# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1_auto
_database_code_depnum_ccdc_archive 'CCDC 2321759'
loop_
_audit_author_name
_audit_author_address
Shenxuan
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-12-26 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N2 O3'
_chemical_formula_weight         207.21

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'

_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                   10.6496(14)
_cell_length_b                   4.9316(6)
_cell_length_c                   19.212(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.692(12)
_cell_angle_gamma                90
_cell_volume                     991.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    2755
_cell_measurement_theta_min      3.4500
_cell_measurement_theta_max      26.0580

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.988
_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      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            7026
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         29.843
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2282
_reflns_number_gt                1499
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0992P)²+0.1465P] 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_number_reflns         2282
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1900
_refine_ls_wR_factor_gt          0.1734
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O9 O 0.34934(16) 0.2261(4) 0.84017(8) 0.0836(6) Uani 1 1 d . . . . .
N13 N 0.7129(2) 0.6868(5) 0.54409(11) 0.0812(6) Uani 1 1 d . . . . .
N12 N 0.5042(2) 0.5087(4) 0.82735(10) 0.0856(7) Uani 1 1 d . . . . .
H12 H 0.5616 0.5855 0.8080 0.103 Uiso 1 1 calc R U . . .
C4 C 0.64375(19) 0.5543(4) 0.59460(9) 0.0585(5) Uani 1 1 d . . . . .
O15 O 0.6669(2) 0.8845(5) 0.51191(12) 0.1206(8) Uani 1 1 d . . . . .
C8 C 0.43409(19) 0.3183(4) 0.80278(9) 0.0593(5) Uani 1 1 d . . . . .
C1 C 0.5103(2) 0.3063(4) 0.68641(9) 0.0616(5) Uani 1 1 d . . . . .
O14 O 0.8152(2) 0.5907(5) 0.53753(13) 0.1289(9) Uani 1 1 d . . . . .
C5 C 0.5202(2) 0.6319(5) 0.59464(11) 0.0685(6) Uani 1 1 d . . . . .
H5 H 0.4817 0.7672 0.5643 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4546(2) 0.5053(5) 0.64047(12) 0.0703(6) Uani 1 1 d . . . . .
H6 H 0.3704 0.5550 0.6405 0.084 Uiso 1 1 calc R U . . .
C3 C 0.7025(2) 0.3582(5) 0.63914(12) 0.0698(6) Uani 1 1 d . . . . .
H3 H 0.7863 0.3071 0.6383 0.084 Uiso 1 1 calc R U . . .
C2 C 0.6349(2) 0.2375(5) 0.68536(11) 0.0728(6) Uani 1 1 d . . . . .
H2 H 0.6747 0.1062 0.7166 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3706(3) 0.3801(6) 0.90530(12) 0.0844(7) Uani 1 1 d . . . . .
H10A H 0.3998 0.2635 0.9457 0.101 Uiso 1 1 calc R U . . .
H10B H 0.2929 0.4713 0.9119 0.101 Uiso 1 1 calc R U . . .
C7 C 0.4351(3) 0.1676(5) 0.73566(12) 0.0875(8) Uani 1 1 d . . . . .
H7A H 0.3477 0.1439 0.7110 0.105 Uiso 1 1 calc R U . . .
H7B H 0.4710 -0.0112 0.7472 0.105 Uiso 1 1 calc R U . . .
C11 C 0.4704(3) 0.5788(5) 0.89612(12) 0.0875(8) Uani 1 1 d . . . . .
H11A H 0.4377 0.7625 0.8955 0.105 Uiso 1 1 calc R U . . .
H11B H 0.5441 0.5627 0.9340 0.105 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
O9 C8 1.333(2) . ?
O9 C10 1.445(3) . ?
N13 O15 1.209(3) . ?
N13 O14 1.216(3) . ?
N13 C4 1.475(3) . ?
N12 C8 1.237(3) . ?
N12 C11 1.473(3) . ?
N12 H12 0.8600 . ?
C4 C3 1.364(3) . ?
C4 C5 1.370(3) . ?
C8 C7 1.490(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.379(3) . ?
C1 C7 1.512(3) . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C3 C2 1.378(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C10 C11 1.480(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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 O9 C10 105.94(17) . . ?
O15 N13 O14 123.2(2) . . ?
O15 N13 C4 119.3(2) . . ?
O14 N13 C4 117.5(2) . . ?
C8 N12 C11 106.84(18) . . ?
C8 N12 H12 126.6 . . ?
C11 N12 H12 126.6 . . ?
C3 C4 C5 121.76(19) . . ?
C3 C4 N13 119.97(19) . . ?
C5 C4 N13 118.26(19) . . ?
N12 C8 O9 118.29(17) . . ?
N12 C8 C7 127.44(18) . . ?
O9 C8 C7 114.24(17) . . ?
C2 C1 C6 117.97(18) . . ?
C2 C1 C7 121.5(2) . . ?
C6 C1 C7 120.5(2) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C4 C3 C2 118.48(19) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
O9 C10 C11 104.18(16) . . ?
O9 C10 H10A 110.9 . . ?
C11 C10 H10A 110.9 . . ?
O9 C10 H10B 110.9 . . ?
C11 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C8 C7 C1 113.95(18) . . ?
C8 C7 H7A 108.8 . . ?
C1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N12 C11 C10 104.59(18) . . ?
N12 C11 H11A 110.8 . . ?
C10 C11 H11A 110.8 . . ?
N12 C11 H11B 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?

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
O15 N13 C4 C3 -169.9(2) . . . . ?
O14 N13 C4 C3 9.4(3) . . . . ?
O15 N13 C4 C5 10.8(3) . . . . ?
O14 N13 C4 C5 -169.9(2) . . . . ?
C11 N12 C8 O9 0.5(3) . . . . ?
C11 N12 C8 C7 -177.2(3) . . . . ?
C10 O9 C8 N12 -3.0(3) . . . . ?
C10 O9 C8 C7 175.1(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
N13 C4 C5 C6 178.64(19) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C7 C1 C6 C5 -179.2(2) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
N13 C4 C3 C2 -179.62(19) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C7 C1 C2 C3 178.14(19) . . . . ?
C4 C3 C2 C1 1.3(3) . . . . ?
C8 O9 C10 C11 3.9(3) . . . . ?
N12 C8 C7 C1 -14.2(4) . . . . ?
O9 C8 C7 C1 167.9(2) . . . . ?
C2 C1 C7 C8 96.3(3) . . . . ?
C6 C1 C7 C8 -84.3(3) . . . . ?
C8 N12 C11 C10 2.1(3) . . . . ?
O9 C10 C11 N12 -3.6(3) . . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.038

