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_1571191
_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         'C22 H34 Co N O P'
_chemical_formula_sum            'C22 H34 Co N O P'
_chemical_formula_weight         418.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-28
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-10 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7865(5)
_cell_length_b                   10.4516(3)
_cell_length_c                   13.5026(3)
_cell_measurement_reflns_used    37080
_cell_measurement_temperature    99.96(18)
_cell_measurement_theta_max      29.2710
_cell_measurement_theta_min      3.8120
_cell_volume                     2086.73(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2063
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.925
_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    -15.00  31.00   1.00   45.00    --   -9.87 -99.00  90.00   46
  2  \w    -69.00  26.00   1.00   45.00    --   10.57 -19.00 120.00   95
  3  \w    -78.00  99.00   1.00   45.00    --   10.57   0.00-120.00  177
  4  \w    -18.00  83.00   1.00   45.00    --   10.57  57.00  60.00  101
  5  \w    -18.00  83.00   1.00   45.00    --   10.57  57.00 -60.00  101
  6  \w    -42.00  43.00   1.00   45.00    --   10.57 -77.00  60.00   85
  7  \w     -5.00  60.00   1.00   45.00    --   12.00-112.00-133.21   65
  8  \w      2.00  66.00   1.00   45.00    --   12.00-121.00 146.10   64
  9  \w      7.00  69.00   1.00   45.00    --   12.00-126.00 -10.67   62
 10  \w    -15.00  31.00   1.00   45.00    --   -9.87 -99.00 120.00   46
 11  \w    -73.00 -34.00   1.00   45.00    --   -9.87 137.00-178.19   39
 12  \w    -67.00 -28.00   1.00   45.00    --   -9.87 126.00 -35.32   39
 13  \w    -68.00 -30.00   1.00   45.00    --   -9.87 128.00  -2.16   38
 14  \w    -86.00 -43.00   1.00   45.00    --   -9.87 154.00 148.56   43
 15  \w     16.00  81.00   1.00   45.00    --   10.57-147.00  42.22   65
 16  \w      2.00  65.00   1.00   45.00    --   12.00-120.00-161.10   63
 17  \w    -86.00 -43.00   1.00   45.00    --   -9.87 154.00 -61.14   43
 18  \w    -15.00  31.00   1.00   45.00    --   -9.87 -99.00  60.00   46
 19  \w     -4.00  59.00   1.00   45.00    --   10.57-113.00  16.00   63
 20  \w    -78.00  99.00   1.00   45.00    --   10.57   0.00-150.00  177
 21  \w    -78.00  27.00   1.00   45.00    --   10.57   0.00-120.00  105
 22  \w    -78.00  99.00   1.00   45.00    --   10.57   0.00-180.00  177
;
_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      0.0219563000
_diffrn_orient_matrix_UB_12      0.0596828000
_diffrn_orient_matrix_UB_13      -0.0067499000
_diffrn_orient_matrix_UB_21      0.0416590000
_diffrn_orient_matrix_UB_22      -0.0321547000
_diffrn_orient_matrix_UB_23      -0.0076945000
_diffrn_orient_matrix_UB_31      -0.0090198000
_diffrn_orient_matrix_UB_32      -0.0030059000
_diffrn_orient_matrix_UB_33      -0.0515543000
_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  0.0572
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            89288
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         3.141
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         2.261
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Flack x determined using 2208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5397
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0156P)^2^+9.7245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                5022
_reflns_number_total             5397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05418g2.cif
_cod_data_source_block           FAI-FH-02
_cod_depositor_comments
'Adding full bibliography for 1571191--1571195.cif.'
_cod_database_code               1571191
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C110 H170 N5 O5 P5 Co5 '
_chemical_oxdiff_usercomment     'Fedulin/JvW, 02.12.2021, Mo, 100K'
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C11(H11A,H11B,
 H11C), C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,
 H22B,H22C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              11752
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.783