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_1568025
_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         'C52 H43 N5 O4, C7 H8'
_chemical_formula_sum            'C59 H51 N5 O4'
_chemical_formula_weight         894.05
_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
_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                90
_cell_angle_beta                 95.275(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.815(2)
_cell_length_b                   24.526(3)
_cell_length_c                   8.429(2)
_cell_measurement_reflns_used    41238
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.869
_cell_measurement_theta_min      0.818
_cell_volume                     4490.7(13)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'costum designed PXII GUI'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.778
_diffrn_measurement_device_type
;
Eiger2 X 16M, High Precision 1-Axis Goniostat with Staeubli sample changing
robot
;
_diffrn_measurement_method       '180\deg \p scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.61992
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.778
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            79085
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.778
_diffrn_reflns_theta_full        21.836
_diffrn_reflns_theta_max         27.869
_diffrn_reflns_theta_min         0.818
_diffrn_source                   'P11@PETRA III, DESY, Hamburg, Germany'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         12553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0891P)^2^+1.3580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10297
_reflns_number_total             12553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05409d2.cif
_cod_data_source_block           TXQ178-1TolHex_a
_cod_depositor_comments
'Adding full bibliography for 1568025--1568030.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1568025
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              10994
_shelx_hkl_checksum              3877