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

data_7714257
_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         'C12 H11 Cl2 N3 O Pd'
_chemical_formula_sum            'C12 H11 Cl2 N3 O Pd'
_chemical_formula_weight         390.561
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-25 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.8439(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.44149(12)
_cell_length_b                   11.38265(13)
_cell_length_c                   11.56249(13)
_cell_measurement_reflns_used    25623
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      79.9730
_cell_measurement_theta_min      3.7950
_cell_volume                     1374.07(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9997
_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    -97.00 -35.00   0.50    0.15    --  -23.00 170.00 111.00  124
  2  \w    -62.00  -5.00   0.50    0.15    --  -23.00 115.00 -31.00  114
  3  \w     27.00  88.00   0.50    0.15    --   47.92-115.00-121.00  122
  4  \w     45.00 109.00   0.50    0.60    --  113.25-115.00-121.00  128
  5  \w    -96.00 -10.00   0.50    0.15    --  -23.00 -38.00-150.00  172
  6  \w    -94.00 -44.00   0.50    0.15    --  -23.00-170.00  95.00  100
  7  \w    -36.00  50.00   0.50    0.15    --  -23.00  38.00   0.00  172
  8  \w    -28.00  52.00   0.50    0.15    --  -23.00  15.00-180.00  160
  9  \w    -46.00  50.00   0.50    0.15    --  -23.00  77.00  30.00  192
 10  \w    -26.00  23.00   0.50    0.15    --   47.92 -19.00-120.00   98
 11  \w    -26.00  23.00   0.50    0.15    --   47.92 -19.00 -90.00   98
 12  \w     -1.00  80.00   0.50    0.15    --   47.92 -99.00-180.00  162
 13  \w    101.00 177.00   0.50    0.60    --  113.25  45.00  30.00  152
 14  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00  90.00  120
 15  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00  90.00   52
 16  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00  90.00  128
 17  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 -30.00  128
 18  \w     97.00 177.00   0.50    0.60    --  113.25  61.00 120.00  160
 19  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00 150.00  120
 20  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 -90.00  128
 21  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00 -90.00   52
 22  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00-120.00   52
 23  \w    100.00 177.00   0.50    0.60    --  113.25  15.00 -60.00  154
 24  \w    101.00 177.00   0.50    0.60    --  113.25  45.00   0.00  152
 25  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 150.00  128
 26  \w     91.00 177.00   0.50    0.60    --  113.25  77.00  90.00  172
 27  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00 -30.00  120
 28  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00-120.00  120
 29  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00  30.00  128
 30  \w    101.00 177.00   0.50    0.60    --  113.25  45.00-150.00  152
 31  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00  60.00  128
 32  \w     91.00 177.00   0.50    0.60    --  113.25  77.00  60.00  172
 33  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00-150.00  128
 34  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00 -60.00  128
 35  \w    101.00 177.00   0.50    0.60    --  113.25  45.00-180.00  152
 36  \w    101.00 177.00   0.50    0.60    --  113.25  45.00 150.00  152
 37  \w     42.00 102.00   0.50    0.60    --  113.25 -77.00 120.00  120
 38  \w     42.00 106.00   0.50    0.60    --  113.25 -94.00   0.00  128
 39  \w    100.00 177.00   0.50    0.60    --  113.25  15.00   0.00  154
 40  \w     42.00  68.00   0.50    0.60    --  113.25 -61.00-150.00   52
 41  \w    101.00 177.00   0.50    0.60    --  113.25  45.00  90.00  152
 42  \w     97.00 177.00   0.50    0.60    --  113.25  61.00 150.00  160
 43  \w     91.00 177.00   0.50    0.60    --  113.25  77.00-150.00  172
 44  \w     25.00 121.00   0.50    0.15    --   47.92  77.00 -60.00  192
 45  \w     25.00 121.00   0.50    0.15    --   47.92  77.00 120.00  192
 46  \w     25.00 121.00   0.50    0.15    --   47.92  77.00-150.00  192
 47  \w     25.00 121.00   0.50    0.15    --   47.92  77.00  30.00  192
;
_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      -0.0865575000
_diffrn_orient_matrix_UB_12      0.0304313000
_diffrn_orient_matrix_UB_13      0.1024964000
_diffrn_orient_matrix_UB_21      -0.0398465000
_diffrn_orient_matrix_UB_22      -0.1299221000
_diffrn_orient_matrix_UB_23      0.0095295000
_diffrn_orient_matrix_UB_31      0.1126043000
_diffrn_orient_matrix_UB_32      -0.0225799000
_diffrn_orient_matrix_UB_33      0.0846941000
_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  0.0692
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27616
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9997
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.44
_diffrn_reflns_theta_min         5.45
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.435
_exptl_absorpt_correction_T_max  0.504
_exptl_absorpt_correction_T_min  0.110
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.6249
_refine_diff_density_min         -0.8033
_refine_diff_density_rms         0.1188
_refine_ls_d_res_high            0.7930
_refine_ls_d_res_low             8.1111
_refine_ls_extinction_coef       0.00131(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0453
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0453
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+2.5765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -9
_reflns_number_gt                2887
_reflns_number_total             2890
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3dt03182a2.cif
_cod_data_source_block           22MA115_ER-0267
_cod_database_code               7714257
_chemical_oxdiff_formula         'C48  H44  Cl8  N12  O4  Pd4  '
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
;
_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 2.398
_oxdiff_exptl_absorpt_empirical_full_min 0.646