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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1064.
Published online 2010 August 11. doi:  10.1107/S160053681003076X
PMCID: PMC3008140

Tris(2-chloro­benz­yl)(1H-1,2,4-triazole-5-thiol­ato-κS)tin(IV)–tris­(2-chloro­benz­yl)(4H-1,2,4-triazole-3-thiol­ato-κS)tin(IV) (1/1)

Abstract

Tris(2-chloro­benz­yl)tin hydroxide condenses with 3-mercapto-1,2,4-triazole to form the 1:1 cocrystal of the title compound, [Sn(C7H6Cl)3(C2H2N3S)]. The asymmetric unit contains two mol­ecules which differ only in the position of the nitro­gen-bound H atom of the triazole ring; one mol­ecule is linked to the other mol­ecule by an N—H(...)N hydrogen bond. In the second mol­ecule, two of the chloro­benzyl units are disordered over two positions in a 0.73 (1):0.27 (1) ratio. The Sn atom in both mol­ecules shows a distorted tetra­hedral SnSC3 coordination.

Related literature

For comparison crystal structures, see: Aziz-ur-Rehman et al. (2006 [triangle]); Ma et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1064-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H6Cl)3(C2H2N3S)]
  • M r = 595.52
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1064-efi1.jpg
  • a = 9.696 (6) Å
  • b = 11.385 (5) Å
  • c = 23.670 (11) Å
  • α = 83.06 (2)°
  • β = 79.200 (18)°
  • γ = 68.559 (18)°
  • V = 2385 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.51 mm−1
  • T = 100 K
  • 0.35 × 0.25 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.620, T max = 0.805
  • 22480 measured reflections
  • 10780 independent reflections
  • 9232 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.091
  • S = 1.01
  • 10780 reflections
  • 560 parameters
  • 104 restraints
  • H-atom parameters constrained
  • Δρmax = 1.41 e Å−3
  • Δρmin = −0.81 e Å−3

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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003076X/xu5006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003076X/xu5006Isup2.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

Triorganotin(IV) derivatives of thiols generally exists as tetrahedral molecules because the sulfidelinkage lowers the Lewis acidity of tin; for 1,2,4-triazolyl-3-thiolates, however, the nitrogen sites sometimes engage in intermolecular coordination and polymeric compounds are generated. Among the triorganotin 1,2,4-triazolyl-3-thiolates, only carbon- and nitrogen-substituted derivatives have been characterized by crystal structure analysis, e.g., polymeric 4-methyl-1,2,4-triazole-3-thiolato)trimethyltin (Aziz-ur-Rehman et al., 2006) and monomeric (4-methyl-5-trifluoromethyl-1,2,4-triazole-3-thiolato)triphenyltin (Ma et al., 2007). 3-Mercapto-1,2,4-triazole itself has a nitrogen-bound hydrogen atom. It its condensation with tris(2-chlorobenzyl)tin hydroxide, the resulting product retains this hydrogen atom in the heterocyclic portion. The product is, in fact, a 1:1 co-crystal oftris(2-chlorobenzyl)(1,2,4-triazole-5-thiolato)tin(IV)–tris(2-\ chlorobenzyl)(1,3,4-triazole-2-thiolato)tin (Scheme I). The two molecular components are isoelectronic but differ only in the position of the nitrogen-bound hydrogen atom of the triazolyl ring. The tin atom in the two molecules show tetrahedral coordination. The first component (Fig. 1) is linked to the second component (Fig. 2) by an N–H···N hydrogen bond.

Experimental

Tris(2-chlorobenzyl)tin hydroxide (0.5 g, 1 mmol) and 3-mercapto-1,2,4-triazole (0.1 g, 1 mmol) were dissolved in 50 m of ethanol. The solution was heated for 2 h. Colorless crystals separated from the filtered solution after several days.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

For the heterocyclic ring in the first independent molecule, the amino H-atom was placed on the N2 atom as both the N1 and N3 atoms were within 2.8 Å of their symmetry-generated equivalents. The N2 atom forms a hydrogen bond to the N5 atom of the other independent molecule. For the heterocylic ring in the second independent molecule, a hydrogen atom placed on the N4 atom would be too close to the H23 atom of another molecule. Since the N5 atom is already an acceptor site, the N6 atom would then be the protonated atom. The N–H distances were set to 0.86 Å; the temperature factors were tied to those of the parent atoms.

The positioning of the amino H-atoms gives rise to different names for the two molecular species.

For the second molecule, two chlorobenzyl substitutents are disordered; the occupancies of the two could not be separately refined, and were assumed to be identical. The aromatic ring were refined as rigid hexagons of 1.39 Å sides. The tin–carbon distances for each pair of Sn–C bonds were restrained to within 0.01 Å of each other. The carbonmethylene–carbonphenylene distances were restrained to 1.50±0.01 Å and the carbon–chlorine distances were restrained to 1.75±0.01 Å. The temperature factors of the primed atoms were set to those of the unprimed ones; the anisotropic temperature factors of the disordered carbon atoms were restrained to be nearly isotropic. The disorder refined to a 79:21 ratio.

The final difference Fourier map had a highest peak in the vicinity of C26.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) tris(2-chlorobenzyl)(1,2,4-triazoleyl-5-thiolato)tin at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Thermal ellipsoid plot (Barbour, 2001) tris(2-chlorobenzyl)(1,3,4-triazole-2-thiolato)tin at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn(C7H6Cl)3(C2H2N3S)]Z = 4
Mr = 595.52F(000) = 1184
Triclinic, P1Dx = 1.658 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.696 (6) ÅCell parameters from 9913 reflections
b = 11.385 (5) Åθ = 2.2–28.3°
c = 23.670 (11) ŵ = 1.51 mm1
α = 83.06 (2)°T = 100 K
β = 79.200 (18)°Polycrystals, colorless
γ = 68.559 (18)°0.35 × 0.25 × 0.15 mm
V = 2385 (2) Å3

Data collection

Bruker SMART APEX diffractometer10780 independent reflections
Radiation source: fine-focus sealed tube9232 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scansθmax = 27.5°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.620, Tmax = 0.805k = −14→14
22480 measured reflectionsl = −28→30

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0391P)2 + 3.8486P] where P = (Fo2 + 2Fc2)/3
10780 reflections(Δ/σ)max = 0.001
560 parametersΔρmax = 1.41 e Å3
104 restraintsΔρmin = −0.81 e Å3

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

xyzUiso*/UeqOcc. (<1)
Sn10.64284 (2)0.717035 (18)0.636789 (9)0.01646 (6)
Sn20.82300 (2)0.96070 (2)0.862329 (9)0.02124 (6)
Cl10.62336 (10)0.70680 (8)0.46944 (4)0.03049 (18)
Cl20.33404 (9)0.65825 (8)0.75698 (4)0.03087 (18)
Cl31.04011 (8)0.67040 (7)0.67373 (4)0.02481 (16)
Cl40.5643 (5)0.7542 (3)0.85926 (18)0.0329 (5)0.73 (1)
Cl4'0.5454 (17)0.7760 (9)0.8523 (6)0.0329 (5)0.27
Cl50.89631 (14)0.75253 (11)0.99446 (4)0.0507 (3)
Cl60.7594 (2)1.12134 (15)1.00302 (6)0.0495 (4)0.73 (1)
Cl6'0.8829 (6)1.0551 (4)0.98374 (18)0.0495 (4)0.27
S10.54143 (8)0.95007 (7)0.63370 (3)0.02102 (15)
S20.75356 (9)0.97103 (9)0.76652 (3)0.02605 (17)
N10.8550 (3)0.9981 (2)0.51761 (11)0.0189 (5)
N20.7975 (3)0.9781 (2)0.57403 (11)0.0175 (5)
H20.83990.96920.60390.021*
N30.6304 (3)0.9951 (2)0.51800 (11)0.0185 (5)
N41.0966 (3)0.9713 (3)0.65034 (11)0.0222 (5)
N50.9523 (3)0.9742 (2)0.66902 (11)0.0193 (5)
N61.0439 (3)0.9690 (2)0.74744 (11)0.0191 (5)
H61.05470.96790.78280.023*
C10.8193 (3)0.6591 (3)0.56364 (13)0.0201 (6)
H1A0.80680.72970.53390.024*
H1B0.91800.63840.57600.024*
C20.8145 (3)0.5466 (3)0.53875 (13)0.0193 (6)
C30.7299 (3)0.5566 (3)0.49549 (14)0.0221 (6)
C40.7265 (4)0.4518 (3)0.47200 (15)0.0258 (7)
H40.66980.46240.44190.031*
C50.8065 (4)0.3317 (3)0.49289 (16)0.0285 (7)
H50.80410.25930.47750.034*
C60.8897 (4)0.3182 (3)0.53623 (15)0.0268 (7)
H6A0.94380.23600.55100.032*
C70.8948 (3)0.4238 (3)0.55845 (14)0.0227 (6)
H70.95420.41240.58770.027*
C80.4607 (3)0.6561 (3)0.62835 (15)0.0225 (6)
H8A0.36400.72070.64340.027*
H8B0.46110.64880.58710.027*
C90.4733 (3)0.5316 (3)0.66031 (14)0.0212 (6)
C100.4184 (3)0.5209 (3)0.71877 (15)0.0236 (7)
C110.4267 (4)0.4066 (3)0.74811 (16)0.0287 (7)
H110.38480.40370.78770.034*
C120.4971 (4)0.2957 (3)0.71903 (17)0.0317 (8)
H120.50400.21630.73860.038*
C130.5569 (4)0.3018 (3)0.66141 (17)0.0300 (8)
H130.60710.22630.64150.036*
C140.5437 (3)0.4178 (3)0.63259 (15)0.0246 (7)
H140.58360.42040.59280.029*
C150.7312 (3)0.6453 (3)0.71648 (14)0.0225 (6)
H15A0.76090.70920.73090.027*
H15B0.65320.62740.74600.027*
C160.8643 (3)0.5269 (3)0.70591 (13)0.0212 (6)
C171.0099 (3)0.5266 (3)0.68595 (14)0.0213 (6)
C181.1331 (4)0.4161 (3)0.67527 (15)0.0254 (7)
H181.23050.41940.66220.030*
C191.1113 (4)0.3010 (3)0.68398 (16)0.0307 (8)
H191.19410.22460.67700.037*
C200.9681 (4)0.2977 (3)0.70295 (16)0.0292 (7)
H200.95290.21890.70880.035*
C210.8477 (4)0.4085 (3)0.71337 (14)0.0247 (7)
H210.75050.40440.72600.030*
C220.6639 (3)0.9754 (3)0.57264 (13)0.0160 (5)
C230.7537 (3)1.0078 (3)0.48527 (13)0.0196 (6)
H230.76631.02180.44450.024*
C240.6163 (7)0.955 (2)0.9154 (3)0.023 (2)0.73 (1)
H24A0.63160.86750.93090.028*0.73 (1)
H24B0.59331.00840.94860.028*0.73 (1)
C250.4840 (10)1.0009 (6)0.8834 (5)0.0233 (10)0.73 (1)
C260.4562 (9)0.9136 (4)0.8551 (5)0.0232 (9)0.73 (1)
C270.3408 (7)0.9537 (3)0.8223 (3)0.0251 (10)0.73 (1)
H270.32180.89400.80290.030*0.73 (1)
C280.2531 (5)1.0810 (4)0.8177 (2)0.0253 (11)0.73 (1)
H280.17411.10840.79530.030*0.73 (1)
C290.2808 (6)1.1683 (3)0.8460 (3)0.0342 (13)0.73 (1)
H290.22091.25530.84290.041*0.73 (1)
C300.3963 (9)1.1282 (5)0.8788 (4)0.0297 (11)0.73 (1)
H300.41531.18790.89820.036*0.73 (1)
C24'0.6154 (19)0.969 (6)0.9188 (9)0.023 (2)0.27
H24C0.62500.88470.93750.028*0.27 (1)
H24D0.59461.02860.94930.028*0.27 (1)
C25'0.489 (3)1.0132 (19)0.8843 (15)0.0233 (10)0.27
C26'0.448 (3)0.9380 (11)0.8533 (14)0.0232 (9)0.27
C27'0.325 (2)0.9913 (12)0.8246 (10)0.0251 (10)0.27
H27'0.29720.94000.80340.030*0.27 (1)
C28'0.2423 (17)1.1199 (13)0.8269 (7)0.0253 (11)0.27
H28'0.15801.15630.80730.030*0.27 (1)
C29'0.283 (2)1.1950 (10)0.8579 (8)0.0342 (13)0.27
H29'0.22641.28290.85950.041*0.27 (1)
C30'0.406 (3)1.1417 (18)0.8866 (12)0.0297 (11)0.27
H30'0.43391.19310.90770.036*0.27 (1)
C311.0163 (4)0.7921 (4)0.86879 (17)0.0355 (8)
H31A1.08400.78050.83140.043*
H31B1.07160.80120.89820.043*
C320.9715 (4)0.6791 (3)0.88492 (15)0.0281 (7)
C330.9136 (4)0.6515 (4)0.94113 (16)0.0309 (8)
C340.8664 (5)0.5499 (5)0.9566 (2)0.0546 (14)
H340.82770.53340.99540.066*
C350.8772 (7)0.4727 (5)0.9137 (3)0.075 (2)
H350.84650.40150.92310.090*
C360.9321 (7)0.4986 (4)0.8574 (3)0.0683 (18)
H360.93700.44620.82820.082*
C370.9799 (5)0.5996 (4)0.84321 (19)0.0441 (10)
H371.01930.61530.80430.053*
C380.8610 (11)1.1337 (7)0.8715 (5)0.038 (2)0.73 (1)
H38A0.93821.11470.89670.046*0.73 (1)
H38B0.90071.16400.83320.046*0.73 (1)
C390.7219 (3)1.2377 (3)0.89641 (13)0.0305 (10)0.73 (1)
C400.6696 (4)1.2378 (3)0.95525 (12)0.0314 (11)0.73 (1)
C410.5421 (4)1.3355 (3)0.97739 (11)0.0455 (14)0.73 (1)
H410.50641.33551.01760.055*0.73 (1)
C420.4669 (4)1.4330 (3)0.94069 (16)0.0513 (16)0.73 (1)
H420.37981.49980.95580.062*0.73 (1)
C430.5192 (4)1.4329 (3)0.88185 (15)0.0451 (13)0.73 (1)
H430.46781.49960.85680.054*0.73 (1)
C440.6467 (4)1.3353 (3)0.85971 (10)0.0289 (10)0.73 (1)
H440.68241.33520.81950.035*0.73 (1)
C38'0.863 (3)1.137 (2)0.8598 (17)0.038 (2)0.27
H38C0.96211.12160.87040.046*0.27 (1)
H38D0.85971.17890.82050.046*0.27 (1)
C39'0.7410 (11)1.2202 (10)0.9021 (4)0.0305 (10)0.27
C40'0.7423 (10)1.1869 (8)0.9605 (4)0.0314 (11)0.27
C41'0.6279 (13)1.2578 (10)1.0009 (3)0.0455 (14)0.27
H41'0.62871.23501.04080.055*0.27 (1)
C42'0.5121 (11)1.3620 (10)0.9829 (4)0.0513 (16)0.27
H42'0.43391.41041.01050.062*0.27 (1)
C43'0.5108 (11)1.3953 (9)0.9245 (5)0.0451 (13)0.27
H43'0.43171.46650.91220.054*0.27 (1)
C44'0.6253 (13)1.3244 (10)0.8841 (3)0.0289 (10)0.27
H44'0.62441.34720.84410.035*0.27 (1)
C450.9244 (3)0.9717 (3)0.72669 (13)0.0188 (6)
C461.1446 (3)0.9682 (3)0.69898 (13)0.0203 (6)
H461.24300.96560.70020.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01163 (10)0.01449 (10)0.02346 (11)−0.00542 (8)−0.00056 (7)−0.00253 (7)
Sn20.01800 (11)0.02336 (12)0.02437 (12)−0.00923 (9)−0.00485 (8)−0.00019 (8)
Cl10.0314 (4)0.0200 (4)0.0403 (5)−0.0047 (3)−0.0153 (4)−0.0016 (3)
Cl20.0206 (4)0.0294 (4)0.0421 (5)−0.0091 (3)0.0041 (3)−0.0138 (4)
Cl30.0204 (4)0.0200 (4)0.0366 (4)−0.0100 (3)−0.0051 (3)−0.0006 (3)
Cl40.0486 (15)0.0211 (13)0.0303 (13)−0.0117 (11)−0.0123 (8)0.0018 (9)
Cl4'0.0486 (15)0.0211 (13)0.0303 (13)−0.0117 (11)−0.0123 (8)0.0018 (9)
Cl50.0627 (7)0.0537 (7)0.0326 (5)−0.0101 (5)−0.0222 (5)−0.0013 (4)
Cl60.0773 (10)0.0460 (8)0.0423 (8)−0.0346 (8)−0.0306 (7)0.0080 (6)
Cl6'0.0773 (10)0.0460 (8)0.0423 (8)−0.0346 (8)−0.0306 (7)0.0080 (6)
S10.0170 (3)0.0154 (3)0.0278 (4)−0.0055 (3)0.0039 (3)−0.0023 (3)
S20.0184 (4)0.0399 (5)0.0237 (4)−0.0159 (3)−0.0053 (3)0.0054 (3)
N10.0157 (12)0.0193 (13)0.0227 (13)−0.0082 (10)−0.0029 (10)0.0010 (10)
N20.0150 (12)0.0202 (13)0.0197 (12)−0.0079 (10)−0.0057 (9)0.0004 (10)
N30.0166 (12)0.0160 (12)0.0238 (13)−0.0063 (10)−0.0056 (10)0.0010 (10)
N40.0186 (13)0.0233 (14)0.0240 (13)−0.0076 (11)−0.0018 (10)−0.0005 (11)
N50.0171 (12)0.0220 (13)0.0209 (13)−0.0094 (10)−0.0034 (10)−0.0001 (10)
N60.0180 (12)0.0207 (13)0.0194 (12)−0.0074 (10)−0.0048 (10)0.0006 (10)
C10.0141 (13)0.0236 (15)0.0231 (15)−0.0086 (12)0.0025 (11)−0.0054 (12)
C20.0118 (13)0.0190 (15)0.0262 (15)−0.0056 (11)0.0028 (11)−0.0061 (12)
C30.0164 (14)0.0185 (15)0.0287 (16)−0.0036 (12)−0.0018 (12)−0.0019 (12)
C40.0245 (16)0.0232 (16)0.0321 (18)−0.0094 (14)−0.0043 (13)−0.0077 (13)
C50.0268 (17)0.0204 (16)0.0389 (19)−0.0113 (14)0.0041 (14)−0.0091 (14)
C60.0177 (15)0.0185 (15)0.0381 (19)−0.0026 (12)0.0038 (13)−0.0030 (13)
C70.0149 (14)0.0228 (16)0.0273 (16)−0.0048 (12)0.0023 (12)−0.0040 (13)
C80.0128 (14)0.0195 (15)0.0379 (18)−0.0084 (12)−0.0041 (12)−0.0025 (13)
C90.0109 (13)0.0173 (14)0.0369 (18)−0.0060 (11)−0.0030 (12)−0.0050 (13)
C100.0122 (13)0.0195 (15)0.0388 (18)−0.0051 (12)−0.0004 (12)−0.0076 (13)
C110.0223 (16)0.0274 (17)0.0395 (19)−0.0135 (14)−0.0051 (14)0.0022 (15)
C120.0230 (17)0.0204 (16)0.054 (2)−0.0091 (14)−0.0120 (15)0.0055 (15)
C130.0160 (15)0.0170 (15)0.057 (2)−0.0032 (13)−0.0052 (15)−0.0094 (15)
C140.0130 (14)0.0226 (16)0.0385 (18)−0.0064 (12)−0.0019 (12)−0.0057 (14)
C150.0186 (15)0.0229 (16)0.0248 (16)−0.0067 (13)−0.0005 (12)−0.0032 (12)
C160.0201 (15)0.0225 (16)0.0221 (15)−0.0089 (13)−0.0053 (12)0.0023 (12)
C170.0192 (15)0.0175 (15)0.0281 (16)−0.0069 (12)−0.0058 (12)0.0002 (12)
C180.0148 (14)0.0231 (16)0.0362 (18)−0.0040 (13)−0.0070 (13)0.0020 (13)
C190.0225 (17)0.0190 (16)0.044 (2)0.0007 (13)−0.0085 (14)0.0031 (14)
C200.0308 (18)0.0195 (16)0.0377 (19)−0.0102 (14)−0.0086 (15)0.0068 (14)
C210.0203 (15)0.0245 (16)0.0304 (17)−0.0104 (13)−0.0053 (13)0.0048 (13)
C220.0122 (13)0.0126 (13)0.0227 (14)−0.0038 (11)−0.0020 (11)−0.0017 (11)
C230.0179 (14)0.0171 (14)0.0226 (15)−0.0051 (12)−0.0035 (11)0.0011 (11)
C240.0267 (16)0.028 (5)0.0201 (18)−0.0167 (16)−0.0017 (13)−0.005 (2)
C250.0197 (16)0.034 (2)0.0220 (16)−0.0179 (17)0.0001 (12)−0.0017 (18)
C260.0288 (19)0.021 (2)0.0219 (17)−0.014 (2)−0.0002 (14)0.001 (3)
C270.029 (2)0.028 (3)0.0266 (19)−0.019 (3)−0.0029 (17)−0.007 (3)
C280.0201 (18)0.028 (3)0.031 (3)−0.010 (2)−0.0047 (17)−0.010 (2)
C290.0265 (19)0.028 (3)0.051 (4)−0.011 (2)−0.005 (2)−0.012 (2)
C300.019 (2)0.037 (2)0.039 (3)−0.0146 (18)−0.0045 (17)−0.008 (2)
C24'0.0267 (16)0.028 (5)0.0201 (18)−0.0167 (16)−0.0017 (13)−0.005 (2)
C25'0.0197 (16)0.034 (2)0.0220 (16)−0.0179 (17)0.0001 (12)−0.0017 (18)
C26'0.0288 (19)0.021 (2)0.0219 (17)−0.014 (2)−0.0002 (14)0.001 (3)
C27'0.029 (2)0.028 (3)0.0266 (19)−0.019 (3)−0.0029 (17)−0.007 (3)
C28'0.0201 (18)0.028 (3)0.031 (3)−0.010 (2)−0.0047 (17)−0.010 (2)
C29'0.0265 (19)0.028 (3)0.051 (4)−0.011 (2)−0.005 (2)−0.012 (2)
C30'0.019 (2)0.037 (2)0.039 (3)−0.0146 (18)−0.0045 (17)−0.008 (2)
C310.0222 (17)0.034 (2)0.043 (2)−0.0055 (15)−0.0066 (15)0.0122 (16)
C320.0248 (17)0.0248 (17)0.0314 (18)−0.0021 (14)−0.0132 (14)0.0036 (14)
C330.0321 (19)0.0328 (19)0.0324 (18)−0.0138 (16)−0.0168 (15)0.0074 (15)
C340.052 (3)0.062 (3)0.066 (3)−0.039 (2)−0.038 (2)0.039 (2)
C350.085 (4)0.037 (3)0.135 (6)−0.038 (3)−0.087 (4)0.033 (3)
C360.087 (4)0.031 (2)0.099 (4)−0.005 (2)−0.074 (4)−0.005 (3)
C370.044 (2)0.034 (2)0.044 (2)0.0098 (18)−0.0240 (19)−0.0100 (17)
C380.038 (2)0.039 (2)0.045 (5)−0.0258 (19)0.009 (3)−0.015 (2)
C390.034 (2)0.034 (2)0.033 (2)−0.0213 (19)−0.0053 (17)−0.0086 (17)
C400.039 (3)0.030 (3)0.033 (2)−0.019 (2)−0.006 (2)−0.009 (2)
C410.058 (4)0.040 (3)0.043 (3)−0.026 (3)0.008 (2)−0.017 (2)
C420.054 (4)0.046 (3)0.058 (4)−0.021 (3)−0.001 (3)−0.021 (3)
C430.052 (3)0.039 (3)0.057 (3)−0.023 (3)−0.024 (3)−0.001 (2)
C440.048 (3)0.036 (2)0.013 (2)−0.028 (2)−0.006 (2)0.003 (2)
C38'0.038 (2)0.039 (2)0.045 (5)−0.0258 (19)0.009 (3)−0.015 (2)
C39'0.034 (2)0.034 (2)0.033 (2)−0.0213 (19)−0.0053 (17)−0.0086 (17)
C40'0.039 (3)0.030 (3)0.033 (2)−0.019 (2)−0.006 (2)−0.009 (2)
C41'0.058 (4)0.040 (3)0.043 (3)−0.026 (3)0.008 (2)−0.017 (2)
C42'0.054 (4)0.046 (3)0.058 (4)−0.021 (3)−0.001 (3)−0.021 (3)
C43'0.052 (3)0.039 (3)0.057 (3)−0.023 (3)−0.024 (3)−0.001 (2)
C44'0.048 (3)0.036 (2)0.013 (2)−0.028 (2)−0.006 (2)0.003 (2)
C450.0167 (14)0.0158 (14)0.0241 (15)−0.0062 (11)−0.0045 (11)0.0020 (11)
C460.0145 (14)0.0185 (15)0.0254 (16)−0.0037 (12)−0.0019 (11)−0.0012 (12)

Geometric parameters (Å, °)

Sn1—C152.163 (3)C20—H200.9500
Sn1—C12.168 (3)C21—H210.9500
Sn1—C82.168 (3)C23—H230.9500
Sn1—S12.4667 (14)C24—C251.508 (5)
Sn2—C312.151 (4)C24—H24A0.9900
Sn2—C382.174 (5)C24—H24B0.9900
Sn2—C38'2.174 (8)C25—C261.3900
Sn2—C24'2.174 (8)C25—C301.3900
Sn2—C242.174 (4)C26—C271.3900
Sn2—S22.4617 (13)C27—C281.3900
Cl1—C31.751 (3)C27—H270.9500
Cl2—C101.749 (3)C28—C291.3900
Cl3—C171.748 (3)C28—H280.9500
Cl4—C261.734 (3)C29—C301.3900
Cl4'—C26'1.738 (9)C29—H290.9500
Cl5—C331.754 (4)C30—H300.9500
Cl6—C401.720 (3)C24'—C25'1.501 (10)
Cl6'—C40'1.732 (7)C24'—H24C0.9900
Cl6'—Cl6'i2.379 (9)C24'—H24D0.9900
S1—C221.757 (3)C25'—C26'1.3900
S2—C451.748 (3)C25'—C30'1.3900
N1—C231.321 (4)C26'—C27'1.3900
N1—N21.374 (3)C27'—C28'1.3900
N2—C221.314 (4)C27'—H27'0.9500
N2—H20.8600C28'—C29'1.3900
N3—C231.343 (4)C28'—H28'0.9500
N3—C221.365 (4)C29'—C30'1.3900
N4—C461.312 (4)C29'—H29'0.9500
N4—N51.376 (4)C30'—H30'0.9500
N5—C451.340 (4)C31—C321.489 (5)
N6—C451.329 (4)C31—H31A0.9900
N6—C461.359 (4)C31—H31B0.9900
N6—H60.8600C32—C371.391 (5)
C1—C21.493 (4)C32—C331.390 (5)
C1—H1A0.9900C33—C341.379 (5)
C1—H1B0.9900C34—C351.387 (8)
C2—C31.397 (4)C34—H340.9500
C2—C71.400 (4)C35—C361.378 (9)
C3—C41.389 (4)C35—H350.9500
C4—C51.386 (5)C36—C371.374 (7)
C4—H40.9500C36—H360.9500
C5—C61.381 (5)C37—H370.9500
C5—H50.9500C38—C391.507 (7)
C6—C71.389 (5)C38—H38A0.9900
C6—H6A0.9500C38—H38B0.9900
C7—H70.9500C39—C401.3900
C8—C91.499 (4)C39—C441.3900
C8—H8A0.9900C40—C411.3900
C8—H8B0.9900C41—C421.3900
C9—C101.394 (5)C41—H410.9500
C9—C141.402 (4)C42—C431.3900
C10—C111.382 (5)C42—H420.9500
C11—C121.392 (5)C43—C441.3900
C11—H110.9500C43—H430.9500
C12—C131.383 (5)C44—H440.9500
C12—H120.9500C38'—C39'1.501 (10)
C13—C141.385 (5)C38'—H38C0.9900
C13—H130.9500C38'—H38D0.9900
C14—H140.9500C39'—C40'1.3900
C15—C161.495 (4)C39'—C44'1.3900
C15—H15A0.9900C40'—C41'1.3900
C15—H15B0.9900C41'—C42'1.3900
C16—C211.401 (4)C41'—H41'0.9500
C16—C171.401 (4)C42'—C43'1.3900
C17—C181.393 (5)C42'—H42'0.9500
C18—C191.388 (5)C43'—C44'1.3900
C18—H180.9500C43'—H43'0.9500
C19—C201.390 (5)C44'—H44'0.9500
C19—H190.9500C46—H460.9500
C20—C211.381 (5)
C15—Sn1—C1110.37 (12)C26—C25—C24118.5 (9)
C15—Sn1—C8112.66 (12)C30—C25—C24121.3 (9)
C1—Sn1—C8109.34 (13)C27—C26—C25120.0
C15—Sn1—S1109.39 (9)C27—C26—Cl4118.7 (4)
C1—Sn1—S1108.10 (9)C25—C26—Cl4121.3 (4)
C8—Sn1—S1106.83 (9)C26—C27—C28120.0
C31—Sn2—C38113.9 (3)C26—C27—H27120.0
C31—Sn2—C38'115.4 (10)C28—C27—H27120.0
C38—Sn2—C38'7.2 (14)C27—C28—C29120.0
C31—Sn2—C24'117.7 (15)C27—C28—H28120.0
C38—Sn2—C24'106.8 (19)C29—C28—H28120.0
C38'—Sn2—C24'110.8 (19)C30—C29—C28120.0
C31—Sn2—C24115.2 (5)C30—C29—H29120.0
C38—Sn2—C24111.5 (6)C28—C29—H29120.0
C38'—Sn2—C24115.5 (7)C29—C30—C25120.0
C24'—Sn2—C245(2)C29—C30—H30120.0
C31—Sn2—S2107.24 (12)C25—C30—H30120.0
C38—Sn2—S2108.5 (4)C25'—C24'—Sn2109.5 (18)
C38'—Sn2—S2101.5 (13)C25'—C24'—H24C109.8
C24'—Sn2—S2101.8 (7)Sn2—C24'—H24C109.8
C24—Sn2—S299.2 (2)C25'—C24'—H24D109.8
C40'—Cl6'—Cl6'i155.1 (5)Sn2—C24'—H24D109.8
C22—S1—Sn197.09 (10)H24C—C24'—H24D108.2
C45—S2—Sn296.57 (11)C26'—C25'—C30'120.0
C23—N1—N2108.2 (2)C26'—C25'—C24'126 (3)
C22—N2—N1105.2 (2)C30'—C25'—C24'114 (3)
C22—N2—H2127.4C25'—C26'—C27'120.0
N1—N2—H2127.4C25'—C26'—Cl4'120.7 (14)
C23—N3—C22103.9 (2)C27'—C26'—Cl4'119.3 (14)
C46—N4—N5102.1 (2)C26'—C27'—C28'120.0
C45—N5—N4109.5 (2)C26'—C27'—H27'120.0
C45—N6—C46102.8 (3)C28'—C27'—H27'120.0
C45—N6—H6128.6C29'—C28'—C27'120.0
C46—N6—H6128.6C29'—C28'—H28'120.0
C2—C1—Sn1110.57 (19)C27'—C28'—H28'120.0
C2—C1—H1A109.5C28'—C29'—C30'120.0
Sn1—C1—H1A109.5C28'—C29'—H29'120.0
C2—C1—H1B109.5C30'—C29'—H29'120.0
Sn1—C1—H1B109.5C29'—C30'—C25'120.0
H1A—C1—H1B108.1C29'—C30'—H30'120.0
C3—C2—C7116.3 (3)C25'—C30'—H30'120.0
C3—C2—C1122.7 (3)C32—C31—Sn2111.0 (2)
C7—C2—C1121.0 (3)C32—C31—H31A109.4
C4—C3—C2122.7 (3)Sn2—C31—H31A109.4
C4—C3—Cl1118.2 (3)C32—C31—H31B109.4
C2—C3—Cl1119.1 (2)Sn2—C31—H31B109.4
C5—C4—C3119.4 (3)H31A—C31—H31B108.0
C5—C4—H4120.3C37—C32—C33117.1 (4)
C3—C4—H4120.3C37—C32—C31120.7 (4)
C6—C5—C4119.5 (3)C33—C32—C31122.1 (3)
C6—C5—H5120.3C34—C33—C32123.0 (4)
C4—C5—H5120.3C34—C33—Cl5118.6 (3)
C5—C6—C7120.5 (3)C32—C33—Cl5118.3 (3)
C5—C6—H6A119.8C33—C34—C35118.0 (5)
C7—C6—H6A119.8C33—C34—H34121.0
C6—C7—C2121.6 (3)C35—C34—H34121.0
C6—C7—H7119.2C36—C35—C34120.4 (4)
C2—C7—H7119.2C36—C35—H35119.8
C9—C8—Sn1112.0 (2)C34—C35—H35119.8
C9—C8—H8A109.2C35—C36—C37120.5 (5)
Sn1—C8—H8A109.2C35—C36—H36119.7
C9—C8—H8B109.2C37—C36—H36119.7
Sn1—C8—H8B109.2C36—C37—C32120.9 (5)
H8A—C8—H8B107.9C36—C37—H37119.5
C10—C9—C14116.0 (3)C32—C37—H37119.5
C10—C9—C8122.8 (3)C39—C38—Sn2113.5 (4)
C14—C9—C8121.2 (3)C39—C38—H38A108.9
C11—C10—C9123.0 (3)Sn2—C38—H38A108.9
C11—C10—Cl2118.2 (3)C39—C38—H38B108.9
C9—C10—Cl2118.8 (2)Sn2—C38—H38B108.9
C10—C11—C12119.2 (3)H38A—C38—H38B107.7
C10—C11—H11120.4C40—C39—C44120.0
C12—C11—H11120.4C40—C39—C38121.0 (5)
C13—C12—C11119.5 (3)C44—C39—C38119.0 (5)
C13—C12—H12120.2C39—C40—C41120.0
C11—C12—H12120.2C39—C40—Cl6122.2 (2)
C12—C13—C14120.1 (3)C41—C40—Cl6117.8 (2)
C12—C13—H13119.9C42—C41—C40120.0
C14—C13—H13119.9C42—C41—H41120.0
C13—C14—C9122.0 (3)C40—C41—H41120.0
C13—C14—H14119.0C41—C42—C43120.0
C9—C14—H14119.0C41—C42—H42120.0
C16—C15—Sn1109.2 (2)C43—C42—H42120.0
C16—C15—H15A109.8C44—C43—C42120.0
Sn1—C15—H15A109.8C44—C43—H43120.0
C16—C15—H15B109.8C42—C43—H43120.0
Sn1—C15—H15B109.8C43—C44—C39120.0
H15A—C15—H15B108.3C43—C44—H44120.0
C21—C16—C17116.1 (3)C39—C44—H44120.0
C21—C16—C15120.7 (3)C39'—C38'—Sn2107.3 (8)
C17—C16—C15123.1 (3)C39'—C38'—H38C110.3
C18—C17—C16122.8 (3)Sn2—C38'—H38C110.3
C18—C17—Cl3118.0 (2)C39'—C38'—H38D110.3
C16—C17—Cl3119.2 (2)Sn2—C38'—H38D110.3
C19—C18—C17118.9 (3)H38C—C38'—H38D108.5
C19—C18—H18120.5C40'—C39'—C44'120.0
C17—C18—H18120.5C40'—C39'—C38'118 (2)
C18—C19—C20119.8 (3)C44'—C39'—C38'122 (2)
C18—C19—H19120.1C39'—C40'—C41'120.0
C20—C19—H19120.1C39'—C40'—Cl6'120.7 (7)
C21—C20—C19120.2 (3)C41'—C40'—Cl6'119.2 (7)
C21—C20—H20119.9C42'—C41'—C40'120.0
C19—C20—H20119.9C42'—C41'—H41'120.0
C20—C21—C16122.1 (3)C40'—C41'—H41'120.0
C20—C21—H21118.9C41'—C42'—C43'120.0
C16—C21—H21118.9C41'—C42'—H42'120.0
N2—C22—N3112.1 (2)C43'—C42'—H42'120.0
N2—C22—S1124.3 (2)C44'—C43'—C42'120.0
N3—C22—S1123.6 (2)C44'—C43'—H43'120.0
N1—C23—N3110.5 (3)C42'—C43'—H43'120.0
N1—C23—H23124.7C43'—C44'—C39'120.0
N3—C23—H23124.7C43'—C44'—H44'120.0
C25—C24—Sn2113.4 (6)C39'—C44'—H44'120.0
C25—C24—H24A108.9N6—C45—N5110.1 (3)
Sn2—C24—H24A108.9N6—C45—S2126.8 (2)
C25—C24—H24B108.9N5—C45—S2123.1 (2)
Sn2—C24—H24B108.9N4—C46—N6115.4 (3)
H24A—C24—H24B107.7N4—C46—H46122.3
C26—C25—C30120.0N6—C46—H46122.3
C15—Sn1—S1—C22117.76 (13)C24—C25—C30—C29176.0 (10)
C1—Sn1—S1—C22−2.45 (13)C31—Sn2—C24'—C25'−132 (3)
C8—Sn1—S1—C22−120.02 (14)C38—Sn2—C24'—C25'99 (4)
C31—Sn2—S2—C45−58.74 (15)C38'—Sn2—C24'—C25'92 (4)
C38—Sn2—S2—C4564.7 (2)C24—Sn2—C24'—C25'−72 (9)
C38'—Sn2—S2—C4562.7 (6)S2—Sn2—C24'—C25'−15 (4)
C24'—Sn2—S2—C45177.1 (19)Sn2—C24'—C25'—C26'84 (4)
C24—Sn2—S2—C45−178.8 (6)Sn2—C24'—C25'—C30'−97 (3)
C23—N1—N2—C220.7 (3)C30'—C25'—C26'—C27'0.0
C46—N4—N5—C45−0.5 (3)C24'—C25'—C26'—C27'178 (3)
C15—Sn1—C1—C298.9 (2)C30'—C25'—C26'—Cl4'−177 (2)
C8—Sn1—C1—C2−25.5 (2)C24'—C25'—C26'—Cl4'1(2)
S1—Sn1—C1—C2−141.5 (2)C25'—C26'—C27'—C28'0.0
Sn1—C1—C2—C389.6 (3)Cl4'—C26'—C27'—C28'177 (2)
Sn1—C1—C2—C7−89.7 (3)C26'—C27'—C28'—C29'0.0
C7—C2—C3—C4−1.2 (5)C27'—C28'—C29'—C30'0.0
C1—C2—C3—C4179.5 (3)C28'—C29'—C30'—C25'0.0
C7—C2—C3—Cl1178.8 (2)C26'—C25'—C30'—C29'0.0
C1—C2—C3—Cl1−0.5 (4)C24'—C25'—C30'—C29'−178 (3)
C2—C3—C4—C51.8 (5)C38—Sn2—C31—C32158.0 (4)
Cl1—C3—C4—C5−178.2 (3)C38'—Sn2—C31—C32165.8 (11)
C3—C4—C5—C6−0.8 (5)C24'—Sn2—C31—C3231.9 (15)
C4—C5—C6—C7−0.7 (5)C24—Sn2—C31—C3227.3 (5)
C5—C6—C7—C21.2 (5)S2—Sn2—C31—C32−82.0 (3)
C3—C2—C7—C6−0.2 (4)Sn2—C31—C32—C3799.2 (4)
C1—C2—C7—C6179.1 (3)Sn2—C31—C32—C33−77.8 (4)
C15—Sn1—C8—C9−28.2 (3)C37—C32—C33—C340.5 (6)
C1—Sn1—C8—C994.9 (2)C31—C32—C33—C34177.6 (4)
S1—Sn1—C8—C9−148.4 (2)C37—C32—C33—Cl5−178.2 (3)
Sn1—C8—C9—C1085.0 (3)C31—C32—C33—Cl5−1.1 (5)
Sn1—C8—C9—C14−94.2 (3)C32—C33—C34—C35−0.3 (6)
C14—C9—C10—C11−2.3 (5)Cl5—C33—C34—C35178.4 (3)
C8—C9—C10—C11178.4 (3)C33—C34—C35—C36−0.6 (7)
C14—C9—C10—Cl2178.1 (2)C34—C35—C36—C371.4 (8)
C8—C9—C10—Cl2−1.1 (4)C35—C36—C37—C32−1.2 (7)
C9—C10—C11—C122.2 (5)C33—C32—C37—C360.3 (6)
Cl2—C10—C11—C12−178.2 (2)C31—C32—C37—C36−176.9 (4)
C10—C11—C12—C13−0.3 (5)C31—Sn2—C38—C39−150.9 (7)
C11—C12—C13—C14−1.4 (5)C38'—Sn2—C38—C39106 (9)
C12—C13—C14—C91.3 (5)C24'—Sn2—C38—C39−19.3 (10)
C10—C9—C14—C130.6 (4)C24—Sn2—C38—C39−18.4 (9)
C8—C9—C14—C13179.8 (3)S2—Sn2—C38—C3989.8 (7)
C1—Sn1—C15—C16−27.4 (2)Sn2—C38—C39—C4078.8 (8)
C8—Sn1—C15—C1695.2 (2)Sn2—C38—C39—C44−102.0 (6)
S1—Sn1—C15—C16−146.19 (18)C44—C39—C40—C410.0
Sn1—C15—C16—C21−91.4 (3)C38—C39—C40—C41179.2 (5)
Sn1—C15—C16—C1785.8 (3)C44—C39—C40—Cl6−178.9 (3)
C21—C16—C17—C18−1.6 (5)C38—C39—C40—Cl60.3 (5)
C15—C16—C17—C18−178.9 (3)C39—C40—C41—C420.0
C21—C16—C17—Cl3178.5 (2)Cl6—C40—C41—C42178.9 (3)
C15—C16—C17—Cl31.1 (4)C40—C41—C42—C430.0
C16—C17—C18—C190.8 (5)C41—C42—C43—C440.0
Cl3—C17—C18—C19−179.2 (3)C42—C43—C44—C390.0
C17—C18—C19—C200.1 (5)C40—C39—C44—C430.0
C18—C19—C20—C21−0.3 (5)C38—C39—C44—C43−179.2 (5)
C19—C20—C21—C16−0.5 (5)C31—Sn2—C38'—C39'−132 (2)
C17—C16—C21—C201.4 (5)C38—Sn2—C38'—C39'−52 (6)
C15—C16—C21—C20178.8 (3)C24'—Sn2—C38'—C39'5(3)
N1—N2—C22—N3−1.1 (3)C24—Sn2—C38'—C39'6(3)
N1—N2—C22—S1179.1 (2)S2—Sn2—C38'—C39'112 (2)
C23—N3—C22—N21.1 (3)Sn2—C38'—C39'—C40'70 (2)
C23—N3—C22—S1−179.1 (2)Sn2—C38'—C39'—C44'−107.1 (18)
Sn1—S1—C22—N2−85.9 (3)C44'—C39'—C40'—C41'0.0
Sn1—S1—C22—N394.3 (2)C38'—C39'—C40'—C41'−177.1 (13)
N2—N1—C23—N30.0 (3)C44'—C39'—C40'—Cl6'178.4 (9)
C22—N3—C23—N1−0.7 (3)C38'—C39'—C40'—Cl6'1.3 (12)
C31—Sn2—C24—C25−132.8 (10)Cl6'i—Cl6'—C40'—C39'92.8 (12)
C38—Sn2—C24—C2595.4 (12)Cl6'i—Cl6'—C40'—C41'−88.8 (13)
C38'—Sn2—C24—C2588.8 (19)C39'—C40'—C41'—C42'0.0
C24'—Sn2—C24—C25105 (13)Cl6'—C40'—C41'—C42'−178.4 (9)
S2—Sn2—C24—C25−18.7 (13)C40'—C41'—C42'—C43'0.0
Sn2—C24—C25—C2689.1 (12)C41'—C42'—C43'—C44'0.0
Sn2—C24—C25—C30−87.0 (12)C42'—C43'—C44'—C39'0.0
C30—C25—C26—C270.0C40'—C39'—C44'—C43'0.0
C24—C25—C26—C27−176.1 (10)C38'—C39'—C44'—C43'177.0 (13)
C30—C25—C26—Cl4179.5 (8)C46—N6—C45—N5−0.8 (3)
C24—C25—C26—Cl43.3 (7)C46—N6—C45—S2178.7 (2)
C25—C26—C27—C280.0N4—N5—C45—N60.9 (3)
Cl4—C26—C27—C28−179.5 (8)N4—N5—C45—S2−178.7 (2)
C26—C27—C28—C290.0Sn2—S2—C45—N6−0.8 (3)
C27—C28—C29—C300.0Sn2—S2—C45—N5178.7 (2)
C28—C29—C30—C250.0N5—N4—C46—N60.0 (3)
C26—C25—C30—C290.0C45—N6—C46—N40.5 (4)

Symmetry codes: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···N50.862.072.916 (4)170

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5006).

References

  • Aziz-ur-Rehman, Ali, S., Shahzadi, S. & Helliwell, M. (2006). Acta Cryst. E62, m2328–m2329.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ma, C.-L., Li, J.-K., Zhang, R.-F. & Qiu, L.-L. (2007). J. Mol. Struct.830, 1–7.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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