Development of a Tunable Chiral Pyridine Ligand Unit for Enantioselective Iridium-Catalyzed C‒H Borylation
Song, Peidong; Hu, Linlin; Yu, Tao; Jiao, Jiao; He, Yangqing; Xu, Liang; Li, Pengfei; ACS Catalysis 11 (2021) 7339–7349; doi:10.1021/acscatal.1c01671

data_4518788
_publ_section_title
;
 Development of a Tunable Chiral Pyridine Ligand Unit for Enantioselective
 Iridium-Catalyzed C--H Borylation
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              7339
_journal_page_last               7349
_journal_paper_doi               10.1021/acscatal.1c01671
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C24 H26 B N O2'
_chemical_formula_sum            'C24 H26 B N O2'
_chemical_formula_weight         371.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-09-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                72.903(4)
_cell_angle_beta                 78.602(4)
_cell_angle_gamma                70.427(4)
_cell_formula_units_Z            2
_cell_length_a                   7.791(2)
_cell_length_b                   10.316(3)
_cell_length_c                   13.717(4)
_cell_measurement_reflns_used    2171
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      2.33
_cell_volume                     986.8(5)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10232
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.293
_diffrn_reflns_theta_min         1.563
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0651 before and 0.0491 after correction.
The Ratio of minimum to maximum transmission is 0.8861.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0695
_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^)+(0.0500P)^2^+1.5568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1753
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2632
_reflns_number_total             3934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01671_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4518787--4518790.cif.'
_cod_database_code               4518788
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C10 \\sim C00J: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.01 within 2A
3.a Ternary CH refined with riding coordinates:
 C008(H008)
3.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00M(H00M),
 C00N(H00N)
3.c Idealised Me refined as rotating group:
 C00O(H00a,H00k,H00l), C00P(H00o,H00p,H00q), C00Q(H00r,H00s,H00t), C00R(H00u,
 H00v,H00w)
;
_shelx_res_checksum              25137
_shelx_hkl_checksum              85926
_olex2_submission_special_instructions 'No special instructions were received'