# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Department of Chemistry, Temple Hall 423, Missouri State University, Springfield, MO 65897, USA. ; _publ_contact_author_email ericbosch@missouristate.edu _publ_contact_author_fax 417-836-5507 _publ_contact_author_phone 417-836-4277 _publ_contact_author_name 'Prof. Eric Bosch' loop_ _publ_author_name 'Eric Bosch' 'Barrett Eichler' 'Amy Brown' 'Julie Matheny' data_bq3agbf4 _database_code_depnum_ccdc_archive 'CCDC 814736' #TrackingRef '- BoschEichlerManuscriptCif.cif' _audit_update_record ; 2011-02-23 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H15 Ag N3, B F4 ' _chemical_formula_sum 'C22 H15 Ag B F4 N3' _chemical_formula_weight 516.05 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' B B 0.0013 0.0007 '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 triclinic _symmetry_space_group_name_H-M P-1 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9915(9) _cell_length_b 11.7916(15) _cell_length_c 13.0707(16) _cell_angle_alpha 69.3670(10) _cell_angle_beta 81.976(2) _cell_angle_gamma 85.836(2) _cell_volume 998.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5212 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 26.92 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 1.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7415 _exptl_absorpt_correction_T_max 0.9014 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.3660 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11270 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0414 _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 -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 26.98 _reflns_number_total 4283 _reflns_number_gt 3816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (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^)+(0.0320P)^2^+0.6393P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4283 _refine_ls_number_parameters 318 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.73403(3) 0.578288(17) 0.535524(16) 0.02242(8) Uani 1 1 d . . . N1 N 0.8047(3) 0.38890(19) 0.60944(18) 0.0193(5) Uani 1 1 d . . . C1 C 0.7881(4) 0.3146(2) 0.5562(2) 0.0190(5) Uani 1 1 d . . . H1 H 0.7676 0.3485 0.4809 0.023 Uiso 1 1 calc R . . N2 N 0.7140(3) -0.23240(19) 0.43947(17) 0.0182(4) Uani 1 1 d . . . C2 C 0.8368(4) 0.3415(2) 0.7182(2) 0.0172(5) Uani 1 1 d . . . N3 N 0.4315(4) 0.5745(2) 0.6744(2) 0.0308(6) Uani 1 1 d . . . C3 C 0.8585(4) 0.4198(3) 0.7753(2) 0.0235(6) Uani 1 1 d . . . H3 H 0.8520 0.5051 0.7388 0.028 Uiso 1 1 calc R . . C4 C 0.8893(4) 0.3731(3) 0.8838(2) 0.0272(6) Uani 1 1 d . . . H4 H 0.9050 0.4266 0.9219 0.033 Uiso 1 1 calc R . . C5 C 0.8979(4) 0.2470(3) 0.9395(2) 0.0277(6) Uani 1 1 d . . . H5 H 0.9179 0.2159 1.0150 0.033 Uiso 1 1 calc R . . C6 C 0.8778(4) 0.1695(3) 0.8857(2) 0.0232(6) Uani 1 1 d . . . H6 H 0.8842 0.0845 0.9240 0.028 Uiso 1 1 calc R . . C7 C 0.8473(4) 0.2139(2) 0.7733(2) 0.0174(5) Uani 1 1 d . . . C8 C 0.8274(4) 0.1374(2) 0.7143(2) 0.0199(5) Uani 1 1 d . . . H8 H 0.8335 0.0519 0.7496 0.024 Uiso 1 1 calc R . . C9 C 0.7991(4) 0.1863(2) 0.6054(2) 0.0189(5) Uani 1 1 d . . . C10 C 0.7773(4) 0.1142(2) 0.5404(2) 0.0225(6) Uani 1 1 d . . . C11 C 0.7570(4) 0.0535(2) 0.4861(2) 0.0216(6) Uani 1 1 d . . . C12 C 0.7311(4) -0.0250(2) 0.4280(2) 0.0193(5) Uani 1 1 d . . . C13 C 0.7356(4) -0.1521(2) 0.4855(2) 0.0191(5) Uani 1 1 d . . . H13 H 0.7552 -0.1805 0.5610 0.023 Uiso 1 1 calc R . . C14 C 0.6844(3) -0.1935(2) 0.3300(2) 0.0166(5) Uani 1 1 d . . . C15 C 0.6627(4) -0.2784(2) 0.2800(2) 0.0204(5) Uani 1 1 d . . . H15 H 0.6668 -0.3626 0.3219 0.025 Uiso 1 1 calc R . . C16 C 0.6358(4) -0.2412(3) 0.1716(2) 0.0232(6) Uani 1 1 d . . . H16 H 0.6220 -0.2995 0.1383 0.028 Uiso 1 1 calc R . . C17 C 0.6282(4) -0.1164(3) 0.1087(2) 0.0235(6) Uani 1 1 d . . . H17 H 0.6113 -0.0913 0.0329 0.028 Uiso 1 1 calc R . . C18 C 0.6450(4) -0.0317(2) 0.1555(2) 0.0224(6) Uani 1 1 d . . . H18 H 0.6362 0.0520 0.1127 0.027 Uiso 1 1 calc R . . C19 C 0.6756(4) -0.0677(2) 0.2679(2) 0.0187(5) Uani 1 1 d . . . C20 C 0.6994(4) 0.0154(2) 0.3193(2) 0.0207(5) Uani 1 1 d . . . H20 H 0.6935 0.1000 0.2790 0.025 Uiso 1 1 calc R . . C21 C 0.3830(4) 0.5820(3) 0.7588(2) 0.0268(6) Uani 1 1 d . . . C22 C 0.3200(5) 0.5914(3) 0.8658(3) 0.0415(8) Uani 1 1 d . . . H22A H 0.1945 0.6344 0.8644 0.062 Uiso 1 1 calc R . . H22B H 0.4150 0.6363 0.8840 0.062 Uiso 1 1 calc R . . H22C H 0.3080 0.5100 0.9215 0.062 Uiso 1 1 calc R . . F1A F 0.810(2) 0.6596(11) 0.9111(11) 0.106(5) Uani 0.525(19) 1 d PD A 1 B1A B 0.7994(6) 0.7524(3) 0.8271(3) 0.0375(9) Uani 0.525(19) 1 d PD A 1 F2A F 0.6315(9) 0.8057(6) 0.7926(12) 0.085(4) Uani 0.525(19) 1 d PD A 1 F3A F 0.917(2) 0.8420(14) 0.8222(13) 0.063(4) Uani 0.525(19) 1 d PD A 1 F4A F 0.880(2) 0.7124(6) 0.7354(6) 0.073(3) Uani 0.525(19) 1 d PD A 1 F1B F 0.943(2) 0.8284(16) 0.8120(16) 0.057(4) Uani 0.475(19) 1 d PD A 2 B1B B 0.7994(6) 0.7524(3) 0.8271(3) 0.0375(9) Uani 0.475(19) 1 d PD A 2 F2B F 0.6288(10) 0.7937(12) 0.8769(17) 0.119(5) Uani 0.475(19) 1 d PD A 2 F3B F 0.8207(17) 0.6458(10) 0.9215(8) 0.043(2) Uani 0.475(19) 1 d PD A 2 F4B F 0.758(2) 0.7207(10) 0.7477(7) 0.079(4) Uani 0.475(19) 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 0.02979(13) 0.01187(11) 0.02296(12) -0.00229(8) -0.00505(8) 0.00043(8) N1 0.0219(12) 0.0150(11) 0.0196(11) -0.0045(9) -0.0018(9) 0.0000(9) C1 0.0202(13) 0.0167(13) 0.0189(13) -0.0037(11) -0.0047(10) 0.0002(10) N2 0.0190(11) 0.0145(10) 0.0199(11) -0.0046(9) -0.0022(8) 0.0005(8) C2 0.0142(12) 0.0157(12) 0.0196(13) -0.0040(10) -0.0015(9) 0.0007(9) N3 0.0297(14) 0.0306(14) 0.0294(14) -0.0078(11) -0.0023(11) 0.0008(11) C3 0.0245(14) 0.0192(13) 0.0258(14) -0.0066(12) -0.0028(11) -0.0012(11) C4 0.0262(15) 0.0323(16) 0.0270(15) -0.0151(13) -0.0021(12) -0.0028(12) C5 0.0258(15) 0.0355(17) 0.0208(14) -0.0079(13) -0.0039(11) -0.0017(12) C6 0.0197(14) 0.0228(14) 0.0229(14) -0.0028(11) -0.0027(10) -0.0002(11) C7 0.0135(12) 0.0170(12) 0.0202(13) -0.0049(10) -0.0014(9) 0.0002(10) C8 0.0158(13) 0.0150(12) 0.0264(14) -0.0050(11) -0.0013(10) 0.0010(10) C9 0.0155(13) 0.0170(13) 0.0250(13) -0.0087(11) -0.0014(10) 0.0002(10) C10 0.0211(14) 0.0186(13) 0.0266(14) -0.0064(12) -0.0025(11) -0.0010(11) C11 0.0204(14) 0.0178(13) 0.0248(14) -0.0054(11) -0.0025(11) -0.0006(10) C12 0.0164(13) 0.0169(13) 0.0256(14) -0.0092(11) -0.0017(10) 0.0008(10) C13 0.0197(13) 0.0176(13) 0.0203(13) -0.0070(11) -0.0028(10) 0.0003(10) C14 0.0135(12) 0.0154(12) 0.0190(12) -0.0034(10) -0.0024(9) -0.0005(9) C15 0.0180(13) 0.0163(13) 0.0259(14) -0.0061(11) -0.0010(10) -0.0026(10) C16 0.0213(14) 0.0241(14) 0.0275(14) -0.0131(12) -0.0018(11) -0.0027(11) C17 0.0234(14) 0.0272(15) 0.0180(13) -0.0046(12) -0.0045(10) -0.0017(11) C18 0.0228(14) 0.0191(13) 0.0197(13) 0.0000(11) -0.0018(10) -0.0009(11) C19 0.0140(12) 0.0163(12) 0.0229(13) -0.0032(11) -0.0023(10) -0.0006(10) C20 0.0216(13) 0.0139(12) 0.0241(14) -0.0037(11) -0.0027(10) 0.0001(10) C21 0.0279(15) 0.0228(14) 0.0267(15) -0.0054(12) -0.0008(12) -0.0021(12) C22 0.049(2) 0.046(2) 0.0317(17) -0.0180(16) 0.0058(15) -0.0108(16) F1A 0.174(12) 0.043(5) 0.079(7) 0.027(4) -0.051(6) -0.048(6) B1A 0.039(2) 0.0228(18) 0.055(2) -0.0128(18) -0.0211(18) 0.0013(15) F2A 0.046(3) 0.047(4) 0.151(9) -0.009(4) -0.045(4) 0.009(2) F3A 0.106(9) 0.020(3) 0.059(7) 0.009(4) -0.051(6) -0.015(4) F4A 0.129(8) 0.037(3) 0.060(3) -0.020(2) -0.020(5) -0.003(4) F1B 0.048(4) 0.058(9) 0.056(5) -0.004(5) -0.007(4) -0.033(5) B1B 0.039(2) 0.0228(18) 0.055(2) -0.0128(18) -0.0211(18) 0.0013(15) F2B 0.057(4) 0.146(8) 0.218(15) -0.144(9) -0.038(6) 0.047(5) F3B 0.076(5) 0.023(4) 0.025(3) 0.000(3) -0.006(3) -0.010(3) F4B 0.121(9) 0.079(6) 0.036(3) -0.002(3) -0.034(5) -0.052(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.146(2) 1_565 ? Ag1 N1 2.149(2) . ? Ag1 N3 2.580(3) . ? N1 C1 1.316(3) . ? N1 C2 1.376(3) . ? C1 C9 1.421(4) . ? N2 C13 1.314(3) . ? N2 C14 1.381(3) . ? N2 Ag1 2.146(2) 1_545 ? C2 C3 1.404(4) . ? C2 C7 1.423(3) . ? N3 C21 1.139(4) . ? C3 C4 1.370(4) . ? C4 C5 1.409(4) . ? C5 C6 1.359(4) . ? C6 C7 1.417(4) . ? C7 C8 1.402(4) . ? C8 C9 1.371(4) . ? C9 C10 1.426(4) . ? C10 C11 1.199(4) . ? C11 C12 1.424(4) . ? C12 C20 1.374(4) . ? C12 C13 1.421(4) . ? C14 C15 1.402(4) . ? C14 C19 1.419(3) . ? C15 C16 1.364(4) . ? C16 C17 1.412(4) . ? C17 C18 1.361(4) . ? C18 C19 1.421(4) . ? C19 C20 1.400(4) . ? C21 C22 1.447(4) . ? F1A B1A 1.254(12) . ? B1A F2A 1.348(6) . ? B1A F3A 1.364(14) . ? B1A F4A 1.466(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ag1 N1 168.63(8) 1_565 . ? N2 Ag1 N3 96.67(8) 1_565 . ? N1 Ag1 N3 94.70(8) . . ? C1 N1 C2 119.1(2) . . ? C1 N1 Ag1 119.65(17) . . ? C2 N1 Ag1 120.37(17) . . ? N1 C1 C9 123.5(2) . . ? C13 N2 C14 119.5(2) . . ? C13 N2 Ag1 118.99(17) . 1_545 ? C14 N2 Ag1 121.45(17) . 1_545 ? N1 C2 C3 119.7(2) . . ? N1 C2 C7 120.5(2) . . ? C3 C2 C7 119.8(2) . . ? C21 N3 Ag1 142.4(2) . . ? C4 C3 C2 120.0(3) . . ? C3 C4 C5 120.8(3) . . ? C6 C5 C4 120.2(3) . . ? C5 C6 C7 120.8(3) . . ? C8 C7 C6 122.8(2) . . ? C8 C7 C2 118.8(2) . . ? C6 C7 C2 118.4(2) . . ? C9 C8 C7 119.8(2) . . ? C8 C9 C1 118.2(2) . . ? C8 C9 C10 122.9(2) . . ? C1 C9 C10 118.8(2) . . ? C11 C10 C9 179.3(3) . . ? C10 C11 C12 176.3(3) . . ? C20 C12 C13 118.1(2) . . ? C20 C12 C11 123.5(2) . . ? C13 C12 C11 118.4(2) . . ? N2 C13 C12 123.2(2) . . ? N2 C14 C15 119.9(2) . . ? N2 C14 C19 120.3(2) . . ? C15 C14 C19 119.8(2) . . ? C16 C15 C14 120.5(2) . . ? C15 C16 C17 120.2(3) . . ? C18 C17 C16 120.6(2) . . ? C17 C18 C19 120.4(2) . . ? C20 C19 C14 118.8(2) . . ? C20 C19 C18 122.8(2) . . ? C14 C19 C18 118.4(2) . . ? C12 C20 C19 120.1(2) . . ? N3 C21 C22 179.6(3) . . ? F1A B1A F2A 123.7(9) . . ? F1A B1A F3A 113.0(10) . . ? F2A B1A F3A 107.4(8) . . ? F1A B1A F4A 104.3(8) . . ? F2A B1A F4A 101.1(5) . . ? F3A B1A F4A 105.2(9) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.646 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.083 #### data_bq3agsbf6 _database_code_depnum_ccdc_archive 'CCDC 814737' #TrackingRef '- BoschEichlerManuscriptCif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H15 Ag N3, F6 Sb' _chemical_formula_sum 'C22 H15 Ag F6 N3 Sb' _chemical_formula_weight 664.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3032(10) _cell_length_b 11.4028(11) _cell_length_c 12.3817(10) _cell_angle_alpha 76.926(2) _cell_angle_beta 83.3280(10) _cell_angle_gamma 72.711(2) _cell_volume 1088.80(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6561 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 26.90 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.028 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 2.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4693 _exptl_absorpt_correction_T_max 0.6961 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.3660 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20615 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4809 _reflns_number_gt 3977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (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^)+(0.0153P)^2^+1.5792P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4809 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0547 _refine_ls_wR_factor_gt 0.0500 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Sb1 Sb -0.21471(3) 0.328789(18) 0.194990(17) 0.02711(6) Uani 1 1 d . . . Ag1 Ag 0.21124(3) 0.04190(2) 0.47611(2) 0.02988(7) Uani 1 1 d . . . F1 F -0.3019(4) 0.4586(2) 0.0799(2) 0.0780(8) Uani 1 1 d . . . N1 N 0.0981(3) 0.1856(2) 0.5720(2) 0.0227(5) Uani 1 1 d . . . C1 C -0.0200(4) 0.2864(3) 0.5293(2) 0.0240(6) Uani 1 1 d . . . H19 H -0.0537 0.2928 0.4569 0.029 Uiso 1 1 calc R . . F2 F -0.1093(3) 0.4293(2) 0.2437(2) 0.0614(7) Uani 1 1 d . . . N2 N -0.6726(3) 0.8738(2) 0.4108(2) 0.0229(5) Uani 1 1 d . . . C2 C 0.1500(4) 0.1755(3) 0.6761(2) 0.0225(6) Uani 1 1 d . . . F3 F -0.0208(3) 0.2691(2) 0.10840(19) 0.0567(6) Uani 1 1 d . . . N3 N 0.3209(4) 0.1922(3) 0.3176(3) 0.0493(8) Uani 1 1 d . . . C3 C 0.2766(4) 0.0683(3) 0.7229(3) 0.0275(7) Uani 1 1 d . . . H12 H 0.3259 0.0037 0.6824 0.033 Uiso 1 1 calc R . . F4 F -0.3161(3) 0.2246(2) 0.14896(19) 0.0503(6) Uani 1 1 d . . . C4 C 0.3280(4) 0.0575(3) 0.8258(3) 0.0345(8) Uani 1 1 d . . . H13 H 0.4139 -0.0146 0.8566 0.041 Uiso 1 1 calc R . . F5 F -0.4080(2) 0.38496(18) 0.28317(18) 0.0460(5) Uani 1 1 d . . . C5 C 0.2555(4) 0.1519(3) 0.8873(3) 0.0361(8) Uani 1 1 d . . . H14 H 0.2925 0.1426 0.9593 0.043 Uiso 1 1 calc R . . F6 F -0.1321(3) 0.1987(2) 0.31569(18) 0.0549(6) Uani 1 1 d . . . C6 C 0.1334(4) 0.2559(3) 0.8448(3) 0.0320(7) Uani 1 1 d . . . H15 H 0.0855 0.3190 0.8871 0.038 Uiso 1 1 calc R . . C7 C 0.0770(4) 0.2709(3) 0.7377(2) 0.0237(6) Uani 1 1 d . . . C8 C -0.0495(4) 0.3767(3) 0.6893(3) 0.0260(7) Uani 1 1 d . . . H17 H -0.1004 0.4419 0.7288 0.031 Uiso 1 1 calc R . . C9 C -0.0995(4) 0.3859(3) 0.5856(3) 0.0239(6) Uani 1 1 d . . . C10 C -0.2277(4) 0.4911(3) 0.5319(3) 0.0259(7) Uani 1 1 d . . . C11 C -0.3344(4) 0.5773(3) 0.4865(3) 0.0273(7) Uani 1 1 d . . . C12 C -0.4602(4) 0.6753(3) 0.4226(3) 0.0245(6) Uani 1 1 d . . . C13 C -0.5572(4) 0.7811(3) 0.4665(2) 0.0240(6) Uani 1 1 d . . . H9 H -0.5380 0.7852 0.5395 0.029 Uiso 1 1 calc R . . C14 C -0.7032(4) 0.8684(3) 0.3052(2) 0.0213(6) Uani 1 1 d . . . C15 C -0.8269(4) 0.9656(3) 0.2452(3) 0.0272(7) Uani 1 1 d . . . H2 H -0.8894 1.0346 0.2776 0.033 Uiso 1 1 calc R . . C16 C -0.8580(4) 0.9617(3) 0.1406(3) 0.0332(7) Uani 1 1 d . . . H3 H -0.9418 1.0284 0.1007 0.040 Uiso 1 1 calc R . . C17 C -0.7676(4) 0.8600(3) 0.0908(3) 0.0359(8) Uani 1 1 d . . . H4 H -0.7905 0.8585 0.0178 0.043 Uiso 1 1 calc R . . C18 C -0.6474(4) 0.7638(3) 0.1474(3) 0.0313(7) Uani 1 1 d . . . H5 H -0.5870 0.6952 0.1137 0.038 Uiso 1 1 calc R . . C19 C -0.6115(4) 0.7652(3) 0.2562(2) 0.0242(6) Uani 1 1 d . . . C20 C -0.4884(4) 0.6692(3) 0.3176(3) 0.0276(7) Uani 1 1 d . . . H7 H -0.4243 0.5996 0.2863 0.033 Uiso 1 1 calc R . . C21 C 0.3116(5) 0.2635(4) 0.2373(3) 0.0395(8) Uani 1 1 d . . . C22 C 0.2999(5) 0.3562(4) 0.1339(3) 0.0473(10) Uani 1 1 d . . . H22A H 0.1808 0.3970 0.1186 0.071 Uiso 1 1 calc R . . H22B H 0.3563 0.3147 0.0730 0.071 Uiso 1 1 calc R . . H22C H 0.3546 0.4193 0.1405 0.071 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 Sb1 0.03085(12) 0.02362(11) 0.02759(12) -0.00800(8) -0.00163(9) -0.00658(8) Ag1 0.03565(14) 0.02205(12) 0.02780(13) -0.01132(9) -0.00245(11) 0.00312(10) F1 0.102(2) 0.0587(16) 0.0556(16) 0.0257(13) -0.0218(15) -0.0165(15) N1 0.0270(13) 0.0179(12) 0.0207(13) -0.0044(10) 0.0014(10) -0.0030(10) C1 0.0279(16) 0.0200(14) 0.0215(15) -0.0048(11) -0.0003(13) -0.0029(12) F2 0.0550(14) 0.0640(15) 0.0858(19) -0.0409(14) 0.0050(13) -0.0316(12) N2 0.0251(13) 0.0181(12) 0.0227(13) -0.0048(10) -0.0002(10) -0.0018(10) C2 0.0236(15) 0.0220(14) 0.0212(15) -0.0023(11) 0.0018(12) -0.0081(12) F3 0.0516(14) 0.0675(15) 0.0579(15) -0.0320(12) 0.0223(12) -0.0218(12) N3 0.065(2) 0.054(2) 0.0354(18) -0.0034(16) 0.0023(16) -0.0318(18) C3 0.0308(17) 0.0206(15) 0.0284(17) -0.0022(12) -0.0032(14) -0.0045(12) F4 0.0519(13) 0.0560(13) 0.0599(14) -0.0358(11) 0.0034(11) -0.0251(11) C4 0.0355(18) 0.0285(17) 0.0350(19) 0.0055(14) -0.0098(15) -0.0085(14) F5 0.0400(11) 0.0378(11) 0.0610(14) -0.0247(10) 0.0121(10) -0.0069(9) C5 0.043(2) 0.044(2) 0.0240(17) -0.0023(15) -0.0094(15) -0.0170(16) F6 0.0660(15) 0.0436(12) 0.0396(12) -0.0030(10) -0.0121(11) 0.0075(11) C6 0.0406(19) 0.0332(17) 0.0252(17) -0.0096(14) -0.0008(15) -0.0126(15) C7 0.0248(15) 0.0231(15) 0.0243(15) -0.0044(12) 0.0015(13) -0.0095(12) C8 0.0276(16) 0.0210(15) 0.0298(17) -0.0109(12) 0.0041(13) -0.0054(12) C9 0.0217(15) 0.0180(14) 0.0298(17) -0.0050(12) 0.0023(13) -0.0037(11) C10 0.0247(16) 0.0191(14) 0.0317(17) -0.0054(12) 0.0024(13) -0.0043(12) C11 0.0279(16) 0.0211(15) 0.0311(17) -0.0057(13) 0.0038(14) -0.0059(13) C12 0.0223(15) 0.0182(14) 0.0311(17) -0.0020(12) 0.0004(13) -0.0055(11) C13 0.0293(16) 0.0196(14) 0.0209(15) -0.0056(11) 0.0019(13) -0.0037(12) C14 0.0243(15) 0.0201(14) 0.0199(15) -0.0046(11) 0.0020(12) -0.0073(11) C15 0.0294(16) 0.0237(15) 0.0259(16) -0.0044(12) -0.0022(13) -0.0039(13) C16 0.0348(18) 0.0327(18) 0.0303(18) -0.0029(14) -0.0045(15) -0.0080(14) C17 0.043(2) 0.045(2) 0.0243(17) -0.0098(15) -0.0028(15) -0.0158(16) C18 0.0373(18) 0.0315(17) 0.0289(17) -0.0148(14) 0.0049(15) -0.0113(14) C19 0.0263(15) 0.0212(15) 0.0264(16) -0.0076(12) 0.0043(13) -0.0085(12) C20 0.0287(16) 0.0183(15) 0.0338(18) -0.0094(12) 0.0061(14) -0.0033(12) C21 0.040(2) 0.048(2) 0.038(2) -0.0136(17) 0.0063(17) -0.0224(17) C22 0.040(2) 0.059(2) 0.039(2) 0.0065(18) -0.0039(17) -0.0186(18) _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 Sb1 F1 1.843(2) . ? Sb1 F4 1.8596(19) . ? Sb1 F2 1.864(2) . ? Sb1 F5 1.8642(19) . ? Sb1 F3 1.867(2) . ? Sb1 F6 1.880(2) . ? Ag1 N2 2.163(2) 1_645 ? Ag1 N1 2.164(2) . ? Ag1 N3 2.571(3) . ? N1 C1 1.319(4) . ? N1 C2 1.375(4) . ? C1 C9 1.420(4) . ? N2 C13 1.316(4) . ? N2 C14 1.379(4) . ? N2 Ag1 2.163(2) 1_465 ? C2 C3 1.411(4) . ? C2 C7 1.418(4) . ? N3 C21 1.126(4) . ? C3 C4 1.359(4) . ? C4 C5 1.407(5) . ? C5 C6 1.356(5) . ? C6 C7 1.414(4) . ? C7 C8 1.409(4) . ? C8 C9 1.366(4) . ? C9 C10 1.435(4) . ? C10 C11 1.189(4) . ? C11 C12 1.437(4) . ? C12 C20 1.367(4) . ? C12 C13 1.421(4) . ? C14 C15 1.401(4) . ? C14 C19 1.420(4) . ? C15 C16 1.362(4) . ? C16 C17 1.410(5) . ? C17 C18 1.362(5) . ? C18 C19 1.418(4) . ? C19 C20 1.401(4) . ? C21 C22 1.457(5) . ? 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 F1 Sb1 F4 91.22(12) . . ? F1 Sb1 F2 90.36(13) . . ? F4 Sb1 F2 178.36(11) . . ? F1 Sb1 F5 89.29(11) . . ? F4 Sb1 F5 90.05(9) . . ? F2 Sb1 F5 90.38(10) . . ? F1 Sb1 F3 91.77(12) . . ? F4 Sb1 F3 89.33(10) . . ? F2 Sb1 F3 90.21(10) . . ? F5 Sb1 F3 178.78(10) . . ? F1 Sb1 F6 178.01(11) . . ? F4 Sb1 F6 89.00(11) . . ? F2 Sb1 F6 89.43(11) . . ? F5 Sb1 F6 88.73(10) . . ? F3 Sb1 F6 90.21(10) . . ? N2 Ag1 N1 169.01(9) 1_645 . ? N2 Ag1 N3 96.35(10) 1_645 . ? N1 Ag1 N3 93.49(10) . . ? C1 N1 C2 119.1(2) . . ? C1 N1 Ag1 119.7(2) . . ? C2 N1 Ag1 121.23(18) . . ? N1 C1 C9 123.5(3) . . ? C13 N2 C14 119.0(2) . . ? C13 N2 Ag1 120.0(2) . 1_465 ? C14 N2 Ag1 120.49(18) . 1_465 ? N1 C2 C3 119.8(3) . . ? N1 C2 C7 120.9(3) . . ? C3 C2 C7 119.3(3) . . ? C21 N3 Ag1 154.8(3) . . ? C4 C3 C2 120.1(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C5 C4 120.6(3) . . ? C5 C6 C7 120.3(3) . . ? C8 C7 C6 122.9(3) . . ? C8 C7 C2 118.2(3) . . ? C6 C7 C2 118.9(3) . . ? C9 C8 C7 120.4(3) . . ? C8 C9 C1 118.0(3) . . ? C8 C9 C10 123.0(3) . . ? C1 C9 C10 119.0(3) . . ? C11 C10 C9 179.2(4) . . ? C10 C11 C12 174.3(3) . . ? C20 C12 C13 118.4(3) . . ? C20 C12 C11 120.7(3) . . ? C13 C12 C11 120.8(3) . . ? N2 C13 C12 123.1(3) . . ? N2 C14 C15 119.8(3) . . ? N2 C14 C19 120.9(3) . . ? C15 C14 C19 119.2(3) . . ? C16 C15 C14 120.5(3) . . ? C15 C16 C17 120.9(3) . . ? C18 C17 C16 120.0(3) . . ? C17 C18 C19 120.5(3) . . ? C20 C19 C18 122.8(3) . . ? C20 C19 C14 118.3(3) . . ? C18 C19 C14 118.9(3) . . ? C12 C20 C19 120.1(3) . . ? N3 C21 C22 179.7(4) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.559 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.092 #### data_bq3agtfa _database_code_depnum_ccdc_archive 'CCDC 814738' #TrackingRef '- BoschEichlerManuscriptCif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 Ag F3 N2 O2' _chemical_formula_sum 'C22 H12 Ag F3 N2 O2' _chemical_formula_weight 501.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 triclinic _symmetry_space_group_name_H-M P-1 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3343(14) _cell_length_b 10.0902(16) _cell_length_c 11.2321(18) _cell_angle_alpha 106.904(2) _cell_angle_beta 95.690(2) _cell_angle_gamma 106.701(2) _cell_volume 950.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3096 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 25.61 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.752 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7841 _exptl_absorpt_correction_T_max 0.9465 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3660 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10414 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.14 _reflns_number_total 4139 _reflns_number_gt 3305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (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^)+(0.0276P)^2^+0.3136P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4139 _refine_ls_number_parameters 299 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.067 _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 0.05282(2) -0.05075(2) 0.16854(2) 0.05623(10) Uani 1 1 d . . . F1 F 0.0700(11) 0.5134(7) 0.1645(10) 0.111(3) Uani 0.580(16) 1 d PD A 1 O1 O -0.0111(3) 0.1598(2) 0.1309(2) 0.0667(6) Uani 1 1 d . . . N1 N 0.3055(2) 0.0280(2) 0.1796(2) 0.0406(5) Uani 1 1 d . . . C1 C 0.3820(3) 0.1699(3) 0.2219(3) 0.0436(6) Uani 1 1 d . . . H1 H 0.3273 0.2357 0.2494 0.052 Uiso 1 1 calc R . . F2 F 0.2411(10) 0.4747(10) 0.2634(14) 0.146(5) Uani 0.580(16) 1 d PDU A 1 O2 O 0.0960(3) 0.2754(2) 0.0049(2) 0.0710(6) Uani 1 1 d . . . N2 N 0.8959(2) 0.8757(2) 0.2963(2) 0.0383(5) Uani 1 1 d . . . C2 C 0.3841(3) -0.0673(3) 0.1406(2) 0.0376(6) Uani 1 1 d . . . F3 F 0.0051(17) 0.4120(6) 0.2920(11) 0.121(4) Uani 0.580(16) 1 d PDU A 1 C3 C 0.3049(3) -0.2197(3) 0.0966(3) 0.0464(6) Uani 1 1 d . . . H8 H 0.1986 -0.2552 0.0950 0.056 Uiso 1 1 calc R . . C4 C 0.3808(4) -0.3158(3) 0.0567(3) 0.0537(7) Uani 1 1 d . . . H7 H 0.3272 -0.4184 0.0287 0.064 Uiso 1 1 calc R . . C5 C 0.5369(4) -0.2653(4) 0.0563(3) 0.0559(8) Uani 1 1 d . . . H6 H 0.5879 -0.3339 0.0268 0.067 Uiso 1 1 calc R . . C6 C 0.6160(3) -0.1194(3) 0.0977(3) 0.0491(7) Uani 1 1 d . . . H5 H 0.7217 -0.0865 0.0961 0.059 Uiso 1 1 calc R . . C7 C 0.5424(3) -0.0157(3) 0.1431(2) 0.0387(6) Uani 1 1 d . . . C8 C 0.6197(3) 0.1362(3) 0.1887(2) 0.0446(6) Uani 1 1 d . . . H3 H 0.7262 0.1734 0.1916 0.053 Uiso 1 1 calc R . . C9 C 0.5408(3) 0.2305(3) 0.2290(3) 0.0436(6) Uani 1 1 d . . . C10 C 0.6098(3) 0.3877(3) 0.2727(3) 0.0499(7) Uani 1 1 d . . . C11 C 0.6604(3) 0.5169(3) 0.3038(3) 0.0500(7) Uani 1 1 d . . . C12 C 0.7212(3) 0.6736(3) 0.3369(3) 0.0438(6) Uani 1 1 d . . . C13 C 0.8351(3) 0.7350(3) 0.2752(2) 0.0409(6) Uani 1 1 d . . . H20 H 0.8693 0.6697 0.2147 0.049 Uiso 1 1 calc R . . C14 C 0.8481(3) 0.9710(3) 0.3843(2) 0.0382(6) Uani 1 1 d . . . C15 C 0.9114(3) 1.1228(3) 0.4078(3) 0.0461(6) Uani 1 1 d . . . H18 H 0.9880 1.1581 0.3642 0.055 Uiso 1 1 calc R . . C16 C 0.8637(4) 1.2188(3) 0.4923(3) 0.0583(8) Uani 1 1 d . . . H17 H 0.9072 1.3211 0.5073 0.070 Uiso 1 1 calc R . . C17 C 0.7519(4) 1.1696(4) 0.5574(3) 0.0639(9) Uani 1 1 d . . . H16 H 0.7201 1.2385 0.6165 0.077 Uiso 1 1 calc R . . C18 C 0.6878(3) 1.0237(4) 0.5372(3) 0.0564(8) Uani 1 1 d . . . H15 H 0.6116 0.9915 0.5823 0.068 Uiso 1 1 calc R . . C19 C 0.7339(3) 0.9195(3) 0.4492(2) 0.0431(6) Uani 1 1 d . . . C20 C 0.6713(3) 0.7674(3) 0.4235(3) 0.0491(7) Uani 1 1 d . . . H13 H 0.5945 0.7300 0.4661 0.059 Uiso 1 1 calc R . . C21 C 0.0580(3) 0.2676(3) 0.1040(3) 0.0469(7) Uani 1 1 d . A . C22 C 0.0995(5) 0.4146(4) 0.2106(4) 0.0732(10) Uani 1 1 d D . . F3A F 0.021(2) 0.493(2) 0.206(2) 0.201(9) Uani 0.420(16) 1 d PDU A 2 F2A F 0.128(3) 0.3978(9) 0.3282(6) 0.122(6) Uani 0.420(16) 1 d PD A 2 F1A F 0.2437(14) 0.4902(12) 0.2196(12) 0.131(6) Uani 0.420(16) 1 d PDU 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 0.04214(13) 0.03852(13) 0.0856(2) 0.01714(11) 0.03088(12) 0.00742(9) F1 0.157(7) 0.041(3) 0.168(6) 0.047(4) 0.078(5) 0.053(3) O1 0.0754(15) 0.0375(11) 0.0902(16) 0.0241(11) 0.0260(13) 0.0172(11) N1 0.0369(11) 0.0350(11) 0.0513(13) 0.0185(10) 0.0155(10) 0.0075(9) C1 0.0399(14) 0.0358(14) 0.0554(17) 0.0181(12) 0.0132(12) 0.0093(11) F2 0.134(7) 0.108(6) 0.133(9) -0.045(5) -0.049(5) 0.059(6) O2 0.0707(15) 0.0707(15) 0.0627(14) 0.0159(12) 0.0277(12) 0.0123(12) N2 0.0319(11) 0.0343(11) 0.0456(12) 0.0140(10) 0.0071(9) 0.0059(9) C2 0.0365(13) 0.0406(14) 0.0387(14) 0.0188(12) 0.0119(11) 0.0101(11) F3 0.172(9) 0.064(3) 0.106(5) 0.000(3) 0.089(6) 0.018(4) C3 0.0451(15) 0.0394(15) 0.0562(17) 0.0204(13) 0.0173(13) 0.0092(12) C4 0.066(2) 0.0415(16) 0.0575(18) 0.0179(14) 0.0184(15) 0.0201(14) C5 0.063(2) 0.063(2) 0.0548(18) 0.0202(15) 0.0182(15) 0.0378(17) C6 0.0403(15) 0.067(2) 0.0467(16) 0.0240(15) 0.0085(12) 0.0234(14) C7 0.0356(13) 0.0475(15) 0.0375(14) 0.0213(12) 0.0083(11) 0.0131(11) C8 0.0309(13) 0.0548(17) 0.0458(16) 0.0239(13) 0.0042(11) 0.0052(12) C9 0.0396(14) 0.0408(14) 0.0462(15) 0.0206(12) 0.0047(12) 0.0022(12) C10 0.0427(15) 0.0467(17) 0.0549(18) 0.0221(14) 0.0057(13) 0.0031(13) C11 0.0430(15) 0.0439(16) 0.0562(18) 0.0209(14) 0.0072(13) 0.0008(13) C12 0.0395(14) 0.0392(14) 0.0478(16) 0.0187(13) 0.0043(12) 0.0031(11) C13 0.0364(13) 0.0368(14) 0.0473(15) 0.0139(12) 0.0078(11) 0.0091(11) C14 0.0346(13) 0.0392(14) 0.0373(14) 0.0120(11) 0.0017(10) 0.0095(11) C15 0.0492(16) 0.0386(14) 0.0423(15) 0.0107(12) 0.0028(12) 0.0074(12) C16 0.070(2) 0.0403(16) 0.0526(18) 0.0051(14) 0.0042(16) 0.0140(15) C17 0.077(2) 0.060(2) 0.0477(18) 0.0012(15) 0.0100(16) 0.0298(18) C18 0.0536(18) 0.069(2) 0.0436(16) 0.0124(15) 0.0148(14) 0.0209(16) C19 0.0384(14) 0.0489(16) 0.0378(14) 0.0131(12) 0.0048(11) 0.0109(12) C20 0.0399(15) 0.0550(17) 0.0488(17) 0.0216(14) 0.0117(12) 0.0051(13) C21 0.0439(15) 0.0379(15) 0.0598(18) 0.0135(13) 0.0171(13) 0.0156(12) C22 0.091(3) 0.0407(19) 0.081(3) 0.0133(18) 0.036(2) 0.012(2) F3A 0.193(16) 0.169(14) 0.205(18) -0.058(11) 0.001(11) 0.143(14) F2A 0.188(14) 0.081(5) 0.048(3) 0.010(3) 0.032(5) -0.019(6) F1A 0.162(11) 0.066(5) 0.076(6) -0.002(4) 0.020(6) -0.064(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.239(2) . ? Ag1 N2 2.274(2) 1_445 ? Ag1 O2 2.439(2) 2 ? Ag1 O1 2.500(2) . ? F1 C22 1.329(8) . ? O1 C21 1.232(3) . ? N1 C1 1.318(3) . ? N1 C2 1.371(3) . ? C1 C9 1.415(4) . ? F2 C22 1.281(8) . ? O2 C21 1.219(3) . ? O2 Ag1 2.439(2) 2 ? N2 C13 1.307(3) . ? N2 C14 1.372(3) . ? N2 Ag1 2.274(2) 1_665 ? C2 C3 1.410(3) . ? C2 C7 1.413(3) . ? F3 C22 1.332(6) . ? C3 C4 1.359(4) . ? C4 C5 1.400(4) . ? C5 C6 1.356(4) . ? C6 C7 1.413(4) . ? C7 C8 1.402(4) . ? C8 C9 1.368(4) . ? C9 C10 1.438(4) . ? C10 C11 1.181(4) . ? C11 C12 1.435(4) . ? C12 C20 1.367(4) . ? C12 C13 1.418(4) . ? C14 C15 1.406(3) . ? C14 C19 1.411(4) . ? C15 C16 1.355(4) . ? C16 C17 1.391(5) . ? C17 C18 1.360(4) . ? C18 C19 1.417(4) . ? C19 C20 1.405(4) . ? C21 C22 1.526(4) . ? C22 F3A 1.230(11) . ? C22 F1A 1.320(11) . ? C22 F2A 1.390(9) . ? 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 N2 135.80(8) . 1_445 ? N1 Ag1 O2 116.80(8) . 2 ? N2 Ag1 O2 88.83(7) 1_445 2 ? N1 Ag1 O1 99.76(7) . . ? N2 Ag1 O1 105.27(7) 1_445 . ? O2 Ag1 O1 108.68(8) 2 . ? C21 O1 Ag1 134.95(19) . . ? C1 N1 C2 118.2(2) . . ? C1 N1 Ag1 119.82(17) . . ? C2 N1 Ag1 121.97(16) . . ? N1 C1 C9 124.0(2) . . ? C21 O2 Ag1 109.35(19) . 2 ? C13 N2 C14 118.4(2) . . ? C13 N2 Ag1 118.40(17) . 1_665 ? C14 N2 Ag1 122.71(16) . 1_665 ? N1 C2 C3 119.2(2) . . ? N1 C2 C7 121.3(2) . . ? C3 C2 C7 119.5(2) . . ? C4 C3 C2 120.0(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C5 C4 120.6(3) . . ? C5 C6 C7 120.5(3) . . ? C8 C7 C2 118.7(2) . . ? C8 C7 C6 122.7(2) . . ? C2 C7 C6 118.6(2) . . ? C9 C8 C7 119.6(2) . . ? C8 C9 C1 118.1(2) . . ? C8 C9 C10 123.2(2) . . ? C1 C9 C10 118.6(3) . . ? C11 C10 C9 176.3(3) . . ? C10 C11 C12 178.0(3) . . ? C20 C12 C13 117.9(2) . . ? C20 C12 C11 122.9(3) . . ? C13 C12 C11 119.2(3) . . ? N2 C13 C12 124.2(2) . . ? N2 C14 C15 119.3(2) . . ? N2 C14 C19 121.3(2) . . ? C15 C14 C19 119.4(2) . . ? C16 C15 C14 120.3(3) . . ? C15 C16 C17 120.8(3) . . ? C18 C17 C16 120.6(3) . . ? C17 C18 C19 120.4(3) . . ? C20 C19 C14 118.5(2) . . ? C20 C19 C18 123.1(3) . . ? C14 C19 C18 118.5(3) . . ? C12 C20 C19 119.7(2) . . ? O2 C21 O1 130.1(3) . . ? O2 C21 C22 115.0(3) . . ? O1 C21 C22 114.9(3) . . ? F3A C22 F2 119.3(10) . . ? F3A C22 F1A 109.3(12) . . ? F2 C22 F1A 24.8(8) . . ? F3A C22 F1 32.4(14) . . ? F2 C22 F1 103.4(7) . . ? F1A C22 F1 84.5(7) . . ? F3A C22 F3 67.4(10) . . ? F2 C22 F3 114.1(7) . . ? F1A C22 F3 134.2(7) . . ? F1 C22 F3 99.6(6) . . ? F3A C22 F2A 113.9(9) . . ? F2 C22 F2A 68.4(7) . . ? F1A C22 F2A 93.1(8) . . ? F1 C22 F2A 138.0(7) . . ? F3 C22 F2A 54.0(5) . . ? F3A C22 C21 118.3(8) . . ? F2 C22 C21 115.6(5) . . ? F1A C22 C21 108.6(6) . . ? F1 C22 C21 109.8(5) . . ? F3 C22 C21 112.5(4) . . ? F2A C22 C21 110.6(5) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.289 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.057 #### data_bq3agpfp _database_code_depnum_ccdc_archive 'CCDC 814739' #TrackingRef '- BoschEichlerManuscriptCif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H12 Ag F5 N2 O2' _chemical_formula_sum 'C23 H12 Ag F5 N2 O2' _chemical_formula_weight 551.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.6617(12) _cell_length_b 9.5813(5) _cell_length_c 20.3753(16) _cell_angle_alpha 90.00 _cell_angle_beta 119.6840(10) _cell_angle_gamma 90.00 _cell_volume 4013.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7057 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 26.86 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 1.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6724 _exptl_absorpt_correction_T_max 0.8640 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'omega and phi multi-scanscans' _diffrn_detector_area_resol_mean 8.3660 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25042 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.14 _reflns_number_total 4451 _reflns_number_gt 3683 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+7.0588P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4451 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0663 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.068665(11) 0.14573(2) 0.347047(11) 0.04066(7) Uani 1 1 d . . . F1 F 0.16373(9) 0.38910(19) 0.22463(10) 0.0580(5) Uani 1 1 d . . . O1 O 0.07742(12) 0.2684(3) 0.24859(11) 0.0646(6) Uani 1 1 d . . . N1 N 0.13662(10) 0.2575(2) 0.46080(10) 0.0301(4) Uani 1 1 d . . . C1 C 0.12513(12) 0.2372(2) 0.51732(13) 0.0315(5) Uani 1 1 d . . . H1 H 0.0939 0.1686 0.5111 0.038 Uiso 1 1 calc R . . F2 F 0.09542(8) 0.38137(16) 0.10450(9) 0.0464(4) Uani 1 1 d . . . O2 O 0.01923(10) 0.1999(3) 0.12940(12) 0.0576(6) Uani 1 1 d . . . N2 N 0.07775(9) 0.0774(2) 0.81645(10) 0.0295(4) Uani 1 1 d . . . C2 C 0.18226(11) 0.3559(2) 0.46991(12) 0.0275(5) Uani 1 1 d . . . F3 F 0.18972(10) 0.1130(2) 0.22252(12) 0.0738(6) Uani 1 1 d . . . C3 C 0.19656(12) 0.3768(3) 0.41098(13) 0.0323(5) Uani 1 1 d . . . H3 H 0.1758 0.3211 0.3667 0.039 Uiso 1 1 calc R . . F4 F 0.20880(10) 0.2436(2) 0.15081(13) 0.0740(6) Uani 1 1 d . . . C4 C 0.24009(12) 0.4767(3) 0.41770(15) 0.0395(6) Uani 1 1 d . . . H4 H 0.2497 0.4895 0.3780 0.047 Uiso 1 1 calc R . . F5 F 0.12510(10) 0.1076(2) 0.10268(11) 0.0701(5) Uani 1 1 d . . . C5 C 0.27108(13) 0.5616(3) 0.48273(15) 0.0419(6) Uani 1 1 d . . . H5 H 0.3007 0.6320 0.4862 0.050 Uiso 1 1 calc R . . C6 C 0.25838(12) 0.5425(3) 0.54065(14) 0.0383(6) Uani 1 1 d . . . H6 H 0.2794 0.5997 0.5844 0.046 Uiso 1 1 calc R . . C7 C 0.21421(11) 0.4384(2) 0.53618(13) 0.0288(5) Uani 1 1 d . . . C8 C 0.20030(12) 0.4131(2) 0.59465(13) 0.0313(5) Uani 1 1 d . . . H8 H 0.2213 0.4664 0.6398 0.038 Uiso 1 1 calc R . . C9 C 0.15644(12) 0.3112(2) 0.58654(13) 0.0310(5) Uani 1 1 d . . . C10 C 0.14035(12) 0.2815(3) 0.64442(13) 0.0332(5) Uani 1 1 d . . . C11 C 0.12583(12) 0.2610(3) 0.69177(13) 0.0328(5) Uani 1 1 d . . . C12 C 0.10564(11) 0.2416(2) 0.74714(12) 0.0287(5) Uani 1 1 d . . . C13 C 0.09274(11) 0.3524(2) 0.78055(13) 0.0309(5) Uani 1 1 d . . . H13 H 0.0982 0.4453 0.7684 0.037 Uiso 1 1 calc R . . C14 C 0.07135(11) 0.3276(2) 0.83295(12) 0.0283(5) Uani 1 1 d . . . C15 C 0.05501(12) 0.4368(3) 0.86745(14) 0.0358(5) Uani 1 1 d . . . H15 H 0.0576 0.5311 0.8548 0.043 Uiso 1 1 calc R . . C16 C 0.03563(13) 0.4072(3) 0.91871(14) 0.0406(6) Uani 1 1 d . . . H16 H 0.0252 0.4812 0.9419 0.049 Uiso 1 1 calc R . . C17 C 0.03095(12) 0.2684(3) 0.93750(13) 0.0396(6) Uani 1 1 d . . . H17 H 0.0180 0.2495 0.9739 0.048 Uiso 1 1 calc R . . C18 C 0.04485(12) 0.1602(3) 0.90412(13) 0.0352(5) Uani 1 1 d . . . H18 H 0.0409 0.0666 0.9167 0.042 Uiso 1 1 calc R . . C19 C 0.06521(11) 0.1878(2) 0.85075(12) 0.0281(5) Uani 1 1 d . . . C20 C 0.09657(11) 0.1049(2) 0.76693(13) 0.0307(5) Uani 1 1 d . . . H20 H 0.1046 0.0285 0.7429 0.037 Uiso 1 1 calc R . . C21 C 0.06633(12) 0.2515(3) 0.18356(14) 0.0349(5) Uani 1 1 d . . . C22 C 0.12055(13) 0.3044(3) 0.16807(14) 0.0365(6) Uani 1 1 d . . . C23 C 0.16093(15) 0.1903(3) 0.16018(17) 0.0478(7) 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 0.05905(14) 0.03320(11) 0.04503(12) -0.00962(8) 0.03742(11) -0.00629(9) F1 0.0654(11) 0.0635(11) 0.0545(10) -0.0235(8) 0.0369(9) -0.0245(9) O1 0.0835(16) 0.0854(17) 0.0428(12) -0.0037(11) 0.0448(12) -0.0241(13) N1 0.0374(11) 0.0297(10) 0.0287(10) -0.0013(8) 0.0205(9) 0.0004(8) C1 0.0382(13) 0.0282(12) 0.0356(13) 0.0000(10) 0.0238(11) -0.0039(10) F2 0.0610(10) 0.0428(9) 0.0458(9) 0.0135(7) 0.0344(8) 0.0027(7) O2 0.0473(12) 0.0784(15) 0.0509(12) -0.0076(11) 0.0273(11) -0.0190(11) N2 0.0363(11) 0.0280(10) 0.0288(10) 0.0024(8) 0.0196(9) -0.0003(8) C2 0.0288(11) 0.0290(11) 0.0292(11) 0.0038(9) 0.0177(10) 0.0041(9) F3 0.0674(12) 0.0778(14) 0.0834(14) 0.0388(11) 0.0428(11) 0.0299(10) C3 0.0343(13) 0.0379(13) 0.0282(12) 0.0023(10) 0.0181(10) 0.0042(10) F4 0.0769(13) 0.0675(13) 0.1203(17) 0.0100(12) 0.0814(14) 0.0076(10) C4 0.0391(14) 0.0504(16) 0.0382(14) 0.0079(12) 0.0263(12) 0.0015(12) F5 0.0868(14) 0.0585(11) 0.0738(13) -0.0232(10) 0.0464(12) 0.0003(10) C5 0.0374(14) 0.0471(16) 0.0483(15) 0.0023(12) 0.0265(13) -0.0084(12) C6 0.0361(13) 0.0422(14) 0.0384(14) -0.0056(11) 0.0197(12) -0.0060(11) C7 0.0289(12) 0.0312(12) 0.0299(12) 0.0011(9) 0.0172(10) 0.0031(9) C8 0.0360(13) 0.0332(12) 0.0272(11) -0.0017(9) 0.0175(10) 0.0011(10) C9 0.0367(13) 0.0344(12) 0.0288(12) 0.0019(9) 0.0213(11) 0.0045(10) C10 0.0404(14) 0.0329(13) 0.0322(12) -0.0003(10) 0.0224(11) 0.0001(10) C11 0.0364(13) 0.0346(13) 0.0309(12) -0.0009(10) 0.0194(11) -0.0029(10) C12 0.0312(12) 0.0344(12) 0.0228(11) 0.0017(9) 0.0151(10) -0.0030(10) C13 0.0362(13) 0.0292(12) 0.0286(11) 0.0000(9) 0.0171(10) -0.0048(10) C14 0.0297(12) 0.0294(12) 0.0243(11) -0.0036(9) 0.0123(9) -0.0038(9) C15 0.0407(14) 0.0316(13) 0.0346(13) -0.0068(10) 0.0182(11) -0.0040(11) C16 0.0430(15) 0.0469(15) 0.0367(14) -0.0154(12) 0.0234(12) -0.0033(12) C17 0.0374(14) 0.0593(17) 0.0268(12) -0.0029(11) 0.0195(11) -0.0021(12) C18 0.0371(13) 0.0435(14) 0.0276(12) 0.0047(10) 0.0181(11) -0.0001(11) C19 0.0279(11) 0.0337(12) 0.0213(11) 0.0010(9) 0.0112(9) 0.0000(9) C20 0.0365(13) 0.0311(12) 0.0287(12) 0.0001(9) 0.0193(10) 0.0022(10) C21 0.0399(14) 0.0331(13) 0.0401(14) 0.0048(11) 0.0263(12) 0.0013(11) C22 0.0432(14) 0.0403(14) 0.0303(13) 0.0013(10) 0.0214(11) -0.0029(11) C23 0.0525(17) 0.0500(17) 0.0557(18) 0.0060(14) 0.0381(15) 0.0035(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.2665(19) 6 ? Ag1 N1 2.3266(19) . ? Ag1 O2 2.4112(19) 2 ? Ag1 O1 2.4206(19) . ? F1 C22 1.365(3) . ? O1 C21 1.227(3) . ? N1 C1 1.322(3) . ? N1 C2 1.375(3) . ? C1 C9 1.416(3) . ? F2 C22 1.346(3) . ? O2 C21 1.219(3) . ? O2 Ag1 2.4112(19) 2 ? N2 C20 1.316(3) . ? N2 C19 1.379(3) . ? N2 Ag1 2.2664(19) 6_556 ? C2 C3 1.414(3) . ? C2 C7 1.417(3) . ? F3 C23 1.330(3) . ? C3 C4 1.363(3) . ? F4 C23 1.339(3) . ? C4 C5 1.412(4) . ? F5 C23 1.317(4) . ? C5 C6 1.367(3) . ? C6 C7 1.415(3) . ? C7 C8 1.405(3) . ? C8 C9 1.373(3) . ? C9 C10 1.436(3) . ? C10 C11 1.190(3) . ? C11 C12 1.438(3) . ? C12 C13 1.375(3) . ? C12 C20 1.417(3) . ? C13 C14 1.410(3) . ? C14 C19 1.414(3) . ? C14 C15 1.416(3) . ? C15 C16 1.362(3) . ? C16 C17 1.403(4) . ? C17 C18 1.367(4) . ? C18 C19 1.415(3) . ? C21 C22 1.550(3) . ? C22 C23 1.512(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 N2 Ag1 N1 126.53(7) 6 . ? N2 Ag1 O2 117.80(8) 6 2 ? N1 Ag1 O2 86.64(7) . 2 ? N2 Ag1 O1 99.85(7) 6 . ? N1 Ag1 O1 107.55(7) . . ? O2 Ag1 O1 119.78(8) 2 . ? C21 O1 Ag1 140.4(2) . . ? C1 N1 C2 118.01(19) . . ? C1 N1 Ag1 117.48(16) . . ? C2 N1 Ag1 124.00(14) . . ? N1 C1 C9 124.2(2) . . ? C21 O2 Ag1 113.52(16) . 2 ? C20 N2 C19 118.3(2) . . ? C20 N2 Ag1 120.96(16) . 6_556 ? C19 N2 Ag1 120.71(14) . 6_556 ? N1 C2 C3 119.0(2) . . ? N1 C2 C7 121.57(19) . . ? C3 C2 C7 119.4(2) . . ? C4 C3 C2 120.1(2) . . ? C3 C4 C5 121.0(2) . . ? C6 C5 C4 120.0(2) . . ? C5 C6 C7 120.7(2) . . ? C8 C7 C6 122.9(2) . . ? C8 C7 C2 118.2(2) . . ? C6 C7 C2 118.9(2) . . ? C9 C8 C7 120.1(2) . . ? C8 C9 C1 117.8(2) . . ? C8 C9 C10 122.3(2) . . ? C1 C9 C10 119.9(2) . . ? C11 C10 C9 177.8(3) . . ? C10 C11 C12 177.0(3) . . ? C13 C12 C20 118.1(2) . . ? C13 C12 C11 122.0(2) . . ? C20 C12 C11 119.9(2) . . ? C12 C13 C14 119.7(2) . . ? C13 C14 C19 118.4(2) . . ? C13 C14 C15 122.7(2) . . ? C19 C14 C15 119.0(2) . . ? C16 C15 C14 120.3(2) . . ? C15 C16 C17 120.5(2) . . ? C18 C17 C16 120.8(2) . . ? C17 C18 C19 119.9(2) . . ? N2 C19 C14 121.45(19) . . ? N2 C19 C18 119.1(2) . . ? C14 C19 C18 119.4(2) . . ? N2 C20 C12 124.1(2) . . ? O2 C21 O1 129.9(2) . . ? O2 C21 C22 115.2(2) . . ? O1 C21 C22 114.9(2) . . ? F2 C22 F1 106.0(2) . . ? F2 C22 C23 107.2(2) . . ? F1 C22 C23 105.7(2) . . ? F2 C22 C21 111.1(2) . . ? F1 C22 C21 111.8(2) . . ? C23 C22 C21 114.6(2) . . ? F5 C23 F3 108.3(3) . . ? F5 C23 F4 108.6(2) . . ? F3 C23 F4 106.2(2) . . ? F5 C23 C22 111.5(2) . . ? F3 C23 C22 110.7(2) . . ? F4 C23 C22 111.3(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.506 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.063 #### data_bq3agno3 _database_code_depnum_ccdc_archive 'CCDC 814740' #TrackingRef '- BoschEichlerManuscriptCif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 Ag N3 O3' _chemical_formula_sum 'C20 H12 Ag N3 O3' _chemical_formula_weight 450.20 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' 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 triclinic _symmetry_space_group_name_H-M P-1 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3176(9) _cell_length_b 9.8539(9) _cell_length_c 10.8856(10) _cell_angle_alpha 113.6640(10) _cell_angle_beta 94.6320(10) _cell_angle_gamma 105.5170(10) _cell_volume 861.78(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9905 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6462 _exptl_absorpt_correction_T_max 0.8410 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3660 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16351 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.24 _reflns_number_total 3808 _reflns_number_gt 3587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (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^)+(0.0206P)^2^+0.5635P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3808 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0210 _refine_ls_R_factor_gt 0.0194 _refine_ls_wR_factor_ref 0.0494 _refine_ls_wR_factor_gt 0.0485 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.084241(15) -0.002311(15) 0.187316(15) 0.03201(5) Uani 1 1 d . . . O1 O -0.01835(18) 0.14766(16) 0.07432(16) 0.0443(3) Uani 1 1 d . . . N1 N 0.33605(16) 0.06871(16) 0.20396(14) 0.0234(3) Uani 1 1 d . . . C1 C 0.41791(19) 0.21670(19) 0.24733(17) 0.0253(3) Uani 1 1 d . . . H1 H 0.3697 0.2937 0.2834 0.030 Uiso 1 1 calc R . . O2 O 0.14502(19) 0.35738(18) 0.23267(16) 0.0521(4) Uani 1 1 d . . . N2 N 0.92221(15) 0.93557(16) 0.31008(14) 0.0225(3) Uani 1 1 d . . . C2 C 0.40565(18) -0.04351(19) 0.15358(16) 0.0219(3) Uani 1 1 d . . . O3 O 0.0981(2) 0.3320(2) 0.0256(2) 0.0678(5) Uani 1 1 d . . . N3 N 0.07664(18) 0.28194(17) 0.11169(16) 0.0304(3) Uani 1 1 d . . . C3 C 0.3195(2) -0.20258(19) 0.10873(17) 0.0268(3) Uani 1 1 d . . . H3 H 0.2147 -0.2311 0.1121 0.032 Uiso 1 1 calc R . . C4 C 0.3869(2) -0.3159(2) 0.06028(19) 0.0325(4) Uani 1 1 d . . . H4 H 0.3292 -0.4226 0.0326 0.039 Uiso 1 1 calc R . . C5 C 0.5409(2) -0.2753(2) 0.05124(19) 0.0332(4) Uani 1 1 d . . . H5 H 0.5860 -0.3552 0.0163 0.040 Uiso 1 1 calc R . . C6 C 0.6265(2) -0.1225(2) 0.09205(17) 0.0282(4) Uani 1 1 d . . . H6 H 0.7300 -0.0969 0.0840 0.034 Uiso 1 1 calc R . . C7 C 0.56136(18) -0.00188(19) 0.14642(16) 0.0222(3) Uani 1 1 d . . . C8 C 0.64495(18) 0.1578(2) 0.19149(16) 0.0243(3) Uani 1 1 d . . . H8 H 0.7490 0.1888 0.1861 0.029 Uiso 1 1 calc R . . C9 C 0.57427(19) 0.26817(19) 0.24329(17) 0.0246(3) Uani 1 1 d . . . C10 C 0.6471(2) 0.4324(2) 0.28605(18) 0.0280(4) Uani 1 1 d . . . C11 C 0.69609(19) 0.5696(2) 0.31651(17) 0.0270(3) Uani 1 1 d . . . C12 C 0.75106(18) 0.73266(19) 0.34937(17) 0.0242(3) Uani 1 1 d . . . C13 C 0.86652(18) 0.78788(19) 0.28672(17) 0.0241(3) Uani 1 1 d . . . H13 H 0.9055 0.7142 0.2247 0.029 Uiso 1 1 calc R . . C14 C 0.86887(18) 1.04429(19) 0.40139(16) 0.0219(3) Uani 1 1 d . . . C15 C 0.93133(19) 1.2040(2) 0.43109(17) 0.0263(3) Uani 1 1 d . . . H15 H 1.0087 1.2358 0.3871 0.032 Uiso 1 1 calc R . . C16 C 0.8802(2) 1.3130(2) 0.52328(19) 0.0322(4) Uani 1 1 d . . . H16 H 0.9237 1.4205 0.5437 0.039 Uiso 1 1 calc R . . C17 C 0.7644(2) 1.2683(2) 0.58829(19) 0.0345(4) Uani 1 1 d . . . H17 H 0.7304 1.3455 0.6521 0.041 Uiso 1 1 calc R . . C18 C 0.7009(2) 1.1144(2) 0.55996(18) 0.0309(4) Uani 1 1 d . . . H18 H 0.6216 1.0848 0.6031 0.037 Uiso 1 1 calc R . . C19 C 0.75220(19) 0.99844(19) 0.46688(16) 0.0243(3) Uani 1 1 d . . . C20 C 0.69382(19) 0.8389(2) 0.43800(17) 0.0260(3) Uani 1 1 d . . . H20 H 0.6150 0.8049 0.4798 0.031 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 0.02441(8) 0.02857(8) 0.04331(9) 0.01620(6) 0.01702(6) 0.00566(5) O1 0.0477(9) 0.0288(7) 0.0496(8) 0.0161(6) 0.0040(7) 0.0058(6) N1 0.0219(7) 0.0216(7) 0.0272(7) 0.0118(6) 0.0090(5) 0.0050(5) C1 0.0249(8) 0.0215(8) 0.0297(8) 0.0117(7) 0.0088(7) 0.0063(6) O2 0.0558(10) 0.0402(8) 0.0408(8) 0.0047(7) -0.0005(7) 0.0100(7) N2 0.0178(6) 0.0249(7) 0.0242(7) 0.0128(6) 0.0036(5) 0.0032(5) C2 0.0231(8) 0.0235(8) 0.0214(7) 0.0121(6) 0.0070(6) 0.0071(6) O3 0.0680(12) 0.0806(13) 0.0661(12) 0.0520(11) 0.0222(10) 0.0083(10) N3 0.0298(8) 0.0280(7) 0.0358(8) 0.0131(6) 0.0127(6) 0.0130(6) C3 0.0288(8) 0.0238(8) 0.0274(8) 0.0129(7) 0.0086(7) 0.0045(7) C4 0.0417(10) 0.0234(8) 0.0322(9) 0.0129(7) 0.0066(8) 0.0096(8) C5 0.0417(10) 0.0322(9) 0.0302(9) 0.0128(7) 0.0067(8) 0.0210(8) C6 0.0251(8) 0.0376(9) 0.0260(8) 0.0148(7) 0.0052(7) 0.0150(7) C7 0.0227(8) 0.0275(8) 0.0183(7) 0.0125(6) 0.0032(6) 0.0078(6) C8 0.0193(7) 0.0308(8) 0.0232(8) 0.0149(7) 0.0034(6) 0.0043(6) C9 0.0233(8) 0.0237(8) 0.0243(8) 0.0129(6) 0.0033(6) 0.0004(6) C10 0.0247(8) 0.0287(9) 0.0280(8) 0.0144(7) 0.0045(7) 0.0020(7) C11 0.0232(8) 0.0272(9) 0.0266(8) 0.0130(7) 0.0032(7) 0.0011(7) C12 0.0214(8) 0.0240(8) 0.0240(8) 0.0124(6) 0.0012(6) 0.0007(6) C13 0.0212(8) 0.0245(8) 0.0253(8) 0.0117(7) 0.0035(6) 0.0048(6) C14 0.0189(7) 0.0247(8) 0.0201(7) 0.0111(6) 0.0006(6) 0.0035(6) C15 0.0245(8) 0.0259(8) 0.0271(8) 0.0142(7) 0.0036(7) 0.0026(7) C16 0.0362(10) 0.0242(8) 0.0325(9) 0.0128(7) 0.0051(8) 0.0047(7) C17 0.0407(10) 0.0306(9) 0.0300(9) 0.0097(7) 0.0119(8) 0.0129(8) C18 0.0314(9) 0.0328(9) 0.0273(8) 0.0131(7) 0.0118(7) 0.0074(7) C19 0.0238(8) 0.0266(8) 0.0196(7) 0.0104(6) 0.0034(6) 0.0035(7) C20 0.0225(8) 0.0279(8) 0.0244(8) 0.0137(7) 0.0044(6) 0.0004(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.2199(13) 1_445 ? Ag1 N1 2.2312(14) . ? Ag1 O1 2.5519(16) 2 ? Ag1 O1 2.5760(15) . ? O1 N3 1.258(2) . ? O1 Ag1 2.5520(16) 2 ? N1 C1 1.314(2) . ? N1 C2 1.378(2) . ? C1 C9 1.419(2) . ? O2 N3 1.232(2) . ? N2 C13 1.315(2) . ? N2 C14 1.376(2) . ? N2 Ag1 2.2199(13) 1_665 ? C2 C3 1.410(2) . ? C2 C7 1.416(2) . ? O3 N3 1.229(2) . ? C3 C4 1.369(3) . ? C4 C5 1.406(3) . ? C5 C6 1.366(3) . ? C6 C7 1.418(2) . ? C7 C8 1.410(2) . ? C8 C9 1.373(3) . ? C9 C10 1.433(2) . ? C10 C11 1.196(2) . ? C11 C12 1.429(2) . ? C12 C20 1.372(2) . ? C12 C13 1.422(2) . ? C14 C15 1.411(2) . ? C14 C19 1.419(2) . ? C15 C16 1.368(3) . ? C16 C17 1.406(3) . ? C17 C18 1.364(3) . ? C18 C19 1.415(2) . ? C19 C20 1.409(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 N2 Ag1 N1 137.02(5) 1_445 . ? N2 Ag1 O1 120.72(5) 1_445 2 ? N1 Ag1 O1 94.96(5) . 2 ? N2 Ag1 O1 108.42(5) 1_445 . ? N1 Ag1 O1 107.15(5) . . ? O1 Ag1 O1 67.16(6) 2 . ? N3 O1 Ag1 109.47(11) . 2 ? N3 O1 Ag1 110.38(11) . . ? Ag1 O1 Ag1 112.84(6) 2 . ? C1 N1 C2 118.54(14) . . ? C1 N1 Ag1 120.74(11) . . ? C2 N1 Ag1 120.28(10) . . ? N1 C1 C9 123.72(16) . . ? C13 N2 C14 119.01(14) . . ? C13 N2 Ag1 118.77(11) . 1_665 ? C14 N2 Ag1 122.00(10) . 1_665 ? N1 C2 C3 119.05(15) . . ? N1 C2 C7 121.25(14) . . ? C3 C2 C7 119.70(15) . . ? O3 N3 O2 122.69(18) . . ? O3 N3 O1 118.55(17) . . ? O2 N3 O1 118.76(16) . . ? C4 C3 C2 120.09(17) . . ? C3 C4 C5 120.39(17) . . ? C6 C5 C4 120.80(17) . . ? C5 C6 C7 120.18(17) . . ? C8 C7 C2 118.65(15) . . ? C8 C7 C6 122.52(16) . . ? C2 C7 C6 118.81(15) . . ? C9 C8 C7 119.26(15) . . ? C8 C9 C1 118.56(15) . . ? C8 C9 C10 123.55(16) . . ? C1 C9 C10 117.77(16) . . ? C11 C10 C9 174.24(19) . . ? C10 C11 C12 178.18(19) . . ? C20 C12 C13 118.24(15) . . ? C20 C12 C11 122.15(15) . . ? C13 C12 C11 119.59(16) . . ? N2 C13 C12 123.49(16) . . ? N2 C14 C15 119.64(15) . . ? N2 C14 C19 121.00(14) . . ? C15 C14 C19 119.36(15) . . ? C16 C15 C14 119.90(16) . . ? C15 C16 C17 121.05(17) . . ? C18 C17 C16 120.15(18) . . ? C17 C18 C19 120.55(17) . . ? C20 C19 C18 122.60(16) . . ? C20 C19 C14 118.40(16) . . ? C18 C19 C14 118.99(15) . . ? C12 C20 C19 119.83(15) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.396 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.055 #### data_bq3agotf _database_code_depnum_ccdc_archive 'CCDC 814741' #TrackingRef '- BoschEichlerManuscriptCif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H12 Ag F3 N2 O3 S' _chemical_formula_sum 'C21 H12 Ag F3 N2 O3 S' _chemical_formula_weight 537.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6144(11) _cell_length_b 11.9320(10) _cell_length_c 13.3180(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.7020(10) _cell_angle_gamma 90.00 _cell_volume 1920.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7247 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 25.94 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.859 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6758 _exptl_absorpt_correction_T_max 0.9198 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3660 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35365 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.14 _reflns_number_total 4239 _reflns_number_gt 3321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (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^)+(0.0311P)^2^+2.1249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4239 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.576526(19) 1.097576(18) 0.645602(19) 0.03092(9) Uani 1 1 d . . . S1 S 0.28613(7) 0.78784(6) 0.55073(7) 0.03333(19) Uani 1 1 d . . . F1 F 0.12263(17) 0.7808(2) 0.6348(2) 0.0667(7) Uani 1 1 d . . . O1 O 0.3424(2) 0.8821(2) 0.5215(2) 0.0470(6) Uani 1 1 d . . . N1 N 0.66786(19) 0.94235(19) 0.68627(18) 0.0224(5) Uani 1 1 d . . . C1 C 0.6172(2) 0.8453(2) 0.6714(2) 0.0230(6) Uani 1 1 d . . . H1 H 0.5390 0.8447 0.6428 0.028 Uiso 1 1 calc R . . F2 F 0.09755(17) 0.89752(18) 0.5073(2) 0.0579(6) Uani 1 1 d . . . O2 O 0.34739(19) 0.73274(19) 0.64548(19) 0.0428(6) Uani 1 1 d . . . N2 N 0.48601(19) 0.25362(19) 0.61244(19) 0.0235(5) Uani 1 1 d . . . C2 C 0.7823(2) 0.9445(2) 0.7268(2) 0.0233(6) Uani 1 1 d . . . F3 F 0.21078(18) 0.93639(18) 0.65758(18) 0.0533(6) Uani 1 1 d . . . O3 O 0.2313(2) 0.7147(2) 0.4667(2) 0.0656(8) Uani 1 1 d . . . C3 C 0.8381(3) 1.0483(2) 0.7418(2) 0.0306(7) Uani 1 1 d . . . H3 H 0.7978 1.1162 0.7238 0.037 Uiso 1 1 calc R . . C4 C 0.9505(3) 1.0504(3) 0.7823(3) 0.0367(8) Uani 1 1 d . . . H4 H 0.9881 1.1204 0.7915 0.044 Uiso 1 1 calc R . . C5 C 1.0118(3) 0.9514(3) 0.8108(3) 0.0385(8) Uani 1 1 d . . . H5 H 1.0900 0.9550 0.8391 0.046 Uiso 1 1 calc R . . C6 C 0.9597(2) 0.8502(3) 0.7980(3) 0.0315(7) Uani 1 1 d . . . H6 H 1.0015 0.7835 0.8180 0.038 Uiso 1 1 calc R . . C7 C 0.8433(2) 0.8442(2) 0.7550(2) 0.0244(6) Uani 1 1 d . . . C8 C 0.7860(2) 0.7417(2) 0.7388(2) 0.0248(6) Uani 1 1 d . . . H8 H 0.8252 0.6733 0.7574 0.030 Uiso 1 1 calc R . . C9 C 0.6726(2) 0.7408(2) 0.6958(2) 0.0224(6) Uani 1 1 d . . . C10 C 0.6119(2) 0.6391(2) 0.6751(2) 0.0260(6) Uani 1 1 d . . . C11 C 0.5600(2) 0.5529(2) 0.6539(2) 0.0266(6) Uani 1 1 d . . . C12 C 0.4936(2) 0.4554(2) 0.6249(2) 0.0236(6) Uani 1 1 d . . . C13 C 0.5425(2) 0.3474(2) 0.6365(2) 0.0260(6) Uani 1 1 d . . . H13 H 0.6207 0.3425 0.6632 0.031 Uiso 1 1 calc R . . C14 C 0.3728(2) 0.2600(2) 0.5719(2) 0.0229(6) Uani 1 1 d . . . C15 C 0.3108(3) 0.1601(2) 0.5457(2) 0.0278(6) Uani 1 1 d . . . H15 H 0.3470 0.0894 0.5557 0.033 Uiso 1 1 calc R . . C16 C 0.1982(3) 0.1661(3) 0.5058(2) 0.0330(7) Uani 1 1 d . . . H16 H 0.1564 0.0990 0.4879 0.040 Uiso 1 1 calc R . . C17 C 0.1434(3) 0.2696(3) 0.4908(2) 0.0358(8) Uani 1 1 d . . . H17 H 0.0651 0.2719 0.4634 0.043 Uiso 1 1 calc R . . C18 C 0.2014(2) 0.3667(3) 0.5153(2) 0.0301(7) Uani 1 1 d . . . H18 H 0.1634 0.4365 0.5047 0.036 Uiso 1 1 calc R . . C19 C 0.3178(2) 0.3645(2) 0.5565(2) 0.0250(6) Uani 1 1 d . . . C20 C 0.3810(2) 0.4626(2) 0.5842(2) 0.0256(6) Uani 1 1 d . . . H20 H 0.3457 0.5337 0.5748 0.031 Uiso 1 1 calc R . . C21 C 0.1737(3) 0.8543(3) 0.5893(3) 0.0398(8) 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 0.03631(14) 0.01629(12) 0.03961(16) 0.00305(10) 0.01002(10) 0.00398(9) S1 0.0363(4) 0.0240(4) 0.0370(5) -0.0021(3) 0.0062(3) 0.0010(3) F1 0.0446(12) 0.0587(15) 0.105(2) 0.0344(14) 0.0341(13) -0.0024(11) O1 0.0518(15) 0.0380(14) 0.0621(18) 0.0054(12) 0.0339(13) -0.0002(11) N1 0.0286(13) 0.0178(11) 0.0204(13) 0.0004(9) 0.0065(10) 0.0004(9) C1 0.0273(14) 0.0193(14) 0.0223(16) -0.0011(11) 0.0067(12) -0.0004(11) F2 0.0382(11) 0.0482(13) 0.0769(17) 0.0208(12) -0.0002(11) 0.0091(10) O2 0.0417(13) 0.0361(13) 0.0449(15) 0.0057(11) 0.0031(11) 0.0108(10) N2 0.0291(13) 0.0159(11) 0.0257(14) 0.0004(9) 0.0085(10) -0.0008(9) C2 0.0304(15) 0.0190(13) 0.0212(16) -0.0016(11) 0.0087(12) -0.0013(11) F3 0.0557(13) 0.0464(12) 0.0639(15) -0.0095(11) 0.0271(11) 0.0036(10) O3 0.0748(19) 0.0503(17) 0.0553(19) -0.0217(14) -0.0072(15) 0.0014(15) C3 0.0379(17) 0.0199(14) 0.0336(19) -0.0035(12) 0.0096(14) -0.0025(13) C4 0.0348(17) 0.0307(17) 0.045(2) -0.0095(15) 0.0126(15) -0.0131(14) C5 0.0284(16) 0.0413(19) 0.045(2) -0.0123(16) 0.0094(15) -0.0070(14) C6 0.0296(16) 0.0292(16) 0.0347(19) -0.0062(13) 0.0077(13) 0.0029(13) C7 0.0300(15) 0.0217(14) 0.0214(16) -0.0029(11) 0.0074(12) -0.0013(12) C8 0.0323(15) 0.0175(13) 0.0252(16) -0.0004(11) 0.0092(12) 0.0010(11) C9 0.0305(15) 0.0179(13) 0.0206(16) -0.0002(11) 0.0102(12) -0.0019(11) C10 0.0332(16) 0.0189(14) 0.0269(17) 0.0004(11) 0.0100(13) -0.0004(12) C11 0.0346(16) 0.0214(14) 0.0253(17) 0.0022(11) 0.0110(13) 0.0017(12) C12 0.0335(16) 0.0172(13) 0.0218(16) 0.0007(11) 0.0108(12) -0.0008(11) C13 0.0294(15) 0.0218(15) 0.0270(17) 0.0002(12) 0.0083(12) -0.0021(12) C14 0.0318(15) 0.0185(13) 0.0194(15) 0.0013(11) 0.0088(12) -0.0001(11) C15 0.0410(17) 0.0204(14) 0.0236(17) -0.0006(12) 0.0118(13) -0.0046(12) C16 0.0417(18) 0.0311(17) 0.0259(18) -0.0008(13) 0.0091(14) -0.0146(14) C17 0.0312(16) 0.048(2) 0.0265(18) 0.0009(15) 0.0050(13) -0.0072(15) C18 0.0311(16) 0.0329(16) 0.0251(17) 0.0024(13) 0.0058(13) 0.0018(13) C19 0.0359(16) 0.0205(14) 0.0199(16) 0.0007(11) 0.0098(12) -0.0020(12) C20 0.0378(16) 0.0170(13) 0.0234(16) 0.0030(11) 0.0113(13) 0.0025(12) C21 0.0303(17) 0.0292(17) 0.058(2) 0.0142(16) 0.0090(16) -0.0046(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.162(2) 1_565 ? Ag1 N1 2.166(2) . ? S1 O3 1.431(3) . ? S1 O2 1.436(2) . ? S1 O1 1.443(2) . ? S1 C21 1.823(4) . ? F1 C21 1.332(4) . ? N1 C1 1.310(4) . ? N1 C2 1.388(4) . ? C1 C9 1.421(4) . ? F2 C21 1.333(4) . ? N2 C13 1.316(4) . ? N2 C14 1.376(4) . ? N2 Ag1 2.162(2) 1_545 ? C2 C3 1.411(4) . ? C2 C7 1.414(4) . ? F3 C21 1.327(4) . ? C3 C4 1.365(4) . ? C4 C5 1.403(5) . ? C5 C6 1.362(4) . ? C6 C7 1.416(4) . ? C7 C8 1.406(4) . ? C8 C9 1.379(4) . ? C9 C10 1.419(4) . ? C10 C11 1.208(4) . ? C11 C12 1.421(4) . ? C12 C20 1.369(4) . ? C12 C13 1.418(4) . ? C14 C19 1.412(4) . ? C14 C15 1.413(4) . ? C15 C16 1.368(4) . ? C16 C17 1.402(5) . ? C17 C18 1.360(4) . ? C18 C19 1.412(4) . ? C19 C20 1.405(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 N2 Ag1 N1 177.41(9) 1_565 . ? O3 S1 O2 115.19(16) . . ? O3 S1 O1 115.40(18) . . ? O2 S1 O1 114.34(16) . . ? O3 S1 C21 104.19(18) . . ? O2 S1 C21 102.57(16) . . ? O1 S1 C21 102.71(14) . . ? C1 N1 C2 118.9(2) . . ? C1 N1 Ag1 121.11(19) . . ? C2 N1 Ag1 120.03(18) . . ? N1 C1 C9 123.7(3) . . ? C13 N2 C14 118.5(2) . . ? C13 N2 Ag1 117.74(19) . 1_545 ? C14 N2 Ag1 123.74(18) . 1_545 ? N1 C2 C3 119.5(3) . . ? N1 C2 C7 120.9(2) . . ? C3 C2 C7 119.6(3) . . ? C4 C3 C2 119.5(3) . . ? C3 C4 C5 121.4(3) . . ? C6 C5 C4 120.3(3) . . ? C5 C6 C7 120.2(3) . . ? C8 C7 C2 118.6(3) . . ? C8 C7 C6 122.3(3) . . ? C2 C7 C6 119.2(3) . . ? C9 C8 C7 119.8(3) . . ? C8 C9 C10 121.7(3) . . ? C8 C9 C1 118.1(2) . . ? C10 C9 C1 120.2(3) . . ? C11 C10 C9 177.8(3) . . ? C10 C11 C12 176.4(3) . . ? C20 C12 C13 118.0(3) . . ? C20 C12 C11 121.3(3) . . ? C13 C12 C11 120.7(3) . . ? N2 C13 C12 123.9(3) . . ? N2 C14 C19 121.1(2) . . ? N2 C14 C15 119.2(2) . . ? C19 C14 C15 119.6(3) . . ? C16 C15 C14 119.4(3) . . ? C15 C16 C17 121.0(3) . . ? C18 C17 C16 120.5(3) . . ? C17 C18 C19 120.3(3) . . ? C20 C19 C18 122.3(3) . . ? C20 C19 C14 118.6(3) . . ? C18 C19 C14 119.1(3) . . ? C12 C20 C19 119.8(3) . . ? F3 C21 F1 107.2(3) . . ? F3 C21 F2 107.7(3) . . ? F1 C21 F2 107.4(3) . . ? F3 C21 S1 111.4(2) . . ? F1 C21 S1 111.0(2) . . ? F2 C21 S1 111.9(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.606 _refine_diff_density_min -0.611 _refine_diff_density_rms 0.086