#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/16/4301619.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_4301619
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 Ni O8), 3(H2 O)'
_chemical_formula_sum            'C26 H36 N6 Ni O11'
_chemical_formula_weight         667.32
_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                   7.51620(10)
_cell_length_b                   27.7143(4)
_cell_length_c                   13.7502(2)
_cell_measurement_reflns_used    3733
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2864.25(7)
_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      180(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6107
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0372
_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)+(0.0507P)²+0.2043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                2182
_reflns_number_total             3285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic802218j_si_002_1.cif
_cod_data_source_block           compound4
_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               4301619
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
Ni1 Ni 0.81270(5) 0.2500 0.2500 0.02290(13) Uani 1 2 d S . .
C1 C 0.7360(3) 0.22451(7) 0.44319(14) 0.0257(5) Uani 1 1 d . . .
C2 C 0.7367(3) 0.22234(8) 0.54361(15) 0.0309(5) Uani 1 1 d . . .
H2 H 0.6844 0.1958 0.5765 0.037 Uiso 1 1 calc R . .
C3 C 0.8148(3) 0.25946(8) 0.59536(16) 0.0319(5) Uani 1 1 d . . .
H3 H 0.8182 0.2584 0.6644 0.038 Uiso 1 1 calc R . .
C4 C 0.8882(3) 0.29838(8) 0.54609(14) 0.0289(5) Uani 1 1 d . . .
H4 H 0.9406 0.3244 0.5806 0.035 Uiso 1 1 calc R . .
C5 C 0.8830(3) 0.29834(7) 0.44480(14) 0.0241(5) Uani 1 1 d . . .
C6 C 0.9436(3) 0.33954(7) 0.38700(14) 0.0243(5) Uani 1 1 d . . .
C7 C 1.0509(3) 0.38833(7) 0.25844(14) 0.0245(5) Uani 1 1 d . . .
C8 C 0.9516(3) 0.42008(7) 0.33394(14) 0.0287(5) Uani 1 1 d . . .
C9 C 0.9921(3) 0.39682(8) 0.15368(14) 0.0344(5) Uani 1 1 d . . .
H9A H 1.0573 0.3750 0.1104 0.052 Uiso 1 1 calc R . .
H9B H 1.0170 0.4303 0.1354 0.052 Uiso 1 1 calc R . .
H9C H 0.8641 0.3906 0.1479 0.052 Uiso 1 1 calc R . .
C10 C 1.2524(3) 0.38951(8) 0.26661(15) 0.0324(5) Uani 1 1 d . . .
H10A H 1.2868 0.3873 0.3352 0.049 Uiso 1 1 calc R . .
H10B H 1.2973 0.4198 0.2392 0.049 Uiso 1 1 calc R . .
H10C H 1.3030 0.3622 0.2307 0.049 Uiso 1 1 calc R . .
C11 C 0.7587(3) 0.43083(9) 0.30635(17) 0.0399(6) Uani 1 1 d . . .
H11A H 0.7001 0.4009 0.2858 0.060 Uiso 1 1 calc R . .
H11B H 0.7562 0.4542 0.2529 0.060 Uiso 1 1 calc R . .
H11C H 0.6961 0.4443 0.3627 0.060 Uiso 1 1 calc R . .
C12 C 1.0507(3) 0.46528(7) 0.36403(16) 0.0372(6) Uani 1 1 d . . .
H12A H 0.9808 0.4828 0.4127 0.056 Uiso 1 1 calc R . .
H12B H 1.0692 0.4859 0.3070 0.056 Uiso 1 1 calc R . .
H12C H 1.1662 0.4564 0.3918 0.056 Uiso 1 1 calc R . .
C13 C 0.6451(3) 0.18677(8) 0.37929(16) 0.0302(5) Uani 1 1 d . . .
N1 N 0.8109(2) 0.26145(6) 0.39486(12) 0.0232(4) Uani 1 1 d . . .
N2 N 0.9938(2) 0.33895(6) 0.29356(11) 0.0239(4) Uani 1 1 d . . .
N3 N 0.9398(2) 0.38590(6) 0.41807(12) 0.0283(4) Uani 1 1 d . . .
O1 O 1.01711(18) 0.30062(5) 0.24107(9) 0.0241(3) Uani 1 1 d . . .
O2 O 0.9010(2) 0.40047(6) 0.50309(11) 0.0459(4) Uani 1 1 d . . .
O3 O 0.64374(19) 0.19600(5) 0.28815(11) 0.0316(3) Uani 1 1 d . . .
O4 O 0.5767(2) 0.15175(5) 0.42042(11) 0.0392(4) Uani 1 1 d . . .
O1W O 0.5067(3) 0.05143(6) 0.39693(14) 0.0477(5) Uani 1 1 d D . .
H1WA H 0.590(3) 0.0391(8) 0.4253(18) 0.057 Uiso 1 1 d D . .
H1WB H 0.513(4) 0.0804(6) 0.3991(19) 0.057 Uiso 1 1 d D . .
O2W O 0.7500 0.5000 -0.00391(18) 0.0453(6) Uani 1 2 d SD . .
H2W H 0.687(3) 0.5166(8) -0.0380(12) 0.054 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
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
N1 Ni1 N1 179.22(9) 3 . ?
N1 Ni1 O3 81.76(6) 3 3 ?
N1 Ni1 O3 97.75(6) . 3 ?
N1 Ni1 O3 97.75(6) 3 . ?
N1 Ni1 O3 81.76(6) . . ?
O3 Ni1 O3 102.62(9) 3 . ?
N1 Ni1 O1 93.02(6) 3 . ?
N1 Ni1 O1 87.56(6) . . ?
O3 Ni1 O1 87.12(6) 3 . ?
O3 Ni1 O1 166.37(5) . . ?
N1 Ni1 O1 87.56(6) 3 3 ?
N1 Ni1 O1 93.02(6) . 3 ?
O3 Ni1 O1 166.37(5) 3 3 ?
O3 Ni1 O1 87.12(6) . 3 ?
O1 Ni1 O1 85.02(8) . 3 ?
N1 C1 C2 121.7(2) . . ?
N1 C1 C13 115.11(18) . . ?
C2 C1 C13 123.1(2) . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 121.45(19) . . ?
N1 C5 C6 116.16(17) . . ?
C4 C5 C6 122.25(19) . . ?
N2 C6 N3 108.68(17) . . ?
N2 C6 C5 126.80(17) . . ?
N3 C6 C5 124.20(18) . . ?
N2 C7 C10 106.17(16) . . ?
N2 C7 C9 111.02(17) . . ?
C10 C7 C9 110.82(17) . . ?
N2 C7 C8 99.38(15) . . ?
C10 C7 C8 114.69(17) . . ?
C9 C7 C8 113.89(17) . . ?
N3 C8 C12 109.94(16) . . ?
N3 C8 C11 105.01(17) . . ?
C12 C8 C11 111.91(19) . . ?
N3 C8 C7 100.75(15) . . ?
C12 C8 C7 114.53(18) . . ?
C11 C8 C7 113.62(18) . . ?
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 127.1(2) . . ?
O4 C13 C1 117.44(19) . . ?
O3 C13 C1 115.47(18) . . ?
C1 N1 C5 119.68(17) . . ?
C1 N1 Ni1 111.80(13) . . ?
C5 N1 Ni1 128.36(13) . . ?
O1 N2 C6 125.62(16) . . ?
O1 N2 C7 121.67(14) . . ?
C6 N2 C7 112.02(15) . . ?
O2 N3 C6 126.62(17) . . ?
O2 N3 C8 121.54(16) . . ?
C6 N3 C8 110.80(16) . . ?
N2 O1 Ni1 114.78(11) . . ?
C13 O3 Ni1 113.30(13) . . ?
H1WA O1W H1WB 111(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
Ni1 N1 2.0169(17) 3 ?
Ni1 N1 2.0169(17) . ?
Ni1 O3 2.0315(14) 3 ?
Ni1 O3 2.0315(14) . ?
Ni1 O1 2.0842(14) . ?
Ni1 O1 2.0842(14) 3 ?
C1 N1 1.344(3) . ?
C1 C2 1.382(3) . ?
C1 C13 1.527(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.346(3) . ?
C5 C6 1.464(3) . ?
C6 N2 1.339(3) . ?
C6 N3 1.354(2) . ?
C7 N2 1.513(2) . ?
C7 C10 1.519(3) . ?
C7 C9 1.525(3) . ?
C7 C8 1.552(3) . ?
C8 N3 1.498(3) . ?
C8 C12 1.515(3) . ?
C8 C11 1.528(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O4 1.235(2) . ?
C13 O3 1.279(3) . ?
N2 O1 1.296(2) . ?
N3 O2 1.271(2) . ?
O1W H1WA 0.810(16) . ?
O1W H1WB 0.804(16) . ?
O2W H2W 0.812(9) . ?
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 0.810(16) 1.948(16) 2.746(2) 168(3) 3
O1W H1WB O4 0.804(16) 2.057(18) 2.848(2) 168(3) .
O2W H2W O1W 0.812(9) 1.960(9) 2.759(2) 168(2) 7_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139126491
