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

data_7714253
_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 Cl2 N3 O Pd'
_chemical_formula_sum            'C13 H13 Cl2 N3 O Pd'
_chemical_formula_weight         404.56
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.80951(16)
_cell_length_b                   14.64287(17)
_cell_length_c                   20.4888(2)
_cell_measurement_reflns_used    15953
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      79.359
_cell_measurement_theta_min      4.884
_cell_volume                     4143.06(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -94.00 -10.00   0.50    0.50    --  -23.00 -49.00 120.00  168
  2  \w    -36.00  50.00   0.50    0.50    --  -23.00  49.00 -92.00  172
  3  \w     35.00 120.00   0.50    0.50    --   47.70  49.00 -92.00  170
  4  \w    -24.00  52.00   0.50    0.50    --   47.70 -49.00 120.00  152
  5  \w    100.00 177.00   0.50    1.80    --  113.25  49.00 -92.00  154
  6  \w     42.00  68.00   0.50    1.80    --  113.25 -61.00 120.00   52
  7  \w     42.00 102.00   0.50    1.80    --  113.25 -77.00   0.00  120
  8  \w     42.00 106.00   0.50    1.80    --  113.25 -94.00 -60.00  128
  9  \w    101.00 177.00   0.50    1.80    --  113.25  30.00   0.00  152
 10  \w     97.00 177.00   0.50    1.80    --  113.25  61.00-180.00  160
 11  \w     25.00 120.00   0.50    0.50    --   47.70  77.00  60.00  190
 12  \w    -24.00  70.00   0.50    0.50    --   47.70 -77.00 -60.00  188
 13  \w     33.00 120.00   0.50    0.50    --   47.70  57.00   0.00  174
 14  \w     25.00 120.00   0.50    0.50    --   47.70  77.00 150.00  190
 15  \w    100.00 177.00   0.50    1.80    --  113.25  15.00 120.00  154
 16  \w     91.00 177.00   0.50    1.80    --  113.25  77.00  30.00  172
 17  \w     42.00  68.00   0.50    1.80    --  113.25 -61.00-180.00   52
 18  \w     42.00 100.00   0.50    1.80    --  113.25 -94.00 120.00  116
;
_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      0.0019842
_diffrn_orient_matrix_UB_12      -0.0852187
_diffrn_orient_matrix_UB_13      0.0440636
_diffrn_orient_matrix_UB_21      0.1093221
_diffrn_orient_matrix_UB_22      0.0136015
_diffrn_orient_matrix_UB_23      0.0111378
_diffrn_orient_matrix_UB_31      -0.0217938
_diffrn_orient_matrix_UB_32      0.0601897
_diffrn_orient_matrix_UB_33      0.0599516
_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  0.0572
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30476
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.076
_diffrn_reflns_theta_min         4.903
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.593
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.29594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.059
_refine_diff_density_max         1.334
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0804P)^2^+2.0787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.125
_reflns_Friedel_coverage         0
_reflns_number_gt                3309
_reflns_number_total             3774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03182a2.cif
_cod_data_source_block           21MA078_ER-0186
_cod_database_code               7714253
_shelx_estimated_absorpt_t_min   0.194
_shelx_estimated_absorpt_t_max   0.601
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.712
_oxdiff_exptl_absorpt_empirical_full_min 0.535
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
        1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
        2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C11(H11), C2(H2), C9(H9), C10(H10), C3(H3)
        2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              51598
_shelx_fab_checksum              61993