# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2536611'
loop_
_audit_author_name
_audit_author_address
'Xing-de Wu'
; Yunnan Minzu University
China
;
_audit_update_record             
;
2026-03-10 deposited with the CCDC.	2026-05-20 downloaded from the CCDC.
;
_audit_creation_date             2025-12-15
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.05500000000000001
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_moiety         'C15 H20 O4'
_chemical_formula_weight         264.31
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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:
 C4(H4A), C9(H9), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d X=CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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'
_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.
;

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                   7.2678(9)
_cell_length_b                   11.1560(14)
_cell_length_c                   16.214(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1314.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      4.81
_cell_measurement_theta_max      77.11
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6346
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0774 after correction.
The Ratio of minimum to maximum transmission is 0.8415.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            17604
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_theta_min         4.812
_diffrn_reflns_theta_max         77.104
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2765
_reflns_number_gt                2740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.997
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.2432P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2765
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.8941(2) 0.73829(13) 0.39936(9) 0.0321(3) Uani 1 1 d . . . . .
O2 O 0.64251(17) 0.65331(12) 0.34580(8) 0.0238(3) Uani 1 1 d . . . . .
O3 O 0.31715(18) 0.64785(11) 0.25282(8) 0.0247(3) Uani 1 1 d . . . . .
O4 O -0.18419(18) 0.36648(13) 0.30045(10) 0.0320(3) Uani 1 1 d . . . . .
H4 H -0.212762 0.296184 0.287006 0.048 Uiso 1 1 calc R U . . .
C1 C 0.7601(3) 0.67496(16) 0.40854(11) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.6952(3) 0.61264(15) 0.48366(11) 0.0227(4) Uani 1 1 d . . . . .
C3 C 0.7882(3) 0.61839(18) 0.55399(12) 0.0298(4) Uani 1 1 d . . . . .
H3A H 0.899132 0.663252 0.556874 0.036 Uiso 1 1 calc R U . . .
H3B H 0.743900 0.577635 0.601451 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5141(2) 0.55194(16) 0.46419(10) 0.0200(3) Uani 1 1 d . . . . .
H4A H 0.411503 0.602777 0.485779 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4979(2) 0.42634(17) 0.50188(11) 0.0233(4) Uani 1 1 d . . . . .
H5A H 0.543437 0.429988 0.559373 0.028 Uiso 1 1 calc R U . . .
H5B H 0.580628 0.371953 0.471016 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3034(3) 0.37011(17) 0.50291(11) 0.0254(4) Uani 1 1 d . . . . .
H6A H 0.305180 0.298778 0.539223 0.030 Uiso 1 1 calc R U . . .
H6B H 0.216428 0.428638 0.527171 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2324(2) 0.33308(15) 0.41894(11) 0.0221(3) Uani 1 1 d . . . . .
C8 C 0.0845(3) 0.38702(16) 0.38664(11) 0.0227(4) Uani 1 1 d . . . . .
H8 H 0.016573 0.436912 0.423082 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0125(2) 0.37859(17) 0.30025(11) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.069567 0.308516 0.271513 0.029 Uiso 1 1 calc R U . . .
C10 C 0.0572(2) 0.49511(17) 0.25304(11) 0.0242(4) Uani 1 1 d . . . . .
H10A H 0.019605 0.486443 0.194655 0.029 Uiso 1 1 calc R U . . .
H10B H -0.013163 0.562454 0.277233 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2605(2) 0.52249(15) 0.25731(11) 0.0211(4) Uani 1 1 d . . . . .
C12 C 0.3269(2) 0.58577(15) 0.33131(10) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.229199 0.608186 0.371908 0.024 Uiso 1 1 calc R U . . .
C13 C 0.5132(2) 0.55811(14) 0.36857(10) 0.0188(3) Uani 1 1 d . . . . .
H13 H 0.558693 0.480142 0.345966 0.023 Uiso 1 1 calc R U . . .
C14 C 0.3431(3) 0.23649(17) 0.37714(12) 0.0259(4) Uani 1 1 d . . . . .
H14A H 0.274257 0.205461 0.329742 0.039 Uiso 1 1 calc R U . . .
H14B H 0.366507 0.171245 0.416219 0.039 Uiso 1 1 calc R U . . .
H14C H 0.460425 0.269906 0.358239 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3853(3) 0.44242(17) 0.20816(11) 0.0253(4) Uani 1 1 d . . . . .
H15A H 0.350875 0.446100 0.149774 0.038 Uiso 1 1 calc R U . . .
H15B H 0.373602 0.359769 0.227941 0.038 Uiso 1 1 calc R U . . .
H15C H 0.512959 0.469149 0.214675 0.038 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(2) . ?
O2 C1 1.350(2) . ?
O2 C13 1.465(2) . ?
O3 C11 1.460(2) . ?
O3 C12 1.451(2) . ?
O4 H4 0.8400 . ?
O4 C9 1.436(2) . ?
C1 C2 1.480(3) . ?
C2 C3 1.327(3) . ?
C2 C4 1.513(2) . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?
C4 H4A 1.0000 . ?
C4 C5 1.533(2) . ?
C4 C13 1.552(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.547(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(2) . ?
C7 C8 1.339(3) . ?
C7 C14 1.506(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.498(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.543(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.510(2) . ?
C11 C12 1.473(2) . ?
C11 C15 1.502(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.515(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C1 O2 C13 110.21(13) . . ?
C12 O3 C11 60.83(10) . . ?
C9 O4 H4 109.5 . . ?
O1 C1 O2 121.34(17) . . ?
O1 C1 C2 129.11(17) . . ?
O2 C1 C2 109.54(15) . . ?
C1 C2 C4 108.40(14) . . ?
C3 C2 C1 121.48(17) . . ?
C3 C2 C4 130.08(17) . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
C2 C4 H4A 108.8 . . ?
C2 C4 C5 113.11(14) . . ?
C2 C4 C13 101.07(13) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 C13 116.00(14) . . ?
C13 C4 H4A 108.8 . . ?
C4 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C4 C5 C6 116.43(14) . . ?
H5A C5 H5B 107.3 . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C5 114.35(14) . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C8 C7 C6 120.19(16) . . ?
C8 C7 C14 125.06(17) . . ?
C14 C7 C6 114.74(16) . . ?
C7 C8 H8 115.9 . . ?
C7 C8 C9 128.16(16) . . ?
C9 C8 H8 115.9 . . ?
O4 C9 C8 110.56(15) . . ?
O4 C9 H9 109.9 . . ?
O4 C9 C10 106.85(15) . . ?
C8 C9 H9 109.9 . . ?
C8 C9 C10 109.72(14) . . ?
C10 C9 H9 109.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.70(15) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
O3 C11 C10 117.85(15) . . ?
O3 C11 C12 59.28(10) . . ?
O3 C11 C15 111.91(15) . . ?
C12 C11 C10 117.04(15) . . ?
C12 C11 C15 121.30(16) . . ?
C15 C11 C10 116.49(15) . . ?
O3 C12 C11 59.89(10) . . ?
O3 C12 H12 115.0 . . ?
O3 C12 C13 119.40(14) . . ?
C11 C12 H12 115.0 . . ?
C11 C12 C13 121.32(15) . . ?
C13 C12 H12 115.0 . . ?
O2 C13 C4 106.34(13) . . ?
O2 C13 C12 108.97(13) . . ?
O2 C13 H13 109.0 . . ?
C4 C13 H13 109.0 . . ?
C12 C13 C4 114.27(14) . . ?
C12 C13 H13 109.0 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O3 0.84 1.93 2.7620(19) 169.6 3_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -1.7(3) . . . . ?
O1 C1 C2 C4 176.22(18) . . . . ?
O2 C1 C2 C3 179.13(17) . . . . ?
O2 C1 C2 C4 -2.9(2) . . . . ?
O3 C11 C12 C13 -108.14(16) . . . . ?
O3 C12 C13 O2 32.4(2) . . . . ?
O3 C12 C13 C4 151.21(14) . . . . ?
O4 C9 C10 C11 174.00(15) . . . . ?
C1 O2 C13 C4 20.33(18) . . . . ?
C1 O2 C13 C12 143.95(14) . . . . ?
C1 C2 C4 C5 138.94(15) . . . . ?
C1 C2 C4 C13 14.25(17) . . . . ?
C2 C4 C5 C6 166.06(15) . . . . ?
C2 C4 C13 O2 -20.28(16) . . . . ?
C2 C4 C13 C12 -140.53(14) . . . . ?
C3 C2 C4 C5 -43.3(3) . . . . ?
C3 C2 C4 C13 -168.01(19) . . . . ?
C4 C5 C6 C7 70.9(2) . . . . ?
C5 C4 C13 O2 -143.00(14) . . . . ?
C5 C4 C13 C12 96.76(18) . . . . ?
C5 C6 C7 C8 -115.60(19) . . . . ?
C5 C6 C7 C14 63.0(2) . . . . ?
C6 C7 C8 C9 168.74(16) . . . . ?
C7 C8 C9 O4 137.11(19) . . . . ?
C7 C8 C9 C10 -105.3(2) . . . . ?
C8 C9 C10 C11 54.10(19) . . . . ?
C9 C10 C11 O3 -151.39(14) . . . . ?
C9 C10 C11 C12 -83.65(18) . . . . ?
C9 C10 C11 C15 71.3(2) . . . . ?
C10 C11 C12 O3 -107.88(17) . . . . ?
C10 C11 C12 C13 143.98(16) . . . . ?
C11 O3 C12 C13 111.29(17) . . . . ?
C11 C12 C13 O2 103.09(17) . . . . ?
C11 C12 C13 C4 -138.13(16) . . . . ?
C12 O3 C11 C10 106.50(18) . . . . ?
C12 O3 C11 C15 -114.35(17) . . . . ?
C13 O2 C1 O1 169.73(17) . . . . ?
C13 O2 C1 C2 -11.06(19) . . . . ?
C13 C4 C5 C6 -77.81(19) . . . . ?
C14 C7 C8 C9 -9.7(3) . . . . ?
C15 C11 C12 O3 98.44(17) . . . . ?
C15 C11 C12 C13 -9.7(2) . . . . ?

