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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1451.
Published online 2009 October 28. doi:  10.1107/S1600536809043554
PMCID: PMC2971378

μ-2-Amino­terephthalato-κ2 O 1:O 4-bis­[triphenyl­tin(IV)]

Abstract

The title compound, [Sn2(C6H5)6(C8H5NO4)], contains two triphenyl­tin groups bridged by a 2-amino­terephthalate ligand. The two SnIV centers have similar distorted tetra­hedral coordination geometries. Each SnIV atom is bonded to three phenyl C atoms and one O atom from a carboxyl­ate group. The other O atom of the carboxyl­ate group has a weak inter­action with the Sn atom. The amino group is disordered over two sites, with site-occupancy factors of 0.779 (11) and 0.221 (11). Intra­molecular N—H(...)O hydrogen bonds are observed.

Related literature

For general background to organotin compounds, see: Hadjikakou & Hadjiliadis (2009 [triangle]). For related structures, see: Chandrasekhar et al. (2003 [triangle]); García-Zarracino & Höpfl (2005 [triangle]); Ma et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1451-scheme1.jpg

Experimental

Crystal data

  • [Sn2(C6H5)6(C8H5NO4)]
  • M r = 879.11
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1451-efi1.jpg
  • a = 16.2933 (14) Å
  • b = 20.6628 (18) Å
  • c = 11.5254 (11) Å
  • β = 93.032 (1)°
  • V = 3874.8 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.33 mm−1
  • T = 298 K
  • 0.23 × 0.12 × 0.10 mm

Data collection

  • Siemens SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.749, T max = 0.878
  • 19986 measured reflections
  • 6817 independent reflections
  • 3977 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.118
  • S = 0.99
  • 6817 reflections
  • 470 parameters
  • H-atom parameters constrained
  • Δρmax = 0.71 e Å−3
  • Δρmin = −0.51 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043554/hy2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043554/hy2231Isup2.hkl

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

Acknowledgments

We acknowledge the Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support. This work was also supported by the Shangdong Tai-Shan Scholar Research Fund.

supplementary crystallographic information

Comment

Tin complexes have attracted much attention for their antitumor properties. Recently, it is noticeable that organotin compounds occupy an important place in cancer chemotherapy (Hadjikakou & Hadjiliadis, 2009). In the last few years, a large number of organotin compounds have been prepared and structurally characterized (Chandrasekhar et al., 2003; García-Zarracino & Höpfl, 2005; Ma et al., 2005). As part of the ongoing study, we report here the synthesis and crystal structure of the title compound.

The title compound possesses a monomeric structure in which two triphenyltin groups are linked together by a 2-aminoterephthalate ligand (Fig. 1). The Sn1—O1 and Sn2—O3 bond distances [2.069 (4) and 2.074 (4) Å] lie in the range of 2.038 (9)–2.115 (6) Å that has been reported as the Sn—O covalent bond length, which proves that the O atoms are coordinated to the Sn atoms by a strong chemical bond. The distances Sn1—O2 [2.810 (5) Å] and Sn2—O4 [2.794 (5) Å] indicate weak interactions between the carbonyl O atoms and the Sn atoms (Table 1). The two Sn centers have similar coordination geometries, each Sn center displaying a tetrahedral coordination environment. The amino group on the benzene-ring is disordered over two positions. Intramolecular hydrogen bonds, N1—H1B···O2 and N1'—H1'2···O4 are observed in the crystal structrue (Table 2).

Experimental

The reaction was carried out under a nitrogen atmosphere. 2-Aminoterephthalic acid (1 mmol) and sodium ethoxide (2.2 mmol) were added to a stirring solution of benzene/methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenyltin chloride (2 mmol) was then added to the reactor and the reaction mixture was stirred for 6 h at 323 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of dichloromethane/methanol (v/v 1:1) to yield yellow blocks of the title compound (yield 85%; m.p. 453 K). Analysis, calculated for C44H35NO4Sn2: C 60.11, H 4.01, N 1.59, O 7.28, Sn 27.00%; found: C 60.09, H 4.00, N 1.60, O 7.30, Sn 27.01%.

Refinement

The atom N1 was found to be disordered over two sites, and the ratio of the occupancy factors was refined to 0.779 (11):0.221 (11) for N1 and N1'. All H atoms were positioned geometrically and refined as riding, with C—H = 0.93, and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C, N).

Figures

Fig. 1.
Molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. The amino group is disordered over two sites, N1 and N1'.

Crystal data

[Sn2(C6H5)6(C8H5NO4)]F(000) = 1752
Mr = 879.11Dx = 1.507 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4322 reflections
a = 16.2933 (14) Åθ = 2.5–25.1°
b = 20.6628 (18) ŵ = 1.33 mm1
c = 11.5254 (11) ÅT = 298 K
β = 93.032 (1)°Needle, yellow
V = 3874.8 (6) Å30.23 × 0.12 × 0.10 mm
Z = 4

Data collection

Siemens SMART 1000 CCD diffractometer6817 independent reflections
Radiation source: fine-focus sealed tube3977 reflections with I > 2σ(I)
graphiteRint = 0.071
[var phi] and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −19→18
Tmin = 0.749, Tmax = 0.878k = −13→24
19986 measured reflectionsl = −13→13

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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3
6817 reflections(Δ/σ)max = 0.001
470 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = −0.51 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Sn10.10099 (2)0.12890 (2)0.47025 (4)0.05219 (15)
Sn20.38411 (2)0.62318 (2)0.50071 (4)0.05156 (15)
N10.2956 (6)0.3125 (4)0.2880 (8)0.114 (4)0.779 (11)
H1A0.32870.33150.24340.137*0.779 (11)
H1B0.28210.27270.27550.137*0.779 (11)
N1'0.1716 (19)0.4464 (14)0.651 (3)0.115 (15)0.221 (11)
H1'10.13910.42640.69570.137*0.221 (11)
H1'20.18400.48630.66490.137*0.221 (11)
O10.1354 (3)0.2228 (2)0.5117 (4)0.0692 (13)
O20.2105 (3)0.2097 (2)0.3578 (4)0.0795 (15)
O30.3397 (3)0.5353 (2)0.4374 (4)0.0675 (13)
O40.2656 (3)0.5431 (2)0.5924 (5)0.0835 (16)
C10.1864 (4)0.2446 (3)0.4355 (7)0.0638 (19)
C20.2869 (4)0.5114 (3)0.5085 (7)0.0607 (18)
C30.2115 (4)0.3142 (3)0.4498 (6)0.0562 (17)
C40.2659 (4)0.3438 (3)0.3745 (6)0.0632 (19)
H40.28660.32090.31310.076*0.221 (11)
C50.2882 (4)0.4090 (3)0.3949 (6)0.0586 (17)
H50.32400.42900.34600.070*
C60.2583 (4)0.4436 (3)0.4849 (6)0.0516 (16)
C70.2036 (4)0.4148 (3)0.5592 (6)0.0596 (18)
H70.18250.43850.61950.072*0.779 (11)
C80.1815 (4)0.3513 (3)0.5423 (6)0.0582 (17)
H80.14590.33210.59260.070*
C90.0258 (4)0.1346 (3)0.3130 (5)0.0515 (16)
C10−0.0170 (5)0.0805 (4)0.2715 (6)0.077 (2)
H10−0.00890.04100.30930.093*
C11−0.0726 (5)0.0839 (5)0.1734 (8)0.104 (3)
H11−0.10120.04730.14720.124*
C12−0.0836 (6)0.1415 (6)0.1178 (7)0.102 (3)
H12−0.12050.14450.05370.122*
C13−0.0408 (6)0.1952 (5)0.1552 (7)0.093 (3)
H13−0.04730.23400.11510.112*
C140.0124 (4)0.1916 (4)0.2533 (6)0.070 (2)
H140.03970.22880.27930.084*
C150.2028 (3)0.0628 (3)0.4790 (6)0.0526 (16)
C160.2554 (4)0.0572 (4)0.3900 (6)0.073 (2)
H160.25160.08630.32830.087*
C170.3143 (5)0.0082 (5)0.3920 (8)0.090 (3)
H170.34910.00390.33110.108*
C180.3205 (5)−0.0344 (4)0.4860 (10)0.094 (3)
H180.3595−0.06730.48800.113*
C190.2698 (5)−0.0278 (4)0.5741 (9)0.095 (3)
H190.2750−0.05610.63670.114*
C200.2104 (4)0.0199 (3)0.5737 (7)0.069 (2)
H200.17590.02360.63520.082*
C210.0269 (4)0.1116 (3)0.6144 (5)0.0509 (15)
C22−0.0530 (4)0.0879 (3)0.6002 (6)0.0553 (16)
H22−0.07500.08000.52550.066*
C23−0.1008 (4)0.0757 (3)0.6940 (6)0.0638 (19)
H23−0.15400.06000.68120.077*
C24−0.0702 (4)0.0868 (4)0.8053 (6)0.072 (2)
H24−0.10190.07860.86840.087*
C250.0088 (5)0.1104 (4)0.8218 (6)0.084 (2)
H250.03010.11820.89700.101*
C260.0568 (4)0.1227 (4)0.7297 (6)0.072 (2)
H260.10980.13860.74370.086*
C270.4553 (3)0.6039 (3)0.6564 (5)0.0492 (15)
C280.4742 (4)0.6534 (4)0.7344 (6)0.0687 (19)
H280.45520.69490.71640.082*
C290.5197 (5)0.6444 (4)0.8370 (7)0.087 (2)
H290.53170.67920.88630.104*
C300.5473 (5)0.5828 (5)0.8659 (7)0.083 (2)
H300.57730.57560.93560.099*
C310.5300 (4)0.5320 (4)0.7901 (7)0.079 (2)
H310.54880.49060.80900.094*
C320.4848 (4)0.5421 (3)0.6863 (6)0.0643 (19)
H320.47410.50750.63600.077*
C330.2954 (4)0.6970 (3)0.5277 (5)0.0516 (16)
C340.2495 (4)0.6946 (3)0.6257 (6)0.0648 (19)
H340.25510.65950.67600.078*
C350.1955 (5)0.7441 (4)0.6493 (7)0.082 (2)
H350.16420.74180.71440.099*
C360.1885 (5)0.7961 (4)0.5766 (9)0.093 (3)
H360.15240.82930.59260.112*
C370.2348 (5)0.8000 (4)0.4785 (8)0.091 (3)
H370.23010.83580.42960.109*
C380.2879 (4)0.7501 (3)0.4550 (6)0.068 (2)
H380.31880.75220.38950.082*
C390.4583 (4)0.6455 (3)0.3583 (5)0.0500 (16)
C400.4259 (4)0.6553 (3)0.2455 (6)0.0621 (18)
H400.36930.65350.23040.075*
C410.4768 (5)0.6679 (4)0.1550 (6)0.075 (2)
H410.45400.67320.07990.090*
C420.5597 (5)0.6725 (4)0.1753 (7)0.083 (2)
H420.59340.68110.11450.100*
C430.5933 (5)0.6645 (4)0.2864 (7)0.085 (2)
H430.64970.66880.30080.102*
C440.5436 (4)0.6500 (4)0.3774 (6)0.068 (2)
H440.56730.64330.45170.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0469 (3)0.0480 (3)0.0620 (3)−0.0044 (2)0.0065 (2)0.0041 (2)
Sn20.0482 (3)0.0452 (3)0.0621 (3)−0.0012 (2)0.0105 (2)0.0023 (2)
N10.135 (8)0.076 (6)0.142 (9)−0.035 (6)0.090 (7)−0.034 (6)
N1'0.13 (3)0.08 (2)0.14 (3)−0.04 (2)0.09 (2)−0.03 (2)
O10.077 (3)0.055 (3)0.077 (3)−0.020 (3)0.015 (3)0.003 (2)
O20.089 (4)0.056 (3)0.096 (4)−0.015 (3)0.028 (3)−0.006 (3)
O30.077 (3)0.052 (3)0.075 (3)−0.023 (3)0.011 (3)−0.005 (2)
O40.089 (4)0.062 (3)0.103 (4)−0.017 (3)0.033 (3)−0.015 (3)
C10.059 (4)0.050 (4)0.083 (5)−0.006 (4)0.007 (4)0.004 (4)
C20.050 (4)0.048 (4)0.084 (5)−0.011 (4)0.005 (4)0.009 (4)
C30.051 (4)0.049 (4)0.069 (5)−0.005 (3)0.000 (3)0.005 (3)
C40.055 (4)0.057 (4)0.080 (5)−0.009 (4)0.019 (4)−0.001 (4)
C50.052 (4)0.057 (4)0.067 (5)−0.015 (4)0.013 (3)0.007 (4)
C60.051 (4)0.041 (4)0.063 (4)−0.004 (3)0.005 (3)0.008 (3)
C70.062 (4)0.054 (4)0.063 (4)−0.018 (4)0.013 (3)0.004 (4)
C80.052 (4)0.060 (4)0.064 (4)−0.011 (4)0.013 (3)0.018 (4)
C90.051 (4)0.054 (4)0.050 (4)0.009 (3)0.008 (3)0.006 (3)
C100.091 (5)0.065 (5)0.073 (5)0.020 (5)−0.013 (4)−0.009 (4)
C110.104 (7)0.108 (8)0.095 (7)0.012 (6)−0.026 (6)−0.026 (6)
C120.103 (7)0.141 (9)0.060 (5)0.042 (7)−0.009 (5)0.001 (6)
C130.095 (7)0.121 (8)0.065 (6)0.041 (6)0.016 (5)0.038 (5)
C140.064 (4)0.071 (5)0.077 (5)0.011 (4)0.013 (4)0.016 (4)
C150.034 (3)0.059 (4)0.065 (4)−0.007 (3)0.001 (3)−0.007 (4)
C160.056 (4)0.078 (5)0.083 (5)−0.001 (4)0.003 (4)−0.017 (4)
C170.058 (5)0.094 (7)0.119 (8)0.000 (5)0.017 (5)−0.031 (6)
C180.060 (5)0.071 (6)0.149 (9)0.016 (5)−0.012 (6)−0.025 (6)
C190.070 (5)0.067 (6)0.144 (9)0.004 (5)−0.018 (6)0.012 (6)
C200.056 (4)0.065 (5)0.085 (5)−0.004 (4)−0.001 (4)0.003 (4)
C210.050 (3)0.040 (4)0.063 (4)−0.010 (3)−0.001 (3)0.010 (3)
C220.053 (4)0.057 (4)0.054 (4)−0.009 (4)−0.004 (3)0.003 (3)
C230.044 (4)0.064 (5)0.084 (5)−0.006 (4)0.007 (4)−0.002 (4)
C240.069 (5)0.083 (5)0.066 (5)−0.008 (5)0.020 (4)−0.013 (4)
C250.081 (5)0.110 (7)0.062 (5)−0.021 (5)0.010 (4)−0.027 (5)
C260.055 (4)0.094 (6)0.066 (4)−0.021 (4)0.005 (3)−0.025 (5)
C270.041 (3)0.053 (4)0.055 (4)−0.001 (3)0.015 (3)0.002 (3)
C280.085 (5)0.057 (4)0.065 (5)0.005 (4)0.008 (4)0.001 (4)
C290.100 (6)0.090 (6)0.069 (5)−0.003 (5)0.000 (5)−0.005 (5)
C300.079 (5)0.103 (7)0.066 (5)0.004 (6)−0.002 (4)0.016 (5)
C310.073 (5)0.067 (5)0.095 (6)0.015 (5)0.003 (5)0.025 (5)
C320.064 (4)0.051 (4)0.078 (5)0.010 (4)0.003 (4)0.003 (4)
C330.044 (3)0.051 (4)0.060 (4)0.003 (3)−0.002 (3)−0.001 (3)
C340.066 (4)0.068 (5)0.061 (4)0.010 (4)0.009 (4)−0.003 (4)
C350.076 (5)0.085 (6)0.086 (6)0.021 (5)0.015 (4)−0.006 (5)
C360.078 (6)0.075 (6)0.125 (8)0.033 (5)−0.002 (6)−0.030 (6)
C370.108 (7)0.061 (5)0.102 (7)0.019 (5)−0.002 (6)0.011 (5)
C380.070 (5)0.058 (4)0.076 (5)0.009 (4)0.004 (4)−0.004 (4)
C390.050 (4)0.038 (3)0.064 (4)0.001 (3)0.018 (3)0.005 (3)
C400.059 (4)0.064 (4)0.064 (5)0.001 (4)0.004 (4)−0.004 (4)
C410.086 (6)0.085 (6)0.055 (5)−0.013 (5)0.005 (4)0.004 (4)
C420.090 (6)0.079 (6)0.083 (6)−0.008 (5)0.034 (5)0.005 (5)
C430.059 (5)0.099 (7)0.099 (7)−0.007 (5)0.016 (4)0.017 (5)
C440.057 (4)0.079 (5)0.070 (5)−0.009 (4)0.009 (4)0.012 (4)

Geometric parameters (Å, °)

Sn1—O12.069 (4)C18—C191.349 (11)
Sn1—O22.810 (5)C18—H180.9300
Sn1—C92.137 (6)C19—C201.381 (10)
Sn1—C152.147 (6)C19—H190.9300
Sn1—C212.134 (6)C20—H200.9300
Sn2—O32.074 (4)C21—C221.392 (8)
Sn2—O42.794 (5)C21—C261.410 (8)
Sn2—C272.122 (6)C22—C231.389 (8)
Sn2—C332.135 (6)C22—H220.9300
Sn2—C392.140 (6)C23—C241.371 (9)
N1—C41.303 (9)C23—H230.9300
N1—H1A0.8600C24—C251.380 (9)
N1—H1B0.8600C24—H240.9300
N1'—C71.37 (3)C25—C261.375 (9)
N1'—H1'10.8600C25—H250.9300
N1'—H1'20.8600C26—H260.9300
O1—C11.320 (8)C27—C281.387 (9)
O2—C11.230 (8)C27—C321.401 (8)
O3—C21.315 (8)C28—C291.374 (10)
O4—C21.234 (8)C28—H280.9300
C1—C31.502 (9)C29—C301.385 (11)
C2—C61.495 (9)C29—H290.9300
C3—C41.412 (8)C30—C311.386 (10)
C3—C81.420 (9)C30—H300.9300
C4—C51.412 (9)C31—C321.387 (9)
C4—H40.9300C31—H310.9300
C5—C61.371 (8)C32—H320.9300
C5—H50.9300C33—C381.382 (9)
C6—C71.401 (8)C33—C341.388 (8)
C7—C81.372 (9)C34—C351.385 (9)
C7—H70.9300C34—H340.9300
C8—H80.9300C35—C361.364 (11)
C9—C141.375 (9)C35—H350.9300
C9—C101.390 (9)C36—C371.394 (11)
C10—C111.413 (10)C36—H360.9300
C10—H100.9300C37—C381.382 (10)
C11—C121.360 (12)C37—H370.9300
C11—H110.9300C38—H380.9300
C12—C131.367 (12)C39—C401.392 (8)
C12—H120.9300C39—C441.398 (8)
C13—C141.389 (10)C40—C411.390 (9)
C13—H130.9300C40—H400.9300
C14—H140.9300C41—C421.363 (10)
C15—C161.376 (9)C41—H410.9300
C15—C201.406 (9)C42—C431.375 (10)
C16—C171.395 (10)C42—H420.9300
C16—H160.9300C43—C441.391 (9)
C17—C181.396 (12)C43—H430.9300
C17—H170.9300C44—H440.9300
O1—Sn1—C2197.7 (2)C16—C17—C18119.5 (8)
O1—Sn1—C9106.3 (2)C16—C17—H17120.3
C21—Sn1—C9110.3 (2)C18—C17—H17120.3
O1—Sn1—C15112.7 (2)C19—C18—C17119.8 (9)
C21—Sn1—C15108.9 (2)C19—C18—H18120.1
C9—Sn1—C15118.8 (2)C17—C18—H18120.1
O1—Sn1—O251.56 (16)C18—C19—C20121.8 (9)
C21—Sn1—O2149.03 (19)C18—C19—H19119.1
C9—Sn1—O285.7 (2)C20—C19—H19119.1
C15—Sn1—O283.8 (2)C19—C20—C15119.0 (8)
O3—Sn2—C27107.3 (2)C19—C20—H20120.5
O3—Sn2—C33116.7 (2)C15—C20—H20120.5
C27—Sn2—C33110.8 (2)C22—C21—C26116.2 (6)
O3—Sn2—C3996.9 (2)C22—C21—Sn1122.1 (5)
C27—Sn2—C39112.5 (2)C26—C21—Sn1121.7 (4)
C33—Sn2—C39111.9 (2)C23—C22—C21122.2 (6)
O3—Sn2—O451.58 (16)C23—C22—H22118.9
C27—Sn2—O485.79 (19)C21—C22—H22118.9
C33—Sn2—O483.2 (2)C24—C23—C22120.4 (6)
C39—Sn2—O4148.0 (2)C24—C23—H23119.8
C4—N1—H1A120.0C22—C23—H23119.8
C4—N1—H1B120.0C23—C24—C25118.6 (7)
H1A—N1—H1B120.0C23—C24—H24120.7
C7—N1'—H1'1120.0C25—C24—H24120.7
C7—N1'—H1'2120.0C26—C25—C24121.5 (7)
H1'1—N1'—H1'2120.0C26—C25—H25119.2
C1—O1—Sn1109.8 (4)C24—C25—H25119.2
C1—O2—Sn177.2 (4)C25—C26—C21121.1 (6)
C2—O3—Sn2109.7 (4)C25—C26—H26119.5
C2—O4—Sn277.8 (4)C21—C26—H26119.5
O2—C1—O1121.4 (6)C28—C27—C32116.9 (6)
O2—C1—C3123.1 (6)C28—C27—Sn2120.1 (5)
O1—C1—C3115.5 (7)C32—C27—Sn2123.0 (5)
O4—C2—O3120.6 (6)C29—C28—C27123.3 (7)
O4—C2—C6122.8 (6)C29—C28—H28118.4
O3—C2—C6116.5 (7)C27—C28—H28118.4
C4—C3—C8118.7 (6)C28—C29—C30119.0 (8)
C4—C3—C1121.5 (6)C28—C29—H29120.5
C8—C3—C1119.8 (6)C30—C29—H29120.5
N1—C4—C5119.9 (7)C29—C30—C31119.5 (7)
N1—C4—C3121.7 (7)C29—C30—H30120.3
C5—C4—C3118.4 (7)C31—C30—H30120.3
N1—C4—H40.9C30—C31—C32120.7 (7)
C5—C4—H4120.8C30—C31—H31119.6
C3—C4—H4120.8C32—C31—H31119.6
C6—C5—C4121.7 (6)C31—C32—C27120.6 (7)
C6—C5—H5119.2C31—C32—H32119.7
C4—C5—H5119.2C27—C32—H32119.7
C5—C6—C7120.3 (6)C38—C33—C34119.1 (6)
C5—C6—C2120.4 (6)C38—C33—Sn2121.2 (5)
C7—C6—C2119.3 (6)C34—C33—Sn2119.4 (5)
C8—C7—N1'117.2 (13)C35—C34—C33120.6 (7)
C8—C7—C6119.4 (7)C35—C34—H34119.7
N1'—C7—C6123.4 (13)C33—C34—H34119.7
C8—C7—H7120.3C36—C35—C34119.6 (8)
N1'—C7—H73.3C36—C35—H35120.2
C6—C7—H7120.3C34—C35—H35120.2
C7—C8—C3121.6 (6)C35—C36—C37120.9 (8)
C7—C8—H8119.2C35—C36—H36119.6
C3—C8—H8119.2C37—C36—H36119.6
C14—C9—C10116.9 (6)C38—C37—C36119.2 (8)
C14—C9—Sn1122.7 (5)C38—C37—H37120.4
C10—C9—Sn1120.1 (5)C36—C37—H37120.4
C9—C10—C11121.6 (7)C37—C38—C33120.6 (7)
C9—C10—H10119.2C37—C38—H38119.7
C11—C10—H10119.2C33—C38—H38119.7
C12—C11—C10118.9 (9)C40—C39—C44117.5 (6)
C12—C11—H11120.6C40—C39—Sn2123.1 (5)
C10—C11—H11120.6C44—C39—Sn2119.4 (5)
C11—C12—C13120.7 (8)C41—C40—C39121.1 (6)
C11—C12—H12119.7C41—C40—H40119.5
C13—C12—H12119.7C39—C40—H40119.5
C12—C13—C14119.9 (8)C42—C41—C40120.6 (7)
C12—C13—H13120.0C42—C41—H41119.7
C14—C13—H13120.0C40—C41—H41119.7
C9—C14—C13121.9 (8)C41—C42—C43119.6 (7)
C9—C14—H14119.0C41—C42—H42120.2
C13—C14—H14119.0C43—C42—H42120.2
C16—C15—C20119.6 (7)C42—C43—C44120.6 (7)
C16—C15—Sn1121.9 (5)C42—C43—H43119.7
C20—C15—Sn1118.3 (5)C44—C43—H43119.7
C15—C16—C17120.2 (8)C43—C44—C39120.6 (7)
C15—C16—H16119.9C43—C44—H44119.7
C17—C16—H16119.9C39—C44—H44119.7

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O20.862.022.683 (9)133
N1'—H1'2···O40.861.992.63 (3)130

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2231).

References

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  • Hadjikakou, S. K. & Hadjiliadis, N. (2009). Coord. Chem. Rev.253, 235–249.
  • Ma, C., Han, Y., Zhang, R. & Wang, D. (2005). Eur. J. Inorg. Chem. pp. 3024–3033.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
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