# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Wiley Youngs' _publ_contact_author_email youngs@uakron.edu loop_ _publ_author_name 'Wiley Youngs' B.Wright data_bw1 _database_code_depnum_ccdc_archive 'CCDC 845904' #TrackingRef '- bw cpd 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9 Cl4 N2 O, I' _chemical_formula_sum 'C10 H9 Cl4 I N2 O' _chemical_formula_weight 441.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2405(9) _cell_length_b 6.9153(7) _cell_length_c 22.244(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.331(2) _cell_angle_gamma 90.00 _cell_volume 1402.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7172 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.22 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 3.033 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6324 _exptl_absorpt_correction_T_max 0.7934 _exptl_absorpt_process_details 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 'CCD Area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11737 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3346 _reflns_number_gt 3154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+1.5375P] 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 3346 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0639 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 I1 I 0.118777(18) 0.17983(2) 0.319777(7) 0.02068(7) Uani 1 1 d . . . Cl1 Cl 0.60582(6) 0.72308(9) 0.43637(3) 0.02119(13) Uani 1 1 d . . . Cl2 Cl 0.56815(7) 0.77947(9) 0.57113(3) 0.02173(13) Uani 1 1 d . . . Cl3 Cl 0.25871(8) 0.78399(10) 0.60804(3) 0.02531(14) Uani 1 1 d . . . Cl4 Cl -0.02111(7) 0.75189(9) 0.51070(3) 0.02180(13) Uani 1 1 d . . . O1 O 0.3440(2) 0.9084(3) 0.24149(9) 0.0285(4) Uani 1 1 d . . . H1 H 0.2917 0.9791 0.2599 0.043 Uiso 1 1 calc R . . N1 N 0.2865(2) 0.6728(3) 0.34993(10) 0.0149(4) Uani 1 1 d . . . N2 N 0.0682(2) 0.6946(3) 0.37535(10) 0.0154(4) Uani 1 1 d . . . C1 C 0.1425(3) 0.6679(3) 0.32988(12) 0.0163(5) Uani 1 1 d . . . H1A H 0.0991 0.6480 0.2886 0.020 Uiso 1 1 calc R . . C2 C 0.1676(3) 0.7192(3) 0.42853(11) 0.0152(5) Uani 1 1 d . . . C3 C 0.3077(3) 0.7064(3) 0.41216(11) 0.0148(5) Uani 1 1 d . . . C4 C 0.4329(3) 0.7277(3) 0.45579(11) 0.0165(5) Uani 1 1 d . . . C5 C 0.4155(3) 0.7551(3) 0.51584(11) 0.0171(5) Uani 1 1 d . . . C6 C 0.2748(3) 0.7625(4) 0.53238(11) 0.0182(5) Uani 1 1 d . . . C7 C 0.1496(3) 0.7453(3) 0.48919(11) 0.0164(5) Uani 1 1 d . . . C8 C -0.0928(3) 0.7041(4) 0.36562(13) 0.0230(5) Uani 1 1 d . . . H8A H -0.1306 0.6954 0.3219 0.034 Uiso 1 1 calc R . . H8B H -0.1237 0.8269 0.3815 0.034 Uiso 1 1 calc R . . H8C H -0.1313 0.5965 0.3869 0.034 Uiso 1 1 calc R . . C9 C 0.3951(3) 0.6328(4) 0.30945(12) 0.0197(5) Uani 1 1 d . . . H9A H 0.3491 0.5508 0.2751 0.024 Uiso 1 1 calc R . . H9B H 0.4784 0.5599 0.3324 0.024 Uiso 1 1 calc R . . C10 C 0.4523(3) 0.8160(4) 0.28442(13) 0.0230(5) Uani 1 1 d . . . H10A H 0.4855 0.9061 0.3185 0.028 Uiso 1 1 calc R . . H10B H 0.5379 0.7842 0.2647 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02357(10) 0.01646(10) 0.02060(10) -0.00055(6) -0.00067(7) 0.00045(6) Cl1 0.0136(3) 0.0226(3) 0.0277(3) 0.0021(2) 0.0043(2) 0.0001(2) Cl2 0.0229(3) 0.0187(3) 0.0212(3) 0.0012(2) -0.0037(2) -0.0014(2) Cl3 0.0346(3) 0.0258(3) 0.0167(3) -0.0022(2) 0.0078(3) -0.0049(3) Cl4 0.0209(3) 0.0203(3) 0.0271(3) -0.0009(2) 0.0125(2) -0.0002(2) O1 0.0323(10) 0.0311(11) 0.0241(10) 0.0073(8) 0.0104(8) 0.0065(9) N1 0.0142(9) 0.0146(10) 0.0166(10) -0.0009(7) 0.0042(8) -0.0006(7) N2 0.0153(10) 0.0135(10) 0.0173(10) 0.0003(7) 0.0024(8) -0.0009(7) C1 0.0192(11) 0.0127(11) 0.0170(11) 0.0005(8) 0.0028(9) 0.0007(9) C2 0.0132(11) 0.0119(10) 0.0205(12) 0.0004(9) 0.0031(9) 0.0003(8) C3 0.0181(11) 0.0103(10) 0.0168(11) 0.0006(8) 0.0054(9) 0.0000(9) C4 0.0159(11) 0.0139(11) 0.0205(12) 0.0008(9) 0.0052(9) 0.0014(9) C5 0.0202(12) 0.0119(11) 0.0182(12) 0.0007(9) -0.0003(9) -0.0007(9) C6 0.0254(12) 0.0132(11) 0.0166(12) -0.0006(9) 0.0056(10) -0.0010(10) C7 0.0192(11) 0.0112(11) 0.0204(12) 0.0009(9) 0.0080(9) 0.0002(9) C8 0.0138(11) 0.0292(14) 0.0258(13) -0.0003(11) 0.0031(10) -0.0010(10) C9 0.0196(11) 0.0209(12) 0.0206(12) -0.0012(10) 0.0094(10) 0.0007(10) C10 0.0228(12) 0.0228(14) 0.0259(14) 0.0044(10) 0.0110(11) 0.0005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.722(2) . ? Cl2 C5 1.723(3) . ? Cl3 C6 1.720(3) . ? Cl4 C7 1.721(2) . ? O1 C10 1.418(3) . ? N1 C1 1.333(3) . ? N1 C3 1.386(3) . ? N1 C9 1.479(3) . ? N2 C1 1.324(3) . ? N2 C2 1.385(3) . ? N2 C8 1.469(3) . ? C2 C7 1.398(3) . ? C2 C3 1.404(3) . ? C3 C4 1.392(4) . ? C4 C5 1.384(3) . ? C5 C6 1.409(4) . ? C6 C7 1.384(4) . ? C9 C10 1.513(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C3 108.1(2) . . ? C1 N1 C9 122.0(2) . . ? C3 N1 C9 129.7(2) . . ? C1 N2 C2 108.4(2) . . ? C1 N2 C8 122.1(2) . . ? C2 N2 C8 129.4(2) . . ? N2 C1 N1 110.7(2) . . ? N2 C2 C7 132.4(2) . . ? N2 C2 C3 106.4(2) . . ? C7 C2 C3 121.2(2) . . ? N1 C3 C4 133.0(2) . . ? N1 C3 C2 106.4(2) . . ? C4 C3 C2 120.7(2) . . ? C5 C4 C3 118.3(2) . . ? C5 C4 Cl1 120.18(19) . . ? C3 C4 Cl1 121.54(19) . . ? C4 C5 C6 120.9(2) . . ? C4 C5 Cl2 119.50(19) . . ? C6 C5 Cl2 119.57(19) . . ? C7 C6 C5 121.2(2) . . ? C7 C6 Cl3 119.46(19) . . ? C5 C6 Cl3 119.25(19) . . ? C6 C7 C2 117.7(2) . . ? C6 C7 Cl4 120.35(19) . . ? C2 C7 Cl4 121.98(19) . . ? N1 C9 C10 112.3(2) . . ? O1 C10 C9 112.0(2) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 1.955 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.108 # Attachment '- bw cpd 5.cif' data_bw2 _database_code_depnum_ccdc_archive 'CCDC 845905' #TrackingRef '- bw cpd 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H10 Cl4 N2' _chemical_formula_sum 'C18 H10 Cl4 N2' _chemical_formula_weight 396.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.979(5) _cell_length_b 12.523(13) _cell_length_c 13.184(13) _cell_angle_alpha 84.139(16) _cell_angle_beta 87.926(16) _cell_angle_gamma 83.410(16) _cell_volume 812.1(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2178 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.55 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7729 _exptl_absorpt_correction_T_max 0.9520 _exptl_absorpt_process_details 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6080 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.30 _reflns_number_total 3170 _reflns_number_gt 2215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0914P)^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 3170 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.002 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 Cl1 Cl 0.17638(18) 0.17961(8) 0.90724(7) 0.0327(3) Uani 1 1 d . . . Cl2 Cl 0.21324(18) 0.01819(8) 1.10198(7) 0.0331(3) Uani 1 1 d . . . Cl3 Cl 0.59118(19) 0.04523(8) 1.27840(7) 0.0346(3) Uani 1 1 d . . . Cl4 Cl 0.91900(18) 0.24842(9) 1.26794(6) 0.0333(3) Uani 1 1 d . . . N1 N 0.5764(6) 0.3697(3) 0.9268(2) 0.0269(7) Uani 1 1 d . . . N2 N 0.8411(6) 0.3891(3) 1.0587(2) 0.0279(7) Uani 1 1 d . . . C1 C 0.5370(6) 0.2850(3) 0.9997(3) 0.0241(8) Uani 1 1 d . . . C2 C 0.3821(7) 0.1988(3) 1.0057(3) 0.0268(8) Uani 1 1 d . . . C3 C 0.3998(7) 0.1268(3) 1.0929(3) 0.0272(8) Uani 1 1 d . . . C4 C 0.5666(7) 0.1409(3) 1.1743(3) 0.0271(8) Uani 1 1 d . . . C5 C 0.7160(7) 0.2274(3) 1.1693(3) 0.0271(8) Uani 1 1 d . . . C6 C 0.7033(7) 0.2999(3) 1.0817(3) 0.0255(8) Uani 1 1 d . . . C7 C 0.7590(7) 0.4275(3) 0.9667(3) 0.0290(8) Uani 1 1 d . . . H7 H 0.8210 0.4901 0.9309 0.035 Uiso 1 1 calc R . . C8 C 0.4660(7) 0.3974(3) 0.8239(3) 0.0320(9) Uani 1 1 d . . . H8A H 0.3961 0.4750 0.8155 0.038 Uiso 1 1 calc R . . H8B H 0.3133 0.3550 0.8162 0.038 Uiso 1 1 calc R . . C9 C 0.6796(7) 0.3743(3) 0.7421(3) 0.0314(9) Uani 1 1 d . . . C10 C 0.7317(7) 0.2749(4) 0.7086(3) 0.0369(10) Uani 1 1 d . . . H10 H 0.6305 0.2185 0.7363 0.044 Uiso 1 1 calc R . . C11 C 0.9386(8) 0.2537(4) 0.6315(3) 0.0364(10) Uani 1 1 d . . . C12 C 0.9914(8) 0.1526(4) 0.5944(3) 0.0422(11) Uani 1 1 d . . . H12 H 0.8919 0.0951 0.6204 0.051 Uiso 1 1 calc R . . C13 C 1.1883(8) 0.1370(4) 0.5199(3) 0.0451(11) Uani 1 1 d . . . H13 H 1.2230 0.0680 0.4951 0.054 Uiso 1 1 calc R . . C14 C 1.3398(8) 0.2199(4) 0.4795(3) 0.0427(11) Uani 1 1 d . . . H14 H 1.4751 0.2069 0.4281 0.051 Uiso 1 1 calc R . . C15 C 1.2917(8) 0.3190(4) 0.5142(3) 0.0456(11) Uani 1 1 d . . . H15 H 1.3956 0.3749 0.4874 0.055 Uiso 1 1 calc R . . C16 C 1.0837(8) 0.3404(4) 0.5917(3) 0.0348(10) Uani 1 1 d . . . C17 C 1.0263(8) 0.4420(4) 0.6272(3) 0.0414(11) Uani 1 1 d . . . H17 H 1.1261 0.4994 0.6007 0.050 Uiso 1 1 calc R . . C18 C 0.8272(8) 0.4596(4) 0.6998(3) 0.0404(10) Uani 1 1 d . . . H18 H 0.7872 0.5295 0.7223 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0299(5) 0.0392(6) 0.0313(5) -0.0119(4) -0.0094(4) -0.0030(4) Cl2 0.0305(5) 0.0328(6) 0.0377(5) -0.0098(4) -0.0025(4) -0.0046(4) Cl3 0.0384(5) 0.0372(6) 0.0277(5) -0.0029(4) -0.0033(4) -0.0017(4) Cl4 0.0328(5) 0.0445(7) 0.0242(5) -0.0098(4) -0.0080(3) -0.0031(4) N1 0.0277(15) 0.0298(19) 0.0238(15) -0.0069(14) -0.0046(12) -0.0004(13) N2 0.0273(15) 0.0304(19) 0.0270(16) -0.0084(14) -0.0033(12) -0.0013(13) C1 0.0223(16) 0.026(2) 0.0240(17) -0.0067(15) -0.0038(13) 0.0023(14) C2 0.0212(17) 0.034(2) 0.0271(18) -0.0138(17) -0.0049(14) 0.0022(15) C3 0.0228(17) 0.029(2) 0.0293(19) -0.0106(17) -0.0003(14) 0.0061(15) C4 0.0234(17) 0.033(2) 0.0246(18) -0.0054(16) -0.0004(14) 0.0017(16) C5 0.0223(17) 0.034(2) 0.0254(18) -0.0129(16) -0.0056(14) 0.0052(15) C6 0.0221(17) 0.031(2) 0.0238(17) -0.0126(16) -0.0025(13) 0.0031(15) C7 0.0295(18) 0.032(2) 0.0270(18) -0.0086(17) -0.0031(14) -0.0026(16) C8 0.0302(19) 0.042(3) 0.0244(18) -0.0074(17) -0.0092(15) 0.0018(17) C9 0.0294(19) 0.040(3) 0.0237(18) -0.0042(17) -0.0076(14) 0.0027(17) C10 0.032(2) 0.050(3) 0.029(2) -0.0079(19) -0.0097(16) 0.0008(18) C11 0.036(2) 0.045(3) 0.028(2) -0.0046(19) -0.0133(16) 0.0010(19) C12 0.043(2) 0.048(3) 0.034(2) -0.009(2) -0.0095(18) 0.006(2) C13 0.045(2) 0.058(3) 0.030(2) -0.008(2) -0.0056(18) 0.011(2) C14 0.036(2) 0.066(3) 0.0249(19) -0.012(2) -0.0051(16) 0.011(2) C15 0.040(2) 0.062(3) 0.034(2) -0.002(2) -0.0130(18) -0.001(2) C16 0.034(2) 0.047(3) 0.0235(18) -0.0069(18) -0.0121(15) 0.0020(18) C17 0.042(2) 0.049(3) 0.033(2) -0.003(2) -0.0105(18) -0.006(2) C18 0.040(2) 0.051(3) 0.030(2) -0.007(2) -0.0117(17) 0.001(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 Cl1 C2 1.735(4) . ? Cl2 C3 1.725(4) . ? Cl3 C4 1.725(4) . ? Cl4 C5 1.735(4) . ? N1 C7 1.375(5) . ? N1 C1 1.384(5) . ? N1 C8 1.475(4) . ? N2 C7 1.320(5) . ? N2 C6 1.380(5) . ? C1 C2 1.391(5) . ? C1 C6 1.425(5) . ? C2 C3 1.386(5) . ? C3 C4 1.418(5) . ? C4 C5 1.377(5) . ? C5 C6 1.393(5) . ? C8 C9 1.513(5) . ? C9 C10 1.357(6) . ? C9 C18 1.421(6) . ? C10 C11 1.443(5) . ? C11 C12 1.397(6) . ? C11 C16 1.418(6) . ? C12 C13 1.374(5) . ? C13 C14 1.404(7) . ? C14 C15 1.359(7) . ? C15 C16 1.451(6) . ? C16 C17 1.396(6) . ? C17 C18 1.369(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 C7 N1 C1 106.1(3) . . ? C7 N1 C8 123.1(3) . . ? C1 N1 C8 130.8(3) . . ? C7 N2 C6 103.7(3) . . ? N1 C1 C2 134.5(3) . . ? N1 C1 C6 104.6(3) . . ? C2 C1 C6 121.0(3) . . ? C3 C2 C1 117.8(3) . . ? C3 C2 Cl1 120.4(3) . . ? C1 C2 Cl1 121.8(3) . . ? C2 C3 C4 121.4(4) . . ? C2 C3 Cl2 118.9(3) . . ? C4 C3 Cl2 119.7(3) . . ? C5 C4 C3 120.8(3) . . ? C5 C4 Cl3 120.0(3) . . ? C3 C4 Cl3 119.1(3) . . ? C4 C5 C6 118.6(3) . . ? C4 C5 Cl4 122.2(3) . . ? C6 C5 Cl4 119.2(3) . . ? N2 C6 C5 128.6(3) . . ? N2 C6 C1 111.0(3) . . ? C5 C6 C1 120.4(3) . . ? N2 C7 N1 114.6(4) . . ? N1 C8 C9 111.3(3) . . ? C10 C9 C18 119.9(4) . . ? C10 C9 C8 121.6(4) . . ? C18 C9 C8 118.5(4) . . ? C9 C10 C11 120.9(4) . . ? C12 C11 C16 120.4(4) . . ? C12 C11 C10 121.9(4) . . ? C16 C11 C10 117.7(4) . . ? C13 C12 C11 119.6(4) . . ? C12 C13 C14 121.9(5) . . ? C15 C14 C13 119.6(4) . . ? C14 C15 C16 120.8(4) . . ? C17 C16 C11 120.4(4) . . ? C17 C16 C15 121.9(4) . . ? C11 C16 C15 117.7(4) . . ? C18 C17 C16 120.4(4) . . ? C17 C18 C9 120.7(4) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 26.30 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.667 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.114 # Attachment '- bw cpd 6.cif' data_bw3 _database_code_depnum_ccdc_archive 'CCDC 845906' #TrackingRef '- bw cpd 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 Cl4 N2, I' _chemical_formula_sum 'C19 H13 Cl4 I N2' _chemical_formula_weight 538.01 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.500(3) _cell_length_b 12.9443(12) _cell_length_c 14.1288(13) _cell_angle_alpha 90.00 _cell_angle_beta 117.003(2) _cell_angle_gamma 90.00 _cell_volume 3992.3(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6716 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.34 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 2.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6086 _exptl_absorpt_correction_T_max 0.8522 _exptl_absorpt_process_details 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 'CCD Area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17009 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4569 _reflns_number_gt 3929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+8.2992P] 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 4569 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.004 _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 I1 I 0.129848(9) 0.066152(15) 0.999118(15) 0.02739(8) Uani 1 1 d . . . Cl1 Cl 0.29555(4) 0.70008(6) 0.21179(6) 0.03126(17) Uani 1 1 d . . . Cl2 Cl 0.22190(5) 0.59993(6) -0.00836(7) 0.0432(2) Uani 1 1 d . . . Cl4 Cl 0.01370(4) 0.78486(8) -0.04996(8) 0.0507(3) Uani 1 1 d . . . Cl3 Cl 0.08198(6) 0.63824(8) -0.13781(7) 0.0585(3) Uani 1 1 d . . . N2 N 0.20807(10) 0.84849(17) 0.27101(18) 0.0194(5) Uani 1 1 d . . . N1 N 0.10973(11) 0.8789(2) 0.1790(2) 0.0265(5) Uani 1 1 d . . . C9 C 0.31353(13) 0.9171(2) 0.3404(2) 0.0209(6) Uani 1 1 d . . . C17 C 0.33648(13) 1.0492(2) 0.2431(2) 0.0194(5) Uani 1 1 d . . . C12 C 0.39958(13) 1.0376(2) 0.3102(2) 0.0227(6) Uani 1 1 d . . . C13 C 0.44186(14) 1.1006(2) 0.2936(2) 0.0262(6) Uani 1 1 d . . . H13 H 0.4837 1.0942 0.3377 0.031 Uiso 1 1 calc R . . C2 C 0.21910(14) 0.7262(2) 0.1394(2) 0.0241(6) Uani 1 1 d . . . C16 C 0.31650(13) 1.1216(2) 0.1586(2) 0.0215(6) Uani 1 1 d . . . H16 H 0.2749 1.1284 0.1131 0.026 Uiso 1 1 calc R . . C3 C 0.18509(16) 0.6803(2) 0.0416(2) 0.0295(7) Uani 1 1 d . . . C11 C 0.41897(14) 0.9608(2) 0.3913(2) 0.0265(6) Uani 1 1 d . . . H11 H 0.4606 0.9503 0.4346 0.032 Uiso 1 1 calc R . . C5 C 0.09104(15) 0.7641(3) 0.0203(2) 0.0320(7) Uani 1 1 d . . . C1 C 0.18802(13) 0.7915(2) 0.1769(2) 0.0208(6) Uani 1 1 d . . . C10 C 0.37701(14) 0.9025(2) 0.4059(2) 0.0259(6) Uani 1 1 d . . . H10 H 0.3902 0.8529 0.4593 0.031 Uiso 1 1 calc R . . C4 C 0.12189(16) 0.6986(3) -0.0173(2) 0.0344(8) Uani 1 1 d . . . C15 C 0.35778(13) 1.1813(2) 0.1435(2) 0.0229(6) Uani 1 1 d . . . H15 H 0.3442 1.2286 0.0880 0.027 Uiso 1 1 calc R . . C18 C 0.29376(13) 0.9880(2) 0.2603(2) 0.0204(5) Uani 1 1 d . . . H18 H 0.2520 0.9962 0.2167 0.024 Uiso 1 1 calc R . . C7 C 0.16006(14) 0.8991(2) 0.2678(2) 0.0231(6) Uani 1 1 d . . . H7 H 0.1616 0.9431 0.3210 0.028 Uiso 1 1 calc R . . C14 C 0.42073(14) 1.1713(2) 0.2118(2) 0.0255(6) Uani 1 1 d . . . H14 H 0.4485 1.2131 0.2017 0.031 Uiso 1 1 calc R . . C6 C 0.12563(13) 0.8109(2) 0.1188(2) 0.0242(6) Uani 1 1 d . . . C8 C 0.26907(13) 0.8526(2) 0.3625(2) 0.0226(6) Uani 1 1 d . . . H8A H 0.2850 0.7829 0.3809 0.027 Uiso 1 1 calc R . . H8B H 0.2656 0.8814 0.4229 0.027 Uiso 1 1 calc R . . C19 C 0.05022(16) 0.9275(3) 0.1540(3) 0.0385(8) Uani 1 1 d . . . H19A H 0.0536 0.9664 0.2143 0.058 Uiso 1 1 calc R . . H19B H 0.0196 0.8749 0.1373 0.058 Uiso 1 1 calc R . . H19C H 0.0388 0.9728 0.0942 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02719(12) 0.02960(13) 0.02542(12) 0.00491(7) 0.01199(9) -0.00261(8) Cl1 0.0346(4) 0.0259(4) 0.0374(4) 0.0009(3) 0.0200(3) 0.0047(3) Cl2 0.0834(7) 0.0244(4) 0.0393(5) -0.0063(3) 0.0429(5) -0.0039(4) Cl4 0.0317(4) 0.0534(6) 0.0428(5) 0.0053(4) -0.0043(4) -0.0123(4) Cl3 0.0802(8) 0.0547(6) 0.0254(4) -0.0166(4) 0.0108(5) -0.0261(5) N2 0.0230(12) 0.0188(11) 0.0169(11) -0.0004(9) 0.0094(9) -0.0047(9) N1 0.0252(13) 0.0253(13) 0.0321(14) 0.0058(10) 0.0156(11) -0.0004(10) C9 0.0234(14) 0.0200(13) 0.0194(14) -0.0023(10) 0.0098(11) -0.0033(11) C17 0.0231(14) 0.0168(13) 0.0195(13) -0.0035(10) 0.0107(11) -0.0003(10) C12 0.0265(15) 0.0201(13) 0.0242(14) -0.0047(11) 0.0138(12) -0.0014(11) C13 0.0235(14) 0.0289(15) 0.0291(16) -0.0033(12) 0.0145(13) -0.0013(12) C2 0.0354(16) 0.0169(13) 0.0243(14) 0.0022(11) 0.0172(13) -0.0024(12) C16 0.0255(14) 0.0185(13) 0.0220(14) -0.0012(11) 0.0122(12) 0.0022(11) C3 0.050(2) 0.0197(14) 0.0257(15) -0.0017(11) 0.0232(15) -0.0065(13) C11 0.0214(14) 0.0281(15) 0.0264(15) 0.0012(12) 0.0078(12) -0.0024(12) C5 0.0313(16) 0.0298(16) 0.0250(15) 0.0028(13) 0.0041(13) -0.0092(13) C1 0.0281(14) 0.0175(13) 0.0165(13) 0.0000(10) 0.0100(11) -0.0044(11) C10 0.0286(15) 0.0251(15) 0.0208(14) 0.0033(11) 0.0084(12) -0.0008(12) C4 0.051(2) 0.0270(16) 0.0197(15) -0.0052(12) 0.0113(14) -0.0148(15) C15 0.0317(15) 0.0189(13) 0.0236(14) -0.0002(11) 0.0174(12) 0.0018(11) C18 0.0208(13) 0.0209(13) 0.0180(13) -0.0037(10) 0.0077(11) -0.0010(11) C7 0.0294(15) 0.0202(13) 0.0257(15) 0.0009(11) 0.0179(13) -0.0027(12) C14 0.0295(15) 0.0226(14) 0.0324(16) -0.0038(12) 0.0209(13) -0.0044(12) C6 0.0267(15) 0.0198(14) 0.0249(14) 0.0036(11) 0.0106(12) -0.0046(11) C8 0.0252(14) 0.0232(14) 0.0182(13) -0.0006(11) 0.0089(11) -0.0050(11) C19 0.0256(17) 0.046(2) 0.045(2) 0.0115(16) 0.0175(16) 0.0057(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.711(3) . ? Cl2 C3 1.724(3) . ? Cl4 C5 1.715(3) . ? Cl3 C4 1.719(3) . ? N2 C7 1.329(4) . ? N2 C1 1.400(3) . ? N2 C8 1.467(3) . ? N1 C7 1.326(4) . ? N1 C6 1.396(4) . ? N1 C19 1.476(4) . ? C9 C18 1.363(4) . ? C9 C10 1.416(4) . ? C9 C8 1.513(4) . ? C17 C12 1.407(4) . ? C17 C16 1.418(4) . ? C17 C18 1.420(4) . ? C12 C13 1.420(4) . ? C12 C11 1.425(4) . ? C13 C14 1.377(4) . ? C2 C3 1.382(4) . ? C2 C1 1.393(4) . ? C16 C15 1.364(4) . ? C3 C4 1.406(5) . ? C11 C10 1.364(4) . ? C5 C4 1.392(5) . ? C5 C6 1.397(4) . ? C1 C6 1.391(4) . ? C15 C14 1.405(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N2 C1 107.7(2) . . ? C7 N2 C8 123.0(2) . . ? C1 N2 C8 129.3(2) . . ? C7 N1 C6 107.7(2) . . ? C7 N1 C19 122.4(3) . . ? C6 N1 C19 129.9(3) . . ? C18 C9 C10 120.2(3) . . ? C18 C9 C8 121.6(3) . . ? C10 C9 C8 118.1(3) . . ? C12 C17 C16 119.5(3) . . ? C12 C17 C18 119.6(3) . . ? C16 C17 C18 120.9(3) . . ? C17 C12 C13 119.2(3) . . ? C17 C12 C11 118.7(3) . . ? C13 C12 C11 122.1(3) . . ? C14 C13 C12 119.8(3) . . ? C3 C2 C1 117.1(3) . . ? C3 C2 Cl1 120.8(2) . . ? C1 C2 Cl1 122.1(2) . . ? C15 C16 C17 120.6(3) . . ? C2 C3 C4 121.5(3) . . ? C2 C3 Cl2 118.6(3) . . ? C4 C3 Cl2 119.9(2) . . ? C10 C11 C12 120.5(3) . . ? C4 C5 C6 117.1(3) . . ? C4 C5 Cl4 121.5(2) . . ? C6 C5 Cl4 121.3(3) . . ? C6 C1 C2 122.0(3) . . ? C6 C1 N2 106.4(2) . . ? C2 C1 N2 131.6(3) . . ? C11 C10 C9 120.5(3) . . ? C5 C4 C3 121.3(3) . . ? C5 C4 Cl3 119.5(3) . . ? C3 C4 Cl3 119.2(3) . . ? C16 C15 C14 120.1(3) . . ? C9 C18 C17 120.4(3) . . ? N1 C7 N2 111.3(3) . . ? C13 C14 C15 120.9(3) . . ? C1 C6 C5 121.1(3) . . ? C1 C6 N1 106.9(2) . . ? C5 C6 N1 132.0(3) . . ? N2 C8 C9 112.3(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.358 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.112 # Attachment '- bw cpd1.cif' data_bw4 _database_code_depnum_ccdc_archive 'CCDC 845907' #TrackingRef '- bw cpd1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H2 Cl4 N2' _chemical_formula_sum 'C7 H2 Cl4 N2' _chemical_formula_weight 255.91 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' Cl Cl 0.1484 0.1585 '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 7.4984(19) _cell_length_b 15.060(4) _cell_length_c 16.612(4) _cell_angle_alpha 108.611(4) _cell_angle_beta 94.721(4) _cell_angle_gamma 90.265(4) _cell_volume 1770.9(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6123 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 28.02 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.920 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 1.280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7974 _exptl_absorpt_correction_T_max 0.8827 _exptl_absorpt_process_details 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13921 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 26.30 _reflns_number_total 7025 _reflns_number_gt 6112 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.8804P] 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 7025 _refine_ls_number_parameters 485 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.002 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 Cl1 Cl 0.89122(10) 0.19123(5) 1.12392(5) 0.02453(18) Uani 1 1 d . . . Cl2 Cl 0.71774(10) 0.00140(5) 1.11889(5) 0.02413(18) Uani 1 1 d . . . Cl3 Cl 0.62000(10) -0.15499(5) 0.94540(5) 0.02452(18) Uani 1 1 d . . . Cl4 Cl 0.69109(11) -0.12008(5) 0.77377(5) 0.02603(18) Uani 1 1 d . . . Cl5 Cl 0.18320(10) 0.23196(5) 0.66908(5) 0.02453(18) Uani 1 1 d . . . Cl6 Cl 0.36692(11) 0.06703(6) 0.71596(5) 0.02786(19) Uani 1 1 d . . . Cl7 Cl 0.41592(10) -0.12335(5) 0.57517(5) 0.02659(18) Uani 1 1 d . . . Cl8 Cl 0.28250(10) -0.14922(5) 0.38341(5) 0.02429(18) Uani 1 1 d . . . Cl9 Cl 0.84584(10) 0.59989(5) 1.13311(5) 0.02467(18) Uani 1 1 d . . . Cl10 Cl 0.67542(11) 0.39960(6) 1.10700(5) 0.02611(18) Uani 1 1 d . . . Cl11 Cl 0.53971(10) 0.27012(5) 0.92525(5) 0.02384(18) Uani 1 1 d . . . Cl12 Cl 0.59285(10) 0.33458(5) 0.76572(5) 0.02380(18) Uani 1 1 d . . . Cl13 Cl 0.87215(10) 0.33156(5) 0.33977(5) 0.02463(18) Uani 1 1 d . . . Cl14 Cl 0.70372(11) 0.51188(5) 0.31122(5) 0.02551(18) Uani 1 1 d . . . Cl15 Cl 0.58408(10) 0.67366(5) 0.46481(5) 0.02356(18) Uani 1 1 d . . . Cl16 Cl 0.63317(10) 0.65777(5) 0.65090(5) 0.02340(18) Uani 1 1 d . . . N1 N 0.8857(3) 0.08002(17) 0.81162(17) 0.0178(5) Uani 1 1 d . . . N2 N 0.9651(3) 0.19259(17) 0.93585(15) 0.0185(5) Uani 1 1 d . . . N3 N 0.0995(3) 0.03215(17) 0.36470(15) 0.0191(5) Uani 1 1 d . . . N4 N 0.0576(3) 0.16861(18) 0.46609(16) 0.0185(5) Uani 1 1 d . . . N5 N 0.7627(3) 0.53855(17) 0.82020(16) 0.0191(5) Uani 1 1 d . . . N6 N 0.8541(3) 0.63475(18) 0.95131(16) 0.0190(5) Uani 1 1 d . . . N7 N 0.8943(3) 0.34616(17) 0.53617(16) 0.0192(5) Uani 1 1 d . . . N8 N 0.8011(3) 0.46210(17) 0.64520(16) 0.0191(5) Uani 1 1 d . . . C1 C 0.9646(4) 0.1655(2) 0.85190(19) 0.0204(6) Uani 1 1 d . . . H1 H 1.0151 0.2028 0.8224 0.025 Uiso 1 1 calc R . . C2 C 0.8810(4) 0.1180(2) 0.95171(19) 0.0175(6) Uani 1 1 d . . . C3 C 0.8421(4) 0.1046(2) 1.02804(19) 0.0194(6) Uani 1 1 d . . . C4 C 0.7618(4) 0.0197(2) 1.02516(19) 0.0200(6) Uani 1 1 d . . . C5 C 0.7170(4) -0.0509(2) 0.9468(2) 0.0198(6) Uani 1 1 d . . . C6 C 0.7495(4) -0.0367(2) 0.87083(19) 0.0194(6) Uani 1 1 d . . . C7 C 0.8324(4) 0.0478(2) 0.87434(18) 0.0170(6) Uani 1 1 d . . . C8 C 0.0338(4) 0.1168(2) 0.38283(19) 0.0201(6) Uani 1 1 d . . . H8 H -0.0253 0.1393 0.3408 0.024 Uiso 1 1 calc R . . C9 C 0.1459(4) 0.1127(2) 0.50691(19) 0.0167(6) Uani 1 1 d . . . C10 C 0.2076(4) 0.1267(2) 0.59172(18) 0.0182(6) Uani 1 1 d . . . C11 C 0.2913(4) 0.0528(2) 0.61149(19) 0.0213(6) Uani 1 1 d . . . C12 C 0.3147(4) -0.0330(2) 0.5480(2) 0.0194(6) Uani 1 1 d . . . C13 C 0.2558(4) -0.04550(19) 0.46370(18) 0.0168(6) Uani 1 1 d . . . C14 C 0.1712(4) 0.0272(2) 0.44275(18) 0.0176(6) Uani 1 1 d . . . C15 C 0.8334(4) 0.6215(2) 0.86645(19) 0.0220(6) Uani 1 1 d . . . H15 H 0.8668 0.6677 0.8423 0.026 Uiso 1 1 calc R . . C16 C 0.7893(4) 0.5535(2) 0.96166(19) 0.0175(6) Uani 1 1 d . . . C17 C 0.7739(4) 0.5254(2) 1.03300(18) 0.0189(6) Uani 1 1 d . . . C18 C 0.6976(4) 0.4363(2) 1.02024(18) 0.0177(6) Uani 1 1 d . . . C19 C 0.6391(4) 0.3773(2) 0.93806(19) 0.0186(6) Uani 1 1 d . . . C20 C 0.6580(4) 0.40552(19) 0.86756(19) 0.0179(6) Uani 1 1 d . . . C21 C 0.7328(4) 0.4946(2) 0.87920(18) 0.0177(6) Uani 1 1 d . . . C22 C 0.8736(4) 0.3767(2) 0.61812(19) 0.0205(6) Uani 1 1 d . . . H22 H 0.9067 0.3418 0.6553 0.025 Uiso 1 1 calc R . . C23 C 0.8277(4) 0.41689(19) 0.50638(18) 0.0168(6) Uani 1 1 d . . . C24 C 0.8077(4) 0.42281(19) 0.42393(18) 0.0158(6) Uani 1 1 d . . . C25 C 0.7337(4) 0.5030(2) 0.41206(18) 0.0182(6) Uani 1 1 d . . . C26 C 0.6790(4) 0.5770(2) 0.48222(19) 0.0196(6) Uani 1 1 d . . . C27 C 0.6974(4) 0.5707(2) 0.56383(18) 0.0177(6) Uani 1 1 d . . . C28 C 0.7701(4) 0.48941(19) 0.57424(18) 0.0169(6) Uani 1 1 d . . . H2 H 0.887(4) 0.057(2) 0.766(2) 0.014(9) Uiso 1 1 d . . . H3 H 0.010(6) 0.223(3) 0.485(3) 0.048(12) Uiso 1 1 d . . . H4 H 0.902(5) 0.685(3) 0.991(2) 0.034(10) Uiso 1 1 d . . . H5 H 0.786(5) 0.489(3) 0.699(3) 0.042(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0320(4) 0.0226(4) 0.0166(4) 0.0027(3) 0.0033(3) -0.0017(3) Cl2 0.0260(4) 0.0298(4) 0.0214(4) 0.0139(3) 0.0064(3) 0.0030(3) Cl3 0.0268(4) 0.0190(4) 0.0308(4) 0.0116(3) 0.0050(3) -0.0015(3) Cl4 0.0336(4) 0.0203(4) 0.0210(4) 0.0025(3) 0.0008(3) -0.0069(3) Cl5 0.0313(4) 0.0221(4) 0.0171(4) 0.0020(3) 0.0020(3) -0.0017(3) Cl6 0.0328(4) 0.0336(4) 0.0183(4) 0.0108(3) -0.0015(3) -0.0033(3) Cl7 0.0251(4) 0.0250(4) 0.0329(4) 0.0143(3) 0.0008(3) 0.0030(3) Cl8 0.0267(4) 0.0166(4) 0.0263(4) 0.0017(3) 0.0048(3) 0.0002(3) Cl9 0.0295(4) 0.0273(4) 0.0139(4) 0.0026(3) -0.0005(3) 0.0016(3) Cl10 0.0322(4) 0.0304(4) 0.0205(4) 0.0141(3) 0.0052(3) 0.0050(3) Cl11 0.0259(4) 0.0187(4) 0.0291(4) 0.0102(3) 0.0048(3) -0.0013(3) Cl12 0.0309(4) 0.0193(4) 0.0174(4) 0.0009(3) 0.0012(3) -0.0055(3) Cl13 0.0332(4) 0.0217(4) 0.0163(4) 0.0012(3) 0.0066(3) 0.0023(3) Cl14 0.0349(4) 0.0266(4) 0.0165(4) 0.0095(3) 0.0003(3) -0.0014(3) Cl15 0.0267(4) 0.0175(4) 0.0281(4) 0.0098(3) 0.0017(3) 0.0010(3) Cl16 0.0285(4) 0.0162(4) 0.0219(4) 0.0001(3) 0.0061(3) 0.0015(3) N1 0.0240(13) 0.0156(13) 0.0116(13) 0.0019(10) 0.0004(10) -0.0027(10) N2 0.0225(13) 0.0169(12) 0.0155(12) 0.0047(10) 0.0012(10) -0.0027(10) N3 0.0207(13) 0.0206(13) 0.0151(12) 0.0043(10) 0.0026(10) -0.0036(10) N4 0.0218(13) 0.0147(13) 0.0196(13) 0.0056(10) 0.0046(10) -0.0003(10) N5 0.0247(13) 0.0152(12) 0.0173(13) 0.0045(10) 0.0042(10) -0.0028(10) N6 0.0246(13) 0.0153(13) 0.0155(13) 0.0025(10) 0.0023(10) -0.0017(10) N7 0.0243(13) 0.0171(12) 0.0182(13) 0.0081(10) 0.0033(10) 0.0001(10) N8 0.0268(14) 0.0161(13) 0.0137(13) 0.0034(10) 0.0031(10) -0.0003(10) C1 0.0253(16) 0.0176(15) 0.0194(15) 0.0073(12) 0.0028(12) -0.0030(12) C2 0.0182(14) 0.0149(14) 0.0189(15) 0.0047(12) 0.0019(11) 0.0004(11) C3 0.0207(15) 0.0196(15) 0.0167(15) 0.0036(12) 0.0023(12) 0.0040(12) C4 0.0166(14) 0.0284(16) 0.0184(15) 0.0115(13) 0.0043(11) 0.0034(12) C5 0.0174(14) 0.0209(15) 0.0243(16) 0.0115(13) 0.0040(12) -0.0006(11) C6 0.0202(15) 0.0171(15) 0.0184(15) 0.0023(12) 0.0005(11) 0.0003(11) C7 0.0173(14) 0.0178(15) 0.0173(15) 0.0073(12) 0.0019(11) 0.0012(11) C8 0.0234(15) 0.0202(15) 0.0182(15) 0.0080(12) 0.0026(12) -0.0029(12) C9 0.0171(14) 0.0149(14) 0.0187(14) 0.0063(11) 0.0022(11) -0.0031(11) C10 0.0217(15) 0.0146(14) 0.0168(15) 0.0022(11) 0.0040(11) -0.0028(11) C11 0.0188(15) 0.0303(17) 0.0164(15) 0.0097(13) 0.0014(12) -0.0050(12) C12 0.0193(14) 0.0119(14) 0.0291(17) 0.0093(12) 0.0023(12) 0.0002(11) C13 0.0193(14) 0.0092(13) 0.0203(15) 0.0015(11) 0.0048(11) -0.0015(10) C14 0.0180(14) 0.0180(14) 0.0171(14) 0.0051(12) 0.0049(11) -0.0050(11) C15 0.0255(16) 0.0205(15) 0.0206(16) 0.0069(12) 0.0037(12) -0.0014(12) C16 0.0189(14) 0.0130(14) 0.0188(15) 0.0025(11) 0.0014(11) 0.0027(11) C17 0.0166(14) 0.0236(16) 0.0138(14) 0.0021(12) 0.0022(11) 0.0033(11) C18 0.0198(14) 0.0190(15) 0.0178(15) 0.0095(12) 0.0068(11) 0.0051(11) C19 0.0158(14) 0.0192(15) 0.0227(16) 0.0089(12) 0.0041(11) 0.0018(11) C20 0.0205(15) 0.0120(14) 0.0192(15) 0.0021(11) 0.0023(12) 0.0020(11) C21 0.0162(14) 0.0211(15) 0.0144(14) 0.0043(12) 0.0000(11) 0.0004(11) C22 0.0233(15) 0.0208(15) 0.0184(15) 0.0074(12) 0.0020(12) -0.0014(12) C23 0.0217(15) 0.0106(13) 0.0182(14) 0.0041(11) 0.0047(11) -0.0019(11) C24 0.0180(14) 0.0121(13) 0.0153(14) 0.0013(11) 0.0024(11) -0.0020(10) C25 0.0183(14) 0.0222(15) 0.0145(14) 0.0069(12) -0.0006(11) -0.0040(11) C26 0.0212(15) 0.0155(14) 0.0217(16) 0.0054(12) 0.0019(12) -0.0005(11) C27 0.0163(14) 0.0177(14) 0.0171(14) 0.0024(11) 0.0025(11) -0.0014(11) C28 0.0179(14) 0.0153(14) 0.0164(14) 0.0034(11) 0.0019(11) -0.0036(11) _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 Cl1 C3 1.717(3) . ? Cl2 C4 1.723(3) . ? Cl3 C5 1.717(3) . ? Cl4 C6 1.719(3) . ? Cl5 C10 1.715(3) . ? Cl6 C11 1.726(3) . ? Cl7 C12 1.725(3) . ? Cl8 C13 1.725(3) . ? Cl9 C17 1.724(3) . ? Cl10 C18 1.720(3) . ? Cl11 C19 1.717(3) . ? Cl12 C20 1.717(3) . ? Cl13 C24 1.723(3) . ? Cl14 C25 1.719(3) . ? Cl15 C26 1.719(3) . ? Cl16 C27 1.719(3) . ? N1 C1 1.354(4) . ? N1 C7 1.368(4) . ? N2 C1 1.322(4) . ? N2 C2 1.393(4) . ? N3 C8 1.320(4) . ? N3 C14 1.387(4) . ? N4 C8 1.350(4) . ? N4 C9 1.379(4) . ? N5 C15 1.321(4) . ? N5 C21 1.378(4) . ? N6 C15 1.355(4) . ? N6 C16 1.380(4) . ? N7 C22 1.313(4) . ? N7 C23 1.389(4) . ? N8 C22 1.352(4) . ? N8 C28 1.370(4) . ? C2 C7 1.398(4) . ? C2 C3 1.399(4) . ? C3 C4 1.395(4) . ? C4 C5 1.407(4) . ? C5 C6 1.386(4) . ? C6 C7 1.396(4) . ? C9 C10 1.395(4) . ? C9 C14 1.411(4) . ? C10 C11 1.395(4) . ? C11 C12 1.406(4) . ? C12 C13 1.386(4) . ? C13 C14 1.392(4) . ? C16 C17 1.393(4) . ? C16 C21 1.403(4) . ? C17 C18 1.402(4) . ? C18 C19 1.403(4) . ? C19 C20 1.385(4) . ? C20 C21 1.401(4) . ? C23 C24 1.397(4) . ? C23 C28 1.396(4) . ? C24 C25 1.394(4) . ? C25 C26 1.422(4) . ? C26 C27 1.385(4) . ? C27 C28 1.396(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C7 106.1(3) . . ? C1 N2 C2 104.0(2) . . ? C8 N3 C14 104.3(2) . . ? C8 N4 C9 106.0(2) . . ? C15 N5 C21 104.2(2) . . ? C15 N6 C16 106.0(3) . . ? C22 N7 C23 104.1(2) . . ? C22 N8 C28 105.9(2) . . ? N2 C1 N1 114.1(3) . . ? N2 C2 C7 109.3(2) . . ? N2 C2 C3 131.3(3) . . ? C7 C2 C3 119.4(3) . . ? C4 C3 C2 119.0(3) . . ? C4 C3 Cl1 120.3(2) . . ? C2 C3 Cl1 120.7(2) . . ? C3 C4 C5 120.9(3) . . ? C3 C4 Cl2 119.4(2) . . ? C5 C4 Cl2 119.7(2) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 Cl3 119.9(2) . . ? C4 C5 Cl3 119.8(2) . . ? C5 C6 C7 118.4(3) . . ? C5 C6 Cl4 121.7(2) . . ? C7 C6 Cl4 119.9(2) . . ? N1 C7 C6 131.6(3) . . ? N1 C7 C2 106.4(2) . . ? C6 C7 C2 122.0(3) . . ? N3 C8 N4 114.5(3) . . ? N4 C9 C10 133.2(3) . . ? N4 C9 C14 105.8(3) . . ? C10 C9 C14 121.0(3) . . ? C11 C10 C9 118.0(3) . . ? C11 C10 Cl5 121.0(2) . . ? C9 C10 Cl5 120.9(2) . . ? C10 C11 C12 121.2(3) . . ? C10 C11 Cl6 119.3(2) . . ? C12 C11 Cl6 119.5(2) . . ? C13 C12 C11 120.3(3) . . ? C13 C12 Cl7 119.9(2) . . ? C11 C12 Cl7 119.9(2) . . ? C12 C13 C14 119.4(3) . . ? C12 C13 Cl8 122.0(2) . . ? C14 C13 Cl8 118.6(2) . . ? N3 C14 C13 130.6(3) . . ? N3 C14 C9 109.3(3) . . ? C13 C14 C9 120.1(3) . . ? N5 C15 N6 114.2(3) . . ? N6 C16 C17 133.0(3) . . ? N6 C16 C21 105.5(3) . . ? C17 C16 C21 121.5(3) . . ? C16 C17 C18 117.9(3) . . ? C16 C17 Cl9 120.0(2) . . ? C18 C17 Cl9 122.1(2) . . ? C17 C18 C19 120.9(3) . . ? C17 C18 Cl10 119.1(2) . . ? C19 C18 Cl10 119.9(2) . . ? C20 C19 C18 120.5(3) . . ? C20 C19 Cl11 119.9(2) . . ? C18 C19 Cl11 119.6(2) . . ? C19 C20 C21 119.3(3) . . ? C19 C20 Cl12 122.1(2) . . ? C21 C20 Cl12 118.6(2) . . ? N5 C21 C20 130.1(3) . . ? N5 C21 C16 110.1(3) . . ? C20 C21 C16 119.8(3) . . ? N7 C22 N8 114.4(3) . . ? N7 C23 C24 130.7(3) . . ? N7 C23 C28 109.4(3) . . ? C24 C23 C28 119.8(3) . . ? C25 C24 C23 118.5(3) . . ? C25 C24 Cl13 121.7(2) . . ? C23 C24 Cl13 119.8(2) . . ? C24 C25 C26 120.8(3) . . ? C24 C25 Cl14 119.8(2) . . ? C26 C25 Cl14 119.4(2) . . ? C27 C26 C25 120.6(3) . . ? C27 C26 Cl15 119.9(2) . . ? C25 C26 Cl15 119.5(2) . . ? C26 C27 C28 117.7(3) . . ? C26 C27 Cl16 122.6(2) . . ? C28 C27 Cl16 119.7(2) . . ? N8 C28 C27 131.3(3) . . ? N8 C28 C23 106.2(2) . . ? C27 C28 C23 122.5(3) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.30 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.591 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.116 # Attachment '- bwSCC32.cif' data_bw5 _database_code_depnum_ccdc_archive 'CCDC 845908' #TrackingRef '- bwSCC32.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 Ag Cl4 N2 O2' _chemical_formula_sum 'C11 H9 Ag Cl4 N2 O2' _chemical_formula_weight 450.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.404(2) _cell_length_b 5.5910(16) _cell_length_c 15.250(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.844(4) _cell_angle_gamma 90.00 _cell_volume 701.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2299 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.44 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5167 _exptl_absorpt_correction_T_max 0.9574 _exptl_absorpt_process_details 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5411 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 26.28 _reflns_number_total 2767 _reflns_number_gt 2538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_number_reflns 2767 _refine_ls_number_parameters 184 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.91903(5) 0.68961(7) 0.38400(3) 0.02704(13) Uani 1 1 d . . . Cl1 Cl 0.59233(16) 1.4157(3) 0.08084(10) 0.0283(3) Uani 1 1 d . . . Cl2 Cl 0.80430(18) 1.8274(3) 0.02621(9) 0.0277(3) Uani 1 1 d . . . Cl4 Cl 1.33651(16) 1.4944(3) 0.25629(10) 0.0290(3) Uani 1 1 d . . . Cl3 Cl 1.17383(17) 1.8556(3) 0.10822(9) 0.0283(3) Uani 1 1 d . . . C5 C 0.8907(6) 1.6196(9) 0.1064(4) 0.0218(12) Uani 1 1 d . . . C1 C 0.9348(7) 0.9779(10) 0.3001(4) 0.0250(13) Uani 1 1 d . . . N2 N 0.8119(6) 1.0797(8) 0.2381(3) 0.0237(11) Uani 1 1 d . . . N1 N 1.0701(6) 1.1103(8) 0.2976(3) 0.0245(11) Uani 1 1 d . . . C4 C 1.0585(6) 1.6364(9) 0.1435(4) 0.0225(13) Uani 1 1 d . . . C2 C 1.0350(7) 1.2982(10) 0.2361(4) 0.0226(12) Uani 1 1 d . . . C8 C 1.2284(7) 1.0551(11) 0.3544(4) 0.0317(14) Uani 1 1 d . . . H8A H 1.2169 0.9210 0.3940 0.047 Uiso 1 1 calc R . . H8B H 1.2690 1.1956 0.3906 0.047 Uiso 1 1 calc R . . H8C H 1.3053 1.0118 0.3167 0.047 Uiso 1 1 calc R . . C7 C 0.8674(7) 1.2777(10) 0.1985(4) 0.0214(12) Uani 1 1 d . . . C6 C 0.7951(6) 1.4400(10) 0.1318(3) 0.0210(12) Uani 1 1 d . . . C3 C 1.1318(6) 1.4759(10) 0.2086(4) 0.0226(12) Uani 1 1 d . . . O1 O 0.8882(5) 0.3650(7) 0.4548(3) 0.0256(9) Uani 1 1 d . . . O2 O 0.6398(5) 0.4226(8) 0.3749(3) 0.0413(11) Uani 1 1 d . . . C9 C 0.6453(6) 0.9885(11) 0.2241(4) 0.0264(13) Uani 1 1 d . . . H9A H 0.6429 0.8445 0.2604 0.040 Uiso 1 1 calc R . . H9B H 0.6070 0.9493 0.1606 0.040 Uiso 1 1 calc R . . H9C H 0.5745 1.1108 0.2418 0.040 Uiso 1 1 calc R . . C10 C 0.7378(7) 0.3063(11) 0.4298(4) 0.0282(14) Uani 1 1 d . . . C11 C 0.6839(7) 0.0832(11) 0.4720(4) 0.0308(14) Uani 1 1 d . . . H11A H 0.6090 0.1275 0.5108 0.046 Uiso 1 1 calc R . . H11B H 0.7791 0.0025 0.5077 0.046 Uiso 1 1 calc R . . H11C H 0.6287 -0.0248 0.4248 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0343(2) 0.0218(2) 0.0273(2) 0.0038(2) 0.01157(16) 0.0031(2) Cl1 0.0245(7) 0.0289(8) 0.0299(8) 0.0025(6) 0.0021(6) 0.0012(6) Cl2 0.0361(7) 0.0232(8) 0.0237(7) 0.0036(6) 0.0062(6) 0.0037(6) Cl4 0.0234(7) 0.0264(8) 0.0370(8) -0.0021(6) 0.0058(6) -0.0005(6) Cl3 0.0347(8) 0.0238(7) 0.0286(8) 0.0011(6) 0.0118(6) -0.0054(6) C5 0.024(3) 0.019(3) 0.023(3) -0.004(2) 0.007(2) 0.002(2) C1 0.032(3) 0.022(3) 0.022(3) -0.005(2) 0.007(2) 0.006(3) N2 0.032(3) 0.019(2) 0.023(3) -0.002(2) 0.013(2) -0.001(2) N1 0.029(3) 0.021(3) 0.025(3) 0.002(2) 0.009(2) 0.0034(19) C4 0.028(3) 0.020(4) 0.021(3) 0.001(2) 0.009(2) -0.002(2) C2 0.032(3) 0.019(3) 0.017(3) -0.005(2) 0.006(2) 0.004(2) C8 0.035(3) 0.028(3) 0.030(3) 0.002(3) 0.002(3) -0.002(3) C7 0.024(3) 0.021(3) 0.021(3) -0.003(2) 0.009(2) -0.002(2) C6 0.021(3) 0.024(3) 0.018(3) -0.002(2) 0.006(2) 0.003(2) C3 0.020(3) 0.025(3) 0.023(3) -0.006(2) 0.006(2) 0.002(2) O1 0.030(2) 0.026(2) 0.021(2) 0.0046(17) 0.0057(16) -0.0015(18) O2 0.035(2) 0.042(3) 0.042(3) 0.006(2) -0.003(2) -0.001(2) C9 0.030(3) 0.025(3) 0.025(3) -0.004(3) 0.008(2) -0.004(3) C10 0.031(3) 0.030(3) 0.023(3) -0.007(3) 0.004(3) 0.000(3) C11 0.032(3) 0.025(3) 0.036(4) -0.007(3) 0.009(3) -0.005(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 C1 2.079(6) . ? Ag1 O1 2.155(4) . ? Cl1 C6 1.727(5) . ? Cl2 C5 1.734(6) . ? Cl4 C3 1.728(5) . ? Cl3 C4 1.716(5) . ? C5 C6 1.390(7) . ? C5 C4 1.412(7) . ? C1 N1 1.364(7) . ? C1 N2 1.372(7) . ? N2 C7 1.388(7) . ? N2 C9 1.463(7) . ? N1 C2 1.399(7) . ? N1 C8 1.464(7) . ? C4 C3 1.385(8) . ? C2 C3 1.402(8) . ? C2 C7 1.412(8) . ? C7 C6 1.404(8) . ? O1 C10 1.285(7) . ? O2 C10 1.232(7) . ? C10 C11 1.515(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ag1 O1 172.28(19) . . ? C6 C5 C4 121.5(5) . . ? C6 C5 Cl2 119.9(4) . . ? C4 C5 Cl2 118.5(4) . . ? N1 C1 N2 105.6(5) . . ? N1 C1 Ag1 126.6(4) . . ? N2 C1 Ag1 127.7(4) . . ? C1 N2 C7 111.0(5) . . ? C1 N2 C9 121.2(5) . . ? C7 N2 C9 127.7(5) . . ? C1 N1 C2 111.3(5) . . ? C1 N1 C8 122.1(5) . . ? C2 N1 C8 126.6(5) . . ? C3 C4 C5 120.3(5) . . ? C3 C4 Cl3 119.4(4) . . ? C5 C4 Cl3 120.3(4) . . ? N1 C2 C3 132.6(5) . . ? N1 C2 C7 105.5(5) . . ? C3 C2 C7 121.8(5) . . ? N2 C7 C6 134.2(5) . . ? N2 C7 C2 106.5(5) . . ? C6 C7 C2 119.3(5) . . ? C5 C6 C7 118.7(5) . . ? C5 C6 Cl1 120.3(4) . . ? C7 C6 Cl1 121.0(4) . . ? C4 C3 C2 118.3(5) . . ? C4 C3 Cl4 121.4(4) . . ? C2 C3 Cl4 120.4(4) . . ? C10 O1 Ag1 106.2(4) . . ? O2 C10 O1 123.1(6) . . ? O2 C10 C11 120.4(6) . . ? O1 C10 C11 116.5(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.029 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.118 # Attachment '- bwSCC33.cif' data_bw6 _database_code_depnum_ccdc_archive 'CCDC 845909' #TrackingRef '- bwSCC33.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 Ag Cl4 N2 O3, C1 H2 Cl2' _chemical_formula_sum 'C13 H13 Ag Cl6 N2 O3' _chemical_formula_weight 565.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' 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 8.616(3) _cell_length_b 13.028(5) _cell_length_c 17.176(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.684(5) _cell_angle_gamma 90.00 _cell_volume 1925.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3662 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.93 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.951 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 1.895 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6327 _exptl_absorpt_correction_T_max 0.9213 _exptl_absorpt_process_details 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 'CCD Area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14692 _diffrn_reflns_av_R_equivalents 0.0908 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.30 _reflns_number_total 3909 _reflns_number_gt 3167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0694P)^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 3909 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.32137(4) 0.45975(2) 0.99421(2) 0.02786(16) Uani 1 1 d . . . Cl1 Cl 0.77846(13) 0.14570(9) 1.16302(6) 0.0272(3) Uani 1 1 d . . . Cl2 Cl 0.74548(13) -0.09320(8) 0.90702(6) 0.0243(3) Uani 1 1 d . . . Cl3 Cl 0.52032(13) 0.05890(8) 0.82092(6) 0.0235(3) Uani 1 1 d . . . Cl4 Cl 0.86682(14) -0.05186(8) 1.07664(7) 0.0259(3) Uani 1 1 d . . . Cl6 Cl -0.0996(3) 0.0227(3) 0.73165(18) 0.0777(14) Uani 0.600(5) 1 d P A 1 Cl7 Cl 0.1256(6) 0.1839(4) 0.6990(3) 0.0696(14) Uani 0.600(5) 1 d P A 1 Cl8 Cl 0.1867(7) 0.1617(5) 0.6827(4) 0.0467(13) Uani 0.400(5) 1 d P A 2 Cl9 Cl -0.0828(4) 0.1538(4) 0.7766(2) 0.0686(19) Uani 0.400(5) 1 d P A 2 O1 O 0.5317(4) 0.4291(2) 0.83167(18) 0.0282(8) Uani 1 1 d . . . H1 H 0.4832 0.4454 0.8697 0.042 Uiso 1 1 calc R . . O2 O 0.1669(4) 0.5838(3) 0.9776(3) 0.0483(11) Uani 1 1 d . . . O3 O 0.1975(6) 0.6198(4) 1.1015(4) 0.0854(19) Uani 1 1 d . . . N1 N 0.4495(4) 0.2575(3) 0.9351(2) 0.0186(8) Uani 1 1 d . . . N2 N 0.5377(4) 0.2850(3) 1.0541(2) 0.0185(8) Uani 1 1 d . . . C1 C 0.4468(5) 0.3240(3) 0.9958(2) 0.0190(9) Uani 1 1 d . . . C2 C 0.3718(5) 0.2801(3) 0.8594(2) 0.0237(10) Uani 1 1 d . . . H2A H 0.2834 0.3245 0.8671 0.028 Uiso 1 1 calc R . . H2B H 0.3332 0.2167 0.8361 0.028 Uiso 1 1 calc R . . C3 C 0.4798(6) 0.3318(3) 0.8041(2) 0.0252(10) Uani 1 1 d . . . H3A H 0.5692 0.2879 0.7973 0.030 Uiso 1 1 calc R . . H3B H 0.4260 0.3402 0.7537 0.030 Uiso 1 1 calc R . . C4 C 0.5467(5) 0.1748(3) 0.9549(2) 0.0168(8) Uani 1 1 d . . . C5 C 0.6033(5) 0.1922(3) 1.0309(2) 0.0180(9) Uani 1 1 d . . . C6 C 0.7030(5) 0.1238(3) 1.0700(2) 0.0194(9) Uani 1 1 d . . . C7 C 0.7458(5) 0.0363(3) 1.0301(3) 0.0172(9) Uani 1 1 d . . . C8 C 0.6893(5) 0.0176(3) 0.9529(2) 0.0171(9) Uani 1 1 d . . . C9 C 0.5896(5) 0.0864(3) 0.9143(2) 0.0175(9) Uani 1 1 d . . . C10 C 0.5626(6) 0.3360(3) 1.1293(3) 0.0274(10) Uani 1 1 d . . . H10A H 0.5051 0.3992 1.1292 0.041 Uiso 1 1 calc R . . H10B H 0.6713 0.3503 1.1384 0.041 Uiso 1 1 calc R . . H10C H 0.5278 0.2921 1.1699 0.041 Uiso 1 1 calc R . . C11 C 0.1369(6) 0.6335(4) 1.0371(5) 0.0507(17) Uani 1 1 d . . . C12 C 0.0189(7) 0.7191(4) 1.0281(5) 0.068(2) Uani 1 1 d . . . H12A H 0.0103 0.7535 1.0771 0.102 Uiso 1 1 calc R . . H12B H -0.0802 0.6910 1.0116 0.102 Uiso 1 1 calc R . . H12C H 0.0517 0.7672 0.9898 0.102 Uiso 1 1 calc R . . C13 C 0.0520(17) 0.0577(10) 0.6749(9) 0.051(3) Uani 0.600(5) 1 d P A 1 H13A H 0.0167 0.0565 0.6204 0.061 Uiso 0.600(5) 1 calc PR A 1 H13B H 0.1354 0.0081 0.6820 0.061 Uiso 0.600(5) 1 calc PR A 1 C14 C 0.027(2) 0.0922(14) 0.7065(12) 0.049(5) Uani 0.400(5) 1 d P A 2 H14A H 0.0608 0.0257 0.7265 0.059 Uiso 0.400(5) 1 calc PR A 2 H14B H -0.0383 0.0806 0.6598 0.059 Uiso 0.400(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0299(3) 0.0156(2) 0.0385(3) 0.00372(14) 0.00636(17) 0.00628(13) Cl1 0.0337(6) 0.0254(6) 0.0217(6) -0.0037(4) -0.0075(5) 0.0022(5) Cl2 0.0288(6) 0.0156(5) 0.0288(6) -0.0053(4) 0.0039(5) 0.0033(4) Cl3 0.0318(6) 0.0203(5) 0.0181(5) -0.0029(4) -0.0011(4) -0.0010(4) Cl4 0.0265(6) 0.0212(6) 0.0296(6) 0.0028(4) -0.0017(5) 0.0071(4) Cl6 0.0346(15) 0.141(4) 0.0571(19) 0.048(2) -0.0031(13) -0.0052(17) Cl7 0.077(3) 0.048(2) 0.080(3) 0.004(2) -0.041(3) -0.003(2) Cl8 0.038(3) 0.053(3) 0.049(2) -0.001(2) 0.002(2) -0.004(2) Cl9 0.040(2) 0.120(4) 0.047(2) 0.049(3) 0.0115(17) 0.035(2) O1 0.050(2) 0.0118(15) 0.0230(18) -0.0002(13) 0.0078(15) 0.0004(14) O2 0.039(2) 0.024(2) 0.083(3) 0.012(2) 0.018(2) 0.0152(16) O3 0.056(3) 0.082(4) 0.114(4) -0.063(3) -0.036(3) 0.029(3) N1 0.0196(19) 0.0153(18) 0.0212(18) 0.0026(14) 0.0029(14) 0.0024(14) N2 0.027(2) 0.0099(16) 0.0192(18) 0.0023(14) 0.0043(15) 0.0024(14) C1 0.024(2) 0.015(2) 0.018(2) 0.0030(17) 0.0042(17) -0.0003(17) C2 0.027(2) 0.024(2) 0.019(2) -0.0002(19) -0.0079(18) 0.0020(19) C3 0.045(3) 0.015(2) 0.015(2) 0.0003(17) -0.0017(19) 0.0006(19) C4 0.017(2) 0.013(2) 0.021(2) 0.0024(17) 0.0024(16) -0.0016(16) C5 0.022(2) 0.0105(19) 0.022(2) -0.0002(16) 0.0052(17) -0.0006(16) C6 0.019(2) 0.020(2) 0.019(2) -0.0011(17) 0.0019(17) -0.0033(17) C7 0.018(2) 0.014(2) 0.019(2) 0.0048(16) -0.0005(17) 0.0007(15) C8 0.015(2) 0.0129(19) 0.024(2) -0.0013(17) 0.0076(17) 0.0004(16) C9 0.022(2) 0.018(2) 0.012(2) -0.0003(16) 0.0002(16) -0.0010(17) C10 0.045(3) 0.020(2) 0.018(2) 0.0019(18) 0.003(2) 0.002(2) C11 0.024(3) 0.021(3) 0.107(6) -0.012(3) -0.003(3) -0.004(2) C12 0.030(3) 0.025(3) 0.150(7) -0.003(4) 0.012(4) 0.008(2) C13 0.048(7) 0.044(8) 0.062(9) -0.009(6) 0.005(7) -0.011(6) C14 0.054(12) 0.035(11) 0.058(13) 0.005(9) -0.009(10) -0.008(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 C1 2.072(4) . ? Ag1 O2 2.104(4) . ? Ag1 Ag1 3.2494(13) 3_667 ? Cl1 C6 1.720(4) . ? Cl2 C8 1.725(4) . ? Cl3 C9 1.723(4) . ? Cl4 C7 1.723(4) . ? Cl6 C13 1.728(15) . ? Cl7 C13 1.803(14) . ? Cl8 C14 1.71(2) . ? Cl9 C14 1.76(2) . ? O1 C3 1.418(5) . ? O1 H1 0.8200 . ? O2 C11 1.248(8) . ? O3 C11 1.214(8) . ? N1 C1 1.357(5) . ? N1 C4 1.397(5) . ? N1 C2 1.464(5) . ? N2 C1 1.342(5) . ? N2 C5 1.401(5) . ? N2 C10 1.460(5) . ? C2 C3 1.518(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.390(6) . ? C4 C9 1.404(6) . ? C5 C6 1.389(6) . ? C6 C7 1.389(6) . ? C7 C8 1.412(6) . ? C8 C9 1.388(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.512(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ag1 O2 169.53(17) . . ? C1 Ag1 Ag1 77.45(12) . 3_667 ? O2 Ag1 Ag1 110.59(11) . 3_667 ? C3 O1 H1 109.5 . . ? C11 O2 Ag1 116.2(4) . . ? C1 N1 C4 109.7(3) . . ? C1 N1 C2 122.0(4) . . ? C4 N1 C2 128.0(4) . . ? C1 N2 C5 110.1(3) . . ? C1 N2 C10 123.0(4) . . ? C5 N2 C10 126.9(4) . . ? N2 C1 N1 107.5(4) . . ? N2 C1 Ag1 128.2(3) . . ? N1 C1 Ag1 124.2(3) . . ? N1 C2 C3 112.1(4) . . ? N1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? O1 C3 C2 112.4(4) . . ? O1 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? O1 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 N1 106.4(3) . . ? C5 C4 C9 120.7(4) . . ? N1 C4 C9 132.9(4) . . ? C6 C5 C4 122.1(4) . . ? C6 C5 N2 131.6(4) . . ? C4 C5 N2 106.3(4) . . ? C7 C6 C5 117.4(4) . . ? C7 C6 Cl1 119.8(3) . . ? C5 C6 Cl1 122.8(3) . . ? C6 C7 C8 121.2(4) . . ? C6 C7 Cl4 119.1(3) . . ? C8 C7 Cl4 119.7(3) . . ? C9 C8 C7 121.0(4) . . ? C9 C8 Cl2 120.2(3) . . ? C7 C8 Cl2 118.8(3) . . ? C8 C9 C4 117.7(4) . . ? C8 C9 Cl3 119.3(3) . . ? C4 C9 Cl3 123.0(3) . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 O2 125.0(5) . . ? O3 C11 C12 117.4(7) . . ? O2 C11 C12 117.6(7) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Cl6 C13 Cl7 112.2(8) . . ? Cl6 C13 H13A 109.2 . . ? Cl7 C13 H13A 109.2 . . ? Cl6 C13 H13B 109.2 . . ? Cl7 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? Cl8 C14 Cl9 112.7(11) . . ? Cl8 C14 H14A 109.1 . . ? Cl9 C14 H14A 109.1 . . ? Cl8 C14 H14B 109.1 . . ? Cl9 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.593 _refine_diff_density_min -0.836 _refine_diff_density_rms 0.172 # Attachment '- bwSCC34.cif' data_bw7 _database_code_depnum_ccdc_archive 'CCDC 845910' #TrackingRef '- bwSCC34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H15 Ag Cl4 N2 O2, C H4 O' _chemical_formula_sum 'C22 H19 Ag Cl4 N2 O3' _chemical_formula_weight 609.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag 0.1306 4.2820 '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 10.1480(4) _cell_length_b 11.5407(4) _cell_length_c 12.1076(5) _cell_angle_alpha 106.8060(10) _cell_angle_beta 105.3150(10) _cell_angle_gamma 111.7690(10) _cell_volume 1145.37(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6748 _cell_measurement_theta_min 4.57 _cell_measurement_theta_max 66.00 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 11.596 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2751 _exptl_absorpt_correction_T_max 0.6294 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7216 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 66.36 _reflns_number_total 3486 _reflns_number_gt 3422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^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 3486 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0667 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.323 _refine_ls_restrained_S_all 1.323 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag -0.015736(16) -0.047548(15) 0.354243(14) 0.02241(9) Uani 1 1 d . . . Cl1 Cl 0.45108(6) -0.17506(5) 0.68813(5) 0.02082(13) Uani 1 1 d . . . Cl2 Cl 0.80175(6) 0.04553(5) 0.83369(5) 0.02274(13) Uani 1 1 d . . . Cl3 Cl 0.91901(6) 0.33011(5) 0.82467(5) 0.02485(14) Uani 1 1 d . . . Cl4 Cl 0.68870(6) 0.40694(5) 0.68013(6) 0.02552(14) Uani 1 1 d . . . O1 O -0.23829(19) -0.11170(17) 0.21564(17) 0.0271(4) Uani 1 1 d . . . O2 O -0.0982(2) 0.0817(2) 0.2067(2) 0.0439(5) Uani 1 1 d . . . O3 O 0.1698(2) 0.27831(19) 0.21893(19) 0.0388(5) Uani 1 1 d . . . H3 H 0.0772 0.2233 0.2015 0.058 Uiso 1 1 calc R . . N1 N 0.3340(2) 0.13734(18) 0.52543(18) 0.0181(4) Uani 1 1 d . . . N2 N 0.2525(2) -0.06182(18) 0.53239(18) 0.0167(4) Uani 1 1 d . . . C1 C 0.2057(2) 0.0135(2) 0.4811(2) 0.0185(5) Uani 1 1 d . . . C2 C 0.4117(2) 0.0137(2) 0.6099(2) 0.0158(4) Uani 1 1 d . . . C3 C 0.5139(2) -0.0178(2) 0.6810(2) 0.0165(4) Uani 1 1 d . . . C4 C 0.6709(2) 0.0814(2) 0.7471(2) 0.0171(4) Uani 1 1 d . . . C5 C 0.7236(2) 0.2113(2) 0.7429(2) 0.0189(5) Uani 1 1 d . . . C6 C 0.6215(3) 0.2438(2) 0.6750(2) 0.0190(5) Uani 1 1 d . . . C7 C 0.4636(2) 0.1422(2) 0.6059(2) 0.0169(4) Uani 1 1 d . . . C8 C 0.1427(2) -0.2015(2) 0.5093(2) 0.0202(5) Uani 1 1 d . . . H8A H 0.0381 -0.2293 0.4494 0.030 Uiso 1 1 calc R . . H8B H 0.1398 -0.2014 0.5896 0.030 Uiso 1 1 calc R . . H8C H 0.1769 -0.2668 0.4735 0.030 Uiso 1 1 calc R . . C9 C 0.3232(3) 0.2440(2) 0.4856(2) 0.0209(5) Uani 1 1 d . . . H9A H 0.2404 0.1979 0.3984 0.025 Uiso 1 1 calc R . . H9B H 0.4232 0.2991 0.4835 0.025 Uiso 1 1 calc R . . C10 C 0.2877(2) 0.3406(2) 0.5716(2) 0.0180(5) Uani 1 1 d . . . C11 C 0.3120(2) 0.3590(2) 0.6932(2) 0.0179(4) Uani 1 1 d . . . H11 H 0.3506 0.3072 0.7265 0.021 Uiso 1 1 calc R . . C12 C 0.2806(2) 0.4548(2) 0.7712(2) 0.0178(5) Uani 1 1 d . . . C13 C 0.3075(2) 0.4765(2) 0.8982(2) 0.0227(5) Uani 1 1 d . . . H13 H 0.3458 0.4253 0.9328 0.027 Uiso 1 1 calc R . . C14 C 0.2787(3) 0.5703(2) 0.9709(2) 0.0255(5) Uani 1 1 d . . . H14 H 0.2988 0.5852 1.0564 0.031 Uiso 1 1 calc R . . C15 C 0.2191(3) 0.6461(2) 0.9205(3) 0.0281(6) Uani 1 1 d . . . H15 H 0.1998 0.7115 0.9723 0.034 Uiso 1 1 calc R . . C16 C 0.1895(3) 0.6256(2) 0.7981(2) 0.0248(5) Uani 1 1 d . . . H16 H 0.1478 0.6756 0.7646 0.030 Uiso 1 1 calc R . . C17 C 0.2203(2) 0.5303(2) 0.7199(2) 0.0186(5) Uani 1 1 d . . . C18 C 0.1927(2) 0.5060(2) 0.5924(2) 0.0205(5) Uani 1 1 d . . . H18 H 0.1497 0.5536 0.5561 0.025 Uiso 1 1 calc R . . C19 C 0.2267(3) 0.4152(2) 0.5202(2) 0.0198(5) Uani 1 1 d . . . H19 H 0.2094 0.4022 0.4354 0.024 Uiso 1 1 calc R . . C20 C -0.2229(3) -0.0249(2) 0.1686(2) 0.0238(5) Uani 1 1 d . . . C21 C -0.3666(3) -0.0542(3) 0.0649(3) 0.0330(6) Uani 1 1 d . . . H21A H -0.3433 0.0231 0.0413 0.050 Uiso 1 1 calc R . . H21B H -0.4496 -0.0658 0.0946 0.050 Uiso 1 1 calc R . . H21C H -0.4010 -0.1392 -0.0092 0.050 Uiso 1 1 calc R . . C22 C 0.1909(4) 0.2606(3) 0.1073(3) 0.0379(6) Uani 1 1 d . . . H22A H 0.1295 0.2906 0.0570 0.057 Uiso 1 1 calc R . . H22B H 0.1562 0.1627 0.0581 0.057 Uiso 1 1 calc R . . H22C H 0.3017 0.3159 0.1281 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.02222(11) 0.02828(12) 0.02018(13) 0.01134(8) 0.00714(8) 0.01604(8) Cl1 0.0221(2) 0.0179(2) 0.0251(3) 0.0127(2) 0.0090(2) 0.01024(19) Cl2 0.0204(2) 0.0272(2) 0.0220(3) 0.0122(2) 0.0069(2) 0.0129(2) Cl3 0.0183(2) 0.0232(2) 0.0254(3) 0.0089(2) 0.0089(2) 0.00419(19) Cl4 0.0315(3) 0.0175(2) 0.0324(3) 0.0141(2) 0.0179(2) 0.0108(2) O1 0.0251(8) 0.0324(8) 0.0278(10) 0.0202(7) 0.0085(7) 0.0140(7) O2 0.0326(10) 0.0405(10) 0.0449(13) 0.0254(9) 0.0079(9) 0.0049(8) O3 0.0429(10) 0.0321(9) 0.0314(11) 0.0115(8) 0.0177(9) 0.0087(8) N1 0.0256(9) 0.0201(8) 0.0177(10) 0.0113(7) 0.0112(8) 0.0160(7) N2 0.0168(8) 0.0187(8) 0.0161(9) 0.0081(7) 0.0072(7) 0.0097(7) C1 0.0221(10) 0.0219(10) 0.0164(11) 0.0083(9) 0.0109(9) 0.0132(8) C2 0.0187(10) 0.0168(9) 0.0129(11) 0.0054(8) 0.0089(8) 0.0086(8) C3 0.0215(10) 0.0160(9) 0.0171(11) 0.0083(8) 0.0110(9) 0.0111(8) C4 0.0199(10) 0.0208(10) 0.0149(11) 0.0082(8) 0.0086(9) 0.0127(8) C5 0.0182(10) 0.0194(9) 0.0170(11) 0.0055(9) 0.0100(9) 0.0071(8) C6 0.0268(11) 0.0141(9) 0.0209(12) 0.0085(8) 0.0151(9) 0.0100(8) C7 0.0230(11) 0.0197(10) 0.0142(11) 0.0089(8) 0.0105(9) 0.0132(8) C8 0.0180(10) 0.0186(9) 0.0219(12) 0.0092(9) 0.0058(9) 0.0081(8) C9 0.0315(11) 0.0251(10) 0.0203(12) 0.0166(9) 0.0152(10) 0.0191(9) C10 0.0190(10) 0.0154(9) 0.0211(12) 0.0088(8) 0.0091(9) 0.0088(8) C11 0.0196(10) 0.0184(9) 0.0188(12) 0.0099(8) 0.0083(9) 0.0105(8) C12 0.0142(9) 0.0173(9) 0.0197(12) 0.0079(8) 0.0071(8) 0.0056(7) C13 0.0174(10) 0.0252(10) 0.0207(12) 0.0087(9) 0.0059(9) 0.0080(8) C14 0.0253(11) 0.0257(11) 0.0183(12) 0.0050(9) 0.0106(9) 0.0079(9) C15 0.0277(12) 0.0190(10) 0.0333(15) 0.0052(10) 0.0171(11) 0.0089(9) C16 0.0242(11) 0.0182(9) 0.0342(15) 0.0122(9) 0.0155(10) 0.0097(8) C17 0.0174(9) 0.0129(8) 0.0235(13) 0.0081(8) 0.0092(9) 0.0049(7) C18 0.0212(10) 0.0153(9) 0.0279(13) 0.0127(9) 0.0090(9) 0.0100(8) C19 0.0241(10) 0.0185(9) 0.0180(12) 0.0110(8) 0.0091(9) 0.0090(8) C20 0.0230(11) 0.0284(11) 0.0246(13) 0.0125(10) 0.0115(10) 0.0151(10) C21 0.0313(13) 0.0459(14) 0.0313(14) 0.0225(12) 0.0135(11) 0.0231(11) C22 0.0477(15) 0.0358(13) 0.0304(15) 0.0146(11) 0.0183(12) 0.0188(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 C1 2.069(2) . ? Ag1 O1 2.1223(16) . ? Ag1 Ag1 3.2663(3) 2_556 ? Cl1 C3 1.723(2) . ? Cl2 C4 1.720(2) . ? Cl3 C5 1.718(2) . ? Cl4 C6 1.724(2) . ? O1 C20 1.270(3) . ? O2 C20 1.239(3) . ? O3 C22 1.393(4) . ? N1 C1 1.354(3) . ? N1 C7 1.385(3) . ? N1 C9 1.475(3) . ? N2 C1 1.353(3) . ? N2 C2 1.390(3) . ? N2 C8 1.470(3) . ? C2 C3 1.392(3) . ? C2 C7 1.398(3) . ? C3 C4 1.391(3) . ? C4 C5 1.414(3) . ? C5 C6 1.381(3) . ? C6 C7 1.405(3) . ? C9 C10 1.510(3) . ? C10 C11 1.364(4) . ? C10 C19 1.420(3) . ? C11 C12 1.425(3) . ? C12 C13 1.416(4) . ? C12 C17 1.423(3) . ? C13 C14 1.361(3) . ? C14 C15 1.418(4) . ? C15 C16 1.361(4) . ? C16 C17 1.418(3) . ? C17 C18 1.416(4) . ? C18 C19 1.371(3) . ? C20 C21 1.497(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ag1 O1 176.68(7) . . ? C1 Ag1 Ag1 68.45(6) . 2_556 ? O1 Ag1 Ag1 114.86(5) . 2_556 ? C20 O1 Ag1 108.08(14) . . ? C1 N1 C7 110.57(18) . . ? C1 N1 C9 120.42(19) . . ? C7 N1 C9 129.01(19) . . ? C1 N2 C2 110.44(18) . . ? C1 N2 C8 122.20(18) . . ? C2 N2 C8 127.32(19) . . ? N2 C1 N1 106.65(18) . . ? N2 C1 Ag1 127.60(16) . . ? N1 C1 Ag1 125.71(16) . . ? C3 C2 N2 132.4(2) . . ? C3 C2 C7 121.44(19) . . ? N2 C2 C7 106.11(19) . . ? C4 C3 C2 118.3(2) . . ? C4 C3 Cl1 119.82(17) . . ? C2 C3 Cl1 121.91(16) . . ? C3 C4 C5 120.3(2) . . ? C3 C4 Cl2 119.80(17) . . ? C5 C4 Cl2 119.85(16) . . ? C6 C5 C4 121.31(19) . . ? C6 C5 Cl3 119.94(17) . . ? C4 C5 Cl3 118.75(18) . . ? C5 C6 C7 118.21(19) . . ? C5 C6 Cl4 119.77(17) . . ? C7 C6 Cl4 122.00(18) . . ? N1 C7 C2 106.22(18) . . ? N1 C7 C6 133.4(2) . . ? C2 C7 C6 120.4(2) . . ? N1 C9 C10 113.5(2) . . ? C11 C10 C19 119.8(2) . . ? C11 C10 C9 123.7(2) . . ? C19 C10 C9 116.5(2) . . ? C10 C11 C12 121.1(2) . . ? C13 C12 C17 119.2(2) . . ? C13 C12 C11 121.7(2) . . ? C17 C12 C11 119.1(2) . . ? C14 C13 C12 120.3(2) . . ? C13 C14 C15 120.7(2) . . ? C16 C15 C14 120.2(2) . . ? C15 C16 C17 120.7(2) . . ? C18 C17 C16 122.9(2) . . ? C18 C17 C12 118.3(2) . . ? C16 C17 C12 118.8(2) . . ? C19 C18 C17 121.5(2) . . ? C18 C19 C10 120.2(2) . . ? O2 C20 O1 123.4(2) . . ? O2 C20 C21 120.0(2) . . ? O1 C20 C21 116.6(2) . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 66.36 _diffrn_measured_fraction_theta_full 0.865 _refine_diff_density_max 0.542 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.074