Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry
Takahashi, Rikuro; Seo, Tamae; Kubota, Koji; Ito, Hajime; ACS Catalysis  (2021) 14803–14810; doi:10.1021/acscatal.1c03731

data_4519144
_publ_section_title
;
 Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using
 Mechanochemistry
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14803
_journal_page_last               14810
_journal_paper_doi               10.1021/acscatal.1c03731
_journal_year                    2021
_chemical_formula_moiety         '2(C20 H3 F10)'
_chemical_formula_sum            'C40 H6 F20'
_chemical_formula_weight         866.45
_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     dual
_audit_creation_date             2021-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                82.0530(10)
_cell_angle_beta                 83.462(2)
_cell_angle_gamma                83.034(2)
_cell_formula_units_Z            2
_cell_length_a                   4.39520(10)
_cell_length_b                   18.1094(3)
_cell_length_c                   19.3056(3)
_cell_measurement_reflns_used    12497
_cell_measurement_temperature    123
_cell_measurement_theta_max      76.3720
_cell_measurement_theta_min      3.1590
_cell_volume                     1503.24(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.910
_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   -119.00 -62.00   0.50    2.70    --  -49.15  -9.00 100.00  114
  2  \w    -68.00 -41.00   0.50    2.70    --  -49.15 -57.00  60.00   54
  3  \w    -58.00 -32.00   0.50    2.70    --  -49.15 -68.00  37.70   52
  4  \w    -60.00 -34.00   0.50    2.70    --  -49.15 -62.00  25.62   52
  5  \w    -54.00 -28.00   0.50    2.70    --  -49.15 -77.00 -30.00   52
  6  \w    -57.00 -28.00   0.50    2.70    --  -49.15 -77.00 -60.00   58
  7  \w    -63.00 -36.00   0.50    2.70    --  -49.15 -57.00 -30.00   54
  8  \w    -61.00 -28.00   0.50    2.70    --  -49.15 -77.00   0.00   66
  9  \w    -71.00 -44.00   0.50    2.70    --  -49.15 -37.00  30.00   54
 10  \w    -11.00  21.00   0.50    2.70    --  -49.15  19.00  30.00   64
 11  \w    -64.00 -31.00   0.50    2.70    -- -102.00  57.00 -90.00   66
 12  \w   -112.00 -86.00   0.50    2.70    -- -102.00 -64.00  58.18   52
 13  \w   -105.00 -80.00   0.50    2.70    -- -102.00 -82.00  74.69   50
 14  \w   -109.00 -83.00   0.50    2.70    -- -102.00 -73.00  36.15   52
 15  \w   -112.00 -87.00   0.50    2.70    -- -102.00 -62.00  31.78   50
 16  \w   -106.00 -81.00   0.50    2.70    -- -102.00 -77.00  30.00   50
 17  \w   -110.00 -81.00   0.50    2.70    -- -102.00 -77.00  60.00   58
 18  \w   -106.00 -80.00   0.50    2.70    -- -102.00 -80.00  86.75   52
 19  \w   -108.00 -81.00   0.50    2.70    -- -102.00 -78.00  23.82   54
 20  \w   -108.00 -81.00   0.50    2.70    -- -102.00 -77.00 -30.00   54
 21  \w   -108.00 -82.00   0.50    2.70    -- -102.00 -76.00  -4.56   52
 22  \w   -108.00 -81.00   0.50    2.70    -- -102.00 -77.00 -13.87   54
 23  \w   -108.00 -82.00   0.50    2.70    -- -102.00 -75.00 -42.81   52
 24  \w   -106.00 -80.00   0.50    2.70    -- -102.00 -82.00 -45.53   52
 25  \w   -111.00 -85.00   0.50    2.70    -- -102.00 -68.00 -32.04   52
 26  \w   -116.00 -89.00   0.50    2.70    -- -102.00 -57.00 -60.00   54
 27  \w   -108.00 -83.00   0.50    2.70    -- -102.00 -73.00 -61.70   50
 28  \w   -108.00 -81.00   0.50    2.70    -- -102.00 -77.00   0.00   54
 29  \w   -108.00 -83.00   0.50    2.70    -- -102.00 -73.00  41.40   50
 30  \w   -108.00 -81.00   0.50    2.70    -- -102.00 -77.00  90.00   54
 31  \w   -107.00 -82.00   0.50    2.70    -- -102.00 -78.00  39.18   50
 32  \w   -107.00 -81.00   0.50    2.70    -- -102.00 -78.00  27.30   52
 33  \w   -116.00 -85.00   0.50    2.70    -- -102.00 -67.00  82.40   62
 34  \w   -121.00 -84.00   0.50    2.70    -- -102.00 -70.00   3.29   74
 35  \w   -114.00 -88.00   0.50    2.70    -- -102.00 -59.00 -49.25   52
 36  \w   -116.00 -86.00   0.50    2.70    -- -102.00 -65.00 -22.98   60
 37  \w   -123.00 -88.00   0.50    2.70    -- -102.00 -59.00  55.26   70
 38  \w   -118.00 -82.00   0.50    2.70    -- -102.00 -74.00  98.37   72
 39  \w   -138.00 -89.00   0.50    2.70    -- -102.00 -57.00  30.00   98
 40  \w   -149.00-114.00   0.50    2.70    -- -102.00 -77.00  30.00   70
 41  \w   -151.00 -85.00   0.50    2.70    -- -102.00 -68.00 105.17  132
 42  \w   -167.00-130.00   0.50    2.70    -- -102.00 -59.00  55.26   74
 43  \w   -172.00-129.00   0.50    2.70    -- -102.00  -9.00 100.00   86
 44  \w   -167.00-142.00   0.50    2.70    -- -102.00 -62.00  31.78   50
 45  \w   -173.00 -89.00   0.50    2.70    -- -102.00 -56.00   7.48  168
 46  \w   -167.00-141.00   0.50    2.70    -- -102.00 -80.00  86.75   52
 47  \w   -173.00-114.00   0.50    2.70    -- -102.00 -82.00  74.69  118
 48  \w   -174.00 -88.00   0.50    2.70    -- -102.00 -62.00  -9.77  172
 49  \w   -170.00-143.00   0.50    2.70    -- -102.00 -73.00 -61.70   54
 50  \w   -172.00 -95.00   0.50    2.70    -- -102.00 -37.00 -90.00  154
 51  \w   -173.00-148.00   0.50    2.70    -- -102.00 -77.00 -30.00   50
 52  \w   -173.00-147.00   0.50    2.70    -- -102.00 -77.00 -13.87   52
 53  \w   -173.00-145.00   0.50    2.70    -- -102.00 -76.00  -4.56   56
 54  \w     24.00  94.00   0.50    2.70    --   49.15-125.00 -60.00  140
 55  \w     36.00 108.00   0.50    2.70    --  102.75-125.00  30.00  144
 56  \w     41.00 105.00   0.50    2.70    --  102.75 -99.00  60.00  128
 57  \w     41.00 107.00   0.50    2.70    --   49.15   9.00 -84.00  132
 58  \w    127.00 152.00   0.50    2.70    --  102.75   9.00 -84.00   50
 59  \w    149.00 174.00   0.50    2.70    --  102.75  77.00 -30.00   50
 60  \w    129.00 154.00   0.50    2.70    --  102.75  77.00  60.00   50
 61  \w     82.00 109.00   0.50    2.70    --  102.75  77.00 -60.00   54
 62  \w     83.00 108.00   0.50    2.70    --  102.75  77.00   0.00   50
 63  \w     84.00 109.00   0.50    2.70    --  102.75  77.00  60.00   50
 64  \w     83.00 108.00   0.50    2.70    --  102.75  77.00 -30.00   50
 65  \w     82.00 109.00   0.50    2.70    --  102.75  77.00 -90.00   54
 66  \w     41.00  68.00   0.50    2.70    --   49.15  57.00  30.00   54
 67  \w     42.00 106.00   0.50    2.70    --   49.15  19.00  30.00  128
 68  \w     49.00  76.00   0.50    2.70    --   49.15  37.00 -60.00   54
 69  \w     32.00  71.00   0.50    2.70    --   49.15  77.00 -30.00   78
 70  \w     32.00  57.00   0.50    2.70    --   49.15  77.00   0.00   50
 71  \w     31.00  57.00   0.50    2.70    --   49.15  77.00  60.00   52
 72  \w     31.00  58.00   0.50    2.70    --   49.15  77.00  90.00   54
 73  \w     31.00  56.00   0.50    2.70    --   49.15  77.00  30.00   50
 74  \w     34.00  66.00   0.50    2.70    --  102.75 -57.00 -60.00   64
 75  \w     44.00 101.00   0.50    2.70    --  102.75 -99.00 -60.00  114
 76  \w     41.00  80.00   0.50    2.70    --  102.75 -99.00  30.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0050377000
_diffrn_orient_matrix_UB_12      0.0848371000
_diffrn_orient_matrix_UB_13      0.0023005000
_diffrn_orient_matrix_UB_21      -0.0289697000
_diffrn_orient_matrix_UB_22      -0.0134724000
_diffrn_orient_matrix_UB_23      0.0809226000
_diffrn_orient_matrix_UB_31      0.3537051000
_diffrn_orient_matrix_UB_32      -0.0091874000
_diffrn_orient_matrix_UB_33      -0.0013580000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30266
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.514
_diffrn_reflns_theta_min         2.322
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (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    1.914
_exptl_crystal_description       needle
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         5776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0716P)^2^+2.2264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4608
_reflns_number_total             5776
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 4.3132\% 
 around [0.09 0.87 -0.49] (reciprocal) or [0.77 0.53 -0.34] (direct)
;
_cod_data_source_file            cs1c03731_si_002.cif
_cod_data_source_block           rik-805_twin1_hklf4
_cod_database_code               4519144
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H F'
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.661
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C015(H015), C016(H016), C019(H019), C01C(H01C), C01I(H01I), C01L(H01L)
;
_shelx_res_checksum              40796
_shelx_hkl_checksum              48798
_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 2.081
_oxdiff_exptl_absorpt_empirical_full_min 0.687
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2