Synthesis and a combined experimental/theoretical structural study of a comprehensive set of Pd/NHC complexes with <i>o</i>-, <i>m</i>-, and <i>p</i>-halogen-substituted aryl groups (X = F, Cl, Br, CF<sub>3</sub>).
Pankov, Roman O.; Prima, Darya O.; Kostyukovich, Alexander Yu; Minyaev, Mikhail E.; Ananikov, Valentine P.; Dalton transactions (Cambridge, England : 2003)  (2023) –; doi:10.1039/d2dt03665g

data_7712541
_publ_section_title
;
 Synthesis and a combined experimental/theoretical structural study of a
 comprehensive set of Pd/NHC complexes with <i>o</i>-, <i>m</i>-, and
 <i>p</i>-halogen-substituted aryl groups (X = F, Cl, Br, CF<sub>3</sub>).
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d2dt03665g
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H15 Cl2 F6 N3 Pd'
_chemical_formula_sum            'C22 H15 Cl2 F6 N3 Pd'
_chemical_formula_weight         612.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-10-07 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.2866(7)
_cell_length_b                   8.7886(2)
_cell_length_c                   14.5007(3)
_cell_measurement_reflns_used    9636
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.74
_cell_measurement_theta_min      2.77
_cell_volume                     4624.40(17)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_structure_refinement
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_structure_solution
'SHELXT (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49547
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.595
_diffrn_reflns_theta_min         2.245
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1957 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(6)
_refine_ls_extinction_coef       0.00020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0143
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0163P)^2^+5.6460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0350
_refine_ls_wR_factor_ref         0.0355
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4142
_reflns_number_total             4224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03665g2.cif
_cod_data_source_block           3k
_cod_database_code               7712541
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.625
_shelx_estimated_absorpt_t_max   0.883
_shelx_res_checksum              89488
_shelx_hkl_checksum              57489