# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Magda Monari' _publ_contact_author_email magda.monari@unibo.it loop_ _publ_author_name 'M. Bandini' 'Magda Monari' 'G. Cera' 'P. Crispino' data_comp-2c _database_code_depnum_ccdc_archive 'CCDC 814206' #TrackingRef 'comp2c-5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O3 S' _chemical_formula_weight 382.47 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 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 16.779(4) _cell_length_b 13.615(4) _cell_length_c 16.919(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.050(5) _cell_angle_gamma 90.00 _cell_volume 3805.8(16) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.911 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details SADABS _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 'Bruker SMART Apex II CCD' _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 16998 _diffrn_reflns_av_R_equivalents 0.1056 _diffrn_reflns_av_sigmaI/netI 0.0818 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.88 _reflns_number_total 3298 _reflns_number_gt 1363 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0194P)^2^+15.3512P] 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 geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00054(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3298 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2131 _refine_ls_R_factor_gt 0.0949 _refine_ls_wR_factor_ref 0.1994 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 S S 0.07132(12) 0.7466(3) 0.00626(11) 0.1315(12) Uani 1 1 d . . . N2 N 0.1114(3) 0.8239(5) 0.0769(3) 0.103(2) Uani 1 1 d . . . C1 C 0.1485(4) 0.9831(8) 0.2169(4) 0.102(3) Uani 1 1 d . . . C13 C 0.0597(4) 0.8487(7) 0.1358(4) 0.114(3) Uani 1 1 d . . . H13A H 0.0734 0.8064 0.1823 0.136 Uiso 1 1 calc R . . H13B H 0.0036 0.8366 0.1123 0.136 Uiso 1 1 calc R . . C5 C 0.1627(6) 0.8896(10) 0.4614(5) 0.142(5) Uani 1 1 d . . . H5 H 0.1642 0.8738 0.5151 0.170 Uiso 1 1 calc R . . C2 C 0.1572(4) 0.9351(9) 0.3011(4) 0.102(3) Uani 1 1 d . . . C12 C 0.1976(4) 0.8074(8) 0.1103(4) 0.118(3) Uani 1 1 d . . . H12A H 0.2229 0.7745 0.0702 0.141 Uiso 1 1 calc R . . H12B H 0.2013 0.7638 0.1561 0.141 Uiso 1 1 calc R . . C4 C 0.1777(4) 0.8172(7) 0.4076(4) 0.117(3) Uani 1 1 d . . . H4 H 0.1885 0.7531 0.4252 0.141 Uiso 1 1 calc R . . C3 C 0.1763(4) 0.8415(8) 0.3266(4) 0.110(3) Uani 1 1 d . . . H3 H 0.1882 0.7942 0.2908 0.132 Uiso 1 1 calc R . . C7 C 0.1447(5) 1.0070(9) 0.3560(5) 0.110(3) Uani 1 1 d . . . C14 C 0.0691(4) 0.9550(7) 0.1625(4) 0.114(3) Uani 1 1 d . . . H14A H 0.0249 0.9709 0.1904 0.136 Uiso 1 1 calc R . . H14B H 0.0630 0.9959 0.1149 0.136 Uiso 1 1 calc R . . C6 C 0.1461(6) 0.9831(10) 0.4360(5) 0.136(5) Uani 1 1 d . . . H6 H 0.1356 1.0309 0.4720 0.163 Uiso 1 1 calc R . . C18 C 0.0743(6) 0.4498(10) 0.1320(6) 0.138(5) Uani 1 1 d . . . O3 O 0.1258(3) 0.7426(5) -0.0506(2) 0.147(3) Uani 1 1 d . . . O2 O -0.0101(3) 0.7775(5) -0.0206(2) 0.135(2) Uani 1 1 d . . . C19 C 0.1375(6) 0.4799(10) 0.0917(6) 0.143(5) Uani 1 1 d . . . H19 H 0.1816 0.4385 0.0920 0.172 Uiso 1 1 calc R . . C15 C 0.0715(5) 0.6302(8) 0.0524(4) 0.125(4) Uani 1 1 d . . . C20 C 0.1356(6) 0.5672(10) 0.0528(5) 0.143(5) Uani 1 1 d . . . H20 H 0.1778 0.5844 0.0264 0.172 Uiso 1 1 calc R . . C16 C 0.0065(6) 0.6036(10) 0.0901(6) 0.135(5) Uani 1 1 d . . . H16 H -0.0378 0.6450 0.0890 0.162 Uiso 1 1 calc R . . C17 C 0.0104(6) 0.5149(10) 0.1282(7) 0.144(5) Uani 1 1 d . . . H17 H -0.0326 0.4971 0.1532 0.173 Uiso 1 1 calc R . . C21 C 0.0794(6) 0.3531(9) 0.1760(7) 0.176(5) Uani 1 1 d . . . H21A H 0.0951 0.3645 0.2325 0.264 Uiso 1 1 calc R . . H21B H 0.1188 0.3119 0.1575 0.264 Uiso 1 1 calc R . . H21C H 0.0275 0.3214 0.1659 0.264 Uiso 1 1 calc R . . C8 C 0.1481(5) 1.0930(9) 0.2383(5) 0.124(4) Uani 1 1 d . . . H8 H 0.1088 1.1297 0.1997 0.148 Uiso 1 1 calc R . . N1 N 0.1288(4) 1.0970(7) 0.3177(4) 0.129(3) Uani 1 1 d . . . H1N H 0.1100 1.1477 0.3385 0.155 Uiso 1 1 calc R . . C9 C 0.2738(5) 1.0634(9) 0.2021(5) 0.135(4) Uani 1 1 d . . . H9A H 0.3237 1.0468 0.2378 0.162 Uiso 1 1 calc R . . H9B H 0.2874 1.0935 0.1541 0.162 Uiso 1 1 calc R . . O1 O 0.2280(4) 1.1277(6) 0.2397(4) 0.169(3) Uani 1 1 d . . . C10 C 0.2224(4) 0.9709(8) 0.1800(4) 0.106(3) Uani 1 1 d . . . C11 C 0.2439(4) 0.8994(9) 0.1361(4) 0.119(4) Uani 1 1 d . . . H11 H 0.2933 0.9067 0.1190 0.143 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 S 0.0810(14) 0.264(3) 0.0439(9) -0.0372(16) -0.0030(9) 0.0630(18) N2 0.058(3) 0.206(7) 0.045(3) -0.019(4) 0.007(2) 0.035(4) C1 0.060(4) 0.202(10) 0.045(4) -0.009(5) 0.012(3) -0.004(5) C13 0.054(4) 0.231(11) 0.056(4) -0.039(5) 0.013(3) 0.012(5) C5 0.105(7) 0.276(16) 0.046(5) -0.009(8) 0.017(5) -0.083(9) C2 0.057(4) 0.204(11) 0.044(4) -0.017(6) 0.006(3) -0.023(6) C12 0.054(5) 0.241(12) 0.058(4) -0.007(6) 0.009(3) 0.036(6) C4 0.094(5) 0.210(10) 0.046(4) 0.002(5) 0.010(4) -0.059(6) C3 0.066(5) 0.215(12) 0.049(5) -0.014(6) 0.008(4) -0.029(6) C7 0.079(5) 0.192(11) 0.060(5) -0.023(6) 0.016(4) -0.045(6) C14 0.055(4) 0.240(12) 0.047(4) -0.017(5) 0.011(3) 0.017(5) C6 0.107(7) 0.261(15) 0.044(5) -0.035(7) 0.024(4) -0.078(9) C18 0.081(7) 0.206(14) 0.112(8) -0.092(9) -0.019(6) 0.017(9) O3 0.120(4) 0.278(8) 0.045(2) -0.016(4) 0.019(3) 0.084(5) O2 0.082(3) 0.247(7) 0.063(3) -0.051(4) -0.021(2) 0.068(4) C19 0.088(7) 0.244(16) 0.084(7) -0.074(8) -0.023(6) 0.059(9) C15 0.077(6) 0.237(12) 0.049(4) -0.047(6) -0.022(4) 0.059(7) C20 0.080(6) 0.272(16) 0.069(6) -0.047(7) -0.014(5) 0.067(9) C16 0.074(6) 0.206(14) 0.122(9) -0.085(9) 0.008(6) 0.027(8) C17 0.073(7) 0.192(14) 0.161(11) -0.087(10) 0.001(6) 0.005(9) C21 0.131(9) 0.184(13) 0.195(12) -0.091(10) -0.021(8) 0.008(9) C8 0.081(6) 0.218(12) 0.073(5) -0.014(6) 0.016(4) -0.016(7) N1 0.121(6) 0.204(10) 0.068(5) -0.036(5) 0.032(4) -0.024(6) C9 0.075(6) 0.243(13) 0.086(6) 0.047(7) 0.014(5) -0.002(8) O1 0.126(6) 0.225(8) 0.171(6) -0.027(6) 0.071(5) -0.049(5) C10 0.058(5) 0.215(11) 0.043(4) 0.017(5) 0.009(4) 0.013(6) C11 0.054(5) 0.250(13) 0.053(5) 0.024(6) 0.013(4) 0.023(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S O2 1.426(4) . ? S O3 1.439(4) . ? S N2 1.645(6) . ? S C15 1.767(11) . ? N2 C13 1.472(7) . ? N2 C12 1.475(7) . ? C1 C10 1.492(9) . ? C1 C14 1.530(9) . ? C1 C8 1.540(11) . ? C1 C2 1.550(10) . ? C13 C14 1.515(10) . ? C5 C6 1.356(14) . ? C5 C4 1.394(13) . ? C2 C3 1.366(11) . ? C2 C7 1.391(11) . ? C12 C11 1.499(11) . ? C4 C3 1.405(9) . ? C7 C6 1.388(10) . ? C7 N1 1.390(11) . ? C18 C17 1.383(13) . ? C18 C19 1.417(14) . ? C18 C21 1.508(13) . ? C19 C20 1.355(14) . ? C15 C20 1.375(11) . ? C15 C16 1.404(12) . ? C16 C17 1.365(13) . ? C8 O1 1.417(9) . ? C8 N1 1.437(9) . ? C9 O1 1.390(10) . ? C9 C10 1.535(11) . ? C10 C11 1.313(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 O2 S O3 118.9(3) . . ? O2 S N2 106.8(3) . . ? O3 S N2 106.4(3) . . ? O2 S C15 109.5(4) . . ? O3 S C15 108.0(4) . . ? N2 S C15 106.5(3) . . ? C13 N2 C12 115.5(5) . . ? C13 N2 S 115.1(5) . . ? C12 N2 S 115.5(5) . . ? C10 C1 C14 114.9(6) . . ? C10 C1 C8 104.1(8) . . ? C14 C1 C8 110.2(7) . . ? C10 C1 C2 112.7(6) . . ? C14 C1 C2 112.3(6) . . ? C8 C1 C2 101.4(7) . . ? N2 C13 C14 112.2(7) . . ? C6 C5 C4 120.5(9) . . ? C3 C2 C7 119.9(8) . . ? C3 C2 C1 131.6(9) . . ? C7 C2 C1 108.4(9) . . ? N2 C12 C11 114.0(7) . . ? C5 C4 C3 119.7(10) . . ? C2 C3 C4 119.4(9) . . ? C6 C7 N1 129.1(11) . . ? C6 C7 C2 120.5(11) . . ? N1 C7 C2 110.3(8) . . ? C13 C14 C1 116.9(7) . . ? C5 C6 C7 119.8(12) . . ? C17 C18 C19 115.6(13) . . ? C17 C18 C21 124.0(13) . . ? C19 C18 C21 120.5(11) . . ? C20 C19 C18 122.1(11) . . ? C20 C15 C16 120.4(11) . . ? C20 C15 S 120.2(9) . . ? C16 C15 S 119.4(8) . . ? C19 C20 C15 120.1(12) . . ? C17 C16 C15 117.7(11) . . ? C16 C17 C18 124.2(14) . . ? O1 C8 N1 109.8(7) . . ? O1 C8 C1 106.5(8) . . ? N1 C8 C1 105.5(8) . . ? C7 N1 C8 110.3(8) . . ? O1 C9 C10 107.2(7) . . ? C9 O1 C8 112.3(8) . . ? C11 C10 C1 130.5(10) . . ? C11 C10 C9 123.2(8) . . ? C1 C10 C9 106.3(8) . . ? C10 C11 C12 127.3(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.88 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.256 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.045 #===END data_comp-5a _database_code_depnum_ccdc_archive 'CCDC 814207' #TrackingRef 'comp2c-5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H31 N O5' _chemical_formula_weight 413.50 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 17.796(6) _cell_length_b 6.2520(18) _cell_length_c 20.307(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.601(4) _cell_angle_gamma 90.00 _cell_volume 2259.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.989 _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 'Bruker SMART Apex II CCD' _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 10746 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.41 _reflns_number_total 4162 _reflns_number_gt 3442 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT+ _computing_structure_solution 'SIR-97 (Giacovazzo, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (Keller 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0511P)^2^+0.1715P] 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 ? _chemical_absolute_configuration unk _refine_ls_number_reflns 4162 _refine_ls_number_parameters 278 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 O2 O 0.59019(8) 0.9706(3) 0.65920(8) 0.0684(5) Uani 1 1 d . . . O3 O 0.66858(7) 0.7056(2) 0.62993(6) 0.0546(4) Uani 1 1 d . . . O4 O 0.80548(8) 0.9748(3) 0.67020(8) 0.0608(4) Uani 1 1 d . . . O5 O 0.80859(6) 0.6700(2) 0.72950(6) 0.0465(3) Uani 1 1 d . . . O1 O 0.59079(8) 1.1333(3) 0.92778(7) 0.0612(4) Uani 1 1 d . . . N1 N 0.68963(11) 1.3586(3) 0.90150(8) 0.0619(5) Uani 1 1 d . . . H1N H 0.6860 1.4937 0.9088 0.074 Uiso 1 1 calc R . . C1 C 0.67500(10) 1.0472(3) 0.83786(9) 0.0410(4) Uani 1 1 d . . . C13 C 0.69593(9) 0.8782(3) 0.72913(8) 0.0390(4) Uani 1 1 d . . . C21 C 0.88743(10) 0.6131(3) 0.71253(11) 0.0527(5) Uani 1 1 d . . . C20 C 0.77660(10) 0.8462(3) 0.70605(9) 0.0425(4) Uani 1 1 d . . . C12 C 0.66474(11) 0.7094(3) 0.77884(9) 0.0435(4) Uani 1 1 d . . . H12A H 0.6274 0.6183 0.7579 0.052 Uiso 1 1 calc R . . H12B H 0.7049 0.6207 0.7965 0.052 Uiso 1 1 calc R . . C3 C 0.80342(11) 0.8883(4) 0.88476(10) 0.0512(5) Uani 1 1 d . . . H3 H 0.8001 0.7593 0.8621 0.061 Uiso 1 1 calc R . . C7 C 0.75279(12) 1.2307(3) 0.91387(9) 0.0510(5) Uani 1 1 d . . . C11 C 0.63036(10) 0.8422(3) 0.83169(8) 0.0421(4) Uani 1 1 d . . . C2 C 0.74771(10) 1.0399(3) 0.87855(9) 0.0429(4) Uani 1 1 d . . . C16 C 0.62552(12) 0.6298(4) 0.57211(10) 0.0605(6) Uani 1 1 d . . . C10 C 0.56499(11) 0.8175(4) 0.86107(10) 0.0525(5) Uani 1 1 d . . . H10 H 0.5369 0.6944 0.8532 0.063 Uiso 1 1 calc R . . C9 C 0.53557(12) 0.9840(4) 0.90663(11) 0.0634(6) Uani 1 1 d . . . H9A H 0.4951 1.0607 0.8846 0.076 Uiso 1 1 calc R . . H9B H 0.5147 0.9141 0.9450 0.076 Uiso 1 1 calc R . . C6 C 0.81379(14) 1.2764(4) 0.95430(10) 0.0638(6) Uani 1 1 d . . . H6 H 0.8171 1.4047 0.9773 0.077 Uiso 1 1 calc R . . C8 C 0.63185(12) 1.2228(3) 0.87425(9) 0.0527(5) Uani 1 1 d . . . H8 H 0.5987 1.3022 0.8442 0.063 Uiso 1 1 calc R . . C5 C 0.86980(14) 1.1222(5) 0.95894(11) 0.0674(7) Uani 1 1 d . . . H5 H 0.9118 1.1490 0.9853 0.081 Uiso 1 1 calc R . . C22 C 0.94036(11) 0.7869(4) 0.73712(12) 0.0632(6) Uani 1 1 d . . . H22A H 0.9914 0.7399 0.7326 0.095 Uiso 1 1 calc R . . H22B H 0.9305 0.8161 0.7826 0.095 Uiso 1 1 calc R . . H22C H 0.9326 0.9146 0.7117 0.095 Uiso 1 1 calc R . . C4 C 0.86500(12) 0.9317(4) 0.92572(11) 0.0630(6) Uani 1 1 d . . . H4 H 0.9030 0.8308 0.9305 0.076 Uiso 1 1 calc R . . C23 C 0.89917(13) 0.4095(4) 0.75094(17) 0.0838(8) Uani 1 1 d . . . H23A H 0.8655 0.3014 0.7346 0.126 Uiso 1 1 calc R . . H23B H 0.8894 0.4353 0.7967 0.126 Uiso 1 1 calc R . . H23C H 0.9501 0.3620 0.7460 0.126 Uiso 1 1 calc R . . C24 C 0.89250(14) 0.5764(6) 0.63963(13) 0.0903(10) Uani 1 1 d . . . H24A H 0.8574 0.4672 0.6267 0.135 Uiso 1 1 calc R . . H24B H 0.9425 0.5319 0.6289 0.135 Uiso 1 1 calc R . . H24C H 0.8808 0.7067 0.6167 0.135 Uiso 1 1 calc R . . C17 C 0.55366(14) 0.5320(5) 0.59518(14) 0.0823(8) Uani 1 1 d . . . H17A H 0.5222 0.6412 0.6134 0.123 Uiso 1 1 calc R . . H17B H 0.5645 0.4263 0.6282 0.123 Uiso 1 1 calc R . . H17C H 0.5282 0.4656 0.5586 0.123 Uiso 1 1 calc R . . C19 C 0.67713(18) 0.4625(7) 0.54370(17) 0.1132(13) Uani 1 1 d . . . H19A H 0.6893 0.3586 0.5770 0.170 Uiso 1 1 calc R . . H19B H 0.7224 0.5296 0.5288 0.170 Uiso 1 1 calc R . . H19C H 0.6525 0.3930 0.5073 0.170 Uiso 1 1 calc R . . C18 C 0.61213(18) 0.8120(6) 0.52442(12) 0.0964(10) Uani 1 1 d . . . H18A H 0.6587 0.8850 0.5166 0.145 Uiso 1 1 calc R . . H18B H 0.5766 0.9103 0.5428 0.145 Uiso 1 1 calc R . . H18C H 0.5927 0.7565 0.4836 0.145 Uiso 1 1 calc R . . C15 C 0.64543(10) 0.8634(3) 0.66848(9) 0.0443(4) Uani 1 1 d . . . C14 C 0.68843(11) 1.0967(3) 0.76438(9) 0.0445(5) Uani 1 1 d . . . H14A H 0.7339 1.1802 0.7593 0.053 Uiso 1 1 calc R . . H14B H 0.6466 1.1770 0.7460 0.053 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 O2 0.0507(8) 0.0792(11) 0.0748(10) -0.0052(9) -0.0136(7) 0.0253(9) O3 0.0464(7) 0.0685(10) 0.0489(7) -0.0159(7) -0.0066(6) 0.0094(7) O4 0.0463(8) 0.0655(10) 0.0707(10) 0.0147(8) 0.0128(7) 0.0060(8) O5 0.0323(6) 0.0473(8) 0.0599(8) -0.0038(6) 0.0002(6) 0.0088(6) O1 0.0668(9) 0.0714(10) 0.0458(8) -0.0002(7) 0.0158(7) 0.0157(9) N1 0.0892(13) 0.0378(9) 0.0589(10) -0.0086(9) 0.0069(9) 0.0095(10) C1 0.0473(10) 0.0383(10) 0.0374(9) 0.0002(8) 0.0043(8) 0.0079(8) C13 0.0387(9) 0.0384(10) 0.0398(9) 0.0008(8) 0.0015(7) 0.0058(8) C21 0.0300(9) 0.0573(13) 0.0708(13) -0.0131(11) -0.0009(9) 0.0119(9) C20 0.0359(9) 0.0472(11) 0.0444(10) -0.0025(10) 0.0003(8) 0.0046(9) C12 0.0453(10) 0.0381(10) 0.0471(10) 0.0023(9) 0.0027(8) 0.0042(8) C3 0.0516(11) 0.0541(12) 0.0479(11) -0.0007(10) -0.0009(9) 0.0071(10) C7 0.0665(13) 0.0440(12) 0.0428(10) 0.0017(9) 0.0090(10) 0.0006(10) C11 0.0418(10) 0.0426(10) 0.0420(10) 0.0078(9) 0.0014(8) 0.0105(9) C2 0.0487(11) 0.0426(11) 0.0375(10) 0.0024(8) 0.0031(8) 0.0008(9) C16 0.0562(12) 0.0808(16) 0.0445(11) -0.0096(11) -0.0041(9) -0.0120(12) C10 0.0450(11) 0.0570(13) 0.0557(11) 0.0116(10) 0.0058(9) 0.0068(10) C9 0.0512(12) 0.0821(17) 0.0573(13) 0.0086(12) 0.0153(10) 0.0152(13) C6 0.0848(17) 0.0581(14) 0.0486(12) -0.0067(11) 0.0019(11) -0.0214(13) C8 0.0662(13) 0.0479(12) 0.0441(10) 0.0011(10) 0.0087(10) 0.0189(11) C5 0.0595(14) 0.0881(19) 0.0546(13) 0.0001(13) -0.0047(11) -0.0178(14) C22 0.0374(11) 0.0686(15) 0.0836(15) -0.0069(13) -0.0014(10) 0.0007(10) C4 0.0533(12) 0.0792(18) 0.0565(13) 0.0019(12) -0.0041(10) 0.0045(11) C23 0.0475(13) 0.0584(15) 0.145(3) 0.0003(16) -0.0086(14) 0.0150(11) C24 0.0559(14) 0.129(3) 0.0860(18) -0.0436(19) 0.0016(12) 0.0233(16) C17 0.0745(16) 0.092(2) 0.0801(17) 0.0050(16) -0.0076(13) -0.0283(16) C19 0.096(2) 0.145(3) 0.098(2) -0.072(2) -0.0004(17) 0.004(2) C18 0.114(2) 0.124(3) 0.0514(13) 0.0185(16) -0.0151(14) -0.044(2) C15 0.0389(10) 0.0500(11) 0.0441(10) 0.0023(9) 0.0035(8) 0.0068(9) C14 0.0519(11) 0.0395(10) 0.0422(10) 0.0027(8) 0.0034(8) 0.0092(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 C15 1.203(2) . ? O3 C15 1.328(2) . ? O3 C16 1.473(2) . ? O4 C20 1.204(2) . ? O5 C20 1.326(2) . ? O5 C21 1.491(2) . ? O1 C9 1.419(3) . ? O1 C8 1.430(2) . ? N1 C7 1.400(3) . ? N1 C8 1.440(3) . ? N1 H1N 0.8600 . ? C1 C11 1.512(3) . ? C1 C2 1.529(3) . ? C1 C8 1.534(3) . ? C1 C14 1.545(3) . ? C13 C15 1.520(2) . ? C13 C20 1.528(2) . ? C13 C14 1.549(3) . ? C13 C12 1.566(3) . ? C21 C24 1.502(3) . ? C21 C23 1.506(3) . ? C21 C22 1.519(3) . ? C12 C11 1.493(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C3 C2 1.376(3) . ? C3 C4 1.395(3) . ? C3 H3 0.9300 . ? C7 C6 1.384(3) . ? C7 C2 1.394(3) . ? C11 C10 1.322(3) . ? C16 C17 1.497(3) . ? C16 C19 1.511(4) . ? C16 C18 1.512(4) . ? C10 C9 1.491(3) . ? C10 H10 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C6 C5 1.389(4) . ? C6 H6 0.9300 . ? C8 H8 0.9800 . ? C5 C4 1.371(4) . ? C5 H5 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C4 H4 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 C15 O3 C16 123.14(16) . . ? C20 O5 C21 121.10(15) . . ? C9 O1 C8 112.64(16) . . ? C7 N1 C8 107.51(17) . . ? C7 N1 H1N 126.2 . . ? C8 N1 H1N 126.2 . . ? C11 C1 C2 117.41(16) . . ? C11 C1 C8 112.42(15) . . ? C2 C1 C8 100.73(15) . . ? C11 C1 C14 100.14(15) . . ? C2 C1 C14 112.92(15) . . ? C8 C1 C14 113.91(15) . . ? C15 C13 C20 107.03(14) . . ? C15 C13 C14 112.03(15) . . ? C20 C13 C14 110.06(16) . . ? C15 C13 C12 105.71(15) . . ? C20 C13 C12 116.74(15) . . ? C14 C13 C12 105.29(14) . . ? O5 C21 C24 109.31(16) . . ? O5 C21 C23 101.99(18) . . ? C24 C21 C23 111.8(2) . . ? O5 C21 C22 109.57(16) . . ? C24 C21 C22 112.9(2) . . ? C23 C21 C22 110.62(19) . . ? O4 C20 O5 125.99(16) . . ? O4 C20 C13 120.45(17) . . ? O5 C20 C13 113.56(16) . . ? C11 C12 C13 103.83(15) . . ? C11 C12 H12A 111.0 . . ? C13 C12 H12A 111.0 . . ? C11 C12 H12B 111.0 . . ? C13 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? C2 C3 C4 118.7(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C6 C7 C2 121.9(2) . . ? C6 C7 N1 127.7(2) . . ? C2 C7 N1 110.41(18) . . ? C10 C11 C12 128.9(2) . . ? C10 C11 C1 121.70(18) . . ? C12 C11 C1 108.18(15) . . ? C3 C2 C7 119.96(18) . . ? C3 C2 C1 132.45(18) . . ? C7 C2 C1 107.60(17) . . ? O3 C16 C17 108.71(18) . . ? O3 C16 C19 102.34(19) . . ? C17 C16 C19 111.2(3) . . ? O3 C16 C18 110.2(2) . . ? C17 C16 C18 112.3(2) . . ? C19 C16 C18 111.7(2) . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? O1 C9 C10 113.62(17) . . ? O1 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? O1 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C7 C6 C5 117.1(2) . . ? C7 C6 H6 121.5 . . ? C5 C6 H6 121.5 . . ? O1 C8 N1 107.88(16) . . ? O1 C8 C1 110.41(17) . . ? N1 C8 C1 104.37(16) . . ? O1 C8 H8 111.3 . . ? N1 C8 H8 111.3 . . ? C1 C8 H8 111.3 . . ? C4 C5 C6 121.9(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O2 C15 O3 125.44(18) . . ? O2 C15 C13 124.62(18) . . ? O3 C15 C13 109.79(15) . . ? C1 C14 C13 106.54(15) . . ? C1 C14 H14A 110.4 . . ? C13 C14 H14A 110.4 . . ? C1 C14 H14B 110.4 . . ? C13 C14 H14B 110.4 . . ? H14A C14 H14B 108.6 . . ? 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 C20 O5 C21 C24 -62.9(3) . . . . ? C20 O5 C21 C23 178.58(18) . . . . ? C20 O5 C21 C22 61.3(2) . . . . ? C21 O5 C20 O4 0.0(3) . . . . ? C21 O5 C20 C13 -179.67(15) . . . . ? C15 C13 C20 O4 65.2(2) . . . . ? C14 C13 C20 O4 -56.7(2) . . . . ? C12 C13 C20 O4 -176.64(17) . . . . ? C15 C13 C20 O5 -115.07(17) . . . . ? C14 C13 C20 O5 122.96(17) . . . . ? C12 C13 C20 O5 3.1(2) . . . . ? C15 C13 C12 C11 -109.26(16) . . . . ? C20 C13 C12 C11 131.90(16) . . . . ? C14 C13 C12 C11 9.49(18) . . . . ? C8 N1 C7 C6 -162.2(2) . . . . ? C8 N1 C7 C2 18.1(2) . . . . ? C13 C12 C11 C10 135.5(2) . . . . ? C13 C12 C11 C1 -32.08(18) . . . . ? C2 C1 C11 C10 109.7(2) . . . . ? C8 C1 C11 C10 -6.5(2) . . . . ? C14 C1 C11 C10 -127.74(18) . . . . ? C2 C1 C11 C12 -81.63(19) . . . . ? C8 C1 C11 C12 162.22(15) . . . . ? C14 C1 C11 C12 40.94(17) . . . . ? C4 C3 C2 C7 -1.3(3) . . . . ? C4 C3 C2 C1 178.56(19) . . . . ? C6 C7 C2 C3 1.7(3) . . . . ? N1 C7 C2 C3 -178.56(17) . . . . ? C6 C7 C2 C1 -178.11(18) . . . . ? N1 C7 C2 C1 1.6(2) . . . . ? C11 C1 C2 C3 39.0(3) . . . . ? C8 C1 C2 C3 161.3(2) . . . . ? C14 C1 C2 C3 -76.8(3) . . . . ? C11 C1 C2 C7 -141.22(16) . . . . ? C8 C1 C2 C7 -18.85(18) . . . . ? C14 C1 C2 C7 103.02(17) . . . . ? C15 O3 C16 C17 -65.6(3) . . . . ? C15 O3 C16 C19 176.7(2) . . . . ? C15 O3 C16 C18 57.8(3) . . . . ? C12 C11 C10 C9 -171.66(18) . . . . ? C1 C11 C10 C9 -5.5(3) . . . . ? C8 O1 C9 C10 50.5(2) . . . . ? C11 C10 C9 O1 -15.7(3) . . . . ? C2 C7 C6 C5 -0.7(3) . . . . ? N1 C7 C6 C5 179.62(19) . . . . ? C9 O1 C8 N1 -175.75(16) . . . . ? C9 O1 C8 C1 -62.3(2) . . . . ? C7 N1 C8 O1 87.69(18) . . . . ? C7 N1 C8 C1 -29.8(2) . . . . ? C11 C1 C8 O1 39.0(2) . . . . ? C2 C1 C8 O1 -86.81(19) . . . . ? C14 C1 C8 O1 152.02(17) . . . . ? C11 C1 C8 N1 154.68(15) . . . . ? C2 C1 C8 N1 28.88(18) . . . . ? C14 C1 C8 N1 -92.29(19) . . . . ? C7 C6 C5 C4 -0.7(3) . . . . ? C6 C5 C4 C3 1.2(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C16 O3 C15 O2 -4.7(3) . . . . ? C16 O3 C15 C13 171.08(17) . . . . ? C20 C13 C15 O2 -142.9(2) . . . . ? C14 C13 C15 O2 -22.1(3) . . . . ? C12 C13 C15 O2 92.0(2) . . . . ? C20 C13 C15 O3 41.3(2) . . . . ? C14 C13 C15 O3 162.06(15) . . . . ? C12 C13 C15 O3 -83.77(17) . . . . ? C11 C1 C14 C13 -33.36(18) . . . . ? C2 C1 C14 C13 92.33(19) . . . . ? C8 C1 C14 C13 -153.56(17) . . . . ? C15 C13 C14 C1 129.69(16) . . . . ? C20 C13 C14 C1 -111.35(17) . . . . ? C12 C13 C14 C1 15.27(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.41 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.216 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.030 #===END