#------------------------------------------------------------------------------
#$Date: 2023-03-09 01:54:50 +0200 (Thu, 09 Mar 2023) $
#$Revision: 281754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/25/7712543.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7712543
loop_
_publ_author_name
'Pankov, Roman O.'
'Prima, Darya O.'
'Kostyukovich, Alexander Yu'
'Minyaev, Mikhail E.'
'Ananikov, Valentine P.'
_publ_section_title
;
 Synthesis and a combined experimental/theoretical structural study of a
 comprehensive set of Pd/NHC complexes with o-, m-, and
 p-halogen-substituted aryl groups (X = F, Cl, Br, CF₃).
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d2dt03665g
_journal_year                    2023
_chemical_formula_moiety         'C20 H15 Cl4 N3 Pd'
_chemical_formula_sum            'C20 H15 Cl4 N3 Pd'
_chemical_formula_weight         545.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-06 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.6740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5230(3)
_cell_length_b                   11.9245(3)
_cell_length_c                   14.5709(4)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.88
_cell_measurement_theta_min      2.39
_cell_volume                     2117.66(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (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       'φ and ω shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1122
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            86820
_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         33.216
_diffrn_reflns_theta_min         2.307
_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    1.392
_exptl_absorpt_correction_T_max  0.5659
_exptl_absorpt_correction_T_min  0.5116
_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            colourless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.086
_refine_diff_density_max         1.150
_refine_diff_density_min         -1.569
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         8115
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0461
_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/[σ²(Fo²)+(0.0430P)²+1.3379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5400
_reflns_number_total             8115
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03665g2.cif
_cod_data_source_block           3d
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7712543
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.790
_shelx_estimated_absorpt_t_max   0.890
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.75267(2) 0.77102(2) 0.49048(2) 0.01736(7) Uani 1 1 d . . . . .
Cl1 Cl 0.67521(6) 0.86466(6) 0.33636(5) 0.02280(15) Uani 1 1 d . . . . .
Cl2 Cl 0.81545(6) 0.66850(7) 0.63811(5) 0.02667(17) Uani 1 1 d . . . . .
Cl3 Cl 0.34656(7) 0.77411(9) 0.26820(7) 0.0388(2) Uani 1 1 d . . . . .
Cl4 Cl 0.77212(8) 0.35534(8) 0.51164(7) 0.0358(2) Uani 1 1 d . . . . .
N1 N 0.5378(2) 0.6522(2) 0.42665(18) 0.0190(5) Uani 1 1 d . . . . .
N2 N 0.6515(2) 0.5576(2) 0.39076(18) 0.0205(5) Uani 1 1 d . . . . .
N3 N 0.8795(2) 0.8903(2) 0.55639(19) 0.0222(5) Uani 1 1 d . . . . .
C1 C 0.6400(2) 0.6554(3) 0.4318(2) 0.0187(6) Uani 1 1 d . . . . .
C2 C 0.5553(3) 0.4940(3) 0.3580(2) 0.0235(6) Uani 1 1 d . . . . .
H2 H 0.547(3) 0.424(3) 0.324(3) 0.033(10) Uiso 1 1 d . . . . .
C3 C 0.4846(3) 0.5527(3) 0.3809(2) 0.0228(6) Uani 1 1 d . . . . .
H3 H 0.408(3) 0.539(3) 0.372(2) 0.022(9) Uiso 1 1 d . . . . .
C4 C 0.4931(2) 0.7398(3) 0.4641(2) 0.0213(6) Uani 1 1 d . . . . .
C5 C 0.4062(3) 0.8039(3) 0.3977(3) 0.0267(7) Uani 1 1 d . . . . .
C6 C 0.3665(3) 0.8925(3) 0.4348(3) 0.0390(9) Uani 1 1 d D . . . .
H6 H 0.313(3) 0.934(3) 0.390(3) 0.053(13) Uiso 1 1 d D . . . .
C7 C 0.4144(3) 0.9146(4) 0.5377(4) 0.0440(10) Uani 1 1 d D . . . .
H7 H 0.392(3) 0.971(3) 0.564(3) 0.043(12) Uiso 1 1 d D . . . .
C8 C 0.4985(3) 0.8492(4) 0.6037(3) 0.0392(9) Uani 1 1 d D . . . .
H8 H 0.522(3) 0.869(3) 0.6679(19) 0.037(11) Uiso 1 1 d D . . . .
C9 C 0.5391(3) 0.7618(3) 0.5681(3) 0.0261(7) Uani 1 1 d D . . . .
H9 H 0.590(3) 0.716(3) 0.610(3) 0.037(11) Uiso 1 1 d D . . . .
C10 C 0.7490(2) 0.5267(3) 0.3807(2) 0.0211(6) Uani 1 1 d . . . . .
C11 C 0.8109(3) 0.4345(3) 0.4325(2) 0.0254(6) Uani 1 1 d . . . . .
C12 C 0.9038(3) 0.4047(3) 0.4209(3) 0.0301(7) Uani 1 1 d . . . . .
H12 H 0.943(3) 0.343(3) 0.458(3) 0.026(9) Uiso 1 1 d . . . . .
C13 C 0.9351(3) 0.4681(3) 0.3582(3) 0.0333(8) Uani 1 1 d . . . . .
H13 H 0.997(4) 0.452(4) 0.354(3) 0.056(14) Uiso 1 1 d . . . . .
C14 C 0.8751(3) 0.5603(3) 0.3081(3) 0.0308(8) Uani 1 1 d . . . . .
H14 H 0.891(3) 0.606(3) 0.265(3) 0.037(11) Uiso 1 1 d . . . . .
C15 C 0.7813(3) 0.5907(3) 0.3185(2) 0.0252(6) Uani 1 1 d . . . . .
H15 H 0.742(3) 0.651(3) 0.290(3) 0.024(9) Uiso 1 1 d . . . . .
C16 C 0.8649(3) 0.9995(3) 0.5323(3) 0.0265(7) Uani 1 1 d . . . . .
H16 H 0.795(3) 1.025(3) 0.483(3) 0.032(10) Uiso 1 1 d . . . . .
C17 C 0.9468(3) 1.0793(3) 0.5750(3) 0.0325(8) Uani 1 1 d . . . . .
H17 H 0.927(3) 1.156(3) 0.557(3) 0.029(10) Uiso 1 1 d . . . . .
C18 C 1.0504(3) 1.0448(4) 0.6432(3) 0.0365(9) Uani 1 1 d . . . . .
H18 H 1.110(3) 1.095(3) 0.670(3) 0.040(11) Uiso 1 1 d . . . . .
C19 C 1.0665(3) 0.9336(4) 0.6690(3) 0.0341(8) Uani 1 1 d . . . . .
H19 H 1.137(4) 0.904(3) 0.710(3) 0.047(12) Uiso 1 1 d . . . . .
C20 C 0.9809(3) 0.8586(3) 0.6263(2) 0.0275(7) Uani 1 1 d . . . . .
H20 H 0.988(3) 0.784(3) 0.641(3) 0.033(11) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Pd1 N3 177.50(12) . . ?
C1 Pd1 Cl2 86.32(8) . . ?
N3 Pd1 Cl2 91.98(7) . . ?
C1 Pd1 Cl1 88.67(8) . . ?
N3 Pd1 Cl1 93.06(7) . . ?
Cl2 Pd1 Cl1 174.85(3) . . ?
C1 N1 C3 110.7(2) . . ?
C1 N1 C4 123.4(3) . . ?
C3 N1 C4 125.9(3) . . ?
C1 N2 C2 110.5(2) . . ?
C1 N2 C10 123.6(3) . . ?
C2 N2 C10 125.8(3) . . ?
C16 N3 C20 116.9(3) . . ?
C16 N3 Pd1 122.4(2) . . ?
C20 N3 Pd1 120.7(2) . . ?
N1 C1 N2 105.2(3) . . ?
N1 C1 Pd1 128.9(2) . . ?
N2 C1 Pd1 125.8(2) . . ?
C3 C2 N2 106.9(3) . . ?
C3 C2 H2 131(2) . . ?
N2 C2 H2 122(2) . . ?
C2 C3 N1 106.7(3) . . ?
C2 C3 H3 134(2) . . ?
N1 C3 H3 119.7(19) . . ?
C5 C4 C9 120.1(3) . . ?
C5 C4 N1 120.6(3) . . ?
C9 C4 N1 119.3(3) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 Cl3 120.0(3) . . ?
C6 C5 Cl3 120.0(3) . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 122(3) . . ?
C5 C6 H6 118(3) . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 117(3) . . ?
C6 C7 H7 122(3) . . ?
C7 C8 C9 120.7(4) . . ?
C7 C8 H8 114(3) . . ?
C9 C8 H8 125(3) . . ?
C8 C9 C4 119.2(3) . . ?
C8 C9 H9 122(3) . . ?
C4 C9 H9 119(3) . . ?
C11 C10 C15 120.1(3) . . ?
C11 C10 N2 120.8(3) . . ?
C15 C10 N2 119.2(3) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 Cl4 119.5(3) . . ?
C10 C11 Cl4 120.4(2) . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 H12 117(2) . . ?
C13 C12 H12 124(2) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 120(3) . . ?
C12 C13 H13 120(3) . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 125(2) . . ?
C15 C14 H14 115(2) . . ?
C14 C15 C10 119.2(3) . . ?
C14 C15 H15 124(2) . . ?
C10 C15 H15 117(2) . . ?
N3 C16 C17 123.4(3) . . ?
N3 C16 H16 120(2) . . ?
C17 C16 H16 117(2) . . ?
C18 C17 C16 118.8(4) . . ?
C18 C17 H17 124(2) . . ?
C16 C17 H17 117(2) . . ?
C19 C18 C17 118.4(4) . . ?
C19 C18 H18 120(3) . . ?
C17 C18 H18 122(3) . . ?
C18 C19 C20 120.0(4) . . ?
C18 C19 H19 122(3) . . ?
C20 C19 H19 117(3) . . ?
N3 C20 C19 122.4(4) . . ?
N3 C20 H20 115(3) . . ?
C19 C20 H20 123(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C1 1.956(3) . ?
Pd1 N3 2.112(3) . ?
Pd1 Cl2 2.2935(8) . ?
Pd1 Cl1 2.3128(7) . ?
Cl3 C5 1.738(4) . ?
Cl4 C11 1.738(3) . ?
N1 C1 1.351(4) . ?
N1 C3 1.397(4) . ?
N1 C4 1.429(4) . ?
N2 C1 1.351(4) . ?
N2 C2 1.399(4) . ?
N2 C10 1.436(4) . ?
N3 C16 1.342(4) . ?
N3 C20 1.360(4) . ?
C2 C3 1.339(4) . ?
C2 H2 0.95(4) . ?
C3 H3 1.00(3) . ?
C4 C5 1.384(4) . ?
C4 C9 1.390(4) . ?
C5 C6 1.395(5) . ?
C6 C7 1.377(6) . ?
C6 H6 0.88(2) . ?
C7 C8 1.370(6) . ?
C7 H7 0.89(2) . ?
C8 C9 1.380(5) . ?
C8 H8 0.88(2) . ?
C9 H9 0.88(2) . ?
C10 C11 1.390(4) . ?
C10 C15 1.392(4) . ?
C11 C12 1.384(4) . ?
C12 C13 1.387(5) . ?
C12 H12 0.93(4) . ?
C13 C14 1.374(5) . ?
C13 H13 0.89(5) . ?
C14 C15 1.389(4) . ?
C14 H14 0.93(4) . ?
C15 H15 0.89(4) . ?
C16 C17 1.387(5) . ?
C16 H16 0.95(4) . ?
C17 C18 1.384(6) . ?
C17 H17 0.95(4) . ?
C18 C19 1.370(6) . ?
C18 H18 0.95(4) . ?
C19 C20 1.380(5) . ?
C19 H19 0.95(4) . ?
C20 H20 0.91(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -0.8(3) . . . . ?
C4 N1 C1 N2 178.9(3) . . . . ?
C3 N1 C1 Pd1 -178.4(2) . . . . ?
C4 N1 C1 Pd1 1.3(4) . . . . ?
C2 N2 C1 N1 1.1(3) . . . . ?
C10 N2 C1 N1 179.6(3) . . . . ?
C2 N2 C1 Pd1 178.8(2) . . . . ?
C10 N2 C1 Pd1 -2.7(4) . . . . ?
C1 N2 C2 C3 -1.1(3) . . . . ?
C10 N2 C2 C3 -179.5(3) . . . . ?
N2 C2 C3 N1 0.5(3) . . . . ?
C1 N1 C3 C2 0.2(3) . . . . ?
C4 N1 C3 C2 -179.5(3) . . . . ?
C1 N1 C4 C5 113.1(3) . . . . ?
C3 N1 C4 C5 -67.3(4) . . . . ?
C1 N1 C4 C9 -65.7(4) . . . . ?
C3 N1 C4 C9 113.9(3) . . . . ?
C9 C4 C5 C6 1.7(5) . . . . ?
N1 C4 C5 C6 -177.0(3) . . . . ?
C9 C4 C5 Cl3 -178.4(2) . . . . ?
N1 C4 C5 Cl3 2.8(4) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
Cl3 C5 C6 C7 179.6(3) . . . . ?
C5 C6 C7 C8 -1.3(6) . . . . ?
C6 C7 C8 C9 1.7(6) . . . . ?
C7 C8 C9 C4 -0.5(6) . . . . ?
C5 C4 C9 C8 -1.3(5) . . . . ?
N1 C4 C9 C8 177.5(3) . . . . ?
C1 N2 C10 C11 116.3(3) . . . . ?
C2 N2 C10 C11 -65.4(4) . . . . ?
C1 N2 C10 C15 -63.3(4) . . . . ?
C2 N2 C10 C15 114.9(3) . . . . ?
C15 C10 C11 C12 -1.3(5) . . . . ?
N2 C10 C11 C12 179.0(3) . . . . ?
C15 C10 C11 Cl4 179.1(2) . . . . ?
N2 C10 C11 Cl4 -0.5(4) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
Cl4 C11 C12 C13 -179.7(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?
C11 C10 C15 C14 0.9(5) . . . . ?
N2 C10 C15 C14 -179.5(3) . . . . ?
C20 N3 C16 C17 -0.2(4) . . . . ?
Pd1 N3 C16 C17 179.7(2) . . . . ?
N3 C16 C17 C18 2.5(5) . . . . ?
C16 C17 C18 C19 -2.8(5) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C16 N3 C20 C19 -1.8(4) . . . . ?
Pd1 N3 C20 C19 178.3(2) . . . . ?
C18 C19 C20 N3 1.5(5) . . . . ?
