Diastereoselective amidoboronate formation and transformation from a <i>rac</i> to a different <i>meso</i> amidoboronate <i>via</i> dynamic C-C bonds.
Harders, Patrick; Raeker, Tim; Pietsch, Lorenz; Näther, Christian; Hartke, Bernd; McConnell, Anna J.; Organic & biomolecular chemistry 23 (2025) 10174–10185; doi:10.1039/d5ob01479d

data_7160807
_publ_section_title
;
 Diastereoselective amidoboronate formation and transformation from a
 <i>rac</i> to a different <i>meso</i> amidoboronate <i>via</i> dynamic
 C-C bonds.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10174
_journal_page_last               10185
_journal_paper_doi               10.1039/d5ob01479d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety
'C40 H24 B2 Cl8 F2 N2 O7, 2(C10 H10 Co), 3(C2 H3 N)'
_chemical_formula_sum            'C66 H53 B2 Cl8 Co2 F2 N5 O7'
_chemical_formula_weight         1489.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2025-01-07 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7167(2)
_cell_length_b                   23.6309(2)
_cell_length_c                   30.1749(3)
_cell_measurement_reflns_used    29291
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.1440
_cell_measurement_theta_min      2.8960
_cell_volume                     12633.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_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    -72.00 -44.00   0.50   30.00    --  -41.97 126.00-135.00   56
  2  \w    -93.00 -24.00   0.50   30.00    --  -41.97 -11.00-144.00  138
  3  \w     55.00  88.00   0.50   30.00    --   41.97-126.00 148.00   66
  4  \w     73.00 102.00   0.50   30.00    --   41.97  11.00  28.00   58
  5  \w    -72.00 -47.00   0.50  120.00    --  -96.00 119.00 138.00   50
  6  \w   -134.00 -99.00   0.50  120.00    --  -96.00-119.00  53.00   70
  7  \w   -128.00 -95.00   0.50  120.00    --  -96.00-126.00 148.00   66
  8  \w     72.00  99.00   0.50  120.00    --  117.50-126.00 148.00   54
  9  \w     48.00  73.00   0.50  120.00    --  117.50-119.00  53.00   50
 10  \w    122.00 147.00   0.50  120.00    --  117.50 119.00 138.00   50
 11  \w    111.00 144.00   0.50  120.00    --  117.50 126.00-135.00   66
 12  \w    -35.00  15.00   0.50   30.00    --   41.97 -38.00 120.00  100
 13  \w     44.00  70.00   0.50  120.00    --  117.50 -77.00  30.00   52
 14  \w    104.00 136.00   0.50  120.00    --  117.50  15.00 -30.00   64
 15  \w    104.00 136.00   0.50  120.00    --  117.50  15.00 -90.00   64
 16  \w    103.00 128.00   0.50  120.00    --  117.50  15.00  60.00   50
 17  \w     66.00  92.00   0.50  120.00    --  117.50 -95.00 150.00   52
 18  \w     50.00  93.00   0.50  120.00    --  117.50 -94.00 128.11   86
 19  \w    104.00 135.00   0.50  120.00    --  117.50  15.00-150.00   62
 20  \w    104.00 136.00   0.50  120.00    --  117.50  15.00   0.00   64
 21  \w     48.00  75.00   0.50  120.00    --  117.50 -77.00 -60.00   54
 22  \w    110.00 136.00   0.50  120.00    --  117.50  15.00-180.00   52
 23  \w    109.00 134.00   0.50  120.00    --  117.50  15.00 -60.00   50
 24  \w     58.00  92.00   0.50  120.00    --  117.50 -95.00 120.00   68
 25  \w     53.00  91.00   0.50  120.00    --  117.50 -95.00-180.00   76
 26  \w    105.00 130.00   0.50  120.00    --  117.50  15.00  30.00   50
 27  \w     76.00 101.00   0.50  120.00    --  117.50-125.00-150.00   50
 28  \w     45.00  75.00   0.50  120.00    --  117.50 -77.00-150.00   60
 29  \w     54.00  92.00   0.50  120.00    --  117.50 -95.00  90.00   76
 30  \w    104.00 129.00   0.50  120.00    --  117.50  15.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067727000
_diffrn_orient_matrix_UB_12      0.0067266000
_diffrn_orient_matrix_UB_13      0.0506610000
_diffrn_orient_matrix_UB_21      0.0108452000
_diffrn_orient_matrix_UB_22      -0.0642571000
_diffrn_orient_matrix_UB_23      0.0057283000
_diffrn_orient_matrix_UB_31      0.0859700000
_diffrn_orient_matrix_UB_32      0.0086124000
_diffrn_orient_matrix_UB_33      0.0032583000
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            58806
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.421
_diffrn_reflns_theta_min         2.929
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.774
_exptl_absorpt_correction_T_max  0.49443
_exptl_absorpt_correction_T_min  0.44255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       plate
_exptl_crystal_F_000             6064
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.000121(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     843
_refine_ls_number_reflns         13499
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0914P)^2^+22.8079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1616
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12394
_reflns_number_total             13499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01479d2.cif
_cod_data_source_block           mcconnell39
_cod_depositor_comments
'Adding full bibliography for 7160807--7160809.cif.'
_cod_database_code               7160807
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C66H53B2Cl8Co2F2N5O7
_chemical_oxdiff_usercomment     'Patrick Harders PH74'
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H82A,H82B,H82C} of C82
 At 1.5 times of:
  {H86A,H86B,H86C} of C86, {H84A,H84B,H84C} of C84, {H20A,H20B,H20C} of C20,
  {H34A,H34B,H34C} of C34
2. Restrained distances
 N1-H1
 0.91 with sigma of 0.02
 N2-H2
 0.91 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C13(H13), C21(H21), C41(H41), C42(H42), C43(H43), C45(H45), C71(H71),
 C73(H73), C74(H74), C75(H75)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19),
 C24(H24), C25(H25), C26(H26), C29(H29), C30(H30), C32(H32), C33(H33), C44(H44),
  C51(H51), C52(H52), C53(H53), C54(H54), C55(H55), C61(H61), C62(H62),
 C63(H63), C64(H64), C65(H65), C72(H72)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C34(H34A,H34B,H34C), C82(H82A,H82B,H82C), C84(H84A,H84B,
 H84C), C86(H86A,H86B,H86C)
;
_shelx_res_checksum              41857
_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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.637