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_1573139
_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         'C48 H53 Cl2 N3 Pd'
_chemical_formula_sum            'C48 H53 Cl2 N3 Pd'
_chemical_formula_weight         849.23
_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             2024-05-05
_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                100.5540(10)
_cell_angle_beta                 103.9520(10)
_cell_angle_gamma                96.6100(10)
_cell_formula_units_Z            4
_cell_length_a                   12.49350(10)
_cell_length_b                   17.71260(10)
_cell_length_c                   22.0093(2)
_cell_measurement_reflns_used    35464
_cell_measurement_temperature    292.98(10)
_cell_measurement_theta_max      73.2460
_cell_measurement_theta_min      2.5590
_cell_volume                     4581.63(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_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      air
_diffrn_ambient_temperature      292.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_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   -101.00 -38.00   0.50    0.15    --  -99.00  77.00 150.00  126
  2  \w   -104.00 -27.00   0.50    0.15    --  -99.00  77.00  90.00  154
  3  \w   -103.00 -28.00   0.50    0.15    --  -99.00  77.00 -60.00  150
  4  \w    -78.00 -36.00   0.50    0.15    --  -99.00  77.00-150.00   84
  5  \w    -21.00   6.00   0.50    0.13    --  -45.87  19.00-180.00   54
  6  \w     -8.00  30.00   0.50    0.13    --  -45.87  19.00 -90.00   76
  7  \w     57.00  91.00   0.50    0.13    --   45.87 160.00-118.00   68
  8  \w    102.00 128.00   0.50    0.15    --   99.00 160.00-118.00   52
  9  \w    133.00 159.00   0.50    0.15    --   99.00  77.00-120.00   52
 10  \w     75.00 116.00   0.50    0.15    --   99.00  77.00-120.00   82
 11  \w     82.00 172.00   0.50    0.15    --   99.00  61.00 -60.00  180
 12  \w     94.00 127.00   0.50    0.15    --   99.00 117.00  89.00   66
 13  \w     31.00 115.00   0.50    0.13    --   45.87  57.00 120.00  168
 14  \w     90.00 166.00   0.50    0.15    --   99.00  45.00  60.00  152
 15  \w    135.00 174.00   0.50    0.15    --   99.00  30.00  30.00   78
 16  \w    105.00 131.00   0.50    0.15    --   99.00  30.00  30.00   52
 17  \w     34.00  60.00   0.50    0.15    --   99.00 -77.00   0.00   52
 18  \w     66.00  91.00   0.50    0.15    --   99.00 -77.00   0.00   50
 19  \w     31.00  69.00   0.50    0.15    --   99.00 -61.00 -30.00   76
 20  \w     28.00  53.00   0.50    0.15    --   99.00 -45.00-180.00   50
 21  \w     28.00  53.00   0.50    0.15    --   99.00 -45.00-150.00   50
 22  \w     28.00  53.00   0.50    0.15    --   99.00 -45.00-120.00   50
 23  \w     27.00  52.00   0.50    0.15    --   99.00 -45.00   0.00   50
 24  \w    -26.00  15.00   0.50    0.13    --   45.87 -19.00   0.00   82
 25  \w     28.00  53.00   0.50    0.15    --   99.00 -45.00  90.00   50
 26  \w     27.00  52.00   0.50    0.15    --   99.00 -45.00 120.00   50
 27  \w     27.00  52.00   0.50    0.15    --   99.00 -45.00 150.00   50
 28  \w     69.00 104.00   0.50    0.15    --   99.00 -94.00  30.00   70
 29  \w     23.00  52.00   0.50    0.13    --   45.87-117.00   2.00   58
 30  \w     29.00  55.00   0.50    0.15    --   99.00-125.00 -60.00   52
 31  \w     68.00 112.00   0.50    0.13    --   45.87-160.00-149.00   88
 32  \w     95.00 136.00   0.50    0.15    --   99.00-160.00-149.00   82
 33  \w     26.00  69.00   0.50    0.15    --   99.00 -94.00-150.00   86
 34  \w     73.00 112.00   0.50    0.15    --   99.00-125.00 -60.00   78
 35  \w     41.00 109.00   0.50    0.15    --   99.00-117.00   2.00  136
 36  \w     32.00  58.00   0.50    0.15    --   99.00 -94.00  30.00   52
 37  \w     82.00 107.00   0.50    0.15    --   99.00-106.00 142.58   50
 38  \w    -98.00 -73.00   0.50    0.13    --  -45.87 160.00-118.00   50
 39  \w    -86.00  -9.00   0.50    0.13    --  -45.87 117.00  89.00  154
 40  \w    -75.00 -50.00   0.50    0.15    --  -99.00 117.00  89.00   50
 41  \w   -135.00 -31.00   0.50    0.15    --  -99.00 160.00-118.00  208
 42  \w    -54.00 -29.00   0.50    0.15    --  -99.00 125.00-150.00   50
 43  \w   -112.00 -30.00   0.50    0.15    --  -99.00 125.00-180.00  164
 44  \w   -172.00-106.00   0.50    0.15    --  -99.00 -94.00 -30.00  132
 45  \w   -168.00-134.00   0.50    0.15    --  -99.00-125.00  60.00   68
 46  \w   -109.00 -81.00   0.50    0.15    --  -99.00-125.00  60.00   56
 47  \w   -146.00-105.00   0.50    0.15    --  -99.00-117.00   2.00   82
 48  \w   -155.00-129.00   0.50    0.15    --  -99.00-160.00-149.00   52
 49  \w    -82.00 -51.00   0.50    0.13    --  -45.87-160.00-149.00   62
 50  \w   -175.00 -95.00   0.50    0.15    --  -99.00 -15.00   0.00  160
 51  \w    -99.00 -22.00   0.50    0.13    --  -45.87 -77.00   0.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0253868000
_diffrn_orient_matrix_UB_12      -0.0772243000
_diffrn_orient_matrix_UB_13      -0.0503028000
_diffrn_orient_matrix_UB_21      0.0007430000
_diffrn_orient_matrix_UB_22      0.0456940000
_diffrn_orient_matrix_UB_23      -0.0531401000
_diffrn_orient_matrix_UB_31      0.1263387000
_diffrn_orient_matrix_UB_32      -0.0005060000
_diffrn_orient_matrix_UB_33      0.0104475000
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            70868
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.543
_diffrn_reflns_theta_min         2.574
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.269
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     993
_refine_ls_number_reflns         17881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+1.8152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14487
_reflns_number_total             17881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4py01026d2.cif
_cod_data_source_block           pd0505
_cod_depositor_comments
'Adding full bibliography for 1573139--1573141.cif.'
_cod_database_code               1573139
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Pd Cl'
_shelx_estimated_absorpt_t_max   0.632
_shelx_estimated_absorpt_t_min   0.546
_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:
 C9(H9), C18(H18), C22(H22), C29(H29), C42(H42), C46(H46), C55(H55), C63(H63),
 C67(H67), C73(H73), C77(H77), C86(H86)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C12(H12), C13(H13), C14(H14), C24(H24), C25(H25),
 C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34), C38(H38), C39(H39),
  C40(H40), C50(H50), C51(H51), C52(H52), C53(H53), C56(H56), C57(H57),
 C58(H58), C59(H59), C69(H69), C70(H70), C71(H71), C82(H82), C83(H83), C84(H84),
  C88(H88), C91(H91), C94(H94)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C),
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C43(H43A,H43B,H43C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C66(H66A,H66B,H66C), C68(H68A,
 H68B,H68C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C),
 C78(H78A,H78B,H78C), C85(H85A,H85B,H85C), C87(H87A,H87B,H87C), C90(H90A,H90B,
 H90C), C93(H93A,H93B,H93C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85514
_shelx_hkl_checksum              75248
_shelx_fab_checksum              69840
_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 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.813