# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_20250604_zm_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2542833'
loop_
_audit_author_name
_audit_author_address
'Feiying Ruan'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2026-04-01 deposited with the CCDC.	2026-05-20 downloaded from the CCDC.
;
_audit_creation_date             2025-06-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O3'
_chemical_formula_sum            'C18 H16 O3'
_chemical_formula_weight         280.31
_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      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                   13.3008(9)
_cell_length_b                   9.8645(5)
_cell_length_c                   10.7668(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.685(2)
_cell_angle_gamma                90
_cell_volume                     1399.98(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6218
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1761 before and 0.0624 after correction.
The Ratio of minimum to maximum transmission is 0.8340.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19285
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.579
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2210
_reflns_number_total             3190
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.053
_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)+(0.0417P)²+0.4531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1274
_refine_special_details          ?
_olex2_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C3(H3A), C6(H6), C14(H14), C2(H2), C18(H18), C1(H1), C17(H17),
  C16(H16), C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.66290(10) 0.49138(14) 0.49003(12) 0.0540(4) Uani 1 1 d . . . . .
O3 O 0.91420(10) 0.34275(15) 0.50417(12) 0.0570(4) Uani 1 1 d . . . . .
H3 H 0.925751 0.387510 0.568685 0.085 Uiso 1 1 calc R U . . .
O2 O 0.79359(12) 0.47229(17) 0.63447(12) 0.0673(4) Uani 1 1 d . . . . .
C8 C 0.66949(13) 0.27213(17) 0.29913(17) 0.0420(4) Uani 1 1 d . . . . .
H8 H 0.651804 0.198210 0.247168 0.050 Uiso 1 1 calc R U . . .
C5 C 0.41858(14) 0.41108(18) 0.21182(17) 0.0437(4) Uani 1 1 d . . . . .
H5 H 0.409922 0.442140 0.291252 0.052 Uiso 1 1 calc R U . . .
C4 C 0.51491(13) 0.37286(16) 0.18732(16) 0.0377(4) Uani 1 1 d . . . . .
C7 C 0.60505(13) 0.37615(17) 0.28533(16) 0.0389(4) Uani 1 1 d . . . . .
C13 C 0.84854(13) 0.48244(18) 0.33198(16) 0.0413(4) Uani 1 1 d . . . . .
C9 C 0.76610(14) 0.25753(18) 0.38629(17) 0.0461(4) Uani 1 1 d . . . . .
H9A H 0.812516 0.203823 0.344302 0.055 Uiso 1 1 calc R U . . .
H9B H 0.751567 0.206083 0.458580 0.055 Uiso 1 1 calc R U . . .
C3 C 0.52462(15) 0.32894(18) 0.06668(17) 0.0452(4) Uani 1 1 d . . . . .
H3A H 0.588173 0.303703 0.047630 0.054 Uiso 1 1 calc R U . . .
C11 C 0.75940(15) 0.45650(19) 0.52631(17) 0.0459(4) Uani 1 1 d . . . . .
C12 C 0.61814(15) 0.50472(19) 0.36021(18) 0.0494(5) Uani 1 1 d . . . . .
H12A H 0.660047 0.565976 0.318818 0.059 Uiso 1 1 calc R U . . .
H12B H 0.552083 0.546908 0.358407 0.059 Uiso 1 1 calc R U . . .
C10 C 0.82111(13) 0.38742(18) 0.43381(16) 0.0414(4) Uani 1 1 d . . . . .
C6 C 0.33585(15) 0.4035(2) 0.1198(2) 0.0533(5) Uani 1 1 d . . . . .
H6 H 0.272009 0.428534 0.138004 0.064 Uiso 1 1 calc R U . . .
C14 C 0.87573(16) 0.4295(2) 0.22154(19) 0.0572(5) Uani 1 1 d . . . . .
H14 H 0.868651 0.337089 0.205575 0.069 Uiso 1 1 calc R U . . .
C2 C 0.44219(16) 0.32208(19) -0.02494(19) 0.0535(5) Uani 1 1 d . . . . .
H2 H 0.450485 0.292414 -0.104926 0.064 Uiso 1 1 calc R U . . .
C18 C 0.85781(16) 0.6203(2) 0.3522(2) 0.0561(5) Uani 1 1 d . . . . .
H18 H 0.838790 0.657601 0.424908 0.067 Uiso 1 1 calc R U . . .
C1 C 0.34729(16) 0.3590(2) 0.0013(2) 0.0567(5) Uani 1 1 d . . . . .
H1 H 0.291477 0.353946 -0.060571 0.068 Uiso 1 1 calc R U . . .
C17 C 0.89517(17) 0.7038(3) 0.2654(2) 0.0710(7) Uani 1 1 d . . . . .
H17 H 0.900668 0.796633 0.279536 0.085 Uiso 1 1 calc R U . . .
C16 C 0.92404(17) 0.6487(3) 0.1584(2) 0.0755(8) Uani 1 1 d . . . . .
H16 H 0.951130 0.703899 0.101169 0.091 Uiso 1 1 calc R U . . .
C15 C 0.91282(19) 0.5120(3) 0.1360(2) 0.0746(7) Uani 1 1 d . . . . .
H15 H 0.930520 0.475266 0.062395 0.090 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 C11 1.336(2) . ?
O1 C12 1.450(2) . ?
O3 H3 0.8200 . ?
O3 C10 1.432(2) . ?
O2 C11 1.202(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.332(2) . ?
C8 C9 1.493(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.394(2) . ?
C5 C6 1.381(3) . ?
C4 C7 1.488(2) . ?
C4 C3 1.392(2) . ?
C7 C12 1.500(2) . ?
C13 C10 1.523(2) . ?
C13 C14 1.390(2) . ?
C13 C18 1.380(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.529(3) . ?
C3 H3A 0.9300 . ?
C3 C2 1.375(3) . ?
C11 C10 1.532(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C1 1.377(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.387(3) . ?
C1 H1 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.374(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.375(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
C11 O1 C12 124.04(14) . . ?
C10 O3 H3 109.5 . . ?
C7 C8 H8 115.4 . . ?
C7 C8 C9 129.12(17) . . ?
C9 C8 H8 115.4 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 120.93(17) . . ?
C5 C4 C7 122.25(15) . . ?
C3 C4 C5 117.59(16) . . ?
C3 C4 C7 120.15(15) . . ?
C8 C7 C4 120.50(16) . . ?
C8 C7 C12 124.36(17) . . ?
C4 C7 C12 115.10(15) . . ?
C14 C13 C10 119.95(17) . . ?
C18 C13 C10 121.16(17) . . ?
C18 C13 C14 118.51(18) . . ?
C8 C9 H9A 107.9 . . ?
C8 C9 H9B 107.9 . . ?
C8 C9 C10 117.54(15) . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 C4 121.36(18) . . ?
C2 C3 H3A 119.3 . . ?
O1 C11 C10 120.12(15) . . ?
O2 C11 O1 118.30(17) . . ?
O2 C11 C10 121.39(18) . . ?
O1 C12 C7 116.38(15) . . ?
O1 C12 H12A 108.2 . . ?
O1 C12 H12B 108.2 . . ?
C7 C12 H12A 108.2 . . ?
C7 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
O3 C10 C13 107.27(14) . . ?
O3 C10 C9 105.09(14) . . ?
O3 C10 C11 107.06(14) . . ?
C13 C10 C9 115.13(14) . . ?
C13 C10 C11 113.25(15) . . ?
C9 C10 C11 108.43(15) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.40(18) . . ?
C1 C6 H6 119.8 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.27(19) . . ?
C1 C2 H2 119.9 . . ?
C13 C18 H18 119.6 . . ?
C13 C18 C17 120.7(2) . . ?
C17 C18 H18 119.6 . . ?
C6 C1 C2 119.45(19) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.1 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?

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 C11 C10 O3 -170.60(16) . . . . ?
O1 C11 C10 C13 71.4(2) . . . . ?
O1 C11 C10 C9 -57.7(2) . . . . ?
O2 C11 C10 O3 4.3(2) . . . . ?
O2 C11 C10 C13 -113.7(2) . . . . ?
O2 C11 C10 C9 117.2(2) . . . . ?
C8 C7 C12 O1 -35.4(3) . . . . ?
C8 C9 C10 O3 -174.60(15) . . . . ?
C8 C9 C10 C13 -56.8(2) . . . . ?
C8 C9 C10 C11 71.2(2) . . . . ?
C5 C4 C7 C8 134.42(18) . . . . ?
C5 C4 C7 C12 -47.9(2) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C7 C12 O1 147.11(15) . . . . ?
C4 C3 C2 C1 0.0(3) . . . . ?
C7 C8 C9 C10 -24.1(3) . . . . ?
C7 C4 C3 C2 178.57(16) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C18 C17 C16 -0.5(3) . . . . ?
C9 C8 C7 C4 176.77(16) . . . . ?
C9 C8 C7 C12 -0.6(3) . . . . ?
C3 C4 C7 C8 -44.7(2) . . . . ?
C3 C4 C7 C12 132.90(18) . . . . ?
C3 C2 C1 C6 0.3(3) . . . . ?
C11 O1 C12 C7 68.6(2) . . . . ?
C12 O1 C11 O2 166.62(18) . . . . ?
C12 O1 C11 C10 -18.3(3) . . . . ?
C10 C13 C14 C15 -171.71(19) . . . . ?
C10 C13 C18 C17 171.77(18) . . . . ?
C6 C5 C4 C7 -178.24(16) . . . . ?
C6 C5 C4 C3 0.9(3) . . . . ?
C14 C13 C10 O3 81.9(2) . . . . ?
C14 C13 C10 C9 -34.7(2) . . . . ?
C14 C13 C10 C11 -160.20(17) . . . . ?
C14 C13 C18 C17 -1.2(3) . . . . ?
C18 C13 C10 O3 -90.9(2) . . . . ?
C18 C13 C10 C9 152.52(17) . . . . ?
C18 C13 C10 C11 27.0(2) . . . . ?
C18 C13 C14 C15 1.3(3) . . . . ?
C18 C17 C16 C15 2.0(3) . . . . ?
C17 C16 C15 C14 -1.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
