 
data_01src400 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C23 H24 O9' 
_chemical_formula_weight          444.42 
 
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            Orthorhombic
_symmetry_space_group_name_H-M    Pbca
 
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' 
 '-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                    14.1493(4) 
_cell_length_b                    17.3003(6) 
_cell_length_c                    17.4340(7) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      4267.6(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.383 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1872 
_exptl_absorpt_coefficient_mu     0.107 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9789 
_exptl_absorpt_correction_T_max   0.9894 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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 Kappa CCD'
_diffrn_measurement_method        'Phi and omega scans to fill asym unit'
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             22344 
_diffrn_reflns_av_R_equivalents   0.0943 
_diffrn_reflns_av_sigmaI/netI     0.0678 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        20 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          2.99 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              3776 
_reflns_number_gt                 2464 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT' 
_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)+(0.0660P)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     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3776 
_refine_ls_number_parameters      294 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0881 
_refine_ls_R_factor_gt            0.0468 
_refine_ls_wR_factor_ref          0.1213 
_refine_ls_wR_factor_gt           0.1039 
_refine_ls_goodness_of_fit_ref    0.968 
_refine_ls_restrained_S_all       0.968 
_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 
C1 C 0.64201(18) -0.17195(16) -0.09885(14) 0.0398(7) Uani 1 1 d . . . 
H1A H 0.6582 -0.1263 -0.1294 0.060 Uiso 1 1 calc R . . 
H1B H 0.6150 -0.2117 -0.1324 0.060 Uiso 1 1 calc R . . 
H1C H 0.6991 -0.1922 -0.0742 0.060 Uiso 1 1 calc R . . 
C2 C 0.37613(15) -0.10563(14) 0.11419(14) 0.0303(6) Uani 1 1 d . . . 
H2A H 0.4015 -0.1113 0.1662 0.045 Uiso 1 1 calc R . . 
H2B H 0.3245 -0.1426 0.1065 0.045 Uiso 1 1 calc R . . 
H2C H 0.3522 -0.0529 0.1073 0.045 Uiso 1 1 calc R . . 
C3 C 0.68387(15) -0.05461(13) 0.00814(12) 0.0241(5) Uani 1 1 d . . . 
H3 H 0.7330 -0.0695 -0.0259 0.029 Uiso 1 1 calc R . . 
C4 C 0.59861(15) -0.09322(12) 0.00855(12) 0.0229(5) Uani 1 1 d . . . 
C5 C 0.52795(14) -0.07401(13) 0.06322(12) 0.0216(5) Uani 1 1 d . . . 
C6 C 0.54098(15) -0.01324(12) 0.11290(12) 0.0221(5) Uani 1 1 d . . . 
H6 H 0.4934 0.0003 0.1490 0.027 Uiso 1 1 calc R . . 
C7 C 0.62598(14) 0.02846(12) 0.10925(12) 0.0213(5) Uani 1 1 d . . . 
C8 C 0.69609(14) 0.00688(13) 0.05893(12) 0.0217(5) Uani 1 1 d . . . 
C9 C 0.64963(15) 0.10404(13) 0.14941(12) 0.0247(5) Uani 1 1 d . . . 
C10 C 0.62305(14) 0.11017(12) 0.23305(12) 0.0225(5) Uani 1 1 d . . . 
C11 C 0.59712(15) 0.18008(13) 0.26552(13) 0.0256(5) Uani 1 1 d . . . 
H11 H 0.5909 0.2245 0.2338 0.031 Uiso 1 1 calc R . . 
C12 C 0.58003(15) 0.18622(13) 0.34406(13) 0.0272(6) Uani 1 1 d . . . 
H12 H 0.5628 0.2347 0.3656 0.033 Uiso 1 1 calc R . . 
C13 C 0.58818(15) 0.12192(13) 0.39067(13) 0.0233(5) Uani 1 1 d . . . 
C14 C 0.61021(14) 0.05014(12) 0.35789(12) 0.0217(5) Uani 1 1 d . . . 
C15 C 0.62829(14) 0.04478(12) 0.28046(12) 0.0214(5) Uani 1 1 d . . . 
H15 H 0.6445 -0.0038 0.2588 0.026 Uiso 1 1 calc R . . 
C16 C 0.56758(19) 0.19574(14) 0.50509(14) 0.0379(6) Uani 1 1 d . . . 
H16A H 0.6222 0.2276 0.4910 0.057 Uiso 1 1 calc R . . 
H16B H 0.5662 0.1888 0.5609 0.057 Uiso 1 1 calc R . . 
H16C H 0.5094 0.2214 0.4884 0.057 Uiso 1 1 calc R . . 
C17 C 0.61220(16) -0.08651(13) 0.37473(14) 0.0289(6) Uani 1 1 d . . . 
H17A H 0.5592 -0.0914 0.3389 0.043 Uiso 1 1 calc R . . 
H17B H 0.6061 -0.1254 0.4153 0.043 Uiso 1 1 calc R . . 
H17C H 0.6718 -0.0945 0.3472 0.043 Uiso 1 1 calc R . . 
C18 C 0.78197(15) 0.05868(14) 0.06452(12) 0.0252(5) Uani 1 1 d . . . 
H18 H 0.7910 0.0902 0.0170 0.030 Uiso 1 1 calc R . . 
C19 C 0.87229(15) 0.01650(15) 0.08755(13) 0.0299(6) Uani 1 1 d . . . 
H19A H 0.8727 -0.0371 0.0676 0.036 Uiso 1 1 calc R . . 
H19B H 0.9289 0.0440 0.0684 0.036 Uiso 1 1 calc R . . 
C20 C 0.86890(15) 0.01719(15) 0.17322(14) 0.0301(6) Uani 1 1 d . . . 
C21 C 0.75950(15) 0.10949(13) 0.13452(13) 0.0253(5) Uani 1 1 d . . . 
C22 C 0.79376(16) 0.19237(15) 0.12539(14) 0.0327(6) Uani 1 1 d . . . 
C23 C 0.8184(3) 0.31081(19) 0.18704(19) 0.0857(13) Uani 1 1 d . . . 
H23A H 0.8855 0.3140 0.1734 0.129 Uiso 1 1 calc R . . 
H23B H 0.8082 0.3358 0.2368 0.129 Uiso 1 1 calc R . . 
H23C H 0.7806 0.3371 0.1478 0.129 Uiso 1 1 calc R . . 
O1 O 0.57426(10) -0.15109(9) -0.04120(8) 0.0273(4) Uani 1 1 d . . . 
O2 O 0.44936(10) -0.12026(8) 0.05952(9) 0.0269(4) Uani 1 1 d . . . 
O3 O 0.57492(11) 0.12166(9) 0.46847(9) 0.0286(4) Uani 1 1 d . . . 
O4 O 0.61159(11) -0.01140(8) 0.40791(8) 0.0273(4) Uani 1 1 d . . . 
O5 O 0.61233(10) 0.16826(8) 0.10705(8) 0.0286(4) Uani 1 1 d . . . 
H5 H 0.5533 0.1641 0.1039 0.043 Uiso 1 1 calc R . . 
O6 O 0.90999(12) -0.02292(11) 0.21872(10) 0.0440(5) Uani 1 1 d . . . 
O7 O 0.80936(10) 0.07378(9) 0.19827(8) 0.0285(4) Uani 1 1 d . . . 
O8 O 0.81918(13) 0.22016(10) 0.06579(10) 0.0472(5) Uani 1 1 d . . . 
O9 O 0.79043(14) 0.23086(10) 0.19160(10) 0.0491(5) 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 O1 1.435(3) . ? 
C2 O2 1.430(3) . ? 
C3 C4 1.379(3) . ? 
C3 C8 1.395(3) . ? 
C4 O1 1.369(3) . ? 
C4 C5 1.421(3) . ? 
C5 O2 1.372(2) . ? 
C5 C6 1.375(3) . ? 
C6 C7 1.404(3) . ? 
C7 C8 1.376(3) . ? 
C7 C9 1.520(3) . ? 
C8 C18 1.513(3) . ? 
C9 O5 1.435(3) . ? 
C9 C10 1.510(3) . ? 
C9 C21 1.579(3) . ? 
C10 C11 1.385(3) . ? 
C10 C15 1.403(3) . ? 
C11 C12 1.395(3) . ? 
C12 C13 1.382(3) . ? 
C13 O3 1.369(3) . ? 
C13 C14 1.402(3) . ? 
C14 O4 1.376(2) . ? 
C14 C15 1.377(3) . ? 
C16 O3 1.436(3) . ? 
C17 O4 1.422(3) . ? 
C18 C19 1.525(3) . ? 
C18 C21 1.537(3) . ? 
C19 C20 1.494(3) . ? 
C20 O6 1.204(3) . ? 
C20 O7 1.363(3) . ? 
C21 O7 1.454(3) . ? 
C21 C22 1.522(3) . ? 
C22 O8 1.200(3) . ? 
C22 O9 1.333(3) . ? 
C23 O9 1.441(3) . ? 
 
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 
C4 C3 C8 118.3(2) . . ? 
O1 C4 C3 124.8(2) . . ? 
O1 C4 C5 114.77(18) . . ? 
C3 C4 C5 120.4(2) . . ? 
O2 C5 C6 125.77(19) . . ? 
O2 C5 C4 113.74(18) . . ? 
C6 C5 C4 120.48(19) . . ? 
C5 C6 C7 118.6(2) . . ? 
C8 C7 C6 120.5(2) . . ? 
C8 C7 C9 111.61(18) . . ? 
C6 C7 C9 127.56(19) . . ? 
C7 C8 C3 121.49(19) . . ? 
C7 C8 C18 112.16(19) . . ? 
C3 C8 C18 126.31(19) . . ? 
O5 C9 C10 110.56(17) . . ? 
O5 C9 C7 110.37(17) . . ? 
C10 C9 C7 116.77(18) . . ? 
O5 C9 C21 103.37(16) . . ? 
C10 C9 C21 113.57(17) . . ? 
C7 C9 C21 101.09(17) . . ? 
C11 C10 C15 118.5(2) . . ? 
C11 C10 C9 121.5(2) . . ? 
C15 C10 C9 119.95(19) . . ? 
C10 C11 C12 120.9(2) . . ? 
C13 C12 C11 120.1(2) . . ? 
O3 C13 C12 125.0(2) . . ? 
O3 C13 C14 115.55(19) . . ? 
C12 C13 C14 119.5(2) . . ? 
O4 C14 C15 124.5(2) . . ? 
O4 C14 C13 115.47(18) . . ? 
C15 C14 C13 120.0(2) . . ? 
C14 C15 C10 120.9(2) . . ? 
C8 C18 C19 114.0(2) . . ? 
C8 C18 C21 102.93(17) . . ? 
C19 C18 C21 103.76(17) . . ? 
C20 C19 C18 103.43(19) . . ? 
O6 C20 O7 120.1(2) . . ? 
O6 C20 C19 129.7(2) . . ? 
O7 C20 C19 110.2(2) . . ? 
O7 C21 C22 109.00(17) . . ? 
O7 C21 C18 105.28(17) . . ? 
C22 C21 C18 112.95(19) . . ? 
O7 C21 C9 109.06(16) . . ? 
C22 C21 C9 112.77(18) . . ? 
C18 C21 C9 107.46(17) . . ? 
O8 C22 O9 124.1(2) . . ? 
O8 C22 C21 124.3(2) . . ? 
O9 C22 C21 111.6(2) . . ? 
C4 O1 C1 117.36(17) . . ? 
C5 O2 C2 116.92(16) . . ? 
C13 O3 C16 116.58(17) . . ? 
C14 O4 C17 116.69(16) . . ? 
C20 O7 C21 111.10(17) . . ? 
C22 O9 C23 114.9(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.258 
_refine_diff_density_min   -0.373 
_refine_diff_density_rms    0.053 
