# 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_jk63392
_database_code_depnum_ccdc_archive 'CCDC 2527269'
loop_
_audit_author_name
_audit_author_address
'WU YING'
;Kunming Institute of Botany,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2026-01-30 deposited with the CCDC.	2026-03-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H20 O6'
_chemical_formula_sum            'C19 H20 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         344.35
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   10.4759(2)
_cell_length_b                   5.47890(10)
_cell_length_c                   15.0364(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.2890(10)
_cell_angle_gamma                90
_cell_volume                     836.34(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      3.0328
_cell_measurement_theta_max      69.9376
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364

_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            14587
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_full        69.93
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3103
_reflns_number_gt                2937
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0964
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         3103
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.1478P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.23(10)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2911(2) 0.8227(4) 0.67837(13) 0.0597(5) Uani d . . . 1 . .
O O2 0.92137(17) 0.7984(4) 0.55339(12) 0.0526(5) Uani d . . . 1 . .
O O3 0.16141(19) 0.7961(5) 0.78224(15) 0.0636(6) Uani d . . . 1 . .
O O4 0.70949(17) 0.7859(4) 0.45928(12) 0.0521(5) Uani d . . . 1 . .
O O5 0.8936(2) 0.0444(4) 0.91257(16) 0.0718(7) Uani d . . . 1 . .
H H17 0.969724 0.072802 0.945024 0.108 Uiso calc U . R 1 . .
C C1 0.1938(3) 0.9482(6) 0.7128(2) 0.0602(8) Uani d . . . 1 . .
H H3 0.114389 0.978518 0.662602 0.072 Uiso calc U . R 1 . .
H H1 0.228672 1.107194 0.73942 0.072 Uiso calc U . R 1 . .
C C2 0.3443(3) 0.6570(5) 0.74621(16) 0.0454(6) Uani d . . . 1 . .
C C3 0.4538(2) 0.5156(5) 0.75257(15) 0.0425(6) Uani d . . . 1 . .
H H4 0.504902 0.527633 0.708595 0.051 Uiso calc U . R 1 . .
C C4 0.4880(2) 0.3519(5) 0.82656(14) 0.0390(5) Uani d . . . 1 . .
C C5 0.6113(2) 0.2008(5) 0.83767(16) 0.0405(5) Uani d . . . 1 . .
H H6 0.604791 0.101579 0.781696 0.049 Uiso calc U . R 1 . .
H H5 0.618825 0.087608 0.89004 0.049 Uiso calc U . R 1 . .
O O6 0.8729(2) 0.6181(4) 0.97546(15) 0.0739(7) Uani d . . . 1 . .
H H18 0.866371 0.739549 0.940526 0.111 Uiso calc U . R 1 . .
C C6 0.7358(2) 0.3609(5) 0.85437(15) 0.0394(5) Uani d . . . 1 . .
H H7 0.71756 0.4964 0.808422 0.047 Uiso calc U . R 1 . .
C C7 0.8580(2) 0.2279(5) 0.84283(18) 0.0473(6) Uani d . . . 1 . .
H H14 0.931724 0.348595 0.851846 0.057 Uiso calc U . R 1 . .
C C8 0.8432(2) 0.1065(5) 0.7491(2) 0.0485(6) Uani d . . . 1 . .
H H8 0.927947 0.029558 0.747174 0.058 Uiso calc U . R 1 . .
H H13 0.776272 -0.024467 0.741912 0.058 Uiso calc U . R 1 . .
C C9 0.8030(2) 0.2818(5) 0.66932(16) 0.0393(5) Uani d . . . 1 . .
C C10 0.8927(2) 0.4578(5) 0.65401(16) 0.0411(6) Uani d . . . 1 . .
H H11 0.979372 0.467367 0.692418 0.049 Uiso calc U . R 1 . .
C C11 0.8511(2) 0.6154(5) 0.58190(16) 0.0395(5) Uani d . . . 1 . .
C C12 0.8327(2) 0.9115(6) 0.47630(16) 0.0466(6) Uani d . . . 1 . .
H H2 0.820324 1.085611 0.489699 0.056 Uiso calc U . R 1 . .
H H10 0.869137 0.902117 0.421608 0.056 Uiso calc U . R 1 . .
C C13 0.2671(2) 0.6400(6) 0.80777(18) 0.0486(6) Uani d . . . 1 . .
C C14 0.2948(3) 0.4780(6) 0.87916(18) 0.0522(7) Uani d . . . 1 . .
H H20 0.240115 0.463015 0.920729 0.063 Uiso calc U . R 1 . .
C C15 0.4084(3) 0.3351(5) 0.88775(16) 0.0469(6) Uani d . . . 1 . .
H H19 0.431765 0.222829 0.937253 0.056 Uiso calc U . R 1 . .
C C16 0.6768(2) 0.2749(5) 0.61150(16) 0.0431(5) Uani d . . . 1 . .
H H12 0.616777 0.154694 0.621961 0.052 Uiso calc U . R 1 . .
C C17 0.6350(2) 0.4380(5) 0.53863(16) 0.0452(6) Uani d . . . 1 . .
H H9 0.548311 0.432024 0.500076 0.054 Uiso calc U . R 1 . .
C C18 0.7248(2) 0.6066(5) 0.52543(15) 0.0401(5) Uani d . . . 1 . .
C C19 0.7573(3) 0.4759(6) 0.94970(17) 0.0575(8) Uani d . . . 1 . .
H H15 0.680542 0.580004 0.950946 0.069 Uiso calc U . R 1 . .
H H16 0.76157 0.34433 0.995488 0.069 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.376(3) ?
O1 C1 . 1.428(4) ?
O2 C11 . 1.373(3) ?
O2 C12 . 1.435(3) ?
O3 C13 . 1.376(3) ?
O3 C1 . 1.441(4) ?
O4 C18 . 1.379(3) ?
O4 C12 . 1.429(3) ?
O5 C7 . 1.434(3) ?
O5 H17 . 0.84 ?
C1 H3 . 0.99 ?
C1 H1 . 0.99 ?
C2 C3 . 1.368(4) ?
C2 C13 . 1.375(4) ?
C3 C4 . 1.405(4) ?
C3 H4 . 0.95 ?
C4 C15 . 1.388(3) ?
C4 C5 . 1.509(3) ?
C5 C6 . 1.540(3) ?
C5 H6 . 0.99 ?
C5 H5 . 0.99 ?
O6 C19 . 1.412(3) ?
O6 H18 . 0.84 ?
C6 C7 . 1.519(4) ?
C6 C19 . 1.531(4) ?
C6 H7 . 1.0 ?
C7 C8 . 1.532(4) ?
C7 H14 . 1.0 ?
C8 C9 . 1.513(4) ?
C8 H8 . 0.99 ?
C8 H13 . 0.99 ?
C9 C16 . 1.392(3) ?
C9 C10 . 1.404(4) ?
C10 C11 . 1.370(3) ?
C10 H11 . 0.95 ?
C11 C18 . 1.385(3) ?
C12 H2 . 0.99 ?
C12 H10 . 0.99 ?
C13 C14 . 1.368(4) ?
C14 C15 . 1.404(4) ?
C14 H20 . 0.95 ?
C15 H19 . 0.95 ?
C16 C17 . 1.398(4) ?
C16 H12 . 0.95 ?
C17 C18 . 1.367(4) ?
C17 H9 . 0.95 ?
C19 H15 . 0.99 ?
C19 H16 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C1 . . 104.1(2) ?
C11 O2 C12 . . 106.09(18) ?
C13 O3 C1 . . 104.1(2) ?
C18 O4 C12 . . 105.94(18) ?
C7 O5 H17 . . 109.5 ?
O1 C1 O3 . . 107.5(3) ?
O1 C1 H3 . . 110.2 ?
O3 C1 H3 . . 110.2 ?
O1 C1 H1 . . 110.2 ?
O3 C1 H1 . . 110.2 ?
H3 C1 H1 . . 108.5 ?
C3 C2 C13 . . 122.5(3) ?
C3 C2 O1 . . 127.2(2) ?
C13 C2 O1 . . 110.2(2) ?
C2 C3 C4 . . 117.5(2) ?
C2 C3 H4 . . 121.2 ?
C4 C3 H4 . . 121.2 ?
C15 C4 C3 . . 119.3(2) ?
C15 C4 C5 . . 121.9(2) ?
C3 C4 C5 . . 118.8(2) ?
C4 C5 C6 . . 111.9(2) ?
C4 C5 H6 . . 109.2 ?
C6 C5 H6 . . 109.2 ?
C4 C5 H5 . . 109.2 ?
C6 C5 H5 . . 109.2 ?
H6 C5 H5 . . 107.9 ?
C19 O6 H18 . . 109.5 ?
C7 C6 C19 . . 111.8(2) ?
C7 C6 C5 . . 114.3(2) ?
C19 C6 C5 . . 108.0(2) ?
C7 C6 H7 . . 107.5 ?
C19 C6 H7 . . 107.5 ?
C5 C6 H7 . . 107.5 ?
O5 C7 C6 . . 109.1(2) ?
O5 C7 C8 . . 108.5(2) ?
C6 C7 C8 . . 114.59(19) ?
O5 C7 H14 . . 108.2 ?
C6 C7 H14 . . 108.2 ?
C8 C7 H14 . . 108.2 ?
C9 C8 C7 . . 113.5(2) ?
C9 C8 H8 . . 108.9 ?
C7 C8 H8 . . 108.9 ?
C9 C8 H13 . . 108.9 ?
C7 C8 H13 . . 108.9 ?
H8 C8 H13 . . 107.7 ?
C16 C9 C10 . . 119.1(2) ?
C16 C9 C8 . . 120.9(2) ?
C10 C9 C8 . . 120.0(2) ?
C11 C10 C9 . . 117.9(2) ?
C11 C10 H11 . . 121.1 ?
C9 C10 H11 . . 121.1 ?
C10 C11 O2 . . 128.1(2) ?
C10 C11 C18 . . 122.1(2) ?
O2 C11 C18 . . 109.8(2) ?
O4 C12 O2 . . 108.2(2) ?
O4 C12 H2 . . 110.1 ?
O2 C12 H2 . . 110.1 ?
O4 C12 H10 . . 110.1 ?
O2 C12 H10 . . 110.1 ?
H2 C12 H10 . . 108.4 ?
C14 C13 C2 . . 121.7(3) ?
C14 C13 O3 . . 128.5(2) ?
C2 C13 O3 . . 109.7(3) ?
C13 C14 C15 . . 116.4(2) ?
C13 C14 H20 . . 121.8 ?
C15 C14 H20 . . 121.8 ?
C4 C15 C14 . . 122.4(3) ?
C4 C15 H19 . . 118.8 ?
C14 C15 H19 . . 118.8 ?
C9 C16 C17 . . 122.5(2) ?
C9 C16 H12 . . 118.8 ?
C17 C16 H12 . . 118.8 ?
C18 C17 C16 . . 116.9(2) ?
C18 C17 H9 . . 121.6 ?
C16 C17 H9 . . 121.6 ?
C17 C18 O4 . . 128.6(2) ?
C17 C18 C11 . . 121.5(2) ?
O4 C18 C11 . . 109.9(2) ?
O6 C19 C6 . . 113.7(2) ?
O6 C19 H15 . . 108.8 ?
C6 C19 H15 . . 108.8 ?
O6 C19 H16 . . 108.8 ?
C6 C19 H16 . . 108.8 ?
H15 C19 H16 . . 107.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 O1 C1 O3 . . . . -20.3(3) ?
C13 O3 C1 O1 . . . . 20.1(3) ?
C1 O1 C2 C3 . . . . -170.1(3) ?
C1 O1 C2 C13 . . . . 13.0(3) ?
C13 C2 C3 C4 . . . . -1.3(4) ?
O1 C2 C3 C4 . . . . -177.9(2) ?
C2 C3 C4 C15 . . . . 1.9(4) ?
C2 C3 C4 C5 . . . . -177.5(2) ?
C15 C4 C5 C6 . . . . -116.8(3) ?
C3 C4 C5 C6 . . . . 62.6(3) ?
C4 C5 C6 C7 . . . . -165.72(19) ?
C4 C5 C6 C19 . . . . 69.2(3) ?
C19 C6 C7 O5 . . . . 57.7(3) ?
C5 C6 C7 O5 . . . . -65.5(3) ?
C19 C6 C7 C8 . . . . 179.5(2) ?
C5 C6 C7 C8 . . . . 56.4(3) ?
O5 C7 C8 C9 . . . . 178.9(2) ?
C6 C7 C8 C9 . . . . 56.8(3) ?
C7 C8 C9 C16 . . . . -108.3(3) ?
C7 C8 C9 C10 . . . . 70.4(3) ?
C16 C9 C10 C11 . . . . -0.2(3) ?
C8 C9 C10 C11 . . . . -178.9(2) ?
C9 C10 C11 O2 . . . . -179.1(2) ?
C9 C10 C11 C18 . . . . 0.6(4) ?
C12 O2 C11 C10 . . . . -179.1(2) ?
C12 O2 C11 C18 . . . . 1.2(3) ?
C18 O4 C12 O2 . . . . 0.9(3) ?
C11 O2 C12 O4 . . . . -1.3(3) ?
C3 C2 C13 C14 . . . . -0.5(4) ?
O1 C2 C13 C14 . . . . 176.5(2) ?
C3 C2 C13 O3 . . . . -177.5(2) ?
O1 C2 C13 O3 . . . . -0.5(3) ?
C1 O3 C13 C14 . . . . 171.1(3) ?
C1 O3 C13 C2 . . . . -12.1(3) ?
C2 C13 C14 C15 . . . . 1.8(4) ?
O3 C13 C14 C15 . . . . 178.2(2) ?
C3 C4 C15 C14 . . . . -0.6(4) ?
C5 C4 C15 C14 . . . . 178.8(2) ?
C13 C14 C15 C4 . . . . -1.2(4) ?
C10 C9 C16 C17 . . . . -0.4(4) ?
C8 C9 C16 C17 . . . . 178.3(2) ?
C9 C16 C17 C18 . . . . 0.6(4) ?
C16 C17 C18 O4 . . . . 179.8(2) ?
C16 C17 C18 C11 . . . . -0.2(4) ?
C12 O4 C18 C17 . . . . 179.8(3) ?
C12 O4 C18 C11 . . . . -0.1(3) ?
C10 C11 C18 C17 . . . . -0.4(4) ?
O2 C11 C18 C17 . . . . 179.3(2) ?
C10 C11 C18 O4 . . . . 179.6(2) ?
O2 C11 C18 O4 . . . . -0.7(3) ?
C7 C6 C19 O6 . . . . 50.3(3) ?
C5 C6 C19 O6 . . . . 176.9(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H17 O6 2_747 0.84 1.80 2.635(3) 173.8 ?
C1 H3 O2 1_455 0.99 2.47 3.345(3) 146.6 ?
O6 H18 O5 1_565 0.84 1.76 2.549(3) 155.0 ?

