Organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization: sustainable access to indole-2,3-fused diazocanes
Wang, Lin-Xuan; Qiu, Bin; An, Xiao-De; Dong, Pei-Zhen; Liu, Rui-Bin; Xiao, Jian; Green Chemistry 23 (2021) 8181–8186; doi:10.1039/D1GC02570H

data_7243651
_publ_section_title
;
 Organocatalytic cascade aldimine condensation/[1,6]-hydride
 transfer/Mannich-type cyclization: sustainable access to indole-2,3-fused
 diazocanes
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8181
_journal_page_last               8186
_journal_paper_doi               10.1039/D1GC02570H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C21 H23 N3'
_chemical_formula_weight         317.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-16 deposited with the CCDC.	2021-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.081(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4459(6)
_cell_length_b                   7.45856(17)
_cell_length_c                   16.2431(6)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9460
_cell_measurement_theta_min      3.0880
_cell_volume                     1650.99(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5325
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.215
_diffrn_reflns_theta_max         67.215
_diffrn_reflns_theta_min         3.258
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0038(5)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0611P)^2^+0.5453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2546
_reflns_number_total             2962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02570h2.cif
_cod_data_source_block           exp_11691
_cod_depositor_comments          'Adding full bibliography for 7243651.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7243651
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.938
_shelx_res_checksum              26617