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_7717249
_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         'C26 H34 Cl2 Pd2, 1[C6H14]'
_chemical_formula_sum            'C32 H48 Cl2 Pd2'
_chemical_formula_weight         716.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 91.464(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0531(2)
_cell_length_b                   13.6424(6)
_cell_length_c                   38.9669(14)
_cell_measurement_reflns_used    5383
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.4630
_cell_measurement_theta_min      3.4100
_cell_volume                     3216.8(2)
_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_environment      N~2~
_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 0.980
_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   -114.00 -13.00   1.00    8.00    --  -41.43 -57.00-150.00  101
  2  \w     27.00  97.00   1.00    8.00    --   41.43-125.00-180.00   70
  3  \w     27.00  97.00   1.00    8.00    --   41.43-125.00  30.00   70
  4  \w     34.00 135.00   1.00   45.00    --  106.01 -61.00   0.00  101
  5  \w    103.00 178.00   1.00   45.00    --  106.01  77.00  30.00   75
  6  \w    103.00 178.00   1.00   45.00    --  106.01  77.00   0.00   75
  7  \w     77.00 178.00   1.00   45.00    --  106.01  61.00 150.00  101
  8  \w     18.00 178.00   1.00   45.00    --  106.01   0.00 -30.00  160
  9  \w     33.00  95.00   1.00   45.00    --  106.01-125.00-180.00   62
 10  \w    -74.00  35.00   1.00    8.00    --  -41.43  77.00 -60.00  109
 11  \w   -114.00 -13.00   1.00    8.00    --  -41.43 -57.00 -30.00  101
 12  \w    -75.00 -13.00   1.00    8.00    --  -41.43 -57.00  90.00   62
 13  \w    103.00 178.00   1.00   45.00    --  106.01  77.00 -30.00   75
 14  \w     33.00  94.00   1.00   45.00    --  106.01-125.00   0.00   61
 15  \w     77.00 178.00   1.00   45.00    --  106.01  61.00  30.00  101
 16  \w     99.00 178.00   1.00   45.00    --  106.01  61.00 -60.00   79
 17  \w    118.00 178.00   1.00   45.00    --  106.01  61.00-150.00   60
 18  \w     77.00 178.00   1.00   45.00    --  106.01  61.00  90.00  101
 19  \w   -114.00 -88.00   1.00    8.00    --  -41.43 -57.00  30.00   26
 20  \w     -7.00  69.00   1.00    8.00    --   41.43 -77.00  90.00   76
;
_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      -0.0020035000
_diffrn_orient_matrix_UB_12      0.0018010000
_diffrn_orient_matrix_UB_13      -0.0395474000
_diffrn_orient_matrix_UB_21      -0.1278550000
_diffrn_orient_matrix_UB_22      -0.0976145000
_diffrn_orient_matrix_UB_23      -0.0007473000
_diffrn_orient_matrix_UB_31      -0.2200828000
_diffrn_orient_matrix_UB_32      0.0567553000
_diffrn_orient_matrix_UB_33      -0.0003907000
_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  0.0568
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            16016
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.972
_diffrn_reflns_theta_min         4.540
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.668
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.847
_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    1.479
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.598
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0792P)^2^+0.1440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2636
_reflns_number_total             3212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02533d2.cif
_cod_data_source_block           fb_178
_cod_depositor_comments
'Adding full bibliography for 7717248--7717252.cif.'
_cod_database_code               7717249
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N2 O2'
_shelx_estimated_absorpt_t_max   0.675
_shelx_estimated_absorpt_t_min   0.250
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C10 = C10-C11 = C10-C13 = C10-C7
 1.54 with sigma of 0.02
 C2-H2
 1 with sigma of 0.01
 C3-H3
 1 with sigma of 0.01
 C1-H1A = C1-H1B
 0.99 with sigma of 0.01
 C12-C11 = C12-C13 = C12-C7 = C11-C13 = C11-C7 = C13-C7
 2.54 with sigma of 0.04
 H3-C4
 2.3 with sigma of 0.01
 Pd1-H3
 2.28 with sigma of 0.04
 C2-H3
 2.12 with sigma of 0.01
 C2-H1A
 2.12 with sigma of 0.01
 C2-H1B
 2.08 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12
\\sim C13: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 206 electrons were 
found in a volume of 886\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[C6H14] per Formula Unit 
which account for 200 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              41713
_shelx_hkl_checksum              28061
_shelx_fab_checksum              86478
_olex2_date_sample_data_collection 2021-12-14
_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 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.689