# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_20230719_ys_nlg_dyq_5c_0m
_database_code_depnum_ccdc_archive 'CCDC 2289562'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2023-11-07 downloaded from the CCDC.
;
_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H9 N12 O2, N O3, H2 O'
_chemical_formula_sum            'C7 H11 N13 O6'
_chemical_formula_weight         373.29
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1369(4)
_cell_length_b                   8.9590(5)
_cell_length_c                   12.3118(8)
_cell_angle_alpha                99.449(2)
_cell_angle_beta                 101.389(2)
_cell_angle_gamma                110.266(2)
_cell_volume                     700.40(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2239
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      26.689
_cell_measurement_theta_min      2.666
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0673 after correction.
The Ratio of minimum to maximum transmission is 0.9473.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15036
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.581
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_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                2415
_reflns_number_total             3223
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.045
_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)+(0.0558P)²+0.3890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Rotating group:
 N11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), N2(H2), N9(H9)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N12(H12A,H12B)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.1735(3) -0.0765(2) 0.53070(17) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.3344(3) 0.0829(2) 0.56477(16) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.3698(3) 0.1206(2) 0.46051(16) 0.0212(4) Uani 1 1 d . . . . .
C4 C 0.6550(3) 0.4054(2) 0.50461(17) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.687868 0.436076 0.585806 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6470(3) 0.4007(2) 0.33324(16) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.7015(3) 0.4539(2) 0.23414(16) 0.0236(4) Uani 1 1 d . . . . .
C7 C 0.7266(3) 0.4524(2) 0.05909(17) 0.0261(4) Uani 1 1 d . . . . .
N1 N 0.0804(3) -0.1741(2) 0.59082(15) 0.0272(4) Uani 1 1 d . . . . .
H1A H -0.016796 -0.272110 0.555522 0.033 Uiso 1 1 calc R U . . .
H1B H 0.115801 -0.140944 0.666009 0.033 Uiso 1 1 calc R U . . .
N2 N 0.1278(3) -0.1186(2) 0.41627(14) 0.0255(4) Uani 1 1 d . . . . .
H2 H 0.031553 -0.213227 0.373666 0.031 Uiso 1 1 calc R U . . .
N3 N 0.2452(3) -0.0002(2) 0.37149(14) 0.0247(4) Uani 1 1 d . . . . .
N4 N 0.4373(3) 0.1654(2) 0.67854(14) 0.0287(4) Uani 1 1 d . . . . .
N5 N 0.5084(3) 0.2603(2) 0.43701(13) 0.0221(4) Uani 1 1 d . . . . .
N6 N 0.5025(3) 0.2568(2) 0.32460(14) 0.0250(4) Uani 1 1 d . . . . .
N7 N 0.7455(3) 0.4978(2) 0.44201(14) 0.0266(4) Uani 1 1 d . . . . .
N8 N 0.8181(3) 0.6044(2) 0.23869(14) 0.0275(4) Uani 1 1 d . . . . .
N9 N 0.8332(3) 0.6028(2) 0.12847(14) 0.0282(4) Uani 1 1 d . . . . .
H9 H 0.903582 0.689367 0.106895 0.034 Uiso 1 1 calc R U . . .
N10 N 0.6407(3) 0.3552(2) 0.12439(14) 0.0245(4) Uani 1 1 d . . . . .
N11 N 0.5285(3) 0.1857(2) 0.07773(15) 0.0305(4) Uani 1 1 d . . . . .
H11A H 0.595924 0.130694 0.109963 0.037 Uiso 1 1 d R U . . .
H11B H 0.404124 0.155244 0.090281 0.037 Uiso 1 1 d R U . . .
N12 N 0.7054(3) 0.4024(2) -0.05057(15) 0.0367(5) Uani 1 1 d . . . . .
H12A H 0.766421 0.472427 -0.087600 0.044 Uiso 1 1 calc R U . . .
H12B H 0.630090 0.298804 -0.087112 0.044 Uiso 1 1 calc R U . . .
O1 O 0.3748(3) 0.10203(19) 0.75363(13) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.5872(3) 0.2971(2) 0.70224(14) 0.0538(6) Uani 1 1 d . . . . .
N13 N 0.0628(3) 0.2607(2) 0.16536(17) 0.0337(4) Uani 1 1 d . . . . .
O3 O 0.0789(3) 0.3850(2) 0.2345(2) 0.0720(7) Uani 1 1 d . . . . .
O4 O 0.1782(3) 0.2733(3) 0.10056(17) 0.0577(6) Uani 1 1 d . . . . .
O5 O -0.0683(3) 0.1251(2) 0.16249(15) 0.0417(4) Uani 1 1 d . . . . .
O6 O 0.1237(3) -0.10908(19) 0.12678(13) 0.0381(4) Uani 1 1 d G . . . .
H6A H 0.184121 -0.058048 0.198635 0.057 Uiso 1 1 d G U . . .
H6B H 0.052363 -0.054094 0.102112 0.057 Uiso 1 1 d G 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
C1 C2 1.418(3) . ?
C1 N1 1.326(3) . ?
C1 N2 1.339(3) . ?
C2 C3 1.427(3) . ?
C2 N4 1.388(2) . ?
C3 N3 1.312(2) . ?
C3 N5 1.415(2) . ?
C4 H4 0.9500 . ?
C4 N5 1.355(3) . ?
C4 N7 1.316(3) . ?
C5 C6 1.455(3) . ?
C5 N6 1.315(2) . ?
C5 N7 1.366(2) . ?
C6 N8 1.301(3) . ?
C6 N10 1.381(2) . ?
C7 N9 1.334(3) . ?
C7 N10 1.354(3) . ?
C7 N12 1.312(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2 0.8800 . ?
N2 N3 1.374(2) . ?
N4 O1 1.239(2) . ?
N4 O2 1.229(2) . ?
N5 N6 1.371(2) . ?
N8 N9 1.380(2) . ?
N9 H9 0.8800 . ?
N10 N11 1.403(2) . ?
N11 H11A 0.8864 . ?
N11 H11B 0.8865 . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N13 O3 1.240(3) . ?
N13 O4 1.246(3) . ?
N13 O5 1.240(2) . ?
O6 H6A 0.8704 . ?
O6 H6B 0.8696 . ?

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
N1 C1 C2 131.70(18) . . ?
N1 C1 N2 123.34(18) . . ?
N2 C1 C2 104.95(17) . . ?
C1 C2 C3 104.97(16) . . ?
N4 C2 C1 123.01(18) . . ?
N4 C2 C3 131.74(18) . . ?
N3 C3 C2 111.18(17) . . ?
N3 C3 N5 116.33(17) . . ?
N5 C3 C2 132.48(17) . . ?
N5 C4 H4 124.8 . . ?
N7 C4 H4 124.8 . . ?
N7 C4 N5 110.48(18) . . ?
N6 C5 C6 122.66(17) . . ?
N6 C5 N7 115.67(17) . . ?
N7 C5 C6 121.67(18) . . ?
N8 C6 C5 123.36(18) . . ?
N8 C6 N10 110.77(17) . . ?
N10 C6 C5 125.87(18) . . ?
N9 C7 N10 106.41(17) . . ?
N12 C7 N9 128.7(2) . . ?
N12 C7 N10 124.91(19) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2 123.1 . . ?
C1 N2 N3 113.78(16) . . ?
N3 N2 H2 123.1 . . ?
C3 N3 N2 105.12(16) . . ?
O1 N4 C2 118.24(17) . . ?
O2 N4 C2 119.81(18) . . ?
O2 N4 O1 121.95(17) . . ?
C4 N5 C3 133.09(17) . . ?
C4 N5 N6 109.30(16) . . ?
N6 N5 C3 117.61(15) . . ?
C5 N6 N5 102.01(15) . . ?
C4 N7 C5 102.53(17) . . ?
C6 N8 N9 105.20(16) . . ?
C7 N9 N8 110.82(17) . . ?
C7 N9 H9 124.6 . . ?
N8 N9 H9 124.6 . . ?
C6 N10 N11 132.55(17) . . ?
C7 N10 C6 106.80(16) . . ?
C7 N10 N11 120.47(16) . . ?
N10 N11 H11A 109.8 . . ?
N10 N11 H11B 110.3 . . ?
H11A N11 H11B 108.7 . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
O3 N13 O4 119.9(2) . . ?
O3 N13 O5 119.0(2) . . ?
O5 N13 O4 121.0(2) . . ?
H6A O6 H6B 104.5 . . ?

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
C1 C2 C3 N3 0.3(2) . . . . ?
C1 C2 C3 N5 179.6(2) . . . . ?
C1 C2 N4 O1 -5.6(3) . . . . ?
C1 C2 N4 O2 173.8(2) . . . . ?
C1 N2 N3 C3 0.2(2) . . . . ?
C2 C1 N2 N3 0.0(2) . . . . ?
C2 C3 N3 N2 -0.3(2) . . . . ?
C2 C3 N5 C4 0.2(4) . . . . ?
C2 C3 N5 N6 180.0(2) . . . . ?
C3 C2 N4 O1 -178.6(2) . . . . ?
C3 C2 N4 O2 0.8(4) . . . . ?
C3 N5 N6 C5 -179.74(17) . . . . ?
C4 N5 N6 C5 0.1(2) . . . . ?
C5 C6 N8 N9 179.48(18) . . . . ?
C5 C6 N10 C7 -179.34(19) . . . . ?
C5 C6 N10 N11 -4.3(3) . . . . ?
C6 C5 N6 N5 179.04(18) . . . . ?
C6 C5 N7 C4 -178.93(19) . . . . ?
C6 N8 N9 C7 -0.1(2) . . . . ?
N1 C1 C2 C3 178.7(2) . . . . ?
N1 C1 C2 N4 4.1(4) . . . . ?
N1 C1 N2 N3 -178.98(18) . . . . ?
N2 C1 C2 C3 -0.2(2) . . . . ?
N2 C1 C2 N4 -174.73(19) . . . . ?
N3 C3 N5 C4 179.5(2) . . . . ?
N3 C3 N5 N6 -0.7(3) . . . . ?
N4 C2 C3 N3 174.2(2) . . . . ?
N4 C2 C3 N5 -6.5(4) . . . . ?
N5 C3 N3 N2 -179.75(16) . . . . ?
N5 C4 N7 C5 -0.4(2) . . . . ?
N6 C5 C6 N8 168.3(2) . . . . ?
N6 C5 C6 N10 -12.3(3) . . . . ?
N6 C5 N7 C4 0.5(2) . . . . ?
N7 C4 N5 C3 180.00(19) . . . . ?
N7 C4 N5 N6 0.2(2) . . . . ?
N7 C5 C6 N8 -12.4(3) . . . . ?
N7 C5 C6 N10 167.04(19) . . . . ?
N7 C5 N6 N5 -0.4(2) . . . . ?
N8 C6 N10 C7 0.1(2) . . . . ?
N8 C6 N10 N11 175.2(2) . . . . ?
N9 C7 N10 C6 -0.2(2) . . . . ?
N9 C7 N10 N11 -175.96(18) . . . . ?
N10 C6 N8 N9 0.0(2) . . . . ?
N10 C7 N9 N8 0.2(2) . . . . ?
N12 C7 N9 N8 -179.4(2) . . . . ?
N12 C7 N10 C6 179.5(2) . . . . ?
N12 C7 N10 N11 3.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_230517lu_dyq_yq_no2_0m
_database_code_depnum_ccdc_archive 'CCDC 2289566'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang '
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2023-11-07 downloaded from the CCDC.
;
_audit_creation_date             2023-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N11 O2'
_chemical_formula_sum            'C7 H7 N11 O2'
_chemical_formula_weight         277.24
_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 0.0181 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'

_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                   5.7986(5)
_cell_length_b                   13.7372(14)
_cell_length_c                   14.8998(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.940(5)
_cell_angle_gamma                90
_cell_volume                     1165.30(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    934
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      65.067
_cell_measurement_theta_min      6.050
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    1.080
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1036 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.7322.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7464
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.731
_diffrn_reflns_theta_min         4.415
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_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                1378
_reflns_number_total             2129
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      0.956
_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)+(0.0717P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N11-H11A = N9-H9A = N9-H9B
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), N2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.9014(5) 0.2546(2) 0.6941(2) 0.0361(6) Uani 1 1 d . . . . .
H1 H 0.930749 0.252158 0.759024 0.043 Uiso 1 1 calc R U . . .
C2 C 0.7175(4) 0.3004(2) 0.63789(19) 0.0335(6) Uani 1 1 d . . . . .
C3 C 0.7524(4) 0.2835(2) 0.54852(19) 0.0340(6) Uani 1 1 d . . . . .
C4 C 0.3858(4) 0.3077(2) 0.4325(2) 0.0383(7) Uani 1 1 d . . . . .
H4 H 0.276149 0.280636 0.465476 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5471(4) 0.3725(2) 0.33313(18) 0.0311(6) Uani 1 1 d . . . . .
C6 C 0.5645(4) 0.4144(2) 0.24521(18) 0.0309(6) Uani 1 1 d . . . . .
C7 C 0.6868(5) 0.4885(2) 0.13457(19) 0.0379(7) Uani 1 1 d . . . . .
N1 N 0.5378(4) 0.35391(19) 0.66970(17) 0.0413(6) Uani 1 1 d . . . . .
N2 N 1.0289(4) 0.21457(18) 0.63894(15) 0.0373(6) Uani 1 1 d . . . . .
H2 H 1.157380 0.180773 0.658748 0.045 Uiso 1 1 calc R U . . .
N3 N 0.9428(4) 0.23060(19) 0.54921(16) 0.0372(6) Uani 1 1 d . . . . .
N4 N 0.6189(4) 0.31422(18) 0.46447(15) 0.0345(6) Uani 1 1 d . . . . .
N5 N 0.7258(3) 0.35632(18) 0.39951(15) 0.0337(5) Uani 1 1 d . . . . .
N6 N 0.3310(3) 0.34369(19) 0.34971(16) 0.0378(6) Uani 1 1 d . . . . .
N7 N 0.4060(4) 0.40456(19) 0.17271(15) 0.0375(6) Uani 1 1 d . . . . .
N8 N 0.4774(4) 0.4510(2) 0.09991(16) 0.0443(6) Uani 1 1 d . . . . .
N9 N 0.8209(5) 0.5425(3) 0.0889(2) 0.0553(8) Uani 1 1 d D . . . .
N10 N 0.7496(4) 0.46625(17) 0.22430(15) 0.0315(5) Uani 1 1 d . . . . .
N11 N 0.9539(4) 0.5027(2) 0.28091(17) 0.0361(6) Uani 1 1 d D . . . .
O1 O 0.5376(4) 0.35341(19) 0.75156(16) 0.0592(7) Uani 1 1 d . . . . .
O2 O 0.3929(4) 0.39715(17) 0.61276(15) 0.0520(6) Uani 1 1 d . . . . .
H9A H 0.966(4) 0.556(2) 0.119(2) 0.046(9) Uiso 1 1 d D . . . .
H9B H 0.768(6) 0.542(3) 0.0296(13) 0.054(10) Uiso 1 1 d D . . . .
H11A H 0.910(6) 0.534(3) 0.328(2) 0.061(11) Uiso 1 1 d D . . . .
H11B H 1.027(7) 0.453(3) 0.304(3) 0.066(12) 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
C1 H1 0.9500 . ?
C1 C2 1.377(4) . ?
C1 N2 1.325(4) . ?
C2 C3 1.404(4) . ?
C2 N1 1.427(4) . ?
C3 N3 1.321(3) . ?
C3 N4 1.406(4) . ?
C4 H4 0.9500 . ?
C4 N4 1.348(3) . ?
C4 N6 1.311(4) . ?
C5 C6 1.452(4) . ?
C5 N5 1.308(3) . ?
C5 N6 1.380(3) . ?
C6 N7 1.286(3) . ?
C6 N10 1.373(3) . ?
C7 N8 1.330(4) . ?
C7 N9 1.348(4) . ?
C7 N10 1.352(4) . ?
N1 O1 1.220(3) . ?
N1 O2 1.228(3) . ?
N2 H2 0.8800 . ?
N2 N3 1.353(3) . ?
N4 N5 1.372(3) . ?
N7 N8 1.388(3) . ?
N9 H9A 0.892(18) . ?
N9 H9B 0.879(18) . ?
N10 N11 1.409(3) . ?
N11 H11A 0.894(19) . ?
N11 H11B 0.84(4) . ?

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 C1 H1 127.1 . . ?
N2 C1 H1 127.1 . . ?
N2 C1 C2 105.7(2) . . ?
C1 C2 C3 105.5(2) . . ?
C1 C2 N1 124.3(3) . . ?
C3 C2 N1 130.2(3) . . ?
C2 C3 N4 129.9(2) . . ?
N3 C3 C2 110.8(2) . . ?
N3 C3 N4 119.3(2) . . ?
N4 C4 H4 124.6 . . ?
N6 C4 H4 124.6 . . ?
N6 C4 N4 110.8(2) . . ?
N5 C5 C6 124.6(2) . . ?
N5 C5 N6 115.6(2) . . ?
N6 C5 C6 119.7(2) . . ?
N7 C6 C5 123.7(2) . . ?
N7 C6 N10 109.2(2) . . ?
N10 C6 C5 127.0(2) . . ?
N8 C7 N9 126.0(3) . . ?
N8 C7 N10 110.6(2) . . ?
N9 C7 N10 123.4(3) . . ?
O1 N1 C2 117.9(2) . . ?
O1 N1 O2 124.3(2) . . ?
O2 N1 C2 117.8(2) . . ?
C1 N2 H2 123.2 . . ?
C1 N2 N3 113.6(2) . . ?
N3 N2 H2 123.2 . . ?
C3 N3 N2 104.4(2) . . ?
C4 N4 C3 129.8(2) . . ?
C4 N4 N5 109.6(2) . . ?
N5 N4 C3 120.6(2) . . ?
C5 N5 N4 101.87(19) . . ?
C4 N6 C5 102.1(2) . . ?
C6 N7 N8 109.7(2) . . ?
C7 N8 N7 105.1(2) . . ?
C7 N9 H9A 116(2) . . ?
C7 N9 H9B 113(2) . . ?
H9A N9 H9B 128(3) . . ?
C6 N10 N11 130.8(2) . . ?
C7 N10 C6 105.4(2) . . ?
C7 N10 N11 123.3(2) . . ?
N10 N11 H11A 108(2) . . ?
N10 N11 H11B 104(3) . . ?
H11A N11 H11B 106(4) . . ?

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
C1 C2 C3 N3 0.4(3) . . . . ?
C1 C2 C3 N4 -179.4(3) . . . . ?
C1 C2 N1 O1 -5.4(4) . . . . ?
C1 C2 N1 O2 174.9(3) . . . . ?
C1 N2 N3 C3 0.2(3) . . . . ?
C2 C1 N2 N3 0.1(3) . . . . ?
C2 C3 N3 N2 -0.4(3) . . . . ?
C2 C3 N4 C4 -49.9(5) . . . . ?
C2 C3 N4 N5 131.6(3) . . . . ?
C3 C2 N1 O1 175.8(3) . . . . ?
C3 C2 N1 O2 -3.9(5) . . . . ?
C3 N4 N5 C5 179.1(3) . . . . ?
C4 N4 N5 C5 0.3(3) . . . . ?
C5 C6 N7 N8 -178.6(3) . . . . ?
C5 C6 N10 C7 179.0(3) . . . . ?
C5 C6 N10 N11 -8.5(5) . . . . ?
C6 C5 N5 N4 -178.1(3) . . . . ?
C6 C5 N6 C4 178.0(3) . . . . ?
C6 N7 N8 C7 0.0(3) . . . . ?
N1 C2 C3 N3 179.4(3) . . . . ?
N1 C2 C3 N4 -0.4(5) . . . . ?
N2 C1 C2 C3 -0.3(3) . . . . ?
N2 C1 C2 N1 -179.3(3) . . . . ?
N3 C3 N4 C4 130.3(3) . . . . ?
N3 C3 N4 N5 -48.1(4) . . . . ?
N4 C3 N3 N2 179.5(2) . . . . ?
N4 C4 N6 C5 0.2(3) . . . . ?
N5 C5 C6 N7 159.1(3) . . . . ?
N5 C5 C6 N10 -18.2(5) . . . . ?
N5 C5 N6 C4 0.0(3) . . . . ?
N6 C4 N4 C3 -178.9(3) . . . . ?
N6 C4 N4 N5 -0.3(4) . . . . ?
N6 C5 C6 N7 -18.7(4) . . . . ?
N6 C5 C6 N10 164.0(3) . . . . ?
N6 C5 N5 N4 -0.2(3) . . . . ?
N7 C6 N10 C7 1.4(3) . . . . ?
N7 C6 N10 N11 173.9(3) . . . . ?
N8 C7 N10 C6 -1.5(3) . . . . ?
N8 C7 N10 N11 -174.6(3) . . . . ?
N9 C7 N8 N7 -178.1(3) . . . . ?
N9 C7 N10 C6 177.7(3) . . . . ?
N9 C7 N10 N11 4.5(5) . . . . ?
N10 C6 N7 N8 -0.9(3) . . . . ?
N10 C7 N8 N7 1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2289564'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2023-11-07 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            'C7 H6 N12 O4'
_chemical_formula_weight         322.24

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           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                   5.6440(8)
_cell_length_b                   11.4599(13)
_cell_length_c                   19.273(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.607(7)
_cell_angle_gamma                90
_cell_volume                     1238.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4318
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      66.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.268
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10577
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_av_R_equivalents  0.1287
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.497
_diffrn_reflns_theta_max         66.881
_diffrn_reflns_theta_full        66.881
_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             2170
_reflns_number_gt                1612
_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)+(0.0986P)²+0.7644P] 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         2170
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1892
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C1 C 0.3998(6) 0.2494(3) 0.66056(15) 0.0447(8) Uani 1 1 d . . . . .
C2 C 0.2388(6) 0.3350(2) 0.63787(15) 0.0418(8) Uani 1 1 d . . . . .
C3 C 0.0716(6) 0.2709(3) 0.59487(15) 0.0452(8) Uani 1 1 d . . . . .
C4 C 0.1030(7) 0.5133(3) 0.69372(16) 0.0537(9) Uani 1 1 d . . . . .
H4 H -0.0109 0.4784 0.7182 0.064 Uiso 1 1 calc R U . . .
C5 C 0.3279(6) 0.6320(2) 0.65224(15) 0.0442(8) Uani 1 1 d . . . . .
C6 C 0.4351(6) 0.7438(2) 0.63726(15) 0.0445(8) Uani 1 1 d . . . . .
C7 C 0.6655(7) 0.8752(3) 0.59677(15) 0.0468(8) Uani 1 1 d . . . . .
N1 N 0.6193(6) 0.2595(3) 0.70746(15) 0.0583(8) Uani 1 1 d . . . . .
N2 N 0.3372(6) 0.1449(2) 0.63371(14) 0.0516(8) Uani 1 1 d . . . . .
N3 N 0.1277(6) 0.1574(2) 0.59300(14) 0.0528(8) Uani 1 1 d . . . . .
N4 N -0.1398(6) 0.3112(3) 0.55332(14) 0.0625(9) Uani 1 1 d . . . . .
N5 N 0.2410(5) 0.4558(2) 0.65397(13) 0.0444(7) Uani 1 1 d . . . . .
N6 N 0.3905(5) 0.5316(2) 0.62612(13) 0.0480(7) Uani 1 1 d . . . . .
N7 N 0.1484(6) 0.6258(2) 0.69402(15) 0.0566(8) Uani 1 1 d . . . . .
N8 N 0.6243(5) 0.7587(2) 0.59916(12) 0.0426(7) Uani 1 1 d . . . . .
N9 N 0.5078(6) 0.9238(2) 0.63230(14) 0.0538(8) Uani 1 1 d . . . . .
H9 H 0.4979 0.9977 0.6389 0.065 Uiso 1 1 calc R U . . .
N10 N 0.3602(6) 0.8437(2) 0.65789(15) 0.0541(8) Uani 1 1 d . . . . .
N11 N 0.7444(6) 0.6780(2) 0.56181(16) 0.0587(8) Uani 1 1 d . . . . .
H11A H 0.8494 0.7015 0.5360 0.070 Uiso 1 1 calc R U . . .
H11B H 0.7134 0.6048 0.5646 0.070 Uiso 1 1 calc R U . . .
N12 N 0.8309(6) 0.9253(2) 0.56396(16) 0.0645(9) Uani 1 1 d . . . . .
H12A H 0.8449 1.0000 0.5643 0.077 Uiso 1 1 calc R U . . .
H12B H 0.9248 0.8832 0.5422 0.077 Uiso 1 1 calc R U . . .
O1 O 0.7499(6) 0.1746(3) 0.71419(17) 0.0840(9) Uani 1 1 d . . . . .
O2 O 0.6522(6) 0.3526(2) 0.73811(16) 0.0787(9) Uani 1 1 d . . . . .
O3 O -0.2630(6) 0.2379(3) 0.52032(17) 0.0990(11) Uani 1 1 d . . . . .
O4 O -0.1812(7) 0.4145(3) 0.55205(17) 0.1002(12) 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
C1 N2 1.336(4) . ?
C1 C2 1.374(4) . ?
C1 N1 1.451(5) . ?
C2 C3 1.392(4) . ?
C2 N5 1.419(4) . ?
C3 N3 1.339(4) . ?
C3 N4 1.435(5) . ?
C4 N7 1.315(4) . ?
C4 N5 1.328(4) . ?
C4 H4 0.9300 . ?
C5 N6 1.321(4) . ?
C5 N7 1.366(5) . ?
C5 C6 1.459(4) . ?
C6 N10 1.299(4) . ?
C6 N8 1.374(4) . ?
C7 N9 1.308(4) . ?
C7 N12 1.317(4) . ?
C7 N8 1.358(4) . ?
N1 O1 1.219(4) . ?
N1 O2 1.223(4) . ?
N2 N3 1.349(4) . ?
N4 O4 1.206(4) . ?
N4 O3 1.221(4) . ?
N5 N6 1.363(3) . ?
N8 N11 1.394(4) . ?
N9 N10 1.368(4) . ?
N9 H9 0.8600 . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?

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
N2 C1 C2 112.4(3) . . ?
N2 C1 N1 118.8(3) . . ?
C2 C1 N1 128.9(3) . . ?
C1 C2 C3 101.0(3) . . ?
C1 C2 N5 129.7(3) . . ?
C3 C2 N5 129.3(3) . . ?
N3 C3 C2 112.5(3) . . ?
N3 C3 N4 118.8(3) . . ?
C2 C3 N4 128.7(3) . . ?
N7 C4 N5 111.2(3) . . ?
N7 C4 H4 124.4 . . ?
N5 C4 H4 124.4 . . ?
N6 C5 N7 115.4(3) . . ?
N6 C5 C6 123.7(3) . . ?
N7 C5 C6 121.0(3) . . ?
N10 C6 N8 110.7(3) . . ?
N10 C6 C5 123.8(3) . . ?
N8 C6 C5 125.4(3) . . ?
N9 C7 N12 129.0(3) . . ?
N9 C7 N8 105.7(3) . . ?
N12 C7 N8 125.3(3) . . ?
O1 N1 O2 126.0(4) . . ?
O1 N1 C1 117.8(3) . . ?
O2 N1 C1 116.2(3) . . ?
C1 N2 N3 107.7(3) . . ?
C3 N3 N2 106.4(2) . . ?
O4 N4 O3 124.5(4) . . ?
O4 N4 C3 118.3(3) . . ?
O3 N4 C3 117.1(3) . . ?
C4 N5 N6 110.0(2) . . ?
C4 N5 C2 128.2(3) . . ?
N6 N5 C2 121.7(3) . . ?
C5 N6 N5 101.5(2) . . ?
C4 N7 C5 101.9(3) . . ?
C7 N8 C6 106.7(3) . . ?
C7 N8 N11 122.6(3) . . ?
C6 N8 N11 130.3(2) . . ?
C7 N9 N10 112.5(3) . . ?
C7 N9 H9 123.7 . . ?
N10 N9 H9 123.7 . . ?
C6 N10 N9 104.3(3) . . ?
N8 N11 H11A 120.0 . . ?
N8 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?

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
N2 C1 C2 C3 0.4(4) . . . . ?
N1 C1 C2 C3 179.9(3) . . . . ?
N2 C1 C2 N5 -179.9(3) . . . . ?
N1 C1 C2 N5 -0.3(6) . . . . ?
C1 C2 C3 N3 0.6(4) . . . . ?
N5 C2 C3 N3 -179.1(3) . . . . ?
C1 C2 C3 N4 -177.8(3) . . . . ?
N5 C2 C3 N4 2.4(6) . . . . ?
N6 C5 C6 N10 173.8(3) . . . . ?
N7 C5 C6 N10 -4.7(5) . . . . ?
N6 C5 C6 N8 -5.2(5) . . . . ?
N7 C5 C6 N8 176.3(3) . . . . ?
N2 C1 N1 O1 7.9(5) . . . . ?
C2 C1 N1 O1 -171.6(3) . . . . ?
N2 C1 N1 O2 -170.2(3) . . . . ?
C2 C1 N1 O2 10.3(5) . . . . ?
C2 C1 N2 N3 -1.3(4) . . . . ?
N1 C1 N2 N3 179.2(3) . . . . ?
C2 C3 N3 N2 -1.4(4) . . . . ?
N4 C3 N3 N2 177.2(3) . . . . ?
C1 N2 N3 C3 1.6(4) . . . . ?
N3 C3 N4 O4 -175.6(4) . . . . ?
C2 C3 N4 O4 2.8(6) . . . . ?
N3 C3 N4 O3 2.8(5) . . . . ?
C2 C3 N4 O3 -178.8(3) . . . . ?
N7 C4 N5 N6 0.7(4) . . . . ?
N7 C4 N5 C2 -176.9(3) . . . . ?
C1 C2 N5 C4 -107.9(4) . . . . ?
C3 C2 N5 C4 71.8(5) . . . . ?
C1 C2 N5 N6 74.7(4) . . . . ?
C3 C2 N5 N6 -105.6(4) . . . . ?
N7 C5 N6 N5 -0.6(4) . . . . ?
C6 C5 N6 N5 -179.2(3) . . . . ?
C4 N5 N6 C5 -0.1(3) . . . . ?
C2 N5 N6 C5 177.7(3) . . . . ?
N5 C4 N7 C5 -1.0(4) . . . . ?
N6 C5 N7 C4 1.0(4) . . . . ?
C6 C5 N7 C4 179.6(3) . . . . ?
N9 C7 N8 C6 0.4(3) . . . . ?
N12 C7 N8 C6 -178.9(3) . . . . ?
N9 C7 N8 N11 174.3(3) . . . . ?
N12 C7 N8 N11 -5.0(5) . . . . ?
N10 C6 N8 C7 0.0(4) . . . . ?
C5 C6 N8 C7 179.1(3) . . . . ?
N10 C6 N8 N11 -173.2(3) . . . . ?
C5 C6 N8 N11 5.9(5) . . . . ?
N12 C7 N9 N10 178.6(3) . . . . ?
N8 C7 N9 N10 -0.6(3) . . . . ?
N8 C6 N10 N9 -0.4(3) . . . . ?
C5 C6 N10 N9 -179.5(3) . . . . ?
C7 N9 N10 C6 0.6(4) . . . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.071



####################################################################### 
# 
# 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_cu_20230612_NLG_DYQ_CH_CF3_0m
_database_code_depnum_ccdc_archive 'CCDC 2289565'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang '
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2023-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H10 N12 O4'
_chemical_formula_weight         314.26

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           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.7084(8)
_cell_length_b                   6.2936(6)
_cell_length_c                   13.2830(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.277(7)
_cell_angle_gamma                90
_cell_volume                     644.40(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.191
_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      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4552
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.327
_diffrn_reflns_theta_max         68.056
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1251
_reflns_number_gt                761
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1734P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1251
_refine_ls_number_parameters     143
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2555
_refine_ls_wR_factor_gt          0.2139
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.956
_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
N1 N 0.1975(9) 0.250000 0.4621(5) 0.0510(16) Uani 1 2 d S T P . .
C4 C 0.1382(10) 0.250000 0.3672(5) 0.0477(18) Uani 1 2 d S T P . .
N3 N 0.0513(9) 0.250000 0.5162(5) 0.0478(15) Uani 1 2 d S T P . .
N12 N 0.2028(9) 0.250000 0.6726(5) 0.0521(17) Uani 1 2 d S T P . .
N4 N -0.0382(10) 0.250000 0.3596(5) 0.0526(16) Uani 1 2 d S T P . .
C3 C -0.0865(11) 0.250000 0.4542(6) 0.0491(18) Uani 1 2 d S T P . .
H3 H -0.203702 0.250000 0.475873 0.059 Uiso 1 2 calc R U P . .
C6 C 0.2544(11) 0.250000 0.2834(5) 0.0500(19) Uani 1 2 d S T P . .
N10 N 0.5380(11) 0.250000 0.3830(5) 0.070(2) Uani 1 2 d DS T P . .
H10A H 0.521296 0.135840 0.424210 0.104 Uiso 0.5 1 d DR U P A -1
H10B H 0.539705 0.375827 0.417126 0.104 Uiso 0.5 1 d DR U P A -1
C1 C 0.0575(11) 0.250000 0.6235(6) 0.0475(17) Uani 1 2 d S T P . .
N8 N 0.4359(10) 0.250000 0.2947(5) 0.0537(17) Uani 1 2 d DS T P . .
N2 N 0.1467(9) 0.250000 0.7695(5) 0.0562(18) Uani 1 2 d S T P . .
H2A H 0.214346 0.250000 0.823053 0.067 Uiso 1 2 calc R U P . .
N11 N -0.0870(9) 0.250000 0.6772(5) 0.0513(17) Uani 1 2 d S T P . .
C2 C -0.0224(12) 0.250000 0.7710(6) 0.0522(19) Uani 1 2 d S T P . .
H2 H -0.090451 0.250000 0.830471 0.063 Uiso 1 2 calc R U P . .
O5 O 0.5590(9) 0.250000 0.5920(4) 0.0699(18) Uani 1 2 d DS T P . .
H5A H 0.466(7) 0.250000 0.626(6) 0.105 Uiso 1 2 d DS U P . .
H5B H 0.639(9) 0.250000 0.636(6) 0.105 Uiso 1 2 d DS U P . .
C7 C 0.5021(11) 0.250000 0.2015(6) 0.052(2) Uani 1 2 d DS T P . .
N9 N 0.5404(10) 0.250000 -0.0994(5) 0.0567(18) Uani 1 2 d S T P . .
N7 N 0.6744(10) 0.250000 0.1834(5) 0.0566(17) Uani 1 2 d DS T P . .
H7A H 0.718(7) 0.250000 0.121(2) 0.085 Uiso 1 2 d DS U P . .
H7B H 0.755(6) 0.27(6) 0.231(4) 0.085 Uiso 0.5 1 d D U P B -1
N5 N 0.2153(10) 0.250000 0.1877(6) 0.0600(18) Uani 1 2 d S T P . .
O4 O 0.5612(9) 0.250000 -0.1912(4) 0.0738(19) Uani 1 2 d S T P . .
N6 N 0.3711(9) 0.250000 0.1391(5) 0.0555(18) Uani 1 2 d S T P . .
H6 H 0.381798 0.250000 0.073147 0.067 Uiso 1 2 calc R U P . .
O2 O 0.3859(9) 0.250000 -0.0669(5) 0.0723(19) Uani 1 2 d S T P . .
O3 O 0.6634(10) 0.250000 -0.0392(5) 0.078(2) Uani 1 2 d S T P . .


_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
N1 C4 1.339(10) . ?
N1 N3 1.340(9) . ?
C4 N4 1.364(11) . ?
C4 C6 1.431(10) . ?
N3 C3 1.341(10) . ?
N3 C1 1.426(9) . ?
N12 C1 1.293(11) . ?
N12 N2 1.360(9) . ?
N4 C3 1.311(11) . ?
C6 N5 1.306(10) . ?
C6 N8 1.406(11) . ?
N10 N8 1.410(9) . ?
C1 N11 1.325(11) . ?
N8 C7 1.341(10) . ?
N2 C2 1.304(11) . ?
N11 C2 1.340(10) . ?
C7 N6 1.304(11) . ?
C7 N7 1.351(12) . ?
N9 O4 1.230(9) . ?
N9 O3 1.238(10) . ?
N9 O2 1.269(10) . ?
N5 N6 1.367(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
C4 N1 N3 102.8(6) . . ?
N1 C4 N4 113.9(7) . . ?
N1 C4 C6 121.3(7) . . ?
N4 C4 C6 124.8(7) . . ?
N1 N3 C3 109.6(6) . . ?
N1 N3 C1 120.8(6) . . ?
C3 N3 C1 129.6(7) . . ?
C1 N12 N2 101.4(6) . . ?
C3 N4 C4 102.5(7) . . ?
N4 C3 N3 111.2(7) . . ?
N5 C6 N8 109.2(7) . . ?
N5 C6 C4 127.9(8) . . ?
N8 C6 C4 122.9(7) . . ?
N12 C1 N11 117.2(6) . . ?
N12 C1 N3 121.9(7) . . ?
N11 C1 N3 120.9(7) . . ?
C7 N8 C6 106.6(7) . . ?
C7 N8 N10 123.7(7) . . ?
C6 N8 N10 129.8(7) . . ?
C2 N2 N12 109.7(7) . . ?
C1 N11 C2 101.0(7) . . ?
N2 C2 N11 110.6(7) . . ?
N6 C7 N8 106.8(7) . . ?
N6 C7 N7 130.3(7) . . ?
N8 C7 N7 122.9(8) . . ?
O4 N9 O3 122.5(8) . . ?
O4 N9 O2 117.7(8) . . ?
O3 N9 O2 119.8(7) . . ?
C6 N5 N6 105.1(7) . . ?
C7 N6 N5 112.3(6) . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.092



