Literature DB >> 21202884

(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undeca-chloro-penta-cyclo-[12.2.1.1.0.0]octa-deca-7,15-diene.

Nicole Riddell, Robert McCrindle, Gilles Arsenault, Alan J Lough.   

Abstract

The title compound, C(18)H(13)Cl(11), is an undecachlorinated commercial flame retardant. The asymmetric unit contains two independent half-mol-ecules. The complete mol-ecules 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 mol-ecule. The central eight-membered rings are in chair-type conformations. In the crystal structure, there is a single weak inter-molecular C-H⋯Cl hydrogen bond.

Entities:  

Year:  2008        PMID： 21202884      PMCID： PMC2961815          DOI： 10.1107/S160053680801622X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C18H13Cl11 M = 619.23 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.118 S = 1.05 5338 reflections 272 parameters H-atom parameters constrained Δρmax = 0.53 e Å−3 Δρmin = −0.68 e Å−3 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801622X/pk2101sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680801622X/pk2101Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H13Cl11F000 = 1232
Mr = 619.23Dx = 1.755 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15654 reflections
a = 13.3129 (5) Åθ = 2.8–27.5º
b = 12.1263 (6) ŵ = 1.31 mm−1
c = 14.7229 (7) ÅT = 150 (1) K
β = 99.505 (3)ºBlock, colourless
V = 2344.18 (18) Å30.26 × 0.20 × 0.15 mm
Z = 4
Bruker–Nonius KappaCCD diffractometer5338 independent reflections
Radiation source: fine-focus sealed tube3481 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.052
Detector resolution: 9 pixels mm-1θmax = 27.5º
T = 150(2) Kθmin = 2.8º
φ scans and ω scans with κ offsetsh = −17→17
Absorption correction: multi-scan(SORTAV; Blessing, 1995)k = −14→15
Tmin = 0.715, Tmax = 0.825l = −16→19
15654 measured reflections
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050  w = 1/[σ2(Fo2) + (0.0314P)2 + 4.5718P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.118(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.53 e Å−3
5338 reflectionsΔρmin = −0.68 e Å−3
272 parametersExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0011 (3)
Secondary atom site location: difference Fourier map
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.
xyzUiso*/UeqOcc. (<1)
Cl1A0.12630 (8)0.59357 (8)0.23239 (6)0.0351 (3)
Cl2A−0.04105 (8)0.77914 (9)0.28215 (7)0.0390 (3)
Cl3A0.03958 (8)0.87394 (8)0.49922 (7)0.0371 (3)
Cl4A0.25958 (7)0.75232 (9)0.58340 (7)0.0375 (3)
Cl5A0.28655 (8)0.77926 (10)0.35627 (7)0.0449 (3)
Cl6A0.32477 (14)0.57426 (16)0.42481 (15)0.0351 (5)0.50
C1A0.0896 (3)0.5390 (3)0.4083 (2)0.0235 (8)
H1A0.12930.47100.39930.028*
C2A0.1294 (3)0.5849 (3)0.5085 (2)0.0229 (8)
H2A0.18540.53550.53840.027*
C3A0.0525 (3)0.5978 (3)0.5746 (2)0.0246 (8)
H3A1−0.00990.63310.54120.030*
H3A20.08170.64770.62540.030*
C4A−0.0227 (3)0.5119 (3)0.3837 (2)0.0268 (8)
H4A1−0.04120.50800.31580.032*
H4A2−0.06260.57240.40540.032*
C5A0.1236 (3)0.6328 (3)0.3464 (2)0.0255 (8)
C6A0.0612 (3)0.7346 (3)0.3593 (3)0.0263 (8)
C7A0.0923 (3)0.7720 (3)0.4438 (3)0.0243 (8)
C8A0.1776 (3)0.6973 (3)0.4878 (2)0.0245 (8)
C9A0.2268 (3)0.6680 (3)0.4039 (3)0.0289 (9)
H9C0.27390.60370.41700.035*0.50
Cl1B0.50434 (8)0.70192 (12)0.26767 (8)0.0573 (4)
Cl2B0.68792 (8)0.51251 (11)0.29107 (7)0.0488 (3)
Cl3B0.83732 (7)0.55922 (9)0.12642 (7)0.0400 (3)
Cl4B0.74566 (9)0.77648 (10)0.00260 (9)0.0501 (3)
Cl5B0.70173 (9)0.85653 (11)0.21603 (10)0.0647 (4)
Cl6B0.52623 (17)0.8699 (2)0.0840 (2)0.0609 (8)0.50
C1B0.5100 (3)0.6208 (3)0.0915 (3)0.0312 (9)
H1B0.44600.66470.07470.037*
C2B0.5781 (3)0.6426 (3)0.0152 (3)0.0306 (9)
H2B0.54100.6952−0.03080.037*
C3B0.6089 (3)0.5433 (3)−0.0368 (3)0.0310 (9)
H3B10.63330.48430.00790.037*
H3B20.66630.5644−0.06830.037*
C4B0.4792 (3)0.5024 (3)0.1091 (3)0.0304 (9)
H4B10.45860.49880.17060.037*
H4B20.53940.45420.11040.037*
C5B0.5738 (3)0.6757 (4)0.1780 (3)0.0362 (10)
C6B0.6701 (3)0.6059 (4)0.2039 (3)0.0344 (10)
C7B0.7274 (3)0.6241 (3)0.1398 (3)0.0324 (9)
C8B0.6712 (3)0.7049 (3)0.0715 (3)0.0343 (9)
C9B0.6180 (3)0.7760 (4)0.1363 (3)0.0444 (11)
H9D0.56300.82250.10080.053*0.50
U11U22U33U12U13U23
Cl1A0.0514 (6)0.0324 (5)0.0245 (5)−0.0025 (5)0.0149 (4)−0.0003 (4)
Cl2A0.0392 (6)0.0357 (6)0.0398 (6)0.0080 (5)−0.0005 (4)0.0127 (5)
Cl3A0.0473 (6)0.0243 (5)0.0446 (6)0.0049 (5)0.0217 (5)−0.0033 (4)
Cl4A0.0297 (5)0.0500 (7)0.0331 (5)−0.0137 (5)0.0057 (4)−0.0082 (5)
Cl5A0.0406 (6)0.0562 (7)0.0428 (6)−0.0200 (5)0.0212 (5)−0.0039 (5)
Cl6A0.0289 (10)0.0275 (10)0.0519 (13)0.0056 (8)0.0154 (9)0.0000 (9)
C1A0.0272 (18)0.0192 (19)0.025 (2)0.0036 (16)0.0068 (15)0.0029 (15)
C2A0.0234 (18)0.0228 (19)0.0222 (19)0.0048 (16)0.0031 (15)−0.0005 (15)
C3A0.0278 (19)0.024 (2)0.0225 (19)−0.0043 (16)0.0055 (15)0.0007 (16)
C4A0.034 (2)0.026 (2)0.0194 (19)−0.0004 (17)0.0010 (16)0.0025 (16)
C5A0.033 (2)0.024 (2)0.0217 (19)0.0011 (17)0.0105 (16)0.0037 (16)
C6A0.0250 (19)0.024 (2)0.031 (2)−0.0031 (16)0.0074 (16)0.0079 (16)
C7A0.0302 (19)0.0164 (18)0.029 (2)−0.0018 (16)0.0139 (16)−0.0012 (15)
C8A0.0234 (18)0.028 (2)0.0231 (19)−0.0042 (16)0.0059 (15)−0.0017 (16)
C9A0.0264 (19)0.031 (2)0.031 (2)0.0052 (17)0.0111 (16)0.0046 (17)
Cl1B0.0337 (6)0.0861 (10)0.0536 (8)0.0007 (6)0.0119 (5)−0.0381 (7)
Cl2B0.0441 (6)0.0722 (9)0.0271 (6)0.0022 (6)−0.0024 (5)0.0005 (5)
Cl3B0.0233 (5)0.0504 (7)0.0458 (6)0.0043 (5)0.0042 (4)−0.0118 (5)
Cl4B0.0484 (7)0.0451 (7)0.0570 (8)−0.0176 (6)0.0088 (5)−0.0010 (6)
Cl5B0.0413 (6)0.0622 (8)0.0884 (10)−0.0096 (6)0.0042 (6)−0.0458 (8)
Cl6B0.0358 (12)0.0373 (13)0.100 (2)0.0108 (10)−0.0158 (12)−0.0205 (13)
C1B0.0195 (18)0.040 (2)0.032 (2)0.0056 (18)−0.0011 (16)−0.0101 (19)
C2B0.0257 (19)0.030 (2)0.034 (2)0.0015 (17)−0.0028 (17)−0.0019 (17)
C3B0.0255 (19)0.038 (2)0.028 (2)−0.0051 (18)0.0023 (16)−0.0041 (18)
C4B0.0238 (19)0.042 (2)0.025 (2)−0.0002 (18)0.0016 (15)−0.0035 (18)
C5B0.0232 (19)0.048 (3)0.038 (2)0.0026 (19)0.0056 (17)−0.016 (2)
C6B0.027 (2)0.050 (3)0.024 (2)0.0022 (19)−0.0012 (16)−0.0133 (19)
C7B0.0218 (19)0.041 (2)0.033 (2)0.0013 (18)−0.0002 (16)−0.0141 (19)
C8B0.029 (2)0.033 (2)0.039 (2)−0.0032 (18)0.0017 (18)−0.0076 (19)
C9B0.031 (2)0.041 (3)0.058 (3)0.006 (2)−0.004 (2)−0.017 (2)
Cl1A—C5A1.751 (4)Cl1B—C5B1.761 (4)
Cl2A—C6A1.710 (4)Cl2B—C6B1.698 (4)
Cl3A—C7A1.696 (4)Cl3B—C7B1.701 (4)
Cl4A—C8A1.763 (4)Cl4B—C8B1.760 (4)
Cl5A—C9A1.769 (4)Cl5B—C9B1.772 (4)
Cl6A—C9A1.720 (4)Cl6B—C9B1.752 (5)
C1A—C4A1.515 (5)C1B—C4B1.527 (6)
C1A—C5A1.570 (5)C1B—C5B1.559 (5)
C1A—C2A1.584 (5)C1B—C2B1.579 (5)
C1A—H1A1.0000C1B—H1B1.0000
C2A—C3A1.533 (5)C2B—C3B1.518 (5)
C2A—C8A1.558 (5)C2B—C8B1.567 (5)
C2A—H2A1.0000C2B—H2B1.0000
C3A—C4Ai1.544 (5)C3B—C4Bii1.551 (5)
C3A—H3A10.9900C3B—H3B10.9900
C3A—H3A20.9900C3B—H3B20.9900
C4A—C3Ai1.544 (5)C4B—C3Bii1.551 (5)
C4A—H4A10.9900C4B—H4B10.9900
C4A—H4A20.9900C4B—H4B20.9900
C5A—C6A1.518 (5)C5B—C9B1.524 (7)
C5A—C9A1.548 (5)C5B—C6B1.531 (6)
C6A—C7A1.324 (5)C6B—C7B1.328 (5)
C7A—C8A1.512 (5)C7B—C8B1.511 (6)
C8A—C9A1.533 (5)C8B—C9B1.542 (6)
C4A—C1A—C5A112.7 (3)C4B—C1B—C5B112.8 (3)
C4A—C1A—C2A117.6 (3)C4B—C1B—C2B118.7 (3)
C5A—C1A—C2A101.6 (3)C5B—C1B—C2B102.2 (3)
C4A—C1A—H1A108.1C4B—C1B—H1B107.5
C5A—C1A—H1A108.1C5B—C1B—H1B107.5
C2A—C1A—H1A108.1C2B—C1B—H1B107.5
C3A—C2A—C8A112.0 (3)C3B—C2B—C8B113.2 (3)
C3A—C2A—C1A118.2 (3)C3B—C2B—C1B117.4 (3)
C8A—C2A—C1A102.2 (3)C8B—C2B—C1B101.6 (3)
C3A—C2A—H2A108.0C3B—C2B—H2B108.1
C8A—C2A—H2A108.0C8B—C2B—H2B108.1
C1A—C2A—H2A108.0C1B—C2B—H2B108.1
C2A—C3A—C4Ai114.1 (3)C2B—C3B—C4Bii113.1 (3)
C2A—C3A—H3A1108.7C2B—C3B—H3B1109.0
C4Ai—C3A—H3A1108.7C4Bii—C3B—H3B1109.0
C2A—C3A—H3A2108.7C2B—C3B—H3B2109.0
C4Ai—C3A—H3A2108.7C4Bii—C3B—H3B2109.0
H3A1—C3A—H3A2107.6H3B1—C3B—H3B2107.8
C1A—C4A—C3Ai113.6 (3)C1B—C4B—C3Bii114.4 (3)
C1A—C4A—H4A1108.8C1B—C4B—H4B1108.7
C3Ai—C4A—H4A1108.8C3Bii—C4B—H4B1108.7
C1A—C4A—H4A2108.8C1B—C4B—H4B2108.7
C3Ai—C4A—H4A2108.8C3Bii—C4B—H4B2108.7
H4A1—C4A—H4A2107.7H4B1—C4B—H4B2107.6
C6A—C5A—C9A99.3 (3)C9B—C5B—C6B100.3 (3)
C6A—C5A—C1A107.5 (3)C9B—C5B—C1B101.9 (3)
C9A—C5A—C1A101.4 (3)C6B—C5B—C1B106.8 (3)
C6A—C5A—Cl1A116.0 (3)C9B—C5B—Cl1B116.3 (3)
C9A—C5A—Cl1A116.2 (2)C6B—C5B—Cl1B115.8 (3)
C1A—C5A—Cl1A114.4 (3)C1B—C5B—Cl1B114.0 (3)
C7A—C6A—C5A107.6 (3)C7B—C6B—C5B106.7 (4)
C7A—C6A—Cl2A127.4 (3)C7B—C6B—Cl2B128.5 (3)
C5A—C6A—Cl2A124.5 (3)C5B—C6B—Cl2B124.3 (3)
C6A—C7A—C8A107.1 (3)C6B—C7B—C8B107.5 (3)
C6A—C7A—Cl3A127.7 (3)C6B—C7B—Cl3B127.8 (4)
C8A—C7A—Cl3A124.8 (3)C8B—C7B—Cl3B124.4 (3)
C7A—C8A—C9A100.6 (3)C7B—C8B—C9B100.3 (3)
C7A—C8A—C2A107.6 (3)C7B—C8B—C2B107.5 (3)
C9A—C8A—C2A101.5 (3)C9B—C8B—C2B101.2 (3)
C7A—C8A—Cl4A116.0 (3)C7B—C8B—Cl4B116.0 (3)
C9A—C8A—Cl4A116.2 (3)C9B—C8B—Cl4B116.2 (3)
C2A—C8A—Cl4A113.3 (3)C2B—C8B—Cl4B113.8 (3)
C8A—C9A—C5A92.6 (3)C5B—C9B—C8B92.9 (3)
C8A—C9A—Cl6A114.9 (3)C5B—C9B—Cl6B114.1 (3)
C5A—C9A—Cl6A119.6 (3)C8B—C9B—Cl6B116.7 (3)
C8A—C9A—Cl5A115.0 (3)C5B—C9B—Cl5B114.6 (3)
C5A—C9A—Cl5A114.2 (3)C8B—C9B—Cl5B114.5 (3)
Cl6A—C9A—Cl5A101.4 (2)Cl6B—C9B—Cl5B104.5 (2)
D—H···AD—HH···AD···AD—H···A
C1B—H1B···Cl4Aiii1.002.703.656 (4)160
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C1B—H1B⋯Cl4Ai1.002.703.656 (4)160

Symmetry code: (i) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  An empirical correction for absorption anisotropy.

Authors:  R H Blessing
Journal:  Acta Crystallogr A       Date:  1995-01-01       Impact factor: 2.290

3.  (1R,2R,5R,6R,9S,10S,13S,14S)-1,6,7,8,9,14,15,16,17,17-Decachloro-penta-cyclo-[12.2.1.1.0.0]octa-deca-7,15-diene.

Authors:  Nicole Riddell; Robert McCrindle; Gilles Arsenault; Alan J Lough
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-13
  3 in total

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