Controlling selectivity in N-heterocycle directed borylation of indoles.
Iqbal, S. A.; Yuan, K.; Cid, J.; Pahl, J.; Ingleson, M. J.; Organic & biomolecular chemistry 19 (2021) 2949–2958; doi:10.1039/d1ob00018g

data_7157932
_publ_section_title
;
 Controlling selectivity in N-heterocycle directed borylation of indoles.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2949
_journal_page_last               2958
_journal_paper_doi               10.1039/d1ob00018g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C13 H9 B Cl2 N2'
_chemical_formula_sum            'C13 H9 B Cl2 N2'
_chemical_formula_weight         274.93
_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'
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_atom_sites_solution_primary     dual
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;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-12-17 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_measurement_temperature    100.0
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_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         2.637
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5813
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'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1302 before and 0.0706 after correction. The Ratio of minimum to maximum transmission is 0.7791. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       rod
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.435
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_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0388P)^2^+0.4860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3128
_reflns_number_total             3636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00018g2.cif
_cod_data_source_block           mo_mi20014_0m
_cod_depositor_comments
'Adding full bibliography for 7157931--7157932.cif.'
_cod_database_code               7157932
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C7(H7), C13(H13), C11(H11), C4(H4), C2(H2), C6(H6), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'