Palladium(II)/Lewis acid catalyzed oxidative olefination of 2-benzamidopyridine 1-oxide with acrylates: synthesis of isoindolinones.
Patel, Dharmik M.; Patel, Raj N.; Rathod, Nileshkumar B.; Patel, Sachinkumar D.; Thakur, Dinesh G.; Sonawane, Mahesh A.; Ghosh, Subhash Chandra; Organic & biomolecular chemistry 23 (2025) 2697–2703; doi:10.1039/d5ob00021a

data_7160372
_publ_section_title
;
 Palladium(II)/Lewis acid catalyzed oxidative olefination of
 2-benzamidopyridine 1-oxide with acrylates: synthesis of isoindolinones.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2697
_journal_page_last               2703
_journal_paper_doi               10.1039/d5ob00021a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C17 H14 Br F N2 O4'
_chemical_formula_sum            'C17 H14 Br F N2 O4'
_chemical_formula_weight         409.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-01-30 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                84.896(2)
_cell_angle_beta                 72.675(2)
_cell_angle_gamma                61.415(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9400(5)
_cell_length_b                   9.2953(5)
_cell_length_c                   11.9582(7)
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.506
_cell_measurement_theta_min      2.501
_cell_volume                     831.31(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            58517
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.658
_diffrn_reflns_theta_min         2.500
_exptl_absorpt_coefficient_mu    2.508
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1092 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.7311.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0485P)^2^+0.5711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3836
_reflns_number_total             5132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00021a3.cif
_cod_data_source_block           sgdp_373_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160371--7160372.cif.'
_cod_database_code               7160372
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.540
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C12(H12), C13(H13), C17(H17)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              44822
_olex2_submission_special_instructions 'No special instructions were received'