#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009076.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_2009076 loop_ _publ_author_name 'S. Shanmuga Sundara Raj' 'Hoong-Kun Fun' 'Xiao-Feng Chen' 'Xu-Hui Zhu' 'Xiao-Zeng You' _publ_section_title ; Bis[2-(phenylazo)imidazole-N]silver(I) nitrate methanol solvate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1644 _journal_page_last 1646 _journal_paper_doi 10.1107/S0108270199008525 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac '[Ag (C9 H8 N4)2] N O3 , C H3 O H' _chemical_formula_sum 'C19 H20 Ag N9 O4' _chemical_formula_weight 546.31 _chemical_name_systematic ; bis(2-phenyldiazenyl-1H-imidazole-N)silver(I) nitrate methanol solvate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL-97 _cell_angle_alpha 74.0770(10) _cell_angle_beta 75.3590(10) _cell_angle_gamma 72.4620(10) _cell_formula_units_Z 2 _cell_length_a 7.5447(5) _cell_length_b 12.0046(7) _cell_length_c 13.7852(8) _cell_measurement_reflns_used 4099 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.31 _cell_measurement_theta_min 1.56 _cell_volume 1124.96(12) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PLATON (Spek, 1990)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'Siemens SMART CCD area detector' _diffrn_measurement_method '\w 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 0.029 _diffrn_reflns_av_sigmaI/netI 0.062 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7937 _diffrn_reflns_theta_full 28.29 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_min 1.56 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.942 _exptl_absorpt_correction_T_max 0.879 _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 1.477 _refine_diff_density_min -0.561 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 314 _refine_ls_number_reflns 5431 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.094 _refine_ls_R_factor_gt 0.057 _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/[\s^2^(Fo^2^)+(0.0798P)^2^+0.2004P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.160 _reflns_number_gt 3463 _reflns_number_total 5431 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file sk1302.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 2009076 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Ag1 -.23310(6) .02537(3) .24568(3) .07257(19) Uani d . 1 . . Ag O1 -.3683(6) .4256(4) -.1924(3) .0827(11) Uani d . 1 . . O O2 -.6569(6) .4245(4) -.1713(3) .0861(12) Uani d . 1 . . O O3 -.5311(5) .5308(3) -.3085(2) .0733(9) Uani d . 1 . . O O4 -.8951(6) .6247(4) -.3478(3) .0865(12) Uani d . 1 . . O N1 -.4044(5) .1714(3) .1532(2) .0489(8) Uani d . 1 . . N N2 -.5027(5) .2820(3) .0129(2) .0564(9) Uani d . 1 . . N H2A -.5229 .3030 -.0490 .068 Uiso calc R 1 . . H N3 -.3295(5) .0854(3) -.0014(2) .0524(8) Uani d . 1 . . N N4 -.2510(5) -.0100(3) .0493(3) .0544(8) Uani d . 1 . . N N5 -.0434(5) -.1206(3) .3260(3) .0511(8) Uani d . 1 . . N N6 .0579(5) -.2482(3) .4616(3) .0536(9) Uani d . 1 . . N H6A .0724 -.2786 .5241 .064 Uiso calc R 1 . . H N7 -.1635(5) -.0708(3) .4965(3) .0498(8) Uani d . 1 . . N N8 -.2634(5) .0257(3) .4553(3) .0506(8) Uani d . 1 . . N N9 -.5193(6) .4602(3) -.2240(3) .0549(9) Uani d . 1 . . N C1 -.5611(6) .3517(4) .0817(3) .0575(11) Uani d . 1 . . C H1A -.6297 .4312 .0718 .069 Uiso calc R 1 . . H C2 -.4999(7) .2829(4) .1688(3) .0569(10) Uani d . 1 . . C H2B -.5200 .3079 .2297 .068 Uiso calc R 1 . . H C3 -.4079(6) .1742(3) .0569(3) .0455(9) Uani d . 1 . . C C4 -.1646(6) -.1039(4) -.0088(3) .0513(10) Uani d . 1 . . C C5 -.0842(7) -.2118(4) .0479(4) .0610(11) Uani d . 1 . . C H5A -.0902 -.2202 .1177 .073 Uiso calc R 1 . . H C6 .0059(8) -.3084(5) .0026(4) .0726(13) Uani d . 1 . . C H6B .0615 -.3815 .0413 .087 Uiso calc R 1 . . H C7 .0124(7) -.2951(5) -.1001(4) .0685(13) Uani d . 1 . . C H7B .0737 -.3597 -.1312 .082 Uiso calc R 1 . . H C8 -.0697(7) -.1886(5) -.1572(4) .0685(13) Uani d . 1 . . C H8B -.0652 -.1818 -.2266 .082 Uiso calc R 1 . . H C9 -.1607(7) -.0894(4) -.1130(3) .0593(11) Uani d . 1 . . C H9A -.2166 -.0164 -.1517 .071 Uiso calc R 1 . . H C10 .1449(6) -.2986(4) .3806(3) .0580(11) Uani d . 1 . . C H10A .2310 -.3728 .3814 .070 Uiso calc R 1 . . H C11 .0818(6) -.2192(4) .2971(3) .0568(10) Uani d . 1 . . C H11A .1190 -.2309 .2303 .068 Uiso calc R 1 . . H C12 -.0554(6) -.1419(4) .4274(3) .0463(9) Uani d . 1 . . C C13 -.3756(6) .1007(4) .5254(3) .0490(9) Uani d . 1 . . C C14 -.4743(7) .2121(4) .4814(3) .0605(11) Uani d . 1 . . C H14A -.4662 .2339 .4105 .073 Uiso calc R 1 . . H C15 -.5855(7) .2918(4) .5418(4) .0679(13) Uani d . 1 . . C H15A -.6525 .3670 .5119 .082 Uiso calc R 1 . . H C16 -.5961(7) .2591(5) .6461(4) .0669(12) Uani d . 1 . . C H16A -.6691 .3128 .6870 .080 Uiso calc R 1 . . H C17 -.4995(7) .1475(5) .6907(4) .0656(12) Uani d . 1 . . C H17A -.5101 .1259 .7617 .079 Uiso calc R 1 . . H C18 -.3876(6) .0675(4) .6318(3) .0557(11) Uani d . 1 . . C H18A -.3211 -.0074 .6622 .067 Uiso calc R 1 . . H C19 -1.0173(11) .5506(8) -.3092(6) .093(2) Uani d . 1 . . C H1O4 -.774(10) .586(6) -.332(5) .11(2) Uiso d . 1 . . H H19C -.987(16) .521(10) -.375(8) .22(5) Uiso d . 1 . . H H19B -1.137(14) .595(8) -.329(7) .16(3) Uiso d . 1 . . H H19A -1.011(12) .497(8) -.244(6) .15(3) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Ag1 .0733(3) .0593(3) .0757(3) -.00068(18) -.0419(2) .00859(17) O1 .073(2) .090(3) .063(2) .008(2) -.0220(17) -.0054(18) O2 .093(3) .107(3) .062(2) -.047(3) -.016(2) .002(2) O3 .090(3) .066(2) .0510(17) -.0134(19) -.0232(16) .0110(15) O4 .077(3) .094(3) .076(2) -.020(2) -.034(2) .020(2) N1 .054(2) .0404(18) .0492(18) -.0019(15) -.0213(15) -.0047(14) N2 .069(2) .051(2) .0412(18) -.0043(18) -.0194(16) -.0003(15) N3 .058(2) .047(2) .0482(18) -.0105(16) -.0163(16) .0003(15) N4 .058(2) .053(2) .0484(19) -.0117(17) -.0148(16) -.0031(16) N5 .0502(19) .0461(19) .0548(19) -.0048(16) -.0222(15) -.0040(15) N6 .055(2) .048(2) .055(2) -.0087(16) -.0247(17) .0018(16) N7 .0506(19) .0447(19) .056(2) -.0125(16) -.0211(16) -.0029(15) N8 .053(2) .0473(19) .0542(19) -.0153(16) -.0225(16) .0002(15) N9 .071(3) .0442(19) .0453(19) -.0050(18) -.0143(18) -.0106(15) C1 .061(3) .043(2) .059(2) .001(2) -.018(2) -.0051(19) C2 .066(3) .052(3) .050(2) .001(2) -.019(2) -.0157(19) C3 .046(2) .041(2) .045(2) -.0050(17) -.0104(17) -.0077(16) C4 .047(2) .050(2) .058(2) -.0118(19) -.0071(19) -.0158(19) C5 .067(3) .056(3) .058(3) -.009(2) -.019(2) -.009(2) C6 .070(3) .054(3) .085(4) .001(2) -.019(3) -.014(2) C7 .062(3) .062(3) .085(4) -.009(2) -.007(3) -.034(3) C8 .068(3) .084(4) .056(3) -.019(3) -.001(2) -.028(3) C9 .056(3) .054(3) .063(3) -.009(2) -.016(2) -.007(2) C10 .055(2) .043(2) .072(3) -.0043(19) -.025(2) -.002(2) C11 .055(2) .058(3) .056(2) -.004(2) -.020(2) -.013(2) C12 .045(2) .043(2) .050(2) -.0094(17) -.0201(17) -.0010(17) C13 .047(2) .045(2) .058(2) -.0158(18) -.0186(18) -.0052(18) C14 .071(3) .052(3) .058(3) -.011(2) -.026(2) -.001(2) C15 .068(3) .049(3) .082(3) -.006(2) -.024(3) -.007(2) C16 .061(3) .061(3) .082(3) -.011(2) -.013(2) -.026(3) C17 .064(3) .083(4) .055(3) -.024(3) -.011(2) -.016(2) C18 .056(3) .051(2) .058(2) -.015(2) -.018(2) .001(2) C19 .080(4) .105(5) .091(5) -.033(4) -.022(4) .003(4) 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_publ_flag N5 Ag1 N1 174.90(10) y C3 N1 C2 105.6(3) ? C3 N1 Ag1 123.0(3) ? C2 N1 Ag1 130.4(3) ? C3 N2 C1 108.3(3) ? N4 N3 C3 111.9(3) y N3 N4 C4 113.7(3) y C12 N5 C11 104.8(3) ? C12 N5 Ag1 122.5(3) ? C11 N5 Ag1 131.6(3) ? C12 N6 C10 107.8(3) ? N8 N7 C12 113.3(3) y N7 N8 C13 114.2(3) y O2 N9 O1 119.4(4) y O2 N9 O3 120.5(4) y O1 N9 O3 120.1(4) y N2 C1 C2 106.2(4) ? C1 C2 N1 109.4(4) ? N1 C3 N2 110.4(3) ? N1 C3 N3 130.7(3) ? N2 C3 N3 118.9(3) ? C5 C4 C9 120.9(4) ? C5 C4 N4 114.2(4) ? C9 C4 N4 124.9(4) ? C4 C5 C6 120.6(4) ? C7 C6 C5 119.1(5) ? C8 C7 C6 120.9(4) ? C7 C8 C9 120.9(5) ? C4 C9 C8 117.6(4) ? N6 C10 C11 106.3(4) ? N5 C11 C10 110.1(4) ? N5 C12 N6 111.1(4) ? N5 C12 N7 129.4(4) ? N6 C12 N7 119.5(3) ? C14 C13 C18 120.0(4) ? C14 C13 N8 115.7(4) ? C18 C13 N8 124.3(4) ? C13 C14 C15 120.4(4) ? C16 C15 C14 119.4(5) ? C15 C16 C17 120.4(5) ? C18 C17 C16 120.9(4) ? C17 C18 C13 118.8(4) ? 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 N5 . 2.138(3) y Ag1 N1 . 2.147(3) y O1 N9 . 1.236(5) y O2 N9 . 1.226(5) y O3 N9 . 1.245(4) y O4 C19 . 1.382(8) y N1 C3 . 1.325(5) ? N1 C2 . 1.362(5) ? N2 C3 . 1.336(5) ? N2 C1 . 1.341(6) ? N3 N4 . 1.229(5) y N3 C3 . 1.408(5) ? N4 C4 . 1.458(6) ? N5 C12 . 1.335(5) ? N5 C11 . 1.359(6) ? N6 C12 . 1.341(5) ? N6 C10 . 1.343(6) ? N7 N8 . 1.250(5) y N7 C12 . 1.390(5) y N8 C13 . 1.438(6) y C1 C2 . 1.357(6) ? C4 C5 . 1.367(6) ? C4 C9 . 1.392(6) ? C5 C6 . 1.379(7) ? C6 C7 . 1.371(7) ? C7 C8 . 1.363(7) ? C8 C9 . 1.399(7) ? C10 C11 . 1.365(6) ? C13 C14 . 1.376(6) ? C13 C18 . 1.396(6) ? C14 C15 . 1.384(7) ? C15 C16 . 1.371(7) ? C16 C17 . 1.374(7) ? C17 C18 . 1.374(7) ? 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 N2 H2A O2 1_555 0.86 2.148 2.939(5) 153 yes O4 H1O4 O3 1_555 0.94(8) 1.83(8) 2.767(6) 172(7) yes N6 H6A O4 1_646 0.86 1.857 2.702(6) 167 yes 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_publ_flag N5 Ag1 N1 C3 39.3(16) ? N5 Ag1 N1 C2 -127.9(14) ? C3 N3 N4 C4 -178.9(3) y N1 Ag1 N5 C12 155.3(13) ? N1 Ag1 N5 C11 -38.5(16) ? C12 N7 N8 C13 -179.7(3) y C3 N2 C1 C2 -0.4(5) ? N2 C1 C2 N1 0.0(5) ? C3 N1 C2 C1 0.4(5) ? Ag1 N1 C2 C1 169.3(3) ? C2 N1 C3 N2 -0.6(5) ? Ag1 N1 C3 N2 -170.5(3) ? C2 N1 C3 N3 179.0(4) ? Ag1 N1 C3 N3 9.0(6) ? C1 N2 C3 N1 0.6(5) ? C1 N2 C3 N3 -179.0(4) ? N4 N3 C3 N1 2.3(6) ? N4 N3 C3 N2 -178.1(4) ? N3 N4 C4 C5 -177.2(4) ? N3 N4 C4 C9 2.8(6) ? C9 C4 C5 C6 1.2(7) ? N4 C4 C5 C6 -178.8(4) ? C4 C5 C6 C7 -0.6(8) ? C5 C6 C7 C8 -0.5(8) ? C6 C7 C8 C9 0.9(8) ? C5 C4 C9 C8 -0.8(7) ? N4 C4 C9 C8 179.2(4) ? C7 C8 C9 C4 -0.3(7) ? C12 N6 C10 C11 0.5(5) ? C12 N5 C11 C10 -0.3(5) ? Ag1 N5 C11 C10 -168.3(3) ? N6 C10 C11 N5 -0.1(5) ? C11 N5 C12 N6 0.6(5) ? Ag1 N5 C12 N6 170.0(3) ? C11 N5 C12 N7 -179.9(4) ? Ag1 N5 C12 N7 -10.5(6) ? C10 N6 C12 N5 -0.7(5) ? C10 N6 C12 N7 179.7(4) ? N8 N7 C12 N5 0.7(6) ? N8 N7 C12 N6 -179.8(3) ? N7 N8 C13 C14 174.4(4) ? N7 N8 C13 C18 -5.2(5) ? C18 C13 C14 C15 0.2(7) ? N8 C13 C14 C15 -179.5(4) ? C13 C14 C15 C16 0.2(7) ? C14 C15 C16 C17 -1.0(7) ? C15 C16 C17 C18 1.4(7) ? C16 C17 C18 C13 -1.0(7) ? C14 C13 C18 C17 0.2(6) ? N8 C13 C18 C17 179.8(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056869