Selective Synthesis of 3-(9 H-Carbazol-2-yl)indolin-2-ones and Spiro[tetrahydrocarbazole-3,3'-oxindoles] via a HOTf Catalyzed Three-Component Reaction.
Yang, Ren-Yin; Sun, Jing; Sun, Qiu; Yan, Chao-Guo; The Journal of organic chemistry 83 (2018) 5909–5919; doi:10.1021/acs.joc.8b00196

data_4035785
_publ_section_title
;
 Selective Synthesis of 3-(9 H-Carbazol-2-yl)indolin-2-ones and
 Spiro[tetrahydrocarbazole-3,3'-oxindoles] via a HOTf Catalyzed
 Three-Component Reaction.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5909
_journal_page_last               5919
_journal_paper_doi               10.1021/acs.joc.8b00196
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C33 H28 N2 O2, C2 H6 O'
_chemical_formula_sum            'C35 H34 N2 O3'
_chemical_formula_weight         530.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.042(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4054(10)
_cell_length_b                   21.7037(15)
_cell_length_c                   9.9449(7)
_cell_measurement_reflns_used    6246
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.32
_cell_measurement_theta_min      2.27
_cell_volume                     2871.6(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29285
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         2.422
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0686P)^2^+0.5154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3410
_reflns_number_total             6576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00196_si_002.cif
_cod_data_source_block           6b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035785
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              66747
_shelx_hkl_checksum              63837