# Supplementary Information (SI) for Green 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_cu_2225_0m
_database_code_depnum_ccdc_archive 'CCDC 2409595'
loop_
_audit_author_name
_audit_author_address
'Li Liu'
;Inner Mongolia Univeresity
China
;
_audit_update_record             
;
2024-12-12 deposited with the CCDC.	2025-04-08 downloaded from the CCDC.
;
_audit_creation_date             2024-07-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H10 O5'
_chemical_formula_sum            'C6 H10 O5'
_chemical_formula_weight         162.14
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   6.66170(10)
_cell_length_b                   7.5013(2)
_cell_length_c                   13.2780(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     663.52(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7619
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.232
_cell_measurement_theta_min      6.668
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    1.245
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1562 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.8306.
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    1.623
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.13
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.268
_diffrn_reflns_theta_min         6.668
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1176
_reflns_number_total             1200
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0230
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²+0.1404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0583
_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:
 C1(H1A), C2(H2A), C3(H3), C5(H5A), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), 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 0.7757(2) 0.77126(16) 0.60132(9) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.796578 0.850985 0.559257 0.036 Uiso 1 1 calc R U . . .
C1 C 0.6763(2) 0.6250(2) 0.55373(12) 0.0169(4) Uani 1 1 d . . . . .
H1A H 0.628179 0.664108 0.486729 0.020 Uiso 1 1 calc R U . . .
O2 O 0.33346(17) 0.50268(16) 0.55987(9) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.346643 0.392879 0.555879 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4931(2) 0.5750(2) 0.61882(12) 0.0174(4) Uani 1 1 d . . . . .
H2A H 0.443254 0.685277 0.651281 0.021 Uiso 1 1 calc R U . . .
O3 O 0.70214(18) 0.51789(19) 0.76531(9) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.5493(3) 0.4440(3) 0.70181(13) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.429431 0.412298 0.742091 0.026 Uiso 1 1 calc R U . . .
O4 O 0.63501(18) 0.29017(16) 0.65907(9) 0.0220(3) Uani 1 1 d . . . . .
C4 C 0.8927(3) 0.4557(3) 0.72670(13) 0.0253(4) Uani 1 1 d . . . . .
H4A H 0.960692 0.378991 0.775718 0.030 Uiso 1 1 calc R U . . .
H4B H 0.980750 0.555943 0.709713 0.030 Uiso 1 1 calc R U . . .
O5 O 0.7548(2) 0.35466(16) 0.45938(9) 0.0217(3) Uani 1 1 d . . . . .
H5 H 0.793674 0.395385 0.404630 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8340(2) 0.3512(2) 0.63279(13) 0.0201(4) Uani 1 1 d . . . . .
H5A H 0.925870 0.249241 0.622032 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8225(2) 0.4675(2) 0.53931(12) 0.0178(4) Uani 1 1 d . . . . .
H6 H 0.957887 0.513855 0.523088 0.021 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0289(7) 0.0197(6) 0.0243(6) 0.0003(5) -0.0027(5) -0.0084(5)
C1 0.0176(8) 0.0170(8) 0.0160(7) 0.0016(6) -0.0022(7) -0.0025(7)
O2 0.0164(6) 0.0184(6) 0.0301(6) 0.0017(5) -0.0049(5) -0.0009(5)
C2 0.0149(8) 0.0189(8) 0.0184(8) -0.0019(7) -0.0002(7) 0.0012(6)
O3 0.0267(7) 0.0377(7) 0.0159(6) -0.0047(5) -0.0022(5) 0.0062(6)
C3 0.0203(8) 0.0274(10) 0.0172(8) 0.0024(7) 0.0031(7) 0.0011(7)
O4 0.0230(6) 0.0206(6) 0.0223(6) 0.0046(5) 0.0014(5) -0.0005(5)
C4 0.0239(10) 0.0323(10) 0.0199(8) 0.0002(8) -0.0049(7) 0.0054(8)
O5 0.0267(6) 0.0229(6) 0.0156(6) -0.0015(5) 0.0025(5) 0.0014(5)
C5 0.0172(8) 0.0237(8) 0.0194(8) 0.0006(7) -0.0016(7) 0.0048(7)
C6 0.0140(8) 0.0234(8) 0.0159(7) -0.0007(7) 0.0002(6) -0.0008(7)

_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 H1 0.8300 . ?
O1 C1 1.4290(19) . ?
C1 H1A 0.9900 . ?
C1 C2 1.542(2) . ?
C1 C6 1.543(2) . ?
O2 H2 0.8300 . ?
O2 C2 1.428(2) . ?
C2 H2A 0.9900 . ?
C2 C3 1.523(2) . ?
O3 C3 1.434(2) . ?
O3 C4 1.446(2) . ?
C3 H3 0.9900 . ?
C3 O4 1.407(2) . ?
O4 C5 1.445(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 C5 1.524(2) . ?
O5 H5 0.8300 . ?
O5 C6 1.431(2) . ?
C5 H5A 0.9900 . ?
C5 C6 1.519(2) . ?
C6 H6 0.9900 . ?

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 O1 H1 109.5 . . ?
O1 C1 H1A 108.6 . . ?
O1 C1 C2 107.80(13) . . ?
O1 C1 C6 110.47(13) . . ?
C2 C1 H1A 108.6 . . ?
C2 C1 C6 112.54(13) . . ?
C6 C1 H1A 108.6 . . ?
C2 O2 H2 109.5 . . ?
C1 C2 H2A 107.8 . . ?
O2 C2 C1 112.00(13) . . ?
O2 C2 H2A 107.8 . . ?
O2 C2 C3 109.54(14) . . ?
C3 C2 C1 111.59(14) . . ?
C3 C2 H2A 107.8 . . ?
C3 O3 C4 106.88(13) . . ?
C2 C3 H3 110.4 . . ?
O3 C3 C2 110.54(15) . . ?
O3 C3 H3 110.4 . . ?
O4 C3 C2 109.70(14) . . ?
O4 C3 O3 105.42(14) . . ?
O4 C3 H3 110.4 . . ?
C3 O4 C5 102.11(13) . . ?
O3 C4 H4A 111.1 . . ?
O3 C4 H4B 111.1 . . ?
O3 C4 C5 103.35(14) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C6 O5 H5 109.5 . . ?
O4 C5 C4 101.57(14) . . ?
O4 C5 H5A 110.9 . . ?
O4 C5 C6 109.46(13) . . ?
C4 C5 H5A 110.9 . . ?
C6 C5 C4 112.70(14) . . ?
C6 C5 H5A 110.9 . . ?
C1 C6 H6 109.5 . . ?
O5 C6 C1 110.23(13) . . ?
O5 C6 C5 106.38(13) . . ?
O5 C6 H6 109.5 . . ?
C5 C6 C1 111.72(13) . . ?
C5 C6 H6 109.5 . . ?

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 O2 150.08(13) . . . . ?
O1 C1 C2 C3 -86.70(16) . . . . ?
O1 C1 C6 O5 -156.76(13) . . . . ?
O1 C1 C6 C5 85.19(16) . . . . ?
C1 C2 C3 O3 58.45(18) . . . . ?
C1 C2 C3 O4 -57.37(18) . . . . ?
O2 C2 C3 O3 -176.93(13) . . . . ?
O2 C2 C3 O4 67.24(17) . . . . ?
C2 C1 C6 O5 82.69(16) . . . . ?
C2 C1 C6 C5 -35.36(19) . . . . ?
C2 C3 O4 C5 75.89(16) . . . . ?
O3 C3 O4 C5 -43.14(15) . . . . ?
O3 C4 C5 O4 -28.86(16) . . . . ?
O3 C4 C5 C6 88.16(17) . . . . ?
C3 O3 C4 C5 3.47(17) . . . . ?
C3 O4 C5 C4 43.92(15) . . . . ?
C3 O4 C5 C6 -75.43(15) . . . . ?
O4 C5 C6 C1 55.99(18) . . . . ?
O4 C5 C6 O5 -64.34(16) . . . . ?
C4 O3 C3 C2 -94.18(16) . . . . ?
C4 O3 C3 O4 24.29(17) . . . . ?
C4 C5 C6 C1 -56.25(19) . . . . ?
C4 C5 C6 O5 -176.58(13) . . . . ?
C6 C1 C2 O2 -87.85(16) . . . . ?
C6 C1 C2 C3 35.37(18) . . . . ?

_shelx_res_file                  
;
TITL cu_2225_0m_a.res in P2(1)2(1)2(1)
    cu_2225_0m.res
    created by SHELXL-2018/3 at 11:49:03 on 10-Jul-2024
REM Old TITL cu_2225_0m in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.086, Rweak 0.024, Alpha 0.004
REM <I/s> 0.332 for 17 systematic absences, Orientation as input
REM Flack x = 0.070 ( 0.060 ) from 468 Parsons' quotients
REM Formula found by SHELXT: C6 O5
CELL 1.54178 6.6617 7.5013 13.278 90 90 90
ZERR 4 0.0001 0.0002 0.0003 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H O
UNIT 24 40 20

L.S. 4 0 0
PLAN  5
SIZE 0.11 0.12 0.13
TEMP -50.15
CONF
BOND
list 4
fmap 2 53
MORE -1
BOND $H
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\cu_2225_0m.hkl">
REM </olex2.extras>

WGHT    0.029800    0.140400
FVAR       1.37858
O1    3    0.775716    0.771256    0.601318    11.00000    0.02890    0.01973 =
         0.02434    0.00034   -0.00271   -0.00842
AFIX 147
H1    2    0.796578    0.850985    0.559257    11.00000   -1.50000
AFIX   0
C1    1    0.676266    0.624986    0.553726    11.00000    0.01763    0.01702 =
         0.01597    0.00163   -0.00221   -0.00253
AFIX  13
H1A   2    0.628179    0.664108    0.486729    11.00000   -1.20000
AFIX   0
O2    3    0.333455    0.502678    0.559871    11.00000    0.01645    0.01839 =
         0.03011    0.00167   -0.00489   -0.00093
AFIX 147
H2    2    0.346643    0.392879    0.555879    11.00000   -1.50000
AFIX   0
C2    1    0.493096    0.575016    0.618822    11.00000    0.01490    0.01885 =
         0.01842   -0.00195   -0.00023    0.00125
AFIX  13
H2A   2    0.443254    0.685277    0.651281    11.00000   -1.20000
AFIX   0
O3    3    0.702135    0.517890    0.765315    11.00000    0.02665    0.03767 =
         0.01591   -0.00473   -0.00219    0.00623
C3    1    0.549266    0.444037    0.701806    11.00000    0.02033    0.02737 =
         0.01716    0.00242    0.00306    0.00109
AFIX  13
H3    2    0.429431    0.412298    0.742091    11.00000   -1.20000
AFIX   0
O4    3    0.635012    0.290167    0.659066    11.00000    0.02303    0.02062 =
         0.02226    0.00457    0.00138   -0.00049
C4    1    0.892654    0.455729    0.726700    11.00000    0.02386    0.03227 =
         0.01985    0.00022   -0.00486    0.00542
AFIX  23
H4A   2    0.960692    0.378991    0.775718    11.00000   -1.20000
H4B   2    0.980750    0.555943    0.709713    11.00000   -1.20000
AFIX   0
O5    3    0.754779    0.354655    0.459376    11.00000    0.02666    0.02285 =
         0.01560   -0.00147    0.00250    0.00144
AFIX 147
H5    2    0.793674    0.395385    0.404630    11.00000   -1.50000
AFIX   0
C5    1    0.833998    0.351214    0.632788    11.00000    0.01718    0.02375 =
         0.01944    0.00055   -0.00164    0.00483
AFIX  13
H5A   2    0.925870    0.249241    0.622032    11.00000   -1.20000
AFIX   0
C6    1    0.822535    0.467544    0.539312    11.00000    0.01404    0.02340 =
         0.01593   -0.00066    0.00023   -0.00084
AFIX  13
H6    2    0.957887    0.513855    0.523088    11.00000   -1.20000
AFIX   0
HKLF 4




REM  cu_2225_0m_a.res in P2(1)2(1)2(1)
REM wR2 = 0.058329, GooF = S = 1.08654, Restrained GooF = 1.08654 for all data
REM R1 = 0.022958 for 1176 Fo > 4sig(Fo) and 0.023419 for all 1200 data
REM 103 parameters refined using 0 restraints

END

WGHT      0.0317      0.1355

REM Highest difference peak  0.196,  deepest hole -0.161,  1-sigma level  0.036
Q1    1   0.5862  0.5864  0.5840  11.00000  0.05    0.20
Q2    1   0.7487  0.5552  0.5467  11.00000  0.05    0.16
Q3    1   0.9344  0.4960  0.5568  11.00000  0.05    0.13
Q4    1   1.0431  0.5747  0.5521  11.00000  0.05    0.13
Q5    1   0.8825  0.3982  0.6780  11.00000  0.05    0.12
;
_shelx_res_checksum              37964
_olex2_submission_special_instructions 'No special instructions were received'
