# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Jean-Marie Lehn' _publ_contact_author_email LEHN@ISIS.U-STRASBG.FR _publ_section_title ; Reversible Constitutional Switching between Macrocycles and Polymers Induced by Shape Change in a Dynamic Covalent System ; loop_ _publ_author_name 'Jean-Marie Lehn' 'Eric Buhler' 'Sebastien Ulrich' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 703869' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 F6 N6 O7 S2 Zn' _chemical_formula_weight 715.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 25.1170(4) _cell_length_b 11.8990(6) _cell_length_c 9.3020(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2780.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4035 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 29.131 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 1.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8402 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method '/p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7069 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1234 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 29.11 _reflns_number_total 7069 _reflns_number_gt 3630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+1.3278P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.363(17) _refine_ls_number_reflns 7069 _refine_ls_number_parameters 397 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1665 _refine_ls_R_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.019 _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 0.7411(3) 0.1978(5) 0.5079(6) 0.0514(16) Uani 1 1 d . . . C2 C 0.7853(3) 0.1660(5) 0.4255(7) 0.0621(18) Uani 1 1 d . . . H1 H 0.7808 0.1359 0.3317 0.074 Uiso 1 1 calc . . . C3 C 0.8349(3) 0.1788(5) 0.4820(8) 0.0642(19) Uani 1 1 d . . . H2 H 0.8651 0.1578 0.4267 0.077 Uiso 1 1 calc . . . C4 C 0.8420(3) 0.2218(5) 0.6186(8) 0.0598(17) Uani 1 1 d . . . H3 H 0.8766 0.2298 0.6591 0.072 Uiso 1 1 calc . . . C5 C 0.7959(3) 0.2535(5) 0.6954(6) 0.0481(15) Uani 1 1 d . . . C6 C 0.8018(2) 0.3015(5) 0.8389(7) 0.0486(15) Uani 1 1 d . . . H4 H 0.8352 0.3087 0.8857 0.058 Uiso 1 1 calc . . . C7 C 0.8023(2) 0.3876(6) 1.1181(6) 0.0599(17) Uani 1 1 d . . . H7A H 0.8302 0.3380 1.0805 0.090 Uiso 1 1 calc . . . H7B H 0.7935 0.3656 1.2168 0.090 Uiso 1 1 calc . . . H7C H 0.8150 0.4654 1.1173 0.090 Uiso 1 1 calc . . . C8 C 0.7039(2) 0.4006(5) 1.0765(6) 0.0446(13) Uani 1 1 d . . . C9 C 0.6924(2) 0.4379(5) 1.2171(6) 0.0521(15) Uani 1 1 d . . . H9 H 0.7201 0.4497 1.2852 0.063 Uiso 1 1 calc . . . C10 C 0.6405(3) 0.4566(5) 1.2522(8) 0.0623(17) Uani 1 1 d . . . H10 H 0.6319 0.4819 1.3462 0.075 Uiso 1 1 calc . . . C11 C 0.6006(3) 0.4398(6) 1.1555(7) 0.0601(17) Uani 1 1 d . . . H11 H 0.5645 0.4534 1.1806 0.072 Uiso 1 1 calc . . . C12 C 0.6143(2) 0.4021(5) 1.0185(6) 0.0470(15) Uani 1 1 d . . . C13 C 0.5761(2) 0.3789(5) 0.9078(8) 0.0557(16) Uani 1 1 d . . . H13 H 0.5396 0.3960 0.9235 0.067 Uiso 1 1 calc . . . C14 C 0.5477(3) 0.3252(7) 0.6839(10) 0.090(2) Uani 1 1 d . . . H14A H 0.5631 0.3340 0.5865 0.108 Uiso 1 1 calc . . . H14B H 0.5224 0.3879 0.6987 0.108 Uiso 1 1 calc . . . C15 C 0.5170(4) 0.2169(11) 0.6880(10) 0.118(4) Uani 1 1 d . . . H15A H 0.4889 0.2196 0.6136 0.141 Uiso 1 1 calc . . . H15B H 0.4993 0.2103 0.7827 0.141 Uiso 1 1 calc . . . C16 C 0.5507(4) 0.1138(8) 0.6636(12) 0.104(3) Uani 1 1 d . . . H16A H 0.5323 0.0481 0.7061 0.125 Uiso 1 1 calc . . . H16B H 0.5849 0.1233 0.7150 0.125 Uiso 1 1 calc . . . C17 C 0.5625(5) 0.0888(9) 0.5038(12) 0.119(4) Uani 1 1 d . . . H17A H 0.5283 0.0811 0.4514 0.143 Uiso 1 1 calc . . . H17B H 0.5816 0.0162 0.4966 0.143 Uiso 1 1 calc . . . C18 C 0.5962(4) 0.1814(9) 0.4316(10) 0.105(3) Uani 1 1 d . . . H18A H 0.6060 0.1573 0.3333 0.126 Uiso 1 1 calc . . . H18B H 0.5748 0.2510 0.4236 0.126 Uiso 1 1 calc . . . C19 C 0.6892(3) 0.1823(6) 0.4502(7) 0.065(2) Uani 1 1 d . . . H19 H 0.6860 0.1528 0.3557 0.077 Uiso 1 1 calc R . . C20 C 0.6225(3) 0.0278(6) 1.0418(8) 0.0613(17) Uani 1 1 d . . . C21 C 0.4610(3) 0.2771(7) 1.1998(10) 0.080(2) Uani 1 1 d . . . N1 N 0.74712(19) 0.2407(4) 0.6399(5) 0.0452(11) Uani 1 1 d . . . N2 N 0.75750(18) 0.3334(4) 0.8971(5) 0.0434(12) Uani 1 1 d . . . N3 N 0.75545(18) 0.3785(4) 1.0292(5) 0.0471(12) Uani 1 1 d . . . N4 N 0.66559(17) 0.3812(4) 0.9802(5) 0.0439(11) Uani 1 1 d . . . N5 N 0.59044(19) 0.3358(4) 0.7886(6) 0.0547(13) Uani 1 1 d . . . N6 N 0.6470(3) 0.2059(5) 0.5180(6) 0.0712(16) Uani 1 1 d . . . O1 O 0.67618(15) 0.1343(3) 0.8547(4) 0.0477(10) Uani 1 1 d . . . O2 O 0.70365(19) 0.1518(4) 1.1029(4) 0.0616(12) Uani 1 1 d . . . O1W O 0.68780(16) 0.4485(4) 0.6514(5) 0.0561(11) Uani 1 1 d D . . O3 O 0.71948(15) -0.0217(3) 0.9780(4) 0.0525(10) Uani 1 1 d . . . O4 O 0.4203(2) 0.2473(6) 0.9553(7) 0.121(2) Uani 1 1 d . . . O5 O 0.37370(16) 0.3689(4) 1.1289(6) 0.0773(14) Uani 1 1 d . . . O6 O 0.45353(18) 0.4323(4) 1.0128(7) 0.104(2) Uani 1 1 d . . . F1 F 0.58828(15) 0.1108(4) 1.0497(5) 0.0875(13) Uani 1 1 d . . . F2 F 0.62546(15) -0.0206(3) 1.1721(4) 0.0781(11) Uani 1 1 d . . . F3 F 0.60505(15) -0.0483(4) 0.9499(5) 0.0824(12) Uani 1 1 d . . . F4 F 0.50683(16) 0.2416(4) 1.1535(6) 0.0985(14) Uani 1 1 d . . . F5 F 0.43487(18) 0.1905(5) 1.2520(8) 0.131(2) Uani 1 1 d . . . F6 F 0.4689(2) 0.3523(6) 1.3063(6) 0.133(2) Uani 1 1 d . . . S1 S 0.68792(6) 0.07963(12) 0.99035(14) 0.0441(4) Uani 1 1 d . . . S2 S 0.42336(7) 0.34302(17) 1.0611(2) 0.0708(5) Uani 1 1 d . . . Zn1 Zn 0.67820(2) 0.30381(5) 0.76919(8) 0.04505(18) Uani 1 1 d . . . H2W H 0.7194(9) 0.454(5) 0.609(5) 0.051(18) Uiso 1 1 d D . . H1W H 0.677(3) 0.517(3) 0.674(9) 0.10(3) Uiso 1 1 d 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 0.085(5) 0.032(3) 0.037(3) -0.001(3) 0.021(3) 0.001(3) C2 0.092(5) 0.047(4) 0.047(4) -0.007(3) 0.015(4) 0.004(4) C3 0.088(5) 0.045(4) 0.060(4) 0.007(3) 0.042(4) 0.014(4) C4 0.068(4) 0.033(4) 0.078(5) 0.012(3) 0.020(4) 0.007(3) C5 0.056(4) 0.037(4) 0.051(4) 0.004(3) 0.019(3) 0.009(3) C6 0.048(4) 0.050(4) 0.048(3) 0.002(3) 0.002(3) 0.003(3) C7 0.049(3) 0.082(5) 0.049(4) -0.018(3) -0.008(3) 0.001(3) C8 0.060(4) 0.034(3) 0.040(3) -0.001(3) 0.001(3) 0.000(3) C9 0.064(4) 0.054(4) 0.039(3) -0.002(3) -0.003(3) 0.004(3) C10 0.076(4) 0.059(4) 0.052(4) -0.009(4) 0.028(4) 0.002(3) C11 0.058(4) 0.061(4) 0.061(4) -0.001(3) 0.015(4) 0.006(3) C12 0.052(4) 0.032(3) 0.057(4) -0.001(3) 0.012(3) -0.001(3) C13 0.052(4) 0.050(4) 0.065(4) 0.009(4) 0.017(3) 0.002(3) C14 0.086(6) 0.095(6) 0.089(5) -0.015(5) -0.007(5) -0.001(5) C15 0.077(6) 0.183(11) 0.092(6) -0.035(7) 0.007(5) -0.017(7) C16 0.094(6) 0.097(7) 0.121(8) 0.021(7) -0.021(6) -0.031(5) C17 0.147(9) 0.095(8) 0.116(8) -0.030(6) -0.031(7) 0.014(7) C18 0.103(7) 0.141(9) 0.071(5) -0.019(6) -0.011(5) 0.021(6) C19 0.097(6) 0.062(5) 0.035(3) -0.002(3) 0.007(4) 0.006(4) C20 0.066(4) 0.054(4) 0.064(4) 0.009(4) 0.013(4) 0.003(4) C21 0.053(5) 0.097(6) 0.091(6) 0.027(6) 0.014(4) -0.002(4) N1 0.059(3) 0.037(3) 0.039(3) 0.004(2) 0.012(2) 0.008(2) N2 0.054(3) 0.041(3) 0.035(3) 0.000(2) 0.006(2) 0.006(2) N3 0.050(3) 0.048(3) 0.044(3) -0.007(2) 0.001(2) 0.004(2) N4 0.046(3) 0.042(3) 0.043(3) -0.002(2) 0.002(2) 0.000(2) N5 0.051(3) 0.061(3) 0.053(3) 0.001(3) -0.004(3) -0.003(2) N6 0.084(4) 0.080(5) 0.050(3) -0.002(3) 0.011(3) 0.009(3) O1 0.062(3) 0.041(2) 0.0398(19) 0.0035(19) -0.003(2) -0.0037(19) O2 0.095(3) 0.049(3) 0.041(3) -0.005(2) -0.005(2) -0.005(3) O1W 0.059(3) 0.048(3) 0.061(3) 0.012(2) 0.018(2) 0.015(2) O3 0.054(2) 0.045(2) 0.059(2) -0.007(2) -0.002(2) 0.0109(19) O4 0.076(4) 0.187(7) 0.099(4) -0.062(4) -0.006(3) 0.009(4) O5 0.055(3) 0.062(3) 0.115(4) 0.013(3) 0.022(3) 0.018(2) O6 0.059(3) 0.081(4) 0.174(6) 0.056(4) 0.030(3) 0.013(3) F1 0.072(3) 0.082(3) 0.108(3) 0.024(3) 0.030(2) 0.031(2) F2 0.092(3) 0.068(3) 0.074(2) 0.015(2) 0.025(2) -0.004(2) F3 0.084(3) 0.071(3) 0.092(3) -0.003(2) -0.011(2) -0.023(2) F4 0.056(2) 0.119(4) 0.120(3) 0.033(3) 0.019(2) 0.033(2) F5 0.104(3) 0.106(3) 0.183(6) 0.087(4) 0.051(4) 0.027(3) F6 0.119(4) 0.181(6) 0.100(4) -0.036(4) -0.011(3) -0.002(4) S1 0.0583(9) 0.0397(8) 0.0344(7) -0.0013(6) 0.0022(6) -0.0010(7) S2 0.0419(9) 0.0761(13) 0.0943(14) 0.0227(12) 0.0132(9) 0.0123(9) Zn1 0.0519(3) 0.0424(3) 0.0408(3) 0.0015(4) 0.0028(4) 0.0022(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 C1 N1 1.338(8) . ? C1 C2 1.402(9) . ? C1 C19 1.423(10) . ? C2 C3 1.360(10) . ? C2 H1 0.9500 . ? C3 C4 1.381(10) . ? C3 H2 0.9500 . ? C4 C5 1.413(8) . ? C4 H3 0.9500 . ? C5 N1 1.338(8) . ? C5 C6 1.460(8) . ? C6 N2 1.293(7) . ? C6 H4 0.9500 . ? C7 N3 1.442(7) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N4 1.335(7) . ? C8 N3 1.392(7) . ? C8 C9 1.411(8) . ? C9 C10 1.364(8) . ? C9 H9 0.9500 . ? C10 C11 1.360(9) . ? C10 H10 0.9500 . ? C11 C12 1.394(8) . ? C11 H11 0.9500 . ? C12 N4 1.360(7) . ? C12 C13 1.434(9) . ? C13 N5 1.273(8) . ? C13 H13 0.9500 . ? C14 N5 1.456(10) . ? C14 C15 1.501(13) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.507(13) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.544(15) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.545(14) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N6 1.535(11) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N6 1.264(8) . ? C19 H19 0.9500 . ? C20 F1 1.312(7) . ? C20 F3 1.320(7) . ? C20 F2 1.344(8) . ? C20 S1 1.818(6) . ? C21 F4 1.300(9) . ? C21 F5 1.314(9) . ? C21 F6 1.350(9) . ? C21 S2 1.781(8) . ? N1 Zn1 2.238(4) . ? N2 N3 1.342(6) . ? N2 Zn1 2.346(5) . ? N4 Zn1 2.192(5) . ? N5 Zn1 2.244(5) . ? O1 S1 1.450(4) . ? O1 Zn1 2.169(4) . ? O2 S1 1.411(4) . ? O1W Zn1 2.055(4) . ? O1W H2W 0.89(3) . ? O1W H1W 0.89(3) . ? O3 S1 1.448(4) . ? O4 S2 1.507(6) . ? O5 S2 1.431(4) . ? O6 S2 1.380(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.0(6) . . ? N1 C1 C19 119.9(6) . . ? C2 C1 C19 119.0(6) . . ? C3 C2 C1 118.9(6) . . ? C3 C2 H1 120.6 . . ? C1 C2 H1 120.6 . . ? C2 C3 C4 121.1(6) . . ? C2 C3 H2 119.4 . . ? C4 C3 H2 119.4 . . ? C3 C4 C5 117.2(7) . . ? C3 C4 H3 121.4 . . ? C5 C4 H3 121.4 . . ? N1 C5 C4 121.7(6) . . ? N1 C5 C6 119.3(5) . . ? C4 C5 C6 118.9(6) . . ? N2 C6 C5 114.2(6) . . ? N2 C6 H4 122.9 . . ? C5 C6 H4 122.9 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N4 C8 N3 115.2(5) . . ? N4 C8 C9 121.9(5) . . ? N3 C8 C9 122.9(5) . . ? C10 C9 C8 118.0(6) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C11 C10 C9 121.5(6) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 118.0(6) . . ? C10 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? N4 C12 C11 122.1(6) . . ? N4 C12 C13 114.2(5) . . ? C11 C12 C13 123.6(6) . . ? N5 C13 C12 120.9(5) . . ? N5 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? N5 C14 C15 115.8(8) . . ? N5 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? N5 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 114.0(8) . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 114.2(8) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C18 112.7(8) . . ? C16 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? C16 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? N6 C18 C17 111.3(7) . . ? N6 C18 H18A 109.4 . . ? C17 C18 H18A 109.4 . . ? N6 C18 H18B 109.4 . . ? C17 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? N6 C19 C1 123.4(7) . . ? N6 C19 H19 118.3 . . ? C1 C19 H19 118.3 . . ? F1 C20 F3 109.5(6) . . ? F1 C20 F2 107.9(5) . . ? F3 C20 F2 108.0(5) . . ? F1 C20 S1 110.6(5) . . ? F3 C20 S1 111.3(4) . . ? F2 C20 S1 109.5(5) . . ? F4 C21 F5 108.0(7) . . ? F4 C21 F6 109.1(7) . . ? F5 C21 F6 108.8(8) . . ? F4 C21 S2 111.9(6) . . ? F5 C21 S2 110.4(6) . . ? F6 C21 S2 108.5(6) . . ? C5 N1 C1 120.0(5) . . ? C5 N1 Zn1 117.6(4) . . ? C1 N1 Zn1 122.3(4) . . ? C6 N2 N3 122.2(5) . . ? C6 N2 Zn1 118.3(4) . . ? N3 N2 Zn1 119.5(3) . . ? N2 N3 C8 113.6(5) . . ? N2 N3 C7 121.6(5) . . ? C8 N3 C7 124.3(5) . . ? C8 N4 C12 118.5(5) . . ? C8 N4 Zn1 124.7(4) . . ? C12 N4 Zn1 116.6(4) . . ? C13 N5 C14 114.2(6) . . ? C13 N5 Zn1 114.6(4) . . ? C14 N5 Zn1 131.0(5) . . ? C19 N6 C18 113.1(6) . . ? S1 O1 Zn1 137.0(3) . . ? Zn1 O1W H2W 114(4) . . ? Zn1 O1W H1W 127(5) . . ? H2W O1W H1W 108(6) . . ? O2 S1 O3 114.4(2) . . ? O2 S1 O1 115.4(3) . . ? O3 S1 O1 114.6(2) . . ? O2 S1 C20 105.3(3) . . ? O3 S1 C20 103.5(3) . . ? O1 S1 C20 101.4(3) . . ? O6 S2 O5 117.1(3) . . ? O6 S2 O4 113.4(4) . . ? O5 S2 O4 114.0(3) . . ? O6 S2 C21 106.5(4) . . ? O5 S2 C21 103.8(4) . . ? O4 S2 C21 99.6(4) . . ? O1W Zn1 O1 167.83(17) . . ? O1W Zn1 N4 98.18(19) . . ? O1 Zn1 N4 93.38(16) . . ? O1W Zn1 N1 84.50(17) . . ? O1 Zn1 N1 84.43(16) . . ? N4 Zn1 N1 137.24(18) . . ? O1W Zn1 N5 90.91(18) . . ? O1 Zn1 N5 96.05(16) . . ? N4 Zn1 N5 73.41(18) . . ? N1 Zn1 N5 149.3(2) . . ? O1W Zn1 N2 92.57(17) . . ? O1 Zn1 N2 88.48(15) . . ? N4 Zn1 N2 66.76(15) . . ? N1 Zn1 N2 70.49(16) . . ? N5 Zn1 N2 140.12(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.3(9) . . . . ? C19 C1 C2 C3 -178.8(6) . . . . ? C1 C2 C3 C4 0.3(10) . . . . ? C2 C3 C4 C5 -1.0(9) . . . . ? C3 C4 C5 N1 1.2(9) . . . . ? C3 C4 C5 C6 -178.7(6) . . . . ? N1 C5 C6 N2 -3.5(8) . . . . ? C4 C5 C6 N2 176.4(5) . . . . ? N4 C8 C9 C10 -1.5(9) . . . . ? N3 C8 C9 C10 -179.8(5) . . . . ? C8 C9 C10 C11 0.1(10) . . . . ? C9 C10 C11 C12 0.4(10) . . . . ? C10 C11 C12 N4 0.5(9) . . . . ? C10 C11 C12 C13 178.7(6) . . . . ? N4 C12 C13 N5 4.2(8) . . . . ? C11 C12 C13 N5 -174.2(6) . . . . ? N5 C14 C15 C16 -59.3(11) . . . . ? C14 C15 C16 C17 -81.5(11) . . . . ? C15 C16 C17 C18 64.3(11) . . . . ? C16 C17 C18 N6 52.6(11) . . . . ? N1 C1 C19 N6 -0.9(10) . . . . ? C2 C1 C19 N6 178.2(6) . . . . ? C4 C5 N1 C1 -0.6(8) . . . . ? C6 C5 N1 C1 179.4(5) . . . . ? C4 C5 N1 Zn1 -176.6(4) . . . . ? C6 C5 N1 Zn1 3.4(7) . . . . ? C2 C1 N1 C5 -0.2(8) . . . . ? C19 C1 N1 C5 178.9(5) . . . . ? C2 C1 N1 Zn1 175.6(4) . . . . ? C19 C1 N1 Zn1 -5.3(7) . . . . ? C5 C6 N2 N3 179.4(5) . . . . ? C5 C6 N2 Zn1 2.0(6) . . . . ? C6 N2 N3 C8 -176.0(5) . . . . ? Zn1 N2 N3 C8 1.4(6) . . . . ? C6 N2 N3 C7 -4.0(8) . . . . ? Zn1 N2 N3 C7 173.4(4) . . . . ? N4 C8 N3 N2 -4.6(7) . . . . ? C9 C8 N3 N2 173.8(5) . . . . ? N4 C8 N3 C7 -176.4(5) . . . . ? C9 C8 N3 C7 2.1(9) . . . . ? N3 C8 N4 C12 -179.3(5) . . . . ? C9 C8 N4 C12 2.2(8) . . . . ? N3 C8 N4 Zn1 6.3(7) . . . . ? C9 C8 N4 Zn1 -172.1(4) . . . . ? C11 C12 N4 C8 -1.7(8) . . . . ? C13 C12 N4 C8 179.8(5) . . . . ? C11 C12 N4 Zn1 173.0(5) . . . . ? C13 C12 N4 Zn1 -5.4(6) . . . . ? C12 C13 N5 C14 -175.8(6) . . . . ? C12 C13 N5 Zn1 -1.0(7) . . . . ? C15 C14 N5 C13 -90.0(9) . . . . ? C15 C14 N5 Zn1 96.3(9) . . . . ? C1 C19 N6 C18 180.0(7) . . . . ? C17 C18 N6 C19 116.0(8) . . . . ? Zn1 O1 S1 O2 2.4(5) . . . . ? Zn1 O1 S1 O3 -133.7(3) . . . . ? Zn1 O1 S1 C20 115.6(4) . . . . ? F1 C20 S1 O2 63.1(6) . . . . ? F3 C20 S1 O2 -175.0(5) . . . . ? F2 C20 S1 O2 -55.7(5) . . . . ? F1 C20 S1 O3 -176.6(5) . . . . ? F3 C20 S1 O3 -54.6(5) . . . . ? F2 C20 S1 O3 64.7(5) . . . . ? F1 C20 S1 O1 -57.6(6) . . . . ? F3 C20 S1 O1 64.3(5) . . . . ? F2 C20 S1 O1 -176.4(4) . . . . ? F4 C21 S2 O6 -59.6(8) . . . . ? F5 C21 S2 O6 -180.0(6) . . . . ? F6 C21 S2 O6 60.9(6) . . . . ? F4 C21 S2 O5 176.2(6) . . . . ? F5 C21 S2 O5 55.8(8) . . . . ? F6 C21 S2 O5 -63.3(6) . . . . ? F4 C21 S2 O4 58.4(7) . . . . ? F5 C21 S2 O4 -62.0(7) . . . . ? F6 C21 S2 O4 178.9(6) . . . . ? S1 O1 Zn1 O1W 134.5(7) . . . . ? S1 O1 Zn1 N4 -27.3(4) . . . . ? S1 O1 Zn1 N1 109.9(4) . . . . ? S1 O1 Zn1 N5 -100.9(4) . . . . ? S1 O1 Zn1 N2 39.3(4) . . . . ? C8 N4 Zn1 O1W -93.3(4) . . . . ? C12 N4 Zn1 O1W 92.2(4) . . . . ? C8 N4 Zn1 O1 82.8(4) . . . . ? C12 N4 Zn1 O1 -91.6(4) . . . . ? C8 N4 Zn1 N1 -2.6(6) . . . . ? C12 N4 Zn1 N1 -177.0(3) . . . . ? C8 N4 Zn1 N5 178.2(5) . . . . ? C12 N4 Zn1 N5 3.7(4) . . . . ? C8 N4 Zn1 N2 -4.0(4) . . . . ? C12 N4 Zn1 N2 -178.5(4) . . . . ? C5 N1 Zn1 O1W 93.1(4) . . . . ? C1 N1 Zn1 O1W -82.8(4) . . . . ? C5 N1 Zn1 O1 -92.0(4) . . . . ? C1 N1 Zn1 O1 92.1(4) . . . . ? C5 N1 Zn1 N4 -3.0(5) . . . . ? C1 N1 Zn1 N4 -178.9(4) . . . . ? C5 N1 Zn1 N5 175.5(4) . . . . ? C1 N1 Zn1 N5 -0.4(6) . . . . ? C5 N1 Zn1 N2 -1.6(4) . . . . ? C1 N1 Zn1 N2 -177.5(4) . . . . ? C13 N5 Zn1 O1W -99.7(5) . . . . ? C14 N5 Zn1 O1W 74.0(6) . . . . ? C13 N5 Zn1 O1 90.3(4) . . . . ? C14 N5 Zn1 O1 -96.0(6) . . . . ? C13 N5 Zn1 N4 -1.4(4) . . . . ? C14 N5 Zn1 N4 172.3(6) . . . . ? C13 N5 Zn1 N1 179.6(4) . . . . ? C14 N5 Zn1 N1 -6.7(8) . . . . ? C13 N5 Zn1 N2 -4.6(6) . . . . ? C14 N5 Zn1 N2 169.1(5) . . . . ? C6 N2 Zn1 O1W -83.5(4) . . . . ? N3 N2 Zn1 O1W 98.9(4) . . . . ? C6 N2 Zn1 O1 84.3(4) . . . . ? N3 N2 Zn1 O1 -93.2(4) . . . . ? C6 N2 Zn1 N4 178.7(5) . . . . ? N3 N2 Zn1 N4 1.1(3) . . . . ? C6 N2 Zn1 N1 -0.3(4) . . . . ? N3 N2 Zn1 N1 -177.8(4) . . . . ? C6 N2 Zn1 N5 -178.0(4) . . . . ? N3 N2 Zn1 N5 4.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.454 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.071 data_c2 _database_code_depnum_ccdc_archive 'CCDC 703870' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H36 N13.50' _chemical_formula_weight 669.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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 0.0030 0.0019 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.46(2) _cell_length_b 4.493(4) _cell_length_c 17.260(13) _cell_angle_alpha 90.00 _cell_angle_beta 111.24(4) _cell_angle_gamma 90.00 _cell_volume 1912(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6574 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 9.52 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 705 _exptl_absorpt_coefficient_mu 0.048 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.26470 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Bruker _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3793 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 9.52 _reflns_number_total 3793 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The geometrical restrains were used for the refinement of the disordered acetonitrile molecules. ; _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^)+(0.1479P)^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 -10(10) _refine_ls_number_reflns 3793 _refine_ls_number_parameters 420 _refine_ls_number_restraints 52 _refine_ls_R_factor_all 0.1386 _refine_ls_R_factor_gt 0.0898 _refine_ls_wR_factor_ref 0.2592 _refine_ls_wR_factor_gt 0.2179 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.967 _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 C1A C 0.2710(3) -0.226(3) 0.0946(8) 0.063(3) Uani 0.50 1 d P A 1 H1A H 0.2383 -0.3256 0.0694 0.076 Uiso 0.50 1 calc PR A 1 C2A C 0.2728(5) -0.038(2) 0.1467(10) 0.073(4) Uani 0.50 1 d P A 1 H2A H 0.2415 0.0253 0.1544 0.088 Uiso 0.50 1 calc PR A 1 C3A C 0.3271(4) 0.086(2) 0.1975(6) 0.059(2) Uani 0.50 1 d P A 1 C4A C 0.3701(3) -0.0032(19) 0.1793(5) 0.0497(19) Uani 0.50 1 d P A 1 H4A H 0.4045 0.0650 0.2114 0.060 Uiso 0.50 1 calc PR A 1 C5A C 0.3641(4) -0.189(3) 0.1159(7) 0.061(3) Uani 0.50 1 d P A 1 N2A N 0.4081(3) -0.3075(15) 0.0908(6) 0.064(2) Uani 0.50 1 d P A 1 C8A C 0.64645(15) -0.134(3) 0.1896(3) 0.1010(15) Uani 0.50 1 d P B 1 H8A H 0.6736 -0.1599 0.1680 0.121 Uiso 0.50 1 calc PR B 1 C9A C 0.6583(4) 0.012(2) 0.2561(6) 0.060(2) Uani 0.50 1 d P B 1 H9A H 0.6942 0.0477 0.2894 0.072 Uiso 0.50 1 calc PR B 1 C10A C 0.6167(3) 0.1188(17) 0.2785(5) 0.0481(18) Uani 0.50 1 d P . 1 C11A C 0.5631(4) 0.022(2) 0.2349(5) 0.066(2) Uani 0.50 1 d P C 1 H11A H 0.5355 0.0593 0.2550 0.079 Uiso 0.50 1 calc PR C 1 C14A C 0.3059(4) 0.5639(15) 0.3653(5) 0.055(2) Uani 0.50 1 d P A 1 H14C H 0.2769 0.7088 0.3542 0.066 Uiso 0.50 1 calc PR A 1 H14D H 0.3395 0.6704 0.3747 0.066 Uiso 0.50 1 calc PR A 1 C15A C 0.3240(4) 0.582(2) 0.5240(7) 0.075(3) Uani 0.50 1 d P A 1 H15C H 0.3581 0.6858 0.5352 0.090 Uiso 0.50 1 calc PR A 1 H15D H 0.2955 0.7283 0.5159 0.090 Uiso 0.50 1 calc PR A 1 C16A C 0.31071(15) 0.3773(15) 0.4451(2) 0.0730(9) Uani 0.50 1 d P A 1 H16C H 0.2769 0.2732 0.4356 0.088 Uiso 0.50 1 calc PR A 1 H16D H 0.3391 0.2295 0.4551 0.088 Uiso 0.50 1 calc PR A 1 C21A C 0.4002(4) -0.568(6) 0.0178(5) 0.120(6) Uani 0.50 1 d P A 1 H21A H 0.4346 -0.6070 0.0127 0.180 Uiso 0.50 1 calc PR A 1 H21B H 0.3750 -0.4976 -0.0345 0.180 Uiso 0.50 1 calc PR A 1 H21C H 0.3866 -0.7471 0.0332 0.180 Uiso 0.50 1 calc PR A 1 N1A N 0.3148(4) -0.3041(17) 0.0696(5) 0.072(2) Uani 0.50 1 d P A 1 C6A C 0.4995(4) -0.2824(19) 0.1192(6) 0.060(2) Uani 0.50 1 d P A 1 H6A H 0.4969 -0.4285 0.0797 0.072 Uiso 0.50 1 calc PR A 1 N3A N 0.4577(3) -0.200(2) 0.1382(6) 0.061(2) Uani 0.50 1 d P A 1 N4A N 0.5940(3) -0.2637(18) 0.1441(5) 0.0636(19) Uani 0.50 1 d P B 1 C1B C 0.2714(4) -0.015(3) 0.0841(6) 0.075(3) Uani 0.50 1 d P . 2 H1B H 0.2373 0.0522 0.0500 0.090 Uiso 0.50 1 calc PR . 2 C2B C 0.2746(3) -0.224(3) 0.1558(5) 0.060(3) Uani 0.50 1 d P . 2 H2B H 0.2442 -0.2668 0.1687 0.072 Uiso 0.50 1 calc PR . 2 C3B C 0.3234(4) -0.344(2) 0.1996(5) 0.060(2) Uani 0.50 1 d P . 2 C4B C 0.3710(5) -0.259(3) 0.1804(7) 0.079(3) Uani 0.50 1 d P . 2 H4B H 0.4051 -0.3390 0.2090 0.095 Uiso 0.50 1 calc PR . 2 C5B C 0.3620(5) -0.040(3) 0.1135(8) 0.059(3) Uani 0.50 1 d P . 2 N2B N 0.4056(4) 0.047(2) 0.0907(5) 0.079(3) Uani 0.50 1 d P . 2 C8B C 0.64645(15) -0.134(3) 0.1896(3) 0.1010(15) Uani 0.50 1 d P C 2 H8B H 0.6720 -0.1446 0.1643 0.121 Uiso 0.50 1 calc PR C 2 C9B C 0.6595(4) -0.260(3) 0.2575(7) 0.079(3) Uani 0.50 1 d P C 2 H9B H 0.6958 -0.2834 0.2911 0.095 Uiso 0.50 1 calc PR C 2 C10B C 0.6161(4) -0.372(2) 0.2838(7) 0.077(3) Uani 0.50 1 d P . 2 C11B C 0.5626(3) -0.2729(18) 0.2322(6) 0.0521(19) Uani 0.50 1 d P C 2 H11B H 0.5333 -0.3243 0.2474 0.063 Uiso 0.50 1 calc PR C 2 C14B C 0.3077(5) 0.165(3) 0.3686(6) 0.086(3) Uani 0.50 1 d P A 2 H14A H 0.3420 0.0645 0.3792 0.104 Uiso 0.50 1 calc PR A 2 H14B H 0.2794 0.0163 0.3589 0.104 Uiso 0.50 1 calc PR A 2 C15B C 0.3270(4) 0.172(3) 0.5261(6) 0.074(3) Uani 0.50 1 d P A 2 H15A H 0.3007 0.0135 0.5185 0.089 Uiso 0.50 1 calc PR A 2 H15B H 0.3625 0.0838 0.5378 0.089 Uiso 0.50 1 calc PR A 2 C16B C 0.31071(15) 0.3773(15) 0.4451(2) 0.0730(9) Uani 0.50 1 d P A 2 H16A H 0.3376 0.5318 0.4524 0.088 Uiso 0.50 1 calc PR A 2 H16B H 0.2759 0.4710 0.4349 0.088 Uiso 0.50 1 calc PR A 2 C21B C 0.3950(8) 0.228(3) 0.0147(12) 0.150(8) Uani 0.50 1 d P . 2 H21D H 0.4287 0.2692 0.0076 0.225 Uiso 0.50 1 calc PR . 2 H21E H 0.3780 0.4115 0.0198 0.225 Uiso 0.50 1 calc PR . 2 H21F H 0.3715 0.1198 -0.0327 0.225 Uiso 0.50 1 calc PR . 2 N1B N 0.3131(3) 0.0739(18) 0.0676(4) 0.0590(18) Uani 0.50 1 d P . 2 C6B C 0.5007(3) 0.038(2) 0.1155(5) 0.057(2) Uani 0.50 1 d P . 2 H6B H 0.4983 0.1774 0.0745 0.069 Uiso 0.50 1 calc PR . 2 N3B N 0.4575(4) -0.046(2) 0.1351(5) 0.059(2) Uani 0.50 1 d P . 2 N4B N 0.5950(3) 0.0378(18) 0.1407(6) 0.069(2) Uani 0.50 1 d P C 2 C7 C 0.55376(14) -0.1188(18) 0.1672(2) 0.0782(11) Uani 1 1 d . . . C12 C 0.33200(17) 0.347(2) 0.2686(3) 0.109(2) Uani 1 1 d . . . H12 H 0.3621 0.4711 0.2875 0.131 Uiso 1 1 calc R A 1 C13 C 0.37376(17) 0.3489(16) 0.6470(2) 0.0820(12) Uani 1 1 d . . . H13 H 0.4022 0.4614 0.6430 0.098 Uiso 1 1 calc R . . N5 N 0.29491(11) 0.3715(13) 0.29599(16) 0.0688(8) Uani 1 1 d . A . N6 N 0.32764(12) 0.3728(14) 0.59523(17) 0.0732(8) Uani 1 1 d . . . N1S N 0.4854(5) -0.234(4) 0.3783(8) 0.163(6) Uani 0.50 1 d PDU . . C1S C 0.4591(9) -0.115(8) 0.4089(13) 0.163(6) Uani 0.25 1 d PDU D 1 C2S C 0.4357(12) 0.053(8) 0.4649(15) 0.168(11) Uani 0.25 1 d PDU D 1 C3S C 0.5171(9) -0.082(6) 0.4239(13) 0.159(6) Uani 0.25 1 d PDU D 2 C4S C 0.5513(11) 0.112(6) 0.4965(11) 0.157(9) Uani 0.25 1 d PDU D 2 C8S C 0.4389(5) -0.27(3) 0.478(5) 0.34(3) Uani 0.25 1 d PDU . 4 C7S C 0.5000 -0.288(16) 0.5000 0.35(3) Uani 0.50 2 d SPDU . 4 N3S N 0.5463(3) -0.30(2) 0.527(4) 0.35(3) Uani 0.25 1 d PDU . 4 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 C1A 0.017(3) 0.064(6) 0.102(10) 0.007(6) 0.013(4) -0.013(4) C2A 0.061(6) 0.034(4) 0.131(12) 0.017(6) 0.042(7) 0.005(4) C3A 0.048(4) 0.069(5) 0.050(5) 0.015(4) 0.003(4) -0.018(4) C4A 0.034(4) 0.055(5) 0.047(5) 0.001(4) -0.002(3) -0.008(3) C5A 0.043(4) 0.081(7) 0.042(5) 0.014(6) -0.003(3) 0.038(6) N2A 0.054(4) 0.044(4) 0.092(6) -0.004(4) 0.022(4) -0.012(3) C8A 0.054(2) 0.185(5) 0.074(3) -0.012(5) 0.0359(19) -0.020(4) C9A 0.046(5) 0.050(5) 0.072(6) 0.015(5) 0.006(4) -0.002(4) C10A 0.055(5) 0.051(4) 0.044(4) 0.008(3) 0.025(4) -0.002(3) C11A 0.056(5) 0.092(7) 0.037(4) 0.010(4) 0.002(4) 0.001(4) C14A 0.070(6) 0.025(3) 0.063(5) -0.003(3) 0.016(4) 0.001(3) C15A 0.070(6) 0.047(4) 0.094(7) 0.011(4) 0.012(5) 0.007(4) C16A 0.082(2) 0.0629(18) 0.072(2) -0.013(3) 0.0249(17) -0.006(3) C21A 0.057(5) 0.25(2) 0.045(4) -0.017(9) 0.013(3) 0.005(9) N1A 0.078(6) 0.058(4) 0.061(5) 0.009(4) 0.002(4) -0.019(4) C6A 0.061(5) 0.044(4) 0.082(6) 0.007(4) 0.035(5) 0.012(4) N3A 0.042(4) 0.066(5) 0.079(6) 0.005(5) 0.026(4) -0.023(5) N4A 0.071(5) 0.069(4) 0.055(4) -0.007(3) 0.028(4) 0.010(4) C1B 0.076(7) 0.108(9) 0.036(4) -0.006(5) 0.013(4) -0.023(6) C2B 0.050(5) 0.102(8) 0.017(3) -0.004(4) -0.001(3) 0.016(5) C3B 0.081(6) 0.063(5) 0.038(4) -0.008(4) 0.024(4) -0.020(4) C4B 0.102(8) 0.085(8) 0.053(6) -0.016(5) 0.030(5) 0.012(6) C5B 0.065(6) 0.055(5) 0.064(7) -0.001(6) 0.033(5) 0.031(5) N2B 0.057(5) 0.134(7) 0.043(4) 0.007(4) 0.014(3) 0.000(4) C8B 0.054(2) 0.185(5) 0.074(3) -0.012(5) 0.0359(19) -0.020(4) C9B 0.056(6) 0.121(11) 0.065(6) -0.024(6) 0.028(5) -0.017(6) C10B 0.050(5) 0.091(7) 0.083(7) -0.017(6) 0.016(5) -0.018(5) C11B 0.043(4) 0.046(4) 0.077(6) 0.000(4) 0.035(4) -0.009(3) C14B 0.087(8) 0.109(8) 0.055(5) -0.001(5) 0.015(5) -0.003(6) C15B 0.069(6) 0.097(7) 0.060(5) 0.027(5) 0.028(5) 0.019(5) C16B 0.082(2) 0.0629(18) 0.072(2) -0.013(3) 0.0249(17) -0.006(3) C21B 0.25(2) 0.043(5) 0.208(18) 0.008(8) 0.137(16) 0.003(8) N1B 0.040(4) 0.084(5) 0.055(4) -0.005(4) 0.021(3) -0.013(3) C6B 0.046(4) 0.097(6) 0.027(3) 0.021(4) 0.012(3) 0.002(4) N3B 0.083(6) 0.053(4) 0.035(3) -0.001(4) 0.013(3) -0.030(5) N4B 0.056(5) 0.071(5) 0.086(6) -0.005(4) 0.033(4) 0.002(4) C7 0.0569(19) 0.118(3) 0.0593(19) 0.005(4) 0.0209(15) -0.022(3) C12 0.060(2) 0.190(6) 0.071(2) 0.038(5) 0.0164(19) 0.004(4) C13 0.068(2) 0.099(3) 0.069(2) -0.013(3) 0.0123(18) 0.011(3) N5 0.0636(17) 0.0701(16) 0.0679(16) 0.007(3) 0.0182(13) 0.007(2) N6 0.0702(19) 0.0795(18) 0.0681(17) 0.006(3) 0.0229(15) 0.005(3) N1S 0.076(7) 0.279(15) 0.122(8) 0.093(10) 0.023(5) 0.020(8) C1S 0.073(9) 0.271(16) 0.130(10) 0.095(12) 0.019(7) 0.019(10) C2S 0.071(14) 0.25(2) 0.141(18) 0.086(17) -0.011(13) 0.033(16) C3S 0.075(9) 0.271(16) 0.133(10) 0.099(11) 0.039(7) 0.010(10) C4S 0.099(15) 0.25(2) 0.147(16) 0.124(15) 0.073(13) -0.014(14) C8S 0.031(10) 0.57(7) 0.40(3) 0.001(10) 0.055(18) 0.000(10) C7S 0.052(9) 0.57(7) 0.40(3) 0.000 0.054(16) 0.000 N3S 0.054(11) 0.57(7) 0.40(3) 0.000(10) 0.048(18) 0.006(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 C1A C2A 1.220(17) . ? C1A N1A 1.418(14) . ? C1A H1A 0.9300 . ? C2A C3A 1.494(14) . ? C2A H2A 0.9300 . ? C3A C4A 1.345(13) . ? C3A C12 1.666(13) . ? C4A C5A 1.340(17) . ? C4A H4A 0.9300 . ? C5A N1A 1.362(14) . ? C5A N2A 1.480(15) . ? N2A N3A 1.360(11) . ? N2A C21A 1.68(2) . ? C8A C9A 1.259(12) . ? C8A N4A 1.447(10) . ? C8A H8A 0.9300 . ? C9A C10A 1.377(13) . ? C9A H9A 0.9300 . ? C10A C11A 1.412(12) . ? C10A C13 1.597(10) 2_656 ? C11A C7 1.272(11) . ? C11A H11A 0.9300 . ? C14A N5 1.418(8) . ? C14A C16A 1.577(9) . ? C14A H14C 0.9700 . ? C14A H14D 0.9700 . ? C15A N6 1.524(11) . ? C15A C16A 1.574(12) . ? C15A H15C 0.9700 . ? C15A H15D 0.9700 . ? C16A H16C 0.9700 . ? C16A H16D 0.9700 . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 0.9600 . ? C6A N3A 1.315(13) . ? C6A C7 1.557(11) . ? C6A H6A 0.9300 . ? N4A C7 1.422(9) . ? C1B N1B 1.299(13) . ? C1B C2B 1.532(15) . ? C1B H1B 0.9300 . ? C2B C3B 1.350(13) . ? C2B H2B 0.9300 . ? C3B C4B 1.463(15) . ? C3B C12 1.791(11) 1_545 ? C4B C5B 1.470(18) . ? C4B H4B 0.9300 . ? C5B N1B 1.347(14) . ? C5B N2B 1.403(15) . ? N2B N3B 1.373(13) . ? N2B C21B 1.481(18) . ? C9B C10B 1.468(15) . ? C9B H9B 0.9300 . ? C10B C11B 1.442(13) . ? C10B C13 1.685(13) 2_646 ? C11B C7 1.267(10) . ? C11B H11B 0.9300 . ? C14B N5 1.497(12) . ? C14B H14A 0.9700 . ? C14B H14B 0.9700 . ? C15B N6 1.492(12) . ? C15B H15A 0.9700 . ? C15B H15B 0.9700 . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? C6B N3B 1.356(12) . ? C6B C7 1.534(10) . ? C6B H6B 0.9300 . ? N4B C7 1.502(9) . ? C12 N5 1.239(5) . ? C12 C3B 1.791(11) 1_565 ? C12 H12 0.9300 . ? C13 N6 1.228(4) . ? C13 C10A 1.597(10) 2_656 ? C13 C10B 1.685(13) 2_666 ? C13 H13 0.9300 . ? N1S C1S 1.145(5) . ? N1S C3S 1.146(5) . ? C1S C2S 1.525(5) . ? C3S C4S 1.525(5) . ? C8S N3S 0.45(7) 2_656 ? C8S C7S 1.522(5) . ? C7S N3S 1.144(5) 2_656 ? C7S N3S 1.144(5) . ? C7S C8S 1.522(5) 2_656 ? N3S C8S 0.45(7) 2_656 ? 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 C2A C1A N1A 125.1(9) . . ? C2A C1A H1A 117.4 . . ? N1A C1A H1A 117.4 . . ? C1A C2A C3A 117.7(10) . . ? C1A C2A H2A 121.1 . . ? C3A C2A H2A 121.1 . . ? C4A C3A C2A 117.7(10) . . ? C4A C3A C12 122.4(6) . . ? C2A C3A C12 119.8(9) . . ? C5A C4A C3A 121.2(8) . . ? C5A C4A H4A 119.4 . . ? C3A C4A H4A 119.4 . . ? C4A C5A N1A 121.4(10) . . ? C4A C5A N2A 126.2(9) . . ? N1A C5A N2A 112.3(11) . . ? N3A N2A C5A 112.7(9) . . ? N3A N2A C21A 122.0(8) . . ? C5A N2A C21A 125.1(8) . . ? C9A C8A N4A 125.3(6) . . ? C9A C8A H8A 117.4 . . ? N4A C8A H8A 117.4 . . ? C8A C9A C10A 118.5(8) . . ? C8A C9A H9A 120.8 . . ? C10A C9A H9A 120.8 . . ? C9A C10A C11A 119.6(9) . . ? C9A C10A C13 122.7(7) . 2_656 ? C11A C10A C13 117.7(7) . 2_656 ? C7 C11A C10A 117.8(9) . . ? C7 C11A H11A 121.1 . . ? C10A C11A H11A 121.1 . . ? N5 C14A C16A 109.9(5) . . ? N5 C14A H14C 109.7 . . ? C16A C14A H14C 109.7 . . ? N5 C14A H14D 109.7 . . ? C16A C14A H14D 109.7 . . ? H14C C14A H14D 108.2 . . ? N6 C15A C16A 105.4(6) . . ? N6 C15A H15C 110.7 . . ? C16A C15A H15C 110.7 . . ? N6 C15A H15D 110.7 . . ? C16A C15A H15D 110.7 . . ? H15C C15A H15D 108.8 . . ? C15A C16A C14A 111.5(6) . . ? C15A C16A H16C 109.3 . . ? C14A C16A H16C 109.3 . . ? C15A C16A H16D 109.3 . . ? C14A C16A H16D 109.3 . . ? H16C C16A H16D 108.0 . . ? N2A C21A H21A 109.5 . . ? N2A C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? N2A C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? C5A N1A C1A 116.2(10) . . ? N3A C6A C7 115.5(8) . . ? N3A C6A H6A 122.3 . . ? C7 C6A H6A 122.3 . . ? C6A N3A N2A 117.8(10) . . ? C7 N4A C8A 109.3(6) . . ? N1B C1B C2B 124.2(10) . . ? N1B C1B H1B 117.9 . . ? C2B C1B H1B 117.9 . . ? C3B C2B C1B 117.3(9) . . ? C3B C2B H2B 121.3 . . ? C1B C2B H2B 121.3 . . ? C2B C3B C4B 119.7(9) . . ? C2B C3B C12 123.2(8) . 1_545 ? C4B C3B C12 116.2(8) . 1_545 ? C3B C4B C5B 116.4(10) . . ? C3B C4B H4B 121.8 . . ? C5B C4B H4B 121.8 . . ? N1B C5B N2B 116.2(11) . . ? N1B C5B C4B 124.3(10) . . ? N2B C5B C4B 119.4(10) . . ? N3B N2B C5B 121.2(9) . . ? N3B N2B C21B 119.4(11) . . ? C5B N2B C21B 119.4(11) . . ? C10B C9B H9B 121.0 . . ? C11B C10B C9B 114.0(10) . . ? C11B C10B C13 122.4(8) . 2_646 ? C9B C10B C13 122.1(9) . 2_646 ? C7 C11B C10B 122.6(7) . . ? C7 C11B H11B 118.7 . . ? C10B C11B H11B 118.7 . . ? N5 C14B H14A 110.9 . . ? N5 C14B H14B 110.9 . . ? H14A C14B H14B 108.9 . . ? N6 C15B H15A 110.6 . . ? N6 C15B H15B 110.6 . . ? H15A C15B H15B 108.7 . . ? N2B C21B H21D 109.5 . . ? N2B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? N2B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? C1B N1B C5B 117.7(10) . . ? N3B C6B C7 113.8(7) . . ? N3B C6B H6B 123.1 . . ? C7 C6B H6B 123.1 . . ? C6B N3B N2B 122.6(8) . . ? C11B C7 C11A 62.9(4) . . ? C11B C7 N4A 94.7(6) . . ? C11A C7 N4A 124.7(6) . . ? C11B C7 N4B 127.2(6) . . ? C11A C7 N4B 97.3(7) . . ? N4A C7 N4B 55.2(3) . . ? C11B C7 C6B 127.0(5) . . ? C11A C7 C6B 97.9(7) . . ? N4A C7 C6B 131.9(5) . . ? N4B C7 C6B 102.8(6) . . ? C11B C7 C6A 92.9(6) . . ? C11A C7 C6A 123.9(6) . . ? N4A C7 C6A 105.9(6) . . ? N4B C7 C6A 133.7(5) . . ? C6B C7 C6A 55.6(3) . . ? N5 C12 C3A 118.9(7) . . ? N5 C12 C3B 104.9(7) . 1_565 ? C3A C12 C3B 95.6(3) . 1_565 ? N5 C12 H12 120.5 . . ? C3A C12 H12 120.5 . . ? C3B C12 H12 69.6 1_565 . ? N6 C13 C10A 117.9(6) . 2_656 ? N6 C13 C10B 108.2(5) . 2_666 ? C10A C13 C10B 88.5(4) 2_656 2_666 ? N6 C13 H13 121.0 . . ? C10A C13 H13 121.0 2_656 . ? C10B C13 H13 73.9 2_666 . ? C12 N5 C14A 115.4(6) . . ? C12 N5 C14B 107.1(7) . . ? C14A N5 C14B 75.9(4) . . ? C13 N6 C15B 104.4(5) . . ? C13 N6 C15A 113.4(6) . . ? C15B N6 C15A 75.5(4) . . ? C1S N1S C3S 80(2) . . ? N1S C1S C2S 168(2) . . ? N1S C3S C4S 167(2) . . ? N3S C8S C7S 28(10) 2_656 . ? N3S C7S N3S 174(10) 2_656 . ? N3S C7S C8S 10(6) 2_656 . ? N3S C7S C8S 171(5) . . ? N3S C7S C8S 171(5) 2_656 2_656 ? N3S C7S C8S 10(6) . 2_656 ? C8S C7S C8S 174(10) . 2_656 ? C8S N3S C7S 142(10) 2_656 . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 9.52 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.353 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.040 data_su28 _database_code_depnum_ccdc_archive 'CCDC 703871' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 N4 O2 Si' _chemical_formula_weight 372.54 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4521(2) _cell_length_b 28.5690(13) _cell_length_c 11.0892(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.813(2) _cell_angle_gamma 90.00 _cell_volume 2041.61(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3369 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method 'phi&omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8265 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4669 _reflns_number_gt 2580 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^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 4669 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1225 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 1.5469(3) 0.06400(9) 0.05409(18) 0.0411(6) Uani 1 1 d . . . H1A H 1.4214 0.0441 0.0560 0.049 Uiso 1 1 calc R . . H1B H 1.5052 0.0967 0.0696 0.049 Uiso 1 1 calc R . . C2 C 1.7005(3) 0.04856(8) 0.15106(18) 0.0295(5) Uani 1 1 d . . . C3 C 1.8980(3) 0.03306(8) 0.12580(19) 0.0317(5) Uani 1 1 d . . . H3 H 1.9426 0.0333 0.0454 0.038 Uiso 1 1 calc R . . C4 C 2.0276(3) 0.01727(8) 0.21941(18) 0.0315(5) Uani 1 1 d . . . H4 H 2.1598 0.0056 0.2002 0.038 Uiso 1 1 calc R . . C5 C 1.7924(3) 0.03414(7) 0.35931(18) 0.0245(5) Uani 1 1 d . . . C6 C 1.6481(3) 0.04920(8) 0.27017(17) 0.0279(5) Uani 1 1 d . . . H6 H 1.5150 0.0598 0.2911 0.033 Uiso 1 1 calc R . . C7 C 1.5287(3) 0.05751(7) 0.62255(18) 0.0259(5) Uani 1 1 d . . . H7 H 1.6194 0.0435 0.6822 0.031 Uiso 1 1 calc R . . C8 C 1.3380(3) 0.08048(7) 0.65674(17) 0.0239(5) Uani 1 1 d . . . C9 C 1.2056(3) 0.10352(7) 0.57347(18) 0.0267(5) Uani 1 1 d . . . H9 H 1.2380 0.1048 0.4909 0.032 Uiso 1 1 calc R . . C10 C 1.0268(3) 0.12455(7) 0.61106(19) 0.0278(5) Uani 1 1 d . . . C11 C 0.9819(3) 0.11968(8) 0.7317(2) 0.0341(6) Uani 1 1 d . . . H11 H 0.8565 0.1319 0.7604 0.041 Uiso 1 1 calc R . . C12 C 1.1211(3) 0.09695(8) 0.8092(2) 0.0347(6) Uani 1 1 d . . . H12 H 1.0894 0.0945 0.8918 0.042 Uiso 1 1 calc R . . C13 C 0.8874(3) 0.15301(9) 0.5270(2) 0.0368(6) Uani 1 1 d . . . H13A H 0.7581 0.1353 0.5072 0.044 Uiso 1 1 calc R . . H13B H 0.8495 0.1825 0.5674 0.044 Uiso 1 1 calc R . . C14 C 0.6041(3) 0.17985(10) 0.2825(2) 0.0516(7) Uani 1 1 d . . . H14A H 0.5801 0.1460 0.2765 0.077 Uiso 1 1 calc R . . H14B H 0.5481 0.1952 0.2088 0.077 Uiso 1 1 calc R . . H14C H 0.5348 0.1923 0.3524 0.077 Uiso 1 1 calc R . . C15 C 1.0220(4) 0.16641(10) 0.1717(2) 0.0527(7) Uani 1 1 d . . . H15A H 1.1711 0.1727 0.1820 0.079 Uiso 1 1 calc R . . H15B H 0.9671 0.1808 0.0965 0.079 Uiso 1 1 calc R . . H15C H 0.9988 0.1325 0.1683 0.079 Uiso 1 1 calc R . . C16 C 1.1699(4) 0.26497(10) 0.3486(3) 0.0618(8) Uani 1 1 d . . . H16A H 1.1935 0.2986 0.3604 0.093 Uiso 1 1 calc R . . H16B H 1.2515 0.2538 0.2822 0.093 Uiso 1 1 calc R . . H16C H 1.2123 0.2482 0.4228 0.093 Uiso 1 1 calc R . . C17 C 0.9377(3) 0.25613(9) 0.3180(2) 0.0387(6) Uani 1 1 d . . . C18 C 0.8766(4) 0.28151(10) 0.2001(2) 0.0638(8) Uani 1 1 d . . . H18A H 0.7277 0.2774 0.1814 0.096 Uiso 1 1 calc R . . H18B H 0.9549 0.2684 0.1345 0.096 Uiso 1 1 calc R . . H18C H 0.9082 0.3149 0.2089 0.096 Uiso 1 1 calc R . . C19 C 0.8127(4) 0.27690(9) 0.4198(2) 0.0582(8) Uani 1 1 d . . . H19A H 0.8538 0.2616 0.4963 0.087 Uiso 1 1 calc R . . H19B H 0.6643 0.2718 0.4014 0.087 Uiso 1 1 calc R . . H19C H 0.8405 0.3106 0.4264 0.087 Uiso 1 1 calc R . . N1 N 1.9803(2) 0.01728(6) 0.33574(15) 0.0278(4) Uani 1 1 d . . . N2 N 1.7500(2) 0.03540(6) 0.48030(15) 0.0276(4) Uani 1 1 d . . . H2 H 1.8358 0.0229 0.5355 0.033 Uiso 1 1 calc R . . N3 N 1.5720(2) 0.05649(6) 0.51084(15) 0.0256(4) Uani 1 1 d . . . N4 N 1.2996(2) 0.07802(6) 0.77472(15) 0.0302(4) Uani 1 1 d . . . O1 O 1.6282(2) 0.06115(9) -0.05994(13) 0.0678(7) Uani 1 1 d . . . H1 H 1.5321 0.0643 -0.1132 0.102 Uiso 1 1 calc R . . O2 O 0.9861(2) 0.16347(6) 0.41996(14) 0.0453(5) Uani 1 1 d . . . Si1 Si 0.88746(9) 0.19134(2) 0.30096(6) 0.0362(2) 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 0.0405(13) 0.0611(19) 0.0214(12) -0.0002(12) -0.0011(10) 0.0136(12) C2 0.0309(11) 0.0325(14) 0.0249(12) 0.0002(10) -0.0005(10) 0.0030(10) C3 0.0358(12) 0.0362(14) 0.0233(12) 0.0022(10) 0.0044(10) 0.0058(10) C4 0.0287(10) 0.0358(14) 0.0302(13) 0.0027(11) 0.0042(10) 0.0063(10) C5 0.0267(10) 0.0232(12) 0.0237(12) 0.0000(9) 0.0018(9) 0.0012(9) C6 0.0249(10) 0.0339(14) 0.0247(12) -0.0013(10) -0.0005(9) 0.0048(10) C7 0.0246(10) 0.0294(13) 0.0234(12) 0.0017(10) -0.0012(9) 0.0042(9) C8 0.0250(10) 0.0242(12) 0.0222(11) -0.0009(9) -0.0015(9) -0.0017(9) C9 0.0284(10) 0.0259(13) 0.0258(12) -0.0002(10) 0.0005(9) -0.0010(9) C10 0.0258(10) 0.0222(12) 0.0352(13) -0.0003(10) 0.0006(10) 0.0003(9) C11 0.0298(11) 0.0345(14) 0.0385(14) -0.0017(11) 0.0077(10) 0.0038(10) C12 0.0363(12) 0.0372(15) 0.0313(13) 0.0016(11) 0.0095(10) 0.0001(11) C13 0.0293(11) 0.0366(14) 0.0447(14) 0.0064(12) 0.0037(11) 0.0064(10) C14 0.0347(12) 0.0499(18) 0.0693(19) 0.0014(15) -0.0076(12) 0.0045(12) C15 0.0493(14) 0.0501(19) 0.0590(18) -0.0042(14) 0.0051(13) 0.0025(13) C16 0.0509(15) 0.0428(18) 0.091(2) 0.0047(16) -0.0064(15) -0.0069(13) C17 0.0385(12) 0.0356(15) 0.0418(15) 0.0060(12) -0.0001(11) 0.0064(11) C18 0.082(2) 0.049(2) 0.061(2) 0.0163(15) 0.0000(16) 0.0148(16) C19 0.0691(17) 0.0410(18) 0.065(2) -0.0046(15) 0.0120(15) 0.0040(14) N1 0.0245(8) 0.0333(11) 0.0259(10) 0.0022(8) 0.0021(8) 0.0047(8) N2 0.0241(8) 0.0361(12) 0.0224(10) 0.0017(8) -0.0007(7) 0.0085(8) N3 0.0212(8) 0.0286(11) 0.0268(10) -0.0015(8) -0.0001(7) 0.0018(7) N4 0.0323(9) 0.0347(12) 0.0237(10) -0.0002(8) 0.0039(8) 0.0019(8) O1 0.0442(10) 0.137(2) 0.0226(10) 0.0118(11) 0.0006(8) 0.0239(12) O2 0.0314(8) 0.0549(12) 0.0498(10) 0.0245(9) 0.0038(8) 0.0098(8) Si1 0.0293(3) 0.0357(4) 0.0431(4) 0.0067(3) -0.0021(3) 0.0061(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 C1 O1 1.395(2) . ? C1 C2 1.493(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C6 1.380(3) . ? C2 C3 1.391(3) . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C4 N1 1.340(2) . ? C4 H4 0.9500 . ? C5 N1 1.342(2) . ? C5 N2 1.383(2) . ? C5 C6 1.392(3) . ? C6 H6 0.9500 . ? C7 N3 1.284(2) . ? C7 C8 1.460(3) . ? C7 H7 0.9500 . ? C8 N4 1.345(2) . ? C8 C9 1.392(3) . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 C11 1.390(3) . ? C10 C13 1.503(3) . ? C11 C12 1.375(3) . ? C11 H11 0.9500 . ? C12 N4 1.345(2) . ? C12 H12 0.9500 . ? C13 O2 1.406(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 Si1 1.859(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 Si1 1.854(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.541(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.529(3) . ? C17 C19 1.538(3) . ? C17 Si1 1.887(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N2 N3 1.355(2) . ? N2 H2 0.8800 . ? O1 H1 0.8400 . ? O2 Si1 1.6425(16) . ? 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 O1 C1 C2 111.70(17) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C6 C2 C3 117.85(19) . . ? C6 C2 C1 120.04(18) . . ? C3 C2 C1 122.11(18) . . ? C4 C3 C2 118.77(19) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? N1 C4 C3 124.55(19) . . ? N1 C4 H4 117.7 . . ? C3 C4 H4 117.7 . . ? N1 C5 N2 114.94(17) . . ? N1 C5 C6 123.48(18) . . ? N2 C5 C6 121.57(17) . . ? C2 C6 C5 119.26(18) . . ? C2 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N3 C7 C8 119.14(18) . . ? N3 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? N4 C8 C9 122.21(18) . . ? N4 C8 C7 115.27(18) . . ? C9 C8 C7 122.52(18) . . ? C10 C9 C8 119.96(19) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 117.6(2) . . ? C9 C10 C13 122.07(19) . . ? C11 C10 C13 120.32(18) . . ? C12 C11 C10 119.23(18) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? N4 C12 C11 123.7(2) . . ? N4 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? O2 C13 C10 110.88(16) . . ? O2 C13 H13A 109.5 . . ? C10 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? Si1 C14 H14A 109.5 . . ? Si1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si1 C15 H15A 109.5 . . ? Si1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C19 108.8(2) . . ? C18 C17 C16 108.5(2) . . ? C19 C17 C16 108.3(2) . . ? C18 C17 Si1 110.10(18) . . ? C19 C17 Si1 111.00(16) . . ? C16 C17 Si1 110.07(17) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C4 N1 C5 115.99(17) . . ? N3 N2 C5 117.68(16) . . ? N3 N2 H2 121.2 . . ? C5 N2 H2 121.2 . . ? C7 N3 N2 118.62(17) . . ? C12 N4 C8 117.21(18) . . ? C1 O1 H1 109.5 . . ? C13 O2 Si1 127.39(12) . . ? O2 Si1 C15 104.91(11) . . ? O2 Si1 C14 110.07(10) . . ? C15 Si1 C14 110.00(12) . . ? O2 Si1 C17 109.70(10) . . ? C15 Si1 C17 111.70(11) . . ? C14 Si1 C17 110.33(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.227 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.057 data_import _database_code_depnum_ccdc_archive 'CCDC 703872' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 N4 O2 Si' _chemical_formula_weight 386.57 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' Si Si 0.0817 0.0704 '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 7.2195(4) _cell_length_b 11.2353(4) _cell_length_c 13.5800(6) _cell_angle_alpha 92.830(3) _cell_angle_beta 102.655(2) _cell_angle_gamma 92.846(3) _cell_volume 1071.38(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5524 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method '/p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7022 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4895 _reflns_number_gt 3296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0885P)^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 4895 _refine_ls_number_parameters 319 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1337 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.2582(3) 0.94823(12) -0.01352(12) 0.0345(4) Uani 1 1 d . . . H1A H 0.1442 0.9275 0.0103 0.041 Uiso 1 1 calc R . . H1B H 0.3659 0.9518 0.0438 0.041 Uiso 1 1 calc R . . C2 C 0.2839(2) 0.85476(13) -0.09156(11) 0.0292(4) Uani 1 1 d . . . C3 C 0.3113(2) 0.88483(14) -0.18550(12) 0.0351(4) Uani 1 1 d . . . H3 H 0.3156 0.9641 -0.2020 0.042 Uiso 1 1 calc R . . C4 C 0.3321(3) 0.79405(14) -0.25365(12) 0.0374(4) Uani 1 1 d . . . H4 H 0.3508 0.8150 -0.3163 0.045 Uiso 1 1 calc R . . C5 C 0.3037(2) 0.65034(13) -0.14478(11) 0.0284(3) Uani 1 1 d . . . C6 C 0.2808(2) 0.73531(13) -0.07059(11) 0.0290(4) Uani 1 1 d . . . H6 H 0.2638 0.7122 -0.0082 0.035 Uiso 1 1 calc R . . C7 C 0.3395(3) 0.43828(14) -0.19996(13) 0.0388(4) Uani 1 1 d . . . H7A H 0.4435 0.3938 -0.1674 0.058 Uiso 1 1 calc R . . H7B H 0.3728 0.4767 -0.2559 0.058 Uiso 1 1 calc R . . H7C H 0.2289 0.3851 -0.2241 0.058 Uiso 1 1 calc R . . C8 C 0.2527(2) 0.38727(13) -0.01891(12) 0.0307(4) Uani 1 1 d . . . H8 H 0.2683 0.3284 -0.0665 0.037 Uiso 1 1 calc R . . C9 C 0.2174(2) 0.35402(13) 0.07823(12) 0.0297(4) Uani 1 1 d . . . C10 C 0.1869(3) 0.20049(14) 0.17988(13) 0.0395(4) Uani 1 1 d . . . H10 H 0.1831 0.1190 0.1892 0.047 Uiso 1 1 calc R . . C11 C 0.1640(3) 0.27688(15) 0.25766(13) 0.0392(4) Uani 1 1 d . . . H11 H 0.1472 0.2477 0.3182 0.047 Uiso 1 1 calc R . . C12 C 0.1666(2) 0.39896(14) 0.24413(12) 0.0344(4) Uani 1 1 d . . . C13 C 0.1922(2) 0.43765(13) 0.15316(12) 0.0312(4) Uani 1 1 d . . . H13 H 0.1927 0.5186 0.1416 0.037 Uiso 1 1 calc R . . C14 C 0.1364(3) 0.48189(15) 0.32835(13) 0.0446(5) Uani 1 1 d . A . H14A H 0.0084 0.4672 0.3382 0.053 Uiso 1 1 calc R . . H14B H 0.2248 0.4661 0.3905 0.053 Uiso 1 1 calc R . . N1 N 0.3272(2) 0.67791(11) -0.23607(10) 0.0344(3) Uani 1 1 d . . . N2 N 0.2993(2) 0.52818(10) -0.12786(9) 0.0308(3) Uani 1 1 d . . . N3 N 0.26219(19) 0.49782(11) -0.03868(9) 0.0292(3) Uani 1 1 d . . . N4 N 0.2145(2) 0.23637(11) 0.09125(10) 0.0349(3) Uani 1 1 d . . . O1 O 0.2430(2) 1.06031(10) -0.05580(9) 0.0565(4) Uani 1 1 d . . . H1 H 0.2359 1.1117 -0.0120 0.085 Uiso 1 1 calc R . . O2 O 0.1635(2) 0.60261(11) 0.30726(9) 0.0493(4) Uani 1 1 d . . . Si1 Si 0.21230(10) 0.70524(5) 0.40156(5) 0.03331(19) Uani 0.77 1 d P A 1 C15 C 0.4370(8) 0.6796(5) 0.4927(3) 0.0582(11) Uani 0.77 1 d P A 1 H15A H 0.4105 0.6269 0.5421 0.087 Uiso 0.77 1 calc PR A 1 H15B H 0.4928 0.7544 0.5260 0.087 Uiso 0.77 1 calc PR A 1 H15C H 0.5239 0.6443 0.4572 0.087 Uiso 0.77 1 calc PR A 1 C16 C 0.0142(9) 0.7053(3) 0.4681(4) 0.0624(12) Uani 0.77 1 d P A 1 H16A H -0.1006 0.7234 0.4220 0.094 Uiso 0.77 1 calc PR A 1 H16B H 0.0433 0.7645 0.5236 0.094 Uiso 0.77 1 calc PR A 1 H16C H -0.0030 0.6281 0.4932 0.094 Uiso 0.77 1 calc PR A 1 C17 C 0.2316(4) 0.84631(19) 0.33492(18) 0.0437(6) Uani 0.77 1 d P A 1 C18 C 0.4123(9) 0.8510(5) 0.2950(4) 0.0813(16) Uani 0.77 1 d P A 1 H18A H 0.4120 0.7818 0.2506 0.122 Uiso 0.77 1 calc PR A 1 H18B H 0.5207 0.8525 0.3506 0.122 Uiso 0.77 1 calc PR A 1 H18C H 0.4185 0.9217 0.2587 0.122 Uiso 0.77 1 calc PR A 1 C19 C 0.0566(5) 0.8514(3) 0.2486(2) 0.0829(11) Uani 0.77 1 d P A 1 H19A H 0.0674 0.9228 0.2137 0.124 Uiso 0.77 1 calc PR A 1 H19B H -0.0557 0.8516 0.2755 0.124 Uiso 0.77 1 calc PR A 1 H19C H 0.0482 0.7829 0.2023 0.124 Uiso 0.77 1 calc PR A 1 C20 C 0.2413(6) 0.9552(2) 0.4085(3) 0.0801(11) Uani 0.77 1 d P A 1 H20A H 0.3454 0.9500 0.4655 0.120 Uiso 0.77 1 calc PR A 1 H20B H 0.1245 0.9573 0.4312 0.120 Uiso 0.77 1 calc PR A 1 H20C H 0.2600 1.0266 0.3749 0.120 Uiso 0.77 1 calc PR A 1 Si1A Si 0.2671(4) 0.7463(2) 0.3526(2) 0.0432(6) Uani 0.23 1 d PD A 2 C17A C 0.1070(12) 0.8353(6) 0.4121(6) 0.0422(19) Uani 0.23 1 d PD A 2 C19A C -0.0482(14) 0.8834(8) 0.3291(7) 0.059(3) Uani 0.23 1 d P A 2 H19D H -0.1363 0.9246 0.3600 0.089 Uiso 0.23 1 calc PR A 2 H19E H -0.1145 0.8180 0.2852 0.089 Uiso 0.23 1 calc PR A 2 H19F H 0.0099 0.9376 0.2906 0.089 Uiso 0.23 1 calc PR A 2 C18A C 0.2214(16) 0.9430(7) 0.4759(7) 0.052(2) Uani 0.23 1 d P A 2 H18D H 0.2581 0.9996 0.4319 0.079 Uiso 0.23 1 calc PR A 2 H18E H 0.3332 0.9162 0.5193 0.079 Uiso 0.23 1 calc PR A 2 H18F H 0.1442 0.9803 0.5163 0.079 Uiso 0.23 1 calc PR A 2 C15A C 0.475(3) 0.6961(17) 0.4508(13) 0.077(5) Uani 0.23 1 d P A 2 H15D H 0.4289 0.6370 0.4899 0.115 Uiso 0.23 1 calc PR A 2 H15E H 0.5337 0.7635 0.4946 0.115 Uiso 0.23 1 calc PR A 2 H15F H 0.5658 0.6625 0.4173 0.115 Uiso 0.23 1 calc PR A 2 C16A C 0.339(3) 0.8299(13) 0.2465(11) 0.070(5) Uani 0.23 1 d P A 2 H16D H 0.4295 0.7861 0.2198 0.106 Uiso 0.23 1 calc PR A 2 H16E H 0.3945 0.9076 0.2725 0.106 Uiso 0.23 1 calc PR A 2 H16F H 0.2282 0.8381 0.1937 0.106 Uiso 0.23 1 calc PR A 2 C20A C 0.011(2) 0.7564(10) 0.4794(12) 0.052(3) Uani 0.23 1 d PD A 2 H20D H -0.0697 0.8033 0.5108 0.078 Uiso 0.23 1 calc PR A 2 H20E H 0.1076 0.7256 0.5307 0.078 Uiso 0.23 1 calc PR A 2 H20F H -0.0628 0.6912 0.4386 0.078 Uiso 0.23 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 C1 0.0404(10) 0.0246(8) 0.0383(9) 0.0021(6) 0.0087(8) 0.0013(7) C2 0.0263(8) 0.0285(8) 0.0312(8) 0.0008(6) 0.0032(6) 0.0003(6) C3 0.0370(10) 0.0283(8) 0.0397(10) 0.0058(7) 0.0078(8) -0.0012(7) C4 0.0434(11) 0.0368(9) 0.0332(9) 0.0061(7) 0.0111(8) -0.0028(8) C5 0.0258(9) 0.0275(8) 0.0305(8) 0.0011(6) 0.0043(6) -0.0005(6) C6 0.0288(9) 0.0298(8) 0.0278(8) 0.0025(6) 0.0053(6) -0.0003(7) C7 0.0488(11) 0.0323(8) 0.0372(9) -0.0057(7) 0.0155(8) 0.0022(8) C8 0.0292(9) 0.0262(8) 0.0354(9) -0.0037(6) 0.0055(7) 0.0011(6) C9 0.0248(8) 0.0255(7) 0.0374(9) 0.0023(6) 0.0041(7) 0.0003(6) C10 0.0386(10) 0.0307(8) 0.0504(11) 0.0124(8) 0.0098(8) 0.0032(7) C11 0.0355(10) 0.0436(10) 0.0398(10) 0.0126(7) 0.0086(8) 0.0029(8) C12 0.0272(9) 0.0401(9) 0.0345(9) 0.0015(7) 0.0038(7) 0.0022(7) C13 0.0291(9) 0.0263(8) 0.0365(9) 0.0015(6) 0.0040(7) 0.0017(6) C14 0.0499(12) 0.0457(10) 0.0383(10) 0.0011(8) 0.0110(9) 0.0013(9) N1 0.0378(8) 0.0344(7) 0.0313(7) -0.0001(5) 0.0097(6) -0.0014(6) N2 0.0366(8) 0.0266(7) 0.0295(7) -0.0012(5) 0.0091(6) 0.0015(6) N3 0.0285(7) 0.0276(6) 0.0313(7) 0.0009(5) 0.0068(6) 0.0000(5) N4 0.0342(8) 0.0263(7) 0.0441(8) 0.0040(6) 0.0079(6) 0.0018(6) O1 0.0978(12) 0.0285(6) 0.0460(8) 0.0062(5) 0.0189(8) 0.0163(7) O2 0.0614(9) 0.0451(7) 0.0413(7) -0.0113(5) 0.0163(6) -0.0052(6) Si1 0.0395(4) 0.0321(3) 0.0278(3) -0.0006(2) 0.0069(3) 0.0021(3) C15 0.055(3) 0.059(2) 0.053(3) -0.0038(18) -0.0059(18) 0.0152(19) C16 0.074(3) 0.068(3) 0.052(2) -0.004(2) 0.0308(18) 0.000(3) C17 0.0534(16) 0.0278(11) 0.0463(14) -0.0005(9) 0.0053(12) -0.0044(10) C18 0.094(4) 0.067(3) 0.095(4) 0.017(3) 0.048(3) -0.011(2) C19 0.102(3) 0.0478(16) 0.078(2) 0.0286(15) -0.026(2) -0.0143(17) C20 0.122(3) 0.0377(15) 0.071(2) -0.0116(15) 0.006(2) -0.0024(17) Si1A 0.0501(15) 0.0344(12) 0.0510(14) 0.0008(11) 0.0249(12) 0.0013(10) C17A 0.055(5) 0.029(4) 0.039(4) -0.001(3) 0.004(4) 0.002(4) C19A 0.062(6) 0.046(5) 0.061(6) 0.007(4) -0.011(5) 0.022(5) C18A 0.066(7) 0.041(5) 0.043(5) -0.009(4) 0.000(5) 0.006(4) C15A 0.051(8) 0.065(9) 0.106(16) -0.021(10) 0.007(10) 0.010(7) C16A 0.126(18) 0.032(6) 0.075(11) 0.010(7) 0.070(10) 0.000(8) C20A 0.036(6) 0.076(10) 0.048(7) -0.001(8) 0.022(5) -0.005(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 C1 O1 1.4089(16) . ? C1 C2 1.502(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C6 1.386(2) . ? C2 C3 1.388(2) . ? C3 C4 1.379(2) . ? C3 H3 0.9300 . ? C4 N1 1.3382(19) . ? C4 H4 0.9300 . ? C5 N1 1.337(2) . ? C5 C6 1.395(2) . ? C5 N2 1.4026(18) . ? C6 H6 0.9300 . ? C7 N2 1.4559(19) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N3 1.2853(18) . ? C8 C9 1.460(2) . ? C8 H8 0.9300 . ? C9 N4 1.3421(19) . ? C9 C13 1.398(2) . ? C10 N4 1.340(2) . ? C10 C11 1.371(2) . ? C10 H10 0.9300 . ? C11 C12 1.393(2) . ? C11 H11 0.9300 . ? C12 C13 1.376(2) . ? C12 C14 1.499(2) . ? C13 H13 0.9300 . ? C14 O2 1.413(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N2 N3 1.3523(17) . ? O1 H1 0.8200 . ? O2 Si1 1.6462(13) . ? O2 Si1A 1.767(3) . ? Si1 C16 1.852(4) . ? Si1 C15 1.857(5) . ? Si1 C17 1.878(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.518(7) . ? C17 C19 1.529(4) . ? C17 C20 1.530(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Si1A C17A 1.853(8) . ? Si1A C15A 1.903(19) . ? Si1A C16A 1.908(16) . ? C17A C18A 1.543(12) . ? C17A C19A 1.544(11) . ? C17A C20A 1.547(8) . ? C19A H19D 0.9600 . ? C19A H19E 0.9600 . ? C19A H19F 0.9600 . ? C18A H18D 0.9600 . ? C18A H18E 0.9600 . ? C18A H18F 0.9600 . ? C15A H15D 0.9600 . ? C15A H15E 0.9600 . ? C15A H15F 0.9600 . ? C16A H16D 0.9600 . ? C16A H16E 0.9600 . ? C16A H16F 0.9600 . ? C20A H20D 0.9600 . ? C20A H20E 0.9600 . ? C20A H20F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 109.82(12) . . ? O1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? O1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C6 C2 C3 118.41(14) . . ? C6 C2 C1 120.06(13) . . ? C3 C2 C1 121.53(13) . . ? C4 C3 C2 118.25(14) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? N1 C4 C3 124.68(15) . . ? N1 C4 H4 117.7 . . ? C3 C4 H4 117.7 . . ? N1 C5 C6 123.38(14) . . ? N1 C5 N2 115.52(13) . . ? C6 C5 N2 121.09(14) . . ? C2 C6 C5 118.82(14) . . ? C2 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 120.04(13) . . ? N3 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? N4 C9 C13 122.17(14) . . ? N4 C9 C8 114.76(13) . . ? C13 C9 C8 123.05(14) . . ? N4 C10 C11 123.83(15) . . ? N4 C10 H10 118.1 . . ? C11 C10 H10 118.1 . . ? C10 C11 C12 118.67(15) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 118.46(15) . . ? C13 C12 C14 123.03(14) . . ? C11 C12 C14 118.48(15) . . ? C12 C13 C9 119.31(14) . . ? C12 C13 H13 120.3 . . ? C9 C13 H13 120.3 . . ? O2 C14 C12 111.41(14) . . ? O2 C14 H14A 109.3 . . ? C12 C14 H14A 109.3 . . ? O2 C14 H14B 109.3 . . ? C12 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C5 N1 C4 116.44(13) . . ? N3 N2 C5 116.42(12) . . ? N3 N2 C7 121.14(12) . . ? C5 N2 C7 122.40(13) . . ? C8 N3 N2 119.75(13) . . ? C10 N4 C9 117.55(14) . . ? C1 O1 H1 109.5 . . ? C14 O2 Si1 119.03(11) . . ? C14 O2 Si1A 147.02(15) . . ? Si1 O2 Si1A 32.72(8) . . ? O2 Si1 C16 109.47(17) . . ? O2 Si1 C15 111.78(17) . . ? C16 Si1 C15 109.4(2) . . ? O2 Si1 C17 102.40(9) . . ? C16 Si1 C17 111.67(17) . . ? C15 Si1 C17 111.93(18) . . ? C18 C17 C19 110.7(3) . . ? C18 C17 C20 107.8(3) . . ? C19 C17 C20 108.7(2) . . ? C18 C17 Si1 109.9(2) . . ? C19 C17 Si1 109.42(17) . . ? C20 C17 Si1 110.18(18) . . ? O2 Si1A C17A 112.1(3) . . ? O2 Si1A C15A 97.2(6) . . ? C17A Si1A C15A 111.6(6) . . ? O2 Si1A C16A 110.7(4) . . ? C17A Si1A C16A 110.1(6) . . ? C15A Si1A C16A 114.6(8) . . ? C18A C17A C19A 108.1(6) . . ? C18A C17A C20A 110.2(8) . . ? C19A C17A C20A 109.2(10) . . ? C18A C17A Si1A 109.8(6) . . ? C19A C17A Si1A 109.6(6) . . ? C20A C17A Si1A 109.9(6) . . ? C17A C19A H19D 109.5 . . ? C17A C19A H19E 109.5 . . ? H19D C19A H19E 109.5 . . ? C17A C19A H19F 109.5 . . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? C17A C18A H18D 109.5 . . ? C17A C18A H18E 109.5 . . ? H18D C18A H18E 109.5 . . ? C17A C18A H18F 109.5 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? Si1A C15A H15D 109.5 . . ? Si1A C15A H15E 109.5 . . ? H15D C15A H15E 109.5 . . ? Si1A C15A H15F 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? Si1A C16A H16D 109.5 . . ? Si1A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? Si1A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C17A C20A H20D 109.5 . . ? C17A C20A H20E 109.5 . . ? H20D C20A H20E 109.5 . . ? C17A C20A H20F 109.5 . . ? H20D C20A H20F 109.5 . . ? H20E C20A H20F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.284 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.048 data_su26 _database_code_depnum_ccdc_archive 'CCDC 703873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 F6 N4 O8 Pb S2' _chemical_formula_weight 773.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 '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 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 10.2401(3) _cell_length_b 13.1113(6) _cell_length_c 17.6193(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.972(2) _cell_angle_gamma 90.00 _cell_volume 2336.64(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9565 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 7.498 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1364 _exptl_absorpt_correction_T_max 0.1865 _exptl_absorpt_process_details wingx _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method 'phi&omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14425 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5341 _reflns_number_gt 4032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^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 5341 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 C1 C -0.0886(5) 0.7188(5) -0.0270(3) 0.0438(14) Uani 1 1 d . . . C2 C 0.2991(6) 0.9461(6) 0.4092(4) 0.0546(18) Uani 1 1 d . . . C3 C 0.3841(5) 1.1689(4) 0.2018(3) 0.0346(12) Uani 1 1 d . . . H3 H 0.4108 1.2340 0.2223 0.042 Uiso 1 1 calc R . . C4 C 0.4788(5) 1.1102(4) 0.1637(3) 0.0319(12) Uani 1 1 d . . . C5 C 0.6011(5) 1.1515(5) 0.1594(3) 0.0366(13) Uani 1 1 d . . . H5 H 0.6262 1.2161 0.1813 0.044 Uiso 1 1 calc R . . C6 C 0.6860(5) 1.0952(5) 0.1219(3) 0.0398(13) Uani 1 1 d . . . H6 H 0.7696 1.1227 0.1159 0.048 Uiso 1 1 calc R . . C7 C 0.6511(5) 1.0006(5) 0.0936(3) 0.0367(13) Uani 1 1 d . . . H7 H 0.7097 0.9621 0.0681 0.044 Uiso 1 1 calc R . . C8 C 0.5270(5) 0.9612(4) 0.1029(3) 0.0303(12) Uani 1 1 d . . . C9 C 0.5700(5) 0.7953(4) 0.0401(3) 0.0475(15) Uani 1 1 d . . . H9A H 0.6233 0.7526 0.0789 0.071 Uiso 1 1 calc R . . H9B H 0.6284 0.8356 0.0128 0.071 Uiso 1 1 calc R . . H9C H 0.5136 0.7517 0.0035 0.071 Uiso 1 1 calc R . . C10 C 0.3585(4) 0.7288(4) 0.1026(3) 0.0287(11) Uani 1 1 d . . . H10 H 0.4119 0.6854 0.0770 0.034 Uiso 1 1 calc R . . C11 C 0.2498(5) 0.6863(4) 0.1374(3) 0.0286(11) Uani 1 1 d . . . C12 C 0.2257(5) 0.5819(4) 0.1369(3) 0.0355(13) Uani 1 1 d . . . H12 H 0.2774 0.5370 0.1114 0.043 Uiso 1 1 calc R . . C13 C 0.1264(6) 0.5438(4) 0.1734(3) 0.0417(14) Uani 1 1 d . . . H13 H 0.1087 0.4727 0.1738 0.050 Uiso 1 1 calc R . . C14 C 0.0537(5) 0.6120(4) 0.2092(3) 0.0378(13) Uani 1 1 d . . . H14 H -0.0145 0.5879 0.2355 0.045 Uiso 1 1 calc R . . C15 C 0.0793(5) 0.7141(4) 0.2069(3) 0.0305(11) Uani 1 1 d . . . C16 C -0.0007(5) 0.7890(4) 0.2410(3) 0.0382(13) Uani 1 1 d . . . H16 H -0.0703 0.7647 0.2660 0.046 Uiso 1 1 calc R . . F1 F 0.0073(4) 0.6544(3) -0.0332(3) 0.0906(14) Uani 1 1 d . . . F2 F -0.1243(4) 0.7003(3) 0.0407(2) 0.0822(13) Uani 1 1 d . . . F3 F -0.1902(4) 0.6959(3) -0.0792(2) 0.0801(13) Uani 1 1 d . . . F4 F 0.2624(4) 0.8511(4) 0.4228(2) 0.0779(12) Uani 1 1 d . . . F5 F 0.3497(4) 0.9881(4) 0.4766(2) 0.0873(14) Uani 1 1 d . . . F6 F 0.1942(4) 0.9979(4) 0.3802(3) 0.0868(14) Uani 1 1 d . . . N1 N 0.4418(4) 1.0165(3) 0.1369(2) 0.0274(9) Uani 1 1 d . . . N2 N 0.4874(4) 0.8635(3) 0.0777(2) 0.0309(10) Uani 1 1 d . . . N3 N 0.3814(4) 0.8241(3) 0.1066(2) 0.0282(9) Uani 1 1 d . . . N4 N 0.1782(4) 0.7523(3) 0.1716(2) 0.0270(9) Uani 1 1 d . . . O1 O 0.0728(5) 0.8577(4) 0.0269(3) 0.0791(16) Uani 1 1 d . . . O2 O -0.1545(4) 0.9070(3) -0.0246(3) 0.0573(12) Uani 1 1 d . . . O3 O -0.0027(3) 0.8605(4) -0.1088(2) 0.0535(11) Uani 1 1 d . . . O4 O 0.3496(4) 0.9024(3) 0.2756(2) 0.0425(9) Uani 1 1 d . . . O5 O 0.4582(4) 1.0514(3) 0.3395(2) 0.0559(12) Uani 1 1 d . . . O6 O 0.5236(3) 0.8808(3) 0.3831(2) 0.0483(10) Uani 1 1 d . . . O7 O 0.2738(3) 1.1389(3) 0.2086(2) 0.0370(9) Uani 1 1 d . . . O8 O 0.0175(4) 0.8806(3) 0.2389(2) 0.0489(11) Uani 1 1 d . . . Pb1 Pb 0.209974(16) 0.947223(14) 0.150548(10) 0.02579(7) Uani 1 1 d . . . S1 S -0.03744(13) 0.85062(11) -0.03321(8) 0.0375(3) Uani 1 1 d . . . S2 S 0.42295(13) 0.94675(11) 0.34543(7) 0.0338(3) 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 0.039(3) 0.042(4) 0.050(4) 0.001(3) 0.005(3) 0.000(3) C2 0.050(4) 0.063(5) 0.049(4) -0.009(4) 0.005(3) 0.012(4) C3 0.040(3) 0.027(3) 0.035(3) 0.000(2) 0.002(2) -0.004(2) C4 0.032(3) 0.030(3) 0.033(3) 0.008(2) 0.004(2) -0.004(2) C5 0.036(3) 0.039(3) 0.036(3) -0.001(3) 0.007(2) -0.012(3) C6 0.034(3) 0.044(4) 0.042(3) 0.006(3) 0.008(2) -0.013(3) C7 0.030(3) 0.045(4) 0.038(3) 0.000(3) 0.015(2) -0.005(3) C8 0.029(3) 0.039(3) 0.023(3) 0.005(2) 0.003(2) 0.000(2) C9 0.051(3) 0.040(4) 0.057(4) -0.009(3) 0.026(3) -0.001(3) C10 0.025(2) 0.025(3) 0.036(3) 0.001(2) 0.007(2) 0.006(2) C11 0.034(3) 0.026(3) 0.026(3) -0.004(2) 0.004(2) -0.001(2) C12 0.045(3) 0.024(3) 0.039(3) -0.005(2) 0.014(3) -0.001(2) C13 0.052(3) 0.028(3) 0.046(3) 0.003(3) 0.012(3) -0.007(3) C14 0.043(3) 0.034(3) 0.038(3) 0.000(3) 0.011(2) -0.008(3) C15 0.034(3) 0.031(3) 0.027(3) 0.001(2) 0.007(2) -0.003(2) C16 0.046(3) 0.035(4) 0.037(3) 0.000(3) 0.018(2) -0.002(3) F1 0.061(2) 0.038(2) 0.173(5) -0.017(3) 0.019(3) 0.011(2) F2 0.120(3) 0.060(3) 0.072(3) 0.026(2) 0.030(2) -0.009(2) F3 0.064(2) 0.062(3) 0.102(3) 0.006(2) -0.025(2) -0.023(2) F4 0.076(3) 0.084(3) 0.082(3) 0.008(3) 0.038(2) -0.018(2) F5 0.081(3) 0.139(4) 0.043(2) -0.036(3) 0.0164(19) -0.006(3) F6 0.055(2) 0.107(4) 0.096(3) -0.023(3) 0.006(2) 0.033(3) N1 0.029(2) 0.027(2) 0.027(2) 0.0061(19) 0.0062(17) -0.0003(19) N2 0.031(2) 0.029(3) 0.037(2) -0.002(2) 0.0182(18) -0.0034(19) N3 0.028(2) 0.029(3) 0.028(2) 0.0032(19) 0.0040(16) -0.0021(18) N4 0.030(2) 0.024(2) 0.025(2) -0.0018(18) 0.0014(16) 0.0012(18) O1 0.111(4) 0.047(3) 0.062(3) 0.004(2) -0.041(3) -0.016(3) O2 0.082(3) 0.035(2) 0.066(3) 0.014(2) 0.046(2) 0.016(2) O3 0.041(2) 0.081(3) 0.041(2) 0.006(2) 0.0146(17) -0.008(2) O4 0.057(2) 0.040(2) 0.028(2) -0.0034(18) 0.0000(17) -0.012(2) O5 0.072(3) 0.037(3) 0.052(3) 0.006(2) -0.011(2) -0.017(2) O6 0.043(2) 0.050(3) 0.048(2) -0.004(2) -0.0028(18) 0.006(2) O7 0.0347(19) 0.035(2) 0.041(2) -0.0011(18) 0.0052(16) 0.0027(17) O8 0.057(2) 0.033(3) 0.064(3) -0.003(2) 0.035(2) 0.001(2) Pb1 0.02382(11) 0.02500(11) 0.02922(11) 0.00006(9) 0.00628(7) 0.00029(8) S1 0.0442(7) 0.0334(8) 0.0336(7) 0.0010(6) 0.0016(6) -0.0009(7) S2 0.0354(7) 0.0346(8) 0.0300(7) -0.0012(6) 0.0008(5) -0.0038(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 C1 F1 1.312(6) . ? C1 F3 1.312(6) . ? C1 F2 1.323(7) . ? C1 S1 1.815(6) . ? C2 F6 1.306(7) . ? C2 F4 1.335(7) . ? C2 F5 1.338(7) . ? C2 S2 1.821(7) . ? C3 O7 1.219(5) . ? C3 C4 1.479(7) . ? C3 H3 0.9500 . ? C4 N1 1.349(7) . ? C4 C5 1.377(7) . ? C5 C6 1.384(7) . ? C5 H5 0.9500 . ? C6 C7 1.363(8) . ? C6 H6 0.9500 . ? C7 C8 1.405(7) . ? C7 H7 0.9500 . ? C8 N1 1.345(6) . ? C8 N2 1.395(6) . ? C9 N2 1.460(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N3 1.270(6) . ? C10 C11 1.462(7) . ? C10 H10 0.9500 . ? C11 N4 1.336(6) . ? C11 C12 1.392(7) . ? C12 C13 1.378(7) . ? C12 H12 0.9500 . ? C13 C14 1.378(8) . ? C13 H13 0.9500 . ? C14 C15 1.366(7) . ? C14 H14 0.9500 . ? C15 N4 1.364(6) . ? C15 C16 1.466(7) . ? C16 O8 1.217(6) . ? C16 H16 0.9500 . ? N1 Pb1 2.587(4) . ? N2 N3 1.370(5) . ? N3 Pb1 2.590(4) . ? N4 Pb1 2.611(4) . ? O1 S1 1.426(4) . ? O1 Pb1 2.672(4) . ? O2 S1 1.436(4) . ? O3 S1 1.437(4) . ? O4 S2 1.459(4) . ? O4 Pb1 2.502(3) . ? O5 S2 1.427(4) . ? O6 S2 1.428(4) . ? O7 Pb1 2.754(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 F1 C1 F3 108.5(5) . . ? F1 C1 F2 105.8(5) . . ? F3 C1 F2 106.9(5) . . ? F1 C1 S1 112.4(4) . . ? F3 C1 S1 112.3(4) . . ? F2 C1 S1 110.6(4) . . ? F6 C2 F4 108.5(6) . . ? F6 C2 F5 108.4(6) . . ? F4 C2 F5 107.9(6) . . ? F6 C2 S2 111.4(5) . . ? F4 C2 S2 111.0(4) . . ? F5 C2 S2 109.6(5) . . ? O7 C3 C4 124.1(5) . . ? O7 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? N1 C4 C5 123.1(5) . . ? N1 C4 C3 117.7(4) . . ? C5 C4 C3 119.1(5) . . ? C4 C5 C6 117.5(5) . . ? C4 C5 H5 121.3 . . ? C6 C5 H5 121.3 . . ? C7 C6 C5 120.7(5) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 118.8(5) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? N1 C8 N2 117.4(4) . . ? N1 C8 C7 121.0(5) . . ? N2 C8 C7 121.6(5) . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 C11 119.8(5) . . ? N3 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N4 C11 C12 122.0(5) . . ? N4 C11 C10 116.7(4) . . ? C12 C11 C10 121.2(5) . . ? C13 C12 C11 119.8(5) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 118.0(5) . . ? C14 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C15 C14 C13 120.1(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? N4 C15 C14 122.2(5) . . ? N4 C15 C16 116.3(5) . . ? C14 C15 C16 121.5(5) . . ? O8 C16 C15 123.5(5) . . ? O8 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? C8 N1 C4 118.7(4) . . ? C8 N1 Pb1 121.4(3) . . ? C4 N1 Pb1 119.9(3) . . ? N3 N2 C8 115.9(4) . . ? N3 N2 C9 119.1(4) . . ? C8 N2 C9 123.2(4) . . ? C10 N3 N2 120.0(4) . . ? C10 N3 Pb1 120.1(3) . . ? N2 N3 Pb1 119.2(3) . . ? C11 N4 C15 117.8(4) . . ? C11 N4 Pb1 118.7(3) . . ? C15 N4 Pb1 122.8(3) . . ? S1 O1 Pb1 152.7(3) . . ? S2 O4 Pb1 142.8(2) . . ? C3 O7 Pb1 115.3(3) . . ? O4 Pb1 N1 76.00(12) . . ? O4 Pb1 N3 78.21(12) . . ? N1 Pb1 N3 61.11(13) . . ? O4 Pb1 N4 73.24(12) . . ? N1 Pb1 N4 119.57(12) . . ? N3 Pb1 N4 62.44(12) . . ? O4 Pb1 O1 140.35(14) . . ? N1 Pb1 O1 116.84(15) . . ? N3 Pb1 O1 77.13(14) . . ? N4 Pb1 O1 67.93(13) . . ? O4 Pb1 O7 79.48(11) . . ? N1 Pb1 O7 63.01(11) . . ? N3 Pb1 O7 123.18(11) . . ? N4 Pb1 O7 150.29(11) . . ? O1 Pb1 O7 140.17(12) . . ? O1 S1 O2 117.7(3) . . ? O1 S1 O3 113.6(3) . . ? O2 S1 O3 112.5(2) . . ? O1 S1 C1 102.7(3) . . ? O2 S1 C1 103.3(3) . . ? O3 S1 C1 104.9(3) . . ? O5 S2 O6 116.4(2) . . ? O5 S2 O4 115.1(2) . . ? O6 S2 O4 112.9(2) . . ? O5 S2 C2 105.0(3) . . ? O6 S2 C2 103.4(3) . . ? O4 S2 C2 101.7(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.311 _refine_diff_density_min -1.623 _refine_diff_density_rms 0.150 data_su18 _database_code_depnum_ccdc_archive 'CCDC 703874' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 F6 N6 O8 Pb S2' _chemical_formula_weight 885.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 '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 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 8.7467(2) _cell_length_b 13.0859(5) _cell_length_c 26.4906(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.775(2) _cell_angle_gamma 90.00 _cell_volume 3004.20(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19325 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.958 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 5.848 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5538 _exptl_absorpt_correction_T_max 0.6088 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method '/p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16909 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6841 _reflns_number_gt 4398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The restrains were used on the anisotropic displacement parameters of the -CF3 fragment, F4, F5, F6, C22, of one triflate anion. ; _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^+27.4154P] 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 6841 _refine_ls_number_parameters 407 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1056 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0437(11) 0.8932(8) 0.4283(4) 0.042(2) Uani 1 1 d . . . C2 C -0.0687(11) 0.9666(8) 0.4325(4) 0.050(3) Uani 1 1 d . . . H2 H -0.1480 0.9545 0.4530 0.060 Uiso 1 1 calc R . . C3 C -0.0627(13) 1.0569(9) 0.4065(4) 0.058(3) Uani 1 1 d . . . H3 H -0.1360 1.1091 0.4100 0.070 Uiso 1 1 calc R . . C4 C 0.0468(11) 1.0716(8) 0.3763(4) 0.047(2) Uani 1 1 d . . . H4 H 0.0509 1.1337 0.3579 0.057 Uiso 1 1 calc R . . C5 C 0.1553(10) 0.9935(7) 0.3721(4) 0.039(2) Uani 1 1 d . . . C6 C 0.2648(14) 1.0886(9) 0.3014(4) 0.068(3) Uani 1 1 d . . . H6A H 0.3218 1.1481 0.3165 0.102 Uiso 1 1 calc R . . H6B H 0.1572 1.1079 0.2903 0.102 Uiso 1 1 calc R . . H6C H 0.3119 1.0646 0.2721 0.102 Uiso 1 1 calc R . . C7 C 0.5050(10) 0.9574(7) 0.3208(3) 0.040(2) Uani 1 1 d . . . H7 H 0.5086 1.0182 0.3014 0.048 Uiso 1 1 calc R . . C8 C 0.6287(10) 0.8839(7) 0.3232(4) 0.040(2) Uani 1 1 d . . . C9 C 0.7606(11) 0.9070(8) 0.3002(4) 0.050(3) Uani 1 1 d . . . H9 H 0.7688 0.9707 0.2835 0.061 Uiso 1 1 calc R . . C10 C 0.8773(12) 0.8359(9) 0.3022(4) 0.057(3) Uani 1 1 d . . . H10 H 0.9666 0.8501 0.2866 0.069 Uiso 1 1 calc R . . C11 C 0.8650(9) 0.7462(7) 0.3263(3) 0.0347(19) Uani 1 1 d . . . H11 H 0.9462 0.6975 0.3285 0.042 Uiso 1 1 calc R . . C12 C 0.7317(11) 0.7260(7) 0.3478(4) 0.042(2) Uani 1 1 d . . . C13 C 0.7061(10) 0.6273(8) 0.3720(4) 0.045(2) Uani 1 1 d . . . H13 H 0.7844 0.5765 0.3743 0.054 Uiso 1 1 calc R . . C14 C 0.5564(12) 0.5067(7) 0.4088(4) 0.052(3) Uani 1 1 d . . . H14A H 0.5313 0.5109 0.4441 0.062 Uiso 1 1 calc R . . H14B H 0.6505 0.4645 0.4091 0.062 Uiso 1 1 calc R . . C15 C 0.4231(12) 0.4587(7) 0.3742(4) 0.050(3) Uani 1 1 d . . . H15A H 0.4541 0.4445 0.3403 0.060 Uiso 1 1 calc R . . H15B H 0.3928 0.3935 0.3890 0.060 Uiso 1 1 calc R . . C16 C 0.1542(13) 0.4806(9) 0.3530(4) 0.060(3) Uani 1 1 d . . . H16A H 0.1706 0.4225 0.3304 0.072 Uiso 1 1 calc R . . H16B H 0.0838 0.5298 0.3332 0.072 Uiso 1 1 calc R . . C17 C 0.0808(12) 0.4422(8) 0.3980(4) 0.051(3) Uani 1 1 d . . . H17A H -0.0148 0.4043 0.3856 0.061 Uiso 1 1 calc R . . H17B H 0.1525 0.3946 0.4183 0.061 Uiso 1 1 calc R . . C18 C 0.1631(11) 0.5454(8) 0.4710(4) 0.047(2) Uani 1 1 d . . . H18A H 0.2647 0.5468 0.4585 0.056 Uiso 1 1 calc R . . H18B H 0.1651 0.4905 0.4968 0.056 Uiso 1 1 calc R . . C19 C 0.1333(11) 0.6453(7) 0.4943(4) 0.041(2) Uani 1 1 d . . . H19A H 0.0297 0.6442 0.5054 0.050 Uiso 1 1 calc R . . H19B H 0.2103 0.6563 0.5248 0.050 Uiso 1 1 calc R . . C20 C 0.0383(11) 0.8001(7) 0.4578(3) 0.041(2) Uani 1 1 d . . . H20 H -0.0444 0.7909 0.4772 0.049 Uiso 1 1 calc R . . C21 C 0.5051(14) 0.8567(9) 0.5474(4) 0.056(3) Uani 1 1 d . . . C22 C 0.274(3) 0.7885(17) 0.2073(6) 0.116(5) Uani 1 1 d U . . F1 F 0.3585(8) 0.8726(6) 0.5299(3) 0.096(3) Uani 1 1 d . . . F2 F 0.5743(8) 0.9470(5) 0.5502(2) 0.0677(18) Uani 1 1 d . . . F3 F 0.5161(11) 0.8208(6) 0.5942(3) 0.100(3) Uani 1 1 d . . . F4 F 0.1642(18) 0.8543(11) 0.2043(4) 0.190(5) Uani 1 1 d U . . F5 F 0.2786(12) 0.7521(8) 0.1608(3) 0.122(3) Uani 1 1 d U . . F6 F 0.4087(14) 0.8338(9) 0.2195(3) 0.153(4) Uani 1 1 d U . . N1 N 0.1555(8) 0.9071(5) 0.3983(3) 0.0358(17) Uani 1 1 d . . . N2 N 0.2701(8) 1.0056(6) 0.3400(3) 0.0412(19) Uani 1 1 d . . . N3 N 0.3895(8) 0.9404(5) 0.3452(3) 0.0356(17) Uani 1 1 d . . . N4 N 0.6142(9) 0.7944(6) 0.3464(3) 0.0404(18) Uani 1 1 d . . . N5 N 0.5824(8) 0.6089(6) 0.3896(3) 0.0391(18) Uani 1 1 d . . . N6 N 0.1415(9) 0.7294(6) 0.4587(3) 0.0411(19) Uani 1 1 d . . . O1 O 0.5724(10) 0.8233(6) 0.4583(3) 0.066(2) Uani 1 1 d . . . O2 O 0.5050(8) 0.6777(5) 0.5066(3) 0.0541(18) Uani 1 1 d . . . O3 O 0.7500(8) 0.7640(6) 0.5299(3) 0.071(2) Uani 1 1 d . . . O4 O 0.2330(9) 0.7561(6) 0.2974(3) 0.063(2) Uani 1 1 d . . . O5 O 0.1211(11) 0.6356(8) 0.2348(4) 0.095(3) Uani 1 1 d . . . O6 O 0.3936(11) 0.6348(9) 0.2577(4) 0.108(4) Uani 1 1 d . . . O7 O 0.2969(7) 0.5286(5) 0.3694(3) 0.0460(16) Uani 1 1 d . . . O8 O 0.0448(7) 0.5251(5) 0.4297(3) 0.0488(17) Uani 1 1 d . . . Pb1 Pb 0.36796(4) 0.75480(3) 0.389291(13) 0.03922(13) Uani 1 1 d . . . S1 S 0.5939(3) 0.76983(18) 0.50648(9) 0.0425(6) Uani 1 1 d . . . S2 S 0.2502(4) 0.6918(3) 0.25452(12) 0.0696(9) 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 0.035(5) 0.048(6) 0.045(6) -0.004(5) 0.010(4) -0.003(4) C2 0.036(5) 0.062(7) 0.055(6) -0.010(5) 0.015(5) 0.017(5) C3 0.052(7) 0.071(8) 0.052(7) 0.001(6) 0.009(5) 0.018(6) C4 0.046(6) 0.045(6) 0.049(6) 0.004(5) 0.000(5) 0.011(5) C5 0.034(5) 0.042(5) 0.041(5) -0.005(4) 0.004(4) -0.004(4) C6 0.073(8) 0.069(8) 0.067(8) 0.020(6) 0.025(7) 0.013(7) C7 0.041(5) 0.039(5) 0.043(5) 0.001(4) 0.014(4) -0.011(4) C8 0.036(5) 0.043(5) 0.041(5) -0.007(4) 0.008(4) -0.007(4) C9 0.045(6) 0.056(6) 0.055(7) -0.004(5) 0.021(5) -0.018(5) C10 0.038(6) 0.075(8) 0.062(7) -0.003(6) 0.018(5) -0.009(6) C11 0.023(4) 0.050(5) 0.029(4) -0.003(4) -0.002(3) 0.018(4) C12 0.036(5) 0.049(6) 0.040(5) -0.005(4) 0.004(4) 0.003(4) C13 0.027(5) 0.052(6) 0.057(6) -0.003(5) 0.010(4) 0.008(4) C14 0.047(6) 0.041(6) 0.070(7) 0.007(5) 0.018(5) 0.009(5) C15 0.055(6) 0.035(5) 0.065(7) 0.003(5) 0.024(6) 0.007(5) C16 0.063(7) 0.054(7) 0.064(8) 0.003(6) 0.008(6) 0.005(6) C17 0.040(6) 0.050(6) 0.060(7) -0.002(5) 0.002(5) -0.011(5) C18 0.036(5) 0.055(6) 0.050(6) 0.013(5) 0.006(5) -0.009(5) C19 0.035(5) 0.052(6) 0.040(5) 0.005(4) 0.013(4) -0.007(4) C20 0.036(5) 0.049(6) 0.040(5) 0.009(4) 0.009(4) 0.005(5) C21 0.067(8) 0.056(7) 0.049(7) -0.011(5) 0.018(6) -0.003(6) C22 0.145(11) 0.145(11) 0.052(7) -0.001(8) -0.008(8) 0.019(9) F1 0.046(4) 0.106(6) 0.137(7) -0.057(5) 0.018(4) 0.010(4) F2 0.078(5) 0.054(4) 0.068(4) -0.016(3) -0.003(3) -0.007(3) F3 0.158(8) 0.097(6) 0.056(5) -0.013(4) 0.052(5) -0.020(6) F4 0.264(13) 0.207(12) 0.097(7) 0.036(8) 0.013(8) 0.127(10) F5 0.129(7) 0.181(9) 0.059(5) -0.031(5) 0.025(5) -0.028(6) F6 0.185(10) 0.199(10) 0.079(6) 0.000(6) 0.030(6) -0.118(8) N1 0.029(4) 0.034(4) 0.046(5) -0.003(3) 0.011(3) -0.001(3) N2 0.030(4) 0.044(5) 0.048(5) 0.004(4) 0.002(4) -0.002(4) N3 0.038(4) 0.034(4) 0.034(4) 0.003(3) 0.001(3) -0.002(3) N4 0.042(5) 0.038(4) 0.042(4) -0.002(4) 0.010(4) -0.008(4) N5 0.032(4) 0.036(4) 0.050(5) 0.004(4) 0.006(4) 0.006(3) N6 0.039(4) 0.050(5) 0.037(4) 0.001(3) 0.014(3) -0.003(4) O1 0.108(7) 0.048(4) 0.044(4) 0.001(3) 0.020(4) 0.002(4) O2 0.052(4) 0.042(4) 0.069(5) -0.005(4) 0.011(4) -0.010(3) O3 0.039(4) 0.079(6) 0.095(6) 0.003(5) 0.011(4) 0.002(4) O4 0.061(4) 0.073(5) 0.058(5) -0.028(4) 0.021(4) -0.005(4) O5 0.083(6) 0.118(8) 0.081(7) -0.040(6) 0.000(5) -0.031(6) O6 0.080(7) 0.128(9) 0.120(9) -0.028(7) 0.029(6) 0.046(6) O7 0.044(4) 0.040(4) 0.053(4) 0.008(3) 0.006(3) -0.003(3) O8 0.035(4) 0.053(4) 0.058(4) 0.003(3) 0.003(3) 0.001(3) Pb1 0.0411(2) 0.0364(2) 0.0436(2) 0.00277(18) 0.01804(14) 0.00055(18) S1 0.0418(12) 0.0454(14) 0.0420(13) 0.0003(11) 0.0120(10) 0.0003(11) S2 0.0646(19) 0.089(2) 0.0593(19) -0.0240(17) 0.0224(15) -0.0149(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.353(11) . ? C1 C2 1.389(13) . ? C1 C20 1.452(13) . ? C2 C3 1.372(15) . ? C2 H2 0.9500 . ? C3 C4 1.343(14) . ? C3 H3 0.9500 . ? C4 C5 1.409(13) . ? C4 H4 0.9500 . ? C5 N1 1.325(11) . ? C5 N2 1.412(11) . ? C6 N2 1.486(13) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N3 1.290(11) . ? C7 C8 1.443(13) . ? C7 H7 0.9500 . ? C8 N4 1.336(12) . ? C8 C9 1.409(12) . ? C9 C10 1.378(15) . ? C9 H9 0.9500 . ? C10 C11 1.347(14) . ? C10 H10 0.9500 . ? C11 C12 1.391(12) . ? C11 H11 0.9500 . ? C12 N4 1.360(12) . ? C12 C13 1.471(14) . ? C13 N5 1.257(11) . ? C13 H13 0.9500 . ? C14 N5 1.461(12) . ? C14 C15 1.518(14) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O7 1.426(11) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O7 1.413(12) . ? C16 C17 1.515(14) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O8 1.432(12) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O8 1.425(11) . ? C18 C19 1.485(13) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N6 1.457(11) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N6 1.290(12) . ? C20 H20 0.9500 . ? C21 F3 1.317(12) . ? C21 F1 1.320(13) . ? C21 F2 1.325(12) . ? C21 S1 1.816(11) . ? C22 F4 1.28(2) . ? C22 F6 1.32(2) . ? C22 F5 1.327(18) . ? C22 S2 1.81(2) . ? N1 Pb1 2.757(7) . ? N2 N3 1.341(10) . ? N3 Pb1 2.713(7) . ? N4 Pb1 2.620(7) . ? N5 Pb1 2.676(7) . ? O1 S1 1.444(7) . ? O1 Pb1 2.542(8) . ? O2 S1 1.435(7) . ? O3 S1 1.423(8) . ? O4 S2 1.437(7) . ? O4 Pb1 2.558(8) . ? O5 S2 1.388(9) . ? O6 S2 1.452(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.0(9) . . ? N1 C1 C20 120.5(8) . . ? C2 C1 C20 117.5(9) . . ? C3 C2 C1 118.6(9) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 120.1(10) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.9(10) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 122.1(8) . . ? N1 C5 N2 117.4(8) . . ? C4 C5 N2 120.4(9) . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 119.8(8) . . ? N3 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? N4 C8 C9 121.5(9) . . ? N4 C8 C7 119.1(8) . . ? C9 C8 C7 119.4(9) . . ? C10 C9 C8 118.9(10) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C11 C10 C9 120.1(9) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.0(8) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? N4 C12 C11 122.4(9) . . ? N4 C12 C13 115.6(8) . . ? C11 C12 C13 122.0(8) . . ? N5 C13 C12 121.2(9) . . ? N5 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? N5 C14 C15 108.1(8) . . ? N5 C14 H14A 110.1 . . ? C15 C14 H14A 110.1 . . ? N5 C14 H14B 110.1 . . ? C15 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? O7 C15 C14 108.1(8) . . ? O7 C15 H15A 110.1 . . ? C14 C15 H15A 110.1 . . ? O7 C15 H15B 110.1 . . ? C14 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? O7 C16 C17 110.9(9) . . ? O7 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? O7 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? O8 C17 C16 111.1(9) . . ? O8 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? O8 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? O8 C18 C19 109.5(8) . . ? O8 C18 H18A 109.8 . . ? C19 C18 H18A 109.8 . . ? O8 C18 H18B 109.8 . . ? C19 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? N6 C19 C18 111.7(8) . . ? N6 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? N6 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? N6 C20 C1 122.5(8) . . ? N6 C20 H20 118.7 . . ? C1 C20 H20 118.7 . . ? F3 C21 F1 109.3(10) . . ? F3 C21 F2 106.9(9) . . ? F1 C21 F2 107.1(9) . . ? F3 C21 S1 110.8(8) . . ? F1 C21 S1 111.2(8) . . ? F2 C21 S1 111.3(8) . . ? F4 C22 F6 110(2) . . ? F4 C22 F5 107.5(15) . . ? F6 C22 F5 104.3(17) . . ? F4 C22 S2 111.1(15) . . ? F6 C22 S2 109.0(12) . . ? F5 C22 S2 114.4(15) . . ? C5 N1 C1 118.1(8) . . ? C5 N1 Pb1 121.7(6) . . ? C1 N1 Pb1 120.2(6) . . ? N3 N2 C5 118.3(7) . . ? N3 N2 C6 119.2(8) . . ? C5 N2 C6 122.6(8) . . ? C7 N3 N2 119.3(8) . . ? C7 N3 Pb1 118.4(6) . . ? N2 N3 Pb1 121.1(5) . . ? C8 N4 C12 118.1(8) . . ? C8 N4 Pb1 120.5(6) . . ? C12 N4 Pb1 121.3(6) . . ? C13 N5 C14 119.2(8) . . ? C13 N5 Pb1 120.0(6) . . ? C14 N5 Pb1 120.8(6) . . ? C20 N6 C19 117.3(7) . . ? S1 O1 Pb1 117.3(4) . . ? S2 O4 Pb1 131.6(5) . . ? C16 O7 C15 112.5(8) . . ? C18 O8 C17 113.3(7) . . ? O1 Pb1 O4 150.7(2) . . ? O1 Pb1 N4 72.7(2) . . ? O4 Pb1 N4 83.5(2) . . ? O1 Pb1 N5 79.9(2) . . ? O4 Pb1 N5 103.9(2) . . ? N4 Pb1 N5 61.6(2) . . ? O1 Pb1 N3 84.9(2) . . ? O4 Pb1 N3 68.5(2) . . ? N4 Pb1 N3 61.8(2) . . ? N5 Pb1 N3 123.4(2) . . ? O1 Pb1 N1 95.7(2) . . ? O4 Pb1 N1 81.3(2) . . ? N4 Pb1 N1 119.9(2) . . ? N5 Pb1 N1 174.8(2) . . ? N3 Pb1 N1 58.5(2) . . ? O3 S1 O2 116.2(5) . . ? O3 S1 O1 114.4(5) . . ? O2 S1 O1 113.8(5) . . ? O3 S1 C21 103.7(5) . . ? O2 S1 C21 104.4(5) . . ? O1 S1 C21 102.0(5) . . ? O5 S2 O4 116.1(5) . . ? O5 S2 O6 113.7(7) . . ? O4 S2 O6 115.9(6) . . ? O5 S2 C22 105.8(8) . . ? O4 S2 C22 99.8(7) . . ? O6 S2 C22 102.8(9) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 3.390 _refine_diff_density_min -2.261 _refine_diff_density_rms 0.158 data_su25 _database_code_depnum_ccdc_archive 'CCDC 703875' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 F6 N4 O8 Pb S2' _chemical_formula_weight 773.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 9.5365(19) _cell_length_b 12.446(3) _cell_length_c 10.605(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.52(3) _cell_angle_gamma 90.00 _cell_volume 1178.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10711 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 7.431 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0754 _exptl_absorpt_correction_T_max 0.1640 _exptl_absorpt_process_details wingx _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method 'phi&omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12942 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2709 _reflns_number_gt 2281 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.4477P] 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 2709 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 -0.0719(10) 0.7604(6) 0.1651(8) 0.0616(18) Uani 1 1 d . . . C2 C -0.0435(8) 0.3793(6) 0.3653(7) 0.0472(15) Uani 1 1 d . . . H2 H -0.0398 0.4555 0.3615 0.057 Uiso 1 1 calc R . . C3 C -0.1432(8) 0.3327(6) 0.4165(6) 0.0497(15) Uani 1 1 d . . . H3 H -0.2081 0.3754 0.4464 0.060 Uiso 1 1 calc R . . C4 C -0.1459(7) 0.2222(6) 0.4232(6) 0.0472(14) Uani 1 1 d . . . C5 C -0.2500(10) 0.1664(9) 0.4806(9) 0.072(2) Uani 1 1 d . . . H5 H -0.3139 0.2095 0.5111 0.087 Uiso 1 1 calc R . . C6 C -0.0518(7) 0.1616(6) 0.3779(6) 0.0460(14) Uani 1 1 d . A . H6 H -0.0534 0.0854 0.3815 0.055 Uiso 1 1 calc R . . C7 C 0.0450(6) 0.2143(5) 0.3270(6) 0.0410(13) Uani 1 1 d . . . F1 F 0.0554(8) 0.8109(5) 0.1843(8) 0.120(3) Uani 1 1 d . . . F2 F -0.0892(6) 0.7599(4) 0.2822(5) 0.0820(15) Uani 1 1 d . . . F3 F -0.1873(8) 0.8158(5) 0.0833(6) 0.108(2) Uani 1 1 d . . . N1 N 0.0482(6) 0.3221(4) 0.3206(5) 0.0409(11) Uani 1 1 d . A . N2 N 0.2500 0.2078(6) 0.2500 0.0405(15) Uani 1 2 d S . . C8 C 0.1452(7) 0.1561(5) 0.2795(7) 0.0530(16) Uani 0.50 1 d P A 1 H8 H 0.1364 0.0804 0.2692 0.079 Uiso 0.50 1 calc PR A 1 N3 N 0.1452(7) 0.1561(5) 0.2795(7) 0.0530(16) Uani 0.50 1 d P A 2 C9 C 0.1149(17) 0.0382(10) 0.2359(17) 0.053(3) Uani 0.50 1 d P A 2 H9A H 0.0874 0.0330 0.1380 0.080 Uiso 0.50 1 calc PR A 2 H9B H 0.0328 0.0107 0.2621 0.080 Uiso 0.50 1 calc PR A 2 H9C H 0.2053 -0.0045 0.2799 0.080 Uiso 0.50 1 calc PR A 2 O1 O 0.0519(8) 0.5789(4) 0.2071(7) 0.0746(19) Uani 1 1 d . . . O2 O -0.2091(9) 0.5813(4) 0.0824(9) 0.083(2) Uani 1 1 d . . . O3 O -0.0425(8) 0.6460(5) -0.0230(6) 0.0822(19) Uani 1 1 d . . . O4 O -0.2570(11) 0.0711(6) 0.4900(10) 0.099(3) Uani 1 1 d . . . Pb1 Pb 0.2500 0.41390(2) 0.2500 0.04113(14) Uani 1 2 d S . . S1 S -0.0642(2) 0.62605(13) 0.10101(16) 0.0471(4) Uani 1 1 d . A . 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 0.082(5) 0.048(4) 0.053(4) -0.005(3) 0.022(4) 0.002(4) C2 0.057(4) 0.040(3) 0.045(4) -0.001(3) 0.019(3) 0.004(3) C3 0.059(4) 0.054(4) 0.035(3) -0.002(3) 0.016(3) 0.007(3) C4 0.045(3) 0.060(4) 0.038(3) 0.000(3) 0.017(3) 0.000(3) C5 0.073(5) 0.096(7) 0.064(5) 0.006(5) 0.046(4) 0.009(5) C6 0.047(3) 0.048(4) 0.046(3) 0.002(3) 0.020(3) -0.006(3) C7 0.037(3) 0.042(3) 0.045(3) 0.001(3) 0.016(3) -0.002(2) F1 0.148(6) 0.077(4) 0.181(7) -0.068(4) 0.116(6) -0.056(4) F2 0.077(3) 0.110(4) 0.065(3) -0.025(3) 0.032(2) 0.014(3) F3 0.154(6) 0.072(4) 0.079(4) 0.001(3) 0.019(4) 0.054(4) N1 0.047(3) 0.034(3) 0.040(3) -0.002(2) 0.014(2) 0.002(2) N2 0.039(4) 0.034(4) 0.053(4) 0.000 0.022(3) 0.000 C8 0.062(4) 0.027(3) 0.088(5) 0.001(3) 0.049(4) 0.001(2) N3 0.062(4) 0.027(3) 0.088(5) 0.001(3) 0.049(4) 0.001(2) C9 0.067(9) 0.022(6) 0.079(10) -0.008(6) 0.036(8) 0.002(6) O1 0.082(4) 0.059(4) 0.065(4) -0.003(2) 0.003(3) 0.030(3) O2 0.065(4) 0.071(5) 0.100(5) -0.009(3) 0.012(4) -0.009(3) O3 0.139(6) 0.059(4) 0.070(4) -0.010(3) 0.063(4) -0.001(4) O4 0.128(7) 0.076(5) 0.132(7) 0.002(4) 0.095(6) -0.023(4) Pb1 0.0417(2) 0.02547(19) 0.0571(2) 0.000 0.01846(16) 0.000 S1 0.0607(10) 0.0318(8) 0.0428(8) 0.0009(6) 0.0107(7) 0.0042(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 F2 1.309(9) . ? C1 F1 1.319(10) . ? C1 F3 1.330(10) . ? C1 S1 1.816(7) . ? C2 N1 1.336(8) . ? C2 C3 1.378(10) . ? C2 H2 0.9500 . ? C3 C4 1.378(10) . ? C3 H3 0.9500 . ? C4 C6 1.381(9) . ? C4 C5 1.503(10) . ? C5 O4 1.195(11) . ? C5 H5 0.9500 . ? C6 C7 1.387(8) . ? C6 H6 0.9500 . ? C7 N1 1.344(8) . ? C7 C8 1.424(8) . ? N1 Pb1 2.565(5) . ? N2 C8 1.315(6) . ? N2 N3 1.315(6) 2 ? N2 C8 1.315(6) 2 ? N2 Pb1 2.565(7) . ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O1 S1 1.401(6) . ? O1 Pb1 2.718(5) . ? O2 S1 1.438(8) . ? O3 S1 1.423(6) . ? O3 Pb1 2.632(7) 3_565 ? Pb1 N1 2.565(5) 2 ? Pb1 O3 2.632(7) 3_565 ? Pb1 O3 2.632(7) 4_666 ? Pb1 O1 2.718(5) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 C1 F1 105.7(7) . . ? F2 C1 F3 105.7(7) . . ? F1 C1 F3 111.1(7) . . ? F2 C1 S1 112.7(6) . . ? F1 C1 S1 110.0(6) . . ? F3 C1 S1 111.5(6) . . ? N1 C2 C3 122.9(6) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 118.0(6) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C6 120.0(6) . . ? C3 C4 C5 120.6(7) . . ? C6 C4 C5 119.4(7) . . ? O4 C5 C4 123.8(8) . . ? O4 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C4 C6 C7 118.7(6) . . ? C4 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? N1 C7 C6 121.4(6) . . ? N1 C7 C8 117.4(5) . . ? C6 C7 C8 121.2(6) . . ? C2 N1 C7 119.0(5) . . ? C2 N1 Pb1 121.1(4) . . ? C7 N1 Pb1 119.5(4) . . ? C8 N2 N3 121.4(7) . 2 ? C8 N2 C8 121.4(7) . 2 ? N3 N2 C8 0.0(7) 2 2 ? C8 N2 Pb1 119.3(4) . . ? N3 N2 Pb1 119.3(4) 2 . ? C8 N2 Pb1 119.3(4) 2 . ? N2 C8 C7 119.7(5) . . ? N2 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? S1 O1 Pb1 139.3(4) . . ? S1 O3 Pb1 119.3(4) . 3_565 ? N2 Pb1 N1 63.55(11) . . ? N2 Pb1 N1 63.55(11) . 2 ? N1 Pb1 N1 127.1(2) . 2 ? N2 Pb1 O3 73.55(14) . 3_565 ? N1 Pb1 O3 74.95(17) . 3_565 ? N1 Pb1 O3 90.43(18) 2 3_565 ? N2 Pb1 O3 73.55(14) . 4_666 ? N1 Pb1 O3 90.43(18) . 4_666 ? N1 Pb1 O3 74.95(17) 2 4_666 ? O3 Pb1 O3 147.1(3) 3_565 4_666 ? N2 Pb1 O1 139.07(15) . . ? N1 Pb1 O1 80.6(2) . . ? N1 Pb1 O1 146.7(2) 2 . ? O3 Pb1 O1 78.8(2) 3_565 . ? O3 Pb1 O1 128.50(19) 4_666 . ? N2 Pb1 O1 139.07(15) . 2 ? N1 Pb1 O1 146.7(2) . 2 ? N1 Pb1 O1 80.6(2) 2 2 ? O3 Pb1 O1 128.50(19) 3_565 2 ? O3 Pb1 O1 78.8(2) 4_666 2 ? O1 Pb1 O1 81.9(3) . 2 ? O1 S1 O3 119.0(5) . . ? O1 S1 O2 113.5(4) . . ? O3 S1 O2 112.6(5) . . ? O1 S1 C1 102.1(3) . . ? O3 S1 C1 102.9(4) . . ? O2 S1 C1 104.2(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.042 _refine_diff_density_min -2.450 _refine_diff_density_rms 0.182 data_lehn24 _database_code_depnum_ccdc_archive 'CCDC 703876' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 F6 N4 O8 S2 Zn' _chemical_formula_weight 631.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 11.6632(15) _cell_length_b 22.296(4) _cell_length_c 8.5280(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.860(8) _cell_angle_gamma 90.00 _cell_volume 2212.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10495 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 1.403 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method '/p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6648 _diffrn_reflns_av_R_equivalents 0.1025 _diffrn_reflns_av_sigmaI/netI 0.1287 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2511 _reflns_number_gt 1541 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0003P)^2^+21.1221P] 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 2511 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1943 _refine_ls_R_factor_gt 0.1171 _refine_ls_wR_factor_ref 0.1697 _refine_ls_wR_factor_gt 0.1503 _refine_ls_goodness_of_fit_ref 1.223 _refine_ls_restrained_S_all 1.223 _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 1.1004(7) 0.0522(4) 0.4901(11) 0.058(3) Uani 1 1 d . A . H1 H 1.1245 0.0211 0.4236 0.070 Uiso 1 1 calc R . . C2 C 1.1080(6) 0.1152(4) 0.4382(8) 0.046(2) Uani 1 1 d . . . C3 C 1.1510(7) 0.1320(5) 0.2982(9) 0.060(3) Uani 1 1 d . . . H3 H 1.1753 0.1030 0.2259 0.072 Uiso 1 1 calc R . . C4 C 1.1573(7) 0.1927(6) 0.2669(10) 0.065(3) Uani 1 1 d . . . H4 H 1.1867 0.2061 0.1716 0.078 Uiso 1 1 calc R . . C5 C 1.1217(7) 0.2333(4) 0.3718(9) 0.053(2) Uani 1 1 d . A . H5 H 1.1262 0.2751 0.3510 0.064 Uiso 1 1 calc R . . C6 C 1.0781(7) 0.2126(4) 0.5117(9) 0.041(2) Uani 1 1 d . . . C9 C 0.6385(8) 0.0627(4) 0.5611(11) 0.053(2) Uani 1 1 d . . . N1 N 1.0705(5) 0.1546(3) 0.5428(7) 0.0363(15) Uani 1 1 d . A . N2 N 1.0000 0.2249(4) 0.7500 0.036(2) Uani 1 2 d S . . O1 O 1.0640(5) 0.0391(2) 0.6166(7) 0.0570(17) Uani 1 1 d . . . O2 O 0.8410(4) 0.1078(2) 0.6158(6) 0.0459(15) Uani 1 1 d . . . O3 O 0.6988(4) 0.1259(3) 0.8062(6) 0.0568(16) Uani 1 1 d . . . O4 O 0.6833(6) 0.1763(3) 0.5521(7) 0.0687(18) Uani 1 1 d . . . F1 F 0.6563(5) 0.0561(3) 0.4101(6) 0.0753(17) Uani 1 1 d . . . F2 F 0.6672(5) 0.0126(2) 0.6349(7) 0.0848(18) Uani 1 1 d . . . F3 F 0.5287(4) 0.0717(3) 0.5737(7) 0.0786(18) Uani 1 1 d . . . S1 S 0.72339(17) 0.12610(11) 0.6443(2) 0.0464(6) Uani 1 1 d . A . Zn1 Zn 1.0000 0.12249(6) 0.7500 0.0344(4) Uani 1 2 d S . . N3 N 1.0403(6) 0.2514(3) 0.6300(8) 0.0425(18) Uani 0.50 1 d P A 1 C8 C 1.0546(16) 0.3179(7) 0.636(2) 0.065(5) Uani 0.50 1 d P A 1 H8A H 0.9789 0.3371 0.6350 0.097 Uiso 0.50 1 calc PR A 1 H8B H 1.0941 0.3313 0.5442 0.097 Uiso 0.50 1 calc PR A 1 H8C H 1.1002 0.3291 0.7321 0.097 Uiso 0.50 1 calc PR A 1 C7 C 1.0403(6) 0.2514(3) 0.6300(8) 0.0425(18) Uani 0.50 1 d P A 2 H7 H 1.0442 0.2938 0.6218 0.051 Uiso 0.50 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 C1 0.054(6) 0.061(6) 0.063(6) -0.022(5) 0.030(5) -0.009(5) C2 0.035(4) 0.069(6) 0.033(4) -0.009(4) 0.005(3) -0.011(4) C3 0.044(5) 0.105(8) 0.032(4) -0.010(6) 0.013(4) -0.004(6) C4 0.043(6) 0.116(9) 0.039(5) 0.009(6) 0.014(4) -0.019(6) C5 0.047(5) 0.074(7) 0.039(5) 0.026(5) 0.005(4) -0.012(5) C6 0.035(4) 0.057(6) 0.030(4) 0.006(4) 0.001(3) -0.006(4) C9 0.050(6) 0.059(6) 0.050(5) -0.010(5) 0.011(4) -0.008(5) N1 0.028(3) 0.053(4) 0.029(3) -0.004(3) 0.007(3) -0.002(3) N2 0.037(5) 0.044(6) 0.026(5) 0.000 0.003(4) 0.000 O1 0.063(4) 0.051(4) 0.061(4) -0.008(3) 0.033(3) -0.008(3) O2 0.039(3) 0.062(4) 0.039(3) -0.009(3) 0.014(2) -0.008(3) O3 0.042(3) 0.087(5) 0.043(3) -0.014(3) 0.012(3) 0.003(4) O4 0.083(5) 0.057(4) 0.066(4) 0.006(4) 0.011(4) 0.000(4) F1 0.080(4) 0.094(4) 0.054(3) -0.026(3) 0.015(3) -0.025(3) F2 0.089(4) 0.056(4) 0.110(5) 0.019(3) 0.013(4) -0.016(3) F3 0.037(3) 0.097(5) 0.102(4) -0.028(4) 0.010(3) -0.016(3) S1 0.0430(13) 0.0553(14) 0.0418(12) -0.0081(12) 0.0091(10) -0.0057(12) Zn1 0.0374(7) 0.0368(8) 0.0307(7) 0.000 0.0152(5) 0.000 N3 0.047(5) 0.039(4) 0.041(4) 0.008(4) 0.004(4) 0.000(4) C8 0.059(12) 0.050(12) 0.085(14) 0.035(11) 0.003(10) -0.007(10) C7 0.047(5) 0.039(4) 0.041(4) 0.008(4) 0.004(4) 0.000(4) _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 O1 1.221(9) . ? C1 C2 1.477(12) . ? C1 H1 0.9500 . ? C2 N1 1.347(9) . ? C2 C3 1.378(10) . ? C3 C4 1.383(13) . ? C3 H3 0.9500 . ? C4 C5 1.357(12) . ? C4 H4 0.9500 . ? C5 C6 1.407(10) . ? C5 H5 0.9500 . ? C6 N1 1.323(10) . ? C6 N3 1.422(10) . ? C9 F3 1.308(9) . ? C9 F2 1.315(10) . ? C9 F1 1.326(9) . ? C9 S1 1.841(9) . ? N1 Zn1 2.123(6) . ? N2 N3 1.297(7) . ? N2 C7 1.297(7) 2_756 ? N2 N3 1.297(7) 2_756 ? N2 Zn1 2.282(9) . ? O1 Zn1 2.329(6) . ? O2 S1 1.467(5) . ? O2 Zn1 2.138(5) . ? O3 S1 1.429(5) . ? O4 S1 1.428(6) . ? Zn1 N1 2.123(6) 2_756 ? Zn1 O2 2.138(5) 2_756 ? Zn1 O1 2.329(6) 2_756 ? N3 C8 1.493(17) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 121.5(8) . . ? O1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? N1 C2 C3 123.3(9) . . ? N1 C2 C1 113.2(7) . . ? C3 C2 C1 123.4(8) . . ? C2 C3 C4 117.5(9) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? C5 C4 C3 120.2(8) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.0(9) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? N1 C6 C5 121.6(8) . . ? N1 C6 N3 115.1(7) . . ? C5 C6 N3 123.3(8) . . ? F3 C9 F2 108.1(8) . . ? F3 C9 F1 108.4(8) . . ? F2 C9 F1 108.6(8) . . ? F3 C9 S1 110.7(6) . . ? F2 C9 S1 110.8(6) . . ? F1 C9 S1 110.2(6) . . ? C6 N1 C2 118.4(7) . . ? C6 N1 Zn1 122.1(5) . . ? C2 N1 Zn1 119.5(5) . . ? N3 N2 C7 125.7(10) . 2_756 ? N3 N2 N3 125.7(10) . 2_756 ? C7 N2 N3 0.0(8) 2_756 2_756 ? N3 N2 Zn1 117.2(5) . . ? C7 N2 Zn1 117.2(5) 2_756 . ? N3 N2 Zn1 117.2(5) 2_756 . ? C1 O1 Zn1 112.5(6) . . ? S1 O2 Zn1 131.0(3) . . ? O4 S1 O3 117.1(4) . . ? O4 S1 O2 113.7(4) . . ? O3 S1 O2 114.2(3) . . ? O4 S1 C9 104.0(4) . . ? O3 S1 C9 103.5(4) . . ? O2 S1 C9 101.9(4) . . ? N1 Zn1 N1 140.5(4) 2_756 . ? N1 Zn1 O2 88.7(2) 2_756 2_756 ? N1 Zn1 O2 97.3(2) . 2_756 ? N1 Zn1 O2 97.3(2) 2_756 . ? N1 Zn1 O2 88.7(2) . . ? O2 Zn1 O2 162.4(3) 2_756 . ? N1 Zn1 N2 70.27(18) 2_756 . ? N1 Zn1 N2 70.27(18) . . ? O2 Zn1 N2 98.81(15) 2_756 . ? O2 Zn1 N2 98.81(15) . . ? N1 Zn1 O1 146.2(2) 2_756 . ? N1 Zn1 O1 73.0(2) . . ? O2 Zn1 O1 81.0(2) 2_756 . ? O2 Zn1 O1 84.9(2) . . ? N2 Zn1 O1 142.98(14) . . ? N1 Zn1 O1 73.0(2) 2_756 2_756 ? N1 Zn1 O1 146.2(2) . 2_756 ? O2 Zn1 O1 84.9(2) 2_756 2_756 ? O2 Zn1 O1 81.0(2) . 2_756 ? N2 Zn1 O1 142.98(14) . 2_756 ? O1 Zn1 O1 74.0(3) . 2_756 ? N2 N3 C6 115.4(7) . . ? N2 N3 C8 118.2(10) . . ? C6 N3 C8 126.1(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 -0.4(12) . . . . ? O1 C1 C2 C3 178.5(8) . . . . ? N1 C2 C3 C4 1.3(13) . . . . ? C1 C2 C3 C4 -177.5(8) . . . . ? C2 C3 C4 C5 -0.2(13) . . . . ? C3 C4 C5 C6 -0.3(13) . . . . ? C4 C5 C6 N1 -0.3(12) . . . . ? C4 C5 C6 N3 179.0(8) . . . . ? C5 C6 N1 C2 1.3(11) . . . . ? N3 C6 N1 C2 -178.0(6) . . . . ? C5 C6 N1 Zn1 -178.0(6) . . . . ? N3 C6 N1 Zn1 2.6(9) . . . . ? C3 C2 N1 C6 -1.8(11) . . . . ? C1 C2 N1 C6 177.0(7) . . . . ? C3 C2 N1 Zn1 177.5(6) . . . . ? C1 C2 N1 Zn1 -3.6(9) . . . . ? C2 C1 O1 Zn1 3.6(11) . . . . ? Zn1 O2 S1 O4 102.7(5) . . . . ? Zn1 O2 S1 O3 -35.2(6) . . . . ? Zn1 O2 S1 C9 -146.1(5) . . . . ? F3 C9 S1 O4 -60.5(7) . . . . ? F2 C9 S1 O4 179.6(6) . . . . ? F1 C9 S1 O4 59.4(7) . . . . ? F3 C9 S1 O3 62.3(7) . . . . ? F2 C9 S1 O3 -57.6(7) . . . . ? F1 C9 S1 O3 -177.8(6) . . . . ? F3 C9 S1 O2 -178.9(6) . . . . ? F2 C9 S1 O2 61.2(7) . . . . ? F1 C9 S1 O2 -59.0(7) . . . . ? C6 N1 Zn1 N1 -1.6(5) . . . 2_756 ? C2 N1 Zn1 N1 179.1(6) . . . 2_756 ? C6 N1 Zn1 O2 -98.4(6) . . . 2_756 ? C2 N1 Zn1 O2 82.3(6) . . . 2_756 ? C6 N1 Zn1 O2 98.3(6) . . . . ? C2 N1 Zn1 O2 -81.1(5) . . . . ? C6 N1 Zn1 N2 -1.6(5) . . . . ? C2 N1 Zn1 N2 179.1(6) . . . . ? C6 N1 Zn1 O1 -176.7(6) . . . . ? C2 N1 Zn1 O1 4.0(5) . . . . ? C6 N1 Zn1 O1 169.9(5) . . . 2_756 ? C2 N1 Zn1 O1 -9.4(8) . . . 2_756 ? S1 O2 Zn1 N1 11.5(5) . . . 2_756 ? S1 O2 Zn1 N1 -129.3(5) . . . . ? S1 O2 Zn1 O2 120.5(4) . . . 2_756 ? S1 O2 Zn1 N2 -59.5(4) . . . . ? S1 O2 Zn1 O1 157.6(4) . . . . ? S1 O2 Zn1 O1 83.0(4) . . . 2_756 ? N3 N2 Zn1 N1 -179.7(4) . . . 2_756 ? C7 N2 Zn1 N1 0.3(4) 2_756 . . 2_756 ? N3 N2 Zn1 N1 0.3(4) 2_756 . . 2_756 ? N3 N2 Zn1 N1 0.3(4) . . . . ? C7 N2 Zn1 N1 -179.7(4) 2_756 . . . ? N3 N2 Zn1 N1 -179.7(4) 2_756 . . . ? N3 N2 Zn1 O2 94.9(4) . . . 2_756 ? C7 N2 Zn1 O2 -85.1(4) 2_756 . . 2_756 ? N3 N2 Zn1 O2 -85.1(4) 2_756 . . 2_756 ? N3 N2 Zn1 O2 -85.1(4) . . . . ? C7 N2 Zn1 O2 94.9(4) 2_756 . . . ? N3 N2 Zn1 O2 94.9(4) 2_756 . . . ? N3 N2 Zn1 O1 8.1(4) . . . . ? C7 N2 Zn1 O1 -171.9(4) 2_756 . . . ? N3 N2 Zn1 O1 -171.9(4) 2_756 . . . ? N3 N2 Zn1 O1 -171.9(4) . . . 2_756 ? C7 N2 Zn1 O1 8.1(4) 2_756 . . 2_756 ? N3 N2 Zn1 O1 8.1(4) 2_756 . . 2_756 ? C1 O1 Zn1 N1 -178.4(6) . . . 2_756 ? C1 O1 Zn1 N1 -4.0(6) . . . . ? C1 O1 Zn1 O2 -104.5(6) . . . 2_756 ? C1 O1 Zn1 O2 86.2(6) . . . . ? C1 O1 Zn1 N2 -11.7(7) . . . . ? C1 O1 Zn1 O1 168.3(7) . . . 2_756 ? C7 N2 N3 C6 -179.1(7) 2_756 . . . ? N3 N2 N3 C6 -179.1(7) 2_756 . . . ? Zn1 N2 N3 C6 0.9(7) . . . . ? C7 N2 N3 C8 7.3(9) 2_756 . . . ? N3 N2 N3 C8 7.3(9) 2_756 . . . ? Zn1 N2 N3 C8 -172.7(9) . . . . ? N1 C6 N3 N2 -2.2(10) . . . . ? C5 C6 N3 N2 178.5(6) . . . . ? N1 C6 N3 C8 170.8(11) . . . . ? C5 C6 N3 C8 -8.6(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.601 _refine_diff_density_min -0.743 _refine_diff_density_rms 0.100