#------------------------------------------------------------------------------
#$Date: 2022-02-17 01:54:33 +0200 (Thu, 17 Feb 2022) $
#$Revision: 272994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/95/7709548.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_7709548
loop_
_publ_author_name
'Chen, Yating'
'Zhang, Shaonan'
'Wang, Zhen-Feng'
'Wei, Qingmin'
'Zhang, Shuhua'
_publ_section_title
;
 Discovery of thirteen cobalt (II) and copper (II) salicylaldehyde Schiff
 base complexes that induce apoptosis and autophagy in human lung
 adenocarcinoma A549/DDP cells and that can overcome cisplatin resistance
 in vitro and in vivo
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03749H
_journal_year                    2022
_chemical_formula_moiety         'C24 H18 Br2 Cl2 Cu N6 O2, N O3, 2(H2 O)'
_chemical_formula_sum            'C24 H22 Br2 Cl2 Cu N7 O7'
_chemical_formula_weight         814.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2021-12-07 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.478(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.6667(10)
_cell_length_b                   7.2097(4)
_cell_length_c                   21.1442(13)
_cell_measurement_reflns_used    3081
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0120
_cell_measurement_theta_min      3.7200
_cell_volume                     3119.4(3)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0233
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10066
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.097
_diffrn_reflns_theta_min         3.356
_exptl_absorpt_coefficient_mu    3.487
_exptl_absorpt_correction_T_max  0.659
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            BLUE
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.615(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5079
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0439
_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)+(0.0459P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3710
_reflns_number_total             5079
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt03749h2.cif
_cod_data_source_block           CU
_cod_original_cell_volume        3119.3(3)
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               7709548
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-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
Cu1 Cu 0.99499(4) 0.24954(14) 0.17055(5) 0.0507(3) Uani 1 1 d . . . . .
Br1 Br 1.15604(4) 0.70298(16) 0.33215(6) 0.0851(4) Uani 1 1 d . . . . .
Br2 Br 0.77465(5) -0.05262(18) 0.12405(6) 0.0858(4) Uani 1 1 d . . . . .
N6 N 1.0918(3) 0.2772(9) 0.1958(4) 0.0466(17) Uani 1 1 d . . . . .
C11 C 1.0691(4) 0.6852(13) 0.3232(5) 0.057(2) Uani 1 1 d . . . . .
N3 N 0.9165(3) 0.4283(10) 0.1484(3) 0.0451(16) Uani 1 1 d . . . . .
C16 C 1.1983(3) 0.2271(14) 0.2906(5) 0.060(2) Uani 1 1 d . . . . .
H16 H 1.2236 0.1942 0.3371 0.072 Uiso 1 1 calc R U . . .
N1 N 0.9283(3) 0.1247(10) 0.0846(3) 0.0477(17) Uani 1 1 d . . . . .
C12 C 1.0202(4) 0.6277(11) 0.2602(4) 0.046(2) Uani 1 1 d . . . . .
H12 H 1.0296 0.6013 0.2225 0.055 Uiso 1 1 calc R U . . .
N2 N 0.8656(3) 0.3729(11) 0.0874(3) 0.056(2) Uani 1 1 d . . . . .
H2 H 0.8302 0.4370 0.0698 0.067 Uiso 1 1 calc R U . . .
C5 C 0.8713(3) 0.2172(13) 0.0551(4) 0.046(2) Uani 1 1 d . . . . .
N4 N 1.0320(3) 0.1746(10) 0.2752(3) 0.0440(17) Uani 1 1 d . . . . .
C20 C 0.8952(4) 0.0713(12) 0.2316(5) 0.052(2) Uani 1 1 d . . . . .
H20 H 0.9119 0.0368 0.2001 0.062 Uiso 1 1 calc R U . . .
C7 C 0.9559(4) 0.6092(11) 0.2533(4) 0.0434(19) Uani 1 1 d . . . . .
N5 N 1.1000(3) 0.1827(11) 0.3033(4) 0.0559(19) Uani 1 1 d . . . . .
H5 H 1.1230 0.1581 0.3469 0.067 Uiso 1 1 calc R U . . .
C21 C 0.8287(4) 0.0522(13) 0.2129(5) 0.053(2) Uani 1 1 d . . . . .
C8 C 0.9425(4) 0.6594(11) 0.3097(4) 0.048(2) Uani 1 1 d . . . . .
C1 C 0.9313(4) -0.0340(15) 0.0540(5) 0.060(2) Uani 1 1 d . . . . .
C18 C 1.0068(4) 0.1594(12) 0.3174(5) 0.052(2) Uani 1 1 d . . . . .
H18 H 1.0345 0.1597 0.3650 0.062 Uiso 1 1 calc R U . . .
C10 C 1.0555(4) 0.7289(14) 0.3789(5) 0.065(3) Uani 1 1 d . . . . .
H10 H 1.0891 0.7672 0.4210 0.078 Uiso 1 1 calc R U . . .
O1 O 0.8796(3) 0.6469(9) 0.3015(3) 0.0655(17) Uani 1 1 d . . . . .
C9 C 0.9933(4) 0.7166(14) 0.3730(4) 0.062(2) Uani 1 1 d . . . . .
H9 H 0.9847 0.7461 0.4110 0.075 Uiso 1 1 calc R U . . .
C17 C 1.1297(3) 0.2291(13) 0.2625(4) 0.048(2) Uani 1 1 d . . . . .
C14 C 1.1881(5) 0.3283(15) 0.1791(6) 0.072(3) Uani 1 1 d . . . . .
H14 H 1.2071 0.3644 0.1499 0.086 Uiso 1 1 calc R U . . .
C15 C 1.2261(4) 0.2747(15) 0.2479(6) 0.071(3) Uani 1 1 d . . . . .
H15 H 1.2714 0.2716 0.2648 0.085 Uiso 1 1 calc R U . . .
C13 C 1.1216(4) 0.3262(13) 0.1559(5) 0.054(2) Uani 1 1 d . . . . .
C6 C 0.9049(4) 0.5420(12) 0.1883(4) 0.050(2) Uani 1 1 d . . . . .
H6 H 0.8622 0.5825 0.1750 0.060 Uiso 1 1 calc R U . . .
O2 O 0.9536(3) 0.2604(12) 0.4072(3) 0.080(2) Uani 1 1 d . . . . .
H2A H 0.9346 0.3367 0.4204 0.120 Uiso 1 1 calc DR U . . .
C22 C 0.8042(4) 0.1014(15) 0.2593(6) 0.071(3) Uani 1 1 d . . . . .
H22 H 0.7599 0.0865 0.2471 0.085 Uiso 1 1 calc R U . . .
C19 C 0.9367(4) 0.1413(12) 0.2966(5) 0.050(2) Uani 1 1 d . . . . .
C24 C 0.9109(4) 0.1907(14) 0.3425(5) 0.062(2) Uani 1 1 d . . . . .
Cl2 Cl 1.07100(12) 0.3873(4) 0.07077(14) 0.0803(8) Uani 1 1 d . . . . .
Cl1 Cl 1.00592(15) -0.1492(4) 0.09398(16) 0.0910(9) Uani 1 1 d . . . . .
C3 C 0.8244(6) -0.0073(18) -0.0352(6) 0.080(3) Uani 1 1 d . . . . .
H3 H 0.7898 -0.0522 -0.0752 0.096 Uiso 1 1 calc R U . . .
C2 C 0.8823(6) -0.1048(16) -0.0047(5) 0.079(3) Uani 1 1 d . . . . .
H2B H 0.8877 -0.2161 -0.0238 0.095 Uiso 1 1 calc R U . . .
C23 C 0.8449(5) 0.1736(17) 0.3244(6) 0.076(3) Uani 1 1 d . . . . .
H23 H 0.8279 0.2098 0.3555 0.092 Uiso 1 1 calc R U . . .
C4 C 0.8188(4) 0.1540(16) -0.0060(5) 0.067(3) Uani 1 1 d . . . . .
H4 H 0.7805 0.2229 -0.0262 0.080 Uiso 1 1 calc R U . . .
O4 O 0.8699(5) 0.7463(15) 0.4218(5) 0.107(3) Uani 1 1 d G . . . .
H4A H 0.8689 0.6303 0.4286 0.160 Uiso 1 1 d G U . . .
H4B H 0.8410 0.8001 0.4309 0.160 Uiso 1 1 d G U . . .
O3 O 0.9068(3) 0.3860(12) 0.4966(2) 0.093(2) Uani 1 1 d G . . . .
N7 N 0.7118(2) 0.5753(7) -0.0133(2) 0.086(3) Uani 1 1 d G U . . .
O6 O 0.7252(2) 0.4962(7) 0.0444(2) 0.113(3) Uani 1 1 d G . . . .
O7 O 0.7501(2) 0.5777(12) -0.0397(2) 0.113(3) Uani 1 1 d G . . . .
O5 O 0.6587(3) 0.6515(11) -0.0464(2) 0.133(3) Uani 1 1 d G U . . .
H1 H 0.8652 0.6895 0.3222 0.199 Uiso 1 1 d G U . . .
H3B H 0.8881 0.2810 0.4907 0.199 Uiso 1 1 d DR U . . .
H3A H 0.9409 0.3770 0.5352 0.199 Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
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 Cu1 N6 126.1(3) . . ?
N1 Cu1 N4 130.6(3) . . ?
N6 Cu1 N4 81.3(3) . . ?
N1 Cu1 N3 80.5(3) . . ?
N6 Cu1 N3 136.1(3) . . ?
N4 Cu1 N3 108.4(2) . . ?
C13 N6 C17 117.6(6) . . ?
C13 N6 Cu1 130.0(6) . . ?
C17 N6 Cu1 112.3(5) . . ?
C10 C11 C12 120.7(8) . . ?
C10 C11 Br1 120.2(7) . . ?
C12 C11 Br1 119.0(7) . . ?
C6 N3 N2 118.5(6) . . ?
C6 N3 Cu1 130.2(5) . . ?
N2 N3 Cu1 108.9(5) . . ?
C15 C16 C17 117.7(9) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C5 N1 C1 116.2(7) . . ?
C5 N1 Cu1 113.4(6) . . ?
C1 N1 Cu1 130.4(6) . . ?
C11 C12 C7 119.7(8) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C5 N2 N3 119.6(7) . . ?
C5 N2 H2 120.2 . . ?
N3 N2 H2 120.2 . . ?
N1 C5 N2 117.4(7) . . ?
N1 C5 C4 122.1(9) . . ?
N2 C5 C4 120.5(8) . . ?
C18 N4 N5 117.3(7) . . ?
C18 N4 Cu1 133.0(5) . . ?
N5 N4 Cu1 108.1(5) . . ?
C19 C20 C21 120.5(9) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C8 C7 C12 118.8(7) . . ?
C8 C7 C6 121.3(7) . . ?
C12 C7 C6 119.9(7) . . ?
C17 N5 N4 120.2(6) . . ?
C17 N5 H5 119.9 . . ?
N4 N5 H5 119.9 . . ?
C22 C21 C20 119.8(9) . . ?
C22 C21 Br2 121.7(7) . . ?
C20 C21 Br2 118.5(7) . . ?
O1 C8 C7 118.2(7) . . ?
O1 C8 C9 121.8(8) . . ?
C7 C8 C9 120.0(8) . . ?
N1 C1 C2 125.0(9) . . ?
N1 C1 Cl1 114.7(7) . . ?
C2 C1 Cl1 120.3(8) . . ?
N4 C18 C19 124.3(8) . . ?
N4 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?
C11 C10 C9 120.7(8) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C8 O1 H1 128.2 . . ?
C10 C9 C8 120.0(9) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N5 C17 N6 117.8(6) . . ?
N5 C17 C16 119.6(8) . . ?
N6 C17 C16 122.5(8) . . ?
C13 C14 C15 117.6(9) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C16 C15 C14 120.8(8) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C14 C13 N6 123.7(9) . . ?
C14 C13 Cl2 120.3(8) . . ?
N6 C13 Cl2 116.0(6) . . ?
N3 C6 C7 122.2(7) . . ?
N3 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C24 O2 H2A 109.5 . . ?
C23 C22 C21 120.6(8) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C19 C20 118.7(8) . . ?
C24 C19 C18 120.1(9) . . ?
C20 C19 C18 121.2(8) . . ?
C19 C24 C23 121.4(10) . . ?
C19 C24 O2 117.4(8) . . ?
C23 C24 O2 121.2(9) . . ?
C2 C3 C4 118.9(10) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C1 C2 C3 118.3(10) . . ?
C1 C2 H2B 120.8 . . ?
C3 C2 H2B 120.8 . . ?
C22 C23 C24 119.0(9) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C3 C4 C5 119.5(10) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
H4A O4 H4B 109.5 . . ?
H3B O3 H3A 105.2 . . ?
O7 N7 O5 116.6 . . ?
O7 N7 O6 121.9 . . ?
O5 N7 O6 121.5 . . ?
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
Cu1 N1 2.009(7) . ?
Cu1 N6 2.034(6) . ?
Cu1 N4 2.071(7) . ?
Cu1 N3 2.081(6) . ?
Br1 C11 1.901(8) . ?
Br2 C21 1.903(9) . ?
N6 C13 1.333(10) . ?
N6 C17 1.344(10) . ?
C11 C10 1.376(12) . ?
C11 C12 1.380(11) . ?
N3 C6 1.282(10) . ?
N3 N2 1.369(8) . ?
C16 C15 1.350(12) . ?
C16 C17 1.404(10) . ?
C16 H16 0.9300 . ?
N1 C5 1.344(10) . ?
N1 C1 1.331(12) . ?
C12 C7 1.407(11) . ?
C12 H12 0.9300 . ?
N2 C5 1.350(11) . ?
N2 H2 0.8600 . ?
C5 C4 1.403(11) . ?
N4 C18 1.256(10) . ?
N4 N5 1.393(8) . ?
C20 C19 1.385(12) . ?
C20 C21 1.392(11) . ?
C20 H20 0.9300 . ?
C7 C8 1.398(11) . ?
C7 C6 1.447(11) . ?
N5 C17 1.346(10) . ?
N5 H5 0.8600 . ?
C21 C22 1.365(13) . ?
C8 O1 1.363(9) . ?
C8 C9 1.400(11) . ?
C1 C2 1.360(13) . ?
C1 Cl1 1.742(9) . ?
C18 C19 1.460(11) . ?
C18 H18 0.9300 . ?
C10 C9 1.363(11) . ?
C10 H10 0.9300 . ?
O1 H1 0.7180 . ?
C9 H9 0.9300 . ?
C14 C13 1.370(11) . ?
C14 C15 1.389(13) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C13 Cl2 1.725(9) . ?
C6 H6 0.9300 . ?
O2 C24 1.387(11) . ?
O2 H2A 0.8200 . ?
C22 C23 1.387(14) . ?
C22 H22 0.9300 . ?
C19 C24 1.377(12) . ?
C24 C23 1.382(12) . ?
C3 C2 1.380(14) . ?
C3 C4 1.348(15) . ?
C3 H3 0.9300 . ?
C2 H2B 0.9300 . ?
C23 H23 0.9300 . ?
C4 H4 0.9300 . ?
O4 H4A 0.8501 . ?
O4 H4B 0.8497 . ?
O3 H3B 0.8501 . ?
O3 H3A 0.8507 . ?
N7 O7 1.2192 . ?
N7 O5 1.2304 . ?
N7 O6 1.2604 . ?
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
N2 H2 O6 0.86 2.24 3.043(8) 154.5 .
N2 H2 O7 0.86 2.46 3.195(9) 143.2 .
N5 H5 O5 0.86 2.04 2.877(9) 163.3 3_545
O2 H2A O3 0.82 2.00 2.692(9) 142.2 .
O4 H4A O3 0.85 2.20 2.968(12) 150.0 .
O4 H4B O6 0.85 2.28 3.12(3) 168.7 4_655
O1 H1 O4 0.72 2.10 2.742(10) 148.7 .
O3 H3B O5 0.85 2.11 2.742(17) 130.6 4_645
O3 H3A O2 0.85 2.32 3.070(9) 146.5 2_756
