Nickel-Catalyzed Decarboxylative Cross-Coupling of Indole-3-acetic Acids with Aryl Bromides by Convergent Paired Electrolysis
Wang, Zhen-Hua; Wei, Lei; Jiao, Ke-Jin; Ma, Cong; Mei, Tian-Sheng; Chemical Communications  (2022) –; doi:10.1039/D2CC02641D

data_7130280
_publ_section_title
;
 Nickel-Catalyzed Decarboxylative Cross-Coupling of Indole-3-acetic Acids
 with Aryl Bromides by Convergent Paired Electrolysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02641D
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_sum            'C19 H16 N2 O'
_chemical_formula_weight         288.34
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.115(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   25.192(2)
_cell_length_b                   5.6061(5)
_cell_length_c                   33.579(3)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.344
_cell_measurement_theta_min      4.853
_cell_volume                     4453.1(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0491
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            75235
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.830
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 5002 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.6(8)
_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     1195
_refine_ls_number_reflns         17400
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.7154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                13297
_reflns_number_total             17400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02641d2.cif
_cod_data_source_block           mo_d8v211027_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130280
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
_shelx_res_checksum              47326