# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelxl
_audit_block_doi                 10.5517/cc1j03pb
_database_code_depnum_ccdc_archive 'CCDC 1400291'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'compound 1'
_chemical_name_common            LM-56
_chemical_melting_point          ?
_chemical_formula_moiety         C27H34O10
_chemical_formula_sum            'C28 H38 O11'
_chemical_formula_weight         550.58

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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.03740(10)
_cell_length_b                   12.63980(10)
_cell_length_c                   21.0812(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2674.59(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    18373
_cell_measurement_theta_min      3.4820
_cell_measurement_theta_max      69.7190

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.880
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            22499
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.194
_diffrn_reflns_theta_max         69.671
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4923
_reflns_number_gt                4891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.994

_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 (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_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)+(0.0746P)²+0.4413P] 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 x determined using 2092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4923
_refine_ls_number_parameters     377
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
O3 O 0.27692(15) 0.19710(12) 0.18323(7) 0.0291(3) Uani 1 1 d . . . . .
O5 O 0.35444(16) 0.20188(14) 0.01283(7) 0.0349(4) Uani 1 1 d . . . . .
H5 H 0.2763 0.2136 0.0040 0.052 Uiso 1 1 calc R U . . .
O4 O 0.08740(16) 0.24942(15) 0.04394(8) 0.0388(4) Uani 1 1 d . . . . .
H4 H 0.0064 0.2524 0.0394 0.058 Uiso 1 1 calc R U . . .
O2 O 0.10902(18) 0.12609(13) 0.24463(8) 0.0379(4) Uani 1 1 d . . . . .
H2 H 0.1705 0.1010 0.2653 0.057 Uiso 1 1 calc R U . . .
O9 O 0.2445(2) 0.69173(15) 0.25869(11) 0.0543(5) Uani 1 1 d . . . . .
O7 O 0.5673(2) 0.01306(17) 0.03953(10) 0.0531(5) Uani 1 1 d . . . . .
C8 C 0.2637(2) 0.22448(17) 0.11737(10) 0.0280(4) Uani 1 1 d . . . . .
O6 O 0.7252(2) 0.1158(2) 0.07519(14) 0.0701(7) Uani 1 1 d . . . . .
O1 O -0.04976(19) 0.41391(18) 0.13667(11) 0.0532(5) Uani 1 1 d . . . . .
O11 O 0.3291(3) 0.0245(2) 0.30159(12) 0.0642(6) Uani 1 1 d D . . . .
C9 C 0.1177(2) 0.19706(18) 0.10220(10) 0.0308(5) Uani 1 1 d . . . . .
C5 C 0.2306(2) 0.40818(18) 0.22495(11) 0.0320(5) Uani 1 1 d . . . . .
H5A H 0.3277 0.3995 0.2255 0.038 Uiso 1 1 calc R U . . .
C30 C 0.2857(2) 0.34463(18) 0.11172(11) 0.0317(5) Uani 1 1 d . . . . .
H30A H 0.2756 0.3649 0.0676 0.038 Uiso 1 1 calc R U . . .
H30B H 0.3765 0.3606 0.1242 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3321(2) 0.03809(19) 0.07377(11) 0.0333(5) Uani 1 1 d . . . . .
C2 C 0.0517(2) 0.24718(19) 0.16133(11) 0.0327(5) Uani 1 1 d . . . . .
H2A H -0.0376 0.2189 0.1694 0.039 Uiso 1 1 calc R U . . .
C11 C 0.0896(2) 0.0791(2) 0.09664(12) 0.0366(5) Uani 1 1 d . . . . .
H11A H -0.0005 0.0689 0.0813 0.044 Uiso 1 1 calc R U . . .
H11B H 0.0957 0.0470 0.1384 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5061(2) 0.1745(2) 0.09755(11) 0.0358(5) Uani 1 1 d . . . . .
H15A H 0.5324 0.2464 0.0873 0.043 Uiso 1 1 calc R U . . .
H15B H 0.5093 0.1675 0.1433 0.043 Uiso 1 1 calc R U . . .
O8 O 0.4173(2) 0.58548(19) 0.24190(14) 0.0651(6) Uani 1 1 d . . . . .
C14 C 0.3629(2) 0.15911(18) 0.07635(10) 0.0295(4) Uani 1 1 d . . . . .
C7 C 0.3001(3) 0.5974(2) 0.25163(12) 0.0399(5) Uani 1 1 d . . . . .
C1 C 0.0506(2) 0.3649(2) 0.14891(11) 0.0349(5) Uani 1 1 d . . . . .
C10 C 0.1888(2) 0.41303(19) 0.15272(11) 0.0329(5) Uani 1 1 d . . . . .
C29 C 0.0363(3) 0.3347(2) 0.29352(13) 0.0459(6) Uani 1 1 d . . . . .
H29A H -0.0216 0.3687 0.2635 0.069 Uiso 1 1 calc R U . . .
H29B H 0.0495 0.3802 0.3294 0.069 Uiso 1 1 calc R U . . .
H29C H -0.0034 0.2695 0.3073 0.069 Uiso 1 1 calc R U . . .
C12 C 0.1867(3) 0.0233(2) 0.05183(12) 0.0396(5) Uani 1 1 d . . . . .
H12A H 0.1764 0.0517 0.0094 0.048 Uiso 1 1 calc R U . . .
H12B H 0.1658 -0.0516 0.0504 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1518(2) 0.21934(18) 0.21480(10) 0.0301(4) Uani 1 1 d . . . . .
C6 C 0.2011(3) 0.5105(2) 0.26164(13) 0.0392(5) Uani 1 1 d . . . . .
H6A H 0.1138 0.5360 0.2492 0.047 Uiso 1 1 calc R U . . .
H6B H 0.1977 0.4941 0.3066 0.047 Uiso 1 1 calc R U . . .
C18 C 0.3542(3) -0.0184(2) 0.13729(11) 0.0419(6) Uani 1 1 d . . . . .
H18A H 0.3040 0.0168 0.1698 0.063 Uiso 1 1 calc R U . . .
H18B H 0.4471 -0.0167 0.1479 0.063 Uiso 1 1 calc R U . . .
H18C H 0.3251 -0.0905 0.1339 0.063 Uiso 1 1 calc R U . . .
C17 C 0.4280(3) -0.0082(2) 0.02353(12) 0.0421(6) Uani 1 1 d . . . . .
H17 H 0.4086 0.0258 -0.0172 0.051 Uiso 1 1 calc R U . A 1
C16 C 0.6074(3) 0.1005(2) 0.06955(13) 0.0454(6) Uani 1 1 d . . . . .
C28 C 0.2721(3) 0.2797(2) 0.31361(12) 0.0447(6) Uani 1 1 d . . . . .
H28A H 0.2343 0.2248 0.3394 0.067 Uiso 1 1 calc R U . . .
H28B H 0.2919 0.3401 0.3396 0.067 Uiso 1 1 calc R U . . .
H28C H 0.3526 0.2545 0.2942 0.067 Uiso 1 1 calc R U . . .
C4 C 0.1721(2) 0.31140(18) 0.26177(10) 0.0331(5) Uani 1 1 d . . . . .
C19 C 0.1891(3) 0.5254(2) 0.12518(14) 0.0459(6) Uani 1 1 d . . . . .
H19A H 0.1630 0.5230 0.0814 0.069 Uiso 1 1 calc R U . . .
H19B H 0.2770 0.5548 0.1285 0.069 Uiso 1 1 calc R U . . .
H19C H 0.1276 0.5687 0.1484 0.069 Uiso 1 1 calc R U . . .
C25 C 0.3566(4) 0.0065(3) 0.36534(17) 0.0662(9) Uani 1 1 d D . . . .
H25A H 0.3977 0.0682 0.3833 0.099 Uiso 1 1 calc R U . . .
H25B H 0.4160 -0.0527 0.3692 0.099 Uiso 1 1 calc R U . . .
H25C H 0.2752 -0.0085 0.3875 0.099 Uiso 1 1 calc R U . . .
C24 C 0.3298(5) 0.7819(3) 0.2531(2) 0.0775(11) Uani 1 1 d . . . . .
H24A H 0.3962 0.7798 0.2858 0.116 Uiso 1 1 calc R U . . .
H24B H 0.2779 0.8454 0.2573 0.116 Uiso 1 1 calc R U . . .
H24C H 0.3725 0.7812 0.2123 0.116 Uiso 1 1 calc R U . . .
C20 C 0.4216(3) -0.1256(2) 0.01414(13) 0.0486(6) Uani 0.570(4) 1 d . . P B 2
O10 O 0.479(2) -0.2992(16) 0.0233(10) 0.114(4) Uani 0.570(4) 1 d . . P B 2
C23 C 0.3551(9) -0.2918(5) -0.0079(3) 0.0651(14) Uani 0.570(4) 1 d . . P B 2
H23 H 0.3070 -0.3491 -0.0234 0.078 Uiso 0.570(4) 1 calc R U P B 2
C22 C 0.3171(8) -0.1920(5) -0.0119(3) 0.0654(13) Uani 0.570(4) 1 d . . P B 2
H22 H 0.2367 -0.1682 -0.0285 0.079 Uiso 0.570(4) 1 calc R U P B 2
C21 C 0.5138(12) -0.1955(10) 0.0341(6) 0.089(4) Uani 0.570(4) 1 d . . P B 2
H21 H 0.5933 -0.1754 0.0533 0.107 Uiso 0.570(4) 1 calc R U P B 2
C20' C 0.4216(3) -0.1256(2) 0.01414(13) 0.0486(6) Uani 0.430(4) 1 d . . P B 1
C22' C 0.3976(10) -0.1615(6) -0.0443(4) 0.0654(13) Uani 0.430(4) 1 d . . P B 1
H22' H 0.3827 -0.1190 -0.0796 0.079 Uiso 0.430(4) 1 calc R U P B 1
O10' O 0.432(3) -0.297(2) 0.0136(15) 0.114(4) Uani 0.430(4) 1 d . . P B 1
C23' C 0.3981(11) -0.2673(6) -0.0447(4) 0.0651(14) Uani 0.430(4) 1 d . . P B 1
H23' H 0.3787 -0.3113 -0.0788 0.078 Uiso 0.430(4) 1 calc R U P B 1
C21' C 0.4472(15) -0.2120(14) 0.0520(9) 0.089(4) Uani 0.430(4) 1 d . . P B 1
H21' H 0.4700 -0.2121 0.0947 0.107 Uiso 0.430(4) 1 calc R U P B 1
H11 H 0.4007(16) 0.050(4) 0.2862(6) 0.107 Uiso 1 1 d D 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
O3 C8 1.437(2) . ?
O3 C3 1.449(3) . ?
O5 C14 1.446(2) . ?
O5 H5 0.8200 . ?
O4 C9 1.428(3) . ?
O4 H4 0.8200 . ?
O2 C3 1.403(3) . ?
O2 H2 0.8200 . ?
O9 C7 1.325(3) . ?
O9 C24 1.431(4) . ?
O7 C16 1.335(4) . ?
O7 C17 1.464(4) . ?
C8 C30 1.539(3) . ?
C8 C9 1.540(3) . ?
C8 C14 1.556(3) . ?
O6 C16 1.205(4) . ?
O1 C1 1.210(3) . ?
O11 C25 1.391(4) . ?
O11 H11 0.8503(14) . ?
C9 C11 1.522(3) . ?
C9 C2 1.547(3) . ?
C5 C6 1.536(3) . ?
C5 C4 1.563(3) . ?
C5 C10 1.581(3) . ?
C5 H5A 0.9800 . ?
C30 C10 1.562(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C13 C18 1.533(3) . ?
C13 C12 1.543(3) . ?
C13 C17 1.546(3) . ?
C13 C14 1.561(3) . ?
C2 C1 1.511(3) . ?
C2 C3 1.550(3) . ?
C2 H2A 0.9800 . ?
C11 C12 1.529(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 C16 1.502(4) . ?
C15 C14 1.518(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O8 C7 1.204(4) . ?
C7 C6 1.495(4) . ?
C1 C10 1.517(3) . ?
C10 C19 1.535(3) . ?
C29 C4 1.547(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C3 C4 1.541(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 C20 1.498(4) . ?
C17 H17 0.9800 . ?
C28 C4 1.537(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C20 C21 1.347(12) . ?
C20 C22 1.451(7) . ?
O10 C21 1.37(2) . ?
O10 C23 1.413(13) . ?
C23 C22 1.321(9) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C22' C23' 1.338(11) . ?
C22' H22' 0.9300 . ?
O10' C23' 1.33(3) . ?
O10' C21' 1.35(3) . ?
C23' H23' 0.9300 . ?
C21' H21' 0.9300 . ?

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
C8 O3 C3 108.48(15) . . ?
C14 O5 H5 109.5 . . ?
C9 O4 H4 109.5 . . ?
C3 O2 H2 109.5 . . ?
C7 O9 C24 117.1(3) . . ?
C16 O7 C17 123.3(2) . . ?
O3 C8 C30 107.40(18) . . ?
O3 C8 C9 103.56(16) . . ?
C30 C8 C9 110.03(18) . . ?
O3 C8 C14 110.48(17) . . ?
C30 C8 C14 112.90(18) . . ?
C9 C8 C14 111.98(17) . . ?
C25 O11 H11 105.2(4) . . ?
O4 C9 C11 110.40(19) . . ?
O4 C9 C8 106.07(17) . . ?
C11 C9 C8 114.35(18) . . ?
O4 C9 C2 114.34(19) . . ?
C11 C9 C2 112.60(19) . . ?
C8 C9 C2 98.51(17) . . ?
C6 C5 C4 109.66(19) . . ?
C6 C5 C10 113.65(19) . . ?
C4 C5 C10 114.12(18) . . ?
C6 C5 H5A 106.3 . . ?
C4 C5 H5A 106.3 . . ?
C10 C5 H5A 106.3 . . ?
C8 C30 C10 114.46(18) . . ?
C8 C30 H30A 108.6 . . ?
C10 C30 H30A 108.6 . . ?
C8 C30 H30B 108.6 . . ?
C10 C30 H30B 108.6 . . ?
H30A C30 H30B 107.6 . . ?
C18 C13 C12 110.0(2) . . ?
C18 C13 C17 109.4(2) . . ?
C12 C13 C17 109.72(19) . . ?
C18 C13 C14 113.39(19) . . ?
C12 C13 C14 108.45(19) . . ?
C17 C13 C14 105.77(19) . . ?
C1 C2 C9 105.49(18) . . ?
C1 C2 C3 110.8(2) . . ?
C9 C2 C3 102.45(18) . . ?
C1 C2 H2A 112.5 . . ?
C9 C2 H2A 112.5 . . ?
C3 C2 H2A 112.5 . . ?
C9 C11 C12 112.4(2) . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C16 C15 C14 116.4(2) . . ?
C16 C15 H15A 108.2 . . ?
C14 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
C14 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
O5 C14 C15 106.27(17) . . ?
O5 C14 C8 106.16(17) . . ?
C15 C14 C8 111.98(18) . . ?
O5 C14 C13 108.80(17) . . ?
C15 C14 C13 108.86(19) . . ?
C8 C14 C13 114.38(18) . . ?
O8 C7 O9 122.9(3) . . ?
O8 C7 C6 125.6(3) . . ?
O9 C7 C6 111.4(2) . . ?
O1 C1 C2 123.2(2) . . ?
O1 C1 C10 124.6(2) . . ?
C2 C1 C10 112.26(19) . . ?
C1 C10 C19 110.7(2) . . ?
C1 C10 C30 108.56(19) . . ?
C19 C10 C30 107.5(2) . . ?
C1 C10 C5 106.18(19) . . ?
C19 C10 C5 113.6(2) . . ?
C30 C10 C5 110.24(18) . . ?
C4 C29 H29A 109.5 . . ?
C4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C11 C12 C13 111.20(19) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O2 C3 O3 107.94(18) . . ?
O2 C3 C4 112.75(17) . . ?
O3 C3 C4 109.08(18) . . ?
O2 C3 C2 108.57(19) . . ?
O3 C3 C2 105.77(16) . . ?
C4 C3 C2 112.42(19) . . ?
C7 C6 C5 114.8(2) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C17 C20 104.7(2) . . ?
O7 C17 C13 111.5(2) . . ?
C20 C17 C13 116.1(2) . . ?
O7 C17 H17 108.1 . . ?
C13 C17 H17 108.1 . . ?
O6 C16 O7 118.4(3) . . ?
O6 C16 C15 121.7(3) . . ?
O7 C16 C15 119.9(2) . . ?
C4 C28 H28A 109.5 . . ?
C4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C28 C4 C3 110.27(19) . . ?
C28 C4 C29 108.5(2) . . ?
C3 C4 C29 107.8(2) . . ?
C28 C4 C5 108.1(2) . . ?
C3 C4 C5 108.75(17) . . ?
C29 C4 C5 113.4(2) . . ?
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 . . ?
O11 C25 H25A 109.5 . . ?
O11 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O11 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O9 C24 H24A 109.5 . . ?
O9 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O9 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C20 C22 103.6(6) . . ?
C21 C20 C17 125.4(6) . . ?
C22 C20 C17 130.8(3) . . ?
C21 O10 C23 103.6(11) . . ?
C22 C23 O10 110.3(10) . . ?
C22 C23 H23 124.8 . . ?
O10 C23 H23 124.8 . . ?
C23 C22 C20 108.6(6) . . ?
C23 C22 H22 125.7 . . ?
C20 C22 H22 125.7 . . ?
C20 C21 O10 113.7(10) . . ?
C20 C21 H21 123.2 . . ?
O10 C21 H21 123.2 . . ?
C23' C22' H22' 124.9 . . ?
C23' O10' C21' 111(2) . . ?
O10' C23' C22' 105.9(14) . . ?
O10' C23' H23' 127.1 . . ?
C22' C23' H23' 127.1 . . ?
O10' C21' H21' 127.5 . . ?

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
C3 O3 C8 C30 82.0(2) . . . . ?
C3 O3 C8 C9 -34.4(2) . . . . ?
C3 O3 C8 C14 -154.50(17) . . . . ?
O3 C8 C9 O4 163.89(17) . . . . ?
C30 C8 C9 O4 49.3(2) . . . . ?
C14 C8 C9 O4 -77.1(2) . . . . ?
O3 C8 C9 C11 -74.2(2) . . . . ?
C30 C8 C9 C11 171.26(18) . . . . ?
C14 C8 C9 C11 44.8(2) . . . . ?
O3 C8 C9 C2 45.4(2) . . . . ?
C30 C8 C9 C2 -69.1(2) . . . . ?
C14 C8 C9 C2 164.45(18) . . . . ?
O3 C8 C30 C10 -57.4(2) . . . . ?
C9 C8 C30 C10 54.6(2) . . . . ?
C14 C8 C30 C10 -179.47(17) . . . . ?
O4 C9 C2 C1 -35.2(3) . . . . ?
C11 C9 C2 C1 -162.31(19) . . . . ?
C8 C9 C2 C1 76.8(2) . . . . ?
O4 C9 C2 C3 -151.20(18) . . . . ?
C11 C9 C2 C3 81.7(2) . . . . ?
C8 C9 C2 C3 -39.2(2) . . . . ?
O4 C9 C11 C12 68.7(2) . . . . ?
C8 C9 C11 C12 -50.8(3) . . . . ?
C2 C9 C11 C12 -162.2(2) . . . . ?
C16 C15 C14 O5 -75.5(3) . . . . ?
C16 C15 C14 C8 169.0(2) . . . . ?
C16 C15 C14 C13 41.6(3) . . . . ?
O3 C8 C14 O5 -172.65(16) . . . . ?
C30 C8 C14 O5 -52.4(2) . . . . ?
C9 C8 C14 O5 72.5(2) . . . . ?
O3 C8 C14 C15 -57.1(2) . . . . ?
C30 C8 C14 C15 63.2(2) . . . . ?
C9 C8 C14 C15 -171.96(18) . . . . ?
O3 C8 C14 C13 67.4(2) . . . . ?
C30 C8 C14 C13 -172.36(18) . . . . ?
C9 C8 C14 C13 -47.5(2) . . . . ?
C18 C13 C14 O5 173.25(19) . . . . ?
C12 C13 C14 O5 -64.3(2) . . . . ?
C17 C13 C14 O5 53.4(2) . . . . ?
C18 C13 C14 C15 57.8(2) . . . . ?
C12 C13 C14 C15 -179.68(18) . . . . ?
C17 C13 C14 C15 -62.0(2) . . . . ?
C18 C13 C14 C8 -68.2(2) . . . . ?
C12 C13 C14 C8 54.2(2) . . . . ?
C17 C13 C14 C8 171.86(18) . . . . ?
C24 O9 C7 O8 1.2(4) . . . . ?
C24 O9 C7 C6 177.4(3) . . . . ?
C9 C2 C1 O1 107.9(3) . . . . ?
C3 C2 C1 O1 -142.0(2) . . . . ?
C9 C2 C1 C10 -71.3(2) . . . . ?
C3 C2 C1 C10 38.8(3) . . . . ?
O1 C1 C10 C19 -12.3(3) . . . . ?
C2 C1 C10 C19 166.9(2) . . . . ?
O1 C1 C10 C30 -130.1(3) . . . . ?
C2 C1 C10 C30 49.1(2) . . . . ?
O1 C1 C10 C5 111.4(3) . . . . ?
C2 C1 C10 C5 -69.4(2) . . . . ?
C8 C30 C10 C1 -40.7(3) . . . . ?
C8 C30 C10 C19 -160.5(2) . . . . ?
C8 C30 C10 C5 75.2(2) . . . . ?
C6 C5 C10 C1 -95.0(2) . . . . ?
C4 C5 C10 C1 31.8(2) . . . . ?
C6 C5 C10 C19 26.9(3) . . . . ?
C4 C5 C10 C19 153.6(2) . . . . ?
C6 C5 C10 C30 147.6(2) . . . . ?
C4 C5 C10 C30 -85.6(2) . . . . ?
C9 C11 C12 C13 58.1(3) . . . . ?
C18 C13 C12 C11 66.0(3) . . . . ?
C17 C13 C12 C11 -173.6(2) . . . . ?
C14 C13 C12 C11 -58.5(2) . . . . ?
C8 O3 C3 O2 124.37(18) . . . . ?
C8 O3 C3 C4 -112.81(19) . . . . ?
C8 O3 C3 C2 8.3(2) . . . . ?
C1 C2 C3 O2 152.99(19) . . . . ?
C9 C2 C3 O2 -94.9(2) . . . . ?
C1 C2 C3 O3 -91.4(2) . . . . ?
C9 C2 C3 O3 20.7(2) . . . . ?
C1 C2 C3 C4 27.6(3) . . . . ?
C9 C2 C3 C4 139.64(19) . . . . ?
O8 C7 C6 C5 -32.5(4) . . . . ?
O9 C7 C6 C5 151.5(2) . . . . ?
C4 C5 C6 C7 151.8(2) . . . . ?
C10 C5 C6 C7 -79.2(3) . . . . ?
C16 O7 C17 C20 -159.2(3) . . . . ?
C16 O7 C17 C13 -33.0(3) . . . . ?
C18 C13 C17 O7 -64.7(3) . . . . ?
C12 C13 C17 O7 174.6(2) . . . . ?
C14 C13 C17 O7 57.8(2) . . . . ?
C18 C13 C17 C20 55.1(3) . . . . ?
C12 C13 C17 C20 -65.7(3) . . . . ?
C14 C13 C17 C20 177.5(2) . . . . ?
C17 O7 C16 O6 -172.9(3) . . . . ?
C17 O7 C16 C15 9.5(4) . . . . ?
C14 C15 C16 O6 168.2(3) . . . . ?
C14 C15 C16 O7 -14.3(4) . . . . ?
O2 C3 C4 C28 57.0(3) . . . . ?
O3 C3 C4 C28 -62.9(2) . . . . ?
C2 C3 C4 C28 -179.9(2) . . . . ?
O2 C3 C4 C29 -61.3(3) . . . . ?
O3 C3 C4 C29 178.80(18) . . . . ?
C2 C3 C4 C29 61.8(2) . . . . ?
O2 C3 C4 C5 175.37(18) . . . . ?
O3 C3 C4 C5 55.5(2) . . . . ?
C2 C3 C4 C5 -61.5(2) . . . . ?
C6 C5 C4 C28 -82.5(2) . . . . ?
C10 C5 C4 C28 148.7(2) . . . . ?
C6 C5 C4 C3 157.8(2) . . . . ?
C10 C5 C4 C3 29.0(3) . . . . ?
C6 C5 C4 C29 37.9(3) . . . . ?
C10 C5 C4 C29 -90.9(2) . . . . ?
O7 C17 C20 C21 16.9(8) . . . . ?
C13 C17 C20 C21 -106.5(7) . . . . ?
O7 C17 C20 C22 -169.0(5) . . . . ?
C13 C17 C20 C22 67.6(5) . . . . ?
C21 O10 C23 C22 -3(2) . . . . ?
O10 C23 C22 C20 3.4(15) . . . . ?
C21 C20 C22 C23 -2.2(9) . . . . ?
C17 C20 C22 C23 -177.3(5) . . . . ?
C22 C20 C21 O10 0.3(16) . . . . ?
C17 C20 C21 O10 175.7(13) . . . . ?
C23 O10 C21 C20 2(2) . . . . ?
C21' O10' C23' C22' 3(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
O5 H5 O4 0.82 2.12 2.824(2) 143.5 .
O4 H4 O5 0.82 1.97 2.698(2) 148.0 3_455
O2 H2 O11 0.82 2.01 2.823(3) 169.5 .
O11 H11 O8 0.8503(14) 1.973(8) 2.813(3) 169(4) 4_645

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
