# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_xjy-31
_database_code_depnum_ccdc_archive 'CCDC 2453116'
loop_
_audit_author_name
_audit_author_address
'Sheng Lin'
;Beijing University of Chinese Medicine
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-14
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H30 O3, H2 O'
_chemical_formula_sum            'C20 H32 O4'
_chemical_formula_weight         336.45
_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      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                   6.84365(12)
_cell_length_b                   11.17471(20)
_cell_length_c                   11.9856(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.9687(16)
_cell_angle_gamma                90
_cell_volume                     915.38(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6028
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.7660
_cell_measurement_theta_min      3.6390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.15
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6787
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.072
_diffrn_reflns_theta_min         3.693
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -37.00 120.00   99
  2  ω   -113.00 -63.00   1.00    1.00    --  -40.73-142.00 162.00   50
  3  ω    -96.00  -2.00   1.00    1.00    --  -40.73 125.00-180.00   94
  4  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -37.00  30.00   99
  5  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00 -30.00   81
  6  ω    -34.00  65.00   1.00    1.00    --   40.73 -37.00 -30.00   99
  7  ω     79.00 178.00   1.00    1.00    --  107.58  30.00 150.00   99
  8  ω     34.00 122.00   1.00    1.00    --  107.58-125.00-150.00   88
  9  ω     37.00  88.00   1.00    1.00    --  107.58 -45.00  30.00   51
 10  ω     34.00 109.00   1.00    1.00    --  107.58 -94.00  60.00   75
 11  ω     35.00 122.00   1.00    1.00    --  107.58-128.00 -26.00   87
 12  ω     77.00 152.00   1.00    1.00    --  107.58  77.00  60.00   75
 13  ω    152.00 177.00   1.00    1.00    --  107.58 125.00 -30.00   25
 14  ω    116.00 178.00   1.00    1.00    --  107.58  30.00 -30.00   62
 15  ω    127.00 171.00   1.00    1.00    --  107.58 125.00 120.00   44
 16  ω    106.00 155.00   1.00    1.00    --  107.58 125.00  90.00   49
 17  ω     36.00 113.00   1.00    1.00    --  107.58 -45.00 150.00   77
 18  ω     96.00 128.00   1.00    1.00    --  107.58 125.00 150.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0377279000
_diffrn_orient_matrix_UB_12      -0.1351476000
_diffrn_orient_matrix_UB_13      -0.0121759000
_diffrn_orient_matrix_UB_21      -0.2114457000
_diffrn_orient_matrix_UB_22      -0.0262827000
_diffrn_orient_matrix_UB_23      0.0309501000
_diffrn_orient_matrix_UB_31      -0.0684247000
_diffrn_orient_matrix_UB_32      0.0068284000
_diffrn_orient_matrix_UB_33      -0.1243424000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3526
_reflns_number_total             3579
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1597 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(9)
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.003
_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)+(0.0632P)²+0.0291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0843
_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 C(H,H,H) groups, All O(H) groups
2.a Free rotating group:
 O4(H4A)
2.b Ternary CH refined with riding coordinates:
 C3(H3A), C5(H5), C14(H14), C15(H15)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C12(H12A,H12B), C16(H16A,H16B)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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 0.74567(19) 0.46362(15) -0.11038(10) 0.0389(3) Uani 1 1 d . . . . .
H1 H 0.656291 0.487184 -0.155826 0.058 Uiso 1 1 calc R U . . .
O2 O 0.78186(18) 0.64463(13) 0.60386(10) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.44313(17) 0.55240(14) 0.75190(10) 0.0351(3) Uani 1 1 d . . . . .
H3 H 0.325457 0.532003 0.755348 0.053 Uiso 1 1 calc R U . . .
C1 C 0.6230(3) 0.6587(2) 0.13369(14) 0.0380(4) Uani 1 1 d . . . . .
H1A H 0.488008 0.628190 0.139292 0.046 Uiso 1 1 calc R U . . .
H1B H 0.619549 0.746674 0.142810 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6939(3) 0.6288(2) 0.01814(15) 0.0392(5) Uani 1 1 d . . . . .
H2A H 0.605743 0.666056 -0.040025 0.047 Uiso 1 1 calc R U . . .
H2B H 0.826951 0.661692 0.010849 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6973(2) 0.49451(19) 0.00122(14) 0.0323(4) Uani 1 1 d . . . . .
H3A H 0.562901 0.463419 0.012905 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8398(2) 0.43071(16) 0.08477(13) 0.0273(4) Uani 1 1 d . . . . .
C5 C 0.7850(2) 0.46834(15) 0.20454(13) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.654238 0.430978 0.214482 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9201(2) 0.41308(16) 0.29651(14) 0.0275(3) Uani 1 1 d . . . . .
H6A H 0.922566 0.325099 0.286984 0.033 Uiso 1 1 calc R U . . .
H6B H 1.054834 0.443384 0.289418 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8539(2) 0.44243(15) 0.41031(14) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.900352 0.394456 0.471520 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7326(2) 0.53284(15) 0.43011(13) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.6563(3) 0.61220(16) 0.34033(14) 0.0274(3) Uani 1 1 d . . . . .
C10 C 0.7547(2) 0.60431(15) 0.22826(14) 0.0276(3) Uani 1 1 d . . . . .
C11 C 0.5117(3) 0.68882(17) 0.35960(14) 0.0334(4) Uani 1 1 d . . . . .
H11 H 0.464069 0.737941 0.299470 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4198(3) 0.70237(17) 0.46970(15) 0.0337(4) Uani 1 1 d . . . . .
H12A H 0.276909 0.712652 0.455705 0.040 Uiso 1 1 calc R U . . .
H12B H 0.470910 0.776276 0.506194 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4553(2) 0.59713(16) 0.55074(13) 0.0269(3) Uani 1 1 d . . . . .
C14 C 0.6659(2) 0.55248(15) 0.54611(13) 0.0255(3) Uani 1 1 d . . . . .
H14 H 0.679871 0.475948 0.589025 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4581(2) 0.64487(17) 0.67122(13) 0.0293(4) Uani 1 1 d . . . . .
H15 H 0.353983 0.706597 0.679439 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6614(3) 0.70074(19) 0.68476(15) 0.0346(4) Uani 1 1 d . . . . .
H16A H 0.653695 0.788077 0.671401 0.042 Uiso 1 1 calc R U . . .
H16B H 0.717876 0.687039 0.761407 0.042 Uiso 1 1 calc R U . . .
C17 C 0.3059(3) 0.49881(19) 0.52575(16) 0.0355(4) Uani 1 1 d . . . . .
H17A H 0.330583 0.432051 0.577597 0.053 Uiso 1 1 calc R U . . .
H17B H 0.316911 0.470720 0.448868 0.053 Uiso 1 1 calc R U . . .
H17C H 0.173977 0.530269 0.534655 0.053 Uiso 1 1 calc R U . . .
C18 C 0.8055(3) 0.29526(18) 0.07206(17) 0.0399(5) Uani 1 1 d . . . . .
H18A H 0.905446 0.251879 0.117479 0.060 Uiso 1 1 calc R U . . .
H18B H 0.813689 0.272610 -0.006547 0.060 Uiso 1 1 calc R U . . .
H18C H 0.675576 0.274983 0.097168 0.060 Uiso 1 1 calc R U . . .
C19 C 1.0532(2) 0.4563(2) 0.05785(16) 0.0360(4) Uani 1 1 d . . . . .
H19A H 1.074151 0.543025 0.055003 0.054 Uiso 1 1 calc R U . . .
H19B H 1.079937 0.420983 -0.014611 0.054 Uiso 1 1 calc R U . . .
H19C H 1.141493 0.421357 0.116033 0.054 Uiso 1 1 calc R U . . .
C20 C 0.9468(3) 0.67582(19) 0.24207(17) 0.0400(5) Uani 1 1 d . . . . .
H20A H 1.030826 0.640237 0.301925 0.060 Uiso 1 1 calc R U . . .
H20B H 0.917580 0.758972 0.261121 0.060 Uiso 1 1 calc R U . . .
H20C H 1.014343 0.673735 0.171961 0.060 Uiso 1 1 calc R U . . .
O4 O 0.0516(2) 0.52275(19) 0.75432(13) 0.0520(5) Uani 1 1 d G . . . .
H4A H -0.026121 0.501501 0.803646 0.078 Uiso 1 1 d G U . . .
H4B H -0.013(5) 0.567(3) 0.700(3) 0.059(8) Uiso 1 1 d . . . . .


_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 H1 0.8400 . ?
O1 C3 1.437(2) . ?
O2 C14 1.453(2) . ?
O2 C16 1.448(2) . ?
O3 H3 0.8400 . ?
O3 C15 1.423(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.528(2) . ?
C1 C10 1.536(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.514(3) . ?
C3 H3A 1.0000 . ?
C3 C4 1.536(2) . ?
C4 C5 1.560(2) . ?
C4 C18 1.538(3) . ?
C4 C19 1.539(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.532(2) . ?
C5 C10 1.562(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.496(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.336(2) . ?
C8 C9 1.469(2) . ?
C8 C14 1.502(2) . ?
C9 C10 1.536(2) . ?
C9 C11 1.338(3) . ?
C10 C20 1.541(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.499(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.537(3) . ?
C13 C14 1.529(2) . ?
C13 C15 1.539(2) . ?
C13 C17 1.520(2) . ?
C14 H14 1.0000 . ?
C15 H15 1.0000 . ?
C15 C16 1.526(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O4 H4A 0.8494 . ?
O4 H4B 0.91(3) . ?

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
C3 O1 H1 109.5 . . ?
C16 O2 C14 108.05(12) . . ?
C15 O3 H3 109.5 . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C2 C1 C10 112.37(15) . . ?
C10 C1 H1A 109.1 . . ?
C10 C1 H1B 109.1 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.23(16) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
O1 C3 C2 111.63(16) . . ?
O1 C3 H3A 107.7 . . ?
O1 C3 C4 109.05(14) . . ?
C2 C3 H3A 107.7 . . ?
C2 C3 C4 112.72(16) . . ?
C4 C3 H3A 107.7 . . ?
C3 C4 C5 107.44(13) . . ?
C3 C4 C18 107.69(16) . . ?
C3 C4 C19 110.74(14) . . ?
C18 C4 C5 108.28(13) . . ?
C18 C4 C19 107.70(15) . . ?
C19 C4 C5 114.76(14) . . ?
C4 C5 H5 104.9 . . ?
C4 C5 C10 118.06(13) . . ?
C6 C5 C4 112.86(13) . . ?
C6 C5 H5 104.9 . . ?
C6 C5 C10 110.01(14) . . ?
C10 C5 H5 104.9 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.58(13) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7 118.4 . . ?
C8 C7 C6 123.22(15) . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 121.79(15) . . ?
C7 C8 C14 119.76(15) . . ?
C9 C8 C14 118.42(14) . . ?
C8 C9 C10 116.76(14) . . ?
C11 C9 C8 119.88(15) . . ?
C11 C9 C10 123.33(15) . . ?
C1 C10 C5 109.19(14) . . ?
C1 C10 C9 110.83(14) . . ?
C1 C10 C20 109.82(16) . . ?
C9 C10 C5 106.47(13) . . ?
C9 C10 C20 106.66(14) . . ?
C20 C10 C5 113.80(14) . . ?
C9 C11 H11 117.8 . . ?
C9 C11 C12 124.38(16) . . ?
C12 C11 H11 117.8 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C11 C12 C13 114.80(14) . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C12 C13 C15 108.77(15) . . ?
C14 C13 C12 110.20(14) . . ?
C14 C13 C15 100.45(13) . . ?
C17 C13 C12 110.24(15) . . ?
C17 C13 C14 112.49(14) . . ?
C17 C13 C15 114.28(14) . . ?
O2 C14 C8 111.08(13) . . ?
O2 C14 C13 104.12(13) . . ?
O2 C14 H14 109.0 . . ?
C8 C14 C13 114.44(13) . . ?
C8 C14 H14 109.0 . . ?
C13 C14 H14 109.0 . . ?
O3 C15 C13 112.85(15) . . ?
O3 C15 H15 110.9 . . ?
O3 C15 C16 108.78(14) . . ?
C13 C15 H15 110.9 . . ?
C16 C15 C13 102.04(13) . . ?
C16 C15 H15 110.9 . . ?
O2 C16 C15 107.42(14) . . ?
O2 C16 H16A 110.2 . . ?
O2 C16 H16B 110.2 . . ?
C15 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H4A O4 H4B 110.4 . . ?

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 C3 C4 C5 178.97(14) . . . . ?
O1 C3 C4 C18 -64.59(18) . . . . ?
O1 C3 C4 C19 52.9(2) . . . . ?
O3 C15 C16 O2 96.85(16) . . . . ?
C1 C2 C3 O1 174.55(14) . . . . ?
C1 C2 C3 C4 -62.3(2) . . . . ?
C2 C1 C10 C5 -50.6(2) . . . . ?
C2 C1 C10 C9 -167.58(17) . . . . ?
C2 C1 C10 C20 74.8(2) . . . . ?
C2 C3 C4 C5 54.41(19) . . . . ?
C2 C3 C4 C18 170.85(15) . . . . ?
C2 C3 C4 C19 -71.64(19) . . . . ?
C3 C4 C5 C6 -178.53(14) . . . . ?
C3 C4 C5 C10 -48.33(19) . . . . ?
C4 C5 C6 C7 -175.23(14) . . . . ?
C4 C5 C10 C1 47.12(19) . . . . ?
C4 C5 C10 C9 166.83(13) . . . . ?
C4 C5 C10 C20 -75.96(19) . . . . ?
C5 C6 C7 C8 -18.9(2) . . . . ?
C6 C5 C10 C1 178.62(13) . . . . ?
C6 C5 C10 C9 -61.68(16) . . . . ?
C6 C5 C10 C20 55.53(18) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C6 C7 C8 C14 177.08(15) . . . . ?
C7 C8 C9 C10 -12.7(2) . . . . ?
C7 C8 C9 C11 169.15(17) . . . . ?
C7 C8 C14 O2 98.01(18) . . . . ?
C7 C8 C14 C13 -144.45(15) . . . . ?
C8 C9 C10 C1 161.55(16) . . . . ?
C8 C9 C10 C5 42.92(19) . . . . ?
C8 C9 C10 C20 -78.94(18) . . . . ?
C8 C9 C11 C12 1.0(3) . . . . ?
C9 C8 C14 O2 -84.03(18) . . . . ?
C9 C8 C14 C13 33.5(2) . . . . ?
C9 C11 C12 C13 -18.2(3) . . . . ?
C10 C1 C2 C3 59.8(2) . . . . ?
C10 C5 C6 C7 50.60(17) . . . . ?
C10 C9 C11 C12 -176.96(17) . . . . ?
C11 C9 C10 C1 -20.4(3) . . . . ?
C11 C9 C10 C5 -139.02(18) . . . . ?
C11 C9 C10 C20 99.1(2) . . . . ?
C11 C12 C13 C14 40.4(2) . . . . ?
C11 C12 C13 C15 149.57(15) . . . . ?
C11 C12 C13 C17 -84.41(19) . . . . ?
C12 C13 C14 O2 73.34(16) . . . . ?
C12 C13 C14 C8 -48.11(19) . . . . ?
C12 C13 C15 O3 165.88(13) . . . . ?
C12 C13 C15 C16 -77.56(17) . . . . ?
C13 C15 C16 O2 -22.61(19) . . . . ?
C14 O2 C16 C15 -3.29(19) . . . . ?
C14 C8 C9 C10 169.37(14) . . . . ?
C14 C8 C9 C11 -8.8(2) . . . . ?
C14 C13 C15 O3 -78.43(16) . . . . ?
C14 C13 C15 C16 38.13(17) . . . . ?
C15 C13 C14 O2 -41.27(16) . . . . ?
C15 C13 C14 C8 -162.72(14) . . . . ?
C16 O2 C14 C8 151.95(14) . . . . ?
C16 O2 C14 C13 28.29(17) . . . . ?
C17 C13 C14 O2 -163.20(14) . . . . ?
C17 C13 C14 C8 75.35(19) . . . . ?
C17 C13 C15 O3 42.2(2) . . . . ?
C17 C13 C15 C16 158.80(15) . . . . ?
C18 C4 C5 C6 65.42(18) . . . . ?
C18 C4 C5 C10 -164.38(15) . . . . ?
C19 C4 C5 C6 -54.91(19) . . . . ?
C19 C4 C5 C10 75.29(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.736
_oxdiff_exptl_absorpt_empirical_full_min 0.657
####################################################################### 
# 
# 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_xjy-53
_database_code_depnum_ccdc_archive 'CCDC 2453118'
loop_
_audit_author_name
_audit_author_address
'Sheng Lin'
;Beijing University of Chinese Medicine
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-11
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H34 O4'
_chemical_formula_sum            'C20 H34 O4'
_chemical_formula_weight         338.47
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.3800(4)
_cell_length_b                   12.1066(4)
_cell_length_c                   20.3919(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1821.95(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10603
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7820
_cell_measurement_theta_min      4.2230
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1125
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20517
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.161
_diffrn_reflns_theta_min         4.247
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00 115.00   1.00    1.00    --   40.92  37.00 120.00   98
  2  ω    -31.00  69.00   1.00    1.00    --   40.92 -57.00  60.00  100
  3  ω     13.00 113.00   1.00    1.00    --   40.92  57.00-150.00  100
  4  ω     94.00 178.00   1.00    2.15    --  107.58 125.00 120.00   84
  5  ω     25.00 109.00   1.00    2.15    --  107.58 -94.00-150.00   84
  6  ω     35.00 133.00   1.00    2.15    --  107.58 -45.00   0.00   98
  7  ω     82.00 178.00   1.00    2.15    --  107.58  45.00-120.00   96
  8  ω     75.00 178.00   1.00    2.15    --  107.58  77.00 150.00  103
  9  ω     13.00 113.00   1.00    1.00    --   40.92  57.00   0.00  100
 10  ω     23.00  97.00   1.00    1.00    --   40.92-125.00 -30.00   74
 11  ω     55.00 178.00   1.00    2.15    --  107.58  15.00  90.00  123
 12  ω     35.00 133.00   1.00    2.15    --  107.58 -45.00-180.00   98
 13  ω     34.00 122.00   1.00    2.15    --  107.58-125.00-180.00   88
 14  ω     79.00 178.00   1.00    2.15    --  107.58  30.00 -30.00   99
 15  ω    -69.00  32.00   1.00    1.00    --  -40.92  57.00-120.00  101
 16  ω     13.00 113.00   1.00    1.00    --   40.92  57.00 -90.00  100
 17  ω     82.00 178.00   1.00    2.15    --  107.58  45.00 120.00   96
 18  ω     75.00 178.00   1.00    2.15    --  107.58  77.00 -30.00  103
 19  ω     78.00 160.00   1.00    2.15    --  107.58  61.00 -90.00   82
 20  ω     82.00 178.00   1.00    2.15    --  107.58  45.00-150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0936599000
_diffrn_orient_matrix_UB_12      0.1039723000
_diffrn_orient_matrix_UB_13      0.0273492000
_diffrn_orient_matrix_UB_21      0.0568770000
_diffrn_orient_matrix_UB_22      -0.0649646000
_diffrn_orient_matrix_UB_23      0.0615940000
_diffrn_orient_matrix_UB_31      0.1777677000
_diffrn_orient_matrix_UB_32      -0.0339142000
_diffrn_orient_matrix_UB_33      -0.0341271000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3361
_reflns_number_total             3654
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 1226 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     255
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0765
_refine_ls_restrained_S_all      1.040
_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)+(0.1251P)²+2.0777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2042
_refine_ls_wR_factor_ref         0.2114
_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 C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C14) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.0005 and sigma
for terminal atoms of 0.001
Uanis(O4) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.00006 and sigma for
terminal atoms of 0.00012
3. Rigid body (RIGU) restrains
 O1, H1, O2, H2, O3, H3, O4, H4, C1, H1A, H1B, C2, H2A, H2B, C3, H3A, C4, C5,
 H5, C6, H6, C7, H7A, H7B, C8, C9, H9, C10, C11, H11A, H11B, C12, H12A, H12B,
 C13, C14, H14, C15, H15, C16, H16A, H16B, C17, H17A, H17B, H17C, C18, H18A,
 H18B, H18C, C19, H19A, H19B, H19C, C20, H20A, H20B, H20C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Ternary CH refined with riding coordinates:
 C3(H3A), C5(H5), C6(H6), C9(H9), C15(H15)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B),
 C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C14(H14)
4.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.4723(5) 0.2384(2) 0.17744(15) 0.0240(7) Uani 1 1 d . . . . .
H1 H 0.428113 0.176795 0.167336 0.036 Uiso 1 1 calc R U . . .
O2 O 0.7114(5) 0.5443(2) 0.36268(16) 0.0232(7) Uani 1 1 d . . . . .
H2 H 0.766949 0.581592 0.391027 0.035 Uiso 1 1 calc R U . . .
O3 O 0.0985(5) 0.6385(3) 0.56474(16) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.095170 0.675438 0.599606 0.038 Uiso 1 1 calc R U . . .
O4 O 0.3477(5) 0.8216(3) 0.53478(17) 0.0305(8) Uani 1 1 d . U . . .
H4 H 0.414625 0.833387 0.502210 0.046 Uiso 1 1 calc R U . . .
C1 C 0.2714(6) 0.2872(3) 0.3448(2) 0.0202(8) Uani 1 1 d . . . . .
H1A H 0.307223 0.215599 0.364420 0.024 Uiso 1 1 calc R U . . .
H1B H 0.145327 0.302995 0.358547 0.024 Uiso 1 1 calc R U . . .
C2 C 0.2784(6) 0.2778(3) 0.2704(2) 0.0219(8) Uani 1 1 d . . . . .
H2A H 0.194769 0.218833 0.255681 0.026 Uiso 1 1 calc R U . . .
H2B H 0.238180 0.348246 0.250479 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4682(6) 0.2516(3) 0.2477(2) 0.0196(8) Uani 1 1 d . . . . .
H3A H 0.503181 0.179095 0.267561 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6118(6) 0.3369(3) 0.26839(19) 0.0167(8) Uani 1 1 d . U . . .
C5 C 0.5909(6) 0.3552(3) 0.34398(19) 0.0161(7) Uani 1 1 d . U . . .
H5 H 0.618928 0.280518 0.362367 0.019 Uiso 1 1 calc R U . . .
C6 C 0.7371(6) 0.4288(3) 0.37553(18) 0.0155(7) Uani 1 1 d . U . . .
H6 H 0.857491 0.406544 0.357294 0.019 Uiso 1 1 calc R U . . .
C7 C 0.7401(6) 0.4087(3) 0.44950(19) 0.0162(7) Uani 1 1 d . U . . .
H7A H 0.777711 0.331652 0.458286 0.019 Uiso 1 1 calc R U . . .
H7B H 0.830064 0.458522 0.470105 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5567(6) 0.4290(3) 0.47935(19) 0.0165(7) Uani 1 1 d . U . . .
C9 C 0.4023(6) 0.3656(3) 0.4478(2) 0.0174(7) Uani 1 1 d . . . . .
H9 H 0.426519 0.285708 0.456469 0.021 Uiso 1 1 calc R U . . .
C10 C 0.3972(6) 0.3788(3) 0.3712(2) 0.0161(7) Uani 1 1 d . . . . .
C11 C 0.2193(6) 0.3917(3) 0.4803(2) 0.0215(9) Uani 1 1 d . . . . .
H11A H 0.164918 0.456704 0.458366 0.026 Uiso 1 1 calc R U . . .
H11B H 0.136532 0.328302 0.473716 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2355(7) 0.4151(3) 0.5533(2) 0.0231(9) Uani 1 1 d . . . . .
H12A H 0.280167 0.347961 0.575785 0.028 Uiso 1 1 calc R U . . .
H12B H 0.113854 0.432347 0.571057 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3643(7) 0.5119(3) 0.5685(2) 0.0193(8) Uani 1 1 d . . . . .
C14 C 0.5391(6) 0.4922(4) 0.5325(2) 0.0195(8) Uani 1 1 d . U . . .
H14 H 0.644874 0.527403 0.548898 0.023 Uiso 1 1 calc R U . . .
C15 C 0.2820(7) 0.6238(3) 0.5451(2) 0.0223(8) Uani 1 1 d . . . . .
H15 H 0.282445 0.622140 0.496048 0.027 Uiso 1 1 calc R U . . .
C16 C 0.4005(7) 0.7215(4) 0.5656(2) 0.0260(9) Uani 1 1 d . U . . .
H16A H 0.393032 0.730748 0.613776 0.031 Uiso 1 1 calc R U . . .
H16B H 0.528205 0.705288 0.554304 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4022(8) 0.5126(4) 0.6425(2) 0.0264(10) Uani 1 1 d . . . . .
H17A H 0.457734 0.442296 0.655344 0.040 Uiso 1 1 calc R U . . .
H17B H 0.288118 0.522503 0.666445 0.040 Uiso 1 1 calc R U . . .
H17C H 0.484820 0.573393 0.653092 0.040 Uiso 1 1 calc R U . . .
C18 C 0.7979(6) 0.2856(4) 0.2548(2) 0.0242(9) Uani 1 1 d . . . . .
H18A H 0.892630 0.340862 0.262412 0.036 Uiso 1 1 calc R U . . .
H18B H 0.803249 0.260650 0.209076 0.036 Uiso 1 1 calc R U . . .
H18C H 0.816875 0.222488 0.284051 0.036 Uiso 1 1 calc R U . . .
C19 C 0.5999(7) 0.4420(3) 0.2259(2) 0.0215(9) Uani 1 1 d . . . . .
H19A H 0.475846 0.470856 0.227174 0.032 Uiso 1 1 calc R U . . .
H19B H 0.632604 0.424081 0.180600 0.032 Uiso 1 1 calc R U . . .
H19C H 0.683538 0.497841 0.243062 0.032 Uiso 1 1 calc R U . . .
C20 C 0.3198(7) 0.4930(3) 0.3527(2) 0.0212(9) Uani 1 1 d . . . . .
H20A H 0.364651 0.548645 0.383615 0.032 Uiso 1 1 calc R U . . .
H20B H 0.187150 0.490577 0.354568 0.032 Uiso 1 1 calc R U . . .
H20C H 0.358367 0.512382 0.308181 0.032 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 H1 0.8400 . ?
O1 C3 1.442(5) . ?
O2 H2 0.8400 . ?
O2 C6 1.436(5) . ?
O3 H3 0.8400 . ?
O3 C15 1.423(6) . ?
O4 H4 0.8400 . ?
O4 C16 1.420(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.524(6) . ?
C1 C10 1.544(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.509(7) . ?
C3 H3A 1.0000 . ?
C3 C4 1.539(6) . ?
C4 C5 1.565(5) . ?
C4 C18 1.533(6) . ?
C4 C19 1.541(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.540(6) . ?
C5 C10 1.560(6) . ?
C6 H6 1.0000 . ?
C6 C7 1.528(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.504(6) . ?
C8 C9 1.517(6) . ?
C8 C14 1.334(6) . ?
C9 H9 1.0000 . ?
C9 C10 1.569(5) . ?
C9 C11 1.537(6) . ?
C10 C20 1.543(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.521(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.540(6) . ?
C13 C14 1.503(6) . ?
C13 C15 1.560(6) . ?
C13 C17 1.535(6) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.529(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C3 O1 H1 109.5 . . ?
C6 O2 H2 109.5 . . ?
C15 O3 H3 109.5 . . ?
C16 O4 H4 109.5 . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C2 C1 C10 112.4(3) . . ?
C10 C1 H1A 109.1 . . ?
C10 C1 H1B 109.1 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.6(4) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
O1 C3 C2 110.3(4) . . ?
O1 C3 H3A 107.5 . . ?
O1 C3 C4 109.4(3) . . ?
C2 C3 H3A 107.5 . . ?
C2 C3 C4 114.4(3) . . ?
C4 C3 H3A 107.5 . . ?
C3 C4 C5 107.3(3) . . ?
C3 C4 C19 111.2(3) . . ?
C18 C4 C3 107.1(3) . . ?
C18 C4 C5 108.9(3) . . ?
C18 C4 C19 106.5(3) . . ?
C19 C4 C5 115.6(3) . . ?
C4 C5 H5 102.8 . . ?
C6 C5 C4 115.1(3) . . ?
C6 C5 H5 102.8 . . ?
C6 C5 C10 112.8(3) . . ?
C10 C5 C4 117.8(3) . . ?
C10 C5 H5 102.8 . . ?
O2 C6 C5 113.3(3) . . ?
O2 C6 H6 108.1 . . ?
O2 C6 C7 109.7(3) . . ?
C5 C6 H6 108.1 . . ?
C7 C6 C5 109.3(3) . . ?
C7 C6 H6 108.1 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 C9 115.0(3) . . ?
C14 C8 C7 120.7(4) . . ?
C14 C8 C9 124.2(4) . . ?
C8 C9 H9 106.2 . . ?
C8 C9 C10 112.9(3) . . ?
C8 C9 C11 111.9(3) . . ?
C10 C9 H9 106.2 . . ?
C11 C9 H9 106.2 . . ?
C11 C9 C10 112.8(3) . . ?
C1 C10 C5 107.2(3) . . ?
C1 C10 C9 106.7(3) . . ?
C5 C10 C9 108.3(3) . . ?
C20 C10 C1 109.6(3) . . ?
C20 C10 C5 114.6(3) . . ?
C20 C10 C9 110.1(3) . . ?
C9 C11 H11A 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C9 113.1(4) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C11 C12 C13 112.8(3) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 C15 111.0(4) . . ?
C14 C13 C12 108.1(3) . . ?
C14 C13 C15 108.8(3) . . ?
C14 C13 C17 108.9(4) . . ?
C17 C13 C12 108.3(4) . . ?
C17 C13 C15 111.6(3) . . ?
C8 C14 C13 124.9(4) . . ?
C8 C14 H14 117.6 . . ?
C13 C14 H14 117.6 . . ?
O3 C15 C13 113.1(4) . . ?
O3 C15 H15 106.7 . . ?
O3 C15 C16 111.7(3) . . ?
C13 C15 H15 106.7 . . ?
C16 C15 C13 111.4(4) . . ?
C16 C15 H15 106.7 . . ?
O4 C16 C15 112.5(4) . . ?
O4 C16 H16A 109.1 . . ?
O4 C16 H16B 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C3 C4 C5 175.4(3) . . . . ?
O1 C3 C4 C18 -67.7(4) . . . . ?
O1 C3 C4 C19 48.2(4) . . . . ?
O2 C6 C7 C8 68.3(4) . . . . ?
O3 C15 C16 O4 -63.4(5) . . . . ?
C1 C2 C3 O1 177.7(3) . . . . ?
C1 C2 C3 C4 -58.5(5) . . . . ?
C2 C1 C10 C5 -54.6(4) . . . . ?
C2 C1 C10 C9 -170.4(3) . . . . ?
C2 C1 C10 C20 70.4(4) . . . . ?
C2 C3 C4 C5 51.1(5) . . . . ?
C2 C3 C4 C18 167.9(4) . . . . ?
C2 C3 C4 C19 -76.1(4) . . . . ?
C3 C4 C5 C6 173.6(3) . . . . ?
C3 C4 C5 C10 -49.5(5) . . . . ?
C4 C5 C6 O2 76.3(4) . . . . ?
C4 C5 C6 C7 -161.1(3) . . . . ?
C4 C5 C10 C1 51.7(4) . . . . ?
C4 C5 C10 C9 166.5(3) . . . . ?
C4 C5 C10 C20 -70.2(5) . . . . ?
C5 C6 C7 C8 -56.5(4) . . . . ?
C6 C5 C10 C1 -170.4(3) . . . . ?
C6 C5 C10 C9 -55.6(4) . . . . ?
C6 C5 C10 C20 67.7(4) . . . . ?
C6 C7 C8 C9 53.6(5) . . . . ?
C6 C7 C8 C14 -131.0(4) . . . . ?
C7 C8 C9 C10 -50.8(4) . . . . ?
C7 C8 C9 C11 -179.3(3) . . . . ?
C7 C8 C14 C13 -176.0(4) . . . . ?
C8 C9 C10 C1 164.7(3) . . . . ?
C8 C9 C10 C5 49.7(4) . . . . ?
C8 C9 C10 C20 -76.3(4) . . . . ?
C8 C9 C11 C12 -33.1(5) . . . . ?
C9 C8 C14 C13 -1.1(7) . . . . ?
C9 C11 C12 C13 57.9(5) . . . . ?
C10 C1 C2 C3 59.9(4) . . . . ?
C10 C5 C6 O2 -62.8(4) . . . . ?
C10 C5 C6 C7 59.9(4) . . . . ?
C10 C9 C11 C12 -161.7(3) . . . . ?
C11 C9 C10 C1 -67.2(4) . . . . ?
C11 C9 C10 C5 177.7(3) . . . . ?
C11 C9 C10 C20 51.7(4) . . . . ?
C11 C12 C13 C14 -50.2(5) . . . . ?
C11 C12 C13 C15 69.1(5) . . . . ?
C11 C12 C13 C17 -168.1(4) . . . . ?
C12 C13 C14 C8 23.0(6) . . . . ?
C12 C13 C15 O3 47.9(5) . . . . ?
C12 C13 C15 C16 174.7(4) . . . . ?
C13 C15 C16 O4 169.0(4) . . . . ?
C14 C8 C9 C10 134.0(4) . . . . ?
C14 C8 C9 C11 5.5(6) . . . . ?
C14 C13 C15 O3 166.7(4) . . . . ?
C14 C13 C15 C16 -66.4(4) . . . . ?
C15 C13 C14 C8 -97.6(5) . . . . ?
C17 C13 C14 C8 140.6(4) . . . . ?
C17 C13 C15 O3 -73.1(5) . . . . ?
C17 C13 C15 C16 53.8(5) . . . . ?
C18 C4 C5 C6 57.9(4) . . . . ?
C18 C4 C5 C10 -165.1(3) . . . . ?
C19 C4 C5 C6 -61.8(5) . . . . ?
C19 C4 C5 C10 75.1(5) . . . . ?

_olex2_date_sample_data_collection 2023-01-10
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.556
_oxdiff_exptl_absorpt_empirical_full_min 0.246
####################################################################### 
# 
# 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_57-1
_database_code_depnum_ccdc_archive 'CCDC 2453134'
loop_
_audit_author_name
_audit_author_address
'Sheng Lin'
;Beijing University of Chinese Medicine
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-11
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H34 O3'
_chemical_formula_sum            'C20 H34 O3'
_chemical_formula_weight         322.47
_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      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                   11.2450(3)
_cell_length_b                   7.2402(2)
_cell_length_c                   11.5790(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.615(3)
_cell_angle_gamma                90
_cell_volume                     929.48(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5494
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.7280
_cell_measurement_theta_min      3.8390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7872
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.780
_diffrn_reflns_theta_min         3.872
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  82.00   1.00    1.00    --   40.92 -99.00   0.00   46
  2  ω     43.00  69.00   1.00    1.00    --  107.58-112.00 -20.00   26
  3  ω     64.00 136.00   1.00    1.00    --  107.58 -30.00 -60.00   72
  4  ω     82.00 178.00   1.00    1.00    --  107.58  45.00 -60.00   96
  5  ω    121.00 178.00   1.00    1.00    --  107.58 125.00-150.00   57
  6  ω     42.00 133.00   1.00    1.00    --  107.58 -30.00 120.00   91
  7  ω     35.00 103.00   1.00    1.00    --  107.58 -94.00 150.00   68
  8  ω    -64.00  31.00   1.00    1.00    --  -40.92  37.00-150.00   95
  9  ω   -109.00 -16.00   1.00    1.00    --  -40.92 -57.00-120.00   93
 10  ω    -47.00 -20.00   1.00    1.00    --  -41.23 -37.00  60.00   27
 11  ω   -101.00 -18.00   1.00    1.00    --  -41.23 -57.00   0.00   83
 12  ω    -42.00 -12.00   1.00    1.00    --  -41.23 -77.00  60.00   30
 13  ω     37.00  66.00   1.00    1.00    --   41.23-125.00 -60.00   29
 14  ω     78.00 104.00   1.00    1.00    --  107.58  77.00 120.00   26
 15  ω     75.00 100.00   1.00    1.00    --  107.58  77.00  60.00   25
 16  ω     78.00 116.00   1.00    1.00    --  107.58  61.00  60.00   38
 17  ω    111.00 137.00   1.00    1.00    --  107.58  61.00  30.00   26
 18  ω     76.00 102.00   1.00    1.00    --  107.58  77.00   0.00   26
 19  ω     78.00 104.00   1.00    1.00    --  107.58  61.00  90.00   26
 20  ω     81.00 107.00   1.00    1.00    --  107.58  61.00 120.00   26
 21  ω     79.00 110.00   1.00    1.00    --  107.58  61.00  30.00   31
 22  ω     75.00 119.00   1.00    1.00    --  107.58  77.00  30.00   44
 23  ω     78.00 137.00   1.00    1.00    --  107.58  61.00   0.00   59
 24  ω     85.00 116.00   1.00    1.00    --  107.58  45.00  30.00   31
 25  ω     75.00 101.00   1.00    1.00    --  107.58  77.00  90.00   26
 26  ω     83.00 117.00   1.00    1.00    --  107.58  45.00 150.00   34
 27  ω    132.00 174.00   1.00    1.00    --  107.58  61.00  60.00   42
 28  ω     78.00 123.00   1.00    1.00    --  107.58  61.00 150.00   45
 29  ω     99.00 124.00   1.00    1.00    --  107.58 125.00-150.00   25
 30  ω     83.00 108.00   1.00    1.00    --  107.58  45.00  90.00   25
 31  ω     84.00 110.00   1.00    1.00    --  107.58  30.00 120.00   26
 32  ω     85.00 111.00   1.00    1.00    --  107.58  45.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0820977000
_diffrn_orient_matrix_UB_12      -0.0181945000
_diffrn_orient_matrix_UB_13      -0.1201067000
_diffrn_orient_matrix_UB_21      0.1100890000
_diffrn_orient_matrix_UB_22      -0.0540176000
_diffrn_orient_matrix_UB_23      -0.0560617000
_diffrn_orient_matrix_UB_31      -0.0216576000
_diffrn_orient_matrix_UB_32      -0.2048558000
_diffrn_orient_matrix_UB_33      0.0254277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                3384
_reflns_number_total             3472
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.063
_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)+(0.0499P)²+0.0737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0859
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.45607(12) 0.21159(19) 0.77904(11) 0.0291(3) Uani 1 1 d . . . . .
O2 O 0.35296(13) 0.8795(2) 0.79749(11) 0.0331(3) Uani 1 1 d . . . . .
H2 H 0.383369 0.984120 0.790676 0.050 Uiso 1 1 calc R U . . .
O3 O 0.48800(13) 0.2777(2) 0.00849(12) 0.0349(3) Uani 1 1 d . . . . .
C1 C 0.33845(15) 0.2768(3) 0.59358(14) 0.0227(3) Uani 1 1 d . . . . .
H1A H 0.273345 0.194378 0.610767 0.027 Uiso 1 1 calc R U . . .
H1B H 0.396600 0.200421 0.559077 0.027 Uiso 1 1 calc R U . . .
C2 C 0.40215(15) 0.3604(3) 0.70710(14) 0.0228(3) Uani 1 1 d . . . . .
H2A H 0.466791 0.446010 0.690017 0.027 Uiso 1 1 calc R U . . .
C3 C 0.31170(16) 0.4682(3) 0.76510(15) 0.0237(4) Uani 1 1 d . . . . .
H3A H 0.354193 0.522592 0.839044 0.028 Uiso 1 1 calc R U . . .
H3B H 0.250121 0.381596 0.785171 0.028 Uiso 1 1 calc R U . . .
C4 C 0.24787(15) 0.6238(3) 0.68745(14) 0.0225(3) Uani 1 1 d . . . . .
C5 C 0.19883(14) 0.5493(2) 0.56189(14) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.129236 0.468505 0.572109 0.026 Uiso 1 1 calc R U . . .
C6 C 0.14430(16) 0.6973(3) 0.47395(15) 0.0266(4) Uani 1 1 d . . . . .
H6A H 0.090351 0.778111 0.510881 0.032 Uiso 1 1 calc R U . . .
H6B H 0.209727 0.774751 0.452328 0.032 Uiso 1 1 calc R U . . .
C7 C 0.07297(16) 0.6098(3) 0.36366(16) 0.0291(4) Uani 1 1 d . . . . .
H7A H -0.002699 0.557359 0.382768 0.035 Uiso 1 1 calc R U . . .
H7B H 0.050824 0.707360 0.304032 0.035 Uiso 1 1 calc R U . . .
C8 C 0.14114(15) 0.4591(3) 0.31185(15) 0.0251(4) Uani 1 1 d . . . . .
C9 C 0.20440(15) 0.3204(2) 0.39921(14) 0.0221(4) Uani 1 1 d . . . . .
H9 H 0.140033 0.253209 0.432289 0.026 Uiso 1 1 calc R U . . .
C10 C 0.28415(14) 0.4217(2) 0.50395(14) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.27444(17) 0.1741(3) 0.34087(15) 0.0263(4) Uani 1 1 d . . . . .
H11A H 0.355256 0.222880 0.334222 0.032 Uiso 1 1 calc R U . . .
H11B H 0.285594 0.062188 0.390667 0.032 Uiso 1 1 calc R U . . .
C12 C 0.20783(17) 0.1223(3) 0.21930(16) 0.0302(4) Uani 1 1 d . . . . .
H12A H 0.127010 0.073634 0.226052 0.036 Uiso 1 1 calc R U . . .
H12B H 0.252824 0.023412 0.186255 0.036 Uiso 1 1 calc R U . . .
C13 C 0.19387(17) 0.2880(3) 0.13626(15) 0.0297(4) Uani 1 1 d . . . . .
C14 C 0.14029(17) 0.4463(3) 0.19673(16) 0.0300(4) Uani 1 1 d . . . . .
H14 H 0.103244 0.543784 0.148835 0.036 Uiso 1 1 calc R U . . .
C15 C 0.31563(17) 0.3521(3) 0.10344(16) 0.0306(4) Uani 1 1 d . . . . .
H15A H 0.299673 0.455413 0.046972 0.037 Uiso 1 1 calc R U . . .
H15B H 0.367088 0.400345 0.174822 0.037 Uiso 1 1 calc R U . . .
C16 C 0.38533(17) 0.2035(3) 0.05054(17) 0.0345(4) Uani 1 1 d . . . . .
H16A H 0.412362 0.108169 0.110477 0.041 Uiso 1 1 calc R U . . .
H16B H 0.331421 0.143355 -0.015041 0.041 Uiso 1 1 calc R U . . .
C17 C 0.10517(19) 0.2392(4) 0.02434(18) 0.0431(6) Uani 1 1 d . . . . .
H17A H 0.025555 0.213315 0.044433 0.065 Uiso 1 1 calc R U . . .
H17B H 0.134336 0.129872 -0.012290 0.065 Uiso 1 1 calc R U . . .
H17C H 0.099130 0.343309 -0.030419 0.065 Uiso 1 1 calc R U . . .
C18 C 0.13983(18) 0.6858(3) 0.74400(17) 0.0342(5) Uani 1 1 d . . . . .
H18A H 0.104499 0.797905 0.704981 0.051 Uiso 1 1 calc R U . . .
H18B H 0.167202 0.711487 0.827300 0.051 Uiso 1 1 calc R U . . .
H18C H 0.079052 0.587590 0.735697 0.051 Uiso 1 1 calc R U . . .
C19 C 0.33308(18) 0.7890(3) 0.68609(15) 0.0282(4) Uani 1 1 d . . . . .
H19A H 0.411084 0.745780 0.667083 0.034 Uiso 1 1 calc R U . . .
H19B H 0.297597 0.877432 0.624701 0.034 Uiso 1 1 calc R U . . .
C20 C 0.38521(15) 0.5288(3) 0.45820(15) 0.0251(4) Uani 1 1 d . . . . .
H20A H 0.352080 0.590188 0.384375 0.038 Uiso 1 1 calc R U . . .
H20B H 0.448881 0.442825 0.445023 0.038 Uiso 1 1 calc R U . . .
H20C H 0.418918 0.621693 0.516121 0.038 Uiso 1 1 calc R U . . .
H3 H 0.553(3) 0.307(5) 0.068(3) 0.075(10) Uiso 1 1 d . . . . .
H1 H 0.478(3) 0.250(5) 0.852(3) 0.076(10) Uiso 1 1 d . . . . .


_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 C2 1.433(2) . ?
O1 H1 0.89(3) . ?
O2 H2 0.8400 . ?
O2 C19 1.431(2) . ?
O3 C16 1.431(2) . ?
O3 H3 0.94(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.514(2) . ?
C1 C10 1.529(2) . ?
C2 H2A 1.0000 . ?
C2 C3 1.524(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.542(2) . ?
C4 C5 1.562(2) . ?
C4 C18 1.540(2) . ?
C4 C19 1.534(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.533(2) . ?
C5 C10 1.562(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.514(3) . ?
C8 C9 1.515(2) . ?
C8 C14 1.335(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.565(2) . ?
C9 C11 1.542(2) . ?
C10 C20 1.541(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.527(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.529(3) . ?
C13 C14 1.519(3) . ?
C13 C15 1.552(3) . ?
C13 C17 1.539(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C2 O1 H1 110(2) . . ?
C19 O2 H2 109.5 . . ?
C16 O3 H3 114(2) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C2 C1 C10 113.10(15) . . ?
C10 C1 H1A 109.0 . . ?
C10 C1 H1B 109.0 . . ?
O1 C2 C1 107.28(14) . . ?
O1 C2 H2A 109.3 . . ?
O1 C2 C3 112.18(13) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 C3 109.47(14) . . ?
C3 C2 H2A 109.3 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.40(13) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 C5 110.37(14) . . ?
C18 C4 C3 106.78(14) . . ?
C18 C4 C5 108.38(14) . . ?
C19 C4 C3 110.18(14) . . ?
C19 C4 C5 112.55(14) . . ?
C19 C4 C18 108.38(15) . . ?
C4 C5 H5 104.7 . . ?
C6 C5 C4 114.63(15) . . ?
C6 C5 H5 104.7 . . ?
C6 C5 C10 109.54(13) . . ?
C10 C5 C4 117.21(13) . . ?
C10 C5 H5 104.7 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.19(16) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.59(15) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C7 C8 C9 115.18(14) . . ?
C14 C8 C7 121.74(17) . . ?
C14 C8 C9 123.01(17) . . ?
C8 C9 H9 106.8 . . ?
C8 C9 C10 110.56(14) . . ?
C8 C9 C11 112.33(14) . . ?
C10 C9 H9 106.8 . . ?
C11 C9 H9 106.8 . . ?
C11 C9 C10 113.14(14) . . ?
C1 C10 C5 108.59(12) . . ?
C1 C10 C9 108.47(14) . . ?
C1 C10 C20 110.18(13) . . ?
C5 C10 C9 107.25(12) . . ?
C20 C10 C5 112.99(14) . . ?
C20 C10 C9 109.24(12) . . ?
C9 C11 H11A 109.4 . . ?
C9 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C9 111.39(15) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C11 C12 C13 111.74(16) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 C15 112.74(16) . . ?
C12 C13 C17 109.47(18) . . ?
C14 C13 C12 107.99(14) . . ?
C14 C13 C15 108.76(16) . . ?
C14 C13 C17 108.08(17) . . ?
C17 C13 C15 109.68(15) . . ?
C8 C14 C13 125.14(18) . . ?
C8 C14 H14 117.4 . . ?
C13 C14 H14 117.4 . . ?
C13 C15 H15A 108.5 . . ?
C13 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 C13 115.01(17) . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
O3 C16 C15 111.79(18) . . ?
O3 C16 H16A 109.3 . . ?
O3 C16 H16B 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 C4 110.60(14) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C2 C3 C4 -177.39(15) . . . . ?
C1 C2 C3 C4 -58.4(2) . . . . ?
C2 C1 C10 C5 -55.09(17) . . . . ?
C2 C1 C10 C9 -171.33(13) . . . . ?
C2 C1 C10 C20 69.15(16) . . . . ?
C2 C3 C4 C5 48.76(19) . . . . ?
C2 C3 C4 C18 166.36(15) . . . . ?
C2 C3 C4 C19 -76.14(18) . . . . ?
C3 C4 C5 C6 -174.40(14) . . . . ?
C3 C4 C5 C10 -43.91(19) . . . . ?
C3 C4 C19 O2 -70.07(18) . . . . ?
C4 C5 C6 C7 -166.73(14) . . . . ?
C4 C5 C10 C1 46.57(19) . . . . ?
C4 C5 C10 C9 163.59(14) . . . . ?
C4 C5 C10 C20 -75.98(18) . . . . ?
C5 C4 C19 O2 166.28(14) . . . . ?
C5 C6 C7 C8 -49.2(2) . . . . ?
C6 C5 C10 C1 179.39(14) . . . . ?
C6 C5 C10 C9 -63.59(16) . . . . ?
C6 C5 C10 C20 56.84(17) . . . . ?
C6 C7 C8 C9 46.0(2) . . . . ?
C6 C7 C8 C14 -136.84(19) . . . . ?
C7 C8 C9 C10 -51.14(19) . . . . ?
C7 C8 C9 C11 -178.58(15) . . . . ?
C7 C8 C14 C13 -172.65(17) . . . . ?
C8 C9 C10 C1 175.91(12) . . . . ?
C8 C9 C10 C5 58.81(16) . . . . ?
C8 C9 C10 C20 -63.98(17) . . . . ?
C8 C9 C11 C12 -36.2(2) . . . . ?
C9 C8 C14 C13 4.3(3) . . . . ?
C9 C11 C12 C13 62.07(19) . . . . ?
C10 C1 C2 O1 -175.74(13) . . . . ?
C10 C1 C2 C3 62.29(17) . . . . ?
C10 C5 C6 C7 59.13(18) . . . . ?
C10 C9 C11 C12 -162.27(14) . . . . ?
C11 C9 C10 C1 -57.10(17) . . . . ?
C11 C9 C10 C5 -174.20(14) . . . . ?
C11 C9 C10 C20 63.02(18) . . . . ?
C11 C12 C13 C14 -51.2(2) . . . . ?
C11 C12 C13 C15 68.94(19) . . . . ?
C11 C12 C13 C17 -168.68(15) . . . . ?
C12 C13 C14 C8 19.3(3) . . . . ?
C12 C13 C15 C16 55.7(2) . . . . ?
C13 C15 C16 O3 172.31(15) . . . . ?
C14 C8 C9 C10 131.75(18) . . . . ?
C14 C8 C9 C11 4.3(2) . . . . ?
C14 C13 C15 C16 175.42(16) . . . . ?
C15 C13 C14 C8 -103.4(2) . . . . ?
C17 C13 C14 C8 137.6(2) . . . . ?
C17 C13 C15 C16 -66.6(2) . . . . ?
C18 C4 C5 C6 69.00(18) . . . . ?
C18 C4 C5 C10 -160.51(15) . . . . ?
C18 C4 C19 O2 46.43(19) . . . . ?
C19 C4 C5 C6 -50.86(18) . . . . ?
C19 C4 C5 C10 79.63(19) . . . . ?

_olex2_date_sample_data_collection 2023-01-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.678
