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The title compound, [Sn2(C14H11N2O4)4(C4H9)4], is a further example from a series of 5-[(E)-aryl­diazen­yl]-2-hydroxy­benzoate complexes with di-n-butyl­tin(IV). The structure consists of centrosymmetric dimers formed by the linking of two monomers via long Sn...O inter­actions of 3.192 (5) Å. Each Sn atom has a skewed trapezoidal bipyramidal inner-sphere coordination geometry with the O atoms from two carboxyl­ate ligands in the equatorial plane and disordered butyl groups occupying axial positions. The singly-bonded carboxyl O atoms from each ligand form coordination Sn—O bonds (ca 2.11 Å) and are cis to one another, while the carbonyl O atoms from the ligands have one lone pair donating into empty orbitals on the Sn atom in a dative fashion, which results in significantly longer Sn—O bonds of ca 2.56 Å. The long Sn...O inter­actions complete a penta­gonal bipyramidal coordination geometry at the Sn atom. Several types of O—H...O hydrogen bonds and C—H...O close contacts are present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020302/lh2373sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020302/lh2373Isup2.hkl
Contains datablock I

CCDC reference: 648081

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.148
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.13 Ratio
Author Response: These result from the model for the disorder of the butyl groups - see exptl_refinement section for details of the disorder treatment.

Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.47 Ratio
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.104 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT213_ALERT_2_C Atom O7 has ADP max/min Ratio ............. 3.20 prola PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O6 PLAT245_ALERT_2_C U(iso) H332 Smaller than U(eq) C35B by ... 0.01 AngSq PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT480_ALERT_4_C Long H...A H-Bond Reported H22 .. O8 .. 2.62 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H271 .. O8 .. 2.62 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H272 .. O4 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H326 .. O3 .. 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H333 .. O7 .. 2.64 Ang.
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The di-n-butyltin(IV) dicarboxylates are widely used as homogeneous catalysts for polyurethane and RTV silicone polymerization and for trans esterification reactions (Evans & Karpel, 1984; Lockhart et al., 1987). We have been studying a series of nBu2Sn(LH)2 complexes (LH = 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoate) (Basu Baul, Dhar & Tiekink, 2001; Basu Baul et al., 2003, 2004, 2005). Some of these complexes exhibit significant biological activity towards Aedes aegypti mosquito larvae (Basu Baul et al., 2003) and in vitro cytotoxicity against human tumor cell lines (Basu Baul et al., 2004). The title compound, (I), whose structure is reported here, is a further member of the nBu2Sn(LH)2 series.

The structure of (I) is related to those several other Sn-complexes built from similar azo-carboxylate ligands (references above). The coordination geometry about the Sn atom is best described as that of a skewed trapezoidal bipyramid (Fig. 1). The carboxylate groups on the two azo-carboxylate ligands act as bidentate chelating ligands, giving rise to an equatorial plane around the Sn atom. The carboxyl O atoms (O1 and O5) from each ligand form coordination bonds and take up a cis arrangement to each other. The carbonyl O atoms (O2 and O6) from the ligands have one lone pair donating into empty orbitals on the Sn atom in a dative fashion, which results in significantly longer Sn—O bonds (Table 1). The O2—Sn1—O6 bond angle between the two carbonyl O atoms is only slightly distorted from linearity by 11.72 (13)°, resulting in one side of the Sn-complex being open for additional coordination. The two butyl groups coordinate to the Sn atom in axial positions, thereby completing the six-coordinate geometry around the Sn atom. The average C—Sn—C angle involving the butyl groups deviates by approximately 47° from linearity. Both of the butyl groups are disordered, with two conformations being present for all atoms in each group. The open side of the Sn1 coordination sphere allows one of the O7 hydroxy atom lone pairs to donate in a weak intermolecular interaction to the Sn1 atom of an adjacent centrosymmetrically related molecule. The internuclear Sn1···O7(1 - x, 1 - y,1 - z) distance is 3.192 (5) Å, which is significantly shorter then the sum of the van der Waals radii for the two atoms. When this weak interaction is considered in the description of the coordination geometry of the Sn atom, a distorted pentagonal bipyramidal geometry is obtained. The centre of inversion between the two molecules involved in this weak interaction means that there are two identical two bridges between the two molecules, so that this Sn-complex exists as a dimer in its crystalline state (Fig. 1).

In (I), the C—N?N—C step present in both azo-carboxylate ligands points in the same direction. The only difference between the two ligands, is that the plane of the methoxyphenyl group of one ligand is tilted 52.7 (3)° out of the plane of the remainder of the carboxylate ligand, whereas the other methoxyphenyl group is oriented more normally and is only tilted by 9.3 (3)° from the remainder of the ligand.

The 2-hydroxybenzoate hydroxy group from both LHH' ligands in compound (I) form classical O—H···O hydrogen bonds with the carboxylate carbonyl oxygen atom on the same ligand (Table 2). The hydroxy oxygen atom involved in the bridging Sn···O interaction can also make an intermolecular O—H···O hydrogen bond with the carboxylate carbonyl oxygen atom in the other ligand across the bridge. The crystal packing in this Sn-complex also affords a geometry that produces several close contacts of the form C—H···O. These interactions have been shown to play an important role in the packing and stability of many organic molecules (Munshi & Guru Row, 2005; Desiraju et al., 1993). For example, the methyl hydrogen (H272) in the more non-planar methoxyphenyl group forms a close contact with the methoxy O atom (O4) in a symmetry related molecule to help stabilize the crystalline state of molecule (I).

Related literature top

For related literature, see: Basu Baul, Dhar & Tiekink (2001); Basu Baul et al. (2001), (2003, 2004, 2005; Desiraju et al. (1993); Evans & Karpel (1984); Lockhart et al. (1987); Munshi & Guru Row (2005).

Experimental top

5-[(E)-2-(2-methoxyphenyl)-1-diazenyl]-2-hydroxybenzoic acid (LHH') was prepared according to the method of Basu Baul, Dhar, Pyke et al. (2001) by a diazo-coupling reaction using o-anisidine and salicylic acid in alkaline medium. The brown coloured precipitate was recrystallized from methanol to give pure LHH' (31.5% yield, m.p. 458–460 K). Analysis calculated for C14H12N2O4Sn: C, 43.01; H, 3.09; N, 7.17%; found: C, 43.09; H, 3.03; N, 7.12%.

The title compound was prepared by refluxing LHH' (0.75 g, 2.75 mmol) and Bu2SnO (0.35 g, 1.40 mmol) in anhydrous toluene (50 ml) in a Dean and Stark apparatus for 3 h. The orange colored solution was filtered, concentrated to one tenth of its initial solvent volume and precipitated with petroleum-ether (333–353 K). The orange coloured precipitate was separated by filtration, washed with hexane (2 x 5 ml) and dried in vacuo. The dried residue was dissolved in hexane and filtered to remove any particles. The filtrate was allowed to evaporate at room temperature, which afforded orange prismatic crystals of (I) (0.75 g, 70% yield, m.p. 352–354 K). Analysis calculated for C36H40N4O8Sn: C, 55.77; H, 5.20; N, 7.23%; found: C, 55.80; H, 5.24; N, 7.20%.

Spectroscopic details for the ligand and for (I) are given in the _exptl_special_details section of the CIF.

Refinement top

All atoms of each butyl group are disordered over two conformations. Refinement of constrained site occupation factors for the two orientations of the C29 to C32 group yielded a value of 0.599 (8) for the major conformation. The two conformations of the C33 to C36 butyl moiety are necessarily equally occupied, because each conformation of this group makes short contacts with itself in a neighbouring molecule related by a twofold axis. Similarity restraints were applied to the chemically equivalent bond lengths and angles involving disordered C atoms, while neighbouring atoms within and between each conformation of the disordered groups were restrained to have similar atomic displacement parameters. The methyl and hydroxy H atoms were constrained to an ideal geometry with C—H and O—H distances of 0.98 and 0.84 Å, respectively, and with Uiso(H) = 1.5Ueq(parent atom), but were allowed to rotate freely about the parent C—C or C—O bonds. All other H atoms were placed geometrically and refined using a riding model with C—H distances of 0.95 Å (phenyl) or 0.99 Å (methylene) and with Uiso(H) = 1.2Ueq(C). One low angle reflection was omitted from the final cycles of refinement because its observed intensity was much lower than the calculated value as a result of being partially obscured by the beam stop.

Structure description top

The di-n-butyltin(IV) dicarboxylates are widely used as homogeneous catalysts for polyurethane and RTV silicone polymerization and for trans esterification reactions (Evans & Karpel, 1984; Lockhart et al., 1987). We have been studying a series of nBu2Sn(LH)2 complexes (LH = 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoate) (Basu Baul, Dhar & Tiekink, 2001; Basu Baul et al., 2003, 2004, 2005). Some of these complexes exhibit significant biological activity towards Aedes aegypti mosquito larvae (Basu Baul et al., 2003) and in vitro cytotoxicity against human tumor cell lines (Basu Baul et al., 2004). The title compound, (I), whose structure is reported here, is a further member of the nBu2Sn(LH)2 series.

The structure of (I) is related to those several other Sn-complexes built from similar azo-carboxylate ligands (references above). The coordination geometry about the Sn atom is best described as that of a skewed trapezoidal bipyramid (Fig. 1). The carboxylate groups on the two azo-carboxylate ligands act as bidentate chelating ligands, giving rise to an equatorial plane around the Sn atom. The carboxyl O atoms (O1 and O5) from each ligand form coordination bonds and take up a cis arrangement to each other. The carbonyl O atoms (O2 and O6) from the ligands have one lone pair donating into empty orbitals on the Sn atom in a dative fashion, which results in significantly longer Sn—O bonds (Table 1). The O2—Sn1—O6 bond angle between the two carbonyl O atoms is only slightly distorted from linearity by 11.72 (13)°, resulting in one side of the Sn-complex being open for additional coordination. The two butyl groups coordinate to the Sn atom in axial positions, thereby completing the six-coordinate geometry around the Sn atom. The average C—Sn—C angle involving the butyl groups deviates by approximately 47° from linearity. Both of the butyl groups are disordered, with two conformations being present for all atoms in each group. The open side of the Sn1 coordination sphere allows one of the O7 hydroxy atom lone pairs to donate in a weak intermolecular interaction to the Sn1 atom of an adjacent centrosymmetrically related molecule. The internuclear Sn1···O7(1 - x, 1 - y,1 - z) distance is 3.192 (5) Å, which is significantly shorter then the sum of the van der Waals radii for the two atoms. When this weak interaction is considered in the description of the coordination geometry of the Sn atom, a distorted pentagonal bipyramidal geometry is obtained. The centre of inversion between the two molecules involved in this weak interaction means that there are two identical two bridges between the two molecules, so that this Sn-complex exists as a dimer in its crystalline state (Fig. 1).

In (I), the C—N?N—C step present in both azo-carboxylate ligands points in the same direction. The only difference between the two ligands, is that the plane of the methoxyphenyl group of one ligand is tilted 52.7 (3)° out of the plane of the remainder of the carboxylate ligand, whereas the other methoxyphenyl group is oriented more normally and is only tilted by 9.3 (3)° from the remainder of the ligand.

The 2-hydroxybenzoate hydroxy group from both LHH' ligands in compound (I) form classical O—H···O hydrogen bonds with the carboxylate carbonyl oxygen atom on the same ligand (Table 2). The hydroxy oxygen atom involved in the bridging Sn···O interaction can also make an intermolecular O—H···O hydrogen bond with the carboxylate carbonyl oxygen atom in the other ligand across the bridge. The crystal packing in this Sn-complex also affords a geometry that produces several close contacts of the form C—H···O. These interactions have been shown to play an important role in the packing and stability of many organic molecules (Munshi & Guru Row, 2005; Desiraju et al., 1993). For example, the methyl hydrogen (H272) in the more non-planar methoxyphenyl group forms a close contact with the methoxy O atom (O4) in a symmetry related molecule to help stabilize the crystalline state of molecule (I).

For related literature, see: Basu Baul, Dhar & Tiekink (2001); Basu Baul et al. (2001), (2003, 2004, 2005; Desiraju et al. (1993); Evans & Karpel (1984); Lockhart et al. (1987); Munshi & Guru Row (2005).

Computing details top

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: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. View of the dimeric molecule of (I) showing the atom-labelling scheme, the long Sn1—O7i interaction (unfilled bonds) and the hydrogen bonds (dashed lines). Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size. Symmetry code: (i) 1 - x, 1 - y, 1 - z. only one component of the disorder is shown
Bis{µ-2-hydroxy-5-[(E)-2-(2-methoxyphenyl)diazenyl]benzoato}bis(di-n- butyl{2-hydroxy-5-[(E)-2-(2-methoxyphenyl)diazenyl]benzoato}tin(IV)) top
Crystal data top
[Sn2(C14H11N2O4)4(C4H9)4]F(000) = 3184
Mr = 1550.66Dx = 1.433 Mg m3
Monoclinic, C2/cMelting point: 353 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 35.6311 (7) ÅCell parameters from 84575 reflections
b = 10.6333 (2) Åθ = 2.0–25.0°
c = 19.5551 (4) ŵ = 0.77 mm1
β = 104.0634 (11)°T = 160 K
V = 7186.9 (2) Å3Prism, orange–red
Z = 40.20 × 0.20 × 0.15 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
6348 independent reflections
Radiation source: Nonius FR590 sealed tube generator4601 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.104
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.0°
φ and ω scans with κ offsetsh = 4242
Absorption correction: multi-scan
(Blessing, 1995)
k = 1212
Tmin = 0.805, Tmax = 0.892l = 2322
70128 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)] = 0.057H-atom parameters constrained
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0562P)2 + 33.1175P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
6347 reflectionsΔρmax = 0.73 e Å3
524 parametersΔρmin = 1.12 e Å3
147 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00054 (9)
Crystal data top
[Sn2(C14H11N2O4)4(C4H9)4]V = 7186.9 (2) Å3
Mr = 1550.66Z = 4
Monoclinic, C2/cMo Kα radiation
a = 35.6311 (7) ŵ = 0.77 mm1
b = 10.6333 (2) ÅT = 160 K
c = 19.5551 (4) Å0.20 × 0.20 × 0.15 mm
β = 104.0634 (11)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
6348 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
4601 reflections with I > 2σ(I)
Tmin = 0.805, Tmax = 0.892Rint = 0.104
70128 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057147 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0562P)2 + 33.1175P]
where P = (Fo2 + 2Fc2)/3
6347 reflectionsΔρmax = 0.73 e Å3
524 parametersΔρmin = 1.12 e Å3
Special details top

Experimental. Solvent used: hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.591 (1) Frames collected: 567 Seconds exposure per frame: 10 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0

Spectroscopic data for the ligand (LHH') IR (KBr, cm-1): 1661 ν(OCO)asym; 1H NMR (DMSO-d6, 300.13 MHz); δH: Ligand skeleton: 4.04 [s, 3H, OCH3], 7.04 [ddd,1H, H-3], 7.11 [dd, 2H, H-3' & H-4'], 7.45 [ddd, 1H, H-5'], 7.68 [dd, 1H, H-6'], 8.14 [dd, 1H, H-4], 8.54 [d, 1H, H-6] p.p.m.. Signals for the phenol and carboxylic acid were exchanged due to presence of water in the solvent; 13C NMR (DMSO-d6, 75.47 MHz); δC: Ligand skeleton: 56.0 [OCH3], 112.7 [C-6'], 112.9 [C-1], 116.6 [C-3], 118.9 [C-6], 120.6 [C-5'], 127.4 [C-4], 128.2 [C-4'], 132.2 [C-3'], 141.8 [C-2'], 145.4 [C-5], 156.5 [C-1'], 164.0 [C-2], 172.3 [CO2] p.p.m..

Spectroscopic data for (I) IR (KBr, cm-1): 1622 ν(OCO)asym; 1H NMR (CDCl3, 300.13 MHz); δH: Ligand skeleton: 4.02 [s, 3H, OCH3], 7.02 [ddd,1H, H-3], 7.10 [dd, 2H, H-3' & H-4'], 7.43 [ddd, 1H, H-5'], 7.69 [dd, 1H, H-6'], 8.13 [dd, 1H, H-4], 8.65 [d, 1H, H-6], 10.98 [s, 1H, OH]; Sn-nBu skeleton: 0.93 [t, 3H, H-4*], 1.45 [m, 2H, H-3*], 1.79 [m, 2H, H-2*], 1.93 [t, 2H, H-1*], p.p.m.. 13C NMR (CDCl3, 75.47 MHz); δC: Ligand skeleton: 56.3 [OCH3], 112.6 [C-6'], 112.8 [C-1], 116.9 [C-3], 118.3 [C-6], 120.7 [C-5'], 128.7 [C-4], 129.2 [C-4'], 132.2 [C-3'], 142.1 [C-2'], 146.1 [C-5], 156.8 [C-1'], 163.7 [C-2], 177.2 [CO2]; Sn-nBu skeleton: 13.5 [C-4*], 26.3 [C-3*], 26.4 [C-2*], 26.5 [C-1*], p.p.m.. 119Sn NMR (CDCl3, 111.92 MHz); δSn: -112.9 p.p.m., 119Sn Mössbauer: δ = 1.52, Δ = 3.69, Γ1 = 0.85, Γ2 = 0.86 mm s-1, C—Sn—C = 152°.

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)
Sn10.440621 (10)0.23007 (4)0.50793 (3)0.0626 (2)
O10.38955 (10)0.1216 (3)0.4884 (2)0.0622 (11)
O20.43609 (12)0.0038 (4)0.5434 (3)0.0775 (13)
O30.42002 (13)0.2343 (4)0.5729 (3)0.0739 (12)
H30.43250.16720.58400.089*
O40.21361 (11)0.1554 (3)0.4502 (2)0.0595 (10)
O50.40166 (9)0.3689 (3)0.4550 (2)0.0546 (10)
O60.45967 (11)0.4485 (4)0.4800 (3)0.0801 (14)
O70.47184 (11)0.6766 (5)0.4421 (4)0.104 (2)
H70.47590.62950.47760.124*
O80.28023 (12)0.9501 (4)0.1671 (2)0.0615 (10)
N10.26745 (13)0.1497 (4)0.4320 (2)0.0515 (11)
N20.25529 (13)0.0380 (4)0.4257 (2)0.0518 (11)
N30.31623 (12)0.6859 (4)0.3049 (2)0.0478 (10)
N40.30688 (12)0.7685 (4)0.2575 (2)0.0462 (10)
C10.40120 (16)0.0127 (6)0.5147 (3)0.0614 (16)
C20.37205 (16)0.0880 (5)0.5096 (3)0.0541 (14)
C30.38338 (17)0.2071 (6)0.5400 (3)0.0589 (15)
C40.35504 (19)0.2998 (5)0.5339 (3)0.0611 (16)
H40.36220.37990.55450.073*
C50.31803 (17)0.2796 (5)0.4998 (3)0.0556 (14)
H50.29950.34510.49670.067*
C60.30644 (16)0.1620 (5)0.4686 (3)0.0499 (13)
C70.33387 (15)0.0672 (5)0.4743 (3)0.0507 (13)
H710.32640.01270.45370.061*
C80.21665 (16)0.0261 (5)0.3836 (3)0.0513 (13)
C90.20017 (18)0.1081 (5)0.3296 (3)0.0598 (15)
H90.21450.17850.32010.072*
C100.16311 (18)0.0885 (7)0.2896 (3)0.0700 (18)
H100.15200.14520.25270.084*
C110.14208 (19)0.0138 (6)0.3031 (4)0.0701 (17)
H110.11650.02710.27570.084*
C120.15840 (17)0.0967 (6)0.3567 (3)0.0608 (15)
H120.14390.16680.36610.073*
C130.19547 (16)0.0780 (5)0.3962 (3)0.0525 (14)
C140.42436 (14)0.4608 (5)0.4515 (3)0.0551 (14)
C150.40969 (14)0.5758 (5)0.4136 (3)0.0476 (13)
C160.43376 (16)0.6769 (6)0.4106 (4)0.0676 (18)
C170.41870 (17)0.7851 (6)0.3733 (4)0.0729 (19)
H170.43510.85500.37210.087*
C180.38074 (16)0.7911 (5)0.3388 (3)0.0573 (15)
H180.37090.86470.31310.069*
C190.35611 (14)0.6903 (5)0.3410 (3)0.0425 (11)
C200.37058 (14)0.5844 (5)0.3788 (3)0.0457 (12)
H200.35370.51620.38130.055*
C210.26767 (15)0.7612 (5)0.2192 (3)0.0457 (12)
C220.24313 (15)0.6617 (5)0.2244 (3)0.0516 (13)
H220.25250.59380.25550.062*
C230.20544 (17)0.6604 (6)0.1849 (3)0.0596 (15)
H230.18860.59300.18910.072*
C240.19255 (19)0.7583 (7)0.1393 (3)0.0735 (19)
H240.16650.75850.11240.088*
C250.21640 (19)0.8555 (6)0.1317 (3)0.0660 (17)
H250.20680.92120.09920.079*
C260.25438 (17)0.8588 (5)0.1710 (3)0.0531 (14)
C270.19379 (19)0.2689 (5)0.4603 (4)0.0676 (17)
H2710.18760.31720.41630.101*
H2720.21040.31930.49760.101*
H2730.16980.24770.47380.101*
C280.2687 (2)1.0449 (6)0.1137 (3)0.081 (2)
H2810.25921.00450.06770.121*
H2820.29091.09830.11250.121*
H2830.24811.09650.12440.121*
C29A0.4745 (7)0.151 (3)0.4441 (9)0.104 (5)0.401 (8)
H2910.50220.15780.46870.125*0.401 (8)
H2920.46820.06050.43670.125*0.401 (8)
C30A0.4676 (6)0.217 (2)0.3722 (10)0.123 (4)0.401 (8)
H3010.47570.30570.38140.147*0.401 (8)
H3020.48540.17860.34640.147*0.401 (8)
C31A0.4272 (6)0.219 (3)0.3217 (12)0.147 (4)0.401 (8)
H3110.40820.26210.34300.176*0.401 (8)
H3120.41790.13230.30810.176*0.401 (8)
C32A0.4340 (9)0.292 (3)0.2580 (13)0.166 (7)0.401 (8)
H3210.44000.38000.27140.249*0.401 (8)
H3220.41070.28830.21930.249*0.401 (8)
H3230.45580.25470.24280.249*0.401 (8)
C29B0.4633 (5)0.1640 (18)0.4227 (7)0.110 (4)0.599 (8)
H2930.48360.22280.41580.132*0.599 (8)
H2940.47550.08090.43530.132*0.599 (8)
C30B0.4318 (5)0.1520 (17)0.3524 (8)0.135 (4)0.599 (8)
H3030.41020.10320.36310.161*0.599 (8)
H3040.42170.23790.33960.161*0.599 (8)
C31B0.4400 (6)0.0947 (19)0.2865 (9)0.171 (5)0.599 (8)
H3130.44900.00670.29480.205*0.599 (8)
H3140.45950.14420.26990.205*0.599 (8)
C32B0.3996 (6)0.101 (2)0.2330 (11)0.188 (6)0.599 (8)
H3240.38160.14880.25390.282*0.599 (8)
H3250.38970.01600.22170.282*0.599 (8)
H3260.40230.14340.18980.282*0.599 (8)
C33A0.4517 (10)0.2667 (15)0.6180 (5)0.096 (4)0.50
H3310.43070.22930.63660.115*0.50
H3320.47630.22550.64210.115*0.50
C34A0.4544 (5)0.4080 (13)0.6348 (6)0.098 (3)0.50
H3410.47520.44740.61650.118*0.50
H3420.42970.45030.61310.118*0.50
C35A0.4636 (6)0.4189 (14)0.7155 (7)0.123 (4)0.50
H3510.44310.37660.73330.147*0.50
H3520.48850.37670.73650.147*0.50
C36A0.4660 (6)0.5578 (15)0.7375 (10)0.134 (5)0.50
H3610.45580.61040.69600.200*0.50
H3620.49310.58030.75810.200*0.50
H3630.45080.57150.77240.200*0.50
C33B0.4473 (9)0.2926 (16)0.6133 (6)0.098 (4)0.50
H3330.47320.33180.62750.118*0.50
H3340.42830.36120.61140.118*0.50
C34B0.4437 (5)0.2066 (16)0.6743 (9)0.109 (4)0.50
H3430.42160.14810.65910.131*0.50
H3440.43970.25690.71460.131*0.50
C35B0.4821 (5)0.1337 (17)0.6950 (10)0.130 (5)0.50
H3530.48770.09470.65260.156*0.50
H3540.50340.19210.71570.156*0.50
C36B0.4791 (6)0.0312 (18)0.7489 (11)0.149 (6)0.50
H3640.47850.07060.79390.223*0.50
H3650.50160.02450.75580.223*0.50
H3660.45540.01770.73140.223*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0315 (2)0.0532 (3)0.0955 (4)0.00124 (17)0.00051 (19)0.0235 (2)
O10.039 (2)0.047 (2)0.097 (3)0.0048 (17)0.009 (2)0.015 (2)
O20.050 (3)0.059 (3)0.118 (4)0.005 (2)0.008 (2)0.022 (3)
O30.064 (3)0.060 (3)0.094 (3)0.001 (2)0.013 (2)0.020 (2)
O40.056 (2)0.047 (2)0.078 (3)0.0057 (18)0.023 (2)0.015 (2)
O50.0328 (18)0.045 (2)0.081 (3)0.0064 (16)0.0025 (17)0.0121 (18)
O60.032 (2)0.061 (3)0.137 (4)0.0022 (18)0.002 (2)0.039 (3)
O70.027 (2)0.084 (3)0.184 (6)0.015 (2)0.005 (3)0.062 (4)
O80.072 (3)0.049 (2)0.062 (2)0.019 (2)0.014 (2)0.0153 (19)
N10.053 (3)0.043 (3)0.065 (3)0.009 (2)0.026 (2)0.011 (2)
N20.052 (3)0.041 (3)0.070 (3)0.009 (2)0.030 (2)0.010 (2)
N30.044 (2)0.044 (2)0.050 (3)0.0077 (19)0.002 (2)0.002 (2)
N40.046 (3)0.043 (2)0.048 (3)0.0108 (19)0.007 (2)0.004 (2)
C10.043 (3)0.051 (3)0.089 (5)0.001 (3)0.014 (3)0.012 (3)
C20.051 (3)0.044 (3)0.071 (4)0.004 (2)0.020 (3)0.004 (3)
C30.053 (3)0.057 (4)0.068 (4)0.002 (3)0.018 (3)0.009 (3)
C40.079 (4)0.040 (3)0.072 (4)0.007 (3)0.033 (3)0.005 (3)
C50.051 (3)0.041 (3)0.083 (4)0.007 (2)0.031 (3)0.003 (3)
C60.058 (3)0.041 (3)0.057 (3)0.007 (2)0.026 (3)0.011 (2)
C70.046 (3)0.041 (3)0.072 (4)0.002 (2)0.027 (3)0.003 (3)
C80.049 (3)0.048 (3)0.062 (3)0.015 (2)0.024 (3)0.006 (3)
C90.064 (4)0.051 (3)0.070 (4)0.012 (3)0.027 (3)0.016 (3)
C100.059 (4)0.080 (5)0.070 (4)0.018 (3)0.015 (3)0.015 (3)
C110.058 (4)0.077 (5)0.075 (4)0.005 (3)0.016 (3)0.004 (4)
C120.056 (4)0.058 (4)0.075 (4)0.006 (3)0.027 (3)0.003 (3)
C130.051 (3)0.047 (3)0.065 (4)0.014 (3)0.025 (3)0.007 (3)
C140.032 (3)0.050 (3)0.078 (4)0.001 (2)0.003 (3)0.010 (3)
C150.032 (3)0.043 (3)0.067 (3)0.003 (2)0.009 (2)0.014 (2)
C160.034 (3)0.058 (4)0.105 (5)0.000 (3)0.007 (3)0.029 (3)
C170.042 (3)0.060 (4)0.113 (5)0.006 (3)0.011 (3)0.032 (4)
C180.053 (3)0.043 (3)0.075 (4)0.006 (2)0.013 (3)0.014 (3)
C190.041 (3)0.040 (3)0.044 (3)0.007 (2)0.008 (2)0.002 (2)
C200.035 (3)0.041 (3)0.057 (3)0.001 (2)0.004 (2)0.004 (2)
C210.047 (3)0.047 (3)0.040 (3)0.015 (2)0.006 (2)0.001 (2)
C220.052 (3)0.052 (3)0.048 (3)0.012 (3)0.008 (3)0.001 (2)
C230.052 (3)0.069 (4)0.054 (3)0.000 (3)0.004 (3)0.007 (3)
C240.054 (4)0.102 (6)0.056 (4)0.024 (4)0.004 (3)0.004 (4)
C250.068 (4)0.072 (4)0.053 (4)0.027 (3)0.005 (3)0.012 (3)
C260.060 (4)0.052 (3)0.045 (3)0.022 (3)0.010 (3)0.005 (3)
C270.067 (4)0.050 (3)0.093 (5)0.000 (3)0.034 (4)0.010 (3)
C280.115 (6)0.058 (4)0.072 (4)0.034 (4)0.029 (4)0.027 (3)
C29A0.094 (9)0.072 (8)0.169 (11)0.039 (8)0.076 (8)0.039 (9)
C30A0.131 (8)0.090 (7)0.170 (10)0.039 (7)0.082 (8)0.031 (7)
C31A0.166 (9)0.112 (8)0.177 (10)0.046 (8)0.072 (8)0.026 (8)
C32A0.179 (13)0.136 (12)0.191 (13)0.041 (11)0.059 (12)0.024 (11)
C29B0.108 (8)0.070 (6)0.172 (10)0.041 (6)0.076 (7)0.049 (7)
C30B0.159 (8)0.098 (7)0.169 (9)0.035 (7)0.082 (7)0.028 (7)
C31B0.192 (10)0.125 (8)0.201 (11)0.032 (8)0.060 (8)0.036 (8)
C32B0.209 (13)0.143 (11)0.205 (13)0.020 (11)0.038 (11)0.053 (10)
C33A0.087 (7)0.095 (7)0.091 (6)0.017 (6)0.005 (5)0.029 (6)
C34A0.091 (7)0.097 (7)0.096 (6)0.012 (6)0.002 (6)0.014 (6)
C35A0.120 (9)0.119 (9)0.110 (8)0.002 (8)0.009 (8)0.004 (8)
C36A0.136 (11)0.129 (11)0.119 (10)0.009 (10)0.000 (9)0.010 (10)
C33B0.088 (7)0.098 (7)0.097 (6)0.021 (6)0.001 (6)0.023 (6)
C34B0.106 (7)0.105 (7)0.108 (7)0.007 (6)0.009 (6)0.023 (6)
C35B0.141 (10)0.114 (9)0.122 (9)0.006 (8)0.010 (8)0.026 (8)
C36B0.171 (12)0.130 (11)0.132 (11)0.011 (10)0.012 (11)0.028 (10)
Geometric parameters (Å, º) top
Sn1—O12.109 (3)C23—C241.375 (9)
Sn1—C29A2.112 (11)C23—H230.9500
Sn1—O52.116 (3)C24—C251.369 (9)
Sn1—C33B2.122 (10)C24—H240.9500
Sn1—C33A2.127 (10)C25—C261.385 (8)
Sn1—C29B2.139 (10)C25—H250.9500
Sn1—O62.517 (4)C27—H2710.9800
Sn1—O22.597 (4)C27—H2720.9800
Sn1—O7i3.192 (4)C27—H2730.9800
O1—C11.294 (7)C28—H2810.9800
O2—C11.246 (7)C28—H2820.9800
O3—C31.339 (7)C28—H2830.9800
O3—H30.8400C29A—C30A1.538 (8)
O4—C131.371 (6)C29A—H2910.9900
O4—C271.436 (7)C29A—H2920.9900
O5—C141.281 (6)C30A—C31A1.535 (8)
O6—C141.253 (6)C30A—H3010.9900
O7—C161.347 (7)C30A—H3020.9900
O7—H70.8400C31A—C32A1.539 (9)
O8—C261.353 (7)C31A—H3110.9900
O8—C281.439 (7)C31A—H3120.9900
N1—N21.261 (6)C32A—H3210.9800
N1—C61.406 (7)C32A—H3220.9800
N2—C81.427 (7)C32A—H3230.9800
N3—N41.261 (6)C29B—C30B1.556 (12)
N3—C191.426 (6)C29B—H2930.9900
N4—C211.418 (6)C29B—H2940.9900
C1—C21.478 (8)C30B—C31B1.517 (12)
C2—C71.386 (8)C30B—H3030.9900
C2—C31.415 (8)C30B—H3040.9900
C3—C41.395 (8)C31B—C32B1.560 (12)
C4—C51.342 (8)C31B—H3130.9900
C4—H40.9500C31B—H3140.9900
C5—C61.409 (8)C32B—H3240.9800
C5—H50.9500C32B—H3250.9800
C6—C71.390 (7)C32B—H3260.9800
C7—H710.9500C33A—C34A1.536 (9)
C8—C91.385 (7)C33A—H3310.9900
C8—C131.395 (8)C33A—H3320.9900
C9—C101.378 (8)C34A—C35A1.536 (8)
C9—H90.9500C34A—H3410.9900
C10—C111.382 (9)C34A—H3420.9900
C10—H100.9500C35A—C36A1.535 (8)
C11—C121.384 (9)C35A—H3510.9900
C11—H110.9500C35A—H3520.9900
C12—C131.373 (8)C36A—H3610.9800
C12—H120.9500C36A—H3620.9800
C14—C151.459 (7)C36A—H3630.9800
C15—C161.386 (7)C33B—C34B1.533 (12)
C15—C201.397 (7)C33B—H3330.9900
C16—C171.397 (8)C33B—H3340.9900
C17—C181.358 (8)C34B—C35B1.538 (12)
C17—H170.9500C34B—H3430.9900
C18—C191.393 (7)C34B—H3440.9900
C18—H180.9500C35B—C36B1.537 (12)
C19—C201.377 (7)C35B—H3530.9900
C20—H200.9500C35B—H3540.9900
C21—C221.392 (8)C36B—H3640.9800
C21—C261.405 (7)C36B—H3650.9800
C22—C231.377 (7)C36B—H3660.9800
C22—H220.9500
O1—Sn1—C29A105.5 (9)C23—C22—H22119.6
O1—Sn1—O581.84 (14)C21—C22—H22119.6
C29A—Sn1—O5113.0 (5)C24—C23—C22118.8 (6)
O1—Sn1—C33B103.6 (8)C24—C23—H23120.6
O5—Sn1—C33B99.3 (6)C22—C23—H23120.6
O1—Sn1—C33A102.9 (8)C25—C24—C23121.6 (6)
C29A—Sn1—C33A132.7 (11)C25—C24—H24119.2
O5—Sn1—C33A107.8 (6)C23—C24—H24119.2
O1—Sn1—C29B98.8 (6)C24—C25—C26120.5 (6)
O5—Sn1—C29B100.1 (4)C24—C25—H25119.7
C33B—Sn1—C29B152.2 (10)C26—C25—H25119.7
O1—Sn1—O6137.01 (13)O8—C26—C25125.0 (5)
C29A—Sn1—O690.9 (8)O8—C26—C21116.4 (5)
O5—Sn1—O655.23 (12)C25—C26—C21118.6 (6)
C33B—Sn1—O687.1 (6)O4—C27—H271109.5
C33A—Sn1—O693.3 (5)O4—C27—H272109.5
C29B—Sn1—O687.7 (6)H271—C27—H272109.5
O1—Sn1—O254.41 (13)O4—C27—H273109.5
C29A—Sn1—O281.8 (8)H271—C27—H273109.5
O5—Sn1—O2136.25 (13)H272—C27—H273109.5
C33B—Sn1—O292.3 (5)O8—C28—H281109.5
C33A—Sn1—O285.0 (5)O8—C28—H282109.5
C29B—Sn1—O287.3 (6)H281—C28—H282109.5
O6—Sn1—O2168.28 (13)O8—C28—H283109.5
O1—Sn1—O581.86 (13)H281—C28—H283109.5
O1—Sn1—O7i164.01 (13)H282—C28—H283109.5
C29A—Sn1—O7i69.4 (9)C30A—C29A—Sn1111.7 (12)
O5—Sn1—O7i114.15 (12)C30A—C29A—H291109.3
C33B—Sn1—O7i74.6 (9)Sn1—C29A—H291109.3
C33A—Sn1—O7i72.9 (9)C30A—C29A—H292109.3
C29B—Sn1—O7i79.3 (6)Sn1—C29A—H292109.3
O6—Sn1—O7i58.97 (12)H291—C29A—H292107.9
O2—Sn1—O7i109.60 (12)C31A—C30A—C29A120.7 (14)
C1—O1—Sn1103.8 (3)C31A—C30A—H301107.1
C1—O2—Sn182.2 (3)C29A—C30A—H301107.1
C3—O3—H3109.5C31A—C30A—H302107.1
C13—O4—C27117.1 (5)C29A—C30A—H302107.1
C14—O5—Sn1102.2 (3)H301—C30A—H302106.8
C14—O6—Sn184.2 (3)C30A—C31A—C32A102.6 (14)
C16—O7—Sn1i160.1 (4)C30A—C31A—H311111.3
C16—O7—H7109.5C32A—C31A—H311111.3
Sn1i—O7—H788.4C30A—C31A—H312111.3
C26—O8—C28117.7 (5)C32A—C31A—H312111.3
N2—N1—C6114.3 (4)H311—C31A—H312109.2
N1—N2—C8113.6 (4)C30B—C29B—Sn1112.7 (10)
N4—N3—C19113.2 (4)C30B—C29B—H293109.0
N3—N4—C21113.6 (4)Sn1—C29B—H293109.0
O2—C1—O1119.6 (5)C30B—C29B—H294109.0
O2—C1—C2122.4 (5)Sn1—C29B—H294109.0
O1—C1—C2118.0 (5)H293—C29B—H294107.8
C7—C2—C3119.8 (5)C31B—C30B—C29B122.5 (12)
C7—C2—C1120.4 (5)C31B—C30B—H303106.7
C3—C2—C1119.7 (5)C29B—C30B—H303106.7
O3—C3—C4119.3 (5)C31B—C30B—H304106.7
O3—C3—C2122.7 (5)C29B—C30B—H304106.7
C4—C3—C2118.0 (6)H303—C30B—H304106.6
C5—C4—C3122.2 (6)C30B—C31B—C32B102.4 (14)
C5—C4—H4118.9C30B—C31B—H313111.3
C3—C4—H4118.9C32B—C31B—H313111.3
C4—C5—C6120.4 (5)C30B—C31B—H314111.3
C4—C5—H5119.8C32B—C31B—H314111.3
C6—C5—H5119.8H313—C31B—H314109.2
C7—C6—N1124.2 (5)C31B—C32B—H324109.5
C7—C6—C5118.9 (5)C31B—C32B—H325109.5
N1—C6—C5116.9 (5)H324—C32B—H325109.5
C2—C7—C6120.7 (5)C31B—C32B—H326109.5
C2—C7—H71119.7H324—C32B—H326109.5
C6—C7—H71119.7H325—C32B—H326109.5
C9—C8—C13119.1 (5)C34A—C33A—Sn1112.5 (9)
C9—C8—N2123.7 (5)C34A—C33A—H331109.1
C13—C8—N2117.1 (5)Sn1—C33A—H331109.1
C10—C9—C8120.5 (6)C34A—C33A—H332109.1
C10—C9—H9119.7Sn1—C33A—H332109.1
C8—C9—H9119.7H331—C33A—H332107.8
C9—C10—C11120.0 (6)C35A—C34A—C33A106.3 (10)
C9—C10—H10120.0C35A—C34A—H341110.5
C11—C10—H10120.0C33A—C34A—H341110.5
C10—C11—C12119.9 (6)C35A—C34A—H342110.5
C10—C11—H11120.1C33A—C34A—H342110.5
C12—C11—H11120.1H341—C34A—H342108.7
C13—C12—C11120.2 (6)C36A—C35A—C34A110.1 (12)
C13—C12—H12119.9C36A—C35A—H351109.6
C11—C12—H12119.9C34A—C35A—H351109.6
O4—C13—C12123.8 (5)C36A—C35A—H352109.6
O4—C13—C8116.0 (5)C34A—C35A—H352109.6
C12—C13—C8120.2 (5)H351—C35A—H352108.2
O6—C14—O5118.4 (5)C34B—C33B—Sn1123.9 (13)
O6—C14—C15120.7 (5)C34B—C33B—H333106.4
O5—C14—C15120.9 (4)Sn1—C33B—H333106.4
C16—C15—C20118.9 (5)C34B—C33B—H334106.4
C16—C15—C14121.5 (5)Sn1—C33B—H334106.4
C20—C15—C14119.6 (4)H333—C33B—H334106.4
O7—C16—C15123.0 (5)C33B—C34B—C35B105.6 (12)
O7—C16—C17117.2 (5)C33B—C34B—H343110.6
C15—C16—C17119.8 (5)C35B—C34B—H343110.6
C18—C17—C16120.5 (5)C33B—C34B—H344110.6
C18—C17—H17119.7C35B—C34B—H344110.6
C16—C17—H17119.7H343—C34B—H344108.8
C17—C18—C19120.5 (5)C36B—C35B—C34B109.5 (12)
C17—C18—H18119.8C36B—C35B—H353109.8
C19—C18—H18119.8C34B—C35B—H353109.8
C20—C19—C18119.3 (5)C36B—C35B—H354109.8
C20—C19—N3115.9 (4)C34B—C35B—H354109.8
C18—C19—N3124.7 (5)H353—C35B—H354108.2
C19—C20—C15120.9 (5)C35B—C36B—H364109.5
C19—C20—H20119.5C35B—C36B—H365109.5
C15—C20—H20119.5H364—C36B—H365109.5
C22—C21—C26119.7 (5)C35B—C36B—H366109.5
C22—C21—N4124.0 (5)H364—C36B—H366109.5
C26—C21—N4116.3 (5)H365—C36B—H366109.5
C23—C22—C21120.8 (5)
C29A—Sn1—O1—C167.4 (7)N2—C8—C13—C12178.6 (5)
O5—Sn1—O1—C1179.1 (4)Sn1—O6—C14—O52.5 (5)
C33B—Sn1—O1—C183.3 (7)Sn1—O6—C14—C15176.0 (6)
C33A—Sn1—O1—C174.4 (7)Sn1—O5—C14—O63.0 (7)
C29B—Sn1—O1—C180.0 (6)Sn1—O5—C14—C15175.5 (5)
O6—Sn1—O1—C1176.2 (4)O6—C14—C15—C163.0 (10)
O2—Sn1—O1—C10.3 (4)O5—C14—C15—C16178.6 (6)
O1—Sn1—O2—C10.3 (4)O6—C14—C15—C20176.3 (6)
C29A—Sn1—O2—C1115.5 (8)O5—C14—C15—C202.1 (9)
O5—Sn1—O2—C10.6 (5)C20—C15—C16—O7179.5 (6)
C33B—Sn1—O2—C1105.4 (9)C14—C15—C16—O70.2 (11)
C33A—Sn1—O2—C1110.0 (10)C20—C15—C16—C170.2 (10)
C29B—Sn1—O2—C1102.5 (6)C14—C15—C16—C17179.4 (6)
O6—Sn1—O2—C1167.8 (8)O7—C16—C17—C18178.5 (7)
O1—Sn1—O5—C14176.0 (4)C15—C16—C17—C181.3 (11)
C29A—Sn1—O5—C1472.5 (11)C16—C17—C18—C191.0 (11)
C33B—Sn1—O5—C1481.4 (9)C17—C18—C19—C200.4 (9)
C33A—Sn1—O5—C1483.0 (9)C17—C18—C19—N3178.0 (6)
C29B—Sn1—O5—C1478.5 (7)N4—N3—C19—C20162.8 (5)
O6—Sn1—O5—C141.6 (4)N4—N3—C19—C1815.6 (7)
O2—Sn1—O5—C14175.3 (3)C18—C19—C20—C151.5 (8)
O1—Sn1—O6—C141.9 (5)N3—C19—C20—C15177.0 (5)
C29A—Sn1—O6—C14116.1 (7)C16—C15—C20—C191.2 (9)
O5—Sn1—O6—C141.6 (4)C14—C15—C20—C19178.1 (5)
C33B—Sn1—O6—C14105.0 (9)N3—N4—C21—C2210.1 (7)
C33A—Sn1—O6—C14111.0 (10)N3—N4—C21—C26173.3 (4)
C29B—Sn1—O6—C14102.4 (6)C26—C21—C22—C232.8 (8)
O2—Sn1—O6—C14167.6 (7)N4—C21—C22—C23179.3 (5)
C6—N1—N2—C8175.3 (4)C21—C22—C23—C241.1 (8)
C19—N3—N4—C21177.3 (4)C22—C23—C24—C250.9 (9)
Sn1—O2—C1—O10.4 (6)C23—C24—C25—C261.0 (10)
Sn1—O2—C1—C2179.9 (6)C28—O8—C26—C256.1 (8)
Sn1—O1—C1—O20.5 (7)C28—O8—C26—C21174.2 (5)
Sn1—O1—C1—C2179.8 (5)C24—C25—C26—O8179.6 (6)
O2—C1—C2—C7176.9 (6)C24—C25—C26—C210.7 (9)
O1—C1—C2—C73.4 (9)C22—C21—C26—O8177.7 (5)
O2—C1—C2—C31.9 (10)N4—C21—C26—O80.9 (7)
O1—C1—C2—C3177.7 (6)C22—C21—C26—C252.5 (8)
C7—C2—C3—O3177.9 (6)N4—C21—C26—C25179.3 (5)
C1—C2—C3—O31.0 (9)O1—Sn1—C29A—C30A92.9 (18)
C7—C2—C3—C40.9 (9)O5—Sn1—C29A—C30A5 (2)
C1—C2—C3—C4179.8 (5)C33A—Sn1—C29A—C30A142.2 (13)
O3—C3—C4—C5178.1 (6)O6—Sn1—C29A—C30A46.9 (18)
C2—C3—C4—C50.7 (9)O2—Sn1—C29A—C30A142.3 (18)
C3—C4—C5—C60.0 (9)Sn1—C29A—C30A—C31A60 (3)
N2—N1—C6—C724.0 (7)C29A—C30A—C31A—C32A179 (2)
N2—N1—C6—C5157.5 (5)O1—Sn1—C29B—C30B42.7 (14)
C4—C5—C6—C70.5 (8)O5—Sn1—C29B—C30B40.5 (14)
C4—C5—C6—N1178.0 (5)C33B—Sn1—C29B—C30B174.0 (13)
C3—C2—C7—C60.3 (8)O6—Sn1—C29B—C30B94.6 (13)
C1—C2—C7—C6179.2 (5)O2—Sn1—C29B—C30B96.1 (14)
N1—C6—C7—C2178.1 (5)Sn1—C29B—C30B—C31B173.6 (15)
C5—C6—C7—C20.4 (8)C29B—C30B—C31B—C32B178.5 (18)
N1—N2—C8—C928.8 (7)O1—Sn1—C33A—C34A123.3 (19)
N1—N2—C8—C13154.5 (5)C29A—Sn1—C33A—C34A111 (2)
C13—C8—C9—C101.1 (8)O5—Sn1—C33A—C34A38 (2)
N2—C8—C9—C10177.8 (5)O6—Sn1—C33A—C34A17 (2)
C8—C9—C10—C110.1 (9)O2—Sn1—C33A—C34A175 (2)
C9—C10—C11—C120.3 (10)Sn1—C33A—C34A—C35A178.5 (15)
C10—C11—C12—C130.3 (9)C33A—C34A—C35A—C36A179 (2)
C27—O4—C13—C126.8 (8)O1—Sn1—C33B—C34B47.2 (19)
C27—O4—C13—C8174.7 (5)O5—Sn1—C33B—C34B131.0 (17)
C11—C12—C13—O4179.7 (5)C29B—Sn1—C33B—C34B95 (3)
C11—C12—C13—C81.3 (8)O6—Sn1—C33B—C34B175.0 (19)
C9—C8—C13—O4179.7 (5)O2—Sn1—C33B—C34B6.7 (19)
N2—C8—C13—O42.9 (7)Sn1—C33B—C34B—C35B78 (2)
C9—C8—C13—C121.7 (8)C33B—C34B—C35B—C36B172.0 (17)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.932.613 (6)138
O7—H7···O60.842.012.603 (6)127
O7—H7···O6i0.842.392.871 (6)117
C22—H22···O8ii0.952.623.334 (7)134
C27—H271···O8ii0.982.623.449 (8)142
C27—H272···O4iii0.982.673.434 (8)136
C32B—H326···O3iv0.982.693.67 (2)170
C33B—H333···O7i0.992.643.33 (3)127
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1; (iv) x, y, z1/2.

Experimental details

Crystal data
Chemical formula[Sn2(C14H11N2O4)4(C4H9)4]
Mr1550.66
Crystal system, space groupMonoclinic, C2/c
Temperature (K)160
a, b, c (Å)35.6311 (7), 10.6333 (2), 19.5551 (4)
β (°) 104.0634 (11)
V3)7186.9 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.77
Crystal size (mm)0.20 × 0.20 × 0.15
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.805, 0.892
No. of measured, independent and
observed [I > 2σ(I)] reflections
70128, 6348, 4601
Rint0.104
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.148, 1.09
No. of reflections6347
No. of parameters524
No. of restraints147
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0562P)2 + 33.1175P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.73, 1.12

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
Sn1—O12.109 (3)Sn1—C29B2.139 (10)
Sn1—C29A2.112 (11)Sn1—O62.517 (4)
Sn1—O52.116 (3)Sn1—O22.597 (4)
Sn1—C33B2.122 (10)Sn1—O7i3.192 (4)
Sn1—C33A2.127 (10)
C29A—Sn1—C33A132.7 (11)O6—Sn1—O2168.28 (13)
O5—Sn1—O655.23 (12)O1—Sn1—O581.86 (13)
O1—Sn1—O254.41 (13)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.932.613 (6)138
O7—H7···O60.842.012.603 (6)127
O7—H7···O6i0.842.392.871 (6)117
C22—H22···O8ii0.952.623.334 (7)134
C27—H271···O8ii0.982.623.449 (8)142
C27—H272···O4iii0.982.673.434 (8)136
C32B—H326···O3iv0.982.693.67 (2)170
C33B—H333···O7i0.992.643.33 (3)127
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1; (iv) x, y, z1/2.
 

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