#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/16/4301622.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_4301622
loop_
_publ_author_name
'Eugenio Coronado'
'Carlos Giménez-Saiz'
'Francisco M. Romero'
'Ana Tarazón'
_publ_section_title
;
Metal Complexes of a Picolinate-Based Nitronyl Nitroxide Free Radical
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2205
_journal_page_last               2214
_journal_paper_doi               10.1021/ic802218j
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         '(C26 H30 N6 O8 Mn), 3(H2 O)'
_chemical_formula_sum            'C26 H36 Mn N6 O11'
_chemical_formula_weight         663.55
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.52800(10)
_cell_length_b                   28.0110(5)
_cell_length_c                   14.0710(2)
_cell_measurement_reflns_used    9299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.998
_cell_volume                     2967.11(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20860
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.0047(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0697P)²+0.0110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                2152
_reflns_number_total             3369
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic802218j_si_002_4.cif
_cod_data_source_block           compound7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4301622
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.81769(6) 0.2500 0.2500 0.03919(18) Uani 1 2 d S . .
C1 C 0.7499(3) 0.22824(8) 0.45415(16) 0.0423(5) Uani 1 1 d . . .
C2 C 0.7566(3) 0.22768(9) 0.55247(17) 0.0521(6) Uani 1 1 d . . .
H2 H 0.7089 0.2021 0.5861 0.062 Uiso 1 1 calc R . .
C3 C 0.8337(3) 0.26496(10) 0.59988(18) 0.0527(6) Uani 1 1 d . . .
H3 H 0.8406 0.2646 0.6659 0.063 Uiso 1 1 calc R . .
C4 C 0.9013(3) 0.30312(8) 0.54940(15) 0.0455(6) Uani 1 1 d . . .
H4 H 0.9524 0.3290 0.5805 0.055 Uiso 1 1 calc R . .
C5 C 0.8908(3) 0.30186(7) 0.45111(14) 0.0368(5) Uani 1 1 d . . .
C6 C 0.9482(3) 0.34208(7) 0.39184(15) 0.0359(5) Uani 1 1 d . . .
C7 C 1.0561(3) 0.38837(7) 0.26304(15) 0.0374(5) Uani 1 1 d . . .
C8 C 0.9527(3) 0.42074(7) 0.33379(16) 0.0436(5) Uani 1 1 d . . .
C9 C 0.9990(3) 0.39369(8) 0.16018(16) 0.0530(6) Uani 1 1 d . . .
H9A H 1.0683 0.3727 0.1210 0.080 Uiso 1 1 calc R . .
H9B H 1.0170 0.4261 0.1401 0.080 Uiso 1 1 calc R . .
H9C H 0.8755 0.3857 0.1543 0.080 Uiso 1 1 calc R . .
C10 C 1.2574(3) 0.39145(9) 0.27206(17) 0.0505(6) Uani 1 1 d . . .
H10A H 1.2901 0.3903 0.3380 0.076 Uiso 1 1 calc R . .
H10B H 1.2982 0.4209 0.2449 0.076 Uiso 1 1 calc R . .
H10C H 1.3109 0.3651 0.2390 0.076 Uiso 1 1 calc R . .
C11 C 0.7613(3) 0.43030(10) 0.3042(2) 0.0631(7) Uani 1 1 d . . .
H11A H 0.7076 0.4011 0.2831 0.095 Uiso 1 1 calc R . .
H11B H 0.7596 0.4532 0.2534 0.095 Uiso 1 1 calc R . .
H11C H 0.6962 0.4427 0.3574 0.095 Uiso 1 1 calc R . .
C12 C 1.0484(4) 0.46625(8) 0.36234(19) 0.0606(7) Uani 1 1 d . . .
H12A H 0.9775 0.4835 0.4075 0.091 Uiso 1 1 calc R . .
H12B H 1.0675 0.4857 0.3071 0.091 Uiso 1 1 calc R . .
H12C H 1.1608 0.4583 0.3905 0.091 Uiso 1 1 calc R . .
C13 C 0.6609(3) 0.18918(9) 0.3965(2) 0.0500(6) Uani 1 1 d . . .
N1 N 0.8182(2) 0.26495(6) 0.40450(13) 0.0375(4) Uani 1 1 d . . .
N2 N 1.0047(2) 0.34005(6) 0.30163(12) 0.0341(4) Uani 1 1 d . . .
N3 N 0.9384(2) 0.38823(6) 0.41821(13) 0.0438(5) Uani 1 1 d . . .
O1 O 1.03497(18) 0.30119(5) 0.25409(9) 0.0374(4) Uani 1 1 d . . .
O2 O 0.8930(3) 0.40365(6) 0.49929(12) 0.0719(6) Uani 1 1 d . . .
O3 O 0.6570(2) 0.19562(6) 0.30711(13) 0.0550(5) Uani 1 1 d . . .
O4 O 0.5981(3) 0.15504(6) 0.44019(15) 0.0702(5) Uani 1 1 d . . .
O1W O 0.5136(3) 0.05583(8) 0.40505(18) 0.0850(7) Uani 1 1 d D . .
H1WA H 0.601(3) 0.0458(10) 0.436(2) 0.102 Uiso 1 1 d D . .
H1WB H 0.511(4) 0.0846(7) 0.417(3) 0.102 Uiso 1 1 d D . .
O2W O 0.7500 0.5000 -0.0084(3) 0.0886(10) Uani 1 2 d SD . .
H2W H 0.688(4) 0.5164(10) -0.0428(18) 0.106 Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
Mn Mn 0.3368 0.7283 '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
O3 Mn1 O3 109.84(9) 3 . ?
O3 Mn1 O1 88.00(6) 3 . ?
O3 Mn1 O1 154.01(6) . . ?
O3 Mn1 O1 154.01(6) 3 3 ?
O3 Mn1 O1 88.00(6) . 3 ?
O1 Mn1 O1 82.53(7) . 3 ?
O3 Mn1 N1 103.84(6) 3 . ?
O3 Mn1 N1 76.29(7) . . ?
O1 Mn1 N1 81.26(6) . . ?
O1 Mn1 N1 98.58(5) 3 . ?
O3 Mn1 N1 76.29(6) 3 3 ?
O3 Mn1 N1 103.84(6) . 3 ?
O1 Mn1 N1 98.58(5) . 3 ?
O1 Mn1 N1 81.26(6) 3 3 ?
N1 Mn1 N1 179.79(9) . 3 ?
N1 C1 C2 120.9(2) . . ?
N1 C1 C13 116.2(2) . . ?
C2 C1 C13 122.8(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 122.08(19) . . ?
N1 C5 C6 115.74(18) . . ?
C4 C5 C6 122.08(19) . . ?
N2 C6 N3 108.62(17) . . ?
N2 C6 C5 126.82(18) . . ?
N3 C6 C5 124.36(18) . . ?
N2 C7 C9 111.02(17) . . ?
N2 C7 C10 106.01(16) . . ?
C9 C7 C10 110.84(18) . . ?
N2 C7 C8 99.47(15) . . ?
C9 C7 C8 114.31(18) . . ?
C10 C7 C8 114.29(18) . . ?
N3 C8 C12 109.52(18) . . ?
N3 C8 C11 104.76(18) . . ?
C12 C8 C11 111.9(2) . . ?
N3 C8 C7 100.89(16) . . ?
C12 C8 C7 114.9(2) . . ?
C11 C8 C7 113.62(19) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O3 126.5(3) . . ?
O4 C13 C1 117.6(2) . . ?
O3 C13 C1 115.91(19) . . ?
C5 N1 C1 119.42(19) . . ?
C5 N1 Mn1 128.82(14) . . ?
C1 N1 Mn1 111.39(15) . . ?
O1 N2 C6 125.44(16) . . ?
O1 N2 C7 121.46(15) . . ?
C6 N2 C7 112.58(16) . . ?
O2 N3 C6 126.16(19) . . ?
O2 N3 C8 121.71(17) . . ?
C6 N3 C8 111.11(17) . . ?
N2 O1 Mn1 115.74(10) . . ?
C13 O3 Mn1 117.85(15) . . ?
H1WA O1W H1WB 104(2) . . ?
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 O3 2.1045(16) 3 ?
Mn1 O3 2.1046(16) . ?
Mn1 O1 2.1760(14) . ?
Mn1 O1 2.1760(14) 3 ?
Mn1 N1 2.2139(18) . ?
Mn1 N1 2.2139(18) 3 ?
C1 N1 1.345(3) . ?
C1 C2 1.384(3) . ?
C1 C13 1.517(3) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.341(3) . ?
C5 C6 1.467(3) . ?
C6 N2 1.340(3) . ?
C6 N3 1.347(2) . ?
C7 N2 1.509(2) . ?
C7 C9 1.517(3) . ?
C7 C10 1.524(3) . ?
C7 C8 1.555(3) . ?
C8 N3 1.501(3) . ?
C8 C12 1.518(3) . ?
C8 C11 1.523(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O4 1.231(3) . ?
C13 O3 1.271(3) . ?
N2 O1 1.298(2) . ?
N3 O2 1.267(2) . ?
O1W H1WA 0.838(17) . ?
O1W H1WB 0.823(18) . ?
O2W H2W 0.816(15) . ?
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
O1W H1WA O2W 0.838(17) 1.986(19) 2.780(3) 158(3) 3
O1W H1WB O4 0.823(18) 2.11(2) 2.893(3) 160(3) .
O2W H2W O1W 0.816(15) 2.013(12) 2.805(3) 163(3) 7_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139126495
