# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_gjy20240619c_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2415224'
loop_
_audit_author_name
_audit_author_address
'Gao-Yu Zhao'
;GUES
China
;
_audit_update_record             
;
2025-01-07 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_audit_creation_date             2024-06-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N2 O4, N O3'
_chemical_formula_sum            'C9 H11 N3 O7'
_chemical_formula_weight         273.21
_chemical_absolute_configuration ad
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.672(4)
_cell_length_b                   7.971(6)
_cell_length_c                   26.69(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1206.7(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1753
_cell_measurement_temperature    300
_cell_measurement_theta_max      16.892
_cell_measurement_theta_min      2.667
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0981 before and 0.0826 after correction.
The Ratio of minimum to maximum transmission is 0.7644.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1221
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.586
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_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
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1510
_reflns_number_total             2783
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.018
_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)+(0.0432P)²+0.5943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1698
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(4)
 0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3A), C6(H6), C2(H2)
3.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_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
O4 O 0.5382(7) 0.7782(4) 0.47370(15) 0.0710(11) Uani 1 1 d . . . . .
O3 O 0.3926(10) 0.9242(5) 0.41033(18) 0.0976(17) Uani 1 1 d . . . . .
N2 N 0.2769(7) 0.5101(5) 0.45471(15) 0.0579(10) Uani 1 1 d . . . . .
H2A H 0.170581 0.431959 0.447158 0.070 Uiso 1 1 calc R U . . .
H2B H 0.250648 0.547867 0.485594 0.070 Uiso 1 1 calc R U . . .
H2C H 0.420804 0.465959 0.453048 0.070 Uiso 1 1 calc R U . . .
O7 O 0.5720(7) 1.1969(5) 0.44605(19) 0.0843(13) Uani 1 1 d . . . . .
O6 O 0.7886(7) 1.4138(5) 0.44263(17) 0.0853(13) Uani 1 1 d . . . . .
N3 N 0.7756(8) 1.2590(6) 0.44561(17) 0.0668(12) Uani 1 1 d . . . . .
O5 O 0.9488(8) 1.1713(6) 0.45000(19) 0.0994(15) Uani 1 1 d . . . . .
N1 N -0.2717(10) 0.0815(8) 0.2876(2) 0.0843(15) Uani 1 1 d . . . . .
O1 O -0.4267(9) 0.1240(7) 0.2581(2) 0.117(2) Uani 1 1 d . . . . .
C8 C 0.2579(9) 0.6508(6) 0.41866(18) 0.0526(11) Uani 1 1 d . . . . .
C9 C 0.4133(9) 0.7905(6) 0.4378(2) 0.0580(12) Uani 1 1 d . . . . .
C1 C -0.1127(10) 0.2164(7) 0.3057(2) 0.0611(13) Uani 1 1 d . . . . .
C4 C 0.1736(8) 0.4644(6) 0.34333(17) 0.0556(12) Uani 1 1 d . . . . .
C5 C -0.0320(9) 0.5052(7) 0.3173(2) 0.0631(14) Uani 1 1 d . . . . .
H5 H -0.073088 0.617310 0.313159 0.076 Uiso 1 1 calc R U . . .
O2 O -0.2354(13) -0.0608(7) 0.3012(2) 0.134(2) Uani 1 1 d . . . . .
C3 C 0.2307(10) 0.2977(6) 0.3487(2) 0.0650(13) Uani 1 1 d . . . . .
H3A H 0.369881 0.268862 0.364954 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3285(9) 0.5988(7) 0.3655(2) 0.0650(14) Uani 1 1 d . . . . .
H7A H 0.323226 0.696820 0.344001 0.078 Uiso 1 1 calc R U . . .
H7B H 0.489989 0.558697 0.366048 0.078 Uiso 1 1 calc R U . . .
C6 C -0.1746(9) 0.3823(8) 0.29785(19) 0.0656(14) Uani 1 1 d . . . . .
H6 H -0.309408 0.409771 0.279811 0.079 Uiso 1 1 calc R U . . .
C2 C 0.0871(11) 0.1723(7) 0.3305(2) 0.0694(15) Uani 1 1 d . . . . .
H2 H 0.126001 0.059986 0.335126 0.083 Uiso 1 1 calc R U . . .
H3 H 0.487(12) 1.017(8) 0.422(3) 0.10(2) Uiso 1 1 d . . . . .
H8 H 0.079(10) 0.691(6) 0.4178(18) 0.062(14) Uiso 1 1 d . . . . .


_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
O4 C9 1.196(6) . ?
O3 C9 1.299(6) . ?
O3 H3 0.96(7) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C8 1.481(6) . ?
O7 N3 1.256(6) . ?
O6 N3 1.238(6) . ?
N3 O5 1.212(6) . ?
N1 O1 1.228(7) . ?
N1 C1 1.484(7) . ?
N1 O2 1.208(8) . ?
C8 C9 1.510(7) . ?
C8 C7 1.531(7) . ?
C8 H8 1.06(5) . ?
C1 C6 1.384(8) . ?
C1 C2 1.359(8) . ?
C4 C5 1.395(7) . ?
C4 C3 1.375(7) . ?
C4 C7 1.507(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(7) . ?
C3 H3A 0.9300 . ?
C3 C2 1.378(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6 0.9300 . ?
C2 H2 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
C9 O3 H3 114(4) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
O6 N3 O7 116.6(5) . . ?
O5 N3 O7 121.1(5) . . ?
O5 N3 O6 122.2(5) . . ?
O1 N1 C1 116.3(6) . . ?
O2 N1 O1 124.9(6) . . ?
O2 N1 C1 118.7(6) . . ?
N2 C8 C9 107.3(4) . . ?
N2 C8 C7 112.2(4) . . ?
N2 C8 H8 108(3) . . ?
C9 C8 C7 111.1(4) . . ?
C9 C8 H8 110(3) . . ?
C7 C8 H8 108(3) . . ?
O4 C9 O3 125.0(5) . . ?
O4 C9 C8 123.8(5) . . ?
O3 C9 C8 111.2(5) . . ?
C6 C1 N1 119.3(5) . . ?
C2 C1 N1 118.5(5) . . ?
C2 C1 C6 122.2(5) . . ?
C5 C4 C7 121.1(5) . . ?
C3 C4 C5 118.3(5) . . ?
C3 C4 C7 120.6(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C3 H3A 119.1 . . ?
C4 C3 C2 121.7(5) . . ?
C2 C3 H3A 119.1 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C4 C7 C8 113.8(4) . . ?
C4 C7 H7A 108.8 . . ?
C4 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.4(5) . . ?
C5 C6 H6 120.8 . . ?
C1 C2 C3 118.5(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O7 0.96(7) 1.65(7) 2.582(6) 163(6) . yes

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
N2 C8 C9 O4 4.9(7) . . . . ?
N2 C8 C9 O3 -175.0(5) . . . . ?
N2 C8 C7 C4 62.3(6) . . . . ?
N1 C1 C6 C5 176.3(5) . . . . ?
N1 C1 C2 C3 -177.9(5) . . . . ?
O1 N1 C1 C6 13.9(8) . . . . ?
O1 N1 C1 C2 -167.6(6) . . . . ?
C9 C8 C7 C4 -177.6(4) . . . . ?
C4 C5 C6 C1 1.6(8) . . . . ?
C4 C3 C2 C1 1.6(9) . . . . ?
C5 C4 C3 C2 -2.1(8) . . . . ?
C5 C4 C7 C8 87.8(6) . . . . ?
O2 N1 C1 C6 -168.9(6) . . . . ?
O2 N1 C1 C2 9.6(8) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C3 C4 C7 C8 -91.6(6) . . . . ?
C7 C8 C9 O4 -118.1(6) . . . . ?
C7 C8 C9 O3 62.1(6) . . . . ?
C7 C4 C5 C6 -179.0(5) . . . . ?
C7 C4 C3 C2 177.3(5) . . . . ?
C6 C1 C2 C3 0.5(9) . . . . ?
C2 C1 C6 C5 -2.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(4)
2 0(4)

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2439970'
loop_
_audit_author_name
_audit_author_address
'Gao-Yu Zhao'
;Guizhou University of Engineering science
China
;
_audit_update_record             
;
2025-04-01 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_audit_creation_date             2024-11-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N2 O4, N O3'
_chemical_formula_sum            'C9 H11 N3 O7'
_chemical_formula_weight         273.21
_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      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                   13.9826(6)
_cell_length_b                   5.6016(3)
_cell_length_c                   15.9230(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.970(2)
_cell_angle_gamma                90
_cell_volume                     1204.84(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5648
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.2603
_exptl_absorpt_correction_T_min  0.1756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1193 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.6746.
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    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12622
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.548
_diffrn_reflns_theta_min         2.648
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_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                2082
_reflns_number_total             2478
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.041
_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)+(0.0422P)²+0.6585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O1 O 0.52257(9) 0.0563(2) 0.64376(9) 0.0325(3) Uani 1 1 d . . . . .
N1 N 0.45177(10) 0.1700(3) 0.65601(9) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.40316(11) 0.3421(3) 0.58852(10) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.41904(10) 0.1453(2) 0.71962(8) 0.0310(3) Uani 1 1 d . . . . .
N2 N 0.08084(9) 0.7773(2) 0.39030(8) 0.0133(3) Uani 1 1 d . . . . .
H2A H 0.020219 0.729666 0.358095 0.016 Uiso 1 1 calc R U . . .
H2B H 0.078416 0.934286 0.404319 0.016 Uiso 1 1 calc R U . . .
H2C H 0.098513 0.688736 0.439813 0.016 Uiso 1 1 calc R U . . .
C2 C 0.35625(11) 0.5377(3) 0.61251(10) 0.0192(4) Uani 1 1 d . . . . .
H2 H 0.355229 0.561635 0.671333 0.023 Uiso 1 1 calc R U . . .
O3 O 0.17116(9) 0.8318(2) 0.20002(7) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.149827 0.910680 0.154123 0.038 Uiso 1 1 calc R U . . .
C3 C 0.31039(11) 0.6990(3) 0.54793(10) 0.0186(3) Uani 1 1 d . . . . .
H3A H 0.279112 0.837135 0.563074 0.022 Uiso 1 1 calc R U . . .
O4 O 0.05459(8) 1.0337(2) 0.24496(7) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.30999(11) 0.6598(3) 0.46150(10) 0.0153(3) Uani 1 1 d . . . . .
C5 C 0.35864(11) 0.4603(3) 0.44024(10) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.358840 0.433347 0.381378 0.021 Uiso 1 1 calc R U . . .
C6 C 0.40674(11) 0.3005(3) 0.50378(10) 0.0187(3) Uani 1 1 d . . . . .
H6 H 0.441113 0.166548 0.489495 0.022 Uiso 1 1 calc R U . . .
C7 C 0.25825(11) 0.8289(3) 0.39003(10) 0.0171(3) Uani 1 1 d . . . . .
H7A H 0.299891 0.849582 0.348834 0.021 Uiso 1 1 calc R U . . .
H7B H 0.251869 0.986853 0.415971 0.021 Uiso 1 1 calc R U . . .
C8 C 0.15472(10) 0.7435(3) 0.33930(9) 0.0129(3) Uani 1 1 d . . . . .
H8 H 0.157904 0.570544 0.324678 0.016 Uiso 1 1 calc R U . . .
C9 C 0.12002(11) 0.8865(3) 0.25588(9) 0.0140(3) Uani 1 1 d . . . . .
N3 N 0.10775(9) 1.2108(2) 0.01567(8) 0.0161(3) Uani 1 1 d . . . . .
O5 O 0.11158(10) 1.3828(2) 0.06481(8) 0.0268(3) Uani 1 1 d . . . . .
O6 O 0.10482(9) 1.2364(2) -0.06302(7) 0.0228(3) Uani 1 1 d . . . . .
O7 O 0.10548(8) 0.9980(2) 0.04377(7) 0.0184(3) Uani 1 1 d . . . . .


_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 N1 1.234(2) . ?
N1 C1 1.473(2) . ?
N1 O2 1.2223(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.383(2) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C8 1.4819(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(2) . ?
O3 H3 0.8400 . ?
O3 C9 1.3134(19) . ?
C3 H3A 0.9500 . ?
C3 C4 1.392(2) . ?
O4 C9 1.2103(19) . ?
C4 C5 1.395(2) . ?
C4 C7 1.513(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.541(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.519(2) . ?
N3 O5 1.2334(17) . ?
N3 O6 1.2514(16) . ?
N3 O7 1.2767(17) . ?

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
O1 N1 C1 117.40(14) . . ?
O2 N1 O1 124.05(14) . . ?
O2 N1 C1 118.54(14) . . ?
C2 C1 N1 118.71(14) . . ?
C2 C1 C6 122.90(14) . . ?
C6 C1 N1 118.40(15) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.11(15) . . ?
C3 C2 H2 120.9 . . ?
C9 O3 H3 109.5 . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 C2 120.69(15) . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C5 119.25(14) . . ?
C3 C4 C7 121.58(15) . . ?
C5 C4 C7 119.17(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.98(15) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.04(15) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C4 C7 H7A 108.8 . . ?
C4 C7 H7B 108.8 . . ?
C4 C7 C8 113.69(13) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N2 C8 C7 111.50(12) . . ?
N2 C8 H8 109.3 . . ?
N2 C8 C9 107.54(12) . . ?
C7 C8 H8 109.3 . . ?
C9 C8 C7 109.83(12) . . ?
C9 C8 H8 109.3 . . ?
O3 C9 C8 111.24(13) . . ?
O4 C9 O3 125.82(14) . . ?
O4 C9 C8 122.93(14) . . ?
O5 N3 O6 122.04(14) . . ?
O5 N3 O7 120.54(13) . . ?
O6 N3 O7 117.41(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
