data_baran116 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C25 H34 O7' 
_chemical_formula_weight          446.52 
  
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            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                    9.789(2) 
_cell_length_b                    7.7354(17) 
_cell_length_c                    15.707(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  107.521(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1134.2(4) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     4987 
_cell_measurement_theta_min       2.72 
_cell_measurement_theta_max       25.56 
  
_exptl_crystal_description        blade 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.57 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.308 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              480 
_exptl_absorpt_coefficient_mu     0.095 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9481 
_exptl_absorpt_correction_T_max   0.9813 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       123(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   'Bruker APEX-II CCD' 
_diffrn_measurement_method        '\f and \w scans' 
_diffrn_reflns_number             7334 
_diffrn_reflns_av_R_equivalents   0.0439 
_diffrn_reflns_av_sigmaI/netI     0.0642 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.18 
_diffrn_reflns_theta_max          25.56 
_reflns_number_total              3878 
_reflns_number_gt                 3603 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_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^)+(0.0438P)^2^+0.3502P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.2(10) 
_refine_ls_number_reflns          3878 
_refine_ls_number_parameters      289 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0506 
_refine_ls_R_factor_gt            0.0469 
_refine_ls_wR_factor_ref          0.1187 
_refine_ls_wR_factor_gt           0.1148 
_refine_ls_goodness_of_fit_ref    1.125 
_refine_ls_restrained_S_all       1.125 
_refine_ls_shift/su_max           0.003 
_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 0.41786(19) 0.6224(2) 0.40769(11) 0.0183(4) Uani 1 1 d . . . 
O2 O 0.4254(2) 0.8582(2) 0.32214(11) 0.0201(4) Uani 1 1 d . . . 
O3 O 0.66712(18) 0.2548(2) 0.34563(10) 0.0150(4) Uani 1 1 d . . . 
O4 O 0.87049(18) 0.3984(2) 0.40287(11) 0.0193(4) Uani 1 1 d . . . 
O5 O 0.9658(2) 0.6283(3) 0.35238(13) 0.0263(4) Uani 1 1 d . . . 
O6 O 0.79276(19) -0.2138(2) 0.09971(12) 0.0198(4) Uani 1 1 d . . . 
O7 O 0.9636(2) -0.0594(2) 0.06048(14) 0.0286(5) Uani 1 1 d . . . 
C1 C 0.3953(6) 0.7705(5) 0.4545(2) 0.0584(12) Uani 1 1 d . . . 
H1A H 0.4615 0.7700 0.5162 0.070 Uiso 1 1 calc R . . 
H1B H 0.2957 0.7726 0.4574 0.070 Uiso 1 1 calc R . . 
C2 C 0.4217(5) 0.9174(4) 0.4068(2) 0.0453(10) Uani 1 1 d . . . 
H2A H 0.3446 1.0040 0.3997 0.054 Uiso 1 1 calc R . . 
H2B H 0.5141 0.9716 0.4396 0.054 Uiso 1 1 calc R . . 
C3 C 0.3973(3) 0.6768(3) 0.31796(17) 0.0172(5) Uani 1 1 d . . . 
C4 C 0.2431(3) 0.6356(4) 0.25892(17) 0.0207(6) Uani 1 1 d . . . 
H4A H 0.2080 0.7264 0.2132 0.025 Uiso 1 1 calc R . . 
H4B H 0.1772 0.6281 0.2958 0.025 Uiso 1 1 calc R . . 
C5 C 0.2524(3) 0.4591(3) 0.21422(18) 0.0204(6) Uani 1 1 d . . . 
H5A H 0.1853 0.3746 0.2271 0.024 Uiso 1 1 calc R . . 
H5B H 0.2295 0.4721 0.1487 0.024 Uiso 1 1 calc R . . 
C6 C 0.4086(3) 0.4007(3) 0.25570(16) 0.0155(5) Uani 1 1 d . . . 
H6A H 0.4171 0.3434 0.3141 0.019 Uiso 1 1 calc R . . 
C7 C 0.4907(3) 0.6720(3) 0.18781(16) 0.0178(5) Uani 1 1 d . . . 
H7A H 0.5453 0.7796 0.2031 0.027 Uiso 1 1 calc R . . 
H7B H 0.3912 0.6987 0.1542 0.027 Uiso 1 1 calc R . . 
H7C H 0.5332 0.5995 0.1513 0.027 Uiso 1 1 calc R . . 
C8 C 0.4944(3) 0.5742(3) 0.27442(16) 0.0159(5) Uani 1 1 d . . . 
C9 C 0.6524(2) 0.5618(3) 0.33496(16) 0.0150(5) Uani 1 1 d . . . 
H9A H 0.7041 0.6646 0.3230 0.018 Uiso 1 1 calc R . . 
H9B H 0.6522 0.5697 0.3978 0.018 Uiso 1 1 calc R . . 
C10 C 0.7398(3) 0.4005(3) 0.32635(16) 0.0155(5) Uani 1 1 d . . . 
C11 C 0.9751(3) 0.5148(4) 0.40666(18) 0.0208(6) Uani 1 1 d . . . 
C12 C 1.1038(3) 0.4806(4) 0.4855(2) 0.0314(7) Uani 1 1 d . . . 
H12A H 1.1783 0.5662 0.4869 0.047 Uiso 1 1 calc R . . 
H12B H 1.1406 0.3644 0.4805 0.047 Uiso 1 1 calc R . . 
H12C H 1.0767 0.4888 0.5406 0.047 Uiso 1 1 calc R . . 
C13 C 0.7779(3) 0.3533(3) 0.23876(16) 0.0169(5) Uani 1 1 d . . . 
H13A H 0.7333 0.4358 0.1902 0.020 Uiso 1 1 calc R . . 
H13B H 0.8829 0.3533 0.2495 0.020 Uiso 1 1 calc R . . 
C14 C 0.7144(3) 0.1672(4) 0.21527(16) 0.0166(5) Uani 1 1 d . . . 
C15 C 0.5990(3) 0.1750(3) 0.26145(15) 0.0155(5) Uani 1 1 d . . . 
H15A H 0.5653 0.0561 0.2701 0.019 Uiso 1 1 calc R . . 
C16 C 0.4760(2) 0.2822(3) 0.20120(15) 0.0156(5) Uani 1 1 d . . . 
H16A H 0.5247 0.3639 0.1704 0.019 Uiso 1 1 calc R . . 
C17 C 0.3942(3) 0.1601(3) 0.12708(17) 0.0196(6) Uani 1 1 d . . . 
H17A H 0.3568 0.0596 0.1522 0.024 Uiso 1 1 calc R . . 
H17B H 0.3129 0.2206 0.0844 0.024 Uiso 1 1 calc R . . 
C18 C 0.5029(3) 0.1027(3) 0.08145(17) 0.0205(6) Uani 1 1 d . . . 
H18A H 0.4684 0.0505 0.0242 0.025 Uiso 1 1 calc R . . 
C19 C 0.6440(3) 0.1214(3) 0.11687(16) 0.0179(5) Uani 1 1 d . . . 
C20 C 0.7472(3) 0.0846(4) 0.06467(17) 0.0225(6) Uani 1 1 d . . . 
H20A H 0.7957 0.1935 0.0574 0.027 Uiso 1 1 calc R . . 
H20B H 0.6927 0.0432 0.0044 0.027 Uiso 1 1 calc R . . 
C21 C 0.8598(3) -0.0488(4) 0.10862(18) 0.0214(6) Uani 1 1 d . . . 
C22 C 0.9349(3) -0.0025(4) 0.20543(18) 0.0209(6) Uani 1 1 d . . . 
H22A H 0.9924 0.1036 0.2078 0.025 Uiso 1 1 calc R . . 
H22B H 1.0009 -0.0971 0.2339 0.025 Uiso 1 1 calc R . . 
C23 C 0.8272(3) 0.0271(3) 0.25724(17) 0.0184(5) Uani 1 1 d . . . 
H23A H 0.8798 0.0615 0.3191 0.022 Uiso 1 1 calc R . . 
H23B H 0.7773 -0.0830 0.2601 0.022 Uiso 1 1 calc R . . 
C24 C 0.8972(3) -0.3363(4) 0.09098(18) 0.0205(6) Uani 1 1 d . . . 
H24A H 0.8509 -0.4395 0.0571 0.025 Uiso 1 1 calc R . . 
H24B H 0.9600 -0.3732 0.1502 0.025 Uiso 1 1 calc R . . 
C25 C 0.9811(3) -0.2365(4) 0.04011(17) 0.0210(5) Uani 1 1 d . . . 
H25A H 1.0835 -0.2698 0.0602 0.025 Uiso 1 1 calc R . . 
H25B H 0.9421 -0.2579 -0.0249 0.025 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 0.0267(10) 0.0157(9) 0.0149(8) 0.0012(7) 0.0097(7) 0.0025(8) 
O2 0.0286(10) 0.0136(9) 0.0206(9) -0.0018(8) 0.0111(7) 0.0007(8) 
O3 0.0178(8) 0.0126(9) 0.0149(8) 0.0012(7) 0.0054(6) -0.0012(7) 
O4 0.0160(9) 0.0190(10) 0.0209(9) -0.0001(8) 0.0026(7) -0.0008(8) 
O5 0.0221(10) 0.0221(10) 0.0361(11) 0.0019(9) 0.0110(8) -0.0032(9) 
O6 0.0204(9) 0.0145(9) 0.0269(9) -0.0015(8) 0.0106(7) 0.0005(8) 
O7 0.0369(12) 0.0170(10) 0.0439(12) -0.0035(9) 0.0301(10) 0.0002(9) 
C1 0.127(4) 0.0232(18) 0.0397(19) -0.0010(17) 0.048(2) 0.015(2) 
C2 0.091(3) 0.0217(17) 0.0352(18) -0.0069(14) 0.0366(19) -0.0011(19) 
C3 0.0230(14) 0.0124(12) 0.0182(13) 0.0014(10) 0.0091(10) 0.0014(11) 
C4 0.0163(12) 0.0225(14) 0.0232(13) -0.0035(12) 0.0058(10) 0.0019(11) 
C5 0.0176(13) 0.0186(14) 0.0247(14) -0.0015(11) 0.0061(10) -0.0003(11) 
C6 0.0159(12) 0.0132(12) 0.0176(12) -0.0011(10) 0.0054(9) -0.0007(10) 
C7 0.0201(13) 0.0157(13) 0.0188(12) -0.0002(11) 0.0079(10) 0.0008(10) 
C8 0.0180(12) 0.0140(13) 0.0160(12) -0.0003(10) 0.0058(9) 0.0006(10) 
C9 0.0140(12) 0.0131(12) 0.0171(13) -0.0015(10) 0.0036(10) -0.0003(10) 
C10 0.0138(12) 0.0146(13) 0.0176(12) 0.0009(10) 0.0041(9) -0.0024(10) 
C11 0.0176(13) 0.0189(14) 0.0265(14) -0.0067(12) 0.0073(10) -0.0001(11) 
C12 0.0231(15) 0.0351(17) 0.0313(16) -0.0065(14) 0.0010(12) -0.0045(13) 
C13 0.0173(12) 0.0166(13) 0.0184(12) 0.0005(10) 0.0079(9) 0.0014(11) 
C14 0.0174(12) 0.0159(13) 0.0168(12) 0.0006(10) 0.0057(10) 0.0023(10) 
C15 0.0187(12) 0.0132(12) 0.0148(12) -0.0003(10) 0.0052(9) 0.0006(10) 
C16 0.0143(12) 0.0129(12) 0.0196(12) -0.0008(11) 0.0050(9) -0.0002(11) 
C17 0.0211(13) 0.0144(13) 0.0203(13) -0.0034(11) 0.0016(10) 0.0003(10) 
C18 0.0292(14) 0.0151(13) 0.0151(12) -0.0026(11) 0.0036(10) 0.0015(11) 
C19 0.0253(13) 0.0136(12) 0.0166(12) 0.0006(11) 0.0088(10) 0.0042(11) 
C20 0.0296(14) 0.0216(15) 0.0212(14) 0.0018(11) 0.0148(11) 0.0068(12) 
C21 0.0256(14) 0.0177(14) 0.0255(14) -0.0026(11) 0.0146(11) -0.0016(11) 
C22 0.0162(13) 0.0188(14) 0.0291(14) -0.0015(11) 0.0087(11) -0.0004(11) 
C23 0.0195(13) 0.0163(13) 0.0188(13) 0.0015(10) 0.0050(10) 0.0015(11) 
C24 0.0201(13) 0.0172(14) 0.0237(13) -0.0007(11) 0.0059(10) 0.0027(11) 
C25 0.0217(13) 0.0191(13) 0.0241(13) -0.0024(12) 0.0097(10) 0.0035(12) 
  
_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 
O1 C1 1.414(4) . ? 
O1 C3 1.426(3) . ? 
O2 C2 1.418(4) . ? 
O2 C3 1.428(3) . ? 
O3 C10 1.413(3) . ? 
O3 C15 1.430(3) . ? 
O4 C11 1.352(3) . ? 
O4 C10 1.468(3) . ? 
O5 C11 1.208(3) . ? 
O6 C21 1.423(3) . ? 
O6 C24 1.431(3) . ? 
O7 C25 1.429(3) . ? 
O7 C21 1.440(3) . ? 
C1 C2 1.427(5) . ? 
C3 C8 1.547(3) . ? 
C3 C4 1.548(3) . ? 
C4 C5 1.550(4) . ? 
C5 C6 1.538(3) . ? 
C6 C16 1.532(3) . ? 
C6 C8 1.563(3) . ? 
C7 C8 1.547(3) . ? 
C8 C9 1.556(3) . ? 
C9 C10 1.541(3) . ? 
C10 C13 1.573(3) . ? 
C11 C12 1.501(4) . ? 
C13 C14 1.567(4) . ? 
C14 C15 1.516(3) . ? 
C14 C19 1.532(3) . ? 
C14 C23 1.546(4) . ? 
C15 C16 1.532(3) . ? 
C16 C17 1.525(3) . ? 
C17 C18 1.518(4) . ? 
C18 C19 1.332(4) . ? 
C19 C20 1.507(3) . ? 
C20 C21 1.515(4) . ? 
C21 C22 1.519(4) . ? 
C22 C23 1.531(4) . ? 
C24 C25 1.517(4) . ? 
  
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 O1 C3 106.1(2) . . ? 
C2 O2 C3 107.5(2) . . ? 
C10 O3 C15 105.74(17) . . ? 
C11 O4 C10 119.4(2) . . ? 
C21 O6 C24 106.37(19) . . ? 
C25 O7 C21 108.87(19) . . ? 
O1 C1 C2 106.9(2) . . ? 
O2 C2 C1 107.2(3) . . ? 
O1 C3 O2 106.1(2) . . ? 
O1 C3 C8 111.3(2) . . ? 
O2 C3 C8 112.9(2) . . ? 
O1 C3 C4 110.7(2) . . ? 
O2 C3 C4 111.7(2) . . ? 
C8 C3 C4 104.3(2) . . ? 
C3 C4 C5 105.9(2) . . ? 
C6 C5 C4 104.7(2) . . ? 
C16 C6 C5 118.6(2) . . ? 
C16 C6 C8 108.7(2) . . ? 
C5 C6 C8 103.7(2) . . ? 
C3 C8 C7 106.4(2) . . ? 
C3 C8 C9 113.1(2) . . ? 
C7 C8 C9 108.8(2) . . ? 
C3 C8 C6 99.0(2) . . ? 
C7 C8 C6 112.7(2) . . ? 
C9 C8 C6 116.2(2) . . ? 
C10 C9 C8 118.2(2) . . ? 
O3 C10 O4 100.75(18) . . ? 
O3 C10 C9 107.37(19) . . ? 
O4 C10 C9 107.87(19) . . ? 
O3 C10 C13 105.6(2) . . ? 
O4 C10 C13 109.59(19) . . ? 
C9 C10 C13 123.3(2) . . ? 
O5 C11 O4 123.9(2) . . ? 
O5 C11 C12 125.2(3) . . ? 
O4 C11 C12 110.8(2) . . ? 
C14 C13 C10 103.7(2) . . ? 
C15 C14 C19 108.6(2) . . ? 
C15 C14 C23 111.3(2) . . ? 
C19 C14 C23 108.3(2) . . ? 
C15 C14 C13 98.7(2) . . ? 
C19 C14 C13 118.4(2) . . ? 
C23 C14 C13 111.2(2) . . ? 
O3 C15 C14 104.60(19) . . ? 
O3 C15 C16 113.5(2) . . ? 
C14 C15 C16 106.62(19) . . ? 
C17 C16 C15 105.7(2) . . ? 
C17 C16 C6 125.5(2) . . ? 
C15 C16 C6 111.68(19) . . ? 
C18 C17 C16 105.0(2) . . ? 
C19 C18 C17 123.9(2) . . ? 
C18 C19 C20 122.2(2) . . ? 
C18 C19 C14 122.7(2) . . ? 
C20 C19 C14 114.9(2) . . ? 
C19 C20 C21 113.3(2) . . ? 
O6 C21 O7 105.9(2) . . ? 
O6 C21 C20 108.4(2) . . ? 
O7 C21 C20 109.3(2) . . ? 
O6 C21 C22 112.3(2) . . ? 
O7 C21 C22 109.5(2) . . ? 
C20 C21 C22 111.2(2) . . ? 
C21 C22 C23 111.4(2) . . ? 
C22 C23 C14 113.3(2) . . ? 
O6 C24 C25 103.3(2) . . ? 
O7 C25 C24 104.4(2) . . ? 
  
_diffrn_measured_fraction_theta_max    0.990 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.314 
_refine_diff_density_min   -0.381 
_refine_diff_density_rms    0.053