Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.
White, Paul B.; Jaworski, Jonathan N.; Zhu, Geyunjian Harry; Stahl, Shannon S.; ACS catalysis 6 (2016) 3340–3348; doi:10.1021/acscatal.6b00953

data_4513870
_publ_section_title
;
 Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of
 Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.
;
_journal_issue                   5
_journal_name_full               'ACS catalysis'
_journal_page_first              3340
_journal_page_last               3348
_journal_paper_doi               10.1021/acscatal.6b00953
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C22 H23 N3 O4 Pd'
_chemical_formula_sum            'C22 H23 N3 O4 Pd'
_chemical_formula_weight         499.83
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.22(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.472(6)
_cell_length_b                   8.829(5)
_cell_length_c                   19.260(8)
_cell_measurement_reflns_used    6033
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      2.54
_cell_volume                     2120.8(18)
_computing_cell_refinement       'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_data_collection       'APEX2 Ver. 2013.2-0 (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008-2013)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008-2013)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008-2013)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008-2013)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.5\ \w and 0.5\ \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19478
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.656
_diffrn_reflns_theta_min         1.633
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.9345.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.078
_refine_diff_density_max         1.554
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         6447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0315P)^2^+0.5420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5351
_reflns_number_total             6447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00953_si_002.cif
_cod_data_source_block           Pd(k1-Me2DAF)(py)(OAc)2
_cod_depositor_comments
'Adding full bibliography for 4513868--4513870.cif.'
_cod_original_cell_volume        2120.8(19)
_cod_database_code               4513870
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.759
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              8631
_shelx_hkl_checksum              69228