# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _publ_section_title ;Dithiazolylethene-based molecular switches for nonlinear optical properties and fluorescence: synthesis, crystal structure and ligating properties ; loop_ _publ_author_name _publ_author_address M.Giraud ;Universit\'e Paris Sud Institut de Chimie Mol\'eculaire et Mat\'eriaux d'Orsay, UMR 8182 Equipe Chimie Inorganique, B\^at. 420, 91405 Orsay (France) ; A.Leaustic ;Universit\'e Paris Sud Institut de Chimie Mol\'eculaire et Mat\'eriaux d'Orsay, UMR 8182 Equipe Chimie Inorganique, B\^at. 420, 91405 Orsay (France) ; R.Guillot ;Universit\'e Paris Sud Institut de Chimie Mol\'eculaire et Mat\'eriaux d'Orsay, UMR 8182 B\^at. 420, 91405 Orsay (France) ; 'Pei Yu.' ;Universit\'e Paris Sud Institut de Chimie Mol\'eculaire et Mat\'eriaux d'Orsay, UMR 8182 B\^at. 420, 91405 Orsay (France) ; P.G.Lacroix ;Laboratoire de Chimie de Coordination du CNRS 205 route de Narbonne, 31077 Toulouse (France) ; K.Nakatani ;PPSM, ENS de Cachan, UMR 8531 61 avenue du Pdt. Wilson, 94235 Cachan (France) ; ; R.Pansu ; ;PPSM, ENS de Cachan, UMR 8531 61 avenue du Pdt. Wilson, 94235 Cachan (France) ; _publ_contact_author_address ;Universit\'e Paris Sud Institut de Chimie Mol\'eculaire et Mat\'eriaux d'Orsay, UMR 8182 Equipe Chimie Inorganique, B\^at. 420, 91405 Orsay (France) ; _publ_contact_author_email yupei@icmo.u-psud.fr _publ_contact_author_fax '(+33) 1 69 15 47 54' _publ_contact_author_name 'Pei Yu' data_Mn(hfac)2.2a _database_code_depnum_ccdc_archive 'CCDC 633201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Mn [1-[5-ethoxy-2-(4-nitrophenyl)thiazoyl]-2-[4-methyl-2-(2-pyridyl)thiazoyl] perfluorocyclopentene] (hfac)2 ; _chemical_name_common ; Mn (1-(5-ethoxy-2-(4-nitrophenyl)thiazoyl)-2-(4-methyl-2-(2- pyridyl)thiazoyl) perfluorocyclopentene) (hfac)2 ; _chemical_melting_point ? _chemical_formula_moiety 'C35 H18 F18 Mn N4 O7 S2' _chemical_formula_sum 'C35 H18 F18 Mn N4 O7 S2' _chemical_formula_weight 1067.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3370 0.7280 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9560(6) _cell_length_b 12.0233(9) _cell_length_c 19.2448(14) _cell_angle_alpha 83.695(2) _cell_angle_beta 87.711(2) _cell_angle_gamma 73.878(2) _cell_volume 1978.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 3674 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 30.37 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1062 _exptl_absorpt_coefficient_mu 0.579 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'X8 APEX II Bruker' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13780 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 32.42 _reflns_number_total 9860 _reflns_number_gt 6581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^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 9860 _refine_ls_number_parameters 604 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.33601(4) 0.32008(3) 0.13803(2) 0.01378(10) Uani 1 1 d . . . S1 S 0.12140(7) 0.67956(5) 0.22181(3) 0.01512(14) Uani 1 1 d . . . S2 S 0.08912(8) 0.33845(6) 0.46742(4) 0.01813(15) Uani 1 1 d . . . F8 F 0.84663(17) -0.00414(14) 0.05298(9) 0.0264(4) Uani 1 1 d . . . F9 F 0.62826(19) -0.04564(14) 0.05165(9) 0.0268(4) Uani 1 1 d . . . F14 F 0.1084(2) -0.05646(14) 0.15704(9) 0.0328(4) Uani 1 1 d . . . F3 F -0.3228(2) 0.83740(14) 0.38023(9) 0.0300(4) Uani 1 1 d . . . F2 F -0.46593(18) 0.61849(15) 0.33090(9) 0.0295(4) Uani 1 1 d . . . F13 F 0.34844(19) -0.06791(13) 0.17176(9) 0.0289(4) Uani 1 1 d . . . F7 F 0.67263(19) 0.09027(14) -0.02115(8) 0.0256(4) Uani 1 1 d . . . O1 O 0.1254(2) 0.53216(16) 0.38989(10) 0.0194(4) Uani 1 1 d . . . O2 O 0.5039(2) 0.20806(16) 0.07496(9) 0.0189(4) Uani 1 1 d . . . O5 O 0.1633(2) 0.33615(15) 0.06051(9) 0.0162(4) Uani 1 1 d . . . F1 F -0.40151(18) 0.65445(14) 0.43176(8) 0.0270(4) Uani 1 1 d . . . O3 O 0.5114(2) 0.26273(16) 0.21677(9) 0.0193(4) Uani 1 1 d . . . F5 F -0.17289(19) 0.84589(14) 0.26480(10) 0.0317(4) Uani 1 1 d . . . F18 F -0.0830(2) 0.40094(15) -0.02446(9) 0.0377(5) Uani 1 1 d . . . F17 F -0.0917(2) 0.22608(15) -0.02501(9) 0.0344(4) Uani 1 1 d . . . F12 F 0.7346(2) 0.24854(15) 0.30841(9) 0.0315(4) Uani 1 1 d . . . N1 N 0.4435(2) 0.46925(18) 0.11203(11) 0.0149(5) Uani 1 1 d . . . F6 F -0.31997(19) 0.76903(16) 0.21045(8) 0.0321(4) Uani 1 1 d . . . F15 F 0.1828(2) -0.00934(14) 0.25161(8) 0.0313(4) Uani 1 1 d . . . F4 F -0.51085(19) 0.84354(15) 0.31139(9) 0.0324(4) Uani 1 1 d . . . O4 O 0.2566(2) 0.17477(15) 0.18108(9) 0.0185(4) Uani 1 1 d . . . C17 C 0.2322(3) 0.5654(2) 0.18076(13) 0.0128(5) Uani 1 1 d . . . N2 N 0.1813(2) 0.47218(17) 0.18848(11) 0.0128(4) Uani 1 1 d . . . F16 F 0.0980(2) 0.27923(18) -0.07396(8) 0.0355(5) Uani 1 1 d . . . C7 C 0.1838(3) 0.1207(2) 0.14947(13) 0.0142(5) Uani 1 1 d . . . C20 C -0.0037(3) 0.5974(2) 0.25056(13) 0.0135(5) Uani 1 1 d . . . N3 N -0.1928(2) 0.40749(18) 0.42299(11) 0.0154(5) Uani 1 1 d . . . C369 C -0.2769(3) 0.2000(2) 0.48344(15) 0.0217(6) Uani 1 1 d . . . H369 H -0.3432 0.2493 0.4502 0.026 Uiso 1 1 calc R . . C26 C -0.1178(3) 0.4860(2) 0.39179(13) 0.0140(5) Uani 1 1 d . . . F11 F 0.6539(3) 0.09933(19) 0.33230(10) 0.0546(6) Uani 1 1 d . . . C27 C 0.0355(3) 0.4627(2) 0.41027(13) 0.0154(5) Uani 1 1 d . . . C9 C 0.0956(3) 0.2613(2) 0.04920(13) 0.0132(5) Uani 1 1 d . . . F10 F 0.8675(2) 0.0863(2) 0.27649(11) 0.0637(7) Uani 1 1 d . . . C19 C -0.0311(3) 0.3939(2) 0.23868(14) 0.0184(6) Uani 1 1 d . . . H19A H 0.0294 0.3277 0.2167 0.028 Uiso 1 1 calc R . . H19B H -0.1330 0.4201 0.2187 0.028 Uiso 1 1 calc R . . H19C H -0.0396 0.3724 0.2879 0.028 Uiso 1 1 calc R . . C5 C 0.6936(3) 0.0426(2) 0.04442(14) 0.0182(6) Uani 1 1 d . . . C12 C 0.5760(3) 0.4634(2) 0.07684(15) 0.0203(6) Uani 1 1 d . . . H12 H 0.6275 0.3941 0.0588 0.024 Uiso 1 1 calc R . . C16 C 0.3732(3) 0.5686(2) 0.13968(13) 0.0140(5) Uani 1 1 d . . . C13 C 0.6403(3) 0.5563(3) 0.06597(15) 0.0229(6) Uani 1 1 d . . . H13 H 0.7337 0.5492 0.0416 0.028 Uiso 1 1 calc R . . C14 C 0.5634(3) 0.6589(2) 0.09187(15) 0.0227(6) Uani 1 1 d . . . H14 H 0.6016 0.7237 0.0835 0.027 Uiso 1 1 calc R . . C21 C -0.1419(3) 0.6439(2) 0.29228(13) 0.0148(5) Uani 1 1 d . . . C18 C 0.0463(3) 0.4893(2) 0.22738(13) 0.0144(5) Uani 1 1 d . . . C10 C 0.2037(3) -0.0040(2) 0.18324(14) 0.0209(6) Uani 1 1 d . . . O7 O -0.1555(3) -0.14124(19) 0.63803(11) 0.0387(6) Uani 1 1 d . . . O6 O -0.3676(3) -0.0968(2) 0.57845(15) 0.0498(7) Uani 1 1 d . . . C8 C 0.0989(3) 0.1572(2) 0.08847(14) 0.0153(5) Uani 1 1 d . . . H8 H 0.0425 0.1102 0.0735 0.018 Uiso 1 1 calc R . . C1 C 0.6211(3) 0.1299(2) 0.09676(14) 0.0153(5) Uani 1 1 d . . . N4 N -0.2497(3) -0.0757(2) 0.59639(14) 0.0308(6) Uani 1 1 d . . . C30 C -0.1006(3) 0.3256(2) 0.46311(13) 0.0159(5) Uani 1 1 d . . . C31 C -0.1412(3) 0.2251(2) 0.50056(13) 0.0163(5) Uani 1 1 d . . . C33 C -0.0814(4) 0.0551(3) 0.58346(15) 0.0274(7) Uani 1 1 d . . . H33 H -0.0164 0.0059 0.6172 0.033 Uiso 1 1 calc R . . C11 C 0.0033(3) 0.2915(2) -0.01865(14) 0.0165(5) Uani 1 1 d . . . C25 C -0.1977(3) 0.5894(2) 0.34813(13) 0.0139(5) Uani 1 1 d . . . C35 C -0.3139(3) 0.1023(2) 0.51553(16) 0.0256(6) Uani 1 1 d . . . H35 H -0.4040 0.0849 0.5038 0.031 Uiso 1 1 calc R . . C28 C 0.2888(3) 0.4944(2) 0.40875(14) 0.0191(6) Uani 1 1 d . . . H28A H 0.2987 0.4578 0.4565 0.023 Uiso 1 1 calc R . . H28B H 0.3290 0.5617 0.4066 0.023 Uiso 1 1 calc R . . C2 C 0.6915(3) 0.1119(2) 0.16144(14) 0.0191(6) Uani 1 1 d . . . H2 H 0.7823 0.0518 0.1692 0.023 Uiso 1 1 calc R . . C22 C -0.2487(3) 0.7626(2) 0.27167(14) 0.0200(6) Uani 1 1 d . . . C15 C 0.4295(3) 0.6649(2) 0.13036(15) 0.0210(6) Uani 1 1 d . . . H15 H 0.3777 0.7328 0.1498 0.025 Uiso 1 1 calc R . . C34 C -0.2155(3) 0.0318(2) 0.56477(15) 0.0229(6) Uani 1 1 d . . . C3 C 0.6312(3) 0.1809(2) 0.21555(14) 0.0176(6) Uani 1 1 d . . . C29 C 0.3834(3) 0.4102(2) 0.36119(15) 0.0247(6) Uani 1 1 d . . . H29A H 0.4902 0.3871 0.3753 0.037 Uiso 1 1 calc R . . H29B H 0.3758 0.4467 0.3140 0.037 Uiso 1 1 calc R . . H29C H 0.3450 0.3428 0.3637 0.037 Uiso 1 1 calc R . . C23 C -0.3690(3) 0.7822(2) 0.33164(15) 0.0216(6) Uani 1 1 d . . . C4 C 0.7224(3) 0.1531(2) 0.28348(15) 0.0247(6) Uani 1 1 d . . . C24 C -0.3616(3) 0.6577(2) 0.36328(14) 0.0182(6) Uani 1 1 d . . . C32 C -0.0453(3) 0.1522(2) 0.55136(15) 0.0236(6) Uani 1 1 d . . . H32 H 0.0445 0.1694 0.5638 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0149(2) 0.01077(18) 0.0159(2) -0.00298(15) 0.00001(16) -0.00324(15) S1 0.0182(3) 0.0104(3) 0.0173(3) -0.0023(2) 0.0053(3) -0.0052(2) S2 0.0165(3) 0.0177(3) 0.0184(4) 0.0020(3) -0.0018(3) -0.0029(3) F8 0.0149(8) 0.0278(9) 0.0356(10) -0.0159(8) -0.0023(7) 0.0006(7) F9 0.0288(9) 0.0183(8) 0.0374(10) -0.0102(7) 0.0003(8) -0.0105(7) F14 0.0425(11) 0.0178(8) 0.0428(11) 0.0082(7) -0.0173(9) -0.0179(8) F3 0.0369(10) 0.0219(9) 0.0297(10) -0.0091(7) 0.0022(8) -0.0031(8) F2 0.0176(8) 0.0385(10) 0.0341(10) 0.0003(8) -0.0026(7) -0.0116(8) F13 0.0317(10) 0.0139(8) 0.0352(10) -0.0022(7) -0.0034(8) 0.0041(7) F7 0.0308(9) 0.0257(9) 0.0178(9) -0.0056(7) 0.0021(7) -0.0027(7) O1 0.0142(9) 0.0191(10) 0.0244(11) 0.0030(8) 0.0008(8) -0.0060(8) O2 0.0185(10) 0.0181(9) 0.0168(10) -0.0032(8) -0.0026(8) 0.0014(7) O5 0.0187(9) 0.0131(9) 0.0177(10) 0.0003(7) -0.0013(8) -0.0061(7) F1 0.0251(9) 0.0298(9) 0.0170(9) 0.0038(7) 0.0086(7) 0.0037(7) O3 0.0206(10) 0.0172(9) 0.0198(10) -0.0045(8) -0.0029(8) -0.0032(8) F5 0.0302(10) 0.0135(8) 0.0479(12) 0.0013(8) 0.0116(9) -0.0034(7) F18 0.0503(12) 0.0189(9) 0.0334(10) -0.0043(7) -0.0215(9) 0.0117(8) F17 0.0368(10) 0.0379(11) 0.0355(11) 0.0122(8) -0.0192(8) -0.0255(9) F12 0.0395(11) 0.0310(10) 0.0285(10) -0.0055(8) -0.0109(8) -0.0149(8) N1 0.0162(11) 0.0131(10) 0.0157(12) -0.0029(9) 0.0038(9) -0.0047(8) F6 0.0287(10) 0.0405(11) 0.0177(9) 0.0063(8) -0.0023(7) 0.0030(8) F15 0.0516(12) 0.0226(9) 0.0182(9) 0.0054(7) 0.0042(8) -0.0110(8) F4 0.0186(9) 0.0343(10) 0.0317(10) 0.0095(8) 0.0026(8) 0.0084(7) O4 0.0248(10) 0.0142(9) 0.0173(10) 0.0004(7) -0.0051(8) -0.0070(8) C17 0.0158(12) 0.0111(11) 0.0113(13) -0.0003(9) 0.0000(10) -0.0038(9) N2 0.0150(11) 0.0124(10) 0.0111(11) -0.0009(8) 0.0004(9) -0.0041(8) F16 0.0285(10) 0.0617(13) 0.0158(9) -0.0050(9) 0.0012(8) -0.0110(9) C7 0.0153(13) 0.0096(11) 0.0161(14) -0.0007(10) 0.0037(10) -0.0017(9) C20 0.0138(12) 0.0129(12) 0.0134(13) 0.0012(10) 0.0003(10) -0.0038(10) N3 0.0162(11) 0.0159(11) 0.0134(12) -0.0014(9) 0.0034(9) -0.0039(9) C369 0.0208(14) 0.0178(13) 0.0236(16) 0.0019(11) 0.0018(12) -0.0023(11) C26 0.0149(13) 0.0162(12) 0.0106(13) -0.0013(10) 0.0031(10) -0.0041(10) F11 0.0934(18) 0.0613(15) 0.0241(11) 0.0164(10) -0.0185(11) -0.0519(14) C27 0.0172(13) 0.0151(12) 0.0135(13) -0.0038(10) 0.0029(11) -0.0034(10) C9 0.0116(12) 0.0131(12) 0.0131(13) -0.0038(10) 0.0017(10) 0.0001(9) F10 0.0457(13) 0.0809(17) 0.0428(13) -0.0293(12) -0.0257(10) 0.0306(12) C19 0.0204(14) 0.0176(13) 0.0205(15) -0.0059(11) 0.0075(11) -0.0099(11) C5 0.0152(13) 0.0181(13) 0.0224(15) -0.0039(11) -0.0021(11) -0.0055(10) C12 0.0191(14) 0.0198(14) 0.0225(16) -0.0056(11) 0.0050(12) -0.0058(11) C16 0.0158(13) 0.0138(12) 0.0122(13) -0.0012(10) 0.0012(10) -0.0041(10) C13 0.0241(15) 0.0256(15) 0.0217(16) -0.0037(12) 0.0065(12) -0.0116(12) C14 0.0281(16) 0.0207(14) 0.0239(16) -0.0024(12) 0.0094(13) -0.0156(12) C21 0.0166(13) 0.0110(11) 0.0163(14) -0.0033(10) 0.0005(11) -0.0025(10) C18 0.0164(13) 0.0143(12) 0.0127(13) 0.0001(10) 0.0019(10) -0.0050(10) C10 0.0275(15) 0.0163(13) 0.0194(15) 0.0001(11) -0.0045(12) -0.0071(11) O7 0.0642(17) 0.0232(12) 0.0276(13) 0.0051(9) -0.0097(12) -0.0118(11) O6 0.0372(14) 0.0363(14) 0.078(2) 0.0094(13) -0.0047(13) -0.0195(12) C8 0.0161(13) 0.0119(11) 0.0191(14) -0.0016(10) -0.0005(11) -0.0057(10) C1 0.0149(13) 0.0130(12) 0.0191(14) -0.0036(10) 0.0022(11) -0.0049(10) N4 0.0387(16) 0.0195(13) 0.0306(16) -0.0001(11) 0.0055(13) -0.0040(12) C30 0.0187(13) 0.0157(12) 0.0132(13) -0.0037(10) 0.0030(11) -0.0041(10) C31 0.0206(14) 0.0159(12) 0.0102(13) -0.0001(10) 0.0039(11) -0.0024(10) C33 0.0373(18) 0.0250(15) 0.0164(15) 0.0058(12) -0.0036(13) -0.0052(13) C11 0.0153(13) 0.0150(12) 0.0182(14) -0.0012(10) -0.0015(11) -0.0026(10) C25 0.0142(13) 0.0141(12) 0.0130(13) -0.0014(10) 0.0001(10) -0.0032(10) C35 0.0223(15) 0.0221(15) 0.0315(18) -0.0007(12) 0.0059(13) -0.0062(12) C28 0.0136(13) 0.0276(15) 0.0170(14) -0.0015(11) 0.0001(11) -0.0078(11) C2 0.0168(13) 0.0159(13) 0.0231(15) -0.0039(11) -0.0072(11) -0.0001(10) C22 0.0204(14) 0.0197(13) 0.0173(15) 0.0030(11) 0.0007(12) -0.0031(11) C15 0.0258(15) 0.0142(13) 0.0244(16) -0.0044(11) 0.0091(12) -0.0082(11) C34 0.0304(16) 0.0157(13) 0.0207(16) -0.0010(11) 0.0078(13) -0.0049(12) C3 0.0198(13) 0.0134(12) 0.0205(15) -0.0005(10) -0.0027(11) -0.0061(10) C29 0.0210(15) 0.0244(15) 0.0261(16) -0.0036(12) 0.0007(12) -0.0016(12) C23 0.0177(14) 0.0206(14) 0.0210(15) 0.0014(11) -0.0005(12) 0.0025(11) C4 0.0285(16) 0.0199(14) 0.0226(16) -0.0021(12) -0.0063(13) -0.0006(12) C24 0.0149(13) 0.0226(14) 0.0155(14) 0.0007(11) 0.0014(11) -0.0037(11) C32 0.0255(15) 0.0246(15) 0.0198(15) 0.0060(12) -0.0043(12) -0.0080(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O4 2.1376(17) . ? Mn1 O3 2.1440(18) . ? Mn1 O5 2.1471(17) . ? Mn1 O2 2.1532(18) . ? Mn1 N2 2.254(2) . ? Mn1 N1 2.262(2) . ? S1 C17 1.706(2) . ? S1 C20 1.727(2) . ? S2 C27 1.719(3) . ? S2 C30 1.755(3) . ? F8 C5 1.339(3) . ? F9 C5 1.339(3) . ? F14 C10 1.335(3) . ? F3 C23 1.344(3) . ? F2 C24 1.356(3) . ? F13 C10 1.335(3) . ? F7 C5 1.325(3) . ? O1 C27 1.333(3) . ? O1 C28 1.455(3) . ? O2 C1 1.250(3) . ? O5 C9 1.258(3) . ? F1 C24 1.351(3) . ? O3 C3 1.239(3) . ? F5 C22 1.350(3) . ? F18 C11 1.323(3) . ? F17 C11 1.326(3) . ? F12 C4 1.325(3) . ? N1 C12 1.331(3) . ? N1 C16 1.342(3) . ? F6 C22 1.347(3) . ? F15 C10 1.318(3) . ? F4 C23 1.329(3) . ? O4 C7 1.254(3) . ? C17 N2 1.315(3) . ? C17 C16 1.470(3) . ? N2 C18 1.374(3) . ? F16 C11 1.329(3) . ? C7 C8 1.386(4) . ? C7 C10 1.533(4) . ? C20 C18 1.369(3) . ? C20 C21 1.457(3) . ? N3 C30 1.296(3) . ? N3 C26 1.378(3) . ? C369 C35 1.383(4) . ? C369 C31 1.390(4) . ? C26 C27 1.376(3) . ? C26 C25 1.445(3) . ? F11 C4 1.310(4) . ? C9 C8 1.383(3) . ? C9 C11 1.528(4) . ? F10 C4 1.335(3) . ? C19 C18 1.490(3) . ? C5 C1 1.529(4) . ? C12 C13 1.385(4) . ? C16 C15 1.378(3) . ? C13 C14 1.372(4) . ? C14 C15 1.373(4) . ? C21 C25 1.349(4) . ? C21 C22 1.503(4) . ? O7 N4 1.233(3) . ? O6 N4 1.223(3) . ? C1 C2 1.386(4) . ? N4 C34 1.472(4) . ? C30 C31 1.464(4) . ? C31 C32 1.386(4) . ? C33 C32 1.373(4) . ? C33 C34 1.376(4) . ? C25 C24 1.505(4) . ? C35 C34 1.367(4) . ? C28 C29 1.498(4) . ? C2 C3 1.400(4) . ? C22 C23 1.538(4) . ? C3 C4 1.525(4) . ? C23 C24 1.537(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 O4 Mn1 O3 85.33(7) . . ? O4 Mn1 O5 83.33(7) . . ? O3 Mn1 O5 166.93(7) . . ? O4 Mn1 O2 89.87(7) . . ? O3 Mn1 O2 84.31(7) . . ? O5 Mn1 O2 89.19(7) . . ? O4 Mn1 N2 104.27(7) . . ? O3 Mn1 N2 98.27(7) . . ? O5 Mn1 N2 90.80(7) . . ? O2 Mn1 N2 165.77(7) . . ? O4 Mn1 N1 169.12(7) . . ? O3 Mn1 N1 84.35(7) . . ? O5 Mn1 N1 107.31(7) . . ? O2 Mn1 N1 92.53(7) . . ? N2 Mn1 N1 73.90(7) . . ? C17 S1 C20 89.60(12) . . ? C27 S2 C30 88.61(12) . . ? C27 O1 C28 118.9(2) . . ? C1 O2 Mn1 126.16(17) . . ? C9 O5 Mn1 127.26(16) . . ? C3 O3 Mn1 126.88(17) . . ? C12 N1 C16 117.9(2) . . ? C12 N1 Mn1 125.50(17) . . ? C16 N1 Mn1 116.36(16) . . ? C7 O4 Mn1 126.49(16) . . ? N2 C17 C16 121.6(2) . . ? N2 C17 S1 114.43(19) . . ? C16 C17 S1 123.93(18) . . ? C17 N2 C18 111.8(2) . . ? C17 N2 Mn1 113.66(17) . . ? C18 N2 Mn1 134.49(16) . . ? O4 C7 C8 128.7(2) . . ? O4 C7 C10 112.5(2) . . ? C8 C7 C10 118.7(2) . . ? C18 C20 C21 128.0(2) . . ? C18 C20 S1 110.16(19) . . ? C21 C20 S1 121.80(18) . . ? C30 N3 C26 111.7(2) . . ? C35 C369 C31 120.4(3) . . ? N3 C26 C27 114.4(2) . . ? N3 C26 C25 122.4(2) . . ? C27 C26 C25 123.0(2) . . ? O1 C27 C26 123.9(2) . . ? O1 C27 S2 125.25(19) . . ? C26 C27 S2 110.71(19) . . ? O5 C9 C8 128.6(2) . . ? O5 C9 C11 113.4(2) . . ? C8 C9 C11 118.0(2) . . ? F7 C5 F8 107.1(2) . . ? F7 C5 F9 107.3(2) . . ? F8 C5 F9 106.9(2) . . ? F7 C5 C1 112.1(2) . . ? F8 C5 C1 113.1(2) . . ? F9 C5 C1 110.0(2) . . ? N1 C12 C13 122.7(2) . . ? N1 C16 C15 122.5(2) . . ? N1 C16 C17 114.3(2) . . ? C15 C16 C17 123.1(2) . . ? C14 C13 C12 118.7(3) . . ? C13 C14 C15 119.2(2) . . ? C25 C21 C20 127.7(2) . . ? C25 C21 C22 111.5(2) . . ? C20 C21 C22 120.6(2) . . ? C20 C18 N2 114.0(2) . . ? C20 C18 C19 127.1(2) . . ? N2 C18 C19 118.9(2) . . ? F15 C10 F14 108.0(2) . . ? F15 C10 F13 106.7(2) . . ? F14 C10 F13 106.8(2) . . ? F15 C10 C7 112.6(2) . . ? F14 C10 C7 113.1(2) . . ? F13 C10 C7 109.3(2) . . ? C9 C8 C7 122.1(2) . . ? O2 C1 C2 128.7(2) . . ? O2 C1 C5 114.6(2) . . ? C2 C1 C5 116.7(2) . . ? O6 N4 O7 123.6(3) . . ? O6 N4 C34 118.3(3) . . ? O7 N4 C34 118.1(3) . . ? N3 C30 C31 125.5(2) . . ? N3 C30 S2 114.5(2) . . ? C31 C30 S2 119.9(2) . . ? C32 C31 C369 119.1(3) . . ? C32 C31 C30 121.6(2) . . ? C369 C31 C30 119.3(2) . . ? C32 C33 C34 118.8(3) . . ? F18 C11 F17 106.8(2) . . ? F18 C11 F16 106.9(2) . . ? F17 C11 F16 106.5(2) . . ? F18 C11 C9 111.3(2) . . ? F17 C11 C9 114.1(2) . . ? F16 C11 C9 110.9(2) . . ? C21 C25 C26 128.3(2) . . ? C21 C25 C24 109.2(2) . . ? C26 C25 C24 122.3(2) . . ? C34 C35 C369 118.7(3) . . ? O1 C28 C29 111.9(2) . . ? C1 C2 C3 122.5(2) . . ? F6 C22 F5 106.7(2) . . ? F6 C22 C21 112.7(2) . . ? F5 C22 C21 112.1(2) . . ? F6 C22 C23 110.3(2) . . ? F5 C22 C23 111.0(2) . . ? C21 C22 C23 104.1(2) . . ? C14 C15 C16 118.9(2) . . ? C35 C34 C33 122.2(3) . . ? C35 C34 N4 119.1(3) . . ? C33 C34 N4 118.7(3) . . ? O3 C3 C2 129.1(3) . . ? O3 C3 C4 114.0(2) . . ? C2 C3 C4 116.9(2) . . ? F4 C23 F3 108.1(2) . . ? F4 C23 C24 113.1(2) . . ? F3 C23 C24 108.5(2) . . ? F4 C23 C22 113.9(2) . . ? F3 C23 C22 110.0(2) . . ? C24 C23 C22 103.1(2) . . ? F11 C4 F12 106.6(2) . . ? F11 C4 F10 107.4(3) . . ? F12 C4 F10 106.0(2) . . ? F11 C4 C3 111.3(2) . . ? F12 C4 C3 111.8(2) . . ? F10 C4 C3 113.3(2) . . ? F1 C24 F2 106.4(2) . . ? F1 C24 C25 114.6(2) . . ? F2 C24 C25 111.1(2) . . ? F1 C24 C23 111.5(2) . . ? F2 C24 C23 109.4(2) . . ? C25 C24 C23 103.8(2) . . ? C33 C32 C31 120.7(3) . . ? _diffrn_measured_fraction_theta_max 0.693 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.637 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.081 # Attachment 'Yu.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 633202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-[5-ethoxy-2-(4-nitrophenyl)thiazoyl]-2-[4-methyl-2-(2-pyridyl)thiazoyl] perfluorocyclopentene ; _chemical_name_common ; 1-(5-ethoxy-2-(4-nitrophenyl)thiazoyl)-2-(4-methyl-2-(2- pyridyl)thiazoyl) perfluorocyclopentene ; _chemical_melting_point ? _chemical_formula_moiety 'C25 H16 F6 N4 O3 S2' _chemical_formula_sum 'C25 H16 F6 N4 O3 S2' _chemical_formula_weight 598.54 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9782(7) _cell_length_b 12.8551(10) _cell_length_c 23.714(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.789(4) _cell_angle_gamma 90.00 _cell_volume 2429.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 5507 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 29.90 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.070 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'X8 apex Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20728 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6057 _reflns_number_gt 4966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+2.7991P] 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 6057 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C50 C -0.1393(3) 0.20403(17) 0.24419(9) 0.0170(4) Uani 1 1 d . . . H50A H -0.1841 0.1737 0.2772 0.026 Uiso 1 1 calc R . . H50B H -0.1482 0.1551 0.2136 0.026 Uiso 1 1 calc R . . H50C H -0.2013 0.2658 0.2340 0.026 Uiso 1 1 calc R . . S1 S 0.34442(6) 0.29201(4) 0.25066(2) 0.01583(12) Uani 1 1 d . . . S2 S -0.04469(6) -0.05011(4) 0.11079(2) 0.01482(12) Uani 1 1 d . . . F2 F 0.01222(16) 0.29855(9) 0.01709(5) 0.0183(3) Uani 1 1 d . . . F1 F -0.17744(15) 0.36256(10) 0.07026(5) 0.0191(3) Uani 1 1 d . . . F3 F 0.02348(16) 0.51874(9) 0.06695(5) 0.0205(3) Uani 1 1 d . . . F4 F 0.24025(15) 0.42057(10) 0.05474(5) 0.0210(3) Uani 1 1 d . . . O3 O 0.15635(18) 0.06326(11) 0.18221(6) 0.0154(3) Uani 1 1 d . . . F6 F 0.29752(17) 0.45281(11) 0.15985(6) 0.0267(3) Uani 1 1 d . . . F5 F 0.03715(18) 0.48631(10) 0.17446(5) 0.0249(3) Uani 1 1 d . . . N2 N -0.1236(2) 0.12483(13) 0.06388(7) 0.0139(3) Uani 1 1 d . . . C9 C 0.0429(2) 0.06254(15) 0.13930(8) 0.0129(4) Uani 1 1 d . . . N4 N 0.1142(2) 0.20970(13) 0.30847(7) 0.0141(3) Uani 1 1 d . . . O2 O -0.5353(2) -0.24252(13) -0.13207(7) 0.0283(4) Uani 1 1 d . . . N1 N -0.5258(2) -0.14735(15) -0.12820(8) 0.0204(4) Uani 1 1 d . . . C7 C -0.1483(2) 0.02537(15) 0.05885(8) 0.0135(4) Uani 1 1 d . . . O1 O -0.5906(2) -0.08629(14) -0.16233(7) 0.0270(4) Uani 1 1 d . . . C12 C 0.0308(2) 0.25756(15) 0.11709(8) 0.0123(4) Uani 1 1 d . . . C4 C -0.2474(2) -0.02141(16) 0.01181(8) 0.0143(4) Uani 1 1 d . . . C19 C 0.2730(2) 0.23565(15) 0.31075(8) 0.0139(4) Uani 1 1 d . . . C2 C -0.4078(2) 0.00298(17) -0.07629(9) 0.0162(4) Uani 1 1 d . . . H2 H -0.4537 0.0462 -0.1044 0.019 Uiso 1 1 calc R . . C3 C -0.3157(2) 0.04340(16) -0.03065(9) 0.0154(4) Uani 1 1 d . . . H3 H -0.2988 0.1149 -0.0281 0.018 Uiso 1 1 calc R . . C1 C -0.4300(2) -0.10392(17) -0.07901(9) 0.0164(4) Uani 1 1 d . . . C10 C 0.1948(3) -0.03666(16) 0.20901(9) 0.0177(4) Uani 1 1 d . . . H10A H 0.2449 -0.0832 0.1824 0.021 Uiso 1 1 calc R . . H10B H 0.0929 -0.0686 0.2216 0.021 Uiso 1 1 calc R . . C20 C 0.3914(3) 0.21082(16) 0.35809(8) 0.0153(4) Uani 1 1 d . . . C17 C 0.1468(2) 0.27615(15) 0.21911(8) 0.0136(4) Uani 1 1 d . . . C8 C -0.0156(2) 0.14885(15) 0.10941(8) 0.0133(4) Uani 1 1 d . . . N5 N 0.5478(2) 0.24759(14) 0.35432(8) 0.0186(4) Uani 1 1 d . . . C6 C -0.3654(3) -0.17033(17) -0.03796(9) 0.0184(4) Uani 1 1 d . . . H6 H -0.3829 -0.2417 -0.0408 0.022 Uiso 1 1 calc R . . C18 C 0.0410(2) 0.23137(15) 0.25621(8) 0.0132(4) Uani 1 1 d . . . C16 C 0.1072(2) 0.30958(15) 0.16113(8) 0.0132(4) Uani 1 1 d . . . C22 C 0.4612(3) 0.12022(18) 0.44341(9) 0.0226(5) Uani 1 1 d . . . H22 H 0.4326 0.0778 0.4732 0.027 Uiso 1 1 calc R . . C21 C 0.3424(3) 0.14719(17) 0.40165(9) 0.0197(4) Uani 1 1 d . . . H21 H 0.2325 0.1234 0.4027 0.024 Uiso 1 1 calc R . . C15 C 0.1386(3) 0.42157(16) 0.14657(9) 0.0159(4) Uani 1 1 d . . . C5 C -0.2736(3) -0.12862(17) 0.00777(9) 0.0170(4) Uani 1 1 d . . . H5 H -0.2292 -0.1723 0.0359 0.020 Uiso 1 1 calc R . . C13 C -0.0134(2) 0.33350(16) 0.06979(8) 0.0141(4) Uani 1 1 d . . . C23 C 0.6228(3) 0.15706(18) 0.44031(9) 0.0221(5) Uani 1 1 d . . . H23 H 0.7048 0.1402 0.4680 0.027 Uiso 1 1 calc R . . C14 C 0.0973(3) 0.42898(16) 0.08296(9) 0.0151(4) Uani 1 1 d . . . C24 C 0.6605(3) 0.21970(18) 0.39514(9) 0.0213(4) Uani 1 1 d . . . H24 H 0.7700 0.2437 0.3931 0.026 Uiso 1 1 calc R . . C11 C 0.3152(3) -0.01714(18) 0.25857(9) 0.0208(4) Uani 1 1 d . . . H11A H 0.3427 -0.0819 0.2769 0.031 Uiso 1 1 calc R . . H11B H 0.2642 0.0287 0.2847 0.031 Uiso 1 1 calc R . . H11C H 0.4156 0.0143 0.2457 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C50 0.0165(9) 0.0179(10) 0.0167(10) 0.0004(8) 0.0013(8) -0.0034(8) S1 0.0150(2) 0.0191(3) 0.0132(2) 0.00299(19) -0.00194(18) -0.00466(19) S2 0.0171(2) 0.0107(2) 0.0166(2) -0.00003(19) 0.00028(18) -0.00035(18) F2 0.0269(6) 0.0173(6) 0.0107(5) -0.0003(5) 0.0005(5) -0.0001(5) F1 0.0158(6) 0.0202(6) 0.0210(6) 0.0022(5) -0.0021(5) 0.0040(5) F3 0.0290(7) 0.0109(6) 0.0212(6) 0.0045(5) -0.0013(5) 0.0047(5) F4 0.0217(6) 0.0179(6) 0.0242(7) 0.0002(5) 0.0090(5) -0.0028(5) O3 0.0180(7) 0.0119(7) 0.0159(7) 0.0021(6) -0.0031(6) 0.0020(5) F6 0.0260(7) 0.0246(7) 0.0283(7) 0.0082(6) -0.0096(6) -0.0129(6) F5 0.0415(8) 0.0148(6) 0.0189(6) -0.0024(5) 0.0059(6) 0.0048(6) N2 0.0143(8) 0.0139(8) 0.0136(8) -0.0006(7) 0.0013(6) -0.0007(6) C9 0.0128(8) 0.0120(9) 0.0141(9) -0.0004(7) 0.0020(7) -0.0005(7) N4 0.0165(8) 0.0121(8) 0.0136(8) -0.0017(7) -0.0006(6) -0.0005(6) O2 0.0341(9) 0.0244(9) 0.0262(9) -0.0099(7) -0.0012(7) -0.0067(7) N1 0.0174(8) 0.0249(10) 0.0190(9) -0.0065(8) 0.0034(7) -0.0047(7) C7 0.0132(9) 0.0126(9) 0.0148(9) 0.0006(8) 0.0029(7) 0.0007(7) O1 0.0248(8) 0.0337(10) 0.0218(8) -0.0006(7) -0.0060(7) -0.0046(7) C12 0.0123(8) 0.0126(9) 0.0120(9) 0.0014(7) 0.0008(7) 0.0005(7) C4 0.0114(8) 0.0161(10) 0.0157(9) -0.0024(8) 0.0037(7) -0.0013(7) C19 0.0182(9) 0.0112(9) 0.0123(9) 0.0000(7) -0.0004(7) -0.0012(7) C2 0.0148(9) 0.0188(10) 0.0152(9) 0.0002(8) 0.0018(7) 0.0001(8) C3 0.0146(9) 0.0139(10) 0.0179(10) -0.0010(8) 0.0038(8) -0.0022(7) C1 0.0130(9) 0.0218(11) 0.0146(9) -0.0062(8) 0.0024(7) -0.0034(8) C10 0.0241(10) 0.0115(10) 0.0175(10) 0.0023(8) 0.0003(8) 0.0037(8) C20 0.0196(10) 0.0127(9) 0.0133(9) -0.0025(8) -0.0004(7) -0.0007(8) C17 0.0149(9) 0.0117(9) 0.0139(9) -0.0004(8) -0.0024(7) -0.0005(7) C8 0.0143(9) 0.0128(9) 0.0129(9) 0.0002(7) 0.0014(7) -0.0007(7) N5 0.0201(9) 0.0178(9) 0.0175(9) 0.0005(7) -0.0040(7) -0.0035(7) C6 0.0190(10) 0.0151(10) 0.0214(10) -0.0055(8) 0.0051(8) -0.0003(8) C18 0.0146(9) 0.0109(9) 0.0139(9) -0.0006(7) -0.0011(7) 0.0007(7) C16 0.0135(9) 0.0131(9) 0.0129(9) 0.0021(7) 0.0012(7) 0.0007(7) C22 0.0311(12) 0.0215(11) 0.0152(10) 0.0028(9) 0.0024(9) 0.0061(9) C21 0.0211(10) 0.0208(11) 0.0173(10) 0.0020(9) 0.0012(8) 0.0010(8) C15 0.0178(9) 0.0137(10) 0.0158(10) -0.0002(8) -0.0023(8) -0.0016(8) C5 0.0169(9) 0.0164(10) 0.0179(10) -0.0014(8) 0.0018(8) 0.0008(8) C13 0.0162(9) 0.0141(9) 0.0118(9) 0.0010(8) 0.0002(7) 0.0019(7) C23 0.0279(11) 0.0229(11) 0.0148(10) -0.0035(9) -0.0062(9) 0.0077(9) C14 0.0187(9) 0.0113(9) 0.0154(9) 0.0032(8) 0.0015(8) 0.0015(7) C24 0.0199(10) 0.0212(11) 0.0222(11) -0.0027(9) -0.0062(8) -0.0016(8) C11 0.0221(10) 0.0180(10) 0.0217(11) 0.0026(9) -0.0032(9) 0.0046(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 C50 C18 1.495(3) . ? S1 C19 1.720(2) . ? S1 C17 1.724(2) . ? S2 C9 1.731(2) . ? S2 C7 1.744(2) . ? F2 C13 1.353(2) . ? F1 C13 1.362(2) . ? F3 C14 1.342(2) . ? F4 C14 1.354(2) . ? O3 C9 1.329(2) . ? O3 C10 1.459(2) . ? F6 C15 1.352(2) . ? F5 C15 1.356(2) . ? N2 C7 1.298(3) . ? N2 C8 1.383(3) . ? C9 C8 1.385(3) . ? N4 C19 1.309(3) . ? N4 C18 1.372(3) . ? O2 N1 1.229(3) . ? N1 O1 1.224(3) . ? N1 C1 1.473(3) . ? C7 C4 1.465(3) . ? C12 C16 1.359(3) . ? C12 C8 1.455(3) . ? C12 C13 1.515(3) . ? C4 C5 1.397(3) . ? C4 C3 1.397(3) . ? C19 C20 1.467(3) . ? C2 C3 1.380(3) . ? C2 C1 1.387(3) . ? C1 C6 1.376(3) . ? C10 C11 1.502(3) . ? C20 N5 1.341(3) . ? C20 C21 1.389(3) . ? C17 C18 1.375(3) . ? C17 C16 1.460(3) . ? N5 C24 1.338(3) . ? C6 C5 1.386(3) . ? C16 C15 1.504(3) . ? C22 C23 1.379(3) . ? C22 C21 1.381(3) . ? C15 C14 1.531(3) . ? C13 C14 1.536(3) . ? C23 C24 1.385(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 S1 C17 88.68(10) . . ? C9 S2 C7 88.79(10) . . ? C9 O3 C10 116.64(16) . . ? C7 N2 C8 112.18(17) . . ? O3 C9 C8 125.89(18) . . ? O3 C9 S2 123.50(15) . . ? C8 C9 S2 110.53(15) . . ? C19 N4 C18 110.71(17) . . ? O1 N1 O2 124.53(19) . . ? O1 N1 C1 117.82(18) . . ? O2 N1 C1 117.65(19) . . ? N2 C7 C4 123.24(18) . . ? N2 C7 S2 114.74(15) . . ? C4 C7 S2 121.95(15) . . ? C16 C12 C8 132.11(18) . . ? C16 C12 C13 109.34(17) . . ? C8 C12 C13 118.53(17) . . ? C5 C4 C3 119.16(19) . . ? C5 C4 C7 122.06(19) . . ? C3 C4 C7 118.77(18) . . ? N4 C19 C20 124.21(18) . . ? N4 C19 S1 115.60(15) . . ? C20 C19 S1 119.93(15) . . ? C3 C2 C1 118.15(19) . . ? C2 C3 C4 120.99(19) . . ? C6 C1 C2 122.62(19) . . ? C6 C1 N1 119.16(19) . . ? C2 C1 N1 118.22(19) . . ? O3 C10 C11 107.86(17) . . ? N5 C20 C21 123.64(19) . . ? N5 C20 C19 116.02(18) . . ? C21 C20 C19 120.21(19) . . ? C18 C17 C16 127.90(18) . . ? C18 C17 S1 110.42(14) . . ? C16 C17 S1 121.67(15) . . ? N2 C8 C9 113.72(17) . . ? N2 C8 C12 117.21(17) . . ? C9 C8 C12 128.90(18) . . ? C24 N5 C20 116.87(19) . . ? C1 C6 C5 118.6(2) . . ? N4 C18 C17 114.55(17) . . ? N4 C18 C50 119.17(17) . . ? C17 C18 C50 126.27(18) . . ? C12 C16 C17 130.31(18) . . ? C12 C16 C15 111.59(17) . . ? C17 C16 C15 117.84(17) . . ? C23 C22 C21 119.1(2) . . ? C22 C21 C20 118.2(2) . . ? F6 C15 F5 106.22(16) . . ? F6 C15 C16 113.29(17) . . ? F5 C15 C16 111.44(17) . . ? F6 C15 C14 111.43(17) . . ? F5 C15 C14 109.73(16) . . ? C16 C15 C14 104.80(16) . . ? C6 C5 C4 120.5(2) . . ? F2 C13 F1 106.69(15) . . ? F2 C13 C12 115.44(16) . . ? F1 C13 C12 111.09(16) . . ? F2 C13 C14 110.00(16) . . ? F1 C13 C14 108.83(16) . . ? C12 C13 C14 104.69(16) . . ? C22 C23 C24 118.7(2) . . ? F3 C14 F4 107.31(16) . . ? F3 C14 C15 113.74(17) . . ? F4 C14 C15 109.63(16) . . ? F3 C14 C13 112.91(17) . . ? F4 C14 C13 109.01(16) . . ? C15 C14 C13 104.16(16) . . ? N5 C24 C23 123.5(2) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.660 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.088 data_Cu(hfac)2.2a _database_code_depnum_ccdc_archive 'CCDC 633203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Cu [1-[5-ethoxy-2-(4-nitrophenyl)thiazoyl]-2-[4-methyl-2-(2-pyridyl)thiazoyl] perfluorocyclopentene] (hfac)2 ; _chemical_name_common ; Cu (1-(5-ethoxy-2-(4-nitrophenyl)thiazoyl)-2-(4-methyl-2-(2- pyridyl)thiazoyl) perfluorocyclopentene) (hfac)2 ; _chemical_melting_point ? _chemical_formula_moiety 'C35 H18 Cu F18 N4 O7 S2' _chemical_formula_sum 'C35 H18 Cu F18 N4 O7 S2' _chemical_formula_weight 1076.19 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.946(5) _cell_length_b 11.774(5) _cell_length_c 19.493(5) _cell_angle_alpha 92.804(5) _cell_angle_beta 91.091(5) _cell_angle_gamma 105.202(5) _cell_volume 1977.9(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 7043 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 28.05 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1070 _exptl_absorpt_coefficient_mu 0.798 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20257 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.17 _reflns_number_total 8326 _reflns_number_gt 6235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+1.9213P] 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 8326 _refine_ls_number_parameters 604 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.34638(4) 0.17679(3) 0.640150(17) 0.01512(9) Uani 1 1 d . . . S2 S 0.09193(7) 0.16122(6) 0.96691(4) 0.01805(15) Uani 1 1 d . . . S3 S 0.09847(8) -0.18230(6) 0.72596(4) 0.01765(15) Uani 1 1 d . . . F4 F -0.52472(18) -0.33290(16) 0.81140(10) 0.0345(5) Uani 1 1 d . . . F5 F -0.46902(18) -0.10477(16) 0.82983(9) 0.0289(4) Uani 1 1 d . . . F6 F -0.0325(2) 0.27231(15) 0.45452(9) 0.0362(5) Uani 1 1 d . . . F7 F -0.40275(18) -0.15118(15) 0.93010(8) 0.0268(4) Uani 1 1 d . . . F8 F -0.3367(2) -0.33951(15) 0.88152(9) 0.0303(4) Uani 1 1 d . . . F9 F 0.7302(2) 0.25159(15) 0.81097(9) 0.0294(4) Uani 1 1 d . . . F10 F -0.3359(2) -0.25678(17) 0.71427(9) 0.0336(4) Uani 1 1 d . . . F11 F -0.1916(2) -0.34419(14) 0.77037(10) 0.0313(4) Uani 1 1 d . . . F12 F 0.84690(19) 0.47013(17) 0.53656(10) 0.0348(5) Uani 1 1 d . . . F13 F 0.6314(2) 0.44922(16) 0.48171(9) 0.0344(4) Uani 1 1 d . . . F14 F 0.0735(3) 0.1334(2) 0.43308(10) 0.0580(7) Uani 1 1 d . . . F15 F 0.6957(2) 0.57610(15) 0.56674(10) 0.0342(4) Uani 1 1 d . . . F16 F 0.8436(2) 0.42551(18) 0.78224(11) 0.0512(6) Uani 1 1 d . . . F17 F 0.3468(2) 0.55674(16) 0.67508(11) 0.0447(5) Uani 1 1 d . . . F18 F 0.1144(2) 0.54163(15) 0.64044(10) 0.0361(5) Uani 1 1 d . . . O3 O 0.5150(2) 0.29092(17) 0.56799(10) 0.0217(4) Uani 1 1 d . . . O1 O 0.1256(2) -0.02981(17) 0.89114(10) 0.0204(4) Uani 1 1 d . . . F21 F 0.1611(3) 0.47911(19) 0.73801(11) 0.0604(7) Uani 1 1 d . . . F1 F -0.1206(2) 0.10723(18) 0.49714(11) 0.0506(6) Uani 1 1 d . . . F2 F 0.6194(3) 0.39049(19) 0.82592(10) 0.0474(6) Uani 1 1 d . . . O24 O 0.1931(2) 0.15046(15) 0.55970(9) 0.0170(4) Uani 1 1 d . . . C25 C 0.0368(3) 0.0395(2) 0.91066(14) 0.0173(6) Uani 1 1 d . . . O26 O 0.5165(2) 0.22345(16) 0.71114(10) 0.0203(4) Uani 1 1 d . . . N2 N 0.1680(2) 0.03276(19) 0.69418(11) 0.0154(5) Uani 1 1 d . . . O28 O -0.1523(3) 0.6297(2) 1.13770(11) 0.0393(6) Uani 1 1 d . . . N29 N -0.1934(2) 0.09316(19) 0.92338(11) 0.0160(5) Uani 1 1 d . . . C99 C -0.1519(3) -0.1390(2) 0.79559(14) 0.0159(6) Uani 1 1 d . . . O4 O -0.3655(3) 0.5925(2) 1.07694(14) 0.0416(6) Uani 1 1 d . . . C3 C -0.3124(3) 0.3966(3) 1.01387(16) 0.0246(7) Uani 1 1 d . . . H3 H -0.4035 0.4159 1.0019 0.029 Uiso 1 1 calc R . . O2 O 0.2872(2) 0.31637(16) 0.67258(10) 0.0189(4) Uani 1 1 d . . . C34 C 0.1116(3) 0.3258(2) 0.58122(14) 0.0187(6) Uani 1 1 d . . . H34 H 0.0478 0.3699 0.5646 0.022 Uiso 1 1 calc R . . C35 C -0.1189(3) 0.0166(2) 0.89261(13) 0.0151(5) Uani 1 1 d . . . C36 C -0.2635(3) -0.2561(2) 0.77589(15) 0.0204(6) Uani 1 1 d . . . C37 C -0.3799(3) -0.2759(3) 0.83291(15) 0.0228(6) Uani 1 1 d . . . C38 C 0.0383(3) 0.0179(2) 0.73287(14) 0.0166(6) Uani 1 1 d . . . C39 C -0.2021(3) -0.0851(2) 0.84980(14) 0.0156(6) Uani 1 1 d . . . C40 C -0.0987(3) 0.1735(2) 0.96290(14) 0.0169(6) Uani 1 1 d . . . C41 C -0.1388(3) 0.2720(2) 0.99999(14) 0.0171(6) Uani 1 1 d . . . N5 N -0.2471(3) 0.5685(2) 1.09555(13) 0.0280(6) Uani 1 1 d . . . C43 C 0.7057(3) 0.3466(3) 0.78316(16) 0.0248(7) Uani 1 1 d . . . C44 C -0.0156(3) -0.0936(2) 0.75534(14) 0.0163(6) Uani 1 1 d . . . C45 C -0.3663(3) -0.1508(3) 0.86340(14) 0.0192(6) Uani 1 1 d . . . C46 C 0.0098(3) 0.1845(2) 0.48143(15) 0.0206(6) Uani 1 1 d . . . C47 C 0.2108(3) -0.0648(2) 0.68603(14) 0.0160(6) Uani 1 1 d . . . C48 C 0.6979(3) 0.4673(3) 0.54405(15) 0.0220(6) Uani 1 1 d . . . C49 C 0.1160(3) 0.2218(2) 0.54577(14) 0.0160(6) Uani 1 1 d . . . C50 C 0.6202(3) 0.3737(2) 0.59307(15) 0.0188(6) Uani 1 1 d . . . C51 C 0.6805(3) 0.3917(2) 0.66109(15) 0.0229(6) Uani 1 1 d . . . H51 H 0.7613 0.4583 0.6722 0.028 Uiso 1 1 calc R . . C52 C -0.2752(3) 0.3005(2) 0.98194(15) 0.0215(6) Uani 1 1 d . . . H52 H -0.3420 0.2545 0.9481 0.026 Uiso 1 1 calc R . . C53 C -0.0409(3) 0.3404(3) 1.05149(15) 0.0250(7) Uani 1 1 d . . . H53 H 0.0497 0.3212 1.0643 0.030 Uiso 1 1 calc R . . N1 N 0.4186(2) 0.03151(19) 0.61841(11) 0.0141(5) Uani 1 1 d . . . C55 C -0.0299(3) 0.1199(2) 0.74364(15) 0.0219(6) Uani 1 1 d . . . H55A H 0.0325 0.1869 0.7221 0.033 Uiso 1 1 calc R . . H55B H -0.0331 0.1386 0.7920 0.033 Uiso 1 1 calc R . . H55C H -0.1332 0.0999 0.7238 0.033 Uiso 1 1 calc R . . C56 C 0.6262(3) 0.3160(2) 0.71221(14) 0.0181(6) Uani 1 1 d . . . C57 C 0.5178(3) -0.1705(3) 0.59438(15) 0.0236(6) Uani 1 1 d . . . H57 H 0.5495 -0.2387 0.5853 0.028 Uiso 1 1 calc R . . C58 C 0.3441(3) -0.0709(2) 0.64485(14) 0.0163(6) Uani 1 1 d . . . C59 C -0.2114(3) 0.4632(2) 1.06385(15) 0.0215(6) Uani 1 1 d . . . C60 C 0.5968(3) -0.0657(3) 0.56903(15) 0.0219(6) Uani 1 1 d . . . H60 H 0.6843 -0.0614 0.5432 0.026 Uiso 1 1 calc R . . C61 C 0.5445(3) 0.0327(3) 0.58243(14) 0.0199(6) Uani 1 1 d . . . H61 H 0.5995 0.1037 0.5656 0.024 Uiso 1 1 calc R . . C62 C 0.3905(3) -0.1729(2) 0.63354(15) 0.0210(6) Uani 1 1 d . . . H62 H 0.3365 -0.2425 0.6521 0.025 Uiso 1 1 calc R . . C63 C 0.2906(3) 0.0083(3) 0.90991(15) 0.0211(6) Uani 1 1 d . . . H63A H 0.3333 -0.0594 0.9078 0.025 Uiso 1 1 calc R . . H63B H 0.3040 0.0417 0.9568 0.025 Uiso 1 1 calc R . . C64 C -0.0770(3) 0.4365(3) 1.08366(15) 0.0265(7) Uani 1 1 d . . . H64 H -0.0116 0.4822 1.1180 0.032 Uiso 1 1 calc R . . C65 C 0.3772(3) 0.0982(3) 0.86307(16) 0.0255(7) Uani 1 1 d . . . H65A H 0.4850 0.1212 0.8767 0.038 Uiso 1 1 calc R . . H65B H 0.3364 0.1660 0.8657 0.038 Uiso 1 1 calc R . . H65C H 0.3655 0.0649 0.8167 0.038 Uiso 1 1 calc R . . C66 C 0.2006(3) 0.3654(2) 0.64103(14) 0.0171(6) Uani 1 1 d . . . C67 C 0.2026(4) 0.4862(3) 0.67416(16) 0.0261(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01493(16) 0.01502(17) 0.01487(18) -0.00102(13) -0.00182(13) 0.00347(12) S2 0.0145(3) 0.0214(3) 0.0173(4) -0.0018(3) -0.0011(3) 0.0037(3) S3 0.0200(3) 0.0151(3) 0.0190(4) 0.0019(3) 0.0054(3) 0.0061(3) F4 0.0164(8) 0.0411(11) 0.0368(11) -0.0144(9) 0.0004(8) -0.0058(7) F5 0.0178(8) 0.0397(10) 0.0318(10) -0.0040(8) -0.0036(7) 0.0135(7) F6 0.0463(11) 0.0261(10) 0.0347(11) 0.0018(8) -0.0239(9) 0.0087(8) F7 0.0222(8) 0.0338(10) 0.0184(9) -0.0056(7) 0.0060(7) -0.0022(7) F8 0.0352(10) 0.0256(9) 0.0279(10) 0.0069(8) 0.0061(8) 0.0029(8) F9 0.0361(10) 0.0288(9) 0.0257(10) 0.0039(8) -0.0078(8) 0.0132(8) F10 0.0294(9) 0.0456(11) 0.0190(9) -0.0081(8) -0.0060(8) -0.0001(8) F11 0.0294(9) 0.0173(9) 0.0456(12) -0.0030(8) 0.0124(9) 0.0036(7) F12 0.0174(8) 0.0449(11) 0.0462(12) 0.0230(9) 0.0073(8) 0.0110(8) F13 0.0341(10) 0.0382(11) 0.0242(10) 0.0084(8) -0.0073(8) -0.0029(8) F14 0.0589(14) 0.106(2) 0.0249(11) -0.0298(12) -0.0193(10) 0.0570(14) F15 0.0431(11) 0.0215(9) 0.0394(11) 0.0055(8) 0.0031(9) 0.0098(8) F16 0.0459(12) 0.0473(13) 0.0426(12) 0.0129(10) -0.0273(10) -0.0193(10) F17 0.0437(11) 0.0194(9) 0.0668(14) -0.0088(9) -0.0252(10) 0.0048(8) F18 0.0425(10) 0.0244(9) 0.0458(12) -0.0086(8) -0.0155(9) 0.0195(8) O3 0.0207(10) 0.0216(10) 0.0195(11) -0.0009(8) -0.0016(8) 0.0001(8) O1 0.0143(9) 0.0235(10) 0.0235(11) -0.0029(8) 0.0001(8) 0.0062(8) F21 0.120(2) 0.0423(13) 0.0298(13) 0.0017(10) 0.0260(13) 0.0397(14) F1 0.0403(11) 0.0463(13) 0.0461(13) 0.0128(10) -0.0196(10) -0.0230(9) F2 0.0670(14) 0.0616(14) 0.0257(11) -0.0162(10) -0.0103(10) 0.0427(12) O24 0.0183(9) 0.0152(9) 0.0175(10) -0.0005(8) -0.0018(8) 0.0047(7) C25 0.0170(12) 0.0196(14) 0.0145(14) 0.0015(11) 0.0026(11) 0.0033(10) O26 0.0206(9) 0.0179(10) 0.0206(11) 0.0006(8) -0.0021(8) 0.0022(8) N2 0.0180(11) 0.0161(11) 0.0122(12) -0.0012(9) 0.0001(9) 0.0048(9) O28 0.0640(16) 0.0292(12) 0.0249(12) -0.0092(10) -0.0137(12) 0.0157(11) N29 0.0165(10) 0.0185(11) 0.0127(12) -0.0002(9) 0.0007(9) 0.0039(9) C99 0.0157(12) 0.0166(13) 0.0160(14) 0.0006(11) -0.0011(11) 0.0053(10) O4 0.0313(12) 0.0366(14) 0.0588(17) -0.0144(12) -0.0010(12) 0.0155(11) C3 0.0201(13) 0.0255(15) 0.0279(17) -0.0025(13) 0.0007(13) 0.0065(12) O2 0.0217(9) 0.0192(10) 0.0159(10) -0.0010(8) -0.0034(8) 0.0061(8) C34 0.0196(13) 0.0186(14) 0.0185(15) 0.0002(11) -0.0023(12) 0.0064(11) C35 0.0154(12) 0.0189(13) 0.0111(13) 0.0018(11) 0.0026(11) 0.0041(10) C36 0.0214(13) 0.0204(14) 0.0187(15) -0.0020(12) -0.0002(12) 0.0049(11) C37 0.0165(13) 0.0268(15) 0.0219(16) -0.0025(13) -0.0006(12) 0.0007(11) C38 0.0183(13) 0.0179(13) 0.0140(14) -0.0028(11) -0.0019(11) 0.0064(10) C39 0.0125(12) 0.0195(13) 0.0154(14) 0.0016(11) -0.0004(11) 0.0053(10) C40 0.0161(12) 0.0200(14) 0.0153(14) 0.0027(11) 0.0019(11) 0.0054(11) C41 0.0199(13) 0.0188(14) 0.0120(14) 0.0008(11) 0.0029(11) 0.0040(11) N5 0.0352(14) 0.0232(13) 0.0249(14) -0.0010(11) 0.0012(12) 0.0071(11) C43 0.0258(14) 0.0210(15) 0.0257(17) 0.0014(12) -0.0056(13) 0.0032(12) C44 0.0187(13) 0.0179(13) 0.0137(14) -0.0009(11) 0.0000(11) 0.0075(11) C45 0.0136(12) 0.0289(15) 0.0140(15) -0.0023(12) 0.0011(11) 0.0040(11) C46 0.0178(13) 0.0212(14) 0.0224(16) -0.0016(12) -0.0027(12) 0.0053(11) C47 0.0173(12) 0.0172(13) 0.0127(14) -0.0018(11) -0.0012(11) 0.0035(10) C48 0.0170(13) 0.0243(15) 0.0247(16) 0.0033(12) -0.0045(12) 0.0055(11) C49 0.0134(12) 0.0161(13) 0.0168(14) 0.0032(11) 0.0015(11) 0.0004(10) C50 0.0161(12) 0.0191(14) 0.0220(15) 0.0008(12) 0.0010(12) 0.0059(11) C51 0.0201(13) 0.0206(14) 0.0249(17) 0.0012(12) -0.0060(13) 0.0001(11) C52 0.0167(13) 0.0225(15) 0.0232(16) -0.0052(12) -0.0011(12) 0.0027(11) C53 0.0232(14) 0.0291(16) 0.0232(16) -0.0050(13) -0.0082(13) 0.0094(12) N1 0.0145(10) 0.0156(11) 0.0123(12) 0.0008(9) 0.0015(9) 0.0039(9) C55 0.0264(14) 0.0195(14) 0.0227(16) 0.0031(12) 0.0066(13) 0.0103(12) C56 0.0174(13) 0.0171(13) 0.0204(15) -0.0023(11) -0.0022(12) 0.0066(11) C57 0.0274(15) 0.0236(15) 0.0230(16) -0.0006(12) 0.0016(13) 0.0126(12) C58 0.0169(12) 0.0185(13) 0.0129(14) -0.0010(11) -0.0016(11) 0.0044(10) C59 0.0269(14) 0.0202(14) 0.0167(15) -0.0020(12) 0.0046(12) 0.0052(12) C60 0.0191(13) 0.0284(16) 0.0209(16) 0.0036(13) 0.0057(12) 0.0100(12) C61 0.0180(13) 0.0237(15) 0.0182(15) 0.0060(12) 0.0047(12) 0.0046(11) C62 0.0243(14) 0.0178(14) 0.0214(16) 0.0027(12) 0.0048(12) 0.0057(11) C63 0.0143(12) 0.0311(16) 0.0194(15) -0.0011(12) -0.0008(12) 0.0093(11) C64 0.0311(16) 0.0280(16) 0.0192(16) -0.0075(13) -0.0056(13) 0.0077(13) C65 0.0182(13) 0.0304(16) 0.0264(17) 0.0009(13) 0.0043(13) 0.0037(12) C66 0.0183(13) 0.0142(13) 0.0180(15) 0.0006(11) 0.0030(12) 0.0029(10) C67 0.0387(17) 0.0183(15) 0.0221(17) -0.0015(12) -0.0033(14) 0.0095(13) _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 Cu1 O2 1.936(2) . ? Cu1 O26 1.9852(19) . ? Cu1 N1 2.011(2) . ? Cu1 O24 2.0206(18) . ? Cu1 O3 2.294(2) . ? Cu1 N2 2.313(2) . ? S2 C25 1.719(3) . ? S2 C40 1.749(3) . ? S3 C47 1.714(3) . ? S3 C44 1.727(3) . ? F4 C37 1.342(3) . ? F5 C45 1.356(3) . ? F6 C46 1.319(3) . ? F7 C45 1.347(3) . ? F8 C37 1.347(3) . ? F9 C43 1.333(3) . ? F10 C36 1.353(3) . ? F11 C36 1.357(3) . ? F12 C48 1.336(3) . ? F13 C48 1.325(3) . ? F14 C46 1.311(3) . ? F15 C48 1.340(3) . ? F16 C43 1.337(3) . ? F17 C67 1.338(4) . ? F18 C67 1.332(3) . ? O3 C50 1.237(3) . ? O1 C25 1.328(3) . ? O1 C63 1.459(3) . ? F21 C67 1.306(4) . ? F1 C46 1.329(3) . ? F2 C43 1.322(4) . ? O24 C49 1.255(3) . ? C25 C35 1.383(4) . ? O26 C56 1.260(3) . ? N2 C47 1.306(3) . ? N2 C38 1.373(4) . ? O28 N5 1.228(3) . ? N29 C40 1.300(3) . ? N29 C35 1.375(3) . ? C99 C39 1.350(4) . ? C99 C44 1.457(4) . ? C99 C36 1.503(4) . ? O4 N5 1.219(3) . ? C3 C59 1.379(4) . ? C3 C52 1.384(4) . ? O2 C66 1.250(3) . ? C34 C49 1.387(4) . ? C34 C66 1.388(4) . ? C35 C39 1.448(4) . ? C36 C37 1.522(4) . ? C37 C45 1.534(4) . ? C38 C44 1.371(4) . ? C38 C55 1.492(4) . ? C39 C45 1.504(4) . ? C40 C41 1.465(4) . ? C41 C52 1.391(4) . ? C41 C53 1.393(4) . ? N5 C59 1.470(4) . ? C43 C56 1.525(4) . ? C46 C49 1.533(4) . ? C47 C58 1.465(4) . ? C48 C50 1.529(4) . ? C50 C51 1.407(4) . ? C51 C56 1.379(4) . ? C53 C64 1.381(4) . ? N1 C61 1.335(3) . ? N1 C58 1.348(3) . ? C57 C60 1.372(4) . ? C57 C62 1.378(4) . ? C58 C62 1.379(4) . ? C59 C64 1.373(4) . ? C60 C61 1.375(4) . ? C63 C65 1.498(4) . ? C66 C67 1.529(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 O2 Cu1 O26 86.14(8) . . ? O2 Cu1 N1 172.85(8) . . ? O26 Cu1 N1 87.56(8) . . ? O2 Cu1 O24 91.32(7) . . ? O26 Cu1 O24 170.98(8) . . ? N1 Cu1 O24 95.41(8) . . ? O2 Cu1 O3 88.76(8) . . ? O26 Cu1 O3 86.46(8) . . ? N1 Cu1 O3 94.22(9) . . ? O24 Cu1 O3 84.84(8) . . ? O2 Cu1 N2 100.64(8) . . ? O26 Cu1 N2 101.28(8) . . ? N1 Cu1 N2 77.30(9) . . ? O24 Cu1 N2 87.69(8) . . ? O3 Cu1 N2 168.13(7) . . ? C25 S2 C40 88.78(13) . . ? C47 S3 C44 89.14(14) . . ? C50 O3 Cu1 118.89(18) . . ? C25 O1 C63 118.3(2) . . ? C49 O24 Cu1 123.24(17) . . ? O1 C25 C35 123.7(2) . . ? O1 C25 S2 125.65(19) . . ? C35 C25 S2 110.4(2) . . ? C56 O26 Cu1 125.27(18) . . ? C47 N2 C38 111.7(2) . . ? C47 N2 Cu1 107.19(18) . . ? C38 N2 Cu1 141.08(17) . . ? C40 N29 C35 111.4(2) . . ? C39 C99 C44 128.1(2) . . ? C39 C99 C36 111.0(2) . . ? C44 C99 C36 120.8(2) . . ? C59 C3 C52 118.5(3) . . ? C66 O2 Cu1 125.87(17) . . ? C49 C34 C66 121.2(2) . . ? N29 C35 C25 114.6(2) . . ? N29 C35 C39 121.7(2) . . ? C25 C35 C39 123.5(2) . . ? F10 C36 F11 105.9(2) . . ? F10 C36 C99 112.4(2) . . ? F11 C36 C99 112.1(2) . . ? F10 C36 C37 110.6(2) . . ? F11 C36 C37 111.4(2) . . ? C99 C36 C37 104.7(2) . . ? F4 C37 F8 107.3(2) . . ? F4 C37 C36 113.9(2) . . ? F8 C37 C36 110.2(2) . . ? F4 C37 C45 113.1(2) . . ? F8 C37 C45 109.0(2) . . ? C36 C37 C45 103.3(2) . . ? C44 C38 N2 114.1(2) . . ? C44 C38 C55 127.8(3) . . ? N2 C38 C55 118.1(2) . . ? C99 C39 C35 128.9(2) . . ? C99 C39 C45 109.2(2) . . ? C35 C39 C45 121.9(2) . . ? N29 C40 C41 125.2(2) . . ? N29 C40 S2 114.8(2) . . ? C41 C40 S2 119.93(19) . . ? C52 C41 C53 119.2(3) . . ? C52 C41 C40 119.3(2) . . ? C53 C41 C40 121.4(2) . . ? O4 N5 O28 123.8(3) . . ? O4 N5 C59 118.5(2) . . ? O28 N5 C59 117.6(3) . . ? F2 C43 F9 107.0(3) . . ? F2 C43 F16 107.2(3) . . ? F9 C43 F16 106.5(2) . . ? F2 C43 C56 111.1(2) . . ? F9 C43 C56 111.4(2) . . ? F16 C43 C56 113.2(3) . . ? C38 C44 C99 127.8(2) . . ? C38 C44 S3 110.2(2) . . ? C99 C44 S3 121.9(2) . . ? F7 C45 F5 106.7(2) . . ? F7 C45 C39 114.7(2) . . ? F5 C45 C39 111.1(2) . . ? F7 C45 C37 111.6(2) . . ? F5 C45 C37 109.0(2) . . ? C39 C45 C37 103.8(2) . . ? F14 C46 F6 107.7(3) . . ? F14 C46 F1 107.1(3) . . ? F6 C46 F1 105.9(2) . . ? F14 C46 C49 112.3(2) . . ? F6 C46 C49 113.6(2) . . ? F1 C46 C49 109.8(2) . . ? N2 C47 C58 121.4(2) . . ? N2 C47 S3 114.9(2) . . ? C58 C47 S3 123.7(2) . . ? F13 C48 F12 106.9(2) . . ? F13 C48 F15 106.8(2) . . ? F12 C48 F15 106.1(2) . . ? F13 C48 C50 112.8(2) . . ? F12 C48 C50 111.5(2) . . ? F15 C48 C50 112.3(2) . . ? O24 C49 C34 129.0(2) . . ? O24 C49 C46 113.9(2) . . ? C34 C49 C46 117.0(2) . . ? O3 C50 C51 128.2(3) . . ? O3 C50 C48 116.4(2) . . ? C51 C50 C48 115.4(2) . . ? C56 C51 C50 123.6(3) . . ? C3 C52 C41 120.6(3) . . ? C64 C53 C41 120.7(3) . . ? C61 N1 C58 117.6(2) . . ? C61 N1 Cu1 123.00(18) . . ? C58 N1 Cu1 119.28(18) . . ? O26 C56 C51 130.6(3) . . ? O26 C56 C43 112.1(2) . . ? C51 C56 C43 117.3(2) . . ? C60 C57 C62 118.8(3) . . ? N1 C58 C62 122.2(2) . . ? N1 C58 C47 114.7(2) . . ? C62 C58 C47 123.2(2) . . ? C64 C59 C3 122.4(3) . . ? C64 C59 N5 119.0(2) . . ? C3 C59 N5 118.6(3) . . ? C57 C60 C61 118.9(3) . . ? N1 C61 C60 123.2(3) . . ? C57 C62 C58 119.3(3) . . ? O1 C63 C65 111.6(2) . . ? C59 C64 C53 118.6(3) . . ? O2 C66 C34 128.7(2) . . ? O2 C66 C67 112.4(2) . . ? C34 C66 C67 118.9(2) . . ? F21 C67 F18 108.8(3) . . ? F21 C67 F17 106.6(3) . . ? F18 C67 F17 106.1(2) . . ? F21 C67 C66 111.7(2) . . ? F18 C67 C66 113.6(2) . . ? F17 C67 C66 109.7(2) . . ? _diffrn_measured_fraction_theta_max 0.778 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.876 _refine_diff_density_min -0.681 _refine_diff_density_rms 0.074 data_Ag(2a)2.CF3SO3 _database_code_depnum_ccdc_archive 'CCDC 633204' _audit_creation_method SHELXL-97 _chemical_name_systematic ;Ag [1-[5-ethoxy-2-(4-nitrophenyl)thiazoyl]-2-[4-methyl-2-(2-pyridyl)thiazoyl] perfluorocyclopentene]2 (CF3SO3)2 ; _chemical_name_common ; Ag (1-(5-ethoxy-2-(4-nitrophenyl)thiazoyl)-2-(4-methyl-2-(2- pyridyl)thiazoyl) perfluorocyclopentene)2 (CF3SO3)2 ; _chemical_melting_point ? _chemical_formula_moiety 'C51 H32 Ag F15 N8 O9 S5' _chemical_formula_sum 'C51 H32 Ag F15 N8 O9 S5' _chemical_formula_weight 1454.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 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 25.685(5) _cell_length_b 14.069(5) _cell_length_c 16.562(5) _cell_angle_alpha 90. _cell_angle_beta 114.662(5) _cell_angle_gamma 90. _cell_volume 5439(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 5635 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 33.64 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2912 _exptl_absorpt_coefficient_mu 0.680 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28797 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 34.84 _reflns_number_total 9676 _reflns_number_gt 7529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+16.1118P] 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 9676 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.0000 0.083151(14) 0.7500 0.02394(5) Uani 1 2 d S . . S2 S 0.04792(2) 0.21174(3) 0.52589(3) 0.02276(9) Uani 1 1 d . . . S1 S 0.06105(2) 0.60690(3) 0.59683(3) 0.02091(9) Uani 1 1 d . . . F5 F 0.22489(6) 0.16470(9) 0.69949(9) 0.0334(3) Uani 1 1 d . . . F6 F 0.24548(5) 0.47679(9) 0.68412(9) 0.0296(3) Uani 1 1 d . . . F7 F 0.20078(6) 0.19133(10) 0.55909(9) 0.0336(3) Uani 1 1 d . . . C8 C 0.03711(7) 0.49931(12) 0.62109(12) 0.0179(3) Uani 1 1 d . . . O9 O 0.15877(6) 0.58988(9) 0.57517(10) 0.0241(3) Uani 1 1 d . . . F4 F 0.21663(5) 0.42917(9) 0.54690(9) 0.0286(3) Uani 1 1 d . . . N3 N 0.04604(7) 0.13868(10) 0.66543(11) 0.0204(3) Uani 1 1 d . . . C12 C -0.01705(8) 0.49443(13) 0.63074(12) 0.0192(3) Uani 1 1 d . . . C80 C 0.11950(8) 0.54752(12) 0.59559(13) 0.0194(3) Uani 1 1 d . . . C1 C 0.20867(9) 0.23403(14) 0.63707(14) 0.0249(4) Uani 1 1 d . . . N2 N 0.07029(6) 0.42702(10) 0.62855(11) 0.0183(3) Uani 1 1 d . . . C17 C 0.01547(8) 0.14682(12) 0.57970(13) 0.0204(3) Uani 1 1 d . . . F1 F 0.29056(6) 0.29865(11) 0.62115(11) 0.0429(4) Uani 1 1 d . . . C20 C 0.16065(7) 0.38029(13) 0.62359(12) 0.0187(3) Uani 1 1 d . . . C21 C 0.11830(7) 0.45247(12) 0.61547(12) 0.0179(3) Uani 1 1 d . . . C22 C 0.15572(8) 0.28508(13) 0.62990(13) 0.0202(3) Uani 1 1 d . . . C23 C 0.10612(8) 0.22933(12) 0.62532(13) 0.0193(3) Uani 1 1 d . . . C24 C 0.09822(8) 0.18325(12) 0.69219(13) 0.0194(3) Uani 1 1 d . . . F2 F 0.28488(6) 0.31616(11) 0.74779(10) 0.0401(3) Uani 1 1 d . . . C26 C 0.25419(8) 0.31216(16) 0.65912(15) 0.0280(4) Uani 1 1 d . . . C27 C -0.04149(8) 0.10274(13) 0.53250(14) 0.0233(4) Uani 1 1 d . . . C28 C -0.11872(8) 0.48353(15) 0.64853(14) 0.0239(4) Uani 1 1 d . . . C29 C -0.03803(8) 0.40642(13) 0.64181(14) 0.0229(4) Uani 1 1 d . . . H29 H -0.0176 0.3514 0.6431 0.028 Uiso 1 1 calc R . . C30 C 0.15501(9) 0.69253(14) 0.56665(15) 0.0276(4) Uani 1 1 d . . . H30A H 0.1587 0.7213 0.6220 0.033 Uiso 1 1 calc R . . H30B H 0.1184 0.7110 0.5202 0.033 Uiso 1 1 calc R . . C31 C -0.06554(9) 0.09083(15) 0.44093(15) 0.0286(4) Uani 1 1 d . . . H31 H -0.0462 0.1108 0.4073 0.034 Uiso 1 1 calc R . . N4 N -0.06744(8) 0.07456(15) 0.58404(13) 0.0334(4) Uani 1 1 d . . . C33 C -0.08922(8) 0.40051(14) 0.65094(15) 0.0256(4) Uani 1 1 d . . . H33 H -0.1034 0.3420 0.6585 0.031 Uiso 1 1 calc R . . C34 C 0.21908(8) 0.40490(14) 0.62760(14) 0.0227(4) Uani 1 1 d . . . C35 C -0.04764(10) 0.57682(15) 0.62961(16) 0.0306(5) Uani 1 1 d . . . H35 H -0.0336 0.6358 0.6228 0.037 Uiso 1 1 calc R . . N1 N -0.17329(8) 0.47770(14) 0.65725(13) 0.0303(4) Uani 1 1 d . . . O37 O -0.19382(7) 0.39909(13) 0.65676(13) 0.0399(4) Uani 1 1 d . . . C38 C 0.14022(9) 0.17610(14) 0.78685(14) 0.0254(4) Uani 1 1 d . . . H38A H 0.1237 0.1401 0.8196 0.038 Uiso 1 1 calc R . . H38B H 0.1497 0.2387 0.8118 0.038 Uiso 1 1 calc R . . H38C H 0.1743 0.1449 0.7901 0.038 Uiso 1 1 calc R . . O39 O -0.19524(9) 0.55129(14) 0.66552(16) 0.0538(6) Uani 1 1 d . . . C41 C 0.20299(9) 0.72446(16) 0.54386(17) 0.0341(5) Uani 1 1 d . . . H41A H 0.2018 0.7924 0.5376 0.051 Uiso 1 1 calc R . . H41B H 0.1988 0.6956 0.4890 0.051 Uiso 1 1 calc R . . H41C H 0.2390 0.7059 0.5904 0.051 Uiso 1 1 calc R . . C42 C -0.09891(10) 0.57136(16) 0.63857(17) 0.0332(5) Uani 1 1 d . . . H42 H -0.1194 0.6261 0.6378 0.040 Uiso 1 1 calc R . . C43 C -0.11898(10) 0.04849(16) 0.40081(17) 0.0350(5) Uani 1 1 d . . . H43 H -0.1362 0.0397 0.3396 0.042 Uiso 1 1 calc R . . C44 C -0.14625(10) 0.01963(18) 0.45268(18) 0.0402(6) Uani 1 1 d . . . H44 H -0.1823 -0.0084 0.4272 0.048 Uiso 1 1 calc R . . C50 C -0.11891(11) 0.0332(2) 0.5434(2) 0.0447(7) Uani 1 1 d . . . H50 H -0.1372 0.0124 0.5782 0.054 Uiso 1 1 calc R . . S3 S 0.0000 -0.16404(5) 0.7500 0.0476(3) Uani 1 2 d S . . F21 F -0.09165(12) -0.08713(17) 0.72231(19) 0.0320(6) Uani 0.50 1 d P . . F22 F -0.08666(11) -0.23869(18) 0.74326(18) 0.0311(5) Uani 0.50 1 d P . . F23 F -0.09719(11) -0.1818(2) 0.61699(17) 0.0328(6) Uani 0.50 1 d P . . C66 C -0.07114(18) -0.1684(3) 0.7039(3) 0.0239(7) Uani 0.50 1 d P . . O21 O -0.01639(14) -0.07683(19) 0.7944(2) 0.0297(6) Uani 0.50 1 d P . . O22 O -0.02048(13) -0.24863(19) 0.7921(2) 0.0280(6) Uani 0.50 1 d P . . O23 O -0.02582(14) -0.1627(3) 0.6609(2) 0.0358(7) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.03631(12) 0.01866(8) 0.01949(12) 0.000 0.01424(9) 0.000 S2 0.0234(2) 0.0291(2) 0.0162(2) 0.00495(16) 0.00866(18) 0.00771(17) S1 0.0213(2) 0.01831(18) 0.0220(3) -0.00026(15) 0.00797(18) 0.00369(14) F5 0.0329(6) 0.0314(6) 0.0386(8) 0.0151(5) 0.0177(6) 0.0185(5) F6 0.0197(5) 0.0337(6) 0.0293(7) -0.0020(5) 0.0043(5) -0.0007(5) F7 0.0358(7) 0.0375(7) 0.0339(8) -0.0037(5) 0.0207(6) 0.0095(5) C8 0.0190(7) 0.0200(7) 0.0129(9) -0.0002(6) 0.0049(6) 0.0039(6) O9 0.0216(6) 0.0216(6) 0.0292(8) 0.0045(5) 0.0107(6) 0.0015(5) F4 0.0249(6) 0.0395(7) 0.0242(7) 0.0077(5) 0.0131(5) 0.0031(5) N3 0.0264(8) 0.0171(6) 0.0174(9) -0.0015(5) 0.0087(6) 0.0007(5) C12 0.0194(8) 0.0246(8) 0.0128(9) 0.0004(6) 0.0059(7) 0.0067(6) C80 0.0175(7) 0.0207(7) 0.0168(10) -0.0002(6) 0.0041(7) 0.0020(6) C1 0.0258(9) 0.0266(9) 0.0255(11) 0.0053(7) 0.0137(8) 0.0111(7) N2 0.0174(6) 0.0211(7) 0.0156(8) -0.0002(5) 0.0062(6) 0.0037(5) C17 0.0234(8) 0.0204(7) 0.0181(10) -0.0013(6) 0.0095(7) 0.0056(6) F1 0.0298(7) 0.0476(8) 0.0632(11) 0.0084(7) 0.0313(7) 0.0121(6) C20 0.0163(7) 0.0236(8) 0.0153(9) 0.0031(6) 0.0058(7) 0.0036(6) C21 0.0164(7) 0.0209(7) 0.0151(9) 0.0010(6) 0.0052(6) 0.0035(6) C22 0.0204(8) 0.0236(8) 0.0182(10) 0.0047(6) 0.0095(7) 0.0084(6) C23 0.0205(8) 0.0187(7) 0.0188(10) 0.0030(6) 0.0083(7) 0.0068(6) C24 0.0239(8) 0.0152(7) 0.0187(10) 0.0005(6) 0.0084(7) 0.0034(6) F2 0.0282(7) 0.0472(8) 0.0300(8) 0.0090(6) -0.0027(6) 0.0100(6) C26 0.0197(8) 0.0366(10) 0.0284(12) 0.0065(8) 0.0106(8) 0.0111(7) C27 0.0252(9) 0.0225(8) 0.0211(11) -0.0053(6) 0.0085(8) 0.0042(6) C28 0.0196(8) 0.0345(9) 0.0182(10) 0.0020(7) 0.0084(7) 0.0090(7) C29 0.0178(8) 0.0234(8) 0.0257(11) -0.0060(7) 0.0071(7) 0.0022(6) C30 0.0295(10) 0.0210(8) 0.0302(12) -0.0044(7) 0.0105(9) -0.0037(7) C31 0.0318(10) 0.0288(9) 0.0200(11) -0.0020(7) 0.0056(8) 0.0079(8) N4 0.0332(9) 0.0434(10) 0.0271(11) -0.0158(8) 0.0159(8) -0.0111(8) C33 0.0203(8) 0.0277(9) 0.0279(12) -0.0066(7) 0.0092(8) -0.0002(7) C34 0.0189(8) 0.0280(9) 0.0196(10) 0.0033(7) 0.0066(7) 0.0027(6) C35 0.0374(11) 0.0265(9) 0.0385(13) 0.0132(8) 0.0263(10) 0.0160(8) N1 0.0256(8) 0.0410(10) 0.0283(11) 0.0033(7) 0.0152(8) 0.0096(7) O37 0.0276(8) 0.0444(10) 0.0518(12) -0.0057(8) 0.0206(8) -0.0011(7) C38 0.0287(9) 0.0252(9) 0.0187(11) 0.0020(7) 0.0063(8) -0.0043(7) O39 0.0533(12) 0.0454(10) 0.0855(17) 0.0133(10) 0.0516(12) 0.0219(9) C41 0.0263(10) 0.0287(10) 0.0429(15) 0.0014(9) 0.0103(10) -0.0073(8) C42 0.0363(11) 0.0352(11) 0.0394(14) 0.0160(9) 0.0269(11) 0.0205(9) C43 0.0315(11) 0.0328(10) 0.0284(13) -0.0102(8) 0.0003(9) 0.0083(8) C44 0.0269(10) 0.0405(12) 0.0467(16) -0.0251(11) 0.0089(10) -0.0037(9) C50 0.0363(12) 0.0569(16) 0.0480(17) -0.0286(13) 0.0247(12) -0.0191(11) S3 0.0656(6) 0.0161(3) 0.0289(5) 0.000 -0.0121(4) 0.000 F21 0.0386(14) 0.0270(11) 0.0386(16) 0.0012(10) 0.0241(12) 0.0073(10) F22 0.0345(13) 0.0295(12) 0.0337(15) 0.0049(10) 0.0185(12) -0.0034(10) F23 0.0280(12) 0.0506(16) 0.0201(14) -0.0014(11) 0.0103(11) 0.0041(11) C66 0.033(2) 0.0213(16) 0.020(2) 0.0014(13) 0.0141(17) 0.0022(14) O21 0.0412(17) 0.0193(12) 0.0376(19) -0.0020(11) 0.0254(15) -0.0010(11) O22 0.0295(14) 0.0191(12) 0.0324(18) 0.0040(11) 0.0100(13) -0.0025(10) O23 0.0341(17) 0.0473(19) 0.0208(19) 0.0028(13) 0.0064(14) 0.0055(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N3 2.3136(16) 2_556 ? Ag1 N3 2.3136(16) . ? Ag1 O21 2.458(3) 2_556 ? Ag1 O21 2.458(3) . ? Ag1 N4 2.568(2) . ? Ag1 N4 2.568(2) 2_556 ? S2 C17 1.7155(19) . ? S2 C23 1.719(2) . ? S1 C80 1.7258(18) . ? S1 C8 1.7427(19) . ? F5 C1 1.354(2) . ? F6 C34 1.353(2) . ? F7 C1 1.361(2) . ? C8 N2 1.299(2) . ? C8 C12 1.467(2) . ? O9 C80 1.331(2) . ? O9 C30 1.450(2) . ? F4 C34 1.355(2) . ? N3 C17 1.310(3) . ? N3 C24 1.375(2) . ? C12 C35 1.396(2) . ? C12 C29 1.393(3) . ? C80 C21 1.381(2) . ? C1 C22 1.498(2) . ? C1 C26 1.534(3) . ? N2 C21 1.385(2) . ? C17 C27 1.477(3) . ? F1 C26 1.340(2) . ? C20 C22 1.354(3) . ? C20 C21 1.453(2) . ? C20 C34 1.514(3) . ? C22 C23 1.471(3) . ? C23 C24 1.370(3) . ? C24 C38 1.490(3) . ? F2 C26 1.347(3) . ? C26 C34 1.548(3) . ? C27 N4 1.344(3) . ? C27 C31 1.389(3) . ? C28 C42 1.372(3) . ? C28 C33 1.384(3) . ? C28 N1 1.470(2) . ? C29 C33 1.387(3) . ? C30 C41 1.500(3) . ? C31 C43 1.385(3) . ? N4 C50 1.341(3) . ? C35 C42 1.387(3) . ? N1 O39 1.214(2) . ? N1 O37 1.224(3) . ? C43 C44 1.377(4) . ? C44 C50 1.380(4) . ? S3 O23 1.342(3) 2_556 ? S3 O23 1.342(3) . ? S3 O21 1.576(3) . ? S3 O21 1.576(3) 2_556 ? S3 O22 1.576(3) 2_556 ? S3 O22 1.576(3) . ? S3 C66 1.662(4) 2_556 ? S3 C66 1.662(4) . ? F21 C66 1.346(4) . ? F22 C66 1.334(4) . ? F22 O22 1.554(4) . ? F23 C66 1.324(5) . ? F23 O23 1.688(4) . ? C66 O23 1.600(5) . ? C66 O22 1.874(5) . ? O21 O23 1.585(5) 2_556 ? O22 O23 1.646(4) 2_556 ? O23 O21 1.585(5) 2_556 ? O23 O22 1.646(4) 2_556 ? 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 N3 Ag1 N3 140.53(7) 2_556 . ? N3 Ag1 O21 133.24(8) 2_556 2_556 ? N3 Ag1 O21 86.17(8) . 2_556 ? N3 Ag1 O21 86.17(8) 2_556 . ? N3 Ag1 O21 133.24(8) . . ? O21 Ag1 O21 47.43(14) 2_556 . ? N3 Ag1 N4 112.14(6) 2_556 . ? N3 Ag1 N4 69.81(6) . . ? O21 Ag1 N4 76.10(9) 2_556 . ? O21 Ag1 N4 98.86(9) . . ? N3 Ag1 N4 69.81(6) 2_556 2_556 ? N3 Ag1 N4 112.14(6) . 2_556 ? O21 Ag1 N4 98.86(9) 2_556 2_556 ? O21 Ag1 N4 76.10(9) . 2_556 ? N4 Ag1 N4 174.60(9) . 2_556 ? C17 S2 C23 89.76(9) . . ? C80 S1 C8 88.55(8) . . ? N2 C8 C12 124.56(16) . . ? N2 C8 S1 114.92(13) . . ? C12 C8 S1 120.52(13) . . ? C80 O9 C30 116.37(15) . . ? C17 N3 C24 111.87(16) . . ? C17 N3 Ag1 117.34(13) . . ? C24 N3 Ag1 129.39(13) . . ? C35 C12 C29 119.56(17) . . ? C35 C12 C8 120.91(17) . . ? C29 C12 C8 119.52(15) . . ? O9 C80 C21 126.10(16) . . ? O9 C80 S1 122.78(13) . . ? C21 C80 S1 111.09(13) . . ? F5 C1 F7 106.45(16) . . ? F5 C1 C22 112.69(15) . . ? F7 C1 C22 111.45(17) . . ? F5 C1 C26 111.91(17) . . ? F7 C1 C26 109.83(16) . . ? C22 C1 C26 104.59(15) . . ? C8 N2 C21 111.97(15) . . ? N3 C17 C27 123.40(17) . . ? N3 C17 S2 114.10(14) . . ? C27 C17 S2 122.49(15) . . ? C22 C20 C21 127.47(16) . . ? C22 C20 C34 110.22(15) . . ? C21 C20 C34 122.30(16) . . ? C80 C21 N2 113.44(15) . . ? C80 C21 C20 127.49(16) . . ? N2 C21 C20 119.07(15) . . ? C20 C22 C23 129.09(16) . . ? C20 C22 C1 111.68(16) . . ? C23 C22 C1 119.11(16) . . ? C24 C23 C22 128.91(18) . . ? C24 C23 S2 110.09(14) . . ? C22 C23 S2 120.98(14) . . ? C23 C24 N3 114.12(17) . . ? C23 C24 C38 126.60(17) . . ? N3 C24 C38 119.26(16) . . ? F1 C26 F2 108.19(17) . . ? F1 C26 C1 113.47(18) . . ? F2 C26 C1 109.31(17) . . ? F1 C26 C34 112.56(17) . . ? F2 C26 C34 109.02(18) . . ? C1 C26 C34 104.16(15) . . ? N4 C27 C31 123.1(2) . . ? N4 C27 C17 115.60(18) . . ? C31 C27 C17 121.32(19) . . ? C42 C28 C33 122.51(18) . . ? C42 C28 N1 118.59(17) . . ? C33 C28 N1 118.89(19) . . ? C33 C29 C12 120.27(17) . . ? O9 C30 C41 107.12(17) . . ? C43 C31 C27 118.4(2) . . ? C50 N4 C27 117.1(2) . . ? C50 N4 Ag1 129.92(18) . . ? C27 N4 Ag1 111.97(14) . . ? C28 C33 C29 118.61(19) . . ? F4 C34 F6 107.32(16) . . ? F4 C34 C20 112.15(16) . . ? F6 C34 C20 113.75(16) . . ? F4 C34 C26 109.01(16) . . ? F6 C34 C26 110.10(16) . . ? C20 C34 C26 104.45(15) . . ? C42 C35 C12 120.4(2) . . ? O39 N1 O37 123.52(19) . . ? O39 N1 C28 118.1(2) . . ? O37 N1 C28 118.40(17) . . ? C28 C42 C35 118.61(18) . . ? C44 C43 C31 119.2(2) . . ? C43 C44 C50 118.5(2) . . ? N4 C50 C44 123.7(2) . . ? O23 S3 O23 178.4(3) 2_556 . ? O23 S3 O21 65.2(2) 2_556 . ? O23 S3 O21 113.4(2) . . ? O23 S3 O21 113.4(2) 2_556 2_556 ? O23 S3 O21 65.2(2) . 2_556 ? O21 S3 O21 77.7(2) . 2_556 ? O23 S3 O22 113.2(2) 2_556 2_556 ? O23 S3 O22 68.14(19) . 2_556 ? O21 S3 O22 176.27(16) . 2_556 ? O21 S3 O22 100.26(15) 2_556 2_556 ? O23 S3 O22 68.14(19) 2_556 . ? O23 S3 O22 113.2(2) . . ? O21 S3 O22 100.26(15) . . ? O21 S3 O22 176.27(16) 2_556 . ? O22 S3 O22 81.9(2) 2_556 . ? O23 S3 C66 63.3(2) 2_556 2_556 ? O23 S3 C66 116.7(2) . 2_556 ? O21 S3 C66 105.72(18) . 2_556 ? O21 S3 C66 77.66(18) 2_556 2_556 ? O22 S3 C66 70.69(17) 2_556 2_556 ? O22 S3 C66 105.97(17) . 2_556 ? O23 S3 C66 116.7(2) 2_556 . ? O23 S3 C66 63.3(2) . . ? O21 S3 C66 77.66(18) . . ? O21 S3 C66 105.72(18) 2_556 . ? O22 S3 C66 105.97(17) 2_556 . ? O22 S3 C66 70.69(17) . . ? C66 S3 C66 175.8(3) 2_556 . ? C66 F22 O22 80.5(2) . . ? C66 F23 O23 62.8(2) . . ? F23 C66 F22 107.9(3) . . ? F23 C66 F21 107.4(3) . . ? F22 C66 F21 107.1(3) . . ? F23 C66 O23 69.8(2) . . ? F22 C66 O23 132.5(3) . . ? F21 C66 O23 119.0(3) . . ? F23 C66 S3 117.7(3) . . ? F22 C66 S3 107.4(3) . . ? F21 C66 S3 108.9(3) . . ? O23 C66 S3 48.54(17) . . ? F23 C66 O22 129.2(3) . . ? F22 C66 O22 54.9(2) . . ? F21 C66 O22 123.1(3) . . ? O23 C66 O22 88.8(2) . . ? S3 C66 O22 52.52(15) . . ? S3 O21 O23 50.24(15) . 2_556 ? S3 O21 Ag1 117.43(15) . . ? O23 O21 Ag1 131.9(2) 2_556 . ? F22 O22 S3 101.34(19) . . ? F22 O22 O23 126.7(2) . 2_556 ? S3 O22 O23 49.17(14) . 2_556 ? F22 O22 C66 44.58(17) . . ? S3 O22 C66 56.79(15) . . ? O23 O22 C66 93.2(2) 2_556 . ? S3 O23 O21 64.52(19) . 2_556 ? S3 O23 C66 68.1(2) . . ? O21 O23 C66 108.3(3) 2_556 . ? S3 O23 O22 62.69(17) . 2_556 ? O21 O23 O22 96.9(2) 2_556 2_556 ? C66 O23 O22 105.6(3) . 2_556 ? S3 O23 F23 114.9(2) . . ? O21 O23 F23 137.0(3) 2_556 . ? C66 O23 F23 47.4(2) . . ? O22 O23 F23 121.8(3) 2_556 . ? _diffrn_measured_fraction_theta_max 0.816 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.991 _refine_diff_density_min -0.880 _refine_diff_density_rms 0.083 data_2a _database_code_depnum_ccdc_archive 'CCDC 633205' _audit_creation_method SHELXL-97 _chemical_name_systematic 1,2-bis[5-ethoxy-2-(4-nitro-phenyl)thiazoyl]perfluorocyclopentene _chemical_name_common ;1,2-bis(5-ethoxy-2-(4-nitro- phenyl)thiazoyl)perfluorocyclopentene ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H18 F6 N4 O6 S2' _chemical_formula_sum 'C27 H18 F6 N4 O6 S2' _chemical_formula_weight 672.59 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 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 16.5004(7) _cell_length_b 11.8425(5) _cell_length_c 14.1320(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.387(2) _cell_angle_gamma 90.00 _cell_volume 2731.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 6808 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 29.51 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'X8 ApexII Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17437 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.02 _reflns_number_total 6535 _reflns_number_gt 4819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1425P)^2^+2.4306P] 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_number_reflns 6535 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0717 _refine_ls_wR_factor_ref 0.2089 _refine_ls_wR_factor_gt 0.1873 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.015 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 F1 F 0.12428(11) -0.02240(15) 0.29701(16) 0.0319(5) Uani 1 1 d . . . F2 F 0.23542(14) -0.04043(15) 0.39949(12) 0.0345(5) Uani 1 1 d . . . S1 S 0.20108(4) 0.38809(5) 0.44088(4) 0.01192(19) Uani 1 1 d . . . S2 S 0.31307(4) 0.38706(5) 0.06938(4) 0.01180(18) Uani 1 1 d . . . F4 F 0.18587(11) -0.10191(16) 0.16042(13) 0.0299(5) Uani 1 1 d . . . O4 O 0.18944(11) 0.32113(15) 0.16341(13) 0.0128(4) Uani 1 1 d . . . F5 F 0.31834(12) -0.02904(14) 0.11112(12) 0.0268(4) Uani 1 1 d . . . O3 O 0.32484(11) 0.32311(15) 0.34662(13) 0.0131(4) Uani 1 1 d . . . F3 F 0.27187(12) -0.17996(14) 0.27232(14) 0.0305(5) Uani 1 1 d . . . N3 N 0.38324(14) 0.20111(18) 0.13203(15) 0.0128(5) Uani 1 1 d . . . F6 F 0.38431(10) -0.03142(14) 0.25510(14) 0.0261(4) Uani 1 1 d . . . N2 N 0.13223(14) 0.20074(18) 0.38032(15) 0.0121(4) Uani 1 1 d . . . O6 O 0.64112(14) 0.37912(18) -0.21557(15) 0.0223(5) Uani 1 1 d . . . O5 O 0.72812(12) 0.32932(18) -0.09300(15) 0.0221(5) Uani 1 1 d . . . O1 O -0.21787(13) 0.33739(18) 0.59040(17) 0.0248(5) Uani 1 1 d . . . C9 C 0.25115(16) 0.3012(2) 0.36989(18) 0.0107(5) Uani 1 1 d . . . C22 C 0.46312(17) 0.3083(2) 0.02796(18) 0.0130(5) Uani 1 1 d . . . C18 C 0.26316(16) 0.3010(2) 0.14066(17) 0.0112(5) Uani 1 1 d . . . O2 O -0.13345(15) 0.3682(2) 0.72045(17) 0.0324(6) Uani 1 1 d . . . C26 C 0.51523(17) 0.3820(2) -0.11064(19) 0.0144(5) Uani 1 1 d . . . H26 H 0.5077 0.4215 -0.1681 0.017 Uiso 1 1 calc R . . C8 C 0.20516(16) 0.2055(2) 0.34353(17) 0.0105(5) Uani 1 1 d . . . C12 C 0.23081(16) 0.1125(2) 0.28845(18) 0.0109(5) Uani 1 1 d . . . N4 N 0.65790(14) 0.34772(19) -0.13235(17) 0.0141(5) Uani 1 1 d . . . C7 C 0.12178(16) 0.2895(2) 0.43180(18) 0.0126(5) Uani 1 1 d . . . C4 C 0.05131(17) 0.3076(2) 0.48197(19) 0.0133(5) Uani 1 1 d . . . C21 C 0.39366(16) 0.2890(2) 0.08005(18) 0.0126(5) Uani 1 1 d . . . C17 C 0.30976(16) 0.2059(2) 0.16788(17) 0.0113(5) Uani 1 1 d . . . C6 C -0.08998(17) 0.2714(2) 0.4976(2) 0.0170(6) Uani 1 1 d . . . H6 H -0.1406 0.2395 0.4748 0.020 Uiso 1 1 calc R . . C25 C 0.59046(16) 0.3345(2) -0.07567(19) 0.0131(5) Uani 1 1 d . . . C24 C 0.60503(17) 0.2766(2) 0.0106(2) 0.0170(6) Uani 1 1 d . . . H24 H 0.6567 0.2476 0.0330 0.020 Uiso 1 1 calc R . . C2 C -0.00544(18) 0.3849(2) 0.6169(2) 0.0168(6) Uani 1 1 d . . . H2 H 0.0001 0.4264 0.6733 0.020 Uiso 1 1 calc R . . C16 C 0.28310(16) 0.1123(2) 0.22149(18) 0.0109(5) Uani 1 1 d . . . C11 C 0.44785(17) 0.4298(2) 0.3498(2) 0.0178(6) Uani 1 1 d . . . H11A H 0.4766 0.4971 0.3729 0.027 Uiso 1 1 calc R . . H11B H 0.4405 0.4291 0.2812 0.027 Uiso 1 1 calc R . . H11C H 0.4790 0.3647 0.3739 0.027 Uiso 1 1 calc R . . C23 C 0.54028(17) 0.2631(2) 0.06245(19) 0.0167(6) Uani 1 1 d . . . H23 H 0.5482 0.2239 0.1201 0.020 Uiso 1 1 calc R . . C5 C -0.02409(17) 0.2578(2) 0.44835(19) 0.0168(6) Uani 1 1 d . . . H5 H -0.0300 0.2151 0.3925 0.020 Uiso 1 1 calc R . . C15 C 0.30912(17) -0.0067(2) 0.20263(19) 0.0137(5) Uani 1 1 d . . . N1 N -0.14849(15) 0.3467(2) 0.63494(18) 0.0183(5) Uani 1 1 d . . . C3 C 0.05973(17) 0.3728(2) 0.56618(19) 0.0152(5) Uani 1 1 d . . . H3 H 0.1094 0.4079 0.5879 0.018 Uiso 1 1 calc R . . C13 C 0.20553(17) -0.0070(2) 0.30896(18) 0.0143(5) Uani 1 1 d . . . C27 C 0.45221(17) 0.3691(2) -0.05807(19) 0.0141(5) Uani 1 1 d . . . H27 H 0.4015 0.4013 -0.0798 0.017 Uiso 1 1 calc R . . C19 C 0.14778(17) 0.4245(2) 0.12668(19) 0.0154(5) Uani 1 1 d . . . H19A H 0.1417 0.4260 0.0574 0.019 Uiso 1 1 calc R . . H19B H 0.1790 0.4903 0.1513 0.019 Uiso 1 1 calc R . . C20 C 0.06484(17) 0.4244(2) 0.1597(2) 0.0198(6) Uani 1 1 d . . . H20A H 0.0353 0.4912 0.1369 0.030 Uiso 1 1 calc R . . H20B H 0.0717 0.4230 0.2283 0.030 Uiso 1 1 calc R . . H20C H 0.0347 0.3589 0.1350 0.030 Uiso 1 1 calc R . . C1 C -0.07904(17) 0.3336(2) 0.5816(2) 0.0150(5) Uani 1 1 d . . . C10 C 0.36571(17) 0.4272(2) 0.38348(19) 0.0150(5) Uani 1 1 d . . . H10A H 0.3723 0.4282 0.4528 0.018 Uiso 1 1 calc R . . H10B H 0.3336 0.4925 0.3595 0.018 Uiso 1 1 calc R . . C14 C 0.24449(17) -0.0816(2) 0.2378(2) 0.0191(6) 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 F1 0.0203(10) 0.0223(9) 0.0562(14) -0.0066(9) 0.0160(9) -0.0077(7) F2 0.0712(15) 0.0183(9) 0.0130(8) 0.0022(7) 0.0021(9) -0.0082(9) S1 0.0149(4) 0.0109(3) 0.0110(3) -0.0017(2) 0.0053(2) -0.0007(2) S2 0.0156(4) 0.0102(3) 0.0107(3) 0.0017(2) 0.0052(2) 0.0011(2) F4 0.0287(11) 0.0355(11) 0.0240(10) -0.0093(8) -0.0016(8) -0.0066(8) O4 0.0131(10) 0.0119(9) 0.0145(9) 0.0030(7) 0.0056(7) 0.0027(7) F5 0.0464(12) 0.0190(8) 0.0167(8) -0.0030(7) 0.0098(8) 0.0030(8) O3 0.0132(10) 0.0131(9) 0.0142(9) -0.0025(7) 0.0055(7) -0.0024(7) F3 0.0440(12) 0.0135(8) 0.0363(11) 0.0038(7) 0.0141(9) 0.0023(8) N3 0.0162(12) 0.0122(10) 0.0105(10) -0.0008(8) 0.0037(8) -0.0003(8) F6 0.0167(9) 0.0195(8) 0.0409(11) -0.0022(8) -0.0002(8) 0.0040(7) N2 0.0141(12) 0.0126(10) 0.0104(10) 0.0012(8) 0.0041(8) -0.0003(8) O6 0.0242(12) 0.0258(11) 0.0193(11) 0.0073(8) 0.0108(9) 0.0070(8) O5 0.0139(11) 0.0283(11) 0.0252(11) 0.0025(9) 0.0063(9) 0.0023(8) O1 0.0155(11) 0.0262(11) 0.0336(13) -0.0013(9) 0.0068(9) -0.0021(8) C9 0.0117(13) 0.0115(11) 0.0096(11) 0.0010(9) 0.0043(9) 0.0008(9) C22 0.0168(14) 0.0115(11) 0.0116(12) -0.0021(9) 0.0053(10) -0.0009(10) C18 0.0156(13) 0.0098(11) 0.0087(11) -0.0021(9) 0.0027(10) -0.0014(9) O2 0.0276(13) 0.0450(14) 0.0279(13) -0.0155(11) 0.0156(10) -0.0118(11) C26 0.0183(14) 0.0134(12) 0.0118(12) 0.0028(9) 0.0034(10) -0.0004(10) C8 0.0136(13) 0.0098(11) 0.0087(11) 0.0000(9) 0.0040(9) -0.0012(9) C12 0.0135(13) 0.0094(11) 0.0095(11) 0.0010(9) 0.0007(10) -0.0032(9) N4 0.0159(12) 0.0112(10) 0.0165(11) -0.0006(8) 0.0063(9) 0.0012(8) C7 0.0153(14) 0.0128(11) 0.0097(11) 0.0004(9) 0.0020(10) -0.0004(9) C4 0.0150(14) 0.0137(12) 0.0118(12) 0.0013(9) 0.0041(10) 0.0015(10) C21 0.0150(13) 0.0126(11) 0.0103(11) -0.0016(9) 0.0025(10) -0.0002(10) C17 0.0148(13) 0.0116(11) 0.0085(11) -0.0003(9) 0.0053(10) -0.0001(9) C6 0.0126(14) 0.0205(13) 0.0177(13) -0.0004(11) 0.0019(10) -0.0028(10) C25 0.0140(14) 0.0121(11) 0.0146(12) -0.0012(10) 0.0065(10) -0.0017(9) C24 0.0162(14) 0.0179(13) 0.0169(13) 0.0019(10) 0.0021(10) 0.0039(10) C2 0.0202(15) 0.0166(13) 0.0148(13) -0.0048(10) 0.0059(11) -0.0011(10) C16 0.0126(13) 0.0099(11) 0.0097(11) -0.0012(9) 0.0003(10) 0.0011(9) C11 0.0158(14) 0.0155(12) 0.0231(14) 0.0025(11) 0.0057(11) -0.0023(10) C23 0.0197(15) 0.0184(13) 0.0124(12) 0.0039(10) 0.0036(10) 0.0007(11) C5 0.0189(15) 0.0176(12) 0.0138(12) -0.0029(10) 0.0026(10) -0.0014(10) C15 0.0176(14) 0.0111(11) 0.0129(12) 0.0003(9) 0.0043(10) 0.0011(10) N1 0.0180(13) 0.0148(11) 0.0243(13) -0.0049(9) 0.0105(10) -0.0040(9) C3 0.0145(14) 0.0171(13) 0.0142(12) -0.0027(10) 0.0023(10) -0.0015(10) C13 0.0203(14) 0.0118(12) 0.0114(12) 0.0000(9) 0.0043(10) -0.0033(10) C27 0.0137(14) 0.0148(12) 0.0141(12) 0.0019(10) 0.0026(10) 0.0010(10) C19 0.0210(15) 0.0099(11) 0.0160(13) 0.0017(10) 0.0045(11) 0.0060(10) C20 0.0166(15) 0.0185(13) 0.0253(15) -0.0038(11) 0.0064(12) 0.0014(11) C1 0.0150(14) 0.0133(12) 0.0181(13) 0.0007(10) 0.0070(11) 0.0005(10) C10 0.0185(14) 0.0120(12) 0.0153(12) -0.0023(10) 0.0054(10) -0.0038(10) C14 0.0205(16) 0.0115(12) 0.0262(15) -0.0015(10) 0.0059(12) -0.0023(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 F1 C13 1.339(3) . ? F2 C13 1.361(3) . ? S1 C9 1.729(3) . ? S1 C7 1.745(3) . ? S2 C18 1.725(3) . ? S2 C21 1.755(3) . ? F4 C14 1.372(3) . ? O4 C18 1.324(3) . ? O4 C19 1.462(3) . ? F5 C15 1.350(3) . ? O3 C9 1.331(3) . ? O3 C10 1.464(3) . ? F3 C14 1.317(3) . ? N3 C21 1.300(3) . ? N3 C17 1.382(3) . ? F6 C15 1.381(3) . ? N2 C7 1.304(3) . ? N2 C8 1.380(3) . ? O6 N4 1.226(3) . ? O5 N4 1.229(3) . ? O1 N1 1.228(3) . ? C9 C8 1.385(3) . ? C22 C23 1.401(4) . ? C22 C27 1.402(4) . ? C22 C21 1.468(4) . ? C18 C17 1.386(3) . ? O2 N1 1.224(3) . ? C26 C27 1.372(4) . ? C26 C25 1.386(4) . ? C8 C12 1.447(3) . ? C12 C16 1.370(4) . ? C12 C13 1.515(3) . ? N4 C25 1.471(3) . ? C7 C4 1.463(4) . ? C4 C5 1.396(4) . ? C4 C3 1.408(4) . ? C17 C16 1.447(3) . ? C6 C5 1.383(4) . ? C6 C1 1.385(4) . ? C25 C24 1.389(4) . ? C24 C23 1.390(4) . ? C2 C3 1.384(4) . ? C2 C1 1.384(4) . ? C16 C15 1.508(3) . ? C11 C10 1.501(4) . ? C15 C14 1.525(4) . ? N1 C1 1.469(3) . ? C13 C14 1.547(4) . ? C19 C20 1.509(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 C9 S1 C7 88.61(12) . . ? C18 S2 C21 88.80(12) . . ? C18 O4 C19 117.8(2) . . ? C9 O3 C10 117.8(2) . . ? C21 N3 C17 111.7(2) . . ? C7 N2 C8 111.8(2) . . ? O3 C9 C8 125.3(2) . . ? O3 C9 S1 123.98(19) . . ? C8 C9 S1 110.72(19) . . ? C23 C22 C27 119.6(2) . . ? C23 C22 C21 120.2(2) . . ? C27 C22 C21 120.3(2) . . ? O4 C18 C17 124.8(2) . . ? O4 C18 S2 124.69(19) . . ? C17 C18 S2 110.45(19) . . ? C27 C26 C25 118.2(2) . . ? N2 C8 C9 114.0(2) . . ? N2 C8 C12 120.7(2) . . ? C9 C8 C12 125.2(2) . . ? C16 C12 C8 129.4(2) . . ? C16 C12 C13 110.4(2) . . ? C8 C12 C13 119.9(2) . . ? O6 N4 O5 123.6(2) . . ? O6 N4 C25 118.1(2) . . ? O5 N4 C25 118.2(2) . . ? N2 C7 C4 124.6(2) . . ? N2 C7 S1 114.9(2) . . ? C4 C7 S1 120.43(19) . . ? C5 C4 C3 119.5(2) . . ? C5 C4 C7 120.3(2) . . ? C3 C4 C7 120.2(2) . . ? N3 C21 C22 125.8(2) . . ? N3 C21 S2 114.7(2) . . ? C22 C21 S2 119.43(19) . . ? N3 C17 C18 114.4(2) . . ? N3 C17 C16 120.7(2) . . ? C18 C17 C16 124.7(2) . . ? C5 C6 C1 118.6(3) . . ? C26 C25 C24 123.0(3) . . ? C26 C25 N4 118.2(2) . . ? C24 C25 N4 118.8(2) . . ? C23 C24 C25 118.1(3) . . ? C3 C2 C1 118.3(2) . . ? C12 C16 C17 129.1(2) . . ? C12 C16 C15 110.3(2) . . ? C17 C16 C15 120.5(2) . . ? C24 C23 C22 120.1(2) . . ? C6 C5 C4 120.4(3) . . ? F5 C15 F6 104.8(2) . . ? F5 C15 C16 115.3(2) . . ? F6 C15 C16 111.1(2) . . ? F5 C15 C14 112.3(2) . . ? F6 C15 C14 108.5(2) . . ? C16 C15 C14 104.8(2) . . ? O2 N1 O1 124.3(2) . . ? O2 N1 C1 117.9(2) . . ? O1 N1 C1 117.8(2) . . ? C2 C3 C4 120.4(3) . . ? F1 C13 F2 107.3(2) . . ? F1 C13 C12 113.7(2) . . ? F2 C13 C12 112.3(2) . . ? F1 C13 C14 110.1(2) . . ? F2 C13 C14 108.5(2) . . ? C12 C13 C14 104.9(2) . . ? C26 C27 C22 121.0(3) . . ? O4 C19 C20 106.9(2) . . ? C2 C1 C6 122.7(3) . . ? C2 C1 N1 118.5(2) . . ? C6 C1 N1 118.8(2) . . ? O3 C10 C11 107.1(2) . . ? F3 C14 F4 107.7(2) . . ? F3 C14 C15 114.6(2) . . ? F4 C14 C15 106.7(2) . . ? F3 C14 C13 114.7(2) . . ? F4 C14 C13 107.9(2) . . ? C15 C14 C13 104.8(2) . . ? _diffrn_measured_fraction_theta_max 0.820 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.965 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.150