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_7244749
_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_absolute_configuration rm
_chemical_formula_sum            'C27 H25 N O3'
_chemical_formula_weight         411.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.355(2)
_cell_length_b                   6.4076(7)
_cell_length_c                   13.2555(16)
_cell_measurement_reflns_used    1302
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.4350
_cell_measurement_theta_min      3.6170
_cell_volume                     2068.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12326
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.229
_diffrn_reflns_theta_max         67.229
_diffrn_reflns_theta_min         3.630
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       0.0088(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0842
_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^)+(0.1042P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.2664
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                1495
_reflns_number_total             3375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00387b2.cif
_cod_data_source_block           exp_11683
_cod_depositor_comments
'Adding full bibliography for 7244749--7244751.cif.'
_cod_database_code               7244749
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.929
_shelx_res_checksum              7775