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_1568026
_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           1
_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
;
2022-07-15 deposited with the CCDC.	2022-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                95.160(2)
_cell_angle_beta                 99.293(2)
_cell_angle_gamma                115.715(2)
_cell_formula_units_Z            1
_cell_length_a                   8.3457(3)
_cell_length_b                   9.3455(3)
_cell_length_c                   17.6411(6)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.45
_cell_measurement_theta_min      2.58
_cell_volume                     1203.41(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 0.999
_diffrn_measured_fraction_theta_max 0.966
_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_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21931
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.575
_diffrn_reflns_theta_min         2.580
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 2723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         8928
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0684
_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^)+(0.1144P)^2^+0.0821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1819
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.728
_reflns_number_gt                7659
_reflns_number_total             8928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05409d2.cif
_cod_data_source_block           972_TXQ01_126_k2_0m_a
_cod_depositor_comments
'Adding full bibliography for 1568025--1568030.cif.'
_cod_original_cell_volume        1203.41(7)
_cod_database_code               1568026
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              25998
_shelx_hkl_checksum              43812