# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 960227'
_audit_update_record             
;
2016-08-15 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(2S,4R,5R)-5-Hydroxy-3-oxo-4-(pent-4-enyl)eicosan-2-yl
_chemical_name_common            ?
_chemical_melting_point          62-64
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H56 O5'
_chemical_formula_weight         532.77

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   12.8359(8)
_cell_length_b                   4.9611(2)
_cell_length_c                   26.2020(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.210(6)
_cell_angle_gamma                90
_cell_volume                     1655.35(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    130.0(2)
_cell_measurement_reflns_used    2850
_cell_measurement_theta_min      3.3976
_cell_measurement_theta_max      74.2580

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.069
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6424
_exptl_crystal_size_mid          0.1285
_exptl_crystal_size_min          0.0455
_exptl_absorpt_coefficient_mu    0.547
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.60291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11321
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.400
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_full        67.496
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             5581
_reflns_number_gt                4301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_max     0.857
_reflns_Friedel_fraction_full    0.857

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1292P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1287 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5581
_refine_ls_number_parameters     346
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2006
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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
C1 C 0.9701(3) 1.5282(10) 0.93005(19) 0.0415(11) Uani 1 1 d . . . . .
H1A H 1.0042 1.6464 0.9083 0.062 Uiso 1 1 calc R U . . .
H2A H 0.9515 1.6272 0.9590 0.062 Uiso 1 1 calc R U . . .
H3A H 1.0169 1.3840 0.9419 0.062 Uiso 1 1 calc R U . . .
C2 C 0.8716(3) 1.4124(9) 0.89976(16) 0.0318(9) Uani 1 1 d . . . . .
H1 H 0.8226 1.5581 0.8884 0.038 Uiso 1 1 calc R U . . .
C3 C 0.8962(3) 1.2472(9) 0.85328(16) 0.0318(9) Uani 1 1 d . . . . .
C4 C 0.9300(3) 1.3956(8) 0.80679(17) 0.0338(9) Uani 1 1 d . . . . .
H4 H 0.9466 1.5833 0.8162 0.041 Uiso 1 1 calc R U . . .
C5 C 1.0288(3) 1.2555(9) 0.79263(15) 0.0294(8) Uani 1 1 d . . . . .
H5 H 1.0116 1.0676 0.7836 0.035 Uiso 1 1 calc R U . . .
C6 C 1.0743(3) 1.3887(8) 0.74765(16) 0.0303(9) Uani 1 1 d . . . . .
H6A H 1.0205 1.3942 0.7181 0.036 Uiso 1 1 calc R U . . .
H6B H 1.0933 1.5732 0.7569 0.036 Uiso 1 1 calc R U . . .
C7 C 1.1707(3) 1.2428(9) 0.73249(16) 0.0314(9) Uani 1 1 d . . . . .
H7A H 1.2242 1.2348 0.7621 0.038 Uiso 1 1 calc R U . . .
H7B H 1.1515 1.0594 0.7226 0.038 Uiso 1 1 calc R U . . .
C8 C 1.2162(3) 1.3805(9) 0.68831(16) 0.0311(9) Uani 1 1 d . . . . .
H8A H 1.2350 1.5642 0.6982 0.037 Uiso 1 1 calc R U . . .
H8B H 1.1626 1.3881 0.6587 0.037 Uiso 1 1 calc R U . . .
C9 C 1.3125(3) 1.2376(9) 0.67298(15) 0.0297(8) Uani 1 1 d . . . . .
H9A H 1.3655 1.2284 0.7028 0.036 Uiso 1 1 calc R U . . .
H9B H 1.2932 1.0543 0.6630 0.036 Uiso 1 1 calc R U . . .
C10 C 1.3599(3) 1.3719(9) 0.62930(16) 0.0291(8) Uani 1 1 d . . . . .
H10A H 1.3769 1.5573 0.6387 0.035 Uiso 1 1 calc R U . . .
H10B H 1.3081 1.3745 0.5990 0.035 Uiso 1 1 calc R U . . .
C11 C 1.4586(3) 1.2318(9) 0.61601(16) 0.0294(8) Uani 1 1 d . . . . .
H11A H 1.4400 1.0522 0.6034 0.035 Uiso 1 1 calc R U . . .
H11B H 1.5075 1.2126 0.6472 0.035 Uiso 1 1 calc R U . . .
C12 C 1.5135(3) 1.3796(9) 0.57585(17) 0.0311(9) Uani 1 1 d . . . . .
H12A H 1.5318 1.5596 0.5883 0.037 Uiso 1 1 calc R U . . .
H12B H 1.4649 1.3974 0.5445 0.037 Uiso 1 1 calc R U . . .
C13 C 1.6130(3) 1.2379(9) 0.56314(16) 0.0312(9) Uani 1 1 d . . . . .
H13A H 1.6625 1.2252 0.5942 0.037 Uiso 1 1 calc R U . . .
H13B H 1.5951 1.0560 0.5516 0.037 Uiso 1 1 calc R U . . .
C14 C 1.6651(3) 1.3812(9) 0.52215(17) 0.0314(9) Uani 1 1 d . . . . .
H14A H 1.6836 1.5623 0.5340 0.038 Uiso 1 1 calc R U . . .
H14B H 1.6149 1.3966 0.4913 0.038 Uiso 1 1 calc R U . . .
C15 C 1.7634(3) 1.2409(9) 0.50834(15) 0.0290(8) Uani 1 1 d . . . . .
H15A H 1.7456 1.0578 0.4976 0.035 Uiso 1 1 calc R U . . .
H15B H 1.8147 1.2314 0.5388 0.035 Uiso 1 1 calc R U . . .
C16 C 1.8132(3) 1.3822(9) 0.46557(16) 0.0303(9) Uani 1 1 d . . . . .
H16A H 1.8307 1.5656 0.4763 0.036 Uiso 1 1 calc R U . . .
H16B H 1.7619 1.3912 0.4351 0.036 Uiso 1 1 calc R U . . .
C17 C 1.9124(3) 1.2437(9) 0.45145(15) 0.0285(8) Uani 1 1 d . . . . .
H17A H 1.9639 1.2350 0.4818 0.034 Uiso 1 1 calc R U . . .
H17B H 1.8950 1.0603 0.4407 0.034 Uiso 1 1 calc R U . . .
C18 C 1.9608(3) 1.3845(8) 0.40915(16) 0.0303(9) Uani 1 1 d . . . . .
H18A H 1.9771 1.5688 0.4197 0.036 Uiso 1 1 calc R U . . .
H18B H 1.9095 1.3911 0.3787 0.036 Uiso 1 1 calc R U . . .
C19 C 2.0601(3) 1.2517(9) 0.39521(16) 0.0344(9) Uani 1 1 d . . . . .
H19A H 2.1114 1.2434 0.4257 0.041 Uiso 1 1 calc R U . . .
H19B H 2.0439 1.0683 0.3841 0.041 Uiso 1 1 calc R U . . .
C20 C 2.1076(4) 1.3994(11) 0.35313(18) 0.0428(11) Uani 1 1 d . . . . .
H20A H 2.1698 1.3070 0.3459 0.064 Uiso 1 1 calc R U . . .
H20B H 2.0577 1.4049 0.3226 0.064 Uiso 1 1 calc R U . . .
H20C H 2.1253 1.5800 0.3642 0.064 Uiso 1 1 calc R U . . .
C21 C 0.8360(4) 1.3883(12) 0.76242(19) 0.0482(12) Uani 1 1 d . . . . .
H21A H 0.8598 1.4615 0.7316 0.058 Uiso 1 1 calc R U . . .
H21B H 0.8168 1.2016 0.7554 0.058 Uiso 1 1 calc R U . . .
C22 C 0.7395(4) 1.5394(11) 0.7726(2) 0.0482(12) Uani 1 1 d . . . . .
H22A H 0.7586 1.7252 0.7807 0.058 Uiso 1 1 calc R U . . .
H22B H 0.7136 1.4620 0.8026 0.058 Uiso 1 1 calc R U . . .
C23 C 0.6507(4) 1.5356(13) 0.7275(2) 0.0543(13) Uani 1 1 d . . . . .
H23A H 0.6795 1.5930 0.6967 0.065 Uiso 1 1 calc R U . . .
H23B H 0.6272 1.3508 0.7220 0.065 Uiso 1 1 calc R U . . .
C24 C 0.5593(4) 1.7025(13) 0.7331(2) 0.0618(16) Uani 1 1 d . . . . .
H24 H 0.5055 1.7009 0.7058 0.074 Uiso 1 1 calc R U . . .
C25 C 0.5444(5) 1.8581(17) 0.7735(3) 0.082(2) Uani 1 1 d . . . . .
H25A H 0.5957 1.8671 0.8018 0.098 Uiso 1 1 calc R U . . .
H25B H 0.4827 1.9570 0.7731 0.098 Uiso 1 1 calc R U . . .
C26 C 0.7313(3) 1.1336(8) 0.91870(17) 0.0304(9) Uani 1 1 d . . . . .
C27 C 0.6990(3) 0.9349(8) 0.95586(17) 0.0307(9) Uani 1 1 d . . . . .
C28 C 0.6138(3) 0.7693(9) 0.94040(17) 0.0353(9) Uani 1 1 d . . . . .
H28 H 0.5771 0.7884 0.9077 0.042 Uiso 1 1 calc R U . . .
C29 C 0.5833(4) 0.5743(9) 0.9738(2) 0.0405(11) Uani 1 1 d . . . . .
H29 H 0.5264 0.4628 0.9632 0.049 Uiso 1 1 calc R U . . .
C30 C 0.6366(4) 0.5465(10) 1.0219(2) 0.0446(12) Uani 1 1 d . . . . .
H30 H 0.6160 0.4160 1.0440 0.053 Uiso 1 1 calc R U . . .
C31 C 0.7214(4) 0.7120(11) 1.0379(2) 0.0467(12) Uani 1 1 d . . . . .
H31 H 0.7576 0.6911 1.0707 0.056 Uiso 1 1 calc R U . . .
C32 C 0.7528(3) 0.9088(10) 1.00540(18) 0.0397(10) Uani 1 1 d . . . . .
H32 H 0.8089 1.0219 1.0164 0.048 Uiso 1 1 calc R U . . .
C33 C 1.3041(5) 0.7391(18) 0.8430(3) 0.0810(19) Uani 1 1 d . . . . .
H33A H 1.3017 0.6986 0.8071 0.122 Uiso 1 1 calc R U . . .
H33B H 1.3397 0.5965 0.8630 0.122 Uiso 1 1 calc R U . . .
H33C H 1.3410 0.9055 0.8505 0.122 Uiso 1 1 calc R U . . .
O1 O 0.8264(2) 1.2394(6) 0.93523(10) 0.0322(6) Uani 1 1 d . . . . .
O2 O 0.6809(2) 1.1946(7) 0.87872(12) 0.0386(7) Uani 1 1 d . . . . .
O3 O 0.8883(3) 1.0040(7) 0.85317(13) 0.0446(8) Uani 1 1 d . . . . .
O4 O 1.1059(2) 1.2595(6) 0.83754(11) 0.0346(6) Uani 1 1 d . . . . .
H4A H 1.1469 1.1336 0.8362 0.052 Uiso 1 1 calc R U . . .
O5 O 1.1958(3) 0.7647(7) 0.85626(15) 0.0505(9) Uani 1 1 d . . . . .
H5A H 1.1637 0.6241 0.8491 0.076 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
C1 C2 1.518(6) . ?
C1 H1A 0.9600 . ?
C1 H2A 0.9600 . ?
C1 H3A 0.9600 . ?
C2 O1 1.440(5) . ?
C2 C3 1.533(6) . ?
C2 H1 0.9800 . ?
C3 O3 1.210(6) . ?
C3 C4 1.532(5) . ?
C4 C5 1.532(5) . ?
C4 C21 1.567(7) . ?
C4 H4 0.9800 . ?
C5 O4 1.439(5) . ?
C5 C6 1.530(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.529(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.522(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.522(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.516(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.523(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.526(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.530(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.512(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.525(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.528(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.532(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.508(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.519(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.514(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.500(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.537(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.458(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.342(9) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9300 . ?
C25 H25B 0.9300 . ?
C26 O2 1.199(5) . ?
C26 O1 1.350(5) . ?
C26 C27 1.481(6) . ?
C27 C28 1.386(6) . ?
C27 C32 1.398(6) . ?
C28 C29 1.393(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.364(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.386(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(6) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 O5 1.479(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O4 H4A 0.8200 . ?
O5 H5A 0.8200 . ?

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 C1 H1A 109.5 . . ?
C2 C1 H2A 109.5 . . ?
H1A C1 H2A 109.5 . . ?
C2 C1 H3A 109.5 . . ?
H1A C1 H3A 109.5 . . ?
H2A C1 H3A 109.5 . . ?
O1 C2 C1 105.4(3) . . ?
O1 C2 C3 109.5(3) . . ?
C1 C2 C3 112.1(3) . . ?
O1 C2 H1 109.9 . . ?
C1 C2 H1 109.9 . . ?
C3 C2 H1 109.9 . . ?
O3 C3 C4 120.6(4) . . ?
O3 C3 C2 120.6(4) . . ?
C4 C3 C2 118.8(4) . . ?
C3 C4 C5 107.5(3) . . ?
C3 C4 C21 108.1(3) . . ?
C5 C4 C21 113.2(4) . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C21 C4 H4 109.4 . . ?
O4 C5 C6 109.5(3) . . ?
O4 C5 C4 107.5(3) . . ?
C6 C5 C4 113.4(3) . . ?
O4 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
C4 C5 H5 108.8 . . ?
C7 C6 C5 113.3(3) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 112.7(3) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 113.2(3) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 114.3(3) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 113.4(3) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 114.1(3) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 113.6(3) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.2(3) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 114.0(3) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 113.6(3) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 114.1(3) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 113.6(3) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 114.3(3) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 113.1(4) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C4 115.6(4) . . ?
C22 C21 H21A 108.4 . . ?
C4 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C4 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 C23 113.9(5) . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 116.3(5) . . ?
C24 C23 H23A 108.2 . . ?
C22 C23 H23A 108.2 . . ?
C24 C23 H23B 108.2 . . ?
C22 C23 H23B 108.2 . . ?
H23A C23 H23B 107.4 . . ?
C25 C24 C23 127.1(5) . . ?
C25 C24 H24 116.5 . . ?
C23 C24 H24 116.5 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
O2 C26 O1 123.3(4) . . ?
O2 C26 C27 125.3(4) . . ?
O1 C26 C27 111.4(4) . . ?
C28 C27 C32 119.7(4) . . ?
C28 C27 C26 118.5(4) . . ?
C32 C27 C26 121.7(4) . . ?
C27 C28 C29 120.1(4) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 120.2(4) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.3(4) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 120.5(5) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C27 119.2(4) . . ?
C31 C32 H32 120.4 . . ?
C27 C32 H32 120.4 . . ?
O5 C33 H33A 109.5 . . ?
O5 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O5 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C26 O1 C2 116.5(3) . . ?
C5 O4 H4A 109.5 . . ?
C33 O5 H5A 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
O1 C2 C3 O3 -8.3(6) . . . . ?
C1 C2 C3 O3 108.3(5) . . . . ?
O1 C2 C3 C4 171.2(3) . . . . ?
C1 C2 C3 C4 -72.2(5) . . . . ?
O3 C3 C4 C5 -49.4(5) . . . . ?
C2 C3 C4 C5 131.1(4) . . . . ?
O3 C3 C4 C21 73.0(5) . . . . ?
C2 C3 C4 C21 -106.5(4) . . . . ?
C3 C4 C5 O4 -56.7(4) . . . . ?
C21 C4 C5 O4 -175.9(4) . . . . ?
C3 C4 C5 C6 -178.0(3) . . . . ?
C21 C4 C5 C6 62.8(5) . . . . ?
O4 C5 C6 C7 61.8(4) . . . . ?
C4 C5 C6 C7 -178.1(4) . . . . ?
C5 C6 C7 C8 -179.0(4) . . . . ?
C6 C7 C8 C9 179.8(4) . . . . ?
C7 C8 C9 C10 -179.5(3) . . . . ?
C8 C9 C10 C11 177.8(3) . . . . ?
C9 C10 C11 C12 -174.3(3) . . . . ?
C10 C11 C12 C13 179.5(3) . . . . ?
C11 C12 C13 C14 178.2(3) . . . . ?
C12 C13 C14 C15 -179.1(4) . . . . ?
C13 C14 C15 C16 178.0(3) . . . . ?
C14 C15 C16 C17 179.8(3) . . . . ?
C15 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 179.2(3) . . . . ?
C17 C18 C19 C20 -179.3(4) . . . . ?
C3 C4 C21 C22 65.3(5) . . . . ?
C5 C4 C21 C22 -175.8(4) . . . . ?
C4 C21 C22 C23 177.9(4) . . . . ?
C21 C22 C23 C24 -173.8(5) . . . . ?
C22 C23 C24 C25 -0.2(10) . . . . ?
O2 C26 C27 C28 12.3(6) . . . . ?
O1 C26 C27 C28 -167.4(4) . . . . ?
O2 C26 C27 C32 -168.6(4) . . . . ?
O1 C26 C27 C32 11.7(5) . . . . ?
C32 C27 C28 C29 -1.2(6) . . . . ?
C26 C27 C28 C29 178.0(4) . . . . ?
C27 C28 C29 C30 0.4(6) . . . . ?
C28 C29 C30 C31 0.1(7) . . . . ?
C29 C30 C31 C32 0.3(7) . . . . ?
C30 C31 C32 C27 -1.2(7) . . . . ?
C28 C27 C32 C31 1.6(6) . . . . ?
C26 C27 C32 C31 -177.6(4) . . . . ?
O2 C26 O1 C2 -6.5(6) . . . . ?
C27 C26 O1 C2 173.2(3) . . . . ?
C1 C2 O1 C26 173.3(4) . . . . ?
C3 C2 O1 C26 -65.9(4) . . . . ?

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
O5 H5A O4 0.82 1.96 2.778(5) 171.2 1_545

_refine_diff_density_max         0.692
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.057



