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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m832.
Published online 2008 May 21. doi:  10.1107/S1600536808014888
PMCID: PMC2961457

Tetra-n-butyl­ammonium iodido(pyrrolidine-1-carbodithio­ato-κ2 S,S′)(tris-tert-butoxy­silanethiol­ato-κS)cadmate(II)

Abstract

In the anion of the title compound, (C16H36N)[Cd(C5H8NS2)(C12H27O3SSi)I], the Cd atom is four-coordinated by S,S′-chelating dithio­carbamate, S–donating silanethiol­ate and iodide ligands in a distorted tetrahedral environment . Inter­molecular C—H(...) S and C—H(...)I inter­actions between cations and anions are present. Two C atoms of a tert-butyl group are disordered over two positions; the site occupancies are ca 0.65 and 0.35.

Related literature

For related literature, see: Allen (2002 [triangle]); Battaglia & Corradi (1986 [triangle]); Clemente et al. (1987 [triangle]); Kropidłowska et al. (2006a [triangle],b [triangle]); Kropidłowska, Chojnacki et al. (2008 [triangle]); Kropidłowska, Rotaru et al. (2008 [triangle]); Wojnowski et al. (1992 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m832-scheme1.jpg

Experimental

Crystal data

  • (C16H36N)[Cd(C5H8NS2)(C12H27O3SSi)I]
  • M r = 907.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m832-efi1.jpg
  • a = 14.8881 (9) Å
  • b = 16.3973 (9) Å
  • c = 18.6471 (11) Å
  • β = 105.519 (5)°
  • V = 4386.3 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.40 mm−1
  • T = 120 (2) K
  • 0.34 × 0.08 × 0.05 mm

Data collection

  • Oxford Diffraction KM-4-CCD diffractometer
  • Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006 [triangle]); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 [triangle])] T min = 0.744, T max = 0.943
  • 32652 measured reflections
  • 8628 independent reflections
  • 5398 reflections with I > 2σ(I)
  • R int = 0.065

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.088
  • S = 0.86
  • 8628 reflections
  • 423 parameters
  • H-atom parameters constrained
  • Δρmax = 1.01 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014888/sg2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014888/sg2247Isup2.hkl

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

Acknowledgments

The research was supported by the Polish Ministry of Education and Science (grant No. 1 T09 A 117 30). AK acknowledges financial support provided by the Foundation for Polish Science (FNP).

supplementary crystallographic information

Comment

The study of metal complexes with S-donor ligands is a well established field. Current interest in such systems stems from the fact that they may serve as potential precursors of metal sulfides. Our recent investigations are therefore focused on the synthesis of compounds with different S-donors (among them one with S—Si bond) ligating to the same metallic centre (Kropidłowska, Chojnacki, et al., 2008; Kropidłowska, Rotaru, et al., 2008). The synthesis and analysis of products obtained in [Cd{SSi(OtBu)3}2]2 (Wojnowski, et al., 1992) | (-)S2CNR2 (dtc) | R'4NX reaction system have so far proved, that besides the desired complexes with sulfur rich kernel (Kropidłowska, Chojnacki, et al., 2008) some other ionic compounds, e.g., (Et4N)[Cd(S2NEt2)2I] (Kropidłowska, et al., 2006a) or (Bu4N)2[CdBr4]×2C7H8 (Kropidłowska, et al., 2006b) may also be formed.

In the present paper we describe the product of a reaction between cadmium tri-tert-butoxysilanethiolate, ammonium 1-pyrrolidinylcarbodithioate and tetraethylammonium iodide carried out in toluene/propanol-2 mixture. Its crystal structure was determined, demonstrating that a new iodocadmate, [Cd{SSi(OtBu)3}(S2CNC4H9)I](-)[Et4N](+) (I), with additional silanethiolate and 1-pyrrolidinylcarbodithioate ligands was obtained. The molecular structure of I with atom numbering scheme is shown in Figure 1. The compound represents a novel type of complex with mixed S-donor ligands. Up to now structures (Allen, 2002) of only two similar compounds have been determined, namely for Pt(II) - FISMAV (Clemente et al., 1987) and Bi(III) - DUDWII (Battaglia & Corradi,1986) where dtc ligand and other S-donor (S-methyl dtc and thiourea respectively) are accompanied by a halogenide.

In the complex [Cd{SSi(OtBu)3}(S2CNC4H9)I](-) anion Cd atoms are four-coordinated in a CdS3I core. The arrangement of donor atoms can be primarily regarded as distorted (because of the presence of the chelating agent) tetrahedron with the widest S1—Cd1—S2 (124.78°) angle. Because of the distance (2.782 Å) the additional interaction between Cd1 and O2 is questionable (compare e.g. PAGBAA (Wojnowski et al., 1992)). A weak C—H···S interaction between cation and one of the dtc sulfur atoms (S3) can be assumed with d(H···S) 2.99Å (Table 1). What more, also C—H···I short contacts between iodine and some methylene groups from both dtc ligand and cation, with d(H···I) 3.16Å and 3.15Å respectively, may be taken into account (Figure 2). It is worthy to note, that in the unit cell of I cations and anions are arranged in the form of alternating layers (Figure 3).

It is hard to state how iodide ligand enters cadmium coordination sphere. Most probably species possessing both S-donors undergo this reaction. Related investigations are now in progress.

Experimental

Ammonium 1-pyrrolidinylcarbodithioate (0.029 g, 0.177 mmol) and equimolar amount of tetra-n-butylammoniumiodide (0.066 g, 0.178 mmol) were dissolved in 15 cm3 of toluene/propanol-2 (5:1, v/v) mixture. Next, cadmium tri-tert-butoxysilanethiolate (0.11 g, 0.089 mmol, (Wojnowski et al., 1992)) was dissolved in 5 cm3of hot toluene/propanol-2 mixture and the solution was added to dithiocarbamate solution. The reagents were stirred and heated under reflux for 4 h under argon and then left for decantation. Clear solution was drained to a Schlenk tube and left at 5°C to crystallize the products. After a week needle-like crystals were collected.

Refinement

All H atoms were placed in calculated positions and refined as riding on their carrier atoms with respective Uiso(H) values: C—H = 0.98 Å (CH3) and Uiso(H) = 1.5 Ueq(C), C—H = 0.99 Å (CH2) and Uĩso(H) = 1.2 Ueq(C). Atoms C32 and C33 within one of n-butyl groups (C30—C33) are disordered over two positions with probabilities 0.65/0.35.

Figures

Fig. 1.
Molecular structure and atom-numbering scheme for [Cd{SSi(OtBu)3}(S2CNC4H9)I](-)[Et4N](+) (I) with displacement ellipsoids drawn at 50% probability level. Atoms C32 and C33 are disordered over two positions - only major set is shown. H atoms have been ...
Fig. 2.
Interactions and short contacts present within the unit cell of I - view along the a axis.
Fig. 3.
The network of interactions in the crystal lattice of I view along the a axis.
Fig. 4.
The crystal lattice of I. Color codes: blue-cations; green - anions.

Crystal data

(C16H36N)[Cd(C5H8NS2)(C12H27O3SSi)I]Z = 4
Mr = 907.49F000 = 1880
Monoclinic, P21/cDx = 1.374 Mg m3
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 14.8881 (9) Åθ = 2.5–32.6º
b = 16.3973 (9) ŵ = 1.40 mm1
c = 18.6471 (11) ÅT = 120 (2) K
β = 105.519 (5)ºNeedle, colourless
V = 4386.3 (5) Å30.34 × 0.08 × 0.05 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer8628 independent reflections
Monochromator: graphite5398 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.065
T = 120(2) Kθmax = 26º
ω scansθmin = 2.4º
Absorption correction: analytical[CrysAlis RED (Oxford Diffraction, 2006); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]h = −17→18
Tmin = 0.744, Tmax = 0.943k = −20→19
32652 measured reflectionsl = −22→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0471P)2] where P = (Fo2 + 2Fc2)/3
S = 0.86(Δ/σ)max = 0.002
8628 reflectionsΔρmax = 1.01 e Å3
423 parametersΔρmin = −0.44 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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*/UeqOcc. (<1)
Cd10.30998 (2)0.104413 (19)0.278712 (17)0.02783 (9)
N10.3153 (2)0.3675 (2)0.29473 (19)0.0284 (9)
O10.14159 (19)−0.11475 (17)0.31904 (16)0.0316 (7)
O20.1439 (2)0.01702 (18)0.23839 (16)0.0334 (7)
O30.0676 (2)0.01545 (18)0.35510 (16)0.0337 (7)
S20.22367 (8)0.23808 (7)0.22960 (6)0.0290 (3)
S10.28545 (8)0.02356 (7)0.38426 (6)0.0299 (3)
S30.41572 (8)0.23419 (7)0.33244 (6)0.0301 (3)
Si10.15373 (8)−0.01594 (8)0.32351 (7)0.0288 (3)
I10.39336 (2)0.034354 (18)0.179160 (17)0.03680 (10)
C10.1167 (3)−0.1721 (3)0.3691 (3)0.0353 (11)
C20.1662 (4)−0.1504 (3)0.4499 (3)0.0458 (13)
H2A0.2331−0.14420.45530.069*
H2B0.1561−0.1940.48280.069*
H2C0.1409−0.09910.46330.069*
C30.1497 (4)−0.2547 (3)0.3498 (3)0.0466 (13)
H3A0.1195−0.26730.29750.07*
H3B0.1334−0.29660.38170.07*
H3C0.2175−0.25360.35770.07*
C40.0115 (3)−0.1730 (3)0.3562 (3)0.0487 (14)
H4A−0.0101−0.11810.3640.073*
H4B−0.0051−0.2110.39110.073*
H4C−0.0181−0.19050.3050.073*
C50.0752 (3)−0.0009 (3)0.1681 (3)0.0376 (12)
C6−0.0197 (4)−0.0133 (5)0.1797 (3)0.074 (2)
H6A−0.0206−0.06450.20670.111*
H6B−0.0661−0.0160.13130.111*
H6C−0.03440.03220.20860.111*
C70.1083 (4)−0.0747 (4)0.1348 (3)0.0630 (17)
H7A0.1736−0.06720.13490.094*
H7B0.0701−0.08210.08360.094*
H7C0.1027−0.1230.16430.094*
C80.0763 (5)0.0739 (4)0.1197 (3)0.076 (2)
H8A0.05580.12180.14240.114*
H8B0.03410.0650.07010.114*
H8C0.13970.0830.11530.114*
C90.0421 (3)0.0913 (3)0.3841 (2)0.0337 (11)
C100.0733 (4)0.1643 (3)0.3458 (3)0.0437 (13)
H10A0.14150.16550.35790.066*
H10B0.05080.21480.36320.066*
H10C0.04760.15960.29180.066*
C110.0879 (3)0.0931 (3)0.4676 (2)0.0427 (13)
H11A0.06570.04680.49140.064*
H11B0.07180.14420.48850.064*
H11C0.15580.08960.47660.064*
C12−0.0637 (3)0.0905 (3)0.3688 (3)0.0479 (14)
H12A−0.09220.09380.3150.072*
H12B−0.08370.13730.39330.072*
H12C−0.08340.03990.38810.072*
C130.3184 (3)0.2873 (3)0.2869 (2)0.0261 (10)
C140.2327 (3)0.4177 (3)0.2626 (3)0.0347 (11)
H14A0.17610.39290.27150.042*
H14B0.22320.42470.20830.042*
C150.2549 (3)0.4988 (3)0.3030 (3)0.0487 (14)
H15A0.22520.54460.27070.058*
H15B0.23360.49940.34890.058*
C160.3595 (3)0.5039 (3)0.3208 (3)0.0474 (14)
H16A0.38450.54080.36350.057*
H16B0.37950.52390.27740.057*
C170.3925 (3)0.4161 (3)0.3402 (3)0.0349 (11)
H17A0.45120.4050.32660.042*
H17B0.40210.40490.39390.042*
N20.4647 (2)0.19938 (19)0.59242 (18)0.0249 (8)
C180.4401 (3)0.1098 (2)0.5800 (2)0.0289 (10)
H18A0.49860.0780.58920.035*
H18B0.40570.10190.52720.035*
C190.3819 (3)0.0751 (3)0.6284 (3)0.0341 (11)
H19A0.32980.11270.62810.041*
H19B0.42080.06990.68030.041*
C200.3430 (3)−0.0091 (3)0.5992 (3)0.0338 (11)
H20A0.3051−0.03020.63140.041*
H20B0.3011−0.00240.54840.041*
C210.4168 (3)−0.0712 (3)0.5966 (3)0.0421 (12)
H21A0.4612−0.07550.64580.063*
H21B0.4497−0.05420.56010.063*
H21C0.3873−0.12440.58220.063*
C220.5240 (3)0.2197 (2)0.5404 (2)0.0277 (10)
H22A0.57570.17980.5490.033*
H22B0.48550.21210.48860.033*
C230.5655 (3)0.3042 (3)0.5468 (2)0.0332 (11)
H23A0.60560.31280.59790.04*
H23B0.51490.34520.53730.04*
C240.6231 (3)0.3158 (3)0.4912 (2)0.0357 (11)
H24A0.6690.27080.49730.043*
H24B0.58140.31230.44010.043*
C250.6744 (4)0.3961 (3)0.4999 (3)0.0544 (15)
H25A0.72050.39770.54850.082*
H25B0.62990.44090.49650.082*
H25C0.7060.40180.46040.082*
C260.5175 (3)0.2158 (3)0.6728 (2)0.0271 (10)
H26A0.47720.19980.70490.033*
H26B0.52840.27520.67890.033*
C270.6106 (3)0.1726 (3)0.7009 (2)0.0327 (11)
H27A0.65190.18730.66930.039*
H27B0.60080.11280.69770.039*
C280.6570 (4)0.1966 (3)0.7818 (3)0.0413 (12)
H28A0.61270.18620.81190.05*
H28B0.7120.16120.80120.05*
C290.6878 (4)0.2841 (3)0.7919 (3)0.0500 (14)
H29A0.63290.31970.78130.075*
H29B0.72560.2970.75770.075*
H29C0.72490.29270.84330.075*
C300.3781 (3)0.2521 (3)0.5773 (3)0.0354 (11)
H30A0.34680.24220.61720.042*
H30B0.39760.310.58060.042*
C310.3079 (4)0.2388 (3)0.5032 (3)0.0605 (16)
H31A0.2880.1810.49750.073*
H31B0.33510.25330.46190.073*
C320.2223 (7)0.2961 (6)0.5028 (6)0.043 (2)0.646 (11)
H32A0.16470.27310.46930.052*0.646 (11)
H32B0.21370.29940.55350.052*0.646 (11)
C330.2390 (6)0.3765 (7)0.4776 (5)0.057 (3)0.646 (11)
H33A0.2460.37310.42690.086*0.646 (11)
H33B0.29620.39890.51080.086*0.646 (11)
H33C0.18630.41210.47810.086*0.646 (11)
C32A0.2498 (10)0.3141 (12)0.4648 (9)0.043 (2)0.354 (11)
H32C0.28910.36320.46720.052*0.354 (11)
H32D0.21630.30260.41230.052*0.354 (11)
C33A0.1826 (15)0.3225 (15)0.5139 (10)0.064 (6)0.354 (11)
H33D0.14080.36880.49680.097*0.354 (11)
H33E0.21840.33160.56560.097*0.354 (11)
H33F0.14580.27240.51090.097*0.354 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.03032 (19)0.02514 (18)0.02964 (18)−0.00049 (15)0.01080 (14)0.00300 (14)
N10.027 (2)0.027 (2)0.031 (2)0.0019 (17)0.0088 (17)0.0000 (16)
O10.0297 (17)0.0344 (18)0.0331 (18)−0.0072 (14)0.0127 (14)−0.0026 (14)
O20.0301 (17)0.044 (2)0.0260 (17)−0.0020 (15)0.0079 (14)0.0019 (14)
O30.0327 (18)0.0352 (19)0.0368 (18)−0.0021 (14)0.0157 (14)−0.0017 (14)
S20.0277 (6)0.0257 (6)0.0322 (6)0.0001 (5)0.0053 (5)0.0009 (5)
S10.0329 (6)0.0317 (7)0.0246 (6)−0.0063 (5)0.0067 (5)0.0031 (5)
S30.0291 (6)0.0280 (6)0.0304 (6)−0.0029 (5)0.0032 (5)0.0043 (5)
Si10.0270 (7)0.0339 (8)0.0271 (7)−0.0037 (6)0.0098 (5)0.0004 (5)
I10.0454 (2)0.02957 (17)0.04242 (19)0.00608 (15)0.02381 (15)0.00383 (14)
C10.041 (3)0.025 (3)0.044 (3)−0.005 (2)0.018 (2)0.004 (2)
C20.056 (3)0.040 (3)0.045 (3)−0.005 (3)0.019 (3)0.009 (2)
C30.045 (3)0.040 (3)0.057 (3)−0.009 (3)0.018 (3)−0.004 (3)
C40.039 (3)0.041 (3)0.075 (4)−0.009 (2)0.029 (3)0.001 (3)
C50.030 (3)0.049 (3)0.030 (3)−0.001 (2)0.002 (2)−0.002 (2)
C60.034 (3)0.142 (6)0.045 (3)−0.011 (4)0.007 (3)−0.019 (4)
C70.062 (4)0.072 (4)0.048 (4)0.007 (3)0.002 (3)−0.024 (3)
C80.084 (5)0.087 (5)0.041 (4)−0.001 (4)−0.013 (3)0.015 (3)
C90.033 (3)0.039 (3)0.035 (3)0.003 (2)0.018 (2)−0.004 (2)
C100.056 (3)0.034 (3)0.046 (3)0.006 (3)0.023 (3)0.000 (2)
C110.048 (3)0.047 (3)0.037 (3)−0.001 (3)0.019 (2)0.001 (2)
C120.047 (3)0.052 (3)0.047 (3)−0.005 (3)0.017 (3)−0.010 (3)
C130.030 (2)0.024 (2)0.030 (2)−0.0016 (19)0.017 (2)0.0008 (19)
C140.034 (3)0.028 (3)0.045 (3)0.001 (2)0.015 (2)−0.001 (2)
C150.046 (3)0.036 (3)0.066 (4)0.001 (2)0.018 (3)−0.007 (3)
C160.047 (3)0.035 (3)0.065 (4)−0.002 (2)0.024 (3)−0.012 (3)
C170.033 (3)0.034 (3)0.041 (3)−0.005 (2)0.015 (2)−0.007 (2)
N20.030 (2)0.0176 (19)0.028 (2)−0.0002 (15)0.0099 (16)−0.0040 (15)
C180.036 (3)0.019 (2)0.032 (3)−0.004 (2)0.011 (2)−0.0033 (19)
C190.041 (3)0.030 (3)0.037 (3)−0.003 (2)0.021 (2)−0.002 (2)
C200.037 (3)0.033 (3)0.032 (3)−0.003 (2)0.012 (2)0.002 (2)
C210.047 (3)0.032 (3)0.050 (3)−0.003 (2)0.017 (3)−0.004 (2)
C220.038 (3)0.027 (2)0.020 (2)−0.002 (2)0.011 (2)−0.0016 (18)
C230.045 (3)0.025 (3)0.029 (3)−0.004 (2)0.009 (2)0.0035 (19)
C240.038 (3)0.038 (3)0.030 (3)−0.006 (2)0.007 (2)0.004 (2)
C250.068 (4)0.050 (3)0.048 (3)−0.022 (3)0.020 (3)0.007 (3)
C260.037 (3)0.027 (2)0.022 (2)−0.004 (2)0.015 (2)−0.0053 (19)
C270.044 (3)0.021 (2)0.035 (3)0.001 (2)0.015 (2)0.002 (2)
C280.046 (3)0.041 (3)0.035 (3)−0.001 (2)0.006 (2)−0.002 (2)
C290.056 (4)0.050 (3)0.040 (3)−0.006 (3)0.008 (3)−0.012 (2)
C300.039 (3)0.025 (3)0.045 (3)0.001 (2)0.015 (2)−0.007 (2)
C310.047 (3)0.045 (3)0.078 (4)0.014 (3)−0.003 (3)−0.017 (3)
C320.035 (5)0.057 (6)0.042 (6)0.006 (4)0.018 (4)−0.008 (4)
C330.048 (6)0.075 (9)0.045 (5)−0.002 (5)0.006 (4)0.005 (5)
C32A0.035 (5)0.057 (6)0.042 (6)0.006 (4)0.018 (4)−0.008 (4)
C33A0.061 (14)0.098 (17)0.041 (10)0.006 (12)0.025 (10)−0.014 (10)

Geometric parameters (Å, °)

Cd1—S12.4798 (11)C17—H17A0.99
Cd1—S22.5815 (11)C17—H17B0.99
Cd1—S32.6770 (11)N2—C221.513 (5)
Cd1—I12.7459 (4)N2—C301.516 (5)
N1—C131.326 (5)N2—C181.517 (5)
N1—C141.467 (5)N2—C261.518 (5)
N1—C171.468 (5)C18—C191.518 (6)
O1—C11.441 (5)C18—H18A0.99
O1—Si11.630 (3)C18—H18B0.99
O2—C51.460 (5)C19—C201.539 (6)
O2—Si11.646 (3)C19—H19A0.99
O3—C91.446 (5)C19—H19B0.99
O3—Si11.631 (3)C20—C211.509 (6)
S2—C131.726 (4)C20—H20A0.99
S1—Si12.0880 (16)C20—H20B0.99
S3—C131.709 (4)C21—H21A0.98
C1—C31.517 (6)C21—H21B0.98
C1—C41.519 (6)C21—H21C0.98
C1—C21.532 (6)C22—C231.509 (6)
C2—H2A0.98C22—H22A0.99
C2—H2B0.98C22—H22B0.99
C2—H2C0.98C23—C241.524 (6)
C3—H3A0.98C23—H23A0.99
C3—H3B0.98C23—H23B0.99
C3—H3C0.98C24—C251.509 (6)
C4—H4A0.98C24—H24A0.99
C4—H4B0.98C24—H24B0.99
C4—H4C0.98C25—H25A0.98
C5—C61.500 (7)C25—H25B0.98
C5—C71.503 (7)C25—H25C0.98
C5—C81.526 (7)C26—C271.519 (6)
C6—H6A0.98C26—H26A0.99
C6—H6B0.98C26—H26B0.99
C6—H6C0.98C27—C281.532 (6)
C7—H7A0.98C27—H27A0.99
C7—H7B0.98C27—H27B0.99
C7—H7C0.98C28—C291.502 (7)
C8—H8A0.98C28—H28A0.99
C8—H8B0.98C28—H28B0.99
C8—H8C0.98C29—H29A0.98
C9—C121.524 (6)C29—H29B0.98
C9—C111.525 (6)C29—H29C0.98
C9—C101.529 (6)C30—C311.510 (7)
C10—H10A0.98C30—H30A0.99
C10—H10B0.98C30—H30B0.99
C10—H10C0.98C31—C32A1.566 (18)
C11—H11A0.98C31—C321.581 (10)
C11—H11B0.98C31—H31A0.99
C11—H11C0.98C31—H31B0.99
C12—H12A0.98C32—C331.444 (14)
C12—H12B0.98C32—H32A0.99
C12—H12C0.98C32—H32B0.99
C14—C151.521 (6)C33—H33A0.98
C14—H14A0.99C33—H33B0.98
C14—H14B0.99C33—H33C0.98
C15—C161.505 (7)C32A—C33A1.53 (2)
C15—H15A0.99C32A—H32C0.99
C15—H15B0.99C32A—H32D0.99
C16—C171.533 (6)C33A—H33D0.98
C16—H16A0.99C33A—H33E0.98
C16—H16B0.99C33A—H33F0.98
S1—Cd1—S2124.78 (4)C16—C17—H17A111.2
S1—Cd1—S3108.95 (4)N1—C17—H17B111.2
S2—Cd1—S369.20 (3)C16—C17—H17B111.2
S1—Cd1—I1120.14 (3)H17A—C17—H17B109.1
S2—Cd1—I1112.80 (3)C22—N2—C30111.6 (3)
S3—Cd1—I1104.99 (3)C22—N2—C18105.9 (3)
C13—N1—C14124.2 (4)C30—N2—C18111.4 (3)
C13—N1—C17123.8 (4)C22—N2—C26110.9 (3)
C14—N1—C17111.9 (3)C30—N2—C26105.8 (3)
C1—O1—Si1131.3 (3)C18—N2—C26111.2 (3)
C5—O2—Si1131.3 (3)N2—C18—C19115.2 (3)
C9—O3—Si1135.8 (3)N2—C18—H18A108.5
C13—S2—Cd186.03 (14)C19—C18—H18A108.5
Si1—S1—Cd192.96 (5)N2—C18—H18B108.5
C13—S3—Cd183.34 (14)C19—C18—H18B108.5
O1—Si1—O3104.18 (15)H18A—C18—H18B107.5
O1—Si1—O2107.28 (16)C18—C19—C20110.3 (4)
O3—Si1—O2111.67 (16)C18—C19—H19A109.6
O1—Si1—S1114.29 (12)C20—C19—H19A109.6
O3—Si1—S1114.92 (12)C18—C19—H19B109.6
O2—Si1—S1104.45 (12)C20—C19—H19B109.6
O1—C1—C3105.9 (4)H19A—C19—H19B108.1
O1—C1—C4109.7 (4)C21—C20—C19114.1 (4)
C3—C1—C4109.8 (4)C21—C20—H20A108.7
O1—C1—C2110.3 (4)C19—C20—H20A108.7
C3—C1—C2109.8 (4)C21—C20—H20B108.7
C4—C1—C2111.2 (4)C19—C20—H20B108.7
C1—C2—H2A109.5H20A—C20—H20B107.6
C1—C2—H2B109.5C20—C21—H21A109.5
H2A—C2—H2B109.5C20—C21—H21B109.5
C1—C2—H2C109.5H21A—C21—H21B109.5
H2A—C2—H2C109.5C20—C21—H21C109.5
H2B—C2—H2C109.5H21A—C21—H21C109.5
C1—C3—H3A109.5H21B—C21—H21C109.5
C1—C3—H3B109.5C23—C22—N2116.6 (3)
H3A—C3—H3B109.5C23—C22—H22A108.1
C1—C3—H3C109.5N2—C22—H22A108.1
H3A—C3—H3C109.5C23—C22—H22B108.1
H3B—C3—H3C109.5N2—C22—H22B108.1
C1—C4—H4A109.5H22A—C22—H22B107.3
C1—C4—H4B109.5C22—C23—C24110.7 (4)
H4A—C4—H4B109.5C22—C23—H23A109.5
C1—C4—H4C109.5C24—C23—H23A109.5
H4A—C4—H4C109.5C22—C23—H23B109.5
H4B—C4—H4C109.5C24—C23—H23B109.5
O2—C5—C6111.1 (4)H23A—C23—H23B108.1
O2—C5—C7107.7 (4)C25—C24—C23113.3 (4)
C6—C5—C7112.0 (5)C25—C24—H24A108.9
O2—C5—C8104.7 (4)C23—C24—H24A108.9
C6—C5—C8110.8 (5)C25—C24—H24B108.9
C7—C5—C8110.2 (5)C23—C24—H24B108.9
C5—C6—H6A109.5H24A—C24—H24B107.7
C5—C6—H6B109.5C24—C25—H25A109.5
H6A—C6—H6B109.5C24—C25—H25B109.5
C5—C6—H6C109.5H25A—C25—H25B109.5
H6A—C6—H6C109.5C24—C25—H25C109.5
H6B—C6—H6C109.5H25A—C25—H25C109.5
C5—C7—H7A109.5H25B—C25—H25C109.5
C5—C7—H7B109.5N2—C26—C27116.2 (3)
H7A—C7—H7B109.5N2—C26—H26A108.2
C5—C7—H7C109.5C27—C26—H26A108.2
H7A—C7—H7C109.5N2—C26—H26B108.2
H7B—C7—H7C109.5C27—C26—H26B108.2
C5—C8—H8A109.5H26A—C26—H26B107.4
C5—C8—H8B109.5C26—C27—C28110.5 (4)
H8A—C8—H8B109.5C26—C27—H27A109.6
C5—C8—H8C109.5C28—C27—H27A109.6
H8A—C8—H8C109.5C26—C27—H27B109.6
H8B—C8—H8C109.5C28—C27—H27B109.6
O3—C9—C12106.5 (4)H27A—C27—H27B108.1
O3—C9—C11108.0 (4)C29—C28—C27114.3 (4)
C12—C9—C11110.4 (4)C29—C28—H28A108.7
O3—C9—C10110.9 (3)C27—C28—H28A108.7
C12—C9—C10110.3 (4)C29—C28—H28B108.7
C11—C9—C10110.6 (4)C27—C28—H28B108.7
C9—C10—H10A109.5H28A—C28—H28B107.6
C9—C10—H10B109.5C28—C29—H29A109.5
H10A—C10—H10B109.5C28—C29—H29B109.5
C9—C10—H10C109.5H29A—C29—H29B109.5
H10A—C10—H10C109.5C28—C29—H29C109.5
H10B—C10—H10C109.5H29A—C29—H29C109.5
C9—C11—H11A109.5H29B—C29—H29C109.5
C9—C11—H11B109.5C31—C30—N2115.7 (4)
H11A—C11—H11B109.5C31—C30—H30A108.4
C9—C11—H11C109.5N2—C30—H30A108.4
H11A—C11—H11C109.5C31—C30—H30B108.4
H11B—C11—H11C109.5N2—C30—H30B108.4
C9—C12—H12A109.5H30A—C30—H30B107.4
C9—C12—H12B109.5C30—C31—C32A117.8 (8)
H12A—C12—H12B109.5C30—C31—C32106.1 (5)
C9—C12—H12C109.5C30—C31—H31A110.5
H12A—C12—H12C109.5C32A—C31—H31A126.3
H12B—C12—H12C109.5C32—C31—H31A110.5
N1—C13—S3120.1 (3)C30—C31—H31B110.5
N1—C13—S2119.0 (3)C32A—C31—H31B75.3
S3—C13—S2120.9 (2)C32—C31—H31B110.5
N1—C14—C15103.9 (4)H31A—C31—H31B108.7
N1—C14—H14A111C33—C32—C31109.6 (9)
C15—C14—H14A111C33—C32—H32A109.8
N1—C14—H14B111C31—C32—H32A109.8
C15—C14—H14B111C33—C32—H32B109.8
H14A—C14—H14B109C31—C32—H32B109.8
C16—C15—C14103.5 (4)H32A—C32—H32B108.2
C16—C15—H15A111.1C33A—C32A—C3199.6 (14)
C14—C15—H15A111.1C33A—C32A—H32C111.9
C16—C15—H15B111.1C31—C32A—H32C111.9
C14—C15—H15B111.1C33A—C32A—H32D111.9
H15A—C15—H15B109C31—C32A—H32D111.9
C15—C16—C17104.4 (4)H32C—C32A—H32D109.6
C15—C16—H16A110.9C32A—C33A—H33D109.5
C17—C16—H16A110.9C32A—C33A—H33E109.5
C15—C16—H16B110.9H33D—C33A—H33E109.5
C17—C16—H16B110.9C32A—C33A—H33F109.5
H16A—C16—H16B108.9H33D—C33A—H33F109.5
N1—C17—C16102.8 (4)H33E—C33A—H33F109.5
N1—C17—H17A111.2
S1—Cd1—S2—C1394.76 (14)Cd1—S3—C13—S2−7.3 (2)
S3—Cd1—S2—C13−4.40 (14)Cd1—S2—C13—N1−173.1 (3)
I1—Cd1—S2—C13−102.47 (14)Cd1—S2—C13—S37.5 (2)
S2—Cd1—S1—Si171.18 (6)C13—N1—C14—C15165.6 (4)
S3—Cd1—S1—Si1148.54 (5)C17—N1—C14—C15−11.2 (5)
I1—Cd1—S1—Si1−90.42 (5)N1—C14—C15—C1629.8 (5)
S1—Cd1—S3—C13−116.52 (14)C14—C15—C16—C17−37.3 (5)
S2—Cd1—S3—C134.46 (14)C13—N1—C17—C16171.6 (4)
I1—Cd1—S3—C13113.57 (14)C14—N1—C17—C16−11.6 (5)
C1—O1—Si1—O3−40.7 (4)C15—C16—C17—N130.1 (5)
C1—O1—Si1—O2−159.2 (3)C22—N2—C18—C19178.6 (4)
C1—O1—Si1—S185.6 (4)C30—N2—C18—C19−59.8 (5)
C9—O3—Si1—O1168.0 (4)C26—N2—C18—C1958.0 (5)
C9—O3—Si1—O2−76.5 (4)N2—C18—C19—C20167.2 (4)
C9—O3—Si1—S142.2 (4)C18—C19—C20—C2158.8 (5)
C5—O2—Si1—O147.7 (4)C30—N2—C22—C2363.9 (5)
C5—O2—Si1—O3−65.9 (4)C18—N2—C22—C23−174.6 (4)
C5—O2—Si1—S1169.4 (3)C26—N2—C22—C23−53.8 (5)
Cd1—S1—Si1—O1123.88 (12)N2—C22—C23—C24−180.0 (4)
Cd1—S1—Si1—O3−115.73 (13)C22—C23—C24—C25−174.2 (4)
Cd1—S1—Si1—O26.96 (13)C22—N2—C26—C27−56.0 (4)
Si1—O1—C1—C3−160.4 (3)C30—N2—C26—C27−177.3 (4)
Si1—O1—C1—C481.2 (5)C18—N2—C26—C2761.6 (4)
Si1—O1—C1—C2−41.6 (5)N2—C26—C27—C28178.3 (4)
Si1—O2—C5—C634.7 (6)C26—C27—C28—C29−67.5 (5)
Si1—O2—C5—C7−88.3 (5)C22—N2—C30—C3166.4 (5)
Si1—O2—C5—C8154.3 (4)C18—N2—C30—C31−51.9 (5)
Si1—O3—C9—C12153.6 (3)C26—N2—C30—C31−172.9 (4)
Si1—O3—C9—C11−87.8 (5)N2—C30—C31—C32A−147.3 (7)
Si1—O3—C9—C1033.6 (6)N2—C30—C31—C32176.6 (5)
C14—N1—C13—S3−175.3 (3)C30—C31—C32—C3385.9 (8)
C17—N1—C13—S31.2 (5)C32A—C31—C32—C33−29.8 (12)
C14—N1—C13—S25.4 (5)C30—C31—C32A—C33A−74.3 (14)
C17—N1—C13—S2−178.2 (3)C32—C31—C32A—C33A4.1 (11)
Cd1—S3—C13—N1173.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H17A···I1i0.993.163.830 (4)126
C30—H30B···I1ii0.993.153.960 (4)139
C31—H31B···S30.992.993.931 (7)160

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2247).

References

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