 
data_racem 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C25 H26 O3' 
_chemical_formula_weight          374.46 
 
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            ? 
_symmetry_space_group_name_H-M    ? 
 
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' 
 
_cell_length_a                    8.6709(9) 
_cell_length_b                    12.9435(16) 
_cell_length_c                    17.587(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1973.8(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.80 
_exptl_crystal_size_mid           0.40 
_exptl_crystal_size_min           0.40 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.260 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              800 
_exptl_absorpt_coefficient_mu     0.081 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   0.9378 
_exptl_absorpt_correction_T_max   0.9682 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             23717 
_diffrn_reflns_av_R_equivalents   0.0416 
_diffrn_reflns_av_sigmaI/netI     0.0204 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          3.06 
_diffrn_reflns_theta_max          25.04 
_reflns_number_total              3268 
_reflns_number_gt                 2918 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_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)+(0.0592P)²+1.0291P] 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_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.5(19) 
_refine_ls_number_reflns          3268 
_refine_ls_number_parameters      286 
_refine_ls_number_restraints      36 
_refine_ls_R_factor_all           0.0537 
_refine_ls_R_factor_gt            0.0470 
_refine_ls_wR_factor_ref          0.1243 
_refine_ls_wR_factor_gt           0.1190 
_refine_ls_goodness_of_fit_ref    1.048 
_refine_ls_restrained_S_all       1.043 
_refine_ls_shift/su_max           0.201 
_refine_ls_shift/su_mean          0.006 
 
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 0.60530(15) 0.24432(13) 0.08720(7) 0.0214(3) Uani 1 1 d . . . 
C2 C 0.6901(3) 0.14903(18) 0.08399(15) 0.0267(6) Uani 1 1 d . . . 
C3 C 0.8120(3) 0.14504(18) 0.14821(14) 0.0237(6) Uani 1 1 d . . . 
H3 H 0.7544 0.1461 0.1975 0.028 Uiso 1 1 calc R . . 
C4 C 0.9172(2) 0.2426(2) 0.14723(10) 0.0255(5) Uani 1 1 d . . . 
C5 C 0.8172(3) 0.34048(18) 0.14552(14) 0.0232(6) Uani 1 1 d . . . 
H5 H 0.7588 0.3423 0.1945 0.028 Uiso 1 1 calc R . . 
C6 C 0.6964(3) 0.33610(18) 0.08121(14) 0.0244(5) Uani 1 1 d . . . 
O12 O 0.7711(6) 0.1612(4) 0.0119(3) 0.0382(16) Uani 0.440(7) 1 d P . . 
H12 H 0.7069 0.1624 -0.0239 0.057 Uiso 0.440(7) 1 calc PR . . 
C13 C 0.9045(4) 0.0445(2) 0.14653(18) 0.0366(7) Uani 1 1 d . . . 
H13A H 0.9599 0.0393 0.0981 0.055 Uiso 1 1 calc R . . 
H13B H 0.8343 -0.0143 0.1519 0.055 Uiso 1 1 calc R . . 
H13C H 0.9787 0.0443 0.1886 0.055 Uiso 1 1 calc R . . 
O14 O 1.01867(17) 0.23938(19) 0.08231(7) 0.0368(4) Uani 1 1 d . . . 
H14 H 0.9746 0.2664 0.0447 0.055 Uiso 1 1 calc R . . 
C15 C 0.9138(4) 0.4400(2) 0.14219(17) 0.0352(7) Uani 1 1 d . . . 
H15A H 0.9891 0.4398 0.1837 0.053 Uiso 1 1 calc R . . 
H15B H 0.8458 0.5000 0.1474 0.053 Uiso 1 1 calc R . . 
H15C H 0.9680 0.4434 0.0934 0.053 Uiso 1 1 calc R . . 
O16 O 0.7777(3) 0.3285(2) 0.00937(14) 0.0131(9) Uani 0.560(7) 1 d P . . 
H16 H 0.7148 0.3141 -0.0254 0.020 Uiso 0.560(7) 1 calc PR . . 
C101 C 0.5822(3) 0.42499(19) 0.08723(15) 0.0266(6) Uani 1 1 d U . . 
C102 C 0.4706(4) 0.4255(2) 0.14382(17) 0.0322(6) Uani 1 1 d U . . 
H102 H 0.4636 0.3688 0.1779 0.039 Uiso 1 1 calc R . . 
C103 C 0.3693(4) 0.5075(2) 0.1512(2) 0.0415(8) Uani 1 1 d U . . 
H103 H 0.2924 0.5069 0.1897 0.050 Uiso 1 1 calc R . . 
C104 C 0.3816(4) 0.5915(2) 0.1012(2) 0.0479(9) Uani 1 1 d U . . 
H104 H 0.3128 0.6484 0.1055 0.057 Uiso 1 1 calc R . . 
C105 C 0.4937(5) 0.5911(2) 0.0460(2) 0.0488(9) Uani 1 1 d U . . 
H105 H 0.5025 0.6483 0.0123 0.059 Uiso 1 1 calc R . . 
C106 C 0.5936(4) 0.50883(18) 0.03882(18) 0.0367(7) Uani 1 1 d U . . 
H106 H 0.6707 0.5097 0.0004 0.044 Uiso 1 1 calc R . . 
C201 C 1.0180(2) 0.2424(2) 0.21891(10) 0.0235(4) Uani 1 1 d U . . 
C202 C 0.9468(3) 0.2377(3) 0.28973(12) 0.0445(7) Uani 1 1 d U . . 
H202 H 0.8375 0.2343 0.2927 0.053 Uiso 1 1 calc R . . 
C203 C 1.0338(3) 0.2380(3) 0.35626(12) 0.0464(7) Uani 1 1 d U . . 
H203 H 0.9834 0.2335 0.4041 0.056 Uiso 1 1 calc R . . 
C204 C 1.1912(3) 0.2445(2) 0.35345(11) 0.0314(5) Uani 1 1 d U . . 
H204 H 1.2503 0.2454 0.3989 0.038 Uiso 1 1 calc R . . 
C205 C 1.2624(2) 0.2499(2) 0.28358(11) 0.0305(5) Uani 1 1 d U . . 
H205 H 1.3717 0.2542 0.2810 0.037 Uiso 1 1 calc R . . 
C206 C 1.1764(2) 0.2491(2) 0.21667(10) 0.0254(4) Uani 1 1 d U . . 
H206 H 1.2276 0.2533 0.1690 0.030 Uiso 1 1 calc R . . 
C301 C 0.5747(3) 0.06355(18) 0.09317(15) 0.0264(6) Uani 1 1 d U . . 
C302 C 0.4649(4) 0.0692(2) 0.15054(17) 0.0301(6) Uani 1 1 d U . . 
H302 H 0.4624 0.1282 0.1827 0.036 Uiso 1 1 calc R . . 
C303 C 0.3586(4) -0.0098(2) 0.1618(2) 0.0397(7) Uani 1 1 d U . . 
H303 H 0.2843 -0.0045 0.2013 0.048 Uiso 1 1 calc R . . 
C304 C 0.3613(4) -0.0955(2) 0.1156(2) 0.0479(9) Uani 1 1 d U . . 
H304 H 0.2889 -0.1497 0.1227 0.057 Uiso 1 1 calc R . . 
C305 C 0.4701(5) -0.1017(2) 0.0591(2) 0.0528(10) Uani 1 1 d U . . 
H305 H 0.4725 -0.1612 0.0276 0.063 Uiso 1 1 calc R . . 
C306 C 0.5766(4) -0.0237(2) 0.04672(17) 0.0386(8) Uani 1 1 d U . . 
H306 H 0.6502 -0.0296 0.0069 0.046 Uiso 1 1 calc R . . 
 
 
_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 C6 1.430(3) . y 
O1 C2 1.437(3) . y 
C2 O12 1.458(6) . y 
C2 C301 1.500(4) . y 
C2 C3 1.548(4) . y 
C3 C13 1.529(4) . y 
C3 C4 1.558(4) . y 
C3 H3 1.0000 . ? 
C4 O14 1.442(2) . y 
C4 C5 1.536(4) . y 
C4 C201 1.534(2) . y 
C5 C15 1.537(4) . y 
C5 C6 1.543(4) . y 
C5 H5 1.0000 . ? 
C6 O16 1.450(4) . y 
C6 C101 1.521(4) . y 
O12 H12 0.8400 . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
O14 H14 0.8400 . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 0.9800 . ? 
O16 H16 0.8400 . ? 
C101 C106 1.383(3) . y 
C101 C102 1.388(4) . y 
C102 C103 1.383(4) . y 
C102 H102 0.9500 . ? 
C103 C104 1.403(5) . y 
C103 H103 0.9500 . ? 
C104 C105 1.375(5) . y 
C104 H104 0.9500 . ? 
C105 C106 1.379(5) . y 
C105 H105 0.9500 . ? 
C106 H106 0.9500 . ? 
C201 C206 1.377(3) . y 
C201 C202 1.392(3) . y 
C202 C203 1.392(3) . y 
C202 H202 0.9500 . ? 
C203 C204 1.368(4) . y 
C203 H203 0.9500 . y 
C204 C205 1.377(3) . y 
C204 H204 0.9500 . ? 
C205 C206 1.393(3) . y 
C205 H205 0.9500 . ? 
C206 H206 0.9500 . ? 
C301 C302 1.389(4) . y 
C301 C306 1.394(3) . y 
C302 C303 1.391(4) . y 
C302 H302 0.9500 . ? 
C303 C304 1.376(5) . y 
C303 H303 0.9500 . ? 
C304 C305 1.373(5) . y 
C304 H304 0.9500 . ? 
C305 C306 1.385(5) . y 
C305 H305 0.9500 . ? 
C306 H306 0.9500 . ? 
 
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 
C6 O1 C2 115.31(16) . . y
O1 C2 O12 100.8(2) . . y 
O1 C2 C301 106.7(2) . . y 
O12 C2 C301 119.7(3) . . y 
O1 C2 C3 110.44(18) . . y 
O12 C2 C3 108.0(3) . . y 
C301 C2 C3 110.6(2) . . y 
C13 C3 C2 111.9(2) . . y 
C13 C3 C4 112.5(2) . . y 
C2 C3 C4 111.4(2) . . y 
C13 C3 H3 106.9 . . ? 
C2 C3 H3 106.9 . . ? 
C4 C3 H3 106.9 . . ? 
O14 C4 C5 110.7(2) . . y 
O14 C4 C201 107.60(16) . . y 
C5 C4 C201 109.82(19) . . y 
O14 C4 C3 110.06(19) . . y 
C5 C4 C3 109.78(16) . . y 
C201 C4 C3 108.9(2) . . y 
C15 C5 C4 112.6(2) . . y 
C15 C5 C6 111.9(2) . . y 
C4 C5 C6 111.56(19) . . y 
C15 C5 H5 106.8 . . ? 
C4 C5 H5 106.8 . . ? 
C6 C5 H5 106.8 . . ? 
O1 C6 O16 106.02(19) . . y 
O1 C6 C101 105.3(2) . . y 
O16 C6 C101 115.4(2) . . y 
O1 C6 C5 110.57(18) . . y
O16 C6 C5 108.1(2) . . y 
C101 C6 C5 111.3(2) . . y 
C2 O12 H12 109.5 . . ? 
C3 C13 H13A 109.5 . . ? 
C3 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C3 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C4 O14 H14 109.5 . . ? 
C5 C15 H15A 109.5 . . ? 
C5 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C5 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C6 O16 H16 109.5 . . ? 
C106 C101 C102 119.2(3) . . y 
C106 C101 C6 120.3(3) . . y 
C102 C101 C6 120.5(2) . . y 
C101 C102 C103 120.9(3) . . y 
C101 C102 H102 119.5 . . ? 
C103 C102 H102 119.5 . . ? 
C102 C103 C104 119.2(3) . . y 
C102 C103 H103 120.4 . . ? 
C104 C103 H103 120.4 . . ? 
C105 C104 C103 119.6(3) . . y 
C105 C104 H104 120.2 . . ? 
C103 C104 H104 120.2 . . ? 
C106 C105 C104 120.8(3) . . y 
C106 C105 H105 119.6 . . ? 
C104 C105 H105 119.6 . . ? 
C105 C106 C101 120.3(3) . . y 
C105 C106 H106 119.8 . . ? 
C101 C106 H106 119.8 . . ? 
C206 C201 C202 118.12(18) . . y 
C206 C201 C4 123.03(17) . . y 
C202 C201 C4 118.83(19) . . y 
C201 C202 C203 120.7(2) . . y 
C201 C202 H202 119.6 . . ? 
C203 C202 H202 119.6 . . ? 
C204 C203 C202 120.7(2) . . y 
C204 C203 H203 119.7 . . ? 
C202 C203 H203 119.7 . . ? 
C203 C204 C205 118.87(18) . . y 
C203 C204 H204 120.6 . . ? 
C205 C204 H204 120.6 . . ? 
C204 C205 C206 120.9(2) . . y 
C204 C205 H205 119.6 . . ? 
C206 C205 H205 119.6 . . ? 
C201 C206 C205 120.67(18) . . y 
C201 C206 H206 119.7 . . ? 
C205 C206 H206 119.7 . . ? 
C302 C301 C306 118.5(3) . . y 
C302 C301 C2 119.7(2) . . y 
C306 C301 C2 121.8(3) . . y 
C303 C302 C301 121.3(3) . . y 
C303 C302 H302 119.4 . . ? 
C301 C302 H302 119.4 . . ? 
C304 C303 C302 119.9(3) . . y 
C304 C303 H303 120.1 . . ? 
C302 C303 H303 120.1 . . ? 
C305 C304 C303 119.1(3) . . y 
C305 C304 H304 120.5 . . ? 
C303 C304 H304 120.5 . . ? 
C304 C305 C306 122.0(3) . . y 
C304 C305 H305 119.0 . . ? 
C306 C305 H305 119.0 . . ? 
C305 C306 C301 119.4(3) . . y 
C305 C306 H306 120.3 . . ? 
C301 C306 H306 120.3 . . ? 
 
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 
O12 H12 O14  0.84 2.31 3.032(5) 144.2 4_455 
O16 H16 O14  0.84 2.09 2.901(3) 161.7 4_455 
O14 H14 O16  0.84 1.99 2.710(3) 143.7 . 
O14 H14 O12  0.84 2.30 2.676(5) 107.4 . 
O14 H14 O1  0.84 2.59 3.0815(18) 119.0 4 
 
_diffrn_measured_fraction_theta_max    0.925 
_diffrn_reflns_theta_full              25.04 
_diffrn_measured_fraction_theta_full   0.925 
_refine_diff_density_max    0.197 
_refine_diff_density_min   -0.203 
_refine_diff_density_rms    0.040 
