data_rc207 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 N O5 S' _chemical_formula_weight 415.49 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 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 9.905(2) _cell_length_b 11.443(2) _cell_length_c 18.969(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2150.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5571 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 22.5 _exptl_crystal_description Block-shaped _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9523 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-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_% 1 _diffrn_reflns_number 15932 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3773 _reflns_number_gt 3000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0500P)^2^+0.0800P] 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_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(8) _refine_ls_number_reflns 3773 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.009 _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 0.36442(8) 0.47137(6) 0.33731(3) 0.0722(2) Uani 1 1 d . . . O1 O 0.25926(18) 0.5249(2) 0.29807(10) 0.0958(7) Uani 1 1 d . . . O2 O 0.3517(3) 0.35466(17) 0.36271(10) 0.1021(8) Uani 1 1 d . . . O3 O 0.5606(2) 0.68929(18) 0.62220(10) 0.0883(6) Uani 1 1 d . . . O4 O 0.3907(2) 0.79767(15) 0.58326(8) 0.0720(5) Uani 1 1 d . . . O5 O 0.37724(16) 0.51148(12) 0.52766(8) 0.0582(4) Uani 1 1 d . . . N1 N 0.3895(2) 0.55347(17) 0.40703(9) 0.0596(5) Uani 1 1 d . . . C1 C 0.5269(3) 0.5626(2) 0.23655(13) 0.0670(7) Uani 1 1 d . . . H1 H 0.4611 0.6200 0.2317 0.080 Uiso 1 1 calc R . . C2 C 0.6392(3) 0.5638(3) 0.19430(14) 0.0821(8) Uani 1 1 d . . . H2 H 0.6492 0.6219 0.1604 0.098 Uiso 1 1 calc R . . C3 C 0.7351(3) 0.4813(3) 0.20157(18) 0.0904(9) Uani 1 1 d . . . H3 H 0.8107 0.4827 0.1725 0.108 Uiso 1 1 calc R . . C4 C 0.7224(4) 0.3955(3) 0.2513(2) 0.0926(10) Uani 1 1 d . . . H4 H 0.7894 0.3390 0.2560 0.111 Uiso 1 1 calc R . . C5 C 0.6105(3) 0.3925(2) 0.29454(15) 0.0788(8) Uani 1 1 d . . . H5 H 0.6015 0.3350 0.3289 0.095 Uiso 1 1 calc R . . C6 C 0.5122(2) 0.4764(2) 0.28585(12) 0.0568(6) Uani 1 1 d . . . C7 C 0.3727(3) 0.6760(2) 0.40246(12) 0.0595(6) Uani 1 1 d . . . H7 H 0.3164 0.7060 0.3677 0.071 Uiso 1 1 calc R . . C8 C 0.4334(3) 0.7487(2) 0.44528(12) 0.0604(6) Uani 1 1 d . . . H8 H 0.4108 0.8274 0.4424 0.072 Uiso 1 1 calc R . . C9 C 0.5352(2) 0.7136(2) 0.49785(12) 0.0560(6) Uani 1 1 d . . . H9 H 0.6145 0.7630 0.4895 0.067 Uiso 1 1 calc R . . C10 C 0.5804(2) 0.5882(2) 0.48445(13) 0.0597(6) Uani 1 1 d . . . H10A H 0.6428 0.5868 0.4451 0.072 Uiso 1 1 calc R . . H10B H 0.6276 0.5591 0.5257 0.072 Uiso 1 1 calc R . . C11 C 0.4632(2) 0.5099(2) 0.46861(12) 0.0557(6) Uani 1 1 d . . . H11 H 0.4950 0.4301 0.4598 0.067 Uiso 1 1 calc R . . C12 C 0.4976(3) 0.7299(2) 0.57475(14) 0.0617(7) Uani 1 1 d . . . C13 C 0.3513(4) 0.8175(3) 0.65689(13) 0.0851(9) Uani 1 1 d . . . H13A H 0.3010 0.8900 0.6604 0.102 Uiso 1 1 calc R . . H13B H 0.4316 0.8248 0.6858 0.102 Uiso 1 1 calc R . . C14 C 0.2680(4) 0.7206(3) 0.68321(16) 0.0996(10) Uani 1 1 d . . . H14A H 0.1930 0.7085 0.6519 0.149 Uiso 1 1 calc R . . H14B H 0.2349 0.7393 0.7294 0.149 Uiso 1 1 calc R . . H14C H 0.3214 0.6507 0.6854 0.149 Uiso 1 1 calc R . . C15 C 0.2845(2) 0.4146(2) 0.53102(14) 0.0591(6) Uani 1 1 d . . . H15 H 0.2430 0.4030 0.4847 0.071 Uiso 1 1 calc R . . C16 C 0.1774(3) 0.4479(3) 0.58343(15) 0.0786(8) Uani 1 1 d . . . H16A H 0.2175 0.4567 0.6292 0.118 Uiso 1 1 calc R . . H16B H 0.1098 0.3879 0.5851 0.118 Uiso 1 1 calc R . . H16C H 0.1366 0.5204 0.5694 0.118 Uiso 1 1 calc R . . C17 C 0.3569(2) 0.3048(2) 0.55266(12) 0.0546(6) Uani 1 1 d . . . C18 C 0.3285(3) 0.1995(2) 0.52133(16) 0.0720(7) Uani 1 1 d . . . H18 H 0.2655 0.1961 0.4850 0.086 Uiso 1 1 calc R . . C19 C 0.3931(3) 0.0976(3) 0.5434(2) 0.0910(10) Uani 1 1 d . . . H19 H 0.3724 0.0267 0.5220 0.109 Uiso 1 1 calc R . . C20 C 0.4851(3) 0.1014(3) 0.5954(2) 0.0979(11) Uani 1 1 d . . . H20 H 0.5285 0.0333 0.6098 0.117 Uiso 1 1 calc R . . C21 C 0.5146(3) 0.2043(3) 0.6269(2) 0.0958(10) Uani 1 1 d . . . H21 H 0.5782 0.2068 0.6629 0.115 Uiso 1 1 calc R . . C22 C 0.4509(3) 0.3059(3) 0.60586(16) 0.0803(8) Uani 1 1 d . . . H22 H 0.4720 0.3760 0.6281 0.096 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 0.0774(4) 0.0811(5) 0.0580(4) -0.0143(3) 0.0090(4) -0.0228(4) O1 0.0643(10) 0.1506(19) 0.0724(12) -0.0251(13) -0.0102(10) -0.0087(13) O2 0.148(2) 0.0767(12) 0.0819(13) -0.0180(11) 0.0295(14) -0.0515(14) O3 0.0892(13) 0.1076(15) 0.0682(12) 0.0052(12) -0.0217(11) 0.0134(12) O4 0.0975(13) 0.0605(10) 0.0579(10) 0.0019(8) 0.0017(10) 0.0182(10) O5 0.0737(9) 0.0509(9) 0.0499(8) -0.0005(7) 0.0146(8) -0.0061(8) N1 0.0737(12) 0.0586(12) 0.0464(11) -0.0014(9) 0.0076(10) -0.0056(10) C1 0.0759(17) 0.0709(17) 0.0541(15) 0.0012(13) 0.0041(13) 0.0041(14) C2 0.096(2) 0.0865(19) 0.0641(17) -0.0014(15) 0.0165(17) -0.010(2) C3 0.084(2) 0.104(3) 0.083(2) -0.032(2) 0.0198(17) -0.006(2) C4 0.084(2) 0.090(2) 0.104(3) -0.030(2) -0.004(2) 0.0269(19) C5 0.103(2) 0.0653(16) 0.0687(17) -0.0071(14) -0.0075(18) 0.0065(17) C6 0.0696(15) 0.0545(14) 0.0463(13) -0.0130(11) -0.0049(11) -0.0045(13) C7 0.0638(15) 0.0680(16) 0.0468(13) 0.0059(12) 0.0024(12) 0.0092(13) C8 0.0737(16) 0.0516(14) 0.0558(15) 0.0038(12) 0.0089(13) 0.0053(13) C9 0.0568(14) 0.0521(14) 0.0591(15) 0.0043(12) 0.0027(12) -0.0059(11) C10 0.0515(14) 0.0660(16) 0.0616(15) 0.0048(12) 0.0072(11) 0.0087(12) C11 0.0687(14) 0.0443(13) 0.0541(13) 0.0015(11) 0.0112(12) 0.0048(11) C12 0.0666(16) 0.0530(15) 0.0655(17) 0.0025(12) -0.0068(14) -0.0048(13) C13 0.121(2) 0.0775(18) 0.0566(16) -0.0054(14) 0.0015(17) 0.0247(18) C14 0.140(3) 0.091(2) 0.0675(19) 0.0000(17) 0.018(2) 0.004(2) C15 0.0632(14) 0.0566(15) 0.0574(14) 0.0063(12) 0.0035(12) -0.0069(12) C16 0.0704(16) 0.0792(18) 0.086(2) 0.0085(16) 0.0200(14) -0.0007(14) C17 0.0547(13) 0.0525(13) 0.0568(14) 0.0051(11) 0.0084(12) -0.0087(12) C18 0.0690(17) 0.0614(16) 0.0856(19) -0.0017(15) 0.0061(14) -0.0062(14) C19 0.081(2) 0.0542(17) 0.138(3) -0.0025(18) 0.022(2) -0.0091(16) C20 0.0670(19) 0.072(2) 0.155(3) 0.030(2) 0.008(2) 0.0034(16) C21 0.079(2) 0.091(2) 0.118(3) 0.026(2) -0.021(2) 0.0031(19) C22 0.0837(19) 0.0684(17) 0.089(2) 0.0061(16) -0.0112(17) -0.0055(15) _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 1.419(2) . ? S1 O2 1.425(2) . ? S1 N1 1.6412(19) . ? S1 C6 1.760(2) . ? O3 C12 1.190(3) . ? O4 C12 1.322(3) . ? O4 C13 1.468(3) . ? O5 C11 1.407(3) . ? O5 C15 1.441(3) . ? N1 C7 1.414(3) . ? N1 C11 1.465(3) . ? C1 C2 1.372(4) . ? C1 C6 1.367(3) . ? C2 C3 1.346(4) . ? C3 C4 1.368(4) . ? C4 C5 1.380(4) . ? C5 C6 1.377(4) . ? C7 C8 1.309(3) . ? C8 C9 1.474(3) . ? C9 C12 1.517(3) . ? C9 C10 1.524(3) . ? C10 C11 1.497(3) . ? C13 C14 1.469(4) . ? C15 C16 1.503(3) . ? C15 C17 1.504(3) . ? C17 C18 1.373(3) . ? C17 C22 1.373(4) . ? C18 C19 1.395(4) . ? C19 C20 1.344(5) . ? C20 C21 1.352(5) . ? C21 C22 1.380(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 O2 121.11(14) . . ? O1 S1 N1 106.65(12) . . ? O2 S1 N1 106.10(11) . . ? O1 S1 C6 107.78(11) . . ? O2 S1 C6 106.95(13) . . ? N1 S1 C6 107.62(11) . . ? C12 O4 C13 114.8(2) . . ? C11 O5 C15 114.27(17) . . ? C7 N1 C11 116.41(19) . . ? C7 N1 S1 120.02(16) . . ? C11 N1 S1 121.54(16) . . ? C2 C1 C6 119.6(3) . . ? C3 C2 C1 120.4(3) . . ? C2 C3 C4 120.6(3) . . ? C3 C4 C5 120.1(3) . . ? C6 C5 C4 118.7(3) . . ? C1 C6 C5 120.6(2) . . ? C1 C6 S1 119.4(2) . . ? C5 C6 S1 119.9(2) . . ? C8 C7 N1 122.5(2) . . ? C7 C8 C9 124.1(2) . . ? C8 C9 C12 116.6(2) . . ? C8 C9 C10 110.1(2) . . ? C12 C9 C10 110.4(2) . . ? C11 C10 C9 111.68(19) . . ? O5 C11 N1 109.21(17) . . ? O5 C11 C10 107.56(18) . . ? N1 C11 C10 110.05(19) . . ? O3 C12 O4 123.8(3) . . ? O3 C12 C9 123.4(2) . . ? O4 C12 C9 112.7(2) . . ? O4 C13 C14 110.9(2) . . ? O5 C15 C16 106.50(19) . . ? O5 C15 C17 110.53(19) . . ? C16 C15 C17 111.6(2) . . ? C18 C17 C22 117.7(2) . . ? C18 C17 C15 121.2(2) . . ? C22 C17 C15 121.1(2) . . ? C17 C18 C19 120.7(3) . . ? C20 C19 C18 120.3(3) . . ? C19 C20 C21 119.9(3) . . ? C20 C21 C22 120.5(3) . . ? C17 C22 C21 120.9(3) . . ? 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 N1 C7 -33.8(2) . . . . ? O2 S1 N1 C7 -164.2(2) . . . . ? C6 S1 N1 C7 81.6(2) . . . . ? O1 S1 N1 C11 163.02(17) . . . . ? O2 S1 N1 C11 32.7(2) . . . . ? C6 S1 N1 C11 -81.55(19) . . . . ? C6 C1 C2 C3 -0.5(4) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? C2 C1 C6 S1 -177.2(2) . . . . ? C4 C5 C6 C1 -1.6(4) . . . . ? C4 C5 C6 S1 177.1(2) . . . . ? O1 S1 C6 C1 26.5(2) . . . . ? O2 S1 C6 C1 158.2(2) . . . . ? N1 S1 C6 C1 -88.2(2) . . . . ? O1 S1 C6 C5 -152.2(2) . . . . ? O2 S1 C6 C5 -20.5(2) . . . . ? N1 S1 C6 C5 93.1(2) . . . . ? C11 N1 C7 C8 8.5(3) . . . . ? S1 N1 C7 C8 -155.5(2) . . . . ? N1 C7 C8 C9 6.3(4) . . . . ? C7 C8 C9 C12 -114.8(3) . . . . ? C7 C8 C9 C10 12.0(3) . . . . ? C8 C9 C10 C11 -43.7(3) . . . . ? C12 C9 C10 C11 86.5(3) . . . . ? C15 O5 C11 N1 79.6(2) . . . . ? C15 O5 C11 C10 -161.02(18) . . . . ? C7 N1 C11 O5 77.6(2) . . . . ? S1 N1 C11 O5 -118.61(18) . . . . ? C7 N1 C11 C10 -40.2(3) . . . . ? S1 N1 C11 C10 123.53(18) . . . . ? C9 C10 C11 O5 -60.7(3) . . . . ? C9 C10 C11 N1 58.2(2) . . . . ? C13 O4 C12 O3 -1.6(4) . . . . ? C13 O4 C12 C9 -179.2(2) . . . . ? C8 C9 C12 O3 168.1(2) . . . . ? C10 C9 C12 O3 41.4(3) . . . . ? C8 C9 C12 O4 -14.4(3) . . . . ? C10 C9 C12 O4 -141.1(2) . . . . ? C12 O4 C13 C14 -83.2(3) . . . . ? C11 O5 C15 C16 -163.98(19) . . . . ? C11 O5 C15 C17 74.6(2) . . . . ? O5 C15 C17 C18 -139.1(2) . . . . ? C16 C15 C17 C18 102.6(3) . . . . ? O5 C15 C17 C22 42.9(3) . . . . ? C16 C15 C17 C22 -75.5(3) . . . . ? C22 C17 C18 C19 0.2(4) . . . . ? C15 C17 C18 C19 -177.9(2) . . . . ? C17 C18 C19 C20 -0.5(4) . . . . ? C18 C19 C20 C21 0.4(5) . . . . ? C19 C20 C21 C22 -0.1(5) . . . . ? C18 C17 C22 C21 0.1(4) . . . . ? C15 C17 C22 C21 178.3(3) . . . . ? C20 C21 C22 C17 -0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.135 _refine_diff_density_min -0.117 _refine_diff_density_rms 0.027