# 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_20250409-gy-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2442633'
loop_
_audit_author_name
_audit_author_address
guanyu
;Hebei Normal University
China
;
_audit_update_record             
;
2025-04-10 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_audit_creation_date             2025-04-09
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   23.8084(4)
_cell_length_b                   4.61710(10)
_cell_length_c                   11.0799(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.314(2)
_cell_angle_gamma                90
_cell_volume                     1216.97(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9720
_cell_measurement_theta_min      3.7450
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.786
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.762
_diffrn_reflns_theta_min         3.716
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -20.00   0.50    1.18    --  -91.75  57.00-120.00   90
  2  ω    -47.00 -22.00   0.50    1.18    --  -91.75  57.00 -90.00   50
  3  ω    -54.00 -21.00   0.50    1.18    --  -91.75  57.00 -60.00   66
  4  ω    -64.00 -20.00   0.50    1.18    --  -91.75  57.00 150.00   88
  5  ω    -47.00 -22.00   0.50    1.18    --  -91.75  42.00  57.00   50
  6  ω   -145.00-119.00   0.50    1.18    --  -91.75 -42.00 -94.00   52
  7  ω   -119.00 -39.00   0.50    0.30    --  -47.34 -42.00 -94.00  160
  8  ω      1.00  28.00   0.50    0.30    --  -47.34  19.00-180.00   54
  9  ω    -46.00  11.00   0.50    0.30    --  -47.34  42.00  57.00  114
 10  ω     47.00 103.00   0.50    1.18    --  108.72 -99.00-180.00  112
 11  ω     48.00  74.00   0.50    1.18    --  108.72 -99.00 -30.00   52
 12  ω     37.00 105.00   0.50    1.18    --  108.72 -77.00 -90.00  136
 13  ω     40.00  65.00   0.50    1.18    --  108.72 -57.00-150.00   50
 14  ω     36.00  66.00   0.50    1.18    --  108.72 -57.00-180.00   60
 15  ω     38.00  64.00   0.50    1.18    --  108.72 -57.00 -90.00   52
 16  ω     37.00  62.00   0.50    1.18    --  108.72 -57.00 -30.00   50
 17  ω     36.00  61.00   0.50    1.18    --  108.72 -57.00   0.00   50
 18  ω    -26.00  25.00   0.50    0.30    --   47.34 -19.00 150.00  102
 19  ω     40.00  65.00   0.50    1.18    --  108.72 -57.00 150.00   50
 20  ω     38.00  64.00   0.50    1.18    --  108.72 -57.00  90.00   52
 21  ω      4.00  38.00   0.50    0.30    --   47.34 -42.00 -94.00   68
 22  ω     95.00 173.00   0.50    1.18    --  108.72  38.00   0.00  156
 23  ω    104.00 168.00   0.50    1.18    --  108.72  42.00  57.00  128
 24  ω     53.00  88.00   0.50    0.30    --   47.34  42.00  57.00   70
 25  ω     99.00 135.00   0.50    1.18    --  108.72  57.00 150.00   72
 26  ω    153.00 178.00   0.50    1.18    --  108.72  57.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0535819000
_diffrn_orient_matrix_UB_12      -0.1691960000
_diffrn_orient_matrix_UB_13      0.0383054000
_diffrn_orient_matrix_UB_21      0.0238259000
_diffrn_orient_matrix_UB_22      0.0547127000
_diffrn_orient_matrix_UB_23      -0.1251907000
_diffrn_orient_matrix_UB_31      0.0274798000
_diffrn_orient_matrix_UB_32      0.2823706000
_diffrn_orient_matrix_UB_33      0.0471183000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2114
_reflns_number_total             2447
_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 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.052
_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)+(0.0688P)²+0.1543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1249
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00F(H00E,H00F), C00G(H00G,H00H), C00H(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00D)
2.c X=CH2 refined with riding coordinates:
 C00I(H00K,H00L)
;
_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
O001 O 0.55228(4) 0.1887(3) 0.50853(10) 0.0706(3) Uani 1 1 d . . . . .
O002 O 0.90399(4) 1.1777(3) 0.76634(10) 0.0729(3) Uani 1 1 d . . . . .
O003 O 0.55932(4) 0.4625(3) 0.68253(10) 0.0758(4) Uani 1 1 d . . . . .
N004 N 0.84266(4) 0.8881(3) 0.67333(10) 0.0548(3) Uani 1 1 d . . . . .
O005 O 0.83175(6) 1.0103(3) 0.87166(10) 0.0912(4) Uani 1 1 d . . . . .
C006 C 0.60679(5) 0.4996(3) 0.61737(12) 0.0519(3) Uani 1 1 d . . . . .
C007 C 0.60250(5) 0.3367(3) 0.51346(12) 0.0509(3) Uani 1 1 d . . . . .
C008 C 0.69469(5) 0.6834(3) 0.56121(12) 0.0513(3) Uani 1 1 d . . . . .
C009 C 0.69016(6) 0.5160(3) 0.45774(12) 0.0565(3) Uani 1 1 d . . . . .
H009 H 0.719057 0.521602 0.403768 0.068 Uiso 1 1 calc R U . . .
C00A C 0.65178(6) 0.6748(3) 0.64387(13) 0.0565(3) Uani 1 1 d . . . . .
H00A H 0.653865 0.784467 0.714304 0.068 Uiso 1 1 calc R U . . .
C00B C 0.79295(5) 0.7091(3) 0.65240(13) 0.0549(3) Uani 1 1 d . . . . .
H00B H 0.779998 0.641618 0.729380 0.066 Uiso 1 1 calc R U . . .
H00C H 0.802828 0.540639 0.605436 0.066 Uiso 1 1 calc R U . . .
C00C C 0.64369(6) 0.3390(3) 0.43152(12) 0.0594(4) Uani 1 1 d . . . . .
H00D H 0.640985 0.227930 0.361496 0.071 Uiso 1 1 calc R U . . .
C00D C 0.85548(6) 1.0175(3) 0.77789(13) 0.0600(4) Uani 1 1 d . . . . .
C00E C 0.92184(6) 1.1503(3) 0.64960(14) 0.0615(4) Uani 1 1 d . . . . .
C00F C 0.88107(6) 0.9629(3) 0.58068(13) 0.0598(4) Uani 1 1 d . . . . .
H00E H 0.862248 1.067810 0.514866 0.072 Uiso 1 1 calc R U . . .
H00F H 0.899187 0.792455 0.548955 0.072 Uiso 1 1 calc R U . . .
C00G C 0.74569(6) 0.8712(3) 0.58624(15) 0.0625(4) Uani 1 1 d . . . . .
H00G H 0.735081 1.036430 0.634329 0.075 Uiso 1 1 calc R U . . .
H00H H 0.759002 0.943586 0.510339 0.075 Uiso 1 1 calc R U . . .
C00H C 0.52856(6) 0.2353(4) 0.62232(16) 0.0713(4) Uani 1 1 d . . . . .
H00I H 0.530841 0.059395 0.670149 0.086 Uiso 1 1 calc R U . . .
H00J H 0.489309 0.289171 0.611315 0.086 Uiso 1 1 calc R U . . .
C00I C 0.96785(8) 1.2781(5) 0.6152(2) 0.0911(6) Uani 1 1 d . . . . .
H00K H 0.989169 1.389904 0.669761 0.109 Uiso 1 1 calc R U . . .
H00L H 0.979080 1.256842 0.536251 0.109 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
O001 C007 1.3763(15) . ?
O001 C00H 1.419(2) . ?
O002 C00D 1.3817(17) . ?
O002 C00E 1.3834(19) . ?
O003 C006 1.3763(16) . ?
O003 C00H 1.429(2) . ?
N004 C00B 1.4544(16) . ?
N004 C00D 1.3282(19) . ?
N004 C00F 1.4440(17) . ?
O005 C00D 1.2030(19) . ?
C006 C007 1.3755(19) . ?
C006 C00A 1.3646(18) . ?
C007 C00C 1.3631(19) . ?
C008 C009 1.383(2) . ?
C008 C00A 1.400(2) . ?
C008 C00G 1.5086(17) . ?
C009 H009 0.9300 . ?
C009 C00C 1.3967(19) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B C00G 1.5155(19) . ?
C00C H00D 0.9300 . ?
C00E C00F 1.488(2) . ?
C00E C00I 1.314(2) . ?
C00F H00E 0.9700 . ?
C00F H00F 0.9700 . ?
C00G H00G 0.9700 . ?
C00G H00H 0.9700 . ?
C00H H00I 0.9700 . ?
C00H H00J 0.9700 . ?
C00I H00K 0.9300 . ?
C00I H00L 0.9300 . ?

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
C007 O001 C00H 105.43(11) . . ?
C00D O002 C00E 109.10(11) . . ?
C006 O003 C00H 105.23(11) . . ?
C00D N004 C00B 123.48(12) . . ?
C00D N004 C00F 112.50(11) . . ?
C00F N004 C00B 123.85(11) . . ?
C007 C006 O003 109.65(11) . . ?
C00A C006 O003 127.96(13) . . ?
C00A C006 C007 122.36(12) . . ?
C006 C007 O001 109.86(11) . . ?
C00C C007 O001 128.65(12) . . ?
C00C C007 C006 121.48(12) . . ?
C009 C008 C00A 119.47(12) . . ?
C009 C008 C00G 120.57(13) . . ?
C00A C008 C00G 119.96(13) . . ?
C008 C009 H009 118.9 . . ?
C008 C009 C00C 122.28(13) . . ?
C00C C009 H009 118.9 . . ?
C006 C00A C008 117.60(12) . . ?
C006 C00A H00A 121.2 . . ?
C008 C00A H00A 121.2 . . ?
N004 C00B H00B 109.1 . . ?
N004 C00B H00C 109.1 . . ?
N004 C00B C00G 112.34(11) . . ?
H00B C00B H00C 107.9 . . ?
C00G C00B H00B 109.1 . . ?
C00G C00B H00C 109.1 . . ?
C007 C00C C009 116.81(13) . . ?
C007 C00C H00D 121.6 . . ?
C009 C00C H00D 121.6 . . ?
N004 C00D O002 108.88(12) . . ?
O005 C00D O002 121.22(13) . . ?
O005 C00D N004 129.90(14) . . ?
O002 C00E C00F 108.32(11) . . ?
C00I C00E O002 121.41(16) . . ?
C00I C00E C00F 130.26(17) . . ?
N004 C00F C00E 101.12(11) . . ?
N004 C00F H00E 111.5 . . ?
N004 C00F H00F 111.5 . . ?
C00E C00F H00E 111.5 . . ?
C00E C00F H00F 111.5 . . ?
H00E C00F H00F 109.4 . . ?
C008 C00G C00B 112.43(11) . . ?
C008 C00G H00G 109.1 . . ?
C008 C00G H00H 109.1 . . ?
C00B C00G H00G 109.1 . . ?
C00B C00G H00H 109.1 . . ?
H00G C00G H00H 107.8 . . ?
O001 C00H O003 108.13(11) . . ?
O001 C00H H00I 110.1 . . ?
O001 C00H H00J 110.1 . . ?
O003 C00H H00I 110.1 . . ?
O003 C00H H00J 110.1 . . ?
H00I C00H H00J 108.4 . . ?
C00E C00I H00K 120.0 . . ?
C00E C00I H00L 120.0 . . ?
H00K C00I H00L 120.0 . . ?

_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 1.711
_oxdiff_exptl_absorpt_empirical_full_min 0.461
