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#$Date: 2022-10-24 11:43:03 +0300 (Mon, 24 Oct 2022) $
#$Revision: 278737 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105957.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.
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data_8105957
loop_
_publ_author_name
'Wang, Wen-Bin'
'Shi, Xin-Chang'
'Li, Ying-Ying'
'Cheng, Fang-Rong'
_publ_section_title
;
 Crystal structure of
 [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′]
 zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1133
_journal_page_last               1135
_journal_paper_doi               10.1515/ncrs-2019-0201
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 N4 O9 Zn, H2 O'
_chemical_formula_sum            'C16 H12 N4 O10 Zn'
_chemical_formula_weight         485.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.481(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6618(10)
_cell_length_b                   13.5466(6)
_cell_length_c                   14.7722(8)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.30
_cell_volume                     3541.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker D8 VENTURE'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            42976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_min         2.600
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6744
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.080
_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     282
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0392
_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)+(0.0370P)²+14.5205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3574
_reflns_number_total             4093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0201_suppl.cif
_cod_data_source_block           exp_I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8105957
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
Zn1 Zn 0.26353(2) 0.40295(2) 0.61820(2) 0.02618(11) Uani 1 1 d . . . . .
N1 N 0.17752(12) 0.49997(16) 0.61009(16) 0.0229(5) Uani 1 1 d . . . . .
N2 N 0.09564(12) 0.60807(16) 0.62725(17) 0.0236(5) Uani 1 1 d . . . . .
H2A H 0.0755 0.6636 0.6338 0.028 Uiso 1 1 calc R U . . .
N3 N 0.33460(12) 0.50341(16) 0.70891(16) 0.0229(5) Uani 1 1 d . . . . .
N4 N 0.40837(13) 0.61456(16) 0.80055(17) 0.0254(5) Uani 1 1 d . . . . .
H4A H 0.4256 0.6708 0.8248 0.030 Uiso 1 1 calc R U . . .
O1 O -0.05281(14) 0.5780(2) 0.6315(2) 0.0538(7) Uani 1 1 d . . . . .
O2 O -0.04201(13) 0.41642(19) 0.6188(2) 0.0504(7) Uani 1 1 d . . . . .
H2 H -0.0110 0.3780 0.6096 0.076 Uiso 1 1 calc R U . . .
O3 O 0.05557(12) 0.29507(16) 0.60126(19) 0.0418(6) Uani 1 1 d . . . . .
O4 O 0.17496(12) 0.30331(15) 0.60113(18) 0.0386(5) Uani 1 1 d . . . . .
O5 O 0.34051(12) 0.30747(14) 0.70750(16) 0.0330(5) Uani 1 1 d . . . . .
O6 O 0.44839(11) 0.30101(15) 0.82917(16) 0.0323(5) Uani 1 1 d . . . . .
O7 O 0.54398(12) 0.42806(17) 0.92638(18) 0.0396(5) Uani 1 1 d . . . . .
H7 H 0.5140 0.3875 0.8942 0.059 Uiso 1 1 calc R U . . .
O8 O 0.55500(14) 0.59070(18) 0.9314(2) 0.0494(7) Uani 1 1 d . . . . .
O9 O 0.29424(14) 0.3982(2) 0.50384(18) 0.0493(7) Uani 1 1 d . . . . .
H1W H 0.2557 0.3943 0.4543 0.074 Uiso 1 1 d R U . . .
H2W H 0.3376 0.3832 0.5007 0.074 Uiso 1 1 d R U . . .
O10 O 0.19090(13) 0.38664(16) 0.34254(17) 0.0386(5) Uani 1 1 d . . . . .
H3W H 0.1818 0.3277 0.3223 0.058 Uiso 1 1 d R U . . .
H4W H 0.1471 0.4031 0.3431 0.058 Uiso 1 1 d R U . . .
C1 C -0.01589(17) 0.5065(2) 0.6241(2) 0.0340(7) Uani 1 1 d . . . . .
C2 C 0.06170(15) 0.5178(2) 0.6197(2) 0.0242(5) Uani 1 1 d . . . . .
C3 C 0.11336(15) 0.4515(2) 0.6089(2) 0.0241(5) Uani 1 1 d . . . . .
C4 C 0.11433(16) 0.3419(2) 0.6020(2) 0.0301(6) Uani 1 1 d . . . . .
C5 C 0.16644(14) 0.59517(19) 0.62259(19) 0.0209(5) Uani 1 1 d . . . . .
C6 C 0.21735(14) 0.67894(19) 0.62585(19) 0.0217(5) Uani 1 1 d . . . . .
C7 C 0.18184(15) 0.7633(2) 0.5775(2) 0.0262(6) Uani 1 1 d . . . . .
H7A H 0.1306 0.7608 0.5435 0.031 Uiso 1 1 calc R U . . .
C8 C 0.22075(17) 0.8503(2) 0.5790(2) 0.0326(7) Uani 1 1 d . . . . .
H8A H 0.1956 0.9062 0.5484 0.039 Uiso 1 1 calc R U . . .
C9 C 0.29751(18) 0.8530(2) 0.6264(2) 0.0341(7) Uani 1 1 d . . . . .
H9A H 0.3244 0.9111 0.6279 0.041 Uiso 1 1 calc R U . . .
C10 C 0.33424(16) 0.7697(2) 0.6714(2) 0.0291(6) Uani 1 1 d . . . . .
H10A H 0.3862 0.7723 0.7011 0.035 Uiso 1 1 calc R U . . .
C11 C 0.29624(14) 0.68111(19) 0.67434(19) 0.0217(5) Uani 1 1 d . . . . .
C12 C 0.34270(15) 0.59950(19) 0.72693(19) 0.0225(5) Uani 1 1 d . . . . .
C13 C 0.39594(15) 0.3471(2) 0.7698(2) 0.0250(6) Uani 1 1 d . . . . .
C14 C 0.39483(15) 0.45662(19) 0.77235(19) 0.0231(5) Uani 1 1 d . . . . .
C15 C 0.44198(15) 0.5250(2) 0.8289(2) 0.0242(5) Uani 1 1 d . . . . .
C16 C 0.51822(16) 0.5181(2) 0.9007(2) 0.0293(6) Uani 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 0.0033 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'
Zn Zn 0.2839 1.4301 '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
O9 Zn1 N1 114.26(10) . .
O9 Zn1 O5 101.33(10) . .
N1 Zn1 O5 144.26(9) . .
O9 Zn1 N3 106.20(10) . .
N1 Zn1 N3 86.87(9) . .
O5 Zn1 N3 79.93(8) . .
O9 Zn1 O4 108.24(11) . .
N1 Zn1 O4 80.33(9) . .
O5 Zn1 O4 92.06(8) . .
N3 Zn1 O4 145.54(10) . .
C5 N1 C3 107.2(2) . .
C5 N1 Zn1 140.21(18) . .
C3 N1 Zn1 111.14(17) . .
C5 N2 C2 108.4(2) . .
C5 N2 H2A 125.8 . .
C2 N2 H2A 125.8 . .
C12 N3 C14 107.5(2) . .
C12 N3 Zn1 141.60(19) . .
C14 N3 Zn1 110.94(17) . .
C15 N4 C12 108.6(2) . .
C15 N4 H4A 125.7 . .
C12 N4 H4A 125.7 . .
C1 O2 H2 109.5 . .
C4 O4 Zn1 114.41(18) . .
C13 O5 Zn1 116.17(17) . .
C16 O7 H7 109.5 . .
Zn1 O9 H1W 110.4 . .
Zn1 O9 H2W 127.1 . .
H1W O9 H2W 119.9 . .
H3W O10 H4W 99.5 . .
O1 C1 O2 122.7(3) . .
O1 C1 C2 120.9(3) . .
O2 C1 C2 116.5(3) . .
N2 C2 C3 105.8(2) . .
N2 C2 C1 121.7(3) . .
C3 C2 C1 132.5(3) . .
N1 C3 C2 109.4(2) . .
N1 C3 C4 116.9(2) . .
C2 C3 C4 133.6(3) . .
O4 C4 O3 125.2(3) . .
O4 C4 C3 116.6(2) . .
O3 C4 C3 118.2(3) . .
N1 C5 N2 109.2(2) . .
N1 C5 C6 128.8(2) . .
N2 C5 C6 121.9(2) . .
C7 C6 C11 119.3(2) . .
C7 C6 C5 114.7(2) . .
C11 C6 C5 126.1(2) . .
C8 C7 C6 121.9(3) . .
C8 C7 H7A 119.1 . .
C6 C7 H7A 119.1 . .
C9 C8 C7 119.1(3) . .
C9 C8 H8A 120.4 . .
C7 C8 H8A 120.4 . .
C10 C9 C8 120.0(3) . .
C10 C9 H9A 120.0 . .
C8 C9 H9A 120.0 . .
C9 C10 C11 122.5(3) . .
C9 C10 H10A 118.7 . .
C11 C10 H10A 118.7 . .
C10 C11 C6 117.2(2) . .
C10 C11 C12 116.2(2) . .
C6 C11 C12 126.6(2) . .
N3 C12 N4 108.7(2) . .
N3 C12 C11 128.5(2) . .
N4 C12 C11 122.5(2) . .
O6 C13 O5 125.0(3) . .
O6 C13 C14 119.6(2) . .
O5 C13 C14 115.3(2) . .
C15 C14 N3 109.6(2) . .
C15 C14 C13 133.0(2) . .
N3 C14 C13 117.4(2) . .
C14 C15 N4 105.7(2) . .
C14 C15 C16 132.9(3) . .
N4 C15 C16 121.1(2) . .
O8 C16 O7 122.3(3) . .
O8 C16 C15 121.5(3) . .
O7 C16 C15 116.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O9 1.949(3) .
Zn1 N1 2.048(2) .
Zn1 O5 2.068(2) .
Zn1 N3 2.069(2) .
Zn1 O4 2.087(2) .
N1 C5 1.328(3) .
N1 C3 1.361(3) .
N2 C5 1.356(3) .
N2 C2 1.365(3) .
N2 H2A 0.8600 .
N3 C12 1.328(3) .
N3 C14 1.369(3) .
N4 C15 1.369(3) .
N4 C12 1.372(3) .
N4 H4A 0.8600 .
O1 C1 1.214(4) .
O2 C1 1.307(4) .
O2 H2 0.8200 .
O3 C4 1.264(4) .
O4 C4 1.250(4) .
O5 C13 1.266(3) .
O6 C13 1.254(3) .
O7 C16 1.322(4) .
O7 H7 0.8200 .
O8 C16 1.203(4) .
O9 H1W 0.8500 .
O9 H2W 0.8499 .
O10 H3W 0.8500 .
O10 H4W 0.8500 .
C1 C2 1.478(4) .
C2 C3 1.364(4) .
C3 C4 1.488(4) .
C5 C6 1.471(3) .
C6 C7 1.398(4) .
C6 C11 1.419(3) .
C7 C8 1.380(4) .
C7 H7A 0.9300 .
C8 C9 1.381(4) .
C8 H8A 0.9300 .
C9 C10 1.378(4) .
C9 H9A 0.9300 .
C10 C11 1.401(4) .
C10 H10A 0.9300 .
C11 C12 1.466(4) .
C13 C14 1.484(4) .
C14 C15 1.366(4) .
C15 C16 1.483(4) .
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
O2 H2 O3 0.82 1.71 2.527(4) 174.8 .
O7 H7 O6 0.82 1.75 2.566(3) 177.8 .
O9 H1W O10 0.85 1.71 2.551(3) 168.7 .
N2 H2A O6 0.86 2.03 2.873(3) 167.0 4_556
N4 H4A O3 0.86 1.98 2.814(3) 164.3 4_556
O9 H2W O7 0.85 2.21 2.893(3) 136.7 2_656
O10 H3W O5 0.85 1.90 2.744(3) 172.6 7_556
O10 H4W O1 0.85 1.93 2.765(3) 167.5 5_566
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
C5 N2 C2 C3 -1.0(3) . . . .
C5 N2 C2 C1 178.8(3) . . . .
O1 C1 C2 N2 2.5(5) . . . .
O2 C1 C2 N2 -178.2(3) . . . .
O1 C1 C2 C3 -177.8(3) . . . .
O2 C1 C2 C3 1.5(5) . . . .
C5 N1 C3 C2 0.7(3) . . . .
Zn1 N1 C3 C2 169.85(18) . . . .
C5 N1 C3 C4 -176.1(2) . . . .
Zn1 N1 C3 C4 -6.9(3) . . . .
N2 C2 C3 N1 0.2(3) . . . .
C1 C2 C3 N1 -179.6(3) . . . .
N2 C2 C3 C4 176.2(3) . . . .
C1 C2 C3 C4 -3.6(6) . . . .
Zn1 O4 C4 O3 -173.5(3) . . . .
Zn1 O4 C4 C3 3.6(4) . . . .
N1 C3 C4 O4 2.3(4) . . . .
C2 C3 C4 O4 -173.5(3) . . . .
N1 C3 C4 O3 179.7(3) . . . .
C2 C3 C4 O3 3.9(5) . . . .
C3 N1 C5 N2 -1.3(3) . . . .
Zn1 N1 C5 N2 -165.4(2) . . . .
C3 N1 C5 C6 -177.8(3) . . . .
Zn1 N1 C5 C6 18.1(5) . . . .
C2 N2 C5 N1 1.5(3) . . . .
C2 N2 C5 C6 178.2(2) . . . .
N1 C5 C6 C7 138.5(3) . . . .
N2 C5 C6 C7 -37.5(4) . . . .
N1 C5 C6 C11 -43.1(4) . . . .
N2 C5 C6 C11 140.9(3) . . . .
C11 C6 C7 C8 -2.8(4) . . . .
C5 C6 C7 C8 175.7(3) . . . .
C6 C7 C8 C9 2.5(5) . . . .
C7 C8 C9 C10 0.0(5) . . . .
C8 C9 C10 C11 -2.2(5) . . . .
C9 C10 C11 C6 1.9(4) . . . .
C9 C10 C11 C12 -178.6(3) . . . .
C7 C6 C11 C10 0.6(4) . . . .
C5 C6 C11 C10 -177.8(3) . . . .
C7 C6 C11 C12 -178.9(3) . . . .
C5 C6 C11 C12 2.8(4) . . . .
C14 N3 C12 N4 0.9(3) . . . .
Zn1 N3 C12 N4 -178.3(2) . . . .
C14 N3 C12 C11 175.0(3) . . . .
Zn1 N3 C12 C11 -4.2(5) . . . .
C15 N4 C12 N3 0.0(3) . . . .
C15 N4 C12 C11 -174.5(2) . . . .
C10 C11 C12 N3 -146.4(3) . . . .
C6 C11 C12 N3 33.0(5) . . . .
C10 C11 C12 N4 27.0(4) . . . .
C6 C11 C12 N4 -153.6(3) . . . .
Zn1 O5 C13 O6 -179.2(2) . . . .
Zn1 O5 C13 C14 3.1(3) . . . .
C12 N3 C14 C15 -1.6(3) . . . .
Zn1 N3 C14 C15 177.89(19) . . . .
C12 N3 C14 C13 176.5(2) . . . .
Zn1 N3 C14 C13 -4.0(3) . . . .
O6 C13 C14 C15 0.4(5) . . . .
O5 C13 C14 C15 178.3(3) . . . .
O6 C13 C14 N3 -177.1(3) . . . .
O5 C13 C14 N3 0.7(4) . . . .
N3 C14 C15 N4 1.6(3) . . . .
C13 C14 C15 N4 -176.1(3) . . . .
N3 C14 C15 C16 -171.9(3) . . . .
C13 C14 C15 C16 10.4(6) . . . .
C12 N4 C15 C14 -1.0(3) . . . .
C12 N4 C15 C16 173.4(3) . . . .
C14 C15 C16 O8 167.6(3) . . . .
N4 C15 C16 O8 -5.0(5) . . . .
C14 C15 C16 O7 -10.4(5) . . . .
N4 C15 C16 O7 176.9(3) . . . .
