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#$Date: 2023-03-09 11:52:28 +0200 (Thu, 09 Mar 2023) $
#$Revision: 281768 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106895.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_8106895
loop_
_publ_author_name
'Sheng, Liang-Quan'
_publ_section_title
;
 Crystal structure of (4-(1H-imidazol-5-yl)benzoic acid-\kN)
 (4-(1H-imidazol-5-yl)benzoato-\kN)silver(I), C20H15N4O4Ag
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              423
_journal_page_last               425
_journal_paper_doi               10.1515/ncrs-2015-0087
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C20 H15 Ag N4 O4'
_chemical_formula_sum            'C20 H15 Ag N4 O4'
_chemical_formula_weight         483.23
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 109.0630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6344(8)
_cell_length_b                   9.7274(6)
_cell_length_c                   15.7567(10)
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.69
_cell_volume                     1830.3(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11772
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    1.138
_exptl_absorpt_correction_T_max  0.8755
_exptl_absorpt_correction_T_min  0.8214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0330P)²+0.4479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0674
_reflns_number_gt                3467
_reflns_number_total             4196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0087_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106895
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.206902(13) 0.376028(19) 0.011256(11) 0.04318(7) Uani 1 1 d . . .
C1 C 0.54847(16) 0.3946(2) -0.15349(12) 0.0310(4) Uani 1 1 d . . .
C2 C 0.64035(17) 0.3131(3) -0.14873(13) 0.0397(5) Uani 1 1 d . . .
H2 H 0.6661 0.2494 -0.1025 0.048 Uiso 1 1 calc R . .
C3 C 0.69415(17) 0.3255(3) -0.21226(13) 0.0406(5) Uani 1 1 d . . .
H3 H 0.7557 0.2702 -0.2081 0.049 Uiso 1 1 calc R . .
C4 C 0.65748(16) 0.4191(2) -0.28155(12) 0.0332(4) Uani 1 1 d . . .
C5 C 0.56644(19) 0.5023(2) -0.28601(14) 0.0435(5) Uani 1 1 d . . .
H5 H 0.5408 0.5659 -0.3323 0.052 Uiso 1 1 calc R . .
C6 C 0.51370(18) 0.4908(2) -0.22180(14) 0.0417(5) Uani 1 1 d . . .
H6 H 0.4540 0.5486 -0.2246 0.050 Uiso 1 1 calc R . .
C7 C 0.48318(16) 0.3748(2) -0.09243(12) 0.0299(4) Uani 1 1 d . . .
C8 C 0.38399(16) 0.4300(2) -0.09258(12) 0.0326(4) Uani 1 1 d . . .
H8 H 0.3447 0.4982 -0.1315 0.039 Uiso 1 1 calc R . .
C9 C 0.42881(16) 0.2797(2) 0.01268(12) 0.0361(4) Uani 1 1 d . . .
H9 H 0.4276 0.2232 0.0600 0.043 Uiso 1 1 calc R . .
C10 C 0.71123(18) 0.4214(2) -0.35331(13) 0.0385(5) Uani 1 1 d . . .
C11 C -0.09391(15) 0.4297(2) 0.20830(11) 0.0299(4) Uani 1 1 d . . .
C12 C -0.07687(17) 0.5586(2) 0.24736(13) 0.0377(5) Uani 1 1 d . . .
H12 H -0.0343 0.6230 0.2292 0.045 Uiso 1 1 calc R . .
C13 C -0.12278(17) 0.5926(2) 0.31357(13) 0.0364(4) Uani 1 1 d . . .
H13 H -0.1109 0.6798 0.3392 0.044 Uiso 1 1 calc R . .
C14 C -0.18641(15) 0.4973(2) 0.34187(11) 0.0302(4) Uani 1 1 d . . .
C15 C -0.20430(17) 0.3688(2) 0.30235(12) 0.0324(4) Uani 1 1 d . . .
H15 H -0.2473 0.3047 0.3203 0.039 Uiso 1 1 calc R . .
C16 C -0.15867(17) 0.3346(2) 0.23592(12) 0.0327(4) Uani 1 1 d . . .
H16 H -0.1714 0.2478 0.2098 0.039 Uiso 1 1 calc R . .
C17 C -0.04315(16) 0.3923(2) 0.13955(12) 0.0309(4) Uani 1 1 d . . .
C18 C 0.05333(17) 0.4354(2) 0.12756(13) 0.0365(4) Uani 1 1 d . . .
H18 H 0.1016 0.5015 0.1621 0.044 Uiso 1 1 calc R . .
C19 C -0.01770(17) 0.2826(2) 0.02628(13) 0.0388(5) Uani 1 1 d . . .
H19 H -0.0291 0.2232 -0.0221 0.047 Uiso 1 1 calc R . .
C20 C -0.23478(15) 0.5320(2) 0.41508(11) 0.0321(4) Uani 1 1 d . . .
N1 N 0.35068(14) 0.36951(18) -0.02629(11) 0.0341(4) Uani 1 1 d . . .
N2 N 0.51089(13) 0.27930(18) -0.02421(10) 0.0334(4) Uani 1 1 d . . .
H2A H 0.5699 0.2287 -0.0081 0.040 Uiso 1 1 calc R . .
N3 N 0.06856(15) 0.36582(19) 0.05624(12) 0.0384(4) Uani 1 1 d . . .
N4 N -0.08716(14) 0.29445(18) 0.07455(10) 0.0348(4) Uani 1 1 d . . .
H4 H -0.1481 0.2491 0.0664 0.042 Uiso 1 1 calc R . .
O1 O 0.79468(14) 0.3548(2) -0.34793(11) 0.0574(5) Uani 1 1 d . . .
O2 O 0.65705(14) 0.49774(18) -0.42268(10) 0.0499(4) Uani 1 1 d . . .
H2B H 0.6800 0.4811 -0.4646 0.075 Uiso 1 1 calc R . .
O3 O -0.21477(12) 0.65025(16) 0.45001(9) 0.0395(3) Uani 1 1 d . . .
O4 O -0.29419(13) 0.44397(17) 0.43549(9) 0.0462(4) 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'
Ag Ag -0.8971 1.1015 '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
N1 Ag1 N3 174.54(7) . .
C6 C1 C2 118.39(17) . .
C6 C1 C7 119.58(18) . .
C2 C1 C7 121.88(18) . .
C3 C2 C1 120.64(19) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C4 C3 C2 120.8(2) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 118.86(17) . .
C3 C4 C10 119.31(19) . .
C5 C4 C10 121.68(18) . .
C6 C5 C4 120.22(19) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C1 C6 C5 121.06(19) . .
C1 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
C8 C7 N2 105.45(16) . .
C8 C7 C1 131.26(18) . .
N2 C7 C1 123.05(17) . .
C7 C8 N1 109.79(17) . .
C7 C8 H8 125.1 . .
N1 C8 H8 125.1 . .
N1 C9 N2 111.62(17) . .
N1 C9 H9 124.2 . .
N2 C9 H9 124.2 . .
O1 C10 O2 124.27(18) . .
O1 C10 C4 122.4(2) . .
O2 C10 C4 113.28(18) . .
C12 C11 C16 118.97(16) . .
C12 C11 C17 120.60(17) . .
C16 C11 C17 120.42(18) . .
C11 C12 C13 120.53(19) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C12 C13 C14 120.53(19) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C15 C14 C13 118.99(16) . .
C15 C14 C20 119.98(17) . .
C13 C14 C20 121.03(18) . .
C14 C15 C16 120.62(18) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C15 C16 C11 120.36(19) . .
C15 C16 H16 119.8 . .
C11 C16 H16 119.8 . .
C18 C17 N4 105.81(16) . .
C18 C17 C11 130.69(19) . .
N4 C17 C11 123.42(17) . .
C17 C18 N3 109.43(19) . .
C17 C18 H18 125.3 . .
N3 C18 H18 125.3 . .
N3 C19 N4 111.27(18) . .
N3 C19 H19 124.4 . .
N4 C19 H19 124.4 . .
O4 C20 O3 124.31(17) . .
O4 C20 C14 118.08(18) . .
O3 C20 C14 117.59(17) . .
C9 N1 C8 105.65(16) . .
C9 N1 Ag1 118.64(13) . .
C8 N1 Ag1 135.32(14) . .
C9 N2 C7 107.48(16) . .
C9 N2 H2A 126.3 . .
C7 N2 H2A 126.3 . .
C19 N3 C18 105.96(16) . .
C19 N3 Ag1 126.42(14) . .
C18 N3 Ag1 127.42(14) . .
C19 N4 C17 107.54(17) . .
C19 N4 H4 126.2 . .
C17 N4 H4 126.2 . .
C10 O2 H2B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N1 2.0870(16) .
Ag1 N3 2.0921(16) .
C1 C6 1.385(3) .
C1 C2 1.388(3) .
C1 C7 1.470(2) .
C2 C3 1.387(3) .
C2 H2 0.9300 .
C3 C4 1.380(3) .
C3 H3 0.9300 .
C4 C5 1.390(3) .
C4 C10 1.497(2) .
C5 C6 1.386(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.363(3) .
C7 N2 1.377(2) .
C8 N1 1.379(2) .
C8 H8 0.9300 .
C9 N1 1.311(3) .
C9 N2 1.344(2) .
C9 H9 0.9300 .
C10 O1 1.216(3) .
C10 O2 1.314(3) .
C11 C12 1.383(3) .
C11 C16 1.395(3) .
C11 C17 1.473(2) .
C12 C13 1.389(3) .
C12 H12 0.9300 .
C13 C14 1.393(3) .
C13 H13 0.9300 .
C14 C15 1.381(3) .
C14 C20 1.510(2) .
C15 C16 1.391(2) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C18 1.359(3) .
C17 N4 1.376(3) .
C18 N3 1.378(3) .
C18 H18 0.9300 .
C19 N3 1.315(3) .
C19 N4 1.341(2) .
C19 H19 0.9300 .
C20 O4 1.248(2) .
C20 O3 1.264(2) .
N2 H2A 0.8600 .
N4 H4 0.8600 .
O2 H2B 0.8200 .
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
C6 C1 C2 C3 -1.6(3) . . . .
C7 C1 C2 C3 174.0(2) . . . .
C1 C2 C3 C4 -0.1(4) . . . .
C2 C3 C4 C5 0.9(3) . . . .
C2 C3 C4 C10 -174.8(2) . . . .
C3 C4 C5 C6 -0.1(3) . . . .
C10 C4 C5 C6 175.5(2) . . . .
C2 C1 C6 C5 2.4(3) . . . .
C7 C1 C6 C5 -173.3(2) . . . .
C4 C5 C6 C1 -1.6(4) . . . .
C6 C1 C7 C8 5.0(3) . . . .
C2 C1 C7 C8 -170.6(2) . . . .
C6 C1 C7 N2 178.56(19) . . . .
C2 C1 C7 N2 3.0(3) . . . .
N2 C7 C8 N1 -0.3(2) . . . .
C1 C7 C8 N1 174.07(19) . . . .
C3 C4 C10 O1 -8.6(3) . . . .
C5 C4 C10 O1 175.8(2) . . . .
C3 C4 C10 O2 169.1(2) . . . .
C5 C4 C10 O2 -6.4(3) . . . .
C16 C11 C12 C13 0.5(3) . . . .
C17 C11 C12 C13 -178.60(18) . . . .
C11 C12 C13 C14 0.2(3) . . . .
C12 C13 C14 C15 -0.8(3) . . . .
C12 C13 C14 C20 178.74(18) . . . .
C13 C14 C15 C16 0.6(3) . . . .
C20 C14 C15 C16 -178.90(17) . . . .
C14 C15 C16 C11 0.1(3) . . . .
C12 C11 C16 C15 -0.6(3) . . . .
C17 C11 C16 C15 178.45(18) . . . .
C12 C11 C17 C18 29.9(3) . . . .
C16 C11 C17 C18 -149.1(2) . . . .
C12 C11 C17 N4 -153.90(19) . . . .
C16 C11 C17 N4 27.0(3) . . . .
N4 C17 C18 N3 0.2(2) . . . .
C11 C17 C18 N3 176.90(19) . . . .
C15 C14 C20 O4 -2.8(3) . . . .
C13 C14 C20 O4 177.66(18) . . . .
C15 C14 C20 O3 179.04(17) . . . .
C13 C14 C20 O3 -0.5(3) . . . .
N2 C9 N1 C8 0.4(2) . . . .
N2 C9 N1 Ag1 174.29(13) . . . .
C7 C8 N1 C9 0.0(2) . . . .
C7 C8 N1 Ag1 -172.40(14) . . . .
N1 C9 N2 C7 -0.6(2) . . . .
C8 C7 N2 C9 0.6(2) . . . .
C1 C7 N2 C9 -174.44(18) . . . .
N4 C19 N3 C18 -0.3(2) . . . .
N4 C19 N3 Ag1 174.80(13) . . . .
C17 C18 N3 C19 0.0(2) . . . .
C17 C18 N3 Ag1 -174.98(13) . . . .
N3 C19 N4 C17 0.4(2) . . . .
C18 C17 N4 C19 -0.4(2) . . . .
C11 C17 N4 C19 -177.35(18) . . . .
