Silver-catalyzed synthesis of polyfunctionalized 1,7- and 2,7-benzonaphthyridine scaffolds and access to perlolidine derivatives.
Vashishtha, Kirti; Chahal, Kapil; Bhoi, Namita; Tomy, Donamol; Sridhar, Balasubramanian; Alla, Manjula; Reddy, Kallu Rajender; Organic & biomolecular chemistry 23 (2025) 9677–9682; doi:10.1039/d5ob01410g

data_7160804
_publ_section_title
;
 Silver-catalyzed synthesis of polyfunctionalized 1,7- and
 2,7-benzonaphthyridine scaffolds and access to perlolidine derivatives.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9677
_journal_page_last               9682
_journal_paper_doi               10.1039/d5ob01410g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H20 F N3 O3, 0.855(C H Cl3)'
_chemical_formula_sum            'C26.85 H20.85 Cl2.56 F N3 O3'
_chemical_formula_weight         543.48
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-01-30 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.229(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1446(5)
_cell_length_b                   21.5935(9)
_cell_length_c                   11.7689(5)
_cell_measurement_reflns_used    7861
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.8575
_cell_measurement_theta_min      2.3545
_cell_volume                     2640.0(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_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, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29507
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.355
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             1118
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0692
_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^)+(0.1267P)^2^+1.3375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3374
_reflns_number_total             6046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01410g2.cif
_cod_data_source_block           KB1216_0m
_cod_depositor_comments
'Adding full bibliography for 7160804--7160805.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160804
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.931
_shelx_res_checksum              94020