# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_EXP13-2
_database_code_depnum_ccdc_archive 'CCDC 1856407'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2018-07-17 deposited with the CCDC.	2020-09-30 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C39 H40 O4'
_chemical_formula_moiety         'C39 H40 O4'
_chemical_formula_weight         572.74
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
_space_group_IT_number           36
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,+Z
3 -X,-Y,1/2+Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,+Z
7 1/2-X,1/2-Y,1/2+Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   72.700(3)
_cell_length_b                   7.1925(3)
_cell_length_c                   6.0961(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3187.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12043
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224.00
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  0.887

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

_diffrn_ambient_temperature      123
_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            17743
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         3.648
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_limit_h_min       -87
_diffrn_reflns_limit_h_max       86
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2894
_reflns_number_gt                2475
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.964

#==============================================================================
# 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          0.0548
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0897
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2894
_refine_ls_number_parameters     197
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0412P)²+0.0802P] 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_diff_density_max         0.22
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.78(13)

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 0.22832(2) 0.2400(2) 1.1983(3) 0.0315(5) Uani 1 1 d . . . . .
O2 O 0.07306(2) 0.2603(2) 0.3635(3) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.23250(3) 0.3387(4) 1.3945(5) 0.0380(7) Uani 1 1 d . . . . .
H1A H 0.2300 0.4714 1.3729 0.046 Uiso 1 1 calc R U . . .
H1B H 0.2455 0.3210 1.4313 0.046 Uiso 1 1 calc R U . . .
H1C H 0.2248 0.2916 1.5145 0.046 Uiso 1 1 calc R U . . .
C2 C 0.21061(3) 0.2471(3) 1.1220(4) 0.0265(6) Uani 1 1 d . . . . .
C3 C 0.20760(3) 0.1600(3) 0.9233(4) 0.0279(6) Uani 1 1 d . . . . .
H3 H 0.2175 0.1009 0.8496 0.033 Uiso 1 1 calc R U . . .
C4 C 0.19025(3) 0.1583(3) 0.8310(4) 0.0293(6) Uani 1 1 d . . . . .
H4 H 0.1884 0.0984 0.6939 0.035 Uiso 1 1 calc R U . . .
C5 C 0.17540(3) 0.2442(3) 0.9374(4) 0.0263(6) Uani 1 1 d . . . . .
C6 C 0.17863(3) 0.3294(3) 1.1386(4) 0.0292(6) Uani 1 1 d . . . . .
H6 H 0.1687 0.3866 1.2143 0.035 Uiso 1 1 calc R U . . .
C7 C 0.19611(3) 0.3325(3) 1.2310(4) 0.0283(6) Uani 1 1 d . . . . .
H7 H 0.1981 0.3925 1.3677 0.034 Uiso 1 1 calc R U . . .
C8 C 0.15761(4) 0.2480(3) 0.8358(5) 0.0300(6) Uani 1 1 d . . . . .
C9 C 0.14309(4) 0.2546(3) 0.7440(4) 0.0297(6) Uani 1 1 d . . . . .
C10 C 0.12536(3) 0.2560(3) 0.6409(5) 0.0280(6) Uani 1 1 d . . . . .
C11 C 0.12250(3) 0.1689(3) 0.4393(4) 0.0288(6) Uani 1 1 d . . . . .
H11 H 0.1326 0.1119 0.3667 0.035 Uiso 1 1 calc R U . . .
C12 C 0.10526(3) 0.1635(3) 0.3427(4) 0.0281(6) Uani 1 1 d . . . . .
H12 H 0.1035 0.1007 0.2072 0.034 Uiso 1 1 calc R U . . .
C13 C 0.09060(3) 0.2511(3) 0.4459(4) 0.0255(6) Uani 1 1 d . . . . .
C14 C 0.09319(3) 0.3400(3) 0.6461(4) 0.0279(6) Uani 1 1 d . . . . .
H14 H 0.0831 0.3993 0.7165 0.033 Uiso 1 1 calc R U . . .
C15 C 0.11038(3) 0.3421(3) 0.7428(5) 0.0286(6) Uani 1 1 d . . . . .
H15 H 0.1120 0.4028 0.8798 0.034 Uiso 1 1 calc R U . . .
C16 C 0.06999(3) 0.1870(4) 0.1476(5) 0.0337(7) Uani 1 1 d . . . . .
H16A H 0.0694 0.0496 0.1533 0.040 Uiso 1 1 calc R U . . .
H16B H 0.0802 0.2227 0.0494 0.040 Uiso 1 1 calc R U . . .
C17 C 0.05215(3) 0.2645(3) 0.0618(5) 0.0366(7) Uani 1 1 d . . . . .
H17A H 0.0508 0.2274 -0.0937 0.044 Uiso 1 1 calc R U . . .
H17B H 0.0528 0.4020 0.0666 0.044 Uiso 1 1 calc R U . . .
C18 C 0.03508(3) 0.2020(4) 0.1870(5) 0.0387(7) Uani 1 1 d . . . . .
H18A H 0.0345 0.0645 0.1863 0.046 Uiso 1 1 calc R U . . .
H18B H 0.0361 0.2432 0.3415 0.046 Uiso 1 1 calc R U . . .
C19 C 0.01748(3) 0.2793(3) 0.0886(5) 0.0420(8) Uani 1 1 d . . . . .
H19A H 0.0170 0.2453 -0.0686 0.050 Uiso 1 1 calc R U . . .
H19B H 0.0178 0.4167 0.0980 0.050 Uiso 1 1 calc R U . . .
C20 C 0.0000 0.2092(5) 0.2013(8) 0.0439(11) Uani 1 2 d S T P . .
H20A H 0.0000 0.0716 0.2007 0.053 Uiso 1 2 calc R U P . .
H20B H 0.0000 0.2510 0.3560 0.053 Uiso 1 2 calc R U P . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# 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 C2 1.370(3) . ?
O1 C1 1.424(3) . ?
O2 C13 1.372(3) . ?
O2 C16 1.435(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.381(3) . ?
C2 C7 1.389(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 C8 1.435(3) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.195(3) . ?
C9 C10 1.435(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.398(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.506(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.518(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.530(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C19 1.530(3) 2 ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C2 O1 C1 117.84(19) . . ?
C13 O2 C16 117.55(19) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 115.5(2) . . ?
O1 C2 C7 124.6(2) . . ?
C3 C2 C7 119.9(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 C8 121.6(2) . . ?
C4 C5 C8 120.2(2) . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C2 C7 C6 119.6(2) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C5 177.4(3) . . ?
C8 C9 C10 177.3(3) . . ?
C11 C10 C15 118.3(2) . . ?
C11 C10 C9 121.1(2) . . ?
C15 C10 C9 120.5(3) . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
O2 C13 C12 124.7(2) . . ?
O2 C13 C14 115.2(2) . . ?
C12 C13 C14 120.1(2) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O2 C16 C17 108.5(2) . . ?
O2 C16 H16A 110.0 . . ?
C17 C16 H16A 110.0 . . ?
O2 C16 H16B 110.0 . . ?
C17 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C16 C17 C18 114.7(2) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 112.3(2) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 113.7(3) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C19 112.3(4) 2 . ?
C19 C20 H20A 109.1 2 . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 2 . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 C3 175.6(2) . . . . ?
C1 O1 C2 C7 -5.0(3) . . . . ?
O1 C2 C3 C4 179.9(2) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 C8 177.5(2) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C8 C5 C6 C7 -177.0(2) . . . . ?
O1 C2 C7 C6 -179.4(2) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
C5 C6 C7 C2 -0.7(4) . . . . ?
C15 C10 C11 C12 -1.3(3) . . . . ?
C9 C10 C11 C12 177.5(2) . . . . ?
C10 C11 C12 C13 1.7(4) . . . . ?
C16 O2 C13 C12 -5.1(3) . . . . ?
C16 O2 C13 C14 174.0(2) . . . . ?
C11 C12 C13 O2 177.9(2) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
O2 C13 C14 C15 -179.0(2) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C9 C10 C15 C14 -178.5(2) . . . . ?
C13 O2 C16 C17 -161.9(2) . . . . ?
O2 C16 C17 C18 -65.6(3) . . . . ?
C16 C17 C18 C19 -178.1(2) . . . . ?
C17 C18 C19 C20 176.3(3) . . . . ?
C18 C19 C20 C19 -176.1(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.


