2-Pyridone-assisted palladium-catalyzed regioselective arylation of naphthamides
Prajapati, Jayprakash; Chatterjee, Sourav; RSC Advances 16 (2026) 12180–12185; doi:10.1039/D6RA00358C

data_7251685
_publ_section_title
;
 2-Pyridone-assisted palladium-catalyzed regioselective arylation of
 naphthamides
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              12180
_journal_page_last               12185
_journal_paper_doi               10.1039/D6RA00358C
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety         'C31 H19 Br F6 N2 O2, [+ solvents]'
_chemical_formula_sum            'C31 H19 Br F6 N2 O2'
_chemical_formula_weight         645.39
_chemical_name_systematic        SNM_MKK_C2_125_B1
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_audit_update_record
;
2025-07-25 deposited with the CCDC.	2026-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.923(2)
_cell_length_b                   17.004(2)
_cell_length_c                   19.383(2)
_cell_measurement_reflns_used    9718
_cell_measurement_temperature    118.00
_cell_measurement_theta_max      23.369
_cell_measurement_theta_min      2.421
_cell_volume                     5577.6(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      118.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker apex photon IV'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            163058
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.344
_diffrn_reflns_theta_min         1.997
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5670
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1014 before and 0.0761 after correction.
The Ratio of minimum to maximum transmission is 0.7606.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.012
_refine_diff_density_max         1.652
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0039(6)
_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   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         6260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0770
_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^)+(0.1247P)^2^+8.5869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4328
_reflns_number_total             6260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ra00358c2.cif
_cod_data_source_block           mo_snm_mkk_c2_125_b_1
_cod_original_cell_volume        5577.8(12)
_cod_database_code               7251685
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C18) = Uanis(F6)
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C16(H16), C12(H12), C4(H4), C23(H23), C14(H14), C28(H28), C27(H27),
 C10(H10), C24(H24), C9(H9), C31(H31), C30(H30), C5(H5), C7(H7), C6(H6)
;
_shelx_res_checksum              2992
_olex2_exptl_crystal_mounting_method 'Nylone Loop'
_olex2_submission_original_sample_id SNM_MKK_C2_125_B1
_olex2_submission_special_instructions 'No special instructions were received'