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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500024.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_4500024
loop_
_publ_author_name
'Duong, Adam'
'Valérie Métivaud'
'Maris, Thierry'
'Wuest,James D'
_publ_section_title
;
 Surrogates of 2,2'-Bipyridine Designed to Chelate Ag(I) and Create
 Metallotectons for Engineering Hydrogen-Bonded Crystals
;
_journal_name_full               'Cryst. Growth & Design'
_journal_page_first              2026
_journal_page_last               2034
_journal_paper_doi               10.1021/cg2003194
_journal_volume                  11
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C16 H16 Ag N12, 2(C2 H3 N), Cl O4'
_chemical_formula_sum            'C20 H22 Ag Cl N14 O4'
_chemical_formula_weight         665.84
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 115.300(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5537(8)
_cell_length_b                   7.5440(6)
_cell_length_c                   18.6318(14)
_cell_measurement_reflns_used    9789
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.91
_cell_measurement_theta_min      4.24
_cell_volume                     1341.13(18)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, )'
_computing_data_collection       'APEX2  (Bruker AXS, 1)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, )'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18209
_diffrn_reflns_theta_full        68.09
_diffrn_reflns_theta_max         68.09
_diffrn_reflns_theta_min         4.63
_exptl_absorpt_coefficient_mu    7.440
_exptl_absorpt_correction_T_max  0.6399
_exptl_absorpt_correction_T_min  0.3498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0652
_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)+(0.1170P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                2068
_reflns_number_total             2398
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           adam26
_cod_original_cell_volume        1341.12(18)
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4500024
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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 0.5000 0.58604(6) 0.2500 0.0709(2) Uani 1 2 d S . .
N1 N 0.3574(3) 0.7515(4) 0.1403(2) 0.0552(8) Uani 1 1 d . . .
N2 N 0.4902(3) 0.4448(4) 0.1374(2) 0.0482(7) Uani 1 1 d . . .
N3 N 0.5150(3) 0.1949(3) 0.06665(19) 0.0474(6) Uani 1 1 d . . .
N4 N 0.3507(3) 0.4243(3) -0.0005(2) 0.0486(7) Uani 1 1 d . . .
N5 N 0.6538(4) 0.2271(5) 0.1996(2) 0.0689(9) Uani 1 1 d . . .
H5A H 0.6960 0.1273 0.1983 0.083 Uiso 1 1 calc . . .
H5B H 0.6798 0.2857 0.2445 0.083 Uiso 1 1 calc . . .
N6 N 0.3740(3) 0.1779(4) -0.0662(2) 0.0553(7) Uani 1 1 d . . .
H6A H 0.4140 0.0761 -0.0670 0.066 Uiso 1 1 calc . . .
H6B H 0.3078 0.2207 -0.1101 0.066 Uiso 1 1 calc . . .
C1 C 0.3026(5) 0.9108(5) 0.1423(4) 0.0721(13) Uani 1 1 d . . .
H1 H 0.3256 0.9646 0.1924 0.087 Uiso 1 1 calc R . .
C2 C 0.2140(5) 1.0005(6) 0.0744(4) 0.0768(14) Uani 1 1 d . . .
H2 H 0.1756 1.1122 0.0780 0.092 Uiso 1 1 calc R . .
C3 C 0.1829(6) 0.9237(6) 0.0018(4) 0.0787(16) Uani 1 1 d . . .
H3 H 0.1232 0.9831 -0.0456 0.094 Uiso 1 1 calc R . .
C4 C 0.2380(4) 0.7618(5) -0.0020(3) 0.0574(9) Uani 1 1 d . . .
H4 H 0.2173 0.7070 -0.0517 0.069 Uiso 1 1 calc R . .
C5 C 0.3258(3) 0.6789(4) 0.0692(2) 0.0493(8) Uani 1 1 d . . .
C6 C 0.3925(3) 0.5043(4) 0.0681(2) 0.0450(7) Uani 1 1 d . . .
C7 C 0.5504(3) 0.2894(4) 0.1334(2) 0.0485(8) Uani 1 1 d . . .
C8 C 0.4132(3) 0.2664(4) 0.0011(2) 0.0458(7) Uani 1 1 d . . .
Cl1 Cl 1.0000 -0.0111(2) 0.2500 0.0676(4) Uani 1 2 d S . .
O1 O 0.8816(3) -0.0942(5) 0.23147(19) 0.0869(11) Uani 1 1 d D . .
O2 O 0.9792(4) 0.1148(6) 0.1812(3) 0.0991(12) Uani 1 1 d D . .
N7 N 0.8385(6) 0.3986(7) 0.3553(5) 0.121(2) Uani 1 1 d D . .
C9 C 0.9164(8) 0.5076(10) 0.3784(6) 0.094(2) Uani 0.625(8) 1 d PD A 1
C10 C 1.0099(7) 0.6474(9) 0.4135(7) 0.094(2) Uani 0.625(8) 1 d PD A 1
H10A H 0.9999 0.6887 0.4607 0.141 Uiso 0.625(8) 1 calc PR A 1
H10B H 0.9891 0.7451 0.3755 0.141 Uiso 0.625(8) 1 calc PR A 1
H10C H 1.1061 0.6062 0.4289 0.141 Uiso 0.625(8) 1 calc PR A 1
C9B C 0.9269(11) 0.450(2) 0.3441(10) 0.094(2) Uani 0.375(8) 1 d PD A 2
C10B C 1.0344(11) 0.5150(19) 0.3262(9) 0.094(2) Uani 0.375(8) 1 d PD A 2
H10D H 1.0703 0.4188 0.3047 0.141 Uiso 0.375(8) 1 calc PR A 2
H10E H 1.1105 0.5614 0.3746 0.141 Uiso 0.375(8) 1 calc PR A 2
H10F H 0.9978 0.6101 0.2868 0.141 Uiso 0.375(8) 1 calc PR A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 AG1 N2 . 2_655 125.19(14) y
N2 AG1 N1 . 2_655 143.86(10) y
N2 AG1 N1 2_655 2_655 71.83(11) y
N2 AG1 N1 . . 71.83(11) y
N2 AG1 N1 2_655 . 143.86(10) y
N1 AG1 N1 2_655 . 114.83(16) y
C5 N1 C1 . . 117.8(4) y
C5 N1 AG1 . . 116.5(2) y
C1 N1 AG1 . . 125.7(4) y
C6 N2 C7 . . 115.1(3) y
C6 N2 AG1 . . 115.9(2) y
C7 N2 AG1 . . 127.6(2) y
C7 N3 C8 . . 115.3(3) y
C6 N4 C8 . . 115.2(3) y
C7 N5 H5A . . 120 ?
C7 N5 H5B . . 120 ?
H5A N5 H5B . . 120 ?
C8 N6 H6A . . 120 ?
C8 N6 H6B . . 120 ?
H6A N6 H6B . . 120 ?
N1 C1 C2 . . 122.9(5) y
N1 C1 H1 . . 118.5 ?
C2 C1 H1 . . 118.5 ?
C3 C2 C1 . . 118.4(4) y
C3 C2 H2 . . 120.8 ?
C1 C2 H2 . . 120.8 ?
C4 C3 C2 . . 119.9(4) y
C4 C3 H3 . . 120 ?
C2 C3 H3 . . 120 ?
C3 C4 C5 . . 118.3(5) y
C3 C4 H4 . . 120.9 ?
C5 C4 H4 . . 120.9 ?
N1 C5 C4 . . 122.7(3) y
N1 C5 C6 . . 117.0(3) y
C4 C5 C6 . . 120.3(4) y
N4 C6 N2 . . 125.9(3) y
N4 C6 C5 . . 117.1(3) y
N2 C6 C5 . . 117.0(3) y
N5 C7 N3 . . 117.6(3) y
N5 C7 N2 . . 118.2(4) y
N3 C7 N2 . . 124.2(3) y
N6 C8 N3 . . 117.6(3) y
N6 C8 N4 . . 118.2(3) y
N3 C8 N4 . . 124.3(3) y
O1 CL1 O1 . 2_755 122.6(3) y
O1 CL1 O2 . 2_755 107.28(11) y
O1 CL1 O2 2_755 2_755 107.28(11) y
O1 CL1 O2 . . 107.28(11) y
O1 CL1 O2 2_755 . 107.28(11) y
O2 CL1 O2 2_755 . 103.5(4) y
C9B N7 C9 . . 43.1(1) y
N7 C9 C10 . . 174.3(12) y
N7 C9B C10B . . 177.3(17) y
C9B C10B H10D . . 109.5 ?
C9B C10B H10E . . 109.5 ?
H10D C10B H10E . . 109.5 ?
C9B C10B H10F . . 109.5 ?
H10D C10B H10F . . 109.5 ?
H10E C10B H10F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ag1 N2 . 2.315(3) y
Ag1 N2 2_655 2.315(3) y
Ag1 N1 2_655 2.318(3) y
Ag1 N1 . 2.318(3) y
N1 C5 . 1.337(5) y
N1 C1 . 1.341(5) y
N2 C6 . 1.340(5) y
N2 C7 . 1.350(4) y
N3 C7 . 1.341(5) y
N3 C8 . 1.348(4) y
N4 C6 . 1.308(5) y
N4 C8 . 1.356(4) y
N5 C7 . 1.335(5) y
N5 H5a . 0.88 ?
N5 H5b . 0.88 ?
N6 C8 . 1.320(5) y
N6 H6a . 0.88 ?
N6 H6b . 0.88 ?
C1 C2 . 1.385(8) y
C1 H1 . 0.95 ?
C2 C3 . 1.376(9) y
C2 H2 . 0.95 ?
C3 C4 . 1.368(6) y
C3 H3 . 0.95 ?
C4 C5 . 1.400(5) y
C4 H4 . 0.95 ?
C5 C6 . 1.498(5) y
Cl1 O1 . 1.306(4) y
Cl1 O1 2_755 1.306(4) y
Cl1 O2 2_755 1.535(5) y
Cl1 O2 . 1.535(5) y
N7 C9b . 1.1103(9) y
N7 C9 . 1.1111(9) y
C9 C10 . 1.401(1) y
C10 H10a . 0.98 ?
C10 H10b . 0.98 ?
C10 H10c . 0.98 ?
C9b C10b . 1.4002(9) y
C10b H10d . 0.98 ?
C10b H10e . 0.98 ?
C10b H10f . 0.98 ?
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
N5 H5A O1 0.88 2.44 3.284(4) 159.7 .
N5 H5B N7 0.88 2.2 3.009(8) 152.8 .
N6 H6A N3 0.88 2.18 3.048(4) 170.8 3_655
N6 H6B O1 0.88 2.48 3.171(5) 135.8 3_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144280
