The role of the stabilizing/leaving group in palladium catalysed cross-coupling reactions.
Palio, Lorenzo; Bru, Francis; Ruggiero, Tommaso; Bourda, Laurens; Van Hecke, Kristof; Cazin, Catherine; Nolan, Steven P.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 18013–18020; doi:10.1039/d4dt02533d

data_7717248
_publ_section_title
;
 The role of the stabilizing/leaving group in palladium catalysed
 cross-coupling reactions.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              18013
_journal_page_last               18020
_journal_paper_doi               10.1039/d4dt02533d
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C20 H22 Cl2 Pd2'
_chemical_formula_sum            'C20 H22 Cl2 Pd2'
_chemical_formula_weight         546.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.607(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0880(7)
_cell_length_b                   7.4392(9)
_cell_length_c                   15.9356(17)
_cell_measurement_reflns_used    3232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.2340
_cell_measurement_theta_min      5.5070
_cell_volume                     958.76(18)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_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    -87.00  -6.00   1.00    1.00    --  -41.18 125.00-180.00   81
  2  \w   -113.00 -66.00   1.00    1.00    --  -41.18-141.00-106.00   47
  3  \w    -21.00  74.00   1.00    1.00    --   41.18 -77.00  60.00   95
  4  \w     30.00 134.00   1.00    2.50    --  106.01 -30.00 -30.00  104
  5  \w     33.00 112.00   1.00    2.50    --  106.01-125.00-180.00   79
  6  \w     33.00 112.00   1.00    2.50    --  106.01-125.00-120.00   79
  7  \w     23.00 107.00   1.00    2.50    --  106.01 -94.00 -60.00   84
  8  \w   -113.00 -13.00   1.00    1.00    --  -41.18 -57.00   0.00  100
  9  \w   -113.00 -13.00   1.00    1.00    --  -41.18 -57.00 120.00  100
 10  \w     53.00 178.00   1.00    2.50    --  106.01  15.00  60.00  125
 11  \w     53.00 178.00   1.00    2.50    --  106.01  15.00 -60.00  125
 12  \w     77.00 178.00   1.00    2.50    --  106.01  61.00-180.00  101
 13  \w     77.00 178.00   1.00    2.50    --  106.01  61.00 120.00  101
 14  \w   -113.00 -13.00   1.00    1.00    --  -41.18 -57.00-120.00  100
 15  \w   -113.00 -13.00   1.00    1.00    --  -41.18 -57.00 -60.00  100
 16  \w     33.00 132.00   1.00    2.50    --  106.01 -45.00 120.00   99
 17  \w     80.00 153.00   1.00    2.50    --  106.01  45.00  90.00   73
 18  \w     23.00 107.00   1.00    2.50    --  106.01 -94.00  30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0411484000
_diffrn_orient_matrix_UB_12      -0.1743892000
_diffrn_orient_matrix_UB_13      -0.0481504000
_diffrn_orient_matrix_UB_21      0.1857736000
_diffrn_orient_matrix_UB_22      -0.0419326000
_diffrn_orient_matrix_UB_23      -0.0053911000
_diffrn_orient_matrix_UB_31      -0.0097414000
_diffrn_orient_matrix_UB_32      -0.1038800000
_diffrn_orient_matrix_UB_33      0.0835457000
_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  0.0634
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4826
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.851
_diffrn_reflns_theta_min         2.773
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    17.667
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_description       irregular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         3.056
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1031
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0969P)^2^+5.0864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                942
_reflns_number_total             1031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02533d2.cif
_cod_data_source_block           fb181_dcmhex
_cod_depositor_comments
'Adding full bibliography for 7717248--7717252.cif.'
_cod_database_code               7717248
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H22 Cl2 Pd2'
_shelx_estimated_absorpt_t_max   0.472
_shelx_estimated_absorpt_t_min   0.226
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-C4
 1.49 with sigma of 0.005
 C2-C3 = C1-C2
 1.41 with sigma of 0.005
 C1-H1B = C1-H1A
 0.95 with sigma of 0.01
 C2-H2
 0.95 with sigma of 0.01
 C3-H3 = C3-H3_$1
 0.95 with sigma of 0.02
 C1-C3
 2.39 with sigma of 0.01
 C2-C4
 2.57 with sigma of 0.01
 C2-H1A
 1.988 with sigma of 0.01
 H1B-Pd1
 2.608 with sigma of 0.01
 Pd1-H1A
 2.756 with sigma of 0.01
 C2-H1B
 2.216 with sigma of 0.01
 H2-C3
 2.17 with sigma of 0.01
 H2-C1
 2.06 with sigma of 0.01
 Pd1-H2
 2.8 with sigma of 0.01
 C2-H3
 2 with sigma of 0.04
 H3-Pd1
 2.6 with sigma of 0.04
 H3-C4
 2.1 with sigma of 0.04
 C2_$1-H3_$1
 2 with sigma of 0.04
 H3_$1-Pd1
 2.6 with sigma of 0.04
 H3_$1-C4
 2.1 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
4. Others
 Fixed Sof: Cl1(0.5) C1(0.5) C2(0.5) H1A(0.5) H1B(0.5) H2(0.5) H3(0.5)
 H8A(0.5) H8B(0.5) H8C(0.5)
 Fixed Uiso: H2(1.2)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
5.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              9598
_shelx_hkl_checksum              52160
_olex2_date_sample_data_collection 2022-03-04
_olex2_exptl_crystal_mounting_method 'Mounted on a LythoLoop'
_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 2.149
_oxdiff_exptl_absorpt_empirical_full_min 0.600