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Acta Cryst.(2004). E60, o899±o900 DOI: 10.1107/S1600536804009973 Ying Penget al. C15Cl8O

o899

organic papers

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

1,2,3,5,6,7,8,9-Octachlorocyclopenta[

def

]-phenanthren-4-one

Ying Peng,aSu-Yuan Xie,a

Shun-Liu Deng,aRong-Bin

Huanga* and Lan-Sun Zhengb

aDepartment of Chemistry, Xiamen University,

Xiamen 361005, People's Republic of China, andbState Key Laboratory for Physical Chemistry of Solid Surfaces, Department of Chemistry, Xiamen University, Xiamen 361005, People's Republic of China

Correspondence e-mail: rbhuang@xmu.edu.cn

Key indicators

Single-crystal X-ray study

T= 293 K

Mean(C±C) = 0.005 AÊ

Rfactor = 0.050

wRfactor = 0.110

Data-to-parameter ratio = 14.2

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved

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

C2vsymmetry.

Comment

Alkali metals and polyhalogenated alkanes under high pres-sure/temperature in an autoclave can undergo different reactions under different conditions and give different products, for example, diamond powders from CCl4(Liet al.,

1998), multi-wall carbon nanotubes and hollow spherical graphite from hexachlorobenzene (Jiang et al., 2000), and carbon concentric spheres (`onions') from hexachloropenta-diene (Liet al., 2001). Long-standing interest has been focused on the fabrication of fullerenes, and various techniques, such as high-voltage electric discharge in liquid (Huanget al., 1997) or vaporized (Xieet al., 2001) chloroform and CCl4, have been

used to generate and trap the intermediates of fullerenes. In such a process, we have isolated perchlorinated aromatic hydrocarbons (PCAHs), which can be used as building blocks for fullerenes, and also identi®ed a trace of C60and C70(Xieet

al., 2001). On the other hand, under solvothermal conditions, a series of perchlorinated fullerene fragments, such as C26H8Cl10

(Penget al., 2001) and C18Cl12O2(Penget al., 2004), have been

obtained and characterized by X-ray diffraction.

We report here the synthesis and crystal structure of the title compound, (I) (Fig. 1), a new perchlorinated compound, which was separated from the products of a solvothermal reaction. All bond lengths and angles in (I) are normal (Table 1). The molecule is bisected by a crystallographic mirror plane and has essentiallyC2vsymmetry.

Experimental

Metallic sodium (3.0 g) was added to carbon tetrachloride (25 ml) in a stainless-steel autoclave with a capacity of 50 ml. The autoclave was heated to 673 K, maintained at that temperature for 40 h and then allowed to cool to room temperature. The resulting dark powder was

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washed with water several times and dried in a vacuum at room temperature. The dried product was extracted with toluene/cyclo-hexane in a volume ratio of 1:1. The extract was separated by column chromatography on neutral alumina, using toluene/cyclohexane as eluant. Yellow crystals suitable for X-ray diffraction were obtained from the yellow solution upon slow evaporation of the solvent in air. The product was analyzed by mass spectrometry. The molecular peak appeared at a mass/charge ratio of 480. The isotopic distribution pattern of chlorine shows that the molecule contains eight Cl atoms.

Crystal data

C15Cl8O Mr= 479.75

Orthorhombic,Cmca a= 22.979 (5) AÊ

b= 8.7180 (17) AÊ

c= 15.697 (3) AÊ

V= 3144.6 (11) AÊ3 Z= 8

Dx= 2.027 Mg mÿ3

MoKradiation Cell parameters from 25

re¯ections

= 8.0±15.0 = 1.43 mmÿ1 T= 293 (2) K Prism, yellow 0.320.260.18 mm

Data collection

Enraf±Nonius CAD-4 diffractometer

!scans

Absorption correction: scan (Northet al., 1968)

Tmin= 0.657,Tmax= 0.783

1588 measured re¯ections 1588 independent re¯ections

1078 re¯ections withI> 2(I)

max= 26.0 h=ÿ28!0

k= 0!10

l=ÿ19!0 3 standard re¯ections

frequency: 60 min intensity decay: none

Re®nement

Re®nement onF2 R[F2> 2(F2)] = 0.050 wR(F2) = 0.110 S= 1.04 1588 re¯ections 112 parameters

w= 1/[2(F

o2) + (0.0421P)2

+ 1.1559P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001

max= 0.30 e AÊÿ3

min=ÿ0.29 e AÊÿ3

Table 1

Selected geometric parameters (AÊ,).

Cl1ÐC1 1.717 (4) Cl2ÐC2 1.713 (4) Cl3ÐC3 1.724 (4) Cl4ÐC4 1.706 (4) C1ÐC1i 1.392 (8)

C1ÐC5 1.450 (5) C2ÐC7 1.365 (5) C2ÐC3 1.413 (6)

C3ÐC4 1.382 (6) C4ÐC5 1.432 (5) C5ÐC6 1.379 (5) C6ÐC7 1.398 (5) C6ÐC6i 1.429 (8)

C7ÐC8 1.498 (5) C8ÐO1 1.206 (7) C8ÐC7i 1.498 (5)

C1iÐC1ÐC5 122.2 (2)

C1iÐC1ÐCl1 117.36 (13)

C5ÐC1ÐCl1 120.4 (3) C7ÐC2ÐC3 118.1 (4) C7ÐC2ÐCl2 121.1 (3) C3ÐC2ÐCl2 120.8 (3) C4ÐC3ÐC2 122.9 (4) C4ÐC3ÐCl3 119.8 (3) C2ÐC3ÐCl3 117.3 (3) C3ÐC4ÐC5 120.2 (4) C3ÐC4ÐCl4 117.3 (3) C5ÐC4ÐCl4 122.4 (3)

C6ÐC5ÐC4 113.8 (4) C6ÐC5ÐC1 114.5 (3) C4ÐC5ÐC1 131.6 (4) C5ÐC6ÐC7 127.0 (4) C5ÐC6ÐC6i 123.2 (2)

C7ÐC6ÐC6i 109.8 (2)

C2ÐC7ÐC6 118.0 (4) C2ÐC7ÐC8 134.3 (4) C6ÐC7ÐC8 107.7 (4) O1ÐC8ÐC7 127.5 (2) O1ÐC8ÐC7i 127.5 (2)

C7ÐC8ÐC7i 105.0 (5) Symmetry code: (i) 1ÿx;y;z.

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

The authors thank the NSFC (grant Nos. 20271044, 20273052 and 20021002) and the Department of Science and Technology of China (2002 CCA01600).

References

Enraf±Nonius (1988). CAD-4 Software.Enraf±Nonius, Delft, The Nether-lands.

Harms, K. (1997).XCAD4. University of Marburg, Germany.

Huang, R.-B., Huang, W.-J., Wang, Y.-H., Tang, Z.-C. & Zheng, L.-S. (1997).J. Am. Chem. Soc.117, 5954±5955.

Jiang, Y., Wu, Y., Zhang, S.-Y., Xu, C.-Y., Yu, W.-C., Xie, Y. & Qian, Y.-T. (2000).J. Am. Chem. Soc.122, 12383±12384.

Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.

Li, C.-Y., Chiu, H.-T., Peng, C.-W., Yen, M.-Y., Chang, Y.-H. & Liu, C.-S. (2001).Adv. Mater.13, 1105±1107.

Li, Y.-D., Qian, Y.-T., Liao, H.-W., Ding, Y., Yang, L., Xu, C.-Y., Li, F.-Q. & Zhou, G.-E. (1998).Science,281, 246±247.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351± 359.

Peng, Y., Xie, S.-Y., Huang, R.-B. & Zheng, L.-S. (2001).Acta Cryst.E57, o617± o618.

Peng, Y., Xie, S.-Y., Long, L.-S., Huang, R.-B. & Zheng, L. S. (2004).Acta Cryst.E60, o762±o763.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

Xie, S.-Y., Deng, S.-L., Yu, L.-J., Huang, R.-B. & Zheng, L.-S. (2001).J. Phys. Chem. B,105, 1734±1738.

Figure 1

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supporting information

sup-1 Acta Cryst. (2004). E60, o899–o900

supporting information

Acta Cryst. (2004). E60, o899–o900 [https://doi.org/10.1107/S1600536804009973]

1,2,3,5,6,7,8,9-Octachlorocyclopenta[

def

]phenanthren-4-one

Ying Peng, Su-Yuan Xie, Shun-Liu Deng, Rong-Bin Huang and Lan-Sun Zheng

1,2,3,5,6,7,8,9-Octachloro-cyclopenta[def]phenanthren-4-one

Crystal data

C15Cl8O

Mr = 479.75

Orthorhombic, Cmca a = 22.979 (5) Å

b = 8.7180 (17) Å

c = 15.697 (3) Å

V = 3144.6 (11) Å3

Z = 8

F(000) = 1872

Dx = 2.027 Mg m−3

Mo radiation, λ = 0.71073 Å Cell parameters from 25 reflections

θ = 8.0–15.0°

µ = 1.43 mm−1

T = 293 K Prism, yellow

0.32 × 0.26 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scan

Absorption correction: empirical (ψ scan; North et al., 1968)

Tmin = 0.657, Tmax = 0.783 1588 measured reflections

1588 independent reflections 1078 reflections with I > 2σ(I)

Rint = 0.000

θmax = 26.0°, θmin = 1.8°

h = −28→0

k = 0→10

l = −19→0

3 standard reflections every 60 min intensity decay: none

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 > 2σ(F2)] = 0.050

wR(F2) = 0.110

S = 1.04 1588 reflections 112 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

w = 1/[σ2(F

o2) + (0.0421P)2 + 1.1559P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.30 e Å−3 Δρmin = −0.29 e Å−3

Special details

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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)

x y z Uiso*/Ueq

Cl1 0.43537 (5) 0.11507 (13) 0.40342 (7) 0.0550 (3)

Cl2 0.36045 (5) 0.61323 (15) 0.75240 (9) 0.0697 (4)

Cl3 0.27914 (5) 0.42763 (17) 0.63532 (9) 0.0743 (4)

Cl4 0.32524 (5) 0.21792 (16) 0.49757 (9) 0.0744 (5)

C1 0.46970 (16) 0.2195 (4) 0.4813 (2) 0.0404 (10)

C2 0.38952 (18) 0.5000 (5) 0.6740 (2) 0.0459 (10)

C3 0.35317 (17) 0.4146 (5) 0.6191 (3) 0.0468 (11)

C4 0.37460 (18) 0.3197 (4) 0.5559 (3) 0.0435 (10)

C5 0.43605 (17) 0.3064 (4) 0.5427 (2) 0.0395 (9)

C6 0.46890 (17) 0.3929 (4) 0.5985 (2) 0.0376 (9)

C7 0.44829 (17) 0.4884 (5) 0.6634 (2) 0.0412 (9)

C8 0.5000 0.5560 (7) 0.7077 (4) 0.0462 (15)

O1 0.5000 0.6456 (5) 0.7663 (3) 0.0623 (12)

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

Cl1 0.0599 (7) 0.0569 (7) 0.0481 (6) −0.0067 (6) −0.0075 (5) −0.0114 (6)

Cl2 0.0654 (8) 0.0785 (8) 0.0653 (7) 0.0143 (7) 0.0153 (6) −0.0192 (7)

Cl3 0.0405 (6) 0.0975 (10) 0.0849 (9) 0.0068 (7) 0.0074 (6) −0.0121 (8)

Cl4 0.0440 (6) 0.0892 (10) 0.0899 (9) −0.0090 (7) −0.0077 (7) −0.0285 (8)

C1 0.050 (2) 0.037 (2) 0.034 (2) −0.0036 (19) −0.0049 (17) −0.0022 (18)

C2 0.053 (2) 0.046 (2) 0.039 (2) 0.008 (2) 0.008 (2) 0.002 (2)

C3 0.037 (2) 0.049 (3) 0.054 (3) 0.001 (2) 0.0002 (19) 0.005 (2)

C4 0.042 (2) 0.041 (2) 0.047 (2) 0.0007 (19) −0.0031 (19) 0.004 (2)

C5 0.045 (2) 0.034 (2) 0.040 (2) −0.0043 (19) −0.0002 (19) 0.0049 (19)

C6 0.043 (2) 0.033 (2) 0.036 (2) 0.0022 (19) 0.0007 (18) 0.0048 (17)

C7 0.048 (2) 0.038 (2) 0.038 (2) 0.001 (2) 0.0022 (19) 0.0012 (19)

C8 0.064 (4) 0.044 (3) 0.031 (3) 0.000 0.000 −0.002 (3)

O1 0.068 (3) 0.063 (3) 0.056 (3) 0.000 0.000 −0.019 (2)

Geometric parameters (Å, º)

Cl1—C1 1.717 (4) C3—C4 1.382 (6)

Cl2—C2 1.713 (4) C4—C5 1.432 (5)

Cl3—C3 1.724 (4) C5—C6 1.379 (5)

Cl4—C4 1.706 (4) C6—C7 1.398 (5)

C1—C1i 1.392 (8) C6—C6i 1.429 (8)

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supporting information

sup-3 Acta Cryst. (2004). E60, o899–o900

C2—C3 1.413 (6) C8—C7i 1.498 (5)

C1i—C1—C5 122.2 (2) C6—C5—C4 113.8 (4)

C1i—C1—Cl1 117.36 (13) C6—C5—C1 114.5 (3)

C5—C1—Cl1 120.4 (3) C4—C5—C1 131.6 (4)

C7—C2—C3 118.1 (4) C5—C6—C7 127.0 (4)

C7—C2—Cl2 121.1 (3) C5—C6—C6i 123.2 (2)

C3—C2—Cl2 120.8 (3) C7—C6—C6i 109.8 (2)

C4—C3—C2 122.9 (4) C2—C7—C6 118.0 (4)

C4—C3—Cl3 119.8 (3) C2—C7—C8 134.3 (4)

C2—C3—Cl3 117.3 (3) C6—C7—C8 107.7 (4)

C3—C4—C5 120.2 (4) O1—C8—C7 127.5 (2)

C3—C4—Cl4 117.3 (3) O1—C8—C7i 127.5 (2)

C5—C4—Cl4 122.4 (3) C7—C8—C7i 105.0 (5)

References

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