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_7712542
_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_formula_moiety         'C20 H15 Br2 Cl2 N3 Pd'
_chemical_formula_sum            'C20 H15 Br2 Cl2 N3 Pd'
_chemical_formula_weight         634.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-10-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-10-07 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.197(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.96427(16)
_cell_length_b                   14.9658(3)
_cell_length_c                   21.8956(5)
_cell_measurement_reflns_used    8527
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      35.6370
_cell_measurement_theta_min      2.7270
_cell_volume                     2258.77(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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      4.00  90.00   0.50   62.00    --   17.96  58.00   4.00  172
  2  \w    -54.00  32.00   0.50   62.00    --   17.96 -58.00-136.00  172
  3  \w    -56.00   5.00   0.50   62.00    --   17.96 -19.00  90.00  122
  4  \w     42.00  90.00   0.50   62.00    --   17.96 178.00-120.00   96
  5  \w     42.00  90.00   0.50   62.00    --   17.96 178.00 -30.00   96
  6  \w     42.00  90.00   0.50   62.00    --   17.96 178.00-150.00   96
  7  \w    -90.00   4.00   0.50   62.00    --  -17.65 -77.00-180.00  188
  8  \w    -56.00   5.00   0.50   62.00    --   17.96 -19.00 -90.00  122
  9  \w    -23.00  20.00   0.50   62.00    --   17.96 -99.00  60.00   86
 10  \w     39.00  89.00   0.50   62.00    --   17.96-178.00  90.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0511730000
_diffrn_orient_matrix_UB_12      -0.0132090000
_diffrn_orient_matrix_UB_13      0.0242920000
_diffrn_orient_matrix_UB_21      0.0566068000
_diffrn_orient_matrix_UB_22      0.0298919000
_diffrn_orient_matrix_UB_23      0.0203001000
_diffrn_orient_matrix_UB_31      -0.0690258000
_diffrn_orient_matrix_UB_32      0.0343213000
_diffrn_orient_matrix_UB_33      -0.0083226000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            26930
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.997
_diffrn_reflns_theta_min         2.722
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.051
_refine_diff_density_max         1.170
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         4576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+1.3650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3895
_reflns_number_total             4576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03665g2.cif
_cod_data_source_block           3i
_cod_database_code               7712542
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H15Br2Cl2N3Pd
_chemical_oxdiff_usercomment     PRO-4Br
_shelx_estimated_absorpt_t_max   0.799
_shelx_estimated_absorpt_t_min   0.508
_olex2_refinement_description
;
;
_shelx_res_checksum              93152
_shelx_hkl_checksum              88097
_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 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.777