Synthesis of 12β-methyl-18-<i>nor</i>-avicholic acid analogues as potential TGR5 agonists.
Ure, Elizabeth M.; Harris, Lawrence D.; Cameron, Scott A.; Weymouth-Wilson, Alex; Furneaux, Richard H.; Pitman, Janet L.; Hinkley, Simon F.; Luxenburger, Andreas; Organic & biomolecular chemistry 20 (2022) 3511–3527; doi:10.1039/d1ob02401a

data_7158531
_publ_section_title
;
 Synthesis of 12\b-methyl-18-<i>nor</i>-avicholic acid analogues as
 potential TGR5 agonists.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3511
_journal_page_last               3527
_journal_paper_doi               10.1039/d1ob02401a
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C25 H42 O4'
_chemical_formula_weight         406.58
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_symmetry_cell_setting           hexagonal
_symmetry_Int_Tables_number      170
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_update_record
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   32.26794(16)
_cell_length_b                   32.26794(16)
_cell_length_c                   6.19392(4)
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_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.455
_cell_measurement_theta_min      4.176
_cell_volume                     5585.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0856
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0015109
_diffrn_orient_matrix_UB_12      -0.0484365
_diffrn_orient_matrix_UB_13      -0.0099368
_diffrn_orient_matrix_UB_21      -0.0533667
_diffrn_orient_matrix_UB_22      -0.0249247
_diffrn_orient_matrix_UB_23      -0.0618232
_diffrn_orient_matrix_UB_31      0.0137481
_diffrn_orient_matrix_UB_32      0.0083782
_diffrn_orient_matrix_UB_33      -0.2407367
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            70968
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.295
_diffrn_reflns_theta_min         4.186
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.344
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.725
_exptl_crystal_description       rod
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.616
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.018
_refine_ls_abs_structure_details
;
 Flack x determined using 2701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         6921
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.3359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0634
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                6784
_reflns_number_total             6921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02401a2.cif
_cod_data_source_block           46-emu-066-sq
_cod_depositor_comments
'Adding full bibliography for 7158525--7158531.cif.'
_cod_database_code               7158531
_shelx_estimated_absorpt_t_min   0.802
_shelx_estimated_absorpt_t_max   0.955
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              31884
_shelx_hkl_checksum              8032
_shelx_fab_checksum              43833