# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Huang, Wei' _publ_contact_author_email whuang@nju.edu.cn _publ_section_title ; Linear extension of bithiophene compounds by the combination of C-N covalent bond cross-coupling and N-Ag coordinative bond formation ; _publ_author_name 'Wei Huang' # Attachment '- Four Cifs.cif' data_L _database_code_depnum_ccdc_archive 'CCDC 792210' #TrackingRef '- Four Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 N4 S2' _chemical_formula_sum 'C14 H10 N4 S2' _chemical_formula_weight 298.40 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.9135(14) _cell_length_b 7.475(3) _cell_length_c 22.656(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.447(7) _cell_angle_gamma 90.00 _cell_volume 659.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2484 _cell_measurement_theta_min 2.871 _cell_measurement_theta_max 28.181 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9248 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3090 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1150 _reflns_number_gt 1061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+4.3669P] 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 1150 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.1913 _refine_ls_wR_factor_gt 0.1895 _refine_ls_goodness_of_fit_ref 1.212 _refine_ls_restrained_S_all 1.212 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0977(16) 0.2519(9) 0.3893(2) 0.0375(14) Uani 1 1 d . . . C2 C -0.0661(17) 0.4027(9) 0.3698(3) 0.0409(15) Uani 1 1 d . . . H2 H -0.1377 0.4256 0.3302 0.049 Uiso 1 1 calc R . . C3 C -0.1156(17) 0.5215(9) 0.4167(3) 0.0403(15) Uani 1 1 d . . . H3 H -0.2230 0.6319 0.4110 0.048 Uiso 1 1 calc R . . C4 C 0.0078(15) 0.4600(8) 0.4710(2) 0.0314(13) Uani 1 1 d . . . C5 C 0.282(2) 0.1178(10) 0.2983(3) 0.0493(17) Uani 1 1 d . . . H5 H 0.2821 0.2237 0.2767 0.059 Uiso 1 1 calc R . . C6 C 0.330(2) -0.1543(10) 0.3221(3) 0.0529(18) Uani 1 1 d . . . H6 H 0.3711 -0.2766 0.3200 0.064 Uiso 1 1 calc R . . C7 C 0.2326(19) -0.0688(8) 0.3705(3) 0.0452(17) Uani 1 1 d . . . H7 H 0.1941 -0.1197 0.4067 0.054 Uiso 1 1 calc R . . N1 N 0.2023(13) 0.1087(7) 0.3550(2) 0.0357(12) Uani 1 1 d . . . N2 N 0.3595(17) -0.0370(8) 0.2771(2) 0.0513(15) Uani 1 1 d . . . S1 S 0.1954(4) 0.2505(2) 0.46555(6) 0.0380(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.045(3) 0.039(3) 0.027(3) -0.005(3) 0.000(3) -0.005(3) C2 0.056(4) 0.037(3) 0.028(3) 0.003(3) -0.004(3) 0.002(3) C3 0.052(4) 0.036(3) 0.032(3) 0.003(3) -0.006(3) 0.003(3) C4 0.038(3) 0.028(3) 0.028(3) -0.001(2) -0.001(2) -0.002(2) C5 0.076(5) 0.045(4) 0.026(3) 0.001(3) 0.006(3) -0.002(4) C6 0.068(5) 0.042(4) 0.046(4) -0.003(3) -0.007(3) 0.007(4) C7 0.072(5) 0.034(3) 0.029(3) 0.002(3) 0.007(3) 0.001(3) N1 0.049(3) 0.032(3) 0.026(2) -0.004(2) 0.001(2) -0.003(2) N2 0.071(4) 0.050(4) 0.031(3) -0.010(3) -0.001(3) 0.006(3) S1 0.0484(9) 0.0371(8) 0.0275(7) 0.0010(6) -0.0025(6) 0.0047(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 C1 C2 1.350(9) . ? C1 N1 1.406(8) . ? C1 S1 1.733(6) . ? C2 C3 1.413(9) . ? C2 H2 0.9300 . ? C3 C4 1.357(8) . ? C3 H3 0.9300 . ? C4 C4 1.450(11) 3_566 ? C4 S1 1.739(6) . ? C5 N2 1.300(9) . ? C5 N1 1.354(8) . ? C5 H5 0.9300 . ? C6 C7 1.354(9) . ? C6 N2 1.359(9) . ? C6 H6 0.9300 . ? C7 N1 1.375(8) . ? C7 H7 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 127.4(5) . . ? C2 C1 S1 112.6(5) . . ? N1 C1 S1 119.9(5) . . ? C1 C2 C3 111.9(5) . . ? C1 C2 H2 124.1 . . ? C3 C2 H2 124.1 . . ? C4 C3 C2 114.0(6) . . ? C4 C3 H3 123.0 . . ? C2 C3 H3 123.0 . . ? C3 C4 C4 129.7(7) . 3_566 ? C3 C4 S1 110.9(4) . . ? C4 C4 S1 119.3(6) 3_566 . ? N2 C5 N1 112.9(6) . . ? N2 C5 H5 123.6 . . ? N1 C5 H5 123.6 . . ? C7 C6 N2 110.7(6) . . ? C7 C6 H6 124.6 . . ? N2 C6 H6 124.6 . . ? C6 C7 N1 105.9(6) . . ? C6 C7 H7 127.1 . . ? N1 C7 H7 127.1 . . ? C5 N1 C7 105.6(5) . . ? C5 N1 C1 126.3(5) . . ? C7 N1 C1 128.1(5) . . ? C5 N2 C6 104.9(6) . . ? C1 S1 C4 90.6(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.514 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.091 #===END data_1 _database_code_depnum_ccdc_archive 'CCDC 792211' #TrackingRef '- Four Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Ag N4 S2, N O3' _chemical_formula_sum 'C14 H10 Ag N5 O3 S2' _chemical_formula_weight 468.28 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 3.8169(14) _cell_length_b 7.901(3) _cell_length_c 26.283(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.527(6) _cell_angle_gamma 90.00 _cell_volume 787.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 956 _cell_measurement_theta_min 2.578 _cell_measurement_theta_max 23.044 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.975 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.571 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8100 _exptl_absorpt_correction_T_max 0.8587 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3757 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_av_sigmaI/netI 0.0778 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1398 _reflns_number_gt 940 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0702P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1398 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 1.5000 1.11238(11) 0.2500 0.0513(4) Uani 1 2 d S . . C1 C 0.7447(17) 0.7503(9) 0.0911(2) 0.0352(16) Uani 1 1 d . . . C2 C 0.6287(19) 0.6065(9) 0.1104(3) 0.0430(18) Uani 1 1 d . . . H2 H 0.6198 0.5877 0.1452 0.052 Uiso 1 1 calc R . . C3 C 0.5227(18) 0.4879(9) 0.0723(2) 0.0390(16) Uani 1 1 d . . . H3 H 0.4383 0.3810 0.0793 0.047 Uiso 1 1 calc R . . C4 C 0.5536(18) 0.5419(8) 0.0243(2) 0.0357(16) Uani 1 1 d . . . C5 C 1.0722(19) 0.8925(9) 0.1664(3) 0.0415(17) Uani 1 1 d . . . H5 H 1.1360 0.7952 0.1851 0.050 Uiso 1 1 calc R . . C6 C 1.0181(19) 1.1522(9) 0.1429(3) 0.0421(18) Uani 1 1 d . . . H6 H 1.0405 1.2694 0.1433 0.051 Uiso 1 1 calc R . . C7 C 0.850(2) 1.0605(9) 0.1033(3) 0.0413(18) Uani 1 1 d . . . H7 H 0.7369 1.1019 0.0726 0.050 Uiso 1 1 calc R . . N1 N 0.8830(15) 0.8937(7) 0.1184(2) 0.0366(13) Uani 1 1 d . . . N2 N 1.1494(15) 1.0460(7) 0.1820(2) 0.0378(14) Uani 1 1 d . . . N3 N 1.5000 1.5075(13) 0.2500 0.067(3) Uani 1 2 d S . . O1 O 1.370(2) 1.4322(9) 0.2116(2) 0.107(3) Uani 1 1 d . . . O2 O 1.5000 1.6616(11) 0.2500 0.120(5) Uani 1 2 d S . . S1 S 0.7285(5) 0.7441(2) 0.02552(6) 0.0378(5) 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 0.0609(6) 0.0554(6) 0.0340(5) 0.000 -0.0098(4) 0.000 C1 0.037(4) 0.037(4) 0.030(3) -0.001(3) -0.005(3) 0.003(3) C2 0.045(4) 0.053(5) 0.030(4) 0.004(3) 0.002(3) -0.002(4) C3 0.047(4) 0.034(4) 0.035(4) 0.001(3) 0.003(3) 0.001(3) C4 0.036(4) 0.033(4) 0.038(4) -0.001(3) 0.002(3) 0.003(3) C5 0.047(4) 0.043(4) 0.031(4) 0.004(3) -0.007(3) 0.002(4) C6 0.051(5) 0.036(4) 0.039(4) 0.000(3) 0.003(3) -0.001(3) C7 0.047(5) 0.035(4) 0.039(4) 0.003(3) -0.008(3) 0.003(3) N1 0.040(3) 0.037(3) 0.031(3) -0.007(3) -0.001(3) 0.003(3) N2 0.043(4) 0.037(3) 0.032(3) -0.002(3) -0.002(3) 0.000(3) N3 0.115(9) 0.045(7) 0.038(5) 0.000 0.001(5) 0.000 O1 0.175(8) 0.095(6) 0.049(4) -0.021(4) 0.008(5) -0.068(5) O2 0.194(13) 0.035(6) 0.111(9) 0.000 -0.075(8) 0.000 S1 0.0406(11) 0.0396(10) 0.0322(9) -0.0012(7) -0.0003(8) -0.0050(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.172(5) 2_855 ? Ag1 N2 2.172(5) . ? Ag1 O1 2.745(8) 2_855 ? Ag1 O1 2.745(8) . ? C1 C2 1.340(10) . ? C1 N1 1.412(8) . ? C1 S1 1.717(6) . ? C2 C3 1.398(9) . ? C2 H2 0.9300 . ? C3 C4 1.350(9) . ? C3 H3 0.9300 . ? C4 C4 1.454(13) 3_665 ? C4 S1 1.730(7) . ? C5 N2 1.303(8) . ? C5 N1 1.380(9) . ? C5 H5 0.9300 . ? C6 C7 1.367(10) . ? C6 N2 1.376(9) . ? C6 H6 0.9300 . ? C7 N1 1.377(8) . ? C7 H7 0.9300 . ? N3 O2 1.218(13) . ? N3 O1 1.227(7) 2_855 ? N3 O1 1.227(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ag1 N2 152.1(3) 2_855 . ? N2 Ag1 O1 81.4(2) 2_855 2_855 ? N2 Ag1 O1 126.4(2) . 2_855 ? N2 Ag1 O1 126.4(2) 2_855 . ? N2 Ag1 O1 81.4(2) . . ? O1 Ag1 O1 46.0(3) 2_855 . ? C2 C1 N1 127.5(6) . . ? C2 C1 S1 112.4(5) . . ? N1 C1 S1 120.1(5) . . ? C1 C2 C3 112.2(6) . . ? C1 C2 H2 123.9 . . ? C3 C2 H2 123.9 . . ? C4 C3 C2 114.2(6) . . ? C4 C3 H3 122.9 . . ? C2 C3 H3 122.9 . . ? C3 C4 C4 129.0(8) . 3_665 ? C3 C4 S1 110.4(5) . . ? C4 C4 S1 120.5(7) 3_665 . ? N2 C5 N1 110.9(6) . . ? N2 C5 H5 124.5 . . ? N1 C5 H5 124.5 . . ? C7 C6 N2 110.2(6) . . ? C7 C6 H6 124.9 . . ? N2 C6 H6 124.9 . . ? C6 C7 N1 105.6(6) . . ? C6 C7 H7 127.2 . . ? N1 C7 H7 127.2 . . ? C7 N1 C5 106.9(6) . . ? C7 N1 C1 127.2(6) . . ? C5 N1 C1 125.8(6) . . ? C5 N2 C6 106.4(6) . . ? C5 N2 Ag1 125.4(4) . . ? C6 N2 Ag1 127.3(5) . . ? O2 N3 O1 119.0(6) . 2_855 ? O2 N3 O1 119.0(6) . . ? O1 N3 O1 122.0(11) 2_855 . ? N3 O1 Ag1 96.0(6) . . ? C1 S1 C4 90.9(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.553 _refine_diff_density_min -0.752 _refine_diff_density_rms 0.160 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 792212' #TrackingRef '- Four Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Ag N4 S2, Cl O4' _chemical_formula_sum 'C14 H10 Ag Cl N4 O4 S2' _chemical_formula_weight 505.70 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 13.731(4) _cell_length_b 8.046(3) _cell_length_c 15.458(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.940(4) _cell_angle_gamma 90.00 _cell_volume 1670.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2575 _cell_measurement_theta_min 2.694 _cell_measurement_theta_max 26.881 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.010 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.646 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8022 _exptl_absorpt_correction_T_max 0.8527 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7929 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2907 _reflns_number_gt 2144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0919P)^2^+4.6764P] 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 2907 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1698 _refine_ls_wR_factor_gt 0.1600 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 O4 O -0.0204(6) 0.6763(10) 0.2824(5) 0.104(3) Uani 1 1 d . . . Cl1 Cl 0.00167(15) 0.5289(2) 0.24234(15) 0.0568(5) Uani 1 1 d . . . Ag1 Ag 1.00644(4) 1.09035(8) 0.23088(4) 0.0557(3) Uani 1 1 d . . . C12 C 0.8232(5) 0.8951(9) 0.1444(5) 0.0457(17) Uani 1 1 d . . . H12 H 0.8605 0.7993 0.1603 0.055 Uiso 1 1 calc R . . C13 C 0.7819(6) 1.1505(10) 0.1242(5) 0.0509(19) Uani 1 1 d . . . H13 H 0.7858 1.2659 0.1235 0.061 Uiso 1 1 calc R . . C14 C 0.6991(6) 1.0615(9) 0.0933(6) 0.057(2) Uani 1 1 d . . . H14 H 0.6363 1.1025 0.0682 0.068 Uiso 1 1 calc R . . C8 C 0.6659(5) 0.7539(9) 0.0907(5) 0.0429(16) Uani 1 1 d . . . C9 C 0.6740(6) 0.6153(9) 0.1394(5) 0.0487(18) Uani 1 1 d . . . H9 H 0.7218 0.6001 0.1910 0.058 Uiso 1 1 calc R . . C10 C 0.6026(5) 0.4957(9) 0.1043(5) 0.0465(17) Uani 1 1 d . . . H10 H 0.5979 0.3931 0.1309 0.056 Uiso 1 1 calc R . . C11 C 0.5402(6) 0.5436(8) 0.0271(5) 0.0425(16) Uani 1 1 d . . . C5 C 1.1938(6) 0.8966(9) 0.3172(5) 0.0493(18) Uani 1 1 d . . . H5 H 1.1782 0.8157 0.2735 0.059 Uiso 1 1 calc R . . C6 C 1.1934(6) 1.1227(9) 0.3904(6) 0.054(2) Uani 1 1 d . . . H6 H 1.1771 1.2287 0.4068 0.065 Uiso 1 1 calc R . . C7 C 1.2668(6) 1.0251(9) 0.4370(6) 0.0526(19) Uani 1 1 d . . . H7 H 1.3090 1.0506 0.4905 0.063 Uiso 1 1 calc R . . C1 C 1.3233(5) 0.7375(9) 0.4126(5) 0.0417(16) Uani 1 1 d . . . C2 C 1.2955(6) 0.5788(9) 0.3949(6) 0.054(2) Uani 1 1 d . . . H2 H 1.2330 0.5477 0.3632 0.065 Uiso 1 1 calc R . . C3 C 1.3704(6) 0.4666(10) 0.4290(5) 0.0517(19) Uani 1 1 d . . . H3 H 1.3635 0.3524 0.4205 0.062 Uiso 1 1 calc R . . C4 C 1.4538(5) 0.5375(8) 0.4756(5) 0.0423(16) Uani 1 1 d . . . N4 N 0.8590(4) 1.0471(7) 0.1565(4) 0.0447(14) Uani 1 1 d . . . N3 N 0.7266(4) 0.8958(7) 0.1064(4) 0.0419(13) Uani 1 1 d . . . N2 N 1.1471(5) 1.0403(8) 0.3152(4) 0.0504(15) Uani 1 1 d . . . N1 N 1.2658(4) 0.8810(7) 0.3888(4) 0.0423(14) Uani 1 1 d . . . O1 O -0.0794(6) 0.4737(12) 0.1792(7) 0.129(4) Uani 1 1 d . . . O2 O 0.0328(12) 0.4144(13) 0.3054(11) 0.206(7) Uani 1 1 d . . . O3 O 0.0773(8) 0.5627(18) 0.2009(9) 0.188(7) Uani 1 1 d . . . S1 S 1.44360(14) 0.7526(2) 0.47380(15) 0.0530(5) Uani 1 1 d . . . S2 S 0.57202(14) 0.7417(2) -0.00264(13) 0.0471(5) 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 O4 0.134(7) 0.084(5) 0.091(5) -0.025(4) 0.016(5) 0.031(5) Cl1 0.0526(11) 0.0371(10) 0.0775(14) -0.0096(9) 0.0061(10) 0.0021(8) Ag1 0.0436(4) 0.0552(4) 0.0625(5) 0.0019(3) -0.0028(3) -0.0031(3) C12 0.046(4) 0.044(4) 0.045(4) 0.001(3) 0.005(3) 0.006(3) C13 0.050(4) 0.036(4) 0.062(5) 0.003(3) 0.000(4) -0.003(3) C14 0.047(4) 0.042(4) 0.076(6) 0.005(4) 0.002(4) 0.009(4) C8 0.040(4) 0.047(4) 0.041(4) -0.002(3) 0.006(3) 0.002(3) C9 0.052(4) 0.047(4) 0.043(4) 0.001(3) 0.001(3) -0.006(3) C10 0.053(4) 0.039(4) 0.045(4) 0.004(3) 0.004(3) -0.001(3) C11 0.053(4) 0.034(4) 0.044(4) -0.005(3) 0.017(3) -0.007(3) C5 0.053(4) 0.042(4) 0.049(4) -0.001(3) -0.001(3) 0.002(3) C6 0.051(4) 0.039(4) 0.067(5) -0.007(4) -0.002(4) 0.000(3) C7 0.053(5) 0.040(4) 0.060(5) -0.008(4) 0.002(4) -0.006(3) C1 0.037(4) 0.043(4) 0.044(4) 0.004(3) 0.008(3) -0.002(3) C2 0.050(4) 0.041(4) 0.064(5) -0.005(4) -0.003(4) -0.005(4) C3 0.051(4) 0.041(4) 0.060(5) 0.005(3) 0.004(4) -0.001(3) C4 0.047(4) 0.025(3) 0.056(4) 0.002(3) 0.015(3) -0.005(3) N4 0.045(3) 0.041(3) 0.045(3) -0.002(3) 0.002(3) -0.001(3) N3 0.041(3) 0.034(3) 0.048(3) -0.002(3) 0.003(3) -0.001(3) N2 0.047(4) 0.045(4) 0.057(4) 0.000(3) 0.005(3) 0.004(3) N1 0.041(3) 0.038(3) 0.048(4) 0.002(3) 0.008(3) 0.000(3) O1 0.081(5) 0.111(6) 0.176(10) -0.056(7) -0.013(6) -0.023(5) O2 0.250(15) 0.087(7) 0.231(15) 0.048(8) -0.066(13) 0.013(8) O3 0.116(8) 0.282(16) 0.186(12) -0.139(12) 0.074(8) -0.086(9) S1 0.0438(10) 0.0343(10) 0.0747(14) 0.0057(9) -0.0021(9) -0.0042(8) S2 0.0450(10) 0.0386(10) 0.0519(11) 0.0030(8) -0.0030(8) -0.0020(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 Cl1 1.400(8) . ? Cl1 O3 1.356(11) . ? Cl1 O2 1.346(12) . ? Cl1 O1 1.393(8) . ? Ag1 N4 2.140(6) . ? Ag1 N2 2.134(6) . ? C12 N4 1.317(9) . ? C12 N3 1.335(9) . ? C12 H12 0.9300 . ? C13 C14 1.345(11) . ? C13 N4 1.357(10) . ? C13 H13 0.9300 . ? C14 N3 1.389(9) . ? C14 H14 0.9300 . ? C8 C9 1.338(10) . ? C8 N3 1.405(9) . ? C8 S2 1.727(7) . ? C9 C10 1.400(10) . ? C9 H9 0.9300 . ? C10 C11 1.373(10) . ? C10 H10 0.9300 . ? C11 C11 1.425(14) 3_665 ? C11 S2 1.739(7) . ? C5 N2 1.319(9) . ? C5 N1 1.329(9) . ? C5 H5 0.9300 . ? C6 N2 1.374(10) . ? C6 C7 1.360(11) . ? C6 H6 0.9300 . ? C7 N1 1.376(9) . ? C7 H7 0.9300 . ? C1 C2 1.344(10) . ? C1 N1 1.404(9) . ? C1 S1 1.730(7) . ? C2 C3 1.388(11) . ? C2 H2 0.9300 . ? C3 C4 1.347(11) . ? C3 H3 0.9300 . ? C4 C4 1.464(14) 3_866 ? C4 S1 1.736(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cl1 O2 108.7(10) . . ? O3 Cl1 O1 108.2(7) . . ? O2 Cl1 O1 112.2(7) . . ? O3 Cl1 O4 107.2(6) . . ? O2 Cl1 O4 109.0(8) . . ? O1 Cl1 O4 111.4(5) . . ? N4 Ag1 N2 159.1(2) . . ? N4 C12 N3 111.5(6) . . ? N4 C12 H12 124.3 . . ? N3 C12 H12 124.3 . . ? C14 C13 N4 110.0(7) . . ? C14 C13 H13 125.0 . . ? N4 C13 H13 125.0 . . ? C13 C14 N3 106.0(7) . . ? C13 C14 H14 127.0 . . ? N3 C14 H14 127.0 . . ? C9 C8 N3 127.1(7) . . ? C9 C8 S2 112.6(6) . . ? N3 C8 S2 120.3(5) . . ? C8 C9 C10 112.6(7) . . ? C8 C9 H9 123.7 . . ? C10 C9 H9 123.7 . . ? C11 C10 C9 113.9(7) . . ? C11 C10 H10 123.1 . . ? C9 C10 H10 123.1 . . ? C10 C11 C11 129.9(8) . 3_665 ? C10 C11 S2 110.0(5) . . ? C11 C11 S2 120.2(7) 3_665 . ? N2 C5 N1 112.1(7) . . ? N2 C5 H5 124.0 . . ? N1 C5 H5 124.0 . . ? N2 C6 C7 109.3(7) . . ? N2 C6 H6 125.3 . . ? C7 C6 H6 125.3 . . ? C6 C7 N1 106.1(7) . . ? C6 C7 H7 127.0 . . ? N1 C7 H7 127.0 . . ? C2 C1 N1 127.4(7) . . ? C2 C1 S1 112.1(6) . . ? N1 C1 S1 120.5(5) . . ? C1 C2 C3 112.6(7) . . ? C1 C2 H2 123.7 . . ? C3 C2 H2 123.7 . . ? C4 C3 C2 114.1(7) . . ? C4 C3 H3 122.9 . . ? C2 C3 H3 122.9 . . ? C3 C4 C4 130.6(8) . 3_866 ? C3 C4 S1 110.9(6) . . ? C4 C4 S1 118.5(7) 3_866 . ? C12 N4 C13 106.1(6) . . ? C12 N4 Ag1 120.7(5) . . ? C13 N4 Ag1 132.6(5) . . ? C12 N3 C14 106.5(6) . . ? C12 N3 C8 124.9(6) . . ? C14 N3 C8 128.4(6) . . ? C5 N2 C6 105.4(6) . . ? C5 N2 Ag1 123.6(5) . . ? C6 N2 Ag1 128.8(5) . . ? C5 N1 C7 107.1(6) . . ? C5 N1 C1 125.2(6) . . ? C7 N1 C1 127.5(6) . . ? C1 S1 C4 90.2(4) . . ? C8 S2 C11 90.9(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.888 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.132 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 792213' #TrackingRef '- Four Cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Ag N4 S2, C2 F3 O2' _chemical_formula_sum 'C16 H10 Ag F3 N4 O2 S2' _chemical_formula_weight 519.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M ' P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2588(12) _cell_length_b 9.6887(14) _cell_length_c 13.0447(19) _cell_angle_alpha 71.193(2) _cell_angle_beta 81.694(2) _cell_angle_gamma 72.739(2) _cell_volume 942.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2076 _cell_measurement_theta_min 2.305 _cell_measurement_theta_max 27.812 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.830 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 1.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8142 _exptl_absorpt_correction_T_max 0.8777 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4374 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3231 _reflns_number_gt 2492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0858P)^2^+0.3911P] 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 3231 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1489 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 1.35393(5) 0.58802(5) -0.07189(4) 0.0840(3) Uani 1 1 d . . . C9 C 1.1653(6) 0.3636(6) 0.0842(4) 0.0563(12) Uani 1 1 d . . . H9 H 1.1724 0.3993 0.1411 0.068 Uiso 1 1 calc R . . C11 C 1.1084(9) 0.2340(7) -0.0060(5) 0.0788(17) Uani 1 1 d . . . H11 H 1.0700 0.1652 -0.0254 0.095 Uiso 1 1 calc R . . C10 C 1.1907(9) 0.3326(7) -0.0710(5) 0.0797(18) Uani 1 1 d . . . H10 H 1.2194 0.3432 -0.1442 0.096 Uiso 1 1 calc R . . C1 C 1.0130(6) 0.1758(5) 0.1894(4) 0.0517(11) Uani 1 1 d . . . C2 C 1.0170(7) 0.0277(6) 0.2244(4) 0.0634(13) Uani 1 1 d . . . H2 H 1.0774 -0.0426 0.1887 0.076 Uiso 1 1 calc R . . C3 C 0.9182(7) -0.0068(6) 0.3218(4) 0.0627(14) Uani 1 1 d . . . H3 H 0.9056 -0.1036 0.3567 0.075 Uiso 1 1 calc R . . C4 C 0.8425(6) 0.1125(5) 0.3609(4) 0.0485(11) Uani 1 1 d . . . C5 C 0.7371(6) 0.1175(6) 0.4587(4) 0.0502(11) Uani 1 1 d . . . C6 C 0.6359(9) 0.2368(6) 0.4867(5) 0.0723(16) Uani 1 1 d . . . H6 H 0.6228 0.3360 0.4428 0.087 Uiso 1 1 calc R . . C7 C 0.5503(8) 0.1978(6) 0.5897(4) 0.0701(15) Uani 1 1 d . . . H7 H 0.4762 0.2680 0.6211 0.084 Uiso 1 1 calc R . . C8 C 0.5885(6) 0.0485(6) 0.6366(4) 0.0539(12) Uani 1 1 d . . . C12 C 0.4949(6) -0.1684(6) 0.7625(4) 0.0543(12) Uani 1 1 d . . . H12 H 0.5136 -0.2251 0.7143 0.065 Uiso 1 1 calc R . . C13 C 0.4271(8) -0.0967(8) 0.9056(5) 0.0775(17) Uani 1 1 d . . . H13 H 0.3877 -0.0950 0.9758 0.093 Uiso 1 1 calc R . . C14 C 0.4852(9) 0.0124(8) 0.8305(5) 0.0776(17) Uani 1 1 d . . . H14 H 0.4956 0.1008 0.8394 0.093 Uiso 1 1 calc R . . C15 C 0.3296(11) 0.6075(8) 0.2211(6) 0.090(2) Uani 1 1 d . . . C16 C 0.2091(10) 0.5650(8) 0.3124(7) 0.086(2) Uani 1 1 d . . . F1 F 0.0479(10) 0.6431(10) 0.2886(8) 0.210(4) Uani 1 1 d . . . F2 F 0.2099(12) 0.5997(12) 0.3924(5) 0.246(6) Uani 1 1 d . . . F3 F 0.1863(9) 0.4348(6) 0.3336(5) 0.169(3) Uani 1 1 d . . . N2 N 1.2260(5) 0.4144(5) -0.0149(4) 0.0622(12) Uani 1 1 d . . . N1 N 1.0918(5) 0.2540(5) 0.0937(3) 0.0542(10) Uani 1 1 d . . . N3 N 0.5259(5) -0.0317(5) 0.7385(3) 0.0575(10) Uani 1 1 d . . . N4 N 0.4345(5) -0.2103(6) 0.8634(3) 0.0631(12) Uani 1 1 d . . . O1 O 0.2919(10) 0.7265(8) 0.1531(6) 0.164(3) Uani 1 1 d . . . O2 O 0.4641(13) 0.5255(10) 0.2332(8) 0.251(7) Uani 1 1 d . . . S1 S 0.89046(16) 0.27419(14) 0.27486(10) 0.0511(3) Uani 1 1 d . . . S2 S 0.72872(16) -0.04889(14) 0.55770(10) 0.0572(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0572(3) 0.0902(4) 0.0756(4) 0.0319(3) -0.0082(2) -0.0368(3) C9 0.049(3) 0.066(3) 0.046(3) 0.004(2) -0.002(2) -0.026(2) C11 0.109(5) 0.073(4) 0.054(3) -0.017(3) 0.016(3) -0.035(4) C10 0.102(5) 0.077(4) 0.049(3) -0.012(3) 0.020(3) -0.025(4) C1 0.051(3) 0.056(3) 0.041(2) 0.003(2) -0.004(2) -0.023(2) C2 0.072(3) 0.053(3) 0.059(3) -0.008(3) 0.008(3) -0.023(3) C3 0.069(3) 0.048(3) 0.062(3) 0.003(3) 0.004(3) -0.029(3) C4 0.047(2) 0.049(3) 0.044(2) 0.005(2) -0.008(2) -0.022(2) C5 0.053(3) 0.056(3) 0.040(2) 0.000(2) -0.006(2) -0.026(2) C6 0.105(5) 0.052(3) 0.055(3) -0.003(3) 0.012(3) -0.037(3) C7 0.097(4) 0.055(3) 0.055(3) -0.012(3) 0.015(3) -0.028(3) C8 0.057(3) 0.066(3) 0.038(2) -0.003(2) -0.004(2) -0.029(2) C12 0.053(3) 0.067(3) 0.040(2) 0.002(2) -0.003(2) -0.030(2) C13 0.080(4) 0.106(5) 0.047(3) -0.012(3) 0.007(3) -0.040(4) C14 0.100(5) 0.094(4) 0.049(3) -0.021(3) 0.013(3) -0.048(4) C15 0.114(6) 0.058(4) 0.095(5) -0.028(4) 0.043(4) -0.032(4) C16 0.092(5) 0.078(4) 0.105(5) -0.050(4) 0.029(4) -0.039(4) F1 0.143(6) 0.215(8) 0.226(9) -0.033(6) 0.069(6) -0.053(6) F2 0.301(10) 0.466(14) 0.133(5) -0.193(8) 0.126(6) -0.291(11) F3 0.224(7) 0.101(4) 0.189(6) -0.049(4) 0.093(5) -0.097(4) N2 0.049(2) 0.065(3) 0.050(2) 0.011(2) 0.0042(19) -0.017(2) N1 0.052(2) 0.055(2) 0.046(2) -0.0003(19) 0.0047(18) -0.0198(19) N3 0.060(2) 0.074(3) 0.039(2) -0.004(2) -0.0002(18) -0.035(2) N4 0.056(3) 0.084(3) 0.041(2) 0.006(2) -0.0029(18) -0.033(2) O1 0.158(6) 0.135(6) 0.120(5) 0.024(4) 0.048(5) -0.018(5) O2 0.195(8) 0.151(7) 0.227(10) 0.040(6) 0.131(8) 0.044(6) S1 0.0551(7) 0.0499(7) 0.0428(6) 0.0014(5) 0.0007(5) -0.0243(5) S2 0.0566(7) 0.0549(7) 0.0462(7) 0.0077(6) 0.0007(5) -0.0212(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 N4 2.126(5) 1_664 ? Ag1 N2 2.126(4) . ? Ag1 O2 2.738(9) 2_765 ? Ag1 Ag1 3.0084(9) 2_865 ? C9 N2 1.310(6) . ? C9 N1 1.336(6) . ? C9 H9 0.9300 . ? C11 C10 1.338(8) . ? C11 N1 1.358(7) . ? C11 H11 0.9300 . ? C10 N2 1.349(8) . ? C10 H10 0.9300 . ? C1 C2 1.350(7) . ? C1 N1 1.416(6) . ? C1 S1 1.721(5) . ? C2 C3 1.408(7) . ? C2 H2 0.9300 . ? C3 C4 1.359(7) . ? C3 H3 0.9300 . ? C4 C5 1.443(7) . ? C4 S1 1.726(4) . ? C5 C6 1.333(8) . ? C5 S2 1.723(5) . ? C6 C7 1.417(8) . ? C6 H6 0.9300 . ? C7 C8 1.334(7) . ? C7 H7 0.9300 . ? C8 N3 1.418(6) . ? C8 S2 1.711(5) . ? C12 N4 1.316(6) . ? C12 N3 1.352(6) . ? C12 H12 0.9300 . ? C13 C14 1.344(8) . ? C13 N4 1.364(8) . ? C13 H13 0.9300 . ? C14 N3 1.365(7) . ? C14 H14 0.9300 . ? C15 O2 1.156(11) . ? C15 O1 1.191(9) . ? C15 C16 1.471(9) . ? C16 F2 1.196(8) . ? C16 F3 1.267(7) . ? C16 F1 1.346(11) . ? N4 Ag1 2.126(5) 1_446 ? O2 Ag1 2.738(9) 2_765 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ag1 N2 168.96(16) 1_664 . ? N4 Ag1 O2 91.3(3) 1_664 2_765 ? N2 Ag1 O2 93.4(3) . 2_765 ? N4 Ag1 Ag1 96.42(12) 1_664 2_865 ? N2 Ag1 Ag1 93.67(11) . 2_865 ? O2 Ag1 Ag1 88.8(3) 2_765 2_865 ? N2 C9 N1 111.7(5) . . ? N2 C9 H9 124.1 . . ? N1 C9 H9 124.1 . . ? C10 C11 N1 106.6(5) . . ? C10 C11 H11 126.7 . . ? N1 C11 H11 126.7 . . ? C11 C10 N2 110.2(5) . . ? C11 C10 H10 124.9 . . ? N2 C10 H10 124.9 . . ? C2 C1 N1 128.1(5) . . ? C2 C1 S1 112.5(4) . . ? N1 C1 S1 119.4(4) . . ? C1 C2 C3 111.3(5) . . ? C1 C2 H2 124.3 . . ? C3 C2 H2 124.3 . . ? C4 C3 C2 114.6(5) . . ? C4 C3 H3 122.7 . . ? C2 C3 H3 122.7 . . ? C3 C4 C5 129.5(4) . . ? C3 C4 S1 110.1(4) . . ? C5 C4 S1 120.4(4) . . ? C6 C5 C4 129.3(5) . . ? C6 C5 S2 111.1(4) . . ? C4 C5 S2 119.6(4) . . ? C5 C6 C7 113.5(5) . . ? C5 C6 H6 123.3 . . ? C7 C6 H6 123.3 . . ? C8 C7 C6 112.1(5) . . ? C8 C7 H7 123.9 . . ? C6 C7 H7 123.9 . . ? C7 C8 N3 128.0(5) . . ? C7 C8 S2 112.2(4) . . ? N3 C8 S2 119.7(4) . . ? N4 C12 N3 110.7(5) . . ? N4 C12 H12 124.6 . . ? N3 C12 H12 124.6 . . ? C14 C13 N4 109.8(5) . . ? C14 C13 H13 125.1 . . ? N4 C13 H13 125.1 . . ? C13 C14 N3 106.6(5) . . ? C13 C14 H14 126.7 . . ? N3 C14 H14 126.7 . . ? O2 C15 O1 126.1(8) . . ? O2 C15 C16 112.4(8) . . ? O1 C15 C16 120.5(8) . . ? F2 C16 F3 112.6(8) . . ? F2 C16 F1 96.8(8) . . ? F3 C16 F1 96.2(7) . . ? F2 C16 C15 118.5(6) . . ? F3 C16 C15 116.7(6) . . ? F1 C16 C15 111.6(8) . . ? C9 N2 C10 105.2(5) . . ? C9 N2 Ag1 126.4(4) . . ? C10 N2 Ag1 128.3(4) . . ? C9 N1 C11 106.2(5) . . ? C9 N1 C1 126.1(4) . . ? C11 N1 C1 127.6(5) . . ? C12 N3 C14 106.8(4) . . ? C12 N3 C8 125.8(4) . . ? C14 N3 C8 127.4(4) . . ? C12 N4 C13 106.1(5) . . ? C12 N4 Ag1 121.9(4) . 1_446 ? C13 N4 Ag1 131.9(4) . 1_446 ? C15 O2 Ag1 121.9(9) . 2_765 ? C1 S1 C4 91.4(2) . . ? C8 S2 C5 91.1(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.073 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.086 #===END