Ring expansion of 3-hydroxyoxindoles to 4-quinolones <i>via</i> palladium-catalyzed C-C(acyl) bond cleavage.
Huang, Zhi-Cong; Ruan, Zhi-Ling; Xu, Hui; Dai, Hui-Xiong; Chemical communications (Cambridge, England) 61 (2024) 109–112; doi:10.1039/d4cc05369a

data_7133999
_publ_section_title
;
 Ring expansion of 3-hydroxyoxindoles to 4-quinolones <i>via</i>
 palladium-catalyzed C-C(acyl) bond cleavage.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              109
_journal_page_last               112
_journal_paper_doi               10.1039/d4cc05369a
_journal_volume                  61
_journal_year                    2024
_chemical_formula_moiety         '2(C18 H14 F3 N O)'
_chemical_formula_sum            'C36 H28 F6 N2 O2'
_chemical_formula_weight         634.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-08 deposited with the CCDC.	2024-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.784(2)
_cell_length_b                   6.9333(6)
_cell_length_c                   16.7815(18)
_cell_measurement_reflns_used    1806
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.587
_cell_measurement_theta_min      2.426
_cell_volume                     3000.0(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17528
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         1.992
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.0452
_exptl_absorpt_correction_T_min  0.0233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1061 before and 0.0505 after correction. The Ratio of minimum to maximum transmission is 0.5155. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3262
_refine_ls_number_restraints     312
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0741P)^2^+1.5389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1651
_reflns_number_total             3262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05369a2.cif
_cod_data_source_block           dd
_cod_depositor_comments          'Adding full bibliography for 7133999.cif.'
_cod_database_code               7133999
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H1A,H1B,H1C} of C1
 At 1.5 times of:
  {H24A,H24B,H24C} of C24, {H9A,H9B,H9C} of C9, {H26A,H26B,H26C} of C26
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H24A(0.5)
 H24B(0.5) H24C(0.5) H26A(0.5) H26B(0.5) H26C(0.5) F5(0.5) F3(0.5) F4(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C18(H18), C19(H19), C3(H3), C20(H20), C12(H12), C13(H13), C5(H5),
 C00W(H00W), C4(H4), C28(H28), C29(H29)
4.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'