#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:05:42 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262647 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/64/7706449.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_7706449
loop_
_publ_author_name
'Andrejević, Tina P'
'Aleksic, Ivana'
'Počkaj, Marta'
'Kljun, Jakob'
'Milivojevic, Dusan'
'Stevanović, Nevena Lj'
'Nikodinovic-Runic, Jasmina'
'Turel, Iztok'
'Djuran, Miloš I'
'Glišić, Biljana Đ'
_publ_section_title
;
 Tailoring copper(ii) complexes with pyridine-4,5-dicarboxylate esters for
 anti-Candida activity.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2627
_journal_page_last               2638
_journal_paper_doi               10.1039/d0dt04061d
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C24 H20 Cl4 Cu2 N4 O8 S2'
_chemical_formula_sum            'C24 H20 Cl4 Cu2 N4 O8 S2'
_chemical_formula_weight         825.44
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-01 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                101.778(4)
_cell_angle_beta                 100.435(4)
_cell_angle_gamma                109.621(6)
_cell_formula_units_Z            1
_cell_length_a                   7.7848(5)
_cell_length_b                   9.0261(6)
_cell_length_c                   11.9040(5)
_cell_measurement_reflns_used    3098
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.6270
_cell_measurement_theta_min      3.8910
_cell_volume                     742.48(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7240
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.246
_diffrn_reflns_theta_min         3.941
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_description       platelet
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0400
_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)+(0.0723P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2666
_reflns_number_total             3047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt04061d2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7706448--7706452.cif.'
_cod_original_cell_volume        742.48(8)
_cod_database_code               7706449
_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_min   0.425
_shelx_estimated_absorpt_t_max   0.875
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
Cu1 Cu 0.78856(5) 0.49553(4) 0.52200(3) 0.01654(14) Uani 1 1 d . . . . .
Cl1 Cl 0.84634(8) 0.30699(7) 0.39366(5) 0.01860(16) Uani 1 1 d . . . . .
Cl2 Cl 0.74391(10) 0.34636(8) 0.65009(5) 0.02501(17) Uani 1 1 d . . . . .
N1 N 0.7655(3) 0.6273(3) 0.40142(18) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.7416(4) 0.7678(3) 0.4448(2) 0.0186(5) Uani 1 1 d . . . . .
C3 C 0.7341(4) 0.8765(3) 0.3787(2) 0.0202(5) Uani 1 1 d . . . . .
H3 H 0.724147 0.976984 0.412970 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7415(4) 0.8349(3) 0.2607(2) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.7585(4) 0.6871(3) 0.2140(2) 0.0194(5) Uani 1 1 d . . . . .
C6 C 0.7751(4) 0.5890(3) 0.2890(2) 0.0196(5) Uani 1 1 d . . . . .
H6 H 0.793875 0.491491 0.258786 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7157(4) 0.7846(3) 0.5640(2) 0.0189(5) Uani 1 1 d . . . . .
S8 S 0.66708(10) 0.93549(8) 0.64858(6) 0.02445(17) Uani 1 1 d . . . . .
C9 C 0.6484(4) 0.8341(4) 0.7550(2) 0.0250(5) Uani 1 1 d . . . . .
H9 H 0.620573 0.871155 0.827500 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6784(4) 0.6939(3) 0.7225(2) 0.0220(5) Uani 1 1 d . . . . .
H10 H 0.673438 0.621160 0.770472 0.026 Uiso 1 1 calc R U . . .
N11 N 0.7164(3) 0.6672(3) 0.61397(19) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.7149(4) 0.9448(3) 0.1852(2) 0.0205(5) Uani 1 1 d . . . . .
O13 O 0.5648(3) 0.9550(2) 0.15285(17) 0.0252(4) Uani 1 1 d . . . . .
O14 O 0.8758(3) 1.0282(3) 0.16433(17) 0.0250(4) Uani 1 1 d . . . . .
C15 C 0.8637(5) 1.1359(4) 0.0912(3) 0.0310(6) Uani 1 1 d . . . . .
H15A H 0.744604 1.082813 0.027710 0.047 Uiso 1 1 calc R U . . .
H15B H 0.970616 1.159093 0.055731 0.047 Uiso 1 1 calc R U . . .
H15C H 0.867782 1.238890 0.140501 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7461(4) 0.6280(3) 0.0851(2) 0.0208(5) Uani 1 1 d . . . . .
O17 O 0.6995(4) 0.6910(3) 0.01135(17) 0.0320(5) Uani 1 1 d . . . . .
O18 O 0.7837(3) 0.4937(2) 0.06050(16) 0.0239(4) Uani 1 1 d . . . . .
C19 C 0.7652(4) 0.4248(3) -0.0644(2) 0.0253(5) Uani 1 1 d . . . . .
H19A H 0.637620 0.402373 -0.111672 0.038 Uiso 1 1 calc R U . . .
H19B H 0.786529 0.322455 -0.075056 0.038 Uiso 1 1 calc R U . . .
H19C H 0.859065 0.503211 -0.090851 0.038 Uiso 1 1 calc 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 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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'
S S 0.3331 0.5567 '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
N11 Cu1 N1 79.32(9) . . ?
N11 Cu1 Cl2 93.22(7) . . ?
N1 Cu1 Cl2 166.63(7) . . ?
N11 Cu1 Cl1 171.49(7) . . ?
N1 Cu1 Cl1 93.12(6) . . ?
Cl2 Cu1 Cl1 93.41(3) . . ?
N11 Cu1 Cl1 90.59(7) . 2_766 ?
N1 Cu1 Cl1 88.00(6) . 2_766 ?
Cl2 Cu1 Cl1 103.28(3) . 2_766 ?
Cl1 Cu1 Cl1 93.08(2) . 2_766 ?
Cu1 Cl1 Cu1 86.92(2) . 2_766 ?
C6 N1 C2 118.6(2) . . ?
C6 N1 Cu1 126.74(18) . . ?
C2 N1 Cu1 114.67(17) . . ?
N1 C2 C3 122.7(2) . . ?
N1 C2 C7 112.1(2) . . ?
C3 C2 C7 125.2(2) . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 C12 118.6(2) . . ?
C5 C4 C12 122.1(2) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 C16 121.3(2) . . ?
C6 C5 C16 120.0(2) . . ?
N1 C6 C5 122.5(2) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N11 C7 C2 118.7(2) . . ?
N11 C7 S8 113.3(2) . . ?
C2 C7 S8 127.9(2) . . ?
C9 S8 C7 89.67(13) . . ?
C10 C9 S8 111.2(2) . . ?
C10 C9 H9 124.4 . . ?
S8 C9 H9 124.4 . . ?
C9 C10 N11 113.5(2) . . ?
C9 C10 H10 123.2 . . ?
N11 C10 H10 123.2 . . ?
C7 N11 C10 112.3(2) . . ?
C7 N11 Cu1 114.31(18) . . ?
C10 N11 Cu1 133.23(19) . . ?
O13 C12 O14 126.4(2) . . ?
O13 C12 C4 122.2(3) . . ?
O14 C12 C4 111.4(2) . . ?
C12 O14 C15 115.4(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O17 C16 O18 124.1(2) . . ?
O17 C16 C5 123.7(3) . . ?
O18 C16 C5 112.1(2) . . ?
C16 O18 C19 115.0(2) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 N11 2.007(2) . ?
Cu1 N1 2.062(2) . ?
Cu1 Cl2 2.2304(7) . ?
Cu1 Cl1 2.2658(6) . ?
Cu1 Cl1 2.6640(7) 2_766 ?
N1 C6 1.334(3) . ?
N1 C2 1.355(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.454(3) . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(4) . ?
C4 C12 1.507(3) . ?
C5 C6 1.399(3) . ?
C5 C16 1.492(3) . ?
C6 H6 0.9500 . ?
C7 N11 1.318(3) . ?
C7 S8 1.713(3) . ?
S8 C9 1.707(3) . ?
C9 C10 1.355(4) . ?
C9 H9 0.9500 . ?
C10 N11 1.369(3) . ?
C10 H10 0.9500 . ?
C12 O13 1.202(4) . ?
C12 O14 1.324(4) . ?
O14 C15 1.446(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O17 1.205(3) . ?
C16 O18 1.329(3) . ?
O18 C19 1.450(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
_geom_hbond_publ_flag
C6 H6 Cl1 0.95 2.61 3.215(3) 121.6 . yes
C9 H9 O13 0.95 2.47 3.084(3) 122.4 2_676 yes
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
C6 N1 C2 C3 -2.6(4) . . . . ?
Cu1 N1 C2 C3 176.3(2) . . . . ?
C6 N1 C2 C7 174.5(2) . . . . ?
Cu1 N1 C2 C7 -6.6(3) . . . . ?
N1 C2 C3 C4 3.5(4) . . . . ?
C7 C2 C3 C4 -173.2(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 C12 174.3(2) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C12 C4 C5 C6 -177.4(2) . . . . ?
C3 C4 C5 C16 173.3(2) . . . . ?
C12 C4 C5 C16 -1.6(4) . . . . ?
C2 N1 C6 C5 -1.0(4) . . . . ?
Cu1 N1 C6 C5 -179.74(19) . . . . ?
C4 C5 C6 N1 3.5(4) . . . . ?
C16 C5 C6 N1 -172.4(2) . . . . ?
N1 C2 C7 N11 -0.6(4) . . . . ?
C3 C2 C7 N11 176.4(3) . . . . ?
N1 C2 C7 S8 -175.76(19) . . . . ?
C3 C2 C7 S8 1.2(4) . . . . ?
N11 C7 S8 C9 0.2(2) . . . . ?
C2 C7 S8 C9 175.6(3) . . . . ?
C7 S8 C9 C10 -0.2(2) . . . . ?
S8 C9 C10 N11 0.1(3) . . . . ?
C2 C7 N11 C10 -176.0(2) . . . . ?
S8 C7 N11 C10 -0.2(3) . . . . ?
C2 C7 N11 Cu1 7.7(3) . . . . ?
S8 C7 N11 Cu1 -176.45(11) . . . . ?
C9 C10 N11 C7 0.0(4) . . . . ?
C9 C10 N11 Cu1 175.4(2) . . . . ?
C3 C4 C12 O13 -69.6(3) . . . . ?
C5 C4 C12 O13 105.3(3) . . . . ?
C3 C4 C12 O14 108.4(3) . . . . ?
C5 C4 C12 O14 -76.7(3) . . . . ?
O13 C12 O14 C15 -2.7(4) . . . . ?
C4 C12 O14 C15 179.3(2) . . . . ?
C4 C5 C16 O17 -9.0(4) . . . . ?
C6 C5 C16 O17 166.8(3) . . . . ?
C4 C5 C16 O18 173.9(2) . . . . ?
C6 C5 C16 O18 -10.2(4) . . . . ?
O17 C16 O18 C19 0.1(4) . . . . ?
C5 C16 O18 C19 177.1(2) . . . . ?
