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The monomeric organotin(IV) carboxyl­ate [Sn(C4H9)2(C8H8NO2)2] has four molecules in the asymmetric unit. The Sn atom exists in a six-coordinated skew-trapezoidal environment in which the carboxyl­ate group chelates in an anisobidentate manner. In one mol­ecule, one of the butyl groups is disordered; the site occupancy factors are ca 0.7 and 0.3. In all four mol­ecules, the methyl­amino substituents are slightly twisted from the mean planes of the phenyl­ene rings, with dihedral angles of 13.43 (13), 11.34 (12), 14.92 (11) and 11.10 (12)°. The crystal structure is stabilized by N—H...O hydrogen bonds and C—H...π inter­actions. In the crystal packing, the mol­ecules are arranged into chains along the [010] direction. Neighbouring chains are arranged in a T-shaped manner. The crystal structure is an inversion twin.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062411/ng2382sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062411/ng2382Isup2.hkl
Contains datablock I

CCDC reference: 674073

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.029
  • wR factor = 0.060
  • Data-to-parameter ratio = 35.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT112_ALERT_2_A ADDSYM Detects Additional (Pseudo) Symm. Elem... m
Author Response: There is no additional symmetry. The crystal is a twin.

Alert level B PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT115_ALERT_5_B ADDSYM Detects Noncrystallographic Inversion ... 89 PerFi PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.87 Ratio PLAT230_ALERT_2_B Hirshfeld Test Diff for C19A - C20E .. 9.43 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C20A - C20E .. 11.74 su
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.386 From the CIF: _refine_ls_abs_structure_Flack_su 0.009 PLAT033_ALERT_2_C Flack Parameter Value Deviates from zero ....... 0.39 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.96 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.12 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1A - O4A .. 7.29 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1B - O4B .. 7.56 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1C - O2C .. 5.34 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1D - O2D .. 6.44 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19E PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT318_ALERT_2_C Check Hybridisation of N2A in Main Residue . ? PLAT420_ALERT_2_C D-H Without Acceptor N1A - H1AB ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1B - H1NC ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2C - H1NF ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1D - H1NG ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 40
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 35.00 From the CIF: _reflns_number_total 41599 Count of symmetry unique reflns 22249 Completeness (_total/calc) 186.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 19350 Fraction of Friedel pairs measured 0.870 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
1 ALERT level A = In general: serious problem 65 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 77 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The coordination number of organotin(IV) atom vary from four to seven resulting in various kinds of geometric formations (Szorcsik et al., 2004; Yin et al., 2006; Win et al., 2006; Win et al., 2007). In addition, it is well known that organotin(IV) complexes are extensively studied due to their industrial applications as well as biocidal properties (Molloy et al., 1984; Willem et al., 1997; Gielen et al., 2000). Moreover, recent in vitro studies of organotin(IV) complexes on cancer cell lines, bacterial and fungal growths have revealed their inhibitory properties (Teoh et al., 1997; Novelli et al., 1999; Gielen et al., 2000; Tian et al., 2005). Generally the complexes obtained from the reaction of dibutyltin(IV) oxide with carboxylic acid in 1:1 ratio are distannoxane-dimer type whereas in 1:2 ratio will produce monomer type (Yin et al., 2005; Win et al., 2006). In this study, the title compound obtained exhibit a normal monomer type from the 1:2 ratio reaction of dibutyltin(IV) oxide with 4-(methylamino)benzoic acid. In addition, the title complex obtained is similar to that found in the dibutylbis[3-(dimethylamino)benzoato]tin(IV) (Win et al., 2007). The only striking difference is that the methylamine group is substituted at para position in the titled compound whereas the dimethylamine group is substituted at meta position in dibutylbis[3-(dimethylamino)benzoato]tin(IV).

The asymmetric unit of the title complex contains four molecules, A, B, C and D of SnIV complex (Fig. 1). In each molecule, the SnIV is in a six-coordinated skew-trapezoidal environment and coordinates with the two bidentate 4-methylaminobenzoate ligands through O atoms in the equatorial plane (O1, O2, O3 and O4) and the two butyl ligands in the axial positions. There is a disorder of one butyl ligand in molecule A (Fig. 2). In the coordination sphere of SnIV, two Sn—O bond distances lie in the ranges of 2.1320 (16)–2.1467 (16) Å which are shorter than the other two Sn—O distances [in the ranges of 2.3986 (18)–2.5288 (17) Å]. The Sn—O bond distances observed in the title complex are longer than a typical Sn—O bond distance [Yearwood et al., 2002]. The Sn—C distances, in the ranges of 2.115 (2)–2.13192) Å, are similar to the other six similar coordination SnIV complexes (Yearwood et al., 2002). The dihedral angles between the two benzene rings (C1–C6) and (C9–C14) are 13.43 (13) °, 11.34 (12) °, 14.92 (11) ° and 11.10 (12) ° in molecules A, B, C and D, respectively. In each molecule, the methylamino groups are slightly twisted from the mean planes of the attached benzene rings, as indicated by the torsion angles C8–N1–C3–C4 and C16–N2–C11–C12 of 2.0 (4) ° and 14.4 (4) ° in molecule A [3.2 (4) ° and 9.0 (4) ° in molecule B; -8.8 (4) ° and -2.9 (4) ° in molecule C; -7.4 (4) ° and -15.3 (4) ° in molecule D]. Bond lengths and angles observed in the structure are normal.

In the crystal packing (Fig. 3), the molecules are arranged into chains along the [0 1 0] direction. The neighbouring chains are arranged in a T-shape manner (Fig. 3). The crystal is stabilized by N—H···O hydrogen bonds and C—H···π interaction [C8B–H8BC···Cg1 (Table 1); Cg1 is the centroid of C1C–C6C benzene ring].

Related literature top

For related structures of organotin carboxylates, see: Win et al. (2007); Yearwood et al. (2002). For literature on the coordination chemistry and bioactivity of organotin compounds, see, for example: Gielen et al. (2000); Molloy et al. (1984); Novelli et al. (1999); Szorcsik et al. (2004); Yin et al. (2006); Teoh et al. (1997); Tian et al. (2005); Win et al. (2006, 2007); Willem et al. (1997); Yin et al. (2005)..

Experimental top

The title complex was obtained by heating under reflux a 1:2 molar mixture of dibutyltin(IV) oxide (0.75 g, 3 mmol) and 4-(methylamino)benzoic acid (0.91 g, 6 mmol) in toluene-ethanol (4:1, v/v) (50 ml) for 4 h. A clear transparent solution was isolated by filtration and kept in a bottle. After 14 days, colourless crystals (0.54 g, 34% yield) were obtained. M.p. 427–428 K. Calculated for C24H34N2O4Sn: C 54.06, H 6.43, N 5.25 and Sn 22.61%; analysis found C 55.63, H 5.89, N 5.48 and Sn 22.61%.

Refinement top

H atoms attached to N atom except for N2A were located from the difference map and isotropically refined. The remainding H atoms were positioned geometrically and allowed to ride on their parent atoms, with N—H distance of 0.82 Å and C—H = 0.93 Å for aromatic rings and in the ranges 0.96–0.97 Å for CH2 and CH3. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.58 Å from Sn1C and the deepest hole is located at 0.74 Å from Sn1D. The crystal is a twin and the refined BASF value is 0.396(0.009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title complex, showing 50% probability displacement ellipsoids and the atomic numbering. H atoms were omitted for clarify.
[Figure 2] Fig. 2. The molecular structure of the title complex, showing a disorder of one butyl ligand in molecule A.
[Figure 3] Fig. 3. The crystal packing of the title complex, viewed along the c axis.
Dibutylbis[4-(methylamino)benzoato-κ2O,O']tin(IV) top
Crystal data top
[Sn(C4H9)2(C8H8NO2)2]F(000) = 2192
Mr = 533.22Dx = 1.456 Mg m3
Monoclinic, P21Melting point = 427–428 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 15.4440 (3) ÅCell parameters from 41599 reflections
b = 11.7770 (2) Åθ = 0.8–35.0°
c = 27.2069 (5) ŵ = 1.08 mm1
β = 100.482 (1)°T = 100 K
V = 4865.92 (15) Å3Block, colourless
Z = 80.57 × 0.50 × 0.35 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
41599 independent reflections
Radiation source: medium-focus sealed tube37515 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 8.33 pixels mm-1θmax = 35.0°, θmin = 0.8°
ϕ and ω scansh = 2424
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1919
Tmin = 0.577, Tmax = 0.701l = 4343
106321 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.0187P)2 + 1.5089P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.005
41599 reflectionsΔρmax = 0.55 e Å3
1187 parametersΔρmin = 0.78 e Å3
1 restraintAbsolute structure: Flack (1983), 19384 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.386 (9)
Crystal data top
[Sn(C4H9)2(C8H8NO2)2]V = 4865.92 (15) Å3
Mr = 533.22Z = 8
Monoclinic, P21Mo Kα radiation
a = 15.4440 (3) ŵ = 1.08 mm1
b = 11.7770 (2) ÅT = 100 K
c = 27.2069 (5) Å0.57 × 0.50 × 0.35 mm
β = 100.482 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
41599 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
37515 reflections with I > 2σ(I)
Tmin = 0.577, Tmax = 0.701Rint = 0.031
106321 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060Δρmax = 0.55 e Å3
S = 1.04Δρmin = 0.78 e Å3
41599 reflectionsAbsolute structure: Flack (1983), 19384 Friedel pairs
1187 parametersAbsolute structure parameter: 0.386 (9)
1 restraint
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn1A0.732628 (10)0.544969 (10)0.057900 (5)0.01736 (3)
N1A0.61588 (16)0.1306 (2)0.19094 (9)0.0326 (5)
H1AB0.57110.08590.19460.039*
N2A1.09439 (16)1.0706 (2)0.05754 (9)0.0293 (5)
H2AB1.10271.08760.02800.035*
O1A0.64204 (13)0.38967 (17)0.01865 (7)0.0251 (4)
O2A0.74456 (11)0.47719 (15)0.01322 (6)0.0215 (3)
O3A0.83615 (11)0.64668 (15)0.03912 (6)0.0212 (3)
O4A0.81181 (11)0.71292 (14)0.11119 (6)0.0201 (3)
C1A0.59769 (18)0.2520 (3)0.06929 (10)0.0303 (6)
H1AA0.56220.24430.04530.036*
C2A0.58154 (19)0.1864 (3)0.11199 (11)0.0344 (6)
H2AA0.53500.13520.11640.041*
C3A0.63355 (17)0.1954 (2)0.14870 (9)0.0257 (5)
C4A0.70370 (16)0.2726 (2)0.14095 (9)0.0227 (4)
H4AA0.74000.27920.16460.027*
C5A0.71934 (16)0.3392 (2)0.09807 (8)0.0210 (4)
H5AA0.76560.39100.09360.025*
C6A0.66712 (16)0.3297 (2)0.06191 (8)0.0205 (4)
C7A0.68368 (16)0.4004 (2)0.01667 (9)0.0207 (4)
C8A0.6677 (2)0.1329 (3)0.22946 (11)0.0370 (7)
H8AA0.64340.08100.25550.055*
H8AB0.72710.11090.21580.055*
H8AC0.66750.20820.24290.055*
C9A0.94627 (17)0.8284 (2)0.02603 (9)0.0203 (4)
H9AA0.92770.78040.00100.024*
C10A1.00510 (19)0.9144 (3)0.02192 (10)0.0243 (5)
H10A1.02470.92490.00810.029*
C11A1.03589 (17)0.9862 (2)0.06248 (10)0.0218 (5)
C12A1.00413 (16)0.9706 (2)0.10701 (9)0.0197 (4)
H12A1.02401.01710.13440.024*
C13A0.94305 (16)0.8858 (2)0.11050 (9)0.0199 (5)
H13A0.92100.87770.13990.024*
C14A0.91424 (15)0.8127 (2)0.07056 (8)0.0163 (4)
C15A0.85121 (14)0.7213 (2)0.07503 (8)0.0165 (4)
C16A1.14278 (17)1.1324 (2)0.09923 (11)0.0331 (6)
H16A1.18441.18170.08780.050*
H16B1.17351.07990.12330.050*
H16C1.10271.17670.11450.050*
C17A0.62339 (17)0.6552 (2)0.03600 (10)0.0242 (5)
H17A0.60200.68050.06510.029*0.663 (4)
H17B0.57680.61450.01510.029*0.663 (4)
H17I0.63540.72380.05510.029*0.337 (4)
H17J0.57350.62010.04640.029*0.337 (4)
C18A0.6501 (2)0.7609 (3)0.00678 (14)0.0213 (8)0.663 (4)
H18A0.69660.80250.02810.026*0.663 (4)
H18B0.67260.73520.02230.026*0.663 (4)
C19A0.5725 (3)0.8386 (4)0.00959 (14)0.0237 (8)0.663 (4)
H19A0.54780.85980.01940.028*0.663 (4)
H19B0.52750.79760.03230.028*0.663 (4)
C20A0.5961 (3)0.9464 (4)0.03543 (18)0.0348 (10)0.663 (4)
H20A0.54460.99280.04430.052*0.663 (4)
H20B0.61820.92630.06500.052*0.663 (4)
H20C0.64040.98770.01310.052*0.663 (4)
C18E0.5968 (4)0.6871 (6)0.0154 (2)0.0244 (13)0.337 (4)
H18I0.53670.71490.02080.029*0.337 (4)
H18J0.59820.62080.03640.029*0.337 (4)
C19E0.6567 (5)0.7789 (6)0.0306 (2)0.0278 (14)0.337 (4)
H19I0.71760.75570.02040.033*0.337 (4)
H19J0.64510.78620.06670.033*0.337 (4)
C20E0.6436 (9)0.8930 (8)0.0076 (4)0.063 (3)0.337 (4)
H20M0.68160.94810.01880.095*0.337 (4)
H20N0.65750.88720.02820.095*0.337 (4)
H20O0.58340.91640.01760.095*0.337 (4)
C21A0.80764 (17)0.4290 (2)0.10772 (8)0.0240 (4)
H21A0.85270.47030.13020.029*
H21B0.76960.39260.12770.029*
C22A0.85144 (17)0.3379 (2)0.08068 (9)0.0264 (5)
H22A0.87540.37330.05390.032*
H22B0.80710.28370.06570.032*
C23A0.92530 (18)0.2743 (2)0.11496 (11)0.0378 (6)
H23A0.95520.22570.09460.045*
H23B0.96780.32910.13140.045*
C24A0.8941 (2)0.2024 (3)0.15450 (10)0.0459 (8)
H24A0.94410.17590.17800.069*
H24B0.86150.13850.13890.069*
H24C0.85700.24720.17170.069*
Sn1B0.746804 (9)0.524665 (10)0.546591 (5)0.01482 (3)
N1B0.60700 (17)0.1085 (2)0.29977 (9)0.0271 (5)
H1NC0.5652 (19)0.062 (3)0.2985 (11)0.029 (8)*
N2B1.07919 (15)1.0864 (2)0.56370 (8)0.0217 (4)
H1ND1.0979 (17)1.099 (2)0.5372 (10)0.019 (7)*
O1B0.65559 (12)0.36903 (17)0.50943 (7)0.0205 (3)
O2B0.74945 (11)0.46310 (15)0.47291 (6)0.0187 (3)
O3B0.84344 (11)0.63817 (15)0.52590 (6)0.0162 (3)
O4B0.82446 (11)0.68014 (14)0.60184 (6)0.0164 (3)
C1B0.60340 (15)0.2303 (2)0.42298 (9)0.0195 (4)
H1BA0.57290.22080.44920.023*
C2B0.58297 (17)0.1630 (2)0.38097 (9)0.0216 (5)
H2BA0.53890.10850.37910.026*
C3B0.62832 (17)0.1762 (2)0.34081 (9)0.0203 (4)
C4B0.69498 (16)0.2586 (2)0.34474 (9)0.0213 (4)
H4BA0.72570.26860.31870.026*
C5B0.71514 (17)0.3253 (2)0.38746 (9)0.0202 (4)
H5BA0.75980.37900.38980.024*
C6B0.66974 (16)0.3128 (2)0.42658 (9)0.0175 (4)
C7B0.69170 (15)0.3837 (2)0.47170 (8)0.0164 (4)
C8B0.65333 (19)0.1111 (3)0.25801 (10)0.0311 (6)
H8BA0.62970.05400.23420.047*
H8BB0.71480.09670.26980.047*
H8BC0.64620.18450.24240.047*
C9B0.95150 (17)0.8320 (2)0.52154 (9)0.0171 (4)
H9BA0.93770.78790.49280.021*
C10B1.00553 (17)0.9246 (2)0.52179 (9)0.0183 (4)
H10B1.02810.94210.49330.022*
C11B1.02739 (15)0.9938 (2)0.56474 (8)0.0149 (4)
C12B0.99214 (16)0.9656 (2)0.60724 (9)0.0174 (4)
H12B1.00531.01020.63580.021*
C13B0.93774 (16)0.8717 (2)0.60676 (8)0.0165 (4)
H13B0.91490.85400.63520.020*
C14B0.91669 (15)0.8030 (2)0.56432 (8)0.0146 (4)
C15B0.85989 (14)0.7039 (2)0.56509 (8)0.0138 (4)
C16B1.11244 (16)1.1539 (2)0.60725 (9)0.0255 (5)
H16D1.15021.21240.59850.038*
H16E1.14521.10630.63270.038*
H16F1.06411.18790.61960.038*
C17B0.63445 (15)0.6327 (2)0.53074 (8)0.0162 (4)
H17C0.58830.59370.50800.019*
H17D0.61290.64680.56150.019*
C18B0.65272 (16)0.7465 (2)0.50767 (9)0.0174 (4)
H18C0.69990.78500.52990.021*
H18D0.67230.73290.47630.021*
C19B0.57196 (16)0.8227 (2)0.49833 (9)0.0188 (4)
H19C0.55360.83870.52990.023*
H19D0.52410.78330.47710.023*
C20B0.59014 (18)0.9349 (2)0.47347 (10)0.0235 (5)
H20D0.53900.98260.47010.035*
H20E0.60370.91980.44100.035*
H20F0.63910.97260.49370.035*
C21B0.83380 (15)0.4081 (2)0.58966 (9)0.0192 (4)
H21C0.87530.38240.56920.023*
H21H0.86730.44940.61770.023*
C22B0.79490 (14)0.30345 (17)0.61032 (8)0.0189 (4)
H22C0.75950.26200.58300.023*
H22D0.75670.32700.63300.023*
C23B0.86670 (15)0.2251 (2)0.63796 (8)0.0222 (4)
H23C0.90350.19950.61480.027*
H23D0.90360.26780.66430.027*
C24B0.82977 (18)0.1219 (2)0.66084 (9)0.0286 (5)
H24D0.87680.08200.68170.043*
H24E0.80160.07250.63470.043*
H24F0.78760.14630.68060.043*
Sn1C0.748868 (9)0.726987 (11)0.203718 (5)0.01618 (3)
N1C0.42110 (15)0.1625 (2)0.19635 (8)0.0220 (4)
H1NE0.399 (2)0.166 (3)0.2201 (11)0.037 (9)*
N2C0.88531 (16)1.1341 (2)0.45384 (8)0.0268 (5)
H1NF0.912 (2)1.187 (3)0.4497 (12)0.037 (9)*
O1C0.65017 (11)0.61520 (14)0.22304 (6)0.0178 (3)
O2C0.66822 (11)0.56898 (14)0.14741 (6)0.0178 (3)
O3C0.83795 (12)0.88120 (16)0.24196 (6)0.0207 (3)
O4C0.74354 (11)0.78666 (15)0.27766 (6)0.0214 (3)
C1C0.54797 (16)0.4209 (2)0.23189 (8)0.0178 (4)
H1CA0.56330.46690.25990.021*
C2C0.49653 (17)0.3268 (2)0.23438 (9)0.0188 (4)
H2CA0.47820.30950.26420.023*
C3C0.47103 (15)0.2559 (2)0.19256 (9)0.0175 (4)
C4C0.50187 (17)0.2833 (2)0.14830 (8)0.0190 (4)
H4CA0.48660.23750.12020.023*
C5C0.55423 (16)0.3769 (2)0.14622 (8)0.0166 (4)
H5CA0.57450.39300.11680.020*
C6C0.57769 (14)0.44852 (19)0.18754 (8)0.0145 (4)
C7C0.63436 (13)0.54798 (19)0.18478 (7)0.0146 (4)
C8C0.38471 (18)0.0912 (3)0.15440 (10)0.0310 (6)
H8CA0.34550.03670.16470.046*
H8CB0.43160.05240.14260.046*
H8CC0.35300.13740.12800.046*
C9C0.89113 (15)1.0156 (2)0.32983 (8)0.0198 (4)
H9CA0.92231.02540.30390.024*
C10C0.91152 (17)1.0807 (2)0.37248 (9)0.0229 (5)
H10C0.95681.13380.37520.027*
C11C0.86433 (16)1.0677 (2)0.41202 (8)0.0198 (4)
C12C0.79663 (16)0.9871 (2)0.40725 (8)0.0203 (4)
H12C0.76500.97700.43290.024*
C13C0.77690 (15)0.92229 (19)0.36388 (8)0.0177 (4)
H13C0.73140.86960.36070.021*
C14C0.82366 (15)0.93458 (19)0.32534 (8)0.0172 (4)
C15C0.80229 (15)0.86609 (19)0.27941 (8)0.0179 (4)
C16C0.83850 (19)1.1312 (3)0.49476 (9)0.0290 (5)
H16G0.86321.18630.51940.043*
H16H0.84341.05690.50950.043*
H16I0.77761.14850.48280.043*
C17C0.66119 (16)0.8437 (2)0.16031 (9)0.0224 (4)
H17E0.62730.80190.13260.027*
H17H0.62010.86990.18090.027*
C18C0.69914 (16)0.94783 (19)0.13884 (9)0.0238 (4)
H18E0.73540.98970.16570.029*
H18F0.73640.92380.11570.029*
C19C0.62719 (17)1.0251 (2)0.11196 (9)0.0275 (5)
H19E0.59161.05130.13560.033*
H19F0.58930.98170.08630.033*
C20C0.6624 (2)1.1279 (2)0.08780 (11)0.0391 (6)
H20G0.61411.17070.06970.059*
H20H0.69961.10280.06520.059*
H20I0.69591.17480.11330.059*
C21C0.85920 (15)0.6175 (2)0.22200 (8)0.0183 (4)
H21D0.88250.60200.19190.022*
H21E0.90470.65620.24530.022*
C22C0.83832 (16)0.5040 (2)0.24524 (9)0.0194 (4)
H22E0.81720.51890.27610.023*
H22F0.79160.46600.22250.023*
C23C0.91833 (16)0.4259 (2)0.25620 (9)0.0217 (5)
H23G0.93700.40690.22500.026*
H23H0.96630.46590.27700.026*
C24C0.89963 (18)0.3166 (2)0.28241 (10)0.0253 (5)
H24G0.95130.26970.28770.038*
H24H0.85210.27670.26200.038*
H24I0.88370.33470.31400.038*
Sn1D0.766802 (9)0.699798 (10)0.695916 (5)0.01476 (3)
N1D0.89640 (18)1.1199 (2)0.94227 (9)0.0292 (5)
H1NG0.921 (2)1.176 (3)0.9394 (12)0.036 (9)*
N2D0.40765 (14)0.16751 (19)0.68114 (8)0.0216 (4)
H1NH0.3815 (17)0.174 (2)0.7057 (9)0.017 (6)*
O1D0.76113 (11)0.76614 (15)0.76796 (6)0.0199 (3)
O2D0.85658 (12)0.85973 (17)0.73252 (6)0.0200 (3)
O3D0.69154 (10)0.53911 (14)0.64329 (6)0.0169 (3)
O4D0.66745 (11)0.59176 (15)0.71712 (6)0.0179 (3)
C1D0.79077 (17)0.9059 (2)0.85288 (9)0.0209 (4)
H1DA0.74630.85170.85000.025*
C2D0.80864 (17)0.9728 (2)0.89539 (9)0.0226 (5)
H2DA0.77600.96370.92070.027*
C3D0.87579 (17)1.0541 (2)0.90040 (9)0.0226 (5)
C4D0.92355 (17)1.0670 (2)0.86141 (9)0.0213 (4)
H4DA0.96861.12030.86440.026*
C5D0.90425 (16)1.0012 (2)0.81871 (9)0.0195 (4)
H5DA0.93521.01210.79280.023*
C6D0.83835 (15)0.9183 (2)0.81423 (8)0.0158 (4)
C7D0.81927 (15)0.8471 (2)0.76918 (8)0.0169 (4)
C8D0.8455 (2)1.1213 (3)0.98171 (10)0.0338 (6)
H8DA0.87001.17591.00660.051*
H8DB0.84691.04730.99670.051*
H8DC0.78571.14140.96810.051*
C9D0.55920 (16)0.3671 (2)0.63677 (8)0.0163 (4)
H9DA0.58130.38230.60780.020*
C10D0.49843 (16)0.2818 (2)0.63668 (8)0.0173 (4)
H10D0.47900.24140.60740.021*
C11D0.46515 (15)0.2546 (2)0.67969 (8)0.0166 (4)
C12D0.49460 (17)0.3191 (2)0.72343 (9)0.0196 (4)
H12D0.47340.30290.75250.024*
C13D0.55475 (16)0.4059 (2)0.72311 (8)0.0176 (4)
H13D0.57320.44790.75200.021*
C14D0.58832 (15)0.4315 (2)0.67989 (8)0.0143 (4)
C15D0.65201 (14)0.5241 (2)0.67907 (8)0.0153 (4)
C16D0.35988 (16)0.1138 (2)0.63622 (10)0.0258 (5)
H16J0.31790.06100.64510.039*
H16K0.40050.07420.61950.039*
H16L0.32960.17070.61430.039*
C17D0.68483 (18)0.8130 (2)0.64780 (9)0.0243 (5)
H17F0.71760.84300.62350.029*
H17G0.63500.77110.62970.029*
C18D0.65087 (14)0.91159 (18)0.67494 (8)0.0184 (4)
H18G0.69810.96580.68470.022*
H18H0.63310.88360.70510.022*
C19D0.57253 (16)0.9719 (2)0.64257 (9)0.0277 (5)
H19G0.52810.91600.62970.033*
H19H0.54681.02440.66330.033*
C20D0.59772 (19)1.0368 (2)0.59901 (9)0.0354 (6)
H20J0.54531.05980.57660.053*
H20K0.63230.98880.58160.053*
H20L0.63141.10270.61130.053*
C21D0.87957 (15)0.5952 (2)0.71526 (9)0.0173 (4)
H21F0.90280.57810.68530.021*
H21G0.92450.63670.73780.021*
C22D0.86077 (16)0.4838 (2)0.74013 (9)0.0199 (4)
H22G0.83560.50070.76950.024*
H22H0.81750.44090.71710.024*
C23D0.94273 (16)0.4110 (2)0.75557 (9)0.0205 (4)
H23E0.96830.39430.72630.025*
H23F0.98590.45320.77890.025*
C24D0.92202 (19)0.3005 (2)0.77969 (10)0.0266 (5)
H24J0.97480.25610.78810.040*
H24K0.87900.25870.75670.040*
H24L0.89910.31660.80950.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn1A0.01956 (6)0.01543 (6)0.01708 (6)0.00260 (5)0.00330 (5)0.00235 (5)
N1A0.0289 (11)0.0323 (12)0.0341 (11)0.0020 (9)0.0013 (9)0.0172 (10)
N2A0.0278 (10)0.0237 (10)0.0408 (12)0.0058 (8)0.0177 (9)0.0011 (9)
O1A0.0294 (9)0.0232 (9)0.0237 (8)0.0080 (8)0.0074 (7)0.0035 (7)
O2A0.0250 (8)0.0198 (7)0.0202 (7)0.0088 (6)0.0055 (6)0.0057 (6)
O3A0.0211 (7)0.0194 (7)0.0237 (7)0.0052 (6)0.0057 (6)0.0061 (6)
O4A0.0203 (7)0.0186 (8)0.0222 (7)0.0044 (6)0.0059 (5)0.0006 (6)
C1A0.0287 (12)0.0328 (14)0.0307 (12)0.0101 (11)0.0084 (9)0.0098 (10)
C2A0.0294 (12)0.0350 (14)0.0386 (13)0.0144 (12)0.0061 (10)0.0136 (12)
C3A0.0259 (10)0.0222 (10)0.0263 (10)0.0036 (9)0.0029 (8)0.0092 (9)
C4A0.0236 (10)0.0214 (10)0.0223 (9)0.0001 (8)0.0021 (8)0.0047 (8)
C5A0.0203 (9)0.0196 (9)0.0216 (9)0.0031 (8)0.0001 (8)0.0034 (8)
C6A0.0229 (10)0.0175 (9)0.0196 (9)0.0029 (8)0.0006 (8)0.0026 (8)
C7A0.0228 (10)0.0174 (9)0.0208 (9)0.0030 (8)0.0014 (8)0.0025 (8)
C8A0.0375 (14)0.0373 (15)0.0332 (13)0.0117 (12)0.0015 (11)0.0200 (11)
C9A0.0215 (10)0.0186 (9)0.0223 (10)0.0008 (8)0.0079 (8)0.0021 (8)
C10A0.0267 (12)0.0239 (11)0.0262 (10)0.0001 (9)0.0152 (9)0.0007 (8)
C11A0.0188 (10)0.0155 (9)0.0335 (11)0.0012 (8)0.0107 (8)0.0015 (8)
C12A0.0189 (10)0.0163 (9)0.0234 (9)0.0035 (8)0.0029 (8)0.0011 (8)
C13A0.0190 (10)0.0223 (11)0.0185 (9)0.0016 (9)0.0037 (7)0.0003 (8)
C14A0.0155 (9)0.0144 (9)0.0191 (9)0.0000 (8)0.0037 (7)0.0002 (8)
C15A0.0165 (8)0.0152 (9)0.0170 (8)0.0009 (8)0.0005 (7)0.0006 (8)
C16A0.0216 (11)0.0234 (11)0.0545 (16)0.0070 (9)0.0079 (11)0.0021 (11)
C17A0.0224 (11)0.0202 (10)0.0277 (11)0.0006 (9)0.0015 (8)0.0002 (9)
C18A0.0189 (14)0.0187 (15)0.0257 (16)0.0017 (12)0.0025 (12)0.0070 (12)
C19A0.0214 (15)0.0255 (17)0.0225 (15)0.0005 (13)0.0007 (12)0.0013 (13)
C20A0.034 (2)0.0236 (17)0.043 (2)0.0023 (16)0.0024 (17)0.0124 (16)
C18E0.025 (3)0.029 (3)0.017 (2)0.005 (2)0.001 (2)0.004 (2)
C19E0.031 (3)0.032 (3)0.021 (3)0.004 (3)0.006 (2)0.000 (2)
C20E0.124 (10)0.034 (4)0.045 (5)0.011 (5)0.051 (6)0.007 (4)
C21A0.0314 (12)0.0193 (10)0.0196 (9)0.0054 (9)0.0001 (8)0.0052 (8)
C22A0.0301 (12)0.0229 (10)0.0280 (11)0.0026 (9)0.0097 (9)0.0026 (9)
C23A0.0272 (12)0.0313 (13)0.0515 (16)0.0096 (10)0.0017 (11)0.0131 (12)
C24A0.066 (2)0.0389 (16)0.0269 (11)0.0265 (15)0.0066 (12)0.0031 (13)
Sn1B0.01493 (6)0.01194 (6)0.01787 (6)0.00171 (5)0.00371 (5)0.00083 (5)
N1B0.0307 (11)0.0225 (10)0.0264 (10)0.0025 (9)0.0007 (9)0.0085 (9)
N2B0.0256 (9)0.0184 (8)0.0234 (8)0.0076 (7)0.0109 (7)0.0009 (7)
O1B0.0208 (8)0.0171 (8)0.0238 (8)0.0029 (6)0.0046 (6)0.0023 (7)
O2B0.0223 (8)0.0139 (6)0.0205 (7)0.0052 (6)0.0055 (6)0.0051 (6)
O3B0.0169 (7)0.0139 (6)0.0187 (7)0.0027 (6)0.0059 (5)0.0030 (5)
O4B0.0163 (7)0.0145 (7)0.0192 (7)0.0008 (6)0.0050 (5)0.0024 (5)
C1B0.0178 (9)0.0159 (9)0.0242 (9)0.0016 (9)0.0026 (7)0.0009 (9)
C2B0.0211 (10)0.0158 (9)0.0263 (10)0.0035 (9)0.0002 (8)0.0016 (9)
C3B0.0208 (10)0.0143 (9)0.0232 (10)0.0022 (8)0.0029 (8)0.0019 (8)
C4B0.0206 (10)0.0204 (10)0.0230 (10)0.0009 (8)0.0037 (8)0.0019 (8)
C5B0.0206 (10)0.0154 (9)0.0245 (10)0.0007 (8)0.0038 (8)0.0007 (8)
C6B0.0169 (9)0.0115 (8)0.0229 (10)0.0002 (7)0.0010 (8)0.0016 (8)
C7B0.0163 (9)0.0128 (8)0.0198 (9)0.0009 (7)0.0028 (7)0.0002 (7)
C8B0.0326 (13)0.0311 (13)0.0265 (11)0.0091 (11)0.0026 (10)0.0104 (11)
C9B0.0204 (10)0.0162 (9)0.0159 (8)0.0015 (8)0.0062 (8)0.0010 (8)
C10B0.0216 (11)0.0161 (9)0.0197 (9)0.0021 (8)0.0103 (8)0.0009 (8)
C11B0.0164 (9)0.0105 (8)0.0183 (8)0.0009 (7)0.0042 (7)0.0006 (7)
C12B0.0194 (10)0.0169 (9)0.0164 (8)0.0040 (8)0.0048 (7)0.0006 (7)
C13B0.0175 (9)0.0166 (9)0.0163 (8)0.0037 (8)0.0051 (7)0.0009 (8)
C14B0.0140 (9)0.0123 (8)0.0181 (9)0.0000 (7)0.0040 (7)0.0010 (7)
C15B0.0112 (7)0.0119 (8)0.0184 (8)0.0022 (7)0.0029 (6)0.0027 (7)
C16B0.0223 (10)0.0234 (10)0.0311 (11)0.0095 (9)0.0058 (9)0.0054 (9)
C17B0.0145 (9)0.0163 (9)0.0177 (9)0.0007 (7)0.0024 (7)0.0015 (7)
C18B0.0171 (9)0.0181 (10)0.0174 (9)0.0006 (8)0.0043 (7)0.0019 (8)
C19B0.0179 (9)0.0187 (9)0.0201 (9)0.0019 (8)0.0038 (7)0.0033 (8)
C20B0.0238 (11)0.0212 (10)0.0261 (10)0.0028 (9)0.0061 (8)0.0046 (9)
C21B0.0171 (9)0.0161 (9)0.0247 (10)0.0005 (8)0.0041 (8)0.0012 (8)
C22B0.0190 (9)0.0153 (8)0.0231 (9)0.0010 (7)0.0060 (7)0.0004 (7)
C23B0.0245 (10)0.0175 (9)0.0247 (9)0.0015 (9)0.0045 (8)0.0022 (8)
C24B0.0372 (13)0.0206 (10)0.0293 (11)0.0019 (9)0.0090 (9)0.0061 (9)
Sn1C0.01712 (6)0.01329 (6)0.01889 (5)0.00262 (5)0.00528 (5)0.00213 (5)
N1C0.0252 (9)0.0181 (8)0.0246 (9)0.0066 (7)0.0094 (7)0.0007 (7)
N2C0.0300 (11)0.0250 (10)0.0227 (9)0.0033 (9)0.0023 (8)0.0075 (8)
O1C0.0193 (7)0.0169 (7)0.0183 (6)0.0036 (6)0.0060 (5)0.0042 (5)
O2C0.0189 (7)0.0173 (7)0.0183 (7)0.0036 (6)0.0064 (5)0.0001 (6)
O3C0.0211 (8)0.0206 (8)0.0209 (8)0.0048 (7)0.0053 (6)0.0034 (7)
O4C0.0219 (8)0.0202 (7)0.0229 (7)0.0083 (6)0.0059 (6)0.0060 (6)
C1C0.0218 (10)0.0144 (9)0.0189 (9)0.0016 (8)0.0079 (8)0.0017 (7)
C2C0.0232 (11)0.0168 (9)0.0190 (9)0.0014 (8)0.0105 (8)0.0007 (7)
C3C0.0143 (9)0.0148 (9)0.0243 (9)0.0005 (7)0.0058 (7)0.0033 (8)
C4C0.0219 (10)0.0177 (9)0.0174 (9)0.0033 (8)0.0035 (7)0.0026 (8)
C5C0.0195 (9)0.0156 (9)0.0150 (8)0.0040 (8)0.0040 (7)0.0022 (7)
C6C0.0131 (8)0.0135 (8)0.0169 (8)0.0001 (7)0.0027 (7)0.0002 (7)
C7C0.0137 (8)0.0125 (9)0.0178 (8)0.0004 (7)0.0034 (6)0.0012 (7)
C8C0.0279 (12)0.0300 (12)0.0334 (12)0.0146 (10)0.0013 (10)0.0034 (10)
C9C0.0186 (9)0.0183 (10)0.0224 (9)0.0046 (8)0.0033 (7)0.0017 (8)
C10C0.0226 (11)0.0199 (10)0.0244 (10)0.0057 (9)0.0003 (8)0.0044 (9)
C11C0.0209 (10)0.0164 (9)0.0199 (9)0.0016 (8)0.0024 (8)0.0033 (8)
C12C0.0228 (10)0.0183 (9)0.0195 (9)0.0014 (8)0.0032 (8)0.0034 (8)
C13C0.0166 (9)0.0133 (8)0.0231 (9)0.0014 (7)0.0036 (7)0.0016 (7)
C14C0.0182 (9)0.0131 (8)0.0194 (9)0.0014 (7)0.0006 (7)0.0016 (7)
C15C0.0190 (9)0.0137 (8)0.0208 (9)0.0016 (8)0.0031 (7)0.0032 (7)
C16C0.0327 (13)0.0298 (12)0.0221 (10)0.0061 (11)0.0012 (9)0.0077 (10)
C17C0.0233 (10)0.0148 (9)0.0281 (11)0.0000 (8)0.0019 (8)0.0002 (8)
C18C0.0275 (11)0.0177 (9)0.0275 (10)0.0006 (8)0.0084 (8)0.0007 (8)
C19C0.0336 (12)0.0222 (10)0.0253 (10)0.0040 (10)0.0016 (9)0.0020 (9)
C20C0.0494 (17)0.0286 (13)0.0408 (14)0.0065 (12)0.0121 (12)0.0118 (11)
C21C0.0189 (10)0.0175 (9)0.0194 (9)0.0005 (8)0.0059 (7)0.0009 (8)
C22C0.0189 (10)0.0194 (10)0.0208 (9)0.0020 (8)0.0056 (8)0.0000 (8)
C23C0.0193 (10)0.0242 (11)0.0218 (9)0.0026 (9)0.0042 (8)0.0016 (8)
C24C0.0260 (12)0.0237 (11)0.0256 (10)0.0014 (9)0.0031 (9)0.0056 (9)
Sn1D0.01570 (6)0.01273 (6)0.01571 (5)0.00063 (5)0.00253 (5)0.00088 (5)
N1D0.0342 (12)0.0244 (10)0.0276 (10)0.0052 (9)0.0020 (9)0.0126 (9)
N2D0.0231 (9)0.0174 (8)0.0272 (9)0.0052 (7)0.0121 (7)0.0018 (7)
O1D0.0227 (8)0.0168 (7)0.0200 (7)0.0043 (6)0.0034 (6)0.0048 (6)
O2D0.0234 (8)0.0183 (8)0.0186 (7)0.0013 (7)0.0047 (6)0.0020 (6)
O3D0.0178 (6)0.0150 (7)0.0184 (6)0.0019 (6)0.0047 (5)0.0000 (5)
O4D0.0179 (7)0.0158 (7)0.0202 (7)0.0022 (6)0.0042 (6)0.0041 (6)
C1D0.0212 (10)0.0202 (10)0.0200 (9)0.0033 (8)0.0004 (7)0.0003 (8)
C2D0.0252 (11)0.0236 (11)0.0192 (9)0.0006 (9)0.0050 (8)0.0037 (8)
C3D0.0244 (10)0.0188 (10)0.0222 (9)0.0028 (9)0.0019 (8)0.0058 (9)
C4D0.0214 (10)0.0157 (9)0.0249 (10)0.0036 (8)0.0003 (8)0.0057 (8)
C5D0.0189 (9)0.0167 (9)0.0224 (9)0.0015 (8)0.0028 (8)0.0019 (8)
C6D0.0161 (9)0.0141 (9)0.0163 (8)0.0007 (7)0.0006 (7)0.0023 (7)
C7D0.0169 (9)0.0146 (9)0.0182 (9)0.0011 (8)0.0004 (7)0.0011 (8)
C8D0.0394 (15)0.0362 (14)0.0236 (11)0.0075 (12)0.0000 (10)0.0118 (11)
C9D0.0181 (9)0.0157 (9)0.0155 (8)0.0000 (8)0.0040 (7)0.0001 (8)
C10D0.0198 (9)0.0157 (9)0.0171 (8)0.0015 (8)0.0047 (7)0.0003 (7)
C11D0.0162 (9)0.0125 (8)0.0214 (9)0.0015 (7)0.0046 (7)0.0001 (7)
C12D0.0241 (11)0.0188 (10)0.0180 (9)0.0010 (9)0.0094 (8)0.0018 (8)
C13D0.0194 (10)0.0167 (9)0.0165 (9)0.0014 (8)0.0031 (7)0.0014 (8)
C14D0.0134 (9)0.0137 (9)0.0157 (8)0.0027 (7)0.0023 (7)0.0015 (7)
C15D0.0139 (8)0.0125 (8)0.0191 (8)0.0016 (8)0.0017 (7)0.0004 (8)
C16D0.0203 (10)0.0207 (10)0.0367 (12)0.0052 (8)0.0062 (9)0.0022 (9)
C17D0.0342 (13)0.0194 (10)0.0174 (9)0.0078 (9)0.0002 (8)0.0017 (8)
C18D0.0178 (9)0.0170 (8)0.0214 (9)0.0039 (7)0.0057 (7)0.0043 (7)
C19D0.0235 (10)0.0272 (11)0.0299 (11)0.0095 (9)0.0021 (8)0.0087 (9)
C20D0.0462 (15)0.0286 (13)0.0277 (11)0.0168 (12)0.0035 (10)0.0031 (11)
C21D0.0164 (9)0.0182 (10)0.0178 (9)0.0002 (8)0.0045 (7)0.0010 (8)
C22D0.0192 (10)0.0192 (10)0.0221 (10)0.0021 (8)0.0055 (8)0.0033 (8)
C23D0.0190 (10)0.0195 (9)0.0229 (9)0.0032 (8)0.0033 (7)0.0008 (8)
C24D0.0297 (12)0.0216 (10)0.0280 (11)0.0019 (9)0.0043 (9)0.0043 (9)
Geometric parameters (Å, º) top
Sn1A—C21A2.115 (2)C23B—C24B1.522 (3)
Sn1A—C17A2.126 (3)C23B—H23C0.9700
Sn1A—O2A2.1320 (16)C23B—H23D0.9700
Sn1A—O3A2.1329 (17)C24B—H24D0.9600
Sn1A—O1A2.4288 (19)C24B—H24E0.9600
N1A—C3A1.366 (3)C24B—H24F0.9600
N1A—C8A1.430 (4)Sn1C—C21C2.123 (2)
N1A—H1AB0.8600Sn1C—C17C2.129 (2)
N2A—C11A1.366 (3)Sn1C—O4C2.1467 (16)
N2A—C16A1.437 (4)Sn1C—O1C2.1505 (16)
N2A—H2AB0.8600Sn1C—O3C2.3986 (18)
O1A—C7A1.256 (3)N1C—C3C1.358 (3)
O2A—C7A1.296 (3)N1C—C8C1.446 (3)
O3A—C15A1.303 (3)N1C—H1NE0.79 (3)
O4A—C15A1.251 (3)N2C—C11C1.370 (3)
C1A—C2A1.379 (4)N2C—C16C1.434 (4)
C1A—C6A1.397 (4)N2C—H1NF0.77 (3)
C1A—H1AA0.9300O1C—C7C1.295 (3)
C2A—C3A1.395 (4)O2C—C7C1.250 (2)
C2A—H2AA0.9300O3C—C15C1.256 (3)
C3A—C4A1.400 (4)O4C—C15C1.298 (3)
C4A—C5A1.391 (3)C1C—C2C1.372 (3)
C4A—H4AA0.9300C1C—C6C1.405 (3)
C5A—C6A1.386 (3)C1C—H1CA0.9300
C5A—H5AA0.9300C2C—C3C1.408 (3)
C6A—C7A1.469 (3)C2C—H2CA0.9300
C8A—H8AA0.9600C3C—C4C1.411 (3)
C8A—H8AB0.9600C4C—C5C1.375 (3)
C8A—H8AC0.9600C4C—H4CA0.9300
C9A—C10A1.378 (4)C5C—C6C1.399 (3)
C9A—C14A1.402 (3)C5C—H5CA0.9300
C9A—H9AA0.9300C6C—C7C1.472 (3)
C10A—C11A1.403 (4)C8C—H8CA0.9600
C10A—H10A0.9300C8C—H8CB0.9600
C11A—C12A1.400 (3)C8C—H8CC0.9600
C12A—C13A1.388 (4)C9C—C10C1.379 (3)
C12A—H12A0.9300C9C—C14C1.401 (3)
C13A—C14A1.394 (3)C9C—H9CA0.9300
C13A—H13A0.9300C10C—C11C1.413 (3)
C14A—C15A1.472 (3)C10C—H10C0.9300
C16A—H16A0.9600C11C—C12C1.401 (3)
C16A—H16B0.9600C12C—C13C1.392 (3)
C16A—H16C0.9600C12C—H12C0.9300
C17A—C18E1.435 (6)C13C—C14C1.385 (3)
C17A—C18A1.572 (5)C13C—H13C0.9300
C17A—H17A0.9601C14C—C15C1.473 (3)
C17A—H17B0.9600C16C—H16G0.9600
C17A—H17I0.9599C16C—H16H0.9600
C17A—H17J0.9599C16C—H16I0.9600
C18A—C19A1.510 (5)C17C—C18C1.521 (3)
C18A—H18A0.9700C17C—H17E0.9700
C18A—H18B0.9700C17C—H17H0.9700
C19A—C20A1.527 (6)C18C—C19C1.517 (3)
C19A—H19A0.9700C18C—H18E0.9700
C19A—H19B0.9700C18C—H18F0.9700
C20A—H20A0.9600C19C—C20C1.524 (4)
C20A—H20B0.9600C19C—H19E0.9700
C20A—H20C0.9600C19C—H19F0.9700
C18E—C19E1.528 (9)C20C—H20G0.9600
C18E—H17B1.2682C20C—H20H0.9600
C18E—H18I0.9700C20C—H20I0.9600
C18E—H18J0.9700C21C—C22C1.537 (3)
C19E—C20E1.512 (11)C21C—H21D0.9700
C19E—H19I0.9700C21C—H21E0.9700
C19E—H19J0.9700C22C—C23C1.526 (4)
C20E—H20M0.9600C22C—H22E0.9700
C20E—H20N0.9600C22C—H22F0.9700
C20E—H20O0.9600C23C—C24C1.524 (4)
C21A—C22A1.526 (4)C23C—H23G0.9700
C21A—H21A0.9700C23C—H23H0.9700
C21A—H21B0.9700C24C—H24G0.9600
C22A—C23A1.532 (4)C24C—H24H0.9600
C22A—H22A0.9700C24C—H24I0.9600
C22A—H22B0.9700Sn1D—C17D2.119 (2)
C23A—C24A1.515 (4)Sn1D—C21D2.120 (2)
C23A—H23A0.9700Sn1D—O1D2.1266 (16)
C23A—H23B0.9700Sn1D—O4D2.1514 (17)
C24A—H24A0.9600Sn1D—O2D2.4412 (19)
C24A—H24B0.9600Sn1D—O3D2.5252 (17)
C24A—H24C0.9600N1D—C3D1.366 (3)
Sn1B—C21B2.119 (2)N1D—C8D1.441 (4)
Sn1B—C17B2.131 (2)N1D—H1NG0.77 (4)
Sn1B—O2B2.1390 (16)N2D—C11D1.362 (3)
Sn1B—O3B2.1534 (16)N2D—C16D1.453 (3)
Sn1B—O1B2.4182 (19)N2D—H1NH0.84 (3)
Sn1B—O4B2.5288 (17)O1D—C7D1.306 (3)
N1B—C3B1.362 (3)O2D—C7D1.248 (3)
N1B—C8B1.449 (4)O3D—C15D1.252 (3)
N1B—H1NC0.84 (3)O4D—C15D1.294 (3)
N2B—C11B1.356 (3)C1D—C2D1.386 (3)
N2B—C16B1.441 (3)C1D—C6D1.396 (3)
N2B—H1ND0.84 (3)C1D—H1DA0.9300
O1B—C7B1.266 (3)C2D—C3D1.400 (4)
O2B—C7B1.288 (3)C2D—H2DA0.9300
O3B—C15B1.305 (3)C3D—C4D1.406 (4)
O4B—C15B1.256 (2)C4D—C5D1.383 (3)
C1B—C2B1.379 (3)C4D—H4DA0.9300
C1B—C6B1.403 (3)C5D—C6D1.400 (3)
C1B—H1BA0.9300C5D—H5DA0.9300
C2B—C3B1.410 (4)C6D—C7D1.470 (3)
C2B—H2BA0.9300C8D—H8DA0.9600
C3B—C4B1.405 (4)C8D—H8DB0.9600
C4B—C5B1.390 (3)C8D—H8DC0.9600
C4B—H4BA0.9300C9D—C10D1.375 (3)
C5B—C6B1.385 (3)C9D—C14D1.400 (3)
C5B—H5BA0.9300C9D—H9DA0.9300
C6B—C7B1.473 (3)C10D—C11D1.398 (3)
C8B—H8BA0.9600C10D—H10D0.9300
C8B—H8BB0.9600C11D—C12D1.415 (3)
C8B—H8BC0.9600C12D—C13D1.382 (4)
C9B—C10B1.372 (3)C12D—H12D0.9300
C9B—C14B1.410 (3)C13D—C14D1.401 (3)
C9B—H9BA0.9300C13D—H13D0.9300
C10B—C11B1.414 (3)C14D—C15D1.472 (3)
C10B—H10B0.9300C16D—H16J0.9600
C11B—C12B1.404 (3)C16D—H16K0.9600
C12B—C13B1.388 (3)C16D—H16L0.9600
C12B—H12B0.9300C17D—C18D1.520 (3)
C13B—C14B1.399 (3)C17D—H17F0.9700
C13B—H13B0.9300C17D—H17G0.9700
C14B—C15B1.462 (3)C18D—C19D1.535 (3)
C16B—H16D0.9600C18D—H18G0.9700
C16B—H16E0.9600C18D—H18H0.9700
C16B—H16F0.9600C19D—C20D1.519 (4)
C17B—C18B1.528 (4)C19D—H19G0.9700
C17B—H17C0.9700C19D—H19H0.9700
C17B—H17D0.9700C20D—H20J0.9600
C18B—C19B1.520 (4)C20D—H20K0.9600
C18B—H18C0.9700C20D—H20L0.9600
C18B—H18D0.9700C21D—C22D1.528 (3)
C19B—C20B1.533 (4)C21D—H21F0.9700
C19B—H19C0.9700C21D—H21G0.9700
C19B—H19D0.9700C22D—C23D1.523 (3)
C20B—H20D0.9600C22D—H22G0.9700
C20B—H20E0.9600C22D—H22H0.9700
C20B—H20F0.9600C23D—C24D1.518 (4)
C21B—C22B1.523 (3)C23D—H23E0.9700
C21B—H21C0.9700C23D—H23F0.9700
C21B—H21H0.9700C24D—H24J0.9600
C22B—C23B1.531 (3)C24D—H24K0.9600
C22B—H22C0.9700C24D—H24L0.9600
C22B—H22D0.9700
C21A—Sn1A—C17A152.63 (10)C23B—C22B—H22C109.3
C21A—Sn1A—O2A102.24 (8)C21B—C22B—H22D109.3
C17A—Sn1A—O2A99.76 (9)C23B—C22B—H22D109.3
C21A—Sn1A—O3A99.74 (9)H22C—C22B—H22D107.9
C17A—Sn1A—O3A100.45 (9)C24B—C23B—C22B112.96 (19)
O2A—Sn1A—O3A78.49 (6)C24B—C23B—H23C109.0
C21A—Sn1A—O1A90.00 (8)C22B—C23B—H23C109.0
C17A—Sn1A—O1A88.41 (9)C24B—C23B—H23D109.0
O2A—Sn1A—O1A57.11 (6)C22B—C23B—H23D109.0
O3A—Sn1A—O1A135.60 (6)H23C—C23B—H23D107.8
C21A—Sn1A—C7A97.02 (8)C23B—C24B—H24D109.5
C17A—Sn1A—C7A94.38 (9)C23B—C24B—H24E109.5
O2A—Sn1A—C7A28.92 (7)H24D—C24B—H24E109.5
O3A—Sn1A—C7A107.41 (7)C23B—C24B—H24F109.5
O1A—Sn1A—C7A28.19 (7)H24D—C24B—H24F109.5
C3A—N1A—C8A123.6 (3)H24E—C24B—H24F109.5
C3A—N1A—H1AB118.2C21C—Sn1C—C17C157.58 (9)
C8A—N1A—H1AB118.2C21C—Sn1C—O4C98.36 (8)
C11A—N2A—C16A123.3 (2)C17C—Sn1C—O4C100.35 (9)
C11A—N2A—H2AB118.4C21C—Sn1C—O1C98.34 (8)
C16A—N2A—H2AB118.4C17C—Sn1C—O1C97.07 (8)
C7A—O1A—Sn1A85.80 (14)O4C—Sn1C—O1C79.72 (6)
C7A—O2A—Sn1A98.38 (14)C21C—Sn1C—O3C89.19 (8)
C15A—O3A—Sn1A103.79 (13)C17C—Sn1C—O3C90.50 (8)
C2A—C1A—C6A120.3 (2)O4C—Sn1C—O3C57.47 (6)
C2A—C1A—H1AA119.9O1C—Sn1C—O3C137.19 (6)
C6A—C1A—H1AA119.9C21C—Sn1C—C15C94.05 (8)
C1A—C2A—C3A121.4 (3)C17C—Sn1C—C15C96.26 (8)
C1A—C2A—H2AA119.3O4C—Sn1C—C15C29.16 (6)
C3A—C2A—H2AA119.3O1C—Sn1C—C15C108.88 (6)
N1A—C3A—C2A120.5 (3)O3C—Sn1C—C15C28.32 (6)
N1A—C3A—C4A121.3 (2)C3C—N1C—C8C123.7 (2)
C2A—C3A—C4A118.2 (2)C3C—N1C—H1NE111 (2)
C5A—C4A—C3A120.3 (2)C8C—N1C—H1NE121 (2)
C5A—C4A—H4AA119.9C11C—N2C—C16C123.7 (2)
C3A—C4A—H4AA119.9C11C—N2C—H1NF113 (2)
C6A—C5A—C4A121.0 (2)C16C—N2C—H1NF120 (2)
C6A—C5A—H5AA119.5C7C—O1C—Sn1C102.48 (12)
C4A—C5A—H5AA119.5C15C—O3C—Sn1C86.73 (13)
C5A—C6A—C1A118.8 (2)C15C—O4C—Sn1C97.16 (13)
C5A—C6A—C7A120.9 (2)C2C—C1C—C6C120.8 (2)
C1A—C6A—C7A120.3 (2)C2C—C1C—H1CA119.6
O1A—C7A—O2A118.7 (2)C6C—C1C—H1CA119.6
O1A—C7A—C6A123.3 (2)C1C—C2C—C3C121.2 (2)
O2A—C7A—C6A118.0 (2)C1C—C2C—H2CA119.4
O1A—C7A—Sn1A66.00 (13)C3C—C2C—H2CA119.4
O2A—C7A—Sn1A52.70 (11)N1C—C3C—C2C119.9 (2)
C6A—C7A—Sn1A170.69 (17)N1C—C3C—C4C122.3 (2)
N1A—C8A—H8AA109.5C2C—C3C—C4C117.8 (2)
N1A—C8A—H8AB109.5C5C—C4C—C3C120.7 (2)
H8AA—C8A—H8AB109.5C5C—C4C—H4CA119.6
N1A—C8A—H8AC109.5C3C—C4C—H4CA119.6
H8AA—C8A—H8AC109.5C4C—C5C—C6C121.2 (2)
H8AB—C8A—H8AC109.5C4C—C5C—H5CA119.4
C10A—C9A—C14A120.5 (2)C6C—C5C—H5CA119.4
C10A—C9A—H9AA119.7C5C—C6C—C1C118.2 (2)
C14A—C9A—H9AA119.7C5C—C6C—C7C120.53 (19)
C9A—C10A—C11A120.9 (2)C1C—C6C—C7C121.2 (2)
C9A—C10A—H10A119.6O2C—C7C—O1C119.2 (2)
C11A—C10A—H10A119.6O2C—C7C—C6C122.65 (19)
N2A—C11A—C12A121.6 (2)O1C—C7C—C6C118.18 (18)
N2A—C11A—C10A119.8 (2)N1C—C8C—H8CA109.5
C12A—C11A—C10A118.6 (2)N1C—C8C—H8CB109.5
C13A—C12A—C11A120.2 (2)H8CA—C8C—H8CB109.5
C13A—C12A—H12A119.9N1C—C8C—H8CC109.5
C11A—C12A—H12A119.9H8CA—C8C—H8CC109.5
C12A—C13A—C14A121.0 (2)H8CB—C8C—H8CC109.5
C12A—C13A—H13A119.5C10C—C9C—C14C120.3 (2)
C14A—C13A—H13A119.5C10C—C9C—H9CA119.8
C13A—C14A—C9A118.7 (2)C14C—C9C—H9CA119.8
C13A—C14A—C15A120.6 (2)C9C—C10C—C11C120.6 (2)
C9A—C14A—C15A120.7 (2)C9C—C10C—H10C119.7
O4A—C15A—O3A119.4 (2)C11C—C10C—H10C119.7
O4A—C15A—C14A123.1 (2)N2C—C11C—C12C121.6 (2)
O3A—C15A—C14A117.52 (19)N2C—C11C—C10C119.6 (2)
N2A—C16A—H16A109.5C12C—C11C—C10C118.8 (2)
N2A—C16A—H16B109.5C13C—C12C—C11C119.7 (2)
H16A—C16A—H16B109.5C13C—C12C—H12C120.2
N2A—C16A—H16C109.5C11C—C12C—H12C120.2
H16A—C16A—H16C109.5C14C—C13C—C12C121.4 (2)
H16B—C16A—H16C109.5C14C—C13C—H13C119.3
C18E—C17A—C18A49.8 (3)C12C—C13C—H13C119.3
C18E—C17A—Sn1A120.3 (3)C13C—C14C—C9C119.1 (2)
C18A—C17A—Sn1A110.95 (19)C13C—C14C—C15C121.2 (2)
C18E—C17A—H17A130.1C9C—C14C—C15C119.7 (2)
C18A—C17A—H17A109.5O3C—C15C—O4C118.6 (2)
Sn1A—C17A—H17A109.4O3C—C15C—C14C123.1 (2)
C18E—C17A—H17B60.1O4C—C15C—C14C118.2 (2)
C18A—C17A—H17B109.4O3C—C15C—Sn1C64.95 (12)
Sn1A—C17A—H17B109.4O4C—C15C—Sn1C53.69 (11)
H17A—C17A—H17B108.1C14C—C15C—Sn1C171.90 (16)
C18E—C17A—H17I107.4N2C—C16C—H16G109.5
C18A—C17A—H17I64.1N2C—C16C—H16H109.5
Sn1A—C17A—H17I107.3H16G—C16C—H16H109.5
H17A—C17A—H17I49.8N2C—C16C—H16I109.5
H17B—C17A—H17I142.2H16G—C16C—H16I109.5
C18E—C17A—H17J107.2H16H—C16C—H16I109.5
C18A—C17A—H17J141.9C18C—C17C—Sn1C118.86 (16)
Sn1A—C17A—H17J107.1C18C—C17C—H17E107.6
H17A—C17A—H17J58.4Sn1C—C17C—H17E107.6
H17B—C17A—H17J53.5C18C—C17C—H17H107.6
H17I—C17A—H17J106.9Sn1C—C17C—H17H107.6
C19A—C18A—C17A111.2 (3)H17E—C17C—H17H107.0
C19A—C18A—H17I101.8C19C—C18C—C17C111.7 (2)
C19A—C18A—H18A109.4C19C—C18C—H18E109.3
C17A—C18A—H18A109.4C17C—C18C—H18E109.3
H17I—C18A—H18A80.2C19C—C18C—H18F109.3
C19A—C18A—H18B109.4C17C—C18C—H18F109.3
C17A—C18A—H18B109.4H18E—C18C—H18F107.9
H17I—C18A—H18B142.1C18C—C19C—C20C113.4 (2)
H18A—C18A—H18B108.0C18C—C19C—H19E108.9
C18A—C19A—C20A113.3 (3)C20C—C19C—H19E108.9
C18A—C19A—H19A108.9C18C—C19C—H19F108.9
C20A—C19A—H19A108.9C20C—C19C—H19F108.9
C18A—C19A—H19B108.9H19E—C19C—H19F107.7
C20A—C19A—H19B108.9C19C—C20C—H20G109.5
H19A—C19A—H19B107.7C19C—C20C—H20H109.5
C17A—C18E—C19E111.6 (4)H20G—C20C—H20H109.5
C19E—C18E—H17B152.2C19C—C20C—H20I109.5
C17A—C18E—H18I109.3H20G—C20C—H20I109.5
C19E—C18E—H18I109.3H20H—C20C—H20I109.5
H17B—C18E—H18I89.2C22C—C21C—Sn1C113.89 (15)
C17A—C18E—H18J109.3C22C—C21C—H21D108.8
C19E—C18E—H18J109.3Sn1C—C21C—H21D108.8
H17B—C18E—H18J83.0C22C—C21C—H21E108.8
H18I—C18E—H18J108.0Sn1C—C21C—H21E108.8
C20E—C19E—C18E112.6 (6)H21D—C21C—H21E107.7
C20E—C19E—H19I109.1C23C—C22C—C21C112.4 (2)
C18E—C19E—H19I109.1C23C—C22C—H22E109.1
C20E—C19E—H19J109.1C21C—C22C—H22E109.1
C18E—C19E—H19J109.1C23C—C22C—H22F109.1
H19I—C19E—H19J107.8C21C—C22C—H22F109.1
C19E—C20E—H20M109.5H22E—C22C—H22F107.8
C19E—C20E—H20N109.5C24C—C23C—C22C112.6 (2)
H20M—C20E—H20N109.5C24C—C23C—H23G109.1
C19E—C20E—H20O109.5C22C—C23C—H23G109.1
H20M—C20E—H20O109.5C24C—C23C—H23H109.1
H20N—C20E—H20O109.5C22C—C23C—H23H109.1
C22A—C21A—Sn1A112.58 (15)H23G—C23C—H23H107.8
C22A—C21A—H21A109.1C23C—C24C—H24G109.5
Sn1A—C21A—H21A109.1C23C—C24C—H24H109.5
C22A—C21A—H21B109.1H24G—C24C—H24H109.5
Sn1A—C21A—H21B109.1C23C—C24C—H24I109.5
H21A—C21A—H21B107.8H24G—C24C—H24I109.5
C21A—C22A—C23A113.4 (2)H24H—C24C—H24I109.5
C21A—C22A—H22A108.9C17D—Sn1D—C21D152.92 (10)
C23A—C22A—H22A108.9C17D—Sn1D—O1D102.60 (8)
C21A—C22A—H22B108.9C21D—Sn1D—O1D98.89 (8)
C23A—C22A—H22B108.9C17D—Sn1D—O4D99.36 (9)
H22A—C22A—H22B107.7C21D—Sn1D—O4D100.57 (8)
C24A—C23A—C22A114.1 (2)O1D—Sn1D—O4D79.58 (6)
C24A—C23A—H23A108.7C17D—Sn1D—O2D89.87 (8)
C22A—C23A—H23A108.7C21D—Sn1D—O2D88.12 (8)
C24A—C23A—H23B108.7O1D—Sn1D—O2D57.05 (6)
C22A—C23A—H23B108.7O4D—Sn1D—O2D136.62 (6)
H23A—C23A—H23B107.6C17D—Sn1D—O3D87.68 (8)
C23A—C24A—H24A109.5C21D—Sn1D—O3D88.73 (8)
C23A—C24A—H24B109.5O1D—Sn1D—O3D134.91 (6)
H24A—C24A—H24B109.5O4D—Sn1D—O3D55.36 (5)
C23A—C24A—H24C109.5O2D—Sn1D—O3D168.02 (5)
H24A—C24A—H24C109.5C17D—Sn1D—C7D96.85 (8)
H24B—C24A—H24C109.5C21D—Sn1D—C7D93.93 (8)
C21B—Sn1B—C17B155.44 (9)O1D—Sn1D—C7D29.10 (7)
C21B—Sn1B—O2B100.39 (8)O4D—Sn1D—C7D108.67 (7)
C17B—Sn1B—O2B99.57 (8)O2D—Sn1D—C7D27.95 (6)
C21B—Sn1B—O3B98.44 (8)O3D—Sn1D—C7D164.00 (6)
C17B—Sn1B—O3B98.86 (8)C3D—N1D—C8D123.5 (3)
O2B—Sn1B—O3B80.39 (6)C3D—N1D—H1NG116 (2)
C21B—Sn1B—O1B90.16 (8)C8D—N1D—H1NG114 (2)
C17B—Sn1B—O1B88.68 (8)C11D—N2D—C16D122.5 (2)
O2B—Sn1B—O1B57.34 (6)C11D—N2D—H1NH111.3 (19)
O3B—Sn1B—O1B137.72 (6)C16D—N2D—H1NH117.5 (18)
C21B—Sn1B—O4B87.47 (8)C7D—O1D—Sn1D98.52 (13)
C17B—Sn1B—O4B88.21 (7)C7D—O2D—Sn1D85.60 (15)
O2B—Sn1B—O4B135.61 (6)C15D—O3D—Sn1D84.50 (14)
O3B—Sn1B—O4B55.22 (6)C15D—O4D—Sn1D100.73 (13)
O1B—Sn1B—O4B167.04 (5)C2D—C1D—C6D121.2 (2)
C21B—Sn1B—C7B95.87 (8)C2D—C1D—H1DA119.4
C17B—Sn1B—C7B94.74 (8)C6D—C1D—H1DA119.4
O2B—Sn1B—C7B28.83 (6)C1D—C2D—C3D120.1 (2)
O3B—Sn1B—C7B109.22 (7)C1D—C2D—H2DA119.9
O1B—Sn1B—C7B28.51 (6)C3D—C2D—H2DA119.9
O4B—Sn1B—C7B164.44 (6)N1D—C3D—C2D121.7 (2)
C3B—N1B—C8B123.4 (3)N1D—C3D—C4D119.6 (2)
C3B—N1B—H1NC119 (2)C2D—C3D—C4D118.8 (2)
C8B—N1B—H1NC118 (2)C5D—C4D—C3D120.7 (2)
C11B—N2B—C16B123.3 (2)C5D—C4D—H4DA119.6
C11B—N2B—H1ND117.0 (19)C3D—C4D—H4DA119.6
C16B—N2B—H1ND119.1 (19)C4D—C5D—C6D120.4 (2)
C7B—O1B—Sn1B85.78 (14)C4D—C5D—H5DA119.8
C7B—O2B—Sn1B97.98 (13)C6D—C5D—H5DA119.8
C15B—O3B—Sn1B101.30 (13)C1D—C6D—C5D118.8 (2)
C15B—O4B—Sn1B85.21 (14)C1D—C6D—C7D121.0 (2)
C2B—C1B—C6B120.7 (2)C5D—C6D—C7D120.2 (2)
C2B—C1B—H1BA119.7O2D—C7D—O1D118.8 (2)
C6B—C1B—H1BA119.7O2D—C7D—C6D123.1 (2)
C1B—C2B—C3B120.5 (2)O1D—C7D—C6D118.0 (2)
C1B—C2B—H2BA119.7O2D—C7D—Sn1D66.45 (13)
C3B—C2B—H2BA119.7O1D—C7D—Sn1D52.38 (11)
N1B—C3B—C4B122.1 (2)C6D—C7D—Sn1D170.42 (17)
N1B—C3B—C2B119.4 (2)N1D—C8D—H8DA109.5
C4B—C3B—C2B118.5 (2)N1D—C8D—H8DB109.5
C5B—C4B—C3B120.2 (2)H8DA—C8D—H8DB109.5
C5B—C4B—H4BA119.9N1D—C8D—H8DC109.5
C3B—C4B—H4BA119.9H8DA—C8D—H8DC109.5
C6B—C5B—C4B121.0 (2)H8DB—C8D—H8DC109.5
C6B—C5B—H5BA119.5C10D—C9D—C14D120.8 (2)
C4B—C5B—H5BA119.5C10D—C9D—H9DA119.6
C5B—C6B—C1B119.0 (2)C14D—C9D—H9DA119.6
C5B—C6B—C7B120.6 (2)C9D—C10D—C11D121.4 (2)
C1B—C6B—C7B120.4 (2)C9D—C10D—H10D119.3
O1B—C7B—O2B118.9 (2)C11D—C10D—H10D119.3
O1B—C7B—C6B122.0 (2)N2D—C11D—C10D122.5 (2)
O2B—C7B—C6B119.1 (2)N2D—C11D—C12D119.4 (2)
O1B—C7B—Sn1B65.72 (13)C10D—C11D—C12D118.0 (2)
O2B—C7B—Sn1B53.19 (11)C13D—C12D—C11D120.3 (2)
C6B—C7B—Sn1B172.28 (17)C13D—C12D—H12D119.8
N1B—C8B—H8BA109.5C11D—C12D—H12D119.8
N1B—C8B—H8BB109.5C12D—C13D—C14D121.1 (2)
H8BA—C8B—H8BB109.5C12D—C13D—H13D119.5
N1B—C8B—H8BC109.5C14D—C13D—H13D119.5
H8BA—C8B—H8BC109.5C9D—C14D—C13D118.4 (2)
H8BB—C8B—H8BC109.5C9D—C14D—C15D120.1 (2)
C10B—C9B—C14B120.7 (2)C13D—C14D—C15D121.5 (2)
C10B—C9B—H9BA119.6O3D—C15D—O4D119.4 (2)
C14B—C9B—H9BA119.6O3D—C15D—C14D122.6 (2)
C9B—C10B—C11B121.0 (2)O4D—C15D—C14D118.07 (19)
C9B—C10B—H10B119.5N2D—C16D—H16J109.5
C11B—C10B—H10B119.5N2D—C16D—H16K109.5
N2B—C11B—C12B121.7 (2)H16J—C16D—H16K109.5
N2B—C11B—C10B120.0 (2)N2D—C16D—H16L109.5
C12B—C11B—C10B118.3 (2)H16J—C16D—H16L109.5
C13B—C12B—C11B120.4 (2)H16K—C16D—H16L109.5
C13B—C12B—H12B119.8C18D—C17D—Sn1D113.62 (15)
C11B—C12B—H12B119.8C18D—C17D—H17F108.8
C12B—C13B—C14B121.2 (2)Sn1D—C17D—H17F108.8
C12B—C13B—H13B119.4C18D—C17D—H17G108.8
C14B—C13B—H13B119.4Sn1D—C17D—H17G108.8
C13B—C14B—C9B118.4 (2)H17F—C17D—H17G107.7
C13B—C14B—C15B120.0 (2)C17D—C18D—C19D112.37 (19)
C9B—C14B—C15B121.7 (2)C17D—C18D—H18G109.1
O4B—C15B—O3B118.0 (2)C19D—C18D—H18G109.1
O4B—C15B—C14B122.6 (2)C17D—C18D—H18H109.1
O3B—C15B—C14B119.34 (18)C19D—C18D—H18H109.1
N2B—C16B—H16D109.5H18G—C18D—H18H107.9
N2B—C16B—H16E109.5C20D—C19D—C18D113.2 (2)
H16D—C16B—H16E109.5C20D—C19D—H19G108.9
N2B—C16B—H16F109.5C18D—C19D—H19G108.9
H16D—C16B—H16F109.5C20D—C19D—H19H108.9
H16E—C16B—H16F109.5C18D—C19D—H19H108.9
C18B—C17B—Sn1B113.72 (15)H19G—C19D—H19H107.8
C18B—C17B—H17C108.8C19D—C20D—H20J109.5
Sn1B—C17B—H17C108.8C19D—C20D—H20K109.5
C18B—C17B—H17D108.8H20J—C20D—H20K109.5
Sn1B—C17B—H17D108.8C19D—C20D—H20L109.5
H17C—C17B—H17D107.7H20J—C20D—H20L109.5
C19B—C18B—C17B112.31 (19)H20K—C20D—H20L109.5
C19B—C18B—H18C109.1C22D—C21D—Sn1D113.27 (15)
C17B—C18B—H18C109.1C22D—C21D—H21F108.9
C19B—C18B—H18D109.1Sn1D—C21D—H21F108.9
C17B—C18B—H18D109.1C22D—C21D—H21G108.9
H18C—C18B—H18D107.9Sn1D—C21D—H21G108.9
C18B—C19B—C20B111.9 (2)H21F—C21D—H21G107.7
C18B—C19B—H19C109.2C23D—C22D—C21D112.9 (2)
C20B—C19B—H19C109.2C23D—C22D—H22G109.0
C18B—C19B—H19D109.2C21D—C22D—H22G109.0
C20B—C19B—H19D109.2C23D—C22D—H22H109.0
H19C—C19B—H19D107.9C21D—C22D—H22H109.0
C19B—C20B—H20D109.5H22G—C22D—H22H107.8
C19B—C20B—H20E109.5C24D—C23D—C22D111.8 (2)
H20D—C20B—H20E109.5C24D—C23D—H23E109.2
C19B—C20B—H20F109.5C22D—C23D—H23E109.2
H20D—C20B—H20F109.5C24D—C23D—H23F109.2
H20E—C20B—H20F109.5C22D—C23D—H23F109.2
C22B—C21B—Sn1B118.39 (15)H23E—C23D—H23F107.9
C22B—C21B—H21C107.7C23D—C24D—H24J109.5
Sn1B—C21B—H21C107.7C23D—C24D—H24K109.5
C22B—C21B—H21H107.7H24J—C24D—H24K109.5
Sn1B—C21B—H21H107.7C23D—C24D—H24L109.5
H21C—C21B—H21H107.1H24J—C24D—H24L109.5
C21B—C22B—C23B111.73 (17)H24K—C24D—H24L109.5
C21B—C22B—H22C109.3
C21A—Sn1A—O1A—C7A104.99 (16)O4B—Sn1B—C21B—C22B129.92 (18)
C17A—Sn1A—O1A—C7A102.34 (16)C7B—Sn1B—C21B—C22B65.32 (18)
O2A—Sn1A—O1A—C7A0.36 (14)Sn1B—C21B—C22B—C23B176.83 (15)
O3A—Sn1A—O1A—C7A1.01 (19)C21B—C22B—C23B—C24B177.7 (2)
C21A—Sn1A—O2A—C7A82.29 (16)C21C—Sn1C—O1C—C7C78.75 (14)
C17A—Sn1A—O2A—C7A81.32 (16)C17C—Sn1C—O1C—C7C84.92 (14)
O3A—Sn1A—O2A—C7A179.89 (16)O4C—Sn1C—O1C—C7C175.79 (14)
O1A—Sn1A—O2A—C7A0.35 (14)O3C—Sn1C—O1C—C7C176.64 (12)
C21A—Sn1A—O3A—C15A84.75 (15)C15C—Sn1C—O1C—C7C175.96 (13)
C17A—Sn1A—O3A—C15A76.66 (16)C21C—Sn1C—O3C—C15C100.08 (15)
O2A—Sn1A—O3A—C15A174.61 (15)C17C—Sn1C—O3C—C15C102.34 (15)
O1A—Sn1A—O3A—C15A175.16 (13)O4C—Sn1C—O3C—C15C0.37 (13)
C7A—Sn1A—O3A—C15A174.66 (14)O1C—Sn1C—O3C—C15C1.35 (18)
C6A—C1A—C2A—C3A0.1 (5)C21C—Sn1C—O4C—C15C83.29 (15)
C8A—N1A—C3A—C2A178.2 (3)C17C—Sn1C—O4C—C15C84.28 (15)
C8A—N1A—C3A—C4A2.0 (4)O1C—Sn1C—O4C—C15C179.68 (15)
C1A—C2A—C3A—N1A179.3 (3)O3C—Sn1C—O4C—C15C0.36 (13)
C1A—C2A—C3A—C4A0.5 (5)C6C—C1C—C2C—C3C0.8 (4)
N1A—C3A—C4A—C5A178.8 (2)C8C—N1C—C3C—C2C173.8 (3)
C2A—C3A—C4A—C5A1.1 (4)C8C—N1C—C3C—C4C8.8 (4)
C3A—C4A—C5A—C6A1.0 (4)C1C—C2C—C3C—N1C179.1 (2)
C4A—C5A—C6A—C1A0.3 (4)C1C—C2C—C3C—C4C1.5 (4)
C4A—C5A—C6A—C7A179.9 (2)N1C—C3C—C4C—C5C178.3 (2)
C2A—C1A—C6A—C5A0.3 (4)C2C—C3C—C4C—C5C0.7 (4)
C2A—C1A—C6A—C7A179.3 (3)C3C—C4C—C5C—C6C0.8 (4)
Sn1A—O1A—C7A—O2A0.6 (2)C4C—C5C—C6C—C1C1.5 (4)
Sn1A—O1A—C7A—C6A179.6 (2)C4C—C5C—C6C—C7C179.6 (2)
Sn1A—O2A—C7A—O1A0.7 (3)C2C—C1C—C6C—C5C0.7 (4)
Sn1A—O2A—C7A—C6A179.52 (19)C2C—C1C—C6C—C7C178.8 (2)
C5A—C6A—C7A—O1A175.1 (2)Sn1C—O1C—C7C—O2C7.4 (2)
C1A—C6A—C7A—O1A5.3 (4)Sn1C—O1C—C7C—C6C171.81 (16)
C5A—C6A—C7A—O2A4.7 (4)C5C—C6C—C7C—O2C4.6 (3)
C1A—C6A—C7A—O2A174.9 (2)C1C—C6C—C7C—O2C173.4 (2)
C21A—Sn1A—C7A—O1A76.72 (16)C5C—C6C—C7C—O1C176.2 (2)
C17A—Sn1A—C7A—O1A78.35 (16)C1C—C6C—C7C—O1C5.8 (3)
O2A—Sn1A—C7A—O1A179.4 (2)C14C—C9C—C10C—C11C0.6 (4)
O3A—Sn1A—C7A—O1A179.26 (14)C16C—N2C—C11C—C12C2.9 (4)
C21A—Sn1A—C7A—O2A102.65 (16)C16C—N2C—C11C—C10C176.8 (2)
C17A—Sn1A—C7A—O2A102.28 (16)C9C—C10C—C11C—N2C179.4 (2)
O3A—Sn1A—C7A—O2A0.11 (16)C9C—C10C—C11C—C12C0.2 (4)
O1A—Sn1A—C7A—O2A179.4 (2)N2C—C11C—C12C—C13C179.3 (2)
C14A—C9A—C10A—C11A1.6 (4)C10C—C11C—C12C—C13C0.4 (3)
C16A—N2A—C11A—C12A14.4 (4)C11C—C12C—C13C—C14C0.9 (3)
C16A—N2A—C11A—C10A166.8 (3)C12C—C13C—C14C—C9C1.2 (3)
C9A—C10A—C11A—N2A179.8 (3)C12C—C13C—C14C—C15C179.7 (2)
C9A—C10A—C11A—C12A1.4 (4)C10C—C9C—C14C—C13C1.1 (4)
N2A—C11A—C12A—C13A178.4 (3)C10C—C9C—C14C—C15C179.6 (2)
C10A—C11A—C12A—C13A0.4 (4)Sn1C—O3C—C15C—O4C0.6 (2)
C11A—C12A—C13A—C14A2.0 (4)Sn1C—O3C—C15C—C14C179.7 (2)
C12A—C13A—C14A—C9A1.8 (4)Sn1C—O4C—C15C—O3C0.7 (2)
C12A—C13A—C14A—C15A178.4 (2)Sn1C—O4C—C15C—C14C179.57 (17)
C10A—C9A—C14A—C13A0.0 (4)C13C—C14C—C15C—O3C173.8 (2)
C10A—C9A—C14A—C15A179.8 (2)C9C—C14C—C15C—O3C4.7 (4)
Sn1A—O3A—C15A—O4A5.5 (2)C13C—C14C—C15C—O4C6.0 (3)
Sn1A—O3A—C15A—C14A174.05 (17)C9C—C14C—C15C—O4C175.5 (2)
C13A—C14A—C15A—O4A9.6 (4)C21C—Sn1C—C15C—O3C80.72 (15)
C9A—C14A—C15A—O4A170.2 (2)C17C—Sn1C—C15C—O3C79.33 (15)
C13A—C14A—C15A—O3A170.9 (2)O4C—Sn1C—C15C—O3C179.4 (2)
C9A—C14A—C15A—O3A9.4 (3)O1C—Sn1C—C15C—O3C179.03 (13)
C21A—Sn1A—C17A—C18E159.5 (3)C21C—Sn1C—C15C—O4C99.91 (15)
O2A—Sn1A—C17A—C18E16.4 (3)C17C—Sn1C—C15C—O4C100.03 (15)
O3A—Sn1A—C17A—C18E63.6 (3)O1C—Sn1C—C15C—O4C0.34 (15)
O1A—Sn1A—C17A—C18E72.6 (3)O3C—Sn1C—C15C—O4C179.4 (2)
C7A—Sn1A—C17A—C18E45.1 (3)C21C—Sn1C—C17C—C18C49.9 (3)
C21A—Sn1A—C17A—C18A145.7 (2)O4C—Sn1C—C17C—C18C96.15 (19)
O2A—Sn1A—C17A—C18A71.2 (2)O1C—Sn1C—C17C—C18C176.93 (18)
O3A—Sn1A—C17A—C18A8.8 (2)O3C—Sn1C—C17C—C18C39.17 (19)
O1A—Sn1A—C17A—C18A127.4 (2)C15C—Sn1C—C17C—C18C66.96 (19)
C7A—Sn1A—C17A—C18A99.8 (2)Sn1C—C17C—C18C—C19C176.28 (17)
C18E—C17A—C18A—C19A66.5 (4)C17C—C18C—C19C—C20C177.3 (2)
Sn1A—C17A—C18A—C19A179.1 (2)C17C—Sn1C—C21C—C22C136.9 (2)
C17A—C18A—C19A—C20A176.5 (3)O4C—Sn1C—C21C—C22C76.80 (17)
C18A—C17A—C18E—C19E14.8 (4)O1C—Sn1C—C21C—C22C3.95 (17)
Sn1A—C17A—C18E—C19E78.0 (5)O3C—Sn1C—C21C—C22C133.74 (16)
C17A—C18E—C19E—C20E71.2 (8)C15C—Sn1C—C21C—C22C105.82 (16)
C17A—Sn1A—C21A—C22A145.9 (2)Sn1C—C21C—C22C—C23C177.99 (16)
O2A—Sn1A—C21A—C22A3.11 (19)C21C—C22C—C23C—C24C176.2 (2)
O3A—Sn1A—C21A—C22A77.10 (18)C17D—Sn1D—O1D—C7D81.36 (16)
O1A—Sn1A—C21A—C22A59.36 (18)C21D—Sn1D—O1D—C7D82.05 (15)
C7A—Sn1A—C21A—C22A31.98 (19)O4D—Sn1D—O1D—C7D178.74 (15)
Sn1A—C21A—C22A—C23A163.91 (18)O2D—Sn1D—O1D—C7D0.15 (13)
C21A—C22A—C23A—C24A66.3 (3)O3D—Sn1D—O1D—C7D179.18 (12)
C21B—Sn1B—O1B—C7B102.08 (15)C17D—Sn1D—O2D—C7D104.99 (15)
C17B—Sn1B—O1B—C7B102.45 (15)C21D—Sn1D—O2D—C7D102.02 (15)
O2B—Sn1B—O1B—C7B0.19 (13)O1D—Sn1D—O2D—C7D0.16 (13)
O3B—Sn1B—O1B—C7B0.70 (19)O4D—Sn1D—O2D—C7D1.42 (18)
O4B—Sn1B—O1B—C7B178.6 (2)O3D—Sn1D—O2D—C7D176.8 (2)
C21B—Sn1B—O2B—C7B83.26 (15)C17D—Sn1D—O3D—C15D104.21 (15)
C17B—Sn1B—O2B—C7B82.38 (15)C21D—Sn1D—O3D—C15D102.63 (14)
O3B—Sn1B—O2B—C7B179.84 (15)O1D—Sn1D—O3D—C15D1.32 (17)
O1B—Sn1B—O2B—C7B0.19 (13)O4D—Sn1D—O3D—C15D1.16 (13)
O4B—Sn1B—O2B—C7B179.67 (12)O2D—Sn1D—O3D—C15D177.4 (3)
C21B—Sn1B—O3B—C15B83.73 (15)C7D—Sn1D—O3D—C15D2.8 (3)
C17B—Sn1B—O3B—C15B78.77 (14)C17D—Sn1D—O4D—C15D81.72 (15)
O2B—Sn1B—O3B—C15B177.07 (14)C21D—Sn1D—O4D—C15D79.87 (15)
O1B—Sn1B—O3B—C15B176.63 (12)O1D—Sn1D—O4D—C15D177.08 (15)
O4B—Sn1B—O3B—C15B2.79 (12)O2D—Sn1D—O4D—C15D178.43 (13)
C7B—Sn1B—O3B—C15B176.98 (13)O3D—Sn1D—O4D—C15D1.14 (12)
C21B—Sn1B—O4B—C15B104.95 (14)C7D—Sn1D—O4D—C15D177.72 (13)
C17B—Sn1B—O4B—C15B99.23 (14)C6D—C1D—C2D—C3D0.5 (4)
O2B—Sn1B—O4B—C15B2.66 (17)C8D—N1D—C3D—C2D7.4 (4)
O3B—Sn1B—O4B—C15B2.86 (12)C8D—N1D—C3D—C4D173.3 (3)
O1B—Sn1B—O4B—C15B175.4 (2)C1D—C2D—C3D—N1D178.6 (3)
C7B—Sn1B—O4B—C15B2.1 (3)C1D—C2D—C3D—C4D0.7 (4)
C6B—C1B—C2B—C3B0.1 (4)N1D—C3D—C4D—C5D179.7 (3)
C8B—N1B—C3B—C4B3.2 (4)C2D—C3D—C4D—C5D0.4 (4)
C8B—N1B—C3B—C2B176.2 (3)C3D—C4D—C5D—C6D1.8 (4)
C1B—C2B—C3B—N1B179.9 (2)C2D—C1D—C6D—C5D0.9 (4)
C1B—C2B—C3B—C4B0.4 (4)C2D—C1D—C6D—C7D180.0 (2)
N1B—C3B—C4B—C5B179.5 (2)C4D—C5D—C6D—C1D2.0 (4)
C2B—C3B—C4B—C5B0.0 (4)C4D—C5D—C6D—C7D178.8 (2)
C3B—C4B—C5B—C6B0.7 (4)Sn1D—O2D—C7D—O1D0.2 (2)
C4B—C5B—C6B—C1B1.0 (4)Sn1D—O2D—C7D—C6D179.5 (2)
C4B—C5B—C6B—C7B179.9 (2)Sn1D—O1D—C7D—O2D0.3 (2)
C2B—C1B—C6B—C5B0.6 (4)Sn1D—O1D—C7D—C6D179.58 (17)
C2B—C1B—C6B—C7B179.5 (2)C1D—C6D—C7D—O2D175.7 (2)
Sn1B—O1B—C7B—O2B0.3 (2)C5D—C6D—C7D—O2D3.5 (4)
Sn1B—O1B—C7B—C6B179.6 (2)C1D—C6D—C7D—O1D5.1 (3)
Sn1B—O2B—C7B—O1B0.3 (2)C5D—C6D—C7D—O1D175.8 (2)
Sn1B—O2B—C7B—C6B179.57 (18)C17D—Sn1D—C7D—O2D76.64 (16)
C5B—C6B—C7B—O1B175.0 (2)C21D—Sn1D—C7D—O2D78.48 (15)
C1B—C6B—C7B—O1B3.9 (4)O1D—Sn1D—C7D—O2D179.7 (2)
C5B—C6B—C7B—O2B4.9 (3)O4D—Sn1D—C7D—O2D178.97 (13)
C1B—C6B—C7B—O2B176.2 (2)O3D—Sn1D—C7D—O2D177.63 (19)
C21B—Sn1B—C7B—O1B79.43 (15)C17D—Sn1D—C7D—O1D103.64 (15)
C17B—Sn1B—C7B—O1B78.40 (15)C21D—Sn1D—C7D—O1D101.24 (15)
O2B—Sn1B—C7B—O1B179.7 (2)O4D—Sn1D—C7D—O1D1.31 (16)
O3B—Sn1B—C7B—O1B179.50 (13)O2D—Sn1D—C7D—O1D179.7 (2)
O4B—Sn1B—C7B—O1B178.81 (19)O3D—Sn1D—C7D—O1D2.1 (3)
C21B—Sn1B—C7B—O2B100.91 (15)C14D—C9D—C10D—C11D1.5 (4)
C17B—Sn1B—C7B—O2B101.27 (15)C16D—N2D—C11D—C10D15.3 (4)
O3B—Sn1B—C7B—O2B0.17 (16)C16D—N2D—C11D—C12D166.3 (2)
O1B—Sn1B—C7B—O2B179.7 (2)C9D—C10D—C11D—N2D177.2 (2)
O4B—Sn1B—C7B—O2B0.9 (3)C9D—C10D—C11D—C12D1.2 (4)
C14B—C9B—C10B—C11B0.4 (4)N2D—C11D—C12D—C13D178.3 (2)
C16B—N2B—C11B—C12B9.0 (4)C10D—C11D—C12D—C13D0.2 (4)
C16B—N2B—C11B—C10B172.9 (2)C11D—C12D—C13D—C14D0.5 (4)
C9B—C10B—C11B—N2B178.4 (2)C10D—C9D—C14D—C13D0.8 (4)
C9B—C10B—C11B—C12B0.2 (4)C10D—C9D—C14D—C15D178.7 (2)
N2B—C11B—C12B—C13B178.6 (2)C12D—C13D—C14D—C9D0.2 (4)
C10B—C11B—C12B—C13B0.4 (4)C12D—C13D—C14D—C15D179.7 (2)
C11B—C12B—C13B—C14B0.0 (4)Sn1D—O3D—C15D—O4D1.8 (2)
C12B—C13B—C14B—C9B0.6 (4)Sn1D—O3D—C15D—C14D177.9 (2)
C12B—C13B—C14B—C15B179.4 (2)Sn1D—O4D—C15D—O3D2.2 (2)
C10B—C9B—C14B—C13B0.8 (4)Sn1D—O4D—C15D—C14D177.53 (17)
C10B—C9B—C14B—C15B179.2 (2)C9D—C14D—C15D—O3D10.2 (3)
Sn1B—O4B—C15B—O3B4.39 (19)C13D—C14D—C15D—O3D170.4 (2)
Sn1B—O4B—C15B—C14B174.2 (2)C9D—C14D—C15D—O4D170.1 (2)
Sn1B—O3B—C15B—O4B5.2 (2)C13D—C14D—C15D—O4D9.3 (3)
Sn1B—O3B—C15B—C14B173.44 (17)C21D—Sn1D—C17D—C18D137.4 (2)
C13B—C14B—C15B—O4B3.9 (3)O1D—Sn1D—C17D—C18D4.26 (19)
C9B—C14B—C15B—O4B176.1 (2)O4D—Sn1D—C17D—C18D85.58 (18)
C13B—C14B—C15B—O3B177.5 (2)O2D—Sn1D—C17D—C18D51.83 (18)
C9B—C14B—C15B—O3B2.5 (3)O3D—Sn1D—C17D—C18D139.90 (18)
C21B—Sn1B—C17B—C18B138.2 (2)C7D—Sn1D—C17D—C18D24.70 (19)
O2B—Sn1B—C17B—C18B77.79 (17)Sn1D—C17D—C18D—C19D163.65 (16)
O3B—Sn1B—C17B—C18B3.87 (17)C17D—C18D—C19D—C20D69.0 (3)
O1B—Sn1B—C17B—C18B134.32 (16)C17D—Sn1D—C21D—C22D140.3 (2)
O4B—Sn1B—C17B—C18B58.25 (16)O1D—Sn1D—C21D—C22D77.46 (17)
C7B—Sn1B—C17B—C18B106.44 (16)O4D—Sn1D—C21D—C22D3.50 (18)
Sn1B—C17B—C18B—C19B178.24 (16)O2D—Sn1D—C21D—C22D133.69 (16)
C17B—C18B—C19B—C20B178.0 (2)O3D—Sn1D—C21D—C22D57.88 (17)
C17B—Sn1B—C21B—C22B49.8 (3)C7D—Sn1D—C21D—C22D106.33 (17)
O2B—Sn1B—C21B—C22B94.09 (18)Sn1D—C21D—C22D—C23D177.97 (16)
O3B—Sn1B—C21B—C22B175.79 (17)C21D—C22D—C23D—C24D179.4 (2)
O1B—Sn1B—C21B—C22B37.34 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AB···O3Ai0.862.313.146 (3)164
N2B—H1ND···O3Bii0.84 (3)2.13 (3)2.967 (3)174 (2)
N1C—H1NE···O4Diii0.78 (3)2.32 (3)3.046 (3)155 (3)
N2D—H1NH···O1Ciii0.84 (3)2.20 (2)2.970 (3)152 (2)
N2D—H1NH···O4Ciii0.84 (3)2.45 (3)3.103 (3)134 (2)
C8B—H8BC···Cg10.962.913.750 (3)147
Symmetry codes: (i) x+2, y+1/2, z; (ii) x+2, y+1/2, z+1; (iii) x+1, y1/2, z+1.

Experimental details

Crystal data
Chemical formula[Sn(C4H9)2(C8H8NO2)2]
Mr533.22
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)15.4440 (3), 11.7770 (2), 27.2069 (5)
β (°) 100.482 (1)
V3)4865.92 (15)
Z8
Radiation typeMo Kα
µ (mm1)1.08
Crystal size (mm)0.57 × 0.50 × 0.35
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.577, 0.701
No. of measured, independent and
observed [I > 2σ(I)] reflections
106321, 41599, 37515
Rint0.031
(sin θ/λ)max1)0.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.060, 1.04
No. of reflections41599
No. of parameters1187
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.55, 0.78
Absolute structureFlack (1983), 19384 Friedel pairs
Absolute structure parameter0.386 (9)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AB···O3Ai0.862.31053.146 (3)164
N2B—H1ND···O3Bii0.84 (3)2.13 (3)2.967 (3)174 (2)
N1C—H1NE···O4Diii0.78 (3)2.32 (3)3.046 (3)155 (3)
N2D—H1NH···O1Ciii0.84 (3)2.20 (2)2.970 (3)152 (2)
N2D—H1NH···O4Ciii0.84 (3)2.45 (3)3.103 (3)134 (2)
C8B—H8BC···Cg10.962.90783.750 (3)147
Symmetry codes: (i) x+2, y+1/2, z; (ii) x+2, y+1/2, z+1; (iii) x+1, y1/2, z+1.
 

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