Electronically flexible PYA ligands for efficient palladium-catalyzed α-arylation of ketones
Reusser, Esaie; Albrecht, Martin; Dalton Transactions  (2023) –; doi:10.1039/D3DT03182A

data_7714251
_publ_section_title
;
 Electronically flexible PYA ligands for efficient palladium-catalyzed
 \a-arylation of ketones
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT03182A
_journal_year                    2023
_chemical_formula_moiety         'F6 P, C13 H14 N3 O'
_chemical_formula_sum            'C13 H14 F6 N3 O P'
_chemical_formula_weight         373.24
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-13T21:43:23-00:00
_audit_update_record
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6664(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   21.02657(6)
_cell_length_b                   14.43623(4)
_cell_length_c                   21.17731(6)
_cell_measurement_reflns_used    172172
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      79.856
_cell_measurement_theta_min      2.975
_cell_volume                     6427.82(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_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    -95.00  -6.00   0.50    0.40    --  -23.00 -63.00 -56.00  178
  2  \w    -40.00  50.00   0.50    0.40    --  -23.00  63.00  81.00  180
  3  \w     31.00 121.00   0.50    0.40    --   47.92  63.00  81.00  180
  4  \w     96.00 177.00   0.50    1.50    --  113.25  63.00  81.00  162
  5  \w     42.00  71.00   0.50    1.50    --  113.25 -63.00 -56.00   58
  6  \w    -94.00  -8.00   0.50    0.40    --  -23.00 -57.00 120.00  172
  7  \w     -7.00  23.00   0.50    0.40    --   26.00  99.00 -98.25   60
  8  \w      4.00  34.00   0.50    0.40    --   34.00  93.00  72.30   60
  9  \w     13.00  42.00   0.50    0.40    --   42.00  91.00 -43.67   58
 10  \w     17.00  43.00   0.50    0.40    --   46.00  90.00  73.93   52
 11  \w     17.00  43.00   0.50    0.40    --   46.00  90.00-161.81   52
 12  \w     17.00  43.00   0.50    0.40    --   46.00  90.00 158.81   52
 13  \w     17.00  43.00   0.50    0.40    --   46.00  90.00  22.06   52
 14  \w     -1.00  81.00   0.50    0.40    --   47.92 -99.00 -90.00  164
 15  \w    -24.00  65.00   0.50    0.40    --   47.92 -63.00 -56.00  178
 16  \w     27.00 122.00   0.50    0.40    --   50.00  77.00 -80.16  190
 17  \w     32.00 126.00   0.50    0.40    --   54.00  76.00 -30.31  188
 18  \w     31.00 126.00   0.50    0.40    --   54.00  77.00  39.39  190
 19  \w     40.00 135.00   0.50    0.40    --   62.00  76.00 -69.56  190
 20  \w     45.00 139.00   0.50    0.40    --   66.00  73.00 -88.95  188
 21  \w     43.00 139.00   0.50    0.40    --   66.00  77.00 165.06  192
 22  \w     44.00 139.00   0.50    0.40    --   66.00  76.00  69.80  190
 23  \w     43.00 139.00   0.50    0.40    --   66.00  77.00 103.44  192
 24  \w     44.00 139.00   0.50    0.40    --   66.00  76.00-136.13  190
 25  \w     47.00 143.00   0.50    0.40    --   70.00  77.00  42.97  192
 26  \w     48.00 143.00   0.50    0.40    --   70.00  76.00  10.94  190
 27  \w     48.00 143.00   0.50    0.40    --   70.00  76.00-122.20  190
 28  \w     48.00 143.00   0.50    0.40    --   70.00  75.00 -16.98  190
 29  \w     48.00 143.00   0.50    0.40    --   70.00  75.00 -53.56  190
 30  \w     47.00 143.00   0.50    0.40    --   70.00  77.00-168.53  192
 31  \w     48.00 143.00   0.50    0.40    --   70.00  76.00 126.72  190
 32  \w     57.00 146.00   0.50    0.40    --   74.00  62.00  86.98  178
 33  \w     51.00 146.00   0.50    0.40    --   74.00  77.00  19.63  190
 34  \w     59.00 151.00   0.50    0.40    --   78.00  69.00 162.40  184
 35  \w     66.00 154.00   0.50    1.50    --   82.00  60.00-120.80  176
 36  \w     72.00 162.00   0.50    1.50    --   90.00  65.00-123.37  180
 37  \w     68.00 162.00   0.50    1.50    --   90.00  75.00  15.84  188
 38  \w     74.00 162.00   0.50    1.50    --   90.00  60.00 -73.67  176
 39  \w    122.00 148.00   0.50    1.50    --   94.00  77.00   0.46   52
 40  \w     71.00 118.00   0.50    1.50    --   94.00  77.00   0.46   94
 41  \w    131.00 162.00   0.50    1.50    --   94.00  74.00 162.82   62
 42  \w     73.00  98.00   0.50    1.50    --   94.00  74.00 162.82   50
 43  \w     33.00  99.00   0.50    1.50    --  102.00 -80.00  80.79  132
 44  \w     97.00 133.00   0.50    1.50    --  113.25  61.00-120.00   72
 45  \w    131.00 166.00   0.50    1.50    --  113.25  77.00 -30.00   70
 46  \w     80.00 106.00   0.50    1.50    --  113.25 -94.00-150.00   52
 47  \w     91.00 123.00   0.50    1.50    --  113.25  77.00 -30.00   64
 48  \w    123.00 176.00   0.50    1.50    --  113.25  77.00 -60.00  106
 49  \w    152.00 177.00   0.50    1.50    --  113.25  77.00-120.00   50
 50  \w     44.00  69.00   0.50    1.50    --  113.25 -94.00-150.00   50
 51  \w     42.00  72.00   0.50    1.50    --  113.25 -94.00  30.00   60
 52  \w     92.00 118.00   0.50    1.50    --  113.25  77.00 150.00   52
 53  \w    125.00 174.00   0.50    1.50    --  113.25  77.00 150.00   98
 54  \w     97.00 174.00   0.50    1.50    --  113.25  61.00 -30.00  154
 55  \w     91.00 117.00   0.50    1.50    --  113.25  77.00 -60.00   52
 56  \w     46.00 105.00   0.50    1.50    --  113.25 -94.00  60.00  118
 57  \w     91.00 141.00   0.50    1.50    --  113.25  77.00-120.00  100
 58  \w    136.00 168.00   0.50    1.50    --  113.25  61.00-120.00   64
 59  \w     46.00 102.00   0.50    1.50    --  113.25 -77.00 -90.00  112
 60  \w    135.00 177.00   0.50    1.50    --  113.25  77.00 -90.00   84
 61  \w     97.00 159.00   0.50    1.50    --  113.25  61.00  30.00  124
 62  \w     91.00 117.00   0.50    1.50    --  113.25  77.00 -90.00   52
 63  \w    131.00 162.00   0.50    1.50    --  113.25  61.00  60.00   62
 64  \w    136.00 174.00   0.50    1.50    --  113.25  77.00  90.00   76
 65  \w     42.00 105.00   0.50    1.50    --  113.25 -94.00 -30.00  126
 66  \w     91.00 118.00   0.50    1.50    --  113.25  77.00   0.00   54
 67  \w     97.00 123.00   0.50    1.50    --  113.25  61.00  60.00   52
 68  \w     91.00 148.00   0.50    1.50    --  113.25  77.00 120.00  114
 69  \w     91.00 125.00   0.50    1.50    --  113.25  77.00  90.00   68
 70  \w     42.00 106.00   0.50    1.50    --  113.25 -94.00 -90.00  128
 71  \w     78.00 105.00   0.50    1.50    --  113.25 -94.00 120.00   54
 72  \w     97.00 165.00   0.50    1.50    --  113.25  61.00 -90.00  136
 73  \w     80.00 106.00   0.50    1.50    --  113.25 -94.00 150.00   52
 74  \w     97.00 123.00   0.50    1.50    --  113.25  61.00 150.00   52
 75  \w     98.00 164.00   0.50    1.50    --  113.25  61.00 -60.00  132
 76  \w     97.00 122.00   0.50    1.50    --  113.25  61.00  90.00   50
 77  \w    133.00 159.00   0.50    1.50    --  113.25  61.00-150.00   52
 78  \w    128.00 176.00   0.50    1.50    --  113.25  77.00-150.00   96
 79  \w     97.00 122.00   0.50    1.50    --  113.25  61.00-150.00   50
 80  \w    138.00 177.00   0.50    1.50    --  113.25  77.00  30.00   78
 81  \w    126.00 158.00   0.50    1.50    --  113.25  61.00 150.00   64
 82  \w     44.00  70.00   0.50    1.50    --  113.25 -94.00 120.00   52
 83  \w     91.00 120.00   0.50    1.50    --  113.25  77.00-150.00   58
 84  \w     94.00 133.00   0.50    1.50    --  113.25  77.00  30.00   78
 85  \w     73.00 105.00   0.50    1.50    --  113.25 -94.00   0.00   64
 86  \w     42.00  68.00   0.50    1.50    --  113.25 -94.00   0.00   52
 87  \w     42.00  67.00   0.50    1.50    --  113.25 -61.00-150.00   50
 88  \w    137.00 175.00   0.50    1.50    --  113.25  63.00-169.31   76
 89  \w    137.00 173.00   0.50    1.50    --  113.25  61.00-180.00   72
 90  \w     43.00 100.00   0.50    1.50    --  113.25 -77.00 120.00  114
 91  \w     97.00 123.00   0.50    1.50    --  113.25  61.00-180.00   52
 92  \w     96.00 132.00   0.50    1.50    --  113.25  63.00-169.31   72
 93  \w     43.00  85.00   0.50    1.50    --  113.25 -77.00  90.00   84
 94  \w     42.00 106.00   0.50    1.50    --  113.25 -99.00-117.15  128
 95  \w     44.00 102.00   0.50    1.50    --  113.25 -77.00 150.00  116
 96  \w     42.00  67.00   0.50    1.50    --  113.25 -61.00  30.00   50
 97  \w     97.00 171.00   0.50    1.50    --  113.25  61.00   0.00  148
 98  \w    127.00 173.00   0.50    1.50    --  113.25  77.00  60.00   92
 99  \w     91.00 117.00   0.50    1.50    --  113.25  77.00  60.00   52
100  \w     97.00 170.00   0.50    1.50    --  113.25  61.00 120.00  146
101  \w     76.00 106.00   0.50    1.50    --  113.25 -94.00  30.00   60
102  \w    122.00 148.00   0.50    1.50    --  113.25  77.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0491387
_diffrn_orient_matrix_UB_12      -0.0251555
_diffrn_orient_matrix_UB_13      0.051698
_diffrn_orient_matrix_UB_21      -0.0347942
_diffrn_orient_matrix_UB_22      -0.0922732
_diffrn_orient_matrix_UB_23      0.0114517
_diffrn_orient_matrix_UB_31      0.0417805
_diffrn_orient_matrix_UB_32      -0.0472967
_diffrn_orient_matrix_UB_33      -0.0498859
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            246423
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.994
_diffrn_reflns_theta_min         2.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.208
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.58692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             3040
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1090
_refine_ls_number_reflns         13039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+4.0916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0
_reflns_number_gt                12544
_reflns_number_total             13039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03182a2.cif
_cod_data_source_block           22MA012_ER-0182
_cod_database_code               7714251
_shelx_estimated_absorpt_t_min   0.449
_shelx_estimated_absorpt_t_max   0.658
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.474
_oxdiff_exptl_absorpt_empirical_full_min 0.647
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              2284