# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'R. Nagarajan' _publ_contact_author_email rnsc@uohyd.ernet.in loop_ _publ_author_name T.Chaitanya 'Rajagopal Nagarajan' data_rn99_ _database_code_depnum_ccdc_archive 'CCDC 804670' #TrackingRef 'Rn99.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H24 Cl F3 N2 O3 S' _chemical_formula_sum 'C31 H24 Cl F3 N2 O3 S' _chemical_formula_weight 597.03 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1010(16) _cell_length_b 11.081(2) _cell_length_c 16.926(3) _cell_angle_alpha 100.23(3) _cell_angle_beta 99.20(3) _cell_angle_gamma 104.73(3) _cell_volume 1412.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 25.99 _exptl_crystal_description BLOCK _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9013 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9776 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0924 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4948 _reflns_number_gt 2714 _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^)+(0.0806P)^2^+1.5027P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4948 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1654 _refine_ls_R_factor_gt 0.0954 _refine_ls_wR_factor_ref 0.2240 _refine_ls_wR_factor_gt 0.1895 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.116 _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 S1 S 0.7627(2) 0.11271(16) 0.16036(11) 0.0696(5) Uani 1 1 d . . . Cl1 Cl 0.4737(3) -0.34412(17) 0.53944(13) 0.1085(8) Uani 1 1 d . . . N1 N 0.8258(5) 0.6755(4) 1.0160(3) 0.0428(11) Uani 1 1 d . . . N2 N 0.7683(5) 0.1729(4) 0.7571(3) 0.0449(11) Uani 1 1 d . . . C9 C 0.6927(6) 0.5166(5) 1.0717(3) 0.0386(12) Uani 1 1 d . . . C15 C 0.8198(6) 0.5650(4) 0.9651(3) 0.0385(12) Uani 1 1 d . . . C2 C 0.8541(6) 0.4227(5) 0.8510(3) 0.0395(12) Uani 1 1 d . . . C8 C 0.7336(6) 0.4591(4) 0.9966(3) 0.0368(12) Uani 1 1 d . . . C6 C 0.7620(6) 0.3160(5) 0.8796(3) 0.0390(12) Uani 1 1 d . . . C7 C 0.7060(6) 0.3369(5) 0.9545(3) 0.0395(12) Uani 1 1 d . . . H7 H 0.6512 0.2680 0.9747 0.047 Uiso 1 1 calc R . . C3 C 0.9101(7) 0.3928(5) 0.7768(3) 0.0488(14) Uani 1 1 d . . . H3 H 0.9782 0.4593 0.7589 0.059 Uiso 1 1 calc R . . C1 C 0.8832(6) 0.5472(5) 0.8944(3) 0.0439(13) Uani 1 1 d . . . H1 H 0.9437 0.6166 0.8764 0.053 Uiso 1 1 calc R . . C5 C 0.7206(6) 0.1948(5) 0.8295(3) 0.0429(13) Uani 1 1 d . . . H5 H 0.6571 0.1255 0.8466 0.051 Uiso 1 1 calc R . . C14 C 0.7482(6) 0.6486(4) 1.0809(3) 0.0396(12) Uani 1 1 d . . . C19 C 0.6942(7) 0.0454(5) 0.7043(3) 0.0432(13) Uani 1 1 d . . . C25 C 0.9362(7) 0.2456(6) 0.6555(4) 0.0584(16) Uani 1 1 d . . . C11 C 0.5920(7) 0.5472(5) 1.1978(3) 0.0459(13) Uani 1 1 d . . . C10 C 0.6154(6) 0.4655(5) 1.1309(3) 0.0451(13) Uani 1 1 d . . . H10 H 0.5797 0.3772 1.1256 0.054 Uiso 1 1 calc R . . O2 O 0.9012(6) 0.0575(4) 0.1535(3) 0.0858(14) Uani 1 1 d . . . C4 C 0.8691(7) 0.2725(5) 0.7308(3) 0.0475(14) Uani 1 1 d . . . C21 C 0.6791(9) -0.1737(6) 0.6741(4) 0.0669(17) Uani 1 1 d . . . H21 H 0.7146 -0.2425 0.6874 0.080 Uiso 1 1 calc R . . C13 C 0.7230(7) 0.7319(5) 1.1463(3) 0.0508(14) Uani 1 1 d . . . H13 H 0.7575 0.8202 1.1515 0.061 Uiso 1 1 calc R . . C17 C 0.8975(7) 0.8040(5) 1.0038(3) 0.0520(14) Uani 1 1 d . . . H17A H 0.9927 0.8044 0.9756 0.062 Uiso 1 1 calc R . . H17B H 0.9446 0.8634 1.0570 0.062 Uiso 1 1 calc R . . C12 C 0.6449(7) 0.6781(5) 1.2032(3) 0.0494(14) Uani 1 1 d . . . H12 H 0.6266 0.7323 1.2475 0.059 Uiso 1 1 calc R . . C24 C 0.5724(8) 0.0274(5) 0.6345(3) 0.0549(15) Uani 1 1 d . . . H24 H 0.5368 0.0962 0.6214 0.066 Uiso 1 1 calc R . . C26 C 1.0225(8) 0.1532(6) 0.6419(4) 0.0717(19) Uani 1 1 d . . . H26 H 1.0321 0.1018 0.6793 0.086 Uiso 1 1 calc R . . O3 O 0.7521(7) 0.2028(4) 0.1116(3) 0.0936(15) Uani 1 1 d . . . C20 C 0.7486(8) -0.0538(5) 0.7252(4) 0.0595(16) Uani 1 1 d . . . H20 H 0.8314 -0.0404 0.7732 0.071 Uiso 1 1 calc R . . C22 C 0.5588(9) -0.1915(5) 0.6044(4) 0.0617(17) Uani 1 1 d . . . C23 C 0.5022(8) -0.0925(6) 0.5833(4) 0.0655(17) Uani 1 1 d . . . H23 H 0.4184 -0.1062 0.5356 0.079 Uiso 1 1 calc R . . F3 F 0.9840(8) 0.2976(5) 0.2740(3) 0.1388(19) Uani 1 1 d . . . O1 O 0.6022(6) 0.0261(5) 0.1610(4) 0.130(2) Uani 1 1 d . . . C18 C 0.7628(8) 0.8488(6) 0.9548(4) 0.078(2) Uani 1 1 d . . . H18A H 0.7181 0.7917 0.9015 0.117 Uiso 1 1 calc R . . H18B H 0.8154 0.9337 0.9488 0.117 Uiso 1 1 calc R . . H18C H 0.6688 0.8496 0.9829 0.117 Uiso 1 1 calc R . . F1 F 0.7198(8) 0.2712(6) 0.2829(3) 0.171(3) Uani 1 1 d . . . F2 F 0.8525(8) 0.1428(6) 0.3179(3) 0.158(2) Uani 1 1 d . . . C30 C 0.9207(10) 0.3189(7) 0.5986(4) 0.084(2) Uani 1 1 d . . . H30 H 0.8620 0.3807 0.6063 0.101 Uiso 1 1 calc R . . C28 C 1.0790(13) 0.2109(11) 0.5192(6) 0.130(4) Uani 1 1 d . . . H28 H 1.1288 0.1998 0.4736 0.156 Uiso 1 1 calc R . . C31 C 0.8286(13) 0.2103(9) 0.2627(5) 0.092(2) Uani 1 1 d . . . C29 C 0.9923(14) 0.3012(10) 0.5299(5) 0.126(3) Uani 1 1 d . . . H29 H 0.9813 0.3505 0.4913 0.152 Uiso 1 1 calc R . . C27 C 1.0933(10) 0.1367(9) 0.5746(5) 0.103(3) Uani 1 1 d . . . H27 H 1.1516 0.0748 0.5664 0.124 Uiso 1 1 calc R . . C16 C 0.5143(8) 0.4964(6) 1.2644(4) 0.0703(18) Uani 1 1 d . . . H16A H 0.4457 0.5488 1.2849 0.105 Uiso 1 1 calc R . . H16B H 0.6063 0.4979 1.3083 0.105 Uiso 1 1 calc R . . H16C H 0.4412 0.4099 1.2425 0.105 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 0.0713(12) 0.0606(10) 0.0898(13) 0.0305(9) 0.0327(10) 0.0231(9) Cl1 0.1413(19) 0.0564(11) 0.1000(15) -0.0200(10) 0.0247(14) 0.0071(11) N1 0.040(2) 0.034(2) 0.050(3) 0.005(2) 0.012(2) 0.0038(19) N2 0.042(3) 0.049(3) 0.041(3) 0.005(2) 0.010(2) 0.011(2) C9 0.035(3) 0.046(3) 0.035(3) 0.009(2) 0.008(2) 0.010(2) C15 0.030(3) 0.038(3) 0.044(3) 0.007(2) 0.008(2) 0.005(2) C2 0.030(3) 0.043(3) 0.041(3) 0.008(2) 0.005(2) 0.006(2) C8 0.030(3) 0.040(3) 0.038(3) 0.007(2) 0.005(2) 0.010(2) C6 0.034(3) 0.042(3) 0.039(3) 0.007(2) 0.008(2) 0.010(2) C7 0.035(3) 0.041(3) 0.045(3) 0.017(2) 0.010(2) 0.008(2) C3 0.039(3) 0.053(3) 0.052(4) 0.015(3) 0.015(3) 0.003(3) C1 0.038(3) 0.044(3) 0.048(3) 0.014(3) 0.016(3) 0.003(2) C5 0.036(3) 0.043(3) 0.050(3) 0.014(3) 0.012(3) 0.007(2) C14 0.033(3) 0.039(3) 0.040(3) 0.005(2) 0.006(2) 0.003(2) C19 0.042(3) 0.040(3) 0.043(3) 0.006(2) 0.009(3) 0.005(2) C25 0.052(4) 0.067(4) 0.041(4) -0.003(3) 0.008(3) 0.001(3) C11 0.041(3) 0.059(4) 0.043(3) 0.014(3) 0.012(3) 0.021(3) C10 0.041(3) 0.042(3) 0.053(3) 0.010(3) 0.006(3) 0.015(2) O2 0.077(3) 0.087(3) 0.099(4) 0.003(3) 0.020(3) 0.046(3) C4 0.044(3) 0.056(4) 0.042(3) 0.008(3) 0.013(3) 0.012(3) C21 0.078(5) 0.050(4) 0.076(5) 0.012(3) 0.017(4) 0.027(3) C13 0.050(3) 0.048(3) 0.048(4) 0.002(3) 0.004(3) 0.014(3) C17 0.056(4) 0.038(3) 0.054(4) 0.003(3) 0.017(3) 0.002(3) C12 0.052(4) 0.058(4) 0.037(3) -0.001(3) 0.010(3) 0.019(3) C24 0.063(4) 0.050(3) 0.048(4) 0.011(3) 0.005(3) 0.014(3) C26 0.054(4) 0.076(4) 0.065(4) -0.018(3) 0.023(3) -0.001(3) O3 0.128(4) 0.080(3) 0.094(4) 0.051(3) 0.033(3) 0.040(3) C20 0.061(4) 0.057(4) 0.059(4) 0.011(3) 0.008(3) 0.020(3) C22 0.073(4) 0.048(4) 0.055(4) -0.003(3) 0.022(4) 0.008(3) C23 0.077(5) 0.058(4) 0.046(4) 0.000(3) 0.003(3) 0.005(3) F3 0.148(5) 0.102(4) 0.135(4) -0.009(3) 0.013(4) 0.018(4) O1 0.074(4) 0.109(4) 0.202(6) 0.057(4) 0.051(4) -0.013(3) C18 0.076(5) 0.058(4) 0.095(5) 0.036(4) 0.007(4) 0.004(4) F1 0.210(6) 0.215(6) 0.149(5) 0.026(4) 0.088(5) 0.148(5) F2 0.224(6) 0.207(6) 0.093(4) 0.073(4) 0.062(4) 0.109(5) C30 0.101(6) 0.096(5) 0.052(4) 0.013(4) 0.029(4) 0.014(4) C28 0.120(8) 0.152(10) 0.086(7) -0.019(7) 0.072(6) -0.015(7) C31 0.111(7) 0.109(7) 0.085(6) 0.038(5) 0.044(6) 0.055(6) C29 0.176(10) 0.139(8) 0.062(5) 0.024(5) 0.060(6) 0.019(8) C27 0.082(6) 0.114(7) 0.087(6) -0.030(5) 0.046(5) 0.002(5) C16 0.086(5) 0.083(5) 0.057(4) 0.027(3) 0.031(4) 0.034(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.409(5) . ? S1 O3 1.414(4) . ? S1 O2 1.418(4) . ? S1 C31 1.788(9) . ? Cl1 C22 1.745(6) . ? N1 C15 1.351(6) . ? N1 C14 1.390(6) . ? N1 C17 1.459(6) . ? N2 C5 1.343(6) . ? N2 C4 1.384(6) . ? N2 C19 1.450(6) . ? C9 C14 1.388(6) . ? C9 C10 1.392(7) . ? C9 C8 1.445(6) . ? C15 C1 1.379(7) . ? C15 C8 1.439(7) . ? C2 C1 1.385(7) . ? C2 C3 1.416(7) . ? C2 C6 1.435(7) . ? C8 C7 1.358(6) . ? C6 C5 1.382(6) . ? C6 C7 1.414(6) . ? C7 H7 0.9300 . ? C3 C4 1.348(7) . ? C3 H3 0.9300 . ? C1 H1 0.9300 . ? C5 H5 0.9300 . ? C14 C13 1.388(7) . ? C19 C24 1.361(7) . ? C19 C20 1.365(7) . ? C25 C30 1.377(8) . ? C25 C26 1.387(8) . ? C25 C4 1.476(7) . ? C11 C12 1.386(7) . ? C11 C10 1.390(7) . ? C11 C16 1.501(7) . ? C10 H10 0.9300 . ? C21 C22 1.355(8) . ? C21 C20 1.373(8) . ? C21 H21 0.9300 . ? C13 C12 1.375(7) . ? C13 H13 0.9300 . ? C17 C18 1.502(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C12 H12 0.9300 . ? C24 C23 1.374(7) . ? C24 H24 0.9300 . ? C26 C27 1.359(9) . ? C26 H26 0.9300 . ? C20 H20 0.9300 . ? C22 C23 1.373(8) . ? C23 H23 0.9300 . ? F3 C31 1.340(9) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? F1 C31 1.291(8) . ? F2 C31 1.318(8) . ? C30 C29 1.385(10) . ? C30 H30 0.9300 . ? C28 C27 1.362(13) . ? C28 C29 1.364(13) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C27 H27 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O3 115.6(4) . . ? O1 S1 O2 115.1(3) . . ? O3 S1 O2 114.5(3) . . ? O1 S1 C31 103.2(4) . . ? O3 S1 C31 102.8(4) . . ? O2 S1 C31 103.2(3) . . ? C15 N1 C14 109.7(4) . . ? C15 N1 C17 125.5(4) . . ? C14 N1 C17 124.7(4) . . ? C5 N2 C4 120.5(4) . . ? C5 N2 C19 117.5(4) . . ? C4 N2 C19 121.6(4) . . ? C14 C9 C10 119.7(4) . . ? C14 C9 C8 107.4(4) . . ? C10 C9 C8 132.9(5) . . ? N1 C15 C1 129.2(5) . . ? N1 C15 C8 108.8(4) . . ? C1 C15 C8 122.1(4) . . ? C1 C2 C3 123.0(5) . . ? C1 C2 C6 120.7(5) . . ? C3 C2 C6 116.4(5) . . ? C7 C8 C15 120.0(4) . . ? C7 C8 C9 134.6(5) . . ? C15 C8 C9 105.3(4) . . ? C5 C6 C7 121.7(5) . . ? C5 C6 C2 118.1(5) . . ? C7 C6 C2 120.1(4) . . ? C8 C7 C6 119.0(4) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C4 C3 C2 123.0(5) . . ? C4 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C15 C1 C2 118.0(5) . . ? C15 C1 H1 121.0 . . ? C2 C1 H1 121.0 . . ? N2 C5 C6 122.8(5) . . ? N2 C5 H5 118.6 . . ? C6 C5 H5 118.6 . . ? C9 C14 C13 121.7(5) . . ? C9 C14 N1 108.8(4) . . ? C13 C14 N1 129.5(5) . . ? C24 C19 C20 121.3(5) . . ? C24 C19 N2 119.2(5) . . ? C20 C19 N2 119.5(5) . . ? C30 C25 C26 118.6(6) . . ? C30 C25 C4 119.1(6) . . ? C26 C25 C4 122.2(6) . . ? C12 C11 C10 118.7(5) . . ? C12 C11 C16 120.0(5) . . ? C10 C11 C16 121.3(5) . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C3 C4 N2 118.9(5) . . ? C3 C4 C25 121.0(5) . . ? N2 C4 C25 120.1(5) . . ? C22 C21 C20 119.8(6) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C12 C13 C14 117.0(5) . . ? C12 C13 H13 121.5 . . ? C14 C13 H13 121.5 . . ? N1 C17 C18 112.4(4) . . ? N1 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? N1 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? C13 C12 C11 123.3(5) . . ? C13 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? C19 C24 C23 120.0(5) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C27 C26 C25 120.8(8) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C19 C20 C21 119.0(6) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C21 C22 C23 121.6(5) . . ? C21 C22 Cl1 119.3(5) . . ? C23 C22 Cl1 119.1(5) . . ? C24 C23 C22 118.3(6) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C25 C30 C29 120.3(8) . . ? C25 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C27 C28 C29 120.7(9) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.6 . . ? F1 C31 F2 107.2(7) . . ? F1 C31 F3 107.3(8) . . ? F2 C31 F3 104.4(8) . . ? F1 C31 S1 114.1(7) . . ? F2 C31 S1 111.9(6) . . ? F3 C31 S1 111.4(6) . . ? C28 C29 C30 119.5(9) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C26 C27 C28 120.1(9) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.413 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.058 data_rn38 _database_code_depnum_ccdc_archive 'CCDC 805312' #TrackingRef 'Rn38.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H29 F3 N2 O3 S' _chemical_formula_weight 590.64 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 'orthorhombic ' _symmetry_space_group_name_H-M 'P n a 21' 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' _cell_length_a 8.1925(3) _cell_length_b 16.7763(8) _cell_length_c 21.6041(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2969.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3108 _cell_measurement_theta_min 2.7613 _cell_measurement_theta_max 28.9420 _exptl_crystal_description BLOCK _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9616 _exptl_absorpt_correction_T_max 0.9805 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9034 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 29.01 _reflns_number_total 5089 _reflns_number_gt 3398 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0711P)^2^+0.8177P] 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 SHELXL _refine_ls_extinction_coef 0.0024(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.22(13) _refine_ls_number_reflns 5089 _refine_ls_number_parameters 384 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1390 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.35725(16) 0.51267(9) 0.43275(6) 0.0734(4) Uani 1 1 d . . . O1 O 0.3154(5) 0.4708(3) 0.48775(18) 0.1010(14) Uani 1 1 d . . . C33 C 0.3939(11) 0.6131(5) 0.4565(5) 0.118(3) Uani 1 1 d . . . O3 O 0.5108(8) 0.4928(4) 0.4063(3) 0.159(3) Uani 1 1 d . . . O2 O 0.2321(8) 0.5211(5) 0.3896(3) 0.174(3) Uani 1 1 d . . . F3 F 0.4978(14) 0.6169(5) 0.4983(4) 0.282(6) Uani 1 1 d . . . C23 C 0.6525(4) 0.4748(2) 0.26605(19) 0.0453(9) Uani 1 1 d . . . H23 H 0.6298 0.4741 0.3082 0.054 Uiso 1 1 calc R . . C26 C 0.2981(4) 0.5869(2) 0.2084(2) 0.0444(9) Uani 1 1 d . . . N2 N 0.7818(3) 0.43411(19) 0.24550(16) 0.0444(8) Uani 1 1 d . . . C6 C 0.3347(5) 0.5845(2) 0.14369(19) 0.0428(9) Uani 1 1 d . . . C11 C 0.9797(5) 0.3969(2) 0.1620(2) 0.0489(10) Uani 1 1 d . . . C8 C 0.5850(5) 0.5183(2) 0.16200(19) 0.0442(9) Uani 1 1 d . . . C7 C 0.4773(4) 0.5526(2) 0.1202(2) 0.0468(9) Uani 1 1 d . . . H7 H 0.5001 0.5541 0.0781 0.056 Uiso 1 1 calc R . . N1 N 0.2032(4) 0.6160(2) 0.11152(16) 0.0481(8) Uani 1 1 d . . . C27 C 0.1373(4) 0.6193(2) 0.2148(2) 0.0446(9) Uani 1 1 d . . . C20 C 0.9878(5) 0.2711(3) 0.3729(2) 0.0522(10) Uani 1 1 d . . . C9 C 0.7303(5) 0.4788(2) 0.1432(2) 0.0490(10) Uani 1 1 d . . . H9 H 0.7613 0.4817 0.1019 0.059 Uiso 1 1 calc R . . C5 C 0.0803(4) 0.6357(2) 0.1549(2) 0.0447(9) Uani 1 1 d . . . C10 C 0.8268(4) 0.4365(2) 0.1834(2) 0.0441(9) Uani 1 1 d . . . C18 C 0.8363(5) 0.2980(3) 0.2795(2) 0.0506(10) Uani 1 1 d . . . H18 H 0.7796 0.2796 0.2450 0.061 Uiso 1 1 calc R . . C2 C -0.1134(5) 0.6644(3) 0.2588(3) 0.0596(12) Uani 1 1 d . . . C24 C 0.5509(4) 0.5178(2) 0.22746(18) 0.0439(9) Uani 1 1 d . . . C25 C 0.4080(4) 0.5549(2) 0.2502(2) 0.0480(9) Uani 1 1 d . . . H25 H 0.3883 0.5577 0.2926 0.058 Uiso 1 1 calc R . . C17 C 0.8580(4) 0.3784(2) 0.2888(2) 0.0439(9) Uani 1 1 d . . . C4 C -0.0763(5) 0.6679(2) 0.1460(2) 0.0518(10) Uani 1 1 d . . . C1 C 0.0418(5) 0.6335(3) 0.2670(2) 0.0527(11) Uani 1 1 d . . . H1 H 0.0814 0.6225 0.3064 0.063 Uiso 1 1 calc R . . C3 C -0.1660(5) 0.6817(2) 0.1997(2) 0.0562(11) Uani 1 1 d . . . H3 H -0.2691 0.7043 0.1954 0.067 Uiso 1 1 calc R . . C19 C 0.9002(5) 0.2448(3) 0.3221(2) 0.0558(11) Uani 1 1 d . . . H19 H 0.8839 0.1904 0.3164 0.067 Uiso 1 1 calc R . . C30 C 0.1941(5) 0.6110(3) 0.0441(2) 0.0536(10) Uani 1 1 d . . . H30A H 0.3020 0.6200 0.0270 0.064 Uiso 1 1 calc R . . H30B H 0.1233 0.6531 0.0290 0.064 Uiso 1 1 calc R . . C22 C 0.9439(5) 0.4069(3) 0.3384(2) 0.0520(10) Uani 1 1 d . . . H22 H 0.9585 0.4614 0.3440 0.062 Uiso 1 1 calc R . . C16 C 1.1261(5) 0.4041(3) 0.1935(3) 0.0589(12) Uani 1 1 d . . . H16 H 1.1297 0.4317 0.2307 0.071 Uiso 1 1 calc R . . C12 C 0.9775(6) 0.3554(3) 0.1071(3) 0.0675(13) Uani 1 1 d . . . H12 H 0.8800 0.3498 0.0854 0.081 Uiso 1 1 calc R . . C21 C 1.0089(5) 0.3526(3) 0.3802(2) 0.0553(11) Uani 1 1 d . . . H21 H 1.0681 0.3714 0.4139 0.066 Uiso 1 1 calc R . . C28 C -0.2207(6) 0.6809(4) 0.3152(3) 0.0842(17) Uani 1 1 d . . . H28A H -0.1931 0.7320 0.3323 0.126 Uiso 1 1 calc R . . H28B H -0.2032 0.6403 0.3458 0.126 Uiso 1 1 calc R . . H28C H -0.3334 0.6809 0.3030 0.126 Uiso 1 1 calc R . . C15 C 1.2646(6) 0.3710(3) 0.1702(3) 0.0763(16) Uani 1 1 d . . . H15 H 1.3619 0.3757 0.1921 0.092 Uiso 1 1 calc R . . C31 C 0.1309(6) 0.5320(3) 0.0210(3) 0.0767(15) Uani 1 1 d . . . H31A H 0.2011 0.4900 0.0352 0.115 Uiso 1 1 calc R . . H31B H 0.1288 0.5322 -0.0235 0.115 Uiso 1 1 calc R . . H31C H 0.0225 0.5234 0.0365 0.115 Uiso 1 1 calc R . . C14 C 1.2631(7) 0.3312(3) 0.1156(4) 0.085(2) Uani 1 1 d . . . H14 H 1.3594 0.3102 0.0997 0.102 Uiso 1 1 calc R . . C13 C 1.1193(8) 0.3218(3) 0.0837(3) 0.0871(19) Uani 1 1 d . . . H13 H 1.1171 0.2933 0.0468 0.104 Uiso 1 1 calc R . . C32 C 1.0538(6) 0.2134(3) 0.4199(2) 0.0710(14) Uani 1 1 d . . . H32A H 0.9721 0.2031 0.4507 0.106 Uiso 1 1 calc R . . H32B H 1.1487 0.2359 0.4393 0.106 Uiso 1 1 calc R . . H32C H 1.0829 0.1644 0.3997 0.106 Uiso 1 1 calc R . . C29 C -0.1524(6) 0.6880(3) 0.0844(3) 0.0726(15) Uani 1 1 d . . . H29A H -0.1505 0.6418 0.0582 0.109 Uiso 1 1 calc R . . H29B H -0.0917 0.7303 0.0651 0.109 Uiso 1 1 calc R . . H29C H -0.2632 0.7048 0.0905 0.109 Uiso 1 1 calc R . . F1 F 0.4380(8) 0.6578(3) 0.4093(3) 0.166(2) Uani 1 1 d . . . F2 F 0.2647(13) 0.6455(5) 0.4785(4) 0.261(4) 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 S1 0.0916(9) 0.0867(9) 0.0418(6) 0.0025(7) -0.0008(7) -0.0161(7) O1 0.133(3) 0.120(4) 0.050(2) 0.032(2) -0.004(2) -0.021(3) C33 0.138(6) 0.109(6) 0.106(7) -0.012(5) 0.013(6) 0.006(5) O3 0.200(5) 0.122(4) 0.154(6) 0.019(4) 0.098(5) 0.050(4) O2 0.190(5) 0.241(8) 0.092(4) 0.065(5) -0.077(4) -0.126(5) F3 0.456(13) 0.188(7) 0.203(8) 0.002(6) -0.179(9) -0.120(8) C23 0.052(2) 0.052(2) 0.032(2) -0.0062(18) -0.0015(17) 0.0006(18) C26 0.049(2) 0.046(2) 0.038(2) 0.0016(19) 0.0017(18) -0.0017(16) N2 0.0439(16) 0.0516(18) 0.0379(19) -0.0008(16) -0.0040(15) -0.0003(14) C6 0.047(2) 0.043(2) 0.038(2) 0.0059(19) 0.0012(18) -0.0028(15) C11 0.054(2) 0.040(2) 0.052(3) 0.006(2) 0.011(2) -0.0008(16) C8 0.043(2) 0.051(2) 0.038(2) 0.0032(19) 0.0003(17) -0.0003(16) C7 0.051(2) 0.055(2) 0.034(2) 0.005(2) 0.0041(18) -0.0067(18) N1 0.0528(18) 0.0505(19) 0.041(2) 0.0083(16) -0.0036(16) -0.0004(14) C27 0.049(2) 0.042(2) 0.043(2) 0.0027(19) -0.0026(18) -0.0004(16) C20 0.048(2) 0.060(3) 0.049(3) 0.007(2) 0.0010(19) 0.0041(19) C9 0.050(2) 0.058(3) 0.039(2) 0.004(2) 0.0099(19) -0.0024(18) C5 0.052(2) 0.0374(19) 0.045(3) 0.0004(18) -0.0040(19) -0.0022(16) C10 0.044(2) 0.046(2) 0.042(2) 0.0005(19) 0.0054(17) -0.0051(16) C18 0.052(2) 0.054(2) 0.047(3) -0.008(2) -0.0022(19) -0.0061(17) C2 0.055(2) 0.053(2) 0.071(3) -0.007(2) 0.007(2) 0.0091(19) C24 0.043(2) 0.053(2) 0.035(2) -0.0024(18) -0.0015(16) 0.0021(16) C25 0.049(2) 0.061(2) 0.035(2) 0.002(2) -0.0013(18) 0.0041(17) C17 0.0412(19) 0.047(2) 0.043(2) -0.0002(19) 0.0002(18) 0.0024(16) C4 0.055(2) 0.044(2) 0.057(3) 0.002(2) -0.010(2) 0.0024(17) C1 0.062(3) 0.050(2) 0.046(3) -0.003(2) 0.005(2) 0.0022(18) C3 0.052(2) 0.046(2) 0.070(3) -0.001(2) -0.009(2) 0.0076(17) C19 0.063(2) 0.043(2) 0.062(3) 0.002(2) 0.003(2) 0.0018(17) C30 0.063(2) 0.057(3) 0.041(3) 0.010(2) -0.002(2) 0.0039(19) C22 0.055(2) 0.046(2) 0.055(3) -0.002(2) -0.006(2) -0.0024(18) C16 0.048(2) 0.056(2) 0.073(4) 0.010(2) 0.010(2) -0.0042(18) C12 0.070(3) 0.061(3) 0.071(4) -0.005(3) 0.016(3) -0.003(2) C21 0.053(2) 0.068(3) 0.045(3) -0.002(2) -0.005(2) 0.002(2) C28 0.078(3) 0.095(4) 0.079(4) -0.020(3) 0.017(3) 0.019(3) C15 0.060(3) 0.063(3) 0.106(5) 0.022(3) 0.018(3) 0.003(2) C31 0.093(4) 0.067(3) 0.070(4) -0.008(3) -0.015(3) -0.002(3) C14 0.073(3) 0.059(3) 0.124(6) 0.019(4) 0.043(4) 0.011(3) C13 0.105(4) 0.058(3) 0.098(5) -0.011(3) 0.042(4) 0.003(3) C32 0.074(3) 0.075(3) 0.064(4) 0.015(3) 0.006(2) 0.015(2) C29 0.076(3) 0.065(3) 0.076(4) 0.006(3) -0.017(3) 0.019(2) F1 0.250(6) 0.090(3) 0.157(5) 0.033(3) 0.048(4) -0.029(3) F2 0.366(10) 0.186(7) 0.232(9) -0.011(6) 0.155(8) 0.079(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 O2 1.392(5) . ? S1 O3 1.421(5) . ? S1 O1 1.422(4) . ? S1 C33 1.787(9) . ? C33 F3 1.243(10) . ? C33 F2 1.281(9) . ? C33 F1 1.317(9) . ? C23 N2 1.336(5) . ? C23 C24 1.381(5) . ? C23 H23 0.9300 . ? C26 C25 1.384(5) . ? C26 C6 1.431(6) . ? C26 C27 1.432(5) . ? N2 C10 1.391(5) . ? N2 C17 1.463(5) . ? C6 C7 1.381(5) . ? C6 N1 1.387(5) . ? C11 C12 1.377(7) . ? C11 C16 1.383(6) . ? C11 C10 1.491(5) . ? C8 C7 1.388(5) . ? C8 C9 1.422(5) . ? C8 C24 1.441(6) . ? C7 H7 0.9300 . ? N1 C5 1.415(5) . ? N1 C30 1.462(6) . ? C27 C1 1.393(6) . ? C27 C5 1.402(6) . ? C20 C19 1.383(6) . ? C20 C21 1.388(6) . ? C20 C32 1.503(6) . ? C9 C10 1.371(6) . ? C9 H9 0.9300 . ? C5 C4 1.406(5) . ? C18 C17 1.375(6) . ? C18 C19 1.384(6) . ? C18 H18 0.9300 . ? C2 C3 1.379(7) . ? C2 C1 1.384(6) . ? C2 C28 1.528(7) . ? C24 C25 1.414(5) . ? C25 H25 0.9300 . ? C17 C22 1.368(6) . ? C4 C3 1.393(7) . ? C4 C29 1.509(7) . ? C1 H1 0.9300 . ? C3 H3 0.9300 . ? C19 H19 0.9300 . ? C30 C31 1.508(7) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C22 C21 1.388(6) . ? C22 H22 0.9300 . ? C16 C15 1.360(7) . ? C16 H16 0.9300 . ? C12 C13 1.386(7) . ? C12 H12 0.9300 . ? C21 H21 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C15 C14 1.356(9) . ? C15 H15 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C14 C13 1.374(9) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 114.0(5) . . ? O2 S1 O1 115.6(3) . . ? O3 S1 O1 115.7(3) . . ? O2 S1 C33 102.7(5) . . ? O3 S1 C33 100.8(4) . . ? O1 S1 C33 105.4(4) . . ? F3 C33 F2 106.0(10) . . ? F3 C33 F1 110.3(9) . . ? F2 C33 F1 105.8(8) . . ? F3 C33 S1 111.8(7) . . ? F2 C33 S1 111.6(7) . . ? F1 C33 S1 111.1(6) . . ? N2 C23 C24 123.0(4) . . ? N2 C23 H23 118.5 . . ? C24 C23 H23 118.5 . . ? C25 C26 C6 119.4(4) . . ? C25 C26 C27 133.1(4) . . ? C6 C26 C27 107.3(4) . . ? C23 N2 C10 121.0(3) . . ? C23 N2 C17 116.9(3) . . ? C10 N2 C17 121.5(3) . . ? C7 C6 N1 128.4(4) . . ? C7 C6 C26 123.1(4) . . ? N1 C6 C26 108.5(3) . . ? C12 C11 C16 118.6(4) . . ? C12 C11 C10 118.8(4) . . ? C16 C11 C10 122.5(4) . . ? C7 C8 C9 122.7(4) . . ? C7 C8 C24 121.2(4) . . ? C9 C8 C24 116.1(4) . . ? C6 C7 C8 117.4(4) . . ? C6 C7 H7 121.3 . . ? C8 C7 H7 121.3 . . ? C6 N1 C5 108.0(3) . . ? C6 N1 C30 121.2(3) . . ? C5 N1 C30 129.7(3) . . ? C1 C27 C5 121.7(3) . . ? C1 C27 C26 131.2(4) . . ? C5 C27 C26 107.0(4) . . ? C19 C20 C21 117.9(4) . . ? C19 C20 C32 121.2(4) . . ? C21 C20 C32 120.8(4) . . ? C10 C9 C8 122.9(4) . . ? C10 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? C27 C5 C4 120.4(4) . . ? C27 C5 N1 109.2(3) . . ? C4 C5 N1 130.4(4) . . ? C9 C10 N2 118.2(4) . . ? C9 C10 C11 121.2(4) . . ? N2 C10 C11 120.5(4) . . ? C17 C18 C19 119.0(4) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C3 C2 C1 119.0(4) . . ? C3 C2 C28 121.3(4) . . ? C1 C2 C28 119.7(5) . . ? C23 C24 C25 121.2(4) . . ? C23 C24 C8 118.6(4) . . ? C25 C24 C8 119.9(4) . . ? C26 C25 C24 118.9(4) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? C22 C17 C18 121.7(4) . . ? C22 C17 N2 119.8(4) . . ? C18 C17 N2 118.5(4) . . ? C3 C4 C5 115.6(4) . . ? C3 C4 C29 118.7(4) . . ? C5 C4 C29 125.7(4) . . ? C2 C1 C27 118.5(4) . . ? C2 C1 H1 120.8 . . ? C27 C1 H1 120.8 . . ? C2 C3 C4 124.8(4) . . ? C2 C3 H3 117.6 . . ? C4 C3 H3 117.6 . . ? C20 C19 C18 121.2(4) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? N1 C30 C31 113.4(4) . . ? N1 C30 H30A 108.9 . . ? C31 C30 H30A 108.9 . . ? N1 C30 H30B 108.9 . . ? C31 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C17 C22 C21 118.4(4) . . ? C17 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? C15 C16 C11 120.4(5) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C11 C12 C13 120.6(5) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C20 C21 C22 121.7(4) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C2 C28 H28A 109.5 . . ? C2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C14 C15 C16 121.0(6) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C15 C14 C13 120.0(5) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C13 C12 119.3(6) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C20 C32 H32A 109.5 . . ? C20 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C20 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C4 C29 H29A 109.5 . . ? C4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.878 _refine_diff_density_max 0.293 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.041