Synthesis of modified bile acids <i>via</i> palladium-catalyzed C(sp<sup>3</sup>)-H (hetero)arylation.
Borade, Somnath Arjun; Naharwal, Sushma; Bhambri, Himanshi; Mandal, Sanjay K.; Bajaj, Kiran; Chitkara, Deepak; Sakhuja, Rajeev; Organic & biomolecular chemistry 21 (2023) 6719–6729; doi:10.1039/d3ob00916e

data_7159503
_publ_section_title
;
 Synthesis of modified bile acids <i>via</i> palladium-catalyzed
 C(sp<sup>3</sup>)-H (hetero)arylation.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6719
_journal_page_last               6729
_journal_paper_doi               10.1039/d3ob00916e
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C42 H56 N2 O4'
_chemical_formula_sum            'C42 H56 N2 O4'
_chemical_formula_weight         652.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-16 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2466(7)
_cell_length_b                   11.7371(8)
_cell_length_c                   33.379(3)
_cell_measurement_reflns_used    5710
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.395
_cell_measurement_theta_min      2.285
_cell_volume                     3622.6(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            23423
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_min         1.839
_diffrn_source                   Sealed-tube
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0538 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.9066.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         7340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.1286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                5377
_reflns_number_total             7340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00916e2.cif
_cod_data_source_block           3aa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159503.cif.
;
_cod_database_code               7159503
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C17C(H17C), C14C(H14C), C8C(H8C), C7C(H7C), C5C(H5C),
 C3C(H3C), C12C(H12C), C9C(H9C)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2B,H2C), C6C(H6CA,H6CB), C4C(H4CA,H4CB), C11C(H11A,H11B), C1C(H1CA,H1CB),
 C2C(H2CA,H2CB), C16C(H16A,H16B), C15C(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C6B(H6B), C5B(H5BA), C4B(H4B), C3B(H3B), C2B(H2BA),
 C7A(H7A), C6A(H6A), C5A(H5AA), C1A(H1A)
2.d Idealised Me refined as rotating group:
 C21C(H21A,H21B,H21C), C20C(H20A,H20B,H20C), C19C(H19A,H19B,H19C), C18C(H18A,
 H18B,H18C), C5(H5A,H5B,H5D), C22C(H22A,H22B,H22C)
;
_shelx_res_checksum              22271
_olex2_submission_special_instructions 'No special instructions were received'