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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 6| June 2012| Pages m854-m855
doi:10.1107/S1600536812021125

Di­benzyl­aza­nium (oxalato-κ2O,O′)tri­phenyl­stannate(IV)

Ndongo Gueye,a Libasse Diop,a* Kieran C. Molloyb and Gabrielle Kociok-Köhnb

aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bDepartment of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, England
*Correspondence e-mail: dlibasse@gmail.com

(Received 3 March 2012; accepted 9 May 2012; online 31 May 2012)

The title compound, (C14H16N)[Sn(C6H5)3(C2O2)], was synthesised by allowing C2O4(Bz2NH2)2 (Bz = benzyl) to react with SnPh3Cl. The asymmetric unit is built up by four SnPh3C2O4 anions and four Bz2NH2 cations which are related by a pseudo-inversion centre. Each SnIV cation is five-coordinated by the three phenyl groups and two O atoms belonging to the chelating oxalate ligand; the coordination geometry is that of a distorted trigonal bipyramid. Anions and cations are linked through N—H⋯O hydrogen bonds into a layer structure parallel to (001). Moreover, the anion–cation pairs are associated by two bifurcated N—H⋯O hydrogen bonds, generating pseudo-dimers. One of the phenyl groups of one anion is disordered over two sets of sites in a 0.69:0.31 ratio. The Flack parameter value of 0.44 (1) indicates racemic twinning.

Related literature

For related structures, see: Ng & Rae (2000[Ng, S. W. & Rae, A. D. (2000). Z. Kristallogr. 215, 199-204.]); Ng & Hook (1999[Ng, S. W. & Hook, J. M. (1999). Acta Cryst. C55, 310-312.]); Ng & Kumar Das (1995[Ng, S. W. & Kumar Das, V. G. (1995). Acta Cryst. C51, 2489-2491.]). For general background, see: Evans & Karpel (1985[Evans, J. C. & Karpel, S. (1985). In Organotin Compounds in Modern Technology. Amsterdam: Elsevier.]).

[Scheme 1]

Experimental

Crystal data

  • (C14H16N)[Sn(C6H5)3(C2O2)]

  • Mr = 636.31

  • Triclinic, P 1

  • a = 9.8575 (2) Å

  • b = 16.8894 (3) Å

  • c = 18.9812 (4) Å

  • α = 110.444 (1)°

  • β = 96.082 (1)°

  • γ = 93.384 (1)°

  • V = 2928.73 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.91 mm−1

  • T = 150 K

  • 0.40 × 0.20 × 0.10 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.712, Tmax = 0.914

  • 56750 measured reflections

  • 22478 independent reflections

  • 20136 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.070

  • S = 1.06

  • 22474 reflections

  • 1424 parameters

  • 15 restraints

  • H-atom parameters constrained

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.86 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 10508 Fridel pairs

  • Flack parameter: 0.438 (10)

Table 1
Selected bond lengths (Å)

Sn1—O1 2.124 (3)
Sn1—C121 2.131 (4)
Sn1—C111 2.156 (4)
Sn1—C131 2.160 (4)
Sn1—O2 2.306 (3)
Sn2—O6 2.116 (3)
Sn2—C221 2.131 (5)
Sn2—C211 2.147 (4)
Sn2—C231 2.167 (4)
Sn2—O5 2.317 (3)
Sn3—O9 2.104 (3)
Sn3—C311 2.142 (4)
Sn3—C321 2.142 (4)
Sn3—C331 2.185 (4)
Sn3—O10 2.355 (3)
Sn4—O13 2.117 (3)
Sn4—C421 2.133 (4)
Sn4—C411 2.140 (4)
Sn4—C431 2.168 (4)
Sn4—O14 2.289 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O4 0.92 1.94 2.847 (4) 171
N1—H1B⋯O15 0.92 2.26 2.902 (4) 126
N1—H1B⋯O16 0.92 1.98 2.805 (4) 148
N2—H2A⋯O7 0.92 1.92 2.795 (4) 159
N2—H2B⋯O11 0.92 2.05 2.857 (4) 146
N2—H2B⋯O12 0.92 2.27 2.925 (4) 128
N3—H3A⋯O7 0.92 2.21 2.951 (4) 137
N3—H3A⋯O8 0.92 2.08 2.813 (4) 136
N3—H3B⋯O11 0.92 1.91 2.816 (4) 169
N4—H4A⋯O3 0.92 2.15 2.843 (4) 131
N4—H4A⋯O4 0.92 2.10 2.843 (4) 137
N4—H4B⋯O16 0.92 1.84 2.755 (4) 177

Data collection: COLLECT (Nonius, 1997[Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812021125/kp2394sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021125/kp2394Isup2.hkl

checkCIF report


Comment top

New organotin (IV) compounds are of interest because of their physical applications (Evans & Karpel, 1985). The X-ray structure of C2O4SnPh3Cy2NH2 were reported by (Ng & Kumar Das, 1995; Ng & Hook, 1999; Ng & Rae, 2000); it consists of two [C2O4SnPh3]- anions connected into dimers by identical N—H—O hydrogen bonds. We have modified the counter ion by using Bz2NH2.

The asymmetric unit is build up by the association of four C2O4SnPh3 anions and four Bz2NH2 cations (Fig. 1, Table 1). In each anion, the oxalate ion chelates the SnPh3 residue. Sn atoms are in pentagonal environments. Anion and cation are linked by N—H···O hydrogen bonds. Moreover, anion and cation pairs are associated by two bifurcated N—H···O hydrogen bonds into a pseudo dimer (Table 2, Fig. 1). The type of dimers observed in the title compound is different from the one reported by Ng & Rae (2000). The Sn—O bonds (Table 1) indicate asymmetrical chelation.

Related literature top

For related structures, see: Ng & Rae (2000); Ng & Hook (1999); Ng & Kumar Das (1995). For general background, see: Evans & Karpel (1985).

Experimental top

When an ethanolic solution of (Bz2NH2)2C2O4 is mixed with a similar solution of SnPh3Cl in 1/2 ratio, crystals of Bz2NH2C2O4SnPh3 suitable for X-ray work were obtained after slow evaporation.

All the chemicals were from ALDRICH and used without any further purification.

Refinement top

All H atoms attached to C and N atoms were fixed geometrically and treated as riding with C—H = 0.98 Å (methyl) or 0.97 Å (methylene) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(C or N).

One of the phenyl group attached to Sn2 is disordered over two positions by rotation around the central C—C axis with occupancy factor in the ratio 0.69/0.31. The C—C distances and C—C—C angles were restrained to reasonable dimensions by using the SAME instruction available within SHELXL97 (Sheldrick, 2008). The anistropic thermal parameters were severely restrained using the EADP instruction.

The value of the Flack's parameters is indicative of a twin by inversion (racemic twinning). Although, ADDSYM within PLATON (Spek, 2009) detects (pseudo) centre of symmetry, no model could be correctly refined in the centrosymmetric P1 space group.

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the unit cell with the atom numbering scheme. Ellipsoids are drawn at the 30% probability level. H atoms are drawn as small spheres of arbitrary radii. N—H···O hydrogen bonds are represented by dashed lines. H atoms attached to C atoms have been omitted for the sake of clarity.
Dibenzylazanium (oxalato-κ2O,O')triphenylstannate(IV) top
Crystal data top
(C14H16N)[Sn(C6H5)3(C2O2)]Z = 4
Mr = 636.31F(000) = 1296
Triclinic, P1Dx = 1.443 Mg m−3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8575 (2) ÅCell parameters from 70274 reflections
b = 16.8894 (3) Åθ = 2.9–27.5°
c = 18.9812 (4) ŵ = 0.91 mm−1
α = 110.444 (1)°T = 150 K
β = 96.082 (1)°Block, colourless
γ = 93.384 (1)°0.40 × 0.20 × 0.10 mm
V = 2928.73 (10) Å3
Data collection top
Nonius KappaCCD
diffractometer		22478 independent reflections
Radiation source: fine-focus sealed tube20136 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
305 2.0 degree images with ϕ and ω scansθmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)		h = −12→12
Tmin = 0.712, Tmax = 0.914k = −21→21
56750 measured reflectionsl = −23→23
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)] = 0.031H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0332P)2 + 0.514P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.007
22474 reflectionsΔρmax = 0.61 e Å−3
1424 parametersΔρmin = −0.86 e Å−3
15 restraintsAbsolute structure: Flack (1983), with 10508 Fridel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.438 (10)
Crystal data top
(C14H16N)[Sn(C6H5)3(C2O2)]γ = 93.384 (1)°
Mr = 636.31V = 2928.73 (10) Å3
Triclinic, P1Z = 4
a = 9.8575 (2) ÅMo Kα radiation
b = 16.8894 (3) ŵ = 0.91 mm−1
c = 18.9812 (4) ÅT = 150 K
α = 110.444 (1)°0.40 × 0.20 × 0.10 mm
β = 96.082 (1)°
Data collection top
Nonius KappaCCD
diffractometer		22478 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)		20136 reflections with I > 2σ(I)
Tmin = 0.712, Tmax = 0.914Rint = 0.038
56750 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.070Δρmax = 0.61 e Å−3
S = 1.06Δρmin = −0.86 e Å−3
22474 reflectionsAbsolute structure: Flack (1983), with 10508 Fridel pairs
1424 parametersAbsolute structure parameter: 0.438 (10)
15 restraints
Special details top

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)
Sn10.03511 (2)0.316679 (15)−0.230967 (14)0.02958 (7)
O10.0397 (4)0.31295 (18)−0.12006 (15)0.0379 (8)
O20.1278 (3)0.44817 (18)−0.14581 (15)0.0324 (7)
O30.0906 (3)0.37964 (18)0.00463 (15)0.0409 (8)
O40.1723 (3)0.52393 (17)−0.02096 (14)0.0348 (7)
C10.0845 (4)0.3788 (3)−0.0606 (2)0.0295 (9)
C20.1337 (4)0.4575 (3)−0.0767 (2)0.0287 (9)
C111−0.0942 (4)0.3882 (3)−0.2797 (2)0.0350 (10)
C112−0.1393 (5)0.4646 (3)−0.2382 (2)0.0434 (11)
H112−0.11630.4872−0.18460.052*
C113−0.2174 (6)0.5085 (4)−0.2740 (3)0.0560 (14)
H113−0.24660.5614−0.24520.067*
C114−0.2527 (5)0.4753 (3)−0.3514 (3)0.0479 (13)
H114−0.30850.5048−0.37570.058*
C115−0.2086 (5)0.4003 (3)−0.3938 (2)0.0420 (11)
H115−0.23130.3784−0.44750.050*
C116−0.1304 (5)0.3568 (3)−0.3578 (2)0.0376 (10)
H116−0.10080.3042−0.38710.045*
C1210.2246 (4)0.2965 (3)−0.2760 (2)0.0313 (9)
C1220.3270 (4)0.3617 (3)−0.2628 (2)0.0353 (9)
H1220.31840.4170−0.22820.042*
C1230.4429 (4)0.3470 (3)−0.3001 (2)0.0407 (10)
H1230.51140.3925−0.29160.049*
C1240.4588 (4)0.2668 (3)−0.3493 (2)0.0405 (10)
H1240.53780.2574−0.37460.049*
C1250.3596 (5)0.2003 (3)−0.3617 (2)0.0405 (11)
H1250.37080.1447−0.39470.049*
C1260.2429 (4)0.2153 (3)−0.3252 (2)0.0341 (9)
H1260.17460.1695−0.33400.041*
C131−0.0762 (4)0.1924 (3)−0.2639 (2)0.0351 (10)
C132−0.0249 (5)0.1319 (3)−0.2359 (3)0.0454 (11)
H1320.06240.1451−0.20580.054*
C133−0.0962 (6)0.0543 (3)−0.2504 (3)0.0574 (14)
H133−0.05790.0141−0.23150.069*
C134−0.2278 (6)0.0351 (4)−0.2941 (3)0.0615 (16)
H134−0.2802−0.0175−0.30330.074*
C135−0.2790 (5)0.0929 (4)−0.3229 (3)0.0606 (16)
H135−0.36600.0792−0.35340.073*
C136−0.2054 (5)0.1713 (3)−0.3080 (2)0.0446 (12)
H136−0.24330.2108−0.32800.054*
N10.2842 (3)0.6970 (2)0.03179 (18)0.0317 (8)
H1A0.24950.64090.00950.038*
H1B0.25050.71890.07730.038*
C1410.2338 (4)0.7433 (3)−0.0179 (3)0.0452 (11)
H14A0.25790.7150−0.06950.054*
H14B0.27900.80220.00220.054*
C1420.0808 (5)0.7450 (3)−0.0220 (3)0.0410 (11)
C143−0.0076 (4)0.6755 (3)−0.0680 (2)0.0452 (10)
H1430.02870.6256−0.09770.054*
C144−0.1499 (5)0.6772 (3)−0.0716 (3)0.0511 (12)
H144−0.20970.6283−0.10240.061*
C145−0.2023 (5)0.7502 (3)−0.0301 (3)0.0467 (11)
H145−0.29870.7526−0.03430.056*
C146−0.1171 (5)0.8191 (3)0.0168 (3)0.0518 (12)
H146−0.15480.86850.04620.062*
C1470.0254 (5)0.8178 (3)0.0222 (3)0.0474 (11)
H1470.08420.86580.05560.057*
C1510.4385 (4)0.7016 (3)0.0473 (2)0.0379 (9)
H15A0.48010.75310.04100.045*
H15B0.46580.70620.10040.045*
C1520.4914 (4)0.6244 (2)−0.0056 (2)0.0339 (9)
C1530.4914 (4)0.6112 (3)−0.0820 (2)0.0389 (9)
H1530.45940.6525−0.10140.047*
C1540.5374 (5)0.5387 (3)−0.1303 (3)0.0484 (11)
H1540.53400.5294−0.18280.058*
C1550.5891 (5)0.4787 (3)−0.1013 (3)0.0522 (13)
H1550.62120.4293−0.13450.063*
C1560.5939 (5)0.4905 (3)−0.0262 (3)0.0462 (13)
H1560.63020.4502−0.00670.055*
C1570.5434 (5)0.5641 (3)0.0222 (3)0.0451 (11)
H1570.54490.57270.07450.054*
Sn20.51794 (2)0.821131 (14)−0.203097 (14)0.02842 (7)
O50.6317 (3)0.94752 (18)−0.11733 (15)0.0324 (7)
O60.4827 (3)0.82714 (17)−0.09338 (15)0.0313 (6)
O70.6615 (3)1.02853 (17)0.00613 (15)0.0350 (7)
O80.5115 (3)0.90160 (17)0.03147 (15)0.0393 (7)
C30.6163 (4)0.9635 (3)−0.0487 (2)0.0273 (9)
C40.5301 (4)0.8937 (2)−0.0336 (2)0.0293 (9)
C2110.4038 (4)0.8984 (3)−0.2516 (2)0.0275 (9)
C2120.4369 (5)0.9847 (3)−0.2329 (2)0.0366 (10)
H2120.51271.0135−0.19550.044*
C2130.3593 (5)1.0289 (3)−0.2688 (2)0.0434 (11)
H2130.38231.0882−0.25530.052*
C2140.2509 (5)0.9891 (3)−0.3230 (3)0.0454 (12)
H2140.19811.0204−0.34660.055*
C2150.2183 (5)0.9027 (3)−0.3433 (3)0.0472 (12)
H2150.14430.8740−0.38210.057*
C2160.2929 (4)0.8583 (3)−0.3074 (2)0.0376 (10)
H2160.26860.7992−0.32090.045*
C2210.7107 (5)0.7938 (3)−0.2423 (3)0.0529 (6)
C2220.8358 (6)0.8395 (4)−0.2051 (4)0.0529 (6)0.69
H2220.83850.8827−0.15660.063*0.69
C2230.9568 (7)0.8237 (4)−0.2366 (4)0.0529 (6)0.69
H2231.04150.8554−0.21070.063*0.69
C2240.9496 (5)0.7584 (3)−0.3092 (3)0.0529 (6)
H2241.03050.7461−0.33230.063*
C2250.8344 (7)0.7162 (5)−0.3435 (4)0.0529 (6)0.69
H2250.83190.6715−0.39100.063*0.69
C2260.7128 (7)0.7346 (5)−0.3127 (4)0.0529 (6)0.69
H2260.62870.7049−0.34160.063*0.69
C22A0.7841 (14)0.8550 (8)−0.2558 (9)0.0529 (6)0.31
H22A0.75600.9107−0.24020.063*0.31
C23A0.8994 (13)0.8392 (8)−0.2916 (9)0.0529 (6)0.31
H23A0.94510.8822−0.30460.063*0.31
C25A0.8550 (14)0.6933 (9)−0.3205 (9)0.0529 (6)0.31
H25A0.86520.6376−0.35370.063*0.31
C26A0.7398 (14)0.7101 (8)−0.2814 (9)0.0529 (6)0.31
H26A0.68020.6638−0.28140.063*0.31
C2320.4246 (5)0.6248 (3)−0.2878 (3)0.0551 (12)
H2320.51370.6217−0.30270.066*
C2330.3315 (7)0.5507 (3)−0.3122 (3)0.0706 (16)
H2330.35840.4986−0.34430.085*
C2310.3876 (5)0.7020 (3)−0.2424 (2)0.0336 (10)
C2340.2061 (6)0.5523 (3)−0.2910 (3)0.0587 (15)
H2340.14530.5017−0.30700.070*
C2350.1663 (5)0.6278 (3)−0.2459 (3)0.0580 (13)
H2350.07700.6298−0.23120.070*
C2360.2559 (5)0.7009 (3)−0.2218 (2)0.0480 (11)
H2360.22680.7524−0.19010.058*
N20.8261 (3)1.1797 (2)0.03425 (17)0.0279 (7)
H2A0.77741.12690.01300.034*
H2B0.78271.21160.07360.034*
C2410.8219 (4)1.2206 (3)−0.0240 (2)0.0364 (10)
H24A0.86071.1838−0.06870.044*
H24B0.88041.2755−0.00290.044*
C2420.6781 (4)1.2363 (2)−0.0495 (2)0.0302 (9)
C2430.5821 (4)1.2618 (3)−0.0002 (2)0.0385 (10)
H2430.60411.26740.05140.046*
C2440.4554 (4)1.2789 (3)−0.0252 (2)0.0442 (10)
H2440.39001.29600.00920.053*
C2450.4223 (5)1.2715 (3)−0.1000 (2)0.0425 (11)
H2450.33451.2831−0.11740.051*
C2460.5183 (5)1.2470 (3)−0.1487 (2)0.0435 (12)
H2460.49711.2425−0.20010.052*
C2470.6455 (5)1.2287 (3)−0.1238 (2)0.0367 (10)
H2470.71051.2109−0.15820.044*
C2510.9683 (4)1.1697 (3)0.0660 (2)0.0381 (10)
H25B1.02191.22630.08780.046*
H25C0.96141.14770.10760.046*
C2521.0434 (4)1.1110 (3)0.0078 (2)0.0377 (10)
C2531.1379 (4)1.1420 (3)−0.0284 (2)0.0411 (10)
H2531.15361.2014−0.01720.049*
C2541.2092 (5)1.0870 (3)−0.0804 (3)0.0487 (11)
H2541.27231.1084−0.10550.058*
C2551.1883 (6)1.0020 (3)−0.0952 (3)0.0640 (16)
H2551.23630.9639−0.13120.077*
C2561.0987 (7)0.9712 (3)−0.0585 (4)0.081 (2)
H2561.08650.9120−0.06800.097*
C2571.0256 (6)1.0260 (3)−0.0074 (3)0.0594 (15)
H2570.96251.00400.01730.071*
Sn30.85092 (2)1.406077 (13)0.386037 (12)0.02407 (6)
O90.8803 (3)1.40967 (17)0.27899 (14)0.0294 (6)
O100.7281 (3)1.28399 (18)0.29295 (15)0.0300 (7)
O110.6933 (3)1.21442 (17)0.16696 (14)0.0313 (6)
O120.8453 (3)1.34779 (18)0.15305 (15)0.0361 (7)
C50.7414 (4)1.2751 (2)0.2254 (2)0.0260 (9)
C60.8298 (4)1.3492 (2)0.2162 (2)0.0265 (9)
C3110.9559 (4)1.3190 (3)0.4257 (2)0.0253 (8)
C3120.8974 (4)1.2365 (2)0.4124 (2)0.0330 (9)
H3120.81231.21580.38050.040*
C3130.9627 (5)1.1844 (3)0.4456 (2)0.0377 (10)
H3130.92211.12870.43640.045*
C3141.0868 (5)1.2143 (3)0.4920 (2)0.0394 (10)
H3141.13181.17910.51460.047*
C3151.1453 (5)1.2958 (3)0.5053 (2)0.0393 (10)
H3151.23021.31650.53740.047*
C3161.0811 (4)1.3465 (3)0.4724 (2)0.0332 (9)
H3161.12331.40190.48170.040*
C3210.6560 (4)1.4362 (2)0.4228 (2)0.0209 (7)
C3220.5410 (4)1.3769 (2)0.4038 (2)0.0307 (8)
H3220.54531.32050.37020.037*
C3230.4195 (5)1.3997 (3)0.4336 (3)0.0433 (10)
H3230.34181.35890.42080.052*
C3240.4128 (5)1.4825 (3)0.4821 (3)0.0429 (10)
H3240.32961.49850.50150.052*
C3250.5265 (4)1.5416 (3)0.5023 (2)0.0355 (9)
H3250.52131.59780.53610.043*
C3260.6476 (4)1.5196 (2)0.4737 (2)0.0309 (8)
H3260.72541.56060.48820.037*
C3310.9827 (4)1.5259 (2)0.4361 (2)0.0290 (9)
C3321.0369 (4)1.5553 (2)0.5134 (2)0.0332 (9)
H3321.00881.52550.54440.040*
C3331.1308 (4)1.6272 (2)0.5454 (2)0.0393 (9)
H3331.16891.64500.59720.047*
C3341.1684 (5)1.6728 (3)0.5014 (2)0.0425 (10)
H3341.23251.72190.52290.051*
C3351.1121 (5)1.6464 (3)0.4251 (2)0.0454 (11)
H3351.13661.67810.39490.054*
C3361.0212 (4)1.5746 (2)0.3939 (2)0.0385 (9)
H3360.98331.55750.34210.046*
N30.5244 (3)1.0645 (2)0.14328 (17)0.0274 (7)
H3A0.56291.02640.10500.033*
H3B0.57281.11690.15570.033*
C3410.5384 (5)1.0388 (3)0.2101 (3)0.0473 (11)
H34A0.47230.98840.20030.057*
H34B0.51411.08530.25420.057*
C3420.6799 (4)1.0180 (2)0.2298 (2)0.0336 (9)
C3430.7847 (5)1.0171 (3)0.1869 (3)0.0500 (11)
H3430.76941.03140.14270.060*
C3440.9129 (5)0.9954 (3)0.2080 (3)0.0553 (12)
H3440.98440.99480.17800.066*
C3450.9365 (6)0.9748 (3)0.2718 (3)0.0539 (13)
H3451.02390.95980.28590.065*
C3460.8325 (6)0.9762 (3)0.3150 (3)0.0525 (14)
H3460.84860.96230.35940.063*
C3470.7045 (5)0.9976 (3)0.2945 (2)0.0442 (11)
H3470.63350.99830.32480.053*
C3510.3787 (4)1.0692 (3)0.1144 (2)0.0418 (11)
H35A0.32491.01410.10450.050*
H35B0.37631.07840.06560.050*
C3520.3116 (4)1.1397 (3)0.1693 (2)0.0317 (9)
C3530.2290 (5)1.1208 (3)0.2162 (3)0.0506 (12)
H3530.21661.06440.21560.061*
C3540.1631 (5)1.1844 (4)0.2648 (3)0.0583 (14)
H3540.10561.17120.29710.070*
C3550.1815 (5)1.2673 (3)0.2660 (3)0.0558 (14)
H3550.13631.31080.29880.067*
C3560.2653 (5)1.2856 (3)0.2195 (3)0.0525 (12)
H3560.27851.34190.21970.063*
C3570.3301 (5)1.2223 (3)0.1724 (3)0.0421 (11)
H3570.38961.23590.14110.050*
Sn40.30006 (2)0.902830 (14)0.390075 (15)0.02991 (7)
O130.3061 (4)0.91751 (18)0.28409 (16)0.0421 (8)
O140.2218 (4)0.77437 (19)0.29757 (17)0.0409 (8)
O150.2848 (4)0.85576 (19)0.15774 (16)0.0480 (8)
O160.2088 (3)0.70374 (18)0.17199 (16)0.0424 (8)
C70.2770 (5)0.8537 (3)0.2211 (2)0.0365 (10)
C80.2312 (4)0.7689 (3)0.2306 (2)0.0361 (10)
C4110.4296 (4)0.8326 (3)0.4386 (2)0.0323 (9)
C4120.4817 (5)0.7565 (3)0.3978 (3)0.0408 (11)
H4120.45660.73070.34450.049*
C4130.5695 (5)0.7199 (3)0.4359 (3)0.0525 (13)
H4130.60620.66940.40790.063*
C4140.6053 (5)0.7541 (3)0.5128 (3)0.0524 (13)
H4140.66610.72760.53770.063*
C4150.5516 (5)0.8285 (3)0.5546 (3)0.0479 (12)
H4150.57430.85260.60820.057*
C4160.4648 (5)0.8668 (3)0.5165 (2)0.0393 (10)
H4160.42880.91750.54460.047*
C4210.1064 (4)0.9153 (2)0.4312 (2)0.0289 (9)
C4220.0038 (5)0.8460 (3)0.4094 (3)0.0437 (11)
H4220.01360.79490.36930.052*
C423−0.1107 (5)0.8526 (3)0.4465 (3)0.0519 (12)
H423−0.17950.80590.43180.062*
C424−0.1257 (5)0.9276 (3)0.5054 (3)0.0478 (12)
H424−0.20380.93140.53130.057*
C425−0.0284 (5)0.9955 (3)0.5261 (2)0.0415 (11)
H425−0.04031.04720.56520.050*
C4260.0887 (4)0.9889 (3)0.4896 (2)0.0342 (9)
H4260.15721.03590.50520.041*
C4310.4099 (4)1.0288 (3)0.4305 (2)0.0291 (9)
C4320.5422 (4)1.0466 (3)0.4709 (2)0.0336 (9)
H4320.58081.00470.48710.040*
C4330.6181 (5)1.1241 (3)0.4876 (2)0.0425 (11)
H4330.70801.13500.51470.051*
C4340.5614 (5)1.1856 (3)0.4643 (3)0.0462 (12)
H4340.61261.23900.47560.055*
C4350.4312 (5)1.1696 (3)0.4251 (3)0.0466 (11)
H4350.39281.21170.40900.056*
C4360.3563 (4)1.0919 (3)0.4090 (2)0.0376 (10)
H4360.26581.08180.38260.045*
N40.0827 (3)0.5401 (2)0.12048 (17)0.0285 (7)
H4A0.12510.51040.07970.034*
H4B0.12250.59540.13890.034*
C441−0.0675 (4)0.5394 (3)0.0929 (2)0.0357 (9)
H44A−0.07580.54620.04300.043*
H44B−0.11620.48360.08590.043*
C442−0.1352 (4)0.6083 (3)0.1467 (2)0.0347 (9)
C443−0.1991 (5)0.5956 (3)0.2029 (3)0.0459 (11)
H443−0.19880.54240.20940.055*
C444−0.2648 (6)0.6601 (3)0.2510 (3)0.0612 (14)
H444−0.30700.65110.29070.073*
C445−0.2681 (6)0.7352 (3)0.2408 (3)0.0619 (15)
H445−0.31480.77850.27260.074*
C446−0.2035 (5)0.7496 (3)0.1839 (3)0.0569 (14)
H446−0.20490.80290.17740.068*
C447−0.1380 (5)0.6865 (3)0.1376 (3)0.0448 (11)
H447−0.09390.69610.09880.054*
C4510.1085 (5)0.5034 (3)0.1800 (2)0.0427 (11)
H45A0.05830.44590.16250.051*
H45B0.07210.53890.22620.051*
C4520.2580 (5)0.4972 (3)0.2000 (2)0.0343 (10)
C4530.3424 (5)0.4641 (3)0.1453 (2)0.0494 (11)
H4530.30790.44900.09310.059*
C4540.4784 (5)0.4526 (3)0.1662 (3)0.0500 (12)
H4540.53610.43050.12840.060*
C4550.5284 (5)0.4735 (3)0.2417 (2)0.0430 (10)
H4550.62000.46500.25620.052*
C4560.4440 (5)0.5069 (3)0.2962 (2)0.0442 (10)
H4560.47830.52150.34840.053*
C4570.3104 (4)0.5193 (2)0.2759 (2)0.0390 (9)
H4570.25410.54310.31410.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02638 (14)0.03560 (15)0.02377 (12)0.00268 (11)0.00207 (11)0.00741 (11)
O10.051 (2)0.0324 (16)0.0241 (14)−0.0054 (15)0.0007 (14)0.0058 (12)
O20.0372 (17)0.0344 (15)0.0231 (14)−0.0007 (13)0.0020 (12)0.0086 (12)
O30.057 (2)0.0345 (15)0.0275 (14)−0.0050 (14)0.0032 (14)0.0091 (12)
O40.0408 (16)0.0277 (14)0.0277 (13)−0.0060 (12)0.0033 (12)0.0018 (12)
C10.029 (2)0.031 (2)0.0222 (18)−0.0008 (17)0.0004 (16)0.0041 (16)
C20.0222 (19)0.028 (2)0.033 (2)0.0018 (16)0.0028 (18)0.0083 (18)
C1110.026 (2)0.042 (3)0.035 (2)0.0016 (19)0.0020 (19)0.0133 (19)
C1120.037 (2)0.060 (3)0.030 (2)0.020 (2)0.0055 (19)0.010 (2)
C1130.055 (3)0.070 (3)0.044 (3)0.034 (3)0.011 (2)0.016 (2)
C1140.040 (3)0.067 (3)0.047 (3)0.021 (2)0.005 (2)0.032 (3)
C1150.041 (3)0.059 (3)0.027 (2)0.004 (2)0.0038 (19)0.018 (2)
C1160.043 (2)0.042 (2)0.0263 (19)0.006 (2)0.0044 (19)0.0109 (17)
C1210.031 (2)0.040 (2)0.0234 (18)0.0061 (18)−0.0009 (17)0.0120 (17)
C1220.037 (2)0.034 (2)0.033 (2)0.0027 (18)0.0073 (18)0.0088 (17)
C1230.033 (2)0.047 (3)0.046 (2)−0.0022 (19)0.007 (2)0.022 (2)
C1240.031 (2)0.058 (3)0.032 (2)0.010 (2)0.0083 (18)0.012 (2)
C1250.038 (2)0.048 (3)0.031 (2)0.013 (2)0.0037 (19)0.0075 (18)
C1260.031 (2)0.037 (2)0.031 (2)0.0062 (18)0.0053 (18)0.0073 (17)
C1310.027 (2)0.045 (3)0.025 (2)−0.0036 (19)0.0055 (18)0.0020 (18)
C1320.041 (3)0.046 (3)0.044 (2)−0.004 (2)−0.001 (2)0.013 (2)
C1330.062 (3)0.045 (3)0.058 (3)−0.013 (3)0.004 (3)0.013 (2)
C1340.059 (3)0.058 (3)0.048 (3)−0.029 (3)0.008 (3)0.000 (3)
C1350.040 (3)0.081 (4)0.039 (3)−0.024 (3)0.002 (2)0.001 (3)
C1360.035 (2)0.059 (3)0.030 (2)−0.006 (2)0.003 (2)0.005 (2)
N10.0311 (17)0.0313 (17)0.0300 (16)−0.0017 (14)0.0068 (14)0.0075 (14)
C1410.035 (2)0.054 (3)0.056 (3)0.000 (2)0.008 (2)0.031 (2)
C1420.038 (2)0.044 (3)0.049 (2)0.002 (2)0.010 (2)0.026 (2)
C1430.041 (2)0.040 (2)0.048 (2)0.0052 (19)0.005 (2)0.009 (2)
C1440.042 (3)0.048 (3)0.053 (3)0.001 (2)−0.002 (2)0.008 (2)
C1450.037 (2)0.049 (3)0.059 (3)0.007 (2)0.005 (2)0.025 (2)
C1460.050 (3)0.037 (2)0.071 (3)0.010 (2)0.014 (2)0.021 (2)
C1470.047 (3)0.035 (2)0.059 (3)−0.001 (2)0.003 (2)0.018 (2)
C1510.029 (2)0.042 (2)0.037 (2)−0.0007 (17)−0.0005 (17)0.0093 (18)
C1520.027 (2)0.032 (2)0.041 (2)−0.0034 (17)0.0006 (18)0.0126 (18)
C1530.038 (2)0.039 (2)0.040 (2)0.0020 (18)0.0037 (18)0.0165 (18)
C1540.048 (3)0.051 (3)0.042 (2)0.004 (2)0.010 (2)0.010 (2)
C1550.042 (3)0.035 (2)0.071 (3)0.001 (2)0.013 (3)0.006 (2)
C1560.047 (3)0.034 (2)0.062 (3)0.006 (2)0.006 (3)0.022 (2)
C1570.039 (2)0.050 (3)0.043 (2)−0.009 (2)−0.005 (2)0.019 (2)
Sn20.02770 (14)0.02902 (15)0.02921 (13)0.00306 (11)0.00688 (12)0.01037 (11)
O50.0348 (16)0.0350 (16)0.0269 (14)−0.0008 (13)0.0075 (13)0.0100 (12)
O60.0370 (16)0.0257 (14)0.0291 (14)−0.0022 (12)0.0073 (13)0.0073 (11)
O70.0425 (16)0.0300 (15)0.0313 (14)−0.0011 (12)0.0097 (13)0.0091 (12)
O80.0566 (19)0.0314 (15)0.0297 (15)−0.0025 (13)0.0162 (14)0.0089 (12)
C30.0245 (19)0.027 (2)0.030 (2)0.0034 (16)0.0047 (17)0.0097 (17)
C40.030 (2)0.026 (2)0.032 (2)0.0051 (16)0.0067 (17)0.0089 (16)
C2110.026 (2)0.031 (2)0.0267 (18)0.0046 (17)0.0074 (17)0.0095 (16)
C2120.038 (2)0.038 (2)0.034 (2)0.0018 (19)0.0066 (18)0.0140 (18)
C2130.055 (3)0.029 (2)0.044 (2)0.002 (2)0.000 (2)0.0123 (18)
C2140.050 (3)0.042 (3)0.045 (2)0.017 (2)0.002 (2)0.017 (2)
C2150.038 (2)0.047 (3)0.050 (3)0.001 (2)−0.007 (2)0.014 (2)
C2160.037 (2)0.032 (2)0.041 (2)0.0034 (18)0.0010 (19)0.0113 (18)
C2210.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C2220.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C2230.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C2240.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C2250.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C2260.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C22A0.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C23A0.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C25A0.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C26A0.0361 (12)0.0527 (14)0.0569 (15)0.0060 (10)0.0147 (11)0.0008 (11)
C2320.066 (3)0.031 (2)0.069 (3)0.003 (2)0.027 (3)0.015 (2)
C2330.100 (5)0.032 (2)0.075 (4)0.002 (3)0.016 (3)0.013 (2)
C2310.040 (2)0.032 (2)0.030 (2)0.0033 (18)0.0028 (19)0.0133 (17)
C2340.068 (4)0.055 (3)0.055 (3)−0.025 (3)−0.010 (3)0.032 (3)
C2350.048 (3)0.074 (3)0.047 (3)−0.024 (3)0.000 (2)0.021 (3)
C2360.045 (3)0.053 (3)0.038 (2)−0.009 (2)0.007 (2)0.008 (2)
N20.0278 (17)0.0279 (17)0.0255 (15)0.0013 (13)0.0059 (14)0.0059 (13)
C2410.033 (2)0.043 (2)0.037 (2)0.0008 (18)0.0066 (18)0.0201 (19)
C2420.031 (2)0.030 (2)0.0317 (19)−0.0006 (17)0.0028 (17)0.0140 (16)
C2430.035 (2)0.052 (3)0.033 (2)0.005 (2)0.0061 (18)0.0195 (19)
C2440.035 (2)0.055 (3)0.043 (2)0.008 (2)0.0056 (19)0.017 (2)
C2450.037 (2)0.041 (2)0.045 (2)0.0022 (19)−0.005 (2)0.0127 (19)
C2460.057 (3)0.042 (3)0.028 (2)0.001 (2)−0.007 (2)0.0121 (19)
C2470.045 (3)0.037 (2)0.030 (2)0.006 (2)0.0054 (19)0.0140 (18)
C2510.031 (2)0.052 (3)0.029 (2)0.005 (2)−0.0001 (18)0.0123 (19)
C2520.029 (2)0.045 (3)0.044 (2)0.0101 (18)0.0057 (19)0.021 (2)
C2530.033 (2)0.049 (3)0.047 (2)0.005 (2)0.006 (2)0.024 (2)
C2540.040 (2)0.063 (3)0.053 (3)0.009 (2)0.019 (2)0.029 (2)
C2550.068 (4)0.055 (3)0.082 (4)0.031 (3)0.049 (3)0.025 (3)
C2560.095 (5)0.037 (3)0.129 (6)0.023 (3)0.070 (5)0.035 (3)
C2570.062 (3)0.043 (3)0.088 (4)0.016 (2)0.045 (3)0.029 (3)
Sn30.02328 (13)0.02548 (13)0.02308 (12)0.00236 (11)0.00516 (11)0.00767 (10)
O90.0319 (15)0.0308 (14)0.0229 (13)−0.0046 (12)0.0051 (12)0.0071 (11)
O100.0333 (16)0.0297 (15)0.0263 (14)−0.0007 (12)0.0063 (13)0.0093 (12)
O110.0357 (15)0.0290 (14)0.0250 (13)−0.0041 (12)0.0038 (12)0.0057 (11)
O120.0453 (17)0.0356 (15)0.0239 (14)−0.0067 (13)0.0061 (13)0.0076 (11)
C50.0241 (19)0.027 (2)0.0263 (19)0.0062 (16)0.0049 (17)0.0073 (16)
C60.028 (2)0.027 (2)0.0249 (19)0.0043 (16)0.0064 (17)0.0099 (16)
C3110.0245 (19)0.029 (2)0.0234 (17)0.0073 (16)0.0071 (16)0.0083 (15)
C3120.033 (2)0.033 (2)0.0332 (19)0.0033 (18)0.0021 (18)0.0127 (17)
C3130.043 (2)0.030 (2)0.043 (2)0.0042 (18)0.007 (2)0.0172 (18)
C3140.043 (3)0.039 (2)0.041 (2)0.016 (2)0.008 (2)0.0174 (19)
C3150.031 (2)0.047 (3)0.040 (2)0.006 (2)−0.0011 (19)0.018 (2)
C3160.026 (2)0.035 (2)0.037 (2)0.0014 (17)0.0050 (17)0.0107 (17)
C3210.0238 (18)0.0219 (17)0.0244 (17)0.0082 (14)0.0082 (15)0.0151 (14)
C3220.0274 (19)0.0282 (19)0.039 (2)0.0028 (16)0.0091 (17)0.0134 (16)
C3230.034 (2)0.040 (2)0.053 (3)−0.0002 (19)0.011 (2)0.013 (2)
C3240.032 (2)0.045 (2)0.049 (2)0.0099 (19)0.0146 (19)0.010 (2)
C3250.038 (2)0.033 (2)0.033 (2)0.0072 (18)0.0087 (18)0.0074 (17)
C3260.030 (2)0.032 (2)0.0269 (18)0.0018 (16)0.0000 (16)0.0076 (16)
C3310.026 (2)0.028 (2)0.031 (2)0.0018 (16)0.0056 (17)0.0066 (16)
C3320.036 (2)0.032 (2)0.0304 (19)0.0030 (17)0.0093 (17)0.0091 (16)
C3330.036 (2)0.036 (2)0.035 (2)−0.0007 (18)0.0024 (18)0.0007 (17)
C3340.040 (2)0.028 (2)0.047 (2)−0.0042 (18)0.008 (2)−0.0010 (18)
C3350.061 (3)0.031 (2)0.045 (2)−0.004 (2)0.018 (2)0.0136 (19)
C3360.052 (3)0.030 (2)0.0306 (19)0.0014 (18)0.0085 (18)0.0070 (16)
N30.0249 (16)0.0254 (16)0.0272 (15)0.0026 (13)0.0047 (13)0.0032 (12)
C3410.038 (2)0.059 (3)0.066 (3)0.012 (2)0.021 (2)0.044 (2)
C3420.034 (2)0.031 (2)0.040 (2)0.0090 (17)0.0099 (18)0.0166 (17)
C3430.038 (2)0.072 (3)0.052 (3)0.014 (2)0.013 (2)0.035 (2)
C3440.039 (3)0.073 (3)0.052 (3)0.014 (2)0.009 (2)0.019 (3)
C3450.052 (3)0.043 (3)0.056 (3)0.010 (2)−0.014 (3)0.010 (2)
C3460.068 (4)0.044 (3)0.041 (2)0.010 (3)−0.010 (3)0.014 (2)
C3470.056 (3)0.041 (2)0.037 (2)0.008 (2)0.013 (2)0.0137 (19)
C3510.027 (2)0.043 (2)0.041 (2)0.0062 (19)−0.0026 (19)−0.0010 (19)
C3520.027 (2)0.037 (2)0.0289 (19)0.0054 (17)0.0033 (16)0.0078 (17)
C3530.040 (2)0.054 (3)0.070 (3)0.011 (2)0.015 (2)0.034 (2)
C3540.047 (3)0.084 (4)0.061 (3)0.027 (3)0.027 (3)0.039 (3)
C3550.045 (3)0.065 (3)0.044 (3)0.024 (3)0.000 (2)0.002 (2)
C3560.046 (3)0.032 (2)0.074 (3)0.008 (2)0.009 (3)0.011 (2)
C3570.037 (2)0.048 (3)0.046 (2)0.002 (2)0.004 (2)0.023 (2)
Sn40.02951 (14)0.02650 (14)0.03272 (14)0.00071 (11)0.00739 (12)0.00882 (11)
O130.061 (2)0.0285 (15)0.0313 (15)−0.0081 (15)0.0126 (15)0.0045 (12)
O140.055 (2)0.0302 (16)0.0348 (16)−0.0071 (14)0.0100 (16)0.0087 (13)
O150.067 (2)0.0410 (17)0.0344 (16)−0.0081 (16)0.0116 (15)0.0124 (13)
O160.0494 (18)0.0284 (14)0.0388 (15)−0.0083 (13)0.0076 (14)0.0006 (12)
C70.041 (2)0.030 (2)0.039 (2)−0.0017 (18)0.009 (2)0.0119 (18)
C80.032 (2)0.033 (2)0.037 (2)−0.0011 (18)0.0041 (19)0.0050 (19)
C4110.030 (2)0.033 (2)0.036 (2)0.0035 (18)0.0121 (19)0.0132 (17)
C4120.044 (3)0.037 (2)0.046 (2)0.012 (2)0.013 (2)0.017 (2)
C4130.052 (3)0.039 (3)0.074 (3)0.016 (2)0.021 (3)0.024 (2)
C4140.042 (3)0.052 (3)0.075 (3)0.001 (2)0.006 (3)0.038 (3)
C4150.052 (3)0.049 (3)0.046 (2)−0.009 (2)−0.002 (2)0.027 (2)
C4160.042 (2)0.032 (2)0.043 (2)0.0019 (19)0.006 (2)0.0121 (18)
C4210.0237 (19)0.035 (2)0.0318 (19)0.0000 (17)0.0010 (16)0.0183 (17)
C4220.039 (2)0.039 (2)0.051 (3)−0.003 (2)0.008 (2)0.014 (2)
C4230.034 (2)0.059 (3)0.066 (3)−0.007 (2)0.012 (2)0.026 (3)
C4240.031 (2)0.071 (3)0.054 (3)0.010 (2)0.012 (2)0.034 (3)
C4250.039 (2)0.053 (3)0.034 (2)0.016 (2)0.0063 (19)0.016 (2)
C4260.031 (2)0.041 (2)0.033 (2)0.0041 (18)0.0000 (18)0.0176 (18)
C4310.029 (2)0.031 (2)0.0262 (19)0.0016 (17)0.0080 (17)0.0086 (16)
C4320.035 (2)0.036 (2)0.0297 (19)0.0021 (18)0.0081 (18)0.0110 (17)
C4330.041 (2)0.049 (3)0.032 (2)−0.007 (2)0.0022 (19)0.0097 (19)
C4340.054 (3)0.036 (2)0.038 (2)−0.017 (2)0.011 (2)0.003 (2)
C4350.058 (3)0.032 (2)0.051 (3)0.002 (2)0.011 (2)0.015 (2)
C4360.033 (2)0.033 (2)0.044 (2)−0.0019 (18)0.0044 (19)0.0119 (18)
N40.0275 (17)0.0308 (17)0.0243 (15)0.0018 (13)0.0042 (14)0.0061 (13)
C4410.029 (2)0.043 (2)0.0294 (19)0.0025 (17)−0.0028 (17)0.0073 (17)
C4420.028 (2)0.037 (2)0.035 (2)0.0001 (17)−0.0006 (18)0.0105 (18)
C4430.048 (3)0.043 (2)0.053 (3)0.004 (2)0.016 (2)0.021 (2)
C4440.067 (3)0.066 (3)0.057 (3)0.013 (3)0.035 (3)0.022 (3)
C4450.059 (3)0.049 (3)0.062 (3)0.006 (3)0.015 (3)0.000 (3)
C4460.044 (3)0.046 (3)0.077 (4)0.003 (2)0.010 (3)0.016 (3)
C4470.038 (3)0.046 (3)0.049 (3)0.006 (2)0.003 (2)0.016 (2)
C4510.039 (2)0.058 (3)0.040 (2)−0.003 (2)0.009 (2)0.029 (2)
C4520.038 (2)0.035 (2)0.034 (2)0.0000 (18)0.0043 (19)0.0183 (18)
C4530.041 (2)0.073 (3)0.030 (2)0.001 (2)0.0030 (19)0.015 (2)
C4540.035 (2)0.073 (3)0.040 (2)0.011 (2)0.010 (2)0.016 (2)
C4550.036 (2)0.051 (3)0.047 (2)0.010 (2)0.002 (2)0.024 (2)
C4560.047 (3)0.048 (2)0.036 (2)0.007 (2)−0.008 (2)0.0165 (19)
C4570.046 (2)0.039 (2)0.0310 (19)0.0075 (18)0.0058 (18)0.0097 (17)
Geometric parameters (Å, º) top
Sn1—O12.124 (3)C255—C2561.365 (8)
Sn1—C1212.131 (4)C255—H2550.9500
Sn1—C1112.156 (4)C256—C2571.384 (8)
Sn1—C1312.160 (4)C256—H2560.9500
Sn1—O22.306 (3)C257—H2570.9500
O1—C11.290 (5)Sn3—O92.104 (3)
O2—C21.260 (5)Sn3—C3112.142 (4)
O3—C11.228 (5)Sn3—C3212.142 (4)
O4—C21.248 (5)Sn3—C3312.185 (4)
C1—C21.528 (6)Sn3—O102.355 (3)
C111—C1121.384 (6)O9—C61.295 (5)
C111—C1161.387 (5)O10—C51.259 (5)
C112—C1131.383 (7)O11—C51.242 (4)
C112—H1120.9500O12—C61.216 (5)
C113—C1141.374 (7)C5—C61.554 (6)
C113—H1130.9500C311—C3161.392 (5)
C114—C1151.366 (7)C311—C3121.402 (5)
C114—H1140.9500C312—C3131.399 (6)
C115—C1161.383 (6)C312—H3120.9500
C115—H1150.9500C313—C3141.383 (6)
C116—H1160.9500C313—H3130.9500
C121—C1221.385 (6)C314—C3151.386 (6)
C121—C1261.399 (6)C314—H3140.9500
C122—C1231.396 (6)C315—C3161.371 (6)
C122—H1220.9500C315—H3150.9500
C123—C1241.379 (6)C316—H3160.9500
C123—H1230.9500C321—C3221.395 (5)
C124—C1251.383 (6)C321—C3261.416 (5)
C124—H1240.9500C322—C3231.396 (6)
C125—C1261.395 (6)C322—H3220.9500
C125—H1250.9500C323—C3241.390 (6)
C126—H1260.9500C323—H3230.9500
C131—C1361.401 (6)C324—C3251.381 (6)
C131—C1321.402 (7)C324—H3240.9500
C132—C1331.373 (6)C325—C3261.380 (6)
C132—H1320.9500C325—H3250.9500
C133—C1341.417 (8)C326—H3260.9500
C133—H1330.9500C331—C3361.396 (6)
C134—C1351.371 (8)C331—C3321.407 (5)
C134—H1340.9500C332—C3331.390 (5)
C135—C1361.394 (7)C332—H3320.9500
C135—H1350.9500C333—C3341.381 (6)
C136—H1360.9500C333—H3330.9500
N1—C1411.486 (5)C334—C3351.398 (6)
N1—C1511.510 (5)C334—H3340.9500
N1—H1A0.9200C335—C3361.372 (6)
N1—H1B0.9200C335—H3350.9500
C141—C1421.504 (6)C336—H3360.9500
C141—H14A0.9900N3—C3411.474 (5)
C141—H14B0.9900N3—C3511.499 (5)
C142—C1431.380 (6)N3—H3A0.9200
C142—C1471.403 (6)N3—H3B0.9200
C143—C1441.399 (6)C341—C3421.500 (6)
C143—H1430.9500C341—H34A0.9900
C144—C1451.374 (6)C341—H34B0.9900
C144—H1440.9500C342—C3431.379 (6)
C145—C1461.362 (6)C342—C3471.388 (6)
C145—H1450.9500C343—C3441.393 (6)
C146—C1471.399 (6)C343—H3430.9500
C146—H1460.9500C344—C3451.373 (7)
C147—H1470.9500C344—H3440.9500
C151—C1521.503 (6)C345—C3461.376 (8)
C151—H15A0.9900C345—H3450.9500
C151—H15B0.9900C346—C3471.387 (7)
C152—C1531.387 (6)C346—H3460.9500
C152—C1571.400 (6)C347—H3470.9500
C153—C1541.384 (6)C351—C3521.522 (6)
C153—H1530.9500C351—H35A0.9900
C154—C1551.407 (7)C351—H35B0.9900
C154—H1540.9500C352—C3531.370 (6)
C155—C1561.364 (7)C352—C3571.375 (6)
C155—H1550.9500C353—C3541.394 (7)
C156—C1571.417 (7)C353—H3530.9500
C156—H1560.9500C354—C3551.393 (8)
C157—H1570.9500C354—H3540.9500
Sn2—O62.116 (3)C355—C3561.368 (7)
Sn2—C2212.131 (5)C355—H3550.9500
Sn2—C2112.147 (4)C356—C3571.373 (7)
Sn2—C2312.167 (4)C356—H3560.9500
Sn2—O52.317 (3)C357—H3570.9500
O5—C31.262 (5)Sn4—O132.117 (3)
O6—C41.305 (5)Sn4—C4212.133 (4)
O7—C31.238 (5)Sn4—C4112.140 (4)
O8—C41.230 (5)Sn4—C4312.168 (4)
C3—C41.538 (5)Sn4—O142.289 (3)
C211—C2121.383 (6)O13—C71.290 (5)
C211—C2161.393 (5)O14—C81.256 (5)
C212—C2131.386 (6)O15—C71.226 (5)
C212—H2120.9500O16—C81.249 (5)
C213—C2141.360 (6)C7—C81.552 (6)
C213—H2130.9500C411—C4161.382 (6)
C214—C2151.381 (6)C411—C4121.407 (6)
C214—H2140.9500C412—C4131.378 (7)
C215—C2161.372 (6)C412—H4120.9500
C215—H2150.9500C413—C4141.365 (7)
C216—H2160.9500C413—H4130.9500
C221—C22A1.339 (13)C414—C4151.401 (8)
C221—C2261.364 (8)C414—H4140.9500
C221—C2221.392 (8)C415—C4161.390 (6)
C221—C26A1.411 (13)C415—H4150.9500
C222—C2231.389 (9)C416—H4160.9500
C222—H2220.9500C421—C4261.382 (6)
C223—C2241.423 (8)C421—C4221.413 (5)
C223—H2230.9500C422—C4231.383 (7)
C224—C2251.283 (8)C422—H4220.9500
C224—C25A1.341 (13)C423—C4241.394 (7)
C224—C23A1.419 (13)C423—H4230.9500
C224—H2240.9500C424—C4251.367 (7)
C225—C2261.392 (9)C424—H4240.9500
C225—H2250.9500C425—C4261.398 (6)
C226—H2260.9500C425—H4250.9500
C22A—C23A1.377 (15)C426—H4260.9500
C22A—H22A0.9500C431—C4361.380 (6)
C23A—H23A0.9500C431—C4321.400 (6)
C25A—C26A1.410 (14)C432—C4331.384 (6)
C25A—H25A0.9500C432—H4320.9500
C26A—H26A0.9500C433—C4341.386 (7)
C232—C2311.383 (6)C433—H4330.9500
C232—C2331.412 (7)C434—C4351.375 (7)
C232—H2320.9500C434—H4340.9500
C233—C2341.339 (8)C435—C4361.385 (6)
C233—H2330.9500C435—H4350.9500
C231—C2361.396 (6)C436—H4360.9500
C234—C2351.371 (7)N4—C4511.475 (5)
C234—H2340.9500N4—C4411.515 (5)
C235—C2361.379 (6)N4—H4A0.9200
C235—H2350.9500N4—H4B0.9200
C236—H2360.9500C441—C4421.499 (6)
N2—C2411.493 (5)C441—H44A0.9900
N2—C2511.508 (5)C441—H44B0.9900
N2—H2A0.9200C442—C4431.366 (6)
N2—H2B0.9200C442—C4471.392 (6)
C241—C2421.518 (6)C443—C4441.397 (6)
C241—H24A0.9900C443—H4430.9500
C241—H24B0.9900C444—C4451.350 (7)
C242—C2471.371 (5)C444—H4440.9500
C242—C2431.383 (6)C445—C4461.393 (8)
C243—C2441.372 (6)C445—H4450.9500
C243—H2430.9500C446—C4471.369 (7)
C244—C2451.382 (6)C446—H4460.9500
C244—H2440.9500C447—H4470.9500
C245—C2461.374 (7)C451—C4521.501 (6)
C245—H2450.9500C451—H45A0.9900
C246—C2471.383 (6)C451—H45B0.9900
C246—H2460.9500C452—C4531.384 (6)
C247—H2470.9500C452—C4571.388 (6)
C251—C2521.499 (6)C453—C4541.402 (6)
C251—H25B0.9900C453—H4530.9500
C251—H25C0.9900C454—C4551.377 (6)
C252—C2571.359 (6)C454—H4540.9500
C252—C2531.393 (6)C455—C4561.382 (6)
C253—C2541.383 (6)C455—H4550.9500
C253—H2530.9500C456—C4571.382 (6)
C254—C2551.362 (7)C456—H4560.9500
C254—H2540.9500C457—H4570.9500
O1—Sn1—C121114.33 (14)C252—C253—H253119.7
O1—Sn1—C111126.26 (15)C255—C254—C253119.5 (5)
C121—Sn1—C111113.62 (16)C255—C254—H254120.3
O1—Sn1—C13183.18 (14)C253—C254—H254120.3
C121—Sn1—C131105.98 (16)C254—C255—C256120.3 (5)
C111—Sn1—C131105.50 (16)C254—C255—H255119.9
O1—Sn1—O272.26 (10)C256—C255—H255119.9
C121—Sn1—O290.45 (13)C255—C256—C257120.3 (5)
C111—Sn1—O284.60 (13)C255—C256—H256119.9
C131—Sn1—O2154.56 (13)C257—C256—H256119.9
C1—O1—Sn1121.4 (3)C252—C257—C256120.6 (5)
C2—O2—Sn1115.8 (3)C252—C257—H257119.7
O3—C1—O1123.9 (4)C256—C257—H257119.7
O3—C1—C2121.1 (3)O9—Sn3—C311118.60 (13)
O1—C1—C2114.9 (3)O9—Sn3—C321116.83 (12)
O4—C2—O2127.1 (4)C311—Sn3—C321117.37 (14)
O4—C2—C1117.4 (4)O9—Sn3—C33187.55 (13)
O2—C2—C1115.6 (3)C311—Sn3—C331104.59 (15)
C112—C111—C116118.2 (4)C321—Sn3—C331104.57 (15)
C112—C111—Sn1124.1 (3)O9—Sn3—O1072.12 (10)
C116—C111—Sn1117.7 (3)C311—Sn3—O1085.51 (12)
C113—C112—C111120.7 (4)C321—Sn3—O1085.53 (12)
C113—C112—H112119.7C331—Sn3—O10159.67 (12)
C111—C112—H112119.7C6—O9—Sn3122.6 (2)
C114—C113—C112119.8 (5)C5—O10—Sn3115.2 (2)
C114—C113—H113120.1O11—C5—O10127.5 (4)
C112—C113—H113120.1O11—C5—C6117.7 (3)
C115—C114—C113120.8 (4)O10—C5—C6114.8 (3)
C115—C114—H114119.6O12—C6—O9125.1 (4)
C113—C114—H114119.6O12—C6—C5119.8 (3)
C114—C115—C116119.2 (4)O9—C6—C5115.1 (3)
C114—C115—H115120.4C316—C311—C312117.6 (4)
C116—C115—H115120.4C316—C311—Sn3119.7 (3)
C115—C116—C111121.4 (4)C312—C311—Sn3122.4 (3)
C115—C116—H116119.3C313—C312—C311120.8 (4)
C111—C116—H116119.3C313—C312—H312119.6
C122—C121—C126118.3 (4)C311—C312—H312119.6
C122—C121—Sn1122.8 (3)C314—C313—C312119.7 (4)
C126—C121—Sn1118.8 (3)C314—C313—H313120.1
C121—C122—C123120.5 (4)C312—C313—H313120.1
C121—C122—H122119.7C313—C314—C315119.8 (4)
C123—C122—H122119.7C313—C314—H314120.1
C124—C123—C122120.6 (4)C315—C314—H314120.1
C124—C123—H123119.7C316—C315—C314120.3 (4)
C122—C123—H123119.7C316—C315—H315119.9
C123—C124—C125119.8 (4)C314—C315—H315119.9
C123—C124—H124120.1C315—C316—C311121.8 (4)
C125—C124—H124120.1C315—C316—H316119.1
C124—C125—C126119.6 (4)C311—C316—H316119.1
C124—C125—H125120.2C322—C321—C326118.7 (4)
C126—C125—H125120.2C322—C321—Sn3123.6 (3)
C125—C126—C121121.2 (4)C326—C321—Sn3117.5 (3)
C125—C126—H126119.4C321—C322—C323120.6 (4)
C121—C126—H126119.4C321—C322—H322119.7
C136—C131—C132117.5 (4)C323—C322—H322119.7
C136—C131—Sn1122.2 (4)C324—C323—C322119.7 (4)
C132—C131—Sn1120.1 (3)C324—C323—H323120.2
C133—C132—C131122.5 (4)C322—C323—H323120.2
C133—C132—H132118.7C325—C324—C323120.3 (4)
C131—C132—H132118.7C325—C324—H324119.8
C132—C133—C134118.9 (5)C323—C324—H324119.8
C132—C133—H133120.6C326—C325—C324120.6 (4)
C134—C133—H133120.6C326—C325—H325119.7
C135—C134—C133119.5 (5)C324—C325—H325119.7
C135—C134—H134120.2C325—C326—C321120.2 (4)
C133—C134—H134120.2C325—C326—H326119.9
C134—C135—C136121.0 (5)C321—C326—H326119.9
C134—C135—H135119.5C336—C331—C332117.2 (3)
C136—C135—H135119.5C336—C331—Sn3122.8 (3)
C135—C136—C131120.5 (5)C332—C331—Sn3119.9 (3)
C135—C136—H136119.7C333—C332—C331121.3 (4)
C131—C136—H136119.7C333—C332—H332119.3
C141—N1—C151114.4 (3)C331—C332—H332119.3
C141—N1—H1A108.7C334—C333—C332119.7 (4)
C151—N1—H1A108.7C334—C333—H333120.2
C141—N1—H1B108.7C332—C333—H333120.2
C151—N1—H1B108.7C333—C334—C335119.9 (4)
H1A—N1—H1B107.6C333—C334—H334120.0
N1—C141—C142110.7 (3)C335—C334—H334120.0
N1—C141—H14A109.5C336—C335—C334119.8 (4)
C142—C141—H14A109.5C336—C335—H335120.1
N1—C141—H14B109.5C334—C335—H335120.1
C142—C141—H14B109.5C335—C336—C331122.0 (4)
H14A—C141—H14B108.1C335—C336—H336119.0
C143—C142—C147118.7 (4)C331—C336—H336119.0
C143—C142—C141121.2 (4)C341—N3—C351113.5 (3)
C147—C142—C141120.1 (4)C341—N3—H3A108.9
C142—C143—C144121.1 (4)C351—N3—H3A108.9
C142—C143—H143119.4C341—N3—H3B108.9
C144—C143—H143119.4C351—N3—H3B108.9
C145—C144—C143119.4 (4)H3A—N3—H3B107.7
C145—C144—H144120.3N3—C341—C342113.4 (3)
C143—C144—H144120.3N3—C341—H34A108.9
C146—C145—C144120.6 (4)C342—C341—H34A108.9
C146—C145—H145119.7N3—C341—H34B108.9
C144—C145—H145119.7C342—C341—H34B108.9
C145—C146—C147120.7 (4)H34A—C341—H34B107.7
C145—C146—H146119.6C343—C342—C347119.0 (4)
C147—C146—H146119.6C343—C342—C341123.6 (4)
C146—C147—C142119.5 (4)C347—C342—C341117.3 (4)
C146—C147—H147120.3C342—C343—C344120.3 (4)
C142—C147—H147120.3C342—C343—H343119.8
C152—C151—N1111.1 (3)C344—C343—H343119.8
C152—C151—H15A109.4C345—C344—C343120.4 (5)
N1—C151—H15A109.4C345—C344—H344119.8
C152—C151—H15B109.4C343—C344—H344119.8
N1—C151—H15B109.4C344—C345—C346119.4 (5)
H15A—C151—H15B108.0C344—C345—H345120.3
C153—C152—C157118.5 (4)C346—C345—H345120.3
C153—C152—C151121.7 (4)C345—C346—C347120.7 (5)
C157—C152—C151119.8 (4)C345—C346—H346119.7
C154—C153—C152120.9 (4)C347—C346—H346119.7
C154—C153—H153119.5C346—C347—C342120.2 (5)
C152—C153—H153119.5C346—C347—H347119.9
C153—C154—C155119.7 (4)C342—C347—H347119.9
C153—C154—H154120.2N3—C351—C352113.1 (3)
C155—C154—H154120.2N3—C351—H35A109.0
C156—C155—C154121.1 (5)C352—C351—H35A109.0
C156—C155—H155119.4N3—C351—H35B109.0
C154—C155—H155119.4C352—C351—H35B109.0
C155—C156—C157118.5 (5)H35A—C351—H35B107.8
C155—C156—H156120.8C353—C352—C357118.9 (4)
C157—C156—H156120.8C353—C352—C351119.6 (4)
C152—C157—C156121.3 (4)C357—C352—C351121.5 (4)
C152—C157—H157119.4C352—C353—C354120.0 (5)
C156—C157—H157119.4C352—C353—H353120.0
O6—Sn2—C221121.57 (17)C354—C353—H353120.0
O6—Sn2—C211116.99 (13)C355—C354—C353120.2 (5)
C221—Sn2—C211115.19 (19)C355—C354—H354119.9
O6—Sn2—C23184.98 (13)C353—C354—H354119.9
C221—Sn2—C231107.13 (19)C356—C355—C354119.3 (5)
C211—Sn2—C231103.03 (15)C356—C355—H355120.3
O6—Sn2—O572.71 (10)C354—C355—H355120.3
C221—Sn2—O586.49 (15)C355—C356—C357119.7 (5)
C211—Sn2—O586.21 (13)C355—C356—H356120.1
C231—Sn2—O5157.64 (13)C357—C356—H356120.1
C3—O5—Sn2115.9 (3)C356—C357—C352121.9 (5)
C4—O6—Sn2120.8 (2)C356—C357—H357119.1
O7—C3—O5127.2 (4)C352—C357—H357119.1
O7—C3—C4117.8 (3)O13—Sn4—C421115.39 (14)
O5—C3—C4114.9 (3)O13—Sn4—C411127.11 (15)
O8—C4—O6124.0 (4)C421—Sn4—C411112.96 (15)
O8—C4—C3120.5 (3)O13—Sn4—C43181.50 (13)
O6—C4—C3115.6 (3)C421—Sn4—C431107.16 (15)
C212—C211—C216118.2 (4)C411—Sn4—C431103.67 (16)
C212—C211—Sn2124.0 (3)O13—Sn4—O1472.69 (11)
C216—C211—Sn2117.8 (3)C421—Sn4—O1491.89 (14)
C211—C212—C213119.9 (4)C411—Sn4—O1485.73 (14)
C211—C212—H212120.1C431—Sn4—O14152.79 (13)
C213—C212—H212120.1C7—O13—Sn4121.4 (3)
C214—C213—C212121.3 (4)C8—O14—Sn4116.1 (3)
C214—C213—H213119.4O15—C7—O13125.5 (4)
C212—C213—H213119.4O15—C7—C8120.2 (4)
C213—C214—C215119.5 (4)O13—C7—C8114.3 (4)
C213—C214—H214120.2O16—C8—O14127.6 (4)
C215—C214—H214120.2O16—C8—C7117.3 (4)
C216—C215—C214119.8 (4)O14—C8—C7115.1 (4)
C216—C215—H215120.1C416—C411—C412118.6 (4)
C214—C215—H215120.1C416—C411—Sn4115.9 (3)
C215—C216—C211121.3 (4)C412—C411—Sn4125.4 (3)
C215—C216—H216119.3C413—C412—C411119.4 (4)
C211—C216—H216119.3C413—C412—H412120.3
C22A—C221—C22694.4 (8)C411—C412—H412120.3
C22A—C221—C22250.2 (7)C414—C413—C412122.0 (5)
C226—C221—C222116.2 (5)C414—C413—H413119.0
C22A—C221—C26A115.5 (9)C412—C413—H413119.0
C226—C221—C26A36.2 (7)C413—C414—C415119.4 (5)
C222—C221—C26A106.2 (7)C413—C414—H414120.3
C22A—C221—Sn2117.7 (7)C415—C414—H414120.3
C226—C221—Sn2118.9 (4)C416—C415—C414119.1 (4)
C222—C221—Sn2124.4 (4)C416—C415—H415120.5
C26A—C221—Sn2122.2 (6)C414—C415—H415120.5
C223—C222—C221121.9 (6)C411—C416—C415121.5 (4)
C223—C222—H222119.0C411—C416—H416119.3
C221—C222—H222119.0C415—C416—H416119.3
C222—C223—C224117.8 (6)C426—C421—C422118.5 (4)
C222—C223—H223121.1C426—C421—Sn4118.8 (3)
C224—C223—H223121.1C422—C421—Sn4121.9 (3)
C225—C224—C25A30.9 (8)C423—C422—C421120.1 (4)
C225—C224—C23A94.9 (7)C423—C422—H422120.0
C25A—C224—C23A115.4 (9)C421—C422—H422120.0
C225—C224—C223120.3 (6)C422—C423—C424120.2 (4)
C25A—C224—C223113.5 (8)C422—C423—H423119.9
C23A—C224—C22352.2 (7)C424—C423—H423119.9
C225—C224—H224119.8C425—C424—C423120.3 (4)
C25A—C224—H224117.5C425—C424—H424119.9
C23A—C224—H224122.0C423—C424—H424119.9
C223—C224—H224119.8C424—C425—C426119.8 (4)
C224—C225—C226121.5 (6)C424—C425—H425120.1
C224—C225—H225119.2C426—C425—H425120.1
C226—C225—H225119.2C421—C426—C425121.1 (4)
C221—C226—C225122.1 (6)C421—C426—H426119.5
C221—C226—H226119.0C425—C426—H426119.5
C225—C226—H226119.0C436—C431—C432117.6 (4)
C221—C22A—C23A121.6 (12)C436—C431—Sn4119.8 (3)
C221—C22A—H22A119.2C432—C431—Sn4122.1 (3)
C23A—C22A—H22A119.2C433—C432—C431121.4 (4)
C22A—C23A—C224119.9 (12)C433—C432—H432119.3
C22A—C23A—H23A120.1C431—C432—H432119.3
C224—C23A—H23A120.1C432—C433—C434119.3 (4)
C224—C25A—C26A117.8 (11)C432—C433—H433120.4
C224—C25A—H25A121.1C434—C433—H433120.4
C26A—C25A—H25A121.1C435—C434—C433120.2 (4)
C25A—C26A—C221121.8 (12)C435—C434—H434119.9
C25A—C26A—H26A119.1C433—C434—H434119.9
C221—C26A—H26A119.1C434—C435—C436119.9 (4)
C231—C232—C233120.8 (5)C434—C435—H435120.1
C231—C232—H232119.6C436—C435—H435120.1
C233—C232—H232119.6C431—C436—C435121.6 (4)
C234—C233—C232121.3 (5)C431—C436—H436119.2
C234—C233—H233119.4C435—C436—H436119.2
C232—C233—H233119.4C451—N4—C441114.6 (3)
C232—C231—C236115.9 (4)C451—N4—H4A108.6
C232—C231—Sn2124.8 (3)C441—N4—H4A108.6
C236—C231—Sn2119.3 (3)C451—N4—H4B108.6
C233—C234—C235119.3 (5)C441—N4—H4B108.6
C233—C234—H234120.3H4A—N4—H4B107.6
C235—C234—H234120.3C442—C441—N4112.8 (3)
C234—C235—C236120.0 (5)C442—C441—H44A109.0
C234—C235—H235120.0N4—C441—H44A109.0
C236—C235—H235120.0C442—C441—H44B109.0
C235—C236—C231122.6 (4)N4—C441—H44B109.0
C235—C236—H236118.7H44A—C441—H44B107.8
C231—C236—H236118.7C443—C442—C447118.7 (4)
C241—N2—C251114.7 (3)C443—C442—C441121.9 (4)
C241—N2—H2A108.6C447—C442—C441119.4 (4)
C251—N2—H2A108.6C442—C443—C444120.8 (4)
C241—N2—H2B108.6C442—C443—H443119.6
C251—N2—H2B108.6C444—C443—H443119.6
H2A—N2—H2B107.6C445—C444—C443119.7 (5)
N2—C241—C242113.0 (3)C445—C444—H444120.2
N2—C241—H24A109.0C443—C444—H444120.2
C242—C241—H24A109.0C444—C445—C446120.5 (5)
N2—C241—H24B109.0C444—C445—H445119.7
C242—C241—H24B109.0C446—C445—H445119.7
H24A—C241—H24B107.8C447—C446—C445119.4 (5)
C247—C242—C243119.2 (4)C447—C446—H446120.3
C247—C242—C241118.1 (4)C445—C446—H446120.3
C243—C242—C241122.6 (3)C446—C447—C442120.8 (5)
C244—C243—C242120.5 (4)C446—C447—H447119.6
C244—C243—H243119.8C442—C447—H447119.6
C242—C243—H243119.8N4—C451—C452112.9 (3)
C243—C244—C245120.4 (4)N4—C451—H45A109.0
C243—C244—H244119.8C452—C451—H45A109.0
C245—C244—H244119.8N4—C451—H45B109.0
C246—C245—C244119.0 (4)C452—C451—H45B109.0
C246—C245—H245120.5H45A—C451—H45B107.8
C244—C245—H245120.5C453—C452—C457118.9 (4)
C245—C246—C247120.6 (4)C453—C452—C451122.3 (4)
C245—C246—H246119.7C457—C452—C451118.5 (4)
C247—C246—H246119.7C452—C453—C454120.5 (4)
C242—C247—C246120.2 (4)C452—C453—H453119.7
C242—C247—H247119.9C454—C453—H453119.7
C246—C247—H247119.9C455—C454—C453119.9 (4)
C252—C251—N2113.1 (3)C455—C454—H454120.0
C252—C251—H25B108.9C453—C454—H454120.0
N2—C251—H25B108.9C454—C455—C456119.5 (4)
C252—C251—H25C108.9C454—C455—H455120.3
N2—C251—H25C108.9C456—C455—H455120.3
H25B—C251—H25C107.8C455—C456—C457120.8 (4)
C257—C252—C253118.6 (4)C455—C456—H456119.6
C257—C252—C251119.8 (4)C457—C456—H456119.6
C253—C252—C251121.5 (4)C456—C457—C452120.3 (4)
C254—C253—C252120.7 (4)C456—C457—H457119.8
C254—C253—H253119.7C452—C457—H457119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O40.921.942.847 (4)171
N1—H1B···O150.922.262.902 (4)126
N1—H1B···O160.921.982.805 (4)148
N2—H2A···O70.921.922.795 (4)159
N2—H2B···O110.922.052.857 (4)146
N2—H2B···O120.922.272.925 (4)128
N3—H3A···O70.922.212.951 (4)137
N3—H3A···O80.922.082.813 (4)136
N3—H3B···O110.921.912.816 (4)169
N4—H4A···O30.922.152.843 (4)131
N4—H4A···O40.922.102.843 (4)137
N4—H4B···O160.921.842.755 (4)177

Experimental details

Crystal data
Chemical formula(C14H16N)[Sn(C6H5)3(C2O2)]
Mr636.31
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)9.8575 (2), 16.8894 (3), 18.9812 (4)
α, β, γ (°)110.444 (1), 96.082 (1), 93.384 (1)
V (Å3)2928.73 (10)
Z4
Radiation typeMo Kα
µ (mm−1)0.91
Crystal size (mm)0.40 × 0.20 × 0.10
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.712, 0.914
No. of measured, independent and
observed [I > 2σ(I)] reflections		56750, 22478, 20136
Rint0.038
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.070, 1.06
No. of reflections22474
No. of parameters1424
No. of restraints15
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.61, −0.86
Absolute structureFlack (1983), with 10508 Fridel pairs
Absolute structure parameter0.438 (10)

Computer programs: COLLECT (Nonius, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Sn1—O12.124 (3)Sn3—O92.104 (3)
Sn1—C1212.131 (4)Sn3—C3112.142 (4)
Sn1—C1112.156 (4)Sn3—C3212.142 (4)
Sn1—C1312.160 (4)Sn3—C3312.185 (4)
Sn1—O22.306 (3)Sn3—O102.355 (3)
Sn2—O62.116 (3)Sn4—O132.117 (3)
Sn2—C2212.131 (5)Sn4—C4212.133 (4)
Sn2—C2112.147 (4)Sn4—C4112.140 (4)
Sn2—C2312.167 (4)Sn4—C4312.168 (4)
Sn2—O52.317 (3)Sn4—O142.289 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O40.921.942.847 (4)170.8
N1—H1B···O150.922.262.902 (4)126.1
N1—H1B···O160.921.982.805 (4)147.9
N2—H2A···O70.921.922.795 (4)158.9
N2—H2B···O110.922.052.857 (4)146.0
N2—H2B···O120.922.272.925 (4)127.6
N3—H3A···O70.922.212.951 (4)136.6
N3—H3A···O80.922.082.813 (4)136.1
N3—H3B···O110.921.912.816 (4)169.1
N4—H4A···O30.922.152.843 (4)131.0
N4—H4A···O40.922.102.843 (4)137.2
N4—H4B···O160.921.842.755 (4)176.9
 

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBlessing, R. H. (1997). J. Appl. Cryst. 30, 421–426.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationEvans, J. C. & Karpel, S. (1985). In Organotin Compounds in Modern Technology. Amsterdam: Elsevier.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationNg, S. W. & Hook, J. M. (1999). Acta Cryst. C55, 310–312.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationNg, S. W. & Kumar Das, V. G. (1995). Acta Cryst. C51, 2489–2491.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationNg, S. W. & Rae, A. D. (2000). Z. Kristallogr. 215, 199–204.  Web of Science CSD CrossRef CAS Google Scholar
 First citationNonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 6| June 2012| Pages m854-m855
doi:10.1107/S1600536812021125
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