PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o278.
Published online 2007 December 18. doi:  10.1107/S1600536807066329
PMCID: PMC2915331

C60 1,1,2,2-tetra­chloro­ethyl­ene tetra­solvate

Abstract

In the title complex, C60·4C2Cl4, the C60 mol­ecule is located on an inversion centre and there are two tetra­chloro­ethyl­ene (TCE) mol­ecules in the asymmetric unit. Both TCE mol­ecules show positional disorder, with occupancy ratios of 0.75:0.25 and 0.56:0.44. Four fullerene C atoms form short contacts [3.208 (17) and 3.223 (17) Å] with the centres of the TCE double bonds, indicating that C60–solvent inter­actions are largely π–π in nature.

Related literature

For related literature on inclusion compounds of C60 with various guest mol­ecules, see: Balch & Olmstead (1999 [triangle]) and references cited therein; Olmstead et al. (2000 [triangle]); Hardie et al. (2003 [triangle]); Bond (2003 [triangle]); Litvinov et al. (2003 [triangle]); Soldatov et al. (2001 [triangle]); Dodrick et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o278-scheme1.jpg

Experimental

Crystal data

  • C60·4C2Cl4
  • M r = 1383.88
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o278-efi1.jpg
  • a = 10.049 (5) Å
  • b = 10.168 (5) Å
  • c = 13.412 (5) Å
  • α = 70.484 (5)°
  • β = 68.508 (5)°
  • γ = 79.834 (5)°
  • V = 1199.6 (10) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.97 mm−1
  • T = 173 (2) K
  • 0.3 × 0.2 × 0.2 mm

Data collection

  • Bruker Kappa APEX2 diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.759, T max = 0.830
  • 11755 measured reflections
  • 4047 independent reflections
  • 3502 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.105
  • wR(F 2) = 0.265
  • S = 1.11
  • 4047 reflections
  • 420 parameters
  • 34 restraints
  • Δρmax = 1.25 e Å−3
  • Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altormare et al., 1993 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks 1, I. DOI: 10.1107/S1600536807066329/gk2113sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066329/gk2113Isup2.hkl

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

Acknowledgments

This work was supported by funds from the Defence Research Development Organization, Government of India, to PB. We thank Mr V. Ramkumar for assistance with the data collection and the Department of Chemistry, IIT Madras, Chennai, for the XRD facility.

supplementary crystallographic information

Comment

C60 is located around inversion centre and there are two symmetry independent 1,1,2,2-tetrachloroethylene (TCE) solvent molecules in the asymmetric unit. The ORTEP drawing of the title compound is shown in Fig. 1. In the C60 molecule inter-pentagonal bond distances are in the range 1.3947 (17)–1.414 (15) Å while the intra-pentagonal bond distances are in the range 1.364 (19)–1.55 (2) Å. Such a variation in bond lengths is possibly due to the librational motion of the C60 molecule in the crystal. Similar variations of bond lengths were observed in some other C60 co-crystals (Dodrick et al., 2005). The C60 and TCE molecules show intermolecular π-π interactions (Fig. 2). The short contacts between the fullerene C2 atom and the centre of the ethylene C33A—C34A bond, and C22 atom and the centre of the ethylene C31A—C32A bond are of 3.208 (17) and 3.223 (17) Å, respectively. Additionally, short contacts are observed between Cl atoms of TCE and C60 (Cl7···C14i 3.419 (14) Å, Cl5···Cl4 = 3.491 (4) Å; symmetry code: (i) x, -1 + y, z]. The solvent molecules and C60 are located in alternating layers parallel to the (001) plane. The shortest C60···C60 contacts are: C27···C29i 3.690 (14) Å and C9···C11ii 3.447 (14) Å [symmetry code: (i) 2 - x, 1 - y, -z, (ii) 1 - x, -y, -z]

Experimental

C60 sample was purchased from Sigma-Aldrich and used as received. The solvents for crystallization, 1,1,2,2-tetrachloroethylene (TCE) and methanol were of purity >99% and were purchased from E. Merck (Germany). Crystals of the C60. 4(CCl4) were grown by diffusion of methanol into a solution of C60 in TCE over a period of five days. Upon removal from the mother liquor the crystals were unstable anad therefore were mounted at 0°C.

Refinement

The C60 molecule was refined without any restraints. Both TCE molecules were disordered and showed two approximately perpendicular orientations with overlapping Cl atoms (the ratio of occupancies 0.75:0.25 and 0.56:0.44). Since one of the disordered TCE molecules showed occupancies very close to 0.75 and 0.25 these values were fixed at the final stages of the refinement. The restraints were imposed on C—C and C—Cl bond lengths of the TCE molecules and anisotropic displacement parameters of C31A, C32A and C34A atoms. The residual peak of 1.25 e Å-3 is located at 1.06 Å from the C5 atom of C60 indicating that in addition to large librational motion the C60 molecule can be also partially disordered. The high residual values, R1=0.105 and wR1=0.259 are most probably due to disorder of the TCE and C60 molecules.

Figures

Fig. 1.
ORTEP diagram of the title compound showing 50% probability displacement ellipsoids. Labels for C60 were omitted. The TCE molecules in minor occupancies are not shown. Symmetry code for the atoms not from the asymmetric unit(_2): 2 - x, -y, -z).
Fig. 2.
View of the crystal packing in the title compound along the b axis.

Crystal data

C60·4C2Cl4Z = 1
Mr = 1383.88F000 = 680
Triclinic, P1Dx = 1.916 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.049 (5) ÅCell parameters from 9670 reflections
b = 10.168 (5) Åθ = 2.2–28.4º
c = 13.412 (5) ŵ = 0.97 mm1
α = 70.484 (5)ºT = 173 (2) K
β = 68.508 (5)ºPlate, brown
γ = 79.834 (5)º0.3 × 0.2 × 0.2 mm
V = 1199.6 (10) Å3

Data collection

Bruker APEX2 Kappa diffractometer4047 independent reflections
Radiation source: fine-focus sealed tube3502 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 173(2) Kθmax = 25.0º
ω and [var phi] scanθmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 1999)h = −11→11
Tmin = 0.759, Tmax = 0.830k = −12→11
11755 measured reflectionsl = −15→15

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)] = 0.105  w = 1/[σ2(Fo2) + (0.0602P)2 + 20.5574P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.265(Δ/σ)max < 0.001
S = 1.11Δρmax = 1.25 e Å3
4047 reflectionsΔρmin = −0.68 e Å3
420 parametersExtinction correction: none
34 restraints

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)
C10.7872 (12)0.2020 (11)0.1752 (10)0.048 (3)
C20.8649 (12)0.1051 (13)0.2458 (9)0.050 (3)
C30.8346 (14)−0.0347 (13)0.2881 (8)0.053 (3)
C40.7301 (14)−0.0837 (17)0.2621 (11)0.069 (4)
C50.6574 (12)−0.0048 (16)0.2046 (11)0.069 (4)
C60.6836 (10)0.1484 (11)0.1574 (9)0.044 (3)
C70.6674 (10)0.1949 (11)0.0509 (10)0.043 (2)
C80.6353 (9)0.0806 (11)0.0226 (9)0.038 (2)
C90.6293 (9)−0.0449 (12)0.1128 (11)0.051 (3)
C100.6808 (12)−0.1691 (13)0.0941 (14)0.068 (4)
C110.6954 (10)0.0755 (11)−0.0878 (9)0.043 (3)
C121.2500 (12)0.0616 (14)0.1058 (11)0.055 (3)
C131.2598 (12)0.1767 (11)0.0131 (12)0.051 (3)
C140.7609 (12)−0.2663 (12)0.1663 (12)0.062 (4)
C150.7816 (13)−0.2274 (11)0.2465 (9)0.052 (3)
C160.9231 (17)−0.2585 (12)0.2626 (9)0.063 (4)
C170.9541 (18)−0.1434 (13)0.2871 (8)0.064 (4)
C181.0919 (15)−0.1027 (16)0.2459 (9)0.064 (4)
C191.1206 (14)0.0448 (15)0.2018 (10)0.057 (3)
C201.0097 (15)0.1432 (14)0.2030 (10)0.059 (3)
C211.2117 (14)−0.1785 (12)0.1725 (11)0.060 (3)
C221.1800 (13)−0.2823 (11)0.1474 (10)0.052 (3)
C231.0266 (11)−0.3278 (10)0.1968 (9)0.043 (2)
C240.7594 (10)0.2949 (10)−0.0361 (9)0.041 (2)
C251.0019 (12)−0.3678 (9)0.1130 (10)0.045 (3)
C260.8641 (12)0.3473 (10)−0.0120 (12)0.053 (3)
C270.8788 (13)0.3009 (11)0.0902 (10)0.049 (3)
C281.0212 (15)0.2708 (13)0.1026 (12)0.061 (3)
C291.1246 (13)0.3373 (10)−0.0941 (10)0.049 (3)
C301.1358 (17)0.2883 (12)0.0146 (12)0.065 (4)
C311.3841 (11)0.4523 (10)0.2363 (7)0.027 (3)0.82 (2)
C321.3342 (11)0.4954 (11)0.3232 (7)0.029 (3)0.82 (2)
C31A1.306 (2)0.430 (3)0.3017 (15)0.013 (10)0.18 (2)
C32A1.406 (2)0.515 (3)0.2605 (15)0.007 (9)0.18 (2)
C330.7666 (10)0.1574 (11)0.4919 (11)0.030 (5)0.56 (3)
C340.6841 (11)0.2472 (11)0.4454 (12)0.039 (5)0.56 (3)
C33A0.7762 (13)0.2488 (14)0.4439 (16)0.039 (7)0.44 (3)
C34A0.677 (2)0.162 (2)0.4950 (19)0.034 (6)0.44 (3)
Cl11.5322 (2)0.5188 (2)0.12839 (19)0.0357 (6)
Cl21.2994 (3)0.3299 (3)0.2202 (2)0.0484 (7)
Cl31.4140 (3)0.6192 (3)0.3386 (2)0.0425 (6)
Cl41.1832 (3)0.4285 (3)0.4339 (2)0.0566 (8)
Cl50.9370 (3)0.2011 (4)0.4666 (2)0.0569 (8)
Cl60.7062 (3)−0.0017 (3)0.5858 (2)0.0535 (7)
Cl70.7431 (4)0.4076 (3)0.3547 (2)0.0615 (9)
Cl80.5146 (3)0.2052 (3)0.4689 (2)0.0565 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C20.053 (7)0.072 (8)0.036 (6)0.006 (6)−0.008 (5)−0.043 (6)
C30.073 (8)0.064 (8)0.012 (4)−0.005 (6)0.002 (5)−0.016 (5)
C60.026 (5)0.042 (6)0.042 (6)0.015 (4)0.011 (4)−0.021 (5)
C70.023 (5)0.039 (6)0.065 (7)0.019 (4)−0.015 (5)−0.023 (5)
C80.014 (4)0.046 (6)0.058 (6)0.003 (4)−0.017 (4)−0.018 (5)
C90.007 (4)0.054 (7)0.077 (8)−0.007 (4)−0.004 (5)−0.009 (6)
C100.026 (6)0.055 (8)0.114 (12)−0.025 (5)−0.015 (7)−0.011 (8)
C120.040 (6)0.088 (9)0.069 (8)−0.008 (6)−0.035 (6)−0.041 (7)
C130.039 (6)0.040 (6)0.090 (9)−0.015 (5)−0.037 (6)−0.018 (6)
C140.038 (6)0.043 (6)0.079 (9)−0.033 (5)−0.015 (6)0.024 (6)
C150.053 (7)0.031 (5)0.035 (6)−0.016 (5)0.019 (5)0.006 (4)
C170.121 (12)0.055 (7)0.017 (5)−0.007 (7)−0.032 (6)0.001 (5)
C190.067 (8)0.082 (9)0.054 (7)0.002 (7)−0.044 (7)−0.036 (7)
C200.089 (10)0.066 (8)0.052 (7)0.003 (7)−0.042 (7)−0.039 (6)
C210.072 (8)0.040 (6)0.076 (9)0.003 (6)−0.055 (7)0.003 (6)
C220.063 (7)0.041 (6)0.051 (7)0.027 (5)−0.045 (6)0.000 (5)
C230.048 (6)0.026 (5)0.042 (6)−0.001 (4)−0.020 (5)0.010 (4)
C240.032 (5)0.024 (5)0.063 (7)0.015 (4)−0.019 (5)−0.011 (4)
C250.053 (6)0.009 (4)0.061 (7)−0.007 (4)−0.015 (5)0.004 (4)
C260.050 (6)0.017 (5)0.090 (9)0.011 (4)−0.019 (6)−0.025 (5)
C270.060 (7)0.035 (6)0.063 (7)0.009 (5)−0.019 (6)−0.037 (5)
C280.080 (9)0.053 (7)0.080 (9)−0.008 (6)−0.031 (8)−0.048 (7)
C290.065 (8)0.019 (5)0.065 (7)−0.014 (5)−0.031 (6)0.003 (5)
C300.096 (10)0.040 (6)0.079 (9)−0.036 (7)−0.034 (8)−0.020 (6)
C310.028 (6)0.023 (5)0.028 (6)−0.005 (4)−0.009 (5)−0.001 (4)
C320.028 (6)0.034 (6)0.027 (6)0.002 (5)−0.014 (5)−0.010 (5)
C31A0.014 (11)0.013 (11)0.014 (11)0.000 (5)−0.004 (6)−0.005 (6)
C32A0.008 (10)0.007 (10)0.006 (11)0.000 (5)−0.001 (6)−0.003 (5)
C330.023 (10)0.039 (11)0.024 (9)0.009 (9)−0.004 (8)−0.012 (8)
C340.051 (13)0.024 (10)0.025 (10)−0.008 (9)0.008 (9)−0.006 (8)
C33A0.042 (15)0.046 (15)0.030 (13)−0.012 (13)−0.006 (12)−0.015 (11)
C34A0.019 (11)0.028 (12)0.037 (13)−0.007 (10)0.010 (10)−0.007 (10)
Cl10.0277 (11)0.0402 (13)0.0334 (12)−0.0031 (9)−0.0002 (9)−0.0140 (10)
Cl20.0645 (17)0.0344 (13)0.0625 (17)−0.0119 (12)−0.0345 (14)−0.0150 (12)
Cl30.0450 (14)0.0485 (14)0.0442 (14)−0.0097 (11)−0.0119 (11)−0.0262 (11)
Cl40.0426 (15)0.074 (2)0.0378 (14)−0.0217 (14)0.0055 (11)−0.0085 (13)
Cl50.0457 (16)0.086 (2)0.0461 (16)−0.0226 (15)−0.0169 (13)−0.0166 (15)
Cl60.0653 (18)0.0400 (14)0.0425 (15)−0.0036 (12)−0.0213 (13)0.0076 (11)
Cl70.104 (3)0.0280 (13)0.0343 (14)−0.0175 (14)−0.0051 (15)0.0002 (10)
Cl80.0380 (14)0.0658 (18)0.0538 (17)0.0013 (13)−0.0180 (12)−0.0021 (14)
C160.111 (11)0.041 (6)0.022 (5)−0.027 (7)−0.020 (6)0.017 (5)
C50.028 (6)0.092 (10)0.047 (7)−0.001 (6)0.020 (5)−0.007 (7)
C10.046 (6)0.043 (6)0.061 (7)0.017 (5)−0.009 (5)−0.041 (6)
C110.028 (5)0.052 (6)0.054 (6)−0.004 (4)−0.033 (5)−0.001 (5)
C180.078 (9)0.100 (11)0.028 (6)0.001 (8)−0.043 (6)−0.010 (6)
C40.044 (7)0.100 (11)0.040 (7)−0.015 (7)0.016 (6)−0.019 (7)

Geometric parameters (Å, °)

C2—C31.386 (17)C23—C251.426 (16)
C2—C201.426 (17)C24—C22i1.432 (16)
C2—C11.457 (16)C24—C261.433 (16)
C3—C41.429 (19)C25—C29i1.350 (16)
C3—C171.482 (19)C25—C26i1.505 (16)
C6—C11.382 (16)C26—C271.348 (17)
C6—C71.408 (15)C26—C25i1.505 (16)
C6—C51.504 (18)C27—C11.396 (16)
C7—C241.414 (15)C27—C281.468 (17)
C7—C81.454 (14)C28—C301.299 (19)
C8—C111.394 (15)C29—C25i1.350 (16)
C8—C91.427 (15)C29—C301.415 (17)
C9—C101.347 (17)C29—C14i1.463 (19)
C9—C51.55 (2)C31—C321.280 (2)
C10—C13i1.364 (19)C31—Cl11.699 (10)
C10—C141.487 (18)C31—Cl21.735 (10)
C12—C131.379 (18)C32—Cl31.709 (10)
C12—C191.443 (17)C32—Cl41.735 (10)
C12—C11i1.471 (16)C31A—C32A1.282 (2)
C13—C10i1.364 (19)C31A—Cl21.747 (9)
C13—C301.529 (19)C31A—Cl41.748 (9)
C14—C151.354 (19)C32A—Cl31.751 (9)
C14—C29i1.463 (19)C32A—Cl11.751 (9)
C15—C161.480 (19)C33—C341.281 (2)
C15—C41.517 (19)C33—Cl51.728 (8)
C17—C181.372 (19)C33—Cl61.731 (8)
C17—C161.427 (17)C34—Cl81.720 (8)
C19—C201.360 (18)C34—Cl71.726 (8)
C19—C181.454 (19)C33A—C34A1.281 (2)
C20—C281.510 (19)C33A—Cl51.711 (9)
C21—C221.327 (17)C33A—Cl71.721 (9)
C21—C11i1.426 (16)C34A—Cl81.75 (2)
C21—C181.524 (19)C34A—Cl61.75 (2)
C22—C24i1.432 (16)C5—C41.251 (19)
C22—C231.525 (16)C11—C21i1.426 (16)
C23—C161.358 (17)C11—C12i1.471 (16)
C3—C2—C20120.2 (11)C27—C26—C24121.6 (11)
C3—C2—C1119.0 (11)C27—C26—C25i117.9 (11)
C20—C2—C1108.6 (11)C24—C26—C25i108.2 (10)
C2—C3—C4120.7 (12)C26—C27—C1118.9 (11)
C2—C3—C17119.2 (12)C26—C27—C28121.0 (11)
C4—C3—C17107.2 (11)C1—C27—C28108.6 (11)
C1—C6—C7119.7 (10)C30—C28—C27120.3 (13)
C1—C6—C5121.1 (11)C30—C28—C20121.0 (13)
C7—C6—C5107.4 (11)C27—C28—C20106.3 (11)
C6—C7—C24118.8 (10)C25i—C29—C30123.2 (12)
C6—C7—C8111.1 (9)C25i—C29—C14i117.5 (11)
C24—C7—C8117.6 (10)C30—C29—C14i108.4 (11)
C11—C8—C9119.7 (10)C28—C30—C29120.3 (14)
C11—C8—C7118.9 (9)C28—C30—C13119.0 (12)
C9—C8—C7109.3 (10)C29—C30—C13107.8 (12)
C10—C9—C8121.5 (12)C32—C31—Cl1121.3 (8)
C10—C9—C5120.3 (12)C32—C31—Cl2121.7 (8)
C8—C9—C5106.4 (10)Cl1—C31—Cl2117.0 (5)
C9—C10—C13i119.8 (13)C31—C32—Cl3122.2 (9)
C9—C10—C14117.8 (14)C31—C32—Cl4121.7 (9)
C13i—C10—C14110.6 (12)Cl3—C32—Cl4116.0 (5)
C13—C12—C19119.7 (12)C32A—C31A—Cl2117.9 (7)
C13—C12—C11i118.3 (11)C32A—C31A—Cl4116.8 (7)
C19—C12—C11i109.1 (11)Cl2—C31A—Cl4125.3 (7)
C10i—C13—C12123.0 (12)C31A—C32A—Cl3119.1 (7)
C10i—C13—C30107.0 (11)C31A—C32A—Cl1118.2 (7)
C12—C13—C30119.8 (12)Cl3—C32A—Cl1122.7 (6)
C15—C14—C29i121.7 (11)C34—C33—Cl5119.1 (7)
C15—C14—C10119.8 (13)C34—C33—Cl6121.0 (7)
C29i—C14—C10106.2 (12)Cl5—C33—Cl6119.8 (5)
C14—C15—C16119.4 (11)C33—C34—Cl8119.7 (7)
C14—C15—C4121.6 (12)C33—C34—Cl7120.9 (7)
C16—C15—C4105.7 (11)Cl8—C34—Cl7119.3 (5)
C18—C17—C16119.9 (14)C34A—C33A—Cl5118.4 (14)
C18—C17—C3119.0 (12)C34A—C33A—Cl7119.0 (14)
C16—C17—C3109.9 (13)Cl5—C33A—Cl7122.6 (7)
C20—C19—C12120.6 (13)C33A—C34A—Cl8119.4 (17)
C20—C19—C18119.7 (12)C33A—C34A—Cl6120.8 (17)
C12—C19—C18108.0 (11)Cl8—C34A—Cl6119.8 (7)
C19—C20—C2121.4 (12)C23—C16—C17121.5 (13)
C19—C20—C28119.8 (13)C23—C16—C15117.9 (11)
C2—C20—C28106.7 (11)C17—C16—C15108.4 (12)
C22—C21—C11i120.2 (13)C4—C5—C6118.8 (15)
C22—C21—C18119.0 (12)C4—C5—C9122.0 (14)
C11i—C21—C18107.1 (11)C6—C5—C9105.8 (11)
C21—C22—C24i121.0 (12)C6—C1—C27122.1 (11)
C21—C22—C23119.6 (11)C6—C1—C2117.2 (10)
C24i—C22—C23108.4 (10)C27—C1—C2109.7 (10)
C16—C23—C25121.6 (11)C8—C11—C21i121.5 (11)
C16—C23—C22119.6 (11)C8—C11—C12i117.6 (10)
C25—C23—C22106.5 (9)C21i—C11—C12i108.6 (11)
C7—C24—C22i120.8 (10)C17—C18—C19120.6 (13)
C7—C24—C26118.8 (10)C17—C18—C21120.2 (13)
C22i—C24—C26108.7 (10)C19—C18—C21107.1 (11)
C29i—C25—C23121.9 (11)C5—C4—C3123.1 (15)
C29i—C25—C26i117.2 (11)C5—C4—C15118.2 (15)
C23—C25—C26i108.2 (9)C3—C4—C15108.9 (12)
C20—C2—C3—C4−137.2 (11)Cl5—C33—C34—Cl8179.6 (9)
C1—C2—C3—C40.8 (15)Cl6—C33—C34—Cl8−4(2)
C20—C2—C3—C17−0.7 (14)Cl5—C33—C34—Cl72(2)
C1—C2—C3—C17137.3 (10)Cl6—C33—C34—Cl7178.3 (10)
C1—C6—C7—C240.7 (13)Cl5—C33A—C34A—Cl8−177.4 (12)
C5—C6—C7—C24−142.6 (9)Cl7—C33A—C34A—Cl82(3)
C1—C6—C7—C8141.9 (9)Cl5—C33A—C34A—Cl60(3)
C5—C6—C7—C8−1.4 (10)Cl7—C33A—C34A—Cl6179.4 (12)
C6—C7—C8—C11−142.2 (9)C32—C31—Cl1—C32A0(2)
C24—C7—C8—C11−0.4 (13)Cl2—C31—Cl1—C32A177 (3)
C6—C7—C8—C90.3 (10)C31A—C32A—Cl1—C310(2)
C24—C7—C8—C9142.0 (9)Cl3—C32A—Cl1—C31179 (4)
C11—C8—C9—C100.1 (14)C32—C31—Cl2—C31A−2(3)
C7—C8—C9—C10−141.9 (10)Cl1—C31—Cl2—C31A−179 (3)
C11—C8—C9—C5143.0 (9)C32A—C31A—Cl2—C312(2)
C7—C8—C9—C51.0 (10)Cl4—C31A—Cl2—C31180 (5)
C8—C9—C10—C13i0.0 (15)C31—C32—Cl3—C32A1(3)
C5—C9—C10—C13i−137.9 (11)Cl4—C32—Cl3—C32A180 (3)
C8—C9—C10—C14139.6 (11)C31A—C32A—Cl3—C32−1(2)
C5—C9—C10—C141.7 (15)Cl1—C32A—Cl3—C32−180 (4)
C19—C12—C13—C10i−138.2 (11)C31—C32—Cl4—C31A0(2)
C11i—C12—C13—C10i−0.8 (15)Cl3—C32—Cl4—C31A−179 (3)
C19—C12—C13—C302.4 (15)C32A—C31A—Cl4—C320(2)
C11i—C12—C13—C30139.8 (10)Cl2—C31A—Cl4—C32−178 (5)
C9—C10—C14—C15−1.0 (15)C34A—C33A—Cl5—C332.6 (16)
C13i—C10—C14—C15142.1 (11)Cl7—C33A—Cl5—C33−177 (3)
C9—C10—C14—C29i−143.9 (10)C34—C33—Cl5—C33A0.4 (18)
C13i—C10—C14—C29i−0.8 (12)Cl6—C33—Cl5—C33A−176 (2)
C29i—C14—C15—C16−0.6 (15)C34—C33—Cl6—C34A−0.7 (18)
C10—C14—C15—C16−137.7 (11)Cl5—C33—Cl6—C34A175 (3)
C29i—C14—C15—C4134.6 (11)C33A—C34A—Cl6—C33−2.6 (17)
C10—C14—C15—C4−2.5 (16)Cl8—C34A—Cl6—C33174 (3)
C2—C3—C17—C181.1 (15)C34A—C33A—Cl7—C34−1.0 (17)
C4—C3—C17—C18142.8 (10)Cl5—C33A—Cl7—C34179 (3)
C2—C3—C17—C16−142.6 (10)C33—C34—Cl7—C33A−2.1 (18)
C4—C3—C17—C16−0.9 (12)Cl8—C34—Cl7—C33A−179 (3)
C13—C12—C19—C20−1.9 (15)C33—C34—Cl8—C34A3.8 (17)
C11i—C12—C19—C20−142.7 (10)Cl7—C34—Cl8—C34A−179 (3)
C13—C12—C19—C18141.0 (10)C33A—C34A—Cl8—C34−0.7 (18)
C11i—C12—C19—C180.2 (11)Cl6—C34A—Cl8—C34−178 (3)
C12—C19—C20—C2138.1 (11)C25—C23—C16—C17−137.0 (11)
C18—C19—C20—C2−0.6 (16)C22—C23—C16—C170.0 (15)
C12—C19—C20—C280.6 (15)C25—C23—C16—C151.1 (14)
C18—C19—C20—C28−138.1 (11)C22—C23—C16—C15138.1 (10)
C3—C2—C20—C190.5 (15)C18—C17—C16—C23−1.6 (16)
C1—C2—C20—C19−141.3 (10)C3—C17—C16—C23141.8 (11)
C3—C2—C20—C28142.7 (10)C18—C17—C16—C15−143.1 (11)
C1—C2—C20—C280.9 (11)C3—C17—C16—C150.2 (12)
C11i—C21—C22—C24i1.4 (16)C14—C15—C16—C23−1.2 (14)
C18—C21—C22—C24i136.9 (11)C4—C15—C16—C23−142.6 (10)
C11i—C21—C22—C23−138.4 (11)C14—C15—C16—C17142.0 (10)
C18—C21—C22—C23−2.8 (15)C4—C15—C16—C170.5 (11)
C21—C22—C23—C162.3 (14)C1—C6—C5—C41.0 (16)
C24i—C22—C23—C16−142.0 (10)C7—C6—C5—C4143.6 (11)
C21—C22—C23—C25145.0 (10)C1—C6—C5—C9−140.7 (10)
C24i—C22—C23—C250.7 (10)C7—C6—C5—C91.9 (10)
C6—C7—C24—C22i137.9 (10)C10—C9—C5—C41.5 (17)
C8—C7—C24—C22i−0.8 (13)C8—C9—C5—C4−141.9 (12)
C6—C7—C24—C26−1.1 (13)C10—C9—C5—C6141.7 (10)
C8—C7—C24—C26−139.9 (9)C8—C9—C5—C6−1.8 (10)
C16—C23—C25—C29i0.8 (15)C7—C6—C1—C27−0.6 (14)
C22—C23—C25—C29i−141.0 (9)C5—C6—C1—C27137.6 (10)
C16—C23—C25—C26i141.4 (10)C7—C6—C1—C2−141.0 (9)
C22—C23—C25—C26i−0.4 (10)C5—C6—C1—C2−2.8 (14)
C7—C24—C26—C271.6 (14)C26—C27—C1—C61.1 (15)
C22i—C24—C26—C27−141.9 (10)C28—C27—C1—C6−142.7 (9)
C7—C24—C26—C25i143.1 (9)C26—C27—C1—C2144.0 (10)
C22i—C24—C26—C25i−0.4 (11)C28—C27—C1—C20.2 (11)
C24—C26—C27—C1−1.6 (15)C3—C2—C1—C61.9 (14)
C25i—C26—C27—C1−139.5 (10)C20—C2—C1—C6144.2 (9)
C24—C26—C27—C28137.6 (11)C3—C2—C1—C27−143.1 (9)
C25i—C26—C27—C28−0.3 (14)C20—C2—C1—C27−0.7 (11)
C26—C27—C28—C30−0.1 (16)C9—C8—C11—C21i−137.7 (10)
C1—C27—C28—C30142.9 (11)C7—C8—C11—C21i0.8 (14)
C26—C27—C28—C20−142.6 (10)C9—C8—C11—C12i0.2 (12)
C1—C27—C28—C200.3 (11)C7—C8—C11—C12i138.7 (9)
C19—C20—C28—C300.0 (16)C16—C17—C18—C19138.8 (11)
C2—C20—C28—C30−142.9 (11)C3—C17—C18—C19−1.2 (15)
C19—C20—C28—C27142.2 (10)C16—C17—C18—C211.0 (16)
C2—C20—C28—C27−0.8 (11)C3—C17—C18—C21−139.1 (11)
C27—C28—C30—C290.3 (16)C20—C19—C18—C171.0 (16)
C20—C28—C30—C29137.3 (12)C12—C19—C18—C17−142.3 (10)
C27—C28—C30—C13−136.5 (11)C20—C19—C18—C21143.7 (10)
C20—C28—C30—C130.6 (16)C12—C19—C18—C210.4 (11)
C25i—C29—C30—C28−0.2 (17)C22—C21—C18—C171.3 (16)
C14i—C29—C30—C28−143.2 (11)C11i—C21—C18—C17142.0 (11)
C25i—C29—C30—C13140.8 (10)C22—C21—C18—C19−141.5 (10)
C14i—C29—C30—C13−2.2 (11)C11i—C21—C18—C19−0.8 (11)
C10i—C13—C30—C28144.3 (11)C6—C5—C4—C31.9 (18)
C12—C13—C30—C28−1.8 (15)C9—C5—C4—C3137.2 (13)
C10i—C13—C30—C292.7 (11)C6—C5—C4—C15−140.2 (11)
C12—C13—C30—C29−143.5 (10)C9—C5—C4—C15−4.9 (17)
Cl1—C31—C32—Cl3−1.3 (14)C2—C3—C4—C5−2.8 (18)
Cl2—C31—C32—Cl3−178.3 (6)C17—C3—C4—C5−143.9 (12)
Cl1—C31—C32—Cl4180.0 (6)C2—C3—C4—C15142.2 (10)
Cl2—C31—C32—Cl43.0 (14)C17—C3—C4—C151.2 (12)
Cl2—C31A—C32A—Cl3178.6 (19)C14—C15—C4—C55.5 (16)
Cl4—C31A—C32A—Cl31(4)C16—C15—C4—C5145.9 (11)
Cl2—C31A—C32A—Cl1−2(4)C14—C15—C4—C3−141.5 (11)
Cl4—C31A—C32A—Cl1179.8 (19)C16—C15—C4—C3−1.1 (12)

Symmetry codes: (i) −x+2, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2113).

References

  • Altomare, A., Gascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst.26, 343–350.
  • Balch, A. L. & Olmstead, M. M. (1999). Coord. Chem. Rev.185–186, 601–617.
  • Bond, A. D. (2003). Acta Cryst. E59, o1992–o1993.
  • Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 (Version 1.22) and SAINT-Plus (Version 7.6), Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dodrick, M. S., Panthofer, M. & Jansen, M. (2005). Eur. J. Inorg. Chem. pp. 4064–4069.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Hardie, M. J., Torrensa, R. & Raston, C. L. (2003). Chem. Commun. pp. 1854–1855. [PubMed]
  • Litvinov, A. L., Konarev, D. V., Kovalevsky, A. Y., Coppens, P. & Lyubovskaya, R. N. (2003). CrystEngComm, 5, 137–139.
  • Olmstead, M. M., Jiang, F. & Balch, A. L. (2000). Chem. Commun. pp. 483–484.
  • Sheldrick, G. M. (1997). SHELXL97 University of Göttingen, Germany. [PubMed]
  • Soldatov, D. V., Diamente, P. R., Ratcliffe, C. I. & Ripmeester, J. A. (2001). Inorg. Chem.40, 5660–5667. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography