# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc20lmw4
_database_code_depnum_ccdc_archive 'CCDC 1864956'
_audit_update_record             
;
2018-08-31 deposited with the CCDC.
2018-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        bf-54
_chemical_name_common            'Baefrutone A'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H48 O7'
_chemical_formula_weight         580.73

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                   11.27460(10)
_cell_length_b                   16.1738(2)
_cell_length_c                   18.2342(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3325.06(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    8307
_cell_measurement_theta_min      4.5880
_cell_measurement_theta_max      71.2300

_exptl_crystal_description       block
_exptl_crystal_colour            'yellowish crystals'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.638
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_T_min  0.82734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            12053
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.653
_diffrn_reflns_theta_max         71.403
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6255
_reflns_number_gt                5869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.990

_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, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_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)+(0.0645P)²+0.2277P] 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
_refine_ls_extinction_coef       0.0029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2421 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.10(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6255
_refine_ls_number_parameters     394
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O6 O 0.62512(15) 0.63508(9) 0.68637(8) 0.0606(4) Uani 1 1 d . . . . .
O1 O 0.77136(15) 0.55676(10) 0.42646(9) 0.0641(4) Uani 1 1 d . . . . .
O4 O 0.84228(16) 0.46159(12) 0.52825(9) 0.0697(5) Uani 1 1 d . . . . .
H19 H 0.8148 0.4923 0.4968 0.105 Uiso 1 1 calc R U . . .
O5 O 0.96665(16) 0.50050(14) 0.77641(10) 0.0783(5) Uani 1 1 d . . . . .
H18 H 1.0133 0.4636 0.7655 0.117 Uiso 1 1 calc R U . . .
O2 O 0.6251(3) 0.80598(11) 0.33148(11) 0.0961(7) Uani 1 1 d . . . . .
O7 O 1.07586(19) 0.40505(15) 0.69482(12) 0.0939(6) Uani 1 1 d . . . . .
O3 O 0.5180(3) 0.71854(16) 0.57141(11) 0.1172(10) Uani 1 1 d . . . . .
H36 H 0.5448 0.6918 0.6059 0.176 Uiso 1 1 calc DR U . . .
C5' C 0.7990(2) 0.56831(14) 0.73321(11) 0.0562(5) Uani 1 1 d . . . . .
C6' C 0.71988(19) 0.58328(12) 0.67695(11) 0.0503(4) Uani 1 1 d . . . . .
C1 C 0.70344(18) 0.61704(12) 0.43436(12) 0.0520(4) Uani 1 1 d . . . . .
C1' C 0.72689(18) 0.54494(12) 0.60779(11) 0.0490(4) Uani 1 1 d . . . . .
C4' C 0.8922(2) 0.51454(15) 0.71948(12) 0.0588(5) Uani 1 1 d . . . . .
C6 C 0.63336(19) 0.62620(13) 0.50003(11) 0.0536(5) Uani 1 1 d . . . . .
C2' C 0.82585(18) 0.49539(13) 0.59483(12) 0.0527(5) Uani 1 1 d . . . . .
C2 C 0.6988(2) 0.67750(13) 0.37476(13) 0.0589(5) Uani 1 1 d . . . . .
C7 C 0.62338(19) 0.55491(13) 0.55451(11) 0.0519(4) Uani 1 1 d . . . . .
H7 H 0.5572 0.5713 0.5862 0.062 Uiso 1 1 calc DR U . . .
C3' C 0.91032(19) 0.47667(14) 0.65066(13) 0.0572(5) Uani 1 1 d . . . . .
C3 C 0.6327(3) 0.74511(14) 0.38405(14) 0.0701(6) Uani 1 1 d . . . . .
C7' C 1.0114(2) 0.42051(17) 0.64132(15) 0.0693(6) Uani 1 1 d . . . . .
C11' C 0.7838(2) 0.60601(18) 0.80832(13) 0.0699(6) Uani 1 1 d . . . . .
H2BA H 0.8394 0.6513 0.8141 0.084 Uiso 1 1 calc R U . . .
H2BB H 0.8017 0.5648 0.8454 0.084 Uiso 1 1 calc R U . . .
C8 C 0.5784(2) 0.47375(15) 0.51769(13) 0.0626(5) Uani 1 1 d . . . . .
H8 H 0.6384 0.4550 0.4825 0.075 Uiso 1 1 calc R U . . .
C6'' C 0.4773(3) 0.68185(17) 0.76401(14) 0.0792(8) Uani 1 1 d . . . . .
H20 H 0.4266 0.6929 0.7214 0.095 Uiso 1 1 calc R U . . .
C2'' C 0.6587(3) 0.63773(16) 0.81975(12) 0.0686(6) Uani 1 1 d . . . . .
H3BA H 0.6603 0.6759 0.8615 0.082 Uiso 1 1 calc R U . . .
C4'' C 0.4468(3) 0.60980(19) 0.81253(14) 0.0763(7) Uani 1 1 d . . . . .
C5 C 0.5768(3) 0.69869(17) 0.50970(13) 0.0749(7) Uani 1 1 d . . . . .
C3'' C 0.5645(2) 0.57223(17) 0.83561(14) 0.0681(6) Uani 1 1 d . . . . .
H24A H 0.5804 0.5223 0.8079 0.082 Uiso 1 1 calc R U . . .
H24B H 0.5635 0.5586 0.8874 0.082 Uiso 1 1 calc R U . . .
C1'' C 0.6087(3) 0.68492(14) 0.75390(13) 0.0711(7) Uani 1 1 d . . . . .
C4 C 0.5675(4) 0.76648(17) 0.45280(16) 0.0933(11) Uani 1 1 d . . . . .
C5'' C 0.4264(4) 0.6960(2) 0.83965(17) 0.1017(12) Uani 1 1 d . . . . .
H23A H 0.4792 0.7171 0.8773 0.122 Uiso 1 1 calc R U . . .
H23B H 0.3451 0.7153 0.8431 0.122 Uiso 1 1 calc R U . . .
C10 C 0.5602(3) 0.40634(18) 0.57431(18) 0.0875(9) Uani 1 1 d . . . . .
H10A H 0.6340 0.3949 0.5985 0.131 Uiso 1 1 calc R U . . .
H10B H 0.5321 0.3571 0.5505 0.131 Uiso 1 1 calc R U . . .
H10C H 0.5027 0.4243 0.6098 0.131 Uiso 1 1 calc R U . . .
C8'' C 0.3416(3) 0.5546(3) 0.7967(2) 0.0991(10) Uani 1 1 d . . . . .
H22 H 0.2735 0.5908 0.7874 0.119 Uiso 1 1 calc R U . . .
C11 C 0.7717(3) 0.65911(19) 0.30830(17) 0.0815(8) Uani 1 1 d . . . . .
H11A H 0.8507 0.6443 0.3230 0.122 Uiso 1 1 calc R U . . .
H11B H 0.7747 0.7072 0.2774 0.122 Uiso 1 1 calc R U . . .
H11C H 0.7367 0.6141 0.2818 0.122 Uiso 1 1 calc R U . . .
C9 C 0.4632(3) 0.4898(2) 0.47652(19) 0.0921(9) Uani 1 1 d . . . . .
H9A H 0.4056 0.5128 0.5095 0.138 Uiso 1 1 calc R U . . .
H9B H 0.4336 0.4388 0.4568 0.138 Uiso 1 1 calc R U . . .
H9C H 0.4776 0.5280 0.4372 0.138 Uiso 1 1 calc R U . . .
C8' C 1.0408(3) 0.3756(2) 0.57081(18) 0.0930(10) Uani 1 1 d . . . . .
H17 H 1.0230 0.4124 0.5296 0.112 Uiso 1 1 calc R U . . .
C33 C 0.5670(4) 0.7856(3) 0.26543(19) 0.1022(11) Uani 1 1 d . . . . .
H33A H 0.5613 0.8339 0.2351 0.153 Uiso 1 1 calc R U . . .
H33B H 0.4888 0.7653 0.2761 0.153 Uiso 1 1 calc R U . . .
H33C H 0.6113 0.7436 0.2402 0.153 Uiso 1 1 calc R U . . .
C7'' C 0.6641(5) 0.76838(19) 0.7404(2) 0.1207(16) Uani 1 1 d . . . . .
H25A H 0.7474 0.7617 0.7314 0.181 Uiso 1 1 calc R U . . .
H25B H 0.6527 0.8029 0.7826 0.181 Uiso 1 1 calc R U . . .
H25C H 0.6274 0.7937 0.6985 0.181 Uiso 1 1 calc R U . . .
C12 C 0.4333(5) 0.7768(3) 0.4355(2) 0.147(2) Uani 1 1 d . . . . .
H12A H 0.4229 0.8200 0.4000 0.220 Uiso 1 1 calc R U . . .
H12B H 0.3915 0.7909 0.4796 0.220 Uiso 1 1 calc R U . . .
H12C H 0.4025 0.7259 0.4162 0.220 Uiso 1 1 calc R U . . .
C9' C 0.9615(6) 0.2999(3) 0.5650(2) 0.141(2) Uani 1 1 d . . . . .
H3AA H 0.9827 0.2609 0.6024 0.212 Uiso 1 1 calc R U . . .
H3AB H 0.9715 0.2749 0.5176 0.212 Uiso 1 1 calc R U . . .
H3AC H 0.8802 0.3161 0.5712 0.212 Uiso 1 1 calc R U . . .
10'' C 0.3603(4) 0.5038(3) 0.7287(3) 0.1187(14) Uani 1 1 d . . . . .
H7AA H 0.3739 0.5398 0.6877 0.178 Uiso 1 1 calc R U . . .
H7AB H 0.2912 0.4706 0.7196 0.178 Uiso 1 1 calc R U . . .
H7AC H 0.4279 0.4684 0.7353 0.178 Uiso 1 1 calc R U . . .
C9'' C 0.3098(4) 0.5006(4) 0.8617(3) 0.149(2) Uani 1 1 d . . . . .
H8AA H 0.3773 0.4679 0.8754 0.224 Uiso 1 1 calc R U . . .
H8AB H 0.2451 0.4649 0.8487 0.224 Uiso 1 1 calc R U . . .
H8AC H 0.2868 0.5349 0.9023 0.224 Uiso 1 1 calc R U . . .
C13 C 0.6188(8) 0.8474(2) 0.4842(3) 0.183(3) Uani 1 1 d . . . . .
H13A H 0.7010 0.8395 0.4961 0.274 Uiso 1 1 calc R U . . .
H13B H 0.5759 0.8625 0.5277 0.274 Uiso 1 1 calc R U . . .
H13C H 0.6115 0.8906 0.4484 0.274 Uiso 1 1 calc R U . . .
C10' C 1.1713(5) 0.3524(6) 0.5672(3) 0.199(4) Uani 1 1 d . . . . .
H4AA H 1.2187 0.4017 0.5671 0.299 Uiso 1 1 calc R U . . .
H4AB H 1.1861 0.3215 0.5232 0.299 Uiso 1 1 calc R U . . .
H4AC H 1.1915 0.3192 0.6091 0.299 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
O6 C6' 1.368(3) . ?
O6 C1'' 1.483(3) . ?
O1 C1 1.248(3) . ?
O4 C2' 1.344(3) . ?
O4 H19 0.8200 . ?
O5 C4' 1.354(3) . ?
O5 H18 0.8200 . ?
O2 C3 1.377(3) . ?
O2 C33 1.410(4) . ?
O7 C7' 1.242(3) . ?
O3 C5 1.345(3) . ?
O3 H36 0.8200 . ?
C5' C6' 1.381(3) . ?
C5' C4' 1.387(3) . ?
C5' C11' 1.509(3) . ?
C6' C1' 1.408(3) . ?
C1 C6 1.442(3) . ?
C1 C2 1.463(3) . ?
C1' C2' 1.394(3) . ?
C1' C7 1.527(3) . ?
C4' C3' 1.411(3) . ?
C6 C5 1.346(3) . ?
C6 C7 1.526(3) . ?
C2' C3' 1.427(3) . ?
C2 C3 1.334(3) . ?
C2 C11 1.494(4) . ?
C7 C8 1.559(3) . ?
C7 H7 0.9800 . ?
C3' C7' 1.467(3) . ?
C3 C4 1.494(4) . ?
C7' C8' 1.514(4) . ?
C11' C2'' 1.515(4) . ?
C11' H2BA 0.9700 . ?
C11' H2BB 0.9700 . ?
C8 C10 1.516(4) . ?
C8 C9 1.523(4) . ?
C8 H8 0.9800 . ?
C6'' C1'' 1.495(5) . ?
C6'' C4'' 1.503(4) . ?
C6'' C5'' 1.511(4) . ?
C6'' H20 0.9800 . ?
C2'' C3'' 1.528(4) . ?
C2'' C1'' 1.530(3) . ?
C2'' H3BA 0.9800 . ?
C4'' C5'' 1.497(4) . ?
C4'' C8'' 1.513(5) . ?
C4'' C3'' 1.519(4) . ?
C5 C4 1.513(4) . ?
C3'' H24A 0.9700 . ?
C3'' H24B 0.9700 . ?
C1'' C7'' 1.507(4) . ?
C4 C13 1.541(6) . ?
C4 C12 1.555(6) . ?
C5'' H23A 0.9700 . ?
C5'' H23B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8'' 10'' 1.503(6) . ?
C8'' C9'' 1.515(6) . ?
C8'' H22 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8' C9' 1.519(7) . ?
C8' C10' 1.520(5) . ?
C8' H17 0.9800 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C7'' H25A 0.9600 . ?
C7'' H25B 0.9600 . ?
C7'' H25C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C9' H3AA 0.9600 . ?
C9' H3AB 0.9600 . ?
C9' H3AC 0.9600 . ?
10'' H7AA 0.9600 . ?
10'' H7AB 0.9600 . ?
10'' H7AC 0.9600 . ?
C9'' H8AA 0.9600 . ?
C9'' H8AB 0.9600 . ?
C9'' H8AC 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10' H4AA 0.9600 . ?
C10' H4AB 0.9600 . ?
C10' H4AC 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
C6' O6 C1'' 122.29(18) . . ?
C2' O4 H19 109.5 . . ?
C4' O5 H18 109.5 . . ?
C3 O2 C33 117.1(2) . . ?
C5 O3 H36 109.5 . . ?
C6' C5' C4' 117.7(2) . . ?
C6' C5' C11' 122.0(2) . . ?
C4' C5' C11' 120.2(2) . . ?
O6 C6' C5' 121.23(19) . . ?
O6 C6' C1' 115.22(17) . . ?
C5' C6' C1' 123.51(19) . . ?
O1 C1 C6 120.81(19) . . ?
O1 C1 C2 117.3(2) . . ?
C6 C1 C2 121.91(19) . . ?
C2' C1' C6' 116.76(18) . . ?
C2' C1' C7 124.37(18) . . ?
C6' C1' C7 118.73(18) . . ?
O5 C4' C5' 115.9(2) . . ?
O5 C4' C3' 121.3(2) . . ?
C5' C4' C3' 122.82(19) . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 C7 122.5(2) . . ?
C1 C6 C7 120.21(17) . . ?
O4 C2' C1' 119.82(18) . . ?
O4 C2' C3' 117.78(19) . . ?
C1' C2' C3' 122.4(2) . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 C11 125.0(2) . . ?
C1 C2 C11 116.7(2) . . ?
C6 C7 C1' 115.95(17) . . ?
C6 C7 C8 112.33(17) . . ?
C1' C7 C8 115.69(17) . . ?
C6 C7 H7 103.6 . . ?
C1' C7 H7 103.6 . . ?
C8 C7 H7 103.6 . . ?
C4' C3' C2' 116.5(2) . . ?
C4' C3' C7' 119.0(2) . . ?
C2' C3' C7' 124.5(2) . . ?
C2 C3 O2 122.2(3) . . ?
C2 C3 C4 124.8(2) . . ?
O2 C3 C4 112.9(2) . . ?
O7 C7' C3' 119.2(3) . . ?
O7 C7' C8' 116.2(2) . . ?
C3' C7' C8' 124.5(2) . . ?
C5' C11' C2'' 111.56(19) . . ?
C5' C11' H2BA 109.3 . . ?
C2'' C11' H2BA 109.3 . . ?
C5' C11' H2BB 109.3 . . ?
C2'' C11' H2BB 109.3 . . ?
H2BA C11' H2BB 108.0 . . ?
C10 C8 C9 110.0(2) . . ?
C10 C8 C7 110.9(2) . . ?
C9 C8 C7 110.2(2) . . ?
C10 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C1'' C6'' C4'' 109.0(2) . . ?
C1'' C6'' C5'' 118.9(3) . . ?
C4'' C6'' C5'' 59.6(2) . . ?
C1'' C6'' H20 118.3 . . ?
C4'' C6'' H20 118.3 . . ?
C5'' C6'' H20 118.3 . . ?
C11' C2'' C3'' 116.0(2) . . ?
C11' C2'' C1'' 113.8(2) . . ?
C3'' C2'' C1'' 103.8(2) . . ?
C11' C2'' H3BA 107.6 . . ?
C3'' C2'' H3BA 107.6 . . ?
C1'' C2'' H3BA 107.6 . . ?
C5'' C4'' C6'' 60.5(2) . . ?
C5'' C4'' C8'' 119.5(3) . . ?
C6'' C4'' C8'' 121.6(3) . . ?
C5'' C4'' C3'' 114.6(3) . . ?
C6'' C4'' C3'' 105.9(2) . . ?
C8'' C4'' C3'' 120.1(3) . . ?
O3 C5 C6 123.4(2) . . ?
O3 C5 C4 111.5(2) . . ?
C6 C5 C4 125.0(2) . . ?
C4'' C3'' C2'' 106.1(2) . . ?
C4'' C3'' H24A 110.5 . . ?
C2'' C3'' H24A 110.5 . . ?
C4'' C3'' H24B 110.5 . . ?
C2'' C3'' H24B 110.5 . . ?
H24A C3'' H24B 108.7 . . ?
O6 C1'' C6'' 102.0(2) . . ?
O6 C1'' C7'' 107.4(2) . . ?
C6'' C1'' C7'' 117.4(3) . . ?
O6 C1'' C2'' 109.53(18) . . ?
C6'' C1'' C2'' 104.6(2) . . ?
C7'' C1'' C2'' 115.0(3) . . ?
C3 C4 C5 111.9(2) . . ?
C3 C4 C13 108.9(4) . . ?
C5 C4 C13 109.6(3) . . ?
C3 C4 C12 109.5(3) . . ?
C5 C4 C12 106.5(3) . . ?
C13 C4 C12 110.4(4) . . ?
C4'' C5'' C6'' 59.93(19) . . ?
C4'' C5'' H23A 117.8 . . ?
C6'' C5'' H23A 117.8 . . ?
C4'' C5'' H23B 117.8 . . ?
C6'' C5'' H23B 117.8 . . ?
H23A C5'' H23B 114.9 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
10'' C8'' C4'' 111.7(3) . . ?
10'' C8'' C9'' 111.4(4) . . ?
C4'' C8'' C9'' 112.1(3) . . ?
10'' C8'' H22 107.1 . . ?
C4'' C8'' H22 107.1 . . ?
C9'' C8'' H22 107.1 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7' C8' C9' 108.5(3) . . ?
C7' C8' C10' 111.6(4) . . ?
C9' C8' C10' 111.5(5) . . ?
C7' C8' H17 108.4 . . ?
C9' C8' H17 108.4 . . ?
C10' C8' H17 108.4 . . ?
O2 C33 H33A 109.5 . . ?
O2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C1'' C7'' H25A 109.5 . . ?
C1'' C7'' H25B 109.5 . . ?
H25A C7'' H25B 109.5 . . ?
C1'' C7'' H25C 109.5 . . ?
H25A C7'' H25C 109.5 . . ?
H25B C7'' H25C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8' C9' H3AA 109.5 . . ?
C8' C9' H3AB 109.5 . . ?
H3AA C9' H3AB 109.5 . . ?
C8' C9' H3AC 109.5 . . ?
H3AA C9' H3AC 109.5 . . ?
H3AB C9' H3AC 109.5 . . ?
C8'' 10'' H7AA 109.5 . . ?
C8'' 10'' H7AB 109.5 . . ?
H7AA 10'' H7AB 109.5 . . ?
C8'' 10'' H7AC 109.5 . . ?
H7AA 10'' H7AC 109.5 . . ?
H7AB 10'' H7AC 109.5 . . ?
C8'' C9'' H8AA 109.5 . . ?
C8'' C9'' H8AB 109.5 . . ?
H8AA C9'' H8AB 109.5 . . ?
C8'' C9'' H8AC 109.5 . . ?
H8AA C9'' H8AC 109.5 . . ?
H8AB C9'' H8AC 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8' C10' H4AA 109.5 . . ?
C8' C10' H4AB 109.5 . . ?
H4AA C10' H4AB 109.5 . . ?
C8' C10' H4AC 109.5 . . ?
H4AA C10' H4AC 109.5 . . ?
H4AB C10' H4AC 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
C1'' O6 C6' C5' 6.8(3) . . . . ?
C1'' O6 C6' C1' -175.66(19) . . . . ?
C4' C5' C6' O6 179.52(19) . . . . ?
C11' C5' C6' O6 1.7(3) . . . . ?
C4' C5' C6' C1' 2.2(3) . . . . ?
C11' C5' C6' C1' -175.6(2) . . . . ?
O6 C6' C1' C2' 176.51(18) . . . . ?
C5' C6' C1' C2' -6.0(3) . . . . ?
O6 C6' C1' C7 -7.7(3) . . . . ?
C5' C6' C1' C7 169.76(19) . . . . ?
C6' C5' C4' O5 -179.0(2) . . . . ?
C11' C5' C4' O5 -1.1(3) . . . . ?
C6' C5' C4' C3' 1.4(3) . . . . ?
C11' C5' C4' C3' 179.3(2) . . . . ?
O1 C1 C6 C5 169.8(2) . . . . ?
C2 C1 C6 C5 -9.8(3) . . . . ?
O1 C1 C6 C7 -11.4(3) . . . . ?
C2 C1 C6 C7 168.97(19) . . . . ?
C6' C1' C2' O4 -175.39(19) . . . . ?
C7 C1' C2' O4 9.1(3) . . . . ?
C6' C1' C2' C3' 6.5(3) . . . . ?
C7 C1' C2' C3' -169.0(2) . . . . ?
O1 C1 C2 C3 -175.7(2) . . . . ?
C6 C1 C2 C3 3.9(3) . . . . ?
O1 C1 C2 C11 2.9(3) . . . . ?
C6 C1 C2 C11 -177.5(2) . . . . ?
C5 C6 C7 C1' -100.3(3) . . . . ?
C1 C6 C7 C1' 81.0(2) . . . . ?
C5 C6 C7 C8 123.6(2) . . . . ?
C1 C6 C7 C8 -55.1(3) . . . . ?
C2' C1' C7 C6 -91.4(2) . . . . ?
C6' C1' C7 C6 93.2(2) . . . . ?
C2' C1' C7 C8 43.3(3) . . . . ?
C6' C1' C7 C8 -132.1(2) . . . . ?
O5 C4' C3' C2' 179.5(2) . . . . ?
C5' C4' C3' C2' -0.9(3) . . . . ?
O5 C4' C3' C7' 0.5(3) . . . . ?
C5' C4' C3' C7' -179.9(2) . . . . ?
O4 C2' C3' C4' 178.6(2) . . . . ?
C1' C2' C3' C4' -3.2(3) . . . . ?
O4 C2' C3' C7' -2.5(3) . . . . ?
C1' C2' C3' C7' 175.7(2) . . . . ?
C1 C2 C3 O2 178.7(2) . . . . ?
C11 C2 C3 O2 0.2(4) . . . . ?
C1 C2 C3 C4 3.6(4) . . . . ?
C11 C2 C3 C4 -174.9(3) . . . . ?
C33 O2 C3 C2 67.9(4) . . . . ?
C33 O2 C3 C4 -116.4(3) . . . . ?
C4' C3' C7' O7 2.8(4) . . . . ?
C2' C3' C7' O7 -176.1(2) . . . . ?
C4' C3' C7' C8' 179.7(3) . . . . ?
C2' C3' C7' C8' 0.8(4) . . . . ?
C6' C5' C11' C2'' 17.2(3) . . . . ?
C4' C5' C11' C2'' -160.5(2) . . . . ?
C6 C7 C8 C10 -175.4(2) . . . . ?
C1' C7 C8 C10 48.3(3) . . . . ?
C6 C7 C8 C9 -53.3(3) . . . . ?
C1' C7 C8 C9 170.4(2) . . . . ?
C5' C11' C2'' C3'' 76.8(3) . . . . ?
C5' C11' C2'' C1'' -43.5(3) . . . . ?
C1'' C6'' C4'' C5'' 113.1(3) . . . . ?
C1'' C6'' C4'' C8'' -138.6(3) . . . . ?
C5'' C6'' C4'' C8'' 108.4(3) . . . . ?
C1'' C6'' C4'' C3'' 3.5(3) . . . . ?
C5'' C6'' C4'' C3'' -109.6(3) . . . . ?
C1 C6 C5 O3 -173.4(3) . . . . ?
C7 C6 C5 O3 7.9(4) . . . . ?
C1 C6 C5 C4 8.7(4) . . . . ?
C7 C6 C5 C4 -170.1(3) . . . . ?
C5'' C4'' C3'' C2'' -47.4(3) . . . . ?
C6'' C4'' C3'' C2'' 16.9(3) . . . . ?
C8'' C4'' C3'' C2'' 159.7(2) . . . . ?
C11' C2'' C3'' C4'' -156.0(2) . . . . ?
C1'' C2'' C3'' C4'' -30.4(3) . . . . ?
C6' O6 C1'' C6'' -142.8(2) . . . . ?
C6' O6 C1'' C7'' 93.2(3) . . . . ?
C6' O6 C1'' C2'' -32.4(3) . . . . ?
C4'' C6'' C1'' O6 91.7(2) . . . . ?
C5'' C6'' C1'' O6 156.8(2) . . . . ?
C4'' C6'' C1'' C7'' -151.2(3) . . . . ?
C5'' C6'' C1'' C7'' -86.2(3) . . . . ?
C4'' C6'' C1'' C2'' -22.4(3) . . . . ?
C5'' C6'' C1'' C2'' 42.7(3) . . . . ?
C11' C2'' C1'' O6 50.4(3) . . . . ?
C3'' C2'' C1'' O6 -76.6(3) . . . . ?
C11' C2'' C1'' C6'' 159.1(2) . . . . ?
C3'' C2'' C1'' C6'' 32.1(2) . . . . ?
C11' C2'' C1'' C7'' -70.6(3) . . . . ?
C3'' C2'' C1'' C7'' 162.4(3) . . . . ?
C2 C3 C4 C5 -4.6(5) . . . . ?
O2 C3 C4 C5 179.9(3) . . . . ?
C2 C3 C4 C13 116.7(3) . . . . ?
O2 C3 C4 C13 -58.8(4) . . . . ?
C2 C3 C4 C12 -122.5(3) . . . . ?
O2 C3 C4 C12 62.0(4) . . . . ?
O3 C5 C4 C3 179.9(3) . . . . ?
C6 C5 C4 C3 -1.9(5) . . . . ?
O3 C5 C4 C13 59.0(5) . . . . ?
C6 C5 C4 C13 -122.9(5) . . . . ?
O3 C5 C4 C12 -60.5(4) . . . . ?
C6 C5 C4 C12 117.7(4) . . . . ?
C8'' C4'' C5'' C6'' -111.9(3) . . . . ?
C3'' C4'' C5'' C6'' 95.0(3) . . . . ?
C1'' C6'' C5'' C4'' -96.1(3) . . . . ?
C5'' C4'' C8'' 10'' 140.2(3) . . . . ?
C6'' C4'' C8'' 10'' 68.6(4) . . . . ?
C3'' C4'' C8'' 10'' -68.2(4) . . . . ?
C5'' C4'' C8'' C9'' -94.0(4) . . . . ?
C6'' C4'' C8'' C9'' -165.6(3) . . . . ?
C3'' C4'' C8'' C9'' 57.6(4) . . . . ?
O7 C7' C8' C9' 96.5(4) . . . . ?
C3' C7' C8' C9' -80.5(4) . . . . ?
O7 C7' C8' C10' -26.7(5) . . . . ?
C3' C7' C8' C10' 156.3(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
O4 H19 O1 0.82 1.72 2.540(2) 174.1 .
O5 H18 O7 0.82 1.75 2.472(3) 146.3 .
O3 H36 O6 0.82 1.95 2.770(3) 173.6 .

_refine_diff_density_max         0.125
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4

