# 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_26942_d_0m
_database_code_depnum_ccdc_archive 'CCDC 2450214'
loop_
_audit_author_name
_audit_author_address
'Zhao Huan'
;Jinan university
China
;
_audit_update_record             
;
2025-06-04 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;
_audit_creation_date             2025-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 O6, H2 O'
_chemical_formula_sum            'C21 H22 O7'
_chemical_formula_weight         386.38
_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                   9.6221(2)
_cell_length_b                   8.1595(2)
_cell_length_c                   11.5469(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.6252(9)
_cell_angle_gamma                90
_cell_volume                     906.20(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      68.222
_cell_measurement_theta_min      5.904
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1023 before and 0.0622 after correction. The Ratio of minimum to maximum transmission is 0.8596. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34765
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         3.830
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'B ruler D8 venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3252
_reflns_number_total             3292
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.102
_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)+(0.0581P)²+0.2832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0944
_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,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C14(H14)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C20(H20), C11(H11), C12(H12)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.31115(18) 0.1429(2) 0.73652(15) 0.0193(4) Uani 1 1 d . . . . .
O1 O 0.36352(18) -0.3434(2) 0.55866(15) 0.0200(4) Uani 1 1 d . . . . .
O4 O 0.1972(2) 0.0972(2) 0.96705(17) 0.0282(5) Uani 1 1 d . . . . .
O3 O 0.4127(2) -0.1517(3) 0.43001(16) 0.0281(5) Uani 1 1 d . . . . .
O6 O 0.08882(19) -0.4448(3) 0.54831(17) 0.0274(5) Uani 1 1 d . . . . .
O5 O 0.0649(2) -0.5302(3) 1.25499(19) 0.0322(5) Uani 1 1 d . . . . .
C6 C 0.3121(2) 0.0010(3) 0.8023(2) 0.0168(5) Uani 1 1 d . . . . .
C4 C 0.3707(3) -0.0675(3) 0.6240(2) 0.0180(5) Uani 1 1 d . . . . .
C9 C 0.2732(2) -0.3216(3) 0.8822(2) 0.0148(5) Uani 1 1 d . . . . .
C10 C 0.3549(2) -0.3009(3) 0.7721(2) 0.0158(5) Uani 1 1 d . . . . .
O7 O 0.3124(3) -0.6408(3) 0.4107(2) 0.0404(5) Uani 1 1 d . . . . .
H7A H 0.3097 -0.5460 0.4450 0.061 Uiso 1 1 d G . . . .
H7B H 0.2400 -0.6409 0.3638 0.061 Uiso 1 1 d G . . . .
C8 C 0.2298(2) -0.1920(3) 0.9477(2) 0.0147(5) Uani 1 1 d . . . . .
C20 C 0.3474(3) 0.0968(3) 0.6273(2) 0.0195(5) Uani 1 1 d . . . . .
H20 H 0.3551 0.1691 0.5633 0.023 Uiso 1 1 calc R . . . .
C5 C 0.3515(2) -0.1259(3) 0.7375(2) 0.0155(5) Uani 1 1 d . . . . .
C1 C 0.2916(2) -0.3908(3) 0.6642(2) 0.0176(5) Uani 1 1 d . . . . .
H1 H 0.3051 -0.5113 0.6760 0.021 Uiso 1 1 calc R . . . .
C17 C 0.1021(3) -0.4043(3) 1.2116(2) 0.0212(5) Uani 1 1 d . . . . .
C19 C 0.5057(3) -0.3612(3) 0.7955(2) 0.0220(5) Uani 1 1 d . . . . .
H19A H 0.5047 -0.4783 0.8143 0.033 Uiso 1 1 calc GR . . . .
H19B H 0.5474 -0.2999 0.8606 0.033 Uiso 1 1 calc GR . . . .
H19C H 0.5604 -0.3436 0.7262 0.033 Uiso 1 1 calc GR . . . .
C18 C 0.3497(3) -0.3629(4) 1.1718(2) 0.0233(6) Uani 1 1 d . . . . .
H18A H 0.3817 -0.4661 1.2068 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.3441 -0.2787 1.2319 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.4154 -0.3279 1.1134 0.035 Uiso 1 1 calc GR . . . .
C7 C 0.2448(2) -0.0175(3) 0.9130(2) 0.0172(5) Uani 1 1 d . . . . .
C11 C 0.2480(3) -0.4906(3) 0.9206(2) 0.0183(5) Uani 1 1 d . . . . .
H11 H 0.2574 -0.5775 0.8667 0.022 Uiso 1 1 calc R . . . .
C2 C 0.1368(3) -0.3590(3) 0.6473(2) 0.0196(5) Uani 1 1 d . . . . .
H2A H 0.0867 -0.3966 0.7161 0.024 Uiso 1 1 calc R . . . .
H2B H 0.1196 -0.2402 0.6372 0.024 Uiso 1 1 calc R . . . .
C16 C 0.0558(3) -0.2322(4) 1.2428(3) 0.0257(6) Uani 1 1 d . . . . .
H16A H 0.0889 -0.2036 1.3222 0.031 Uiso 1 1 calc R . . . .
H16B H -0.0469 -0.2244 1.2392 0.031 Uiso 1 1 calc R . . . .
C13 C 0.2041(2) -0.3883(3) 1.1136(2) 0.0172(5) Uani 1 1 d . . . . .
C3 C 0.3854(3) -0.1827(3) 0.5277(2) 0.0208(6) Uani 1 1 d . . . . .
C14 C 0.1465(2) -0.2345(3) 1.0527(2) 0.0156(5) Uani 1 1 d . . . . .
H14 H 0.0523 -0.2663 1.0214 0.019 Uiso 1 1 calc R . . . .
C12 C 0.2122(3) -0.5263(3) 1.0292(2) 0.0193(5) Uani 1 1 d . . . . .
H12 H 0.1927 -0.6357 1.0516 0.023 Uiso 1 1 calc R . . . .
C15 C 0.1197(3) -0.1161(3) 1.1539(2) 0.0202(5) Uani 1 1 d . . . . .
H15A H 0.2072 -0.0666 1.1844 0.024 Uiso 1 1 calc R . . . .
H15B H 0.0540 -0.0280 1.1304 0.024 Uiso 1 1 calc R . . . .
C21 C -0.0515(3) -0.4081(4) 0.5191(2) 0.0278(6) Uani 1 1 d . . . . .
H21A H -0.1106 -0.4408 0.5828 0.042 Uiso 1 1 calc GR . . . .
H21B H -0.0798 -0.4679 0.4487 0.042 Uiso 1 1 calc GR . . . .
H21C H -0.0613 -0.2900 0.5055 0.042 Uiso 1 1 calc GR . . . .


_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
O2 C6 1.385(3) . ?
O2 C20 1.371(3) . ?
O1 C1 1.470(3) . ?
O1 C3 1.377(3) . ?
O4 C7 1.221(3) . ?
O3 C3 1.193(3) . ?
O6 C2 1.407(3) . ?
O6 C21 1.415(3) . ?
O5 C17 1.202(3) . ?
C6 C5 1.339(4) . ?
C6 C7 1.457(3) . ?
C4 C20 1.360(4) . ?
C4 C5 1.411(4) . ?
C4 C3 1.466(4) . ?
C9 C10 1.524(3) . ?
C9 C8 1.372(3) . ?
C9 C11 1.471(4) . ?
C10 C5 1.483(3) . ?
C10 C1 1.555(3) . ?
C10 C19 1.548(3) . ?
C8 C7 1.487(3) . ?
C8 C14 1.513(4) . ?
C1 C2 1.520(3) . ?
C17 C16 1.520(4) . ?
C17 C13 1.525(3) . ?
C18 C13 1.550(3) . ?
C11 C12 1.341(4) . ?
C16 C15 1.538(4) . ?
C13 C14 1.535(3) . ?
C13 C12 1.493(3) . ?
C14 C15 1.544(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
C20 O2 C6 106.1(2) . . ?
C3 O1 C1 122.98(19) . . ?
C2 O6 C21 112.1(2) . . ?
O2 C6 C7 124.8(2) . . ?
C5 C6 O2 109.8(2) . . ?
C5 C6 C7 123.4(2) . . ?
C20 C4 C5 106.4(2) . . ?
C20 C4 C3 132.3(3) . . ?
C5 C4 C3 120.4(2) . . ?
C8 C9 C10 123.2(2) . . ?
C8 C9 C11 120.1(2) . . ?
C11 C9 C10 116.7(2) . . ?
C9 C10 C1 114.65(19) . . ?
C9 C10 C19 108.81(19) . . ?
C5 C10 C9 108.9(2) . . ?
C5 C10 C1 103.50(19) . . ?
C5 C10 C19 111.5(2) . . ?
C19 C10 C1 109.48(19) . . ?
C9 C8 C7 123.8(2) . . ?
C9 C8 C14 116.2(2) . . ?
C7 C8 C14 119.6(2) . . ?
C4 C20 O2 110.0(2) . . ?
C6 C5 C4 107.7(2) . . ?
C6 C5 C10 126.8(2) . . ?
C4 C5 C10 125.0(2) . . ?
O1 C1 C10 110.93(19) . . ?
O1 C1 C2 109.35(19) . . ?
C2 C1 C10 112.50(19) . . ?
O5 C17 C16 126.7(2) . . ?
O5 C17 C13 126.0(2) . . ?
C16 C17 C13 107.2(2) . . ?
O4 C7 C6 123.5(2) . . ?
O4 C7 C8 123.7(2) . . ?
C6 C7 C8 112.6(2) . . ?
C12 C11 C9 122.3(2) . . ?
O6 C2 C1 108.5(2) . . ?
C17 C16 C15 106.6(2) . . ?
C17 C13 C18 106.44(19) . . ?
C17 C13 C14 100.3(2) . . ?
C14 C13 C18 113.6(2) . . ?
C12 C13 C17 117.8(2) . . ?
C12 C13 C18 108.7(2) . . ?
C12 C13 C14 110.0(2) . . ?
O1 C3 C4 113.3(2) . . ?
O3 C3 O1 119.1(2) . . ?
O3 C3 C4 127.6(2) . . ?
C8 C14 C13 111.23(19) . . ?
C8 C14 C15 124.5(2) . . ?
C13 C14 C15 103.3(2) . . ?
C11 C12 C13 117.8(2) . . ?
C16 C15 C14 101.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
