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#$Date: 2025-10-06 12:05:18 +0300 (Mon, 06 Oct 2025) $
#$Revision: 302605 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/94/7719463.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.
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data_7719463
loop_
_publ_author_name
'Kovacevic, Anes'
'Parkin, Sean'
'Baltisberger, Jay H.'
_publ_section_title
;
 Synthesis of Pd(II)-NHC complexes via C-H oxidative addition of
 triazolium salts to Pd(0).
;
_journal_issue                   37
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13863
_journal_page_last               13868
_journal_paper_doi               10.1039/d5dt01695a
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C20 H22 Br2 N6 Pd'
_chemical_formula_sum            'C20 H22 Br2 N6 Pd'
_chemical_formula_weight         612.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2019/3 and CIFFIX'
_audit_update_record
;
2025-07-04 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.53(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.124(2)
_cell_length_b                   9.3713(19)
_cell_length_c                   11.796(2)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.81
_cell_volume                     1083.4(4)
_computing_cell_refinement       'APEX5 (Bruker-AXS, 2023)'
_computing_data_collection       'APEX5 (Bruker-AXS, 2023)'
_computing_data_reduction        'APEX5 (Bruker-AXS, 2023)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15508
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.812
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    4.564
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_description       'wedge-shaped shard'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
; 
Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.024(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0178
_refine_ls_R_factor_gt           0.0155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0235P)²+0.0144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0401
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                2451
_reflns_number_total             2627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01695a2.cif
_cod_data_source_block           m25192
_cod_depositor_comments
'Adding full bibliography for 7719463--7719465.cif.'
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               7719463
_shelx_shelxl_version_number     2019/3
_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   0.462
_shelx_estimated_absorpt_t_max   0.804
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount, scan truncation etc. These account, by and large, for the difference 
between SHELX estimates of Tmin and Tmax and the _exptl_absorpt_correction_ 
values. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-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 0.52548(5) 0.500000 0.01256(7) Uani 1 2 d S T P . .
Br1 Br 0.500000 0.78679(3) 0.500000 0.01722(14) Uani 1 2 d S T P . .
Br2 Br 0.500000 0.26519(3) 0.500000 0.02084(16) Uani 1 2 d S T P . .
N1 N 0.8019(2) 0.5757(2) 0.57454(19) 0.0153(5) Uani 1 1 d . . . . .
N2 N 0.9183(2) 0.5725(3) 0.6647(2) 0.0176(5) Uani 1 1 d . . . . .
N3 N 0.7377(2) 0.4942(2) 0.71819(19) 0.0153(5) Uani 1 1 d . . . . .
C1 C 0.6905(2) 0.5295(5) 0.60321(18) 0.0149(4) Uani 1 1 d . . . . .
C2 C 0.8746(2) 0.5207(5) 0.75156(19) 0.0170(4) Uani 1 1 d . . . . .
H2 H 0.930674 0.503784 0.827914 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6585(3) 0.4249(3) 0.7913(3) 0.0199(6) Uani 1 1 d . . . . .
H3A H 0.719954 0.405070 0.869254 0.024 Uiso 1 1 calc R U . . .
H3B H 0.624473 0.332158 0.755459 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5384(3) 0.5110(4) 0.8078(2) 0.0179(6) Uani 1 1 d . . . . .
C5 C 0.4219(3) 0.4380(4) 0.8154(3) 0.0239(6) Uani 1 1 d . . . . .
H5 H 0.416811 0.337693 0.803265 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3129(3) 0.5095(5) 0.8403(2) 0.0277(8) Uani 1 1 d . . . . .
H6 H 0.233923 0.458050 0.846038 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3188(3) 0.6558(4) 0.8570(3) 0.0292(7) Uani 1 1 d . . . . .
H7 H 0.244818 0.705103 0.875266 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4333(4) 0.7291(4) 0.8466(3) 0.0328(8) Uani 1 1 d . . . . .
H8 H 0.436893 0.829845 0.855732 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5433(3) 0.6574(4) 0.8232(3) 0.0259(7) Uani 1 1 d . . . . .
H9 H 0.622218 0.708936 0.817561 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8109(3) 0.6303(3) 0.4609(2) 0.0230(6) Uani 1 1 d . . . . .
H10A H 0.875718 0.572423 0.431449 0.035 Uiso 1 1 calc R U . . .
H10B H 0.842286 0.729625 0.469386 0.035 Uiso 1 1 calc R U . . .
H10C H 0.720847 0.625713 0.405680 0.035 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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 C1 177.8(3) 2_656 . ?
C1 Pd1 Br2 91.08(13) 2_656 . ?
C1 Pd1 Br2 91.08(13) . . ?
C1 Pd1 Br1 88.92(13) 2_656 . ?
C1 Pd1 Br1 88.92(13) . . ?
Br2 Pd1 Br1 180.0 . . ?
C1 N1 N2 114.44(19) . . ?
C1 N1 C10 126.9(2) . . ?
N2 N1 C10 118.6(2) . . ?
C2 N2 N1 102.8(2) . . ?
C1 N3 C2 108.7(2) . . ?
C1 N3 C3 125.9(2) . . ?
C2 N3 C3 125.2(2) . . ?
N1 C1 N3 102.97(19) . . ?
N1 C1 Pd1 126.87(18) . . ?
N3 C1 Pd1 130.09(18) . . ?
N2 C2 N3 111.1(2) . . ?
N2 C2 H2 124.4 . . ?
N3 C2 H2 124.4 . . ?
N3 C3 C4 114.5(2) . . ?
N3 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
N3 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C9 C4 C5 119.0(3) . . ?
C9 C4 C3 122.9(3) . . ?
C5 C4 C3 118.0(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 120.2(3) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 2.006(2) 2_656 ?
Pd1 C1 2.006(2) . ?
Pd1 Br2 2.4393(8) . ?
Pd1 Br1 2.4488(8) . ?
N1 C1 1.329(3) . ?
N1 N2 1.375(3) . ?
N1 C10 1.459(3) . ?
N2 C2 1.308(3) . ?
N3 C1 1.361(3) . ?
N3 C2 1.365(3) . ?
N3 C3 1.469(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.511(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.383(5) . ?
C4 C5 1.386(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 Br1 0.95 2.83 3.625(3) 141.3 3_545 yes
C3 H3A Br1 0.99 3.07 3.927(3) 145.0 3_545 yes
C3 H3B Br2 0.99 3.03 3.723(3) 128.4 . yes
C3 H3B N2 0.99 2.68 3.462(4) 135.7 4_646 yes
C10 H10A N2 0.98 2.61 3.470(4) 146.3 2_756 yes
C10 H10C Br1 0.98 3.12 3.605(3) 111.8 . yes
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
C1 N1 N2 C2 0.5(4) . . . . ?
C10 N1 N2 C2 179.2(3) . . . . ?
N2 N1 C1 N3 -0.2(4) . . . . ?
C10 N1 C1 N3 -178.8(3) . . . . ?
N2 N1 C1 Pd1 177.0(2) . . . . ?
C10 N1 C1 Pd1 -1.6(5) . . . . ?
C2 N3 C1 N1 -0.2(4) . . . . ?
C3 N3 C1 N1 -174.3(2) . . . . ?
C2 N3 C1 Pd1 -177.2(3) . . . . ?
C3 N3 C1 Pd1 8.7(5) . . . . ?
N1 N2 C2 N3 -0.6(4) . . . . ?
C1 N3 C2 N2 0.5(4) . . . . ?
C3 N3 C2 N2 174.7(3) . . . . ?
C1 N3 C3 C4 -62.7(4) . . . . ?
C2 N3 C3 C4 124.1(3) . . . . ?
N3 C3 C4 C9 -39.0(4) . . . . ?
N3 C3 C4 C5 145.3(3) . . . . ?
C9 C4 C5 C6 -1.4(4) . . . . ?
C3 C4 C5 C6 174.5(3) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C9 -1.8(5) . . . . ?
C5 C4 C9 C8 0.5(4) . . . . ?
C3 C4 C9 C8 -175.2(3) . . . . ?
C7 C8 C9 C4 1.1(5) . . . . ?
