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#$Date: 2022-05-10 10:31:45 +0300 (Tue, 10 May 2022) $
#$Revision: 275288 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105194.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_8105194
loop_
_publ_author_name
'Liu, Xu'
'Meng, Xiang-Ru'
_publ_section_title
;
 Crystal structure of
 [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4
 N,N′,O,O′]nickel(II)] tetrahydrate,
 C16H12N4NiO10·4H2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              249
_journal_page_last               251
_journal_paper_doi               10.1515/ncrs-2021-0463
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C16 H12 N4 Ni O10, 4(H2 O)'
_chemical_formula_sum            'C16 H20 N4 Ni O14'
_chemical_formula_weight         551.07
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1945(2)
_cell_length_b                   16.1805(4)
_cell_length_c                   17.7912(5)
_cell_measurement_reflns_used    7723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      3.05
_cell_volume                     2071.08(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19289
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.518
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6828
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2457
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0353
_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)+(0.0478P)²+1.6460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2071
_reflns_number_total             2457
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0463_suppl.cif
_cod_data_source_block           exp_I
_cod_database_code               8105194
_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   0.814
_shelx_estimated_absorpt_t_max   0.862
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-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_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 0.85106(6) 0.750000 -0.02377(2) 0.02858(14) Uani 1 2 d S T P . .
O1 O 0.8891(3) 0.64733(10) -0.09459(9) 0.0380(4) Uani 1 1 d D . . . .
O2 O 0.8422(3) 0.51153(10) -0.09723(9) 0.0417(4) Uani 1 1 d . . . . .
O3 O 0.7149(3) 0.40744(10) -0.01041(10) 0.0411(4) Uani 1 1 d . . . . .
H3 H 0.761797 0.443422 -0.036739 0.062 Uiso 1 1 calc R U . . .
O4 O 0.5869(3) 0.40029(10) 0.10246(10) 0.0462(5) Uani 1 1 d . . . . .
O5 O 0.5726(4) 0.750000 -0.05902(15) 0.0439(6) Uani 1 2 d S T P . .
H5 H 0.525959 0.789800 -0.083862 0.066 Uiso 1 1 d R U . . .
O6 O 1.1317(4) 0.750000 -0.00514(17) 0.0472(6) Uani 1 2 d S T P . .
H6 H 1.190801 0.795420 -0.007356 0.071 Uiso 1 1 d R U . . .
O7 O 0.5062(3) 0.49183(12) 0.24964(10) 0.0512(5) Uani 1 1 d . . . . .
H7A H 0.568851 0.484683 0.289612 0.077 Uiso 1 1 d R U . . .
H7B H 0.477481 0.441742 0.241101 0.077 Uiso 1 1 d R U . . .
N1 N 0.7931(3) 0.65986(11) 0.05063(10) 0.0276(4) Uani 1 1 d . . . . .
N2 N 0.6759(3) 0.56915(11) 0.12886(10) 0.0288(4) Uani 1 1 d . . . . .
H2 H 0.629388 0.548025 0.169032 0.035 Uiso 1 1 calc R U . . .
C1 C 0.8400(3) 0.58154(14) -0.06440(13) 0.0316(5) Uani 1 1 d . . . . .
C2 C 0.7783(3) 0.58545(13) 0.01493(12) 0.0283(4) Uani 1 1 d . . . . .
C3 C 0.7058(3) 0.52823(13) 0.06308(12) 0.0286(4) Uani 1 1 d . . . . .
C4 C 0.6643(3) 0.43920(14) 0.05327(14) 0.0328(5) Uani 1 1 d . . . . .
C5 C 0.7319(3) 0.64909(13) 0.12055(12) 0.0272(4) Uani 1 1 d . . . . .
C6 C 0.7391(3) 0.70621(13) 0.18527(11) 0.0270(4) Uani 1 1 d . . . . .
C7 C 0.7506(3) 0.66589(14) 0.25481(12) 0.0350(5) Uani 1 1 d . . . . .
H7 H 0.755439 0.608457 0.255346 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7550(4) 0.70717(15) 0.32219(12) 0.0381(5) Uani 1 1 d . . . . .
H8 H 0.757917 0.678048 0.367237 0.046 Uiso 1 1 calc R U . . .
O8 O 0.451(3) 0.3117(7) 0.2578(7) 0.252(10) Uani 0.5 1 d . . P A 1
O8' O 0.3126(16) 0.3409(5) 0.2470(6) 0.129(3) Uani 0.5 1 d . . P B 2
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'
Ni Ni 0.3393 1.1124 '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 92.85(10) 7_575 . y
N1 Ni1 O6 95.63(8) 7_575 . y
N1 Ni1 O6 95.62(8) . . y
N1 Ni1 O5 89.92(8) 7_575 . y
N1 Ni1 O5 89.92(8) . . y
O6 Ni1 O5 171.94(12) . . y
N1 Ni1 O1 81.29(7) 7_575 7_575 y
N1 Ni1 O1 173.30(7) . 7_575 y
O6 Ni1 O1 88.20(7) . 7_575 y
O5 Ni1 O1 86.86(7) . 7_575 y
N1 Ni1 O1 173.30(7) 7_575 . y
N1 Ni1 O1 81.29(7) . . y
O6 Ni1 O1 88.20(7) . . y
O5 Ni1 O1 86.86(7) . . y
O1 Ni1 O1 104.37(9) 7_575 . y
C1 O1 Ni1 112.36(14) . . ?
C4 O3 H3 109.5 . . ?
Ni1 O5 H5 122.1 . . ?
Ni1 O5 H5 122.13(3) . 7_575 ?
H5 O5 H5 98.5 . 7_575 ?
Ni1 O6 H6 119.1 . . ?
Ni1 O6 H6 119.087(13) . 7_575 ?
H6 O6 H6 119.7 . 7_575 ?
H7A O7 H7B 98.5 . . ?
C5 N1 C2 107.08(18) . . ?
C5 N1 Ni1 141.06(15) . . ?
C2 N1 Ni1 110.43(13) . . ?
C3 N2 C5 108.76(18) . . ?
C3 N2 H2 125.6 . . ?
C5 N2 H2 125.6 . . ?
O1 C1 O2 124.0(2) . . ?
O1 C1 C2 117.40(19) . . ?
O2 C1 C2 118.6(2) . . ?
C3 C2 N1 109.62(18) . . ?
C3 C2 C1 133.1(2) . . ?
N1 C2 C1 117.25(19) . . ?
N2 C3 C2 105.66(18) . . ?
N2 C3 C4 122.8(2) . . ?
C2 C3 C4 131.5(2) . . ?
O4 C4 O3 123.6(2) . . ?
O4 C4 C3 120.8(2) . . ?
O3 C4 C3 115.6(2) . . ?
N1 C5 N2 108.87(18) . . ?
N1 C5 C6 129.41(19) . . ?
N2 C5 C6 121.31(18) . . ?
C7 C6 C6 117.76(13) . 7_575 ?
C7 C6 C5 113.51(19) . . ?
C6 C6 C5 128.72(11) 7_575 . ?
C8 C7 C6 123.1(2) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 C8 119.12(14) . 7_575 ?
C7 C8 H8 120.4 . . ?
C8 C8 H8 120.4 7_575 . ?
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 2.0133(18) 7_575 y
Ni1 N1 2.0133(18) . y
Ni1 O6 2.046(3) . y
Ni1 O5 2.099(3) . y
Ni1 O1 2.1028(16) 7_575 y
Ni1 O1 2.1029(16) . y
O1 C1 1.244(3) . ?
O2 C1 1.275(3) . ?
O3 C4 1.296(3) . ?
O3 H3 0.8200 . ?
O4 C4 1.213(3) . ?
O5 H5 0.8500 . ?
O5 H5 0.8500 7_575 ?
O6 H6 0.8500 . ?
O6 H6 0.8499 7_575 ?
O7 H7A 0.8499 . ?
O7 H7B 0.8501 . ?
N1 C5 1.331(3) . ?
N1 C2 1.365(3) . ?
N2 C3 1.362(3) . ?
N2 C5 1.363(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.481(3) . ?
C2 C3 1.365(3) . ?
C3 C4 1.481(3) . ?
C5 C6 1.478(3) . ?
C6 C7 1.401(3) . ?
C6 C6 1.417(4) 7_575 ?
C7 C8 1.373(3) . ?
C7 H7 0.9300 . ?
C8 C8 1.386(5) 7_575 ?
C8 H8 0.9300 . ?
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
O3 H3 O2 0.82 1.65 2.462(2) 173.7 . yes
O5 H5 O4 0.85 1.99 2.798(2) 158.1 3_655 yes
O6 H6 O3 0.85 1.96 2.790(2) 164.7 3_755 yes
O7 H7A O2 0.85 2.11 2.935(3) 162.5 2_665 yes
O7 H7B O8'^b 0.85 2.02 2.812(10) 154.6 . yes
N2 H2 O7 0.86 1.92 2.770(3) 172.3 . 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 176.88(19) . . . .
Ni1 O1 C1 C2 -4.2(3) . . . .
C5 N1 C2 C3 0.5(3) . . . .
Ni1 N1 C2 C3 -168.83(15) . . . .
C5 N1 C2 C1 -179.57(19) . . . .
Ni1 N1 C2 C1 11.1(2) . . . .
O1 C1 C2 C3 175.2(2) . . . .
O2 C1 C2 C3 -5.8(4) . . . .
O1 C1 C2 N1 -4.7(3) . . . .
O2 C1 C2 N1 174.3(2) . . . .
C5 N2 C3 C2 -0.8(2) . . . .
C5 N2 C3 C4 178.5(2) . . . .
N1 C2 C3 N2 0.2(2) . . . .
C1 C2 C3 N2 -179.7(2) . . . .
N1 C2 C3 C4 -179.0(2) . . . .
C1 C2 C3 C4 1.0(4) . . . .
N2 C3 C4 O4 6.1(3) . . . .
C2 C3 C4 O4 -174.8(2) . . . .
N2 C3 C4 O3 -174.4(2) . . . .
C2 C3 C4 O3 4.8(4) . . . .
C2 N1 C5 N2 -1.0(2) . . . .
Ni1 N1 C5 N2 162.98(18) . . . .
C2 N1 C5 C6 171.5(2) . . . .
Ni1 N1 C5 C6 -24.5(4) . . . .
C3 N2 C5 N1 1.2(2) . . . .
C3 N2 C5 C6 -172.10(19) . . . .
N1 C5 C6 C7 -150.0(2) . . . .
N2 C5 C6 C7 21.7(3) . . . .
N1 C5 C6 C6 28.8(3) . . . 7_575
N2 C5 C6 C6 -159.45(13) . . . 7_575
C6 C6 C7 C8 2.4(3) 7_575 . . .
C5 C6 C7 C8 -178.6(2) . . . .
C6 C7 C8 C8 -2.4(3) . . . 7_575
