Pd-Catalyzed Dearomative Arylborylation of Indoles
Shen, Chong; Zeidan, Nicolas; Wu, Quan; Breuers, Christian; Liu, Ren-Rong; Jia, Yi-Xia; Lautens, Mark; Chemical Science  (2019) –; doi:10.1039/C8SC05737K

data_1550532
_publ_section_title
;
 Pd-Catalyzed Dearomative Arylborylation of Indoles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05737K
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 B N O3'
_chemical_formula_sum            'C22 H24 B N O3'
_chemical_formula_weight         361.23
_chemical_name_systematic
(10bR,11S)-10b-methyl-11-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10b,11-dihydro-6H-isoindolo[2,1-a]indol-6-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-07-11 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9629(2)
_cell_length_b                   10.4616(2)
_cell_length_c                   18.5419(3)
_cell_measurement_reflns_used    9031
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.54
_cell_measurement_theta_min      4.77
_cell_volume                     1932.33(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            73419
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.563
_diffrn_reflns_theta_max         67.563
_diffrn_reflns_theta_min         2.383
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 2983 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     947
_refine_ls_number_reflns         6794
_refine_ls_number_restraints     2087
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.7031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                6670
_reflns_number_total             6794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05737k2.cif
_cod_data_source_block           d1866a_a
_cod_database_code               1550532
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.898
_shelx_res_checksum              69195