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_1570697
_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         'C22 H24 B N O2'
_chemical_formula_sum            'C22 H24 B N O2'
_chemical_formula_weight         345.23
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2hmdtc
_audit_creation_date             2023-12-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                102.169(11)
_cell_angle_beta                 105.217(10)
_cell_angle_gamma                103.684(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6547(10)
_cell_length_b                   10.2621(13)
_cell_length_c                   10.6861(15)
_cell_measurement_reflns_used    3179
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7220
_cell_measurement_theta_min      2.2730
_cell_volume                     949.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -16.00  71.00   1.00    1.50    --   11.90  57.00 -30.00   87
  2  \w     48.00  78.00   1.00    1.50    --   11.90 178.00 -60.00   30
  3  \w    -36.00  61.00   1.00    1.50    --  -11.27  57.00-180.00   97
  4  \w    -77.00  13.00   1.00    1.50    --  -11.27 -57.00  30.00   90
  5  \w    -82.00 -57.00   1.00    1.50    --  -11.27 -38.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0032808000
_diffrn_orient_matrix_UB_12      -0.0026766000
_diffrn_orient_matrix_UB_13      -0.0659968000
_diffrn_orient_matrix_UB_21      0.0758989000
_diffrn_orient_matrix_UB_22      0.0442712000
_diffrn_orient_matrix_UB_23      0.0284629000
_diffrn_orient_matrix_UB_31      0.0252838000
_diffrn_orient_matrix_UB_32      -0.0596813000
_diffrn_orient_matrix_UB_33      -0.0020003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7165
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.064
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0472P)^2^+0.3589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2706
_reflns_number_total             3351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04184k2.cif
_cod_data_source_block           385-8_2
_cod_depositor_comments
'Adding full bibliography for 1570693--1570697.cif.'
_cod_database_code               1570697
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.988
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              14231
_shelx_hkl_checksum              56691
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.603