 
data_01src401 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C21 H16 O9' 
_chemical_formula_weight          412.34 
 
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                    7.41810(10) 
_cell_length_b                    16.6837(3) 
_cell_length_c                    27.9934(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3464.50(10) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     7841 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.02 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.581 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1712 
_exptl_absorpt_coefficient_mu     0.126 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9875 
_exptl_absorpt_correction_T_max   0.9975 
_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             15941 
_diffrn_reflns_av_R_equivalents   0.1471 
_diffrn_reflns_av_sigmaI/netI     0.1296 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -25 
_diffrn_reflns_limit_l_max        33 
_diffrn_reflns_theta_min          2.91 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              3054 
_reflns_number_gt                 1651 
_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)+(0.0378P)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      SHELXL 
_refine_ls_extinction_coef        0.0008(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3054 
_refine_ls_number_parameters      273 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1285 
_refine_ls_R_factor_gt            0.0501 
_refine_ls_wR_factor_ref          0.1049 
_refine_ls_wR_factor_gt           0.0858 
_refine_ls_goodness_of_fit_ref    0.921 
_refine_ls_restrained_S_all       0.921 
_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 -0.2313(4) 0.06079(18) 0.30303(10) 0.0267(9) Uani 1 1 d . . . 
H1A H -0.2368 0.0198 0.3286 0.032 Uiso 1 1 calc R . . 
H1B H -0.3123 0.0441 0.2767 0.032 Uiso 1 1 calc R . . 
C2 C -0.1256(4) 0.17770(18) 0.32995(9) 0.0190(8) Uani 1 1 d . . . 
C3 C 0.0166(4) 0.13668(18) 0.30842(9) 0.0181(8) Uani 1 1 d . . . 
C4 C 0.1896(4) 0.16392(17) 0.30902(9) 0.0196(8) Uani 1 1 d . . . 
H4 H 0.2860 0.1350 0.2948 0.024 Uiso 1 1 calc R . . 
C5 C 0.2161(4) 0.23806(17) 0.33219(9) 0.0154(7) Uani 1 1 d . . . 
C6 C 0.0745(4) 0.27834(17) 0.35327(9) 0.0146(7) Uani 1 1 d . . . 
C7 C -0.1020(4) 0.24890(18) 0.35324(9) 0.0186(8) Uani 1 1 d . . . 
H7 H -0.1986 0.2764 0.3683 0.022 Uiso 1 1 calc R . . 
C8 C 0.3923(4) 0.28384(17) 0.33713(9) 0.0186(8) Uani 1 1 d . . . 
H8 H 0.4753 0.2583 0.3608 0.022 Uiso 1 1 calc R . . 
C9 C 0.3263(4) 0.36732(17) 0.35392(9) 0.0174(8) Uani 1 1 d . . . 
C10 C 0.1317(4) 0.35717(17) 0.37551(9) 0.0165(7) Uani 1 1 d . . . 
C11 C 0.1303(4) 0.35260(17) 0.42995(9) 0.0147(7) Uani 1 1 d . . . 
C12 C -0.0064(4) 0.39227(16) 0.45528(10) 0.0182(8) Uani 1 1 d . . . 
H12 H -0.0961 0.4229 0.4393 0.022 Uiso 1 1 calc R . . 
C13 C -0.0051(4) 0.38497(17) 0.50418(10) 0.0176(8) Uani 1 1 d . . . 
C14 C 0.1234(4) 0.34096(17) 0.52802(9) 0.0180(7) Uani 1 1 d . . . 
C15 C 0.2561(4) 0.30069(19) 0.50444(10) 0.0245(8) Uani 1 1 d . . . 
H15 H 0.3433 0.2696 0.5210 0.029 Uiso 1 1 calc R . . 
C16 C 0.2578(4) 0.30745(17) 0.45455(10) 0.0215(8) Uani 1 1 d . . . 
H16 H 0.3488 0.2803 0.4370 0.026 Uiso 1 1 calc R . . 
C17 C -0.0546(5) 0.39978(19) 0.58220(10) 0.0298(9) Uani 1 1 d . . . 
H17A H -0.1495 0.3778 0.6033 0.036 Uiso 1 1 calc R . . 
H17B H -0.0077 0.4497 0.5968 0.036 Uiso 1 1 calc R . . 
C18 C 0.4861(4) 0.30175(17) 0.29005(9) 0.0188(8) Uani 1 1 d . . . 
H18A H 0.6165 0.3114 0.2949 0.023 Uiso 1 1 calc R . . 
H18B H 0.4703 0.2571 0.2671 0.023 Uiso 1 1 calc R . . 
C19 C 0.3937(4) 0.37568(18) 0.27291(11) 0.0189(8) Uani 1 1 d . . . 
C20 C 0.4622(5) 0.4130(2) 0.38465(10) 0.0206(8) Uani 1 1 d . . . 
C21 C 0.5205(4) 0.53172(19) 0.42709(11) 0.0306(9) Uani 1 1 d . . . 
H21A H 0.4657 0.5839 0.4339 0.046 Uiso 1 1 calc R . . 
H21B H 0.6365 0.5397 0.4110 0.046 Uiso 1 1 calc R . . 
H21C H 0.5397 0.5026 0.4571 0.046 Uiso 1 1 calc R . . 
O1 O -0.2856(3) 0.13775(12) 0.32140(6) 0.0254(6) Uani 1 1 d . . . 
O2 O -0.0495(3) 0.06900(11) 0.28579(7) 0.0254(6) Uani 1 1 d . . . 
O3 O 0.0172(3) 0.42108(11) 0.36207(6) 0.0194(5) Uani 1 1 d . . . 
H3 H -0.0045 0.4182 0.3327 0.029 Uiso 1 1 calc R . . 
O4 O -0.1274(3) 0.41632(12) 0.53597(6) 0.0283(6) Uani 1 1 d . . . 
O5 O 0.0888(3) 0.34242(12) 0.57666(6) 0.0259(6) Uani 1 1 d . . . 
O6 O 0.3076(3) 0.41275(11) 0.30952(6) 0.0204(5) Uani 1 1 d . . . 
O7 O 0.6049(3) 0.38612(13) 0.39674(7) 0.0349(6) Uani 1 1 d . . . 
O8 O 0.4016(3) 0.48573(12) 0.39637(6) 0.0258(6) Uani 1 1 d . . . 
O9 O 0.3886(3) 0.40399(11) 0.23340(7) 0.0250(6) 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 O2 1.439(3) . ? 
C1 O1 1.441(3) . ? 
C2 C7 1.366(4) . ? 
C2 O1 1.382(3) . ? 
C2 C3 1.394(4) . ? 
C3 C4 1.362(4) . ? 
C3 O2 1.385(3) . ? 
C4 C5 1.410(4) . ? 
C5 C6 1.379(4) . ? 
C5 C8 1.520(4) . ? 
C6 C7 1.398(4) . ? 
C6 C10 1.516(4) . ? 
C8 C18 1.520(4) . ? 
C8 C9 1.549(4) . ? 
C9 O6 1.462(3) . ? 
C9 C20 1.529(4) . ? 
C9 C10 1.574(4) . ? 
C10 O3 1.414(3) . ? 
C10 C11 1.526(4) . ? 
C11 C16 1.391(4) . ? 
C11 C12 1.403(4) . ? 
C12 C13 1.374(4) . ? 
C13 O4 1.375(3) . ? 
C13 C14 1.376(4) . ? 
C14 C15 1.362(4) . ? 
C14 O5 1.386(3) . ? 
C15 C16 1.401(3) . ? 
C17 O4 1.429(3) . ? 
C17 O5 1.439(3) . ? 
C18 C19 1.490(4) . ? 
C19 O9 1.203(3) . ? 
C19 O6 1.357(3) . ? 
C20 O7 1.198(3) . ? 
C20 O8 1.335(3) . ? 
C21 O8 1.452(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 
O2 C1 O1 107.3(2) . . ? 
C7 C2 O1 127.7(3) . . ? 
C7 C2 C3 122.4(3) . . ? 
O1 C2 C3 109.8(3) . . ? 
C4 C3 O2 127.7(3) . . ? 
C4 C3 C2 123.0(3) . . ? 
O2 C3 C2 109.3(3) . . ? 
C3 C4 C5 115.4(3) . . ? 
C6 C5 C4 121.2(3) . . ? 
C6 C5 C8 111.8(2) . . ? 
C4 C5 C8 127.0(3) . . ? 
C5 C6 C7 122.8(3) . . ? 
C5 C6 C10 112.7(3) . . ? 
C7 C6 C10 124.6(3) . . ? 
C2 C7 C6 115.2(3) . . ? 
C18 C8 C5 114.4(2) . . ? 
C18 C8 C9 103.3(2) . . ? 
C5 C8 C9 102.0(2) . . ? 
O6 C9 C20 106.4(2) . . ? 
O6 C9 C8 103.78(19) . . ? 
C20 C9 C8 114.2(3) . . ? 
O6 C9 C10 107.2(2) . . ? 
C20 C9 C10 116.3(2) . . ? 
C8 C9 C10 108.0(2) . . ? 
O3 C10 C6 112.1(2) . . ? 
O3 C10 C11 107.4(2) . . ? 
C6 C10 C11 111.4(2) . . ? 
O3 C10 C9 111.6(2) . . ? 
C6 C10 C9 101.1(2) . . ? 
C11 C10 C9 113.3(2) . . ? 
C16 C11 C12 119.8(2) . . ? 
C16 C11 C10 121.1(3) . . ? 
C12 C11 C10 119.1(3) . . ? 
C13 C12 C11 117.1(3) . . ? 
C12 C13 O4 127.3(3) . . ? 
C12 C13 C14 122.4(3) . . ? 
O4 C13 C14 110.3(2) . . ? 
C15 C14 C13 121.9(3) . . ? 
C15 C14 O5 128.2(3) . . ? 
C13 C14 O5 109.8(3) . . ? 
C14 C15 C16 116.7(3) . . ? 
C11 C16 C15 122.1(3) . . ? 
O4 C17 O5 108.1(2) . . ? 
C19 C18 C8 103.4(2) . . ? 
O9 C19 O6 120.1(3) . . ? 
O9 C19 C18 129.4(3) . . ? 
O6 C19 C18 110.5(2) . . ? 
O7 C20 O8 124.6(3) . . ? 
O7 C20 C9 123.7(3) . . ? 
O8 C20 C9 111.7(3) . . ? 
C2 O1 C1 104.6(2) . . ? 
C3 O2 C1 104.8(2) . . ? 
C13 O4 C17 105.3(2) . . ? 
C14 O5 C17 104.7(2) . . ? 
C19 O6 C9 111.2(2) . . ? 
C20 O8 C21 114.9(2) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O3 H3 O9  0.84 2.03 2.852(3) 167.4 6_556 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.03 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.282 
_refine_diff_density_min   -0.336 
_refine_diff_density_rms    0.083 
