data_theod44 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C19 H24 O5' 
_chemical_formula_weight          332.38 
  
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            Orthorhombic 
_symmetry_space_group_name_H-M    Pbca 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 '-x+1/2, -y, z+1/2' 
 '-x, -y, -z' 
 '-x-1/2, y-1/2, z' 
 'x, -y-1/2, z-1/2' 
 'x-1/2, y, -z-1/2' 
  
_cell_length_a                    10.1514(5) 
_cell_length_b                    18.0417(11) 
_cell_length_c                    18.4086(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3371.5(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     8575 
_cell_measurement_theta_min       4.80 
_cell_measurement_theta_max       64.37 
  
_exptl_crystal_description        Plate 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.17 
_exptl_crystal_size_mid           0.11 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_diffrn     1.310 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1424 
_exptl_absorpt_coefficient_mu     0.770 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.8803 
_exptl_absorpt_correction_T_max   0.9625 
_exptl_absorpt_process_details    SADABS 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       100(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   'Bruker APEX-II CCD' 
_diffrn_measurement_method        '\f and \w scans' 
_diffrn_reflns_number             16988 
_diffrn_reflns_av_R_equivalents   0.0367 
_diffrn_reflns_av_sigmaI/netI     0.0227 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          4.80 
_diffrn_reflns_theta_max          64.83 
_reflns_number_total              2800 
_reflns_number_gt                 2379 
_reflns_threshold_expression      >2\s(I) 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_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^ > 2\s(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^)+(0.0426P)^2^+0.9599P] 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     constr 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.00027(6) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          2800 
_refine_ls_number_parameters      222 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0397 
_refine_ls_R_factor_gt            0.0313 
_refine_ls_wR_factor_ref          0.0831 
_refine_ls_wR_factor_gt           0.0783 
_refine_ls_goodness_of_fit_ref    1.046 
_refine_ls_restrained_S_all       1.046 
_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 
O1 O 0.54487(10) 0.23811(6) 0.87129(5) 0.0279(3) Uani 1 1 d . . . 
O2 O 0.58565(9) 0.18202(5) 0.76549(5) 0.0221(2) Uani 1 1 d . . . 
O3 O 0.56277(9) 0.20570(6) 0.51318(5) 0.0210(2) Uani 1 1 d . . . 
H3O H 0.5909 0.2186 0.4722 0.032 Uiso 1 1 calc R . . 
O4 O 0.79319(9) 0.27280(6) 0.47532(5) 0.0222(2) Uani 1 1 d . . . 
H4O H 0.8751 0.2787 0.4720 0.033 Uiso 1 1 calc R . . 
O5 O 0.71911(9) 0.38079(5) 0.63017(5) 0.0198(2) Uani 1 1 d . . . 
C1 C 0.61343(13) 0.23298(8) 0.81770(7) 0.0201(3) Uani 1 1 d . . . 
C2 C 0.72970(13) 0.27630(8) 0.79584(7) 0.0186(3) Uani 1 1 d . . . 
C3 C 0.76827(13) 0.24989(8) 0.73199(7) 0.0187(3) Uani 1 1 d . . . 
H3 H 0.8433 0.2670 0.7061 0.022 Uiso 1 1 calc R . . 
C4 C 0.67895(13) 0.19008(8) 0.70607(7) 0.0191(3) Uani 1 1 d . . . 
H4 H 0.7295 0.1430 0.6992 0.023 Uiso 1 1 calc R . . 
C5 C 0.59865(13) 0.20736(8) 0.63805(7) 0.0193(3) Uani 1 1 d . . . 
H5A H 0.5590 0.2571 0.6444 0.023 Uiso 1 1 calc R . . 
H5B H 0.5252 0.1713 0.6356 0.023 Uiso 1 1 calc R . . 
C6 C 0.66946(13) 0.20636(8) 0.56457(7) 0.0186(3) Uani 1 1 d . . . 
C7 C 0.75515(13) 0.27574(8) 0.54998(7) 0.0184(3) Uani 1 1 d . . . 
H7 H 0.8361 0.2729 0.5808 0.022 Uiso 1 1 calc R . . 
C8 C 0.68617(13) 0.34725(8) 0.56544(7) 0.0187(3) Uani 1 1 d . . . 
C9 C 0.59314(14) 0.38751(8) 0.53142(8) 0.0237(3) Uani 1 1 d . . . 
H9 H 0.5535 0.3768 0.4859 0.028 Uiso 1 1 calc R . . 
C10 C 0.56566(14) 0.44973(8) 0.57743(8) 0.0242(3) Uani 1 1 d . . . 
H10 H 0.5038 0.4881 0.5681 0.029 Uiso 1 1 calc R . . 
C11 C 0.64350(14) 0.44385(8) 0.63631(8) 0.0205(3) Uani 1 1 d . . . 
C12 C 0.66233(14) 0.48993(8) 0.70251(8) 0.0224(3) Uani 1 1 d . . . 
H12A H 0.5924 0.5282 0.7040 0.027 Uiso 1 1 calc R . . 
H12B H 0.7480 0.5159 0.6988 0.027 Uiso 1 1 calc R . . 
C13 C 0.65923(13) 0.44568(8) 0.77464(7) 0.0197(3) Uani 1 1 d . . . 
H13 H 0.5934 0.4049 0.7690 0.024 Uiso 1 1 calc R . . 
C14 C 0.79408(13) 0.40976(8) 0.79081(8) 0.0209(3) Uani 1 1 d . . . 
H14A H 0.8369 0.3961 0.7444 0.025 Uiso 1 1 calc R . . 
H14B H 0.8512 0.4464 0.8156 0.025 Uiso 1 1 calc R . . 
C15 C 0.78165(14) 0.34084(8) 0.83839(8) 0.0224(3) Uani 1 1 d . . . 
H15A H 0.8691 0.3281 0.8587 0.027 Uiso 1 1 calc R . . 
H15B H 0.7215 0.3514 0.8794 0.027 Uiso 1 1 calc R . . 
C16 C 0.75189(14) 0.13628(8) 0.55508(8) 0.0223(3) Uani 1 1 d . . . 
H16A H 0.6975 0.0927 0.5655 0.033 Uiso 1 1 calc R . . 
H16B H 0.8268 0.1376 0.5886 0.033 Uiso 1 1 calc R . . 
H16C H 0.7843 0.1335 0.5050 0.033 Uiso 1 1 calc R . . 
C17 C 0.61699(14) 0.49270(8) 0.83880(8) 0.0230(3) Uani 1 1 d . . . 
C18 C 0.52521(16) 0.46951(10) 0.88454(8) 0.0320(4) Uani 1 1 d . . . 
H18A H 0.5023 0.4989 0.9254 0.038 Uiso 1 1 calc R . . 
H18B H 0.4823 0.4235 0.8765 0.038 Uiso 1 1 calc R . . 
C19 C 0.68747(17) 0.56530(9) 0.84956(9) 0.0318(4) Uani 1 1 d . . . 
H19A H 0.6595 0.6005 0.8120 0.048 Uiso 1 1 calc R . . 
H19B H 0.7828 0.5574 0.8460 0.048 Uiso 1 1 calc R . . 
H19C H 0.6660 0.5853 0.8976 0.048 Uiso 1 1 calc R . . 
  
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 
O1 0.0176(5) 0.0504(7) 0.0156(5) -0.0022(5) 0.0022(4) 0.0011(5) 
O2 0.0218(5) 0.0300(5) 0.0146(5) 0.0007(4) 0.0025(4) -0.0043(4) 
O3 0.0149(5) 0.0347(6) 0.0135(5) 0.0010(4) -0.0016(4) -0.0023(4) 
O4 0.0157(5) 0.0372(6) 0.0139(5) -0.0006(4) 0.0032(4) -0.0023(4) 
O5 0.0191(5) 0.0231(5) 0.0173(5) -0.0007(4) -0.0016(4) 0.0016(4) 
C1 0.0170(7) 0.0287(8) 0.0146(7) 0.0003(6) -0.0027(6) 0.0046(6) 
C2 0.0167(7) 0.0225(7) 0.0165(7) 0.0026(5) -0.0015(6) 0.0047(5) 
C3 0.0151(7) 0.0246(7) 0.0164(7) 0.0041(5) -0.0007(5) 0.0029(6) 
C4 0.0186(7) 0.0249(7) 0.0137(7) 0.0013(5) 0.0040(6) 0.0021(6) 
C5 0.0163(7) 0.0258(7) 0.0158(7) -0.0001(5) 0.0017(6) -0.0012(6) 
C6 0.0151(7) 0.0271(7) 0.0137(7) -0.0007(5) -0.0022(5) 0.0002(6) 
C7 0.0144(6) 0.0290(7) 0.0120(6) -0.0003(5) -0.0004(6) -0.0006(5) 
C8 0.0166(6) 0.0267(7) 0.0128(6) 0.0009(6) 0.0009(5) -0.0040(6) 
C9 0.0237(7) 0.0310(8) 0.0164(7) 0.0018(6) -0.0034(6) 0.0012(6) 
C10 0.0244(7) 0.0262(7) 0.0221(7) 0.0040(6) -0.0007(6) 0.0052(6) 
C11 0.0214(7) 0.0198(7) 0.0204(7) 0.0030(5) 0.0029(6) 0.0015(6) 
C12 0.0245(7) 0.0221(7) 0.0207(7) 0.0019(6) -0.0001(6) 0.0017(6) 
C13 0.0179(7) 0.0225(7) 0.0187(7) 0.0000(6) -0.0014(6) -0.0009(6) 
C14 0.0182(7) 0.0249(7) 0.0196(7) -0.0028(6) -0.0008(6) -0.0001(6) 
C15 0.0217(7) 0.0276(8) 0.0179(7) -0.0016(6) -0.0034(6) 0.0043(6) 
C16 0.0215(7) 0.0271(7) 0.0181(7) -0.0015(6) 0.0014(6) 0.0017(6) 
C17 0.0200(7) 0.0290(8) 0.0201(7) 0.0003(6) -0.0033(6) 0.0053(6) 
C18 0.0288(8) 0.0427(9) 0.0244(8) -0.0012(7) 0.0035(7) 0.0053(7) 
C19 0.0349(9) 0.0293(8) 0.0313(8) -0.0085(7) 0.0017(7) 0.0043(7) 
  
_geom_special_details 
; 
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell s.u.'s are taken 
 into account individually in the estimation of s.u.'s in distances, angles 
 and torsion angles; correlations between s.u.'s in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell s.u.'s is used for estimating s.u.'s 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 
O1 C1 1.2108(17) . ? 
O2 C1 1.3596(17) . ? 
O2 C4 1.4542(16) . ? 
O3 C6 1.4381(16) . ? 
O3 H3O 0.8400 . ? 
O4 C7 1.4286(16) . ? 
O4 H4O 0.8400 . ? 
O5 C11 1.3772(17) . ? 
O5 C8 1.3775(16) . ? 
C1 C2 1.472(2) . ? 
C2 C3 1.327(2) . ? 
C2 C15 1.499(2) . ? 
C3 C4 1.488(2) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.5261(19) . ? 
C4 H4 1.0000 . ? 
C5 C6 1.5319(18) . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 C16 1.526(2) . ? 
C6 C7 1.5478(19) . ? 
C7 C8 1.4953(19) . ? 
C7 H7 1.0000 . ? 
C8 C9 1.346(2) . ? 
C9 C10 1.434(2) . ? 
C9 H9 0.9500 . ? 
C10 C11 1.346(2) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.488(2) . ? 
C12 C13 1.5495(19) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C13 C17 1.5161(19) . ? 
C13 C14 1.5435(19) . ? 
C13 H13 1.0000 . ? 
C14 C15 1.5261(19) . ? 
C14 H14A 0.9900 . ? 
C14 H14B 0.9900 . ? 
C15 H15A 0.9900 . ? 
C15 H15B 0.9900 . ? 
C16 H16A 0.9800 . ? 
C16 H16B 0.9800 . ? 
C16 H16C 0.9800 . ? 
C17 C18 1.324(2) . ? 
C17 C19 1.506(2) . ? 
C18 H18A 0.9500 . ? 
C18 H18B 0.9500 . ? 
C19 H19A 0.9800 . ? 
C19 H19B 0.9800 . ? 
C19 H19C 0.9800 . ? 
  
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 
C1 O2 C4 109.21(10) . . ? 
C6 O3 H3O 109.5 . . ? 
C7 O4 H4O 109.5 . . ? 
C11 O5 C8 107.38(11) . . ? 
O1 C1 O2 120.56(13) . . ? 
O1 C1 C2 130.02(13) . . ? 
O2 C1 C2 109.40(11) . . ? 
C3 C2 C1 106.74(12) . . ? 
C3 C2 C15 129.62(13) . . ? 
C1 C2 C15 123.49(12) . . ? 
C2 C3 C4 111.38(12) . . ? 
C2 C3 H3 124.3 . . ? 
C4 C3 H3 124.3 . . ? 
O2 C4 C3 103.19(11) . . ? 
O2 C4 C5 106.84(10) . . ? 
C3 C4 C5 116.13(11) . . ? 
O2 C4 H4 110.1 . . ? 
C3 C4 H4 110.1 . . ? 
C5 C4 H4 110.1 . . ? 
C4 C5 C6 118.13(11) . . ? 
C4 C5 H5A 107.8 . . ? 
C6 C5 H5A 107.8 . . ? 
C4 C5 H5B 107.8 . . ? 
C6 C5 H5B 107.8 . . ? 
H5A C5 H5B 107.1 . . ? 
O3 C6 C16 109.31(11) . . ? 
O3 C6 C5 103.16(10) . . ? 
C16 C6 C5 111.60(11) . . ? 
O3 C6 C7 108.41(11) . . ? 
C16 C6 C7 109.99(11) . . ? 
C5 C6 C7 114.05(11) . . ? 
O4 C7 C8 109.99(11) . . ? 
O4 C7 C6 106.79(11) . . ? 
C8 C7 C6 113.67(11) . . ? 
O4 C7 H7 108.8 . . ? 
C8 C7 H7 108.8 . . ? 
C6 C7 H7 108.8 . . ? 
C9 C8 O5 109.61(12) . . ? 
C9 C8 C7 134.88(13) . . ? 
O5 C8 C7 115.47(11) . . ? 
C8 C9 C10 106.51(12) . . ? 
C8 C9 H9 126.7 . . ? 
C10 C9 H9 126.7 . . ? 
C11 C10 C9 107.46(13) . . ? 
C11 C10 H10 126.3 . . ? 
C9 C10 H10 126.3 . . ? 
C10 C11 O5 109.04(12) . . ? 
C10 C11 C12 133.74(13) . . ? 
O5 C11 C12 117.22(12) . . ? 
C11 C12 C13 114.30(11) . . ? 
C11 C12 H12A 108.7 . . ? 
C13 C12 H12A 108.7 . . ? 
C11 C12 H12B 108.7 . . ? 
C13 C12 H12B 108.7 . . ? 
H12A C12 H12B 107.6 . . ? 
C17 C13 C14 109.60(11) . . ? 
C17 C13 C12 112.65(11) . . ? 
C14 C13 C12 111.32(11) . . ? 
C17 C13 H13 107.7 . . ? 
C14 C13 H13 107.7 . . ? 
C12 C13 H13 107.7 . . ? 
C15 C14 C13 112.30(11) . . ? 
C15 C14 H14A 109.1 . . ? 
C13 C14 H14A 109.1 . . ? 
C15 C14 H14B 109.1 . . ? 
C13 C14 H14B 109.1 . . ? 
H14A C14 H14B 107.9 . . ? 
C2 C15 C14 111.23(11) . . ? 
C2 C15 H15A 109.4 . . ? 
C14 C15 H15A 109.4 . . ? 
C2 C15 H15B 109.4 . . ? 
C14 C15 H15B 109.4 . . ? 
H15A C15 H15B 108.0 . . ? 
C6 C16 H16A 109.5 . . ? 
C6 C16 H16B 109.5 . . ? 
H16A C16 H16B 109.5 . . ? 
C6 C16 H16C 109.5 . . ? 
H16A C16 H16C 109.5 . . ? 
H16B C16 H16C 109.5 . . ? 
C18 C17 C19 121.72(15) . . ? 
C18 C17 C13 121.19(14) . . ? 
C19 C17 C13 117.05(13) . . ? 
C17 C18 H18A 120.0 . . ? 
C17 C18 H18B 120.0 . . ? 
H18A C18 H18B 120.0 . . ? 
C17 C19 H19A 109.5 . . ? 
C17 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
C17 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
  
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 H3O O4  0.84 2.28 2.7244(13) 113.7 . 
O3 H3O O1  0.84 2.07 2.8077(14) 146.6 7_565 
O4 H4O O3  0.84 1.95 2.7721(13) 167.7 2_556 
  
_diffrn_measured_fraction_theta_max    0.980 
_diffrn_reflns_theta_full              64.83 
_diffrn_measured_fraction_theta_full   0.980 
_refine_diff_density_max    0.240 
_refine_diff_density_min   -0.176 
_refine_diff_density_rms    0.036