#------------------------------------------------------------------------------
#$Date: 2021-08-26 11:38:11 +0300 (Thu, 26 Aug 2021) $
#$Revision: 268250 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/44/1564422.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_1564422
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 H12 Cl4 Cu N4 O4 S2'
_chemical_formula_sum            'C20 H12 Cl4 Cu N4 O4 S2'
_chemical_formula_weight         641.80
_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     dual
_cell_angle_alpha                103.2830(10)
_cell_angle_beta                 102.8400(10)
_cell_angle_gamma                104.336(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6656(3)
_cell_length_b                   11.7200(4)
_cell_length_c                   12.9228(3)
_cell_measurement_reflns_used    4167
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.54
_cell_volume                     1182.10(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.989
_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  0.0385
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14014
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.119
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.591
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0721 before and 0.0477 after correction. The Ratio of minimum to maximum transmission is 0.7737. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_description       plate
_exptl_crystal_F_000             642
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0357
_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)+(0.0188P)²+0.9617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4296
_reflns_number_total             5160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3.cif
_cod_data_source_block           lt12_1
_cod_original_cell_volume        1182.10(6)
_cod_database_code               1564422
_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   0.897
_shelx_estimated_absorpt_t_min   0.622
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C30(H30), C31(H31), C32(H32), C34(H34), C37(H37), C39(H39)
2.b Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C41(H41A,H41B,H41C)
;
_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 0.34235(4) 0.35966(3) 0.66726(2) 0.01668(9) Uani 1 1 d . . . . .
Cl11 Cl -0.13838(8) 0.36038(6) 0.79061(5) 0.02605(15) Uani 1 1 d . . . . .
Cl12 Cl -0.24145(9) 0.56314(7) 0.97578(6) 0.03035(17) Uani 1 1 d . . . . .
Cl21 Cl 0.03748(11) 0.02166(7) 0.87876(7) 0.0423(2) Uani 1 1 d . . . . .
Cl22 Cl 0.40455(12) 0.10572(7) 1.06428(6) 0.0437(2) Uani 1 1 d . . . . .
S11 S 0.05290(9) 0.74060(6) 0.95270(6) 0.02635(16) Uani 1 1 d . . . . .
S21 S 0.51054(9) 0.25049(7) 0.91459(6) 0.02785(16) Uani 1 1 d . . . . .
O11 O 0.2804(2) 0.46606(16) 0.77955(14) 0.0208(4) Uani 1 1 d . . . . .
O12 O 0.1466(3) 0.5263(2) 0.64368(16) 0.0372(5) Uani 1 1 d . . . . .
O21 O 0.1287(2) 0.23336(16) 0.62544(14) 0.0239(4) Uani 1 1 d . . . . .
O22 O -0.0459(3) 0.0862(2) 0.66351(18) 0.0427(6) Uani 1 1 d . . . . .
N11 N 0.1639(3) 0.6989(2) 0.87051(18) 0.0242(5) Uani 1 1 d . . . . .
N21 N 0.3780(3) 0.24835(19) 0.80037(18) 0.0216(5) Uani 1 1 d . . . . .
N31 N 0.4176(2) 0.25999(18) 0.55263(16) 0.0162(4) Uani 1 1 d . . . . .
N32 N 0.5386(2) 0.49051(18) 0.66881(16) 0.0156(4) Uani 1 1 d . . . . .
C11 C 0.1818(3) 0.5191(2) 0.7385(2) 0.0216(6) Uani 1 1 d . . . . .
C12 C 0.1024(3) 0.5793(2) 0.8197(2) 0.0189(5) Uani 1 1 d . . . . .
C13 C -0.0387(3) 0.5157(2) 0.8458(2) 0.0190(5) Uani 1 1 d . . . . .
C14 C -0.0806(3) 0.5953(2) 0.9205(2) 0.0212(6) Uani 1 1 d . . . . .
C21 C 0.0894(3) 0.1632(2) 0.6841(2) 0.0247(6) Uani 1 1 d . . . . .
C22 C 0.2267(3) 0.1766(2) 0.7856(2) 0.0207(6) Uani 1 1 d . . . . .
C23 C 0.2132(4) 0.1182(2) 0.8699(2) 0.0250(6) Uani 1 1 d . . . . .
C24 C 0.3630(4) 0.1513(2) 0.9480(2) 0.0293(7) Uani 1 1 d . . . . .
C30 C 0.5850(3) 0.6107(2) 0.7255(2) 0.0186(5) Uani 1 1 d . . . . .
H30 H 0.524582 0.637251 0.774079 0.022 Uiso 1 1 calc R . . . .
C31 C 0.3437(3) 0.1411(2) 0.4945(2) 0.0197(5) Uani 1 1 d . . . . .
H31 H 0.241652 0.098350 0.503784 0.024 Uiso 1 1 calc R . . . .
C32 C 0.4100(3) 0.0783(2) 0.4218(2) 0.0223(6) Uani 1 1 d . . . . .
H32 H 0.353180 -0.005979 0.380649 0.027 Uiso 1 1 calc R . . . .
C33 C 0.5603(3) 0.1386(2) 0.4086(2) 0.0215(6) Uani 1 1 d . . . . .
C34 C 0.6355(3) 0.2625(2) 0.4676(2) 0.0197(5) Uani 1 1 d . . . . .
H34 H 0.737723 0.306869 0.459629 0.024 Uiso 1 1 calc R . . . .
C35 C 0.5616(3) 0.3213(2) 0.53783(19) 0.0152(5) Uani 1 1 d . . . . .
C36 C 0.6258(3) 0.4545(2) 0.59989(19) 0.0151(5) Uani 1 1 d . . . . .
C37 C 0.7595(3) 0.5365(2) 0.58742(19) 0.0158(5) Uani 1 1 d . . . . .
H37 H 0.818494 0.507740 0.538689 0.019 Uiso 1 1 calc R . . . .
C38 C 0.8081(3) 0.6609(2) 0.64585(19) 0.0169(5) Uani 1 1 d . . . . .
C39 C 0.7173(3) 0.6974(2) 0.7159(2) 0.0182(5) Uani 1 1 d . . . . .
H39 H 0.746165 0.781856 0.757132 0.022 Uiso 1 1 calc R . . . .
C40 C 0.6389(4) 0.0710(3) 0.3322(3) 0.0355(7) Uani 1 1 d . . . . .
H40A H 0.663953 0.116560 0.279985 0.053 Uiso 1 1 calc GR . . . .
H40B H 0.561555 -0.011915 0.290618 0.053 Uiso 1 1 calc GR . . . .
H40C H 0.742297 0.064553 0.376347 0.053 Uiso 1 1 calc GR . . . .
C41 C 0.9545(3) 0.7505(2) 0.6345(2) 0.0211(6) Uani 1 1 d . . . . .
H41A H 1.057685 0.743822 0.678634 0.032 Uiso 1 1 calc GR . . . .
H41B H 0.950074 0.834631 0.661236 0.032 Uiso 1 1 calc GR . . . .
H41C H 0.951775 0.732003 0.556047 0.032 Uiso 1 1 calc GR . . . .
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 N21 84.08(7) . .
O11 Cu1 N31 176.33(8) . .
O11 Cu1 N32 95.29(8) . .
O21 Cu1 O11 91.22(7) . .
O21 Cu1 N21 76.13(7) . .
O21 Cu1 N31 92.28(8) . .
O21 Cu1 N32 164.58(8) . .
N31 Cu1 N21 97.82(8) . .
N32 Cu1 N21 118.41(8) . .
N32 Cu1 N31 81.05(8) . .
N11 S11 C14 94.47(12) . .
N21 S21 C24 93.66(13) . .
C11 O11 Cu1 113.05(15) . .
C21 O21 Cu1 123.50(18) . .
C12 N11 S11 109.81(17) . .
S21 N21 Cu1 142.23(12) . .
C22 N21 Cu1 104.56(17) . .
C22 N21 S21 111.54(17) . .
C31 N31 Cu1 126.46(16) . .
C31 N31 C35 118.7(2) . .
C35 N31 Cu1 114.75(16) . .
C30 N32 Cu1 126.25(16) . .
C30 N32 C36 117.9(2) . .
C36 N32 Cu1 115.67(16) . .
O11 C11 C12 113.9(2) . .
O12 C11 O11 127.5(2) . .
O12 C11 C12 118.6(2) . .
N11 C12 C11 119.7(2) . .
N11 C12 C13 115.7(2) . .
C13 C12 C11 124.6(2) . .
C12 C13 Cl11 123.87(19) . .
C14 C13 Cl11 125.7(2) . .
C14 C13 C12 110.5(2) . .
S11 C14 Cl12 122.57(15) . .
C13 C14 Cl12 127.9(2) . .
C13 C14 S11 109.57(19) . .
O21 C21 C22 115.7(2) . .
O22 C21 O21 125.7(3) . .
O22 C21 C22 118.5(2) . .
N21 C22 C21 118.6(2) . .
N21 C22 C23 114.2(2) . .
C23 C22 C21 127.2(2) . .
C22 C23 Cl21 127.0(2) . .
C24 C23 Cl21 122.2(2) . .
C24 C23 C22 110.8(2) . .
Cl22 C24 S21 123.2(2) . .
C23 C24 Cl22 126.9(2) . .
C23 C24 S21 109.8(2) . .
N32 C30 C39 122.5(2) . .
N31 C31 C32 122.3(2) . .
C31 C32 C33 119.7(2) . .
C32 C33 C40 120.9(2) . .
C34 C33 C32 117.9(2) . .
C34 C33 C40 121.2(2) . .
C35 C34 C33 119.8(2) . .
N31 C35 C34 121.5(2) . .
N31 C35 C36 114.1(2) . .
C34 C35 C36 124.4(2) . .
N32 C36 C35 114.0(2) . .
N32 C36 C37 122.2(2) . .
C37 C36 C35 123.7(2) . .
C36 C37 C38 120.1(2) . .
C37 C38 C39 117.4(2) . .
C37 C38 C41 120.7(2) . .
C39 C38 C41 122.0(2) . .
C30 C39 C38 119.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O11 1.9480(17) .
Cu1 O21 1.9343(17) .
Cu1 N21 2.398(2) .
Cu1 N31 1.9988(19) .
Cu1 N32 1.9808(19) .
Cl11 C13 1.709(3) .
Cl12 C14 1.703(2) .
Cl21 C23 1.701(3) .
Cl22 C24 1.702(3) .
S11 N11 1.656(2) .
S11 C14 1.702(3) .
S21 N21 1.647(2) .
S21 C24 1.706(3) .
O11 C11 1.269(3) .
O12 C11 1.223(3) .
O21 C21 1.276(3) .
O22 C21 1.219(3) .
N11 C12 1.316(3) .
N21 C22 1.316(3) .
N31 C31 1.334(3) .
N31 C35 1.355(3) .
N32 C30 1.341(3) .
N32 C36 1.352(3) .
C11 C12 1.514(3) .
C12 C13 1.418(3) .
C13 C14 1.358(3) .
C21 C22 1.510(4) .
C22 C23 1.424(4) .
C23 C24 1.358(4) .
C30 C39 1.381(3) .
C31 C32 1.374(3) .
C32 C33 1.386(3) .
C33 C34 1.385(3) .
C33 C40 1.507(3) .
C34 C35 1.378(3) .
C35 C36 1.478(3) .
C36 C37 1.376(3) .
C37 C38 1.387(3) .
C38 C39 1.388(3) .
C38 C41 1.492(3) .
