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_7157931
_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_absolute_configuration ad
_chemical_formula_moiety         'C15 H9 B Cl2 N2 O'
_chemical_formula_sum            'C15 H9 B Cl2 N2 O'
_chemical_formula_weight         314.95
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-16
_audit_creation_method
;
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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2660(2)
_cell_length_b                   11.4559(3)
_cell_length_c                   12.8747(4)
_cell_measurement_reflns_used    5822
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.4590
_cell_measurement_theta_min      5.1140
_cell_volume                     1366.65(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -82.00  15.00   1.00   15.00    --  -38.34 100.00 173.00   97
  2  \w      6.00  83.00   1.00   15.00    --   38.34-100.00  67.00   77
  3  \w    104.00 178.00   1.00   30.00    --  116.00 100.00 173.00   74
  4  \w     31.00 107.00   1.00   30.00    --  116.00-100.00  67.00   76
  5  \w   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00 -60.00  110
  6  \w    -40.00  71.00   1.00   15.00    --   38.34 -57.00-180.00  111
  7  \w    -21.00  74.00   1.00   15.00    --   38.34 -77.00 -90.00   95
  8  \w     38.00 149.00   1.00   30.00    --  116.00 -61.00  60.00  111
  9  \w     29.00 107.00   1.00   30.00    --  116.00 -94.00  90.00   78
 10  \w     61.00 146.00   1.00   30.00    --  116.00 178.00  90.00   85
 11  \w     35.00 109.00   1.00   30.00    --  116.00-111.00 -60.00   74
 12  \w    103.00 178.00   1.00   30.00    --  116.00  77.00 -30.00   75
 13  \w     29.00 107.00   1.00   30.00    --  116.00 -94.00 -60.00   78
 14  \w     83.00 178.00   1.00   30.00    --  116.00  61.00  30.00   95
 15  \w     38.00 149.00   1.00   30.00    --  116.00 -61.00-150.00  111
 16  \w     35.00 178.00   1.00   30.00    --  116.00  15.00   0.00  143
 17  \w   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00  60.00  110
 18  \w   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00-180.00  110
 19  \w   -116.00  -6.00   1.00   15.00    --  -38.34 -57.00 120.00  110
 20  \w   -118.00  -7.00   1.00   15.00    --  -38.34 -38.00 -30.00  111
 21  \w   -126.00 -37.00   1.00   15.00    --  -38.34 178.00-120.00   89
 22  \w    -70.00  41.00   1.00   15.00    --  -38.34  38.00  90.00  111
 23  \w     78.00 152.00   1.00   30.00    --  116.00  30.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1450553000
_diffrn_orient_matrix_UB_12      0.0132912000
_diffrn_orient_matrix_UB_13      0.0572648000
_diffrn_orient_matrix_UB_21      -0.0806688000
_diffrn_orient_matrix_UB_22      -0.0404600000
_diffrn_orient_matrix_UB_23      -0.0982300000
_diffrn_orient_matrix_UB_31      0.0106872000
_diffrn_orient_matrix_UB_32      -0.1275420000
_diffrn_orient_matrix_UB_33      0.0371739000
_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  0.0707
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.297
_diffrn_reflns_theta_min         5.168
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.252
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.531
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0938P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2541
_reflns_number_total             2851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00018g2.cif
_cod_data_source_block           mi20009_refinalized
_cod_depositor_comments
'Adding full bibliography for 7157931--7157932.cif.'
_cod_database_code               7157931
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C15 H9 B1 Cl2 N2 O1'
_chemical_oxdiff_usercomment     '@ 120 K SI-222'
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.287
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C4(H4), C14(H14), C5(H5), C2(H2), C11(H11), C13(H13), C12(H12)
;
_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 1.571
_oxdiff_exptl_absorpt_empirical_full_min 0.682