Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700339X/bt2243sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680700339X/bt2243Isup2.hkl |
CCDC reference: 640267
Key indicators
- Single-crystal X-ray study
- T = 85 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.088
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
C28H18 | F(000) = 744 |
Mr = 354.42 | Dx = 1.275 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9456 reflections |
a = 12.7295 (6) Å | θ = 3.4–26.0° |
b = 8.8187 (3) Å | µ = 0.07 mm−1 |
c = 17.2680 (7) Å | T = 85 K |
β = 107.667 (4)° | Block, colourless |
V = 1847.04 (13) Å3 | 0.45 × 0.40 × 0.20 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer | 2237 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 26.0°, θmin = 3.4° |
ω scans | h = −15→14 |
9456 measured reflections | k = −10→6 |
3548 independent reflections | l = −20→21 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | All H-atom parameters refined |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0477P)2] |
3548 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Experimental. Anthraquinone (41.6 g, 0.20 mol) and tin powder (41.5 g, 0.35 mol) were stirred in boiling acetic acid (350 ml). Concentrated hydrochloric acid (60 ml, 0.70 mol) was added in portions and stirring was continued until all the substrate had dissolved. The mixture was filtered and cooled; the crude product was collected by filtration, dried in vacuum over potassium hydroxide and crystallized from toluene. Anthrone (yield 25.3 g, 75%) was obtained [m.p. 437–439 K (decomposition)]. MS, m/z (int): 194 (100, M+), 180 (5), 16 (2), 165 (85), 152 (8), 139 (7), 82 (17). IR (KBr): 3170, 3140 (aromatic protons); 2920, 2865 (aliphatic protons); 1665 (carbonyl band); 1455 (deformations of methylene group); 720, 710 (deformations of four adjacent protons). 1H NMR (CDCl3): δ 8.27 (dd, 3J = 7.0 Hz, 4J = 2.0 Hz, 2H, 1,8-protons), 7.27–7.52 (m, 6H, remaining aromatic protons), 3.60 (s, 2H, methylene group). The primary mother liquors were diluted with ice and water. An amorphous solid was collected by filtration, dissolved in chloroform and dried over anhydrous magnesium sulfate. The solution was concentrated and cooled to 251 K. The crude product (yield 3.40 g, 9%) looses the solvent at 494–502 K and melts at 590 K. Crystals suitable for X-ray diffraction studies were prepared by slow cooling of the solution in acetic acid; they sublime slowly above 523 K and melt at 589.8 K according to DSC/TGA measurements. MS, m/z (int.); 354 (100, M+), 352 (31), 351 (61), 350 (62), 337 (35), 175 (53), 169 (54). IR (KBr): 3052 (aromatic C—H stretch); 1624, 1519, 1442, 1318 (skeletal vibrations); 732 (out-of-plane hydrogen wag, four adjacent protons). 1H NMR (CDCl3): δ 8.63 (s, 2H, H10), 8.10 (d, 3J = 8.4 Hz, 4H, H1, H-8), 7.39 (m, 4H, H4, H5), 7.10 (m, 8H, H2, H3 and H6, H7). 13C NMR (CDCl3): δ 133.3 (C9), 131.8 (C1A, C8A), 128.7 (C3, C6), 128.5 (C4A, C5A), 127.4 (C10), 127.0 (C2, C7), 126.0 (C4, C5), 125.0 (C1, C8). |
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 | ||
C1 | 0.82648 (12) | 0.39586 (15) | 0.85383 (9) | 0.0291 (4) | |
H1 | 0.8151 (11) | 0.3406 (15) | 0.8016 (8) | 0.035 (4)* | |
C2 | 0.87114 (13) | 0.53756 (16) | 0.86512 (10) | 0.0364 (4) | |
H2 | 0.8972 (12) | 0.5890 (16) | 0.8211 (9) | 0.045 (4)* | |
C3 | 0.88213 (14) | 0.61786 (18) | 0.93804 (10) | 0.0396 (4) | |
H3 | 0.9158 (13) | 0.7211 (19) | 0.9454 (9) | 0.055 (5)* | |
C4 | 0.84919 (13) | 0.55411 (16) | 0.99807 (9) | 0.0346 (4) | |
H4 | 0.8550 (12) | 0.6108 (15) | 1.0503 (9) | 0.038 (4)* | |
C5 | 0.67554 (12) | 0.12931 (18) | 1.10034 (8) | 0.0321 (4) | |
H5 | 0.6820 (11) | 0.1896 (15) | 1.1499 (8) | 0.035 (4)* | |
C6 | 0.63457 (13) | −0.01371 (18) | 1.09214 (9) | 0.0368 (4) | |
H6 | 0.6088 (12) | −0.0630 (15) | 1.1364 (9) | 0.036 (4)* | |
C7 | 0.62817 (13) | −0.09910 (18) | 1.02092 (9) | 0.0333 (4) | |
H7 | 0.5967 (12) | −0.2046 (17) | 1.0150 (9) | 0.044 (4)* | |
C8 | 0.66253 (11) | −0.03853 (16) | 0.96025 (8) | 0.0271 (3) | |
H8 | 0.6551 (11) | −0.0984 (13) | 0.9100 (8) | 0.024 (3)* | |
C9 | 0.74405 (11) | 0.17650 (14) | 0.90496 (7) | 0.0216 (3) | |
C10 | 0.76261 (12) | 0.33990 (16) | 1.04848 (8) | 0.0296 (3) | |
H10 | 0.7704 (11) | 0.3987 (15) | 1.0980 (8) | 0.034 (4)* | |
C4A | 0.80122 (11) | 0.40570 (15) | 0.98907 (8) | 0.0267 (3) | |
C5A | 0.71440 (11) | 0.19642 (16) | 1.03880 (8) | 0.0265 (3) | |
C8A | 0.70660 (11) | 0.11165 (15) | 0.96646 (7) | 0.0222 (3) | |
C1A | 0.78982 (11) | 0.32361 (14) | 0.91512 (8) | 0.0238 (3) | |
C1' | 0.93843 (12) | 0.02967 (15) | 0.88390 (8) | 0.0265 (3) | |
H1' | 0.9446 (11) | 0.0937 (14) | 0.9326 (8) | 0.027 (4)* | |
C2' | 1.02991 (13) | −0.03850 (17) | 0.87514 (9) | 0.0320 (4) | |
H2' | 1.1013 (13) | −0.0255 (16) | 0.9159 (9) | 0.039 (4)* | |
C3' | 1.02261 (13) | −0.13092 (17) | 0.80630 (9) | 0.0328 (4) | |
H3' | 1.0892 (12) | −0.1797 (15) | 0.8015 (8) | 0.032 (4)* | |
C4' | 0.92488 (13) | −0.15006 (15) | 0.74794 (9) | 0.0298 (4) | |
H4' | 0.9212 (11) | −0.2148 (14) | 0.7000 (8) | 0.030 (4)* | |
C5' | 0.53223 (12) | −0.01473 (15) | 0.63044 (8) | 0.0276 (3) | |
H5' | 0.5314 (11) | −0.0760 (14) | 0.5818 (8) | 0.032 (4)* | |
C6' | 0.44353 (13) | 0.06700 (16) | 0.63389 (9) | 0.0296 (4) | |
H6' | 0.3750 (12) | 0.0636 (15) | 0.5903 (9) | 0.035 (4)* | |
C7' | 0.44809 (13) | 0.15428 (16) | 0.70395 (8) | 0.0281 (3) | |
H7' | 0.3808 (13) | 0.2113 (16) | 0.7047 (9) | 0.044 (4)* | |
C8' | 0.54245 (11) | 0.15952 (14) | 0.76777 (8) | 0.0235 (3) | |
H8' | 0.5474 (10) | 0.2256 (14) | 0.8163 (8) | 0.025 (3)* | |
C9' | 0.73822 (11) | 0.08771 (14) | 0.82999 (7) | 0.0208 (3) | |
C10' | 0.72613 (12) | −0.09274 (14) | 0.69280 (8) | 0.0244 (3) | |
H10' | 0.7238 (11) | −0.1555 (14) | 0.6430 (8) | 0.025 (3)* | |
C8A' | 0.63865 (11) | 0.07850 (13) | 0.76617 (7) | 0.0208 (3) | |
C1A' | 0.83360 (11) | 0.01370 (14) | 0.82362 (8) | 0.0227 (3) | |
C5A' | 0.63293 (11) | −0.01261 (14) | 0.69588 (8) | 0.0222 (3) | |
C4A' | 0.82661 (12) | −0.07862 (14) | 0.75364 (8) | 0.0239 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0310 (9) | 0.0269 (8) | 0.0288 (8) | 0.0014 (7) | 0.0081 (7) | 0.0003 (6) |
C2 | 0.0333 (10) | 0.0299 (8) | 0.0449 (10) | −0.0008 (7) | 0.0103 (8) | 0.0041 (7) |
C3 | 0.0346 (10) | 0.0271 (8) | 0.0525 (10) | −0.0027 (7) | 0.0066 (8) | −0.0046 (8) |
C4 | 0.0301 (9) | 0.0287 (8) | 0.0387 (9) | 0.0064 (7) | 0.0012 (7) | −0.0086 (7) |
C5 | 0.0304 (9) | 0.0444 (10) | 0.0222 (8) | 0.0139 (7) | 0.0092 (6) | 0.0031 (7) |
C6 | 0.0366 (10) | 0.0498 (10) | 0.0287 (8) | 0.0113 (8) | 0.0170 (7) | 0.0120 (7) |
C7 | 0.0321 (9) | 0.0368 (9) | 0.0320 (8) | 0.0041 (7) | 0.0114 (7) | 0.0092 (7) |
C8 | 0.0264 (9) | 0.0322 (8) | 0.0225 (7) | 0.0036 (7) | 0.0074 (6) | 0.0028 (6) |
C9 | 0.0201 (8) | 0.0238 (7) | 0.0194 (7) | 0.0054 (6) | 0.0038 (5) | 0.0013 (5) |
C10 | 0.0295 (9) | 0.0349 (8) | 0.0216 (7) | 0.0124 (7) | 0.0037 (6) | −0.0058 (6) |
C4A | 0.0234 (8) | 0.0257 (8) | 0.0276 (7) | 0.0082 (6) | 0.0025 (6) | −0.0024 (6) |
C5A | 0.0228 (8) | 0.0346 (8) | 0.0214 (7) | 0.0123 (6) | 0.0059 (6) | 0.0021 (6) |
C8A | 0.0184 (8) | 0.0278 (7) | 0.0192 (7) | 0.0063 (6) | 0.0042 (5) | 0.0023 (5) |
C1A | 0.0194 (8) | 0.0262 (7) | 0.0237 (7) | 0.0040 (6) | 0.0032 (6) | 0.0006 (6) |
C1' | 0.0292 (9) | 0.0286 (8) | 0.0228 (7) | 0.0057 (7) | 0.0095 (6) | 0.0029 (6) |
C2' | 0.0283 (9) | 0.0398 (9) | 0.0282 (8) | 0.0070 (7) | 0.0090 (7) | 0.0052 (7) |
C3' | 0.0315 (10) | 0.0387 (9) | 0.0330 (8) | 0.0135 (8) | 0.0171 (7) | 0.0085 (7) |
C4' | 0.0394 (10) | 0.0290 (8) | 0.0252 (7) | 0.0084 (7) | 0.0162 (7) | 0.0046 (6) |
C5' | 0.0344 (10) | 0.0234 (7) | 0.0244 (7) | −0.0085 (7) | 0.0079 (6) | −0.0017 (6) |
C6' | 0.0255 (9) | 0.0313 (8) | 0.0281 (8) | −0.0067 (7) | 0.0023 (7) | 0.0036 (6) |
C7' | 0.0247 (9) | 0.0285 (8) | 0.0307 (8) | −0.0011 (7) | 0.0076 (6) | 0.0023 (6) |
C8' | 0.0275 (8) | 0.0199 (7) | 0.0242 (7) | −0.0012 (6) | 0.0095 (6) | 0.0016 (6) |
C9' | 0.0233 (8) | 0.0191 (7) | 0.0210 (7) | −0.0011 (6) | 0.0081 (6) | 0.0024 (5) |
C10' | 0.0356 (9) | 0.0189 (7) | 0.0217 (7) | −0.0015 (6) | 0.0134 (6) | −0.0007 (6) |
C8A' | 0.0244 (8) | 0.0179 (6) | 0.0220 (7) | −0.0022 (6) | 0.0098 (6) | 0.0034 (5) |
C1A' | 0.0273 (8) | 0.0222 (7) | 0.0206 (7) | 0.0015 (6) | 0.0103 (6) | 0.0042 (5) |
C5A' | 0.0283 (8) | 0.0180 (7) | 0.0213 (7) | −0.0052 (6) | 0.0090 (6) | 0.0017 (5) |
C4A' | 0.0327 (9) | 0.0199 (7) | 0.0230 (7) | 0.0025 (6) | 0.0142 (6) | 0.0046 (5) |
C1—C2 | 1.362 (2) | C1'—C2' | 1.3592 (19) |
C1—C1A | 1.4295 (18) | C1'—C1A' | 1.4286 (19) |
C1—H1 | 0.997 (14) | C1'—H1' | 0.996 (13) |
C2—C3 | 1.414 (2) | C2'—C3' | 1.421 (2) |
C2—H2 | 1.024 (15) | C2'—H2' | 0.973 (15) |
C3—C4 | 1.353 (2) | C3'—C4' | 1.353 (2) |
C3—H3 | 0.998 (16) | C3'—H3' | 0.976 (14) |
C4—C4A | 1.433 (2) | C4'—C4A' | 1.4304 (19) |
C4—H4 | 1.015 (14) | C4'—H4' | 0.995 (13) |
C5—C6 | 1.356 (2) | C5'—C6' | 1.356 (2) |
C5—C5A | 1.4294 (19) | C5'—C5A' | 1.4287 (18) |
C5—H5 | 0.990 (14) | C5'—H5' | 0.997 (13) |
C6—C7 | 1.423 (2) | C6'—C7' | 1.420 (2) |
C6—H6 | 1.017 (14) | C6'—H6' | 0.965 (14) |
C7—C8 | 1.3608 (19) | C7'—C8' | 1.3624 (19) |
C7—H7 | 1.006 (15) | C7'—H7' | 0.996 (15) |
C8—C8A | 1.4295 (19) | C8'—C8A' | 1.4253 (19) |
C8—H8 | 0.996 (12) | C8'—H8' | 1.007 (13) |
C9—C8A | 1.4104 (17) | C9'—C8A' | 1.4070 (18) |
C9—C1A | 1.4111 (18) | C9'—C1A' | 1.4118 (18) |
C9—C9' | 1.4954 (17) | C10'—C4A' | 1.393 (2) |
C10—C4A | 1.3917 (19) | C10'—C5A' | 1.3957 (19) |
C10—C5A | 1.394 (2) | C10'—H10' | 1.016 (13) |
C10—H10 | 0.979 (13) | C8A'—C5A' | 1.4389 (17) |
C4A—C1A | 1.4365 (17) | C1A'—C4A' | 1.4373 (17) |
C5A—C8A | 1.4332 (17) | ||
C2—C1—C1A | 121.25 (14) | C2'—C1'—C1A' | 121.18 (13) |
C2—C1—H1 | 121.2 (8) | C2'—C1'—H1' | 119.6 (8) |
C1A—C1—H1 | 117.5 (8) | C1A'—C1'—H1' | 119.2 (8) |
C1—C2—C3 | 120.74 (15) | C1'—C2'—C3' | 120.40 (15) |
C1—C2—H2 | 121.0 (8) | C1'—C2'—H2' | 120.7 (9) |
C3—C2—H2 | 118.2 (8) | C3'—C2'—H2' | 118.9 (9) |
C4—C3—C2 | 120.28 (15) | C4'—C3'—C2' | 120.44 (14) |
C4—C3—H3 | 120.2 (9) | C4'—C3'—H3' | 120.5 (8) |
C2—C3—H3 | 119.5 (9) | C2'—C3'—H3' | 119.1 (8) |
C3—C4—C4 | 121.17 (14) | C3'—C4'—C4A' | 121.29 (14) |
C3—C4—H4 | 121.4 (8) | C3'—C4'—H4' | 119.4 (8) |
C4A—C4—H4 | 117.4 (8) | C4A'—C4'—H4' | 119.3 (8) |
C6—C5—C5A | 121.11 (14) | C6'—C5'—C5A' | 121.16 (14) |
C6—C5—H5 | 121.2 (8) | C6'—C5'—H5' | 122.0 (8) |
C5A—C5—H5 | 117.6 (8) | C5A'—C5'—H5' | 116.8 (8) |
C5—C6—C7 | 120.11 (14) | C5'—C6'—C7' | 120.41 (14) |
C5—C6—H6 | 121.4 (8) | C5'—C6'—H6' | 121.1 (8) |
C7—C6—H6 | 118.5 (8) | C7'—C6'—H6' | 118.4 (8) |
C8—C7—C6 | 120.67 (15) | C8'—C7'—C6' | 120.37 (14) |
C8—C7—H7 | 119.7 (8) | C8'—C7'—H7' | 121.5 (9) |
C6—C7—H7 | 119.6 (8) | C6'—C7'—H7' | 118.1 (9) |
C7—C8—C8 | 121.09 (14) | C7'—C8'—C8A' | 121.27 (13) |
C7—C8—H8 | 119.7 (7) | C7'—C8'—H8' | 120.7 (7) |
C8A—C8—H8 | 119.2 (7) | C8A'—C8'—H8' | 118.0 (7) |
C8A—C9—C1A | 120.03 (12) | C8A'—C9'—C1A' | 120.25 (12) |
C8A—C9—C9' | 120.01 (11) | C8A'—C9'—C9 | 120.30 (12) |
C1A—C9—C9' | 119.94 (11) | C1A'—C9'—C9 | 119.45 (12) |
C4A—C10—C5A | 122.08 (13) | C4A'—C10'—C5A' | 121.52 (12) |
C4A—C10—H10 | 117.3 (8) | C4A'—C10'—H10' | 118.2 (7) |
C5A—C10—H10 | 120.6 (8) | C5A'—C10'—H10' | 120.1 (7) |
C10—C4A—C4 | 122.36 (13) | C9'—C8A'—C8' | 122.06 (12) |
C10—C4A—C1A | 118.83 (13) | C9'—C8A'—C5A' | 119.73 (12) |
C4—C4A—C1A | 118.78 (13) | C8'—C8A'—C5A' | 118.19 (12) |
C10—C5A—C5 | 121.72 (13) | C9'—C1A'—C1' | 122.20 (12) |
C10—C5A—C8A | 119.31 (12) | C9'—C1A'—C4A' | 119.48 (12) |
C5—C5A—C8A | 118.94 (13) | C1'—C1A'—C4A' | 118.30 (12) |
C9—C8A—C8 | 122.27 (12) | C10'—C5A'—C5' | 122.16 (12) |
C9—C8A—C5A | 119.66 (12) | C10'—C5A'—C8A' | 119.26 (13) |
C8—C8A—C5A | 118.06 (12) | C5'—C5A'—C8A' | 118.56 (12) |
C9—C1A—C1 | 122.21 (12) | C10'—C4A'—C4' | 122.06 (12) |
C9—C1A—C4A | 120.02 (12) | C10'—C4A'—C1A' | 119.55 (12) |
C1—C1A—C4A | 117.77 (12) | C4'—C4A'—C1A' | 118.37 (13) |
C1A—C1—C2—C3 | −0.3 (2) | C2'—C3'—C4'—C4A' | 0.0 (2) |
C1—C2—C3—C4 | 0.6 (2) | C5A'—C5'—C6'—C7' | −1.5 (2) |
C2—C3—C4—C4A | −0.9 (2) | C5'—C6'—C7'—C8' | 1.4 (2) |
C5A—C5—C6—C7 | −0.9 (2) | C6'—C7'—C8'—C8A' | 0.1 (2) |
C5—C6—C7—C8 | −0.2 (2) | C8A—C9—C9'—C8A' | 81.08 (16) |
C6—C7—C8—C8A | 0.4 (2) | C1A—C9—C9'—C8A' | −100.66 (15) |
C5A—C10—C4A—C4 | 178.95 (13) | C8A—C9—C9'—C1A' | −99.19 (15) |
C5A—C10—C4A—C1A | 0.7 (2) | C1A—C9—C9'—C1A' | 79.07 (16) |
C3—C4—C4A—C10 | −177.37 (14) | C1A'—C9'—C8A'—C8' | −175.78 (11) |
C3—C4—C4A—C1A | 0.9 (2) | C9—C9'—C8A'—C8' | 3.95 (18) |
C4A—C10—C5A—C5 | 179.62 (13) | C1A'—C9'—C8A'—C5A' | 2.93 (18) |
C4A—C10—C5A—C8A | 1.6 (2) | C9—C9'—C8A'—C5A' | −177.34 (11) |
C6—C5—C5A—C10 | −176.21 (14) | C7'—C8'—C8A'—C9' | 177.23 (12) |
C6—C5—C5A—C8A | 1.8 (2) | C7'—C8'—C8A'—C5A' | −1.50 (18) |
C1A—C9—C8A—C8 | −178.15 (12) | C8A'—C9'—C1A'—C1' | 174.93 (12) |
C9'—C9—C8A—C8 | 0.11 (19) | C9—C9'—C1A'—C1' | −4.80 (18) |
C1A—C9—C8A—C5A | 0.56 (19) | C8A'—C9'—C1A'—C4A' | −3.74 (18) |
C9'—C9—C8A—C5A | 178.82 (12) | C9—C9'—C1A'—C4A' | 176.52 (11) |
C7—C8—C8A—C9 | 179.21 (13) | C2'—C1'—C1A'—C9' | −177.72 (13) |
C7—C8—C8A—C5A | 0.5 (2) | C2'—C1'—C1A'—C4A' | 0.97 (19) |
C10—C5A—C8A—C9 | −2.27 (19) | C4A'—C10'—C5A'—C5' | 173.98 (12) |
C5—C5A—C8A—C9 | 179.68 (12) | C4A'—C10'—C5A'—C8A' | −4.38 (18) |
C10—C5A—C8A—C8 | 176.50 (13) | C6'—C5'—C5A'—C10' | −178.34 (13) |
C5—C5A—C8A—C8 | −1.55 (19) | C6'—C5'—C5A'—C8A' | 0.04 (19) |
C8A—C9—C1A—C1 | −178.44 (13) | C9'—C8A'—C5A'—C10' | 1.10 (17) |
C9'—C9—C1A—C1 | 3.30 (19) | C8'—C8A'—C5A'—C10' | 179.86 (12) |
C8A—C9—C1A—C4A | 1.79 (19) | C9'—C8A'—C5A'—C5' | −177.32 (12) |
C9'—C9—C1A—C4A | −176.47 (12) | C8'—C8A'—C5A'—C5' | 1.43 (17) |
C2—C1—C1A—C9 | −179.54 (13) | C5A'—C10'—C4A'—C4' | −174.67 (12) |
C2—C1—C1A—C4A | 0.2 (2) | C5A'—C10'—C4A'—C1A' | 3.57 (19) |
C10—C4A—C1A—C9 | −2.44 (19) | C3'—C4'—C4A'—C10' | 177.70 (13) |
C4—C4A—C1A—C9 | 179.26 (13) | C3'—C4'—C4A'—C1A' | −0.56 (19) |
C10—C4A—C1A—C1 | 177.78 (13) | C9'—C1A'—C4A'—C10' | 0.54 (18) |
C4—C4A—C1A—C1 | −0.52 (19) | C1'—C1A'—C4A'—C10' | −178.19 (12) |
C1A'—C1'—C2'—C3' | −1.6 (2) | C9'—C1A'—C4A'—C4' | 178.85 (12) |
C1'—C2'—C3'—C4' | 1.2 (2) | C1'—C1A'—C4A'—C4' | 0.12 (17) |