The molecular structure of the title compound [systematic name: 5,7,4′,5′′,7′′,4′′′-hexamethoxy-3′,8′′-biflavone trihydrate], C
36H
30O
10·3H
2O, contains two flavone groups linked by a C—C single bond. In the crystal structure, centrosymmetric clusters are formed
via intermolecular O—H
O hydrogen bonds involving the hexamethoxy-3′,8′′-biflavone molecules and solvent water molecules.
Supporting information
CCDC reference: 610832
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.012 Å
- R factor = 0.087
- wR factor = 0.269
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low .... 29 Perc.
Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12
PLAT417_ALERT_2_B Short Inter D-H..H-D H111 .. H112 .. 1.94 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H112 .. H112 .. 1.50 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H122 .. H131 .. 1.82 Ang.
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.269
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT084_ALERT_2_C High R2 Value .................................. 0.27
PLAT213_ALERT_2_C Atom C32 has ADP max/min Ratio ............. 3.50 prolat
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.14 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio
PLAT417_ALERT_2_C Short Inter D-H..H-D H111 .. H131 .. 2.14 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D H111 .. H132 .. 2.10 Ang.
1 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
5,7,4',5'',7'',4'''-hexamethoxy-3',8''-biflavone trihydrate
top
Crystal data top
C36H30O10·3H2O | Z = 2 |
Mr = 676.65 | F(000) = 712 |
Triclinic, P1 | Dx = 1.305 Mg m−3 |
Hall symbol: -P 1 | Melting point: 512 K |
a = 10.275 (1) Å | Cu Kα radiation, λ = 1.54180 Å |
b = 11.398 (1) Å | Cell parameters from 25 reflections |
c = 15.068 (1) Å | θ = 4.0–20.6° |
α = 91.95 (1)° | µ = 0.84 mm−1 |
β = 91.13 (1)° | T = 299 K |
γ = 102.40 (1)° | Prism, yellow |
V = 1721.9 (3) Å3 | 0.20 × 0.10 × 0.03 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.066 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 2.9° |
Graphite monochromator | h = −12→12 |
ω/2θ scans | k = −13→2 |
7441 measured reflections | l = −17→17 |
6128 independent reflections | 3 standard reflections every 120 min |
1753 reflections with I > 2σ(I) | intensity decay: 3.0% |
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)] = 0.087 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.269 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0995P)2] where P = (Fo2 + 2Fc2)/3 |
6128 reflections | (Δ/σ)max = 0.008 |
448 parameters | Δρmax = 0.51 e Å−3 |
9 restraints | Δρmin = −0.31 e Å−3 |
Special details top
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 | |
O1 | 0.6677 (5) | 0.5116 (4) | 0.2072 (3) | 0.0469 (14) | |
O2 | 1.0498 (5) | 0.9368 (5) | 0.3493 (4) | 0.0548 (15) | |
O3 | 0.1662 (6) | 0.6609 (5) | 0.3580 (4) | 0.0756 (19) | |
O4 | 0.6614 (6) | 0.1556 (5) | 0.1860 (4) | 0.0724 (19) | |
O5 | 1.0952 (5) | 0.6358 (5) | 0.1044 (4) | 0.0545 (15) | |
O6 | 0.9071 (6) | 0.2124 (5) | 0.1212 (4) | 0.0678 (18) | |
O7 | 0.7052 (5) | 0.6420 (5) | 0.0396 (4) | 0.0581 (16) | |
O8 | 0.9918 (6) | 1.2739 (5) | 0.3971 (4) | 0.0692 (19) | |
O9 | 1.3805 (6) | 0.9682 (7) | 0.5750 (4) | 0.087 (2) | |
O10 | 1.2032 (6) | 1.3082 (5) | 0.5120 (4) | 0.0727 (19) | |
C1 | 0.2585 (9) | 0.6002 (8) | 0.3279 (5) | 0.052 (2) | |
C2 | 0.2413 (9) | 0.4768 (8) | 0.3306 (6) | 0.069 (3) | |
H2 | 0.1647 | 0.4307 | 0.3539 | 0.083* | |
C3 | 0.3398 (9) | 0.4231 (8) | 0.2982 (6) | 0.066 (3) | |
H3 | 0.3280 | 0.3400 | 0.2998 | 0.080* | |
C4 | 0.4567 (8) | 0.4890 (8) | 0.2631 (5) | 0.046 (2) | |
C5 | 0.4662 (8) | 0.6123 (7) | 0.2591 (5) | 0.051 (2) | |
H5 | 0.5408 | 0.6587 | 0.2337 | 0.061* | |
C6 | 0.3718 (8) | 0.6675 (8) | 0.2903 (5) | 0.056 (2) | |
H6 | 0.3824 | 0.7503 | 0.2868 | 0.068* | |
C7 | 0.5607 (7) | 0.4300 (7) | 0.2317 (5) | 0.042 (2) | |
C8 | 0.5567 (8) | 0.3103 (7) | 0.2238 (5) | 0.053 (2) | |
H8 | 0.4796 | 0.2565 | 0.2391 | 0.064* | |
C9 | 0.6679 (8) | 0.2644 (7) | 0.1924 (5) | 0.049 (2) | |
C10 | 0.7848 (8) | 0.3548 (7) | 0.1675 (5) | 0.041 (2) | |
C11 | 0.7802 (8) | 0.4771 (7) | 0.1769 (5) | 0.043 (2) | |
C12 | 0.8804 (8) | 0.5712 (7) | 0.1534 (5) | 0.0381 (19) | |
C13 | 0.9977 (8) | 0.5416 (7) | 0.1261 (5) | 0.045 (2) | |
C14 | 1.0094 (8) | 0.4215 (7) | 0.1147 (5) | 0.045 (2) | |
H14 | 1.0876 | 0.4035 | 0.0936 | 0.054* | |
C15 | 0.9047 (9) | 0.3316 (7) | 0.1348 (5) | 0.051 (2) | |
C16 | 0.8552 (7) | 0.6956 (6) | 0.1577 (5) | 0.0351 (18) | |
C17 | 0.7633 (7) | 0.7284 (7) | 0.1019 (5) | 0.044 (2) | |
C18 | 0.7308 (8) | 0.8394 (7) | 0.1099 (6) | 0.055 (2) | |
H18 | 0.6658 | 0.8590 | 0.0729 | 0.066* | |
C19 | 0.7973 (8) | 0.9213 (7) | 0.1747 (6) | 0.058 (2) | |
H19 | 0.7775 | 0.9971 | 0.1798 | 0.069* | |
C20 | 0.8916 (7) | 0.8935 (7) | 0.2314 (5) | 0.043 (2) | |
C21 | 0.9225 (7) | 0.7798 (6) | 0.2221 (5) | 0.043 (2) | |
H21 | 0.9879 | 0.7602 | 0.2588 | 0.051* | |
C22 | 0.9602 (7) | 0.9808 (7) | 0.3002 (5) | 0.043 (2) | |
C23 | 0.9418 (8) | 1.0933 (7) | 0.3160 (5) | 0.050 (2) | |
H23 | 0.8779 | 1.1198 | 0.2822 | 0.060* | |
C24 | 1.0172 (8) | 1.1733 (8) | 0.3827 (5) | 0.053 (2) | |
C25 | 1.1174 (8) | 1.1265 (7) | 0.4301 (5) | 0.043 (2) | |
C26 | 1.1280 (8) | 1.0081 (8) | 0.4143 (6) | 0.051 (2) | |
C27 | 1.2118 (8) | 0.9499 (8) | 0.4574 (6) | 0.059 (2) | |
H27 | 1.2147 | 0.8709 | 0.4419 | 0.071* | |
C28 | 1.2924 (9) | 1.0138 (10) | 0.5253 (6) | 0.067 (3) | |
C29 | 1.2932 (9) | 1.1342 (10) | 0.5433 (6) | 0.070 (3) | |
H29 | 1.3515 | 1.1777 | 0.5866 | 0.083* | |
C30 | 1.2086 (8) | 1.1886 (8) | 0.4976 (6) | 0.057 (2) | |
C31 | 0.0525 (9) | 0.5953 (9) | 0.4014 (7) | 0.091 (3) | |
H31A | 0.0011 | 0.6500 | 0.4242 | 0.137* | |
H31B | 0.0813 | 0.5529 | 0.4494 | 0.137* | |
H31C | −0.0013 | 0.5388 | 0.3596 | 0.137* | |
C32 | 1.0252 (10) | 0.1833 (8) | 0.0864 (7) | 0.100 (4) | |
H32A | 1.0147 | 0.0975 | 0.0821 | 0.150* | |
H32B | 1.1000 | 0.2173 | 0.1252 | 0.150* | |
H32C | 1.0401 | 0.2154 | 0.0285 | 0.150* | |
C33 | 1.2192 (7) | 0.6130 (8) | 0.0733 (6) | 0.063 (3) | |
H33A | 1.2794 | 0.6880 | 0.0631 | 0.094* | |
H33B | 1.2033 | 0.5653 | 0.0189 | 0.094* | |
H33C | 1.2577 | 0.5706 | 0.1172 | 0.094* | |
C34 | 0.6044 (9) | 0.6672 (9) | −0.0183 (6) | 0.090 (4) | |
H34A | 0.5727 | 0.5992 | −0.0584 | 0.135* | |
H34B | 0.6407 | 0.7363 | −0.0517 | 0.135* | |
H34C | 0.5318 | 0.6828 | 0.0160 | 0.135* | |
C35 | 1.3777 (11) | 0.8434 (11) | 0.5624 (8) | 0.113 (4) | |
H35A | 1.4381 | 0.8204 | 0.6045 | 0.170* | |
H35B | 1.4039 | 0.8275 | 0.5032 | 0.170* | |
H35C | 1.2890 | 0.7980 | 0.5712 | 0.170* | |
C36 | 1.2995 (9) | 1.3771 (9) | 0.5741 (7) | 0.104 (4) | |
H36A | 1.2819 | 1.4560 | 0.5828 | 0.156* | |
H36B | 1.3873 | 1.3835 | 0.5515 | 0.156* | |
H36C | 1.2937 | 1.3380 | 0.6298 | 0.156* | |
O11 | 0.3809 (10) | 0.9122 (8) | 0.0005 (6) | 0.188 (4) | |
H111 | 0.3724 | 0.9558 | 0.0467 | 0.226* | |
H112 | 0.4529 | 0.9477 | −0.0231 | 0.226* | |
O12 | 0.4431 (15) | 0.9931 (13) | 0.2560 (9) | 0.335 (9) | |
H121 | 0.4644 | 0.9482 | 0.2949 | 0.402* | |
H122 | 0.4219 | 0.9493 | 0.2083 | 0.402* | |
O13 | 0.2263 (16) | 0.970 (2) | 0.1411 (14) | 0.499 (18) | |
H131 | 0.2538 | 0.9088 | 0.1603 | 0.599* | |
H132 | 0.1768 | 0.9413 | 0.0906 | 0.599* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.052 (3) | 0.039 (3) | 0.053 (4) | 0.017 (3) | 0.005 (3) | −0.004 (3) |
O2 | 0.065 (4) | 0.038 (3) | 0.063 (4) | 0.015 (3) | −0.012 (3) | −0.006 (3) |
O3 | 0.065 (4) | 0.065 (4) | 0.105 (5) | 0.030 (4) | 0.033 (4) | 0.000 (4) |
O4 | 0.073 (4) | 0.030 (4) | 0.114 (6) | 0.010 (3) | 0.014 (4) | 0.006 (3) |
O5 | 0.056 (4) | 0.040 (4) | 0.068 (4) | 0.012 (3) | 0.016 (3) | −0.001 (3) |
O6 | 0.086 (4) | 0.037 (4) | 0.092 (5) | 0.035 (3) | 0.028 (4) | 0.007 (3) |
O7 | 0.075 (4) | 0.043 (4) | 0.059 (4) | 0.023 (3) | −0.018 (3) | −0.012 (3) |
O8 | 0.085 (4) | 0.037 (4) | 0.085 (5) | 0.016 (3) | −0.002 (4) | −0.020 (3) |
O9 | 0.070 (4) | 0.107 (6) | 0.085 (5) | 0.028 (4) | −0.020 (4) | 0.005 (5) |
O10 | 0.068 (4) | 0.063 (4) | 0.080 (5) | 0.004 (4) | −0.013 (4) | −0.020 (4) |
C1 | 0.058 (6) | 0.048 (6) | 0.054 (6) | 0.020 (5) | 0.008 (5) | 0.004 (4) |
C2 | 0.060 (6) | 0.047 (6) | 0.101 (8) | 0.006 (5) | 0.037 (5) | 0.017 (5) |
C3 | 0.071 (6) | 0.044 (6) | 0.090 (8) | 0.023 (5) | 0.020 (5) | 0.007 (5) |
C4 | 0.040 (5) | 0.050 (6) | 0.051 (6) | 0.016 (4) | −0.003 (4) | −0.005 (4) |
C5 | 0.048 (5) | 0.037 (5) | 0.067 (6) | 0.008 (4) | 0.014 (4) | −0.009 (4) |
C6 | 0.065 (6) | 0.042 (5) | 0.065 (6) | 0.017 (5) | 0.017 (5) | 0.000 (5) |
C7 | 0.037 (5) | 0.034 (5) | 0.054 (6) | 0.004 (4) | 0.003 (4) | 0.012 (4) |
C8 | 0.053 (5) | 0.030 (5) | 0.076 (7) | 0.008 (4) | 0.008 (5) | 0.004 (4) |
C9 | 0.058 (6) | 0.035 (5) | 0.061 (6) | 0.026 (4) | −0.009 (4) | −0.010 (4) |
C10 | 0.047 (5) | 0.023 (4) | 0.057 (6) | 0.016 (4) | 0.002 (4) | −0.002 (4) |
C11 | 0.050 (5) | 0.045 (5) | 0.037 (5) | 0.020 (4) | −0.002 (4) | 0.005 (4) |
C12 | 0.042 (5) | 0.029 (4) | 0.045 (5) | 0.015 (4) | 0.001 (4) | −0.006 (4) |
C13 | 0.048 (5) | 0.039 (5) | 0.050 (6) | 0.013 (4) | 0.001 (4) | 0.005 (4) |
C14 | 0.045 (5) | 0.037 (5) | 0.054 (6) | 0.013 (4) | 0.006 (4) | −0.001 (4) |
C15 | 0.069 (6) | 0.038 (5) | 0.052 (6) | 0.028 (5) | −0.002 (5) | 0.004 (4) |
C16 | 0.037 (4) | 0.025 (4) | 0.044 (5) | 0.006 (4) | 0.001 (4) | −0.003 (4) |
C17 | 0.044 (5) | 0.045 (5) | 0.045 (5) | 0.014 (4) | −0.009 (4) | −0.005 (4) |
C18 | 0.059 (5) | 0.038 (5) | 0.073 (7) | 0.022 (4) | −0.007 (5) | −0.004 (5) |
C19 | 0.067 (6) | 0.032 (5) | 0.078 (7) | 0.022 (4) | 0.000 (5) | −0.005 (5) |
C20 | 0.049 (5) | 0.032 (5) | 0.051 (6) | 0.014 (4) | −0.001 (4) | −0.004 (4) |
C21 | 0.042 (5) | 0.032 (5) | 0.057 (6) | 0.012 (4) | 0.004 (4) | 0.005 (4) |
C22 | 0.047 (5) | 0.047 (5) | 0.040 (5) | 0.019 (4) | 0.002 (4) | 0.006 (4) |
C23 | 0.054 (5) | 0.034 (5) | 0.063 (6) | 0.010 (4) | −0.007 (4) | −0.005 (4) |
C24 | 0.056 (5) | 0.050 (6) | 0.049 (6) | 0.004 (5) | 0.011 (4) | −0.013 (5) |
C25 | 0.047 (5) | 0.048 (5) | 0.036 (5) | 0.012 (4) | 0.001 (4) | −0.006 (4) |
C26 | 0.045 (5) | 0.058 (6) | 0.052 (6) | 0.016 (5) | 0.000 (4) | −0.011 (5) |
C27 | 0.064 (6) | 0.064 (6) | 0.055 (6) | 0.026 (5) | 0.008 (5) | −0.001 (5) |
C28 | 0.056 (6) | 0.083 (8) | 0.060 (7) | 0.013 (6) | −0.011 (5) | 0.009 (6) |
C29 | 0.059 (6) | 0.083 (8) | 0.060 (7) | 0.005 (6) | −0.014 (5) | −0.010 (6) |
C30 | 0.052 (6) | 0.059 (6) | 0.057 (6) | 0.005 (5) | 0.013 (5) | −0.008 (5) |
C31 | 0.077 (7) | 0.098 (9) | 0.108 (9) | 0.034 (7) | 0.047 (6) | 0.019 (7) |
C32 | 0.120 (9) | 0.049 (6) | 0.151 (11) | 0.054 (6) | 0.079 (8) | 0.017 (6) |
C33 | 0.039 (5) | 0.069 (7) | 0.081 (7) | 0.012 (5) | 0.018 (5) | 0.005 (5) |
C34 | 0.092 (7) | 0.087 (8) | 0.095 (8) | 0.037 (6) | −0.041 (6) | −0.034 (7) |
C35 | 0.114 (10) | 0.126 (12) | 0.115 (11) | 0.055 (9) | −0.012 (8) | 0.036 (9) |
C36 | 0.088 (7) | 0.076 (8) | 0.137 (10) | 0.008 (6) | −0.049 (7) | −0.058 (7) |
O11 | 0.249 (11) | 0.136 (9) | 0.169 (9) | 0.019 (8) | 0.021 (8) | 0.005 (7) |
O12 | 0.40 (2) | 0.264 (16) | 0.254 (16) | −0.128 (16) | 0.017 (15) | 0.040 (13) |
O13 | 0.289 (18) | 0.74 (4) | 0.58 (3) | 0.28 (2) | 0.24 (2) | 0.43 (3) |
Geometric parameters (Å, º) top
O1—C7 | 1.346 (8) | C18—C19 | 1.389 (10) |
O1—C11 | 1.380 (8) | C18—H18 | 0.9300 |
O2—C22 | 1.357 (8) | C19—C20 | 1.373 (10) |
O2—C26 | 1.378 (9) | C19—H19 | 0.9300 |
O3—C1 | 1.364 (9) | C20—C21 | 1.402 (9) |
O3—C31 | 1.428 (9) | C20—C22 | 1.470 (10) |
O4—C9 | 1.228 (8) | C21—H21 | 0.9300 |
O5—C13 | 1.356 (8) | C22—C23 | 1.350 (10) |
O5—C33 | 1.438 (8) | C23—C24 | 1.430 (10) |
O6—C15 | 1.373 (8) | C23—H23 | 0.9300 |
O6—C32 | 1.430 (9) | C24—C25 | 1.445 (11) |
O7—C17 | 1.367 (8) | C25—C26 | 1.390 (10) |
O7—C34 | 1.423 (9) | C25—C30 | 1.429 (10) |
O8—C24 | 1.243 (9) | C26—C27 | 1.361 (11) |
O9—C28 | 1.361 (10) | C27—C28 | 1.386 (11) |
O9—C35 | 1.423 (11) | C27—H27 | 0.9300 |
O10—C30 | 1.386 (10) | C28—C29 | 1.388 (12) |
O10—C36 | 1.433 (9) | C29—C30 | 1.361 (11) |
C1—C2 | 1.382 (11) | C29—H29 | 0.9300 |
C1—C6 | 1.391 (10) | C31—H31A | 0.9600 |
C2—C3 | 1.379 (10) | C31—H31B | 0.9600 |
C2—H2 | 0.9300 | C31—H31C | 0.9600 |
C3—C4 | 1.397 (10) | C32—H32A | 0.9600 |
C3—H3 | 0.9300 | C32—H32B | 0.9600 |
C4—C5 | 1.391 (10) | C32—H32C | 0.9600 |
C4—C7 | 1.458 (10) | C33—H33A | 0.9600 |
C5—C6 | 1.349 (10) | C33—H33B | 0.9600 |
C5—H5 | 0.9300 | C33—H33C | 0.9600 |
C6—H6 | 0.9300 | C34—H34A | 0.9600 |
C7—C8 | 1.357 (10) | C34—H34B | 0.9600 |
C8—C9 | 1.437 (10) | C34—H34C | 0.9600 |
C8—H8 | 0.9300 | C35—H35A | 0.9600 |
C9—C10 | 1.469 (10) | C35—H35B | 0.9600 |
C10—C11 | 1.407 (10) | C35—H35C | 0.9600 |
C10—C15 | 1.409 (10) | C36—H36A | 0.9600 |
C11—C12 | 1.379 (10) | C36—H36B | 0.9600 |
C12—C13 | 1.385 (9) | C36—H36C | 0.9600 |
C12—C16 | 1.495 (9) | O11—H111 | 0.8574 |
C13—C14 | 1.405 (10) | O11—H112 | 0.8536 |
C14—C15 | 1.363 (10) | O12—H121 | 0.8475 |
C14—H14 | 0.9300 | O12—H122 | 0.8579 |
C16—C17 | 1.371 (9) | O13—H131 | 0.8641 |
C16—C21 | 1.402 (9) | O13—H132 | 0.9178 |
C17—C18 | 1.379 (10) | | |
| | | |
C7—O1—C11 | 121.2 (6) | C16—C21—H21 | 119.9 |
C22—O2—C26 | 120.5 (6) | C20—C21—H21 | 119.9 |
C1—O3—C31 | 118.4 (7) | C23—C22—O2 | 121.1 (8) |
C13—O5—C33 | 119.0 (6) | C23—C22—C20 | 126.6 (8) |
C15—O6—C32 | 118.1 (7) | O2—C22—C20 | 112.4 (7) |
C17—O7—C34 | 118.4 (6) | C22—C23—C24 | 122.4 (8) |
C28—O9—C35 | 117.1 (8) | C22—C23—H23 | 118.8 |
C30—O10—C36 | 116.6 (7) | C24—C23—H23 | 118.8 |
O3—C1—C2 | 122.9 (8) | O8—C24—C23 | 119.6 (8) |
O3—C1—C6 | 117.2 (8) | O8—C24—C25 | 125.2 (8) |
C2—C1—C6 | 119.9 (8) | C23—C24—C25 | 115.2 (8) |
C3—C2—C1 | 118.8 (8) | C26—C25—C30 | 113.3 (8) |
C3—C2—H2 | 120.6 | C26—C25—C24 | 120.0 (8) |
C1—C2—H2 | 120.6 | C30—C25—C24 | 126.6 (8) |
C2—C3—C4 | 122.4 (8) | C27—C26—O2 | 112.9 (8) |
C2—C3—H3 | 118.8 | C27—C26—C25 | 126.5 (8) |
C4—C3—H3 | 118.8 | O2—C26—C25 | 120.6 (8) |
C5—C4—C3 | 116.1 (7) | C26—C27—C28 | 117.0 (9) |
C5—C4—C7 | 122.8 (8) | C26—C27—H27 | 121.5 |
C3—C4—C7 | 121.1 (8) | C28—C27—H27 | 121.5 |
C6—C5—C4 | 122.9 (8) | O9—C28—C27 | 124.1 (10) |
C6—C5—H5 | 118.6 | O9—C28—C29 | 115.2 (9) |
C4—C5—H5 | 118.6 | C27—C28—C29 | 120.6 (10) |
C5—C6—C1 | 119.8 (8) | C30—C29—C28 | 119.9 (9) |
C5—C6—H6 | 120.1 | C30—C29—H29 | 120.1 |
C1—C6—H6 | 120.1 | C28—C29—H29 | 120.1 |
O1—C7—C8 | 121.4 (7) | C29—C30—O10 | 123.3 (9) |
O1—C7—C4 | 110.7 (7) | C29—C30—C25 | 122.5 (9) |
C8—C7—C4 | 127.9 (8) | O10—C30—C25 | 114.3 (8) |
C7—C8—C9 | 122.0 (8) | O3—C31—H31A | 109.5 |
C7—C8—H8 | 119.0 | O3—C31—H31B | 109.5 |
C9—C8—H8 | 119.0 | H31A—C31—H31B | 109.5 |
O4—C9—C8 | 120.5 (8) | O3—C31—H31C | 109.5 |
O4—C9—C10 | 123.6 (7) | H31A—C31—H31C | 109.5 |
C8—C9—C10 | 115.9 (7) | H31B—C31—H31C | 109.5 |
C11—C10—C15 | 115.2 (8) | O6—C32—H32A | 109.5 |
C11—C10—C9 | 118.5 (7) | O6—C32—H32B | 109.5 |
C15—C10—C9 | 126.2 (7) | H32A—C32—H32B | 109.5 |
C12—C11—O1 | 114.2 (7) | O6—C32—H32C | 109.5 |
C12—C11—C10 | 124.8 (8) | H32A—C32—H32C | 109.5 |
O1—C11—C10 | 120.9 (7) | H32B—C32—H32C | 109.5 |
C11—C12—C13 | 116.4 (7) | O5—C33—H33A | 109.5 |
C11—C12—C16 | 118.6 (7) | O5—C33—H33B | 109.5 |
C13—C12—C16 | 124.9 (8) | H33A—C33—H33B | 109.5 |
O5—C13—C12 | 115.3 (7) | O5—C33—H33C | 109.5 |
O5—C13—C14 | 122.8 (7) | H33A—C33—H33C | 109.5 |
C12—C13—C14 | 121.7 (8) | H33B—C33—H33C | 109.5 |
C15—C14—C13 | 119.2 (8) | O7—C34—H34A | 109.5 |
C15—C14—H14 | 120.4 | O7—C34—H34B | 109.5 |
C13—C14—H14 | 120.4 | H34A—C34—H34B | 109.5 |
C14—C15—O6 | 122.2 (7) | O7—C34—H34C | 109.5 |
C14—C15—C10 | 122.3 (7) | H34A—C34—H34C | 109.5 |
O6—C15—C10 | 115.4 (8) | H34B—C34—H34C | 109.5 |
C17—C16—C21 | 118.8 (7) | O9—C35—H35A | 109.5 |
C17—C16—C12 | 121.3 (7) | O9—C35—H35B | 109.5 |
C21—C16—C12 | 119.8 (7) | H35A—C35—H35B | 109.5 |
O7—C17—C16 | 114.9 (7) | O9—C35—H35C | 109.5 |
O7—C17—C18 | 123.1 (7) | H35A—C35—H35C | 109.5 |
C16—C17—C18 | 122.0 (8) | H35B—C35—H35C | 109.5 |
C17—C18—C19 | 118.4 (8) | O10—C36—H36A | 109.5 |
C17—C18—H18 | 120.8 | O10—C36—H36B | 109.5 |
C19—C18—H18 | 120.8 | H36A—C36—H36B | 109.5 |
C20—C19—C18 | 121.9 (8) | O10—C36—H36C | 109.5 |
C20—C19—H19 | 119.1 | H36A—C36—H36C | 109.5 |
C18—C19—H19 | 119.1 | H36B—C36—H36C | 109.5 |
C19—C20—C21 | 118.6 (8) | H111—O11—H112 | 105.7 |
C19—C20—C22 | 121.2 (7) | H121—O12—H122 | 106.8 |
C21—C20—C22 | 120.2 (7) | H131—O13—H132 | 104.4 |
C16—C21—C20 | 120.2 (7) | | |
| | | |
C31—O3—C1—C2 | 5.7 (12) | C11—C12—C16—C21 | 111.0 (8) |
C31—O3—C1—C6 | −176.6 (8) | C13—C12—C16—C21 | −70.0 (11) |
O3—C1—C2—C3 | 179.7 (8) | C34—O7—C17—C16 | 177.3 (7) |
C6—C1—C2—C3 | 2.0 (14) | C34—O7—C17—C18 | −1.4 (12) |
C1—C2—C3—C4 | 0.4 (15) | C21—C16—C17—O7 | 178.2 (7) |
C2—C3—C4—C5 | −2.7 (13) | C12—C16—C17—O7 | −4.3 (11) |
C2—C3—C4—C7 | 178.2 (9) | C21—C16—C17—C18 | −3.1 (12) |
C3—C4—C5—C6 | 2.8 (13) | C12—C16—C17—C18 | 174.4 (8) |
C7—C4—C5—C6 | −178.1 (8) | O7—C17—C18—C19 | −179.0 (8) |
C4—C5—C6—C1 | −0.6 (13) | C16—C17—C18—C19 | 2.4 (13) |
O3—C1—C6—C5 | −179.7 (8) | C17—C18—C19—C20 | −1.4 (13) |
C2—C1—C6—C5 | −1.9 (13) | C18—C19—C20—C21 | 1.2 (13) |
C11—O1—C7—C8 | −3.1 (11) | C18—C19—C20—C22 | −179.4 (8) |
C11—O1—C7—C4 | 178.6 (6) | C17—C16—C21—C20 | 2.8 (11) |
C5—C4—C7—O1 | 5.6 (11) | C12—C16—C21—C20 | −174.8 (7) |
C3—C4—C7—O1 | −175.3 (7) | C19—C20—C21—C16 | −1.8 (12) |
C5—C4—C7—C8 | −172.5 (9) | C22—C20—C21—C16 | 178.7 (7) |
C3—C4—C7—C8 | 6.5 (13) | C26—O2—C22—C23 | −2.5 (11) |
O1—C7—C8—C9 | 2.7 (13) | C26—O2—C22—C20 | 177.0 (7) |
C4—C7—C8—C9 | −179.4 (8) | C19—C20—C22—C23 | −0.4 (13) |
C7—C8—C9—O4 | 179.9 (9) | C21—C20—C22—C23 | 179.1 (8) |
C7—C8—C9—C10 | −1.4 (12) | C19—C20—C22—O2 | −179.8 (7) |
O4—C9—C10—C11 | 179.3 (8) | C21—C20—C22—O2 | −0.4 (10) |
C8—C9—C10—C11 | 0.6 (11) | O2—C22—C23—C24 | 1.7 (12) |
O4—C9—C10—C15 | −1.1 (13) | C20—C22—C23—C24 | −177.7 (8) |
C8—C9—C10—C15 | −179.7 (8) | C22—C23—C24—O8 | −176.6 (8) |
C7—O1—C11—C12 | 179.3 (7) | C22—C23—C24—C25 | 2.0 (12) |
C7—O1—C11—C10 | 2.4 (10) | O8—C24—C25—C26 | 173.5 (8) |
C15—C10—C11—C12 | 2.6 (12) | C23—C24—C25—C26 | −5.0 (12) |
C9—C10—C11—C12 | −177.7 (7) | O8—C24—C25—C30 | −3.5 (14) |
C15—C10—C11—O1 | 179.2 (7) | C23—C24—C25—C30 | 178.0 (8) |
C9—C10—C11—O1 | −1.1 (11) | C22—O2—C26—C27 | 179.6 (7) |
O1—C11—C12—C13 | 177.4 (6) | C22—O2—C26—C25 | −0.7 (11) |
C10—C11—C12—C13 | −5.9 (12) | C30—C25—C26—C27 | 1.6 (13) |
O1—C11—C12—C16 | −3.5 (10) | C24—C25—C26—C27 | −175.9 (8) |
C10—C11—C12—C16 | 173.2 (7) | C30—C25—C26—O2 | −178.1 (7) |
C33—O5—C13—C12 | −178.5 (7) | C24—C25—C26—O2 | 4.5 (13) |
C33—O5—C13—C14 | −3.8 (11) | O2—C26—C27—C28 | −178.6 (8) |
C11—C12—C13—O5 | −179.3 (7) | C25—C26—C27—C28 | 1.7 (14) |
C16—C12—C13—O5 | 1.7 (11) | C35—O9—C28—C27 | −7.4 (14) |
C11—C12—C13—C14 | 6.0 (11) | C35—O9—C28—C29 | 176.4 (9) |
C16—C12—C13—C14 | −173.1 (8) | C26—C27—C28—O9 | 179.5 (8) |
O5—C13—C14—C15 | −177.4 (7) | C26—C27—C28—C29 | −4.5 (14) |
C12—C13—C14—C15 | −3.0 (12) | O9—C28—C29—C30 | −179.7 (8) |
C13—C14—C15—O6 | 176.8 (7) | C27—C28—C29—C30 | 3.9 (15) |
C13—C14—C15—C10 | −0.5 (12) | C28—C29—C30—O10 | 179.8 (8) |
C32—O6—C15—C14 | 1.3 (12) | C28—C29—C30—C25 | −0.4 (14) |
C32—O6—C15—C10 | 178.7 (8) | C36—O10—C30—C29 | 4.5 (13) |
C11—C10—C15—C14 | 0.7 (11) | C36—O10—C30—C25 | −175.4 (8) |
C9—C10—C15—C14 | −178.9 (8) | C26—C25—C30—C29 | −2.2 (12) |
C11—C10—C15—O6 | −176.7 (7) | C24—C25—C30—C29 | 175.0 (9) |
C9—C10—C15—O6 | 3.6 (12) | C26—C25—C30—O10 | 177.7 (7) |
C11—C12—C16—C17 | −66.5 (11) | C24—C25—C30—O10 | −5.1 (12) |
C13—C12—C16—C17 | 112.5 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H111···O13 | 0.86 | 2.12 | 2.82 (2) | 139 |
O11—H112···O11i | 0.85 | 2.09 | 2.810 (19) | 142 |
O12—H121···O9ii | 0.85 | 2.53 | 3.061 (16) | 122 |
O12—H122···O13 | 0.86 | 2.29 | 2.76 (2) | 114 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+2, −z+1. |