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#$Date: 2024-07-05 19:59:36 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293146 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/58/7715854.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_7715854
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_absolute_configuration ad
_chemical_formula_moiety         'C12 H6 Mn N4 O8'
_chemical_formula_sum            'C12 H6 Mn N4 O8'
_chemical_formula_weight         389.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-22
_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                 108.111(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4325(17)
_cell_length_b                   5.3198(7)
_cell_length_c                   12.7174(15)
_cell_measurement_reflns_used    537
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.51
_cell_measurement_theta_min      3.36
_cell_volume                     670.83(16)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.0740
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5298
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_min         2.054
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0964 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.8624.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_description       needle
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0543
_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)+(0.0235P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2051
_reflns_number_total             2717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00265b2.cif
_cod_data_source_block           Compound1
_cod_depositor_comments
'Adding full bibliography for 7715854--7715859.cif.'
_cod_database_code               7715854
_shelx_shelxl_version_number     2019/1
_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   0.979
_shelx_estimated_absorpt_t_min   0.725
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C6B(H6B), C6A(H6A), C5B(H5B), C8B(H8B), C3A(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
Mn1 Mn 0.22818(10) 0.7221(3) 0.51017(7) 0.0272(3) Uani 1 1 d . . . . .
O1 O 0.3060(6) 1.0502(10) 0.4481(4) 0.0316(13) Uani 1 1 d . . . . .
O2 O 0.3753(5) 1.4430(10) 0.4987(4) 0.0326(13) Uani 1 1 d . . . . .
O2A O -0.0465(5) 0.4465(10) 0.5227(4) 0.0357(14) Uani 1 1 d . . . . .
O1A O 0.1704(6) 0.4809(11) 0.6233(4) 0.0388(15) Uani 1 1 d . . . . .
N1A N -0.0893(6) 0.0969(12) 0.6583(5) 0.0301(16) Uani 1 1 d . . . . .
N1B N 0.3814(7) 0.9067(12) 0.6602(5) 0.0279(15) Uani 1 1 d . . . . .
O1B O 0.5748(8) 0.6080(17) 0.9613(6) 0.058(2) Uani 1 1 d . . . . .
N2B N 0.6057(9) 0.8210(18) 0.9473(6) 0.042(2) Uani 1 1 d . . . . .
O4A O -0.1661(7) -0.4115(15) 0.8656(5) 0.071(2) Uani 1 1 d . . . . .
N2A N -0.0471(8) -0.3496(13) 0.8858(5) 0.041(2) Uani 1 1 d . . . . .
O3A O 0.0450(7) -0.4380(14) 0.9603(5) 0.063(2) Uani 1 1 d . . . . .
C3B C 0.3666(6) 1.213(2) 0.5162(5) 0.0266(14) Uani 1 1 d . . . . .
C2A C 0.0344(7) 0.1973(18) 0.6843(5) 0.0256(16) Uani 1 1 d . . . . .
C1A C 0.0546(8) 0.3926(14) 0.6037(6) 0.0286(18) Uani 1 1 d . . . . .
C4A C 0.1119(8) -0.0516(16) 0.8460(6) 0.035(2) Uani 1 1 d . . . . .
H4A H 0.178833 -0.102486 0.909640 0.042 Uiso 1 1 calc R U . . .
C4B C 0.4346(8) 1.1205(13) 0.6331(6) 0.0261(17) Uani 1 1 d . . . . .
C6B C 0.6007(8) 1.1442(15) 0.8088(6) 0.037(2) Uani 1 1 d . . . . .
H6B H 0.673850 1.222810 0.859262 0.044 Uiso 1 1 calc R U . . .
C5A C -0.0162(8) -0.1567(15) 0.8166(6) 0.0294(18) Uani 1 1 d . . . . .
C6A C -0.1137(8) -0.0800(15) 0.7222(6) 0.0310(18) Uani 1 1 d . . . . .
H6A H -0.198649 -0.154011 0.702974 0.037 Uiso 1 1 calc R U . . .
C5B C 0.5447(7) 1.240(2) 0.7049(5) 0.0330(17) Uani 1 1 d . . . . .
H5B H 0.580199 1.384335 0.682893 0.040 Uiso 1 1 calc R U . . .
O2B O 0.6787(8) 0.9509(15) 1.0181(5) 0.072(2) Uani 1 1 d . . . . .
C7B C 0.5468(8) 0.9295(16) 0.8368(6) 0.0323(19) Uani 1 1 d . . . . .
C8B C 0.4378(8) 0.8147(15) 0.7621(6) 0.0326(19) Uani 1 1 d . . . . .
H8B H 0.402538 0.669385 0.783083 0.039 Uiso 1 1 calc R U . . .
C3A C 0.1368(8) 0.1319(15) 0.7772(6) 0.036(2) Uani 1 1 d . . . . .
H3A H 0.220893 0.208510 0.793846 0.043 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'
Mn Mn 0.3368 0.7283 '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 Mn1 N1A 95.4(2) . 2_556 ?
O1 Mn1 N1B 73.5(2) . . ?
O2 Mn1 O1 100.0(2) 1_545 . ?
O2 Mn1 N1A 89.6(2) 1_545 2_556 ?
O2 Mn1 N1B 91.4(2) 1_545 . ?
O2A Mn1 O1 83.7(2) 2_556 . ?
O2A Mn1 O2 163.11(19) 2_556 1_545 ?
O2A Mn1 N1A 73.6(2) 2_556 2_556 ?
O2A Mn1 N1B 105.4(2) 2_556 . ?
O1A Mn1 O1 159.4(2) . . ?
O1A Mn1 O2 89.3(2) . 1_545 ?
O1A Mn1 O2A 92.7(2) . 2_556 ?
O1A Mn1 N1A 103.1(2) . 2_556 ?
O1A Mn1 N1B 88.1(2) . . ?
N1A Mn1 N1B 168.8(2) 2_556 . ?
C3B O1 Mn1 118.0(5) . . ?
C3B O2 Mn1 124.3(5) . 1_565 ?
C1A O2A Mn1 119.6(5) . 2_546 ?
C1A O1A Mn1 123.1(5) . . ?
C2A N1A Mn1 113.4(5) . 2_546 ?
C6A N1A Mn1 126.8(5) . 2_546 ?
C6A N1A C2A 119.2(6) . . ?
C4B N1B Mn1 112.4(5) . . ?
C8B N1B Mn1 129.2(5) . . ?
C8B N1B C4B 117.5(7) . . ?
O1B N2B C7B 117.4(9) . . ?
O2B N2B O1B 124.5(10) . . ?
O2B N2B C7B 118.1(9) . . ?
O4A N2A C5A 117.5(7) . . ?
O3A N2A O4A 124.1(7) . . ?
O3A N2A C5A 118.4(8) . . ?
O1 C3B O2 127.1(7) . . ?
O1 C3B C4B 116.0(9) . . ?
O2 C3B C4B 116.9(7) . . ?
N1A C2A C1A 115.5(6) . . ?
N1A C2A C3A 123.1(7) . . ?
C3A C2A C1A 121.4(7) . . ?
O2A C1A C2A 116.9(7) . . ?
O1A C1A O2A 126.3(7) . . ?
O1A C1A C2A 116.8(6) . . ?
C5A C4A H4A 121.1 . . ?
C3A C4A H4A 121.1 . . ?
C3A C4A C5A 117.8(7) . . ?
N1B C4B C3B 114.6(7) . . ?
N1B C4B C5B 122.8(7) . . ?
C5B C4B C3B 122.6(7) . . ?
C5B C6B H6B 120.7 . . ?
C5B C6B C7B 118.5(8) . . ?
C7B C6B H6B 120.7 . . ?
C4A C5A N2A 119.9(7) . . ?
C6A C5A N2A 119.8(7) . . ?
C6A C5A C4A 120.3(7) . . ?
N1A C6A C5A 121.2(7) . . ?
N1A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C4B C5B H5B 120.6 . . ?
C6B C5B C4B 118.9(9) . . ?
C6B C5B H5B 120.6 . . ?
C6B C7B N2B 119.6(8) . . ?
C6B C7B C8B 120.6(7) . . ?
C8B C7B N2B 119.8(8) . . ?
N1B C8B C7B 121.7(7) . . ?
N1B C8B H8B 119.1 . . ?
C7B C8B H8B 119.1 . . ?
C2A C3A C4A 118.3(8) . . ?
C2A C3A H3A 120.9 . . ?
C4A C3A H3A 120.9 . . ?
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
Mn1 O1 2.174(5) . ?
Mn1 O2 2.173(5) 1_545 ?
Mn1 O2A 2.168(5) 2_556 ?
Mn1 O1A 2.150(5) . ?
Mn1 N1A 2.281(6) 2_556 ?
Mn1 N1B 2.294(6) . ?
O1 C3B 1.247(10) . ?
O2 C3B 1.254(11) . ?
O2A C1A 1.257(8) . ?
O1A C1A 1.247(9) . ?
N1A C2A 1.340(9) . ?
N1A C6A 1.319(9) . ?
N1B C4B 1.357(9) . ?
N1B C8B 1.339(8) . ?
O1B N2B 1.206(9) . ?
N2B O2B 1.201(10) . ?
N2B C7B 1.465(11) . ?
O4A N2A 1.232(9) . ?
N2A O3A 1.215(8) . ?
N2A C5A 1.452(9) . ?
C3B C4B 1.515(9) . ?
C2A C1A 1.520(10) . ?
C2A C3A 1.368(10) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.389(11) . ?
C4A C3A 1.388(11) . ?
C4B C5B 1.382(10) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.367(10) . ?
C6B C7B 1.368(11) . ?
C5A C6A 1.372(10) . ?
C6A H6A 0.9300 . ?
C5B H5B 0.9300 . ?
C7B C8B 1.377(10) . ?
C8B H8B 0.9300 . ?
C3A H3A 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
Mn1 O1 C3B O2 -152.0(6) . . . . ?
Mn1 O1 C3B C4B 26.9(8) . . . . ?
Mn1 O2 C3B O1 86.9(8) 1_565 . . . ?
Mn1 O2 C3B C4B -92.0(7) 1_565 . . . ?
Mn1 O2A C1A O1A 169.2(6) 2_546 . . . ?
Mn1 O2A C1A C2A -9.6(9) 2_546 . . . ?
Mn1 O1A C1A O2A -6.9(12) . . . . ?
Mn1 O1A C1A C2A 171.9(5) . . . . ?
Mn1 N1A C2A C1A 5.9(9) 2_546 . . . ?
Mn1 N1A C2A C3A -174.5(7) 2_546 . . . ?
Mn1 N1A C6A C5A 173.0(6) 2_546 . . . ?
Mn1 N1B C4B C3B 9.4(8) . . . . ?
Mn1 N1B C4B C5B -168.6(6) . . . . ?
Mn1 N1B C8B C7B 167.4(6) . . . . ?
O1 C3B C4B N1B -24.1(9) . . . . ?
O1 C3B C4B C5B 153.9(8) . . . . ?
O2 C3B C4B N1B 154.9(7) . . . . ?
O2 C3B C4B C5B -27.1(10) . . . . ?
N1A C2A C1A O2A 2.0(11) . . . . ?
N1A C2A C1A O1A -176.9(7) . . . . ?
N1A C2A C3A C4A 1.7(13) . . . . ?
N1B C4B C5B C6B -1.8(13) . . . . ?
O1B N2B C7B C6B -164.9(9) . . . . ?
O1B N2B C7B C8B 15.0(13) . . . . ?
N2B C7B C8B N1B -179.6(8) . . . . ?
O4A N2A C5A C4A 169.9(8) . . . . ?
O4A N2A C5A C6A -10.4(11) . . . . ?
N2A C5A C6A N1A 179.2(7) . . . . ?
O3A N2A C5A C4A -9.4(11) . . . . ?
O3A N2A C5A C6A 170.3(8) . . . . ?
C3B C4B C5B C6B -179.6(8) . . . . ?
C2A N1A C6A C5A 2.2(12) . . . . ?
C1A C2A C3A C4A -178.7(7) . . . . ?
C4A C5A C6A N1A -1.0(12) . . . . ?
C4B N1B C8B C7B -0.8(12) . . . . ?
C6B C7B C8B N1B 0.3(13) . . . . ?
C5A C4A C3A C2A -0.5(12) . . . . ?
C6A N1A C2A C1A 177.8(7) . . . . ?
C6A N1A C2A C3A -2.6(13) . . . . ?
C5B C6B C7B N2B 179.4(8) . . . . ?
C5B C6B C7B C8B -0.5(12) . . . . ?
O2B N2B C7B C6B 16.7(13) . . . . ?
O2B N2B C7B C8B -163.4(9) . . . . ?
C7B C6B C5B C4B 1.2(12) . . . . ?
C8B N1B C4B C3B 179.5(7) . . . . ?
C8B N1B C4B C5B 1.5(12) . . . . ?
C3A C2A C1A O2A -177.6(8) . . . . ?
C3A C2A C1A O1A 3.5(12) . . . . ?
C3A C4A C5A N2A 179.9(7) . . . . ?
C3A C4A C5A C6A 0.2(12) . . . . ?
