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_1571194
_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         'C24 H38 Co N O P'
_chemical_formula_sum            'C24 H38 Co N O P'
_chemical_formula_weight         446.45
_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     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                 95.001(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.3080(5)
_cell_length_b                   9.2019(2)
_cell_length_c                   22.7534(5)
_cell_measurement_reflns_used    34520
_cell_measurement_temperature    99.94(17)
_cell_measurement_theta_max      73.0740
_cell_measurement_theta_min      2.8980
_cell_volume                     4652.95(18)
_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      99.94(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4127
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -117.00 -18.00   1.00   27.50    --  -42.33 -38.00 -90.00   99
  2  \w   -117.00 -18.00   1.00   27.50    --  -42.33 -38.00  90.00   99
  3  \w   -114.00 -14.00   1.00   27.50    --  -42.33 -57.00-150.00  100
  4  \w    -22.00  32.00   1.00   27.50    --  -42.33  38.00 -90.00   54
  5  \w   -114.00 -14.00   1.00   27.50    --  -42.33 -57.00 -90.00  100
  6  \w    -22.00  32.00   1.00   27.50    --  -42.33  38.00  90.00   54
  7  \w   -114.00 -14.00   1.00   27.50    --  -42.33 -57.00   0.00  100
  8  \w    -87.00  -6.00   1.00   27.50    --  -42.33 125.00 120.00   81
  9  \w   -114.00 -14.00   1.00   27.50    --  -42.33 -57.00  60.00  100
 10  \w    -44.00  31.00   1.00   27.50    --  -42.33  57.00   0.00   75
 11  \w   -114.00 -14.00   1.00   27.50    --  -42.33 -57.00 150.00  100
 12  \w      9.00  42.00   1.00   27.50    --   42.33  80.00 -76.66   33
 13  \w      9.00  42.00   1.00   27.50    --   42.33  80.00  64.03   33
 14  \w      9.00  42.00   1.00   27.50    --   42.33  79.00-165.81   33
 15  \w     10.00  42.00   1.00   27.50    --   42.33  78.00  11.76   32
 16  \w     27.00  98.00   1.00   27.50    --   42.33-125.00  30.00   71
 17  \w      9.00  42.00   1.00   27.50    --   42.33  79.00 147.39   33
 18  \w     26.00 108.00   1.00  110.00    --  104.98-104.00 -42.06   82
 19  \w     76.00 177.00   1.00  110.00    --  104.98  60.00 139.19  101
 20  \w     77.00 177.00   1.00  110.00    --  104.98  56.00 -69.77  100
 21  \w     76.00 177.00   1.00  110.00    --  104.98  61.00 -60.00  101
 22  \w     28.00 109.00   1.00  110.00    --  104.98-110.00  64.85   81
 23  \w     32.00 112.00   1.00  110.00    --  104.98-125.00 150.00   80
 24  \w     76.00 177.00   1.00  110.00    --  104.98  61.00-180.00  101
 25  \w     76.00 177.00   1.00  110.00    --  104.98  61.00 120.00  101
 26  \w     32.00  72.00   1.00  110.00    --  104.98 -45.00  30.00   40
 27  \w     76.00 177.00   1.00  110.00    --  104.98  61.00 150.00  101
 28  \w     75.00 178.00   1.00  110.00    --  104.98  64.00-145.50  103
 29  \w     77.00 177.00   1.00  110.00    --  104.98  57.00  55.47  100
 30  \w     79.00 106.00   1.00  110.00    --  104.98  45.00-180.00   27
 31  \w     32.00 112.00   1.00  110.00    --  104.98-125.00 -60.00   80
 32  \w     75.00 142.00   1.00  110.00    --  104.98  68.00-172.59   67
 33  \w     76.00 105.00   1.00  110.00    --  104.98  61.00  60.00   29
 34  \w     76.00 108.00   1.00  110.00    --  104.98  61.00-150.00   32
 35  \w     76.00 122.00   1.00  110.00    --  104.98  61.00   0.00   46
 36  \w     33.00  93.00   1.00  110.00    --  104.98 -61.00 150.00   60
 37  \w     74.00 100.00   1.00  110.00    --  104.98  70.00-119.90   26
 38  \w    108.00 140.00   1.00  110.00    --  104.98  61.00  60.00   32
 39  \w     77.00 176.00   1.00  110.00    --  104.98  58.00-121.16   99
 40  \w     80.00 178.00   1.00  110.00    --  104.98  45.00 -30.00   98
 41  \w     76.00 102.00   1.00  110.00    --  104.98  61.00  30.00   26
 42  \w     79.00 106.00   1.00  110.00    --  104.98  45.00 120.00   27
 43  \w     23.00 107.00   1.00  110.00    --  104.98 -94.00 150.00   84
 44  \w     77.00 103.00   1.00  110.00    --  104.98  56.00 -10.20   26
 45  \w     79.00 178.00   1.00  110.00    --  104.98  45.00  90.00   99
 46  \w     33.00  93.00   1.00  110.00    --  104.98 -61.00 -60.00   60
 47  \w     76.00 102.00   1.00  110.00    --  104.98  61.00 -30.00   26
 48  \w     74.00 178.00   1.00  110.00    --  104.98  70.00   1.97  104
 49  \w     75.00 105.00   1.00  110.00    --  104.98  64.00 -96.15   30
 50  \w     74.00 100.00   1.00  110.00    --  104.98  69.00  77.80   26
;
_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      0.0211879000
_diffrn_orient_matrix_UB_12      0.0236829000
_diffrn_orient_matrix_UB_13      -0.0619425000
_diffrn_orient_matrix_UB_21      0.0198772000
_diffrn_orient_matrix_UB_22      -0.1600503000
_diffrn_orient_matrix_UB_23      -0.0017919000
_diffrn_orient_matrix_UB_31      -0.0629529000
_diffrn_orient_matrix_UB_32      -0.0426300000
_diffrn_orient_matrix_UB_33      -0.0279878000
_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  0.1098
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            92564
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.853
_diffrn_reflns_theta_min         2.660
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58866
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       plate
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         9286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0943P)^2^+2.9998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7934
_reflns_number_total             9286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05418g2.cif
_cod_data_source_block           FH39_auto
_cod_depositor_comments
'Adding full bibliography for 1571191--1571195.cif.'
_cod_database_code               1571194
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C24H38CoNOP
_chemical_oxdiff_usercomment     'Hoeg/JvW, 26.01.2023, Cu, 100K'
_shelx_estimated_absorpt_t_max   0.881
_shelx_estimated_absorpt_t_min   0.292
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C6(H6A,H6B)
1.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C28(H28), C2(H2), C4(H4), C3(H3)
1.c Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C21(H21A,H21B,H21C), C44(H44A,H44B,H44C), C48(H48A,H48B,
 H48C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C), C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C37(H37A,H37B,H37C),
 C38(H38A,H38B,H38C), C32(H32A,H32B,H32C), C8(H8A,H8B,H8C), C34(H34A,H34B,H34C),
  C14(H14A,H14B,H14C), C33(H33A,H33B,H33C), C13(H13A,H13B,H13C), C9(H9A,H9B,
 H9C), C36(H36A,H36B,H36C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              4329
_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 1.992
_oxdiff_exptl_absorpt_empirical_full_min 0.600