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_4517336
_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         'C28 H39 Ag F9 O P'
_chemical_formula_sum            'C28 H39 Ag F9 O P'
_chemical_formula_weight         701.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81790(10)
_cell_length_b                   14.10410(10)
_cell_length_c                   20.6209(2)
_cell_measurement_reflns_used    26289
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7850
_cell_measurement_theta_min      2.1770
_cell_volume                     2812.24(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.970
_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    -28.00  39.00   1.00    1.00    --    5.00 -76.00-180.00   67
  2  \w    -86.00  42.00   1.00    1.00    --  -45.60  76.00   0.00  128
  3  \w   -132.00 -88.00   1.00    1.00    --  -45.60 -76.00 -30.00   44
  4  \w    -72.00  44.00   1.00    1.00    --  -45.60  38.00-180.00  116
  5  \w     -1.00  24.00   1.00    1.00    --  -45.60  57.00 -30.00   25
  6  \w    -30.00  43.00   1.00    1.00    --  -45.60  57.00  60.00   73
  7  \w    -52.00  -6.00   1.00    1.00    --  -45.60 -76.00 -30.00   46
  8  \w   -193.00 -74.00   1.00    1.00    -- -107.20 -57.00-120.00  119
  9  \w   -125.00 -97.00   1.00    1.00    -- -107.20 -76.00 120.00   28
 10  \w   -196.00 -71.00   1.00    1.00    -- -107.20 -67.00 -23.83  125
 11  \w   -147.00 -60.00   1.00    1.00    -- -107.20  76.00  90.00   87
 12  \w    -96.00 -69.00   1.00    1.00    -- -107.20 -76.00   0.00   27
 13  \w   -168.00 -84.00   1.00    1.00    -- -107.20 -76.00-150.00   84
 14  \w   -195.00 -79.00   1.00    1.00    -- -107.20 -57.00 -90.00  116
 15  \w    -44.00 -18.00   1.00    1.00    -- -107.20  76.00 120.00   26
 16  \w    -92.00 -67.00   1.00    1.00    -- -107.20 -76.00   7.80   25
 17  \w   -142.00 -47.00   1.00    1.00    -- -107.20  76.00 120.00   95
 18  \w    -44.00 -19.00   1.00    1.00    -- -107.20  76.00  60.00   25
 19  \w    -53.00 -27.00   1.00    1.00    -- -107.20  76.00 -60.00   26
 20  \w   -180.00-104.00   1.00    1.00    -- -107.20 -76.00  30.00   76
 21  \w    -99.00 -67.00   1.00    1.00    -- -107.20 -76.00  30.00   32
 22  \w   -183.00-157.00   1.00    1.00    -- -107.20 -76.00 120.00   26
 23  \w    -92.00 -67.00   1.00    1.00    -- -107.20  76.00 -60.00   25
 24  \w   -148.00 -73.00   1.00    1.00    -- -107.20  76.00  60.00   75
 25  \w    -93.00 -68.00   1.00    1.00    -- -107.20 -74.00 -23.21   25
 26  \w    -95.00 -70.00   1.00    1.00    -- -107.20 -71.00  12.67   25
 27  \w   -190.00 -71.00   1.00    1.00    -- -107.20 -69.00   6.61  119
 28  \w   -134.00 -62.00   1.00    1.00    -- -107.20  76.00-180.00   72
 29  \w   -175.00-150.00   1.00    1.00    -- -107.20 -71.00  12.67   25
;
_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      -0.0387737000
_diffrn_orient_matrix_UB_12      0.1028536000
_diffrn_orient_matrix_UB_13      -0.0203701000
_diffrn_orient_matrix_UB_21      0.1496418000
_diffrn_orient_matrix_UB_22      0.0187220000
_diffrn_orient_matrix_UB_23      -0.0098900000
_diffrn_orient_matrix_UB_31      -0.0384544000
_diffrn_orient_matrix_UB_32      -0.0316331000
_diffrn_orient_matrix_UB_33      -0.0724150000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31665
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.246
_diffrn_reflns_theta_min         4.354
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    7.028
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         5724
_refine_ls_number_restraints     280
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0308P)^2^+4.6891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5704
_reflns_number_total             5724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b05334_si_002.cif
_cod_data_source_block           s5523r
_cod_depositor_comments
'Adding full bibliography for 4517336--4517337.cif.'
_cod_database_code               4517336
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.307
_shelx_estimated_absorpt_t_min   0.227
_diffrn_oxdiff_digest_frames
;
0116a0af93c531d4a12d5528c5997bf9e400034d9c2
;
_diffrn_oxdiff_digest_hkl
;
01c53ccda5b7ce0f12c9c54fd4a43804cd0d7a
;
_reflns_odcompleteness_completeness 98.66
_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. Restrained distances
 F18-F17
 2.36 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F4 \\sim F1 \\sim F5 \\sim F7 \\sim F8 \\sim F6 \\sim F2 \\sim F3 \\sim F9
\\sim F16 \\sim F17 \\sim F10 \\sim F11 \\sim F13 \\sim F14 \\sim F18 \\sim F12
\\sim F15: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
F13 \\sim F1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 Ag1, F4, F1, F5, F7, F8, F6, F2, F3, O1, F16, F17, F10, F11, F13, F14, F18,
 F15, C25, C26, C27, C28, C29, C30, C31
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Fixed Sof: F4(0.825) F1(0.825) F5(0.825) F7(0.825) F8(0.825) F6(0.825)
 F2(0.825) F3(0.825) F9(0.825) F16(0.175) F17(0.175) F10(0.175) F11(0.175)
 F13(0.175) F14(0.175) F18(0.175) F12(0.175) F15(0.175) C26(0.825) C27(0.825)
 C28(0.825) C29(0.175) C30(0.175) C31(0.175)
6.a Ternary CH refined with riding coordinates:
 C13(H13), C3(H3), C18(H18), C15(H15), C5(H5), C8(H8)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C2(H2A,H2B), C14(H14A,H14B), C7(H7A,H7B),
 C17(H17A,H17B), C4(H4A,H4B), C6(H6A,H6B), C21(H21A,H21B), C23(H23A,H23B),
 C9(H9A,H9B), C22(H22A,H22B), C16(H16A,H16B), C20(H20A,H20B), C10(H10A,H10B)
6.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              79811
_shelx_hkl_checksum              90517
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.769