# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' #TrackingRef '- 1.cif' _journal_coden_Cambridge 0440 _audit_creation_method SHELXL-97 # 1. Submission Details _publ_contact_author_name 'Ulli Englert' _publ_contact_author_address ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; _publ_contact_author_email ullrich.englert@ac.rwth-aachen.de _publ_contact_author_fax 0049-241-8092288 _publ_contact_author_phone 0049-241-8094666 _publ_requested_category ? _publ_requested_coeditor_name ? # 2. Processing Summary (IUCr Office Use Only) # 3. Titl and Author List _publ_section_title ; From crystal to crystal: A new polymorph of (4-carboxylatopyridine) silver(I) by topotactic dehydration of its monohydrate ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address #<--'Last name, first name' #<--'Last name, first name' #<--'Last name, first name' I.Kalf ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; P.Mathieu ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; U.Englert ; Institut fuer Anorganische Chemie RWTH Aachen Landoltweg 1 52074 Aachen Germany ; # 4. Text _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Bruker (1999). SAINT+. Version 6.02. Program for Reduction of Data Collected on Bruker CCD Area Detector Diffractometer, Bruker AXS Inc., Madison, Wisconson, USA. Bruker (2001). SMART. Version 5.624. Program for Bruker CCD X-ray Diffractometer Control. Bruker AXS Inc., Madison, Wisconson, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A. L. (2003). J. Appl. Cryst. 36, 7. ; _publ_section_figure_captions ; ? ; _publ_section_table_legends ; ? ; _publ_section_acknowledgements ; ? ; data_1 _database_code_depnum_ccdc_archive 'CCDC 766378' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'compound 1' _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Ag N O2, H2 O' _chemical_formula_sum 'C6 H6 Ag N O3' _chemical_formula_weight 247.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.6519(5) _cell_length_b 12.1512(18) _cell_length_c 15.070(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.982(4) _cell_angle_gamma 90.00 _cell_volume 668.63(16) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1754 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 24.94 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 2.961 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.410 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_process_details 'PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6029 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.0810 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1447 _reflns_number_gt 941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; The unrestrained anisotropic refinement for the carboxylato oxygen atoms converged for rather prolate adps (ratio max/min 8.3 for O1, 9.3 for O2). Isotropicity restraints (command ISOR in SHELX) for these two atoms, 2 x 6 = 12 restraints in total, gave less prolate adps (ratio max/min 6.1 for O1, 7.3 for O2) and only slightly inferior agreement factors (difference +0.008 in wR2). The su in the SHELX command was chosen as 0.02. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1447 _refine_ls_number_parameters 100 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1366 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.6044(3) 0.57393(8) 0.07548(6) 0.0600(4) Uani 1 1 d . . . O1 O 1.116(2) 0.4462(9) 0.1015(8) 0.093(4) Uani 1 1 d U . . O2 O 1.169(2) 0.2889(9) 0.0226(6) 0.073(3) Uani 1 1 d U . . N1 N 0.617(2) 0.1693(8) 0.3069(5) 0.035(2) Uani 1 1 d . . . C1 C 1.069(3) 0.3409(13) 0.0886(10) 0.064(4) Uani 1 1 d . . . C2 C 0.905(2) 0.2824(8) 0.1646(7) 0.033(2) Uani 1 1 d . . . C3 C 0.861(3) 0.3317(9) 0.2468(8) 0.047(3) Uani 1 1 d . . . H3 H 0.9298 0.4064 0.2555 0.056 Uiso 1 1 calc R . . C4 C 0.720(3) 0.2724(10) 0.3148(7) 0.044(3) Uani 1 1 d . . . H4 H 0.6950 0.3073 0.3708 0.053 Uiso 1 1 calc R . . C5 C 0.660(2) 0.1205(8) 0.2281(6) 0.028(2) Uani 1 1 d . . . H5 H 0.5898 0.0456 0.2218 0.033 Uiso 1 1 calc R . . C6 C 0.801(2) 0.1735(8) 0.1564(6) 0.031(2) Uani 1 1 d . . . H6 H 0.8269 0.1360 0.1016 0.037 Uiso 1 1 calc R . . O3 O 0.245(4) 0.4351(9) 0.4685(7) 0.125(5) Uani 1 1 d . . . H3A H 0.1045 0.4762 0.4984 0.187 Uiso 0.50 1 d PR . . H3B H 0.4344 0.4638 0.4462 0.187 Uiso 1 1 d R . . H3C H 0.2532 0.3682 0.4849 0.187 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0838(8) 0.0606(6) 0.0370(5) -0.0220(4) 0.0390(5) -0.0342(5) O1 0.042(5) 0.088(7) 0.150(10) 0.067(7) 0.006(6) -0.010(5) O2 0.027(4) 0.134(8) 0.058(5) 0.055(6) 0.007(4) 0.001(5) N1 0.025(4) 0.061(6) 0.019(4) 0.001(4) 0.005(3) 0.009(4) C1 0.019(6) 0.086(11) 0.087(11) 0.053(9) 0.005(6) -0.002(6) C2 0.012(5) 0.042(6) 0.046(6) 0.013(5) -0.002(4) -0.001(4) C3 0.036(6) 0.039(6) 0.066(8) -0.015(6) -0.007(6) 0.000(5) C4 0.035(6) 0.058(8) 0.040(6) -0.025(5) 0.001(5) 0.009(5) C5 0.022(5) 0.037(5) 0.025(5) 0.006(4) 0.000(4) 0.004(4) C6 0.029(5) 0.046(6) 0.018(4) -0.004(4) 0.003(4) -0.001(5) O3 0.190(14) 0.113(10) 0.072(7) -0.028(7) 0.046(8) -0.025(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.277(8) 2_655 ? Ag1 O2 2.385(8) 3_765 ? Ag1 O1 2.403(9) 1_455 ? Ag1 O1 2.454(9) . ? Ag1 Ag1 2.9879(17) 3_665 ? O1 C1 1.305(18) . ? O1 Ag1 2.402(9) 1_655 ? O2 C1 1.239(17) . ? O2 Ag1 2.385(8) 3_765 ? N1 C4 1.312(13) . ? N1 C5 1.339(11) . ? N1 Ag1 2.277(8) 2_645 ? C1 C2 1.482(14) . ? C2 C6 1.381(14) . ? C2 C3 1.388(14) . ? C3 C4 1.362(15) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C6 1.366(12) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O3 H3A 0.8500 . ? O3 H3B 0.8500 . ? O3 H3C 0.8499 . ? 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 _geom_angle_publ_flag N1 Ag1 O2 105.0(4) 2_655 3_765 ? N1 Ag1 O1 85.8(4) 2_655 1_455 ? O2 Ag1 O1 145.0(3) 3_765 1_455 ? N1 Ag1 O1 118.5(4) 2_655 . ? O2 Ag1 O1 105.7(3) 3_765 . ? O1 Ag1 O1 97.5(3) 1_455 . ? N1 Ag1 Ag1 144.0(2) 2_655 3_665 ? O2 Ag1 Ag1 92.0(3) 3_765 3_665 ? O1 Ag1 Ag1 63.6(3) 1_455 3_665 ? O1 Ag1 Ag1 85.7(3) . 3_665 ? C1 O1 Ag1 134.9(8) . 1_655 ? C1 O1 Ag1 119.9(8) . . ? Ag1 O1 Ag1 97.5(3) 1_655 . ? C1 O2 Ag1 104.6(9) . 3_765 ? C4 N1 C5 117.7(9) . . ? C4 N1 Ag1 121.3(7) . 2_645 ? C5 N1 Ag1 120.9(7) . 2_645 ? O2 C1 O1 125.4(12) . . ? O2 C1 C2 120.3(13) . . ? O1 C1 C2 114.2(14) . . ? C6 C2 C3 117.2(9) . . ? C6 C2 C1 120.3(11) . . ? C3 C2 C1 122.4(11) . . ? C4 C3 C2 119.6(10) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? N1 C4 C3 123.3(9) . . ? N1 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? N1 C5 C6 123.0(9) . . ? N1 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? C5 C6 C2 119.2(9) . . ? C5 C6 H6 120.4 . . ? C2 C6 H6 120.4 . . ? H3A O3 H3B 118.1 . . ? H3A O3 H3C 115.4 . . ? H3B O3 H3C 118.7 . . ? _diffrn_measured_fraction_theta_max .989 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full .989 _refine_diff_density_max 1.797 _refine_diff_density_min -2.468 _refine_diff_density_rms .208 # Attachment '- 2alpha.cif' data_2alpha _database_code_depnum_ccdc_archive 'CCDC 766379' #TrackingRef '- 2alpha.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'compound 2alpha' _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Ag N O2' _chemical_formula_sum 'C6 H4 Ag N O2' _chemical_formula_weight 229.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.6484(7) _cell_length_b 10.844(2) _cell_length_c 14.425(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.790(3) _cell_angle_gamma 90.00 _cell_volume 569.45(19) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1934 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.67 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 3.453 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.3614 _exptl_absorpt_correction_T_max 0.9341 _exptl_absorpt_process_details 'PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6745 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0684 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1254 _reflns_number_gt 979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1254 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.66665(14) -0.01685(5) 0.39972(4) 0.01780(18) Uani 1 1 d . . . O1 O 1.1232(13) 0.1146(4) 0.4658(3) 0.0165(11) Uani 1 1 d . . . O2 O 1.2107(13) 0.2934(4) 0.5384(3) 0.0186(11) Uani 1 1 d . . . N1 N 0.6288(15) 0.4159(5) 0.2275(4) 0.0157(13) Uani 1 1 d . . . C1 C 1.1010(17) 0.2320(6) 0.4717(5) 0.0132(14) Uani 1 1 d . . . C2 C 0.9294(18) 0.2965(6) 0.3853(5) 0.0143(14) Uani 1 1 d . . . C3 C 0.7856(17) 0.4140(6) 0.3906(5) 0.0144(15) Uani 1 1 d . . . H3 H 0.7886 0.4559 0.4485 0.017 Uiso 1 1 calc R . . C4 C 0.6391(17) 0.4690(6) 0.3114(5) 0.0166(15) Uani 1 1 d . . . H4 H 0.5389 0.5495 0.3161 0.020 Uiso 1 1 calc R . . C5 C 0.7686(18) 0.3018(6) 0.2221(5) 0.0153(15) Uani 1 1 d . . . H5 H 0.7627 0.2619 0.1634 0.018 Uiso 1 1 calc R . . C6 C 0.9211(18) 0.2408(6) 0.2994(5) 0.0164(15) Uani 1 1 d . . . H6 H 1.0201 0.1604 0.2933 0.020 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0144(3) 0.0199(3) 0.0182(3) -0.0019(3) -0.00560(18) 0.0006(2) O1 0.012(2) 0.016(3) 0.021(3) 0.001(2) -0.001(2) -0.0014(19) O2 0.016(3) 0.024(3) 0.015(3) -0.002(2) -0.004(2) 0.001(2) N1 0.006(3) 0.023(3) 0.018(3) 0.001(2) -0.002(2) -0.006(2) C1 0.003(3) 0.024(4) 0.013(4) 0.001(3) 0.002(3) -0.003(3) C2 0.005(3) 0.021(4) 0.016(4) 0.001(3) 0.000(3) -0.004(3) C3 0.006(3) 0.021(4) 0.015(4) -0.003(3) -0.002(3) -0.002(3) C4 0.008(3) 0.018(4) 0.023(4) 0.000(3) -0.002(3) -0.004(3) C5 0.010(3) 0.019(4) 0.017(4) -0.001(3) 0.000(3) -0.002(3) C6 0.009(3) 0.018(4) 0.022(4) 0.002(3) -0.003(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.191(6) 2_645 ? Ag1 O1 2.297(5) 3_756 ? Ag1 O1 2.347(5) . ? Ag1 Ag1 3.2324(12) 3_656 ? O1 C1 1.278(8) . ? O1 Ag1 2.297(5) 3_756 ? O2 C1 1.216(8) . ? N1 C4 1.338(9) . ? N1 C5 1.342(9) . ? N1 Ag1 2.191(6) 2_655 ? C1 C2 1.528(9) . ? C2 C6 1.376(10) . ? C2 C3 1.382(9) . ? C3 C4 1.366(9) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C6 1.382(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? 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 _geom_angle_publ_flag N1 Ag1 O1 132.22(19) 2_645 3_756 ? N1 Ag1 O1 147.1(2) 2_645 . ? O1 Ag1 O1 75.45(18) 3_756 . ? N1 Ag1 Ag1 126.45(15) 2_645 3_656 ? O1 Ag1 Ag1 54.61(12) 3_756 3_656 ? O1 Ag1 Ag1 82.32(12) . 3_656 ? C1 O1 Ag1 115.0(4) . 3_756 ? C1 O1 Ag1 125.8(4) . . ? Ag1 O1 Ag1 104.55(18) 3_756 . ? C4 N1 C5 117.5(6) . . ? C4 N1 Ag1 126.7(5) . 2_655 ? C5 N1 Ag1 115.2(4) . 2_655 ? O2 C1 O1 125.4(6) . . ? O2 C1 C2 119.4(6) . . ? O1 C1 C2 115.2(6) . . ? C6 C2 C3 117.9(6) . . ? C6 C2 C1 121.2(6) . . ? C3 C2 C1 120.9(6) . . ? C4 C3 C2 119.0(6) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? N1 C4 C3 123.6(7) . . ? N1 C4 H4 118.2 . . ? C3 C4 H4 118.2 . . ? N1 C5 C6 121.9(6) . . ? N1 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C2 C6 C5 120.0(6) . . ? C2 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ag1 O1 C1 72.3(7) 2_645 . . . ? O1 Ag1 O1 C1 -136.5(6) 3_756 . . . ? Ag1 Ag1 O1 C1 -81.2(5) 3_656 . . . ? N1 Ag1 O1 Ag1 -151.2(3) 2_645 . . 3_756 ? O1 Ag1 O1 Ag1 -0.002(1) 3_756 . . 3_756 ? Ag1 Ag1 O1 Ag1 55.33(15) 3_656 . . 3_756 ? Ag1 O1 C1 O2 6.9(9) 3_756 . . . ? Ag1 O1 C1 O2 139.6(6) . . . . ? Ag1 O1 C1 C2 -174.8(4) 3_756 . . . ? Ag1 O1 C1 C2 -42.1(8) . . . . ? O2 C1 C2 C6 156.7(7) . . . . ? O1 C1 C2 C6 -21.8(9) . . . . ? O2 C1 C2 C3 -21.7(10) . . . . ? O1 C1 C2 C3 159.8(6) . . . . ? C6 C2 C3 C4 0.7(10) . . . . ? C1 C2 C3 C4 179.1(6) . . . . ? C5 N1 C4 C3 0.5(9) . . . . ? Ag1 N1 C4 C3 170.5(5) 2_655 . . . ? C2 C3 C4 N1 -0.6(10) . . . . ? C4 N1 C5 C6 -0.5(9) . . . . ? Ag1 N1 C5 C6 -171.7(5) 2_655 . . . ? C3 C2 C6 C5 -0.7(10) . . . . ? C1 C2 C6 C5 -179.1(6) . . . . ? N1 C5 C6 C2 0.6(10) . . . . ? _diffrn_measured_fraction_theta_max .999 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full .999 _refine_diff_density_max 1.611 _refine_diff_density_min -1.194 _refine_diff_density_rms .197