# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Shuang Wang' _publ_contact_author_email anitawsss@yahoo.com.cn loop_ _publ_author_name 'Shuang Wang' 'Hongying Zang' 'Chunyi Sun' 'Guangjuan Xu' ; Xinlong Wang ; 'Kuizhan Shao' 'Zhongmin Su' data_mm _database_code_depnum_ccdc_archive 'CCDC 774545' #TrackingRef '- 74545-774546.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 Ag N9 O3' _chemical_formula_sum 'C20 H18 Ag N9 O3' _chemical_formula_weight 540.30 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' _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 14.696(5) _cell_length_b 14.296(5) _cell_length_c 11.558(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 121.509(5) _cell_angle_gamma 90.000(5) _cell_volume 2070.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 'total reflection' _cell_measurement_theta_min 1.33 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.019 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.650 _exptl_absorpt_correction_T_max 0.783 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 6195 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2417 _reflns_number_gt 2038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0290P)^2^+2.3525P] 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 2417 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0750 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _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 0.0000 0.29197(2) 0.2500 0.05788(12) Uani 1 2 d S . . N1 N 0.08612(14) 0.23451(13) 0.13923(19) 0.0372(4) Uani 1 1 d . . . N3 N 0.16891(13) 0.28536(12) 0.15191(17) 0.0315(4) Uani 1 1 d . . . N4 N 0.21976(13) 0.39384(12) 0.33154(17) 0.0320(4) Uani 1 1 d . . . C7 C 0.18189(15) 0.38385(14) 0.1879(2) 0.0300(4) Uani 1 1 d . . . H7 H 0.2394 0.4069 0.1763 0.036 Uiso 1 1 calc R . . N5 N 0.5000 0.3757(3) 0.2500 0.0524(7) Uani 1 2 d S . . N2 N 0.15678(15) 0.37373(15) 0.38178(19) 0.0426(4) Uani 1 1 d . . . C8 C 0.08353(15) 0.44181(14) 0.09291(19) 0.0294(4) Uani 1 1 d . . . C1 C 0.10276(18) 0.14885(16) 0.1091(2) 0.0421(5) Uani 1 1 d . . . H1 H 0.0585 0.0980 0.0945 0.051 Uiso 1 1 calc R . . C2 C 0.1944(2) 0.14457(17) 0.1021(3) 0.0465(5) Uani 1 1 d . . . H2 H 0.2215 0.0928 0.0813 0.056 Uiso 1 1 calc R . . C6 C 0.32168(17) 0.40849(16) 0.4315(2) 0.0423(5) Uani 1 1 d . . . H6 H 0.3789 0.4213 0.4208 0.051 Uiso 1 1 calc R . . C10 C -0.05623(16) 0.47864(15) -0.1365(2) 0.0341(4) Uani 1 1 d . . . H10 H -0.0937 0.4638 -0.2284 0.041 Uiso 1 1 calc R . . O1 O 0.43273(19) 0.4189(2) 0.2606(3) 0.0897(8) Uani 1 1 d . . . O2 O 0.5000 0.2898(2) 0.2500 0.0977(12) Uani 1 2 d S . . C9 C 0.02605(16) 0.42079(15) -0.0453(2) 0.0347(4) Uani 1 1 d . . . H9 H 0.0430 0.3676 -0.0766 0.042 Uiso 1 1 calc R . . C3 C 0.23570(18) 0.23280(16) 0.1323(2) 0.0398(5) Uani 1 1 d . . . H3 H 0.2982 0.2529 0.1382 0.048 Uiso 1 1 calc R . . C4 C 0.2219(2) 0.37876(18) 0.5153(2) 0.0476(6) Uani 1 1 d . . . H4 H 0.2008 0.3686 0.5773 0.057 Uiso 1 1 calc R . . C5 C 0.3252(2) 0.40103(18) 0.5512(2) 0.0511(6) Uani 1 1 d . . . H5 H 0.3842 0.4091 0.6382 0.061 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 0.03886(16) 0.0649(2) 0.0844(2) 0.000 0.04230(16) 0.000 N1 0.0285(8) 0.0395(9) 0.0430(10) -0.0022(8) 0.0182(8) -0.0035(7) N3 0.0278(8) 0.0353(9) 0.0325(8) 0.0008(7) 0.0166(7) 0.0013(7) N4 0.0269(8) 0.0371(9) 0.0297(9) 0.0013(7) 0.0131(7) 0.0008(7) C7 0.0269(9) 0.0336(10) 0.0316(10) 0.0001(8) 0.0169(8) -0.0011(8) N5 0.0359(14) 0.075(2) 0.0472(17) 0.000 0.0222(13) 0.000 N2 0.0355(9) 0.0617(12) 0.0359(10) 0.0008(9) 0.0224(8) 0.0022(9) C8 0.0267(9) 0.0328(10) 0.0292(10) 0.0025(8) 0.0150(8) -0.0011(8) C1 0.0392(11) 0.0388(11) 0.0406(12) -0.0023(9) 0.0153(10) -0.0016(9) C2 0.0468(13) 0.0409(12) 0.0505(14) -0.0037(10) 0.0246(11) 0.0076(10) C6 0.0286(10) 0.0491(13) 0.0378(12) 0.0011(10) 0.0094(9) -0.0020(9) C10 0.0344(10) 0.0386(11) 0.0255(9) -0.0023(8) 0.0131(8) 0.0000(9) O1 0.0675(14) 0.129(2) 0.0963(17) 0.0330(15) 0.0590(13) 0.0423(14) O2 0.088(3) 0.071(2) 0.102(3) 0.000 0.027(2) 0.000 C9 0.0379(11) 0.0337(10) 0.0324(10) -0.0015(8) 0.0182(9) 0.0033(9) C3 0.0349(11) 0.0470(12) 0.0414(12) 0.0001(10) 0.0227(10) 0.0064(9) C4 0.0569(15) 0.0554(14) 0.0354(12) 0.0035(10) 0.0275(11) 0.0098(12) C5 0.0448(13) 0.0604(16) 0.0309(11) 0.0016(11) 0.0079(10) 0.0036(11) _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 N2 2.308(2) . ? Ag1 N2 2.308(2) 2 ? Ag1 N1 2.368(2) . ? Ag1 N1 2.368(2) 2 ? N1 C1 1.330(3) . ? N1 N3 1.358(2) . ? N3 C3 1.346(3) . ? N3 C7 1.452(3) . ? N4 C6 1.347(3) . ? N4 N2 1.356(2) . ? N4 C7 1.456(3) . ? C7 C8 1.524(3) . ? C7 H7 0.9800 . ? N5 O1 1.224(3) 2_655 ? N5 O1 1.224(3) . ? N5 O2 1.228(4) . ? N2 C4 1.326(3) . ? C8 C10 1.385(3) 5_565 ? C8 C9 1.395(3) . ? C1 C2 1.392(3) . ? C1 H1 0.9300 . ? C2 C3 1.364(3) . ? C2 H2 0.9300 . ? C6 C5 1.361(4) . ? C6 H6 0.9300 . ? C10 C8 1.385(3) 5_565 ? C10 C9 1.387(3) . ? C10 H10 0.9300 . ? C9 H9 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.386(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? 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 N2 Ag1 N2 119.14(11) . 2 ? N2 Ag1 N1 84.33(7) . . ? N2 Ag1 N1 116.75(7) 2 . ? N2 Ag1 N1 116.75(7) . 2 ? N2 Ag1 N1 84.33(7) 2 2 ? N1 Ag1 N1 139.42(9) . 2 ? C1 N1 N3 104.13(18) . . ? C1 N1 Ag1 133.15(16) . . ? N3 N1 Ag1 117.25(13) . . ? C3 N3 N1 111.97(17) . . ? C3 N3 C7 126.25(18) . . ? N1 N3 C7 121.74(16) . . ? C6 N4 N2 111.56(18) . . ? C6 N4 C7 125.78(18) . . ? N2 N4 C7 121.85(16) . . ? N3 C7 N4 109.67(16) . . ? N3 C7 C8 112.81(16) . . ? N4 C7 C8 114.94(16) . . ? N3 C7 H7 106.3 . . ? N4 C7 H7 106.3 . . ? C8 C7 H7 106.3 . . ? O1 N5 O1 119.5(4) 2_655 . ? O1 N5 O2 120.2(2) 2_655 . ? O1 N5 O2 120.2(2) . . ? C4 N2 N4 104.35(18) . . ? C4 N2 Ag1 131.29(17) . . ? N4 N2 Ag1 119.62(13) . . ? C10 C8 C9 118.44(18) 5_565 . ? C10 C8 C7 122.01(18) 5_565 . ? C9 C8 C7 119.12(17) . . ? N1 C1 C2 111.8(2) . . ? N1 C1 H1 124.1 . . ? C2 C1 H1 124.1 . . ? C3 C2 C1 105.0(2) . . ? C3 C2 H2 127.5 . . ? C1 C2 H2 127.5 . . ? N4 C6 C5 107.1(2) . . ? N4 C6 H6 126.4 . . ? C5 C6 H6 126.4 . . ? C8 C10 C9 121.07(19) 5_565 . ? C8 C10 H10 119.5 5_565 . ? C9 C10 H10 119.5 . . ? C10 C9 C8 120.48(19) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? N3 C3 C2 107.0(2) . . ? N3 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? N2 C4 C5 111.9(2) . . ? N2 C4 H4 124.1 . . ? C5 C4 H4 124.1 . . ? C6 C5 C4 105.0(2) . . ? C6 C5 H5 127.5 . . ? C4 C5 H5 127.5 . . ? 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 N2 Ag1 N1 C1 128.3(2) . . . . ? N2 Ag1 N1 C1 -111.8(2) 2 . . . ? N1 Ag1 N1 C1 2.90(19) 2 . . . ? N2 Ag1 N1 N3 -20.94(14) . . . . ? N2 Ag1 N1 N3 98.93(15) 2 . . . ? N1 Ag1 N1 N3 -146.34(15) 2 . . . ? C1 N1 N3 C3 -0.9(2) . . . . ? Ag1 N1 N3 C3 156.50(14) . . . . ? C1 N1 N3 C7 -178.62(18) . . . . ? Ag1 N1 N3 C7 -21.2(2) . . . . ? C3 N3 C7 N4 -102.9(2) . . . . ? N1 N3 C7 N4 74.5(2) . . . . ? C3 N3 C7 C8 127.6(2) . . . . ? N1 N3 C7 C8 -55.0(2) . . . . ? C6 N4 C7 N3 99.1(2) . . . . ? N2 N4 C7 N3 -69.7(2) . . . . ? C6 N4 C7 C8 -132.6(2) . . . . ? N2 N4 C7 C8 58.6(2) . . . . ? C6 N4 N2 C4 1.6(2) . . . . ? C7 N4 N2 C4 171.82(19) . . . . ? C6 N4 N2 Ag1 -156.68(15) . . . . ? C7 N4 N2 Ag1 13.6(2) . . . . ? N2 Ag1 N2 C4 115.6(2) 2 . . . ? N1 Ag1 N2 C4 -126.9(2) . . . . ? N1 Ag1 N2 C4 16.7(2) 2 . . . ? N2 Ag1 N2 N4 -92.93(16) 2 . . . ? N1 Ag1 N2 N4 24.62(16) . . . . ? N1 Ag1 N2 N4 168.20(14) 2 . . . ? N3 C7 C8 C10 149.71(19) . . . 5_565 ? N4 C7 C8 C10 23.0(3) . . . 5_565 ? N3 C7 C8 C9 -37.8(2) . . . . ? N4 C7 C8 C9 -164.56(18) . . . . ? N3 N1 C1 C2 -0.2(3) . . . . ? Ag1 N1 C1 C2 -152.22(17) . . . . ? N1 C1 C2 C3 1.1(3) . . . . ? N2 N4 C6 C5 -2.2(3) . . . . ? C7 N4 C6 C5 -171.9(2) . . . . ? C8 C10 C9 C8 -0.2(3) 5_565 . . . ? C10 C8 C9 C10 0.2(3) 5_565 . . . ? C7 C8 C9 C10 -172.53(18) . . . . ? N1 N3 C3 C2 1.6(3) . . . . ? C7 N3 C3 C2 179.22(19) . . . . ? C1 C2 C3 N3 -1.6(3) . . . . ? N4 N2 C4 C5 -0.4(3) . . . . ? Ag1 N2 C4 C5 154.22(19) . . . . ? N4 C6 C5 C4 1.8(3) . . . . ? N2 C4 C5 C6 -0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.324 _refine_diff_density_min -0.884 _refine_diff_density_rms 0.109 data_11 _database_code_depnum_ccdc_archive 'CCDC 774546' #TrackingRef '- 74545-774546.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 Ag N9 O3' _chemical_formula_sum 'C20 H18 Ag N9 O3' _chemical_formula_weight 540.30 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.155(5) _cell_length_b 20.337(5) _cell_length_c 11.698(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 91.470(5) _cell_angle_gamma 90.000(5) _cell_volume 2177.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 'total reflection' _cell_measurement_theta_min 1.33 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.969 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.665 _exptl_absorpt_correction_T_max 0.793 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 5507 _diffrn_reflns_av_R_equivalents 0.1022 _diffrn_reflns_av_sigmaI/netI 0.1119 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3511 _reflns_number_gt 1790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1074P)^2^+7.1167P] 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 3511 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1516 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.2302 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.004 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 0.70967(10) 0.15870(5) 0.47078(7) 0.0680(4) Uani 1 1 d . . . N5 N 0.8360(9) 0.1091(4) 0.7167(6) 0.047(2) Uani 1 1 d . . . C17 C 0.9743(9) 0.1095(5) 0.6602(7) 0.042(2) Uani 1 1 d . . . H17 H 1.0486 0.0994 0.7195 0.051 Uiso 1 1 calc R . . N8 N 0.9295(9) 0.2018(4) 0.5318(7) 0.053(2) Uani 1 1 d . . . N6 N 0.7095(8) 0.1181(4) 0.6565(6) 0.050(2) Uani 1 1 d . . . N2 N 0.7499(9) 0.1128(5) 0.2864(7) 0.056(2) Uani 1 1 d . . . N7 N 1.0105(8) 0.1732(4) 0.6170(7) 0.048(2) Uani 1 1 d . . . C7 C 0.4977(10) 0.0776(5) 0.2909(7) 0.048(2) Uani 1 1 d . . . H7 H 0.4320 0.0533 0.2386 0.058 Uiso 1 1 calc R . . C20 C 0.9615(10) -0.0618(5) 0.5344(8) 0.054(3) Uani 1 1 d . . . H20 H 0.9336 -0.1035 0.5580 0.065 Uiso 1 1 calc R . . N1 N 0.6381(8) 0.0799(4) 0.2369(6) 0.047(2) Uani 1 1 d . . . C9 C 0.6029(10) -0.0109(5) 0.4188(7) 0.046(2) Uani 1 1 d . . . H9 H 0.6725 -0.0193 0.3641 0.056 Uiso 1 1 calc R . . C10 C 0.6005(9) -0.0494(5) 0.5171(7) 0.043(2) Uani 1 1 d . . . H10 H 0.6700 -0.0823 0.5278 0.052 Uiso 1 1 calc R . . N3 N 0.4346(9) 0.1415(4) 0.3042(6) 0.049(2) Uani 1 1 d . . . C18 C 0.9823(10) 0.0534(5) 0.5720(8) 0.045(2) Uani 1 1 d . . . N4 N 0.4899(9) 0.1841(4) 0.3840(6) 0.051(2) Uani 1 1 d . . . C8 C 0.5035(9) 0.0395(5) 0.4010(7) 0.041(2) Uani 1 1 d . . . C19 C 0.9459(10) -0.0089(5) 0.6068(8) 0.050(2) Uani 1 1 d . . . H19 H 0.9104 -0.0155 0.6797 0.061 Uiso 1 1 calc R . . C6 C 0.8591(12) 0.1027(6) 0.2166(9) 0.066(3) Uani 1 1 d . . . H6 H 0.9519 0.1205 0.2279 0.080 Uiso 1 1 calc R . . C16 C 0.6061(11) 0.1125(5) 0.7334(9) 0.057(3) Uani 1 1 d . . . H16 H 0.5064 0.1164 0.7175 0.068 Uiso 1 1 calc R . . C2 C 0.2931(12) 0.2267(6) 0.2982(9) 0.066(3) Uani 1 1 d . . . H2 H 0.2183 0.2560 0.2797 0.079 Uiso 1 1 calc R . . C11 C 1.1237(11) 0.2129(6) 0.6510(9) 0.062(3) Uani 1 1 d . . . H11 H 1.1938 0.2040 0.7078 0.075 Uiso 1 1 calc R . . C12 C 1.1142(13) 0.2681(6) 0.5860(9) 0.067(3) Uani 1 1 d . . . H12 H 1.1758 0.3044 0.5890 0.080 Uiso 1 1 calc R . . C14 C 0.8148(13) 0.0984(6) 0.8285(8) 0.061(3) Uani 1 1 d . . . H14 H 0.8862 0.0915 0.8852 0.073 Uiso 1 1 calc R . . O3 O 0.8459(12) 0.4182(5) 0.5125(8) 0.103(3) Uani 1 1 d . . . N9 N 0.7401(12) 0.3989(6) 0.4536(11) 0.079(3) Uani 1 1 d . . . C13 C 0.9948(12) 0.2590(5) 0.5149(10) 0.061(3) Uani 1 1 d . . . H13 H 0.9630 0.2896 0.4607 0.073 Uiso 1 1 calc R . . C1 C 0.3136(10) 0.1668(6) 0.2503(8) 0.054(3) Uani 1 1 d . . . H1 H 0.2569 0.1471 0.1928 0.064 Uiso 1 1 calc R . . C5 C 0.8208(14) 0.0632(7) 0.1259(9) 0.076(4) Uani 1 1 d . . . H5 H 0.8799 0.0496 0.0669 0.091 Uiso 1 1 calc R . . C3 C 0.4024(13) 0.2362(6) 0.3785(9) 0.065(3) Uani 1 1 d . . . H3 H 0.4138 0.2739 0.4230 0.078 Uiso 1 1 calc R . . C15 C 0.6680(14) 0.0998(6) 0.8416(9) 0.067(3) Uani 1 1 d . . . H15 H 0.6184 0.0936 0.9091 0.080 Uiso 1 1 calc R . . C4 C 0.6786(15) 0.0483(6) 0.1405(8) 0.069(3) Uani 1 1 d . . . H4 H 0.6200 0.0216 0.0937 0.083 Uiso 1 1 calc R . . O1 O 0.7613(13) 0.3858(6) 0.3536(9) 0.126(4) Uani 1 1 d . . . O2 O 0.6247(12) 0.3933(7) 0.4959(13) 0.162(6) Uani 1 1 d . . . 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 0.0741(7) 0.0787(7) 0.0502(5) -0.0016(5) -0.0176(4) -0.0010(5) N5 0.063(5) 0.050(5) 0.028(4) -0.014(4) 0.004(4) 0.000(4) C17 0.043(5) 0.048(6) 0.036(5) 0.007(4) -0.004(4) -0.007(5) N8 0.066(6) 0.041(5) 0.050(5) 0.001(4) -0.005(4) 0.003(4) N6 0.043(5) 0.068(6) 0.039(4) -0.010(4) -0.008(4) -0.002(4) N2 0.047(5) 0.081(7) 0.041(4) 0.006(4) 0.006(4) -0.004(5) N7 0.049(5) 0.049(5) 0.047(5) -0.007(4) 0.005(4) -0.003(4) C7 0.050(6) 0.063(7) 0.032(5) -0.002(5) 0.000(4) 0.004(5) C20 0.048(6) 0.053(6) 0.062(7) 0.009(5) 0.010(5) 0.002(5) N1 0.053(5) 0.055(5) 0.032(4) 0.004(4) -0.001(4) 0.008(4) C9 0.048(5) 0.053(6) 0.039(5) 0.004(4) 0.005(4) 0.000(5) C10 0.040(5) 0.047(6) 0.043(5) 0.012(4) 0.000(4) 0.009(4) N3 0.052(5) 0.061(6) 0.033(4) 0.005(4) 0.000(4) 0.016(4) C18 0.040(5) 0.053(6) 0.042(5) 0.000(5) -0.001(4) 0.006(5) N4 0.067(5) 0.048(5) 0.038(4) 0.001(4) 0.008(4) 0.007(4) C8 0.035(5) 0.047(6) 0.040(5) 0.003(4) -0.005(4) 0.001(4) C19 0.060(6) 0.056(6) 0.036(5) 0.006(5) 0.006(4) 0.002(5) C6 0.050(6) 0.101(10) 0.048(6) 0.015(7) 0.007(5) 0.013(6) C16 0.052(6) 0.060(7) 0.059(7) -0.010(5) 0.013(5) -0.004(5) C2 0.067(8) 0.071(8) 0.060(7) 0.018(6) 0.003(6) 0.020(6) C11 0.053(6) 0.086(9) 0.048(6) -0.014(6) 0.007(5) -0.009(6) C12 0.087(9) 0.054(7) 0.060(7) -0.015(6) 0.017(6) -0.021(7) C14 0.071(8) 0.069(8) 0.042(6) -0.001(5) -0.001(5) 0.003(6) O3 0.127(8) 0.099(7) 0.081(6) 0.024(6) -0.024(6) -0.014(7) N9 0.071(8) 0.077(8) 0.087(8) 0.008(6) -0.019(7) 0.010(6) C13 0.070(7) 0.048(7) 0.065(7) -0.011(5) 0.013(6) -0.008(6) C1 0.048(6) 0.068(7) 0.045(5) 0.022(5) 0.003(5) 0.002(5) C5 0.086(9) 0.097(10) 0.047(7) 0.024(7) 0.029(6) 0.038(8) C3 0.086(8) 0.058(7) 0.051(6) 0.007(5) 0.010(6) 0.009(7) C15 0.087(9) 0.069(8) 0.045(6) 0.000(6) 0.015(6) -0.009(7) C4 0.106(10) 0.072(8) 0.032(5) 0.001(5) 0.008(6) 0.028(7) O1 0.141(10) 0.153(11) 0.083(7) -0.037(7) -0.018(7) -0.002(8) O2 0.061(7) 0.207(15) 0.219(15) 0.044(12) 0.033(8) 0.011(8) _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 N4 2.290(9) . ? Ag1 N8 2.292(8) . ? Ag1 N6 2.324(8) . ? Ag1 N2 2.387(8) . ? N5 N6 1.352(11) . ? N5 C14 1.345(12) . ? N5 C17 1.444(11) . ? C17 N7 1.433(12) . ? C17 C18 1.540(13) . ? C17 H17 0.9800 . ? N8 C13 1.325(13) . ? N8 N7 1.357(11) . ? N6 C16 1.327(11) . ? N2 C6 1.324(12) . ? N2 N1 1.341(11) . ? N7 C11 1.366(12) . ? C7 N3 1.432(12) . ? C7 N1 1.447(11) . ? C7 C8 1.503(12) . ? C7 H7 0.9800 . ? C20 C18 1.370(12) 3_756 ? C20 C19 1.378(13) . ? C20 H20 0.9300 . ? N1 C4 1.359(12) . ? C9 C8 1.384(12) . ? C9 C10 1.391(12) . ? C9 H9 0.9300 . ? C10 C8 1.382(11) 3_656 ? C10 H10 0.9300 . ? N3 N4 1.362(11) . ? N3 C1 1.361(12) . ? C18 C19 1.375(13) . ? C18 C20 1.370(12) 3_756 ? N4 C3 1.329(13) . ? C8 C10 1.382(11) 3_656 ? C19 H19 0.9300 . ? C6 C5 1.369(16) . ? C6 H6 0.9300 . ? C16 C15 1.397(14) . ? C16 H16 0.9300 . ? C2 C1 1.355(15) . ? C2 C3 1.369(16) . ? C2 H2 0.9300 . ? C11 C12 1.357(15) . ? C11 H11 0.9300 . ? C12 C13 1.368(16) . ? C12 H12 0.9300 . ? C14 C15 1.357(14) . ? C14 H14 0.9300 . ? O3 N9 1.238(13) . ? N9 O2 1.183(14) . ? N9 O1 1.221(13) . ? C13 H13 0.9300 . ? C1 H1 0.9300 . ? C5 C4 1.352(16) . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? C15 H15 0.9300 . ? C4 H4 0.9300 . ? 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 N4 Ag1 N8 143.7(3) . . ? N4 Ag1 N6 118.2(3) . . ? N8 Ag1 N6 82.3(3) . . ? N4 Ag1 N2 80.9(3) . . ? N8 Ag1 N2 106.0(3) . . ? N6 Ag1 N2 135.2(3) . . ? N6 N5 C14 112.7(8) . . ? N6 N5 C17 120.7(7) . . ? C14 N5 C17 126.6(9) . . ? N7 C17 N5 112.3(8) . . ? N7 C17 C18 114.7(7) . . ? N5 C17 C18 111.1(7) . . ? N7 C17 H17 106.0 . . ? N5 C17 H17 106.0 . . ? C18 C17 H17 106.0 . . ? C13 N8 N7 104.2(9) . . ? C13 N8 Ag1 133.2(8) . . ? N7 N8 Ag1 121.6(6) . . ? C16 N6 N5 104.5(8) . . ? C16 N6 Ag1 133.0(7) . . ? N5 N6 Ag1 120.9(6) . . ? C6 N2 N1 103.7(9) . . ? C6 N2 Ag1 139.0(8) . . ? N1 N2 Ag1 116.8(5) . . ? N8 N7 C11 110.9(8) . . ? N8 N7 C17 121.3(8) . . ? C11 N7 C17 127.8(9) . . ? N3 C7 N1 112.6(8) . . ? N3 C7 C8 112.3(7) . . ? N1 C7 C8 112.2(7) . . ? N3 C7 H7 106.4 . . ? N1 C7 H7 106.4 . . ? C8 C7 H7 106.4 . . ? C18 C20 C19 120.6(9) 3_756 . ? C18 C20 H20 119.7 3_756 . ? C19 C20 H20 119.7 . . ? N2 N1 C4 111.9(9) . . ? N2 N1 C7 120.3(7) . . ? C4 N1 C7 127.6(10) . . ? C8 C9 C10 121.1(8) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C8 C10 C9 121.1(8) 3_656 . ? C8 C10 H10 119.4 3_656 . ? C9 C10 H10 119.4 . . ? N4 N3 C1 111.1(8) . . ? N4 N3 C7 120.6(8) . . ? C1 N3 C7 128.2(9) . . ? C19 C18 C20 118.9(9) . 3_756 ? C19 C18 C17 117.9(8) . . ? C20 C18 C17 122.8(9) 3_756 . ? C3 N4 N3 105.2(9) . . ? C3 N4 Ag1 136.3(8) . . ? N3 N4 Ag1 117.8(6) . . ? C9 C8 C10 117.7(8) . 3_656 ? C9 C8 C7 121.3(8) . . ? C10 C8 C7 120.6(8) 3_656 . ? C18 C19 C20 120.5(8) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? N2 C6 C5 112.7(11) . . ? N2 C6 H6 123.6 . . ? C5 C6 H6 123.6 . . ? N6 C16 C15 110.5(10) . . ? N6 C16 H16 124.7 . . ? C15 C16 H16 124.7 . . ? C1 C2 C3 107.8(11) . . ? C1 C2 H2 126.1 . . ? C3 C2 H2 126.1 . . ? N7 C11 C12 106.7(10) . . ? N7 C11 H11 126.6 . . ? C12 C11 H11 126.6 . . ? C11 C12 C13 105.6(11) . . ? C11 C12 H12 127.2 . . ? C13 C12 H12 127.2 . . ? N5 C14 C15 105.9(9) . . ? N5 C14 H14 127.0 . . ? C15 C14 H14 127.0 . . ? O2 N9 O1 123.0(14) . . ? O2 N9 O3 119.5(14) . . ? O1 N9 O3 117.5(12) . . ? N8 C13 C12 112.6(11) . . ? N8 C13 H13 123.7 . . ? C12 C13 H13 123.7 . . ? N3 C1 C2 105.5(10) . . ? N3 C1 H1 127.2 . . ? C2 C1 H1 127.2 . . ? C4 C5 C6 105.2(10) . . ? C4 C5 H5 127.4 . . ? C6 C5 H5 127.4 . . ? N4 C3 C2 110.4(11) . . ? N4 C3 H3 124.8 . . ? C2 C3 H3 124.8 . . ? C14 C15 C16 106.3(9) . . ? C14 C15 H15 126.8 . . ? C16 C15 H15 126.8 . . ? C5 C4 N1 106.4(11) . . ? C5 C4 H4 126.8 . . ? N1 C4 H4 126.8 . . ? 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 N6 N5 C17 N7 68.1(11) . . . . ? C14 N5 C17 N7 -114.2(10) . . . . ? N6 N5 C17 C18 -61.9(11) . . . . ? C14 N5 C17 C18 115.9(10) . . . . ? N4 Ag1 N8 C13 -11.6(12) . . . . ? N6 Ag1 N8 C13 -140.1(9) . . . . ? N2 Ag1 N8 C13 85.0(9) . . . . ? N4 Ag1 N8 N7 155.2(6) . . . . ? N6 Ag1 N8 N7 26.6(6) . . . . ? N2 Ag1 N8 N7 -108.3(7) . . . . ? C14 N5 N6 C16 -0.3(11) . . . . ? C17 N5 N6 C16 177.8(9) . . . . ? C14 N5 N6 Ag1 167.3(7) . . . . ? C17 N5 N6 Ag1 -14.7(11) . . . . ? N4 Ag1 N6 C16 -9.2(10) . . . . ? N8 Ag1 N6 C16 139.2(9) . . . . ? N2 Ag1 N6 C16 -115.8(9) . . . . ? N4 Ag1 N6 N5 -172.6(6) . . . . ? N8 Ag1 N6 N5 -24.3(7) . . . . ? N2 Ag1 N6 N5 80.8(8) . . . . ? N4 Ag1 N2 C6 148.2(12) . . . . ? N8 Ag1 N2 C6 4.7(12) . . . . ? N6 Ag1 N2 C6 -90.6(12) . . . . ? N4 Ag1 N2 N1 -41.6(6) . . . . ? N8 Ag1 N2 N1 174.9(6) . . . . ? N6 Ag1 N2 N1 79.6(7) . . . . ? C13 N8 N7 C11 0.0(10) . . . . ? Ag1 N8 N7 C11 -170.1(6) . . . . ? C13 N8 N7 C17 -179.9(8) . . . . ? Ag1 N8 N7 C17 10.1(10) . . . . ? N5 C17 N7 N8 -65.5(10) . . . . ? C18 C17 N7 N8 62.6(10) . . . . ? N5 C17 N7 C11 114.7(10) . . . . ? C18 C17 N7 C11 -117.2(10) . . . . ? C6 N2 N1 C4 2.0(11) . . . . ? Ag1 N2 N1 C4 -171.4(6) . . . . ? C6 N2 N1 C7 178.1(9) . . . . ? Ag1 N2 N1 C7 4.7(11) . . . . ? N3 C7 N1 N2 60.9(11) . . . . ? C8 C7 N1 N2 -66.9(11) . . . . ? N3 C7 N1 C4 -123.7(10) . . . . ? C8 C7 N1 C4 108.5(10) . . . . ? C8 C9 C10 C8 1.6(16) . . . 3_656 ? N1 C7 N3 N4 -72.8(10) . . . . ? C8 C7 N3 N4 55.0(11) . . . . ? N1 C7 N3 C1 111.9(10) . . . . ? C8 C7 N3 C1 -120.4(9) . . . . ? N7 C17 C18 C19 -178.6(8) . . . . ? N5 C17 C18 C19 -49.9(11) . . . . ? N7 C17 C18 C20 8.6(13) . . . 3_756 ? N5 C17 C18 C20 137.3(9) . . . 3_756 ? C1 N3 N4 C3 -0.3(10) . . . . ? C7 N3 N4 C3 -176.4(8) . . . . ? C1 N3 N4 Ag1 -172.5(6) . . . . ? C7 N3 N4 Ag1 11.4(10) . . . . ? N8 Ag1 N4 C3 -31.1(11) . . . . ? N6 Ag1 N4 C3 87.3(10) . . . . ? N2 Ag1 N4 C3 -135.9(10) . . . . ? N8 Ag1 N4 N3 137.9(6) . . . . ? N6 Ag1 N4 N3 -103.7(6) . . . . ? N2 Ag1 N4 N3 33.2(6) . . . . ? C10 C9 C8 C10 -1.5(15) . . . 3_656 ? C10 C9 C8 C7 -174.9(9) . . . . ? N3 C7 C8 C9 -156.5(9) . . . . ? N1 C7 C8 C9 -28.5(12) . . . . ? N3 C7 C8 C10 30.3(12) . . . 3_656 ? N1 C7 C8 C10 158.3(8) . . . 3_656 ? C20 C18 C19 C20 -2.0(16) 3_756 . . . ? C17 C18 C19 C20 -175.1(8) . . . . ? C18 C20 C19 C18 2.0(16) 3_756 . . . ? N1 N2 C6 C5 -1.4(12) . . . . ? Ag1 N2 C6 C5 169.7(8) . . . . ? N5 N6 C16 C15 -0.2(12) . . . . ? Ag1 N6 C16 C15 -165.5(7) . . . . ? N8 N7 C11 C12 0.1(11) . . . . ? C17 N7 C11 C12 179.9(8) . . . . ? N7 C11 C12 C13 -0.1(11) . . . . ? N6 N5 C14 C15 0.6(12) . . . . ? C17 N5 C14 C15 -177.3(9) . . . . ? N7 N8 C13 C12 0.0(11) . . . . ? Ag1 N8 C13 C12 168.3(7) . . . . ? C11 C12 C13 N8 0.1(13) . . . . ? N4 N3 C1 C2 -0.1(11) . . . . ? C7 N3 C1 C2 175.6(9) . . . . ? C3 C2 C1 N3 0.5(11) . . . . ? N2 C6 C5 C4 0.3(14) . . . . ? N3 N4 C3 C2 0.7(11) . . . . ? Ag1 N4 C3 C2 170.6(7) . . . . ? C1 C2 C3 N4 -0.8(13) . . . . ? N5 C14 C15 C16 -0.7(13) . . . . ? N6 C16 C15 C14 0.6(13) . . . . ? C6 C5 C4 N1 0.9(12) . . . . ? N2 N1 C4 C5 -1.9(11) . . . . ? C7 N1 C4 C5 -177.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 1.090 _refine_diff_density_min -0.812 _refine_diff_density_rms 0.112