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The crystal structure of the title compound, [Sn4(C4H9)8(C10H6NO4)4O2], contains centrosymmetric dimers. It contains a central Sn2O2 core with the O atoms bonded to two di­butyl­bis(N-phthaloyl­glycinato)­tin units. The Sn atoms of the core are six-coordinate in a skew trapezoidal bipyramidal geometry, while the exocyclic Sn atoms are essentially five-coordinate in a distorted trigonal geometry. The Sn-C distances lie in a narrow range of 2.120 (5)-2.138 (4) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199013591/bk1497sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199013591/bk1497Isup2.hkl
Contains datablock I

CCDC reference: 142727

Comment top

It has been reported that diorganotin complexes containing carboxylic acids, amino acids, purines, pyrimidines and peptides exhibit maximum antitumour activity, low mammalian toxicity and less nephrotoxicity than cis-platin (Sandhu et al., 1992; Danish et al., 1996; Gielen et al., 1992). The structural chemistry of organotin complexes of amino acids protected as carboxylates has afforded a great diversity of structural variation in recent years and complexes with a coordination number higher than four are being extensively studied (Tiekink, 1994; Mehring et al., 1998; Parvez et al., 1999). A number of crystal structures of organotin complexes containing the ligand N-phthaloylglycinate, a protected amino acid, and showing interesting features have been reported. For example, in triphenyltin N-phthaloylglycinate, six molecules were bridged via carboxylate groups to form a cyclic hexamer (Ng et al., 1990). In the tricyclohexyltin analog, the molecules were linked into a helical chain through an amido-O atom (Ng & Kumar Das, 1997). This protected amino acid, when condensed with (p-chlorophenyl)diphenyl hydroxide, yielded the corresponding aqua carboxylate, wherein the coordinated water molecules had linked adjacent molecules into sheets through hydrogen-bonding (Lo et al., 1997). It has been reported that dicarboxylato tetraorgano distannoxanes are often formed when diorganotin oxides are reacted with carboxylic acids and are the products of incomplete hydrolysis (Ng & Kumar Das, 1995a). In this paper we report the crystal structure of such a product, the title compound, (I).

The structure of (I) is presented in Fig. 1. It is composed of a centrosymmetric dimer, with Sn1/O1/Sn2/O6 and Sn1i/O1i/Sn2i/O6i rings flanking an Sn1/O1/Sn1i/O1i core ring on opposite sides (symmetry code: (i) 2 − x, −y, 1 − z). Similar structural units have already been reported (Ng, et al., 1991, 1994; Ng, 1998). The endocyclic Sn atoms of the Sn2O2 core are six-coordinate in a C2SnO4 skew-trapezoidal bipyramidal geometry, wherein Sn1 is coordinated to two bridging O atoms, two N-phthaloylglycinato anions and two α-C atoms of the n-butyl groups. The endocyclic Sn—O distances in the Sn2O2 core, 2.043 (3) and 2.178 (3) Å, are similar to the corresponding distances found in tetrabutyl bis(N,N-diethyl-thiocarbamoylthio) distannoxane dimer (Ng & Kumar Das, 1995a), bis[1,1,3,3-tetrabutyl-1,3-bis(picolinato N-oxide]distannoxane hydrate (Ng, 1998) and the isomeric triphenyltin 2-, 3- and 4-pyridinecarboxylate N-oxides (Ng & Kumar Das, 1995b). The exocyclic distances Sn1—O2 and Sn1—O6 comprise a strong and a relatively weak Sn···O interaction [2.304 (3) and 2.746 (3) Å, respectively] and are similar to those observed in the above mentioned complexes. The exocyclic Sn2 is essentially five-coordinate in a distorted trigonal geometry, the C—Sn—C angle being 135.34 (19)°.

The Sn—C distances, which are almost identical, lie within the narrow range of 2.120 (5)–2.138 (4) Å and are in agreement with the values reported for related structures. The molecular dimensions in the ligand, N-phthaloylglycinate, are normal and agree with the corresponding molecular dimensions reported in the structure of 2-phthalimidoethanoic acid monohydrate (Feeder & Jones, 1994).

Experimental top

The title compound was prepared by treating equimolar quantities of phthaloylglycine and dibutyltin oxide in toluene/ethanol (3:1) under azeotropic reflux conditions for 4 h. The solid thus obtained was recrystallized from ethanol.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with the atomic numbering scheme. Displacement ellipsoids have been plotted at the 30% probability level and H atoms have been omitted for clarity. Atom C18', representing the smaller fraction of the disordered methyl atom C18, has been ignored [symmetry code: (i) 2 − x, −y, 1 − z.
octabutyl-1k2C,2k2C,3k2C,4k2C-bis-m3oxo- 1:2:3k3O;1:3:4k3O-tetrakis(m-phthalimidoacetato)- 1:2k2O;2:3k2O:O';3:4k2O;1:4k2O:O'-tetratin(IV) top
Crystal data top
[Sn4(C4H9)8(C10H6NO4)4O2]Z = 1
Mr = 1780.28F(000) = 1800
Triclinic, P1Dx = 1.566 Mg m3
a = 13.344 (5) ÅMo Kα radiation, λ = 0.7107 Å
b = 14.393 (4) ÅCell parameters from 25 reflections
c = 11.683 (2) Åθ = 9.0–15.0°
α = 93.51 (3)°µ = 1.38 mm1
β = 110.00 (2)°T = 170 K
γ = 64.19 (2)°Prism, colourless
V = 1888.0 (10) Å30.48 × 0.26 × 0.21 mm
Data collection top
Rigaku AFC-6S
diffractometer
5278 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.027
Graphite monochromatorθmax = 27.6°, θmin = 2.1°
ω–2θ scansh = 017
Absorption correction: ψ scans (north et al., 1968)
?
k = 1618
Tmin = 0.70, Tmax = 0.75l = 1514
9112 measured reflections3 standard reflections every 200 reflections
8728 independent reflections intensity decay: 1.1%
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.02Calculated w = 1/[σ2(Fo2) + (0.0115P)2 + 2.325P]
where P = (Fo2 + 2Fc2)/3
8728 reflections(Δ/σ)max = 0.002
447 parametersΔρmax = 0.93 e Å3
2 restraintsΔρmin = 0.74 e Å3
Crystal data top
[Sn4(C4H9)8(C10H6NO4)4O2]γ = 64.19 (2)°
Mr = 1780.28V = 1888.0 (10) Å3
Triclinic, P1Z = 1
a = 13.344 (5) ÅMo Kα radiation
b = 14.393 (4) ŵ = 1.38 mm1
c = 11.683 (2) ÅT = 170 K
α = 93.51 (3)°0.48 × 0.26 × 0.21 mm
β = 110.00 (2)°
Data collection top
Rigaku AFC-6S
diffractometer
5278 reflections with I > 2σ(I)
Absorption correction: ψ scans (north et al., 1968)
?
Rint = 0.027
Tmin = 0.70, Tmax = 0.753 standard reflections every 200 reflections
9112 measured reflections intensity decay: 1.1%
8728 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0322 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.93 e Å3
8728 reflectionsΔρmin = 0.74 e Å3
447 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.94759 (3)0.05335 (2)0.35757 (3)0.02554 (8)
Sn20.91653 (3)0.24001 (2)0.58348 (3)0.02609 (8)
O10.9698 (2)0.0895 (2)0.5458 (2)0.0254 (6)
O20.9544 (3)0.0213 (3)0.1785 (3)0.0416 (9)
O30.9887 (3)0.1862 (2)0.2085 (3)0.0373 (8)
O41.0688 (3)0.2861 (3)0.0803 (3)0.0464 (9)
O50.7225 (3)0.1540 (3)0.0022 (4)0.0590 (11)
O60.8493 (3)0.2611 (2)0.3860 (3)0.0306 (7)
O70.7614 (3)0.4291 (2)0.4112 (3)0.0361 (8)
O80.4710 (3)0.4576 (3)0.1640 (4)0.0536 (10)
O90.7490 (3)0.5585 (3)0.1550 (3)0.0498 (10)
N10.8978 (4)0.1982 (3)0.0366 (3)0.0358 (9)
N20.6308 (3)0.4823 (3)0.1645 (3)0.0338 (9)
C10.9565 (4)0.1065 (4)0.1427 (4)0.0314 (11)
C20.9137 (5)0.1071 (4)0.0049 (4)0.0397 (12)
H2A0.83870.04610.03060.072 (3)*
H2B0.97070.10210.02540.072 (3)*
C30.9771 (4)0.2808 (4)0.0762 (4)0.0317 (11)
C40.9253 (4)0.3557 (4)0.1083 (4)0.0327 (10)
C50.9661 (4)0.4510 (4)0.1543 (4)0.0408 (12)
H51.03560.47740.17250.072 (3)*
C60.8987 (5)0.5045 (4)0.1719 (5)0.0481 (14)
H60.92430.56880.20190.072 (3)*
C70.7949 (5)0.4666 (4)0.1468 (5)0.0481 (14)
H70.75260.50570.15960.072 (3)*
C80.7533 (4)0.3709 (4)0.1024 (4)0.0418 (12)
H80.68300.34430.08590.072 (3)*
C90.8194 (4)0.3166 (4)0.0839 (4)0.0338 (11)
C100.8015 (4)0.2145 (4)0.0353 (4)0.0398 (12)
C111.0824 (4)0.0887 (3)0.3441 (4)0.0352 (11)
H11A1.05180.13040.26700.072 (3)*
H11B1.10030.13020.40940.072 (3)*
C121.1969 (4)0.0058 (4)0.3515 (5)0.0413 (12)
H12A1.18110.04360.28120.072 (3)*
H12B1.22370.05120.42460.072 (3)*
C131.2955 (5)0.0219 (5)0.3545 (6)0.0587 (16)
H13A1.27050.06410.27930.072 (3)*
H13B1.30850.06290.42210.072 (3)*
C141.4115 (6)0.0730 (5)0.3687 (7)0.083 (2)
H14A1.47140.05150.37340.072 (3)*
H14B1.40050.11170.29950.072 (3)*
H14C1.43610.11570.44230.072 (3)*
C150.7621 (4)0.0991 (4)0.2888 (4)0.0364 (11)
H15A0.72760.14370.34430.072 (3)*
H15B0.72810.14020.21050.072 (3)*
C160.7249 (5)0.0119 (4)0.2713 (5)0.0477 (14)
H16A0.75740.02900.34940.072 (3)*
H16B0.75890.03300.21570.072 (3)*
C170.5915 (5)0.0493 (5)0.2212 (6)0.0597 (17)
H17A0.56240.08330.13950.072 (3)*
H17B0.57730.01180.21210.072 (3)*
C180.5183 (8)0.1176 (8)0.2847 (10)0.068 (3)0.603 (7)
H18A0.43790.12750.24450.072 (3)*0.603 (7)
H18B0.52080.18330.28460.072 (3)*0.603 (7)
H18C0.54700.08800.36760.072 (3)*0.603 (7)
C18'0.5397 (13)0.0238 (10)0.1779 (15)0.068 (3)0.397 (7)
H18D0.45470.01260.15410.072 (3)*0.397 (7)
H18E0.57010.07760.24250.072 (3)*0.397 (7)
H18F0.56040.05400.10880.072 (3)*0.397 (7)
C190.7794 (4)0.3595 (3)0.3447 (4)0.0268 (9)
C200.7220 (4)0.3768 (3)0.2062 (4)0.0355 (11)
H20A0.78250.36200.17050.072 (3)*
H20B0.68710.32910.17830.072 (3)*
C210.5119 (4)0.5140 (4)0.1502 (4)0.0346 (11)
C220.4516 (4)0.6287 (4)0.1147 (4)0.0355 (11)
C230.3341 (5)0.6978 (4)0.0856 (5)0.0461 (13)
H230.27770.67680.08680.072 (3)*
C240.3033 (5)0.8003 (5)0.0543 (5)0.0569 (16)
H240.22450.84920.03490.072 (3)*
C250.3859 (5)0.8322 (4)0.0509 (5)0.0543 (16)
H250.36210.90180.02950.072 (3)*
C260.5048 (5)0.7612 (4)0.0793 (5)0.0506 (15)
H260.56110.78190.07670.072 (3)*
C270.5362 (4)0.6580 (4)0.1118 (4)0.0360 (11)
C280.6536 (4)0.5651 (4)0.1452 (4)0.0359 (11)
C290.7561 (4)0.2969 (4)0.6231 (4)0.0337 (11)
H29A0.76820.24920.68700.072 (3)*
H29B0.74340.36290.65630.072 (3)*
C300.6425 (4)0.3125 (4)0.5176 (4)0.0379 (12)
H30A0.65140.24580.48840.072 (3)*
H30B0.63210.35660.45080.072 (3)*
C310.5310 (4)0.3609 (4)0.5518 (5)0.0419 (12)
H31A0.53820.31450.61410.072 (3)*
H31B0.52440.42550.58620.072 (3)*
C320.4189 (5)0.3822 (5)0.4423 (5)0.0556 (16)
H32A0.35060.41790.46620.072 (3)*
H32B0.42120.31770.41330.072 (3)*
H32C0.41410.42440.37830.072 (3)*
C331.0537 (5)0.2873 (4)0.6139 (5)0.0411 (12)
H33A1.04910.33380.67760.072 (3)*
H33B1.12920.22610.64650.072 (3)*
C341.0572 (5)0.3400 (4)0.5082 (5)0.0499 (14)
H34A0.98380.40330.47660.072 (3)*
H34B1.06150.29480.44320.072 (3)*
C351.1615 (5)0.3667 (5)0.5433 (6)0.0598 (17)
H35A1.15410.40560.47350.072 (3)*
H35B1.15740.41130.60890.072 (3)*
C361.2790 (6)0.2758 (6)0.5833 (8)0.106 (3)
H36A1.34020.29870.60960.072 (3)*
H36B1.28730.23460.51630.072 (3)*
H36C1.28600.23480.65000.072 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02915 (19)0.02383 (18)0.01993 (16)0.00987 (14)0.00648 (14)0.00060 (12)
Sn20.02808 (18)0.02088 (17)0.02653 (17)0.00905 (14)0.00917 (14)0.00513 (13)
O10.0280 (16)0.0200 (15)0.0229 (15)0.0067 (13)0.0080 (13)0.0023 (12)
O20.064 (2)0.036 (2)0.0293 (18)0.0248 (18)0.0191 (17)0.0125 (15)
O30.047 (2)0.0347 (19)0.0232 (16)0.0166 (16)0.0056 (15)0.0023 (14)
O40.042 (2)0.050 (2)0.056 (2)0.0230 (19)0.0264 (19)0.0170 (18)
O50.039 (2)0.066 (3)0.058 (3)0.009 (2)0.023 (2)0.024 (2)
O60.0332 (18)0.0251 (16)0.0260 (16)0.0077 (14)0.0081 (14)0.0006 (13)
O70.043 (2)0.0253 (17)0.0365 (18)0.0120 (15)0.0145 (16)0.0034 (14)
O80.048 (2)0.051 (2)0.063 (3)0.022 (2)0.019 (2)0.002 (2)
O90.039 (2)0.050 (2)0.061 (3)0.0157 (18)0.0213 (19)0.0044 (19)
N10.038 (2)0.037 (2)0.027 (2)0.0126 (19)0.0098 (18)0.0093 (17)
N20.031 (2)0.030 (2)0.031 (2)0.0070 (18)0.0069 (18)0.0091 (17)
C10.026 (2)0.042 (3)0.021 (2)0.012 (2)0.0071 (19)0.005 (2)
C20.052 (3)0.032 (3)0.023 (2)0.014 (2)0.007 (2)0.005 (2)
C30.036 (3)0.030 (3)0.023 (2)0.011 (2)0.009 (2)0.0037 (19)
C40.033 (3)0.036 (3)0.027 (2)0.014 (2)0.010 (2)0.007 (2)
C50.036 (3)0.038 (3)0.041 (3)0.011 (2)0.012 (2)0.010 (2)
C60.057 (4)0.043 (3)0.047 (3)0.027 (3)0.018 (3)0.018 (3)
C70.055 (4)0.049 (3)0.045 (3)0.031 (3)0.013 (3)0.008 (3)
C80.029 (3)0.056 (3)0.035 (3)0.018 (3)0.006 (2)0.004 (2)
C90.029 (3)0.039 (3)0.028 (2)0.011 (2)0.007 (2)0.003 (2)
C100.033 (3)0.048 (3)0.025 (2)0.011 (2)0.005 (2)0.007 (2)
C110.042 (3)0.027 (2)0.041 (3)0.016 (2)0.018 (2)0.002 (2)
C120.042 (3)0.032 (3)0.055 (3)0.017 (2)0.023 (3)0.005 (2)
C130.043 (3)0.058 (4)0.073 (4)0.017 (3)0.023 (3)0.001 (3)
C140.056 (4)0.086 (6)0.109 (6)0.030 (4)0.033 (4)0.009 (5)
C150.027 (2)0.038 (3)0.033 (3)0.009 (2)0.004 (2)0.000 (2)
C160.036 (3)0.055 (4)0.053 (3)0.024 (3)0.014 (3)0.016 (3)
C170.039 (3)0.078 (5)0.058 (4)0.030 (3)0.003 (3)0.011 (3)
C180.039 (5)0.067 (6)0.087 (7)0.024 (5)0.012 (5)0.012 (5)
C18'0.039 (5)0.067 (6)0.087 (7)0.024 (5)0.012 (5)0.012 (5)
C190.027 (2)0.020 (2)0.031 (2)0.0077 (18)0.011 (2)0.0006 (18)
C200.042 (3)0.026 (2)0.030 (2)0.007 (2)0.013 (2)0.0037 (19)
C210.030 (3)0.039 (3)0.026 (2)0.009 (2)0.007 (2)0.001 (2)
C220.033 (3)0.040 (3)0.024 (2)0.009 (2)0.007 (2)0.000 (2)
C230.038 (3)0.050 (3)0.036 (3)0.010 (3)0.009 (2)0.003 (2)
C240.039 (3)0.047 (4)0.050 (4)0.005 (3)0.008 (3)0.005 (3)
C250.060 (4)0.030 (3)0.049 (3)0.000 (3)0.018 (3)0.004 (2)
C260.059 (4)0.044 (3)0.043 (3)0.015 (3)0.021 (3)0.001 (3)
C270.032 (3)0.034 (3)0.029 (2)0.006 (2)0.005 (2)0.003 (2)
C280.035 (3)0.036 (3)0.032 (3)0.011 (2)0.011 (2)0.005 (2)
C290.037 (3)0.033 (3)0.032 (3)0.013 (2)0.017 (2)0.007 (2)
C300.033 (3)0.044 (3)0.035 (3)0.013 (2)0.015 (2)0.007 (2)
C310.034 (3)0.045 (3)0.051 (3)0.017 (2)0.021 (3)0.011 (2)
C320.036 (3)0.063 (4)0.061 (4)0.016 (3)0.016 (3)0.001 (3)
C330.042 (3)0.043 (3)0.046 (3)0.027 (3)0.014 (2)0.009 (2)
C340.054 (4)0.039 (3)0.064 (4)0.025 (3)0.021 (3)0.001 (3)
C350.059 (4)0.057 (4)0.075 (4)0.039 (3)0.018 (3)0.001 (3)
C360.059 (5)0.098 (7)0.170 (9)0.033 (5)0.049 (6)0.020 (6)
Geometric parameters (Å, º) top
Sn1—C112.125 (5)C4—C51.388 (6)
Sn1—C152.120 (5)C4—C91.400 (6)
Sn1—O1i2.043 (3)C5—C61.380 (7)
Sn1—O12.178 (3)C6—C71.379 (7)
Sn1—O22.304 (3)C7—C81.385 (7)
Sn1—O62.746 (3)C8—C91.372 (7)
Sn2—C332.133 (5)C9—C101.491 (7)
Sn2—C292.138 (4)C11—C121.519 (6)
Sn2—O12.037 (3)C12—C131.521 (7)
Sn2—O3i2.320 (3)C13—C141.516 (8)
Sn2—O62.157 (3)C15—C161.518 (7)
O1—Sn1i2.043 (3)C16—C171.515 (7)
O2—C11.263 (5)C17—C181.428 (8)
O3—C11.243 (5)C17—C18'1.473 (9)
O3—Sn2i2.320 (3)C19—C201.517 (6)
O4—C31.211 (5)C21—C221.498 (7)
O5—C101.208 (6)C22—C231.372 (7)
O6—C191.317 (5)C22—C271.376 (7)
O7—C191.220 (5)C23—C241.383 (8)
O8—C211.203 (6)C24—C251.379 (8)
O9—C281.200 (5)C25—C261.393 (7)
N1—C31.385 (6)C26—C271.395 (7)
N1—C101.409 (6)C27—C281.489 (6)
N1—C21.446 (6)C29—C301.525 (6)
N2—C211.397 (6)C30—C311.527 (6)
N2—C281.400 (6)C31—C321.519 (7)
N2—C201.450 (5)C33—C341.513 (7)
C1—C21.514 (6)C34—C351.520 (7)
C3—C41.483 (6)C35—C361.475 (8)
O1i—Sn1—C15108.09 (15)C9—C4—C3109.0 (4)
O1i—Sn1—C11107.38 (15)C6—C5—C4116.7 (5)
C15—Sn1—C11143.71 (18)C5—C6—C7122.8 (5)
O1i—Sn1—O176.73 (12)C6—C7—C8120.4 (5)
C15—Sn1—O199.41 (15)C9—C8—C7117.6 (5)
C11—Sn1—O195.88 (15)C8—C9—C4121.8 (5)
O1i—Sn1—O291.03 (11)C8—C9—C10131.0 (5)
C15—Sn1—O287.44 (16)C4—C9—C10107.1 (4)
C11—Sn1—O284.49 (16)O5—C10—N1124.2 (5)
O1—Sn1—O2167.32 (11)O5—C10—C9130.0 (5)
O1—Sn1—O665.00 (11)N1—C10—C9105.8 (4)
O1i—Sn1—O6141.54 (11)C12—C11—Sn1114.4 (3)
O2—Sn1—O6127.37 (12)C11—C12—C13113.0 (4)
C11—Sn1—O681.08 (16)C14—C13—C12112.7 (5)
C15—Sn1—O676.02 (16)C16—C15—Sn1116.1 (3)
O1—Sn2—C33111.46 (16)C15—C16—C17113.7 (5)
O1—Sn2—C29111.28 (15)C18—C17—C18'103.7 (9)
C33—Sn2—C29135.34 (19)C18—C17—C16120.9 (6)
O1—Sn2—O679.67 (11)C18'—C17—C16120.9 (8)
C33—Sn2—O697.95 (16)O7—C19—O6123.4 (4)
C29—Sn2—O6101.78 (15)O7—C19—C20123.7 (4)
O1—Sn2—O3i90.29 (11)O6—C19—C20113.0 (4)
C33—Sn2—O3i82.44 (16)N2—C20—C19111.8 (4)
C29—Sn2—O3i84.98 (15)O8—C21—N2125.0 (5)
O6—Sn2—O3i169.40 (11)O8—C21—C22129.6 (5)
Sn2—O1—Sn1i137.12 (14)N2—C21—C22105.4 (4)
Sn2—O1—Sn1119.55 (13)C23—C22—C27122.5 (5)
Sn1i—O1—Sn1103.27 (12)C23—C22—C21129.7 (5)
C1—O2—Sn1133.0 (3)C27—C22—C21107.8 (4)
C1—O3—Sn2i135.1 (3)C22—C23—C24116.9 (5)
C19—O6—Sn2111.2 (3)C25—C24—C23122.0 (5)
C3—N1—C10112.3 (4)C24—C25—C26120.6 (5)
C3—N1—C2124.5 (4)C25—C26—C27117.5 (6)
C10—N1—C2123.1 (4)C22—C27—C26120.5 (5)
C21—N2—C28112.6 (4)C22—C27—C28109.3 (4)
C21—N2—C20123.3 (4)C26—C27—C28130.2 (5)
C28—N2—C20123.9 (4)O9—C28—N2125.4 (5)
O3—C1—O2126.6 (4)O9—C28—C27129.7 (5)
O3—C1—C2119.1 (4)N2—C28—C27104.9 (4)
O2—C1—C2114.3 (4)C30—C29—Sn2117.4 (3)
N1—C2—C1114.2 (4)C29—C30—C31113.8 (4)
O4—C3—N1124.2 (5)C32—C31—C30112.2 (4)
O4—C3—C4130.1 (4)C34—C33—Sn2119.4 (4)
N1—C3—C4105.7 (4)C33—C34—C35113.3 (5)
C5—C4—C9120.6 (5)C36—C35—C34114.2 (5)
C5—C4—C3130.5 (4)
C33—Sn2—O1—Sn1i89.3 (3)O1i—Sn1—C11—C1226.2 (4)
C29—Sn2—O1—Sn1i77.4 (3)C15—Sn1—C11—C12141.2 (4)
O6—Sn2—O1—Sn1i176.1 (2)O1—Sn1—C11—C12104.1 (4)
O3i—Sn2—O1—Sn1i7.3 (2)O2—Sn1—C11—C1263.1 (4)
C33—Sn2—O1—Sn187.4 (2)Sn1—C11—C12—C13174.2 (4)
C29—Sn2—O1—Sn1105.90 (18)C11—C12—C13—C14176.9 (5)
O6—Sn2—O1—Sn17.17 (14)O1i—Sn1—C15—C1625.2 (4)
O3i—Sn2—O1—Sn1169.38 (16)C11—Sn1—C15—C16142.2 (4)
O1i—Sn1—O1—Sn2177.7 (2)O1—Sn1—C15—C16104.2 (4)
C15—Sn1—O1—Sn275.79 (19)O2—Sn1—C15—C1665.1 (4)
C11—Sn1—O1—Sn271.18 (19)Sn1—C15—C16—C17179.6 (4)
O2—Sn1—O1—Sn2162.2 (5)C15—C16—C17—C1858.1 (9)
O1i—Sn1—O1—Sn1i0.001 (1)C15—C16—C17—C18'169.0 (9)
C15—Sn1—O1—Sn1i106.52 (17)Sn2—O6—C19—O73.7 (5)
C11—Sn1—O1—Sn1i106.51 (16)Sn2—O6—C19—C20175.2 (3)
O2—Sn1—O1—Sn1i15.5 (6)C21—N2—C20—C1988.9 (5)
O1i—Sn1—O2—C127.4 (4)C28—N2—C20—C1984.9 (5)
C15—Sn1—O2—C180.7 (4)O7—C19—C20—N28.7 (7)
C11—Sn1—O2—C1134.8 (5)O6—C19—C20—N2170.3 (4)
O1—Sn1—O2—C142.5 (8)C28—N2—C21—O8178.7 (5)
O1—Sn2—O6—C19170.2 (3)C20—N2—C21—O84.3 (8)
C33—Sn2—O6—C1979.3 (3)C28—N2—C21—C221.6 (5)
C29—Sn2—O6—C1960.4 (3)C20—N2—C21—C22176.1 (4)
O3i—Sn2—O6—C19170.7 (6)O8—C21—C22—C232.1 (9)
Sn2i—O3—C1—O210.4 (8)N2—C21—C22—C23177.5 (5)
Sn2i—O3—C1—C2170.1 (3)O8—C21—C22—C27179.6 (5)
Sn1—O2—C1—O322.0 (8)N2—C21—C22—C270.8 (5)
Sn1—O2—C1—C2157.5 (3)C27—C22—C23—C241.0 (8)
C3—N1—C2—C1102.1 (5)C21—C22—C23—C24179.1 (5)
C10—N1—C2—C174.7 (6)C22—C23—C24—C250.7 (8)
O3—C1—C2—N19.1 (7)C23—C24—C25—C260.0 (9)
O2—C1—C2—N1170.5 (4)C24—C25—C26—C270.5 (8)
C10—N1—C3—O4177.0 (5)C23—C22—C27—C260.5 (8)
C2—N1—C3—O40.1 (7)C21—C22—C27—C26179.0 (4)
C10—N1—C3—C42.5 (5)C23—C22—C27—C28178.7 (4)
C2—N1—C3—C4179.5 (4)C21—C22—C27—C280.2 (5)
O4—C3—C4—C51.6 (9)C25—C26—C27—C220.3 (8)
N1—C3—C4—C5179.0 (5)C25—C26—C27—C28179.2 (5)
O4—C3—C4—C9177.8 (5)C21—N2—C28—O9178.1 (5)
N1—C3—C4—C91.6 (5)C20—N2—C28—O93.6 (8)
C9—C4—C5—C61.2 (7)C21—N2—C28—C271.7 (5)
C3—C4—C5—C6178.2 (5)C20—N2—C28—C27176.2 (4)
C4—C5—C6—C70.6 (8)C22—C27—C28—O9178.6 (5)
C5—C6—C7—C80.3 (9)C26—C27—C28—O92.3 (9)
C6—C7—C8—C90.6 (8)C22—C27—C28—N21.1 (5)
C7—C8—C9—C40.0 (7)C26—C27—C28—N2177.9 (5)
C7—C8—C9—C10178.4 (5)O1—Sn2—C29—C3069.2 (4)
C5—C4—C9—C81.0 (7)C33—Sn2—C29—C30128.5 (4)
C3—C4—C9—C8178.6 (4)O6—Sn2—C29—C3014.2 (4)
C5—C4—C9—C10179.7 (4)O3i—Sn2—C29—C30157.6 (4)
C3—C4—C9—C100.2 (5)Sn2—C29—C30—C31175.6 (3)
C3—N1—C10—O5178.6 (5)C29—C30—C31—C32175.9 (4)
C2—N1—C10—O51.5 (7)O1—Sn2—C33—C3493.7 (4)
C3—N1—C10—C92.4 (5)C29—Sn2—C33—C34104.1 (4)
C2—N1—C10—C9179.5 (4)O6—Sn2—C33—C3411.7 (4)
C8—C9—C10—O51.2 (9)O3i—Sn2—C33—C34179.0 (4)
C4—C9—C10—O5179.8 (5)Sn2—C33—C34—C35178.6 (4)
C8—C9—C10—N1179.8 (5)C33—C34—C35—C3663.5 (8)
C4—C9—C10—N11.3 (5)
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formula[Sn4(C4H9)8(C10H6NO4)4O2]
Mr1780.28
Crystal system, space groupTriclinic, P1
Temperature (K)170
a, b, c (Å)13.344 (5), 14.393 (4), 11.683 (2)
α, β, γ (°)93.51 (3), 110.00 (2), 64.19 (2)
V3)1888.0 (10)
Z1
Radiation typeMo Kα
µ (mm1)1.38
Crystal size (mm)0.48 × 0.26 × 0.21
Data collection
DiffractometerRigaku AFC-6S
diffractometer
Absorption correctionψ scans (North et al., 1968)
Tmin, Tmax0.70, 0.75
No. of measured, independent and
observed [I > 2σ(I)] reflections
9112, 8728, 5278
Rint0.027
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.082, 1.02
No. of reflections8728
No. of parameters447
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.93, 0.74

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), TEXSAN, SHELXL97.

Selected geometric parameters (Å, º) top
Sn1—C112.125 (5)Sn2—C332.133 (5)
Sn1—C152.120 (5)Sn2—C292.138 (4)
Sn1—O1i2.043 (3)Sn2—O12.037 (3)
Sn1—O12.178 (3)Sn2—O3i2.320 (3)
Sn1—O22.304 (3)Sn2—O62.157 (3)
O1i—Sn1—C15108.09 (15)O1—Sn2—C33111.46 (16)
O1i—Sn1—C11107.38 (15)O1—Sn2—C29111.28 (15)
C15—Sn1—C11143.71 (18)C33—Sn2—C29135.34 (19)
O1i—Sn1—O176.73 (12)O1—Sn2—O679.67 (11)
C15—Sn1—O199.41 (15)C33—Sn2—O697.95 (16)
C11—Sn1—O195.88 (15)C29—Sn2—O6101.78 (15)
O1i—Sn1—O291.03 (11)O1—Sn2—O3i90.29 (11)
C15—Sn1—O287.44 (16)C33—Sn2—O3i82.44 (16)
C11—Sn1—O284.49 (16)C29—Sn2—O3i84.98 (15)
O1—Sn1—O2167.32 (11)O6—Sn2—O3i169.40 (11)
Symmetry code: (i) x+2, y, z+1.
 

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