# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_z _database_code_depnum_ccdc_archive 'CCDC 887378' #TrackingRef 'web_deposit_cif_file_0_JunZhang_1340017342.Z.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H33 F3 N2 O3 S' _chemical_formula_weight 546.63 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.6191(11) _cell_length_b 14.5312(14) _cell_length_c 17.0220(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2874.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9284 _exptl_absorpt_correction_T_max 0.9648 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 32907 _diffrn_reflns_av_R_equivalents 0.1089 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5056 _reflns_number_gt 2535 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1550P)^2^+1.1830P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(3) _refine_ls_number_reflns 5056 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1654 _refine_ls_R_factor_gt 0.0858 _refine_ls_wR_factor_ref 0.2978 _refine_ls_wR_factor_gt 0.2280 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.3994(2) 0.54720(17) 0.03983(17) 0.1169(9) Uani 1 1 d . . . O1 O 0.3307(8) 0.6137(6) 0.0079(9) 0.229(6) Uani 1 1 d . . . O2 O 0.3677(15) 0.5155(8) 0.1151(5) 0.295(9) Uani 1 1 d . . . O3 O 0.5204(6) 0.5683(6) 0.0351(4) 0.154(3) Uani 1 1 d . . . F1 F 0.4122(10) 0.4597(8) -0.0869(5) 0.234(5) Uani 1 1 d . . . F2 F 0.4326(8) 0.3757(5) 0.0110(7) 0.215(4) Uani 1 1 d . . . F3 F 0.2697(6) 0.4211(5) -0.0178(5) 0.181(3) Uani 1 1 d . . . C29 C 0.3785(11) 0.4466(11) -0.0144(6) 0.140(4) Uani 1 1 d . . . N1 N 0.0611(4) 0.7054(4) 0.1378(3) 0.0661(14) Uani 1 1 d . . . N2 N -0.0088(5) 0.6251(4) 0.0395(3) 0.0706(14) Uani 1 1 d . . . C1 C 0.1410(6) 0.7348(4) 0.1967(4) 0.0680(17) Uani 1 1 d . . . C2 C 0.1835(7) 0.6723(5) 0.2493(5) 0.089(2) Uani 1 1 d . . . C3 C 0.2546(8) 0.7046(7) 0.3102(5) 0.099(3) Uani 1 1 d . . . H3A H 0.2874 0.6627 0.3449 0.119 Uiso 1 1 calc R . . C4 C 0.2767(8) 0.7973(7) 0.3195(6) 0.107(3) Uani 1 1 d . . . C5 C 0.2331(8) 0.8570(6) 0.2662(5) 0.098(3) Uani 1 1 d . . . H5A H 0.2485 0.9194 0.2722 0.118 Uiso 1 1 calc R . . C6 C 0.1669(7) 0.8293(5) 0.2033(5) 0.085(2) Uani 1 1 d . . . C7 C 0.3476(12) 0.8288(8) 0.3892(7) 0.161(5) Uani 1 1 d . . . H7A H 0.3693 0.7764 0.4202 0.242 Uiso 1 1 calc R . . H7B H 0.3030 0.8704 0.4207 0.242 Uiso 1 1 calc R . . H7C H 0.4156 0.8596 0.3708 0.242 Uiso 1 1 calc R . . C8 C 0.1321(9) 0.8982(5) 0.1455(6) 0.120(3) Uani 1 1 d . . . H8A H 0.1588 0.9577 0.1618 0.179 Uiso 1 1 calc R . . H8B H 0.0497 0.8989 0.1413 0.179 Uiso 1 1 calc R . . H8C H 0.1650 0.8832 0.0953 0.179 Uiso 1 1 calc R . . C9 C 0.1703(9) 0.5693(5) 0.2407(5) 0.104(3) Uani 1 1 d . . . H9A H 0.2063 0.5391 0.2844 0.157 Uiso 1 1 calc R . . H9B H 0.2062 0.5496 0.1928 0.157 Uiso 1 1 calc R . . H9C H 0.0900 0.5538 0.2395 0.157 Uiso 1 1 calc R . . C10 C -0.0102(6) 0.5661(4) -0.0284(4) 0.0649(15) Uani 1 1 d . . . C11 C -0.0095(6) 0.6046(5) -0.1014(4) 0.0790(19) Uani 1 1 d . . . C12 C -0.0149(7) 0.5463(6) -0.1663(5) 0.090(2) Uani 1 1 d . . . H12A H -0.0119 0.5717 -0.2164 0.108 Uiso 1 1 calc R . . C13 C -0.0245(6) 0.4520(6) -0.1584(5) 0.083(2) Uani 1 1 d . . . C14 C -0.0249(7) 0.4151(5) -0.0831(5) 0.086(2) Uani 1 1 d . . . H14A H -0.0310 0.3516 -0.0772 0.103 Uiso 1 1 calc R . . C15 C -0.0166(6) 0.4693(4) -0.0167(4) 0.0732(18) Uani 1 1 d . . . C16 C 0.0065(12) 0.7058(5) -0.1124(5) 0.127(4) Uani 1 1 d . . . H16A H 0.0089 0.7355 -0.0620 0.191 Uiso 1 1 calc R . . H16B H -0.0565 0.7301 -0.1425 0.191 Uiso 1 1 calc R . . H16C H 0.0774 0.7169 -0.1398 0.191 Uiso 1 1 calc R . . C17 C -0.0383(8) 0.3931(7) -0.2306(5) 0.114(3) Uani 1 1 d . . . H17A H -0.0364 0.4313 -0.2766 0.171 Uiso 1 1 calc R . . H17B H -0.1106 0.3612 -0.2283 0.171 Uiso 1 1 calc R . . H17C H 0.0233 0.3491 -0.2330 0.171 Uiso 1 1 calc R . . C18 C -0.0114(10) 0.4258(6) 0.0629(5) 0.118(3) Uani 1 1 d . . . H18A H -0.0170 0.3602 0.0577 0.177 Uiso 1 1 calc R . . H18B H -0.0740 0.4480 0.0944 0.177 Uiso 1 1 calc R . . H18C H 0.0603 0.4414 0.0877 0.177 Uiso 1 1 calc R . . C19 C -0.0620(6) 0.7392(4) 0.1320(4) 0.0743(18) Uani 1 1 d . . . H19A H -0.0600 0.8016 0.1103 0.089 Uiso 1 1 calc R . . C20 C -0.1132(7) 0.6748(5) 0.0679(4) 0.083(2) Uani 1 1 d . . . H20A H -0.1429 0.7129 0.0249 0.099 Uiso 1 1 calc R . . C21 C 0.0806(7) 0.6459(4) 0.0831(4) 0.0724(18) Uani 1 1 d . . . H21A H 0.1527 0.6197 0.0752 0.087 Uiso 1 1 calc R . . C22 C -0.2069(7) 0.6095(7) 0.0937(6) 0.116(3) Uani 1 1 d . . . H22A H -0.2329 0.5743 0.0493 0.174 Uiso 1 1 calc R . . H22B H -0.2701 0.6439 0.1150 0.174 Uiso 1 1 calc R . . H22C H -0.1773 0.5686 0.1331 0.174 Uiso 1 1 calc R . . C23 C -0.1227(6) 0.7440(5) 0.2105(4) 0.0734(18) Uani 1 1 d . . . C24 C -0.1104(8) 0.6774(6) 0.2691(5) 0.100(2) Uani 1 1 d . . . H24A H -0.0645 0.6261 0.2599 0.120 Uiso 1 1 calc R . . C25 C -0.1650(10) 0.6869(8) 0.3396(6) 0.120(3) Uani 1 1 d . . . H25A H -0.1546 0.6434 0.3790 0.144 Uiso 1 1 calc R . . C26 C -0.2346(11) 0.7603(10) 0.3515(7) 0.129(4) Uani 1 1 d . . . H26A H -0.2727 0.7658 0.3993 0.155 Uiso 1 1 calc R . . C27 C -0.2501(10) 0.8247(7) 0.2970(8) 0.123(4) Uani 1 1 d . . . H27A H -0.2995 0.8738 0.3068 0.147 Uiso 1 1 calc R . . C28 C -0.1920(8) 0.8188(5) 0.2245(6) 0.101(3) Uani 1 1 d . . . H28B H -0.2005 0.8647 0.1868 0.121 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 0.123(2) 0.0856(14) 0.142(2) -0.0010(14) 0.0440(16) -0.0110(15) O1 0.140(7) 0.107(5) 0.439(18) 0.071(8) -0.004(9) 0.015(5) O2 0.49(2) 0.281(13) 0.111(6) -0.064(7) 0.121(9) -0.245(15) O3 0.093(4) 0.205(7) 0.164(6) -0.041(6) 0.015(4) -0.059(5) F1 0.292(11) 0.277(10) 0.132(5) -0.051(6) 0.034(6) -0.125(9) F2 0.208(8) 0.125(5) 0.312(11) -0.028(6) -0.089(8) 0.058(5) F3 0.124(5) 0.189(6) 0.230(7) -0.004(5) -0.004(5) -0.062(5) C29 0.142(10) 0.196(12) 0.081(7) 0.021(7) -0.012(6) -0.049(10) N1 0.068(3) 0.067(3) 0.063(3) -0.011(3) 0.004(3) 0.006(3) N2 0.069(3) 0.073(3) 0.070(3) -0.005(3) -0.001(3) 0.008(3) C1 0.072(4) 0.061(4) 0.071(4) -0.001(3) 0.002(4) 0.008(3) C2 0.094(5) 0.083(5) 0.090(5) -0.002(4) 0.006(5) 0.012(4) C3 0.108(6) 0.110(7) 0.080(5) -0.006(5) -0.019(5) 0.022(5) C4 0.098(6) 0.110(7) 0.113(7) -0.021(6) -0.024(5) -0.003(6) C5 0.101(6) 0.078(5) 0.116(7) -0.026(5) -0.028(5) -0.004(4) C6 0.089(5) 0.071(5) 0.094(5) -0.001(4) 0.000(4) 0.000(4) C7 0.181(12) 0.148(9) 0.155(9) -0.046(8) -0.075(9) 0.021(9) C8 0.137(8) 0.066(5) 0.155(8) 0.024(5) -0.021(7) -0.016(5) C9 0.147(7) 0.064(5) 0.103(6) 0.007(4) 0.001(5) 0.025(4) C10 0.075(4) 0.060(4) 0.060(4) -0.005(3) 0.011(3) 0.003(3) C11 0.080(5) 0.076(4) 0.081(5) -0.004(4) 0.014(4) -0.007(4) C12 0.094(5) 0.095(5) 0.082(5) -0.017(4) 0.016(4) -0.009(5) C13 0.070(4) 0.093(5) 0.085(5) -0.029(4) 0.003(4) 0.008(4) C14 0.089(5) 0.074(4) 0.095(6) -0.009(4) 0.008(4) 0.010(4) C15 0.074(4) 0.072(4) 0.074(4) -0.002(4) 0.005(4) 0.003(3) C16 0.202(11) 0.077(5) 0.103(6) 0.012(4) 0.027(7) 0.000(6) C17 0.104(7) 0.123(7) 0.115(6) -0.045(6) -0.005(5) 0.007(5) C18 0.156(9) 0.093(5) 0.104(6) 0.015(5) -0.008(6) 0.006(6) C19 0.079(4) 0.062(4) 0.082(5) -0.009(3) 0.004(4) 0.006(3) C20 0.084(5) 0.086(5) 0.078(5) -0.019(4) -0.004(4) 0.006(4) C21 0.081(5) 0.061(4) 0.075(5) 0.003(4) 0.001(4) 0.009(3) C22 0.080(6) 0.128(7) 0.140(8) -0.045(6) 0.009(5) -0.016(5) C23 0.080(5) 0.061(4) 0.080(5) -0.016(4) 0.002(4) 0.005(4) C24 0.094(6) 0.102(6) 0.104(6) -0.006(5) 0.012(5) 0.010(5) C25 0.125(8) 0.126(8) 0.108(8) 0.008(6) 0.025(6) -0.007(7) C26 0.137(9) 0.133(9) 0.118(8) -0.045(8) 0.045(7) -0.035(8) C27 0.128(8) 0.077(6) 0.163(10) -0.056(7) 0.053(8) -0.001(6) C28 0.112(7) 0.060(4) 0.129(7) -0.029(5) 0.019(5) 0.007(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 1.366(9) . ? S1 O2 1.411(8) . ? S1 O3 1.442(7) . ? S1 C29 1.745(14) . ? F1 C29 1.308(11) . ? F2 C29 1.282(15) . ? F3 C29 1.319(12) . ? N1 C21 1.289(8) . ? N1 C1 1.433(8) . ? N1 C19 1.515(8) . ? N2 C21 1.312(9) . ? N2 C10 1.439(8) . ? N2 C20 1.492(9) . ? C1 C2 1.367(10) . ? C1 C6 1.410(10) . ? C2 C3 1.408(12) . ? C2 C9 1.511(11) . ? C3 C4 1.381(13) . ? C3 H3A 0.9300 . ? C4 C5 1.354(12) . ? C4 C7 1.514(13) . ? C5 C6 1.378(11) . ? C5 H5A 0.9300 . ? C6 C8 1.460(11) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.362(9) . ? C10 C15 1.422(9) . ? C11 C12 1.394(10) . ? C11 C16 1.495(11) . ? C12 C13 1.382(11) . ? C12 H12A 0.9300 . ? C13 C14 1.390(10) . ? C13 C17 1.506(10) . ? C14 C15 1.381(10) . ? C14 H14A 0.9300 . ? C15 C18 1.497(10) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C23 1.512(9) . ? C19 C20 1.555(9) . ? C19 H19A 0.9800 . ? C20 C22 1.510(11) . ? C20 H20A 0.9800 . ? C21 H21A 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C28 1.374(10) . ? C23 C24 1.396(11) . ? C24 C25 1.364(12) . ? C24 H24A 0.9300 . ? C25 C26 1.353(15) . ? C25 H25A 0.9300 . ? C26 C27 1.331(15) . ? C26 H26A 0.9300 . ? C27 C28 1.410(14) . ? C27 H27A 0.9300 . ? C28 H28B 0.9300 . ? 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 O2 116.1(10) . . ? O1 S1 O3 113.4(6) . . ? O2 S1 O3 112.0(8) . . ? O1 S1 C29 107.5(7) . . ? O2 S1 C29 99.8(6) . . ? O3 S1 C29 106.5(5) . . ? F2 C29 F1 106.7(14) . . ? F2 C29 F3 105.0(11) . . ? F1 C29 F3 106.6(9) . . ? F2 C29 S1 115.3(7) . . ? F1 C29 S1 109.6(10) . . ? F3 C29 S1 113.1(11) . . ? C21 N1 C1 126.2(6) . . ? C21 N1 C19 109.7(6) . . ? C1 N1 C19 124.1(5) . . ? C21 N2 C10 126.9(6) . . ? C21 N2 C20 110.4(5) . . ? C10 N2 C20 122.6(5) . . ? C2 C1 C6 121.2(7) . . ? C2 C1 N1 119.6(6) . . ? C6 C1 N1 118.9(6) . . ? C1 C2 C3 118.2(7) . . ? C1 C2 C9 124.0(8) . . ? C3 C2 C9 117.5(8) . . ? C4 C3 C2 121.3(8) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C5 C4 C3 118.6(8) . . ? C5 C4 C7 122.4(9) . . ? C3 C4 C7 119.0(10) . . ? C4 C5 C6 122.9(8) . . ? C4 C5 H5A 118.5 . . ? C6 C5 H5A 118.5 . . ? C5 C6 C1 117.7(7) . . ? C5 C6 C8 118.5(7) . . ? C1 C6 C8 123.7(7) . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 122.3(6) . . ? C11 C10 N2 119.2(5) . . ? C15 C10 N2 118.5(6) . . ? C10 C11 C12 118.3(6) . . ? C10 C11 C16 121.3(7) . . ? C12 C11 C16 120.3(7) . . ? C13 C12 C11 122.0(7) . . ? C13 C12 H12A 119.0 . . ? C11 C12 H12A 119.0 . . ? C12 C13 C14 118.2(7) . . ? C12 C13 C17 119.6(8) . . ? C14 C13 C17 122.2(8) . . ? C15 C14 C13 122.3(7) . . ? C15 C14 H14A 118.9 . . ? C13 C14 H14A 118.9 . . ? C14 C15 C10 117.0(6) . . ? C14 C15 C18 120.2(6) . . ? C10 C15 C18 122.8(6) . . ? 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 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C23 C19 N1 113.4(6) . . ? C23 C19 C20 118.0(6) . . ? N1 C19 C20 102.2(5) . . ? C23 C19 H19A 107.6 . . ? N1 C19 H19A 107.6 . . ? C20 C19 H19A 107.6 . . ? N2 C20 C22 112.1(6) . . ? N2 C20 C19 102.0(5) . . ? C22 C20 C19 116.7(6) . . ? N2 C20 H20A 108.6 . . ? C22 C20 H20A 108.6 . . ? C19 C20 H20A 108.6 . . ? N1 C21 N2 115.0(6) . . ? N1 C21 H21A 122.5 . . ? N2 C21 H21A 122.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 118.9(7) . . ? C28 C23 C19 117.6(7) . . ? C24 C23 C19 123.5(6) . . ? C25 C24 C23 120.7(9) . . ? C25 C24 H24A 119.6 . . ? C23 C24 H24A 119.6 . . ? C26 C25 C24 119.3(10) . . ? C26 C25 H25A 120.3 . . ? C24 C25 H25A 120.3 . . ? C27 C26 C25 122.0(10) . . ? C27 C26 H26A 119.0 . . ? C25 C26 H26A 119.0 . . ? C26 C27 C28 120.2(9) . . ? C26 C27 H27A 119.9 . . ? C28 C27 H27A 119.9 . . ? C23 C28 C27 118.7(9) . . ? C23 C28 H28B 120.6 . . ? C27 C28 H28B 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C29 F2 -176.3(10) . . . . ? O2 S1 C29 F2 -54.8(13) . . . . ? O3 S1 C29 F2 61.8(11) . . . . ? O1 S1 C29 F1 63.2(12) . . . . ? O2 S1 C29 F1 -175.2(12) . . . . ? O3 S1 C29 F1 -58.6(12) . . . . ? O1 S1 C29 F3 -55.6(10) . . . . ? O2 S1 C29 F3 66.0(12) . . . . ? O3 S1 C29 F3 -177.4(8) . . . . ? C21 N1 C1 C2 -62.0(9) . . . . ? C19 N1 C1 C2 116.6(7) . . . . ? C21 N1 C1 C6 123.1(8) . . . . ? C19 N1 C1 C6 -58.3(9) . . . . ? C6 C1 C2 C3 -0.3(11) . . . . ? N1 C1 C2 C3 -175.0(7) . . . . ? C6 C1 C2 C9 -172.9(8) . . . . ? N1 C1 C2 C9 12.3(11) . . . . ? C1 C2 C3 C4 3.2(13) . . . . ? C9 C2 C3 C4 176.3(9) . . . . ? C2 C3 C4 C5 -3.3(15) . . . . ? C2 C3 C4 C7 176.1(9) . . . . ? C3 C4 C5 C6 0.5(15) . . . . ? C7 C4 C5 C6 -178.9(10) . . . . ? C4 C5 C6 C1 2.3(13) . . . . ? C4 C5 C6 C8 -174.9(10) . . . . ? C2 C1 C6 C5 -2.3(11) . . . . ? N1 C1 C6 C5 172.4(7) . . . . ? C2 C1 C6 C8 174.7(8) . . . . ? N1 C1 C6 C8 -10.5(12) . . . . ? C21 N2 C10 C11 -100.3(8) . . . . ? C20 N2 C10 C11 77.3(9) . . . . ? C21 N2 C10 C15 82.1(8) . . . . ? C20 N2 C10 C15 -100.3(7) . . . . ? C15 C10 C11 C12 -0.3(11) . . . . ? N2 C10 C11 C12 -177.8(6) . . . . ? C15 C10 C11 C16 -175.2(8) . . . . ? N2 C10 C11 C16 7.2(12) . . . . ? C10 C11 C12 C13 2.1(11) . . . . ? C16 C11 C12 C13 177.1(9) . . . . ? C11 C12 C13 C14 -2.1(12) . . . . ? C11 C12 C13 C17 175.7(7) . . . . ? C12 C13 C14 C15 0.3(11) . . . . ? C17 C13 C14 C15 -177.5(7) . . . . ? C13 C14 C15 C10 1.4(11) . . . . ? C13 C14 C15 C18 -176.9(8) . . . . ? C11 C10 C15 C14 -1.4(10) . . . . ? N2 C10 C15 C14 176.2(6) . . . . ? C11 C10 C15 C18 176.8(8) . . . . ? N2 C10 C15 C18 -5.6(10) . . . . ? C21 N1 C19 C23 135.5(6) . . . . ? C1 N1 C19 C23 -43.3(8) . . . . ? C21 N1 C19 C20 7.4(7) . . . . ? C1 N1 C19 C20 -171.4(6) . . . . ? C21 N2 C20 C22 -118.9(7) . . . . ? C10 N2 C20 C22 63.1(8) . . . . ? C21 N2 C20 C19 6.7(7) . . . . ? C10 N2 C20 C19 -171.2(5) . . . . ? C23 C19 C20 N2 -133.1(6) . . . . ? N1 C19 C20 N2 -8.0(6) . . . . ? C23 C19 C20 C22 -10.6(10) . . . . ? N1 C19 C20 C22 114.6(7) . . . . ? C1 N1 C21 N2 175.2(6) . . . . ? C19 N1 C21 N2 -3.6(8) . . . . ? C10 N2 C21 N1 175.6(6) . . . . ? C20 N2 C21 N1 -2.3(8) . . . . ? N1 C19 C23 C28 139.1(7) . . . . ? C20 C19 C23 C28 -101.5(8) . . . . ? N1 C19 C23 C24 -39.9(9) . . . . ? C20 C19 C23 C24 79.5(9) . . . . ? C28 C23 C24 C25 -0.8(13) . . . . ? C19 C23 C24 C25 178.2(8) . . . . ? C23 C24 C25 C26 2.1(15) . . . . ? C24 C25 C26 C27 -1.2(17) . . . . ? C25 C26 C27 C28 -1.0(17) . . . . ? C24 C23 C28 C27 -1.3(12) . . . . ? C19 C23 C28 C27 179.7(8) . . . . ? C26 C27 C28 C23 2.2(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.565 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.052 data_z2 _database_code_depnum_ccdc_archive 'CCDC 887379' #TrackingRef 'web_deposit_cif_file_1_JunZhang_1340017342.z1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H35 F3 N2 O3 S' _chemical_formula_weight 560.66 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.5154(5) _cell_length_b 14.5123(6) _cell_length_c 17.4192(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2911.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9435 _exptl_absorpt_correction_T_max 0.9806 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 34247 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5127 _reflns_number_gt 3165 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1540P)^2^+1.1353P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 5127 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.2624 _refine_ls_wR_factor_gt 0.2218 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.09358(17) 0.02964(13) 0.95999(12) 0.0869(6) Uani 1 1 d . . . O1 O 0.1099(12) -0.0121(7) 0.8888(4) 0.246(7) Uani 1 1 d . . . O2 O 0.1706(9) 0.0892(7) 0.9879(10) 0.267(8) Uani 1 1 d . . . O3 O -0.0161(6) 0.0661(6) 0.9715(4) 0.146(3) Uani 1 1 d . . . F1 F 0.0491(10) -0.1351(6) 1.0015(5) 0.211(4) Uani 1 1 d . . . F2 F 0.2111(7) -0.1025(6) 1.0210(4) 0.183(3) Uani 1 1 d . . . F3 F 0.0785(7) -0.0496(5) 1.0920(3) 0.156(3) Uani 1 1 d . . . C30 C 0.1048(10) -0.0632(6) 1.0245(4) 0.102(3) Uani 1 1 d . . . N1 N 0.5184(4) 0.1197(3) 0.9637(3) 0.0550(10) Uani 1 1 d . . . N2 N 0.4522(4) 0.1940(3) 0.8636(2) 0.0539(11) Uani 1 1 d . . . C1 C 0.5188(4) 0.0641(4) 1.0332(3) 0.0513(12) Uani 1 1 d . . . C2 C 0.5254(5) 0.1086(4) 1.1040(3) 0.0565(13) Uani 1 1 d . . . C3 C 0.5316(5) 0.0541(4) 1.1680(4) 0.0668(15) Uani 1 1 d . . . H3A H 0.5354 0.0827 1.2157 0.080 Uiso 1 1 calc R . . C4 C 0.5325(5) -0.0414(4) 1.1657(4) 0.0660(16) Uani 1 1 d . . . C5 C 0.5217(6) -0.0814(4) 1.0943(4) 0.0681(16) Uani 1 1 d . . . H5A H 0.5197 -0.1454 1.0912 0.082 Uiso 1 1 calc R . . C6 C 0.5135(5) -0.0315(4) 1.0272(3) 0.0620(14) Uani 1 1 d . . . C7 C 0.5257(7) 0.2130(4) 1.1125(4) 0.0783(18) Uani 1 1 d . . . H7A H 0.5298 0.2288 1.1660 0.117 Uiso 1 1 calc R . . H7B H 0.4557 0.2378 1.0909 0.117 Uiso 1 1 calc R . . H7C H 0.5916 0.2382 1.0862 0.117 Uiso 1 1 calc R . . C8 C 0.5415(7) -0.0976(5) 1.2379(4) 0.088(2) Uani 1 1 d . . . H8A H 0.5422 -0.1620 1.2250 0.133 Uiso 1 1 calc R . . H8B H 0.4760 -0.0848 1.2703 0.133 Uiso 1 1 calc R . . H8C H 0.6118 -0.0821 1.2645 0.133 Uiso 1 1 calc R . . C9 C 0.4927(7) -0.0809(5) 0.9526(4) 0.086(2) Uani 1 1 d . . . H9A H 0.4935 -0.1462 0.9613 0.129 Uiso 1 1 calc R . . H9B H 0.5528 -0.0650 0.9168 0.129 Uiso 1 1 calc R . . H9C H 0.4187 -0.0630 0.9322 0.129 Uiso 1 1 calc R . . C10 C 0.3721(4) 0.2254(4) 0.8060(3) 0.0495(12) Uani 1 1 d . . . C11 C 0.3177(5) 0.1599(4) 0.7593(3) 0.0573(14) Uani 1 1 d . . . C12 C 0.2481(6) 0.1924(5) 0.7006(4) 0.0727(17) Uani 1 1 d . . . H12A H 0.2125 0.1500 0.6682 0.087 Uiso 1 1 calc R . . C13 C 0.2296(6) 0.2840(5) 0.6884(4) 0.0749(17) Uani 1 1 d . . . C14 C 0.2819(5) 0.3470(5) 0.7370(4) 0.0679(16) Uani 1 1 d . . . H14A H 0.2680 0.4095 0.7296 0.082 Uiso 1 1 calc R . . C15 C 0.3541(4) 0.3200(4) 0.7963(3) 0.0548(13) Uani 1 1 d . . . C16 C 0.3348(7) 0.0568(4) 0.7690(4) 0.0759(18) Uani 1 1 d . . . H16A H 0.2903 0.0247 0.7308 0.114 Uiso 1 1 calc R . . H16B H 0.3092 0.0386 0.8192 0.114 Uiso 1 1 calc R . . H16C H 0.4155 0.0421 0.7631 0.114 Uiso 1 1 calc R . . C17 C 0.1550(8) 0.3158(7) 0.6218(5) 0.120(3) Uani 1 1 d . . . H17A H 0.1264 0.2631 0.5944 0.180 Uiso 1 1 calc R . . H17B H 0.2007 0.3532 0.5878 0.180 Uiso 1 1 calc R . . H17C H 0.0908 0.3511 0.6409 0.180 Uiso 1 1 calc R . . C18 C 0.4085(6) 0.3903(4) 0.8475(4) 0.0754(17) Uani 1 1 d . . . H18A H 0.3861 0.4509 0.8310 0.113 Uiso 1 1 calc R . . H18B H 0.4915 0.3846 0.8451 0.113 Uiso 1 1 calc R . . H18C H 0.3830 0.3806 0.8993 0.113 Uiso 1 1 calc R . . C19 C 0.6368(5) 0.2348(4) 0.7914(3) 0.0594(14) Uani 1 1 d . . . C20 C 0.7158(6) 0.3080(4) 0.7883(4) 0.0759(18) Uani 1 1 d . . . H20A H 0.7303 0.3440 0.8314 0.091 Uiso 1 1 calc R . . C21 C 0.7716(7) 0.3255(6) 0.7200(7) 0.105(3) Uani 1 1 d . . . H21A H 0.8243 0.3739 0.7177 0.125 Uiso 1 1 calc R . . C22 C 0.7528(8) 0.2758(8) 0.6574(6) 0.102(3) Uani 1 1 d . . . H22A H 0.7928 0.2889 0.6124 0.123 Uiso 1 1 calc R . . C23 C 0.6748(7) 0.2058(7) 0.6593(4) 0.101(3) Uani 1 1 d . . . H23A H 0.6615 0.1712 0.6152 0.121 Uiso 1 1 calc R . . C24 C 0.6147(6) 0.1851(5) 0.7262(4) 0.0813(19) Uani 1 1 d . . . H24A H 0.5599 0.1380 0.7267 0.098 Uiso 1 1 calc R . . C25 C 0.6275(5) 0.1498(4) 0.9234(3) 0.0610(14) Uani 1 1 d . . . C26 C 0.5780(5) 0.2196(5) 0.8671(4) 0.0759(18) Uani 1 1 d . . . H26A H 0.5809 0.2791 0.8937 0.091 Uiso 1 1 calc R . . C27 C 0.4266(5) 0.1424(3) 0.9239(3) 0.0536(13) Uani 1 1 d . . . H27A H 0.3516 0.1242 0.9365 0.064 Uiso 1 1 calc R . . C28 C 0.7218(7) 0.1845(9) 0.9750(6) 0.143(5) Uani 1 1 d . . . H28A H 0.6942 0.2370 1.0031 0.215 Uiso 1 1 calc R . . H28B H 0.7879 0.2019 0.9447 0.215 Uiso 1 1 calc R . . H28C H 0.7437 0.1367 1.0103 0.215 Uiso 1 1 calc R . . C29 C 0.6851(8) 0.0709(6) 0.8865(7) 0.135(4) Uani 1 1 d . . . H29A H 0.7545 0.0915 0.8612 0.203 Uiso 1 1 calc R . . H29B H 0.6336 0.0438 0.8495 0.203 Uiso 1 1 calc R . . H29C H 0.7048 0.0259 0.9247 0.203 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 0.0754(11) 0.0856(11) 0.0998(14) 0.0105(10) 0.0287(10) 0.0077(10) O1 0.413(18) 0.249(10) 0.078(4) 0.047(5) 0.085(7) 0.206(12) O2 0.154(7) 0.167(8) 0.48(2) 0.087(11) -0.066(11) -0.061(7) O3 0.108(4) 0.203(7) 0.125(5) 0.047(5) 0.041(4) 0.084(5) F1 0.290(12) 0.147(5) 0.194(7) 0.029(5) -0.059(8) -0.060(7) F2 0.185(7) 0.212(7) 0.153(5) 0.018(5) 0.009(5) 0.120(6) F3 0.212(7) 0.183(5) 0.073(3) 0.009(3) 0.012(4) 0.074(5) C30 0.136(7) 0.111(6) 0.061(5) -0.020(4) -0.009(5) 0.025(6) N1 0.049(2) 0.063(2) 0.052(3) 0.005(2) 0.004(2) 0.000(2) N2 0.049(2) 0.064(3) 0.049(3) 0.008(2) 0.001(2) 0.002(2) C1 0.049(3) 0.058(3) 0.047(3) 0.007(2) 0.003(2) 0.000(2) C2 0.053(3) 0.062(3) 0.055(3) -0.002(3) 0.001(3) 0.007(3) C3 0.061(4) 0.085(4) 0.054(3) 0.002(3) 0.002(3) 0.006(3) C4 0.059(3) 0.075(4) 0.065(4) 0.019(3) -0.004(3) 0.000(3) C5 0.072(4) 0.056(3) 0.076(4) 0.008(3) 0.008(3) -0.005(3) C6 0.062(3) 0.061(3) 0.063(4) 0.004(3) 0.000(3) -0.004(3) C7 0.096(5) 0.068(4) 0.071(4) -0.005(3) -0.001(4) 0.004(3) C8 0.091(5) 0.106(5) 0.068(4) 0.033(4) 0.003(4) 0.004(4) C9 0.111(6) 0.078(4) 0.070(4) -0.006(3) -0.004(4) -0.016(4) C10 0.040(3) 0.065(3) 0.044(3) 0.004(2) 0.006(2) -0.001(2) C11 0.054(3) 0.062(3) 0.056(3) 0.001(3) 0.003(3) -0.005(3) C12 0.076(4) 0.083(4) 0.059(4) -0.008(3) -0.003(3) -0.016(3) C13 0.065(4) 0.082(4) 0.077(4) 0.008(4) -0.014(3) 0.003(3) C14 0.058(3) 0.068(4) 0.077(4) 0.006(3) -0.011(3) -0.002(3) C15 0.046(3) 0.060(3) 0.059(3) 0.007(3) -0.004(2) 0.002(2) C16 0.091(5) 0.066(4) 0.071(4) 0.001(3) 0.007(3) -0.008(3) C17 0.114(7) 0.117(6) 0.128(7) 0.029(6) -0.068(6) -0.002(5) C18 0.084(4) 0.064(3) 0.079(4) -0.010(3) -0.010(4) -0.002(3) C19 0.044(3) 0.072(3) 0.062(4) 0.020(3) 0.008(3) 0.010(3) C20 0.064(4) 0.069(4) 0.095(5) 0.015(4) 0.006(3) 0.010(3) C21 0.085(5) 0.078(5) 0.151(9) 0.051(6) 0.036(6) 0.004(4) C22 0.078(5) 0.138(8) 0.091(6) 0.058(6) 0.025(5) 0.020(5) C23 0.073(5) 0.166(8) 0.065(5) 0.003(5) 0.007(4) 0.001(5) C24 0.062(4) 0.101(5) 0.081(5) 0.018(4) 0.012(3) -0.008(4) C25 0.057(3) 0.072(3) 0.055(3) 0.014(3) 0.010(3) 0.001(3) C26 0.045(3) 0.106(5) 0.076(4) 0.025(4) 0.013(3) 0.010(3) C27 0.056(3) 0.053(3) 0.051(3) 0.004(2) 0.005(3) 0.003(2) C28 0.054(4) 0.245(13) 0.131(7) 0.090(9) -0.012(5) -0.023(6) C29 0.115(7) 0.108(6) 0.183(10) 0.057(6) 0.088(7) 0.049(5) _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 1.330(11) . ? S1 O3 1.385(6) . ? S1 O1 1.394(8) . ? S1 C30 1.760(9) . ? F1 C30 1.288(11) . ? F2 C30 1.352(11) . ? F3 C30 1.230(8) . ? N1 C27 1.306(7) . ? N1 C1 1.456(7) . ? N1 C25 1.505(7) . ? N2 C27 1.323(6) . ? N2 C10 1.437(6) . ? N2 C26 1.497(8) . ? C1 C6 1.392(8) . ? C1 C2 1.393(7) . ? C2 C3 1.370(8) . ? C2 C7 1.523(8) . ? C3 C4 1.386(9) . ? C3 H3A 0.9300 . ? C4 C5 1.379(9) . ? C4 C8 1.503(8) . ? C5 C6 1.378(8) . ? C5 H5A 0.9300 . ? C6 C9 1.504(8) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.398(7) . ? C10 C15 1.399(7) . ? C11 C12 1.382(8) . ? C11 C16 1.518(9) . ? C12 C13 1.364(9) . ? C12 H12A 0.9300 . ? C13 C14 1.384(9) . ? C13 C17 1.515(10) . ? C14 C15 1.382(8) . ? C14 H14A 0.9300 . ? C15 C18 1.493(8) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.370(9) . ? C19 C20 1.401(9) . ? C19 C26 1.499(8) . ? C20 C21 1.376(11) . ? C20 H20A 0.9300 . ? C21 C22 1.325(13) . ? C21 H21A 0.9300 . ? C22 C23 1.356(12) . ? C22 H22A 0.9300 . ? C23 C24 1.388(10) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 C29 1.471(10) . ? C25 C28 1.496(11) . ? C25 C26 1.520(8) . ? C26 H26A 0.9800 . ? C27 H27A 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 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 107.9(7) . . ? O2 S1 O1 121.2(9) . . ? O3 S1 O1 114.8(7) . . ? O2 S1 C30 102.4(7) . . ? O3 S1 C30 105.5(5) . . ? O1 S1 C30 103.0(5) . . ? F3 C30 F1 107.8(10) . . ? F3 C30 F2 109.5(8) . . ? F1 C30 F2 95.5(8) . . ? F3 C30 S1 118.0(7) . . ? F1 C30 S1 112.6(6) . . ? F2 C30 S1 111.1(7) . . ? C27 N1 C1 125.7(4) . . ? C27 N1 C25 110.8(4) . . ? C1 N1 C25 123.1(4) . . ? C27 N2 C10 126.2(4) . . ? C27 N2 C26 108.8(5) . . ? C10 N2 C26 124.9(4) . . ? C6 C1 C2 122.0(5) . . ? C6 C1 N1 119.4(5) . . ? C2 C1 N1 118.6(4) . . ? C3 C2 C1 117.1(5) . . ? C3 C2 C7 119.6(5) . . ? C1 C2 C7 123.2(5) . . ? C2 C3 C4 123.6(6) . . ? C2 C3 H3A 118.2 . . ? C4 C3 H3A 118.2 . . ? C5 C4 C3 116.5(5) . . ? C5 C4 C8 122.2(6) . . ? C3 C4 C8 121.3(6) . . ? C6 C5 C4 123.3(5) . . ? C6 C5 H5A 118.3 . . ? C4 C5 H5A 118.3 . . ? C5 C6 C1 117.2(5) . . ? C5 C6 C9 119.5(5) . . ? C1 C6 C9 123.1(5) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 122.0(5) . . ? C11 C10 N2 118.5(5) . . ? C15 C10 N2 119.4(5) . . ? C12 C11 C10 117.3(5) . . ? C12 C11 C16 119.5(5) . . ? C10 C11 C16 123.2(5) . . ? C13 C12 C11 122.6(6) . . ? C13 C12 H12A 118.7 . . ? C11 C12 H12A 118.7 . . ? C12 C13 C14 118.7(6) . . ? C12 C13 C17 120.3(7) . . ? C14 C13 C17 121.0(6) . . ? C15 C14 C13 122.1(6) . . ? C15 C14 H14A 118.9 . . ? C13 C14 H14A 118.9 . . ? C14 C15 C10 117.2(5) . . ? C14 C15 C18 120.4(5) . . ? C10 C15 C18 122.4(5) . . ? 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 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 119.2(6) . . ? C24 C19 C26 124.7(6) . . ? C20 C19 C26 116.1(6) . . ? C21 C20 C19 118.5(8) . . ? C21 C20 H20A 120.8 . . ? C19 C20 H20A 120.8 . . ? C22 C21 C20 122.4(8) . . ? C22 C21 H21A 118.8 . . ? C20 C21 H21A 118.8 . . ? C21 C22 C23 119.8(8) . . ? C21 C22 H22A 120.1 . . ? C23 C22 H22A 120.1 . . ? C22 C23 C24 120.8(8) . . ? C22 C23 H23A 119.6 . . ? C24 C23 H23A 119.6 . . ? C19 C24 C23 119.3(7) . . ? C19 C24 H24A 120.3 . . ? C23 C24 H24A 120.3 . . ? C29 C25 C28 101.4(7) . . ? C29 C25 N1 110.8(5) . . ? C28 C25 N1 115.0(5) . . ? C29 C25 C26 114.0(6) . . ? C28 C25 C26 115.8(6) . . ? N1 C25 C26 100.4(4) . . ? N2 C26 C19 115.9(5) . . ? N2 C26 C25 103.0(5) . . ? C19 C26 C25 119.7(5) . . ? N2 C26 H26A 105.7 . . ? C19 C26 H26A 105.7 . . ? C25 C26 H26A 105.7 . . ? N1 C27 N2 112.6(5) . . ? N1 C27 H27A 123.7 . . ? N2 C27 H27A 123.7 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 C30 F3 63.0(12) . . . . ? O3 S1 C30 F3 -49.7(10) . . . . ? O1 S1 C30 F3 -170.4(10) . . . . ? O2 S1 C30 F1 -170.4(10) . . . . ? O3 S1 C30 F1 76.9(9) . . . . ? O1 S1 C30 F1 -43.8(11) . . . . ? O2 S1 C30 F2 -64.6(10) . . . . ? O3 S1 C30 F2 -177.3(7) . . . . ? O1 S1 C30 F2 62.0(10) . . . . ? C27 N1 C1 C6 81.0(7) . . . . ? C25 N1 C1 C6 -91.7(6) . . . . ? C27 N1 C1 C2 -99.5(6) . . . . ? C25 N1 C1 C2 87.8(6) . . . . ? C6 C1 C2 C3 2.7(8) . . . . ? N1 C1 C2 C3 -176.7(5) . . . . ? C6 C1 C2 C7 -177.1(6) . . . . ? N1 C1 C2 C7 3.4(8) . . . . ? C1 C2 C3 C4 0.5(9) . . . . ? C7 C2 C3 C4 -179.6(6) . . . . ? C2 C3 C4 C5 -2.8(9) . . . . ? C2 C3 C4 C8 179.0(6) . . . . ? C3 C4 C5 C6 1.9(10) . . . . ? C8 C4 C5 C6 -179.9(6) . . . . ? C4 C5 C6 C1 1.1(9) . . . . ? C4 C5 C6 C9 -175.3(6) . . . . ? C2 C1 C6 C5 -3.5(9) . . . . ? N1 C1 C6 C5 175.9(5) . . . . ? C2 C1 C6 C9 172.8(6) . . . . ? N1 C1 C6 C9 -7.7(9) . . . . ? C27 N2 C10 C11 -64.5(7) . . . . ? C26 N2 C10 C11 119.2(6) . . . . ? C27 N2 C10 C15 117.9(6) . . . . ? C26 N2 C10 C15 -58.3(7) . . . . ? C15 C10 C11 C12 2.4(8) . . . . ? N2 C10 C11 C12 -175.1(5) . . . . ? C15 C10 C11 C16 -179.5(5) . . . . ? N2 C10 C11 C16 3.1(8) . . . . ? C10 C11 C12 C13 -1.4(9) . . . . ? C16 C11 C12 C13 -179.6(7) . . . . ? C11 C12 C13 C14 -0.5(11) . . . . ? C11 C12 C13 C17 178.3(7) . . . . ? C12 C13 C14 C15 1.5(10) . . . . ? C17 C13 C14 C15 -177.3(7) . . . . ? C13 C14 C15 C10 -0.5(9) . . . . ? C13 C14 C15 C18 -179.9(7) . . . . ? C11 C10 C15 C14 -1.5(8) . . . . ? N2 C10 C15 C14 176.0(5) . . . . ? C11 C10 C15 C18 177.9(5) . . . . ? N2 C10 C15 C18 -4.7(8) . . . . ? C24 C19 C20 C21 -2.2(9) . . . . ? C26 C19 C20 C21 -179.5(6) . . . . ? C19 C20 C21 C22 0.2(11) . . . . ? C20 C21 C22 C23 1.0(13) . . . . ? C21 C22 C23 C24 -0.3(13) . . . . ? C20 C19 C24 C23 2.8(10) . . . . ? C26 C19 C24 C23 179.9(7) . . . . ? C22 C23 C24 C19 -1.6(12) . . . . ? C27 N1 C25 C29 -103.4(7) . . . . ? C1 N1 C25 C29 70.3(8) . . . . ? C27 N1 C25 C28 142.4(7) . . . . ? C1 N1 C25 C28 -43.9(8) . . . . ? C27 N1 C25 C26 17.4(6) . . . . ? C1 N1 C25 C26 -168.9(5) . . . . ? C27 N2 C26 C19 150.5(5) . . . . ? C10 N2 C26 C19 -32.7(9) . . . . ? C27 N2 C26 C25 17.9(6) . . . . ? C10 N2 C26 C25 -165.4(5) . . . . ? C24 C19 C26 N2 -36.7(9) . . . . ? C20 C19 C26 N2 140.5(6) . . . . ? C24 C19 C26 C25 87.8(8) . . . . ? C20 C19 C26 C25 -95.1(7) . . . . ? C29 C25 C26 N2 98.7(7) . . . . ? C28 C25 C26 N2 -144.3(6) . . . . ? N1 C25 C26 N2 -19.8(6) . . . . ? C29 C25 C26 C19 -31.8(9) . . . . ? C28 C25 C26 C19 85.3(8) . . . . ? N1 C25 C26 C19 -150.2(6) . . . . ? C1 N1 C27 N2 179.6(4) . . . . ? C25 N1 C27 N2 -6.9(6) . . . . ? C10 N2 C27 N1 175.9(5) . . . . ? C26 N2 C27 N1 -7.3(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.494 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.060 data_cd212276 _database_code_depnum_ccdc_archive 'CCDC 887380' #TrackingRef 'web_deposit_cif_file_2_JunZhang_1340017342.cd212276.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H33 F3 N2 O3 S' _chemical_formula_weight 546.63 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.6967(11) _cell_length_b 18.3660(12) _cell_length_c 18.5592(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5691.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3743 _cell_measurement_theta_min 4.436 _cell_measurement_theta_max 41.371 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.312 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.145 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.60957 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 31583 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5307 _reflns_number_gt 3454 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0720P)^2^+1.3090P] 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 5307 _refine_ls_number_parameters 420 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.0860 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.016 _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 N1 N 0.05284(10) 0.00996(9) 0.28150(8) 0.0447(4) Uani 1 1 d . . . N2 N 0.09209(11) -0.07558(9) 0.35563(9) 0.0525(5) Uani 1 1 d . . . C1 C 0.10563(12) -0.04022(11) 0.29556(10) 0.0457(5) Uani 1 1 d . . . H1 H 0.1490 -0.0501 0.2657 0.055 Uiso 1 1 calc R . . C2 C 0.01632(16) -0.05132(13) 0.38746(13) 0.0654(7) Uani 1 1 d . . . H2A H 0.0238 -0.0366 0.4372 0.078 Uiso 1 1 calc R . . H2B H -0.0236 -0.0897 0.3856 0.078 Uiso 1 1 calc R . . C3 C -0.00876(13) 0.01368(11) 0.34058(11) 0.0486(5) Uani 1 1 d . . . H3 H -0.0617 0.0038 0.3200 0.058 Uiso 1 1 calc R . . C4 C -0.01080(12) 0.08637(12) 0.37787(10) 0.0453(5) Uani 1 1 d . . . C5 C 0.04568(15) 0.10654(15) 0.42864(12) 0.0631(6) Uani 1 1 d . . . H5 H 0.0884 0.0758 0.4391 0.076 Uiso 1 1 calc R . . C6 C 0.0383(2) 0.17290(18) 0.46384(13) 0.0811(9) Uani 1 1 d . . . H6 H 0.0760 0.1866 0.4982 0.097 Uiso 1 1 calc R . . C7 C -0.0244(2) 0.21830(16) 0.44807(16) 0.0845(9) Uani 1 1 d . . . H7 H -0.0294 0.2623 0.4724 0.101 Uiso 1 1 calc R . . C8 C -0.07919(18) 0.19963(15) 0.39731(17) 0.0811(8) Uani 1 1 d . . . H8 H -0.1210 0.2311 0.3860 0.097 Uiso 1 1 calc R . . C9 C -0.07240(14) 0.13374(13) 0.36269(13) 0.0597(6) Uani 1 1 d . . . H9 H -0.1103 0.1209 0.3282 0.072 Uiso 1 1 calc R . . C10 C 0.14021(14) -0.13178(14) 0.38777(13) 0.0598(6) Uani 1 1 d . . . C11 C 0.19127(18) -0.11171(19) 0.44269(16) 0.0894(9) Uani 1 1 d . . . H11 H 0.1954 -0.0631 0.4562 0.107 Uiso 1 1 calc R . . C12 C 0.2357(2) -0.1633(3) 0.4771(2) 0.1221(14) Uani 1 1 d . . . H12 H 0.2716 -0.1500 0.5130 0.146 Uiso 1 1 calc R . . C13 C 0.2270(3) -0.2340(3) 0.4585(3) 0.1241(17) Uani 1 1 d . . . H13 H 0.2564 -0.2693 0.4828 0.149 Uiso 1 1 calc R . . C14 C 0.1761(3) -0.25445(19) 0.4047(2) 0.1057(13) Uani 1 1 d . . . H14 H 0.1713 -0.3035 0.3931 0.127 Uiso 1 1 calc R . . C15 C 0.13060(18) -0.20310(15) 0.36644(15) 0.0744(8) Uani 1 1 d . . . C16 C 0.0758(2) -0.22349(17) 0.3070(2) 0.1075(11) Uani 1 1 d . . . H16A H 0.0235 -0.2041 0.3164 0.161 Uiso 1 1 calc R . . H16B H 0.0728 -0.2756 0.3036 0.161 Uiso 1 1 calc R . . H16C H 0.0957 -0.2040 0.2625 0.161 Uiso 1 1 calc R . . C17 C 0.04754(12) 0.05087(11) 0.21500(10) 0.0458(5) Uani 1 1 d . . . C18 C -0.00533(15) 0.02538(13) 0.16217(12) 0.0577(6) Uani 1 1 d . . . C19 C -0.00826(19) 0.06507(16) 0.09832(13) 0.0785(8) Uani 1 1 d . . . H19 H -0.0427 0.0503 0.0618 0.094 Uiso 1 1 calc R . . C20 C 0.0385(2) 0.12543(16) 0.08829(14) 0.0855(9) Uani 1 1 d . . . H20 H 0.0358 0.1505 0.0448 0.103 Uiso 1 1 calc R . . C21 C 0.08892(18) 0.14933(13) 0.14074(13) 0.0692(7) Uani 1 1 d . . . H21 H 0.1199 0.1906 0.1327 0.083 Uiso 1 1 calc R . . C22 C 0.09468(13) 0.11291(11) 0.20614(11) 0.0492(5) Uani 1 1 d . . . C23 C 0.15252(13) 0.14126(13) 0.26227(12) 0.0575(6) Uani 1 1 d . . . H23 H 0.1479 0.1103 0.3050 0.069 Uiso 1 1 calc R . . C24 C 0.23822(16) 0.13556(19) 0.23467(18) 0.0949(10) Uani 1 1 d . . . H24A H 0.2489 0.0863 0.2201 0.142 Uiso 1 1 calc R . . H24B H 0.2747 0.1492 0.2723 0.142 Uiso 1 1 calc R . . H24C H 0.2451 0.1675 0.1942 0.142 Uiso 1 1 calc R . . C25 C 0.13222(18) 0.21911(14) 0.28459(15) 0.0769(8) Uani 1 1 d . . . H25A H 0.1396 0.2511 0.2442 0.115 Uiso 1 1 calc R . . H25B H 0.1668 0.2339 0.3232 0.115 Uiso 1 1 calc R . . H25C H 0.0775 0.2213 0.3003 0.115 Uiso 1 1 calc R . . C26 C -0.05525(16) -0.04314(15) 0.17094(14) 0.0730(7) Uani 1 1 d . . . H26 H -0.0513 -0.0581 0.2215 0.088 Uiso 1 1 calc R . . C27 C -0.0209(3) -0.10398(19) 0.1258(2) 0.1317(16) Uani 1 1 d . . . H27A H -0.0230 -0.0906 0.0758 0.198 Uiso 1 1 calc R . . H27B H -0.0517 -0.1475 0.1333 0.198 Uiso 1 1 calc R . . H27C H 0.0337 -0.1125 0.1396 0.198 Uiso 1 1 calc R . . C28 C -0.1430(2) -0.0297(3) 0.1549(3) 0.1543(18) Uani 1 1 d . . . H28A H -0.1621 0.0099 0.1840 0.231 Uiso 1 1 calc R . . H28B H -0.1732 -0.0728 0.1657 0.231 Uiso 1 1 calc R . . H28C H -0.1493 -0.0177 0.1049 0.231 Uiso 1 1 calc R . . S1 S 0.2284(2) 0.1200(2) 0.6439(2) 0.0660(6) Uani 0.70 1 d PDU A 1 O1 O 0.1739(7) 0.1627(7) 0.6176(7) 0.179(7) Uani 0.50 1 d PD A 1 O2 O 0.2007(10) 0.0694(5) 0.6947(5) 0.207(4) Uani 0.50 1 d PDU A 1 O3 O 0.2994(7) 0.1420(7) 0.6719(8) 0.207(6) Uani 0.50 1 d PDU A 1 F1 F 0.1827(5) 0.0237(5) 0.5550(6) 0.168(3) Uani 0.40 1 d PDU A 1 F2 F 0.2780(10) -0.0043(6) 0.5931(10) 0.204(8) Uani 0.40 1 d PDU A 1 F3 F 0.2851(13) 0.0816(8) 0.5204(10) 0.273(13) Uani 0.40 1 d PDU A 1 C29 C 0.2501(5) 0.0575(5) 0.5756(5) 0.078(3) Uani 0.50 1 d PD A 1 S1' S 0.2264(6) 0.1060(5) 0.6279(5) 0.103(3) Uani 0.30 1 d PDU B 2 O1' O 0.2126(7) 0.1851(6) 0.6096(5) 0.134(4) Uani 0.50 1 d PDU B 2 O2' O 0.1628(5) 0.0692(9) 0.6422(7) 0.302(10) Uani 0.50 1 d PDU B 2 O3' O 0.2809(5) 0.1133(6) 0.6906(4) 0.135(4) Uani 0.50 1 d PDU B 2 F1' F 0.2329(4) 0.0716(3) 0.5060(3) 0.134(2) Uani 0.60 1 d PDU B 2 F2' F 0.3165(5) 0.0177(4) 0.5738(6) 0.152(3) Uani 0.60 1 d PDU B 2 F3' F 0.3414(3) 0.1172(3) 0.5409(2) 0.1448(16) Uani 0.60 1 d PDU B 2 C29' C 0.2832(6) 0.0760(6) 0.5588(6) 0.089(3) Uani 0.50 1 d PD B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0493(10) 0.0457(9) 0.0390(9) 0.0054(7) 0.0075(7) 0.0043(8) N2 0.0543(11) 0.0539(11) 0.0492(10) 0.0147(8) 0.0095(8) 0.0059(9) C1 0.0451(12) 0.0491(12) 0.0428(11) 0.0034(9) 0.0062(9) 0.0004(10) C2 0.0742(17) 0.0579(14) 0.0641(15) 0.0142(12) 0.0265(13) 0.0111(12) C3 0.0476(12) 0.0530(13) 0.0451(11) 0.0056(9) 0.0100(9) 0.0024(10) C4 0.0447(12) 0.0549(12) 0.0362(10) 0.0043(9) 0.0075(9) 0.0002(10) C5 0.0630(15) 0.0826(17) 0.0438(13) 0.0047(12) -0.0026(11) -0.0025(13) C6 0.097(2) 0.099(2) 0.0469(14) -0.0084(15) 0.0015(14) -0.0355(19) C7 0.114(3) 0.0656(18) 0.0736(19) -0.0175(15) 0.0261(19) -0.0147(18) C8 0.080(2) 0.0629(17) 0.100(2) -0.0052(16) 0.0182(17) 0.0134(15) C9 0.0514(14) 0.0604(14) 0.0674(15) -0.0036(12) 0.0007(11) 0.0073(11) C10 0.0574(14) 0.0656(16) 0.0565(14) 0.0221(12) 0.0108(11) 0.0096(12) C11 0.0774(19) 0.109(2) 0.082(2) 0.0283(17) -0.0157(16) -0.0049(18) C12 0.088(3) 0.174(4) 0.104(3) 0.054(3) -0.019(2) 0.010(3) C13 0.101(3) 0.161(4) 0.111(3) 0.080(3) 0.029(2) 0.061(3) C14 0.124(3) 0.088(2) 0.105(3) 0.042(2) 0.050(2) 0.047(2) C15 0.087(2) 0.0659(17) 0.0702(17) 0.0147(14) 0.0255(15) 0.0160(15) C16 0.145(3) 0.076(2) 0.102(2) -0.0117(18) 0.002(2) -0.005(2) C17 0.0528(13) 0.0486(12) 0.0360(11) 0.0025(9) 0.0055(9) 0.0075(10) C18 0.0682(15) 0.0586(14) 0.0464(12) -0.0054(10) -0.0031(11) 0.0020(12) C19 0.107(2) 0.0795(19) 0.0493(14) -0.0021(13) -0.0222(14) 0.0045(17) C20 0.137(3) 0.0711(18) 0.0484(15) 0.0173(13) -0.0082(16) 0.0087(19) C21 0.100(2) 0.0548(14) 0.0529(14) 0.0103(11) 0.0118(14) -0.0030(14) C22 0.0557(13) 0.0485(12) 0.0435(12) 0.0016(9) 0.0106(10) 0.0044(10) C23 0.0544(14) 0.0619(14) 0.0561(14) 0.0013(11) 0.0061(11) -0.0079(11) C24 0.0559(17) 0.117(3) 0.112(2) -0.017(2) 0.0130(16) -0.0050(17) C25 0.0843(19) 0.0678(16) 0.0786(18) -0.0126(14) 0.0036(14) -0.0098(14) C26 0.0820(19) 0.0800(18) 0.0568(15) -0.0135(13) -0.0027(13) -0.0182(15) C27 0.187(4) 0.081(2) 0.128(3) -0.038(2) 0.052(3) -0.041(3) C28 0.082(3) 0.170(4) 0.210(5) 0.017(4) -0.022(3) -0.034(3) S1 0.0561(10) 0.0771(9) 0.0649(11) 0.0057(8) -0.0016(8) -0.0150(8) O1 0.158(9) 0.220(14) 0.160(11) -0.092(9) -0.098(8) 0.142(9) O2 0.295(13) 0.177(7) 0.150(7) 0.008(6) 0.089(8) -0.060(9) O3 0.105(5) 0.197(10) 0.318(15) -0.140(10) -0.051(8) -0.031(6) F1 0.155(6) 0.164(6) 0.186(8) -0.081(6) -0.049(6) -0.016(5) F2 0.34(2) 0.064(5) 0.205(11) 0.012(5) -0.065(14) 0.029(8) F3 0.34(2) 0.131(8) 0.35(2) -0.076(13) 0.30(2) -0.077(12) C29 0.066(6) 0.085(6) 0.082(5) 0.013(4) -0.003(5) 0.023(5) S1' 0.077(4) 0.139(7) 0.093(5) 0.052(5) 0.010(3) 0.037(4) O1' 0.232(12) 0.097(4) 0.073(4) 0.017(4) 0.019(6) 0.080(6) O2' 0.123(6) 0.51(2) 0.273(14) 0.227(16) -0.039(7) -0.201(11) O3' 0.128(7) 0.213(10) 0.063(3) 0.012(4) -0.051(4) 0.078(7) F1' 0.156(5) 0.135(4) 0.110(4) -0.033(3) -0.066(4) 0.010(4) F2' 0.145(5) 0.085(5) 0.226(8) -0.011(5) -0.020(4) 0.059(4) F3' 0.111(3) 0.201(5) 0.123(3) 0.012(3) 0.039(2) -0.001(3) C29' 0.075(7) 0.087(7) 0.106(8) -0.025(7) 0.023(7) -0.015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.302(3) . ? N1 C17 1.448(2) . ? N1 C3 1.505(2) . ? N2 C1 1.310(2) . ? N2 C10 1.438(3) . ? N2 C2 1.466(3) . ? C1 H1 0.9300 . ? C2 C3 1.536(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.504(3) . ? C3 H3 0.9800 . ? C4 C9 1.376(3) . ? C4 C5 1.384(3) . ? C5 C6 1.388(4) . ? C5 H5 0.9300 . ? C6 C7 1.370(4) . ? C6 H6 0.9300 . ? C7 C8 1.357(4) . ? C7 H7 0.9300 . ? C8 C9 1.375(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.378(4) . ? C10 C11 1.379(4) . ? C11 C12 1.362(5) . ? C11 H11 0.9300 . ? C12 C13 1.351(6) . ? C12 H12 0.9300 . ? C13 C14 1.365(6) . ? C13 H13 0.9300 . ? C14 C15 1.403(4) . ? C14 H14 0.9300 . ? C15 C16 1.481(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C22 1.395(3) . ? C17 C18 1.400(3) . ? C18 C19 1.392(3) . ? C18 C26 1.518(3) . ? C19 C20 1.369(4) . ? C19 H19 0.9300 . ? C20 C21 1.360(4) . ? C20 H20 0.9300 . ? C21 C22 1.389(3) . ? C21 H21 0.9300 . ? C22 C23 1.513(3) . ? C23 C24 1.523(4) . ? C23 C25 1.527(3) . ? C23 H23 0.9800 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.510(4) . ? C26 C28 1.515(5) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? S1 O1 1.297(9) . ? S1 O3 1.356(10) . ? S1 O2 1.401(9) . ? S1 C29 1.747(10) . ? F1 C29 1.340(11) . ? F2 C29 1.269(12) . ? F3 C29 1.260(13) . ? S1' O2' 1.286(11) . ? S1' O3' 1.483(11) . ? S1' O1' 1.510(12) . ? S1' C29' 1.687(13) . ? F1' C29' 1.294(11) . ? F2' C29' 1.238(12) . ? F3' C29' 1.275(11) . ? 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 C1 N1 C17 125.43(16) . . ? C1 N1 C3 110.43(15) . . ? C17 N1 C3 123.76(16) . . ? C1 N2 C10 127.78(18) . . ? C1 N2 C2 109.96(18) . . ? C10 N2 C2 122.24(17) . . ? N1 C1 N2 113.87(18) . . ? N1 C1 H1 123.1 . . ? N2 C1 H1 123.1 . . ? N2 C2 C3 104.09(17) . . ? N2 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? N2 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 109.0 . . ? C4 C3 N1 113.02(16) . . ? C4 C3 C2 115.82(18) . . ? N1 C3 C2 101.02(16) . . ? C4 C3 H3 108.9 . . ? N1 C3 H3 108.9 . . ? C2 C3 H3 108.9 . . ? C9 C4 C5 118.7(2) . . ? C9 C4 C3 118.94(19) . . ? C5 C4 C3 122.4(2) . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 119.4(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C4 121.5(2) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? C15 C10 C11 122.6(3) . . ? C15 C10 N2 119.9(2) . . ? C11 C10 N2 117.4(2) . . ? C12 C11 C10 119.8(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 119.4(4) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.2(4) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 121.5(4) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C10 C15 C14 115.5(3) . . ? C10 C15 C16 121.8(3) . . ? C14 C15 C16 122.7(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 123.13(19) . . ? C22 C17 N1 119.34(18) . . ? C18 C17 N1 117.53(19) . . ? C19 C18 C17 116.3(2) . . ? C19 C18 C26 120.4(2) . . ? C17 C18 C26 123.2(2) . . ? C20 C19 C18 121.3(2) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 121.1(2) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 120.9(2) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C21 C22 C17 117.2(2) . . ? C21 C22 C23 118.7(2) . . ? C17 C22 C23 124.08(18) . . ? C22 C23 C24 110.1(2) . . ? C22 C23 C25 111.6(2) . . ? C24 C23 C25 111.4(2) . . ? C22 C23 H23 107.9 . . ? C24 C23 H23 107.9 . . ? C25 C23 H23 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C28 112.2(3) . . ? C27 C26 C18 110.2(2) . . ? C28 C26 C18 112.0(3) . . ? C27 C26 H26 107.4 . . ? C28 C26 H26 107.4 . . ? C18 C26 H26 107.4 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O1 S1 O3 125.3(9) . . ? O1 S1 O2 115.0(9) . . ? O3 S1 O2 103.2(8) . . ? O1 S1 C29 105.7(7) . . ? O3 S1 C29 107.0(7) . . ? O2 S1 C29 97.0(5) . . ? F3 C29 F2 110.6(15) . . ? F3 C29 F1 108.6(12) . . ? F2 C29 F1 88.1(11) . . ? F3 C29 S1 117.1(10) . . ? F2 C29 S1 118.5(10) . . ? F1 C29 S1 109.7(7) . . ? O2' S1' O3' 113.1(9) . . ? O2' S1' O1' 115.2(10) . . ? O3' S1' O1' 100.5(8) . . ? O2' S1' C29' 116.7(11) . . ? O3' S1' C29' 106.3(8) . . ? O1' S1' C29' 103.2(8) . . ? F2' C29' F3' 103.3(9) . . ? F2' C29' F1' 114.1(10) . . ? F3' C29' F1' 109.5(9) . . ? F2' C29' S1' 111.3(9) . . ? F3' C29' S1' 115.7(8) . . ? F1' C29' S1' 103.4(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 N1 C1 N2 -171.96(18) . . . . ? C3 N1 C1 N2 1.2(2) . . . . ? C10 N2 C1 N1 -177.4(2) . . . . ? C2 N2 C1 N1 4.3(3) . . . . ? C1 N2 C2 C3 -7.5(3) . . . . ? C10 N2 C2 C3 174.0(2) . . . . ? C1 N1 C3 C4 118.76(19) . . . . ? C17 N1 C3 C4 -68.0(2) . . . . ? C1 N1 C3 C2 -5.6(2) . . . . ? C17 N1 C3 C2 167.65(19) . . . . ? N2 C2 C3 C4 -115.0(2) . . . . ? N2 C2 C3 N1 7.5(2) . . . . ? N1 C3 C4 C9 104.5(2) . . . . ? C2 C3 C4 C9 -139.7(2) . . . . ? N1 C3 C4 C5 -77.6(2) . . . . ? C2 C3 C4 C5 38.3(3) . . . . ? C9 C4 C5 C6 1.2(3) . . . . ? C3 C4 C5 C6 -176.8(2) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C8 -1.0(4) . . . . ? C6 C7 C8 C9 1.4(4) . . . . ? C7 C8 C9 C4 -0.6(4) . . . . ? C5 C4 C9 C8 -0.8(3) . . . . ? C3 C4 C9 C8 177.3(2) . . . . ? C1 N2 C10 C15 -85.1(3) . . . . ? C2 N2 C10 C15 93.0(3) . . . . ? C1 N2 C10 C11 98.8(3) . . . . ? C2 N2 C10 C11 -83.0(3) . . . . ? C15 C10 C11 C12 1.3(4) . . . . ? N2 C10 C11 C12 177.2(3) . . . . ? C10 C11 C12 C13 -2.2(5) . . . . ? C11 C12 C13 C14 1.6(6) . . . . ? C12 C13 C14 C15 0.1(6) . . . . ? C11 C10 C15 C14 0.3(4) . . . . ? N2 C10 C15 C14 -175.5(2) . . . . ? C11 C10 C15 C16 -179.6(3) . . . . ? N2 C10 C15 C16 4.6(4) . . . . ? C13 C14 C15 C10 -1.0(4) . . . . ? C13 C14 C15 C16 178.9(3) . . . . ? C1 N1 C17 C22 -84.8(3) . . . . ? C3 N1 C17 C22 102.9(2) . . . . ? C1 N1 C17 C18 95.0(2) . . . . ? C3 N1 C17 C18 -77.3(3) . . . . ? C22 C17 C18 C19 0.8(3) . . . . ? N1 C17 C18 C19 -179.0(2) . . . . ? C22 C17 C18 C26 178.5(2) . . . . ? N1 C17 C18 C26 -1.3(3) . . . . ? C17 C18 C19 C20 0.3(4) . . . . ? C26 C18 C19 C20 -177.5(3) . . . . ? C18 C19 C20 C21 -0.8(5) . . . . ? C19 C20 C21 C22 0.3(4) . . . . ? C20 C21 C22 C17 0.7(4) . . . . ? C20 C21 C22 C23 179.2(2) . . . . ? C18 C17 C22 C21 -1.3(3) . . . . ? N1 C17 C22 C21 178.48(19) . . . . ? C18 C17 C22 C23 -179.7(2) . . . . ? N1 C17 C22 C23 0.1(3) . . . . ? C21 C22 C23 C24 -64.0(3) . . . . ? C17 C22 C23 C24 114.4(3) . . . . ? C21 C22 C23 C25 60.2(3) . . . . ? C17 C22 C23 C25 -121.5(2) . . . . ? C19 C18 C26 C27 72.3(4) . . . . ? C17 C18 C26 C27 -105.3(3) . . . . ? C19 C18 C26 C28 -53.5(4) . . . . ? C17 C18 C26 C28 129.0(3) . . . . ? O1 S1 C29 F3 68.4(18) . . . . ? O3 S1 C29 F3 -67.1(17) . . . . ? O2 S1 C29 F3 -173.2(17) . . . . ? O1 S1 C29 F2 -154.9(13) . . . . ? O3 S1 C29 F2 69.6(13) . . . . ? O2 S1 C29 F2 -36.5(14) . . . . ? O1 S1 C29 F1 -56.0(11) . . . . ? O3 S1 C29 F1 168.5(10) . . . . ? O2 S1 C29 F1 62.4(10) . . . . ? O2' S1' C29' F2' -69.4(13) . . . . ? O3' S1' C29' F2' 57.9(11) . . . . ? O1' S1' C29' F2' 163.2(9) . . . . ? O2' S1' C29' F3' 173.2(10) . . . . ? O3' S1' C29' F3' -59.5(11) . . . . ? O1' S1' C29' F3' 45.7(11) . . . . ? O2' S1' C29' F1' 53.5(12) . . . . ? O3' S1' C29' F1' -179.2(8) . . . . ? O1' S1' C29' F1' -73.9(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.033 data_mo_dm12279_0m _database_code_depnum_ccdc_archive 'CCDC 887381' #TrackingRef 'web_deposit_cif_file_3_JunZhang_1340017342.mo_dm12279_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H28 N2 S2' _chemical_formula_weight 444.63 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' 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.0291(10) _cell_length_b 15.1285(15) _cell_length_c 15.5536(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2359.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9974 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 29.19 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9352 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21311 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 29.24 _reflns_number_total 6400 _reflns_number_gt 5931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0517P)^2^+0.2200P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 6400 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.71774(4) 0.60901(2) 0.23853(2) 0.03133(8) Uani 1 1 d . . . S2 S 0.67652(5) 0.41136(3) 0.22051(2) 0.04014(10) Uani 1 1 d . . . N1 N 0.74231(10) 0.47564(7) 0.42592(6) 0.0218(2) Uani 1 1 d . . . N2 N 0.53349(10) 0.51259(7) 0.39977(6) 0.0211(2) Uani 1 1 d . . . C1 C 0.68398(12) 0.50765(8) 0.27302(7) 0.0227(2) Uani 1 1 d . . . C2 C 0.65356(12) 0.49932(8) 0.36657(7) 0.0203(2) Uani 1 1 d . . . C3 C 0.68121(13) 0.47698(9) 0.51207(8) 0.0248(2) Uani 1 1 d . . . H3A H 0.7170 0.5263 0.5470 0.030 Uiso 1 1 calc R . . H3B H 0.6972 0.4206 0.5427 0.030 Uiso 1 1 calc R . . C4 C 0.53156(12) 0.49013(8) 0.49346(7) 0.0211(2) Uani 1 1 d . . . H4 H 0.4850 0.4322 0.5010 0.025 Uiso 1 1 calc R . . C5 C 0.45769(13) 0.55967(9) 0.54471(8) 0.0229(2) Uani 1 1 d . . . C6 C 0.52209(15) 0.62977(10) 0.58488(10) 0.0321(3) Uani 1 1 d . . . H6 H 0.6166 0.6334 0.5839 0.039 Uiso 1 1 calc R . . C7 C 0.4477(2) 0.69458(11) 0.62658(10) 0.0411(4) Uani 1 1 d . . . H7 H 0.4922 0.7417 0.6549 0.049 Uiso 1 1 calc R . . C8 C 0.31107(19) 0.69121(11) 0.62726(10) 0.0428(4) Uani 1 1 d . . . H8 H 0.2613 0.7367 0.6545 0.051 Uiso 1 1 calc R . . C9 C 0.24624(16) 0.62149(12) 0.58823(10) 0.0405(4) Uani 1 1 d . . . H9 H 0.1516 0.6186 0.5892 0.049 Uiso 1 1 calc R . . C10 C 0.31918(14) 0.55532(10) 0.54741(9) 0.0300(3) Uani 1 1 d . . . H10 H 0.2742 0.5070 0.5213 0.036 Uiso 1 1 calc R . . C11 C 0.93899(16) 0.57150(10) 0.44128(11) 0.0369(3) Uani 1 1 d . . . H11A H 0.8891 0.6179 0.4113 0.055 Uiso 1 1 calc R . . H11B H 1.0340 0.5767 0.4273 0.055 Uiso 1 1 calc R . . H11C H 0.9266 0.5781 0.5035 0.055 Uiso 1 1 calc R . . C12 C 0.88803(12) 0.48092(9) 0.41292(8) 0.0250(3) Uani 1 1 d . . . H12 H 0.9050 0.4756 0.3498 0.030 Uiso 1 1 calc R . . C13 C 0.96030(12) 0.40495(9) 0.45672(8) 0.0251(2) Uani 1 1 d . . . C14 C 1.00501(15) 0.33419(10) 0.40739(9) 0.0322(3) Uani 1 1 d . . . H14 H 0.9847 0.3322 0.3478 0.039 Uiso 1 1 calc R . . C15 C 1.07920(18) 0.26615(11) 0.44433(11) 0.0402(3) Uani 1 1 d . . . H15 H 1.1101 0.2185 0.4098 0.048 Uiso 1 1 calc R . . C16 C 1.10766(16) 0.26811(11) 0.53113(11) 0.0391(4) Uani 1 1 d . . . H16 H 1.1591 0.2222 0.5563 0.047 Uiso 1 1 calc R . . C17 C 1.06114(17) 0.33712(12) 0.58147(10) 0.0394(4) Uani 1 1 d . . . H17 H 1.0786 0.3376 0.6415 0.047 Uiso 1 1 calc R . . C18 C 0.98899(15) 0.40561(11) 0.54432(9) 0.0339(3) Uani 1 1 d . . . H18 H 0.9590 0.4533 0.5790 0.041 Uiso 1 1 calc R . . C19 C 0.41594(12) 0.53712(9) 0.35230(7) 0.0215(2) Uani 1 1 d . . . C20 C 0.38695(12) 0.62695(9) 0.34087(8) 0.0238(2) Uani 1 1 d . . . C21 C 0.27257(14) 0.64828(9) 0.29373(8) 0.0275(3) Uani 1 1 d . . . H21 H 0.2515 0.7087 0.2843 0.033 Uiso 1 1 calc R . . C22 C 0.18946(13) 0.58396(10) 0.26055(8) 0.0303(3) Uani 1 1 d . . . C23 C 0.21818(13) 0.49568(10) 0.27647(9) 0.0306(3) Uani 1 1 d . . . H23 H 0.1590 0.4515 0.2557 0.037 Uiso 1 1 calc R . . C24 C 0.33126(13) 0.47009(9) 0.32207(8) 0.0255(2) Uani 1 1 d . . . C25 C 0.36044(16) 0.37379(10) 0.33839(11) 0.0352(3) Uani 1 1 d . . . H25A H 0.3430 0.3600 0.3989 0.053 Uiso 1 1 calc R . . H25B H 0.4541 0.3615 0.3251 0.053 Uiso 1 1 calc R . . H25C H 0.3031 0.3373 0.3018 0.053 Uiso 1 1 calc R . . C26 C 0.07165(17) 0.60955(14) 0.20578(11) 0.0457(4) Uani 1 1 d . . . H26A H 0.0205 0.6559 0.2349 0.069 Uiso 1 1 calc R . . H26B H 0.0146 0.5578 0.1967 0.069 Uiso 1 1 calc R . . H26C H 0.1032 0.6316 0.1501 0.069 Uiso 1 1 calc R . . C27 C 0.47077(15) 0.70060(9) 0.37710(10) 0.0324(3) Uani 1 1 d . . . H27A H 0.4251 0.7269 0.4266 0.049 Uiso 1 1 calc R . . H27B H 0.4845 0.7459 0.3329 0.049 Uiso 1 1 calc R . . H27C H 0.5572 0.6770 0.3954 0.049 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 0.03881(18) 0.03162(17) 0.02356(14) 0.00517(12) 0.00001(13) -0.00653(14) S2 0.0618(3) 0.03120(18) 0.02743(16) -0.00660(14) 0.01123(16) 0.00181(17) N1 0.0197(5) 0.0275(5) 0.0183(4) 0.0028(4) 0.0003(4) 0.0029(4) N2 0.0203(5) 0.0253(5) 0.0175(4) 0.0018(4) -0.0001(4) 0.0012(4) C1 0.0212(5) 0.0287(6) 0.0182(5) 0.0008(5) -0.0005(4) 0.0010(5) C2 0.0223(5) 0.0186(5) 0.0200(5) 0.0003(4) -0.0007(4) 0.0004(4) C3 0.0234(6) 0.0332(6) 0.0179(5) 0.0027(4) 0.0003(4) 0.0038(5) C4 0.0221(5) 0.0230(6) 0.0183(5) 0.0026(4) 0.0012(4) 0.0017(4) C5 0.0258(6) 0.0248(6) 0.0180(5) -0.0001(4) 0.0007(4) 0.0037(5) C6 0.0341(7) 0.0285(7) 0.0338(7) -0.0051(5) -0.0059(6) 0.0026(6) C7 0.0572(10) 0.0299(7) 0.0362(8) -0.0105(6) -0.0105(7) 0.0095(7) C8 0.0555(10) 0.0429(8) 0.0299(7) -0.0059(6) -0.0005(7) 0.0244(8) C9 0.0310(7) 0.0554(10) 0.0350(7) -0.0033(7) 0.0033(6) 0.0147(7) C10 0.0262(6) 0.0367(7) 0.0272(6) -0.0023(5) 0.0013(5) 0.0040(5) C11 0.0301(7) 0.0315(7) 0.0492(9) 0.0087(7) -0.0042(6) -0.0054(6) C12 0.0191(5) 0.0314(6) 0.0246(6) 0.0053(5) 0.0006(4) 0.0019(5) C13 0.0184(5) 0.0308(7) 0.0261(5) 0.0052(5) -0.0003(4) 0.0003(5) C14 0.0357(7) 0.0311(7) 0.0298(6) -0.0002(5) -0.0048(6) 0.0025(6) C15 0.0443(9) 0.0313(7) 0.0450(8) -0.0013(7) -0.0035(7) 0.0075(7) C16 0.0339(8) 0.0373(8) 0.0462(9) 0.0124(7) -0.0078(7) 0.0062(6) C17 0.0379(8) 0.0501(9) 0.0301(7) 0.0099(7) -0.0068(6) 0.0071(7) C18 0.0330(7) 0.0427(8) 0.0261(6) 0.0009(6) -0.0022(5) 0.0090(6) C19 0.0190(5) 0.0276(6) 0.0180(5) 0.0006(4) -0.0009(4) 0.0008(5) C20 0.0225(5) 0.0280(6) 0.0208(5) 0.0017(5) 0.0016(4) 0.0025(5) C21 0.0274(6) 0.0317(7) 0.0233(5) 0.0023(5) -0.0004(5) 0.0094(5) C22 0.0224(6) 0.0443(7) 0.0243(5) -0.0038(5) -0.0020(5) 0.0097(5) C23 0.0236(6) 0.0387(7) 0.0295(6) -0.0056(6) -0.0042(5) 0.0001(5) C24 0.0241(6) 0.0290(6) 0.0233(5) -0.0021(5) -0.0004(5) 0.0000(5) C25 0.0368(8) 0.0280(7) 0.0410(8) -0.0008(6) -0.0087(6) -0.0043(6) C26 0.0381(8) 0.0592(11) 0.0398(8) -0.0148(8) -0.0158(7) 0.0193(8) C27 0.0333(7) 0.0246(6) 0.0392(7) 0.0033(6) -0.0042(6) -0.0008(5) _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 C1 1.6595(13) . ? S2 C1 1.6717(13) . ? N1 C2 1.3313(15) . ? N1 C3 1.4735(15) . ? N1 C12 1.4776(16) . ? N2 C2 1.3255(16) . ? N2 C19 1.4397(16) . ? N2 C4 1.4964(15) . ? C1 C2 1.4920(16) . ? C3 C4 1.5415(17) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5136(17) . ? C4 H4 1.0000 . ? C5 C6 1.3901(19) . ? C5 C10 1.3914(19) . ? C6 C7 1.392(2) . ? C6 H6 0.9500 . ? C7 C8 1.372(3) . ? C7 H7 0.9500 . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 C10 1.393(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.528(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.5199(18) . ? C12 H12 1.0000 . ? C13 C14 1.391(2) . ? C13 C18 1.3926(18) . ? C14 C15 1.394(2) . ? C14 H14 0.9500 . ? C15 C16 1.380(2) . ? C15 H15 0.9500 . ? C16 C17 1.386(2) . ? C16 H16 0.9500 . ? C17 C18 1.390(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.4010(18) . ? C19 C24 1.4038(18) . ? C20 C21 1.3991(18) . ? C20 C27 1.5053(19) . ? C21 C22 1.381(2) . ? C21 H21 0.9500 . ? C22 C23 1.389(2) . ? C22 C26 1.5071(19) . ? C23 C24 1.3926(18) . ? C23 H23 0.9500 . ? C24 C25 1.5075(19) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C3 110.41(10) . . ? C2 N1 C12 123.49(11) . . ? C3 N1 C12 122.34(10) . . ? C2 N2 C19 125.68(10) . . ? C2 N2 C4 110.89(10) . . ? C19 N2 C4 123.18(10) . . ? C2 C1 S1 115.78(9) . . ? C2 C1 S2 113.19(9) . . ? S1 C1 S2 131.02(7) . . ? N2 C2 N1 112.21(10) . . ? N2 C2 C1 123.56(11) . . ? N1 C2 C1 124.20(11) . . ? N1 C3 C4 103.64(9) . . ? N1 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? N1 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? N2 C4 C5 111.18(10) . . ? N2 C4 C3 101.51(9) . . ? C5 C4 C3 117.86(11) . . ? N2 C4 H4 108.6 . . ? C5 C4 H4 108.6 . . ? C3 C4 H4 108.6 . . ? C6 C5 C10 119.10(13) . . ? C6 C5 C4 122.66(12) . . ? C10 C5 C4 118.15(12) . . ? C5 C6 C7 119.86(15) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.85(15) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.73(14) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 120.16(15) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 120.27(14) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C13 111.68(11) . . ? N1 C12 C11 109.87(12) . . ? C13 C12 C11 112.92(11) . . ? N1 C12 H12 107.4 . . ? C13 C12 H12 107.4 . . ? C11 C12 H12 107.4 . . ? C14 C13 C18 118.58(13) . . ? C14 C13 C12 119.24(12) . . ? C18 C13 C12 122.12(13) . . ? C13 C14 C15 120.86(14) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.85(15) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.94(14) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 120.14(14) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.61(15) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C20 C19 C24 122.18(12) . . ? C20 C19 N2 119.02(11) . . ? C24 C19 N2 118.75(11) . . ? C21 C20 C19 117.42(12) . . ? C21 C20 C27 118.90(12) . . ? C19 C20 C27 123.68(12) . . ? C22 C21 C20 121.87(13) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C23 119.06(12) . . ? C21 C22 C26 120.21(14) . . ? C23 C22 C26 120.70(14) . . ? C22 C23 C24 121.82(13) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C23 C24 C19 117.54(12) . . ? C23 C24 C25 120.83(12) . . ? C19 C24 C25 121.63(12) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C20 C27 H27A 109.5 . . ? C20 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C20 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N2 C2 N1 -178.80(11) . . . . ? C4 N2 C2 N1 -4.34(15) . . . . ? C19 N2 C2 C1 -0.40(19) . . . . ? C4 N2 C2 C1 174.05(11) . . . . ? C3 N1 C2 N2 -3.65(15) . . . . ? C12 N1 C2 N2 -162.19(12) . . . . ? C3 N1 C2 C1 177.97(11) . . . . ? C12 N1 C2 C1 19.42(19) . . . . ? S1 C1 C2 N2 84.71(14) . . . . ? S2 C1 C2 N2 -94.79(13) . . . . ? S1 C1 C2 N1 -97.08(13) . . . . ? S2 C1 C2 N1 83.41(14) . . . . ? C2 N1 C3 C4 9.55(14) . . . . ? C12 N1 C3 C4 168.39(12) . . . . ? C2 N2 C4 C5 135.96(11) . . . . ? C19 N2 C4 C5 -49.42(15) . . . . ? C2 N2 C4 C3 9.77(13) . . . . ? C19 N2 C4 C3 -175.61(11) . . . . ? N1 C3 C4 N2 -10.97(12) . . . . ? N1 C3 C4 C5 -132.62(11) . . . . ? N2 C4 C5 C6 -94.64(14) . . . . ? C3 C4 C5 C6 21.91(18) . . . . ? N2 C4 C5 C10 81.80(14) . . . . ? C3 C4 C5 C10 -161.66(12) . . . . ? C10 C5 C6 C7 -0.4(2) . . . . ? C4 C5 C6 C7 176.01(13) . . . . ? C5 C6 C7 C8 -1.2(2) . . . . ? C6 C7 C8 C9 1.8(3) . . . . ? C7 C8 C9 C10 -0.8(2) . . . . ? C6 C5 C10 C9 1.4(2) . . . . ? C4 C5 C10 C9 -175.14(12) . . . . ? C8 C9 C10 C5 -0.9(2) . . . . ? C2 N1 C12 C13 -144.27(12) . . . . ? C3 N1 C12 C13 59.66(16) . . . . ? C2 N1 C12 C11 89.63(15) . . . . ? C3 N1 C12 C11 -66.44(15) . . . . ? N1 C12 C13 C14 102.26(14) . . . . ? C11 C12 C13 C14 -133.32(14) . . . . ? N1 C12 C13 C18 -80.83(16) . . . . ? C11 C12 C13 C18 43.59(18) . . . . ? C18 C13 C14 C15 -1.2(2) . . . . ? C12 C13 C14 C15 175.79(14) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C17 0.7(3) . . . . ? C15 C16 C17 C18 -1.8(3) . . . . ? C16 C17 C18 C13 1.3(3) . . . . ? C14 C13 C18 C17 0.2(2) . . . . ? C12 C13 C18 C17 -176.72(14) . . . . ? C2 N2 C19 C20 -90.25(15) . . . . ? C4 N2 C19 C20 95.94(14) . . . . ? C2 N2 C19 C24 92.35(16) . . . . ? C4 N2 C19 C24 -81.46(15) . . . . ? C24 C19 C20 C21 -3.27(19) . . . . ? N2 C19 C20 C21 179.42(11) . . . . ? C24 C19 C20 C27 176.05(13) . . . . ? N2 C19 C20 C27 -1.26(19) . . . . ? C19 C20 C21 C22 1.00(19) . . . . ? C27 C20 C21 C22 -178.35(13) . . . . ? C20 C21 C22 C23 1.8(2) . . . . ? C20 C21 C22 C26 -176.44(13) . . . . ? C21 C22 C23 C24 -2.6(2) . . . . ? C26 C22 C23 C24 175.70(13) . . . . ? C22 C23 C24 C19 0.4(2) . . . . ? C22 C23 C24 C25 -179.87(14) . . . . ? C20 C19 C24 C23 2.59(19) . . . . ? N2 C19 C24 C23 179.90(11) . . . . ? C20 C19 C24 C25 -177.13(13) . . . . ? N2 C19 C24 C25 0.18(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.24 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.248 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.039 data_a20104a _database_code_depnum_ccdc_archive 'CCDC 887382' #TrackingRef 'web_deposit_cif_file_4_JunZhang_1340017342.a20104a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H35 F3 N2 O3 S' _chemical_formula_weight 608.70 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 10.433(4) _cell_length_b 17.320(7) _cell_length_c 19.236(8) _cell_angle_alpha 66.656(5) _cell_angle_beta 84.785(5) _cell_angle_gamma 88.956(5) _cell_volume 3178(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 993 _cell_measurement_theta_min 2.316 _cell_measurement_theta_max 27.450 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9333 _exptl_absorpt_correction_T_max 0.9681 _exptl_absorpt_process_details sadabs _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_% 4.88 _diffrn_reflns_number 13216 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.01 _reflns_number_total 10966 _reflns_number_gt 7450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.1443P)^2^+0.3625P] 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 10966 _refine_ls_number_parameters 795 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.2275 _refine_ls_wR_factor_gt 0.2017 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.003 _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 0.72708(9) 0.24821(5) 0.18713(5) 0.0678(3) Uani 1 1 d . . . S2 S 0.25780(9) 0.74743(6) 0.18826(5) 0.0722(3) Uani 1 1 d . . . O1 O 0.7872(3) 0.32828(19) 0.15810(19) 0.1075(10) Uani 1 1 d . . . O2 O 0.6474(3) 0.2285(3) 0.25556(17) 0.1124(11) Uani 1 1 d . . . O3 O 0.8063(5) 0.1832(2) 0.1859(2) 0.1513(17) Uani 1 1 d . . . O4 O 0.1988(3) 0.82685(19) 0.16220(17) 0.1000(9) Uani 1 1 d . . . O5 O 0.1860(5) 0.6832(2) 0.1789(2) 0.1496(17) Uani 1 1 d . . . O6 O 0.3105(3) 0.72296(19) 0.25987(15) 0.0939(9) Uani 1 1 d . . . N1 N 0.9320(2) 0.87692(13) 0.27069(12) 0.0431(5) Uani 1 1 d . . . N2 N 1.0205(2) 0.98899(14) 0.17722(13) 0.0488(6) Uani 1 1 d . . . N3 N 1.0127(2) 0.37978(13) 0.26736(12) 0.0473(5) Uani 1 1 d . . . N4 N 0.9227(2) 0.48817(14) 0.18206(13) 0.0516(6) Uani 1 1 d . . . F1 F 0.6757(5) 0.2738(3) 0.05217(18) 0.1898(19) Uani 1 1 d U . . F2 F 0.5447(5) 0.1932(3) 0.1351(2) 0.206(2) Uani 1 1 d U . . F3 F 0.5340(5) 0.3193(4) 0.1134(3) 0.212(2) Uani 1 1 d . . . F4 F 0.4750(4) 0.8246(3) 0.1273(2) 0.1686(16) Uani 1 1 d . . . F5 F 0.4703(5) 0.7019(3) 0.1362(3) 0.207(2) Uani 1 1 d . . . F6 F 0.3717(4) 0.7912(3) 0.05268(18) 0.1786(18) Uani 1 1 d . . . C1 C 0.9750(3) 0.91286(17) 0.19881(16) 0.0469(6) Uani 1 1 d D . . H1 H 0.966(3) 0.8859(16) 0.1674(13) 0.047(7) Uiso 1 1 d D . . C2 C 0.9596(3) 0.93527(16) 0.30999(15) 0.0468(6) Uani 1 1 d . . . C3 C 0.9914(3) 1.01851(17) 0.23903(16) 0.0537(7) Uani 1 1 d . . . H3A H 0.9184 1.0556 0.2294 0.064 Uiso 1 1 calc R . . H3B H 1.0651 1.0477 0.2454 0.064 Uiso 1 1 calc R . . C4 C 0.8434(3) 0.80457(16) 0.29820(15) 0.0451(6) Uani 1 1 d . . . C5 C 0.8872(3) 0.72413(17) 0.33909(15) 0.0476(6) Uani 1 1 d . . . C6 C 0.8007(3) 0.65684(18) 0.35699(17) 0.0559(7) Uani 1 1 d . . . H6 H 0.8285 0.6025 0.3834 0.067 Uiso 1 1 calc R . . C7 C 0.6760(3) 0.66769(19) 0.33717(18) 0.0584(8) Uani 1 1 d . . . C8 C 0.6355(3) 0.7488(2) 0.29950(17) 0.0581(8) Uani 1 1 d . . . H8 H 0.5507 0.7571 0.2874 0.070 Uiso 1 1 calc R . . C9 C 0.7161(3) 0.81816(18) 0.27910(16) 0.0501(7) Uani 1 1 d . . . C10 C 1.0174(3) 0.70632(19) 0.36722(19) 0.0600(8) Uani 1 1 d . . . H10A H 1.0819 0.7290 0.3251 0.090 Uiso 1 1 calc R . . H10B H 1.0274 0.6466 0.3920 0.090 Uiso 1 1 calc R . . H10C H 1.0268 0.7318 0.4026 0.090 Uiso 1 1 calc R . . C11 C 0.5869(4) 0.5936(2) 0.3561(3) 0.0857(11) Uani 1 1 d . . . H11A H 0.6365 0.5440 0.3644 0.129 Uiso 1 1 calc R . . H11B H 0.5351 0.6035 0.3148 0.129 Uiso 1 1 calc R . . H11C H 0.5321 0.5859 0.4014 0.129 Uiso 1 1 calc R . . C12 C 0.6632(3) 0.9038(2) 0.2370(2) 0.0716(9) Uani 1 1 d . . . H12A H 0.6574 0.9124 0.1849 0.107 Uiso 1 1 calc R . . H12B H 0.7193 0.9460 0.2390 0.107 Uiso 1 1 calc R . . H12C H 0.5791 0.9077 0.2600 0.107 Uiso 1 1 calc R . . C13 C 0.8447(3) 0.93753(18) 0.36332(16) 0.0508(7) Uani 1 1 d . . . C14 C 0.7727(3) 1.0092(2) 0.35113(19) 0.0629(8) Uani 1 1 d . . . H14 H 0.7937 1.0581 0.3084 0.075 Uiso 1 1 calc R . . C15 C 0.6700(4) 1.0083(3) 0.4020(2) 0.0804(11) Uani 1 1 d . . . H15 H 0.6223 1.0566 0.3933 0.097 Uiso 1 1 calc R . . C16 C 0.6378(4) 0.9365(3) 0.4655(2) 0.0841(11) Uani 1 1 d . . . H16 H 0.5680 0.9361 0.4994 0.101 Uiso 1 1 calc R . . C17 C 0.7094(4) 0.8650(2) 0.4788(2) 0.0746(10) Uani 1 1 d . . . H17 H 0.6884 0.8164 0.5219 0.090 Uiso 1 1 calc R . . C18 C 0.8117(3) 0.8661(2) 0.42828(18) 0.0616(8) Uani 1 1 d . . . H18 H 0.8598 0.8178 0.4378 0.074 Uiso 1 1 calc R . . C19 C 1.0826(3) 0.90895(17) 0.35181(16) 0.0519(7) Uani 1 1 d . . . C20 C 1.1863(3) 0.87705(19) 0.32187(19) 0.0603(8) Uani 1 1 d . . . H20 H 1.1791 0.8674 0.2781 0.072 Uiso 1 1 calc R . . C21 C 1.3001(4) 0.8594(2) 0.3563(2) 0.0782(11) Uani 1 1 d . . . H21 H 1.3685 0.8375 0.3359 0.094 Uiso 1 1 calc R . . C22 C 1.3126(5) 0.8740(3) 0.4204(3) 0.0902(13) Uani 1 1 d . . . H22 H 1.3888 0.8614 0.4439 0.108 Uiso 1 1 calc R . . C23 C 1.2126(5) 0.9072(3) 0.4495(2) 0.0886(13) Uani 1 1 d . . . H23 H 1.2218 0.9184 0.4922 0.106 Uiso 1 1 calc R . . C24 C 1.0971(4) 0.9244(2) 0.41617(18) 0.0669(9) Uani 1 1 d . . . H24 H 1.0293 0.9463 0.4370 0.080 Uiso 1 1 calc R . . C25 C 1.0631(3) 1.04648(17) 0.10019(16) 0.0520(7) Uani 1 1 d . . . C26 C 1.1942(3) 1.06826(19) 0.08173(18) 0.0614(8) Uani 1 1 d . . . C27 C 1.2292(4) 1.1292(2) 0.00973(19) 0.0682(9) Uani 1 1 d . . . H27 H 1.3157 1.1443 -0.0045 0.082 Uiso 1 1 calc R . . C28 C 1.1397(4) 1.16830(19) -0.04172(17) 0.0639(9) Uani 1 1 d . . . C29 C 1.0136(4) 1.1433(2) -0.02132(18) 0.0668(9) Uani 1 1 d . . . H29 H 0.9533 1.1682 -0.0560 0.080 Uiso 1 1 calc R . . C30 C 0.9723(3) 1.08223(19) 0.04916(17) 0.0598(8) Uani 1 1 d . . . C31 C 1.2930(4) 1.0293(3) 0.1359(2) 0.0847(11) Uani 1 1 d . . . H31A H 1.2707 1.0375 0.1820 0.127 Uiso 1 1 calc R . . H31B H 1.3755 1.0551 0.1135 0.127 Uiso 1 1 calc R . . H31C H 1.2964 0.9702 0.1471 0.127 Uiso 1 1 calc R . . C32 C 1.1818(5) 1.2374(2) -0.11765(19) 0.0891(13) Uani 1 1 d . . . H32A H 1.2176 1.2837 -0.1098 0.134 Uiso 1 1 calc R . . H32B H 1.1089 1.2560 -0.1468 0.134 Uiso 1 1 calc R . . H32C H 1.2456 1.2165 -0.1446 0.134 Uiso 1 1 calc R . . C33 C 0.8311(4) 1.0578(3) 0.0677(2) 0.0812(11) Uani 1 1 d . . . H33A H 0.8204 0.9995 0.0769 0.122 Uiso 1 1 calc R . . H33B H 0.7842 1.0916 0.0257 0.122 Uiso 1 1 calc R . . H33C H 0.7990 1.0668 0.1122 0.122 Uiso 1 1 calc R . . C34 C 0.9771(3) 0.41546(18) 0.19834(17) 0.0509(7) Uani 1 1 d D . . H34 H 0.986(3) 0.3921(17) 0.1625(14) 0.054(8) Uiso 1 1 d D . . C35 C 0.9700(3) 0.43379(16) 0.31180(16) 0.0489(7) Uani 1 1 d . . . C36 C 0.9354(3) 0.51555(18) 0.24472(17) 0.0581(8) Uani 1 1 d . . . H36A H 0.8553 0.5381 0.2576 0.070 Uiso 1 1 calc R . . H36B H 1.0031 0.5580 0.2312 0.070 Uiso 1 1 calc R . . C37 C 1.1028(3) 0.31118(17) 0.28751(15) 0.0485(7) Uani 1 1 d . . . C38 C 1.0583(3) 0.22818(18) 0.32591(16) 0.0539(7) Uani 1 1 d . . . C39 C 1.1477(4) 0.16509(19) 0.33692(18) 0.0636(8) Uani 1 1 d . . . H39 H 1.1192 0.1095 0.3617 0.076 Uiso 1 1 calc R . . C40 C 1.2760(4) 0.1807(2) 0.31300(19) 0.0674(9) Uani 1 1 d . . . C41 C 1.3175(3) 0.2635(2) 0.27912(18) 0.0635(8) Uani 1 1 d . . . H41 H 1.4050 0.2752 0.2653 0.076 Uiso 1 1 calc R . . C42 C 1.2335(3) 0.33014(19) 0.26491(16) 0.0541(7) Uani 1 1 d . . . C43 C 0.9208(3) 0.2057(2) 0.3563(2) 0.0735(10) Uani 1 1 d . . . H43A H 0.9016 0.2204 0.3992 0.110 Uiso 1 1 calc R . . H43B H 0.9069 0.1463 0.3717 0.110 Uiso 1 1 calc R . . H43C H 0.8656 0.2359 0.3174 0.110 Uiso 1 1 calc R . . C44 C 1.3678(5) 0.1100(3) 0.3217(3) 0.0985(14) Uani 1 1 d . . . H44A H 1.3351 0.0598 0.3633 0.148 Uiso 1 1 calc R . . H44B H 1.4504 0.1248 0.3317 0.148 Uiso 1 1 calc R . . H44C H 1.3765 0.1002 0.2758 0.148 Uiso 1 1 calc R . . C45 C 1.2881(4) 0.4180(2) 0.2252(2) 0.0760(10) Uani 1 1 d . . . H45A H 1.3500 0.4275 0.2551 0.114 Uiso 1 1 calc R . . H45B H 1.2199 0.4575 0.2189 0.114 Uiso 1 1 calc R . . H45C H 1.3291 0.4251 0.1763 0.114 Uiso 1 1 calc R . . C46 C 0.8460(3) 0.39647(17) 0.36405(17) 0.0522(7) Uani 1 1 d . . . C47 C 0.7445(3) 0.3679(2) 0.33681(19) 0.0617(8) Uani 1 1 d . . . H47 H 0.7542 0.3682 0.2881 0.074 Uiso 1 1 calc R . . C48 C 0.6315(3) 0.3395(2) 0.3812(2) 0.0728(9) Uani 1 1 d . . . H48 H 0.5652 0.3206 0.3623 0.087 Uiso 1 1 calc R . . C49 C 0.6140(4) 0.3385(2) 0.4530(2) 0.0786(10) Uani 1 1 d . . . H49 H 0.5371 0.3183 0.4829 0.094 Uiso 1 1 calc R . . C50 C 0.7112(4) 0.3674(2) 0.4802(2) 0.0772(10) Uani 1 1 d . . . H50 H 0.7000 0.3671 0.5288 0.093 Uiso 1 1 calc R . . C51 C 0.8267(3) 0.3973(2) 0.43548(18) 0.0626(8) Uani 1 1 d . . . H51 H 0.8913 0.4180 0.4541 0.075 Uiso 1 1 calc R . . C52 C 1.0785(3) 0.44212(17) 0.35544(15) 0.0497(7) Uani 1 1 d . . . C53 C 1.1212(3) 0.37098(18) 0.41349(16) 0.0547(7) Uani 1 1 d . . . H53 H 1.0801 0.3194 0.4261 0.066 Uiso 1 1 calc R . . C54 C 1.2232(3) 0.3758(2) 0.45253(19) 0.0642(8) Uani 1 1 d . . . H54 H 1.2522 0.3273 0.4899 0.077 Uiso 1 1 calc R . . C55 C 1.2819(4) 0.4521(2) 0.4362(2) 0.0716(9) Uani 1 1 d . . . H55 H 1.3499 0.4556 0.4630 0.086 Uiso 1 1 calc R . . C56 C 1.2398(4) 0.5232(2) 0.3801(2) 0.0710(9) Uani 1 1 d . . . H56 H 1.2796 0.5749 0.3688 0.085 Uiso 1 1 calc R . . C57 C 1.1386(3) 0.51835(19) 0.34024(19) 0.0610(8) Uani 1 1 d . . . H57 H 1.1106 0.5670 0.3027 0.073 Uiso 1 1 calc R . . C58 C 0.8903(3) 0.54510(18) 0.10770(17) 0.0558(7) Uani 1 1 d . . . C59 C 0.7612(4) 0.5614(2) 0.0954(2) 0.0653(9) Uani 1 1 d . . . C60 C 0.7363(4) 0.6216(2) 0.0236(2) 0.0765(11) Uani 1 1 d . . . H60 H 0.6511 0.6334 0.0133 0.092 Uiso 1 1 calc R . . C61 C 0.8314(5) 0.6636(2) -0.0319(2) 0.0725(10) Uani 1 1 d . . . C62 C 0.9565(4) 0.6446(2) -0.01698(19) 0.0761(10) Uani 1 1 d . . . H62 H 1.0216 0.6725 -0.0546 0.091 Uiso 1 1 calc R . . C63 C 0.9905(4) 0.5853(2) 0.05207(18) 0.0667(9) Uani 1 1 d . . . C64 C 0.6536(4) 0.5177(3) 0.1542(2) 0.0858(11) Uani 1 1 d . . . H64A H 0.6533 0.4588 0.1641 0.129 Uiso 1 1 calc R . . H64B H 0.5732 0.5413 0.1360 0.129 Uiso 1 1 calc R . . H64C H 0.6654 0.5249 0.2002 0.129 Uiso 1 1 calc R . . C65 C 0.7998(6) 0.7304(3) -0.1069(2) 0.1026(15) Uani 1 1 d . . . H65A H 0.7355 0.7089 -0.1276 0.154 Uiso 1 1 calc R . . H65B H 0.8761 0.7457 -0.1417 0.154 Uiso 1 1 calc R . . H65C H 0.7677 0.7789 -0.0992 0.154 Uiso 1 1 calc R . . C66 C 1.1291(4) 0.5665(3) 0.0639(2) 0.0939(13) Uani 1 1 d . . . H66A H 1.1529 0.5829 0.1032 0.141 Uiso 1 1 calc R . . H66B H 1.1812 0.5973 0.0175 0.141 Uiso 1 1 calc R . . H66C H 1.1422 0.5073 0.0785 0.141 Uiso 1 1 calc R . . C67 C 0.6141(7) 0.2576(4) 0.1184(3) 0.1150(18) Uani 1 1 d . . . C68 C 0.4000(6) 0.7649(4) 0.1222(3) 0.1116(16) 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 0.0734(6) 0.0605(5) 0.0697(5) -0.0261(4) -0.0057(4) 0.0020(4) S2 0.0751(6) 0.0692(6) 0.0690(6) -0.0232(4) -0.0098(4) 0.0057(4) O1 0.128(3) 0.0829(19) 0.115(2) -0.0402(17) -0.018(2) -0.0302(18) O2 0.093(2) 0.165(3) 0.0837(19) -0.056(2) 0.0040(16) -0.011(2) O3 0.192(4) 0.102(3) 0.150(3) -0.044(2) -0.010(3) 0.071(3) O4 0.109(2) 0.096(2) 0.102(2) -0.0440(17) -0.0305(17) 0.0432(18) O5 0.182(4) 0.109(3) 0.145(3) -0.028(2) -0.045(3) -0.063(3) O6 0.0918(19) 0.110(2) 0.0684(16) -0.0220(15) -0.0155(14) 0.0113(17) N1 0.0456(12) 0.0356(11) 0.0471(12) -0.0152(10) -0.0054(10) 0.0026(9) N2 0.0577(14) 0.0390(12) 0.0475(13) -0.0153(10) -0.0032(11) 0.0015(10) N3 0.0570(14) 0.0366(12) 0.0476(13) -0.0157(10) -0.0046(11) -0.0012(10) N4 0.0642(15) 0.0406(13) 0.0489(13) -0.0159(10) -0.0089(11) 0.0015(11) F1 0.247(4) 0.242(4) 0.083(2) -0.065(2) -0.001(2) -0.115(4) F2 0.224(4) 0.244(4) 0.160(3) -0.083(3) -0.015(3) -0.141(4) F3 0.167(4) 0.260(6) 0.206(5) -0.072(4) -0.107(4) 0.044(4) F4 0.118(3) 0.228(4) 0.144(3) -0.060(3) 0.015(2) -0.050(3) F5 0.185(4) 0.222(5) 0.208(4) -0.091(4) 0.010(3) 0.115(4) F6 0.175(3) 0.284(5) 0.086(2) -0.085(3) -0.008(2) 0.043(3) C1 0.0502(16) 0.0403(15) 0.0503(16) -0.0174(13) -0.0080(13) 0.0043(12) C2 0.0615(17) 0.0340(13) 0.0459(14) -0.0163(11) -0.0078(13) 0.0029(12) C3 0.0705(19) 0.0395(15) 0.0513(16) -0.0184(13) -0.0048(14) 0.0003(13) C4 0.0512(16) 0.0379(14) 0.0466(14) -0.0178(12) -0.0012(12) -0.0018(12) C5 0.0516(16) 0.0411(15) 0.0493(15) -0.0181(12) -0.0007(12) 0.0035(12) C6 0.068(2) 0.0377(15) 0.0564(17) -0.0140(13) -0.0016(15) 0.0011(13) C7 0.0647(19) 0.0507(17) 0.0581(17) -0.0202(14) -0.0021(15) -0.0083(14) C8 0.0534(17) 0.0610(19) 0.0617(18) -0.0260(15) -0.0055(14) -0.0017(14) C9 0.0528(16) 0.0481(16) 0.0492(15) -0.0186(13) -0.0064(13) 0.0032(13) C10 0.0564(18) 0.0432(16) 0.073(2) -0.0148(14) -0.0076(15) 0.0050(13) C11 0.080(2) 0.068(2) 0.104(3) -0.027(2) -0.010(2) -0.0193(19) C12 0.0571(19) 0.057(2) 0.091(2) -0.0173(18) -0.0196(18) 0.0098(15) C13 0.0584(17) 0.0489(16) 0.0507(16) -0.0255(13) -0.0061(13) 0.0033(13) C14 0.071(2) 0.0588(19) 0.0659(19) -0.0319(16) -0.0109(16) 0.0140(16) C15 0.076(2) 0.093(3) 0.090(3) -0.055(2) -0.014(2) 0.028(2) C16 0.071(2) 0.111(3) 0.090(3) -0.064(3) 0.012(2) -0.001(2) C17 0.085(3) 0.073(2) 0.072(2) -0.0393(19) 0.0149(19) -0.0147(19) C18 0.073(2) 0.0530(18) 0.0622(19) -0.0287(15) 0.0070(16) -0.0048(15) C19 0.0631(18) 0.0373(14) 0.0503(16) -0.0112(12) -0.0076(14) -0.0087(13) C20 0.0549(18) 0.0532(18) 0.0687(19) -0.0185(15) -0.0108(15) -0.0001(14) C21 0.062(2) 0.060(2) 0.100(3) -0.016(2) -0.017(2) -0.0028(16) C22 0.081(3) 0.080(3) 0.091(3) -0.007(2) -0.037(2) -0.015(2) C23 0.106(3) 0.093(3) 0.060(2) -0.017(2) -0.025(2) -0.034(3) C24 0.081(2) 0.064(2) 0.0532(17) -0.0191(15) -0.0086(16) -0.0183(17) C25 0.0655(19) 0.0382(14) 0.0484(15) -0.0142(12) 0.0010(14) -0.0016(13) C26 0.071(2) 0.0481(17) 0.0621(19) -0.0194(15) 0.0012(16) -0.0053(15) C27 0.078(2) 0.0578(19) 0.064(2) -0.0225(16) 0.0121(18) -0.0142(17) C28 0.098(3) 0.0472(17) 0.0465(16) -0.0211(14) 0.0047(17) -0.0071(17) C29 0.094(3) 0.0562(19) 0.0489(17) -0.0186(15) -0.0105(17) 0.0061(18) C30 0.074(2) 0.0513(17) 0.0512(17) -0.0182(14) -0.0032(15) 0.0004(15) C31 0.066(2) 0.079(2) 0.091(3) -0.013(2) -0.010(2) -0.0074(19) C32 0.146(4) 0.063(2) 0.052(2) -0.0195(17) 0.011(2) -0.020(2) C33 0.072(2) 0.088(3) 0.070(2) -0.014(2) -0.0177(18) 0.006(2) C34 0.0573(17) 0.0439(16) 0.0523(17) -0.0198(13) -0.0041(14) -0.0037(13) C35 0.0621(17) 0.0359(14) 0.0490(15) -0.0173(12) -0.0048(13) 0.0008(12) C36 0.077(2) 0.0427(16) 0.0554(17) -0.0188(14) -0.0127(15) 0.0033(14) C37 0.0600(17) 0.0390(14) 0.0484(15) -0.0185(12) -0.0087(13) 0.0026(12) C38 0.0698(19) 0.0415(15) 0.0500(16) -0.0165(13) -0.0099(14) -0.0008(14) C39 0.085(2) 0.0413(16) 0.0590(18) -0.0127(14) -0.0117(17) 0.0063(16) C40 0.083(2) 0.056(2) 0.0586(19) -0.0168(16) -0.0157(17) 0.0186(17) C41 0.063(2) 0.069(2) 0.0579(18) -0.0242(16) -0.0066(15) 0.0101(16) C42 0.0587(18) 0.0519(17) 0.0494(16) -0.0181(13) -0.0026(13) -0.0001(14) C43 0.075(2) 0.0438(17) 0.092(2) -0.0165(17) -0.0063(19) -0.0102(16) C44 0.101(3) 0.076(3) 0.100(3) -0.017(2) -0.014(3) 0.036(2) C45 0.065(2) 0.059(2) 0.093(3) -0.0216(19) 0.0070(19) -0.0091(17) C46 0.0581(17) 0.0412(15) 0.0556(17) -0.0173(13) -0.0068(14) 0.0074(13) C47 0.065(2) 0.0555(18) 0.0629(19) -0.0220(15) -0.0054(16) 0.0011(15) C48 0.058(2) 0.067(2) 0.088(3) -0.0260(19) -0.0054(18) 0.0005(16) C49 0.063(2) 0.072(2) 0.089(3) -0.023(2) 0.009(2) 0.0029(18) C50 0.078(2) 0.082(3) 0.068(2) -0.0298(19) 0.0085(19) 0.010(2) C51 0.069(2) 0.0577(19) 0.0614(19) -0.0245(15) -0.0036(16) 0.0051(16) C52 0.0605(17) 0.0405(15) 0.0489(15) -0.0188(12) -0.0029(13) -0.0014(13) C53 0.0681(19) 0.0432(16) 0.0527(16) -0.0184(13) -0.0071(14) -0.0024(14) C54 0.072(2) 0.0561(18) 0.0630(19) -0.0194(15) -0.0170(16) 0.0061(16) C55 0.071(2) 0.068(2) 0.080(2) -0.0306(19) -0.0226(18) -0.0025(17) C56 0.077(2) 0.0505(18) 0.087(2) -0.0251(17) -0.0188(19) -0.0111(16) C57 0.074(2) 0.0426(16) 0.0654(19) -0.0183(14) -0.0141(16) -0.0005(14) C58 0.073(2) 0.0434(16) 0.0517(17) -0.0179(13) -0.0158(15) 0.0050(14) C59 0.078(2) 0.0500(18) 0.071(2) -0.0250(16) -0.0190(18) 0.0096(16) C60 0.096(3) 0.064(2) 0.079(2) -0.034(2) -0.041(2) 0.024(2) C61 0.112(3) 0.057(2) 0.055(2) -0.0257(16) -0.025(2) 0.014(2) C62 0.109(3) 0.066(2) 0.0507(18) -0.0206(16) -0.0072(19) -0.006(2) C63 0.082(2) 0.0597(19) 0.0544(18) -0.0169(15) -0.0131(17) -0.0003(17) C64 0.070(2) 0.079(3) 0.096(3) -0.020(2) -0.015(2) 0.009(2) C65 0.161(5) 0.084(3) 0.065(2) -0.026(2) -0.042(3) 0.032(3) C66 0.080(3) 0.103(3) 0.072(2) -0.006(2) 0.000(2) -0.014(2) C67 0.149(5) 0.112(4) 0.086(3) -0.040(3) -0.014(3) -0.034(4) C68 0.123(4) 0.135(5) 0.088(3) -0.056(3) -0.019(3) 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 O3 1.391(3) . ? S1 O1 1.408(3) . ? S1 O2 1.413(3) . ? S1 C67 1.808(6) . ? S2 O4 1.415(3) . ? S2 O5 1.430(4) . ? S2 O6 1.431(3) . ? S2 C68 1.810(6) . ? N1 C1 1.310(4) . ? N1 C4 1.461(3) . ? N1 C2 1.527(3) . ? N2 C1 1.300(4) . ? N2 C25 1.453(4) . ? N2 C3 1.476(4) . ? N3 C34 1.309(4) . ? N3 C37 1.451(4) . ? N3 C35 1.534(4) . ? N4 C34 1.304(4) . ? N4 C58 1.446(4) . ? N4 C36 1.476(4) . ? F1 C67 1.301(6) . ? F2 C67 1.255(6) . ? F3 C67 1.323(7) . ? F4 C68 1.347(7) . ? F5 C68 1.255(6) . ? F6 C68 1.291(6) . ? C2 C13 1.516(4) . ? C2 C19 1.542(4) . ? C2 C3 1.558(4) . ? C4 C5 1.394(4) . ? C4 C9 1.400(4) . ? C5 C6 1.398(4) . ? C5 C10 1.489(4) . ? C6 C7 1.378(5) . ? C7 C8 1.379(4) . ? C7 C11 1.502(5) . ? C8 C9 1.381(4) . ? C9 C12 1.503(4) . ? C13 C18 1.387(4) . ? C13 C14 1.389(4) . ? C14 C15 1.379(5) . ? C15 C16 1.374(6) . ? C16 C17 1.380(6) . ? C17 C18 1.372(5) . ? C19 C20 1.387(5) . ? C19 C24 1.387(4) . ? C20 C21 1.383(5) . ? C21 C22 1.370(6) . ? C22 C23 1.364(7) . ? C23 C24 1.388(6) . ? C25 C30 1.382(4) . ? C25 C26 1.401(5) . ? C26 C27 1.389(4) . ? C26 C31 1.488(5) . ? C27 C28 1.388(5) . ? C28 C29 1.365(5) . ? C28 C32 1.509(4) . ? C29 C30 1.384(4) . ? C30 C33 1.511(5) . ? C35 C52 1.511(4) . ? C35 C46 1.543(4) . ? C35 C36 1.555(4) . ? C37 C38 1.396(4) . ? C37 C42 1.397(4) . ? C38 C39 1.387(4) . ? C38 C43 1.496(5) . ? C39 C40 1.371(5) . ? C40 C41 1.378(5) . ? C40 C44 1.507(5) . ? C41 C42 1.390(4) . ? C42 C45 1.501(4) . ? C46 C51 1.376(4) . ? C46 C47 1.403(4) . ? C47 C48 1.366(5) . ? C48 C49 1.370(6) . ? C49 C50 1.369(6) . ? C50 C51 1.393(5) . ? C52 C57 1.383(4) . ? C52 C53 1.394(4) . ? C53 C54 1.379(4) . ? C54 C55 1.374(5) . ? C55 C56 1.374(5) . ? C56 C57 1.382(5) . ? C58 C59 1.393(5) . ? C58 C63 1.398(5) . ? C59 C60 1.406(5) . ? C59 C64 1.495(5) . ? C60 C61 1.368(6) . ? C61 C62 1.369(6) . ? C61 C65 1.509(5) . ? C62 C63 1.392(5) . ? C63 C66 1.494(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O1 115.0(3) . . ? O3 S1 O2 114.2(2) . . ? O1 S1 O2 114.9(2) . . ? O3 S1 C67 104.0(3) . . ? O1 S1 C67 103.2(2) . . ? O2 S1 C67 103.3(3) . . ? O4 S2 O5 113.9(2) . . ? O4 S2 O6 115.17(19) . . ? O5 S2 O6 115.3(2) . . ? O4 S2 C68 103.0(2) . . ? O5 S2 C68 104.6(3) . . ? O6 S2 C68 102.7(2) . . ? C1 N1 C4 121.2(2) . . ? C1 N1 C2 108.9(2) . . ? C4 N1 C2 127.9(2) . . ? C1 N2 C25 127.1(2) . . ? C1 N2 C3 109.3(2) . . ? C25 N2 C3 121.8(2) . . ? C34 N3 C37 121.3(2) . . ? C34 N3 C35 109.2(2) . . ? C37 N3 C35 128.1(2) . . ? C34 N4 C58 126.1(2) . . ? C34 N4 C36 108.8(2) . . ? C58 N4 C36 122.7(2) . . ? N2 C1 N1 115.1(3) . . ? C13 C2 N1 110.6(2) . . ? C13 C2 C19 111.6(2) . . ? N1 C2 C19 110.7(2) . . ? C13 C2 C3 115.8(2) . . ? N1 C2 C3 99.9(2) . . ? C19 C2 C3 107.6(2) . . ? N2 C3 C2 102.9(2) . . ? C5 C4 C9 121.6(3) . . ? C5 C4 N1 120.2(2) . . ? C9 C4 N1 118.1(2) . . ? C4 C5 C6 117.2(3) . . ? C4 C5 C10 124.1(3) . . ? C6 C5 C10 118.6(3) . . ? C7 C6 C5 122.7(3) . . ? C6 C7 C8 117.9(3) . . ? C6 C7 C11 121.0(3) . . ? C8 C7 C11 121.1(3) . . ? C7 C8 C9 122.6(3) . . ? C8 C9 C4 117.9(3) . . ? C8 C9 C12 118.4(3) . . ? C4 C9 C12 123.6(3) . . ? C18 C13 C14 118.2(3) . . ? C18 C13 C2 119.1(3) . . ? C14 C13 C2 122.7(3) . . ? C15 C14 C13 120.4(3) . . ? C16 C15 C14 120.5(4) . . ? C15 C16 C17 119.7(4) . . ? C18 C17 C16 119.7(4) . . ? C17 C18 C13 121.4(3) . . ? C20 C19 C24 118.3(3) . . ? C20 C19 C2 120.8(3) . . ? C24 C19 C2 120.6(3) . . ? C21 C20 C19 120.8(3) . . ? C22 C21 C20 120.4(4) . . ? C23 C22 C21 119.5(4) . . ? C22 C23 C24 120.9(4) . . ? C19 C24 C23 120.1(4) . . ? C30 C25 C26 122.1(3) . . ? C30 C25 N2 119.1(3) . . ? C26 C25 N2 118.7(3) . . ? C27 C26 C25 116.9(3) . . ? C27 C26 C31 120.6(3) . . ? C25 C26 C31 122.6(3) . . ? C28 C27 C26 122.3(3) . . ? C29 C28 C27 118.3(3) . . ? C29 C28 C32 121.4(4) . . ? C27 C28 C32 120.2(4) . . ? C28 C29 C30 122.3(3) . . ? C25 C30 C29 118.0(3) . . ? C25 C30 C33 122.7(3) . . ? C29 C30 C33 119.3(3) . . ? N4 C34 N3 115.3(3) . . ? C52 C35 N3 109.7(2) . . ? C52 C35 C46 112.3(2) . . ? N3 C35 C46 110.4(2) . . ? C52 C35 C36 115.8(2) . . ? N3 C35 C36 99.4(2) . . ? C46 C35 C36 108.5(2) . . ? N4 C36 C35 103.9(2) . . ? C38 C37 C42 121.3(3) . . ? C38 C37 N3 120.2(3) . . ? C42 C37 N3 118.4(2) . . ? C39 C38 C37 117.4(3) . . ? C39 C38 C43 119.8(3) . . ? C37 C38 C43 122.8(3) . . ? C40 C39 C38 123.2(3) . . ? C39 C40 C41 117.6(3) . . ? C39 C40 C44 121.2(3) . . ? C41 C40 C44 121.2(4) . . ? C40 C41 C42 122.4(3) . . ? C41 C42 C37 117.9(3) . . ? C41 C42 C45 118.2(3) . . ? C37 C42 C45 123.9(3) . . ? C51 C46 C47 118.0(3) . . ? C51 C46 C35 121.5(3) . . ? C47 C46 C35 120.2(3) . . ? C48 C47 C46 120.5(3) . . ? C47 C48 C49 121.1(4) . . ? C50 C49 C48 119.3(4) . . ? C49 C50 C51 120.4(4) . . ? C46 C51 C50 120.6(3) . . ? C57 C52 C53 117.8(3) . . ? C57 C52 C35 122.6(3) . . ? C53 C52 C35 119.7(2) . . ? C54 C53 C52 121.2(3) . . ? C55 C54 C53 120.0(3) . . ? C54 C55 C56 119.7(3) . . ? C55 C56 C57 120.4(3) . . ? C56 C57 C52 120.9(3) . . ? C59 C58 C63 122.5(3) . . ? C59 C58 N4 119.0(3) . . ? C63 C58 N4 118.4(3) . . ? C58 C59 C60 116.3(3) . . ? C58 C59 C64 122.7(3) . . ? C60 C59 C64 121.0(3) . . ? C61 C60 C59 123.2(4) . . ? C60 C61 C62 118.1(3) . . ? C60 C61 C65 121.2(4) . . ? C62 C61 C65 120.7(4) . . ? C61 C62 C63 122.8(4) . . ? C62 C63 C58 117.1(3) . . ? C62 C63 C66 119.9(3) . . ? C58 C63 C66 122.9(3) . . ? F2 C67 F1 107.9(5) . . ? F2 C67 F3 105.9(7) . . ? F1 C67 F3 109.2(6) . . ? F2 C67 S1 114.1(4) . . ? F1 C67 S1 109.8(5) . . ? F3 C67 S1 109.7(4) . . ? F5 C68 F6 109.1(5) . . ? F5 C68 F4 105.0(6) . . ? F6 C68 F4 107.4(6) . . ? F5 C68 S2 113.9(5) . . ? F6 C68 S2 112.0(4) . . ? F4 C68 S2 109.0(4) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.620 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.074 data_a11230a _database_code_depnum_ccdc_archive 'CCDC 887383' #TrackingRef 'web_deposit_cif_file_5_JunZhang_1340017342.a11230a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H35 F3 N2 O3 S' _chemical_formula_weight 608.70 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.301(4) _cell_length_b 16.385(8) _cell_length_c 20.954(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.758(7) _cell_angle_gamma 90.00 _cell_volume 3126(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 750 _cell_measurement_theta_min 2.342 _cell_measurement_theta_max 25.512 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9615 _exptl_absorpt_correction_T_max 0.9767 _exptl_absorpt_process_details sadabs _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_% 3.09 _diffrn_reflns_number 12757 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5482 _reflns_number_gt 2851 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0659P)^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 5482 _refine_ls_number_parameters 398 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1247 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _refine_ls_shift/su_max 0.006 _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 0.87461(10) 0.73313(6) 0.44565(4) 0.0605(3) Uani 1 1 d . . . N1 N 0.6560(2) 0.22666(15) 0.14031(11) 0.0414(6) Uani 1 1 d . . . N2 N 0.6800(3) 0.35802(14) 0.12382(11) 0.0414(6) Uani 1 1 d . . . F1 F 0.8368(3) 0.68720(19) 0.55932(13) 0.1246(10) Uani 1 1 d . . . F2 F 0.7401(5) 0.6109(2) 0.48393(16) 0.1764(17) Uani 1 1 d . . . F3 F 0.9702(4) 0.6106(2) 0.51984(18) 0.1727(16) Uani 1 1 d . . . O1 O 1.0042(3) 0.77405(18) 0.47478(13) 0.0946(9) Uani 1 1 d . . . O2 O 0.8889(3) 0.6875(2) 0.38965(13) 0.0995(10) Uani 1 1 d . . . O3 O 0.7434(3) 0.77804(19) 0.43921(14) 0.1009(10) Uani 1 1 d . . . C1 C 0.5930(3) 0.29462(19) 0.11769(14) 0.0398(7) Uani 1 1 d D . . H1 H 0.497(2) 0.2975(15) 0.0973(12) 0.038(8) Uiso 1 1 d D . . C2 C 0.8162(3) 0.24033(18) 0.16757(14) 0.0441(8) Uani 1 1 d . . . H2 H 0.8715 0.2084 0.1412 0.053 Uiso 1 1 calc R . . C3 C 0.8348(3) 0.33196(18) 0.15179(15) 0.0446(8) Uani 1 1 d . . . H3 H 0.8900 0.3347 0.1167 0.054 Uiso 1 1 calc R . . C4 C 0.5882(3) 0.14730(17) 0.13656(14) 0.0412(7) Uani 1 1 d . . . C5 C 0.6262(3) 0.09083(18) 0.09294(14) 0.0439(8) Uani 1 1 d . . . C6 C 0.5678(3) 0.01297(19) 0.09239(15) 0.0501(8) Uani 1 1 d . . . H6 H 0.5912 -0.0253 0.0634 0.060 Uiso 1 1 calc R . . C7 C 0.4766(4) -0.00961(19) 0.13332(16) 0.0527(9) Uani 1 1 d . . . C8 C 0.4385(4) 0.0489(2) 0.17443(16) 0.0562(9) Uani 1 1 d . . . H8 H 0.3747 0.0345 0.2015 0.067 Uiso 1 1 calc R . . C9 C 0.4913(3) 0.12765(19) 0.17695(15) 0.0466(8) Uani 1 1 d . . . C10 C 0.7248(4) 0.1118(2) 0.04693(16) 0.0646(10) Uani 1 1 d . . . H10A H 0.7049 0.1665 0.0312 0.097 Uiso 1 1 calc R . . H10B H 0.7072 0.0745 0.0108 0.097 Uiso 1 1 calc R . . H10C H 0.8254 0.1077 0.0693 0.097 Uiso 1 1 calc R . . C11 C 0.4196(4) -0.0960(2) 0.13273(19) 0.0772(12) Uani 1 1 d . . . H11A H 0.4563 -0.1274 0.1008 0.116 Uiso 1 1 calc R . . H11B H 0.3142 -0.0955 0.1221 0.116 Uiso 1 1 calc R . . H11C H 0.4521 -0.1201 0.1750 0.116 Uiso 1 1 calc R . . C12 C 0.4361(4) 0.1881(2) 0.22056(17) 0.0653(10) Uani 1 1 d . . . H12A H 0.4935 0.2372 0.2233 0.098 Uiso 1 1 calc R . . H12B H 0.4447 0.1651 0.2633 0.098 Uiso 1 1 calc R . . H12C H 0.3350 0.2006 0.2028 0.098 Uiso 1 1 calc R . . C13 C 0.8627(3) 0.21192(18) 0.23714(15) 0.0464(8) Uani 1 1 d . . . C14 C 0.9768(4) 0.1582(2) 0.25160(18) 0.0774(12) Uani 1 1 d . . . H14 H 1.0218 0.1398 0.2185 0.093 Uiso 1 1 calc R . . C15 C 1.0266(6) 0.1306(3) 0.3145(2) 0.1090(18) Uani 1 1 d . . . H15 H 1.1034 0.0933 0.3234 0.131 Uiso 1 1 calc R . . C16 C 0.9631(6) 0.1583(3) 0.3635(2) 0.0938(15) Uani 1 1 d . . . H16 H 0.9963 0.1397 0.4059 0.113 Uiso 1 1 calc R . . C17 C 0.8509(5) 0.2133(3) 0.35033(18) 0.0764(12) Uani 1 1 d . . . H17 H 0.8089 0.2331 0.3839 0.092 Uiso 1 1 calc R . . C18 C 0.7998(4) 0.2394(2) 0.28725(17) 0.0601(9) Uani 1 1 d . . . H18 H 0.7218 0.2760 0.2784 0.072 Uiso 1 1 calc R . . C19 C 0.9150(3) 0.38228(19) 0.20711(15) 0.0463(8) Uani 1 1 d . . . C20 C 1.0665(4) 0.3750(3) 0.22159(19) 0.0763(11) Uani 1 1 d . . . H20 H 1.1144 0.3451 0.1945 0.092 Uiso 1 1 calc R . . C21 C 1.1453(5) 0.4124(3) 0.2763(2) 0.0941(14) Uani 1 1 d . . . H21 H 1.2470 0.4076 0.2858 0.113 Uiso 1 1 calc R . . C22 C 1.0779(5) 0.4562(3) 0.3169(2) 0.0803(12) Uani 1 1 d . . . H22 H 1.1329 0.4801 0.3543 0.096 Uiso 1 1 calc R . . C23 C 0.9300(4) 0.4646(2) 0.30246(17) 0.0695(11) Uani 1 1 d . . . H23 H 0.8831 0.4953 0.3295 0.083 Uiso 1 1 calc R . . C24 C 0.8492(4) 0.4277(2) 0.24778(16) 0.0591(9) Uani 1 1 d . . . H24 H 0.7477 0.4338 0.2383 0.071 Uiso 1 1 calc R . . C25 C 0.6328(3) 0.44064(17) 0.10608(13) 0.0422(8) Uani 1 1 d . . . C26 C 0.5177(3) 0.47424(18) 0.13158(14) 0.0434(8) Uani 1 1 d . . . C27 C 0.4796(4) 0.5541(2) 0.11657(16) 0.0557(9) Uani 1 1 d . . . H27 H 0.4035 0.5770 0.1333 0.067 Uiso 1 1 calc R . . C28 C 0.5489(4) 0.60137(19) 0.07805(17) 0.0555(9) Uani 1 1 d . . . C29 C 0.6595(4) 0.5657(2) 0.05228(15) 0.0530(9) Uani 1 1 d . . . H29 H 0.7066 0.5967 0.0255 0.064 Uiso 1 1 calc R . . C30 C 0.7021(3) 0.48584(19) 0.06511(14) 0.0458(8) Uani 1 1 d . . . C31 C 0.4331(4) 0.4275(2) 0.17396(16) 0.0598(9) Uani 1 1 d . . . H31A H 0.3870 0.4652 0.1986 0.090 Uiso 1 1 calc R . . H31B H 0.4991 0.3929 0.2032 0.090 Uiso 1 1 calc R . . H31C H 0.3593 0.3947 0.1470 0.090 Uiso 1 1 calc R . . C32 C 0.5084(5) 0.6896(2) 0.0646(2) 0.0847(13) Uani 1 1 d . . . H32A H 0.4072 0.6934 0.0430 0.127 Uiso 1 1 calc R . . H32B H 0.5691 0.7126 0.0372 0.127 Uiso 1 1 calc R . . H32C H 0.5231 0.7192 0.1049 0.127 Uiso 1 1 calc R . . C33 C 0.8226(4) 0.4517(2) 0.03341(17) 0.0673(10) Uani 1 1 d . . . H33A H 0.8308 0.4845 -0.0036 0.101 Uiso 1 1 calc R . . H33B H 0.7987 0.3966 0.0195 0.101 Uiso 1 1 calc R . . H33C H 0.9142 0.4523 0.0643 0.101 Uiso 1 1 calc R . . C34 C 0.8549(5) 0.6547(3) 0.5036(2) 0.0817(12) 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 0.0482(5) 0.0792(7) 0.0561(6) 0.0108(5) 0.0155(4) -0.0048(5) N1 0.0376(14) 0.0436(16) 0.0429(15) -0.0016(12) 0.0081(11) -0.0022(12) N2 0.0366(15) 0.0410(15) 0.0464(15) 0.0015(12) 0.0083(11) -0.0032(12) F1 0.141(3) 0.169(3) 0.0726(18) 0.0265(18) 0.0431(17) -0.011(2) F2 0.198(3) 0.185(3) 0.137(3) 0.032(2) 0.013(2) -0.130(3) F3 0.175(3) 0.166(3) 0.197(4) 0.106(3) 0.086(3) 0.079(3) O1 0.0752(19) 0.117(2) 0.092(2) 0.0069(17) 0.0170(16) -0.0460(17) O2 0.095(2) 0.144(3) 0.0649(19) -0.0156(17) 0.0303(16) -0.0011(18) O3 0.080(2) 0.121(2) 0.104(2) 0.0322(18) 0.0250(17) 0.0399(18) C1 0.0373(19) 0.045(2) 0.0379(18) -0.0024(14) 0.0092(15) -0.0007(17) C2 0.0371(17) 0.0502(19) 0.0444(18) -0.0014(14) 0.0068(14) 0.0023(15) C3 0.0367(18) 0.0499(19) 0.0483(19) 0.0030(15) 0.0108(14) 0.0011(15) C4 0.0405(18) 0.0399(18) 0.0409(18) 0.0023(14) 0.0026(14) -0.0001(14) C5 0.0431(19) 0.0441(19) 0.0428(19) 0.0016(15) 0.0050(15) -0.0006(15) C6 0.051(2) 0.048(2) 0.048(2) -0.0054(15) 0.0012(16) 0.0052(16) C7 0.059(2) 0.048(2) 0.049(2) 0.0048(16) 0.0051(17) -0.0093(17) C8 0.056(2) 0.060(2) 0.054(2) 0.0058(18) 0.0141(17) -0.0125(18) C9 0.045(2) 0.049(2) 0.0462(19) 0.0007(15) 0.0106(15) -0.0039(16) C10 0.072(3) 0.071(2) 0.055(2) -0.0086(18) 0.0232(19) -0.0076(19) C11 0.102(3) 0.055(2) 0.074(3) 0.0022(19) 0.018(2) -0.022(2) C12 0.060(2) 0.074(3) 0.068(2) -0.0074(19) 0.0287(19) -0.0081(19) C13 0.046(2) 0.0410(19) 0.049(2) -0.0001(15) 0.0034(16) -0.0003(15) C14 0.095(3) 0.073(3) 0.057(2) 0.000(2) -0.001(2) 0.031(2) C15 0.139(5) 0.105(4) 0.071(3) 0.006(3) -0.009(3) 0.058(3) C16 0.123(4) 0.087(3) 0.059(3) 0.010(2) -0.009(3) 0.014(3) C17 0.095(3) 0.087(3) 0.049(2) -0.001(2) 0.019(2) -0.012(3) C18 0.052(2) 0.068(2) 0.060(2) 0.0030(19) 0.0119(18) -0.0012(18) C19 0.0358(19) 0.049(2) 0.054(2) 0.0009(16) 0.0097(15) -0.0060(15) C20 0.046(2) 0.109(3) 0.075(3) -0.015(2) 0.0146(19) -0.012(2) C21 0.050(3) 0.134(4) 0.093(3) -0.015(3) 0.003(2) -0.024(3) C22 0.066(3) 0.095(3) 0.073(3) -0.017(2) -0.001(2) -0.031(2) C23 0.064(3) 0.076(3) 0.064(2) -0.013(2) 0.004(2) -0.015(2) C24 0.052(2) 0.062(2) 0.062(2) -0.0056(18) 0.0097(18) -0.0046(18) C25 0.0469(19) 0.0400(18) 0.0378(18) -0.0006(14) 0.0044(15) -0.0052(15) C26 0.0406(18) 0.047(2) 0.0434(18) -0.0044(14) 0.0106(15) -0.0005(15) C27 0.055(2) 0.052(2) 0.063(2) -0.0039(17) 0.0181(17) 0.0092(18) C28 0.059(2) 0.045(2) 0.061(2) 0.0018(17) 0.0079(18) 0.0025(17) C29 0.055(2) 0.052(2) 0.052(2) 0.0066(16) 0.0118(17) -0.0080(17) C30 0.0421(19) 0.047(2) 0.0490(19) 0.0005(15) 0.0106(15) -0.0020(15) C31 0.055(2) 0.065(2) 0.066(2) -0.0031(18) 0.0279(18) 0.0006(18) C32 0.108(4) 0.054(2) 0.100(3) 0.010(2) 0.040(3) 0.015(2) C33 0.070(3) 0.069(2) 0.072(2) 0.019(2) 0.036(2) 0.008(2) C34 0.064(3) 0.106(4) 0.078(3) 0.016(3) 0.020(2) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.405(3) . ? S1 O3 1.408(3) . ? S1 O2 1.420(3) . ? S1 C34 1.804(4) . ? N1 C1 1.302(4) . ? N1 C4 1.440(4) . ? N1 C2 1.499(3) . ? N2 C1 1.307(4) . ? N2 C25 1.448(4) . ? N2 C3 1.502(4) . ? F1 C34 1.324(5) . ? F2 C34 1.283(5) . ? F3 C34 1.280(5) . ? C2 C13 1.507(4) . ? C2 C3 1.554(4) . ? C3 C19 1.493(4) . ? C4 C9 1.394(4) . ? C4 C5 1.396(4) . ? C5 C6 1.385(4) . ? C5 C10 1.500(4) . ? C6 C7 1.375(4) . ? C7 C8 1.382(4) . ? C7 C11 1.511(4) . ? C8 C9 1.378(4) . ? C9 C12 1.507(4) . ? C13 C14 1.365(4) . ? C13 C18 1.378(5) . ? C14 C15 1.380(5) . ? C15 C16 1.362(6) . ? C16 C17 1.363(6) . ? C17 C18 1.379(5) . ? C19 C24 1.367(4) . ? C19 C20 1.385(4) . ? C20 C21 1.372(5) . ? C21 C22 1.361(6) . ? C22 C23 1.354(5) . ? C23 C24 1.375(4) . ? C25 C30 1.388(4) . ? C25 C26 1.403(4) . ? C26 C27 1.375(4) . ? C26 C31 1.510(4) . ? C27 C28 1.371(5) . ? C28 C29 1.385(5) . ? C28 C32 1.506(4) . ? C29 C30 1.378(4) . ? C30 C33 1.520(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 O1 S1 O3 116.3(2) . . ? O1 S1 O2 113.16(19) . . ? O3 S1 O2 114.92(19) . . ? O1 S1 C34 104.08(19) . . ? O3 S1 C34 103.4(2) . . ? O2 S1 C34 102.8(2) . . ? C1 N1 C4 126.3(2) . . ? C1 N1 C2 110.5(2) . . ? C4 N1 C2 123.1(2) . . ? C1 N2 C25 124.7(3) . . ? C1 N2 C3 109.7(2) . . ? C25 N2 C3 125.6(2) . . ? N1 C1 N2 114.8(3) . . ? N1 C2 C13 112.9(2) . . ? N1 C2 C3 102.0(2) . . ? C13 C2 C3 118.8(2) . . ? C19 C3 N2 115.7(2) . . ? C19 C3 C2 115.3(2) . . ? N2 C3 C2 102.6(2) . . ? C9 C4 C5 121.7(3) . . ? C9 C4 N1 120.4(3) . . ? C5 C4 N1 117.9(3) . . ? C6 C5 C4 117.7(3) . . ? C6 C5 C10 119.7(3) . . ? C4 C5 C10 122.6(3) . . ? C7 C6 C5 122.2(3) . . ? C6 C7 C8 118.1(3) . . ? C6 C7 C11 120.5(3) . . ? C8 C7 C11 121.4(3) . . ? C9 C8 C7 122.6(3) . . ? C8 C9 C4 117.5(3) . . ? C8 C9 C12 118.5(3) . . ? C4 C9 C12 123.9(3) . . ? C14 C13 C18 118.3(3) . . ? C14 C13 C2 118.1(3) . . ? C18 C13 C2 123.6(3) . . ? C13 C14 C15 121.2(4) . . ? C16 C15 C14 119.9(4) . . ? C15 C16 C17 119.9(4) . . ? C16 C17 C18 120.0(4) . . ? C13 C18 C17 120.8(4) . . ? C24 C19 C20 118.4(3) . . ? C24 C19 C3 124.7(3) . . ? C20 C19 C3 116.6(3) . . ? C21 C20 C19 119.4(4) . . ? C22 C21 C20 121.5(4) . . ? C23 C22 C21 119.3(4) . . ? C22 C23 C24 120.0(4) . . ? C19 C24 C23 121.4(3) . . ? C30 C25 C26 120.9(3) . . ? C30 C25 N2 120.2(3) . . ? C26 C25 N2 118.9(3) . . ? C27 C26 C25 117.9(3) . . ? C27 C26 C31 118.4(3) . . ? C25 C26 C31 123.7(3) . . ? C28 C27 C26 122.8(3) . . ? C27 C28 C29 117.8(3) . . ? C27 C28 C32 121.6(3) . . ? C29 C28 C32 120.6(3) . . ? C30 C29 C28 122.1(3) . . ? C29 C30 C25 118.4(3) . . ? C29 C30 C33 118.2(3) . . ? C25 C30 C33 123.4(3) . . ? F3 C34 F2 111.6(5) . . ? F3 C34 F1 104.1(4) . . ? F2 C34 F1 105.2(4) . . ? F3 C34 S1 112.7(3) . . ? F2 C34 S1 111.9(3) . . ? F1 C34 S1 110.8(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O3 0.907(16) 2.236(18) 3.125(4) 166(2) 2_645 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.284 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.041