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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1222.
Published online 2010 September 8. doi:  10.1107/S1600536810035221
PMCID: PMC2983362

catena-Poly[[tribenzyl­tin(IV)]-μ-2-(piperidin-1-ylcarbothio­ylsulfan­yl)acetato-κ2 O:O′]

Abstract

The Sn atom in the title polymeric compound, [Sn(C7H7)3(C8H12NO2S2)]n, exists in a trans-C3O2 trigonal-bipyramidal coordination environment in the two independent formula units. The carboxyl­ate moiety functions in a bridging mode, linking adjacent triorganotin cations into a linear chain running along the shortest axis of the triclinic unit cell; the repeat distance of the polymer is half the a-axial length. In one formula unit, the Sn atom is displaced out of the equatorial plane in the direction of the Sn—Ocovalent bond by 0.093 (4) Å and in the second mol­ecule, the Sn atom is displaced by 0.105 (4) Å in the same direction.

Related literature

Trialkyl­tin carboxyl­ates are generally carboxyl­ate-bridged polymers, see: Ng et al. (1988 [triangle]). For the direct synthesis of substituted tribenzyl­tin chlorides, see: Sisido et al. (1961 [triangle]). For the synthesis of dithio­carbamoyl­acetic acids, see: Nachmias (1952 [triangle]). For background to the triorganotin derivatives of dithio­carbamyl­acetic acids, see: Ng & Kumar Das (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1222-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H7)3(C8H12NO2S2)]
  • M r = 610.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1222-efi1.jpg
  • a = 10.7500 (7) Å
  • b = 11.3594 (7) Å
  • c = 12.5494 (8) Å
  • α = 79.494 (1)°
  • β = 81.890 (1)°
  • γ = 75.294 (1)°
  • V = 1450.15 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.05 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.744, T max = 0.902
  • 13931 measured reflections
  • 11121 independent reflections
  • 9448 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.095
  • S = 1.03
  • 11121 reflections
  • 559 parameters
  • 89 restraints
  • H-atom parameters constrained
  • Δρmax = 0.75 e Å−3
  • Δρmin = −0.41 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4513 Friedel pairs
  • Flack parameter: −0.01 (2)

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035221/bt5336sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035221/bt5336Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

Trialkyltin carboxylates are generally exists as carboxylate-bridged polymers (Ng et al., 1988). We have reported the triorganotin derivatives of dithiocarbamylacetic acids, a class plant growth hormones (Ng & Kumar Das, 1991). The title tribenzyltin derivative crystallizes as two independent formula units; both have their tin atoms in a trans-C3SnO2 trigonal bipyramidal coordination environment (Figs. 1 and 2.) The carboxylate portion functions in a bridging mode to link adjacent triorganotin cations into a linear chain running along the shortest axis of the triclinic unit cell (Fig. 3).

Experimental

Pentamethylenedithiocarbomylacetic acid was synthesized from piperidine, carbon disulfide and chloroacetic acid (Nachmias, 1952). Tribenzyltin chloride was prepared by direct synthesis from benzyl chloride and tin powder in a mixture of toluene and water (Sisido et al., 1961). The triorganotin chloride was hydrolyzed with dilute sodium hydroxide solution to give tribenzyltin hydroxide. The carboxylic acid (0.14 g, 0.73 mmol) and the organotin hydroxide (0.30 g, 0.73 mmol) were heated in ethanol (100 ml) for 2 hours. After filtering the mixture, colorless crystals were obtained upon slow evaporation of the filtrate.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.93–0.97 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2 times Ueq(C).

The aromatic rings of the benzyl chains were refined as rigid hexagons of 1.39 Å sides. The carbon–carbon bond distances in the piperidinyl rings were tightly restrained to 1.500+0.005 Å and the 1,3-related carbon–carbon distances to 2.350+0.005 Å. The anisotropic displacement parameters of the carbon atoms of the piperidinyl rings were restrained to be nearly isotropic.

In the dithiocarbamato C2N–C fragment, the nitrogen–carbonsulfur distances were restrained to 1.35±0.01 Å and the nitrogen–carbonmethylene distances to 1.45±0.01 Å.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of one of the two independent formula of Sn(C7H7)3(C8H12NO2S2) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the second formula unit of Sn(C7H7)3(C8H12NO2S2) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The symmetry code is given in Table 1.
Fig. 3.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the chain structure of polymeric Sn(C7H7)3(C8H12NO2S2) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn(C7H7)3(C8H12NO2S2)]Z = 2
Mr = 610.37F(000) = 624
Triclinic, P1Dx = 1.398 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7500 (7) ÅCell parameters from 6011 reflections
b = 11.3594 (7) Åθ = 2.3–24.8°
c = 12.5494 (8) ŵ = 1.05 mm1
α = 79.494 (1)°T = 293 K
β = 81.890 (1)°Wedge, yellow
γ = 75.294 (1)°0.30 × 0.20 × 0.10 mm
V = 1450.15 (16) Å3

Data collection

Bruker SMART APEX diffractometer11121 independent reflections
Radiation source: fine-focus sealed tube9448 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.744, Tmax = 0.902k = −14→13
13931 measured reflectionsl = −16→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.095w = 1/[σ2(Fo2) + (0.0488P)2 + ] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
11121 reflectionsΔρmax = 0.75 e Å3
559 parametersΔρmin = −0.41 e Å3
89 restraintsAbsolute structure: Flack (1983), 4513 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (2)

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

xyzUiso*/Ueq
Sn10.49998 (2)0.49997 (2)1.00002 (2)0.04882 (10)
Sn2−0.01462 (2)0.60583 (2)0.92111 (2)0.04867 (10)
S10.21418 (18)0.20712 (15)1.19010 (12)0.0717 (4)
S20.1212 (3)0.4148 (2)1.31804 (19)0.1085 (7)
S3−0.39487 (16)0.89805 (15)0.73173 (13)0.0716 (4)
S4−0.3672 (4)0.7164 (3)0.5797 (3)0.1691 (17)
O10.3468 (3)0.3924 (4)1.0643 (3)0.0622 (9)
O20.1838 (3)0.5164 (4)0.9783 (3)0.0584 (9)
O3−0.2056 (3)0.7115 (3)0.8561 (3)0.0627 (9)
O4−0.3317 (3)0.5915 (4)0.9437 (3)0.0560 (9)
N10.2493 (5)0.1888 (5)1.3937 (4)0.0744 (13)
N2−0.3464 (10)0.9487 (7)0.5250 (5)0.134 (4)
C10.6270 (5)0.3575 (5)1.0974 (5)0.0630 (14)
H1A0.60220.28031.10120.076*
H1B0.71440.34801.06190.076*
C20.6259 (4)0.3822 (4)1.2114 (3)0.0600 (13)
C30.7312 (4)0.4127 (5)1.2428 (4)0.089 (2)
H30.80390.41661.19360.106*
C40.7280 (6)0.4374 (5)1.3478 (5)0.136 (4)
H40.79840.45781.36880.163*
C50.6194 (7)0.4316 (5)1.4213 (3)0.123 (3)
H50.61720.44811.49160.147*
C60.5141 (5)0.4011 (5)1.3899 (3)0.109 (3)
H60.44140.39721.43910.131*
C70.5173 (3)0.3764 (5)1.2850 (4)0.0745 (17)
H70.44690.35601.26390.089*
C80.3774 (5)0.6484 (5)1.0777 (5)0.0651 (14)
H8A0.30610.68591.03380.078*
H8B0.34110.61231.14740.078*
C90.4324 (4)0.7496 (3)1.0979 (4)0.0598 (17)
C100.5249 (4)0.7246 (3)1.1711 (4)0.0809 (18)
H100.55230.64501.20750.097*
C110.5763 (4)0.8186 (5)1.1901 (4)0.107 (3)
H110.63810.80191.23910.129*
C120.5353 (5)0.9376 (4)1.1359 (5)0.106 (3)
H120.56981.00051.14860.128*
C130.4429 (5)0.9626 (3)1.0626 (4)0.093 (2)
H130.41551.04231.02630.112*
C140.3915 (4)0.8687 (4)1.0436 (3)0.0708 (18)
H140.32960.88540.99460.085*
C150.4934 (5)0.4621 (5)0.8392 (5)0.0613 (13)
H15A0.41040.44560.83420.074*
H15B0.50300.53350.78590.074*
C160.5989 (3)0.3537 (4)0.8154 (3)0.0635 (15)
C170.5921 (5)0.2361 (4)0.8673 (4)0.078 (2)
H170.52080.22480.91600.093*
C180.6917 (7)0.1354 (3)0.8465 (5)0.118 (3)
H180.68720.05680.88130.142*
C190.7982 (5)0.1523 (5)0.7738 (5)0.129 (4)
H190.86490.08490.75990.155*
C200.8050 (4)0.2698 (7)0.7219 (4)0.128 (4)
H200.87620.28110.67320.153*
C210.7053 (4)0.3705 (5)0.7427 (3)0.0796 (18)
H210.70990.44920.70790.096*
C220.0666 (6)0.7431 (5)0.8139 (5)0.0632 (14)
H22A0.00150.82010.80730.076*
H22B0.13780.75590.84650.076*
C230.1147 (3)0.7116 (4)0.7022 (3)0.0615 (13)
C240.2466 (3)0.6838 (4)0.6700 (4)0.0773 (17)
H240.30470.68980.71600.093*
C250.2918 (4)0.6470 (5)0.5690 (4)0.108 (3)
H250.38010.62840.54750.129*
C260.2050 (6)0.6381 (5)0.5003 (3)0.120 (3)
H260.23530.61350.43270.144*
C270.0731 (6)0.6659 (6)0.5325 (4)0.110 (3)
H270.01510.65990.48650.132*
C280.0279 (3)0.7027 (5)0.6335 (4)0.087 (2)
H28−0.06030.72130.65500.104*
C29−0.0347 (5)0.4565 (5)0.8470 (5)0.0593 (13)
H29A−0.10400.42370.89010.071*
H29B−0.06430.49190.77600.071*
C300.0768 (3)0.3491 (3)0.8305 (3)0.0507 (14)
C310.0646 (4)0.2318 (4)0.8786 (3)0.0695 (18)
H31−0.01260.22070.91820.083*
C320.1677 (5)0.1309 (3)0.8674 (4)0.089 (2)
H320.15960.05230.89960.107*
C330.2831 (4)0.1474 (4)0.8082 (4)0.095 (2)
H330.35210.07990.80070.114*
C340.2952 (3)0.2648 (4)0.7601 (3)0.0807 (19)
H340.37240.27580.72050.097*
C350.1921 (4)0.3656 (3)0.7713 (3)0.0643 (14)
H350.20020.44420.73920.077*
C36−0.0906 (6)0.6499 (5)1.0801 (5)0.0614 (13)
H36A−0.18390.66301.08750.074*
H36B−0.05680.58121.13470.074*
C37−0.0549 (4)0.7638 (3)1.0994 (3)0.0590 (14)
C38−0.1172 (4)0.8787 (4)1.0485 (3)0.079 (2)
H38−0.18270.88531.00520.095*
C39−0.0815 (5)0.9838 (3)1.0626 (4)0.092 (2)
H39−0.12321.06071.02860.110*
C400.0164 (5)0.9740 (4)1.1274 (4)0.100 (3)
H400.04031.04431.13680.120*
C410.0787 (4)0.8591 (5)1.1783 (4)0.097 (3)
H410.14420.85251.22170.116*
C420.0430 (3)0.7540 (4)1.1642 (3)0.0714 (16)
H420.08460.67711.19820.086*
C430.2326 (5)0.4219 (5)1.0437 (4)0.0537 (12)
C440.1470 (6)0.3360 (7)1.0941 (5)0.0790 (19)
H44A0.12040.30531.03590.095*
H44B0.06970.38361.13010.095*
C450.1957 (6)0.2699 (5)1.3110 (4)0.0643 (14)
C460.3030 (8)0.0580 (7)1.3936 (6)0.114 (3)
H46A0.38220.03141.42910.136*
H46B0.32220.04011.31960.136*
C470.2029 (11)−0.0070 (9)1.4547 (8)0.159 (4)
H47A0.12100.02501.42360.190*
H47B0.2302−0.09471.45220.190*
C480.1908 (11)0.0177 (7)1.5682 (6)0.157 (5)
H48A0.1386−0.03261.61580.188*
H48B0.2753−0.00101.59450.188*
C490.1281 (6)0.1499 (7)1.5662 (6)0.106 (3)
H49A0.10600.16931.63970.128*
H49B0.04990.17151.52960.128*
C500.2245 (7)0.2179 (7)1.5054 (5)0.094 (2)
H50A0.19110.30581.50430.113*
H50B0.30400.19291.54040.113*
C51−0.3112 (4)0.6835 (5)0.8757 (4)0.0492 (11)
C52−0.4235 (5)0.7622 (6)0.8183 (5)0.0753 (17)
H52A−0.49470.78640.87260.090*
H52B−0.45060.71260.77470.090*
C53−0.3661 (9)0.8566 (8)0.6014 (5)0.104 (3)
C54−0.3379 (7)1.0693 (8)0.5407 (7)0.099 (3)
H54A−0.35531.07790.61720.119*
H54B−0.39951.13320.50020.119*
C55−0.2030 (8)1.0779 (11)0.4995 (7)0.138 (4)
H55A−0.14121.00800.53320.166*
H55B−0.18641.15300.51470.166*
C56−0.1936 (11)1.0785 (10)0.3797 (7)0.165 (5)
H56A−0.11361.09830.34440.198*
H56B−0.26561.13840.34800.198*
C57−0.1970 (9)0.9511 (10)0.3672 (8)0.154 (4)
H57A−0.17840.93960.29130.185*
H57B−0.13440.89030.40930.185*
C58−0.3305 (10)0.9407 (11)0.4087 (7)0.154 (4)
H58A−0.39281.00680.37090.184*
H58B−0.34380.86270.39750.184*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.04022 (18)0.0499 (2)0.0563 (2)−0.01081 (16)−0.00841 (15)−0.00493 (17)
Sn20.0437 (2)0.0493 (2)0.0570 (2)−0.01849 (17)−0.00312 (16)−0.00898 (17)
S10.1022 (11)0.0663 (9)0.0563 (8)−0.0390 (8)−0.0048 (7)−0.0097 (7)
S20.150 (2)0.0718 (12)0.1005 (15)−0.0089 (12)−0.0197 (13)−0.0243 (10)
S30.0854 (10)0.0612 (9)0.0606 (9)−0.0079 (7)−0.0045 (7)−0.0051 (7)
S40.245 (4)0.163 (3)0.154 (3)−0.148 (3)0.064 (3)−0.089 (2)
O10.0495 (19)0.067 (2)0.071 (2)−0.0237 (17)−0.0126 (17)0.0073 (18)
O20.0448 (17)0.068 (2)0.065 (2)−0.0227 (16)−0.0094 (15)−0.0014 (19)
O30.0461 (19)0.060 (2)0.082 (3)−0.0172 (17)−0.0094 (17)−0.0016 (18)
O40.0423 (17)0.066 (2)0.062 (2)−0.0166 (15)−0.0087 (15)−0.0063 (18)
N10.080 (3)0.083 (4)0.057 (3)−0.020 (3)−0.007 (2)−0.003 (3)
N20.227 (10)0.157 (8)0.060 (4)−0.126 (8)0.020 (5)−0.032 (4)
C10.048 (3)0.061 (3)0.073 (4)−0.006 (2)−0.012 (2)0.001 (3)
C20.054 (3)0.053 (3)0.073 (4)−0.012 (2)−0.017 (2)−0.001 (2)
C30.088 (4)0.080 (4)0.107 (5)−0.031 (4)−0.047 (4)0.009 (4)
C40.163 (10)0.119 (8)0.157 (10)−0.075 (7)−0.099 (8)0.026 (7)
C50.183 (10)0.089 (6)0.105 (7)−0.018 (6)−0.073 (7)−0.010 (5)
C60.113 (6)0.115 (7)0.080 (5)−0.002 (5)−0.009 (5)0.001 (5)
C70.076 (4)0.071 (4)0.075 (4)−0.018 (3)−0.019 (3)0.005 (3)
C80.043 (2)0.067 (4)0.083 (4)−0.007 (2)0.000 (2)−0.019 (3)
C90.045 (3)0.069 (4)0.063 (4)−0.007 (3)0.005 (2)−0.020 (3)
C100.090 (4)0.065 (4)0.086 (4)0.002 (3)−0.030 (4)−0.021 (3)
C110.094 (5)0.114 (6)0.125 (7)0.006 (5)−0.039 (5)−0.071 (6)
C120.107 (6)0.082 (5)0.145 (8)−0.032 (5)0.010 (5)−0.060 (5)
C130.100 (5)0.063 (4)0.115 (6)−0.015 (4)−0.009 (4)−0.017 (4)
C140.074 (4)0.056 (4)0.080 (5)−0.003 (3)−0.013 (3)−0.019 (4)
C150.059 (3)0.063 (3)0.067 (3)−0.019 (3)−0.019 (3)−0.008 (3)
C160.065 (3)0.069 (4)0.068 (4)−0.019 (3)−0.024 (3)−0.020 (3)
C170.087 (5)0.065 (5)0.092 (6)−0.028 (4)−0.030 (4)−0.010 (4)
C180.148 (8)0.075 (5)0.138 (8)0.014 (5)−0.072 (7)−0.047 (5)
C190.129 (8)0.115 (7)0.149 (9)0.037 (6)−0.070 (7)−0.084 (7)
C200.069 (4)0.201 (12)0.130 (7)−0.010 (6)−0.003 (4)−0.105 (8)
C210.073 (4)0.101 (5)0.078 (4)−0.025 (4)−0.007 (3)−0.040 (4)
C220.057 (3)0.061 (3)0.074 (4)−0.023 (3)−0.003 (3)−0.005 (3)
C230.053 (3)0.058 (3)0.071 (4)−0.018 (2)−0.004 (2)0.001 (3)
C240.058 (3)0.073 (4)0.092 (5)−0.021 (3)0.007 (3)0.005 (3)
C250.089 (5)0.095 (6)0.117 (7)−0.012 (4)0.036 (5)−0.009 (5)
C260.138 (8)0.127 (7)0.081 (6)−0.025 (6)0.028 (5)−0.014 (5)
C270.143 (8)0.133 (8)0.062 (5)−0.048 (6)−0.016 (5)−0.009 (5)
C280.071 (4)0.103 (6)0.080 (5)−0.019 (4)−0.013 (3)0.006 (4)
C290.054 (3)0.056 (3)0.077 (4)−0.018 (2)−0.015 (2)−0.019 (3)
C300.054 (3)0.049 (3)0.055 (3)−0.014 (2)−0.016 (2)−0.012 (3)
C310.080 (4)0.064 (5)0.064 (4)−0.017 (3)−0.014 (3)0.000 (3)
C320.114 (6)0.068 (4)0.081 (5)−0.003 (4)−0.030 (4)−0.011 (3)
C330.091 (5)0.087 (5)0.095 (5)0.028 (4)−0.037 (4)−0.033 (4)
C340.063 (4)0.108 (6)0.082 (4)−0.021 (3)−0.011 (3)−0.042 (4)
C350.055 (3)0.075 (4)0.071 (4)−0.021 (3)−0.005 (2)−0.027 (3)
C360.058 (3)0.068 (4)0.064 (3)−0.026 (3)0.001 (2)−0.015 (3)
C370.061 (3)0.066 (4)0.055 (3)−0.027 (3)0.011 (3)−0.018 (3)
C380.099 (6)0.070 (5)0.072 (5)−0.023 (5)−0.011 (4)−0.015 (4)
C390.128 (6)0.077 (5)0.083 (5)−0.053 (4)−0.001 (4)−0.012 (4)
C400.116 (6)0.096 (6)0.110 (6)−0.066 (5)0.030 (5)−0.048 (5)
C410.065 (4)0.143 (8)0.106 (6)−0.042 (4)0.005 (4)−0.066 (6)
C420.054 (3)0.088 (4)0.078 (4)−0.015 (3)−0.004 (3)−0.031 (3)
C430.051 (2)0.071 (3)0.049 (3)−0.029 (2)−0.006 (2)−0.012 (2)
C440.080 (4)0.112 (5)0.063 (4)−0.060 (4)−0.024 (3)0.004 (3)
C450.077 (3)0.069 (3)0.054 (3)−0.032 (3)−0.006 (2)−0.006 (3)
C460.111 (5)0.111 (6)0.102 (6)0.011 (5)−0.027 (4)−0.012 (5)
C470.197 (9)0.123 (7)0.159 (8)−0.056 (7)−0.004 (7)−0.014 (6)
C480.176 (8)0.167 (9)0.119 (7)−0.054 (7)−0.005 (6)0.012 (6)
C490.085 (4)0.153 (7)0.079 (4)−0.032 (5)0.004 (4)−0.016 (5)
C500.102 (5)0.117 (5)0.066 (4)−0.031 (4)−0.019 (3)−0.009 (4)
C510.042 (2)0.052 (3)0.054 (3)−0.007 (2)−0.0028 (19)−0.014 (2)
C520.052 (3)0.087 (4)0.075 (4)−0.013 (3)−0.005 (3)0.014 (3)
C530.134 (6)0.140 (7)0.069 (4)−0.093 (6)0.023 (4)−0.036 (5)
C540.102 (5)0.098 (5)0.083 (5)−0.001 (4)0.001 (4)−0.013 (4)
C550.150 (7)0.147 (7)0.138 (7)−0.061 (6)0.006 (6)−0.054 (6)
C560.180 (9)0.156 (9)0.144 (8)−0.046 (7)0.030 (7)−0.009 (7)
C570.163 (8)0.177 (8)0.113 (6)−0.029 (7)0.034 (6)−0.051 (6)
C580.169 (8)0.196 (9)0.121 (7)−0.075 (7)−0.009 (6)−0.048 (6)

Geometric parameters (Å, °)

Sn1—C12.146 (5)C23—C281.3900
Sn1—C82.153 (5)C24—C251.3900
Sn1—C152.152 (5)C24—H240.9300
Sn1—O12.268 (3)C25—C261.3900
Sn1—O4i2.276 (3)C25—H250.9300
Sn2—C222.144 (5)C26—C271.3900
Sn2—C292.146 (5)C26—H260.9300
Sn2—C362.143 (5)C27—C281.3900
Sn2—O22.272 (3)C27—H270.9300
Sn2—O32.277 (4)C28—H280.9300
S1—C451.757 (6)C29—C301.499 (6)
S1—C441.784 (7)C29—H29A0.9700
S2—C451.651 (6)C29—H29B0.9700
S3—C531.748 (7)C30—C311.3900
S3—C521.787 (6)C30—C351.3900
S4—C531.668 (8)C31—C321.3900
O1—C431.239 (6)C31—H310.9300
O2—C431.270 (6)C32—C331.3900
O3—C511.236 (6)C32—H320.9300
O4—C511.268 (6)C33—C341.3900
O4—Sn1ii2.276 (3)C33—H330.9300
N1—C451.344 (6)C34—C351.3900
N1—C461.451 (7)C34—H340.9300
N1—C501.471 (7)C35—H350.9300
N2—C531.322 (7)C36—C371.507 (6)
N2—C541.445 (8)C36—H36A0.9700
N2—C581.462 (8)C36—H36B0.9700
C1—C21.505 (7)C37—C381.3900
C1—H1A0.9700C37—C421.3900
C1—H1B0.9700C38—C391.3900
C2—C31.3900C38—H380.9300
C2—C71.3900C39—C401.3900
C3—C41.3900C39—H390.9300
C3—H30.9300C40—C411.3900
C4—C51.3900C40—H400.9300
C4—H40.9300C41—C421.3900
C5—C61.3900C41—H410.9300
C5—H50.9300C42—H420.9300
C6—C71.3900C43—C441.505 (7)
C6—H60.9300C44—H44A0.9700
C7—H70.9300C44—H44B0.9700
C8—C91.493 (6)C46—C471.501 (5)
C8—H8A0.9700C46—H46A0.9700
C8—H8B0.9700C46—H46B0.9700
C9—C101.3900C47—C481.484 (5)
C9—C141.3900C47—H47A0.9700
C10—C111.3900C47—H47B0.9700
C10—H100.9300C48—C491.479 (5)
C11—C121.3900C48—H48A0.9700
C11—H110.9300C48—H48B0.9700
C12—C131.3900C49—C501.490 (5)
C12—H120.9300C49—H49A0.9700
C13—C141.3900C49—H49B0.9700
C13—H130.9300C50—H50A0.9700
C14—H140.9300C50—H50B0.9700
C15—C161.491 (6)C51—C521.496 (7)
C15—H15A0.9700C52—H52A0.9700
C15—H15B0.9700C52—H52B0.9700
C16—C171.3900C54—C551.491 (5)
C16—C211.3900C54—H54A0.9700
C17—C181.3900C54—H54B0.9700
C17—H170.9300C55—C561.491 (5)
C18—C191.3900C55—H55A0.9700
C18—H180.9300C55—H55B0.9700
C19—C201.3900C56—C571.493 (5)
C19—H190.9300C56—H56A0.9700
C20—C211.3900C56—H56B0.9700
C20—H200.9300C57—C581.483 (5)
C21—H210.9300C57—H57A0.9700
C22—C231.498 (7)C57—H57B0.9700
C22—H22A0.9700C58—H58A0.9700
C22—H22B0.9700C58—H58B0.9700
C23—C241.3900
C1—Sn1—C15114.1 (2)Sn2—C29—H29A107.0
C1—Sn1—C8117.9 (2)C30—C29—H29B107.0
C15—Sn1—C8127.4 (2)Sn2—C29—H29B107.0
C1—Sn1—O186.11 (19)H29A—C29—H29B106.7
C15—Sn1—O189.25 (19)C31—C30—C35120.0
C8—Sn1—O187.04 (18)C31—C30—C29118.8 (3)
C1—Sn1—O4i88.16 (19)C35—C30—C29121.2 (3)
C15—Sn1—O4i92.35 (18)C30—C31—C32120.0
C8—Sn1—O4i96.38 (18)C30—C31—H31120.0
O1—Sn1—O4i174.2 (1)C32—C31—H31120.0
C36—Sn2—C22115.6 (2)C31—C32—C33120.0
C36—Sn2—C29128.4 (2)C31—C32—H32120.0
C22—Sn2—C29115.3 (2)C33—C32—H32120.0
C36—Sn2—O291.43 (19)C34—C33—C32120.0
C22—Sn2—O289.20 (19)C34—C33—H33120.0
C29—Sn2—O297.31 (17)C32—C33—H33120.0
C36—Sn2—O389.8 (2)C33—C34—C35120.0
C22—Sn2—O385.38 (19)C33—C34—H34120.0
C29—Sn2—O386.15 (17)C35—C34—H34120.0
O2—Sn2—O3174.4 (1)C34—C35—C30120.0
C45—S1—C44103.2 (3)C34—C35—H35120.0
C53—S3—C52103.8 (4)C30—C35—H35120.0
C43—O1—Sn1126.5 (3)C37—C36—Sn2111.3 (3)
C43—O2—Sn2136.4 (3)C37—C36—H36A109.4
C51—O3—Sn2127.9 (3)Sn2—C36—H36A109.4
C51—O4—Sn1ii136.4 (3)C37—C36—H36B109.4
C45—N1—C46126.1 (6)Sn2—C36—H36B109.4
C45—N1—C50120.7 (6)H36A—C36—H36B108.0
C46—N1—C50110.9 (5)C38—C37—C42120.0
C53—N2—C54127.1 (6)C38—C37—C36119.6 (4)
C53—N2—C58122.9 (7)C42—C37—C36120.3 (4)
C54—N2—C58110.0 (7)C37—C38—C39120.0
C2—C1—Sn1113.6 (3)C37—C38—H38120.0
C2—C1—H1A108.8C39—C38—H38120.0
Sn1—C1—H1A108.8C38—C39—C40120.0
C2—C1—H1B108.8C38—C39—H39120.0
Sn1—C1—H1B108.8C40—C39—H39120.0
H1A—C1—H1B107.7C39—C40—C41120.0
C3—C2—C7120.0C39—C40—H40120.0
C3—C2—C1120.6 (4)C41—C40—H40120.0
C7—C2—C1119.4 (4)C42—C41—C40120.0
C2—C3—C4120.0C42—C41—H41120.0
C2—C3—H3120.0C40—C41—H41120.0
C4—C3—H3120.0C41—C42—C37120.0
C3—C4—C5120.0C41—C42—H42120.0
C3—C4—H4120.0C37—C42—H42120.0
C5—C4—H4120.0O1—C43—O2124.8 (5)
C6—C5—C4120.0O1—C43—C44117.9 (5)
C6—C5—H5120.0O2—C43—C44117.2 (5)
C4—C5—H5120.0C43—C44—S1116.9 (4)
C5—C6—C7120.0C43—C44—H44A108.1
C5—C6—H6120.0S1—C44—H44A108.1
C7—C6—H6120.0C43—C44—H44B108.1
C6—C7—C2120.0S1—C44—H44B108.1
C6—C7—H7120.0H44A—C44—H44B107.3
C2—C7—H7120.0N1—C45—S2125.0 (5)
C9—C8—Sn1119.7 (3)N1—C45—S1113.2 (5)
C9—C8—H8A107.4S2—C45—S1121.9 (3)
Sn1—C8—H8A107.4N1—C46—C47106.8 (7)
C9—C8—H8B107.4N1—C46—H46A110.4
Sn1—C8—H8B107.4C47—C46—H46A110.4
H8A—C8—H8B106.9N1—C46—H46B110.4
C10—C9—C14120.0C47—C46—H46B110.4
C10—C9—C8119.8 (4)H46A—C46—H46B108.6
C14—C9—C8120.2 (4)C48—C47—C46105.3 (4)
C11—C10—C9120.0C48—C47—H47A110.7
C11—C10—H10120.0C46—C47—H47A110.7
C9—C10—H10120.0C48—C47—H47B110.7
C10—C11—C12120.0C46—C47—H47B110.7
C10—C11—H11120.0H47A—C47—H47B108.8
C12—C11—H11120.0C49—C48—C47106.6 (5)
C13—C12—C11120.0C49—C48—H48A110.4
C13—C12—H12120.0C47—C48—H48A110.4
C11—C12—H12120.0C49—C48—H48B110.4
C14—C13—C12120.0C47—C48—H48B110.4
C14—C13—H13120.0H48A—C48—H48B108.6
C12—C13—H13120.0C48—C49—C50105.8 (4)
C13—C14—C9120.0C48—C49—H49A110.6
C13—C14—H14120.0C50—C49—H49A110.6
C9—C14—H14120.0C48—C49—H49B110.6
C16—C15—Sn1110.2 (3)C50—C49—H49B110.6
C16—C15—H15A109.6H49A—C49—H49B108.7
Sn1—C15—H15A109.6N1—C50—C49107.8 (5)
C16—C15—H15B109.6N1—C50—H50A110.1
Sn1—C15—H15B109.6C49—C50—H50A110.1
H15A—C15—H15B108.1N1—C50—H50B110.1
C17—C16—C21120.0C49—C50—H50B110.1
C17—C16—C15120.1 (4)H50A—C50—H50B108.5
C21—C16—C15119.9 (4)O3—C51—O4123.8 (4)
C18—C17—C16120.0O3—C51—C52119.3 (5)
C18—C17—H17120.0O4—C51—C52117.0 (4)
C16—C17—H17120.0C51—C52—S3115.8 (4)
C17—C18—C19120.0C51—C52—H52A108.3
C17—C18—H18120.0S3—C52—H52A108.3
C19—C18—H18120.0C51—C52—H52B108.3
C20—C19—C18120.0S3—C52—H52B108.3
C20—C19—H19120.0H52A—C52—H52B107.4
C18—C19—H19120.0N2—C53—S4125.4 (6)
C19—C20—C21120.0N2—C53—S3112.3 (6)
C19—C20—H20120.0S4—C53—S3122.3 (4)
C21—C20—H20120.0N2—C54—C55105.6 (7)
C20—C21—C16120.0N2—C54—H54A110.6
C20—C21—H21120.0C55—C54—H54A110.6
C16—C21—H21120.0N2—C54—H54B110.6
C23—C22—Sn2114.3 (3)C55—C54—H54B110.6
C23—C22—H22A108.7H54A—C54—H54B108.8
Sn2—C22—H22A108.7C54—C55—C56105.3 (4)
C23—C22—H22B108.7C54—C55—H55A110.7
Sn2—C22—H22B108.7C56—C55—H55A110.7
H22A—C22—H22B107.6C54—C55—H55B110.7
C24—C23—C28120.0C56—C55—H55B110.7
C24—C23—C22120.0 (3)H55A—C55—H55B108.8
C28—C23—C22119.9 (3)C55—C56—C57105.3 (4)
C25—C24—C23120.0C55—C56—H56A110.7
C25—C24—H24120.0C57—C56—H56A110.7
C23—C24—H24120.0C55—C56—H56B110.7
C24—C25—C26120.0C57—C56—H56B110.7
C24—C25—H25120.0H56A—C56—H56B108.8
C26—C25—H25120.0C58—C57—C56104.8 (4)
C27—C26—C25120.0C58—C57—H57A110.8
C27—C26—H26120.0C56—C57—H57A110.8
C25—C26—H26120.0C58—C57—H57B110.8
C26—C27—C28120.0C56—C57—H57B110.8
C26—C27—H27120.0H57A—C57—H57B108.9
C28—C27—H27120.0N2—C58—C57107.0 (7)
C27—C28—C23120.0N2—C58—H58A110.3
C27—C28—H28120.0C57—C58—H58A110.3
C23—C28—H28120.0N2—C58—H58B110.3
C30—C29—Sn2121.3 (3)C57—C58—H58B110.3
C30—C29—H29A107.0H58A—C58—H58B108.6
C1—Sn1—O1—C43178.3 (5)C29—Sn2—C36—C37−179.3 (3)
C15—Sn1—O1—C43−67.5 (5)O2—Sn2—C36—C3780.2 (4)
C8—Sn1—O1—C4360.0 (5)O3—Sn2—C36—C37−94.4 (4)
C36—Sn2—O2—C4366.6 (5)Sn2—C36—C37—C3874.1 (4)
C22—Sn2—O2—C43−177.8 (5)Sn2—C36—C37—C42−103.4 (4)
C29—Sn2—O2—C43−62.5 (5)C36—C37—C38—C39−177.6 (4)
C36—Sn2—O3—C51−69.4 (5)C36—C37—C42—C41177.5 (4)
C22—Sn2—O3—C51174.9 (5)Sn1—O1—C43—O23.2 (8)
C29—Sn2—O3—C5159.2 (5)Sn1—O1—C43—C44179.3 (4)
C15—Sn1—C1—C2−177.2 (3)Sn2—O2—C43—O1−178.1 (4)
C8—Sn1—C1—C2−5.2 (5)Sn2—O2—C43—C445.8 (8)
O1—Sn1—C1—C2−89.8 (4)O1—C43—C44—S16.2 (8)
O4i—Sn1—C1—C291.0 (4)O2—C43—C44—S1−177.4 (4)
Sn1—C1—C2—C3−108.5 (4)C45—S1—C44—C4381.4 (5)
Sn1—C1—C2—C770.4 (4)C46—N1—C45—S2172.9 (6)
C1—C2—C3—C4178.9 (4)C50—N1—C45—S211.4 (8)
C1—C2—C7—C6−178.9 (4)C46—N1—C45—S1−8.0 (8)
C1—Sn1—C8—C978.6 (5)C50—N1—C45—S1−169.5 (4)
C15—Sn1—C8—C9−110.6 (4)C44—S1—C45—N1−175.5 (4)
O1—Sn1—C8—C9162.6 (4)C44—S1—C45—S23.7 (5)
O4i—Sn1—C8—C9−12.7 (4)C45—N1—C46—C47−100.7 (7)
Sn1—C8—C9—C10−66.2 (5)C50—N1—C46—C4762.3 (8)
Sn1—C8—C9—C14113.8 (4)N1—C46—C47—C48−65.1 (8)
C8—C9—C10—C11180.0 (4)C46—C47—C48—C4969.7 (8)
C8—C9—C14—C13−180.0 (4)C47—C48—C49—C50−68.5 (7)
C1—Sn1—C15—C16−11.3 (4)C45—N1—C50—C49102.6 (7)
C8—Sn1—C15—C16177.6 (3)C46—N1—C50—C49−61.5 (7)
O1—Sn1—C15—C16−96.7 (4)C48—C49—C50—N162.7 (7)
O4i—Sn1—C15—C1677.7 (4)Sn2—O3—C51—O44.9 (7)
Sn1—C15—C16—C1771.6 (4)Sn2—O3—C51—C52−175.9 (4)
Sn1—C15—C16—C21−107.2 (3)Sn1ii—O4—C51—O3−176.3 (4)
C15—C16—C17—C18−178.7 (4)Sn1ii—O4—C51—C524.5 (8)
C15—C16—C21—C20178.7 (4)O3—C51—C52—S3−4.3 (8)
C36—Sn2—C22—C23−178.0 (4)O4—C51—C52—S3175.0 (4)
C29—Sn2—C22—C23−6.9 (5)C53—S3—C52—C5199.4 (6)
O2—Sn2—C22—C2390.8 (4)C54—N2—C53—S4−176.5 (8)
O3—Sn2—C22—C23−90.4 (4)C58—N2—C53—S44.0 (16)
Sn2—C22—C23—C24−110.2 (4)C54—N2—C53—S34.6 (14)
Sn2—C22—C23—C2865.8 (5)C58—N2—C53—S3−174.9 (8)
C22—C23—C24—C25175.9 (4)C52—S3—C53—N2178.2 (7)
C36—Sn2—C29—C30−107.8 (4)C52—S3—C53—S4−0.8 (7)
C22—Sn2—C29—C3082.4 (5)C53—N2—C54—C55115.4 (11)
O2—Sn2—C29—C30−10.1 (4)C58—N2—C54—C55−65.0 (10)
O3—Sn2—C29—C30165.5 (4)N2—C54—C55—C5666.8 (8)
Sn2—C29—C30—C31121.0 (3)C54—C55—C56—C57−70.3 (9)
Sn2—C29—C30—C35−57.1 (5)C55—C56—C57—C5869.0 (8)
C29—C30—C31—C32−178.1 (4)C53—N2—C58—C57−115.4 (10)
C29—C30—C35—C34178.1 (4)C54—N2—C58—C5765.0 (11)
C22—Sn2—C36—C37−9.6 (5)C56—C57—C58—N2−65.2 (10)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5336).

References

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