.0308 (16)0.0059 (12)0.0060 (12)0.0073 (12)
C600.0253 (15)0.0325 (17)0.0262 (15)0.0055 (13)0.0056 (12)0.0065 (12)
C610.0261 (15)0.0258 (16)0.0316 (16)0.0056 (13)0.0046 (12)0.0071 (13)
C620.0297 (17)0.0408 (19)0.0359 (17)0.0024 (14)0.0090 (13)0.0075 (15)
C630.0341 (18)0.046 (2)0.0307 (17)0.0077 (16)0.0085 (13)0.0004 (15)
C640.0344 (17)0.0338 (18)0.0270 (16)0.0109 (14)0.0028 (13)0.0017 (13)
C650.0434 (19)0.0279 (18)0.0436 (19)0.0027 (15)0.0069 (15)0.0085 (15)
C660.0416 (19)0.0303 (18)0.0372 (18)0.0058 (15)0.0159 (14)0.0061 (14)
C670.051 (2)0.037 (2)0.0388 (19)0.0152 (16)0.0123 (15)0.0007 (15)
C680.052 (2)0.040 (2)0.0330 (18)0.0188 (17)0.0033 (15)0.0020 (15)
C690.0452 (19)0.0366 (19)0.0267 (16)0.0110 (15)0.0026 (14)0.0020 (14)
C700.0264 (16)0.0391 (19)0.0338 (17)0.0063 (14)0.0009 (13)0.0141 (14)
Geometric parameters (Å, º) top
Sn1—O12.0930 (17)Sn2—O412.0966 (17)
Sn1—O22.6051 (18)Sn2—O422.5613 (19)
Sn1—O42.0872 (17)Sn2—O442.0855 (19)
Sn1—O52.6517 (18)Sn2—O452.6798 (19)
Sn1—C292.089 (3)Sn2—C692.093 (3)
Sn1—C302.090 (3)Sn2—C702.095 (3)
O1—C11.294 (3)O41—C411.302 (3)
O2—C11.258 (3)O42—C411.250 (3)
O3—C31.355 (3)O43—C431.348 (3)
O3—H30.80 (4)O43—H430.72 (3)
O4—C141.302 (3)O44—C541.292 (3)
O5—C141.251 (3)O45—C541.261 (3)
O6—C161.348 (3)O46—C561.346 (3)
O6—H60.75 (3)O46—H460.84 (3)
N1—N21.261 (3)N41—N421.262 (3)
N1—C61.423 (3)N41—C461.423 (3)
N2—C81.422 (3)N42—C481.423 (3)
N3—N41.261 (3)N43—N441.256 (3)
N3—C191.423 (3)N43—C591.424 (3)
N4—C211.427 (3)N44—C611.424 (3)
C1—C21.474 (4)C41—C421.472 (4)
C2—C71.393 (4)C42—C471.395 (4)
C2—C31.397 (4)C42—C431.402 (4)
C3—C41.401 (4)C43—C441.397 (4)
C4—C51.372 (4)C44—C451.381 (4)
C4—H40.9500C44—H440.9500
C5—C61.396 (4)C45—C461.402 (4)
C5—H50.9500C45—H450.9500
C6—C71.388 (4)C46—C471.375 (4)
C7—H70.9500C47—H470.9500
C8—C131.385 (4)C48—C531.388 (4)
C8—C91.390 (4)C48—C491.401 (4)
C9—C101.381 (4)C49—C501.384 (4)
C9—H90.9500C49—H490.9500
C10—C111.398 (4)C50—C511.399 (4)
C10—H100.9500C50—H500.9500
C11—C121.390 (4)C51—C521.380 (4)
C11—C271.512 (4)C51—C671.517 (4)
C12—C131.389 (4)C52—C531.384 (4)
C12—H120.9500C52—H520.9500
C13—H130.9500C53—H530.9500
C14—C151.463 (4)C54—C551.468 (4)
C15—C201.396 (4)C55—C601.392 (4)
C15—C161.411 (4)C55—C561.407 (4)
C16—C171.390 (4)C56—C571.399 (4)
C17—C181.372 (4)C57—C581.369 (4)
C17—H170.9500C57—H570.9500
C18—C191.402 (4)C58—C591.406 (4)
C18—H180.9500C58—H580.9500
C19—C201.382 (4)C59—C601.382 (4)
C20—H200.9500C60—H600.9500
C21—C221.375 (4)C61—C661.381 (4)
C21—C261.385 (4)C61—C621.389 (4)
C22—C231.379 (4)C62—C631.371 (4)
C22—H220.9500C62—H620.9500
C23—C241.389 (4)C63—C641.394 (4)
C23—H230.9500C63—H630.9500
C24—C251.377 (4)C64—C651.383 (4)
C24—C281.510 (4)C64—C681.510 (4)
C25—C261.385 (4)C65—C661.387 (4)
C25—H250.9500C65—H650.9500
C26—H260.9500C66—H660.9500
C27—H2710.9800C67—H6710.9800
C27—H2720.9800C67—H6720.9800
C27—H2730.9800C67—H6730.9800
C28—H2810.9800C68—H6810.9800
C28—H2820.9800C68—H6820.9800
C28—H2830.9800C68—H6830.9800
C29—H2910.9800C69—H6910.9800
C29—H2920.9800C69—H6920.9800
C29—H2930.9800C69—H6930.9800
C30—H3010.9800C70—H7010.9800
C30—H3020.9800C70—H7020.9800
C30—H3030.9800C70—H7030.9800
O1—Sn1—O482.93 (7)O41—Sn2—O4483.06 (7)
O1—Sn1—O5136.76 (6)O41—Sn2—O45136.67 (7)
O1—Sn1—C29104.91 (10)O41—Sn2—C69107.65 (10)
O1—Sn1—C30107.95 (10)O41—Sn2—C70105.62 (10)
O2—Sn1—O4137.49 (7)O42—Sn2—O44138.31 (6)
O2—Sn1—O5168.41 (6)O42—Sn2—O45168.07 (6)
O2—Sn1—C2986.97 (10)O42—Sn2—C6990.91 (10)
O2—Sn1—C3089.97 (10)O42—Sn2—C7089.12 (9)
O4—Sn1—C29105.62 (11)O44—Sn2—C69103.72 (11)
O4—Sn1—C30105.34 (10)O44—Sn2—C70103.02 (10)
O5—Sn1—C2986.87 (10)O45—Sn2—C6984.44 (10)
O5—Sn1—C3087.83 (10)O45—Sn2—C7087.28 (9)
C29—Sn1—C30136.93 (12)C69—Sn2—C70139.25 (12)
O1—Sn1—O254.57 (6)O41—Sn2—O4255.25 (6)
O4—Sn1—O553.89 (6)O44—Sn2—O4553.62 (6)
C1—O1—Sn1104.55 (16)C41—O41—Sn2102.78 (16)
C1—O2—Sn181.64 (15)C41—O42—Sn282.61 (16)
C3—O3—H3105 (3)C43—O43—H43109 (3)
C14—O4—Sn1105.80 (16)C54—O44—Sn2106.52 (17)
C14—O5—Sn180.75 (15)C54—O45—Sn279.59 (16)
C16—O6—H6113 (3)C56—O46—H46109 (2)
N2—N1—C6113.8 (2)N42—N41—C46114.2 (2)
N1—N2—C8114.3 (2)N41—N42—C48114.3 (2)
N4—N3—C19113.9 (2)N44—N43—C59114.0 (2)
N3—N4—C21114.5 (2)N43—N44—C61114.2 (2)
O2—C1—O1119.2 (2)O42—C41—O41119.0 (2)
O2—C1—C2121.9 (2)O42—C41—C42122.4 (3)
O1—C1—C2118.9 (2)O41—C41—C42118.5 (2)
C7—C2—C3119.1 (3)C47—C42—C43118.8 (3)
C7—C2—C1120.7 (2)C47—C42—C41120.7 (2)
C3—C2—C1120.2 (2)C43—C42—C41120.4 (2)
O3—C3—C2123.2 (3)O43—C43—C44116.7 (3)
O3—C3—C4116.7 (3)O43—C43—C42123.4 (3)
C2—C3—C4120.1 (3)C44—C43—C42119.9 (3)
C5—C4—C3120.0 (3)C45—C44—C43119.9 (3)
C5—C4—H4120.0C45—C44—H44120.0
C3—C4—H4120.0C43—C44—H44120.0
C4—C5—C6120.6 (3)C44—C45—C46120.7 (3)
C4—C5—H5119.7C44—C45—H45119.6
C6—C5—H5119.7C46—C45—H45119.6
C7—C6—C5119.4 (3)C47—C46—C45118.9 (3)
C7—C6—N1116.1 (2)C47—C46—N41116.6 (2)
C5—C6—N1124.6 (3)C45—C46—N41124.5 (3)
C6—C7—C2120.8 (3)C46—C47—C42121.7 (3)
C6—C7—H7119.6C46—C47—H47119.2
C2—C7—H7119.6C42—C47—H47119.2
C13—C8—C9119.6 (3)C53—C48—C49119.1 (3)
C13—C8—N2115.8 (3)C53—C48—N42116.1 (3)
C9—C8—N2124.6 (3)C49—C48—N42124.8 (3)
C10—C9—C8120.0 (3)C50—C49—C48120.2 (3)
C10—C9—H9120.0C50—C49—H49119.9
C8—C9—H9120.0C48—C49—H49119.9
C9—C10—C11121.1 (3)C49—C50—C51120.6 (3)
C9—C10—H10119.5C49—C50—H50119.7
C11—C10—H10119.5C51—C50—H50119.7
C12—C11—C10118.4 (3)C52—C51—C50118.5 (3)
C12—C11—C27120.5 (3)C52—C51—C67122.0 (3)
C10—C11—C27121.1 (3)C50—C51—C67119.5 (3)
C13—C12—C11120.6 (3)C51—C52—C53121.5 (3)
C13—C12—H12119.7C51—C52—H52119.2
C11—C12—H12119.7C53—C52—H52119.2
C8—C13—C12120.3 (3)C52—C53—C48120.0 (3)
C8—C13—H13119.9C52—C53—H53120.0
C12—C13—H13119.9C48—C53—H53120.0
O5—C14—O4119.5 (2)O45—C54—O44120.3 (3)
O5—C14—C15122.5 (2)O45—C54—C55122.1 (3)
O4—C14—C15118.0 (2)O44—C54—C55117.7 (2)
C20—C15—C16118.7 (2)C60—C55—C56118.8 (3)
C20—C15—C14120.6 (2)C60—C55—C54120.4 (3)
C16—C15—C14120.8 (2)C56—C55—C54120.7 (2)
O6—C16—C17117.9 (2)O46—C56—C57118.2 (3)
O6—C16—C15122.4 (2)O46—C56—C55122.3 (3)
C17—C16—C15119.6 (3)C57—C56—C55119.5 (3)
C18—C17—C16120.7 (3)C58—C57—C56120.7 (3)
C18—C17—H17119.6C58—C57—H57119.6
C16—C17—H17119.6C56—C57—H57119.6
C17—C18—C19120.5 (3)C57—C58—C59120.4 (3)
C17—C18—H18119.7C57—C58—H58119.8
C19—C18—H18119.7C59—C58—H58119.8
C20—C19—C18119.0 (3)C60—C59—C58118.8 (3)
C20—C19—N3116.3 (2)C60—C59—N43116.3 (2)
C18—C19—N3124.7 (2)C58—C59—N43124.9 (3)
C19—C20—C15121.4 (2)C59—C60—C55121.6 (3)
C19—C20—H20119.3C59—C60—H60119.2
C15—C20—H20119.3C55—C60—H60119.2
C22—C21—C26119.2 (3)C66—C61—C62119.7 (3)
C22—C21—N4125.4 (2)C66—C61—N44115.8 (3)
C26—C21—N4115.4 (2)C62—C61—N44124.6 (3)
C21—C22—C23120.2 (3)C63—C62—C61119.8 (3)
C21—C22—H22119.9C63—C62—H62120.1
C23—C22—H22119.9C61—C62—H62120.1
C22—C23—C24121.4 (3)C62—C63—C64121.6 (3)
C22—C23—H23119.3C62—C63—H63119.2
C24—C23—H23119.3C64—C63—H63119.2
C25—C24—C23117.9 (3)C65—C64—C63117.8 (3)
C25—C24—C28121.7 (3)C65—C64—C68121.0 (3)
C23—C24—C28120.4 (3)C63—C64—C68121.2 (3)
C24—C25—C26121.2 (3)C64—C65—C66121.3 (3)
C24—C25—H25119.4C64—C65—H65119.3
C26—C25—H25119.4C66—C65—H65119.3
C21—C26—C25120.1 (3)C61—C66—C65119.8 (3)
C21—C26—H26119.9C61—C66—H66120.1
C25—C26—H26119.9C65—C66—H66120.1
C11—C27—H271109.5C51—C67—H671109.5
C11—C27—H272109.5C51—C67—H672109.5
H271—C27—H272109.5H671—C67—H672109.5
C11—C27—H273109.5C51—C67—H673109.5
H271—C27—H273109.5H671—C67—H673109.5
H272—C27—H273109.5H672—C67—H673109.5
C24—C28—H281109.5C64—C68—H681109.5
C24—C28—H282109.5C64—C68—H682109.5
H281—C28—H282109.5H681—C68—H682109.5
C24—C28—H283109.5C64—C68—H683109.5
H281—C28—H283109.5H681—C68—H683109.5
H282—C28—H283109.5H682—C68—H683109.5
Sn1—C29—H291109.5Sn2—C69—H691109.5
Sn1—C29—H292109.5Sn2—C69—H692109.5
H291—C29—H292109.5H691—C69—H692109.5
Sn1—C29—H293109.5Sn2—C69—H693109.5
H291—C29—H293109.5H691—C69—H693109.5
H292—C29—H293109.5H692—C69—H693109.5
Sn1—C30—H301109.5Sn2—C70—H701109.5
Sn1—C30—H302109.5Sn2—C70—H702109.5
H301—C30—H302109.5H701—C70—H702109.5
Sn1—C30—H303109.5Sn2—C70—H703109.5
H301—C30—H303109.5H701—C70—H703109.5
H302—C30—H303109.5H702—C70—H703109.5
C6—N1—N2—C8179.6 (2)C46—N41—N42—C48179.2 (2)
C19—N3—N4—C21178.0 (2)C59—N43—N44—C61177.4 (2)
Sn1—O2—C1—O12.1 (2)Sn2—O42—C41—O415.3 (2)
Sn1—O2—C1—C2176.6 (3)Sn2—O42—C41—C42172.6 (3)
Sn1—O1—C1—O22.7 (3)Sn2—O41—C41—O426.6 (3)
Sn1—O1—C1—C2176.1 (2)Sn2—O41—C41—C42171.4 (2)
O2—C1—C2—C7178.5 (3)O42—C41—C42—C47174.7 (3)
O1—C1—C2—C70.2 (4)O41—C41—C42—C473.1 (4)
O2—C1—C2—C30.1 (4)O42—C41—C42—C433.7 (4)
O1—C1—C2—C3178.6 (3)O41—C41—C42—C43178.4 (2)
C7—C2—C3—O3178.6 (3)C47—C42—C43—O43179.2 (3)
C1—C2—C3—O30.3 (4)C41—C42—C43—O432.3 (4)
C7—C2—C3—C40.5 (4)C47—C42—C43—C440.5 (4)
C1—C2—C3—C4177.9 (3)C41—C42—C43—C44177.9 (3)
O3—C3—C4—C5179.3 (3)O43—C43—C44—C45179.1 (3)
C2—C3—C4—C51.0 (4)C42—C43—C44—C450.7 (4)
C3—C4—C5—C60.4 (4)C43—C44—C45—C460.6 (4)
C4—C5—C6—C70.7 (4)C44—C45—C46—C470.3 (4)
C4—C5—C6—N1179.6 (3)C44—C45—C46—N41179.5 (3)
N2—N1—C6—C7173.6 (2)N42—N41—C46—C47172.7 (2)
N2—N1—C6—C57.5 (4)N42—N41—C46—C457.2 (4)
C5—C6—C7—C21.3 (4)C45—C46—C47—C420.2 (4)
N1—C6—C7—C2179.7 (3)N41—C46—C47—C42179.7 (2)
C3—C2—C7—C60.7 (4)C43—C42—C47—C460.3 (4)
C1—C2—C7—C6179.0 (3)C41—C42—C47—C46178.2 (3)
N1—N2—C8—C13176.6 (3)N41—N42—C48—C53175.5 (2)
N1—N2—C8—C94.6 (4)N41—N42—C48—C495.3 (4)
C13—C8—C9—C102.4 (5)C53—C48—C49—C501.8 (4)
N2—C8—C9—C10178.8 (3)N42—C48—C49—C50179.0 (3)
C8—C9—C10—C110.9 (5)C48—C49—C50—C510.1 (5)
C9—C10—C11—C120.9 (5)C49—C50—C51—C520.6 (5)
C9—C10—C11—C27179.3 (3)C49—C50—C51—C67178.1 (3)
C10—C11—C12—C131.2 (5)C50—C51—C52—C530.5 (4)
C27—C11—C12—C13179.0 (3)C67—C51—C52—C53179.2 (3)
C9—C8—C13—C122.1 (5)C51—C52—C53—C482.3 (4)
N2—C8—C13—C12179.0 (3)C49—C48—C53—C522.9 (4)
C11—C12—C13—C80.3 (5)N42—C48—C53—C52177.8 (3)
Sn1—O5—C14—O42.5 (2)Sn2—O45—C54—O440.8 (2)
Sn1—O5—C14—C15176.8 (3)Sn2—O45—C54—C55178.9 (3)
Sn1—O4—C14—O53.3 (3)Sn2—O44—C54—O451.1 (3)
Sn1—O4—C14—C15176.1 (2)Sn2—O44—C54—C55178.6 (2)
O5—C14—C15—C20175.0 (3)O45—C54—C55—C60175.8 (3)
O4—C14—C15—C204.4 (4)O44—C54—C55—C604.5 (4)
O5—C14—C15—C165.8 (4)O45—C54—C55—C565.5 (4)
O4—C14—C15—C16174.8 (3)O44—C54—C55—C56174.2 (2)
C20—C15—C16—O6178.3 (3)C60—C55—C56—O46178.9 (3)
C14—C15—C16—O61.0 (4)C54—C55—C56—O462.5 (4)
C20—C15—C16—C171.1 (4)C60—C55—C56—C572.6 (4)
C14—C15—C16—C17179.6 (3)C54—C55—C56—C57176.1 (3)
O6—C16—C17—C18178.7 (3)O46—C56—C57—C58178.8 (3)
C15—C16—C17—C180.7 (4)C55—C56—C57—C582.6 (4)
C16—C17—C18—C190.5 (4)C56—C57—C58—C590.5 (4)
C17—C18—C19—C200.9 (4)C57—C58—C59—C601.7 (4)
C17—C18—C19—N3178.4 (3)C57—C58—C59—N43177.7 (3)
N4—N3—C19—C20168.4 (3)N44—N43—C59—C60175.9 (2)
N4—N3—C19—C1814.0 (4)N44—N43—C59—C584.6 (4)
C18—C19—C20—C151.4 (4)C58—C59—C60—C551.7 (4)
N3—C19—C20—C15179.1 (2)N43—C59—C60—C55177.7 (2)
C16—C15—C20—C191.5 (4)C56—C55—C60—C590.4 (4)
C14—C15—C20—C19179.2 (3)C54—C55—C60—C59178.3 (3)
N3—N4—C21—C229.6 (4)N43—N44—C61—C66166.8 (3)
N3—N4—C21—C26172.1 (3)N43—N44—C61—C6214.1 (4)
C26—C21—C22—C230.1 (5)C66—C61—C62—C631.2 (4)
N4—C21—C22—C23178.2 (3)N44—C61—C62—C63179.7 (3)
C21—C22—C23—C240.1 (5)C61—C62—C63—C640.1 (5)
C22—C23—C24—C250.1 (5)C62—C63—C64—C651.7 (5)
C22—C23—C24—C28180.0 (3)C62—C63—C64—C68178.3 (3)
C23—C24—C25—C260.3 (5)C63—C64—C65—C661.9 (5)
C28—C24—C25—C26179.7 (3)C68—C64—C65—C66178.1 (3)
C22—C21—C26—C250.4 (5)C62—C61—C66—C651.0 (5)
N4—C21—C26—C25178.1 (3)N44—C61—C66—C65179.9 (3)
C24—C25—C26—C210.5 (5)C64—C65—C66—C610.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.80 (4)1.89 (4)2.611 (3)150 (4)
O6—H6···O50.75 (3)2.00 (3)2.634 (3)142 (4)
O6—H6···O420.75 (3)2.35 (3)2.887 (3)130 (3)
O43—H43···O50.72 (3)2.62 (3)3.151 (3)132 (3)
O43—H43···O420.72 (3)2.01 (3)2.642 (3)146 (4)
O46—H46···O450.84 (3)1.89 (3)2.618 (3)145 (3)
C29—H292···O430.982.373.314 (4)162
C30—H303···O46i0.982.583.357 (4)136
C68—H681···O44ii0.982.563.463 (4)153
C69—H691···O2iii0.982.553.443 (4)151
C12—H12···Cg7iv0.953.003.833 (3)147
C68—H683···Cg5v0.982.863.625 (3)136
Symmetry codes: (i) x+1, y, z; (ii) x2, y1, z; (iii) x1, y, z; (iv) x, y+1, z+1; (v) x1, y1, 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]·0.5C6H6F(000) = 1612
Mr = 1564.92Dx = 1.447 Mg m3
Triclinic, P1Melting point: 448 K
a = 12.0462 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.6264 (2) ÅCell parameters from 87809 reflections
c = 22.8143 (3) Åθ = 2.0–27.5°
α = 102.2665 (6)°µ = 0.76 mm1
β = 100.3180 (6)°T = 160 K
γ = 91.6029 (6)°Prism, orange
V = 3591.71 (8) Å30.23 × 0.18 × 0.18 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
16442 independent reflections
Radiation source: Nonius FR590 sealed tube generator10227 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.083
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.1°
φ and ω scans with κ offsetsh = 1515
Absorption correction: multi-scan
(Blessing, 1995)
k = 1717
Tmin = 0.802, Tmax = 0.881l = 2929
76914 measured reflections
Refinement top
Refinement on F2181 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-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 reflectionsΔρmax = 1.58 e Å3
971 parametersΔρmin = 0.95 e Å3
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
xyzUiso*/UeqOcc. (<1)
Sn10.44920 (2)0.59909 (2)0.09762 (2)0.03200 (8)
O10.33833 (19)0.50947 (16)0.02250 (10)0.0353 (6)
O20.2592 (2)0.65266 (16)0.04583 (11)0.0388 (6)
O30.0608 (2)0.67716 (17)0.01607 (12)0.0443 (6)
H30.11910.69340.01120.066*
O40.5435 (2)0.47234 (16)0.08918 (11)0.0366 (6)
O50.6404 (2)0.58034 (17)0.16900 (11)0.0407 (6)
O60.8167 (2)0.52092 (17)0.23536 (12)0.0449 (6)
H60.77130.56220.22440.067*
N10.0642 (2)0.2813 (2)0.14326 (13)0.0339 (7)
N20.0197 (2)0.2482 (2)0.18465 (13)0.0341 (7)
N30.7190 (3)0.1484 (2)0.07225 (14)0.0388 (7)
N40.7796 (3)0.0789 (2)0.08239 (14)0.0422 (8)
C10.2547 (3)0.5647 (2)0.01351 (15)0.0331 (8)
C20.1560 (3)0.5229 (2)0.03385 (15)0.0280 (8)
C30.0640 (3)0.5815 (2)0.04607 (16)0.0342 (8)
C40.0290 (3)0.5392 (3)0.09142 (17)0.0407 (9)
H40.09110.57870.10010.049*
C50.0321 (3)0.4414 (3)0.12360 (16)0.0358 (8)
H50.09650.41350.15390.043*
C60.0595 (3)0.3827 (2)0.11182 (15)0.0304 (8)
C70.1516 (3)0.4234 (2)0.06746 (15)0.0294 (8)
H70.21350.38350.05940.035*
C80.0168 (3)0.1460 (2)0.21532 (15)0.0316 (8)
C90.0705 (3)0.0847 (3)0.20264 (16)0.0389 (9)
H90.13490.11060.17190.047*
C100.0632 (3)0.0138 (3)0.23479 (17)0.0420 (9)
H100.12330.05530.22600.050*
C110.0298 (3)0.0535 (3)0.27958 (17)0.0405 (9)
C120.1157 (3)0.0084 (3)0.29292 (17)0.0455 (10)
H120.17950.01720.32410.055*
C130.1088 (3)0.1083 (3)0.26073 (16)0.0408 (9)
H130.16780.15040.27020.049*
C140.6276 (3)0.4939 (2)0.13494 (16)0.0320 (8)
C150.7035 (3)0.4144 (2)0.14517 (15)0.0307 (8)
C160.7921 (3)0.4304 (2)0.19580 (16)0.0332 (8)
C170.8572 (3)0.3515 (3)0.20698 (17)0.0397 (9)
H170.91590.36190.24200.048*
C180.8375 (3)0.2579 (3)0.16750 (17)0.0401 (9)
H180.88330.20470.17510.048*
C190.7500 (3)0.2417 (2)0.11650 (16)0.0330 (8)
C200.6835 (3)0.3192 (2)0.10639 (16)0.0330 (8)
H200.62270.30750.07230.040*
C210.7465 (3)0.0141 (3)0.03794 (16)0.0359 (9)
C220.6494 (3)0.0296 (3)0.00670 (18)0.0455 (10)
H220.60040.02320.01000.055*
C230.6240 (3)0.1234 (3)0.04675 (17)0.0438 (9)
H230.55710.13440.07720.053*
C240.6955 (3)0.2008 (3)0.04261 (17)0.0377 (9)
C250.7919 (3)0.1834 (3)0.00258 (17)0.0447 (10)
H250.84160.23570.00590.054*
C260.8166 (3)0.0916 (3)0.04264 (17)0.0448 (10)
H260.88240.08140.07380.054*
C270.0388 (4)0.1633 (3)0.31433 (19)0.0546 (12)
H2710.03650.18940.31040.082*
H2720.07020.16770.35760.082*
H2730.08850.20330.29730.082*
C280.6685 (3)0.3021 (3)0.08653 (18)0.0496 (11)
H2810.58830.32260.09110.074*
H2820.71480.35210.07060.074*
H2830.68510.29720.12640.074*
C290.3650 (3)0.5830 (3)0.16937 (17)0.0433 (10)
H2910.29000.54750.15090.052*
H2920.40850.53900.19310.052*
C300.3475 (4)0.6780 (3)0.21331 (18)0.0596 (12)
H3010.29000.66380.23700.072*
H3020.31900.72890.19020.072*
C310.4590 (4)0.7200 (4)0.2574 (2)0.0743 (15)
H3110.48580.66970.28130.089*
H3120.51710.73140.23340.089*
C320.4460 (4)0.8152 (4)0.2996 (2)0.0817 (16)
H3210.41850.86500.27620.123*
H3220.51920.84030.32590.123*
H3230.39150.80350.32500.123*
C330.5362 (3)0.7035 (2)0.06225 (16)0.0410 (9)
H3310.59540.66810.04270.049*0.718 (6)
H3320.48200.72390.02970.049*0.718 (6)
H3330.61740.70670.08100.049*0.282 (6)
H3340.52980.67620.01790.049*0.282 (6)
C34A0.5916 (5)0.7974 (3)0.1063 (2)0.0485 (15)0.718 (6)
H3410.64100.83210.08560.058*0.718 (6)
H3420.64050.77780.14110.058*0.718 (6)
C35A0.5106 (6)0.8710 (7)0.1310 (4)0.067 (2)0.718 (6)
H3510.46030.88990.09640.081*0.718 (6)
H3520.46280.83770.15320.081*0.718 (6)
C36A0.5708 (7)0.9646 (5)0.1734 (3)0.079 (2)0.718 (6)
H3610.51531.00760.19050.118*0.718 (6)
H3620.61271.00120.15060.118*0.718 (6)
H3630.62360.94610.20660.118*0.718 (6)
C34B0.4994 (11)0.8094 (5)0.0710 (6)0.044 (2)0.282 (6)
H3430.42590.80880.04330.053*0.282 (6)
H3440.55500.85130.05820.053*0.282 (6)
C35B0.4865 (14)0.860 (2)0.1356 (8)0.061 (4)0.282 (6)
H3530.43610.91600.13380.073*0.282 (6)
H3540.45120.81090.15410.073*0.282 (6)
C36B0.5992 (16)0.9004 (17)0.1745 (7)0.089 (5)0.282 (6)
H3640.64160.93670.15190.134*0.282 (6)
H3650.64180.84440.18510.134*0.282 (6)
H3660.58770.94630.21200.134*0.282 (6)
Sn20.59619 (2)0.66771 (2)0.49220 (2)0.02954 (8)
O410.6835 (2)0.53667 (16)0.48649 (11)0.0362 (6)
O420.79209 (19)0.64877 (15)0.55971 (10)0.0342 (5)
O430.9810 (2)0.59333 (17)0.61777 (11)0.0403 (6)
H430.93200.63350.60940.061*
O440.48199 (19)0.57754 (16)0.41943 (11)0.0387 (6)
O450.40301 (19)0.72170 (16)0.43866 (10)0.0346 (6)
O460.2034 (2)0.74147 (16)0.37532 (11)0.0370 (6)
H460.25490.75570.40650.056*
N410.8703 (2)0.2176 (2)0.46087 (13)0.0333 (7)
N420.9407 (2)0.1516 (2)0.46245 (13)0.0339 (7)
N430.2245 (3)0.3468 (2)0.24958 (13)0.0376 (7)
N440.1498 (2)0.3132 (2)0.20366 (13)0.0336 (7)
C410.7749 (3)0.5608 (2)0.52757 (15)0.0288 (8)
C420.8542 (3)0.4826 (2)0.53486 (15)0.0272 (7)
C430.9531 (3)0.5030 (2)0.57958 (16)0.0310 (8)
C441.0267 (3)0.4255 (2)0.58553 (17)0.0372 (9)
H441.09340.43800.61610.045*
C451.0024 (3)0.3323 (3)0.54739 (16)0.0345 (8)
H451.05300.28090.55160.041*
C460.9052 (3)0.3117 (2)0.50278 (15)0.0296 (8)
C470.8311 (3)0.3864 (2)0.49697 (15)0.0279 (7)
H470.76380.37220.46690.033*
C480.9028 (3)0.0582 (2)0.42035 (16)0.0322 (8)
C490.7972 (3)0.0381 (3)0.38221 (17)0.0373 (9)
H490.74430.08860.38270.045*
C500.7699 (3)0.0548 (3)0.34394 (17)0.0396 (9)
H500.69760.06800.31810.048*
C510.8457 (3)0.1309 (3)0.34199 (17)0.0394 (9)
C520.9500 (3)0.1095 (2)0.37948 (17)0.0382 (9)
H521.00310.15980.37840.046*
C530.9797 (3)0.0162 (2)0.41902 (16)0.0353 (8)
H531.05200.00320.44490.042*
C540.3990 (3)0.6328 (2)0.40817 (15)0.0298 (8)
C550.3032 (3)0.5893 (2)0.35965 (15)0.0283 (7)
C560.2098 (3)0.6457 (2)0.34531 (15)0.0282 (8)
C570.1204 (3)0.6022 (2)0.29813 (15)0.0322 (8)
H570.05730.64020.28870.039*
C580.1218 (3)0.5055 (2)0.26506 (15)0.0320 (8)
H580.06070.47730.23270.038*
C590.2141 (3)0.4491 (2)0.27952 (15)0.0305 (8)
C600.3028 (3)0.4905 (2)0.32604 (15)0.0327 (8)
H600.36480.45140.33550.039*
C610.1580 (3)0.2091 (2)0.17527 (15)0.0323 (8)
C620.2366 (3)0.1480 (3)0.19879 (17)0.0424 (9)
H620.29080.17420.23490.051*
C630.2345 (3)0.0484 (3)0.16858 (17)0.0458 (10)
H630.28730.00620.18500.055*
C640.1587 (3)0.0082 (3)0.11554 (17)0.0412 (10)
C650.0818 (3)0.0715 (3)0.09272 (17)0.0421 (9)
H650.02840.04560.05620.051*
C660.0816 (3)0.1710 (3)0.12207 (16)0.0392 (9)
H660.02880.21310.10560.047*
C670.8131 (3)0.2332 (3)0.29954 (17)0.0456 (10)
H6710.73880.25800.30430.068*
H6720.86950.28040.30970.068*
H6730.80990.22730.25720.068*
C680.1583 (4)0.1011 (3)0.08387 (18)0.0505 (11)
H6810.09410.11780.04950.076*
H6820.15150.14370.11290.076*
H6830.22900.11280.06870.076*
C690.6876 (3)0.7558 (2)0.44813 (16)0.0354 (8)
H6910.75160.71790.43570.042*
H6920.63740.76450.41050.042*
C700.7342 (3)0.8596 (2)0.48601 (17)0.0377 (9)
H7010.77350.85290.52680.045*
H7020.79050.88720.46600.045*
C710.6423 (3)0.9328 (3)0.49370 (18)0.0428 (10)
H7110.60450.94100.45290.051*
H7120.58490.90430.51260.051*
C720.6880 (3)1.0353 (3)0.53290 (19)0.0496 (11)
H7210.72481.02770.57350.074*
H7220.62551.07930.53680.074*
H7230.74311.06490.51370.074*
C730.5172 (3)0.6722 (3)0.56841 (16)0.0406 (9)
H7310.44050.69570.55870.049*0.459 (5)
H7320.50840.60270.57440.049*0.459 (5)
H7330.44880.62510.55560.049*0.541 (5)
H7340.56950.64780.60010.049*0.541 (5)
C74A0.5793 (6)0.7393 (4)0.6286 (3)0.0426 (18)0.459 (5)
H7410.53280.73670.66000.051*0.459 (5)
H7420.65100.70900.64100.051*0.459 (5)
C75A0.6075 (8)0.8498 (6)0.6303 (10)0.045 (3)0.459 (5)
H7510.65510.88150.67030.055*0.459 (5)
H7520.65160.85440.59820.055*0.459 (5)
C76A0.5026 (8)0.9061 (6)0.6205 (5)0.056 (3)0.459 (5)
H7610.45830.90100.65200.084*0.459 (5)
H7620.45720.87700.58010.084*0.459 (5)
H7630.52410.97710.62320.084*0.459 (5)
C74B0.4838 (5)0.7743 (4)0.5961 (3)0.0401 (17)0.541 (5)
H7430.42730.76790.62190.048*0.541 (5)
H7440.44990.80810.56350.048*0.541 (5)
C75B0.5896 (7)0.8355 (6)0.6347 (8)0.047 (2)0.541 (5)
H7530.62600.79880.66530.056*0.541 (5)
H7540.64400.84460.60820.056*0.541 (5)
C76B0.5598 (7)0.9374 (5)0.6671 (4)0.064 (2)0.541 (5)
H7640.62830.97480.69280.097*0.541 (5)
H7650.50470.92830.69260.097*0.541 (5)
H7660.52710.97500.63670.097*0.541 (5)
C800.5366 (4)0.3454 (4)0.2498 (2)0.0760 (14)
H800.47100.36210.22490.091*
C810.5734 (4)0.2499 (4)0.2372 (2)0.0677 (14)
H810.53280.20100.20360.081*
C820.6672 (4)0.2246 (4)0.2721 (2)0.0676 (13)
H820.69250.15860.26340.081*
C830.7251 (4)0.2975 (4)0.3207 (2)0.0713 (14)
H830.79180.28190.34520.086*
C840.6871 (4)0.3912 (4)0.3336 (2)0.0668 (13)
H840.72620.43990.36780.080*
C850.5940 (5)0.4159 (4)0.2980 (2)0.0698 (14)
H850.56900.48210.30670.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03061 (15)0.02481 (14)0.03640 (16)0.00053 (10)0.00358 (12)0.00003 (11)
O10.0303 (14)0.0280 (13)0.0403 (14)0.0043 (11)0.0027 (11)0.0006 (11)
O20.0418 (15)0.0269 (13)0.0416 (15)0.0031 (11)0.0024 (12)0.0015 (11)
O30.0473 (17)0.0305 (14)0.0464 (17)0.0129 (12)0.0012 (13)0.0033 (12)
O40.0371 (15)0.0272 (13)0.0403 (15)0.0031 (11)0.0005 (12)0.0027 (11)
O50.0386 (15)0.0286 (13)0.0499 (16)0.0048 (11)0.0071 (13)0.0019 (12)
O60.0409 (16)0.0276 (14)0.0533 (17)0.0008 (12)0.0076 (13)0.0051 (12)
N10.0354 (18)0.0296 (16)0.0348 (17)0.0001 (14)0.0026 (15)0.0063 (13)
N20.0372 (18)0.0307 (16)0.0321 (17)0.0008 (14)0.0042 (15)0.0042 (13)
N30.044 (2)0.0290 (16)0.0454 (19)0.0085 (15)0.0142 (16)0.0081 (14)
N40.043 (2)0.0366 (18)0.045 (2)0.0013 (16)0.0058 (16)0.0085 (15)
C10.037 (2)0.0274 (19)0.035 (2)0.0019 (16)0.0097 (17)0.0052 (16)
C20.0279 (19)0.0259 (18)0.0285 (19)0.0008 (15)0.0052 (16)0.0028 (14)
C30.043 (2)0.0247 (18)0.033 (2)0.0093 (17)0.0064 (18)0.0025 (15)
C40.037 (2)0.039 (2)0.043 (2)0.0139 (18)0.0005 (19)0.0065 (18)
C50.033 (2)0.037 (2)0.033 (2)0.0042 (17)0.0008 (17)0.0041 (16)
C60.033 (2)0.0244 (18)0.0319 (19)0.0032 (15)0.0048 (17)0.0036 (15)
C70.0285 (19)0.0269 (18)0.0312 (19)0.0054 (15)0.0036 (16)0.0045 (15)
C80.033 (2)0.0302 (19)0.030 (2)0.0004 (16)0.0042 (16)0.0047 (16)
C90.042 (2)0.035 (2)0.035 (2)0.0017 (18)0.0002 (18)0.0052 (17)
C100.052 (3)0.031 (2)0.041 (2)0.0031 (18)0.004 (2)0.0064 (17)
C110.056 (3)0.030 (2)0.038 (2)0.0021 (19)0.017 (2)0.0059 (17)
C120.046 (3)0.042 (2)0.039 (2)0.0103 (19)0.0011 (19)0.0017 (18)
C130.035 (2)0.039 (2)0.042 (2)0.0038 (17)0.0008 (18)0.0018 (18)
C140.029 (2)0.031 (2)0.036 (2)0.0006 (16)0.0081 (17)0.0053 (16)
C150.031 (2)0.0259 (18)0.036 (2)0.0026 (15)0.0115 (17)0.0040 (15)
C160.030 (2)0.0288 (19)0.038 (2)0.0023 (16)0.0062 (17)0.0005 (16)
C170.029 (2)0.038 (2)0.048 (2)0.0002 (17)0.0009 (18)0.0087 (18)
C180.035 (2)0.033 (2)0.055 (3)0.0099 (17)0.012 (2)0.0128 (18)
C190.039 (2)0.0269 (19)0.036 (2)0.0013 (16)0.0150 (18)0.0055 (16)
C200.035 (2)0.032 (2)0.031 (2)0.0037 (16)0.0076 (17)0.0039 (16)
C210.043 (2)0.032 (2)0.031 (2)0.0079 (17)0.0097 (18)0.0001 (16)
C220.044 (2)0.033 (2)0.059 (3)0.0062 (18)0.013 (2)0.0063 (19)
C230.040 (2)0.037 (2)0.047 (2)0.0037 (18)0.0026 (19)0.0002 (18)
C240.043 (2)0.030 (2)0.041 (2)0.0040 (17)0.016 (2)0.0051 (17)
C250.055 (3)0.033 (2)0.049 (2)0.0076 (19)0.015 (2)0.0089 (18)
C260.053 (3)0.038 (2)0.044 (2)0.0054 (19)0.010 (2)0.0069 (18)
C270.079 (3)0.032 (2)0.049 (3)0.005 (2)0.019 (2)0.0039 (18)
C280.059 (3)0.030 (2)0.060 (3)0.0074 (19)0.025 (2)0.0007 (19)
C290.039 (2)0.049 (2)0.044 (2)0.0017 (18)0.0126 (19)0.0105 (19)
C300.058 (3)0.066 (3)0.052 (3)0.010 (2)0.021 (2)0.001 (2)
C310.060 (3)0.092 (4)0.066 (3)0.011 (3)0.018 (3)0.002 (3)
C320.079 (4)0.082 (4)0.072 (4)0.016 (3)0.016 (3)0.007 (3)
C330.046 (2)0.033 (2)0.044 (2)0.0010 (17)0.0121 (19)0.0051 (17)
C34A0.054 (3)0.037 (3)0.056 (3)0.004 (2)0.019 (3)0.006 (2)
C35A0.079 (4)0.042 (4)0.082 (4)0.015 (3)0.036 (3)0.003 (3)
C36A0.104 (6)0.041 (4)0.083 (5)0.009 (4)0.026 (4)0.010 (4)
C34B0.057 (5)0.028 (4)0.055 (5)0.002 (4)0.030 (4)0.007 (4)
C35B0.081 (6)0.034 (6)0.073 (6)0.013 (6)0.034 (6)0.009 (5)
C36B0.087 (10)0.099 (10)0.083 (9)0.011 (10)0.020 (8)0.020 (9)
Sn20.02860 (14)0.01906 (13)0.03559 (15)0.00263 (10)0.00071 (11)0.00019 (10)
O410.0338 (14)0.0254 (12)0.0410 (15)0.0060 (11)0.0068 (12)0.0001 (11)
O420.0343 (14)0.0219 (12)0.0403 (14)0.0042 (10)0.0002 (11)0.0010 (11)
O430.0337 (15)0.0281 (13)0.0485 (16)0.0023 (11)0.0094 (12)0.0006 (12)
O440.0325 (14)0.0234 (12)0.0479 (15)0.0049 (11)0.0122 (12)0.0028 (11)
O450.0346 (14)0.0256 (13)0.0384 (14)0.0026 (11)0.0009 (11)0.0006 (11)
O460.0342 (15)0.0280 (13)0.0426 (16)0.0082 (11)0.0020 (12)0.0006 (11)
N410.0298 (17)0.0266 (16)0.0438 (19)0.0067 (13)0.0069 (14)0.0076 (14)
N420.0319 (17)0.0232 (15)0.0467 (19)0.0049 (13)0.0097 (15)0.0056 (13)
N430.0372 (19)0.0322 (17)0.0360 (18)0.0025 (14)0.0025 (15)0.0002 (14)
N440.0379 (18)0.0282 (16)0.0304 (17)0.0010 (13)0.0030 (14)0.0002 (13)
C410.030 (2)0.0239 (18)0.031 (2)0.0041 (15)0.0042 (16)0.0040 (15)
C420.0253 (19)0.0244 (17)0.0302 (19)0.0028 (14)0.0052 (16)0.0027 (14)
C430.030 (2)0.0251 (18)0.035 (2)0.0035 (15)0.0026 (16)0.0038 (15)
C440.029 (2)0.029 (2)0.049 (2)0.0002 (16)0.0033 (17)0.0075 (17)
C450.0238 (19)0.0311 (19)0.050 (2)0.0064 (15)0.0045 (17)0.0131 (17)
C460.031 (2)0.0243 (18)0.035 (2)0.0035 (15)0.0083 (17)0.0079 (15)
C470.0271 (19)0.0239 (17)0.0297 (19)0.0045 (14)0.0001 (15)0.0034 (14)
C480.031 (2)0.0243 (18)0.043 (2)0.0029 (15)0.0126 (18)0.0080 (16)
C490.034 (2)0.030 (2)0.048 (2)0.0101 (16)0.0073 (19)0.0069 (17)
C500.039 (2)0.031 (2)0.046 (2)0.0031 (17)0.0030 (19)0.0058 (17)
C510.050 (3)0.028 (2)0.043 (2)0.0016 (18)0.020 (2)0.0042 (17)
C520.038 (2)0.0266 (19)0.053 (2)0.0090 (17)0.017 (2)0.0053 (17)
C530.030 (2)0.0298 (19)0.046 (2)0.0052 (16)0.0108 (18)0.0058 (17)
C540.030 (2)0.0244 (18)0.033 (2)0.0009 (15)0.0035 (16)0.0037 (15)
C550.0294 (19)0.0271 (18)0.0270 (19)0.0018 (15)0.0021 (15)0.0059 (14)
C560.0285 (19)0.0251 (18)0.0304 (19)0.0013 (15)0.0080 (16)0.0028 (15)
C570.0252 (19)0.034 (2)0.035 (2)0.0045 (15)0.0024 (16)0.0086 (16)
C580.0259 (19)0.037 (2)0.0297 (19)0.0030 (16)0.0013 (16)0.0061 (16)
C590.035 (2)0.0251 (18)0.0287 (19)0.0011 (16)0.0021 (16)0.0033 (15)
C600.034 (2)0.0235 (18)0.036 (2)0.0025 (15)0.0009 (17)0.0016 (15)
C610.039 (2)0.0294 (19)0.0281 (19)0.0009 (16)0.0081 (17)0.0043 (15)
C620.049 (3)0.039 (2)0.033 (2)0.0007 (19)0.0024 (19)0.0007 (17)
C630.058 (3)0.032 (2)0.046 (2)0.0095 (19)0.008 (2)0.0071 (18)
C640.051 (3)0.033 (2)0.039 (2)0.0028 (19)0.017 (2)0.0006 (18)
C650.040 (2)0.038 (2)0.041 (2)0.0076 (18)0.0074 (19)0.0054 (18)
C660.034 (2)0.040 (2)0.037 (2)0.0065 (17)0.0013 (18)0.0018 (17)
C670.052 (3)0.033 (2)0.047 (2)0.0013 (19)0.013 (2)0.0019 (18)
C680.066 (3)0.030 (2)0.050 (3)0.0072 (19)0.018 (2)0.0085 (18)
C690.031 (2)0.035 (2)0.039 (2)0.0041 (16)0.0084 (17)0.0058 (17)
C700.032 (2)0.034 (2)0.047 (2)0.0016 (16)0.0093 (18)0.0071 (17)
C710.040 (2)0.032 (2)0.056 (3)0.0004 (17)0.007 (2)0.0120 (18)
C720.046 (3)0.030 (2)0.070 (3)0.0027 (18)0.012 (2)0.005 (2)
C730.040 (2)0.038 (2)0.046 (2)0.0010 (17)0.0124 (18)0.0115 (17)
C74A0.051 (4)0.032 (3)0.042 (4)0.005 (3)0.006 (3)0.005 (3)
C75A0.053 (5)0.040 (4)0.038 (5)0.003 (4)0.004 (4)0.002 (4)
C76A0.054 (6)0.048 (5)0.066 (6)0.016 (4)0.007 (5)0.018 (5)
C74B0.037 (3)0.040 (3)0.042 (3)0.001 (3)0.013 (3)0.002 (3)
C75B0.052 (4)0.051 (4)0.033 (4)0.004 (4)0.007 (4)0.002 (4)
C76B0.071 (6)0.052 (5)0.056 (5)0.003 (4)0.006 (5)0.014 (4)
C800.063 (3)0.089 (4)0.068 (4)0.007 (3)0.000 (3)0.009 (3)
C810.064 (3)0.080 (4)0.053 (3)0.017 (3)0.015 (3)0.000 (3)
C820.069 (4)0.077 (3)0.061 (3)0.008 (3)0.025 (3)0.014 (3)
C830.050 (3)0.100 (4)0.062 (3)0.003 (3)0.003 (3)0.022 (3)
C840.071 (4)0.076 (4)0.050 (3)0.020 (3)0.012 (3)0.008 (3)
C850.076 (4)0.068 (3)0.065 (3)0.000 (3)0.021 (3)0.008 (3)
Geometric parameters (Å, º) top
Sn1—O12.100 (2)O41—C411.296 (4)
Sn1—O22.581 (2)O42—C411.255 (4)
Sn1—O42.087 (2)O43—C431.343 (4)
Sn1—O52.625 (3)O43—H430.8400
Sn1—C292.119 (3)O44—C541.291 (4)
Sn1—C332.117 (3)O45—C541.257 (4)
O1—C11.287 (4)O46—C561.350 (4)
O2—C11.261 (4)O46—H460.8400
O3—C31.342 (4)N41—N421.256 (4)
O3—H30.8400N41—C461.428 (4)
O4—C141.295 (4)N42—C481.429 (4)
O5—C141.255 (4)N43—N441.246 (4)
O6—C161.354 (4)N43—C591.436 (4)
O6—H60.8400N44—C611.443 (4)
N1—N21.252 (4)C41—C421.467 (4)
N1—C61.423 (4)C42—C471.398 (4)
N2—C81.424 (4)C42—C431.401 (5)
N3—N41.247 (4)C43—C441.411 (5)
N3—C191.438 (4)C44—C451.369 (5)
N4—C211.441 (4)C44—H440.9500
C1—C21.465 (5)C45—C461.385 (5)
C2—C71.402 (4)C45—H450.9500
C2—C31.406 (5)C46—C471.385 (4)
C3—C41.397 (5)C47—H470.9500
C4—C51.375 (5)C48—C491.390 (5)
C4—H40.9500C48—C531.391 (4)
C5—C61.401 (5)C49—C501.371 (5)
C5—H50.9500C49—H490.9500
C6—C71.374 (5)C50—C511.399 (5)
C7—H70.9500C50—H500.9500
C8—C131.377 (5)C51—C521.372 (5)
C8—C91.389 (5)C51—C671.515 (5)
C9—C101.379 (5)C52—C531.390 (5)
C9—H90.9500C52—H520.9500
C10—C111.383 (5)C53—H530.9500
C10—H100.9500C54—C551.460 (5)
C11—C121.386 (5)C55—C601.400 (4)
C11—C271.528 (5)C55—C561.410 (5)
C12—C131.394 (5)C56—C571.396 (5)
C12—H120.9500C57—C581.374 (4)
C13—H130.9500C57—H570.9500
C14—C151.466 (5)C58—C591.400 (5)
C15—C201.393 (4)C58—H580.9500
C15—C161.400 (5)C59—C601.376 (5)
C16—C171.390 (5)C60—H600.9500
C17—C181.382 (5)C61—C661.376 (5)
C17—H170.9500C61—C621.390 (5)
C18—C191.397 (5)C62—C631.383 (5)
C18—H180.9500C62—H620.9500
C19—C201.377 (5)C63—C641.376 (5)
C20—H200.9500C63—H630.9500
C21—C261.380 (5)C64—C651.391 (5)
C21—C221.385 (5)C64—C681.511 (5)
C22—C231.393 (5)C65—C661.379 (5)
C22—H220.9500C65—H650.9500
C23—C241.388 (5)C66—H660.9500
C23—H230.9500C67—H6710.9800
C24—C251.386 (5)C67—H6720.9800
C24—C281.512 (5)C67—H6730.9800
C25—C261.373 (5)C68—H6810.9800
C25—H250.9500C68—H6820.9800
C26—H260.9500C68—H6830.9800
C27—H2710.9800C69—C701.525 (5)
C27—H2720.9800C69—H6910.9900
C27—H2730.9800C69—H6920.9900
C28—H2810.9800C70—C711.520 (5)
C28—H2820.9800C70—H7010.9900
C28—H2830.9800C70—H7020.9900
C29—C301.506 (5)C71—C721.517 (5)
C29—H2910.9900C71—H7110.9900
C29—H2920.9900C71—H7120.9900
C30—C311.540 (5)C72—H7210.9800
C30—H3010.9900C72—H7220.9800
C30—H3020.9900C72—H7230.9800
C31—C321.473 (5)C73—C74B1.499 (5)
C31—H3110.9900C73—C74A1.529 (5)
C31—H3120.9900C73—H7310.9900
C32—H3210.9800C73—H7320.9900
C32—H3220.9800C73—H7330.9900
C32—H3230.9800C73—H7340.9900
C33—C34A1.503 (4)C74A—C75A1.525 (8)
C33—C34B1.506 (5)C74A—H7410.9900
C33—H3310.9900C74A—H7420.9900
C33—H3320.9900C75A—C76A1.503 (8)
C33—H3330.9900C75A—H7510.9900
C33—H3340.9900C75A—H7520.9900
C34A—C35A1.512 (7)C76A—H7610.9800
C34A—H3410.9900C76A—H7620.9800
C34A—H3420.9900C76A—H7630.9800
C35A—C36A1.504 (7)C74B—C75B1.524 (8)
C35A—H3510.9900C74B—H7430.9900
C35A—H3520.9900C74B—H7440.9900
C36A—H3610.9800C75B—C76B1.512 (8)
C36A—H3620.9800C75B—H7530.9900
C36A—H3630.9800C75B—H7540.9900
C34B—C35B1.524 (9)C76B—H7640.9800
C34B—H3430.9900C76B—H7650.9800
C34B—H3440.9900C76B—H7660.9800
C35B—C36B1.500 (9)C80—C851.361 (6)
C35B—H3530.9900C80—C811.376 (6)
C35B—H3540.9900C80—H800.9500
C36B—H3640.9800C81—C821.358 (7)
C36B—H3650.9800C81—H810.9500
C36B—H3660.9800C82—C831.385 (6)
Sn2—O412.090 (2)C82—H820.9500
Sn2—O422.628 (2)C83—C841.359 (6)
Sn2—O442.093 (2)C83—H830.9500
Sn2—O452.628 (2)C84—C851.357 (6)
Sn2—C692.121 (3)C84—H840.9500
Sn2—C732.117 (3)C85—H850.9500
O1—Sn1—O483.18 (9)O44—Sn2—C73103.87 (12)
O1—Sn1—O5137.43 (8)O45—Sn2—C6991.09 (11)
O1—Sn1—C29100.36 (12)O45—Sn2—C7385.69 (11)
O1—Sn1—C33106.03 (12)C69—Sn2—C73144.09 (13)
O2—Sn1—O4138.10 (8)O44—Sn2—O4554.15 (7)
O2—Sn1—O5167.32 (7)O41—Sn2—O4254.24 (8)
O2—Sn1—C2986.01 (12)C41—O41—Sn2105.14 (19)
O2—Sn1—C3389.64 (12)C41—O42—Sn281.07 (19)
O4—Sn1—C29101.81 (12)C43—O43—H43109.5
O4—Sn1—C33104.98 (11)C54—O44—Sn2105.22 (19)
O5—Sn1—C2988.16 (12)C54—O45—Sn281.09 (19)
O5—Sn1—C3388.50 (12)C56—O46—H46109.5
C29—Sn1—C33144.16 (14)N42—N41—C46115.0 (3)
O1—Sn1—O254.94 (8)N41—N42—C48113.5 (3)
O4—Sn1—O554.28 (8)N44—N43—C59114.6 (3)
C1—O1—Sn1103.6 (2)N43—N44—C61114.3 (3)
C1—O2—Sn182.0 (2)O42—C41—O41119.5 (3)
C3—O3—H3109.5O42—C41—C42122.6 (3)
C14—O4—Sn1105.0 (2)O41—C41—C42117.9 (3)
C14—O5—Sn181.0 (2)C47—C42—C43119.4 (3)
C16—O6—H6109.5C47—C42—C41119.9 (3)
N2—N1—C6114.5 (3)C43—C42—C41120.8 (3)
N1—N2—C8114.8 (3)O43—C43—C42122.9 (3)
N4—N3—C19113.7 (3)O43—C43—C44118.1 (3)
N3—N4—C21112.9 (3)C42—C43—C44119.0 (3)
O2—C1—O1119.4 (3)C45—C44—C43120.3 (3)
O2—C1—C2121.7 (3)C45—C44—H44119.9
O1—C1—C2118.8 (3)C43—C44—H44119.9
C7—C2—C3119.0 (3)C44—C45—C46121.1 (3)
C7—C2—C1120.4 (3)C44—C45—H45119.5
C3—C2—C1120.6 (3)C46—C45—H45119.5
O3—C3—C4117.8 (3)C47—C46—C45119.4 (3)
O3—C3—C2123.1 (3)C47—C46—N41114.4 (3)
C4—C3—C2119.1 (3)C45—C46—N41126.2 (3)
C5—C4—C3121.0 (3)C46—C47—C42120.8 (3)
C5—C4—H4119.5C46—C47—H47119.6
C3—C4—H4119.5C42—C47—H47119.6
C4—C5—C6120.1 (3)C49—C48—C53119.6 (3)
C4—C5—H5119.9C49—C48—N42124.9 (3)
C6—C5—H5119.9C53—C48—N42115.5 (3)
C7—C6—C5119.5 (3)C50—C49—C48119.6 (3)
C7—C6—N1116.5 (3)C50—C49—H49120.2
C5—C6—N1124.0 (3)C48—C49—H49120.2
C6—C7—C2121.2 (3)C49—C50—C51121.8 (4)
C6—C7—H7119.4C49—C50—H50119.1
C2—C7—H7119.4C51—C50—H50119.1
C13—C8—C9119.6 (3)C52—C51—C50117.9 (3)
C13—C8—N2115.5 (3)C52—C51—C67121.4 (3)
C9—C8—N2124.9 (3)C50—C51—C67120.7 (4)
C10—C9—C8119.7 (4)C51—C52—C53121.6 (3)
C10—C9—H9120.1C51—C52—H52119.2
C8—C9—H9120.1C53—C52—H52119.2
C9—C10—C11121.3 (4)C52—C53—C48119.5 (4)
C9—C10—H10119.3C52—C53—H53120.2
C11—C10—H10119.3C48—C53—H53120.2
C10—C11—C12118.8 (3)O45—C54—O44119.5 (3)
C10—C11—C27121.3 (4)O45—C54—C55122.2 (3)
C12—C11—C27120.0 (4)O44—C54—C55118.3 (3)
C11—C12—C13120.2 (4)C60—C55—C56118.6 (3)
C11—C12—H12119.9C60—C55—C54120.5 (3)
C13—C12—H12119.9C56—C55—C54121.0 (3)
C8—C13—C12120.3 (4)O46—C56—C57118.1 (3)
C8—C13—H13119.8O46—C56—C55122.5 (3)
C12—C13—H13119.8C57—C56—C55119.5 (3)
O5—C14—O4119.4 (3)C58—C57—C56121.3 (3)
O5—C14—C15122.7 (3)C58—C57—H57119.3
O4—C14—C15117.9 (3)C56—C57—H57119.3
C20—C15—C16118.9 (3)C57—C58—C59119.3 (3)
C20—C15—C14120.0 (3)C57—C58—H58120.3
C16—C15—C14121.0 (3)C59—C58—H58120.3
O6—C16—C17118.0 (3)C60—C59—C58120.2 (3)
O6—C16—C15122.3 (3)C60—C59—N43115.0 (3)
C17—C16—C15119.8 (3)C58—C59—N43124.8 (3)
C18—C17—C16120.5 (4)C59—C60—C55121.1 (3)
C18—C17—H17119.7C59—C60—H60119.5
C16—C17—H17119.7C55—C60—H60119.5
C17—C18—C19120.0 (3)C66—C61—C62120.1 (3)
C17—C18—H18120.0C66—C61—N44116.2 (3)
C19—C18—H18120.0C62—C61—N44123.8 (3)
C20—C19—C18119.4 (3)C63—C62—C61118.7 (4)
C20—C19—N3114.6 (3)C63—C62—H62120.6
C18—C19—N3126.0 (3)C61—C62—H62120.6
C19—C20—C15121.3 (3)C64—C63—C62122.4 (4)
C19—C20—H20119.4C64—C63—H63118.8
C15—C20—H20119.4C62—C63—H63118.8
C26—C21—C22119.8 (3)C63—C64—C65117.6 (3)
C26—C21—N4116.1 (3)C63—C64—C68121.0 (4)
C22—C21—N4124.1 (3)C65—C64—C68121.4 (4)
C21—C22—C23119.5 (4)C66—C65—C64121.3 (4)
C21—C22—H22120.3C66—C65—H65119.4
C23—C22—H22120.3C64—C65—H65119.4
C24—C23—C22120.7 (4)C61—C66—C65119.9 (4)
C24—C23—H23119.7C61—C66—H66120.0
C22—C23—H23119.7C65—C66—H66120.0
C25—C24—C23118.7 (3)C51—C67—H671109.5
C25—C24—C28120.7 (3)C51—C67—H672109.5
C23—C24—C28120.6 (4)H671—C67—H672109.5
C26—C25—C24120.9 (4)C51—C67—H673109.5
C26—C25—H25119.5H671—C67—H673109.5
C24—C25—H25119.5H672—C67—H673109.5
C25—C26—C21120.4 (4)C64—C68—H681109.5
C25—C26—H26119.8C64—C68—H682109.5
C21—C26—H26119.8H681—C68—H682109.5
C11—C27—H271109.5C64—C68—H683109.5
C11—C27—H272109.5H681—C68—H683109.5
H271—C27—H272109.5H682—C68—H683109.5
C11—C27—H273109.5C70—C69—Sn2115.6 (2)
H271—C27—H273109.5C70—C69—H691108.4
H272—C27—H273109.5Sn2—C69—H691108.4
C24—C28—H281109.5C70—C69—H692108.4
C24—C28—H282109.5Sn2—C69—H692108.4
H281—C28—H282109.5H691—C69—H692107.4
C24—C28—H283109.5C71—C70—C69112.5 (3)
H281—C28—H283109.5C71—C70—H701109.1
H282—C28—H283109.5C69—C70—H701109.1
C30—C29—Sn1117.0 (3)C71—C70—H702109.1
C30—C29—H291108.1C69—C70—H702109.1
Sn1—C29—H291108.1H701—C70—H702107.8
C30—C29—H292108.1C72—C71—C70112.6 (3)
Sn1—C29—H292108.1C72—C71—H711109.1
H291—C29—H292107.3C70—C71—H711109.1
C29—C30—C31110.6 (4)C72—C71—H712109.1
C29—C30—H301109.5C70—C71—H712109.1
C31—C30—H301109.5H711—C71—H712107.8
C29—C30—H302109.5C71—C72—H721109.5
C31—C30—H302109.5C71—C72—H722109.5
H301—C30—H302108.1H721—C72—H722109.5
C32—C31—C30112.2 (4)C71—C72—H723109.5
C32—C31—H311109.2H721—C72—H723109.5
C30—C31—H311109.2H722—C72—H723109.5
C32—C31—H312109.2C74B—C73—Sn2114.5 (3)
C30—C31—H312109.2C74A—C73—Sn2115.6 (4)
H311—C31—H312107.9C74A—C73—H731108.4
C31—C32—H321109.5Sn2—C73—H731108.4
C31—C32—H322109.5C74A—C73—H732108.4
H321—C32—H322109.5Sn2—C73—H732108.4
C31—C32—H323109.5H731—C73—H732107.4
H321—C32—H323109.5C74B—C73—H733108.6
H322—C32—H323109.5Sn2—C73—H733108.6
C34A—C33—Sn1117.5 (3)C74B—C73—H734108.6
C34B—C33—Sn1117.8 (5)Sn2—C73—H734108.6
C34A—C33—H331107.9H733—C73—H734107.6
Sn1—C33—H331107.9C75A—C74A—C73118.4 (9)
C34A—C33—H332107.9C75A—C74A—H741107.7
Sn1—C33—H332107.9C73—C74A—H741107.7
H331—C33—H332107.2C75A—C74A—H742107.7
C34B—C33—H333107.9C73—C74A—H742107.7
Sn1—C33—H333107.9H741—C74A—H742107.1
C34B—C33—H334107.9C76A—C75A—C74A111.8 (7)
Sn1—C33—H334107.9C76A—C75A—H751109.3
H333—C33—H334107.2C74A—C75A—H751109.3
C33—C34A—C35A114.9 (4)C76A—C75A—H752109.3
C33—C34A—H341108.5C74A—C75A—H752109.3
C35A—C34A—H341108.5H751—C75A—H752107.9
C33—C34A—H342108.5C75A—C76A—H761109.5
C35A—C34A—H342108.5C75A—C76A—H762109.5
H341—C34A—H342107.5H761—C76A—H762109.5
C36A—C35A—C34A112.4 (5)C75A—C76A—H763109.5
C36A—C35A—H351109.1H761—C76A—H763109.5
C34A—C35A—H351109.1H762—C76A—H763109.5
C36A—C35A—H352109.1C73—C74B—C75B108.2 (5)
C34A—C35A—H352109.1C73—C74B—H743110.1
H351—C35A—H352107.8C75B—C74B—H743110.1
C35A—C36A—H361109.5C73—C74B—H744110.1
C35A—C36A—H362109.5C75B—C74B—H744110.1
H361—C36A—H362109.5H743—C74B—H744108.4
C35A—C36A—H363109.5C76B—C75B—C74B110.5 (6)
H361—C36A—H363109.5C76B—C75B—H753109.5
H362—C36A—H363109.5C74B—C75B—H753109.5
C33—C34B—C35B116.3 (14)C76B—C75B—H754109.5
C33—C34B—H343108.2C74B—C75B—H754109.5
C35B—C34B—H343108.2H753—C75B—H754108.1
C33—C34B—H344108.2C75B—C76B—H764109.5
C35B—C34B—H344108.2C75B—C76B—H765109.5
H343—C34B—H344107.4H764—C76B—H765109.5
C36B—C35B—C34B111.0 (8)C75B—C76B—H766109.5
C36B—C35B—H353109.4H764—C76B—H766109.5
C34B—C35B—H353109.4H765—C76B—H766109.5
C36B—C35B—H354109.4C85—C80—C81120.0 (5)
C34B—C35B—H354109.4C85—C80—H80120.0
H353—C35B—H354108.0C81—C80—H80120.0
C35B—C36B—H364109.5C82—C81—C80120.9 (5)
C35B—C36B—H365109.5C82—C81—H81119.5
H364—C36B—H365109.5C80—C81—H81119.5
C35B—C36B—H366109.5C81—C82—C83118.4 (5)
H364—C36B—H366109.5C81—C82—H82120.8
H365—C36B—H366109.5C83—C82—H82120.8
O41—Sn2—O4482.81 (9)C84—C83—C82120.4 (5)
O41—Sn2—O45136.85 (8)C84—C83—H83119.8
O41—Sn2—C69102.61 (11)C82—C83—H83119.8
O41—Sn2—C73104.03 (11)C85—C84—C83120.7 (5)
O42—Sn2—O44137.00 (8)C85—C84—H84119.6
O42—Sn2—O45168.83 (7)C83—C84—H84119.6
O42—Sn2—C6986.48 (11)C84—C85—C80119.6 (5)
O42—Sn2—C7389.90 (11)C84—C85—H85120.2
O44—Sn2—C69102.97 (12)C80—C85—H85120.2
C6—N1—N2—C8178.5 (3)Sn2—O42—C41—C42179.5 (3)
C19—N3—N4—C21179.4 (3)Sn2—O41—C41—O420.1 (3)
Sn1—O2—C1—O12.7 (3)Sn2—O41—C41—C42179.5 (2)
Sn1—O2—C1—C2176.7 (3)O42—C41—C42—C47179.0 (3)
Sn1—O1—C1—O23.4 (3)O41—C41—C42—C471.6 (4)
Sn1—O1—C1—C2176.0 (2)O42—C41—C42—C431.2 (5)
O2—C1—C2—C7177.5 (3)O41—C41—C42—C43178.2 (3)
O1—C1—C2—C71.8 (4)C47—C42—C43—O43179.8 (3)
O2—C1—C2—C32.1 (5)C41—C42—C43—O430.1 (5)
O1—C1—C2—C3178.5 (3)C47—C42—C43—C440.5 (5)
C7—C2—C3—O3179.8 (3)C41—C42—C43—C44179.4 (3)
C1—C2—C3—O30.2 (5)O43—C43—C44—C45179.6 (3)
C7—C2—C3—C40.2 (5)C42—C43—C44—C451.0 (5)
C1—C2—C3—C4179.8 (3)C43—C44—C45—C460.6 (5)
O3—C3—C4—C5179.3 (3)C44—C45—C46—C470.4 (5)
C2—C3—C4—C50.6 (5)C44—C45—C46—N41179.4 (3)
C3—C4—C5—C60.9 (5)N42—N41—C46—C47174.7 (3)
C4—C5—C6—C70.7 (5)N42—N41—C46—C456.3 (4)
C4—C5—C6—N1179.3 (3)C45—C46—C47—C421.0 (5)
N2—N1—C6—C7177.7 (3)N41—C46—C47—C42179.9 (3)
N2—N1—C6—C52.3 (5)C43—C42—C47—C460.6 (5)
C5—C6—C7—C20.3 (5)C41—C42—C47—C46179.6 (3)
N1—C6—C7—C2179.7 (3)N41—N42—C48—C492.2 (5)
C3—C2—C7—C60.0 (5)N41—N42—C48—C53177.9 (3)
C1—C2—C7—C6179.6 (3)C53—C48—C49—C500.3 (5)
N1—N2—C8—C13179.6 (3)N42—C48—C49—C50179.5 (3)
N1—N2—C8—C90.6 (5)C48—C49—C50—C510.1 (5)
C13—C8—C9—C101.3 (5)C49—C50—C51—C520.6 (5)
N2—C8—C9—C10179.0 (3)C49—C50—C51—C67179.6 (3)
C8—C9—C10—C110.2 (5)C50—C51—C52—C531.0 (5)
C9—C10—C11—C121.4 (5)C67—C51—C52—C53179.2 (3)
C9—C10—C11—C27178.8 (3)C51—C52—C53—C480.8 (5)
C10—C11—C12—C131.2 (5)C49—C48—C53—C520.1 (5)
C27—C11—C12—C13179.0 (3)N42—C48—C53—C52179.9 (3)
C9—C8—C13—C121.5 (5)Sn2—O45—C54—O441.3 (3)
N2—C8—C13—C12178.8 (3)Sn2—O45—C54—C55179.2 (3)
C11—C12—C13—C80.2 (5)Sn2—O44—C54—O451.6 (3)
Sn1—O5—C14—O44.2 (3)Sn2—O44—C54—C55178.8 (2)
Sn1—O5—C14—C15174.9 (3)O45—C54—C55—C60178.9 (3)
Sn1—O4—C14—O55.4 (3)O44—C54—C55—C600.6 (4)
Sn1—O4—C14—C15173.7 (2)O45—C54—C55—C560.7 (5)
O5—C14—C15—C20178.7 (3)O44—C54—C55—C56179.8 (3)
O4—C14—C15—C200.3 (4)C60—C55—C56—O46179.9 (3)
O5—C14—C15—C162.9 (5)C54—C55—C56—O460.3 (5)
O4—C14—C15—C16176.1 (3)C60—C55—C56—C570.4 (4)
C20—C15—C16—O6179.8 (3)C54—C55—C56—C57179.2 (3)
C14—C15—C16—O64.3 (5)O46—C56—C57—C58179.1 (3)
C20—C15—C16—C170.8 (5)C55—C56—C57—C580.4 (5)
C14—C15—C16—C17175.1 (3)C56—C57—C58—C590.9 (5)
O6—C16—C17—C18178.7 (3)C57—C58—C59—C600.5 (5)
C15—C16—C17—C181.9 (5)C57—C58—C59—N43178.4 (3)
C16—C17—C18—C191.2 (5)N44—N43—C59—C60173.1 (3)
C17—C18—C19—C200.6 (5)N44—N43—C59—C588.0 (5)
C17—C18—C19—N3179.1 (3)C58—C59—C60—C550.2 (5)
N4—N3—C19—C20179.5 (3)N43—C59—C60—C55179.3 (3)
N4—N3—C19—C180.9 (5)C56—C55—C60—C590.7 (5)
C18—C19—C20—C151.7 (5)C54—C55—C60—C59178.9 (3)
N3—C19—C20—C15179.6 (3)N43—N44—C61—C66175.9 (3)
C16—C15—C20—C191.0 (5)N43—N44—C61—C624.4 (5)
C14—C15—C20—C19176.9 (3)C66—C61—C62—C631.5 (5)
N3—N4—C21—C26173.7 (3)N44—C61—C62—C63178.2 (3)
N3—N4—C21—C228.1 (5)C61—C62—C63—C641.2 (5)
C26—C21—C22—C230.5 (5)C62—C63—C64—C650.5 (5)
N4—C21—C22—C23178.7 (3)C62—C63—C64—C68179.6 (3)
C21—C22—C23—C240.5 (5)C63—C64—C65—C660.2 (5)
C22—C23—C24—C250.7 (5)C68—C64—C65—C66179.3 (3)
C22—C23—C24—C28179.3 (3)C62—C61—C66—C651.2 (5)
C23—C24—C25—C260.1 (5)N44—C61—C66—C65178.5 (3)
C28—C24—C25—C26179.9 (3)C64—C65—C66—C610.5 (5)
C24—C25—C26—C211.1 (5)Sn2—C69—C70—C7172.9 (4)
C22—C21—C26—C251.3 (5)C69—C70—C71—C72178.3 (3)
N4—C21—C26—C25179.6 (3)Sn2—C73—C74A—C75A55.7 (8)
Sn1—C29—C30—C3175.0 (4)C73—C74A—C75A—C76A65.6 (16)
C29—C30—C31—C32177.9 (4)Sn2—C73—C74B—C75B77.7 (9)
Sn1—C33—C34A—C35A69.3 (7)C73—C74B—C75B—C76B176.5 (9)
C33—C34A—C35A—C36A178.3 (7)C85—C80—C81—C820.3 (7)
Sn1—C33—C34B—C35B49.1 (11)C80—C81—C82—C830.2 (7)
C33—C34B—C35B—C36B80 (2)C81—C82—C83—C841.3 (7)
C46—N41—N42—C48179.5 (3)C82—C83—C84—C852.0 (7)
C59—N43—N44—C61177.5 (3)C83—C84—C85—C801.5 (7)
Sn2—O42—C41—O410.1 (3)C81—C80—C85—C840.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.882.618 (3)145
O6—H6···O50.841.892.631 (3)146
O43—H43···O420.841.902.635 (3)146
O46—H46···O450.841.912.627 (3)142
C28—H281···O4i0.982.563.385 (5)142
C73—H733···O41ii0.992.583.540 (5)162
C30—H301···Cg70.992.833.717 (5)149
C34A—H341···Cg4iii0.992.643.586 (5)160
C34B—H344···Cg4iii0.992.733.662 (13)157
C70—H702···Cg6iii0.992.713.654 (4)159
C74A—H741···Cg9ii0.992.693.643 (7)161
C74B—H743···Cg9ii0.992.833.692 (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)909094.1325 (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)9090103.6085 (5)
V3)2840.09 (4)3591.71 (8)1698.29 (7)3448.21 (6)3630.34 (7)1702.24 (4)
Space groupP1P1P1P21/cP21/cP1
Note: (a) details for compounds (III)–(VI) are taken from Basu Baul et al. (2004).
Table 7. Geometry of the ππ 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).
top
InteractionCgI···CgJCgI···PlaneJCgJ···PlaneIαβγSlippage
Compound (I)
Cg1···Cg1i3.8578 (16)3.5175 (11)3.5174 (11)024.324.31.59
Cg1···Cg3ii3.6778 (16)3.4955 (11)3.4628 (11)7.28 (13)19.718.11.24
Cg5···Cg7ii3.6492 (16)3.4107 (11)3.4990 (11)4.65 (13)16.520.81.04
Compound (II)
Cg1···Cg1iii4.082 (2)3.6860 (14)3.6861 (14)025.425.41.75
Cg1···Cg3iv4.028 (2)3.7388 (14)3.7789 (15)13.98 (17)20.321.81.39
Cg2···Cg6v3.780 (2)3.5022 (15)3.5833 (15)6.24 (18)18.522.11.20
Cg2···Cg8vi3.987 (2)3.7113 (15)3.8503 (15)12.92 (18)15.121.51.04
Cg3···Cg93.680 (2)3.5404 (15)3.505 (2)4.5 (2)17.815.81.12
Cg4···Cg8v3.805 (2)3.4786 (15)3.5700 (15)9.33 (18)20.323.91.32
Cg5···Cg5vii3.9809 (19)3.6944 (14)3.6945 (14)021.921.91.48
Cg5···Cg7i3.955 (2)3.4673 (14)3.5635 (14)4.05 (16)25.728.81.72
Compound (III)
Cg1···Cg3viii3.6225 (14)3.4408 (9)3.4347 (10)1.86 (11)18.518.21.15
Cg2···Cg4viii4.1928 (15)3.6557 (11)3.4482 (11)8.09 (13)34.729.32.39
Compound (IV)
Cg1···Cg3ix3.803 (9)3.4525 (10)3.440 (9)0.5 (7)25.224.81.62
Cg2···Cg4ix3.816 (7)3.4796 (12)3.488 (7)3.6 (6)23.924.21.55
Cg1···Cg2x4.1647 (16)3.4726 (10)3.5033 (12)1.95 (13)32.733.52.25
Compound (V)
Cg1···Cg4vii3.700 (6)3.5000 (8)3.481 (5)4.1 (4)19.819.01.25
Cg2···Cg3vii3.799 (4)3.5128 (8)3.398 (4)4.2 (3)26.622.41.70
Compound (VI)
Cg1···Cg3viii3.6310 (13)3.4220 (10)3.4344 (9)3.21 (11)18.919.51.18
Cg2···Cg4viii4.2534 (14)3.6431 (11)3.3332 (10)7.43 (12)38.431.12.64
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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