# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Mir Wais Hosseini' _publ_contact_author_name 'Mir Wais Hosseini' _publ_contact_author_email HOSSEINI@CHIMIE.U-STRASBG.FR _publ_section_title ; Molecular tectonics: an example of design and not serendipity ; # Attachment 'Compound2.cif' data_e1233a _database_code_depnum_ccdc_archive 'CCDC 729992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 N2 O4' _chemical_formula_sum 'C14 H8 N2 O4' _chemical_formula_weight 268.22 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 9.7547(10) _cell_length_b 7.5702(6) _cell_length_c 15.2163(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.189(3) _cell_angle_gamma 90.00 _cell_volume 1089.37(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 899 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 26.70 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9711 _exptl_absorpt_correction_T_max 0.9758 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5993 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2394 _reflns_number_gt 1804 _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, 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^)+(0.0605P)^2^+0.4009P] 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 2394 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 C1 C 0.93480(19) 0.6344(2) 1.09592(13) 0.0207(4) Uani 1 1 d . . . C2 C 1.0167(2) 0.5080(3) 1.15057(15) 0.0255(5) Uani 1 1 d . . . H2 H 1.1001 0.5413 1.1943 0.031 Uiso 1 1 calc R . . C3 C 0.9758(2) 0.3329(3) 1.14072(14) 0.0253(4) Uani 1 1 d . . . H3 H 1.0309 0.2460 1.1786 0.030 Uiso 1 1 calc R . . N1 N 0.86082(16) 0.2846(2) 1.07914(12) 0.0220(4) Uani 1 1 d . . . H1 H 0.8381 0.1719 1.0744 0.026 Uiso 1 1 calc R . . C4 C 0.77616(18) 0.4015(2) 1.02276(13) 0.0195(4) Uani 1 1 d . . . C5 C 0.65111(19) 0.3397(2) 0.95900(13) 0.0187(4) Uani 1 1 d . . . C6 C 0.5038(2) 0.1107(3) 0.90341(14) 0.0239(4) Uani 1 1 d . . . H6 H 0.4802 -0.0110 0.9038 0.029 Uiso 1 1 calc R . . N2 N 0.62001(16) 0.1651(2) 0.96127(12) 0.0225(4) Uani 1 1 d . . . C7 C 0.4130(2) 0.2215(3) 0.84133(14) 0.0231(4) Uani 1 1 d . . . H7 H 0.3315 0.1741 0.8006 0.028 Uiso 1 1 calc R . . C8 C 0.44221(18) 0.3987(2) 0.83962(13) 0.0199(4) Uani 1 1 d . . . C9 C 0.56710(18) 0.4642(2) 0.90034(13) 0.0189(4) Uani 1 1 d . . . C10 C 0.6118(2) 0.6446(3) 0.90464(14) 0.0235(4) Uani 1 1 d . . . H10 H 0.5587 0.7268 0.8625 0.028 Uiso 1 1 calc R . . C11 C 0.7273(2) 0.7018(2) 0.96697(14) 0.0228(4) Uani 1 1 d . . . H11 H 0.7520 0.8234 0.9691 0.027 Uiso 1 1 calc R . . C12 C 0.81281(19) 0.5812(2) 1.02974(13) 0.0201(4) Uani 1 1 d . . . C13 C 0.97605(19) 0.8278(3) 1.10889(13) 0.0225(4) Uani 1 1 d . . . O1 O 1.09767(14) 0.86337(19) 1.09988(11) 0.0334(4) Uani 1 1 d . . . O2 O 0.88830(14) 0.93005(17) 1.12854(11) 0.0298(4) Uani 1 1 d . . . C14 C 0.33853(19) 0.5190(3) 0.77755(14) 0.0227(4) Uani 1 1 d . . . O3 O 0.32796(15) 0.67566(19) 0.79149(11) 0.0331(4) Uani 1 1 d . . . O4 O 0.25931(14) 0.43308(18) 0.70883(10) 0.0305(4) Uani 1 1 d . . . H4 H 0.2022 0.5034 0.6761 0.046 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 C1 0.0214(9) 0.0192(10) 0.0209(10) -0.0024(8) 0.0040(7) 0.0002(7) C2 0.0214(9) 0.0241(11) 0.0277(11) -0.0003(9) -0.0002(8) 0.0024(8) C3 0.0257(9) 0.0218(11) 0.0257(11) 0.0036(9) 0.0012(8) 0.0068(8) N1 0.0243(8) 0.0143(8) 0.0255(10) 0.0008(7) 0.0026(7) 0.0020(6) C4 0.0211(9) 0.0152(10) 0.0223(10) 0.0013(7) 0.0054(7) 0.0031(7) C5 0.0222(8) 0.0134(10) 0.0213(10) -0.0001(8) 0.0069(7) 0.0012(7) C6 0.0262(9) 0.0149(10) 0.0309(11) -0.0003(8) 0.0075(8) -0.0014(7) N2 0.0249(8) 0.0141(8) 0.0275(10) 0.0012(7) 0.0047(7) 0.0008(6) C7 0.0215(9) 0.0203(10) 0.0263(11) -0.0023(8) 0.0035(8) -0.0006(7) C8 0.0214(9) 0.0185(10) 0.0203(10) 0.0009(8) 0.0058(7) 0.0012(7) C9 0.0231(9) 0.0153(10) 0.0189(10) 0.0004(8) 0.0062(7) 0.0021(7) C10 0.0291(10) 0.0152(10) 0.0237(11) 0.0038(8) 0.0018(8) 0.0022(7) C11 0.0277(10) 0.0134(10) 0.0248(11) 0.0003(8) 0.0016(8) -0.0009(7) C12 0.0237(9) 0.0160(10) 0.0207(10) -0.0001(7) 0.0052(7) 0.0011(7) C13 0.0245(9) 0.0203(11) 0.0190(10) -0.0022(8) -0.0018(8) -0.0032(7) O1 0.0262(7) 0.0328(9) 0.0402(10) -0.0112(7) 0.0061(6) -0.0090(6) O2 0.0323(8) 0.0156(8) 0.0416(10) -0.0042(6) 0.0089(7) -0.0004(6) C14 0.0214(9) 0.0201(11) 0.0258(11) 0.0010(8) 0.0043(8) 0.0012(7) O3 0.0343(8) 0.0205(8) 0.0388(10) -0.0029(7) -0.0021(7) 0.0070(6) O4 0.0302(7) 0.0216(8) 0.0311(9) -0.0015(6) -0.0087(6) 0.0045(6) _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 C1 C2 1.386(3) . ? C1 C12 1.416(3) . ? C1 C13 1.518(3) . ? C2 C3 1.382(3) . ? C2 H2 0.9500 . ? C3 N1 1.324(2) . ? C3 H3 0.9500 . ? N1 C4 1.362(2) . ? N1 H1 0.8800 . ? C4 C12 1.404(3) . ? C4 C5 1.438(3) . ? C5 N2 1.358(2) . ? C5 C9 1.413(3) . ? C6 N2 1.319(2) . ? C6 C7 1.404(3) . ? C6 H6 0.9500 . ? C7 C8 1.373(3) . ? C7 H7 0.9500 . ? C8 C9 1.425(3) . ? C8 C14 1.509(3) . ? C9 C10 1.430(3) . ? C10 C11 1.354(3) . ? C10 H10 0.9500 . ? C11 C12 1.432(3) . ? C11 H11 0.9500 . ? C13 O2 1.243(2) . ? C13 O1 1.256(2) . ? C14 O3 1.213(2) . ? C14 O4 1.311(2) . ? O4 H4 0.8400 . ? 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 C2 C1 C12 119.39(17) . . ? C2 C1 C13 119.51(17) . . ? C12 C1 C13 121.10(17) . . ? C3 C2 C1 119.25(18) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? N1 C3 C2 120.90(18) . . ? N1 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 N1 C4 122.96(17) . . ? C3 N1 H1 118.5 . . ? C4 N1 H1 118.5 . . ? N1 C4 C12 118.57(17) . . ? N1 C4 C5 119.79(16) . . ? C12 C4 C5 121.63(17) . . ? N2 C5 C9 124.49(17) . . ? N2 C5 C4 117.21(16) . . ? C9 C5 C4 118.27(16) . . ? N2 C6 C7 124.04(18) . . ? N2 C6 H6 118.0 . . ? C7 C6 H6 118.0 . . ? C6 N2 C5 116.58(16) . . ? C8 C7 C6 119.79(18) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 118.41(17) . . ? C7 C8 C14 119.42(17) . . ? C9 C8 C14 122.10(16) . . ? C5 C9 C8 116.66(16) . . ? C5 C9 C10 119.01(17) . . ? C8 C9 C10 124.32(17) . . ? C11 C10 C9 121.96(18) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C10 C11 C12 120.79(17) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C4 C12 C1 118.91(17) . . ? C4 C12 C11 118.13(17) . . ? C1 C12 C11 122.92(17) . . ? O2 C13 O1 128.11(18) . . ? O2 C13 C1 117.08(17) . . ? O1 C13 C1 114.80(17) . . ? O3 C14 O4 124.47(18) . . ? O3 C14 C8 123.58(18) . . ? O4 C14 C8 111.92(16) . . ? C14 O4 H4 109.5 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.251 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.056 # Attachment '_12+,_22-,_Ag+,_AsF6-_.cif' data_e1574b _database_code_depnum_ccdc_archive 'CCDC 729993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H12 Ag N4 O8, 2(C10 H20 N4), As F6, 2(C H4 O)' _chemical_formula_sum 'C50 H60 Ag As F6 N12 O10' _chemical_formula_weight 1285.89 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' F F 0.0171 0.0103 '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' As As 0.0499 2.0058 '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/m _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.538(2) _cell_length_b 23.019(2) _cell_length_c 5.3934(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.638(5) _cell_angle_gamma 90.00 _cell_volume 2643.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1592 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.40 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9273 _exptl_absorpt_correction_T_max 0.9473 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10656 _diffrn_reflns_av_R_equivalents 0.0767 _diffrn_reflns_av_sigmaI/netI 0.1070 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3089 _reflns_number_gt 2084 _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, 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^)+(0.1044P)^2^+4.3077P] 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 3089 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1335 _refine_ls_R_factor_gt 0.0854 _refine_ls_wR_factor_ref 0.2019 _refine_ls_wR_factor_gt 0.1778 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 C1 C 0.6888(3) 0.1908(3) 0.4309(11) 0.0460(17) Uani 1 1 d . . . N1 N 0.6477(3) 0.1905(3) 0.2244(10) 0.0504(15) Uani 1 1 d . . . H1 H 0.6373 0.2237 0.1483 0.060 Uiso 1 1 calc R . . C2 C 0.6189(4) 0.1374(4) 0.1175(14) 0.066(2) Uani 1 1 d . . . H2A H 0.6089 0.1413 -0.0670 0.080 Uiso 1 1 calc R . . H2B H 0.5793 0.1301 0.1845 0.080 Uiso 1 1 calc R . . C3 C 0.6637(4) 0.0866(4) 0.1825(17) 0.078(3) Uani 1 1 d . . . H3A H 0.6423 0.0497 0.1278 0.094 Uiso 1 1 calc R . . H3B H 0.7006 0.0909 0.0946 0.094 Uiso 1 1 calc R . . C4 C 0.6848(4) 0.0855(4) 0.4644(17) 0.082(3) Uani 1 1 d . . . H4A H 0.6495 0.0730 0.5500 0.098 Uiso 1 1 calc R . . H4B H 0.7194 0.0572 0.5051 0.098 Uiso 1 1 calc R . . N2 N 0.7060(3) 0.1428(3) 0.5527(11) 0.0594(17) Uani 1 1 d . . . H2 H 0.7317 0.1454 0.6954 0.071 Uiso 1 1 calc R . . C5 C 0.7169(3) 0.2466(3) 0.5275(11) 0.0470(17) Uani 1 1 d . . . H5A H 0.7170 0.2485 0.7110 0.056 Uiso 1 1 calc R . . H5B H 0.6908 0.2791 0.4495 0.056 Uiso 1 1 calc R . . Ag1 Ag 0.0000 0.0000 0.0000 0.0278(3) Uani 1 4 d S . . N3 N 0.05661(19) 0.0587(2) 0.3148(7) 0.0291(11) Uani 1 1 d . . . C6 C 0.0548(3) 0.1161(3) 0.3182(10) 0.0389(15) Uani 1 1 d . . . H6 H 0.0312 0.1355 0.1796 0.047 Uiso 1 1 calc R . . C7 C 0.0854(3) 0.1494(3) 0.5117(11) 0.0422(15) Uani 1 1 d . . . H7 H 0.0817 0.1905 0.5051 0.051 Uiso 1 1 calc R . . C8 C 0.1209(3) 0.1234(3) 0.7135(10) 0.0387(15) Uani 1 1 d . . . C9 C 0.1244(2) 0.0619(3) 0.7165(9) 0.0342(14) Uani 1 1 d . . . C10 C 0.0901(2) 0.0315(2) 0.5141(8) 0.0269(12) Uani 1 1 d . . . C11 C 0.1589(3) 0.0289(3) 0.9176(9) 0.0423(17) Uani 1 1 d . . . H11 H 0.1823 0.0490 1.0547 0.051 Uiso 1 1 calc R . . C12 C 0.1553(4) 0.1619(4) 0.9196(12) 0.056(2) Uani 1 1 d . . . O1 O 0.2085(2) 0.1477(3) 1.0155(10) 0.0805(19) Uani 1 1 d . . . O2 O 0.1257(3) 0.2064(2) 0.9674(9) 0.0631(15) Uani 1 1 d . . . As1 As 0.5000 0.0000 0.5000 0.0993(9) Uani 1 4 d S . . F1 F 0.5458(4) 0.0000 0.2762(16) 0.159(5) Uani 1 2 d S . . F2 F 0.4370(5) 0.0000 0.3023(19) 0.233(9) Uani 1 2 d S . . F3 F 0.5000 0.0716(8) 0.5000 0.233(9) Uani 1 2 d S . . O3 O 0.9959(7) 0.2556(6) 0.151(3) 0.136(8) Uani 0.50 1 d P . . C16 C 0.9762(11) 0.2925(12) 0.346(5) 0.141(13) Uani 0.50 1 d P . . 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 C1 0.035(4) 0.067(5) 0.037(3) 0.017(3) 0.009(3) 0.015(3) N1 0.046(3) 0.058(4) 0.044(3) 0.019(3) -0.003(2) 0.011(3) C2 0.064(5) 0.071(6) 0.059(4) 0.017(4) -0.010(4) 0.012(4) C3 0.083(6) 0.061(6) 0.086(6) 0.012(5) -0.004(5) 0.007(5) C4 0.076(6) 0.071(6) 0.090(6) 0.038(5) -0.011(5) 0.008(5) N2 0.046(3) 0.075(5) 0.054(3) 0.026(3) -0.004(3) 0.012(3) C5 0.040(4) 0.067(5) 0.036(3) 0.008(3) 0.010(3) 0.015(3) Ag1 0.0272(5) 0.0355(6) 0.0190(4) 0.000 -0.0018(3) 0.000 N3 0.025(2) 0.041(3) 0.019(2) 0.0016(19) -0.0036(17) -0.008(2) C6 0.041(4) 0.048(4) 0.026(3) 0.005(3) 0.000(2) -0.010(3) C7 0.044(4) 0.045(4) 0.038(3) -0.004(3) 0.009(3) -0.017(3) C8 0.031(3) 0.062(4) 0.025(3) -0.013(3) 0.009(2) -0.019(3) C9 0.022(3) 0.059(4) 0.023(3) -0.007(3) 0.006(2) -0.010(3) C10 0.019(3) 0.046(3) 0.016(2) -0.003(2) 0.0028(19) -0.002(2) C11 0.023(3) 0.084(5) 0.017(2) -0.004(2) -0.003(2) -0.007(3) C12 0.052(5) 0.088(6) 0.031(3) -0.018(4) 0.015(3) -0.040(4) O1 0.050(3) 0.129(5) 0.058(3) -0.034(3) -0.009(3) -0.034(3) O2 0.073(4) 0.069(4) 0.048(3) -0.026(3) 0.013(2) -0.031(3) As1 0.0320(10) 0.210(3) 0.0579(11) 0.000 0.0138(8) 0.000 F1 0.068(6) 0.325(16) 0.092(6) 0.000 0.042(5) 0.000 F2 0.095(8) 0.52(3) 0.081(7) 0.000 0.015(6) 0.000 F3 0.095(8) 0.52(3) 0.081(7) 0.000 0.015(6) 0.000 O3 0.062(8) 0.089(10) 0.23(2) 0.086(11) -0.055(14) -0.029(8) C16 0.088(18) 0.13(2) 0.22(3) 0.13(2) 0.078(18) 0.072(15) _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 C1 N2 1.309(8) . ? C1 N1 1.314(8) . ? C1 C5 1.481(10) . ? N1 C2 1.451(10) . ? N1 H1 0.8800 . ? C2 C3 1.521(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(12) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.452(11) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 C5 1.509(12) 7_656 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? Ag1 N3 2.360(4) 5 ? Ag1 N3 2.360(4) 6 ? Ag1 N3 2.360(4) 2 ? Ag1 N3 2.360(4) . ? N3 C6 1.324(7) . ? N3 C10 1.353(6) . ? C6 C7 1.379(8) . ? C6 H6 0.9500 . ? C7 C8 1.371(8) . ? C7 H7 0.9500 . ? C8 C9 1.417(9) . ? C8 C12 1.525(8) . ? C9 C10 1.409(7) . ? C9 C11 1.436(8) . ? C10 C10 1.451(11) 6 ? C11 C11 1.332(13) 6 ? C11 H11 0.9500 . ? C12 O1 1.228(9) . ? C12 O2 1.252(10) . ? As1 F2 1.594(11) . ? As1 F2 1.595(11) 5_656 ? As1 F3 1.648(18) . ? As1 F3 1.648(18) 5_656 ? As1 F1 1.670(7) 5_656 ? As1 F1 1.670(7) . ? O3 C16 1.46(3) . ? 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 C1 N1 121.7(7) . . ? N2 C1 C5 119.0(6) . . ? N1 C1 C5 119.3(6) . . ? C1 N1 C2 122.3(6) . . ? C1 N1 H1 118.9 . . ? C2 N1 H1 118.9 . . ? N1 C2 C3 109.7(6) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 109.2(8) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? N2 C4 C3 110.1(7) . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C1 N2 C4 123.4(6) . . ? C1 N2 H2 118.3 . . ? C4 N2 H2 118.3 . . ? C1 C5 C5 111.6(7) . 7_656 ? C1 C5 H5A 109.3 . . ? C5 C5 H5A 109.3 7_656 . ? C1 C5 H5B 109.3 . . ? C5 C5 H5B 109.3 7_656 . ? H5A C5 H5B 108.0 . . ? N3 Ag1 N3 110.2(2) 5 6 ? N3 Ag1 N3 69.8(2) 5 2 ? N3 Ag1 N3 180.0(3) 6 2 ? N3 Ag1 N3 180.0 5 . ? N3 Ag1 N3 69.8(2) 6 . ? N3 Ag1 N3 110.2(2) 2 . ? C6 N3 C10 117.6(4) . . ? C6 N3 Ag1 124.7(3) . . ? C10 N3 Ag1 117.6(4) . . ? N3 C6 C7 123.6(5) . . ? N3 C6 H6 118.2 . . ? C7 C6 H6 118.2 . . ? C8 C7 C6 120.3(6) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 117.9(5) . . ? C7 C8 C12 118.5(6) . . ? C9 C8 C12 123.6(6) . . ? C10 C9 C8 117.8(5) . . ? C10 C9 C11 118.3(6) . . ? C8 C9 C11 123.9(5) . . ? N3 C10 C9 122.7(5) . . ? N3 C10 C10 117.5(3) . 6 ? C9 C10 C10 119.8(3) . 6 ? C11 C11 C9 121.9(3) 6 . ? C11 C11 H11 119.0 6 . ? C9 C11 H11 119.0 . . ? O1 C12 O2 127.1(6) . . ? O1 C12 C8 118.1(8) . . ? O2 C12 C8 114.7(7) . . ? C16 O3 O3 142.0(11) . 2_755 ? O3 C16 C16 118.2(16) . 2_756 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.809 _refine_diff_density_min -1.839 _refine_diff_density_rms 0.120 # Attachment '_12+,_22-,_Ag+,_PF6-_.cif' data_e1348a _database_code_depnum_ccdc_archive 'CCDC 729994' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H12 Ag N4 O8, 2(C10 H20 N4), F6 P, 2(CH3 OH)' _chemical_formula_sum 'C50 H60 Ag F6 N12 O10 P' _chemical_formula_weight 1241.94 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' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 '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/m _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.4159(17) _cell_length_b 23.109(3) _cell_length_c 5.4593(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.117(6) _cell_angle_gamma 90.00 _cell_volume 2667.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1359 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.94 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.499 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9755 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10864 _diffrn_reflns_av_R_equivalents 0.1427 _diffrn_reflns_av_sigmaI/netI 0.1637 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3089 _reflns_number_gt 1865 _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, 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^)+(0.1408P)^2^+16.9019P] 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 3089 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1840 _refine_ls_R_factor_gt 0.1026 _refine_ls_wR_factor_ref 0.3095 _refine_ls_wR_factor_gt 0.2352 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 C1 C 0.6874(4) 0.1910(4) 0.4288(17) 0.045(2) Uani 1 1 d . . . N1 N 0.6469(4) 0.1903(3) 0.2230(14) 0.0458(19) Uani 1 1 d . . . H1 H 0.6364 0.2233 0.1470 0.055 Uiso 1 1 calc R . . C2 C 0.6186(5) 0.1373(4) 0.115(2) 0.060(3) Uani 1 1 d . . . H2A H 0.6104 0.1410 -0.0681 0.072 Uiso 1 1 calc R . . H2B H 0.5776 0.1307 0.1727 0.072 Uiso 1 1 calc R . . C3 C 0.6607(6) 0.0870(5) 0.185(2) 0.073(3) Uani 1 1 d . . . H3A H 0.6979 0.0896 0.0985 0.088 Uiso 1 1 calc R . . H3B H 0.6378 0.0508 0.1316 0.088 Uiso 1 1 calc R . . C4 C 0.6828(6) 0.0853(5) 0.464(2) 0.072(3) Uani 1 1 d . . . H4A H 0.6475 0.0730 0.5493 0.086 Uiso 1 1 calc R . . H4B H 0.7176 0.0569 0.5035 0.086 Uiso 1 1 calc R . . N2 N 0.7049(4) 0.1429(3) 0.5516(14) 0.053(2) Uani 1 1 d . . . H2 H 0.7311 0.1455 0.6926 0.063 Uiso 1 1 calc R . . C5 C 0.7167(4) 0.2464(4) 0.5282(16) 0.042(2) Uani 1 1 d . . . H5A H 0.7177 0.2475 0.7101 0.050 Uiso 1 1 calc R . . H5B H 0.6903 0.2792 0.4547 0.050 Uiso 1 1 calc R . . Ag1 Ag 0.0000 0.0000 0.0000 0.0389(5) Uani 1 4 d S . . N3 N 0.0567(3) 0.0591(4) 0.3170(11) 0.0411(18) Uani 1 1 d . . . C6 C 0.0550(4) 0.1160(4) 0.3171(15) 0.042(2) Uani 1 1 d . . . H6 H 0.0315 0.1352 0.1785 0.051 Uiso 1 1 calc R . . C7 C 0.0860(4) 0.1490(4) 0.5113(15) 0.040(2) Uani 1 1 d . . . H7 H 0.0823 0.1899 0.5057 0.048 Uiso 1 1 calc R . . C8 C 0.1221(4) 0.1231(4) 0.7110(13) 0.038(2) Uani 1 1 d . . . C9 C 0.1249(3) 0.0616(4) 0.7167(12) 0.0310(18) Uani 1 1 d . . . C10 C 0.0905(3) 0.0313(4) 0.5124(13) 0.0332(18) Uani 1 1 d . . . C11 C 0.1589(4) 0.0291(4) 0.9184(13) 0.039(2) Uani 1 1 d . . . H11 H 0.1821 0.0491 1.0553 0.046 Uiso 1 1 calc R . . C12 C 0.1563(4) 0.1611(4) 0.9178(15) 0.041(2) Uani 1 1 d . . . O1 O 0.2100(3) 0.1467(3) 1.0152(12) 0.0615(19) Uani 1 1 d . . . O2 O 0.1273(3) 0.2053(3) 0.9662(12) 0.0550(18) Uani 1 1 d . . . P1 P 0.5000 1.0000 0.5000 0.086(2) Uani 1 4 d S . . F1 F 0.5465(6) 1.0000 0.310(3) 0.165(7) Uani 1 2 d S . . F2 F 0.4416(9) 1.0000 0.314(3) 0.165(7) Uani 1 2 d S . . F3 F 0.5000 0.9383(10) 0.5000 0.165(7) Uani 1 2 d S . . O3 O 0.9911(10) 0.2582(8) 0.161(5) 0.135(13) Uani 0.50 1 d P . . C16 C 0.981(2) 0.299(2) 0.362(10) 0.23(4) Uani 0.50 1 d P . . 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 C1 0.035(5) 0.052(6) 0.044(5) 0.002(4) -0.003(4) 0.006(4) N1 0.050(4) 0.041(4) 0.040(4) 0.004(3) -0.010(3) -0.005(4) C2 0.067(7) 0.043(6) 0.058(6) 0.007(5) -0.025(5) -0.016(5) C3 0.089(9) 0.048(7) 0.073(8) 0.000(6) -0.017(6) -0.012(6) C4 0.084(8) 0.058(7) 0.062(7) 0.008(6) -0.027(6) -0.013(6) N2 0.055(5) 0.050(5) 0.046(4) 0.009(4) -0.013(4) -0.013(4) C5 0.047(5) 0.038(5) 0.036(4) -0.009(4) -0.004(4) -0.005(4) Ag1 0.0324(7) 0.0633(10) 0.0162(6) 0.000 -0.0112(4) 0.000 N3 0.034(4) 0.066(6) 0.019(3) 0.008(3) -0.009(3) 0.003(3) C6 0.038(5) 0.053(6) 0.033(4) 0.012(4) -0.004(3) -0.002(4) C7 0.041(5) 0.034(5) 0.040(4) 0.008(4) -0.007(4) -0.004(4) C8 0.034(4) 0.056(6) 0.022(4) 0.006(4) -0.006(3) -0.001(4) C9 0.026(4) 0.045(5) 0.019(3) 0.008(3) -0.005(3) -0.006(3) C10 0.029(4) 0.049(5) 0.019(3) 0.001(3) -0.004(3) 0.000(3) C11 0.039(4) 0.056(5) 0.017(3) -0.001(3) -0.007(3) -0.001(4) C12 0.052(6) 0.035(5) 0.034(4) 0.001(4) -0.002(4) -0.010(4) O1 0.045(4) 0.076(5) 0.053(4) -0.012(4) -0.022(3) -0.006(3) O2 0.063(4) 0.052(4) 0.045(4) -0.004(3) -0.004(3) -0.014(4) P1 0.047(4) 0.135(8) 0.077(5) 0.000 0.013(3) 0.000 F1 0.092(9) 0.31(2) 0.110(11) 0.000 0.059(9) 0.000 F2 0.092(9) 0.31(2) 0.110(11) 0.000 0.059(9) 0.000 F3 0.092(9) 0.31(2) 0.110(11) 0.000 0.059(9) 0.000 O3 0.094(16) 0.069(12) 0.20(3) 0.037(13) -0.10(2) -0.031(11) C16 0.15(5) 0.29(6) 0.29(8) 0.25(6) 0.11(5) 0.08(5) _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 C1 N1 1.305(11) . ? C1 N2 1.322(12) . ? C1 C5 1.490(12) . ? N1 C2 1.452(11) . ? N1 H1 0.8800 . ? C2 C3 1.482(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.466(13) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 C5 1.517(18) 7_656 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? Ag1 N3 2.380(7) . ? Ag1 N3 2.380(7) 5 ? Ag1 N3 2.380(7) 6 ? Ag1 N3 2.380(7) 2 ? N3 C6 1.315(11) . ? N3 C10 1.353(9) . ? C6 C7 1.388(12) . ? C6 H6 0.9500 . ? C7 C8 1.369(11) . ? C7 H7 0.9500 . ? C8 C9 1.424(12) . ? C8 C12 1.523(11) . ? C9 C10 1.420(10) . ? C9 C11 1.433(10) . ? C10 C10 1.446(17) 6 ? C11 C11 1.344(17) 6 ? C11 H11 0.9500 . ? C12 O1 1.234(11) . ? C12 O2 1.246(11) . ? P1 F3 1.42(2) . ? P1 F3 1.42(2) 5_676 ? P1 F2 1.481(18) 5_676 ? P1 F2 1.481(18) . ? P1 F1 1.550(12) . ? P1 F1 1.550(12) 5_676 ? O3 C16 1.49(7) . ? C16 C16 1.60(11) 2_756 ? 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 C1 N2 121.5(9) . . ? N1 C1 C5 120.5(8) . . ? N2 C1 C5 118.0(8) . . ? C1 N1 C2 122.5(8) . . ? C1 N1 H1 118.7 . . ? C2 N1 H1 118.7 . . ? N1 C2 C3 111.0(8) . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 111.0(11) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N2 C4 C3 109.5(9) . . ? N2 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? N2 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C1 N2 C4 123.2(8) . . ? C1 N2 H2 118.4 . . ? C4 N2 H2 118.4 . . ? C1 C5 C5 112.1(9) . 7_656 ? C1 C5 H5A 109.2 . . ? C5 C5 H5A 109.2 7_656 . ? C1 C5 H5B 109.2 . . ? C5 C5 H5B 109.2 7_656 . ? H5A C5 H5B 107.9 . . ? N3 Ag1 N3 180.0 . 5 ? N3 Ag1 N3 70.0(4) . 6 ? N3 Ag1 N3 110.0(4) 5 6 ? N3 Ag1 N3 110.0(4) . 2 ? N3 Ag1 N3 70.0(4) 5 2 ? N3 Ag1 N3 180.0(4) 6 2 ? C6 N3 C10 119.0(7) . . ? C6 N3 Ag1 124.2(5) . . ? C10 N3 Ag1 116.7(6) . . ? N3 C6 C7 122.7(8) . . ? N3 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C8 C7 C6 120.6(8) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 118.0(7) . . ? C7 C8 C12 118.9(8) . . ? C9 C8 C12 123.1(7) . . ? C10 C9 C8 117.4(7) . . ? C10 C9 C11 118.9(7) . . ? C8 C9 C11 123.7(7) . . ? N3 C10 C9 122.1(8) . . ? N3 C10 C10 118.3(5) . 6 ? C9 C10 C10 119.5(5) . 6 ? C11 C11 C9 121.6(5) 6 . ? C11 C11 H11 119.2 6 . ? C9 C11 H11 119.2 . . ? O1 C12 O2 126.2(8) . . ? O1 C12 C8 118.1(8) . . ? O2 C12 C8 115.6(8) . . ? F3 P1 F3 180.000(11) . 5_676 ? F3 P1 F2 90.000(10) . 5_676 ? F3 P1 F2 90.000(11) 5_676 5_676 ? F3 P1 F2 90.000(11) . . ? F3 P1 F2 90.000(10) 5_676 . ? F2 P1 F2 180.000(8) 5_676 . ? F3 P1 F1 90.000(8) . . ? F3 P1 F1 90.000(10) 5_676 . ? F2 P1 F1 84.1(9) 5_676 . ? F2 P1 F1 95.9(9) . . ? F3 P1 F1 90.000(10) . 5_676 ? F3 P1 F1 90.000(8) 5_676 5_676 ? F2 P1 F1 95.9(9) 5_676 5_676 ? F2 P1 F1 84.1(9) . 5_676 ? F1 P1 F1 179.998(8) . 5_676 ? O3 C16 C16 125(3) . 2_756 ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.977 _refine_diff_density_min -0.823 _refine_diff_density_rms 0.141 # Attachment '_12+,_22-,_Ag+,_SbF6-__.cif' data_e1149a _database_code_depnum_ccdc_archive 'CCDC 729995' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H12 AG N4 O8, 2(C10 H20 N4), F6 Sb, 2(CH3OH)' _chemical_formula_sum 'C50 H60 Ag F6 N12 O10 Sb' _chemical_formula_weight 1332.72 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' F F 0.0171 0.0103 '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' Sb Sb -0.5866 1.5461 '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/m _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.8809(18) _cell_length_b 23.0194(18) _cell_length_c 5.3675(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.574(4) _cell_angle_gamma 90.00 _cell_volume 2673.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1992 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 22.64 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9357 _exptl_absorpt_correction_T_max 0.9535 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12061 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3122 _reflns_number_gt 2236 _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, 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^)+(0.1194P)^2^+38.3693P] 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 3122 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1222 _refine_ls_R_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.2547 _refine_ls_wR_factor_gt 0.2115 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.098 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 C1 C 0.6900(4) 0.1896(6) 0.427(2) 0.066(4) Uani 1 1 d . . . N1 N 0.6487(4) 0.1905(5) 0.2256(19) 0.065(3) Uani 1 1 d . . . H1 H 0.6364 0.2241 0.1581 0.078 Uiso 1 1 calc R . . C2 C 0.6224(6) 0.1375(6) 0.110(3) 0.080(4) Uani 1 1 d . . . H2A H 0.6144 0.1423 -0.0753 0.095 Uiso 1 1 calc R . . H2B H 0.5824 0.1294 0.1689 0.095 Uiso 1 1 calc R . . C3 C 0.6652(7) 0.0879(7) 0.176(3) 0.095(5) Uani 1 1 d . . . H3A H 0.7016 0.0924 0.0876 0.114 Uiso 1 1 calc R . . H3B H 0.6441 0.0513 0.1177 0.114 Uiso 1 1 calc R . . C4 C 0.6869(6) 0.0843(7) 0.458(3) 0.090(5) Uani 1 1 d . . . H4A H 0.6526 0.0707 0.5447 0.109 Uiso 1 1 calc R . . H4B H 0.7213 0.0561 0.4930 0.109 Uiso 1 1 calc R . . N2 N 0.7077(5) 0.1421(6) 0.554(2) 0.089(4) Uani 1 1 d . . . H2 H 0.7324 0.1449 0.6992 0.107 Uiso 1 1 calc R . . C5 C 0.7177(4) 0.2463(6) 0.529(2) 0.066(4) Uani 1 1 d . . . H5A H 0.7184 0.2473 0.7141 0.079 Uiso 1 1 calc R . . H5B H 0.6916 0.2788 0.4547 0.079 Uiso 1 1 calc R . . Ag1 Ag 0.0000 0.0000 0.0000 0.0277(3) Uani 1 4 d S . . N3 N 0.0565(3) 0.0586(3) 0.3148(12) 0.0352(16) Uani 1 1 d . . . C6 C 0.0549(4) 0.1163(4) 0.3196(19) 0.044(2) Uani 1 1 d . . . H6 H 0.0313 0.1356 0.1809 0.052 Uiso 1 1 calc R . . C7 C 0.0853(4) 0.1505(5) 0.513(2) 0.053(3) Uani 1 1 d . . . H7 H 0.0818 0.1916 0.5058 0.064 Uiso 1 1 calc R . . C8 C 0.1207(4) 0.1240(5) 0.7176(19) 0.050(3) Uani 1 1 d . . . C9 C 0.1244(4) 0.0615(5) 0.7167(15) 0.043(2) Uani 1 1 d . . . C10 C 0.0900(3) 0.0311(4) 0.5136(14) 0.0321(18) Uani 1 1 d . . . C11 C 0.1582(4) 0.0295(5) 0.9203(16) 0.057(3) Uani 1 1 d . . . H11 H 0.1810 0.0498 1.0578 0.068 Uiso 1 1 calc R . . C12 C 0.1553(5) 0.1623(6) 0.921(2) 0.064(4) Uani 1 1 d . . . O1 O 0.2073(4) 0.1483(5) 1.014(2) 0.102(4) Uani 1 1 d . . . O2 O 0.1266(3) 0.2070(4) 0.9677(16) 0.071(3) Uani 1 1 d . . . Sb1 Sb 0.5000 1.0000 0.5000 0.0501(4) Uani 1 4 d S . . F1 F 0.5476(7) 1.0000 0.245(3) 0.140(7) Uani 1 2 d S . . F2 F 0.4272(8) 1.0000 0.293(3) 0.206(12) Uani 1 2 d S . . F3 F 0.5000 0.9218(6) 0.5000 0.210(8) Uani 1 2 d S . . O3 O 0.9937(9) 0.2525(7) 0.144(4) 0.096(8) Uani 0.50 1 d P . . C16 C 0.9829(16) 0.2976(15) 0.371(7) 0.103(11) Uani 0.50 1 d P . . 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 C1 0.019(4) 0.101(9) 0.077(8) 0.052(7) -0.001(4) -0.014(5) N1 0.034(4) 0.083(7) 0.072(6) 0.042(6) -0.015(4) -0.015(4) C2 0.054(7) 0.091(10) 0.087(9) 0.053(8) -0.013(6) -0.017(7) C3 0.057(8) 0.096(11) 0.125(13) 0.054(10) -0.011(8) -0.019(7) C4 0.059(8) 0.087(10) 0.116(12) 0.058(9) -0.018(8) -0.023(7) N2 0.053(6) 0.113(9) 0.091(8) 0.070(7) -0.025(5) -0.031(6) C5 0.032(5) 0.090(9) 0.072(8) 0.044(7) -0.003(5) -0.017(5) Ag1 0.0273(6) 0.0369(7) 0.0158(5) 0.000 -0.0074(4) 0.000 N3 0.029(3) 0.049(4) 0.024(3) -0.004(3) -0.007(3) -0.001(3) C6 0.029(4) 0.052(6) 0.047(5) -0.008(4) -0.006(4) -0.003(4) C7 0.027(4) 0.056(6) 0.072(7) -0.029(6) -0.008(4) 0.005(4) C8 0.027(4) 0.077(8) 0.045(5) -0.034(5) 0.003(4) -0.007(4) C9 0.020(3) 0.089(8) 0.019(4) -0.019(4) -0.004(3) -0.004(4) C10 0.018(3) 0.058(5) 0.019(3) -0.008(3) -0.001(3) 0.000(3) C11 0.026(4) 0.121(10) 0.020(4) -0.006(4) -0.005(3) 0.006(5) C12 0.035(5) 0.100(9) 0.055(7) -0.050(7) -0.003(5) -0.002(6) O1 0.035(4) 0.147(10) 0.113(8) -0.084(7) -0.027(5) 0.015(5) O2 0.041(4) 0.094(6) 0.074(6) -0.053(5) -0.001(4) -0.007(4) Sb1 0.0314(7) 0.0688(10) 0.0514(8) 0.000 0.0104(6) 0.000 F1 0.092(10) 0.25(2) 0.085(10) 0.000 0.047(8) 0.000 F2 0.086(11) 0.44(4) 0.084(11) 0.000 -0.014(9) 0.000 F3 0.36(3) 0.078(8) 0.222(13) 0.000 0.137(15) 0.000 O3 0.062(11) 0.056(10) 0.151(19) 0.021(11) -0.043(14) -0.014(9) C16 0.08(2) 0.10(2) 0.13(3) 0.04(2) 0.04(2) 0.040(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 C1 N1 1.301(13) . ? C1 N2 1.319(15) . ? C1 C5 1.506(19) . ? N1 C2 1.449(17) . ? N1 H1 0.8800 . ? C2 C3 1.49(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.52(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.47(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 C5 1.50(2) 7_656 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? Ag1 N3 2.363(7) . ? Ag1 N3 2.363(7) 5 ? Ag1 N3 2.363(7) 6 ? Ag1 N3 2.363(7) 2 ? N3 C6 1.329(12) . ? N3 C10 1.358(10) . ? C6 C7 1.392(12) . ? C6 H6 0.9500 . ? C7 C8 1.386(15) . ? C7 H7 0.9500 . ? C8 C9 1.440(16) . ? C8 C12 1.514(12) . ? C9 C10 1.415(10) . ? C9 C11 1.429(13) . ? C10 C10 1.430(18) 6 ? C11 C11 1.36(2) 6 ? C11 H11 0.9500 . ? C12 O1 1.216(13) . ? C12 O2 1.250(14) . ? Sb1 F2 1.801(16) 5_676 ? Sb1 F2 1.801(16) . ? Sb1 F3 1.800(13) 5_676 ? Sb1 F3 1.800(13) . ? Sb1 F1 1.839(13) 5_676 ? Sb1 F1 1.839(13) . ? O3 O3 1.61(5) 2_755 ? O3 C16 1.64(4) . ? C16 C16 1.48(7) 2_756 ? 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 C1 N2 123.9(13) . . ? N1 C1 C5 118.8(10) . . ? N2 C1 C5 117.2(10) . . ? C1 N1 C2 121.7(11) . . ? C1 N1 H1 119.4 . . ? C2 N1 H1 119.0 . . ? N1 C2 C3 110.4(10) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 111.8(16) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C3 109.4(11) . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4B 109.9 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.2 . . ? C1 N2 C4 121.0(11) . . ? C1 N2 H2 119.6 . . ? C4 N2 H2 119.4 . . ? C1 C5 C5 111.2(15) . 7_656 ? C1 C5 H5A 109.4 . . ? C5 C5 H5A 109.5 7_656 . ? C1 C5 H5B 109.4 . . ? C5 C5 H5B 109.3 7_656 . ? H5A C5 H5B 108.0 . . ? N3 Ag1 N3 180.0(5) . 5 ? N3 Ag1 N3 69.7(4) . 6 ? N3 Ag1 N3 110.3(4) 5 6 ? N3 Ag1 N3 110.3(4) . 2 ? N3 Ag1 N3 69.7(4) 5 2 ? N3 Ag1 N3 180.0(4) 6 2 ? C6 N3 C10 117.7(7) . . ? C6 N3 Ag1 124.9(6) . . ? C10 N3 Ag1 117.3(6) . . ? N3 C6 C7 124.6(9) . . ? N3 C6 H6 117.7 . . ? C7 C6 H6 117.7 . . ? C8 C7 C6 119.4(10) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 117.6(8) . . ? C7 C8 C12 118.3(11) . . ? C9 C8 C12 124.1(10) . . ? C10 C9 C11 119.2(10) . . ? C10 C9 C8 118.2(8) . . ? C11 C9 C8 122.4(8) . . ? N3 C10 C9 122.4(9) . . ? N3 C10 C10 117.9(5) . 6 ? C9 C10 C10 119.7(6) . 6 ? C11 C11 C9 121.1(6) 6 . ? C11 C11 H11 119.5 6 . ? C9 C11 H11 119.5 . . ? O1 C12 O2 127.0(10) . . ? O1 C12 C8 118.5(10) . . ? O2 C12 C8 114.4(9) . . ? F3 Sb1 F3 180.000(2) 5_676 . ? F2 Sb1 F1 95.1(8) 5_676 5_676 ? F2 Sb1 F1 84.9(8) . 5_676 ? F3 Sb1 F1 90.000(4) 5_676 5_676 ? F3 Sb1 F1 90.000(7) . 5_676 ? F2 Sb1 F1 84.9(8) 5_676 . ? F2 Sb1 F1 95.1(8) . . ? F3 Sb1 F1 90.000(7) 5_676 . ? F3 Sb1 F1 90.000(5) . . ? F1 Sb1 F1 180.000(6) 5_676 . ? O3 O3 C16 140.8(13) 2_755 . ? C16 C16 O3 126(2) 2_756 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.724 _refine_diff_density_min -1.318 _refine_diff_density_rms 0.188 # Attachment '_12+,_22-__complex.cif' data_e1618a _database_code_depnum_ccdc_archive 'CCDC 729996' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 N4, C14 H6 N2 O4, 2(C H Cl3)' _chemical_formula_sum 'C26 H28 Cl6 N6 O4' _chemical_formula_weight 701.24 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.0015(12) _cell_length_b 14.7201(17) _cell_length_c 21.396(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3150.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2416 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.44 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9712 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19376 _diffrn_reflns_av_R_equivalents 0.0893 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.35 _reflns_number_total 6424 _reflns_number_gt 5567 _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, 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^)+(0.0000P)^2^+9.2096P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(11) _refine_ls_number_reflns 6424 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1549 _refine_ls_goodness_of_fit_ref 1.241 _refine_ls_restrained_S_all 1.241 _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 C1 C 0.2559(5) 1.1026(4) 0.8436(2) 0.0279(11) Uani 1 1 d . . . N1 N 0.3443(5) 1.1479(3) 0.8765(2) 0.0296(10) Uani 1 1 d . . . H1 H 0.4215 1.1222 0.8852 0.035 Uiso 1 1 calc R . . C2 C 0.3179(6) 1.2397(4) 0.8990(3) 0.0370(13) Uani 1 1 d . . . H2A H 0.3505 1.2845 0.8680 0.044 Uiso 1 1 calc R . . H2B H 0.3663 1.2500 0.9387 0.044 Uiso 1 1 calc R . . C3 C 0.1695(6) 1.2524(4) 0.9092(3) 0.0349(12) Uani 1 1 d . . . H3A H 0.1506 1.3167 0.9195 0.042 Uiso 1 1 calc R . . H3B H 0.1395 1.2142 0.9446 0.042 Uiso 1 1 calc R . . C4 C 0.0943(6) 1.2258(4) 0.8505(3) 0.0373(14) Uani 1 1 d . . . H4A H -0.0028 1.2242 0.8592 0.045 Uiso 1 1 calc R . . H4B H 0.1106 1.2714 0.8173 0.045 Uiso 1 1 calc R . . N2 N 0.1387(5) 1.1364(3) 0.8291(2) 0.0304(10) Uani 1 1 d . . . H2 H 0.0845 1.1040 0.8056 0.037 Uiso 1 1 calc R . . C5 C 0.2888(6) 1.0090(3) 0.8230(2) 0.0285(11) Uani 1 1 d . . . H5A H 0.3857 1.0050 0.8140 0.034 Uiso 1 1 calc R . . H5B H 0.2398 0.9952 0.7840 0.034 Uiso 1 1 calc R . . C6 C 0.2526(6) 0.9387(4) 0.8725(2) 0.0310(12) Uani 1 1 d . . . H6A H 0.3067 0.9496 0.9105 0.037 Uiso 1 1 calc R . . H6B H 0.1572 0.9457 0.8839 0.037 Uiso 1 1 calc R . . C7 C 0.2763(5) 0.8441(3) 0.8500(2) 0.0261(11) Uani 1 1 d . . . N3 N 0.3923(5) 0.8051(3) 0.8607(2) 0.0328(11) Uani 1 1 d . . . H3 H 0.4530 0.8350 0.8822 0.039 Uiso 1 1 calc R . . C8 C 0.4236(7) 0.7147(4) 0.8383(3) 0.0473(16) Uani 1 1 d . . . H8A H 0.4011 0.6694 0.8708 0.057 Uiso 1 1 calc R . . H8B H 0.5205 0.7101 0.8294 0.057 Uiso 1 1 calc R . . C9 C 0.3441(7) 0.6950(4) 0.7792(3) 0.0432(15) Uani 1 1 d . . . H9A H 0.3770 0.7338 0.7446 0.052 Uiso 1 1 calc R . . H9B H 0.3562 0.6307 0.7670 0.052 Uiso 1 1 calc R . . C10 C 0.1990(7) 0.7138(4) 0.7907(3) 0.0435(15) Uani 1 1 d . . . H10A H 0.1493 0.7105 0.7507 0.052 Uiso 1 1 calc R . . H10B H 0.1620 0.6672 0.8192 0.052 Uiso 1 1 calc R . . N4 N 0.1824(5) 0.8035(3) 0.8182(2) 0.0334(11) Uani 1 1 d . . . H4 H 0.1055 0.8317 0.8132 0.040 Uiso 1 1 calc R . . C11 C 0.2159(5) 0.4551(3) 0.7761(2) 0.0263(11) Uani 1 1 d . . . C12 C 0.3292(6) 0.4232(4) 0.7467(2) 0.0291(11) Uani 1 1 d . . . H12 H 0.3263 0.4060 0.7039 0.035 Uiso 1 1 calc R . . C13 C 0.4477(6) 0.4167(4) 0.7803(2) 0.0298(12) Uani 1 1 d . . . H13 H 0.5254 0.3974 0.7585 0.036 Uiso 1 1 calc R . . N5 N 0.4600(4) 0.4353(3) 0.84058(19) 0.0241(9) Uani 1 1 d . . . C14 C 0.3485(5) 0.4624(3) 0.8710(2) 0.0209(10) Uani 1 1 d . . . C15 C 0.3562(5) 0.4737(3) 0.9385(2) 0.0204(10) Uani 1 1 d . . . N6 N 0.4741(4) 0.4548(3) 0.9665(2) 0.0258(9) Uani 1 1 d . . . C16 C 0.4777(6) 0.4603(4) 1.0282(2) 0.0311(12) Uani 1 1 d . . . H16 H 0.5598 0.4467 1.0485 0.037 Uiso 1 1 calc R . . C17 C 0.3689(6) 0.4849(4) 1.0656(2) 0.0315(13) Uani 1 1 d . . . H17 H 0.3778 0.4877 1.1098 0.038 Uiso 1 1 calc R . . C18 C 0.2493(5) 0.5050(3) 1.0377(2) 0.0236(10) Uani 1 1 d . . . C19 C 0.2414(5) 0.5009(3) 0.9717(2) 0.0231(10) Uani 1 1 d . . . C20 C 0.1205(5) 0.5200(4) 0.9388(2) 0.0255(11) Uani 1 1 d . . . H20 H 0.0448 0.5417 0.9611 0.031 Uiso 1 1 calc R . . C21 C 0.1119(5) 0.5077(4) 0.8763(2) 0.0270(11) Uani 1 1 d . . . H21 H 0.0297 0.5199 0.8557 0.032 Uiso 1 1 calc R . . C22 C 0.2242(5) 0.4767(3) 0.8405(2) 0.0225(10) Uani 1 1 d . . . C23 C 0.0871(6) 0.4667(4) 0.7395(2) 0.0309(12) Uani 1 1 d . . . O1 O 0.0423(5) 0.3986(4) 0.7138(3) 0.0628(14) Uani 1 1 d . . . O2 O 0.0399(5) 0.5437(3) 0.7376(2) 0.0612(15) Uani 1 1 d . . . C24 C 0.1269(6) 0.5286(4) 1.0758(2) 0.0297(12) Uani 1 1 d . . . O3 O 0.0568(5) 0.4635(3) 1.0932(3) 0.0687(16) Uani 1 1 d . . . O4 O 0.1059(4) 0.6086(3) 1.0870(2) 0.0424(10) Uani 1 1 d . . . C25 C 0.7253(6) 0.3595(4) 0.9024(3) 0.0313(12) Uani 1 1 d . . . H25 H 0.6397 0.3946 0.9046 0.038 Uiso 1 1 calc R . . Cl1 Cl 0.82896(17) 0.39257(13) 0.96552(7) 0.0477(4) Uani 1 1 d . . . Cl2 Cl 0.80547(16) 0.38473(11) 0.83132(6) 0.0427(4) Uani 1 1 d . . . Cl3 Cl 0.68877(17) 0.24300(10) 0.90722(8) 0.0461(4) Uani 1 1 d . . . C26 C 0.7971(8) 0.7259(6) 0.9183(4) 0.073(2) Uani 1 1 d . . . H26 H 0.7412 0.7821 0.9156 0.088 Uiso 1 1 calc R . . Cl4 Cl 0.7046(3) 0.6396(2) 0.95383(15) 0.1189(12) Uani 1 1 d . . . Cl5 Cl 0.8386(3) 0.6894(2) 0.84242(13) 0.0935(8) Uani 1 1 d . . . Cl6 Cl 0.9438(3) 0.7498(2) 0.96013(17) 0.1207(12) 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 C1 0.029(3) 0.032(3) 0.023(2) -0.001(2) 0.0001(19) -0.003(2) N1 0.027(3) 0.022(2) 0.040(2) -0.0069(19) -0.0049(18) 0.0004(19) C2 0.033(3) 0.027(3) 0.050(3) -0.006(3) -0.001(3) 0.001(3) C3 0.037(3) 0.025(3) 0.043(3) -0.005(2) 0.001(3) 0.000(3) C4 0.039(4) 0.031(3) 0.041(3) 0.001(2) -0.005(3) 0.008(3) N2 0.030(3) 0.028(2) 0.034(2) -0.0032(19) -0.0090(19) 0.0011(19) C5 0.035(3) 0.022(3) 0.029(2) -0.003(2) -0.001(2) 0.003(2) C6 0.034(3) 0.030(3) 0.029(3) -0.002(2) 0.004(2) 0.003(2) C7 0.027(3) 0.023(3) 0.029(2) 0.002(2) 0.000(2) -0.002(2) N3 0.029(3) 0.026(2) 0.044(3) -0.008(2) -0.009(2) 0.000(2) C8 0.042(4) 0.038(4) 0.062(4) -0.005(3) -0.014(3) 0.007(3) C9 0.053(4) 0.020(3) 0.057(4) -0.005(3) -0.001(3) -0.001(3) C10 0.041(4) 0.036(3) 0.053(4) -0.003(3) -0.013(3) -0.006(3) N4 0.031(3) 0.020(2) 0.050(3) 0.003(2) -0.011(2) -0.003(2) C11 0.030(3) 0.023(3) 0.026(2) 0.002(2) -0.002(2) -0.005(2) C12 0.038(3) 0.031(3) 0.018(2) -0.001(2) 0.003(2) -0.002(2) C13 0.035(3) 0.032(3) 0.023(2) 0.003(2) 0.009(2) 0.001(2) N5 0.022(2) 0.023(2) 0.028(2) 0.0019(17) 0.0046(16) -0.0002(17) C14 0.017(3) 0.018(2) 0.027(2) -0.0004(19) 0.0038(18) -0.0040(19) C15 0.017(3) 0.018(2) 0.026(2) -0.0015(19) -0.0013(17) -0.0029(19) N6 0.022(2) 0.027(2) 0.028(2) -0.0042(18) -0.0023(17) 0.0016(18) C16 0.025(3) 0.039(3) 0.029(3) -0.005(2) -0.008(2) 0.006(2) C17 0.029(3) 0.044(4) 0.021(2) -0.005(2) -0.002(2) 0.002(3) C18 0.024(3) 0.022(2) 0.025(2) -0.006(2) 0.0029(19) -0.003(2) C19 0.019(3) 0.024(3) 0.027(2) -0.0028(19) 0.0036(18) -0.002(2) C20 0.023(3) 0.023(3) 0.031(2) -0.004(2) 0.0016(19) 0.000(2) C21 0.018(3) 0.033(3) 0.029(2) 0.003(2) -0.0021(19) 0.003(2) C22 0.023(3) 0.021(2) 0.024(2) 0.0047(18) 0.0001(18) -0.004(2) C23 0.030(3) 0.039(3) 0.024(2) -0.001(2) -0.003(2) -0.005(3) O1 0.048(3) 0.052(3) 0.089(4) -0.019(3) -0.023(3) -0.012(3) O2 0.069(4) 0.050(3) 0.065(3) 0.000(2) -0.046(3) 0.010(3) C24 0.031(3) 0.034(3) 0.024(2) -0.003(2) 0.006(2) -0.004(3) O3 0.053(3) 0.046(3) 0.107(4) -0.012(3) 0.043(3) -0.016(3) O4 0.040(3) 0.036(2) 0.051(2) -0.005(2) 0.0182(19) 0.002(2) C25 0.029(3) 0.029(3) 0.036(3) 0.002(2) 0.004(2) 0.003(2) Cl1 0.0409(9) 0.0649(11) 0.0374(7) 0.0000(7) -0.0050(6) -0.0121(8) Cl2 0.0374(8) 0.0565(9) 0.0343(6) 0.0053(7) 0.0062(6) 0.0017(7) Cl3 0.0458(9) 0.0357(8) 0.0567(9) 0.0019(7) 0.0011(7) -0.0039(7) C26 0.055(5) 0.063(5) 0.101(7) 0.016(5) -0.007(5) 0.028(4) Cl4 0.103(2) 0.123(2) 0.130(2) 0.068(2) 0.0365(19) 0.019(2) Cl5 0.0681(16) 0.114(2) 0.0986(18) 0.0165(16) 0.0156(13) 0.0063(15) Cl6 0.097(2) 0.112(2) 0.153(3) -0.007(2) -0.054(2) 0.034(2) _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 C1 N2 1.311(7) . ? C1 N1 1.312(6) . ? C1 C5 1.484(7) . ? N1 C2 1.459(7) . ? N1 H1 0.8800 . ? C2 C3 1.512(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.515(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.461(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N2 H2 0.8800 . ? C5 C6 1.523(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.492(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N4 1.304(7) . ? C7 N3 1.314(7) . ? N3 C8 1.449(8) . ? N3 H3 0.8800 . ? C8 C9 1.521(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.498(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N4 1.456(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N4 H4 0.8800 . ? C11 C12 1.378(7) . ? C11 C22 1.416(7) . ? C11 C23 1.518(7) . ? C12 C13 1.391(8) . ? C12 H12 0.9500 . ? C13 N5 1.323(6) . ? C13 H13 0.9500 . ? N5 C14 1.351(6) . ? C14 C22 1.420(7) . ? C14 C15 1.455(6) . ? C15 N6 1.353(6) . ? C15 C19 1.408(7) . ? N6 C16 1.324(6) . ? C16 C17 1.398(7) . ? C16 H16 0.9500 . ? C17 C18 1.370(7) . ? C17 H17 0.9500 . ? C18 C19 1.414(7) . ? C18 C24 1.512(7) . ? C19 C20 1.428(7) . ? C20 C21 1.351(7) . ? C20 H20 0.9500 . ? C21 C22 1.435(7) . ? C21 H21 0.9500 . ? C23 O1 1.227(7) . ? C23 O2 1.229(7) . ? C24 O4 1.221(7) . ? C24 O3 1.244(7) . ? C25 Cl3 1.757(6) . ? C25 Cl2 1.758(5) . ? C25 Cl1 1.771(6) . ? C25 H25 1.0000 . ? C26 Cl4 1.746(9) . ? C26 Cl6 1.755(9) . ? C26 Cl5 1.759(10) . ? C26 H26 1.0000 . ? 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 C1 N1 122.4(5) . . ? N2 C1 C5 118.8(5) . . ? N1 C1 C5 118.7(5) . . ? C1 N1 C2 121.7(5) . . ? C1 N1 H1 119.1 . . ? C2 N1 H1 119.1 . . ? N1 C2 C3 109.8(5) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 109.6(5) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N2 C4 C3 110.0(5) . . ? N2 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C1 N2 C4 122.7(5) . . ? C1 N2 H2 118.7 . . ? C4 N2 H2 118.7 . . ? C1 C5 C6 111.9(4) . . ? C1 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C1 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 111.8(4) . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? N4 C7 N3 121.8(5) . . ? N4 C7 C6 118.7(5) . . ? N3 C7 C6 119.4(5) . . ? C7 N3 C8 122.3(5) . . ? C7 N3 H3 118.9 . . ? C8 N3 H3 118.9 . . ? N3 C8 C9 109.6(5) . . ? N3 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N3 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C8 109.6(6) . . ? C10 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? C10 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? N4 C10 C9 110.1(5) . . ? N4 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N4 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.2 . . ? C7 N4 C10 123.0(5) . . ? C7 N4 H4 118.5 . . ? C10 N4 H4 118.5 . . ? C12 C11 C22 118.2(5) . . ? C12 C11 C23 120.0(4) . . ? C22 C11 C23 121.8(5) . . ? C11 C12 C13 119.2(4) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? N5 C13 C12 124.7(5) . . ? N5 C13 H13 117.6 . . ? C12 C13 H13 117.6 . . ? C13 N5 C14 117.0(5) . . ? N5 C14 C22 123.0(4) . . ? N5 C14 C15 117.9(4) . . ? C22 C14 C15 119.0(4) . . ? N6 C15 C19 123.0(4) . . ? N6 C15 C14 117.5(4) . . ? C19 C15 C14 119.4(4) . . ? C16 N6 C15 117.0(4) . . ? N6 C16 C17 124.4(5) . . ? N6 C16 H16 117.8 . . ? C17 C16 H16 117.8 . . ? C18 C17 C16 119.0(4) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C17 C18 C19 118.4(4) . . ? C17 C18 C24 121.4(4) . . ? C19 C18 C24 120.2(4) . . ? C15 C19 C18 118.1(5) . . ? C15 C19 C20 119.8(4) . . ? C18 C19 C20 122.1(4) . . ? C21 C20 C19 121.0(5) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.4(5) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C11 C22 C14 117.7(5) . . ? C11 C22 C21 123.0(5) . . ? C14 C22 C21 119.1(4) . . ? O1 C23 O2 126.8(6) . . ? O1 C23 C11 116.7(5) . . ? O2 C23 C11 116.5(5) . . ? O4 C24 O3 126.0(5) . . ? O4 C24 C18 117.9(5) . . ? O3 C24 C18 116.1(5) . . ? Cl3 C25 Cl2 110.6(3) . . ? Cl3 C25 Cl1 110.2(3) . . ? Cl2 C25 Cl1 109.5(3) . . ? Cl3 C25 H25 108.8 . . ? Cl2 C25 H25 108.8 . . ? Cl1 C25 H25 108.8 . . ? Cl4 C26 Cl6 111.5(5) . . ? Cl4 C26 Cl5 107.7(5) . . ? Cl6 C26 Cl5 109.5(5) . . ? Cl4 C26 H26 109.3 . . ? Cl6 C26 H26 109.3 . . ? Cl5 C26 H26 109.3 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.757 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.095 # Attachment '_Ag+-_2,2-_complex.cif' data_e1619a _database_code_depnum_ccdc_archive 'CCDC 729997' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H15 Ag N4 O8, 1.23(C2 H6 O S), 0.77(C2 H6 O)' _chemical_formula_sum 'C32 H27 Ag N4 O10 S' _chemical_formula_weight 767.51 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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/c _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 13.5409(10) _cell_length_b 7.4008(6) _cell_length_c 15.2713(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.533(3) _cell_angle_gamma 90.00 _cell_volume 1499.49(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1201 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.20 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.811 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8949 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12347 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3438 _reflns_number_gt 2469 _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, 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^)+(0.1009P)^2^+9.6919P] 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 3438 _refine_ls_number_parameters 236 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.2058 _refine_ls_wR_factor_gt 0.1812 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.007 _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 1.0000 0.31923(12) 0.7500 0.0370(3) Uani 1 2 d S . . N1 N 0.8770(3) 0.3955(7) 0.8356(3) 0.0219(10) Uani 1 1 d . . . N2 N 1.0570(3) 0.2357(8) 0.8949(3) 0.0300(12) Uani 1 1 d . . . C1 C 0.7866(4) 0.4619(9) 0.8046(4) 0.0280(13) Uani 1 1 d . . . H1 H 0.7693 0.4934 0.7431 0.034 Uiso 1 1 calc R . . C2 C 0.7153(5) 0.4880(10) 0.8572(4) 0.0376(17) Uani 1 1 d . . . H2 H 0.6509 0.5355 0.8315 0.045 Uiso 1 1 calc R . . C3 C 0.7380(6) 0.4450(12) 0.9467(5) 0.049(2) Uani 1 1 d . . . C4 C 0.8348(5) 0.3746(9) 0.9830(4) 0.0312(14) Uani 1 1 d . . . C5 C 0.8684(6) 0.3191(11) 1.0746(4) 0.046(2) Uani 1 1 d . . . H5 H 0.8241 0.3345 1.1151 0.055 Uiso 1 1 calc R . . C6 C 0.9602(5) 0.2461(9) 1.1051(4) 0.0309(14) Uani 1 1 d . . . H6 H 0.9795 0.2141 1.1664 0.037 Uiso 1 1 calc R . . C7 C 1.0286(4) 0.2163(8) 1.0466(3) 0.0205(12) Uani 1 1 d . . . C8 C 1.1261(4) 0.1359(9) 1.0738(4) 0.0261(13) Uani 1 1 d . . . C9 C 1.1830(4) 0.1099(12) 1.0101(4) 0.0436(19) Uani 1 1 d . . . H9 H 1.2482 0.0579 1.0264 0.052 Uiso 1 1 calc R . . C10 C 1.1461(5) 0.1588(13) 0.9218(4) 0.053(2) Uani 1 1 d . . . H10 H 1.1866 0.1362 0.8789 0.064 Uiso 1 1 calc R . . C11 C 0.9986(4) 0.2649(8) 0.9559(3) 0.0205(11) Uani 1 1 d . . . C12 C 0.9007(4) 0.3464(8) 0.9238(3) 0.0212(12) Uani 1 1 d . . . C13 C 0.6597(5) 0.4885(11) 1.0028(4) 0.049 Uani 1 1 d . . . C14 C 1.1683(4) 0.0756(9) 1.1679(4) 0.0293(14) Uani 1 1 d . . . O1 O 0.5699(5) 0.4779(16) 0.9580(5) 0.049(2) Uani 1 1 d . . . O2 O 0.6856(6) 0.5298(14) 1.0816(4) 0.049(2) Uani 1 1 d . . . O3 O 1.1255(5) 0.0816(11) 1.2278(3) 0.049(2) Uani 1 1 d . . . O4 O 1.2589(3) 0.0068(10) 1.1768(3) 0.049(2) Uani 1 1 d . . . S1 S 0.4348(2) 0.9555(5) 0.38307(19) 0.0473(11) Uani 0.617(7) 1 d . . . O5 O 0.3363(15) 0.901(5) 0.3338(13) 0.0473(11) Uani 0.617(7) 1 d . . . C15 C 0.4822(16) 0.779(3) 0.3220(14) 0.086(6) Uani 0.617(7) 1 d . . . H15A H 0.4524 0.6630 0.3343 0.129 Uiso 0.617(7) 1 calc PR . . H15B H 0.5557 0.7719 0.3406 0.129 Uiso 0.617(7) 1 calc PR . . H15C H 0.4643 0.8045 0.2579 0.129 Uiso 0.617(7) 1 calc PR . . C16 C 0.4867(14) 1.141(3) 0.3317(15) 0.087(6) Uani 0.617(7) 1 d . . . H16A H 0.5579 1.1175 0.3317 0.130 Uiso 0.617(7) 1 calc PR . . H16B H 0.4808 1.2523 0.3653 0.130 Uiso 0.617(7) 1 calc PR . . H16C H 0.4497 1.1555 0.2700 0.130 Uiso 0.617(7) 1 calc PR . . C17 C 0.3891(12) 1.146(2) 0.3828(11) 0.032(2) Uani 0.383(7) 1 d . . . H17A H 0.4565 1.1122 0.4153 0.049 Uiso 0.383(7) 1 calc PR . . H17B H 0.3566 1.2239 0.4205 0.049 Uiso 0.383(7) 1 calc PR . . H17C H 0.3947 1.2105 0.3280 0.049 Uiso 0.383(7) 1 calc PR B 2 O8 O 0.3609(14) 0.852(2) 0.3224(16) 0.032(2) Uani 0.383(7) 1 d . . . H8 H 0.3268 0.8418 0.2702 0.049 Uiso 0.383(7) 1 calc PR . . C18 C 0.3301(19) 0.987(3) 0.3603(15) 0.032(2) Uani 0.383(7) 1 d . . . H18A H 0.3129 0.9417 0.4164 0.039 Uiso 0.383(7) 1 calc PR . . H18B H 0.2660 1.0256 0.3216 0.039 Uiso 0.383(7) 1 calc 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 0.0291(4) 0.0690(6) 0.0160(3) 0.000 0.0119(2) 0.000 N1 0.019(2) 0.028(3) 0.019(2) -0.0029(19) 0.0043(17) -0.005(2) N2 0.018(2) 0.059(4) 0.014(2) 0.001(2) 0.0055(17) 0.000(2) C1 0.031(3) 0.035(4) 0.019(3) 0.000(2) 0.007(2) 0.002(3) C2 0.037(3) 0.049(5) 0.030(3) 0.018(3) 0.016(3) 0.022(3) C3 0.051(4) 0.067(6) 0.038(4) 0.029(4) 0.032(3) 0.038(4) C4 0.037(3) 0.035(4) 0.026(3) 0.013(3) 0.017(2) 0.019(3) C5 0.055(4) 0.067(5) 0.024(3) 0.021(3) 0.027(3) 0.038(4) C6 0.039(3) 0.038(4) 0.020(3) 0.005(2) 0.016(2) 0.013(3) C7 0.019(2) 0.025(3) 0.018(2) -0.003(2) 0.0068(19) -0.007(2) C8 0.017(2) 0.039(4) 0.021(3) -0.004(2) 0.002(2) -0.007(2) C9 0.014(3) 0.088(6) 0.028(3) 0.005(3) 0.005(2) 0.003(3) C10 0.018(3) 0.119(8) 0.025(3) 0.009(4) 0.011(2) 0.012(4) C11 0.018(2) 0.029(3) 0.017(2) -0.007(2) 0.0067(19) -0.006(2) C12 0.022(2) 0.026(3) 0.017(2) 0.000(2) 0.0092(19) -0.001(2) C13 0.051 0.068 0.037 0.028 0.031 0.039 C14 0.025(3) 0.041(4) 0.022(3) -0.002(3) 0.003(2) -0.009(3) O1 0.051(4) 0.067(6) 0.038(4) 0.029(4) 0.032(3) 0.038(4) O2 0.051(4) 0.067(6) 0.038(4) 0.029(4) 0.032(3) 0.038(4) O3 0.051(4) 0.067(6) 0.038(4) 0.029(4) 0.032(3) 0.038(4) O4 0.051(4) 0.067(6) 0.038(4) 0.029(4) 0.032(3) 0.038(4) S1 0.0377(16) 0.070(3) 0.0291(15) 0.0022(14) -0.0052(11) -0.0015(15) O5 0.0377(16) 0.070(3) 0.0291(15) 0.0022(14) -0.0052(11) -0.0015(15) C15 0.095(13) 0.079(13) 0.096(14) 0.019(11) 0.047(11) -0.003(11) C16 0.061(10) 0.082(13) 0.122(17) -0.021(11) 0.031(10) -0.019(9) C17 0.031(5) 0.031(5) 0.033(5) 0.005(4) 0.002(4) 0.003(4) O8 0.031(5) 0.031(5) 0.033(5) 0.005(4) 0.002(4) 0.003(4) C18 0.031(5) 0.031(5) 0.033(5) 0.005(4) 0.002(4) 0.003(4) _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 2.279(5) 2_756 ? Ag1 N2 2.279(5) . ? Ag1 N1 2.381(4) . ? Ag1 N1 2.381(4) 2_756 ? N1 C1 1.316(7) . ? N1 C12 1.370(7) . ? N2 C10 1.322(8) . ? N2 C11 1.355(6) . ? C1 C2 1.388(8) . ? C1 H1 0.9500 . ? C2 C3 1.377(9) . ? C2 H2 0.9500 . ? C3 C4 1.417(9) . ? C3 C13 1.524(8) . ? C4 C12 1.407(7) . ? C4 C5 1.441(8) . ? C5 C6 1.350(9) . ? C5 H5 0.9500 . ? C6 C7 1.427(7) . ? C6 H6 0.9500 . ? C7 C11 1.410(7) . ? C7 C8 1.432(8) . ? C8 C9 1.370(8) . ? C8 C14 1.504(8) . ? C9 C10 1.389(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.449(8) . ? C13 O2 1.223(10) . ? C13 O1 1.274(10) . ? C14 O3 1.178(7) . ? C14 O4 1.309(7) . ? S1 O5 1.45(2) . ? S1 C16 1.794(19) . ? S1 C15 1.80(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.43(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O8 C18 1.27(4) . ? O8 H8 0.8400 . ? C18 H18A 0.9900 . ? C18 H18B 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 N2 Ag1 N2 148.5(3) 2_756 . ? N2 Ag1 N1 117.32(16) 2_756 . ? N2 Ag1 N1 70.72(16) . . ? N2 Ag1 N1 70.72(16) 2_756 2_756 ? N2 Ag1 N1 117.32(16) . 2_756 ? N1 Ag1 N1 152.6(2) . 2_756 ? C1 N1 C12 118.1(5) . . ? C1 N1 Ag1 126.4(4) . . ? C12 N1 Ag1 115.1(3) . . ? C10 N2 C11 118.5(5) . . ? C10 N2 Ag1 122.0(4) . . ? C11 N2 Ag1 119.5(4) . . ? N1 C1 C2 123.3(5) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 120.0(6) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 118.6(5) . . ? C2 C3 C13 117.8(6) . . ? C4 C3 C13 123.4(6) . . ? C12 C4 C3 117.3(5) . . ? C12 C4 C5 117.6(5) . . ? C3 C4 C5 124.9(5) . . ? C6 C5 C4 122.6(5) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C7 121.0(5) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C11 C7 C6 118.6(5) . . ? C11 C7 C8 117.4(5) . . ? C6 C7 C8 124.0(5) . . ? C9 C8 C7 117.9(5) . . ? C9 C8 C14 118.5(5) . . ? C7 C8 C14 123.6(5) . . ? C8 C9 C10 120.6(6) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? N2 C10 C9 122.8(6) . . ? N2 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N2 C11 C7 122.7(5) . . ? N2 C11 C12 117.0(5) . . ? C7 C11 C12 120.2(4) . . ? N1 C12 C4 122.6(5) . . ? N1 C12 C11 117.5(4) . . ? C4 C12 C11 119.9(5) . . ? O2 C13 O1 126.8(7) . . ? O2 C13 C3 120.7(7) . . ? O1 C13 C3 112.5(6) . . ? O3 C14 O4 122.1(6) . . ? O3 C14 C8 125.3(6) . . ? O4 C14 C8 112.5(5) . . ? O5 S1 C16 112.6(12) . . ? O5 S1 C15 85.2(14) . . ? C16 S1 C15 96.9(8) . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C18 O8 H8 109.5 . . ? O8 C18 C17 123(2) . . ? O8 C18 H18A 106.6 . . ? C17 C18 H18A 106.6 . . ? O8 C18 H18B 106.6 . . ? C17 C18 H18B 106.6 . . ? H18A C18 H18B 106.6 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.412 _refine_diff_density_min -1.855 _refine_diff_density_rms 0.147