Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026114/na6268sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026114/na6268Isup2.hkl |
CCDC reference: 227900
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.121
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ? PLAT481_ALERT_4_A Long D...A H-Bond Reported [C]O6 .. O5 = 2.66 Ang.
Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 93 PerFit PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... c PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup . P21/c
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.61 PLAT481_ALERT_4_C Long D...A H-Bond Reported [F]C23 .. O3 = 3.46 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported [G]C23 .. O4 = 3.48 Ang. PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... [A]O2 [A]O2 H2A PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... [B]O2 [B]O2 H2A PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... [C]O6 [C]O6 H6A PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... [D]O6 [D]O6 H6A PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... [E]C19 [E]C19 H19 PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... [F]C23 [F]C23 H23A PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... [G]C23 [G]C23 H23B PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... [A]O2 [A]O2 O1 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... [B]O2 [B]O2 O8 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... [C]O6 [C]O6 O5 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... [D]O6 [D]O6 O7 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... [E]C19 [E]C19 O6 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... [F]C23 [F]C23 O3 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... [G]C23 [G]C23 O4 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... [A]O2 [A]O2 H2A O1 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... [B]O2 [B]O2 H2A O8 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... [C]O6 [C]O6 H6A O5 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... [D]O6 [D]O6 H6A O7 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... [E]C19 [E]C19 H19 O6 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... [F]C23 [F]C23 H23A O3 PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... [G]C23 [G]C23 H23B O4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C4 H8 O2
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 29.97 From the CIF: _reflns_number_total 3479 Count of symmetry unique reflns 3483 Completeness (_total/calc) 99.89% 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
2 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 26 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 23 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: TEXSAN-TEXRAY (Molecular Structure Corporation, 1985); cell refinement: TEXSAN-TEXRAY; data reduction: TEXSAN-TEXRAY; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.
C20H22O6·C4H8O2 | F(000) = 476 |
Mr = 446.48 | Dx = 1.346 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 9.8318 (16) Å | θ = 23.4–24.9° |
b = 6.066 (3) Å | µ = 0.10 mm−1 |
c = 18.493 (2) Å | T = 153 K |
β = 92.891 (13)° | Plate, colourless |
V = 1101.5 (6) Å3 | 0.55 × 0.35 × 0.35 mm |
Z = 2 |
Rigaku AFC6 diffractometer | Rint = 0.013 |
Radiation source: normal-focus rotating anode | θmax = 30.0°, θmin = 2.1° |
Graphite monochromator | h = 0→13 |
ω scans | k = 0→8 |
3660 measured reflections | l = −25→25 |
3479 independent reflections | 3 standard reflections every 150 reflections |
2765 reflections with I > 2σI | intensity decay: none |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0679P)2 + 0.1302P] where P = (Fo2 + 2Fc2)/3 |
3479 reflections | (Δ/σ)max < 0.001 |
311 parameters | Δρmax = 0.33 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
Experimental. Data were collected at low temperature using a Rigaku AFC6R diffractometer equiped with a low temperature device. The data were collected using ω-scan. Scans of (1.22 + 0.30tanθ) were made at a speed of 8.0ο/min. The weak reflections (I<10.0σI) were rescanned (maximum 3 rescans) and the counts were accumulated to assure good counting statistics. Stationary bacground counts were recored on each side of the reflection. The ratio of peak counting time to backgroud counting time was 2:1. The crystal–to–detector distance was 400 mm. |
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 | 0.86723 (18) | 0.7651 (4) | 0.39457 (10) | 0.0237 (4) | |
C2 | 0.78063 (19) | 0.6263 (4) | 0.43133 (10) | 0.0248 (4) | |
H2 | 0.7484 | 0.4974 | 0.4093 | 0.042 (8)* | |
C3 | 0.74239 (18) | 0.6788 (4) | 0.50015 (10) | 0.0228 (4) | |
C4 | 0.79078 (19) | 0.8737 (4) | 0.53375 (10) | 0.0245 (4) | |
C5 | 0.8747 (2) | 1.0127 (4) | 0.49705 (11) | 0.0273 (4) | |
H5 | 0.9060 | 1.1427 | 0.5188 | 0.043 (8)* | |
C6 | 0.91258 (19) | 0.9590 (4) | 0.42766 (11) | 0.0262 (4) | |
H6 | 0.9688 | 1.0539 | 0.4033 | 0.042 (8)* | |
C7 | 0.5873 (2) | 0.3774 (4) | 0.50649 (13) | 0.0316 (5) | |
H7A | 0.5392 | 0.4286 | 0.4632 | 0.036 (7)* | |
H7B | 0.5237 | 0.3164 | 0.5387 | 0.052 (9)* | |
H7C | 0.6516 | 0.2661 | 0.4942 | 0.044 (8)* | |
C8 | 0.91926 (19) | 0.6906 (4) | 0.32359 (10) | 0.0255 (4) | |
H8 | 0.9848 | 0.5711 | 0.3331 | 0.038 (7)* | |
C9 | 0.9850 (2) | 0.8631 (4) | 0.27647 (10) | 0.0263 (4) | |
H9 | 0.9351 | 1.0029 | 0.2765 | 0.029 (7)* | |
C10 | 1.1386 (2) | 0.8986 (5) | 0.29093 (11) | 0.0335 (5) | |
H10A | 1.1580 | 1.0537 | 0.2991 | 0.040* | |
H10B | 1.1708 | 0.8164 | 0.3334 | 0.040* | |
C11 | 1.15336 (18) | 0.6312 (4) | 0.11523 (10) | 0.0254 (4) | |
C12 | 1.23149 (19) | 0.7870 (4) | 0.08078 (10) | 0.0261 (4) | |
H12 | 1.2661 | 0.9084 | 0.1063 | 0.046 (8)* | |
C13 | 1.25762 (19) | 0.7606 (4) | 0.00794 (10) | 0.0250 (4) | |
C14 | 1.20537 (19) | 0.5794 (4) | −0.03067 (10) | 0.0276 (4) | |
C15 | 1.1261 (2) | 0.4272 (4) | 0.00362 (11) | 0.0311 (5) | |
H15 | 1.0891 | 0.3081 | −0.0222 | 0.039 (8)* | |
C16 | 1.1013 (2) | 0.4517 (4) | 0.07677 (11) | 0.0293 (4) | |
H16 | 1.0495 | 0.3471 | 0.0998 | 0.034 (7)* | |
C17 | 1.4086 (2) | 1.0689 (4) | 0.00630 (13) | 0.0339 (5) | |
H17A | 1.3457 | 1.1710 | 0.0260 | 0.045 (8)* | |
H17B | 1.4651 | 1.1451 | −0.0264 | 0.051 (9)* | |
H17C | 1.4646 | 1.0053 | 0.0449 | 0.048 (8)* | |
C18 | 1.11777 (19) | 0.6620 (4) | 0.19303 (10) | 0.0262 (4) | |
H18 | 1.1279 | 0.5212 | 0.2187 | 0.039 (7)* | |
C19 | 0.97340 (19) | 0.7513 (4) | 0.20150 (10) | 0.0283 (4) | |
H19 | 0.9491 | 0.8590 | 0.1635 | 0.033 (7)* | |
C20 | 0.8610 (2) | 0.5794 (6) | 0.20753 (11) | 0.0430 (7) | |
H20A | 0.7896 | 0.6026 | 0.1702 | 0.052* | |
H20B | 0.8975 | 0.4321 | 0.2022 | 0.052* | |
C21 | 1.4511 (3) | 0.5275 (5) | −0.23373 (13) | 0.0390 (6) | |
H21A | 1.3798 | 0.4182 | −0.2299 | 0.047* | |
H21B | 1.5376 | 0.4575 | −0.2206 | 0.047* | |
C22 | 1.4521 (3) | 0.6092 (6) | −0.30944 (13) | 0.0560 (9) | |
H22A | 1.4701 | 0.4875 | −0.3416 | 0.067* | |
H22B | 1.3633 | 0.6694 | −0.3237 | 0.067* | |
C23 | 1.5316 (2) | 0.9530 (5) | −0.26788 (13) | 0.0366 (5) | |
H23A | 1.4453 | 1.0235 | −0.2811 | 0.044* | |
H23B | 1.6033 | 1.0617 | −0.2715 | 0.044* | |
C24 | 1.5301 (3) | 0.8708 (6) | −0.19247 (13) | 0.0517 (8) | |
H24A | 1.6188 | 0.8103 | −0.1782 | 0.062* | |
H24B | 1.5124 | 0.9927 | −0.1603 | 0.062* | |
O1 | 0.65778 (15) | 0.5576 (3) | 0.54108 (7) | 0.0295 (3) | |
O2 | 0.75570 (17) | 0.9280 (3) | 0.60194 (8) | 0.0353 (4) | |
H2A | 0.6918 | 0.8507 | 0.6134 | 0.051 (9)* | |
O3 | 0.80826 (15) | 0.6066 (4) | 0.27825 (8) | 0.0402 (5) | |
O4 | 1.20418 (14) | 0.8221 (4) | 0.22813 (7) | 0.0348 (4) | |
O5 | 1.33514 (16) | 0.8991 (3) | −0.03163 (8) | 0.0326 (4) | |
O6 | 1.23224 (18) | 0.5481 (4) | −0.10141 (8) | 0.0416 (5) | |
H6A | 1.2894 | 0.6379 | −0.1133 | 0.060 (10)* | |
O7 | 1.42862 (19) | 0.7052 (4) | −0.18529 (9) | 0.0434 (5) | |
O8 | 1.5538 (2) | 0.7757 (4) | −0.31618 (9) | 0.0467 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0198 (7) | 0.0274 (10) | 0.0239 (8) | −0.0003 (8) | 0.0016 (6) | −0.0013 (8) |
C2 | 0.0229 (8) | 0.0262 (10) | 0.0253 (8) | −0.0019 (8) | 0.0010 (7) | −0.0011 (8) |
C3 | 0.0199 (8) | 0.0233 (9) | 0.0253 (8) | −0.0033 (8) | 0.0019 (6) | 0.0011 (8) |
C4 | 0.0225 (8) | 0.0279 (10) | 0.0230 (8) | −0.0008 (8) | 0.0005 (7) | −0.0014 (8) |
C5 | 0.0260 (9) | 0.0268 (10) | 0.0291 (9) | −0.0053 (9) | 0.0022 (7) | −0.0030 (9) |
C6 | 0.0218 (8) | 0.0301 (11) | 0.0269 (9) | −0.0045 (8) | 0.0034 (7) | 0.0024 (8) |
C7 | 0.0295 (10) | 0.0225 (10) | 0.0435 (12) | −0.0056 (9) | 0.0079 (9) | −0.0025 (9) |
C8 | 0.0216 (8) | 0.0303 (10) | 0.0247 (8) | −0.0028 (8) | 0.0025 (6) | −0.0043 (8) |
C9 | 0.0258 (9) | 0.0314 (11) | 0.0217 (8) | −0.0006 (8) | 0.0024 (7) | 0.0001 (8) |
C10 | 0.0300 (10) | 0.0448 (14) | 0.0260 (9) | −0.0095 (10) | 0.0048 (7) | −0.0041 (10) |
C11 | 0.0194 (8) | 0.0326 (11) | 0.0244 (8) | 0.0010 (8) | 0.0022 (6) | 0.0006 (8) |
C12 | 0.0231 (8) | 0.0283 (10) | 0.0270 (8) | −0.0015 (8) | 0.0017 (7) | −0.0029 (9) |
C13 | 0.0205 (8) | 0.0285 (10) | 0.0262 (8) | −0.0014 (8) | 0.0024 (6) | 0.0012 (8) |
C14 | 0.0232 (8) | 0.0359 (12) | 0.0241 (8) | −0.0034 (9) | 0.0035 (7) | −0.0021 (9) |
C15 | 0.0275 (9) | 0.0345 (12) | 0.0315 (10) | −0.0094 (10) | 0.0029 (8) | −0.0066 (10) |
C16 | 0.0256 (9) | 0.0322 (11) | 0.0305 (10) | −0.0063 (9) | 0.0058 (7) | 0.0001 (9) |
C17 | 0.0349 (10) | 0.0250 (11) | 0.0424 (11) | −0.0069 (9) | 0.0085 (9) | −0.0043 (10) |
C18 | 0.0225 (8) | 0.0315 (11) | 0.0247 (8) | 0.0001 (8) | 0.0015 (7) | 0.0002 (8) |
C19 | 0.0216 (8) | 0.0416 (13) | 0.0215 (8) | 0.0014 (9) | −0.0006 (6) | −0.0002 (9) |
C20 | 0.0276 (10) | 0.072 (2) | 0.0301 (10) | −0.0145 (13) | 0.0072 (8) | −0.0175 (13) |
C21 | 0.0431 (12) | 0.0302 (12) | 0.0450 (13) | −0.0026 (11) | 0.0132 (10) | −0.0003 (11) |
C22 | 0.086 (2) | 0.0508 (18) | 0.0323 (12) | −0.0345 (18) | 0.0166 (13) | −0.0117 (13) |
C23 | 0.0334 (11) | 0.0323 (12) | 0.0451 (12) | −0.0046 (10) | 0.0103 (9) | −0.0004 (11) |
C24 | 0.0679 (18) | 0.0539 (19) | 0.0340 (12) | −0.0288 (16) | 0.0099 (12) | −0.0092 (13) |
O1 | 0.0336 (7) | 0.0288 (8) | 0.0265 (7) | −0.0088 (7) | 0.0062 (5) | 0.0006 (7) |
O2 | 0.0397 (8) | 0.0402 (10) | 0.0267 (7) | −0.0131 (8) | 0.0092 (6) | −0.0074 (7) |
O3 | 0.0266 (7) | 0.0652 (13) | 0.0294 (7) | −0.0172 (9) | 0.0071 (6) | −0.0143 (9) |
O4 | 0.0235 (6) | 0.0541 (11) | 0.0270 (7) | −0.0086 (8) | 0.0037 (5) | −0.0078 (8) |
O5 | 0.0337 (7) | 0.0341 (9) | 0.0304 (7) | −0.0121 (8) | 0.0053 (6) | −0.0010 (7) |
O6 | 0.0446 (9) | 0.0542 (12) | 0.0272 (7) | −0.0235 (10) | 0.0113 (7) | −0.0108 (8) |
O7 | 0.0540 (10) | 0.0442 (11) | 0.0339 (8) | −0.0168 (9) | 0.0202 (7) | −0.0077 (9) |
O8 | 0.0623 (11) | 0.0427 (11) | 0.0375 (8) | −0.0181 (11) | 0.0263 (8) | −0.0075 (9) |
C1—C6 | 1.390 (3) | C14—C15 | 1.383 (3) |
C1—C2 | 1.398 (3) | C15—C16 | 1.395 (3) |
C1—C8 | 1.502 (3) | C15—H15 | 0.9300 |
C2—C3 | 1.382 (3) | C16—H16 | 0.9300 |
C2—H2 | 0.9300 | C17—O5 | 1.423 (3) |
C3—O1 | 1.367 (2) | C17—H17A | 0.9600 |
C3—C4 | 1.407 (3) | C17—H17B | 0.9600 |
C4—O2 | 1.364 (2) | C17—H17C | 0.9600 |
C4—C5 | 1.382 (3) | C18—O4 | 1.425 (3) |
C5—C6 | 1.393 (3) | C18—C19 | 1.535 (3) |
C5—H5 | 0.9300 | C18—H18 | 0.9800 |
C6—H6 | 0.9300 | C19—C20 | 1.528 (4) |
C7—O1 | 1.428 (3) | C19—H19 | 0.9800 |
C7—H7A | 0.9600 | C20—O3 | 1.441 (2) |
C7—H7B | 0.9600 | C20—H20A | 0.9700 |
C7—H7C | 0.9600 | C20—H20B | 0.9700 |
C8—O3 | 1.436 (2) | C21—O7 | 1.426 (3) |
C8—C9 | 1.526 (3) | C21—C22 | 1.486 (4) |
C8—H8 | 0.9800 | C21—H21A | 0.9700 |
C9—C10 | 1.535 (3) | C21—H21B | 0.9700 |
C9—C19 | 1.542 (3) | C22—O8 | 1.431 (3) |
C9—H9 | 0.9800 | C22—H22A | 0.9700 |
C10—O4 | 1.434 (2) | C22—H22B | 0.9700 |
C10—H10A | 0.9700 | C23—O8 | 1.422 (3) |
C10—H10B | 0.9700 | C23—C24 | 1.482 (4) |
C11—C16 | 1.384 (3) | C23—H23A | 0.9700 |
C11—C12 | 1.392 (3) | C23—H23B | 0.9700 |
C11—C18 | 1.509 (3) | C24—O7 | 1.427 (3) |
C12—C13 | 1.393 (3) | C24—H24A | 0.9700 |
C12—H12 | 0.9300 | C24—H24B | 0.9700 |
C13—O5 | 1.370 (3) | O2—H2A | 0.8200 |
C13—C14 | 1.395 (3) | O6—H6A | 0.8200 |
C14—O6 | 1.361 (2) | ||
C6—C1—C2 | 119.04 (18) | C11—C16—H16 | 119.9 |
C6—C1—C8 | 121.58 (18) | C15—C16—H16 | 119.9 |
C2—C1—C8 | 119.12 (19) | O5—C17—H17A | 109.5 |
C3—C2—C1 | 120.7 (2) | O5—C17—H17B | 109.5 |
C3—C2—H2 | 119.7 | H17A—C17—H17B | 109.5 |
C1—C2—H2 | 119.7 | O5—C17—H17C | 109.5 |
O1—C3—C2 | 126.0 (2) | H17A—C17—H17C | 109.5 |
O1—C3—C4 | 114.12 (17) | H17B—C17—H17C | 109.5 |
C2—C3—C4 | 119.89 (19) | O4—C18—C11 | 110.93 (17) |
O2—C4—C5 | 119.4 (2) | O4—C18—C19 | 104.25 (18) |
O2—C4—C3 | 121.02 (19) | C11—C18—C19 | 113.65 (16) |
C5—C4—C3 | 119.53 (18) | O4—C18—H18 | 109.3 |
C4—C5—C6 | 120.3 (2) | C11—C18—H18 | 109.3 |
C4—C5—H5 | 119.9 | C19—C18—H18 | 109.3 |
C6—C5—H5 | 119.9 | C20—C19—C18 | 116.3 (2) |
C1—C6—C5 | 120.60 (19) | C20—C19—C9 | 104.80 (16) |
C1—C6—H6 | 119.7 | C18—C19—C9 | 102.70 (15) |
C5—C6—H6 | 119.7 | C20—C19—H19 | 110.8 |
O1—C7—H7A | 109.5 | C18—C19—H19 | 110.8 |
O1—C7—H7B | 109.5 | C9—C19—H19 | 110.8 |
H7A—C7—H7B | 109.5 | O3—C20—C19 | 106.4 (2) |
O1—C7—H7C | 109.5 | O3—C20—H20A | 110.4 |
H7A—C7—H7C | 109.5 | C19—C20—H20A | 110.4 |
H7B—C7—H7C | 109.5 | O3—C20—H20B | 110.4 |
O3—C8—C1 | 109.55 (15) | C19—C20—H20B | 110.4 |
O3—C8—C9 | 103.96 (16) | H20A—C20—H20B | 108.6 |
C1—C8—C9 | 117.75 (19) | O7—C21—C22 | 110.4 (2) |
O3—C8—H8 | 108.4 | O7—C21—H21A | 109.6 |
C1—C8—H8 | 108.4 | C22—C21—H21A | 109.6 |
C9—C8—H8 | 108.4 | O7—C21—H21B | 109.6 |
C8—C9—C10 | 115.99 (18) | C22—C21—H21B | 109.6 |
C8—C9—C19 | 101.40 (18) | H21A—C21—H21B | 108.1 |
C10—C9—C19 | 104.24 (16) | O8—C22—C21 | 110.8 (2) |
C8—C9—H9 | 111.5 | O8—C22—H22A | 109.5 |
C10—C9—H9 | 111.5 | C21—C22—H22A | 109.5 |
C19—C9—H9 | 111.5 | O8—C22—H22B | 109.5 |
O4—C10—C9 | 106.99 (16) | C21—C22—H22B | 109.5 |
O4—C10—H10A | 110.3 | H22A—C22—H22B | 108.1 |
C9—C10—H10A | 110.3 | O8—C23—C24 | 110.2 (3) |
O4—C10—H10B | 110.3 | O8—C23—H23A | 109.6 |
C9—C10—H10B | 110.3 | C24—C23—H23A | 109.6 |
H10A—C10—H10B | 108.6 | O8—C23—H23B | 109.6 |
C16—C11—C12 | 119.81 (18) | C24—C23—H23B | 109.6 |
C16—C11—C18 | 119.32 (19) | H23A—C23—H23B | 108.1 |
C12—C11—C18 | 120.8 (2) | O7—C24—C23 | 111.4 (2) |
C11—C12—C13 | 119.8 (2) | O7—C24—H24A | 109.4 |
C11—C12—H12 | 120.1 | C23—C24—H24A | 109.4 |
C13—C12—H12 | 120.1 | O7—C24—H24B | 109.4 |
O5—C13—C12 | 125.5 (2) | C23—C24—H24B | 109.4 |
O5—C13—C14 | 114.22 (17) | H24A—C24—H24B | 108.0 |
C12—C13—C14 | 120.29 (19) | C3—O1—C7 | 117.29 (16) |
O6—C14—C15 | 119.3 (2) | C4—O2—H2A | 109.5 |
O6—C14—C13 | 121.2 (2) | C8—O3—C20 | 105.85 (15) |
C15—C14—C13 | 119.55 (18) | C18—O4—C10 | 107.89 (16) |
C14—C15—C16 | 120.3 (2) | C13—O5—C17 | 117.57 (17) |
C14—C15—H15 | 119.9 | C14—O6—H6A | 109.5 |
C16—C15—H15 | 119.9 | C24—O7—C21 | 110.02 (19) |
C11—C16—C15 | 120.3 (2) | C23—O8—C22 | 110.41 (18) |
C6—C1—C2—C3 | −1.2 (3) | C12—C11—C16—C15 | −0.4 (3) |
C8—C1—C2—C3 | 173.12 (18) | C18—C11—C16—C15 | 176.1 (2) |
C1—C2—C3—O1 | 179.45 (19) | C14—C15—C16—C11 | 1.4 (3) |
C1—C2—C3—C4 | 0.0 (3) | C16—C11—C18—O4 | 166.43 (19) |
O1—C3—C4—O2 | 1.2 (3) | C12—C11—C18—O4 | −17.1 (3) |
C2—C3—C4—O2 | −179.30 (19) | C16—C11—C18—C19 | −76.5 (3) |
O1—C3—C4—C5 | −178.51 (19) | C12—C11—C18—C19 | 100.0 (2) |
C2—C3—C4—C5 | 1.0 (3) | O4—C18—C19—C20 | −148.36 (17) |
O2—C4—C5—C6 | 179.4 (2) | C11—C18—C19—C20 | 90.7 (2) |
C3—C4—C5—C6 | −0.8 (3) | O4—C18—C19—C9 | −34.6 (2) |
C2—C1—C6—C5 | 1.3 (3) | C11—C18—C19—C9 | −155.47 (19) |
C8—C1—C6—C5 | −172.8 (2) | C8—C9—C19—C20 | 20.3 (2) |
C4—C5—C6—C1 | −0.3 (3) | C10—C9—C19—C20 | 141.1 (2) |
C6—C1—C8—O3 | −138.4 (2) | C8—C9—C19—C18 | −101.68 (19) |
C2—C1—C8—O3 | 47.5 (3) | C10—C9—C19—C18 | 19.1 (2) |
C6—C1—C8—C9 | −19.9 (3) | C18—C19—C20—O3 | 116.6 (2) |
C2—C1—C8—C9 | 165.94 (18) | C9—C19—C20—O3 | 4.0 (3) |
O3—C8—C9—C10 | −150.31 (19) | O7—C21—C22—O8 | 57.5 (3) |
C1—C8—C9—C10 | 88.3 (2) | O8—C23—C24—O7 | −57.5 (3) |
O3—C8—C9—C19 | −38.1 (2) | C2—C3—O1—C7 | −9.3 (3) |
C1—C8—C9—C19 | −159.49 (16) | C4—C3—O1—C7 | 170.11 (17) |
C8—C9—C10—O4 | 112.8 (2) | C1—C8—O3—C20 | 169.2 (2) |
C19—C9—C10—O4 | 2.3 (3) | C9—C8—O3—C20 | 42.5 (3) |
C16—C11—C12—C13 | −0.5 (3) | C19—C20—O3—C8 | −28.8 (3) |
C18—C11—C12—C13 | −176.90 (18) | C11—C18—O4—C10 | 160.50 (19) |
C11—C12—C13—O5 | −178.5 (2) | C19—C18—O4—C10 | 37.8 (2) |
C11—C12—C13—C14 | 0.3 (3) | C9—C10—O4—C18 | −25.2 (3) |
O5—C13—C14—O6 | 0.4 (3) | C12—C13—O5—C17 | 8.0 (3) |
C12—C13—C14—O6 | −178.5 (2) | C14—C13—O5—C17 | −170.81 (18) |
O5—C13—C14—C15 | 179.7 (2) | C23—C24—O7—C21 | 57.4 (3) |
C12—C13—C14—C15 | 0.7 (3) | C22—C21—O7—C24 | −57.0 (3) |
O6—C14—C15—C16 | 177.7 (2) | C24—C23—O8—C22 | 56.9 (3) |
C13—C14—C15—C16 | −1.6 (3) | C21—C22—O8—C23 | −57.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
[a]O2—H2A···O1 | 0.82 | 2.24 | 2.671 (3) | 113 |
[b]O2—H2A···O8i | 0.82 | 1.98 | 2.718 (2) | 149 |
[c]O6—H6A···O5 | 0.82 | 2.22 | 2.663 (3) | 114 |
[d]O6—H6A···O7 | 0.82 | 2.00 | 2.710 (2) | 145 |
[e]C19—H19···O6ii | 0.98 | 2.37 | 3.221 (3) | 145 |
[f]C23—H23A···O3ii | 0.97 | 2.55 | 3.465 (3) | 158 |
[g]C23—H23B···O4iii | 0.97 | 2.56 | 3.480 (3) | 158 |
Symmetry codes: (i) x−1, y, z+1; (ii) −x+2, y+1/2, −z; (iii) −x+3, y+1/2, −z. |
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