data_baran181 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O6 S' _chemical_formula_weight 445.52 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' '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 12.6275(4) _cell_length_b 8.5892(3) _cell_length_c 20.4658(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.32 _cell_angle_gamma 90.00 _cell_volume 2190.39(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7528 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.39 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9253 _exptl_absorpt_correction_T_max 0.9778 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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_reflns_number 13669 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.39 _reflns_number_total 4017 _reflns_number_gt 3608 _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, 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^)+(0.0340P)^2^+1.3000P] 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 4017 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.006 _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 S1 S 0.73777(3) 0.46589(4) 0.864466(18) 0.01880(11) Uani 1 1 d . . . O1 O 0.11503(8) 0.63199(13) 0.90910(5) 0.0214(2) Uani 1 1 d . . . O2 O 0.41573(8) 0.25896(12) 0.75176(5) 0.0191(2) Uani 1 1 d . . . O3 O 0.20453(9) 0.31929(13) 0.52153(5) 0.0241(3) Uani 1 1 d . . . O4 O 0.12858(9) 0.53056(13) 0.55910(6) 0.0280(3) Uani 1 1 d . . . O5 O 0.05305(8) 0.38576(13) 0.83400(5) 0.0216(2) Uani 1 1 d . . . O6 O 0.24975(9) 0.84513(13) 0.87240(5) 0.0231(3) Uani 1 1 d . . . N1 N 0.51003(10) 0.46696(15) 0.79925(6) 0.0175(3) Uani 1 1 d . . . H1 H 0.5405 0.5531 0.7915 0.021 Uiso 1 1 calc R . . C1 C 0.85286(12) 0.4246(2) 0.92639(8) 0.0242(4) Uani 1 1 d . . . H1A H 0.8503 0.4880 0.9647 0.036 Uiso 1 1 calc R . . H1B H 0.9173 0.4471 0.9089 0.036 Uiso 1 1 calc R . . H1C H 0.8523 0.3167 0.9385 0.036 Uiso 1 1 calc R . . C2 C 0.62945(12) 0.40344(17) 0.90299(7) 0.0178(3) Uani 1 1 d . . . C3 C 0.52591(12) 0.40927(17) 0.86581(7) 0.0176(3) Uani 1 1 d . . . C4 C 0.44946(11) 0.39277(17) 0.74775(7) 0.0161(3) Uani 1 1 d . . . C5 C 0.42105(11) 0.48874(17) 0.68584(7) 0.0159(3) Uani 1 1 d . . . H5 H 0.4704 0.5752 0.6821 0.019 Uiso 1 1 calc R . . C6 C 0.29842(11) 0.53736(17) 0.67681(7) 0.0149(3) Uani 1 1 d . . . H6 H 0.2892 0.6337 0.6509 0.018 Uiso 1 1 calc R . . C7 C 0.24648(11) 0.55866(17) 0.73740(7) 0.0156(3) Uani 1 1 d . . . C8 C 0.27375(12) 0.69162(17) 0.77549(7) 0.0169(3) Uani 1 1 d . . . H8 H 0.3218 0.7633 0.7628 0.020 Uiso 1 1 calc R . . C9 C 0.22940(12) 0.71729(18) 0.83234(7) 0.0179(3) Uani 1 1 d . . . C10 C 0.15670(12) 0.61047(18) 0.85146(7) 0.0175(3) Uani 1 1 d . . . C11 C 0.03113(13) 0.7454(2) 0.90327(8) 0.0271(4) Uani 1 1 d . . . H11A H 0.0555 0.8405 0.8860 0.041 Uiso 1 1 calc R . . H11B H 0.0120 0.7646 0.9461 0.041 Uiso 1 1 calc R . . H11C H -0.0304 0.7074 0.8738 0.041 Uiso 1 1 calc R . . C12 C 0.39278(12) 0.38962(18) 0.62194(7) 0.0174(3) Uani 1 1 d . . . H12A H 0.4095 0.4404 0.5825 0.021 Uiso 1 1 calc R . . H12B H 0.4219 0.2849 0.6261 0.021 Uiso 1 1 calc R . . C13 C 0.27260(11) 0.39901(17) 0.62904(7) 0.0160(3) Uani 1 1 d . . . H13 H 0.2518 0.3077 0.6527 0.019 Uiso 1 1 calc R . . C14 C 0.19339(12) 0.42685(18) 0.56733(7) 0.0179(3) Uani 1 1 d . . . C15 C 0.13541(14) 0.3369(2) 0.45818(8) 0.0308(4) Uani 1 1 d . . . H15A H 0.0626 0.3508 0.4651 0.046 Uiso 1 1 calc R . . H15B H 0.1401 0.2453 0.4319 0.046 Uiso 1 1 calc R . . H15C H 0.1577 0.4260 0.4356 0.046 Uiso 1 1 calc R . . C16 C 0.17381(12) 0.45215(17) 0.75581(7) 0.0168(3) Uani 1 1 d . . . H16 H 0.1558 0.3633 0.7305 0.020 Uiso 1 1 calc R . . C17 C 0.12805(12) 0.47919(17) 0.81245(7) 0.0167(3) Uani 1 1 d . . . C18 C 0.02129(14) 0.2475(2) 0.79746(8) 0.0286(4) Uani 1 1 d . . . H18A H -0.0112 0.2747 0.7532 0.043 Uiso 1 1 calc R . . H18B H -0.0294 0.1913 0.8187 0.043 Uiso 1 1 calc R . . H18C H 0.0831 0.1835 0.7959 0.043 Uiso 1 1 calc R . . C19 C 0.31854(14) 0.9615(2) 0.85206(9) 0.0298(4) Uani 1 1 d . . . H19A H 0.3870 0.9162 0.8489 0.045 Uiso 1 1 calc R . . H19B H 0.3279 1.0443 0.8840 0.045 Uiso 1 1 calc R . . H19C H 0.2869 1.0021 0.8097 0.045 Uiso 1 1 calc R . . C20 C 0.43753(12) 0.36217(18) 0.89344(8) 0.0202(3) Uani 1 1 d . . . H20 H 0.3691 0.3686 0.8687 0.024 Uiso 1 1 calc R . . C21 C 0.45104(13) 0.30551(19) 0.95778(8) 0.0244(4) Uani 1 1 d . . . H21 H 0.3920 0.2733 0.9762 0.029 Uiso 1 1 calc R . . C22 C 0.55356(13) 0.29739(19) 0.99445(8) 0.0241(4) Uani 1 1 d . . . H22 H 0.5629 0.2584 1.0374 0.029 Uiso 1 1 calc R . . C23 C 0.64203(13) 0.34662(18) 0.96787(8) 0.0208(3) Uani 1 1 d . . . H23 H 0.7101 0.3419 0.9933 0.025 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 0.0193(2) 0.0197(2) 0.0176(2) 0.00109(14) 0.00343(15) -0.00143(15) O1 0.0210(6) 0.0297(6) 0.0148(5) -0.0011(4) 0.0067(4) 0.0021(5) O2 0.0207(5) 0.0160(5) 0.0200(5) -0.0005(4) 0.0013(4) 0.0008(4) O3 0.0253(6) 0.0305(6) 0.0153(5) -0.0055(5) -0.0004(4) 0.0024(5) O4 0.0246(6) 0.0265(6) 0.0296(7) -0.0022(5) -0.0056(5) 0.0058(5) O5 0.0226(6) 0.0237(6) 0.0192(6) -0.0010(4) 0.0061(4) -0.0069(5) O6 0.0230(6) 0.0243(6) 0.0238(6) -0.0093(5) 0.0087(5) -0.0067(5) N1 0.0195(6) 0.0169(6) 0.0156(6) 0.0002(5) 0.0009(5) -0.0022(5) C1 0.0181(8) 0.0277(9) 0.0262(8) 0.0033(7) 0.0019(6) -0.0017(7) C2 0.0203(8) 0.0155(7) 0.0180(7) -0.0020(6) 0.0045(6) -0.0013(6) C3 0.0213(8) 0.0158(7) 0.0155(7) -0.0020(6) 0.0021(6) 0.0003(6) C4 0.0128(7) 0.0174(7) 0.0185(8) -0.0025(6) 0.0037(6) 0.0030(6) C5 0.0135(7) 0.0182(7) 0.0162(7) -0.0006(6) 0.0036(6) 0.0006(6) C6 0.0141(7) 0.0149(7) 0.0156(7) -0.0002(6) 0.0023(5) 0.0010(6) C7 0.0140(7) 0.0180(7) 0.0143(7) 0.0016(6) 0.0011(6) 0.0035(6) C8 0.0146(7) 0.0184(7) 0.0182(7) 0.0005(6) 0.0036(6) 0.0003(6) C9 0.0162(7) 0.0193(8) 0.0174(7) -0.0024(6) 0.0005(6) 0.0018(6) C10 0.0161(7) 0.0231(8) 0.0136(7) 0.0013(6) 0.0030(6) 0.0033(6) C11 0.0250(8) 0.0321(9) 0.0266(9) -0.0027(7) 0.0115(7) 0.0049(7) C12 0.0170(7) 0.0207(8) 0.0146(7) -0.0019(6) 0.0029(6) 0.0014(6) C13 0.0175(7) 0.0166(7) 0.0142(7) -0.0001(6) 0.0033(6) -0.0003(6) C14 0.0167(7) 0.0185(8) 0.0192(8) 0.0003(6) 0.0048(6) -0.0051(6) C15 0.0276(9) 0.0472(11) 0.0159(8) -0.0033(7) -0.0020(7) -0.0039(8) C16 0.0178(7) 0.0160(7) 0.0162(7) 0.0002(6) 0.0015(6) 0.0018(6) C17 0.0146(7) 0.0184(7) 0.0167(7) 0.0035(6) 0.0011(6) 0.0004(6) C18 0.0299(9) 0.0304(9) 0.0264(9) -0.0033(7) 0.0068(7) -0.0125(8) C19 0.0281(9) 0.0275(9) 0.0370(10) -0.0124(8) 0.0148(8) -0.0114(7) C20 0.0189(8) 0.0207(8) 0.0207(8) -0.0021(6) 0.0019(6) -0.0011(6) C21 0.0242(8) 0.0272(9) 0.0233(8) -0.0007(7) 0.0082(7) -0.0055(7) C22 0.0295(9) 0.0273(8) 0.0158(8) 0.0029(6) 0.0048(7) -0.0008(7) C23 0.0213(8) 0.0224(8) 0.0179(8) 0.0002(6) 0.0006(6) -0.0001(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 C2 1.7691(15) . ? S1 C1 1.8019(16) . ? O1 C10 1.3799(18) . ? O1 C11 1.4302(19) . ? O2 C4 1.2331(19) . ? O3 C14 1.3396(18) . ? O3 C15 1.4488(19) . ? O4 C14 1.2029(19) . ? O5 C17 1.3679(18) . ? O5 C18 1.4257(19) . ? O6 C9 1.3695(18) . ? O6 C19 1.4295(19) . ? N1 C4 1.3567(19) . ? N1 C3 1.4327(19) . ? N1 H1 0.8600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C23 1.400(2) . ? C2 C3 1.403(2) . ? C3 C20 1.390(2) . ? C4 C5 1.506(2) . ? C5 C12 1.553(2) . ? C5 C6 1.5855(19) . ? C5 H5 0.9800 . ? C6 C7 1.505(2) . ? C6 C13 1.540(2) . ? C6 H6 0.9800 . ? C7 C16 1.390(2) . ? C7 C8 1.394(2) . ? C8 C9 1.388(2) . ? C8 H8 0.9300 . ? C9 C10 1.398(2) . ? C10 C17 1.395(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.550(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.498(2) . ? C13 H13 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.396(2) . ? C16 H16 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.388(2) . ? C20 H20 0.9300 . ? C21 C22 1.389(2) . ? C21 H21 0.9300 . ? C22 C23 1.386(2) . ? C22 H22 0.9300 . ? C23 H23 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 C2 S1 C1 102.75(7) . . ? C10 O1 C11 113.57(12) . . ? C14 O3 C15 115.98(13) . . ? C17 O5 C18 118.04(12) . . ? C9 O6 C19 116.75(12) . . ? C4 N1 C3 123.42(13) . . ? C4 N1 H1 118.3 . . ? C3 N1 H1 118.3 . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C23 C2 C3 118.66(14) . . ? C23 C2 S1 123.47(12) . . ? C3 C2 S1 117.87(11) . . ? C20 C3 C2 120.53(14) . . ? C20 C3 N1 119.29(13) . . ? C2 C3 N1 120.17(13) . . ? O2 C4 N1 122.92(14) . . ? O2 C4 C5 121.91(13) . . ? N1 C4 C5 115.10(13) . . ? C4 C5 C12 113.55(12) . . ? C4 C5 C6 109.72(11) . . ? C12 C5 C6 87.67(10) . . ? C4 C5 H5 114.4 . . ? C12 C5 H5 114.4 . . ? C6 C5 H5 114.4 . . ? C7 C6 C13 122.77(12) . . ? C7 C6 C5 118.94(12) . . ? C13 C6 C5 88.45(10) . . ? C7 C6 H6 108.3 . . ? C13 C6 H6 108.3 . . ? C5 C6 H6 108.3 . . ? C16 C7 C8 120.10(13) . . ? C16 C7 C6 122.56(13) . . ? C8 C7 C6 117.34(13) . . ? C9 C8 C7 120.14(14) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? O6 C9 C8 124.54(14) . . ? O6 C9 C10 115.26(13) . . ? C8 C9 C10 120.19(14) . . ? O1 C10 C17 119.88(13) . . ? O1 C10 C9 120.67(13) . . ? C17 C10 C9 119.44(13) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C5 89.28(11) . . ? C13 C12 H12A 113.8 . . ? C5 C12 H12A 113.8 . . ? C13 C12 H12B 113.8 . . ? C5 C12 H12B 113.8 . . ? H12A C12 H12B 111.0 . . ? C14 C13 C6 117.12(12) . . ? C14 C13 C12 117.35(12) . . ? C6 C13 C12 89.42(11) . . ? C14 C13 H13 110.5 . . ? C6 C13 H13 110.5 . . ? C12 C13 H13 110.5 . . ? O4 C14 O3 123.97(14) . . ? O4 C14 C13 125.63(14) . . ? O3 C14 C13 110.39(13) . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 C16 C17 119.72(14) . . ? C7 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? O5 C17 C10 114.74(13) . . ? O5 C17 C16 124.86(13) . . ? C10 C17 C16 120.39(14) . . ? O5 C18 H18A 109.5 . . ? O5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O6 C19 H19A 109.5 . . ? O6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C3 120.28(14) . . ? C21 C20 H20 119.9 . . ? C3 C20 H20 119.9 . . ? C20 C21 C22 119.39(15) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 120.85(15) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C2 120.28(14) . . ? C22 C23 H23 119.9 . . ? C2 C23 H23 119.9 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.289 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.044