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catena-Poly­[di­cyclo­hexyl­ammonium [tri­butyl­tin-[mu]-(4-oxo-4H-pyran-2,6-di­carboxyl­ato-O2:O6)]], (C12­H24N)­[Sn(C7­H2­O6)(C4H9)3], consists of 4-oxo-4H-pyran-2,6-di­carboxyl­ato groups that axially link adjacent tri­butyl­tin units into a linear polyanionic chain. The ammonium counter-ions surround the chain, and each cation forms a pair of hydrogen bonds to the double-bond carbonyl O atoms of the same dianionic group. The chain propagates in a zigzag manner along the c axis of the monoclinic cell. In catena-poly­[methyl­(phenyl)­ammonium [tri­butyl­tin-[mu]-(pyridine-2,6-di­carboxyl­ato-O2:O6)]], (C7H10N)­[Sn(C7H3NO4)­(C4H9)3], the pyridine-2,6-di­carboxyl­ato groups also link the tri­butyl­tin groups into a chain, but the hydrogen-bonded chain propagates linearly on the ac face of the monoclinic cell.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008106/sk1382sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008106/sk1382Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008106/sk1382IIsup3.hkl
Contains datablock II

CCDC references: 150325; 150326

Comment top

Among the triorganotin derivatives of polycarboxylic acids, the ammonium triorganotin dicarboxylates represent a class of stannates whose biological properties are expected to be improved compared with those of neutral triorganotin monocarboxylates or bis(triorganotin) dicarboxylates because of the potentially greater degree of aqueous solubility. Dicyclohexylammonium tributyltin pyridine-2,6-dicarboxylate exists as a linear hydrogen-bonded polyanionic chain motif; the ammonium counterions surround the chain and they interact with the double-bond carbonyl oxygen atoms through hydrogen bonds [N···O = 2.75, 2.79 Å] (Ng, Kumar Das & Tiekink et al., 1991). The replacement of the pyridyl unit by the 4-oxo-4H-pyranyl entity results in the formation of a similar hydrogen-bonded architecture for dicyclohexylammonium 4-oxo-4H-pyran-2,6-dicarboxylatotributylstannate, (I), which crystallizes as two symmetry-independent hydrogen-bonded chains. These are approximately related by (0.5 + x, y, 0.45 − z), such a relationship suggesting the possibility of a stacking fault. The tin atoms show trans-C3SnO2 trigonal bipyramidal coordination [chain a: Sn—O = 2.285 (4), 2.292 (4) Å, O—Sn—O = 174.3 (2)°; chain b: Sn—O = 2.286 (5), 2.292 (5) Å, O—Sn—O = 176.0 (2)°]; the negatively-charged carboxyl oxygen atoms of the dicarboxylato dianion binds to two adjacent tributyltin cations. The tin-oxygen bond distances are longer than covalent tin-oxygen bonds but shorter than dative tin-oxygen bonds found in most triorganotin carboxylates (Tiekink, 1991, 1994). The bond distances are somewhat longer than those [Sn—O = 2.26 (1), 2.31 (1) Å] found in poly(dicyclohexylammonium 2,6-pyridinedicarboxylatotributylstannate) (Ng, Kumar Das & Tiekink et al., 1991) and that [Sn—O = 2.214 (2) Å] found in poly(dicyclohexylammonium succinatotriphenylstannate) (Ng, Kumar Das, Xiao et al., 1991); in (I), the tin atom lies on a special position so that the two tin-oxygen bonds are equivalent. \sch

The connectivity between the dianionic and cationic groups leads to the formation of a polyanionic zigzag chain structure. The sec-ammonium cations surround the chain, and each cation forms a pair of hydrogen bonds [chain a: N···O = 2.785 (7), 2.788 (7) Å; chain b: N···O = 2.765 (7), 2.786 (8) Å]. The ketonic oxygen atom of the 4-oxo-4H-pyran moiety is not involved in hydrogen bonding.

Whereas poly(2,6-pyridinedicarboxylatotributylstannate) adopts a zigzag chain motif in the dicyclohexylammonium derivative (Ng, Kumar Das & Tiekink et al., 1991), the polyanion in methylphenylammonium pyridine-2,6-dicarboxylatotributylstannate, (II), adopts a linear arrangement that is neither zigzag or helical as the chain propagates on the a-c face of the monoclinic cell. The repeat distance of (II) is half the a-c diagonal (a/c = 11.10 Å); this distance is nearly identical to that (c/2 = 11.06 Å) of the dicyclohexylammonium derivative. The similarity of the two repeat distances suggests that the nature of the ammonium counterion governs packing. However, the packing of both compounds appears to be inefficient, as noted from the accessible voids. In (II), there are two such voids of 37.6 Å3 in the unit cell. The hydrogen bonds in (II) [N···O = 2.732 (5), 2.763 (4) Å] are much shorter than that [N···O = 2.904 (3) Å] found in the methylphenylammonium hydrogen 2,6-pyridinedicarboxylate (Ng & Turnbull, 1998) reactant.

Experimental top

Dicyclohexylamine (1.81 g, 10 mmol) and 4-oxo-4H-pyran-2,6-dicarboxylic (chelidonic) acid (1.84 g, 10 mol) were heated in a small volume of ethanol until the acid dissolved completely. The addition of bis(tributyltin) oxide (2.98 g, 5 mmol) gave an immediate precipitate. More ethanol was added to dissolve the solid, and slow evaporation of the filtered solution led to yellow blocks of (I). The solid-state 119Sn NMR spectrum consists of three signals (4:3:1 intensity ratio) at −55, −60 and −64 p.p.m. relative to tetramethyltin. A similar reaction with N-methylaniline, 2,6-pyridinedicarboxylic acid and bis(tributyltin) oxide gave (II) as long plates.

Refinement top

For (I), the 1,2- and 1,3-related carbon-carbon distances in the butyl chains and cyclohexyl rings were restrained by DFIX 1.54±0.01 and DFIX 2.52±0.02 Å; temperature factor restraints (SIMU 0.02) were imposed on the six butyl groups. Additionally, the temperature factors were restrained so that the ellipsoids would not be too elongated by an ISOR 0.02 command in SHELXL97 (Sheldrick, 1997). The crystal was measured to 2θ = 56.5°; however, as the refinement converged to R >> 7%, an OMIT −3 50 instruction was used to eliminate the high angle reflections. For (II), one of the butyl chains is disordered over two positions, and this was refined as two half-site occupancy chains sharing a common C/a atom; the distances were similarly DFIXed.

Computing details top

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPII (Johnson, 1976) for (I); ORTEP-II (Johnson, 1976) for (II). For both compounds, software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP (Johnson, 1976) plot of molecules a and b of (I) at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radii. For a, symmetry code: (i) x, 1/2 − y, z − 1/2. For b, symmetry code: (i) x, 1/2 − y, z + 1/2.
[Figure 2] Fig. 2. ORTEP (Johnson, 1976) plot of (II) at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radii [symmetry code: (i) x − 1/2, 1/2 − y, z − 1/2].
(I) Dicyclohexylammonium 4-oxo-4H-pyran-2,6-dicarboxylatotributylstannate top
Crystal data top
(C12H24N)[Sn(C7H2O6)(C4H9)3]F(000) = 2752
Mr = 654.43Dx = 1.228 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.1212 (3) ÅCell parameters from 7059 reflections
b = 18.0363 (2) Åθ = 1.1–28.3°
c = 21.8937 (1) ŵ = 0.76 mm1
β = 98.454 (1)°T = 298 K
V = 7078.0 (1) Å3Parallelepiped, colorless
Z = 80.38 × 0.24 × 0.20 mm
Data collection top
Siemens CCD area-detector
diffractometer
12367 independent reflections
Radiation source: fine-focus sealed tube6929 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scanθmax = 25.0°, θmin = 1.1°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 2115
Tmin = 0.761, Tmax = 0.863k = 1921
36773 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0667P)2 + 9.8444P]
where P = (Fo2 + 2Fc2)/3
12367 reflections(Δ/σ)max < 0.001
703 parametersΔρmax = 0.74 e Å3
330 restraintsΔρmin = 0.43 e Å3
Crystal data top
(C12H24N)[Sn(C7H2O6)(C4H9)3]V = 7078.0 (1) Å3
Mr = 654.43Z = 8
Monoclinic, P21/cMo Kα radiation
a = 18.1212 (3) ŵ = 0.76 mm1
b = 18.0363 (2) ÅT = 298 K
c = 21.8937 (1) Å0.38 × 0.24 × 0.20 mm
β = 98.454 (1)°
Data collection top
Siemens CCD area-detector
diffractometer
12367 independent reflections
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
6929 reflections with I > 2σ(I)
Tmin = 0.761, Tmax = 0.863Rint = 0.055
36773 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068330 restraints
wR(F2) = 0.189H-atom parameters constrained
S = 1.07Δρmax = 0.74 e Å3
12367 reflectionsΔρmin = 0.43 e Å3
703 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn1a0.38443 (3)0.24258 (3)0.01880 (2)0.0833 (2)
O1a0.3738 (3)0.1835 (3)0.0718 (2)0.091 (2)
O2a0.4280 (3)0.2729 (3)0.1329 (2)0.084 (1)
O3a0.3824 (4)0.1968 (3)0.3890 (2)0.111 (2)
O4a0.4461 (4)0.2755 (3)0.3372 (2)0.104 (2)
O5a0.3999 (2)0.2044 (2)0.2324 (2)0.061 (1)
O6a0.3131 (3)0.0031 (3)0.2297 (2)0.105 (2)
N1a0.4960 (3)0.3469 (3)0.2380 (2)0.068 (1)
C1a0.3274 (6)0.1500 (6)0.0637 (4)0.139 (4)
C2a0.2441 (7)0.1542 (8)0.0599 (7)0.212 (5)
C3a0.2025 (7)0.0856 (8)0.0853 (8)0.233 (6)
C4a0.1195 (7)0.1001 (9)0.0904 (8)0.254 (8)
C5a0.5030 (6)0.2388 (6)0.0000 (5)0.141 (4)
C6a0.5256 (8)0.1562 (7)0.0011 (8)0.233 (6)
C7a0.6077 (8)0.1408 (9)0.010 (1)0.301 (8)
C8a0.614 (1)0.059 (1)0.007 (1)0.33 (1)
C9a0.3191 (7)0.3291 (6)0.0063 (5)0.161 (4)
C10a0.324 (1)0.4106 (8)0.007 (1)0.312 (8)
C11a0.403 (1)0.436 (1)0.021 (1)0.34 (1)
C12a0.408 (2)0.512 (1)0.014 (2)0.53 (2)
C13a0.3950 (4)0.2137 (4)0.1231 (3)0.071 (2)
C14a0.3790 (3)0.1678 (4)0.1780 (2)0.055 (2)
C15a0.3483 (4)0.1013 (4)0.1748 (3)0.065 (2)
C16a0.3360 (4)0.0605 (4)0.2304 (3)0.074 (2)
C17a0.3549 (4)0.1038 (4)0.2862 (3)0.072 (2)
C18a0.3852 (4)0.1700 (4)0.2853 (2)0.064 (2)
C19a0.4082 (5)0.2209 (5)0.3417 (3)0.081 (2)
C20a0.4675 (4)0.4239 (4)0.2426 (3)0.081 (2)
C21a0.4933 (4)0.4564 (4)0.3065 (4)0.109 (3)
C22a0.4613 (5)0.5341 (5)0.3125 (5)0.147 (4)
C23a0.3763 (5)0.5325 (6)0.2983 (6)0.163 (5)
C24a0.3508 (5)0.5009 (5)0.2338 (5)0.158 (5)
C25a0.3823 (4)0.4225 (4)0.2285 (4)0.102 (3)
C26a0.5778 (4)0.3393 (4)0.2344 (3)0.081 (2)
C27a0.6010 (4)0.2601 (4)0.2505 (5)0.125 (3)
C28a0.6843 (5)0.2496 (7)0.2483 (6)0.165 (5)
C29a0.7005 (5)0.2689 (6)0.1840 (6)0.148 (5)
C30a0.6769 (4)0.3481 (6)0.1661 (5)0.133 (4)
C31a0.5945 (4)0.3611 (5)0.1709 (3)0.105 (3)
Sn1b0.88239 (4)0.27728 (3)0.45858 (2)0.1011 (3)
O1b0.8709 (4)0.2207 (3)0.3642 (2)0.113 (2)
O2b0.9337 (4)0.2965 (3)0.3101 (2)0.109 (2)
O3b0.8857 (3)0.1692 (3)0.0539 (2)0.106 (2)
O4b0.9351 (4)0.2662 (3)0.1076 (2)0.101 (2)
O5b0.9012 (2)0.2109 (2)0.2110 (2)0.068 (1)
O6b0.8210 (3)0.0027 (3)0.2234 (3)0.111 (2)
N1b0.9903 (3)0.3531 (3)0.2080 (2)0.071 (1)
C1b0.8083 (7)0.1914 (8)0.4868 (5)0.189 (5)
C2b0.7364 (9)0.201 (1)0.4416 (9)0.301 (8)
C3b0.687 (1)0.134 (1)0.447 (1)0.39 (1)
C4b0.617 (1)0.137 (2)0.398 (1)0.47 (2)
C5b0.9993 (6)0.2498 (6)0.4712 (5)0.133 (3)
C6b1.0086 (7)0.1642 (6)0.4733 (7)0.192 (5)
C7b1.0904 (8)0.1419 (9)0.4738 (9)0.256 (7)
C8b1.098 (1)0.0579 (9)0.493 (1)0.33 (1)
C9b0.8353 (6)0.3795 (6)0.4219 (4)0.151 (4)
C10b0.8924 (7)0.4417 (6)0.4278 (6)0.174 (4)
C11b0.8562 (7)0.5163 (6)0.4056 (7)0.202 (5)
C12b0.9200 (9)0.5724 (8)0.4079 (8)0.249 (8)
C13b0.8978 (5)0.2405 (5)0.3170 (3)0.087 (2)
C14b0.8822 (4)0.1849 (4)0.2653 (2)0.065 (2)
C15b0.8543 (4)0.1175 (4)0.2705 (3)0.073 (2)
C16b0.8415 (4)0.0668 (4)0.2189 (3)0.076 (2)
C17b0.8580 (4)0.0989 (4)0.1624 (3)0.073 (2)
C18b0.8863 (4)0.1665 (4)0.1600 (2)0.064 (2)
C19b0.9056 (5)0.2054 (4)0.1029 (3)0.082 (2)
C20b0.9556 (3)0.4269 (4)0.1938 (3)0.079 (2)
C21b0.9762 (5)0.4823 (4)0.2459 (4)0.127 (4)
C22b0.9406 (5)0.5584 (4)0.2278 (6)0.161 (5)
C23b0.8562 (5)0.5512 (5)0.2137 (5)0.141 (4)
C24b0.8342 (5)0.4945 (5)0.1631 (5)0.124 (3)
C25b0.8704 (4)0.4192 (4)0.1804 (4)0.100 (3)
C26b1.0735 (4)0.3487 (4)0.2144 (3)0.086 (2)
C27b1.1023 (4)0.3733 (5)0.1561 (4)0.117 (3)
C28b1.1876 (4)0.3627 (6)0.1608 (5)0.148 (4)
C29b1.2098 (6)0.2840 (7)0.1812 (7)0.198 (8)
C30b1.1831 (6)0.2621 (7)0.2417 (7)0.197 (8)
C31b1.0969 (5)0.2701 (4)0.2343 (6)0.149 (5)
H1a10.47040.32550.20420.102*
H1a20.48600.32110.27100.102*
H1a30.33490.14910.10660.209*
H1a40.34770.10460.04430.209*
H2a10.23720.16080.01710.318*
H2a20.22320.19720.08290.318*
H3a10.21620.04380.05810.350*
H3a20.21540.07380.12570.350*
H4a10.09260.05710.10730.382*
H4a20.10650.14180.11700.382*
H4a30.10690.11040.05020.382*
H5a10.52460.26500.03180.211*
H5a20.52050.26180.03950.211*
H6a10.50430.13190.03400.349*
H6a20.50350.13380.03750.349*
H7a10.62950.14920.05280.451*
H7a20.63270.17220.01630.451*
H8a10.66540.04640.00610.493*
H8a20.58770.05130.04810.493*
H8a30.59220.02890.02150.493*
H9a10.26820.31550.01000.242*
H9a20.32280.32570.05080.242*
H10a0.28710.43780.01140.468*
H10b0.31590.41930.05130.468*
H11a0.44100.40160.01170.512*
H11b0.40750.44360.06490.512*
H12a0.45470.53520.00040.793*
H12b0.36770.54310.00670.793*
H12c0.40460.50220.05770.793*
H15a0.33400.07980.13630.098*
H17a0.34530.08440.32360.108*
H20a0.48680.45480.21180.122*
H21a0.54740.45880.31370.163*
H21b0.47740.42420.33770.163*
H22a0.47640.55240.35410.220*
H22b0.48090.56740.28410.220*
H23a0.35690.58240.30070.244*
H23b0.35650.50230.32880.244*
H24a0.36780.53290.20310.237*
H24b0.29670.49920.22590.237*
H25a0.36260.38970.25730.153*
H25b0.36700.40360.18710.153*
H26a0.60550.37250.26510.121*
H27a0.57250.22650.22150.187*
H27b0.59030.24840.29160.187*
H28a0.71320.28150.27860.247*
H28b0.69850.19860.25810.247*
H29a0.67400.23470.15430.223*
H29b0.75350.26330.18260.223*
H30a0.68540.35770.12410.200*
H30b0.70720.38250.19310.200*
H31a0.58240.41300.16340.157*
H31b0.56370.33200.13970.157*
H1b10.97120.32150.17800.107*
H1b20.97640.33680.24350.107*
H1b30.82920.14240.48330.284*
H1b40.79970.19910.52900.284*
H2b10.71060.24570.45150.451*
H2b20.74760.20550.39980.451*
H3b10.67330.13160.48780.582*
H3b20.71530.08890.44070.582*
H4b10.59070.09050.39740.705*
H4b20.63050.14650.35820.705*
H4b30.58480.17610.40860.705*
H5b11.02220.27000.43740.200*
H5b21.02400.27130.50940.200*
H6b10.99120.14500.51000.288*
H6b20.97820.14250.43750.288*
H7b11.12270.17200.50310.384*
H7b21.10460.14900.43310.384*
H8b11.14880.04250.49450.497*
H8b21.06660.02840.46280.497*
H8b31.08250.05130.53260.497*
H9b10.81530.37270.37870.227*
H9b20.79440.39330.44360.227*
H10c0.93140.42970.40350.261*
H10d0.91510.44620.47060.261*
H11c0.83010.51180.36380.303*
H11d0.82100.53200.43230.303*
H12d0.90030.61980.39390.373*
H12e0.95490.55580.38180.373*
H12f0.94500.57670.44960.373*
H15b0.84260.10250.30860.109*
H17b0.84860.07130.12620.110*
H20b0.97310.44630.15670.118*
H21c1.03000.48750.25450.191*
H21d0.95870.46450.28310.191*
H22c0.95360.59320.26140.241*
H22d0.95980.57730.19180.241*
H23c0.83670.53620.25070.212*
H23d0.83470.59890.20080.212*
H24c0.84960.51190.12500.187*
H24d0.78040.48910.15620.187*
H25c0.85710.38450.14670.150*
H25d0.85190.39980.21650.150*
H26b1.09410.38240.24770.129*
H27c1.09020.42520.14850.176*
H27d1.07760.34490.12130.176*
H28c1.20300.37250.12100.221*
H28d1.21290.39780.19040.221*
H29c1.26370.27970.18620.296*
H29d1.18910.24970.14910.296*
H30c1.20620.29390.27490.296*
H30d1.19720.21130.25200.296*
H31c1.07390.23510.20370.223*
H31d1.07990.25890.27330.223*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn1a0.1075 (4)0.1069 (4)0.0382 (2)0.0017 (3)0.0198 (2)0.0033 (2)
O1a0.129 (4)0.110 (4)0.034 (2)0.027 (3)0.017 (2)0.008 (2)
O2a0.112 (4)0.091 (3)0.049 (2)0.028 (3)0.012 (2)0.004 (2)
O3a0.175 (5)0.123 (4)0.041 (3)0.031 (4)0.040 (3)0.008 (2)
O4a0.147 (5)0.117 (4)0.050 (3)0.038 (4)0.020 (3)0.011 (3)
O5a0.076 (3)0.075 (3)0.034 (2)0.000 (2)0.015 (2)0.001 (2)
O6a0.154 (5)0.070 (3)0.098 (4)0.015 (3)0.039 (3)0.005 (3)
N1a0.066 (4)0.076 (4)0.063 (3)0.010 (3)0.014 (3)0.008 (2)
C1a0.160 (8)0.178 (8)0.082 (5)0.043 (8)0.023 (6)0.029 (6)
C2a0.23 (1)0.22 (1)0.182 (9)0.04 (1)0.021 (9)0.085 (8)
C3a0.23 (1)0.24 (1)0.22 (1)0.03 (1)0.02 (1)0.09 (1)
C4a0.22 (1)0.27 (1)0.27 (1)0.03 (1)0.02 (1)0.10 (1)
C5a0.145 (8)0.177 (9)0.105 (7)0.009 (7)0.037 (6)0.007 (6)
C6a0.19 (1)0.26 (1)0.25 (1)0.02 (1)0.05 (1)0.07 (1)
C7a0.30 (1)0.30 (1)0.31 (1)0.00 (1)0.07 (1)0.04 (1)
C8a0.34 (2)0.30 (2)0.35 (2)0.01 (2)0.05 (2)0.00 (2)
C9a0.22 (1)0.172 (9)0.100 (6)0.050 (9)0.053 (7)0.021 (6)
C10a0.33 (1)0.31 (1)0.30 (1)0.02 (1)0.08 (1)0.01 (1)
C11a0.33 (2)0.33 (2)0.36 (2)0.00 (1)0.06 (1)0.01 (1)
C12a0.52 (2)0.52 (2)0.55 (2)0.03 (2)0.09 (2)0.00 (2)
C13a0.082 (5)0.090 (5)0.044 (4)0.000 (4)0.020 (3)0.000 (3)
C14a0.059 (4)0.071 (4)0.036 (3)0.007 (3)0.008 (3)0.001 (2)
C15a0.074 (4)0.072 (4)0.051 (3)0.002 (4)0.016 (3)0.003 (3)
C16a0.095 (5)0.066 (5)0.066 (4)0.004 (4)0.025 (4)0.004 (3)
C17a0.095 (5)0.072 (5)0.053 (4)0.002 (4)0.023 (3)0.009 (3)
C18a0.069 (4)0.087 (5)0.039 (3)0.011 (4)0.017 (3)0.005 (3)
C19a0.105 (6)0.100 (6)0.040 (4)0.003 (5)0.020 (4)0.004 (3)
C20a0.083 (6)0.072 (5)0.092 (5)0.005 (4)0.030 (4)0.006 (4)
C21a0.095 (6)0.109 (7)0.128 (7)0.020 (5)0.033 (5)0.047 (5)
C22a0.114 (8)0.112 (8)0.22 (1)0.010 (6)0.046 (8)0.070 (8)
C23a0.13 (1)0.105 (8)0.27 (2)0.002 (7)0.08 (1)0.064 (9)
C24a0.113 (8)0.13 (1)0.24 (2)0.034 (7)0.069 (9)0.005 (9)
C25a0.081 (6)0.104 (6)0.123 (7)0.006 (5)0.024 (5)0.006 (5)
C26a0.069 (5)0.086 (5)0.086 (5)0.001 (4)0.008 (4)0.015 (4)
C27a0.087 (7)0.113 (7)0.17 (1)0.021 (6)0.019 (6)0.024 (6)
C28a0.115 (9)0.18 (1)0.20 (1)0.060 (8)0.024 (9)0.00 (1)
C29a0.085 (7)0.14 (1)0.22 (1)0.012 (7)0.040 (8)0.067 (9)
C30a0.090 (7)0.150 (9)0.17 (1)0.008 (7)0.065 (6)0.028 (8)
C31a0.078 (6)0.138 (7)0.107 (6)0.001 (5)0.044 (5)0.004 (5)
Sn1b0.1472 (6)0.1153 (5)0.0449 (3)0.0084 (4)0.0284 (3)0.0004 (2)
O1b0.157 (5)0.143 (5)0.044 (3)0.033 (4)0.032 (3)0.011 (3)
O2b0.165 (6)0.112 (4)0.054 (3)0.031 (4)0.028 (3)0.010 (3)
O3b0.178 (6)0.098 (4)0.046 (3)0.020 (4)0.026 (3)0.007 (2)
O4b0.170 (6)0.086 (4)0.051 (3)0.027 (4)0.033 (3)0.000 (2)
O5b0.089 (3)0.077 (3)0.040 (2)0.006 (2)0.016 (2)0.000 (2)
O6b0.143 (5)0.082 (4)0.120 (4)0.016 (4)0.059 (4)0.007 (3)
N1b0.077 (4)0.071 (4)0.068 (3)0.006 (3)0.022 (3)0.003 (3)
C1b0.20 (1)0.27 (1)0.099 (7)0.09 (1)0.024 (7)0.003 (8)
C2b0.32 (1)0.33 (1)0.27 (1)0.09 (1)0.10 (1)0.04 (1)
C3b0.40 (2)0.39 (2)0.37 (2)0.05 (1)0.04 (1)0.02 (1)
C4b0.48 (2)0.47 (2)0.46 (2)0.03 (2)0.05 (2)0.01 (2)
C5b0.141 (7)0.169 (8)0.098 (6)0.036 (7)0.044 (6)0.009 (6)
C6b0.178 (9)0.22 (1)0.186 (9)0.037 (9)0.037 (8)0.024 (9)
C7b0.25 (1)0.26 (1)0.25 (1)0.04 (1)0.03 (1)0.04 (1)
C8b0.34 (2)0.33 (2)0.32 (2)0.06 (2)0.06 (1)0.03 (2)
C9b0.19 (1)0.176 (9)0.082 (6)0.006 (8)0.010 (6)0.005 (6)
C10b0.22 (1)0.164 (9)0.129 (7)0.004 (8)0.000 (7)0.033 (7)
C11b0.24 (1)0.20 (1)0.149 (9)0.01 (1)0.004 (9)0.018 (9)
C12b0.30 (2)0.21 (1)0.22 (1)0.04 (1)0.01 (1)0.01 (1)
C13b0.114 (6)0.101 (6)0.047 (4)0.000 (5)0.016 (4)0.002 (4)
C14b0.072 (4)0.086 (5)0.038 (3)0.003 (4)0.013 (3)0.011 (3)
C15b0.073 (5)0.094 (5)0.055 (4)0.008 (4)0.022 (3)0.015 (3)
C16b0.079 (5)0.077 (5)0.079 (5)0.001 (4)0.030 (4)0.009 (4)
C17b0.091 (5)0.073 (5)0.060 (4)0.004 (4)0.025 (3)0.005 (3)
C18b0.074 (4)0.077 (5)0.041 (3)0.002 (4)0.008 (3)0.001 (3)
C19b0.122 (6)0.083 (5)0.043 (4)0.005 (5)0.025 (4)0.002 (3)
C20b0.073 (5)0.077 (5)0.089 (5)0.008 (4)0.022 (4)0.006 (4)
C21b0.099 (7)0.099 (7)0.18 (1)0.004 (6)0.000 (6)0.046 (6)
C22b0.095 (8)0.089 (7)0.30 (2)0.010 (6)0.019 (8)0.046 (8)
C23b0.107 (8)0.105 (7)0.22 (1)0.006 (6)0.033 (8)0.017 (8)
C24b0.084 (6)0.132 (8)0.156 (9)0.011 (6)0.014 (6)0.025 (7)
C25b0.078 (6)0.094 (6)0.129 (7)0.004 (5)0.020 (5)0.000 (5)
C26b0.079 (5)0.082 (5)0.095 (5)0.005 (4)0.009 (4)0.008 (4)
C27b0.089 (6)0.152 (8)0.119 (7)0.003 (6)0.041 (5)0.011 (6)
C28b0.084 (7)0.19 (1)0.18 (1)0.004 (7)0.046 (7)0.032 (9)
C29b0.109 (9)0.13 (1)0.35 (2)0.039 (9)0.02 (1)0.07 (1)
C30b0.12 (1)0.14 (1)0.33 (2)0.038 (9)0.01 (1)0.06 (1)
C31b0.115 (9)0.087 (7)0.24 (1)0.016 (6)0.007 (8)0.023 (7)
Geometric parameters (Å, º) top
Sn1a—C1a2.127 (9)C6a—H6a10.9700
Sn1a—C5a2.13 (1)C6a—H6a20.9700
Sn1a—C9a2.08 (1)C7a—H7a10.9700
Sn1a—O1a2.285 (4)C7a—H7a20.9700
Sn1a—O3ai2.292 (4)C8a—H8a10.9600
O1a—C13a1.256 (8)C8a—H8a20.9600
O2a—C13a1.226 (8)C8a—H8a30.9600
O3a—C19a1.274 (8)C9a—H9a10.9700
O4a—C19a1.213 (8)C9a—H9a20.9700
O5a—C14a1.365 (6)C10a—H10a0.9700
O5a—C18a1.376 (7)C10a—H10b0.9700
O6a—C16a1.220 (8)C11a—H11a0.9700
N1a—C20a1.490 (8)C11a—H11b0.9700
N1a—C26a1.501 (8)C12a—H12a0.9600
C1a—C2a1.525 (9)C12a—H12b0.9600
C2a—C3a1.513 (9)C12a—H12c0.9600
C3a—C4a1.514 (9)C15a—H15a0.9300
C5a—C6a1.544 (9)C17a—H17a0.9300
C6a—C7a1.497 (9)C20a—H20a0.9800
C7a—C8a1.53 (1)C21a—H21a0.9700
C9a—C10a1.50 (1)C21a—H21b0.9700
C10a—C11a1.54 (1)C22a—H22a0.9700
C11a—C12a1.56 (1)C22a—H22b0.9700
C13a—C14a1.523 (8)C23a—H23a0.9700
C14a—C15a1.319 (8)C23a—H23b0.9700
C15a—C16a1.467 (9)C24a—H24a0.9700
C16a—C17a1.449 (9)C24a—H24b0.9700
C17a—C18a1.315 (9)C25a—H25a0.9700
C18a—C19a1.544 (9)C25a—H25b0.9700
C20a—C21a1.525 (7)C26a—H26a0.9800
C20a—C25a1.530 (7)C27a—H27a0.9700
C21a—C22a1.529 (8)C27a—H27b0.9700
C22a—C23a1.527 (8)C28a—H28a0.9700
C23a—C24a1.530 (9)C28a—H28b0.9700
C24a—C25a1.536 (8)C29a—H29a0.9700
C26a—C27a1.516 (7)C29a—H29b0.9700
C26a—C31a1.519 (7)C30a—H30a0.9700
C27a—C28a1.530 (8)C30a—H30b0.9700
C28a—C29a1.521 (9)C31a—H31a0.9700
C29a—C30a1.527 (8)C31a—H31b0.9700
C30a—C31a1.530 (7)N1b—H1b10.9000
Sn1b—C1b2.20 (1)N1b—H1b20.9000
Sn1b—C5b2.15 (1)C1b—H1b30.9700
Sn1b—C9b2.14 (1)C1b—H1b40.9700
Sn1b—O1b2.286 (5)C2b—H2b10.9700
Sn1b—O3bii2.292 (5)C2b—H2b20.9700
O1b—C13b1.258 (9)C3b—H3b10.9700
O2b—C13b1.223 (9)C3b—H3b20.9700
O3b—C19b1.262 (8)C4b—H4b10.9600
O4b—C19b1.218 (8)C4b—H4b20.9600
O5b—C18b1.367 (7)C4b—H4b30.9600
O5b—C14b1.369 (7)C5b—H5b10.9700
O6b—C16b1.222 (8)C5b—H5b20.9700
N1b—C20b1.486 (8)C6b—H6b10.9700
N1b—C26b1.495 (8)C6b—H6b20.9700
C1b—C2b1.53 (1)C7b—H7b10.9700
C2b—C3b1.52 (1)C7b—H7b20.9700
C3b—C4b1.54 (1)C8b—H8b10.9600
C5b—C6b1.552 (9)C8b—H8b20.9600
C6b—C7b1.534 (9)C8b—H8b30.9600
C7b—C8b1.57 (1)C9b—H9b10.9700
C9b—C10b1.519 (9)C9b—H9b20.9700
C10b—C11b1.544 (9)C10b—H10c0.9700
C11b—C12b1.531 (9)C10b—H10d0.9700
C13b—C14b1.51 (1)C11b—H11c0.9700
C14b—C15b1.327 (9)C11b—H11d0.9700
C15b—C16b1.445 (9)C12b—H12d0.9600
C18b—C19b1.520 (9)C12b—H12e0.9600
C20b—C21b1.521 (7)C12b—H12f0.9600
C20b—C25b1.534 (7)C15b—H15b0.9300
C21b—C22b1.542 (8)C17b—H17b0.9300
C22b—C23b1.519 (8)C20b—H20b0.9800
C23b—C24b1.516 (8)C21b—H21c0.9700
C24b—C25b1.532 (8)C21b—H21d0.9700
C26b—C27b1.516 (7)C22b—H22c0.9700
C26b—C31b1.524 (7)C22b—H22d0.9700
C27b—C28b1.545 (8)C23b—H23c0.9700
C28b—C29b1.524 (9)C23b—H23d0.9700
C29b—C30b1.527 (9)C24b—H24c0.9700
C30b—C31b1.552 (9)C24b—H24d0.9700
N1a—H1a10.9000C25b—H25c0.9700
N1a—H1a20.9000C25b—H25d0.9700
C1a—H1a30.9700C26b—H26b0.9800
C1a—H1a40.9700C27b—H27c0.9700
C2a—H2a10.9700C27b—H27d0.9700
C2a—H2a20.9700C28b—H28c0.9700
C3a—H3a10.9700C28b—H28d0.9700
C3a—H3a20.9700C29b—H29c0.9700
C4a—H4a10.9600C29b—H29d0.9700
C4a—H4a20.9600C30b—H30c0.9700
C4a—H4a30.9600C30b—H30d0.9700
C5a—H5a10.9700C31b—H31c0.9700
C5a—H5a20.9700C31b—H31d0.9700
C1a—Sn1a—C5a118.2 (4)N1a—C20a—H20a108.7
C1a—Sn1a—C9a117.0 (5)C21a—C20a—H20a108.7
C1a—Sn1a—O1a86.5 (3)C25a—C20a—H20a108.7
C1a—Sn1a—O3ai91.4 (3)C20a—C21a—H21a109.4
C5a—Sn1a—C9a124.8 (5)C22a—C21a—H21a109.4
C5a—Sn1a—O1a91.6 (3)C20a—C21a—H21b109.4
C5a—Sn1a—O3ai94.0 (3)C22a—C21a—H21b109.4
C9a—Sn1a—O1a89.8 (3)H21a—C21a—H21b108.0
C9a—Sn1a—O3ai86.5 (3)C23a—C22a—H22a109.6
O1a—Sn1a—O3ai174.3 (2)C21a—C22a—H22a109.6
C13a—O1a—Sn1a121.3 (5)C23a—C22a—H22b109.6
C19a—O3a—Sn1aii126.4 (5)C21a—C22a—H22b109.6
C14a—O5a—C18a117.0 (5)H22a—C22a—H22b108.1
C20a—N1a—C26a116.3 (5)C22a—C23a—H23a109.5
C2a—C1a—Sn1a110.7 (7)C24a—C23a—H23a109.5
C3a—C2a—C1a113 (1)C22a—C23a—H23b109.5
C2a—C3a—C4a109 (1)C24a—C23a—H23b109.5
C6a—C5a—Sn1a107.0 (8)H23a—C23a—H23b108.1
C7a—C6a—C5a116 (1)C23a—C24a—H24a109.6
C6a—C7a—C8a105 (1)C25a—C24a—H24a109.6
C10a—C9a—Sn1a129 (1)C23a—C24a—H24b109.6
C9a—C10a—C11a107 (1)C25a—C24a—H24b109.6
C10a—C11a—C12a101 (1)H24a—C24a—H24b108.1
O2a—C13a—O1a127.7 (6)C20a—C25a—H25a109.6
O2a—C13a—C14a118.7 (6)C24a—C25a—H25a109.6
O1a—C13a—C14a113.6 (6)C20a—C25a—H25b109.6
C15a—C14a—O5a123.2 (5)C24a—C25a—H25b109.6
C15a—C14a—C13a125.5 (5)H25a—C25a—H25b108.1
O5a—C14a—C13a111.3 (5)N1a—C26a—H26a108.6
C14a—C15a—C16a121.7 (6)C27a—C26a—H26a108.6
O6a—C16a—C17a123.7 (6)C31a—C26a—H26a108.6
O6a—C16a—C15a123.6 (6)C26a—C27a—H27a109.5
C17a—C16a—C15a112.6 (6)C28a—C27a—H27a109.5
C18a—C17a—C16a121.6 (6)C26a—C27a—H27b109.5
C17a—C18a—O5a123.7 (5)C28a—C27a—H27b109.5
C17a—C18a—C19a126.3 (6)H27a—C27a—H27b108.1
O5a—C18a—C19a110.0 (6)C29a—C28a—H28a109.9
O4a—C19a—O3a128.5 (7)C27a—C28a—H28a109.9
O4a—C19a—C18a120.5 (6)C29a—C28a—H28b109.9
O3a—C19a—C18a111.0 (7)C27a—C28a—H28b109.9
N1a—C20a—C21a111.0 (6)H28a—C28a—H28b108.3
N1a—C20a—C25a108.7 (5)C28a—C29a—H29a109.3
C21a—C20a—C25a110.8 (6)C30a—C29a—H29a109.3
C20a—C21a—C22a111.2 (7)C28a—C29a—H29b109.3
C23a—C22a—C21a110.5 (7)C30a—C29a—H29b109.3
C22a—C23a—C24a110.7 (8)H29a—C29a—H29b108.0
C23a—C24a—C25a110.4 (7)C29a—C30a—H30a109.3
C20a—C25a—C24a110.2 (6)C31a—C30a—H30a109.3
N1a—C26a—C27a108.4 (6)C29a—C30a—H30b109.3
N1a—C26a—C31a110.8 (5)C31a—C30a—H30b109.3
C27a—C26a—C31a111.7 (6)H30a—C30a—H30b108.0
C26a—C27a—C28a110.5 (7)C26a—C31a—H31a109.5
C29a—C28a—C27a109.1 (8)C30a—C31a—H31a109.5
C28a—C29a—C30a111.4 (8)C26a—C31a—H31b109.5
C29a—C30a—C31a111.4 (7)C30a—C31a—H31b109.5
C26a—C31a—C30a110.5 (6)H31a—C31a—H31b108.1
C1b—Sn1b—C5b115.6 (5)C20b—N1b—H1b1108.0
C1b—Sn1b—C9b119.1 (5)C26b—N1b—H1b1108.0
C1b—Sn1b—O1b87.8 (4)C20b—N1b—H1b2108.0
C1b—Sn1b—O3bii88.6 (4)C26b—N1b—H1b2108.0
C5b—Sn1b—C9b125.3 (4)H1b1—N1b—H1b2107.2
C5b—Sn1b—O1b88.3 (3)C2b—C1b—H1b3111.0
C5b—Sn1b—O3bii94.9 (3)Sn1b—C1b—H1b3111.0
C9b—Sn1b—O1b93.8 (3)C2b—C1b—H1b4111.0
C9b—Sn1b—O3bii86.2 (3)Sn1b—C1b—H1b4111.0
O1b—Sn1b—O3bii176.0 (2)H1b3—C1b—H1b4109.0
C13b—O1b—Sn1b128.4 (5)C3b—C2b—H2b1110.1
C19b—O3b—Sn1bi121.4 (5)C1b—C2b—H2b1110.1
C18b—O5b—C14b117.6 (5)C3b—C2b—H2b2110.1
C20b—N1b—C26b117.3 (5)C1b—C2b—H2b2110.1
C2b—C1b—Sn1b103.7 (9)H2b1—C2b—H2b2108.4
C3b—C2b—C1b108 (1)C2b—C3b—H3b1109.5
C2b—C3b—C4b111 (1)C4b—C3b—H3b1109.5
C6b—C5b—Sn1b109.4 (7)C2b—C3b—H3b2109.5
C7b—C6b—C5b111 (1)C4b—C3b—H3b2109.5
C6b—C7b—C8b108 (1)H3b1—C3b—H3b2108.1
C10b—C9b—Sn1b112.1 (7)C3b—C4b—H4b1109.5
C9b—C10b—C11b111.4 (9)C3b—C4b—H4b2109.5
C12b—C11b—C10b106 (1)H4b1—C4b—H4b2109.5
O2b—C13b—O1b127.9 (7)C3b—C4b—H4b3109.5
O2b—C13b—C14b120.1 (7)H4b1—C4b—H4b3109.5
O1b—C13b—C14b112.0 (8)H4b2—C4b—H4b3109.5
C15b—C14b—O5b122.4 (6)C6b—C5b—H5b1109.8
C15b—C14b—C13b125.2 (6)Sn1b—C5b—H5b1109.8
O5b—C14b—C13b112.4 (6)C6b—C5b—H5b2109.8
C14b—C15b—C16b122.1 (6)Sn1b—C5b—H5b2109.8
O6b—C16b—C17b123.6 (7)H5b1—C5b—H5b2108.2
O6b—C16b—C15b123.5 (7)C7b—C6b—H6b1109.4
C17b—C16b—C15b112.9 (6)C5b—C6b—H6b1109.4
C18b—C17b—C16b122.2 (6)C7b—C6b—H6b2109.4
C17b—C18b—O5b122.6 (5)C5b—C6b—H6b2109.4
C17b—C18b—C19b126.4 (6)H6b1—C6b—H6b2108.0
O5b—C18b—C19b111.1 (6)C6b—C7b—H7b1110.2
O4b—C19b—O3b127.3 (6)C8b—C7b—H7b1110.2
O4b—C19b—C18b119.8 (6)C6b—C7b—H7b2110.2
O3b—C19b—C18b112.9 (7)C8b—C7b—H7b2110.2
N1b—C20b—C21b112.5 (6)H7b1—C7b—H7b2108.5
N1b—C20b—C25b110.0 (5)C7b—C8b—H8b1109.5
C21b—C20b—C25b109.5 (6)C7b—C8b—H8b2109.5
C20b—C21b—C22b110.1 (7)H8b1—C8b—H8b2109.5
C23b—C22b—C21b110.3 (7)C7b—C8b—H8b3109.5
C24b—C23b—C22b110.8 (7)H8b1—C8b—H8b3109.5
C23b—C24b—C25b111.1 (7)H8b2—C8b—H8b3109.5
C24b—C25b—C20b110.4 (6)C10b—C9b—H9b1109.2
N1b—C26b—C27b111.9 (6)Sn1b—C9b—H9b1109.2
N1b—C26b—C31b108.1 (6)C10b—C9b—H9b2109.2
C27b—C26b—C31b113.4 (7)Sn1b—C9b—H9b2109.2
C26b—C27b—C28b111.8 (7)H9b1—C9b—H9b2107.9
C29b—C28b—C27b110.7 (7)C9b—C10b—H10c109.3
C28b—C29b—C30b113.0 (9)C11b—C10b—H10c109.3
C29b—C30b—C31b109.1 (9)C9b—C10b—H10d109.3
C26b—C31b—C30b110.5 (7)C11b—C10b—H10d109.3
C20a—N1a—H1a1108.2H10c—C10b—H10d108.0
C26a—N1a—H1a1108.2C12b—C11b—H11c110.5
C20a—N1a—H1a2108.2C10b—C11b—H11c110.5
C26a—N1a—H1a2108.2C12b—C11b—H11d110.5
H1a1—N1a—H1a2107.4C10b—C11b—H11d110.5
C2a—C1a—H1a3109.5H11c—C11b—H11d108.6
Sn1a—C1a—H1a3109.5C11b—C12b—H12d109.5
C2a—C1a—H1a4109.5C11b—C12b—H12e109.5
Sn1a—C1a—H1a4109.5H12d—C12b—H12e109.5
H1a3—C1a—H1a4108.1C11b—C12b—H12f109.5
C3a—C2a—H2a1109.1H12d—C12b—H12f109.5
C1a—C2a—H2a1109.1H12e—C12b—H12f109.5
C3a—C2a—H2a2109.1C14b—C15b—H15b118.9
C1a—C2a—H2a2109.1C16b—C15b—H15b118.9
H2a1—C2a—H2a2107.8C18b—C17b—H17b118.9
C2a—C3a—H3a1109.9C16b—C17b—H17b118.9
C4a—C3a—H3a1109.9N1b—C20b—H20b108.3
C2a—C3a—H3a2109.9C21b—C20b—H20b108.3
C4a—C3a—H3a2109.9C25b—C20b—H20b108.3
H3a1—C3a—H3a2108.3C20b—C21b—H21c109.6
C3a—C4a—H4a1109.5C22b—C21b—H21c109.6
C3a—C4a—H4a2109.5C20b—C21b—H21d109.6
H4a1—C4a—H4a2109.5C22b—C21b—H21d109.6
C3a—C4a—H4a3109.5H21c—C21b—H21d108.1
H4a1—C4a—H4a3109.5C23b—C22b—H22c109.6
H4a2—C4a—H4a3109.5C21b—C22b—H22c109.6
C6a—C5a—H5a1110.3C23b—C22b—H22d109.6
Sn1a—C5a—H5a1110.3C21b—C22b—H22d109.6
C6a—C5a—H5a2110.3H22c—C22b—H22d108.1
Sn1a—C5a—H5a2110.3C24b—C23b—H23c109.5
H5a1—C5a—H5a2108.6C22b—C23b—H23c109.5
C7a—C6a—H6a1108.3C24b—C23b—H23d109.5
C5a—C6a—H6a1108.3C22b—C23b—H23d109.5
C7a—C6a—H6a2108.3H23c—C23b—H23d108.1
C5a—C6a—H6a2108.3C23b—C24b—H24c109.4
H6a1—C6a—H6a2107.4C25b—C24b—H24c109.4
C6a—C7a—H7a1110.8C23b—C24b—H24d109.4
C8a—C7a—H7a1110.8C25b—C24b—H24d109.4
C6a—C7a—H7a2110.8H24c—C24b—H24d108.0
C8a—C7a—H7a2110.8C24b—C25b—H25c109.6
H7a1—C7a—H7a2108.9C20b—C25b—H25c109.6
C7a—C8a—H8a1109.5C24b—C25b—H25d109.6
C7a—C8a—H8a2109.5C20b—C25b—H25d109.6
H8a1—C8a—H8a2109.5H25c—C25b—H25d108.1
C7a—C8a—H8a3109.5N1b—C26b—H26b107.7
H8a1—C8a—H8a3109.5C27b—C26b—H26b107.7
H8a2—C8a—H8a3109.5C31b—C26b—H26b107.7
C10a—C9a—H9a1105.1C26b—C27b—H27c109.3
Sn1a—C9a—H9a1105.1C28b—C27b—H27c109.3
C10a—C9a—H9a2105.1C26b—C27b—H27d109.3
Sn1a—C9a—H9a2105.1C28b—C27b—H27d109.3
H9a1—C9a—H9a2105.9H27c—C27b—H27d107.9
C9a—C10a—H10a110.2C29b—C28b—H28c109.5
C11a—C10a—H10a110.2C27b—C28b—H28c109.5
C9a—C10a—H10b110.2C29b—C28b—H28d109.5
C11a—C10a—H10b110.2C27b—C28b—H28d109.5
H10a—C10a—H10b108.5H28c—C28b—H28d108.1
C10a—C11a—H11a111.6C28b—C29b—H29c109.0
C12a—C11a—H11a111.6C30b—C29b—H29c109.0
C10a—C11a—H11b111.6C28b—C29b—H29d109.0
C12a—C11a—H11b111.6C30b—C29b—H29d109.0
H11a—C11a—H11b109.4H29c—C29b—H29d107.8
C11a—C12a—H12a109.5C29b—C30b—H30c109.9
C11a—C12a—H12b109.5C31b—C30b—H30c109.9
H12a—C12a—H12b109.5C29b—C30b—H30d109.9
C11a—C12a—H12c109.5C31b—C30b—H30d109.9
H12a—C12a—H12c109.5H30c—C30b—H30d108.3
H12b—C12a—H12c109.5C26b—C31b—H31c109.6
C14a—C15a—H15a119.2C30b—C31b—H31c109.6
C16a—C15a—H15a119.2C26b—C31b—H31d109.6
C18a—C17a—H17a119.2C30b—C31b—H31d109.6
C16a—C17a—H17a119.2H31c—C31b—H31d108.1
C9a—Sn1a—O1a—C13a58.3 (6)C9b—Sn1b—O1b—C13b58.0 (8)
C1a—Sn1a—O1a—C13a175.4 (6)C5b—Sn1b—O1b—C13b67.2 (8)
C5a—Sn1a—O1a—C13a66.4 (6)C1b—Sn1b—O1b—C13b177.1 (8)
O3ai—Sn1a—O1a—C13a108 (2)O3bii—Sn1b—O1b—C13b149 (3)
C9a—Sn1a—C1a—C2a11 (1)C9b—Sn1b—C1b—C2b33 (1)
C5a—Sn1a—C1a—C2a166.8 (9)C5b—Sn1b—C1b—C2b147 (1)
O1a—Sn1a—C1a—C2a76.9 (9)O1b—Sn1b—C1b—C2b60 (1)
O3ai—Sn1a—C1a—C2a97.8 (9)O3bii—Sn1b—C1b—C2b118 (1)
Sn1a—C1a—C2a—C3a174 (1)Sn1b—C1b—C2b—C3b167 (2)
C1a—C2a—C3a—C4a170 (1)C1b—C2b—C3b—C4b175 (2)
C9a—Sn1a—C5a—C6a155.2 (9)C9b—Sn1b—C5b—C6b157.5 (8)
C1a—Sn1a—C5a—C6a23 (1)C1b—Sn1b—C5b—C6b22.7 (9)
O1a—Sn1a—C5a—C6a64.2 (9)O1b—Sn1b—C5b—C6b64.0 (8)
O3ai—Sn1a—C5a—C6a116.4 (9)O3bii—Sn1b—C5b—C6b113.6 (8)
Sn1a—C5a—C6a—C7a177 (1)Sn1b—C5b—C6b—C7b173 (1)
C5a—C6a—C7a—C8a166 (2)C5b—C6b—C7b—C8b166 (1)
C1a—Sn1a—C9a—C10a129 (1)C5b—Sn1b—C9b—C10b22 (1)
C5a—Sn1a—C9a—C10a54 (1)C1b—Sn1b—C9b—C10b158.0 (8)
O1a—Sn1a—C9a—C10a146 (1)O1b—Sn1b—C9b—C10b112.4 (8)
O3ai—Sn1a—C9a—C10a39 (1)O3bii—Sn1b—C9b—C10b71.6 (8)
Sn1a—C9a—C10a—C11a58 (2)Sn1b—C9b—C10b—C11b175.8 (9)
C9a—C10a—C11a—C12a163 (2)C9b—C10b—C11b—C12b175 (1)
Sn1a—O1a—C13a—O2a6 (1)Sn1b—O1b—C13b—O2b3 (1)
Sn1a—O1a—C13a—C14a176.4 (4)Sn1b—O1b—C13b—C14b175.6 (5)
C18a—O5a—C14a—C15a2.4 (8)C18b—O5b—C14b—C15b3.9 (9)
C18a—O5a—C14a—C13a177.1 (5)C18b—O5b—C14b—C13b176.9 (6)
O2a—C13a—C14a—C15a175.6 (6)O2b—C13b—C14b—C15b169.0 (8)
O1a—C13a—C14a—C15a2 (1)O1b—C13b—C14b—C15b10 (1)
O2a—C13a—C14a—O5a4.9 (8)O2b—C13b—C14b—O5b10 (1)
O1a—C13a—C14a—O5a177.2 (5)O1b—C13b—C14b—O5b170.7 (6)
O5a—C14a—C15a—C16a2 (1)O5b—C14b—C15b—C16b0 (1)
C13a—C14a—C15a—C16a178.9 (6)C13b—C14b—C15b—C16b179.4 (7)
C14a—C15a—C16a—O6a174.2 (7)C14b—C15b—C16b—O6b174.5 (7)
C14a—C15a—C16a—C17a5.2 (9)C14b—C15b—C16b—C17b3 (1)
O6a—C16a—C17a—C18a174.3 (7)O6b—C16b—C17b—C18b174.1 (7)
C15a—C16a—C17a—C18a5 (1)C15b—C16b—C17b—C18b4 (1)
C16a—C17a—C18a—O5a2 (1)C16b—C17b—C18b—O5b1 (1)
C16a—C17a—C18a—C19a179.4 (6)C16b—C17b—C18b—C19b179.9 (7)
C14a—O5a—C18a—C17a2.5 (9)C14b—O5b—C18b—C17b3.4 (9)
C14a—O5a—C18a—C19a176.7 (5)C14b—O5b—C18b—C19b176.0 (5)
Sn1aii—O3a—C19a—O4a9 (1)Sn1bi—O3b—C19b—O4b12 (1)
Sn1aii—O3a—C19a—C18a170.7 (4)Sn1bi—O3b—C19b—C18b166.1 (4)
C17a—C18a—C19a—O4a168.5 (8)C17b—C18b—C19b—O4b176.0 (7)
O5a—C18a—C19a—O4a12 (1)O5b—C18b—C19b—O4b5 (1)
C17a—C18a—C19a—O3a12 (1)C17b—C18b—C19b—O3b6 (1)
O5a—C18a—C19a—O3a167.6 (6)O5b—C18b—C19b—O3b173.4 (6)
C26a—N1a—C20a—C21a72.8 (7)C26b—N1b—C20b—C21b65.3 (8)
C26a—N1a—C20a—C25a165.1 (6)C26b—N1b—C20b—C25b172.4 (6)
N1a—C20a—C21a—C22a177.4 (6)N1b—C20b—C21b—C22b178.2 (7)
C25a—C20a—C21a—C22a56.5 (9)C25b—C20b—C21b—C22b59.1 (9)
C20a—C21a—C22a—C23a56 (1)C20b—C21b—C22b—C23b59 (1)
C21a—C22a—C23a—C24a57 (1)C21b—C22b—C23b—C24b57 (1)
C22a—C23a—C24a—C25a58 (1)C22b—C23b—C24b—C25b56 (1)
N1a—C20a—C25a—C24a179.2 (7)C23b—C24b—C25b—C20b57 (1)
C21a—C20a—C25a—C24a56.9 (9)N1b—C20b—C25b—C24b177.7 (6)
C23a—C24a—C25a—C20a58 (1)C21b—C20b—C25b—C24b58.2 (9)
C20a—N1a—C26a—C27a162.1 (6)C20b—N1b—C26b—C27b59.3 (8)
C20a—N1a—C26a—C31a75.0 (7)C20b—N1b—C26b—C31b175.1 (7)
N1a—C26a—C27a—C28a179.4 (8)N1b—C26b—C27b—C28b175.4 (7)
C31a—C26a—C27a—C28a58 (1)C31b—C26b—C27b—C28b53 (1)
C26a—C27a—C28a—C29a59 (1)C26b—C27b—C28b—C29b51 (1)
C27a—C28a—C29a—C30a58 (1)C27b—C28b—C29b—C30b55 (1)
C28a—C29a—C30a—C31a56 (1)C28b—C29b—C30b—C31b58 (2)
N1a—C26a—C31a—C30a176.0 (6)N1b—C26b—C31b—C30b179.9 (9)
C27a—C26a—C31a—C30a55.0 (9)C27b—C26b—C31b—C30b55 (1)
C29a—C30a—C31a—C26a54 (1)C29b—C30b—C31b—C26b56 (1)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1a—H1a1···O2a0.901.892.785 (7)172
N1a—H1a2···O4a0.901.902.788 (7)169
N1b—H1b2···O2b0.901.892.786 (8)171
N1b—H1b1···O4b0.901.872.765 (7)172
(II) Methylphenylammonium 2,6-pyridinedicarboxylatotributylstannate top
Crystal data top
(C7H10N)[Sn(C7H3NO4)(C4H9)3]F(000) = 1168
Mr = 563.29Dx = 1.289 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 17.7536 (3) ÅCell parameters from 5832 reflections
b = 9.3746 (1) Åθ = 2.8–28.3°
c = 17.8985 (2) ŵ = 0.91 mm1
β = 102.981 (1)°T = 298 K
V = 2902.77 (7) Å3Block, colorless
Z = 40.44 × 0.22 × 0.18 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
7133 independent reflections
Radiation source: fine-focus sealed tube4770 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω scanθmax = 28.3°, θmin = 2.8°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 2312
Tmin = 0.690, Tmax = 0.853k = 1212
19786 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0751P)2 + 0.3874P]
where P = (Fo2 + 2Fc2)/3
7133 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.88 e Å3
20 restraintsΔρmin = 1.08 e Å3
Crystal data top
(C7H10N)[Sn(C7H3NO4)(C4H9)3]V = 2902.77 (7) Å3
Mr = 563.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 17.7536 (3) ŵ = 0.91 mm1
b = 9.3746 (1) ÅT = 298 K
c = 17.8985 (2) Å0.44 × 0.22 × 0.18 mm
β = 102.981 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
7133 independent reflections
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
4770 reflections with I > 2σ(I)
Tmin = 0.690, Tmax = 0.853Rint = 0.059
19786 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04920 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.06Δρmax = 0.88 e Å3
7133 reflectionsΔρmin = 1.08 e Å3
307 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.41074 (2)0.25654 (2)0.21949 (1)0.0460 (1)
O10.4960 (2)0.1554 (3)0.3195 (2)0.061 (1)
O20.5899 (2)0.3179 (4)0.3319 (2)0.071 (1)
O30.8179 (2)0.1391 (3)0.6270 (1)0.062 (1)
O40.8014 (2)0.3116 (4)0.5384 (2)0.068 (1)
N10.6707 (2)0.1854 (4)0.4594 (2)0.043 (1)
N20.7288 (2)0.4356 (4)0.4011 (2)0.072 (1)
C10.3293 (3)0.0980 (5)0.2371 (3)0.070 (1)
C20.353 (3)0.058 (2)0.247 (2)0.115 (3)0.50
C30.392 (2)0.109 (2)0.185 (1)0.125 (5)0.50
C40.363 (2)0.248 (2)0.146 (1)0.138 (7)0.50
C2'0.355 (3)0.051 (2)0.264 (1)0.115 (3)0.50
C3'0.393 (2)0.138 (2)0.211 (1)0.125 (5)0.50
C4'0.342 (2)0.160 (2)0.131 (1)0.138 (7)0.50
C50.4090 (3)0.4525 (4)0.2817 (2)0.064 (1)
C60.3986 (3)0.4362 (5)0.3629 (3)0.077 (1)
C70.3933 (3)0.5779 (5)0.4035 (3)0.084 (2)
C80.4653 (4)0.6663 (7)0.4168 (3)0.098 (2)
C90.4870 (3)0.2310 (5)0.1452 (3)0.067 (1)
C100.5293 (4)0.3638 (7)0.1289 (3)0.098 (2)
C110.5839 (5)0.3339 (9)0.0762 (5)0.140 (3)
C120.6285 (6)0.461 (1)0.0600 (6)0.193 (5)
C130.5612 (2)0.2092 (4)0.3517 (2)0.049 (1)
C140.6050 (2)0.1260 (4)0.4218 (2)0.042 (1)
C150.5768 (2)0.0004 (4)0.4441 (2)0.055 (1)
C160.6181 (3)0.0649 (5)0.5094 (3)0.069 (1)
C170.6860 (2)0.0047 (4)0.5498 (2)0.055 (1)
C180.7104 (2)0.1210 (4)0.5227 (2)0.042 (1)
C190.7829 (2)0.1973 (5)0.5650 (2)0.049 (1)
C200.7123 (4)0.5856 (6)0.4216 (4)0.107 (2)
C210.7805 (3)0.4203 (6)0.3492 (3)0.076 (1)
C220.7579 (4)0.469 (1)0.2747 (4)0.128 (3)
C230.8104 (6)0.448 (1)0.2269 (4)0.165 (4)
C240.8784 (6)0.390 (1)0.2507 (5)0.132 (3)
C250.9001 (5)0.341 (1)0.3240 (6)0.146 (3)
C260.8496 (4)0.3622 (9)0.3739 (4)0.126 (3)
H2a0.74930.38830.44460.108*
H2b0.68360.39320.37970.108*
H1a0.31140.12560.28240.105*
H1b0.28510.10360.19410.105*
H2c0.38810.07040.29640.172*0.50
H2d0.30770.11570.24570.172*0.50
H3a0.44720.11920.20750.188*0.50
H3b0.38700.03500.14610.188*0.50
H4a0.39170.26940.10720.208*0.50
H4b0.30930.23920.12190.208*0.50
H4c0.37040.32350.18280.208*0.50
H2'10.31100.10290.27250.172*0.50
H2'20.39200.04270.31310.172*0.50
H3'10.40690.23020.23410.188*0.50
H3'20.44000.09050.20600.188*0.50
H4'10.37050.21310.10030.208*0.50
H4'20.32730.06970.10730.208*0.50
H4'30.29670.21300.13460.208*0.50
H5a0.45710.50280.28340.095*
H5b0.36740.51160.25340.095*
H6a0.44170.38200.39240.115*
H6b0.35180.38200.36190.115*
H7a0.35110.63300.37320.126*
H7b0.38090.55860.45260.126*
H8a0.45720.75340.44210.147*
H8b0.47760.68800.36850.147*
H8c0.50720.61430.44830.147*
H9a0.52510.15960.16700.101*
H9b0.45770.19390.09670.101*
H10a0.55860.40250.17700.147*
H10b0.49180.43510.10540.147*
H11a0.62010.26030.09940.211*
H11b0.55400.29690.02800.211*
H12a0.66100.43360.02620.290*
H12b0.65990.49610.10710.290*
H12c0.59330.53370.03630.290*
H150.53120.03930.41590.082*
H160.60020.14950.52640.103*
H170.71450.04750.59400.082*
H20a0.67770.58430.45590.161*
H20b0.68880.63700.37590.161*
H20c0.75970.63160.44610.161*
H220.71050.51330.25680.192*
H230.79570.47690.17590.248*
H240.91190.38210.21770.198*
H250.94720.29530.34100.219*
H260.86520.33460.42490.189*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0373 (2)0.0584 (2)0.0354 (2)0.0001 (1)0.0064 (1)0.0043 (1)
O10.047 (2)0.067 (2)0.054 (2)0.001 (1)0.019 (1)0.003 (1)
O20.052 (2)0.090 (2)0.058 (2)0.012 (2)0.014 (1)0.030 (2)
O30.058 (2)0.074 (2)0.039 (1)0.010 (2)0.017 (1)0.005 (1)
O40.060 (2)0.079 (2)0.054 (2)0.026 (2)0.013 (1)0.011 (2)
N10.039 (2)0.054 (2)0.031 (1)0.004 (1)0.003 (1)0.001 (1)
N20.062 (2)0.083 (3)0.064 (2)0.023 (2)0.000 (2)0.026 (2)
C10.057 (3)0.084 (3)0.066 (3)0.007 (2)0.005 (2)0.004 (2)
C20.105 (6)0.096 (5)0.15 (1)0.025 (5)0.037 (9)0.009 (6)
C30.157 (8)0.091 (7)0.16 (2)0.031 (7)0.09 (1)0.005 (8)
C40.16 (2)0.15 (2)0.10 (1)0.04 (2)0.02 (1)0.00 (1)
C2'0.105 (6)0.096 (5)0.15 (1)0.025 (5)0.037 (9)0.009 (6)
C3'0.157 (8)0.091 (7)0.16 (2)0.031 (7)0.09 (1)0.005 (8)
C4'0.16 (2)0.15 (2)0.10 (1)0.04 (2)0.02 (1)0.00 (1)
C50.075 (3)0.058 (2)0.047 (2)0.002 (2)0.009 (2)0.006 (2)
C60.089 (4)0.072 (3)0.075 (3)0.019 (3)0.030 (3)0.022 (2)
C70.084 (4)0.081 (3)0.088 (3)0.004 (3)0.025 (3)0.030 (3)
C80.095 (4)0.110 (4)0.089 (4)0.030 (4)0.020 (3)0.039 (3)
C90.058 (3)0.086 (3)0.059 (3)0.002 (2)0.014 (2)0.000 (2)
C100.095 (4)0.123 (5)0.079 (4)0.020 (4)0.024 (3)0.009 (3)
C110.161 (8)0.148 (7)0.141 (7)0.021 (6)0.094 (6)0.007 (6)
C120.170 (9)0.26 (1)0.159 (8)0.071 (9)0.057 (7)0.074 (8)
C130.040 (2)0.060 (2)0.038 (2)0.001 (2)0.007 (2)0.001 (2)
C140.036 (2)0.052 (2)0.033 (2)0.001 (2)0.003 (1)0.003 (1)
C150.044 (2)0.059 (2)0.053 (2)0.014 (2)0.006 (2)0.001 (2)
C160.062 (3)0.063 (2)0.068 (3)0.015 (2)0.012 (2)0.022 (2)
C170.054 (2)0.056 (2)0.046 (2)0.004 (2)0.004 (2)0.013 (2)
C180.036 (2)0.054 (2)0.032 (2)0.002 (2)0.001 (1)0.002 (1)
C190.040 (2)0.066 (2)0.036 (2)0.005 (2)0.004 (2)0.001 (2)
C200.118 (5)0.087 (4)0.119 (5)0.008 (4)0.031 (4)0.015 (3)
C210.065 (3)0.086 (3)0.072 (3)0.027 (3)0.001 (3)0.019 (2)
C220.087 (5)0.219 (9)0.076 (4)0.011 (5)0.014 (3)0.045 (5)
C230.125 (7)0.29 (1)0.085 (5)0.040 (9)0.022 (5)0.047 (6)
C240.125 (7)0.167 (8)0.114 (6)0.038 (6)0.051 (5)0.003 (5)
C250.116 (6)0.172 (8)0.167 (8)0.023 (6)0.069 (6)0.065 (7)
C260.101 (5)0.167 (7)0.116 (5)0.020 (5)0.036 (4)0.073 (5)
Geometric parameters (Å, º) top
Sn1—C12.146 (5)C2—H2d0.9700
Sn1—C52.152 (4)C3—H3a0.9700
Sn1—C92.113 (5)C3—H3b0.9700
Sn1—O12.275 (2)C4—H4a0.9600
Sn1—O3i2.279 (2)C4—H4b0.9600
O1—C131.275 (5)C4—H4c0.9600
O2—C131.226 (5)C2'—H2'10.9700
O3—C191.266 (4)C2'—H2'20.9700
O4—C191.247 (5)C3'—H3'10.9700
N1—C141.332 (4)C3'—H3'20.9700
N1—C181.336 (4)C4'—H4'10.9600
N2—C211.452 (7)C4'—H4'20.9600
N2—C201.499 (7)C4'—H4'30.9600
C1—C21.519 (9)C5—H5a0.9700
C2—C31.511 (9)C5—H5b0.9700
C3—C41.518 (9)C6—H6a0.9700
C1—C2'1.513 (9)C6—H6b0.9700
C2'—C3'1.515 (9)C7—H7a0.9700
C3'—C4'1.53 (1)C7—H7b0.9700
C5—C61.514 (5)C8—H8a0.9600
C6—C71.527 (5)C8—H8b0.9600
C7—C81.496 (6)C8—H8c0.9600
C9—C101.516 (6)C9—H9a0.9700
C10—C111.523 (7)C9—H9b0.9700
C11—C121.492 (8)C10—H10a0.9700
C13—C141.533 (5)C10—H10b0.9700
C14—C151.373 (5)C11—H11a0.9700
C15—C161.377 (6)C11—H11b0.9700
C16—C171.379 (6)C12—H12a0.9600
C17—C181.380 (5)C12—H12b0.9600
C18—C191.518 (5)C12—H12c0.9600
C21—C261.324 (8)C15—H150.9300
C21—C221.381 (8)C16—H160.9300
C22—C231.41 (1)C17—H170.9300
C23—C241.31 (1)C20—H20a0.9600
C24—C251.36 (1)C20—H20b0.9600
C25—C261.41 (1)C20—H20c0.9600
N2—H2a0.9000C22—H220.9300
N2—H2b0.9000C23—H230.9300
C1—H1a0.9700C24—H240.9300
C1—H1b0.9700C25—H250.9300
C2—H2c0.9700C26—H260.9300
C1—Sn1—C5115.3 (2)H2'1—C2'—H2'2107.4
C1—Sn1—C9124.2 (2)C2'—C3'—H3'1108.6
C1—Sn1—O187.0 (1)C4'—C3'—H3'1108.6
C1—Sn1—O3i90.2 (2)C2'—C3'—H3'2108.6
C5—Sn1—C9120.5 (2)C4'—C3'—H3'2108.6
C5—Sn1—O191.9 (1)H3'1—C3'—H3'2107.6
C5—Sn1—O3i85.3 (1)C3'—C4'—H4'1109.5
C9—Sn1—O192.3 (2)C3'—C4'—H4'2109.5
C9—Sn1—O3i93.0 (2)H4'1—C4'—H4'2109.5
O1—Sn1—O3i174.7 (1)C3'—C4'—H4'3109.5
C13—O1—Sn1124.5 (3)H4'1—C4'—H4'3109.5
C19—O3—Sn1ii125.7 (3)H4'2—C4'—H4'3109.5
C14—N1—C18118.3 (3)C6—C5—H5a108.4
C21—N2—C20115.9 (4)Sn1—C5—H5a108.4
C2—C1—Sn1120 (2)C6—C5—H5b108.4
C3—C2—C1113 (1)Sn1—C5—H5b108.4
C2—C3—C4117 (1)H5a—C5—H5b107.5
C2'—C1—Sn1121 (1)C5—C6—H6a108.8
C3'—C2'—C1116 (1)C7—C6—H6a108.8
C2'—C3'—C4'115 (1)C5—C6—H6b108.8
C6—C5—Sn1115.5 (3)C7—C6—H6b108.8
C5—C6—C7113.8 (4)H6a—C6—H6b107.7
C8—C7—C6114.6 (5)C8—C7—H7a108.6
C10—C9—Sn1116.3 (3)C6—C7—H7a108.6
C9—C10—C11112.3 (5)C8—C7—H7b108.6
C12—C11—C10114.4 (7)C6—C7—H7b108.6
O2—C13—O1126.3 (3)H7a—C7—H7b107.6
O2—C13—C14119.5 (3)C7—C8—H8a109.5
O1—C13—C14114.2 (3)C7—C8—H8b109.5
N1—C14—C15123.2 (3)H8a—C8—H8b109.5
N1—C14—C13115.2 (3)C7—C8—H8c109.5
C15—C14—C13121.6 (3)H8a—C8—H8c109.5
C16—C15—C14118.0 (3)H8b—C8—H8c109.5
C17—C16—C15119.9 (4)C10—C9—H9a108.2
C16—C17—C18118.1 (3)Sn1—C9—H9a108.2
N1—C18—C17122.5 (3)C10—C9—H9b108.2
N1—C18—C19115.8 (3)Sn1—C9—H9b108.2
C17—C18—C19121.6 (3)H9a—C9—H9b107.4
O4—C19—O3125.8 (3)C9—C10—H10a109.1
O4—C19—C18118.8 (3)C11—C10—H10a109.1
O3—C19—C18115.3 (4)C9—C10—H10b109.1
C26—C21—C22120.2 (6)C11—C10—H10b109.1
C26—C21—N2119.9 (5)H10a—C10—H10b107.9
C22—C21—N2119.8 (5)C12—C11—H11a108.7
C21—C22—C23116.9 (7)C10—C11—H11a108.7
C24—C23—C22123.2 (8)C12—C11—H11b108.7
C23—C24—C25119.6 (8)C10—C11—H11b108.7
C24—C25—C26118.8 (8)H11a—C11—H11b107.6
C21—C26—C25121.2 (7)C11—C12—H12a109.5
C21—N2—H2a108.3C11—C12—H12b109.5
C20—N2—H2a108.3H12a—C12—H12b109.5
C21—N2—H2b108.3C11—C12—H12c109.5
C20—N2—H2b108.3H12a—C12—H12c109.5
H2a—N2—H2b107.4H12b—C12—H12c109.5
C2—C1—H1a107.3C16—C15—H15121.0
Sn1—C1—H1a107.3C14—C15—H15121.0
C2—C1—H1b107.3C17—C16—H16120.0
Sn1—C1—H1b107.3C15—C16—H16120.0
H1a—C1—H1b106.9C16—C17—H17120.9
C3—C2—H2c109.1C18—C17—H17120.9
C1—C2—H2c109.1N2—C20—H20a109.5
C3—C2—H2d109.1N2—C20—H20b109.5
C1—C2—H2d109.1H20a—C20—H20b109.5
H2c—C2—H2d107.8N2—C20—H20c109.5
C2—C3—H3a108.1H20a—C20—H20c109.5
C4—C3—H3a108.1H20b—C20—H20c109.5
C2—C3—H3b108.1C21—C22—H22121.6
C4—C3—H3b108.1C23—C22—H22121.6
H3a—C3—H3b107.3C24—C23—H23118.4
C3—C4—H4a109.5C22—C23—H23118.4
C3—C4—H4b109.5C23—C24—H24120.2
H4a—C4—H4b109.5C25—C24—H24120.2
C3—C4—H4c109.5C24—C25—H25120.6
H4a—C4—H4c109.5C26—C25—H25120.6
H4b—C4—H4c109.5C21—C26—H26119.4
C3'—C2'—H2'1108.2C25—C26—H26119.4
C3'—C2'—H2'2108.2
C9—Sn1—O1—C1365.7 (4)O1—C13—C14—N1175.6 (3)
C1—Sn1—O1—C13170.1 (4)O2—C13—C14—C15177.0 (4)
C5—Sn1—O1—C1354.9 (4)O1—C13—C14—C153.4 (6)
O3i—Sn1—O1—C13113 (1)N1—C14—C15—C161.4 (6)
C9—Sn1—C1—C243 (1)C13—C14—C15—C16177.5 (4)
C5—Sn1—C1—C2138 (1)C14—C15—C16—C170.7 (7)
O1—Sn1—C1—C248 (1)C15—C16—C17—C180.0 (7)
O3i—Sn1—C1—C2137 (1)C14—N1—C18—C170.5 (5)
Sn1—C1—C2—C350 (3)C14—N1—C18—C19177.3 (3)
C1—C2—C3—C4131 (3)C16—C17—C18—N10.1 (6)
C9—Sn1—C5—C6141.5 (4)C16—C17—C18—C19177.8 (4)
C1—Sn1—C5—C639.9 (4)Sn1ii—O3—C19—O412.1 (7)
O1—Sn1—C5—C647.6 (4)Sn1ii—O3—C19—C18165.1 (2)
O3i—Sn1—C5—C6127.9 (4)N1—C18—C19—O41.0 (6)
Sn1—C5—C6—C7176.9 (4)C17—C18—C19—O4178.9 (4)
C5—C6—C7—C864.7 (7)N1—C18—C19—O3176.5 (4)
C1—Sn1—C9—C10168.9 (4)C17—C18—C19—O31.4 (6)
C5—Sn1—C9—C109.6 (5)C20—N2—C21—C26113.0 (7)
O1—Sn1—C9—C10103.2 (4)C20—N2—C21—C2265.8 (7)
O3i—Sn1—C9—C1076.7 (4)C26—C21—C22—C233 (1)
Sn1—C9—C10—C11178.8 (5)N2—C21—C22—C23178.8 (8)
C9—C10—C11—C12178.6 (7)C21—C22—C23—C242 (2)
Sn1—O1—C13—O24.2 (7)C22—C23—C24—C253 (2)
Sn1—O1—C13—C14175.4 (2)C23—C24—C25—C264 (2)
C18—N1—C14—C151.3 (5)C22—C21—C26—C254 (1)
C18—N1—C14—C13177.7 (3)N2—C21—C26—C25177.8 (7)
O2—C13—C14—N14.0 (6)C24—C25—C26—C214 (2)
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2b···O20.901.832.732 (5)176
N2—H2a···O40.901.872.763 (4)172

Experimental details

(I)(II)
Crystal data
Chemical formula(C12H24N)[Sn(C7H2O6)(C4H9)3](C7H10N)[Sn(C7H3NO4)(C4H9)3]
Mr654.43563.29
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)298298
a, b, c (Å)18.1212 (3), 18.0363 (2), 21.8937 (1)17.7536 (3), 9.3746 (1), 17.8985 (2)
β (°) 98.454 (1) 102.981 (1)
V3)7078.0 (1)2902.77 (7)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.760.91
Crystal size (mm)0.38 × 0.24 × 0.200.44 × 0.22 × 0.18
Data collection
DiffractometerSiemens CCD area-detector
diffractometer
Siemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical
(SADABS; Sheldrick, 1996)
Empirical
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.761, 0.8630.690, 0.853
No. of measured, independent and
observed [I > 2σ(I)] reflections
36773, 12367, 6929 19786, 7133, 4770
Rint0.0550.059
(sin θ/λ)max1)0.5950.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.189, 1.07 0.049, 0.155, 1.06
No. of reflections123677133
No. of parameters703307
No. of restraints33020
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.74, 0.430.88, 1.08

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), ORTEP-II (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
Sn1a—C1a2.127 (9)Sn1b—C1b2.20 (1)
Sn1a—C5a2.13 (1)Sn1b—C5b2.15 (1)
Sn1a—C9a2.08 (1)Sn1b—C9b2.14 (1)
Sn1a—O1a2.285 (4)Sn1b—O1b2.286 (5)
Sn1a—O3ai2.292 (4)Sn1b—O3bii2.292 (5)
C1a—Sn1a—C5a118.2 (4)C1b—Sn1b—C5b115.6 (5)
C1a—Sn1a—C9a117.0 (5)C1b—Sn1b—C9b119.1 (5)
C1a—Sn1a—O1a86.5 (3)C1b—Sn1b—O1b87.8 (4)
C1a—Sn1a—O3ai91.4 (3)C1b—Sn1b—O3bii88.6 (4)
C5a—Sn1a—C9a124.8 (5)C5b—Sn1b—C9b125.3 (4)
C5a—Sn1a—O1a91.6 (3)C5b—Sn1b—O1b88.3 (3)
C5a—Sn1a—O3ai94.0 (3)C5b—Sn1b—O3bii94.9 (3)
C9a—Sn1a—O1a89.8 (3)C9b—Sn1b—O1b93.8 (3)
C9a—Sn1a—O3ai86.5 (3)C9b—Sn1b—O3bii86.2 (3)
O1a—Sn1a—O3ai174.3 (2)O1b—Sn1b—O3bii176.0 (2)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.
Selected geometric parameters (Å, º) for (II) top
Sn1—C12.146 (5)Sn1—O12.275 (2)
Sn1—C52.152 (4)Sn1—O3i2.279 (2)
Sn1—C92.113 (5)
C1—Sn1—C5115.3 (2)C5—Sn1—O191.9 (1)
C1—Sn1—C9124.2 (2)C5—Sn1—O3i85.3 (1)
C1—Sn1—O187.0 (1)C9—Sn1—O192.3 (2)
C1—Sn1—O3i90.2 (2)C9—Sn1—O3i93.0 (2)
C5—Sn1—C9120.5 (2)O1—Sn1—O3i174.7 (1)
Symmetry code: (i) x1/2, y+1/2, z1/2.
 

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