(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undeca­chloro­penta­cyclo­[12.2.1.16,9.02,13.05,10]octa­deca-7,15-diene

Riddell, N.; McCrindle, R.; Arsenault, G.; Lough, A.J.

doi:10.1107/S160053680801622X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1250

doi:10.1107/S160053680801622X

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(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undecachloropentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadeca-7,15-diene

Nicole Riddell,^a Robert McCrindle,^b Gilles Arsenault ^a and Alan J Lough ^c ^*

^aWellington Laboratories, Research Division, Guelph, Ontario, Canada N1G 3M5, ^bDepartment of Chemistry, University of Guelph, Ontario, Canada N1G 2W1, and ^cDepartment of Chemistry, University of Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 20 May 2008; accepted 28 May 2008; online 13 June 2008)

The title compound, C₁₈H₁₃Cl₁₁, is an undecachlorinated commercial flame retardant. The asymmetric unit contains two independent half-molecules. The complete molecules are generated by crystallographic inversion symmetry, causing the terminal H atoms and one of the Cl atoms to be disordered equally over two sites in each molecule. The central eight-membered rings are in chair-type conformations. In the crystal structure, there is a single weak intermolecular C—H⋯Cl hydrogen bond.

Related literature

For related literature, see: Riddell et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₃Cl₁₁
M_r = 619.23
Monoclinic, P 2₁ /c
a = 13.3129 (5) Å
b = 12.1263 (6) Å
c = 14.7229 (7) Å
β = 99.505 (3)°
V = 2344.18 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.31 mm⁻¹
T = 150 (1) K
0.26 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.715, T_max = 0.825
15654 measured reflections
5338 independent reflections
3481 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.118
S = 1.05
5338 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1B—H1B⋯Cl4Aⁱ	1.00	2.70	3.656 (4)	160
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO–SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801622X/pk2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801622X/pk2101Isup2.hkl

checkCIF report

Comment top

For background information and related references see the previous paper (Riddell et al., 2008). Dechlorane Plus (DP) is a commercial chlorinated flame retardant used in styrenic plastics (http://www.inchem.org/documents/ehc/ehc/ehc192.htm) to protect human life and property against fires. We have synthesized the dechlorinated compound (1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18- undecachloropentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]-octadeca-7,15-diene. GC/MS and ¹H NMR spectroscopy have confirmed the basic structure of as having the DP-like structure with only 11 chlorine atoms. An NOE NMR experiment also strongly indicated that the proton on the bridging carbon atom was facing towards the cyclooctadiene ring since a positive through space interaction was observed. However, an X-ray structure determination was required to positively confirm the stereochemistry.

The asymmetric unit contains two independent half molecules. The symmetry complete molecules are generated by crystallographic inversion symmetry, causing atoms Cl6A and Cl6B, as well as the H atoms bonded to C9A and C9B to be disordered over two sites with equal occupancies. In both independent molecules the geometric parameters are the same within experimental error. The asymmetric unit is shown in Fig. 2. In the crystal structure there is a single weak intermolecular C—H···Cl interaction (Table 1).

Related literature top

For related literature, see: Riddell et al. (2008).

Experimental top

The synthesis of the title compound was carried out at Wellington Laboratories using proprietary methods. The compound was isolated and purified using chromatographic techniques. For single-crystal x-ray crystallography, colourless crystals were grown from a solution in toluene.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. The disorder is not shown and the atoms labeled with lower case suffixes a and b are related by the symmetry operators (-x, -y+1, -z+1) and (-x+1, - y+1, -z) respectively.

(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18- Undecachloropentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadeca-7,15-diene top

Crystal data top

C₁₈H₁₃Cl₁₁	F(000) = 1232
M_r = 619.23	D_x = 1.755 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15654 reflections
a = 13.3129 (5) Å	θ = 2.8–27.5°
b = 12.1263 (6) Å	µ = 1.31 mm⁻¹
c = 14.7229 (7) Å	T = 150 K
β = 99.505 (3)°	Block, colourless
V = 2344.18 (18) Å³	0.26 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	5338 independent reflections
Radiation source: fine-focus sealed tube	3481 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
ϕ scans and ω scans with κ offsets	h = −17→17
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→15
T_min = 0.715, T_max = 0.825	l = −16→19
15654 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0314P)² + 4.5718P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
5338 reflections	Δρ_max = 0.53 e Å⁻³
272 parameters	Δρ_min = −0.68 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0011 (3)

Crystal data top

C₁₈H₁₃Cl₁₁	V = 2344.18 (18) Å³
M_r = 619.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3129 (5) Å	µ = 1.31 mm⁻¹
b = 12.1263 (6) Å	T = 150 K
c = 14.7229 (7) Å	0.26 × 0.20 × 0.15 mm
β = 99.505 (3)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	5338 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3481 reflections with I > 2σ(I)
T_min = 0.715, T_max = 0.825	R_int = 0.052
15654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	Δρ_max = 0.53 e Å⁻³
5338 reflections	Δρ_min = −0.68 e Å⁻³
272 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1A	0.12630 (8)	0.59357 (8)	0.23239 (6)	0.0351 (3)
Cl2A	−0.04105 (8)	0.77914 (9)	0.28215 (7)	0.0390 (3)
Cl3A	0.03958 (8)	0.87394 (8)	0.49922 (7)	0.0371 (3)
Cl4A	0.25958 (7)	0.75232 (9)	0.58340 (7)	0.0375 (3)
Cl5A	0.28655 (8)	0.77926 (10)	0.35627 (7)	0.0449 (3)
Cl6A	0.32477 (14)	0.57426 (16)	0.42481 (15)	0.0351 (5)	0.50
C1A	0.0896 (3)	0.5390 (3)	0.4083 (2)	0.0235 (8)
H1A	0.1293	0.4710	0.3993	0.028*
C2A	0.1294 (3)	0.5849 (3)	0.5085 (2)	0.0229 (8)
H2A	0.1854	0.5355	0.5384	0.027*
C3A	0.0525 (3)	0.5978 (3)	0.5746 (2)	0.0246 (8)
H3A1	−0.0099	0.6331	0.5412	0.030*
H3A2	0.0817	0.6477	0.6254	0.030*
C4A	−0.0227 (3)	0.5119 (3)	0.3837 (2)	0.0268 (8)
H4A1	−0.0412	0.5080	0.3158	0.032*
H4A2	−0.0626	0.5724	0.4054	0.032*
C5A	0.1236 (3)	0.6328 (3)	0.3464 (2)	0.0255 (8)
C6A	0.0612 (3)	0.7346 (3)	0.3593 (3)	0.0263 (8)
C7A	0.0923 (3)	0.7720 (3)	0.4438 (3)	0.0243 (8)
C8A	0.1776 (3)	0.6973 (3)	0.4878 (2)	0.0245 (8)
C9A	0.2268 (3)	0.6680 (3)	0.4039 (3)	0.0289 (9)
H9C	0.2739	0.6037	0.4170	0.035*	0.50
Cl1B	0.50434 (8)	0.70192 (12)	0.26767 (8)	0.0573 (4)
Cl2B	0.68792 (8)	0.51251 (11)	0.29107 (7)	0.0488 (3)
Cl3B	0.83732 (7)	0.55922 (9)	0.12642 (7)	0.0400 (3)
Cl4B	0.74566 (9)	0.77648 (10)	0.00260 (9)	0.0501 (3)
Cl5B	0.70173 (9)	0.85653 (11)	0.21603 (10)	0.0647 (4)
Cl6B	0.52623 (17)	0.8699 (2)	0.0840 (2)	0.0609 (8)	0.50
C1B	0.5100 (3)	0.6208 (3)	0.0915 (3)	0.0312 (9)
H1B	0.4460	0.6647	0.0747	0.037*
C2B	0.5781 (3)	0.6426 (3)	0.0152 (3)	0.0306 (9)
H2B	0.5410	0.6952	−0.0308	0.037*
C3B	0.6089 (3)	0.5433 (3)	−0.0368 (3)	0.0310 (9)
H3B1	0.6333	0.4843	0.0079	0.037*
H3B2	0.6663	0.5644	−0.0683	0.037*
C4B	0.4792 (3)	0.5024 (3)	0.1091 (3)	0.0304 (9)
H4B1	0.4586	0.4988	0.1706	0.037*
H4B2	0.5394	0.4542	0.1104	0.037*
C5B	0.5738 (3)	0.6757 (4)	0.1780 (3)	0.0362 (10)
C6B	0.6701 (3)	0.6059 (4)	0.2039 (3)	0.0344 (10)
C7B	0.7274 (3)	0.6241 (3)	0.1398 (3)	0.0324 (9)
C8B	0.6712 (3)	0.7049 (3)	0.0715 (3)	0.0343 (9)
C9B	0.6180 (3)	0.7760 (4)	0.1363 (3)	0.0444 (11)
H9D	0.5630	0.8225	0.1008	0.053*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.0514 (6)	0.0324 (5)	0.0245 (5)	−0.0025 (5)	0.0149 (4)	−0.0003 (4)
Cl2A	0.0392 (6)	0.0357 (6)	0.0398 (6)	0.0080 (5)	−0.0005 (4)	0.0127 (5)
Cl3A	0.0473 (6)	0.0243 (5)	0.0446 (6)	0.0049 (5)	0.0217 (5)	−0.0033 (4)
Cl4A	0.0297 (5)	0.0500 (7)	0.0331 (5)	−0.0137 (5)	0.0057 (4)	−0.0082 (5)
Cl5A	0.0406 (6)	0.0562 (7)	0.0428 (6)	−0.0200 (5)	0.0212 (5)	−0.0039 (5)
Cl6A	0.0289 (10)	0.0275 (10)	0.0519 (13)	0.0056 (8)	0.0154 (9)	0.0000 (9)
C1A	0.0272 (18)	0.0192 (19)	0.025 (2)	0.0036 (16)	0.0068 (15)	0.0029 (15)
C2A	0.0234 (18)	0.0228 (19)	0.0222 (19)	0.0048 (16)	0.0031 (15)	−0.0005 (15)
C3A	0.0278 (19)	0.024 (2)	0.0225 (19)	−0.0043 (16)	0.0055 (15)	0.0007 (16)
C4A	0.034 (2)	0.026 (2)	0.0194 (19)	−0.0004 (17)	0.0010 (16)	0.0025 (16)
C5A	0.033 (2)	0.024 (2)	0.0217 (19)	0.0011 (17)	0.0105 (16)	0.0037 (16)
C6A	0.0250 (19)	0.024 (2)	0.031 (2)	−0.0031 (16)	0.0074 (16)	0.0079 (16)
C7A	0.0302 (19)	0.0164 (18)	0.029 (2)	−0.0018 (16)	0.0139 (16)	−0.0012 (15)
C8A	0.0234 (18)	0.028 (2)	0.0231 (19)	−0.0042 (16)	0.0059 (15)	−0.0017 (16)
C9A	0.0264 (19)	0.031 (2)	0.031 (2)	0.0052 (17)	0.0111 (16)	0.0046 (17)
Cl1B	0.0337 (6)	0.0861 (10)	0.0536 (8)	0.0007 (6)	0.0119 (5)	−0.0381 (7)
Cl2B	0.0441 (6)	0.0722 (9)	0.0271 (6)	0.0022 (6)	−0.0024 (5)	0.0005 (5)
Cl3B	0.0233 (5)	0.0504 (7)	0.0458 (6)	0.0043 (5)	0.0042 (4)	−0.0118 (5)
Cl4B	0.0484 (7)	0.0451 (7)	0.0570 (8)	−0.0176 (6)	0.0088 (5)	−0.0010 (6)
Cl5B	0.0413 (6)	0.0622 (8)	0.0884 (10)	−0.0096 (6)	0.0042 (6)	−0.0458 (8)
Cl6B	0.0358 (12)	0.0373 (13)	0.100 (2)	0.0108 (10)	−0.0158 (12)	−0.0205 (13)
C1B	0.0195 (18)	0.040 (2)	0.032 (2)	0.0056 (18)	−0.0011 (16)	−0.0101 (19)
C2B	0.0257 (19)	0.030 (2)	0.034 (2)	0.0015 (17)	−0.0028 (17)	−0.0019 (17)
C3B	0.0255 (19)	0.038 (2)	0.028 (2)	−0.0051 (18)	0.0023 (16)	−0.0041 (18)
C4B	0.0238 (19)	0.042 (2)	0.025 (2)	−0.0002 (18)	0.0016 (15)	−0.0035 (18)
C5B	0.0232 (19)	0.048 (3)	0.038 (2)	0.0026 (19)	0.0056 (17)	−0.016 (2)
C6B	0.027 (2)	0.050 (3)	0.024 (2)	0.0022 (19)	−0.0012 (16)	−0.0133 (19)
C7B	0.0218 (19)	0.041 (2)	0.033 (2)	0.0013 (18)	−0.0002 (16)	−0.0141 (19)
C8B	0.029 (2)	0.033 (2)	0.039 (2)	−0.0032 (18)	0.0017 (18)	−0.0076 (19)
C9B	0.031 (2)	0.041 (3)	0.058 (3)	0.006 (2)	−0.004 (2)	−0.017 (2)

Geometric parameters (Å, º) top

Cl1A—C5A	1.751 (4)	Cl1B—C5B	1.761 (4)
Cl2A—C6A	1.710 (4)	Cl2B—C6B	1.698 (4)
Cl3A—C7A	1.696 (4)	Cl3B—C7B	1.701 (4)
Cl4A—C8A	1.763 (4)	Cl4B—C8B	1.760 (4)
Cl5A—C9A	1.769 (4)	Cl5B—C9B	1.772 (4)
Cl6A—C9A	1.720 (4)	Cl6B—C9B	1.752 (5)
C1A—C4A	1.515 (5)	C1B—C4B	1.527 (6)
C1A—C5A	1.570 (5)	C1B—C5B	1.559 (5)
C1A—C2A	1.584 (5)	C1B—C2B	1.579 (5)
C1A—H1A	1.0000	C1B—H1B	1.0000
C2A—C3A	1.533 (5)	C2B—C3B	1.518 (5)
C2A—C8A	1.558 (5)	C2B—C8B	1.567 (5)
C2A—H2A	1.0000	C2B—H2B	1.0000
C3A—C4Aⁱ	1.544 (5)	C3B—C4Bⁱⁱ	1.551 (5)
C3A—H3A1	0.9900	C3B—H3B1	0.9900
C3A—H3A2	0.9900	C3B—H3B2	0.9900
C4A—C3Aⁱ	1.544 (5)	C4B—C3Bⁱⁱ	1.551 (5)
C4A—H4A1	0.9900	C4B—H4B1	0.9900
C4A—H4A2	0.9900	C4B—H4B2	0.9900
C5A—C6A	1.518 (5)	C5B—C9B	1.524 (7)
C5A—C9A	1.548 (5)	C5B—C6B	1.531 (6)
C6A—C7A	1.324 (5)	C6B—C7B	1.328 (5)
C7A—C8A	1.512 (5)	C7B—C8B	1.511 (6)
C8A—C9A	1.533 (5)	C8B—C9B	1.542 (6)

C4A—C1A—C5A	112.7 (3)	C4B—C1B—C5B	112.8 (3)
C4A—C1A—C2A	117.6 (3)	C4B—C1B—C2B	118.7 (3)
C5A—C1A—C2A	101.6 (3)	C5B—C1B—C2B	102.2 (3)
C4A—C1A—H1A	108.1	C4B—C1B—H1B	107.5
C5A—C1A—H1A	108.1	C5B—C1B—H1B	107.5
C2A—C1A—H1A	108.1	C2B—C1B—H1B	107.5
C3A—C2A—C8A	112.0 (3)	C3B—C2B—C8B	113.2 (3)
C3A—C2A—C1A	118.2 (3)	C3B—C2B—C1B	117.4 (3)
C8A—C2A—C1A	102.2 (3)	C8B—C2B—C1B	101.6 (3)
C3A—C2A—H2A	108.0	C3B—C2B—H2B	108.1
C8A—C2A—H2A	108.0	C8B—C2B—H2B	108.1
C1A—C2A—H2A	108.0	C1B—C2B—H2B	108.1
C2A—C3A—C4Aⁱ	114.1 (3)	C2B—C3B—C4Bⁱⁱ	113.1 (3)
C2A—C3A—H3A1	108.7	C2B—C3B—H3B1	109.0
C4Aⁱ—C3A—H3A1	108.7	C4Bⁱⁱ—C3B—H3B1	109.0
C2A—C3A—H3A2	108.7	C2B—C3B—H3B2	109.0
C4Aⁱ—C3A—H3A2	108.7	C4Bⁱⁱ—C3B—H3B2	109.0
H3A1—C3A—H3A2	107.6	H3B1—C3B—H3B2	107.8
C1A—C4A—C3Aⁱ	113.6 (3)	C1B—C4B—C3Bⁱⁱ	114.4 (3)
C1A—C4A—H4A1	108.8	C1B—C4B—H4B1	108.7
C3Aⁱ—C4A—H4A1	108.8	C3Bⁱⁱ—C4B—H4B1	108.7
C1A—C4A—H4A2	108.8	C1B—C4B—H4B2	108.7
C3Aⁱ—C4A—H4A2	108.8	C3Bⁱⁱ—C4B—H4B2	108.7
H4A1—C4A—H4A2	107.7	H4B1—C4B—H4B2	107.6
C6A—C5A—C9A	99.3 (3)	C9B—C5B—C6B	100.3 (3)
C6A—C5A—C1A	107.5 (3)	C9B—C5B—C1B	101.9 (3)
C9A—C5A—C1A	101.4 (3)	C6B—C5B—C1B	106.8 (3)
C6A—C5A—Cl1A	116.0 (3)	C9B—C5B—Cl1B	116.3 (3)
C9A—C5A—Cl1A	116.2 (2)	C6B—C5B—Cl1B	115.8 (3)
C1A—C5A—Cl1A	114.4 (3)	C1B—C5B—Cl1B	114.0 (3)
C7A—C6A—C5A	107.6 (3)	C7B—C6B—C5B	106.7 (4)
C7A—C6A—Cl2A	127.4 (3)	C7B—C6B—Cl2B	128.5 (3)
C5A—C6A—Cl2A	124.5 (3)	C5B—C6B—Cl2B	124.3 (3)
C6A—C7A—C8A	107.1 (3)	C6B—C7B—C8B	107.5 (3)
C6A—C7A—Cl3A	127.7 (3)	C6B—C7B—Cl3B	127.8 (4)
C8A—C7A—Cl3A	124.8 (3)	C8B—C7B—Cl3B	124.4 (3)
C7A—C8A—C9A	100.6 (3)	C7B—C8B—C9B	100.3 (3)
C7A—C8A—C2A	107.6 (3)	C7B—C8B—C2B	107.5 (3)
C9A—C8A—C2A	101.5 (3)	C9B—C8B—C2B	101.2 (3)
C7A—C8A—Cl4A	116.0 (3)	C7B—C8B—Cl4B	116.0 (3)
C9A—C8A—Cl4A	116.2 (3)	C9B—C8B—Cl4B	116.2 (3)
C2A—C8A—Cl4A	113.3 (3)	C2B—C8B—Cl4B	113.8 (3)
C8A—C9A—C5A	92.6 (3)	C5B—C9B—C8B	92.9 (3)
C8A—C9A—Cl6A	114.9 (3)	C5B—C9B—Cl6B	114.1 (3)
C5A—C9A—Cl6A	119.6 (3)	C8B—C9B—Cl6B	116.7 (3)
C8A—C9A—Cl5A	115.0 (3)	C5B—C9B—Cl5B	114.6 (3)
C5A—C9A—Cl5A	114.2 (3)	C8B—C9B—Cl5B	114.5 (3)
Cl6A—C9A—Cl5A	101.4 (2)	Cl6B—C9B—Cl5B	104.5 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1B—H1B···Cl4Aⁱⁱⁱ	1.00	2.70	3.656 (4)	160

Symmetry code: (iii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Cl₁₁
M_r	619.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	13.3129 (5), 12.1263 (6), 14.7229 (7)
β (°)	99.505 (3)
V (Å³)	2344.18 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.26 × 0.20 × 0.15

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.715, 0.825
No. of measured, independent and observed [I > 2σ(I)] reflections	15654, 5338, 3481
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.118, 1.05
No. of reflections	5338
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.68

Computer programs: COLLECT (Nonius, 2002), DENZO–SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1B—H1B···Cl4Aⁱ	1.00	2.70	3.656 (4)	160

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors acknowledge NSERC Canada and the University of Toronto for funding.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Riddell, N., McCrindle, R., Arsenault, G. & Lough, A. J. (2008). Acta Cryst. E64, o1249. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 7| July 2008| Page o1250

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undeca­chloro­penta­cyclo­[12.2.1.16,9.02,13.05,10]octa­deca-7,15-diene

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undecachloropentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadeca-7,15-diene