##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     from_SHELX97
_journal_date_recd_electronic     2011-03-14
_journal_date_accepted     2011-05-04
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2011
_journal_volume     67
_journal_issue      6
_journal_page_first     o206
_journal_page_last     o208
_journal_paper_category     FO
_journal_coeditor_code     BI3016
_publ_contact_author_name     'Ulli Englert'
_publ_contact_author_address
;
      Institut fuer Anorganische Chemie
      RWTH Aachen
      Landoltweg 1
      52074 Aachen
      Germany
;
_publ_contact_author_email     ullrich.englert@ac.rwth-aachen.de
_publ_contact_author_fax     '0049-241-8092288'
_publ_contact_author_phone     '0049-241-8090074'
_publ_section_title
;
The molecular conformation of pentan-3-one studied in cholic acid pentan-3-one
solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Kalf, Irmgard'
;     Institute of Inorganic Chemistry
         RWTH Aachen University
         Landoltweg 1
         52074 Aachen
         Germany
;
    'Englert, Ulli'
;     Institute of Inorganic Chemistry
         RWTH Aachen University
         Landoltweg 1
         52074 Aachen
         Germany
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
cholic acid--pentan-3-one (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H10 O, C24 H40 O5'
_chemical_formula_sum     'C29 H50 O6'
_chemical_formula_iupac     'C5 H10 O, C24 H40 O5'
_chemical_formula_weight     494.69
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     12.5606(7)
_cell_length_b     8.0425(5)
_cell_length_c     13.9139(8)
_cell_angle_alpha     90.00
_cell_angle_beta     102.002(3)
_cell_angle_gamma     90.00
_cell_volume     1374.84(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4097
_cell_measurement_theta_min     2.45
_cell_measurement_theta_max     29.12
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'fragment'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.195
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     544
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Incoatec microsource'
_diffrn_radiation_monochromator     'multilayer optics'
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     33615
_diffrn_reflns_av_R_equivalents     0.0697
_diffrn_reflns_av_sigmaI/netI     0.0960
_diffrn_reflns_theta_min     1.66
_diffrn_reflns_theta_max     40.35
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.846
_diffrn_measured_fraction_theta_full     0.968
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
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.
;
_reflns_number_total     13745
_reflns_number_gt     9042
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1284
_refine_ls_R_factor_gt     0.0805
_refine_ls_wR_factor_gt     0.1770
_refine_ls_wR_factor_ref     0.1998
_refine_ls_goodness_of_fit_ref     1.064
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     13745
_refine_ls_number_parameters     357
_refine_ls_number_restraints     26
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0850P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.694
_refine_diff_density_min     -0.442
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
;
;
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.69836(14) 0.71124(18) 1.27098(11) 0.0233(3) Uani d D 1 1 . .
    H H1 0.762(2) 0.670(5) 1.270(3) 0.058(11) Uiso d D 1 1 . .
    O O2 0.66149(14) 0.46199(19) 1.20162(12) 0.0265(3) Uani d . 1 1 . .
    O O3 0.19334(13) 0.68117(17) 0.77718(10) 0.0187(3) Uani d D 1 1 . .
    H H3 0.2435(18) 0.749(3) 0.7951(19) 0.020(6) Uiso d D 1 1 . .
    O O4 0.08920(12) 0.14850(16) 0.70817(10) 0.0183(3) Uani d D 1 1 . .
    H H4 0.086(2) 0.052(2) 0.682(2) 0.028(7) Uiso d D 1 1 . .
    O O5 -0.09985(14) 0.37263(17) 0.39354(10) 0.0210(3) Uani d D 1 1 . .
    H H5 -0.131(2) 0.300(3) 0.3570(19) 0.028(7) Uiso d D 1 1 . .
    C C1 0.63263(18) 0.6008(2) 1.21892(14) 0.0198(4) Uani d . 1 1 . .
    C C2 0.51952(19) 0.6700(3) 1.18229(16) 0.0269(4) Uani d . 1 1 . .
    H H2A 0.5250 0.7889 1.1655 0.032 Uiso calc R 1 1 . .
    H H2B 0.4782 0.6627 1.2355 0.032 Uiso calc R 1 1 . .
    C C3 0.45794(18) 0.5775(3) 1.09263(15) 0.0205(4) Uani d . 1 1 . .
    H H3A 0.4595 0.4572 1.1079 0.025 Uiso calc R 1 1 . .
    H H3B 0.4966 0.5935 1.0382 0.025 Uiso calc R 1 1 . .
    C C4 0.33861(16) 0.6315(2) 1.05719(13) 0.0168(3) Uani d . 1 1 . .
    H H4A 0.3000 0.6163 1.1126 0.020 Uiso calc R 1 1 . .
    C C5 0.28543(17) 0.5161(2) 0.97245(13) 0.0161(3) Uani d . 1 1 . .
    H H5A 0.3262 0.5302 0.9184 0.019 Uiso calc R 1 1 . .
    C C6 0.16201(16) 0.5336(2) 0.92592(13) 0.0145(3) Uani d . 1 1 . .
    C C7 0.12530(16) 0.6728(2) 0.84903(13) 0.0153(3) Uani d . 1 1 . .
    H H7 0.1294 0.7819 0.8841 0.018 Uiso calc R 1 1 . .
    C C8 0.00800(16) 0.6458(2) 0.79326(13) 0.0162(3) Uani d . 1 1 . .
    H H8A -0.0099 0.7324 0.7418 0.019 Uiso calc R 1 1 . .
    H H8B -0.0412 0.6618 0.8396 0.019 Uiso calc R 1 1 . .
    C C9 -0.01560(16) 0.4732(2) 0.74399(13) 0.0140(3) Uani d . 1 1 . .
    H H9 0.0275 0.4659 0.6913 0.017 Uiso calc R 1 1 . .
    C C10 0.02636(17) 0.3340(2) 0.81938(13) 0.0158(3) Uani d . 1 1 . .
    H H10 -0.0188 0.3369 0.8707 0.019 Uiso calc R 1 1 . .
    C C11 0.01322(17) 0.1614(2) 0.77187(13) 0.0166(3) Uani d . 1 1 . .
    H H11 0.0327 0.0762 0.8250 0.020 Uiso calc R 1 1 . .
    C C12 -0.10390(18) 0.1316(2) 0.71865(14) 0.0193(4) Uani d . 1 1 . .
    H H12A -0.1498 0.1199 0.7681 0.023 Uiso calc R 1 1 . .
    H H12B -0.1074 0.0252 0.6823 0.023 Uiso calc R 1 1 . .
    C C13 -0.15184(16) 0.2700(2) 0.64605(13) 0.0160(3) Uani d . 1 1 . .
    H H13 -0.2320 0.2494 0.6269 0.019 Uiso calc R 1 1 . .
    C C14 -0.10709(17) 0.2569(2) 0.55196(13) 0.0168(3) Uani d . 1 1 . .
    H H14A -0.0269 0.2680 0.5692 0.020 Uiso calc R 1 1 . .
    H H14B -0.1242 0.1452 0.5230 0.020 Uiso calc R 1 1 . .
    C C15 -0.15237(17) 0.3868(2) 0.47568(13) 0.0171(3) Uani d . 1 1 . .
    H H15 -0.2326 0.3704 0.4530 0.021 Uiso calc R 1 1 . .
    C C16 -0.12999(17) 0.5590(2) 0.52070(14) 0.0179(3) Uani d . 1 1 . .
    H H16A -0.1620 0.6444 0.4720 0.022 Uiso calc R 1 1 . .
    H H16B -0.0505 0.5781 0.5388 0.022 Uiso calc R 1 1 . .
    C C17 -0.17912(17) 0.5745(2) 0.61221(14) 0.0183(3) Uani d . 1 1 . .
    H H17A -0.2591 0.5632 0.5921 0.022 Uiso calc R 1 1 . .
    H H17B -0.1636 0.6875 0.6399 0.022 Uiso calc R 1 1 . .
    C C18 -0.13689(16) 0.4454(2) 0.69420(13) 0.0157(3) Uani d . 1 1 . .
    C C19 -0.21174(18) 0.4604(3) 0.76871(15) 0.0227(4) Uani d . 1 1 . .
    H H19A -0.1842 0.3890 0.8255 0.034 Uiso calc R 1 1 . .
    H H19B -0.2856 0.4257 0.7375 0.034 Uiso calc R 1 1 . .
    H H19C -0.2130 0.5762 0.7905 0.034 Uiso calc R 1 1 . .
    C C20 0.14312(16) 0.3667(2) 0.87001(13) 0.0149(3) Uani d . 1 1 . .
    H H20 0.1866 0.3707 0.8175 0.018 Uiso calc R 1 1 . .
    C C21 0.19700(18) 0.2374(2) 0.94500(14) 0.0193(4) Uani d . 1 1 . .
    H H21A 0.2198 0.1385 0.9119 0.023 Uiso calc R 1 1 . .
    H H21B 0.1470 0.2017 0.9875 0.023 Uiso calc R 1 1 . .
    C C22 0.29609(18) 0.3295(2) 1.00487(15) 0.0205(4) Uani d . 1 1 . .
    H H22A 0.3643 0.2814 0.9918 0.025 Uiso calc R 1 1 . .
    H H22B 0.2973 0.3197 1.0760 0.025 Uiso calc R 1 1 . .
    C C23 0.09651(17) 0.5475(2) 1.00720(14) 0.0182(4) Uani d . 1 1 . .
    H H23A 0.1223 0.4638 1.0579 0.027 Uiso calc R 1 1 . .
    H H23B 0.0192 0.5287 0.9791 0.027 Uiso calc R 1 1 . .
    H H23C 0.1062 0.6587 1.0365 0.027 Uiso calc R 1 1 . .
    C C24 0.33062(19) 0.8150(2) 1.02697(15) 0.0221(4) Uani d . 1 1 . .
    H H24A 0.3663 0.8317 0.9714 0.033 Uiso calc R 1 1 . .
    H H24B 0.3666 0.8837 1.0825 0.033 Uiso calc R 1 1 . .
    H H24C 0.2539 0.8471 1.0077 0.033 Uiso calc R 1 1 . .
    O O6 0.46564(18) -0.0848(3) 0.38832(16) 0.0496(6) Uani d . 1 1 A .
    C C25 0.5509(2) -0.0080(5) 0.4042(2) 0.0446(7) Uani d DU 1 1 . .
    C C26 0.5881(2) 0.0944(3) 0.3280(3) 0.0416(7) Uani d . 1 1 A .
    H H26A 0.6470 0.0337 0.3055 0.050 Uiso calc R 1 1 . .
    H H26B 0.6196 0.1992 0.3589 0.050 Uiso calc R 1 1 . .
    C C27 0.5002(2) 0.1373(4) 0.2388(2) 0.0431(7) Uani d . 1 1 . .
    H H27A 0.4647 0.0350 0.2102 0.065 Uiso calc R 1 1 A .
    H H27B 0.5331 0.1944 0.1900 0.065 Uiso calc R 1 1 . .
    H H27C 0.4461 0.2101 0.2588 0.065 Uiso calc R 1 1 . .
    C C28A 0.6190(5) 0.0254(8) 0.5050(3) 0.0383(15) Uani d PDU 0.544(12) 1 A 1
    H H28A 0.6083 0.1424 0.5230 0.046 Uiso calc PR 0.544(12) 1 A 1
    H H28B 0.6968 0.0110 0.5029 0.046 Uiso calc PR 0.544(12) 1 A 1
    C C29A 0.5915(13) -0.0875(14) 0.5832(8) 0.047(2) Uani d PDU 0.544(12) 1 A 1
    H H29A 0.5161 -0.0682 0.5890 0.070 Uiso calc PR 0.544(12) 1 A 1
    H H29B 0.6405 -0.0639 0.6463 0.070 Uiso calc PR 0.544(12) 1 A 1
    H H29C 0.6001 -0.2037 0.5650 0.070 Uiso calc PR 0.544(12) 1 A 1
    C C28B 0.6306(7) -0.0765(15) 0.4975(6) 0.062(2) Uani d PDU 0.456(12) 1 A 2
    H H28C 0.6404 -0.1979 0.4915 0.075 Uiso calc PR 0.456(12) 1 A 2
    H H28D 0.7026 -0.0222 0.5051 0.075 Uiso calc PR 0.456(12) 1 A 2
    C C29B 0.5804(18) -0.038(2) 0.5864(10) 0.062(3) Uani d PDU 0.456(12) 1 A 2
    H H29D 0.5487 0.0735 0.5796 0.093 Uiso calc PR 0.456(12) 1 A 2
    H H29E 0.6370 -0.0440 0.6466 0.093 Uiso calc PR 0.456(12) 1 A 2
    H H29F 0.5235 -0.1200 0.5899 0.093 Uiso calc PR 0.456(12) 1 A 2
_geom_special_details
;
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.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . 1.321(2) yes
    O1 H1 . 0.863(18) ?
    O2 C1 . 1.213(2) yes
    O3 C7 . 1.446(2) yes
    O3 H3 . 0.829(17) ?
    O4 C11 . 1.435(2) yes
    O4 H4 . 0.853(17) ?
    O5 C15 . 1.438(2) yes
    O5 H5 . 0.819(17) ?
    C1 C2 . 1.512(3) yes
    C2 C3 . 1.519(3) yes
    C2 H2A . 0.99 ?
    C2 H2B . 0.99 ?
    C3 C4 . 1.540(3) yes
    C3 H3A . 0.99 ?
    C3 H3B . 0.99 ?
    C4 C24 . 1.533(3) ?
    C4 C5 . 1.539(3) ?
    C4 H4A . 1.00 ?
    C5 C6 . 1.557(3) ?
    C5 C22 . 1.565(3) ?
    C5 H5A . 1.00 ?
    C6 C23 . 1.535(3) ?
    C6 C20 . 1.545(2) ?
    C6 C7 . 1.551(2) ?
    C7 C8 . 1.531(3) ?
    C7 H7 . 1.00 ?
    C8 C9 . 1.549(2) ?
    C8 H8A . 0.99 ?
    C8 H8B . 0.99 ?
    C9 C10 . 1.549(2) ?
    C9 C18 . 1.553(3) ?
    C9 H9 . 1.00 ?
    C10 C20 . 1.512(3) ?
    C10 C11 . 1.532(2) ?
    C10 H10 . 1.00 ?
    C11 C12 . 1.522(3) ?
    C11 H11 . 1.00 ?
    C12 C13 . 1.539(3) ?
    C12 H12A . 0.99 ?
    C12 H12B . 0.99 ?
    C13 C14 . 1.532(3) ?
    C13 C18 . 1.556(3) ?
    C13 H13 . 1.00 ?
    C14 C15 . 1.513(3) ?
    C14 H14A . 0.99 ?
    C14 H14B . 0.99 ?
    C15 C16 . 1.522(2) ?
    C15 H15 . 1.00 ?
    C16 C17 . 1.531(3) ?
    C16 H16A . 0.99 ?
    C16 H16B . 0.99 ?
    C17 C18 . 1.552(3) ?
    C17 H17A . 0.99 ?
    C17 H17B . 0.99 ?
    C18 C19 . 1.542(3) ?
    C19 H19A . 0.98 ?
    C19 H19B . 0.98 ?
    C19 H19C . 0.98 ?
    C20 C21 . 1.528(2) ?
    C20 H20 . 1.00 ?
    C21 C22 . 1.536(3) ?
    C21 H21A . 0.99 ?
    C21 H21B . 0.99 ?
    C22 H22A . 0.99 ?
    C22 H22B . 0.99 ?
    C23 H23A . 0.98 ?
    C23 H23B . 0.98 ?
    C23 H23C . 0.98 ?
    C24 H24A . 0.98 ?
    C24 H24B . 0.98 ?
    C24 H24C . 0.98 ?
    O6 C25 . 1.216(4) yes
    C25 C26 . 1.493(5) yes
    C25 C28A . 1.507(5) yes
    C25 C28B . 1.566(7) yes
    C26 C27 . 1.519(5) yes
    C26 H26A . 0.99 ?
    C26 H26B . 0.99 ?
    C27 H27A . 0.98 ?
    C27 H27B . 0.98 ?
    C27 H27C . 0.98 ?
    C28A C29A . 1.512(10) yes
    C28A H28A . 0.99 ?
    C28A H28B . 0.99 ?
    C29A H29A . 0.98 ?
    C29A H29B . 0.98 ?
    C29A H29C . 0.98 ?
    C28B C29B . 1.531(12) yes
    C28B H28C . 0.99 ?
    C28B H28D . 0.99 ?
    C29B H29D . 0.98 ?
    C29B H29E . 0.98 ?
    C29B H29F . 0.98 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 O1 H1 . . 102(3) ?
    C7 O3 H3 . . 110.1(18) ?
    C11 O4 H4 . . 110(2) ?
    C15 O5 H5 . . 108(2) ?
    O2 C1 O1 . . 123.3(2) ?
    O2 C1 C2 . . 124.76(19) ?
    O1 C1 C2 . . 111.94(17) ?
    C1 C2 C3 . . 112.27(17) ?
    C1 C2 H2A . . 109.2 ?
    C3 C2 H2A . . 109.2 ?
    C1 C2 H2B . . 109.2 ?
    C3 C2 H2B . . 109.2 ?
    H2A C2 H2B . . 107.9 ?
    C2 C3 C4 . . 114.88(16) ?
    C2 C3 H3A . . 108.5 ?
    C4 C3 H3A . . 108.5 ?
    C2 C3 H3B . . 108.5 ?
    C4 C3 H3B . . 108.5 ?
    H3A C3 H3B . . 107.5 ?
    C24 C4 C5 . . 112.17(15) ?
    C24 C4 C3 . . 111.29(17) ?
    C5 C4 C3 . . 108.30(15) ?
    C24 C4 H4A . . 108.3 ?
    C5 C4 H4A . . 108.3 ?
    C3 C4 H4A . . 108.3 ?
    C4 C5 C6 . . 120.00(15) ?
    C4 C5 C22 . . 111.09(15) ?
    C6 C5 C22 . . 102.97(15) ?
    C4 C5 H5A . . 107.4 ?
    C6 C5 H5A . . 107.4 ?
    C22 C5 H5A . . 107.4 ?
    C23 C6 C20 . . 112.62(15) ?
    C23 C6 C7 . . 109.12(14) ?
    C20 C6 C7 . . 106.72(14) ?
    C23 C6 C5 . . 109.88(15) ?
    C20 C6 C5 . . 99.58(14) ?
    C7 C6 C5 . . 118.64(15) ?
    O3 C7 C8 . . 107.52(14) ?
    O3 C7 C6 . . 112.12(14) ?
    C8 C7 C6 . . 111.33(15) ?
    O3 C7 H7 . . 108.6 ?
    C8 C7 H7 . . 108.6 ?
    C6 C7 H7 . . 108.6 ?
    C7 C8 C9 . . 115.26(15) ?
    C7 C8 H8A . . 108.5 ?
    C9 C8 H8A . . 108.5 ?
    C7 C8 H8B . . 108.5 ?
    C9 C8 H8B . . 108.5 ?
    H8A C8 H8B . . 107.5 ?
    C8 C9 C10 . . 109.93(14) ?
    C8 C9 C18 . . 113.95(15) ?
    C10 C9 C18 . . 111.23(14) ?
    C8 C9 H9 . . 107.1 ?
    C10 C9 H9 . . 107.1 ?
    C18 C9 H9 . . 107.1 ?
    C20 C10 C11 . . 111.43(15) ?
    C20 C10 C9 . . 110.51(14) ?
    C11 C10 C9 . . 111.81(14) ?
    C20 C10 H10 . . 107.6 ?
    C11 C10 H10 . . 107.6 ?
    C9 C10 H10 . . 107.6 ?
    O4 C11 C12 . . 112.81(15) ?
    O4 C11 C10 . . 107.84(15) ?
    C12 C11 C10 . . 111.06(16) ?
    O4 C11 H11 . . 108.3 ?
    C12 C11 H11 . . 108.3 ?
    C10 C11 H11 . . 108.3 ?
    C11 C12 C13 . . 114.33(15) ?
    C11 C12 H12A . . 108.7 ?
    C13 C12 H12A . . 108.7 ?
    C11 C12 H12B . . 108.7 ?
    C13 C12 H12B . . 108.7 ?
    H12A C12 H12B . . 107.6 ?
    C14 C13 C12 . . 110.39(15) ?
    C14 C13 C18 . . 113.39(14) ?
    C12 C13 C18 . . 112.17(15) ?
    C14 C13 H13 . . 106.8 ?
    C12 C13 H13 . . 106.8 ?
    C18 C13 H13 . . 106.8 ?
    C15 C14 C13 . . 113.64(16) ?
    C15 C14 H14A . . 108.8 ?
    C13 C14 H14A . . 108.8 ?
    C15 C14 H14B . . 108.8 ?
    C13 C14 H14B . . 108.8 ?
    H14A C14 H14B . . 107.7 ?
    O5 C15 C14 . . 109.59(16) ?
    O5 C15 C16 . . 108.85(15) ?
    C14 C15 C16 . . 109.21(15) ?
    O5 C15 H15 . . 109.7 ?
    C14 C15 H15 . . 109.7 ?
    C16 C15 H15 . . 109.7 ?
    C15 C16 C17 . . 110.16(15) ?
    C15 C16 H16A . . 109.6 ?
    C17 C16 H16A . . 109.6 ?
    C15 C16 H16B . . 109.6 ?
    C17 C16 H16B . . 109.6 ?
    H16A C16 H16B . . 108.1 ?
    C16 C17 C18 . . 114.91(15) ?
    C16 C17 H17A . . 108.5 ?
    C18 C17 H17A . . 108.5 ?
    C16 C17 H17B . . 108.5 ?
    C18 C17 H17B . . 108.5 ?
    H17A C17 H17B . . 107.5 ?
    C19 C18 C17 . . 106.18(15) ?
    C19 C18 C9 . . 111.55(15) ?
    C17 C18 C9 . . 112.66(15) ?
    C19 C18 C13 . . 108.94(15) ?
    C17 C18 C13 . . 107.34(15) ?
    C9 C18 C13 . . 109.99(15) ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C10 C20 C21 . . 116.68(15) ?
    C10 C20 C6 . . 114.70(15) ?
    C21 C20 C6 . . 104.34(14) ?
    C10 C20 H20 . . 106.8 ?
    C21 C20 H20 . . 106.8 ?
    C6 C20 H20 . . 106.8 ?
    C20 C21 C22 . . 103.65(15) ?
    C20 C21 H21A . . 111.0 ?
    C22 C21 H21A . . 111.0 ?
    C20 C21 H21B . . 111.0 ?
    C22 C21 H21B . . 111.0 ?
    H21A C21 H21B . . 109.0 ?
    C21 C22 C5 . . 107.16(15) ?
    C21 C22 H22A . . 110.3 ?
    C5 C22 H22A . . 110.3 ?
    C21 C22 H22B . . 110.3 ?
    C5 C22 H22B . . 110.3 ?
    H22A C22 H22B . . 108.5 ?
    C6 C23 H23A . . 109.5 ?
    C6 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C6 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C4 C24 H24A . . 109.5 ?
    C4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    O6 C25 C26 . . 123.0(3) yes
    O6 C25 C28A . . 124.6(3) yes
    C26 C25 C28A . . 111.2(3) yes
    O6 C25 C28B . . 111.1(5) yes
    C26 C25 C28B . . 122.8(5) yes
    C25 C26 C27 . . 115.1(2) yes
    C25 C26 H26A . . 108.5 ?
    C27 C26 H26A . . 108.5 ?
    C25 C26 H26B . . 108.5 ?
    C27 C26 H26B . . 108.5 ?
    H26A C26 H26B . . 107.5 ?
    C26 C27 H27A . . 109.5 ?
    C26 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    C26 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C25 C28A C29A . . 113.1(7) yes
    C25 C28A H28A . . 109.0 ?
    C29A C28A H28A . . 109.0 ?
    C25 C28A H28B . . 109.0 ?
    C29A C28A H28B . . 109.0 ?
    H28A C28A H28B . . 107.8 ?
    C29B C28B C25 . . 107.4(8) yes
    C29B C28B H28C . . 110.2 ?
    C25 C28B H28C . . 110.2 ?
    C29B C28B H28D . . 110.2 ?
    C25 C28B H28D . . 110.2 ?
    H28C C28B H28D . . 108.5 ?
    C28B C29B H29D . . 109.5 ?
    C28B C29B H29E . . 109.5 ?
    H29D C29B H29E . . 109.5 ?
    C28B C29B H29F . . 109.5 ?
    H29D C29B H29F . . 109.5 ?
    H29E C29B H29F . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O2 C1 C2 C3 . . . . -21.4(3) ?
    O1 C1 C2 C3 . . . . 157.19(18) ?
    C1 C2 C3 C4 . . . . 174.76(18) ?
    C2 C3 C4 C24 . . . . 61.3(2) ?
    C2 C3 C4 C5 . . . . -174.98(17) ?
    C24 C4 C5 C6 . . . . -60.7(2) ?
    C3 C4 C5 C6 . . . . 176.08(16) ?
    C24 C4 C5 C22 . . . . 179.25(17) ?
    C3 C4 C5 C22 . . . . 56.0(2) ?
    C4 C5 C6 C23 . . . . -46.1(2) ?
    C22 C5 C6 C23 . . . . 77.91(17) ?
    C4 C5 C6 C20 . . . . -164.52(15) ?
    C22 C5 C6 C20 . . . . -40.51(16) ?
    C4 C5 C6 C7 . . . . 80.4(2) ?
    C22 C5 C6 C7 . . . . -155.63(15) ?
    C23 C6 C7 O3 . . . . 172.37(15) ?
    C20 C6 C7 O3 . . . . -65.68(19) ?
    C5 C6 C7 O3 . . . . 45.5(2) ?
    C23 C6 C7 C8 . . . . -67.13(18) ?
    C20 C6 C7 C8 . . . . 54.82(18) ?
    C5 C6 C7 C8 . . . . 166.04(14) ?
    O3 C7 C8 C9 . . . . 69.17(18) ?
    C6 C7 C8 C9 . . . . -54.01(19) ?
    C7 C8 C9 C10 . . . . 50.4(2) ?
    C7 C8 C9 C18 . . . . 176.02(14) ?
    C8 C9 C10 C20 . . . . -50.60(18) ?
    C18 C9 C10 C20 . . . . -177.76(14) ?
    C8 C9 C10 C11 . . . . -175.35(16) ?
    C18 C9 C10 C11 . . . . 57.48(19) ?
    C20 C10 C11 O4 . . . . -54.32(18) ?
    C9 C10 C11 O4 . . . . 69.92(19) ?
    C20 C10 C11 C12 . . . . -178.40(14) ?
    C9 C10 C11 C12 . . . . -54.16(19) ?
    O4 C11 C12 C13 . . . . -69.58(19) ?
    C10 C11 C12 C13 . . . . 51.6(2) ?
    C11 C12 C13 C14 . . . . 76.0(2) ?
    C11 C12 C13 C18 . . . . -51.5(2) ?
    C12 C13 C14 C15 . . . . 178.72(16) ?
    C18 C13 C14 C15 . . . . -54.5(2) ?
    C13 C14 C15 O5 . . . . 175.71(15) ?
    C13 C14 C15 C16 . . . . 56.6(2) ?
    O5 C15 C16 C17 . . . . -176.63(16) ?
    C14 C15 C16 C17 . . . . -57.0(2) ?
    C15 C16 C17 C18 . . . . 58.4(2) ?
    C16 C17 C18 C19 . . . . -169.14(16) ?
    C16 C17 C18 C9 . . . . 68.5(2) ?
    C16 C17 C18 C13 . . . . -52.7(2) ?
    C8 C9 C18 C19 . . . . -59.65(19) ?
    C10 C9 C18 C19 . . . . 65.29(18) ?
    C8 C9 C18 C17 . . . . 59.65(19) ?
    C10 C9 C18 C17 . . . . -175.40(14) ?
    C8 C9 C18 C13 . . . . 179.35(14) ?
    C10 C9 C18 C13 . . . . -55.70(17) ?
    C14 C13 C18 C19 . . . . 163.94(17) ?
    C12 C13 C18 C19 . . . . -70.2(2) ?
    C14 C13 C18 C17 . . . . 49.4(2) ?
    C12 C13 C18 C17 . . . . 175.25(16) ?
    C14 C13 C18 C9 . . . . -73.51(19) ?
    C12 C13 C18 C9 . . . . 52.37(19) ?
    C11 C10 C20 C21 . . . . -53.6(2) ?
    C9 C10 C20 C21 . . . . -178.56(14) ?
    C11 C10 C20 C6 . . . . -176.03(14) ?
    C9 C10 C20 C6 . . . . 59.00(18) ?
    C23 C6 C20 C10 . . . . 59.83(19) ?
    C7 C6 C20 C10 . . . . -59.89(19) ?
    C5 C6 C20 C10 . . . . 176.19(14) ?
    C23 C6 C20 C21 . . . . -69.1(2) ?
    C7 C6 C20 C21 . . . . 171.23(15) ?
    C5 C6 C20 C21 . . . . 47.30(17) ?
    C10 C20 C21 C22 . . . . -162.53(15) ?
    C6 C20 C21 C22 . . . . -34.85(19) ?
    C20 C21 C22 C5 . . . . 8.5(2) ?
    C4 C5 C22 C21 . . . . 150.16(16) ?
    C6 C5 C22 C21 . . . . 20.46(19) ?
    O6 C25 C26 C27 . . . . 16.7(5) yes
    C28A C25 C26 C27 . . . . -151.5(4) ?
    C28B C25 C26 C27 . . . . 175.2(5) ?
    O6 C25 C28A C29A . . . . 17.7(9) yes
    C26 C25 C28A C29A . . . . -174.4(6) ?
    C28B C25 C28A C29A . . . . -55.7(9) ?
    O6 C25 C28B C29B . . . . -66.6(12) yes
    C26 C25 C28B C29B . . . . 132.7(10) ?
    C28A C25 C28B C29B . . . . 55.7(12) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O1 H1 O4 2_657 0.87(3) 1.84(3) 2.672(2) 160(4) yes
    O3 H3 O2 2_657 0.83(2) 2.08(2) 2.879(2) 160(2) yes
    O4 H4 O5 2_546 0.855(18) 1.81(2) 2.6499(19) 165(2) yes
    O5 H5 O3 2_546 0.82(2) 2.10(3) 2.869(2) 157(2) yes
