#------------------------------------------------------------------------------
#$Date: 2023-02-02 04:31:46 +0200 (Thu, 02 Feb 2023) $
#$Revision: 280744 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246231.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_7246231
loop_
_publ_author_name
'Andrejević, Tina P.'
'Aleksic, Ivana'
'Kljun, Jakob'
'Počkaj, Marta'
'Zlatar, Matija'
'Vojnovic, Sandra'
'Nikodinovic-Runic, Jasmina'
'Turel, Iztok'
'Djuran, Miloš I.'
'Glišić, Biljana Đ.'
_publ_section_title
;
 Copper(ii) and silver(i) complexes with dimethyl
 6-(pyrazine-2-yl)pyridine-3,4-dicarboxylate (py-2pz): the influence of
 the metal ion on the antimicrobial potential of the complex
;
_journal_issue                   7
_journal_name_full               'RSC Advances'
_journal_page_first              4376
_journal_page_last               4393
_journal_paper_doi               10.1039/D2RA07401J
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C26 H22 Cl4 Cu2 N6 O8'
_chemical_formula_sum            'C26 H22 Cl4 Cu2 N6 O8'
_chemical_formula_weight         815.37
_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
_audit_creation_date             2022-10-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-16 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                104.394(6)
_cell_angle_beta                 106.396(6)
_cell_angle_gamma                104.368(6)
_cell_formula_units_Z            1
_cell_length_a                   7.7916(6)
_cell_length_b                   8.9848(6)
_cell_length_c                   11.9955(7)
_cell_measurement_reflns_used    2534
_cell_measurement_temperature    149.5(8)
_cell_measurement_theta_max      29.9110
_cell_measurement_theta_min      2.8940
_cell_volume                     733.10(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.5(8)
_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 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  90.00   1.00    2.32    --   14.21  37.00  60.00   87
  2  ω    -59.00  39.00   1.00    2.32    --   14.21 -57.00 -90.00   98
  3  ω    -10.00  88.00   1.00    2.32    --   14.21  57.00 150.00   98
  4  ω    -40.00  16.00   1.00    2.32    --  -14.52 -77.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0372532000
_diffrn_orient_matrix_UB_12      -0.0613521000
_diffrn_orient_matrix_UB_13      -0.0209742000
_diffrn_orient_matrix_UB_21      0.0876919000
_diffrn_orient_matrix_UB_22      0.0439285000
_diffrn_orient_matrix_UB_23      0.0504862000
_diffrn_orient_matrix_UB_31      -0.0335274000
_diffrn_orient_matrix_UB_32      -0.0428019000
_diffrn_orient_matrix_UB_33      0.0362832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6360
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.491
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_description       block
_exptl_crystal_F_000             410
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0339
_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)+(0.0248P)²+0.1293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2769
_reflns_number_total             3355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra07401j2.cif
_cod_data_source_block           moc40
_cod_original_cell_volume        733.10(9)
_cod_database_code               7246231
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Cu1 Cl2 C13 N11 N3 O4'
_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   0.912
_shelx_estimated_absorpt_t_min   0.705
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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:
 C5A(H5A), C12A(H12A), C9A(H9A), C2A(H2A), C11A(H11A)
2.b Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C20A(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.738
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 0.21380(4) 0.48611(4) 0.49641(3) 0.01471(10) Uani 1 1 d . . . . .
Cl2 Cl 0.15548(9) 0.68994(8) 0.61780(5) 0.01671(15) Uani 1 1 d . . . . .
Cl1 Cl 0.26351(10) 0.62601(8) 0.37241(6) 0.02183(16) Uani 1 1 d . . . . .
O19A O 0.1043(3) -0.0330(2) 0.83837(16) 0.0215(4) Uani 1 1 d . . . . .
O18A O 0.4227(3) 0.0525(3) 0.89085(17) 0.0286(5) Uani 1 1 d . . . . .
O15A O 0.2395(3) 0.5361(2) 0.96600(16) 0.0246(5) Uani 1 1 d . . . . .
N7A N 0.2802(3) 0.2975(3) 0.40727(18) 0.0145(5) Uani 1 1 d . . . . .
N1A N 0.2323(3) 0.3636(3) 0.61891(18) 0.0143(4) Uani 1 1 d . . . . .
O14A O 0.2588(3) 0.3107(3) 1.00803(17) 0.0346(5) Uani 1 1 d . . . . .
N10A N 0.3335(3) 0.0108(3) 0.2940(2) 0.0243(5) Uani 1 1 d . . . . .
C5A C 0.2478(4) 0.1115(3) 0.6450(2) 0.0173(6) Uani 1 1 d . . . . .
H5A H 0.252604 0.007822 0.612647 0.021 Uiso 1 1 calc R U . . .
C6A C 0.2454(3) 0.2140(3) 0.5761(2) 0.0147(5) Uani 1 1 d . . . . .
C8A C 0.2698(3) 0.1771(3) 0.4557(2) 0.0156(5) Uani 1 1 d . . . . .
C12A C 0.3222(3) 0.2774(3) 0.3060(2) 0.0177(6) Uani 1 1 d . . . . .
H12A H 0.331376 0.359042 0.270846 0.021 Uiso 1 1 calc R U . . .
C4A C 0.2431(3) 0.1641(3) 0.7622(2) 0.0163(6) Uani 1 1 d . . . . .
C9A C 0.2910(4) 0.0327(3) 0.3958(2) 0.0208(6) Uani 1 1 d . . . . .
H9A H 0.274959 -0.051772 0.427877 0.025 Uiso 1 1 calc R U . . .
C17A C 0.2696(4) 0.0573(3) 0.8404(2) 0.0187(6) Uani 1 1 d . . . . .
C2A C 0.2257(4) 0.4137(3) 0.7315(2) 0.0169(6) Uani 1 1 d . . . . .
H2A H 0.214815 0.515765 0.760220 0.020 Uiso 1 1 calc R U . . .
C11A C 0.3525(4) 0.1359(3) 0.2523(2) 0.0218(6) Uani 1 1 d . . . . .
H11A H 0.387924 0.127730 0.183790 0.026 Uiso 1 1 calc R U . . .
C3A C 0.2345(3) 0.3193(3) 0.8077(2) 0.0152(5) Uani 1 1 d . . . . .
C13A C 0.2442(4) 0.3858(3) 0.9375(2) 0.0185(6) Uani 1 1 d . . . . .
C16A C 0.2499(4) 0.6086(4) 1.0917(2) 0.0264(7) Uani 1 1 d . . . . .
H16A H 0.137387 0.549916 1.101587 0.040 Uiso 1 1 calc R U . . .
H16B H 0.259092 0.720955 1.106988 0.040 Uiso 1 1 calc R U . . .
H16C H 0.360023 0.602876 1.149266 0.040 Uiso 1 1 calc R U . . .
C20A C 0.1176(4) -0.1421(4) 0.9095(3) 0.0263(7) Uani 1 1 d . . . . .
H20A H 0.087333 -0.250920 0.854738 0.039 Uiso 1 1 calc R U . . .
H20B H 0.029584 -0.142039 0.951584 0.039 Uiso 1 1 calc R U . . .
H20C H 0.244790 -0.105341 0.969002 0.039 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 0.0033 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'
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
Cl2 Cu1 Cl2 92.39(2) . 2_566 ?
Cl1 Cu1 Cl2 92.30(3) . . ?
Cl1 Cu1 Cl2 101.98(3) . 2_566 ?
N7A Cu1 Cl2 172.80(6) . . ?
N7A Cu1 Cl2 90.17(6) . 2_566 ?
N7A Cu1 Cl1 93.76(6) . . ?
N7A Cu1 N1A 79.90(8) . . ?
N1A Cu1 Cl2 93.38(6) . . ?
N1A Cu1 Cl2 89.63(6) . 2_566 ?
N1A Cu1 Cl1 166.85(6) . . ?
Cu1 Cl2 Cu1 87.61(2) . 2_566 ?
C17A O19A C20A 115.2(2) . . ?
C13A O15A C16A 115.2(2) . . ?
C8A N7A Cu1 114.28(15) . . ?
C12A N7A Cu1 127.75(18) . . ?
C12A N7A C8A 117.9(2) . . ?
C6A N1A Cu1 114.51(15) . . ?
C2A N1A Cu1 126.66(18) . . ?
C2A N1A C6A 118.8(2) . . ?
C11A N10A C9A 115.6(2) . . ?
C6A C5A H5A 120.2 . . ?
C6A C5A C4A 119.5(2) . . ?
C4A C5A H5A 120.2 . . ?
N1A C6A C5A 121.7(2) . . ?
N1A C6A C8A 114.3(2) . . ?
C5A C6A C8A 123.9(2) . . ?
N7A C8A C6A 115.5(2) . . ?
N7A C8A C9A 120.2(2) . . ?
C9A C8A C6A 124.2(2) . . ?
N7A C12A H12A 119.8 . . ?
N7A C12A C11A 120.4(3) . . ?
C11A C12A H12A 119.8 . . ?
C5A C4A C17A 117.9(2) . . ?
C5A C4A C3A 118.9(2) . . ?
C3A C4A C17A 122.8(2) . . ?
N10A C9A C8A 122.5(3) . . ?
N10A C9A H9A 118.8 . . ?
C8A C9A H9A 118.8 . . ?
O19A C17A C4A 111.9(2) . . ?
O18A C17A O19A 126.3(2) . . ?
O18A C17A C4A 121.7(2) . . ?
N1A C2A H2A 118.7 . . ?
N1A C2A C3A 122.6(2) . . ?
C3A C2A H2A 118.7 . . ?
N10A C11A C12A 123.2(2) . . ?
N10A C11A H11A 118.4 . . ?
C12A C11A H11A 118.4 . . ?
C4A C3A C2A 118.4(2) . . ?
C4A C3A C13A 120.6(2) . . ?
C2A C3A C13A 121.0(2) . . ?
O15A C13A C3A 112.4(2) . . ?
O14A C13A O15A 124.4(2) . . ?
O14A C13A C3A 123.2(3) . . ?
O15A C16A H16A 109.5 . . ?
O15A C16A H16B 109.5 . . ?
O15A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
O19A C20A H20A 109.5 . . ?
O19A C20A H20B 109.5 . . ?
O19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 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 Cl2 2.2674(7) . ?
Cu1 Cl2 2.6638(8) 2_566 ?
Cu1 Cl1 2.2260(7) . ?
Cu1 N7A 2.032(2) . ?
Cu1 N1A 2.038(2) . ?
O19A C17A 1.331(3) . ?
O19A C20A 1.455(3) . ?
O18A C17A 1.193(3) . ?
O15A C13A 1.321(3) . ?
O15A C16A 1.456(3) . ?
N7A C8A 1.345(3) . ?
N7A C12A 1.327(3) . ?
N1A C6A 1.355(3) . ?
N1A C2A 1.333(3) . ?
O14A C13A 1.204(3) . ?
N10A C9A 1.335(3) . ?
N10A C11A 1.331(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.382(3) . ?
C5A C4A 1.382(3) . ?
C6A C8A 1.477(3) . ?
C8A C9A 1.392(4) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.384(4) . ?
C4A C17A 1.509(4) . ?
C4A C3A 1.391(4) . ?
C9A H9A 0.9300 . ?
C2A H2A 0.9300 . ?
C2A C3A 1.393(3) . ?
C11A H11A 0.9300 . ?
C3A C13A 1.495(3) . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
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
Cu1 N7A C8A C6A -10.1(3) . . . . ?
Cu1 N7A C8A C9A 172.89(19) . . . . ?
Cu1 N7A C12A C11A -175.85(19) . . . . ?
Cu1 N1A C6A C5A -176.16(19) . . . . ?
Cu1 N1A C6A C8A 7.8(3) . . . . ?
Cu1 N1A C2A C3A 178.24(19) . . . . ?
N7A C8A C9A N10A 4.2(4) . . . . ?
N7A C12A C11A N10A 3.1(4) . . . . ?
N1A C6A C8A N7A 1.5(3) . . . . ?
N1A C6A C8A C9A 178.4(2) . . . . ?
N1A C2A C3A C4A -2.6(4) . . . . ?
N1A C2A C3A C13A 174.5(2) . . . . ?
C5A C6A C8A N7A -174.4(2) . . . . ?
C5A C6A C8A C9A 2.5(4) . . . . ?
C5A C4A C17A O19A -99.5(3) . . . . ?
C5A C4A C17A O18A 76.8(3) . . . . ?
C5A C4A C3A C2A 1.8(4) . . . . ?
C5A C4A C3A C13A -175.3(2) . . . . ?
C6A N1A C2A C3A 1.0(4) . . . . ?
C6A C5A C4A C17A -172.8(2) . . . . ?
C6A C5A C4A C3A 0.5(4) . . . . ?
C6A C8A C9A N10A -172.5(2) . . . . ?
C8A N7A C12A C11A 0.5(4) . . . . ?
C12A N7A C8A C6A 173.0(2) . . . . ?
C12A N7A C8A C9A -4.0(4) . . . . ?
C4A C5A C6A N1A -2.2(4) . . . . ?
C4A C5A C6A C8A 173.5(2) . . . . ?
C4A C3A C13A O15A 178.2(2) . . . . ?
C4A C3A C13A O14A -0.3(4) . . . . ?
C9A N10A C11A C12A -2.9(4) . . . . ?
C17A C4A C3A C2A 174.7(2) . . . . ?
C17A C4A C3A C13A -2.3(4) . . . . ?
C2A N1A C6A C5A 1.4(4) . . . . ?
C2A N1A C6A C8A -174.6(2) . . . . ?
C2A C3A C13A O15A 1.2(3) . . . . ?
C2A C3A C13A O14A -177.3(3) . . . . ?
C11A N10A C9A C8A -0.7(4) . . . . ?
C3A C4A C17A O19A 87.5(3) . . . . ?
C3A C4A C17A O18A -96.2(3) . . . . ?
C16A O15A C13A O14A -1.1(4) . . . . ?
C16A O15A C13A C3A -179.6(2) . . . . ?
C20A O19A C17A O18A 2.5(4) . . . . ?
C20A O19A C17A C4A 178.7(2) . . . . ?
