Synthesis of indoline-fused eight-membered azaheterocycles through Zn-catalyzed dearomatization of indoles and subsequent base-promoted C-C activation.
Mu, Yuanyang; Yuan, Yang; Wang, Ye; Xu, Murong; Feng, Ye; Zhao, Yulei; Li, Yanzhong; Organic & biomolecular chemistry 18 (2020) 6916–6926; doi:10.1039/d0ob01626h

data_7157675
_publ_section_title
;
 Synthesis of indoline-fused eight-membered azaheterocycles through
 Zn-catalyzed dearomatization of indoles and subsequent base-promoted C-C
 activation.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6916
_journal_page_last               6926
_journal_paper_doi               10.1039/d0ob01626h
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_sum            'C34 H25 N O4'
_chemical_formula_weight         511.55
_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-2013
_audit_update_record
;
2020-05-29 deposited with the CCDC.	2020-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2273(3)
_cell_length_b                   12.6042(5)
_cell_length_c                   29.1348(12)
_cell_measurement_reflns_used    5819
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.629
_cell_measurement_theta_min      5.295
_cell_volume                     2654.02(19)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13426
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         2.648
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
; 
 Flack x determined using 1516 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.1596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4249
_reflns_number_total             5164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01626h2.cif
_cod_data_source_block           mo_d8v19221_0m
_cod_depositor_comments
'Adding full bibliography for 7157675--7157676.cif.'
_cod_database_code               7157675
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4
_shelx_res_checksum              27295