Synthesis of a fused N-bridged [3.3.1]nonadiquinoline multicyclic skeleton via a metal-free formal [4 + 2] cycloaddition/Mannich/dearomatization domino reaction
Amiri, Kamran; Nayebzadeh, Behrouz; Kamangar, Mohammad; Babazadeh, Mohammad; Ariafard, Alireza; Shiri, Farshad; Rominger, Frank; Balalaie, Saeed; Green Chemistry 25 (2023) 9203–9208; doi:10.1039/D3GC03026A

data_7247831
_publ_section_title
;
 Synthesis of a fused N-bridged [3.3.1]nonadiquinoline multicyclic
 skeleton via a metal-free formal [4 + 2]
 cycloaddition/Mannich/dearomatization domino reaction
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              9203
_journal_page_last               9208
_journal_paper_doi               10.1039/D3GC03026A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C50 H33 N3 O2'
_chemical_formula_weight         707.79
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-16 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   39.4459(15)
_cell_length_b                   39.4459(15)
_cell_length_c                   12.5093(8)
_cell_measurement_reflns_used    4935
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.27
_cell_volume                     16856.5(14)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34031
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.108
_diffrn_reflns_theta_max         24.108
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9576
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             6660
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         5968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0459P)^2^+24.3374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3507
_reflns_number_total             5968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03026a2.cif
_cod_data_source_block           sba191_sq
_cod_original_cell_volume        16856.5(17)
_cod_database_code               7247831
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              78952
_shelx_hkl_checksum              44601
_shelx_fab_checksum              87714