#------------------------------------------------------------------------------
#$Date: 2021-11-15 10:49:03 +0200 (Mon, 15 Nov 2021) $
#$Revision: 270646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/52/1565210.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_1565210
loop_
_publ_author_name
'Li, Xiao-Fei'
'Yang, Yan-Qiu'
'Li, Ya-Xue'
'Yang, Huai-Xia'
'Zhao, Wen-Feng'
'Meng, Xiang-Ru'
_publ_section_title
;
 Synthesis, crystal structure, and BSA binding studies of new Co(II) and
 Ni(II) complexes of 2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylate
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119469
_journal_paper_doi               10.1016/j.ica.2020.119469
_journal_volume                  505
_journal_year                    2020
_chemical_formula_moiety         'C12 H14 N4 Ni O12'
_chemical_formula_sum            'C12 H14 N4 Ni O12'
_chemical_formula_weight         464.98
_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   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.72(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5445(13)
_cell_length_b                   13.644(3)
_cell_length_c                   9.4681(19)
_cell_measurement_reflns_used    2509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9083
_cell_measurement_theta_min      2.6787
_cell_volume                     817.7(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2004)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5067
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.911
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.268
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2004)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_description       Prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0474
_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)+(0.0384P)²+0.9905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1711
_reflns_number_total             1941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-505-119469.cif
_cod_data_source_block           p2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1565210
_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_min   0.759
_shelx_estimated_absorpt_t_max   0.795
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
Ni1 Ni 0.000000 0.500000 0.000000 0.02353(16) Uani 1 2 d S . P . .
N1 N 0.0471(3) 0.41083(17) 0.1837(2) 0.0237(5) Uani 1 1 d . . . . .
N2 N 0.1185(4) 0.32980(17) 0.3910(2) 0.0255(5) Uani 1 1 d . . . . .
H2 H 0.181187 0.290861 0.459894 0.031 Uiso 1 1 calc R U . . .
O1 O -0.2545(3) 0.54408(16) 0.0749(2) 0.0294(5) Uani 1 1 d . . . . .
O2 O -0.4060(3) 0.52636(17) 0.2593(2) 0.0351(5) Uani 1 1 d . . . . .
O3 O -0.3136(3) 0.44107(17) 0.5096(2) 0.0359(5) Uani 1 1 d . . . . .
H3 H -0.341104 0.471649 0.432566 0.054 Uiso 1 1 calc R U . . .
O4 O -0.0659(4) 0.33902(17) 0.6259(2) 0.0376(5) Uani 1 1 d . . . . .
O5 O 0.1962(3) 0.60785(15) 0.1239(2) 0.0306(5) Uani 1 1 d . . . . .
H5B H 0.150042 0.621377 0.197849 0.046 Uiso 1 1 d R U . . .
H5A H 0.311922 0.576937 0.153669 0.046 Uiso 1 1 d R U . . .
O6 O 0.3633(3) 0.29406(16) 0.0860(2) 0.0341(5) Uani 1 1 d . . . . .
H6 H 0.358170 0.351909 0.061857 0.051 Uiso 1 1 d R U . . .
C1 C -0.2665(4) 0.5067(2) 0.1942(3) 0.0253(6) Uani 1 1 d . . . . .
C2 C -0.0998(4) 0.4351(2) 0.2593(3) 0.0245(6) Uani 1 1 d . . . . .
C3 C -0.0566(4) 0.3852(2) 0.3895(3) 0.0247(6) Uani 1 1 d . . . . .
C4 C -0.1467(4) 0.3857(2) 0.5173(3) 0.0286(6) Uani 1 1 d . . . . .
C5 C 0.1755(4) 0.3467(2) 0.2663(3) 0.0245(6) Uani 1 1 d . . . . .
C6 C 0.3634(4) 0.2962(2) 0.2356(3) 0.0312(7) Uani 1 1 d . . . . .
H6A H 0.490621 0.329077 0.289764 0.037 Uiso 1 1 calc R U . . .
H6B H 0.368260 0.229371 0.271257 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'
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'
Ni Ni 0.3393 1.1124 '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 Ni1 O1 180.0 3_565 .
O1 Ni1 N1 81.01(8) 3_565 3_565
O1 Ni1 N1 98.99(8) . 3_565
O1 Ni1 N1 98.99(8) 3_565 .
O1 Ni1 N1 81.01(8) . .
N1 Ni1 N1 180.0 3_565 .
O1 Ni1 O5 92.07(8) 3_565 3_565
O1 Ni1 O5 87.93(8) . 3_565
N1 Ni1 O5 90.16(9) 3_565 3_565
N1 Ni1 O5 89.84(9) . 3_565
O1 Ni1 O5 87.93(8) 3_565 .
O1 Ni1 O5 92.07(8) . .
N1 Ni1 O5 89.84(9) 3_565 .
N1 Ni1 O5 90.16(9) . .
O5 Ni1 O5 180.0 3_565 .
C5 N1 C2 105.9(2) . .
C5 N1 Ni1 144.90(19) . .
C2 N1 Ni1 108.62(17) . .
C5 N2 C3 108.2(2) . .
C5 N2 H2 125.9 . .
C3 N2 H2 125.9 . .
C1 O1 Ni1 115.52(17) . .
C4 O3 H3 109.5 . .
Ni1 O5 H5B 108.5 . .
Ni1 O5 H5A 101.8 . .
H5B O5 H5A 108.0 . .
C6 O6 H6 104.4 . .
O2 C1 O1 125.0(3) . .
O2 C1 C2 119.3(2) . .
O1 C1 C2 115.7(2) . .
C3 C2 N1 109.6(2) . .
C3 C2 C1 131.6(3) . .
N1 C2 C1 118.8(2) . .
N2 C3 C2 105.3(2) . .
N2 C3 C4 120.1(2) . .
C2 C3 C4 134.5(3) . .
O4 C4 O3 121.8(3) . .
O4 C4 C3 121.0(3) . .
O3 C4 C3 117.2(2) . .
N1 C5 N2 110.9(2) . .
N1 C5 C6 128.2(3) . .
N2 C5 C6 121.0(2) . .
O6 C6 C5 114.3(2) . .
O6 C6 H6A 108.7 . .
C5 C6 H6A 108.7 . .
O6 C6 H6B 108.7 . .
C5 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.0589(19) 3_565
Ni1 O1 2.0589(19) .
Ni1 N1 2.080(2) 3_565
Ni1 N1 2.080(2) .
Ni1 O5 2.104(2) 3_565
Ni1 O5 2.104(2) .
N1 C5 1.322(3) .
N1 C2 1.377(3) .
N2 C5 1.346(3) .
N2 C3 1.370(3) .
N2 H2 0.8600 .
O1 C1 1.260(3) .
O2 C1 1.254(3) .
O3 C4 1.315(3) .
O3 H3 0.8200 .
O4 C4 1.210(3) .
O5 H5B 0.8500 .
O5 H5A 0.8499 .
O6 C6 1.416(3) .
O6 H6 0.8201 .
C1 C2 1.477(4) .
C2 C3 1.373(4) .
C3 C4 1.475(4) .
C5 C6 1.501(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
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
_geom_hbond_publ_flag
O6 H6 O1 0.82 1.92 2.675(3) 151.6 3_565 yes
O3 H3 O2 0.82 1.75 2.571(3) 174.6 . yes
N2 H2 O6 0.86 1.86 2.707(3) 167.2 4_566 yes
O5 H5B O4 0.85 1.96 2.809(3) 174.7 3_566 yes
O5 H5A O2 0.85 1.99 2.821(3) 167.2 1_655 yes
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
Ni1 O1 C1 O2 177.9(2) . . . .
Ni1 O1 C1 C2 -1.7(3) . . . .
C5 N1 C2 C3 0.5(3) . . . .
Ni1 N1 C2 C3 -173.09(19) . . . .
C5 N1 C2 C1 179.8(2) . . . .
Ni1 N1 C2 C1 6.1(3) . . . .
O2 C1 C2 C3 -3.8(5) . . . .
O1 C1 C2 C3 175.8(3) . . . .
O2 C1 C2 N1 177.1(3) . . . .
O1 C1 C2 N1 -3.3(4) . . . .
C5 N2 C3 C2 0.0(3) . . . .
C5 N2 C3 C4 -176.4(2) . . . .
N1 C2 C3 N2 -0.3(3) . . . .
C1 C2 C3 N2 -179.4(3) . . . .
N1 C2 C3 C4 175.3(3) . . . .
C1 C2 C3 C4 -3.8(6) . . . .
N2 C3 C4 O4 1.4(4) . . . .
C2 C3 C4 O4 -173.7(3) . . . .
N2 C3 C4 O3 179.4(2) . . . .
C2 C3 C4 O3 4.3(5) . . . .
C2 N1 C5 N2 -0.5(3) . . . .
Ni1 N1 C5 N2 168.9(2) . . . .
C2 N1 C5 C6 179.8(3) . . . .
Ni1 N1 C5 C6 -10.8(5) . . . .
C3 N2 C5 N1 0.3(3) . . . .
C3 N2 C5 C6 -179.9(2) . . . .
N1 C5 C6 O6 -20.7(4) . . . .
N2 C5 C6 O6 159.6(3) . . . .
