Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides
Panigrahi, Adyasha; Whitaker, Daniel; Vitorica-Yrezabal, Iñigo J.; Larrosa, Igor; ACS Catalysis  (2020) 2100–2107; doi:10.1021/acscatal.9b05334

data_4517337
_publ_section_title
;
 Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl
 Bromides
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2100
_journal_page_last               2107
_journal_paper_doi               10.1021/acscatal.9b05334
_journal_year                    2020
_chemical_formula_moiety         'C96 H156 Ag4 Br4 P4, 2(C H Cl3), [hexane]'
_chemical_formula_sum            'C104 H172 Ag4 Br4 Cl6 P4'
_chemical_formula_weight         2510.0
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.975(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.5364(5)
_cell_length_b                   15.9525(2)
_cell_length_c                   25.9141(5)
_cell_measurement_reflns_used    12735
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5670
_cell_measurement_theta_min      3.4200
_cell_volume                     10480.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -7.00  20.00   1.00    1.00    --    5.00  22.00  16.00   27
  2  \w    -80.00   1.00   1.00    1.00    --  -45.60  22.00  16.00   81
  3  \w    -82.00 -57.00   1.00    1.00    --  -45.60 -22.00-150.00   25
  4  \w   -192.00 -93.00   1.00    4.00    -- -107.20 -22.00-150.00   99
  5  \w   -108.00 -25.00   1.00    4.00    -- -107.20  22.00  16.00   83
  6  \w    -77.00  38.00   1.00    1.00    --  -45.60  57.00  60.00  115
  7  \w   -147.00 -49.00   1.00    4.00    -- -107.20  76.00   0.00   98
  8  \w   -145.00 -20.00   1.00    4.00    -- -107.20  76.00-180.00  125
  9  \w   -140.00 -19.00   1.00    4.00    -- -107.20  57.00-180.00  121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0005370000
_diffrn_orient_matrix_UB_12      -0.0112066000
_diffrn_orient_matrix_UB_13      -0.0592529000
_diffrn_orient_matrix_UB_21      -0.0586280000
_diffrn_orient_matrix_UB_22      0.0251767000
_diffrn_orient_matrix_UB_23      -0.0256164000
_diffrn_orient_matrix_UB_31      0.0158858000
_diffrn_orient_matrix_UB_32      0.0926196000
_diffrn_orient_matrix_UB_33      -0.0001980000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26578
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.158
_diffrn_reflns_theta_min         3.273
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    9.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       block
_exptl_crystal_F_000             4944
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.142
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         10462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+24.2750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9344
_reflns_number_total             10462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b05334_si_003.cif
_cod_data_source_block           s5524r
_cod_depositor_comments
'Adding full bibliography for 4517336--4517337.cif.'
_cod_database_code               4517337
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'AgBr C P'
_shelx_estimated_absorpt_t_max   0.609
_shelx_estimated_absorpt_t_min   0.398
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.a Ternary CH refined with riding coordinates:
 C27(H27), C3(H3), C37(H37), C29(H29), C32(H32), C5(H5), C18(H18), C8(H8),
 C39(H39), C15(H15), C42(H42), C13(H13), C49(H49)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C2(H2A,H2B), C30(H30A,H30B), C21(H21A,H21B), C6(H6A,H6B),
 C22(H22A,H22B), C31(H31A,H31B), C28(H28A,H28B), C9(H9A,H9B), C33(H33A,H33B),
 C45(H45A,H45B), C23(H23A,H23B), C46(H46A,H46B), C16(H16A,H16B), C4(H4A,H4B),
 C7(H7A,H7B), C36(H36A,H36B), C40(H40A,H40B), C20(H20A,H20B), C38(H38A,H38B),
 C41(H41A,H41B), C19(H19A,H19B), C12(H12A,H12B), C44(H44A,H44B), C17(H17A,H17B),
  C47(H47A,H47B), C34(H34A,H34B), C10(H10A,H10B), C14(H14A,H14B), C43(H43A,H43B)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              45692
_shelx_hkl_checksum              96894
_shelx_fab_checksum              14573
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.339
_oxdiff_exptl_absorpt_empirical_full_min 0.780