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#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/77/7057710.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_7057710
loop_
_publ_author_name
'Dimiza, Filitsa'
'Raptopoulou, Catherine P.'
'Psycharis, Vassilis'
'Papadopoulos, Athanasios N.'
'Psomas, George'
_publ_section_title
;
 Manganese(ii) complexes with the non-steroidal anti-inflammatory drugs
 naproxen and mefenamic acid: synthesis, structure, antioxidant capacity,
 and interaction with albumins and DNA
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16666
_journal_paper_doi               10.1039/C8NJ03226B
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C84 H88 Mn2 N8 O12'
_chemical_formula_weight         1511.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I -2b -2b'
_space_group_name_H-M_alt        'I c 2 a'
_symmetry_space_group_name_Hall  'I -2b -2b'
_symmetry_space_group_name_H-M   'I c 2 a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-06-26 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.43740(10)
_cell_length_b                   17.2488(3)
_cell_length_c                   29.1863(5)
_cell_measurement_reflns_used    20864
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      72.09
_cell_measurement_theta_min      7.16
_cell_volume                     3744.20(10)
_computing_cell_refinement       'Crystalclear, Rigaku MSC, 2005'
_computing_data_collection       'Crystalclear, Rigaku MSC, 2005'
_computing_data_reduction        'Crystalclear, Rigaku MSC, 2005'
_computing_molecular_graphics    'Diamond ver3.1'
_computing_publication_material  'publCIF, J.Appl.Cryst. 2010, 43, 920'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick,2008)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.915
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            22292
_diffrn_reflns_point_group_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.946
_diffrn_reflns_theta_min         7.159
_exptl_absorpt_coefficient_mu    3.303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Crystalclear, Rigaku MSC, 2005'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1588
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 899 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0422
_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)+(0.0464P)²+3.3599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.776
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                2371
_reflns_number_total             2871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj03226b2.cif
_cod_data_source_block           compound5
_cod_depositor_comments
'Adding full bibliography for 7057707--7057711.cif.'
_cod_database_code               7057710
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'-x, y+1/2, z'
'x, y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, y+1, -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
Mn1 Mn 1.0000 0.24681(9) 0.5000 0.0669(5) Uani 1 2 d S T P
N1 N 1.0929(7) 0.3491(3) 0.36613(15) 0.0592(15) Uani 1 1 d . . .
N2 N 1.1597(7) 0.3509(3) 0.52086(16) 0.0557(13) Uani 1 1 d . . .
O1 O 1.1117(6) 0.2438(3) 0.43253(10) 0.0619(11) Uani 1 1 d . . .
O2 O 1.3678(7) 0.1792(3) 0.43982(12) 0.0736(13) Uani 1 1 d . . .
O3 O 0.7984(14) 0.1632(4) 0.48271(17) 0.130(3) Uani 1 1 d . . .
C1 C 1.2618(8) 0.2205(3) 0.41714(16) 0.0482(14) Uani 1 1 d . . .
C2 C 1.3126(6) 0.2445(4) 0.36977(13) 0.0393(11) Uani 1 1 d . . .
C3 C 1.4471(8) 0.2027(4) 0.34813(17) 0.0491(14) Uani 1 1 d . . .
C4 C 1.4973(7) 0.2176(3) 0.30329(17) 0.0466(15) Uani 1 1 d . . .
C5 C 1.4110(7) 0.2774(3) 0.28007(16) 0.0456(14) Uani 1 1 d . . .
C6 C 1.2795(7) 0.3203(4) 0.30072(16) 0.0410(12) Uani 1 1 d . . .
C7 C 1.2253(7) 0.3048(3) 0.34578(15) 0.0392(12) Uani 1 1 d . . .
C8 C 0.9868(8) 0.4062(3) 0.34277(16) 0.0443(13) Uani 1 1 d . . .
C9 C 1.0530(7) 0.4802(4) 0.33639(16) 0.0452(14) Uani 1 1 d . . .
C10 C 0.9415(7) 0.5370(4) 0.31596(17) 0.0466(14) Uani 1 1 d . . .
C11 C 0.7711(9) 0.5164(4) 0.3022(2) 0.0584(17) Uani 1 1 d . . .
C12 C 0.7070(9) 0.4426(5) 0.3075(2) 0.069(2) Uani 1 1 d . . .
C13 C 0.8140(9) 0.3861(5) 0.3286(2) 0.0598(17) Uani 1 1 d . . .
C14 C 1.2397(8) 0.5013(5) 0.3496(3) 0.080(2) Uani 1 1 d . . .
H14A H 1.2366 0.5405 0.3738 0.121 Uiso 1 1 calc R U .
H14B H 1.3032 0.5221 0.3228 0.121 Uiso 1 1 calc R U .
H14C H 1.3026 0.4550 0.3607 0.121 Uiso 1 1 calc R U .
C15 C 1.0044(9) 0.6185(4) 0.3097(2) 0.0684(18) Uani 1 1 d . . .
H15A H 1.0400 0.6400 0.3395 0.103 Uiso 1 1 calc R U .
H15B H 0.9069 0.6497 0.2968 0.103 Uiso 1 1 calc R U .
H15C H 1.1077 0.6192 0.2889 0.103 Uiso 1 1 calc R U .
C21 C 1.0850(9) 0.4200(4) 0.5139(2) 0.0632(17) Uani 1 1 d . . .
C22 C 1.1609(13) 0.4866(5) 0.5323(4) 0.112(3) Uani 1 1 d . . .
H22 H 1.1059 0.5357 0.5277 0.157 Uiso 1 1 calc R U .
C23 C 1.3208(15) 0.4802(7) 0.5578(4) 0.115(3) Uani 1 1 d . . .
H23 H 1.3726 0.5248 0.5716 0.161 Uiso 1 1 calc R U .
C24 C 1.3999(15) 0.4103(8) 0.5625(3) 0.098(3) Uani 1 1 d . . .
C25 C 1.3161(11) 0.3471(6) 0.5445(3) 0.077(2) Uani 1 1 d . . .
C31 C 0.7746(16) 0.1192(7) 0.4447(3) 0.129(4) Uani 1 1 d . . .
H31A H 0.7614 0.0647 0.4536 0.193 Uiso 1 1 calc R U .
H31B H 0.8791 0.1249 0.4245 0.193 Uiso 1 1 calc R U .
H31C H 0.6661 0.1363 0.4285 0.193 Uiso 1 1 calc R U .
H1N H 1.056(8) 0.328(4) 0.391(2) 0.065(18) Uiso 1 1 d . . .
H3 H 1.499(7) 0.160(4) 0.366(2) 0.061(17) Uiso 1 1 d . . .
H4 H 1.592(8) 0.188(4) 0.287(2) 0.068(18) Uiso 1 1 d . . .
H5 H 1.446(6) 0.290(3) 0.2485(17) 0.032(12) Uiso 1 1 d . . .
H6 H 1.229(7) 0.361(4) 0.288(2) 0.052(17) Uiso 1 1 d . . .
H11 H 0.678(9) 0.555(5) 0.288(2) 0.09(2) Uiso 1 1 d . . .
H12 H 0.584(11) 0.424(5) 0.295(3) 0.11(3) Uiso 1 1 d . . .
H13 H 0.779(10) 0.335(5) 0.333(3) 0.09(2) Uiso 1 1 d . . .
H24 H 1.526(16) 0.398(7) 0.579(4) 0.15(4) Uiso 1 1 d . . .
H25 H 1.376(10) 0.291(5) 0.550(2) 0.08(2) Uiso 1 1 d . . .
H30 H 0.712(12) 0.173(6) 0.495(3) 0.11(3) Uiso 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 '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
O1 Mn1 O1 177.2(3) 2_756 .
O1 Mn1 O3 92.21(19) 2_756 2_756
O1 Mn1 O3 85.89(18) . 2_756
O1 Mn1 O3 85.90(18) 2_756 .
O1 Mn1 O3 92.21(19) . .
O3 Mn1 O3 95.3(6) 2_756 .
O1 Mn1 N2 88.59(17) 2_756 .
O1 Mn1 N2 93.66(18) . .
O3 Mn1 N2 96.0(3) 2_756 .
O3 Mn1 N2 167.6(3) . .
O1 Mn1 N2 93.67(18) 2_756 2_756
O1 Mn1 N2 88.59(17) . 2_756
O3 Mn1 N2 167.6(3) 2_756 2_756
O3 Mn1 N2 96.0(3) . 2_756
N2 Mn1 N2 73.3(3) . 2_756
C7 N1 C8 124.6(4) . .
C21 N2 C25 118.7(7) . .
C21 N2 Mn1 117.1(4) . .
C25 N2 Mn1 123.7(5) . .
C1 O1 Mn1 132.5(3) . .
C31 O3 Mn1 131.4(7) . .
O2 C1 O1 123.2(5) . .
O2 C1 C2 119.2(5) . .
O1 C1 C2 117.6(5) . .
C3 C2 C7 119.3(4) . .
C3 C2 C1 117.4(5) . .
C7 C2 C1 123.2(4) . .
C4 C3 C2 121.9(5) . .
C3 C4 C5 118.3(5) . .
C6 C5 C4 121.1(5) . .
C5 C6 C7 121.1(5) . .
N1 C7 C6 120.2(5) . .
N1 C7 C2 121.5(4) . .
C6 C7 C2 118.2(5) . .
C9 C8 C13 121.2(6) . .
C9 C8 N1 120.2(5) . .
C13 C8 N1 118.6(6) . .
C8 C9 C10 119.2(5) . .
C8 C9 C14 121.6(6) . .
C10 C9 C14 119.2(6) . .
C11 C10 C9 119.0(6) . .
C11 C10 C15 119.7(6) . .
C9 C10 C15 121.3(5) . .
C12 C11 C10 121.9(6) . .
C11 C12 C13 119.9(6) . .
C8 C13 C12 118.8(7) . .
N2 C21 C22 120.8(7) . .
N2 C21 C21 115.7(4) . 2_756
C22 C21 C21 123.5(5) . 2_756
C21 C22 C23 118.9(9) . .
C24 C23 C22 119.5(10) . .
C23 C24 C25 118.5(10) . .
N2 C25 C24 123.4(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O1 2.138(3) 2_756
Mn1 O1 2.138(3) .
Mn1 O3 2.141(7) 2_756
Mn1 O3 2.141(7) .
Mn1 N2 2.237(6) .
Mn1 N2 2.238(6) 2_756
N1 C7 1.380(7) .
N1 C8 1.434(7) .
N2 C21 1.331(8) .
N2 C25 1.354(10) .
O1 C1 1.269(6) .
O2 C1 1.252(7) .
O3 C31 1.354(9) .
C1 C2 1.492(6) .
C2 C3 1.385(8) .
C2 C7 1.412(7) .
C3 C4 1.385(7) .
C4 C5 1.391(7) .
C5 C6 1.366(8) .
C6 C7 1.401(7) .
C8 C9 1.381(8) .
C8 C13 1.394(9) .
C9 C10 1.414(7) .
C9 C14 1.486(8) .
C10 C11 1.376(8) .
C10 C15 1.493(9) .
C11 C12 1.368(10) .
C12 C13 1.401(10) .
C21 C22 1.387(11) .
C21 C21 1.503(13) 2_756
C22 C23 1.408(13) .
C23 C24 1.348(15) .
C24 C25 1.362(14) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22 O3 0.95 2.66 3.385(13) 133.8 3_755
C31 H31C O2 0.98 2.36 3.200(13) 143.2 1_455
N1 H1N O1 0.86(7) 1.93(7) 2.661(6) 141(6) .
O3 H30 O2 0.76(8) 1.99(9) 2.592(7) 137(9) 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139178836
