# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Wiley Youngs' _publ_contact_author_email YOUNGS@UAKRON.EDU _publ_section_title ; A theobromine derived silver N-heterocyclic carbene: synthesis, characterization, and antimicrobial efficacy studies on cystic fibrosis relevant pathogens ; loop_ _publ_author_name 'Wiley Youngs' 'Carolyn L. Cannon' 'Daniel S. Han' 'Khadijah M. Hindi' 'Matthew Panzner' 'Jane B. Taylor' ; B.D.Wright ; # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 737693' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1-(2-hydroxyethyl)-3,7,9-trimethylxanthinium iodide' _chemical_melting_point ? _chemical_formula_moiety 'C10 H15 N4 O3, I' _chemical_formula_sum 'C10 H15 I N4 O3' _chemical_formula_weight 366.16 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc 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 15.0967(18) _cell_length_b 10.4071(13) _cell_length_c 8.7080(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.119(2) _cell_angle_gamma 90.00 _cell_volume 1326.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2854 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3776 _exptl_absorpt_correction_T_max 0.6299 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10406 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.29 _reflns_number_total 2684 _reflns_number_gt 2299 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0605P)^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 2684 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 I1 I 0.355568(17) 0.88414(3) 0.20022(3) 0.02675(14) Uani 1 1 d . . . O1 O 0.2633(2) 0.2539(3) 0.7505(3) 0.0288(7) Uani 1 1 d . . . O2 O 0.1341(2) 0.5427(3) 0.4931(3) 0.0287(7) Uani 1 1 d . . . H2 H 0.1835 0.5672 0.5533 0.043 Uiso 1 1 calc R . . O3 O 0.04993(18) 0.5430(3) 0.8266(3) 0.0255(6) Uani 1 1 d . . . N1 N 0.1812(2) 0.6036(3) 1.1405(4) 0.0206(7) Uani 1 1 d . . . N2 N 0.3181(2) 0.5195(3) 1.2037(4) 0.0202(7) Uani 1 1 d . . . N3 N 0.3030(2) 0.3799(3) 0.9686(4) 0.0226(8) Uani 1 1 d . . . N4 N 0.1575(2) 0.3980(3) 0.7871(4) 0.0220(8) Uani 1 1 d . . . C1 C 0.2589(3) 0.6004(4) 1.2489(5) 0.0215(9) Uani 1 1 d . . . H1 H 0.2717 0.6480 1.3449 0.026 Uiso 1 1 calc R . . C2 C 0.2744(3) 0.4699(4) 1.0587(4) 0.0212(9) Uani 1 1 d . . . C3 C 0.2429(3) 0.3385(4) 0.8319(5) 0.0238(9) Uani 1 1 d . . . C4 C 0.1248(3) 0.4936(4) 0.8729(5) 0.0231(9) Uani 1 1 d . . . C5 C 0.1894(3) 0.5224(4) 1.0182(5) 0.0209(8) Uani 1 1 d . . . C6 C 0.1024(3) 0.6810(4) 1.1492(5) 0.0252(9) Uani 1 1 d . . . H6A H 0.1156 0.7282 1.2496 0.038 Uiso 1 1 calc R . . H6B H 0.0495 0.6249 1.1431 0.038 Uiso 1 1 calc R . . H6C H 0.0889 0.7420 1.0609 0.038 Uiso 1 1 calc R . . C7 C 0.4120(3) 0.5056(5) 1.2970(5) 0.0310(10) Uani 1 1 d . . . H7A H 0.4537 0.5442 1.2396 0.046 Uiso 1 1 calc R . . H7B H 0.4264 0.4142 1.3150 0.046 Uiso 1 1 calc R . . H7C H 0.4189 0.5492 1.3990 0.046 Uiso 1 1 calc R . . C8 C 0.3946(3) 0.3244(5) 1.0040(5) 0.0336(11) Uani 1 1 d . . . H8A H 0.4382 0.3857 1.0663 0.050 Uiso 1 1 calc R . . H8B H 0.4117 0.3054 0.9049 0.050 Uiso 1 1 calc R . . H8C H 0.3953 0.2450 1.0647 0.050 Uiso 1 1 calc R . . C9 C 0.0975(3) 0.3579(4) 0.6339(5) 0.0282(10) Uani 1 1 d . . . H9A H 0.0349 0.3902 0.6267 0.034 Uiso 1 1 calc R . . H9B H 0.0947 0.2629 0.6297 0.034 Uiso 1 1 calc R . . C10 C 0.1297(3) 0.4065(4) 0.4948(5) 0.0279(10) Uani 1 1 d . . . H10A H 0.1910 0.3708 0.4988 0.034 Uiso 1 1 calc R . . H10B H 0.0875 0.3763 0.3958 0.034 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 I1 0.0225(2) 0.0286(2) 0.0282(2) 0.00061(11) 0.00444(13) -0.00235(11) O1 0.0351(17) 0.0233(15) 0.0272(16) -0.0026(13) 0.0064(13) 0.0069(13) O2 0.0272(16) 0.0319(17) 0.0264(16) 0.0030(14) 0.0051(13) 0.0000(14) O3 0.0194(15) 0.0287(16) 0.0265(15) 0.0005(13) 0.0021(12) 0.0024(13) N1 0.0205(18) 0.0217(18) 0.0206(18) -0.0003(13) 0.0070(14) -0.0001(13) N2 0.0173(17) 0.0216(17) 0.0214(18) 0.0010(14) 0.0044(13) -0.0006(14) N3 0.0236(19) 0.0241(19) 0.0201(18) 0.0011(13) 0.0050(14) 0.0025(14) N4 0.0250(19) 0.0224(19) 0.0177(18) -0.0005(13) 0.0035(15) -0.0018(14) C1 0.021(2) 0.023(2) 0.020(2) -0.0017(16) 0.0053(16) -0.0035(16) C2 0.024(2) 0.019(2) 0.019(2) 0.0048(16) 0.0033(16) 0.0013(17) C3 0.029(2) 0.0171(19) 0.027(2) 0.0056(18) 0.0105(18) 0.0008(18) C4 0.028(2) 0.016(2) 0.024(2) 0.0024(17) 0.0056(18) -0.0059(17) C5 0.022(2) 0.0188(19) 0.022(2) -0.0007(16) 0.0065(16) -0.0034(16) C6 0.024(2) 0.026(2) 0.026(2) 0.0023(18) 0.0079(17) 0.0052(18) C7 0.023(2) 0.035(3) 0.030(2) -0.005(2) -0.0019(18) 0.0066(19) C8 0.030(2) 0.040(3) 0.028(2) -0.003(2) 0.0021(18) 0.014(2) C9 0.031(2) 0.024(2) 0.026(2) -0.0049(19) 0.0005(18) -0.0057(19) C10 0.029(2) 0.031(2) 0.020(2) -0.0047(18) -0.0022(17) 0.0044(19) _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 O1 C3 1.216(5) . ? O2 C10 1.419(5) . ? O2 H2 0.8400 . ? O3 C4 1.218(5) . ? N1 C1 1.314(5) . ? N1 C5 1.390(5) . ? N1 C6 1.454(5) . ? N2 C1 1.354(5) . ? N2 C2 1.375(5) . ? N2 C7 1.459(5) . ? N3 C2 1.358(5) . ? N3 C3 1.377(5) . ? N3 C8 1.461(5) . ? N4 C3 1.398(5) . ? N4 C4 1.404(5) . ? N4 C9 1.479(5) . ? C1 H1 0.9500 . ? C2 C5 1.360(5) . ? C4 C5 1.428(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.499(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 C10 O2 H2 109.5 . . ? C1 N1 C5 107.7(3) . . ? C1 N1 C6 125.1(4) . . ? C5 N1 C6 127.2(3) . . ? C1 N2 C2 107.3(3) . . ? C1 N2 C7 121.4(3) . . ? C2 N2 C7 131.1(3) . . ? C2 N3 C3 118.7(3) . . ? C2 N3 C8 124.6(4) . . ? C3 N3 C8 116.7(3) . . ? C3 N4 C4 125.9(3) . . ? C3 N4 C9 116.6(3) . . ? C4 N4 C9 117.5(3) . . ? N1 C1 N2 110.1(4) . . ? N1 C1 H1 124.9 . . ? N2 C1 H1 124.9 . . ? N3 C2 C5 122.7(4) . . ? N3 C2 N2 129.9(4) . . ? C5 C2 N2 107.3(3) . . ? O1 C3 N3 121.6(4) . . ? O1 C3 N4 120.4(4) . . ? N3 C3 N4 118.0(4) . . ? O3 C4 N4 122.8(4) . . ? O3 C4 C5 125.7(4) . . ? N4 C4 C5 111.5(4) . . ? C2 C5 N1 107.5(3) . . ? C2 C5 C4 122.9(4) . . ? N1 C5 C4 129.6(4) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C9 C10 112.6(4) . . ? N4 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N4 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? O2 C10 C9 111.8(4) . . ? O2 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? O2 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? 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 C5 N1 C1 N2 -0.5(4) . . . . ? C6 N1 C1 N2 -179.6(4) . . . . ? C2 N2 C1 N1 0.1(4) . . . . ? C7 N2 C1 N1 175.2(4) . . . . ? C3 N3 C2 C5 -1.1(6) . . . . ? C8 N3 C2 C5 177.5(4) . . . . ? C3 N3 C2 N2 174.7(4) . . . . ? C8 N3 C2 N2 -6.6(7) . . . . ? C1 N2 C2 N3 -176.1(4) . . . . ? C7 N2 C2 N3 9.5(7) . . . . ? C1 N2 C2 C5 0.3(4) . . . . ? C7 N2 C2 C5 -174.1(4) . . . . ? C2 N3 C3 O1 -176.5(4) . . . . ? C8 N3 C3 O1 4.7(6) . . . . ? C2 N3 C3 N4 4.4(5) . . . . ? C8 N3 C3 N4 -174.3(4) . . . . ? C4 N4 C3 O1 177.9(4) . . . . ? C9 N4 C3 O1 -3.4(6) . . . . ? C4 N4 C3 N3 -3.1(6) . . . . ? C9 N4 C3 N3 175.6(4) . . . . ? C3 N4 C4 O3 179.1(4) . . . . ? C9 N4 C4 O3 0.4(6) . . . . ? C3 N4 C4 C5 -1.6(6) . . . . ? C9 N4 C4 C5 179.7(3) . . . . ? N3 C2 C5 N1 176.1(4) . . . . ? N2 C2 C5 N1 -0.6(4) . . . . ? N3 C2 C5 C4 -4.0(6) . . . . ? N2 C2 C5 C4 179.3(4) . . . . ? C1 N1 C5 C2 0.7(4) . . . . ? C6 N1 C5 C2 179.7(4) . . . . ? C1 N1 C5 C4 -179.2(4) . . . . ? C6 N1 C5 C4 -0.2(7) . . . . ? O3 C4 C5 C2 -175.7(4) . . . . ? N4 C4 C5 C2 5.1(5) . . . . ? O3 C4 C5 N1 4.2(7) . . . . ? N4 C4 C5 N1 -175.1(4) . . . . ? C3 N4 C9 C10 -71.9(5) . . . . ? C4 N4 C9 C10 106.9(4) . . . . ? N4 C9 C10 O2 -59.5(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.963 _refine_diff_density_min -1.374 _refine_diff_density_rms 0.142 # Attachment 'SCC8.cif' data_SCC8 _database_code_depnum_ccdc_archive 'CCDC 737694' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;1-(2-hydroxyethyl)-3,7,9-trimethylxanthin-8-ylidene silver acetate ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H17 Ag N4 O5' _chemical_formula_sum 'C12 H17 Ag N4 O5' _chemical_formula_weight 405.17 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.896(3) _cell_length_b 8.2797(11) _cell_length_c 14.8598(19) _cell_angle_alpha 90.00 _cell_angle_beta 94.104(2) _cell_angle_gamma 90.00 _cell_volume 2932.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2602 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.77 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.835 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 1.405 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5834 _exptl_absorpt_correction_T_max 0.9081 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11365 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 26.30 _reflns_number_total 2985 _reflns_number_gt 2407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0509P)^2^+4.6727P] 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 2985 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 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 -0.056017(12) 0.49034(3) 0.052592(19) 0.02372(12) Uani 1 1 d . . . O1 O 0.22070(12) 0.4522(3) 0.3583(2) 0.0324(7) Uani 1 1 d . . . O2 O 0.12159(11) 0.1138(3) 0.48671(19) 0.0312(7) Uani 1 1 d . . . H2 H 0.1191 0.0126 0.4866 0.047 Uiso 1 1 calc R . . O3 O 0.10510(12) 0.0352(3) 0.26262(19) 0.0265(6) Uani 1 1 d . . . O4 O -0.13135(12) 0.5299(3) -0.02829(19) 0.0289(6) Uani 1 1 d . . . O5 O -0.11528(13) 0.7813(3) 0.01889(19) 0.0365(7) Uani 1 1 d . . . N1 N 0.03414(12) 0.2888(3) 0.1590(2) 0.0194(7) Uani 1 1 d . . . N2 N 0.05316(13) 0.5451(4) 0.1742(2) 0.0200(7) Uani 1 1 d . . . N3 N 0.14276(14) 0.5192(3) 0.2693(2) 0.0214(7) Uani 1 1 d . . . N4 N 0.16032(13) 0.2472(4) 0.3164(2) 0.0230(7) Uani 1 1 d . . . C1 C 0.01551(16) 0.4352(5) 0.1338(2) 0.0212(8) Uani 1 1 d . . . C2 C 0.09559(16) 0.4625(4) 0.2214(2) 0.0206(8) Uani 1 1 d . . . C3 C 0.17736(16) 0.4103(4) 0.3178(3) 0.0248(8) Uani 1 1 d . . . C4 C 0.11526(15) 0.1811(4) 0.2634(3) 0.0215(8) Uani 1 1 d . . . C5 C 0.08327(15) 0.3018(4) 0.2140(2) 0.0189(8) Uani 1 1 d . . . C6 C 0.00950(16) 0.1368(4) 0.1237(3) 0.0249(9) Uani 1 1 d . . . H6A H -0.0269 0.1588 0.0916 0.037 Uiso 1 1 calc R . . H6B H 0.0044 0.0627 0.1739 0.037 Uiso 1 1 calc R . . H6C H 0.0346 0.0875 0.0822 0.037 Uiso 1 1 calc R . . C7 C 0.04792(17) 0.7198(4) 0.1574(3) 0.0287(9) Uani 1 1 d . . . H7A H 0.0546 0.7784 0.2145 0.043 Uiso 1 1 calc R . . H7B H 0.0101 0.7440 0.1311 0.043 Uiso 1 1 calc R . . H7C H 0.0756 0.7535 0.1155 0.043 Uiso 1 1 calc R . . C8 C 0.16224(18) 0.6882(4) 0.2653(3) 0.0308(10) Uani 1 1 d . . . H8A H 0.1591 0.7255 0.2025 0.046 Uiso 1 1 calc R . . H8B H 0.2015 0.6947 0.2891 0.046 Uiso 1 1 calc R . . H8C H 0.1391 0.7566 0.3016 0.046 Uiso 1 1 calc R . . C9 C 0.19447(16) 0.1386(4) 0.3787(3) 0.0260(9) Uani 1 1 d . . . H9A H 0.2348 0.1640 0.3756 0.031 Uiso 1 1 calc R . . H9B H 0.1885 0.0249 0.3597 0.031 Uiso 1 1 calc R . . C10 C 0.17811(16) 0.1595(4) 0.4757(3) 0.0265(9) Uani 1 1 d . . . H10A H 0.2034 0.0932 0.5164 0.032 Uiso 1 1 calc R . . H10B H 0.1834 0.2740 0.4937 0.032 Uiso 1 1 calc R . . C11 C -0.14362(17) 0.6796(5) -0.0265(3) 0.0310(10) Uani 1 1 d . . . C12 C -0.19562(19) 0.7310(7) -0.0838(3) 0.0514(14) Uani 1 1 d . . . H12A H -0.2278 0.7335 -0.0465 0.077 Uiso 1 1 calc R . . H12B H -0.2029 0.6539 -0.1332 0.077 Uiso 1 1 calc R . . H12C H -0.1897 0.8388 -0.1086 0.077 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 0.02428(19) 0.02358(18) 0.02234(19) 0.00153(12) -0.00497(12) 0.00334(12) O1 0.0293(16) 0.0238(14) 0.0414(17) 0.0054(13) -0.0164(14) -0.0058(12) O2 0.0291(16) 0.0290(15) 0.0344(16) 0.0004(13) -0.0044(13) -0.0009(12) O3 0.0305(16) 0.0166(13) 0.0308(16) 0.0013(11) -0.0091(12) -0.0023(11) O4 0.0235(15) 0.0328(16) 0.0293(16) 0.0033(12) -0.0049(12) 0.0025(12) O5 0.0432(19) 0.0309(16) 0.0344(17) -0.0027(13) -0.0047(14) 0.0124(14) N1 0.0200(17) 0.0179(15) 0.0195(16) -0.0010(12) -0.0038(13) -0.0006(12) N2 0.0252(18) 0.0159(14) 0.0184(16) 0.0003(13) -0.0013(13) 0.0030(12) N3 0.0224(17) 0.0152(15) 0.0260(18) 0.0004(12) -0.0030(14) -0.0021(12) N4 0.0247(18) 0.0155(15) 0.0272(18) 0.0018(13) -0.0077(14) -0.0008(13) C1 0.024(2) 0.0226(18) 0.0162(18) 0.0007(15) -0.0005(15) 0.0028(16) C2 0.024(2) 0.0186(17) 0.0183(19) -0.0011(15) -0.0016(15) 0.0036(15) C3 0.023(2) 0.0211(19) 0.030(2) 0.0017(16) -0.0059(17) -0.0042(16) C4 0.021(2) 0.0201(18) 0.023(2) -0.0021(15) -0.0009(16) -0.0007(15) C5 0.021(2) 0.0170(17) 0.0179(19) -0.0031(14) -0.0044(15) -0.0015(14) C6 0.028(2) 0.0185(18) 0.028(2) -0.0010(16) -0.0044(17) -0.0024(16) C7 0.037(2) 0.0153(18) 0.032(2) -0.0013(16) -0.0090(19) 0.0035(16) C8 0.033(2) 0.0154(18) 0.042(3) 0.0027(17) -0.0093(19) -0.0061(17) C9 0.024(2) 0.0179(18) 0.034(2) 0.0021(16) -0.0116(17) 0.0029(15) C10 0.027(2) 0.0195(18) 0.031(2) 0.0017(16) -0.0118(18) 0.0001(16) C11 0.028(2) 0.040(2) 0.025(2) 0.0065(19) 0.0047(18) 0.0130(19) C12 0.036(3) 0.084(4) 0.034(3) 0.006(3) 0.001(2) 0.034(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 C1 2.072(4) . ? Ag1 O4 2.117(3) . ? Ag1 Ag1 3.1992(7) 5_565 ? O1 C3 1.210(4) . ? O2 C10 1.423(4) . ? O2 H2 0.8400 . ? O3 C4 1.232(4) . ? O4 C11 1.274(5) . ? O5 C11 1.248(5) . ? N1 C1 1.335(5) . ? N1 C5 1.386(5) . ? N1 C6 1.470(4) . ? N2 C2 1.374(5) . ? N2 C1 1.386(5) . ? N2 C7 1.472(5) . ? N3 C2 1.372(5) . ? N3 C3 1.390(5) . ? N3 C8 1.477(4) . ? N4 C4 1.399(5) . ? N4 C3 1.411(5) . ? N4 C9 1.491(4) . ? C2 C5 1.365(5) . ? C4 C5 1.429(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.530(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 C1 Ag1 O4 175.86(12) . . ? C1 Ag1 Ag1 67.13(10) . 5_565 ? O4 Ag1 Ag1 114.97(8) . 5_565 ? C10 O2 H2 109.5 . . ? C11 O4 Ag1 109.0(3) . . ? C1 N1 C5 110.2(3) . . ? C1 N1 C6 124.1(3) . . ? C5 N1 C6 125.3(3) . . ? C2 N2 C1 109.1(3) . . ? C2 N2 C7 128.8(3) . . ? C1 N2 C7 121.9(3) . . ? C2 N3 C3 118.9(3) . . ? C2 N3 C8 123.6(3) . . ? C3 N3 C8 117.3(3) . . ? C4 N4 C3 126.3(3) . . ? C4 N4 C9 118.6(3) . . ? C3 N4 C9 115.1(3) . . ? N1 C1 N2 106.4(3) . . ? N1 C1 Ag1 127.4(3) . . ? N2 C1 Ag1 126.2(3) . . ? C5 C2 N2 107.3(3) . . ? C5 C2 N3 122.7(3) . . ? N2 C2 N3 130.0(3) . . ? O1 C3 N3 121.9(3) . . ? O1 C3 N4 121.1(3) . . ? N3 C3 N4 117.0(3) . . ? O3 C4 N4 122.1(3) . . ? O3 C4 C5 125.7(3) . . ? N4 C4 C5 112.2(3) . . ? C2 C5 N1 107.0(3) . . ? C2 C5 C4 122.4(3) . . ? N1 C5 C4 130.4(3) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C9 C10 110.6(3) . . ? N4 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N4 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? O2 C10 C9 112.7(3) . . ? O2 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? O2 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? O5 C11 O4 123.4(4) . . ? O5 C11 C12 120.4(4) . . ? O4 C11 C12 116.2(4) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 Ag1 Ag1 O4 C11 -91.7(3) 5_565 . . . ? C5 N1 C1 N2 -0.5(4) . . . . ? C6 N1 C1 N2 -173.6(3) . . . . ? C5 N1 C1 Ag1 -179.6(3) . . . . ? C6 N1 C1 Ag1 7.4(5) . . . . ? C2 N2 C1 N1 1.9(4) . . . . ? C7 N2 C1 N1 176.4(3) . . . . ? C2 N2 C1 Ag1 -179.0(3) . . . . ? C7 N2 C1 Ag1 -4.5(5) . . . . ? Ag1 Ag1 C1 N1 -101.4(3) 5_565 . . . ? Ag1 Ag1 C1 N2 79.7(3) 5_565 . . . ? C1 N2 C2 C5 -2.6(4) . . . . ? C7 N2 C2 C5 -176.6(4) . . . . ? C1 N2 C2 N3 177.7(4) . . . . ? C7 N2 C2 N3 3.7(7) . . . . ? C3 N3 C2 C5 -4.9(6) . . . . ? C8 N3 C2 C5 168.8(4) . . . . ? C3 N3 C2 N2 174.7(4) . . . . ? C8 N3 C2 N2 -11.6(6) . . . . ? C2 N3 C3 O1 176.9(4) . . . . ? C8 N3 C3 O1 2.8(6) . . . . ? C2 N3 C3 N4 -1.9(5) . . . . ? C8 N3 C3 N4 -175.9(3) . . . . ? C4 N4 C3 O1 -171.4(4) . . . . ? C9 N4 C3 O1 8.9(6) . . . . ? C4 N4 C3 N3 7.4(6) . . . . ? C9 N4 C3 N3 -172.3(3) . . . . ? C3 N4 C4 O3 175.9(4) . . . . ? C9 N4 C4 O3 -4.4(6) . . . . ? C3 N4 C4 C5 -5.4(5) . . . . ? C9 N4 C4 C5 174.3(3) . . . . ? N2 C2 C5 N1 2.2(4) . . . . ? N3 C2 C5 N1 -178.1(3) . . . . ? N2 C2 C5 C4 -172.8(3) . . . . ? N3 C2 C5 C4 6.9(6) . . . . ? C1 N1 C5 C2 -1.1(4) . . . . ? C6 N1 C5 C2 171.9(3) . . . . ? C1 N1 C5 C4 173.4(4) . . . . ? C6 N1 C5 C4 -13.7(6) . . . . ? O3 C4 C5 C2 176.9(4) . . . . ? N4 C4 C5 C2 -1.7(5) . . . . ? O3 C4 C5 N1 3.2(7) . . . . ? N4 C4 C5 N1 -175.5(4) . . . . ? C4 N4 C9 C10 -101.8(4) . . . . ? C3 N4 C9 C10 77.9(4) . . . . ? N4 C9 C10 O2 63.4(4) . . . . ? Ag1 O4 C11 O5 -1.9(5) . . . . ? Ag1 O4 C11 C12 177.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.30 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.160 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.122