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_1573140
_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         'C44 H48 Cl2 N4 Pd S, C H2 Cl2'
_chemical_formula_sum            'C45 H50 Cl4 N4 Pd S'
_chemical_formula_weight         927.15
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-25
_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                 101.1780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0079(2)
_cell_length_b                   24.0698(3)
_cell_length_c                   13.9399(2)
_cell_measurement_reflns_used    17891
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      3.6210
_cell_volume                     4281.75(11)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     31.00  72.00   1.00    1.09    --   40.73-125.00 -30.00   41
  2  \w     29.00  55.00   1.00    1.09    --   40.73-125.00-120.00   26
  3  \w     24.00  77.00   1.00    1.50    --  106.95 -94.00 -90.00   53
  4  \w     41.00 125.00   1.00    1.50    --  106.95 -45.00 -90.00   84
  5  \w     93.00 176.00   1.00    1.50    --  106.95  30.00  30.00   83
  6  \w    108.00 162.00   1.00    1.50    --  106.95 125.00 -60.00   54
  7  \w     59.00 160.00   1.00    1.50    --  106.95 -15.00   0.00  101
  8  \w     32.00  62.00   1.00    1.50    --  106.95 -94.00 120.00   30
  9  \w     30.00  56.00   1.00    1.50    --  106.95 -15.00   0.00   26
 10  \w     25.00  52.00   1.00    2.00    --   40.73-125.00  30.00   27
 11  \w   -116.00  40.00   1.00    2.00    --  -40.73   0.00 -60.00  156
 12  \w    108.00 133.00   1.00    5.00    --  106.95 -45.00 150.00   25
 13  \w     -4.00  38.00   1.00    2.00    --  -40.98  19.00 -30.00   42
 14  \w   -114.00 -40.00   1.00    2.00    --  -40.98 -38.00 150.00   74
 15  \w      1.00  41.00   1.00    2.00    --   40.98 -99.00  30.00   40
 16  \w     79.00 158.00   1.00    5.00    --  106.95  61.00 150.00   79
 17  \w     76.00 102.00   1.00    5.00    --  106.95  77.00 120.00   26
 18  \w     78.00 104.00   1.00    5.00    --  106.95  61.00 120.00   26
 19  \w    105.00 177.00   1.00    5.00    --  106.95  45.00  90.00   72
 20  \w    137.00 163.00   1.00    5.00    --  106.95 125.00 150.00   26
 21  \w     37.00  63.00   1.00    5.00    --  106.95-125.00 -60.00   26
 22  \w     88.00 117.00   1.00    5.00    --  106.95-125.00 -60.00   29
 23  \w     80.00 163.00   1.00    5.00    --  106.95  30.00-150.00   83
 24  \w    105.00 145.00   1.00    5.00    --  106.95  77.00 120.00   40
 25  \w     63.00 104.00   1.00    5.00    --  106.95 -94.00 -30.00   41
 26  \w     43.00  77.00   1.00    5.00    --  106.95 -94.00 -60.00   34
;
_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      0.0625481000
_diffrn_orient_matrix_UB_12      0.0445343000
_diffrn_orient_matrix_UB_13      0.0664621000
_diffrn_orient_matrix_UB_21      -0.0485551000
_diffrn_orient_matrix_UB_22      -0.0203381000
_diffrn_orient_matrix_UB_23      0.0862130000
_diffrn_orient_matrix_UB_31      0.0910618000
_diffrn_orient_matrix_UB_32      -0.0412227000
_diffrn_orient_matrix_UB_33      0.0290671000
_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  0.0571
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.578
_diffrn_reflns_theta_max         66.578
_diffrn_reflns_theta_min         3.673
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69612
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.961
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         7580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0622P)^2^+11.0575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6994
_reflns_number_total             7580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4py01026d2.cif
_cod_data_source_block           exp_5400
_cod_depositor_comments
'Adding full bibliography for 1573139--1573141.cif.'
_cod_database_code               1573140
_shelx_shelxl_version_number     2018/3
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C13(H13), C20(H20), C33(H33), C37(H37), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C23(H23),
 C24(H24), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C42(H42), C43(H43)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C41(H41A,H41B,
 H41C)
;
_shelx_res_checksum              41693
_shelx_hkl_checksum              42195
_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.701