data_wgser 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C13 H14 O5' 
_chemical_formula_weight          250.24 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1) 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    8.9778(8) 
_cell_length_b                    5.9703(8) 
_cell_length_c                    12.6038(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  107.981(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      642.57(12) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     521 
_cell_measurement_theta_min       5.18 
_cell_measurement_theta_max       47.77 
  
_exptl_crystal_description        fiber 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.45 
_exptl_crystal_size_mid           0.08 
_exptl_crystal_size_min           0.03 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.293 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              264 
_exptl_absorpt_coefficient_mu     0.840 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   0.7038 
_exptl_absorpt_correction_T_max   0.9752 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_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             1234 
_diffrn_reflns_av_R_equivalents   0.0278 
_diffrn_reflns_av_sigmaI/netI     0.0541 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -6 
_diffrn_reflns_limit_k_max        3 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          5.18 
_diffrn_reflns_theta_max          59.33 
_reflns_number_total              925 
_reflns_number_gt                 768 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_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^ > 2sigma(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^)+(0.0200P)^2^+0.0000P] 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     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0054(8) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.2(4) 
_refine_ls_number_reflns          925 
_refine_ls_number_parameters      165 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0434 
_refine_ls_R_factor_gt            0.0363 
_refine_ls_wR_factor_ref          0.0659 
_refine_ls_wR_factor_gt           0.0633 
_refine_ls_goodness_of_fit_ref    1.023 
_refine_ls_restrained_S_all       1.022 
_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 0.7369(4) 0.5177(10) 0.9550(3) 0.0370(14) Uani 1 1 d . . . 
H1 H 0.6559 0.4281 0.9757 0.044 Uiso 1 1 calc R . . 
C2 C 0.6671(5) 0.8692(10) 1.0132(4) 0.0331(14) Uani 1 1 d . . . 
C3 C 0.7392(4) 0.7734(9) 1.1292(4) 0.0356(15) Uani 1 1 d . . . 
H3 H 0.6641 0.6647 1.1452 0.043 Uiso 1 1 calc R . . 
C4 C 0.8854(5) 0.5145(10) 1.0536(4) 0.0396(15) Uani 1 1 d . . . 
C5 C 0.7601(4) 0.4129(10) 0.8527(4) 0.0544(17) Uani 1 1 d . . . 
H5A H 0.8208 0.5144 0.8195 0.065 Uiso 1 1 calc R . . 
H5B H 0.8177 0.2697 0.8721 0.065 Uiso 1 1 calc R . . 
C6 C 0.6146(5) 0.2312(11) 0.6882(4) 0.075(2) Uani 1 1 d . . . 
H6A H 0.6755 0.0952 0.7195 0.090 Uiso 1 1 calc R . . 
H6B H 0.6677 0.3083 0.6404 0.090 Uiso 1 1 calc R . . 
C7 C 0.4503(5) 0.1666(11) 0.6197(4) 0.0472(16) Uani 1 1 d . . . 
C8 C 0.3638(6) 0.3032(10) 0.5358(4) 0.0599(19) Uani 1 1 d . . . 
H8 H 0.4070 0.4409 0.5214 0.072 Uiso 1 1 calc R . . 
C9 C 0.2127(7) 0.2420(13) 0.4712(5) 0.0682(19) Uani 1 1 d . . . 
H9 H 0.1543 0.3357 0.4120 0.082 Uiso 1 1 calc R . . 
C10 C 0.1499(6) 0.0464(13) 0.4939(4) 0.0615(19) Uani 1 1 d . . . 
H10 H 0.0467 0.0046 0.4511 0.074 Uiso 1 1 calc R . . 
C11 C 0.2356(5) -0.0903(11) 0.5786(4) 0.0613(17) Uani 1 1 d . . . 
H11 H 0.1920 -0.2270 0.5939 0.074 Uiso 1 1 calc R . . 
C12 C 0.3859(5) -0.0283(11) 0.6419(4) 0.0538(17) Uani 1 1 d . . . 
H12 H 0.4444 -0.1222 0.7009 0.065 Uiso 1 1 calc R . . 
C13 C 0.7780(5) 0.9514(10) 1.2180(4) 0.060(2) Uani 1 1 d . . . 
H13A H 0.8218 0.8813 1.2914 0.089 Uiso 1 1 calc R . . 
H13B H 0.6827 1.0338 1.2157 0.089 Uiso 1 1 calc R . . 
H13C H 0.8550 1.0552 1.2047 0.089 Uiso 1 1 calc R . . 
O1 O 0.6758(3) 0.7436(6) 0.9278(2) 0.0323(9) Uani 1 1 d . . . 
O2 O 0.8854(3) 0.6567(6) 1.1369(2) 0.0403(10) Uani 1 1 d . . . 
O3 O 0.6004(3) 1.0480(6) 0.9948(3) 0.0472(11) Uani 1 1 d . . . 
O4 O 0.9962(3) 0.3957(6) 1.0615(2) 0.0584(12) Uani 1 1 d . . . 
O5 O 0.6073(3) 0.3747(7) 0.7756(3) 0.0515(11) Uani 1 1 d . . . 
  
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 
C1 0.023(2) 0.039(4) 0.042(3) -0.008(3) 0.000(2) -0.003(2) 
C2 0.028(2) 0.033(5) 0.042(3) -0.003(3) 0.016(2) -0.008(3) 
C3 0.026(2) 0.048(4) 0.037(3) 0.003(3) 0.016(2) 0.004(2) 
C4 0.035(3) 0.037(4) 0.046(3) 0.007(3) 0.011(3) 0.003(3) 
C5 0.031(2) 0.067(5) 0.061(3) -0.025(4) 0.009(2) -0.001(3) 
C6 0.050(3) 0.107(7) 0.075(4) -0.045(4) 0.027(3) -0.023(3) 
C7 0.045(3) 0.052(6) 0.049(4) -0.015(4) 0.021(3) -0.006(3) 
C8 0.074(4) 0.046(6) 0.073(4) 0.004(4) 0.042(3) -0.004(4) 
C9 0.077(4) 0.071(6) 0.055(4) 0.017(4) 0.017(3) 0.018(4) 
C10 0.052(3) 0.072(6) 0.051(4) -0.001(4) 0.004(3) -0.001(4) 
C11 0.057(3) 0.044(5) 0.076(4) 0.003(4) 0.011(3) -0.010(3) 
C12 0.047(3) 0.058(6) 0.052(3) 0.005(3) 0.008(3) 0.003(3) 
C13 0.048(3) 0.076(6) 0.055(3) -0.029(4) 0.016(3) -0.007(3) 
O1 0.0305(15) 0.028(3) 0.0376(19) 0.0055(18) 0.0095(14) 0.0056(16) 
O2 0.0279(16) 0.047(3) 0.0433(19) 0.001(2) 0.0068(14) 0.0025(17) 
O3 0.0407(19) 0.031(3) 0.070(3) 0.004(2) 0.0174(17) 0.0040(19) 
O4 0.0350(16) 0.048(3) 0.083(3) -0.001(3) 0.0043(18) 0.017(2) 
O5 0.0368(17) 0.062(3) 0.053(2) -0.019(2) 0.0099(15) -0.0022(19) 
  
_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 1.457(5) . ? 
C1 C5 1.505(5) . ? 
C1 C4 1.516(5) . ? 
C2 O3 1.211(5) . ? 
C2 O1 1.333(5) . ? 
C2 C3 1.517(6) . ? 
C3 O2 1.463(4) . ? 
C3 C13 1.504(6) . ? 
C4 O4 1.201(5) . ? 
C4 O2 1.350(5) . ? 
C5 O5 1.434(4) . ? 
C6 O5 1.413(5) . ? 
C6 C7 1.511(6) . ? 
C7 C12 1.366(7) . ? 
C7 C8 1.371(6) . ? 
C8 C9 1.399(7) . ? 
C9 C10 1.365(8) . ? 
C10 C11 1.375(7) . ? 
C11 C12 1.390(6) . ? 
  
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 
O1 C1 C5 109.0(4) . . ? 
O1 C1 C4 112.1(4) . . ? 
C5 C1 C4 112.2(4) . . ? 
O3 C2 O1 119.4(5) . . ? 
O3 C2 C3 123.7(5) . . ? 
O1 C2 C3 116.9(5) . . ? 
O2 C3 C13 106.9(3) . . ? 
O2 C3 C2 110.5(3) . . ? 
C13 C3 C2 112.5(5) . . ? 
O4 C4 O2 120.4(4) . . ? 
O4 C4 C1 124.9(5) . . ? 
O2 C4 C1 114.7(4) . . ? 
O5 C5 C1 106.9(3) . . ? 
O5 C6 C7 109.1(4) . . ? 
C12 C7 C8 119.3(5) . . ? 
C12 C7 C6 120.0(6) . . ? 
C8 C7 C6 120.6(6) . . ? 
C7 C8 C9 120.7(6) . . ? 
C10 C9 C8 119.4(6) . . ? 
C9 C10 C11 120.2(5) . . ? 
C10 C11 C12 120.0(6) . . ? 
C7 C12 C11 120.5(6) . . ? 
C2 O1 C1 116.2(4) . . ? 
C4 O2 C3 117.6(3) . . ? 
C6 O5 C5 111.1(3) . . ? 
  
_diffrn_measured_fraction_theta_max    0.697 
_diffrn_reflns_theta_full              59.33 
_diffrn_measured_fraction_theta_full   0.697 
_refine_diff_density_max    0.114 
_refine_diff_density_min   -0.147 
_refine_diff_density_rms    0.032