# Supplementary Information (SI) for Journal of Materials Chemistry B.
# 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_161
_database_code_depnum_ccdc_archive 'CCDC 2410510'
loop_
_audit_author_name
_audit_author_address
'zhenyuan wang'
;Shenzhen Shinehigh Innovation Technology
China
;
_audit_update_record             
;
2024-12-16 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_audit_creation_date             2022-01-12
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H16 N O2, C2 H3 O3'
_chemical_formula_sum            'C10 H19 N O5'
_chemical_formula_weight         233.26
_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'
N N 0.0311 0.0180 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.4867(3)
_cell_length_b                   11.8536(3)
_cell_length_c                   21.3590(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2401.85(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      72.6240
_cell_measurement_theta_min      2.0990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70877
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5723
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.377
_diffrn_reflns_theta_min         4.140
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  31.00   1.00    1.00    --  -40.73  38.00 -90.00   95
  2  ω     10.00  60.00   1.00    1.00    --   40.73 -99.00  30.00   50
  3  ω    103.00 129.00   1.00    1.00    --  107.58 -30.00 -60.00   26
  4  ω     78.00 168.00   1.00    1.00    --  107.58  61.00 -90.00   90
  5  ω    105.00 132.00   1.00    1.00    --  107.58 112.00 -60.00   27
  6  ω    147.00 176.00   1.00    1.00    --  107.58 125.00  60.00   29
  7  ω    106.00 131.00   1.00    1.00    --  107.58 125.00  60.00   25
  8  ω      1.00  27.00   1.00    1.00    --   40.73 -99.00-180.00   26
  9  ω     25.00 106.00   1.00    1.00    --  107.58 -95.00-150.00   81
;
_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      -0.0467092000
_diffrn_orient_matrix_UB_12      0.0349454000
_diffrn_orient_matrix_UB_13      -0.0663067000
_diffrn_orient_matrix_UB_21      -0.1523483000
_diffrn_orient_matrix_UB_22      -0.0356176000
_diffrn_orient_matrix_UB_23      0.0153847000
_diffrn_orient_matrix_UB_31      -0.0315336000
_diffrn_orient_matrix_UB_32      0.1199766000
_diffrn_orient_matrix_UB_33      0.0238374000
_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                2086
_reflns_number_total             2365
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.048
_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)+(0.0583P)²+0.8414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5A)
;
_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 0.20485(16) 0.58929(13) 0.82304(6) 0.0548(4) Uani 1 1 d . . . . .
H1 H 0.187692 0.565242 0.858225 0.082 Uiso 1 1 calc R U . . .
O2 O 0.03826(14) 0.71170(11) 0.84842(6) 0.0473(3) Uani 1 1 d . . . . .
N1 N 0.06692(13) 0.83517(11) 0.51036(6) 0.0285(3) Uani 1 1 d . . . . .
H1A H 0.083471 0.877431 0.476710 0.034 Uiso 1 1 calc R U . . .
H1B H -0.025611 0.830272 0.516682 0.034 Uiso 1 1 calc R U . . .
H1C H 0.102234 0.766442 0.504397 0.034 Uiso 1 1 calc R U . . .
C1 C 0.12761(17) 0.67871(14) 0.81214(8) 0.0331(4) Uani 1 1 d . . . . .
C2 C 0.16015(16) 0.73158(13) 0.74957(8) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.262812 0.731599 0.744464 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1100(2) 0.85349(14) 0.74483(8) 0.0419(4) Uani 1 1 d . . . . .
H3A H 0.153720 0.898089 0.777597 0.050 Uiso 1 1 calc R U . . .
H3B H 0.008694 0.856501 0.750643 0.050 Uiso 1 1 calc R U . . .
C4 C 0.1482(2) 0.90253(14) 0.68105(8) 0.0404(4) Uani 1 1 d . . . . .
H4A H 0.111372 0.978701 0.678124 0.049 Uiso 1 1 calc R U . . .
H4B H 0.249956 0.906643 0.677405 0.049 Uiso 1 1 calc R U . . .
C5 C 0.09006(15) 0.83270(12) 0.62712(7) 0.0281(3) Uani 1 1 d . . . . .
H5 H -0.013092 0.834362 0.629399 0.034 Uiso 1 1 calc R U . . .
C6 C 0.13819(17) 0.70998(13) 0.63277(7) 0.0307(3) Uani 1 1 d . . . . .
H6A H 0.239656 0.706093 0.627598 0.037 Uiso 1 1 calc R U . . .
H6B H 0.095114 0.665623 0.599754 0.037 Uiso 1 1 calc R U . . .
C7 C 0.09764(17) 0.66049(12) 0.69645(7) 0.0308(3) Uani 1 1 d . . . . .
H7A H -0.004207 0.658646 0.700323 0.037 Uiso 1 1 calc R U . . .
H7B H 0.132298 0.583698 0.699526 0.037 Uiso 1 1 calc R U . . .
C8 C 0.13485(15) 0.88757(13) 0.56597(7) 0.0307(3) Uani 1 1 d . . . . .
H8A H 0.110853 0.967083 0.567237 0.037 Uiso 1 1 calc R U . . .
H8B H 0.236397 0.881660 0.561772 0.037 Uiso 1 1 calc R U . . .
O3 O 0.16586(10) 0.49557(8) 0.92892(5) 0.0280(3) Uani 1 1 d . . . . .
O4 O 0.23819(11) 0.34028(9) 0.97759(5) 0.0317(3) Uani 1 1 d . . . . .
O5 O 0.51159(11) 0.37281(11) 0.93962(6) 0.0399(3) Uani 1 1 d . . . . .
H5A H 0.504528 0.322332 0.913558 0.060 Uiso 1 1 calc R U . . .
C9 C 0.26090(14) 0.42616(12) 0.94625(6) 0.0231(3) Uani 1 1 d . . . . .
C10 C 0.41043(15) 0.45700(14) 0.92722(7) 0.0321(4) Uani 1 1 d . . . . .
H10A H 0.411446 0.473446 0.882735 0.039 Uiso 1 1 calc R U . . .
H10B H 0.437577 0.525312 0.949126 0.039 Uiso 1 1 calc R U . . .


_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 0.8200 . ?
O1 C1 1.309(2) . ?
O2 C1 1.213(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.487(2) . ?
C1 C2 1.508(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.525(2) . ?
C2 C7 1.533(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.525(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.522(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.529(2) . ?
C5 C8 1.520(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.530(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O3 C9 1.2755(17) . ?
O4 C9 1.2372(17) . ?
O5 H5A 0.8200 . ?
O5 C10 1.4097(19) . ?
C9 C10 1.5203(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
O1 C1 C2 112.30(14) . . ?
O2 C1 O1 122.57(16) . . ?
O2 C1 C2 125.11(15) . . ?
C1 C2 H2 107.6 . . ?
C1 C2 C3 112.88(14) . . ?
C1 C2 C7 110.39(13) . . ?
C3 C2 H2 107.6 . . ?
C3 C2 C7 110.57(13) . . ?
C7 C2 H2 107.6 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.29(15) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.52(14) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5 108.3 . . ?
C4 C5 C6 110.46(13) . . ?
C4 C5 C8 108.45(13) . . ?
C6 C5 H5 108.3 . . ?
C8 C5 H5 108.3 . . ?
C8 C5 C6 113.04(13) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.08(13) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C2 C7 C6 110.48(13) . . ?
C2 C7 H7A 109.6 . . ?
C2 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C5 112.74(12) . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C5 C8 H8A 109.0 . . ?
C5 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 O5 H5A 109.5 . . ?
O3 C9 C10 115.26(12) . . ?
O4 C9 O3 124.39(13) . . ?
O4 C9 C10 120.33(13) . . ?
O5 C10 C9 114.50(13) . . ?
O5 C10 H10A 108.6 . . ?
O5 C10 H10B 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?

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 -161.01(15) . . . . ?
O1 C1 C2 C7 74.68(18) . . . . ?
O2 C1 C2 C3 20.8(2) . . . . ?
O2 C1 C2 C7 -103.53(19) . . . . ?
C1 C2 C3 C4 179.06(14) . . . . ?
C1 C2 C7 C6 -176.53(13) . . . . ?
C2 C3 C4 C5 56.0(2) . . . . ?
C3 C2 C7 C6 57.84(18) . . . . ?
C3 C4 C5 C6 -55.02(19) . . . . ?
C3 C4 C5 C8 -179.41(14) . . . . ?
C4 C5 C6 C7 55.21(17) . . . . ?
C4 C5 C8 N1 -171.97(13) . . . . ?
C5 C6 C7 C2 -57.09(17) . . . . ?
C6 C5 C8 N1 65.19(16) . . . . ?
C7 C2 C3 C4 -56.73(19) . . . . ?
C8 C5 C6 C7 176.92(13) . . . . ?
O3 C9 C10 O5 -172.27(12) . . . . ?
O4 C9 C10 O5 9.3(2) . . . . ?

_olex2_date_sample_data_collection 2022-01-12
_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.639
