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_1568672
_publ_section_title
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 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_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 B2 Br2 N O, C6 H6'
_chemical_formula_sum            'C30 H31 B2 Br2 N O'
_chemical_formula_weight         603.00
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-22
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.83580(10)
_cell_length_b                   11.60820(10)
_cell_length_c                   22.5888(2)
_cell_measurement_reflns_used    21042
_cell_measurement_temperature    119.99(17)
_cell_measurement_theta_max      29.4350
_cell_measurement_theta_min      3.6110
_cell_volume                     2579.10(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 16.1042
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.945
_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    -59.00  15.00   1.00    5.00    --  -15.82 106.00  22.00   74
  2  \w    -15.00  60.00   1.00    5.00    --   17.54-106.00 -76.00   75
  3  \w    -88.00 -39.00   1.00    5.00    --  -15.82-178.00  90.00   49
  4  \w    -39.00  11.00   1.00    5.00    --  -15.82 -77.00   0.00   50
  5  \w    -33.00  51.00   1.00    5.00    --  -15.82  57.00 -30.00   84
  6  \w    -35.00  53.00   1.00    5.00    --  -15.82  38.00  90.00   88
  7  \w    -39.00  11.00   1.00    5.00    --  -15.82 -77.00 120.00   50
  8  \w     -9.00  39.00   1.00    5.00    --   17.54  77.00 120.00   48
  9  \w     39.00  90.00   1.00    5.00    --   17.54 178.00-120.00   51
 10  \w    -54.00  47.00   1.00    5.00    --   17.54 -19.00 150.00  101
 11  \w     -1.00  87.00   1.00    5.00    --   17.54  38.00   0.00   88
 12  \w    -83.00   1.00   1.00    5.00    --  -15.82 -57.00  60.00   84
 13  \w     -9.00  39.00   1.00    5.00    --   17.54  77.00 -60.00   48
 14  \w      1.00  48.00   1.00    5.00    --   17.54  57.00-150.00   47
 15  \w     -9.00  39.00   1.00    5.00    --   17.54  77.00-120.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            57746
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.495
_diffrn_reflns_theta_min         3.510
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_recrystallization_method
'Crystallised at room temperature by layering concentrated DCM solution with benzene.'
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.261
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.494(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0253P)^2^+1.8106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0578
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                6143
_reflns_number_total             6623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06483a2.cif
_cod_data_source_block           mu667b_reprocess
_cod_depositor_comments
'Adding full bibliography for 1568667--1568672.cif.'
_cod_database_code               1568672
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.506(9)
 0.494(9)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C20(H20A,H20B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C16(H16), C12(H12), C6(H6), C11(H11), C13(H13), C5(H5),
 C30(H30), C28(H28), C25(H25), C29(H29), C27(H27), C26(H26)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              51417
_shelx_hkl_checksum              22638
_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
;