# CCDC 637385 data_publication_text _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'Prof. Dr. Robert Weiss' _publ_contact_author_address ;Institut fuer Organische Chemie der Friedrich-Alexander-Universitaet Erlangen-Nuernberg Henkestrasse 42 D-91054 Erlangen Germany ; _publ_contact_author_email weiss@chemie.uni-erlangen.de loop_ _publ_author_name _publ_author_address 'Weiss, Robert' ;Institut fuer Organische Chemie der Friedrich-Alexander-Universitaet Erlangen-Nuernberg Henkestrasse 42 D-91054 Erlangen Germany ; 'Bess , Matthias' ;Institut fuer Organische Chemie der Friedrich-Alexander-Universitaet Erlangen-Nuernberg Henkestrasse 42 D-91054 Erlangen Germany ; 'Huber, Stefan M.' ;Institut fuer Organische Chemie der Friedrich-Alexander-Universitaet Erlangen-Nuernberg Henkestrasse 42 D-91054 Erlangen Germany ; 'Heinemann, Frank W.' ;Institut fuer Anorganische Chemie der Friedrich-Alexander-Universitaet Erlangen-Nuernberg Egerlandstrasse 1 D-91058 Erlangen Germany ; data_matb10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H23 F3 N2 O8 S' _chemical_formula_weight 568.51 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.4728(4) _cell_length_b 8.5835(2) _cell_length_c 29.13250(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.4790(10) _cell_angle_gamma 90.00 _cell_volume 5114.61(16) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5040 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2352 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type 'empirical (Scalepack)' _exptl_absorpt_correction_T_min 0.9421 _exptl_absorpt_correction_T_max 0.9608 _exptl_absorpt_process_details Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9271 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5771 _reflns_number_gt 3951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL NT' _computing_publication_material 'SHELXTL NT' _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^)+(0.0914P)^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 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5771 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1490 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.897 _refine_ls_shift/su_mean 0.017 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 O1 O -0.27560(8) 0.95248(17) -0.12031(5) 0.0392(4) Uani 1 1 d . . . C1 C -0.25033(9) 0.8246(2) -0.12136(6) 0.0262(4) Uani 1 1 d . . . O2A O -0.18860(7) 0.95600(17) -0.02301(5) 0.0378(4) Uani 1 1 d . . . O2B O -0.11174(7) 0.86614(18) -0.06848(5) 0.0397(4) Uani 1 1 d . . . C2A C -0.17109(9) 0.8713(2) -0.05253(7) 0.0260(4) Uani 1 1 d . . . C2 C -0.21617(9) 0.7605(2) -0.07822(6) 0.0240(4) Uani 1 1 d . . . C2B C -0.06399(12) 0.9621(4) -0.04425(10) 0.0619(8) Uani 1 1 d . . . H2BA H -0.0205 0.9396 -0.0553 0.093 Uiso 1 1 calc R . . H2BB H -0.0645 0.9398 -0.0113 0.093 Uiso 1 1 calc R . . H2BC H -0.0745 1.0721 -0.0496 0.093 Uiso 1 1 calc R . . O3B O -0.19906(6) 0.39807(15) -0.01903(4) 0.0258(3) Uani 1 1 d . . . O3A O -0.15366(7) 0.62720(16) 0.00188(5) 0.0356(4) Uani 1 1 d . . . C3 C -0.22737(9) 0.6174(2) -0.06266(6) 0.0233(4) Uani 1 1 d . . . C3A C -0.18938(9) 0.5496(2) -0.02248(6) 0.0250(4) Uani 1 1 d . . . C3B C -0.16187(11) 0.3244(3) 0.01838(7) 0.0364(5) Uani 1 1 d . . . H3BA H -0.1716 0.2126 0.0186 0.055 Uiso 1 1 calc R . . H3BB H -0.1738 0.3708 0.0476 0.055 Uiso 1 1 calc R . . H3BC H -0.1151 0.3399 0.0142 0.055 Uiso 1 1 calc R . . C11 C -0.24744(9) 0.7278(2) -0.16339(6) 0.0251(4) Uani 1 1 d . . . C12 C -0.18938(10) 0.6525(2) -0.17114(7) 0.0315(5) Uani 1 1 d . . . H12A H -0.1541 0.6592 -0.1490 0.038 Uiso 1 1 calc R . . C13 C -0.18214(10) 0.5660(3) -0.21152(7) 0.0373(5) Uani 1 1 d . . . H13A H -0.1418 0.5158 -0.2168 0.045 Uiso 1 1 calc R . . C14 C -0.23219(11) 0.5542(3) -0.24273(7) 0.0386(5) Uani 1 1 d . . . H14A H -0.2263 0.4971 -0.2702 0.046 Uiso 1 1 calc R . . C15 C -0.29341(10) 0.6248(2) -0.23574(7) 0.0319(5) Uani 1 1 d . . . C16 C -0.34685(12) 0.6095(3) -0.26828(8) 0.0417(6) Uani 1 1 d . . . H16A H -0.3415 0.5504 -0.2954 0.050 Uiso 1 1 calc R . . C17 C -0.40509(11) 0.6777(3) -0.26120(8) 0.0421(6) Uani 1 1 d . . . H17A H -0.4400 0.6679 -0.2836 0.051 Uiso 1 1 calc R . . C18 C -0.41403(10) 0.7628(3) -0.22096(7) 0.0354(5) Uani 1 1 d . . . H18A H -0.4554 0.8084 -0.2159 0.043 Uiso 1 1 calc R . . C19 C -0.36412(9) 0.7808(2) -0.18902(7) 0.0284(4) Uani 1 1 d . . . H19A H -0.3711 0.8389 -0.1619 0.034 Uiso 1 1 calc R . . C20 C -0.30188(9) 0.7143(2) -0.19551(6) 0.0254(4) Uani 1 1 d . . . N21 N -0.27883(7) 0.52700(18) -0.08454(5) 0.0227(3) Uani 1 1 d . . . C22 C -0.26585(9) 0.3986(2) -0.11020(6) 0.0256(4) Uani 1 1 d . . . H22A H -0.2225 0.3593 -0.1101 0.031 Uiso 1 1 calc R . . C23 C -0.31330(9) 0.3264(2) -0.13566(7) 0.0271(4) Uani 1 1 d . . . H23A H -0.3027 0.2373 -0.1532 0.033 Uiso 1 1 calc R . . C24 C -0.37923(9) 0.3813(2) -0.13678(6) 0.0250(4) Uani 1 1 d . . . N24A N -0.42597(8) 0.31571(19) -0.16340(6) 0.0302(4) Uani 1 1 d . . . C24C C -0.49343(10) 0.3718(3) -0.16572(9) 0.0432(6) Uani 1 1 d . . . H24A H -0.4956 0.4735 -0.1506 0.065 Uiso 1 1 calc R . . H24B H -0.5214 0.2975 -0.1502 0.065 Uiso 1 1 calc R . . H24C H -0.5086 0.3821 -0.1979 0.065 Uiso 1 1 calc R . . C24B C -0.41196(11) 0.1881(3) -0.19444(8) 0.0466(6) Uani 1 1 d . . . H24D H -0.3799 0.1178 -0.1795 0.070 Uiso 1 1 calc R . . H24E H -0.3943 0.2300 -0.2226 0.070 Uiso 1 1 calc R . . H24F H -0.4523 0.1305 -0.2021 0.070 Uiso 1 1 calc R . . C25 C -0.39117(9) 0.5111(2) -0.10786(6) 0.0254(4) Uani 1 1 d . . . H25A H -0.4344 0.5501 -0.1059 0.031 Uiso 1 1 calc R . . C26 C -0.34176(9) 0.5792(2) -0.08328(6) 0.0247(4) Uani 1 1 d . . . H26A H -0.3510 0.6663 -0.0645 0.030 Uiso 1 1 calc R . . S100 S 0.04865(2) 0.62116(6) 0.122216(18) 0.03213(16) Uani 1 1 d . . . C100 C -0.00866(11) 0.5500(3) 0.07815(8) 0.0454(6) Uani 1 1 d . . . F101 F 0.00260(9) 0.4037(2) 0.06674(6) 0.0822(6) Uani 1 1 d . . . O101 O 0.02718(8) 0.77764(19) 0.12844(6) 0.0509(4) Uani 1 1 d . . . O102 O 0.11035(7) 0.6047(2) 0.10169(6) 0.0515(5) Uani 1 1 d . . . F102 F -0.00694(8) 0.6343(2) 0.04012(5) 0.0727(5) Uani 1 1 d . . . F103 F -0.06992(7) 0.5560(2) 0.09199(5) 0.0681(5) Uani 1 1 d . . . O103 O 0.03869(7) 0.5201(2) 0.16044(5) 0.0477(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0515(9) 0.0262(8) 0.0390(8) -0.0036(7) -0.0093(7) 0.0101(7) C1 0.0273(10) 0.0235(10) 0.0279(10) 0.0023(8) 0.0005(8) -0.0016(8) O2A 0.0389(9) 0.0345(9) 0.0401(9) -0.0127(7) 0.0030(7) -0.0042(7) O2B 0.0309(8) 0.0515(10) 0.0370(8) -0.0107(7) 0.0068(7) -0.0164(7) C2A 0.0283(10) 0.0248(11) 0.0247(10) 0.0005(8) 0.0009(8) -0.0029(8) C2 0.0235(9) 0.0234(10) 0.0252(9) -0.0022(8) 0.0019(8) -0.0007(8) C2B 0.0406(14) 0.085(2) 0.0602(16) -0.0178(16) 0.0045(12) -0.0351(14) O3B 0.0271(7) 0.0243(7) 0.0254(7) 0.0015(6) -0.0036(6) -0.0012(5) O3A 0.0386(8) 0.0309(8) 0.0359(8) 0.0020(7) -0.0144(7) -0.0077(6) C3 0.0227(9) 0.0239(10) 0.0232(9) -0.0040(8) 0.0001(7) -0.0014(7) C3A 0.0243(9) 0.0264(11) 0.0244(10) 0.0008(8) -0.0003(8) -0.0016(8) C3B 0.0430(12) 0.0301(11) 0.0351(12) 0.0073(10) -0.0106(10) 0.0008(10) C11 0.0290(10) 0.0235(10) 0.0228(9) 0.0033(8) 0.0033(8) 0.0007(8) C12 0.0304(10) 0.0342(12) 0.0300(11) 0.0054(9) 0.0017(8) 0.0066(9) C13 0.0366(12) 0.0426(13) 0.0331(11) 0.0020(10) 0.0078(10) 0.0151(10) C14 0.0486(13) 0.0374(13) 0.0303(11) -0.0051(10) 0.0072(10) 0.0095(10) C15 0.0389(11) 0.0296(12) 0.0273(10) -0.0011(9) 0.0011(9) 0.0030(9) C16 0.0545(14) 0.0397(14) 0.0304(11) -0.0089(10) -0.0045(10) 0.0032(11) C17 0.0419(13) 0.0434(14) 0.0397(13) -0.0022(11) -0.0153(10) -0.0026(11) C18 0.0297(11) 0.0374(12) 0.0388(12) 0.0038(10) -0.0031(9) 0.0022(9) C19 0.0311(10) 0.0271(11) 0.0270(10) 0.0011(8) 0.0011(8) 0.0017(8) C20 0.0312(10) 0.0220(10) 0.0229(9) 0.0034(8) 0.0003(8) -0.0011(8) N21 0.0218(7) 0.0232(9) 0.0229(8) -0.0006(7) -0.0023(6) -0.0002(6) C22 0.0257(9) 0.0232(10) 0.0278(10) -0.0007(8) -0.0005(8) 0.0010(8) C23 0.0299(10) 0.0225(10) 0.0290(10) -0.0039(8) 0.0011(8) 0.0017(8) C24 0.0261(9) 0.0243(10) 0.0243(9) 0.0024(8) -0.0019(8) -0.0053(8) N24A 0.0258(8) 0.0294(9) 0.0348(9) -0.0078(8) -0.0043(7) -0.0021(7) C24C 0.0269(10) 0.0453(14) 0.0559(15) -0.0142(11) -0.0159(10) 0.0011(10) C24B 0.0360(12) 0.0473(15) 0.0557(15) -0.0247(12) -0.0069(11) -0.0026(11) C25 0.0221(9) 0.0267(10) 0.0274(10) 0.0004(8) 0.0003(8) 0.0004(8) C26 0.0261(9) 0.0243(10) 0.0239(9) 0.0001(8) 0.0031(8) 0.0024(8) S100 0.0241(3) 0.0383(3) 0.0337(3) -0.0020(2) -0.0027(2) 0.0046(2) C100 0.0375(12) 0.0620(17) 0.0366(13) -0.0102(12) 0.0008(10) 0.0041(11) F101 0.0832(12) 0.0727(12) 0.0894(13) -0.0442(11) -0.0110(10) 0.0012(9) O101 0.0583(11) 0.0397(10) 0.0536(10) -0.0070(8) -0.0113(8) 0.0134(8) O102 0.0249(8) 0.0776(13) 0.0521(10) 0.0001(9) 0.0037(7) 0.0048(8) F102 0.0632(10) 0.1190(15) 0.0347(8) 0.0046(9) -0.0106(7) -0.0041(9) F103 0.0302(7) 0.1239(14) 0.0497(9) -0.0186(9) -0.0029(7) -0.0078(8) O103 0.0446(9) 0.0582(11) 0.0394(9) 0.0104(8) -0.0057(7) -0.0019(8) _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 O1 C1 1.214(2) . ? C1 C11 1.484(3) . ? C1 C2 1.515(3) . ? O2A C2A 1.193(2) . ? O2B C2A 1.320(2) . ? O2B C2B 1.439(3) . ? C2A C2 1.502(3) . ? C2 C3 1.333(3) . ? O3B C3A 1.320(2) . ? O3B C3B 1.447(2) . ? O3A C3A 1.199(2) . ? C3 N21 1.435(2) . ? C3 C3A 1.495(3) . ? C11 C12 1.380(3) . ? C11 C20 1.429(3) . ? C12 C13 1.404(3) . ? C13 C14 1.344(3) . ? C14 C15 1.415(3) . ? C15 C20 1.418(3) . ? C15 C16 1.422(3) . ? C16 C17 1.352(3) . ? C17 C18 1.400(3) . ? C18 C19 1.361(3) . ? C19 C20 1.416(3) . ? N21 C22 1.364(2) . ? N21 C26 1.366(2) . ? C22 C23 1.347(3) . ? C23 C24 1.429(3) . ? C24 N24A 1.330(2) . ? C24 C25 1.424(3) . ? N24A C24B 1.457(3) . ? N24A C24C 1.461(3) . ? C25 C26 1.347(3) . ? S100 O101 1.4272(16) . ? S100 O102 1.4279(14) . ? S100 O103 1.4333(16) . ? S100 C100 1.807(3) . ? C100 F101 1.322(3) . ? C100 F102 1.325(3) . ? C100 F103 1.335(3) . ? 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 C1 C11 124.02(18) . . ? O1 C1 C2 119.30(17) . . ? C11 C1 C2 116.60(16) . . ? C2A O2B C2B 115.09(17) . . ? O2A C2A O2B 125.71(18) . . ? O2A C2A C2 123.21(17) . . ? O2B C2A C2 111.01(15) . . ? C3 C2 C2A 121.67(17) . . ? C3 C2 C1 122.48(17) . . ? C2A C2 C1 115.79(16) . . ? C3A O3B C3B 114.33(15) . . ? C2 C3 N21 118.76(17) . . ? C2 C3 C3A 122.28(17) . . ? N21 C3 C3A 118.95(16) . . ? O3A C3A O3B 126.30(18) . . ? O3A C3A C3 122.03(18) . . ? O3B C3A C3 111.63(16) . . ? C12 C11 C20 120.53(18) . . ? C12 C11 C1 117.57(18) . . ? C20 C11 C1 121.89(16) . . ? C11 C12 C13 120.5(2) . . ? C14 C13 C12 120.10(19) . . ? C13 C14 C15 121.6(2) . . ? C14 C15 C20 119.4(2) . . ? C14 C15 C16 121.68(19) . . ? C20 C15 C16 118.87(19) . . ? C17 C16 C15 121.1(2) . . ? C16 C17 C18 120.1(2) . . ? C19 C18 C17 120.7(2) . . ? C18 C19 C20 121.09(19) . . ? C19 C20 C15 118.12(18) . . ? C19 C20 C11 124.11(17) . . ? C15 C20 C11 117.74(17) . . ? C22 N21 C26 119.07(16) . . ? C22 N21 C3 121.57(15) . . ? C26 N21 C3 119.06(15) . . ? C23 C22 N21 121.36(17) . . ? C22 C23 C24 121.25(18) . . ? N24A C24 C25 122.58(17) . . ? N24A C24 C23 121.91(18) . . ? C25 C24 C23 115.51(17) . . ? C24 N24A C24B 121.62(17) . . ? C24 N24A C24C 122.81(17) . . ? C24B N24A C24C 115.47(17) . . ? C26 C25 C24 120.64(17) . . ? C25 C26 N21 122.06(18) . . ? O101 S100 O102 115.42(11) . . ? O101 S100 O103 114.60(10) . . ? O102 S100 O103 115.06(10) . . ? O101 S100 C100 102.36(11) . . ? O102 S100 C100 103.18(10) . . ? O103 S100 C100 103.74(11) . . ? F101 C100 F102 107.30(19) . . ? F101 C100 F103 106.8(2) . . ? F102 C100 F103 106.9(2) . . ? F101 C100 S100 112.62(18) . . ? F102 C100 S100 111.69(18) . . ? F103 C100 S100 111.22(15) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.367 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.113