# 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. 
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#######################################################################

data_small61_1_0f
_database_code_depnum_ccdc_archive 'CCDC 2375035'
loop_
_audit_author_name
_audit_author_address
'Dr. Sizwe Zamisa'
;University of KwaZulu Natal
South Africa
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;
_audit_creation_date             2024-05-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   6.8069(15)
_cell_length_b                   18.566(5)
_cell_length_c                   20.810(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2630.0(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1319
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      19.48
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6087
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1273 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.8168.
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    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 0.00 1.00 0.0750
-2.00 1.00 0.00 0.0640
0.00 1.00 2.00 0.0260
0.00 -1.00 0.00 0.0290
0.00 1.00 0.00 0.0220
0.00 -2.00 1.00 0.0380
0.00 1.00 1.00 0.0170
0.00 0.00 -1.00 0.0010
1.00 0.00 0.00 0.0250
1.00 -1.00 -2.00 0.0230
2.00 1.00 -1.00 0.0240
2.00 -2.00 1.00 0.0360

_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19512
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.194
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                903
_reflns_number_total             1264
_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    ?
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1264
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.153
_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)+(0.0395P)²+6.0406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim C13 \\sim C14 \\sim C15 \\sim C16: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 N1, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O3(0.5) O4(0.5) C10(0.5) H10A(0.5) H10B(0.5) C11(0.5) H11A(0.5)
 H11B(0.5) C12(0.5) H12(0.5) N1(0.5) C13(0.5) C14(0.5) H14A(0.5) H14B(0.5)
 C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16A(0.5) H16B(0.5)
5.a Ternary CH refined with riding coordinates:
 C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.500000 0.32875(16) 0.17330(13) 0.0488(9) Uani 1 2 d S T P A .
O2 O 0.500000 0.21258(19) 0.19290(16) 0.0675(12) Uani 1 2 d S T P A .
C1 C 0.500000 0.3573(2) 0.3038(2) 0.0510(14) Uani 1 2 d S T P . .
C2 C 0.500000 0.4162(2) 0.2590(2) 0.0462(12) Uani 1 2 d S T P A .
C3 C 0.500000 0.4886(3) 0.2764(2) 0.0607(16) Uani 1 2 d S T P . .
H3 H 0.500000 0.501567 0.320512 0.073 Uiso 1 2 calc R U P A .
C4 C 0.500000 0.5412(3) 0.2302(2) 0.0684(18) Uani 1 2 d S T P A .
H4 H 0.500000 0.590491 0.242400 0.082 Uiso 1 2 calc R U P . .
C5 C 0.500000 0.5225(3) 0.1663(2) 0.0581(14) Uani 1 2 d S T P . .
H5 H 0.500000 0.559425 0.134606 0.070 Uiso 1 2 calc R U P A .
C6 C 0.500000 0.4520(3) 0.1472(2) 0.0466(12) Uani 1 2 d S T P A .
H6 H 0.500000 0.439408 0.102989 0.056 Uiso 1 2 calc R U P . .
C7 C 0.500000 0.3999(2) 0.1940(2) 0.0453(12) Uani 1 2 d S T P . .
C8 C 0.500000 0.2725(3) 0.2165(2) 0.0560(14) Uani 1 2 d S T P . .
C9 C 0.500000 0.2882(2) 0.2836(2) 0.0490(13) Uani 1 2 d S T P A .
O3 O 0.533(3) 0.37787(19) 0.36565(16) 0.045(5) Uani 0.5 1 d . . P A -1
O4 O 0.8525(9) 0.3803(3) 0.4971(2) 0.0672(15) Uani 0.5 1 d . . P A -1
C10 C 0.513(9) 0.2263(3) 0.3302(3) 0.054(4) Uani 0.5 1 d . . P A -1
H10A H 0.649401 0.207672 0.331992 0.065 Uiso 0.5 1 calc R U P A -1
H10B H 0.425153 0.186697 0.316631 0.065 Uiso 0.5 1 calc R U P A -1
C11 C 0.4509(12) 0.2551(3) 0.3963(3) 0.049(3) Uani 0.5 1 d . . P A -1
H11A H 0.310051 0.268469 0.395564 0.059 Uiso 0.5 1 calc R U P A -1
H11B H 0.470033 0.217522 0.429414 0.059 Uiso 0.5 1 calc R U P A -1
C12 C 0.5743(10) 0.3205(3) 0.4121(3) 0.0430(18) Uani 0.5 1 d . . P A -1
H12 H 0.716669 0.307324 0.410047 0.052 Uiso 0.5 1 calc R U P A -1
N1 N 0.532(3) 0.3510(3) 0.4731(2) 0.048(4) Uani 0.5 1 d . U P A -1
C13 C 0.678(3) 0.3818(7) 0.5106(6) 0.049(3) Uani 0.5 1 d . U P A -1
C14 C 0.582(4) 0.4115(14) 0.5697(9) 0.065(5) Uani 0.5 1 d . U P A -1
H14A H 0.619064 0.382975 0.608079 0.078 Uiso 0.5 1 calc R U P A -1
H14B H 0.620940 0.462288 0.576651 0.078 Uiso 0.5 1 calc R U P A -1
C15 C 0.370(4) 0.4056(15) 0.5566(10) 0.070(4) Uani 0.5 1 d . U P A -1
H15A H 0.313113 0.454144 0.549727 0.084 Uiso 0.5 1 calc R U P A -1
H15B H 0.302263 0.383263 0.593734 0.084 Uiso 0.5 1 calc R U P A -1
C16 C 0.340(3) 0.3603(9) 0.4977(8) 0.067(5) Uani 0.5 1 d . U P A -1
H16A H 0.280023 0.313345 0.508855 0.081 Uiso 0.5 1 calc R U P A -1
H16B H 0.254727 0.385207 0.466197 0.081 Uiso 0.5 1 calc R U P A -1


_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 C7 1.389(5) . ?
O1 C8 1.379(6) . ?
O2 C8 1.216(6) . ?
C1 C2 1.436(6) . ?
C1 C9 1.351(6) . ?
C1 O3 1.361(7) . ?
C2 C3 1.392(6) . ?
C2 C7 1.386(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(6) . ?
C8 C9 1.427(6) . ?
C9 C10 1.506(8) . ?
O3 C12 1.466(8) . ?
O4 C13 1.223(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.536(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.512(9) . ?
C12 H12 1.0000 . ?
C12 N1 1.419(8) . ?
N1 C13 1.386(16) . ?
N1 C16 1.41(2) . ?
C13 C14 1.495(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.478(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.500(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C8 O1 C7 121.2(3) . . ?
C9 C1 C2 121.4(4) . . ?
C9 C1 O3 124.0(4) . . ?
O3 C1 C2 113.6(4) . . ?
C3 C2 C1 124.5(4) . . ?
C7 C2 C1 117.9(4) . . ?
C7 C2 C3 117.6(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 121.0 . . ?
C5 C6 C7 118.0(4) . . ?
C7 C6 H6 121.0 . . ?
C2 C7 O1 120.6(4) . . ?
C6 C7 O1 116.8(4) . . ?
C6 C7 C2 122.6(4) . . ?
O1 C8 C9 118.9(4) . . ?
O2 C8 O1 115.4(4) . . ?
O2 C8 C9 125.6(5) . . ?
C1 C9 C8 119.9(4) . . ?
C1 C9 C10 121.7(4) . . ?
C8 C9 C10 118.3(4) . . ?
C1 O3 C12 116.9(4) . . ?
C9 C10 H10A 110.3 . . ?
C9 C10 H10B 110.3 . . ?
C9 C10 C11 107.1(12) . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C10 108.7(16) . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
O3 C12 C11 109.5(7) . . ?
O3 C12 H12 109.5 . . ?
C11 C12 H12 109.5 . . ?
N1 C12 O3 105.1(5) . . ?
N1 C12 C11 113.7(7) . . ?
N1 C12 H12 109.5 . . ?
C13 N1 C12 121.5(13) . . ?
C13 N1 C16 114.0(7) . . ?
C16 N1 C12 124.1(13) . . ?
O4 C13 N1 123.9(12) . . ?
O4 C13 C14 128.2(14) . . ?
N1 C13 C14 107.8(15) . . ?
C13 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 C13 104(2) . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
C14 C15 C16 109(2) . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
N1 C16 C15 103.9(15) . . ?
N1 C16 H16A 111.0 . . ?
N1 C16 H16B 111.0 . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?

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 C8 C9 C1 0.000(1) . . . . ?
O1 C8 C9 C10 -176(3) . . . . ?
O2 C8 C9 C1 180.000(1) . . . . ?
O2 C8 C9 C10 4(3) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C1 C2 C7 O1 0.000(1) . . . . ?
C1 C2 C7 C6 180.000(1) . . . . ?
C1 C9 C10 C11 20(4) . . . . ?
C1 O3 C12 C11 -36.7(18) . . . . ?
C1 O3 C12 N1 -159.2(15) . . . . ?
C2 C1 C9 C8 0.000(1) . . . . ?
C2 C1 C9 C10 176(3) . . . . ?
C2 C1 O3 C12 -168.3(10) . . . . ?
C2 C3 C4 C5 0.000(2) . . . . ?
C3 C2 C7 O1 180.000(1) . . . . ?
C3 C2 C7 C6 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C5 C6 C7 O1 180.000(1) . . . . ?
C5 C6 C7 C2 0.000(1) . . . . ?
C7 O1 C8 O2 180.000(1) . . . . ?
C7 O1 C8 C9 0.000(1) . . . . ?
C7 C2 C3 C4 0.000(1) . . . . ?
C8 O1 C7 C2 0.000(1) . . . . ?
C8 O1 C7 C6 180.000(1) . . . . ?
C8 C9 C10 C11 -163.9(17) . . . . ?
C9 C1 C2 C3 180.000(1) . . . . ?
C9 C1 C2 C7 0.000(1) . . . . ?
C9 C1 O3 C12 1(2) . . . . ?
C9 C10 C11 C12 -54(4) . . . . ?
O3 C1 C2 C3 -10.5(10) . . . . ?
O3 C1 C2 C7 169.5(10) . . . . ?
O3 C1 C9 C8 -168.4(11) . . . . ?
O3 C1 C9 C10 8(3) . . . . ?
O3 C12 N1 C13 -95.1(12) . . . . ?
O3 C12 N1 C16 77.6(14) . . . . ?
O4 C13 C14 C15 174(2) . . . . ?
C10 C11 C12 O3 64.0(19) . . . . ?
C10 C11 C12 N1 -178.8(18) . . . . ?
C11 C12 N1 C13 145.2(8) . . . . ?
C11 C12 N1 C16 -42.1(13) . . . . ?
C12 N1 C13 O4 -5.7(16) . . . . ?
C12 N1 C13 C14 177.4(12) . . . . ?
C12 N1 C16 C15 -170.3(12) . . . . ?
N1 C13 C14 C15 -9(3) . . . . ?
C13 N1 C16 C15 2.9(15) . . . . ?
C13 C14 C15 C16 11(3) . . . . ?
C14 C15 C16 N1 -9(3) . . . . ?
C16 N1 C13 O4 -179.1(17) . . . . ?
C16 N1 C13 C14 4.1(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
