#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230626.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230626
loop_
_publ_author_name
'Dong, Jian-Yu'
'You, Tian-Pa'
_publ_section_title
;
 [3,3'-Dihydroxy-3,3'-bis(pyridin-3-yl-κN)-1,1'-(pyridine-2,6-diyl)dipropan-1-one](nitrato-κ²O,O')silver(I)
;
_journal_coeditor_code           FF2013
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m905
_journal_paper_doi               10.1107/S1600536811020472
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Ag (N O3) (C21 H15 N3 O4)]'
_chemical_formula_moiety         'C21 H15 Ag N4 O7'
_chemical_formula_sum            'C21 H15 Ag N4 O7'
_chemical_formula_weight         543.24
_chemical_name_systematic
;
[3,3'-Dihydroxy-3,3'-bis(pyridin-3-yl-κN)-1,1'-(pyridine-2,6-
diyl)dipropan-1-one](nitrato-κ²O,O')silver(I)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                101.256(3)
_cell_angle_beta                 101.610(3)
_cell_angle_gamma                96.454(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5972(14)
_cell_length_b                   12.572(3)
_cell_length_c                   12.731(3)
_cell_measurement_reflns_used    2396
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.1
_cell_volume                     1001.7(4)
_computing_cell_refinement       'SMART (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5286
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  0.8238
_exptl_absorpt_correction_T_min  0.7208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.407
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0413
_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)+(0.0450P)²+0.3559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                2396
_reflns_number_total             3478
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ff2013.cif
_cod_data_source_block           I
_cod_database_code               2230626
_cod_database_fobs_code          2230626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag Ag1 1.13449(6) 0.10254(4) 0.22826(3) 0.0692(2) Uani d . 1 1 . .
N N1 0.3450(5) 0.3863(3) 0.2614(3) 0.0450(9) Uani d . 1 1 . .
N N2 0.9937(5) 0.1445(3) 0.0679(3) 0.0488(9) Uani d . 1 1 . .
N N3 1.0707(5) 0.1360(3) 0.3959(3) 0.0521(10) Uani d . 1 1 . .
N N4 1.5330(6) 0.0178(3) 0.2232(3) 0.0557(10) Uani d . 1 1 . .
O O1 0.2448(5) 0.4261(3) -0.0112(2) 0.0634(9) Uani d . 1 1 . .
O O2 0.4881(5) 0.3291(3) -0.1132(2) 0.0656(10) Uani d . 1 1 . .
H H2 0.3933 0.3645 -0.1045 0.098 Uiso calc R 1 1 . .
O O3 0.3401(5) 0.3916(3) 0.5397(3) 0.0602(9) Uani d . 1 1 . .
O O4 0.6402(5) 0.2954(3) 0.6191(2) 0.0620(9) Uani d . 1 1 . .
H H4 0.5402 0.3286 0.6193 0.093 Uiso calc R 1 1 . .
O O5 1.4447(6) -0.0098(3) 0.2916(3) 0.0869(12) Uani d . 1 1 . .
O O6 1.4707(6) 0.0916(4) 0.1789(4) 0.0944(14) Uani d . 1 1 . .
O O7 1.6850(5) -0.0217(3) 0.2017(3) 0.0801(11) Uani d . 1 1 . .
C C1 0.2705(7) 0.4022(4) 0.3526(4) 0.0477(11) Uani d . 1 1 . .
C C2 0.0891(7) 0.4478(4) 0.3574(4) 0.0577(13) Uani d . 1 1 . .
H H2A 0.0374 0.4561 0.4208 0.069 Uiso calc R 1 1 . .
C C3 -0.0116(7) 0.4803(4) 0.2665(4) 0.0644(14) Uani d . 1 1 . .
H H3 -0.1324 0.5116 0.2683 0.077 Uiso calc R 1 1 . .
C C4 0.0641(7) 0.4669(4) 0.1741(4) 0.0562(12) Uani d . 1 1 . .
H H4A -0.0014 0.4903 0.1129 0.067 Uiso calc R 1 1 . .
C C5 0.2431(6) 0.4170(4) 0.1730(3) 0.0445(11) Uani d . 1 1 . .
C C6 0.3270(6) 0.3927(4) 0.0730(4) 0.0472(11) Uani d . 1 1 . .
C C7 0.4910(6) 0.3302(4) 0.0706(3) 0.0473(11) Uani d . 1 1 . .
H H7 0.5504 0.3085 0.1341 0.057 Uiso calc R 1 1 . .
C C8 0.5655(6) 0.3005(4) -0.0214(3) 0.0457(11) Uani d . 1 1 . .
C C9 0.8255(7) 0.1952(4) 0.0628(3) 0.0489(12) Uani d . 1 1 . .
H H9 0.7632 0.2034 0.1226 0.059 Uiso calc R 1 1 . .
C C10 0.7390(6) 0.2361(4) -0.0262(3) 0.0425(10) Uani d . 1 1 . .
C C11 0.8261(7) 0.2181(4) -0.1166(4) 0.0581(13) Uani d . 1 1 . .
H H11 0.7708 0.2424 -0.1792 0.070 Uiso calc R 1 1 . .
C C12 0.9963(8) 0.1633(4) -0.1130(4) 0.0618(14) Uani d . 1 1 . .
H H12 1.0570 0.1503 -0.1733 0.074 Uiso calc R 1 1 . .
C C13 1.0752(7) 0.1284(4) -0.0200(4) 0.0491(11) Uani d . 1 1 . .
H H13 1.1906 0.0920 -0.0183 0.059 Uiso calc R 1 1 . .
C C14 0.3917(7) 0.3682(4) 0.4490(4) 0.0502(11) Uani d . 1 1 . .
C C15 0.5630(7) 0.3115(4) 0.4354(4) 0.0528(12) Uani d . 1 1 . .
H H15 0.5966 0.2973 0.3670 0.063 Uiso calc R 1 1 . .
C C16 0.6790(7) 0.2776(4) 0.5204(4) 0.0489(11) Uani d . 1 1 . .
C C17 0.9098(7) 0.1867(4) 0.4105(4) 0.0514(12) Uani d . 1 1 . .
H H17 0.8256 0.2017 0.3489 0.062 Uiso calc R 1 1 . .
C C18 0.8581(7) 0.2187(4) 0.5100(3) 0.0472(11) Uani d . 1 1 . .
C C19 0.9853(8) 0.1955(5) 0.6011(4) 0.0709(16) Uani d . 1 1 . .
H H19 0.9584 0.2159 0.6706 0.085 Uiso calc R 1 1 . .
C C20 1.1518(8) 0.1418(5) 0.5870(4) 0.0694(15) Uani d . 1 1 . .
H H20 1.2377 0.1252 0.6471 0.083 Uiso calc R 1 1 . .
C C21 1.1907(7) 0.1131(4) 0.4856(4) 0.0576(13) Uani d . 1 1 . .
H H21 1.3034 0.0765 0.4774 0.069 Uiso calc R 1 1 . .
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'
Ag Ag -0.8971 1.1015 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Ag1 N2 . . 134.26(12) ?
N3 Ag1 O6 . . 128.04(13) ?
N2 Ag1 O6 . . 92.00(12) ?
N3 Ag1 O5 . . 91.79(12) ?
N2 Ag1 O5 . . 133.95(12) ?
O6 Ag1 O5 . . 48.39(11) ?
C1 N1 C5 . . 118.7(3) ?
C13 N2 C9 . . 117.6(3) ?
C13 N2 Ag1 . . 124.0(3) ?
C9 N2 Ag1 . . 118.2(3) ?
C17 N3 C21 . . 117.3(4) ?
C17 N3 Ag1 . . 117.9(3) ?
C21 N3 Ag1 . . 124.7(3) ?
O5 N4 O7 . . 121.7(4) ?
O5 N4 O6 . . 118.2(4) ?
O7 N4 O6 . . 120.0(4) ?
C8 O2 H2 . . 109.5 ?
C16 O4 H4 . . 109.5 ?
N4 O5 Ag1 . . 89.7(3) ?
N4 O6 Ag1 . . 101.9(3) ?
N1 C1 C2 1 . 122.0(4) ?
N1 C1 C2 . . 122.0(4) ?
N1 C1 C14 1 . 116.5(4) ?
N1 C1 C14 . . 116.5(4) ?
C2 C1 C14 . . 121.5(4) ?
C3 C2 C1 . . 118.5(4) ?
C3 C2 H2A . . 120.8 ?
C1 C2 H2A . . 120.8 ?
C4 C3 C2 . . 120.3(4) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 118.5(4) ?
C3 C4 H4A . . 120.7 ?
C5 C4 H4A . . 120.7 ?
N1 C5 C4 1 . 121.9(4) ?
N1 C5 C4 . . 121.9(4) ?
N1 C5 C6 1 . 116.3(3) ?
N1 C5 C6 . . 116.3(3) ?
C4 C5 C6 . . 121.7(4) ?
O1 C6 C7 1 . 120.8(4) ?
O1 C6 C7 . . 120.8(4) ?
O1 C6 C5 1 . 119.1(4) ?
O1 C6 C5 . . 119.1(4) ?
C7 C6 C5 . . 120.1(4) ?
C8 C7 C6 . . 122.3(4) ?
C8 C7 H7 . . 118.8 ?
C6 C7 H7 . . 118.8 ?
O2 C8 C7 . . 121.5(4) ?
O2 C8 C10 . . 114.8(4) ?
C7 C8 C10 . . 123.6(4) ?
N2 C9 C10 . . 123.8(4) ?
N2 C9 H9 . . 118.1 ?
C10 C9 H9 . . 118.1 ?
C11 C10 C9 . . 117.4(4) ?
C11 C10 C8 . . 122.0(4) ?
C9 C10 C8 . . 120.6(4) ?
C10 C11 C12 . . 119.0(4) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C13 C12 C11 . . 119.4(4) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
N2 C13 C12 . . 122.6(4) ?
N2 C13 H13 . . 118.7 ?
C12 C13 H13 . . 118.7 ?
O3 C14 C15 1 . 122.6(4) ?
O3 C14 C15 . . 122.6(4) ?
O3 C14 C1 1 . 118.7(4) ?
O3 C14 C1 . . 118.7(4) ?
C15 C14 C1 . . 118.7(4) ?
C16 C15 C14 . . 121.4(4) ?
C16 C15 H15 . . 119.3 ?
C14 C15 H15 . . 119.3 ?
O4 C16 C15 . . 122.3(4) ?
O4 C16 C18 . . 114.5(4) ?
C15 C16 C18 . . 123.2(4) ?
N3 C17 C18 . . 124.7(4) ?
N3 C17 H17 . . 117.6 ?
C18 C17 H17 . . 117.6 ?
C17 C18 C19 . . 116.9(4) ?
C17 C18 C16 . . 121.7(4) ?
C19 C18 C16 . . 121.4(4) ?
C20 C19 C18 . . 119.0(5) ?
C20 C19 H19 . . 120.5 ?
C18 C19 H19 . . 120.5 ?
C21 C20 C19 . . 120.1(4) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
N3 C21 C20 . . 122.0(4) ?
N3 C21 H21 . . 119.0 ?
C20 C21 H21 . . 119.0 ?
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 N3 . 2.228(4) ?
Ag1 N2 . 2.253(3) ?
Ag1 O6 . 2.435(4) ?
Ag1 O5 . 2.695(4) ?
N1 C1 . 1.337(5) ?
N1 C5 . 1.338(5) ?
N2 C13 . 1.326(5) ?
N2 C9 . 1.337(5) ?
N3 C17 . 1.324(5) ?
N3 C21 . 1.352(5) ?
N4 O5 . 1.223(5) ?
N4 O7 . 1.223(5) ?
N4 O6 . 1.242(5) ?
O1 C6 . 1.269(5) ?
O2 C8 . 1.312(5) ?
O2 H2 . 0.8200 ?
O3 C14 . 1.258(5) ?
O4 C16 . 1.313(5) ?
O4 H4 . 0.8200 ?
C1 N1 1 1.337(5) ?
C1 C2 . 1.391(6) ?
C1 C14 . 1.489(6) ?
C2 C3 . 1.373(7) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.356(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.399(6) ?
C4 H4A . 0.9300 ?
C5 N1 1 1.338(5) ?
C5 C6 . 1.481(6) ?
C6 O1 1 1.269(5) ?
C6 C7 . 1.408(6) ?
C7 C8 . 1.362(6) ?
C7 H7 . 0.9300 ?
C8 C10 . 1.479(6) ?
C9 C10 . 1.380(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.379(6) ?
C11 C12 . 1.379(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.368(6) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 O3 1 1.258(5) ?
C14 C15 . 1.424(6) ?
C15 C16 . 1.364(6) ?
C15 H15 . 0.9300 ?
C16 C18 . 1.478(6) ?
C17 C18 . 1.375(6) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.390(6) ?
C19 C20 . 1.376(7) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.354(7) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C20 H20 O7 2_856 0.93 2.53 3.386(6) 153.5 yes
C12 H12 O7 2_855 0.93 2.51 3.143(5) 125.9 yes
C9 H9 O6 1_455 0.93 2.56 3.289(6) 135.6 yes
C4 H4A O1 2_565 0.93 2.33 3.205(5) 156.5 yes
O4 H4 O3 . 0.82 1.85 2.572(4) 146.9 yes
O2 H2 O1 . 0.82 1.80 2.531(4) 147.3 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139081383
