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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/54/7235425.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_7235425
loop_
_publ_author_name
'Bodman, Samantha E.'
'Crowther, Anthony C.'
'Geraghty, Paul B.'
'Fitchett, Christopher M.'
_publ_section_title
;
 Structural control: can [2 × 2] silver grids be formed from
 4,5-disubstituted 3,6-di(2-pyridyl) pyridazines?
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              81
_journal_paper_doi               10.1039/C4CE01851F
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C17 H14 Ag N4, Cl O4'
_chemical_formula_sum            'C17 H14 Ag Cl N4 O4'
_chemical_formula_weight         481.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                87.315(3)
_cell_angle_beta                 86.505(3)
_cell_angle_gamma                68.644(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0993(4)
_cell_length_b                   9.7117(4)
_cell_length_c                   11.2515(5)
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     822.43(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19803
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.144
_diffrn_reflns_theta_min         2.703
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.423
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0745 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.8614.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.279
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0358
_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)+(0.0490P)²+0.3400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3550
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01851f1.cif
_cod_data_source_block           4
_cod_database_code               7235425
_shelxl_version_number           2014-3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Ag1 Ag 0.44626(3) 0.68815(2) 0.54377(2) 0.02359(9) Uani 1 1 d .
N1 N 0.3006(3) 0.6590(3) 0.3891(2) 0.0176(5) Uani 1 1 d .
N9 N 0.3448(3) 0.5197(3) 0.3527(2) 0.0187(5) Uani 1 1 d .
N10 N 0.2970(3) 0.9404(3) 0.4367(2) 0.0205(5) Uani 1 1 d .
N16 N 0.5036(3) 0.2362(3) 0.2751(2) 0.0202(5) Uani 1 1 d .
C2 C 0.2233(4) 0.7734(3) 0.3147(3) 0.0170(6) Uani 1 1 d .
C3 C 0.1935(4) 0.7517(3) 0.1983(3) 0.0175(6) Uani 1 1 d .
C4 C 0.1194(4) 0.8597(3) 0.0970(3) 0.0237(7) Uani 1 1 d .
H4A H 0.1562 0.9440 0.0984 0.028 Uiso 1 1 calc R
H4B H -0.0092 0.8942 0.0993 0.028 Uiso 1 1 calc R
C5 C 0.2005(5) 0.7663(4) -0.0122(3) 0.0288(7) Uani 1 1 d .
H5A H 0.1236 0.7999 -0.0787 0.035 Uiso 1 1 calc R
H5B H 0.3155 0.7712 -0.0358 0.035 Uiso 1 1 calc R
C6 C 0.2187(5) 0.6093(3) 0.0278(3) 0.0244(7) Uani 1 1 d .
H6A H 0.1123 0.5900 0.0135 0.029 Uiso 1 1 calc R
H6B H 0.3199 0.5364 -0.0126 0.029 Uiso 1 1 calc R
C7 C 0.2455(4) 0.6091(3) 0.1591(3) 0.0181(6) Uani 1 1 d .
C8 C 0.3185(4) 0.4931(3) 0.2418(3) 0.0174(6) Uani 1 1 d .
C11 C 0.1809(4) 0.9244(3) 0.3631(3) 0.0189(6) Uani 1 1 d .
C12 C 0.0321(4) 1.0421(3) 0.3278(3) 0.0209(6) Uani 1 1 d .
H12 H -0.0479 1.0267 0.2790 0.025 Uiso 1 1 calc R
C13 C 0.0038(4) 1.1832(3) 0.3662(3) 0.0267(7) Uani 1 1 d .
H13 H -0.0943 1.2637 0.3429 0.032 Uiso 1 1 calc R
C14 C 0.1238(5) 1.2013(4) 0.4393(3) 0.0271(7) Uani 1 1 d .
H14 H 0.1095 1.2946 0.4653 0.033 Uiso 1 1 calc R
C15 C 0.2665(4) 1.0780(3) 0.4735(3) 0.0238(7) Uani 1 1 d .
H15 H 0.3455 1.0909 0.5245 0.029 Uiso 1 1 calc R
C17 C 0.3725(4) 0.3348(3) 0.2114(3) 0.0177(6) Uani 1 1 d .
C18 C 0.2896(4) 0.2899(3) 0.1251(3) 0.0225(6) Uani 1 1 d .
H18 H 0.1984 0.3594 0.0839 0.027 Uiso 1 1 calc R
C19 C 0.3430(4) 0.1416(3) 0.1003(3) 0.0253(7) Uani 1 1 d .
H19 H 0.2898 0.1102 0.0416 0.030 Uiso 1 1 calc R
C20 C 0.4766(4) 0.0410(3) 0.1643(3) 0.0254(7) Uani 1 1 d .
H20 H 0.5150 -0.0596 0.1499 0.031 Uiso 1 1 calc R
C21 C 0.5521(4) 0.0930(3) 0.2500(3) 0.0238(7) Uani 1 1 d .
H21 H 0.6419 0.0245 0.2930 0.029 Uiso 1 1 calc R
Cl20 Cl 0.23154(9) 0.37401(8) 0.74298(7) 0.02288(16) Uani 1 1 d .
O21 O 0.3889(3) 0.3395(3) 0.8108(3) 0.0377(6) Uani 1 1 d .
O22 O 0.1849(4) 0.2441(3) 0.7412(3) 0.0474(8) Uani 1 1 d .
O23 O 0.2667(4) 0.4162(4) 0.6233(3) 0.0499(8) Uani 1 1 d .
O24 O 0.0885(3) 0.4922(3) 0.7976(3) 0.0391(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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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 N9 122.04(8) . 2_666
N1 Ag1 N10 70.51(8) . .
N1 Ag1 N16 160.11(9) . 2_666
N9 Ag1 N10 163.04(9) 2_666 .
N16 Ag1 N9 70.91(8) 2_666 2_666
N16 Ag1 N10 100.61(8) 2_666 .
N9 N1 Ag1 116.05(17) . .
C2 N1 Ag1 120.21(19) . .
C2 N1 N9 120.0(2) . .
N1 N9 Ag1 121.79(18) . 2_666
C8 N9 Ag1 114.55(18) . 2_666
C8 N9 N1 120.9(2) . .
C11 N10 Ag1 107.23(19) . .
C11 N10 C15 117.2(3) . .
C15 N10 Ag1 129.8(2) . .
C17 N16 Ag1 116.84(19) . 2_666
C21 N16 Ag1 122.1(2) . 2_666
C21 N16 C17 117.3(3) . .
N1 C2 C3 121.3(3) . .
N1 C2 C11 116.1(2) . .
C3 C2 C11 122.5(2) . .
C2 C3 C4 131.5(3) . .
C7 C3 C2 118.8(3) . .
C7 C3 C4 109.6(3) . .
C3 C4 H4A 111.3 . .
C3 C4 H4B 111.3 . .
C3 C4 C5 102.3(2) . .
H4A C4 H4B 109.2 . .
C5 C4 H4A 111.3 . .
C5 C4 H4B 111.3 . .
C4 C5 H5A 110.8 . .
C4 C5 H5B 110.8 . .
H5A C5 H5B 108.9 . .
C6 C5 C4 104.6(3) . .
C6 C5 H5A 110.8 . .
C6 C5 H5B 110.8 . .
C5 C6 H6A 111.3 . .
C5 C6 H6B 111.3 . .
H6A C6 H6B 109.2 . .
C7 C6 C5 102.4(2) . .
C7 C6 H6A 111.3 . .
C7 C6 H6B 111.3 . .
C3 C7 C6 110.6(3) . .
C3 C7 C8 117.6(3) . .
C8 C7 C6 131.6(3) . .
N9 C8 C7 121.2(3) . .
N9 C8 C17 116.2(2) . .
C7 C8 C17 122.6(3) . .
N10 C11 C2 116.9(2) . .
N10 C11 C12 122.5(3) . .
C12 C11 C2 120.5(3) . .
C11 C12 H12 120.3 . .
C11 C12 C13 119.3(3) . .
C13 C12 H12 120.3 . .
C12 C13 H13 120.7 . .
C14 C13 C12 118.6(3) . .
C14 C13 H13 120.7 . .
C13 C14 H14 120.6 . .
C13 C14 C15 118.8(3) . .
C15 C14 H14 120.6 . .
N10 C15 C14 123.5(3) . .
N10 C15 H15 118.2 . .
C14 C15 H15 118.2 . .
N16 C17 C8 116.6(3) . .
N16 C17 C18 121.8(3) . .
C18 C17 C8 121.6(3) . .
C17 C18 H18 120.1 . .
C19 C18 C17 119.7(3) . .
C19 C18 H18 120.1 . .
C18 C19 H19 120.6 . .
C20 C19 C18 118.8(3) . .
C20 C19 H19 120.6 . .
C19 C20 H20 120.8 . .
C21 C20 C19 118.5(3) . .
C21 C20 H20 120.8 . .
N16 C21 C20 123.9(3) . .
N16 C21 H21 118.1 . .
C20 C21 H21 118.1 . .
O22 Cl20 O21 108.89(17) . .
O23 Cl20 O21 109.75(17) . .
O23 Cl20 O22 109.1(2) . .
O23 Cl20 O24 109.86(18) . .
O24 Cl20 O21 109.51(16) . .
O24 Cl20 O22 109.74(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N1 2.245(2) .
Ag1 N9 2.414(2) 2_666
Ag1 N10 2.580(2) .
Ag1 N16 2.305(3) 2_666
N1 N9 1.345(3) .
N1 C2 1.340(4) .
N9 Ag1 2.414(2) 2_666
N9 C8 1.330(4) .
N10 C11 1.345(4) .
N10 C15 1.348(4) .
N16 Ag1 2.305(3) 2_666
N16 C17 1.358(4) .
N16 C21 1.340(4) .
C2 C3 1.385(4) .
C2 C11 1.500(4) .
C3 C4 1.508(4) .
C3 C7 1.379(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C4 C5 1.529(5) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C5 C6 1.526(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 C7 1.506(4) .
C7 C8 1.403(4) .
C8 C17 1.488(4) .
C11 C12 1.389(4) .
C12 H12 0.9300 .
C12 C13 1.390(4) .
C13 H13 0.9300 .
C13 C14 1.373(5) .
C14 H14 0.9300 .
C14 C15 1.386(5) .
C15 H15 0.9300 .
C17 C18 1.384(4) .
C18 H18 0.9300 .
C18 C19 1.381(4) .
C19 H19 0.9300 .
C19 C20 1.380(5) .
C20 H20 0.9300 .
C20 C21 1.378(5) .
C21 H21 0.9300 .
Cl20 O21 1.450(3) .
Cl20 O22 1.444(3) .
Cl20 O23 1.431(3) .
Cl20 O24 1.431(2) .
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_4
Ag1 N1 N9 Ag1 4.0(3) . 2_666
Ag1 N1 N9 C8 -156.0(2) . .
Ag1 N1 C2 C3 154.9(2) . .
Ag1 N1 C2 C11 -21.9(3) . .
Ag1 N9 C8 C7 -160.8(2) 2_666 .
Ag1 N9 C8 C17 18.5(3) 2_666 .
Ag1 N10 C11 C2 -29.0(3) . .
Ag1 N10 C11 C12 154.0(2) . .
Ag1 N10 C15 C14 -149.5(3) . .
Ag1 N16 C17 C8 20.4(3) 2_666 .
Ag1 N16 C17 C18 -157.7(2) 2_666 .
Ag1 N16 C21 C20 157.3(3) 2_666 .
N1 N9 C8 C7 0.6(4) . .
N1 N9 C8 C17 179.9(3) . .
N1 C2 C3 C4 -176.3(3) . .
N1 C2 C3 C7 -0.2(4) . .
N1 C2 C11 N10 36.2(4) . .
N1 C2 C11 C12 -146.7(3) . .
N9 N1 C2 C3 -2.6(4) . .
N9 N1 C2 C11 -179.3(3) . .
N9 C8 C17 N16 -26.4(4) . .
N9 C8 C17 C18 151.7(3) . .
N10 C11 C12 C13 2.3(5) . .
N16 C17 C18 C19 -1.4(5) . .
C2 N1 N9 Ag1 162.4(2) . 2_666
C2 N1 N9 C8 2.3(4) . .
C2 C3 C4 C5 155.0(3) . .
C2 C3 C7 C6 -174.3(3) . .
C2 C3 C7 C8 3.0(4) . .
C2 C11 C12 C13 -174.7(3) . .
C3 C2 C11 N10 -140.6(3) . .
C3 C2 C11 C12 36.6(4) . .
C3 C4 C5 C6 31.4(3) . .
C3 C7 C8 N9 -3.2(4) . .
C3 C7 C8 C17 177.5(3) . .
C4 C3 C7 C6 2.7(4) . .
C4 C3 C7 C8 179.9(3) . .
C4 C5 C6 C7 -29.8(3) . .
C5 C6 C7 C3 17.3(4) . .
C5 C6 C7 C8 -159.5(3) . .
C6 C7 C8 N9 173.3(3) . .
C6 C7 C8 C17 -6.0(5) . .
C7 C3 C4 C5 -21.4(3) . .
C7 C8 C17 N16 152.9(3) . .
C7 C8 C17 C18 -29.0(5) . .
C8 C17 C18 C19 -179.4(3) . .
C11 N10 C15 C14 -0.1(5) . .
C11 C2 C3 C4 0.3(5) . .
C11 C2 C3 C7 176.4(3) . .
C11 C12 C13 C14 -0.7(5) . .
C12 C13 C14 C15 -1.1(5) . .
C13 C14 C15 N10 1.5(5) . .
C15 N10 C11 C2 175.2(3) . .
C15 N10 C11 C12 -1.8(5) . .
C17 N16 C21 C20 -0.2(5) . .
C17 C18 C19 C20 1.1(5) . .
C18 C19 C20 C21 -0.3(5) . .
C19 C20 C21 N16 -0.1(5) . .
C21 N16 C17 C8 179.0(3) . .
C21 N16 C17 C18 1.0(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339268
