# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2250166'
loop_
_audit_author_name
_audit_author_address
'Catherine Raptopoulou'
;NCSR Demokritos
Greece
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 O5'
_chemical_formula_weight         344.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.1705(9)
_cell_length_b                   16.4186(10)
_cell_length_c                   17.4433(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3485.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    11842
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.46

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'RIGAKU R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18828
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3801
_reflns_number_gt                2466
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear, Rigaku MSC, 2005'
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond ver.3.2'
_computing_publication_material  'publCIF J.Appl.Cryst. 2010, 43, 920'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0898P)²+1.6671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3801
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70700(13) 0.06997(10) 0.57127(9) 0.0265(4) Uani 1 1 d . . . . .
O2 O 0.65690(13) 0.19270(10) 0.40740(9) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.60401(15) 0.10916(11) 0.31230(10) 0.0369(5) Uani 1 1 d . . . . .
O4 O 0.58677(16) -0.07775(12) 0.40985(13) 0.0498(6) Uani 1 1 d . . . . .
O5 O 1.05961(13) 0.03115(11) 0.42725(10) 0.0298(4) Uani 1 1 d . . . . .
C1 C 0.81632(18) 0.21456(14) 0.48880(13) 0.0222(5) Uani 1 1 d . . . . .
C2 C 0.84895(19) 0.24747(14) 0.56624(13) 0.0233(5) Uani 1 1 d . . . . .
C3 C 0.78164(18) 0.26702(14) 0.62333(13) 0.0238(5) Uani 1 1 d . . . . .
C4 C 0.65806(19) 0.26293(15) 0.61595(14) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.62060(19) 0.24242(15) 0.53367(13) 0.0246(5) Uani 1 1 d . . . . .
C6 C 0.69386(18) 0.18610(14) 0.48671(12) 0.0222(5) Uani 1 1 d . . . . .
C7 C 0.68357(17) 0.09532(14) 0.50094(13) 0.0222(5) Uani 1 1 d . . . . .
C8 C 0.65683(18) 0.05515(15) 0.43613(13) 0.0246(5) Uani 1 1 d . . . . .
C9 C 0.63527(19) 0.11709(15) 0.37777(14) 0.0271(5) Uani 1 1 d . . . . .
C10 C 0.6654(2) -0.03348(15) 0.41388(14) 0.0278(5) Uani 1 1 d . . . . .
C11 C 0.7817(2) -0.06122(16) 0.39490(15) 0.0295(6) Uani 1 1 d . . . . .
C12 C 0.8250(2) -0.02212(16) 0.31999(14) 0.0283(5) Uani 1 1 d . . . . .
C13 C 0.9506(2) -0.00783(15) 0.31863(14) 0.0271(5) Uani 1 1 d . . . . .
C14 C 0.98424(18) 0.04806(14) 0.38373(13) 0.0236(5) Uani 1 1 d . . . . .
C15 C 0.91886(18) 0.12399(14) 0.39535(14) 0.0233(5) Uani 1 1 d . . . . .
C16 C 0.89231(18) 0.14576(14) 0.46580(13) 0.0223(5) Uani 1 1 d . . . . .
C17 C 0.8255(2) 0.29509(19) 0.69982(16) 0.0344(6) Uani 1 1 d . . . . .
C18 C 0.6051(2) 0.20989(17) 0.67749(15) 0.0319(6) Uani 1 1 d . . . . .
C19 C 0.6827(3) -0.01436(16) 0.58965(16) 0.0324(6) Uani 1 1 d . . . . .
C20 C 1.0182(3) -0.0854(2) 0.31760(19) 0.0432(7) Uani 1 1 d . . . . .
H1 H 0.8233(19) 0.2573(15) 0.4522(14) 0.019(6) Uiso 1 1 d . . . . .
H2 H 0.929(2) 0.2534(15) 0.5749(14) 0.023(6) Uiso 1 1 d . . . . .
H4 H 0.630(2) 0.3188(18) 0.6271(16) 0.038(7) Uiso 1 1 d . . . . .
H5A H 0.616(2) 0.2946(15) 0.5025(14) 0.023(6) Uiso 1 1 d . . . . .
H5B H 0.544(2) 0.2213(15) 0.5313(13) 0.022(6) Uiso 1 1 d . . . . .
H11A H 0.780(2) -0.1229(19) 0.3915(15) 0.041(8) Uiso 1 1 d . . . . .
H11B H 0.830(2) -0.0453(16) 0.4369(15) 0.028(7) Uiso 1 1 d . . . . .
H12A H 0.784(2) 0.0316(17) 0.3125(14) 0.028(7) Uiso 1 1 d . . . . .
H12B H 0.801(2) -0.0556(19) 0.2748(18) 0.047(8) Uiso 1 1 d . . . . .
H13 H 0.964(2) 0.0236(16) 0.2707(16) 0.031(7) Uiso 1 1 d . . . . .
H15 H 0.893(2) 0.1523(17) 0.3490(16) 0.035(7) Uiso 1 1 d . . . . .
H16 H 0.922(2) 0.1125(17) 0.5062(16) 0.034(7) Uiso 1 1 d . . . . .
H17A H 0.783(2) 0.3420(18) 0.7192(16) 0.037(7) Uiso 1 1 d . . . . .
H17B H 0.818(2) 0.2530(19) 0.7381(17) 0.042(8) Uiso 1 1 d . . . . .
H17C H 0.908(3) 0.3069(17) 0.6981(16) 0.041(8) Uiso 1 1 d . . . . .
H18A H 0.633(2) 0.1551(18) 0.6733(16) 0.036(7) Uiso 1 1 d . . . . .
H18B H 0.523(2) 0.2069(17) 0.6688(15) 0.038(8) Uiso 1 1 d . . . . .
H18C H 0.616(2) 0.2319(18) 0.7303(17) 0.040(8) Uiso 1 1 d . . . . .
H19A H 0.729(3) -0.049(2) 0.5611(18) 0.053(10) Uiso 1 1 d . . . . .
H19B H 0.609(3) -0.0242(19) 0.5743(17) 0.047(9) Uiso 1 1 d . . . . .
H19C H 0.696(2) -0.0193(18) 0.6440(19) 0.045(8) Uiso 1 1 d . . . . .
H20A H 1.094(3) -0.0725(19) 0.3235(18) 0.051(9) Uiso 1 1 d . . . . .
H20B H 1.010(3) -0.1118(19) 0.2682(19) 0.055(9) Uiso 1 1 d . . . . .
H20C H 0.994(3) -0.125(2) 0.363(2) 0.062(10) Uiso 1 1 d . . . . .


_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 C7 1.327(3) . ?
O1 C19 1.452(3) . ?
O2 C9 1.370(3) . ?
O2 C6 1.459(3) . ?
O3 C9 1.211(3) . ?
O4 C10 1.204(3) . ?
O5 C14 1.223(3) . ?
C1 C2 1.508(3) . ?
C1 C16 1.514(3) . ?
C1 C6 1.562(3) . ?
C2 C3 1.329(3) . ?
C3 C17 1.509(3) . ?
C3 C4 1.511(3) . ?
C4 C18 1.525(3) . ?
C4 C5 1.543(3) . ?
C5 C6 1.523(3) . ?
C6 C7 1.516(3) . ?
C7 C8 1.349(3) . ?
C8 C9 1.463(3) . ?
C8 C10 1.510(3) . ?
C10 C11 1.523(3) . ?
C11 C12 1.548(4) . ?
C12 C13 1.547(3) . ?
C13 C14 1.516(3) . ?
C13 C20 1.517(4) . ?
C14 C15 1.493(3) . ?
C15 C16 1.320(3) . ?

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
C7 O1 C19 117.36(19) . . ?
C9 O2 C6 110.47(17) . . ?
C2 C1 C16 110.11(19) . . ?
C2 C1 C6 112.29(18) . . ?
C16 C1 C6 110.69(19) . . ?
C3 C2 C1 126.5(2) . . ?
C2 C3 C17 121.2(2) . . ?
C2 C3 C4 122.6(2) . . ?
C17 C3 C4 116.2(2) . . ?
C3 C4 C18 112.7(2) . . ?
C3 C4 C5 112.53(19) . . ?
C18 C4 C5 113.9(2) . . ?
C6 C5 C4 117.36(18) . . ?
O2 C6 C7 101.70(17) . . ?
O2 C6 C5 106.52(17) . . ?
C7 C6 C5 117.41(19) . . ?
O2 C6 C1 107.10(17) . . ?
C7 C6 C1 111.66(18) . . ?
C5 C6 C1 111.36(19) . . ?
O1 C7 C8 132.4(2) . . ?
O1 C7 C6 116.23(19) . . ?
C8 C7 C6 111.3(2) . . ?
C7 C8 C9 106.7(2) . . ?
C7 C8 C10 132.1(2) . . ?
C9 C8 C10 120.2(2) . . ?
O3 C9 O2 120.9(2) . . ?
O3 C9 C8 129.6(2) . . ?
O2 C9 C8 109.4(2) . . ?
O4 C10 C8 122.8(2) . . ?
O4 C10 C11 123.1(2) . . ?
C8 C10 C11 114.1(2) . . ?
C10 C11 C12 112.1(2) . . ?
C13 C12 C11 114.3(2) . . ?
C14 C13 C20 111.8(2) . . ?
C14 C13 C12 110.33(19) . . ?
C20 C13 C12 114.1(2) . . ?
O5 C14 C15 120.3(2) . . ?
O5 C14 C13 122.0(2) . . ?
C15 C14 C13 117.58(19) . . ?
C16 C15 C14 118.9(2) . . ?
C15 C16 C1 126.7(2) . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

