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The title compound, C15Cl8O, was separated from the products of a solvothermal reaction of metallic sodium and carbon tetrachloride in air in a pressured autoclave. The mol­ecule is bisected by a crystallographic mirror plane and has essentially C2v symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009973/cv6304sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009973/cv6304Isup2.hkl
Contains datablock I

CCDC reference: 196339

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.050
  • wR factor = 0.110
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound .. ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. Cl4 .. 3.42 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL006_ALERT_1_A _publ_requested_journal is missing e.g. 'Acta Crystallographica Section C'
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1988); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

1,2,3,5,6,7,8,9-Octachloro-cyclopenta[def]phenanthren-4-one top
Crystal data top
C15Cl8ODx = 2.027 Mg m3
Mr = 479.75Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, CmcaCell parameters from 25 reflections
a = 22.979 (5) Åθ = 8.0–15.0°
b = 8.7180 (17) ŵ = 1.43 mm1
c = 15.697 (3) ÅT = 293 K
V = 3144.6 (11) Å3Prism, yellow
Z = 80.32 × 0.26 × 0.18 mm
F(000) = 1872
Data collection top
Enraf–Nonius CAD-4
diffractometer
1078 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
ω scanh = 280
Absorption correction: empirical
(ψ scan; North et al., 1968)
k = 010
Tmin = 0.657, Tmax = 0.783l = 190
1588 measured reflections3 standard reflections every 60 min
1588 independent reflections intensity decay: none
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullPrimary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.050Secondary atom site location: difference Fourier map
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0421P)2 + 1.1559P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1588 reflectionsΔρmax = 0.30 e Å3
112 parametersΔρmin = 0.29 e Å3
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
xyzUiso*/Ueq
Cl10.43537 (5)0.11507 (13)0.40342 (7)0.0550 (3)
Cl20.36045 (5)0.61323 (15)0.75240 (9)0.0697 (4)
Cl30.27914 (5)0.42763 (17)0.63532 (9)0.0743 (4)
Cl40.32524 (5)0.21792 (16)0.49757 (9)0.0744 (5)
C10.46970 (16)0.2195 (4)0.4813 (2)0.0404 (10)
C20.38952 (18)0.5000 (5)0.6740 (2)0.0459 (10)
C30.35317 (17)0.4146 (5)0.6191 (3)0.0468 (11)
C40.37460 (18)0.3197 (4)0.5559 (3)0.0435 (10)
C50.43605 (17)0.3064 (4)0.5427 (2)0.0395 (9)
C60.46890 (17)0.3929 (4)0.5985 (2)0.0376 (9)
C70.44829 (17)0.4884 (5)0.6634 (2)0.0412 (9)
C80.50000.5560 (7)0.7077 (4)0.0462 (15)
O10.50000.6456 (5)0.7663 (3)0.0623 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0599 (7)0.0569 (7)0.0481 (6)0.0067 (6)0.0075 (5)0.0114 (6)
Cl20.0654 (8)0.0785 (8)0.0653 (7)0.0143 (7)0.0153 (6)0.0192 (7)
Cl30.0405 (6)0.0975 (10)0.0849 (9)0.0068 (7)0.0074 (6)0.0121 (8)
Cl40.0440 (6)0.0892 (10)0.0899 (9)0.0090 (7)0.0077 (7)0.0285 (8)
C10.050 (2)0.037 (2)0.034 (2)0.0036 (19)0.0049 (17)0.0022 (18)
C20.053 (2)0.046 (2)0.039 (2)0.008 (2)0.008 (2)0.002 (2)
C30.037 (2)0.049 (3)0.054 (3)0.001 (2)0.0002 (19)0.005 (2)
C40.042 (2)0.041 (2)0.047 (2)0.0007 (19)0.0031 (19)0.004 (2)
C50.045 (2)0.034 (2)0.040 (2)0.0043 (19)0.0002 (19)0.0049 (19)
C60.043 (2)0.033 (2)0.036 (2)0.0022 (19)0.0007 (18)0.0048 (17)
C70.048 (2)0.038 (2)0.038 (2)0.001 (2)0.0022 (19)0.0012 (19)
C80.064 (4)0.044 (3)0.031 (3)0.0000.0000.002 (3)
O10.068 (3)0.063 (3)0.056 (3)0.0000.0000.019 (2)
Geometric parameters (Å, º) top
Cl1—C11.717 (4)C3—C41.382 (6)
Cl2—C21.713 (4)C4—C51.432 (5)
Cl3—C31.724 (4)C5—C61.379 (5)
Cl4—C41.706 (4)C6—C71.398 (5)
C1—C1i1.392 (8)C6—C6i1.429 (8)
C1—C51.450 (5)C7—C81.498 (5)
C2—C71.365 (5)C8—O11.206 (7)
C2—C31.413 (6)C8—C7i1.498 (5)
C1i—C1—C5122.2 (2)C6—C5—C4113.8 (4)
C1i—C1—Cl1117.36 (13)C6—C5—C1114.5 (3)
C5—C1—Cl1120.4 (3)C4—C5—C1131.6 (4)
C7—C2—C3118.1 (4)C5—C6—C7127.0 (4)
C7—C2—Cl2121.1 (3)C5—C6—C6i123.2 (2)
C3—C2—Cl2120.8 (3)C7—C6—C6i109.8 (2)
C4—C3—C2122.9 (4)C2—C7—C6118.0 (4)
C4—C3—Cl3119.8 (3)C2—C7—C8134.3 (4)
C2—C3—Cl3117.3 (3)C6—C7—C8107.7 (4)
C3—C4—C5120.2 (4)O1—C8—C7127.5 (2)
C3—C4—Cl4117.3 (3)O1—C8—C7i127.5 (2)
C5—C4—Cl4122.4 (3)C7—C8—C7i105.0 (5)
Symmetry code: (i) x+1, y, z.
 

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