# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_cd213715
_database_code_depnum_ccdc_archive 'CCDC 1432825'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(3S,5S,8R,9S,10S,13R,14R,16R,17R)-16-hydroxy-10,17-dimethyl-17-((S)-1-((2R,5R)-5-methyl-6-oxotetrahydro-2H-pyran-2-yl)ethyl)tetradecahydro-15H-13,14-epoxycyclopenta[a]phenanthren-3-yl acetate'
_chemical_name_common            ?
_chemical_melting_point          173
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H44 O6'
_chemical_formula_weight         488.64

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                   9.9607(10)
_cell_length_b                   7.2910(8)
_cell_length_c                   18.5284(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.286(2)
_cell_angle_gamma                90.00
_cell_volume                     1339.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2864
_cell_measurement_theta_min      4.415
_cell_measurement_theta_max      56.330

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.117
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.68398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8136
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4763
_reflns_number_gt                4345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 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)+(0.0889P)²+0.2601P] where P=(Fo²+2Fc²)/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   -1.8(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4763
_refine_ls_number_parameters     368
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1516
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.005
_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 0.97194(18) 0.5946(3) 0.21793(10) 0.0424(4) Uani 1 1 d . . .
O2 O 0.9739(3) 0.8336(3) 0.33614(13) 0.0617(6) Uani 1 1 d . . .
H2 H 0.9267 0.8120 0.2985 0.093 Uiso 1 1 calc R . .
O3 O 0.6364(2) 0.3978(5) 0.3600(2) 0.1020(12) Uani 1 1 d . . .
O5 O 1.2707(3) 0.4176(4) -0.21490(13) 0.0753(8) Uani 1 1 d . . .
O6 O 1.3428(2) 0.1954(3) -0.13856(10) 0.0532(5) Uani 1 1 d . . .
C1 C 1.1542(3) 0.1352(4) 0.02509(16) 0.0470(7) Uani 1 1 d . . .
H1A H 1.1439 0.0250 0.0534 0.056 Uiso 1 1 calc R . .
H1B H 1.0647 0.1785 0.0082 0.056 Uiso 1 1 calc R . .
C2 C 1.2291(3) 0.0867(5) -0.04022(17) 0.0521(7) Uani 1 1 d . . .
H2A H 1.3145 0.0299 -0.0238 0.063 Uiso 1 1 calc R . .
H2B H 1.1765 -0.0014 -0.0701 0.063 Uiso 1 1 calc R . .
C3 C 1.2544(3) 0.2539(5) -0.08489(16) 0.0485(7) Uani 1 1 d . . .
H3 H 1.1691 0.2983 -0.1092 0.058 Uiso 1 1 calc R . .
C4 C 1.3216(3) 0.4048(5) -0.03968(15) 0.0465(7) Uani 1 1 d . . .
H4A H 1.3273 0.5137 -0.0693 0.056 Uiso 1 1 calc R . .
H4B H 1.4126 0.3678 -0.0228 0.056 Uiso 1 1 calc R . .
C5 C 1.2439(3) 0.4504(4) 0.02586(15) 0.0396(6) Uani 1 1 d . . .
H5 H 1.1531 0.4862 0.0059 0.048 Uiso 1 1 calc R . .
C6 C 1.3021(3) 0.6163(4) 0.06721(16) 0.0479(7) Uani 1 1 d . . .
H6A H 1.3929 0.5887 0.0879 0.057 Uiso 1 1 calc R . .
H6B H 1.3071 0.7186 0.0341 0.057 Uiso 1 1 calc R . .
C7 C 1.2161(3) 0.6691(4) 0.12707(16) 0.0465(7) Uani 1 1 d . . .
H7A H 1.1294 0.7132 0.1060 0.056 Uiso 1 1 calc R . .
H7B H 1.2596 0.7678 0.1555 0.056 Uiso 1 1 calc R . .
C8 C 1.1949(3) 0.5065(4) 0.17635(15) 0.0382(6) Uani 1 1 d . . .
H8 H 1.2842 0.4685 0.1978 0.046 Uiso 1 1 calc R . .
C9 C 1.1337(3) 0.3426(4) 0.13355(15) 0.0374(6) Uani 1 1 d . . .
H9 H 1.0487 0.3851 0.1082 0.045 Uiso 1 1 calc R . .
C10 C 1.2251(2) 0.2823(4) 0.07433(14) 0.0370(6) Uani 1 1 d . . .
C11 C 1.0973(3) 0.1930(4) 0.18667(15) 0.0462(7) Uani 1 1 d . . .
H11A H 1.1771 0.1605 0.2181 0.055 Uiso 1 1 calc R . .
H11B H 1.0672 0.0844 0.1596 0.055 Uiso 1 1 calc R . .
C12 C 0.9859(3) 0.2560(4) 0.23331(16) 0.0459(7) Uani 1 1 d . . .
H12A H 0.9005 0.2585 0.2036 0.055 Uiso 1 1 calc R . .
H12B H 0.9782 0.1679 0.2719 0.055 Uiso 1 1 calc R . .
C13 C 1.0130(2) 0.4423(4) 0.26581(14) 0.0371(6) Uani 1 1 d . . .
C14 C 1.1147(2) 0.5597(4) 0.23762(14) 0.0378(6) Uani 1 1 d . . .
C15 C 1.1723(3) 0.6869(5) 0.29612(15) 0.0486(7) Uani 1 1 d . . .
H15A H 1.1855 0.8087 0.2770 0.058 Uiso 1 1 calc R . .
H15B H 1.2579 0.6413 0.3183 0.058 Uiso 1 1 calc R . .
C16 C 1.0662(3) 0.6891(5) 0.35078(16) 0.0507(7) Uani 1 1 d . . .
H16 H 1.1118 0.7063 0.3995 0.061 Uiso 1 1 calc R . .
C17 C 1.0026(3) 0.4904(4) 0.34571(15) 0.0434(6) Uani 1 1 d . . .
C18 C 1.0961(3) 0.3607(5) 0.39128(17) 0.0554(8) Uani 1 1 d . . .
H18A H 1.0645 0.2369 0.3844 0.083 Uiso 1 1 calc R . .
H18B H 1.0967 0.3931 0.4415 0.083 Uiso 1 1 calc R . .
H18C H 1.1857 0.3704 0.3766 0.083 Uiso 1 1 calc R . .
C19 C 1.3596(3) 0.2071(5) 0.10882(16) 0.0492(7) Uani 1 1 d . . .
H19A H 1.4068 0.3019 0.1368 0.074 Uiso 1 1 calc R . .
H19B H 1.4133 0.1665 0.0715 0.074 Uiso 1 1 calc R . .
H19C H 1.3429 0.1058 0.1399 0.074 Uiso 1 1 calc R . .
C20 C 0.8578(3) 0.4992(5) 0.36980(17) 0.0515(7) Uani 1 1 d . . .
H20 H 0.8103 0.5891 0.3374 0.062 Uiso 1 1 calc R B .
C21 C 0.8559(5) 0.5794(7) 0.4456(2) 0.0834(13) Uani 1 1 d . . .
H21A H 0.9082 0.5031 0.4798 0.125 Uiso 1 1 calc R . .
H21B H 0.7646 0.5851 0.4582 0.125 Uiso 1 1 calc R . .
H21C H 0.8936 0.7007 0.4466 0.125 Uiso 1 1 calc R . .
C22 C 0.7733(3) 0.3258(5) 0.36117(17) 0.0506(7) Uani 1 1 d . . .
H22 H 0.7851 0.2715 0.3138 0.061 Uiso 1 1 calc R . .
C23 C 0.7961(3) 0.1788(6) 0.4183(2) 0.0621(9) Uani 1 1 d . . .
H23A H 0.7973 0.2341 0.4660 0.075 Uiso 0.50 1 calc PR A 1
H23B H 0.8830 0.1214 0.4145 0.075 Uiso 0.50 1 calc PR A 1
H23C H 0.8436 0.2318 0.4604 0.075 Uiso 0.50 1 d PR A 2
H23D H 0.8506 0.0838 0.3994 0.075 Uiso 0.50 1 d PR A 2
O4 O 0.4204(6) 0.3111(16) 0.3261(5) 0.109(3) Uani 0.50 1 d PU B 1
C24 C 0.6844(9) 0.0318(18) 0.4096(7) 0.088(3) Uani 0.50 1 d PDU B 1
H24A H 0.7059 -0.0503 0.3711 0.106 Uiso 0.50 1 calc PR B 1
H24B H 0.6899 -0.0397 0.4540 0.106 Uiso 0.50 1 calc PR B 1
C25 C 0.5460(11) 0.088(2) 0.3941(8) 0.095(3) Uani 0.50 1 d PDU B 1
H25 H 0.5315 0.0084 0.3514 0.114 Uiso 0.50 1 calc PR B 1
C26 C 0.5294(15) 0.256(2) 0.3517(8) 0.092(3) Uani 0.50 1 d PDU B 1
C27 C 0.4356(17) 0.009(3) 0.4286(10) 0.137(5) Uani 0.45 1 d PDU B 1
H27A H 0.4342 0.0592 0.4764 0.205 Uiso 0.45 1 calc PR B 1
H27B H 0.4469 -0.1217 0.4319 0.205 Uiso 0.45 1 calc PR B 1
H27C H 0.3522 0.0365 0.4006 0.205 Uiso 0.45 1 calc PR B 1
O4' O 0.4266(6) 0.3871(11) 0.3742(5) 0.098(2) Uani 0.50 1 d PU B 2
C24' C 0.6715(8) 0.0936(14) 0.4401(5) 0.071(2) Uani 0.50 1 d PDU B 2
H24C H 0.6414 0.1570 0.4817 0.086 Uiso 0.50 1 calc PR B 2
H24D H 0.6876 -0.0339 0.4530 0.086 Uiso 0.50 1 calc PR B 2
C25' C 0.5619(9) 0.1085(15) 0.3737(6) 0.0674(19) Uani 0.50 1 d PDU B 2
H25' H 0.5975 0.0667 0.3289 0.081 Uiso 0.50 1 calc PR B 2
C26' C 0.5321(12) 0.3140(15) 0.3710(7) 0.069(2) Uani 0.50 1 d PDU B 2
C27' C 0.4313(9) 0.0041(16) 0.3875(6) 0.088(3) Uani 0.55 1 d PDU B 2
H27D H 0.3677 0.0132 0.3455 0.132 Uiso 0.55 1 calc PR B 2
H27E H 0.3931 0.0571 0.4284 0.132 Uiso 0.55 1 calc PR B 2
H27F H 0.4521 -0.1225 0.3972 0.132 Uiso 0.55 1 calc PR B 2
C28 C 1.3437(3) 0.2927(5) -0.19896(16) 0.0527(8) Uani 1 1 d . . .
C29 C 1.4486(4) 0.2233(7) -0.24422(18) 0.0729(11) Uani 1 1 d . . .
H29A H 1.5292 0.2950 -0.2350 0.109 Uiso 1 1 calc R . .
H29B H 1.4164 0.2327 -0.2945 0.109 Uiso 1 1 calc R . .
H29C H 1.4680 0.0973 -0.2324 0.109 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 C13 1.456(3) . ?
O1 C14 1.457(3) . ?
O2 C16 1.408(4) . ?
O2 H2 0.8200 . ?
O3 C26' 1.238(12) . ?
O3 C22 1.460(4) . ?
O3 C26 1.480(16) . ?
O5 C28 1.186(4) . ?
O6 C28 1.326(4) . ?
O6 C3 1.451(3) . ?
C1 C2 1.520(4) . ?
C1 C10 1.538(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.508(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.502(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.535(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.518(4) . ?
C5 C10 1.541(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.512(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.523(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.499(4) . ?
C8 C9 1.530(4) . ?
C8 H8 0.9800 . ?
C9 C11 1.535(4) . ?
C9 C10 1.553(4) . ?
C9 H9 0.9800 . ?
C10 C19 1.531(4) . ?
C11 C12 1.538(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.500(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.459(4) . ?
C13 C17 1.534(4) . ?
C14 C15 1.500(4) . ?
C15 C16 1.530(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.581(4) . ?
C16 H16 0.9800 . ?
C17 C18 1.526(4) . ?
C17 C20 1.550(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C22 1.519(5) . ?
C20 C21 1.523(5) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.509(5) . ?
C22 H22 0.9800 . ?
C23 C24' 1.477(9) . ?
C23 C24 1.543(12) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9555 . ?
C23 H23D 0.9656 . ?
O4 C26 1.212(16) . ?
C24 C25 1.441(13) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C27 1.442(14) . ?
C25 C26 1.460(15) . ?
C25 H25 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O4' C26' 1.185(12) . ?
C24' C25' 1.572(13) . ?
C24' H24C 0.9700 . ?
C24' H24D 0.9700 . ?
C25' C26' 1.527(13) . ?
C25' C27' 1.549(10) . ?
C25' H25' 0.9800 . ?
C27' H27D 0.9600 . ?
C27' H27E 0.9600 . ?
C27' H27F 0.9600 . ?
C28 C29 1.488(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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
C13 O1 C14 60.12(15) . . ?
C16 O2 H2 109.5 . . ?
C26' O3 C22 128.1(6) . . ?
C26' O3 C26 21.1(8) . . ?
C22 O3 C26 114.4(7) . . ?
C28 O6 C3 118.2(3) . . ?
C2 C1 C10 113.7(2) . . ?
C2 C1 H1A 108.8 . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C10 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.6(3) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
O6 C3 C4 109.3(2) . . ?
O6 C3 C2 106.4(2) . . ?
C4 C3 C2 112.0(2) . . ?
O6 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C3 C4 C5 111.6(2) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 112.0(2) . . ?
C6 C5 C10 113.6(2) . . ?
C4 C5 C10 112.7(2) . . ?
C6 C5 H5 105.9 . . ?
C4 C5 H5 105.9 . . ?
C10 C5 H5 105.9 . . ?
C7 C6 C5 110.9(2) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 111.1(2) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C14 C8 C7 111.5(2) . . ?
C14 C8 C9 112.3(2) . . ?
C7 C8 C9 111.6(2) . . ?
C14 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
C8 C9 C11 109.2(2) . . ?
C8 C9 C10 110.8(2) . . ?
C11 C9 C10 116.2(2) . . ?
C8 C9 H9 106.7 . . ?
C11 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
C19 C10 C1 109.5(2) . . ?
C19 C10 C5 112.3(2) . . ?
C1 C10 C5 106.4(2) . . ?
C19 C10 C9 110.7(2) . . ?
C1 C10 C9 110.5(2) . . ?
C5 C10 C9 107.3(2) . . ?
C9 C11 C12 111.9(2) . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.6(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 O1 59.99(16) . . ?
C14 C13 C12 119.5(2) . . ?
O1 C13 C12 114.6(2) . . ?
C14 C13 C17 108.8(2) . . ?
O1 C13 C17 112.0(2) . . ?
C12 C13 C17 124.7(2) . . ?
C13 C14 O1 59.90(16) . . ?
C13 C14 C8 123.8(2) . . ?
O1 C14 C8 115.6(2) . . ?
C13 C14 C15 109.6(2) . . ?
O1 C14 C15 111.9(2) . . ?
C8 C14 C15 120.8(2) . . ?
C14 C15 C16 104.1(2) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
O2 C16 C15 111.1(3) . . ?
O2 C16 C17 115.1(2) . . ?
C15 C16 C17 104.4(2) . . ?
O2 C16 H16 108.7 . . ?
C15 C16 H16 108.7 . . ?
C17 C16 H16 108.7 . . ?
C18 C17 C13 107.5(2) . . ?
C18 C17 C20 113.7(2) . . ?
C13 C17 C20 115.7(2) . . ?
C18 C17 C16 108.3(2) . . ?
C13 C17 C16 101.8(2) . . ?
C20 C17 C16 108.9(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C21 111.3(3) . . ?
C22 C20 C17 117.1(3) . . ?
C21 C20 C17 111.9(3) . . ?
C22 C20 H20 105.1 . . ?
C21 C20 H20 105.1 . . ?
C17 C20 H20 105.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 C23 110.2(2) . . ?
O3 C22 C20 102.1(3) . . ?
C23 C22 C20 118.1(3) . . ?
O3 C22 H22 108.7 . . ?
C23 C22 H22 108.7 . . ?
C20 C22 H22 108.7 . . ?
C24' C23 C22 114.5(4) . . ?
C24' C23 C24 28.4(5) . . ?
C22 C23 C24 111.1(5) . . ?
C24' C23 H23A 82.3 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C24' C23 H23B 128.1 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C24' C23 H23C 108.2 . . ?
C22 C23 H23C 108.5 . . ?
C24 C23 H23C 131.6 . . ?
H23A C23 H23C 29.0 . . ?
H23B C23 H23C 81.7 . . ?
C24' C23 H23D 108.2 . . ?
C22 C23 H23D 107.9 . . ?
C24 C23 H23D 83.5 . . ?
H23A C23 H23D 131.9 . . ?
H23B C23 H23D 29.4 . . ?
H23C C23 H23D 109.5 . . ?
C25 C24 C23 119.5(10) . . ?
C25 C24 H24A 107.5 . . ?
C23 C24 H24A 107.5 . . ?
C25 C24 H24B 107.5 . . ?
C23 C24 H24B 107.5 . . ?
H24A C24 H24B 107.0 . . ?
C27 C25 C24 123.6(12) . . ?
C27 C25 C26 121.4(13) . . ?
C24 C25 C26 113.9(11) . . ?
C27 C25 H25 93.5 . . ?
C24 C25 H25 93.5 . . ?
C26 C25 H25 93.5 . . ?
O4 C26 C25 122.7(13) . . ?
O4 C26 O3 114.9(12) . . ?
C25 C26 O3 119.1(12) . . ?
C23 C24' C25' 107.3(6) . . ?
C23 C24' H24C 110.3 . . ?
C25' C24' H24C 110.3 . . ?
C23 C24' H24D 110.3 . . ?
C25' C24' H24D 110.3 . . ?
H24C C24' H24D 108.5 . . ?
C26' C25' C27' 108.9(9) . . ?
C26' C25' C24' 102.2(9) . . ?
C27' C25' C24' 111.7(8) . . ?
C26' C25' H25' 111.2 . . ?
C27' C25' H25' 111.2 . . ?
C24' C25' H25' 111.2 . . ?
O4' C26' O3 123.2(10) . . ?
O4' C26' C25' 127.6(10) . . ?
O3 C26' C25' 109.0(8) . . ?
C25' C27' H27D 109.5 . . ?
C25' C27' H27E 109.5 . . ?
H27D C27' H27E 109.5 . . ?
C25' C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?
O5 C28 O6 124.7(3) . . ?
O5 C28 C29 124.6(3) . . ?
O6 C28 C29 110.7(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C10 C1 C2 C3 -55.9(3) . . . . ?
C28 O6 C3 C4 -82.1(3) . . . . ?
C28 O6 C3 C2 156.8(3) . . . . ?
C1 C2 C3 O6 171.7(2) . . . . ?
C1 C2 C3 C4 52.4(3) . . . . ?
O6 C3 C4 C5 -170.5(2) . . . . ?
C2 C3 C4 C5 -52.9(3) . . . . ?
C3 C4 C5 C6 -173.8(2) . . . . ?
C3 C4 C5 C10 56.6(3) . . . . ?
C4 C5 C6 C7 174.6(2) . . . . ?
C10 C5 C6 C7 -56.3(3) . . . . ?
C5 C6 C7 C8 53.8(3) . . . . ?
C6 C7 C8 C14 177.6(2) . . . . ?
C6 C7 C8 C9 -55.9(3) . . . . ?
C14 C8 C9 C11 -46.5(3) . . . . ?
C7 C8 C9 C11 -172.5(2) . . . . ?
C14 C8 C9 C10 -175.7(2) . . . . ?
C7 C8 C9 C10 58.3(3) . . . . ?
C2 C1 C10 C19 -65.4(3) . . . . ?
C2 C1 C10 C5 56.3(3) . . . . ?
C2 C1 C10 C9 172.4(2) . . . . ?
C6 C5 C10 C19 -65.1(3) . . . . ?
C4 C5 C10 C19 63.6(3) . . . . ?
C6 C5 C10 C1 175.0(2) . . . . ?
C4 C5 C10 C1 -56.2(3) . . . . ?
C6 C5 C10 C9 56.8(3) . . . . ?
C4 C5 C10 C9 -174.5(2) . . . . ?
C8 C9 C10 C19 66.1(3) . . . . ?
C11 C9 C10 C19 -59.3(3) . . . . ?
C8 C9 C10 C1 -172.4(2) . . . . ?
C11 C9 C10 C1 62.2(3) . . . . ?
C8 C9 C10 C5 -56.8(3) . . . . ?
C11 C9 C10 C5 177.8(2) . . . . ?
C8 C9 C11 C12 64.7(3) . . . . ?
C10 C9 C11 C12 -169.0(2) . . . . ?
C9 C11 C12 C13 -48.0(3) . . . . ?
C14 O1 C13 C12 -111.2(2) . . . . ?
C14 O1 C13 C17 99.7(2) . . . . ?
C11 C12 C13 C14 15.2(4) . . . . ?
C11 C12 C13 O1 83.3(3) . . . . ?
C11 C12 C13 C17 -132.0(3) . . . . ?
C12 C13 C14 O1 103.0(3) . . . . ?
C17 C13 C14 O1 -105.1(2) . . . . ?
O1 C13 C14 C8 -102.3(3) . . . . ?
C12 C13 C14 C8 0.7(4) . . . . ?
C17 C13 C14 C8 152.7(2) . . . . ?
O1 C13 C14 C15 104.5(2) . . . . ?
C12 C13 C14 C15 -152.5(3) . . . . ?
C17 C13 C14 C15 -0.5(3) . . . . ?
C13 O1 C14 C8 115.8(3) . . . . ?
C13 O1 C14 C15 -100.7(2) . . . . ?
C7 C8 C14 C13 141.7(3) . . . . ?
C9 C8 C14 C13 15.6(3) . . . . ?
C7 C8 C14 O1 72.1(3) . . . . ?
C9 C8 C14 O1 -54.0(3) . . . . ?
C7 C8 C14 C15 -67.9(3) . . . . ?
C9 C8 C14 C15 166.0(2) . . . . ?
C13 C14 C15 C16 -20.2(3) . . . . ?
O1 C14 C15 C16 44.3(3) . . . . ?
C8 C14 C15 C16 -174.3(2) . . . . ?
C14 C15 C16 O2 -92.3(3) . . . . ?
C14 C15 C16 C17 32.3(3) . . . . ?
C14 C13 C17 C18 -93.6(3) . . . . ?
O1 C13 C17 C18 -158.0(2) . . . . ?
C12 C13 C17 C18 56.6(3) . . . . ?
C14 C13 C17 C20 138.0(3) . . . . ?
O1 C13 C17 C20 73.7(3) . . . . ?
C12 C13 C17 C20 -71.8(4) . . . . ?
C14 C13 C17 C16 20.2(3) . . . . ?
O1 C13 C17 C16 -44.2(3) . . . . ?
C12 C13 C17 C16 170.3(2) . . . . ?
O2 C16 C17 C18 -156.9(3) . . . . ?
C15 C16 C17 C18 81.1(3) . . . . ?
O2 C16 C17 C13 89.9(3) . . . . ?
C15 C16 C17 C13 -32.0(3) . . . . ?
O2 C16 C17 C20 -32.8(3) . . . . ?
C15 C16 C17 C20 -154.7(2) . . . . ?
C18 C17 C20 C22 -65.5(4) . . . . ?
C13 C17 C20 C22 59.7(4) . . . . ?
C16 C17 C20 C22 173.6(3) . . . . ?
C18 C17 C20 C21 64.7(4) . . . . ?
C13 C17 C20 C21 -170.1(3) . . . . ?
C16 C17 C20 C21 -56.2(4) . . . . ?
C26' O3 C22 C23 -34.9(9) . . . . ?
C26 O3 C22 C23 -53.8(7) . . . . ?
C26' O3 C22 C20 -161.2(8) . . . . ?
C26 O3 C22 C20 179.9(7) . . . . ?
C21 C20 C22 O3 71.4(4) . . . . ?
C17 C20 C22 O3 -158.2(3) . . . . ?
C21 C20 C22 C23 -49.7(4) . . . . ?
C17 C20 C22 C23 80.8(3) . . . . ?
O3 C22 C23 C24' 21.3(6) . . . . ?
C20 C22 C23 C24' 138.1(5) . . . . ?
O3 C22 C23 C24 51.9(6) . . . . ?
C20 C22 C23 C24 168.7(5) . . . . ?
C24' C23 C24 C25 60.1(13) . . . . ?
C22 C23 C24 C25 -42.7(13) . . . . ?
C23 C24 C25 C27 -137.0(15) . . . . ?
C23 C24 C25 C26 31(2) . . . . ?
C27 C25 C26 O4 -21(3) . . . . ?
C24 C25 C26 O4 170.6(14) . . . . ?
C27 C25 C26 O3 137.5(15) . . . . ?
C24 C25 C26 O3 -31(2) . . . . ?
C26' O3 C26 O4 69(3) . . . . ?
C22 O3 C26 O4 -155.7(10) . . . . ?
C26' O3 C26 C25 -91(3) . . . . ?
C22 O3 C26 C25 44.1(17) . . . . ?
C22 C23 C24' C25' 27.5(9) . . . . ?
C24 C23 C24' C25' -61.8(14) . . . . ?
C23 C24' C25' C26' -70.0(9) . . . . ?
C23 C24' C25' C27' 173.7(8) . . . . ?
C22 O3 C26' O4' 174.2(9) . . . . ?
C26 O3 C26' O4' -131(4) . . . . ?
C22 O3 C26' C25' -10.0(14) . . . . ?
C26 O3 C26' C25' 45(2) . . . . ?
C27' C25' C26' O4' -4(2) . . . . ?
C24' C25' C26' O4' -122.7(13) . . . . ?
C27' C25' C26' O3 -180.0(8) . . . . ?
C24' C25' C26' O3 61.7(12) . . . . ?
C3 O6 C28 O5 -5.4(5) . . . . ?
C3 O6 C28 C29 174.8(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
O2 H2 O5 0.82 2.51 3.217(4) 145.2 2_755
O2 H2 O1 0.82 2.25 2.798(3) 124.4 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
