#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/51/2215135.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_2215135
loop_
_publ_author_name
'Broker, Grant A.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Bis(μ-pyridine-1-carbaldehyde
 azine-κ²N,N':κN'')disilver(I)
 bis(p-toluenesulfonate)
;
_journal_coeditor_code           HB2512
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2420
_journal_page_last               m2421
_journal_paper_doi               10.1107/S1600536807040809
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Ag2 (C12 H10 N4)2] (C7 H7 S O3)2'
_chemical_formula_moiety         'C24 H20 Ag2 N8 2+, 2(C7 H7 S1 O3 -)'
_chemical_formula_sum            'C38 H34 Ag2 N8 O6 S2'
_chemical_formula_weight         978.61
_chemical_name_systematic
;
Bis(μ-pyridine-1-carbaldehyde azine-κ²N,N':\kN'')disilver(I)
bis(p-toluenesulfonate)
;
_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           SHELXL-97
_cell_angle_alpha                78.12(3)
_cell_angle_beta                 76.75(3)
_cell_angle_gamma                70.13(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9619(17)
_cell_length_b                   9.4382(11)
_cell_length_c                   13.468(3)
_cell_measurement_reflns_used    2621
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      2.6
_cell_volume                     917.4(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku/MSC AFC12κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0.017
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10013
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.6
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.020
_refine_ls_R_factor_gt           0.020
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0249P)²+0.8243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.051
_refine_ls_wR_factor_ref         0.052
_reflns_number_gt                3713
_reflns_number_total             3776
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2512.cif
_cod_data_source_block           I
_cod_original_cell_volume        917.4(3)
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      ' P -1'
_cod_database_code               2215135
_cod_database_fobs_code          2215135
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
Ag Ag 0.270539(16) 0.533834(14) 0.880628(10) 0.01623(5) Uani d . 1
S S1 0.11139(5) 0.33155(5) 0.76383(3) 0.01453(9) Uani d . 1
O O1 0.00032(19) 0.46865(17) 0.71172(12) 0.0307(3) Uani d . 1
O O2 0.12104(17) 0.34521(16) 0.86852(10) 0.0209(3) Uani d . 1
O O3 0.06566(18) 0.19598(16) 0.76129(11) 0.0228(3) Uani d . 1
N N1 -0.45024(19) 0.65008(17) 1.01938(11) 0.0142(3) Uani d . 1
N N2 -0.12641(19) 0.81213(17) 0.85496(12) 0.0161(3) Uani d . 1
N N3 0.06292(19) 0.75793(17) 0.82718(11) 0.0143(3) Uani d . 1
N N4 0.4262(2) 0.67661(17) 0.74678(11) 0.0152(3) Uani d . 1
C C1 -0.6304(2) 0.6843(2) 1.05199(14) 0.0161(3) Uani d . 1
H H1 -0.6753 0.6118 1.1009 0.019 Uiso calc R 1
C C2 -0.7532(2) 0.8191(2) 1.01822(14) 0.0186(4) Uani d . 1
H H2 -0.8793 0.8389 1.0440 0.022 Uiso calc R 1
C C3 -0.6897(2) 0.9254(2) 0.94594(14) 0.0187(4) Uani d . 1
H H3 -0.7708 1.0198 0.9218 0.022 Uiso calc R 1
C C4 -0.5054(2) 0.8904(2) 0.91000(14) 0.0167(3) Uani d . 1
H H4 -0.4581 0.9597 0.8593 0.020 Uiso calc R 1
C C5 -0.3897(2) 0.75296(19) 0.94858(13) 0.0134(3) Uani d . 1
C C6 -0.1924(2) 0.7123(2) 0.91352(13) 0.0139(3) Uani d . 1
H H6 -0.1156 0.6136 0.9341 0.017 Uiso calc R 1
C C7 0.1246(2) 0.8529(2) 0.75909(14) 0.0153(3) Uani d . 1
H H7 0.0433 0.9466 0.7340 0.018 Uiso calc R 1
C C8 0.3194(2) 0.8182(2) 0.71959(13) 0.0139(3) Uani d . 1
C C9 0.6040(2) 0.6460(2) 0.71350(14) 0.0166(3) Uani d . 1
H H9 0.6807 0.5462 0.7316 0.020 Uiso calc R 1
C C10 0.6828(2) 0.7538(2) 0.65329(14) 0.0182(4) Uani d . 1
H H10 0.8106 0.7283 0.6322 0.022 Uiso calc R 1
C C11 0.5717(2) 0.8983(2) 0.62486(14) 0.0179(4) Uani d . 1
H H11 0.6218 0.9737 0.5837 0.021 Uiso calc R 1
C C12 0.3859(2) 0.9314(2) 0.65742(14) 0.0166(3) Uani d . 1
H H12 0.3060 1.0291 0.6377 0.020 Uiso calc R 1
C C13 0.3356(2) 0.30503(19) 0.69408(13) 0.0138(3) Uani d . 1
C C14 0.4828(2) 0.2515(2) 0.74534(14) 0.0154(3) Uani d . 1
H H14 0.4638 0.2270 0.8182 0.018 Uiso calc R 1
C C15 0.6573(2) 0.2336(2) 0.69066(15) 0.0183(4) Uani d . 1
H H15 0.7570 0.1982 0.7264 0.022 Uiso calc R 1
C C16 0.6874(2) 0.2671(2) 0.58368(15) 0.0179(4) Uani d . 1
C C17 0.5387(3) 0.3178(2) 0.53321(14) 0.0193(4) Uani d . 1
H H17 0.5576 0.3392 0.4602 0.023 Uiso calc R 1
C C18 0.3635(2) 0.3377(2) 0.58741(14) 0.0167(3) Uani d . 1
H H18 0.2636 0.3733 0.5518 0.020 Uiso calc R 1
C C19 0.8762(3) 0.2497(3) 0.52383(17) 0.0287(5) Uani d . 1
H H19A 0.9352 0.1436 0.5120 0.043 Uiso calc R 1
H H19B 0.9463 0.2783 0.5631 0.043 Uiso calc R 1
H H19C 0.8698 0.3158 0.4575 0.043 Uiso calc R 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'
Ag Ag -0.8971 1.1015 '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'
S S 0.1246 0.1234 '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
N1 Ag N3 2_567 . 161.06(6) y
N1 Ag N4 2_567 . 114.74(6) y
N3 Ag N4 . . 71.65(6) y
N1 Ag O2 2_567 . 88.50(5) ?
N3 Ag O2 . . 100.89(5) ?
N4 Ag O2 . . 129.62(5) ?
O1 S1 O3 . . 113.74(9) ?
O1 S1 O2 . . 113.34(10) ?
O3 S1 O2 . . 111.55(9) ?
O1 S1 C13 . . 105.70(9) ?
O3 S1 C13 . . 106.41(8) ?
O2 S1 C13 . . 105.28(8) ?
S1 O2 Ag . . 115.18(8) ?
C1 N1 C5 . . 117.32(15) ?
C1 N1 Ag . 2_567 117.09(12) ?
C5 N1 Ag . 2_567 122.77(11) ?
C6 N2 N3 . . 112.67(15) ?
C7 N3 N2 . . 111.79(15) ?
C7 N3 Ag . . 116.87(12) ?
N2 N3 Ag . . 131.33(11) ?
C9 N4 C8 . . 117.66(15) ?
C9 N4 Ag . . 128.25(12) ?
C8 N4 Ag . . 112.49(11) ?
N1 C1 C2 . . 123.45(17) ?
N1 C1 H1 . . 118.3 ?
C2 C1 H1 . . 118.3 ?
C1 C2 C3 . . 118.92(17) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 118.26(17) ?
C4 C3 H3 . . 120.9 ?
C2 C3 H3 . . 120.9 ?
C3 C4 C5 . . 119.54(17) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
N1 C5 C4 . . 122.48(16) ?
N1 C5 C6 . . 116.29(15) ?
C4 C5 C6 . . 121.23(16) ?
N2 C6 C5 . . 118.72(16) ?
N2 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
N3 C7 C8 . . 120.49(16) ?
N3 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
N4 C8 C12 . . 123.14(16) ?
N4 C8 C7 . . 117.51(15) ?
C12 C8 C7 . . 119.34(16) ?
N4 C9 C10 . . 123.02(17) ?
N4 C9 H9 . . 118.5 ?
C10 C9 H9 . . 118.5 ?
C11 C10 C9 . . 118.79(16) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C10 C11 C12 . . 118.95(17) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C11 C12 C8 . . 118.39(17) ?
C11 C12 H12 . . 120.8 ?
C8 C12 H12 . . 120.8 ?
C18 C13 C14 . . 119.87(16) ?
C18 C13 S1 . . 119.54(14) ?
C14 C13 S1 . . 120.59(14) ?
C15 C14 C13 . . 120.36(17) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 120.44(17) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C17 . . 118.51(17) ?
C15 C16 C19 . . 120.79(18) ?
C17 C16 C19 . . 120.70(18) ?
C18 C17 C16 . . 121.39(17) ?
C18 C17 H17 . . 119.3 ?
C16 C17 H17 . . 119.3 ?
C17 C18 C13 . . 119.41(17) ?
C17 C18 H18 . . 120.3 ?
C13 C18 H18 . . 120.3 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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
Ag N1 2_567 2.2596(17) y
Ag N3 . 2.2948(17) y
Ag N4 . 2.3900(17) y
Ag O2 . 2.5023(14) ?
S1 O1 . 1.4428(15) ?
S1 O3 . 1.4530(14) ?
S1 O2 . 1.4636(14) ?
S1 C13 . 1.7768(18) ?
N1 C1 . 1.345(2) ?
N1 C5 . 1.346(2) ?
N1 Ag 2_567 2.2596(17) ?
N2 C6 . 1.275(2) ?
N2 N3 . 1.404(2) ?
N3 C7 . 1.280(2) ?
N4 C9 . 1.332(2) ?
N4 C8 . 1.346(2) ?
C1 C2 . 1.379(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.381(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.389(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.470(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.464(2) ?
C7 H7 . 0.9500 ?
C8 C12 . 1.391(2) ?
C9 C10 . 1.396(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.387(3) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C18 . 1.388(3) ?
C13 C14 . 1.389(2) ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.392(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.394(3) ?
C16 C19 . 1.506(3) ?
C17 C18 . 1.387(3) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
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
C9 H9 O1 1_655 0.95 2.36 3.025(2) 126 y
C10 H10 O1 1_655 0.95 2.56 3.109(2) 117 y
C14 H14 O2 1_555 0.95 2.56 2.918(2) 103 y
C7 H7 O3 1_565 0.95 2.53 3.116(2) 120 y
C12 H12 O3 1_565 0.95 2.55 3.189(2) 125 y
C15 H15 O3 1_655 0.95 2.60 3.478(2) 154 y
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_site_symmetry_1
_geom_torsion
O1 S1 O2 Ag . -64.41(10)
O3 S1 O2 Ag . 165.65(7)
C13 S1 O2 Ag . 50.64(10)
N1 Ag O2 S1 2_567 -128.37(9)
N3 Ag O2 S1 . 68.20(9)
N4 Ag O2 S1 . -6.91(11)
C6 N2 N3 C7 . 172.35(16)
C6 N2 N3 Ag . -6.7(2)
N1 Ag N3 C7 2_567 109.39(19)
N4 Ag N3 C7 . -3.67(13)
O2 Ag N3 C7 . -132.02(13)
N1 Ag N3 N2 2_567 -71.6(2)
N4 Ag N3 N2 . 175.35(16)
O2 Ag N3 N2 . 47.01(15)
N1 Ag N4 C9 2_567 12.19(17)
N3 Ag N4 C9 . 172.99(16)
O2 Ag N4 C9 . -97.93(16)
N1 Ag N4 C8 2_567 -152.90(11)
N3 Ag N4 C8 . 7.90(11)
O2 Ag N4 C8 . 96.97(13)
C5 N1 C1 C2 . -1.3(3)
Ag N1 C1 C2 2_567 160.20(14)
N1 C1 C2 C3 . 0.7(3)
C1 C2 C3 C4 . 0.8(3)
C2 C3 C4 C5 . -1.6(3)
C1 N1 C5 C4 . 0.5(3)
Ag N1 C5 C4 2_567 -159.94(13)
C1 N1 C5 C6 . -179.49(15)
Ag N1 C5 C6 2_567 20.1(2)
C3 C4 C5 N1 . 1.0(3)
C3 C4 C5 C6 . -179.05(17)
N3 N2 C6 C5 . -179.77(14)
N1 C5 C6 N2 . -172.63(16)
C4 C5 C6 N2 . 7.4(3)
N2 N3 C7 C8 . 179.92(15)
Ag N3 C7 C8 . -0.9(2)
C9 N4 C8 C12 . 1.2(3)
Ag N4 C8 C12 . 168.05(14)
C9 N4 C8 C7 . -178.06(16)
Ag N4 C8 C7 . -11.25(19)
N3 C7 C8 N4 . 8.7(3)
N3 C7 C8 C12 . -170.59(17)
C8 N4 C9 C10 . 0.6(3)
Ag N4 C9 C10 . -163.79(14)
N4 C9 C10 C11 . -1.4(3)
C9 C10 C11 C12 . 0.3(3)
C10 C11 C12 C8 . 1.5(3)
N4 C8 C12 C11 . -2.3(3)
C7 C8 C12 C11 . 176.99(16)
O1 S1 C13 C18 . -38.59(17)
O3 S1 C13 C18 . 82.66(16)
O2 S1 C13 C18 . -158.82(14)
O1 S1 C13 C14 . 141.67(15)
O3 S1 C13 C14 . -97.07(16)
O2 S1 C13 C14 . 21.44(17)
C18 C13 C14 C15 . 1.4(3)
S1 C13 C14 C15 . -178.83(14)
C13 C14 C15 C16 . -0.9(3)
C14 C15 C16 C17 . -0.4(3)
C14 C15 C16 C19 . 179.30(18)
C15 C16 C17 C18 . 1.2(3)
C19 C16 C17 C18 . -178.54(18)
C16 C17 C18 C13 . -0.6(3)
C14 C13 C18 C17 . -0.7(3)
S1 C13 C18 C17 . 179.58(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072936
