# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2430471'
loop_
_audit_author_name
_audit_author_address
'Alireza Abbasi'
;University of Tehran
Iran
;
_audit_update_record             
;
2025-03-11 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;

;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6698(11)
_cell_length_b                   10.893(2)
_cell_length_c                   13.585(3)
_cell_angle_alpha                72.75(3)
_cell_angle_beta                 85.55(3)
_cell_angle_gamma                86.34(3)
_cell_volume                     798.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4677
_cell_measurement_temperature    290
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.21562
_exptl_absorpt_correction_T_min  0.86684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4747
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.850
_diffrn_ambient_temperature      290
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2057
_reflns_number_total             2478
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1023P)²+0.4574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2176
_refine_ls_wR_factor_ref         0.2259
_refine_special_details          ?
_refinement_description          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C18(H18), C19(H19), C11(H11), C20(H20), C17(H17), C9(H9),
 C6(H6), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O -0.0324(4) 0.7098(2) 0.51948(18) 0.0626(7) Uani 1 1 d . . . . .
O4 O 0.1848(5) 0.5255(2) 0.57408(19) 0.0688(8) Uani 1 1 d . . . . .
O1 O 0.7766(4) 0.9448(2) 0.09601(18) 0.0595(7) Uani 1 1 d . . . . .
O2 O 0.6086(5) 0.8446(3) 0.00324(19) 0.0757(8) Uani 1 1 d . . . . .
C10 C 0.2835(6) 0.7942(3) 0.3526(2) 0.0519(8) Uani 1 1 d . . . . .
H10 H 0.147025 0.843440 0.360409 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5513(6) 0.5383(3) 0.1983(3) 0.0531(8) Uani 1 1 d . . . . .
H16 H 0.639099 0.581792 0.231363 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4974(6) 0.3496(3) 0.1476(3) 0.0603(9) Uani 1 1 d . . . . .
H18 H 0.546788 0.266917 0.146408 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3474(5) 0.5970(3) 0.1521(2) 0.0475(7) Uani 1 1 d . . . . .
C19 C 0.2959(7) 0.4067(4) 0.1012(3) 0.0632(9) Uani 1 1 d . . . . .
H19 H 0.209192 0.363084 0.067860 0.076 Uiso 1 1 calc R U . . .
C2 C 0.4375(6) 0.8153(3) 0.1727(2) 0.0514(8) Uani 1 1 d . . . . .
C11 C 0.3167(6) 0.6842(3) 0.4221(2) 0.0561(8) Uani 1 1 d . . . . .
H11 H 0.453548 0.635468 0.414063 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2560(6) 0.7301(3) 0.1551(3) 0.0568(8) Uani 1 1 d . . . . .
H14A H 0.185875 0.773465 0.090310 0.068 Uiso 1 1 calc R U . . .
H14B H 0.131096 0.720140 0.209562 0.068 Uiso 1 1 calc R U . . .
C1 C 0.6048(7) 0.8667(3) 0.0849(3) 0.0577(9) Uani 1 1 d . . . . .
C12 C 0.1529(6) 0.6305(3) 0.5133(2) 0.0531(8) Uani 1 1 d . . . . .
C20 C 0.2207(6) 0.5296(3) 0.1039(3) 0.0588(9) Uani 1 1 d . . . . .
H20 H 0.082856 0.567192 0.072687 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4495(6) 0.8466(3) 0.2614(2) 0.0502(8) Uani 1 1 d . . . . .
C4 C 0.6246(6) 0.9355(3) 0.2690(2) 0.0518(8) Uani 1 1 d . . . . .
C17 C 0.6260(6) 0.4152(3) 0.1958(3) 0.0584(9) Uani 1 1 d . . . . .
H17 H 0.763634 0.377079 0.226818 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7837(6) 0.9815(3) 0.1838(3) 0.0540(8) Uani 1 1 d . . . . .
C9 C 0.6471(7) 0.9777(3) 0.3557(3) 0.0626(9) Uani 1 1 d . . . . .
H9 H 0.545439 0.947939 0.413966 0.075 Uiso 1 1 calc R U . . .
C6 C 0.9590(6) 1.0654(3) 0.1848(3) 0.0619(9) Uani 1 1 d . . . . .
H6 H 1.063793 1.094347 0.127486 0.074 Uiso 1 1 calc R U . . .
C13 C -0.2103(7) 0.6610(4) 0.6021(3) 0.0703(10) Uani 1 1 d . . . . .
H13A H -0.291450 0.593839 0.588196 0.105 Uiso 1 1 calc R U . . .
H13B H -0.321866 0.729492 0.606707 0.105 Uiso 1 1 calc R U . . .
H13C H -0.135454 0.627396 0.666270 0.105 Uiso 1 1 calc R U . . .
C8 C 0.8162(7) 1.0619(3) 0.3561(3) 0.0683(10) Uani 1 1 d . . . . .
H8 H 0.825190 1.090681 0.413642 0.082 Uiso 1 1 calc R U . . .
C7 C 0.9754(7) 1.1047(3) 0.2703(3) 0.0709(11) Uani 1 1 d . . . . .
H7 H 1.092574 1.159986 0.271671 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C12 1.330(4) . ?
O3 C13 1.449(4) . ?
O4 C12 1.208(4) . ?
O1 C1 1.378(4) . ?
O1 C5 1.370(4) . ?
O2 C1 1.202(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.301(4) . ?
C10 C3 1.488(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.386(5) . ?
C16 C17 1.390(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(5) . ?
C18 C17 1.375(5) . ?
C15 C14 1.519(5) . ?
C15 C20 1.382(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(5) . ?
C2 C14 1.507(5) . ?
C2 C1 1.460(5) . ?
C2 C3 1.354(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.483(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C20 H20 0.9300 . ?
C3 C4 1.460(5) . ?
C4 C5 1.399(5) . ?
C4 C9 1.402(5) . ?
C17 H17 0.9300 . ?
C5 C6 1.395(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.370(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C7 1.400(6) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 C13 116.2(3) . . ?
C5 O1 C1 121.8(3) . . ?
C11 C10 H10 117.8 . . ?
C11 C10 C3 124.3(3) . . ?
C3 C10 H10 117.8 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C19 C18 H18 120.2 . . ?
C19 C18 C17 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C16 C15 C14 122.5(3) . . ?
C20 C15 C16 118.2(3) . . ?
C20 C15 C14 119.3(3) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C1 C2 C14 115.2(3) . . ?
C3 C2 C14 124.5(3) . . ?
C3 C2 C1 120.3(3) . . ?
C10 C11 H11 117.5 . . ?
C10 C11 C12 125.0(3) . . ?
C12 C11 H11 117.5 . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C2 C14 C15 115.8(3) . . ?
C2 C14 H14A 108.3 . . ?
C2 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O1 C1 C2 118.3(3) . . ?
O2 C1 O1 116.5(3) . . ?
O2 C1 C2 125.2(3) . . ?
O3 C12 C11 112.6(3) . . ?
O4 C12 O3 124.2(3) . . ?
O4 C12 C11 123.1(3) . . ?
C15 C20 C19 121.0(3) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C2 C3 C10 121.5(3) . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 C10 118.2(3) . . ?
C5 C4 C3 117.7(3) . . ?
C5 C4 C9 117.2(3) . . ?
C9 C4 C3 125.0(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
O1 C5 C4 121.4(3) . . ?
O1 C5 C6 116.9(3) . . ?
C6 C5 C4 121.6(3) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C6 C7 C8 120.2(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?

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
O1 C5 C6 C7 -179.7(3) . . . . ?
C10 C11 C12 O3 -2.3(5) . . . . ?
C10 C11 C12 O4 176.9(4) . . . . ?
C10 C3 C4 C5 178.4(3) . . . . ?
C10 C3 C4 C9 -1.1(5) . . . . ?
C16 C15 C14 C2 23.0(4) . . . . ?
C16 C15 C20 C19 -0.3(5) . . . . ?
C18 C19 C20 C15 0.6(5) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C19 C18 C17 C16 0.5(5) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
C2 C3 C4 C9 177.7(3) . . . . ?
C11 C10 C3 C2 86.0(4) . . . . ?
C11 C10 C3 C4 -95.2(4) . . . . ?
C14 C15 C20 C19 -178.7(3) . . . . ?
C14 C2 C1 O1 -179.6(3) . . . . ?
C14 C2 C1 O2 -1.1(5) . . . . ?
C14 C2 C3 C10 2.0(5) . . . . ?
C14 C2 C3 C4 -176.8(3) . . . . ?
C1 O1 C5 C4 3.7(4) . . . . ?
C1 O1 C5 C6 -177.2(3) . . . . ?
C1 C2 C14 C15 73.1(4) . . . . ?
C1 C2 C3 C10 -179.1(3) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C20 C15 C14 C2 -158.7(3) . . . . ?
C3 C10 C11 C12 -179.9(3) . . . . ?
C3 C2 C14 C15 -108.0(4) . . . . ?
C3 C2 C1 O1 1.4(4) . . . . ?
C3 C2 C1 O2 179.9(3) . . . . ?
C3 C4 C5 O1 0.0(4) . . . . ?
C3 C4 C5 C6 -179.1(3) . . . . ?
C3 C4 C9 C8 -179.7(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C4 C9 C8 C7 -1.9(6) . . . . ?
C17 C16 C15 C14 178.5(3) . . . . ?
C17 C16 C15 C20 0.2(5) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C5 O1 C1 O2 177.0(3) . . . . ?
C5 O1 C1 C2 -4.3(4) . . . . ?
C5 C4 C9 C8 0.8(5) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C9 C4 C5 O1 179.5(3) . . . . ?
C9 C4 C5 C6 0.4(5) . . . . ?
C9 C8 C7 C6 1.7(6) . . . . ?
C13 O3 C12 O4 -3.4(5) . . . . ?
C13 O3 C12 C11 175.7(3) . . . . ?

# start Validation Reply Form
_vrf_PLAT029_1                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.883 Why?  
RESPONSE: Due to geometrical limitations of the goniometer (one-circle), 
we were not able to cover full data set.
;
# end Validation Reply Form

_submission_special_instructions 'No special instructions were received'
