Versatile method for the synthesis of aminobenziodoxolones and its application to one-pot coupling of arylboronic acids with simple amines.
Kawanaka, Kazuki; Narita, Shusuke; Kiyokawa, Kensuke; Minakata, Satoshi; Chemical science 16 (2025) 19389–19396; doi:10.1039/d5sc06301a

data_1575818
_publ_section_title
;
 Versatile method for the synthesis of aminobenziodoxolones and its
 application to one-pot coupling of arylboronic acids with simple amines.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              19389
_journal_page_last               19396
_journal_paper_doi               10.1039/d5sc06301a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C16 H23 N O2'
_chemical_formula_sum            'C16 H23 N O2'
_chemical_formula_weight         261.35
_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             2025-07-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-07-10 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.78020(10)
_cell_length_b                   9.48310(10)
_cell_length_c                   22.5161(3)
_cell_measurement_reflns_used    10907
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      76.4120
_cell_measurement_theta_min      3.9360
_cell_volume                     1447.60(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.133a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.133a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.133a (Rigaku OD, 2024)'
_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_temperature      123.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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    -78.00 -36.00   0.50    0.74    -- -106.55  57.00 120.00   84
  2  \w    -62.00 -34.00   0.50    0.74    -- -106.55  77.00 -30.00   56
  3  \w    -86.00 -34.00   0.50    0.74    -- -106.55  57.00 -60.00  104
  4  \w   -127.00 -86.00   0.50    0.74    -- -106.55  77.00 -30.00   82
  5  \w    -87.00 -62.00   0.50    0.74    -- -106.55  57.00   0.00   50
  6  \w    -76.00 -37.00   0.50    0.74    -- -106.55  48.00 -12.00   78
  7  \w    -86.00 -40.00   0.50    0.74    -- -106.55  57.00-120.00   92
  8  \w    -87.00 -62.00   0.50    0.74    -- -106.55  57.00-150.00   50
  9  \w    -61.00 -35.00   0.50    0.74    -- -106.55  37.00-150.00   52
 10  \w    -63.00 -34.00   0.50    0.74    -- -106.55  37.00-180.00   58
 11  \w    -50.00 -11.00   0.50    0.19    --  -47.51  48.00 -12.00   78
 12  \w    -64.00 -39.00   0.50    0.74    -- -106.55  37.00 120.00   50
 13  \w    -62.00 -37.00   0.50    0.74    -- -106.55  37.00 150.00   50
 14  \w     69.00 120.00   0.50    0.19    --   47.51  57.00  90.00  102
 15  \w     76.00 109.00   0.50    0.19    --   47.51  48.00 -12.00   66
 16  \w     46.00  73.00   0.50    0.19    --   47.51  48.00 -12.00   54
 17  \w     33.00  66.00   0.50    0.19    --   47.51  57.00  90.00   66
 18  \w     94.00 120.00   0.50    0.74    --   86.25  77.00  30.00   52
 19  \w    117.00 142.00   0.50    0.74    --   86.25  77.00  90.00   50
 20  \w     84.00 152.00   0.50    0.74    --   86.25  57.00 120.00  136
 21  \w     64.00  90.00   0.50    0.74    --   86.25  77.00  90.00   52
 22  \w     65.00 104.00   0.50    0.74    --   86.25  77.00  60.00   78
 23  \w     86.00 137.00   0.50    0.74    --   86.25  19.00  90.00  102
 24  \w     65.00  92.00   0.50    0.74    --   86.25  77.00  30.00   54
 25  \w     90.00 115.00   0.50    0.74    --   86.25  48.00 -12.00   50
 26  \w     75.00 117.00   0.50    0.74    --   86.25  37.00-180.00   84
 27  \w     14.00  44.00   0.50    0.74    --   86.25 -57.00  30.00   60
 28  \w     18.00  44.00   0.50    0.74    --   86.25 -57.00  60.00   52
 29  \w     15.00  42.00   0.50    0.74    --   86.25 -57.00 120.00   54
 30  \w    -25.00   4.00   0.50    0.19    --   47.51 -19.00  90.00   58
 31  \w    -26.00   4.00   0.50    0.19    --   47.51 -19.00  60.00   60
 32  \w    -23.00   2.00   0.50    0.19    --   47.51 -19.00 -90.00   50
 33  \w    -22.00   3.00   0.50    0.19    --   47.51 -19.00-150.00   50
 34  \w    -24.00  33.00   0.50    0.19    --   47.51 -48.00-159.00  114
 35  \w   -113.00 -88.00   0.50    0.74    -- -106.55 -77.00 120.00   50
 36  \w   -164.00 -88.00   0.50    0.74    -- -106.55 -67.00 118.81  152
 37  \w   -174.00-148.00   0.50    0.74    -- -106.55 -19.00 120.00   52
 38  \w   -147.00 -99.00   0.50    0.74    -- -106.55 -19.00 120.00   96
 39  \w   -166.00 -90.00   0.50    0.74    -- -106.55 -72.00  79.25  152
 40  \w   -152.00-100.00   0.50    0.74    -- -106.55 -19.00  30.00  104
 41  \w   -177.00-107.00   0.50    0.74    -- -106.55 -48.00-159.00  140
 42  \w   -118.00 -34.00   0.50    0.19    --  -47.51 -48.00-159.00  168
 43  \w   -110.00 -79.00   0.50    0.74    -- -106.55 125.00-150.00   62
 44  \w   -105.00 -55.00   0.50    0.74    -- -106.55 125.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2269840000
_diffrn_orient_matrix_UB_12      0.0064998000
_diffrn_orient_matrix_UB_13      -0.0011659000
_diffrn_orient_matrix_UB_21      0.0108577000
_diffrn_orient_matrix_UB_22      -0.0969764000
_diffrn_orient_matrix_UB_23      0.0548360000
_diffrn_orient_matrix_UB_31      0.0034049000
_diffrn_orient_matrix_UB_32      -0.1302019000
_diffrn_orient_matrix_UB_33      -0.0408759000
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.643
_diffrn_reflns_theta_min         3.927
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.133a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_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     174
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0610P)^2^+0.2925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2678
_reflns_number_total             2983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06301a2.cif
_cod_data_source_block           20250701_kk_auto
_cod_depositor_comments          'Adding full bibliography for 1575818.cif.'
_cod_database_code               1575818
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C16 H23 N1 O2'
_chemical_oxdiff_usercomment     KK_321
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.895
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C5(H5A,H5B), C6(H6A,H6B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C14(H14), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              83032
_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 2.303
_oxdiff_exptl_absorpt_empirical_full_min 0.642