# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Peter Wipf' _publ_contact_author_name 'Peter Wipf' _publ_contact_author_email PWIPF@PITT.EDU _publ_section_title ; Synthesis and biological evaluation of the first pentafluorosulfanyl analogs of mefloquine ; # Attachment 'Cmpd_3.cif' data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 735960' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 F8 N2 O S, C H4 O' _chemical_formula_sum 'C17 H20 F8 N2 O2 S' _chemical_formula_weight 468.41 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.098(3) _cell_length_b 23.909(3) _cell_length_c 17.404(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.994(3) _cell_angle_gamma 90.00 _cell_volume 8250.2(18) _cell_formula_units_Z 16 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 5879 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 21.57 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3840 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9438 _exptl_absorpt_correction_T_max 0.9667 _exptl_absorpt_process_details 'Bruker Sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39637 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 9475 _reflns_number_gt 6120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[s^2^(Fo^2^)+(0.0780P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9475 _refine_ls_number_parameters 567 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 S1 S 0.35945(3) 0.12643(3) 0.65187(4) 0.05068(19) Uani 1 1 d . . . O1 O 0.55084(9) -0.17628(7) 0.65299(12) 0.0426(4) Uani 1 1 d . . . H1O H 0.5759(15) -0.1726(12) 0.6972(19) 0.063(10) Uiso 1 1 d . . . N1 N 0.56436(9) 0.03237(7) 0.61676(12) 0.0391(4) Uani 1 1 d . . . F1 F 0.29281(8) 0.10032(7) 0.59183(12) 0.0782(5) Uani 1 1 d . . . C1 C 0.50471(11) 0.02304(9) 0.62964(13) 0.0343(5) Uani 1 1 d . . . N2 N 0.40879(10) -0.20605(8) 0.57854(12) 0.0383(4) Uani 1 1 d . . . H2N H 0.4367(12) -0.2323(10) 0.5927(14) 0.035(6) Uiso 1 1 d . . . C2 C 0.46756(11) 0.07086(9) 0.63578(14) 0.0373(5) Uani 1 1 d . . . H2A H 0.4842 0.1068 0.6317 0.045 Uiso 1 1 calc R . . F2 F 0.34209(10) 0.10334(7) 0.72682(12) 0.0784(5) Uani 1 1 d . . . S2 S 0.13782(4) 0.12947(3) 0.27608(4) 0.05277(19) Uani 1 1 d . . . O2 O -0.03462(9) -0.17867(6) 0.11356(11) 0.0430(4) Uani 1 1 d . . . H2O H -0.0643(15) -0.1713(11) 0.1300(17) 0.053(9) Uiso 1 1 d . . . F3 F 0.31767(8) 0.18056(7) 0.65547(13) 0.0769(5) Uani 1 1 d . . . C3 C 0.40745(11) 0.06464(9) 0.64770(14) 0.0381(5) Uani 1 1 d . . . N3 N -0.05734(9) 0.02882(7) 0.06134(12) 0.0385(4) Uani 1 1 d . . . O3 O 0.63688(9) -0.16719(9) 0.80615(12) 0.0548(5) Uani 1 1 d . . . H3O H 0.6257(16) -0.1839(13) 0.839(2) 0.074(11) Uiso 1 1 d . . . F4 F 0.42346(9) 0.15667(7) 0.71254(12) 0.0745(5) Uani 1 1 d . . . C4 C 0.38215(11) 0.01150(10) 0.65593(15) 0.0411(5) Uani 1 1 d . . . H4A H 0.3407 0.0081 0.6645 0.049 Uiso 1 1 calc R . . N4 N 0.10856(10) -0.20437(8) 0.17555(13) 0.0394(5) Uani 1 1 d . . . H4N H 0.0815(12) -0.2299(10) 0.1622(14) 0.034(6) Uiso 1 1 d . . . O4 O 0.13456(9) -0.16511(9) 0.32632(13) 0.0553(5) Uani 1 1 d . . . H4O H 0.1279(13) -0.1827(12) 0.2801(18) 0.057(9) Uiso 1 1 d . . . F5 F 0.37410(9) 0.15388(7) 0.57760(12) 0.0755(5) Uani 1 1 d . . . C5 C 0.41813(11) -0.03524(10) 0.65140(14) 0.0399(5) Uani 1 1 d . . . H5A H 0.4015 -0.0707 0.6581 0.048 Uiso 1 1 calc R . . C6 C 0.48015(11) -0.03110(9) 0.63682(13) 0.0338(5) Uani 1 1 d . . . F6 F 0.66327(9) 0.04438(8) 0.55421(13) 0.0859(6) Uani 1 1 d . . . C7 C 0.52000(11) -0.07788(9) 0.62993(13) 0.0347(5) Uani 1 1 d . . . F7 F 0.71274(8) 0.01018(9) 0.67134(12) 0.0868(6) Uani 1 1 d . . . C8 C 0.57956(11) -0.06757(9) 0.61731(14) 0.0390(5) Uani 1 1 d . . . H8A H 0.6072 -0.0974 0.6129 0.047 Uiso 1 1 calc R . . F8 F 0.68744(9) -0.04195(7) 0.56751(13) 0.0815(6) Uani 1 1 d . . . C9 C 0.59884(11) -0.01209(9) 0.61100(14) 0.0376(5) Uani 1 1 d . . . F9 F 0.20738(7) 0.10274(7) 0.28056(10) 0.0652(4) Uani 1 1 d . . . C10 C 0.49753(11) -0.13716(9) 0.63720(14) 0.0366(5) Uani 1 1 d . . . H10A H 0.4798 -0.1386 0.6830 0.044 Uiso 1 1 calc R . . F10 F 0.14957(10) 0.10747(7) 0.36508(10) 0.0769(5) Uani 1 1 d . . . C11 C 0.44135(12) -0.15607(9) 0.55880(14) 0.0378(5) Uani 1 1 d . . . H11A H 0.4071 -0.1259 0.5428 0.045 Uiso 1 1 calc R . . F11 F 0.17787(9) 0.18387(7) 0.31593(12) 0.0801(6) Uani 1 1 d . . . C12 C 0.35408(13) -0.22727(11) 0.50643(16) 0.0523(7) Uani 1 1 d . . . H12A H 0.3170 -0.2001 0.4911 0.063 Uiso 1 1 calc R . . H12B H 0.3369 -0.2622 0.5211 0.063 Uiso 1 1 calc R . . F12 F 0.07193(9) 0.15978(7) 0.27540(14) 0.0909(7) Uani 1 1 d . . . C13 C 0.37587(15) -0.23782(11) 0.43331(17) 0.0573(7) Uani 1 1 d . . . H13A H 0.4080 -0.2690 0.4453 0.069 Uiso 1 1 calc R . . H13B H 0.3365 -0.2483 0.3861 0.069 Uiso 1 1 calc R . . F13 F 0.13075(10) 0.15478(7) 0.19006(11) 0.0795(6) Uani 1 1 d . . . C14 C 0.40844(16) -0.18616(12) 0.41274(16) 0.0622(8) Uani 1 1 d . . . H14A H 0.3746 -0.1565 0.3934 0.075 Uiso 1 1 calc R . . H14B H 0.4260 -0.1949 0.3688 0.075 Uiso 1 1 calc R . . F14 F -0.15940(9) 0.03797(8) -0.08143(11) 0.0823(6) Uani 1 1 d . . . C15 C 0.46581(15) -0.16577(11) 0.48774(15) 0.0535(7) Uani 1 1 d . . . H15A H 0.5021 -0.1936 0.5031 0.064 Uiso 1 1 calc R . . H15B H 0.4841 -0.1308 0.4746 0.064 Uiso 1 1 calc R . . F15 F -0.20477(8) -0.00604(11) -0.00889(12) 0.0957(7) Uani 1 1 d . . . C16 C 0.66515(12) 0.00018(11) 0.60033(18) 0.0492(6) Uani 1 1 d . . . F16 F -0.17111(9) -0.04885(8) -0.09326(12) 0.0887(6) Uani 1 1 d . . . C17 C 0.00136(11) 0.02211(9) 0.12626(13) 0.0359(5) Uani 1 1 d . . . C18 C 0.03547(12) 0.07105(9) 0.16363(15) 0.0408(5) Uani 1 1 d . . . H18A H 0.0188 0.1064 0.1427 0.049 Uiso 1 1 calc R . . C19 C 0.09265(11) 0.06668(9) 0.23027(14) 0.0385(5) Uani 1 1 d . . . C20 C 0.11768(11) 0.01462(9) 0.26380(14) 0.0389(5) Uani 1 1 d . . . H20A H 0.1566 0.0126 0.3107 0.047 Uiso 1 1 calc R . . C21 C 0.08554(11) -0.03316(9) 0.22841(14) 0.0385(5) Uani 1 1 d . . . H21A H 0.1026 -0.0680 0.2514 0.046 Uiso 1 1 calc R . . C22 C 0.02695(11) -0.03128(9) 0.15758(14) 0.0341(5) Uani 1 1 d . . . C23 C -0.00855(11) -0.07936(9) 0.11660(13) 0.0344(5) Uani 1 1 d . . . C24 C -0.06662(11) -0.07159(9) 0.05188(14) 0.0389(5) Uani 1 1 d . . . H24A H -0.0916 -0.1024 0.0238 0.047 Uiso 1 1 calc R . . C25 C -0.08855(11) -0.01678(9) 0.02789(14) 0.0372(5) Uani 1 1 d . . . C26 C 0.01605(11) -0.13777(9) 0.14622(14) 0.0352(5) Uani 1 1 d . . . H26A H 0.0288 -0.1383 0.2065 0.042 Uiso 1 1 calc R . . C27 C 0.07809(11) -0.15531(9) 0.12471(14) 0.0372(5) Uani 1 1 d . . . H27A H 0.1112 -0.1244 0.1411 0.045 Uiso 1 1 calc R . . C28 C 0.16914(12) -0.22442(11) 0.15917(18) 0.0528(7) Uani 1 1 d . . . H28A H 0.1858 -0.2584 0.1912 0.063 Uiso 1 1 calc R . . H28B H 0.2046 -0.1960 0.1776 0.063 Uiso 1 1 calc R . . C29 C 0.15614(14) -0.23687(11) 0.07048(18) 0.0579(7) Uani 1 1 d . . . H29A H 0.1251 -0.2686 0.0534 0.069 Uiso 1 1 calc R . . H29B H 0.1986 -0.2472 0.0629 0.069 Uiso 1 1 calc R . . C30 C 0.12599(15) -0.18664(12) 0.01792(18) 0.0596(7) Uani 1 1 d . . . H30A H 0.1140 -0.1967 -0.0399 0.071 Uiso 1 1 calc R . . H30B H 0.1595 -0.1565 0.0297 0.071 Uiso 1 1 calc R . . C31 C 0.06288(13) -0.16583(11) 0.03400(15) 0.0480(6) Uani 1 1 d . . . H31A H 0.0470 -0.1311 0.0035 0.058 Uiso 1 1 calc R . . H31B H 0.0270 -0.1938 0.0146 0.058 Uiso 1 1 calc R . . C32 C -0.15605(12) -0.00781(11) -0.03882(16) 0.0467(6) Uani 1 1 d . . . C33 C 0.70559(15) -0.15559(18) 0.8373(2) 0.0904(12) Uani 1 1 d . . . H33A H 0.7176 -0.1313 0.7998 0.136 Uiso 1 1 calc R . . H33B H 0.7309 -0.1902 0.8440 0.136 Uiso 1 1 calc R . . H33C H 0.7163 -0.1372 0.8899 0.136 Uiso 1 1 calc R . . C34 C 0.20084(15) -0.14757(17) 0.3621(2) 0.0851(11) Uani 1 1 d . . . H34A H 0.2125 -0.1227 0.3250 0.128 Uiso 1 1 calc R . . H34B H 0.2305 -0.1798 0.3738 0.128 Uiso 1 1 calc R . . H34C H 0.2058 -0.1279 0.4126 0.128 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 0.0448(4) 0.0417(3) 0.0711(5) -0.0017(3) 0.0270(3) 0.0098(3) O1 0.0448(10) 0.0317(8) 0.0469(11) 0.0025(7) 0.0101(8) 0.0079(7) N1 0.0353(10) 0.0346(10) 0.0506(12) 0.0008(9) 0.0190(9) 0.0002(8) F1 0.0397(9) 0.0689(11) 0.1130(15) -0.0105(10) 0.0095(9) 0.0135(8) C1 0.0333(11) 0.0339(11) 0.0365(12) -0.0012(9) 0.0128(9) -0.0004(9) N2 0.0344(10) 0.0306(10) 0.0449(11) 0.0028(8) 0.0072(8) 0.0027(8) C2 0.0370(12) 0.0315(11) 0.0451(13) 0.0006(10) 0.0163(10) 0.0023(9) F2 0.0959(14) 0.0696(11) 0.0964(14) 0.0033(10) 0.0673(12) 0.0222(10) S2 0.0529(4) 0.0396(3) 0.0652(5) -0.0085(3) 0.0194(3) -0.0141(3) O2 0.0377(9) 0.0301(8) 0.0645(12) -0.0041(7) 0.0219(9) -0.0058(7) F3 0.0636(11) 0.0520(10) 0.1270(16) -0.0043(10) 0.0479(11) 0.0208(8) C3 0.0369(12) 0.0353(11) 0.0428(13) -0.0025(10) 0.0146(10) 0.0075(9) N3 0.0380(10) 0.0328(10) 0.0449(11) 0.0036(8) 0.0145(8) 0.0047(8) O3 0.0378(10) 0.0746(13) 0.0520(12) 0.0073(10) 0.0155(8) -0.0023(9) F4 0.0602(10) 0.0535(9) 0.1062(14) -0.0310(9) 0.0240(9) 0.0042(8) C4 0.0332(12) 0.0418(12) 0.0515(14) -0.0002(11) 0.0189(10) 0.0013(10) N4 0.0317(10) 0.0323(10) 0.0559(13) 0.0044(9) 0.0171(9) 0.0000(8) O4 0.0380(10) 0.0706(13) 0.0559(12) -0.0064(10) 0.0142(8) -0.0037(9) F5 0.0887(13) 0.0571(10) 0.0957(13) 0.0291(9) 0.0510(11) 0.0320(9) C5 0.0379(12) 0.0365(12) 0.0473(14) 0.0000(10) 0.0170(10) -0.0033(10) C6 0.0344(11) 0.0316(11) 0.0349(12) -0.0001(9) 0.0111(9) 0.0000(9) F6 0.0600(11) 0.0794(12) 0.1376(17) 0.0496(12) 0.0584(11) 0.0154(9) C7 0.0353(12) 0.0317(11) 0.0358(12) -0.0001(9) 0.0105(9) 0.0013(9) F7 0.0379(9) 0.1261(17) 0.0926(14) -0.0138(12) 0.0177(9) -0.0094(10) C8 0.0369(12) 0.0338(11) 0.0475(14) 0.0001(10) 0.0161(10) 0.0058(9) F8 0.0722(12) 0.0675(11) 0.1335(17) -0.0158(11) 0.0723(12) -0.0004(9) C9 0.0348(12) 0.0357(12) 0.0439(13) -0.0004(10) 0.0156(10) 0.0018(9) F9 0.0451(9) 0.0617(10) 0.0872(12) -0.0054(8) 0.0207(8) -0.0163(8) C10 0.0399(12) 0.0308(11) 0.0387(12) 0.0033(9) 0.0127(10) 0.0040(9) F10 0.1038(14) 0.0734(11) 0.0567(11) -0.0212(8) 0.0315(10) -0.0371(10) C11 0.0441(13) 0.0275(10) 0.0386(12) 0.0040(9) 0.0101(10) 0.0044(9) F11 0.0802(13) 0.0512(10) 0.0980(14) -0.0189(9) 0.0165(10) -0.0288(9) C12 0.0418(14) 0.0469(14) 0.0558(16) -0.0020(12) 0.0009(12) -0.0003(11) F12 0.0670(12) 0.0512(10) 0.152(2) -0.0435(11) 0.0348(12) -0.0052(9) C13 0.0579(17) 0.0507(15) 0.0491(16) -0.0122(12) -0.0001(13) 0.0013(13) F13 0.0951(14) 0.0531(10) 0.0764(12) 0.0155(8) 0.0116(10) -0.0283(9) C14 0.085(2) 0.0596(17) 0.0379(15) -0.0021(12) 0.0155(14) 0.0028(16) F14 0.0611(11) 0.0795(12) 0.0822(13) 0.0362(10) -0.0065(9) -0.0015(9) C15 0.0741(19) 0.0489(15) 0.0404(14) -0.0004(11) 0.0232(13) -0.0082(13) F15 0.0380(9) 0.175(2) 0.0766(13) 0.0264(13) 0.0232(9) 0.0215(11) C16 0.0370(13) 0.0447(14) 0.0703(18) 0.0038(13) 0.0241(13) 0.0043(11) F16 0.0700(12) 0.0811(13) 0.0802(13) -0.0232(10) -0.0195(9) 0.0168(10) C17 0.0357(12) 0.0338(11) 0.0416(13) 0.0009(9) 0.0177(10) 0.0026(9) C18 0.0439(13) 0.0302(11) 0.0518(14) 0.0020(10) 0.0210(11) 0.0015(10) C19 0.0388(12) 0.0350(11) 0.0446(13) -0.0047(10) 0.0179(10) -0.0065(10) C20 0.0335(12) 0.0414(12) 0.0414(13) -0.0001(10) 0.0123(10) -0.0040(9) C21 0.0372(12) 0.0347(11) 0.0444(13) 0.0039(10) 0.0152(10) 0.0012(9) C22 0.0310(11) 0.0310(11) 0.0430(13) 0.0003(9) 0.0160(9) 0.0021(9) C23 0.0332(11) 0.0325(11) 0.0407(12) -0.0003(9) 0.0167(9) -0.0008(9) C24 0.0364(12) 0.0338(11) 0.0454(13) -0.0038(10) 0.0127(10) -0.0031(9) C25 0.0331(11) 0.0378(12) 0.0418(13) 0.0021(10) 0.0142(10) 0.0041(9) C26 0.0307(11) 0.0296(11) 0.0452(13) 0.0012(9) 0.0130(9) -0.0018(9) C27 0.0369(12) 0.0276(10) 0.0494(14) 0.0014(10) 0.0179(10) -0.0008(9) C28 0.0391(14) 0.0481(14) 0.078(2) 0.0054(13) 0.0286(13) 0.0082(11) C29 0.0521(16) 0.0538(16) 0.080(2) -0.0063(14) 0.0381(15) 0.0017(13) C30 0.0677(18) 0.0601(17) 0.0665(19) -0.0051(14) 0.0431(15) -0.0061(14) C31 0.0537(15) 0.0456(14) 0.0480(15) 0.0030(11) 0.0219(12) 0.0039(12) C32 0.0358(13) 0.0473(14) 0.0541(16) 0.0028(12) 0.0114(11) 0.0027(11) C33 0.0427(17) 0.142(4) 0.087(3) 0.004(2) 0.0223(16) -0.015(2) C34 0.0392(16) 0.118(3) 0.084(2) -0.005(2) 0.0022(15) 0.0001(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 F1 1.5666(18) . ? S1 F2 1.5708(18) . ? S1 F5 1.5718(18) . ? S1 F4 1.5767(18) . ? S1 F3 1.5792(16) . ? S1 C3 1.807(2) . ? O1 C10 1.416(3) . ? O1 H1O 0.78(3) . ? N1 C9 1.311(3) . ? N1 C1 1.370(3) . ? C1 C2 1.411(3) . ? C1 C6 1.416(3) . ? N2 C12 1.474(3) . ? N2 C11 1.476(3) . ? N2 H2N 0.84(2) . ? C2 C3 1.361(3) . ? C2 H2A 0.9400 . ? S2 F12 1.5640(19) . ? S2 F10 1.5732(18) . ? S2 F13 1.5739(19) . ? S2 F11 1.5766(16) . ? S2 F9 1.5781(17) . ? S2 C19 1.811(2) . ? O2 C26 1.416(3) . ? O2 H2O 0.79(3) . ? C3 C4 1.404(3) . ? N3 C25 1.303(3) . ? N3 C17 1.371(3) . ? O3 C33 1.391(3) . ? O3 H3O 0.79(3) . ? C4 C5 1.368(3) . ? C4 H4A 0.9400 . ? N4 C27 1.478(3) . ? N4 C28 1.481(3) . ? N4 H4N 0.81(2) . ? O4 C34 1.387(3) . ? O4 H4O 0.88(3) . ? C5 C6 1.419(3) . ? C5 H5A 0.9400 . ? C6 C7 1.429(3) . ? F6 C16 1.320(3) . ? C7 C8 1.370(3) . ? C7 C10 1.513(3) . ? F7 C16 1.321(3) . ? C8 C9 1.403(3) . ? C8 H8A 0.9400 . ? F8 C16 1.321(3) . ? C9 C16 1.502(3) . ? C10 C11 1.538(3) . ? C10 H10A 0.9900 . ? C11 C15 1.512(4) . ? C11 H11A 0.9900 . ? C12 C13 1.515(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.515(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.525(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? F14 C32 1.311(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? F15 C32 1.302(3) . ? F16 C32 1.325(3) . ? C17 C18 1.411(3) . ? C17 C22 1.420(3) . ? C18 C19 1.362(3) . ? C18 H18A 0.9400 . ? C19 C20 1.399(3) . ? C20 C21 1.363(3) . ? C20 H20A 0.9400 . ? C21 C22 1.417(3) . ? C21 H21A 0.9400 . ? C22 C23 1.423(3) . ? C23 C24 1.364(3) . ? C23 C26 1.517(3) . ? C24 C25 1.405(3) . ? C24 H24A 0.9400 . ? C25 C32 1.514(3) . ? C26 C27 1.538(3) . ? C26 H26A 0.9900 . ? C27 C31 1.521(3) . ? C27 H27A 0.9900 . ? C28 C29 1.502(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C29 C30 1.512(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C30 C31 1.534(4) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 H34C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 S1 F2 90.17(12) . . ? F1 S1 F5 90.11(11) . . ? F2 S1 F5 175.57(9) . . ? F1 S1 F4 175.81(9) . . ? F2 S1 F4 89.69(11) . . ? F5 S1 F4 89.71(11) . . ? F1 S1 F3 88.12(9) . . ? F2 S1 F3 87.89(10) . . ? F5 S1 F3 87.70(9) . . ? F4 S1 F3 87.69(9) . . ? F1 S1 C3 92.00(10) . . ? F2 S1 C3 92.24(10) . . ? F5 S1 C3 92.17(10) . . ? F4 S1 C3 92.19(10) . . ? F3 S1 C3 179.83(12) . . ? C10 O1 H1O 110(2) . . ? C9 N1 C1 116.44(19) . . ? N1 C1 C2 116.47(19) . . ? N1 C1 C6 123.22(19) . . ? C2 C1 C6 120.31(19) . . ? C12 N2 C11 111.81(19) . . ? C12 N2 H2N 105.0(16) . . ? C11 N2 H2N 109.8(16) . . ? C3 C2 C1 119.6(2) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? F12 S2 F10 90.16(12) . . ? F12 S2 F13 91.13(12) . . ? F10 S2 F13 175.52(10) . . ? F12 S2 F11 87.85(10) . . ? F10 S2 F11 87.85(10) . . ? F13 S2 F11 87.91(10) . . ? F12 S2 F9 175.69(9) . . ? F10 S2 F9 89.15(10) . . ? F13 S2 F9 89.24(11) . . ? F11 S2 F9 87.87(10) . . ? F12 S2 C19 92.75(10) . . ? F10 S2 C19 92.19(10) . . ? F13 S2 C19 92.03(10) . . ? F11 S2 C19 179.39(12) . . ? F9 S2 C19 91.52(10) . . ? C26 O2 H2O 106(2) . . ? C2 C3 C4 121.4(2) . . ? C2 C3 S1 118.75(17) . . ? C4 C3 S1 119.87(17) . . ? C25 N3 C17 116.51(18) . . ? C33 O3 H3O 110(2) . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C27 N4 C28 111.67(19) . . ? C27 N4 H4N 107.8(16) . . ? C28 N4 H4N 105.7(16) . . ? C34 O4 H4O 112.3(18) . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C1 C6 C5 117.85(19) . . ? C1 C6 C7 117.69(19) . . ? C5 C6 C7 124.5(2) . . ? C8 C7 C6 118.11(19) . . ? C8 C7 C10 120.8(2) . . ? C6 C7 C10 121.05(19) . . ? C7 C8 C9 119.3(2) . . ? C7 C8 H8A 120.4 . . ? C9 C8 H8A 120.4 . . ? N1 C9 C8 125.3(2) . . ? N1 C9 C16 114.6(2) . . ? C8 C9 C16 120.1(2) . . ? O1 C10 C7 112.59(18) . . ? O1 C10 C11 107.34(17) . . ? C7 C10 C11 111.69(18) . . ? O1 C10 H10A 108.4 . . ? C7 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? N2 C11 C15 112.48(18) . . ? N2 C11 C10 108.08(17) . . ? C15 C11 C10 113.3(2) . . ? N2 C11 H11A 107.6 . . ? C15 C11 H11A 107.6 . . ? C10 C11 H11A 107.6 . . ? N2 C12 C13 113.5(2) . . ? N2 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N2 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 110.8(2) . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C15 110.5(2) . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C11 C15 C14 110.9(2) . . ? C11 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? F6 C16 F7 106.2(2) . . ? F6 C16 F8 106.8(2) . . ? F7 C16 F8 105.9(2) . . ? F6 C16 C9 113.3(2) . . ? F7 C16 C9 111.2(2) . . ? F8 C16 C9 112.9(2) . . ? N3 C17 C18 117.23(19) . . ? N3 C17 C22 122.6(2) . . ? C18 C17 C22 120.1(2) . . ? C19 C18 C17 119.5(2) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? C18 C19 C20 121.4(2) . . ? C18 C19 S2 119.41(18) . . ? C20 C19 S2 119.15(18) . . ? C21 C20 C19 119.9(2) . . ? C21 C20 H20A 120.0 . . ? C19 C20 H20A 120.0 . . ? C20 C21 C22 121.2(2) . . ? C20 C21 H21A 119.4 . . ? C22 C21 H21A 119.4 . . ? C21 C22 C17 117.8(2) . . ? C21 C22 C23 124.3(2) . . ? C17 C22 C23 117.9(2) . . ? C24 C23 C22 118.3(2) . . ? C24 C23 C26 120.82(19) . . ? C22 C23 C26 120.85(19) . . ? C23 C24 C25 119.0(2) . . ? C23 C24 H24A 120.5 . . ? C25 C24 H24A 120.5 . . ? N3 C25 C24 125.6(2) . . ? N3 C25 C32 115.0(2) . . ? C24 C25 C32 119.2(2) . . ? O2 C26 C23 112.05(18) . . ? O2 C26 C27 107.61(17) . . ? C23 C26 C27 112.89(18) . . ? O2 C26 H26A 108.0 . . ? C23 C26 H26A 108.0 . . ? C27 C26 H26A 108.0 . . ? N4 C27 C31 112.62(18) . . ? N4 C27 C26 107.64(17) . . ? C31 C27 C26 113.76(19) . . ? N4 C27 H27A 107.5 . . ? C31 C27 H27A 107.5 . . ? C26 C27 H27A 107.5 . . ? N4 C28 C29 113.3(2) . . ? N4 C28 H28A 108.9 . . ? C29 C28 H28A 108.9 . . ? N4 C28 H28B 108.9 . . ? C29 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C28 C29 C30 110.8(2) . . ? C28 C29 H29A 109.5 . . ? C30 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 108.1 . . ? C29 C30 C31 111.0(2) . . ? C29 C30 H30A 109.4 . . ? C31 C30 H30A 109.4 . . ? C29 C30 H30B 109.4 . . ? C31 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C27 C31 C30 110.8(2) . . ? C27 C31 H31A 109.5 . . ? C30 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 108.1 . . ? F15 C32 F14 107.6(2) . . ? F15 C32 F16 106.3(2) . . ? F14 C32 F16 105.1(2) . . ? F15 C32 C25 111.2(2) . . ? F14 C32 C25 114.0(2) . . ? F16 C32 C25 112.1(2) . . ? O3 C33 H33A 109.5 . . ? O3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O4 C34 H34A 109.5 . . ? O4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.405 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.058