# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ome_auto
_database_code_depnum_ccdc_archive 'CCDC 2426720'
loop_
_audit_author_name
_audit_author_address
ghegw
;Chinese Academy of Sciences Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2025-02-25 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_audit_creation_date             2024-11-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_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 0.0137 0.0067 '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 0.0389 0.0241 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2453(6)
_cell_length_b                   9.2017(3)
_cell_length_c                   21.5805(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.328(3)
_cell_angle_gamma                90
_cell_volume                     1635.98(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11117
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.9270
_cell_measurement_theta_min      3.5620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16570
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         55.035
_diffrn_reflns_theta_min         3.564
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2810
_reflns_number_total             3092
_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       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+0.5988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C2(H2), C16(H16), C3(H3), C6(H6), C14(H14), C17(H17),
 C15(H15)
1.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C20(H20A,H20B,H20C)
1.d :
 C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O21 O 0.17786(10) 0.35209(9) 0.28226(4) 0.0213(2) Uani 1 1 d . . . . .
O11 O 0.13655(9) 0.77475(8) 0.37255(3) 0.01623(19) Uani 1 1 d . . . . .
O19 O 0.09069(10) 0.28544(8) 0.37560(4) 0.0188(2) Uani 1 1 d . . . . .
O24 O 0.49150(10) 0.81916(9) 0.12109(4) 0.0200(2) Uani 1 1 d . . . . .
C13 C -0.21475(14) 0.77755(12) 0.47449(5) 0.0174(2) Uani 1 1 d . . . . .
H13 H -0.163666 0.761373 0.514145 0.021 Uiso 1 1 calc R U . . .
C5 C 0.44649(13) 0.65633(12) 0.20110(5) 0.0176(2) Uani 1 1 d . . . . .
H5 H 0.527576 0.596112 0.184457 0.021 Uiso 1 1 calc R U . . .
C2 C 0.21440(13) 0.83367(12) 0.25070(5) 0.0162(2) Uani 1 1 d . . . . .
H2 H 0.136049 0.895408 0.268204 0.019 Uiso 1 1 calc R U . . .
C16 C -0.36503(14) 0.82309(13) 0.35909(6) 0.0208(3) Uani 1 1 d . . . . .
H16 H -0.416753 0.838134 0.319465 0.025 Uiso 1 1 calc R U . . .
C9 C 0.13407(13) 0.52944(12) 0.36151(5) 0.0155(2) Uani 1 1 d . . . . .
C22 C 0.13658(13) 0.78923(12) 0.48184(5) 0.0175(2) Uani 1 1 d . . . . .
C3 C 0.29043(14) 0.87801(12) 0.19767(5) 0.0174(2) Uani 1 1 d . . . . .
H3 H 0.263163 0.968378 0.178680 0.021 Uiso 1 1 calc R U . . .
C6 C 0.36876(13) 0.61249(12) 0.25310(5) 0.0170(2) Uani 1 1 d . . . . .
H6 H 0.395576 0.521620 0.271725 0.020 Uiso 1 1 calc R U . . .
C14 C -0.37872(14) 0.81187(13) 0.46971(6) 0.0201(3) Uani 1 1 d . . . . .
H14 H -0.439373 0.819340 0.506078 0.024 Uiso 1 1 calc R U . . .
C1 C 0.25052(13) 0.70049(12) 0.27883(5) 0.0151(2) Uani 1 1 d . . . . .
C25 C 0.45269(15) 0.95079(13) 0.08877(6) 0.0230(3) Uani 1 1 d . . . . .
H25A H 0.522400 0.960659 0.053295 0.034 Uiso 1 1 calc R U . . .
H25B H 0.470299 1.033587 0.116803 0.034 Uiso 1 1 calc R U . . .
H25C H 0.338727 0.948496 0.074019 0.034 Uiso 1 1 calc R U . . .
C17 C -0.20070(14) 0.78909(12) 0.36346(5) 0.0181(2) Uani 1 1 d . . . . .
H17 H -0.140461 0.781143 0.327013 0.022 Uiso 1 1 calc R U . . .
C12 C -0.12477(13) 0.76672(12) 0.42146(5) 0.0153(2) Uani 1 1 d . . . . .
C15 C -0.45425(14) 0.83530(13) 0.41193(6) 0.0210(3) Uani 1 1 d . . . . .
H15 H -0.566272 0.859516 0.408611 0.025 Uiso 1 1 calc R U . . .
C8 C 0.07419(14) 0.55466(12) 0.42569(5) 0.0169(2) Uani 1 1 d . . . . .
H8A H 0.154568 0.521304 0.457936 0.020 Uiso 1 1 calc R U . . .
H8B H -0.030365 0.504541 0.431460 0.020 Uiso 1 1 calc R U . . .
C10 C 0.17265(13) 0.65815(12) 0.33603(5) 0.0149(2) Uani 1 1 d . . . . .
C23 C 0.20242(14) 0.84143(13) 0.52637(6) 0.0219(3) Uani 1 1 d . . . . .
H23 H 0.255151 0.883243 0.562045 0.026 Uiso 1 1 calc R U . . .
C7 C 0.05354(13) 0.72233(12) 0.42731(5) 0.0157(2) Uani 1 1 d . . . . .
C18 C 0.13988(13) 0.38419(12) 0.33408(5) 0.0157(2) Uani 1 1 d . . . . .
C4 C 0.40731(13) 0.78832(12) 0.17263(5) 0.0161(2) Uani 1 1 d . . . . .
C20 C 0.08558(16) 0.13676(12) 0.35453(6) 0.0231(3) Uani 1 1 d . . . . .
H20A H -0.001521 0.125477 0.322625 0.035 Uiso 1 1 calc R U . . .
H20B H 0.065069 0.072455 0.389551 0.035 Uiso 1 1 calc R U . . .
H20C H 0.189731 0.111289 0.337078 0.035 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
O21 C18 1.2102(14) . ?
O11 C10 1.3713(13) . ?
O11 C7 1.4707(12) . ?
O19 C18 1.3501(14) . ?
O19 C20 1.4418(13) . ?
O24 C25 1.4275(14) . ?
O24 C4 1.3647(13) . ?
C13 C14 1.3881(17) . ?
C13 C12 1.3926(15) . ?
C5 C6 1.3752(16) . ?
C5 C4 1.3932(16) . ?
C2 C3 1.3883(16) . ?
C2 C1 1.3944(16) . ?
C16 C17 1.3901(17) . ?
C16 C15 1.3866(17) . ?
C9 C8 1.5072(15) . ?
C9 C10 1.3493(16) . ?
C9 C18 1.4634(15) . ?
C22 C23 1.1861(17) . ?
C22 C7 1.4721(16) . ?
C3 C4 1.3944(16) . ?
C6 C1 1.3995(16) . ?
C14 C15 1.3879(17) . ?
C1 C10 1.4670(15) . ?
C17 C12 1.3918(16) . ?
C12 C7 1.5262(15) . ?
C8 C7 1.5527(15) . ?

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
C10 O11 C7 108.91(8) . . ?
C18 O19 C20 115.78(9) . . ?
C4 O24 C25 117.60(9) . . ?
C14 C13 C12 120.33(11) . . ?
C6 C5 C4 120.54(10) . . ?
C3 C2 C1 121.43(10) . . ?
C15 C16 C17 120.70(11) . . ?
C10 C9 C8 109.32(10) . . ?
C10 C9 C18 128.66(10) . . ?
C18 C9 C8 121.99(10) . . ?
C23 C22 C7 178.92(12) . . ?
C2 C3 C4 119.20(10) . . ?
C5 C6 C1 120.62(11) . . ?
C15 C14 C13 120.15(11) . . ?
C2 C1 C6 118.40(10) . . ?
C2 C1 C10 120.44(10) . . ?
C6 C1 C10 121.06(10) . . ?
C16 C17 C12 119.73(11) . . ?
C13 C12 C7 119.66(10) . . ?
C17 C12 C13 119.56(10) . . ?
C17 C12 C7 120.70(10) . . ?
C16 C15 C14 119.52(11) . . ?
C9 C8 C7 102.35(9) . . ?
O11 C10 C1 112.86(9) . . ?
C9 C10 O11 113.09(9) . . ?
C9 C10 C1 134.00(10) . . ?
O11 C7 C22 106.77(9) . . ?
O11 C7 C12 108.90(8) . . ?
O11 C7 C8 104.65(8) . . ?
C22 C7 C12 111.68(9) . . ?
C22 C7 C8 112.68(9) . . ?
C12 C7 C8 111.73(9) . . ?
O21 C18 O19 123.03(10) . . ?
O21 C18 C9 127.64(10) . . ?
O19 C18 C9 109.31(9) . . ?
O24 C4 C5 115.10(10) . . ?
O24 C4 C3 125.12(10) . . ?
C5 C4 C3 119.78(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
