 
data_8
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C27 H38 O4' 
_chemical_formula_sum 
 'C27 H38 O4' 
_chemical_formula_weight          426.57 
  
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' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            19 
_space_group_name_H-M_alt         'P 21 21 21' 
_space_group_name_Hall            'P 2ac 2ab' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_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                    10.1782(2) 
_cell_length_b                    12.5203(3) 
_cell_length_c                    19.0389(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      2426.21(10) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     9862 
_cell_measurement_theta_min       2.7650 
_cell_measurement_theta_max       27.7830 
  
_exptl_crystal_description        blocks 
_exptl_crystal_colour             Colourless	 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.168 
_exptl_crystal_F_000              928 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.655 
_exptl_crystal_size_mid           0.488 
_exptl_crystal_size_min           0.328 
_exptl_absorpt_coefficient_mu     0.077 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.964 
_exptl_absorpt_correction_T_max   0.981 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             32494 
_diffrn_reflns_av_unetI/netI      0.0316 
_diffrn_reflns_av_R_equivalents   0.0462 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -25 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          2.579 
_diffrn_reflns_theta_max          28.326 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.931 
_diffrn_measured_fraction_theta_full  0.999 
_diffrn_reflns_Laue_measured_fraction_max    0.931 
_diffrn_reflns_Laue_measured_fraction_full   0.999 
_diffrn_reflns_point_group_measured_fraction_max   0.903 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              5467 
_reflns_number_gt                 4792 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.724 
_reflns_Friedel_fraction_max      0.866 
_reflns_Friedel_fraction_full     1.000 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0366P)²+0.3874P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)' 
_refine_ls_extinction_coef        0.0078(11) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1813 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    0.3(4) 
_chemical_absolute_configuration  syn 
_refine_ls_number_reflns          5467 
_refine_ls_number_parameters      287 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0479 
_refine_ls_R_factor_gt            0.0384 
_refine_ls_wR_factor_ref          0.0846 
_refine_ls_wR_factor_gt           0.0798 
_refine_ls_goodness_of_fit_ref    1.038 
_refine_ls_restrained_S_all       1.038 
_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_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.52521(13) 0.80814(10) 0.67831(7) 0.0320(3) Uani 1 1 d . . . . . 
C2 C 0.4157(2) 0.79153(17) 0.71809(10) 0.0316(4) Uani 1 1 d . . . . . 
O2 O 0.35039(16) 0.86434(13) 0.73992(8) 0.0449(4) Uani 1 1 d . . . . . 
C3 C 0.4005(2) 0.67261(17) 0.72815(10) 0.0320(5) Uani 1 1 d . . . . . 
C4 C 0.5179(2) 0.6424(2) 0.77650(11) 0.0431(5) Uani 1 1 d . . . . . 
H4A H 0.520313 0.688513 0.818734 0.052 Uiso 1 1 calc R U . . . 
H4B H 0.512278 0.566825 0.791452 0.052 Uiso 1 1 calc R U . . . 
C5 C 0.6398(2) 0.6613(2) 0.72991(10) 0.0377(5) Uani 1 1 d . . . . . 
H5A H 0.699214 0.715267 0.750695 0.045 Uiso 1 1 calc R U . . . 
H5B H 0.689081 0.594190 0.721952 0.045 Uiso 1 1 calc R U . . . 
C6 C 0.57689(18) 0.70195(15) 0.66211(9) 0.0262(4) Uani 1 1 d . . . . . 
C7 C 0.44907(17) 0.63470(14) 0.65479(9) 0.0243(4) Uani 1 1 d . . . . . 
C8 C 0.3619(2) 0.67319(16) 0.59500(10) 0.0311(4) Uani 1 1 d . . . . . 
H8A H 0.344139 0.749614 0.600761 0.047 Uiso 1 1 calc R U . . . 
H8B H 0.278917 0.633574 0.595616 0.047 Uiso 1 1 calc R U . . . 
H8C H 0.406669 0.661185 0.550104 0.047 Uiso 1 1 calc R U . . . 
C9 C 0.4696(2) 0.51454(15) 0.64795(11) 0.0341(5) Uani 1 1 d . . . . . 
H9A H 0.505512 0.498283 0.601396 0.051 Uiso 1 1 calc R U . . . 
H9B H 0.385366 0.477780 0.653913 0.051 Uiso 1 1 calc R U . . . 
H9C H 0.531260 0.490304 0.684151 0.051 Uiso 1 1 calc R U . . . 
C10 C 0.2666(2) 0.6373(2) 0.75292(13) 0.0465(6) Uani 1 1 d . . . . . 
H10A H 0.200657 0.656278 0.717578 0.070 Uiso 1 1 calc R U . . . 
H10B H 0.245687 0.672896 0.797368 0.070 Uiso 1 1 calc R U . . . 
H10C H 0.266616 0.559743 0.759909 0.070 Uiso 1 1 calc R U . . . 
C11 C 0.66070(18) 0.70921(15) 0.59718(10) 0.0261(4) Uani 1 1 d . . . . . 
O11 O 0.66713(14) 0.78286(11) 0.55734(8) 0.0385(4) Uani 1 1 d . . . . . 
O12 O 0.72445(12) 0.61600(10) 0.58973(6) 0.0272(3) Uani 1 1 d . . . . . 
C13 C 0.79525(18) 0.59902(15) 0.52376(9) 0.0252(4) Uani 1 1 d . . . . . 
H13A H 0.851881 0.662556 0.513929 0.030 Uiso 1 1 calc R U . . . 
C14 C 0.69859(18) 0.58701(15) 0.46684(10) 0.0280(4) Uani 1 1 d . . . . . 
C15 C 0.61775(18) 0.57691(16) 0.42233(10) 0.0279(4) Uani 1 1 d . . . . . 
C16 C 0.51492(19) 0.56214(15) 0.36846(10) 0.0284(4) Uani 1 1 d . . . . . 
C17 C 0.3937(2) 0.51376(19) 0.40425(12) 0.0408(5) Uani 1 1 d . . . . . 
H17A H 0.363651 0.561514 0.441747 0.061 Uiso 1 1 calc R U . . . 
H17B H 0.416532 0.444101 0.424300 0.061 Uiso 1 1 calc R U . . . 
H17C H 0.323380 0.504752 0.369576 0.061 Uiso 1 1 calc R U . . . 
C18 C 0.4802(2) 0.66990(18) 0.33611(13) 0.0458(6) Uani 1 1 d . . . . . 
H18A H 0.410703 0.660253 0.301055 0.069 Uiso 1 1 calc R U . . . 
H18B H 0.558195 0.700293 0.313498 0.069 Uiso 1 1 calc R U . . . 
H18C H 0.449381 0.718422 0.372990 0.069 Uiso 1 1 calc R U . . . 
C19 C 0.5667(2) 0.4877(2) 0.31098(12) 0.0462(6) Uani 1 1 d . . . . . 
H19A H 0.590701 0.418796 0.331744 0.069 Uiso 1 1 calc R U . . . 
H19B H 0.644279 0.519837 0.288967 0.069 Uiso 1 1 calc R U . . . 
H19C H 0.498375 0.476873 0.275436 0.069 Uiso 1 1 calc R U . . . 
C20 C 0.88262(17) 0.50090(14) 0.53464(9) 0.0230(4) Uani 1 1 d . . . . . 
C21 C 0.96308(19) 0.48115(16) 0.46726(10) 0.0292(4) Uani 1 1 d . . . . . 
H21A H 0.902887 0.467821 0.427364 0.035 Uiso 1 1 calc R U . . . 
H21B H 1.016227 0.545210 0.456229 0.035 Uiso 1 1 calc R U . . . 
C22 C 0.97891(19) 0.52190(15) 0.59537(10) 0.0280(4) Uani 1 1 d . . . . . 
H22A H 1.032367 0.585987 0.584830 0.034 Uiso 1 1 calc R U . . . 
H22B H 0.929158 0.535565 0.639140 0.034 Uiso 1 1 calc R U . . . 
C23 C 0.80142(18) 0.40077(15) 0.55109(10) 0.0278(4) Uani 1 1 d . . . . . 
H23A H 0.749643 0.412427 0.594439 0.033 Uiso 1 1 calc R U . . . 
H23B H 0.739418 0.386638 0.512121 0.033 Uiso 1 1 calc R U . . . 
C24 C 1.05381(19) 0.38454(17) 0.47746(11) 0.0336(5) Uani 1 1 d . . . . . 
H24A H 1.105401 0.372212 0.433501 0.040 Uiso 1 1 calc R U . . . 
C25 C 1.1480(2) 0.40605(19) 0.53824(12) 0.0381(5) Uani 1 1 d . . . . . 
H25A H 1.202449 0.469541 0.527613 0.046 Uiso 1 1 calc R U . . . 
H25B H 1.207258 0.344127 0.544680 0.046 Uiso 1 1 calc R U . . . 
C26 C 1.0692(2) 0.42525(17) 0.60558(11) 0.0348(5) Uani 1 1 d . . . . . 
H26A H 1.130827 0.439284 0.645422 0.042 Uiso 1 1 calc R U . . . 
C27 C 0.9860(2) 0.32647(17) 0.62203(12) 0.0404(5) Uani 1 1 d . . . . . 
H27A H 1.043973 0.263999 0.629507 0.049 Uiso 1 1 calc R U . . . 
H27B H 0.934958 0.338532 0.665571 0.049 Uiso 1 1 calc R U . . . 
C28 C 0.8925(2) 0.30448(16) 0.56090(12) 0.0349(5) Uani 1 1 d . . . . . 
H28A H 0.838701 0.239678 0.571623 0.042 Uiso 1 1 calc R U . . . 
C29 C 0.9713(2) 0.28548(17) 0.49364(12) 0.0396(5) Uani 1 1 d . . . . . 
H29A H 1.029397 0.222739 0.499694 0.048 Uiso 1 1 calc R U . . . 
H29B H 0.910749 0.270828 0.454102 0.048 Uiso 1 1 calc R U . . . 
  
  
_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 C2 1.364(2) . ? 
O1 C6 1.463(2) . ? 
C2 O2 1.202(2) . ? 
C2 C3 1.509(3) . ? 
C3 C10 1.508(3) . ? 
C3 C4 1.555(3) . ? 
C3 C7 1.556(3) . ? 
C4 C5 1.543(3) . ? 
C5 C6 1.528(3) . ? 
C6 C11 1.505(3) . ? 
C6 C7 1.556(3) . ? 
C7 C8 1.521(3) . ? 
C7 C9 1.525(3) . ? 
C11 O11 1.196(2) . ? 
C11 O12 1.343(2) . ? 
O12 C13 1.464(2) . ? 
C13 C14 1.471(3) . ? 
C13 C20 1.531(2) . ? 
C14 C15 1.188(3) . ? 
C15 C16 1.477(3) . ? 
C16 C18 1.525(3) . ? 
C16 C19 1.531(3) . ? 
C16 C17 1.534(3) . ? 
C20 C23 1.534(2) . ? 
C20 C22 1.538(2) . ? 
C20 C21 1.542(3) . ? 
C21 C24 1.534(3) . ? 
C22 C26 1.532(3) . ? 
C23 C28 1.532(3) . ? 
C24 C25 1.527(3) . ? 
C24 C29 1.529(3) . ? 
C25 C26 1.531(3) . ? 
C26 C27 1.531(3) . ? 
C27 C28 1.528(3) . ? 
C28 C29 1.530(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 
C2 O1 C6 105.80(14) . . ? 
O2 C2 O1 121.9(2) . . ? 
O2 C2 C3 130.3(2) . . ? 
O1 C2 C3 107.75(16) . . ? 
C10 C3 C2 114.95(18) . . ? 
C10 C3 C4 115.97(18) . . ? 
C2 C3 C4 103.65(18) . . ? 
C10 C3 C7 118.58(19) . . ? 
C2 C3 C7 98.89(15) . . ? 
C4 C3 C7 102.30(15) . . ? 
C5 C4 C3 103.90(15) . . ? 
C6 C5 C4 101.54(16) . . ? 
O1 C6 C11 108.79(15) . . ? 
O1 C6 C5 106.00(15) . . ? 
C11 C6 C5 118.47(16) . . ? 
O1 C6 C7 102.13(14) . . ? 
C11 C6 C7 115.67(15) . . ? 
C5 C6 C7 104.20(16) . . ? 
C8 C7 C9 109.19(16) . . ? 
C8 C7 C3 112.95(15) . . ? 
C9 C7 C3 114.92(16) . . ? 
C8 C7 C6 112.52(15) . . ? 
C9 C7 C6 115.27(15) . . ? 
C3 C7 C6 91.16(14) . . ? 
O11 C11 O12 125.21(18) . . ? 
O11 C11 C6 126.78(17) . . ? 
O12 C11 C6 107.96(15) . . ? 
C11 O12 C13 117.06(14) . . ? 
O12 C13 C14 108.52(14) . . ? 
O12 C13 C20 106.64(14) . . ? 
C14 C13 C20 113.96(15) . . ? 
C15 C14 C13 178.1(2) . . ? 
C14 C15 C16 178.2(2) . . ? 
C15 C16 C18 109.51(16) . . ? 
C15 C16 C19 109.17(17) . . ? 
C18 C16 C19 109.25(18) . . ? 
C15 C16 C17 108.12(16) . . ? 
C18 C16 C17 110.02(18) . . ? 
C19 C16 C17 110.74(17) . . ? 
C13 C20 C23 111.75(14) . . ? 
C13 C20 C22 109.55(15) . . ? 
C23 C20 C22 109.24(15) . . ? 
C13 C20 C21 108.94(15) . . ? 
C23 C20 C21 108.96(15) . . ? 
C22 C20 C21 108.33(14) . . ? 
C24 C21 C20 109.93(16) . . ? 
C26 C22 C20 110.03(15) . . ? 
C28 C23 C20 109.99(14) . . ? 
C25 C24 C29 109.59(18) . . ? 
C25 C24 C21 109.56(16) . . ? 
C29 C24 C21 109.54(16) . . ? 
C24 C25 C26 109.48(16) . . ? 
C27 C26 C25 109.51(18) . . ? 
C27 C26 C22 109.43(16) . . ? 
C25 C26 C22 109.38(17) . . ? 
C28 C27 C26 109.52(17) . . ? 
C27 C28 C29 109.82(17) . . ? 
C27 C28 C23 109.14(17) . . ? 
C29 C28 C23 109.73(17) . . ? 
C24 C29 C28 109.30(16) . . ? 
  
_refine_diff_density_max    0.215 
_refine_diff_density_min   -0.186 
_refine_diff_density_rms    0.035 
  
  
  
#===END

