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_7124449
_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         'C14 H12 N4 O2 Pd, H2 O'
_chemical_formula_sum            'C14 H14 N4 O3 Pd'
_chemical_formula_weight         392.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-08-23 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.8026(6)
_cell_length_b                   4.69190(10)
_cell_length_c                   20.2989(4)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      60.648
_cell_measurement_theta_min      4.878
_cell_volume                     3158.71(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      302.25
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19305
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.617
_diffrn_reflns_theta_min         4.876
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.429
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.4874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1598 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.6482. The \l/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_refine_diff_density_max         0.538
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+3.5513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2721
_reflns_number_total             3586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07726j2.cif
_cod_data_source_block           mjr17026_0m
_cod_database_code               7124449
_shelx_shelxl_version_number     2017/1
_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, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.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)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              70779
_olex2_submission_special_instructions 'No special instructions were received'