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The odd-alternant perchlorophenalenyl radical, C13Cl9, forms molecular stacks centered on crystallographic threefold rotation axes, but the spacing within the stacks (3.78 Å) is too large to allow good overlap of the orbitals in which the spin density is localized. The radical is ruffled because of the intramolecular repulsions between α Cl atoms (the Cl...Cl peri interactions); the average displacement of an α Cl atom from the molecular plane is ∼0.7 Å. The deviations from molecular planarity do not, however, determine the spacing within the stacks, which is determined instead by interactions between stacks. The modulations found in the P3c1 superstructure are a response to the short interstack contacts that would occur in the average pseudocell structure (R\bar 3m, c′ = c/6). The primary modulation is a pattern of enantiomeric alternation; a secondary modulation involves small rotations of the molecules around their threefold axes. The number (9) of independent molecules in the true cell is exceptionally large because of the conflict between the preference within the molecular stacks for threefold rotational symmetry and the preference in directions perpendicular to the stack axes for twofold alternation of enantiomers. The structural complexity reduces the precision of the distances and angles determined, but the average values found are in excellent agreement with those calculated by density functional theory.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101011193/bs0014sup1.cif
Contains datablocks I, pseudor3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101011193/bs0014Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101011193/bs0014IIsup3.hkl
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768101011193/bs0014sup4.pdf
Supplementary material

Computing details top

For both compounds, data collection: COLLECT software (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) in maXus (Mackay, Gilmore, Edwards, Tremayne, Stewart & Shankland, 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL PC (Sheldrick, 1990).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(I) perchlorophenalenyl radical top
Crystal data top
C13Cl9Melting point: 160_C(dec) in air; 248_C under Ar. K
Mr = 475.18Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3c1Cell parameters from 63143 reflections
a = 18.704 (3) Åθ = 1.3–27.5°
c = 22.675 (4) ŵ = 1.64 mm1
V = 6870 (2) Å3T = 299 K
Z = 18Prisms. The a prism axis is c. The six major faces belong to the form {1 1 -2 0}., black
F(000) = 41580.40 × 0.10 × 0.10 mm
Dx = 2.067 Mg m3
Data collection top
Nonius Kappa-CCD
diffractometer
10524 independent reflections
Radiation source: fine-focus sealed tube6178 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 1.3°
ϕ and ω scans with 1.0° stepsh = 024
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 210
Tmin = 0.79, Tmax = 0.85l = 2929
40131 measured reflections
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)] = 0.094 w = 1/[σ2(Fo2) + (0.03P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.174(Δ/σ)max = 0.001
S = 2.15Δρmax = 0.55 e Å3
10524 reflectionsΔρmin = 0.44 e Å3
448 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
759 restraintsAbsolute structure parameter: 0.25 (9)
Crystal data top
C13Cl9Z = 18
Mr = 475.18Mo Kα radiation
Trigonal, P3c1µ = 1.64 mm1
a = 18.704 (3) ÅT = 299 K
c = 22.675 (4) Å0.40 × 0.10 × 0.10 mm
V = 6870 (2) Å3
Data collection top
Nonius Kappa-CCD
diffractometer
10524 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
6178 reflections with I > 2σ(I)
Tmin = 0.79, Tmax = 0.85Rint = 0.033
40131 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.094759 restraints
wR(F2) = 0.174Δρmax = 0.55 e Å3
S = 2.15Δρmin = 0.44 e Å3
10524 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
448 parametersAbsolute structure parameter: 0.25 (9)
Special details top

Experimental. The crystal-to-detector distance was 40 mm. Each frame was measured for 120 s. The number of scan sets measured was 13; the total number of frames measured was 1475.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl1A0.08999 (11)0.56739 (14)0.25513 (8)0.0547 (5)
Cl2A0.10122 (12)0.41511 (12)0.28623 (9)0.0601 (5)
Cl3A0.26629 (13)0.42849 (10)0.31604 (8)0.0521 (5)
C01A0.1827 (4)0.5774 (4)0.2780 (2)0.0369 (8)
C02A0.1875 (3)0.5071 (3)0.2857 (3)0.0348 (7)
C03A0.2651 (4)0.5157 (3)0.2908 (2)0.0325 (8)
C04A0.3389 (3)0.5920 (3)0.2868 (2)0.0244 (6)
C05A0.33330.66670.2840 (4)0.0240 (5)
Cl1B0.08682 (15)0.55009 (16)0.42405 (11)0.0519 (7)0.7613 (9)
Cl2B0.11564 (15)0.40905 (13)0.45190 (11)0.0531 (7)0.7613 (9)
Cl3B0.28448 (16)0.43259 (14)0.48028 (11)0.0513 (7)0.7613 (9)
C01B0.1854 (5)0.5752 (5)0.4466 (3)0.0369 (8)0.7613 (9)
C02B0.1987 (4)0.5056 (4)0.4542 (3)0.0348 (7)0.7613 (9)
C03B0.2725 (5)0.5134 (4)0.4566 (3)0.0325 (8)0.7613 (9)
C04B0.3464 (4)0.5964 (4)0.4518 (3)0.0244 (6)0.7613 (9)
C05B0.33330.66670.4546 (5)0.0240 (5)0.7613 (9)
Cl1C0.41434 (16)0.90738 (11)0.58813 (8)0.0664 (7)
Cl2C0.57342 (13)0.91056 (13)0.62365 (9)0.0793 (8)
Cl3C0.57568 (12)0.75289 (15)0.64730 (9)0.0762 (7)
C01C0.4115 (4)0.8173 (3)0.6113 (2)0.0335 (8)
C02C0.4810 (3)0.8157 (4)0.6200 (3)0.0419 (8)
C03C0.4861 (4)0.7419 (4)0.6255 (2)0.0340 (8)
C04C0.4102 (3)0.6690 (4)0.6181 (2)0.0353 (7)
C05C0.33330.66670.6187 (4)0.0240 (5)
Cl1D0.77214 (14)0.57785 (11)0.14435 (8)0.0608 (6)
Cl2D0.92106 (12)0.56070 (13)0.17416 (8)0.0592 (6)
Cl3D0.90290 (11)0.39338 (14)0.20401 (8)0.0559 (5)
C01D0.7529 (4)0.4844 (3)0.1677 (3)0.0335 (8)
C02D0.8240 (4)0.4743 (4)0.1746 (3)0.0419 (8)
C03D0.8189 (4)0.3990 (4)0.1818 (2)0.0340 (8)
C04D0.7399 (4)0.3244 (4)0.1757 (2)0.0353 (7)
C05D0.66670.33330.1771 (3)0.0240 (5)
Cl1F0.42632 (11)0.24758 (14)0.47622 (8)0.0580 (6)
Cl2F0.42554 (13)0.08959 (13)0.51044 (8)0.0675 (6)
Cl3F0.58670 (14)0.09276 (10)0.53739 (8)0.0600 (6)
C01F0.5172 (4)0.2591 (4)0.4993 (2)0.0369 (8)
C02F0.5152 (4)0.1797 (3)0.5083 (2)0.0348 (7)
C03F0.5893 (4)0.1853 (3)0.5148 (2)0.0325 (8)
C04F0.6681 (3)0.2579 (3)0.5093 (2)0.0244 (6)
C05F0.66670.33330.5108 (4)0.0240 (5)
Cl1G0.75564 (10)0.11114 (14)0.03330 (8)0.0580 (6)
Cl2G0.77584 (12)0.25933 (12)0.06381 (9)0.0628 (6)
Cl3G0.94543 (14)0.23431 (11)0.09154 (8)0.0591 (6)
C01G0.8511 (4)0.0938 (4)0.0554 (3)0.0369 (8)
C02G0.8607 (3)0.1596 (3)0.0622 (3)0.0348 (7)
C03G0.9431 (4)0.1478 (3)0.0714 (2)0.0325 (8)
C04G1.0108 (3)0.0697 (3)0.0625 (2)0.0244 (6)
C05G1.00000.00000.0632 (4)0.0240 (5)
Cl1H1.07458 (18)0.23985 (15)0.19962 (13)0.0639 (9)0.7613 (9)
Cl2H1.23650 (16)0.24843 (15)0.23517 (11)0.0669 (9)0.7613 (9)
Cl3H1.24226 (15)0.09024 (19)0.25870 (11)0.0680 (9)0.7613 (9)
C01H1.0717 (5)0.1522 (4)0.2207 (3)0.0335 (8)0.7613 (9)
C02H1.1491 (4)0.1557 (4)0.2298 (3)0.0419 (8)0.7613 (9)
C03H1.1520 (5)0.0864 (5)0.2392 (3)0.0340 (8)0.7613 (9)
C04H1.0790 (4)0.0023 (5)0.2307 (3)0.0353 (7)0.7613 (9)
C05H1.00000.00000.2304 (5)0.0240 (5)0.7613 (9)
Cl1J1.09432 (14)0.24303 (11)0.36582 (8)0.0583 (6)
Cl2J1.24842 (13)0.23604 (13)0.39845 (9)0.0651 (6)
Cl3J1.23854 (12)0.07224 (15)0.42688 (8)0.0618 (6)
C01J1.0819 (4)0.1498 (3)0.3897 (3)0.0335 (8)
C02J1.1507 (4)0.1440 (4)0.3962 (3)0.0419 (8)
C03J1.1502 (4)0.0679 (4)0.4071 (2)0.0340 (8)
C04J1.0735 (4)0.0043 (4)0.3949 (2)0.0353 (7)
C05J1.00000.00000.3943 (4)0.0240 (5)
Cl1E0.7885 (3)0.5778 (3)0.3103 (2)0.0550 (14)0.50
Cl2E0.9309 (2)0.5513 (2)0.34349 (17)0.0520 (10)0.50
Cl3E0.8990 (2)0.3786 (2)0.36894 (16)0.0478 (10)0.50
C05E0.66670.33330.3322 (7)0.0240 (5)0.50
C01E0.7647 (3)0.48135 (8)0.3332 (6)0.0335 (8)0.50
C02E0.8294 (2)0.4680 (3)0.3414 (3)0.0419 (8)0.50
C03E0.81388 (15)0.3874 (4)0.3433 (4)0.0340 (8)0.50
C04E0.7339 (2)0.3200 (3)0.3475 (4)0.0353 (7)0.50
Cl4E0.4285 (3)0.2608 (4)0.3118 (2)0.0792 (19)0.50
Cl5E0.4165 (3)0.0985 (3)0.34562 (18)0.0839 (16)0.50
Cl6E0.5711 (3)0.0908 (2)0.37014 (17)0.0788 (16)0.50
C10E0.66670.33330.3402 (7)0.0240 (5)0.50
C06E0.51686 (3)0.2652 (4)0.3372 (6)0.0369 (8)0.50
C07E0.5103 (2)0.1896 (3)0.3446 (4)0.0348 (7)0.50
C08E0.5819 (4)0.18561 (16)0.3516 (4)0.0325 (8)0.50
C09E0.6600 (3)0.25347 (12)0.3411 (4)0.0244 (6)0.50
C10B0.33330.66670.4352 (6)0.0240 (5)0.24
Cl4B0.4089 (4)0.90709 (10)0.4216 (3)0.0664 (7)0.24
Cl5B0.5688 (3)0.9133 (2)0.4570 (3)0.0793 (8)0.24
Cl6B0.5747 (2)0.7563 (4)0.4809 (4)0.0762 (7)0.24
C06B0.4122 (2)0.81614 (4)0.4264 (3)0.0335 (8)0.24
C07B0.48075 (17)0.81952 (15)0.4507 (2)0.0419 (8)0.24
C08B0.47779 (15)0.7463 (2)0.4657 (3)0.0340 (8)0.24
C09B0.40391 (16)0.6709 (2)0.4666 (5)0.0353 (7)0.24
C10H1.00000.00000.2281 (7)0.0240 (5)0.24
Cl4H0.75415 (14)0.1267 (3)0.2015 (4)0.0580 (6)0.24
Cl5H0.7906 (3)0.26427 (13)0.2296 (3)0.0628 (6)0.24
Cl6H0.9656 (4)0.22773 (19)0.2542 (3)0.0591 (6)0.24
C06H0.85268 (5)0.10221 (15)0.2236 (4)0.0369 (8)0.24
C07H0.87040 (16)0.16466 (8)0.2275 (2)0.0348 (7)0.24
C08H0.95210 (19)0.14457 (5)0.2334 (3)0.0325 (8)0.24
C09H1.01744 (12)0.06421 (8)0.2253 (6)0.0244 (6)0.24
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0270 (10)0.0614 (13)0.0707 (12)0.0184 (10)0.0046 (9)0.0034 (10)
Cl2A0.0441 (12)0.0352 (11)0.0754 (13)0.0005 (9)0.0033 (10)0.0010 (10)
Cl3A0.0628 (13)0.0221 (10)0.0663 (12)0.0174 (10)0.0040 (10)0.0077 (8)
C01A0.0367 (19)0.043 (2)0.0277 (17)0.0175 (16)0.0015 (14)0.0060 (14)
C02A0.0320 (18)0.0245 (16)0.0356 (17)0.0050 (14)0.0026 (14)0.0008 (13)
C03A0.047 (2)0.0158 (15)0.0303 (17)0.0127 (15)0.0004 (14)0.0046 (12)
C04A0.0291 (15)0.0201 (15)0.0263 (14)0.0141 (13)0.0011 (12)0.0006 (12)
C05A0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1B0.0369 (14)0.0407 (15)0.0783 (17)0.0196 (12)0.0099 (12)0.0086 (13)
Cl2B0.0476 (16)0.0232 (12)0.0707 (16)0.0043 (12)0.0068 (12)0.0076 (11)
Cl3B0.0582 (17)0.0288 (13)0.0681 (17)0.0225 (13)0.0031 (13)0.0123 (11)
C01B0.0367 (19)0.043 (2)0.0277 (17)0.0175 (16)0.0015 (14)0.0060 (14)
C02B0.0320 (18)0.0245 (16)0.0356 (17)0.0050 (14)0.0026 (14)0.0008 (13)
C03B0.047 (2)0.0158 (15)0.0303 (17)0.0127 (15)0.0004 (14)0.0046 (12)
C04B0.0291 (15)0.0201 (15)0.0263 (14)0.0141 (13)0.0011 (12)0.0006 (12)
C05B0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1C0.115 (2)0.0264 (10)0.0569 (12)0.0350 (12)0.0038 (12)0.0052 (9)
Cl2C0.0467 (13)0.0552 (14)0.0758 (14)0.0198 (10)0.0054 (10)0.0256 (11)
Cl3C0.0394 (13)0.0942 (18)0.0879 (15)0.0280 (13)0.0200 (11)0.0003 (13)
C01C0.0408 (19)0.0157 (15)0.0413 (19)0.0123 (14)0.0080 (14)0.0004 (13)
C02C0.035 (2)0.035 (2)0.0359 (17)0.0026 (15)0.0028 (15)0.0017 (15)
C03C0.0333 (19)0.0354 (19)0.0297 (18)0.0145 (16)0.0028 (14)0.0033 (14)
C04C0.0349 (19)0.0403 (18)0.0297 (15)0.0180 (17)0.0001 (15)0.0006 (13)
C05C0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1D0.0781 (15)0.0340 (11)0.0670 (13)0.0255 (11)0.0052 (11)0.0162 (9)
Cl2D0.0312 (10)0.0440 (12)0.0700 (12)0.0056 (9)0.0058 (9)0.0016 (10)
Cl3D0.0328 (11)0.0687 (15)0.0677 (12)0.0265 (11)0.0082 (9)0.0015 (10)
C01D0.0408 (19)0.0157 (15)0.0413 (19)0.0123 (14)0.0080 (14)0.0004 (13)
C02D0.035 (2)0.035 (2)0.0359 (17)0.0026 (15)0.0028 (15)0.0017 (15)
C03D0.0333 (19)0.0354 (19)0.0297 (18)0.0145 (16)0.0028 (14)0.0033 (14)
C04D0.0349 (19)0.0403 (18)0.0297 (15)0.0180 (17)0.0001 (15)0.0006 (13)
C05D0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1F0.0281 (10)0.0691 (15)0.0696 (13)0.0188 (10)0.0079 (9)0.0010 (10)
Cl2F0.0456 (13)0.0490 (13)0.0728 (14)0.0027 (10)0.0068 (10)0.0096 (10)
Cl3F0.0757 (15)0.0183 (9)0.0739 (14)0.0143 (10)0.0069 (11)0.0079 (9)
C01F0.0367 (19)0.043 (2)0.0277 (17)0.0175 (16)0.0015 (14)0.0060 (14)
C02F0.0320 (18)0.0245 (16)0.0356 (17)0.0050 (14)0.0026 (14)0.0008 (13)
C03F0.047 (2)0.0158 (15)0.0303 (17)0.0127 (15)0.0004 (14)0.0046 (12)
C04F0.0291 (15)0.0201 (15)0.0263 (14)0.0141 (13)0.0011 (12)0.0006 (12)
C05F0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1G0.0213 (10)0.0635 (14)0.0730 (12)0.0090 (9)0.0071 (9)0.0114 (11)
Cl2G0.0474 (12)0.0401 (12)0.0741 (13)0.0017 (10)0.0033 (10)0.0012 (10)
Cl3G0.0813 (16)0.0348 (11)0.0662 (12)0.0326 (11)0.0020 (11)0.0049 (9)
C01G0.0367 (19)0.043 (2)0.0277 (17)0.0175 (16)0.0015 (14)0.0060 (14)
C02G0.0320 (18)0.0245 (16)0.0356 (17)0.0050 (14)0.0026 (14)0.0008 (13)
C03G0.047 (2)0.0158 (15)0.0303 (17)0.0127 (15)0.0004 (14)0.0046 (12)
C04G0.0291 (15)0.0201 (15)0.0263 (14)0.0141 (13)0.0011 (12)0.0006 (12)
C05G0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1H0.088 (2)0.0317 (14)0.0591 (16)0.0201 (14)0.0009 (17)0.0086 (12)
Cl2H0.0563 (18)0.0352 (15)0.0645 (16)0.0106 (13)0.0049 (13)0.0014 (12)
Cl3H0.0272 (14)0.093 (2)0.0750 (19)0.0235 (15)0.0064 (13)0.0068 (15)
C01H0.0408 (19)0.0157 (15)0.0413 (19)0.0123 (14)0.0080 (14)0.0004 (13)
C02H0.035 (2)0.035 (2)0.0359 (17)0.0026 (15)0.0028 (15)0.0017 (15)
C03H0.0333 (19)0.0354 (19)0.0297 (18)0.0145 (16)0.0028 (14)0.0033 (14)
C04H0.0349 (19)0.0403 (18)0.0297 (15)0.0180 (17)0.0001 (15)0.0006 (13)
C05H0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1J0.0773 (15)0.0260 (10)0.0640 (12)0.0200 (10)0.0126 (11)0.0110 (9)
Cl2J0.0397 (12)0.0472 (13)0.0676 (12)0.0089 (9)0.0024 (10)0.0016 (10)
Cl3J0.0469 (12)0.0814 (16)0.0628 (12)0.0365 (12)0.0143 (10)0.0016 (11)
C01J0.0408 (19)0.0157 (15)0.0413 (19)0.0123 (14)0.0080 (14)0.0004 (13)
C02J0.035 (2)0.035 (2)0.0359 (17)0.0026 (15)0.0028 (15)0.0017 (15)
C03J0.0333 (19)0.0354 (19)0.0297 (18)0.0145 (16)0.0028 (14)0.0033 (14)
C04J0.0349 (19)0.0403 (18)0.0297 (15)0.0180 (17)0.0001 (15)0.0006 (13)
C05J0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl1E0.060 (4)0.025 (2)0.073 (3)0.016 (2)0.009 (3)0.0145 (18)
Cl2E0.0204 (17)0.030 (2)0.089 (3)0.0003 (15)0.0002 (17)0.0014 (19)
Cl3E0.030 (2)0.045 (2)0.074 (3)0.0234 (18)0.0015 (17)0.0074 (18)
C05E0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
C01E0.0408 (19)0.0157 (15)0.0413 (19)0.0123 (14)0.0080 (14)0.0004 (13)
C02E0.035 (2)0.035 (2)0.0359 (17)0.0026 (15)0.0028 (15)0.0017 (15)
C03E0.0333 (19)0.0354 (19)0.0297 (18)0.0145 (16)0.0028 (14)0.0033 (14)
C04E0.0349 (19)0.0403 (18)0.0297 (15)0.0180 (17)0.0001 (15)0.0006 (13)
Cl4E0.042 (3)0.137 (6)0.057 (3)0.044 (4)0.008 (2)0.006 (4)
Cl5E0.067 (3)0.063 (3)0.061 (3)0.014 (3)0.016 (2)0.007 (2)
Cl6E0.112 (4)0.021 (2)0.086 (3)0.021 (2)0.016 (3)0.0150 (19)
C10E0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
C06E0.0367 (19)0.043 (2)0.0277 (17)0.0175 (16)0.0015 (14)0.0060 (14)
C07E0.0320 (18)0.0245 (16)0.0356 (17)0.0050 (14)0.0026 (14)0.0008 (13)
C08E0.047 (2)0.0158 (15)0.0303 (17)0.0127 (15)0.0004 (14)0.0046 (12)
C09E0.0291 (15)0.0201 (15)0.0263 (14)0.0141 (13)0.0011 (12)0.0006 (12)
C10B0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl4B0.115 (2)0.0264 (10)0.0569 (12)0.0350 (12)0.0038 (12)0.0052 (9)
Cl5B0.0467 (13)0.0552 (14)0.0758 (14)0.0198 (10)0.0054 (10)0.0256 (11)
Cl6B0.0394 (13)0.0942 (18)0.0879 (15)0.0280 (13)0.0200 (11)0.0003 (13)
C06B0.0408 (19)0.0157 (15)0.0413 (19)0.0123 (14)0.0080 (14)0.0004 (13)
C07B0.035 (2)0.035 (2)0.0359 (17)0.0026 (15)0.0028 (15)0.0017 (15)
C08B0.0333 (19)0.0354 (19)0.0297 (18)0.0145 (16)0.0028 (14)0.0033 (14)
C09B0.0349 (19)0.0403 (18)0.0297 (15)0.0180 (17)0.0001 (15)0.0006 (13)
C10H0.0269 (7)0.0269 (7)0.0183 (11)0.0134 (4)0.0000.000
Cl4H0.0213 (10)0.0635 (14)0.0730 (12)0.0090 (9)0.0071 (9)0.0114 (11)
Cl5H0.0474 (12)0.0401 (12)0.0741 (13)0.0017 (10)0.0033 (10)0.0012 (10)
Cl6H0.0813 (16)0.0348 (11)0.0662 (12)0.0326 (11)0.0020 (11)0.0049 (9)
C06H0.0367 (19)0.043 (2)0.0277 (17)0.0175 (16)0.0015 (14)0.0060 (14)
C07H0.0320 (18)0.0245 (16)0.0356 (17)0.0050 (14)0.0026 (14)0.0008 (13)
C08H0.047 (2)0.0158 (15)0.0303 (17)0.0127 (15)0.0004 (14)0.0046 (12)
C09H0.0291 (15)0.0201 (15)0.0263 (14)0.0141 (13)0.0011 (12)0.0006 (12)
Geometric parameters (Å, º) top
C01A—C02A1.372 (7)C04A—C05A1.452 (5)
C01B—C02B1.452 (9)C04B—C05B1.454 (6)
C01C—C02C1.331 (8)C04C—C05C1.416 (5)
C01D—C02D1.442 (8)C04D—C05D1.461 (6)
C01E—C02E1.367C04E—C05E1.442
C01F—C02F1.481 (7)C04F—C05F1.425 (5)
C01G—C02G1.339 (7)C04G—C05G1.416 (5)
C01H—C02H1.432 (10)C04H—C05H1.456 (7)
C01J—C02J1.354 (8)C04J—C05J1.416 (6)
C06B—C07B1.367C09B—C10B1.467
C06E—C07E1.367C09E—C10E1.436
C06H—C07H1.367C09H—C10H1.394
C01A—C04Ai1.472 (7)Cl1A—C01A1.728 (6)
C01B—C04Bi1.360 (9)Cl1B—C01B1.737 (7)
C01C—C04Cii1.475 (7)Cl1C—C01C1.740 (6)
C01D—C04Diii1.386 (7)Cl1D—C01D1.684 (5)
C01E—C04Eiii1.484Cl1E—C01E1.709
C01F—C04Fiv1.379 (7)Cl1F—C01F1.686 (6)
C01G—C04Gv1.444 (7)Cl1G—C01G1.722 (6)
C01H—C04Hvi1.417 (9)Cl1H—C01H1.682 (7)
C01J—C04Jvi1.407 (7)Cl1J—C01J1.727 (5)
C06B—C09Bii1.801Cl4B—C06B1.736
C06E—C09Eiv1.419Cl4E—C06E1.712
C06H—C09Hv1.441Cl4H—C06H1.736
C02A—C03A1.384 (7)Cl2A—C02A1.669 (6)
C02B—C03B1.315 (9)Cl2B—C02B1.694 (7)
C02C—C03C1.435 (8)Cl2C—C02C1.754 (6)
C02D—C03D1.374 (8)Cl2D—C02D1.724 (6)
C02E—C03E1.386Cl2E—C02E1.753
C02F—C03F1.345 (8)Cl2F—C02F1.682 (6)
C02G—C03G1.460 (8)Cl2G—C02G1.743 (6)
C02H—C03H1.340 (9)Cl2H—C02H1.691 (7)
C02J—C03J1.439 (8)Cl2J—C02J1.778 (6)
C07B—C08B1.386Cl5B—C07B1.709
C07E—C08E1.386Cl5E—C07E1.730
C07H—C08H1.386Cl5H—C07H1.709
C03A—C04A1.408 (7)Cl3A—C03A1.739 (6)
C03B—C04B1.478 (9)Cl3B—C03B1.721 (7)
C03C—C04C1.402 (7)Cl3C—C03C1.658 (6)
C03D—C04D1.444 (7)Cl3D—C03D1.703 (6)
C03E—C04E1.396Cl3E—C03E1.777
C03F—C04F1.425 (7)Cl3F—C03F1.782 (6)
C03G—C04G1.388 (7)Cl3G—C03G1.702 (5)
C03H—C04H1.493 (9)Cl3H—C03H1.712 (8)
C03J—C04J1.422 (7)Cl3J—C03J1.674 (6)
C08B—C09B1.396Cl6B—C08B1.760
C08E—C09E1.396Cl6E—C08E1.733
C08H—C09H1.396Cl6H—C08H1.760
C04Ai—C01A—C02A123.3 (5)C02G—C01G—Cl1G117.5 (5)
C04Bi—C01B—C02B119.9 (7)C02H—C01H—Cl1H117.3 (6)
C04Cii—C01C—C02C120.0 (5)C02J—C01J—Cl1J117.5 (5)
C04Diii—C01D—C02D117.8 (5)C07B—C06B—Cl4B118.2
C04Eiii—C01E—C02E118.8C07E—C06E—Cl4E114.0
C04Fiv—C01F—C02F119.1 (5)C07H—C06H—Cl4H118.2
C04Gv—C01G—C02G121.5 (5)C01A—C02A—Cl2A119.7 (5)
C04Hvi—C01H—C02H118.9 (6)C01B—C02B—Cl2B118.3 (6)
C04Jvi—C01J—C02J118.7 (5)C01C—C02C—Cl2C117.6 (5)
C09Bii—C06B—C07B102.8C01D—C02D—Cl2D119.0 (5)
C09Eiv—C06E—C07E122.4C01E—C02E—Cl2E120.3
C09Hv—C06H—C07H120.1C01F—C02F—Cl2F121.4 (5)
C01A—C02A—C03A117.8 (5)C01G—C02G—Cl2G121.2 (5)
C01B—C02B—C03B123.0 (6)C01H—C02H—Cl2H119.5 (6)
C01C—C02C—C03C124.8 (5)C01J—C02J—Cl2J118.9 (5)
C01D—C02D—C03D123.4 (5)C06B—C07B—Cl5B118.7
C01E—C02E—C03E118.7C06E—C07E—Cl5E122.8
C01F—C02F—C03F115.4 (5)C06H—C07H—Cl5H118.7
C01G—C02G—C03G119.6 (5)C03A—C02A—Cl2A122.4 (5)
C01H—C02H—C03H120.5 (7)C03B—C02B—Cl2B118.2 (6)
C01J—C02J—C03J124.2 (5)C03C—C02C—Cl2C117.6 (5)
C06B—C07B—C08B118.7C03D—C02D—Cl2D117.6 (5)
C06E—C07E—C08E118.7C03E—C02E—Cl2E120.8
C06H—C07H—C08H118.7C03F—C02F—Cl2F123.2 (5)
C02A—C03A—C04A123.5 (5)C03G—C02G—Cl2G119.1 (4)
C02B—C03B—C04B119.6 (6)C03H—C02H—Cl2H119.7 (6)
C02C—C03C—C04C113.7 (5)C03J—C02J—Cl2J116.6 (5)
C02D—C03D—C04D119.6 (6)C08B—C07B—Cl5B122.4
C02E—C03E—C04E122.1C08E—C07E—Cl5E118.5
C02F—C03F—C04F126.8 (5)C08H—C07H—Cl5H122.4
C02G—C03G—C04G118.5 (5)C02A—C03A—Cl3A115.0 (4)
C02H—C03H—C04H122.7 (7)C02B—C03B—Cl3B120.3 (6)
C02J—C03J—C04J114.2 (5)C02C—C03C—Cl3C117.1 (5)
C07B—C08B—C09B122.1C02D—C03D—Cl3D120.3 (5)
C07E—C08E—C09E122.1C02E—C03E—Cl3E113.6
C07H—C08H—C09H122.1C02F—C03F—Cl3F115.4 (4)
C03A—C04A—C05A118.3 (4)C02G—C03G—Cl3G114.9 (4)
C03B—C04B—C05B117.0 (5)C02H—C03H—Cl3H121.0 (6)
C03C—C04C—C05C123.2 (5)C02J—C03J—Cl3J118.6 (5)
C03D—C04D—C05D116.9 (5)C07B—C08B—Cl6B114.4
C03E—C04E—C05E117.4C07E—C08E—Cl6E117.5
C03F—C04F—C05F114.8 (4)C07H—C08H—Cl6H114.3
C03G—C04G—C05G119.5 (4)C04A—C03A—Cl3A120.5 (5)
C03H—C04H—C05H114.3 (6)C04B—C03B—Cl3B118.8 (6)
C03J—C04J—C05J119.7 (5)C04C—C03C—Cl3C128.7 (5)
C08B—C09B—C10B117.2C04D—C03D—Cl3D119.9 (5)
C08E—C09E—C10E117.0C04E—C03E—Cl3E119.9
C08H—C09H—C10H117.7C04F—C03F—Cl3F117.7 (4)
C04Ai—C05A—C04A119.8C04G—C03G—Cl3G126.6 (5)
C04Bi—C05B—C04B119.8C04H—C03H—Cl3H116.2 (6)
C04Cii—C05C—C04C120.0C04J—C03J—Cl3J126.9 (5)
C04Diii—C05D—C04D120.0C09B—C08B—Cl6B123.5
C04Eiii—C05E—C04E114.4C09E—C08E—Cl6E120.3
C04Fiv—C05F—C04F119.9C09H—C08H—Cl6H123.5
C04Gv—C05G—C04G120.0C01Aii—C04A—C03A126.9 (5)
C04Hvi—C05H—C04H120.0C01Bii—C04B—C03B124.0 (6)
C04Jvi—C05J—C04J120.0C01Ci—C04C—C03C121.1 (5)
C09Bii—C10B—C09B98.4C01Div—C04D—C03D123.3 (5)
C09Eiv—C10E—C09E120.0C01Eiv—C04E—C03E120.8
C09Hv—C10H—C09H119.8C01Fiii—C04F—C03F124.5 (5)
C04Ai—C01A—Cl1A118.1 (4)C01Gvi—C04G—C03G122.9 (5)
C04Bi—C01B—Cl1B124.5 (6)C01Hv—C04H—C03H126.5 (7)
C04Cii—C01C—Cl1C119.2 (4)C01Jv—C04J—C03J120.9 (5)
C04Diii—C01D—Cl1D126.0 (5)C06Bi—C09B—C08B115.9
C04Eiii—C01E—Cl1E124.6C06Eiii—C09E—C08E125.9
C04Fiv—C01F—Cl1F127.6 (5)C06Hvi—C09H—C08H122.2
C04Gv—C01G—Cl1G120.9 (4)C01Aii—C04A—C05A114.4 (4)
C04Hvi—C01H—Cl1H123.8 (6)C01Bii—C04B—C05B119.0 (6)
C04Jvi—C01J—Cl1J123.2 (5)C01Ci—C04C—C05C115.6 (5)
C09Bii—C06B—Cl4B116.1C01Div—C04D—C05D119.8 (5)
C09Eiv—C06E—Cl4E122.9C01Eiv—C04E—C05E112.9
C09Hv—C06H—Cl4H120.4C01Fiii—C04F—C05F120.6 (5)
C02A—C01A—Cl1A118.5 (5)C01Gvi—C04G—C05G117.5 (4)
C02B—C01B—Cl1B115.3 (6)C01Hv—C04H—C05H119.1 (6)
C02C—C01C—Cl1C120.7 (5)C01Jv—C04J—C05J119.0 (5)
C02D—C01D—Cl1D115.9 (5)C06Bi—C09B—C10B95.6
C02E—C01E—Cl1E116.6C06Hvi—C09H—C10H119.3
C02F—C01F—Cl1F113.3 (5)C06Eiii—C09E—C10E116.8
Symmetry codes: (i) x+y, x+1, z; (ii) y+1, xy+1, z; (iii) y+1, xy, z; (iv) x+y+1, x+1, z; (v) x+y+2, x+1, z; (vi) y+1, xy1, z.
(pseudor3) perchlorophenalenyl radical top
Crystal data top
C13Cl9Melting point: 160_C(dec) in air; 248_C under Ar. K
Mr = 475.18Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3mCell parameters from 63143 reflections
a = 18.704 (3) Åθ = 1.3–27.5°
c = 3.7792 (7) ŵ = 1.64 mm1
V = 1145.0 (3) Å3T = 299 K
Z = 3Prisms. The a prism axis is c. The six major faces belong to the form {1 1 -2 0}., black
F(000) = 6930.40 × 0.10 × 0.10 mm
Dx = 2.067 Mg m3
Data collection top
Nonius Kappa-CCD
diffractometer
323 independent reflections
Radiation source: fine-focus sealed tube318 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.2°
ϕ and ω scans with 1.0° stepsh = 024
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 210
Tmin = 0.79, Tmax = 0.85l = 44
2409 measured reflections
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullPrimary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.045Secondary atom site location: difference Fourier map
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.03P)2]
where P = (Fo2 + 2Fc2)/3
S = 4.08(Δ/σ)max < 0.001
323 reflectionsΔρmax = 0.36 e Å3
64 parametersΔρmin = 0.33 e Å3
Crystal data top
C13Cl9Z = 3
Mr = 475.18Mo Kα radiation
Trigonal, R3mµ = 1.64 mm1
a = 18.704 (3) ÅT = 299 K
c = 3.7792 (7) Å0.40 × 0.10 × 0.10 mm
V = 1145.0 (3) Å3
Data collection top
Nonius Kappa-CCD
diffractometer
323 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
318 reflections with I > 2σ(I)
Tmin = 0.79, Tmax = 0.85Rint = 0.034
2409 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04564 parameters
wR(F2) = 0.1401 restraint
S = 4.08Δρmax = 0.36 e Å3
323 reflectionsΔρmin = 0.33 e Å3
Special details top

Experimental. The crystal-to-detector distance was 40 mm. Each frame was measured for 120 s. The number of scan sets measured was 13; the total number of frames measured was 1475.

Geometry. The distances and angles are determined for atomic positions averaged over nine independent molecules. The values are reasonably precise but very inaccurate.

Refinement. Friedel reflections were merged during refinement. Refinement with unmerged data gave a Flack parameter of 0.2 (2).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.75782 (16)0.0976 (3)0.1796 (7)0.105 (3)0.50
Cl20.7673 (2)0.2507 (2)0.0146 (12)0.1085 (16)0.50
Cl30.9320 (3)0.23869 (17)0.1771 (7)0.0913 (12)0.50
C010.8507 (4)0.07464 (18)0.0412 (16)0.0575 (18)
C020.8557 (7)0.1564 (5)0.003 (3)0.055 (3)0.50
C030.9368 (8)0.1502 (4)0.044 (2)0.036 (4)0.50
C041.0059 (5)0.0734 (4)0.002 (2)0.0357 (13)0.50
C051.00000.00000.000 (3)0.0271 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0304 (10)0.191 (7)0.0706 (16)0.0397 (16)0.0102 (9)0.0125 (19)
Cl20.086 (2)0.0671 (18)0.0738 (16)0.0352 (14)0.0096 (17)0.0022 (16)
Cl30.160 (3)0.0365 (13)0.0721 (19)0.0450 (16)0.003 (2)0.0086 (12)
C010.027 (2)0.092 (4)0.033 (3)0.0133 (12)0.0033 (19)0.0017 (9)
C020.043 (5)0.049 (5)0.036 (3)0.006 (4)0.001 (3)0.002 (4)
C030.042 (11)0.029 (3)0.038 (3)0.018 (3)0.002 (3)0.006 (2)
C040.048 (3)0.037 (3)0.028 (3)0.025 (3)0.001 (2)0.003 (3)
C050.0293 (18)0.0293 (18)0.023 (3)0.0147 (9)0.0000.000
Geometric parameters (Å, º) top
Cl1—C011.652 (6)C02—C031.470 (15)
Cl2—C021.712 (8)C03—C041.381 (12)
Cl3—C031.688 (9)C04—C051.431 (5)
C01—C021.587 (13)C04—C01i1.307 (9)
C04ii—C01—C02115.0 (6)C02—C03—Cl3114.0 (7)
C04ii—C01—Cl1134.3 (4)C04—C03—Cl3128.4 (10)
C02—C01—Cl1110.1 (5)C03—C04—C05121.1 (8)
C01—C02—C03119.4 (5)C01i—C04—C03114.4 (7)
C01—C02—Cl2120.2 (9)C01i—C04—C05124.5 (6)
C03—C02—Cl2120.4 (8)C04ii—C05—C04120
C02—C03—C04117.4 (8)
Symmetry codes: (i) y+1, xy1, z; (ii) x+y+2, x+1, z.

Experimental details

(I)(pseudor3)
Crystal data
Chemical formulaC13Cl9C13Cl9
Mr475.18475.18
Crystal system, space groupTrigonal, P3c1Trigonal, R3m
Temperature (K)299299
a, c (Å)18.704 (3), 22.675 (4)18.704 (3), 3.7792 (7)
V3)6870 (2)1145.0 (3)
Z183
Radiation typeMo KαMo Kα
µ (mm1)1.641.64
Crystal size (mm)0.40 × 0.10 × 0.100.40 × 0.10 × 0.10
Data collection
DiffractometerNonius Kappa-CCD
diffractometer
Nonius Kappa-CCD
diffractometer
Absorption correctionMulti-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Tmin, Tmax0.79, 0.850.79, 0.85
No. of measured, independent and
observed [I > 2σ(I)] reflections
40131, 10524, 6178 2409, 323, 318
Rint0.0330.034
(sin θ/λ)max1)0.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.094, 0.174, 2.15 0.045, 0.140, 4.08
No. of reflections10524323
No. of parameters44864
No. of restraints7591
Δρmax, Δρmin (e Å3)0.55, 0.440.36, 0.33
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881?
Absolute structure parameter0.25 (9)?

Computer programs: COLLECT software (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) in maXus (Mackay, Gilmore, Edwards, Tremayne, Stewart & Shankland, 1998), SHELXL97 (Sheldrick, 1997), SHELXTL PC (Sheldrick, 1990).

 

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