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The title compound, C10H10O2, was isolated from Eniconsanthum membranifolium J. Sinclair. There are six independent molecules in the unit cell. Intramolecular hydrogen bonds from the hydroxy H atoms to the carbonyl O atoms are observed in the crystal structure.
Supporting information
CCDC reference: 610755
Key indicators
- Single-crystal X-ray study
- T = 118 K
- Mean (C-C) = 0.011 Å
- R factor = 0.098
- wR factor = 0.211
- Data-to-parameter ratio = 7.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.94
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7F - C8F .. 5.49 su
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 5676
Count of symmetry unique reflns 5756
Completeness (_total/calc) 98.61%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and TEXSAN.
(
R)-(-)-8-Hydroxy-3-methyl-3,4-dihydro-1
H-2-benzopyran-1-one
top
Crystal data top
C10H10O3 | Z = 6 |
Mr = 178.19 | F(000) = 564 |
Triclinic, P1 | Dx = 1.409 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.375 (8) Å | Cell parameters from 2855 reflections |
b = 10.826 (11) Å | θ = 3.0–27.5° |
c = 15.321 (14) Å | µ = 0.10 mm−1 |
α = 70.80 (4)° | T = 118 K |
β = 75.25 (5)° | Block, colourless |
γ = 79.05 (5)° | 0.40 × 0.10 × 0.10 mm |
V = 1260 (2) Å3 | |
Data collection top
Rigaku/MSC Mercury CCD area-detector diffractometer | Rint = 0.061 |
Detector resolution: 14.62 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −10→10 |
10247 measured reflections | k = −12→14 |
5676 independent reflections | l = −19→16 |
4555 reflections with I > 2σ(I) | |
Refinement top
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)] = 0.098 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0535P)2 + 2.6686P] where P = (Fo2 + 2Fc2)/3 |
5676 reflections | (Δ/σ)max = 0.001 |
715 parameters | Δρmax = 0.37 e Å−3 |
3 restraints | Δρmin = −0.36 e Å−3 |
Special details top
Experimental. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 11.0 (1H, s), 7.41 (1H, J
= 8.0 Hz), 6.89 (1H, d, J = 8.0 Hz), 6.69 (1H, d, J = 8.0 Hz),
4.73 (1H, m), 2.93 (2H, d, J = 7.4 Hz), 1.53 (3H, d, J =
6.3 Hz); 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 170.0, 162.3, 139.5, 136.3,
118.0, 116.4, 108.4, 76.9, 34.8, 20.9. |
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 | x | y | z | Uiso*/Ueq | |
C1A | 0.8416 (9) | 0.8257 (7) | 0.7190 (5) | 0.0230 (15) | |
O1A | 0.9527 (6) | 0.8180 (6) | 0.7614 (4) | 0.0307 (12) | |
O2A | 0.6870 (6) | 0.8314 (5) | 0.7666 (4) | 0.0278 (12) | |
C2A | 0.5520 (8) | 0.8722 (8) | 0.7133 (5) | 0.0254 (15) | |
H1A | 0.5481 | 0.9688 | 0.6801 | 0.030* | |
C3A | 0.5797 (9) | 0.7994 (8) | 0.6423 (5) | 0.0262 (16) | |
H2A | 0.4965 | 0.8361 | 0.6018 | 0.031* | |
H3A | 0.5657 | 0.7054 | 0.6750 | 0.031* | |
C4A | 0.7506 (9) | 0.8110 (7) | 0.5825 (5) | 0.0229 (15) | |
C5A | 0.7883 (9) | 0.8047 (8) | 0.4912 (5) | 0.0284 (16) | |
H4A | 0.7032 | 0.7953 | 0.4638 | 0.034* | |
C6A | 0.9500 (10) | 0.8121 (8) | 0.4386 (6) | 0.0302 (17) | |
H5A | 0.9732 | 0.8099 | 0.3751 | 0.036* | |
C7A | 1.0752 (9) | 0.8224 (8) | 0.4762 (5) | 0.0293 (17) | |
H6A | 1.1857 | 0.8244 | 0.4400 | 0.035* | |
C8A | 1.0411 (9) | 0.8299 (7) | 0.5676 (5) | 0.0270 (16) | |
C9A | 0.8769 (8) | 0.8237 (7) | 0.6209 (5) | 0.0205 (14) | |
O3A | 1.1682 (6) | 0.8352 (6) | 0.6049 (4) | 0.0291 (12) | |
H7A | 1.1353 | 0.8235 | 0.6633 | 0.044* | |
C10A | 0.3960 (10) | 0.8459 (8) | 0.7872 (6) | 0.0338 (18) | |
H8A | 0.4028 | 0.7523 | 0.8230 | 0.051* | |
H9A | 0.3003 | 0.8694 | 0.7567 | 0.051* | |
H10A | 0.3830 | 0.8989 | 0.8301 | 0.051* | |
C1B | 0.3221 (9) | 0.4870 (8) | 0.7595 (5) | 0.0276 (16) | |
O1B | 0.3444 (7) | 0.5008 (7) | 0.8314 (4) | 0.0385 (14) | |
O2B | 0.4556 (6) | 0.4714 (5) | 0.6936 (4) | 0.0300 (12) | |
C2B | 0.4391 (8) | 0.4317 (8) | 0.6140 (5) | 0.0254 (16) | |
H1B | 0.4256 | 0.3357 | 0.6360 | 0.031* | |
C3B | 0.2906 (8) | 0.5081 (8) | 0.5766 (5) | 0.0262 (16) | |
H2B | 0.3093 | 0.6019 | 0.5477 | 0.031* | |
H3B | 0.2747 | 0.4749 | 0.5268 | 0.031* | |
C4B | 0.1389 (8) | 0.4972 (7) | 0.6526 (5) | 0.0235 (15) | |
C5B | −0.0175 (8) | 0.4968 (7) | 0.6393 (5) | 0.0227 (15) | |
H4B | −0.0322 | 0.4995 | 0.5792 | 0.027* | |
C6B | −0.1534 (10) | 0.4925 (8) | 0.7137 (7) | 0.0348 (19) | |
H5B | −0.2608 | 0.4928 | 0.7036 | 0.042* | |
C7B | −0.1369 (10) | 0.4878 (7) | 0.8008 (6) | 0.0296 (17) | |
H6B | −0.2320 | 0.4850 | 0.8507 | 0.035* | |
C8B | 0.0212 (9) | 0.4871 (8) | 0.8168 (5) | 0.0262 (16) | |
C9B | 0.1587 (9) | 0.4910 (7) | 0.7420 (5) | 0.0236 (15) | |
O3B | 0.0328 (7) | 0.4861 (6) | 0.9030 (4) | 0.0351 (14) | |
H7B | 0.1286 | 0.5014 | 0.9009 | 0.053* | |
C10B | 0.6019 (8) | 0.4532 (9) | 0.5442 (6) | 0.0302 (18) | |
H8B | 0.6178 | 0.5466 | 0.5241 | 0.045* | |
H9B | 0.6007 | 0.4267 | 0.4891 | 0.045* | |
H10B | 0.6932 | 0.4004 | 0.5741 | 0.045* | |
C1C | 0.9241 (10) | 0.1462 (8) | 0.8723 (5) | 0.0282 (17) | |
O1C | 1.0334 (7) | 0.1312 (6) | 0.9156 (4) | 0.0370 (14) | |
O2C | 0.7649 (6) | 0.1569 (5) | 0.9199 (4) | 0.0273 (11) | |
C2C | 0.6306 (9) | 0.2012 (8) | 0.8681 (5) | 0.0280 (16) | |
H1C | 0.6269 | 0.2982 | 0.8365 | 0.034* | |
C3C | 0.6584 (9) | 0.1304 (8) | 0.7949 (6) | 0.0311 (17) | |
H2C | 0.6476 | 0.0357 | 0.8267 | 0.037* | |
H3C | 0.5727 | 0.1665 | 0.7561 | 0.037* | |
C4C | 0.8276 (9) | 0.1457 (8) | 0.7324 (5) | 0.0271 (16) | |
C5C | 0.8628 (9) | 0.1499 (8) | 0.6380 (5) | 0.0281 (16) | |
H4C | 0.7760 | 0.1476 | 0.6092 | 0.034* | |
C6C | 1.0231 (10) | 0.1574 (8) | 0.5859 (5) | 0.0318 (18) | |
H5C | 1.0461 | 0.1599 | 0.5214 | 0.038* | |
C7C | 1.1503 (10) | 0.1612 (8) | 0.6266 (6) | 0.0334 (18) | |
H6C | 1.2603 | 0.1662 | 0.5899 | 0.040* | |
C8C | 1.1198 (10) | 0.1579 (7) | 0.7197 (6) | 0.0303 (17) | |
C9C | 0.9537 (9) | 0.1524 (7) | 0.7741 (5) | 0.0226 (14) | |
O3C | 1.2467 (6) | 0.1594 (6) | 0.7591 (4) | 0.0334 (13) | |
H7C | 1.2115 | 0.1497 | 0.8171 | 0.050* | |
C10C | 0.4736 (10) | 0.1719 (9) | 0.9418 (6) | 0.040 (2) | |
H8C | 0.4736 | 0.0764 | 0.9693 | 0.060* | |
H9C | 0.3770 | 0.2087 | 0.9125 | 0.060* | |
H10C | 0.4682 | 0.2116 | 0.9916 | 0.060* | |
C1D | 0.7940 (9) | 0.7687 (7) | 0.1912 (5) | 0.0242 (15) | |
O1D | 0.8214 (7) | 0.7741 (6) | 0.2657 (4) | 0.0345 (13) | |
O2D | 0.9274 (6) | 0.7636 (5) | 0.1232 (4) | 0.0262 (11) | |
C2D | 0.9077 (9) | 0.7306 (8) | 0.0392 (5) | 0.0272 (16) | |
H1D | 0.8977 | 0.6344 | 0.0569 | 0.033* | |
C3D | 0.7561 (8) | 0.8088 (8) | 0.0046 (5) | 0.0256 (15) | |
H2D | 0.7376 | 0.7786 | −0.0461 | 0.031* | |
H3D | 0.7731 | 0.9030 | −0.0221 | 0.031* | |
C4D | 0.6054 (9) | 0.7924 (7) | 0.0847 (5) | 0.0240 (15) | |
C5D | 0.4483 (10) | 0.7966 (8) | 0.0706 (6) | 0.0322 (18) | |
H4D | 0.4321 | 0.8056 | 0.0096 | 0.039* | |
C6D | 0.3141 (9) | 0.7878 (9) | 0.1461 (6) | 0.0344 (19) | |
H5D | 0.2054 | 0.7924 | 0.1362 | 0.041* | |
C7D | 0.3355 (9) | 0.7724 (8) | 0.2347 (6) | 0.0297 (17) | |
H6D | 0.2417 | 0.7661 | 0.2855 | 0.036* | |
C8D | 0.4926 (10) | 0.7658 (8) | 0.2510 (5) | 0.0298 (17) | |
C9D | 0.6281 (9) | 0.7740 (7) | 0.1758 (5) | 0.0239 (15) | |
O3D | 0.5076 (7) | 0.7484 (6) | 0.3398 (4) | 0.0348 (13) | |
H7D | 0.6054 | 0.7565 | 0.3396 | 0.052* | |
C10D | 1.0674 (9) | 0.7603 (9) | −0.0298 (6) | 0.0336 (18) | |
H8D | 1.0883 | 0.8496 | −0.0372 | 0.050* | |
H9D | 1.0602 | 0.7538 | −0.0909 | 0.050* | |
H10D | 1.1586 | 0.6969 | −0.0064 | 0.050* | |
C1E | 0.3962 (9) | 0.4345 (7) | 0.3113 (6) | 0.0279 (16) | |
O1E | 0.5069 (6) | 0.4172 (6) | 0.3536 (4) | 0.0308 (12) | |
O2E | 0.2386 (6) | 0.4433 (5) | 0.3591 (4) | 0.0306 (12) | |
C2E | 0.1056 (8) | 0.4906 (8) | 0.3061 (5) | 0.0253 (16) | |
H1E | 0.1074 | 0.5871 | 0.2735 | 0.030* | |
C3E | 0.1316 (8) | 0.4189 (8) | 0.2331 (5) | 0.0242 (15) | |
H2E | 0.1227 | 0.3240 | 0.2649 | 0.029* | |
H3E | 0.0448 | 0.4542 | 0.1949 | 0.029* | |
C4E | 0.2986 (9) | 0.4366 (7) | 0.1706 (5) | 0.0241 (15) | |
C5E | 0.3324 (10) | 0.4480 (8) | 0.0740 (5) | 0.0318 (18) | |
H4E | 0.2466 | 0.4443 | 0.0449 | 0.038* | |
C6E | 0.4920 (9) | 0.4645 (8) | 0.0217 (6) | 0.0304 (18) | |
H5E | 0.5130 | 0.4764 | −0.0443 | 0.037* | |
C7E | 0.6219 (9) | 0.4644 (8) | 0.0622 (6) | 0.0282 (16) | |
H6E | 0.7313 | 0.4729 | 0.0252 | 0.034* | |
C8E | 0.5891 (8) | 0.4516 (7) | 0.1574 (5) | 0.0239 (15) | |
C9E | 0.4286 (9) | 0.4417 (7) | 0.2117 (5) | 0.0235 (15) | |
O3E | 0.7186 (6) | 0.4511 (6) | 0.1963 (4) | 0.0274 (12) | |
H7E | 0.6871 | 0.4326 | 0.2553 | 0.041* | |
C10E | −0.0540 (10) | 0.4686 (8) | 0.3773 (6) | 0.0333 (18) | |
H8E | −0.0507 | 0.3757 | 0.4148 | 0.050* | |
H9E | −0.1470 | 0.4922 | 0.3446 | 0.050* | |
H10E | −0.0690 | 0.5236 | 0.4191 | 0.050* | |
C1F | 0.8426 (9) | 0.1339 (8) | 0.3379 (5) | 0.0274 (16) | |
O1F | 0.8620 (6) | 0.1576 (6) | 0.4066 (4) | 0.0312 (12) | |
O2F | 0.9746 (6) | 0.1292 (6) | 0.2686 (4) | 0.0291 (12) | |
C2F | 0.9683 (9) | 0.0788 (8) | 0.1933 (5) | 0.0265 (16) | |
H1F | 0.9758 | −0.0194 | 0.2174 | 0.032* | |
C3F | 0.8076 (9) | 0.1319 (7) | 0.1588 (5) | 0.0255 (16) | |
H2F | 0.8071 | 0.2273 | 0.1255 | 0.031* | |
H3F | 0.7988 | 0.0871 | 0.1136 | 0.031* | |
C4F | 0.6618 (8) | 0.1098 (7) | 0.2404 (5) | 0.0237 (15) | |
C5F | 0.5110 (9) | 0.0902 (9) | 0.2305 (6) | 0.0332 (18) | |
H4F | 0.4965 | 0.0887 | 0.1714 | 0.040* | |
C6F | 0.3797 (10) | 0.0725 (8) | 0.3088 (6) | 0.0324 (18) | |
H5F | 0.2758 | 0.0574 | 0.3023 | 0.039* | |
C7F | 0.3952 (8) | 0.0761 (7) | 0.3944 (6) | 0.0279 (17) | |
H6F | 0.3034 | 0.0638 | 0.4466 | 0.034* | |
C8F | 0.5469 (10) | 0.0981 (8) | 0.4044 (5) | 0.0315 (18) | |
C9F | 0.6824 (9) | 0.1145 (7) | 0.3274 (5) | 0.0221 (14) | |
O3F | 0.5619 (7) | 0.1072 (6) | 0.4884 (4) | 0.0339 (13) | |
H7F | 0.6522 | 0.1359 | 0.4814 | 0.051* | |
C10F | 1.1203 (9) | 0.1177 (9) | 0.1175 (6) | 0.0349 (19) | |
H8F | 1.1130 | 0.2139 | 0.0927 | 0.052* | |
H9F | 1.1267 | 0.0805 | 0.0662 | 0.052* | |
H10F | 1.2200 | 0.0839 | 0.1444 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.031 (4) | 0.019 (3) | 0.020 (3) | −0.005 (3) | −0.002 (3) | −0.009 (3) |
O1A | 0.029 (3) | 0.038 (3) | 0.028 (3) | 0.001 (2) | −0.010 (2) | −0.013 (2) |
O2A | 0.024 (3) | 0.034 (3) | 0.025 (3) | −0.002 (2) | 0.002 (2) | −0.014 (2) |
C2A | 0.025 (3) | 0.030 (4) | 0.025 (4) | −0.004 (3) | −0.007 (3) | −0.011 (3) |
C3A | 0.019 (3) | 0.038 (4) | 0.021 (4) | −0.005 (3) | 0.001 (3) | −0.011 (3) |
C4A | 0.037 (4) | 0.020 (4) | 0.016 (3) | −0.006 (3) | −0.007 (3) | −0.008 (3) |
C5A | 0.027 (4) | 0.033 (4) | 0.029 (4) | −0.001 (3) | −0.008 (3) | −0.014 (3) |
C6A | 0.035 (4) | 0.026 (4) | 0.024 (4) | −0.001 (3) | 0.002 (3) | −0.007 (3) |
C7A | 0.023 (3) | 0.033 (4) | 0.021 (4) | 0.002 (3) | 0.002 (3) | −0.002 (3) |
C8A | 0.026 (4) | 0.024 (4) | 0.031 (4) | −0.001 (3) | −0.002 (3) | −0.013 (3) |
C9A | 0.024 (3) | 0.024 (3) | 0.017 (3) | −0.005 (3) | −0.006 (3) | −0.007 (3) |
O3A | 0.022 (3) | 0.041 (3) | 0.026 (3) | −0.004 (2) | −0.003 (2) | −0.013 (3) |
C10A | 0.031 (4) | 0.037 (5) | 0.031 (4) | −0.005 (3) | 0.003 (3) | −0.014 (4) |
C1B | 0.026 (4) | 0.037 (4) | 0.019 (4) | −0.008 (3) | 0.001 (3) | −0.009 (3) |
O1B | 0.033 (3) | 0.061 (4) | 0.036 (3) | −0.008 (3) | −0.010 (2) | −0.029 (3) |
O2B | 0.024 (3) | 0.038 (3) | 0.032 (3) | −0.004 (2) | −0.003 (2) | −0.017 (3) |
C2B | 0.022 (3) | 0.037 (4) | 0.018 (3) | −0.001 (3) | 0.003 (3) | −0.016 (3) |
C3B | 0.018 (3) | 0.040 (4) | 0.018 (3) | −0.002 (3) | 0.003 (3) | −0.011 (3) |
C4B | 0.018 (3) | 0.030 (4) | 0.022 (4) | 0.004 (3) | −0.005 (3) | −0.011 (3) |
C5B | 0.019 (3) | 0.025 (4) | 0.025 (4) | −0.006 (3) | −0.003 (3) | −0.009 (3) |
C6B | 0.030 (4) | 0.029 (4) | 0.046 (5) | −0.001 (3) | −0.011 (4) | −0.011 (4) |
C7B | 0.031 (4) | 0.023 (4) | 0.033 (4) | −0.001 (3) | 0.004 (3) | −0.014 (3) |
C8B | 0.023 (4) | 0.046 (5) | 0.013 (3) | −0.005 (3) | −0.004 (3) | −0.013 (3) |
C9B | 0.020 (3) | 0.022 (3) | 0.027 (4) | 0.001 (3) | −0.003 (3) | −0.008 (3) |
O3B | 0.034 (3) | 0.051 (4) | 0.023 (3) | −0.011 (3) | 0.006 (2) | −0.019 (3) |
C10B | 0.011 (3) | 0.055 (5) | 0.028 (4) | −0.007 (3) | 0.001 (3) | −0.018 (4) |
C1C | 0.045 (5) | 0.026 (4) | 0.017 (3) | −0.005 (3) | −0.011 (3) | −0.007 (3) |
O1C | 0.042 (3) | 0.047 (4) | 0.028 (3) | −0.008 (3) | −0.010 (3) | −0.015 (3) |
O2C | 0.028 (3) | 0.034 (3) | 0.022 (3) | −0.002 (2) | −0.006 (2) | −0.011 (2) |
C2C | 0.030 (4) | 0.029 (4) | 0.026 (4) | −0.002 (3) | −0.002 (3) | −0.013 (3) |
C3C | 0.031 (4) | 0.030 (4) | 0.030 (4) | −0.002 (3) | −0.001 (3) | −0.009 (3) |
C4C | 0.022 (4) | 0.033 (4) | 0.026 (4) | 0.000 (3) | −0.005 (3) | −0.012 (3) |
C5C | 0.035 (4) | 0.034 (4) | 0.022 (4) | −0.005 (3) | −0.008 (3) | −0.014 (3) |
C6C | 0.035 (4) | 0.037 (4) | 0.021 (4) | 0.000 (3) | 0.004 (3) | −0.014 (3) |
C7C | 0.032 (4) | 0.041 (5) | 0.029 (4) | −0.001 (3) | −0.001 (3) | −0.018 (4) |
C8C | 0.031 (4) | 0.021 (4) | 0.036 (4) | 0.000 (3) | −0.006 (3) | −0.007 (3) |
C9C | 0.021 (3) | 0.020 (3) | 0.027 (4) | −0.001 (3) | −0.007 (3) | −0.006 (3) |
O3C | 0.023 (3) | 0.034 (3) | 0.042 (3) | −0.001 (2) | −0.007 (2) | −0.011 (3) |
C10C | 0.030 (4) | 0.052 (6) | 0.031 (4) | −0.010 (4) | 0.009 (3) | −0.012 (4) |
C1D | 0.028 (4) | 0.028 (4) | 0.023 (4) | −0.005 (3) | −0.006 (3) | −0.014 (3) |
O1D | 0.037 (3) | 0.040 (3) | 0.028 (3) | −0.003 (3) | −0.009 (2) | −0.011 (3) |
O2D | 0.017 (2) | 0.042 (3) | 0.023 (3) | −0.009 (2) | −0.001 (2) | −0.014 (2) |
C2D | 0.025 (4) | 0.030 (4) | 0.025 (4) | −0.010 (3) | 0.000 (3) | −0.006 (3) |
C3D | 0.018 (3) | 0.033 (4) | 0.024 (4) | −0.007 (3) | 0.000 (3) | −0.006 (3) |
C4D | 0.023 (3) | 0.030 (4) | 0.021 (3) | −0.009 (3) | −0.006 (3) | −0.007 (3) |
C5D | 0.040 (4) | 0.030 (4) | 0.031 (4) | −0.002 (3) | −0.018 (3) | −0.008 (3) |
C6D | 0.018 (4) | 0.048 (5) | 0.037 (5) | 0.002 (3) | 0.000 (3) | −0.019 (4) |
C7D | 0.015 (3) | 0.043 (5) | 0.030 (4) | −0.009 (3) | 0.011 (3) | −0.018 (4) |
C8D | 0.030 (4) | 0.033 (4) | 0.024 (4) | −0.006 (3) | 0.001 (3) | −0.010 (3) |
C9D | 0.027 (4) | 0.027 (4) | 0.015 (3) | −0.005 (3) | −0.001 (3) | −0.004 (3) |
O3D | 0.037 (3) | 0.045 (4) | 0.021 (3) | −0.007 (3) | 0.000 (2) | −0.013 (3) |
C10D | 0.028 (4) | 0.038 (5) | 0.029 (4) | −0.008 (3) | −0.010 (3) | 0.002 (3) |
C1E | 0.032 (4) | 0.022 (4) | 0.030 (4) | −0.005 (3) | −0.005 (3) | −0.009 (3) |
O1E | 0.023 (3) | 0.047 (3) | 0.027 (3) | −0.003 (2) | −0.006 (2) | −0.017 (3) |
O2E | 0.030 (3) | 0.034 (3) | 0.030 (3) | −0.006 (2) | −0.004 (2) | −0.012 (2) |
C2E | 0.017 (3) | 0.032 (4) | 0.022 (4) | −0.007 (3) | 0.003 (3) | −0.004 (3) |
C3E | 0.022 (3) | 0.032 (4) | 0.022 (4) | −0.002 (3) | −0.007 (3) | −0.012 (3) |
C4E | 0.028 (4) | 0.023 (4) | 0.021 (4) | −0.005 (3) | −0.004 (3) | −0.005 (3) |
C5E | 0.031 (4) | 0.043 (5) | 0.021 (4) | −0.005 (3) | 0.001 (3) | −0.015 (4) |
C6E | 0.023 (4) | 0.044 (5) | 0.028 (4) | 0.003 (3) | −0.007 (3) | −0.018 (4) |
C7E | 0.024 (3) | 0.029 (4) | 0.028 (4) | −0.001 (3) | 0.001 (3) | −0.010 (3) |
C8E | 0.017 (3) | 0.032 (4) | 0.023 (4) | −0.003 (3) | 0.002 (3) | −0.013 (3) |
C9E | 0.027 (4) | 0.028 (4) | 0.020 (4) | −0.005 (3) | −0.007 (3) | −0.011 (3) |
O3E | 0.021 (2) | 0.042 (3) | 0.025 (3) | −0.003 (2) | −0.009 (2) | −0.014 (2) |
C10E | 0.038 (5) | 0.028 (4) | 0.027 (4) | −0.001 (3) | −0.002 (3) | −0.005 (3) |
C1F | 0.027 (4) | 0.026 (4) | 0.030 (4) | −0.006 (3) | −0.004 (3) | −0.009 (3) |
O1F | 0.032 (3) | 0.041 (3) | 0.026 (3) | −0.005 (2) | −0.007 (2) | −0.017 (3) |
O2F | 0.023 (3) | 0.038 (3) | 0.026 (3) | −0.008 (2) | −0.003 (2) | −0.007 (2) |
C2F | 0.033 (4) | 0.029 (4) | 0.021 (4) | 0.000 (3) | −0.011 (3) | −0.011 (3) |
C3F | 0.038 (4) | 0.023 (4) | 0.015 (3) | −0.001 (3) | −0.007 (3) | −0.005 (3) |
C4F | 0.016 (3) | 0.029 (4) | 0.028 (4) | −0.005 (3) | 0.001 (3) | −0.014 (3) |
C5F | 0.020 (4) | 0.053 (5) | 0.035 (4) | −0.003 (3) | −0.009 (3) | −0.021 (4) |
C6F | 0.028 (4) | 0.040 (5) | 0.036 (4) | 0.002 (3) | −0.012 (3) | −0.020 (4) |
C7F | 0.014 (3) | 0.031 (4) | 0.032 (4) | −0.005 (3) | 0.005 (3) | −0.007 (3) |
C8F | 0.038 (4) | 0.027 (4) | 0.019 (4) | 0.003 (3) | 0.007 (3) | −0.008 (3) |
C9F | 0.026 (3) | 0.021 (4) | 0.020 (3) | −0.004 (3) | −0.004 (3) | −0.006 (3) |
O3F | 0.031 (3) | 0.051 (4) | 0.022 (3) | −0.006 (3) | 0.002 (2) | −0.019 (3) |
C10F | 0.020 (4) | 0.054 (5) | 0.025 (4) | −0.012 (3) | 0.010 (3) | −0.012 (4) |
Geometric parameters (Å, º) top
C1A—O1A | 1.239 (9) | C1D—O1D | 1.241 (9) |
C1A—O2A | 1.315 (8) | C1D—O2D | 1.327 (8) |
C1A—C9A | 1.463 (9) | C1D—C9D | 1.455 (10) |
O2A—C2A | 1.477 (9) | O2D—C2D | 1.498 (9) |
C2A—C3A | 1.492 (10) | C2D—C10D | 1.493 (10) |
C2A—C10A | 1.498 (10) | C2D—C3D | 1.500 (10) |
C2A—H1A | 1.0000 | C2D—H1D | 1.0000 |
C3A—C4A | 1.493 (10) | C3D—C4D | 1.511 (9) |
C3A—H2A | 0.9900 | C3D—H2D | 0.9900 |
C3A—H3A | 0.9900 | C3D—H3D | 0.9900 |
C4A—C5A | 1.375 (10) | C4D—C5D | 1.376 (10) |
C4A—C9A | 1.382 (10) | C4D—C9D | 1.402 (10) |
C5A—C6A | 1.390 (11) | C5D—C6D | 1.384 (11) |
C5A—H4A | 0.9500 | C5D—H4D | 0.9500 |
C6A—C7A | 1.356 (12) | C6D—C7D | 1.365 (12) |
C6A—H5A | 0.9500 | C6D—H5D | 0.9500 |
C7A—C8A | 1.383 (11) | C7D—C8D | 1.386 (11) |
C7A—H6A | 0.9500 | C7D—H6D | 0.9500 |
C8A—O3A | 1.348 (9) | C8D—O3D | 1.346 (10) |
C8A—C9A | 1.410 (10) | C8D—C9D | 1.388 (9) |
O3A—H7A | 0.8400 | O3D—H7D | 0.8400 |
C10A—H8A | 0.9800 | C10D—H8D | 0.9800 |
C10A—H9A | 0.9800 | C10D—H9D | 0.9800 |
C10A—H10A | 0.9800 | C10D—H10D | 0.9800 |
C1B—O1B | 1.223 (9) | C1E—O1E | 1.215 (9) |
C1B—O2B | 1.328 (8) | C1E—O2E | 1.339 (9) |
C1B—C9B | 1.451 (10) | C1E—C9E | 1.459 (10) |
O2B—C2B | 1.465 (9) | O2E—C2E | 1.460 (9) |
C2B—C3B | 1.490 (10) | C2E—C10E | 1.497 (10) |
C2B—C10B | 1.507 (9) | C2E—C3E | 1.511 (10) |
C2B—H1B | 1.0000 | C2E—H1E | 1.0000 |
C3B—C4B | 1.482 (9) | C3E—C4E | 1.486 (10) |
C3B—H2B | 0.9900 | C3E—H2E | 0.9900 |
C3B—H3B | 0.9900 | C3E—H3E | 0.9900 |
C4B—C5B | 1.377 (10) | C4E—C5E | 1.402 (10) |
C4B—C9B | 1.399 (10) | C4E—C9E | 1.407 (11) |
C5B—C6B | 1.387 (11) | C5E—C6E | 1.383 (10) |
C5B—H4B | 0.9500 | C5E—H4E | 0.9500 |
C6B—C7B | 1.361 (12) | C6E—C7E | 1.383 (11) |
C6B—H5B | 0.9500 | C6E—H5E | 0.9500 |
C7B—C8B | 1.405 (11) | C7E—C8E | 1.378 (11) |
C7B—H6B | 0.9500 | C7E—H6E | 0.9500 |
C8B—O3B | 1.345 (9) | C8E—O3E | 1.363 (9) |
C8B—C9B | 1.399 (9) | C8E—C9E | 1.392 (9) |
O3B—H7B | 0.8400 | O3E—H7E | 0.8400 |
C10B—H8B | 0.9800 | C10E—H8E | 0.9800 |
C10B—H9B | 0.9800 | C10E—H9E | 0.9800 |
C10B—H10B | 0.9800 | C10E—H10E | 0.9800 |
C1C—O1C | 1.219 (10) | C1F—O1F | 1.217 (9) |
C1C—O2C | 1.351 (9) | C1F—O2F | 1.330 (9) |
C1C—C9C | 1.443 (10) | C1F—C9F | 1.452 (10) |
O2C—C2C | 1.458 (9) | O2F—C2F | 1.444 (9) |
C2C—C3C | 1.504 (10) | C2F—C10F | 1.508 (10) |
C2C—C10C | 1.507 (10) | C2F—C3F | 1.514 (10) |
C2C—H1C | 1.0000 | C2F—H1F | 1.0000 |
C3C—C4C | 1.499 (10) | C3F—C4F | 1.499 (10) |
C3C—H2C | 0.9900 | C3F—H2F | 0.9900 |
C3C—H3C | 0.9900 | C3F—H3F | 0.9900 |
C4C—C5C | 1.387 (10) | C4F—C5F | 1.372 (10) |
C4C—C9C | 1.389 (10) | C4F—C9F | 1.406 (10) |
C5C—C6C | 1.378 (10) | C5F—C6F | 1.393 (11) |
C5C—H4C | 0.9500 | C5F—H4F | 0.9500 |
C6C—C7C | 1.378 (12) | C6F—C7F | 1.365 (11) |
C6C—H5C | 0.9500 | C6F—H5F | 0.9500 |
C7C—C8C | 1.374 (11) | C7F—C8F | 1.390 (11) |
C7C—H6C | 0.9500 | C7F—H6F | 0.9500 |
C8C—O3C | 1.354 (10) | C8F—O3F | 1.362 (10) |
C8C—C9C | 1.429 (10) | C8F—C9F | 1.402 (9) |
O3C—H7C | 0.8400 | O3F—H7F | 0.8400 |
C10C—H8C | 0.9800 | C10F—H8F | 0.9800 |
C10C—H9C | 0.9800 | C10F—H9F | 0.9800 |
C10C—H10C | 0.9800 | C10F—H10F | 0.9800 |
| | | |
O1A—C1A—O2A | 117.5 (6) | O1D—C1D—O2D | 115.3 (7) |
O1A—C1A—C9A | 122.7 (7) | O1D—C1D—C9D | 123.5 (7) |
O2A—C1A—C9A | 119.8 (7) | O2D—C1D—C9D | 121.1 (6) |
C1A—O2A—C2A | 118.4 (6) | C1D—O2D—C2D | 117.8 (5) |
O2A—C2A—C3A | 110.8 (6) | C10D—C2D—O2D | 103.4 (6) |
O2A—C2A—C10A | 104.8 (6) | C10D—C2D—C3D | 114.2 (6) |
C3A—C2A—C10A | 113.5 (6) | O2D—C2D—C3D | 110.6 (6) |
O2A—C2A—H1A | 109.2 | C10D—C2D—H1D | 109.5 |
C3A—C2A—H1A | 109.2 | O2D—C2D—H1D | 109.5 |
C10A—C2A—H1A | 109.2 | C3D—C2D—H1D | 109.5 |
C2A—C3A—C4A | 110.1 (6) | C2D—C3D—C4D | 110.4 (6) |
C2A—C3A—H2A | 109.6 | C2D—C3D—H2D | 109.6 |
C4A—C3A—H2A | 109.6 | C4D—C3D—H2D | 109.6 |
C2A—C3A—H3A | 109.6 | C2D—C3D—H3D | 109.6 |
C4A—C3A—H3A | 109.6 | C4D—C3D—H3D | 109.6 |
H2A—C3A—H3A | 108.2 | H2D—C3D—H3D | 108.1 |
C5A—C4A—C9A | 118.6 (7) | C5D—C4D—C9D | 119.6 (7) |
C5A—C4A—C3A | 122.2 (7) | C5D—C4D—C3D | 122.3 (7) |
C9A—C4A—C3A | 119.2 (6) | C9D—C4D—C3D | 118.1 (6) |
C4A—C5A—C6A | 120.5 (7) | C4D—C5D—C6D | 119.5 (8) |
C4A—C5A—H4A | 119.8 | C4D—C5D—H4D | 120.3 |
C6A—C5A—H4A | 119.8 | C6D—C5D—H4D | 120.3 |
C7A—C6A—C5A | 121.3 (7) | C7D—C6D—C5D | 121.1 (7) |
C7A—C6A—H5A | 119.3 | C7D—C6D—H5D | 119.5 |
C5A—C6A—H5A | 119.3 | C5D—C6D—H5D | 119.5 |
C6A—C7A—C8A | 119.6 (7) | C6D—C7D—C8D | 120.6 (6) |
C6A—C7A—H6A | 120.2 | C6D—C7D—H6D | 119.7 |
C8A—C7A—H6A | 120.2 | C8D—C7D—H6D | 119.7 |
O3A—C8A—C7A | 118.7 (7) | O3D—C8D—C7D | 118.4 (7) |
O3A—C8A—C9A | 122.0 (7) | O3D—C8D—C9D | 122.8 (7) |
C7A—C8A—C9A | 119.3 (7) | C7D—C8D—C9D | 118.8 (7) |
C4A—C9A—C8A | 120.7 (7) | C8D—C9D—C4D | 120.5 (7) |
C4A—C9A—C1A | 119.8 (6) | C8D—C9D—C1D | 119.7 (7) |
C8A—C9A—C1A | 119.4 (7) | C4D—C9D—C1D | 119.8 (6) |
C8A—O3A—H7A | 109.5 | C8D—O3D—H7D | 109.5 |
C2A—C10A—H8A | 109.5 | C2D—C10D—H8D | 109.5 |
C2A—C10A—H9A | 109.5 | C2D—C10D—H9D | 109.5 |
H8A—C10A—H9A | 109.5 | H8D—C10D—H9D | 109.5 |
C2A—C10A—H10A | 109.5 | C2D—C10D—H10D | 109.5 |
H8A—C10A—H10A | 109.5 | H8D—C10D—H10D | 109.5 |
H9A—C10A—H10A | 109.5 | H9D—C10D—H10D | 109.5 |
O1B—C1B—O2B | 117.5 (7) | O1E—C1E—O2E | 118.4 (7) |
O1B—C1B—C9B | 123.4 (7) | O1E—C1E—C9E | 122.5 (7) |
O2B—C1B—C9B | 119.1 (7) | O2E—C1E—C9E | 119.0 (7) |
C1B—O2B—C2B | 119.6 (6) | C1E—O2E—C2E | 118.7 (6) |
O2B—C2B—C3B | 110.1 (6) | O2E—C2E—C10E | 106.4 (6) |
O2B—C2B—C10B | 104.9 (6) | O2E—C2E—C3E | 109.7 (6) |
C3B—C2B—C10B | 114.4 (6) | C10E—C2E—C3E | 113.1 (7) |
O2B—C2B—H1B | 109.1 | O2E—C2E—H1E | 109.2 |
C3B—C2B—H1B | 109.1 | C10E—C2E—H1E | 109.2 |
C10B—C2B—H1B | 109.1 | C3E—C2E—H1E | 109.2 |
C4B—C3B—C2B | 111.2 (6) | C4E—C3E—C2E | 109.5 (6) |
C4B—C3B—H2B | 109.4 | C4E—C3E—H2E | 109.8 |
C2B—C3B—H2B | 109.4 | C2E—C3E—H2E | 109.8 |
C4B—C3B—H3B | 109.4 | C4E—C3E—H3E | 109.8 |
C2B—C3B—H3B | 109.4 | C2E—C3E—H3E | 109.8 |
H2B—C3B—H3B | 108.0 | H2E—C3E—H3E | 108.2 |
C5B—C4B—C9B | 119.3 (6) | C5E—C4E—C9E | 119.0 (7) |
C5B—C4B—C3B | 124.0 (7) | C5E—C4E—C3E | 123.5 (7) |
C9B—C4B—C3B | 116.7 (6) | C9E—C4E—C3E | 117.5 (6) |
C4B—C5B—C6B | 119.9 (7) | C6E—C5E—C4E | 119.2 (8) |
C4B—C5B—H4B | 120.1 | C6E—C5E—H4E | 120.4 |
C6B—C5B—H4B | 120.1 | C4E—C5E—H4E | 120.4 |
C7B—C6B—C5B | 121.7 (8) | C7E—C6E—C5E | 122.2 (8) |
C7B—C6B—H5B | 119.2 | C7E—C6E—H5E | 118.9 |
C5B—C6B—H5B | 119.2 | C5E—C6E—H5E | 118.9 |
C6B—C7B—C8B | 119.8 (7) | C8E—C7E—C6E | 118.6 (7) |
C6B—C7B—H6B | 120.1 | C8E—C7E—H6E | 120.7 |
C8B—C7B—H6B | 120.1 | C6E—C7E—H6E | 120.7 |
O3B—C8B—C9B | 122.9 (7) | O3E—C8E—C7E | 117.8 (6) |
O3B—C8B—C7B | 118.3 (6) | O3E—C8E—C9E | 121.0 (6) |
C9B—C8B—C7B | 118.7 (6) | C7E—C8E—C9E | 121.1 (7) |
C4B—C9B—C8B | 120.7 (6) | C8E—C9E—C4E | 119.8 (7) |
C4B—C9B—C1B | 120.9 (6) | C8E—C9E—C1E | 120.0 (6) |
C8B—C9B—C1B | 118.5 (7) | C4E—C9E—C1E | 120.2 (6) |
C8B—O3B—H7B | 109.5 | C8E—O3E—H7E | 109.5 |
C2B—C10B—H8B | 109.5 | C2E—C10E—H8E | 109.5 |
C2B—C10B—H9B | 109.5 | C2E—C10E—H9E | 109.5 |
H8B—C10B—H9B | 109.5 | H8E—C10E—H9E | 109.5 |
C2B—C10B—H10B | 109.5 | C2E—C10E—H10E | 109.5 |
H8B—C10B—H10B | 109.5 | H8E—C10E—H10E | 109.5 |
H9B—C10B—H10B | 109.5 | H9E—C10E—H10E | 109.5 |
O1C—C1C—O2C | 117.6 (7) | O1F—C1F—O2F | 117.8 (7) |
O1C—C1C—C9C | 124.3 (7) | O1F—C1F—C9F | 123.1 (7) |
O2C—C1C—C9C | 118.0 (7) | O2F—C1F—C9F | 119.1 (7) |
C1C—O2C—C2C | 119.7 (6) | C1F—O2F—C2F | 120.7 (6) |
O2C—C2C—C3C | 109.8 (6) | O2F—C2F—C10F | 105.9 (6) |
O2C—C2C—C10C | 105.3 (6) | O2F—C2F—C3F | 110.9 (6) |
C3C—C2C—C10C | 112.8 (7) | C10F—C2F—C3F | 113.0 (6) |
O2C—C2C—H1C | 109.6 | O2F—C2F—H1F | 109.0 |
C3C—C2C—H1C | 109.6 | C10F—C2F—H1F | 109.0 |
C10C—C2C—H1C | 109.6 | C3F—C2F—H1F | 109.0 |
C4C—C3C—C2C | 110.7 (7) | C4F—C3F—C2F | 110.3 (6) |
C4C—C3C—H2C | 109.5 | C4F—C3F—H2F | 109.6 |
C2C—C3C—H2C | 109.5 | C2F—C3F—H2F | 109.6 |
C4C—C3C—H3C | 109.5 | C4F—C3F—H3F | 109.6 |
C2C—C3C—H3C | 109.5 | C2F—C3F—H3F | 109.6 |
H2C—C3C—H3C | 108.1 | H2F—C3F—H3F | 108.1 |
C5C—C4C—C9C | 119.9 (7) | C5F—C4F—C9F | 120.6 (7) |
C5C—C4C—C3C | 123.4 (7) | C5F—C4F—C3F | 121.7 (7) |
C9C—C4C—C3C | 116.7 (7) | C9F—C4F—C3F | 117.7 (6) |
C6C—C5C—C4C | 120.3 (7) | C4F—C5F—C6F | 118.8 (7) |
C6C—C5C—H4C | 119.8 | C4F—C5F—H4F | 120.6 |
C4C—C5C—H4C | 119.8 | C6F—C5F—H4F | 120.6 |
C7C—C6C—C5C | 120.6 (7) | C7F—C6F—C5F | 122.2 (7) |
C7C—C6C—H5C | 119.7 | C7F—C6F—H5F | 118.9 |
C5C—C6C—H5C | 119.7 | C5F—C6F—H5F | 118.9 |
C8C—C7C—C6C | 120.7 (8) | C6F—C7F—C8F | 119.1 (7) |
C8C—C7C—H6C | 119.7 | C6F—C7F—H6F | 120.4 |
C6C—C7C—H6C | 119.7 | C8F—C7F—H6F | 120.4 |
O3C—C8C—C7C | 119.9 (7) | O3F—C8F—C7F | 119.6 (7) |
O3C—C8C—C9C | 120.7 (7) | O3F—C8F—C9F | 120.2 (8) |
C7C—C8C—C9C | 119.3 (8) | C7F—C8F—C9F | 120.1 (7) |
C4C—C9C—C8C | 119.2 (7) | C8F—C9F—C4F | 119.0 (7) |
C4C—C9C—C1C | 122.1 (7) | C8F—C9F—C1F | 120.5 (7) |
C8C—C9C—C1C | 118.7 (7) | C4F—C9F—C1F | 120.4 (6) |
C8C—O3C—H7C | 109.5 | C8F—O3F—H7F | 109.5 |
C2C—C10C—H8C | 109.5 | C2F—C10F—H8F | 109.5 |
C2C—C10C—H9C | 109.5 | C2F—C10F—H9F | 109.5 |
H8C—C10C—H9C | 109.5 | H8F—C10F—H9F | 109.5 |
C2C—C10C—H10C | 109.5 | C2F—C10F—H10F | 109.5 |
H8C—C10C—H10C | 109.5 | H8F—C10F—H10F | 109.5 |
H9C—C10C—H10C | 109.5 | H9F—C10F—H10F | 109.5 |
| | | |
O1A—C1A—O2A—C2A | 165.6 (6) | O1D—C1D—O2D—C2D | 168.3 (6) |
C9A—C1A—O2A—C2A | −16.7 (9) | C9D—C1D—O2D—C2D | −14.6 (10) |
C1A—O2A—C2A—C3A | 47.7 (8) | C1D—O2D—C2D—C10D | 168.8 (6) |
C1A—O2A—C2A—C10A | 170.5 (6) | C1D—O2D—C2D—C3D | 46.2 (8) |
O2A—C2A—C3A—C4A | −52.0 (8) | C10D—C2D—C3D—C4D | −168.9 (7) |
C10A—C2A—C3A—C4A | −169.6 (7) | O2D—C2D—C3D—C4D | −52.8 (8) |
C2A—C3A—C4A—C5A | −152.1 (7) | C2D—C3D—C4D—C5D | −148.6 (8) |
C2A—C3A—C4A—C9A | 30.3 (10) | C2D—C3D—C4D—C9D | 32.3 (10) |
C9A—C4A—C5A—C6A | −0.5 (11) | C9D—C4D—C5D—C6D | 2.4 (12) |
C3A—C4A—C5A—C6A | −178.1 (7) | C3D—C4D—C5D—C6D | −176.7 (8) |
C4A—C5A—C6A—C7A | 1.6 (12) | C4D—C5D—C6D—C7D | −1.2 (13) |
C5A—C6A—C7A—C8A | −2.1 (12) | C5D—C6D—C7D—C8D | 0.3 (13) |
C6A—C7A—C8A—O3A | 177.6 (7) | C6D—C7D—C8D—O3D | −178.9 (8) |
C6A—C7A—C8A—C9A | 1.4 (11) | C6D—C7D—C8D—C9D | −0.5 (12) |
C5A—C4A—C9A—C8A | −0.1 (11) | O3D—C8D—C9D—C4D | −179.9 (7) |
C3A—C4A—C9A—C8A | 177.6 (7) | C7D—C8D—C9D—C4D | 1.7 (12) |
C5A—C4A—C9A—C1A | −177.8 (7) | O3D—C8D—C9D—C1D | −2.3 (12) |
C3A—C4A—C9A—C1A | 0.0 (11) | C7D—C8D—C9D—C1D | 179.4 (7) |
O3A—C8A—C9A—C4A | −176.4 (7) | C5D—C4D—C9D—C8D | −2.7 (12) |
C7A—C8A—C9A—C4A | −0.3 (11) | C3D—C4D—C9D—C8D | 176.4 (7) |
O3A—C8A—C9A—C1A | 1.3 (11) | C5D—C4D—C9D—C1D | 179.6 (7) |
C7A—C8A—C9A—C1A | 177.3 (7) | C3D—C4D—C9D—C1D | −1.2 (11) |
O1A—C1A—C9A—C4A | 169.5 (7) | O1D—C1D—C9D—C8D | −9.7 (12) |
O2A—C1A—C9A—C4A | −8.1 (10) | O2D—C1D—C9D—C8D | 173.5 (7) |
O1A—C1A—C9A—C8A | −8.2 (11) | O1D—C1D—C9D—C4D | 168.0 (7) |
O2A—C1A—C9A—C8A | 174.2 (6) | O2D—C1D—C9D—C4D | −8.9 (11) |
O1B—C1B—O2B—C2B | 169.3 (7) | O1E—C1E—O2E—C2E | 167.6 (7) |
C9B—C1B—O2B—C2B | −12.5 (10) | C9E—C1E—O2E—C2E | −14.4 (10) |
C1B—O2B—C2B—C3B | 44.2 (9) | C1E—O2E—C2E—C10E | 170.8 (6) |
C1B—O2B—C2B—C10B | 167.7 (7) | C1E—O2E—C2E—C3E | 48.1 (8) |
O2B—C2B—C3B—C4B | −53.9 (8) | O2E—C2E—C3E—C4E | −56.5 (8) |
C10B—C2B—C3B—C4B | −171.7 (7) | C10E—C2E—C3E—C4E | −175.1 (7) |
C2B—C3B—C4B—C5B | −146.6 (8) | C2E—C3E—C4E—C5E | −145.0 (7) |
C2B—C3B—C4B—C9B | 35.4 (10) | C2E—C3E—C4E—C9E | 35.1 (9) |
C9B—C4B—C5B—C6B | 1.1 (11) | C9E—C4E—C5E—C6E | −0.3 (12) |
C3B—C4B—C5B—C6B | −176.9 (7) | C3E—C4E—C5E—C6E | 179.8 (8) |
C4B—C5B—C6B—C7B | −0.4 (12) | C4E—C5E—C6E—C7E | 3.0 (13) |
C5B—C6B—C7B—C8B | −0.1 (12) | C5E—C6E—C7E—C8E | −2.2 (12) |
C6B—C7B—C8B—O3B | 178.2 (8) | C6E—C7E—C8E—O3E | 179.8 (7) |
C6B—C7B—C8B—C9B | −0.1 (12) | C6E—C7E—C8E—C9E | −1.3 (12) |
C5B—C4B—C9B—C8B | −1.3 (11) | O3E—C8E—C9E—C4E | −177.2 (7) |
C3B—C4B—C9B—C8B | 176.8 (7) | C7E—C8E—C9E—C4E | 3.9 (12) |
C5B—C4B—C9B—C1B | 178.1 (7) | O3E—C8E—C9E—C1E | 1.8 (11) |
C3B—C4B—C9B—C1B | −3.8 (11) | C7E—C8E—C9E—C1E | −177.1 (7) |
O3B—C8B—C9B—C4B | −177.4 (7) | C5E—C4E—C9E—C8E | −3.0 (11) |
C7B—C8B—C9B—C4B | 0.8 (11) | C3E—C4E—C9E—C8E | 176.8 (7) |
O3B—C8B—C9B—C1B | 3.2 (12) | C5E—C4E—C9E—C1E | 178.0 (7) |
C7B—C8B—C9B—C1B | −178.5 (7) | C3E—C4E—C9E—C1E | −2.2 (11) |
O1B—C1B—C9B—C4B | 169.0 (8) | O1E—C1E—C9E—C8E | −11.1 (12) |
O2B—C1B—C9B—C4B | −9.0 (11) | O2E—C1E—C9E—C8E | 170.9 (7) |
O1B—C1B—C9B—C8B | −11.6 (12) | O1E—C1E—C9E—C4E | 167.9 (7) |
O2B—C1B—C9B—C8B | 170.4 (7) | O2E—C1E—C9E—C4E | −10.1 (11) |
O1C—C1C—O2C—C2C | 167.6 (7) | O1F—C1F—O2F—C2F | 168.8 (7) |
C9C—C1C—O2C—C2C | −12.7 (10) | C9F—C1F—O2F—C2F | −12.9 (10) |
C1C—O2C—C2C—C3C | 45.6 (9) | C1F—O2F—C2F—C10F | 166.9 (7) |
C1C—O2C—C2C—C10C | 167.3 (6) | C1F—O2F—C2F—C3F | 43.9 (9) |
O2C—C2C—C3C—C4C | −54.1 (8) | O2F—C2F—C3F—C4F | −51.6 (8) |
C10C—C2C—C3C—C4C | −171.2 (7) | C10F—C2F—C3F—C4F | −170.4 (7) |
C2C—C3C—C4C—C5C | −148.3 (8) | C2F—C3F—C4F—C5F | −149.4 (7) |
C2C—C3C—C4C—C9C | 33.4 (10) | C2F—C3F—C4F—C9F | 32.9 (9) |
C9C—C4C—C5C—C6C | 1.6 (12) | C9F—C4F—C5F—C6F | −1.2 (12) |
C3C—C4C—C5C—C6C | −176.7 (8) | C3F—C4F—C5F—C6F | −178.9 (8) |
C4C—C5C—C6C—C7C | −0.2 (12) | C4F—C5F—C6F—C7F | 1.1 (13) |
C5C—C6C—C7C—C8C | −0.1 (13) | C5F—C6F—C7F—C8F | 0.0 (12) |
C6C—C7C—C8C—O3C | 178.8 (7) | C6F—C7F—C8F—O3F | 177.4 (7) |
C6C—C7C—C8C—C9C | −0.9 (12) | C6F—C7F—C8F—C9F | −0.8 (11) |
C5C—C4C—C9C—C8C | −2.6 (11) | O3F—C8F—C9F—C4F | −177.5 (7) |
C3C—C4C—C9C—C8C | 175.8 (7) | C7F—C8F—C9F—C4F | 0.7 (11) |
C5C—C4C—C9C—C1C | −178.9 (7) | O3F—C8F—C9F—C1F | 3.5 (11) |
C3C—C4C—C9C—C1C | −0.6 (11) | C7F—C8F—C9F—C1F | −178.3 (7) |
O3C—C8C—C9C—C4C | −177.4 (7) | C5F—C4F—C9F—C8F | 0.4 (11) |
C7C—C8C—C9C—C4C | 2.3 (11) | C3F—C4F—C9F—C8F | 178.2 (7) |
O3C—C8C—C9C—C1C | −1.0 (11) | C5F—C4F—C9F—C1F | 179.3 (7) |
C7C—C8C—C9C—C1C | 178.7 (7) | C3F—C4F—C9F—C1F | −2.9 (10) |
O1C—C1C—C9C—C4C | 168.1 (8) | O1F—C1F—C9F—C8F | −11.9 (12) |
O2C—C1C—C9C—C4C | −11.5 (11) | O2F—C1F—C9F—C8F | 169.9 (7) |
O1C—C1C—C9C—C8C | −8.2 (11) | O1F—C1F—C9F—C4F | 169.1 (8) |
O2C—C1C—C9C—C8C | 172.2 (7) | O2F—C1F—C9F—C4F | −9.1 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H7A···O1A | 0.84 | 1.85 | 2.583 (8) | 146 |
O3B—H7B···O1B | 0.84 | 1.85 | 2.574 (8) | 144 |
O3C—H7C···O1C | 0.84 | 1.82 | 2.564 (8) | 147 |
O3D—H7D···O1D | 0.84 | 1.88 | 2.612 (8) | 145 |
O3E—H7E···O1E | 0.84 | 1.83 | 2.564 (8) | 145 |
O3F—H7F···O1F | 0.84 | 1.85 | 2.579 (8) | 145 |
C2B—H1B···O3Ci | 1.00 | 2.59 | 3.450 (11) | 144 |
C2F—H1F···O1Dii | 1.00 | 2.60 | 3.474 (11) | 147 |
C3C—H2C···O2Aii | 0.99 | 2.60 | 3.362 (10) | 134 |
C3D—H3D···O2Ciii | 0.99 | 2.59 | 3.569 (10) | 170 |
C6A—H5A···O1D | 0.95 | 2.51 | 3.269 (11) | 138 |
C6B—H5B···O2Bi | 0.95 | 2.48 | 3.422 (10) | 173 |
C6D—H5D···O2Di | 0.95 | 2.47 | 3.412 (10) | 170 |
C6E—H5E···O1Biv | 0.95 | 2.57 | 3.328 (10) | 137 |
C10D—H9D···O1Aiv | 0.98 | 2.49 | 3.402 (10) | 156 |
C10B—H9B···O1E | 0.98 | 2.44 | 3.371 (10) | 159 |
C10F—H9F···O1Civ | 0.98 | 2.48 | 3.306 (11) | 142 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x, y+1, z−1; (iv) x, y, z−1. |
R.m.s. deviation (Å) of the plane of atoms C1/C3–C9/O3 and deviation (Å)
of the atom from the plane topMolecule | r.m.s. | O1 | O2 | C2 | C10 |
A | 0.0209 | -0.175 (8) | 0.126 (8) | 0.655 (10) | 0.444 (12) |
B | 0.0288 | 0.141 (10) | -0.254 (9) | -0.714 (11) | -0.541 (13) |
C | 0.0236 | -0.172 (9) | 0.213 (9) | 0.707 (10) | 0.504 (13) |
D | 0.0186 | 0.195 (9) | -0.172 (9) | -0.688 (10) | -0.478 (13) |
E | 0.0322 | -0.133 (9) | 0.275 (9) | 0.774 (10) | 0.100 (12) |
F | 0.0230 | 0.153 (9) | -0.243 (8) | -0.710 (10) | -0.516 (13) |
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