Anion Ligand Promoted Selective C-F Bond Reductive Elimination Enables C(sp2)-H Fluorination
Mao, Yang-Jie; Luo, Gen; Hao, Hong-Yan; Xu, Zhen Yuan; Lou, Shao-Jie; Xu, Dan-Qian; Chemical Communications  (2019) –; doi:10.1039/C9CC07726J

data_7124448
_publ_section_title
;
 Anion Ligand Promoted Selective C-F Bond Reductive Elimination Enables
 C(sp2)-H Fluorination
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07726J
_journal_year                    2019
_chemical_formula_moiety         '2(C14 H12 N4 O3 Pd), C H2 Cl2'
_chemical_formula_sum            'C29 H26 Cl2 N8 O6 Pd2'
_chemical_formula_weight         866.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2019-08-23 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9255(13)
_cell_length_b                   7.4483(7)
_cell_length_c                   18.7126(11)
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3451
_cell_measurement_theta_min      2.8586
_cell_volume                     3334.7(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -62.00   36.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8433  -38.0000  -60.0000 98

  2 omega  -15.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8433   38.0000  120.0000 91

  3 omega  -70.00   21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621  -77.0000 -180.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0037065000
_diffrn_orient_matrix_UB_12      -0.0157815000
_diffrn_orient_matrix_UB_13      0.0370666000
_diffrn_orient_matrix_UB_21      0.0105932000
_diffrn_orient_matrix_UB_22      -0.0883093000
_diffrn_orient_matrix_UB_23      -0.0042774000
_diffrn_orient_matrix_UB_31      0.0274326000
_diffrn_orient_matrix_UB_32      0.0319734000
_diffrn_orient_matrix_UB_33      0.0067229000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19430
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.864
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_description       block
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         2.500
_refine_diff_density_min         -1.623
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0652P)^2^+15.8201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2195
_reflns_number_total             3047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07726j2.cif
_cod_data_source_block           170301_myj20170227_1
_cod_database_code               7124448
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 pd1'
_shelx_estimated_absorpt_t_max   0.682
_shelx_estimated_absorpt_t_min   0.576
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: H15A(0.5) H15B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              11363
_olex2_submission_special_instructions 'No special instructions were received'