 
data_dd27esa 
 
_audit_creation_method            'SHELXL-2014/7' 
_audit_update_record 
; 
? 
; 
 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic 
; 
? 
; 
 
_chemical_name_common            ? 
_chemical_melting_point          ? 
_chemical_formula_moiety         'C36 H42 O7' 
_chemical_formula_sum 
 'C36 H42 O7' 
_chemical_formula_structural     ? 
_chemical_formula_weight          586.69 
 
_chemical_formula_iupac          ? 
_chemical_formula_analytical     ? 
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' 
 
_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                    12.9410(3) 
_cell_length_b                    13.1806(3) 
_cell_length_c                    18.8817(4) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      3220.65(12) 
_cell_formula_units_Z             4 
_cell_measurement_temperature    100(2) 
_cell_measurement_reflns_used      9926 
_cell_measurement_theta_min        3.42 
_cell_measurement_theta_max       68.24 
_exptl_crystal_description       'column' 
_exptl_crystal_colour            'colourless' 
_exptl_crystal_density_meas      ? 
_exptl_crystal_density_method    'not measured' 
_exptl_crystal_density_diffrn     1.210 
_exptl_crystal_F_000              1256 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max          0.354 
_exptl_crystal_size_mid          0.163 
_exptl_crystal_size_min          0.116 
_exptl_crystal_id                dd27esa 
 
_exptl_crystal_preparation 
; 
The data crystal was mounted using oil (Paratone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (3 -2 3) scattering 
planes roughly normal to the spindle axis. 
; 
_exptl_absorpt_coefficient_mu     0.670 
_shelx_estimated_absorpt_T_min    0.797 
_shelx_estimated_absorpt_T_max    0.926 
_exptl_absorpt_correction_type   'integration' 
_exptl_absorpt_correction_T_min  0.8218 
_exptl_absorpt_correction_T_max  0.9388 
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker, 2014)' 
 
_exptl_absorpt_special_details    ? 
_exptl_special_details 
; 
One distinct cell was identified using APEX2 (Bruker, 2014). 
10 frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2014) then corrected for absorption by 
integration using SADABS v2014/5 (Bruker, 2014). 
No decay correction was applied. 
; 
 
_diffrn_ambient_temperature      100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_wavelength_id  dd27esa 
_diffrn_radiation_type           'CuK\a' 
_diffrn_radiation_source         'microfocus sealed tube' 
_diffrn_radiation_monochromator  'multilayer mirrors' 
_diffrn_source                    ? 
_diffrn_standards_number         ? 
_diffrn_standards_decay_%        ? 
_diffrn_standards_interval_time  ? 
 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100' 
_diffrn_measurement_method       'profile data from φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number            26546 
 
_diffrn_reflns_av_unetI/netI      0.0272 
_diffrn_reflns_av_R_equivalents   0.0365 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          4.090 
_diffrn_reflns_theta_max          68.447 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.998 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    0.998 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   0.996 
_diffrn_reflns_point_group_measured_fraction_full  0.999 
_reflns_number_total              5895 
_reflns_number_gt                 5567 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.777 
_reflns_Friedel_fraction_max      0.994 
_reflns_Friedel_fraction_full     0.998 
 
_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       'APEX2 V2014.9-0 (Bruker, 2014)' 
 
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)' 
_computing_data_reduction 
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/5, (Bruker, 2012 & 2014) 
; 
_computing_structure_solution    'SHELX-2014-7 (Sheldrick, 2015)' 
_computing_structure_refinement  'SHELX-2014-7 (Sheldrick, 2015)' 
_computing_molecular_graphics 
; 
SHELXTL v2014-7 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
; 
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)' 
 
_refine_special_details 
; 
Structure was phased by direct methods (Sheldrick, 2015). 
Systematic conditions suggested the unambiguous space group. 
The space group choice was confirmed by successful convergence of the 
full-matrix least-squares refinement on F². The final difference Fourier 
map had no significant features.  A final analysis of variance between 
observed and calculated structure factors showed little dependence on 
amplitude or resolution. 
; 
 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0417P)²+1.0499P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 'Flack (1983),  2578 Friedels' 
_refine_ls_abs_structure_Flack    0.08(8) 
_chemical_absolute_configuration ad 
_chemical_compound_source        ? 
 
_refine_ls_number_reflns          5895 
_refine_ls_number_parameters      397 
_refine_ls_number_restraints      31 
_refine_ls_R_factor_all           0.0427 
_refine_ls_R_factor_gt            0.0391 
_refine_ls_wR_factor_ref          0.0971 
_refine_ls_wR_factor_gt           0.0943 
_refine_ls_goodness_of_fit_ref    1.165 
_refine_ls_restrained_S_all       1.192 
_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 0.54395(14) 0.29022(13) 0.77177(10) 0.0224(4) Uani 1 1 d . . . . . 
O2 O 0.81173(15) 0.29584(15) 0.73156(11) 0.0283(4) Uani 1 1 d . . . . . 
O3 O 0.64299(16) 0.44078(14) 0.83963(11) 0.0275(4) Uani 1 1 d . . . . . 
O4 O 0.7008(2) 0.32055(16) 0.91444(12) 0.0504(7) Uani 1 1 d . . . . . 
O5 O 0.83378(14) 0.06241(13) 0.59490(10) 0.0211(4) Uani 1 1 d . . . . . 
O6 O 0.99028(15) 0.13352(14) 0.60968(11) 0.0263(4) Uani 1 1 d . . . . . 
O7 O 1.13496(16) -0.71599(14) 0.58066(12) 0.0281(5) Uani 1 1 d D . . . . 
H7 H 1.094(2) -0.757(2) 0.5951(19) 0.042 Uiso 1 1 d D U . . . 
C1 C 0.76160(19) -0.04297(18) 0.68832(14) 0.0190(5) Uani 1 1 d . . . . . 
H1A H 0.6994 -0.0379 0.6571 0.023 Uiso 1 1 calc R U . . . 
C2 C 0.8587(2) -0.01851(18) 0.64446(13) 0.0180(5) Uani 1 1 d . . . . . 
H2A H 0.9151 0.0046 0.6768 0.022 Uiso 1 1 calc R U . . . 
C3 C 0.8901(2) -0.11926(18) 0.60980(14) 0.0176(5) Uani 1 1 d . . . . . 
C4 C 1.0004(2) -0.12575(18) 0.58209(14) 0.0216(5) Uani 1 1 d . . . . . 
H4A H 1.0483 -0.0970 0.6177 0.026 Uiso 1 1 calc R U . . . 
H4B H 1.0066 -0.0849 0.5383 0.026 Uiso 1 1 calc R U . . . 
C5 C 1.0312(2) -0.23648(19) 0.56629(14) 0.0227(6) Uani 1 1 d . . . . . 
H5A H 0.9896 -0.2621 0.5261 0.027 Uiso 1 1 calc R U . . . 
H5B H 1.1049 -0.2388 0.5523 0.027 Uiso 1 1 calc R U . . . 
C6 C 1.01436(19) -0.30558(18) 0.63102(13) 0.0168(5) Uani 1 1 d . . . . . 
H6A H 1.0619 -0.2804 0.6689 0.020 Uiso 1 1 calc R U . . . 
C7 C 1.04325(19) -0.41606(18) 0.61773(13) 0.0165(5) Uani 1 1 d . . . . . 
C8 C 1.1228(2) -0.4413(2) 0.57114(14) 0.0197(5) Uani 1 1 d . . . . . 
H8A H 1.1577 -0.3883 0.5468 0.024 Uiso 1 1 calc R U . . . 
C9 C 1.1530(2) -0.5406(2) 0.55893(14) 0.0212(5) Uani 1 1 d . . . . . 
H9A H 1.2075 -0.5551 0.5268 0.025 Uiso 1 1 calc R U . . . 
C10 C 1.1025(2) -0.61901(19) 0.59430(15) 0.0211(6) Uani 1 1 d . . . . . 
C11 C 1.0233(2) -0.59623(19) 0.64084(14) 0.0188(5) Uani 1 1 d . . . . . 
H11A H 0.9886 -0.6498 0.6646 0.023 Uiso 1 1 calc R U . . . 
C12 C 0.99328(19) -0.49574(19) 0.65372(13) 0.0172(5) Uani 1 1 d . . . . . 
C13 C 0.9067(2) -0.47568(19) 0.70589(14) 0.0203(5) Uani 1 1 d . . . . . 
H13A H 0.9189 -0.5164 0.7491 0.024 Uiso 1 1 calc R U . . . 
H13B H 0.8407 -0.4986 0.6848 0.024 Uiso 1 1 calc R U . . . 
C14 C 0.8965(2) -0.36450(19) 0.72665(14) 0.0204(5) Uani 1 1 d . . . . . 
H14A H 0.9520 -0.3463 0.7605 0.025 Uiso 1 1 calc R U . . . 
H14B H 0.8292 -0.3532 0.7503 0.025 Uiso 1 1 calc R U . . . 
C15 C 0.90422(19) -0.29736(18) 0.66097(13) 0.0157(5) Uani 1 1 d . . . . . 
H15A H 0.8542 -0.3224 0.6246 0.019 Uiso 1 1 calc R U . . . 
C16 C 0.88147(19) -0.18638(18) 0.67636(13) 0.0158(5) Uani 1 1 d . . . . . 
H16A H 0.9365 -0.1627 0.7097 0.019 Uiso 1 1 calc R U . . . 
C17 C 0.7776(2) -0.15651(18) 0.71014(15) 0.0203(5) Uani 1 1 d . . . . . 
H17A H 0.7805 -0.1635 0.7623 0.024 Uiso 1 1 calc R U . . . 
H17B H 0.7209 -0.1994 0.6917 0.024 Uiso 1 1 calc R U . . . 
C18 C 0.7493(2) 0.02891(19) 0.74916(14) 0.0209(5) Uani 1 1 d . . . . . 
H18A H 0.8023 0.0294 0.7840 0.025 Uiso 1 1 calc R U . . . 
C19 C 0.6709(2) 0.09171(19) 0.75835(15) 0.0229(6) Uani 1 1 d . . . . . 
H19A H 0.6160 0.0906 0.7249 0.027 Uiso 1 1 calc R U . . . 
C20 C 0.6646(2) 0.16446(19) 0.81911(15) 0.0237(6) Uani 1 1 d . . . . . 
H20A H 0.7291 0.1598 0.8471 0.028 Uiso 1 1 calc R U . . . 
H20B H 0.6067 0.1441 0.8503 0.028 Uiso 1 1 calc R U . . . 
C21 C 0.6488(2) 0.27453(19) 0.79629(14) 0.0202(5) Uani 1 1 d . . . . . 
C22 C 0.5480(2) 0.33903(19) 0.70771(14) 0.0210(5) Uani 1 1 d . . . . . 
C23 C 0.4626(2) 0.3756(2) 0.67210(16) 0.0265(6) Uani 1 1 d . . . . . 
H23A H 0.3949 0.3686 0.6909 0.032 Uiso 1 1 calc R U . . . 
C24 C 0.4802(2) 0.4229(2) 0.60798(17) 0.0339(7) Uani 1 1 d . . . . . 
H24A H 0.4232 0.4500 0.5825 0.041 Uiso 1 1 calc R U . . . 
C25 C 0.5795(3) 0.4322(3) 0.57937(17) 0.0361(7) Uani 1 1 d . . . . . 
H25A H 0.5887 0.4638 0.5346 0.043 Uiso 1 1 calc R U . . . 
C26 C 0.6643(2) 0.3957(2) 0.61580(15) 0.0279(6) Uani 1 1 d . . . . . 
H26A H 0.7320 0.4021 0.5969 0.033 Uiso 1 1 calc R U . . . 
C27 C 0.6477(2) 0.34918(19) 0.68101(14) 0.0206(5) Uani 1 1 d . . . . . 
C28 C 0.7184(2) 0.30618(18) 0.73326(14) 0.0194(5) Uani 1 1 d . . . . . 
C29 C 0.6676(2) 0.3477(2) 0.85820(14) 0.0227(6) Uani 1 1 d . . . . . 
C30 C 0.6468(2) 0.5261(2) 0.89164(16) 0.0283(6) Uani 1 1 d D . . . . 
C31 C 0.5601(5) 0.5115(4) 0.9415(3) 0.0327(7) Uani 0.609(8) 1 d D . P A 1 
H31A H 0.4964 0.4989 0.9149 0.049 Uiso 0.609(8) 1 calc R U P A 1 
H31B H 0.5518 0.5727 0.9705 0.049 Uiso 0.609(8) 1 calc R U P A 1 
H31C H 0.5747 0.4534 0.9723 0.049 Uiso 0.609(8) 1 calc R U P A 1 
C32 C 0.6245(5) 0.6177(5) 0.8401(4) 0.0327(7) Uani 0.609(8) 1 d D . P A 1 
H32A H 0.6787 0.6210 0.8039 0.049 Uiso 0.609(8) 1 calc R U P A 1 
H32B H 0.6238 0.6812 0.8672 0.049 Uiso 0.609(8) 1 calc R U P A 1 
H32C H 0.5573 0.6080 0.8173 0.049 Uiso 0.609(8) 1 calc R U P A 1 
C33 C 0.7503(6) 0.5423(7) 0.9215(4) 0.0327(7) Uani 0.609(8) 1 d D . P A 1 
H33A H 0.8016 0.5415 0.8834 0.049 Uiso 0.609(8) 1 calc R U P A 1 
H33B H 0.7659 0.4883 0.9555 0.049 Uiso 0.609(8) 1 calc R U P A 1 
H33C H 0.7524 0.6081 0.9457 0.049 Uiso 0.609(8) 1 calc R U P A 1 
C31A C 0.5956(8) 0.4929(7) 0.9645(5) 0.0327(7) Uani 0.391(8) 1 d D . P A 2 
H31D H 0.5274 0.4635 0.9554 0.049 Uiso 0.391(8) 1 calc R U P A 2 
H31E H 0.5884 0.5523 0.9953 0.049 Uiso 0.391(8) 1 calc R U P A 2 
H31F H 0.6396 0.4423 0.9878 0.049 Uiso 0.391(8) 1 calc R U P A 2 
C32A C 0.5985(8) 0.6126(7) 0.8579(6) 0.0327(7) Uani 0.391(8) 1 d D . P A 2 
H32D H 0.6242 0.6190 0.8093 0.039 Uiso 0.391(8) 1 calc R U P A 2 
H32E H 0.6152 0.6743 0.8845 0.039 Uiso 0.391(8) 1 calc R U P A 2 
H32F H 0.5234 0.6030 0.8571 0.039 Uiso 0.391(8) 1 calc R U P A 2 
C33A C 0.7637(8) 0.5402(12) 0.9085(7) 0.0327(7) Uani 0.391(8) 1 d D . P A 2 
H33D H 0.8021 0.5497 0.8643 0.049 Uiso 0.391(8) 1 calc R U P A 2 
H33E H 0.7897 0.4798 0.9331 0.049 Uiso 0.391(8) 1 calc R U P A 2 
H33F H 0.7729 0.5998 0.9388 0.049 Uiso 0.391(8) 1 calc R U P A 2 
C34 C 0.9041(2) 0.13536(19) 0.58451(14) 0.0203(5) Uani 1 1 d . . . . . 
C35 C 0.8639(2) 0.2189(2) 0.53820(16) 0.0289(6) Uani 1 1 d . . . . . 
H35A H 0.9094 0.2270 0.4971 0.043 Uiso 1 1 calc R U . . . 
H35B H 0.8620 0.2824 0.5652 0.043 Uiso 1 1 calc R U . . . 
H35C H 0.7941 0.2019 0.5221 0.043 Uiso 1 1 calc R U . . . 
C36 C 0.8124(2) -0.1471(2) 0.55156(15) 0.0238(6) Uani 1 1 d . . . . . 
H36A H 0.8289 -0.2146 0.5329 0.036 Uiso 1 1 calc R U . . . 
H36B H 0.8164 -0.0971 0.5133 0.036 Uiso 1 1 calc R U . . . 
H36C H 0.7424 -0.1475 0.5714 0.036 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 C22 1.371(3) . ? 
O1 C21 1.448(3) . ? 
O2 C28 1.215(3) . ? 
O3 C29 1.315(3) . ? 
O3 C30 1.494(3) . ? 
O4 C29 1.200(4) . ? 
O5 C34 1.338(3) . ? 
O5 C2 1.455(3) . ? 
O6 C34 1.213(3) . ? 
O7 C10 1.370(3) . ? 
O7 H7 0.80(2) . ? 
C1 C18 1.498(4) . ? 
C1 C2 1.539(4) . ? 
C1 C17 1.566(3) . ? 
C1 H1A 1.0000 . ? 
C2 C3 1.535(3) . ? 
C2 H2A 1.0000 . ? 
C3 C4 1.523(4) . ? 
C3 C36 1.534(4) . ? 
C3 C16 1.541(3) . ? 
C4 C5 1.542(3) . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C5 C6 1.540(3) . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 C7 1.524(3) . ? 
C6 C15 1.537(3) . ? 
C6 H6A 1.0000 . ? 
C7 C8 1.394(4) . ? 
C7 C12 1.408(3) . ? 
C8 C9 1.385(4) . ? 
C8 H8A 0.9500 . ? 
C9 C10 1.393(4) . ? 
C9 H9A 0.9500 . ? 
C10 C11 1.383(4) . ? 
C11 C12 1.402(4) . ? 
C11 H11A 0.9500 . ? 
C12 C13 1.515(4) . ? 
C13 C14 1.523(4) . ? 
C13 H13A 0.9900 . ? 
C13 H13B 0.9900 . ? 
C14 C15 1.527(3) . ? 
C14 H14A 0.9900 . ? 
C14 H14B 0.9900 . ? 
C15 C16 1.520(3) . ? 
C15 H15A 1.0000 . ? 
C16 C17 1.539(4) . ? 
C16 H16A 1.0000 . ? 
C17 H17A 0.9900 . ? 
C17 H17B 0.9900 . ? 
C18 C19 1.322(4) . ? 
C18 H18A 0.9500 . ? 
C19 C20 1.497(4) . ? 
C19 H19A 0.9500 . ? 
C20 C21 1.527(3) . ? 
C20 H20A 0.9900 . ? 
C20 H20B 0.9900 . ? 
C21 C29 1.535(4) . ? 
C21 C28 1.550(4) . ? 
C22 C23 1.381(4) . ? 
C22 C27 1.391(4) . ? 
C23 C24 1.381(4) . ? 
C23 H23A 0.9500 . ? 
C24 C25 1.399(5) . ? 
C24 H24A 0.9500 . ? 
C25 C26 1.381(4) . ? 
C25 H25A 0.9500 . ? 
C26 C27 1.392(4) . ? 
C26 H26A 0.9500 . ? 
C27 C28 1.460(4) . ? 
C30 C32A 1.447(10) . ? 
C30 C33 1.470(9) . ? 
C30 C31 1.477(6) . ? 
C30 C33A 1.557(12) . ? 
C30 C32 1.578(7) . ? 
C30 C31A 1.588(9) . ? 
C31 H31A 0.9800 . ? 
C31 H31B 0.9800 . ? 
C31 H31C 0.9800 . ? 
C32 H32A 0.9800 . ? 
C32 H32B 0.9800 . ? 
C32 H32C 0.9800 . ? 
C33 H33A 0.9800 . ? 
C33 H33B 0.9800 . ? 
C33 H33C 0.9800 . ? 
C31A H31D 0.9800 . ? 
C31A H31E 0.9800 . ? 
C31A H31F 0.9800 . ? 
C32A H32D 0.9800 . ? 
C32A H32E 0.9800 . ? 
C32A H32F 0.9800 . ? 
C33A H33D 0.9800 . ? 
C33A H33E 0.9800 . ? 
C33A H33F 0.9800 . ? 
C34 C35 1.499(4) . ? 
C35 H35A 0.9800 . ? 
C35 H35B 0.9800 . ? 
C35 H35C 0.9800 . ? 
C36 H36A 0.9800 . ? 
C36 H36B 0.9800 . ? 
C36 H36C 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 
C22 O1 C21 108.2(2) . . ? 
C29 O3 C30 121.3(2) . . ? 
C34 O5 C2 118.1(2) . . ? 
C10 O7 H7 111(3) . . ? 
C18 C1 C2 111.5(2) . . ? 
C18 C1 C17 114.6(2) . . ? 
C2 C1 C17 103.5(2) . . ? 
C18 C1 H1A 109.0 . . ? 
C2 C1 H1A 109.0 . . ? 
C17 C1 H1A 109.0 . . ? 
O5 C2 C3 114.7(2) . . ? 
O5 C2 C1 108.6(2) . . ? 
C3 C2 C1 105.3(2) . . ? 
O5 C2 H2A 109.3 . . ? 
C3 C2 H2A 109.3 . . ? 
C1 C2 H2A 109.3 . . ? 
C4 C3 C36 110.7(2) . . ? 
C4 C3 C2 116.3(2) . . ? 
C36 C3 C2 109.8(2) . . ? 
C4 C3 C16 108.4(2) . . ? 
C36 C3 C16 113.6(2) . . ? 
C2 C3 C16 97.46(19) . . ? 
C3 C4 C5 111.2(2) . . ? 
C3 C4 H4A 109.4 . . ? 
C5 C4 H4A 109.4 . . ? 
C3 C4 H4B 109.4 . . ? 
C5 C4 H4B 109.4 . . ? 
H4A C4 H4B 108.0 . . ? 
C6 C5 C4 111.7(2) . . ? 
C6 C5 H5A 109.3 . . ? 
C4 C5 H5A 109.3 . . ? 
C6 C5 H5B 109.3 . . ? 
C4 C5 H5B 109.3 . . ? 
H5A C5 H5B 107.9 . . ? 
C7 C6 C15 110.8(2) . . ? 
C7 C6 C5 113.6(2) . . ? 
C15 C6 C5 112.4(2) . . ? 
C7 C6 H6A 106.5 . . ? 
C15 C6 H6A 106.5 . . ? 
C5 C6 H6A 106.5 . . ? 
C8 C7 C12 117.7(2) . . ? 
C8 C7 C6 120.9(2) . . ? 
C12 C7 C6 121.4(2) . . ? 
C9 C8 C7 122.6(2) . . ? 
C9 C8 H8A 118.7 . . ? 
C7 C8 H8A 118.7 . . ? 
C8 C9 C10 119.3(2) . . ? 
C8 C9 H9A 120.4 . . ? 
C10 C9 H9A 120.4 . . ? 
O7 C10 C11 123.3(2) . . ? 
O7 C10 C9 117.3(2) . . ? 
C11 C10 C9 119.4(2) . . ? 
C10 C11 C12 121.4(2) . . ? 
C10 C11 H11A 119.3 . . ? 
C12 C11 H11A 119.3 . . ? 
C11 C12 C7 119.6(2) . . ? 
C11 C12 C13 118.9(2) . . ? 
C7 C12 C13 121.5(2) . . ? 
C12 C13 C14 113.5(2) . . ? 
C12 C13 H13A 108.9 . . ? 
C14 C13 H13A 108.9 . . ? 
C12 C13 H13B 108.9 . . ? 
C14 C13 H13B 108.9 . . ? 
H13A C13 H13B 107.7 . . ? 
C13 C14 C15 110.1(2) . . ? 
C13 C14 H14A 109.6 . . ? 
C15 C14 H14A 109.6 . . ? 
C13 C14 H14B 109.6 . . ? 
C15 C14 H14B 109.6 . . ? 
H14A C14 H14B 108.2 . . ? 
C16 C15 C14 112.9(2) . . ? 
C16 C15 C6 108.52(19) . . ? 
C14 C15 C6 108.6(2) . . ? 
C16 C15 H15A 108.9 . . ? 
C14 C15 H15A 108.9 . . ? 
C6 C15 H15A 108.9 . . ? 
C15 C16 C17 119.6(2) . . ? 
C15 C16 C3 112.5(2) . . ? 
C17 C16 C3 104.73(19) . . ? 
C15 C16 H16A 106.4 . . ? 
C17 C16 H16A 106.4 . . ? 
C3 C16 H16A 106.4 . . ? 
C16 C17 C1 104.5(2) . . ? 
C16 C17 H17A 110.8 . . ? 
C1 C17 H17A 110.8 . . ? 
C16 C17 H17B 110.8 . . ? 
C1 C17 H17B 110.8 . . ? 
H17A C17 H17B 108.9 . . ? 
C19 C18 C1 125.3(3) . . ? 
C19 C18 H18A 117.3 . . ? 
C1 C18 H18A 117.3 . . ? 
C18 C19 C20 122.9(3) . . ? 
C18 C19 H19A 118.5 . . ? 
C20 C19 H19A 118.5 . . ? 
C19 C20 C21 113.5(2) . . ? 
C19 C20 H20A 108.9 . . ? 
C21 C20 H20A 108.9 . . ? 
C19 C20 H20B 108.9 . . ? 
C21 C20 H20B 108.9 . . ? 
H20A C20 H20B 107.7 . . ? 
O1 C21 C20 110.6(2) . . ? 
O1 C21 C29 107.6(2) . . ? 
C20 C21 C29 111.2(2) . . ? 
O1 C21 C28 105.1(2) . . ? 
C20 C21 C28 113.2(2) . . ? 
C29 C21 C28 108.8(2) . . ? 
O1 C22 C23 124.2(3) . . ? 
O1 C22 C27 113.6(2) . . ? 
C23 C22 C27 122.2(3) . . ? 
C22 C23 C24 116.9(3) . . ? 
C22 C23 H23A 121.5 . . ? 
C24 C23 H23A 121.5 . . ? 
C23 C24 C25 122.0(3) . . ? 
C23 C24 H24A 119.0 . . ? 
C25 C24 H24A 119.0 . . ? 
C26 C25 C24 120.4(3) . . ? 
C26 C25 H25A 119.8 . . ? 
C24 C25 H25A 119.8 . . ? 
C25 C26 C27 118.1(3) . . ? 
C25 C26 H26A 120.9 . . ? 
C27 C26 H26A 120.9 . . ? 
C22 C27 C26 120.4(3) . . ? 
C22 C27 C28 107.4(2) . . ? 
C26 C27 C28 132.2(3) . . ? 
O2 C28 C27 130.4(3) . . ? 
O2 C28 C21 124.6(2) . . ? 
C27 C28 C21 105.0(2) . . ? 
O4 C29 O3 127.0(3) . . ? 
O4 C29 C21 122.9(2) . . ? 
O3 C29 C21 110.2(2) . . ? 
C33 C30 C31 117.8(4) . . ? 
C32A C30 O3 106.8(5) . . ? 
C33 C30 O3 113.1(4) . . ? 
C31 C30 O3 107.3(3) . . ? 
C32A C30 C33A 114.5(7) . . ? 
O3 C30 C33A 104.8(5) . . ? 
C33 C30 C32 106.9(5) . . ? 
C31 C30 C32 110.7(4) . . ? 
O3 C30 C32 99.5(3) . . ? 
C32A C30 C31A 114.7(5) . . ? 
O3 C30 C31A 110.4(4) . . ? 
C33A C30 C31A 105.1(6) . . ? 
C30 C31 H31A 109.5 . . ? 
C30 C31 H31B 109.5 . . ? 
H31A C31 H31B 109.5 . . ? 
C30 C31 H31C 109.5 . . ? 
H31A C31 H31C 109.5 . . ? 
H31B C31 H31C 109.5 . . ? 
C30 C32 H32A 109.5 . . ? 
C30 C32 H32B 109.5 . . ? 
H32A C32 H32B 109.5 . . ? 
C30 C32 H32C 109.5 . . ? 
H32A C32 H32C 109.5 . . ? 
H32B C32 H32C 109.5 . . ? 
C30 C33 H33A 109.5 . . ? 
C30 C33 H33B 109.5 . . ? 
H33A C33 H33B 109.5 . . ? 
C30 C33 H33C 109.5 . . ? 
H33A C33 H33C 109.5 . . ? 
H33B C33 H33C 109.5 . . ? 
C30 C31A H31D 109.5 . . ? 
C30 C31A H31E 109.5 . . ? 
H31D C31A H31E 109.5 . . ? 
C30 C31A H31F 109.5 . . ? 
H31D C31A H31F 109.5 . . ? 
H31E C31A H31F 109.5 . . ? 
C30 C32A H32D 109.5 . . ? 
C30 C32A H32E 109.5 . . ? 
H32D C32A H32E 109.5 . . ? 
C30 C32A H32F 109.5 . . ? 
H32D C32A H32F 109.5 . . ? 
H32E C32A H32F 109.5 . . ? 
C30 C33A H33D 109.5 . . ? 
C30 C33A H33E 109.5 . . ? 
H33D C33A H33E 109.5 . . ? 
C30 C33A H33F 109.5 . . ? 
H33D C33A H33F 109.5 . . ? 
H33E C33A H33F 109.5 . . ? 
O6 C34 O5 123.6(2) . . ? 
O6 C34 C35 124.2(2) . . ? 
O5 C34 C35 112.2(2) . . ? 
C34 C35 H35A 109.5 . . ? 
C34 C35 H35B 109.5 . . ? 
H35A C35 H35B 109.5 . . ? 
C34 C35 H35C 109.5 . . ? 
H35A C35 H35C 109.5 . . ? 
H35B C35 H35C 109.5 . . ? 
C3 C36 H36A 109.5 . . ? 
C3 C36 H36B 109.5 . . ? 
H36A C36 H36B 109.5 . . ? 
C3 C36 H36C 109.5 . . ? 
H36A C36 H36C 109.5 . . ? 
H36B C36 H36C 109.5 . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C34 O5 C2 C3 -103.2(3) . . . . ? 
C34 O5 C2 C1 139.3(2) . . . . ? 
C18 C1 C2 O5 -82.8(2) . . . . ? 
C17 C1 C2 O5 153.46(19) . . . . ? 
C18 C1 C2 C3 153.9(2) . . . . ? 
C17 C1 C2 C3 30.1(3) . . . . ? 
O5 C2 C3 C4 78.8(3) . . . . ? 
C1 C2 C3 C4 -161.8(2) . . . . ? 
O5 C2 C3 C36 -47.9(3) . . . . ? 
C1 C2 C3 C36 71.4(2) . . . . ? 
O5 C2 C3 C16 -166.3(2) . . . . ? 
C1 C2 C3 C16 -47.0(2) . . . . ? 
C36 C3 C4 C5 -68.2(3) . . . . ? 
C2 C3 C4 C5 165.5(2) . . . . ? 
C16 C3 C4 C5 57.0(3) . . . . ? 
C3 C4 C5 C6 -54.3(3) . . . . ? 
C4 C5 C6 C7 179.7(2) . . . . ? 
C4 C5 C6 C15 52.9(3) . . . . ? 
C15 C6 C7 C8 159.4(2) . . . . ? 
C5 C6 C7 C8 31.7(3) . . . . ? 
C15 C6 C7 C12 -22.8(3) . . . . ? 
C5 C6 C7 C12 -150.5(2) . . . . ? 
C12 C7 C8 C9 0.6(4) . . . . ? 
C6 C7 C8 C9 178.4(2) . . . . ? 
C7 C8 C9 C10 0.0(4) . . . . ? 
C8 C9 C10 O7 -179.9(2) . . . . ? 
C8 C9 C10 C11 0.0(4) . . . . ? 
O7 C10 C11 C12 179.4(3) . . . . ? 
C9 C10 C11 C12 -0.6(4) . . . . ? 
C10 C11 C12 C7 1.1(4) . . . . ? 
C10 C11 C12 C13 -179.4(2) . . . . ? 
C8 C7 C12 C11 -1.1(4) . . . . ? 
C6 C7 C12 C11 -178.9(2) . . . . ? 
C8 C7 C12 C13 179.4(2) . . . . ? 
C6 C7 C12 C13 1.6(4) . . . . ? 
C11 C12 C13 C14 168.0(2) . . . . ? 
C7 C12 C13 C14 -12.5(4) . . . . ? 
C12 C13 C14 C15 44.7(3) . . . . ? 
C13 C14 C15 C16 172.9(2) . . . . ? 
C13 C14 C15 C6 -66.7(3) . . . . ? 
C7 C6 C15 C16 177.4(2) . . . . ? 
C5 C6 C15 C16 -54.3(3) . . . . ? 
C7 C6 C15 C14 54.3(3) . . . . ? 
C5 C6 C15 C14 -177.4(2) . . . . ? 
C14 C15 C16 C17 -56.8(3) . . . . ? 
C6 C15 C16 C17 -177.2(2) . . . . ? 
C14 C15 C16 C3 179.7(2) . . . . ? 
C6 C15 C16 C3 59.2(3) . . . . ? 
C4 C3 C16 C15 -61.2(3) . . . . ? 
C36 C3 C16 C15 62.3(3) . . . . ? 
C2 C3 C16 C15 177.8(2) . . . . ? 
C4 C3 C16 C17 167.3(2) . . . . ? 
C36 C3 C16 C17 -69.2(3) . . . . ? 
C2 C3 C16 C17 46.3(2) . . . . ? 
C15 C16 C17 C1 -156.4(2) . . . . ? 
C3 C16 C17 C1 -29.2(2) . . . . ? 
C18 C1 C17 C16 -122.1(2) . . . . ? 
C2 C1 C17 C16 -0.4(3) . . . . ? 
C2 C1 C18 C19 117.9(3) . . . . ? 
C17 C1 C18 C19 -124.9(3) . . . . ? 
C1 C18 C19 C20 -177.9(2) . . . . ? 
C18 C19 C20 C21 125.2(3) . . . . ? 
C22 O1 C21 C20 -130.7(2) . . . . ? 
C22 O1 C21 C29 107.8(2) . . . . ? 
C22 O1 C21 C28 -8.1(2) . . . . ? 
C19 C20 C21 O1 73.5(3) . . . . ? 
C19 C20 C21 C29 -167.0(2) . . . . ? 
C19 C20 C21 C28 -44.1(3) . . . . ? 
C21 O1 C22 C23 -173.0(2) . . . . ? 
C21 O1 C22 C27 6.8(3) . . . . ? 
O1 C22 C23 C24 -180.0(2) . . . . ? 
C27 C22 C23 C24 0.3(4) . . . . ? 
C22 C23 C24 C25 1.1(4) . . . . ? 
C23 C24 C25 C26 -1.5(5) . . . . ? 
C24 C25 C26 C27 0.4(5) . . . . ? 
O1 C22 C27 C26 178.9(2) . . . . ? 
C23 C22 C27 C26 -1.3(4) . . . . ? 
O1 C22 C27 C28 -2.1(3) . . . . ? 
C23 C22 C27 C28 177.6(2) . . . . ? 
C25 C26 C27 C22 0.9(4) . . . . ? 
C25 C26 C27 C28 -177.7(3) . . . . ? 
C22 C27 C28 O2 177.5(3) . . . . ? 
C26 C27 C28 O2 -3.8(5) . . . . ? 
C22 C27 C28 C21 -3.0(3) . . . . ? 
C26 C27 C28 C21 175.7(3) . . . . ? 
O1 C21 C28 O2 -173.7(2) . . . . ? 
C20 C21 C28 O2 -52.9(4) . . . . ? 
C29 C21 C28 O2 71.2(3) . . . . ? 
O1 C21 C28 C27 6.8(3) . . . . ? 
C20 C21 C28 C27 127.6(2) . . . . ? 
C29 C21 C28 C27 -108.3(2) . . . . ? 
C30 O3 C29 O4 -4.8(5) . . . . ? 
C30 O3 C29 C21 175.6(2) . . . . ? 
O1 C21 C29 O4 128.3(3) . . . . ? 
C20 C21 C29 O4 7.1(4) . . . . ? 
C28 C21 C29 O4 -118.3(3) . . . . ? 
O1 C21 C29 O3 -52.1(3) . . . . ? 
C20 C21 C29 O3 -173.3(2) . . . . ? 
C28 C21 C29 O3 61.3(3) . . . . ? 
C29 O3 C30 C32A -170.2(5) . . . . ? 
C29 O3 C30 C33 60.2(5) . . . . ? 
C29 O3 C30 C31 -71.3(4) . . . . ? 
C29 O3 C30 C33A 67.8(7) . . . . ? 
C29 O3 C30 C32 173.3(3) . . . . ? 
C29 O3 C30 C31A -44.9(5) . . . . ? 
C2 O5 C34 O6 6.1(4) . . . . ? 
C2 O5 C34 C35 -174.1(2) . . . . ? 
 
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 
O7 H7 O6  0.80(2) 1.99(2) 2.782(3) 168(4) 1_545 
 
_refine_diff_density_max    0.293 
_refine_diff_density_min   -0.328 
_refine_diff_density_rms    0.079 
 
 
 
_publ_requested_category         FO 
 
_publ_section_references 
; 
Bruker (2014). APEX2. Bruker AXS, Inc., Madison, Wisconsin, USA. 
 
Bruker (2014). SAINT, SHELXTL, XCIF, XPREP.  Bruker AXS, Inc., Madison, 
Wisconsin, USA. 
 
Bruker (2014).  SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. 
 
CrystalMaker (1994).  CrystalMaker, a crystal and molecular structures 
program for Mac and Windows. CrystalMaker Software Ltd., Oxford, England 
(www.crystalmaker.com). 
 
Flack, H. D. (1983), Acta Cryst. A39, 876-881. 
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst., 33, 1143-1148. 
 
Hamilton, W.C. and Ibers, J.A. (1968). Hydrogen 
Bonding in Solids.  W.A.Benjamin, Inc., New York, New York, USA. 
 
Hooft,R.; Straver, L.; Spek, A. (2008). J. 
Appl. Cryst. 41, 96-103. 
 
Hubschle, C. B., Sheldrick,G. M., Dittrich, B. (2011). 
J. Appl. Cryst., 44, 1281-1284. 
 
Spek,A.L. (2009). Acta Cryst. D65, 148-155. 
 
Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8. 
 
Sheldrick, G.M. (2015). Acta Cryst.<ι> A71<β>, 3-8. 
 
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. 
 
; 
 
_publ_section_figure_captions 
; 
Figure 1.  SHELXTL (Bruker, 2014) plot showing 35% probability ellipsoids 
for non-H atoms and circles of arbitrary size for H atoms. 
; 
 
_publ_section_exptl_prep 
; 
Crystals were grown from diethyl ether. 
; 
 
_publ_section_exptl_refinement 
; 
A structural model consisting of one target molecule in the asymmetric unit 
was developed. The t-butyl group was found to be disordered over two 
orientations. The C---C bond distances of the disordered t-butyl group were 
restrained to be similar (esd 0.02). The angles between the methyl carbon 
atoms of the t-butyl group were also restrained to be similar (esd 0.04). 
Due to the close proximity of the two orientations, the displacement 
parameters of the disordered carbon atoms were constrained to be equal. 
The site occupancy ratio of the two orientations was allowed to freely refine 
and converged to 0.609(8):0.391(8). 
 
H atom treatment - Methyl H atom positions, R-CH₃, were optimized by 
rotation about R-C bonds with idealized C-H, R--H and H--H distances. 
The hydroxyl H atom was located in the difference map. The O---H distance 
was restrained to 0.84(2) Å; the H atom position was then allowed to freely 
refine. At convergence, the O---H proton was located in a good hydrogen 
bonding position (Hamilton & Ibers, 1968). 
Remaining H atoms were included as riding idealized 
contributors.  Methyl and hydroxyl H atom U's were assigned as 
1.5 times Ueq of the carrier atom; remaining H atom U's were 
assigned as 1.2 times carrier Ueq. On the basis of 2578 unmerged 
Friedel opposites, the fractional contribution of the racemic twin was 
negligible (Flack, 1983; Flack & Bernardinelli, 2000). The absolute structure 
parameter y was calculated using PLATON (Spek, 2009). The resulting value was 
y=0.08(7) indicating that the absolute structure has probably been 
determined correctly (Hooft, Straver and Spek 2008). 
; 
 
_publ_contact_author 
; 
M. Christina White 
University of Illinois 
Department of Chemistry 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
; 
_publ_contact_author_phone        '1  217 333 6173'  
_publ_contact_author_email        'mcwhite7@illinois.edu' 
_publ_contact_letter 
; 
 ? 
; 
_publ_requested_journal           'Journal of American Chemical society' 
_publ_requested_coeditor_name     ? 
 
_publ_section_title 
; 
 ? 
; 
 
_publ_section_abstract 
; 
 ? 
; 
 
_publ_section_comment 
; 
 ? 
; 
 
_publ_section_acknowledgements 
; 
Financial support for this work was provided by 
the NIGMS MIRA (R35 GM122525).
; 
 
loop_ 
 _publ_author_name 
 _publ_author_address 
'Liu, Wei' 
; 
University of Illinois 
Department of Chemistry 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
; 
'Ali, Siraj Z.' 
; 
University of Illinois 
Department of Chemistry 
600 South Mathews Avenue  
Urbana, Illinois  61801 
USA 
; 
'Ammann, Stephen E.' 
; 
University of Illinois 
Department of Chemistry 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
; 
'White, M. Christina' 
; 
University of Illinois 
Department of Chemistry 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
; 
 
 
loop_ 
 _exptl_crystal_face_index_h 
 _exptl_crystal_face_index_k 
 _exptl_crystal_face_index_l 
 _exptl_crystal_face_perp_dist 
    0.00    1.00    0.00    0.1770 
    0.00   -1.00    0.00    0.1260 
    1.00    0.00   -2.00    0.0560 
    2.00    0.00    1.00    0.0670 
   -2.00    0.00    1.00    0.0570 
    1.00    1.00   -6.00    0.0710 

# start Validation Reply Form
_vrf_PLAT934_dd27esa
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check 
RESPONSE: These two reflections were very intense reflections that saturated
the detector during the normal data collection runs, so they were replaced
by reflections from the fast scan. The reflections were partially obscured by
the beam stop in the fast scan, but since the (Iobs-Icalc)/SigmaW was exactly
10 they were retained in the final refinement.
;
# end Validation Reply Form


