In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides.
Milner, Phillip J.; Yang, Yang; Buchwald, Stephen L.; Organometallics 34 (2015) 4775–4780; doi:10.1021/acs.organomet.5b00631

data_4087825
_publ_section_title
;
 In-Depth Assessment of the Palladium-Catalyzed Fluorination of
 Five-Membered Heteroaryl Bromides.
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4775
_journal_page_last               4780
_journal_paper_doi               10.1021/acs.organomet.5b00631
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C52 H72 Br Cl6 O3 P Pd S'
_chemical_formula_weight         1207.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                70.077(4)
_cell_angle_beta                 77.005(4)
_cell_angle_gamma                62.377(3)
_cell_formula_units_Z            2
_cell_length_a                   13.5389(7)
_cell_length_b                   14.0092(8)
_cell_length_c                   17.1535(11)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.12
_cell_measurement_theta_min      3.70
_cell_volume                     2701.4(3)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            72957
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         2.749
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    7.324
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1244
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.005
_refine_diff_density_max         3.273
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         9735
_refine_ls_number_restraints     1134
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0720P)^2^+23.5501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1710
_refine_ls_wR_factor_ref         0.1784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8532
_reflns_number_total             9735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00631_si_002.cif
_cod_data_source_block           X14114
_cod_database_code               4087825
_shelx_estimated_absorpt_t_min   0.196
_shelx_estimated_absorpt_t_max   0.964
_shelxl_version_number           2014-2
_shelx_res_checksum              26736
_shelx_hkl_checksum              64647