Amides as modifiable directing groups in electrophilic borylation.
Iqbal, Saqib A.; Uzelac, Marina; Nawaz, Ismat; Wang, Zhongxing; Jones, T. Harri; Yuan, Kang; Millet, Clement R. P.; Nichol, Gary S.; Chotana, Ghayoor Abbas; Ingleson, Michael J.; Chemical science 14 (2023) 3865–3872; doi:10.1039/d2sc06483a

data_1568667
_publ_section_title
;
 Amides as modifiable directing groups in electrophilic borylation.
;
_journal_issue                   14
_journal_name_full               'Chemical science'
_journal_page_first              3865
_journal_page_last               3872
_journal_paper_doi               10.1039/d2sc06483a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C32 H52 B2 N2 O4'
_chemical_formula_sum            'C32 H52 B2 N2 O4'
_chemical_formula_weight         550.429
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2022-11-03
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-22 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                81.790(3)
_cell_angle_beta                 67.850(4)
_cell_angle_gamma                63.025(4)
_cell_formula_units_Z            1
_cell_length_a                   9.6072(4)
_cell_length_b                   10.0198(4)
_cell_length_c                   10.2726(4)
_cell_measurement_reflns_used    7228
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      29.6120
_cell_measurement_theta_min      4.0790
_cell_volume                     815.76(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9949
_diffrn_measured_fraction_theta_max 0.9382
_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     23.00  87.00   1.00   15.00    --   10.76-157.00 -27.00   64
  2  \w      1.00  62.00   1.00   15.00    --   10.76-119.00 128.00   61
  3  \w    -36.00  61.00   1.00   15.00    --   -9.20  57.00 -30.00   97
  4  \w    -42.00  22.00   1.00   15.00    --   -9.20 -77.00  30.00   64
  5  \w    -79.00  17.00   1.00   15.00    --   -9.20 -57.00-180.00   96
  6  \w    -15.00  51.00   1.00   15.00    --   10.76 -99.00  60.00   66
  7  \w    -82.00  13.00   1.00   15.00    --   -9.20 -38.00 -90.00   95
  8  \w    -82.00  13.00   1.00   15.00    --   -9.20 -38.00   0.00   95
  9  \w    -41.00  21.00   1.00   15.00    --   -9.20  77.00 120.00   62
 10  \w    -15.00  31.00   1.00   15.00    --   -9.20 -99.00  60.00   46
 11  \w    -42.00  42.00   1.00   15.00    --   10.76 -77.00-150.00   84
 12  \w    -42.00 -17.00   1.00   15.00    --   -9.20 -77.00  60.00   25
 13  \w    -15.00  51.00   1.00   15.00    --   10.76 -99.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0333972000
_diffrn_orient_matrix_UB_12      0.0104306000
_diffrn_orient_matrix_UB_13      -0.0730228000
_diffrn_orient_matrix_UB_21      0.0553664000
_diffrn_orient_matrix_UB_22      0.0212292000
_diffrn_orient_matrix_UB_23      0.0120206000
_diffrn_orient_matrix_UB_31      0.0605425000
_diffrn_orient_matrix_UB_32      -0.0758765000
_diffrn_orient_matrix_UB_33      -0.0093463000
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.9949
_diffrn_reflns_Laue_measured_fraction_max 0.9382
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21826
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9382
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.120
_exptl_crystal_description       plate
_exptl_crystal_F_000             300.172
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of dichloromethane and hexane  by solvent layering'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.2391
_refine_diff_density_min         -0.2303
_refine_diff_density_rms         0.0596
_refine_ls_d_res_high            0.7302
_refine_ls_d_res_low             5.3075
_refine_ls_goodness_of_fit_ref   1.0975
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0975
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0104P)^2^+0.0602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0538
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3302
_reflns_number_total             4116
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2sc06483a2.cif
_cod_data_source_block           MI22009
_cod_depositor_comments
'Adding full bibliography for 1568667--1568672.cif.'
_cod_database_code               1568667
_chemical_oxdiff_formula         C32H52B2N2O
_chemical_oxdiff_usercomment     '@ 120 K mji-in-63-r'
_olex2_refinement_description
;
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil.'
_olex2_submission_original_sample_id 'mji-in-63-r '
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.850