#------------------------------------------------------------------------------
#$Date: 2024-07-05 19:31:07 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/61/7716171.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_7716171
loop_
_publ_author_name
'Forooghi, Kimia'
'Amiri Rudbari, Hadi'
'Stagno, Claudio'
'Iraci, Nunzio'
'Cuevas-Vicario, José V'
'Kordestani, Nazanin'
'Schirmeister, Tanja'
'Efferth, Thomas'
'Omer, Ejlal A.'
'Moini, Nakisa'
'Aryaeifar, Mahnaz'
'Blacque, Olivier'
'Azadbakht, Reza'
'Micale, Nicola'
_publ_section_title
;
 Structural features and antiproliferative activity of Pd(II) complexes
 with halogenated ligands: a comparative study between Schiff base and
 reduced Schiff base complexes.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10571
_journal_page_last               10591
_journal_paper_doi               10.1039/d4dt00132j
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C14 H11 Br2 Cl N2 O Pd'
_chemical_formula_sum            'C14 H11 Br2 Cl N2 O Pd'
_chemical_formula_weight         524.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-08-28 deposited with the CCDC.	2024-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.204(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0229(3)
_cell_length_b                   7.48770(10)
_cell_length_c                   15.3898(3)
_cell_measurement_reflns_used    14390
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.2200
_cell_measurement_theta_min      3.1580
_cell_volume                     1566.34(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00-150.00   96
  2  ω    -69.00  28.00   1.00    1.00    --  -42.61  57.00-180.00   97
  3  ω      6.00  83.00   1.00    1.00    --   42.61 -99.00  60.00   77
  4  ω     83.00 178.00   1.00    4.00    --  111.00  61.00-150.00   95
  5  ω    103.00 178.00   1.00    4.00    --  111.00  77.00 -90.00   75
  6  ω     36.00 109.00   1.00    4.00    --  111.00-111.00  60.00   73
  7  ω     36.00 109.00   1.00    4.00    --  111.00-111.00-150.00   73
  8  ω     36.00 135.00   1.00    4.00    --  111.00 -30.00 -30.00   99
  9  ω     30.00 107.00   1.00    4.00    --  111.00 -94.00 -30.00   77
 10  ω     36.00 109.00   1.00    4.00    --  111.00-111.00  30.00   73
 11  ω     40.00 135.00   1.00    4.00    --  111.00 -45.00-150.00   95
 12  ω    103.00 178.00   1.00    4.00    --  111.00  77.00-180.00   75
 13  ω     87.00 178.00   1.00    4.00    --  111.00  45.00 150.00   91
 14  ω     41.00 139.00   1.00    4.00    --  111.00 -61.00  60.00   98
 15  ω   -113.00 -16.00   1.00    1.00    --  -42.61 -57.00 -30.00   97
 16  ω   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00  30.00   96
 17  ω   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00 120.00   96
 18  ω     83.00 176.00   1.00    4.00    --  111.00  61.00 -30.00   93
 19  ω     87.00 178.00   1.00    4.00    --  111.00  45.00  90.00   91
 20  ω     87.00 178.00   1.00    4.00    --  111.00  30.00  30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0904846000
_diffrn_orient_matrix_UB_12      0.0621185000
_diffrn_orient_matrix_UB_13      0.0898942000
_diffrn_orient_matrix_UB_21      0.0666048000
_diffrn_orient_matrix_UB_22      -0.0407825000
_diffrn_orient_matrix_UB_23      -0.0508484000
_diffrn_orient_matrix_UB_31      -0.0149997000
_diffrn_orient_matrix_UB_32      0.1917303000
_diffrn_orient_matrix_UB_33      -0.0398349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16096
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.462
_diffrn_reflns_theta_min         3.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    17.099
_exptl_absorpt_correction_T_max  0.523
_exptl_absorpt_correction_T_min  0.116
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.226
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.00053(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0173
_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)+(0.0215P)²+1.4128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3177
_reflns_number_total             3209
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00132j2.cif
_cod_data_source_block           hadi0709
_cod_depositor_comments
'Adding full bibliography for 7716171--7716173.cif.'
_cod_database_code               7716171
_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_max   0.482
_shelx_estimated_absorpt_t_min   0.080
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br 0.51577(2) 0.27073(4) 0.63252(2) 0.03541(8) Uani 1 1 d . . . . .
Br2 Br 0.21132(2) 0.54766(4) 0.29313(2) 0.03769(8) Uani 1 1 d . . . . .
C1 C 0.32169(15) 0.3387(3) 0.61131(14) 0.0193(4) Uani 1 1 d . . . . .
C2 C 0.38368(15) 0.3440(3) 0.56266(15) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.35183(17) 0.4030(3) 0.46954(15) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.395328 0.405639 0.439327 0.032 Uiso 1 1 calc R U . . .
C4 C 0.25453(17) 0.4588(3) 0.42044(14) 0.0257(4) Uani 1 1 d . . . . .
C5 C 0.19099(15) 0.4551(3) 0.46305(14) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.124601 0.491727 0.427989 0.028 Uiso 1 1 calc R U . . .
C6 C 0.22399(14) 0.3971(3) 0.55890(14) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.15189(14) 0.3922(3) 0.59785(14) 0.0200(4) Uani 1 1 d . . . . .
H7 H 0.085488 0.411734 0.553512 0.024 Uiso 1 1 calc R U . . .
C8 C 0.07968(14) 0.3623(3) 0.70580(15) 0.0224(4) Uani 1 1 d . . . . .
H8A H 0.022085 0.319930 0.648319 0.027 Uiso 1 1 calc R U . . .
H8B H 0.065581 0.485231 0.720146 0.027 Uiso 1 1 calc R U . . .
C9 C 0.09521(15) 0.2414(3) 0.79049(15) 0.0239(4) Uani 1 1 d . . . . .
H9A H 0.030872 0.216798 0.791414 0.029 Uiso 1 1 calc R U . . .
H9B H 0.123016 0.126162 0.782278 0.029 Uiso 1 1 calc R U . . .
C10 C 0.16287(16) 0.3230(3) 0.88426(15) 0.0227(4) Uani 1 1 d . . . . .
C11 C 0.13392(18) 0.3484(3) 0.95782(17) 0.0295(5) Uani 1 1 d . . . . .
H11 H 0.070314 0.311329 0.949519 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1970(2) 0.4273(3) 1.04300(17) 0.0337(5) Uani 1 1 d . . . . .
H12 H 0.177799 0.442796 1.093903 0.040 Uiso 1 1 calc R U . . .
C13 C 0.28857(19) 0.4833(3) 1.05293(16) 0.0311(5) Uani 1 1 d . . . . .
H13 H 0.333099 0.539141 1.110485 0.037 Uiso 1 1 calc R U . . .
C14 C 0.31415(16) 0.4565(3) 0.97767(15) 0.0247(4) Uani 1 1 d . . . . .
H14 H 0.376707 0.496348 0.984113 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.46054(3) 0.28608(7) 0.90721(3) 0.02666(11) Uani 1 1 d . . . . .
N1 N 0.16707(12) 0.3645(2) 0.68535(12) 0.0185(3) Uani 1 1 d . . . . .
N2 N 0.25313(13) 0.3755(2) 0.89509(12) 0.0207(3) Uani 1 1 d . . . . .
O1 O 0.35796(10) 0.2795(2) 0.69914(10) 0.0224(3) Uani 1 1 d . . . . .
Pd1 Pd 0.30132(2) 0.32862(2) 0.79211(2) 0.01675(6) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0141
-1 0 -1 0.0331
-1 0 1 0.0642
1 0 -1 0.0642
-2 -5 2 0.1496
2 5 -2 0.1196
-3 4 -4 0.0985
-5 4 4 0.1203
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
C6 C1 C2 116.46(18) . . ?
O1 C1 C2 118.56(19) . . ?
O1 C1 C6 124.97(19) . . ?
C1 C2 Br1 117.15(16) . . ?
C3 C2 Br1 120.03(16) . . ?
C3 C2 C1 122.8(2) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.7(2) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Br2 118.85(16) . . ?
C5 C4 Br2 119.90(17) . . ?
C5 C4 C3 121.23(19) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.06(19) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 122.45(18) . . ?
C5 C6 C1 120.71(19) . . ?
C5 C6 C7 116.76(18) . . ?
C6 C7 H7 116.2 . . ?
N1 C7 C6 127.59(18) . . ?
N1 C7 H7 116.2 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 111.34(16) . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.13(17) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C11 C10 C9 121.5(2) . . ?
N2 C10 C9 118.12(18) . . ?
N2 C10 C11 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 118.9 . . ?
N2 C14 C13 122.2(2) . . ?
N2 C14 H14 118.9 . . ?
C7 N1 C8 116.70(16) . . ?
C7 N1 Pd1 123.30(14) . . ?
C8 N1 Pd1 120.00(12) . . ?
C10 N2 C14 119.27(18) . . ?
C10 N2 Pd1 121.65(14) . . ?
C14 N2 Pd1 119.06(14) . . ?
C1 O1 Pd1 124.56(13) . . ?
N1 Pd1 Cl1 175.96(5) . . ?
N1 Pd1 N2 92.74(7) . . ?
N2 Pd1 Cl1 91.27(5) . . ?
O1 Pd1 Cl1 84.59(4) . . ?
O1 Pd1 N1 91.40(6) . . ?
O1 Pd1 N2 175.85(6) . . ?
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
Br1 C2 1.892(2) . ?
Br2 C4 1.902(2) . ?
C1 C2 1.422(3) . ?
C1 C6 1.410(3) . ?
C1 O1 1.301(2) . ?
C2 C3 1.376(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 C5 1.369(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.410(3) . ?
C6 C7 1.445(3) . ?
C7 H7 0.9500 . ?
C7 N1 1.283(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.521(3) . ?
C8 N1 1.475(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.496(3) . ?
C10 C11 1.388(3) . ?
C10 N2 1.352(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9500 . ?
C14 N2 1.353(3) . ?
Cl1 Pd1 2.3134(5) . ?
N1 Pd1 2.0044(16) . ?
N2 Pd1 2.0337(17) . ?
O1 Pd1 1.9857(14) . ?
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
Br1 C2 C3 C4 -178.99(16) . . . . ?
Br2 C4 C5 C6 -177.08(15) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C6 C7 N1 12.0(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 177.43(18) . . . . ?
C2 C1 O1 Pd1 160.15(14) . . . . ?
C2 C3 C4 Br2 178.00(16) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 -178.28(19) . . . . ?
C5 C6 C7 N1 -171.2(2) . . . . ?
C6 C1 C2 Br1 178.78(14) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C1 O1 Pd1 -20.6(3) . . . . ?
C6 C7 N1 C8 -178.6(2) . . . . ?
C6 C7 N1 Pd1 2.2(3) . . . . ?
C8 C9 C10 C11 123.3(2) . . . . ?
C8 C9 C10 N2 -55.3(2) . . . . ?
C9 C8 N1 C7 150.68(18) . . . . ?
C9 C8 N1 Pd1 -30.1(2) . . . . ?
C9 C10 C11 C12 -178.7(2) . . . . ?
C9 C10 N2 C14 177.22(18) . . . . ?
C9 C10 N2 Pd1 -4.8(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C10 N2 C14 -1.3(3) . . . . ?
C11 C10 N2 Pd1 176.61(15) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 N2 -0.8(3) . . . . ?
C13 C14 N2 C10 1.9(3) . . . . ?
C13 C14 N2 Pd1 -176.15(16) . . . . ?
N1 C8 C9 C10 74.1(2) . . . . ?
N2 C10 C11 C12 -0.2(3) . . . . ?
O1 C1 C2 Br1 -2.0(3) . . . . ?
O1 C1 C2 C3 179.47(19) . . . . ?
O1 C1 C6 C5 -178.51(19) . . . . ?
O1 C1 C6 C7 -1.8(3) . . . . ?
