# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound4 _database_code_depnum_ccdc_archive 'CCDC 880745' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Ag F7 N3 O3' _chemical_formula_sum 'C13 H7 Ag F7 N3 O3' _chemical_formula_weight 494.09 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.22210(10) _cell_length_b 11.5994(2) _cell_length_c 31.6633(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3019.77(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 47157 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 1.439 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7240 _exptl_absorpt_correction_T_max 0.9315 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44790 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 29.99 _reflns_number_total 4395 _reflns_number_gt 3356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; N-H bonds were restrained to get an reasonable length 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^)+(0.0387P)^2^+0.0499P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4395 _refine_ls_number_parameters 261 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.005 _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 0.10590(2) 0.383067(13) 0.514813(5) 0.01870(6) Uani 1 1 d . . . F1 F 0.40947(14) 0.68891(10) 0.66999(4) 0.0215(3) Uani 1 1 d . . . F2 F 0.55157(16) 0.64532(10) 0.74460(4) 0.0236(3) Uani 1 1 d . . . F3 F 0.82046(15) 0.32561(10) 0.68475(4) 0.0243(3) Uani 1 1 d . . . F4 F 0.67449(16) 0.36628(10) 0.61080(4) 0.0199(3) Uani 1 1 d . . . F5 F -0.11918(14) 0.28129(11) 0.37403(4) 0.0234(3) Uani 1 1 d . . . F6 F 0.10692(15) 0.35471(12) 0.35266(4) 0.0249(3) Uani 1 1 d . . . F7 F -0.10898(16) 0.45992(11) 0.35572(4) 0.0286(3) Uani 1 1 d . . . O1 O 0.77274(19) 0.47052(12) 0.75353(4) 0.0243(3) Uani 1 1 d . . . O2 O 0.0230(2) 0.32948(12) 0.44719(4) 0.0250(4) Uani 1 1 d . . . O3 O 0.04904(19) 0.51427(13) 0.42711(4) 0.0234(3) Uani 1 1 d . . . N1 N 0.3136(2) 0.50129(14) 0.53505(5) 0.0159(3) Uani 1 1 d . . . N2 N 0.2887(2) 0.63062(15) 0.48011(5) 0.0163(4) Uani 1 1 d D . . H2A H 0.237(3) 0.5840(16) 0.4650(6) 0.021(6) Uiso 1 1 d D . . H2B H 0.330(3) 0.6848(16) 0.4682(6) 0.019(6) Uiso 1 1 d D . . N3 N 0.4197(2) 0.69331(14) 0.53999(5) 0.0163(4) Uani 1 1 d . . . C1 C 0.3419(3) 0.60807(16) 0.51877(6) 0.0153(4) Uani 1 1 d . . . C2 C 0.4811(3) 0.66745(17) 0.57788(6) 0.0169(4) Uani 1 1 d . . . H2C H 0.543(3) 0.7323(19) 0.5921(6) 0.014(5) Uiso 1 1 d . . . C3 C 0.4673(2) 0.55846(17) 0.59604(6) 0.0154(4) Uani 1 1 d . . . C4 C 0.3788(2) 0.47851(18) 0.57282(6) 0.0162(4) Uani 1 1 d . . . H4A H 0.358(3) 0.403(2) 0.5831(7) 0.021(6) Uiso 1 1 d . . . C5 C 0.5393(2) 0.53057(17) 0.63794(6) 0.0150(4) Uani 1 1 d . . . C6 C 0.5119(2) 0.59864(16) 0.67315(6) 0.0168(4) Uani 1 1 d . . . C7 C 0.5839(2) 0.57702(19) 0.71177(7) 0.0181(4) Uani 1 1 d . . . C8 C 0.6910(2) 0.48538(17) 0.71651(6) 0.0180(4) Uani 1 1 d . . . C9 C 0.7165(3) 0.41488(17) 0.68169(6) 0.0177(4) Uani 1 1 d . . . C10 C 0.6419(2) 0.43657(17) 0.64379(6) 0.0166(4) Uani 1 1 d . . . C11 C 0.7183(3) 0.37405(16) 0.77828(7) 0.0225(5) Uani 1 1 d . . . H11A H 0.6015 0.3816 0.7838 0.034 Uiso 1 1 calc R . . H11B H 0.7775 0.3724 0.8051 0.034 Uiso 1 1 calc R . . H11C H 0.7387 0.3024 0.7628 0.034 Uiso 1 1 calc R . . C12 C 0.0195(2) 0.41056(18) 0.42116(6) 0.0176(4) Uani 1 1 d . . . C13 C -0.0268(3) 0.37648(17) 0.37560(6) 0.0180(4) 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 0.02602(10) 0.01384(9) 0.01623(9) -0.00025(6) -0.00240(6) -0.00344(6) F1 0.0214(7) 0.0201(6) 0.0229(6) -0.0052(5) -0.0039(5) 0.0053(5) F2 0.0308(7) 0.0244(6) 0.0157(6) -0.0056(5) -0.0009(5) -0.0033(6) F3 0.0241(7) 0.0211(7) 0.0277(7) 0.0036(5) -0.0058(5) 0.0062(6) F4 0.0227(6) 0.0202(6) 0.0168(6) -0.0021(5) 0.0008(5) 0.0027(5) F5 0.0230(7) 0.0227(7) 0.0245(7) 0.0034(5) -0.0060(5) -0.0075(5) F6 0.0254(7) 0.0285(7) 0.0206(6) -0.0028(5) 0.0073(5) -0.0024(6) F7 0.0365(8) 0.0241(7) 0.0252(7) 0.0065(6) -0.0094(6) 0.0051(6) O1 0.0288(8) 0.0251(8) 0.0190(7) 0.0082(6) -0.0104(7) -0.0100(7) O2 0.0362(9) 0.0222(8) 0.0167(7) 0.0016(6) -0.0038(7) 0.0061(7) O3 0.0234(8) 0.0220(8) 0.0247(8) -0.0021(7) 0.0018(7) -0.0057(7) N1 0.0171(8) 0.0145(8) 0.0161(8) 0.0012(7) -0.0009(7) -0.0002(7) N2 0.0207(9) 0.0149(9) 0.0133(9) 0.0019(7) -0.0021(7) -0.0056(7) N3 0.0175(9) 0.0142(8) 0.0171(8) -0.0003(7) -0.0010(7) 0.0004(7) C1 0.0136(9) 0.0155(10) 0.0167(10) 0.0001(8) 0.0012(7) 0.0020(8) C2 0.0180(10) 0.0162(10) 0.0165(10) -0.0010(8) -0.0001(8) -0.0003(8) C3 0.0161(10) 0.0150(10) 0.0149(9) 0.0010(8) 0.0014(8) 0.0010(8) C4 0.0172(10) 0.0143(10) 0.0172(10) 0.0026(8) 0.0009(8) -0.0006(8) C5 0.0153(10) 0.0140(9) 0.0155(9) 0.0026(8) -0.0010(8) -0.0012(8) C6 0.0157(10) 0.0144(10) 0.0202(10) 0.0021(8) -0.0018(8) -0.0012(8) C7 0.0199(10) 0.0184(10) 0.0160(10) -0.0022(8) 0.0010(8) -0.0053(8) C8 0.0187(10) 0.0191(10) 0.0162(10) 0.0048(8) -0.0041(8) -0.0068(8) C9 0.0171(10) 0.0138(10) 0.0222(11) 0.0051(8) -0.0024(8) -0.0007(8) C10 0.0174(10) 0.0156(10) 0.0167(10) -0.0011(8) 0.0019(8) -0.0022(8) C11 0.0292(12) 0.0216(12) 0.0168(10) 0.0050(8) -0.0013(9) -0.0019(9) C12 0.0137(10) 0.0203(11) 0.0187(10) -0.0020(9) 0.0015(8) 0.0010(8) C13 0.0183(10) 0.0169(10) 0.0189(10) 0.0033(8) 0.0006(8) 0.0010(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 N1 2.2820(17) . ? Ag1 O2 2.3315(14) . ? Ag1 N3 2.3504(17) 7_655 ? Ag1 O3 2.5344(15) 5_566 ? Ag1 Ag1 3.3572(3) 5_566 ? F1 C6 1.348(2) . ? F2 C7 1.334(2) . ? F3 C9 1.346(2) . ? F4 C10 1.352(2) . ? F5 C13 1.341(2) . ? F6 C13 1.342(2) . ? F7 C13 1.338(2) . ? O1 C8 1.362(2) . ? O1 C11 1.438(2) . ? O2 C12 1.251(2) . ? O3 C12 1.242(2) . ? O3 Ag1 2.5344(15) 5_566 ? N1 C4 1.337(2) . ? N1 C1 1.362(2) . ? N2 C1 1.326(2) . ? N2 H2A 0.840(15) . ? N2 H2B 0.808(15) . ? N3 C2 1.336(3) . ? N3 C1 1.356(3) . ? N3 Ag1 2.3504(17) 7_665 ? C2 C3 1.394(3) . ? C2 H2C 1.01(2) . ? C3 C4 1.389(3) . ? C3 C5 1.488(3) . ? C4 H4A 0.95(2) . ? C5 C6 1.385(3) . ? C5 C10 1.391(3) . ? C6 C7 1.381(3) . ? C7 C8 1.388(3) . ? C8 C9 1.389(3) . ? C9 C10 1.371(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.544(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 N1 Ag1 O2 129.55(6) . . ? N1 Ag1 N3 122.31(6) . 7_655 ? O2 Ag1 N3 92.04(6) . 7_655 ? N1 Ag1 O3 83.69(5) . 5_566 ? O2 Ag1 O3 130.15(5) . 5_566 ? N3 Ag1 O3 98.57(5) 7_655 5_566 ? N1 Ag1 Ag1 88.92(4) . 5_566 ? O2 Ag1 Ag1 78.89(4) . 5_566 ? N3 Ag1 Ag1 143.61(4) 7_655 5_566 ? O3 Ag1 Ag1 64.05(3) 5_566 5_566 ? C8 O1 C11 114.44(16) . . ? C12 O2 Ag1 114.29(13) . . ? C12 O3 Ag1 117.82(13) . 5_566 ? C4 N1 C1 116.73(17) . . ? C4 N1 Ag1 115.62(13) . . ? C1 N1 Ag1 124.63(13) . . ? C1 N2 H2A 124.6(15) . . ? C1 N2 H2B 116.5(16) . . ? H2A N2 H2B 117(2) . . ? C2 N3 C1 117.37(17) . . ? C2 N3 Ag1 123.27(13) . 7_665 ? C1 N3 Ag1 118.21(13) . 7_665 ? N2 C1 N3 117.99(18) . . ? N2 C1 N1 118.19(18) . . ? N3 C1 N1 123.82(18) . . ? N3 C2 C3 122.91(19) . . ? N3 C2 H2C 115.0(12) . . ? C3 C2 H2C 122.0(12) . . ? C4 C3 C2 115.47(18) . . ? C4 C3 C5 122.34(18) . . ? C2 C3 C5 122.18(18) . . ? N1 C4 C3 123.47(19) . . ? N1 C4 H4A 114.6(14) . . ? C3 C4 H4A 121.9(14) . . ? C6 C5 C10 116.00(18) . . ? C6 C5 C3 121.96(18) . . ? C10 C5 C3 122.02(17) . . ? F1 C6 C7 118.33(18) . . ? F1 C6 C5 119.00(17) . . ? C7 C6 C5 122.66(19) . . ? F2 C7 C6 119.79(19) . . ? F2 C7 C8 119.78(18) . . ? C6 C7 C8 120.42(19) . . ? O1 C8 C9 122.27(19) . . ? O1 C8 C7 120.20(19) . . ? C9 C8 C7 117.45(18) . . ? F3 C9 C10 119.22(18) . . ? F3 C9 C8 119.47(17) . . ? C10 C9 C8 121.27(19) . . ? F4 C10 C9 118.47(18) . . ? F4 C10 C5 119.35(18) . . ? C9 C10 C5 122.13(19) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 O2 128.6(2) . . ? O3 C12 C13 115.98(18) . . ? O2 C12 C13 115.39(17) . . ? F7 C13 F5 107.01(17) . . ? F7 C13 F6 107.17(16) . . ? F5 C13 F6 106.80(16) . . ? F7 C13 C12 112.27(16) . . ? F5 C13 C12 112.66(16) . . ? F6 C13 C12 110.60(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.572 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.098 data_compound5 _database_code_depnum_ccdc_archive 'CCDC 880746' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 Ag F4 N3 O, C2 H5 OH, C F3 O3 S' _chemical_formula_sum 'C14 H13 Ag F7 N3 O5 S' _chemical_formula_weight 576.20 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 25.2591(8) _cell_length_b 10.5671(3) _cell_length_c 15.0340(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.5966(18) _cell_angle_gamma 90.00 _cell_volume 3900.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 58630 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.963 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 1.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7074 _exptl_absorpt_correction_T_max 0.9073 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34321 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4467 _reflns_number_gt 3619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Disorder of C11 on two positions (55:45). The O-Me bond length of the second part was restraint to get an reasonable length. 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^)+(0.0516P)^2^+3.9616P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4467 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.184523(8) 0.49139(2) 0.199654(14) 0.03894(9) Uani 1 1 d . . . S1 S 0.35184(3) 0.90481(6) 0.05470(4) 0.03587(16) Uani 1 1 d . . . F1 F 0.44200(6) 0.29640(19) 0.14658(11) 0.0474(4) Uani 1 1 d . . . F2 F 0.49750(6) 0.3491(2) 0.02116(13) 0.0535(5) Uani 1 1 d . A . F3 F 0.33300(9) 0.4475(3) -0.19132(12) 0.0701(6) Uani 1 1 d . A . F4 F 0.27778(6) 0.39347(19) -0.06778(11) 0.0505(4) Uani 1 1 d . . . F5 F 0.38565(11) 0.7291(3) -0.0408(2) 0.0923(8) Uani 1 1 d . . . F6 F 0.42393(12) 0.7262(3) 0.1028(3) 0.1157(11) Uani 1 1 d . . . F7 F 0.34118(11) 0.6604(2) 0.0553(2) 0.0879(8) Uani 1 1 d . . . O1 O 0.44959(9) 0.4237(3) -0.14726(15) 0.0581(6) Uani 1 1 d D . . O2 O 0.39687(11) 0.9870(2) 0.05051(17) 0.0565(6) Uani 1 1 d . . . O3 O 0.30592(9) 0.9136(2) -0.02166(14) 0.0533(6) Uani 1 1 d . . . O4 O 0.33932(9) 0.9025(2) 0.14308(14) 0.0498(5) Uani 1 1 d . . . O5 O 0.10102(9) 0.4069(2) 0.12094(18) 0.0513(5) Uani 1 1 d . . . H5 H 0.0974(17) 0.432(4) 0.069(3) 0.073(14) Uiso 1 1 d . . . N1 N 0.25569(8) 0.3659(2) 0.19128(15) 0.0331(5) Uani 1 1 d . . . N2 N 0.25155(12) 0.2540(3) 0.32113(18) 0.0469(6) Uani 1 1 d . . . H2A H 0.2639(13) 0.207(3) 0.363(2) 0.040(9) Uiso 1 1 d . . . H2B H 0.2238(17) 0.302(4) 0.328(3) 0.070(12) Uiso 1 1 d . . . N3 N 0.31350(9) 0.1878(2) 0.24060(15) 0.0338(5) Uani 1 1 d . . . C1 C 0.27418(10) 0.2701(3) 0.25034(17) 0.0338(5) Uani 1 1 d . . . C2 C 0.33934(10) 0.2120(2) 0.17433(17) 0.0322(5) Uani 1 1 d . . . H2C H 0.3678 0.1567 0.1674 0.039 Uiso 1 1 calc R . . C3 C 0.32637(10) 0.3149(2) 0.11501(17) 0.0311(5) Uani 1 1 d . . . C4 C 0.28247(10) 0.3871(2) 0.12567(17) 0.0327(5) Uani 1 1 d . . . H4 H 0.2708 0.4550 0.0844 0.039 Uiso 1 1 calc R . . C5 C 0.35724(10) 0.3425(2) 0.04536(17) 0.0309(5) Uani 1 1 d . . . C6 C 0.41396(11) 0.3330(3) 0.06284(17) 0.0345(6) Uani 1 1 d . A . C7 C 0.44292(11) 0.3611(3) -0.00102(19) 0.0387(6) Uani 1 1 d . . . C8 C 0.41752(12) 0.4011(3) -0.08851(19) 0.0412(6) Uani 1 1 d . A . C9 C 0.36139(12) 0.4106(3) -0.10766(18) 0.0423(6) Uani 1 1 d . . . C10 C 0.33268(10) 0.3824(3) -0.04284(18) 0.0363(6) Uani 1 1 d . A . C11A C 0.4334(3) 0.5187(6) -0.2142(5) 0.0546(18) Uiso 0.556(9) 1 d P A 1 H11A H 0.4601 0.5244 -0.2520 0.082 Uiso 0.556(9) 1 calc PR A 1 H11B H 0.4313 0.6002 -0.1842 0.082 Uiso 0.556(9) 1 calc PR A 1 H11C H 0.3976 0.4974 -0.2531 0.082 Uiso 0.556(9) 1 calc PR A 1 C11B C 0.4326(4) 0.3935(9) -0.2410(4) 0.068(3) Uiso 0.444(9) 1 d PD A 2 H11D H 0.4614 0.4162 -0.2719 0.101 Uiso 0.444(9) 1 calc PR A 2 H11E H 0.3994 0.4408 -0.2684 0.101 Uiso 0.444(9) 1 calc PR A 2 H11F H 0.4253 0.3025 -0.2479 0.101 Uiso 0.444(9) 1 calc PR A 2 C12 C 0.37698(15) 0.7462(3) 0.0424(3) 0.0605(9) Uani 1 1 d . . . C13 C 0.05081(14) 0.4289(4) 0.1481(3) 0.0642(10) Uani 1 1 d . . . H13A H 0.0551 0.4007 0.2121 0.077 Uiso 1 1 calc R . . H13B H 0.0217 0.3773 0.1091 0.077 Uiso 1 1 calc R . . C14 C 0.03400(16) 0.5633(5) 0.1408(3) 0.0758(12) Uani 1 1 d . . . H14A H 0.0630 0.6154 0.1781 0.114 Uiso 1 1 calc R . . H14B H 0.0006 0.5734 0.1627 0.114 Uiso 1 1 calc R . . H14C H 0.0272 0.5903 0.0767 0.114 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 0.03969(14) 0.03883(15) 0.04211(14) -0.00275(8) 0.01727(10) 0.00391(8) S1 0.0395(3) 0.0370(4) 0.0338(3) -0.0024(3) 0.0141(3) -0.0014(3) F1 0.0358(8) 0.0701(12) 0.0367(8) 0.0124(8) 0.0094(7) 0.0095(8) F2 0.0316(8) 0.0759(14) 0.0562(10) 0.0093(10) 0.0171(7) 0.0054(8) F3 0.0600(12) 0.1144(18) 0.0360(10) 0.0226(11) 0.0111(8) 0.0168(13) F4 0.0338(8) 0.0759(13) 0.0403(9) 0.0025(8) 0.0053(7) 0.0051(8) F5 0.1019(19) 0.0814(17) 0.114(2) -0.0331(15) 0.0670(17) 0.0100(14) F6 0.0745(17) 0.106(2) 0.156(3) 0.021(2) 0.0056(18) 0.0471(17) F7 0.1080(19) 0.0372(11) 0.131(2) 0.0012(12) 0.0532(17) -0.0040(12) O1 0.0598(14) 0.0753(17) 0.0492(12) 0.0142(11) 0.0327(11) 0.0048(12) O2 0.0633(15) 0.0615(15) 0.0510(13) -0.0057(10) 0.0262(12) -0.0246(11) O3 0.0529(12) 0.0584(15) 0.0441(11) -0.0056(10) 0.0023(10) 0.0086(11) O4 0.0585(13) 0.0603(14) 0.0368(10) -0.0065(9) 0.0237(9) -0.0130(11) O5 0.0436(12) 0.0559(14) 0.0549(14) -0.0004(11) 0.0127(10) -0.0085(10) N1 0.0322(10) 0.0352(11) 0.0338(11) -0.0004(9) 0.0114(9) 0.0039(9) N2 0.0510(15) 0.0570(17) 0.0382(14) 0.0127(12) 0.0219(12) 0.0171(13) N3 0.0353(11) 0.0332(12) 0.0348(11) 0.0012(9) 0.0121(9) 0.0025(9) C1 0.0326(13) 0.0373(14) 0.0329(13) -0.0017(10) 0.0107(10) -0.0004(11) C2 0.0311(12) 0.0317(13) 0.0355(13) -0.0011(10) 0.0112(10) 0.0011(10) C3 0.0295(12) 0.0339(13) 0.0308(12) -0.0017(10) 0.0086(10) -0.0005(10) C4 0.0343(12) 0.0336(13) 0.0317(12) 0.0007(10) 0.0104(10) 0.0026(11) C5 0.0344(12) 0.0289(13) 0.0306(12) -0.0004(10) 0.0100(10) -0.0004(10) C6 0.0346(13) 0.0360(14) 0.0333(13) 0.0039(10) 0.0089(10) 0.0042(11) C7 0.0343(13) 0.0427(15) 0.0423(15) -0.0004(12) 0.0151(11) 0.0037(12) C8 0.0471(15) 0.0419(16) 0.0395(14) 0.0023(12) 0.0201(12) 0.0001(12) C9 0.0491(16) 0.0486(17) 0.0295(13) 0.0076(12) 0.0102(12) 0.0066(13) C10 0.0321(12) 0.0404(15) 0.0362(13) -0.0011(11) 0.0077(10) 0.0024(11) C12 0.056(2) 0.050(2) 0.080(2) 0.0027(17) 0.0251(19) 0.0111(16) C13 0.0455(18) 0.076(3) 0.072(2) 0.017(2) 0.0152(16) -0.0098(18) C14 0.056(2) 0.086(3) 0.088(3) -0.016(2) 0.020(2) 0.006(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 Ag1 N3 2.257(2) 4 ? Ag1 N1 2.261(2) . ? Ag1 O5 2.340(2) . ? S1 O3 1.430(2) . ? S1 O4 1.437(2) . ? S1 O2 1.444(2) . ? S1 C12 1.817(4) . ? F1 C6 1.348(3) . ? F2 C7 1.346(3) . ? F3 C9 1.350(3) . ? F4 C10 1.354(3) . ? F5 C12 1.332(4) . ? F6 C12 1.330(5) . ? F7 C12 1.327(4) . ? O1 C11B 1.409(5) . ? O1 C8 1.353(3) . ? O1 C11A 1.412(7) . ? O5 C13 1.439(4) . ? O5 H5 0.82(4) . ? N1 C4 1.340(3) . ? N1 C1 1.355(3) . ? N2 C1 1.332(3) . ? N2 H2A 0.80(3) . ? N2 H2B 0.89(4) . ? N3 C2 1.338(3) . ? N3 C1 1.354(3) . ? N3 Ag1 2.257(2) 4_545 ? C2 C3 1.395(4) . ? C2 H2C 0.9500 . ? C3 C4 1.386(3) . ? C3 C5 1.474(3) . ? C4 H4 0.9500 . ? C5 C10 1.391(4) . ? C5 C6 1.398(4) . ? C6 C7 1.369(4) . ? C7 C8 1.387(4) . ? C8 C9 1.382(4) . ? C9 C10 1.377(4) . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C13 C14 1.479(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ag1 N1 128.16(8) 4 . ? N3 Ag1 O5 119.03(8) 4 . ? N1 Ag1 O5 112.46(8) . . ? O3 S1 O4 115.48(13) . . ? O3 S1 O2 115.10(15) . . ? O4 S1 O2 113.42(14) . . ? O3 S1 C12 102.44(16) . . ? O4 S1 C12 103.67(16) . . ? O2 S1 C12 104.63(16) . . ? C11B O1 C8 121.7(4) . . ? C11B O1 C11A 58.6(5) . . ? C8 O1 C11A 118.3(3) . . ? C13 O5 Ag1 123.0(2) . . ? C13 O5 H5 108(3) . . ? Ag1 O5 H5 104(3) . . ? C4 N1 C1 116.8(2) . . ? C4 N1 Ag1 119.26(17) . . ? C1 N1 Ag1 123.91(17) . . ? C1 N2 H2A 123(2) . . ? C1 N2 H2B 122(3) . . ? H2A N2 H2B 115(3) . . ? C2 N3 C1 117.1(2) . . ? C2 N3 Ag1 120.22(17) . 4_545 ? C1 N3 Ag1 119.73(17) . 4_545 ? N2 C1 N3 117.9(2) . . ? N2 C1 N1 118.2(2) . . ? N3 C1 N1 123.9(2) . . ? N3 C2 C3 122.9(2) . . ? N3 C2 H2C 118.6 . . ? C3 C2 H2C 118.6 . . ? C4 C3 C2 115.4(2) . . ? C4 C3 C5 123.0(2) . . ? C2 C3 C5 121.6(2) . . ? N1 C4 C3 123.3(2) . . ? N1 C4 H4 118.3 . . ? C3 C4 H4 118.3 . . ? C10 C5 C6 114.1(2) . . ? C10 C5 C3 123.1(2) . . ? C6 C5 C3 122.8(2) . . ? F1 C6 C7 117.8(2) . . ? F1 C6 C5 119.1(2) . . ? C7 C6 C5 123.0(2) . . ? F2 C7 C6 119.4(2) . . ? F2 C7 C8 118.8(2) . . ? C6 C7 C8 121.8(2) . . ? O1 C8 C9 126.4(3) . . ? O1 C8 C7 117.3(3) . . ? C9 C8 C7 116.3(2) . . ? F3 C9 C10 117.9(3) . . ? F3 C9 C8 120.6(2) . . ? C10 C9 C8 121.5(2) . . ? F4 C10 C9 117.4(2) . . ? F4 C10 C5 119.2(2) . . ? C9 C10 C5 123.3(2) . . ? O1 C11A H11A 109.5 . . ? O1 C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? O1 C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? O1 C11B H11D 109.5 . . ? O1 C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? O1 C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? F7 C12 F6 108.7(3) . . ? F7 C12 F5 108.2(3) . . ? F6 C12 F5 107.6(3) . . ? F7 C12 S1 110.5(2) . . ? F6 C12 S1 110.7(3) . . ? F5 C12 S1 111.1(3) . . ? O5 C13 C14 113.0(3) . . ? O5 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? O5 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.585 _refine_diff_density_min -0.845 _refine_diff_density_rms 0.084 data_compound6 _database_code_depnum_ccdc_archive 'CCDC 880747' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 Ag Cl F4 N3 O5' _chemical_formula_sum 'C11 H7 Ag Cl F4 N3 O5' _chemical_formula_weight 480.52 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.31770(10) _cell_length_b 12.76150(10) _cell_length_c 29.9513(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2797.00(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 51258 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 1.715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7254 _exptl_absorpt_correction_T_max 0.8472 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48584 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3208 _reflns_number_gt 2976 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0210P)^2^+2.2200P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3208 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0209 _refine_ls_R_factor_gt 0.0187 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0457 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.191509(18) 0.222301(9) 0.046992(4) 0.01600(5) Uani 1 1 d . . . Cl1 Cl 0.23488(6) 0.22718(3) -0.064279(14) 0.01668(9) Uani 1 1 d . . . F1 F 0.22179(14) 0.63145(7) 0.20118(3) 0.0187(2) Uani 1 1 d . . . F2 F 0.24302(16) 0.62777(8) 0.28860(3) 0.0221(2) Uani 1 1 d . . . F3 F 0.53303(15) 0.29547(8) 0.28122(4) 0.0216(2) Uani 1 1 d . . . F4 F 0.51373(15) 0.30194(8) 0.19200(3) 0.0208(2) Uani 1 1 d . . . O1 O 0.41211(19) 0.44666(10) 0.33256(4) 0.0234(3) Uani 1 1 d . . . O2 O 0.35176(19) 0.23672(12) -0.02451(4) 0.0289(3) Uani 1 1 d . . . O3 O 0.0910(2) 0.30362(11) -0.06045(5) 0.0304(3) Uani 1 1 d . . . O4 O 0.34385(18) 0.24612(11) -0.10310(4) 0.0231(3) Uani 1 1 d . . . O5 O 0.15959(19) 0.12336(10) -0.06483(5) 0.0253(3) Uani 1 1 d . . . N1 N 0.2446(2) 0.38101(10) 0.07709(5) 0.0151(3) Uani 1 1 d . . . N2 N 0.2440(2) 0.47266(13) 0.01065(5) 0.0220(3) Uani 1 1 d . . . H2A H 0.267(3) 0.522(2) -0.0055(9) 0.033(7) Uiso 1 1 d . . . H2B H 0.204(3) 0.4238(19) -0.0025(7) 0.020(6) Uiso 1 1 d . . . N3 N 0.3366(2) 0.56054(10) 0.07422(5) 0.0152(3) Uani 1 1 d . . . C1 C 0.2767(2) 0.47140(13) 0.05452(6) 0.0158(3) Uani 1 1 d . . . C2 C 0.3722(2) 0.55642(12) 0.11810(6) 0.0153(3) Uani 1 1 d . . . H2C H 0.418(3) 0.6209(16) 0.1301(7) 0.021(5) Uiso 1 1 d . . . C3 C 0.3419(2) 0.46810(12) 0.14395(6) 0.0150(3) Uani 1 1 d . . . C4 C 0.2748(2) 0.38163(13) 0.12109(6) 0.0158(3) Uani 1 1 d . . . H4 H 0.244(3) 0.3194(16) 0.1366(7) 0.015(5) Uiso 1 1 d . . . C5 C 0.3673(2) 0.46711(12) 0.19285(6) 0.0150(3) Uani 1 1 d . . . C6 C 0.3054(2) 0.54833(13) 0.22001(6) 0.0156(3) Uani 1 1 d . . . C7 C 0.3151(2) 0.54630(13) 0.26610(6) 0.0165(3) Uani 1 1 d . . . C8 C 0.3915(2) 0.46085(13) 0.28832(6) 0.0170(3) Uani 1 1 d . . . C9 C 0.4551(2) 0.37875(12) 0.26133(6) 0.0171(3) Uani 1 1 d . . . C10 C 0.4444(2) 0.38243(12) 0.21558(6) 0.0168(3) Uani 1 1 d . . . C11 C 0.3799(3) 0.53185(16) 0.36320(6) 0.0228(4) Uani 1 1 d . . . H11A H 0.450(3) 0.5944(17) 0.3547(7) 0.026(6) Uiso 1 1 d . . . H11B H 0.416(3) 0.5063(19) 0.3904(8) 0.035(6) Uiso 1 1 d . . . H11C H 0.250(3) 0.5470(18) 0.3647(8) 0.032(6) Uiso 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 0.02139(8) 0.00972(7) 0.01688(8) 0.00049(4) 0.00118(5) -0.00078(4) Cl1 0.01688(19) 0.01643(19) 0.01672(19) 0.00092(14) 0.00128(16) -0.00214(15) F1 0.0218(5) 0.0128(4) 0.0215(5) 0.0016(4) -0.0046(4) 0.0030(4) F2 0.0263(5) 0.0179(5) 0.0222(5) -0.0050(4) -0.0034(5) 0.0041(4) F3 0.0239(5) 0.0152(4) 0.0257(5) 0.0058(4) -0.0060(4) 0.0031(4) F4 0.0232(5) 0.0143(4) 0.0249(5) -0.0013(4) -0.0002(4) 0.0043(4) O1 0.0317(7) 0.0220(6) 0.0165(6) 0.0014(5) -0.0059(5) 0.0006(5) O2 0.0227(7) 0.0496(9) 0.0143(6) -0.0019(6) 0.0001(5) -0.0113(6) O3 0.0254(7) 0.0229(6) 0.0429(8) 0.0030(6) 0.0084(6) 0.0056(6) O4 0.0240(7) 0.0293(6) 0.0161(6) 0.0014(5) 0.0043(5) -0.0027(6) O5 0.0248(7) 0.0171(6) 0.0339(8) 0.0032(5) -0.0039(6) -0.0055(5) N1 0.0166(7) 0.0110(6) 0.0175(7) -0.0001(5) 0.0021(6) -0.0008(5) N2 0.0349(9) 0.0129(7) 0.0183(8) 0.0016(6) -0.0027(7) -0.0042(7) N3 0.0158(7) 0.0098(6) 0.0199(7) 0.0008(5) -0.0002(6) -0.0003(5) C1 0.0137(8) 0.0133(8) 0.0204(8) 0.0013(6) 0.0017(6) 0.0003(6) C2 0.0128(8) 0.0109(7) 0.0222(8) 0.0003(6) -0.0008(6) 0.0000(6) C3 0.0128(8) 0.0140(7) 0.0181(8) 0.0009(6) 0.0007(6) 0.0006(6) C4 0.0152(8) 0.0124(7) 0.0200(8) 0.0016(6) 0.0023(6) -0.0003(6) C5 0.0130(7) 0.0131(7) 0.0189(8) 0.0009(6) -0.0019(6) -0.0029(6) C6 0.0133(8) 0.0116(7) 0.0218(8) 0.0025(6) -0.0044(6) -0.0007(6) C7 0.0138(8) 0.0139(7) 0.0217(8) -0.0034(6) -0.0019(6) -0.0018(6) C8 0.0144(8) 0.0176(8) 0.0190(8) 0.0019(6) -0.0031(6) -0.0037(6) C9 0.0157(8) 0.0127(7) 0.0229(9) 0.0048(6) -0.0041(6) -0.0012(6) C10 0.0147(8) 0.0120(7) 0.0237(8) -0.0012(6) -0.0003(7) -0.0013(6) C11 0.0208(9) 0.0301(10) 0.0176(9) -0.0020(7) 0.0010(7) 0.0031(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 N3 2.2292(13) 7_655 ? Ag1 N1 2.2507(14) . ? Ag1 O2 2.4484(14) . ? Cl1 O4 1.4304(13) . ? Cl1 O5 1.4350(13) . ? Cl1 O3 1.4397(14) . ? Cl1 O2 1.4715(14) . ? F1 C6 1.3480(18) . ? F2 C7 1.3466(19) . ? F3 C9 1.3453(18) . ? F4 C10 1.3459(19) . ? O1 C8 1.346(2) . ? O1 C11 1.442(2) . ? N1 C4 1.336(2) . ? N1 C1 1.358(2) . ? N2 C1 1.335(2) . ? N2 H2A 0.81(3) . ? N2 H2B 0.79(2) . ? N3 C2 1.341(2) . ? N3 C1 1.355(2) . ? N3 Ag1 2.2291(13) 7_665 ? C2 C3 1.385(2) . ? C2 H2C 0.96(2) . ? C3 C4 1.389(2) . ? C3 C5 1.476(2) . ? C4 H4 0.95(2) . ? C5 C6 1.393(2) . ? C5 C10 1.396(2) . ? C6 C7 1.383(3) . ? C7 C8 1.395(2) . ? C8 C9 1.403(2) . ? C9 C10 1.373(2) . ? C11 H11A 0.98(2) . ? C11 H11B 0.92(2) . ? C11 H11C 0.97(2) . ? 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 N3 Ag1 N1 134.65(5) 7_655 . ? N3 Ag1 O2 115.71(5) 7_655 . ? N1 Ag1 O2 101.54(5) . . ? O4 Cl1 O5 111.15(9) . . ? O4 Cl1 O3 110.96(8) . . ? O5 Cl1 O3 110.23(9) . . ? O4 Cl1 O2 108.66(8) . . ? O5 Cl1 O2 107.99(8) . . ? O3 Cl1 O2 107.72(9) . . ? C8 O1 C11 120.46(14) . . ? Cl1 O2 Ag1 115.05(8) . . ? C4 N1 C1 117.23(14) . . ? C4 N1 Ag1 115.40(11) . . ? C1 N1 Ag1 126.51(11) . . ? C1 N2 H2A 123.8(18) . . ? C1 N2 H2B 123.1(16) . . ? H2A N2 H2B 113(2) . . ? C2 N3 C1 117.20(14) . . ? C2 N3 Ag1 114.38(11) . 7_665 ? C1 N3 Ag1 126.05(11) . 7_665 ? N2 C1 N3 118.46(15) . . ? N2 C1 N1 117.99(15) . . ? N3 C1 N1 123.54(16) . . ? N3 C2 C3 123.27(15) . . ? N3 C2 H2C 113.8(12) . . ? C3 C2 H2C 122.9(12) . . ? C2 C3 C4 115.31(16) . . ? C2 C3 C5 122.77(15) . . ? C4 C3 C5 121.81(15) . . ? N1 C4 C3 123.34(15) . . ? N1 C4 H4 116.0(12) . . ? C3 C4 H4 120.6(12) . . ? C6 C5 C10 115.01(15) . . ? C6 C5 C3 122.11(15) . . ? C10 C5 C3 122.76(15) . . ? F1 C6 C7 117.11(15) . . ? F1 C6 C5 119.27(15) . . ? C7 C6 C5 123.52(16) . . ? F2 C7 C6 117.72(15) . . ? F2 C7 C8 121.47(16) . . ? C6 C7 C8 120.78(16) . . ? O1 C8 C7 128.31(16) . . ? O1 C8 C9 115.46(15) . . ? C7 C8 C9 116.23(16) . . ? F3 C9 C10 119.54(15) . . ? F3 C9 C8 118.38(15) . . ? C10 C9 C8 122.05(15) . . ? F4 C10 C9 118.42(15) . . ? F4 C10 C5 119.17(15) . . ? C9 C10 C5 122.41(16) . . ? O1 C11 H11A 111.1(13) . . ? O1 C11 H11B 104.5(15) . . ? H11A C11 H11B 112(2) . . ? O1 C11 H11C 109.9(14) . . ? H11A C11 H11C 111.3(19) . . ? H11B C11 H11C 108(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.374 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.072 data_compound7 _database_code_depnum_ccdc_archive 'CCDC 880748' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 Ag F4 N4 O4' _chemical_formula_sum 'C11 H7 Ag F4 N4 O4' _chemical_formula_weight 443.08 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.417(7) _cell_length_b 6.3990(8) _cell_length_c 11.262(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.79(3) _cell_angle_gamma 90.00 _cell_volume 1320.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 3.65 _cell_measurement_theta_max 19.30 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.607 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6442 _exptl_absorpt_correction_T_max 0.9686 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29741 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3036 _reflns_number_gt 2714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0269P)^2^+1.6532P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3036 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.395864(9) 1.32433(2) 0.424420(13) 0.01495(7) Uani 1 1 d . . . F1 F 0.16574(7) 0.4951(2) 0.15230(12) 0.0204(3) Uani 1 1 d . . . F2 F 0.06975(7) 0.5078(2) -0.03921(12) 0.0240(3) Uani 1 1 d . . . F3 F 0.15192(8) 1.1832(2) -0.13089(12) 0.0226(3) Uani 1 1 d . . . F4 F 0.25041(8) 1.1686(2) 0.05596(12) 0.0200(3) Uani 1 1 d . . . O1 O 0.05869(9) 0.8539(3) -0.19038(15) 0.0254(4) Uani 1 1 d . . . O2 O 0.47510(9) 1.1135(3) 0.29456(14) 0.0199(3) Uani 1 1 d . . . O3 O 0.39546(8) 1.2827(3) 0.17557(14) 0.0171(3) Uani 1 1 d . . . O4 O 0.47531(9) 1.0825(3) 0.10178(13) 0.0176(3) Uani 1 1 d . . . N1 N 0.32706(10) 1.0114(3) 0.39040(16) 0.0149(4) Uani 1 1 d . . . N2 N 0.40096(11) 0.8233(3) 0.52810(18) 0.0164(4) Uani 1 1 d . . . H2A H 0.4083(13) 0.932(4) 0.566(2) 0.011(6) Uiso 1 1 d . . . H2B H 0.4213(16) 0.719(5) 0.545(3) 0.021(8) Uiso 1 1 d . . . N3 N 0.34532(10) 0.6431(3) 0.36544(16) 0.0142(4) Uani 1 1 d . . . N4 N 0.44888(10) 1.1613(3) 0.19169(16) 0.0132(4) Uani 1 1 d . . . C1 C 0.35750(12) 0.8256(3) 0.42643(19) 0.0138(4) Uani 1 1 d . . . C2 C 0.30066(12) 0.6501(4) 0.2649(2) 0.0153(4) Uani 1 1 d . . . H2C H 0.2953(13) 0.528(4) 0.220(2) 0.012(6) Uiso 1 1 d . . . C3 C 0.26391(12) 0.8305(3) 0.22429(19) 0.0137(4) Uani 1 1 d . . . C4 C 0.27991(12) 1.0092(4) 0.29263(19) 0.0156(4) Uani 1 1 d . . . H4 H 0.2570(14) 1.140(4) 0.271(2) 0.012(6) Uiso 1 1 d . . . C5 C 0.21167(12) 0.8340(3) 0.11496(19) 0.0148(4) Uani 1 1 d . . . C6 C 0.16417(13) 0.6683(3) 0.0842(2) 0.0170(4) Uani 1 1 d . . . C7 C 0.11370(13) 0.6739(4) -0.0155(2) 0.0190(5) Uani 1 1 d . . . C8 C 0.10705(13) 0.8465(4) -0.0901(2) 0.0193(5) Uani 1 1 d . . . C9 C 0.15449(12) 1.0123(4) -0.06140(19) 0.0169(4) Uani 1 1 d . . . C10 C 0.20547(12) 1.0033(4) 0.03746(19) 0.0163(4) Uani 1 1 d . . . C11 C -0.01676(15) 0.8712(5) -0.1676(3) 0.0301(6) Uani 1 1 d . . . H11A H -0.031(2) 0.769(7) -0.117(4) 0.052(11) Uiso 1 1 d . . . H11B H -0.0452(19) 0.870(5) -0.243(3) 0.041(9) Uiso 1 1 d . . . H11C H -0.022(2) 1.015(7) -0.131(4) 0.061(12) Uiso 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 0.02116(10) 0.01255(10) 0.01037(9) -0.00100(6) -0.00221(6) 0.00127(6) F1 0.0227(7) 0.0173(7) 0.0204(7) 0.0029(5) -0.0011(5) -0.0025(5) F2 0.0242(7) 0.0249(8) 0.0218(7) -0.0032(6) -0.0036(6) -0.0088(6) F3 0.0260(7) 0.0249(8) 0.0158(7) 0.0062(5) -0.0037(6) -0.0007(6) F4 0.0217(7) 0.0189(7) 0.0182(7) 0.0016(5) -0.0033(5) -0.0051(5) O1 0.0198(8) 0.0427(11) 0.0124(8) 0.0017(7) -0.0055(6) -0.0049(8) O2 0.0235(8) 0.0250(9) 0.0100(7) -0.0006(6) -0.0037(6) 0.0039(7) O3 0.0170(8) 0.0171(8) 0.0168(8) 0.0024(6) 0.0003(6) 0.0024(6) O4 0.0217(8) 0.0207(8) 0.0106(7) -0.0034(6) 0.0022(6) 0.0006(6) N1 0.0175(9) 0.0137(9) 0.0132(8) -0.0008(7) -0.0001(7) 0.0016(7) N2 0.0224(10) 0.0126(10) 0.0131(9) -0.0022(8) -0.0043(7) 0.0027(8) N3 0.0166(9) 0.0139(9) 0.0116(8) 0.0002(7) -0.0015(7) 0.0013(7) N4 0.0143(8) 0.0136(9) 0.0113(8) -0.0009(6) -0.0012(7) -0.0015(7) C1 0.0170(10) 0.0148(11) 0.0100(10) 0.0009(7) 0.0029(8) 0.0002(8) C2 0.0160(10) 0.0157(11) 0.0143(10) -0.0022(8) 0.0020(8) -0.0007(8) C3 0.0141(10) 0.0159(11) 0.0109(10) 0.0013(8) 0.0000(8) -0.0005(8) C4 0.0158(10) 0.0152(11) 0.0154(10) 0.0002(8) 0.0003(8) 0.0016(9) C5 0.0148(10) 0.0176(11) 0.0118(10) -0.0025(8) 0.0003(8) 0.0027(8) C6 0.0185(11) 0.0185(12) 0.0142(10) 0.0001(8) 0.0018(8) 0.0016(9) C7 0.0160(11) 0.0229(12) 0.0179(11) -0.0057(9) 0.0006(9) -0.0045(9) C8 0.0168(11) 0.0285(13) 0.0119(10) -0.0019(9) -0.0013(8) -0.0018(9) C9 0.0193(10) 0.0197(11) 0.0116(10) 0.0024(8) 0.0009(8) 0.0022(9) C10 0.0159(10) 0.0187(11) 0.0142(10) -0.0023(8) 0.0014(8) -0.0009(9) C11 0.0214(12) 0.0448(17) 0.0225(13) 0.0074(12) -0.0060(10) -0.0011(12) _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 N3 2.3114(19) 1_565 ? Ag1 N1 2.3799(19) . ? Ag1 O4 2.4281(18) 4_586 ? Ag1 O2 2.5533(18) . ? F1 C6 1.347(3) . ? F2 C7 1.346(3) . ? F3 C9 1.343(3) . ? F4 C10 1.346(3) . ? O1 C8 1.367(3) . ? O1 C11 1.443(3) . ? O2 N4 1.247(2) . ? O3 N4 1.253(2) . ? O4 N4 1.271(2) . ? O4 Ag1 2.4282(18) 4_585 ? N1 C4 1.332(3) . ? N1 C1 1.359(3) . ? N2 C1 1.329(3) . ? N2 H2A 0.82(3) . ? N2 H2B 0.78(3) . ? N3 C2 1.331(3) . ? N3 C1 1.362(3) . ? N3 Ag1 2.3114(19) 1_545 ? C2 C3 1.392(3) . ? C2 H2C 0.93(3) . ? C3 C4 1.393(3) . ? C3 C5 1.484(3) . ? C4 H4 0.96(3) . ? C5 C10 1.389(3) . ? C5 C6 1.396(3) . ? C6 C7 1.384(3) . ? C7 C8 1.386(3) . ? C8 C9 1.391(3) . ? C9 C10 1.383(3) . ? C11 H11A 0.93(4) . ? C11 H11B 0.95(4) . ? C11 H11C 1.02(4) . ? 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 N3 Ag1 N1 120.24(7) 1_565 . ? N3 Ag1 O4 102.21(6) 1_565 4_586 ? N1 Ag1 O4 127.29(6) . 4_586 ? N3 Ag1 O2 122.58(6) 1_565 . ? N1 Ag1 O2 77.82(6) . . ? O4 Ag1 O2 105.61(6) 4_586 . ? C8 O1 C11 114.47(19) . . ? N4 O2 Ag1 102.27(13) . . ? N4 O4 Ag1 108.09(13) . 4_585 ? C4 N1 C1 116.91(19) . . ? C4 N1 Ag1 115.72(15) . . ? C1 N1 Ag1 119.42(14) . . ? C1 N2 H2A 119.4(18) . . ? C1 N2 H2B 117(2) . . ? H2A N2 H2B 123(3) . . ? C2 N3 C1 117.12(19) . . ? C2 N3 Ag1 118.08(15) . 1_545 ? C1 N3 Ag1 124.80(14) . 1_545 ? O2 N4 O3 120.76(18) . . ? O2 N4 O4 119.96(18) . . ? O3 N4 O4 119.27(18) . . ? N2 C1 N1 117.5(2) . . ? N2 C1 N3 118.6(2) . . ? N1 C1 N3 123.9(2) . . ? N3 C2 C3 123.1(2) . . ? N3 C2 H2C 117.3(15) . . ? C3 C2 H2C 119.6(16) . . ? C2 C3 C4 115.5(2) . . ? C2 C3 C5 122.6(2) . . ? C4 C3 C5 121.94(19) . . ? N1 C4 C3 123.3(2) . . ? N1 C4 H4 115.9(16) . . ? C3 C4 H4 120.8(16) . . ? C10 C5 C6 115.3(2) . . ? C10 C5 C3 122.6(2) . . ? C6 C5 C3 122.1(2) . . ? F1 C6 C7 117.2(2) . . ? F1 C6 C5 120.5(2) . . ? C7 C6 C5 122.3(2) . . ? F2 C7 C6 118.8(2) . . ? F2 C7 C8 119.7(2) . . ? C6 C7 C8 121.6(2) . . ? O1 C8 C7 122.6(2) . . ? O1 C8 C9 120.5(2) . . ? C7 C8 C9 116.9(2) . . ? F3 C9 C10 119.0(2) . . ? F3 C9 C8 120.09(19) . . ? C10 C9 C8 120.9(2) . . ? F4 C10 C9 116.6(2) . . ? F4 C10 C5 120.36(19) . . ? C9 C10 C5 123.0(2) . . ? O1 C11 H11A 113(2) . . ? O1 C11 H11B 107(2) . . ? H11A C11 H11B 112(3) . . ? O1 C11 H11C 106(2) . . ? H11A C11 H11C 111(3) . . ? H11B C11 H11C 108(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.689 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.094 _vrf_PLAT222_ion35 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.55 Ratio RESPONSE: hydrogens were refined isotropically. ; data__compoundNFAP _database_code_depnum_ccdc_archive 'CCDC 880749' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 F4 N4' _chemical_formula_sum 'C12 H10 F4 N4' _chemical_formula_weight 286.24 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d d' _symmetry_space_group_name_Hall '-F 2uv 2vw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/4, -y+1/4, z' 'x, -y+1/4, -z+1/4' '-x+1/4, y, -z+1/4' 'x, y+1/2, z+1/2' '-x+1/4, -y+3/4, z+1/2' 'x, -y+3/4, -z+3/4' '-x+1/4, y+1/2, -z+3/4' 'x+1/2, y, z+1/2' '-x+3/4, -y+1/4, z+1/2' 'x+1/2, -y+1/4, -z+3/4' '-x+3/4, y, -z+3/4' 'x+1/2, y+1/2, z' '-x+3/4, -y+3/4, z' 'x+1/2, -y+3/4, -z+1/4' '-x+3/4, y+1/2, -z+1/4' '-x, -y, -z' 'x-1/4, y-1/4, -z' '-x, y-1/4, z-1/4' 'x-1/4, -y, z-1/4' '-x, -y+1/2, -z+1/2' 'x-1/4, y+1/4, -z+1/2' '-x, y+1/4, z+1/4' 'x-1/4, -y+1/2, z+1/4' '-x+1/2, -y, -z+1/2' 'x+1/4, y-1/4, -z+1/2' '-x+1/2, y-1/4, z+1/4' 'x+1/4, -y, z+1/4' '-x+1/2, -y+1/2, -z' 'x+1/4, y+1/4, -z' '-x+1/2, y+1/4, z-1/4' 'x+1/4, -y+1/2, z-1/4' _cell_length_a 7.4891(19) _cell_length_b 13.333(2) _cell_length_c 51.316(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5124.1(18) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 47 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9609 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ; _diffrn_ambient_temperature 296(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15596 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -59 _diffrn_reflns_limit_l_max 60 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1127 _reflns_number_gt 847 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0512P)^2^+3.9733P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1127 _refine_ls_number_parameters 99 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 F1 F 0.19254(16) 0.23085(9) 0.23089(2) 0.0658(4) Uani 1 1 d . . . F2 F 0.19230(17) 0.23014(10) 0.28189(2) 0.0744(4) Uani 1 1 d . . . N1 N 0.21882(19) 0.35650(13) 0.15908(3) 0.0532(5) Uani 1 1 d . . . N2 N 0.3750 0.3750 0.12083(5) 0.0727(9) Uani 1 2 d S . . H2N H 0.476(3) 0.390(2) 0.1122(5) 0.088(8) Uiso 1 1 d . . . N3 N 0.3750 0.3750 0.31137(5) 0.0929(10) Uani 1 2 d S . . C1 C 0.3750 0.3750 0.14690(5) 0.0516(7) Uani 1 2 d S . . C2 C 0.2228(2) 0.35689(15) 0.18495(4) 0.0504(5) Uani 1 1 d . . . H2A H 0.1169 0.3442 0.1938 0.061 Uiso 1 1 calc R . . C3 C 0.3750 0.3750 0.19956(5) 0.0453(6) Uani 1 2 d S . . C4 C 0.3750 0.3750 0.22843(5) 0.0436(6) Uani 1 2 d S . . C5 C 0.2810(2) 0.30521(15) 0.24306(4) 0.0483(5) Uani 1 1 d . . . C6 C 0.2813(3) 0.30487(15) 0.26975(4) 0.0534(5) Uani 1 1 d . . . C7 C 0.3750 0.3750 0.28451(5) 0.0555(7) Uani 1 2 d S . . C8 C 0.2138(5) 0.3575(2) 0.32588(5) 0.1022(11) Uani 1 1 d . . . H8A H 0.1131 0.3603 0.3143 0.153 Uiso 1 1 calc R . . H8B H 0.2014 0.4080 0.3391 0.153 Uiso 1 1 calc R . . H8C H 0.2192 0.2926 0.3339 0.153 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 F1 0.0609(8) 0.0582(7) 0.0782(9) 0.0036(6) -0.0092(6) -0.0126(6) F2 0.0689(8) 0.0774(9) 0.0768(9) 0.0281(7) 0.0057(6) -0.0038(7) N1 0.0351(9) 0.0744(12) 0.0501(10) -0.0043(8) 0.0010(7) 0.0037(8) N2 0.0422(15) 0.128(3) 0.0480(16) 0.000 0.000 -0.0026(16) N3 0.087(2) 0.139(3) 0.0519(16) 0.000 0.000 0.014(2) C1 0.0368(15) 0.0657(18) 0.0523(17) 0.000 0.000 0.0073(13) C2 0.0356(10) 0.0609(13) 0.0548(12) -0.0021(9) 0.0037(9) 0.0041(9) C3 0.0361(14) 0.0470(15) 0.0527(16) 0.000 0.000 0.0053(12) C4 0.0354(14) 0.0436(14) 0.0519(15) 0.000 0.000 0.0077(12) C5 0.0372(10) 0.0481(11) 0.0595(13) 0.0007(9) -0.0030(9) 0.0028(9) C6 0.0428(11) 0.0559(12) 0.0615(14) 0.0136(10) 0.0044(9) 0.0085(10) C7 0.0490(16) 0.0640(19) 0.0537(17) 0.000 0.000 0.0179(15) C8 0.145(3) 0.091(2) 0.0706(17) 0.0137(14) 0.0408(17) 0.030(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 F1 C5 1.346(2) . ? F2 C6 1.351(2) . ? N1 C2 1.328(2) . ? N1 C1 1.349(2) . ? N2 C1 1.338(4) . ? N2 H2N 0.90(3) . ? N3 C7 1.379(4) . ? N3 C8 1.437(3) 14 ? N3 C8 1.437(3) . ? C1 N1 1.349(2) 14 ? C2 C3 1.385(2) . ? C2 H2A 0.9300 . ? C3 C2 1.385(2) 14 ? C3 C4 1.482(4) . ? C4 C5 1.388(2) 14 ? C4 C5 1.388(2) . ? C5 C6 1.369(3) . ? C6 C7 1.393(3) . ? C7 C6 1.393(3) 14 ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 N1 C1 116.29(17) . . ? C1 N2 H2N 119.6(15) . . ? C7 N3 C8 121.19(16) . 14 ? C7 N3 C8 121.20(16) . . ? C8 N3 C8 117.6(3) 14 . ? N2 C1 N1 117.60(12) . 14 ? N2 C1 N1 117.60(12) . . ? N1 C1 N1 124.8(2) 14 . ? N1 C2 C3 124.07(18) . . ? N1 C2 H2A 118.0 . . ? C3 C2 H2A 118.0 . . ? C2 C3 C2 114.5(2) 14 . ? C2 C3 C4 122.76(12) 14 . ? C2 C3 C4 122.76(12) . . ? C5 C4 C5 114.5(2) 14 . ? C5 C4 C3 122.77(12) 14 . ? C5 C4 C3 122.77(12) . . ? F1 C5 C6 117.55(17) . . ? F1 C5 C4 119.49(17) . . ? C6 C5 C4 122.87(19) . . ? F2 C6 C5 117.57(18) . . ? F2 C6 C7 119.52(18) . . ? C5 C6 C7 122.84(19) . . ? N3 C7 C6 122.93(13) . 14 ? N3 C7 C6 122.94(13) . . ? C6 C7 C6 114.1(3) 14 . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.145 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.034 data_compound8 _database_code_depnum_ccdc_archive 'CCDC 880750' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Ag F7 N4 O2' _chemical_formula_sum 'C14 H10 Ag F7 N4 O2' _chemical_formula_weight 507.13 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 28.875(8) _cell_length_b 6.4421(2) _cell_length_c 20.640(4) _cell_angle_alpha 90.00 _cell_angle_beta 121.264(12) _cell_angle_gamma 90.00 _cell_volume 3281.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 406 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.053 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 1.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7081 _exptl_absorpt_correction_T_max 0.9368 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34803 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3775 _reflns_number_gt 2926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Disorder on two positions of C14, F5, F6, anf F7 (84:16). C-C bond length of the second part was restrained to become resonable. 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^)+(0.0327P)^2^+19.9723P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3775 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0903 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.008 _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 0.529238(12) -0.06376(4) 0.459274(15) 0.01773(10) Uani 1 1 d . . . F1 F 0.37872(9) 0.7480(3) 0.19895(12) 0.0241(5) Uani 1 1 d . . . F2 F 0.30670(9) 0.7204(4) 0.05398(12) 0.0256(5) Uani 1 1 d . . . F3 F 0.37556(9) 0.0554(3) 0.04757(12) 0.0227(5) Uani 1 1 d . . . F4 F 0.44506(9) 0.0789(3) 0.19252(12) 0.0202(5) Uani 1 1 d . . . F5A F 0.68940(13) 0.1451(5) 0.72707(17) 0.0405(10) Uani 0.843(7) 1 d P A 1 F6A F 0.6556(2) -0.1153(10) 0.7543(3) 0.0323(12) Uani 0.843(7) 1 d P A 1 F7A F 0.70359(14) -0.1588(8) 0.70132(18) 0.0440(11) Uani 0.843(7) 1 d P A 1 O1 O 0.60636(11) -0.1546(4) 0.57439(15) 0.0222(6) Uani 1 1 d . A . O2 O 0.58375(12) 0.1188(4) 0.62017(15) 0.0246(6) Uani 1 1 d . A . N1 N 0.50376(12) 0.2529(5) 0.40653(17) 0.0167(7) Uani 1 1 d . . . N2 N 0.56411(14) 0.4408(6) 0.51294(18) 0.0189(7) Uani 1 1 d . . . H2A H 0.5794(17) 0.552(7) 0.532(2) 0.015(10) Uiso 1 1 d . . . H2B H 0.569(2) 0.332(8) 0.537(3) 0.029(13) Uiso 1 1 d . . . N3 N 0.51571(13) 0.6181(5) 0.39948(17) 0.0170(7) Uani 1 1 d . . . N4 N 0.29709(14) 0.3756(6) -0.03289(18) 0.0241(8) Uani 1 1 d . . . C1 C 0.52749(14) 0.4385(6) 0.43866(19) 0.0135(7) Uani 1 1 d . . . C2 C 0.48051(16) 0.6099(6) 0.3244(2) 0.0185(8) Uani 1 1 d . . . H2 H 0.4727 0.7342 0.2958 0.022 Uiso 1 1 calc R . . C3 C 0.45499(15) 0.4277(6) 0.28661(19) 0.0164(7) Uani 1 1 d . . . C4 C 0.46764(15) 0.2527(6) 0.3321(2) 0.0162(8) Uani 1 1 d . . . H4 H 0.4497 0.1263 0.3090 0.019 Uiso 1 1 calc R . . C5 C 0.41575(15) 0.4159(6) 0.2033(2) 0.0166(7) Uani 1 1 d . . . C6 C 0.37973(15) 0.5764(6) 0.1627(2) 0.0183(7) Uani 1 1 d . . . C7 C 0.34219(15) 0.5627(6) 0.0860(2) 0.0188(8) Uani 1 1 d . . . C8 C 0.33693(16) 0.3868(6) 0.0424(2) 0.0203(8) Uani 1 1 d . . . C9 C 0.37324(15) 0.2280(6) 0.0832(2) 0.0167(7) Uani 1 1 d . . . C10 C 0.41073(15) 0.2418(6) 0.1601(2) 0.0181(8) Uani 1 1 d . . . C11 C 0.28963(19) 0.5453(7) -0.0845(2) 0.0305(10) Uani 1 1 d . . . H11A H 0.3126 0.6627 -0.0553 0.046 Uiso 1 1 calc R . . H11B H 0.2516 0.5888 -0.1120 0.046 Uiso 1 1 calc R . . H11C H 0.2997 0.4981 -0.1207 0.046 Uiso 1 1 calc R . . C12 C 0.27527(17) 0.1755(7) -0.0692(2) 0.0270(9) Uani 1 1 d . . . H12A H 0.2972 0.1204 -0.0889 0.041 Uiso 1 1 calc R . . H12B H 0.2378 0.1934 -0.1110 0.041 Uiso 1 1 calc R . . H12C H 0.2762 0.0784 -0.0320 0.041 Uiso 1 1 calc R . . C13 C 0.61356(16) -0.0266(6) 0.6245(2) 0.0198(8) Uani 1 1 d D . . C14A C 0.6663(2) -0.0415(12) 0.7021(3) 0.0233(12) Uani 0.843(7) 1 d P A 1 F5B F 0.6667(7) -0.331(3) 0.7071(10) 0.040(5) Uiso 0.157(7) 1 d P A 2 F6B F 0.6634(13) -0.065(5) 0.760(2) 0.021(7) Uiso 0.157(7) 1 d P A 2 F7B F 0.7076(10) -0.050(4) 0.7136(14) 0.048(7) Uiso 0.157(7) 1 d P A 2 C14B C 0.6596(16) -0.133(7) 0.6979(19) 0.054(16) Uiso 0.157(7) 1 d PD A 2 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 0.02192(16) 0.01399(15) 0.01148(14) 0.00071(12) 0.00458(11) 0.00053(12) F1 0.0281(13) 0.0209(11) 0.0175(11) -0.0007(9) 0.0077(10) 0.0060(10) F2 0.0230(12) 0.0251(12) 0.0184(11) 0.0056(10) 0.0034(10) 0.0057(10) F3 0.0226(12) 0.0261(12) 0.0158(11) -0.0047(10) 0.0074(9) 0.0001(10) F4 0.0215(11) 0.0189(11) 0.0144(10) 0.0000(9) 0.0054(9) 0.0031(9) F5A 0.0306(19) 0.046(2) 0.0250(17) -0.0030(14) 0.0002(14) -0.0167(15) F6A 0.025(2) 0.048(4) 0.0147(19) 0.009(2) 0.0046(17) -0.005(2) F7A 0.0260(19) 0.070(3) 0.0209(17) -0.0072(18) 0.0018(14) 0.0252(19) O1 0.0250(15) 0.0220(14) 0.0143(13) 0.0003(11) 0.0064(12) 0.0007(12) O2 0.0331(17) 0.0232(15) 0.0187(14) 0.0026(11) 0.0141(13) 0.0017(13) N1 0.0153(16) 0.0199(16) 0.0126(15) -0.0005(12) 0.0055(13) -0.0004(13) N2 0.0240(18) 0.0123(16) 0.0130(15) -0.0005(14) 0.0043(14) -0.0013(15) N3 0.0199(16) 0.0156(15) 0.0107(15) 0.0018(12) 0.0046(13) 0.0013(13) N4 0.0209(17) 0.0312(19) 0.0112(15) 0.0011(13) 0.0021(14) -0.0049(15) C1 0.0109(16) 0.0162(17) 0.0106(15) 0.0010(14) 0.0037(14) 0.0028(15) C2 0.023(2) 0.0179(19) 0.0131(18) 0.0037(14) 0.0087(16) 0.0048(15) C3 0.0158(17) 0.0203(18) 0.0112(16) -0.0009(15) 0.0057(14) -0.0006(16) C4 0.0145(18) 0.0189(19) 0.0125(17) -0.0022(14) 0.0051(15) -0.0017(15) C5 0.0176(18) 0.0180(18) 0.0118(16) 0.0018(15) 0.0059(15) -0.0030(16) C6 0.0186(18) 0.0196(18) 0.0139(17) 0.0001(16) 0.0065(15) -0.0017(16) C7 0.0155(18) 0.0219(19) 0.0153(17) 0.0071(16) 0.0053(15) 0.0048(16) C8 0.0174(19) 0.029(2) 0.0116(17) 0.0012(15) 0.0055(15) -0.0041(16) C9 0.0168(18) 0.0188(18) 0.0138(17) -0.0043(15) 0.0074(15) -0.0028(15) C10 0.0163(19) 0.0190(19) 0.0177(18) 0.0043(15) 0.0079(16) 0.0027(15) C11 0.031(2) 0.039(3) 0.0166(19) 0.0053(19) 0.0088(18) 0.002(2) C12 0.025(2) 0.036(2) 0.0156(19) -0.0040(18) 0.0073(18) -0.0057(19) C13 0.0197(19) 0.025(2) 0.0126(17) 0.0004(15) 0.0068(16) -0.0056(17) C14A 0.016(3) 0.040(4) 0.008(2) -0.002(2) 0.0025(18) 0.002(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 Ag1 N1 2.249(3) . ? Ag1 N3 2.319(3) 1_545 ? Ag1 O1 2.336(3) . ? Ag1 Ag1 3.0493(7) 5_656 ? F1 C6 1.344(4) . ? F2 C7 1.348(4) . ? F3 C9 1.354(4) . ? F4 C10 1.357(4) . ? F5A C14A 1.341(8) . ? F6A C14A 1.353(8) . ? F7A C14A 1.322(7) . ? O1 C13 1.252(5) . ? O2 C13 1.244(5) . ? N1 C4 1.337(5) . ? N1 C1 1.366(5) . ? N2 C1 1.336(5) . ? N2 H2A 0.83(5) . ? N2 H2B 0.82(5) . ? N3 C2 1.343(5) . ? N3 C1 1.350(5) . ? N3 Ag1 2.319(3) 1_565 ? N4 C8 1.374(5) . ? N4 C12 1.459(5) . ? N4 C11 1.461(5) . ? C2 C3 1.390(5) . ? C2 H2 0.9500 . ? C3 C4 1.389(5) . ? C3 C5 1.492(5) . ? C4 H4 0.9500 . ? C5 C10 1.393(5) . ? C5 C6 1.396(5) . ? C6 C7 1.382(5) . ? C7 C8 1.405(6) . ? C8 C9 1.392(6) . ? C9 C10 1.383(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14A 1.537(6) . ? C13 C14B 1.562(19) . ? F5B C14B 1.29(5) . ? F6B C14B 1.30(6) . ? F7B C14B 1.36(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 N3 128.45(11) . 1_545 ? N1 Ag1 O1 128.27(10) . . ? N3 Ag1 O1 97.37(10) 1_545 . ? N1 Ag1 Ag1 83.50(8) . 5_656 ? N3 Ag1 Ag1 122.89(8) 1_545 5_656 ? O1 Ag1 Ag1 90.86(7) . 5_656 ? C13 O1 Ag1 109.7(2) . . ? C4 N1 C1 117.0(3) . . ? C4 N1 Ag1 114.8(2) . . ? C1 N1 Ag1 127.1(2) . . ? C1 N2 H2A 118(3) . . ? C1 N2 H2B 118(3) . . ? H2A N2 H2B 124(4) . . ? C2 N3 C1 117.5(3) . . ? C2 N3 Ag1 117.8(2) . 1_565 ? C1 N3 Ag1 121.2(2) . 1_565 ? C8 N4 C12 120.8(3) . . ? C8 N4 C11 120.3(3) . . ? C12 N4 C11 115.2(3) . . ? N2 C1 N3 118.7(3) . . ? N2 C1 N1 117.7(3) . . ? N3 C1 N1 123.5(3) . . ? N3 C2 C3 122.9(3) . . ? N3 C2 H2 118.5 . . ? C3 C2 H2 118.5 . . ? C4 C3 C2 115.4(3) . . ? C4 C3 C5 120.9(3) . . ? C2 C3 C5 123.6(3) . . ? N1 C4 C3 123.4(3) . . ? N1 C4 H4 118.3 . . ? C3 C4 H4 118.3 . . ? C10 C5 C6 114.5(3) . . ? C10 C5 C3 122.9(3) . . ? C6 C5 C3 122.6(3) . . ? F1 C6 C7 117.4(3) . . ? F1 C6 C5 120.0(3) . . ? C7 C6 C5 122.5(3) . . ? F2 C7 C6 117.3(3) . . ? F2 C7 C8 119.5(3) . . ? C6 C7 C8 123.0(3) . . ? N4 C8 C9 124.9(4) . . ? N4 C8 C7 121.0(4) . . ? C9 C8 C7 114.1(3) . . ? F3 C9 C10 116.5(3) . . ? F3 C9 C8 120.6(3) . . ? C10 C9 C8 122.8(3) . . ? F4 C10 C9 116.9(3) . . ? F4 C10 C5 120.0(3) . . ? C9 C10 C5 123.0(3) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 O1 128.7(4) . . ? O2 C13 C14A 113.3(4) . . ? O1 C13 C14A 118.0(4) . . ? O2 C13 C14B 127(2) . . ? O1 C13 C14B 102(2) . . ? C14A C13 C14B 22.8(18) . . ? F7A C14A F5A 105.8(5) . . ? F7A C14A F6A 109.4(6) . . ? F5A C14A F6A 106.3(5) . . ? F7A C14A C13 113.3(4) . . ? F5A C14A C13 111.8(5) . . ? F6A C14A C13 109.9(5) . . ? F5B C14B F6B 105(3) . . ? F5B C14B F7B 107(3) . . ? F6B C14B F7B 94(4) . . ? F5B C14B C13 125(3) . . ? F6B C14B C13 114(3) . . ? F7B C14B C13 108(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.774 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.129 data_compound9 _database_code_depnum_ccdc_archive 'CCDC 880751' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 Ag F4 N4 O, C F3 O3 S' _chemical_formula_sum 'C15 H16 Ag F7 N4 O4 S' _chemical_formula_weight 589.25 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6509(5) _cell_length_b 10.3996(3) _cell_length_c 15.5497(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.8880(19) _cell_angle_gamma 90.00 _cell_volume 2062.42(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 31245 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7503 _exptl_absorpt_correction_T_max 0.9546 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27663 _diffrn_reflns_av_R_equivalents 0.072 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.46 _reflns_number_total 4727 _reflns_number_gt 3637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Hydrogens bonded to N(2) and O(4) were refined isotropically. 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^)+(0.0394P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4727 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.633157(15) 0.259829(17) 0.771501(14) 0.02119(8) Uani 1 1 d . . . S1 S 0.69768(5) 0.16613(6) 0.54776(5) 0.02051(15) Uani 1 1 d . . . F1 F 0.13630(11) 0.43929(15) 0.45738(10) 0.0245(3) Uani 1 1 d . . . F2 F 0.03804(11) 0.38149(15) 0.28196(11) 0.0292(4) Uani 1 1 d . . . F3 F 0.36407(12) 0.28674(16) 0.25259(11) 0.0285(4) Uani 1 1 d . . . F4 F 0.46215(11) 0.35782(14) 0.42406(11) 0.0247(3) Uani 1 1 d . . . F5 F 0.72591(16) -0.08207(16) 0.56466(14) 0.0455(5) Uani 1 1 d . . . F6 F 0.86685(14) 0.0252(2) 0.58417(14) 0.0492(5) Uani 1 1 d . . . F7 F 0.79922(17) 0.02424(19) 0.68992(13) 0.0523(6) Uani 1 1 d . . . O1 O 0.61035(15) 0.15613(18) 0.57891(14) 0.0311(5) Uani 1 1 d . . . O2 O 0.67275(14) 0.14793(17) 0.45010(13) 0.0256(4) Uani 1 1 d . . . O3 O 0.76711(17) 0.27314(18) 0.58626(14) 0.0316(5) Uani 1 1 d . . . O4 O 0.77691(15) 0.36658(18) 0.75643(16) 0.0265(5) Uani 1 1 d . . . H4 H 0.771(3) 0.347(4) 0.704(3) 0.052(12) Uiso 1 1 d . . . N1 N 0.49594(16) 0.38702(19) 0.69214(15) 0.0180(5) Uani 1 1 d . . . N2 N 0.4974(2) 0.5007(2) 0.82037(17) 0.0241(5) Uani 1 1 d . . . H2A H 0.541(2) 0.455(3) 0.854(2) 0.018(8) Uiso 1 1 d . . . H2B H 0.469(3) 0.555(4) 0.851(3) 0.052(11) Uiso 1 1 d . . . N3 N 0.37628(15) 0.55945(19) 0.67996(15) 0.0183(5) Uani 1 1 d . . . N4 N 0.1422(2) 0.2976(3) 0.16848(18) 0.0433(7) Uani 1 1 d . . . C1 C 0.45607(19) 0.4817(2) 0.73003(18) 0.0183(5) Uani 1 1 d . . . C2 C 0.32885(19) 0.5324(2) 0.59088(18) 0.0187(5) Uani 1 1 d . . . H2 H 0.2717 0.5849 0.5555 0.022 Uiso 1 1 calc R . . C3 C 0.35870(19) 0.4313(2) 0.54721(18) 0.0180(5) Uani 1 1 d . . . C4 C 0.44697(19) 0.3638(2) 0.60285(19) 0.0197(6) Uani 1 1 d . . . H4A H 0.4736 0.2974 0.5754 0.024 Uiso 1 1 calc R . . C5 C 0.30414(19) 0.3997(2) 0.44949(18) 0.0176(5) Uani 1 1 d . . . C6 C 0.19500(19) 0.4020(2) 0.40743(18) 0.0180(5) Uani 1 1 d . . . C7 C 0.14343(19) 0.3693(2) 0.3177(2) 0.0223(6) Uani 1 1 d . . . C8 C 0.1966(2) 0.3277(2) 0.26009(19) 0.0235(6) Uani 1 1 d . . . C9 C 0.3045(2) 0.3269(2) 0.30097(19) 0.0210(6) Uani 1 1 d . . . C10 C 0.35642(19) 0.3622(2) 0.39155(19) 0.0194(5) Uani 1 1 d . . . C11 C 0.0602(2) 0.2009(3) 0.1448(2) 0.0342(7) Uani 1 1 d . . . H11A H 0.0832 0.1248 0.1200 0.051 Uiso 1 1 calc R . . H11B H -0.0035 0.2357 0.0984 0.051 Uiso 1 1 calc R . . H11C H 0.0455 0.1771 0.2000 0.051 Uiso 1 1 calc R . . C12 C 0.1810(2) 0.3355(3) 0.0976(2) 0.0308(7) Uani 1 1 d . . . H12A H 0.2287 0.4087 0.1190 0.046 Uiso 1 1 calc R . . H12B H 0.1220 0.3602 0.0422 0.046 Uiso 1 1 calc R . . H12C H 0.2187 0.2634 0.0831 0.046 Uiso 1 1 calc R . . C13 C 0.7768(2) 0.0259(3) 0.5996(2) 0.0316(7) Uani 1 1 d . . . C14 C 0.8834(2) 0.3440(3) 0.8158(2) 0.0323(7) Uani 1 1 d . . . H14A H 0.9136 0.4249 0.8479 0.039 Uiso 1 1 calc R . . H14B H 0.9252 0.3177 0.7782 0.039 Uiso 1 1 calc R . . C15 C 0.8907(2) 0.2420(3) 0.8856(2) 0.0342(7) Uani 1 1 d . . . H15A H 0.8511 0.2688 0.9241 0.051 Uiso 1 1 calc R . . H15B H 0.9644 0.2288 0.9243 0.051 Uiso 1 1 calc R . . H15C H 0.8615 0.1615 0.8541 0.051 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 0.02208(12) 0.01961(12) 0.01926(13) 0.00267(8) 0.00416(9) 0.00113(7) S1 0.0249(3) 0.0200(3) 0.0174(4) 0.0017(3) 0.0086(3) 0.0010(2) F1 0.0200(7) 0.0340(9) 0.0212(9) -0.0032(7) 0.0092(7) 0.0006(6) F2 0.0169(7) 0.0451(10) 0.0224(9) -0.0002(7) 0.0031(7) -0.0029(7) F3 0.0305(9) 0.0367(9) 0.0222(9) -0.0035(7) 0.0144(7) 0.0046(7) F4 0.0190(7) 0.0318(8) 0.0231(9) 0.0017(7) 0.0074(6) 0.0021(6) F5 0.0686(13) 0.0223(9) 0.0476(13) 0.0026(8) 0.0231(10) 0.0068(8) F6 0.0324(10) 0.0651(13) 0.0479(13) -0.0059(10) 0.0115(9) 0.0183(9) F7 0.0745(14) 0.0554(12) 0.0221(11) 0.0126(9) 0.0112(10) 0.0290(10) O1 0.0336(11) 0.0329(11) 0.0336(13) 0.0097(9) 0.0201(10) 0.0081(9) O2 0.0288(10) 0.0295(10) 0.0166(11) 0.0000(8) 0.0057(8) -0.0032(8) O3 0.0432(12) 0.0278(10) 0.0241(12) -0.0034(9) 0.0123(10) -0.0099(9) O4 0.0266(10) 0.0280(11) 0.0246(13) -0.0029(9) 0.0087(9) -0.0054(8) N1 0.0190(11) 0.0175(11) 0.0170(12) 0.0013(9) 0.0057(9) -0.0007(8) N2 0.0279(13) 0.0247(12) 0.0165(14) 0.0010(10) 0.0041(11) 0.0067(10) N3 0.0188(11) 0.0188(11) 0.0165(12) 0.0000(9) 0.0054(9) 0.0003(8) N4 0.0470(16) 0.0679(18) 0.0160(14) -0.0097(13) 0.0124(12) -0.0330(15) C1 0.0175(12) 0.0212(13) 0.0162(14) 0.0011(11) 0.0060(10) -0.0018(10) C2 0.0173(12) 0.0190(12) 0.0199(15) 0.0008(11) 0.0067(11) -0.0015(10) C3 0.0207(13) 0.0173(12) 0.0167(14) 0.0020(10) 0.0077(11) -0.0012(10) C4 0.0202(13) 0.0178(12) 0.0230(16) 0.0016(11) 0.0101(12) -0.0009(10) C5 0.0212(13) 0.0147(12) 0.0161(14) 0.0017(10) 0.0057(11) -0.0005(9) C6 0.0216(13) 0.0149(12) 0.0196(15) -0.0018(10) 0.0099(11) -0.0012(9) C7 0.0179(13) 0.0254(14) 0.0214(16) 0.0036(11) 0.0045(11) -0.0028(10) C8 0.0269(14) 0.0249(14) 0.0187(15) 0.0022(11) 0.0078(12) -0.0042(11) C9 0.0276(14) 0.0205(13) 0.0197(15) 0.0006(11) 0.0146(12) -0.0008(10) C10 0.0187(13) 0.0178(12) 0.0211(15) 0.0016(11) 0.0064(11) 0.0001(10) C11 0.0387(17) 0.0402(17) 0.0225(17) -0.0062(14) 0.0096(14) -0.0086(14) C12 0.0379(17) 0.0357(16) 0.0175(16) -0.0006(12) 0.0083(13) -0.0031(13) C13 0.0379(17) 0.0352(16) 0.0202(16) 0.0008(13) 0.0083(13) 0.0097(13) C14 0.0213(14) 0.0344(16) 0.040(2) -0.0006(14) 0.0097(13) -0.0021(12) C15 0.0260(15) 0.054(2) 0.0222(17) 0.0017(14) 0.0082(13) 0.0048(13) _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 N3 2.236(2) 2_646 ? Ag1 N1 2.266(2) . ? S1 O1 1.442(2) . ? S1 O2 1.445(2) . ? S1 O3 1.446(2) . ? S1 C13 1.823(3) . ? F1 C6 1.356(3) . ? F2 C7 1.351(3) . ? F3 C9 1.355(3) . ? F4 C10 1.349(3) . ? F5 C13 1.331(3) . ? F6 C13 1.333(3) . ? F7 C13 1.327(3) . ? O4 C14 1.436(3) . ? O4 H4 0.82(4) . ? N1 C4 1.331(3) . ? N1 C1 1.357(3) . ? N2 C1 1.329(4) . ? N2 H2A 0.80(3) . ? N2 H2B 0.90(4) . ? N3 C2 1.333(3) . ? N3 C1 1.357(3) . ? N3 Ag1 2.236(2) 2_656 ? N4 C8 1.387(4) . ? N4 C12 1.438(4) . ? N4 C11 1.451(4) . ? C2 C3 1.389(4) . ? C2 H2 0.9500 . ? C3 C4 1.396(3) . ? C3 C5 1.471(4) . ? C4 H4A 0.9500 . ? C5 C10 1.390(4) . ? C5 C6 1.398(4) . ? C6 C7 1.364(4) . ? C7 C8 1.407(4) . ? C8 C9 1.381(4) . ? C9 C10 1.381(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14 C15 1.495(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ag1 N1 126.31(7) 2_646 . ? O1 S1 O2 115.49(12) . . ? O1 S1 O3 114.51(13) . . ? O2 S1 O3 114.20(12) . . ? O1 S1 C13 102.97(13) . . ? O2 S1 C13 103.90(13) . . ? O3 S1 C13 103.59(14) . . ? C14 O4 H4 109(3) . . ? C4 N1 C1 117.0(2) . . ? C4 N1 Ag1 118.20(16) . . ? C1 N1 Ag1 124.67(17) . . ? C1 N2 H2A 123(2) . . ? C1 N2 H2B 123(2) . . ? H2A N2 H2B 112(3) . . ? C2 N3 C1 117.6(2) . . ? C2 N3 Ag1 118.85(16) . 2_656 ? C1 N3 Ag1 119.53(16) . 2_656 ? C8 N4 C12 121.1(2) . . ? C8 N4 C11 119.9(2) . . ? C12 N4 C11 117.2(2) . . ? N2 C1 N1 118.8(2) . . ? N2 C1 N3 118.0(2) . . ? N1 C1 N3 123.2(2) . . ? N3 C2 C3 123.3(2) . . ? N3 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C2 C3 C4 114.6(2) . . ? C2 C3 C5 123.0(2) . . ? C4 C3 C5 122.3(2) . . ? N1 C4 C3 123.8(2) . . ? N1 C4 H4A 118.1 . . ? C3 C4 H4A 118.1 . . ? C10 C5 C6 114.2(2) . . ? C10 C5 C3 123.0(2) . . ? C6 C5 C3 122.8(2) . . ? F1 C6 C7 117.6(2) . . ? F1 C6 C5 119.1(2) . . ? C7 C6 C5 123.4(2) . . ? F2 C7 C6 118.9(2) . . ? F2 C7 C8 118.9(2) . . ? C6 C7 C8 122.2(2) . . ? C9 C8 N4 124.3(3) . . ? C9 C8 C7 114.6(2) . . ? N4 C8 C7 120.9(2) . . ? F3 C9 C8 119.9(2) . . ? F3 C9 C10 117.2(2) . . ? C8 C9 C10 122.9(2) . . ? F4 C10 C9 117.7(2) . . ? F4 C10 C5 119.6(2) . . ? C9 C10 C5 122.7(2) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? F7 C13 F5 108.1(3) . . ? F7 C13 F6 108.1(2) . . ? F5 C13 F6 107.6(2) . . ? F7 C13 S1 110.8(2) . . ? F5 C13 S1 110.7(2) . . ? F6 C13 S1 111.4(2) . . ? O4 C14 C15 111.9(2) . . ? O4 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? O4 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.434 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.093 data_compound10 _database_code_depnum_ccdc_archive 'CCDC 880752' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Ag Cl F4 N4 O4' _chemical_formula_sum 'C12 H10 Ag Cl F4 N4 O4' _chemical_formula_weight 493.56 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.42220(10) _cell_length_b 16.1283(3) _cell_length_c 14.7568(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.4489(13) _cell_angle_gamma 90.00 _cell_volume 1498.08(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15388 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6452 _exptl_absorpt_correction_T_max 0.8826 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32418 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4358 _reflns_number_gt 3330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0337P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4358 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.002 _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 0.51584(3) 0.639004(10) 0.581967(13) 0.01704(7) Uani 1 1 d . . . Cl1 Cl 0.44999(8) 0.56360(3) 0.36349(4) 0.01568(13) Uani 1 1 d . . . F1 F -0.2543(2) 0.92032(8) 0.69264(10) 0.0197(3) Uani 1 1 d . . . F2 F -0.2318(2) 1.08266(8) 0.71148(10) 0.0217(3) Uani 1 1 d . . . F3 F 0.3622(2) 1.08602(8) 0.56435(10) 0.0229(3) Uani 1 1 d . . . F4 F 0.3421(2) 0.92374(8) 0.54852(10) 0.0187(3) Uani 1 1 d . . . O1 O 0.3279(3) 0.57037(11) 0.43656(12) 0.0228(4) Uani 1 1 d . . . O2 O 0.4061(3) 0.48339(10) 0.31957(12) 0.0243(4) Uani 1 1 d . . . O3 O 0.6731(3) 0.56916(11) 0.40435(12) 0.0225(4) Uani 1 1 d . . . O4 O 0.3907(3) 0.62798(10) 0.29709(13) 0.0219(4) Uani 1 1 d . . . N1 N 0.2113(3) 0.69211(11) 0.61105(14) 0.0139(4) Uani 1 1 d . . . N2 N 0.0124(3) 0.57177(13) 0.58628(15) 0.0160(4) Uani 1 1 d . . . H2A H -0.097(4) 0.5481(16) 0.5749(19) 0.017(7) Uiso 1 1 d . . . H2B H 0.128(4) 0.5442(15) 0.5986(17) 0.010(6) Uiso 1 1 d . . . N3 N -0.1683(3) 0.69665(12) 0.58342(14) 0.0141(4) Uani 1 1 d . . . N4 N 0.0845(4) 1.17700(14) 0.6525(2) 0.0503(9) Uani 1 1 d . . . C1 C 0.0179(3) 0.65413(15) 0.59363(16) 0.0136(5) Uani 1 1 d . . . C2 C -0.1574(4) 0.77937(14) 0.58991(16) 0.0146(5) Uani 1 1 d . . . H2 H -0.2865 0.8099 0.5795 0.018 Uiso 1 1 calc R . . C3 C 0.0332(3) 0.82323(14) 0.61115(16) 0.0124(5) Uani 1 1 d . . . C4 C 0.2158(4) 0.77417(14) 0.62229(16) 0.0140(5) Uani 1 1 d . . . H4 H 0.3502 0.8006 0.6387 0.017 Uiso 1 1 calc R . . C5 C 0.0431(3) 0.91440(14) 0.61999(16) 0.0139(5) Uani 1 1 d . . . C6 C -0.1014(3) 0.95999(14) 0.65911(16) 0.0146(5) Uani 1 1 d . . . C7 C -0.0887(4) 1.04489(14) 0.66899(17) 0.0159(5) Uani 1 1 d . . . C8 C 0.0689(4) 1.09242(14) 0.64031(18) 0.0180(5) Uani 1 1 d . . . C9 C 0.2112(4) 1.04624(15) 0.60049(17) 0.0167(5) Uani 1 1 d . . . C10 C 0.2005(4) 0.96153(14) 0.59132(16) 0.0143(5) Uani 1 1 d . . . C11 C -0.0997(4) 1.23009(15) 0.63355(19) 0.0224(6) Uani 1 1 d . . . H11A H -0.2249 1.1973 0.6063 0.034 Uiso 1 1 calc R . . H11B H -0.0775 1.2737 0.5902 0.034 Uiso 1 1 calc R . . H11C H -0.1218 1.2553 0.6913 0.034 Uiso 1 1 calc R . . C12 C 0.2879(4) 1.21800(15) 0.67656(19) 0.0242(6) Uani 1 1 d . . . H12A H 0.3960 1.1780 0.7052 0.036 Uiso 1 1 calc R . . H12B H 0.2790 1.2631 0.7202 0.036 Uiso 1 1 calc R . . H12C H 0.3267 1.2408 0.6206 0.036 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 0.01030(10) 0.01470(10) 0.02675(12) -0.00203(8) 0.00525(7) -0.00063(7) Cl1 0.0154(3) 0.0137(3) 0.0175(3) 0.0003(2) 0.0021(2) 0.0001(2) F1 0.0169(7) 0.0197(7) 0.0254(8) -0.0013(6) 0.0113(6) -0.0005(6) F2 0.0178(7) 0.0191(7) 0.0286(8) -0.0053(6) 0.0058(6) 0.0048(6) F3 0.0181(7) 0.0194(7) 0.0322(9) 0.0064(6) 0.0072(6) -0.0047(6) F4 0.0156(7) 0.0206(7) 0.0224(8) 0.0007(6) 0.0096(6) -0.0009(5) O1 0.0232(10) 0.0293(10) 0.0175(9) -0.0031(8) 0.0082(7) -0.0042(8) O2 0.0360(11) 0.0149(8) 0.0205(10) -0.0033(7) 0.0018(8) 0.0009(8) O3 0.0156(9) 0.0264(10) 0.0234(10) 0.0017(8) -0.0014(7) 0.0025(7) O4 0.0218(9) 0.0160(9) 0.0265(10) 0.0054(7) 0.0016(8) 0.0025(7) N1 0.0112(9) 0.0134(9) 0.0167(10) -0.0002(8) 0.0021(8) -0.0001(7) N2 0.0080(10) 0.0125(10) 0.0272(13) -0.0029(9) 0.0030(9) -0.0011(8) N3 0.0098(9) 0.0136(9) 0.0196(11) -0.0002(8) 0.0041(8) -0.0001(7) N4 0.0164(12) 0.0095(11) 0.119(3) -0.0036(14) -0.0002(14) 0.0008(9) C1 0.0144(11) 0.0151(11) 0.0116(12) -0.0021(9) 0.0033(9) -0.0014(9) C2 0.0123(11) 0.0153(11) 0.0173(12) 0.0015(10) 0.0055(9) 0.0012(9) C3 0.0139(11) 0.0116(11) 0.0118(11) -0.0005(9) 0.0027(9) 0.0007(8) C4 0.0112(11) 0.0166(11) 0.0141(12) -0.0011(9) 0.0024(9) -0.0018(9) C5 0.0122(11) 0.0137(11) 0.0150(12) 0.0001(9) 0.0009(9) -0.0006(9) C6 0.0111(11) 0.0155(12) 0.0164(12) 0.0013(9) 0.0007(9) -0.0013(9) C7 0.0126(11) 0.0154(11) 0.0186(13) -0.0027(10) 0.0005(9) 0.0051(9) C8 0.0136(12) 0.0118(11) 0.0263(14) 0.0002(10) -0.0014(10) 0.0009(9) C9 0.0116(11) 0.0174(12) 0.0198(13) 0.0042(10) -0.0001(9) -0.0029(9) C10 0.0117(11) 0.0160(11) 0.0152(12) -0.0005(9) 0.0031(9) 0.0019(9) C11 0.0293(14) 0.0138(12) 0.0241(14) 0.0019(11) 0.0048(11) 0.0079(10) C12 0.0276(14) 0.0163(12) 0.0286(15) -0.0042(11) 0.0055(11) -0.0061(10) _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 N3 2.2275(19) 1_655 ? Ag1 N1 2.2532(19) . ? Ag1 O2 2.4434(17) 3_666 ? Ag1 O1 2.5017(18) . ? Cl1 O4 1.4266(18) . ? Cl1 O3 1.4426(18) . ? Cl1 O2 1.4494(18) . ? Cl1 O1 1.4579(18) . ? F1 C6 1.346(3) . ? F2 C7 1.356(3) . ? F3 C9 1.357(3) . ? F4 C10 1.351(3) . ? O2 Ag1 2.4435(17) 3_666 ? N1 C4 1.333(3) . ? N1 C1 1.363(3) . ? N2 C1 1.333(3) . ? N2 H2A 0.79(3) . ? N2 H2B 0.85(3) . ? N3 C2 1.338(3) . ? N3 C1 1.361(3) . ? N3 Ag1 2.2275(18) 1_455 ? N4 C8 1.377(3) . ? N4 C11 1.442(3) . ? N4 C12 1.444(3) . ? C2 C3 1.395(3) . ? C2 H2 0.9500 . ? C3 C4 1.397(3) . ? C3 C5 1.476(3) . ? C4 H4 0.9500 . ? C5 C6 1.396(3) . ? C5 C10 1.396(3) . ? C6 C7 1.378(3) . ? C7 C8 1.400(3) . ? C8 C9 1.396(3) . ? C9 C10 1.373(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ag1 N1 131.51(7) 1_655 . ? N3 Ag1 O2 104.62(7) 1_655 3_666 ? N1 Ag1 O2 106.10(7) . 3_666 ? N3 Ag1 O1 118.45(6) 1_655 . ? N1 Ag1 O1 92.42(6) . . ? O2 Ag1 O1 99.19(6) 3_666 . ? O4 Cl1 O3 110.45(11) . . ? O4 Cl1 O2 109.92(11) . . ? O3 Cl1 O2 109.35(11) . . ? O4 Cl1 O1 110.12(11) . . ? O3 Cl1 O1 108.76(10) . . ? O2 Cl1 O1 108.19(11) . . ? Cl1 O1 Ag1 115.38(9) . . ? Cl1 O2 Ag1 117.15(10) . 3_666 ? C4 N1 C1 117.79(19) . . ? C4 N1 Ag1 113.73(15) . . ? C1 N1 Ag1 125.90(15) . . ? C1 N2 H2A 120(2) . . ? C1 N2 H2B 119.6(17) . . ? H2A N2 H2B 120(3) . . ? C2 N3 C1 117.5(2) . . ? C2 N3 Ag1 116.84(15) . 1_455 ? C1 N3 Ag1 124.70(15) . 1_455 ? C8 N4 C11 121.8(2) . . ? C8 N4 C12 121.6(2) . . ? C11 N4 C12 116.3(2) . . ? N2 C1 N3 119.0(2) . . ? N2 C1 N1 118.1(2) . . ? N3 C1 N1 122.8(2) . . ? N3 C2 C3 123.6(2) . . ? N3 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C2 C3 C4 114.7(2) . . ? C2 C3 C5 123.1(2) . . ? C4 C3 C5 122.2(2) . . ? N1 C4 C3 123.4(2) . . ? N1 C4 H4 118.3 . . ? C3 C4 H4 118.3 . . ? C6 C5 C10 114.8(2) . . ? C6 C5 C3 122.7(2) . . ? C10 C5 C3 122.4(2) . . ? F1 C6 C7 117.8(2) . . ? F1 C6 C5 119.7(2) . . ? C7 C6 C5 122.5(2) . . ? F2 C7 C6 117.6(2) . . ? F2 C7 C8 119.4(2) . . ? C6 C7 C8 122.9(2) . . ? N4 C8 C9 123.2(2) . . ? N4 C8 C7 122.8(2) . . ? C9 C8 C7 114.1(2) . . ? F3 C9 C10 117.2(2) . . ? F3 C9 C8 119.5(2) . . ? C10 C9 C8 123.2(2) . . ? F4 C10 C9 118.0(2) . . ? F4 C10 C5 119.4(2) . . ? C9 C10 C5 122.5(2) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.938 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.121 data_compound11a _database_code_depnum_ccdc_archive 'CCDC 880753' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Ag F4 N5 O3' _chemical_formula_sum 'C12 H10 Ag F4 N5 O3' _chemical_formula_weight 456.12 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' 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.32870(10) _cell_length_b 25.1946(8) _cell_length_c 9.1130(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.5912(17) _cell_angle_gamma 90.00 _cell_volume 1428.30(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15430 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.486 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6641 _exptl_absorpt_correction_T_max 0.8656 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17026 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 29.99 _reflns_number_total 4132 _reflns_number_gt 3371 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4132 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.133740(19) 0.335901(6) 0.507394(17) 0.01407(5) Uani 1 1 d . . . F1 F -0.78991(15) 0.47944(5) 0.16218(13) 0.0162(3) Uani 1 1 d . . . F2 F -0.82211(16) 0.56159(5) -0.01808(12) 0.0171(3) Uani 1 1 d . . . F3 F -0.09497(16) 0.60688(5) 0.17635(13) 0.0160(3) Uani 1 1 d . . . F4 F -0.06388(15) 0.52410(5) 0.35118(12) 0.0153(3) Uani 1 1 d . . . O1 O 0.3290(2) 0.27077(6) 0.39764(16) 0.0184(3) Uani 1 1 d . . . O2 O 0.29546(19) 0.20705(6) 0.23543(16) 0.0187(3) Uani 1 1 d . . . O3 O 0.0192(2) 0.25549(7) 0.25785(18) 0.0281(4) Uani 1 1 d . . . N1 N -0.1833(2) 0.37576(7) 0.46706(18) 0.0122(3) Uani 1 1 d . . . N2 N -0.3131(3) 0.32169(8) 0.6353(2) 0.0157(4) Uani 1 1 d . . . H1 H -0.409(4) 0.3097(11) 0.669(3) 0.027(7) Uiso 1 1 d . . . H2 H -0.189(3) 0.3048(10) 0.652(2) 0.017(6) Uiso 1 1 d . . . N3 N -0.5401(2) 0.38617(7) 0.51542(18) 0.0120(3) Uani 1 1 d . . . N4 N -0.4832(3) 0.63005(7) -0.0325(2) 0.0182(4) Uani 1 1 d . . . N5 N 0.2125(2) 0.24448(7) 0.29657(18) 0.0135(3) Uani 1 1 d . . . C1 C -0.3450(3) 0.36142(8) 0.5383(2) 0.0115(4) Uani 1 1 d . . . C2 C -0.5599(3) 0.42986(8) 0.4310(2) 0.0122(4) Uani 1 1 d . . . H2A H -0.6914 0.4489 0.4196 0.015 Uiso 1 1 calc R . . C3 C -0.3999(3) 0.44928(8) 0.3587(2) 0.0112(4) Uani 1 1 d . . . C4 C -0.2145(3) 0.41810(8) 0.3780(2) 0.0122(4) Uani 1 1 d . . . H4 H -0.1044 0.4276 0.3247 0.015 Uiso 1 1 calc R . . C5 C -0.4234(3) 0.49694(8) 0.2640(2) 0.0114(4) Uani 1 1 d . . . C6 C -0.6158(3) 0.51152(8) 0.1706(2) 0.0122(4) Uani 1 1 d . . . C7 C -0.6339(3) 0.55451(8) 0.0781(2) 0.0128(4) Uani 1 1 d . . . C8 C -0.4625(3) 0.58907(8) 0.0691(2) 0.0130(4) Uani 1 1 d . . . C9 C -0.2701(3) 0.57549(8) 0.1664(2) 0.0127(4) Uani 1 1 d . . . C10 C -0.2539(3) 0.53155(8) 0.2568(2) 0.0110(4) Uani 1 1 d . . . C11 C -0.6663(3) 0.66659(9) -0.0465(3) 0.0203(5) Uani 1 1 d . . . H11A H -0.7650 0.6545 0.0179 0.030 Uiso 1 1 calc R . . H11B H -0.7419 0.6673 -0.1505 0.030 Uiso 1 1 calc R . . H11C H -0.6145 0.7023 -0.0163 0.030 Uiso 1 1 calc R . . C12 C -0.3009(3) 0.64947(9) -0.0925(3) 0.0197(5) Uani 1 1 d . . . H12A H -0.2326 0.6787 -0.0304 0.030 Uiso 1 1 calc R . . H12B H -0.3500 0.6621 -0.1948 0.030 Uiso 1 1 calc R . . H12C H -0.1969 0.6207 -0.0929 0.030 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 0.01031(7) 0.01433(9) 0.01784(9) 0.00237(7) 0.00327(5) 0.00211(5) F1 0.0108(4) 0.0168(7) 0.0203(7) 0.0012(5) 0.0007(4) -0.0032(4) F2 0.0124(4) 0.0202(7) 0.0163(6) 0.0022(5) -0.0041(4) 0.0020(4) F3 0.0144(5) 0.0142(6) 0.0193(6) 0.0014(5) 0.0027(4) -0.0047(4) F4 0.0109(4) 0.0166(6) 0.0167(6) 0.0020(5) -0.0025(4) -0.0008(4) O1 0.0197(6) 0.0166(8) 0.0167(8) -0.0064(7) -0.0024(6) 0.0007(6) O2 0.0177(6) 0.0186(8) 0.0204(8) -0.0088(7) 0.0049(6) 0.0017(6) O3 0.0124(6) 0.0228(9) 0.0458(11) -0.0098(8) -0.0029(6) 0.0039(6) N1 0.0108(6) 0.0137(9) 0.0120(9) 0.0016(7) 0.0018(6) 0.0006(6) N2 0.0108(7) 0.0158(9) 0.0206(10) 0.0060(8) 0.0033(7) 0.0004(6) N3 0.0095(6) 0.0134(9) 0.0129(9) -0.0008(7) 0.0016(6) -0.0004(6) N4 0.0220(8) 0.0150(9) 0.0179(10) 0.0065(8) 0.0044(7) 0.0023(7) N5 0.0144(7) 0.0128(9) 0.0131(9) 0.0014(7) 0.0023(6) -0.0014(6) C1 0.0124(7) 0.0102(10) 0.0112(10) 0.0006(8) 0.0004(7) -0.0026(7) C2 0.0113(7) 0.0116(10) 0.0134(10) -0.0048(8) 0.0012(7) 0.0016(7) C3 0.0119(7) 0.0119(10) 0.0095(10) -0.0014(8) 0.0011(7) 0.0001(7) C4 0.0111(7) 0.0131(10) 0.0126(10) -0.0015(8) 0.0024(7) -0.0022(7) C5 0.0122(7) 0.0114(10) 0.0111(10) -0.0003(8) 0.0029(7) 0.0017(7) C6 0.0108(7) 0.0132(10) 0.0127(10) -0.0029(8) 0.0028(7) -0.0010(7) C7 0.0115(7) 0.0138(10) 0.0119(10) -0.0008(8) -0.0011(7) 0.0013(7) C8 0.0155(8) 0.0128(10) 0.0109(10) -0.0022(8) 0.0030(7) 0.0012(7) C9 0.0122(7) 0.0124(10) 0.0140(10) -0.0023(8) 0.0034(7) -0.0029(7) C10 0.0106(7) 0.0120(10) 0.0096(9) -0.0008(8) -0.0001(7) 0.0002(7) C11 0.0215(9) 0.0145(11) 0.0217(12) 0.0024(9) -0.0044(8) 0.0024(8) C12 0.0278(10) 0.0143(11) 0.0175(12) 0.0009(9) 0.0050(9) -0.0048(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 N1 2.2134(15) . ? Ag1 O1 2.3820(14) . ? Ag1 O2 2.3990(14) 4_566 ? Ag1 N3 2.4111(15) 1_655 ? F1 C6 1.357(2) . ? F2 C7 1.3547(19) . ? F3 C9 1.351(2) . ? F4 C10 1.3567(18) . ? O1 N5 1.257(2) . ? O2 N5 1.258(2) . ? O2 Ag1 2.3990(14) 4_565 ? O3 N5 1.2405(19) . ? N1 C4 1.333(3) . ? N1 C1 1.358(2) . ? N2 C1 1.326(3) . ? N2 H1 0.79(2) . ? N2 H2 0.88(2) . ? N3 C2 1.335(3) . ? N3 C1 1.365(2) . ? N3 Ag1 2.4111(15) 1_455 ? N4 C8 1.377(3) . ? N4 C12 1.450(3) . ? N4 C11 1.467(3) . ? C2 C3 1.394(3) . ? C2 H2A 0.9500 . ? C3 C4 1.396(2) . ? C3 C5 1.470(3) . ? C4 H4 0.9500 . ? C5 C10 1.393(3) . ? C5 C6 1.400(2) . ? C6 C7 1.364(3) . ? C7 C8 1.405(3) . ? C8 C9 1.411(2) . ? C9 C10 1.372(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 O1 140.11(5) . . ? N1 Ag1 O2 125.31(5) . 4_566 ? O1 Ag1 O2 83.19(5) . 4_566 ? N1 Ag1 N3 120.77(6) . 1_655 ? O1 Ag1 N3 82.38(5) . 1_655 ? O2 Ag1 N3 89.09(5) 4_566 1_655 ? N5 O1 Ag1 113.01(11) . . ? N5 O2 Ag1 125.13(10) . 4_565 ? C4 N1 C1 117.65(16) . . ? C4 N1 Ag1 119.50(12) . . ? C1 N1 Ag1 122.66(13) . . ? C1 N2 H1 121.2(18) . . ? C1 N2 H2 119.8(15) . . ? H1 N2 H2 118(2) . . ? C2 N3 C1 116.80(16) . . ? C2 N3 Ag1 115.25(11) . 1_455 ? C1 N3 Ag1 120.67(13) . 1_455 ? C8 N4 C12 121.51(16) . . ? C8 N4 C11 120.34(17) . . ? C12 N4 C11 115.23(18) . . ? O3 N5 O2 120.76(16) . . ? O3 N5 O1 120.36(17) . . ? O2 N5 O1 118.88(14) . . ? N2 C1 N1 118.95(16) . . ? N2 C1 N3 117.99(17) . . ? N1 C1 N3 123.06(18) . . ? N3 C2 C3 124.22(16) . . ? N3 C2 H2A 117.9 . . ? C3 C2 H2A 117.9 . . ? C2 C3 C4 114.17(18) . . ? C2 C3 C5 124.08(16) . . ? C4 C3 C5 121.70(17) . . ? N1 C4 C3 123.64(18) . . ? N1 C4 H4 118.2 . . ? C3 C4 H4 118.2 . . ? C10 C5 C6 113.48(18) . . ? C10 C5 C3 122.89(15) . . ? C6 C5 C3 123.62(17) . . ? F1 C6 C7 117.58(15) . . ? F1 C6 C5 118.97(18) . . ? C7 C6 C5 123.26(17) . . ? F2 C7 C6 117.92(16) . . ? F2 C7 C8 118.47(18) . . ? C6 C7 C8 123.39(16) . . ? N4 C8 C7 121.66(16) . . ? N4 C8 C9 124.71(17) . . ? C7 C8 C9 113.53(18) . . ? F3 C9 C10 117.52(15) . . ? F3 C9 C8 120.19(18) . . ? C10 C9 C8 122.27(17) . . ? F4 C10 C9 116.85(16) . . ? F4 C10 C5 118.96(17) . . ? C9 C10 C5 124.04(16) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.564 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.105 data_compound11b _database_code_depnum_ccdc_archive 'CCDC 880754' #TrackingRef 'comp4_5_6_7_NFAP_8_9_10_11a_11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Ag F4 N5 O3' _chemical_formula_sum 'C12 H10 Ag F4 N5 O3' _chemical_formula_weight 456.12 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 7.8308(3) _cell_length_b 31.6394(14) _cell_length_c 12.6258(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.043(3) _cell_angle_gamma 90.00 _cell_volume 3059.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 40920 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.981 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 1.387 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8295 _exptl_absorpt_correction_T_max 0.9596 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 220(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34698 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3478 _reflns_number_gt 2347 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0463P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3478 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 0.26428(3) 0.497196(7) 0.538016(17) 0.04828(12) Uani 1 1 d . . . F1 F 0.0669(2) 0.35251(6) 0.12419(13) 0.0557(5) Uani 1 1 d . . . F2 F 0.0606(3) 0.26960(6) 0.12725(15) 0.0636(5) Uani 1 1 d . . . F3 F 0.5226(3) 0.27051(5) 0.43800(14) 0.0610(5) Uani 1 1 d . . . F4 F 0.5120(2) 0.35325(5) 0.44031(13) 0.0532(4) Uani 1 1 d . . . O1 O -0.0094(4) 0.45889(9) 0.5556(3) 0.1051(11) Uani 1 1 d . . . O2 O 0.1590(5) 0.40836(9) 0.6125(2) 0.0872(9) Uani 1 1 d . . . O3 O -0.1277(5) 0.40275(9) 0.5850(3) 0.1126(12) Uani 1 1 d . . . N1 N 0.2929(3) 0.46795(8) 0.38422(18) 0.0430(6) Uani 1 1 d . . . N2 N 0.3027(4) 0.53157(10) 0.2957(2) 0.0546(8) Uani 1 1 d . . . H2N1 H 0.268(4) 0.5430(10) 0.348(3) 0.051(10) Uiso 1 1 d . . . H2N2 H 0.284(5) 0.5459(14) 0.240(3) 0.075(13) Uiso 1 1 d . . . N3 N 0.2893(3) 0.47003(7) 0.19475(18) 0.0415(6) Uani 1 1 d . . . N4 N 0.2903(4) 0.22185(9) 0.2876(2) 0.0655(9) Uani 1 1 d . . . N5 N 0.0055(5) 0.42202(9) 0.5857(2) 0.0629(8) Uani 1 1 d . . . C1 C 0.2937(4) 0.48941(11) 0.2917(2) 0.0426(7) Uani 1 1 d . . . C2 C 0.2855(4) 0.42780(9) 0.1934(2) 0.0409(7) Uani 1 1 d . . . H2A H 0.2816 0.4140 0.1271 0.049 Uiso 1 1 calc R . . C3 C 0.2869(4) 0.40334(9) 0.2845(2) 0.0406(7) Uani 1 1 d . . . C4 C 0.2875(4) 0.42579(9) 0.3791(2) 0.0426(7) Uani 1 1 d . . . H4 H 0.2840 0.4106 0.4426 0.051 Uiso 1 1 calc R . . C5 C 0.2868(4) 0.35670(9) 0.2827(2) 0.0406(7) Uani 1 1 d . . . C6 C 0.1832(4) 0.33262(10) 0.2036(2) 0.0466(8) Uani 1 1 d . . . C7 C 0.1807(4) 0.28908(11) 0.2042(2) 0.0493(8) Uani 1 1 d . . . C8 C 0.2887(4) 0.26528(11) 0.2841(2) 0.0488(8) Uani 1 1 d . . . C9 C 0.3999(4) 0.28970(10) 0.3615(2) 0.0472(8) Uani 1 1 d . . . C10 C 0.3960(4) 0.33303(9) 0.3624(2) 0.0432(7) Uani 1 1 d . . . C11 C 0.2490(5) 0.19598(12) 0.1912(3) 0.0726(11) Uani 1 1 d . . . H11A H 0.1263 0.1884 0.1772 0.109 Uiso 1 1 calc R . . H11B H 0.3196 0.1705 0.2017 0.109 Uiso 1 1 calc R . . H11C H 0.2732 0.2117 0.1300 0.109 Uiso 1 1 calc R . . C12 C 0.3037(5) 0.19942(11) 0.3894(3) 0.0732(11) Uani 1 1 d . . . H12A H 0.4188 0.1869 0.4105 0.110 Uiso 1 1 calc R . . H12B H 0.2158 0.1774 0.3808 0.110 Uiso 1 1 calc R . . H12C H 0.2853 0.2190 0.4450 0.110 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 0.0719(2) 0.04832(18) 0.02615(14) -0.00669(9) 0.01372(12) 0.00009(11) F1 0.0677(11) 0.0545(11) 0.0405(10) 0.0031(8) 0.0012(9) 0.0063(9) F2 0.0792(13) 0.0549(11) 0.0506(11) -0.0152(9) -0.0006(10) -0.0036(10) F3 0.0856(13) 0.0482(10) 0.0439(11) 0.0103(8) 0.0018(10) 0.0087(10) F4 0.0727(12) 0.0474(10) 0.0345(10) 0.0005(8) 0.0000(8) -0.0045(9) O1 0.0788(19) 0.073(2) 0.161(3) 0.064(2) 0.0211(19) 0.0080(15) O2 0.127(3) 0.0699(18) 0.0609(18) -0.0018(13) 0.0112(17) 0.0367(18) O3 0.167(3) 0.083(2) 0.111(3) -0.0336(19) 0.084(2) -0.058(2) N1 0.0637(17) 0.0402(14) 0.0269(13) -0.0005(10) 0.0131(12) 0.0041(11) N2 0.092(2) 0.0434(17) 0.0315(16) 0.0010(13) 0.0194(16) 0.0026(15) N3 0.0607(16) 0.0416(14) 0.0238(12) 0.0032(10) 0.0124(11) 0.0022(12) N4 0.107(3) 0.0387(16) 0.0510(19) -0.0038(13) 0.0167(18) 0.0013(14) N5 0.098(3) 0.0479(18) 0.0486(18) -0.0028(14) 0.0281(18) -0.0026(18) C1 0.0535(19) 0.0429(18) 0.0321(17) 0.0006(13) 0.0107(14) 0.0034(14) C2 0.0561(18) 0.0422(17) 0.0266(14) -0.0031(12) 0.0139(13) 0.0034(14) C3 0.0534(18) 0.0396(16) 0.0306(15) 0.0026(12) 0.0129(14) 0.0010(13) C4 0.0630(19) 0.0408(17) 0.0267(15) 0.0009(12) 0.0155(14) 0.0027(14) C5 0.0571(18) 0.0379(16) 0.0279(15) -0.0001(12) 0.0117(13) 0.0010(13) C6 0.061(2) 0.0484(19) 0.0304(16) 0.0027(13) 0.0105(15) 0.0067(15) C7 0.064(2) 0.0500(19) 0.0330(18) -0.0083(14) 0.0082(15) -0.0052(16) C8 0.068(2) 0.0437(18) 0.0372(18) 0.0005(14) 0.0171(16) 0.0026(16) C9 0.069(2) 0.0417(17) 0.0314(16) 0.0050(13) 0.0111(15) 0.0031(15) C10 0.061(2) 0.0426(17) 0.0268(15) -0.0014(13) 0.0121(14) -0.0007(14) C11 0.096(3) 0.049(2) 0.070(3) -0.0179(19) 0.013(2) -0.0028(19) C12 0.100(3) 0.045(2) 0.073(3) 0.0113(18) 0.014(2) -0.0057(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 Ag1 N1 2.204(2) . ? Ag1 N3 2.206(2) 6_566 ? Ag1 O1 2.512(3) . ? Ag1 O1 2.516(3) 5_566 ? F1 C6 1.360(3) . ? F2 C7 1.351(4) . ? F3 C9 1.355(4) . ? F4 C10 1.353(3) . ? O1 N5 1.225(3) . ? O1 Ag1 2.516(3) 5_566 ? O2 N5 1.255(4) . ? O3 N5 1.206(4) . ? N1 C4 1.336(4) . ? N1 C1 1.352(4) . ? N2 C1 1.336(4) . ? N2 H2N1 0.85(3) . ? N2 H2N2 0.82(4) . ? N3 C2 1.337(4) . ? N3 C1 1.363(4) . ? N3 Ag1 2.206(2) 6_565 ? N4 C8 1.375(4) . ? N4 C11 1.447(4) . ? N4 C12 1.453(4) . ? C2 C3 1.384(4) . ? C2 H2A 0.9400 . ? C3 C4 1.388(4) . ? C3 C5 1.476(4) . ? C4 H4 0.9400 . ? C5 C6 1.378(4) . ? C5 C10 1.394(4) . ? C6 C7 1.378(5) . ? C7 C8 1.394(4) . ? C8 C9 1.399(4) . ? C9 C10 1.372(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 N3 168.85(9) . 6_566 ? N1 Ag1 O1 96.94(12) . . ? N3 Ag1 O1 93.74(11) 6_566 . ? N1 Ag1 O1 91.97(12) . 5_566 ? N3 Ag1 O1 94.31(12) 6_566 5_566 ? O1 Ag1 O1 72.55(10) . 5_566 ? N5 O1 Ag1 117.4(2) . . ? N5 O1 Ag1 133.3(3) . 5_566 ? Ag1 O1 Ag1 107.45(10) . 5_566 ? C4 N1 C1 117.7(2) . . ? C4 N1 Ag1 117.00(18) . . ? C1 N1 Ag1 124.7(2) . . ? C1 N2 H2N1 116(2) . . ? C1 N2 H2N2 121(3) . . ? H2N1 N2 H2N2 114(4) . . ? C2 N3 C1 117.2(3) . . ? C2 N3 Ag1 117.46(19) . 6_565 ? C1 N3 Ag1 125.1(2) . 6_565 ? C8 N4 C11 122.6(3) . . ? C8 N4 C12 121.0(3) . . ? C11 N4 C12 115.5(3) . . ? O3 N5 O1 117.0(4) . . ? O3 N5 O2 127.3(4) . . ? O1 N5 O2 115.8(3) . . ? N2 C1 N1 118.6(3) . . ? N2 C1 N3 118.3(3) . . ? N1 C1 N3 123.1(3) . . ? N3 C2 C3 123.5(3) . . ? N3 C2 H2A 118.2 . . ? C3 C2 H2A 118.2 . . ? C2 C3 C4 115.2(3) . . ? C2 C3 C5 123.1(3) . . ? C4 C3 C5 121.6(3) . . ? N1 C4 C3 123.2(3) . . ? N1 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C6 C5 C10 113.9(3) . . ? C6 C5 C3 124.2(3) . . ? C10 C5 C3 121.8(3) . . ? F1 C6 C5 118.8(3) . . ? F1 C6 C7 117.3(3) . . ? C5 C6 C7 123.8(3) . . ? F2 C7 C6 117.4(3) . . ? F2 C7 C8 120.0(3) . . ? C6 C7 C8 122.4(3) . . ? N4 C8 C7 124.3(3) . . ? N4 C8 C9 121.9(3) . . ? C7 C8 C9 113.8(3) . . ? F3 C9 C10 117.1(3) . . ? F3 C9 C8 119.8(3) . . ? C10 C9 C8 123.1(3) . . ? F4 C10 C9 117.8(3) . . ? F4 C10 C5 119.3(3) . . ? C9 C10 C5 122.8(3) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.497 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.082 #===END