Ligand-controlled regiodivergent Ni-catalyzed <i>trans</i>-hydroboration/carboboration of internal alkynes with B<sub>2</sub>pin<sub>2</sub>.
Chen, Zunsheng; Nie, Biao; Li, Xiaoning; Liu, Teng; Li, Chunsheng; Huang, Jiuzhong; Chemical science 15 (2024) 2236–2242; doi:10.1039/d3sc04184k

data_1570695
_publ_section_title
;
 Ligand-controlled regiodivergent Ni-catalyzed
 <i>trans</i>-hydroboration/carboboration of internal alkynes with
 B<sub>2</sub>pin<sub>2</sub>.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2236
_journal_page_last               2242
_journal_paper_doi               10.1039/d3sc04184k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C20 H28 B N O2'
_chemical_formula_sum            'C20 H28 B N O2'
_chemical_formula_weight         325.24
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g18rk
_audit_creation_date             2022-10-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-25 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.376(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9832(5)
_cell_length_b                   9.6904(4)
_cell_length_c                   13.4858(4)
_cell_measurement_reflns_used    5145
_cell_measurement_temperature    166(20)
_cell_measurement_theta_max      71.2190
_cell_measurement_theta_min      5.4340
_cell_volume                     1926.03(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      166(20)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     80.00 115.00   0.50    0.50    --   42.30  77.00  60.00   70
  2  \w    104.00 129.00   0.50    0.50    --   42.30  77.00 -60.00   50
  3  \w    -13.00  13.00   0.50    0.50    --   42.30 -82.00 -90.00   52
  4  \w     34.00  84.00   0.50    0.50    --   42.30  57.00-180.00  100
  5  \w     88.00 120.00   0.50    0.50    --   42.30  77.00 -30.00   64
  6  \w     92.00 132.00   0.50    0.50    --   42.30  77.00-180.00   80
  7  \w     83.00 119.00   0.50    0.50    --   42.30  77.00 120.00   72
  8  \w     44.00  86.00   0.50    0.50    --   42.30 -82.00 -90.00   84
  9  \w     81.00 127.00   0.50    0.50    --   42.30  77.00  30.00   92
 10  \w     88.00 191.00   0.50    1.00    --  101.60  82.00-120.00  206
 11  \w     46.00 131.00   0.50    1.00    --  101.60 -50.00 120.00  170
 12  \w     87.00 144.00   0.50    1.00    --  101.60  82.00   0.00  114
 13  \w     82.00 154.00   0.50    1.00    --  101.60  64.00 -30.00  144
 14  \w    134.00 169.00   0.50    1.00    --  101.60  82.00 -30.00   70
 15  \w     70.00 146.00   0.50    1.00    --  101.60  50.00 -30.00  152
 16  \w     70.00 189.00   0.50    1.00    --  101.60  50.00 -60.00  238
 17  \w     64.00 145.00   0.50    1.00    --  101.60 -82.00-120.00  162
 18  \w      3.00  29.00   0.50    0.50    --   42.10 -77.00  60.00   52
 19  \w    105.00 132.00   0.50    0.50    --   42.10  77.00   0.00   54
 20  \w     74.00 124.00   0.50    1.00    --  101.60  50.00-180.00  100
 21  \w    166.00 191.00   0.50    1.00    --  101.60  82.00 120.00   50
 22  \w    143.00 184.00   0.50    1.00    --  101.60  82.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0249845000
_diffrn_orient_matrix_UB_12      0.1210167000
_diffrn_orient_matrix_UB_13      0.0738408000
_diffrn_orient_matrix_UB_21      0.0883873000
_diffrn_orient_matrix_UB_22      0.0222855000
_diffrn_orient_matrix_UB_23      -0.0409945000
_diffrn_orient_matrix_UB_31      -0.0498668000
_diffrn_orient_matrix_UB_32      0.1005774000
_diffrn_orient_matrix_UB_33      -0.0798346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10323
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.355
_diffrn_reflns_theta_min         2.998
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0802P)^2^+1.2441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3160
_reflns_number_total             3658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04184k2.cif
_cod_data_source_block           2822
_cod_depositor_comments
'Adding full bibliography for 1570693--1570697.cif.'
_cod_database_code               1570695
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.927
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              16833
_shelx_hkl_checksum              91242
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.281