Design of a modular, palladium-catalyzed carbonylative synthesis of pyrido[2,1-α]isoindoles <i>via</i> benzyne 1,3-dipolar cycloaddition.
Wong, Karina S.; Ghanbari, Mohammad; Arndtsen, Bruce A.; Chemical communications (Cambridge, England) 61 (2025) 4192–4195; doi:10.1039/d4cc06483f

data_7134262
_publ_section_title
;
 Design of a modular, palladium-catalyzed carbonylative synthesis of
 pyrido[2,1-&#x3b1;]isoindoles <i>via</i> benzyne 1,3-dipolar
 cycloaddition.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4192
_journal_page_last               4195
_journal_paper_doi               10.1039/d4cc06483f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32
_chemical_name_systematic
6-(4-methoxypgenyl)pyridoxine[2,1-alpha]isoindole
_chemical_properties_physical    Air-sensitive,Oxygen-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2024-09-23 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4292(4)
_cell_length_b                   7.6601(2)
_cell_length_c                   22.9023(6)
_cell_measurement_reflns_used    1912
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.456
_cell_measurement_theta_min      3.860
_cell_volume                     2882.24(13)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'Bruker APEX3'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            41004
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.456
_diffrn_reflns_theta_min         3.860
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.7314
_exptl_absorpt_correction_T_min  0.5741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0730P)^2^+0.8646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1912
_reflns_number_total             2849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06483f2.cif
_cod_data_source_block           KW1
_cod_depositor_comments          'Adding full bibliography for 7134262.cif.'
_cod_database_code               7134262
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.900
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              26576
_shelx_hkl_checksum              29746