Dibenzobarrelene-derived Pd-NHCs: efficient precatalysts for the Suzuki–Miyaura polycondensations of dichloroarene monomers
Guo, Yuman; Wu, Hao; Zhang, Meng-Jiao; Liu, Feng-Shou; Polymer Chemistry 15 (2024) 4962–4971; doi:10.1039/D4PY01026D

data_1573141
_publ_section_title
;
 Dibenzobarrelene-derived Pd-NHCs: efficient precatalysts for the
 Suzuki--Miyaura polycondensations of dichloroarene monomers
;
_journal_issue                   48
_journal_name_full               'Polymer Chemistry'
_journal_page_first              4962
_journal_page_last               4971
_journal_paper_doi               10.1039/D4PY01026D
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C82 H88 Cl4 N4 Pd2'
_chemical_formula_sum            'C82 H88 Cl4 N4 Pd2'
_chemical_formula_weight         1484.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-09-10 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.068(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9002(4)
_cell_length_b                   27.2207(10)
_cell_length_c                   20.8068(7)
_cell_measurement_reflns_used    7572
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.3270
_cell_measurement_theta_min      2.6160
_cell_volume                     7306.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (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      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.959
_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    -65.00  24.00   1.00    4.00    --  -40.73  38.00 150.00   89
  2  \w    -40.00  -6.00   1.00    4.00    --  -40.73 125.00 -30.00   34
  3  \w     81.00 173.00   1.00    6.00    --  107.58  77.00 -90.00   92
  4  \w     82.00 163.00   1.00    6.00    --  107.58  45.00  60.00   81
  5  \w    111.00 167.00   1.00    6.00    --  107.58 125.00  90.00   56
  6  \w     71.00 126.00   1.00    6.00    --  107.58 -61.00   0.00   55
  7  \w     24.00  87.00   1.00    4.00    --   40.73-125.00 -90.00   63
  8  \w    -52.00  -6.00   1.00    4.00    --  -41.23  38.00  30.00   46
  9  \w     87.00 113.00   1.00    4.00    --   41.23  38.00-120.00   26
 10  \w     37.00  84.00   1.00    6.00    --  107.58 -61.00-120.00   47
 11  \w     33.00  58.00   1.00    6.00    --  107.58 -94.00 120.00   25
 12  \w     60.00 103.00   1.00    4.00    --  107.58 -94.00 120.00   43
 13  \w     87.00 113.00   1.00    4.00    --  107.58  77.00   0.00   26
 14  \w    132.00 171.00   1.00    4.00    --  107.58  77.00   0.00   39
 15  \w     96.00 133.00   1.00    4.00    --  107.58 -61.00-120.00   37
 16  \w    127.00 153.00   1.00    4.00    --  107.58 105.00 -81.00   26
 17  \w     70.00  96.00   1.00    4.00    --  107.58 -94.00  60.00   26
 18  \w    -77.00 -51.00   1.00    2.00    --  -40.98 125.00 -60.00   26
 19  \w   -108.00 -47.00   1.00    2.00    --  -40.98 -38.00-180.00   61
 20  \w     89.00 158.00   1.00    4.00    --  107.58  45.00-180.00   69
 21  \w    139.00 176.00   1.00    4.00    --  107.58 125.00 -30.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0843906000
_diffrn_orient_matrix_UB_12      0.0362301000
_diffrn_orient_matrix_UB_13      -0.0223022000
_diffrn_orient_matrix_UB_21      0.0509372000
_diffrn_orient_matrix_UB_22      0.0409937000
_diffrn_orient_matrix_UB_23      0.0401962000
_diffrn_orient_matrix_UB_31      0.0673686000
_diffrn_orient_matrix_UB_32      0.0145161000
_diffrn_orient_matrix_UB_33      -0.0580625000
_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  0.1102
_diffrn_reflns_av_unetI/netI     0.1261
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            42105
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.868
_diffrn_reflns_theta_min         2.673
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             3072
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.924
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     845
_refine_ls_number_reflns         14193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0699
_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^)+(0.0674P)^2^+0.6780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9376
_reflns_number_total             14193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4py01026d2.cif
_cod_data_source_block           m500
_cod_depositor_comments
'Adding full bibliography for 1573139--1573141.cif.'
_cod_database_code               1573141
_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 Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C24(H24), C28(H28), C33(H33), C40(H40), C46(H46), C53(H53),
 C58(H58), C65(H65), C73(H73), C81(H81)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C21(H21), C22(H22), C37(H37), C38(H38), C39(H39), C48(H48), C49(H49),
  C50(H50), C60(H60), C61(H61), C62(H62), C63(H63), C68(H68), C69(H69),
 C70(H70), C71(H71), C76(H76), C77(H77), C78(H78)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C52(H52A,H52B,H52C),
 C54(H54A,H54B,H54C), C72(H72A,H72B,H72C), C74(H74A,H74B,H74C), C82(H82A,H82B,
 H82C), C83(H83A,H83B,H83C)
;
_shelx_res_checksum              88519
_shelx_hkl_checksum              74429
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.367
_oxdiff_exptl_absorpt_empirical_full_min 0.572