#------------------------------------------------------------------------------
#$Date: 2023-03-09 01:54:50 +0200 (Thu, 09 Mar 2023) $
#$Revision: 281754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/25/7712538.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_7712538
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           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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
;
2022-10-07 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0789(6)
_cell_length_b                   14.4880(10)
_cell_length_c                   16.3561(12)
_cell_measurement_reflns_used    9237
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.64
_cell_measurement_theta_min      2.56
_cell_volume                     2096.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       'APEX3 (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 0.997
_diffrn_measured_fraction_theta_max 0.998
_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_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4887
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.664
_diffrn_reflns_theta_min         2.698
_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    1.406
_exptl_absorpt_correction_T_max  0.437617
_exptl_absorpt_correction_T_min  0.337528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Twinabs (Bruker, 2019)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00106(15)
_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   1.113
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         4887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0222
_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)+(0.0211P)²+2.2251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4654
_reflns_number_total             4887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03665g2.cif
_cod_data_source_block           3e
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7712538
_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   0.631
_shelx_estimated_absorpt_t_max   0.753
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.500000 0.46889(2) 0.250000 0.01344(3) Uani 1 2 d S T P . .
Cl1 Cl 0.26573(3) 0.46701(2) 0.28172(2) 0.02471(6) Uani 1 1 d . . . . .
Cl2 Cl 1.08059(4) 0.71978(3) 0.51831(2) 0.03412(8) Uani 1 1 d . . . . .
N1 N 0.57960(10) 0.66220(6) 0.30959(6) 0.01500(14) Uani 1 1 d . . . . .
N2 N 0.500000 0.32669(9) 0.250000 0.0151(2) Uani 1 2 d S T P . .
C1 C 0.500000 0.60448(10) 0.250000 0.0128(2) Uani 1 2 d S T P . .
C2 C 0.55030(13) 0.75426(7) 0.28718(7) 0.01758(18) Uani 1 1 d . . . . .
H2 H 0.596(2) 0.8028(12) 0.3193(11) 0.020(4) Uiso 1 1 d . . . . .
C3 C 0.68254(12) 0.63411(8) 0.38514(7) 0.01673(17) Uani 1 1 d . . . . .
C4 C 0.81476(13) 0.68466(9) 0.41168(7) 0.01954(19) Uani 1 1 d . . . . .
H4 H 0.836(2) 0.7356(13) 0.3810(12) 0.024(4) Uiso 1 1 d . . . . .
C5 C 0.91476(13) 0.65731(10) 0.48515(7) 0.0225(2) Uani 1 1 d . . . . .
C6 C 0.88699(15) 0.58167(10) 0.53144(8) 0.0261(2) Uani 1 1 d . . . . .
H6 H 0.968(2) 0.5628(14) 0.5839(13) 0.031(5) Uiso 1 1 d . . . . .
C7 C 0.75260(17) 0.53315(10) 0.50368(8) 0.0266(2) Uani 1 1 d . . . . .
H7 H 0.733(3) 0.4838(15) 0.5374(15) 0.037(6) Uiso 1 1 d . . . . .
C8 C 0.64908(14) 0.55915(9) 0.43111(7) 0.0217(2) Uani 1 1 d . . . . .
H8 H 0.558(2) 0.5269(13) 0.4147(14) 0.031(5) Uiso 1 1 d . . . . .
C9 C 0.61832(12) 0.27938(8) 0.29535(7) 0.01696(17) Uani 1 1 d . . . . .
H9 H 0.700(2) 0.3175(12) 0.3247(11) 0.020(4) Uiso 1 1 d . . . . .
C10 C 0.62182(13) 0.18411(8) 0.29706(8) 0.01902(18) Uani 1 1 d . . . . .
H10 H 0.703(2) 0.1539(14) 0.3275(13) 0.031(5) Uiso 1 1 d . . . . .
C11 C 0.500000 0.13527(11) 0.250000 0.0202(3) Uani 1 2 d S T P . .
H11 H 0.500000 0.071(2) 0.250000 0.027(6) Uiso 1 2 d S . P . .
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 N2 180.0 . . ?
C1 Pd1 Cl1 90.678(7) . . ?
N2 Pd1 Cl1 89.322(7) . . ?
C1 Pd1 Cl1 90.677(7) . 2_655 ?
N2 Pd1 Cl1 89.323(7) . 2_655 ?
Cl1 Pd1 Cl1 178.645(15) . 2_655 ?
C1 N1 C2 111.14(9) . . ?
C1 N1 C3 125.57(9) . . ?
C2 N1 C3 123.28(9) . . ?
C9 N2 C9 118.83(13) 2_655 . ?
C9 N2 Pd1 120.59(7) 2_655 . ?
C9 N2 Pd1 120.58(7) . . ?
N1 C1 N1 104.22(12) 2_655 . ?
N1 C1 Pd1 127.89(6) 2_655 . ?
N1 C1 Pd1 127.89(6) . . ?
C2 C2 N1 106.75(6) 2_655 . ?
C2 C2 H2 130.1(11) 2_655 . ?
N1 C2 H2 123.1(11) . . ?
C4 C3 C8 121.36(10) . . ?
C4 C3 N1 118.05(10) . . ?
C8 C3 N1 120.58(10) . . ?
C3 C4 C5 118.02(11) . . ?
C3 C4 H4 121.2(12) . . ?
C5 C4 H4 120.8(12) . . ?
C6 C5 C4 122.23(11) . . ?
C6 C5 Cl2 119.54(9) . . ?
C4 C5 Cl2 118.23(10) . . ?
C5 C6 C7 118.33(11) . . ?
C5 C6 H6 118.8(12) . . ?
C7 C6 H6 122.9(12) . . ?
C8 C7 C6 121.06(13) . . ?
C8 C7 H7 121.4(14) . . ?
C6 C7 H7 117.5(14) . . ?
C7 C8 C3 118.99(12) . . ?
C7 C8 H8 119.6(13) . . ?
C3 C8 H8 121.4(13) . . ?
N2 C9 C10 122.11(10) . . ?
N2 C9 H9 114.3(11) . . ?
C10 C9 H9 123.6(11) . . ?
C9 C10 C11 119.07(11) . . ?
C9 C10 H10 120.4(13) . . ?
C11 C10 H10 120.5(13) . . ?
C10 C11 C10 118.80(15) . 2_655 ?
C10 C11 H11 120.60(7) . . ?
C10 C11 H11 120.60(7) 2_655 . ?
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 1.9645(14) . ?
Pd1 N2 2.0601(13) . ?
Pd1 Cl1 2.3002(3) . ?
Pd1 Cl1 2.3002(3) 2_655 ?
Cl2 C5 1.7355(13) . ?
N1 C1 1.3616(12) . ?
N1 C2 1.3928(14) . ?
N1 C3 1.4302(14) . ?
N2 C9 1.3471(12) 2_655 ?
N2 C9 1.3471(12) . ?
C2 C2 1.346(2) 2_655 ?
C2 H2 0.920(18) . ?
C3 C4 1.3896(16) . ?
C3 C8 1.3929(17) . ?
C4 C5 1.3904(16) . ?
C4 H4 0.938(19) . ?
C5 C6 1.387(2) . ?
C6 C7 1.393(2) . ?
C6 H6 1.03(2) . ?
C7 C8 1.3896(18) . ?
C7 H7 0.95(2) . ?
C8 H8 0.94(2) . ?
C9 C10 1.3808(16) . ?
C9 H9 0.960(18) . ?
C10 C11 1.3902(14) . ?
C10 H10 0.91(2) . ?
C11 H11 0.93(3) . ?
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
C2 N1 C1 N1 -0.22(6) . . . 2_655 ?
C3 N1 C1 N1 -179.21(12) . . . 2_655 ?
C2 N1 C1 Pd1 179.78(6) . . . . ?
C3 N1 C1 Pd1 0.79(12) . . . . ?
C1 N1 C2 C2 0.58(15) . . . 2_655 ?
C3 N1 C2 C2 179.60(12) . . . 2_655 ?
C1 N1 C3 C4 140.71(10) . . . . ?
C2 N1 C3 C4 -38.17(15) . . . . ?
C1 N1 C3 C8 -40.36(15) . . . . ?
C2 N1 C3 C8 140.77(12) . . . . ?
C8 C3 C4 C5 1.06(17) . . . . ?
N1 C3 C4 C5 179.99(10) . . . . ?
C3 C4 C5 C6 0.56(18) . . . . ?
C3 C4 C5 Cl2 179.65(9) . . . . ?
C4 C5 C6 C7 -1.3(2) . . . . ?
Cl2 C5 C6 C7 179.60(11) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C6 C7 C8 C3 1.1(2) . . . . ?
C4 C3 C8 C7 -1.87(18) . . . . ?
N1 C3 C8 C7 179.23(11) . . . . ?
C9 N2 C9 C10 -0.27(8) 2_655 . . . ?
Pd1 N2 C9 C10 179.73(8) . . . . ?
N2 C9 C10 C11 0.53(16) . . . . ?
C9 C10 C11 C10 -0.25(8) . . . 2_655 ?
