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#$Date: 2021-06-05 22:20:36 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060585.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_7060585
loop_
_publ_author_name
'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'
_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_sum            'C25 H32 N3 O7 Zn'
_chemical_formula_weight         551.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc24sbw5
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-03-11 deposited with the CCDC.	2021-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                66.842(2)
_cell_angle_beta                 80.572(2)
_cell_angle_gamma                73.764(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3339(3)
_cell_length_b                   12.2926(5)
_cell_length_c                   14.6424(6)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.5
_cell_volume                     1321.71(9)
_computing_cell_refinement       'SMART APEX II'
_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22930
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.515
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         6035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0501
_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)+(0.0605P)²+1.4506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4500
_reflns_number_total             6035
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj01491a2.cif
_cod_data_source_block           DG1b
_cod_depositor_comments
'Adding full bibliography for 7060575--7060596.cif.'
_cod_database_code               7060585
_shelx_shelxl_version_number     2017/1
_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.
;
_exptl_absorpt_special_details
;
 ?
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.8074(4) 0.2123(3) 0.1887(3) 0.0414(8) Uani 1 1 d . . . . .
H1 H 0.831459 0.151446 0.250696 0.050 Uiso 1 1 calc R U . . .
C2 C 0.9238(4) 0.2784(3) 0.1384(3) 0.0452(9) Uani 1 1 d . . . . .
H2 H 1.022926 0.263460 0.167429 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8952(4) 0.3666(3) 0.0454(3) 0.0383(8) Uani 1 1 d . . . . .
C4 C 0.7443(5) 0.3856(3) 0.0073(3) 0.0400(8) Uani 1 1 d . . . . .
H4 H 0.719582 0.443794 -0.055636 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6308(4) 0.3187(3) 0.0623(2) 0.0353(7) Uani 1 1 d . . . . .
H5 H 0.528931 0.334272 0.035836 0.042 Uiso 1 1 calc R U . . .
C6 C 1.0190(5) 0.4421(3) -0.0105(3) 0.0462(9) Uani 1 1 d . . . . .
H6A H 1.015510 0.462357 -0.081317 0.055 Uiso 1 1 calc R U . . .
H6B H 1.131006 0.395170 0.008788 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2468(4) 0.0180(3) 0.2169(3) 0.0365(8) Uani 1 1 d . . . . .
H7 H 0.238158 -0.002987 0.285548 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1524(4) -0.0251(3) 0.1767(3) 0.0413(8) Uani 1 1 d . . . . .
H8 H 0.079312 -0.071879 0.217523 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1661(4) 0.0010(3) 0.0755(3) 0.0365(8) Uani 1 1 d . . . . .
C10 C 0.2705(5) 0.0773(4) 0.0192(3) 0.0452(9) Uani 1 1 d . . . . .
H10 H 0.280007 0.100952 -0.049691 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3594(5) 0.1176(4) 0.0648(3) 0.0426(9) Uani 1 1 d . . . . .
H11 H 0.429542 0.167763 0.025490 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0723(5) -0.0487(3) 0.0273(3) 0.0418(8) Uani 1 1 d . . . . .
H12A H 0.030398 -0.115462 0.077833 0.050 Uiso 1 1 calc R U . . .
H12B H 0.148055 -0.080274 -0.019188 0.050 Uiso 1 1 calc R U . . .
C22 C 0.4744(6) 0.7070(4) 0.2016(3) 0.0698(14) Uani 1 1 d . . . . .
H22 H 0.442074 0.789891 0.164559 0.084 Uiso 1 1 calc R U . . .
C21 C 0.4313(6) 0.6694(4) 0.3025(3) 0.0659(13) Uani 1 1 d . . . . .
H21 H 0.369843 0.724991 0.331092 0.079 Uiso 1 1 calc R U . . .
C20 C 0.4812(5) 0.5477(4) 0.3597(3) 0.0502(10) Uani 1 1 d . . . . .
C24 C 0.5732(7) 0.4742(4) 0.3107(3) 0.0668(13) Uani 1 1 d . . . . .
H24 H 0.614935 0.391844 0.346366 0.080 Uiso 1 1 calc R U . . .
C23 C 0.6048(7) 0.5201(5) 0.2101(3) 0.0699(14) Uani 1 1 d . . . . .
H23 H 0.663904 0.466323 0.179156 0.084 Uiso 1 1 calc R U . . .
C25 C 0.4369(6) 0.4985(5) 0.4707(3) 0.0686(14) Uani 1 1 d . . . . .
H25A H 0.328835 0.546395 0.484997 0.082 Uiso 1 1 calc R U . . .
H25B H 0.427629 0.415176 0.490822 0.082 Uiso 1 1 calc R U . . .
C13 C 0.2740(4) 0.3079(3) 0.2823(3) 0.0315(7) Uani 1 1 d . . . . .
C14 C 0.1694(5) 0.3758(3) 0.3461(3) 0.0418(9) Uani 1 1 d . . . . .
H14A H 0.240847 0.376841 0.391685 0.050 Uiso 1 1 calc R U . . .
H14B H 0.085835 0.332098 0.385614 0.050 Uiso 1 1 calc R U . . .
C15 C 0.0818(5) 0.5054(3) 0.2877(3) 0.0432(9) Uani 1 1 d . . . . .
H15A H 0.006847 0.504018 0.244204 0.052 Uiso 1 1 calc R U . . .
H15B H 0.165130 0.547907 0.245850 0.052 Uiso 1 1 calc R U . . .
C16 C -0.0175(5) 0.5765(3) 0.3508(3) 0.0413(9) Uani 1 1 d . . . . .
H16A H 0.057238 0.580220 0.393269 0.050 Uiso 1 1 calc R U . . .
H16B H -0.100344 0.534156 0.393395 0.050 Uiso 1 1 calc R U . . .
C17 C -0.1048(5) 0.7046(3) 0.2885(3) 0.0415(9) Uani 1 1 d . . . . .
H17A H -0.021211 0.745806 0.245557 0.050 Uiso 1 1 calc R U . . .
H17B H -0.178842 0.699965 0.246171 0.050 Uiso 1 1 calc R U . . .
C18 C -0.2053(5) 0.7803(3) 0.3474(3) 0.0407(8) Uani 1 1 d . . . . .
H18A H -0.288955 0.739131 0.390387 0.049 Uiso 1 1 calc R U . . .
H18B H -0.131374 0.785199 0.389581 0.049 Uiso 1 1 calc R U . . .
C19 C -0.2922(4) 0.9077(3) 0.2846(2) 0.0313(7) Uani 1 1 d . . . . .
N1 N 0.6607(3) 0.2320(2) 0.1522(2) 0.0305(6) Uani 1 1 d . . . . .
N2 N 0.3501(3) 0.0881(2) 0.1630(2) 0.0300(6) Uani 1 1 d . . . . .
N3 N 0.5563(5) 0.6364(4) 0.1540(3) 0.0631(10) Uani 1 1 d . . . . .
O1 O 0.3673(3) 0.2023(2) 0.33035(17) 0.0412(6) Uani 1 1 d . . . . .
O2 O 0.2713(3) 0.3479(2) 0.19217(18) 0.0461(6) Uani 1 1 d . . . . .
O3WA O 0.1597(9) 0.0636(7) 0.4817(6) 0.083(2) Uani 0.5 1 d G . P . .
O3 O -0.3940(3) 0.9707(2) 0.33151(17) 0.0391(6) Uani 1 1 d . . . . .
O2W O 0.5673(5) 0.1413(4) 0.4911(3) 0.0753(11) Uani 1 1 d . . . . .
O4 O -0.2663(3) 0.9490(2) 0.19455(18) 0.0475(7) Uani 1 1 d . . . . .
O1W O 0.1630(8) 0.7918(7) 0.4648(7) 0.166(2) Uani 1 1 d G . . . .
H1WA H 0.069263 0.831539 0.481067 0.248 Uiso 1 1 d G U . . .
H1WB H 0.241440 0.804959 0.486488 0.248 Uiso 1 1 d G U . . .
Zn1 Zn 0.49786(4) 0.12996(3) 0.23492(3) 0.02728(12) Uani 1 1 d . . . . .
O3WB O 0.0898(14) 0.0142(10) 0.5763(10) 0.139(4) Uani 0.5 1 d . . P . .
H2WA H 0.518(7) 0.159(5) 0.453(4) 0.07(2) Uiso 1 1 d . . . . .
H2WB H 0.496(9) 0.108(7) 0.555(6) 0.16(3) Uiso 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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.cgd.0c00880 2020
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 C1 C2 122.5(3) . . ?
C1 C2 C3 120.5(3) . . ?
C2 C3 C4 116.8(3) . . ?
C2 C3 C6 121.6(3) . . ?
C4 C3 C6 121.6(3) . . ?
C5 C4 C3 120.1(3) . . ?
N1 C5 C4 122.7(3) . . ?
C3 C6 C6 111.2(4) . 2_765 ?
N2 C7 C8 123.5(3) . . ?
C7 C8 C9 119.8(3) . . ?
C8 C9 C10 116.4(3) . . ?
C8 C9 C12 122.4(3) . . ?
C10 C9 C12 121.2(3) . . ?
C11 C10 C9 120.2(3) . . ?
N2 C11 C10 122.9(3) . . ?
C9 C12 C12 111.0(4) . 2 ?
N3 C22 C21 125.6(4) . . ?
C20 C21 C22 118.5(4) . . ?
C24 C20 C21 116.1(4) . . ?
C24 C20 C25 122.1(4) . . ?
C21 C20 C25 121.9(4) . . ?
C20 C24 C23 120.8(4) . . ?
N3 C23 C24 123.8(4) . . ?
C25 C25 C20 112.3(5) 2_666 . ?
O2 C13 O1 121.8(3) . . ?
O2 C13 C14 122.9(3) . . ?
O1 C13 C14 115.3(3) . . ?
C13 C14 C15 113.9(3) . . ?
C14 C15 C16 114.5(3) . . ?
C15 C16 C17 112.2(3) . . ?
C18 C17 C16 114.7(3) . . ?
C19 C18 C17 114.3(3) . . ?
O4 C19 O3 121.8(3) . . ?
O4 C19 C18 121.9(3) . . ?
O3 C19 C18 116.3(3) . . ?
C1 N1 C5 117.4(3) . . ?
C1 N1 Zn1 118.7(2) . . ?
C5 N1 Zn1 123.9(2) . . ?
C7 N2 C11 117.1(3) . . ?
C7 N2 Zn1 118.4(2) . . ?
C11 N2 Zn1 124.2(2) . . ?
C22 N3 C23 115.2(4) . . ?
C13 O1 Zn1 109.3(2) . . ?
C19 O3 Zn1 109.4(2) . 1_465 ?
O1 Zn1 O3 98.18(9) . 1_645 ?
O1 Zn1 N2 111.90(11) . . ?
O3 Zn1 N2 103.96(10) 1_645 . ?
O1 Zn1 N1 109.15(11) . . ?
O3 Zn1 N1 113.71(10) 1_645 . ?
N2 Zn1 N1 118.12(11) . . ?
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
C1 N1 1.337(4) . ?
C1 C2 1.371(5) . ?
C2 C3 1.374(5) . ?
C3 C4 1.382(5) . ?
C3 C6 1.502(5) . ?
C4 C5 1.372(5) . ?
C5 N1 1.337(4) . ?
C6 C6 1.511(7) 2_765 ?
C7 N2 1.329(4) . ?
C7 C8 1.370(5) . ?
C8 C9 1.380(5) . ?
C9 C10 1.389(5) . ?
C9 C12 1.507(5) . ?
C10 C11 1.366(5) . ?
C11 N2 1.333(4) . ?
C12 C12 1.511(7) 2 ?
C22 N3 1.302(6) . ?
C22 C21 1.380(6) . ?
C21 C20 1.376(6) . ?
C20 C24 1.363(6) . ?
C20 C25 1.516(5) . ?
C24 C23 1.364(6) . ?
C23 N3 1.320(6) . ?
C25 C25 1.478(9) 2_666 ?
C13 O2 1.215(4) . ?
C13 O1 1.297(4) . ?
C13 C14 1.507(4) . ?
C14 C15 1.512(5) . ?
C15 C16 1.511(5) . ?
C16 C17 1.513(4) . ?
C17 C18 1.506(5) . ?
C18 C19 1.508(4) . ?
C19 O4 1.219(4) . ?
C19 O3 1.285(4) . ?
N1 Zn1 2.025(3) . ?
N2 Zn1 2.023(3) . ?
O1 Zn1 1.966(2) . ?
O3WA O3WB 1.378(13) . ?
O3 Zn1 1.974(2) 1_465 ?
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
N1 C1 C2 C3 -2.0(6) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C1 C2 C3 C6 178.7(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C6 C3 C4 C5 -177.1(3) . . . . ?
C3 C4 C5 N1 -1.5(5) . . . . ?
C2 C3 C6 C6 -91.5(5) . . . 2_765 ?
C4 C3 C6 C6 86.0(5) . . . 2_765 ?
N2 C7 C8 C9 2.0(6) . . . . ?
C7 C8 C9 C10 -3.7(5) . . . . ?
C7 C8 C9 C12 176.9(3) . . . . ?
C8 C9 C10 C11 3.1(6) . . . . ?
C12 C9 C10 C11 -177.4(4) . . . . ?
C9 C10 C11 N2 -0.8(6) . . . . ?
C8 C9 C12 C12 105.5(5) . . . 2 ?
C10 C9 C12 C12 -73.9(5) . . . 2 ?
N3 C22 C21 C20 1.7(9) . . . . ?
C22 C21 C20 C24 1.1(7) . . . . ?
C22 C21 C20 C25 -179.1(5) . . . . ?
C21 C20 C24 C23 -3.2(7) . . . . ?
C25 C20 C24 C23 177.0(5) . . . . ?
C20 C24 C23 N3 2.7(9) . . . . ?
C24 C20 C25 C25 90.9(7) . . . 2_666 ?
C21 C20 C25 C25 -88.9(7) . . . 2_666 ?
O2 C13 C14 C15 -9.0(5) . . . . ?
O1 C13 C14 C15 171.5(3) . . . . ?
C13 C14 C15 C16 -177.5(3) . . . . ?
C14 C15 C16 C17 -178.9(3) . . . . ?
C15 C16 C17 C18 -179.7(3) . . . . ?
C16 C17 C18 C19 -179.9(3) . . . . ?
C17 C18 C19 O4 -8.0(5) . . . . ?
C17 C18 C19 O3 172.5(3) . . . . ?
C2 C1 N1 C5 1.1(5) . . . . ?
C2 C1 N1 Zn1 -179.0(3) . . . . ?
C4 C5 N1 C1 0.6(5) . . . . ?
C4 C5 N1 Zn1 -179.3(3) . . . . ?
C8 C7 N2 C11 0.4(5) . . . . ?
C8 C7 N2 Zn1 -173.9(3) . . . . ?
C10 C11 N2 C7 -1.1(5) . . . . ?
C10 C11 N2 Zn1 172.9(3) . . . . ?
C21 C22 N3 C23 -2.3(8) . . . . ?
C24 C23 N3 C22 0.1(8) . . . . ?
O2 C13 O1 Zn1 1.9(4) . . . . ?
C14 C13 O1 Zn1 -178.6(2) . . . . ?
O4 C19 O3 Zn1 3.6(4) . . . 1_465 ?
C18 C19 O3 Zn1 -176.9(2) . . . 1_465 ?
