Osajin [systematic name: 5-hydroxy-3-(3-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-4
H,8
H-pyrano[2,3-
h]chromen-4-one, C
25H
24O
5, crystallizes with two independent molecules in the asymmetric unit. The benzopyranone ring system is nearly planar in both molecules and they differ significantly only in the orientation of the benzene rings, which are rotated by 56.27 (7) and 44.16 (7)° with respect to the benzopyranone systems. In the crystal structure, intermolecular O—H
O hydrogen bonds link the molecules into dimers.
Supporting information
CCDC reference: 274385
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.125
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.85 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.71 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.57 su
PLAT432_ALERT_2_C Short Inter X...Y Contact C22 .. C22 .. 3.15 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C22A .. C22A .. 3.18 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
3 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: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).
5-hydroxy-3-(3-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-
4H,8
H-pyrano[2,3-
h]chromen-4-one
top
Crystal data top
C25H24O5 | Z = 4 |
Mr = 404.44 | F(000) = 856 |
Triclinic, P1 | Dx = 1.316 Mg m−3 |
a = 8.8220 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.641 (2) Å | Cell parameters from 2831 reflections |
c = 21.504 (3) Å | θ = 2.0–27.6° |
α = 75.865 (11)° | µ = 0.09 mm−1 |
β = 87.731 (10)° | T = 120 K |
γ = 72.474 (12)° | Prism, yellow |
V = 2040.7 (5) Å3 | 0.50 × 0.50 × 0.40 mm |
Data collection top
Kuma KM-4 + CCD diffractometer | 3734 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Enhance (Oxford Diffraction) monochromator | θmax = 25.0°, θmin = 3.0° |
Detector resolution: 16.3 pixels mm-1 | h = −10→10 |
rotation method, ω–scan | k = −11→13 |
14158 measured reflections | l = −25→25 |
7159 independent reflections | |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.01P] where P = (Fo2 + 2Fc2)/3 |
7159 reflections | (Δ/σ)max < 0.001 |
563 parameters | Δρmax = 0.37 e Å−3 |
4 restraints | Δρmin = −0.23 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 | 0.5820 (2) | 0.78798 (16) | 0.31745 (8) | 0.0236 (5) | |
O2 | 0.1209 (2) | 0.82577 (17) | 0.36785 (9) | 0.0294 (5) | |
O3 | 0.5654 (2) | 0.50623 (16) | 0.19317 (8) | 0.0230 (5) | |
O4 | 0.1068 (2) | 0.67496 (18) | 0.30042 (9) | 0.0306 (5) | |
O5 | 0.1751 (2) | 1.07659 (18) | 0.59410 (9) | 0.0303 (5) | |
C1 | 0.5141 (3) | 0.8513 (2) | 0.36154 (12) | 0.0222 (7) | |
H1 | 0.5777 | 0.8886 | 0.3797 | 0.027* | |
C2 | 0.3660 (3) | 0.8663 (2) | 0.38189 (12) | 0.0195 (6) | |
C3 | 0.2648 (3) | 0.8122 (2) | 0.35430 (12) | 0.0222 (7) | |
C4 | 0.3407 (3) | 0.7356 (2) | 0.31079 (12) | 0.0202 (6) | |
C5 | 0.2607 (3) | 0.6654 (2) | 0.28614 (12) | 0.0220 (7) | |
C6 | 0.3369 (3) | 0.5877 (2) | 0.24726 (12) | 0.0195 (6) | |
C7 | 0.4936 (3) | 0.5845 (2) | 0.23124 (12) | 0.0199 (6) | |
C8 | 0.5789 (3) | 0.6506 (2) | 0.25416 (12) | 0.0210 (7) | |
C9 | 0.4988 (3) | 0.7241 (2) | 0.29441 (12) | 0.0194 (6) | |
C10 | 0.7445 (3) | 0.6317 (2) | 0.23727 (13) | 0.0239 (7) | |
H10 | 0.8120 | 0.6600 | 0.2592 | 0.029* | |
C11 | 0.8001 (3) | 0.5750 (2) | 0.19123 (13) | 0.0258 (7) | |
H11 | 0.9098 | 0.5577 | 0.1821 | 0.031* | |
C12 | 0.6924 (3) | 0.5376 (2) | 0.15327 (12) | 0.0241 (7) | |
C13 | 0.6141 (3) | 0.6421 (2) | 0.09523 (12) | 0.0294 (7) | |
H13A | 0.5416 | 0.6156 | 0.0725 | 0.044* | |
H13B | 0.6963 | 0.6617 | 0.0663 | 0.044* | |
H13C | 0.5543 | 0.7161 | 0.1097 | 0.044* | |
C14 | 0.7776 (3) | 0.4196 (2) | 0.13212 (13) | 0.0302 (7) | |
H14A | 0.8234 | 0.3523 | 0.1699 | 0.045* | |
H14B | 0.8626 | 0.4340 | 0.1034 | 0.045* | |
H14C | 0.7016 | 0.3963 | 0.1094 | 0.045* | |
C15 | 0.2525 (3) | 0.5158 (2) | 0.21955 (12) | 0.0230 (7) | |
H15A | 0.3283 | 0.4344 | 0.2177 | 0.028* | |
H15B | 0.1659 | 0.5002 | 0.2478 | 0.028* | |
C16 | 0.1841 (3) | 0.5854 (3) | 0.15323 (13) | 0.0244 (7) | |
H16 | 0.1154 | 0.6674 | 0.1497 | 0.029* | |
C17 | 0.2065 (3) | 0.5485 (3) | 0.09929 (14) | 0.0276 (7) | |
C18 | 0.3115 (4) | 0.4242 (3) | 0.09342 (16) | 0.0466 (9) | |
H18A | 0.3647 | 0.3771 | 0.1350 | 0.070* | |
H18B | 0.3915 | 0.4355 | 0.0615 | 0.070* | |
H18C | 0.2470 | 0.3786 | 0.0799 | 0.070* | |
C19 | 0.1247 (4) | 0.6312 (3) | 0.03732 (14) | 0.0446 (9) | |
H19A | 0.0588 | 0.7107 | 0.0447 | 0.067* | |
H19B | 0.0573 | 0.5911 | 0.0209 | 0.067* | |
H19C | 0.2046 | 0.6457 | 0.0059 | 0.067* | |
C20 | 0.3106 (3) | 0.9279 (2) | 0.43526 (12) | 0.0202 (6) | |
C21 | 0.1710 (3) | 1.0220 (2) | 0.43289 (13) | 0.0275 (7) | |
H21 | 0.1048 | 1.0514 | 0.3950 | 0.033* | |
C22 | 0.1235 (3) | 1.0756 (2) | 0.48440 (13) | 0.0266 (7) | |
H22 | 0.0283 | 1.1426 | 0.4811 | 0.032* | |
C23 | 0.2173 (3) | 1.0297 (2) | 0.54082 (13) | 0.0224 (6) | |
C24 | 0.3588 (3) | 0.9358 (2) | 0.54430 (13) | 0.0255 (7) | |
H24 | 0.4235 | 0.9056 | 0.5826 | 0.031* | |
C25 | 0.4066 (3) | 0.8855 (2) | 0.49203 (12) | 0.0252 (7) | |
H25 | 0.5050 | 0.8219 | 0.4945 | 0.030* | |
O1A | 1.0782 (2) | 0.29570 (16) | 0.31523 (8) | 0.0236 (5) | |
O2A | 0.6097 (2) | 0.35465 (17) | 0.35758 (8) | 0.0266 (5) | |
O3A | 1.0590 (2) | 0.00868 (16) | 0.19567 (8) | 0.0242 (5) | |
O4A | 0.5938 (2) | 0.19990 (17) | 0.29105 (9) | 0.0271 (5) | |
O5A | 0.6693 (2) | 0.62740 (17) | 0.57690 (9) | 0.0293 (5) | |
C1A | 1.0117 (3) | 0.3612 (2) | 0.35901 (12) | 0.0237 (7) | |
H1A | 1.0772 | 0.3955 | 0.3782 | 0.028* | |
C2A | 0.8596 (3) | 0.3810 (2) | 0.37722 (12) | 0.0221 (7) | |
C3A | 0.7561 (3) | 0.3311 (2) | 0.34743 (12) | 0.0198 (6) | |
C4A | 0.8315 (3) | 0.2511 (2) | 0.30627 (12) | 0.0193 (6) | |
C5A | 0.7508 (3) | 0.1836 (2) | 0.28104 (12) | 0.0198 (6) | |
C6A | 0.8282 (3) | 0.0999 (2) | 0.24535 (12) | 0.0210 (6) | |
C7A | 0.9866 (3) | 0.0907 (2) | 0.23099 (12) | 0.0202 (6) | |
C8A | 1.0717 (3) | 0.1565 (2) | 0.25355 (12) | 0.0190 (6) | |
C9A | 0.9912 (3) | 0.2346 (2) | 0.29172 (12) | 0.0208 (7) | |
C10A | 1.2409 (3) | 0.1314 (2) | 0.24010 (13) | 0.0259 (7) | |
H10A | 1.3085 | 0.1581 | 0.2630 | 0.031* | |
C11A | 1.2985 (3) | 0.0703 (3) | 0.19503 (13) | 0.0288 (7) | |
H11A | 1.4091 | 0.0494 | 0.1873 | 0.035* | |
C12A | 1.1903 (3) | 0.0343 (2) | 0.15643 (12) | 0.0234 (7) | |
C13A | 1.1181 (3) | 0.1389 (2) | 0.09727 (13) | 0.0304 (7) | |
H13D | 1.0421 | 0.1151 | 0.0748 | 0.046* | |
H13E | 1.2028 | 0.1532 | 0.0684 | 0.046* | |
H13F | 1.0631 | 0.2151 | 0.1107 | 0.046* | |
C14A | 1.2745 (3) | −0.0853 (2) | 0.13688 (14) | 0.0307 (7) | |
H14D | 1.3169 | −0.1519 | 0.1753 | 0.046* | |
H14E | 1.3620 | −0.0733 | 0.1091 | 0.046* | |
H14F | 1.1989 | −0.1080 | 0.1136 | 0.046* | |
C15A | 0.7421 (3) | 0.0256 (2) | 0.21950 (12) | 0.0249 (7) | |
H15C | 0.8165 | −0.0576 | 0.2200 | 0.030* | |
H15D | 0.6535 | 0.0141 | 0.2476 | 0.030* | |
C16A | 0.6774 (3) | 0.0898 (2) | 0.15209 (13) | 0.0236 (7) | |
H16A | 0.6072 | 0.1717 | 0.1466 | 0.028* | |
C17A | 0.7042 (3) | 0.0485 (3) | 0.09952 (14) | 0.0289 (7) | |
C18A | 0.8140 (4) | −0.0777 (3) | 0.09660 (16) | 0.0470 (9) | |
H18D | 0.8661 | −0.1210 | 0.1389 | 0.071* | |
H18E | 0.8949 | −0.0675 | 0.0649 | 0.071* | |
H18F | 0.7524 | −0.1264 | 0.0841 | 0.071* | |
C19A | 0.6231 (4) | 0.1275 (3) | 0.03614 (14) | 0.0471 (9) | |
H19D | 0.5563 | 0.2081 | 0.0419 | 0.071* | |
H19E | 0.5567 | 0.0854 | 0.0207 | 0.071* | |
H19F | 0.7036 | 0.1403 | 0.0047 | 0.071* | |
C20A | 0.8051 (3) | 0.4490 (2) | 0.42828 (12) | 0.0225 (7) | |
C21A | 0.7229 (3) | 0.4010 (3) | 0.47936 (12) | 0.0278 (7) | |
H21A | 0.6978 | 0.3267 | 0.4803 | 0.033* | |
C22A | 0.6764 (3) | 0.4598 (2) | 0.52926 (12) | 0.0272 (7) | |
H22A | 0.6197 | 0.4256 | 0.5637 | 0.033* | |
C23A | 0.7119 (3) | 0.5659 (2) | 0.52884 (12) | 0.0224 (6) | |
C24A | 0.7950 (3) | 0.6161 (2) | 0.47841 (13) | 0.0278 (7) | |
H24A | 0.8199 | 0.6902 | 0.4779 | 0.033* | |
C25A | 0.8411 (3) | 0.5571 (2) | 0.42870 (13) | 0.0265 (7) | |
H25A | 0.8982 | 0.5912 | 0.3945 | 0.032* | |
H4O | 0.079 (4) | 0.729 (2) | 0.3284 (12) | 0.063 (7)* | |
H4P | 0.577 (4) | 0.258 (2) | 0.3167 (12) | 0.063 (7)* | |
H5O | 0.0685 (19) | 1.124 (3) | 0.596 (2) | 0.104 (11)* | |
H5P | 0.601 (4) | 0.584 (3) | 0.5994 (17) | 0.104 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0215 (11) | 0.0316 (11) | 0.0229 (10) | −0.0126 (9) | 0.0011 (9) | −0.0108 (9) |
O2 | 0.0203 (11) | 0.0399 (12) | 0.0328 (11) | −0.0097 (9) | 0.0061 (9) | −0.0176 (10) |
O3 | 0.0236 (11) | 0.0215 (10) | 0.0240 (10) | −0.0058 (9) | 0.0032 (9) | −0.0076 (9) |
O4 | 0.0226 (11) | 0.0442 (13) | 0.0336 (12) | −0.0147 (10) | 0.0081 (9) | −0.0204 (10) |
O5 | 0.0313 (13) | 0.0395 (13) | 0.0255 (11) | −0.0112 (10) | 0.0054 (10) | −0.0180 (10) |
C1 | 0.0281 (17) | 0.0236 (16) | 0.0180 (14) | −0.0086 (13) | 0.0001 (13) | −0.0096 (13) |
C2 | 0.0237 (16) | 0.0215 (15) | 0.0154 (14) | −0.0096 (13) | −0.0019 (12) | −0.0042 (12) |
C3 | 0.0228 (16) | 0.0235 (16) | 0.0162 (14) | −0.0053 (13) | −0.0006 (12) | 0.0008 (12) |
C4 | 0.0257 (16) | 0.0197 (15) | 0.0138 (13) | −0.0059 (13) | −0.0008 (12) | −0.0027 (12) |
C5 | 0.0217 (16) | 0.0281 (16) | 0.0175 (14) | −0.0117 (13) | −0.0008 (12) | −0.0025 (13) |
C6 | 0.0226 (16) | 0.0202 (15) | 0.0160 (14) | −0.0078 (13) | −0.0016 (12) | −0.0025 (12) |
C7 | 0.0235 (16) | 0.0178 (15) | 0.0141 (14) | −0.0032 (13) | 0.0002 (12) | 0.0004 (12) |
C8 | 0.0222 (16) | 0.0242 (16) | 0.0158 (14) | −0.0074 (13) | −0.0005 (12) | −0.0026 (13) |
C9 | 0.0185 (15) | 0.0242 (15) | 0.0162 (14) | −0.0098 (13) | −0.0029 (12) | −0.0017 (12) |
C10 | 0.0181 (16) | 0.0308 (17) | 0.0241 (15) | −0.0091 (13) | −0.0013 (13) | −0.0065 (14) |
C11 | 0.0170 (15) | 0.0326 (17) | 0.0268 (16) | −0.0057 (13) | 0.0016 (13) | −0.0076 (14) |
C12 | 0.0254 (16) | 0.0241 (16) | 0.0192 (14) | −0.0041 (13) | 0.0055 (13) | −0.0039 (13) |
C13 | 0.0347 (18) | 0.0265 (16) | 0.0230 (15) | −0.0051 (14) | 0.0040 (14) | −0.0041 (14) |
C14 | 0.0281 (17) | 0.0298 (17) | 0.0273 (16) | −0.0015 (14) | 0.0028 (14) | −0.0063 (14) |
C15 | 0.0206 (15) | 0.0243 (15) | 0.0257 (15) | −0.0078 (13) | 0.0055 (13) | −0.0087 (13) |
C16 | 0.0216 (16) | 0.0243 (16) | 0.0294 (16) | −0.0084 (13) | 0.0015 (13) | −0.0087 (14) |
C17 | 0.0312 (18) | 0.0287 (17) | 0.0276 (16) | −0.0116 (14) | 0.0013 (14) | −0.0124 (14) |
C18 | 0.056 (2) | 0.042 (2) | 0.044 (2) | −0.0093 (18) | 0.0054 (18) | −0.0239 (17) |
C19 | 0.055 (2) | 0.050 (2) | 0.0306 (18) | −0.0148 (18) | −0.0050 (17) | −0.0135 (17) |
C20 | 0.0233 (16) | 0.0184 (15) | 0.0196 (14) | −0.0083 (13) | −0.0022 (12) | −0.0029 (12) |
C21 | 0.0337 (17) | 0.0278 (16) | 0.0207 (15) | −0.0094 (14) | −0.0052 (13) | −0.0041 (13) |
C22 | 0.0293 (16) | 0.0206 (15) | 0.0274 (16) | −0.0046 (13) | 0.0014 (13) | −0.0049 (13) |
C23 | 0.0204 (15) | 0.0277 (16) | 0.0211 (15) | −0.0080 (13) | 0.0033 (12) | −0.0093 (13) |
C24 | 0.0309 (16) | 0.0264 (16) | 0.0207 (14) | −0.0129 (13) | −0.0034 (13) | −0.0023 (13) |
C25 | 0.0258 (16) | 0.0236 (15) | 0.0267 (15) | −0.0082 (13) | 0.0005 (13) | −0.0063 (13) |
O1A | 0.0236 (11) | 0.0278 (11) | 0.0229 (10) | −0.0109 (9) | 0.0024 (9) | −0.0090 (9) |
O2A | 0.0224 (11) | 0.0341 (11) | 0.0241 (10) | −0.0083 (9) | 0.0007 (9) | −0.0089 (9) |
O3A | 0.0247 (11) | 0.0247 (11) | 0.0236 (10) | −0.0075 (9) | 0.0022 (9) | −0.0069 (9) |
O4A | 0.0206 (11) | 0.0366 (12) | 0.0270 (11) | −0.0106 (10) | 0.0025 (9) | −0.0106 (10) |
O5A | 0.0283 (12) | 0.0372 (12) | 0.0262 (11) | −0.0101 (10) | −0.0010 (9) | −0.0139 (10) |
C1A | 0.0309 (18) | 0.0255 (16) | 0.0164 (14) | −0.0115 (14) | −0.0023 (13) | −0.0040 (13) |
C2A | 0.0243 (16) | 0.0197 (15) | 0.0192 (14) | −0.0057 (13) | −0.0024 (13) | 0.0004 (12) |
C3A | 0.0210 (16) | 0.0211 (15) | 0.0158 (14) | −0.0078 (13) | −0.0023 (12) | 0.0007 (12) |
C4A | 0.0207 (16) | 0.0223 (15) | 0.0153 (14) | −0.0089 (13) | −0.0012 (12) | −0.0019 (12) |
C5A | 0.0155 (15) | 0.0253 (15) | 0.0166 (14) | −0.0068 (12) | 0.0016 (12) | −0.0009 (12) |
C6A | 0.0252 (16) | 0.0211 (15) | 0.0160 (14) | −0.0092 (13) | −0.0021 (12) | −0.0001 (12) |
C7A | 0.0249 (16) | 0.0181 (15) | 0.0155 (14) | −0.0038 (13) | −0.0020 (13) | −0.0031 (12) |
C8A | 0.0164 (15) | 0.0215 (15) | 0.0183 (14) | −0.0057 (12) | −0.0001 (12) | −0.0030 (13) |
C9A | 0.0287 (17) | 0.0202 (15) | 0.0137 (14) | −0.0095 (13) | −0.0045 (13) | −0.0013 (12) |
C10A | 0.0242 (17) | 0.0270 (16) | 0.0263 (16) | −0.0079 (14) | −0.0025 (14) | −0.0056 (14) |
C11A | 0.0202 (16) | 0.0313 (17) | 0.0336 (17) | −0.0067 (14) | 0.0026 (14) | −0.0074 (15) |
C12A | 0.0214 (16) | 0.0258 (16) | 0.0199 (15) | −0.0036 (13) | 0.0024 (13) | −0.0047 (13) |
C13A | 0.0343 (18) | 0.0237 (16) | 0.0281 (16) | −0.0043 (14) | 0.0033 (14) | −0.0023 (14) |
C14A | 0.0304 (18) | 0.0266 (16) | 0.0311 (17) | −0.0019 (14) | 0.0021 (14) | −0.0082 (14) |
C15A | 0.0286 (16) | 0.0254 (16) | 0.0231 (15) | −0.0106 (13) | 0.0000 (13) | −0.0072 (13) |
C16A | 0.0217 (16) | 0.0208 (15) | 0.0286 (16) | −0.0065 (13) | −0.0022 (13) | −0.0059 (13) |
C17A | 0.0321 (18) | 0.0306 (17) | 0.0283 (17) | −0.0118 (15) | 0.0045 (14) | −0.0129 (15) |
C18A | 0.058 (2) | 0.040 (2) | 0.047 (2) | −0.0102 (18) | 0.0026 (18) | −0.0224 (17) |
C19A | 0.061 (2) | 0.054 (2) | 0.0301 (18) | −0.022 (2) | −0.0078 (17) | −0.0097 (17) |
C20A | 0.0284 (17) | 0.0247 (15) | 0.0179 (14) | −0.0122 (13) | 0.0009 (13) | −0.0063 (13) |
C21A | 0.0381 (18) | 0.0256 (16) | 0.0208 (15) | −0.0127 (14) | −0.0025 (13) | −0.0028 (13) |
C22A | 0.0328 (17) | 0.0314 (17) | 0.0170 (14) | −0.0128 (14) | 0.0029 (13) | −0.0014 (13) |
C23A | 0.0224 (15) | 0.0255 (16) | 0.0190 (14) | −0.0046 (13) | −0.0025 (12) | −0.0079 (13) |
C24A | 0.0301 (17) | 0.0223 (15) | 0.0312 (16) | −0.0078 (13) | −0.0012 (13) | −0.0068 (13) |
C25A | 0.0313 (16) | 0.0272 (16) | 0.0213 (14) | −0.0115 (13) | 0.0028 (13) | −0.0033 (13) |
Geometric parameters (Å, º) top
O1—C1 | 1.353 (3) | O1A—C1A | 1.359 (3) |
O1—C9 | 1.369 (3) | O1A—C9A | 1.373 (3) |
O2—C3 | 1.262 (3) | O2A—C3A | 1.259 (3) |
O3—C7 | 1.370 (3) | O3A—C7A | 1.359 (3) |
O3—C12 | 1.463 (3) | O3A—C12A | 1.466 (3) |
O4—C5 | 1.358 (3) | O4A—C5A | 1.357 (3) |
O4—H4O | 0.946 (10) | O4A—H4P | 0.953 (10) |
O5—C23 | 1.378 (3) | O5A—C23A | 1.375 (3) |
O5—H5O | 0.94 (3) | O5A—H5P | 0.95 (4) |
C1—C2 | 1.336 (3) | C1A—C2A | 1.350 (4) |
C1—H1 | 0.9500 | C1A—H1A | 0.9500 |
C2—C3 | 1.452 (4) | C2A—C3A | 1.459 (4) |
C2—C20 | 1.489 (4) | C2A—C20A | 1.489 (4) |
C3—C4 | 1.455 (4) | C3A—C4A | 1.441 (4) |
C4—C9 | 1.400 (4) | C4A—C9A | 1.397 (4) |
C4—C5 | 1.426 (4) | C4A—C5A | 1.412 (3) |
C5—C6 | 1.389 (4) | C5A—C6A | 1.388 (4) |
C6—C7 | 1.403 (4) | C6A—C7A | 1.398 (4) |
C6—C15 | 1.505 (3) | C6A—C15A | 1.516 (4) |
C7—C8 | 1.401 (4) | C7A—C8A | 1.394 (3) |
C8—C9 | 1.390 (4) | C8A—C9A | 1.391 (4) |
C8—C10 | 1.455 (4) | C8A—C10A | 1.463 (4) |
C10—C11 | 1.320 (4) | C10A—C11A | 1.336 (4) |
C10—H10 | 0.9500 | C10A—H10A | 0.9500 |
C11—C12 | 1.498 (4) | C11A—C12A | 1.500 (4) |
C11—H11 | 0.9500 | C11A—H11A | 0.9500 |
C12—C14 | 1.522 (4) | C12A—C14A | 1.519 (4) |
C12—C13 | 1.528 (3) | C12A—C13A | 1.532 (3) |
C13—H13A | 0.9800 | C13A—H13D | 0.9800 |
C13—H13B | 0.9800 | C13A—H13E | 0.9800 |
C13—H13C | 0.9800 | C13A—H13F | 0.9800 |
C14—H14A | 0.9800 | C14A—H14D | 0.9800 |
C14—H14B | 0.9800 | C14A—H14E | 0.9800 |
C14—H14C | 0.9800 | C14A—H14F | 0.9800 |
C15—C16 | 1.505 (3) | C15A—C16A | 1.505 (3) |
C15—H15A | 0.9900 | C15A—H15C | 0.9900 |
C15—H15B | 0.9900 | C15A—H15D | 0.9900 |
C16—C17 | 1.321 (4) | C16A—C17A | 1.319 (4) |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
C17—C18 | 1.497 (4) | C17A—C18A | 1.511 (4) |
C17—C19 | 1.502 (4) | C17A—C19A | 1.511 (4) |
C18—H18A | 0.9800 | C18A—H18D | 0.9800 |
C18—H18B | 0.9800 | C18A—H18E | 0.9800 |
C18—H18C | 0.9800 | C18A—H18F | 0.9800 |
C19—H19A | 0.9800 | C19A—H19D | 0.9800 |
C19—H19B | 0.9800 | C19A—H19E | 0.9800 |
C19—H19C | 0.9800 | C19A—H19F | 0.9800 |
C20—C21 | 1.373 (4) | C20A—C21A | 1.388 (3) |
C20—C25 | 1.410 (4) | C20A—C25A | 1.389 (4) |
C21—C22 | 1.391 (4) | C21A—C22A | 1.394 (4) |
C21—H21 | 0.9500 | C21A—H21A | 0.9500 |
C22—C23 | 1.392 (4) | C22A—C23A | 1.361 (4) |
C22—H22 | 0.9500 | C22A—H22A | 0.9500 |
C23—C24 | 1.380 (4) | C23A—C24A | 1.393 (3) |
C24—C25 | 1.385 (4) | C24A—C25A | 1.392 (4) |
C24—H24 | 0.9500 | C24A—H24A | 0.9500 |
C25—H25 | 0.9500 | C25A—H25A | 0.9500 |
| | | |
C1—O1—C9 | 118.5 (2) | C1A—O1A—C9A | 118.6 (2) |
C7—O3—C12 | 116.7 (2) | C7A—O3A—C12A | 117.0 (2) |
C5—O4—H4O | 106 (2) | C5A—O4A—H4P | 98 (2) |
C23—O5—H5O | 118 (3) | C23A—O5A—H5P | 100 (3) |
C2—C1—O1 | 126.1 (3) | C2A—C1A—O1A | 124.9 (3) |
C2—C1—H1 | 117.0 | C2A—C1A—H1A | 117.6 |
O1—C1—H1 | 117.0 | O1A—C1A—H1A | 117.6 |
C1—C2—C3 | 118.3 (3) | C1A—C2A—C3A | 118.5 (3) |
C1—C2—C20 | 120.7 (3) | C1A—C2A—C20A | 119.1 (3) |
C3—C2—C20 | 120.8 (3) | C3A—C2A—C20A | 122.4 (3) |
O2—C3—C2 | 123.5 (3) | O2A—C3A—C4A | 121.5 (3) |
O2—C3—C4 | 120.6 (3) | O2A—C3A—C2A | 122.3 (3) |
C2—C3—C4 | 115.9 (3) | C4A—C3A—C2A | 116.1 (3) |
C9—C4—C5 | 117.9 (3) | C9A—C4A—C5A | 117.5 (3) |
C9—C4—C3 | 120.3 (3) | C9A—C4A—C3A | 120.3 (3) |
C5—C4—C3 | 121.7 (3) | C5A—C4A—C3A | 122.2 (3) |
O4—C5—C6 | 119.0 (3) | O4A—C5A—C6A | 118.2 (3) |
O4—C5—C4 | 119.7 (3) | O4A—C5A—C4A | 120.2 (2) |
C6—C5—C4 | 121.3 (3) | C6A—C5A—C4A | 121.6 (3) |
C5—C6—C7 | 117.4 (3) | C5A—C6A—C7A | 117.8 (3) |
C5—C6—C15 | 121.8 (2) | C5A—C6A—C15A | 121.5 (3) |
C7—C6—C15 | 120.7 (2) | C7A—C6A—C15A | 120.6 (3) |
O3—C7—C8 | 120.1 (2) | O3A—C7A—C8A | 120.3 (2) |
O3—C7—C6 | 115.8 (3) | O3A—C7A—C6A | 116.5 (3) |
C8—C7—C6 | 124.0 (3) | C8A—C7A—C6A | 123.1 (3) |
C9—C8—C7 | 116.2 (3) | C9A—C8A—C7A | 116.8 (3) |
C9—C8—C10 | 125.5 (3) | C9A—C8A—C10A | 124.7 (3) |
C7—C8—C10 | 118.2 (3) | C7A—C8A—C10A | 118.3 (3) |
O1—C9—C8 | 116.5 (2) | O1A—C9A—C8A | 116.1 (2) |
O1—C9—C4 | 120.4 (3) | O1A—C9A—C4A | 120.9 (3) |
C8—C9—C4 | 123.1 (3) | C8A—C9A—C4A | 123.0 (3) |
C11—C10—C8 | 119.5 (3) | C11A—C10A—C8A | 118.7 (3) |
C11—C10—H10 | 120.2 | C11A—C10A—H10A | 120.7 |
C8—C10—H10 | 120.2 | C8A—C10A—H10A | 120.7 |
C10—C11—C12 | 120.8 (3) | C10A—C11A—C12A | 120.7 (3) |
C10—C11—H11 | 119.6 | C10A—C11A—H11A | 119.7 |
C12—C11—H11 | 119.6 | C12A—C11A—H11A | 119.7 |
O3—C12—C11 | 110.3 (2) | O3A—C12A—C11A | 109.7 (2) |
O3—C12—C14 | 104.3 (2) | O3A—C12A—C14A | 105.4 (2) |
C11—C12—C14 | 112.3 (2) | C11A—C12A—C14A | 111.8 (2) |
O3—C12—C13 | 107.7 (2) | O3A—C12A—C13A | 107.8 (2) |
C11—C12—C13 | 111.7 (2) | C11A—C12A—C13A | 111.4 (2) |
C14—C12—C13 | 110.2 (2) | C14A—C12A—C13A | 110.4 (2) |
C12—C13—H13A | 109.5 | C12A—C13A—H13D | 109.5 |
C12—C13—H13B | 109.5 | C12A—C13A—H13E | 109.5 |
H13A—C13—H13B | 109.5 | H13D—C13A—H13E | 109.5 |
C12—C13—H13C | 109.5 | C12A—C13A—H13F | 109.5 |
H13A—C13—H13C | 109.5 | H13D—C13A—H13F | 109.5 |
H13B—C13—H13C | 109.5 | H13E—C13A—H13F | 109.5 |
C12—C14—H14A | 109.5 | C12A—C14A—H14D | 109.5 |
C12—C14—H14B | 109.5 | C12A—C14A—H14E | 109.5 |
H14A—C14—H14B | 109.5 | H14D—C14A—H14E | 109.5 |
C12—C14—H14C | 109.5 | C12A—C14A—H14F | 109.5 |
H14A—C14—H14C | 109.5 | H14D—C14A—H14F | 109.5 |
H14B—C14—H14C | 109.5 | H14E—C14A—H14F | 109.5 |
C16—C15—C6 | 111.2 (2) | C16A—C15A—C6A | 111.4 (2) |
C16—C15—H15A | 109.4 | C16A—C15A—H15C | 109.4 |
C6—C15—H15A | 109.4 | C6A—C15A—H15C | 109.4 |
C16—C15—H15B | 109.4 | C16A—C15A—H15D | 109.4 |
C6—C15—H15B | 109.4 | C6A—C15A—H15D | 109.4 |
H15A—C15—H15B | 108.0 | H15C—C15A—H15D | 108.0 |
C17—C16—C15 | 128.9 (3) | C17A—C16A—C15A | 129.3 (3) |
C17—C16—H16 | 115.5 | C17A—C16A—H16A | 115.4 |
C15—C16—H16 | 115.5 | C15A—C16A—H16A | 115.4 |
C16—C17—C18 | 124.7 (3) | C16A—C17A—C18A | 124.5 (3) |
C16—C17—C19 | 121.3 (3) | C16A—C17A—C19A | 120.9 (3) |
C18—C17—C19 | 114.0 (3) | C18A—C17A—C19A | 114.6 (3) |
C17—C18—H18A | 109.5 | C17A—C18A—H18D | 109.5 |
C17—C18—H18B | 109.5 | C17A—C18A—H18E | 109.5 |
H18A—C18—H18B | 109.5 | H18D—C18A—H18E | 109.5 |
C17—C18—H18C | 109.5 | C17A—C18A—H18F | 109.5 |
H18A—C18—H18C | 109.5 | H18D—C18A—H18F | 109.5 |
H18B—C18—H18C | 109.5 | H18E—C18A—H18F | 109.5 |
C17—C19—H19A | 109.5 | C17A—C19A—H19D | 109.5 |
C17—C19—H19B | 109.5 | C17A—C19A—H19E | 109.5 |
H19A—C19—H19B | 109.5 | H19D—C19A—H19E | 109.5 |
C17—C19—H19C | 109.5 | C17A—C19A—H19F | 109.5 |
H19A—C19—H19C | 109.5 | H19D—C19A—H19F | 109.5 |
H19B—C19—H19C | 109.5 | H19E—C19A—H19F | 109.5 |
C21—C20—C25 | 118.1 (3) | C21A—C20A—C25A | 117.9 (3) |
C21—C20—C2 | 124.0 (2) | C21A—C20A—C2A | 119.9 (2) |
C25—C20—C2 | 117.8 (2) | C25A—C20A—C2A | 122.1 (2) |
C20—C21—C22 | 121.9 (3) | C20A—C21A—C22A | 121.2 (3) |
C20—C21—H21 | 119.1 | C20A—C21A—H21A | 119.4 |
C22—C21—H21 | 119.1 | C22A—C21A—H21A | 119.4 |
C21—C22—C23 | 119.2 (3) | C23A—C22A—C21A | 120.2 (3) |
C21—C22—H22 | 120.4 | C23A—C22A—H22A | 119.9 |
C23—C22—H22 | 120.4 | C21A—C22A—H22A | 119.9 |
O5—C23—C24 | 117.8 (2) | C22A—C23A—O5A | 122.6 (2) |
O5—C23—C22 | 122.1 (3) | C22A—C23A—C24A | 120.0 (3) |
C24—C23—C22 | 120.1 (3) | O5A—C23A—C24A | 117.4 (2) |
C23—C24—C25 | 120.1 (3) | C25A—C24A—C23A | 119.6 (3) |
C23—C24—H24 | 120.0 | C25A—C24A—H24A | 120.2 |
C25—C24—H24 | 120.0 | C23A—C24A—H24A | 120.2 |
C24—C25—C20 | 120.6 (3) | C20A—C25A—C24A | 121.1 (3) |
C24—C25—H25 | 119.7 | C20A—C25A—H25A | 119.4 |
C20—C25—H25 | 119.7 | C24A—C25A—H25A | 119.4 |
| | | |
C13—C12—C11—C10 | 87.8 (3) | C13A—C12A—C11A—C10A | 87.1 (3) |
C14—C12—C11—C10 | −147.8 (3) | C14A—C12A—C11A—C10A | −148.7 (3) |
O2—C3—C4—C5 | −5.2 (4) | O2A—C3A—C4A—C5A | −7.4 (4) |
H4O—O4—C5—C4 | −3 (2) | H4P—O4A—C5A—C4A | −1.7 (19) |
C5—C6—C15—C16 | 94.0 (3) | C5A—C6A—C15A—C16A | 93.5 (3) |
C6—C15—C16—C17 | 125.1 (3) | C6A—C15A—C16A—C17A | 122.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O2 | 0.95 (1) | 1.70 (2) | 2.567 (3) | 151 (3) |
O4A—H4P···O2A | 0.95 (1) | 1.68 (3) | 2.596 (3) | 162 (3) |
O5—H5O···O2i | 0.94 (3) | 1.81 (2) | 2.698 (3) | 157 (4) |
O5A—H5P···O2Aii | 0.95 (4) | 2.05 (3) | 2.765 (3) | 131 (3) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1. |