# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Suresh Eringathodi' _publ_contact_author_email sureshe123@rediffmail.com loop_ _publ_author_name 'Kamal Bisht' 'Amal Kathalikkattil' 'Suresh Eringathodi' data_1lcomL1 _database_code_depnum_ccdc_archive 'CCDC 868386' #TrackingRef 'RSCadv-Frev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 N2 O4' _chemical_formula_weight 348.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.6023(9) _cell_length_b 16.038(2) _cell_length_c 9.1681(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.593(3) _cell_angle_gamma 90.00 _cell_volume 816.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1221 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 24.82 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type Multi-SCAN _exptl_absorpt_correction_T_min 0.9507 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4862 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 28.29 _reflns_number_total 1906 _reflns_number_gt 1641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material ? _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^)+(0.0832P)^2^+0.2337P] 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 1906 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.1766 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.247 _refine_ls_restrained_S_all 1.247 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0632(3) 0.07504(9) 0.72696(17) 0.0187(4) Uani 1 d . . . O2 O 1.2830(3) -0.02203(10) 0.85975(18) 0.0214(4) Uani 1 d . . . N1 N 0.6480(4) 0.28044(12) 0.6578(2) 0.0231(5) Uani 1 d . . . C1 C 0.7947(4) 0.21658(15) 0.6986(3) 0.0210(5) Uani 1 d . . . C2 C 0.4579(4) 0.29005(15) 0.7310(3) 0.0216(5) Uani 1 d . . . C3 C 0.4104(4) 0.23830(14) 0.8446(3) 0.0193(5) Uani 1 d . . . C4 C 0.5644(4) 0.17274(14) 0.8852(3) 0.0181(5) Uani 1 d . . . C5 C 0.7619(4) 0.16041(13) 0.8102(2) 0.0162(5) Uani 1 d . . . C6 C 0.9335(4) 0.08984(15) 0.8510(2) 0.0180(5) Uani 1 d . . . C7 C 1.2373(4) 0.01768(13) 0.7479(2) 0.0172(5) Uani 1 d . . . C8 C 1.3703(4) 0.00940(13) 0.6174(2) 0.0165(5) Uani 1 d . . . C9 C 1.5428(4) -0.05304(14) 0.6207(3) 0.0195(5) Uani 1 d . . . C10 C 1.6733(4) -0.06244(14) 0.5030(3) 0.0197(5) Uani 1 d . . . H1 H 0.941(5) 0.2066(17) 0.647(3) 0.029(7) Uiso 1 d . . . H3 H 0.262(5) 0.2467(16) 0.888(3) 0.022(7) Uiso 1 d . . . H2 H 0.351(5) 0.3329(18) 0.699(3) 0.027(7) Uiso 1 d . . . H4 H 0.533(5) 0.1379(18) 0.961(3) 0.034(8) Uiso 1 d . . . H6A H 1.046(4) 0.1041(15) 0.937(3) 0.012(6) Uiso 1 d . . . H6B H 0.843(5) 0.0456(18) 0.864(3) 0.024(7) Uiso 1 d . . . H9 H 1.586(5) -0.0921(19) 0.705(3) 0.031(7) Uiso 1 d . . . H10 H 1.796(4) -0.1084(15) 0.505(3) 0.016(6) Uiso 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 O1 0.0228(9) 0.0189(8) 0.0159(8) 0.0027(6) 0.0082(6) 0.0063(6) O2 0.0297(9) 0.0165(8) 0.0191(9) 0.0044(6) 0.0073(7) 0.0047(7) N1 0.0257(11) 0.0216(10) 0.0231(11) 0.0032(8) 0.0076(8) 0.0025(8) C1 0.0228(12) 0.0218(12) 0.0193(12) 0.0011(9) 0.0061(9) 0.0014(9) C2 0.0261(13) 0.0188(11) 0.0199(12) -0.0002(9) 0.0031(9) 0.0034(10) C3 0.0194(11) 0.0206(12) 0.0188(12) -0.0039(9) 0.0052(9) -0.0009(9) C4 0.0212(12) 0.0190(11) 0.0145(11) 0.0004(9) 0.0036(9) -0.0052(9) C5 0.0180(11) 0.0152(10) 0.0155(11) -0.0023(8) 0.0027(8) -0.0013(9) C6 0.0218(12) 0.0199(11) 0.0138(11) 0.0009(9) 0.0081(9) 0.0011(9) C7 0.0212(11) 0.0129(10) 0.0179(11) -0.0027(8) 0.0036(8) -0.0017(8) C8 0.0183(11) 0.0154(10) 0.0165(11) -0.0028(8) 0.0048(8) -0.0013(9) C9 0.0251(12) 0.0155(11) 0.0184(12) 0.0027(9) 0.0048(9) 0.0006(9) C10 0.0222(12) 0.0172(11) 0.0205(12) 0.0006(9) 0.0058(9) 0.0045(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.336(3) . ? O1 C6 1.448(3) . ? O2 C7 1.206(3) . ? N1 C1 1.335(3) . ? N1 C2 1.341(3) . ? C1 C5 1.394(3) . ? C1 H1 1.01(3) . ? C2 C3 1.384(3) . ? C2 H2 0.93(3) . ? C3 C4 1.380(3) . ? C3 H3 0.98(3) . ? C4 C5 1.392(3) . ? C4 H4 0.93(3) . ? C5 C6 1.500(3) . ? C6 H6A 0.97(2) . ? C6 H6B 0.89(3) . ? C7 C8 1.497(3) . ? C8 C10 1.389(3) 3_856 ? C8 C9 1.389(3) . ? C9 C10 1.389(3) . ? C9 H9 1.00(3) . ? C10 C8 1.389(3) 3_856 ? C10 H10 1.01(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 C7 O1 C6 115.64(17) . . ? C1 N1 C2 116.6(2) . . ? N1 C1 C5 124.5(2) . . ? N1 C1 H1 119.7(16) . . ? C5 C1 H1 115.8(16) . . ? N1 C2 C3 123.5(2) . . ? N1 C2 H2 116.8(17) . . ? C3 C2 H2 119.7(17) . . ? C4 C3 C2 119.0(2) . . ? C4 C3 H3 122.2(16) . . ? C2 C3 H3 118.7(16) . . ? C3 C4 C5 119.0(2) . . ? C3 C4 H4 119.2(18) . . ? C5 C4 H4 121.8(18) . . ? C4 C5 C1 117.5(2) . . ? C4 C5 C6 120.6(2) . . ? C1 C5 C6 121.9(2) . . ? O1 C6 C5 107.42(18) . . ? O1 C6 H6A 109.8(14) . . ? C5 C6 H6A 110.6(14) . . ? O1 C6 H6B 109.3(18) . . ? C5 C6 H6B 106.1(18) . . ? H6A C6 H6B 113(2) . . ? O2 C7 O1 123.7(2) . . ? O2 C7 C8 124.1(2) . . ? O1 C7 C8 112.19(19) . . ? C10 C8 C9 120.5(2) 3_856 . ? C10 C8 C7 121.8(2) 3_856 . ? C9 C8 C7 117.7(2) . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 124.4(17) . . ? C10 C9 H9 115.8(17) . . ? C8 C10 C9 119.7(2) 3_856 . ? C8 C10 H10 120.5(14) 3_856 . ? C9 C10 H10 119.8(14) . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.327 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.074 #===END data_3letmL2 _database_code_depnum_ccdc_archive 'CCDC 868387' #TrackingRef 'RSCadv-Frev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 N2 O4' _chemical_formula_weight 348.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 7.831(3) _cell_length_b 8.838(3) _cell_length_c 12.436(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.886(7) _cell_angle_gamma 90.00 _cell_volume 858.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 628 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 23.54 _exptl_crystal_description Plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9692 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5928 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1508 _reflns_number_gt 926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material ? _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^)+(0.0691P)^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 1508 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.1632 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6665(3) 0.1209(3) -0.01834(15) 0.0695(7) Uani 1 d . . . O2 O 0.6393(3) 0.2097(3) -0.18671(16) 0.0827(9) Uani 1 d . . . N1 N 0.8849(4) -0.2339(4) 0.0123(2) 0.0824(9) Uani 1 d . . . C1 C 0.9447(6) -0.3207(6) 0.0941(4) 0.0944(13) Uani 1 d . . . C2 C 0.9237(5) -0.2908(6) 0.2006(4) 0.0884(12) Uani 1 d . . . C3 C 0.8354(5) -0.1662(5) 0.2254(3) 0.0790(11) Uani 1 d . . . C4 C 0.7727(5) -0.0718(4) 0.1437(3) 0.0691(10) Uani 1 d . . . C5 C 0.8003(4) -0.1099(4) 0.0390(3) 0.0628(9) Uani 1 d . . . C6 C 0.7377(6) -0.0167(4) -0.0563(3) 0.0708(10) Uani 1 d . . . C7 C 0.6254(4) 0.2277(4) -0.0926(2) 0.0615(9) Uani 1 d . . . C8 C 0.5613(4) 0.3665(4) -0.0428(2) 0.0576(8) Uani 1 d . . . C9 C 0.5735(5) 0.3913(5) 0.0676(2) 0.0694(10) Uani 1 d . . . C10 C 0.4865(4) 0.4775(4) -0.1099(2) 0.0687(10) Uani 1 d . . . H1 H 0.995(4) -0.414(4) 0.075(3) 0.092(12) Uiso 1 d . . . H2 H 0.974(4) -0.363(4) 0.253(3) 0.103(13) Uiso 1 d . . . H3 H 0.826(4) -0.140(3) 0.298(3) 0.080(11) Uiso 1 d . . . H4 H 0.721(4) 0.024(4) 0.156(2) 0.076(10) Uiso 1 d . . . H6A H 0.837(4) 0.014(3) -0.096(3) 0.084(11) Uiso 1 d . . . H6B H 0.646(4) -0.071(3) -0.095(2) 0.074(10) Uiso 1 d . . . H9 H 0.630(4) 0.317(4) 0.108(2) 0.081(11) Uiso 1 d . . . H10 H 0.476(4) 0.460(3) -0.187(3) 0.073(9) Uiso 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 O1 0.0899(17) 0.0715(15) 0.0476(12) -0.0011(12) 0.0077(11) 0.0025(13) O2 0.113(2) 0.0991(19) 0.0359(12) -0.0056(12) 0.0062(11) -0.0043(15) N1 0.087(2) 0.081(2) 0.080(2) -0.0084(19) 0.0071(17) 0.0070(18) C1 0.089(3) 0.079(3) 0.116(4) -0.003(3) 0.010(3) 0.015(3) C2 0.084(3) 0.090(3) 0.090(3) 0.015(3) 0.001(2) 0.000(2) C3 0.085(3) 0.086(3) 0.065(3) 0.003(2) 0.003(2) -0.001(2) C4 0.073(2) 0.074(3) 0.059(2) 0.000(2) 0.0033(17) -0.003(2) C5 0.055(2) 0.073(2) 0.061(2) -0.0060(18) 0.0055(15) -0.0111(18) C6 0.076(3) 0.082(3) 0.055(2) -0.0090(19) 0.008(2) -0.007(2) C7 0.061(2) 0.080(2) 0.0433(17) 0.0032(18) 0.0020(14) -0.0155(18) C8 0.064(2) 0.070(2) 0.0385(15) -0.0007(16) 0.0038(14) -0.0145(17) C9 0.091(3) 0.077(3) 0.0385(18) 0.0023(19) -0.0015(16) -0.004(2) C10 0.089(3) 0.085(3) 0.0310(17) 0.0004(18) 0.0001(17) -0.014(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 O1 C7 1.344(3) . ? O1 C6 1.432(4) . ? O2 C7 1.193(3) . ? N1 C1 1.333(5) . ? N1 C5 1.334(4) . ? C1 C2 1.371(6) . ? C1 H1 0.95(4) . ? C2 C3 1.347(5) . ? C2 H2 0.98(4) . ? C3 C4 1.379(5) . ? C3 H3 0.94(3) . ? C4 C5 1.376(4) . ? C4 H4 0.95(3) . ? C5 C6 1.499(5) . ? C6 H6A 0.99(3) . ? C6 H6B 0.97(3) . ? C7 C8 1.477(4) . ? C8 C9 1.387(4) . ? C8 C10 1.391(4) . ? C9 C10 1.369(5) 3_665 ? C9 H9 0.92(3) . ? C10 C9 1.369(5) 3_665 ? C10 H10 0.97(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 C7 O1 C6 116.8(2) . . ? C1 N1 C5 115.9(4) . . ? N1 C1 C2 124.5(5) . . ? N1 C1 H1 116(2) . . ? C2 C1 H1 119(2) . . ? C3 C2 C1 118.4(4) . . ? C3 C2 H2 125(2) . . ? C1 C2 H2 117(2) . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 119.6(19) . . ? C4 C3 H3 120.8(19) . . ? C5 C4 C3 118.5(4) . . ? C5 C4 H4 117.4(19) . . ? C3 C4 H4 123.7(19) . . ? N1 C5 C4 123.3(3) . . ? N1 C5 C6 113.3(3) . . ? C4 C5 C6 123.4(3) . . ? O1 C6 C5 108.6(3) . . ? O1 C6 H6A 105.7(18) . . ? C5 C6 H6A 108.4(18) . . ? O1 C6 H6B 107.1(17) . . ? C5 C6 H6B 108.4(18) . . ? H6A C6 H6B 118(3) . . ? O2 C7 O1 123.1(3) . . ? O2 C7 C8 125.3(3) . . ? O1 C7 C8 111.6(2) . . ? C9 C8 C10 118.7(3) . . ? C9 C8 C7 122.9(3) . . ? C10 C8 C7 118.4(3) . . ? C10 C9 C8 120.8(3) 3_665 . ? C10 C9 H9 123.8(19) 3_665 . ? C8 C9 H9 115.2(19) . . ? C9 C10 C8 120.5(3) 3_665 . ? C9 C10 H10 120.3(17) 3_665 . ? C8 C10 H10 119.1(17) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.148 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.036 #===END data_complex1_77cffm _database_code_depnum_ccdc_archive 'CCDC 868388' #TrackingRef 'RSCadv-Frev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H35 Ag2 F6 N5 O14 S2' _chemical_formula_weight 1251.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2497(7) _cell_length_b 14.6138(8) _cell_length_c 15.2418(9) _cell_angle_alpha 85.752(2) _cell_angle_beta 73.7830(10) _cell_angle_gamma 72.581(3) _cell_volume 2295.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 7143 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 28.27 _exptl_crystal_description plates _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1252 _exptl_absorpt_coefficient_mu 1.043 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7588 _exptl_absorpt_correction_T_max 0.9212 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19515 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.99 _reflns_number_total 10313 _reflns_number_gt 9634 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material ? _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^)+(0.0568P)^2^+4.8102P] 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 10313 _refine_ls_number_parameters 654 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.01213(2) 0.333674(17) 0.075466(14) 0.02665(7) Uani 1 d . . . Ag2 Ag 0.00810(2) 0.115844(16) 0.021180(13) 0.02664(7) Uani 1 d . . . S1 S 0.69556(7) 0.31783(5) 0.20007(5) 0.02603(15) Uani 1 d . . . S2 S 0.32640(7) 0.17368(5) -0.09313(5) 0.02323(14) Uani 1 d . . . F1 F 0.5249(3) 0.3194(4) 0.1158(2) 0.1098(16) Uani 1 d . . . F2 F 0.44908(19) 0.41083(17) 0.23116(18) 0.0524(6) Uani 1 d . . . F3 F 0.5683(3) 0.4536(4) 0.1135(4) 0.154(3) Uani 1 d . . . F4 F 0.49984(19) 0.25420(17) -0.18831(13) 0.0421(5) Uani 1 d . . . F5 F 0.4488(2) 0.27871(18) -0.04264(14) 0.0469(6) Uani 1 d . . . F6 F 0.3170(2) 0.35446(15) -0.12017(16) 0.0456(5) Uani 1 d . . . O1 O -0.16269(17) 0.37856(14) 0.45878(12) 0.0192(4) Uani 1 d . . . O2 O -0.20434(19) 0.42081(18) 0.60550(13) 0.0298(5) Uani 1 d . . . O3 O -0.7973(2) 0.35718(18) 0.53877(14) 0.0294(5) Uani 1 d . . . O4 O -0.83470(17) 0.40580(14) 0.68274(12) 0.0189(4) Uani 1 d . . . O5 O 0.16790(17) 0.14079(14) -0.36753(12) 0.0184(4) Uani 1 d . . . O6 O 0.20363(19) 0.11051(16) -0.51667(13) 0.0254(4) Uani 1 d . . . O7 O 0.80279(18) 0.15245(16) -0.44158(13) 0.0247(4) Uani 1 d . . . O8 O 0.84253(17) 0.10956(14) -0.58789(12) 0.0186(4) Uani 1 d . . . O9 O 0.7919(2) 0.27834(19) 0.11809(15) 0.0356(5) Uani 1 d . . . O10 O 0.7209(3) 0.3935(3) 0.2385(3) 0.0920(16) Uani 1 d . . . O11 O 0.6533(4) 0.2515(3) 0.2621(3) 0.0949(16) Uani 1 d . . . O12 O 0.2824(2) 0.1759(2) -0.17343(15) 0.0376(5) Uani 1 d . . . O13 O 0.4287(3) 0.09037(19) -0.0843(2) 0.0468(6) Uani 1 d . . . O14 O 0.2232(2) 0.20476(16) -0.01064(14) 0.0294(5) Uani 1 d . . . N1 N 0.0788(2) 0.31028(17) 0.19802(15) 0.0202(4) Uani 1 d . . . N2 N -1.0504(2) 0.40180(17) 0.95818(16) 0.0213(5) Uani 1 d . . . N3 N -0.0617(2) 0.16840(17) -0.09874(15) 0.0207(4) Uani 1 d . . . N4 N 1.0782(2) 0.07802(17) -0.85676(16) 0.0209(4) Uani 1 d . . . N5 N 0.1879(3) -0.0346(2) -0.0793(2) 0.0331(6) Uani 1 d . . . C1 C 0.2056(3) 0.2686(2) 0.18887(18) 0.0221(5) Uani 1 d . . . H1 H 0.2583 0.2427 0.1324 0.027 Uiso 1 calc R . . C2 C 0.2603(3) 0.2629(2) 0.26016(19) 0.0243(6) Uani 1 d . . . H2 H 0.3486 0.2343 0.2514 0.029 Uiso 1 calc R . . C3 C 0.1829(3) 0.3001(2) 0.34487(18) 0.0213(5) Uani 1 d . . . H3 H 0.2182 0.2968 0.3938 0.026 Uiso 1 calc R . . C4 C 0.0511(2) 0.34271(18) 0.35556(17) 0.0178(5) Uani 1 d . . . C5 C 0.0028(3) 0.34679(19) 0.28040(18) 0.0192(5) Uani 1 d . . . H5 H -0.0850 0.3757 0.2871 0.023 Uiso 1 calc R . . C6 C -0.0326(2) 0.3835(2) 0.44747(18) 0.0204(5) Uani 1 d . . . H6A H 0.0023 0.3474 0.4952 0.024 Uiso 1 calc R . . H6B H -0.0339 0.4497 0.4521 0.024 Uiso 1 calc R . . C7 C -0.2407(2) 0.40010(19) 0.54433(17) 0.0187(5) Uani 1 d . . . C8 C -0.3738(2) 0.39402(18) 0.55476(17) 0.0169(5) Uani 1 d . . . C9 C -0.4598(3) 0.4124(2) 0.64173(18) 0.0206(5) Uani 1 d . . . H9 H -0.4323 0.4264 0.6900 0.025 Uiso 1 calc R . . C10 C -0.5856(3) 0.40982(19) 0.65633(18) 0.0199(5) Uani 1 d . . . H10 H -0.6431 0.4221 0.7143 0.024 Uiso 1 calc R . . C11 C -0.6259(2) 0.38868(18) 0.58372(17) 0.0167(5) Uani 1 d . . . C12 C -0.5399(2) 0.37010(18) 0.49637(17) 0.0180(5) Uani 1 d . . . H12 H -0.5673 0.3559 0.4482 0.022 Uiso 1 calc R . . C13 C -0.4134(2) 0.37302(18) 0.48184(17) 0.0175(5) Uani 1 d . . . H13 H -0.3558 0.3610 0.4239 0.021 Uiso 1 calc R . . C14 C -0.7596(2) 0.38202(18) 0.59727(17) 0.0175(5) Uani 1 d . . . C15 C -0.9608(2) 0.3894(2) 0.70094(18) 0.0208(5) Uani 1 d . . . H15A H -0.9502 0.3221 0.6919 0.025 Uiso 1 calc R . . H15B H -1.0079 0.4267 0.6594 0.025 Uiso 1 calc R . . C16 C -1.0342(2) 0.41892(19) 0.79777(18) 0.0176(5) Uani 1 d . . . C17 C -1.1572(3) 0.4847(2) 0.8171(2) 0.0238(5) Uani 1 d . . . H17 H -1.1939 0.5120 0.7702 0.029 Uiso 1 calc R . . C18 C -1.2240(3) 0.5087(2) 0.9075(2) 0.0282(6) Uani 1 d . . . H18 H -1.3060 0.5527 0.9221 0.034 Uiso 1 calc R . . C19 C -1.1677(3) 0.4667(2) 0.9755(2) 0.0250(6) Uani 1 d . . . H19 H -1.2127 0.4839 1.0359 0.030 Uiso 1 calc R . . C20 C -0.9856(3) 0.3787(2) 0.87051(18) 0.0200(5) Uani 1 d . . . H20 H -0.9043 0.3337 0.8581 0.024 Uiso 1 calc R . . C21 C -0.1832(3) 0.2274(2) -0.08520(19) 0.0235(5) Uani 1 d . . . H21 H -0.2317 0.2463 -0.0258 0.028 Uiso 1 calc R . . C22 C -0.2384(3) 0.2608(2) -0.1560(2) 0.0252(6) Uani 1 d . . . H22 H -0.3220 0.3023 -0.1443 0.030 Uiso 1 calc R . . C23 C -0.1679(3) 0.2317(2) -0.24473(19) 0.0214(5) Uani 1 d . . . H23 H -0.2041 0.2522 -0.2932 0.026 Uiso 1 calc R . . C24 C -0.0418(2) 0.17125(18) -0.26007(17) 0.0170(5) Uani 1 d . . . C25 C 0.0072(3) 0.1416(2) -0.18528(18) 0.0196(5) Uani 1 d . . . H25 H 0.0914 0.1013 -0.1953 0.023 Uiso 1 calc R . . C26 C 0.0358(2) 0.1390(2) -0.35574(18) 0.0193(5) Uani 1 d . . . H26A H 0.0351 0.0745 -0.3663 0.023 Uiso 1 calc R . . H26B H -0.0015 0.1813 -0.3994 0.023 Uiso 1 calc R . . C27 C 0.2424(2) 0.12517(18) -0.45429(17) 0.0176(5) Uani 1 d . . . C28 C 0.3772(2) 0.12747(18) -0.46460(17) 0.0166(5) Uani 1 d . . . C29 C 0.4610(3) 0.11634(19) -0.55249(17) 0.0192(5) Uani 1 d . . . H29 H 0.4317 0.1085 -0.6020 0.023 Uiso 1 calc R . . C30 C 0.5882(2) 0.11695(19) -0.56625(17) 0.0189(5) Uani 1 d . . . H30 H 0.6442 0.1096 -0.6248 0.023 Uiso 1 calc R . . C31 C 0.6309(2) 0.12868(18) -0.49151(17) 0.0164(5) Uani 1 d . . . C32 C 0.5471(2) 0.14041(19) -0.40361(18) 0.0189(5) Uani 1 d . . . H32 H 0.5762 0.1487 -0.3542 0.023 Uiso 1 calc R . . C33 C 0.4198(2) 0.13965(19) -0.38996(17) 0.0184(5) Uani 1 d . . . H33 H 0.3636 0.1472 -0.3315 0.022 Uiso 1 calc R . . C34 C 0.7657(2) 0.13214(18) -0.50271(17) 0.0170(5) Uani 1 d . . . C35 C 0.9728(2) 0.1147(2) -0.60023(17) 0.0189(5) Uani 1 d . . . H35A H 1.0110 0.0744 -0.5559 0.023 Uiso 1 calc R . . H35B H 0.9706 0.1802 -0.5907 0.023 Uiso 1 calc R . . C36 C 1.0531(2) 0.08168(18) -0.69542(17) 0.0171(5) Uani 1 d . . . C37 C 1.1834(3) 0.0315(2) -0.70897(19) 0.0211(5) Uani 1 d . . . H37 H 1.2188 0.0159 -0.6596 0.025 Uiso 1 calc R . . C38 C 1.2598(3) 0.0049(2) -0.7971(2) 0.0239(5) Uani 1 d . . . H38 H 1.3468 -0.0293 -0.8077 0.029 Uiso 1 calc R . . C39 C 1.2042(3) 0.0301(2) -0.86866(19) 0.0234(5) Uani 1 d . . . H39 H 1.2560 0.0133 -0.9278 0.028 Uiso 1 calc R . . C40 C 1.0044(3) 0.10304(19) -0.77111(18) 0.0188(5) Uani 1 d . . . H40 H 0.9172 0.1360 -0.7623 0.023 Uiso 1 calc R . . C41 C 0.5528(3) 0.3809(3) 0.1629(3) 0.0420(8) Uani 1 d . . . C42 C 0.4022(3) 0.2699(2) -0.1117(2) 0.0307(6) Uani 1 d . . . C43 C 0.4156(6) -0.0777(5) -0.1890(4) 0.0819(16) Uiso 1 d . . . H43A H 0.4221 -0.1275 -0.2293 0.123 Uiso 1 calc R . . H43B H 0.4848 -0.0981 -0.1601 0.123 Uiso 1 calc R . . H43C H 0.4214 -0.0207 -0.2234 0.123 Uiso 1 calc R . . C44 C 0.2889(4) -0.0572(3) -0.1178(4) 0.0599(13) Uani 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 0.02501(12) 0.03925(14) 0.01544(11) -0.00055(9) -0.00661(8) -0.00770(9) Ag2 0.02676(13) 0.03830(14) 0.01423(11) 0.00071(9) -0.00650(8) -0.00774(10) S1 0.0248(3) 0.0311(4) 0.0177(3) -0.0034(3) -0.0057(3) -0.0007(3) S2 0.0210(3) 0.0259(3) 0.0193(3) -0.0045(2) 0.0009(2) -0.0064(3) F1 0.0376(14) 0.224(5) 0.0715(19) -0.081(3) -0.0175(13) -0.022(2) F2 0.0222(10) 0.0552(13) 0.0761(17) -0.0208(12) -0.0075(10) -0.0061(9) F3 0.0391(16) 0.173(4) 0.219(5) 0.166(4) -0.034(2) -0.024(2) F4 0.0331(10) 0.0688(14) 0.0276(10) 0.0008(9) 0.0017(8) -0.0287(10) F5 0.0489(12) 0.0763(16) 0.0311(10) -0.0064(10) -0.0123(9) -0.0379(12) F6 0.0558(13) 0.0306(10) 0.0483(13) 0.0036(9) -0.0086(10) -0.0155(9) O1 0.0136(8) 0.0296(10) 0.0145(8) -0.0023(7) -0.0019(7) -0.0076(7) O2 0.0192(10) 0.0554(14) 0.0165(9) -0.0075(9) -0.0021(7) -0.0139(9) O3 0.0200(10) 0.0523(14) 0.0176(9) -0.0070(9) -0.0037(8) -0.0125(9) O4 0.0143(8) 0.0272(9) 0.0155(8) -0.0017(7) -0.0002(7) -0.0094(7) O5 0.0132(8) 0.0289(10) 0.0136(8) -0.0018(7) -0.0017(6) -0.0082(7) O6 0.0191(9) 0.0447(12) 0.0149(9) -0.0043(8) -0.0034(7) -0.0129(9) O7 0.0174(9) 0.0411(12) 0.0163(9) -0.0047(8) -0.0028(7) -0.0102(8) O8 0.0131(8) 0.0273(9) 0.0152(8) -0.0019(7) -0.0018(7) -0.0073(7) O9 0.0263(11) 0.0542(15) 0.0230(11) -0.0123(10) -0.0013(9) -0.0091(10) O10 0.0326(15) 0.099(3) 0.146(4) -0.089(3) -0.0365(19) 0.0125(16) O11 0.068(2) 0.089(3) 0.076(2) 0.056(2) 0.0207(19) 0.002(2) O12 0.0351(12) 0.0594(16) 0.0234(11) -0.0099(10) -0.0039(9) -0.0226(11) O13 0.0376(14) 0.0350(13) 0.0554(17) -0.0030(12) -0.0043(12) 0.0008(11) O14 0.0268(11) 0.0362(12) 0.0201(10) -0.0051(9) 0.0036(8) -0.0097(9) N1 0.0215(11) 0.0243(11) 0.0148(10) -0.0008(8) -0.0036(8) -0.0076(9) N2 0.0187(11) 0.0278(12) 0.0170(11) 0.0002(9) -0.0034(8) -0.0077(9) N3 0.0207(11) 0.0281(12) 0.0137(10) -0.0008(9) -0.0027(8) -0.0094(9) N4 0.0194(11) 0.0273(11) 0.0152(10) 0.0009(9) -0.0030(8) -0.0073(9) N5 0.0316(14) 0.0330(14) 0.0334(14) -0.0009(11) -0.0047(11) -0.0110(11) C1 0.0218(13) 0.0236(13) 0.0171(12) -0.0029(10) 0.0004(10) -0.0054(10) C2 0.0182(13) 0.0283(14) 0.0213(13) -0.0005(11) -0.0016(10) -0.0023(11) C3 0.0188(12) 0.0262(13) 0.0181(12) 0.0000(10) -0.0052(10) -0.0050(10) C4 0.0180(12) 0.0203(12) 0.0144(11) -0.0003(9) -0.0011(9) -0.0076(10) C5 0.0165(12) 0.0239(12) 0.0171(12) -0.0003(10) -0.0032(9) -0.0070(10) C6 0.0145(11) 0.0312(14) 0.0162(12) -0.0029(10) -0.0026(9) -0.0083(10) C7 0.0164(12) 0.0230(12) 0.0157(11) 0.0006(9) -0.0025(9) -0.0059(10) C8 0.0145(11) 0.0186(11) 0.0163(11) 0.0000(9) -0.0029(9) -0.0039(9) C9 0.0196(12) 0.0274(13) 0.0154(12) -0.0034(10) -0.0024(10) -0.0091(10) C10 0.0189(12) 0.0240(12) 0.0153(11) -0.0014(10) -0.0013(9) -0.0068(10) C11 0.0145(11) 0.0164(11) 0.0176(12) 0.0016(9) -0.0031(9) -0.0038(9) C12 0.0182(12) 0.0209(12) 0.0154(11) 0.0002(9) -0.0061(9) -0.0048(9) C13 0.0154(11) 0.0209(12) 0.0137(11) -0.0005(9) -0.0010(9) -0.0041(9) C14 0.0158(11) 0.0190(11) 0.0158(11) 0.0003(9) -0.0023(9) -0.0045(9) C15 0.0155(12) 0.0308(14) 0.0183(12) -0.0002(10) -0.0023(9) -0.0120(10) C16 0.0160(11) 0.0211(12) 0.0176(12) 0.0023(9) -0.0033(9) -0.0097(9) C17 0.0202(13) 0.0249(13) 0.0238(13) 0.0053(11) -0.0045(10) -0.0055(10) C18 0.0192(13) 0.0274(14) 0.0289(15) 0.0010(12) -0.0003(11) 0.0004(11) C19 0.0230(13) 0.0269(14) 0.0205(13) -0.0020(11) 0.0019(10) -0.0073(11) C20 0.0148(12) 0.0273(13) 0.0178(12) 0.0003(10) -0.0035(9) -0.0070(10) C21 0.0195(13) 0.0318(14) 0.0177(12) -0.0050(11) 0.0005(10) -0.0090(11) C22 0.0155(12) 0.0321(15) 0.0254(14) -0.0052(11) -0.0031(10) -0.0038(11) C23 0.0163(12) 0.0281(13) 0.0210(13) 0.0009(10) -0.0061(10) -0.0073(10) C24 0.0161(11) 0.0210(12) 0.0147(11) -0.0017(9) -0.0010(9) -0.0091(9) C25 0.0161(12) 0.0254(13) 0.0168(12) 0.0001(10) -0.0030(9) -0.0067(10) C26 0.0140(11) 0.0298(13) 0.0157(12) -0.0017(10) -0.0025(9) -0.0096(10) C27 0.0156(11) 0.0211(12) 0.0147(11) -0.0003(9) -0.0020(9) -0.0053(9) C28 0.0150(11) 0.0187(11) 0.0148(11) -0.0004(9) -0.0017(9) -0.0051(9) C29 0.0186(12) 0.0261(13) 0.0135(11) -0.0004(10) -0.0043(9) -0.0071(10) C30 0.0163(12) 0.0246(12) 0.0136(11) -0.0008(9) -0.0011(9) -0.0054(10) C31 0.0141(11) 0.0174(11) 0.0167(12) 0.0001(9) -0.0030(9) -0.0040(9) C32 0.0173(12) 0.0249(12) 0.0149(12) -0.0007(10) -0.0049(9) -0.0058(10) C33 0.0149(11) 0.0238(12) 0.0141(11) -0.0018(9) -0.0012(9) -0.0041(9) C34 0.0166(12) 0.0190(11) 0.0145(11) 0.0004(9) -0.0026(9) -0.0054(9) C35 0.0140(11) 0.0282(13) 0.0159(12) -0.0014(10) -0.0030(9) -0.0086(10) C36 0.0158(11) 0.0196(11) 0.0164(12) 0.0008(9) -0.0018(9) -0.0084(9) C37 0.0187(12) 0.0251(13) 0.0199(12) 0.0023(10) -0.0066(10) -0.0061(10) C38 0.0166(12) 0.0268(13) 0.0250(14) -0.0014(11) -0.0022(10) -0.0041(10) C39 0.0208(13) 0.0268(13) 0.0183(12) -0.0034(10) 0.0010(10) -0.0058(11) C40 0.0155(11) 0.0227(12) 0.0170(12) 0.0004(10) -0.0024(9) -0.0056(10) C41 0.0235(16) 0.057(2) 0.046(2) 0.0108(17) -0.0123(14) -0.0136(15) C42 0.0299(15) 0.0421(17) 0.0235(14) 0.0001(12) -0.0052(12) -0.0174(13) C44 0.042(2) 0.0323(19) 0.094(4) -0.030(2) 0.014(2) -0.0172(16) _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 2.168(2) 1_654 ? Ag1 N1 2.169(2) . ? Ag1 Ag2 3.3642(4) . ? Ag2 N3 2.186(2) . ? Ag2 N4 2.190(2) 1_456 ? Ag2 N5 2.716(3) . ? S1 O11 1.397(3) . ? S1 O10 1.423(3) . ? S1 O9 1.430(2) . ? S1 C41 1.815(4) . ? S2 O13 1.431(3) . ? S2 O12 1.438(2) . ? S2 O14 1.445(2) . ? S2 C42 1.818(3) . ? F1 C41 1.346(5) . ? F2 C41 1.312(4) . ? F3 C41 1.282(5) . ? F4 C42 1.339(3) . ? F5 C42 1.330(4) . ? F6 C42 1.341(4) . ? O1 C7 1.351(3) . ? O1 C6 1.449(3) . ? O2 C7 1.207(3) . ? O3 C14 1.208(3) . ? O4 C14 1.345(3) . ? O4 C15 1.456(3) . ? O5 C27 1.347(3) . ? O5 C26 1.454(3) . ? O6 C27 1.207(3) . ? O7 C34 1.209(3) . ? O8 C34 1.345(3) . ? O8 C35 1.449(3) . ? N1 C1 1.345(4) . ? N1 C5 1.349(3) . ? N2 C19 1.343(4) . ? N2 C20 1.344(3) . ? N2 Ag1 2.168(2) 1_456 ? N3 C25 1.348(3) . ? N3 C21 1.348(4) . ? N4 C40 1.346(3) . ? N4 C39 1.347(4) . ? N4 Ag2 2.190(2) 1_654 ? N5 C44 1.084(5) . ? C1 C2 1.376(4) . ? C1 H1 0.9300 . ? C2 C3 1.383(4) . ? C2 H2 0.9300 . ? C3 C4 1.392(4) . ? C3 H3 0.9300 . ? C4 C5 1.389(4) . ? C4 C6 1.502(3) . ? C5 H5 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.490(3) . ? C8 C13 1.392(4) . ? C8 C9 1.395(3) . ? C9 C10 1.382(4) . ? C9 H9 0.9300 . ? C10 C11 1.393(4) . ? C10 H10 0.9300 . ? C11 C12 1.400(3) . ? C11 C14 1.491(3) . ? C12 C13 1.391(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C15 C16 1.499(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C20 1.387(4) . ? C16 C17 1.395(4) . ? C17 C18 1.387(4) . ? C17 H17 0.9300 . ? C18 C19 1.375(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.379(4) . ? C21 H21 0.9300 . ? C22 C23 1.387(4) . ? C22 H22 0.9300 . ? C23 C24 1.393(4) . ? C23 H23 0.9300 . ? C24 C25 1.388(4) . ? C24 C26 1.502(3) . ? C25 H25 0.9300 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.491(3) . ? C28 C33 1.393(4) . ? C28 C29 1.394(3) . ? C29 C30 1.389(4) . ? C29 H29 0.9300 . ? C30 C31 1.394(4) . ? C30 H30 0.9300 . ? C31 C32 1.395(3) . ? C31 C34 1.493(3) . ? C32 C33 1.391(4) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C35 C36 1.505(3) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C40 1.388(4) . ? C36 C37 1.393(4) . ? C37 C38 1.388(4) . ? C37 H37 0.9300 . ? C38 C39 1.379(4) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C43 C44 1.493(7) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 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 N2 Ag1 N1 161.93(9) 1_654 . ? N2 Ag1 Ag2 93.58(6) 1_654 . ? N1 Ag1 Ag2 104.43(6) . . ? N3 Ag2 N4 174.21(9) . 1_456 ? N3 Ag2 N5 89.83(9) . . ? N4 Ag2 N5 94.04(9) 1_456 . ? N3 Ag2 Ag1 93.35(6) . . ? N4 Ag2 Ag1 80.86(6) 1_456 . ? N5 Ag2 Ag1 133.80(6) . . ? O11 S1 O10 115.7(3) . . ? O11 S1 O9 115.8(2) . . ? O10 S1 O9 113.2(2) . . ? O11 S1 C41 103.1(2) . . ? O10 S1 C41 102.1(2) . . ? O9 S1 C41 104.70(16) . . ? O13 S2 O12 115.43(17) . . ? O13 S2 O14 115.42(15) . . ? O12 S2 O14 113.96(14) . . ? O13 S2 C42 103.67(16) . . ? O12 S2 C42 103.49(15) . . ? O14 S2 C42 102.48(14) . . ? C7 O1 C6 113.78(19) . . ? C14 O4 C15 113.9(2) . . ? C27 O5 C26 113.84(19) . . ? C34 O8 C35 113.65(19) . . ? C1 N1 C5 118.5(2) . . ? C1 N1 Ag1 118.01(18) . . ? C5 N1 Ag1 122.89(18) . . ? C19 N2 C20 118.0(2) . . ? C19 N2 Ag1 116.72(18) . 1_456 ? C20 N2 Ag1 125.03(19) . 1_456 ? C25 N3 C21 117.9(2) . . ? C25 N3 Ag2 123.89(19) . . ? C21 N3 Ag2 118.12(18) . . ? C40 N4 C39 118.1(2) . . ? C40 N4 Ag2 124.02(18) . 1_654 ? C39 N4 Ag2 117.79(18) . 1_654 ? C44 N5 Ag2 141.1(3) . . ? N1 C1 C2 122.3(2) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 C6 122.7(2) . . ? C3 C4 C6 118.7(2) . . ? N1 C5 C4 122.3(2) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? O1 C6 C4 109.3(2) . . ? O1 C6 H6A 109.8 . . ? C4 C6 H6A 109.8 . . ? O1 C6 H6B 109.8 . . ? C4 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? O2 C7 O1 122.8(2) . . ? O2 C7 C8 124.2(2) . . ? O1 C7 C8 113.0(2) . . ? C13 C8 C9 120.6(2) . . ? C13 C8 C7 122.6(2) . . ? C9 C8 C7 116.8(2) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.6(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.5(2) . . ? C10 C11 C14 121.2(2) . . ? C12 C11 C14 118.3(2) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C8 119.4(2) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? O3 C14 O4 122.9(2) . . ? O3 C14 C11 124.3(2) . . ? O4 C14 C11 112.7(2) . . ? O4 C15 C16 108.3(2) . . ? O4 C15 H15A 110.0 . . ? C16 C15 H15A 110.0 . . ? O4 C15 H15B 110.0 . . ? C16 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? C20 C16 C17 118.1(2) . . ? C20 C16 C15 121.6(2) . . ? C17 C16 C15 120.2(2) . . ? C18 C17 C16 118.8(3) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C19 C18 C17 119.2(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? N2 C19 C18 122.7(3) . . ? N2 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? N2 C20 C16 123.0(2) . . ? N2 C20 H20 118.5 . . ? C16 C20 H20 118.5 . . ? N3 C21 C22 122.6(3) . . ? N3 C21 H21 118.7 . . ? C22 C21 H21 118.7 . . ? C21 C22 C23 119.2(3) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C22 C23 C24 118.9(3) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? C25 C24 C23 118.3(2) . . ? C25 C24 C26 122.1(2) . . ? C23 C24 C26 119.6(2) . . ? N3 C25 C24 123.0(2) . . ? N3 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? O5 C26 C24 108.7(2) . . ? O5 C26 H26A 110.0 . . ? C24 C26 H26A 110.0 . . ? O5 C26 H26B 110.0 . . ? C24 C26 H26B 110.0 . . ? H26A C26 H26B 108.3 . . ? O6 C27 O5 123.3(2) . . ? O6 C27 C28 123.9(2) . . ? O5 C27 C28 112.8(2) . . ? C33 C28 C29 120.5(2) . . ? C33 C28 C27 122.0(2) . . ? C29 C28 C27 117.5(2) . . ? C30 C29 C28 120.1(2) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C31 119.4(2) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? C30 C31 C32 120.6(2) . . ? C30 C31 C34 121.6(2) . . ? C32 C31 C34 117.8(2) . . ? C33 C32 C31 119.9(2) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C28 119.5(2) . . ? C32 C33 H33 120.3 . . ? C28 C33 H33 120.3 . . ? O7 C34 O8 123.1(2) . . ? O7 C34 C31 123.8(2) . . ? O8 C34 C31 113.1(2) . . ? O8 C35 C36 109.5(2) . . ? O8 C35 H35A 109.8 . . ? C36 C35 H35A 109.8 . . ? O8 C35 H35B 109.8 . . ? C36 C35 H35B 109.8 . . ? H35A C35 H35B 108.2 . . ? C40 C36 C37 118.4(2) . . ? C40 C36 C35 122.7(2) . . ? C37 C36 C35 118.8(2) . . ? C38 C37 C36 119.2(3) . . ? C38 C37 H37 120.4 . . ? C36 C37 H37 120.4 . . ? C39 C38 C37 118.7(3) . . ? C39 C38 H38 120.6 . . ? C37 C38 H38 120.6 . . ? N4 C39 C38 122.9(3) . . ? N4 C39 H39 118.6 . . ? C38 C39 H39 118.6 . . ? N4 C40 C36 122.6(2) . . ? N4 C40 H40 118.7 . . ? C36 C40 H40 118.7 . . ? F3 C41 F2 107.9(4) . . ? F3 C41 F1 110.1(5) . . ? F2 C41 F1 104.8(3) . . ? F3 C41 S1 112.2(3) . . ? F2 C41 S1 112.9(3) . . ? F1 C41 S1 108.8(3) . . ? F5 C42 F4 108.1(3) . . ? F5 C42 F6 107.2(3) . . ? F4 C42 F6 107.7(3) . . ? F5 C42 S2 111.8(2) . . ? F4 C42 S2 110.9(2) . . ? F6 C42 S2 111.0(2) . . ? C44 C43 H43A 109.5 . . ? C44 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C44 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? N5 C44 C43 166.6(6) . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.734 _refine_diff_density_min -1.098 _refine_diff_density_rms 0.104 #===END data_complex2_61cff _database_code_depnum_ccdc_archive 'CCDC 868389' #TrackingRef 'RSCadv-Frev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Ag F3 N2 O8 S' _chemical_formula_weight 623.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.9957(11) _cell_length_b 23.128(4) _cell_length_c 16.303(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2260.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2433 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 24.56 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 1.061 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6762 _exptl_absorpt_correction_T_max 0.9588 _exptl_absorpt_process_detail 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12013 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2475 _reflns_number_gt 2107 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material ? _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^)+(0.0465P)^2^+3.4743P] 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 2475 _refine_ls_number_parameters 178 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.0000 0.335186(17) 0.7500 0.04528(15) Uani 1 d S . . O1 O 0.5312(4) 0.41831(11) 0.92205(14) 0.0455(6) Uani 1 d . . . O2 O 0.7417(5) 0.44050(12) 0.81368(13) 0.0530(6) Uani 1 d . . . N1 N 0.0429(4) 0.33159(11) 0.88076(17) 0.0374(6) Uani 1 d . . . C1 C -0.1173(6) 0.30469(15) 0.9242(2) 0.0449(8) Uani 1 d . . . H1 H -0.2310 0.2859 0.8959 0.054 Uiso 1 calc R . . C2 C -0.1206(7) 0.30367(16) 1.0083(2) 0.0495(9) Uani 1 d . . . H2 H -0.2359 0.2855 1.0364 0.059 Uiso 1 calc R . . C3 C 0.0498(7) 0.33005(17) 1.0501(2) 0.0525(10) Uani 1 d . . . H3 H 0.0518 0.3300 1.1071 0.063 Uiso 1 calc R . . C4 C 0.2182(6) 0.35673(16) 1.00668(18) 0.0456(8) Uani 1 d . . . H4 H 0.3367 0.3740 1.0342 0.055 Uiso 1 calc R . . C5 C 0.2094(5) 0.35766(13) 0.92191(17) 0.0356(7) Uani 1 d . . . C6 C 0.3813(6) 0.38665(15) 0.86937(18) 0.0412(7) Uani 1 d . . . H6A H 0.4634 0.3580 0.8382 0.049 Uiso 1 calc R . . H6B H 0.3096 0.4128 0.8311 0.049 Uiso 1 calc R . . C7 C 0.7058(5) 0.44341(14) 0.88563(18) 0.0379(7) Uani 1 d . . . C8 C 0.8533(5) 0.47347(13) 0.94583(18) 0.0362(7) Uani 1 d . . . C9 C 0.8190(6) 0.46946(15) 1.03005(19) 0.0419(7) Uani 1 d . . . H9 H 0.6975 0.4489 1.0502 0.050 Uiso 1 calc R . . C10 C 1.0354(5) 0.50402(16) 0.9161(2) 0.0429(8) Uani 1 d . . . H10 H 1.0594 0.5066 0.8598 0.052 Uiso 1 calc R . . O8 O 0.5000 0.2689(3) 0.7500 0.114(2) Uani 1 d SD . . H8C H 0.373(8) 0.247(3) 0.759(4) 0.13(3) Uiso 1 d D . . O9 O -0.0018(15) 0.1907(3) 0.8241(4) 0.216(5) Uani 1 d . . . O10 O 0.2578(19) 0.1707(5) 0.7508(6) 0.152(5) Uani 0.50 d P . . S1 S 0.0000 0.17087(8) 0.7500 0.0738(5) Uani 1 d S . . C11 C 0.0000 0.0957(4) 0.7500 0.117(5) Uani 1 d S . . F1 F 0.2610(16) 0.0883(4) 0.7523(6) 0.153(4) Uani 0.50 d P . . F2 F -0.0061(10) 0.0688(2) 0.8141(3) 0.167(3) Uani 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 0.0478(2) 0.0602(3) 0.0279(2) 0.000 -0.01137(14) 0.000 O1 0.0469(14) 0.0571(15) 0.0325(11) -0.0086(10) -0.0057(10) -0.0105(11) O2 0.0588(16) 0.0691(16) 0.0312(12) -0.0072(11) -0.0012(11) -0.0134(13) N1 0.0401(15) 0.0410(14) 0.0310(13) -0.0001(11) -0.0076(11) 0.0008(11) C1 0.044(2) 0.0471(19) 0.0436(18) 0.0010(15) -0.0060(15) -0.0013(16) C2 0.053(2) 0.052(2) 0.0427(18) 0.0050(16) 0.0030(16) -0.0057(17) C3 0.067(3) 0.061(2) 0.0287(16) 0.0051(15) -0.0012(16) 0.0007(19) C4 0.053(2) 0.053(2) 0.0301(15) -0.0018(14) -0.0105(15) -0.0025(17) C5 0.0419(17) 0.0357(15) 0.0292(14) -0.0005(12) -0.0060(13) 0.0045(13) C6 0.0464(19) 0.0502(19) 0.0269(14) -0.0055(13) -0.0071(14) -0.0038(15) C7 0.0412(18) 0.0394(17) 0.0331(15) -0.0034(13) -0.0029(13) 0.0026(14) C8 0.0398(16) 0.0373(16) 0.0316(14) -0.0042(12) -0.0030(13) 0.0027(13) C9 0.0419(18) 0.0490(18) 0.0348(15) -0.0016(14) 0.0016(14) -0.0067(15) C10 0.045(2) 0.0530(19) 0.0312(15) -0.0039(14) -0.0002(13) -0.0042(15) O8 0.139(7) 0.059(3) 0.146(6) 0.000 -0.036(5) 0.000 O9 0.379(14) 0.128(4) 0.140(6) -0.081(4) 0.022(6) -0.022(5) O10 0.082(7) 0.201(12) 0.173(12) -0.022(8) 0.021(6) -0.073(7) S1 0.0902(13) 0.0650(10) 0.0660(11) 0.000 0.0267(9) 0.000 C11 0.230(15) 0.071(5) 0.052(4) 0.000 -0.019(6) 0.000 F1 0.120(8) 0.109(6) 0.230(13) -0.001(6) -0.028(7) 0.062(6) F2 0.273(8) 0.114(3) 0.115(3) 0.055(3) -0.050(3) -0.040(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.149(3) 3_556 ? Ag1 N1 2.149(3) . ? O1 C7 1.336(4) . ? O1 C6 1.443(4) . ? O2 C7 1.194(4) . ? N1 C5 1.345(4) . ? N1 C1 1.346(5) . ? C1 C2 1.372(5) . ? C1 H1 0.9300 . ? C2 C3 1.371(5) . ? C2 H2 0.9300 . ? C3 C4 1.378(5) . ? C3 H3 0.9300 . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.499(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.493(4) . ? C8 C10 1.388(5) . ? C8 C9 1.392(4) . ? C9 C10 1.382(4) 5_767 ? C9 H9 0.9300 . ? C10 C9 1.382(4) 5_767 ? C10 H10 0.9300 . ? O8 H8C 0.93(2) . ? O9 S1 1.292(6) . ? O10 S1 1.546(12) . ? S1 O9 1.292(6) 3_556 ? S1 O10 1.546(12) 3_556 ? S1 C11 1.737(9) . ? C11 F2 1.216(6) 3_556 ? C11 F2 1.216(6) . ? C11 F1 1.575(9) 3_556 ? C11 F1 1.575(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 N1 175.57(14) 3_556 . ? C7 O1 C6 116.4(2) . . ? C5 N1 C1 118.3(3) . . ? C5 N1 Ag1 124.5(2) . . ? C1 N1 Ag1 117.0(2) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 118.5(4) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.3(3) . . ? N1 C5 C6 115.2(3) . . ? C4 C5 C6 123.5(3) . . ? O1 C6 C5 108.4(2) . . ? O1 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? O1 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? O2 C7 O1 123.6(3) . . ? O2 C7 C8 124.4(3) . . ? O1 C7 C8 112.0(3) . . ? C10 C8 C9 119.7(3) . . ? C10 C8 C7 118.2(3) . . ? C9 C8 C7 122.0(3) . . ? C10 C9 C8 120.3(3) 5_767 . ? C10 C9 H9 119.9 5_767 . ? C8 C9 H9 119.9 . . ? C9 C10 C8 120.0(3) 5_767 . ? C9 C10 H10 120.0 5_767 . ? C8 C10 H10 120.0 . . ? O9 S1 O9 138.5(7) . 3_556 ? O9 S1 O10 90.1(5) . . ? O9 S1 O10 90.0(5) 3_556 . ? O9 S1 O10 90.0(5) . 3_556 ? O9 S1 O10 90.1(5) 3_556 3_556 ? O10 S1 O10 179.7(10) . 3_556 ? O9 S1 C11 110.7(4) . . ? O9 S1 C11 110.7(4) 3_556 . ? O10 S1 C11 89.8(5) . . ? O10 S1 C11 89.8(5) 3_556 . ? F2 C11 F2 118.5(9) 3_556 . ? F2 C11 F1 87.3(5) 3_556 3_556 ? F2 C11 F1 86.2(5) . 3_556 ? F2 C11 F1 86.2(5) 3_556 . ? F2 C11 F1 87.3(5) . . ? F1 C11 F1 167.4(10) 3_556 . ? F2 C11 S1 120.8(4) 3_556 . ? F2 C11 S1 120.8(4) . . ? F1 C11 S1 96.3(5) 3_556 . ? F1 C11 S1 96.3(5) . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.574 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.072