 
data_01esp301 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
Pedro Cintas
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C28 H32 N2 O11 S' 
_chemical_formula_weight          604.62 
 
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                    10.9877(7) 
_cell_length_b                    11.9703(8) 
_cell_length_c                    22.4663(18) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2954.9(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     16617 
_cell_measurement_theta_min       1.02 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.60 
_exptl_crystal_size_mid           0.07 
_exptl_crystal_size_min           0.07 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.359 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1272 
_exptl_absorpt_coefficient_mu     0.172 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9038 
_exptl_absorpt_correction_T_max   0.9881 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             13093 
_diffrn_reflns_av_R_equivalents   0.2525 
_diffrn_reflns_av_sigmaI/netI     0.4831 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -26 
_diffrn_reflns_limit_l_max        26 
_diffrn_reflns_theta_min          3.10 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              5105 
_reflns_number_gt                 1634 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0421P)²+0.0000P] where P=(Fo²+2Fc²)/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_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.1(2) 
_refine_ls_number_reflns          5105 
_refine_ls_number_parameters      379 
_refine_ls_number_restraints      234 
_refine_ls_R_factor_all           0.3088 
_refine_ls_R_factor_gt            0.0848 
_refine_ls_wR_factor_ref          0.1930 
_refine_ls_wR_factor_gt           0.1318 
_refine_ls_goodness_of_fit_ref    0.904 
_refine_ls_restrained_S_all       0.907 
_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 
C1 C 0.8692(9) 0.5161(8) 0.1504(5) 0.026(3) Uani 1 1 d U . . 
C2 C 0.8589(10) 0.5005(8) 0.2105(5) 0.040(3) Uani 1 1 d U . . 
H2 H 0.8296 0.5586 0.2355 0.048 Uiso 1 1 calc R . . 
C3 C 0.8924(10) 0.3974(8) 0.2344(5) 0.046(3) Uani 1 1 d U . . 
H3 H 0.8815 0.3842 0.2757 0.055 Uiso 1 1 calc R . . 
C4 C 0.9411(10) 0.3142(8) 0.1992(5) 0.044(3) Uani 1 1 d U . . 
H4 H 0.9691 0.2462 0.2161 0.053 Uiso 1 1 calc R . . 
C5 C 0.9481(11) 0.3323(9) 0.1393(5) 0.054(4) Uani 1 1 d U . . 
H5 H 0.9766 0.2745 0.1139 0.065 Uiso 1 1 calc R . . 
C6 C 0.9134(9) 0.4362(8) 0.1146(5) 0.038(3) Uani 1 1 d U . . 
H6 H 0.9213 0.4492 0.0731 0.045 Uiso 1 1 calc R . . 
C7 C 0.8383(10) 0.6284(8) 0.1236(4) 0.032(3) Uani 1 1 d U . . 
C8 C 0.7700(10) 0.6293(7) 0.0619(4) 0.032(3) Uani 1 1 d U . . 
H8 H 0.8279 0.6090 0.0294 0.038 Uiso 1 1 calc R . . 
C9 C 0.7243(10) 0.7516(6) 0.0530(4) 0.034(3) Uani 1 1 d U . . 
H9A H 0.7589 0.7838 0.0161 0.041 Uiso 1 1 calc R . . 
H9B H 0.6344 0.7534 0.0502 0.041 Uiso 1 1 calc R . . 
C10 C 0.7668(10) 0.8160(7) 0.1065(5) 0.032(3) Uani 1 1 d U . . 
C11 C 0.9454(11) 0.7064(8) 0.1109(5) 0.030(3) Uani 1 1 d U . . 
C12 C 0.6673(12) 0.5509(9) 0.0623(5) 0.041(3) Uani 1 1 d U . . 
C13 C 0.9700(10) 0.8873(7) 0.0651(4) 0.042(3) Uani 1 1 d U . . 
H13A H 0.9311 0.9609 0.0641 0.063 Uiso 1 1 calc R . . 
H13B H 0.9710 0.8554 0.0249 0.063 Uiso 1 1 calc R . . 
H13C H 1.0537 0.8949 0.0797 0.063 Uiso 1 1 calc R . . 
C14 C 0.7170(9) 0.9339(7) 0.1189(4) 0.018(2) Uani 1 1 d U . . 
H14 H 0.7667 0.9897 0.0964 0.022 Uiso 1 1 calc R . . 
C15 C 0.5822(9) 0.9480(7) 0.1021(4) 0.028(3) Uani 1 1 d U . . 
H15 H 0.5707 0.9391 0.0582 0.034 Uiso 1 1 calc R . . 
C16 C 0.4295(9) 0.8005(8) 0.1030(5) 0.031(3) Uani 1 1 d U . . 
C17 C 0.3633(9) 0.7249(8) 0.1438(4) 0.043(3) Uani 1 1 d U . . 
H17A H 0.3905 0.7380 0.1847 0.065 Uiso 1 1 calc R . . 
H17B H 0.3798 0.6472 0.1327 0.065 Uiso 1 1 calc R . . 
H17C H 0.2757 0.7394 0.1409 0.065 Uiso 1 1 calc R . . 
C18 C 0.8223(12) 1.0210(8) 0.1997(5) 0.038(3) Uani 1 1 d U . . 
C19 C 0.8172(9) 1.0334(7) 0.2664(4) 0.037(3) Uani 1 1 d U . . 
H19A H 0.7445 0.9957 0.2817 0.055 Uiso 1 1 calc R . . 
H19B H 0.8139 1.1128 0.2768 0.055 Uiso 1 1 calc R . . 
H19C H 0.8900 0.9996 0.2841 0.055 Uiso 1 1 calc R . . 
C20 C 0.5320(10) 1.0606(7) 0.1231(4) 0.029(3) Uani 1 1 d U . . 
H20 H 0.5329 1.0619 0.1677 0.035 Uiso 1 1 calc R . . 
C21 C 0.3236(12) 1.0907(9) 0.1452(6) 0.044(4) Uani 1 1 d U . . 
C22 C 0.1973(12) 1.0860(9) 0.1189(5) 0.085(5) Uani 1 1 d U . . 
H22A H 0.2023 1.0612 0.0774 0.127 Uiso 1 1 calc R . . 
H22B H 0.1603 1.1605 0.1205 0.127 Uiso 1 1 calc R . . 
H22C H 0.1475 1.0334 0.1417 0.127 Uiso 1 1 calc R . . 
C23 C 0.5938(9) 1.1639(7) 0.1006(4) 0.024(3) Uani 1 1 d U . . 
H23 H 0.6828 1.1610 0.1098 0.029 Uiso 1 1 calc R . . 
C24 C 0.5740(9) 1.1926(7) 0.0350(4) 0.039(3) Uani 1 1 d U . . 
H24A H 0.4857 1.1982 0.0268 0.047 Uiso 1 1 calc R . . 
H24B H 0.6114 1.2660 0.0262 0.047 Uiso 1 1 calc R . . 
C25 C 0.7323(15) 1.1290(10) -0.0276(6) 0.070(4) Uani 1 1 d U . . 
C26 C 0.7731(11) 1.0394(8) -0.0704(4) 0.054(3) Uani 1 1 d U . . 
H26A H 0.7110 0.9807 -0.0725 0.082 Uiso 1 1 calc R . . 
H26B H 0.8500 1.0072 -0.0566 0.082 Uiso 1 1 calc R . . 
H26C H 0.7847 1.0721 -0.1100 0.082 Uiso 1 1 calc R . . 
C27 C 0.5800(11) 1.2818(9) 0.1853(5) 0.040(3) Uani 1 1 d U . . 
C28 C 0.5163(10) 1.3829(7) 0.2113(4) 0.044(3) Uani 1 1 d U . . 
H28A H 0.4562 1.4109 0.1828 0.066 Uiso 1 1 calc R . . 
H28B H 0.5764 1.4414 0.2196 0.066 Uiso 1 1 calc R . . 
H28C H 0.4753 1.3617 0.2483 0.066 Uiso 1 1 calc R . . 
N1 N 0.5872(9) 0.4906(7) 0.0593(4) 0.056(3) Uani 1 1 d . . . 
N2 N 0.9017(8) 0.8133(7) 0.1050(4) 0.040(3) Uani 1 1 d . . . 
O1 O 1.0505(7) 0.6779(5) 0.1053(3) 0.040(2) Uani 1 1 d U . . 
O2 O 0.5121(6) 0.8648(4) 0.1343(3) 0.0252(18) Uani 1 1 d U . . 
O3 O 0.4188(6) 0.8092(5) 0.0492(3) 0.040(2) Uani 1 1 d U . . 
O4 O 0.7260(6) 0.9567(5) 0.1811(3) 0.0314(18) Uani 1 1 d U . . 
O5 O 0.8969(7) 1.0584(5) 0.1670(3) 0.043(2) Uani 1 1 d U . . 
O6 O 0.4065(7) 1.0598(5) 0.1032(3) 0.037(2) Uani 1 1 d U . . 
O7 O 0.3446(7) 1.1190(6) 0.1941(3) 0.053(2) Uani 1 1 d U . . 
O8 O 0.6269(8) 1.1087(5) -0.0028(3) 0.050(2) Uani 1 1 d U . . 
O9 O 0.7847(10) 1.2107(8) -0.0154(5) 0.143(4) Uani 1 1 d U . . 
O10 O 0.5378(6) 1.2618(5) 0.1293(3) 0.034(2) Uani 1 1 d U . . 
O11 O 0.6550(7) 1.2256(5) 0.2102(3) 0.040(2) Uani 1 1 d U . . 
S1 S 0.7370(3) 0.7192(2) 0.16899(12) 0.0370(8) Uani 1 1 d . . . 
 
 
_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 
C1 C6 1.341(11) . ? 
C1 C2 1.368(11) . ? 
C1 C7 1.512(12) . ? 
C2 C3 1.395(12) . ? 
C3 C4 1.380(12) . ? 
C4 C5 1.365(12) . ? 
C5 C6 1.414(12) . ? 
C7 C11 1.529(13) . ? 
C7 C8 1.576(12) . ? 
C7 S1 1.860(10) . ? 
C8 C12 1.467(14) . ? 
C8 C9 1.560(11) . ? 
C9 C10 1.503(12) . ? 
C10 N2 1.483(12) . ? 
C10 C14 1.538(11) . ? 
C10 S1 1.849(10) . ? 
C11 O1 1.211(10) . ? 
C11 N2 1.373(11) . ? 
C12 N1 1.141(12) . ? 
C13 N2 1.466(11) . ? 
C14 O4 1.427(9) . ? 
C14 C15 1.538(11) . ? 
C15 O2 1.453(10) . ? 
C15 C20 1.531(12) . ? 
C16 O3 1.220(11) . ? 
C16 O2 1.382(10) . ? 
C16 C17 1.478(13) . ? 
C18 O5 1.188(11) . ? 
C18 O4 1.374(12) . ? 
C18 C19 1.507(12) . ? 
C20 O6 1.450(11) . ? 
C20 C23 1.499(12) . ? 
C21 O7 1.173(12) . ? 
C21 O6 1.363(12) . ? 
C21 C22 1.509(15) . ? 
C23 O10 1.472(10) . ? 
C23 C24 1.529(11) . ? 
C24 O8 1.439(10) . ? 
C25 O9 1.168(13) . ? 
C25 O8 1.308(14) . ? 
C25 C26 1.509(14) . ? 
C27 O11 1.202(11) . ? 
C27 O10 1.363(12) . ? 
C27 C28 1.515(12) . ? 
 
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 
C6 C1 C2 121.6(10) . . ? 
C6 C1 C7 118.5(9) . . ? 
C2 C1 C7 119.8(9) . . ? 
C1 C2 C3 118.6(10) . . ? 
C4 C3 C2 121.3(11) . . ? 
C5 C4 C3 118.2(10) . . ? 
C4 C5 C6 120.8(10) . . ? 
C1 C6 C5 119.3(10) . . ? 
C1 C7 C11 116.4(9) . . ? 
C1 C7 C8 117.6(8) . . ? 
C11 C7 C8 101.4(8) . . ? 
C1 C7 S1 115.8(7) . . ? 
C11 C7 S1 101.9(6) . . ? 
C8 C7 S1 101.1(6) . . ? 
C12 C8 C9 110.7(9) . . ? 
C12 C8 C7 110.9(9) . . ? 
C9 C8 C7 105.8(7) . . ? 
C10 C9 C8 106.2(8) . . ? 
N2 C10 C9 106.3(9) . . ? 
N2 C10 C14 112.3(8) . . ? 
C9 C10 C14 120.3(8) . . ? 
N2 C10 S1 100.4(7) . . ? 
C9 C10 S1 103.3(6) . . ? 
C14 C10 S1 112.0(7) . . ? 
O1 C11 N2 125.9(10) . . ? 
O1 C11 C7 125.5(9) . . ? 
N2 C11 C7 108.6(9) . . ? 
N1 C12 C8 176.3(13) . . ? 
O4 C14 C10 109.1(7) . . ? 
O4 C14 C15 106.6(7) . . ? 
C10 C14 C15 113.5(8) . . ? 
O2 C15 C20 104.9(7) . . ? 
O2 C15 C14 108.2(7) . . ? 
C20 C15 C14 111.5(8) . . ? 
O3 C16 O2 121.4(9) . . ? 
O3 C16 C17 128.2(10) . . ? 
O2 C16 C17 110.4(9) . . ? 
O5 C18 O4 123.6(11) . . ? 
O5 C18 C19 127.1(12) . . ? 
O4 C18 C19 109.3(10) . . ? 
O6 C20 C23 109.3(8) . . ? 
O6 C20 C15 104.0(8) . . ? 
C23 C20 C15 117.3(8) . . ? 
O7 C21 O6 126.5(12) . . ? 
O7 C21 C22 124.0(13) . . ? 
O6 C21 C22 109.5(11) . . ? 
O10 C23 C20 108.7(8) . . ? 
O10 C23 C24 100.5(7) . . ? 
C20 C23 C24 116.5(8) . . ? 
O8 C24 C23 110.8(8) . . ? 
O9 C25 O8 119.5(13) . . ? 
O9 C25 C26 126.8(15) . . ? 
O8 C25 C26 113.7(11) . . ? 
O11 C27 O10 124.4(10) . . ? 
O11 C27 C28 125.8(11) . . ? 
O10 C27 C28 109.8(10) . . ? 
C11 N2 C13 116.2(9) . . ? 
C11 N2 C10 111.6(8) . . ? 
C13 N2 C10 120.8(9) . . ? 
C16 O2 C15 118.4(7) . . ? 
C18 O4 C14 117.3(8) . . ? 
C21 O6 C20 114.8(9) . . ? 
C25 O8 C24 118.6(8) . . ? 
C27 O10 C23 113.7(8) . . ? 
C10 S1 C7 81.1(4) . . ? 
 
_diffrn_measured_fraction_theta_max    0.991 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.991 
_refine_diff_density_max    0.444 
_refine_diff_density_min   -0.366 
_refine_diff_density_rms    0.078 
