Nitrogen-doped polycyclic aromatic hydrocarbons by a one-pot Suzuki coupling/intramolecular S<sub>N</sub>Ar reaction.
Tian, Xiaoqi; Shoyama, Kazutaka; Würthner, Frank; Chemical science 14 (2023) 284–290; doi:10.1039/d2sc05409d

data_1568028
_publ_section_title
;
 Nitrogen-doped polycyclic aromatic hydrocarbons by a one-pot Suzuki
 coupling/intramolecular S<sub>N</sub>Ar reaction.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              284
_journal_page_last               290
_journal_paper_doi               10.1039/d2sc05409d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C53 H44 N4 O4, C7 H8'
_chemical_formula_sum            'C60 H52 N4 O4'
_chemical_formula_weight         893.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-12 deposited with the CCDC.	2022-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                104.872(6)
_cell_angle_beta                 90.047(5)
_cell_angle_gamma                109.465(6)
_cell_formula_units_Z            4
_cell_length_a                   16.7768(15)
_cell_length_b                   17.5515(16)
_cell_length_c                   17.6585(16)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.02
_cell_measurement_theta_min      2.78
_cell_volume                     4717.0(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16662
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.813
_diffrn_reflns_theta_min         2.601
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1247
_refine_ls_number_reflns         16662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.2027
_refine_ls_R_factor_gt           0.1799
_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^)+(0.2186P)^2^+51.6700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4843
_refine_ls_wR_factor_ref         0.4979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12270
_reflns_number_total             16662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05409d2.cif
_cod_data_source_block           970_txq01_125_a_tw
_cod_depositor_comments
'Adding full bibliography for 1568025--1568030.cif.'
_cod_database_code               1568028
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              88943
_shelx_hkl_checksum              37446