#------------------------------------------------------------------------------
#$Date: 2021-11-16 11:55:41 +0200 (Tue, 16 Nov 2021) $
#$Revision: 270685 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/52/1565250.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_1565250
loop_
_publ_author_name
'Sharma, Mitu'
'Ganeshpandian, Mani'
'Sanjeev, Airy'
'Tamilarasan, Ajaykamal'
'Mattaparthi, Venkata Satish Kumar'
'Islam, Nashreen S.'
'Palaniandavar, Mallayan'
_publ_section_title
;
 Bis- and mixed-ligand copper(II) complexes of nalidixic acid the
 antibacterial drug: Mode of nalidixate coordination determines DNA
 binding and cleavage and cytotoxicity
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119450
_journal_paper_doi               10.1016/j.ica.2020.119450
_journal_volume                  504
_journal_year                    2020
_chemical_formula_sum            'C24 H26 Cu N4 O8'
_chemical_formula_weight         562.04
_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   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 99.809(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2910(3)
_cell_length_b                   7.4556(3)
_cell_length_c                   19.2127(6)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.49
_cell_volume                     1170.26(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29336
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.151
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.994
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            BLUE
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0484
_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)+(0.0718P)²+2.7540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1469
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1892
_reflns_number_total             2060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Cunal2CIF.cif
_cod_data_source_block           55
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1565250
_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_min   0.755
_shelx_estimated_absorpt_t_max   0.841
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_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
Cu Cu -0.5000 0.5000 0.5000 0.0350(3) Uani 1 2 d S . P . .
O1 O -0.4879(3) 0.4969(4) 0.40245(14) 0.0409(7) Uani 1 1 d . . . . .
O2 O -0.2974(3) 0.3694(4) 0.52597(13) 0.0398(6) Uani 1 1 d . . . . .
O3 O -0.3935(4) 0.4390(5) 0.30496(15) 0.0531(8) Uani 1 1 d . . . . .
N1 N 0.0558(4) 0.2765(5) 0.40398(16) 0.0411(8) Uani 1 1 d . . . . .
N2 N 0.2375(4) 0.1724(4) 0.50128(18) 0.0397(8) Uani 1 1 d . . . . .
C1 C -0.3755(4) 0.4388(5) 0.36950(19) 0.0337(8) Uani 1 1 d . . . . .
C2 C -0.2192(4) 0.3690(5) 0.41180(19) 0.0315(8) Uani 1 1 d . . . . .
C3 C -0.0917(4) 0.3381(5) 0.37535(19) 0.0373(9) Uani 1 1 d . . . . .
H3 H -0.1103 0.3620 0.3271 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0875(4) 0.2358(5) 0.47563(19) 0.0330(8) Uani 1 1 d . . . . .
C5 C 0.2684(5) 0.1266(5) 0.5695(2) 0.0387(9) Uani 1 1 d . . . . .
C6 C 0.1522(5) 0.1467(5) 0.6141(2) 0.0432(9) Uani 1 1 d . . . . .
H6 H 0.1775 0.1123 0.6612 0.052 Uiso 1 1 calc R U . . .
C7 C 0.0018(5) 0.2169(5) 0.5880(2) 0.0389(9) Uani 1 1 d . . . . .
H7 H -0.0748 0.2338 0.6176 0.047 Uiso 1 1 calc R U . . .
C8 C -0.0362(4) 0.2635(5) 0.51623(19) 0.0320(8) Uani 1 1 d . . . . .
C9 C -0.1940(4) 0.3380(5) 0.48554(18) 0.0309(8) Uani 1 1 d . . . . .
C10 C 0.1842(5) 0.2574(11) 0.3586(3) 0.079(2) Uani 1 1 d . . . . .
H10A H 0.2126 0.3767 0.3446 0.095 Uiso 1 1 calc R U . . .
H10B H 0.2812 0.2074 0.3875 0.095 Uiso 1 1 calc R U . . .
C11 C 0.1491(8) 0.1567(13) 0.2999(4) 0.113(3) Uani 1 1 d . . . . .
H11A H 0.0386 0.1701 0.2756 0.136 Uiso 1 1 d R U . . .
H11B H 0.2233 0.2019 0.2708 0.136 Uiso 1 1 d R U . . .
H11C H 0.1716 0.0321 0.3098 0.136 Uiso 1 1 d R U . . .
C12 C 0.4364(5) 0.0531(6) 0.5966(3) 0.0515(11) Uani 1 1 d . . . . .
H12A H 0.5166 0.1132 0.5744 0.062 Uiso 1 1 d R U . . .
H12B H 0.4612 0.0712 0.6467 0.062 Uiso 1 1 d R U . . .
H12C H 0.4377 -0.0729 0.5864 0.062 Uiso 1 1 d R U . . .
O4A O 0.7249(6) 0.1635(7) 0.2232(3) 0.117(2) Uani 1 1 d . . . . .
H4A H 0.6495 0.1356 0.1849 0.176 Uiso 1 1 d R U . . .
H5A H 0.671(8) 0.221(9) 0.249(3) 0.08(2) 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'
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
O1 Cu O1 180.0 3_466 .
O1 Cu O2 93.38(11) 3_466 3_466
O1 Cu O2 86.62(11) . 3_466
O1 Cu O2 86.62(11) 3_466 .
O1 Cu O2 93.38(11) . .
O2 Cu O2 180.0 3_466 .
C1 O1 Cu 131.0(2) . .
C9 O2 Cu 125.6(2) . .
C3 N1 C4 119.3(3) . .
C3 N1 C10 119.1(4) . .
C4 N1 C10 121.6(3) . .
C5 N2 C4 117.4(3) . .
O3 C1 O1 121.6(3) . .
O3 C1 C2 119.6(3) . .
O1 C1 C2 118.7(3) . .
C3 C2 C9 119.0(3) . .
C3 C2 C1 116.6(3) . .
C9 C2 C1 124.4(3) . .
N1 C3 C2 125.1(3) . .
N1 C3 H3 117.5 . .
C2 C3 H3 117.5 . .
N2 C4 N1 116.6(3) . .
N2 C4 C8 124.4(3) . .
N1 C4 C8 119.0(3) . .
N2 C5 C6 122.4(3) . .
N2 C5 C12 116.4(4) . .
C6 C5 C12 121.2(4) . .
C7 C6 C5 119.7(4) . .
C7 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C6 C7 C8 119.5(4) . .
C6 C7 H7 120.3 . .
C8 C7 H7 120.3 . .
C7 C8 C4 116.5(3) . .
C7 C8 C9 122.0(3) . .
C4 C8 C9 121.6(3) . .
O2 C9 C2 125.5(3) . .
O2 C9 C8 118.5(3) . .
C2 C9 C8 116.0(3) . .
C11 C10 N1 118.0(5) . .
C11 C10 H10A 107.8 . .
N1 C10 H10A 107.8 . .
C11 C10 H10B 107.8 . .
N1 C10 H10B 107.8 . .
H10A C10 H10B 107.2 . .
C10 C11 H11A 113.7 . .
C10 C11 H11B 103.0 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 111.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C5 C12 H12A 110.3 . .
C5 C12 H12B 108.9 . .
H12A C12 H12B 109.5 . .
C5 C12 H12C 109.2 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
H4A O4A H5A 103.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu O1 1.894(3) 3_466
Cu O1 1.894(3) .
Cu O2 1.932(2) 3_466
Cu O2 1.932(2) .
O1 C1 1.287(4) .
O2 C9 1.273(4) .
O3 C1 1.224(5) .
N1 C3 1.334(5) .
N1 C4 1.390(5) .
N1 C10 1.494(5) .
N2 C5 1.336(5) .
N2 C4 1.343(5) .
C1 C2 1.501(5) .
C2 C3 1.383(5) .
C2 C9 1.415(5) .
C3 H3 0.9300 .
C4 C8 1.405(5) .
C5 C6 1.402(6) .
C5 C12 1.505(5) .
C6 C7 1.367(5) .
C6 H6 0.9300 .
C7 C8 1.405(5) .
C7 H7 0.9300 .
C8 C9 1.451(5) .
C10 C11 1.345(8) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9601 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
O4A H4A 0.9047 .
O4A H5A 0.84(6) .
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
O4A H4A O3 0.90 2.61 3.184(6) 121.8 2_545
O4A H4A O1 0.90 2.22 3.101(5) 165.4 2_545
C11 H11A O4A 0.96 2.62 3.575(8) 170.4 1_455
C10 H10A O4A 0.97 2.60 3.551(9) 166.3 2_655
C3 H3 O4A 0.93 2.67 3.322(6) 128.0 1_455
O4A H4A O3 0.90 2.61 3.184(6) 121.8 2_545
O4A H4A O1 0.90 2.22 3.101(5) 165.4 2_545
C11 H11A O4A 0.96 2.62 3.575(8) 170.4 1_455
C10 H10B N2 0.97 2.29 2.774(6) 109.9 .
C10 H10A O4A 0.97 2.60 3.551(9) 166.3 2_655
C3 H3 O4A 0.93 2.67 3.322(6) 128.0 1_455
C3 H3 O4A 0.93 2.67 3.322(6) 128.0 1_455
C10 H10A O4A 0.97 2.60 3.551(9) 166.3 2_655
C11 H11A O4A 0.96 2.62 3.575(8) 170.4 1_455
O4A H4A O1 0.90 2.22 3.101(5) 165.4 2_545
O4A H4A O3 0.90 2.61 3.184(6) 121.8 2_545
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
O2 Cu O1 C1 175.4(3) 3_466 . . .
O2 Cu O1 C1 -4.6(3) . . . .
Cu O1 C1 O3 175.8(3) . . . .
Cu O1 C1 C2 -4.1(5) . . . .
O3 C1 C2 C3 11.3(5) . . . .
O1 C1 C2 C3 -168.9(3) . . . .
O3 C1 C2 C9 -170.4(4) . . . .
O1 C1 C2 C9 9.5(5) . . . .
C4 N1 C3 C2 1.2(6) . . . .
C10 N1 C3 C2 -177.3(4) . . . .
C9 C2 C3 N1 1.5(6) . . . .
C1 C2 C3 N1 179.9(4) . . . .
C5 N2 C4 N1 -177.7(3) . . . .
C5 N2 C4 C8 2.6(6) . . . .
C3 N1 C4 N2 179.3(4) . . . .
C10 N1 C4 N2 -2.3(6) . . . .
C3 N1 C4 C8 -1.1(5) . . . .
C10 N1 C4 C8 177.4(4) . . . .
C4 N2 C5 C6 -1.6(6) . . . .
C4 N2 C5 C12 179.0(3) . . . .
N2 C5 C6 C7 -0.6(6) . . . .
C12 C5 C6 C7 178.8(4) . . . .
C5 C6 C7 C8 1.8(6) . . . .
C6 C7 C8 C4 -0.8(5) . . . .
C6 C7 C8 C9 179.8(4) . . . .
N2 C4 C8 C7 -1.5(5) . . . .
N1 C4 C8 C7 178.9(3) . . . .
N2 C4 C8 C9 177.9(3) . . . .
N1 C4 C8 C9 -1.7(5) . . . .
Cu O2 C9 C2 -10.0(5) . . . .
Cu O2 C9 C8 170.2(2) . . . .
C3 C2 C9 O2 176.2(4) . . . .
C1 C2 C9 O2 -2.1(6) . . . .
C3 C2 C9 C8 -4.0(5) . . . .
C1 C2 C9 C8 177.7(3) . . . .
C7 C8 C9 O2 3.4(5) . . . .
C4 C8 C9 O2 -176.0(3) . . . .
C7 C8 C9 C2 -176.4(3) . . . .
C4 C8 C9 C2 4.2(5) . . . .
C3 N1 C10 C11 -55.7(9) . . . .
C4 N1 C10 C11 125.8(7) . . . .
