# Electronic Supplementary Material (ESI) for ChemComm.
# 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_20230329_ys_nlg_nh3oh329_0m
_database_code_depnum_ccdc_archive 'CCDC 2255303'
loop_
_audit_author_name
_audit_author_address
'Caijin Lei Caijin Lei'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2023-03-30
_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         'C4 H3 N7 O4, H2 O'
_chemical_formula_sum            'C4 H5 N7 O5'
_chemical_formula_weight         231.15
_chemical_absolute_configuration ?
_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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   4.7059(7)
_cell_length_b                   10.5914(14)
_cell_length_c                   8.1537(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.137(5)
_cell_angle_gamma                90
_cell_volume                     405.79(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    828
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      21.985
_cell_measurement_theta_min      3.156
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.7812.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.12
_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  0.0762
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5248
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         1.923
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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         0.897
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                1267
_reflns_number_total             1776
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 473 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1776
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.033
_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)+(0.0598P)²+0.2165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
2.c Tetrahedral OH refined with riding coordinates:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.4271(11) 0.2887(4) 0.5799(7) 0.0340(13) Uani 1 1 d . . . . .
O2 O 0.7622(10) 0.3692(4) 0.4369(7) 0.0321(12) Uani 1 1 d . . . . .
O3 O 1.0087(10) 0.8044(5) 0.3059(6) 0.0293(12) Uani 1 1 d . . . . .
O4 O 0.4276(10) 1.0380(4) 0.6446(6) 0.0296(12) Uani 1 1 d . . . . .
H4 H 0.479909 1.051074 0.549183 0.044 Uiso 1 1 calc R U . . .
O5 O 0.9900(9) 1.1051(4) 0.4206(6) 0.0277(11) Uani 1 1 d G . . . .
H5A H 0.853218 1.051780 0.396731 0.042 Uiso 1 1 d G U . . .
H5B H 0.903803 1.176337 0.436350 0.042 Uiso 1 1 d G U . . .
N1 N 0.5575(12) 0.3803(5) 0.5269(7) 0.0231(13) Uani 1 1 d . . . . .
N2 N 0.2270(11) 0.6556(5) 0.6936(7) 0.0212(12) Uani 1 1 d . . . . .
H2 H 0.110479 0.696588 0.755561 0.025 Uiso 1 1 calc R U . . .
N3 N 0.4248(11) 0.7046(5) 0.5942(7) 0.0204(12) Uani 1 1 d . . . . .
N4 N 0.7747(11) 0.6456(5) 0.4084(7) 0.0210(12) Uani 1 1 d . . . . .
N5 N 0.8209(11) 0.7692(5) 0.3976(7) 0.0205(12) Uani 1 1 d . . . . .
N6 N 0.6952(11) 0.8646(5) 0.4786(7) 0.0208(12) Uani 1 1 d . . . . .
N7 N 0.3428(12) 0.9125(5) 0.6587(7) 0.0256(14) Uani 1 1 d . . . . .
C1 C 0.2523(14) 0.5320(6) 0.6746(9) 0.0208(13) Uani 1 1 d . . . . .
H1 H 0.111(17) 0.479(7) 0.723(9) 0.024(18) Uiso 1 1 d . . . . .
C2 C 0.4665(14) 0.5012(6) 0.5661(9) 0.0212(14) Uani 1 1 d . . . . .
C3 C 0.5749(12) 0.6146(7) 0.5134(8) 0.0184(14) Uani 1 1 d . . . . .
C4 C 0.4892(14) 0.8287(6) 0.5758(8) 0.0175(13) 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 1.239(7) . ?
O2 N1 1.248(8) . ?
O3 N5 1.245(6) . ?
O4 H4 0.8400 . ?
O4 N7 1.394(7) . ?
O5 H5A 0.8703 . ?
O5 H5B 0.8697 . ?
N1 C2 1.392(8) . ?
N2 H2 0.8800 . ?
N2 N3 1.370(7) . ?
N2 C1 1.325(8) . ?
N3 C3 1.376(8) . ?
N3 C4 1.359(7) . ?
N4 N5 1.331(7) . ?
N4 C3 1.347(8) . ?
N5 N6 1.360(7) . ?
N6 C4 1.341(8) . ?
N7 C4 1.330(8) . ?
C1 H1 0.97(8) . ?
C1 C2 1.415(10) . ?
C2 C3 1.383(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
N7 O4 H4 109.5 . . ?
H5A O5 H5B 104.5 . . ?
O1 N1 O2 122.9(5) . . ?
O1 N1 C2 118.4(5) . . ?
O2 N1 C2 118.6(5) . . ?
N3 N2 H2 128.1 . . ?
C1 N2 H2 128.1 . . ?
C1 N2 N3 103.7(5) . . ?
N2 N3 C3 113.8(5) . . ?
C4 N3 N2 126.5(5) . . ?
C4 N3 C3 119.6(5) . . ?
N5 N4 C3 113.8(5) . . ?
O3 N5 N4 117.3(5) . . ?
O3 N5 N6 114.3(5) . . ?
N4 N5 N6 128.4(5) . . ?
C4 N6 N5 115.1(5) . . ?
C4 N7 O4 115.8(5) . . ?
N2 C1 H1 117(4) . . ?
N2 C1 C2 111.9(6) . . ?
C2 C1 H1 130(4) . . ?
N1 C2 C1 126.5(6) . . ?
C3 C2 N1 127.1(6) . . ?
C3 C2 C1 106.3(5) . . ?
N3 C3 C2 104.2(5) . . ?
N4 C3 N3 122.0(6) . . ?
N4 C3 C2 133.8(6) . . ?
N6 C4 N3 120.8(6) . . ?
N7 C4 N3 117.7(6) . . ?
N7 C4 N6 121.5(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
O1 N1 C2 C1 6.2(10) . . . . ?
O1 N1 C2 C3 -177.0(7) . . . . ?
O2 N1 C2 C1 -175.4(7) . . . . ?
O2 N1 C2 C3 1.4(10) . . . . ?
O3 N5 N6 C4 178.9(6) . . . . ?
O4 N7 C4 N3 176.1(5) . . . . ?
O4 N7 C4 N6 -3.3(9) . . . . ?
N1 C2 C3 N3 -176.4(6) . . . . ?
N1 C2 C3 N4 4.4(11) . . . . ?
N2 N3 C3 N4 178.9(6) . . . . ?
N2 N3 C3 C2 -0.5(7) . . . . ?
N2 N3 C4 N6 177.6(6) . . . . ?
N2 N3 C4 N7 -1.7(10) . . . . ?
N2 C1 C2 N1 176.2(6) . . . . ?
N2 C1 C2 C3 -1.2(8) . . . . ?
N3 N2 C1 C2 0.8(8) . . . . ?
N4 N5 N6 C4 -3.4(9) . . . . ?
N5 N4 C3 N3 3.1(8) . . . . ?
N5 N4 C3 C2 -177.7(7) . . . . ?
N5 N6 C4 N3 2.6(9) . . . . ?
N5 N6 C4 N7 -178.0(6) . . . . ?
C1 N2 N3 C3 -0.2(7) . . . . ?
C1 N2 N3 C4 -177.3(6) . . . . ?
C1 C2 C3 N3 1.0(7) . . . . ?
C1 C2 C3 N4 -178.3(7) . . . . ?
C3 N3 C4 N6 0.7(9) . . . . ?
C3 N3 C4 N7 -178.7(6) . . . . ?
C3 N4 N5 O3 178.1(5) . . . . ?
C3 N4 N5 N6 0.5(9) . . . . ?
C4 N3 C3 N4 -3.8(9) . . . . ?
C4 N3 C3 C2 176.8(6) . . . . ?

_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_20230310_zm_nlg_lcj_ch3nh2
_database_code_depnum_ccdc_archive 'CCDC 2255305'
loop_
_audit_author_name
_audit_author_address
'Caijin Lei Caijin Lei'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2023-04-04
_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        123
_chemical_formula_moiety         'C5 H5 N7 O3, H2 O'
_chemical_formula_sum            'C5 H7 N7 O4'
_chemical_formula_weight         229.18
_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                   9.9288(3)
_cell_length_b                   13.3404(4)
_cell_length_c                   6.9157(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.535(2)
_cell_angle_gamma                90
_cell_volume                     894.18(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3666
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.81
_cell_measurement_theta_min      4.56
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    1.289
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5561
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1463 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.7384.
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    1.702
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6518
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.018
_diffrn_reflns_theta_min         4.562
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_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                1438
_reflns_number_total             1615
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.084
_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)+(0.0819P)²+0.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1467
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Free rotating group:
 O4(H4b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), N6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.21783(18) 0.38872(11) 0.4323(3) 0.0377(4) Uani 1 1 d . . . . .
N1 N 0.10459(18) 0.71539(13) 0.3641(3) 0.0278(4) Uani 1 1 d . . . . .
C1 C -0.0315(2) 0.69510(18) 0.2385(3) 0.0321(5) Uani 1 1 d . . . . .
H1A H -0.020938 0.655078 0.123863 0.048 Uiso 1 1 calc R U . . .
H1B H -0.077088 0.758615 0.192776 0.048 Uiso 1 1 calc R U . . .
H1C H -0.087652 0.658017 0.314675 0.048 Uiso 1 1 calc R U . . .
N2 N 0.15573(18) 0.54674(13) 0.3944(3) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.1887(2) 0.64277(15) 0.4375(3) 0.0236(5) Uani 1 1 d . . . . .
O2 O 0.63771(17) 0.50331(13) 0.8864(2) 0.0399(5) Uani 1 1 d . . . . .
O3 O 0.70256(19) 0.65023(15) 1.0042(3) 0.0517(5) Uani 1 1 d . . . . .
C3 C 0.3981(2) 0.58916(15) 0.6450(3) 0.0238(5) Uani 1 1 d . . . . .
N3 N 0.24922(18) 0.47680(12) 0.4795(3) 0.0271(4) Uani 1 1 d . . . . .
C4 C 0.5081(2) 0.63920(17) 0.7643(3) 0.0267(5) Uani 1 1 d . . . . .
N4 N 0.36859(18) 0.49153(13) 0.6064(3) 0.0273(4) Uani 1 1 d . . . . .
C5 C 0.4787(2) 0.74264(17) 0.7411(3) 0.0277(5) Uani 1 1 d . . . . .
H5 H 0.537596 0.794038 0.806568 0.033 Uiso 1 1 calc R U . . .
N5 N 0.31210(17) 0.66471(12) 0.5601(2) 0.0233(4) Uani 1 1 d . . . . .
N6 N 0.36015(18) 0.75919(12) 0.6183(3) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.320569 0.817205 0.581648 0.032 Uiso 1 1 calc R U . . .
N7 N 0.62316(19) 0.59484(15) 0.8919(3) 0.0330(5) Uani 1 1 d . . . . .
H4A H 0.057(5) 0.959(3) 0.301(6) 0.087(15) Uiso 1 1 d . . . . .
O4 O 0.1150(2) 0.92421(13) 0.3399(3) 0.0402(5) Uani 1 1 d G . . . .
H4B H 0.175126 0.956888 0.427732 0.060 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
O1 N3 1.241(2) . ?
N1 C1 1.465(3) . ?
N1 C2 1.307(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C2 1.340(3) . ?
N2 N3 1.357(2) . ?
C2 N5 1.362(3) . ?
O2 N7 1.231(3) . ?
O3 N7 1.227(3) . ?
C3 C4 1.388(3) . ?
C3 N4 1.349(3) . ?
C3 N5 1.368(3) . ?
N3 N4 1.327(3) . ?
C4 C5 1.412(3) . ?
C4 N7 1.413(3) . ?
C5 H5 0.9500 . ?
C5 N6 1.312(3) . ?
N5 N6 1.376(2) . ?
N6 H6 0.8800 . ?
O4 H4A 0.74(5) . ?
O4 H4B 0.8705 . ?

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 N1 C1 121.51(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 N2 N3 116.74(17) . . ?
N1 C2 N2 121.18(19) . . ?
N1 C2 N5 119.66(19) . . ?
N2 C2 N5 119.17(18) . . ?
N4 C3 C4 133.70(19) . . ?
N4 C3 N5 122.53(18) . . ?
N5 C3 C4 103.76(18) . . ?
O1 N3 N2 115.32(18) . . ?
O1 N3 N4 116.84(17) . . ?
N4 N3 N2 127.85(17) . . ?
C3 C4 C5 106.59(18) . . ?
C3 C4 N7 126.5(2) . . ?
C5 C4 N7 126.8(2) . . ?
N3 N4 C3 113.47(17) . . ?
C4 C5 H5 124.1 . . ?
N6 C5 C4 111.86(19) . . ?
N6 C5 H5 124.1 . . ?
C2 N5 C3 120.14(17) . . ?
C2 N5 N6 125.92(17) . . ?
C3 N5 N6 113.87(16) . . ?
C5 N6 N5 103.91(17) . . ?
C5 N6 H6 128.0 . . ?
N5 N6 H6 128.0 . . ?
O2 N7 C4 118.71(19) . . ?
O3 N7 O2 123.61(19) . . ?
O3 N7 C4 117.7(2) . . ?
H4A O4 H4B 107.0 . . ?

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
O1 N3 N4 C3 177.63(17) . . . . ?
N1 C2 N5 C3 177.01(17) . . . . ?
N1 C2 N5 N6 0.2(3) . . . . ?
C1 N1 C2 N2 2.6(3) . . . . ?
C1 N1 C2 N5 -177.40(18) . . . . ?
N2 C2 N5 C3 -3.0(3) . . . . ?
N2 C2 N5 N6 -179.84(17) . . . . ?
N2 N3 N4 C3 -2.6(3) . . . . ?
C2 N2 N3 O1 -177.93(17) . . . . ?
C2 N2 N3 N4 2.3(3) . . . . ?
C2 N5 N6 C5 177.29(19) . . . . ?
C3 C4 C5 N6 0.1(2) . . . . ?
C3 C4 N7 O2 7.8(3) . . . . ?
C3 C4 N7 O3 -171.4(2) . . . . ?
C3 N5 N6 C5 0.3(2) . . . . ?
N3 N2 C2 N1 -179.33(17) . . . . ?
N3 N2 C2 N5 0.7(3) . . . . ?
C4 C3 N4 N3 -179.9(2) . . . . ?
C4 C3 N5 C2 -177.40(17) . . . . ?
C4 C3 N5 N6 -0.2(2) . . . . ?
C4 C5 N6 N5 -0.2(2) . . . . ?
N4 C3 C4 C5 179.9(2) . . . . ?
N4 C3 C4 N7 -3.2(4) . . . . ?
N4 C3 N5 C2 2.7(3) . . . . ?
N4 C3 N5 N6 179.90(17) . . . . ?
C5 C4 N7 O2 -176.0(2) . . . . ?
C5 C4 N7 O3 4.8(3) . . . . ?
N5 C3 C4 C5 0.0(2) . . . . ?
N5 C3 C4 N7 176.91(19) . . . . ?
N5 C3 N4 N3 0.0(3) . . . . ?
N7 C4 C5 N6 -176.73(19) . . . . ?


_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_22019474_0m
_database_code_depnum_ccdc_archive 'CCDC 2255304'
loop_
_audit_author_name
_audit_author_address
'Caijin Lei Caijin Lei'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N7 O4, H4 N O'
_chemical_formula_sum            'C4 H6 N8 O5'
_chemical_formula_weight         246.17
_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.715(2)
_cell_length_b                   11.775(4)
_cell_length_c                   10.892(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.483(12)
_cell_angle_gamma                90
_cell_volume                     859.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3913
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.425
_cell_measurement_theta_min      2.550
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1379 before and 0.0724 after correction. The Ratio of minimum to maximum transmission is 0.7990. 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    1.902
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10060
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.550
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1558
_reflns_number_total             1977
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1676
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N8-H8B = N8-H8A = N8-H8C
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.b Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_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
O4 O 0.7988(2) 0.49624(14) 0.79520(14) 0.0240(4) Uani 1 1 d . . . . .
H4 H 0.828789 0.443173 0.844432 0.036 Uiso 1 1 calc GR . . . .
O3 O 0.5520(2) 0.80352(13) 0.56883(15) 0.0244(4) Uani 1 1 d . . . . .
O1 O 0.7139(3) 0.52293(15) 0.06885(14) 0.0305(4) Uani 1 1 d . . . . .
O2 O 0.5617(3) 0.66450(15) 0.14861(14) 0.0286(4) Uani 1 1 d . . . . .
O5 O 1.0040(3) 0.19978(18) 0.60172(17) 0.0358(5) Uani 1 1 d . . . . .
H5 H 1.013494 0.173168 0.530762 0.054 Uiso 1 1 calc GR . . . .
N2 N 0.7420(2) 0.50798(15) 0.47319(15) 0.0168(4) Uani 1 1 d . . . . .
N5 N 0.6190(2) 0.70830(15) 0.53717(16) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.8036(3) 0.40700(15) 0.42462(16) 0.0190(4) Uani 1 1 d . . . . .
N4 N 0.6901(3) 0.64179(15) 0.62709(16) 0.0192(4) Uani 1 1 d . . . . .
N8 N 0.8030(3) 0.21885(17) 0.62208(18) 0.0220(4) Uani 1 1 d D . . . .
N7 N 0.6555(3) 0.57408(16) 0.15791(16) 0.0209(4) Uani 1 1 d . . . . .
N3 N 0.8027(3) 0.45616(15) 0.67378(15) 0.0192(4) Uani 1 1 d . . . . .
N6 N 0.6047(3) 0.68836(16) 0.41679(16) 0.0195(4) Uani 1 1 d . . . . .
C4 C 0.7482(3) 0.53390(17) 0.59746(19) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.6986(3) 0.52989(19) 0.27598(18) 0.0187(5) Uani 1 1 d . . . . .
C1 C 0.7772(3) 0.42132(18) 0.30490(19) 0.0182(5) Uani 1 1 d . . . . .
H1 H 0.807268 0.365733 0.245575 0.022 Uiso 1 1 calc R . . . .
C3 C 0.6761(3) 0.58511(18) 0.38780(18) 0.0176(5) Uani 1 1 d . . . . .
H8A H 0.778(4) 0.2955(15) 0.620(2) 0.031(7) Uiso 1 1 d D . . . .
H8B H 0.720(4) 0.186(2) 0.560(2) 0.046(9) Uiso 1 1 d D . . . .
H8C H 0.786(5) 0.177(2) 0.694(2) 0.047(9) Uiso 1 1 d 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 H4 0.8400 . ?
O4 N3 1.406(2) . ?
O3 N5 1.264(2) . ?
O1 N7 1.226(2) . ?
O2 N7 1.238(3) . ?
O5 H5 0.8400 . ?
O5 N8 1.400(2) . ?
N2 N1 1.375(2) . ?
N2 C4 1.386(3) . ?
N2 C3 1.355(3) . ?
N5 N4 1.320(2) . ?
N5 N6 1.330(2) . ?
N1 C1 1.316(3) . ?
N4 C4 1.373(3) . ?
N8 H8A 0.919(17) . ?
N8 H8B 0.928(17) . ?
N8 H8C 0.937(18) . ?
N7 C2 1.401(3) . ?
N3 C4 1.275(3) . ?
N6 C3 1.351(3) . ?
C2 C1 1.411(3) . ?
C2 C3 1.397(3) . ?
C1 H1 0.9500 . ?

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
N3 O4 H4 109.5 . . ?
N8 O5 H5 109.5 . . ?
N1 N2 C4 125.06(17) . . ?
C3 N2 N1 114.13(17) . . ?
C3 N2 C4 120.79(18) . . ?
O3 N5 N4 116.26(16) . . ?
O3 N5 N6 114.84(17) . . ?
N4 N5 N6 128.89(18) . . ?
C1 N1 N2 104.18(17) . . ?
N5 N4 C4 118.00(17) . . ?
O5 N8 H8A 109.4(17) . . ?
O5 N8 H8B 111.1(19) . . ?
O5 N8 H8C 102.6(19) . . ?
H8A N8 H8B 106(2) . . ?
H8A N8 H8C 121(3) . . ?
H8B N8 H8C 107(3) . . ?
O1 N7 O2 122.90(18) . . ?
O1 N7 C2 119.05(19) . . ?
O2 N7 C2 118.04(18) . . ?
C4 N3 O4 110.56(17) . . ?
N5 N6 C3 112.57(17) . . ?
N4 C4 N2 116.19(18) . . ?
N3 C4 N2 117.97(19) . . ?
N3 C4 N4 125.8(2) . . ?
N7 C2 C1 126.50(19) . . ?
C3 C2 N7 126.9(2) . . ?
C3 C2 C1 106.61(18) . . ?
N1 C1 C2 111.29(18) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
N2 C3 C2 103.79(18) . . ?
N6 C3 N2 123.26(18) . . ?
N6 C3 C2 132.94(19) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
