Asymmetric catalytic concise synthesis of 3-(3-indolomethyl)-oxindoles for the construction of trigolute analogs.
Yang, Zun; Jiang, Zheng; Tan, Zheng; Yu, Han; Feng, Xiaoming; Liu, Xiaohua; Chemical communications (Cambridge, England) 60 (2024) 10926–10929; doi:10.1039/d4cc03327b

data_7133678
_publ_section_title
;
 Asymmetric catalytic concise synthesis of 3-(3-indolomethyl)-oxindoles
 for the construction of trigolute analogs.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10926
_journal_page_last               10929
_journal_paper_doi               10.1039/d4cc03327b
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H24 N2 O6, C H Cl3'
_chemical_formula_sum            'C30 H25 Cl3 N2 O6'
_chemical_formula_weight         615.87
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-02-08 deposited with the CCDC.	2024-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4395(2)
_cell_length_b                   17.2117(4)
_cell_length_c                   18.1895(4)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.54
_cell_volume                     2955.25(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18447
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.535
_exptl_absorpt_coefficient_mu    3.195
_exptl_absorpt_correction_T_max  0.9444
_exptl_absorpt_correction_T_min  0.4746
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       rod
_exptl_crystal_F_000             1272
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 2166 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.039(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5364
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0554P)^2^+0.5502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5204
_reflns_number_total             5364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03327b2.cif
_cod_data_source_block           zhp035
_cod_depositor_comments          'Adding full bibliography for 7133678.cif.'
_cod_database_code               7133678
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.260
_shelx_estimated_absorpt_t_max   0.576
_shelx_res_checksum              3997
_shelx_hkl_checksum              57453