# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_an255-abs_a
_database_code_depnum_ccdc_archive 'CCDC 1579205'
_audit_update_record             
;
2017-10-10 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C84 H80 O8'
_chemical_formula_sum            'C84 H80 O8'
_chemical_formula_weight         1217.48

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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   13.0450(4)
_cell_length_b                   13.0450(4)
_cell_length_c                   40.2669(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6852.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    198(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      65.04

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             2592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.208
_exptl_absorpt_coefficient_mu    0.586
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2665
_exptl_absorpt_correction_T_max  0.4774
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      198(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17469
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         3.561
_diffrn_reflns_theta_max         68.257
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3122
_reflns_number_gt                2917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.7 (Macrae, 2015)'
_computing_publication_material  'enCIFer 1.5.1 (Allen et al. 2014)'
_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)+(0.0733P)²+2.9429P] 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_number_reflns         3122
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48667(7) 0.44626(7) 0.40840(2) 0.0408(2) Uani 1 1 d . . . . .
C1 C 0.50065(11) 0.53879(12) 0.42638(3) 0.0487(4) Uani 1 1 d . . . . .
H1A H 0.5722 0.5624 0.4233 0.058 Uiso 1 1 calc R U . . .
H1B H 0.4905 0.5248 0.4503 0.058 Uiso 1 1 calc R U . . .
C2 C 0.43101(11) 0.62083(11) 0.41625(3) 0.0468(3) Uani 1 1 d . . . . .
C3 C 0.37356(12) 0.68703(11) 0.40753(3) 0.0495(4) Uani 1 1 d . . . . .
O4 O 0.26438(12) 0.82145(9) 0.41943(3) 0.0726(4) Uani 1 1 d . . . . .
C4 C 0.29749(12) 0.76301(10) 0.39839(4) 0.0510(4) Uani 1 1 d . . . . .
C5 C 0.26121(12) 0.76446(10) 0.36358(4) 0.0491(4) Uani 1 1 d . . . . .
C6 C 0.31018(15) 0.70960(12) 0.33901(4) 0.0616(4) Uani 1 1 d . . . . .
H6A H 0.3694 0.6704 0.3441 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2730(2) 0.71174(15) 0.30693(5) 0.0829(6) Uani 1 1 d . . . . .
H7A H 0.3070 0.6743 0.2900 0.099 Uiso 1 1 calc R U . . .
C8 C 0.1867(2) 0.76803(15) 0.29941(5) 0.0843(6) Uani 1 1 d . . . . .
H8A H 0.1612 0.7690 0.2773 0.101 Uiso 1 1 calc R U . . .
C9 C 0.13737(17) 0.82278(15) 0.32379(5) 0.0763(5) Uani 1 1 d . . . . .
H9A H 0.0779 0.8616 0.3186 0.092 Uiso 1 1 calc R U . . .
C10 C 0.17429(14) 0.82120(13) 0.35577(5) 0.0633(4) Uani 1 1 d . . . . .
H10A H 0.1402 0.8591 0.3726 0.076 Uiso 1 1 calc R U . . .
C11 C 0.49372(9) 0.45498(9) 0.37388(3) 0.0341(3) Uani 1 1 d . . . . .
C12 C 0.40345(9) 0.45058(9) 0.35547(3) 0.0346(3) Uani 1 1 d . . . . .
C13 C 0.30001(9) 0.43854(9) 0.37217(3) 0.0369(3) Uani 1 1 d . . . . .
H13A H 0.2892 0.4969 0.3875 0.044 Uiso 1 1 calc R U . . .
H13B H 0.2457 0.4414 0.3550 0.044 Uiso 1 1 calc R U . . .
C14 C 0.41046(10) 0.45696(9) 0.32094(3) 0.0371(3) Uani 1 1 d . . . . .
H14A H 0.3494 0.4538 0.3081 0.044 Uiso 1 1 calc R U . . .
C15 C 0.50369(10) 0.46781(9) 0.30468(3) 0.0385(3) Uani 1 1 d . . . . .
C16 C 0.59205(10) 0.46974(9) 0.32417(3) 0.0382(3) Uani 1 1 d . . . . .
H16A H 0.6566 0.4775 0.3135 0.046 Uiso 1 1 calc R U . . .
C17 C 0.58945(9) 0.46083(9) 0.35857(3) 0.0351(3) Uani 1 1 d . . . . .
C18 C 0.51284(12) 0.47436(11) 0.26669(3) 0.0473(3) Uani 1 1 d . . . . .
C19 C 0.55401(17) 0.57930(15) 0.25699(4) 0.0725(5) Uani 1 1 d . . . . .
H19A H 0.6210 0.5901 0.2674 0.109 Uiso 1 1 calc R U . . .
H19B H 0.5062 0.6325 0.2645 0.109 Uiso 1 1 calc R U . . .
H19C H 0.5613 0.5830 0.2328 0.109 Uiso 1 1 calc R U . . .
C20 C 0.40967(14) 0.45862(15) 0.24938(4) 0.0642(5) Uani 1 1 d . . . . .
H20A H 0.3621 0.5129 0.2561 0.096 Uiso 1 1 calc R U . . .
H20B H 0.3814 0.3917 0.2556 0.096 Uiso 1 1 calc R U . . .
H20C H 0.4194 0.4611 0.2253 0.096 Uiso 1 1 calc R U . . .
C21 C 0.58626(16) 0.39065(16) 0.25429(4) 0.0732(5) Uani 1 1 d . . . . .
H21A H 0.6553 0.4040 0.2628 0.110 Uiso 1 1 calc R U . . .
H21B H 0.5876 0.3910 0.2300 0.110 Uiso 1 1 calc R U . . .
H21C H 0.5627 0.3236 0.2622 0.110 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.3975(14) . ?
O1 C1 1.4192(17) . ?
C1 C2 1.462(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.196(2) . ?
C3 C4 1.450(2) . ?
O4 C4 1.2186(18) . ?
C4 C5 1.480(2) . ?
C5 C6 1.378(2) . ?
C5 C10 1.390(2) . ?
C6 C7 1.380(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.374(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.375(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3927(17) . ?
C11 C17 1.3949(17) . ?
C12 C14 1.3958(17) . ?
C12 C13 1.5158(16) . ?
C13 C17 1.5140(16) 16_656 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3886(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3949(18) . ?
C15 C18 1.5368(17) . ?
C16 C17 1.3902(17) . ?
C16 H16A 0.9500 . ?
C17 C13 1.5140(16) 11_666 ?
C18 C19 1.521(2) . ?
C18 C20 1.530(2) . ?
C18 C21 1.536(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C1 115.45(10) . . ?
O1 C1 C2 113.60(11) . . ?
O1 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
O1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 178.95(15) . . ?
C2 C3 C4 175.43(16) . . ?
O4 C4 C3 119.58(15) . . ?
O4 C4 C5 122.49(15) . . ?
C3 C4 C5 117.91(13) . . ?
C6 C5 C10 119.50(15) . . ?
C6 C5 C4 121.69(15) . . ?
C10 C5 C4 118.80(14) . . ?
C5 C6 C7 119.90(17) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C8 C7 C6 120.25(19) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 120.18(19) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 119.83(19) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C9 C10 C5 120.35(17) . . ?
C9 C10 H10A 119.8 . . ?
C5 C10 H10A 119.8 . . ?
C12 C11 C17 121.59(11) . . ?
C12 C11 O1 118.06(10) . . ?
C17 C11 O1 120.20(10) . . ?
C11 C12 C14 118.19(11) . . ?
C11 C12 C13 121.39(11) . . ?
C14 C12 C13 120.42(10) . . ?
C17 C13 C12 113.50(10) 16_656 . ?
C17 C13 H13A 108.9 16_656 . ?
C12 C13 H13A 108.9 . . ?
C17 C13 H13B 108.9 16_656 . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C12 122.23(11) . . ?
C15 C14 H14A 118.9 . . ?
C12 C14 H14A 118.9 . . ?
C14 C15 C16 117.39(12) . . ?
C14 C15 C18 122.91(12) . . ?
C16 C15 C18 119.67(12) . . ?
C17 C16 C15 122.62(11) . . ?
C17 C16 H16A 118.7 . . ?
C15 C16 H16A 118.7 . . ?
C16 C17 C11 117.83(11) . . ?
C16 C17 C13 119.83(11) . 11_666 ?
C11 C17 C13 122.19(11) . 11_666 ?
C19 C18 C20 108.33(14) . . ?
C19 C18 C21 109.65(15) . . ?
C20 C18 C21 107.76(14) . . ?
C19 C18 C15 109.44(12) . . ?
C20 C18 C15 112.20(12) . . ?
C21 C18 C15 109.42(12) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C11 O1 C1 C2 55.54(15) . . . . ?
O4 C4 C5 C6 169.62(16) . . . . ?
C3 C4 C5 C6 -11.9(2) . . . . ?
O4 C4 C5 C10 -11.7(2) . . . . ?
C3 C4 C5 C10 166.85(14) . . . . ?
C10 C5 C6 C7 0.3(3) . . . . ?
C4 C5 C6 C7 179.00(17) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C4 C5 C10 C9 -178.83(16) . . . . ?
C1 O1 C11 C12 -105.52(12) . . . . ?
C1 O1 C11 C17 78.75(14) . . . . ?
C17 C11 C12 C14 -2.93(17) . . . . ?
O1 C11 C12 C14 -178.59(10) . . . . ?
C17 C11 C12 C13 176.70(11) . . . . ?
O1 C11 C12 C13 1.04(16) . . . . ?
C11 C12 C13 C17 -62.10(15) . . . 16_656 ?
C14 C12 C13 C17 117.52(12) . . . 16_656 ?
C11 C12 C14 C15 -0.24(17) . . . . ?
C13 C12 C14 C15 -179.87(11) . . . . ?
C12 C14 C15 C16 1.51(18) . . . . ?
C12 C14 C15 C18 179.66(11) . . . . ?
C14 C15 C16 C17 0.31(18) . . . . ?
C18 C15 C16 C17 -177.90(11) . . . . ?
C15 C16 C17 C11 -3.30(18) . . . . ?
C15 C16 C17 C13 172.25(11) . . . 11_666 ?
C12 C11 C17 C16 4.62(17) . . . . ?
O1 C11 C17 C16 -179.80(10) . . . . ?
C12 C11 C17 C13 -170.82(11) . . . 11_666 ?
O1 C11 C17 C13 4.76(17) . . . 11_666 ?
C14 C15 C18 C19 115.52(16) . . . . ?
C16 C15 C18 C19 -66.37(17) . . . . ?
C14 C15 C18 C20 -4.76(19) . . . . ?
C16 C15 C18 C20 173.34(13) . . . . ?
C14 C15 C18 C21 -124.31(15) . . . . ?
C16 C15 C18 C21 53.79(17) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.076

