Heteroleptic enantiopure Pd(ii)-complexes derived from halogen-substituted Schiff bases and 2-picolylamine: synthesis, experimental and computational characterization and investigation of the influence of chirality and halogen atoms on the anticancer activity
Kordestani, Nazanin; Amiri Rudbari, Hadi; Correia, Isabel; Valente, Andreia; Côrte-Real, Leonor; Islam, Mohammad Khairul; Micale, Nicola; Braun, Jason D.; Herbert, David E.; Tumanov, Nikolay; Wouters, Johan; Enamullah, Mohammed; New Journal of Chemistry 45 (2021) 9163–9180; doi:10.1039/D1NJ01491A

data_7060596
_publ_section_title
;
 Heteroleptic enantiopure Pd(ii)-complexes derived from
 halogen-substituted Schiff bases and 2-picolylamine: synthesis,
 experimental and computational characterization and investigation of the
 influence of chirality and halogen atoms on the anticancer activity
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9163
_journal_page_last               9180
_journal_paper_doi               10.1039/D1NJ01491A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C58 H57 Cl2 Fe N3'
_chemical_formula_sum            'C58 H57 Cl2 Fe N3'
_chemical_formula_weight         922.81
_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   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc24sc2d
_audit_creation_date             2019-04-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-11 deposited with the CCDC.	2021-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.3491(2)
_cell_length_b                   24.3546(2)
_cell_length_c                   17.18850(10)
_cell_measurement_reflns_used    32462
_cell_measurement_temperature    171(3)
_cell_measurement_theta_max      75.0560
_cell_measurement_theta_min      2.5260
_cell_volume                     10472.31(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      171(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -81.00 -56.00   0.50    1.92    --  -47.20  -3.00 152.00   50
  2  \w   -112.00 -26.00   0.50    7.67    --  -99.00  61.00  90.00  172
  3  \w    -73.00 -27.00   0.50    7.67    --  -99.00 125.00  60.00   92
  4  \w   -109.00  -7.00   0.50    1.92    --  -47.20   3.00 -30.00  204
  5  \w     14.00  39.00   0.50    1.92    --   47.20  -3.00 152.00   50
  6  \w     70.00  95.00   0.50    7.67    --  103.25  -3.00 152.00   50
  7  \w     81.00 106.00   0.50    7.67    --  103.25 -94.00  90.00   50
  8  \w     49.00  96.00   0.50    7.67    --  103.25 -94.00   0.00   94
  9  \w     38.00 119.00   0.50    1.92    --   47.20   3.00 -30.00  162
 10  \w     78.00 103.00   0.50    7.67    --  103.25 -94.00-120.00   50
 11  \w     35.00 143.00   0.50    7.67    --  103.25   3.00 -30.00  216
 12  \w     36.00  71.00   0.50    7.67    --  103.25 -94.00-120.00   70
 13  \w     31.00  98.00   0.50    7.67    --  103.25 -94.00 -30.00  134
 14  \w     32.00  58.00   0.50    7.67    --  103.25 -94.00  90.00   52
 15  \w     17.00  86.00   0.50    1.92    --   47.20-125.00   0.00  138
 16  \w    -23.00  61.00   0.50    1.92    --   47.20 -57.00  30.00  168
 17  \w   -117.00 -82.00   0.50    7.67    --  -99.00 125.00  60.00   70
 18  \w   -112.00 -30.00   0.50    7.67    --  -99.00  45.00  60.00  164
 19  \w   -167.00 -44.00   0.50    7.67    --  -99.00  -3.00 152.00  246
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577575000
_diffrn_orient_matrix_UB_12      0.0012654000
_diffrn_orient_matrix_UB_13      -0.0172991000
_diffrn_orient_matrix_UB_21      -0.0213611000
_diffrn_orient_matrix_UB_22      0.0023721000
_diffrn_orient_matrix_UB_23      -0.0890752000
_diffrn_orient_matrix_UB_31      -0.0003546000
_diffrn_orient_matrix_UB_32      0.0632000000
_diffrn_orient_matrix_UB_33      0.0037044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            82508
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.606
_diffrn_reflns_theta_min         2.532
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       needle
_exptl_crystal_F_000             3888
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1167
_refine_ls_number_reflns         20691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0420
_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/[\s^2^(Fo^2^)+(0.0603P)^2^+3.7828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16421
_reflns_number_total             20691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01491a2.cif
_cod_data_source_block           Fe3
_cod_depositor_comments
;
Adding full bibliography for 7060575--7060596.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C116 H114 Cl4 Fe2 N6'
_cod_original_formula_weight         1845.63
_cod_original_formula_moiety         '2(C58 H57 Cl2 Fe N3)'
_cod_original_formula_units_Z            4
_cod_database_code               7060596
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_usercomment     'C H N Fe Cl'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C32(H32), C17A(H17A), C17(H17), C32A(H32A), C56(H56), C53A(H53A), C56A(H56A),
 C53(H53)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C40(H40A,H40B), C25A(H25C,H25D), C39(H39A,
 H39B), C40A(H40C,H40D), C39A(H39C,H39D), C24A(H24C,H24D)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C14A(H14A), C4A(H4A), C12A(H12A), C5A(H5A), C45(H45),
 C6A(H6A), C19(H19), C44(H44), C30(H30), C19A(H19A), C42(H42), C4(H4), C34(H34),
  C20(H20), C6(H6), C30A(H30A), C43(H43), C22(H22), C27(H27), C5(H5), C21(H21),
 C20A(H20A), C34A(H34A), C27A(H27A), C51A(H51A), C28(H28), C49(H49), C49A(H49A),
  C51(H51), C37(H37), C29(H29), C50(H50), C35(H35), C28A(H28A), C22A(H22A),
 C37A(H37A), C50A(H50A), C21A(H21A), C36(H36), C36A(H36A), C29A(H29A),
 C35A(H35A), C45A(H45A), C42A(H42A), C44A(H44A), C43A(H43A)
2.d Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9(H9A,H9B,H9C), C16A(H16D,H16E,H16F), C16(H16A,H16B,
 H16C), C1A(H1AA,H1AB,H1AC), C1(H1A,H1B,H1C), C58(H58A,H58B,H58C), C54A(H54D,
 H54E,H54F), C58A(H58D,H58E,H58F), C57(H57A,H57B,H57C), C54(H54A,H54B,H54C),
 C55A(H55D,H55E,H55F), C55(H55A,H55B,H55C), C57A(H57D,H57E,H57F)
;
_shelx_res_checksum              25682
_shelx_fab_checksum              30014
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.143
_oxdiff_exptl_absorpt_empirical_full_min 0.508