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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1406–m1407.
Published online 2010 October 13. doi:  10.1107/S1600536810040146
PMCID: PMC3009280

Bis(μ2-4-amino-3-nitro­benzoato)bis­(4-amino-3-nitro­benzoato)octa­butyldi-μ3-oxido-tetra­tin(IV)

Abstract

The tetranuclear molecules of the title compound, [Sn4(C4H9)8(C7H5N2O4)4O2], reside on a crystallographic inversion center. Both the two independent Sn atoms are five-coordinate, with distorted trigonal–bipyramidal geometries. One Sn atom is coordinated by two O atoms of the carboxyl­ate anions, one bridging O atom and two butyl groups and the other Sn atom is coordinated by an O atom of the carboxyl­ate anion, two bridging O atoms and two butyl groups. All the butyl groups are equatorial with respect to the SnO3 trigonal plane. The mol­ecular structure is stabilized by intra­molecular N—H(...)O hydrogen bonds. In the crystal, pairs of inter­molecular bifurcated acceptor N—H(...)O and C—H(...)O hydrogen bonds link the mol­ecules into chains along [10An external file that holds a picture, illustration, etc.
Object name is e-66-m1406-efi1.jpg]. Weak inter­molecular C—H(...)π and π–π inter­actions [centroid–centroid distance = 3.713 (2) Å] are also observed.

Related literature

For general background to and applications of the title complex, see: Khoo & Hazell (1999 [triangle]); Parvez et al. (2004 [triangle]); Li et al. (2006 [triangle]); Win et al. (2008a [triangle],b [triangle]). For closely related structures, see: Khoo & Hazell (1999 [triangle]); Parvez et al. (2004 [triangle]); Li et al. (2006 [triangle]); Win et al. (2008b [triangle]). For graph-set motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1406-scheme1.jpg

Experimental

Crystal data

  • [Sn4(C4H9)8(C7H5N2O4)4O2]
  • M r = 1688.18
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1406-efi3.jpg
  • a = 11.9585 (9) Å
  • b = 13.0679 (10) Å
  • c = 13.1897 (10) Å
  • α = 76.256 (2)°
  • β = 67.445 (2)°
  • γ = 66.108 (2)°
  • V = 1732.1 (2) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.50 mm−1
  • T = 100 K
  • 0.20 × 0.15 × 0.06 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.758, T max = 0.912
  • 32184 measured reflections
  • 11359 independent reflections
  • 8603 reflections with I > 2σ(I)
  • R int = 0.055

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.116
  • S = 1.04
  • 11359 reflections
  • 410 parameters
  • H-atom parameters constrained
  • Δρmax = 1.26 e Å−3
  • Δρmin = −1.18 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040146/fj2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040146/fj2350Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors would like to thank Universiti Tunku Abdul Rahman (UTAR) for the UTAR Research Fund (Vote No. 6200/Y02) and Universiti Sains Malaysia (USM) for financial support as well as technical assistance and facilities. HKF and JHG also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

In general, there are many well-documented structures on complexes isolated from 1:1 molar ratio reaction between diorganotin(IV) with the respective organic acids (Khoo & Hazell, 1999; Parvez et al., 2004; Li et al., 2006; Win et al., 2008a,b). This dimeric structure is known as organodistannoxane dimer with the core geometry consisting of a centrosymmetric planar Sn2O2 group (Win et al., 2008a,b). The centrosymmetric planar Sn2O2 group is bonded to the exo- and endocyclic tin(IV) atom moiety via the bridging oxygen atoms so that the oxygen atoms are tri-coordinated (Khoo & Hazell, 1999; Parvez et al., 2004; Li et al., 2006). In this study, the crystal structure of the title complex is similar to bis(2,3-dibromopropionato)tetrabutyldistannoxane(IV) dimer and consists of a centrosymmetric planar Sn2O2 group (Win et al., 2008b). The only exception is 4-amino-3-nitrobenzoic acid is utilized in the reaction to obtain the title complex.

The asymmetric unit of the title complex (Fig. 1) lies on a crystallographic inversion center and comprises of one-half molecule, with the other half of the molecule is generated by symmetry code -x, -y+1, -z. The Sn1 atom is five-coordinated by two butyl groups in equatorial position, an O atom of the monodentate carboxylate anion, an O atom of the bridging carboxylate atom and one bridging O atom in a distorted trigonal bipiramidal geometry. The Sn2 atom also has a distorted trigonal bipiramidal geometry, being coordinated by two butyl groups in equatorial position, one bridging carboxylate O atom and two bridging O atoms. Intramolecular N1—H2N1···O1 and N3—H2N3···O5 hydrogen bonds (Table 1) form two different six-membered rings, generating S(6) ring motifs (Bernstein et al., 1995) which help to stabilize the molecular structure. All geometric parameters are consistent to those observed in closely related structures (Khoo & Hazell, 1999; Parvez et al., 2004; Li et al., 2006; Win et al., 2008b).

In the crystal structure, pairs of intermolecular bifurcated acceptor N3—H1N3···O4 and C17—H17A···O4 hydrogen bonds (Table 1) link adjacent molecules into one-dimensional chains incorporating R21(6) hydrogen bond ring motifs along the [101] direction (Bernstein et al., 1995, Fig. 2). Further stabilization of the crystal structure is provided by weak intermolecular C30—H30A···Cg1 interactions (Table 1) as well as Cg1···Cg2 aromatic stacking interactions where Cg1 and Cg 2 are the centroids of the C16-C21 and C1-C6 benzene rings.

Experimental

The title complex was obtained by heating under reflux in a 1:1 molar mixture of dibutyltin(IV) oxide (0.50 g, 2 mmol) and 4-amino-3-nitrobenzoic acid (0.36 g, 2 mmol) in methanol (50 ml) for 4 h. Clear yellowish solution was isolated by filtration and kept in a bottle. After 12 days, yellow single crystals (0.71 g, 75.8 % yeild) were collected. M.p. 525.8–527.4 K. Analysis found for C60H92N8O18Sn4: C, 42.84; H, 5.43; N, 6.49; Sn, 28.28 %. Calculated found for C60H92N8O18Sn4: C, 42.68; H, 5.49; N, 6.64; Sn, 28.13 %.

Refinement

The amino group H atoms were located from the difference Fourier map and constrained to ride with the parent atom with Uiso = 1.2 Ueq(N). All other H atoms were placed in their calculated positions, with C—H = 0.93 – 0.97 Å, and refined using a riding model with Uiso = 1.2 or 1.5 Ueq(C). The rotating group model was used for the methyl groups. The highest residual electron density peak and the deepest hole were located at 0.72 Å from atom Sn1.

Figures

Fig. 1.
The molecular structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The suffix A corresponds to symmetry code [-x, -y+1, -z]. Intramolecular hydrogen bonds are shown as dashed lines and all C-bound ...
Fig. 2.
The crystal structure of the title complex, viewed along the b axis, showing a one-dimensional chain along the [101] direction. H atoms not involved in intermolecular hydrogen bonds (dashed lines) have been omitted for clarity.

Crystal data

[Sn4(C4H9)8(C7H5N2O4)4O2]Z = 1
Mr = 1688.18F(000) = 852
Triclinic, P1Dx = 1.618 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.9585 (9) ÅCell parameters from 5645 reflections
b = 13.0679 (10) Åθ = 3.4–33.2°
c = 13.1897 (10) ŵ = 1.50 mm1
α = 76.256 (2)°T = 100 K
β = 67.445 (2)°Block, yellow
γ = 66.108 (2)°0.20 × 0.15 × 0.06 mm
V = 1732.1 (2) Å3

Data collection

Bruker APEXII DUO CCD area-detector diffractometer11359 independent reflections
Radiation source: fine-focus sealed tube8603 reflections with I > 2σ(I)
graphiteRint = 0.055
[var phi] and ω scansθmax = 31.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −17→17
Tmin = 0.758, Tmax = 0.912k = −19→18
32184 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0611P)2] where P = (Fo2 + 2Fc2)/3
11359 reflections(Δ/σ)max = 0.001
410 parametersΔρmax = 1.25 e Å3
0 restraintsΔρmin = −1.17 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
Sn1−0.15407 (2)0.426491 (18)0.258267 (17)0.01235 (6)
Sn20.126384 (19)0.388757 (17)0.012249 (17)0.01183 (6)
O10.5285 (3)−0.1013 (3)0.4294 (3)0.0452 (9)
O20.3268 (4)−0.0394 (3)0.5298 (3)0.0469 (9)
O30.0372 (2)0.29294 (19)0.21639 (19)0.0150 (5)
O4−0.0160 (2)0.2104 (2)0.3863 (2)0.0230 (5)
O50.9029 (2)−0.0002 (2)−0.1901 (2)0.0233 (5)
O60.7210 (3)0.0470 (2)−0.0558 (2)0.0254 (6)
O70.3299 (2)0.3217 (2)−0.10236 (19)0.0183 (5)
O8−0.3316 (2)0.5805 (2)0.2675 (2)0.0187 (5)
O9−0.0734 (2)0.47928 (19)0.09963 (18)0.0133 (4)
N10.5993 (3)−0.0496 (3)0.2134 (3)0.0313 (8)
H1N10.6573−0.04350.14500.038*
H2N10.6222−0.09390.28300.038*
N20.4123 (4)−0.0430 (3)0.4400 (3)0.0315 (8)
N30.9151 (3)0.0899 (3)−0.3964 (2)0.0192 (6)
H1N30.94670.1258−0.46000.023*
H2N30.95740.0317−0.35940.023*
N40.7854 (3)0.0571 (2)−0.1543 (2)0.0173 (6)
C10.2968 (3)0.1390 (3)0.1681 (3)0.0186 (7)
H1A0.26930.17870.10840.022*
C20.4240 (3)0.0748 (3)0.1495 (3)0.0212 (7)
H2A0.48090.07180.07760.025*
C30.4715 (3)0.0126 (3)0.2369 (3)0.0213 (7)
C40.3797 (4)0.0193 (3)0.3434 (3)0.0211 (7)
C50.2486 (3)0.0864 (3)0.3609 (3)0.0182 (6)
H5A0.19020.08950.43220.022*
C60.2058 (3)0.1470 (3)0.2745 (3)0.0163 (6)
C70.0658 (3)0.2188 (3)0.2964 (3)0.0161 (6)
C8−0.2737 (3)0.3386 (3)0.2691 (3)0.0190 (7)
H8A−0.33790.34460.34200.023*
H8B−0.31950.37710.21640.023*
C9−0.2096 (4)0.2138 (3)0.2494 (3)0.0238 (7)
H9A−0.18200.17070.31180.029*
H9B−0.13340.20380.18430.029*
C10−0.3018 (4)0.1683 (3)0.2336 (4)0.0283 (8)
H10A−0.26120.08750.23130.034*
H10B−0.38020.18280.29680.034*
C11−0.3378 (6)0.2205 (5)0.1287 (4)0.0438 (12)
H11A−0.39580.18940.12400.066*
H11B−0.26110.20430.06550.066*
H11C−0.37930.30040.13070.066*
C12−0.1180 (3)0.4888 (3)0.3732 (3)0.0191 (7)
H12A−0.06760.42520.41170.023*
H12B−0.06500.53440.33210.023*
C13−0.2355 (4)0.5582 (4)0.4589 (3)0.0248 (8)
H13A−0.28620.62230.42110.030*
H13B−0.28860.51280.50100.030*
C14−0.2041 (4)0.6002 (4)0.5377 (3)0.0280 (8)
H14A−0.15210.64660.49630.034*
H14B−0.15330.53650.57580.034*
C15−0.3241 (5)0.6682 (4)0.6222 (4)0.0352 (10)
H15A−0.29920.69270.67070.053*
H15B−0.37540.62240.66440.053*
H15C−0.37370.73250.58510.053*
C160.5905 (3)0.2917 (3)−0.3655 (3)0.0166 (6)
H16A0.54650.3451−0.41070.020*
C170.7173 (3)0.2297 (3)−0.4104 (3)0.0178 (6)
H17A0.75740.2407−0.48590.021*
C180.7904 (3)0.1483 (3)−0.3449 (3)0.0152 (6)
C190.7236 (3)0.1349 (3)−0.2307 (3)0.0135 (6)
C200.5918 (3)0.1990 (3)−0.1861 (3)0.0133 (6)
H20A0.54990.1885−0.11090.016*
C210.5243 (3)0.2764 (3)−0.2514 (3)0.0136 (6)
C220.3840 (3)0.3441 (3)−0.2034 (3)0.0138 (6)
C230.0916 (4)0.2564 (3)−0.0232 (3)0.0194 (7)
H23A0.15370.1853−0.00550.023*
H23B0.00610.25700.02410.023*
C240.1005 (3)0.2635 (3)−0.1432 (3)0.0183 (6)
H24A0.03630.3332−0.16040.022*
H24B0.18500.2651−0.19080.022*
C250.0794 (4)0.1652 (3)−0.1674 (3)0.0215 (7)
H25A0.13670.0952−0.14210.026*
H25B−0.00880.1689−0.12660.026*
C260.1044 (4)0.1659 (4)−0.2894 (4)0.0301 (9)
H26A0.10040.0983−0.30200.045*
H26B0.18850.1701−0.33090.045*
H26C0.04000.2299−0.31250.045*
C270.2107 (3)0.4357 (3)0.1018 (3)0.0174 (6)
H27A0.14360.46680.16820.021*
H27B0.27370.36850.12450.021*
C280.2768 (4)0.5210 (3)0.0386 (3)0.0202 (7)
H28A0.34220.4917−0.02920.024*
H28B0.21340.59000.01890.024*
C290.3397 (3)0.5474 (3)0.1050 (3)0.0221 (7)
H29A0.39600.47730.13130.027*
H29B0.39310.59060.05670.027*
C300.2445 (4)0.6125 (4)0.2031 (3)0.0269 (8)
H30A0.29080.61940.24520.040*
H30B0.18690.57330.24870.040*
H30C0.19570.68600.17740.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01042 (10)0.01296 (11)0.01006 (10)−0.00221 (7)−0.00232 (7)0.00013 (8)
Sn20.01123 (10)0.01097 (10)0.01065 (10)−0.00180 (7)−0.00337 (7)−0.00046 (7)
O10.0303 (17)0.047 (2)0.053 (2)0.0028 (14)−0.0281 (16)−0.0003 (17)
O20.042 (2)0.059 (2)0.0247 (16)−0.0027 (16)−0.0162 (15)0.0049 (15)
O30.0112 (10)0.0149 (11)0.0138 (10)−0.0025 (8)−0.0021 (8)0.0003 (9)
O40.0167 (12)0.0256 (14)0.0165 (12)−0.0040 (9)−0.0023 (10)0.0045 (10)
O50.0134 (11)0.0237 (13)0.0247 (13)0.0002 (9)−0.0071 (10)0.0013 (10)
O60.0214 (13)0.0294 (15)0.0150 (12)−0.0009 (10)−0.0053 (10)0.0010 (10)
O70.0117 (11)0.0233 (13)0.0119 (10)−0.0004 (9)−0.0021 (9)−0.0007 (9)
O80.0135 (11)0.0199 (12)0.0174 (11)0.0010 (9)−0.0068 (9)−0.0017 (9)
O90.0116 (10)0.0127 (10)0.0117 (10)−0.0025 (8)−0.0029 (8)0.0009 (8)
N10.0133 (14)0.0299 (18)0.043 (2)−0.0003 (12)−0.0082 (14)−0.0053 (16)
N20.0276 (18)0.0309 (19)0.0340 (19)−0.0016 (13)−0.0198 (15)0.0013 (15)
N30.0104 (12)0.0188 (14)0.0184 (14)−0.0006 (10)−0.0018 (10)0.0026 (11)
N40.0149 (13)0.0170 (14)0.0190 (14)−0.0021 (10)−0.0088 (11)−0.0010 (11)
C10.0141 (15)0.0159 (15)0.0233 (17)−0.0039 (11)−0.0057 (13)−0.0005 (13)
C20.0146 (15)0.0217 (17)0.0237 (17)−0.0053 (12)−0.0027 (13)−0.0040 (14)
C30.0149 (15)0.0163 (16)0.0331 (19)−0.0041 (12)−0.0078 (14)−0.0057 (14)
C40.0245 (18)0.0179 (16)0.0251 (17)−0.0081 (13)−0.0140 (14)0.0015 (14)
C50.0148 (15)0.0182 (16)0.0206 (16)−0.0051 (11)−0.0073 (13)0.0014 (13)
C60.0118 (14)0.0142 (15)0.0217 (16)−0.0041 (11)−0.0051 (12)−0.0011 (12)
C70.0144 (14)0.0132 (15)0.0188 (15)−0.0019 (11)−0.0089 (12)0.0025 (12)
C80.0149 (15)0.0174 (16)0.0218 (16)−0.0056 (11)−0.0040 (13)−0.0006 (13)
C90.0226 (17)0.0192 (17)0.0300 (19)−0.0075 (13)−0.0078 (15)−0.0041 (15)
C100.033 (2)0.0203 (18)0.034 (2)−0.0134 (15)−0.0121 (17)0.0024 (16)
C110.066 (4)0.041 (3)0.047 (3)−0.034 (3)−0.031 (3)0.004 (2)
C120.0168 (15)0.0209 (17)0.0175 (15)−0.0020 (12)−0.0073 (12)−0.0038 (13)
C130.0201 (17)0.033 (2)0.0234 (18)−0.0076 (14)−0.0060 (14)−0.0104 (16)
C140.035 (2)0.033 (2)0.0184 (17)−0.0131 (16)−0.0098 (16)−0.0030 (15)
C150.043 (3)0.035 (2)0.026 (2)−0.0060 (18)−0.0123 (19)−0.0121 (18)
C160.0147 (14)0.0166 (15)0.0148 (14)−0.0032 (11)−0.0048 (12)0.0011 (12)
C170.0132 (14)0.0192 (16)0.0143 (14)−0.0013 (11)−0.0035 (12)0.0003 (12)
C180.0118 (13)0.0148 (15)0.0173 (15)−0.0048 (11)−0.0034 (12)−0.0007 (12)
C190.0121 (13)0.0130 (14)0.0159 (14)−0.0039 (10)−0.0060 (11)−0.0007 (11)
C200.0124 (13)0.0141 (14)0.0122 (13)−0.0048 (10)−0.0026 (11)−0.0014 (11)
C210.0102 (13)0.0144 (14)0.0117 (13)−0.0014 (10)−0.0012 (11)−0.0026 (11)
C220.0132 (14)0.0122 (14)0.0168 (14)−0.0028 (10)−0.0061 (11)−0.0038 (12)
C230.0211 (16)0.0192 (16)0.0171 (15)−0.0079 (12)−0.0042 (13)−0.0024 (13)
C240.0202 (16)0.0174 (16)0.0195 (16)−0.0063 (12)−0.0090 (13)−0.0020 (13)
C250.0188 (16)0.0197 (17)0.0275 (18)−0.0053 (12)−0.0076 (14)−0.0073 (14)
C260.026 (2)0.035 (2)0.034 (2)−0.0072 (15)−0.0130 (17)−0.0120 (18)
C270.0165 (15)0.0186 (16)0.0169 (15)−0.0079 (12)−0.0040 (12)−0.0006 (12)
C280.0233 (17)0.0228 (17)0.0164 (15)−0.0126 (13)−0.0053 (13)0.0007 (13)
C290.0185 (16)0.0252 (18)0.0259 (18)−0.0125 (13)−0.0081 (14)0.0020 (14)
C300.0252 (19)0.029 (2)0.033 (2)−0.0119 (15)−0.0110 (16)−0.0075 (17)

Geometric parameters (Å, °)

Sn1—O92.022 (2)C11—H11C0.9600
Sn1—C82.117 (4)C12—C131.520 (5)
Sn1—C122.125 (3)C12—H12A0.9700
Sn1—O32.200 (2)C12—H12B0.9700
Sn1—O82.243 (2)C13—C141.504 (5)
Sn2—O9i2.044 (2)C13—H13A0.9700
Sn2—C232.121 (3)C13—H13B0.9700
Sn2—C272.133 (3)C14—C151.517 (6)
Sn2—O92.163 (2)C14—H14A0.9700
Sn2—O72.249 (2)C14—H14B0.9700
Sn2—Sn2i3.2982 (4)C15—H15A0.9600
O1—N21.255 (5)C15—H15B0.9600
O2—N21.228 (5)C15—H15C0.9600
O3—C71.301 (4)C16—C171.360 (4)
O4—C71.229 (4)C16—C211.415 (4)
O5—N41.251 (4)C16—H16A0.9300
O6—N41.238 (4)C17—C181.425 (5)
O7—C221.260 (4)C17—H17A0.9300
O8—C22i1.260 (4)C18—C191.415 (5)
O9—Sn2i2.044 (2)C19—C201.409 (4)
N1—C31.357 (5)C20—C211.369 (5)
N1—H1N10.9127C20—H20A0.9300
N1—H2N11.0326C21—C221.499 (4)
N2—C41.439 (5)C22—O8i1.260 (4)
N3—C181.348 (4)C23—C241.527 (5)
N3—H1N30.8828C23—H23A0.9700
N3—H2N30.8795C23—H23B0.9700
N4—C191.439 (4)C24—C251.527 (5)
C1—C21.363 (5)C24—H24A0.9700
C1—C61.404 (5)C24—H24B0.9700
C1—H1A0.9300C25—C261.518 (6)
C2—C31.413 (6)C25—H25A0.9700
C2—H2A0.9300C25—H25B0.9700
C3—C41.408 (5)C26—H26A0.9600
C4—C51.408 (5)C26—H26B0.9600
C5—C61.371 (5)C26—H26C0.9600
C5—H5A0.9300C27—C281.526 (5)
C6—C71.500 (5)C27—H27A0.9700
C8—C91.533 (5)C27—H27B0.9700
C8—H8A0.9700C28—C291.521 (5)
C8—H8B0.9700C28—H28A0.9700
C9—C101.543 (6)C28—H28B0.9700
C9—H9A0.9700C29—C301.517 (5)
C9—H9B0.9700C29—H29A0.9700
C10—C111.528 (7)C29—H29B0.9700
C10—H10A0.9700C30—H30A0.9600
C10—H10B0.9700C30—H30B0.9600
C11—H11A0.9600C30—H30C0.9600
C11—H11B0.9600
O9—Sn1—C8110.89 (12)C13—C12—H12B108.1
O9—Sn1—C12113.25 (12)Sn1—C12—H12B108.1
C8—Sn1—C12135.33 (14)H12A—C12—H12B107.3
O9—Sn1—O378.94 (9)C14—C13—C12114.5 (3)
C8—Sn1—O3100.88 (11)C14—C13—H13A108.6
C12—Sn1—O393.91 (11)C12—C13—H13A108.6
O9—Sn1—O889.41 (9)C14—C13—H13B108.6
C8—Sn1—O884.97 (12)C12—C13—H13B108.6
C12—Sn1—O888.89 (11)H13A—C13—H13B107.6
O3—Sn1—O8168.19 (9)C13—C14—C15112.6 (4)
O9i—Sn2—C23104.84 (12)C13—C14—H14A109.1
O9i—Sn2—C27108.28 (12)C15—C14—H14A109.1
C23—Sn2—C27146.36 (14)C13—C14—H14B109.1
O9i—Sn2—O976.78 (9)C15—C14—H14B109.1
C23—Sn2—O995.98 (11)H14A—C14—H14B107.8
C27—Sn2—O997.07 (11)C14—C15—H15A109.5
O9i—Sn2—O792.75 (9)C14—C15—H15B109.5
C23—Sn2—O787.89 (12)H15A—C15—H15B109.5
C27—Sn2—O784.87 (11)C14—C15—H15C109.5
O9—Sn2—O7169.46 (9)H15A—C15—H15C109.5
O9i—Sn2—Sn2i39.68 (6)H15B—C15—H15C109.5
C23—Sn2—Sn2i103.12 (10)C17—C16—C21121.3 (3)
C27—Sn2—Sn2i105.97 (10)C17—C16—H16A119.4
O9—Sn2—Sn2i37.10 (6)C21—C16—H16A119.4
O7—Sn2—Sn2i132.42 (6)C16—C17—C18121.9 (3)
C7—O3—Sn1116.89 (19)C16—C17—H17A119.1
C22—O7—Sn2133.4 (2)C18—C17—H17A119.1
C22i—O8—Sn1139.1 (2)N3—C18—C19125.8 (3)
Sn1—O9—Sn2i137.06 (11)N3—C18—C17117.9 (3)
Sn1—O9—Sn2119.61 (11)C19—C18—C17116.3 (3)
Sn2i—O9—Sn2103.22 (9)C20—C19—C18120.9 (3)
C3—N1—H1N1121.9C20—C19—N4116.6 (3)
C3—N1—H2N1112.1C18—C19—N4122.5 (3)
H1N1—N1—H2N1125.5C21—C20—C19121.3 (3)
O2—N2—O1121.7 (4)C21—C20—H20A119.4
O2—N2—C4119.9 (3)C19—C20—H20A119.4
O1—N2—C4118.4 (4)C20—C21—C16118.3 (3)
C18—N3—H1N3111.7C20—C21—C22121.0 (3)
C18—N3—H2N3118.7C16—C21—C22120.7 (3)
H1N3—N3—H2N3128.4O7—C22—O8i126.0 (3)
O6—N4—O5121.8 (3)O7—C22—C21117.0 (3)
O6—N4—C19119.5 (3)O8i—C22—C21117.0 (3)
O5—N4—C19118.7 (3)C24—C23—Sn2114.1 (2)
C2—C1—C6122.2 (4)C24—C23—H23A108.7
C2—C1—H1A118.9Sn2—C23—H23A108.7
C6—C1—H1A118.9C24—C23—H23B108.7
C1—C2—C3121.5 (3)Sn2—C23—H23B108.7
C1—C2—H2A119.3H23A—C23—H23B107.6
C3—C2—H2A119.3C25—C24—C23113.0 (3)
N1—C3—C4124.9 (4)C25—C24—H24A109.0
N1—C3—C2118.9 (4)C23—C24—H24A109.0
C4—C3—C2116.2 (3)C25—C24—H24B109.0
C3—C4—C5121.4 (4)C23—C24—H24B109.0
C3—C4—N2122.7 (3)H24A—C24—H24B107.8
C5—C4—N2115.9 (3)C26—C25—C24112.3 (3)
C6—C5—C4121.0 (3)C26—C25—H25A109.1
C6—C5—H5A119.5C24—C25—H25A109.1
C4—C5—H5A119.5C26—C25—H25B109.1
C5—C6—C1117.7 (3)C24—C25—H25B109.1
C5—C6—C7119.6 (3)H25A—C25—H25B107.9
C1—C6—C7122.7 (3)C25—C26—H26A109.5
O4—C7—O3122.2 (3)C25—C26—H26B109.5
O4—C7—C6121.6 (3)H26A—C26—H26B109.5
O3—C7—C6116.2 (3)C25—C26—H26C109.5
C9—C8—Sn1118.1 (2)H26A—C26—H26C109.5
C9—C8—H8A107.8H26B—C26—H26C109.5
Sn1—C8—H8A107.8C28—C27—Sn2115.0 (2)
C9—C8—H8B107.8C28—C27—H27A108.5
Sn1—C8—H8B107.8Sn2—C27—H27A108.5
H8A—C8—H8B107.1C28—C27—H27B108.5
C8—C9—C10112.1 (3)Sn2—C27—H27B108.5
C8—C9—H9A109.2H27A—C27—H27B107.5
C10—C9—H9A109.2C29—C28—C27112.5 (3)
C8—C9—H9B109.2C29—C28—H28A109.1
C10—C9—H9B109.2C27—C28—H28A109.1
H9A—C9—H9B107.9C29—C28—H28B109.1
C11—C10—C9113.5 (4)C27—C28—H28B109.1
C11—C10—H10A108.9H28A—C28—H28B107.8
C9—C10—H10A108.9C30—C29—C28114.2 (3)
C11—C10—H10B108.9C30—C29—H29A108.7
C9—C10—H10B108.9C28—C29—H29A108.7
H10A—C10—H10B107.7C30—C29—H29B108.7
C10—C11—H11A109.5C28—C29—H29B108.7
C10—C11—H11B109.5H29A—C29—H29B107.6
H11A—C11—H11B109.5C29—C30—H30A109.5
C10—C11—H11C109.5C29—C30—H30B109.5
H11A—C11—H11C109.5H30A—C30—H30B109.5
H11B—C11—H11C109.5C29—C30—H30C109.5
C13—C12—Sn1116.8 (2)H30A—C30—H30C109.5
C13—C12—H12A108.1H30B—C30—H30C109.5
Sn1—C12—H12A108.1
O9—Sn1—O3—C7173.3 (3)C5—C6—C7—O3164.7 (3)
C8—Sn1—O3—C7−77.3 (3)C1—C6—C7—O3−15.1 (5)
C12—Sn1—O3—C760.4 (3)O9—Sn1—C8—C983.0 (3)
O8—Sn1—O3—C7163.8 (4)C12—Sn1—C8—C9−106.3 (3)
O9i—Sn2—O7—C22−11.5 (3)O3—Sn1—C8—C90.8 (3)
C23—Sn2—O7—C2293.3 (3)O8—Sn1—C8—C9170.4 (3)
C27—Sn2—O7—C22−119.6 (3)Sn1—C8—C9—C10−166.9 (3)
O9—Sn2—O7—C22−18.5 (7)C8—C9—C10—C1166.1 (5)
Sn2i—Sn2—O7—C22−12.6 (4)O9—Sn1—C12—C13121.2 (3)
O9—Sn1—O8—C22i17.1 (4)C8—Sn1—C12—C13−49.4 (4)
C8—Sn1—O8—C22i−94.0 (4)O3—Sn1—C12—C13−159.2 (3)
C12—Sn1—O8—C22i130.3 (4)O8—Sn1—C12—C1332.3 (3)
O3—Sn1—O8—C22i26.4 (7)Sn1—C12—C13—C14−179.8 (3)
C8—Sn1—O9—Sn2i82.2 (2)C12—C13—C14—C15−179.6 (4)
C12—Sn1—O9—Sn2i−90.8 (2)C21—C16—C17—C18−1.4 (5)
O3—Sn1—O9—Sn2i179.71 (19)C16—C17—C18—N3179.4 (3)
O8—Sn1—O9—Sn2i−2.23 (18)C16—C17—C18—C190.4 (5)
C8—Sn1—O9—Sn2−102.47 (15)N3—C18—C19—C20−178.5 (3)
C12—Sn1—O9—Sn284.59 (15)C17—C18—C19—C200.4 (5)
O3—Sn1—O9—Sn2−4.93 (11)N3—C18—C19—N42.1 (5)
O8—Sn1—O9—Sn2173.13 (13)C17—C18—C19—N4−179.1 (3)
O9i—Sn2—O9—Sn1−176.76 (19)O6—N4—C19—C202.5 (5)
C23—Sn2—O9—Sn179.36 (15)O5—N4—C19—C20−178.9 (3)
C27—Sn2—O9—Sn1−69.56 (15)O6—N4—C19—C18−178.0 (3)
O7—Sn2—O9—Sn1−169.5 (4)O5—N4—C19—C180.6 (5)
Sn2i—Sn2—O9—Sn1−176.76 (19)C18—C19—C20—C21−0.3 (5)
O9i—Sn2—O9—Sn2i0.001 (2)N4—C19—C20—C21179.2 (3)
C23—Sn2—O9—Sn2i−103.88 (13)C19—C20—C21—C16−0.6 (5)
C27—Sn2—O9—Sn2i107.20 (13)C19—C20—C21—C22179.9 (3)
O7—Sn2—O9—Sn2i7.2 (5)C17—C16—C21—C201.4 (5)
C6—C1—C2—C3−0.1 (6)C17—C16—C21—C22−179.0 (3)
C1—C2—C3—N1−179.8 (4)Sn2—O7—C22—O8i3.3 (5)
C1—C2—C3—C41.1 (5)Sn2—O7—C22—C21−178.0 (2)
N1—C3—C4—C5179.8 (4)C20—C21—C22—O7−4.1 (5)
C2—C3—C4—C5−1.3 (5)C16—C21—C22—O7176.3 (3)
N1—C3—C4—N2−1.7 (6)C20—C21—C22—O8i174.7 (3)
C2—C3—C4—N2177.3 (3)C16—C21—C22—O8i−4.9 (5)
O2—N2—C4—C3−175.4 (4)O9i—Sn2—C23—C2427.4 (3)
O1—N2—C4—C33.5 (6)C27—Sn2—C23—C24−142.4 (2)
O2—N2—C4—C53.2 (6)O9—Sn2—C23—C24105.2 (2)
O1—N2—C4—C5−177.9 (4)O7—Sn2—C23—C24−64.9 (3)
C3—C4—C5—C60.4 (5)Sn2i—Sn2—C23—C2468.3 (3)
N2—C4—C5—C6−178.2 (3)Sn2—C23—C24—C25178.1 (2)
C4—C5—C6—C10.7 (5)C23—C24—C25—C26−173.1 (3)
C4—C5—C6—C7−179.1 (3)O9i—Sn2—C27—C28−28.8 (3)
C2—C1—C6—C5−0.8 (5)C23—Sn2—C27—C28140.8 (3)
C2—C1—C6—C7179.0 (3)O9—Sn2—C27—C28−107.1 (2)
Sn1—O3—C7—O412.7 (4)O7—Sn2—C27—C2862.5 (2)
Sn1—O3—C7—C6−164.9 (2)Sn2i—Sn2—C27—C28−70.3 (2)
C5—C6—C7—O4−12.8 (5)Sn2—C27—C28—C29−177.6 (2)
C1—C6—C7—O4167.4 (3)C27—C28—C29—C30−68.9 (4)

Symmetry codes: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 phenyl ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O60.912.593.422 (4)153
N1—H2N1···O11.031.832.644 (5)133
N3—H1N3···O4ii0.882.042.910 (4)167
N3—H2N3···O50.882.062.669 (4)125
C17—H17A···O4ii0.932.513.246 (5)137
C30—H30A···Cg1iii0.962.803.584 (5)139

Symmetry codes: (ii) x+1, y, z−1; (iii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2350).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Khoo, L. E. & Hazell, A. (1999). Acta Cryst. C55, 2070–2073.
  • Li, F.-H., Yin, H.-D., Gao, Z.-J. & Wang, D.-Q. (2006). Acta Cryst. E62, m788–m790.
  • Parvez, M., Sadiq-ur-Rehman,, Shahid, K., Ali, S. & Mazhar, M. (2004). Acta Cryst. E60, m1465–m1467.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Win, Y. F., Teoh, S. G., Ha, S. T., Kia, R. & Fun, H.-K. (2008b). Acta Cryst. E64, m1572–m1573. [PMC free article] [PubMed]
  • Win, Y. F., Teoh, S. G., Lim, E. K., Ng, S. L. & Fun, H. K. (2008a). J. Chem. Crystallogr.38, 345–350.

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