# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2032618'
loop_
_audit_author_name
_audit_author_address
'Xiang Chen'
;Northwest University
China
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-23
_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         'C3 H3 N7 O'
_chemical_formula_sum            'C3 H3 N7 O'
_chemical_formula_weight         153.12
_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                   8.621(3)
_cell_length_b                   14.613(5)
_cell_length_c                   8.627(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.998(12)
_cell_angle_gamma                90
_cell_volume                     1076.2(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3324
_cell_measurement_temperature    141(2)
_cell_measurement_theta_max      26.104
_cell_measurement_theta_min      2.760
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.0195
_exptl_absorpt_correction_T_min  0.0054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0920 before and 0.0620 after correction. The Ratio of minimum to maximum transmission is 0.2769. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.890
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12102
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.453
_diffrn_reflns_theta_min         2.384
_diffrn_ambient_temperature      141.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1737
_reflns_number_total             2197
_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 V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.099
_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)+(0.0341P)²+0.3027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.482(2)
 0.518(2)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N13(H13), N6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
N12 N 0.0550(3) 0.95281(16) 0.1707(3) 0.0439(6) Uani 1 1 d . . . . .
O2 O 0.4582(2) 1.21448(13) 0.3064(2) 0.0479(5) Uani 1 1 d . . . . .
N10 N 0.4100(3) 1.06356(16) 0.3185(3) 0.0419(6) Uani 1 1 d . . . . .
O1 O 0.1821(2) 1.13080(13) -0.4498(2) 0.0437(5) Uani 1 1 d . . . . .
N9 N 0.1065(3) 1.11368(17) 0.1587(3) 0.0437(6) Uani 1 1 d . . . . .
N11 N 0.2895(3) 1.00255(18) 0.2748(3) 0.0402(5) Uani 1 1 d . . . . .
N3 N 0.1735(3) 0.97907(18) -0.4045(3) 0.0406(6) Uani 1 1 d . . . . .
N8 N 0.2128(3) 1.17306(16) 0.1950(3) 0.0422(6) Uani 1 1 d . . . . .
N5 N 0.3217(3) 0.86457(17) -0.0532(3) 0.0427(6) Uani 1 1 d . . . . .
N13 N 0.1474(3) 0.88329(17) 0.2368(3) 0.0418(6) Uani 1 1 d . . . . .
H13 H 0.116912 0.825830 0.237322 0.050 Uiso 1 1 calc R . . . .
N14 N 0.4077(3) 0.8636(2) 0.3726(3) 0.0458(6) Uani 1 1 d . . . . .
N2 N 0.3321(3) 1.02661(18) -0.0987(3) 0.0423(6) Uani 1 1 d . . . . .
N1 N 0.2927(3) 1.08742(18) -0.2037(3) 0.0424(6) Uani 1 1 d . . . . .
N7 N 0.1145(3) 0.7815(2) -0.4102(3) 0.0472(6) Uani 1 1 d . . . . .
C5 C 0.1457(3) 1.02457(19) 0.1973(3) 0.0397(6) Uani 1 1 d . . . . .
C2 C 0.2938(3) 0.9379(2) -0.1396(3) 0.0404(7) Uani 1 1 d . . . . .
C4 C 0.3669(3) 1.1482(2) 0.2762(3) 0.0409(7) Uani 1 1 d . . . . .
N4 N 0.2152(3) 0.91786(17) -0.2846(3) 0.0400(6) Uani 1 1 d . . . . .
N6 N 0.2535(3) 0.79685(17) -0.1477(3) 0.0428(6) Uani 1 1 d . . . . .
H6 H 0.252332 0.739039 -0.119291 0.051 Uiso 1 1 calc R . . . .
C1 C 0.2129(3) 1.0632(2) -0.3585(4) 0.0407(7) Uani 1 1 d . . . . .
C6 C 0.2895(3) 0.9122(2) 0.3007(3) 0.0394(6) Uani 1 1 d . . . . .
C3 C 0.1879(3) 0.82749(19) -0.2888(3) 0.0402(7) Uani 1 1 d . . . . .
H7A H 0.105(4) 0.722(3) -0.400(4) 0.050(9) Uiso 1 1 d . . . . .
H14A H 0.384(4) 0.804(3) 0.392(4) 0.063(11) Uiso 1 1 d . . . . .
H7B H 0.031(5) 0.813(2) -0.477(4) 0.069(12) Uiso 1 1 d . . . . .
H14B H 0.470(4) 0.889(2) 0.444(4) 0.054(10) 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
N12 N13 1.365(3) . ?
N12 C5 1.309(4) . ?
O2 C4 1.252(3) . ?
N10 N11 1.381(3) . ?
N10 C4 1.328(4) . ?
O1 C1 1.268(4) . ?
N9 N8 1.269(3) . ?
N9 C5 1.375(4) . ?
N11 C5 1.362(3) . ?
N11 C6 1.339(4) . ?
N3 N4 1.377(3) . ?
N3 C1 1.322(4) . ?
N8 C4 1.459(4) . ?
N5 C2 1.308(4) . ?
N5 N6 1.362(3) . ?
N13 H13 0.8800 . ?
N13 C6 1.340(4) . ?
N14 C6 1.323(4) . ?
N14 H14A 0.92(4) . ?
N14 H14B 0.85(3) . ?
N2 N1 1.281(3) . ?
N2 C2 1.372(4) . ?
N1 C1 1.458(4) . ?
N7 C3 1.328(4) . ?
N7 H7A 0.88(4) . ?
N7 H7B 0.98(4) . ?
C2 N4 1.369(4) . ?
N4 C3 1.341(4) . ?
N6 H6 0.8800 . ?
N6 C3 1.346(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
C5 N12 N13 102.9(2) . . ?
C4 N10 N11 110.9(2) . . ?
N8 N9 C5 116.3(2) . . ?
C5 N11 N10 125.4(2) . . ?
C6 N11 N10 127.5(2) . . ?
C6 N11 C5 107.1(2) . . ?
C1 N3 N4 110.5(2) . . ?
N9 N8 C4 121.8(2) . . ?
C2 N5 N6 102.9(2) . . ?
N12 N13 H13 123.7 . . ?
C6 N13 N12 112.6(2) . . ?
C6 N13 H13 123.7 . . ?
C6 N14 H14A 115(2) . . ?
C6 N14 H14B 119(2) . . ?
H14A N14 H14B 115(3) . . ?
N1 N2 C2 116.3(2) . . ?
N2 N1 C1 121.6(2) . . ?
C3 N7 H7A 117(2) . . ?
C3 N7 H7B 117(2) . . ?
H7A N7 H7B 118(3) . . ?
N12 C5 N9 126.6(3) . . ?
N12 C5 N11 112.2(3) . . ?
N11 C5 N9 121.2(3) . . ?
N5 C2 N2 127.5(3) . . ?
N5 C2 N4 112.0(3) . . ?
N4 C2 N2 120.5(3) . . ?
O2 C4 N10 121.3(3) . . ?
O2 C4 N8 114.3(2) . . ?
N10 C4 N8 124.4(3) . . ?
C2 N4 N3 126.3(2) . . ?
C3 N4 N3 126.4(2) . . ?
C3 N4 C2 107.3(3) . . ?
N5 N6 H6 123.5 . . ?
C3 N6 N5 113.1(2) . . ?
C3 N6 H6 123.5 . . ?
O1 C1 N3 121.0(3) . . ?
O1 C1 N1 114.3(3) . . ?
N3 C1 N1 124.7(3) . . ?
N11 C6 N13 105.3(2) . . ?
N14 C6 N11 126.1(3) . . ?
N14 C6 N13 128.7(3) . . ?
N7 C3 N4 125.6(3) . . ?
N7 C3 N6 129.7(3) . . ?
N4 C3 N6 104.7(3) . . ?

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
N13 H13 O2 0.88 1.77 2.638(3) 167.3 2_545 yes
N13 H13 N8 0.88 2.69 3.323(4) 129.7 2_545 yes
N6 H6 O1 0.88 1.76 2.602(3) 160.7 2_544 yes
N6 H6 N1 0.88 2.69 3.321(4) 129.8 2_544 yes
N7 H7A N1 0.88(4) 2.29(4) 3.071(4) 149(3) 2_544 yes
N14 H14A N8 0.92(4) 2.17(4) 3.001(4) 149(3) 2_545 yes
N7 H7B O1 0.98(4) 2.03(4) 2.963(4) 160(3) 3_574 yes
N14 H14B O2 0.85(3) 2.63(3) 3.069(3) 114(3) 3_676 yes
N14 H14B N10 0.85(3) 2.27(3) 3.088(4) 163(3) 3_676 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
N12 N13 C6 N11 -0.3(3) . . . . ?
N12 N13 C6 N14 -179.4(3) . . . . ?
N10 N11 C5 N12 179.8(3) . . . . ?
N10 N11 C5 N9 -1.8(4) . . . . ?
N10 N11 C6 N13 180.0(3) . . . . ?
N10 N11 C6 N14 -0.9(5) . . . . ?
N9 N8 C4 O2 -178.8(3) . . . . ?
N9 N8 C4 N10 0.2(4) . . . . ?
N11 N10 C4 O2 179.1(3) . . . . ?
N11 N10 C4 N8 0.2(4) . . . . ?
N3 N4 C3 N7 -0.4(5) . . . . ?
N3 N4 C3 N6 178.3(2) . . . . ?
N8 N9 C5 N12 -179.8(3) . . . . ?
N8 N9 C5 N11 2.0(4) . . . . ?
N5 C2 N4 N3 -177.5(2) . . . . ?
N5 C2 N4 C3 1.8(3) . . . . ?
N5 N6 C3 N7 178.7(3) . . . . ?
N5 N6 C3 N4 0.0(3) . . . . ?
N13 N12 C5 N9 -177.7(3) . . . . ?
N13 N12 C5 N11 0.7(3) . . . . ?
N2 N1 C1 O1 -179.7(2) . . . . ?
N2 N1 C1 N3 0.4(4) . . . . ?
N2 C2 N4 N3 3.4(4) . . . . ?
N2 C2 N4 C3 -177.3(3) . . . . ?
N1 N2 C2 N5 179.9(3) . . . . ?
N1 N2 C2 N4 -1.2(4) . . . . ?
C5 N12 N13 C6 -0.2(3) . . . . ?
C5 N9 N8 C4 -1.2(4) . . . . ?
C5 N11 C6 N13 0.7(3) . . . . ?
C5 N11 C6 N14 179.8(3) . . . . ?
C2 N5 N6 C3 1.0(3) . . . . ?
C2 N2 N1 C1 -0.5(4) . . . . ?
C2 N4 C3 N7 -179.8(3) . . . . ?
C2 N4 C3 N6 -1.1(3) . . . . ?
C4 N10 N11 C5 0.6(4) . . . . ?
C4 N10 N11 C6 -178.6(3) . . . . ?
N4 N3 C1 O1 -178.5(3) . . . . ?
N4 N3 C1 N1 1.4(4) . . . . ?
N6 N5 C2 N2 177.3(3) . . . . ?
N6 N5 C2 N4 -1.7(3) . . . . ?
C1 N3 N4 C2 -3.2(4) . . . . ?
C1 N3 N4 C3 177.5(3) . . . . ?
C6 N11 C5 N12 -0.9(3) . . . . ?
C6 N11 C5 N9 177.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.482(2)
2 0.518(2)

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2054180'
loop_
_audit_author_name
_audit_author_address
'Xiang Chen'
;Northwest University
China
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-21
_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         'C3 H2 N6 O'
_chemical_formula_sum            'C3 H2 N6 O'
_chemical_formula_weight         138.11
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.6514(15)
_cell_length_b                   5.2884(6)
_cell_length_c                   7.4471(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.903(4)
_cell_angle_gamma                90
_cell_volume                     497.61(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      38.84
_cell_measurement_theta_min      6.192
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1536 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.8800. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1552
_diffrn_reflns_point_group_measured_fraction_full 0.757
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         6.192
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.586
_reflns_Friedel_fraction_max     0.572
_reflns_number_gt                819
_reflns_number_total             827
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 301 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         827
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.065
_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)+(0.0332P)²+0.2020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0641
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.33672(12) 0.4639(3) 0.69453(19) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.281433 0.540371 0.709159 0.034 Uiso 1 1 calc GR . . . .
N1 N 0.49132(13) 0.5116(3) 0.57006(19) 0.0176(4) Uani 1 1 d . . . . .
N2 N 0.54554(14) 0.6711(3) 0.4653(2) 0.0156(4) Uani 1 1 d . . . . .
N3 N 0.35284(13) 0.8296(4) 0.5323(2) 0.0179(4) Uani 1 1 d . . . . .
N6 N 0.66363(15) 0.8564(3) 0.3130(2) 0.0218(4) Uani 1 1 d . . . . .
N4 N 0.40748(14) 0.9740(3) 0.4338(2) 0.0189(4) Uani 1 1 d . . . . .
N5 N 0.57805(15) 1.0114(3) 0.3052(2) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.50677(17) 0.8958(4) 0.3993(3) 0.0168(4) Uani 1 1 d . . . . .
C1 C 0.39768(16) 0.6005(3) 0.5976(3) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.64387(17) 0.6528(4) 0.4101(3) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.690583 0.520190 0.435322 0.025 Uiso 1 1 calc R . . . .


_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 H1 0.8200 . ?
O1 C1 1.302(3) . ?
N1 N2 1.358(2) . ?
N1 C1 1.300(3) . ?
N2 C2 1.368(3) . ?
N2 C3 1.333(3) . ?
N3 N4 1.285(3) . ?
N3 C1 1.414(2) . ?
N6 N5 1.357(3) . ?
N6 C3 1.328(3) . ?
N4 C2 1.359(3) . ?
N5 C2 1.320(3) . ?
C3 H3 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
C1 O1 H1 109.5 . . ?
C1 N1 N2 110.91(16) . . ?
N1 N2 C2 124.31(18) . . ?
C3 N2 N1 129.66(17) . . ?
C3 N2 C2 106.00(17) . . ?
N4 N3 C1 119.19(18) . . ?
C3 N6 N5 109.96(18) . . ?
N3 N4 C2 117.16(17) . . ?
C2 N5 N6 105.24(17) . . ?
N4 C2 N2 120.95(19) . . ?
N5 C2 N2 110.54(19) . . ?
N5 C2 N4 128.50(17) . . ?
O1 C1 N3 115.32(18) . . ?
N1 C1 O1 117.20(17) . . ?
N1 C1 N3 127.48(19) . . ?
N2 C3 H3 125.9 . . ?
N6 C3 N2 108.26(17) . . ?
N6 C3 H3 125.9 . . ?

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
O1 H1 N6 0.82 1.80 2.583(2) 159.7 4_465 yes
C3 H3 N3 0.93 2.37 3.240(3) 156.2 3_545 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
N1 N2 C2 N4 -1.0(3) . . . . ?
N1 N2 C2 N5 178.75(17) . . . . ?
N1 N2 C3 N6 -178.67(17) . . . . ?
N2 N1 C1 O1 179.17(16) . . . . ?
N2 N1 C1 N3 0.0(2) . . . . ?
N3 N4 C2 N2 0.8(3) . . . . ?
N3 N4 C2 N5 -178.85(19) . . . . ?
N6 N5 C2 N2 -0.3(2) . . . . ?
N6 N5 C2 N4 179.40(18) . . . . ?
N4 N3 C1 O1 -179.27(18) . . . . ?
N4 N3 C1 N1 0.0(3) . . . . ?
N5 N6 C3 N2 0.5(2) . . . . ?
C2 N2 C3 N6 -0.65(19) . . . . ?
C1 N1 N2 C2 0.5(2) . . . . ?
C1 N1 N2 C3 178.24(18) . . . . ?
C1 N3 N4 C2 -0.3(2) . . . . ?
C3 N2 C2 N4 -179.13(17) . . . . ?
C3 N2 C2 N5 0.6(2) . . . . ?
C3 N6 N5 C2 -0.1(2) . . . . ?

_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_b
_database_code_depnum_ccdc_archive 'CCDC 2054181'
loop_
_audit_author_name
_audit_author_address
'Xiang Chen'
;Northwest University
China
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
_audit_creation_date             2020-11-17
_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         'C3 H N6 O, H4 N, H2 O'
_chemical_formula_sum            'C3 H7 N7 O2'
_chemical_formula_weight         173.16
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   4.0295(11)
_cell_length_b                   12.201(3)
_cell_length_c                   14.678(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.823(10)
_cell_angle_gamma                90
_cell_volume                     721.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2879
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      34.83
_cell_measurement_theta_min      3.62
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.3881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1687 before and 0.0935 after correction. The Ratio of minimum to maximum transmission is 0.5196. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4877
_diffrn_reflns_point_group_measured_fraction_full 0.757
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.850
_diffrn_reflns_theta_min         3.617
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.402
_reflns_Friedel_fraction_full    0.531
_reflns_Friedel_fraction_max     0.397
_reflns_number_gt                1984
_reflns_number_total             2185
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.083
_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)+(0.0719P)²+0.3526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1592
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O2-H2A = O2-H2B
 0.85 with sigma of 0.02
 H2A-H2B
 1.34 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.4727(6) 0.23788(18) 0.41106(16) 0.0318(5) Uani 1 1 d . . . . .
N6 N 1.2768(6) 0.38558(17) 0.70227(18) 0.0240(4) Uani 1 1 d . . . . .
N7 N 0.7060(6) 0.53450(18) 0.35930(17) 0.0224(4) Uani 1 1 d . . . . .
H7A H 0.835(11) 0.487(4) 0.341(3) 0.034 Uiso 1 1 d R . . . .
H7B H 0.612(12) 0.516(4) 0.408(3) 0.034 Uiso 1 1 d R . . . .
H7C H 0.571(12) 0.554(3) 0.313(3) 0.034 Uiso 1 1 d R . . . .
H7D H 0.814(11) 0.592(4) 0.372(3) 0.034 Uiso 1 1 d R . . . .
N2 N 0.9513(5) 0.34643(16) 0.58516(14) 0.0157(4) Uani 1 1 d . . . . .
N1 N 0.7320(5) 0.35087(16) 0.51215(15) 0.0181(4) Uani 1 1 d . . . . .
N3 N 0.8203(6) 0.15146(17) 0.51215(17) 0.0237(5) Uani 1 1 d . . . . .
N5 N 1.2928(5) 0.27500(19) 0.68917(16) 0.0234(4) Uani 1 1 d . . . . .
N4 N 1.0253(6) 0.15361(17) 0.58024(17) 0.0230(5) Uani 1 1 d . . . . .
C3 C 1.0712(6) 0.42763(18) 0.63875(18) 0.0209(4) Uani 1 1 d . . . . .
H3 H 1.018682 0.501515 0.632387 0.025 Uiso 1 1 calc R . . . .
C2 C 1.0922(6) 0.25343(18) 0.61838(17) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.6708(6) 0.2517(2) 0.47720(18) 0.0195(4) Uani 1 1 d . . . . .
O2 O 0.6494(6) 0.11927(13) 0.79810(18) 0.0289(4) Uani 1 1 d D . . . .
H2A H 0.765(12) 0.153(3) 0.836(3) 0.043 Uiso 1 1 d DR . . . .
H2B H 0.541(12) 0.158(3) 0.762(3) 0.043 Uiso 1 1 d DR . . . .


_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 C1 1.248(3) . ?
N6 N5 1.365(3) . ?
N6 C3 1.330(3) . ?
N7 H7A 0.83(5) . ?
N7 H7B 0.85(5) . ?
N7 H7C 0.89(5) . ?
N7 H7D 0.85(4) . ?
N2 N1 1.368(3) . ?
N2 C3 1.345(3) . ?
N2 C2 1.353(3) . ?
N1 C1 1.334(3) . ?
N3 N4 1.276(3) . ?
N3 C1 1.450(3) . ?
N5 C2 1.323(3) . ?
N4 C2 1.364(3) . ?
C3 H3 0.9300 . ?
O2 H2A 0.82(2) . ?
O2 H2B 0.83(2) . ?

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
C3 N6 N5 108.3(2) . . ?
H7A N7 H7B 112(5) . . ?
H7A N7 H7C 109(4) . . ?
H7A N7 H7D 109(4) . . ?
H7B N7 H7C 116(4) . . ?
H7B N7 H7D 106(4) . . ?
H7C N7 H7D 104(4) . . ?
C3 N2 N1 129.78(19) . . ?
C3 N2 C2 105.55(19) . . ?
C2 N2 N1 124.67(19) . . ?
C1 N1 N2 111.84(19) . . ?
N4 N3 C1 120.7(2) . . ?
C2 N5 N6 106.1(2) . . ?
N3 N4 C2 117.0(2) . . ?
N6 C3 N2 109.3(2) . . ?
N6 C3 H3 125.4 . . ?
N2 C3 H3 125.4 . . ?
N2 C2 N4 121.7(2) . . ?
N5 C2 N2 110.8(2) . . ?
N5 C2 N4 127.5(2) . . ?
O1 C1 N1 121.8(2) . . ?
O1 C1 N3 114.2(2) . . ?
N1 C1 N3 124.0(2) . . ?
H2A O2 H2B 115(4) . . ?

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
N7 H7A O2 0.83(5) 1.93(5) 2.761(3) 178(5) 4_554 yes
N7 H7B N1 0.85(5) 2.57(4) 3.170(3) 129(4) . yes
N7 H7B N3 0.85(5) 2.57(5) 3.116(4) 124(4) 3_455 yes
N7 H7C N6 0.89(5) 2.11(5) 3.000(3) 175(4) 2_464 yes
N7 H7D O1 0.85(4) 1.97(4) 2.800(3) 168(5) 3 yes
O2 H2A O1 0.82(2) 1.91(2) 2.710(3) 166(5) 4 yes
O2 H2B N5 0.83(2) 2.02(2) 2.843(3) 170(5) 1_455 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
N6 N5 C2 N2 0.6(3) . . . . ?
N6 N5 C2 N4 -179.5(3) . . . . ?
N2 N1 C1 O1 178.8(3) . . . . ?
N2 N1 C1 N3 -0.3(4) . . . . ?
N1 N2 C3 N6 179.5(2) . . . . ?
N1 N2 C2 N5 -180.0(2) . . . . ?
N1 N2 C2 N4 0.2(4) . . . . ?
N3 N4 C2 N2 -0.7(4) . . . . ?
N3 N4 C2 N5 179.5(3) . . . . ?
N5 N6 C3 N2 0.5(3) . . . . ?
N4 N3 C1 O1 -179.4(3) . . . . ?
N4 N3 C1 N1 -0.2(4) . . . . ?
C3 N6 N5 C2 -0.7(3) . . . . ?
C3 N2 N1 C1 -179.2(3) . . . . ?
C3 N2 C2 N5 -0.3(3) . . . . ?
C3 N2 C2 N4 179.8(3) . . . . ?
C2 N2 N1 C1 0.3(3) . . . . ?
C2 N2 C3 N6 -0.1(3) . . . . ?
C1 N3 N4 C2 0.7(4) . . . . ?

_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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2032619'
loop_
_audit_author_name
_audit_author_address
'Xiang Chen'
;Northwest University
China
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
_audit_creation_date             2020-06-29
_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         'C3 H2 N7 O, H2 O, C H6 N3'
_chemical_formula_sum            'C4 H10 N10 O2'
_chemical_formula_weight         230.22
_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   3.7934(4)
_cell_length_b                   7.4317(7)
_cell_length_c                   8.7328(8)
_cell_angle_alpha                105.198(5)
_cell_angle_beta                 100.874(5)
_cell_angle_gamma                92.381(5)
_cell_volume                     232.24(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2196
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.419
_cell_measurement_theta_min      2.470
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1434 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.7650. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3223
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         2.470
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                1670
_reflns_number_total             1933
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.184
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.151
_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)+(0.0322P)²+0.0613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O2-H2a = O2-H2b
 0.85 with sigma of 0.02
 H2a-H2b
 1.34 with sigma of 0.04
3.a X=CH2 refined with riding coordinates:
 N10(H10a,H10b), N8(H8a,H8b), N9(H9a,H9b), N1(H1a,H1b)
;
_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
O1 O 0.9332(7) 0.5659(4) 0.7724(3) 0.0306(8) Uani 1 1 d . . . . .
O2 O -0.2951(8) -0.2913(4) 0.0759(3) 0.0341(8) Uani 1 1 d D . . . .
H2A H -0.214(14) -0.324(7) -0.009(4) 0.051 Uiso 1 1 d DR . . . .
H2B H -0.261(15) -0.379(6) 0.120(6) 0.051 Uiso 1 1 d DR . . . .
N7 N 0.2848(8) 0.3385(4) 0.4379(3) 0.0211(7) Uani 1 1 d . . . . .
N6 N 0.5567(8) 0.3492(4) 0.5705(4) 0.0222(8) Uani 1 1 d . . . . .
N10 N 1.2817(10) 0.9792(5) 0.9231(4) 0.0303(9) Uani 1 1 d . . . . .
H10A H 1.435377 1.009282 1.013864 0.036 Uiso 1 1 calc R . . . .
H10B H 1.199296 0.864075 0.878230 0.036 Uiso 1 1 calc R . . . .
N8 N 0.9352(9) 1.0615(5) 0.7118(4) 0.0287(9) Uani 1 1 d . . . . .
H8A H 0.862556 1.145277 0.664521 0.034 Uiso 1 1 calc R . . . .
H8B H 0.854737 0.945873 0.668086 0.034 Uiso 1 1 calc R . . . .
N3 N -0.0929(9) 0.4340(5) 0.2559(4) 0.0271(8) Uani 1 1 d . . . . .
N4 N 0.3082(10) 0.6654(5) 0.4705(4) 0.0278(8) Uani 1 1 d . . . . .
N9 N 1.2940(10) 1.2868(5) 0.9188(4) 0.0292(8) Uani 1 1 d . . . . .
H9A H 1.447735 1.318586 1.009482 0.035 Uiso 1 1 calc R . . . .
H9B H 1.220668 1.370586 0.871732 0.035 Uiso 1 1 calc R . . . .
N5 N 0.5578(10) 0.6853(5) 0.5965(4) 0.0269(8) Uani 1 1 d . . . . .
N2 N -0.1385(9) 0.2422(5) 0.2186(4) 0.0272(8) Uani 1 1 d . . . . .
N1 N 0.1389(12) 0.0095(5) 0.3304(5) 0.0363(9) Uani 1 1 d . . . . .
H1A H 0.299282 -0.014093 0.404477 0.044 Uiso 1 1 calc R . . . .
H1B H 0.006947 -0.080954 0.256780 0.044 Uiso 1 1 calc R . . . .
C3 C 0.6843(10) 0.5256(5) 0.6487(5) 0.0229(9) Uani 1 1 d . . . . .
C4 C 1.1716(10) 1.1108(6) 0.8523(5) 0.0248(9) Uani 1 1 d . . . . .
C1 C 0.0951(11) 0.1853(6) 0.3295(5) 0.0245(8) Uani 1 1 d . . . . .
C2 C 0.1637(11) 0.4889(6) 0.3886(5) 0.0241(9) 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 C3 1.253(5) . ?
N7 N6 1.380(4) . ?
N7 C1 1.349(5) . ?
N7 C2 1.366(5) . ?
N6 C3 1.332(5) . ?
N10 C4 1.329(5) . ?
N8 C4 1.329(5) . ?
N3 N2 1.372(5) . ?
N3 C2 1.323(6) . ?
N4 N5 1.280(5) . ?
N4 C2 1.354(5) . ?
N9 C4 1.309(6) . ?
N5 C3 1.448(5) . ?
N2 C1 1.350(5) . ?
N1 C1 1.326(5) . ?

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
C1 N7 N6 129.0(3) . . ?
C1 N7 C2 106.2(3) . . ?
C2 N7 N6 124.8(3) . . ?
C3 N6 N7 111.9(3) . . ?
C2 N3 N2 106.0(3) . . ?
N5 N4 C2 117.4(3) . . ?
N4 N5 C3 121.5(3) . . ?
C1 N2 N3 108.7(3) . . ?
O1 C3 N6 122.0(4) . . ?
O1 C3 N5 114.5(3) . . ?
N6 C3 N5 123.5(3) . . ?
N10 C4 N8 119.1(4) . . ?
N9 C4 N10 120.9(4) . . ?
N9 C4 N8 120.0(4) . . ?
N7 C1 N2 108.3(3) . . ?
N1 C1 N7 125.5(4) . . ?
N1 C1 N2 126.2(4) . . ?
N3 C2 N7 110.8(4) . . ?
N3 C2 N4 128.3(4) . . ?
N4 C2 N7 120.9(3) . . ?

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
O2 H2A O1 0.83(3) 2.06(3) 2.892(4) 172(5) 1_444 yes
O2 H2B N3 0.84(3) 2.10(3) 2.930(4) 170(6) 1_545 yes
N10 H10A O2 0.86 2.64 3.044(5) 110.4 1_766 yes
N10 H10A N2 0.86 2.42 3.189(5) 149.1 1_766 yes
N10 H10B O1 0.86 2.27 3.131(5) 174.1 . yes
N8 H8A N6 0.86 2.18 3.020(4) 165.3 1_565 yes
N8 H8B N5 0.86 2.08 2.920(4) 165.2 . yes
N9 H9A N3 0.86 2.43 3.285(5) 174.1 1_766 yes
N9 H9A N2 0.86 2.38 3.161(5) 151.4 1_766 yes
N9 H9B O1 0.86 2.12 2.963(5) 167.4 1_565 yes
N1 H1A N4 0.86 2.59 3.151(5) 123.5 1_545 yes
N1 H1B O2 0.86 2.03 2.891(5) 177.6 . yes

_olex2_submission_special_instructions 'No special instructions were received'
