#------------------------------------------------------------------------------
#$Date: 2024-07-05 19:59:36 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/58/7715858.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_7715858
loop_
_publ_author_name
'García-García, Amalia'
'Medina-O'donnell, Marta'
'Rojas, Sara'
'Cano-Morenilla, Mariola'
'Morales, Juan'
'Quesada-Moreno, María Mar'
'Sainz, Juan'
'Vitorica-Yrezabal, Iñigo J'
'Rodríguez-Diéguez, Antonio'
'Navarro, Amparo'
'Reyes-Zurita, Fernando J'
_publ_section_title
;
 Modulating anti-inflammatory and anticancer properties by designing a
 family of metal-complexes based on 5-nitropicolinic acid.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8988
_journal_page_last               9000
_journal_paper_doi               10.1039/d4dt00265b
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C12 H6 Cu N4 O8'
_chemical_formula_sum            'C12 H6 Cu N4 O8'
_chemical_formula_weight         397.75
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.370(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4800(8)
_cell_length_b                   10.0354(12)
_cell_length_c                   10.6890(11)
_cell_measurement_reflns_used    3553
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.84
_cell_volume                     666.92(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0522
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9205
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_min         2.840
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.697
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.9151.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_description       block
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.193
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0280
_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)+(0.0563P)²+0.0508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1208
_reflns_number_total             1372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00265b2.cif
_cod_data_source_block           Compound3
_cod_depositor_comments
'Adding full bibliography for 7715854--7715859.cif.'
_cod_database_code               7715858
_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_max   0.835
_shelx_estimated_absorpt_t_min   0.750
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cu1 Cu 0.000000 0.500000 0.500000 0.02736(15) Uani 1 2 d S . P . .
O1 O -0.1945(2) 0.55504(15) 0.59828(12) 0.0327(3) Uani 1 1 d . . . . .
O2 O -0.2250(2) 0.55968(17) 0.80101(13) 0.0386(4) Uani 1 1 d . . . . .
O4 O 0.7348(3) 0.23500(15) 0.75055(16) 0.0433(4) Uani 1 1 d . . . . .
N1 N 0.1766(2) 0.43566(15) 0.66908(14) 0.0250(3) Uani 1 1 d . . . . .
N2 N 0.6694(3) 0.26196(16) 0.84393(17) 0.0338(4) Uani 1 1 d . . . . .
O3 O 0.7640(3) 0.23163(18) 0.95593(15) 0.0554(5) Uani 1 1 d . . . . .
C2 C 0.0855(3) 0.45985(19) 0.76534(18) 0.0247(4) Uani 1 1 d . . . . .
C1 C -0.1311(3) 0.53154(19) 0.72073(19) 0.0273(4) Uani 1 1 d . . . . .
C5 C 0.4663(3) 0.33372(17) 0.82026(17) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.3660(3) 0.37464(17) 0.69457(18) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.430401 0.359679 0.628287 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3792(3) 0.35905(19) 0.92116(18) 0.0313(4) Uani 1 1 d . . . . .
H4 H 0.449716 0.333613 1.006123 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1832(3) 0.42360(19) 0.89185(18) 0.0310(4) Uani 1 1 d . . . . .
H3 H 0.118187 0.442248 0.957138 0.037 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'
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
O1 Cu1 O1 180.0 . 3_566 ?
O1 Cu1 N1 83.88(6) 3_566 3_566 ?
O1 Cu1 N1 83.88(6) . . ?
O1 Cu1 N1 96.12(6) . 3_566 ?
O1 Cu1 N1 96.12(6) 3_566 . ?
N1 Cu1 N1 180.0 . 3_566 ?
C1 O1 Cu1 115.63(12) . . ?
C2 N1 Cu1 112.26(12) . . ?
C6 N1 Cu1 127.38(12) . . ?
C6 N1 C2 120.35(15) . . ?
O4 N2 C5 118.19(16) . . ?
O3 N2 O4 123.58(18) . . ?
O3 N2 C5 118.23(17) . . ?
N1 C2 C1 114.11(15) . . ?
N1 C2 C3 121.79(17) . . ?
C3 C2 C1 124.09(16) . . ?
O1 C1 C2 114.09(16) . . ?
O2 C1 O1 126.78(18) . . ?
O2 C1 C2 119.14(17) . . ?
C6 C5 N2 118.04(16) . . ?
C4 C5 N2 120.35(16) . . ?
C4 C5 C6 121.61(17) . . ?
N1 C6 C5 119.39(16) . . ?
N1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C5 C4 H4 121.2 . . ?
C5 C4 C3 117.62(16) . . ?
C3 C4 H4 121.2 . . ?
C2 C3 C4 119.19(17) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
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 O1 1.9348(13) . ?
Cu1 O1 1.9348(13) 3_566 ?
Cu1 N1 1.9562(14) . ?
Cu1 N1 1.9562(14) 3_566 ?
O1 C1 1.278(2) . ?
O2 C1 1.217(2) . ?
O4 N2 1.220(2) . ?
N1 C2 1.345(2) . ?
N1 C6 1.330(2) . ?
N2 O3 1.220(2) . ?
N2 C5 1.458(2) . ?
C2 C1 1.529(3) . ?
C2 C3 1.371(3) . ?
C5 C6 1.380(2) . ?
C5 C4 1.375(3) . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.381(3) . ?
C3 H3 0.9300 . ?
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 O1 C1 O2 178.56(17) . . . . ?
Cu1 O1 C1 C2 -1.8(2) . . . . ?
Cu1 N1 C2 C1 -0.27(19) . . . . ?
Cu1 N1 C2 C3 -179.59(15) . . . . ?
Cu1 N1 C6 C5 -178.79(13) . . . . ?
O4 N2 C5 C6 -4.0(3) . . . . ?
O4 N2 C5 C4 175.93(18) . . . . ?
N1 C2 C1 O1 1.4(2) . . . . ?
N1 C2 C1 O2 -178.95(18) . . . . ?
N1 C2 C3 C4 -0.8(3) . . . . ?
N2 C5 C6 N1 177.38(16) . . . . ?
N2 C5 C4 C3 -177.95(17) . . . . ?
O3 N2 C5 C6 176.30(18) . . . . ?
O3 N2 C5 C4 -3.7(3) . . . . ?
C2 N1 C6 C5 1.4(3) . . . . ?
C1 C2 C3 C4 179.97(18) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C6 N1 C2 C1 179.56(17) . . . . ?
C6 N1 C2 C3 0.2(3) . . . . ?
C6 C5 C4 C3 2.0(3) . . . . ?
C4 C5 C6 N1 -2.6(3) . . . . ?
C3 C2 C1 O1 -179.33(18) . . . . ?
C3 C2 C1 O2 0.3(3) . . . . ?
