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_7160808
_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         'C19 H12 B Cl F N O2'
_chemical_formula_sum            'C19 H12 B Cl F N O2'
_chemical_formula_weight         351.56
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2025-01-08 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.8175(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.93061(14)
_cell_length_b                   15.29640(15)
_cell_length_c                   10.61622(12)
_cell_measurement_reflns_used    12807
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9840
_cell_measurement_theta_min      4.5340
_cell_volume                     1584.11(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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 2014/4 (Sheldrick, 2014)'
_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 1.000
_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    -67.00   0.00   0.50    0.60    --  -42.22 105.00-100.00  134
  2  \w    -67.00   0.00   0.50    0.60    --  -42.22 105.00-100.00  134
  3  \w     22.00  79.00   0.50    0.60    --   42.22-105.00 159.00  114
  4  \w   -158.00-102.00   0.50    2.40    --  -96.00-105.00 159.00  112
  5  \w     44.00  92.00   0.50    2.40    --  117.50-105.00 159.00   96
  6  \w     27.00  59.00   0.50    0.60    --   42.22  58.00 153.48   64
  7  \w    -35.00  19.00   0.50    0.60    --   42.22 -38.00 150.00  108
  8  \w     26.00  54.00   0.50    0.60    --   42.22  61.00   1.85   56
  9  \w     26.00  54.00   0.50    0.60    --   42.22  61.00  30.60   56
 10  \w     27.00  59.00   0.50    0.60    --   42.22  58.00  96.69   64
 11  \w    -35.00  19.00   0.50    0.60    --   42.22 -38.00  90.00  108
 12  \w     34.00  88.00   0.50    0.60    --   42.22-125.00 -90.00  108
 13  \w     26.00  54.00   0.50    0.60    --   42.22  61.00  51.07   56
 14  \w     26.00  54.00   0.50    0.60    --   42.22  61.00 -86.99   56
 15  \w   -136.00 -81.00   0.50    2.40    --  -96.00 -15.00 150.00  110
 16  \w   -136.00 -81.00   0.50    2.40    --  -96.00 -15.00-120.00  110
 17  \w   -136.00 -81.00   0.50    2.40    --  -96.00 -15.00-150.00  110
 18  \w    103.00 136.00   0.50    2.40    --  117.50  15.00-180.00   66
 19  \w    103.00 136.00   0.50    2.40    --  117.50  15.00 -60.00   66
 20  \w     44.00  75.00   0.50    2.40    --  117.50 -77.00 150.00   62
 21  \w     44.00  75.00   0.50    2.40    --  117.50 -77.00 -90.00   62
 22  \w     44.00  75.00   0.50    2.40    --  117.50 -77.00 -30.00   62
 23  \w    105.00 178.00   0.50    2.40    --  117.50  45.00-180.00  146
 24  \w     44.00  75.00   0.50    2.40    --  117.50 -77.00-120.00   62
 25  \w     44.00  75.00   0.50    2.40    --  117.50 -77.00-180.00   62
 26  \w     46.00 101.00   0.50    2.40    --  117.50-125.00-120.00  110
 27  \w    104.00 166.00   0.50    2.40    --  117.50  30.00   0.00  124
 28  \w     44.00  75.00   0.50    2.40    --  117.50 -77.00   0.00   62
 29  \w    124.00 178.00   0.50    2.40    --  117.50  77.00-120.00  108
 30  \w     46.00 101.00   0.50    2.40    --  117.50-125.00 -60.00  110
 31  \w    103.00 136.00   0.50    2.40    --  117.50  15.00  90.00   66
 32  \w    112.00 178.00   0.50    2.40    --  117.50 125.00 -30.00  132
 33  \w     44.00  93.00   0.50    2.40    --  117.50 -97.00-129.75   98
 34  \w     46.00 101.00   0.50    2.40    --  117.50-125.00 -90.00  110
 35  \w     44.00  92.00   0.50    2.40    --  117.50 -95.00-180.00   96
 36  \w    103.00 136.00   0.50    2.40    --  117.50  15.00 -30.00   66
 37  \w    103.00 136.00   0.50    2.40    --  117.50  15.00 120.00   66
 38  \w    123.00 178.00   0.50    2.40    --  117.50 105.00-100.00  110
 39  \w    -19.00  35.00   0.50    0.60    --  -42.22  38.00-120.00  108
 40  \w     27.00  59.00   0.50    0.60    --   42.22  58.00-173.74   64
 41  \w     26.00  54.00   0.50    0.60    --   42.22  61.00 121.45   56
 42  \w      1.00  65.00   0.50    0.60    --   42.22 -77.00   0.00  128
 43  \w     27.00  57.00   0.50    0.60    --   42.22  60.00 -46.11   60
 44  \w     28.00  60.00   0.50    0.60    --   42.22  56.00-110.93   64
 45  \w     27.00  57.00   0.50    0.60    --   42.22  60.00-136.92   60
;
_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      -0.0429700000
_diffrn_orient_matrix_UB_12      0.0847938000
_diffrn_orient_matrix_UB_13      0.0476346000
_diffrn_orient_matrix_UB_21      0.1254004000
_diffrn_orient_matrix_UB_22      0.0473102000
_diffrn_orient_matrix_UB_23      0.0022638000
_diffrn_orient_matrix_UB_31      -0.0858763000
_diffrn_orient_matrix_UB_32      0.0267229000
_diffrn_orient_matrix_UB_33      -0.1554392000
_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  0.0198
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16948
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.294
_diffrn_reflns_theta_min         4.533
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0419P)^2^+0.5648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3285
_reflns_number_total             3397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01479d2.cif
_cod_data_source_block           mcconnell41
_cod_depositor_comments
'Adding full bibliography for 7160807--7160809.cif.'
_cod_database_code               7160808
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C19H12BClFNO2
_chemical_oxdiff_usercomment     'Patrick Harders PH-66'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19)
;
_shelx_res_checksum              95757
_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 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.832