# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1048 loop_ _publ_author_name 'Ning Ma.' 'Tu, Shujiang Tu.' 'Wever, Walter' 'Guigen Li.' _publ_contact_author_name 'Guigen Li' _publ_contact_author_address ; Box 41061 Lubbock Texas United States TX 79409-1061 ; _publ_contact_author_email guigen.li@ttu.edu # Attachment '- 4g.cif' data_100201a _database_code_depnum_ccdc_archive 'CCDC 776624' #TrackingRef '- 4g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 F2 N2 O6 S' _chemical_formula_weight 532.55 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' O O 0.0106 0.0060 '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' 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 14.6241(13) _cell_length_b 20.681(2) _cell_length_c 8.7450(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.5380(10) _cell_angle_gamma 90.00 _cell_volume 2644.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1028 _cell_measurement_theta_min 2.529 _cell_measurement_theta_max 27.353 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 13700 _diffrn_reflns_av_R_equivalents 0.1601 _diffrn_reflns_av_sigmaI/netI 0.2023 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4637 _reflns_number_gt 1527 _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^)+(0.0389P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4637 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2589 _refine_ls_R_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.4334(2) 0.26806(15) 0.7387(5) 0.1037(16) Uani 0.882(9) 1 d P A 1 S1' S 0.4363(16) 0.2353(11) 0.608(4) 0.104(12) Uani 0.118(9) 1 d P A 2 F1 F 0.0945(3) 0.7421(2) 0.1612(5) 0.143(2) Uani 1 1 d . . . F2 F 0.1198(3) 0.3295(2) 1.0907(5) 0.1274(17) Uani 1 1 d . . . N1 N 0.4655(3) 0.4745(3) 0.2098(6) 0.0649(15) Uani 1 1 d . . . N2 N 0.3660(3) 0.4345(2) 0.5630(6) 0.0621(14) Uani 1 1 d . . . H2 H 0.3713 0.3935 0.5764 0.075 Uiso 1 1 calc R . . O1 O 0.4488(3) 0.43048(18) 0.3329(5) 0.0605(12) Uani 1 1 d . . . O2 O 0.1018(3) 0.5123(2) 0.5676(5) 0.0746(14) Uani 1 1 d . . . O3 O 0.1534(3) 0.5845(2) 0.7618(5) 0.0788(14) Uani 1 1 d . . . O4 O 0.1928(2) 0.46331(18) 0.4143(4) 0.0524(11) Uani 1 1 d . . . O5 O 0.2965(3) 0.60564(19) 0.8003(5) 0.0641(13) Uani 1 1 d . . . O6 O 0.4344(4) 0.3079(2) 0.5967(6) 0.1147(19) Uani 1 1 d . . . C1 C 0.4400(4) 0.5845(3) 0.1406(7) 0.078(2) Uani 1 1 d . . . H1A H 0.4960 0.5792 0.0856 0.116 Uiso 1 1 calc R . . H1B H 0.4429 0.6235 0.2000 0.116 Uiso 1 1 calc R . . H1C H 0.3897 0.5870 0.0695 0.116 Uiso 1 1 calc R . . C2 C 0.4266(4) 0.5277(3) 0.2452(8) 0.0642(19) Uani 1 1 d . . . C3 C 0.3797(4) 0.5241(3) 0.3877(8) 0.0543(17) Uani 1 1 d . . . C4 C 0.3961(4) 0.4635(3) 0.4352(8) 0.0569(17) Uani 1 1 d . . . C5 C 0.3255(4) 0.5709(3) 0.4811(6) 0.0471(15) Uani 1 1 d . . . H5 H 0.3692 0.5966 0.5410 0.057 Uiso 1 1 calc R . . C6 C 0.2662(4) 0.5307(3) 0.5987(6) 0.0424(15) Uani 1 1 d . . . C7 C 0.3252(4) 0.4749(3) 0.6749(7) 0.0495(16) Uani 1 1 d . . . H7 H 0.3749 0.4956 0.7328 0.059 Uiso 1 1 calc R . . C8 C 0.1860(4) 0.5005(3) 0.5179(7) 0.0466(16) Uani 1 1 d . . . C9 C 0.2415(5) 0.5765(3) 0.7266(7) 0.0493(17) Uani 1 1 d . . . C10 C 0.0759(4) 0.5582(3) 0.6796(8) 0.0581(18) Uani 1 1 d . . . C11 C 0.0282(4) 0.6129(3) 0.6016(7) 0.073(2) Uani 1 1 d . . . H11A H 0.0677 0.6314 0.5263 0.110 Uiso 1 1 calc R . . H11B H 0.0127 0.6453 0.6757 0.110 Uiso 1 1 calc R . . H11C H -0.0265 0.5973 0.5527 0.110 Uiso 1 1 calc R . . C12 C 0.0198(4) 0.5228(3) 0.7931(7) 0.078(2) Uani 1 1 d . . . H12A H -0.0335 0.5054 0.7432 0.117 Uiso 1 1 calc R . . H12B H 0.0014 0.5520 0.8724 0.117 Uiso 1 1 calc R . . H12C H 0.0552 0.4883 0.8368 0.117 Uiso 1 1 calc R . . C13 C 0.2672(4) 0.6178(3) 0.3891(8) 0.0524(16) Uani 1 1 d . . . C14 C 0.2594(4) 0.6813(3) 0.4345(7) 0.0627(19) Uani 1 1 d . . . H14 H 0.2924 0.6959 0.5191 0.075 Uiso 1 1 calc R . . C15 C 0.2025(6) 0.7236(3) 0.3548(10) 0.081(2) Uani 1 1 d . . . H15 H 0.1987 0.7669 0.3832 0.097 Uiso 1 1 calc R . . C16 C 0.1530(6) 0.7009(4) 0.2357(11) 0.082(2) Uani 1 1 d . . . C17 C 0.1609(5) 0.6396(4) 0.1818(8) 0.077(2) Uani 1 1 d . . . H17 H 0.1286 0.6262 0.0953 0.093 Uiso 1 1 calc R . . C18 C 0.2182(4) 0.5980(3) 0.2589(8) 0.0601(18) Uani 1 1 d . . . H18 H 0.2246 0.5557 0.2240 0.072 Uiso 1 1 calc R . . C19 C 0.2710(4) 0.4345(3) 0.7866(7) 0.0504(16) Uani 1 1 d . . . C20 C 0.2732(4) 0.4491(3) 0.9397(8) 0.0638(19) Uani 1 1 d . . . H20 H 0.3099 0.4828 0.9747 0.077 Uiso 1 1 calc R . . C21 C 0.2217(5) 0.4141(4) 1.0428(8) 0.079(2) Uani 1 1 d . . . H21 H 0.2233 0.4241 1.1465 0.094 Uiso 1 1 calc R . . C22 C 0.1684(6) 0.3646(4) 0.9889(11) 0.080(2) Uani 1 1 d . . . C23 C 0.1651(5) 0.3486(3) 0.8395(10) 0.078(2) Uani 1 1 d . . . H23 H 0.1289 0.3144 0.8055 0.094 Uiso 1 1 calc R . . C24 C 0.2167(4) 0.3841(3) 0.7379(7) 0.0624(18) Uani 1 1 d . . . H24 H 0.2146 0.3737 0.6344 0.075 Uiso 1 1 calc R . . C25 C 0.3483(6) 0.2121(3) 0.7214(11) 0.132(3) Uani 1 1 d . . . H25A H 0.2901 0.2332 0.7284 0.198 Uiso 0.882(9) 1 calc PR A 1 H25B H 0.3542 0.1808 0.8020 0.198 Uiso 0.882(9) 1 calc PR A 1 H25C H 0.3528 0.1908 0.6243 0.198 Uiso 0.882(9) 1 calc PR A 1 H25D H 0.3110 0.2487 0.7472 0.198 Uiso 0.118(9) 1 d PR A 2 H25E H 0.3724 0.1929 0.8133 0.198 Uiso 0.118(9) 1 d PR A 2 H25F H 0.3120 0.1809 0.6671 0.198 Uiso 0.118(9) 1 d PR A 2 C26 C 0.5263(5) 0.2182(3) 0.7249(11) 0.134(3) Uani 1 1 d . . . H26A H 0.5813 0.2433 0.7342 0.201 Uiso 0.882(9) 1 calc PR A 1 H26B H 0.5251 0.1968 0.6275 0.201 Uiso 0.882(9) 1 calc PR A 1 H26C H 0.5247 0.1866 0.8052 0.201 Uiso 0.882(9) 1 calc PR A 1 H26D H 0.5754 0.2479 0.7058 0.201 Uiso 0.118(9) 1 d PR A 2 H26E H 0.5464 0.1749 0.7046 0.201 Uiso 0.118(9) 1 d PR A 2 H26F H 0.5081 0.2216 0.8298 0.201 Uiso 0.118(9) 1 d PR A 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 S1 0.135(3) 0.0567(18) 0.119(3) 0.010(2) -0.0306(19) -0.0052(17) S1' 0.14(2) 0.057(14) 0.12(3) 0.010(15) -0.031(16) -0.005(12) F1 0.177(5) 0.124(4) 0.129(4) 0.057(3) 0.030(4) 0.082(3) F2 0.161(4) 0.112(3) 0.111(4) 0.033(3) 0.072(3) -0.003(3) N1 0.073(4) 0.064(4) 0.058(4) -0.013(3) 0.012(3) 0.004(3) N2 0.070(4) 0.052(3) 0.065(4) -0.003(3) 0.009(3) 0.006(3) O1 0.063(3) 0.048(3) 0.070(3) -0.012(3) 0.011(3) 0.013(2) O2 0.048(3) 0.092(3) 0.084(3) -0.050(3) 0.001(3) 0.006(2) O3 0.052(3) 0.109(4) 0.075(3) -0.052(3) 0.004(3) 0.005(3) O4 0.055(3) 0.056(3) 0.045(3) -0.012(2) 0.007(2) -0.005(2) O5 0.057(3) 0.069(3) 0.066(3) -0.024(2) -0.006(2) -0.001(2) O6 0.166(5) 0.066(4) 0.112(5) 0.017(3) -0.004(4) 0.026(3) C1 0.104(6) 0.067(5) 0.062(5) 0.001(4) 0.009(4) -0.010(4) C2 0.067(5) 0.062(5) 0.064(5) -0.001(4) 0.000(4) -0.004(4) C3 0.053(4) 0.054(4) 0.056(5) -0.003(4) 0.001(4) -0.002(3) C4 0.056(4) 0.054(5) 0.061(5) -0.003(4) 0.008(4) 0.004(4) C5 0.051(4) 0.043(4) 0.048(4) -0.009(3) 0.008(3) 0.002(3) C6 0.042(4) 0.041(3) 0.045(4) -0.013(3) 0.004(3) 0.001(3) C7 0.051(4) 0.054(4) 0.044(4) -0.011(3) 0.007(3) 0.010(3) C8 0.052(4) 0.045(4) 0.043(4) -0.007(3) 0.010(4) 0.009(3) C9 0.048(4) 0.051(4) 0.049(5) -0.007(3) 0.008(4) 0.007(4) C10 0.041(4) 0.072(5) 0.061(5) -0.019(4) -0.002(4) -0.002(4) C11 0.071(5) 0.071(5) 0.078(5) 0.002(4) 0.000(4) -0.007(4) C12 0.082(5) 0.089(5) 0.063(5) 0.001(4) 0.002(4) 0.011(4) C13 0.062(4) 0.044(4) 0.052(5) -0.005(4) 0.020(4) 0.008(4) C14 0.080(5) 0.045(4) 0.064(5) -0.005(4) 0.021(4) 0.005(4) C15 0.111(7) 0.046(5) 0.087(6) 0.013(5) 0.037(5) 0.024(5) C16 0.092(6) 0.072(6) 0.084(7) 0.027(5) 0.021(5) 0.033(5) C17 0.089(6) 0.073(5) 0.071(5) 0.015(5) 0.010(4) 0.016(5) C18 0.072(5) 0.048(4) 0.060(5) 0.004(4) 0.007(4) 0.017(4) C19 0.054(4) 0.049(4) 0.048(5) -0.004(4) 0.002(4) 0.009(3) C20 0.076(5) 0.060(4) 0.055(5) -0.002(4) 0.004(4) 0.008(4) C21 0.103(6) 0.079(6) 0.055(5) 0.000(5) 0.012(5) 0.022(5) C22 0.094(6) 0.077(6) 0.070(6) 0.025(5) 0.026(5) 0.011(5) C23 0.092(6) 0.068(5) 0.076(6) 0.011(5) 0.015(5) -0.005(4) C24 0.078(5) 0.060(4) 0.049(5) -0.001(4) 0.005(4) -0.001(4) C25 0.123(8) 0.087(6) 0.185(10) 0.008(6) -0.045(8) 0.003(6) C26 0.126(8) 0.085(6) 0.192(10) 0.040(6) 0.004(7) 0.000(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 S1 O6 1.489(5) . ? S1 C25 1.705(8) . ? S1 C26 1.711(8) . ? S1 H25D 1.8368 . ? S1 H26F 1.6532 . ? S1' O6 1.50(2) . ? S1' C26 1.69(2) . ? S1' C25 1.70(3) . ? F1 C16 1.369(7) . ? F2 C22 1.355(8) . ? N1 C2 1.277(7) . ? N1 O1 1.433(6) . ? N2 C4 1.346(7) . ? N2 C7 1.423(6) . ? N2 H2 0.8600 . ? O1 C4 1.368(7) . ? O2 C8 1.332(6) . ? O2 C10 1.418(6) . ? O3 C9 1.337(6) . ? O3 C10 1.443(6) . ? O4 C8 1.193(6) . ? O5 C9 1.190(6) . ? C1 C2 1.503(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.430(8) . ? C3 C4 1.340(7) . ? C3 C5 1.498(7) . ? C5 C13 1.518(7) . ? C5 C6 1.586(7) . ? C5 H5 0.9800 . ? C6 C8 1.501(7) . ? C6 C9 1.511(7) . ? C6 C7 1.584(7) . ? C7 C19 1.515(8) . ? C7 H7 0.9800 . ? C10 C12 1.486(8) . ? C10 C11 1.491(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.377(7) . ? C13 C18 1.401(7) . ? C14 C15 1.391(8) . ? C14 H14 0.9300 . ? C15 C16 1.348(9) . ? C15 H15 0.9300 . ? C16 C17 1.358(9) . ? C17 C18 1.373(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.372(8) . ? C19 C24 1.376(7) . ? C20 C21 1.384(8) . ? C20 H20 0.9300 . ? C21 C22 1.368(9) . ? C21 H21 0.9300 . ? C22 C23 1.348(9) . ? C23 C24 1.383(8) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C25 H25D 0.9600 . ? C25 H25E 0.9600 . ? C25 H25F 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C26 H26D 0.9600 . ? C26 H26E 0.9600 . ? C26 H26F 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 O6 S1 C25 108.3(4) . . ? O6 S1 C26 105.1(4) . . ? C25 S1 C26 99.5(4) . . ? O6 S1 H25D 99.9 . . ? C25 S1 H25D 31.2 . . ? C26 S1 H25D 130.3 . . ? O6 S1 H26F 135.3 . . ? C25 S1 H26F 97.3 . . ? C26 S1 H26F 33.1 . . ? H25D S1 H26F 119.6 . . ? O6 S1' C26 105.2(16) . . ? O6 S1' C25 107.9(18) . . ? C26 S1' C25 100.4(14) . . ? C2 N1 O1 106.6(5) . . ? C4 N2 C7 116.9(5) . . ? C4 N2 H2 121.5 . . ? C7 N2 H2 121.5 . . ? C4 O1 N1 105.9(4) . . ? C8 O2 C10 127.0(5) . . ? C9 O3 C10 126.3(5) . . ? S1 O6 S1' 52.6(11) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 112.7(6) . . ? N1 C2 C1 117.6(7) . . ? C3 C2 C1 129.6(7) . . ? C4 C3 C2 103.4(6) . . ? C4 C3 C5 121.9(6) . . ? C2 C3 C5 134.6(6) . . ? C3 C4 N2 127.9(7) . . ? C3 C4 O1 111.4(6) . . ? N2 C4 O1 120.7(6) . . ? C3 C5 C13 114.9(5) . . ? C3 C5 C6 108.1(5) . . ? C13 C5 C6 111.7(4) . . ? C3 C5 H5 107.2 . . ? C13 C5 H5 107.2 . . ? C6 C5 H5 107.2 . . ? C8 C6 C9 114.7(5) . . ? C8 C6 C7 108.3(4) . . ? C9 C6 C7 106.1(4) . . ? C8 C6 C5 110.1(5) . . ? C9 C6 C5 106.8(4) . . ? C7 C6 C5 110.8(4) . . ? N2 C7 C19 110.2(5) . . ? N2 C7 C6 111.6(5) . . ? C19 C7 C6 112.8(5) . . ? N2 C7 H7 107.3 . . ? C19 C7 H7 107.3 . . ? C6 C7 H7 107.3 . . ? O4 C8 O2 116.8(6) . . ? O4 C8 C6 123.7(6) . . ? O2 C8 C6 119.4(5) . . ? O5 C9 O3 117.4(5) . . ? O5 C9 C6 123.5(6) . . ? O3 C9 C6 119.1(6) . . ? O2 C10 O3 112.5(5) . . ? O2 C10 C12 106.5(5) . . ? O3 C10 C12 106.8(5) . . ? O2 C10 C11 108.6(5) . . ? O3 C10 C11 107.7(5) . . ? C12 C10 C11 114.8(5) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.0(6) . . ? C14 C13 C5 120.3(6) . . ? C18 C13 C5 121.6(5) . . ? C13 C14 C15 120.5(6) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 118.8(7) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 123.2(8) . . ? C15 C16 F1 118.6(8) . . ? C17 C16 F1 118.1(9) . . ? C16 C17 C18 117.9(7) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? C17 C18 C13 121.4(6) . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 119.3 . . ? C20 C19 C24 118.5(6) . . ? C20 C19 C7 120.1(6) . . ? C24 C19 C7 121.5(6) . . ? C19 C20 C21 120.9(7) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 118.6(7) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C23 C22 F2 119.4(9) . . ? C23 C22 C21 122.2(8) . . ? F2 C22 C21 118.4(9) . . ? C22 C23 C24 118.5(7) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? C19 C24 C23 121.4(6) . . ? C19 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? S1' C25 S1 45.9(10) . . ? S1' C25 H25A 125.9 . . ? S1 C25 H25A 109.5 . . ? S1' C25 H25B 123.7 . . ? S1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S1' C25 H25C 63.6 . . ? S1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? S1' C25 H25D 110.5 . . ? S1 C25 H25D 82.0 . . ? H25A C25 H25D 28.4 . . ? H25B C25 H25D 113.9 . . ? H25C C25 H25D 127.8 . . ? S1' C25 H25E 109.3 . . ? S1 C25 H25E 86.8 . . ? H25A C25 H25E 117.0 . . ? H25B C25 H25E 22.8 . . ? H25C C25 H25E 121.6 . . ? H25D C25 H25E 109.5 . . ? S1' C25 H25F 108.7 . . ? S1 C25 H25F 154.3 . . ? H25A C25 H25F 81.4 . . ? H25B C25 H25F 87.3 . . ? H25C C25 H25F 45.2 . . ? H25D C25 H25F 109.5 . . ? H25E C25 H25F 109.5 . . ? S1' C26 S1 45.9(10) . . ? S1' C26 H26A 125.8 . . ? S1 C26 H26A 109.5 . . ? S1' C26 H26B 63.6 . . ? S1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? S1' C26 H26C 123.8 . . ? S1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? S1' C26 H26D 109.9 . . ? S1 C26 H26D 102.9 . . ? H26A C26 H26D 16.7 . . ? H26B C26 H26D 98.5 . . ? H26C C26 H26D 125.9 . . ? S1' C26 H26E 108.7 . . ? S1 C26 H26E 145.1 . . ? H26A C26 H26E 105.2 . . ? H26B C26 H26E 53.7 . . ? H26C C26 H26E 60.6 . . ? H26D C26 H26E 109.5 . . ? S1' C26 H26F 109.7 . . ? S1 C26 H26F 70.2 . . ? H26A C26 H26F 96.8 . . ? H26B C26 H26F 151.5 . . ? H26C C26 H26F 48.9 . . ? H26D C26 H26F 109.5 . . ? H26E C26 H26F 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 C2 N1 O1 C4 1.4(6) . . . . ? C25 S1 O6 S1' -51.7(11) . . . . ? C26 S1 O6 S1' 53.9(12) . . . . ? C26 S1' O6 S1 -54.7(12) . . . . ? C25 S1' O6 S1 51.8(13) . . . . ? O1 N1 C2 C3 -1.6(7) . . . . ? O1 N1 C2 C1 175.2(4) . . . . ? N1 C2 C3 C4 1.2(7) . . . . ? C1 C2 C3 C4 -175.1(6) . . . . ? N1 C2 C3 C5 179.2(6) . . . . ? C1 C2 C3 C5 2.9(11) . . . . ? C2 C3 C4 N2 -178.8(6) . . . . ? C5 C3 C4 N2 2.9(10) . . . . ? C2 C3 C4 O1 -0.2(7) . . . . ? C5 C3 C4 O1 -178.5(5) . . . . ? C7 N2 C4 C3 -11.8(9) . . . . ? C7 N2 C4 O1 169.7(5) . . . . ? N1 O1 C4 C3 -0.7(6) . . . . ? N1 O1 C4 N2 178.0(5) . . . . ? C4 C3 C5 C13 -145.8(5) . . . . ? C2 C3 C5 C13 36.4(9) . . . . ? C4 C3 C5 C6 -20.3(7) . . . . ? C2 C3 C5 C6 162.0(6) . . . . ? C3 C5 C6 C8 -75.9(6) . . . . ? C13 C5 C6 C8 51.5(6) . . . . ? C3 C5 C6 C9 159.0(5) . . . . ? C13 C5 C6 C9 -73.6(6) . . . . ? C3 C5 C6 C7 43.9(6) . . . . ? C13 C5 C6 C7 171.3(4) . . . . ? C4 N2 C7 C19 163.4(5) . . . . ? C4 N2 C7 C6 37.2(7) . . . . ? C8 C6 C7 N2 66.4(6) . . . . ? C9 C6 C7 N2 -170.0(5) . . . . ? C5 C6 C7 N2 -54.4(6) . . . . ? C8 C6 C7 C19 -58.3(6) . . . . ? C9 C6 C7 C19 65.3(6) . . . . ? C5 C6 C7 C19 -179.1(5) . . . . ? C10 O2 C8 O4 -174.4(6) . . . . ? C10 O2 C8 C6 9.1(9) . . . . ? C9 C6 C8 O4 179.9(5) . . . . ? C7 C6 C8 O4 -61.8(7) . . . . ? C5 C6 C8 O4 59.5(7) . . . . ? C9 C6 C8 O2 -3.7(7) . . . . ? C7 C6 C8 O2 114.5(5) . . . . ? C5 C6 C8 O2 -124.2(5) . . . . ? C10 O3 C9 O5 174.4(6) . . . . ? C10 O3 C9 C6 -6.4(9) . . . . ? C8 C6 C9 O5 -178.3(5) . . . . ? C7 C6 C9 O5 62.1(7) . . . . ? C5 C6 C9 O5 -56.1(7) . . . . ? C8 C6 C9 O3 2.6(8) . . . . ? C7 C6 C9 O3 -116.9(5) . . . . ? C5 C6 C9 O3 124.8(5) . . . . ? C8 O2 C10 O3 -11.6(9) . . . . ? C8 O2 C10 C12 -128.3(6) . . . . ? C8 O2 C10 C11 107.5(6) . . . . ? C9 O3 C10 O2 10.2(9) . . . . ? C9 O3 C10 C12 126.7(6) . . . . ? C9 O3 C10 C11 -109.5(6) . . . . ? C3 C5 C13 C14 -140.8(5) . . . . ? C6 C5 C13 C14 95.5(6) . . . . ? C3 C5 C13 C18 40.9(7) . . . . ? C6 C5 C13 C18 -82.8(6) . . . . ? C18 C13 C14 C15 1.5(9) . . . . ? C5 C13 C14 C15 -176.8(5) . . . . ? C13 C14 C15 C16 2.2(10) . . . . ? C14 C15 C16 C17 -5.2(11) . . . . ? C14 C15 C16 F1 177.6(6) . . . . ? C15 C16 C17 C18 4.1(11) . . . . ? F1 C16 C17 C18 -178.6(6) . . . . ? C16 C17 C18 C13 -0.1(10) . . . . ? C14 C13 C18 C17 -2.6(9) . . . . ? C5 C13 C18 C17 175.7(5) . . . . ? N2 C7 C19 C20 139.8(5) . . . . ? C6 C7 C19 C20 -94.7(6) . . . . ? N2 C7 C19 C24 -42.1(7) . . . . ? C6 C7 C19 C24 83.4(6) . . . . ? C24 C19 C20 C21 -0.4(9) . . . . ? C7 C19 C20 C21 177.7(5) . . . . ? C19 C20 C21 C22 0.1(10) . . . . ? C20 C21 C22 C23 0.5(10) . . . . ? C20 C21 C22 F2 178.4(6) . . . . ? F2 C22 C23 C24 -178.7(6) . . . . ? C21 C22 C23 C24 -0.8(11) . . . . ? C20 C19 C24 C23 0.1(9) . . . . ? C7 C19 C24 C23 -178.0(6) . . . . ? C22 C23 C24 C19 0.4(10) . . . . ? O6 S1' C25 S1 -49.4(13) . . . . ? C26 S1' C25 S1 60.4(12) . . . . ? O6 S1 C25 S1' 50.3(9) . . . . ? C26 S1 C25 S1' -59.2(10) . . . . ? O6 S1' C26 S1 51.8(13) . . . . ? C25 S1' C26 S1 -60.1(13) . . . . ? O6 S1 C26 S1' -52.6(11) . . . . ? C25 S1 C26 S1' 59.4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.398 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.053