# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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. 
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data_cu_240529chmx_0m
_database_code_depnum_ccdc_archive 'CCDC 2358966'
loop_
_audit_author_name
_audit_author_address
CH-BT
;Guizhou university
China
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_audit_creation_date             2024-05-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O4'
_chemical_formula_sum            'C15 H10 O4'
_chemical_formula_weight         254.23
_chemical_absolute_configuration ad
_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 0.0181 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'

_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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.0759(2)
_cell_length_b                   7.1675(4)
_cell_length_c                   10.4870(6)
_cell_angle_alpha                96.968(3)
_cell_angle_beta                 93.261(3)
_cell_angle_gamma                91.060(3)
_cell_volume                     303.51(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3368
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      68.207
_cell_measurement_theta_min      4.255
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.6916.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             132
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3501
_diffrn_reflns_point_group_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         4.255
_diffrn_ambient_temperature      303.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.661
_reflns_Friedel_fraction_max     0.659
_reflns_number_gt                1760
_reflns_number_total             1768
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1768
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.0212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_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
O1 O 0.3325(8) -0.0159(3) 0.2998(3) 0.0891(8) Uani 1 1 d . . . . .
O2 O 0.5227(5) 0.1939(2) 0.46520(18) 0.0583(5) Uani 1 1 d . . . . .
O3 O 0.5233(4) 0.5113(2) 0.54581(14) 0.0485(4) Uani 1 1 d . . . . .
O4 O 0.6641(6) 0.4174(2) 0.73849(17) 0.0628(5) Uani 1 1 d . . . . .
C1 C 0.4796(7) 0.1283(4) 0.3356(3) 0.0586(7) Uani 1 1 d . . . . .
C2 C 0.6375(6) 0.2651(3) 0.2634(2) 0.0476(5) Uani 1 1 d . . . . .
C3 C 0.6524(7) 0.2677(4) 0.1317(2) 0.0595(7) Uani 1 1 d . . . . .
H3 H 0.563655 0.169312 0.073145 0.071 Uiso 1 1 calc R U . . .
C4 C 0.8035(8) 0.4214(4) 0.0910(3) 0.0639(7) Uani 1 1 d . . . . .
H4 H 0.818217 0.427193 0.003433 0.077 Uiso 1 1 calc R U . . .
C5 C 0.9343(8) 0.5679(4) 0.1791(3) 0.0637(7) Uani 1 1 d . . . . .
H5 H 1.034894 0.670425 0.149296 0.076 Uiso 1 1 calc R U . . .
C6 C 0.9184(7) 0.5648(3) 0.3099(3) 0.0540(6) Uani 1 1 d . . . . .
H6 H 1.005945 0.663262 0.368680 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7677(5) 0.4102(3) 0.3503(2) 0.0429(5) Uani 1 1 d . . . . .
C8 C 0.7097(6) 0.3674(3) 0.4828(2) 0.0459(5) Uani 1 1 d . . . . .
H8 H 0.918493 0.353889 0.531510 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5337(6) 0.5287(3) 0.6773(2) 0.0448(5) Uani 1 1 d . . . . .
C10 C 0.3662(6) 0.7002(3) 0.7297(2) 0.0437(5) Uani 1 1 d . . . . .
C11 C 0.2850(7) 0.8413(3) 0.6539(2) 0.0529(6) Uani 1 1 d . . . . .
H11 H 0.331387 0.827944 0.567541 0.063 Uiso 1 1 calc R U . . .
C12 C 0.1360(8) 1.0004(4) 0.7074(3) 0.0636(7) Uani 1 1 d . . . . .
H12 H 0.082761 1.094901 0.656920 0.076 Uiso 1 1 calc R U . . .
C13 C 0.0653(8) 1.0207(4) 0.8350(3) 0.0641(7) Uani 1 1 d . . . . .
H13 H -0.037347 1.128164 0.870184 0.077 Uiso 1 1 calc R U . . .
C14 C 0.1460(8) 0.8829(4) 0.9103(2) 0.0628(7) Uani 1 1 d . . . . .
H14 H 0.099217 0.897640 0.996707 0.075 Uiso 1 1 calc R U . . .
C15 C 0.2959(7) 0.7226(3) 0.8588(2) 0.0536(6) Uani 1 1 d . . . . .
H15 H 0.350082 0.629501 0.910272 0.064 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
O1 C1 1.194(3) . ?
O2 C1 1.383(4) . ?
O2 C8 1.433(3) . ?
O3 C8 1.414(3) . ?
O3 C9 1.368(3) . ?
O4 C9 1.197(3) . ?
C1 C2 1.471(4) . ?
C2 C3 1.389(3) . ?
C2 C7 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C7 C8 1.489(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.479(3) . ?
C10 C11 1.393(3) . ?
C10 C15 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(4) . ?
C15 H15 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
C1 O2 C8 110.11(18) . . ?
C9 O3 C8 117.23(17) . . ?
O1 C1 O2 121.0(3) . . ?
O1 C1 C2 131.1(3) . . ?
O2 C1 C2 107.9(2) . . ?
C3 C2 C1 130.3(2) . . ?
C7 C2 C1 108.0(2) . . ?
C7 C2 C3 121.6(2) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 C2 117.4(2) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 121.2 . . ?
C7 C6 C5 117.5(2) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 C6 121.2(2) . . ?
C2 C7 C8 108.75(19) . . ?
C6 C7 C8 130.1(2) . . ?
O2 C8 C7 105.14(18) . . ?
O2 C8 H8 110.8 . . ?
O3 C8 O2 109.76(19) . . ?
O3 C8 C7 109.44(17) . . ?
O3 C8 H8 110.8 . . ?
C7 C8 H8 110.8 . . ?
O3 C9 C10 110.87(17) . . ?
O4 C9 O3 122.8(2) . . ?
O4 C9 C10 126.3(2) . . ?
C11 C10 C9 121.73(19) . . ?
C15 C10 C9 118.87(19) . . ?
C15 C10 C11 119.4(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.9(2) . . ?
C14 C15 H15 120.0 . . ?

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 C1 C2 C3 2.0(5) . . . . ?
O1 C1 C2 C7 178.6(3) . . . . ?
O2 C1 C2 C3 -177.4(3) . . . . ?
O2 C1 C2 C7 -0.7(3) . . . . ?
O3 C9 C10 C11 -14.0(3) . . . . ?
O3 C9 C10 C15 167.7(2) . . . . ?
O4 C9 C10 C11 165.8(3) . . . . ?
O4 C9 C10 C15 -12.6(4) . . . . ?
C1 O2 C8 O3 120.2(2) . . . . ?
C1 O2 C8 C7 2.6(3) . . . . ?
C1 C2 C3 C4 176.3(3) . . . . ?
C1 C2 C7 C6 -176.8(2) . . . . ?
C1 C2 C7 C8 2.4(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C2 C7 C8 O2 -3.1(2) . . . . ?
C2 C7 C8 O3 -120.9(2) . . . . ?
C3 C2 C7 C6 0.1(4) . . . . ?
C3 C2 C7 C8 179.3(2) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C5 C6 C7 C8 -179.2(2) . . . . ?
C6 C7 C8 O2 176.0(2) . . . . ?
C6 C7 C8 O3 58.2(3) . . . . ?
C7 C2 C3 C4 0.1(4) . . . . ?
C8 O2 C1 O1 179.3(3) . . . . ?
C8 O2 C1 C2 -1.3(3) . . . . ?
C8 O3 C9 O4 -7.7(3) . . . . ?
C8 O3 C9 C10 172.06(18) . . . . ?
C9 O3 C8 O2 85.3(2) . . . . ?
C9 O3 C8 C7 -159.85(18) . . . . ?
C9 C10 C11 C12 -178.5(2) . . . . ?
C9 C10 C15 C14 178.7(2) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?
C15 C10 C11 C12 -0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
