Nickel-catalyzed diastereoselective hydroboration of acrylates with a vinylborane reagent.
Hu, Guanwen; Zhang, Peiqi; Wang, Xinmou; Wan, Chunteng; Fu, Yiyi; Leung, Wa Hung; Lin, Zhenyang; Quan, Yangjian; Chemical science 16 (2025) 13449–13458; doi:10.1039/d5sc02695d

data_1574870
_publ_section_title
;
 Nickel-catalyzed diastereoselective hydroboration of acrylates with a
 vinylborane reagent.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              13449
_journal_page_last               13458
_journal_paper_doi               10.1039/d5sc02695d
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C14 H25 B N2 O2'
_chemical_formula_sum            'C14 H25 B N2 O2'
_chemical_formula_weight         264.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-08-30
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1395(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.70607(10)
_cell_length_b                   14.11052(14)
_cell_length_c                   11.39150(12)
_cell_measurement_reflns_used    6965
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.4800
_cell_measurement_theta_min      4.9840
_cell_volume                     1557.81(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_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    -86.00  -7.00   1.00    2.00    --  -41.13 125.00 -60.00   79
  2  \w    -66.00  30.00   1.00    2.00    --  -41.13  40.00-114.00   96
  3  \w   -114.00 -19.00   1.00    2.00    --  -41.13 -57.00  90.00   95
  4  \w     28.00 107.00   1.00    2.00    --  107.01 -94.00 -30.00   79
  5  \w     80.00 170.00   1.00    2.00    --  107.01  30.00-180.00   90
  6  \w    125.00 178.00   1.00    2.00    --  107.01  77.00   0.00   53
  7  \w    121.00 178.00   1.00    2.00    --  107.01  77.00 120.00   57
  8  \w    109.00 178.00   1.00    2.00    --  107.01 111.00  30.00   69
  9  \w     32.00  58.00   1.00    2.00    --  107.01-111.00 150.00   26
 10  \w     64.00 109.00   1.00    2.00    --  107.01-111.00 150.00   45
 11  \w     32.00 107.00   1.00    2.00    --  107.01 -94.00-180.00   75
 12  \w     37.00 133.00   1.00    2.00    --  107.01 -61.00   0.00   96
 13  \w     80.00 175.00   1.00    2.00    --  107.01  30.00  90.00   95
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0152287000
_diffrn_orient_matrix_UB_12      0.0546014000
_diffrn_orient_matrix_UB_13      0.1171689000
_diffrn_orient_matrix_UB_21      0.1580008000
_diffrn_orient_matrix_UB_22      -0.0113044000
_diffrn_orient_matrix_UB_23      0.0005412000
_diffrn_orient_matrix_UB_31      0.0102885000
_diffrn_orient_matrix_UB_32      0.0937461000
_diffrn_orient_matrix_UB_33      -0.0680052000
_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  0.0151
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9190
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.483
_diffrn_reflns_theta_min         4.994
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0471P)^2^+0.5148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2933
_reflns_number_total             3124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02695d2.cif
_cod_data_source_block           ghuaf1cult_auto
_cod_depositor_comments
'Adding full bibliography for 1574870--1574872.cif.'
_cod_database_code               1574870
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H28 B2 N4'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, 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:
 C11(H11), B1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C21(H21)
2.c X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_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 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.756