Nitron-derivative-based palladium carbene complexes: structural characterization, theoretical calculations, and catalytic applications in the Mizoroki–Heck coupling reaction
Lee, Ming-Yi; Liao, Chih-Hsiang; Hung, Hsiu-Yu; Lee, Jhen-Yi; Lee, Hon Man; RSC Advances 13 (2023) 27434–27445; doi:10.1039/D3RA05016E

data_7247389
_publ_section_title
;
 Nitron-derivative-based palladium carbene complexes: structural
 characterization, theoretical calculations, and catalytic applications in
 the Mizoroki--Heck coupling reaction
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              27434
_journal_page_last               27445
_journal_paper_doi               10.1039/D3RA05016E
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C26 H44 N8 O3 Pd'
_chemical_formula_sum            'C26 H44 N8 O3 Pd'
_chemical_formula_weight         623.09
_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_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                79.913(2)
_cell_angle_beta                 77.412(2)
_cell_angle_gamma                75.138(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7070(3)
_cell_length_b                   11.5157(3)
_cell_length_c                   12.8117(3)
_cell_measurement_reflns_used    13086
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.6140
_cell_measurement_theta_min      3.5460
_cell_volume                     1478.16(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.995
_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     21.00  57.00   0.50    0.05    --   56.10-125.00  30.00   72
  2  \w     37.00  62.00   0.50    0.05    --   84.37-111.00  60.00   50
  3  \w     35.00  92.00   0.50    0.05    --   76.52-111.00   0.00  114
  4  \w     34.00  84.00   0.50    0.05    --   76.52 -95.00  60.00  100
  5  \w     38.00  64.00   0.50    0.05    --   84.37-111.00 120.00   52
  6  \w     35.00  60.00   0.50    0.05    --   76.52 -95.00 150.00   50
  7  \w     18.00  58.00   0.50    0.05    --   56.10 -95.00 150.00   80
  8  \w     53.00  92.00   0.50    0.05    --   76.52-111.00 -60.00   78
  9  \w     37.00  63.00   0.50    0.05    --   76.52 -95.00 -90.00   52
 10  \w     41.00  72.00   0.50    0.05    --   76.52 -95.00-150.00   62
 11  \w     49.00  92.00   0.50    0.05    --   76.52-111.00-180.00   86
 12  \w     14.00  40.00   0.50    0.05    --   56.10 -95.00-150.00   52
 13  \w     18.00  57.00   0.50    0.05    --   56.10 -95.00-120.00   78
 14  \w     64.00  90.00   0.50    0.05    --   84.37 -95.00 -30.00   52
 15  \w     17.00  48.00   0.50    0.05    --   56.10 -95.00  30.00   62
 16  \w     39.00  65.00   0.50    0.05    --   76.52 -95.00  90.00   52
 17  \w     50.00  92.00   0.50    0.05    --   84.37 -95.00 120.00   84
 18  \w     64.00  90.00   0.50    0.05    --   84.37 -95.00  90.00   52
 19  \w     15.00  44.00   0.50    0.05    --   56.10 -95.00 120.00   58
 20  \w     67.00  92.00   0.50    0.05    --   84.37 -95.00  60.00   50
 21  \w     64.00  89.00   0.50    0.05    --   84.37 -95.00  30.00   50
 22  \w     45.00  90.00   0.50    0.05    --   84.37 -95.00   0.00   90
 23  \w     44.00  92.00   0.50    0.05    --   84.37 -95.00 -60.00   96
 24  \w     15.00  45.00   0.50    0.05    --   56.10 -95.00 -60.00   60
 25  \w     42.00  92.00   0.50    0.05    --   84.37 -95.00-120.00  100
 26  \w     64.00  89.00   0.50    0.05    --   84.37 -95.00-150.00   50
 27  \w     47.00  92.00   0.50    0.05    --   84.37 -95.00-180.00   90
 28  \w     60.00 125.00   0.50    0.05    --   84.37  15.00-180.00  130
 29  \w     77.00 115.00   0.50    0.05    --   69.13  15.00-150.00   76
 30  \w     37.00  63.00   0.50    0.05    --   69.13  15.00-150.00   52
 31  \w     92.00 121.00   0.50    0.05    --   76.52  15.00 -90.00   58
 32  \w     52.00 127.00   0.50    0.05    --   76.52  15.00   0.00  150
 33  \w     69.00 125.00   0.50    0.05    --   84.37  15.00  60.00  112
 34  \w     84.00 119.00   0.50    0.05    --   69.13  15.00 120.00   70
 35  \w     40.00  81.00   0.50    0.05    --   76.52  15.00 150.00   82
 36  \w     38.00  75.00   0.50    0.05    --   69.13  15.00 120.00   74
 37  \w     57.00 134.00   0.50    0.05    --   84.37  15.00 -60.00  154
 38  \w     40.00  88.00   0.50    0.05    --   76.52  15.00 -90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       ' \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16776
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.563
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.393
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5255
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0417P)^2^+1.4088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5127
_reflns_number_total             5255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra05016e2.cif
_cod_data_source_block           complex2
_cod_original_cell_volume        1478.17(7)
_cod_database_code               7247389
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.564
_shelx_estimated_absorpt_t_max   0.615
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N21(H21), N26(H26)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C),
 C38(H38A,H38B,H38C)
;
_shelxl_version_number           2014-3
_shelx_res_checksum              37659