Nano Au/Pd-catalysed ‘on-water’ synthesis of C3‒C3′ diaryl-oxindole scaffolds via N2-selective dearomatization of indole
Gohain, Shivanee Borpatra; Basumatary, Monika; Boruah, Purna K.; Das, Manash R.; Thakur, Ashim Jyoti; Green Chemistry 22 (2020) 170–179; doi:10.1039/C9GC02370D

data_7235256
_publ_section_title
;
 Nano Au/Pd-catalysed &#x2018;on-water&#x2019; synthesis of C3--C3&#x2032;
 diaryl-oxindole scaffolds via N2-selective dearomatization of indole
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              170
_journal_page_last               179
_journal_paper_doi               10.1039/C9GC02370D
_journal_volume                  22
_journal_year                    2020
_chemical_formula_sum            'C96 H56 Br12 N12 O5'
_chemical_formula_weight         2416.44
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-04 deposited with the CCDC.	2019-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   8.6559(5)
_cell_length_b                   15.6308(9)
_cell_length_c                   16.2787(8)
_cell_measurement_reflns_used    4236
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.42
_cell_measurement_theta_min      2.50
_cell_volume                     2202.5(2)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_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  0.2068
_diffrn_reflns_av_unetI/netI     0.1478
_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       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50377
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.482
_diffrn_reflns_theta_min         2.502
_exptl_absorpt_coefficient_mu    5.518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.210
_exptl_transmission_factor_max   0.315
_exptl_transmission_factor_min   0.185
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(12)
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1928
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0593P)^2^+1.0931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2350
_reflns_number_total             5555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02370d2.cif
_cod_data_source_block           aa
_cod_depositor_comments
;Adding full bibliography for 7235256.cif.

 Adding full bibliography for 7235256.cif.
;
_cod_database_code               7235256
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.271
_shelx_estimated_absorpt_t_max   0.390
_shelx_res_checksum              4435