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_7717250
_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         'C24 H30 Cl2 Pd2'
_chemical_formula_sum            'C24 H30 Cl2 Pd2'
_chemical_formula_weight         602.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-29
_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                99.334(2)
_cell_angle_beta                 96.009(2)
_cell_angle_gamma                90.598(2)
_cell_formula_units_Z            3
_cell_length_a                   5.8033(2)
_cell_length_b                   13.9114(4)
_cell_length_c                   22.1869(6)
_cell_measurement_reflns_used    9670
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.0950
_cell_measurement_theta_min      3.1910
_cell_volume                     1757.08(9)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_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    3.50    --  -41.68 125.00-120.00   81
  2  \w    -70.00  31.00   1.00    3.50    --  -41.68  57.00-180.00  101
  3  \w   -115.00 -14.00   1.00    3.50    --  -41.68 -57.00  30.00  101
  4  \w    -33.00  66.00   1.00    3.50    --   41.68 -38.00-120.00   99
  5  \w     80.00 178.00   1.00   13.00    --  106.01  45.00 120.00   98
  6  \w     78.00 178.00   1.00   13.00    --  106.01  30.00  30.00  100
  7  \w     80.00 178.00   1.00   13.00    --  106.01  45.00  90.00   98
  8  \w     23.00  98.00   1.00   13.00    --  106.01 -94.00 -30.00   75
  9  \w     23.00 107.00   1.00   13.00    --  106.01 -94.00  60.00   84
 10  \w     97.00 178.00   1.00   13.00    --  106.01 125.00  30.00   81
 11  \w     30.00 134.00   1.00   13.00    --  106.01 -30.00  90.00  104
 12  \w     30.00 139.00   1.00   13.00    --  106.01 -77.00 120.00  109
 13  \w     33.00 112.00   1.00   13.00    --  106.01-125.00 -60.00   79
 14  \w     34.00 135.00   1.00   13.00    --  106.01 -61.00 -30.00  101
 15  \w     33.00 112.00   1.00   13.00    --  106.01-125.00-150.00   79
 16  \w   -115.00 -14.00   1.00    3.50    --  -41.68 -57.00 -60.00  101
 17  \w    -66.00  33.00   1.00    3.50    --  -41.68  38.00  90.00   99
 18  \w   -115.00 -14.00   1.00    3.50    --  -41.68 -57.00-150.00  101
 19  \w   -115.00 -14.00   1.00    3.50    --  -41.68 -57.00 120.00  101
 20  \w     14.00 115.00   1.00    3.50    --   41.68  57.00 -60.00  101
 21  \w     80.00 178.00   1.00   13.00    --  106.01  45.00 -30.00   98
 22  \w     77.00 178.00   1.00   13.00    --  106.01  61.00-180.00  101
 23  \w     53.00 178.00   1.00   13.00    --  106.01  15.00 -90.00  125
 24  \w    107.00 178.00   1.00   13.00    --  106.01  61.00-120.00   71
 25  \w     77.00 178.00   1.00   13.00    --  106.01  61.00  30.00  101
 26  \w    128.00 178.00   1.00   13.00    --  106.01  61.00 -90.00   50
 27  \w     77.00 178.00   1.00   13.00    --  106.01  61.00-150.00  101
 28  \w     77.00 178.00   1.00   13.00    --  106.01  61.00  60.00  101
 29  \w     77.00 178.00   1.00   13.00    --  106.01  61.00 -30.00  101
 30  \w     78.00 157.00   1.00   13.00    --  106.01  30.00-180.00   79
;
_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      0.1448534000
_diffrn_orient_matrix_UB_12      0.0945108000
_diffrn_orient_matrix_UB_13      0.0033141000
_diffrn_orient_matrix_UB_21      0.2241227000
_diffrn_orient_matrix_UB_22      -0.0563867000
_diffrn_orient_matrix_UB_23      0.0099789000
_diffrn_orient_matrix_UB_31      0.0096991000
_diffrn_orient_matrix_UB_32      -0.0222040000
_diffrn_orient_matrix_UB_33      -0.0699944000
_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  0.0735
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31485
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.945
_diffrn_reflns_theta_min         3.221
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.522
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_description       needle
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.207
_refine_diff_density_min         -1.200
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6987
_refine_ls_number_restraints     89
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+1.4580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1486
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5192
_reflns_number_total             6987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02533d2.cif
_cod_data_source_block           fb180_dcmhex
_cod_depositor_comments
'Adding full bibliography for 7717248--7717252.cif.'
_cod_database_code               7717250
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H30 Pd2 Cl2'
_shelx_estimated_absorpt_t_max   0.594
_shelx_estimated_absorpt_t_min   0.135
_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
 C27B-C28
 1.49 with sigma of 0.01
 C25B-C26B
 1.42 with sigma of 0.01
 C27B-C26B
 1.42 with sigma of 0.01
 C27A-C28
 1.49 with sigma of 0.01
 C25A-C26A
 1.42 with sigma of 0.01
 C27A-C26A
 1.42 with sigma of 0.02
 C15-C14
 1.42 with sigma of 0.01
 C25B-C27B = C26B-C28
 2.5 with sigma of 0.02
 C25A-C27A = C26A-C28
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C28 \\sim C25B \\sim C26B \\sim C27B \\sim C27A \\sim C25A \\sim C26A: within
2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(C25B)=Sof(H25A)=Sof(H25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=1-FVAR(1)
 Sof(C27A)=Sof(H27A)=Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15), C2(H2), C3(H3), C26B(H26B), C27B(H27B), C27A(H27A),
 C26A(H26A)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C1(H1A,H1B), C25B(H25A,H25B), C25A(H25C,H25D)
5.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C6(H6), C8(H8), C32(H32), C30(H30)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C10(H10A,H10B,
 H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C36(H36A,H36B,H36C), C35(H35A,
 H35B,H35C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              41211
_shelx_hkl_checksum              24893
_olex2_date_sample_data_collection 2022-02-22
_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 1.893
_oxdiff_exptl_absorpt_empirical_full_min 0.685