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1,2,3,4,5,6,7,8,13,13,14,14-Dodeca­chloro-1,4,4a,4b,5,8,8a,12b-octa­hydro-1,4:5,8-di­methano­tri­phenyl­ene at 90 K1

aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
*Correspondence e-mail: ffroncz@lsu.edu

(Received 13 July 2012; accepted 17 July 2012; online 25 July 2012)

The previously reported room-temperature crystal structure [Jaud Baldy, Negrel, Poite & Chanon (1993[Jaud, J., Baldy, A., Negrel, J. C., Poite, J. C. & Chanon, M. (1993). Z. Kristallogr. 204, 289-291.]). Z. Kristallogr. 204, 289–291] of the title compound, C20H8Cl12, is monoclinic with Z′ = 1, whereas the 90 K structure reported herein is triclinic with Z′ = 2 and shows a 2% volume contraction. The crystallographically independent unit chosen consists of both enanti­omers (Λ and Δ) of this propeller-like mol­ecule. Both enanti­omers display quasi-twofold symmetry, with average bond-length/bond-angle deviations of 0.0018 (4) Å and 0.41 (2)° for Λ, and 0.0026 (4) Å and 0.50 (2)° for Δ.

Related literature

For the structure of the room-temperature polymorph, see: Jaud et al. (1993[Jaud, J., Baldy, A., Negrel, J. C., Poite, J. C. & Chanon, M. (1993). Z. Kristallogr. 204, 289-291.]). For the preparation of the compound, see: Lacourcelle et al. (1993[Lacourcelle, C., Poite, J. C., Baldy, A., Jaud, J., Negrel, J. C. & Chanon, M. (1993). Acta Chem. Scand. 47, 92-94.]). For the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C20H8Cl12

  • Mr = 673.66

  • Triclinic, [P \overline 1]

  • a = 9.6434 (1) Å

  • b = 15.4287 (2) Å

  • c = 16.4161 (2) Å

  • α = 92.1948 (6)°

  • β = 98.2331 (7)°

  • γ = 91.3097 (6)°

  • V = 2414.53 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.39 mm−1

  • T = 90 K

  • 0.40 × 0.35 × 0.15 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[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.]) Tmin = 0.607, Tmax = 0.819

  • 111692 measured reflections

  • 30125 independent reflections

  • 24699 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.086

  • S = 1.03

  • 30125 reflections

  • 578 parameters

  • H-atom parameters constrained

  • Δρmax = 0.87 e Å−3

  • Δρmin = −0.63 e Å−3

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The crystal structure of the title compound at 298 K is monoclinic, P21/c, Z = 4, a = 9.743 (3), b = 15.523 (3), c = 16.575 (2) Å, β = 100.11 (2)°, in agreement with the published room-temperature structure (Jaud et al., 1993. CCDC refcode YASKOS, Allen, 2002). Upon cooling to 90 K, the material undergoes a phase change to triclinic (P1) and a volume contraction of 2%. The two crystallographically independent enantiomers chosen for the asymmetric unit are propeller-like with opposite pitch (Δ, Ia and Λ, Ib). Both display near twofold symmetry, with average off-symmetry bond-length/bond-angle deviations of 0.0018 (4) Å/0.41 (2)° (Ia) and 0.0026 (4) Å/0.50 (2)° (Ib). The bond lengths and bond angles are normal and are essentially as described by Jaud et al. (1993).

Related literature top

For the structure of the room-temperature polymorph, see: Jaud et al. (1993). For the preparation of the compound, see: Lacourcelle et al. (1993). For the Cambridge Structural Database, see: Allen (2002).

Experimental top

The compound was prepared by Lee Shui and Mark McLaughlin using the method described by Lacourcelle et al. (1993). A sample suitable for diffraction was recrystallized from ethyl acetate.

Refinement top

All H atoms were placed in calculated positions, guided by difference maps, with C—H bond distances 0.95 (aromatic C) and 1.00 (alkyl C) Å, Uiso = 1.2Ueq, and thereafter refined as riding.

Structure description top

The crystal structure of the title compound at 298 K is monoclinic, P21/c, Z = 4, a = 9.743 (3), b = 15.523 (3), c = 16.575 (2) Å, β = 100.11 (2)°, in agreement with the published room-temperature structure (Jaud et al., 1993. CCDC refcode YASKOS, Allen, 2002). Upon cooling to 90 K, the material undergoes a phase change to triclinic (P1) and a volume contraction of 2%. The two crystallographically independent enantiomers chosen for the asymmetric unit are propeller-like with opposite pitch (Δ, Ia and Λ, Ib). Both display near twofold symmetry, with average off-symmetry bond-length/bond-angle deviations of 0.0018 (4) Å/0.41 (2)° (Ia) and 0.0026 (4) Å/0.50 (2)° (Ib). The bond lengths and bond angles are normal and are essentially as described by Jaud et al. (1993).

For the structure of the room-temperature polymorph, see: Jaud et al. (1993). For the preparation of the compound, see: Lacourcelle et al. (1993). For the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of Ia (Δ, 50% probability displacement ellipsoids)
[Figure 2] Fig. 2. View of Ib (Λ, 50% probability displacement ellipsoids)
1,2,3,4,5,6,7,8,13,13,14,14-Dodecachloro-1,4,4a,4b,5,8,8a,12b- octahydro-1,4:5,8-dimethanotriphenylene top
Crystal data top
C20H8Cl12Z = 4
Mr = 673.66F(000) = 1328
Triclinic, P1Dx = 1.853 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6434 (1) ÅCell parameters from 27797 reflections
b = 15.4287 (2) Åθ = 2.6–40.3°
c = 16.4161 (2) ŵ = 1.39 mm1
α = 92.1948 (6)°T = 90 K
β = 98.2331 (7)°Prism, colourless
γ = 91.3097 (6)°0.40 × 0.35 × 0.15 mm
V = 2414.53 (5) Å3
Data collection top
Nonius KappaCCD
diffractometer
30125 independent reflections
Radiation source: sealed tube24699 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromatorRint = 0.026
Detector resolution: 9 pixels mm-1θmax = 40.3°, θmin = 2.6°
CCD rotation images, thick slices scansh = 1717
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 2828
Tmin = 0.607, Tmax = 0.819l = 2929
111692 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0362P)2 + 1.2577P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
30125 reflectionsΔρmax = 0.87 e Å3
578 parametersΔρmin = 0.63 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0013 (2)
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H8Cl12γ = 91.3097 (6)°
Mr = 673.66V = 2414.53 (5) Å3
Triclinic, P1Z = 4
a = 9.6434 (1) ÅMo Kα radiation
b = 15.4287 (2) ŵ = 1.39 mm1
c = 16.4161 (2) ÅT = 90 K
α = 92.1948 (6)°0.40 × 0.35 × 0.15 mm
β = 98.2331 (7)°
Data collection top
Nonius KappaCCD
diffractometer
30125 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
24699 reflections with I > 2σ(I)
Tmin = 0.607, Tmax = 0.819Rint = 0.026
111692 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.03Δρmax = 0.87 e Å3
30125 reflectionsΔρmin = 0.63 e Å3
578 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.78302 (10)0.24744 (6)0.36584 (6)0.01060 (13)
H10.7180.27850.39840.013*
C20.76826 (10)0.15090 (6)0.37568 (6)0.01118 (14)
C30.77164 (12)0.12163 (7)0.45581 (6)0.01484 (16)
H30.76460.16220.49990.018*
C40.78510 (13)0.03398 (7)0.47153 (7)0.01839 (18)
H40.78530.01480.52580.022*
C50.79834 (13)0.02536 (7)0.40736 (7)0.01770 (18)
H50.81490.08450.41830.021*
C60.78719 (12)0.00244 (7)0.32715 (7)0.01483 (16)
H60.79380.03860.28330.018*
C70.76641 (10)0.08995 (6)0.30980 (6)0.01141 (14)
C80.72700 (10)0.11372 (6)0.22086 (6)0.01102 (13)
H80.79570.08930.18660.013*
C90.70962 (10)0.21274 (6)0.20593 (6)0.01055 (13)
H90.75870.22640.15810.013*
C100.76252 (10)0.27912 (6)0.27577 (6)0.01032 (13)
H100.69520.32760.2730.012*
C110.91010 (10)0.31842 (6)0.26664 (6)0.01082 (13)
C120.95297 (10)0.36467 (6)0.35265 (6)0.01182 (14)
C130.94026 (10)0.27907 (6)0.39788 (6)0.01102 (13)
C141.03221 (10)0.22190 (6)0.35207 (6)0.01196 (14)
C151.01323 (10)0.24454 (7)0.27332 (6)0.01183 (14)
C160.54883 (10)0.21886 (6)0.17658 (6)0.01145 (14)
C170.52148 (10)0.13722 (6)0.11775 (6)0.01270 (14)
C180.57301 (10)0.07562 (6)0.18742 (6)0.01136 (14)
C190.48189 (10)0.10455 (6)0.25116 (6)0.01187 (14)
C200.47091 (10)0.19063 (6)0.24619 (6)0.01197 (14)
Cl10.83666 (3)0.444688 (16)0.378408 (16)0.01515 (4)
Cl21.12467 (3)0.411451 (17)0.367166 (16)0.01537 (4)
Cl30.98690 (3)0.288372 (18)0.504965 (14)0.01546 (4)
Cl41.12522 (3)0.138821 (18)0.394002 (17)0.01819 (5)
Cl51.07638 (3)0.195595 (19)0.192404 (16)0.01775 (4)
Cl60.91267 (3)0.383648 (17)0.181692 (15)0.01553 (4)
Cl70.62374 (3)0.132935 (18)0.036646 (15)0.01693 (4)
Cl80.34348 (3)0.119848 (18)0.074104 (16)0.01669 (4)
Cl90.56086 (3)0.034447 (16)0.156692 (16)0.01555 (4)
Cl100.42601 (3)0.039085 (17)0.321116 (17)0.01683 (4)
Cl110.40182 (3)0.259640 (17)0.311679 (18)0.01724 (4)
Cl120.49903 (3)0.317864 (16)0.134127 (17)0.01638 (4)
C210.70185 (10)0.39226 (6)0.72349 (6)0.01099 (13)
H210.77640.42240.69770.013*
C220.72147 (10)0.41473 (6)0.81506 (6)0.01236 (14)
C230.73181 (12)0.50254 (7)0.84174 (7)0.01735 (18)
H230.74410.54570.80350.021*
C240.72439 (14)0.52707 (8)0.92324 (8)0.0220 (2)
H240.73470.58650.94080.026*
C250.70191 (15)0.46452 (9)0.97910 (7)0.0227 (2)
H250.68830.48141.03360.027*
C260.69956 (13)0.37723 (8)0.95468 (7)0.01833 (18)
H260.68720.33440.99330.022*
C270.71524 (11)0.35144 (7)0.87372 (6)0.01303 (15)
C280.74356 (10)0.25743 (6)0.85610 (6)0.01152 (14)
H280.67810.21970.88220.014*
C290.73930 (10)0.22747 (6)0.76363 (6)0.01075 (13)
H290.67540.17510.75230.013*
C300.69489 (10)0.29315 (6)0.69746 (6)0.01106 (13)
H300.75660.28510.65390.013*
C310.54023 (10)0.27880 (6)0.65463 (6)0.01190 (14)
C320.52032 (10)0.36220 (6)0.60443 (6)0.01211 (14)
C330.55125 (10)0.42229 (6)0.68299 (6)0.01044 (13)
C340.44750 (10)0.38391 (6)0.73405 (6)0.01182 (14)
C350.44278 (10)0.29802 (6)0.71796 (6)0.01284 (15)
C360.89301 (10)0.19842 (6)0.75984 (6)0.01145 (14)
C370.92908 (10)0.15480 (6)0.84375 (6)0.01255 (14)
C380.90153 (10)0.23844 (6)0.89310 (6)0.01190 (14)
C390.99247 (10)0.30344 (7)0.85577 (6)0.01231 (14)
C400.98700 (10)0.27995 (7)0.77598 (6)0.01191 (14)
Cl130.64205 (3)0.377793 (19)0.534965 (15)0.01720 (4)
Cl140.34960 (3)0.370694 (18)0.549642 (16)0.01676 (4)
Cl150.53663 (3)0.532852 (15)0.665173 (16)0.01426 (4)
Cl160.37045 (3)0.441131 (18)0.804244 (17)0.01757 (4)
Cl170.35863 (3)0.221032 (19)0.76498 (2)0.02185 (5)
Cl180.50770 (3)0.180207 (17)0.597606 (18)0.01900 (5)
Cl190.81665 (3)0.066381 (16)0.857572 (17)0.01663 (4)
Cl201.10430 (3)0.120062 (18)0.864312 (16)0.01591 (4)
Cl210.93820 (3)0.232330 (19)1.000170 (15)0.01646 (4)
Cl221.06791 (3)0.393670 (18)0.906893 (16)0.01752 (4)
Cl231.05143 (3)0.336268 (18)0.701995 (15)0.01620 (4)
Cl240.91419 (3)0.134541 (17)0.672205 (15)0.01600 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0102 (3)0.0109 (3)0.0109 (3)0.0006 (3)0.0022 (3)0.0009 (2)
C20.0118 (3)0.0111 (3)0.0109 (3)0.0004 (3)0.0023 (3)0.0009 (3)
C30.0197 (4)0.0137 (4)0.0116 (3)0.0007 (3)0.0036 (3)0.0020 (3)
C40.0258 (5)0.0151 (4)0.0146 (4)0.0001 (4)0.0030 (4)0.0048 (3)
C50.0224 (5)0.0122 (4)0.0182 (4)0.0020 (3)0.0009 (4)0.0033 (3)
C60.0169 (4)0.0117 (3)0.0154 (4)0.0024 (3)0.0005 (3)0.0007 (3)
C70.0113 (3)0.0111 (3)0.0118 (3)0.0014 (3)0.0014 (3)0.0011 (3)
C80.0102 (3)0.0114 (3)0.0113 (3)0.0008 (3)0.0013 (3)0.0006 (3)
C90.0093 (3)0.0116 (3)0.0107 (3)0.0004 (3)0.0010 (3)0.0012 (3)
C100.0092 (3)0.0109 (3)0.0107 (3)0.0001 (2)0.0012 (3)0.0010 (2)
C110.0097 (3)0.0124 (3)0.0102 (3)0.0006 (3)0.0010 (3)0.0018 (3)
C120.0107 (3)0.0124 (3)0.0120 (3)0.0009 (3)0.0008 (3)0.0006 (3)
C130.0104 (3)0.0132 (3)0.0094 (3)0.0001 (3)0.0011 (3)0.0009 (3)
C140.0100 (3)0.0144 (4)0.0118 (3)0.0023 (3)0.0017 (3)0.0026 (3)
C150.0098 (3)0.0157 (4)0.0103 (3)0.0012 (3)0.0023 (3)0.0009 (3)
C160.0106 (3)0.0108 (3)0.0125 (3)0.0003 (3)0.0001 (3)0.0011 (3)
C170.0118 (4)0.0140 (4)0.0117 (3)0.0009 (3)0.0003 (3)0.0002 (3)
C180.0111 (3)0.0106 (3)0.0123 (3)0.0000 (3)0.0016 (3)0.0009 (3)
C190.0106 (3)0.0115 (3)0.0139 (4)0.0002 (3)0.0031 (3)0.0004 (3)
C200.0099 (3)0.0114 (3)0.0147 (4)0.0009 (3)0.0023 (3)0.0003 (3)
Cl10.01452 (9)0.01185 (8)0.01893 (10)0.00055 (7)0.00233 (8)0.00109 (7)
Cl20.01118 (9)0.01763 (10)0.01655 (9)0.00436 (7)0.00006 (7)0.00173 (7)
Cl30.01539 (10)0.02149 (10)0.00901 (8)0.00196 (8)0.00049 (7)0.00051 (7)
Cl40.01609 (10)0.02054 (11)0.01883 (10)0.00766 (8)0.00282 (8)0.00687 (8)
Cl50.01531 (10)0.02630 (12)0.01232 (9)0.00480 (8)0.00425 (7)0.00134 (8)
Cl60.01548 (10)0.01764 (10)0.01337 (9)0.00241 (7)0.00075 (7)0.00634 (7)
Cl70.01755 (10)0.02238 (11)0.01071 (9)0.00275 (8)0.00244 (7)0.00091 (7)
Cl80.01222 (9)0.01876 (10)0.01734 (10)0.00185 (7)0.00323 (7)0.00030 (8)
Cl90.01529 (10)0.01106 (8)0.01946 (10)0.00016 (7)0.00067 (8)0.00321 (7)
Cl100.01749 (10)0.01530 (9)0.01925 (10)0.00123 (8)0.00744 (8)0.00352 (8)
Cl110.01515 (10)0.01373 (9)0.02399 (11)0.00053 (7)0.00797 (8)0.00388 (8)
Cl120.01552 (10)0.01303 (9)0.01943 (10)0.00099 (7)0.00262 (8)0.00466 (7)
C210.0096 (3)0.0118 (3)0.0114 (3)0.0004 (3)0.0008 (3)0.0013 (3)
C220.0120 (4)0.0123 (3)0.0120 (3)0.0003 (3)0.0007 (3)0.0008 (3)
C230.0193 (4)0.0132 (4)0.0171 (4)0.0014 (3)0.0051 (3)0.0015 (3)
C240.0272 (6)0.0168 (4)0.0187 (5)0.0065 (4)0.0075 (4)0.0061 (3)
C250.0280 (6)0.0235 (5)0.0151 (4)0.0084 (4)0.0015 (4)0.0061 (4)
C260.0215 (5)0.0212 (5)0.0122 (4)0.0045 (4)0.0021 (3)0.0012 (3)
C270.0133 (4)0.0143 (4)0.0112 (3)0.0016 (3)0.0010 (3)0.0004 (3)
C280.0106 (3)0.0135 (3)0.0109 (3)0.0004 (3)0.0023 (3)0.0022 (3)
C290.0093 (3)0.0118 (3)0.0110 (3)0.0011 (3)0.0008 (3)0.0008 (3)
C300.0099 (3)0.0120 (3)0.0110 (3)0.0008 (3)0.0007 (3)0.0001 (3)
C310.0107 (3)0.0109 (3)0.0132 (3)0.0005 (3)0.0010 (3)0.0005 (3)
C320.0116 (3)0.0140 (3)0.0103 (3)0.0013 (3)0.0001 (3)0.0006 (3)
C330.0093 (3)0.0107 (3)0.0114 (3)0.0002 (2)0.0014 (3)0.0012 (3)
C340.0098 (3)0.0135 (3)0.0124 (3)0.0001 (3)0.0025 (3)0.0012 (3)
C350.0098 (3)0.0123 (3)0.0167 (4)0.0009 (3)0.0023 (3)0.0032 (3)
C360.0101 (3)0.0137 (3)0.0102 (3)0.0017 (3)0.0005 (3)0.0002 (3)
C370.0104 (3)0.0143 (4)0.0129 (3)0.0014 (3)0.0010 (3)0.0028 (3)
C380.0113 (3)0.0152 (4)0.0092 (3)0.0000 (3)0.0013 (3)0.0021 (3)
C390.0108 (3)0.0152 (4)0.0106 (3)0.0017 (3)0.0008 (3)0.0013 (3)
C400.0103 (3)0.0160 (4)0.0096 (3)0.0006 (3)0.0015 (3)0.0023 (3)
Cl130.01770 (10)0.02354 (11)0.01141 (9)0.00470 (8)0.00434 (7)0.00335 (8)
Cl140.01352 (9)0.01905 (10)0.01587 (10)0.00283 (8)0.00431 (7)0.00008 (8)
Cl150.01306 (9)0.01089 (8)0.01855 (10)0.00068 (7)0.00050 (7)0.00358 (7)
Cl160.01555 (10)0.02152 (11)0.01677 (10)0.00244 (8)0.00659 (8)0.00163 (8)
Cl170.01655 (11)0.01744 (11)0.03321 (14)0.00172 (8)0.00695 (10)0.01084 (10)
Cl180.01851 (11)0.01363 (9)0.02210 (11)0.00153 (8)0.00507 (9)0.00519 (8)
Cl190.01466 (10)0.01355 (9)0.02162 (11)0.00028 (7)0.00144 (8)0.00481 (8)
Cl200.01137 (9)0.02036 (10)0.01609 (9)0.00441 (7)0.00072 (7)0.00441 (8)
Cl210.01617 (10)0.02432 (11)0.00905 (8)0.00128 (8)0.00142 (7)0.00381 (7)
Cl220.01692 (10)0.01942 (10)0.01496 (9)0.00570 (8)0.00048 (8)0.00125 (8)
Cl230.01377 (9)0.02338 (11)0.01183 (9)0.00289 (8)0.00262 (7)0.00475 (8)
Cl240.01656 (10)0.01830 (10)0.01279 (9)0.00548 (8)0.00096 (7)0.00253 (7)
Geometric parameters (Å, º) top
C1—C21.5099 (13)C21—C221.5136 (14)
C1—C101.5623 (13)C21—C301.5694 (13)
C1—C131.5913 (13)C21—C331.5949 (13)
C1—H11C21—H211
C2—C31.4033 (14)C22—C271.4037 (14)
C2—C71.4036 (14)C22—C231.4046 (14)
C3—C41.3919 (15)C23—C241.3885 (17)
C3—H30.95C23—H230.95
C4—C51.3908 (17)C24—C251.391 (2)
C4—H40.95C24—H240.95
C5—C61.3907 (15)C25—C261.3891 (17)
C5—H50.95C25—H250.95
C6—C71.4035 (14)C26—C271.4026 (15)
C6—H60.95C26—H260.95
C7—C81.5163 (13)C27—C281.5070 (14)
C8—C91.5655 (13)C28—C291.5643 (13)
C8—C181.5980 (13)C28—C381.5951 (14)
C8—H81C28—H281
C9—C101.5305 (13)C29—C301.5366 (13)
C9—C161.5625 (13)C29—C361.5673 (13)
C9—H91C29—H291
C10—C111.5633 (13)C30—C311.5622 (13)
C10—H101C30—H301
C11—C151.5265 (14)C31—C351.5233 (15)
C11—C121.5543 (13)C31—C321.5554 (14)
C11—Cl61.7535 (10)C31—Cl181.7531 (10)
C12—C131.5506 (14)C32—C331.5484 (13)
C12—Cl11.7664 (10)C32—Cl131.7685 (10)
C12—Cl21.7716 (10)C32—Cl141.7695 (10)
C13—C141.5185 (14)C33—C341.5183 (13)
C13—Cl31.7505 (9)C33—Cl151.7472 (9)
C14—C151.3403 (13)C34—C351.3398 (14)
C14—Cl41.6926 (10)C34—Cl161.6902 (10)
C15—Cl51.6976 (10)C35—Cl171.6943 (10)
C16—C201.5262 (14)C36—C401.5256 (14)
C16—C171.5517 (14)C36—C371.5544 (13)
C16—Cl121.7518 (10)C36—Cl241.7514 (10)
C17—C181.5493 (14)C37—C381.5459 (14)
C17—Cl71.7668 (11)C37—Cl191.7648 (10)
C17—Cl81.7730 (10)C37—Cl201.7744 (10)
C18—C191.5204 (14)C38—C391.5202 (14)
C18—Cl91.7495 (10)C38—Cl211.7492 (10)
C19—C201.3395 (14)C39—C401.3390 (14)
C19—Cl101.6943 (10)C39—Cl221.6915 (10)
C20—Cl111.6980 (10)C40—Cl231.6995 (10)
C2—C1—C10116.62 (8)C22—C21—C30116.46 (8)
C2—C1—C13109.50 (8)C22—C21—C33109.13 (8)
C10—C1—C13101.60 (7)C30—C21—C33101.61 (7)
C2—C1—H1109.6C22—C21—H21109.8
C10—C1—H1109.6C30—C21—H21109.8
C13—C1—H1109.6C33—C21—H21109.8
C3—C2—C7119.20 (9)C27—C22—C23118.69 (9)
C3—C2—C1117.67 (8)C27—C22—C21122.21 (9)
C7—C2—C1122.78 (8)C23—C22—C21118.77 (9)
C4—C3—C2120.93 (10)C24—C23—C22120.94 (11)
C4—C3—H3119.5C24—C23—H23119.5
C2—C3—H3119.5C22—C23—H23119.5
C5—C4—C3119.68 (10)C23—C24—C25119.96 (11)
C5—C4—H4120.2C23—C24—H24120
C3—C4—H4120.2C25—C24—H24120
C6—C5—C4119.63 (10)C26—C25—C24119.55 (11)
C6—C5—H5120.2C26—C25—H25120.2
C4—C5—H5120.2C24—C25—H25120.2
C5—C6—C7121.21 (10)C25—C26—C27120.86 (11)
C5—C6—H6119.4C25—C26—H26119.6
C7—C6—H6119.4C27—C26—H26119.6
C6—C7—C2118.77 (9)C26—C27—C22119.35 (10)
C6—C7—C8118.72 (9)C26—C27—C28117.94 (9)
C2—C7—C8122.16 (8)C22—C27—C28122.23 (9)
C7—C8—C9115.90 (8)C27—C28—C29116.94 (8)
C7—C8—C18109.08 (8)C27—C28—C38109.12 (8)
C9—C8—C18101.61 (7)C29—C28—C38101.68 (7)
C7—C8—H8110C27—C28—H28109.6
C9—C8—H8110C29—C28—H28109.6
C18—C8—H8110C38—C28—H28109.6
C10—C9—C16112.28 (8)C30—C29—C28118.17 (8)
C10—C9—C8119.29 (8)C30—C29—C36110.65 (8)
C16—C9—C8102.75 (7)C28—C29—C36102.98 (7)
C10—C9—H9107.3C30—C29—H29108.2
C16—C9—H9107.3C28—C29—H29108.2
C8—C9—H9107.3C36—C29—H29108.2
C9—C10—C1117.92 (8)C29—C30—C31113.40 (8)
C9—C10—C11111.87 (8)C29—C30—C21118.58 (8)
C1—C10—C11103.20 (7)C31—C30—C21102.81 (7)
C9—C10—H10107.8C29—C30—H30107.1
C1—C10—H10107.8C31—C30—H30107.1
C11—C10—H10107.8C21—C30—H30107.1
C15—C11—C1299.75 (7)C35—C31—C3299.48 (8)
C15—C11—C10107.59 (8)C35—C31—C30108.49 (8)
C12—C11—C10101.23 (7)C32—C31—C30100.82 (7)
C15—C11—Cl6115.79 (7)C35—C31—Cl18115.94 (7)
C12—C11—Cl6115.87 (7)C32—C31—Cl18115.82 (7)
C10—C11—Cl6114.67 (6)C30—C31—Cl18114.34 (7)
C13—C12—C1192.42 (7)C33—C32—C3192.48 (7)
C13—C12—Cl1113.60 (7)C33—C32—Cl13112.85 (7)
C11—C12—Cl1114.64 (7)C31—C32—Cl13114.98 (7)
C13—C12—Cl2113.77 (7)C33—C32—Cl14114.30 (7)
C11—C12—Cl2113.72 (7)C31—C32—Cl14113.66 (7)
Cl1—C12—Cl2108.22 (5)Cl13—C32—Cl14108.13 (5)
C14—C13—C1299.82 (8)C34—C33—C3299.98 (7)
C14—C13—C1106.03 (7)C34—C33—C21105.85 (7)
C12—C13—C1102.45 (7)C32—C33—C21102.54 (7)
C14—C13—Cl3115.75 (7)C34—C33—Cl15116.02 (7)
C12—C13—Cl3114.89 (7)C32—C33—Cl15114.41 (7)
C1—C13—Cl3115.87 (7)C21—C33—Cl15116.01 (6)
C15—C14—C13107.20 (8)C35—C34—C33106.63 (8)
C15—C14—Cl4128.20 (8)C35—C34—Cl16128.68 (8)
C13—C14—Cl4124.28 (7)C33—C34—Cl16124.37 (7)
C14—C15—C11107.22 (8)C34—C35—C31107.86 (8)
C14—C15—Cl5127.72 (8)C34—C35—Cl17127.52 (8)
C11—C15—Cl5124.79 (7)C31—C35—Cl17124.34 (7)
C20—C16—C1799.79 (8)C40—C36—C37100.05 (7)
C20—C16—C9108.31 (8)C40—C36—C29106.76 (8)
C17—C16—C9100.91 (8)C37—C36—C29101.62 (8)
C20—C16—Cl12115.58 (7)C40—C36—Cl24115.80 (7)
C17—C16—Cl12116.17 (7)C37—C36—Cl24115.92 (7)
C9—C16—Cl12114.22 (7)C29—C36—Cl24114.76 (6)
C18—C17—C1692.43 (7)C38—C37—C3692.52 (7)
C18—C17—Cl7112.78 (7)C38—C37—Cl19113.76 (7)
C16—C17—Cl7114.95 (7)C36—C37—Cl19114.29 (7)
C18—C17—Cl8114.39 (7)C38—C37—Cl20113.72 (7)
C16—C17—Cl8114.08 (7)C36—C37—Cl20114.20 (7)
Cl7—C17—Cl8107.83 (5)Cl19—C37—Cl20107.95 (5)
C19—C18—C1799.77 (8)C39—C38—C37100.27 (8)
C19—C18—C8105.71 (7)C39—C38—C28105.99 (8)
C17—C18—C8102.71 (7)C37—C38—C28101.98 (7)
C19—C18—Cl9116.46 (7)C39—C38—Cl21115.08 (7)
C17—C18—Cl9114.10 (7)C37—C38—Cl21114.92 (7)
C8—C18—Cl9116.01 (7)C28—C38—Cl21116.56 (7)
C20—C19—C18106.61 (8)C40—C39—C38107.24 (8)
C20—C19—Cl10128.56 (8)C40—C39—Cl22128.51 (8)
C18—C19—Cl10124.41 (7)C38—C39—Cl22123.90 (7)
C19—C20—C16107.69 (8)C39—C40—C36107.17 (8)
C19—C20—Cl11127.26 (8)C39—C40—Cl23127.44 (8)
C16—C20—Cl11124.64 (7)C36—C40—Cl23124.86 (7)
C10—C1—C2—C3173.50 (9)C30—C21—C22—C278.24 (14)
C13—C1—C2—C371.92 (11)C33—C21—C22—C27106.00 (10)
C10—C1—C2—C713.41 (13)C30—C21—C22—C23178.47 (9)
C13—C1—C2—C7101.18 (10)C33—C21—C22—C2367.29 (12)
C7—C2—C3—C45.48 (16)C27—C22—C23—C245.27 (16)
C1—C2—C3—C4167.88 (10)C21—C22—C23—C24168.26 (10)
C2—C3—C4—C51.35 (18)C22—C23—C24—C252.09 (19)
C3—C4—C5—C64.92 (18)C23—C24—C25—C265.7 (2)
C4—C5—C6—C71.69 (18)C24—C25—C26—C271.98 (19)
C5—C6—C7—C25.11 (16)C25—C26—C27—C225.41 (17)
C5—C6—C7—C8168.25 (10)C25—C26—C27—C28166.77 (11)
C3—C2—C7—C68.57 (15)C23—C22—C27—C268.92 (15)
C1—C2—C7—C6164.42 (9)C21—C22—C27—C26164.38 (10)
C3—C2—C7—C8164.54 (9)C23—C22—C27—C28162.92 (10)
C1—C2—C7—C822.46 (15)C21—C22—C27—C2823.78 (15)
C6—C7—C8—C9178.35 (9)C26—C27—C28—C29171.49 (9)
C2—C7—C8—C98.53 (13)C22—C27—C28—C2916.56 (14)
C6—C7—C8—C1867.77 (11)C26—C27—C28—C3873.90 (12)
C2—C7—C8—C18105.35 (10)C22—C27—C28—C3898.05 (11)
C7—C8—C9—C1013.07 (12)C27—C28—C29—C305.02 (12)
C18—C8—C9—C10131.16 (8)C38—C28—C29—C30123.72 (9)
C7—C8—C9—C16111.87 (9)C27—C28—C29—C36117.26 (9)
C18—C8—C9—C166.21 (9)C38—C28—C29—C361.44 (9)
C16—C9—C10—C199.28 (9)C28—C29—C30—C31101.76 (10)
C8—C9—C10—C120.94 (12)C36—C29—C30—C31139.94 (8)
C16—C9—C10—C11141.30 (8)C28—C29—C30—C2118.97 (12)
C8—C9—C10—C1198.47 (10)C36—C29—C30—C2199.33 (10)
C2—C1—C10—C98.32 (12)C22—C21—C30—C2912.98 (12)
C13—C1—C10—C9127.27 (8)C33—C21—C30—C29131.41 (8)
C2—C1—C10—C11115.55 (9)C22—C21—C30—C31113.02 (9)
C13—C1—C10—C113.40 (9)C33—C21—C30—C315.41 (9)
C9—C10—C11—C1563.17 (9)C29—C30—C31—C3566.67 (10)
C1—C10—C11—C1564.59 (9)C21—C30—C31—C3562.61 (9)
C9—C10—C11—C12167.29 (7)C29—C30—C31—C32170.59 (8)
C1—C10—C11—C1239.54 (9)C21—C30—C31—C3241.31 (9)
C9—C10—C11—Cl667.21 (9)C29—C30—C31—Cl1864.44 (10)
C1—C10—C11—Cl6165.03 (6)C21—C30—C31—Cl18166.28 (7)
C15—C11—C12—C1351.76 (8)C35—C31—C32—C3351.48 (8)
C10—C11—C12—C1358.53 (8)C30—C31—C32—C3359.58 (8)
Cl6—C11—C12—C13176.78 (7)Cl18—C31—C32—C33176.46 (7)
C15—C11—C12—Cl1169.16 (6)C35—C31—C32—Cl13168.16 (6)
C10—C11—C12—Cl158.87 (8)C30—C31—C32—Cl1357.11 (9)
Cl6—C11—C12—Cl165.82 (9)Cl18—C31—C32—Cl1366.86 (9)
C15—C11—C12—Cl265.58 (8)C35—C31—C32—Cl1466.47 (8)
C10—C11—C12—Cl2175.87 (6)C30—C31—C32—Cl14177.53 (6)
Cl6—C11—C12—Cl259.44 (9)Cl18—C31—C32—Cl1458.51 (9)
C11—C12—C13—C1452.50 (8)C31—C32—C33—C3452.74 (8)
Cl1—C12—C13—C14170.78 (6)Cl13—C32—C33—C34171.23 (6)
Cl2—C12—C13—C1464.80 (8)Cl14—C32—C33—C3464.66 (8)
C11—C12—C13—C156.48 (8)C31—C32—C33—C2156.12 (8)
Cl1—C12—C13—C161.80 (8)Cl13—C32—C33—C2162.37 (8)
Cl2—C12—C13—C1173.78 (6)Cl14—C32—C33—C21173.52 (6)
C11—C12—C13—Cl3177.01 (7)C31—C32—C33—Cl15177.42 (6)
Cl1—C12—C13—Cl364.72 (8)Cl13—C32—C33—Cl1564.09 (8)
Cl2—C12—C13—Cl359.71 (9)Cl14—C32—C33—Cl1560.01 (9)
C2—C1—C13—C1453.64 (9)C22—C21—C33—C3451.60 (10)
C10—C1—C13—C1470.27 (8)C30—C21—C33—C3471.95 (9)
C2—C1—C13—C12157.83 (8)C22—C21—C33—C32155.94 (8)
C10—C1—C13—C1233.93 (9)C30—C21—C33—C3232.39 (9)
C2—C1—C13—Cl376.28 (9)C22—C21—C33—Cl1578.63 (9)
C10—C1—C13—Cl3159.81 (6)C30—C21—C33—Cl15157.82 (7)
C12—C13—C14—C1535.79 (10)C32—C33—C34—C3536.13 (10)
C1—C13—C14—C1570.31 (10)C21—C33—C34—C3570.08 (10)
Cl3—C13—C14—C15159.70 (7)Cl15—C33—C34—C35159.69 (7)
C12—C13—C14—Cl4150.16 (8)C32—C33—C34—Cl16149.88 (7)
C1—C13—C14—Cl4103.74 (9)C21—C33—C34—Cl16103.91 (9)
Cl3—C13—C14—Cl426.25 (11)Cl15—C33—C34—Cl1626.32 (11)
C13—C14—C15—C111.03 (11)C33—C34—C35—C311.40 (11)
Cl4—C14—C15—C11174.77 (8)Cl16—C34—C35—C31175.04 (8)
C13—C14—C15—Cl5173.21 (8)C33—C34—C35—Cl17172.77 (8)
Cl4—C14—C15—Cl50.53 (15)Cl16—C34—C35—Cl170.88 (15)
C12—C11—C15—C1433.98 (10)C32—C31—C35—C3433.58 (10)
C10—C11—C15—C1471.19 (10)C30—C31—C35—C3471.28 (10)
Cl6—C11—C15—C14159.06 (7)Cl18—C31—C35—C34158.48 (7)
C12—C11—C15—Cl5151.57 (8)C32—C31—C35—Cl17152.03 (7)
C10—C11—C15—Cl5103.26 (9)C30—C31—C35—Cl17103.11 (9)
Cl6—C11—C15—Cl526.49 (11)Cl18—C31—C35—Cl1727.12 (11)
C10—C9—C16—C2067.18 (10)C30—C29—C36—C4060.71 (9)
C8—C9—C16—C2062.24 (9)C28—C29—C36—C4066.49 (9)
C10—C9—C16—C17171.43 (8)C30—C29—C36—C37165.07 (8)
C8—C9—C16—C1742.02 (9)C28—C29—C36—C3737.87 (9)
C10—C9—C16—Cl1263.17 (9)C30—C29—C36—Cl2469.04 (9)
C8—C9—C16—Cl12167.41 (6)C28—C29—C36—Cl24163.76 (6)
C20—C16—C17—C1851.30 (8)C40—C36—C37—C3851.35 (8)
C9—C16—C17—C1859.68 (8)C29—C36—C37—C3858.25 (8)
Cl12—C16—C17—C18176.26 (7)Cl24—C36—C37—C38176.64 (7)
C20—C16—C17—Cl7167.86 (7)C40—C36—C37—Cl19168.89 (7)
C9—C16—C17—Cl756.89 (9)C29—C36—C37—Cl1959.29 (9)
Cl12—C16—C17—Cl767.18 (9)Cl24—C36—C37—Cl1965.83 (9)
C20—C16—C17—Cl866.84 (8)C40—C36—C37—Cl2066.11 (9)
C9—C16—C17—Cl8177.82 (6)C29—C36—C37—Cl20175.71 (6)
Cl12—C16—C17—Cl858.12 (9)Cl24—C36—C37—Cl2059.17 (9)
C16—C17—C18—C1953.07 (8)C36—C37—C38—C3951.74 (8)
Cl7—C17—C18—C19171.48 (6)Cl19—C37—C38—C39169.73 (6)
Cl8—C17—C18—C1964.80 (8)Cl20—C37—C38—C3966.13 (8)
C16—C17—C18—C855.62 (8)C36—C37—C38—C2857.20 (8)
Cl7—C17—C18—C862.79 (8)Cl19—C37—C38—C2860.78 (8)
Cl8—C17—C18—C8173.50 (6)Cl20—C37—C38—C28175.07 (6)
C16—C17—C18—Cl9177.98 (7)C36—C37—C38—Cl21175.75 (7)
Cl7—C17—C18—Cl963.61 (8)Cl19—C37—C38—Cl2166.27 (8)
Cl8—C17—C18—Cl960.10 (9)Cl20—C37—C38—Cl2157.87 (9)
C7—C8—C18—C1950.31 (10)C27—C28—C38—C3955.30 (10)
C9—C8—C18—C1972.58 (9)C29—C28—C38—C3968.84 (9)
C7—C8—C18—C17154.44 (8)C27—C28—C38—C37159.80 (8)
C9—C8—C18—C1731.56 (9)C29—C28—C38—C3735.66 (9)
C7—C8—C18—Cl980.40 (9)C27—C28—C38—Cl2174.21 (9)
C9—C8—C18—Cl9156.71 (7)C29—C28—C38—Cl21161.65 (7)
C17—C18—C19—C2037.05 (10)C37—C38—C39—C4035.04 (10)
C8—C18—C19—C2069.24 (10)C28—C38—C39—C4070.71 (10)
Cl9—C18—C19—C20160.31 (7)Cl21—C38—C39—C40158.93 (8)
C17—C18—C19—Cl10149.88 (7)C37—C38—C39—Cl22151.30 (8)
C8—C18—C19—Cl10103.83 (9)C28—C38—C39—Cl22102.96 (9)
Cl9—C18—C19—Cl1026.62 (11)Cl21—C38—C39—Cl2227.41 (11)
C18—C19—C20—C162.56 (10)C38—C39—C40—C360.47 (11)
Cl10—C19—C20—C16175.25 (8)Cl22—C39—C40—C36173.75 (8)
C18—C19—C20—Cl11170.33 (7)C38—C39—C40—Cl23171.46 (8)
Cl10—C19—C20—Cl112.35 (15)Cl22—C39—C40—Cl231.82 (16)
C17—C16—C20—C1932.74 (10)C37—C36—C40—C3934.02 (10)
C9—C16—C20—C1972.30 (10)C29—C36—C40—C3971.46 (10)
Cl12—C16—C20—C19158.11 (7)Cl24—C36—C40—C39159.39 (7)
C17—C16—C20—Cl11154.13 (7)C37—C36—C40—Cl23153.79 (8)
C9—C16—C20—Cl11100.83 (9)C29—C36—C40—Cl23100.73 (9)
Cl12—C16—C20—Cl1128.77 (11)Cl24—C36—C40—Cl2328.42 (11)

Experimental details

Crystal data
Chemical formulaC20H8Cl12
Mr673.66
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)9.6434 (1), 15.4287 (2), 16.4161 (2)
α, β, γ (°)92.1948 (6), 98.2331 (7), 91.3097 (6)
V3)2414.53 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.39
Crystal size (mm)0.40 × 0.35 × 0.15
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.607, 0.819
No. of measured, independent and
observed [I > 2σ(I)] reflections
111692, 30125, 24699
Rint0.026
(sin θ/λ)max1)0.910
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.086, 1.03
No. of reflections30125
No. of parameters578
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.87, 0.63

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Footnotes

1CAS 147730-93-6.

Acknowledgements

The purchase of the diffractometer was made possible by Grant No. LEQSF(1999–2000)-ESH-TR-13, administered by the Louisiana Board of Regents. We thank Lee Shui and Mark McLaughlin for providing the sample.

References

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First citationLacourcelle, C., Poite, J. C., Baldy, A., Jaud, J., Negrel, J. C. & Chanon, M. (1993). Acta Chem. Scand. 47, 92–94.  CrossRef CAS Web of Science Google Scholar
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First citationOtwinowski, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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