# 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. 
# 
#######################################################################

data_250926yu_z2004585_zcs_0m
_database_code_depnum_ccdc_archive 'CCDC 2492200'
loop_
_audit_author_name
_audit_author_address
'Xiaodi Yang'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2025-09-29 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;
_audit_creation_date             2025-09-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2025/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_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      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                   10.4888(2)
_cell_length_b                   5.67560(10)
_cell_length_c                   28.1025(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.0040(10)
_cell_angle_gamma                90
_cell_volume                     1660.46(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5038
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      3.17
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8826.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14793
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.402
_diffrn_reflns_theta_min         3.169
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III-M14'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_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                2466
_reflns_number_total             3043
_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 V8.41 (Bruker, 2024)'
_computing_data_collection       'APEX6 V2024.9-1 (Bruker, 2025)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.128
_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)+(0.0520P)²+1.2282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
;
_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 0.73597(17) 0.2571(3) 0.58140(6) 0.0377(4) Uani 1 1 d . . . . .
O2 O 0.34445(17) 1.1410(4) 0.67090(7) 0.0556(6) Uani 1 1 d . . . . .
O3 O 0.52719(16) 1.0500(4) 0.71651(6) 0.0450(5) Uani 1 1 d . . . . .
C1 C 0.6374(2) 0.8962(5) 0.71325(8) 0.0362(6) Uani 1 1 d . . . . .
H1A H 0.628432 0.745766 0.730375 0.043 Uiso 1 1 calc R U . . .
H1B H 0.718587 0.973611 0.726553 0.043 Uiso 1 1 calc R U . . .
C2 C 0.63283(19) 0.8568(4) 0.65967(7) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.663124 1.004700 0.645315 0.027 Uiso 1 1 calc R U . . .
C3 C 0.70556(19) 0.6519(4) 0.64076(7) 0.0217(5) Uani 1 1 d . . . . .
H3 H 0.671453 0.501498 0.652781 0.026 Uiso 1 1 calc R U . . .
C4 C 0.84846(19) 0.6671(4) 0.65813(7) 0.0212(5) Uani 1 1 d . . . . .
C5 C 0.9214(2) 0.8610(4) 0.64786(7) 0.0251(5) Uani 1 1 d . . . . .
H5 H 0.882282 0.983828 0.628264 0.030 Uiso 1 1 calc R U . . .
C6 C 1.0499(2) 0.8778(4) 0.66574(8) 0.0278(5) Uani 1 1 d . . . . .
H6 H 1.098198 1.011590 0.658292 0.033 Uiso 1 1 calc R U . . .
C7 C 1.1086(2) 0.7010(4) 0.69440(8) 0.0319(5) Uani 1 1 d . . . . .
H7 H 1.196985 0.712288 0.706555 0.038 Uiso 1 1 calc R U . . .
C8 C 1.0373(2) 0.5077(4) 0.70516(8) 0.0360(6) Uani 1 1 d . . . . .
H8 H 1.076708 0.385795 0.724940 0.043 Uiso 1 1 calc R U . . .
C9 C 0.9085(2) 0.4909(4) 0.68721(8) 0.0300(5) Uani 1 1 d . . . . .
H9 H 0.860516 0.357204 0.694874 0.036 Uiso 1 1 calc R U . . .
C10 C 0.67483(19) 0.6579(4) 0.58531(7) 0.0220(5) Uani 1 1 d . . . . .
H10 H 0.711138 0.806060 0.573167 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5281(2) 0.6540(4) 0.56943(8) 0.0313(5) Uani 1 1 d . . . . .
H11A H 0.512797 0.667443 0.534066 0.038 Uiso 1 1 calc R U . . .
H11B H 0.493477 0.500089 0.578368 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4547(2) 0.8500(4) 0.59139(8) 0.0333(6) Uani 1 1 d . . . . .
H12A H 0.478954 1.005248 0.579183 0.040 Uiso 1 1 calc R U . . .
H12B H 0.361034 0.828165 0.582811 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4887(2) 0.8388(4) 0.64526(8) 0.0305(5) Uani 1 1 d . . . . .
H13 H 0.459947 0.682291 0.656326 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4408(2) 1.0246(5) 0.67674(9) 0.0376(6) Uani 1 1 d . . . . .
C15 C 0.7327(2) 0.4499(4) 0.56214(7) 0.0234(5) Uani 1 1 d . . . . .
C16 C 0.78218(18) 0.4763(4) 0.51480(7) 0.0222(5) Uani 1 1 d . . . . .
C17 C 0.7566(2) 0.6744(4) 0.48586(7) 0.0264(5) Uani 1 1 d . . . . .
H17 H 0.707304 0.800428 0.496343 0.032 Uiso 1 1 calc R U . . .
C18 C 0.8031(2) 0.6877(4) 0.44171(8) 0.0320(5) Uani 1 1 d . . . . .
H18 H 0.783919 0.821348 0.421753 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8768(2) 0.5077(4) 0.42679(8) 0.0352(6) Uani 1 1 d . . . . .
H19 H 0.909334 0.518588 0.396760 0.042 Uiso 1 1 calc R U . . .
C20 C 0.9038(2) 0.3109(4) 0.45536(8) 0.0327(5) Uani 1 1 d . . . . .
H20 H 0.955177 0.187493 0.445079 0.039 Uiso 1 1 calc R U . . .
C21 C 0.8557(2) 0.2948(4) 0.49894(8) 0.0277(5) Uani 1 1 d . . . . .
H21 H 0.872949 0.158455 0.518255 0.033 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 C15 1.219(3) . ?
O2 C14 1.201(3) . ?
O3 C1 1.461(3) . ?
O3 C14 1.358(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.517(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.522(3) . ?
C2 C13 1.520(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.521(3) . ?
C3 C10 1.553(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C10 H10 1.0000 . ?
C10 C11 1.550(3) . ?
C10 C15 1.511(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.526(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.514(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.502(3) . ?
C15 C16 1.493(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9500 . ?

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
C14 O3 C1 109.81(18) . . ?
O3 C1 H1A 111.2 . . ?
O3 C1 H1B 111.2 . . ?
O3 C1 C2 102.76(17) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
C1 C2 H2 107.7 . . ?
C1 C2 C3 120.18(18) . . ?
C1 C2 C13 100.63(17) . . ?
C3 C2 H2 107.7 . . ?
C13 C2 H2 107.7 . . ?
C13 C2 C3 112.35(18) . . ?
C2 C3 H3 108.6 . . ?
C2 C3 C10 106.38(16) . . ?
C4 C3 C2 111.15(17) . . ?
C4 C3 H3 108.6 . . ?
C4 C3 C10 113.37(16) . . ?
C10 C3 H3 108.6 . . ?
C5 C4 C3 121.57(18) . . ?
C5 C4 C9 118.0(2) . . ?
C9 C4 C3 120.35(19) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C3 C10 H10 108.7 . . ?
C11 C10 C3 111.48(17) . . ?
C11 C10 H10 108.7 . . ?
C15 C10 C3 111.72(17) . . ?
C15 C10 H10 108.7 . . ?
C15 C10 C11 107.56(17) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.92(18) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 C11 107.73(19) . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
C2 C13 H13 107.8 . . ?
C12 C13 C2 111.69(18) . . ?
C12 C13 H13 107.8 . . ?
C14 C13 C2 100.93(18) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 107.8 . . ?
O2 C14 O3 121.3(2) . . ?
O2 C14 C13 129.9(2) . . ?
O3 C14 C13 108.7(2) . . ?
O1 C15 C10 120.04(19) . . ?
O1 C15 C16 119.46(19) . . ?
C16 C15 C10 120.46(18) . . ?
C17 C16 C15 122.51(19) . . ?
C21 C16 C15 118.48(19) . . ?
C21 C16 C17 119.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.7(2) . . ?
C20 C21 H21 119.6 . . ?

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 C15 C16 C17 165.6(2) . . . . ?
O1 C15 C16 C21 -13.9(3) . . . . ?
O3 C1 C2 C3 -162.05(19) . . . . ?
O3 C1 C2 C13 -38.2(2) . . . . ?
C1 O3 C14 O2 -177.3(2) . . . . ?
C1 O3 C14 C13 2.6(3) . . . . ?
C1 C2 C3 C4 -58.7(2) . . . . ?
C1 C2 C3 C10 177.46(19) . . . . ?
C1 C2 C13 C12 167.9(2) . . . . ?
C1 C2 C13 C14 38.9(2) . . . . ?
C2 C3 C4 C5 -59.0(2) . . . . ?
C2 C3 C4 C9 117.5(2) . . . . ?
C2 C3 C10 C11 -54.8(2) . . . . ?
C2 C3 C10 C15 -175.22(16) . . . . ?
C2 C13 C14 O2 152.9(3) . . . . ?
C2 C13 C14 O3 -26.9(2) . . . . ?
C3 C2 C13 C12 -63.0(2) . . . . ?
C3 C2 C13 C14 168.01(18) . . . . ?
C3 C4 C5 C6 176.95(19) . . . . ?
C3 C4 C9 C8 -177.0(2) . . . . ?
C3 C10 C11 C12 55.2(3) . . . . ?
C3 C10 C15 O1 37.0(3) . . . . ?
C3 C10 C15 C16 -145.08(18) . . . . ?
C4 C3 C10 C11 -177.30(18) . . . . ?
C4 C3 C10 C15 62.3(2) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C4 C9 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C10 C3 C4 C5 60.8(3) . . . . ?
C10 C3 C4 C9 -122.7(2) . . . . ?
C10 C11 C12 C13 -53.6(3) . . . . ?
C10 C15 C16 C17 -12.3(3) . . . . ?
C10 C15 C16 C21 168.25(19) . . . . ?
C11 C10 C15 O1 -85.6(2) . . . . ?
C11 C10 C15 C16 92.3(2) . . . . ?
C11 C12 C13 C2 56.3(3) . . . . ?
C11 C12 C13 C14 174.3(2) . . . . ?
C12 C13 C14 O2 29.7(4) . . . . ?
C12 C13 C14 O3 -150.1(2) . . . . ?
C13 C2 C3 C4 -176.71(17) . . . . ?
C13 C2 C3 C10 59.4(2) . . . . ?
C14 O3 C1 C2 23.0(3) . . . . ?
C15 C10 C11 C12 178.03(19) . . . . ?
C15 C16 C17 C18 -178.8(2) . . . . ?
C15 C16 C21 C20 -179.9(2) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C17 C16 C21 C20 0.6(3) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C16 -1.1(3) . . . . ?
C21 C16 C17 C18 0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
####################################################################### 
# 
# 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_251014ha_z1160218_0m
_database_code_depnum_ccdc_archive 'CCDC 2495478'
loop_
_audit_author_name
_audit_author_address
'Yun-Xuan Tan'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;
_audit_creation_date             2025-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_chemical_absolute_configuration unk
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.4404(9)
_cell_length_b                   5.6542(4)
_cell_length_c                   13.1370(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.208(6)
_cell_angle_gamma                90
_cell_volume                     827.30(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2002
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.84
_cell_measurement_theta_min      3.46
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6343
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1278 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.8423.
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    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5617
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.260
_diffrn_reflns_theta_min         3.456
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.836
_reflns_Friedel_fraction_max     0.831
_reflns_number_gt                2276
_reflns_number_total             2796
_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 V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.077
_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)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_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 0.3609(2) 0.5076(6) 0.8424(2) 0.0633(9) Uani 1 1 d . . . . .
O2 O 0.5412(2) 0.4652(5) 0.94892(16) 0.0402(6) Uani 1 1 d . . . . .
O3 O 0.6889(2) 0.1966(4) 0.62607(17) 0.0432(6) Uani 1 1 d . . . . .
C1 C 0.4632(3) 0.5719(7) 0.8690(2) 0.0394(8) Uani 1 1 d . . . . .
C2 C 0.5248(3) 0.7693(6) 0.8244(2) 0.0334(7) Uani 1 1 d . . . . .
H2 H 0.510681 0.919515 0.859911 0.040 Uiso 1 1 calc R U . . .
C3 C 0.6574(3) 0.7043(6) 0.8620(2) 0.0284(7) Uani 1 1 d . . . . .
H3 H 0.708544 0.849682 0.872972 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7028(3) 0.5273(5) 0.7900(2) 0.0242(6) Uani 1 1 d . . . . .
H4 H 0.667414 0.369589 0.799889 0.029 Uiso 1 1 calc R U . . .
C5 C 0.8377(3) 0.5016(5) 0.8221(2) 0.0241(6) Uani 1 1 d . . . . .
C6 C 0.8899(3) 0.3027(6) 0.8762(2) 0.0304(7) Uani 1 1 d . . . . .
H6 H 0.839778 0.181440 0.892687 0.036 Uiso 1 1 calc R U . . .
C7 C 1.0134(3) 0.2775(6) 0.9066(3) 0.0383(8) Uani 1 1 d . . . . .
H7 H 1.046958 0.141202 0.944594 0.046 Uiso 1 1 calc R U . . .
C8 C 1.0880(3) 0.4499(7) 0.8820(2) 0.0371(8) Uani 1 1 d . . . . .
H8 H 1.172768 0.431408 0.901501 0.045 Uiso 1 1 calc R U . . .
C9 C 1.0379(3) 0.6497(6) 0.8287(2) 0.0354(8) Uani 1 1 d . . . . .
H9 H 1.088706 0.769663 0.812167 0.043 Uiso 1 1 calc R U . . .
C10 C 0.9145(3) 0.6768(6) 0.7991(2) 0.0303(7) Uani 1 1 d . . . . .
H10 H 0.881537 0.815507 0.762887 0.036 Uiso 1 1 calc R U . . .
C11 C 0.6591(3) 0.5937(5) 0.6734(2) 0.0252(6) Uani 1 1 d . . . . .
H11 H 0.693631 0.750508 0.660750 0.030 Uiso 1 1 calc R U . . .
C12 C 0.5222(3) 0.6094(6) 0.6446(2) 0.0337(7) Uani 1 1 d . . . . .
H12A H 0.494594 0.643170 0.568938 0.040 Uiso 1 1 calc R U . . .
H12B H 0.487586 0.455811 0.658867 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4780(3) 0.8033(7) 0.7070(2) 0.0377(8) Uani 1 1 d . . . . .
H13A H 0.389088 0.803009 0.690312 0.045 Uiso 1 1 calc R U . . .
H13B H 0.504822 0.958879 0.686368 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7035(3) 0.4060(5) 0.6083(2) 0.0281(7) Uani 1 1 d . . . . .
C15 C 0.7636(3) 0.4755(5) 0.5240(2) 0.0270(6) Uani 1 1 d . . . . .
C16 C 0.8429(3) 0.3177(6) 0.4948(2) 0.0357(7) Uani 1 1 d . . . . .
H16 H 0.858883 0.170210 0.529874 0.043 Uiso 1 1 calc R U . . .
C17 C 0.8988(4) 0.3731(6) 0.4153(3) 0.0453(9) Uani 1 1 d . . . . .
H17 H 0.954749 0.266031 0.397258 0.054 Uiso 1 1 calc R U . . .
C18 C 0.8735(4) 0.5835(7) 0.3621(3) 0.0443(9) Uani 1 1 d . . . . .
H18 H 0.911383 0.620497 0.306814 0.053 Uiso 1 1 calc R U . . .
C19 C 0.7927(3) 0.7417(6) 0.3889(2) 0.0410(9) Uani 1 1 d . . . . .
H19 H 0.773381 0.884385 0.350508 0.049 Uiso 1 1 calc R U . . .
C20 C 0.7403(3) 0.6913(6) 0.4716(2) 0.0318(7) Uani 1 1 d . . . . .
H20 H 0.688606 0.803410 0.492657 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6566(3) 0.5856(7) 0.9671(2) 0.0375(8) Uani 1 1 d . . . . .
H21A H 0.723504 0.471429 0.986843 0.045 Uiso 1 1 calc R U . . .
H21B H 0.663476 0.705005 1.023304 0.045 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 1.199(4) . ?
O2 C1 1.354(4) . ?
O2 C21 1.456(4) . ?
O3 C14 1.225(4) . ?
C1 C2 1.508(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.529(4) . ?
C2 C13 1.525(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.545(4) . ?
C3 C21 1.537(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.512(4) . ?
C4 C11 1.546(4) . ?
C5 C6 1.390(4) . ?
C5 C10 1.402(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.528(4) . ?
C11 C14 1.522(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.523(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.484(4) . ?
C15 C16 1.388(4) . ?
C15 C20 1.396(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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 C21 109.3(3) . . ?
O1 C1 O2 121.1(3) . . ?
O1 C1 C2 128.6(3) . . ?
O2 C1 C2 110.3(3) . . ?
C1 C2 H2 107.9 . . ?
C1 C2 C3 102.4(3) . . ?
C1 C2 C13 113.5(3) . . ?
C3 C2 H2 107.9 . . ?
C13 C2 H2 107.9 . . ?
C13 C2 C3 116.8(3) . . ?
C2 C3 H3 110.7 . . ?
C2 C3 C4 113.9(2) . . ?
C2 C3 C21 100.7(2) . . ?
C4 C3 H3 110.7 . . ?
C21 C3 H3 110.7 . . ?
C21 C3 C4 109.8(3) . . ?
C3 C4 H4 107.2 . . ?
C3 C4 C11 111.8(2) . . ?
C5 C4 C3 110.9(2) . . ?
C5 C4 H4 107.2 . . ?
C5 C4 C11 112.2(2) . . ?
C11 C4 H4 107.2 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 C10 117.7(3) . . ?
C10 C5 C4 121.5(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C4 C11 H11 109.2 . . ?
C12 C11 C4 109.9(2) . . ?
C12 C11 H11 109.2 . . ?
C14 C11 C4 108.3(2) . . ?
C14 C11 H11 109.2 . . ?
C14 C11 C12 110.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 C11 110.9(3) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C2 C13 H13A 109.3 . . ?
C2 C13 H13B 109.3 . . ?
C12 C13 C2 111.8(3) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O3 C14 C11 119.3(3) . . ?
O3 C14 C15 120.3(3) . . ?
C15 C14 C11 120.4(3) . . ?
C16 C15 C14 118.7(3) . . ?
C16 C15 C20 119.3(3) . . ?
C20 C15 C14 122.0(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
O2 C21 C3 104.4(2) . . ?
O2 C21 H21A 110.9 . . ?
O2 C21 H21B 110.9 . . ?
C3 C21 H21A 110.9 . . ?
C3 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?

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 C1 C2 C3 -160.1(4) . . . . ?
O1 C1 C2 C13 -33.4(5) . . . . ?
O2 C1 C2 C3 20.0(3) . . . . ?
O2 C1 C2 C13 146.7(3) . . . . ?
O3 C14 C15 C16 -25.4(4) . . . . ?
O3 C14 C15 C20 152.9(3) . . . . ?
C1 O2 C21 C3 -24.1(3) . . . . ?
C1 C2 C3 C4 85.1(3) . . . . ?
C1 C2 C3 C21 -32.3(3) . . . . ?
C1 C2 C13 C12 -74.4(4) . . . . ?
C2 C3 C4 C5 170.9(2) . . . . ?
C2 C3 C4 C11 44.9(3) . . . . ?
C2 C3 C21 O2 34.7(3) . . . . ?
C3 C2 C13 C12 44.3(4) . . . . ?
C3 C4 C5 C6 104.0(3) . . . . ?
C3 C4 C5 C10 -75.7(3) . . . . ?
C3 C4 C11 C12 -56.5(3) . . . . ?
C3 C4 C11 C14 -177.8(2) . . . . ?
C4 C3 C21 O2 -85.7(3) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C4 C5 C10 C9 -179.7(3) . . . . ?
C4 C11 C12 C13 62.3(3) . . . . ?
C4 C11 C14 O3 48.4(4) . . . . ?
C4 C11 C14 C15 -131.8(3) . . . . ?
C5 C4 C11 C12 178.2(2) . . . . ?
C5 C4 C11 C14 56.9(3) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C6 C5 C10 C9 0.6(4) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
C8 C9 C10 C5 -0.4(5) . . . . ?
C10 C5 C6 C7 0.1(4) . . . . ?
C11 C4 C5 C6 -130.2(3) . . . . ?
C11 C4 C5 C10 50.1(4) . . . . ?
C11 C12 C13 C2 -55.3(3) . . . . ?
C11 C14 C15 C16 154.8(3) . . . . ?
C11 C14 C15 C20 -26.9(4) . . . . ?
C12 C11 C14 O3 -72.3(4) . . . . ?
C12 C11 C14 C15 107.5(3) . . . . ?
C13 C2 C3 C4 -39.5(4) . . . . ?
C13 C2 C3 C21 -156.9(3) . . . . ?
C14 C11 C12 C13 -178.0(2) . . . . ?
C14 C15 C16 C17 178.6(3) . . . . ?
C14 C15 C20 C19 -175.8(3) . . . . ?
C15 C16 C17 C18 -1.9(5) . . . . ?
C16 C15 C20 C19 2.5(4) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C17 C18 C19 C20 2.1(5) . . . . ?
C18 C19 C20 C15 -3.7(5) . . . . ?
C20 C15 C16 C17 0.3(5) . . . . ?
C21 O2 C1 O1 -177.4(3) . . . . ?
C21 O2 C1 C2 2.5(4) . . . . ?
C21 C3 C4 C5 -77.0(3) . . . . ?
C21 C3 C4 C11 156.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
