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#$Date: 2024-08-05 21:58:33 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293845 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/64/7716425.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_7716425
loop_
_publ_author_name
'Li, Haobin'
'Zhang, Bo'
'Feng, Rui'
'Guo, Shuai'
_publ_section_title
;
 An N-heterocyclic carbene-based pincer system of palladium and its
 versatile reactivity under oxidizing conditions.
;
_journal_issue                   27
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11470
_journal_page_last               11480
_journal_paper_doi               10.1039/d4dt00980k
_journal_volume                  53
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H29 Br N4 Pd'
_chemical_formula_weight         535.80
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-10-03 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7735(2)
_cell_length_b                   8.7735(2)
_cell_length_c                   27.5380(7)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.955
_cell_measurement_theta_min      4.873
_cell_volume                     2119.72(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.994
_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       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18718
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.212
_exptl_absorpt_coefficient_mu    2.776
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.014(9)
_refine_ls_extinction_coef       0.0216(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0159
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0136P)²+0.3223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0386
_refine_ls_wR_factor_ref         0.0388
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2019
_reflns_number_total             2075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00980k2.cif
_cod_data_source_block           mo_ddz21021_0m
_cod_depositor_comments
'Adding full bibliography for 7716424--7716428.cif.'
_cod_original_cell_volume        2119.72(11)
_cod_database_code               7716425
_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   0.665
_shelx_estimated_absorpt_t_max   0.750
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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 0.51556(2) 0.48444(2) 0.7500 0.01820(10) Uani 1 2 d S T P . .
Br1 Br 0.30974(3) 0.69026(3) 0.7500 0.02495(12) Uani 1 2 d S T P . .
N1 N 0.8157(3) 0.6154(3) 0.72369(8) 0.0228(5) Uani 1 1 d . . . . .
N2 N 0.6621(2) 0.6855(2) 0.66788(7) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.6776(3) 0.3224(3) 0.7500 0.0227(8) Uani 1 2 d S T P . .
C2 C 0.8298(3) 0.3598(3) 0.75842(9) 0.0242(6) Uani 1 1 d . . . . .
C3 C 0.9413(3) 0.2465(4) 0.75950(10) 0.0325(7) Uani 1 1 d . . . . .
H3 H 1.0428 0.2722 0.7667 0.039 Uiso 1 1 calc R U . . .
C4 C 0.9031(3) 0.0969(3) 0.7500 0.0349(10) Uani 1 2 d S T P . .
H4 H 0.9789 0.0211 0.7500 0.042 Uiso 1 2 calc R U P . .
C5 C 0.8755(3) 0.5253(3) 0.76452(9) 0.0273(6) Uani 1 1 d . . . . .
H5A H 0.8348 0.5649 0.7952 0.033 Uiso 1 1 calc R U . . .
H5B H 0.9869 0.5336 0.7655 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6676(3) 0.6069(3) 0.71017(9) 0.0213(6) Uani 1 1 d . . . . .
C7 C 0.9009(3) 0.6979(3) 0.69121(10) 0.0260(6) Uani 1 1 d . . . . .
H7 H 1.0057 0.7194 0.6933 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8055(3) 0.7414(3) 0.65600(10) 0.0288(7) Uani 1 1 d . . . . .
H8 H 0.8306 0.7991 0.6284 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5268(3) 0.6983(3) 0.63689(10) 0.0253(6) Uani 1 1 d . . . . .
H9A H 0.4379 0.6611 0.6548 0.030 Uiso 1 1 calc R U . . .
H9B H 0.5402 0.6331 0.6083 0.030 Uiso 1 1 calc R U . . .
C10 C 0.4969(4) 0.8598(3) 0.62034(12) 0.0352(7) Uani 1 1 d . . . . .
H10A H 0.5810 0.8937 0.5996 0.042 Uiso 1 1 calc R U . . .
H10B H 0.4932 0.9271 0.6487 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3465(4) 0.8729(4) 0.59219(11) 0.0373(8) Uani 1 1 d . . . . .
H11A H 0.3431 0.9728 0.5763 0.045 Uiso 1 1 calc R U . . .
H11B H 0.3455 0.7952 0.5666 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2065(4) 0.8549(4) 0.62235(12) 0.0447(9) Uani 1 1 d . . . . .
H12A H 0.1171 0.8725 0.6024 0.067 Uiso 1 1 calc R U . . .
H12B H 0.2083 0.9281 0.6487 0.067 Uiso 1 1 calc R U . . .
H12C H 0.2029 0.7525 0.6355 0.067 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'
Br Br -0.2901 2.4595 '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'
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 C6 84.83(7) . 8_666 ?
C1 Pd1 C6 84.83(7) . . ?
C6 Pd1 C6 169.65(14) 8_666 . ?
C1 Pd1 Br1 180.000(13) . . ?
C6 Pd1 Br1 95.17(7) 8_666 . ?
C6 Pd1 Br1 95.17(7) . . ?
C6 N1 C7 111.9(2) . . ?
C6 N1 C5 121.5(2) . . ?
C7 N1 C5 126.0(2) . . ?
C6 N2 C8 110.5(2) . . ?
C6 N2 C9 124.6(2) . . ?
C8 N2 C9 124.7(2) . . ?
C2 C1 C2 118.6(3) . 8_666 ?
C2 C1 Pd1 120.70(16) . . ?
C2 C1 Pd1 120.70(16) 8_666 . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 C5 119.9(2) . . ?
C3 C2 C5 119.6(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C3 119.8(4) 8_666 . ?
C3 C4 H4 120.1 8_666 . ?
C3 C4 H4 120.1 . . ?
N1 C5 C2 109.6(2) . . ?
N1 C5 H5A 109.7 . . ?
C2 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C2 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 N2 104.0(2) . . ?
N1 C6 Pd1 120.68(18) . . ?
N2 C6 Pd1 135.19(19) . . ?
C8 C7 N1 106.4(2) . . ?
C8 C7 H7 126.8 . . ?
N1 C7 H7 126.8 . . ?
C7 C8 N2 107.2(2) . . ?
C7 C8 H8 126.4 . . ?
N2 C8 H8 126.4 . . ?
N2 C9 C10 112.8(2) . . ?
N2 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 111.8(3) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 114.8(2) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 2.011(3) . ?
Pd1 C6 2.034(3) 8_666 ?
Pd1 C6 2.034(3) . ?
Pd1 Br1 2.5537(4) . ?
N1 C6 1.354(3) . ?
N1 C7 1.372(4) . ?
N1 C5 1.471(3) . ?
N2 C6 1.354(3) . ?
N2 C8 1.389(3) . ?
N2 C9 1.466(3) . ?
C1 C2 1.394(3) . ?
C1 C2 1.394(3) 8_666 ?
C2 C3 1.395(4) . ?
C2 C5 1.516(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9400 . ?
C4 C3 1.380(4) 8_666 ?
C4 H4 0.9400 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C7 C8 1.337(4) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C10 1.511(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.535(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.491(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
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
C9 H9A Br1 0.98 2.86 3.652(3) 138.1 .
C7 H7 Br1 0.94 3.10 3.936(3) 148.8 1_655
C9 H9A Br1 0.98 2.86 3.652(3) 138.1 .
C7 H7 Br1 0.94 3.10 3.936(3) 148.8 1_655
C7 H7 Br1 0.94 3.10 3.936(3) 148.8 1_655
C9 H9A Br1 0.98 2.86 3.652(3) 138.1 .
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 C1 C2 C3 -1.50(18) 8_666 . . . ?
Pd1 C1 C2 C3 178.50(18) . . . . ?
C2 C1 C2 C5 176.1(2) 8_666 . . . ?
Pd1 C1 C2 C5 -3.9(2) . . . . ?
C1 C2 C3 C4 3.0(4) . . . . ?
C5 C2 C3 C4 -174.61(19) . . . . ?
C2 C3 C4 C3 -1.51(18) . . . 8_666 ?
C6 N1 C5 C2 50.3(3) . . . . ?
C7 N1 C5 C2 -119.9(3) . . . . ?
C1 C2 C5 N1 -51.5(3) . . . . ?
C3 C2 C5 N1 126.2(2) . . . . ?
C7 N1 C6 N2 0.5(3) . . . . ?
C5 N1 C6 N2 -171.0(2) . . . . ?
C7 N1 C6 Pd1 177.53(17) . . . . ?
C5 N1 C6 Pd1 6.1(3) . . . . ?
C8 N2 C6 N1 -0.1(3) . . . . ?
C9 N2 C6 N1 174.9(2) . . . . ?
C8 N2 C6 Pd1 -176.5(2) . . . . ?
C9 N2 C6 Pd1 -1.5(4) . . . . ?
C6 N1 C7 C8 -0.6(3) . . . . ?
C5 N1 C7 C8 170.3(3) . . . . ?
N1 C7 C8 N2 0.5(3) . . . . ?
C6 N2 C8 C7 -0.2(3) . . . . ?
C9 N2 C8 C7 -175.2(3) . . . . ?
C6 N2 C9 C10 133.5(3) . . . . ?
C8 N2 C9 C10 -52.1(4) . . . . ?
N2 C9 C10 C11 -174.4(2) . . . . ?
C9 C10 C11 C12 70.6(4) . . . . ?
