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The title compound, C16H11Cl5, is an asymmetric tetra­chloro­tetralin showing disorder of the alicyclic moiety, which has a boat conformation in the crystalline state and half-chair in solution.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016762/na6094sup1.cif
Contains datablocks br65, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016762/na6094Isup2.hkl
Contains datablock I

CCDC reference: 176012

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.127
  • Data-to-parameter ratio = 12.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
SHFSU_01 Alert C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.097 Additional refinement cycles may be required. PLAT_301 Alert C Main Residue Disorder ........................ 13.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Preliminary results were presented at a National Conference (Bombieri et al., 1984). The results obtained from X-ray data analysis show that the stereochemistry of this adduct in the solid state is different from that in solution, as found from NMR studies. In fact, the dissymetric distribution of Cl atoms results in severe steric interactions which appear to be released within the alicyclic moiety of the molecule, more flexible in solution, simply by a distortion of the basic half-chair conformation. In the solid state, the very strict steric rigidity requirement of the system does not allow such an accommodation and the dissymetric adduct is forced to assume a boat conformation, which minimizes steric strain and seems to better accommodate the otherwise strongly interacting c-2, c-3 and t-4 chlorine atoms. The molecule shows a disorder problem within the alicyclic ring owing to the conformational fluxion.

Experimental top

The title compound was prepared according to the procedure already reported (Aversa et al., 1982). Crystals suitable for X-ray diffraction, were obtained by slowly cooling a light petroleum solution.

Refinement top

Alert C shown by checkCIF control are due to disorder problem of the molecule.

Computing details top

Data collection: P3/V (Siemens, 1989); cell refinement: P3/V; data reduction: XDISK (Siemens, 1990); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (Siemens, 1996); software used to prepare material for publication: PARST95 (Nardelli, 1995) and SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP (Johnson, 1976) drawing of the title molecule with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% level.
r-1,c-2,c-3,t-4,5-pentachloro-6-phenyltetralin top
Crystal data top
C16H11Cl5F(000) = 768
Mr = 380.50Dx = 1.583 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.321 (3) ÅCell parameters from 30 reflections
b = 9.101 (2) Åθ = 13.0–30.0°
c = 14.279 (3) ŵ = 0.90 mm1
β = 112.77 (3)°T = 298 K
V = 1596.2 (6) Å3Regular prismatic, colourless
Z = 40.31 × 0.20 × 0.14 mm
Data collection top
Siemens R3m/V
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 24.9°, θmin = 1.7°
Graphite monochromatorh = 1514
ω–2θ scansk = 010
2652 measured reflectionsl = 016
2652 independent reflections3 standard reflections every 197 reflections
1977 reflections with I > 2σ(I) intensity decay: 1.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0788P)2 + 1.718P]
where P = (Fo2 + 2Fc2)/3
2651 reflections(Δ/σ)max = 0.097
219 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
C16H11Cl5V = 1596.2 (6) Å3
Mr = 380.50Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.321 (3) ŵ = 0.90 mm1
b = 9.101 (2) ÅT = 298 K
c = 14.279 (3) Å0.31 × 0.20 × 0.14 mm
β = 112.77 (3)°
Data collection top
Siemens R3m/V
diffractometer
Rint = 0.000
2652 measured reflections3 standard reflections every 197 reflections
2652 independent reflections intensity decay: 1.3%
1977 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.52 e Å3
2651 reflectionsΔρmin = 0.41 e Å3
219 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 on F2 for ALL reflections except for 1 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
xyzUiso*/UeqOcc. (<1)
Cl10.57593 (10)0.33146 (13)0.59486 (7)0.0686 (4)
Cl20.56503 (10)0.66582 (13)0.68167 (8)0.0703 (4)
Cl30.58413 (9)0.48844 (13)0.93911 (8)0.0671 (4)
Cl40.86867 (10)0.56966 (15)0.87736 (10)0.0777 (4)
Cl50.86394 (11)0.25868 (14)1.09706 (7)0.0780 (4)
C60.7897 (3)0.0557 (4)0.9475 (3)0.0476 (9)
C70.7379 (3)0.0184 (4)0.8461 (3)0.0517 (9)
H70.7324 (3)0.0804 (4)0.8280 (3)0.062*
C80.6939 (3)0.1226 (4)0.7705 (3)0.0518 (10)
H80.6591 (3)0.0935 (4)0.7031 (3)0.062*
C90.7018 (3)0.2693 (4)0.7954 (3)0.0523 (10)
C10.6507 (5)0.3928 (5)0.7197 (3)0.080 (2)
H10.7130 (5)0.4448 (5)0.7151 (3)0.097*
C20.5970 (4)0.5012 (6)0.7558 (4)0.047 (2)0.725 (8)
H20.5276 (4)0.4583 (6)0.7507 (4)0.057*0.725 (8)
C30.6586 (4)0.5459 (6)0.8684 (4)0.046 (2)0.725 (8)
H30.6661 (4)0.6531 (6)0.8727 (4)0.055*0.725 (8)
C40.7695 (6)0.4772 (9)0.9189 (6)0.047 (2)0.725 (8)
H40.7933 (6)0.4910 (9)0.9924 (6)0.056*0.725 (8)
C2'0.6734 (10)0.5267 (14)0.7414 (9)0.041 (4)0.275 (8)
H2'0.7245 (10)0.5472 (14)0.7088 (9)0.049*0.275 (8)
C3'0.7417 (12)0.5640 (15)0.8533 (11)0.048 (4)0.275 (8)
H3'0.7196 (12)0.6617 (15)0.8670 (11)0.058*0.275 (8)
C4'0.7276 (15)0.458 (2)0.9292 (16)0.037 (4)0.275 (8)
H4'0.7840 (15)0.481 (2)0.9959 (16)0.044*0.275 (8)
C100.7561 (4)0.3119 (4)0.8967 (3)0.0586 (11)
C50.7993 (3)0.2046 (5)0.9707 (3)0.0511 (10)
C110.8309 (3)0.0621 (4)1.0268 (3)0.0496 (9)
C120.9419 (4)0.0793 (6)1.0834 (3)0.0706 (13)
H120.9913 (4)0.0126 (6)1.0761 (3)0.085*
C130.9789 (4)0.1964 (6)1.1508 (4)0.0797 (15)
H131.0532 (4)0.2111 (6)1.1855 (4)0.096*
C140.9062 (5)0.2898 (5)1.1661 (3)0.0700 (13)
H140.9310 (5)0.3681 (5)1.2110 (3)0.084*
C150.7977 (4)0.2678 (5)1.1153 (3)0.0687 (12)
H150.7485 (4)0.3296 (5)1.1277 (3)0.082*
C160.7589 (4)0.1545 (4)1.0454 (3)0.0563 (10)
H160.6843 (4)0.1411 (4)1.0111 (3)0.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0868 (8)0.0644 (7)0.0342 (5)0.0054 (6)0.0010 (5)0.0025 (4)
Cl20.0922 (8)0.0576 (7)0.0586 (6)0.0254 (6)0.0263 (6)0.0160 (5)
Cl30.0746 (7)0.0740 (8)0.0604 (6)0.0085 (6)0.0346 (5)0.0007 (5)
Cl40.0661 (7)0.0830 (9)0.0799 (8)0.0220 (6)0.0239 (6)0.0010 (6)
Cl50.1006 (9)0.0724 (8)0.0351 (5)0.0122 (6)0.0020 (5)0.0052 (5)
C60.045 (2)0.050 (2)0.042 (2)0.007 (2)0.012 (2)0.005 (2)
C70.057 (2)0.041 (2)0.048 (2)0.003 (2)0.011 (2)0.004 (2)
C80.058 (2)0.049 (2)0.037 (2)0.002 (2)0.005 (2)0.007 (2)
C90.062 (2)0.047 (2)0.036 (2)0.010 (2)0.006 (2)0.003 (2)
C10.117 (4)0.054 (3)0.037 (2)0.021 (3)0.008 (2)0.003 (2)
C20.049 (3)0.051 (3)0.040 (3)0.008 (2)0.015 (2)0.005 (2)
C30.056 (3)0.037 (3)0.046 (3)0.001 (2)0.021 (2)0.001 (2)
C40.052 (5)0.046 (4)0.041 (3)0.007 (4)0.017 (3)0.007 (3)
C2'0.036 (7)0.041 (8)0.047 (7)0.012 (6)0.017 (6)0.009 (6)
C3'0.060 (9)0.028 (7)0.052 (8)0.005 (6)0.017 (7)0.003 (6)
C4'0.040 (11)0.028 (8)0.047 (9)0.008 (8)0.023 (8)0.000 (6)
C100.075 (3)0.044 (2)0.039 (2)0.010 (2)0.004 (2)0.006 (2)
C50.053 (2)0.056 (2)0.033 (2)0.010 (2)0.004 (2)0.002 (2)
C110.053 (2)0.050 (2)0.043 (2)0.012 (2)0.015 (2)0.003 (2)
C120.060 (3)0.094 (4)0.055 (2)0.014 (2)0.020 (2)0.020 (2)
C130.076 (3)0.104 (4)0.057 (3)0.031 (3)0.023 (2)0.027 (3)
C140.105 (4)0.056 (3)0.044 (2)0.020 (3)0.023 (2)0.010 (2)
C150.101 (4)0.053 (3)0.052 (2)0.012 (3)0.029 (2)0.001 (2)
C160.064 (2)0.052 (2)0.051 (2)0.001 (2)0.021 (2)0.002 (2)
Geometric parameters (Å, º) top
Cl1—C11.763 (4)C3—C41.506 (10)
Cl2—C21.789 (5)C3—H30.9800
Cl2—C2'1.860 (12)C4—C101.534 (9)
Cl3—C31.748 (5)C4—H40.9800
Cl3—C4'1.990 (17)C2'—C3'1.541 (18)
Cl4—C3'1.591 (15)C2'—H2'0.9800
Cl4—C41.847 (8)C3'—C4'1.51 (2)
Cl5—C51.743 (4)C3'—H3'0.9800
C6—C71.384 (5)C4'—C101.506 (19)
C6—C51.389 (6)C4'—H4'0.9800
C6—C111.501 (5)C10—C51.389 (5)
C7—C81.385 (5)C11—C161.377 (6)
C7—H70.9300C11—C121.393 (6)
C8—C91.375 (5)C12—C131.392 (7)
C8—H80.9300C12—H120.9300
C9—C101.397 (5)C13—C141.368 (7)
C9—C11.525 (6)C13—H130.9300
C1—C2'1.265 (14)C14—C151.358 (7)
C1—C21.428 (7)C14—H140.9300
C1—H10.9800C15—C161.388 (6)
C2—C31.549 (7)C15—H150.9300
C2—H20.9800C16—H160.9300
C2—Cl2—C2'36.3 (4)C1—C2'—Cl2118.3 (9)
C3—Cl3—C4'39.1 (6)C3'—C2'—Cl2111.5 (9)
C3'—Cl4—C438.9 (5)C1—C2'—H2'102.2
C7—C6—C5116.8 (3)C3'—C2'—H2'102.2
C7—C6—C11120.2 (4)Cl2—C2'—H2'102.2
C5—C6—C11123.0 (3)C4'—C3'—C2'114.5 (12)
C8—C7—C6122.4 (4)C4'—C3'—Cl4106.4 (11)
C8—C7—H7118.8C2'—C3'—Cl4112.4 (10)
C6—C7—H7118.8C4'—C3'—H3'107.7
C9—C8—C7119.7 (3)C2'—C3'—H3'107.8
C9—C8—H8120.1Cl4—C3'—H3'107.8
C7—C8—H8120.1C3'—C4'—C10103.1 (12)
C8—C9—C10119.6 (4)C3'—C4'—Cl3110.5 (12)
C8—C9—C1124.3 (3)C10—C4'—Cl3120.5 (10)
C10—C9—C1116.1 (4)C3'—C4'—H4'107.3
C2'—C1—C249.6 (6)C10—C4'—H4'107.3
C2'—C1—C9122.5 (6)Cl3—C4'—H4'107.3
C2—C1—C9113.7 (4)C5—C10—C9119.2 (4)
C2'—C1—Cl1122.7 (6)C5—C10—C4'117.8 (8)
C2—C1—Cl1114.7 (4)C9—C10—C4'118.2 (8)
C9—C1—Cl1114.0 (3)C5—C10—C4123.4 (4)
C2'—C1—H154.7C9—C10—C4117.3 (4)
C2—C1—H1104.3C4'—C10—C424.8 (5)
C9—C1—H1104.3C6—C5—C10122.1 (3)
Cl1—C1—H1104.3C6—C5—Cl5119.0 (3)
C1—C2—C3114.7 (4)C10—C5—Cl5118.8 (3)
C1—C2—Cl2113.7 (4)C16—C11—C12118.8 (4)
C3—C2—Cl2107.7 (4)C16—C11—C6120.2 (3)
C1—C2—H2106.8C12—C11—C6120.9 (4)
C3—C2—H2106.8C11—C12—C13120.0 (5)
Cl2—C2—H2106.8C11—C12—H12120.0
C4—C3—C2114.6 (5)C13—C12—H12120.0
C4—C3—Cl3105.6 (4)C14—C13—C12120.2 (5)
C2—C3—Cl3109.2 (4)C14—C13—H13119.9
C4—C3—H3109.1C12—C13—H13119.9
C2—C3—H3109.1C15—C14—C13119.7 (4)
Cl3—C3—H3109.1C15—C14—H14120.1
C3—C4—C10107.1 (5)C13—C14—H14120.1
C3—C4—Cl4110.3 (5)C14—C15—C16121.1 (5)
C10—C4—Cl4114.9 (5)C14—C15—H15119.5
C3—C4—H4108.1C16—C15—H15119.5
C10—C4—H4108.1C11—C16—C15120.0 (4)
Cl4—C4—H4108.1C11—C16—H16120.0
C1—C2'—C3'117.1 (10)C15—C16—H16120.0
C5—C6—C7—C82.1 (6)Cl4—C3'—C4'—C1068.5 (13)
C11—C6—C7—C8176.9 (4)C2'—C3'—C4'—Cl373.7 (15)
C6—C7—C8—C90.5 (6)Cl4—C3'—C4'—Cl3161.4 (8)
C7—C8—C9—C101.2 (7)C3—Cl3—C4'—C3'7.0 (7)
C7—C8—C9—C1176.2 (4)C3—Cl3—C4'—C10113.0 (17)
C8—C9—C1—C2'168.6 (8)C8—C9—C10—C51.3 (7)
C10—C9—C1—C2'13.8 (10)C1—C9—C10—C5176.4 (4)
C8—C9—C1—C2135.4 (5)C8—C9—C10—C4'156.2 (8)
C10—C9—C1—C242.1 (7)C1—C9—C10—C4'21.5 (9)
C8—C9—C1—Cl11.4 (7)C8—C9—C10—C4175.7 (5)
C10—C9—C1—Cl1176.1 (4)C1—C9—C10—C46.6 (7)
C2'—C1—C2—C371.7 (8)C3'—C4'—C10—C5151.4 (9)
C9—C1—C2—C341.7 (7)Cl3—C4'—C10—C585.0 (13)
Cl1—C1—C2—C3175.3 (4)C3'—C4'—C10—C953.4 (13)
C2'—C1—C2—Cl252.8 (8)Cl3—C4'—C10—C970.3 (14)
C9—C1—C2—Cl2166.2 (4)C3'—C4'—C10—C441.1 (17)
Cl1—C1—C2—Cl260.2 (6)Cl3—C4'—C10—C4165 (3)
C2'—Cl2—C2—C144.1 (7)C3—C4—C10—C5132.1 (5)
C2'—Cl2—C2—C384.1 (8)Cl4—C4—C10—C5105.0 (6)
C1—C2—C3—C44.8 (7)C3—C4—C10—C951.0 (7)
Cl2—C2—C3—C4122.8 (5)Cl4—C4—C10—C971.9 (6)
C1—C2—C3—Cl3113.4 (5)C3—C4—C10—C4'48 (2)
Cl2—C2—C3—Cl3118.9 (3)Cl4—C4—C10—C4'171 (3)
C4'—Cl3—C3—C45.3 (11)C7—C6—C5—C102.0 (6)
C4'—Cl3—C3—C2118.4 (10)C11—C6—C5—C10176.9 (4)
C2—C3—C4—C1049.2 (7)C7—C6—C5—Cl5179.9 (3)
Cl3—C3—C4—C1071.0 (5)C11—C6—C5—Cl51.1 (5)
C2—C3—C4—Cl476.4 (6)C9—C10—C5—C60.4 (7)
Cl3—C3—C4—Cl4163.3 (3)C4'—C10—C5—C6154.6 (8)
C3'—Cl4—C4—C38.2 (8)C4—C10—C5—C6177.2 (5)
C3'—Cl4—C4—C10113.0 (10)C9—C10—C5—Cl5178.5 (3)
C2—C1—C2'—C3'85.4 (12)C4'—C10—C5—Cl523.4 (9)
C9—C1—C2'—C3'9.4 (15)C4—C10—C5—Cl54.7 (7)
Cl1—C1—C2'—C3'178.6 (8)C7—C6—C11—C1666.0 (5)
C2—C1—C2'—Cl252.7 (7)C5—C6—C11—C16112.9 (5)
C9—C1—C2'—Cl2147.5 (6)C7—C6—C11—C12114.6 (5)
Cl1—C1—C2'—Cl243.3 (12)C5—C6—C11—C1266.5 (5)
C2—Cl2—C2'—C154.8 (8)C16—C11—C12—C135.7 (7)
C2—Cl2—C2'—C3'85.5 (11)C6—C11—C12—C13174.9 (4)
C1—C2'—C3'—C4'28.6 (18)C11—C12—C13—C143.8 (8)
Cl2—C2'—C3'—C4'112.2 (13)C12—C13—C14—C150.1 (8)
C1—C2'—C3'—Cl493.0 (12)C13—C14—C15—C162.1 (7)
Cl2—C2'—C3'—Cl4126.2 (9)C12—C11—C16—C153.7 (6)
C4—Cl4—C3'—C4'2.5 (11)C6—C11—C16—C15176.9 (4)
C4—Cl4—C3'—C2'123.7 (13)C14—C15—C16—C110.2 (6)
C2'—C3'—C4'—C1056.4 (16)

Experimental details

Crystal data
Chemical formulaC16H11Cl5
Mr380.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)13.321 (3), 9.101 (2), 14.279 (3)
β (°) 112.77 (3)
V3)1596.2 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.90
Crystal size (mm)0.31 × 0.20 × 0.14
Data collection
DiffractometerSiemens R3m/V
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2652, 2652, 1977
Rint0.000
(sin θ/λ)max1)0.592
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.127, 1.01
No. of reflections2651
No. of parameters219
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.52, 0.41

Computer programs: P3/V (Siemens, 1989), P3/V, XDISK (Siemens, 1990), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XPW (Siemens, 1996), PARST95 (Nardelli, 1995) and SHELXL97.

 

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