#------------------------------------------------------------------------------
#$Date: 2021-08-26 11:42:50 +0300 (Thu, 26 Aug 2021) $
#$Revision: 268251 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/44/1564423.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_1564423
loop_
_publ_author_name
'Eremina, Julia A.'
'Lider, Elizaveta V.'
'Sukhikh, Taisiya S.'
'Klyushova, Lyubov S.'
'Perepechaeva, Maria L.'
'Sheven', Dmitriy G.'
'Berezin, Alexey S.'
'Grishanova, Alevtina Y.'
'Potkin, Vladimir I.'
_publ_section_title
;
 Water-soluble copper(II) complexes with
 4,5-dichloro-isothiazole-3-carboxylic acid and heterocyclic N-donor
 ligands: Synthesis, crystal structures, cytotoxicity, and DNA binding
 study
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119778
_journal_paper_doi               10.1016/j.ica.2020.119778
_journal_volume                  510
_journal_year                    2020
_chemical_formula_moiety         'C20 H10 Cl4 Cu N4 O5 S2'
_chemical_formula_sum            'C20 H10 Cl4 Cu N4 O5 S2'
_chemical_formula_weight         655.78
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                74.098(2)
_cell_angle_beta                 87.919(2)
_cell_angle_gamma                76.745(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0973(4)
_cell_length_b                   9.3869(5)
_cell_length_c                   16.2056(7)
_cell_measurement_reflns_used    6217
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.76
_cell_measurement_theta_min      2.32
_cell_volume                     1152.60(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_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  0.0215
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9603
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.801
_diffrn_reflns_theta_min         2.317
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.637
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0504 before and 0.0324 after correction. The Ratio of minimum to maximum transmission is 0.8464. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.890
_exptl_crystal_description       prism
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0239
_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)+(0.0255P)²+0.8728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0613
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4019
_reflns_number_total             4396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            4.cif
_cod_data_source_block           elt20
_cod_original_cell_volume        1152.61(10)
_cod_database_code               1564423
_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   0.735
_shelx_estimated_absorpt_t_min   0.598
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C31(H31), C40(H40), C30(H30), C33(H33), C32(H32), C38(H38), C39(H39)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.60876(3) 0.77702(3) 0.64087(2) 0.01251(7) Uani 1 1 d . . . . .
Cl11 Cl -0.00145(6) 0.93294(6) 0.79047(3) 0.02370(12) Uani 1 1 d . . . . .
Cl21 Cl 0.63665(8) 0.74430(6) 0.94920(3) 0.02849(13) Uani 1 1 d . . . . .
S21 S 0.70147(7) 1.18957(6) 0.88812(3) 0.02434(13) Uani 1 1 d . . . . .
Cl22 Cl 0.79565(7) 0.94885(7) 1.05405(3) 0.02997(14) Uani 1 1 d . . . . .
Cl12 Cl 0.14038(8) 0.64896(7) 0.96646(3) 0.03343(14) Uani 1 1 d . . . . .
S11 S 0.38965(7) 0.54011(6) 0.84311(3) 0.02245(12) Uani 1 1 d . . . . .
O11 O 0.37919(16) 0.87847(16) 0.59258(8) 0.0164(3) Uani 1 1 d . . . . .
O21 O 0.60563(17) 0.85299(15) 0.74160(8) 0.0165(3) Uani 1 1 d . . . . .
O41 O 0.75165(18) 0.94953(17) 0.57634(9) 0.0210(3) Uani 1 1 d . . . . .
H41A H 0.751353 0.959274 0.522365 0.032 Uiso 1 1 d GR . . . .
H41B H 0.856338 0.917020 0.591877 0.032 Uiso 1 1 d GR . . . .
O12 O 0.09951(17) 0.92011(17) 0.60323(9) 0.0205(3) Uani 1 1 d . . . . .
O22 O 0.37258(18) 1.04529(17) 0.72510(10) 0.0238(3) Uani 1 1 d . . . . .
N32 N 0.80198(19) 0.59861(18) 0.69630(10) 0.0131(3) Uani 1 1 d . . . . .
N31 N 0.64352(19) 0.67319(18) 0.54540(10) 0.0136(3) Uani 1 1 d . . . . .
N11 N 0.3887(2) 0.63357(19) 0.74071(11) 0.0182(4) Uani 1 1 d . . . . .
N21 N 0.6087(2) 1.1631(2) 0.80601(11) 0.0203(4) Uani 1 1 d . . . . .
C36 C 0.8472(2) 0.4990(2) 0.64776(12) 0.0129(4) Uani 1 1 d . . . . .
C11 C 0.2442(2) 0.8615(2) 0.63329(12) 0.0148(4) Uani 1 1 d . . . . .
C37 C 0.9738(2) 0.3648(2) 0.67291(12) 0.0148(4) Uani 1 1 d . . . . .
C41 C 1.0109(3) 0.2668(2) 0.61721(13) 0.0179(4) Uani 1 1 d . . . . .
H41 H 1.095707 0.175016 0.634106 0.021 Uiso 1 1 calc R . . . .
C21 C 0.5110(2) 0.9712(2) 0.75697(12) 0.0142(4) Uani 1 1 d . . . . .
C35 C 0.7605(2) 0.5393(2) 0.56634(12) 0.0130(4) Uani 1 1 d . . . . .
C22 C 0.5883(2) 1.0221(2) 0.82483(12) 0.0148(4) Uani 1 1 d . . . . .
C12 C 0.2659(2) 0.7583(2) 0.72351(12) 0.0135(4) Uani 1 1 d . . . . .
C34 C 0.7994(2) 0.4422(2) 0.51282(12) 0.0145(4) Uani 1 1 d . . . . .
C31 C 0.5653(2) 0.7177(2) 0.46885(12) 0.0167(4) Uani 1 1 d . . . . .
H31 H 0.485115 0.812566 0.453084 0.020 Uiso 1 1 calc R . . . .
C40 C 0.9265(3) 0.3034(2) 0.54086(13) 0.0188(4) Uani 1 1 d . . . . .
H40 H 0.951973 0.236170 0.505374 0.023 Uiso 1 1 calc R . . . .
C30 C 0.8801(2) 0.5652(2) 0.77232(12) 0.0160(4) Uani 1 1 d . . . . .
H30 H 0.847757 0.632556 0.807424 0.019 Uiso 1 1 calc R . . . .
C33 C 0.7117(3) 0.4920(2) 0.43270(12) 0.0179(4) Uani 1 1 d . . . . .
H33 H 0.732096 0.430132 0.394122 0.021 Uiso 1 1 calc R . . . .
C32 C 0.5976(3) 0.6289(2) 0.41060(12) 0.0185(4) Uani 1 1 d . . . . .
H32 H 0.540390 0.663820 0.356138 0.022 Uiso 1 1 calc R . . . .
C14 C 0.2221(3) 0.6689(2) 0.86642(13) 0.0193(4) Uani 1 1 d . . . . .
C38 C 1.0574(3) 0.3342(2) 0.75269(13) 0.0177(4) Uani 1 1 d . . . . .
H38 H 1.146374 0.246110 0.772018 0.021 Uiso 1 1 calc R . . . .
C24 C 0.7121(3) 1.0100(2) 0.95214(12) 0.0191(4) Uani 1 1 d . . . . .
C39 C 1.0086(2) 0.4336(2) 0.80212(12) 0.0177(4) Uani 1 1 d . . . . .
H39 H 1.062164 0.413045 0.856670 0.021 Uiso 1 1 calc R . . . .
C23 C 0.6466(2) 0.9307(2) 0.90820(12) 0.0163(4) Uani 1 1 d . . . . .
C13 C 0.1655(2) 0.7822(2) 0.79429(12) 0.0155(4) 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 0.0033 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'
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'
S S 0.1246 0.1234 '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
O11 Cu1 O41 100.74(6) . .
O11 Cu1 N32 156.43(6) . .
O11 Cu1 N31 88.01(6) . .
O21 Cu1 O11 100.49(5) . .
O21 Cu1 O41 87.51(6) . .
O21 Cu1 N32 89.77(6) . .
O21 Cu1 N31 171.12(6) . .
N32 Cu1 O41 100.86(6) . .
N31 Cu1 O41 93.48(6) . .
N31 Cu1 N32 81.38(6) . .
N21 S21 C24 94.67(9) . .
N11 S11 C14 94.23(9) . .
C11 O11 Cu1 123.60(12) . .
C21 O21 Cu1 129.57(12) . .
C36 N32 Cu1 112.39(12) . .
C30 N32 Cu1 129.32(13) . .
C30 N32 C36 118.21(17) . .
C35 N31 Cu1 112.89(12) . .
C31 N31 Cu1 128.67(13) . .
C31 N31 C35 118.42(16) . .
C12 N11 S11 110.31(14) . .
C22 N21 S21 109.96(14) . .
N32 C36 C37 123.45(17) . .
N32 C36 C35 116.48(17) . .
C37 C36 C35 120.05(17) . .
O11 C11 C12 116.94(16) . .
O12 C11 O11 124.54(18) . .
O12 C11 C12 118.49(17) . .
C36 C37 C41 119.05(17) . .
C36 C37 C38 117.13(17) . .
C38 C37 C41 123.82(18) . .
C40 C41 C37 120.91(18) . .
O21 C21 C22 112.51(16) . .
O22 C21 O21 129.37(18) . .
O22 C21 C22 118.11(17) . .
N31 C35 C36 116.59(16) . .
N31 C35 C34 123.54(17) . .
C34 C35 C36 119.87(17) . .
N21 C22 C21 118.82(17) . .
N21 C22 C23 115.11(17) . .
C23 C22 C21 126.06(18) . .
N11 C12 C11 118.85(16) . .
N11 C12 C13 115.24(18) . .
C13 C12 C11 125.91(17) . .
C35 C34 C40 119.08(17) . .
C35 C34 C33 116.38(18) . .
C33 C34 C40 124.51(17) . .
N31 C31 C32 122.03(18) . .
C41 C40 C34 121.00(18) . .
N32 C30 C39 121.94(17) . .
C32 C33 C34 120.04(17) . .
C33 C32 C31 119.54(18) . .
S11 C14 Cl12 123.07(13) . .
C13 C14 Cl12 127.13(17) . .
C13 C14 S11 109.78(15) . .
C39 C38 C37 119.08(18) . .
Cl22 C24 S21 122.78(13) . .
C23 C24 S21 109.07(15) . .
C23 C24 Cl22 128.14(17) . .
C38 C39 C30 120.15(18) . .
C22 C23 Cl21 124.99(15) . .
C24 C23 Cl21 123.82(16) . .
C24 C23 C22 111.18(18) . .
C12 C13 Cl11 125.24(15) . .
C14 C13 Cl11 124.32(16) . .
C14 C13 C12 110.43(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O11 1.9647(13) .
Cu1 O21 1.9495(13) .
Cu1 O41 2.2130(14) .
Cu1 N32 2.0336(16) .
Cu1 N31 2.0229(15) .
Cl11 C13 1.707(2) .
Cl21 C23 1.712(2) .
S21 N21 1.6541(17) .
S21 C24 1.705(2) .
Cl22 C24 1.702(2) .
Cl12 C14 1.707(2) .
S11 N11 1.6502(17) .
S11 C14 1.704(2) .
O11 C11 1.275(2) .
O21 C21 1.276(2) .
O12 C11 1.230(2) .
O22 C21 1.222(2) .
N32 C36 1.361(2) .
N32 C30 1.330(2) .
N31 C35 1.355(2) .
N31 C31 1.329(2) .
N11 C12 1.320(2) .
N21 C22 1.322(3) .
C36 C37 1.400(3) .
C36 C35 1.431(3) .
C11 C12 1.507(3) .
C37 C41 1.435(3) .
C37 C38 1.408(3) .
C41 C40 1.355(3) .
C21 C22 1.518(3) .
C35 C34 1.402(3) .
C22 C23 1.418(3) .
C12 C13 1.420(3) .
C34 C40 1.434(3) .
C34 C33 1.411(3) .
C31 C32 1.403(3) .
C30 C39 1.401(3) .
C33 C32 1.364(3) .
C14 C13 1.357(3) .
C38 C39 1.373(3) .
C24 C23 1.358(3) .
