                                                                                
data_sdemo                                                                      
                                                                                
_audit_creation_method            SHELXL-97                                     
_chemical_name_systematic                                                       
;                                                                               
 ?                                                                              
;                                                                               
_chemical_name_common             ?                                             
_chemical_melting_point           ?                                             
_chemical_formula_moiety          ?                                             
_chemical_formula_sum                                                           
 'C20 H24 O12'                                                                  
_chemical_formula_weight          456.39                                        
                                                                                
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'                        
 'O'  'O'   0.0106   0.0060                                                     
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'                        
                                                                                
_symmetry_cell_setting            ?                                             
_symmetry_space_group_name_H-M    ?                                             
                                                                                
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                    4.0007(10)                                    
_cell_length_b                    7.7300(8)                                     
_cell_length_c                    16.952(2)                                     
_cell_angle_alpha                 90.00                                         
_cell_angle_beta                  99.540(17)                                    
_cell_angle_gamma                 90.00                                         
_cell_volume                      517.00(15)                                    
_cell_formula_units_Z             1                                             
_cell_measurement_temperature     293(2)                                        
_cell_measurement_reflns_used     ?                                             
_cell_measurement_theta_min       ?                                             
_cell_measurement_theta_max       ?                                             
                                                                                
_exptl_crystal_description        ?                                             
_exptl_crystal_colour             ?                                             
_exptl_crystal_size_max           ?                                             
_exptl_crystal_size_mid           ?                                             
_exptl_crystal_size_min           ?                                             
_exptl_crystal_density_meas       ?                                             
_exptl_crystal_density_diffrn     1.466                                         
_exptl_crystal_density_method     'not measured'                                
_exptl_crystal_F_000              240                                           
_exptl_absorpt_coefficient_mu     0.123                                         
_exptl_absorpt_correction_type    ?                                             
_exptl_absorpt_correction_T_min   ?                                             
_exptl_absorpt_correction_T_max   ?                                             
_exptl_absorpt_process_details    ?                                             
                                                                                
_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   ?                                             
_diffrn_measurement_method        ?                                             
_diffrn_detector_area_resol_mean  ?                                             
_diffrn_standards_number          ?                                             
_diffrn_standards_interval_count  ?                                             
_diffrn_standards_interval_time   ?                                             
_diffrn_standards_decay_%         ?                                             
_diffrn_reflns_number             2710                                          
_diffrn_reflns_av_R_equivalents   0.0565                                        
_diffrn_reflns_av_sigmaI/netI     0.0572                                        
_diffrn_reflns_limit_h_min        -5                                            
_diffrn_reflns_limit_h_max        5                                             
_diffrn_reflns_limit_k_min        -10                                           
_diffrn_reflns_limit_k_max        0                                             
_diffrn_reflns_limit_l_min        -22                                           
_diffrn_reflns_limit_l_max        22                                            
_diffrn_reflns_theta_min          2.44                                          
_diffrn_reflns_theta_max          27.51                                         
_reflns_number_total              1192                                          
_reflns_number_gt                 738                                           
_reflns_threshold_expression      >2sigma(I)                                    
                                                                                
_computing_data_collection        ?                                             
_computing_cell_refinement        ?                                             
_computing_data_reduction         ?                                             
_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)+(0.0590P)²+0.1050P] where P=(Fo²+2Fc²)/3'        
_atom_sites_solution_primary      direct                                        
_atom_sites_solution_secondary    difmap                                        
_atom_sites_solution_hydrogens    geom                                          
_refine_ls_hydrogen_treatment     mixed                                         
_refine_ls_extinction_method      none                                          
_refine_ls_extinction_coef        ?                                             
_refine_ls_number_reflns          1192                                          
_refine_ls_number_parameters      97                                            
_refine_ls_number_restraints      0                                             
_refine_ls_R_factor_all           0.0893                                        
_refine_ls_R_factor_gt            0.0440                                        
_refine_ls_wR_factor_ref          0.1298                                        
_refine_ls_wR_factor_gt           0.1101                                        
_refine_ls_goodness_of_fit_ref    1.012                                         
_refine_ls_restrained_S_all       1.012                                         
_refine_ls_shift/su_max           0.007                                         
_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                                                      
O501 O -0.0197(4) 0.85748(17) 0.15198(7) 0.0415(4) Uani 1 1 d . . .             
O502 O 0.2562(4) 0.66866(18) 0.02539(9) 0.0497(5) Uani 1 1 d . . .              
O503 O -0.2535(4) 1.1764(2) 0.10873(9) 0.0524(5) Uani 1 1 d . . .               
C501 C 0.1272(5) 0.8287(2) 0.02203(11) 0.0335(4) Uani 1 1 d . . .               
C502 C 0.0084(5) 0.9214(2) 0.07805(10) 0.0325(4) Uani 1 1 d . . .               
C503 C -0.1294(5) 1.0959(2) 0.05942(10) 0.0337(4) Uani 1 1 d . . .              
C504 C 0.3000(8) 0.5680(3) 0.09717(14) 0.0464(5) Uani 1 1 d . . .               
C505 C 0.1975(8) 0.9374(4) 0.21834(13) 0.0527(6) Uani 1 1 d . . .               
H501 H 0.411(6) 0.463(3) 0.0838(14) 0.050 Uiso 0.96(4) 1 d P . .                
H502 H 0.081(8) 0.542(3) 0.1131(16) 0.050 Uiso 0.87(4) 1 d P . .                
H503 H 0.441(8) 0.633(3) 0.1407(18) 0.050 Uiso 0.84(5) 1 d P . .                
H504 H 0.122(9) 1.046(5) 0.2311(19) 0.050 Uiso 0.74(5) 1 d P . .                
H505 H 0.212(8) 0.863(4) 0.261(2) 0.050 Uiso 0.72(5) 1 d P . .                  
H506 H 0.409(12) 0.973(5) 0.208(2) 0.050 Uiso 0.60(5) 1 d P . .                 
                                                                                
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                                                          
O501 0.0551(9) 0.0418(8) 0.0285(7) 0.0025(6) 0.0098(6) -0.0013(7)               
O502 0.0758(11) 0.0345(8) 0.0407(8) 0.0025(6) 0.0158(8) 0.0168(7)               
O503 0.0761(12) 0.0481(9) 0.0372(8) -0.0014(7) 0.0214(8) 0.0175(8)              
C501 0.0379(10) 0.0302(9) 0.0318(9) -0.0012(8) 0.0039(8) 0.0011(8)              
C502 0.0359(10) 0.0336(10) 0.0281(9) 0.0007(8) 0.0055(7) -0.0017(8)             
C503 0.0387(10) 0.0343(10) 0.0287(9) -0.0039(8) 0.0066(8) 0.0000(8)             
C504 0.0587(15) 0.0370(12) 0.0430(12) 0.0065(10) 0.0073(11) 0.0093(12)          
C505 0.0637(18) 0.0647(17) 0.0272(10) -0.0015(12) 0.0004(10) 0.0028(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                                                           
O501 C502 1.369(2) . ?                                                          
O501 C505 1.442(3) . ?                                                          
O502 C501 1.338(2) . ?                                                          
O502 C504 1.430(2) . ?                                                          
O503 C503 1.213(2) . ?                                                          
C501 C502 1.338(3) . ?                                                          
C501 C503 1.500(3) 3_575 ?                                                      
C502 C503 1.471(3) . ?                                                          
C503 C501 1.500(3) 3_575 ?                                                      
                                                                                
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                                                          
C502 O501 C505 115.44(18) . . ?                                                 
C501 O502 C504 122.08(17) . . ?                                                 
C502 C501 O502 130.14(18) . . ?                                                 
C502 C501 C503 120.14(17) . 3_575 ?                                             
O502 C501 C503 109.71(16) . 3_575 ?                                             
C501 C502 O501 123.31(17) . . ?                                                 
C501 C502 C503 120.20(16) . . ?                                                 
O501 C502 C503 116.28(15) . . ?                                                 
O503 C503 C502 120.29(16) . . ?                                                 
O503 C503 C501 120.03(18) . 3_575 ?                                             
C502 C503 C501 119.64(15) . 3_575 ?                                             
                                                                                
_diffrn_measured_fraction_theta_max    1.000                                    
_diffrn_reflns_theta_full              27.51                                    
_diffrn_measured_fraction_theta_full   1.000                                    
_refine_diff_density_max    0.225                                               
_refine_diff_density_min   -0.176                                               
_refine_diff_density_rms    0.047                                               
