Zinc catalysed electrophilic C-H borylation of heteroarenes
Grundy, Matthew; Yuan, Kang; Nichol, Gary Stephen; Ingleson, Michael James; Chemical Science  (2021) –; doi:10.1039/D1SC01883C

data_1562553
_publ_section_title
;
 Zinc catalysed electrophilic C-H borylation of heteroarenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01883C
_journal_year                    2021
_chemical_formula_moiety         'C15 H11 B Br N O2'
_chemical_formula_sum            'C15 H11 B Br N O2'
_chemical_formula_weight         327.97
_chemical_name_systematic
3-(1,3,2-benzodioxaborole)5-bromo-N-methylindole
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-30 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.246(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8776(6)
_cell_length_b                   4.6452(2)
_cell_length_c                   12.9310(6)
_cell_measurement_reflns_used    3593
_cell_measurement_temperature    119.99(11)
_cell_measurement_theta_max      27.5390
_cell_measurement_theta_min      3.9470
_cell_volume                     655.53(6)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.863
_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    -45.00  56.00   1.00   12.50    --  -15.66  20.00 153.00  101
  2  \w    -87.00  13.00   1.00   12.50    --  -15.66 -20.00 -13.00  100
  3  \w    -12.00  89.00   1.00   12.50    --   17.54  20.00 153.00  101
  4  \w    -54.00  10.00   1.00   12.50    --   17.54 -20.00 -13.00   64
  5  \w    -87.00 -40.00   1.00   12.50    --  -15.66-178.00 150.00   47
  6  \w      2.00  79.00   1.00   12.50    --   17.54  57.00-180.00   77
  7  \w     -1.00  39.00   1.00   12.50    --   17.54  77.00  90.00   40
  8  \w     -8.00  29.00   1.00   12.50    --   17.54  77.00-150.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0575972000
_diffrn_orient_matrix_UB_12      -0.0141971000
_diffrn_orient_matrix_UB_13      -0.0040251000
_diffrn_orient_matrix_UB_21      -0.0300183000
_diffrn_orient_matrix_UB_22      -0.0380266000
_diffrn_orient_matrix_UB_23      -0.0575750000
_diffrn_orient_matrix_UB_31      -0.0022089000
_diffrn_orient_matrix_UB_32      0.1471952000
_diffrn_orient_matrix_UB_33      -0.0152644000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7683
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.492
_diffrn_reflns_theta_min         3.429
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97097
_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    1.662
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chlorobenzene'
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0347P)^2^+0.0722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.587
_reflns_number_gt                2480
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01883c2.cif
_cod_data_source_block           mg309_reprocess
_cod_database_code               1562553
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H11 B Br N O2'
_chemical_oxdiff_usercomment     '120 K'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C13(H13), C14(H14), C6(H6), C12(H12), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              90626
_shelx_hkl_checksum              96008
_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 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.924