supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

gk2113 scheme

Acta Cryst. (2008). E64, o278    [ doi:10.1107/S1600536807066329 ]

C60 1,1,2,2-tetrachloroethylene tetrasolvate

C. Arunkumar, P. Bhyrappa and B. Varghese

Abstract top

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 [pi]-[pi] in nature.

Comment top

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]

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altormare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997.

Figures top
[Figure 1] 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).
[Figure 2] Fig. 2. View of the crystal packing in the title compound along the b axis.
(I) top
Crystal data top
C60·4C2Cl4Z = 1
Mr = 1383.88F000 = 680
Triclinic, P1Dx = 1.916 Mg m−3
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 mm−1
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 top
Bruker APEX2 Kappa
diffractometer		4047 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 φ 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 top
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 Å−3
4047 reflectionsΔρmin = −0.68 e Å−3
420 parametersExtinction correction: none
34 restraints
Crystal data top
C60·4C2Cl4γ = 79.834 (5)º
Mr = 1383.88V = 1199.6 (10) Å3
Triclinic, P1Z = 1
a = 10.049 (5) ÅMo Kα
b = 10.168 (5) ŵ = 0.97 mm−1
c = 13.412 (5) ÅT = 173 (2) K
α = 70.484 (5)º0.3 × 0.2 × 0.2 mm
β = 68.508 (5)º
Data collection top
Bruker APEX2 Kappa
diffractometer		4047 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		3502 reflections with I > 2σ(I)
Tmin = 0.759, Tmax = 0.830Rint = 0.037
11755 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.10534 restraints
wR(F2) = 0.265  w = 1/[σ2(Fo2) + (0.0602P)2 + 20.5574P]
where P = (Fo2 + 2Fc2)/3
S = 1.11Δρmax = 1.25 e Å−3
4047 reflectionsΔρmin = −0.68 e Å−3
420 parameters
Special details top

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) top
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) top
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, °) top
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.
Acknowledgements top

This work was suported 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.

references
References top

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.

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.

Soldatov, D. V., Diamente, P. R., Ratcliffe, C. I. & Ripmeester, J. A. (2001). Inorg. Chem. 40, 5660–5667.