# 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_P21n
_database_code_depnum_ccdc_archive 'CCDC 2368736'
loop_
_audit_author_name
_audit_author_address
HuangWei
;Nanjing University of Science and Technology 
China
;
_audit_update_record             
;
2024-07-08 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V118 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C8 H8 N10 O'
_chemical_formula_moiety         ?
_chemical_formula_weight         260.24
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_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.
;

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                   3.616(2)
_cell_length_b                   16.677(11)
_cell_length_c                   17.954(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.76(2)
_cell_angle_gamma                90
_cell_volume                     1077.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    335
_cell_measurement_theta_min      20.499
_cell_measurement_theta_max      56.7405
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5074
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            7126
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_av_R_equivalents  0.1214
_diffrn_reflns_theta_min         3.626
_diffrn_reflns_theta_max         64.240
_diffrn_reflns_theta_full        64.240
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1779
_reflns_number_gt                999
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       
'Bruker BIS 8.5.0.27 Release/2023-03-20 && APEX5 2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1081P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1779
_refine_ls_number_parameters     190
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2104
_refine_ls_wR_factor_gt          0.1773
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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
C1_1 C 0.7321(12) 0.5179(3) 0.1415(2) 0.0375(12) Uani 1 1 d . . . . .
C2_1 C 0.9150(12) 0.4779(3) 0.2022(2) 0.0377(11) Uani 1 1 d D . . . .
C3_1 C 0.7004(13) 0.4602(3) 0.0834(3) 0.0406(12) Uani 1 1 d . . . . .
C4_1 C 0.6238(13) 0.5983(3) 0.1439(2) 0.0383(12) Uani 1 1 d . . . . .
N1_1 N 0.9703(10) 0.4020(2) 0.1789(2) 0.0414(11) Uani 1 1 d . . . . .
H1_1 H 1.077487 0.364389 0.207903 0.050 Uiso 1 1 calc R U . . .
N2_1 N 0.8430(10) 0.3901(2) 0.1062(2) 0.0412(10) Uani 1 1 d . . . . .
N3_1 N 0.5450(12) 0.6647(3) 0.1502(2) 0.0471(11) Uani 1 1 d . . . . .
N4_1 N 1.0313(12) 0.5038(3) 0.2707(2) 0.0462(11) Uani 1 1 d D . . . .
H4A_1 H 0.935(15) 0.548(2) 0.290(2) 0.069 Uiso 1 1 d D U . . .
H4B_1 H 1.142(15) 0.470(2) 0.3049(19) 0.069 Uiso 1 1 d D U . . .
N5_1 N 0.5538(10) 0.4648(2) 0.0088(2) 0.0391(10) Uani 1 1 d . . . . .
C1_2 C 0.2868(12) 0.3547(3) 0.5135(2) 0.0392(12) Uani 1 1 d . . . . .
C2_2 C 0.2025(12) 0.4176(3) 0.4612(3) 0.0403(12) Uani 1 1 d . . . . .
C3_2 C 0.4437(12) 0.2948(3) 0.4733(3) 0.0396(12) Uani 1 1 d D . . . .
C4_2 C 0.2242(12) 0.3480(3) 0.5889(3) 0.0423(12) Uani 1 1 d . . . . .
N1_2 N 0.3029(11) 0.3986(2) 0.3950(2) 0.0427(11) Uani 1 1 d . . . . .
N2_2 N 0.4466(11) 0.3236(2) 0.4034(2) 0.0413(11) Uani 1 1 d . . . . .
H2_2 H 0.533130 0.296570 0.366776 0.050 Uiso 1 1 calc R U . . .
N3_2 N 0.1797(12) 0.3378(3) 0.6510(3) 0.0498(11) Uani 1 1 d . . . . .
N4_2 N 0.0438(10) 0.4931(2) 0.4675(2) 0.0399(10) Uani 1 1 d . . . . .
N5_2 N 0.5765(12) 0.2226(2) 0.4949(2) 0.0446(11) Uani 1 1 d D . . . .
H5A_2 H 0.506(15) 0.197(2) 0.5354(19) 0.067 Uiso 1 1 d D U . . .
H5B_2 H 0.658(15) 0.188(2) 0.462(2) 0.067 Uiso 1 1 d D U . . .
O1_3 O 0.3301(10) 0.2705(2) 0.2511(2) 0.0453(9) Uani 1 1 d D . . . .
H1A_3 H 0.442(13) 0.248(3) 0.217(2) 0.068 Uiso 1 1 d D U . . .
H1B_3 H 0.206(13) 0.233(2) 0.269(3) 0.068 Uiso 1 1 d D U . . .


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
C1_1 C2_1 1.388(6) . ?
C1_1 C4_1 1.399(7) . ?
C1_1 C3_1 1.415(7) . ?
C2_1 N4_1 1.332(6) . ?
C2_1 N1_1 1.354(6) . ?
C3_1 N2_1 1.326(6) . ?
C3_1 N5_1 1.392(6) . ?
C4_1 N3_1 1.152(6) . ?
N1_1 N2_1 1.354(5) . ?
N1_1 H1_1 0.8800 . ?
N4_1 H4A_1 0.900(18) . ?
N4_1 H4B_1 0.896(18) . ?
N5_1 N5_1 1.267(7) 3_665 ?
C1_2 C3_2 1.387(7) . ?
C1_2 C4_2 1.398(7) . ?
C1_2 C2_2 1.422(7) . ?
C2_2 N1_2 1.316(6) . ?
C2_2 N4_2 1.393(6) . ?
C3_2 N5_2 1.339(6) . ?
C3_2 N2_2 1.345(6) . ?
C4_2 N3_2 1.155(6) . ?
N1_2 N2_2 1.356(5) . ?
N2_2 H2_2 0.8800 . ?
N4_2 N4_2 1.261(8) 3_566 ?
N5_2 H5A_2 0.899(18) . ?
N5_2 H5B_2 0.901(18) . ?
O1_3 H1A_3 0.850(10) . ?
O1_3 H1B_3 0.849(10) . ?

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
C2_1 C1_1 C4_1 123.3(4) . . ?
C2_1 C1_1 C3_1 104.4(4) . . ?
C4_1 C1_1 C3_1 132.2(4) . . ?
N4_1 C2_1 N1_1 123.1(4) . . ?
N4_1 C2_1 C1_1 130.6(5) . . ?
N1_1 C2_1 C1_1 106.3(4) . . ?
N2_1 C3_1 N5_1 116.4(4) . . ?
N2_1 C3_1 C1_1 111.8(4) . . ?
N5_1 C3_1 C1_1 131.8(4) . . ?
N3_1 C4_1 C1_1 175.9(5) . . ?
C2_1 N1_1 N2_1 112.8(4) . . ?
C2_1 N1_1 H1_1 123.6 . . ?
N2_1 N1_1 H1_1 123.6 . . ?
C3_1 N2_1 N1_1 104.6(4) . . ?
C2_1 N4_1 H4A_1 122(3) . . ?
C2_1 N4_1 H4B_1 120(3) . . ?
H4A_1 N4_1 H4B_1 114(3) . . ?
N5_1 N5_1 C3_1 111.6(5) 3_665 . ?
C3_2 C1_2 C4_2 124.1(4) . . ?
C3_2 C1_2 C2_2 105.0(4) . . ?
C4_2 C1_2 C2_2 130.8(5) . . ?
N1_2 C2_2 N4_2 116.4(4) . . ?
N1_2 C2_2 C1_2 111.0(4) . . ?
N4_2 C2_2 C1_2 132.5(5) . . ?
N5_2 C3_2 N2_2 123.8(4) . . ?
N5_2 C3_2 C1_2 130.5(4) . . ?
N2_2 C3_2 C1_2 105.7(4) . . ?
N3_2 C4_2 C1_2 175.9(5) . . ?
C2_2 N1_2 N2_2 105.0(4) . . ?
C3_2 N2_2 N1_2 113.2(4) . . ?
C3_2 N2_2 H2_2 123.4 . . ?
N1_2 N2_2 H2_2 123.4 . . ?
N4_2 N4_2 C2_2 112.6(5) 3_566 . ?
C3_2 N5_2 H5A_2 122(3) . . ?
C3_2 N5_2 H5B_2 121(3) . . ?
H5A_2 N5_2 H5B_2 112(3) . . ?
H1A_3 O1_3 H1B_3 104.1(17) . . ?

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
C4_1 C1_1 C2_1 N4_1 -1.9(8) . . . . ?
C3_1 C1_1 C2_1 N4_1 177.0(5) . . . . ?
C4_1 C1_1 C2_1 N1_1 179.5(4) . . . . ?
C3_1 C1_1 C2_1 N1_1 -1.5(5) . . . . ?
C2_1 C1_1 C3_1 N2_1 1.3(5) . . . . ?
C4_1 C1_1 C3_1 N2_1 -179.9(5) . . . . ?
C2_1 C1_1 C3_1 N5_1 -177.9(5) . . . . ?
C4_1 C1_1 C3_1 N5_1 0.9(9) . . . . ?
N4_1 C2_1 N1_1 N2_1 -177.3(4) . . . . ?
C1_1 C2_1 N1_1 N2_1 1.4(5) . . . . ?
N5_1 C3_1 N2_1 N1_1 178.9(4) . . . . ?
C1_1 C3_1 N2_1 N1_1 -0.4(5) . . . . ?
C2_1 N1_1 N2_1 C3_1 -0.6(5) . . . . ?
N2_1 C3_1 N5_1 N5_1 -175.8(5) . . . 3_665 ?
C1_1 C3_1 N5_1 N5_1 3.3(8) . . . 3_665 ?
C3_2 C1_2 C2_2 N1_2 -0.8(5) . . . . ?
C4_2 C1_2 C2_2 N1_2 -178.7(4) . . . . ?
C3_2 C1_2 C2_2 N4_2 -179.7(4) . . . . ?
C4_2 C1_2 C2_2 N4_2 2.3(8) . . . . ?
C4_2 C1_2 C3_2 N5_2 -2.5(8) . . . . ?
C2_2 C1_2 C3_2 N5_2 179.4(5) . . . . ?
C4_2 C1_2 C3_2 N2_2 178.4(4) . . . . ?
C2_2 C1_2 C3_2 N2_2 0.3(5) . . . . ?
N4_2 C2_2 N1_2 N2_2 180.0(3) . . . . ?
C1_2 C2_2 N1_2 N2_2 0.8(5) . . . . ?
N5_2 C3_2 N2_2 N1_2 -179.0(4) . . . . ?
C1_2 C3_2 N2_2 N1_2 0.2(5) . . . . ?
C2_2 N1_2 N2_2 C3_2 -0.6(5) . . . . ?
N1_2 C2_2 N4_2 N4_2 -179.8(5) . . . 3_566 ?
C1_2 C2_2 N4_2 N4_2 -0.9(8) . . . 3_566 ?

