The crystal structure of cholic acid–pentan-3-one (1/1), C5H10O·C24H40O5, has been determined in order to deduce the molecular conformation of the small volatile ketone. Data were collected at 100 K to a resolution of (sin θ)/λ = 0.91 Å−1. The structure contains a hydrogen-bonded cholic acid host network, forming only van der Waals interactions with the guest pentan-3-one molecules. The ketone molecules are disordered on general positions, with two clearly identifiable conformations. The majority conformer exhibits approximate C2 symmetry and is similar to that recently observed by microwave spectroscopy in the gas phase.
Supporting information
CCDC reference: 833418
Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
cholic acid–pentan-3-one (1/1)
top
Crystal data top
C5H10O·C24H40O5 | F(000) = 544 |
Mr = 494.69 | Dx = 1.195 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4097 reflections |
a = 12.5606 (7) Å | θ = 2.5–29.1° |
b = 8.0425 (5) Å | µ = 0.08 mm−1 |
c = 13.9139 (8) Å | T = 100 K |
β = 102.002 (3)° | Fragment, colourless |
V = 1374.84 (14) Å3 | 0.16 × 0.13 × 0.11 mm |
Z = 2 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 9042 reflections with I > 2σ(I) |
Radiation source: Incoatec microsource | Rint = 0.070 |
Multilayer optics monochromator | θmax = 40.4°, θmin = 1.7° |
ω scans | h = −22→14 |
33615 measured reflections | k = −14→14 |
13745 independent reflections | l = −14→24 |
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)] = 0.081 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.085P)2 + 0.250P] where P = (Fo2 + 2Fc2)/3 |
13745 reflections | (Δ/σ)max = 0.002 |
357 parameters | Δρmax = 0.69 e Å−3 |
26 restraints | Δρmin = −0.44 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 | Occ. (<1) |
O1 | 0.69836 (14) | 0.71124 (18) | 1.27098 (11) | 0.0233 (3) | |
H1 | 0.762 (2) | 0.670 (5) | 1.270 (3) | 0.058 (11)* | |
O2 | 0.66149 (14) | 0.46199 (19) | 1.20162 (12) | 0.0265 (3) | |
O3 | 0.19334 (13) | 0.68117 (17) | 0.77718 (10) | 0.0187 (3) | |
H3 | 0.2435 (18) | 0.749 (3) | 0.7951 (19) | 0.020 (6)* | |
O4 | 0.08920 (12) | 0.14850 (16) | 0.70817 (10) | 0.0183 (3) | |
H4 | 0.086 (2) | 0.052 (2) | 0.682 (2) | 0.028 (7)* | |
O5 | −0.09985 (14) | 0.37263 (17) | 0.39354 (10) | 0.0210 (3) | |
H5 | −0.131 (2) | 0.300 (3) | 0.3570 (19) | 0.028 (7)* | |
C1 | 0.63263 (18) | 0.6008 (2) | 1.21892 (14) | 0.0198 (4) | |
C2 | 0.51952 (19) | 0.6700 (3) | 1.18229 (16) | 0.0269 (4) | |
H2A | 0.5250 | 0.7889 | 1.1655 | 0.032* | |
H2B | 0.4782 | 0.6627 | 1.2355 | 0.032* | |
C3 | 0.45794 (18) | 0.5775 (3) | 1.09263 (15) | 0.0205 (4) | |
H3A | 0.4595 | 0.4572 | 1.1079 | 0.025* | |
H3B | 0.4966 | 0.5935 | 1.0382 | 0.025* | |
C4 | 0.33861 (16) | 0.6315 (2) | 1.05719 (13) | 0.0168 (3) | |
H4A | 0.3000 | 0.6163 | 1.1126 | 0.020* | |
C5 | 0.28543 (17) | 0.5161 (2) | 0.97245 (13) | 0.0161 (3) | |
H5A | 0.3262 | 0.5302 | 0.9184 | 0.019* | |
C6 | 0.16201 (16) | 0.5336 (2) | 0.92592 (13) | 0.0145 (3) | |
C7 | 0.12530 (16) | 0.6728 (2) | 0.84903 (13) | 0.0153 (3) | |
H7 | 0.1294 | 0.7819 | 0.8841 | 0.018* | |
C8 | 0.00800 (16) | 0.6458 (2) | 0.79326 (13) | 0.0162 (3) | |
H8A | −0.0099 | 0.7324 | 0.7418 | 0.019* | |
H8B | −0.0412 | 0.6618 | 0.8396 | 0.019* | |
C9 | −0.01560 (16) | 0.4732 (2) | 0.74399 (13) | 0.0140 (3) | |
H9 | 0.0275 | 0.4659 | 0.6913 | 0.017* | |
C10 | 0.02636 (17) | 0.3340 (2) | 0.81938 (13) | 0.0158 (3) | |
H10 | −0.0188 | 0.3369 | 0.8707 | 0.019* | |
C11 | 0.01322 (17) | 0.1614 (2) | 0.77187 (13) | 0.0166 (3) | |
H11 | 0.0327 | 0.0762 | 0.8250 | 0.020* | |
C12 | −0.10390 (18) | 0.1316 (2) | 0.71865 (14) | 0.0193 (4) | |
H12A | −0.1498 | 0.1199 | 0.7681 | 0.023* | |
H12B | −0.1074 | 0.0252 | 0.6823 | 0.023* | |
C13 | −0.15184 (16) | 0.2700 (2) | 0.64605 (13) | 0.0160 (3) | |
H13 | −0.2320 | 0.2494 | 0.6269 | 0.019* | |
C14 | −0.10709 (17) | 0.2569 (2) | 0.55196 (13) | 0.0168 (3) | |
H14A | −0.0269 | 0.2680 | 0.5692 | 0.020* | |
H14B | −0.1242 | 0.1452 | 0.5230 | 0.020* | |
C15 | −0.15237 (17) | 0.3868 (2) | 0.47568 (13) | 0.0171 (3) | |
H15 | −0.2326 | 0.3704 | 0.4530 | 0.021* | |
C16 | −0.12999 (17) | 0.5590 (2) | 0.52070 (14) | 0.0179 (3) | |
H16A | −0.1620 | 0.6444 | 0.4720 | 0.022* | |
H16B | −0.0505 | 0.5781 | 0.5388 | 0.022* | |
C17 | −0.17912 (17) | 0.5745 (2) | 0.61221 (14) | 0.0183 (3) | |
H17A | −0.2591 | 0.5632 | 0.5921 | 0.022* | |
H17B | −0.1636 | 0.6875 | 0.6399 | 0.022* | |
C18 | −0.13689 (16) | 0.4454 (2) | 0.69420 (13) | 0.0157 (3) | |
C19 | −0.21174 (18) | 0.4604 (3) | 0.76871 (15) | 0.0227 (4) | |
H19A | −0.1842 | 0.3890 | 0.8255 | 0.034* | |
H19B | −0.2856 | 0.4257 | 0.7375 | 0.034* | |
H19C | −0.2130 | 0.5762 | 0.7905 | 0.034* | |
C20 | 0.14312 (16) | 0.3667 (2) | 0.87001 (13) | 0.0149 (3) | |
H20 | 0.1866 | 0.3707 | 0.8175 | 0.018* | |
C21 | 0.19700 (18) | 0.2374 (2) | 0.94500 (14) | 0.0193 (4) | |
H21A | 0.2198 | 0.1385 | 0.9119 | 0.023* | |
H21B | 0.1470 | 0.2017 | 0.9875 | 0.023* | |
C22 | 0.29609 (18) | 0.3295 (2) | 1.00487 (15) | 0.0205 (4) | |
H22A | 0.3643 | 0.2814 | 0.9918 | 0.025* | |
H22B | 0.2973 | 0.3197 | 1.0760 | 0.025* | |
C23 | 0.09651 (17) | 0.5475 (2) | 1.00720 (14) | 0.0182 (4) | |
H23A | 0.1223 | 0.4638 | 1.0579 | 0.027* | |
H23B | 0.0192 | 0.5287 | 0.9791 | 0.027* | |
H23C | 0.1062 | 0.6587 | 1.0365 | 0.027* | |
C24 | 0.33062 (19) | 0.8150 (2) | 1.02697 (15) | 0.0221 (4) | |
H24A | 0.3663 | 0.8317 | 0.9714 | 0.033* | |
H24B | 0.3666 | 0.8837 | 1.0825 | 0.033* | |
H24C | 0.2539 | 0.8471 | 1.0077 | 0.033* | |
O6 | 0.46564 (18) | −0.0848 (3) | 0.38832 (16) | 0.0496 (6) | |
C25 | 0.5509 (2) | −0.0080 (5) | 0.4042 (2) | 0.0446 (7) | |
C26 | 0.5881 (2) | 0.0944 (3) | 0.3280 (3) | 0.0416 (7) | |
H26A | 0.6470 | 0.0337 | 0.3055 | 0.050* | |
H26B | 0.6196 | 0.1992 | 0.3589 | 0.050* | |
C27 | 0.5002 (2) | 0.1373 (4) | 0.2388 (2) | 0.0431 (7) | |
H27A | 0.4647 | 0.0350 | 0.2102 | 0.065* | |
H27B | 0.5331 | 0.1944 | 0.1900 | 0.065* | |
H27C | 0.4461 | 0.2101 | 0.2588 | 0.065* | |
C28A | 0.6190 (5) | 0.0254 (8) | 0.5050 (3) | 0.0383 (15) | 0.544 (12) |
H28A | 0.6083 | 0.1424 | 0.5230 | 0.046* | 0.544 (12) |
H28B | 0.6968 | 0.0110 | 0.5029 | 0.046* | 0.544 (12) |
C29A | 0.5915 (13) | −0.0875 (14) | 0.5832 (8) | 0.047 (2) | 0.544 (12) |
H29A | 0.5161 | −0.0682 | 0.5890 | 0.070* | 0.544 (12) |
H29B | 0.6405 | −0.0639 | 0.6463 | 0.070* | 0.544 (12) |
H29C | 0.6001 | −0.2037 | 0.5650 | 0.070* | 0.544 (12) |
C28B | 0.6306 (7) | −0.0765 (15) | 0.4975 (6) | 0.062 (2) | 0.456 (12) |
H28C | 0.6404 | −0.1979 | 0.4915 | 0.075* | 0.456 (12) |
H28D | 0.7026 | −0.0222 | 0.5051 | 0.075* | 0.456 (12) |
C29B | 0.5804 (18) | −0.038 (2) | 0.5864 (10) | 0.062 (3) | 0.456 (12) |
H29D | 0.5487 | 0.0735 | 0.5796 | 0.093* | 0.456 (12) |
H29E | 0.6370 | −0.0440 | 0.6466 | 0.093* | 0.456 (12) |
H29F | 0.5235 | −0.1200 | 0.5899 | 0.093* | 0.456 (12) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0219 (9) | 0.0233 (6) | 0.0229 (7) | −0.0010 (6) | 0.0007 (6) | −0.0021 (5) |
O2 | 0.0246 (9) | 0.0228 (6) | 0.0288 (8) | 0.0018 (6) | −0.0024 (6) | −0.0033 (6) |
O3 | 0.0204 (8) | 0.0212 (6) | 0.0143 (6) | −0.0028 (5) | 0.0033 (5) | 0.0012 (5) |
O4 | 0.0217 (8) | 0.0167 (5) | 0.0160 (6) | 0.0024 (5) | 0.0029 (5) | −0.0039 (5) |
O5 | 0.0325 (9) | 0.0191 (6) | 0.0113 (5) | −0.0044 (6) | 0.0046 (5) | −0.0006 (5) |
C1 | 0.0210 (10) | 0.0230 (8) | 0.0138 (7) | −0.0014 (7) | −0.0006 (7) | −0.0011 (6) |
C2 | 0.0228 (12) | 0.0302 (10) | 0.0247 (10) | 0.0051 (8) | −0.0019 (8) | −0.0086 (8) |
C3 | 0.0182 (10) | 0.0230 (8) | 0.0183 (8) | 0.0025 (7) | −0.0008 (7) | −0.0030 (6) |
C4 | 0.0161 (9) | 0.0209 (7) | 0.0125 (7) | 0.0010 (6) | 0.0011 (6) | −0.0009 (6) |
C5 | 0.0164 (10) | 0.0184 (7) | 0.0127 (7) | 0.0020 (6) | 0.0012 (6) | −0.0022 (6) |
C6 | 0.0166 (9) | 0.0144 (6) | 0.0118 (7) | 0.0031 (6) | 0.0019 (6) | −0.0014 (5) |
C7 | 0.0194 (10) | 0.0138 (6) | 0.0123 (7) | 0.0019 (6) | 0.0022 (6) | −0.0009 (5) |
C8 | 0.0188 (10) | 0.0159 (6) | 0.0132 (7) | 0.0026 (6) | 0.0016 (6) | −0.0001 (6) |
C9 | 0.0152 (9) | 0.0153 (6) | 0.0117 (7) | 0.0017 (6) | 0.0030 (6) | 0.0015 (5) |
C10 | 0.0206 (10) | 0.0158 (6) | 0.0117 (7) | 0.0029 (6) | 0.0048 (6) | 0.0016 (5) |
C11 | 0.0229 (10) | 0.0146 (6) | 0.0119 (7) | 0.0022 (6) | 0.0027 (6) | 0.0019 (5) |
C12 | 0.0253 (11) | 0.0175 (7) | 0.0155 (8) | −0.0039 (7) | 0.0048 (7) | 0.0022 (6) |
C13 | 0.0144 (9) | 0.0183 (7) | 0.0149 (7) | −0.0040 (6) | 0.0026 (6) | 0.0013 (6) |
C14 | 0.0205 (10) | 0.0158 (6) | 0.0136 (7) | −0.0007 (6) | 0.0025 (7) | 0.0005 (6) |
C15 | 0.0198 (10) | 0.0177 (7) | 0.0124 (7) | −0.0017 (6) | −0.0001 (6) | 0.0012 (6) |
C16 | 0.0200 (10) | 0.0163 (7) | 0.0160 (8) | −0.0001 (6) | 0.0004 (7) | 0.0017 (6) |
C17 | 0.0158 (10) | 0.0197 (7) | 0.0181 (8) | 0.0023 (7) | 0.0007 (7) | 0.0004 (6) |
C18 | 0.0146 (9) | 0.0182 (7) | 0.0141 (7) | −0.0001 (6) | 0.0024 (6) | 0.0015 (6) |
C19 | 0.0187 (11) | 0.0293 (9) | 0.0210 (9) | 0.0009 (8) | 0.0064 (8) | 0.0006 (7) |
C20 | 0.0201 (10) | 0.0131 (6) | 0.0113 (7) | 0.0029 (6) | 0.0025 (6) | −0.0003 (5) |
C21 | 0.0242 (11) | 0.0148 (7) | 0.0161 (8) | 0.0032 (7) | −0.0019 (7) | 0.0010 (6) |
C22 | 0.0212 (11) | 0.0161 (7) | 0.0209 (9) | 0.0034 (7) | −0.0030 (7) | 0.0004 (6) |
C23 | 0.0215 (10) | 0.0206 (7) | 0.0128 (7) | 0.0030 (7) | 0.0039 (7) | −0.0030 (6) |
C24 | 0.0264 (11) | 0.0206 (8) | 0.0176 (8) | −0.0010 (7) | 0.0007 (8) | −0.0007 (6) |
O6 | 0.0309 (12) | 0.0763 (16) | 0.0382 (11) | −0.0096 (11) | −0.0003 (9) | 0.0100 (10) |
C25 | 0.0201 (14) | 0.076 (2) | 0.0350 (13) | −0.0049 (13) | −0.0010 (10) | −0.0122 (13) |
C26 | 0.0292 (15) | 0.0341 (12) | 0.0613 (18) | −0.0059 (10) | 0.0088 (13) | −0.0112 (12) |
C27 | 0.0371 (17) | 0.0327 (12) | 0.0599 (18) | −0.0066 (11) | 0.0110 (14) | 0.0003 (12) |
C28A | 0.035 (3) | 0.041 (3) | 0.032 (2) | −0.010 (2) | −0.0076 (19) | 0.002 (2) |
C29A | 0.044 (4) | 0.052 (5) | 0.038 (3) | 0.010 (4) | −0.003 (3) | 0.016 (3) |
C28B | 0.040 (4) | 0.070 (6) | 0.067 (4) | 0.012 (4) | −0.014 (3) | −0.008 (4) |
C29B | 0.064 (7) | 0.076 (9) | 0.040 (4) | 0.000 (7) | −0.004 (4) | 0.023 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.321 (2) | C15—C16 | 1.522 (2) |
O1—H1 | 0.863 (18) | C15—H15 | 1.00 |
O2—C1 | 1.213 (2) | C16—C17 | 1.531 (3) |
O3—C7 | 1.446 (2) | C16—H16A | 0.99 |
O3—H3 | 0.829 (17) | C16—H16B | 0.99 |
O4—C11 | 1.435 (2) | C17—C18 | 1.552 (3) |
O4—H4 | 0.853 (17) | C17—H17A | 0.99 |
O5—C15 | 1.438 (2) | C17—H17B | 0.99 |
O5—H5 | 0.819 (17) | C18—C19 | 1.542 (3) |
C1—C2 | 1.512 (3) | C19—H19A | 0.98 |
C2—C3 | 1.519 (3) | C19—H19B | 0.98 |
C2—H2A | 0.99 | C19—H19C | 0.98 |
C2—H2B | 0.99 | C20—C21 | 1.528 (2) |
C3—C4 | 1.540 (3) | C20—H20 | 1.00 |
C3—H3A | 0.99 | C21—C22 | 1.536 (3) |
C3—H3B | 0.99 | C21—H21A | 0.99 |
C4—C24 | 1.533 (3) | C21—H21B | 0.99 |
C4—C5 | 1.539 (3) | C22—H22A | 0.99 |
C4—H4A | 1.00 | C22—H22B | 0.99 |
C5—C6 | 1.557 (3) | C23—H23A | 0.98 |
C5—C22 | 1.565 (3) | C23—H23B | 0.98 |
C5—H5A | 1.00 | C23—H23C | 0.98 |
C6—C23 | 1.535 (3) | C24—H24A | 0.98 |
C6—C20 | 1.545 (2) | C24—H24B | 0.98 |
C6—C7 | 1.551 (2) | C24—H24C | 0.98 |
C7—C8 | 1.531 (3) | O6—C25 | 1.216 (4) |
C7—H7 | 1.00 | C25—C26 | 1.493 (5) |
C8—C9 | 1.549 (2) | C25—C28A | 1.507 (5) |
C8—H8A | 0.99 | C25—C28B | 1.566 (7) |
C8—H8B | 0.99 | C26—C27 | 1.519 (5) |
C9—C10 | 1.549 (2) | C26—H26A | 0.99 |
C9—C18 | 1.553 (3) | C26—H26B | 0.99 |
C9—H9 | 1.00 | C27—H27A | 0.98 |
C10—C20 | 1.512 (3) | C27—H27B | 0.98 |
C10—C11 | 1.532 (2) | C27—H27C | 0.98 |
C10—H10 | 1.00 | C28A—C29A | 1.512 (10) |
C11—C12 | 1.522 (3) | C28A—H28A | 0.99 |
C11—H11 | 1.00 | C28A—H28B | 0.99 |
C12—C13 | 1.539 (3) | C29A—H29A | 0.98 |
C12—H12A | 0.99 | C29A—H29B | 0.98 |
C12—H12B | 0.99 | C29A—H29C | 0.98 |
C13—C14 | 1.532 (3) | C28B—C29B | 1.531 (12) |
C13—C18 | 1.556 (3) | C28B—H28C | 0.99 |
C13—H13 | 1.00 | C28B—H28D | 0.99 |
C14—C15 | 1.513 (3) | C29B—H29D | 0.98 |
C14—H14A | 0.99 | C29B—H29E | 0.98 |
C14—H14B | 0.99 | C29B—H29F | 0.98 |
| | | |
C1—O1—H1 | 102 (3) | C16—C15—H15 | 109.7 |
C7—O3—H3 | 110.1 (18) | C15—C16—C17 | 110.16 (15) |
C11—O4—H4 | 110 (2) | C15—C16—H16A | 109.6 |
C15—O5—H5 | 108 (2) | C17—C16—H16A | 109.6 |
O2—C1—O1 | 123.3 (2) | C15—C16—H16B | 109.6 |
O2—C1—C2 | 124.76 (19) | C17—C16—H16B | 109.6 |
O1—C1—C2 | 111.94 (17) | H16A—C16—H16B | 108.1 |
C1—C2—C3 | 112.27 (17) | C16—C17—C18 | 114.91 (15) |
C1—C2—H2A | 109.2 | C16—C17—H17A | 108.5 |
C3—C2—H2A | 109.2 | C18—C17—H17A | 108.5 |
C1—C2—H2B | 109.2 | C16—C17—H17B | 108.5 |
C3—C2—H2B | 109.2 | C18—C17—H17B | 108.5 |
H2A—C2—H2B | 107.9 | H17A—C17—H17B | 107.5 |
C2—C3—C4 | 114.88 (16) | C19—C18—C17 | 106.18 (15) |
C2—C3—H3A | 108.5 | C19—C18—C9 | 111.55 (15) |
C4—C3—H3A | 108.5 | C17—C18—C9 | 112.66 (15) |
C2—C3—H3B | 108.5 | C19—C18—C13 | 108.94 (15) |
C4—C3—H3B | 108.5 | C17—C18—C13 | 107.34 (15) |
H3A—C3—H3B | 107.5 | C9—C18—C13 | 109.99 (15) |
C24—C4—C5 | 112.17 (15) | C18—C19—H19A | 109.5 |
C24—C4—C3 | 111.29 (17) | C18—C19—H19B | 109.5 |
C5—C4—C3 | 108.30 (15) | H19A—C19—H19B | 109.5 |
C24—C4—H4A | 108.3 | C18—C19—H19C | 109.5 |
C5—C4—H4A | 108.3 | H19A—C19—H19C | 109.5 |
C3—C4—H4A | 108.3 | H19B—C19—H19C | 109.5 |
C4—C5—C6 | 120.00 (15) | C10—C20—C21 | 116.68 (15) |
C4—C5—C22 | 111.09 (15) | C10—C20—C6 | 114.70 (15) |
C6—C5—C22 | 102.97 (15) | C21—C20—C6 | 104.34 (14) |
C4—C5—H5A | 107.4 | C10—C20—H20 | 106.8 |
C6—C5—H5A | 107.4 | C21—C20—H20 | 106.8 |
C22—C5—H5A | 107.4 | C6—C20—H20 | 106.8 |
C23—C6—C20 | 112.62 (15) | C20—C21—C22 | 103.65 (15) |
C23—C6—C7 | 109.12 (14) | C20—C21—H21A | 111.0 |
C20—C6—C7 | 106.72 (14) | C22—C21—H21A | 111.0 |
C23—C6—C5 | 109.88 (15) | C20—C21—H21B | 111.0 |
C20—C6—C5 | 99.58 (14) | C22—C21—H21B | 111.0 |
C7—C6—C5 | 118.64 (15) | H21A—C21—H21B | 109.0 |
O3—C7—C8 | 107.52 (14) | C21—C22—C5 | 107.16 (15) |
O3—C7—C6 | 112.12 (14) | C21—C22—H22A | 110.3 |
C8—C7—C6 | 111.33 (15) | C5—C22—H22A | 110.3 |
O3—C7—H7 | 108.6 | C21—C22—H22B | 110.3 |
C8—C7—H7 | 108.6 | C5—C22—H22B | 110.3 |
C6—C7—H7 | 108.6 | H22A—C22—H22B | 108.5 |
C7—C8—C9 | 115.26 (15) | C6—C23—H23A | 109.5 |
C7—C8—H8A | 108.5 | C6—C23—H23B | 109.5 |
C9—C8—H8A | 108.5 | H23A—C23—H23B | 109.5 |
C7—C8—H8B | 108.5 | C6—C23—H23C | 109.5 |
C9—C8—H8B | 108.5 | H23A—C23—H23C | 109.5 |
H8A—C8—H8B | 107.5 | H23B—C23—H23C | 109.5 |
C8—C9—C10 | 109.93 (14) | C4—C24—H24A | 109.5 |
C8—C9—C18 | 113.95 (15) | C4—C24—H24B | 109.5 |
C10—C9—C18 | 111.23 (14) | H24A—C24—H24B | 109.5 |
C8—C9—H9 | 107.1 | C4—C24—H24C | 109.5 |
C10—C9—H9 | 107.1 | H24A—C24—H24C | 109.5 |
C18—C9—H9 | 107.1 | H24B—C24—H24C | 109.5 |
C20—C10—C11 | 111.43 (15) | O6—C25—C26 | 123.0 (3) |
C20—C10—C9 | 110.51 (14) | O6—C25—C28A | 124.6 (3) |
C11—C10—C9 | 111.81 (14) | C26—C25—C28A | 111.2 (3) |
C20—C10—H10 | 107.6 | O6—C25—C28B | 111.1 (5) |
C11—C10—H10 | 107.6 | C26—C25—C28B | 122.8 (5) |
C9—C10—H10 | 107.6 | C25—C26—C27 | 115.1 (2) |
O4—C11—C12 | 112.81 (15) | C25—C26—H26A | 108.5 |
O4—C11—C10 | 107.84 (15) | C27—C26—H26A | 108.5 |
C12—C11—C10 | 111.06 (16) | C25—C26—H26B | 108.5 |
O4—C11—H11 | 108.3 | C27—C26—H26B | 108.5 |
C12—C11—H11 | 108.3 | H26A—C26—H26B | 107.5 |
C10—C11—H11 | 108.3 | C26—C27—H27A | 109.5 |
C11—C12—C13 | 114.33 (15) | C26—C27—H27B | 109.5 |
C11—C12—H12A | 108.7 | H27A—C27—H27B | 109.5 |
C13—C12—H12A | 108.7 | C26—C27—H27C | 109.5 |
C11—C12—H12B | 108.7 | H27A—C27—H27C | 109.5 |
C13—C12—H12B | 108.7 | H27B—C27—H27C | 109.5 |
H12A—C12—H12B | 107.6 | C25—C28A—C29A | 113.1 (7) |
C14—C13—C12 | 110.39 (15) | C25—C28A—H28A | 109.0 |
C14—C13—C18 | 113.39 (14) | C29A—C28A—H28A | 109.0 |
C12—C13—C18 | 112.17 (15) | C25—C28A—H28B | 109.0 |
C14—C13—H13 | 106.8 | C29A—C28A—H28B | 109.0 |
C12—C13—H13 | 106.8 | H28A—C28A—H28B | 107.8 |
C18—C13—H13 | 106.8 | C29B—C28B—C25 | 107.4 (8) |
C15—C14—C13 | 113.64 (16) | C29B—C28B—H28C | 110.2 |
C15—C14—H14A | 108.8 | C25—C28B—H28C | 110.2 |
C13—C14—H14A | 108.8 | C29B—C28B—H28D | 110.2 |
C15—C14—H14B | 108.8 | C25—C28B—H28D | 110.2 |
C13—C14—H14B | 108.8 | H28C—C28B—H28D | 108.5 |
H14A—C14—H14B | 107.7 | C28B—C29B—H29D | 109.5 |
O5—C15—C14 | 109.59 (16) | C28B—C29B—H29E | 109.5 |
O5—C15—C16 | 108.85 (15) | H29D—C29B—H29E | 109.5 |
C14—C15—C16 | 109.21 (15) | C28B—C29B—H29F | 109.5 |
O5—C15—H15 | 109.7 | H29D—C29B—H29F | 109.5 |
C14—C15—H15 | 109.7 | H29E—C29B—H29F | 109.5 |
| | | |
O2—C1—C2—C3 | −21.4 (3) | C14—C15—C16—C17 | −57.0 (2) |
O1—C1—C2—C3 | 157.19 (18) | C15—C16—C17—C18 | 58.4 (2) |
C1—C2—C3—C4 | 174.76 (18) | C16—C17—C18—C19 | −169.14 (16) |
C2—C3—C4—C24 | 61.3 (2) | C16—C17—C18—C9 | 68.5 (2) |
C2—C3—C4—C5 | −174.98 (17) | C16—C17—C18—C13 | −52.7 (2) |
C24—C4—C5—C6 | −60.7 (2) | C8—C9—C18—C19 | −59.65 (19) |
C3—C4—C5—C6 | 176.08 (16) | C10—C9—C18—C19 | 65.29 (18) |
C24—C4—C5—C22 | 179.25 (17) | C8—C9—C18—C17 | 59.65 (19) |
C3—C4—C5—C22 | 56.0 (2) | C10—C9—C18—C17 | −175.40 (14) |
C4—C5—C6—C23 | −46.1 (2) | C8—C9—C18—C13 | 179.35 (14) |
C22—C5—C6—C23 | 77.91 (17) | C10—C9—C18—C13 | −55.70 (17) |
C4—C5—C6—C20 | −164.52 (15) | C14—C13—C18—C19 | 163.94 (17) |
C22—C5—C6—C20 | −40.51 (16) | C12—C13—C18—C19 | −70.2 (2) |
C4—C5—C6—C7 | 80.4 (2) | C14—C13—C18—C17 | 49.4 (2) |
C22—C5—C6—C7 | −155.63 (15) | C12—C13—C18—C17 | 175.25 (16) |
C23—C6—C7—O3 | 172.37 (15) | C14—C13—C18—C9 | −73.51 (19) |
C20—C6—C7—O3 | −65.68 (19) | C12—C13—C18—C9 | 52.37 (19) |
C5—C6—C7—O3 | 45.5 (2) | C11—C10—C20—C21 | −53.6 (2) |
C23—C6—C7—C8 | −67.13 (18) | C9—C10—C20—C21 | −178.56 (14) |
C20—C6—C7—C8 | 54.82 (18) | C11—C10—C20—C6 | −176.03 (14) |
C5—C6—C7—C8 | 166.04 (14) | C9—C10—C20—C6 | 59.00 (18) |
O3—C7—C8—C9 | 69.17 (18) | C23—C6—C20—C10 | 59.83 (19) |
C6—C7—C8—C9 | −54.01 (19) | C7—C6—C20—C10 | −59.89 (19) |
C7—C8—C9—C10 | 50.4 (2) | C5—C6—C20—C10 | 176.19 (14) |
C7—C8—C9—C18 | 176.02 (14) | C23—C6—C20—C21 | −69.1 (2) |
C8—C9—C10—C20 | −50.60 (18) | C7—C6—C20—C21 | 171.23 (15) |
C18—C9—C10—C20 | −177.76 (14) | C5—C6—C20—C21 | 47.30 (17) |
C8—C9—C10—C11 | −175.35 (16) | C10—C20—C21—C22 | −162.53 (15) |
C18—C9—C10—C11 | 57.48 (19) | C6—C20—C21—C22 | −34.85 (19) |
C20—C10—C11—O4 | −54.32 (18) | C20—C21—C22—C5 | 8.5 (2) |
C9—C10—C11—O4 | 69.92 (19) | C4—C5—C22—C21 | 150.16 (16) |
C20—C10—C11—C12 | −178.40 (14) | C6—C5—C22—C21 | 20.46 (19) |
C9—C10—C11—C12 | −54.16 (19) | O6—C25—C26—C27 | 16.7 (5) |
O4—C11—C12—C13 | −69.58 (19) | C28A—C25—C26—C27 | −151.5 (4) |
C10—C11—C12—C13 | 51.6 (2) | C28B—C25—C26—C27 | 175.2 (5) |
C11—C12—C13—C14 | 76.0 (2) | O6—C25—C28A—C29A | 17.7 (9) |
C11—C12—C13—C18 | −51.5 (2) | C26—C25—C28A—C29A | −174.4 (6) |
C12—C13—C14—C15 | 178.72 (16) | C28B—C25—C28A—C29A | −55.7 (9) |
C18—C13—C14—C15 | −54.5 (2) | O6—C25—C28B—C29B | −66.6 (12) |
C13—C14—C15—O5 | 175.71 (15) | C26—C25—C28B—C29B | 132.7 (10) |
C13—C14—C15—C16 | 56.6 (2) | C28A—C25—C28B—C29B | 55.7 (12) |
O5—C15—C16—C17 | −176.63 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4i | 0.87 (3) | 1.84 (3) | 2.672 (2) | 160 (4) |
O3—H3···O2i | 0.83 (2) | 2.08 (2) | 2.879 (2) | 160 (2) |
O4—H4···O5ii | 0.86 (2) | 1.81 (2) | 2.6499 (19) | 165 (2) |
O5—H5···O3ii | 0.82 (2) | 2.10 (3) | 2.869 (2) | 157 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x, y−1/2, −z+1. |