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

data_7714252
_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         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-26T16:09:13-00:00
_audit_update_record
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5286(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.25664(8)
_cell_length_b                   9.94244(8)
_cell_length_c                   11.26378(9)
_cell_measurement_reflns_used    18371
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      79.55
_cell_measurement_theta_min      4.299
_cell_volume                     1148.227(16)
_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    -42.00  50.00   0.50    0.22    --  -23.00  67.00  61.00  184
  2  \w    -95.00  -4.00   0.50    0.22    --  -23.00 -67.00 -72.00  182
  3  \w     29.00 120.00   0.50    0.22    --   47.95  67.00  61.00  182
  4  \w     95.00 177.00   0.50    1.00    --  113.25  67.00  61.00  164
  5  \w     42.00  78.00   0.50    1.00    --  113.25 -67.00 -72.00   72
  6  \w    -95.00 -10.00   0.50    0.22    --  -23.00 -45.00 120.00  170
  7  \w    -70.00 -12.00   0.50    0.22    --  -23.00 125.00-180.00  116
  8  \w    -24.00  67.00   0.50    0.22    --   47.95 -67.00 -72.00  182
  9  \w    -26.00  23.00   0.50    0.22    --   47.95 -19.00 120.00   98
 10  \w     36.00 121.00   0.50    0.22    --   47.95  38.00  30.00  170
 11  \w     97.00 177.00   0.50    1.00    --  113.25  61.00 -60.00  160
 12  \w     97.00 177.00   0.50    1.00    --  113.25  61.00 150.00  160
 13  \w     42.00  68.00   0.50    1.00    --  113.25 -61.00  90.00   52
 14  \w     42.00 106.00   0.50    1.00    --  113.25 -94.00  30.00  128
 15  \w     97.00 177.00   0.50    1.00    --  113.25  61.00   0.00  160
 16  \w     91.00 177.00   0.50    1.00    --  113.25  77.00 -90.00  172
 17  \w     42.00 102.00   0.50    1.00    --  113.25 -77.00 -90.00  120
 18  \w     97.00 177.00   0.50    1.00    --  113.25  61.00  30.00  160
 19  \w     97.00 177.00   0.50    1.00    --  113.25  61.00 -30.00  160
 20  \w    101.00 177.00   0.50    1.00    --  113.25  45.00   0.00  152
 21  \w     95.00 177.00   0.50    1.00    --  113.25  67.00  13.92  164
 22  \w    101.00 177.00   0.50    1.00    --  113.25  30.00 -30.00  152
 23  \w    107.00 177.00   0.50    1.00    --  113.25 101.00-106.78  140
 24  \w     91.00 177.00   0.50    1.00    --  113.25  77.00 -30.00  172
 25  \w     91.00 177.00   0.50    1.00    --  113.25  77.00 -60.00  172
 26  \w     42.00  68.00   0.50    1.00    --  113.25 -61.00 -30.00   52
 27  \w     42.00 102.00   0.50    1.00    --  113.25 -77.00-120.00  120
 28  \w    100.00 177.00   0.50    1.00    --  113.25  15.00  90.00  154
 29  \w     42.00  68.00   0.50    1.00    --  113.25 -61.00 -60.00   52
 30  \w     42.00 106.00   0.50    1.00    --  113.25 -94.00-180.00  128
 31  \w     42.00 106.00   0.50    1.00    --  113.25 -94.00  90.00  128
 32  \w     91.00 177.00   0.50    1.00    --  113.25  77.00 156.38  172
 33  \w     91.00 177.00   0.50    1.00    --  113.25  77.00   0.00  172
 34  \w     42.00 102.00   0.50    1.00    --  113.25 -77.00 -30.00  120
 35  \w    101.00 177.00   0.50    1.00    --  113.25  45.00-150.00  152
 36  \w     42.00 106.00   0.50    1.00    --  113.25 -94.00-150.00  128
 37  \w    101.00 177.00   0.50    1.00    --  113.25  38.00 -10.92  152
 38  \w     91.00 177.00   0.50    1.00    --  113.25  77.00  30.00  172
 39  \w     42.00 102.00   0.50    1.00    --  113.25 -77.00  90.00  120
 40  \w    101.00 177.00   0.50    1.00    --  113.25  45.00  30.00  152
 41  \w     25.00 120.00   0.50    0.22    --   47.95  77.00 120.00  190
 42  \w     25.00  99.00   0.50    0.22    --   47.95  77.00 -30.00  148
 43  \w     25.00 120.00   0.50    0.22    --   47.95  77.00-120.00  190
;
_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      -0.0200267
_diffrn_orient_matrix_UB_12      0.0984681
_diffrn_orient_matrix_UB_13      -0.1044488
_diffrn_orient_matrix_UB_21      -0.1489116
_diffrn_orient_matrix_UB_22      -0.0123244
_diffrn_orient_matrix_UB_23      0.0110355
_diffrn_orient_matrix_UB_31      0.0013151
_diffrn_orient_matrix_UB_32      0.1190388
_diffrn_orient_matrix_UB_33      0.0876428
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22145
_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         70.234
_diffrn_reflns_theta_min         4.312
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.50923
_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    1.315
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0037(4)
_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   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.3331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0
_reflns_number_gt                2108
_reflns_number_total             2186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03182a2.cif
_cod_data_source_block           21MA144_ER-0187
_cod_original_cell_volume        1148.226(15)
_cod_database_code               7714252
_shelx_estimated_absorpt_t_min   0.9
_shelx_estimated_absorpt_t_max   0.95
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.669
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              43456