Rhodium-catalyzed double hydroboration of pyridine: the origin of the chemo- and regioselectivities
Choi, Hyoju; Wang, Ruibin; Kim, Suyeon; Kim, Dongwook; Baik, Mu-Hyun; Park, Sehoon; Catalysis Science & Technology 13 (2023) 2735–2747; doi:10.1039/D3CY00347G

data_1568724
_publ_section_title
;
 Rhodium-catalyzed double hydroboration of pyridine: the origin of the
 chemo- and regioselectivities
;
_journal_issue                   9
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              2735
_journal_page_last               2747
_journal_paper_doi               10.1039/D3CY00347G
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C18 H27 B N2 O4 S'
_chemical_formula_sum            'C18 H27 B N2 O4 S'
_chemical_formula_weight         378.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2022-11-06 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.143(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.029(3)
_cell_length_b                   14.490(4)
_cell_length_c                   11.877(3)
_cell_measurement_reflns_used    9637
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.81
_cell_volume                     2061.8(9)
_computing_cell_refinement       'Bruker APEX4'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33518
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.727
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'I\mS 3.0 Microfocus'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       rod
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         3905
_refine_ls_number_restraints     765
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0875
_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^)+(0.1606P)^2^+1.8058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2466
_refine_ls_wR_factor_ref         0.2773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2695
_reflns_number_total             3905
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy00347g2.cif
_cod_data_source_block           A22230O_014
_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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1568723--1568724.cif.
;
_cod_original_cell_volume        2061.7(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1568724
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              74826
_shelx_hkl_checksum              76826