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_7157676
_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_formula_sum            'C34 H24 Br N O4'
_chemical_formula_weight         590.45
_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-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                 91.359(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   13.431(4)
_cell_measurement_reflns_used    5626
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.33
_cell_measurement_theta_min      4.749
_cell_volume                     2665.5(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
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_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 0.982
_diffrn_measured_fraction_theta_max 1.011
_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  0.1610
_diffrn_reflns_av_unetI/netI     0.1005
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 1.011
_diffrn_reflns_limit_h_max       13
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_diffrn_reflns_limit_k_max       20
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_diffrn_reflns_limit_l_max       15
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_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 1.011
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_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.296
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4758
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_exptl_crystal_colour            red
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_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
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_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1810
_refine_ls_R_factor_gt           0.1027
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1568P)^2^+7.4446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2623
_refine_ls_wR_factor_ref         0.3215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2473
_reflns_number_total             4672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01626h2.cif
_cod_data_source_block           d8v19220
_cod_depositor_comments
'Adding full bibliography for 7157675--7157676.cif.'
_cod_original_cell_volume        2665.5(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157676
_shelx_estimated_absorpt_t_min   0.797
_shelx_estimated_absorpt_t_max   0.884
_shelxl_version_number           2013-4
_shelx_res_checksum              83149