# 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_20649
_audit_block_doi                 10.5517/ccdc.csd.cc2g57nk
_database_code_depnum_ccdc_archive 'CCDC 2269158'
loop_
_audit_author_name
_audit_author_address
'tong tian'
;xiangtan university
China
;
_audit_update_record             
;
2024-05-28 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-15
_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         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7949(8)
_cell_length_b                   6.9944(3)
_cell_length_c                   14.1314(8)
_cell_angle_alpha                90
_cell_angle_beta                 117.585(7)
_cell_angle_gamma                90
_cell_volume                     1208.50(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1811
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.8830
_cell_measurement_theta_min      6.2870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39369
_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    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4219
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.936
_diffrn_reflns_theta_min         3.615
_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 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  -4.00   1.00    1.00    --  -40.98 125.00  30.00   49
  2  ω   -115.00 -18.00   1.00    1.00    --  -40.98 -37.00 -60.00   97
  3  ω   -113.00 -19.00   1.00    1.00    --  -40.98 -57.00-150.00   94
  4  ω     38.00 137.00   1.00    1.62    --  107.58 -61.00   0.00   99
  5  ω     98.00 125.00   1.00    1.62    --  107.58  38.00 146.00   27
  6  ω    135.00 168.00   1.00    1.62    --  107.58 125.00  30.00   33
  7  ω     87.00 164.00   1.00    1.62    --  107.58  30.00-180.00   77
  8  ω     34.00 106.00   1.00    1.62    --  107.58-125.00   0.00   72
  9  ω     49.00 136.00   1.00    1.62    --  107.58 -30.00 150.00   87
;
_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      -0.1221506000
_diffrn_orient_matrix_UB_12      -0.0362387000
_diffrn_orient_matrix_UB_13      -0.0748333000
_diffrn_orient_matrix_UB_21      -0.0115441000
_diffrn_orient_matrix_UB_22      -0.0968961000
_diffrn_orient_matrix_UB_23      0.0922323000
_diffrn_orient_matrix_UB_31      -0.0285686000
_diffrn_orient_matrix_UB_32      0.1943953000
_diffrn_orient_matrix_UB_33      0.0319479000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1928
_reflns_number_total             2369
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0801
_refine_ls_restrained_S_all      1.089
_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)+(0.1413P)²+0.0928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5A), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69902(15) 0.8730(3) 0.4165(2) 0.0501(6) Uani 1 1 d . . . . .
O2 O 0.79947(12) 0.6225(2) 0.64055(13) 0.0318(5) Uani 1 1 d . . . . .
O3 O 0.94044(13) 0.6232(3) 0.60354(13) 0.0346(5) Uani 1 1 d . . . . .
H3 H 0.974496 0.660385 0.667170 0.052 Uiso 1 1 calc R U . . .
O4 O 0.94130(13) 0.2101(3) 0.69325(13) 0.0359(5) Uani 1 1 d . . . . .
O5 O 1.07775(13) 0.1754(3) 0.65116(14) 0.0400(5) Uani 1 1 d . . . . .
H5 H 1.114458 0.156873 0.717154 0.060 Uiso 1 1 calc R U . . .
C1 C 0.51294(18) 0.8308(3) 0.37148(17) 0.0290(5) Uani 1 1 d . . . . .
C2 C 0.4945(2) 1.0257(4) 0.37384(19) 0.0337(6) Uani 1 1 d . . . . .
H2 H 0.553555 1.112739 0.393516 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3911(2) 1.0944(4) 0.3479(2) 0.0375(6) Uani 1 1 d . . . . .
H3A H 0.379512 1.227875 0.349770 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3045(2) 0.9680(4) 0.31908(19) 0.0360(6) Uani 1 1 d . . . . .
H4 H 0.233694 1.014663 0.302207 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3214(2) 0.7745(4) 0.3150(2) 0.0370(6) Uani 1 1 d . . . . .
H5A H 0.261738 0.688297 0.293784 0.044 Uiso 1 1 calc R U . . .
C6 C 0.42524(18) 0.7052(3) 0.34176(18) 0.0327(6) Uani 1 1 d . . . . .
H6 H 0.436521 0.571624 0.339790 0.039 Uiso 1 1 calc R U . . .
C7 C 0.62725(18) 0.7615(4) 0.40527(18) 0.0322(6) Uani 1 1 d . . . . .
C8 C 0.65116(17) 0.5516(3) 0.42561(17) 0.0293(5) Uani 1 1 d . . . . .
H8A H 0.609473 0.481113 0.357877 0.035 Uiso 1 1 calc R U . . .
H8B H 0.625343 0.507318 0.476617 0.035 Uiso 1 1 calc R U . . .
C9 C 0.77195(17) 0.5032(3) 0.47013(16) 0.0275(5) Uani 1 1 d . . . . .
H9 H 0.799001 0.555406 0.420768 0.033 Uiso 1 1 calc R U . . .
C10 C 0.83753(18) 0.5916(3) 0.57915(18) 0.0287(5) Uani 1 1 d . . . . .
C11 C 0.78618(17) 0.2844(3) 0.47609(17) 0.0293(5) Uani 1 1 d . . . . .
H11A H 0.762255 0.234679 0.527513 0.035 Uiso 1 1 calc R U . . .
H11B H 0.736412 0.230511 0.405207 0.035 Uiso 1 1 calc R U . . .
C12 C 0.90087(18) 0.2100(3) 0.50857(18) 0.0308(6) Uani 1 1 d . . . . .
H12A H 0.895036 0.080216 0.478456 0.037 Uiso 1 1 calc R U . . .
H12B H 0.935630 0.293244 0.476252 0.037 Uiso 1 1 calc R U . . .
C13 C 0.97421(18) 0.2009(3) 0.62689(19) 0.0299(5) Uani 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 C7 1.212(3) . ?
O2 C10 1.224(3) . ?
O3 H3 0.8400 . ?
O3 C10 1.315(3) . ?
O4 C13 1.218(3) . ?
O5 H5 0.8400 . ?
O5 C13 1.317(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.393(3) . ?
C1 C7 1.501(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.387(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5A 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.503(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.522(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.511(3) . ?
C9 C11 1.540(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.521(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.502(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
C10 O3 H3 109.5 . . ?
C13 O5 H5 109.5 . . ?
C2 C1 C6 118.8(2) . . ?
C2 C1 C7 119.1(2) . . ?
C6 C1 C7 122.0(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3A 120.1 . . ?
C2 C3 C4 119.9(2) . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5A 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
O1 C7 C1 120.5(2) . . ?
O1 C7 C8 120.7(2) . . ?
C1 C7 C8 118.8(2) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.42(19) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9 108.7 . . ?
C8 C9 C11 109.32(18) . . ?
C10 C9 C8 110.77(19) . . ?
C10 C9 H9 108.7 . . ?
C10 C9 C11 110.47(17) . . ?
C11 C9 H9 108.7 . . ?
O2 C10 O3 123.4(2) . . ?
O2 C10 C9 123.0(2) . . ?
O3 C10 C9 113.6(2) . . ?
C9 C11 H11A 108.2 . . ?
C9 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 C9 116.42(19) . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C11 114.89(19) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
O4 C13 O5 123.5(2) . . ?
O4 C13 C12 123.7(2) . . ?
O5 C13 C12 112.7(2) . . ?

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 C7 C8 C9 5.5(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C7 C8 C9 -174.10(18) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C7 O1 -12.8(3) . . . . ?
C2 C1 C7 C8 166.8(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C6 C1 C7 O1 169.8(2) . . . . ?
C6 C1 C7 C8 -10.6(3) . . . . ?
C7 C1 C2 C3 -177.1(2) . . . . ?
C7 C1 C6 C5 177.5(2) . . . . ?
C7 C8 C9 C10 64.4(2) . . . . ?
C7 C8 C9 C11 -173.65(18) . . . . ?
C8 C9 C10 O2 29.0(3) . . . . ?
C8 C9 C10 O3 -154.19(19) . . . . ?
C8 C9 C11 C12 174.13(18) . . . . ?
C9 C11 C12 C13 84.3(2) . . . . ?
C10 C9 C11 C12 -63.7(2) . . . . ?
C11 C9 C10 O2 -92.3(3) . . . . ?
C11 C9 C10 O3 84.5(2) . . . . ?
C11 C12 C13 O4 15.7(3) . . . . ?
C11 C12 C13 O5 -166.4(2) . . . . ?

_olex2_date_sample_data_collection 2023-04-13
_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 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.512
