# 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_mo_jl24032_0m
_database_code_depnum_ccdc_archive 'CCDC 2404167'
loop_
_audit_author_name
_audit_author_address
'Susanna Vance'
;University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;
_audit_creation_date             2024-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 N2 O4'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4675(3)
_cell_length_b                   9.3690(4)
_cell_length_c                   14.5222(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.911(2)
_cell_angle_gamma                90
_cell_volume                     1014.71(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6432
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1106 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.9081.
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    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43046
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.424
_diffrn_reflns_theta_min         2.588
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1424
_reflns_number_total             1858
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.068
_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)+(0.0980P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1564
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4)
;
_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 0.7020(2) 0.58630(15) 0.27764(10) 0.0278(4) Uani 1 1 d . . . . .
H1 H 0.725649 0.672393 0.288893 0.042 Uiso 1 1 calc R U . . .
O2 O 0.5485(2) 0.16118(15) 0.42390(10) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.552674 0.120593 0.475537 0.043 Uiso 1 1 calc R U . . .
O3 O 0.8818(2) 0.93469(15) 0.38849(10) 0.0324(4) Uani 1 1 d . . . . .
H3 H 0.855024 0.981725 0.340503 0.049 Uiso 1 1 calc R U . . .
O4 O 0.5841(2) 0.06620(16) 0.67966(10) 0.0347(4) Uani 1 1 d . . . . .
H4 H 0.533489 -0.012594 0.669007 0.052 Uiso 1 1 calc R U . . .
N1 N 0.8215(2) 0.79413(17) 0.37698(12) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.5969(2) 0.14109(18) 0.59709(12) 0.0280(4) Uani 1 1 d . . . . .
C1 C 0.8317(3) 0.7193(2) 0.45152(14) 0.0243(5) Uani 1 1 d . . . . .
C2 C 0.6729(3) 0.2644(2) 0.60542(14) 0.0251(5) Uani 1 1 d . . . . .
C3 C 0.9005(3) 0.7782(2) 0.54276(14) 0.0292(5) Uani 1 1 d . . . . .
H3A H 0.969382 0.865360 0.532689 0.044 Uiso 1 1 calc R U . . .
H3B H 0.977892 0.707335 0.574516 0.044 Uiso 1 1 calc R U . . .
H3C H 0.799152 0.800365 0.580617 0.044 Uiso 1 1 calc R U . . .
C4 C 0.7455(3) 0.3235(2) 0.69562(14) 0.0303(5) Uani 1 1 d . . . . .
H4A H 0.674784 0.406934 0.712133 0.045 Uiso 1 1 calc R U . . .
H4B H 0.870869 0.351765 0.690114 0.045 Uiso 1 1 calc R U . . .
H4C H 0.738380 0.250484 0.743619 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7638(2) 0.5718(2) 0.44357(14) 0.0228(5) Uani 1 1 d . . . . .
C6 C 0.7530(2) 0.4859(2) 0.52153(14) 0.0232(5) Uani 1 1 d . . . . .
H6 H 0.795751 0.523813 0.579206 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6836(3) 0.3481(2) 0.52008(14) 0.0239(5) Uani 1 1 d . . . . .
C8 C 0.6209(3) 0.2936(2) 0.43269(14) 0.0243(5) Uani 1 1 d . . . . .
C9 C 0.6300(3) 0.3755(2) 0.35435(14) 0.0242(5) Uani 1 1 d . . . . .
H9 H 0.587356 0.337412 0.296684 0.029 Uiso 1 1 calc R U . . .
C10 C 0.7001(3) 0.5123(2) 0.35813(13) 0.0239(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 H1 0.8400 . ?
O1 C10 1.360(2) . ?
O2 H2 0.8400 . ?
O2 C8 1.357(2) . ?
O3 H3 0.8400 . ?
O3 N1 1.399(2) . ?
O4 H4 0.8400 . ?
O4 N2 1.397(2) . ?
N1 C1 1.289(3) . ?
N2 C2 1.290(3) . ?
C1 C3 1.502(3) . ?
C1 C5 1.474(3) . ?
C2 C4 1.498(3) . ?
C2 C7 1.472(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.395(3) . ?
C5 C10 1.420(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(3) . ?
C7 C8 1.425(3) . ?
C8 C9 1.376(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(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 O1 H1 109.5 . . ?
C8 O2 H2 109.5 . . ?
N1 O3 H3 109.5 . . ?
N2 O4 H4 109.5 . . ?
C1 N1 O3 114.03(16) . . ?
C2 N2 O4 114.74(17) . . ?
N1 C1 C3 122.94(18) . . ?
N1 C1 C5 116.04(18) . . ?
C5 C1 C3 120.96(17) . . ?
N2 C2 C4 123.44(19) . . ?
N2 C2 C7 116.14(18) . . ?
C7 C2 C4 120.41(18) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 120.74(18) . . ?
C6 C5 C10 116.90(18) . . ?
C10 C5 C1 122.32(18) . . ?
C5 C6 H6 118.0 . . ?
C7 C6 C5 124.07(18) . . ?
C7 C6 H6 118.0 . . ?
C6 C7 C2 121.19(18) . . ?
C6 C7 C8 116.83(18) . . ?
C8 C7 C2 121.97(18) . . ?
O2 C8 C7 121.52(18) . . ?
O2 C8 C9 117.89(18) . . ?
C9 C8 C7 120.59(19) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.15(19) . . ?
C10 C9 H9 119.4 . . ?
O1 C10 C5 122.27(18) . . ?
O1 C10 C9 117.26(18) . . ?
C9 C10 C5 120.46(18) . . ?

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
O1 H1 N1 0.84 1.83 2.557(2) 143.6 . yes
O2 H2 N2 0.84 1.79 2.530(2) 146.0 . yes
O3 H3 O1 0.84 2.00 2.842(2) 177.0 2_655 yes
O4 H4 O2 0.84 2.01 2.762(2) 148.2 3_656 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
O2 C8 C9 C10 179.21(17) . . . . ?
O3 N1 C1 C3 0.5(3) . . . . ?
O3 N1 C1 C5 177.94(15) . . . . ?
O4 N2 C2 C4 1.0(3) . . . . ?
O4 N2 C2 C7 -178.17(16) . . . . ?
N1 C1 C5 C6 -174.04(17) . . . . ?
N1 C1 C5 C10 3.4(3) . . . . ?
N2 C2 C7 C6 176.14(18) . . . . ?
N2 C2 C7 C8 -2.7(3) . . . . ?
C1 C5 C6 C7 177.19(18) . . . . ?
C1 C5 C10 O1 1.8(3) . . . . ?
C1 C5 C10 C9 -177.07(18) . . . . ?
C2 C7 C8 O2 -0.2(3) . . . . ?
C2 C7 C8 C9 178.88(18) . . . . ?
C3 C1 C5 C6 3.4(3) . . . . ?
C3 C1 C5 C10 -179.12(17) . . . . ?
C4 C2 C7 C6 -3.1(3) . . . . ?
C4 C2 C7 C8 178.10(18) . . . . ?
C5 C6 C7 C2 -178.72(18) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C5 C10 O1 179.31(17) . . . . ?
C6 C5 C10 C9 0.5(3) . . . . ?
C6 C7 C8 O2 -179.09(17) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 O1 -179.22(17) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
