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_4513869
_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         'C20 H17 N3 O5 Pd'
_chemical_formula_sum            'C20 H17 N3 O5 Pd'
_chemical_formula_weight         485.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-01
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.01.25 svn.r3250 for OlexSys, GUI svn.r5148)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.713(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.060(3)
_cell_length_b                   10.703(4)
_cell_length_c                   15.879(5)
_cell_measurement_reflns_used    9706
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.585
_cell_measurement_theta_min      2.313
_cell_volume                     1833.6(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 Ver. 2012.14-3 (Bruker-AXS, 2012)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49989
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.626
_diffrn_reflns_theta_min         2.049
_diffrn_source_type              'Incoatec I\ms'
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_exptl_absorpt_correction_T_max  0.9652
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1123 before and 0.0383 after correction.
The Ratio of minimum to maximum transmission is 0.8554.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.985
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0219
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+1.5509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5258
_reflns_number_total             5569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00953_si_002.cif
_cod_data_source_block           Pd(k1-DAF)(py)(OAc)2
_cod_depositor_comments
'Adding full bibliography for 4513868--4513870.cif.'
_cod_original_cell_volume        1833.7(10)
_cod_database_code               4513869
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.773
_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. Uiso/Uaniso restraints and constraints
Uanis(O5) = Uanis(O5A)
3. Others
 Sof(O5A)=1-FVAR(1)
 Sof(O5)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
4.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              65093
_shelx_hkl_checksum              1145
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'