Structural determination of oleanane-28,13β-olide and taraxerane-28,14β-olide fluorolactonization products from the reaction of oleanolic acid with SelectfluorTM
Eadsforth, Megan A.; Kong, Linghan; Whitehead, George; Vitórica-Yrezábal, Iñigo J.; O'Keefe, Raymond T.; Bryce, Richard A.; Whitehead, Roger C.; Acta Crystallographica Section E Crystallographic Communications 80 (2024) –; doi:10.1107/S2056989024006480

data_2023200
_publ_section_title
;
 Structural determination of oleanane-28,13\b-olide and
 taraxerane-28,14\b-olide fluorolactonization products from the reaction
 of oleanolic acid with SelectfluorTM
;
_journal_coeditor_code           YY2009
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024006480
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_iupac          '2C30 H47 F O3, C H4 O'
_chemical_formula_moiety         '2(C30 H47 F O3), C H4 O'
_chemical_formula_sum            'C61 H98 F2 O7'
_chemical_formula_weight         981.39
_chemical_name_systematic
;
12-\a-Fluoro-3\b-hydroxyolean-28,13\b-olide methanol hemisolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1762(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4983(2)
_cell_length_b                   7.17223(12)
_cell_length_c                   60.3774(12)
_cell_measurement_reflns_used    13347
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6780
_cell_measurement_theta_min      1.5070
_cell_volume                     5397.90(17)
_computing_cell_refinement
;
CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al., 20096)
;
_computing_structure_refinement
;
<i>SHELXL2019/3</i> (Sheldrick, 2015bb)
;
_computing_structure_solution
;
<i>SHELXT</i>  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       75
_diffrn_reflns_limit_l_min       -74
_diffrn_reflns_number            77709
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.154
_diffrn_reflns_theta_min         2.201
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       plate
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.541
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 7081 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1292
_refine_ls_number_reflns         21225
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1319P)^2^+16.8795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2713
_refine_ls_wR_factor_ref         0.2766
_reflns_number_gt                19142
_reflns_number_total             21225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yy2009.cif
_cod_data_source_block           1
_cod_database_code               2023200
_shelx_estimated_absorpt_t_min   0.775
_shelx_estimated_absorpt_t_max   0.966
_shelx_hkl_checksum              39846
_shelx_res_checksum              51689