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_7712544
_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         'C22 H15 Cl2 F6 N3 Pd'
_chemical_formula_sum            'C22 H15 Cl2 F6 N3 Pd'
_chemical_formula_weight         612.67
_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                 95.962(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9530(3)
_cell_length_b                   14.9603(5)
_cell_length_c                   22.6625(8)
_cell_measurement_reflns_used    3989
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      35.1060
_cell_measurement_theta_min      3.2290
_cell_volume                     2344.58(15)
_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)'
_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 0.931
_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     -3.00  51.00   0.60   55.00    --   17.96-104.00 -45.00   90
  2  \w     39.00  87.60   0.60   55.00    --   17.96-178.00 120.00   81
  3  \w      4.00  89.20   0.60   55.00    --   17.96  57.00   0.00  142
  4  \w      4.00  89.20   0.60   55.00    --   17.96  57.00 120.00  142
  5  \w     -4.00  89.00   0.60   55.00    --   17.96  77.00 150.00  155
  6  \w     42.00  90.00   0.60   55.00    --   17.96 178.00-120.00   80
  7  \w    -28.00  56.00   0.60   55.00    --  -17.65  19.00  90.00  140
  8  \w    -23.00  28.00   0.60   55.00    --   17.96 -99.00   0.00   85
  9  \w    -23.00  49.00   0.60   55.00    --   17.96 -99.00-150.00  120
;
_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      -0.0196334000
_diffrn_orient_matrix_UB_12      0.0455063000
_diffrn_orient_matrix_UB_13      0.0058093000
_diffrn_orient_matrix_UB_21      -0.0533458000
_diffrn_orient_matrix_UB_22      0.0037128000
_diffrn_orient_matrix_UB_23      -0.0283176000
_diffrn_orient_matrix_UB_31      -0.0853616000
_diffrn_orient_matrix_UB_32      -0.0127895000
_diffrn_orient_matrix_UB_33      0.0124388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9367
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.755
_diffrn_reflns_theta_min         2.723
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.083
_exptl_absorpt_correction_T_max  1.403
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.028
_refine_diff_density_max         1.296
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         9367
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0832P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6894
_reflns_number_total             9367
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9948\% 
around [-0.00 -0.00 1.00] (reciprocal) or [0.32 -0.00 0.95] (direct)
;
_cod_data_source_file            d2dt03665g2.cif
_cod_data_source_block           3l
_cod_database_code               7712544
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     PRO-4CF3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.822
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8997(4)
 0.1003(4)
2. Restrained distances
 C9-F1 \\sim C9-F1A \\sim C9-F1B \\sim C9-F2 \\sim C9-F2A \\sim C9-F2B \\sim
C9-F3 \\sim C9-F3A \\sim C9-F3B
 with sigma of 0.003
 F1-F2 \\sim F2-F3 \\sim F1-F3 \\sim F1A-F2A \\sim F2A-F3A \\sim F1A-F3A \\sim
F1B-F2B \\sim F2B-F3B \\sim F1B-
 F3B
 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(F1) = Uanis(F1A) = Uanis(F1B)
Uanis(F2) = Uanis(F2A) = Uanis(F2B)
Uanis(F3) = Uanis(F3A) = Uanis(F3B)
4. Others
 1*[Sof(F1)+Sof(F2)+Sof(F3)]+1*[Sof(F1A)+Sof(F2A)+Sof(F3A)]+1*[Sof(F1B)+
 Sof(F2B)+Sof(F3B)]=1 with esd of 0.0001
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(2)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(3)
;
_shelx_res_checksum              43291
_shelx_hkl_checksum              94640
_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.644
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2