#------------------------------------------------------------------------------
#$Date: 2025-07-10 14:18:13 +0300 (Thu, 10 Jul 2025) $
#$Revision: 301209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567074.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_1567074
loop_
_publ_author_name
'Bermúdez-Puente, Brais'
'Adrio, Luis A.'
'Lucio-Martínez, Fátima'
'Reigosa, Francisco'
'Ortigueira, Juan M.'
'Vila, José M.'
_publ_section_title
;
 Imine Palladacycles: Synthesis, Structural Analysis and Application in
 Suzuki--Miyaura Cross Coupling in Semi-Aqueous Media
;
_journal_issue                   10
_journal_name_full               Molecules
_journal_page_first              3146
_journal_paper_doi               10.3390/molecules27103146
_journal_volume                  27
_journal_year                    2022
_chemical_formula_moiety         'C32 H30 Br2 Cl2 N2 O6 Pd2'
_chemical_formula_sum            'C32 H30 Br2 Cl2 N2 O6 Pd2'
_chemical_formula_weight         982.147
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.0378(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.9156(3)
_cell_length_b                   3.92009(8)
_cell_length_c                   30.0833(6)
_cell_measurement_reflns_used    4951
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      26.482
_cell_measurement_theta_min      2.24
_cell_volume                     1604.97(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9919
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9919
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            21117
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9919
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.61
_diffrn_reflns_theta_min         1.50
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.825
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0655 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.8404.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_description       prism
_exptl_crystal_F_000             956.318
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.8099
_refine_diff_density_min         -0.8814
_refine_diff_density_rms         0.2063
_refine_ls_d_res_high            0.7933
_refine_ls_d_res_low             13.6096
_refine_ls_goodness_of_fit_ref   1.0355
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0355
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0206P)²+1.5237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0541
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              4
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                2674
_reflns_number_total             3313
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            2011vi11bbp10_0m.cif
_cod_data_source_block           2011vi11bbp10_0m
_cod_depositor_comments
;

2025-07-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C64 H60 Br4 Cl4 N4 O12 Pd4'
_cod_original_formula_weight         1964.295
_cod_original_formula_moiety         '2(C32 H30 Br2 Cl2 N2 O6 Pd2)'
_cod_original_formula_units_Z            1
_cod_database_code               1567074
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C9(H4), C12(H9), C7(H10), C5(H13), C13(H14), C10(H16)
1.b Idealised Me refined as rotating group:
 C15(H8a,H8b,H8c), C16(H15a,H15b,H15c), C14(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
Pd1 Pd 0.928639(17) 0.81016(7) 0.451245(8) 0.01139(7) Uani 1.000000 .
Br2 Br 1.25460(2) 0.85397(10) 0.278670(12) 0.02460(10) Uani 1.000000 .
Cl1 Cl 0.91141(5) 0.9100(2) 0.52566(3) 0.01365(18) Uani 1.000000 .
O1 O 0.65853(15) 0.3310(6) 0.32068(7) 0.0194(5) Uani 1.000000 .
O2 O 0.52952(15) 0.1334(6) 0.37600(8) 0.0177(5) Uani 1.000000 .
O3 O 0.58229(15) 0.2294(6) 0.46700(8) 0.0177(5) Uani 1.000000 .
N1 N 0.92789(17) 0.7345(7) 0.38381(8) 0.0127(6) Uani 1.000000 .
C1 C 0.7709(2) 0.5409(9) 0.38591(11) 0.0130(7) Uani 1.000000 .
C2 C 0.6797(2) 0.3940(9) 0.36669(11) 0.0160(8) Uani 1.000000 .
C3 C 0.6164(2) 0.2988(9) 0.39459(11) 0.0144(7) Uani 1.000000 .
C4 C 0.6459(2) 0.3479(9) 0.44164(11) 0.0146(7) Uani 1.000000 .
C5 C 0.7358(2) 0.5020(9) 0.46050(11) 0.0134(7) Uani 1.000000 .
H13 H 0.7536(2) 0.5404(9) 0.49234(11) 0.0161(9) Uiso 1.000000 R
C6 C 0.7984(2) 0.5978(8) 0.43293(11) 0.0115(7) Uani 1.000000 .
C7 C 0.8443(2) 0.6179(8) 0.36091(11) 0.0142(7) Uani 1.000000 .
H10 H 0.8330(2) 0.5859(8) 0.32893(11) 0.0171(9) Uiso 1.000000 R
C8 C 1.0059(2) 0.7913(8) 0.36072(11) 0.0122(7) Uani 1.000000 .
C9 C 0.9898(2) 0.9515(9) 0.31866(11) 0.0141(7) Uani 1.000000 .
H4 H 0.9268(2) 1.0433(9) 0.30597(11) 0.0169(9) Uiso 1.000000 R
C10 C 1.0649(2) 0.9782(9) 0.29515(11) 0.0149(7) Uani 1.000000 .
H16 H 1.0539(2) 1.0876(9) 0.26635(11) 0.0179(9) Uiso 1.000000 R
C11 C 1.1559(2) 0.8447(9) 0.31391(11) 0.0147(7) Uani 1.000000 .
C12 C 1.1748(2) 0.6953(9) 0.35673(11) 0.0153(7) Uani 1.000000 .
H9 H 1.2385(2) 0.6114(9) 0.36973(11) 0.0184(9) Uiso 1.000000 R
C13 C 1.0992(2) 0.6706(9) 0.38022(11) 0.0147(7) Uani 1.000000 .
H14 H 1.1111(2) 0.5711(9) 0.40966(11) 0.0177(9) Uiso 1.000000 R
C14 C 0.5756(3) 0.5130(11) 0.29541(12) 0.0273(9) Uani 1.000000 .
H1a H 0.5721(10) 0.481(5) 0.26280(12) 0.0409(14) Uiso 1.000000 GR
H1b H 0.5153(3) 0.426(4) 0.3033(6) 0.0409(14) Uiso 1.000000 GR
H1c H 0.5826(9) 0.7564(13) 0.3028(6) 0.0409(14) Uiso 1.000000 GR
C15 C 0.4420(2) 0.3195(10) 0.37939(12) 0.0218(8) Uani 1.000000 .
H8a H 0.3854(3) 0.222(4) 0.3583(6) 0.0327(12) Uiso 1.000000 GR
H8b H 0.4314(9) 0.304(5) 0.4105(2) 0.0327(12) Uiso 1.000000 GR
H8c H 0.4497(7) 0.5594(15) 0.3717(7) 0.0327(12) Uiso 1.000000 GR
C16 C 0.6123(2) 0.2615(9) 0.51516(11) 0.0210(8) Uani 1.000000 .
H15a H 0.6215(15) 0.5032(10) 0.52326(12) 0.0315(12) Uiso 1.000000 GR
H15b H 0.5617(8) 0.164(5) 0.52969(12) 0.0315(12) Uiso 1.000000 GR
H15c H 0.6743(9) 0.139(5) 0.52559(14) 0.0315(12) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Pd -0.98845 1.01473 19.33190 15.50170 5.29537 0.60584 0.69866 7.98929 25.20520
76.89860 5.26593 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
N1 Pd1 Cl1 173.79(7) . . ?
N1 Pd1 Cl1 99.35(7) . 3_776 ?
C6 Pd1 Cl1 93.83(9) . . ?
C6 Pd1 Cl1 178.38(9) . 3_776 ?
C6 Pd1 N1 81.20(11) . . ?
C14 O1 C2 115.1(3) . . ?
C15 O2 C3 114.5(2) . . ?
C16 O3 C4 116.8(2) . . ?
C7 N1 Pd1 113.2(2) . . ?
C7 N1 C8 118.9(3) . . ?
C8 N1 Pd1 127.9(2) . . ?
C6 C1 C2 120.9(3) . . ?
C7 C1 C2 123.8(3) . . ?
C7 C1 C6 115.1(3) . . ?
C1 C2 O1 118.3(3) . . ?
C1 C2 C3 119.6(3) . . ?
C3 C2 O1 122.0(3) . . ?
C2 C3 O2 119.5(3) . . ?
C4 C3 O2 121.3(3) . . ?
C4 C3 C2 119.0(3) . . ?
C3 C4 O3 115.5(3) . . ?
C5 C4 O3 123.3(3) . . ?
C5 C4 C3 121.2(3) . . ?
C4 C5 C6 119.9(3) . . ?
H13 C5 C4 120.03(19) . . ?
H13 C5 C6 120.03(19) . . ?
C1 C6 Pd1 113.0(2) . . ?
C5 C6 Pd1 127.6(2) . . ?
C5 C6 C1 119.4(3) . . ?
C1 C7 N1 117.0(3) . . ?
C1 C7 H10 121.48(19) . . ?
H10 C7 N1 121.48(18) . . ?
C9 C8 N1 121.4(3) . . ?
C13 C8 N1 118.7(3) . . ?
C13 C8 C9 119.8(3) . . ?
C8 C9 H4 119.84(18) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H4 119.8(2) . . ?
H16 C10 C9 120.3(2) . . ?
H16 C10 C11 120.32(19) . . ?
C11 C10 C9 119.4(3) . . ?
C10 C11 Br2 118.2(3) . . ?
C10 C11 C12 121.3(3) . . ?
C12 C11 Br2 120.4(2) . . ?
C11 C12 H9 120.51(18) . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H9 120.51(19) . . ?
C12 C13 C8 120.1(3) . . ?
H14 C13 C8 119.95(18) . . ?
H14 C13 C12 119.95(19) . . ?
H1a C14 O1 109.5 . . ?
H1b C14 O1 109.5 . . ?
H1b C14 H1a 109.5 . . ?
H1c C14 O1 109.5 . . ?
H1c C14 H1a 109.5 . . ?
H1c C14 H1b 109.5 . . ?
H8a C15 O2 109.5 . . ?
H8b C15 O2 109.5 . . ?
H8b C15 H8a 109.5 . . ?
H8c C15 O2 109.5 . . ?
H8c C15 H8a 109.5 . . ?
H8c C15 H8b 109.5 . . ?
H15a C16 O3 109.5 . . ?
H15b C16 O3 109.5 . . ?
H15b C16 H15a 109.5 . . ?
H15c C16 O3 109.5 . . ?
H15c C16 H15a 109.5 . . ?
H15c C16 H15b 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 Cl1 2.4485(8) 3_776 ?
Pd1 Cl1 2.3338(8) . ?
Pd1 N1 2.048(3) . ?
Pd1 C6 1.966(3) . ?
Br2 C11 1.902(3) . ?
O1 C2 1.376(4) . ?
O1 C14 1.433(4) . ?
O2 C3 1.383(4) . ?
O2 C15 1.441(4) . ?
O3 C4 1.365(4) . ?
O3 C16 1.427(4) . ?
N1 C7 1.304(4) . ?
N1 C8 1.423(4) . ?
C2 C1 1.404(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.402(5) . ?
C4 C5 1.398(4) . ?
C5 H13 0.9500 . ?
C6 C1 1.404(4) . ?
C6 C5 1.375(4) . ?
C7 C1 1.422(4) . ?
C7 H10 0.9500 . ?
C8 C13 1.392(4) . ?
C9 C8 1.388(4) . ?
C9 H4 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H16 0.9500 . ?
C11 C10 1.378(4) . ?
C12 C11 1.389(5) . ?
C12 H9 0.9500 . ?
C12 C13 1.388(4) . ?
C13 H14 0.9500 . ?
C14 H1a 0.9800 . ?
C14 H1b 0.9800 . ?
C14 H1c 0.9800 . ?
C15 H8a 0.9800 . ?
C15 H8b 0.9800 . ?
C15 H8c 0.9800 . ?
C16 H15a 0.9800 . ?
C16 H15b 0.9800 . ?
C16 H15c 0.9800 . ?
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
Pd1 N1 C7 C1 -4.1(2) . . . . ?
Pd1 N1 C8 C9 -135.9(3) . . . . ?
Pd1 N1 C8 C13 46.7(3) . . . . ?
Pd1 C6 C1 C2 -179.4(2) . . . . ?
Pd1 C6 C1 C7 5.2(3) . . . . ?
Pd1 C6 C5 C4 -178.9(3) . . . . ?
Br2 C11 C10 C9 175.2(3) . . . . ?
Br2 C11 C12 C13 -175.4(3) . . . . ?
O1 C2 C1 C6 -177.3(3) . . . . ?
O1 C2 C1 C7 -2.3(4) . . . . ?
O1 C2 C3 O2 0.5(4) . . . . ?
O1 C2 C3 C4 175.3(3) . . . . ?
O2 C3 C2 C1 -175.7(3) . . . . ?
O2 C3 C4 O3 -1.5(3) . . . . ?
O2 C3 C4 C5 177.2(3) . . . . ?
O3 C4 C3 C2 -176.2(3) . . . . ?
O3 C4 C5 C6 176.4(3) . . . . ?
N1 C7 C1 C6 -0.6(3) . . . . ?
N1 C8 C9 C10 -174.5(3) . . . . ?
N1 C8 C13 C12 174.4(3) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C7 N1 -175.9(3) . . . . ?
C2 C3 C4 C5 2.5(4) . . . . ?
C6 C5 C4 C3 -2.2(4) . . . . ?
C8 C13 C12 C11 0.6(4) . . . . ?
C9 C8 C13 C12 -3.1(4) . . . . ?
C9 C10 C11 C12 -2.5(4) . . . . ?
