# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_20220304fxj_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2ns8k9
_database_code_depnum_ccdc_archive 'CCDC 2466191'
loop_
_audit_author_name
_audit_author_address
'Xue-Ju Fu'
;Chengdu university of TCM
China
;
_audit_update_record             
;
2025-06-22 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 O2'
_chemical_formula_weight         331.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   6.9335(4)
_cell_length_b                   15.0785(7)
_cell_length_c                   8.7254(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.786(4)
_cell_angle_gamma                90
_cell_volume                     892.98(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4611
_cell_measurement_theta_min      5.18
_cell_measurement_theta_max      67.55

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9432
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.178
_diffrn_reflns_theta_max         68.569
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3188
_reflns_number_gt                2362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.954

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0651P)²+0.2490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(2)
_chemical_absolute_configuration UNK
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0701(6) 0.4132(2) 0.6057(4) 0.0680(9) Uani 1 1 d . . . . .
O002 O 0.2502(6) 0.3220(2) 0.4916(5) 0.0812(11) Uani 1 1 d . . . . .
N003 N 0.3073(6) 0.5578(2) 0.5692(5) 0.0572(10) Uani 1 1 d . . . . .
N004 N 0.4415(7) 0.7023(3) 0.5618(5) 0.0716(12) Uani 1 1 d . . . . .
H00A H 0.381124 0.720520 0.632788 0.086 Uiso 1 1 calc R U . . .
H00B H 0.514898 0.738242 0.522678 0.086 Uiso 1 1 calc R U . . .
C005 C 0.2131(8) 0.3962(3) 0.5298(5) 0.0591(12) Uani 1 1 d . . . . .
C006 C 0.3137(7) 0.4753(3) 0.4932(6) 0.0557(11) Uani 1 1 d . . . . .
C007 C 0.4346(7) 0.4853(3) 0.3869(5) 0.0543(11) Uani 1 1 d . . . . .
C008 C 0.5042(7) 0.5741(3) 0.3984(5) 0.0576(11) Uani 1 1 d . . . . .
C009 C 0.4819(7) 0.4195(3) 0.2746(5) 0.0549(11) Uani 1 1 d . . . . .
C00A C 0.6235(8) 0.6155(3) 0.3068(6) 0.0623(12) Uani 1 1 d . . . . .
C00B C 0.2093(7) 0.5792(3) 0.6953(5) 0.0557(11) Uani 1 1 d . . . . .
N00C N 0.7237(8) 0.6479(3) 0.2317(6) 0.0878(15) Uani 1 1 d . . . . .
C00D C 0.2943(8) 0.5557(3) 0.8462(6) 0.0681(13) Uani 1 1 d . . . . .
H00D H 0.415108 0.526571 0.867908 0.082 Uiso 1 1 calc R U . . .
C00E C 0.4211(7) 0.6175(3) 0.5119(6) 0.0567(11) Uani 1 1 d . . . . .
C00F C 0.3341(8) 0.3738(3) 0.1745(6) 0.0641(13) Uani 1 1 d . . . . .
H00F H 0.203041 0.383463 0.179475 0.077 Uiso 1 1 calc R U . . .
C00G C 0.6755(8) 0.4047(3) 0.2634(6) 0.0671(13) Uani 1 1 d . . . . .
H00G H 0.776663 0.435797 0.327576 0.081 Uiso 1 1 calc R U . . .
C00H C 0.0351(8) 0.6244(4) 0.6633(6) 0.0682(13) Uani 1 1 d . . . . .
H00H H -0.019229 0.641645 0.561279 0.082 Uiso 1 1 calc R U . . .
C00I C 0.1963(10) 0.5762(4) 0.9660(7) 0.0839(17) Uani 1 1 d . . . . .
H00I H 0.251090 0.560055 1.068472 0.101 Uiso 1 1 calc R U . . .
C00J C 0.3800(11) 0.3138(4) 0.0673(6) 0.0788(16) Uani 1 1 d . . . . .
H00J H 0.279546 0.283992 -0.000035 0.095 Uiso 1 1 calc R U . . .
C00K C -0.0333(9) 0.3375(4) 0.6530(7) 0.0778(16) Uani 1 1 d . . . . .
H00C H 0.058374 0.298179 0.719486 0.093 Uiso 1 1 calc R U . . .
H00E H -0.099556 0.304478 0.561958 0.093 Uiso 1 1 calc R U . . .
C00L C -0.0597(9) 0.6444(4) 0.7836(8) 0.0842(17) Uani 1 1 d . . . . .
H00L H -0.178992 0.674772 0.762086 0.101 Uiso 1 1 calc R U . . .
C00M C 0.0203(10) 0.6200(4) 0.9338(7) 0.0819(17) Uani 1 1 d . . . . .
H00M H -0.045033 0.633149 1.014110 0.098 Uiso 1 1 calc R U . . .
C00N C 0.5718(13) 0.2981(4) 0.0597(7) 0.0857(19) Uani 1 1 d . . . . .
H00N H 0.601791 0.256669 -0.010850 0.103 Uiso 1 1 calc R U . . .
C00O C 0.7193(11) 0.3431(4) 0.1558(8) 0.0831(18) Uani 1 1 d . . . . .
H00O H 0.849748 0.332815 0.149579 0.100 Uiso 1 1 calc R U . . .
C00P C -0.1807(12) 0.3738(6) 0.7411(10) 0.115(3) Uani 1 1 d . . . . .
H00K H -0.256342 0.419754 0.680397 0.173 Uiso 1 1 calc R U . . .
H00P H -0.112830 0.397816 0.839266 0.173 Uiso 1 1 calc R U . . .
H00Q H -0.267130 0.327139 0.759850 0.173 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 C005 1.324(6) . ?
O001 C00K 1.452(6) . ?
O002 C005 1.210(6) . ?
N003 C00E 1.358(6) . ?
N003 C006 1.416(6) . ?
N003 C00B 1.442(6) . ?
N004 C00E 1.349(6) . ?
N004 H00A 0.8600 . ?
N004 H00B 0.8600 . ?
C005 C006 1.449(7) . ?
C006 C007 1.379(7) . ?
C007 C008 1.420(6) . ?
C007 C009 1.477(6) . ?
C008 C00E 1.405(6) . ?
C008 C00A 1.408(7) . ?
C009 C00G 1.384(7) . ?
C009 C00F 1.387(7) . ?
C00A N00C 1.156(6) . ?
C00B C00H 1.366(6) . ?
C00B C00D 1.375(7) . ?
C00D C00I 1.393(8) . ?
C00D H00D 0.9300 . ?
C00F C00J 1.384(7) . ?
C00F H00F 0.9300 . ?
C00G C00O 1.397(8) . ?
C00G H00G 0.9300 . ?
C00H C00L 1.381(7) . ?
C00H H00H 0.9300 . ?
C00I C00M 1.365(9) . ?
C00I H00I 0.9300 . ?
C00J C00N 1.366(9) . ?
C00J H00J 0.9300 . ?
C00K C00P 1.502(9) . ?
C00K H00C 0.9700 . ?
C00K H00E 0.9700 . ?
C00L C00M 1.366(9) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N C00O 1.364(10) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00K 0.9600 . ?
C00P H00P 0.9600 . ?
C00P H00Q 0.9600 . ?

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
C005 O001 C00K 117.0(4) . . ?
C00E N003 C006 109.5(4) . . ?
C00E N003 C00B 122.2(4) . . ?
C006 N003 C00B 128.2(4) . . ?
C00E N004 H00A 120.0 . . ?
C00E N004 H00B 120.0 . . ?
H00A N004 H00B 120.0 . . ?
O002 C005 O001 122.6(4) . . ?
O002 C005 C006 124.1(4) . . ?
O001 C005 C006 113.3(4) . . ?
C007 C006 N003 107.5(4) . . ?
C007 C006 C005 128.6(4) . . ?
N003 C006 C005 123.9(4) . . ?
C006 C007 C008 107.5(4) . . ?
C006 C007 C009 128.3(4) . . ?
C008 C007 C009 124.2(4) . . ?
C00E C008 C00A 124.5(4) . . ?
C00E C008 C007 107.9(4) . . ?
C00A C008 C007 127.5(4) . . ?
C00G C009 C00F 118.5(4) . . ?
C00G C009 C007 120.3(4) . . ?
C00F C009 C007 121.1(4) . . ?
N00C C00A C008 178.7(6) . . ?
C00H C00B C00D 120.8(5) . . ?
C00H C00B N003 119.4(4) . . ?
C00D C00B N003 119.8(4) . . ?
C00B C00D C00I 118.8(5) . . ?
C00B C00D H00D 120.6 . . ?
C00I C00D H00D 120.6 . . ?
N004 C00E N003 122.7(4) . . ?
N004 C00E C008 129.6(4) . . ?
N003 C00E C008 107.7(4) . . ?
C00J C00F C009 120.6(5) . . ?
C00J C00F H00F 119.7 . . ?
C009 C00F H00F 119.7 . . ?
C009 C00G C00O 120.1(5) . . ?
C009 C00G H00G 119.9 . . ?
C00O C00G H00G 119.9 . . ?
C00B C00H C00L 119.5(5) . . ?
C00B C00H H00H 120.2 . . ?
C00L C00H H00H 120.2 . . ?
C00M C00I C00D 120.4(5) . . ?
C00M C00I H00I 119.8 . . ?
C00D C00I H00I 119.8 . . ?
C00N C00J C00F 120.4(6) . . ?
C00N C00J H00J 119.8 . . ?
C00F C00J H00J 119.8 . . ?
O001 C00K C00P 106.6(5) . . ?
O001 C00K H00C 110.4 . . ?
C00P C00K H00C 110.4 . . ?
O001 C00K H00E 110.4 . . ?
C00P C00K H00E 110.4 . . ?
H00C C00K H00E 108.6 . . ?
C00M C00L C00H 120.5(6) . . ?
C00M C00L H00L 119.8 . . ?
C00H C00L H00L 119.8 . . ?
C00I C00M C00L 119.9(5) . . ?
C00I C00M H00M 120.0 . . ?
C00L C00M H00M 120.0 . . ?
C00O C00N C00J 120.0(5) . . ?
C00O C00N H00N 120.0 . . ?
C00J C00N H00N 120.0 . . ?
C00N C00O C00G 120.3(6) . . ?
C00N C00O H00O 119.8 . . ?
C00G C00O H00O 119.8 . . ?
C00K C00P H00K 109.5 . . ?
C00K C00P H00P 109.5 . . ?
H00K C00P H00P 109.5 . . ?
C00K C00P H00Q 109.5 . . ?
H00K C00P H00Q 109.5 . . ?
H00P C00P H00Q 109.5 . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044



