Cobalt-catalyzed double hydroboration of pyridines
Höeg, Finn; Luxenberger, Lea; Fedulin, Andrey; Jacobi von Wangelin, Axel; Chemical Science 15 (2024) 5201–5210; doi:10.1039/D3SC05418G

data_1571195
_publ_section_title
;
 Cobalt-catalyzed double hydroboration of pyridines
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              5201
_journal_page_last               5210
_journal_paper_doi               10.1039/D3SC05418G
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C38 H63 B Co2 N O3 P'
_chemical_formula_sum            'C38 H63 B Co2 N O3 P'
_chemical_formula_weight         741.53
_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_creation_date             2023-07-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-10 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.883(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4812(5)
_cell_length_b                   8.4448(2)
_cell_length_c                   28.0381(8)
_cell_measurement_reflns_used    57064
_cell_measurement_temperature    99.92(18)
_cell_measurement_theta_max      29.2640
_cell_measurement_theta_min      2.5010
_cell_volume                     3788.36(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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      99.92(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4127
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_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    -82.00  18.00   1.00   85.00    --   -9.92 -57.00  90.00  100
  2  \w    -42.00  43.00   1.00   85.00    --   10.70 -77.00 -60.00   85
  3  \w    -14.00  85.00   1.00   85.00    --   10.70  38.00 -90.00   99
  4  \w    -17.00  84.00   1.00   85.00    --   10.70  57.00  90.00  101
  5  \w    -27.00  91.00   1.00   85.00    --   10.70  19.00  30.00  118
  6  \w      2.00  64.00   1.00   85.00    --   10.70-120.00-149.09   62
  7  \w      8.00  69.00   1.00   85.00    --   10.70-128.00  90.86   61
  8  \w    -85.00 -42.00   1.00   85.00    --   -9.92 153.00 -53.80   43
  9  \w    -69.00 -30.00   1.00   85.00    --   -9.92 129.00  50.29   39
 10  \w    -15.00  31.00   1.00   85.00    --   -9.92 -99.00-150.00   46
 11  \w    -43.00  21.00   1.00   85.00    --   -9.92  77.00-120.00   64
 12  \w    -85.00 -42.00   1.00   85.00    --   -9.92 153.00-142.19   43
 13  \w    -85.00 -42.00   1.00   85.00    --   -9.92 153.00 175.73   43
 14  \w    -43.00  21.00   1.00   85.00    --   -9.92  77.00  90.00   64
 15  \w    -43.00  21.00   1.00   85.00    --   -9.92  77.00   0.00   64
 16  \w    -86.00 -43.00   1.00   85.00    --   -9.92 154.00  55.37   43
 17  \w     22.00  88.00   1.00   85.00    --   10.70-156.00  14.31   66
 18  \w      2.00  64.00   1.00   85.00    --   10.70-120.00-126.51   62
;
_diffrn_measurement_device       'four-circle 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      -0.0030134000
_diffrn_orient_matrix_UB_12      -0.0561286000
_diffrn_orient_matrix_UB_13      0.0183126000
_diffrn_orient_matrix_UB_21      0.0403906000
_diffrn_orient_matrix_UB_22      -0.0288595000
_diffrn_orient_matrix_UB_23      -0.0000304000
_diffrn_orient_matrix_UB_31      0.0180102000
_diffrn_orient_matrix_UB_32      0.0554212000
_diffrn_orient_matrix_UB_33      0.0185367000
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            127400
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.620
_diffrn_reflns_theta_min         2.525
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.893
_refine_diff_density_min         -1.367
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         10251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+8.2090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8971
_reflns_number_total             10251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05418g2.cif
_cod_data_source_block           FH34_auto
_cod_depositor_comments
'Adding full bibliography for 1571191--1571195.cif.'
_cod_database_code               1571195
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C28H46BCoNO3P
_chemical_oxdiff_usercomment     'Hoeeg/JvW, 20.02.2023, Mo, 100K'
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
1.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C18(H18A,H18B,
 H18C), C28(H28A,H28B,H28C), C14(H14A,H14B,H14C), C34(H34A,H34B,H34C), C38(H38A,
 H38B,H38C), C25(H25A,H25B,H25C), C36(H36A,H36B,H36C), C27(H27A,H27B,H27C),
 C26(H26A,H26B,H26C), C35(H35A,H35B,H35C), C4(H4A,H4B,H4C), C37(H37A,H37B,H37C),
  C6(H6A,H6B,H6C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              87563
_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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.854