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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o688.
Published online 2008 March 12. doi:  10.1107/S1600536808006235
PMCID: PMC2961057

2-exo,5-endo,8,8,10-Penta­chloro­bornane

Abstract

The title compound, C10H13Cl5, is a polychlorinated monoterpene and a Toxaphene congener. This compound is also the only penta­chlorinated derivative of camphene formed via ionic chlorination. Previously, the title compound was thought to be 2-exo,5-endo,9,9,10-penta­chloro­bornane, but X-ray structural analysis showed it to have a different structure and rather to be 2-exo,5-endo,8,8,10-penta­chloro­bornane. The title compound shows static disorder and almost half the molecule was divided in two partitions with an occupancy ratio of 0.575 (major) to 0.425 (minor). The repulsive close contacts of Cl atoms could possibly be the cause for this disorder.

Related literature

For the preparation of 6-exo-chloro­camphene and further the title compound, see: Jennings & Herschbach (1965 [triangle]). For the background and related compounds, see: Nikiforov et al. (1999 [triangle], 2000 [triangle], 2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o688-scheme1.jpg

Experimental

Crystal data

  • C10H13Cl5
  • M r = 310.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o688-efi1.jpg
  • a = 12.2386 (2) Å
  • b = 9.07010 (10) Å
  • c = 23.0822 (3) Å
  • V = 2562.25 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.10 mm−1
  • T = 173 (2) K
  • 0.24 × 0.16 × 0.10 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (MULABS in PLATON; Blessing, 1995 [triangle]; Spek, 2003 [triangle]) T min = 0.779, T max = 0.898
  • 35431 measured reflections
  • 2612 independent reflections
  • 2440 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.091
  • wR(F 2) = 0.191
  • S = 1.25
  • 2612 reflections
  • 185 parameters
  • 167 restraints
  • H-atom parameters constrained
  • Δρmax = 0.88 e Å−3
  • Δρmin = −0.80 e Å−3

Data collection: COLLECT (Bruker, 2004 [triangle]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]) and DIRAX (Duisenberg,1992 [triangle]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2002 (Burla et al., 2003 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 [triangle]) and Mercury (Macrae et al., 2006 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006235/zl2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006235/zl2100Isup2.hkl

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

Acknowledgments

The work in St. Petersburg University was made possible in part by financial support from the European Commission (Project MODELKEY, Contract No 511237-GOCE).

supplementary crystallographic information

Comment

The title compound (Fig 1) of this study is a polychlorinated monoterpene and a Toxaphene congener. It is prepared via ionic chlorination of 6-exo-chlorocamphene in solution in carbon tetrachloride, followed by chlorination of intermediate dichlorocamphene in presence of Lewis acid (Fig 2). The last transformation obviously involves a series of carbocationic rearrangements, but details of the exact mechanism remain unknown. Based on analytical and mechanistic data the compound was previously proposed to be 2-exo,5-endo,9,9,10-pentachlorobornane (Nikiforov et al., 2001; Nikiforov et al., 2000; Nikiforov et al., 1999), but this was not verified by crystallographic data and so we decided to perform a detailed single-crystal difffraction analysis to unambiguously identify the nature of the pentachlorinated compound. The structure obtained, however, was found to be different from the previously suggested one. The dichloromethyl and methyl groups at carbon atom C7 exhibit a different orientation than previously presumed for 2-exo,5-endo,9,9,10-pentachlorobornane, and the correct name of the title compound should thus be 2-exo,5-endo,8,8,10-pentachlorobornane.

There are only few weak intermolecular C—H···Cl and Cl···Cl contacts found in the structure. The static disorder of the present structure may be a consequence of intermolecular repulsive interactions between chlorines, found between two major components, but no unarguable evidence of this was found from the close contacts. However, the major component presented in Fig 1 has a close Cl···Cl contact of 3.49 Å between Cl2 and Cl5 of its enantiomer at -x, 2 - y, 1 - z. The same contanct is found also between Cl2 of the enantiomer and Cl5 in Fig 1, but between the minor components the contact (Cl2···Cl5b) is a bit longer (3.60 Å). The second difference found in the close contacts between major and minor components was another similar double interaction of major components between Cl5 and H10A at -x, 1 - y, 1 - z. This weak contact (2.59 Å) was not found between the minor components, in which the distance Cl5b···H10c is 3.60 Å.

Experimental

The title compound was prepared via the following steps presented in Fig 2. First 6-exo-chlorocamphene was prepared according to a literature method (Jennings & Herschbach, 1965). Then crude 6-exo-chlorocamphene (5 g, 29 mmol) was dissolved in 50 ml of carbon tetrachloride. Chlorine gas was passed through this solution with stirring. After the solution obtained showed a persistent green colour, SnCl4 (1 g, 4 mmol) was added to the reaction mixture and passing of chlorine and stirring was continued for 4 h. The reaction mixture was washed with water and dried over calcium chloride. The solvent was removed in vacuo and the residue crystallized twice from hexane. The yield of the title compound was 2.2 g (25%, mp. 112 °C). 1H NMR (500 MHz, in CDCl3): 5.98 (H8), 4.43 (H5), 4.37 (H2), 3.89 (H10a), 3.81 (H10b), 3.02 (H3a), 2.63 (H6a), 2.55 (H4), 2.27 (H3b), 1.91 (H6b), 1.62 (3H, H9). 13C NMR (126 MHz, in CDCl3): 76.3 (C8), 63.1 (C2), 61.9 (C1), 56.7 (C7), 55.0 (C5), 54.5 (C4), 44.4 (2 C, C6 & C10), 33.6 (C3), 12.2 (C9). The obtained crystals were suitable for single-crystal X-ray structure determination.

Refinement

The title compound shows static disorder and it was necessary to divide almost half the molecule in two partitions (Fig 3) as well as to use a large number of restraints (see below). The low data quality seems to be, however, not directly linked to the disorder. Refinement with or without the disorder taken into account (the latter with unacceptably asymmetric thermal ellipsoids) did result in nearly the same refined R values. We thus decided to test for various types of twinning, but the crystals did not appear to be twinned. DIRAX (Duisenberg, 1992) found the correct cell with less than one hundred fitting reflections. With relaxed conditions more than three hundred reflections were fitting the lattice. The same cell was also found using reflections that did not fit the first unit cell found using the strict values, but these lattices were rotated with respect to the first by less than 2 ° and attempts to refine the structure as non-merohedrally twinned using the hklf 5 routine failed. Visually the crystals seem to be of good quality with no evident fragmentation, but some fragmentation can be seen when cutting the large crystals The multiple unit cells found have thus been attributed to fragmentation of the single-crystal rather than non merohedral twinning. Several data collection endeavours with different crystals resulted in very similar results.

Very large and asymmetric thermal ellipsoids for several atoms indicated static disorder and atoms Cl1, Cl5, C1, C2, C3 and C10 and hydrogen atoms bonded to C2, C3, C4, C6 and C10 were refined as disordered over two partially occupied positions (Fig 3), with an occupancy ratio of 0.575 (major) to 0.425 (minor). The interatomic distances of non-hydrogen atoms of both partitions were restrained to be similar (SADI restraints with default standard deviations). The ADPs of atoms C1, C2, C3, C4, C6, C10, Cl1 and Cl2 (major) and the corresponding atoms of the minor component were restrained to be similar to those of their neighbors (SIMU and DELU restraints with default standard deviations). The ADPs of the disordered atoms were also restrained to be close to isotropic (ISOR restraints with s equal to 0.01 for C1, C2, C3, C10 (major), C1b, C2b, C3b and C10b (minor) and equal to 0.1 for Cl1, Cl5, Cl1b and Cl5b). The anisotropic displacement parameters of C1 and C1b set to be identical.

All H atoms were visible in electron density maps, but were placed in idealized positions and allowed to ride on their parent atoms at C—H distances of 0.98 (methyl), 0.99 (methylene) and 1.00 Å (methine), with Uiso(H) of 1.5 (methyl) and 1.2 times Ueq(C).

Figures

Fig. 1.
View of the molecule of title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size. The disorder was removed from the figure, showing only the major ...
Fig. 2.
The preparation of title compound.
Fig. 3.
Wireframe view of the title compound, showing the major and minor components.

Crystal data

C10H13Cl5Dx = 1.610 Mg m3
Mr = 310.45Melting point: 385 K
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 61337 reflections
a = 12.2386 (2) Åθ = 0.4–28.3º
b = 9.07010 (10) ŵ = 1.10 mm1
c = 23.0822 (3) ÅT = 173 (2) K
V = 2562.25 (6) Å3Block, colourless
Z = 80.24 × 0.16 × 0.10 mm
F000 = 1264

Data collection

Bruker Kappa APEXII diffractometer2612 independent reflections
Radiation source: fine-focus sealed tube2440 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.064
Detector resolution: 9 pixels mm-1θmax = 26.4º
T = 173(2) Kθmin = 2.4º
[var phi] and ω scansh = −15→15
Absorption correction: multi-scan(MULABS in PLATON; Blessing, 1995; Spek, 2003)k = −10→11
Tmin = 0.779, Tmax = 0.898l = −28→27
35431 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.091H-atom parameters constrained
wR(F2) = 0.191  w = 1/[σ2(Fo2) + 27.3151P] where P = (Fo2 + 2Fc2)/3
S = 1.26(Δ/σ)max < 0.001
2612 reflectionsΔρmax = 0.88 e Å3
185 parametersΔρmin = −0.80 e Å3
167 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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)
C10.0424 (15)0.7026 (18)0.5949 (9)0.0283 (17)0.58 (5)
C20.1274 (12)0.8287 (19)0.5994 (11)0.033 (3)0.58 (5)
H20.13670.87860.56110.040*0.58 (5)
C30.0694 (11)0.933 (2)0.6431 (10)0.036 (4)0.58 (5)
H3A0.11360.94260.67890.043*0.58 (5)
H3B0.06051.03240.62590.043*0.58 (5)
C100.0790 (16)0.5631 (17)0.5651 (9)0.030 (4)0.58 (5)
H10A0.01420.50230.55580.036*0.58 (5)
H10B0.12580.50580.59190.036*0.58 (5)
Cl10.2573 (10)0.7613 (16)0.6257 (11)0.073 (4)0.58 (5)
Cl50.1540 (13)0.6004 (11)0.4994 (7)0.064 (3)0.58 (5)
C1B0.046 (2)0.722 (3)0.5991 (12)0.0283 (17)0.42 (5)
C2B0.1255 (15)0.848 (3)0.6172 (13)0.032 (4)0.42 (5)
H2B0.14010.90600.58120.038*0.42 (5)
C3B0.0629 (16)0.951 (3)0.6584 (13)0.036 (5)0.42 (5)
H3B10.09600.95530.69760.044*0.42 (5)
H3B20.05521.05220.64260.044*0.42 (5)
C10B0.103 (2)0.580 (3)0.5818 (12)0.033 (5)0.42 (5)
H10C0.04920.50000.57700.040*0.42 (5)
H10D0.15610.55090.61220.040*0.42 (5)
Cl1B0.2570 (13)0.795 (3)0.6450 (13)0.072 (5)0.42 (5)
Cl5B0.174 (2)0.613 (2)0.5141 (13)0.082 (6)0.42 (5)
Cl2−0.12193 (14)1.06930 (17)0.57587 (8)0.0370 (4)
Cl3−0.08571 (17)0.4090 (2)0.65640 (9)0.0484 (5)
Cl4−0.20761 (15)0.6378 (3)0.71306 (9)0.0519 (6)
C4−0.0439 (6)0.8662 (7)0.6575 (3)0.0340 (14)
H4B−0.08990.89150.69200.041*0.42 (5)
H4A−0.07970.90430.69350.041*0.58 (5)
C5−0.1096 (5)0.8816 (6)0.6013 (3)0.0261 (13)
H5−0.18420.83900.60710.031*
C6−0.0450 (5)0.7843 (7)0.5581 (3)0.0308 (13)
H6C−0.01360.84340.52610.037*0.42 (5)
H6D−0.09110.70460.54190.037*0.42 (5)
H6A−0.00980.84590.52810.037*0.58 (5)
H6B−0.09440.71300.53890.037*0.58 (5)
C7−0.0150 (5)0.6992 (7)0.6571 (3)0.0264 (13)
C8−0.1180 (5)0.6021 (7)0.6551 (3)0.0295 (14)
H8−0.15760.62360.61810.035*
C90.0549 (6)0.6536 (9)0.7084 (3)0.0469 (19)
H9A0.12010.71620.71020.070*
H9B0.07700.55040.70400.070*
H9C0.01270.66490.74430.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.027 (3)0.019 (4)0.039 (4)0.001 (3)0.009 (2)0.002 (3)
C20.028 (4)0.028 (5)0.044 (7)−0.002 (4)0.000 (5)0.002 (5)
C30.043 (5)0.023 (6)0.042 (8)−0.010 (4)−0.015 (5)−0.006 (5)
C100.034 (6)0.023 (5)0.034 (7)−0.001 (4)0.008 (5)0.003 (5)
Cl10.024 (2)0.049 (4)0.148 (11)−0.008 (2)−0.010 (4)0.028 (5)
Cl50.097 (6)0.031 (3)0.063 (5)0.004 (4)0.054 (5)0.002 (3)
C1B0.027 (3)0.019 (4)0.039 (4)0.001 (3)0.009 (2)0.002 (3)
C2B0.027 (5)0.032 (7)0.037 (8)−0.005 (5)0.001 (5)0.010 (6)
C3B0.044 (6)0.028 (7)0.037 (9)−0.008 (5)−0.011 (6)−0.008 (6)
C10B0.036 (8)0.031 (6)0.033 (8)0.006 (6)0.008 (6)0.001 (6)
Cl1B0.026 (3)0.070 (10)0.120 (12)−0.009 (5)−0.013 (5)0.060 (9)
Cl5B0.091 (9)0.077 (9)0.078 (10)0.056 (7)0.062 (8)0.031 (7)
Cl20.0420 (9)0.0262 (8)0.0426 (9)0.0103 (7)0.0038 (7)0.0046 (7)
Cl30.0581 (12)0.0293 (9)0.0577 (12)−0.0116 (8)0.0108 (9)0.0093 (8)
Cl40.0378 (9)0.0703 (13)0.0475 (10)0.0127 (9)0.0193 (8)0.0182 (10)
C40.038 (3)0.031 (3)0.033 (3)0.004 (3)−0.003 (3)−0.003 (3)
C50.024 (3)0.024 (3)0.030 (3)0.003 (2)−0.001 (2)0.002 (2)
C60.039 (3)0.028 (3)0.025 (3)0.002 (3)0.003 (3)0.001 (3)
C70.028 (3)0.022 (3)0.030 (3)0.000 (2)−0.002 (3)0.000 (2)
C80.022 (3)0.033 (3)0.034 (3)−0.004 (3)0.002 (3)0.008 (3)
C90.041 (4)0.045 (4)0.055 (5)−0.005 (3)−0.022 (4)0.013 (4)

Geometric parameters (Å, °)

C1—C101.507 (13)C10B—Cl5B1.811 (14)
C1—C21.550 (14)C10B—H10C0.9900
C1—C61.553 (12)C10B—H10D0.9900
C1—C71.60 (3)Cl2—C51.807 (6)
C2—C31.556 (16)Cl3—C81.796 (7)
C2—Cl11.808 (11)Cl4—C81.760 (7)
C2—H21.0000C4—C51.533 (9)
C3—C41.550 (13)C4—C71.556 (9)
C3—H3A0.9900C4—H4B1.0000
C3—H3B0.9900C4—H4A1.0000
C10—Cl51.806 (11)C5—C61.549 (8)
C10—H10A0.9900C5—H51.0000
C10—H10B0.9900C6—H6C0.9900
C1B—C10B1.515 (15)C6—H6D0.9900
C1B—C71.55 (3)C6—H6A0.9900
C1B—C2B1.557 (15)C6—H6B0.9900
C1B—C61.569 (15)C7—C91.519 (9)
C2B—C3B1.542 (18)C7—C81.538 (8)
C2B—Cl1B1.798 (14)C8—H81.0000
C2B—H2B1.0000C9—H9A0.9800
C3B—C41.519 (15)C9—H9B0.9800
C3B—H3B10.9900C9—H9C0.9800
C3B—H3B20.9900
C10—C1—C2116.8 (15)C3B—C4—H4B110.9
C10—C1—C6110.9 (13)C5—C4—H4B110.9
C2—C1—C698.5 (11)C3—C4—H4B125.7
C10—C1—C7121.5 (14)C7—C4—H4B110.9
C2—C1—C7104.4 (12)C3B—C4—H4A100.9
C6—C1—C7101.3 (12)C5—C4—H4A116.2
C1—C2—C3100.8 (11)C3—C4—H4A115.7
C1—C2—Cl1111.3 (11)C7—C4—H4A116.2
C3—C2—Cl1112.9 (12)C4—C5—C6103.0 (5)
C1—C2—H2110.5C4—C5—Cl2113.9 (4)
C3—C2—H2110.5C6—C5—Cl2111.7 (4)
Cl1—C2—H2110.5C4—C5—H5109.3
C4—C3—C2108.0 (11)C6—C5—H5109.3
C4—C3—H3A110.1Cl2—C5—H5109.3
C2—C3—H3A110.1C5—C6—C1105.8 (9)
C4—C3—H3B110.1C5—C6—C1B100.4 (12)
C2—C3—H3B110.1C5—C6—H6C111.7
H3A—C3—H3B108.4C1—C6—H6C113.4
C1—C10—Cl5112.1 (13)C1B—C6—H6C111.7
C1—C10—H10A109.2C5—C6—H6D111.7
Cl5—C10—H10A109.2C1—C6—H6D104.6
C1—C10—H10B109.2C1B—C6—H6D111.7
Cl5—C10—H10B109.2H6C—C6—H6D109.5
H10A—C10—H10B107.9C5—C6—H6A110.6
C10B—C1B—C7109.9 (18)C1—C6—H6A110.6
C10B—C1B—C2B113.7 (18)C1B—C6—H6A108.5
C7—C1B—C2B99.7 (16)H6D—C6—H6A113.2
C10B—C1B—C6118.4 (18)C5—C6—H6B110.4
C7—C1B—C6103.1 (16)C1—C6—H6B110.7
C2B—C1B—C6109.9 (15)C1B—C6—H6B117.9
C3B—C2B—C1B107.6 (15)H6C—C6—H6B104.9
C3B—C2B—Cl1B112.8 (16)H6A—C6—H6B108.7
C1B—C2B—Cl1B117.3 (15)C9—C7—C8109.2 (5)
C3B—C2B—H2B106.1C9—C7—C1B116.0 (7)
C1B—C2B—H2B106.1C8—C7—C1B116.5 (10)
Cl1B—C2B—H2B106.1C9—C7—C4112.8 (6)
C4—C3B—C2B96.3 (14)C8—C7—C4111.8 (5)
C4—C3B—H3B1112.5C1B—C7—C489.2 (9)
C2B—C3B—H3B1112.5C9—C7—C1117.3 (7)
C4—C3B—H3B2112.5C8—C7—C1110.1 (8)
C2B—C3B—H3B2112.5C4—C7—C195.0 (7)
H3B1—C3B—H3B2110.0C7—C8—Cl4112.5 (5)
C1B—C10B—Cl5B108.0 (19)C7—C8—Cl3112.2 (4)
C1B—C10B—H10C110.1Cl4—C8—Cl3107.7 (3)
Cl5B—C10B—H10C110.1C7—C8—H8108.1
C1B—C10B—H10D110.1Cl4—C8—H8108.1
Cl5B—C10B—H10D110.1Cl3—C8—H8108.1
H10C—C10B—H10D108.4C7—C9—H9A109.5
C3B—C4—C5114.6 (13)C7—C9—H9B109.5
C5—C4—C3104.6 (10)H9A—C9—H9B109.5
C3B—C4—C7107.4 (12)C7—C9—H9C109.5
C5—C4—C7101.7 (5)H9A—C9—H9C109.5
C3—C4—C7100.2 (8)H9B—C9—H9C109.5
C10—C1—C2—C3−168.0 (16)C10B—C1B—C6—C121 (15)
C6—C1—C2—C373.3 (15)C7—C1B—C6—C1−100 (17)
C7—C1—C2—C3−30.7 (13)C2B—C1B—C6—C1154 (18)
C10—C1—C2—Cl1−48 (2)C10B—C1B—C7—C959.1 (17)
C6—C1—C2—Cl1−166.6 (12)C2B—C1B—C7—C9−60.6 (12)
C7—C1—C2—Cl189.3 (11)C6—C1B—C7—C9−173.8 (9)
C1—C2—C3—C4−3.0 (16)C10B—C1B—C7—C8−71.6 (16)
Cl1—C2—C3—C4−121.8 (13)C2B—C1B—C7—C8168.6 (9)
C2—C1—C10—Cl5−44 (2)C6—C1B—C7—C855.4 (15)
C6—C1—C10—Cl567.4 (18)C10B—C1B—C7—C4174.3 (15)
C7—C1—C10—Cl5−173.8 (11)C2B—C1B—C7—C454.5 (10)
C10B—C1B—C2B—C3B−154 (2)C6—C1B—C7—C4−58.7 (12)
C7—C1B—C2B—C3B−37.6 (18)C10B—C1B—C7—C1−43 (6)
C6—C1B—C2B—C3B70 (2)C2B—C1B—C7—C1−162 (7)
C10B—C1B—C2B—Cl1B−26 (3)C6—C1B—C7—C184 (6)
C7—C1B—C2B—Cl1B90.8 (16)C3B—C4—C7—C957.4 (14)
C6—C1B—C2B—Cl1B−161.4 (17)C5—C4—C7—C9178.1 (6)
C1B—C2B—C3B—C40(2)C3—C4—C7—C970.8 (11)
Cl1B—C2B—C3B—C4−130.7 (17)C3B—C4—C7—C8−179.0 (13)
C7—C1B—C10B—Cl5B−179.7 (13)C5—C4—C7—C8−58.3 (7)
C2B—C1B—C10B—Cl5B−69 (3)C3—C4—C7—C8−165.7 (10)
C6—C1B—C10B—Cl5B62 (3)C3B—C4—C7—C1B−60.6 (13)
C2B—C3B—C4—C5−73.8 (18)C5—C4—C7—C1B60.1 (8)
C2B—C3B—C4—C3−24 (6)C3—C4—C7—C1B−47.3 (11)
C2B—C3B—C4—C738.4 (18)C3B—C4—C7—C1−65.0 (13)
C2—C3—C4—C3B157 (8)C5—C4—C7—C155.8 (7)
C2—C3—C4—C5−68.9 (14)C3—C4—C7—C1−51.6 (10)
C2—C3—C4—C736.2 (14)C10—C1—C7—C968.3 (15)
C3B—C4—C5—C674.6 (13)C2—C1—C7—C9−66.4 (10)
C3—C4—C5—C663.0 (9)C6—C1—C7—C9−168.4 (7)
C7—C4—C5—C6−40.9 (6)C10—C1—C7—C8−57.4 (14)
C3B—C4—C5—Cl2−46.6 (13)C2—C1—C7—C8167.8 (8)
C3—C4—C5—Cl2−58.2 (9)C6—C1—C7—C865.9 (10)
C7—C4—C5—Cl2−162.1 (4)C10—C1—C7—C1B150 (7)
C4—C5—C6—C18.1 (10)C2—C1—C7—C1B15 (6)
Cl2—C5—C6—C1130.7 (9)C6—C1—C7—C1B−87 (6)
C4—C5—C6—C1B2.7 (13)C10—C1—C7—C4−172.8 (13)
Cl2—C5—C6—C1B125.4 (12)C2—C1—C7—C452.4 (9)
C10—C1—C6—C5156.8 (13)C6—C1—C7—C4−49.5 (9)
C2—C1—C6—C5−80.2 (13)C9—C7—C8—Cl468.6 (6)
C7—C1—C6—C526.4 (11)C1B—C7—C8—Cl4−157.5 (8)
C10—C1—C6—C1B−159 (18)C4—C7—C8—Cl4−56.9 (6)
C2—C1—C6—C1B−36 (16)C1—C7—C8—Cl4−161.2 (6)
C7—C1—C6—C1B71 (16)C9—C7—C8—Cl3−53.0 (7)
C10B—C1B—C6—C5158 (2)C1B—C7—C8—Cl380.9 (9)
C7—C1B—C6—C536.6 (14)C4—C7—C8—Cl3−178.5 (4)
C2B—C1B—C6—C5−69 (2)C1—C7—C8—Cl377.2 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2100).

References

  • Blessing, R. H. (1995). Acta Cryst. A51, 33–38. [PubMed]
  • Bruker (2004). COLLECT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst.36, 1103.
  • Duisenberg, A. J. M. (1992). J. Appl. Cryst.25, 92–96.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Jennings, B. H. & Herschbach, G. B. (1965). J. Org. Chem.30, 3902–3909.
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.39, 453–457.
  • Nikiforov, V. A., Karavan, V. S. & Miltsov, S. A. (1999). Organohalogen Compd, 41, 605–609.
  • Nikiforov, V. A., Karavan, V. S. & Miltsov, S. A. (2000). Chemosphere, 41, 467–472. [PubMed]
  • Nikiforov, V. A., Karavan, V. S. & Miltsov, S. A. (2001). Organohalogen Compd, 50, 268–271.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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