# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_wzf-20230712_auto
_database_code_depnum_ccdc_archive 'CCDC 2294355'
loop_
_audit_author_name
_audit_author_address
'Zhaofeng Wang HSS'
;Hunan University
China
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 O4'
_chemical_formula_weight         372.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.57076(8)
_cell_length_b                   7.79768(12)
_cell_length_c                   42.0452(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1826.40(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    7349
_cell_measurement_theta_min      2.1050
_cell_measurement_theta_max      76.1640

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.742
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9451
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         76.348
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3628
_reflns_number_gt                3456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0384P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1325 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3628
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
O8 O -1.0131(2) -0.87192(17) -0.63437(3) 0.0268(3) Uani 1 1 d . . . . .
O11 O -1.2229(2) -0.63168(16) -0.62131(3) 0.0268(3) Uani 1 1 d . . . . .
O21 O -0.8932(3) -0.35504(18) -0.67205(4) 0.0375(4) Uani 1 1 d . . . . .
O18 O -0.1962(3) -0.93871(19) -0.73646(4) 0.0332(3) Uani 1 1 d . . . . .
C23 C -1.2646(3) -1.0239(2) -0.48637(4) 0.0201(4) Uani 1 1 d . . . . .
C4 C -1.2596(3) -0.9684(2) -0.52039(4) 0.0202(4) Uani 1 1 d . . . . .
C1 C -1.2394(3) -0.8695(2) -0.58487(4) 0.0224(4) Uani 1 1 d . . . . .
C26 C -1.2692(3) -1.1334(2) -0.42244(4) 0.0254(4) Uani 1 1 d . . . . .
H26 H -1.270917 -1.170422 -0.400920 0.030 Uiso 1 1 calc R U . . .
C7 C -1.2302(4) -0.8145(2) -0.61904(5) 0.0251(4) Uani 1 1 d . . . . .
H7 H -1.373416 -0.859685 -0.630687 0.030 Uiso 1 1 calc R U . . .
C24 C -1.0823(3) -0.9786(2) -0.46517(5) 0.0260(4) Uani 1 1 d . . . . .
H24 H -0.953626 -0.909096 -0.472485 0.031 Uiso 1 1 calc R U . . .
C9 C -0.9276(3) -0.7366(2) -0.65228(4) 0.0227(4) Uani 1 1 d . . . . .
C2 C -1.0597(4) -0.8206(2) -0.56389(5) 0.0276(4) Uani 1 1 d . . . . .
H2 H -0.929170 -0.753014 -0.571270 0.033 Uiso 1 1 calc R U . . .
C10 C -1.0521(3) -0.5932(2) -0.64463(4) 0.0228(4) Uani 1 1 d . . . . .
C5 C -1.4396(3) -1.0146(3) -0.54169(4) 0.0258(4) Uani 1 1 d . . . . .
H5 H -1.571610 -1.080669 -0.534332 0.031 Uiso 1 1 calc R U . . .
C12 C -0.7365(3) -0.7813(2) -0.67448(4) 0.0226(4) Uani 1 1 d . . . . .
C27 C -1.4526(4) -1.1799(3) -0.44300(4) 0.0283(4) Uani 1 1 d . . . . .
H27 H -1.580601 -1.249520 -0.435507 0.034 Uiso 1 1 calc R U . . .
C3 C -1.0693(4) -0.8695(3) -0.53231(5) 0.0266(4) Uani 1 1 d . . . . .
H3 H -0.944089 -0.835418 -0.518343 0.032 Uiso 1 1 calc R U . . .
C6 C -1.4304(3) -0.9660(2) -0.57358(5) 0.0259(4) Uani 1 1 d . . . . .
H6 H -1.555541 -0.999106 -0.587646 0.031 Uiso 1 1 calc R U . . .
C28 C -1.4507(3) -1.1255(3) -0.47444(4) 0.0258(4) Uani 1 1 d . . . . .
H28 H -1.578520 -1.158035 -0.488126 0.031 Uiso 1 1 calc R U . . .
C25 C -1.0840(3) -1.0325(2) -0.43367(5) 0.0282(4) Uani 1 1 d . . . . .
H25 H -0.957295 -0.999762 -0.419814 0.034 Uiso 1 1 calc R U . . .
C17 C -0.5965(3) -0.6585(2) -0.68995(4) 0.0260(4) Uani 1 1 d . . . . .
H17 H -0.626304 -0.540293 -0.686196 0.031 Uiso 1 1 calc R U . . .
C20 C -1.0492(4) -0.4139(2) -0.65458(4) 0.0251(4) Uani 1 1 d . . . . .
C16 C -0.4144(4) -0.7060(3) -0.71073(5) 0.0280(4) Uani 1 1 d . . . . .
H16 H -0.320151 -0.620675 -0.720936 0.034 Uiso 1 1 calc R U . . .
C15 C -0.3702(4) -0.8790(3) -0.71659(4) 0.0268(4) Uani 1 1 d . . . . .
C14 C -0.5100(4) -1.0025(3) -0.70152(4) 0.0280(4) Uani 1 1 d . . . . .
H14 H -0.480676 -1.120532 -0.705576 0.034 Uiso 1 1 calc R U . . .
C13 C -0.6908(4) -0.9560(2) -0.68074(4) 0.0259(4) Uani 1 1 d . . . . .
H13 H -0.784589 -1.041904 -0.670643 0.031 Uiso 1 1 calc R U . . .
C19 C -0.0434(4) -0.8150(3) -0.75115(5) 0.0341(5) Uani 1 1 d . . . . .
H19A H 0.075718 -0.873783 -0.764383 0.051 Uiso 1 1 calc R U . . .
H19B H 0.038831 -0.748069 -0.734697 0.051 Uiso 1 1 calc R U . . .
H19C H -0.139835 -0.738114 -0.764445 0.051 Uiso 1 1 calc R U . . .
C22 C -1.2469(4) -0.3023(2) -0.64186(5) 0.0287(4) Uani 1 1 d . . . . .
H22A H -1.238919 -0.299953 -0.618584 0.043 Uiso 1 1 calc R U . . .
H22B H -1.402452 -0.348535 -0.648552 0.043 Uiso 1 1 calc R U . . .
H22C H -1.228190 -0.185605 -0.650159 0.043 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
O8 C9 1.381(2) . ?
O8 C7 1.442(2) . ?
O11 C10 1.399(2) . ?
O11 C7 1.430(2) . ?
O21 C20 1.227(2) . ?
O18 C15 1.362(2) . ?
O18 C19 1.427(3) . ?
C23 C24 1.397(3) . ?
C23 C28 1.398(3) . ?
C23 C4 1.495(2) . ?
C4 C5 1.392(3) . ?
C4 C3 1.403(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.388(3) . ?
C1 C7 1.500(3) . ?
C26 C25 1.381(3) . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C7 H7 1.0000 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C9 C10 1.354(3) . ?
C9 C12 1.458(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C10 C20 1.460(2) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C12 C17 1.396(3) . ?
C12 C13 1.411(3) . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C28 H28 0.9500 . ?
C25 H25 0.9500 . ?
C17 C16 1.389(3) . ?
C17 H17 0.9500 . ?
C20 C22 1.502(3) . ?
C16 C15 1.393(3) . ?
C16 H16 0.9500 . ?
C15 C14 1.391(3) . ?
C14 C13 1.382(3) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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 O8 C7 107.22(14) . . ?
C10 O11 C7 106.26(14) . . ?
C15 O18 C19 117.32(16) . . ?
C24 C23 C28 116.96(16) . . ?
C24 C23 C4 121.60(16) . . ?
C28 C23 C4 121.43(16) . . ?
C5 C4 C3 117.16(17) . . ?
C5 C4 C23 121.82(15) . . ?
C3 C4 C23 121.01(16) . . ?
C6 C1 C2 119.02(16) . . ?
C6 C1 C7 120.58(17) . . ?
C2 C1 C7 120.38(17) . . ?
C25 C26 C27 119.12(17) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
O11 C7 O8 104.82(14) . . ?
O11 C7 C1 110.47(15) . . ?
O8 C7 C1 111.59(15) . . ?
O11 C7 H7 110.0 . . ?
O8 C7 H7 110.0 . . ?
C1 C7 H7 110.0 . . ?
C25 C24 C23 121.81(17) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C10 C9 O8 108.93(15) . . ?
C10 C9 C12 136.33(17) . . ?
O8 C9 C12 114.72(15) . . ?
C3 C2 C1 120.43(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C9 C10 O11 109.75(15) . . ?
C9 C10 C20 135.81(18) . . ?
O11 C10 C20 114.43(16) . . ?
C4 C5 C6 121.47(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C17 C12 C13 118.31(17) . . ?
C17 C12 C9 122.85(17) . . ?
C13 C12 C9 118.84(16) . . ?
C26 C27 C28 120.53(18) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C2 C3 C4 121.62(18) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C1 C6 C5 120.30(17) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C27 C28 C23 121.36(18) . . ?
C27 C28 H28 119.3 . . ?
C23 C28 H28 119.3 . . ?
C26 C25 C24 120.21(18) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C16 C17 C12 121.24(18) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
O21 C20 C10 122.52(18) . . ?
O21 C20 C22 121.06(17) . . ?
C10 C20 C22 116.41(17) . . ?
C17 C16 C15 119.88(18) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O18 C15 C14 116.17(18) . . ?
O18 C15 C16 124.41(18) . . ?
C14 C15 C16 119.42(18) . . ?
C13 C14 C15 120.93(18) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C13 C12 120.23(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C24 C23 C4 C5 179.34(18) . . . . ?
C28 C23 C4 C5 0.2(3) . . . . ?
C24 C23 C4 C3 0.5(3) . . . . ?
C28 C23 C4 C3 -178.57(18) . . . . ?
C10 O11 C7 O8 16.67(18) . . . . ?
C10 O11 C7 C1 137.00(15) . . . . ?
C9 O8 C7 O11 -16.82(18) . . . . ?
C9 O8 C7 C1 -136.40(15) . . . . ?
C6 C1 C7 O11 120.38(19) . . . . ?
C2 C1 C7 O11 -57.9(2) . . . . ?
C6 C1 C7 O8 -123.44(18) . . . . ?
C2 C1 C7 O8 58.3(2) . . . . ?
C28 C23 C24 C25 0.3(3) . . . . ?
C4 C23 C24 C25 -178.81(17) . . . . ?
C7 O8 C9 C10 10.6(2) . . . . ?
C7 O8 C9 C12 -168.12(15) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C1 C2 C3 179.27(17) . . . . ?
O8 C9 C10 O11 0.1(2) . . . . ?
C12 C9 C10 O11 178.46(19) . . . . ?
O8 C9 C10 C20 179.8(2) . . . . ?
C12 C9 C10 C20 -1.9(4) . . . . ?
C7 O11 C10 C9 -10.9(2) . . . . ?
C7 O11 C10 C20 169.40(16) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C23 C4 C5 C6 -178.33(17) . . . . ?
C10 C9 C12 C17 14.6(3) . . . . ?
O8 C9 C12 C17 -167.18(17) . . . . ?
C10 C9 C12 C13 -165.3(2) . . . . ?
O8 C9 C12 C13 13.0(2) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C23 C4 C3 C2 178.53(17) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C7 C1 C6 C5 -179.08(17) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C26 C27 C28 C23 0.4(3) . . . . ?
C24 C23 C28 C27 -0.5(3) . . . . ?
C4 C23 C28 C27 178.65(17) . . . . ?
C27 C26 C25 C24 0.0(3) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
C9 C12 C17 C16 179.39(17) . . . . ?
C9 C10 C20 O21 -8.1(4) . . . . ?
O11 C10 C20 O21 171.50(17) . . . . ?
C9 C10 C20 C22 172.8(2) . . . . ?
O11 C10 C20 C22 -7.6(2) . . . . ?
C12 C17 C16 C15 0.5(3) . . . . ?
C19 O18 C15 C14 -177.32(17) . . . . ?
C19 O18 C15 C16 2.7(3) . . . . ?
C17 C16 C15 O18 -179.90(17) . . . . ?
C17 C16 C15 C14 0.1(3) . . . . ?
O18 C15 C14 C13 179.67(17) . . . . ?
C16 C15 C14 C13 -0.3(3) . . . . ?
C15 C14 C13 C12 0.0(3) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C9 C12 C13 C14 -179.61(17) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035



