Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010066/ob6051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010066/ob6051Isup2.hkl |
CCDC reference: 146317
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.066
- wR factor = 0.124
- Data-to-parameter ratio = 13.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.489 0.710 Tmin' and Tmax expected: 0.613 0.710 RR' = 0.798 Please check that your absorption correction is appropriate. RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.101
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
An appropriate amount of sodium was placed in a stainless-steel autoclave and the autoclave was filled with carbon tetrachloride up to 75% of the total volume. The autoclave was maintained at 573 K for over 40 h and then allowed to cool to room temperature. A dark solid product was collected and extracted with toluene. The extraction was washed with 1 M HCl and then water. The solution was seperated with neutral Al2O3 column chromatography, using cyclohexane as eluant. The first yellow fraction was collected and analyzed with mass spectra. The molecular peak appears at mass charge ratio of 670. It can be concluded that the molecule contains ten Cl atoms from the chlorine isotope distribution pattern of the molecular peak. Crystals of (I) were obtained from the fraction solution. The melting point is 541 K. The other characterizations of (I): mass spectrum for molecular ion peak, m/z: 670; 1H NMR spectral data (500 MHz, CD3Cl): 7.021, 7.005 (d, aromatic protons, 2H); 6.931, 6.915 (d, aromatic protons, 2H);6.553 (s, methenyl, 1H); 2.202 (s, methyl, 3H).
Data collection: SMART1000 (Bruker, 1998); cell refinement: SMART1000; data reduction: SMART1000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SMART1000; software used to prepare material for publication: SMART1000.
C26H8Cl10 | Dx = 1.803 Mg m−3 |
Mr = 674.82 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 25 reflections |
a = 27.0286 (4) Å | θ = 7.5–15° |
c = 13.6117 (5) Å | µ = 1.14 mm−1 |
V = 9944.0 (4) Å3 | T = 293 K |
Z = 16 | Prism, yellow |
F(000) = 5344 | 0.42 × 0.32 × 0.30 mm |
CCD area-detector diffractometer | 4384 independent reflections |
Radiation source: fine-focus sealed tube | 2147 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.101 |
ω–2θ scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −18→32 |
Tmin = 0.489, Tmax = 0.710 | k = −13→32 |
11159 measured reflections | l = −12→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0278P)2 + 1.2293P] where P = (Fo2 + 2Fc2)/3 |
4384 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C26H8Cl10 | Z = 16 |
Mr = 674.82 | Mo Kα radiation |
Tetragonal, I41/a | µ = 1.14 mm−1 |
a = 27.0286 (4) Å | T = 293 K |
c = 13.6117 (5) Å | 0.42 × 0.32 × 0.30 mm |
V = 9944.0 (4) Å3 |
CCD area-detector diffractometer | 4384 independent reflections |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | 2147 reflections with I > 2σ(I) |
Tmin = 0.489, Tmax = 0.710 | Rint = 0.101 |
11159 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
4384 reflections | Δρmin = −0.32 e Å−3 |
325 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.44280 (6) | 0.77467 (6) | −0.13873 (14) | 0.0593 (5) | |
Cl2 | 0.40668 (6) | 0.77314 (6) | −0.34579 (13) | 0.0574 (5) | |
Cl3 | 0.34681 (7) | 0.71158 (6) | −0.48574 (13) | 0.0625 (5) | |
Cl4 | 0.23640 (6) | 0.69274 (6) | −0.51023 (12) | 0.0584 (5) | |
Cl5 | 0.17302 (5) | 0.66057 (6) | −0.33452 (12) | 0.0488 (5) | |
Cl6 | 0.14928 (6) | 0.65079 (6) | 0.02836 (13) | 0.0508 (5) | |
Cl7 | 0.18900 (6) | 0.67100 (7) | 0.23623 (13) | 0.0637 (5) | |
Cl8 | 0.29831 (7) | 0.69385 (6) | 0.27097 (13) | 0.0666 (6) | |
Cl9 | 0.39512 (7) | 0.65844 (7) | 0.18139 (14) | 0.0752 (6) | |
Cl10 | 0.45723 (6) | 0.69054 (7) | 0.00900 (14) | 0.0660 (6) | |
C1 | 0.3954 (2) | 0.7349 (2) | −0.1695 (5) | 0.0380 (17) | |
C2 | 0.3772 (2) | 0.7357 (2) | −0.2613 (5) | 0.0388 (16) | |
C3 | 0.3106 (2) | 0.70698 (19) | −0.3809 (4) | 0.0373 (16) | |
C4 | 0.2616 (2) | 0.6943 (2) | −0.3944 (4) | 0.0355 (15) | |
C5 | 0.2331 (2) | 0.6795 (2) | −0.3137 (5) | 0.0350 (16) | |
C6 | 0.2242 (2) | 0.65339 (18) | −0.1379 (4) | 0.0296 (14) | |
C7 | 0.2119 (2) | 0.6641 (2) | 0.0435 (5) | 0.0354 (15) | |
C8 | 0.2291 (2) | 0.6723 (2) | 0.1382 (5) | 0.0429 (17) | |
C9 | 0.2794 (2) | 0.6800 (2) | 0.1533 (4) | 0.0421 (17) | |
C10 | 0.3655 (2) | 0.6821 (2) | 0.0790 (5) | 0.0426 (17) | |
C11 | 0.3935 (2) | 0.6962 (2) | 0.0010 (5) | 0.0434 (17) | |
C12 | 0.3715 (2) | 0.7079 (2) | −0.0914 (5) | 0.0333 (15) | |
C13 | 0.3310 (2) | 0.71196 (19) | −0.2853 (4) | 0.0319 (15) | |
C14 | 0.2528 (2) | 0.67773 (19) | −0.2203 (5) | 0.0310 (15) | |
C15 | 0.2421 (2) | 0.66741 (19) | −0.0375 (4) | 0.0322 (15) | |
C16 | 0.3119 (2) | 0.6813 (2) | 0.0728 (5) | 0.0383 (16) | |
C17 | 0.2925 (2) | 0.67929 (19) | −0.0232 (4) | 0.0331 (15) | |
C18 | 0.3220 (2) | 0.69307 (18) | −0.1062 (4) | 0.0307 (15) | |
C19 | 0.3018 (2) | 0.69459 (18) | −0.2052 (4) | 0.0287 (14) | |
C20 | 0.2269 (2) | 0.5971 (2) | −0.1490 (4) | 0.0322 (15) | |
C21 | 0.1845 (2) | 0.5686 (2) | −0.1584 (5) | 0.0467 (18) | |
C22 | 0.1872 (2) | 0.5176 (2) | −0.1676 (5) | 0.0488 (19) | |
C23 | 0.2327 (3) | 0.4936 (2) | −0.1687 (5) | 0.0483 (18) | |
C24 | 0.2745 (2) | 0.5224 (2) | −0.1605 (5) | 0.0498 (18) | |
C25 | 0.2716 (2) | 0.5726 (2) | −0.1500 (4) | 0.0406 (17) | |
C26 | 0.2353 (3) | 0.4378 (2) | −0.1787 (5) | 0.079 (3) | |
H6A | 0.1894 | 0.6634 | −0.1435 | 0.035* | |
H22A | 0.1583 | 0.4992 | −0.1730 | 0.059* | |
H21A | 0.1537 | 0.5839 | −0.1585 | 0.056* | |
H24A | 0.3054 | 0.5073 | −0.1621 | 0.060* | |
H25A | 0.3007 | 0.5908 | −0.1434 | 0.049* | |
H26A | 0.2693 | 0.4275 | −0.1782 | 0.118* | |
H26B | 0.2202 | 0.4280 | −0.2395 | 0.118* | |
H26C | 0.2181 | 0.4227 | −0.1249 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0422 (10) | 0.0609 (12) | 0.0750 (15) | −0.0132 (9) | −0.0051 (9) | 0.0051 (10) |
Cl2 | 0.0592 (11) | 0.0577 (11) | 0.0551 (13) | −0.0102 (9) | 0.0136 (9) | 0.0139 (10) |
Cl3 | 0.0760 (13) | 0.0727 (12) | 0.0387 (12) | −0.0092 (10) | 0.0194 (10) | 0.0008 (10) |
Cl4 | 0.0767 (13) | 0.0668 (12) | 0.0316 (11) | 0.0012 (10) | −0.0079 (9) | 0.0009 (9) |
Cl5 | 0.0407 (10) | 0.0620 (11) | 0.0435 (11) | 0.0056 (8) | −0.0081 (8) | −0.0073 (9) |
Cl6 | 0.0439 (10) | 0.0561 (11) | 0.0525 (12) | −0.0011 (8) | 0.0130 (9) | 0.0079 (9) |
Cl7 | 0.0745 (13) | 0.0764 (13) | 0.0404 (12) | 0.0019 (11) | 0.0241 (10) | 0.0024 (10) |
Cl8 | 0.0931 (15) | 0.0762 (13) | 0.0305 (11) | −0.0084 (11) | 0.0000 (10) | −0.0078 (10) |
Cl9 | 0.0700 (13) | 0.1053 (16) | 0.0503 (14) | 0.0032 (12) | −0.0205 (11) | 0.0156 (12) |
Cl10 | 0.0401 (10) | 0.0869 (14) | 0.0709 (15) | −0.0007 (10) | −0.0141 (10) | 0.0158 (11) |
C1 | 0.028 (4) | 0.035 (4) | 0.051 (5) | 0.001 (3) | 0.001 (3) | −0.001 (3) |
C2 | 0.039 (4) | 0.035 (4) | 0.043 (5) | 0.002 (3) | 0.010 (3) | 0.004 (3) |
C3 | 0.053 (4) | 0.030 (4) | 0.029 (4) | 0.003 (3) | 0.015 (3) | 0.002 (3) |
C4 | 0.054 (4) | 0.034 (4) | 0.018 (4) | 0.006 (3) | −0.002 (3) | 0.000 (3) |
C5 | 0.034 (4) | 0.037 (4) | 0.034 (4) | 0.000 (3) | −0.001 (3) | −0.007 (3) |
C6 | 0.028 (3) | 0.030 (3) | 0.031 (4) | 0.002 (3) | 0.003 (3) | 0.004 (3) |
C7 | 0.038 (4) | 0.030 (4) | 0.038 (5) | 0.000 (3) | 0.006 (3) | −0.001 (3) |
C8 | 0.063 (5) | 0.035 (4) | 0.031 (5) | 0.006 (3) | 0.018 (4) | 0.003 (3) |
C9 | 0.064 (5) | 0.040 (4) | 0.022 (4) | 0.000 (4) | 0.000 (4) | 0.002 (3) |
C10 | 0.051 (5) | 0.043 (4) | 0.033 (5) | −0.001 (3) | −0.015 (4) | −0.001 (3) |
C11 | 0.044 (4) | 0.045 (4) | 0.041 (5) | 0.000 (3) | 0.000 (4) | 0.000 (4) |
C12 | 0.031 (4) | 0.036 (4) | 0.032 (4) | −0.001 (3) | 0.001 (3) | 0.003 (3) |
C13 | 0.040 (4) | 0.027 (3) | 0.029 (4) | 0.002 (3) | 0.007 (3) | −0.001 (3) |
C14 | 0.030 (4) | 0.025 (3) | 0.039 (5) | 0.009 (3) | 0.003 (3) | −0.004 (3) |
C15 | 0.039 (4) | 0.029 (3) | 0.028 (4) | 0.006 (3) | 0.002 (3) | 0.001 (3) |
C16 | 0.054 (4) | 0.033 (4) | 0.028 (4) | −0.003 (3) | −0.005 (4) | 0.000 (3) |
C17 | 0.042 (4) | 0.031 (3) | 0.026 (4) | 0.002 (3) | 0.004 (3) | −0.002 (3) |
C18 | 0.036 (4) | 0.022 (3) | 0.034 (4) | 0.001 (3) | 0.005 (3) | −0.002 (3) |
C19 | 0.036 (4) | 0.023 (3) | 0.027 (4) | 0.005 (3) | 0.008 (3) | 0.002 (3) |
C20 | 0.032 (4) | 0.032 (3) | 0.033 (4) | −0.003 (3) | 0.003 (3) | −0.008 (3) |
C21 | 0.039 (4) | 0.050 (5) | 0.051 (5) | −0.002 (4) | 0.004 (3) | −0.005 (4) |
C22 | 0.047 (5) | 0.052 (5) | 0.048 (5) | −0.029 (4) | 0.004 (4) | −0.007 (4) |
C23 | 0.072 (5) | 0.039 (4) | 0.034 (5) | −0.007 (4) | 0.010 (4) | 0.000 (3) |
C24 | 0.050 (4) | 0.050 (5) | 0.049 (5) | 0.004 (4) | 0.009 (4) | −0.001 (4) |
C25 | 0.042 (4) | 0.035 (4) | 0.044 (5) | −0.002 (3) | 0.004 (3) | −0.003 (3) |
C26 | 0.131 (7) | 0.036 (4) | 0.069 (6) | −0.005 (4) | 0.027 (5) | −0.003 (4) |
Cl1—C1 | 1.725 (6) | C10—C11 | 1.358 (8) |
Cl2—C2 | 1.727 (6) | C10—C16 | 1.450 (8) |
Cl3—C3 | 1.736 (6) | C11—C12 | 1.428 (8) |
Cl4—C4 | 1.718 (6) | C12—C18 | 1.410 (7) |
Cl5—C5 | 1.725 (6) | C13—C19 | 1.426 (7) |
Cl6—C7 | 1.742 (6) | C14—C19 | 1.415 (7) |
Cl7—C8 | 1.720 (6) | C15—C17 | 1.414 (7) |
Cl8—C9 | 1.722 (6) | C16—C17 | 1.410 (8) |
Cl9—C10 | 1.730 (6) | C17—C18 | 1.432 (7) |
Cl10—C11 | 1.732 (6) | C18—C19 | 1.456 (7) |
C1—C2 | 1.343 (8) | C20—C25 | 1.378 (7) |
C1—C12 | 1.441 (8) | C20—C21 | 1.388 (7) |
C2—C13 | 1.441 (7) | C21—C22 | 1.386 (7) |
C3—C4 | 1.379 (7) | C21—H21A | 0.9300 |
C3—C13 | 1.420 (8) | C22—C23 | 1.390 (8) |
C4—C5 | 1.401 (7) | C22—H22A | 0.9300 |
C5—C14 | 1.380 (7) | C23—C24 | 1.376 (8) |
C6—C15 | 1.498 (7) | C23—C26 | 1.515 (7) |
C6—C14 | 1.513 (7) | C24—C25 | 1.367 (7) |
C6—C20 | 1.530 (7) | C24—H24A | 0.9300 |
C6—H6A | 0.9800 | C25—H25A | 0.9300 |
C7—C15 | 1.375 (7) | C26—H26A | 0.9600 |
C7—C8 | 1.388 (8) | C26—H26B | 0.9600 |
C8—C9 | 1.390 (8) | C26—H26C | 0.9600 |
C9—C16 | 1.406 (8) | ||
C2—C1—C12 | 122.0 (5) | C5—C14—C19 | 118.9 (5) |
C2—C1—Cl1 | 119.2 (5) | C5—C14—C6 | 120.1 (5) |
C12—C1—Cl1 | 118.0 (5) | C19—C14—C6 | 120.7 (5) |
C1—C2—C13 | 121.4 (5) | C7—C15—C17 | 118.5 (6) |
C1—C2—Cl2 | 117.4 (5) | C7—C15—C6 | 121.5 (5) |
C13—C2—Cl2 | 120.7 (5) | C17—C15—C6 | 119.7 (5) |
C4—C3—C13 | 121.3 (5) | C9—C16—C17 | 119.2 (6) |
C4—C3—Cl3 | 116.7 (5) | C9—C16—C10 | 125.5 (6) |
C13—C3—Cl3 | 121.8 (5) | C17—C16—C10 | 115.2 (6) |
C3—C4—C5 | 119.7 (5) | C16—C17—C15 | 119.7 (6) |
C3—C4—Cl4 | 120.6 (5) | C16—C17—C18 | 120.9 (5) |
C5—C4—Cl4 | 119.6 (5) | C15—C17—C18 | 119.2 (6) |
C14—C5—C4 | 121.3 (5) | C12—C18—C17 | 119.3 (6) |
C14—C5—Cl5 | 120.3 (5) | C12—C18—C19 | 118.8 (5) |
C4—C5—Cl5 | 118.3 (5) | C17—C18—C19 | 121.8 (5) |
C15—C6—C14 | 113.6 (5) | C14—C19—C13 | 120.9 (6) |
C15—C6—C20 | 109.0 (4) | C14—C19—C18 | 118.5 (5) |
C14—C6—C20 | 109.5 (4) | C13—C19—C18 | 120.5 (5) |
C15—C6—H6A | 108.2 | C25—C20—C21 | 117.2 (5) |
C14—C6—H6A | 108.2 | C25—C20—C6 | 121.4 (5) |
C20—C6—H6A | 108.2 | C21—C20—C6 | 121.4 (5) |
C15—C7—C8 | 122.3 (6) | C22—C21—C20 | 121.1 (5) |
C15—C7—Cl6 | 119.7 (5) | C22—C21—H21A | 119.4 |
C8—C7—Cl6 | 118.0 (5) | C20—C21—H21A | 119.4 |
C7—C8—C9 | 119.3 (6) | C21—C22—C23 | 120.8 (6) |
C7—C8—Cl7 | 120.4 (5) | C21—C22—H22A | 119.6 |
C9—C8—Cl7 | 120.2 (5) | C23—C22—H22A | 119.6 |
C8—C9—C16 | 120.0 (6) | C24—C23—C22 | 117.5 (6) |
C8—C9—Cl8 | 117.5 (5) | C24—C23—C26 | 122.2 (6) |
C16—C9—Cl8 | 122.2 (5) | C22—C23—C26 | 120.4 (6) |
C11—C10—C16 | 121.1 (6) | C25—C24—C23 | 121.6 (6) |
C11—C10—Cl9 | 118.4 (5) | C25—C24—H24A | 119.2 |
C16—C10—Cl9 | 120.2 (5) | C23—C24—H24A | 119.2 |
C10—C11—C12 | 121.2 (6) | C24—C25—C20 | 121.9 (6) |
C10—C11—Cl10 | 118.8 (5) | C24—C25—H25A | 119.1 |
C12—C11—Cl10 | 119.3 (5) | C20—C25—H25A | 119.1 |
C18—C12—C11 | 117.3 (5) | C23—C26—H26A | 109.5 |
C18—C12—C1 | 117.6 (6) | C23—C26—H26B | 109.5 |
C11—C12—C1 | 125.1 (6) | H26A—C26—H26B | 109.5 |
C3—C13—C19 | 117.0 (5) | C23—C26—H26C | 109.5 |
C3—C13—C2 | 125.9 (6) | H26A—C26—H26C | 109.5 |
C19—C13—C2 | 117.0 (6) | H26B—C26—H26C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C26H8Cl10 |
Mr | 674.82 |
Crystal system, space group | Tetragonal, I41/a |
Temperature (K) | 293 |
a, c (Å) | 27.0286 (4), 13.6117 (5) |
V (Å3) | 9944.0 (4) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 1.14 |
Crystal size (mm) | 0.42 × 0.32 × 0.30 |
Data collection | |
Diffractometer | CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Blessing, 1995) |
Tmin, Tmax | 0.489, 0.710 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11159, 4384, 2147 |
Rint | 0.101 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.125, 1.05 |
No. of reflections | 4384 |
No. of parameters | 325 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.32 |
Computer programs: SMART1000 (Bruker, 1998), SMART1000, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
Cl1—C1 | 1.725 (6) | C2—C13 | 1.441 (7) |
Cl2—C2 | 1.727 (6) | C3—C13 | 1.420 (8) |
Cl4—C4 | 1.718 (6) | C6—C15 | 1.498 (7) |
Cl5—C5 | 1.725 (6) | C6—C14 | 1.513 (7) |
Cl6—C7 | 1.742 (6) | C6—C20 | 1.530 (7) |
Cl7—C8 | 1.720 (6) | C11—C12 | 1.428 (8) |
Cl8—C9 | 1.722 (6) | C12—C18 | 1.410 (7) |
Cl9—C10 | 1.730 (6) | C13—C19 | 1.426 (7) |
Cl10—C11 | 1.732 (6) | C17—C18 | 1.432 (7) |
C1—C12 | 1.441 (8) | C18—C19 | 1.456 (7) |
C2—C1—C12 | 122.0 (5) | C14—C6—C20 | 109.5 (4) |
C2—C1—Cl1 | 119.2 (5) | C18—C12—C11 | 117.3 (5) |
C12—C1—Cl1 | 118.0 (5) | C18—C12—C1 | 117.6 (6) |
C1—C2—C13 | 121.4 (5) | C11—C12—C1 | 125.1 (6) |
C1—C2—Cl2 | 117.4 (5) | C5—C14—C19 | 118.9 (5) |
C13—C2—Cl2 | 120.7 (5) | C5—C14—C6 | 120.1 (5) |
C15—C6—C14 | 113.6 (5) | C19—C14—C6 | 120.7 (5) |
C15—C6—C20 | 109.0 (4) |
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In order to explore the formation mechanisms of fullerenes by means of trapping a macro amount of fullerene intermediates during their formation, i.e. fullerene fragment molecules, from a discharge system, several methods, such as discharge in liquid chloroform (Huang et al., 1997), glow discharge (Xie et al., 1998) and microwave discharge (Xie et al., 1999), have been developed in our research group in recent years. Using these approaches, a series of perchlorinated fullerene fragments, such as perchlorofluoanthene, C16Cl10, decachlorocoranulene, C20Cl10, have been obtained. Recently, a new perchlorinated compound, (I), was synthesized by solvothermal reaction, another novel approach developed by our group.
Compound (I) is an interesting molecule as its structure is similar to perchlorobenzofluoanthene, C18Cl10, one of the fullerene fragment molecules. On the other hand, (I) is a potential candidate for the study of non-bonding molecular-orbital properties (Murata et al., 1974), other candidates being 6-methyl-6H-benzo[cd]pyrene, 6-methoxycarbonyl-6H-benzo[cd]pyrene and 6-mesyloxyl-6H-benzo[cd]pyrene (Hara & Yamamoto, 1980), which have been synthesized as parent hydrocarbons of benzo[cd]pyrenyl system.
As shown in Fig. 1, four fused benzo rings are twisted due to the steric repulsion of overcrowded Cl atoms. The tolyl group is almost perpendicular to the skeleton plane of the compound. This perpendicular tail tolyl helps to pack the molecules in the crystals.