# Supplementary Information (SI) for Green Chemistry.
# 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_DEBQ_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2453221'
loop_
_audit_author_name
_audit_author_address
'Guang Wu'
;The University of California, Santa Barbara
United States of America
;
_audit_update_record             
;
2025-05-22 deposited with the CCDC.	2026-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 O4'
_chemical_formula_weight         196.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3761(17)
_cell_length_b                   7.8776(15)
_cell_length_c                   13.285(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.051(11)
_cell_angle_gamma                90
_cell_volume                     978.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1179
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.10

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6736
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Apex 2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5810
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         27.202
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2155
_reflns_number_gt                1522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0374P)²+0.3802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2155
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.42296(16) 0.3190(2) 0.40372(12) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.45590(16) 0.2758(2) 0.51265(12) 0.0178(4) Uani 1 1 d . . . . .
C3 C 0.36546(16) 0.3149(2) 0.58257(12) 0.0210(4) Uani 1 1 d . . . . .
H3 H 0.3901 0.2885 0.6514 0.025 Uiso 1 1 calc R U . . .
C4 C 0.22867(17) 0.3981(2) 0.55413(13) 0.0238(4) Uani 1 1 d . . . . .
C5 C 0.19278(16) 0.4422(2) 0.44828(12) 0.0219(4) Uani 1 1 d . . . . .
H5 H 0.1039 0.4953 0.4295 0.026 Uiso 1 1 calc R U . . .
C6 C 0.28365(16) 0.4085(2) 0.37778(12) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.62100(16) 0.1407(2) 0.62868(12) 0.0202(4) Uani 1 1 d . . . . .
H7A H 0.5490 0.0605 0.6520 0.024 Uiso 1 1 calc R U . . .
H7B H 0.6267 0.2398 0.6746 0.024 Uiso 1 1 calc R U . . .
C8 C 0.76439(17) 0.0554(2) 0.62788(13) 0.0239(4) Uani 1 1 d . . . . .
H8A H 0.7577 -0.0408 0.5811 0.036 Uiso 1 1 calc R U . . .
H8B H 0.7938 0.0148 0.6959 0.036 Uiso 1 1 calc R U . . .
H8C H 0.8351 0.1368 0.6061 0.036 Uiso 1 1 calc R U . . .
C9 C 0.13371(16) 0.5229(2) 0.24368(13) 0.0217(4) Uani 1 1 d . . . . .
H9A H 0.1185 0.6274 0.2829 0.026 Uiso 1 1 calc R U . . .
H9B H 0.0527 0.4448 0.2521 0.026 Uiso 1 1 calc R U . . .
C10 C 0.14293(18) 0.5654(3) 0.13428(13) 0.0294(4) Uani 1 1 d . . . . .
H10A H 0.2278 0.6353 0.1263 0.044 Uiso 1 1 calc R U . . .
H10B H 0.0572 0.6282 0.1097 0.044 Uiso 1 1 calc R U . . .
H10C H 0.1497 0.4604 0.0954 0.044 Uiso 1 1 calc R U . . .
O1 O 0.50223(12) 0.27989(16) 0.33959(9) 0.0254(3) Uani 1 1 d . . . . .
O2 O 0.14331(13) 0.42695(19) 0.61817(9) 0.0366(4) Uani 1 1 d . . . . .
O3 O 0.58157(11) 0.19473(15) 0.52629(8) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.26708(11) 0.44299(15) 0.27867(8) 0.0208(3) 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
C1 O1 1.2096(19) . ?
C1 C2 1.497(2) . ?
C1 C6 1.503(2) . ?
C2 C3 1.337(2) . ?
C2 O3 1.3413(18) . ?
C3 C4 1.466(2) . ?
C3 H3 0.9500 . ?
C4 O2 1.230(2) . ?
C4 C5 1.464(2) . ?
C5 C6 1.337(2) . ?
C5 H5 0.9500 . ?
C6 O4 1.3427(19) . ?
C7 O3 1.4481(18) . ?
C7 C8 1.504(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O4 1.4470(18) . ?
C9 C10 1.500(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
O1 C1 C2 121.85(14) . . ?
O1 C1 C6 121.70(15) . . ?
C2 C1 C6 116.42(14) . . ?
C3 C2 O3 127.59(15) . . ?
C3 C2 C1 121.42(14) . . ?
O3 C2 C1 110.99(13) . . ?
C2 C3 C4 120.68(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
O2 C4 C5 120.26(15) . . ?
O2 C4 C3 120.31(16) . . ?
C5 C4 C3 119.41(15) . . ?
C6 C5 C4 120.75(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 O4 127.71(14) . . ?
C5 C6 C1 121.28(15) . . ?
O4 C6 C1 111.00(13) . . ?
O3 C7 C8 107.08(13) . . ?
O3 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O3 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C10 107.50(13) . . ?
O4 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O4 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 O3 C7 115.50(12) . . ?
C6 O4 C9 116.14(12) . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.047

