# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_yasuda20200115
_database_code_depnum_ccdc_archive 'CCDC 2089131'
loop_
_audit_author_name
_audit_author_address
'Fumitoshi Yagishita'
;Tokushima University
Japan
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C34 H28 I2 O4'
_chemical_formula_moiety         'C34 H28 I2 O4'
_chemical_formula_weight         754.40
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.4916(3)
_cell_length_b                   14.1803(3)
_cell_length_c                   18.3463(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.830(7)
_cell_angle_gamma                90.0000
_cell_volume                     3155.55(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31495
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      68.36
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480.00
_exptl_absorpt_coefficient_mu    15.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.124
_exptl_absorpt_correction_T_max  0.620

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            34209
_diffrn_reflns_av_unetI/netI     0.1029
_diffrn_reflns_av_R_equivalents  0.1702
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         3.888
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5690
_reflns_number_gt                4413
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.2089
_refine_ls_wR_factor_gt          0.1979
_refine_ls_number_restraints     198
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5690
_refine_ls_number_parameters     439
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0978P)²+5.3489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         1.35
_refine_diff_density_min         -1.57
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
I I -0.3257 6.8362
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
I1 I 0.55897(5) 0.68728(4) 0.78330(4) 0.0591(2) Uani 1 1 d . . . . .
I2 I 0.36066(5) 0.49242(4) 0.77906(3) 0.0544(2) Uani 1 1 d . . . . .
O1 O 0.3232(7) 0.0533(4) 0.6317(5) 0.083(2) Uani 1 1 d . . . . .
O2 O 0.7643(6) 0.2511(4) 0.4284(3) 0.0611(17) Uani 1 1 d . . . . .
O3 O 1.0989(5) 0.4617(5) 0.6048(4) 0.0650(18) Uani 1 1 d . . . . .
O4 O 0.5873(10) 0.9903(6) 0.6090(6) 0.056(3) Uani 0.652(18) 1 d . U P A 1
C1 C 0.5427(6) 0.5718(5) 0.7102(5) 0.0426(19) Uani 1 1 d . . . . .
C2 C 0.4807(8) 0.4960(5) 0.7170(5) 0.045(2) Uani 1 1 d . . . . .
C3 C 0.5080(6) 0.4189(5) 0.6713(4) 0.0381(18) Uani 1 1 d . . . . .
C4 C 0.5905(6) 0.4496(5) 0.6412(4) 0.0352(16) Uani 1 1 d . . . . .
C5 C 0.6179(6) 0.5479(5) 0.6641(5) 0.0383(17) Uani 1 1 d . . . . .
C6 C 0.4533(7) 0.3261(5) 0.6584(5) 0.046(2) Uani 1 1 d . . . . .
C7 C 0.4426(8) 0.2694(6) 0.7207(5) 0.053(2) Uani 1 1 d . . . . .
H7 H 0.466562 0.293498 0.770259 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3972(10) 0.1790(6) 0.7095(6) 0.067(3) Uani 1 1 d . . . . .
H8 H 0.389637 0.141818 0.751057 0.081 Uiso 1 1 calc R U . . .
C9 C 0.3639(9) 0.1445(6) 0.6379(7) 0.063(3) Uani 1 1 d . . . . .
C10 C 0.3656(9) 0.2001(6) 0.5748(6) 0.058(3) Uani 1 1 d . . . . .
H10 H 0.336468 0.177412 0.525286 0.070 Uiso 1 1 calc R U . . .
C11 C 0.4119(7) 0.2901(5) 0.5879(5) 0.048(2) Uani 1 1 d . . . . .
H11 H 0.414913 0.328273 0.545871 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2988(12) 0.0106(7) 0.5614(9) 0.099(5) Uani 1 1 d . . . . .
H12A H 0.246135 0.049683 0.525869 0.148 Uiso 1 1 calc R U . . .
H12B H 0.266483 -0.051750 0.564977 0.148 Uiso 1 1 calc R U . . .
H12C H 0.366554 0.003614 0.543841 0.148 Uiso 1 1 calc R U . . .
C13 C 0.6365(6) 0.4008(5) 0.5832(4) 0.0354(17) Uani 1 1 d . . . . .
C14 C 0.6793(8) 0.3079(5) 0.5984(5) 0.047(2) Uani 1 1 d . . . . .
H14 H 0.678075 0.277457 0.644353 0.057 Uiso 1 1 calc R U . . .
C15 C 0.7228(8) 0.2628(6) 0.5449(5) 0.053(2) Uani 1 1 d . . . . .
H15 H 0.754121 0.201863 0.555631 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7218(7) 0.3039(6) 0.4766(5) 0.046(2) Uani 1 1 d . . . . .
C17 C 0.6810(6) 0.3954(6) 0.4624(5) 0.0442(19) Uani 1 1 d . . . . .
H17 H 0.683293 0.426293 0.416902 0.053 Uiso 1 1 calc R U . . .
C18 C 0.6373(6) 0.4402(6) 0.5152(5) 0.0409(18) Uani 1 1 d . . . . .
H18 H 0.606273 0.501226 0.503918 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7607(9) 0.2905(7) 0.3575(5) 0.058(2) Uani 1 1 d . . . . .
H19A H 0.789042 0.244716 0.326716 0.087 Uiso 1 1 calc R U . . .
H19B H 0.806206 0.347591 0.363533 0.087 Uiso 1 1 calc R U . . .
H19C H 0.684388 0.306636 0.332729 0.087 Uiso 1 1 calc R U . . .
C20 C 0.6978(6) 0.6039(5) 0.6469(4) 0.0368(17) Uani 1 1 d . . . . .
C21 C 0.8016(6) 0.5659(5) 0.6350(4) 0.0381(17) Uani 1 1 d . . . . .
C22 C 0.8506(7) 0.4878(5) 0.6765(5) 0.046(2) Uani 1 1 d . . . . .
H22 H 0.815257 0.459210 0.711340 0.056 Uiso 1 1 calc R U . . .
C23 C 0.9494(7) 0.4514(6) 0.6678(5) 0.046(2) Uani 1 1 d . . . . .
H23 H 0.980564 0.397926 0.696289 0.055 Uiso 1 1 calc R U . . .
C24 C 1.0034(7) 0.4920(6) 0.6181(5) 0.050(2) Uani 1 1 d . . . . .
C25 C 0.9559(8) 0.5725(7) 0.5781(5) 0.056(2) Uani 1 1 d . . . . .
H25 H 0.992148 0.601960 0.544173 0.067 Uiso 1 1 calc R U . . .
C26 C 0.8600(7) 0.6087(6) 0.5872(5) 0.048(2) Uani 1 1 d . . . . .
H26 H 0.831260 0.664229 0.560672 0.058 Uiso 1 1 calc R U . . .
C27 C 1.1377(8) 0.3707(7) 0.6339(7) 0.066(3) Uani 1 1 d . . . . .
H27A H 1.081479 0.323059 0.614116 0.099 Uiso 1 1 calc R U . . .
H27B H 1.152594 0.371735 0.688800 0.099 Uiso 1 1 calc R U . . .
H27C H 1.205665 0.355282 0.618596 0.099 Uiso 1 1 calc R U . . .
C28 C 0.6736(15) 0.7063(14) 0.6435(11) 0.030(3) Uani 0.652(18) 1 d . U P A 1
C29 C 0.7527(14) 0.7772(10) 0.6696(10) 0.038(3) Uani 0.652(18) 1 d . U P A 1
H29 H 0.825108 0.759042 0.695224 0.045 Uiso 0.652(18) 1 calc R U P A 1
C30 C 0.7287(15) 0.8721(10) 0.6592(9) 0.042(3) Uani 0.652(18) 1 d . U P A 1
H30 H 0.783640 0.918236 0.677445 0.050 Uiso 0.652(18) 1 calc R U P A 1
C31 C 0.6236(16) 0.8987(11) 0.6220(9) 0.046(3) Uani 0.652(18) 1 d . U P A 1
C32 C 0.5461(14) 0.8311(10) 0.5943(10) 0.047(3) Uani 0.652(18) 1 d . U P A 1
H32 H 0.473927 0.850286 0.568989 0.056 Uiso 0.652(18) 1 calc R U P A 1
C33 C 0.5701(18) 0.7344(12) 0.6021(14) 0.043(3) Uani 0.652(18) 1 d . U P A 1
H33 H 0.516665 0.688830 0.579510 0.051 Uiso 0.652(18) 1 calc R U P A 1
C34 C 0.6672(14) 1.0619(11) 0.6330(9) 0.062(4) Uani 0.652(18) 1 d . U P A 1
H34A H 0.720882 1.060441 0.601882 0.092 Uiso 0.652(18) 1 calc R U P A 1
H34B H 0.705085 1.051046 0.685608 0.092 Uiso 0.652(18) 1 calc R U P A 1
H34C H 0.630731 1.123525 0.628185 0.092 Uiso 0.652(18) 1 calc R U P A 1
O4A O 0.6787(18) 1.0014(13) 0.6407(13) 0.056(5) Uani 0.348(18) 1 d . U P A 2
C28A C 0.697(3) 0.710(3) 0.636(3) 0.044(6) Uani 0.348(18) 1 d . U P A 2
C29A C 0.589(4) 0.753(2) 0.611(3) 0.046(5) Uani 0.348(18) 1 d . U P A 2
H29A H 0.523864 0.717142 0.594860 0.055 Uiso 0.348(18) 1 calc R U P A 2
C30A C 0.677(3) 0.899(2) 0.640(2) 0.050(5) Uani 0.348(18) 1 d . U P A 2
C31A C 0.775(3) 0.857(2) 0.666(2) 0.050(5) Uani 0.348(18) 1 d . U P A 2
H31A H 0.839038 0.894950 0.683575 0.060 Uiso 0.348(18) 1 calc R U P A 2
C32A C 0.588(3) 0.850(2) 0.6118(19) 0.048(5) Uani 0.348(18) 1 d . U P A 2
H32A H 0.520258 0.882037 0.591528 0.058 Uiso 0.348(18) 1 calc R U P A 2
C33A C 0.785(3) 0.760(2) 0.668(2) 0.045(5) Uani 0.348(18) 1 d . U P A 2
H33A H 0.852718 0.730201 0.691814 0.054 Uiso 0.348(18) 1 calc R U P A 2
C34A C 0.571(3) 1.050(2) 0.6231(18) 0.063(7) Uani 0.348(18) 1 d . U P A 2
H34D H 0.538093 1.044986 0.569186 0.094 Uiso 0.348(18) 1 calc R U P A 2
H34E H 0.581968 1.116377 0.637340 0.094 Uiso 0.348(18) 1 calc R U P A 2
H34F H 0.522693 1.020237 0.651174 0.094 Uiso 0.348(18) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
I1 C1 2.095(8) . ?
I2 C2 2.089(9) . ?
O1 C9 1.385(10) . ?
O1 C12 1.391(15) . ?
O2 C16 1.359(9) . ?
O2 C19 1.408(11) . ?
O3 C24 1.343(10) . ?
O3 C27 1.435(11) . ?
O4 C31 1.379(18) . ?
O4 C34 1.417(19) . ?
C1 C2 1.349(11) . ?
C1 C5 1.446(11) . ?
C2 C3 1.466(10) . ?
C3 C4 1.352(10) . ?
C3 C6 1.476(10) . ?
C4 C5 1.473(10) . ?
C4 C13 1.495(10) . ?
C5 C20 1.371(10) . ?
C6 C11 1.371(12) . ?
C6 C7 1.429(12) . ?
C7 C8 1.397(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.370(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(14) . ?
C10 C11 1.399(11) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.369(11) . ?
C13 C14 1.424(10) . ?
C14 C15 1.386(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(11) . ?
C17 C18 1.375(11) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.468(10) . ?
C20 C28 1.48(2) . ?
C20 C28A 1.52(5) . ?
C21 C22 1.399(11) . ?
C21 C26 1.405(11) . ?
C22 C23 1.381(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.408(12) . ?
C25 C26 1.350(12) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C33 1.39(3) . ?
C28 C29 1.41(2) . ?
C29 C30 1.38(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.38(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.37(2) . ?
C32 C33 1.40(2) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
O4A C30A 1.45(3) . ?
O4A C34A 1.47(4) . ?
C28A C33A 1.32(5) . ?
C28A C29A 1.46(5) . ?
C29A C32A 1.37(4) . ?
C29A H29A 0.9500 . ?
C30A C32A 1.32(4) . ?
C30A C31A 1.34(4) . ?
C31A C33A 1.39(4) . ?
C31A H31A 0.9500 . ?
C32A H32A 0.9500 . ?
C33A H33A 0.9500 . ?
C34A H34D 0.9800 . ?
C34A H34E 0.9800 . ?
C34A H34F 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
C9 O1 C12 118.6(9) . . ?
C16 O2 C19 116.8(7) . . ?
C24 O3 C27 117.1(7) . . ?
C31 O4 C34 116.2(13) . . ?
C2 C1 C5 109.6(7) . . ?
C2 C1 I1 122.3(6) . . ?
C5 C1 I1 125.5(5) . . ?
C1 C2 C3 108.9(8) . . ?
C1 C2 I2 124.9(6) . . ?
C3 C2 I2 126.1(6) . . ?
C4 C3 C2 107.3(7) . . ?
C4 C3 C6 126.2(7) . . ?
C2 C3 C6 126.4(7) . . ?
C3 C4 C5 109.6(6) . . ?
C3 C4 C13 127.0(7) . . ?
C5 C4 C13 122.6(6) . . ?
C20 C5 C1 127.6(7) . . ?
C20 C5 C4 127.9(7) . . ?
C1 C5 C4 104.5(6) . . ?
C11 C6 C7 117.3(8) . . ?
C11 C6 C3 122.5(8) . . ?
C7 C6 C3 120.1(8) . . ?
C8 C7 C6 120.7(9) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 119.2(9) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 O1 115.7(9) . . ?
C8 C9 C10 122.0(8) . . ?
O1 C9 C10 122.3(10) . . ?
C11 C10 C9 117.2(9) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C6 C11 C10 123.3(9) . . ?
C6 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.2(7) . . ?
C18 C13 C4 123.2(7) . . ?
C14 C13 C4 118.6(7) . . ?
C15 C14 C13 118.7(8) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C16 C15 C14 121.9(7) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
O2 C16 C15 116.0(7) . . ?
O2 C16 C17 125.0(8) . . ?
C15 C16 C17 119.0(7) . . ?
C18 C17 C16 119.2(8) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C13 C18 C17 122.9(7) . . ?
C13 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 C20 C21 122.7(7) . . ?
C5 C20 C28 115.1(8) . . ?
C21 C20 C28 122.2(8) . . ?
C5 C20 C28A 128.7(15) . . ?
C21 C20 C28A 108.6(15) . . ?
C22 C21 C26 117.2(8) . . ?
C22 C21 C20 119.8(7) . . ?
C26 C21 C20 122.9(7) . . ?
C23 C22 C21 121.3(8) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 120.7(8) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
O3 C24 C23 125.5(8) . . ?
O3 C24 C25 116.6(8) . . ?
C23 C24 C25 118.0(8) . . ?
C26 C25 C24 121.3(8) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C21 121.4(8) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C28 C29 117.7(16) . . ?
C33 C28 C20 117.2(16) . . ?
C29 C28 C20 124.4(15) . . ?
C30 C29 C28 122.4(15) . . ?
C30 C29 H29 118.8 . . ?
C28 C29 H29 118.8 . . ?
C31 C30 C29 119.0(13) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C32 C31 O4 114.9(15) . . ?
C32 C31 C30 119.8(14) . . ?
O4 C31 C30 125.4(16) . . ?
C31 C32 C33 122.0(15) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C28 C33 C32 118.9(15) . . ?
C28 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O4 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C30A O4A C34A 117(2) . . ?
C33A C28A C29A 121(4) . . ?
C33A C28A C20 120(4) . . ?
C29A C28A C20 116(3) . . ?
C32A C29A C28A 116(3) . . ?
C32A C29A H29A 122.1 . . ?
C28A C29A H29A 122.0 . . ?
C32A C30A C31A 121(3) . . ?
C32A C30A O4A 123(3) . . ?
C31A C30A O4A 116(3) . . ?
C30A C31A C33A 121(3) . . ?
C30A C31A H31A 119.3 . . ?
C33A C31A H31A 119.3 . . ?
C30A C32A C29A 122(3) . . ?
C30A C32A H32A 119.2 . . ?
C29A C32A H32A 119.2 . . ?
C28A C33A C31A 118(3) . . ?
C28A C33A H33A 121.2 . . ?
C31A C33A H33A 121.2 . . ?
O4A C34A H34D 109.5 . . ?
O4A C34A H34E 109.5 . . ?
H34D C34A H34E 109.5 . . ?
O4A C34A H34F 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 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
C5 C1 C2 C3 -3.5(10) . . . . ?
I1 C1 C2 C3 -165.7(5) . . . . ?
C5 C1 C2 I2 179.2(6) . . . . ?
I1 C1 C2 I2 16.9(11) . . . . ?
C1 C2 C3 C4 3.3(10) . . . . ?
I2 C2 C3 C4 -179.4(6) . . . . ?
C1 C2 C3 C6 -175.1(8) . . . . ?
I2 C2 C3 C6 2.2(12) . . . . ?
C2 C3 C4 C5 -1.7(9) . . . . ?
C6 C3 C4 C5 176.6(8) . . . . ?
C2 C3 C4 C13 -171.8(7) . . . . ?
C6 C3 C4 C13 6.6(13) . . . . ?
C2 C1 C5 C20 -176.6(8) . . . . ?
I1 C1 C5 C20 -15.0(12) . . . . ?
C2 C1 C5 C4 2.4(9) . . . . ?
I1 C1 C5 C4 163.9(6) . . . . ?
C3 C4 C5 C20 178.7(8) . . . . ?
C13 C4 C5 C20 -10.7(12) . . . . ?
C3 C4 C5 C1 -0.3(9) . . . . ?
C13 C4 C5 C1 170.3(7) . . . . ?
C4 C3 C6 C11 -50.8(12) . . . . ?
C2 C3 C6 C11 127.3(9) . . . . ?
C4 C3 C6 C7 128.7(9) . . . . ?
C2 C3 C6 C7 -53.2(12) . . . . ?
C11 C6 C7 C8 3.5(13) . . . . ?
C3 C6 C7 C8 -176.0(8) . . . . ?
C6 C7 C8 C9 0.6(15) . . . . ?
C7 C8 C9 O1 177.9(9) . . . . ?
C7 C8 C9 C10 -5.2(16) . . . . ?
C12 O1 C9 C8 -173.3(11) . . . . ?
C12 O1 C9 C10 9.8(15) . . . . ?
C8 C9 C10 C11 5.4(15) . . . . ?
O1 C9 C10 C11 -177.9(9) . . . . ?
C7 C6 C11 C10 -3.3(13) . . . . ?
C3 C6 C11 C10 176.2(8) . . . . ?
C9 C10 C11 C6 -1.0(14) . . . . ?
C3 C4 C13 C18 121.1(9) . . . . ?
C5 C4 C13 C18 -47.8(11) . . . . ?
C3 C4 C13 C14 -57.3(11) . . . . ?
C5 C4 C13 C14 133.8(8) . . . . ?
C18 C13 C14 C15 2.0(12) . . . . ?
C4 C13 C14 C15 -179.5(8) . . . . ?
C13 C14 C15 C16 -2.5(14) . . . . ?
C19 O2 C16 C15 177.9(9) . . . . ?
C19 O2 C16 C17 -3.7(13) . . . . ?
C14 C15 C16 O2 -178.2(9) . . . . ?
C14 C15 C16 C17 3.3(14) . . . . ?
O2 C16 C17 C18 178.2(8) . . . . ?
C15 C16 C17 C18 -3.5(13) . . . . ?
C14 C13 C18 C17 -2.4(12) . . . . ?
C4 C13 C18 C17 179.2(7) . . . . ?
C16 C17 C18 C13 3.2(13) . . . . ?
C1 C5 C20 C21 147.7(8) . . . . ?
C4 C5 C20 C21 -31.0(13) . . . . ?
C1 C5 C20 C28 -30.4(14) . . . . ?
C4 C5 C20 C28 150.9(11) . . . . ?
C1 C5 C20 C28A -33(3) . . . . ?
C4 C5 C20 C28A 148(3) . . . . ?
C5 C20 C21 C22 -34.2(11) . . . . ?
C28 C20 C21 C22 143.7(12) . . . . ?
C28A C20 C21 C22 147(2) . . . . ?
C5 C20 C21 C26 150.7(8) . . . . ?
C28 C20 C21 C26 -31.4(15) . . . . ?
C28A C20 C21 C26 -28(2) . . . . ?
C26 C21 C22 C23 -3.3(12) . . . . ?
C20 C21 C22 C23 -178.7(7) . . . . ?
C21 C22 C23 C24 0.6(13) . . . . ?
C27 O3 C24 C23 11.9(13) . . . . ?
C27 O3 C24 C25 -168.8(8) . . . . ?
C22 C23 C24 O3 -179.2(8) . . . . ?
C22 C23 C24 C25 1.5(13) . . . . ?
O3 C24 C25 C26 179.9(9) . . . . ?
C23 C24 C25 C26 -0.8(14) . . . . ?
C24 C25 C26 C21 -2.0(14) . . . . ?
C22 C21 C26 C25 4.0(12) . . . . ?
C20 C21 C26 C25 179.2(8) . . . . ?
C5 C20 C28 C33 -48(2) . . . . ?
C21 C20 C28 C33 133.6(15) . . . . ?
C5 C20 C28 C29 141.5(13) . . . . ?
C21 C20 C28 C29 -37(2) . . . . ?
C33 C28 C29 C30 4(2) . . . . ?
C20 C28 C29 C30 174.0(14) . . . . ?
C28 C29 C30 C31 0(2) . . . . ?
C34 O4 C31 C32 -176.4(14) . . . . ?
C34 O4 C31 C30 3(2) . . . . ?
C29 C30 C31 C32 -2(2) . . . . ?
C29 C30 C31 O4 178.6(14) . . . . ?
O4 C31 C32 C33 179.3(17) . . . . ?
C30 C31 C32 C33 0(3) . . . . ?
C29 C28 C33 C32 -6(3) . . . . ?
C20 C28 C33 C32 -176.7(16) . . . . ?
C31 C32 C33 C28 4(3) . . . . ?
C5 C20 C28A C33A 134(3) . . . . ?
C21 C20 C28A C33A -47(4) . . . . ?
C5 C20 C28A C29A -27(5) . . . . ?
C21 C20 C28A C29A 153(3) . . . . ?
C33A C28A C29A C32A 10(7) . . . . ?
C20 C28A C29A C32A 170(3) . . . . ?
C34A O4A C30A C32A 13(4) . . . . ?
C34A O4A C30A C31A -171(3) . . . . ?
C32A C30A C31A C33A -4(5) . . . . ?
O4A C30A C31A C33A -179(3) . . . . ?
C31A C30A C32A C29A 3(6) . . . . ?
O4A C30A C32A C29A 179(3) . . . . ?
C28A C29A C32A C30A -6(6) . . . . ?
C29A C28A C33A C31A -11(6) . . . . ?
C20 C28A C33A C31A -170(3) . . . . ?
C30A C31A C33A C28A 8(5) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.







#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_hoshi20200819_2
_database_code_depnum_ccdc_archive 'CCDC 2089134'
loop_
_audit_author_name
_audit_author_address
'Fumitoshi Yagishita'
;Tokushima University
Japan
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

#==============================================================================
# start Validation Reply Form
_vrf_THETM01_I                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE:Author Response: Refinement was performed using the reflection data of
1.13 \%A resolution, since the value of mean F^2^/\s(F^2^) in the resolution
shell between 1.08 and 1.13 \%A was less than 2.0. Considerably large Rint
values might be due to a poor quality of the crystal used. This can be
explained partially by the disordered solvent.
;
_vrf_PLAT023_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..       0.44 Ang-1 
RESPONSE:Author Response: Refinement was performed using the reflection data of
1.13 \%A resolution, since the value of mean F^2^/\s(F^2^) in the resolution
shell between 1.08 and 1.13 \%A was less than 2.0. Considerably large Rint
values might be due to a poor quality of the crystal used. This can be
explained partially by the disordered solvent.
;
_vrf_PLAT088_I                   
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.39 Note  
RESPONSE:Author Response: Refinement was performed using the reflection data of
1.13 \%A resolution, since the value of mean F^2^/\s(F^2^) in the resolution
shell between 1.08 and 1.13 \%A was less than 2.0. Considerably large Rint
values might be due to a poor quality of the crystal used. This can be
explained partially by the disordered solvent.
;
# end Validation Reply Form
# CHEMICAL DATA

_chemical_formula_sum            'C48 H42 O6'
_chemical_formula_moiety         'C48 H42 O6'
_chemical_formula_weight         714.86
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   23.5796(15)
_cell_length_b                   15.5436(10)
_cell_length_c                   11.2836(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.796(7)
_cell_angle_gamma                90.0000
_cell_volume                     4032.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13234
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      68.40
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.059
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1512.00
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_T_max  0.964

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13350
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_theta_max         42.976
_diffrn_reflns_theta_min         3.432
_diffrn_reflns_theta_full        42.976
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1456
_reflns_number_gt                1323
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.1266
_refine_ls_wR_factor_ref         0.3326
_refine_ls_wR_factor_gt          0.3261
_refine_ls_number_restraints     413
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1456
_refine_ls_number_parameters     270
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1281P)²+33.5875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.005
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.2716(4) 0.4229(7) 0.4912(9) 0.120(3) Uani 1 1 d D U . . .
O2 O 0.3529(4) 0.9093(5) 0.3697(8) 0.104(3) Uani 1 1 d . U . . .
O3 O 0.2971(4) 0.2019(6) 0.2605(10) 0.128(4) Uani 1 1 d . U . . .
C2 C 0.4581(5) 0.5314(8) 0.2893(10) 0.066(3) Uani 1 1 d . U . . .
C4 C 0.500000 0.3884(11) 0.250000 0.062(4) Uani 1 2 d S TU P . .
C28 C 0.500000 0.4777(11) 0.250000 0.063(4) Uani 1 2 d S TU P . .
C3 C 0.4735(4) 0.6153(8) 0.2788(10) 0.069(3) Uani 1 1 d . U . . .
C17 C 0.4314(5) 0.7055(8) 0.4177(11) 0.075(3) Uani 1 1 d . U . . .
H17 H 0.442086 0.664363 0.478373 0.090 Uiso 1 1 calc R U . . .
C12 C 0.4448(4) 0.6950(7) 0.3024(11) 0.065(3) Uani 1 1 d . U . . .
C6 C 0.4180(5) 0.4512(8) 0.4447(11) 0.079(4) Uani 1 1 d . U . . .
H6 H 0.455335 0.433075 0.481563 0.095 Uiso 1 1 calc R U . . .
C21 C 0.3426(5) 0.3238(8) 0.1800(13) 0.089(4) Uani 1 1 d . U . . .
H21 H 0.307440 0.345977 0.136607 0.107 Uiso 1 1 calc R U . . .
C19 C 0.4468(5) 0.3370(8) 0.2459(11) 0.075(3) Uani 1 1 d . U . . .
C7 C 0.3718(5) 0.4208(8) 0.4889(12) 0.086(4) Uani 1 1 d . U . . .
H7 H 0.377806 0.378824 0.549182 0.103 Uiso 1 1 calc R U . . .
C10 C 0.3548(5) 0.5400(8) 0.3053(12) 0.083(4) Uani 1 1 d . U . . .
H10 H 0.348458 0.581639 0.244602 0.099 Uiso 1 1 calc R U . . .
C24 C 0.4464(5) 0.2642(8) 0.3148(12) 0.083(4) Uani 1 1 d . U . . .
H24 H 0.481281 0.244867 0.362927 0.100 Uiso 1 1 calc R U . . .
C23 C 0.3965(5) 0.2186(8) 0.3153(12) 0.089(4) Uani 1 1 d . U . . .
H23 H 0.397965 0.167995 0.359816 0.107 Uiso 1 1 calc R U . . .
C5 C 0.4112(5) 0.5074(8) 0.3480(10) 0.068(3) Uani 1 1 d . U . . .
C20 C 0.3933(5) 0.3645(8) 0.1768(12) 0.081(4) Uani 1 1 d . U . . .
H20 H 0.392252 0.412229 0.126680 0.098 Uiso 1 1 calc R U . . .
C15 C 0.3832(5) 0.8384(9) 0.3505(13) 0.086(4) Uani 1 1 d . U . . .
C13 C 0.4267(5) 0.7584(8) 0.2151(12) 0.084(4) Uani 1 1 d . U . . .
H13 H 0.435086 0.751506 0.138951 0.101 Uiso 1 1 calc R U . . .
C16 C 0.4013(5) 0.7807(8) 0.4370(12) 0.080(3) Uani 1 1 d . U . . .
H16 H 0.393869 0.790217 0.513520 0.096 Uiso 1 1 calc R U . . .
C14 C 0.3973(5) 0.8300(8) 0.2364(12) 0.086(4) Uani 1 1 d . U . . .
H14 H 0.386843 0.872222 0.177166 0.103 Uiso 1 1 calc R U . . .
C8 C 0.3175(6) 0.4522(10) 0.4445(14) 0.099(4) Uani 1 1 d . U . . .
C9 C 0.3076(6) 0.5109(9) 0.3527(13) 0.102(4) Uani 1 1 d . U . . .
H9 H 0.270247 0.531512 0.321679 0.122 Uiso 1 1 calc R U . . .
C22 C 0.3433(6) 0.2496(9) 0.2476(14) 0.097(4) Uani 1 1 d . U . . .
C25 C 0.2405(6) 0.2380(10) 0.2022(19) 0.166(8) Uani 1 1 d . U . . .
H25A H 0.231047 0.222015 0.117984 0.249 Uiso 1 1 calc R U . . .
H25B H 0.241939 0.299569 0.209029 0.249 Uiso 1 1 calc R U . . .
H25C H 0.211273 0.216117 0.241545 0.249 Uiso 1 1 calc R U . . .
C11 C 0.2637(10) 0.3376(13) 0.524(2) 0.103(8) Uani 0.545(19) 1 d D U P A 1
H11A H 0.291784 0.323558 0.596550 0.155 Uiso 0.545(19) 1 calc R U P A 1
H11B H 0.268770 0.300036 0.459197 0.155 Uiso 0.545(19) 1 calc R U P A 1
H11C H 0.225230 0.330699 0.537258 0.155 Uiso 0.545(19) 1 calc R U P A 1
C26 C 0.3331(11) 0.9158(16) 0.484(2) 0.126(10) Uani 0.59(2) 1 d . U P B 1
H26A H 0.311945 0.864830 0.495497 0.189 Uiso 0.59(2) 1 calc R U P B 1
H26B H 0.308347 0.965139 0.481362 0.189 Uiso 0.59(2) 1 calc R U P B 1
H26C H 0.366223 0.921775 0.550861 0.189 Uiso 0.59(2) 1 calc R U P B 1
C11A C 0.2153(10) 0.457(3) 0.455(3) 0.153(15) Uani 0.455(19) 1 d D U P A 2
H11D H 0.208263 0.496394 0.515884 0.229 Uiso 0.455(19) 1 calc R U P A 2
H11E H 0.187318 0.411413 0.444736 0.229 Uiso 0.455(19) 1 calc R U P A 2
H11F H 0.211783 0.487305 0.379331 0.229 Uiso 0.455(19) 1 calc R U P A 2
C26A C 0.3426(15) 0.980(2) 0.286(3) 0.118(13) Uani 0.41(2) 1 d . U P B 2
H26D H 0.378889 0.998958 0.269677 0.178 Uiso 0.41(2) 1 calc R U P B 2
H26E H 0.325072 1.026658 0.321053 0.178 Uiso 0.41(2) 1 calc R U P B 2
H26F H 0.317052 0.962196 0.211746 0.178 Uiso 0.41(2) 1 calc R U P B 2


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C8 1.382(15) . ?
O1 C11 1.399(17) . ?
O1 C11A 1.406(19) . ?
O2 C15 1.357(14) . ?
O2 C26A 1.44(3) . ?
O2 C26 1.47(2) . ?
O3 C22 1.351(14) . ?
O3 C25 1.464(16) . ?
C2 C3 1.366(14) . ?
C2 C28 1.437(14) . ?
C2 C5 1.458(15) . ?
C4 C28 1.39(2) . ?
C4 C19 1.479(14) . ?
C4 C19 1.479(14) 2_655 ?
C3 C12 1.464(15) . ?
C3 C3 1.53(2) 2_655 ?
C17 C16 1.410(15) . ?
C17 C12 1.414(15) . ?
C17 H17 0.9300 . ?
C12 C13 1.391(15) . ?
C6 C5 1.378(15) . ?
C6 C7 1.379(15) . ?
C6 H6 0.9300 . ?
C21 C20 1.360(15) . ?
C21 C22 1.381(17) . ?
C21 H21 0.9300 . ?
C19 C24 1.375(16) . ?
C19 C20 1.395(15) . ?
C7 C8 1.357(17) . ?
C7 H7 0.9300 . ?
C10 C5 1.405(15) . ?
C10 C9 1.412(15) . ?
C10 H10 0.9300 . ?
C24 C23 1.374(15) . ?
C24 H24 0.9300 . ?
C23 C22 1.402(17) . ?
C23 H23 0.9300 . ?
C20 H20 0.9300 . ?
C15 C16 1.325(16) . ?
C15 C14 1.404(16) . ?
C13 C14 1.361(15) . ?
C13 H13 0.9300 . ?
C16 H16 0.9300 . ?
C14 H14 0.9300 . ?
C8 C9 1.361(17) . ?
C9 H9 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C26A H26D 0.9600 . ?
C26A H26E 0.9600 . ?
C26A H26F 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
C8 O1 C11 124.9(14) . . ?
C8 O1 C11A 122.3(18) . . ?
C15 O2 C26A 122.4(18) . . ?
C15 O2 C26 118.6(14) . . ?
C22 O3 C25 114.7(11) . . ?
C3 C2 C28 108.3(11) . . ?
C3 C2 C5 121.9(10) . . ?
C28 C2 C5 129.3(11) . . ?
C28 C4 C19 122.6(7) . . ?
C28 C4 C19 122.6(7) . 2_655 ?
C19 C4 C19 114.7(15) . 2_655 ?
C4 C28 C2 125.6(7) . . ?
C4 C28 C2 125.6(7) . 2_655 ?
C2 C28 C2 108.9(14) . 2_655 ?
C2 C3 C12 130.4(10) . . ?
C2 C3 C3 107.2(7) . 2_655 ?
C12 C3 C3 122.1(6) . 2_655 ?
C16 C17 C12 117.4(12) . . ?
C16 C17 H17 121.3 . . ?
C12 C17 H17 121.3 . . ?
C13 C12 C17 118.2(11) . . ?
C13 C12 C3 123.5(11) . . ?
C17 C12 C3 118.1(11) . . ?
C5 C6 C7 122.8(12) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C20 C21 C22 120.0(13) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C24 C19 C20 116.7(11) . . ?
C24 C19 C4 122.6(11) . . ?
C20 C19 C4 120.6(12) . . ?
C8 C7 C6 119.9(13) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C10 C9 121.3(12) . . ?
C5 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C23 C24 C19 122.7(12) . . ?
C23 C24 H24 118.7 . . ?
C19 C24 H24 118.7 . . ?
C24 C23 C22 119.0(13) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C6 C5 C10 115.8(11) . . ?
C6 C5 C2 123.7(11) . . ?
C10 C5 C2 120.4(11) . . ?
C21 C20 C19 122.3(13) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C16 C15 O2 121.7(13) . . ?
C16 C15 C14 120.6(13) . . ?
O2 C15 C14 117.6(13) . . ?
C14 C13 C12 122.9(13) . . ?
C14 C13 H13 118.6 . . ?
C12 C13 H13 118.5 . . ?
C15 C16 C17 122.6(13) . . ?
C15 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C13 C14 C15 118.1(13) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C7 C8 C9 120.8(13) . . ?
C7 C8 O1 119.6(14) . . ?
C9 C8 O1 119.6(13) . . ?
C8 C9 C10 119.1(13) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
O3 C22 C21 127.4(13) . . ?
O3 C22 C23 113.4(13) . . ?
C21 C22 C23 119.2(13) . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O1 C11A H11D 109.5 . . ?
O1 C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
O1 C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
O2 C26A H26D 109.5 . . ?
O2 C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
O2 C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 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
C19 C4 C28 C2 23.8(8) . . . . ?
C19 C4 C28 C2 -156.2(8) 2_655 . . . ?
C19 C4 C28 C2 -156.2(8) . . . 2_655 ?
C19 C4 C28 C2 23.8(8) 2_655 . . 2_655 ?
C3 C2 C28 C4 178.4(6) . . . . ?
C5 C2 C28 C4 7.0(13) . . . . ?
C3 C2 C28 C2 -1.6(6) . . . 2_655 ?
C5 C2 C28 C2 -173.0(13) . . . 2_655 ?
C28 C2 C3 C12 177.6(10) . . . . ?
C5 C2 C3 C12 -10.2(19) . . . . ?
C28 C2 C3 C3 3.8(14) . . . 2_655 ?
C5 C2 C3 C3 176.0(11) . . . 2_655 ?
C16 C17 C12 C13 -1.0(15) . . . . ?
C16 C17 C12 C3 -177.1(9) . . . . ?
C2 C3 C12 C13 -121.8(14) . . . . ?
C3 C3 C12 C13 51.2(18) 2_655 . . . ?
C2 C3 C12 C17 54.1(17) . . . . ?
C3 C3 C12 C17 -132.9(13) 2_655 . . . ?
C28 C4 C19 C24 -138.8(9) . . . . ?
C19 C4 C19 C24 41.2(9) 2_655 . . . ?
C28 C4 C19 C20 36.9(12) . . . . ?
C19 C4 C19 C20 -143.1(12) 2_655 . . . ?
C5 C6 C7 C8 -6.1(19) . . . . ?
C20 C19 C24 C23 1.1(18) . . . . ?
C4 C19 C24 C23 176.9(11) . . . . ?
C19 C24 C23 C22 -3.1(19) . . . . ?
C7 C6 C5 C10 7.1(17) . . . . ?
C7 C6 C5 C2 -171.5(11) . . . . ?
C9 C10 C5 C6 -5.1(17) . . . . ?
C9 C10 C5 C2 173.5(11) . . . . ?
C3 C2 C5 C6 -123.9(13) . . . . ?
C28 C2 C5 C6 46.5(16) . . . . ?
C3 C2 C5 C10 57.6(16) . . . . ?
C28 C2 C5 C10 -132.0(12) . . . . ?
C22 C21 C20 C19 -4.1(19) . . . . ?
C24 C19 C20 C21 2.6(18) . . . . ?
C4 C19 C20 C21 -173.4(10) . . . . ?
C26A O2 C15 C16 167.8(19) . . . . ?
C26 O2 C15 C16 -8(2) . . . . ?
C26A O2 C15 C14 -9(2) . . . . ?
C26 O2 C15 C14 174.7(15) . . . . ?
C17 C12 C13 C14 0.6(17) . . . . ?
C3 C12 C13 C14 176.4(11) . . . . ?
O2 C15 C16 C17 178.1(10) . . . . ?
C14 C15 C16 C17 -4.8(19) . . . . ?
C12 C17 C16 C15 3.2(17) . . . . ?
C12 C13 C14 C15 -2.0(18) . . . . ?
C16 C15 C14 C13 4.1(19) . . . . ?
O2 C15 C14 C13 -178.7(11) . . . . ?
C6 C7 C8 C9 3(2) . . . . ?
C6 C7 C8 O1 -178.5(11) . . . . ?
C11 O1 C8 C7 -39(2) . . . . ?
C11A O1 C8 C7 176(2) . . . . ?
C11 O1 C8 C9 139.4(18) . . . . ?
C11A O1 C8 C9 -6(3) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
O1 C8 C9 C10 -179.7(12) . . . . ?
C5 C10 C9 C8 2(2) . . . . ?
C25 O3 C22 C21 -5(2) . . . . ?
C25 O3 C22 C23 173.3(13) . . . . ?
C20 C21 C22 O3 179.9(12) . . . . ?
C20 C21 C22 C23 2(2) . . . . ?
C24 C23 C22 O3 -176.7(11) . . . . ?
C24 C23 C22 C21 2(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.







#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2089168'
loop_
_audit_author_name
_audit_author_address
'Fumitoshi Yagishita'
;Tokushima University
Japan
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         500.56
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.913(4)
_cell_length_b                   7.442(3)
_cell_length_c                   16.072(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.62(3)
_cell_angle_gamma                90
_cell_volume                     1278.5(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    384
_cell_measurement_theta_min      4.1358
_cell_measurement_theta_max      50.3131
_cell_measurement_temperature    173(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528

_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173(2)

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5392
_diffrn_reflns_av_R_equivalents  0.1406
_diffrn_reflns_av_unetI/netI     0.2838
_diffrn_reflns_theta_min         2.807
_diffrn_reflns_theta_max         66.605
_diffrn_reflns_theta_full        66.605
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3532
_reflns_number_gt                1420
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2178
_refine_ls_R_factor_gt           0.1184
_refine_ls_wR_factor_gt          0.2748
_refine_ls_wR_factor_ref         0.3523
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.892
_refine_ls_number_reflns         3532
_refine_ls_number_parameters     299
_refine_ls_number_restraints     493
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.1678P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.509
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 194 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C22 0.4739(5) 0.4856(17) 0.8527(2) 0.046(2) Uani d U . DG 1 . .
C C23 0.5890(6) 0.4029(16) 0.8558(4) 0.046(2) Uani d U . G 1 . .
H H23 0.6072 0.3477 0.8064 0.056 Uiso calc U . R 1 . .
C C24 0.6775(5) 0.4011(17) 0.9313(5) 0.049(2) Uani d U . G 1 . .
H H24 0.7561 0.3446 0.9335 0.059 Uiso calc U . R 1 . .
C C25 0.6509(7) 0.4820(18) 1.0036(3) 0.049(2) Uani d U . G 1 . .
C C26 0.5358(8) 0.5646(17) 1.0004(3) 0.049(2) Uani d U . G 1 . .
H H26 0.5176 0.6199 1.0498 0.059 Uiso calc U . R 1 . .
C C27 0.4473(6) 0.5664(16) 0.9250(4) 0.047(2) Uani d U . G 1 . .
H H27 0.3687 0.6229 0.9228 0.056 Uiso calc U . R 1 . .
C C15 0.2440(3) 0.4992(19) 0.7718(5) 0.048(2) Uani d U . DG 1 . .
C C16 0.1931(6) 0.3960(17) 0.8284(4) 0.049(2) Uani d U . G 1 . .
H H16 0.2459 0.3231 0.8692 0.058 Uiso calc U . R 1 . .
C C17 0.0650(6) 0.3994(17) 0.8255(5) 0.051(2) Uani d U . G 1 . .
H H17 0.0302 0.3288 0.8643 0.061 Uiso calc U . R 1 . .
C C18 -0.0123(3) 0.5060(19) 0.7660(6) 0.050(2) Uani d U . G 1 . .
C C19 0.0386(6) 0.6092(17) 0.7093(5) 0.050(2) Uani d U . G 1 . .
H H19 -0.0142 0.6821 0.6686 0.06 Uiso calc U . R 1 . .
C C20 0.1668(6) 0.6058(17) 0.7122(5) 0.050(2) Uani d U . G 1 . .
H H20 0.2015 0.6764 0.6734 0.06 Uiso calc U . R 1 . .
C C2 0.9554(3) 0.4862(16) 0.4158(5) 0.047(2) Uani d U . G 1 . .
C C3 0.8773(6) 0.5781(16) 0.3506(4) 0.046(2) Uani d U . G 1 . .
H H3 0.9116 0.6373 0.3081 0.055 Uiso calc U . R 1 . .
C C4 0.7492(5) 0.5834(17) 0.3476(4) 0.046(2) Uani d U . G 1 . .
H H4 0.6958 0.6462 0.303 0.055 Uiso calc U . R 1 . .
C C5 0.6992(3) 0.497(2) 0.4097(5) 0.046(2) Uani d U . DG 1 . .
C C6 0.7773(6) 0.4049(18) 0.4749(4) 0.046(2) Uani d U . G 1 . .
H H6 0.743 0.3457 0.5174 0.056 Uiso calc U . R 1 . .
C C7 0.9054(5) 0.3996(16) 0.4779(4) 0.046(2) Uani d U . G 1 . .
H H7 0.9588 0.3368 0.5225 0.055 Uiso calc U . R 1 . .
C C8 0.4656(5) 0.5171(17) 0.3307(3) 0.049(2) Uani d U . DG 1 . .
C C9 0.4837(5) 0.4320(16) 0.2571(4) 0.048(2) Uani d U . G 1 . .
H H9 0.5624 0.3793 0.2552 0.058 Uiso calc U . R 1 . .
C C10 0.3868(7) 0.4241(17) 0.1864(4) 0.049(2) Uani d U . G 1 . .
H H10 0.3991 0.366 0.1361 0.059 Uiso calc U . R 1 . .
C C11 0.2717(6) 0.5012(19) 0.1892(4) 0.049(2) Uani d U . G 1 . .
C C12 0.2535(5) 0.5863(17) 0.2628(5) 0.047(2) Uani d U . G 1 . .
H H12 0.1749 0.639 0.2647 0.057 Uiso calc U . R 1 . .
C C13 0.3505(6) 0.5942(16) 0.3335(3) 0.047(2) Uani d U . G 1 . .
H H13 0.3381 0.6524 0.3838 0.056 Uiso calc U . R 1 . .
C C1 1.1662(14) 0.404(3) 0.4821(9) 0.057(4) Uani d U . . 1 . .
H H1A 1.1589 0.4583 0.5365 0.086 Uiso calc U . R 1 . .
H H1B 1.2521 0.4184 0.4736 0.086 Uiso calc U . R 1 . .
H H1C 1.1454 0.2764 0.4823 0.086 Uiso calc U . R 1 . .
C C14 0.1806(17) 0.392(3) 0.0513(10) 0.076(5) Uani d U . . 1 . .
H H14A 0.2552 0.43 0.0307 0.114 Uiso calc U . R 1 . .
H H14B 0.1063 0.4101 0.0064 0.114 Uiso calc U . R 1 . .
H H14C 0.188 0.265 0.0671 0.114 Uiso calc U . R 1 . .
C C21 -0.2227(15) 0.594(3) 0.7035(10) 0.063(4) Uani d U . . 1 . .
H H21A -0.1978 0.72 0.7003 0.095 Uiso calc U . R 1 . .
H H21B -0.3075 0.5884 0.715 0.095 Uiso calc U . R 1 . .
H H21C -0.2211 0.5342 0.6494 0.095 Uiso calc U . R 1 . .
C C28 0.8536(16) 0.413(3) 1.0883(11) 0.075(5) Uani d U . . 1 . .
H H28A 0.8484 0.2839 1.0763 0.113 Uiso calc U . R 1 . .
H H28B 0.9025 0.433 1.1458 0.113 Uiso calc U . R 1 . .
H H28C 0.8942 0.4737 1.047 0.113 Uiso calc U . R 1 . .
C C29 0.3809(2) 0.494(2) 0.7702(2) 0.048(3) Uani d U . D 1 . .
C C30 0.4192(6) 0.499(3) 0.6970(2) 0.048(2) Uani d U . D 1 . .
C C31 0.4546(5) 0.502(3) 0.62644(17) 0.048(2) Uani d U . D 1 . .
C C32 0.4905(5) 0.507(3) 0.55604(17) 0.049(2) Uani d U . D 1 . .
C C33 0.5273(6) 0.508(3) 0.4859(2) 0.049(2) Uani d U . D 1 . .
C C34 0.5624(2) 0.5075(17) 0.4114(2) 0.047(3) Uani d U . D 1 . .
O O1 0.1695(9) 0.497(2) 0.1234(6) 0.060(3) Uani d U . . 1 . .
O O2 -0.1369(9) 0.505(2) 0.7710(6) 0.056(3) Uani d U . . 1 . .
O O3 0.7317(10) 0.483(2) 1.0825(6) 0.063(3) Uani d U . . 1 . .
O O4 1.0798(8) 0.4945(19) 0.4130(5) 0.049(2) Uani d U . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C22 C23 . 1.39 ?
C22 C27 . 1.39 ?
C22 C29 . 1.5 ?
C23 C24 . 1.39 ?
C23 H23 . 0.95 ?
C24 C25 . 1.39 ?
C24 H24 . 0.95 ?
C25 C26 . 1.39 ?
C25 O3 . 1.391(10) ?
C26 C27 . 1.39 ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C15 C16 . 1.39 ?
C15 C20 . 1.39 ?
C15 C29 . 1.5 ?
C16 C17 . 1.39 ?
C16 H16 . 0.95 ?
C17 C18 . 1.39 ?
C17 H17 . 0.95 ?
C18 O2 . 1.379(10) ?
C18 C19 . 1.39 ?
C19 C20 . 1.39 ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C2 O4 . 1.368(9) ?
C2 C3 . 1.39 ?
C2 C7 . 1.39 ?
C3 C4 . 1.39 ?
C3 H3 . 0.95 ?
C4 C5 . 1.39 ?
C4 H4 . 0.95 ?
C5 C6 . 1.39 ?
C5 C34 . 1.5 ?
C6 C7 . 1.39 ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C8 C9 . 1.39 ?
C8 C13 . 1.39 ?
C8 C34 . 1.5 ?
C9 C10 . 1.39 ?
C9 H9 . 0.95 ?
C10 C11 . 1.39 ?
C10 H10 . 0.95 ?
C11 O1 . 1.374(10) ?
C11 C12 . 1.39 ?
C12 C13 . 1.39 ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C1 O4 . 1.465(16) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C14 O1 . 1.420(19) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C21 O2 . 1.443(17) ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C28 O3 . 1.415(19) ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 C30 . 1.325(4) ?
C30 C31 . 1.2700(4) ?
C31 C32 . 1.2700(4) ?
C32 C33 . 1.2700(4) ?
C33 C34 . 1.330(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 C22 C27 . . 120.0 ?
C23 C22 C29 . . 119.7(6) ?
C27 C22 C29 . . 120.2(6) ?
C22 C23 C24 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C24 C23 H23 . . 120.0 ?
C23 C24 C25 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C25 C24 H24 . . 120.0 ?
C26 C25 C24 . . 120.0 ?
C26 C25 O3 . . 115.6(8) ?
C24 C25 O3 . . 124.4(8) ?
C27 C26 C25 . . 120.0 ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
C26 C27 C22 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C22 C27 H27 . . 120.0 ?
C16 C15 C20 . . 120.0 ?
C16 C15 C29 . . 121.8(8) ?
C20 C15 C29 . . 118.2(7) ?
C17 C16 C15 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C18 C17 C16 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
O2 C18 C17 . . 115.2(8) ?
O2 C18 C19 . . 124.8(8) ?
C17 C18 C19 . . 120.0 ?
C20 C19 C18 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C15 C20 H20 . . 120.0 ?
O4 C2 C3 . . 114.5(7) ?
O4 C2 C7 . . 125.4(7) ?
C3 C2 C7 . . 120.0 ?
C2 C3 C4 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.0 ?
C4 C5 C34 . . 121.6(7) ?
C6 C5 C34 . . 118.3(7) ?
C7 C6 C5 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C2 C7 H7 . . 120.0 ?
C9 C8 C13 . . 120.0 ?
C9 C8 C34 . . 121.2(7) ?
C13 C8 C34 . . 118.4(6) ?
C8 C9 C10 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C11 C10 C9 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
O1 C11 C10 . . 124.3(7) ?
O1 C11 C12 . . 115.7(7) ?
C10 C11 C12 . . 120.0 ?
C13 C12 C11 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C8 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
O4 C1 H1A . . 109.5 ?
O4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O2 C21 H21A . . 109.5 ?
O2 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O2 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O3 C28 H28A . . 109.5 ?
O3 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
O3 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C30 C29 C22 . . 120.5(4) ?
C30 C29 C15 . . 120.5(5) ?
C22 C29 C15 . . 119.0(4) ?
C31 C30 C29 . . 179.2(15) ?
C30 C31 C32 . . 179.6(17) ?
C33 C32 C31 . . 178.7(19) ?
C32 C33 C34 . . 178.3(8) ?
C33 C34 C8 . . 119.9(4) ?
C33 C34 C5 . . 118.9(5) ?
C8 C34 C5 . . 121.1(5) ?
C11 O1 C14 . . 116.9(12) ?
C18 O2 C21 . . 116.9(11) ?
C25 O3 C28 . . 118.2(11) ?
C2 O4 C1 . . 116.5(10) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C27 C22 C23 C24 . . . . 0 ?
C29 C22 C23 C24 . . . . 177.5(12) ?
C22 C23 C24 C25 . . . . 0 ?
C23 C24 C25 C26 . . . . 0 ?
C23 C24 C25 O3 . . . . 178.3(12) ?
C24 C25 C26 C27 . . . . 0 ?
O3 C25 C26 C27 . . . . -178.4(11) ?
C25 C26 C27 C22 . . . . 0 ?
C23 C22 C27 C26 . . . . 0 ?
C29 C22 C27 C26 . . . . -177.5(12) ?
C20 C15 C16 C17 . . . . 0 ?
C29 C15 C16 C17 . . . . -177.4(11) ?
C15 C16 C17 C18 . . . . 0 ?
C16 C17 C18 O2 . . . . -177.4(11) ?
C16 C17 C18 C19 . . . . 0 ?
O2 C18 C19 C20 . . . . 177.1(12) ?
C17 C18 C19 C20 . . . . 0 ?
C18 C19 C20 C15 . . . . 0 ?
C16 C15 C20 C19 . . . . 0 ?
C29 C15 C20 C19 . . . . 177.5(11) ?
O4 C2 C3 C4 . . . . -178.4(10) ?
C7 C2 C3 C4 . . . . 0 ?
C2 C3 C4 C5 . . . . 0 ?
C3 C4 C5 C6 . . . . 0 ?
C3 C4 C5 C34 . . . . 176.7(12) ?
C4 C5 C6 C7 . . . . 0 ?
C34 C5 C6 C7 . . . . -176.8(12) ?
C5 C6 C7 C2 . . . . 0 ?
O4 C2 C7 C6 . . . . 178.3(11) ?
C3 C2 C7 C6 . . . . 0 ?
C13 C8 C9 C10 . . . . 0 ?
C34 C8 C9 C10 . . . . 172.1(11) ?
C8 C9 C10 C11 . . . . 0 ?
C9 C10 C11 O1 . . . . -178.4(13) ?
C9 C10 C11 C12 . . . . 0 ?
O1 C11 C12 C13 . . . . 178.5(12) ?
C10 C11 C12 C13 . . . . 0 ?
C11 C12 C13 C8 . . . . 0 ?
C9 C8 C13 C12 . . . . 0 ?
C34 C8 C13 C12 . . . . -172.3(12) ?
C23 C22 C29 C30 . . . . -30.(2) ?
C27 C22 C29 C30 . . . . 147.7(15) ?
C23 C22 C29 C15 . . . . 151.4(11) ?
C27 C22 C29 C15 . . . . -31.1(19) ?
C16 C15 C29 C30 . . . . 141.0(15) ?
C20 C15 C29 C30 . . . . -36.(2) ?
C16 C15 C29 C22 . . . . -40.1(19) ?
C20 C15 C29 C22 . . . . 142.5(12) ?
C9 C8 C34 C33 . . . . -147.5(14) ?
C13 C8 C34 C33 . . . . 25.(2) ?
C9 C8 C34 C5 . . . . 32.(2) ?
C13 C8 C34 C5 . . . . -155.5(12) ?
C4 C5 C34 C33 . . . . -146.3(14) ?
C6 C5 C34 C33 . . . . 30.(2) ?
C4 C5 C34 C8 . . . . 34.(2) ?
C6 C5 C34 C8 . . . . -149.3(12) ?
C10 C11 O1 C14 . . . . 6.(2) ?
C12 C11 O1 C14 . . . . -172.7(13) ?
C17 C18 O2 C21 . . . . -171.8(11) ?
C19 C18 O2 C21 . . . . 10.9(18) ?
C26 C25 O3 C28 . . . . -175.4(13) ?
C24 C25 O3 C28 . . . . 6.2(19) ?
C3 C2 O4 C1 . . . . 178.1(11) ?
C7 C2 O4 C1 . . . . -0.3(17) ?


####################################################################### 
# 
# 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_yasuda20191211
_database_code_depnum_ccdc_archive 'CCDC 2089132'
loop_
_audit_author_name
_audit_author_address
'Fumitoshi Yagishita'
;Tokushima University
Japan
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C34 H29 I O4'
_chemical_formula_moiety         'C34 H29 I O4'
_chemical_formula_weight         628.51
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.24137(19)
_cell_length_b                   11.9283(2)
_cell_length_c                   13.3381(2)
_cell_angle_alpha                113.529(8)
_cell_angle_beta                 109.913(8)
_cell_angle_gamma                93.193(7)
_cell_volume                     1369.46(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16080
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      68.34
_cell_measurement_temperature    104
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.068
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636.00
_exptl_absorpt_coefficient_mu    9.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_T_max  0.524

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      104
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15911
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.937
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4921
_reflns_number_gt                4816
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0915
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4921
_refine_ls_number_parameters     356
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0480P)²+2.5835P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         1.39
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.3257 6.8362
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
I1 I 0.95955(2) 0.76793(2) 1.42778(2) 0.02256(9) Uani 1 1 d . . . . .
O1 O 0.3197(3) -0.0019(2) 0.7606(2) 0.0252(5) Uani 1 1 d . . . . .
O2 O 0.5487(2) 0.3555(2) 1.4796(2) 0.0207(5) Uani 1 1 d . . . . .
O3 O 0.7083(3) 0.0055(2) 0.5961(2) 0.0214(5) Uani 1 1 d . . . . .
O35 O 0.9261(3) 0.9031(2) 0.8413(2) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.8665(3) 0.6293(3) 1.2525(3) 0.0135(6) Uani 1 1 d . . . . .
C3 C 0.7974(3) 0.4713(3) 1.3869(3) 0.0164(6) Uani 1 1 d . . . . .
H3 H 0.8977 0.4981 1.4156 0.020 Uiso 1 1 calc R U . . .
C4 C 0.8355(3) 0.6052(3) 0.9138(3) 0.0125(6) Uani 1 1 d . . . . .
C5 C 0.5050(3) 0.3939(3) 1.3060(3) 0.0157(6) Uani 1 1 d . . . . .
H5 H 0.4047 0.3679 1.2783 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5628(3) 0.4331(3) 1.2426(3) 0.0153(6) Uani 1 1 d . . . . .
H6 H 0.5007 0.4336 1.1713 0.018 Uiso 1 1 calc R U . . .
C7 C 0.7886(3) 0.1558(3) 0.7945(3) 0.0153(6) Uani 1 1 d . . . . .
H7 H 0.8156 0.0922 0.8178 0.018 Uiso 1 1 calc R U . . .
C8 C 0.7094(3) 0.4718(3) 1.2798(3) 0.0134(6) Uani 1 1 d . . . . .
C9 C 0.7037(3) 0.3403(3) 0.7269(3) 0.0148(6) Uani 1 1 d . . . . .
H9 H 0.6724 0.4027 0.7031 0.018 Uiso 1 1 calc R U . . .
C10 C 0.9066(3) 0.5923(3) 0.8380(3) 0.0140(6) Uani 1 1 d . . . . .
H10 H 0.9327 0.5152 0.8034 0.017 Uiso 1 1 calc R U . . .
C11 C 0.4030(3) 0.2130(3) 0.8337(3) 0.0174(6) Uani 1 1 d . . . . .
H11 H 0.3212 0.2112 0.7715 0.021 Uiso 1 1 calc R U . . .
C12 C 0.7696(3) 0.3726(3) 0.8486(3) 0.0127(6) Uani 1 1 d . . . . .
C13 C 0.8010(3) 0.5281(3) 1.0526(3) 0.0123(6) Uani 1 1 d . . . . .
C14 C 0.5940(3) 0.3928(3) 1.4102(3) 0.0155(6) Uani 1 1 d . . . . .
C15 C 0.5015(3) 0.3250(3) 0.9134(3) 0.0155(6) Uani 1 1 d . . . . .
H15 H 0.4869 0.3991 0.9048 0.019 Uiso 1 1 calc R U . . .
C16 C 0.8831(3) 0.6421(3) 1.1610(3) 0.0133(6) Uani 1 1 d . . . . .
H16 H 0.9382 0.7126 1.1664 0.016 Uiso 1 1 calc R U . . .
C17 C 0.7408(3) 0.4328(3) 1.4511(3) 0.0169(6) Uani 1 1 d . . . . .
H17 H 0.8021 0.4335 1.5233 0.020 Uiso 1 1 calc R U . . .
C18 C 0.6220(3) 0.3302(3) 1.0064(3) 0.0134(6) Uani 1 1 d . . . . .
C19 C 0.8001(3) 0.5017(3) 0.9414(3) 0.0127(6) Uani 1 1 d . . . . .
C20 C 0.7975(3) 0.7202(3) 0.9622(3) 0.0150(6) Uani 1 1 d . . . . .
H20 H 0.7483 0.7315 1.0132 0.018 Uiso 1 1 calc R U . . .
C21 C 0.8119(3) 0.2762(3) 0.8793(3) 0.0132(6) Uani 1 1 d . . . . .
H21 H 0.8578 0.2953 0.9610 0.016 Uiso 1 1 calc R U . . .
C22 C 0.6831(3) 0.2200(3) 0.6406(3) 0.0158(6) Uani 1 1 d . . . . .
H22 H 0.6404 0.2009 0.5586 0.019 Uiso 1 1 calc R U . . .
C23 C 0.7299(3) 0.4487(3) 1.0883(3) 0.0129(6) Uani 1 1 d . . . . .
C24 C 0.5418(4) 0.1070(3) 0.9368(3) 0.0193(7) Uani 1 1 d . . . . .
H24 H 0.5562 0.0326 0.9449 0.023 Uiso 1 1 calc R U . . .
C25 C 0.9016(3) 0.8023(3) 0.8620(3) 0.0164(6) Uani 1 1 d . . . . .
C26 C 0.8304(4) 0.8171(3) 0.9371(3) 0.0176(6) Uani 1 1 d . . . . .
H26 H 0.8043 0.8944 0.9712 0.021 Uiso 1 1 calc R U . . .
C27 C 0.7680(3) 0.5114(3) 1.2097(3) 0.0135(6) Uani 1 1 d . . . . .
C28 C 0.9398(3) 0.6894(3) 0.8124(3) 0.0157(6) Uani 1 1 d . . . . .
H28 H 0.9885 0.6787 0.7612 0.019 Uiso 1 1 calc R U . . .
C29 C 0.7251(3) 0.1267(3) 0.6739(3) 0.0155(6) Uani 1 1 d . . . . .
C30 C 0.6392(3) 0.2204(3) 1.0173(3) 0.0168(6) Uani 1 1 d . . . . .
H30 H 0.7194 0.2227 1.0811 0.020 Uiso 1 1 calc R U . . .
C31 C 0.4227(3) 0.1038(3) 0.8440(3) 0.0178(7) Uani 1 1 d . . . . .
C32 C 0.4011(4) 0.2987(3) 1.4339(3) 0.0229(7) Uani 1 1 d . . . . .
H32A H 0.3763 0.2221 1.3597 0.028 Uiso 1 1 calc R U . . .
H32B H 0.3433 0.3573 1.4183 0.028 Uiso 1 1 calc R U . . .
H32C H 0.3825 0.2777 1.4925 0.028 Uiso 1 1 calc R U . . .
C33 C 0.3604(4) -0.1190(3) 0.7378(4) 0.0302(8) Uani 1 1 d . . . . .
H33A H 0.4483 -0.1156 0.7240 0.036 Uiso 1 1 calc R U . . .
H33B H 0.2845 -0.1859 0.6672 0.036 Uiso 1 1 calc R U . . .
H33C H 0.3765 -0.1360 0.8066 0.036 Uiso 1 1 calc R U . . .
C34 C 0.6662(4) -0.0237(3) 0.4730(3) 0.0235(7) Uani 1 1 d . . . . .
H34A H 0.5724 -0.0055 0.4433 0.028 Uiso 1 1 calc R U . . .
H34B H 0.6614 -0.1128 0.4273 0.028 Uiso 1 1 calc R U . . .
H34C H 0.7361 0.0272 0.4641 0.028 Uiso 1 1 calc R U . . .
C36 C 0.9966(5) 0.8922(4) 0.7631(4) 0.0314(9) Uani 1 1 d . . . . .
H36A H 1.0061 0.9702 0.7551 0.038 Uiso 1 1 calc R U . . .
H36B H 0.9406 0.8222 0.6847 0.038 Uiso 1 1 calc R U . . .
H36C H 1.0913 0.8769 0.7958 0.038 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
I1 C2 2.081(3) . ?
O1 C31 1.369(4) . ?
O1 C33 1.424(4) . ?
O2 C14 1.366(4) . ?
O2 C32 1.430(4) . ?
O3 C29 1.360(4) . ?
O3 C34 1.432(4) . ?
O35 C25 1.365(4) . ?
O35 C36 1.429(4) . ?
C2 C16 1.352(4) . ?
C2 C27 1.459(4) . ?
C3 C17 1.379(5) . ?
C3 C8 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C10 1.401(4) . ?
C4 C20 1.405(4) . ?
C4 C19 1.482(4) . ?
C5 C6 1.383(4) . ?
C5 C14 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C8 1.395(4) . ?
C6 H6 0.9500 . ?
C7 C21 1.372(5) . ?
C7 C29 1.395(4) . ?
C7 H7 0.9500 . ?
C8 C27 1.470(4) . ?
C9 C22 1.383(5) . ?
C9 C12 1.402(4) . ?
C9 H9 0.9500 . ?
C10 C28 1.387(4) . ?
C10 H10 0.9500 . ?
C11 C31 1.381(5) . ?
C11 C15 1.385(5) . ?
C11 H11 0.9500 . ?
C12 C21 1.409(4) . ?
C12 C19 1.471(4) . ?
C13 C19 1.385(4) . ?
C13 C16 1.456(4) . ?
C13 C23 1.473(4) . ?
C14 C17 1.392(5) . ?
C15 C18 1.398(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C30 1.388(4) . ?
C18 C23 1.477(4) . ?
C20 C26 1.380(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C29 1.392(4) . ?
C22 H22 0.9500 . ?
C23 C27 1.379(4) . ?
C24 C30 1.392(5) . ?
C24 C31 1.396(5) . ?
C24 H24 0.9500 . ?
C25 C28 1.388(5) . ?
C25 C26 1.391(5) . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
C30 H30 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C31 O1 C33 116.9(3) . . ?
C14 O2 C32 117.7(2) . . ?
C29 O3 C34 117.6(2) . . ?
C25 O35 C36 117.8(3) . . ?
C16 C2 C27 110.9(3) . . ?
C16 C2 I1 123.2(2) . . ?
C27 C2 I1 125.8(2) . . ?
C17 C3 C8 121.3(3) . . ?
C17 C3 H3 119.3 . . ?
C8 C3 H3 119.3 . . ?
C10 C4 C20 117.4(3) . . ?
C10 C4 C19 121.7(3) . . ?
C20 C4 C19 120.9(3) . . ?
C6 C5 C14 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C14 C5 H5 120.2 . . ?
C5 C6 C8 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C8 C6 H6 118.9 . . ?
C21 C7 C29 120.0(3) . . ?
C21 C7 H7 120.0 . . ?
C29 C7 H7 120.0 . . ?
C6 C8 C3 117.0(3) . . ?
C6 C8 C27 121.0(3) . . ?
C3 C8 C27 122.0(3) . . ?
C22 C9 C12 121.6(3) . . ?
C22 C9 H9 119.2 . . ?
C12 C9 H9 119.2 . . ?
C28 C10 C4 121.6(3) . . ?
C28 C10 H10 119.2 . . ?
C4 C10 H10 119.2 . . ?
C31 C11 C15 120.6(3) . . ?
C31 C11 H11 119.7 . . ?
C15 C11 H11 119.7 . . ?
C9 C12 C21 117.0(3) . . ?
C9 C12 C19 122.3(3) . . ?
C21 C12 C19 120.6(3) . . ?
C19 C13 C16 124.7(3) . . ?
C19 C13 C23 128.9(3) . . ?
C16 C13 C23 106.3(3) . . ?
O2 C14 C5 124.6(3) . . ?
O2 C14 C17 115.6(3) . . ?
C5 C14 C17 119.7(3) . . ?
C11 C15 C18 120.8(3) . . ?
C11 C15 H15 119.6 . . ?
C18 C15 H15 119.6 . . ?
C2 C16 C13 107.5(3) . . ?
C2 C16 H16 126.2 . . ?
C13 C16 H16 126.2 . . ?
C3 C17 C14 120.1(3) . . ?
C3 C17 H17 119.9 . . ?
C14 C17 H17 119.9 . . ?
C30 C18 C15 118.1(3) . . ?
C30 C18 C23 121.2(3) . . ?
C15 C18 C23 120.6(3) . . ?
C13 C19 C12 122.3(3) . . ?
C13 C19 C4 120.1(3) . . ?
C12 C19 C4 117.6(3) . . ?
C26 C20 C4 121.2(3) . . ?
C26 C20 H20 119.4 . . ?
C4 C20 H20 119.4 . . ?
C7 C21 C12 121.9(3) . . ?
C7 C21 H21 119.1 . . ?
C12 C21 H21 119.1 . . ?
C9 C22 C29 119.9(3) . . ?
C9 C22 H22 120.0 . . ?
C29 C22 H22 120.0 . . ?
C27 C23 C13 108.3(3) . . ?
C27 C23 C18 125.6(3) . . ?
C13 C23 C18 125.8(3) . . ?
C30 C24 C31 119.3(3) . . ?
C30 C24 H24 120.4 . . ?
C31 C24 H24 120.4 . . ?
O35 C25 C28 124.9(3) . . ?
O35 C25 C26 115.4(3) . . ?
C28 C25 C26 119.7(3) . . ?
C20 C26 C25 120.3(3) . . ?
C20 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C23 C27 C2 106.9(3) . . ?
C23 C27 C8 126.1(3) . . ?
C2 C27 C8 126.7(3) . . ?
C10 C28 C25 119.8(3) . . ?
C10 C28 H28 120.1 . . ?
C25 C28 H28 120.1 . . ?
O3 C29 C22 124.5(3) . . ?
O3 C29 C7 115.9(3) . . ?
C22 C29 C7 119.6(3) . . ?
C18 C30 C24 121.6(3) . . ?
C18 C30 H30 119.2 . . ?
C24 C30 H30 119.2 . . ?
O1 C31 C11 116.1(3) . . ?
O1 C31 C24 124.3(3) . . ?
C11 C31 C24 119.6(3) . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O1 C33 H33A 109.5 . . ?
O1 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O1 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O3 C34 H34A 109.5 . . ?
O3 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O3 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O35 C36 H36A 109.5 . . ?
O35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C14 C5 C6 C8 0.1(5) . . . . ?
C5 C6 C8 C3 -0.9(5) . . . . ?
C5 C6 C8 C27 179.1(3) . . . . ?
C17 C3 C8 C6 0.7(5) . . . . ?
C17 C3 C8 C27 -179.3(3) . . . . ?
C20 C4 C10 C28 0.6(4) . . . . ?
C19 C4 C10 C28 -179.9(3) . . . . ?
C22 C9 C12 C21 -1.0(4) . . . . ?
C22 C9 C12 C19 176.2(3) . . . . ?
C32 O2 C14 C5 8.4(5) . . . . ?
C32 O2 C14 C17 -172.1(3) . . . . ?
C6 C5 C14 O2 -179.7(3) . . . . ?
C6 C5 C14 C17 0.9(5) . . . . ?
C31 C11 C15 C18 -0.6(5) . . . . ?
C27 C2 C16 C13 -3.1(3) . . . . ?
I1 C2 C16 C13 -178.94(19) . . . . ?
C19 C13 C16 C2 -174.8(3) . . . . ?
C23 C13 C16 C2 2.1(3) . . . . ?
C8 C3 C17 C14 0.2(5) . . . . ?
O2 C14 C17 C3 179.4(3) . . . . ?
C5 C14 C17 C3 -1.1(5) . . . . ?
C11 C15 C18 C30 -0.7(4) . . . . ?
C11 C15 C18 C23 177.4(3) . . . . ?
C16 C13 C19 C12 153.3(3) . . . . ?
C23 C13 C19 C12 -22.8(5) . . . . ?
C16 C13 C19 C4 -24.5(4) . . . . ?
C23 C13 C19 C4 159.3(3) . . . . ?
C9 C12 C19 C13 149.2(3) . . . . ?
C21 C12 C19 C13 -33.6(4) . . . . ?
C9 C12 C19 C4 -32.9(4) . . . . ?
C21 C12 C19 C4 144.3(3) . . . . ?
C10 C4 C19 C13 146.3(3) . . . . ?
C20 C4 C19 C13 -34.2(4) . . . . ?
C10 C4 C19 C12 -31.6(4) . . . . ?
C20 C4 C19 C12 147.8(3) . . . . ?
C10 C4 C20 C26 -0.7(4) . . . . ?
C19 C4 C20 C26 179.9(3) . . . . ?
C29 C7 C21 C12 1.9(5) . . . . ?
C9 C12 C21 C7 -0.7(4) . . . . ?
C19 C12 C21 C7 -178.0(3) . . . . ?
C12 C9 C22 C29 1.6(5) . . . . ?
C19 C13 C23 C27 176.4(3) . . . . ?
C16 C13 C23 C27 -0.3(3) . . . . ?
C19 C13 C23 C18 -10.8(5) . . . . ?
C16 C13 C23 C18 172.5(3) . . . . ?
C30 C18 C23 C27 -62.8(4) . . . . ?
C15 C18 C23 C27 119.2(3) . . . . ?
C30 C18 C23 C13 125.6(3) . . . . ?
C15 C18 C23 C13 -52.4(4) . . . . ?
C36 O35 C25 C28 -0.1(5) . . . . ?
C36 O35 C25 C26 -178.9(3) . . . . ?
C4 C20 C26 C25 0.4(5) . . . . ?
O35 C25 C26 C20 178.7(3) . . . . ?
C28 C25 C26 C20 -0.1(5) . . . . ?
C13 C23 C27 C2 -1.5(3) . . . . ?
C18 C23 C27 C2 -174.3(3) . . . . ?
C13 C23 C27 C8 173.1(3) . . . . ?
C18 C23 C27 C8 0.3(5) . . . . ?
C16 C2 C27 C23 3.0(3) . . . . ?
I1 C2 C27 C23 178.6(2) . . . . ?
C16 C2 C27 C8 -171.6(3) . . . . ?
I1 C2 C27 C8 4.1(4) . . . . ?
C6 C8 C27 C23 -47.1(4) . . . . ?
C3 C8 C27 C23 133.0(3) . . . . ?
C6 C8 C27 C2 126.4(3) . . . . ?
C3 C8 C27 C2 -53.5(4) . . . . ?
C4 C10 C28 C25 -0.3(5) . . . . ?
O35 C25 C28 C10 -178.6(3) . . . . ?
C26 C25 C28 C10 0.1(5) . . . . ?
C34 O3 C29 C22 10.6(5) . . . . ?
C34 O3 C29 C7 -169.7(3) . . . . ?
C9 C22 C29 O3 179.3(3) . . . . ?
C9 C22 C29 C7 -0.4(5) . . . . ?
C21 C7 C29 O3 178.9(3) . . . . ?
C21 C7 C29 C22 -1.3(5) . . . . ?
C15 C18 C30 C24 1.5(5) . . . . ?
C23 C18 C30 C24 -176.6(3) . . . . ?
C31 C24 C30 C18 -1.0(5) . . . . ?
C33 O1 C31 C11 155.6(3) . . . . ?
C33 O1 C31 C24 -25.2(5) . . . . ?
C15 C11 C31 O1 -179.7(3) . . . . ?
C15 C11 C31 C24 1.1(5) . . . . ?
C30 C24 C31 O1 -179.4(3) . . . . ?
C30 C24 C31 C11 -0.3(5) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2089167'
loop_
_audit_author_name
_audit_author_address
'Fumitoshi Yagishita'
;Tokushima University
Japan
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         500.56
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.913(4)
_cell_length_b                   7.442(3)
_cell_length_c                   16.072(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.62(3)
_cell_angle_gamma                90
_cell_volume                     1278.5(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    384
_cell_measurement_theta_min      4.1358
_cell_measurement_theta_max      50.3131
_cell_measurement_temperature    173(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528

_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173(2)

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5392
_diffrn_reflns_av_R_equivalents  0.1406
_diffrn_reflns_av_unetI/netI     0.2838
_diffrn_reflns_theta_min         2.807
_diffrn_reflns_theta_max         66.605
_diffrn_reflns_theta_full        66.605
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3532
_reflns_number_gt                1420
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2178
_refine_ls_R_factor_gt           0.1184
_refine_ls_wR_factor_gt          0.2748
_refine_ls_wR_factor_ref         0.3523
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.892
_refine_ls_number_reflns         3532
_refine_ls_number_parameters     299
_refine_ls_number_restraints     493
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.1678P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.509
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 194 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C22 0.4739(5) 0.4856(17) 0.8527(2) 0.046(2) Uani d U . DG 1 . .
C C23 0.5890(6) 0.4029(16) 0.8558(4) 0.046(2) Uani d U . G 1 . .
H H23 0.6072 0.3477 0.8064 0.056 Uiso calc U . R 1 . .
C C24 0.6775(5) 0.4011(17) 0.9313(5) 0.049(2) Uani d U . G 1 . .
H H24 0.7561 0.3446 0.9335 0.059 Uiso calc U . R 1 . .
C C25 0.6509(7) 0.4820(18) 1.0036(3) 0.049(2) Uani d U . G 1 . .
C C26 0.5358(8) 0.5646(17) 1.0004(3) 0.049(2) Uani d U . G 1 . .
H H26 0.5176 0.6199 1.0498 0.059 Uiso calc U . R 1 . .
C C27 0.4473(6) 0.5664(16) 0.9250(4) 0.047(2) Uani d U . G 1 . .
H H27 0.3687 0.6229 0.9228 0.056 Uiso calc U . R 1 . .
C C15 0.2440(3) 0.4992(19) 0.7718(5) 0.048(2) Uani d U . DG 1 . .
C C16 0.1931(6) 0.3960(17) 0.8284(4) 0.049(2) Uani d U . G 1 . .
H H16 0.2459 0.3231 0.8692 0.058 Uiso calc U . R 1 . .
C C17 0.0650(6) 0.3994(17) 0.8255(5) 0.051(2) Uani d U . G 1 . .
H H17 0.0302 0.3288 0.8643 0.061 Uiso calc U . R 1 . .
C C18 -0.0123(3) 0.5060(19) 0.7660(6) 0.050(2) Uani d U . G 1 . .
C C19 0.0386(6) 0.6092(17) 0.7093(5) 0.050(2) Uani d U . G 1 . .
H H19 -0.0142 0.6821 0.6686 0.06 Uiso calc U . R 1 . .
C C20 0.1668(6) 0.6058(17) 0.7122(5) 0.050(2) Uani d U . G 1 . .
H H20 0.2015 0.6764 0.6734 0.06 Uiso calc U . R 1 . .
C C2 0.9554(3) 0.4862(16) 0.4158(5) 0.047(2) Uani d U . G 1 . .
C C3 0.8773(6) 0.5781(16) 0.3506(4) 0.046(2) Uani d U . G 1 . .
H H3 0.9116 0.6373 0.3081 0.055 Uiso calc U . R 1 . .
C C4 0.7492(5) 0.5834(17) 0.3476(4) 0.046(2) Uani d U . G 1 . .
H H4 0.6958 0.6462 0.303 0.055 Uiso calc U . R 1 . .
C C5 0.6992(3) 0.497(2) 0.4097(5) 0.046(2) Uani d U . DG 1 . .
C C6 0.7773(6) 0.4049(18) 0.4749(4) 0.046(2) Uani d U . G 1 . .
H H6 0.743 0.3457 0.5174 0.056 Uiso calc U . R 1 . .
C C7 0.9054(5) 0.3996(16) 0.4779(4) 0.046(2) Uani d U . G 1 . .
H H7 0.9588 0.3368 0.5225 0.055 Uiso calc U . R 1 . .
C C8 0.4656(5) 0.5171(17) 0.3307(3) 0.049(2) Uani d U . DG 1 . .
C C9 0.4837(5) 0.4320(16) 0.2571(4) 0.048(2) Uani d U . G 1 . .
H H9 0.5624 0.3793 0.2552 0.058 Uiso calc U . R 1 . .
C C10 0.3868(7) 0.4241(17) 0.1864(4) 0.049(2) Uani d U . G 1 . .
H H10 0.3991 0.366 0.1361 0.059 Uiso calc U . R 1 . .
C C11 0.2717(6) 0.5012(19) 0.1892(4) 0.049(2) Uani d U . G 1 . .
C C12 0.2535(5) 0.5863(17) 0.2628(5) 0.047(2) Uani d U . G 1 . .
H H12 0.1749 0.639 0.2647 0.057 Uiso calc U . R 1 . .
C C13 0.3505(6) 0.5942(16) 0.3335(3) 0.047(2) Uani d U . G 1 . .
H H13 0.3381 0.6524 0.3838 0.056 Uiso calc U . R 1 . .
C C1 1.1662(14) 0.404(3) 0.4821(9) 0.057(4) Uani d U . . 1 . .
H H1A 1.1589 0.4583 0.5365 0.086 Uiso calc U . R 1 . .
H H1B 1.2521 0.4184 0.4736 0.086 Uiso calc U . R 1 . .
H H1C 1.1454 0.2764 0.4823 0.086 Uiso calc U . R 1 . .
C C14 0.1806(17) 0.392(3) 0.0513(10) 0.076(5) Uani d U . . 1 . .
H H14A 0.2552 0.43 0.0307 0.114 Uiso calc U . R 1 . .
H H14B 0.1063 0.4101 0.0064 0.114 Uiso calc U . R 1 . .
H H14C 0.188 0.265 0.0671 0.114 Uiso calc U . R 1 . .
C C21 -0.2227(15) 0.594(3) 0.7035(10) 0.063(4) Uani d U . . 1 . .
H H21A -0.1978 0.72 0.7003 0.095 Uiso calc U . R 1 . .
H H21B -0.3075 0.5884 0.715 0.095 Uiso calc U . R 1 . .
H H21C -0.2211 0.5342 0.6494 0.095 Uiso calc U . R 1 . .
C C28 0.8536(16) 0.413(3) 1.0883(11) 0.075(5) Uani d U . . 1 . .
H H28A 0.8484 0.2839 1.0763 0.113 Uiso calc U . R 1 . .
H H28B 0.9025 0.433 1.1458 0.113 Uiso calc U . R 1 . .
H H28C 0.8942 0.4737 1.047 0.113 Uiso calc U . R 1 . .
C C29 0.3809(2) 0.494(2) 0.7702(2) 0.048(3) Uani d U . D 1 . .
C C30 0.4192(6) 0.499(3) 0.6970(2) 0.048(2) Uani d U . D 1 . .
C C31 0.4546(5) 0.502(3) 0.62644(17) 0.048(2) Uani d U . D 1 . .
C C32 0.4905(5) 0.507(3) 0.55604(17) 0.049(2) Uani d U . D 1 . .
C C33 0.5273(6) 0.508(3) 0.4859(2) 0.049(2) Uani d U . D 1 . .
C C34 0.5624(2) 0.5075(17) 0.4114(2) 0.047(3) Uani d U . D 1 . .
O O1 0.1695(9) 0.497(2) 0.1234(6) 0.060(3) Uani d U . . 1 . .
O O2 -0.1369(9) 0.505(2) 0.7710(6) 0.056(3) Uani d U . . 1 . .
O O3 0.7317(10) 0.483(2) 1.0825(6) 0.063(3) Uani d U . . 1 . .
O O4 1.0798(8) 0.4945(19) 0.4130(5) 0.049(2) Uani d U . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C22 C23 . 1.39 ?
C22 C27 . 1.39 ?
C22 C29 . 1.5 ?
C23 C24 . 1.39 ?
C23 H23 . 0.95 ?
C24 C25 . 1.39 ?
C24 H24 . 0.95 ?
C25 C26 . 1.39 ?
C25 O3 . 1.391(10) ?
C26 C27 . 1.39 ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C15 C16 . 1.39 ?
C15 C20 . 1.39 ?
C15 C29 . 1.5 ?
C16 C17 . 1.39 ?
C16 H16 . 0.95 ?
C17 C18 . 1.39 ?
C17 H17 . 0.95 ?
C18 O2 . 1.379(10) ?
C18 C19 . 1.39 ?
C19 C20 . 1.39 ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C2 O4 . 1.368(9) ?
C2 C3 . 1.39 ?
C2 C7 . 1.39 ?
C3 C4 . 1.39 ?
C3 H3 . 0.95 ?
C4 C5 . 1.39 ?
C4 H4 . 0.95 ?
C5 C6 . 1.39 ?
C5 C34 . 1.5 ?
C6 C7 . 1.39 ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C8 C9 . 1.39 ?
C8 C13 . 1.39 ?
C8 C34 . 1.5 ?
C9 C10 . 1.39 ?
C9 H9 . 0.95 ?
C10 C11 . 1.39 ?
C10 H10 . 0.95 ?
C11 O1 . 1.374(10) ?
C11 C12 . 1.39 ?
C12 C13 . 1.39 ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C1 O4 . 1.465(16) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C14 O1 . 1.420(19) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C21 O2 . 1.443(17) ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C28 O3 . 1.415(19) ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 C30 . 1.325(4) ?
C30 C31 . 1.2700(4) ?
C31 C32 . 1.2700(4) ?
C32 C33 . 1.2700(4) ?
C33 C34 . 1.330(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 C22 C27 . . 120.0 ?
C23 C22 C29 . . 119.7(6) ?
C27 C22 C29 . . 120.2(6) ?
C22 C23 C24 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C24 C23 H23 . . 120.0 ?
C23 C24 C25 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C25 C24 H24 . . 120.0 ?
C26 C25 C24 . . 120.0 ?
C26 C25 O3 . . 115.6(8) ?
C24 C25 O3 . . 124.4(8) ?
C27 C26 C25 . . 120.0 ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
C26 C27 C22 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C22 C27 H27 . . 120.0 ?
C16 C15 C20 . . 120.0 ?
C16 C15 C29 . . 121.8(8) ?
C20 C15 C29 . . 118.2(7) ?
C17 C16 C15 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C18 C17 C16 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
O2 C18 C17 . . 115.2(8) ?
O2 C18 C19 . . 124.8(8) ?
C17 C18 C19 . . 120.0 ?
C20 C19 C18 . . 120.0 ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C15 C20 H20 . . 120.0 ?
O4 C2 C3 . . 114.5(7) ?
O4 C2 C7 . . 125.4(7) ?
C3 C2 C7 . . 120.0 ?
C2 C3 C4 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.0 ?
C4 C5 C34 . . 121.6(7) ?
C6 C5 C34 . . 118.3(7) ?
C7 C6 C5 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C2 C7 H7 . . 120.0 ?
C9 C8 C13 . . 120.0 ?
C9 C8 C34 . . 121.2(7) ?
C13 C8 C34 . . 118.4(6) ?
C8 C9 C10 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C11 C10 C9 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
O1 C11 C10 . . 124.3(7) ?
O1 C11 C12 . . 115.7(7) ?
C10 C11 C12 . . 120.0 ?
C13 C12 C11 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C8 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
O4 C1 H1A . . 109.5 ?
O4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O2 C21 H21A . . 109.5 ?
O2 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O2 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O3 C28 H28A . . 109.5 ?
O3 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
O3 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C30 C29 C22 . . 120.5(4) ?
C30 C29 C15 . . 120.5(5) ?
C22 C29 C15 . . 119.0(4) ?
C31 C30 C29 . . 179.2(15) ?
C30 C31 C32 . . 179.6(17) ?
C33 C32 C31 . . 178.7(19) ?
C32 C33 C34 . . 178.3(8) ?
C33 C34 C8 . . 119.9(4) ?
C33 C34 C5 . . 118.9(5) ?
C8 C34 C5 . . 121.1(5) ?
C11 O1 C14 . . 116.9(12) ?
C18 O2 C21 . . 116.9(11) ?
C25 O3 C28 . . 118.2(11) ?
C2 O4 C1 . . 116.5(10) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C27 C22 C23 C24 . . . . 0 ?
C29 C22 C23 C24 . . . . 177.5(12) ?
C22 C23 C24 C25 . . . . 0 ?
C23 C24 C25 C26 . . . . 0 ?
C23 C24 C25 O3 . . . . 178.3(12) ?
C24 C25 C26 C27 . . . . 0 ?
O3 C25 C26 C27 . . . . -178.4(11) ?
C25 C26 C27 C22 . . . . 0 ?
C23 C22 C27 C26 . . . . 0 ?
C29 C22 C27 C26 . . . . -177.5(12) ?
C20 C15 C16 C17 . . . . 0 ?
C29 C15 C16 C17 . . . . -177.4(11) ?
C15 C16 C17 C18 . . . . 0 ?
C16 C17 C18 O2 . . . . -177.4(11) ?
C16 C17 C18 C19 . . . . 0 ?
O2 C18 C19 C20 . . . . 177.1(12) ?
C17 C18 C19 C20 . . . . 0 ?
C18 C19 C20 C15 . . . . 0 ?
C16 C15 C20 C19 . . . . 0 ?
C29 C15 C20 C19 . . . . 177.5(11) ?
O4 C2 C3 C4 . . . . -178.4(10) ?
C7 C2 C3 C4 . . . . 0 ?
C2 C3 C4 C5 . . . . 0 ?
C3 C4 C5 C6 . . . . 0 ?
C3 C4 C5 C34 . . . . 176.7(12) ?
C4 C5 C6 C7 . . . . 0 ?
C34 C5 C6 C7 . . . . -176.8(12) ?
C5 C6 C7 C2 . . . . 0 ?
O4 C2 C7 C6 . . . . 178.3(11) ?
C3 C2 C7 C6 . . . . 0 ?
C13 C8 C9 C10 . . . . 0 ?
C34 C8 C9 C10 . . . . 172.1(11) ?
C8 C9 C10 C11 . . . . 0 ?
C9 C10 C11 O1 . . . . -178.4(13) ?
C9 C10 C11 C12 . . . . 0 ?
O1 C11 C12 C13 . . . . 178.5(12) ?
C10 C11 C12 C13 . . . . 0 ?
C11 C12 C13 C8 . . . . 0 ?
C9 C8 C13 C12 . . . . 0 ?
C34 C8 C13 C12 . . . . -172.3(12) ?
C23 C22 C29 C30 . . . . -30.(2) ?
C27 C22 C29 C30 . . . . 147.7(15) ?
C23 C22 C29 C15 . . . . 151.4(11) ?
C27 C22 C29 C15 . . . . -31.1(19) ?
C16 C15 C29 C30 . . . . 141.0(15) ?
C20 C15 C29 C30 . . . . -36.(2) ?
C16 C15 C29 C22 . . . . -40.1(19) ?
C20 C15 C29 C22 . . . . 142.5(12) ?
C9 C8 C34 C33 . . . . -147.5(14) ?
C13 C8 C34 C33 . . . . 25.(2) ?
C9 C8 C34 C5 . . . . 32.(2) ?
C13 C8 C34 C5 . . . . -155.5(12) ?
C4 C5 C34 C33 . . . . -146.3(14) ?
C6 C5 C34 C33 . . . . 30.(2) ?
C4 C5 C34 C8 . . . . 34.(2) ?
C6 C5 C34 C8 . . . . -149.3(12) ?
C10 C11 O1 C14 . . . . 6.(2) ?
C12 C11 O1 C14 . . . . -172.7(13) ?
C17 C18 O2 C21 . . . . -171.8(11) ?
C19 C18 O2 C21 . . . . 10.9(18) ?
C26 C25 O3 C28 . . . . -175.4(13) ?
C24 C25 O3 C28 . . . . 6.2(19) ?
C3 C2 O4 C1 . . . . 178.1(11) ?
C7 C2 O4 C1 . . . . -0.3(17) ?

