Cascade dearomative [4 + 2] cycloaddition of indoles with in situ generated ortho-quinone methides: practical access to divergent indoline-fused polycycles
Dong, Pei-Zhen; Qiu, Bin; An, Xiao-De; Xiao, Jian; Green Chemistry 24 (2022) 3772–3777; doi:10.1039/D2GC00387B

data_7244751
_publ_section_title
;
 Cascade dearomative [4 + 2] cycloaddition of indoles with in situ
 generated ortho-quinone methides: practical access to divergent
 indoline-fused polycycles
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3772
_journal_page_last               3777
_journal_paper_doi               10.1039/D2GC00387B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C23 H17 N O3'
_chemical_formula_weight         355.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-12 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.010(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9483(6)
_cell_length_b                   17.9325(13)
_cell_length_c                   16.0130(11)
_cell_measurement_reflns_used    1598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1420
_cell_measurement_theta_min      4.4140
_cell_volume                     3431.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.222
_diffrn_reflns_theta_max         67.222
_diffrn_reflns_theta_min         4.447
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0951
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2612
_refine_ls_wR_factor_ref         0.3137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1702
_reflns_number_total             3056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00387b2.cif
_cod_data_source_block           10439
_cod_depositor_comments
'Adding full bibliography for 7244749--7244751.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244751
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.923
_shelx_res_checksum              62428