The Acylative Kinetic Resolution of 1,2-Azaborine Naphthols
Prindl, Martha I.; McKay, Aidan P.; Cordes, David Bradford; Smith, Andrew D.; Chemical Science  (2026) –; doi:10.1039/D6SC02046A

data_1577063
_publ_section_title
;
 The Acylative Kinetic Resolution of 1,2-Azaborine Naphthols
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D6SC02046A
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H22 B N O'
_chemical_formula_sum            'C26 H22 B N O'
_chemical_formula_weight         375.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2026-03-02
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-03-09 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.099(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6777(2)
_cell_length_b                   11.3747(2)
_cell_length_c                   10.3590(3)
_cell_measurement_reflns_used    12968
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      73.1310
_cell_measurement_theta_min      4.4580
_cell_volume                     971.91(4)
_computing_cell_refinement       'CrysAlisPro 1.171.44.121a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 44.121a 64-bit (release 04-09-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.121a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_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     24.00 110.00   0.50    0.20    --   94.65-127.00-131.00  172
  2  \w      1.00 102.00   0.50    0.05    --   50.17-127.00-131.00  202
  3  \w      1.00 102.00   0.50    0.05    --   50.17-127.00-131.00  202
  4  \w     30.00  98.00   0.50    0.20    --   94.65 -95.00-120.00  136
  5  \w     13.00 113.00   0.50    0.05    --   50.17-145.00  60.00  200
  6  \w     25.00 121.00   0.50    0.20    --   94.65-145.00  60.00  192
  7  \w     29.00  59.00   0.50    0.20    --   94.65 -95.00  90.00   60
  8  \w     76.00 102.00   0.50    0.20    --   94.65 -95.00  90.00   52
  9  \w     76.00 102.00   0.50    0.20    --   94.65 -95.00  30.00   52
 10  \w     22.00  51.00   0.50    0.20    --   94.65 -45.00  90.00   58
 11  \w     14.00  40.00   0.50    0.05    --   42.00  83.00 169.59   52
 12  \w     10.00  38.00   0.50    0.05    --   38.00  84.00  71.38   56
 13  \w    -40.00   5.00   0.50    0.05    --    6.00 118.00  12.48   90
 14  \w    -30.00   2.00   0.50    0.05    --   18.00 122.00-102.54   64
 15  \w     20.00  52.00   0.50    0.05    --   46.00  79.00-106.75   64
 16  \w     24.00  52.00   0.50    0.05    --   50.00  79.00 -89.10   56
 17  \w     21.00  52.00   0.50    0.05    --   46.00  76.00 -61.33   62
 18  \w     25.00  52.00   0.50    0.05    --   50.00  76.00-161.77   54
 19  \w     25.00  52.00   0.50    0.05    --   50.00  77.00 -21.24   54
 20  \w     24.00  52.00   0.50    0.05    --   50.00  78.00  35.21   56
 21  \w     25.00  52.00   0.50    0.05    --   50.00  76.00  92.16   54
 22  \w     24.00  52.00   0.50    0.05    --   50.00  79.00 142.55   56
 23  \w     44.00 132.00   0.50    0.05    --   62.00  68.00 146.80  176
 24  \w     75.00 101.00   0.50    0.20    --   94.65  77.00  30.00   52
 25  \w    118.00 144.00   0.50    0.20    --   94.65  77.00  30.00   52
 26  \w     79.00 145.00   0.50    0.20    --   94.65  77.00   0.00  132
 27  \w     75.00 107.00   0.50    0.20    --   94.65  77.00 -60.00   64
 28  \w     40.00 128.00   0.50    0.05    --   58.00  69.00-129.65  176
 29  \w     77.00 166.00   0.50    0.20    --   94.65 127.00 -55.00  178
 30  \w     65.00 120.00   0.50    0.05    --   50.17 145.00 112.00  110
 31  \w     65.00 164.00   0.50    0.20    --   94.65 145.00 112.00  198
 32  \w    -51.00 -22.00   0.50    0.20    --  -91.62  45.00 120.00   58
 33  \w   -104.00 -25.00   0.50    0.20    --  -91.62  77.00 150.00  158
 34  \w    -69.00 -22.00   0.50    0.20    --  -91.62  61.00 -60.00   94
 35  \w   -104.00 -30.00   0.50    0.20    --  -99.00 114.00  -0.71  148
 36  \w   -106.00 -21.00   0.50    0.20    --  -91.62 125.00 -90.00  170
 37  \w   -109.00 -21.00   0.50    0.20    --  -91.62 127.00 -55.00  176
 38  \w   -102.00  -1.00   0.50    0.05    --  -51.05 127.00 -55.00  202
 39  \w   -121.00 -22.00   0.50    0.20    --  -91.62 145.00 112.00  198
 40  \w   -114.00 -13.00   0.50    0.05    --  -51.05 145.00 112.00  202
 41  \w    -48.00   4.00   0.50    0.05    --   -2.00 119.00 164.43  104
 42  \w   -102.00 -76.00   0.50    0.20    --  -86.00 -59.00  21.57   52
 43  \w   -104.00 -76.00   0.50    0.20    --  -91.62 -77.00  60.00   56
 44  \w   -152.00 -75.00   0.50    0.20    --  -91.62 -77.00   0.00  154
 45  \w   -105.00 -77.00   0.50    0.20    --  -91.62 -77.00 -30.00   56
 46  \w   -115.00 -80.00   0.50    0.20    --  -99.00 -73.00 -11.65   70
 47  \w   -162.00 -75.00   0.50    0.20    --  -99.00 -75.00-166.24  174
 48  \w   -166.00 -80.00   0.50    0.20    --  -99.00 -76.00-121.52  172
 49  \w   -138.00 -78.00   0.50    0.20    --  -99.00 -74.00-109.07  120
 50  \w   -145.00-112.00   0.50    0.20    --  -99.00 -72.00 -83.73   66
 51  \w   -107.00 -76.00   0.50    0.20    --  -99.00 -72.00 -83.73   62
 52  \w   -164.00-139.00   0.50    0.20    --  -99.00 -73.00 -11.65   50
 53  \w   -114.00 -75.00   0.50    0.20    --  -99.00 -73.00 170.37   78
 54  \w   -163.00 -77.00   0.50    0.20    --  -99.00 -73.00 158.17  172
 55  \w   -144.00 -73.00   0.50    0.20    --  -94.00 -71.00 129.43  142
 56  \w   -161.00 -76.00   0.50    0.20    --  -99.00 -72.00 111.07  170
 57  \w    -81.00 -55.00   0.50    0.05    --  -74.00 -69.00 138.49   52
 58  \w    -87.00 -57.00   0.50    0.05    --  -74.00 -69.00 167.55   60
 59  \w    -80.00 -54.00   0.50    0.05    --  -70.00 -68.00 108.72   52
 60  \w   -133.00-108.00   0.50    0.05    --  -70.00 -69.00 -49.54   50
 61  \w    -77.00 -51.00   0.50    0.05    --  -70.00 -69.00 -49.54   52
 62  \w    -90.00 -64.00   0.50    0.20    --  -82.00 -68.00 -76.11   52
 63  \w   -104.00 -78.00   0.50    0.20    --  -99.00 -71.00-156.03   52
 64  \w    -84.00 -58.00   0.50    0.05    --  -74.00 -67.00-177.08   52
 65  \w    -86.00 -60.00   0.50    0.05    --  -74.00 -68.00-122.08   52
 66  \w   -126.00 -73.00   0.50    0.20    --  -90.00 -69.00 -71.56  106
 67  \w    -93.00 -67.00   0.50    0.20    --  -82.00 -66.00   3.91   52
 68  \w    -94.00 -69.00   0.50    0.20    --  -86.00 -67.00  57.31   50
 69  \w    -89.00 -63.00   0.50    0.20    --  -78.00 -67.00  51.58   52
 70  \w    -94.00 -68.00   0.50    0.20    --  -86.00 -68.00 106.13   52
 71  \w   -136.00 -50.00   0.50    0.05    --  -66.00 -66.00  16.73  172
 72  \w   -154.00-127.00   0.50    0.20    --  -86.00 -67.00  57.31   54
 73  \w    -99.00 -62.00   0.50    0.20    --  -78.00 -66.00  -6.30   74
 74  \w    -93.00 -62.00   0.50    0.20    --  -78.00 -66.00 -59.64   62
 75  \w    -89.00 -63.00   0.50    0.20    --  -78.00 -65.00 -26.35   52
 76  \w   -164.00 -84.00   0.50    0.20    --  -99.00 -65.00 -33.02  160
 77  \w   -143.00-112.00   0.50    0.20    --  -86.00 -65.00-113.78   62
 78  \w   -116.00 -62.00   0.50    0.20    --  -78.00 -66.00-167.58  108
 79  \w    -80.00 -55.00   0.50    0.05    --  -70.00 -65.00-161.93   50
 80  \w   -102.00 -73.00   0.50    0.20    --  -86.00 -65.00-113.78   58
 81  \w    -98.00 -69.00   0.50    0.20    --  -82.00 -63.00-103.32   58
 82  \w    -91.00 -56.00   0.50    0.05    --  -70.00 -64.00-112.60   70
 83  \w    -91.00 -65.00   0.50    0.20    --  -78.00 -63.00-146.32   52
 84  \w   -137.00 -52.00   0.50    0.05    --  -66.00 -64.00 -98.48  170
 85  \w   -149.00-123.00   0.50    0.20    --  -82.00 -63.00-103.32   52
 86  \w   -143.00-117.00   0.50    0.20    --  -78.00 -63.00 -50.49   52
 87  \w   -133.00 -50.00   0.50    0.05    --  -62.00 -62.00 -79.90  166
 88  \w    -90.00 -65.00   0.50    0.20    --  -78.00 -63.00 -50.49   50
 89  \w   -133.00 -50.00   0.50    0.05    --  -62.00 -62.00 -79.90  166
 90  \w   -137.00 -54.00   0.50    0.05    --  -66.00 -62.00  -2.37  166
 91  \w    -83.00 -56.00   0.50    0.05    --  -66.00 -62.00  55.00   54
 92  \w    -81.00 -56.00   0.50    0.05    --  -70.00 -64.00  70.19   50
 93  \w   -100.00 -69.00   0.50    0.20    --  -82.00 -63.00  78.98   62
 94  \w   -106.00 -77.00   0.50    0.20    --  -86.00 -61.00  70.61   58
 95  \w   -157.00-112.00   0.50    0.20    --  -86.00 -61.00  70.61   90
 96  \w   -140.00 -68.00   0.50    0.20    --  -78.00 -62.00 149.24  144
 97  \w   -121.00 -65.00   0.50    0.05    --  -51.05-145.00  60.00  112
 98  \w   -161.00 -65.00   0.50    0.20    --  -91.62-145.00  60.00  192
 99  \w   -162.00 -77.00   0.50    0.20    --  -91.62-127.00-131.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1812862000
_diffrn_orient_matrix_UB_12      -0.0080498000
_diffrn_orient_matrix_UB_13      -0.0124499000
_diffrn_orient_matrix_UB_21      0.0078846000
_diffrn_orient_matrix_UB_22      -0.1349852000
_diffrn_orient_matrix_UB_23      -0.0090580000
_diffrn_orient_matrix_UB_31      0.0442480000
_diffrn_orient_matrix_UB_32      -0.0084036000
_diffrn_orient_matrix_UB_33      0.1556376000
_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  0.0469
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            34520
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.537
_diffrn_reflns_theta_min         4.491
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.121a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       rod
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1654 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0480P)^2^+0.0827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                3684
_reflns_number_total             3812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc02046a2.cif
_cod_data_source_block           15
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1577063
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.857
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O19-H19
 0.98 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              91310