Literature DB >> 21202883

(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.

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

Abstract

The title compound, C(18)H(14)Cl(10), is a decachlorinated commercial flame retardant. The structure determination confirms the relative stereochemistry. The central eight-membered ring is in a chair-type conformation. In the crystal structure, there are no significant inter-molecular inter-actions and mol-ecules are separated by normal van der Waals distances.

Entities:  

Year:  2008        PMID： 21202883      PMCID： PMC2961698          DOI： 10.1107/S1600536808016231

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


Related literature

For related literature, see: Garcia et al. (1991 ▶); Hoh et al. (2006 ▶); Qiu et al. (2007 ▶); Sverko et al. (2008 ▶); Tomy et al. (2007 ▶).

Experimental

Crystal data

C18H14Cl10 M = 584.79 Orthorhombic, a = 11.4341 (2) Å b = 12.9704 (3) Å c = 15.0389 (4) Å V = 2230.34 (9) Å3 Z = 4 Mo Kα radiation μ = 1.25 mm−1 T = 150 (1) K 0.24 × 0.20 × 0.18 mm

Data collection

Bruker–Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.720, T max = 0.804 17031 measured reflections 5087 independent reflections 4585 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.072 S = 1.04 5087 reflections 253 parameters H-atom parameters constrained Δρmax = 0.34 e Å−3 Δρmin = −0.32 e Å−3 Absolute structure: Flack (1983 ▶), 2207 Friedel pairs Flack parameter: −0.01 (6) 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/S1600536808016231/bt2716sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016231/bt2716Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H14Cl10F000 = 1168
Mr = 584.79Dx = 1.742 Mg m−3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 17031 reflections
a = 11.4341 (2) Åθ = 2.7–27.5º
b = 12.9704 (3) ŵ = 1.26 mm−1
c = 15.0389 (4) ÅT = 150 (1) K
V = 2230.34 (9) Å3Block, colourless
Z = 40.24 × 0.20 × 0.18 mm
Bruker–Nonius KappaCCD diffractometer5087 independent reflections
Radiation source: fine-focus sealed tube4585 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.036
Detector resolution: 9 pixels mm-1θmax = 27.5º
T = 150(2) Kθmin = 2.7º
φ scans and ω scans with κ offsetsh = −14→14
Absorption correction: multi-scan(SORTAV; Blessing, 1995)k = −16→16
Tmin = 0.720, Tmax = 0.804l = −19→19
17031 measured reflections
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032  w = 1/[σ2(Fo2) + (0.03P)2 + 1.117P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.34 e Å−3
5087 reflectionsΔρmin = −0.32 e Å−3
253 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2207 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.01 (6)
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*/Ueq
Cl10.87131 (5)0.78434 (5)0.55246 (4)0.02288 (14)
Cl21.07256 (5)0.66212 (5)0.43725 (5)0.02523 (14)
Cl31.14507 (6)0.81013 (6)0.25760 (5)0.03027 (16)
Cl40.97237 (6)1.01756 (5)0.25571 (5)0.03129 (16)
Cl51.03310 (6)0.98603 (5)0.47707 (4)0.02853 (16)
Cl60.78892 (6)1.00833 (5)0.44082 (5)0.03032 (16)
Cl70.68597 (7)0.61445 (6)−0.03570 (5)0.03760 (18)
Cl80.45590 (8)0.74067 (6)0.04705 (6)0.0468 (2)
Cl90.36780 (6)0.61715 (7)0.23695 (6)0.0441 (2)
Cl100.53873 (7)0.41158 (6)0.26610 (5)0.0406 (2)
C10.7915 (2)0.78678 (19)0.37527 (16)0.0184 (5)
H1A0.71770.81610.40040.022*
C20.8244 (2)0.8505 (2)0.28950 (17)0.0195 (5)
H2A0.76140.90260.27900.023*
C30.8459 (2)0.7930 (2)0.20247 (17)0.0205 (5)
H3A0.89590.73250.21540.025*
H3B0.89070.83890.16240.025*
C40.7364 (2)0.75489 (19)0.15180 (17)0.0197 (5)
H4A0.66560.78170.18180.024*
H4B0.73780.78320.09070.024*
C50.7288 (2)0.63674 (19)0.14688 (17)0.0190 (5)
H5A0.80810.61030.13060.023*
C60.6879 (2)0.57719 (19)0.23264 (17)0.0192 (5)
H6A0.75060.52640.24790.023*
C70.6627 (2)0.6394 (2)0.31572 (17)0.0220 (6)
H7A0.61270.59820.35600.026*
H7B0.61880.70230.29910.026*
C80.7757 (2)0.6710 (2)0.36566 (17)0.0205 (5)
H8A0.77460.63960.42570.025*
H8B0.84400.64250.33350.025*
C90.8936 (2)0.81438 (18)0.43944 (18)0.0186 (5)
C101.0060 (2)0.77145 (19)0.40053 (17)0.0194 (5)
C111.0325 (2)0.8277 (2)0.32990 (17)0.0213 (5)
C120.9372 (2)0.9089 (2)0.32037 (17)0.0212 (5)
C130.9127 (2)0.93046 (19)0.42002 (18)0.0213 (6)
C140.6406 (2)0.5965 (2)0.07546 (17)0.0239 (6)
C150.5203 (2)0.6380 (2)0.09832 (19)0.0258 (6)
C160.4856 (2)0.5901 (2)0.17161 (19)0.0257 (6)
C170.5815 (2)0.5147 (2)0.19615 (19)0.0237 (6)
C180.6255 (3)0.4837 (2)0.10393 (18)0.0252 (6)
H18A0.56640.44620.06830.030*
H18B0.70000.44490.10560.030*
U11U22U33U12U13U23
Cl10.0260 (3)0.0273 (3)0.0153 (3)−0.0008 (3)0.0011 (3)0.0010 (3)
Cl20.0230 (3)0.0248 (3)0.0278 (4)0.0037 (3)−0.0027 (3)0.0018 (3)
Cl30.0259 (3)0.0390 (4)0.0259 (4)−0.0050 (3)0.0075 (3)−0.0007 (3)
Cl40.0420 (4)0.0240 (3)0.0279 (4)−0.0119 (3)−0.0062 (3)0.0095 (3)
Cl50.0351 (4)0.0252 (3)0.0253 (3)−0.0091 (3)−0.0081 (3)−0.0011 (3)
Cl60.0369 (4)0.0227 (3)0.0313 (4)0.0081 (3)−0.0059 (3)−0.0054 (3)
Cl70.0549 (5)0.0391 (4)0.0189 (3)−0.0113 (4)0.0010 (3)−0.0043 (3)
Cl80.0578 (5)0.0361 (4)0.0465 (5)0.0171 (4)−0.0290 (4)−0.0059 (4)
Cl90.0230 (3)0.0645 (5)0.0447 (5)−0.0044 (4)0.0035 (3)−0.0276 (4)
Cl100.0526 (5)0.0323 (4)0.0367 (4)−0.0228 (4)−0.0016 (4)0.0057 (3)
C10.0190 (12)0.0201 (12)0.0160 (13)−0.0019 (10)−0.0024 (10)0.0008 (10)
C20.0224 (12)0.0174 (12)0.0188 (13)0.0012 (10)−0.0026 (10)0.0015 (10)
C30.0218 (12)0.0225 (13)0.0172 (13)−0.0028 (11)−0.0007 (10)0.0013 (11)
C40.0257 (13)0.0186 (13)0.0150 (13)−0.0049 (10)−0.0029 (10)0.0019 (10)
C50.0192 (12)0.0185 (12)0.0193 (13)0.0009 (10)−0.0015 (10)−0.0029 (10)
C60.0196 (11)0.0190 (12)0.0190 (13)−0.0015 (10)−0.0026 (10)0.0016 (10)
C70.0190 (12)0.0259 (14)0.0210 (13)−0.0058 (11)−0.0003 (10)0.0021 (11)
C80.0223 (13)0.0207 (13)0.0186 (13)−0.0022 (11)−0.0013 (11)0.0016 (11)
C90.0220 (12)0.0174 (12)0.0163 (12)0.0005 (9)−0.0007 (10)0.0028 (10)
C100.0191 (12)0.0195 (12)0.0197 (13)−0.0007 (10)−0.0037 (10)−0.0010 (10)
C110.0195 (12)0.0233 (13)0.0210 (14)−0.0045 (11)0.0010 (11)−0.0051 (11)
C120.0276 (14)0.0182 (12)0.0179 (13)−0.0045 (11)−0.0028 (11)0.0036 (10)
C130.0235 (12)0.0185 (13)0.0220 (15)−0.0008 (11)−0.0020 (10)−0.0028 (10)
C140.0306 (14)0.0222 (13)0.0190 (14)0.0001 (12)−0.0026 (11)−0.0034 (11)
C150.0246 (13)0.0214 (13)0.0315 (16)0.0026 (11)−0.0145 (12)−0.0078 (11)
C160.0179 (12)0.0310 (15)0.0282 (16)−0.0047 (12)−0.0035 (11)−0.0109 (12)
C170.0262 (13)0.0181 (12)0.0267 (15)−0.0055 (11)0.0001 (11)−0.0004 (11)
C180.0299 (14)0.0196 (13)0.0261 (14)−0.0021 (12)−0.0017 (12)−0.0036 (11)
Cl1—C91.762 (3)C5—C141.563 (4)
Cl2—C101.701 (3)C5—C61.574 (3)
Cl3—C111.700 (3)C5—H5A1.0000
Cl4—C121.758 (3)C6—C71.515 (4)
Cl5—C131.775 (3)C6—C171.562 (3)
Cl6—C131.766 (3)C6—H6A1.0000
Cl7—C141.766 (3)C7—C81.550 (3)
Cl8—C151.706 (3)C7—H7A0.9900
Cl9—C161.704 (3)C7—H7B0.9900
Cl10—C171.771 (3)C8—H8A0.9900
C1—C81.519 (3)C8—H8B0.9900
C1—C91.557 (3)C9—C101.518 (3)
C1—C21.577 (3)C9—C131.549 (3)
C1—H1A1.0000C10—C111.324 (4)
C2—C31.526 (4)C11—C121.522 (4)
C2—C121.567 (4)C12—C131.550 (4)
C2—H2A1.0000C14—C151.517 (4)
C3—C41.547 (3)C14—C181.534 (4)
C3—H3A0.9900C15—C161.326 (4)
C3—H3B0.9900C16—C171.514 (4)
C4—C51.537 (3)C17—C181.529 (4)
C4—H4A0.9900C18—H18A0.9900
C4—H4B0.9900C18—H18B0.9900
C8—C1—C9112.1 (2)C10—C9—C1399.5 (2)
C8—C1—C2117.9 (2)C10—C9—C1108.2 (2)
C9—C1—C2102.00 (19)C13—C9—C1102.2 (2)
C8—C1—H1A108.1C10—C9—Cl1114.42 (17)
C9—C1—H1A108.1C13—C9—Cl1114.65 (18)
C2—C1—H1A108.1C1—C9—Cl1116.00 (18)
C3—C2—C12110.9 (2)C11—C10—C9107.5 (2)
C3—C2—C1118.9 (2)C11—C10—Cl2128.1 (2)
C12—C2—C1101.96 (19)C9—C10—Cl2124.01 (19)
C3—C2—H2A108.2C10—C11—C12107.0 (2)
C12—C2—H2A108.2C10—C11—Cl3127.8 (2)
C1—C2—H2A108.2C12—C11—Cl3125.06 (19)
C2—C3—C4116.6 (2)C11—C12—C1399.4 (2)
C2—C3—H3A108.1C11—C12—C2106.4 (2)
C4—C3—H3A108.1C13—C12—C2103.0 (2)
C2—C3—H3B108.1C11—C12—Cl4116.30 (19)
C4—C3—H3B108.1C13—C12—Cl4115.59 (18)
H3A—C3—H3B107.3C2—C12—Cl4114.32 (18)
C5—C4—C3112.9 (2)C9—C13—C1291.88 (19)
C5—C4—H4A109.0C9—C13—Cl6114.20 (18)
C3—C4—H4A109.0C12—C13—Cl6114.79 (18)
C5—C4—H4B109.0C9—C13—Cl5114.36 (18)
C3—C4—H4B109.0C12—C13—Cl5113.56 (18)
H4A—C4—H4B107.8Cl6—C13—Cl5107.68 (13)
C4—C5—C14113.8 (2)C15—C14—C18100.0 (2)
C4—C5—C6117.8 (2)C15—C14—C5108.1 (2)
C14—C5—C6101.98 (19)C18—C14—C5101.5 (2)
C4—C5—H5A107.6C15—C14—Cl7115.73 (19)
C14—C5—H5A107.6C18—C14—Cl7115.04 (18)
C6—C5—H5A107.6C5—C14—Cl7114.65 (19)
C7—C6—C17114.7 (2)C16—C15—C14107.1 (2)
C7—C6—C5118.1 (2)C16—C15—Cl8127.8 (2)
C17—C6—C5101.4 (2)C14—C15—Cl8124.5 (2)
C7—C6—H6A107.3C15—C16—C17106.8 (2)
C17—C6—H6A107.3C15—C16—Cl9128.3 (2)
C5—C6—H6A107.3C17—C16—Cl9124.4 (2)
C6—C7—C8112.5 (2)C16—C17—C18100.8 (2)
C6—C7—H7A109.1C16—C17—C6108.4 (2)
C8—C7—H7A109.1C18—C17—C6101.5 (2)
C6—C7—H7B109.1C16—C17—Cl10115.6 (2)
C8—C7—H7B109.1C18—C17—Cl10115.51 (19)
H7A—C7—H7B107.8C6—C17—Cl10113.47 (19)
C1—C8—C7114.0 (2)C17—C18—C1492.2 (2)
C1—C8—H8A108.8C17—C18—H18A113.2
C7—C8—H8A108.8C14—C18—H18A113.2
C1—C8—H8B108.8C17—C18—H18B113.2
C7—C8—H8B108.8C14—C18—H18B113.2
H8A—C8—H8B107.6H18A—C18—H18B110.6
  5 in total

1.  Dechlorane plus, a chlorinated flame retardant, in the Great Lakes.

Authors:  Eunha Hoh; Lingyan Zhu; Ronald A Hites
Journal:  Environ Sci Technol       Date:  2006-02-15       Impact factor: 9.028

2.  Dechlorane plus levels in sediment of the lower Great Lakes.

Authors:  Ed Sverko; Gregg T Tomy; Chris H Marvin; Donna Zaruk; Eric Reiner; Paul A Helm; Brad Hill; Brian E McCarry
Journal:  Environ Sci Technol       Date:  2008-01-15       Impact factor: 9.028

3.  A short history of SHELX.

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

4.  An empirical correction for absorption anisotropy.

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

5.  Isomers of dechlorane plus in Lake Winnipeg and Lake Ontario food webs.

Authors:  Gregg T Tomy; Kerri Pleskach; Nargis Ismail; D Michael Whittle; Paul A Helm; Ed Sverko; Donna Zaruk; Chris H Marvin
Journal:  Environ Sci Technol       Date:  2007-04-01       Impact factor: 9.028
  5 in total
  1 in total

1.  (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.

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

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