# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof C Drain' _publ_contact_author_email CDRAIN@HUNTER.CUNY.EDU _publ_section_title ; Self-organization of a new fluorous porphyrin and C60 films on indium-tin-oxide electrode ; loop_ _publ_author_name 'C. Drain' 'Jessica Koehne' 'Gang-yu Liu.' 'Louis Todaro' 'Alessandro Varotto' 'Mikki Vinodu' # Attachment 'TPPF100_cif_July_17_2008.file.cif' data_x1611l _database_code_depnum_ccdc_archive 'CCDC 670308' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C104 H50 F100 N4 O4 S4' _chemical_formula_weight 3447.72 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3570(19) _cell_length_b 10.938(2) _cell_length_c 30.832(6) _cell_angle_alpha 87.69(3) _cell_angle_beta 88.34(3) _cell_angle_gamma 77.12(3) _cell_volume 3073.1(11) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12247 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.56 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1698 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9455 _exptl_absorpt_correction_T_max 0.9777 _exptl_absorpt_process_details numerical _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25263 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.1152 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.56 _reflns_number_total 12247 _reflns_number_gt 6936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+12.8529P] 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 12247 _refine_ls_number_parameters 973 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1858 _refine_ls_R_factor_gt 0.1011 _refine_ls_wR_factor_ref 0.1913 _refine_ls_wR_factor_gt 0.1581 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.2458(2) 0.7897(2) 0.33431(7) 0.0610(6) Uani 1 1 d . . . S2 S 0.35924(19) 0.02961(18) 0.25960(5) 0.0396(5) Uani 1 1 d . . . F22 F 1.0688(4) 0.5543(4) 0.46232(12) 0.0464(10) Uani 1 1 d . . . F23 F 1.2758(4) 0.6337(4) 0.41684(14) 0.0549(12) Uani 1 1 d . . . F25 F 0.9340(5) 0.8019(4) 0.30807(12) 0.0551(12) Uani 1 1 d . . . F26 F 0.7267(4) 0.7217(4) 0.35432(11) 0.0431(10) Uani 1 1 d . . . F32 F 0.5591(4) 0.0526(4) 0.41080(11) 0.0428(10) Uani 1 1 d . . . F33 F 0.5239(4) -0.0710(4) 0.34074(12) 0.0470(10) Uani 1 1 d . . . F35 F 0.2470(4) 0.3017(4) 0.27642(11) 0.0463(10) Uani 1 1 d . . . F36 F 0.2755(4) 0.4233(4) 0.34749(12) 0.0497(11) Uani 1 1 d . . . F63B F 1.5200(4) 0.4690(4) 0.25481(13) 0.0506(11) Uani 1 1 d . . . F63A F 1.4769(4) 0.6326(4) 0.21157(11) 0.0514(11) Uani 1 1 d . . . F64B F 1.7751(4) 0.5129(4) 0.27727(11) 0.0485(11) Uani 1 1 d . . . F64A F 1.7274(4) 0.6974(4) 0.24509(12) 0.0473(11) Uani 1 1 d . . . F65A F 1.7381(4) 0.4168(4) 0.19436(11) 0.0407(10) Uani 1 1 d . . . F65B F 1.7360(4) 0.6048(4) 0.16803(11) 0.0426(10) Uani 1 1 d . . . F66A F 1.9937(4) 0.5878(4) 0.22084(11) 0.0448(10) Uani 1 1 d . . . F66B F 1.9978(4) 0.3874(4) 0.22543(12) 0.0505(11) Uani 1 1 d . . . F67A F 2.0079(4) 0.5887(4) 0.13560(11) 0.0383(9) Uani 1 1 d . . . F67B F 1.9613(4) 0.4024(4) 0.13367(11) 0.0416(10) Uani 1 1 d . . . F68A F 2.2123(4) 0.2922(4) 0.16584(12) 0.0442(10) Uani 1 1 d . . . F68B F 2.2513(4) 0.4650(4) 0.19039(11) 0.0449(10) Uani 1 1 d . . . F69A F 2.2000(4) 0.4167(4) 0.08139(11) 0.0432(10) Uani 1 1 d . . . F69B F 2.2900(4) 0.5579(4) 0.11271(12) 0.0434(10) Uani 1 1 d . . . F70A F 2.4985(4) 0.3448(4) 0.15095(11) 0.0380(9) Uani 1 1 d . . . F70B F 2.4232(4) 0.2369(4) 0.10185(11) 0.0395(9) Uani 1 1 d . . . F71A F 2.5768(4) 0.5000(4) 0.09411(12) 0.0424(10) Uani 1 1 d . . . F71B F 2.4583(4) 0.4388(4) 0.04175(11) 0.0441(10) Uani 1 1 d . . . F72A F 2.7513(4) 0.3641(4) 0.03614(13) 0.0566(12) Uani 1 1 d . . . F72B F 2.7596(4) 0.2680(4) 0.09879(12) 0.0478(10) Uani 1 1 d . . . F72C F 2.6480(4) 0.2080(4) 0.04623(12) 0.0497(11) Uani 1 1 d . . . F83A F 0.6763(4) 0.0694(4) 0.14946(10) 0.0377(9) Uani 1 1 d . . . F83B F 0.7623(4) 0.1592(4) 0.20144(12) 0.0427(10) Uani 1 1 d . . . F84A F 0.9601(4) -0.0575(4) 0.22051(11) 0.0432(10) Uani 1 1 d . . . F84B F 0.8614(4) -0.1555(4) 0.17290(12) 0.0455(10) Uani 1 1 d . . . F85A F 0.9974(4) 0.1128(4) 0.15099(12) 0.0444(10) Uani 1 1 d . . . F85B F 0.9312(4) -0.0160(4) 0.10788(11) 0.0448(10) Uani 1 1 d . . . F86A F 1.1449(4) -0.2088(4) 0.15500(12) 0.0439(10) Uani 1 1 d . . . F86B F 1.2243(4) -0.0505(4) 0.17763(11) 0.0438(10) Uani 1 1 d . . . F87A F 1.2074(4) 0.0405(4) 0.08856(11) 0.0431(10) Uani 1 1 d . . . F87B F 1.1810(4) -0.1462(4) 0.07323(11) 0.0435(10) Uani 1 1 d . . . F88A F 1.4588(4) -0.0441(4) 0.12312(11) 0.0427(10) Uani 1 1 d . . . F88B F 1.4280(4) -0.2357(4) 0.13049(11) 0.0417(10) Uani 1 1 d . . . F89A F 1.4200(4) -0.0687(4) 0.03141(11) 0.0387(9) Uani 1 1 d . . . F89B F 1.4505(4) -0.2700(3) 0.04720(11) 0.0361(9) Uani 1 1 d . . . F90A F 1.6995(4) -0.2369(4) 0.09687(11) 0.0457(10) Uani 1 1 d . . . F90B F 1.6730(4) -0.0585(4) 0.06059(11) 0.0442(10) Uani 1 1 d . . . F91A F 1.6576(4) -0.1968(4) -0.01520(11) 0.0418(10) Uani 1 1 d . . . F91B F 1.7303(4) -0.3656(4) 0.02582(12) 0.0471(10) Uani 1 1 d . . . F92A F 1.8990(4) -0.1148(4) 0.00540(13) 0.0575(12) Uani 1 1 d . . . F92B F 1.9484(5) -0.3019(5) -0.01784(14) 0.0683(14) Uani 1 1 d . . . F92C F 1.9650(4) -0.2716(5) 0.05018(13) 0.0618(13) Uani 1 1 d . . . N1 N 0.6408(5) 0.6213(5) 0.50766(14) 0.0280(12) Uani 1 1 d . . . H1A H 0.5855 0.5672 0.5042 0.034 Uiso 0.50 1 calc PR . . N2 N 0.5893(5) 0.4649(5) 0.43958(15) 0.0288(12) Uani 1 1 d . . . H2A H 0.5480 0.4853 0.4651 0.035 Uiso 0.50 1 calc PR . . C1 C 0.6427(7) 0.6894(6) 0.54376(19) 0.0320(15) Uani 1 1 d . . . C2 C 0.7472(7) 0.7663(6) 0.53618(19) 0.0346(16) Uani 1 1 d . . . H2B H 0.7718 0.8223 0.5560 0.042 Uiso 1 1 calc R . . C3 C 0.8044(7) 0.7449(6) 0.49577(19) 0.0349(16) Uani 1 1 d . . . H3A H 0.8748 0.7847 0.4819 0.042 Uiso 1 1 calc R . . C4 C 0.7408(6) 0.6520(6) 0.47748(18) 0.0289(15) Uani 1 1 d . . . C5 C 0.7731(6) 0.5954(6) 0.43740(17) 0.0276(14) Uani 1 1 d . . . C6 C 0.7043(6) 0.5082(6) 0.42057(19) 0.0308(15) Uani 1 1 d . . . C7 C 0.7394(7) 0.4516(6) 0.37908(19) 0.0338(16) Uani 1 1 d . . . H7A H 0.8146 0.4650 0.3593 0.041 Uiso 1 1 calc R . . C8 C 0.6471(7) 0.3771(6) 0.37353(19) 0.0336(16) Uani 1 1 d . . . H8A H 0.6443 0.3279 0.3490 0.040 Uiso 1 1 calc R . . C9 C 0.5513(7) 0.3846(6) 0.41175(18) 0.0290(14) Uani 1 1 d . . . C10 C 0.4441(7) 0.3163(6) 0.41882(19) 0.0307(15) Uani 1 1 d . . . C21 C 0.8897(7) 0.6364(6) 0.41034(18) 0.0306(15) Uani 1 1 d . . . C22 C 1.0312(7) 0.6173(7) 0.4241(2) 0.0373(17) Uani 1 1 d . . . C23 C 1.1401(7) 0.6577(7) 0.3999(2) 0.0401(18) Uani 1 1 d . . . C24 C 1.1123(7) 0.7213(6) 0.3611(2) 0.0377(17) Uani 1 1 d . . . C25 C 0.9702(8) 0.7407(7) 0.3460(2) 0.0418(18) Uani 1 1 d . . . C26 C 0.8613(7) 0.6994(6) 0.37020(19) 0.0339(16) Uani 1 1 d . . . C31 C 0.4183(6) 0.2403(6) 0.38149(18) 0.0298(15) Uani 1 1 d . . . C32 C 0.4772(7) 0.1152(6) 0.37826(19) 0.0291(15) Uani 1 1 d . . . C33 C 0.4600(7) 0.0505(6) 0.3423(2) 0.0322(15) Uani 1 1 d . . . C34 C 0.3832(7) 0.1114(7) 0.30658(19) 0.0336(16) Uani 1 1 d . . . C35 C 0.3233(7) 0.2350(7) 0.3098(2) 0.0350(16) Uani 1 1 d . . . C36 C 0.3380(7) 0.2998(7) 0.3457(2) 0.0343(16) Uani 1 1 d . . . C61 C 1.3095(7) 0.6835(7) 0.2904(2) 0.048(2) Uani 1 1 d . . . H61A H 1.2823 0.6021 0.2967 0.057 Uiso 1 1 calc R . . H61B H 1.2639 0.7197 0.2629 0.057 Uiso 1 1 calc R . . C62 C 1.4741(7) 0.6646(7) 0.2866(2) 0.0389(17) Uani 1 1 d . . . H62A H 1.4992 0.7478 0.2832 0.047 Uiso 1 1 calc R . . H62B H 1.5175 0.6242 0.3139 0.047 Uiso 1 1 calc R . . C63 C 1.5415(7) 0.5869(7) 0.2497(2) 0.0374(17) Uani 1 1 d . . . C64 C 1.7059(7) 0.5798(6) 0.2432(2) 0.0342(16) Uani 1 1 d . . . C65 C 1.7813(7) 0.5228(6) 0.20146(19) 0.0311(15) Uani 1 1 d . . . C66 C 1.9505(7) 0.4941(7) 0.20165(19) 0.0344(16) Uani 1 1 d . . . C67 C 2.0263(7) 0.4762(7) 0.15602(19) 0.0339(16) Uani 1 1 d . . . C68 C 2.1933(7) 0.4161(7) 0.1577(2) 0.0339(16) Uani 1 1 d . . . C69 C 2.2786(7) 0.4377(6) 0.1152(2) 0.0330(16) Uani 1 1 d . . . C70 C 2.4354(7) 0.3514(7) 0.1119(2) 0.0328(16) Uani 1 1 d . . . C71 C 2.5359(7) 0.4005(6) 0.0776(2) 0.0316(15) Uani 1 1 d . . . C72 C 2.6763(7) 0.3070(7) 0.0649(2) 0.0348(16) Uani 1 1 d . . . C81 C 0.4851(7) 0.0868(7) 0.2217(2) 0.0389(17) Uani 1 1 d . . . H81A H 0.4449 0.0940 0.1921 0.047 Uiso 1 1 calc R . . H81B H 0.4932 0.1715 0.2299 0.047 Uiso 1 1 calc R . . C82 C 0.6365(7) 0.0002(6) 0.22136(19) 0.0358(16) Uani 1 1 d . . . H82A H 0.6780 -0.0054 0.2507 0.043 Uiso 1 1 calc R . . H82B H 0.6284 -0.0850 0.2137 0.043 Uiso 1 1 calc R . . C83 C 0.7386(7) 0.0473(6) 0.18903(18) 0.0302(15) Uani 1 1 d . . . C84 C 0.8868(7) -0.0433(6) 0.18285(19) 0.0327(16) Uani 1 1 d . . . C85 C 0.9896(7) -0.0063(6) 0.14650(19) 0.0326(16) Uani 1 1 d . . . C86 C 1.1490(7) -0.0891(7) 0.14622(19) 0.0342(16) Uani 1 1 d . . . C87 C 1.2321(7) -0.0793(7) 0.10236(19) 0.0346(16) Uani 1 1 d . . . C88 C 1.4013(7) -0.1311(6) 0.10498(18) 0.0286(14) Uani 1 1 d . . . C89 C 1.4785(7) -0.1623(6) 0.0600(2) 0.0318(15) Uani 1 1 d . . . C90 C 1.6453(7) -0.1728(6) 0.06009(19) 0.0337(16) Uani 1 1 d . . . C91 C 1.7304(7) -0.2435(7) 0.0219(2) 0.0378(17) Uani 1 1 d . . . C92 C 1.8883(7) -0.2309(8) 0.0144(2) 0.0454(19) Uani 1 1 d . . . O101 O 1.1013(7) 0.9064(7) 0.45056(19) 0.099(3) Uani 1 1 d . . . C101 C 1.2061(10) 0.8727(8) 0.4740(3) 0.065(2) Uani 1 1 d . . . C102 C 1.1862(10) 0.8304(9) 0.5196(3) 0.076(3) Uani 1 1 d . . . H10A H 1.0815 0.8374 0.5260 0.114 Uiso 1 1 calc R . . H10B H 1.2251 0.8830 0.5391 0.114 Uiso 1 1 calc R . . H10C H 1.2387 0.7427 0.5237 0.114 Uiso 1 1 calc R . . C103 C 1.3584(11) 0.8684(9) 0.4588(3) 0.080(3) Uani 1 1 d . . . H10D H 1.3583 0.8987 0.4285 0.120 Uiso 1 1 calc R . . H10E H 1.4158 0.7818 0.4611 0.120 Uiso 1 1 calc R . . H10F H 1.4022 0.9217 0.4768 0.120 Uiso 1 1 calc R . . O201 O 0.7522(6) 0.0907(6) 0.31869(19) 0.0748(19) Uani 1 1 d . . . C201 C 0.8699(9) 0.1097(7) 0.3263(2) 0.049(2) Uani 1 1 d . . . C202 C 0.9459(9) 0.1808(9) 0.2947(2) 0.067(3) Uani 1 1 d . . . H20A H 0.8878 0.2015 0.2684 0.100 Uiso 1 1 calc R . . H20B H 1.0427 0.1295 0.2872 0.100 Uiso 1 1 calc R . . H20C H 0.9574 0.2583 0.3076 0.100 Uiso 1 1 calc R . . C203 C 0.9448(13) 0.0718(10) 0.3680(3) 0.103(4) Uani 1 1 d . . . H20D H 0.8860 0.0259 0.3865 0.155 Uiso 1 1 calc R . . H20E H 0.9561 0.1468 0.3827 0.155 Uiso 1 1 calc R . . H20F H 1.0416 0.0177 0.3624 0.155 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 S1 0.0627(14) 0.0592(15) 0.0687(13) -0.0155(11) 0.0428(11) -0.0332(11) S2 0.0350(10) 0.0590(13) 0.0302(9) -0.0104(8) 0.0087(7) -0.0217(9) F22 0.036(2) 0.060(3) 0.044(2) 0.011(2) -0.0026(18) -0.016(2) F23 0.027(2) 0.063(3) 0.075(3) 0.002(2) 0.004(2) -0.014(2) F25 0.077(3) 0.060(3) 0.033(2) 0.010(2) 0.010(2) -0.028(2) F26 0.038(2) 0.055(3) 0.037(2) 0.0082(19) -0.0078(17) -0.0115(19) F32 0.046(2) 0.045(3) 0.038(2) 0.0058(18) -0.0113(18) -0.0123(19) F33 0.051(3) 0.044(3) 0.047(2) -0.006(2) -0.0026(19) -0.012(2) F35 0.046(2) 0.057(3) 0.034(2) -0.0005(19) -0.0146(18) -0.006(2) F36 0.055(3) 0.052(3) 0.037(2) -0.0081(19) -0.0090(19) 0.003(2) F63B 0.045(2) 0.050(3) 0.061(3) -0.010(2) 0.022(2) -0.022(2) F63A 0.028(2) 0.092(4) 0.032(2) 0.002(2) 0.0020(17) -0.010(2) F64B 0.036(2) 0.079(3) 0.0253(19) 0.011(2) 0.0000(16) -0.002(2) F64A 0.040(2) 0.053(3) 0.054(2) -0.013(2) 0.0179(19) -0.024(2) F65A 0.035(2) 0.044(3) 0.047(2) -0.0071(18) 0.0092(17) -0.0170(19) F65B 0.032(2) 0.060(3) 0.033(2) 0.0110(19) 0.0058(16) -0.0068(19) F66A 0.032(2) 0.068(3) 0.039(2) -0.017(2) 0.0070(17) -0.020(2) F66B 0.035(2) 0.070(3) 0.040(2) 0.023(2) 0.0051(18) -0.001(2) F67A 0.031(2) 0.043(3) 0.039(2) 0.0075(18) 0.0057(16) -0.0070(17) F67B 0.032(2) 0.058(3) 0.039(2) -0.0127(19) 0.0092(17) -0.019(2) F68A 0.034(2) 0.047(3) 0.050(2) 0.012(2) 0.0068(18) -0.0099(19) F68B 0.029(2) 0.072(3) 0.034(2) -0.007(2) 0.0024(16) -0.014(2) F69A 0.035(2) 0.067(3) 0.0273(19) 0.0005(18) 0.0008(16) -0.012(2) F69B 0.037(2) 0.040(3) 0.054(2) -0.0002(19) 0.0162(18) -0.0125(19) F70A 0.031(2) 0.054(3) 0.0309(19) 0.0003(17) -0.0005(16) -0.0134(18) F70B 0.034(2) 0.044(3) 0.043(2) -0.0013(18) 0.0075(17) -0.0150(19) F71A 0.037(2) 0.042(3) 0.052(2) -0.0001(19) 0.0089(18) -0.0177(19) F71B 0.036(2) 0.059(3) 0.036(2) 0.0108(19) 0.0026(17) -0.011(2) F72A 0.041(2) 0.063(3) 0.062(3) 0.010(2) 0.024(2) -0.009(2) F72B 0.031(2) 0.059(3) 0.052(2) 0.004(2) -0.0031(19) -0.009(2) F72C 0.041(2) 0.059(3) 0.050(2) -0.015(2) 0.0088(19) -0.013(2) F83A 0.031(2) 0.056(3) 0.0278(19) -0.0018(17) 0.0029(16) -0.0141(18) F83B 0.042(2) 0.045(3) 0.044(2) -0.0116(19) 0.0099(18) -0.014(2) F84A 0.037(2) 0.060(3) 0.030(2) 0.0070(18) 0.0052(17) -0.0085(19) F84B 0.044(2) 0.040(3) 0.057(2) -0.006(2) 0.0156(19) -0.020(2) F85A 0.043(2) 0.043(3) 0.050(2) -0.0032(19) 0.0157(19) -0.0162(19) F85B 0.031(2) 0.074(3) 0.030(2) 0.0021(19) 0.0003(16) -0.013(2) F86A 0.036(2) 0.041(3) 0.053(2) 0.0091(19) 0.0144(18) -0.0091(18) F86B 0.034(2) 0.071(3) 0.0289(19) -0.0095(19) 0.0038(16) -0.018(2) F87A 0.038(2) 0.046(3) 0.044(2) 0.0098(19) 0.0088(17) -0.0086(19) F87B 0.034(2) 0.069(3) 0.032(2) -0.0146(19) 0.0015(16) -0.019(2) F88A 0.039(2) 0.059(3) 0.039(2) -0.0131(19) 0.0041(17) -0.028(2) F88B 0.039(2) 0.054(3) 0.033(2) 0.0101(18) 0.0036(17) -0.0139(19) F89A 0.035(2) 0.048(3) 0.0311(19) 0.0105(18) 0.0027(16) -0.0077(18) F89B 0.031(2) 0.042(3) 0.039(2) -0.0015(17) 0.0023(16) -0.0170(18) F90A 0.033(2) 0.073(3) 0.031(2) 0.008(2) -0.0015(16) -0.015(2) F90B 0.043(2) 0.053(3) 0.044(2) -0.0047(19) 0.0082(18) -0.026(2) F91A 0.036(2) 0.063(3) 0.0292(19) 0.0004(18) 0.0009(16) -0.019(2) F91B 0.043(2) 0.049(3) 0.051(2) 0.001(2) 0.0049(19) -0.013(2) F92A 0.048(3) 0.078(4) 0.054(3) 0.006(2) 0.010(2) -0.033(2) F92B 0.038(3) 0.111(4) 0.061(3) -0.028(3) 0.018(2) -0.024(3) F92C 0.032(2) 0.101(4) 0.054(3) 0.009(3) -0.005(2) -0.019(2) N1 0.022(3) 0.039(3) 0.023(3) 0.002(2) 0.002(2) -0.009(2) N2 0.025(3) 0.040(4) 0.022(3) -0.004(2) 0.009(2) -0.009(2) C1 0.029(4) 0.038(4) 0.031(3) 0.003(3) 0.004(3) -0.011(3) C2 0.032(4) 0.045(5) 0.028(3) -0.006(3) 0.003(3) -0.011(3) C3 0.035(4) 0.040(5) 0.035(4) -0.001(3) 0.006(3) -0.019(3) C4 0.021(3) 0.036(4) 0.028(3) 0.001(3) 0.006(3) -0.004(3) C5 0.026(3) 0.038(4) 0.021(3) 0.002(3) 0.002(2) -0.011(3) C6 0.020(3) 0.039(4) 0.030(3) 0.000(3) 0.005(3) 0.000(3) C7 0.027(3) 0.047(5) 0.029(3) 0.008(3) 0.005(3) -0.013(3) C8 0.033(4) 0.042(5) 0.025(3) -0.003(3) 0.009(3) -0.009(3) C9 0.028(3) 0.033(4) 0.025(3) -0.002(3) 0.004(3) -0.006(3) C10 0.029(4) 0.034(4) 0.030(3) -0.004(3) 0.004(3) -0.009(3) C21 0.026(3) 0.043(4) 0.025(3) -0.003(3) 0.006(3) -0.013(3) C22 0.030(4) 0.052(5) 0.031(3) 0.007(3) 0.000(3) -0.013(3) C23 0.018(3) 0.045(5) 0.058(5) -0.003(4) 0.009(3) -0.009(3) C24 0.037(4) 0.036(4) 0.042(4) -0.006(3) 0.023(3) -0.012(3) C25 0.054(5) 0.050(5) 0.024(3) 0.006(3) 0.007(3) -0.021(4) C26 0.024(3) 0.047(5) 0.027(3) 0.004(3) 0.009(3) -0.002(3) C31 0.026(3) 0.039(5) 0.026(3) -0.001(3) 0.007(3) -0.012(3) C32 0.026(3) 0.034(4) 0.030(3) -0.002(3) -0.001(3) -0.010(3) C33 0.027(3) 0.030(4) 0.039(4) 0.001(3) 0.004(3) -0.006(3) C34 0.029(4) 0.045(5) 0.030(3) -0.009(3) 0.007(3) -0.015(3) C35 0.025(3) 0.048(5) 0.029(3) 0.001(3) 0.000(3) -0.004(3) C36 0.033(4) 0.034(5) 0.032(4) -0.008(3) 0.007(3) 0.000(3) C61 0.037(4) 0.067(6) 0.042(4) -0.004(4) 0.015(3) -0.017(4) C62 0.034(4) 0.046(5) 0.038(4) 0.001(3) 0.007(3) -0.012(3) C63 0.044(4) 0.045(5) 0.028(3) 0.004(3) 0.003(3) -0.021(4) C64 0.030(4) 0.038(5) 0.036(4) 0.004(3) 0.006(3) -0.012(3) C65 0.031(4) 0.029(4) 0.032(3) 0.007(3) 0.004(3) -0.007(3) C66 0.035(4) 0.043(5) 0.025(3) 0.001(3) 0.003(3) -0.009(3) C67 0.035(4) 0.040(5) 0.032(3) -0.001(3) 0.009(3) -0.019(3) C68 0.035(4) 0.041(5) 0.031(3) -0.002(3) -0.002(3) -0.018(3) C69 0.027(4) 0.038(5) 0.035(4) 0.000(3) 0.003(3) -0.011(3) C70 0.031(4) 0.041(5) 0.032(3) 0.000(3) -0.001(3) -0.019(3) C71 0.025(3) 0.033(4) 0.038(4) 0.001(3) -0.001(3) -0.008(3) C72 0.020(3) 0.038(5) 0.045(4) 0.005(3) 0.005(3) -0.004(3) C81 0.041(4) 0.042(5) 0.035(4) -0.004(3) 0.013(3) -0.012(3) C82 0.038(4) 0.042(4) 0.029(3) -0.002(3) 0.014(3) -0.014(3) C83 0.027(3) 0.042(4) 0.024(3) -0.005(3) -0.005(3) -0.012(3) C84 0.035(4) 0.041(5) 0.024(3) 0.007(3) -0.003(3) -0.012(3) C85 0.033(4) 0.040(5) 0.030(3) -0.008(3) 0.001(3) -0.019(3) C86 0.030(4) 0.045(5) 0.033(4) -0.005(3) 0.002(3) -0.020(3) C87 0.037(4) 0.041(5) 0.029(3) -0.002(3) 0.005(3) -0.015(3) C88 0.028(3) 0.031(4) 0.027(3) -0.002(3) 0.003(3) -0.008(3) C89 0.031(4) 0.032(4) 0.035(4) -0.002(3) 0.002(3) -0.012(3) C90 0.038(4) 0.037(4) 0.029(3) 0.001(3) 0.001(3) -0.015(3) C91 0.036(4) 0.046(5) 0.034(4) 0.006(3) -0.003(3) -0.014(3) C92 0.027(4) 0.068(6) 0.043(4) -0.001(4) 0.003(3) -0.017(4) O101 0.087(5) 0.123(6) 0.058(4) -0.008(4) -0.033(4) 0.047(4) C101 0.068(6) 0.057(6) 0.059(5) -0.001(4) -0.014(5) 0.013(5) C102 0.065(6) 0.096(8) 0.066(6) 0.007(5) -0.022(5) -0.014(5) C103 0.098(8) 0.072(7) 0.077(6) 0.016(5) -0.017(6) -0.034(6) O201 0.053(4) 0.091(5) 0.088(4) -0.021(4) 0.032(3) -0.033(4) C201 0.043(5) 0.053(5) 0.045(4) -0.004(4) 0.014(4) 0.002(4) C202 0.054(5) 0.108(8) 0.052(5) -0.012(5) 0.006(4) -0.047(5) C203 0.145(11) 0.084(8) 0.060(6) -0.002(6) -0.009(6) 0.022(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C24 1.763(6) . ? S1 C61 1.819(7) . ? S2 C34 1.778(6) . ? S2 C81 1.825(6) . ? F22 C22 1.355(7) . ? F23 C23 1.354(7) . ? F25 C25 1.339(7) . ? F26 C26 1.332(7) . ? F32 C32 1.349(7) . ? F33 C33 1.332(7) . ? F35 C35 1.361(7) . ? F36 C36 1.350(8) . ? F63B C63 1.351(7) . ? F63A C63 1.362(7) . ? F64B C64 1.352(7) . ? F64A C64 1.349(7) . ? F65A C65 1.337(7) . ? F65B C65 1.352(7) . ? F66A C66 1.346(7) . ? F66B C66 1.347(7) . ? F67A C67 1.338(7) . ? F67B C67 1.336(7) . ? F68A C68 1.341(7) . ? F68B C68 1.342(7) . ? F69A C69 1.349(7) . ? F69B C69 1.341(7) . ? F70A C70 1.348(7) . ? F70B C70 1.332(7) . ? F71A C71 1.353(7) . ? F71B C71 1.342(7) . ? F72A C72 1.337(6) . ? F72B C72 1.320(7) . ? F72C C72 1.327(7) . ? F83A C83 1.357(6) . ? F83B C83 1.363(7) . ? F84A C84 1.351(7) . ? F84B C84 1.349(7) . ? F85A C85 1.334(7) . ? F85B C85 1.342(7) . ? F86A C86 1.334(7) . ? F86B C86 1.348(7) . ? F87A C87 1.333(7) . ? F87B C87 1.343(7) . ? F88A C88 1.340(7) . ? F88B C88 1.342(7) . ? F89A C89 1.352(7) . ? F89B C89 1.339(7) . ? F90A C90 1.358(7) . ? F90B C90 1.333(7) . ? F91A C91 1.369(7) . ? F91B C91 1.336(8) . ? F92A C92 1.314(8) . ? F92B C92 1.319(8) . ? F92C C92 1.340(8) . ? N1 C1 1.367(8) . ? N1 C4 1.385(6) . ? N2 C9 1.360(7) . ? N2 C6 1.377(7) . ? C1 C10 1.399(8) 2_666 ? C1 C2 1.434(8) . ? C2 C3 1.350(8) . ? C3 C4 1.428(8) . ? C4 C5 1.399(8) . ? C5 C6 1.388(8) . ? C5 C21 1.491(7) . ? C6 C7 1.441(8) . ? C7 C8 1.332(8) . ? C8 C9 1.453(7) . ? C9 C10 1.386(8) . ? C10 C1 1.399(8) 2_666 ? C10 C31 1.502(8) . ? C21 C22 1.371(8) . ? C21 C26 1.394(8) . ? C22 C23 1.386(8) . ? C23 C24 1.362(9) . ? C24 C25 1.390(9) . ? C25 C26 1.389(8) . ? C31 C32 1.363(9) . ? C31 C36 1.407(9) . ? C32 C33 1.371(8) . ? C33 C34 1.395(9) . ? C34 C35 1.349(9) . ? C35 C36 1.364(9) . ? C61 C62 1.509(8) . ? C62 C63 1.488(9) . ? C63 C64 1.531(8) . ? C64 C65 1.535(8) . ? C65 C66 1.544(8) . ? C66 C67 1.556(8) . ? C67 C68 1.557(9) . ? C68 C69 1.552(8) . ? C69 C70 1.561(9) . ? C70 C71 1.553(8) . ? C71 C72 1.526(9) . ? C81 C82 1.519(9) . ? C82 C83 1.514(7) . ? C83 C84 1.526(9) . ? C84 C85 1.555(8) . ? C85 C86 1.563(9) . ? C86 C87 1.552(8) . ? C87 C88 1.562(9) . ? C88 C89 1.561(8) . ? C89 C90 1.539(8) . ? C90 C91 1.538(9) . ? C91 C92 1.525(9) . ? O101 C101 1.215(10) . ? C101 C103 1.479(12) . ? C101 C102 1.482(11) . ? O201 C201 1.196(9) . ? C201 C203 1.484(11) . ? C201 C202 1.485(10) . ? 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 C24 S1 C61 102.6(3) . . ? C34 S2 C81 100.1(3) . . ? C1 N1 C4 108.3(5) . . ? C9 N2 C6 107.4(5) . . ? N1 C1 C10 124.9(5) . 2_666 ? N1 C1 C2 108.2(5) . . ? C10 C1 C2 126.9(6) 2_666 . ? C3 C2 C1 107.7(6) . . ? C2 C3 C4 108.2(5) . . ? N1 C4 C5 124.0(5) . . ? N1 C4 C3 107.6(5) . . ? C5 C4 C3 128.4(5) . . ? C6 C5 C4 126.0(5) . . ? C6 C5 C21 118.0(5) . . ? C4 C5 C21 116.0(5) . . ? N2 C6 C5 126.3(5) . . ? N2 C6 C7 108.8(5) . . ? C5 C6 C7 124.9(5) . . ? C8 C7 C6 107.5(5) . . ? C7 C8 C9 107.7(6) . . ? N2 C9 C10 126.5(5) . . ? N2 C9 C8 108.6(5) . . ? C10 C9 C8 124.8(6) . . ? C9 C10 C1 127.8(6) . 2_666 ? C9 C10 C31 115.6(5) . . ? C1 C10 C31 116.7(5) 2_666 . ? C22 C21 C26 115.9(5) . . ? C22 C21 C5 121.7(5) . . ? C26 C21 C5 122.4(6) . . ? F22 C22 C21 119.7(5) . . ? F22 C22 C23 117.9(6) . . ? C21 C22 C23 122.4(6) . . ? F23 C23 C24 120.9(5) . . ? F23 C23 C22 117.2(6) . . ? C24 C23 C22 121.9(6) . . ? C23 C24 C25 116.9(5) . . ? C23 C24 S1 121.0(5) . . ? C25 C24 S1 121.7(5) . . ? F25 C25 C26 118.2(6) . . ? F25 C25 C24 120.6(5) . . ? C26 C25 C24 121.1(6) . . ? F26 C26 C25 118.5(6) . . ? F26 C26 C21 119.8(5) . . ? C25 C26 C21 121.7(6) . . ? C32 C31 C36 116.1(6) . . ? C32 C31 C10 123.8(6) . . ? C36 C31 C10 119.9(6) . . ? F32 C32 C31 119.4(5) . . ? F32 C32 C33 118.2(6) . . ? C31 C32 C33 122.3(6) . . ? F33 C33 C32 119.2(6) . . ? F33 C33 C34 119.7(6) . . ? C32 C33 C34 121.0(6) . . ? C35 C34 C33 116.9(6) . . ? C35 C34 S2 121.2(5) . . ? C33 C34 S2 121.9(6) . . ? C34 C35 F35 120.7(6) . . ? C34 C35 C36 122.6(6) . . ? F35 C35 C36 116.7(6) . . ? F36 C36 C35 120.4(6) . . ? F36 C36 C31 118.5(6) . . ? C35 C36 C31 121.1(6) . . ? C62 C61 S1 108.0(5) . . ? C63 C62 C61 114.2(6) . . ? F63B C63 F63A 105.5(5) . . ? F63B C63 C62 110.6(5) . . ? F63A C63 C62 111.1(6) . . ? F63B C63 C64 108.7(6) . . ? F63A C63 C64 106.7(5) . . ? C62 C63 C64 113.8(6) . . ? F64A C64 F64B 107.1(5) . . ? F64A C64 C63 107.7(5) . . ? F64B C64 C63 107.6(5) . . ? F64A C64 C65 107.9(4) . . ? F64B C64 C65 107.8(5) . . ? C63 C64 C65 118.2(5) . . ? F65A C65 F65B 108.0(5) . . ? F65A C65 C64 109.0(4) . . ? F65B C65 C64 108.0(5) . . ? F65A C65 C66 108.8(5) . . ? F65B C65 C66 108.0(4) . . ? C64 C65 C66 114.7(5) . . ? F66A C66 F66B 108.3(5) . . ? F66A C66 C65 109.0(5) . . ? F66B C66 C65 108.3(5) . . ? F66A C66 C67 108.6(5) . . ? F66B C66 C67 107.7(5) . . ? C65 C66 C67 114.9(5) . . ? F67B C67 F67A 109.3(5) . . ? F67B C67 C66 108.4(5) . . ? F67A C67 C66 108.3(5) . . ? F67B C67 C68 108.6(5) . . ? F67A C67 C68 108.7(5) . . ? C66 C67 C68 113.5(5) . . ? F68A C68 F68B 108.2(5) . . ? F68A C68 C69 108.6(5) . . ? F68B C68 C69 108.3(5) . . ? F68A C68 C67 109.2(5) . . ? F68B C68 C67 108.9(5) . . ? C69 C68 C67 113.5(5) . . ? F69B C69 F69A 108.6(5) . . ? F69B C69 C68 108.5(5) . . ? F69A C69 C68 108.2(5) . . ? F69B C69 C70 108.8(5) . . ? F69A C69 C70 108.8(5) . . ? C68 C69 C70 113.9(5) . . ? F70B C70 F70A 108.9(5) . . ? F70B C70 C71 109.4(5) . . ? F70A C70 C71 108.3(5) . . ? F70B C70 C69 108.6(5) . . ? F70A C70 C69 108.6(5) . . ? C71 C70 C69 113.0(5) . . ? F71B C71 F71A 108.9(5) . . ? F71B C71 C72 108.6(5) . . ? F71A C71 C72 106.9(5) . . ? F71B C71 C70 108.6(5) . . ? F71A C71 C70 108.0(5) . . ? C72 C71 C70 115.7(5) . . ? F72B C72 F72C 108.9(5) . . ? F72B C72 F72A 108.6(5) . . ? F72C C72 F72A 107.6(5) . . ? F72B C72 C71 111.7(5) . . ? F72C C72 C71 111.8(5) . . ? F72A C72 C71 108.2(5) . . ? C82 C81 S2 111.9(4) . . ? C83 C82 C81 111.3(5) . . ? F83A C83 F83B 106.2(5) . . ? F83A C83 C82 110.4(5) . . ? F83B C83 C82 110.1(5) . . ? F83A C83 C84 107.2(5) . . ? F83B C83 C84 108.5(5) . . ? C82 C83 C84 114.1(5) . . ? F84B C84 F84A 108.5(5) . . ? F84B C84 C83 107.8(5) . . ? F84A C84 C83 109.3(5) . . ? F84B C84 C85 107.1(5) . . ? F84A C84 C85 107.7(5) . . ? C83 C84 C85 116.2(5) . . ? F85A C85 F85B 108.6(5) . . ? F85A C85 C84 108.9(5) . . ? F85B C85 C84 108.6(5) . . ? F85A C85 C86 108.3(5) . . ? F85B C85 C86 107.8(5) . . ? C84 C85 C86 114.5(5) . . ? F86A C86 F86B 108.4(5) . . ? F86A C86 C87 109.3(5) . . ? F86B C86 C87 108.1(5) . . ? F86A C86 C85 109.6(5) . . ? F86B C86 C85 108.4(5) . . ? C87 C86 C85 112.9(5) . . ? F87A C87 F87B 109.3(5) . . ? F87A C87 C86 109.3(5) . . ? F87B C87 C86 108.5(5) . . ? F87A C87 C88 108.3(5) . . ? F87B C87 C88 107.7(5) . . ? C86 C87 C88 113.6(5) . . ? F88A C88 F88B 108.8(5) . . ? F88A C88 C89 108.7(4) . . ? F88B C88 C89 108.5(5) . . ? F88A C88 C87 107.9(5) . . ? F88B C88 C87 109.1(5) . . ? C89 C88 C87 113.8(5) . . ? F89B C89 F89A 109.1(5) . . ? F89B C89 C90 109.7(5) . . ? F89A C89 C90 108.0(5) . . ? F89B C89 C88 108.5(5) . . ? F89A C89 C88 107.7(5) . . ? C90 C89 C88 113.7(5) . . ? F90B C90 F90A 108.1(5) . . ? F90B C90 C91 109.1(5) . . ? F90A C90 C91 106.6(5) . . ? F90B C90 C89 109.6(5) . . ? F90A C90 C89 108.6(5) . . ? C91 C90 C89 114.7(5) . . ? F91B C91 F91A 107.7(5) . . ? F91B C91 C92 108.2(6) . . ? F91A C91 C92 106.1(5) . . ? F91B C91 C90 110.4(5) . . ? F91A C91 C90 107.3(5) . . ? C92 C91 C90 116.8(6) . . ? F92A C92 F92B 109.0(6) . . ? F92A C92 F92C 108.1(6) . . ? F92B C92 F92C 108.0(6) . . ? F92A C92 C91 113.0(6) . . ? F92B C92 C91 109.5(6) . . ? F92C C92 C91 109.1(5) . . ? O101 C101 C103 122.7(9) . . ? O101 C101 C102 120.7(9) . . ? C103 C101 C102 116.6(8) . . ? O201 C201 C203 123.1(8) . . ? O201 C201 C202 121.0(8) . . ? C203 C201 C202 115.8(8) . . ? _diffrn_measured_fraction_theta_max 0.861 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.861 _refine_diff_density_max 0.380 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.086