# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_3_a
_database_code_depnum_ccdc_archive 'CCDC 2224685'
loop_
_audit_author_name
_audit_author_address
Ca
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-07-06 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            'C3 H2 N6 O6'
_chemical_formula_weight         218.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.5399(11)
_cell_length_b                   8.8744(11)
_cell_length_c                   10.5124(14)
_cell_angle_alpha                90
_cell_angle_beta                 116.970(5)
_cell_angle_gamma                90
_cell_volume                     793.20(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8949
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      24.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             440
_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    0.176
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.969
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1732
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.318
_diffrn_reflns_theta_max         27.939
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.594
_diffrn_reflns_point_group_measured_fraction_full 0.617
_reflns_number_total             1140
_reflns_number_gt                987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.240
_reflns_Friedel_fraction_max     0.231
_reflns_Friedel_fraction_full    0.237

_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)+(0.0382P)²+0.0584P] 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_abs_structure_details 
;
 Flack x determined using 169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1140
_refine_ls_number_parameters     136
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_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 0.6672(3) 0.5493(2) 0.6391(2) 0.0325(5) Uani 1 1 d . . . . .
C2 C 0.6314(3) 0.4714(3) 0.7355(3) 0.0430(6) Uani 1 1 d . . . . .
H2 H 0.7030 0.4388 0.8260 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2677(3) 0.5383(2) 0.4580(2) 0.0336(5) Uani 1 1 d . . . . .
H3 H 0.2081 0.4652 0.4841 0.040 Uiso 1 1 calc R U . . .
N1 N 0.8217(3) 0.5977(2) 0.6602(3) 0.0420(5) Uani 1 1 d . . . . .
N2 N 0.5409(2) 0.5799(2) 0.5206(2) 0.0343(4) Uani 1 1 d . . . . .
N3 N 0.4295(2) 0.51721(19) 0.5473(2) 0.0329(4) Uani 1 1 d . . . . .
N4 N 0.4781(2) 0.4521(2) 0.6756(2) 0.0399(5) Uani 1 1 d . . . . .
N5 N 0.2145(3) 0.6972(2) 0.4718(3) 0.0452(5) Uani 1 1 d . . . . .
N6 N 0.2322(2) 0.5129(2) 0.3035(2) 0.0360(4) Uani 1 1 d . . . . .
O1 O 0.8358(2) 0.6483(2) 0.5599(2) 0.0602(5) Uani 1 1 d . . . . .
O2 O 0.9273(2) 0.5837(3) 0.7809(2) 0.0668(6) Uani 1 1 d . . . . .
O3 O 0.3144(2) 0.79130(19) 0.5289(3) 0.0668(6) Uani 1 1 d . . . . .
O4 O 0.0757(2) 0.7136(2) 0.4275(3) 0.0737(7) Uani 1 1 d . . . . .
O5 O 0.1797(2) 0.6163(2) 0.2203(2) 0.0540(5) Uani 1 1 d . . . . .
O6 O 0.2596(2) 0.38698(19) 0.2779(2) 0.0499(5) 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 1.310(3) . ?
C1 C2 1.391(4) . ?
C1 N1 1.453(3) . ?
C2 N4 1.315(3) . ?
C3 N3 1.409(3) . ?
C3 N6 1.518(3) . ?
C3 N5 1.528(3) . ?
N1 O1 1.208(3) . ?
N1 O2 1.216(3) . ?
N2 N3 1.338(3) . ?
N3 N4 1.342(3) . ?
N5 O4 1.197(3) . ?
N5 O3 1.203(3) . ?
N6 O6 1.206(3) . ?
N6 O5 1.209(3) . ?

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 111.9(2) . . ?
N2 C1 N1 121.0(2) . . ?
C2 C1 N1 127.1(2) . . ?
N4 C2 C1 107.6(2) . . ?
N3 C3 N6 109.78(17) . . ?
N3 C3 N5 111.72(18) . . ?
N6 C3 N5 108.40(18) . . ?
O1 N1 O2 125.5(2) . . ?
O1 N1 C1 118.9(2) . . ?
O2 N1 C1 115.6(2) . . ?
C1 N2 N3 100.89(18) . . ?
N2 N3 N4 116.44(18) . . ?
N2 N3 C3 122.65(18) . . ?
N4 N3 C3 120.10(18) . . ?
C2 N4 N3 103.16(18) . . ?
O4 N5 O3 126.6(2) . . ?
O4 N5 C3 115.6(2) . . ?
O3 N5 C3 117.77(19) . . ?
O6 N6 O5 127.1(2) . . ?
O6 N6 C3 114.24(19) . . ?
O5 N6 C3 118.69(19) . . ?

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 N4 0.1(3) . . . . ?
N1 C1 C2 N4 178.89(19) . . . . ?
N2 C1 N1 O1 -10.2(3) . . . . ?
C2 C1 N1 O1 171.1(2) . . . . ?
N2 C1 N1 O2 169.4(2) . . . . ?
C2 C1 N1 O2 -9.2(3) . . . . ?
C2 C1 N2 N3 -0.7(2) . . . . ?
N1 C1 N2 N3 -179.56(18) . . . . ?
C1 N2 N3 N4 1.1(2) . . . . ?
C1 N2 N3 C3 170.86(19) . . . . ?
N6 C3 N3 N2 47.7(2) . . . . ?
N5 C3 N3 N2 -72.6(3) . . . . ?
N6 C3 N3 N4 -142.9(2) . . . . ?
N5 C3 N3 N4 96.8(2) . . . . ?
C1 C2 N4 N3 0.5(2) . . . . ?
N2 N3 N4 C2 -1.1(2) . . . . ?
C3 N3 N4 C2 -171.08(19) . . . . ?
N3 C3 N5 O4 -162.8(2) . . . . ?
N6 C3 N5 O4 76.1(3) . . . . ?
N3 C3 N5 O3 15.1(3) . . . . ?
N6 C3 N5 O3 -106.0(3) . . . . ?
N3 C3 N6 O6 62.5(2) . . . . ?
N5 C3 N6 O6 -175.24(18) . . . . ?
N3 C3 N6 O5 -118.2(2) . . . . ?
N5 C3 N6 O5 4.1(3) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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 2224691'
loop_
_audit_author_name
_audit_author_address
Cb
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-07-06 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            'C3 H2 N6 O6'
_chemical_formula_weight         218.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0555(7)
_cell_length_b                   12.4013(14)
_cell_length_c                   9.0110(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.052(3)
_cell_angle_gamma                90
_cell_volume                     771.06(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5628
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      24.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.965
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11609
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.836
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_full        25.091
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1363
_reflns_number_gt                1097
_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)+(0.0492P)²+0.3883P] 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         1363
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.7080(3) 0.52862(16) 0.2242(2) 0.0330(5) Uani 1 1 d . . . A 1
H1 H 0.6801 0.4889 0.1281 0.040 Uiso 1 1 calc R U . A 1
C2 C 0.5231(3) 0.67310(15) 0.3327(2) 0.0298(5) Uani 1 1 d . . . A 1
H2 H 0.5881 0.6797 0.4333 0.036 Uiso 1 1 calc R U . A 1
C3 C 0.3691(3) 0.72983(15) 0.2573(2) 0.0283(4) Uani 1 1 d . . . A 1
N1 N 0.7361(3) 0.44981(15) 0.3544(2) 0.0429(5) Uani 1 1 d . . . A 1
N2 N 0.9076(2) 0.58113(16) 0.2446(2) 0.0407(5) Uani 1 1 d . . . A 1
N3 N 0.5589(2) 0.60474(13) 0.22562(16) 0.0293(4) Uani 1 1 d . . . A 1
N4 N 0.4294(2) 0.62076(15) 0.08982(17) 0.0356(4) Uani 1 1 d . . . A 1
N5 N 0.3157(2) 0.69785(14) 0.11151(18) 0.0359(4) Uani 1 1 d . . . A 1
N6 N 0.2676(2) 0.81490(14) 0.3159(2) 0.0356(4) Uani 1 1 d . . . A 1
O1 O 0.7930(3) 0.36202(15) 0.3286(3) 0.0841(7) Uani 1 1 d . . . A 1
O2 O 0.7045(3) 0.47993(15) 0.4718(2) 0.0783(7) Uani 1 1 d . . . A 1
O3 O 1.0275(3) 0.52850(16) 0.1999(3) 0.0736(6) Uani 1 1 d . . . A 1
O4 O 0.9300(2) 0.66755(15) 0.3042(2) 0.0621(5) Uani 1 1 d . . . A 1
O5 O 0.3097(2) 0.83003(14) 0.45193(19) 0.0554(5) Uani 1 1 d . . . A 1
O6 O 0.1486(2) 0.86619(13) 0.22651(19) 0.0509(5) Uani 1 1 d . . . A 1


_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 N3 1.416(2) . ?
C1 N1 1.508(3) . ?
C1 N2 1.528(3) . ?
C2 N3 1.347(2) . ?
C2 C3 1.353(3) . ?
C3 N5 1.348(2) . ?
C3 N6 1.436(3) . ?
N1 O2 1.186(2) . ?
N1 O1 1.200(3) . ?
N2 O4 1.195(2) . ?
N2 O3 1.203(2) . ?
N3 N4 1.380(2) . ?
N4 N5 1.289(2) . ?
N6 O5 1.214(2) . ?
N6 O6 1.215(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
N3 C1 N1 113.75(16) . . ?
N3 C1 N2 112.52(16) . . ?
N1 C1 N2 102.39(14) . . ?
N3 C2 C3 102.63(16) . . ?
N5 C3 C2 111.59(17) . . ?
N5 C3 N6 121.01(16) . . ?
C2 C3 N6 127.40(17) . . ?
O2 N1 O1 126.3(2) . . ?
O2 N1 C1 118.10(18) . . ?
O1 N1 C1 115.6(2) . . ?
O4 N2 O3 127.0(2) . . ?
O4 N2 C1 117.92(17) . . ?
O3 N2 C1 115.07(19) . . ?
C2 N3 N4 110.87(15) . . ?
C2 N3 C1 132.58(16) . . ?
N4 N3 C1 116.34(15) . . ?
N5 N4 N3 106.86(15) . . ?
N4 N5 C3 108.04(15) . . ?
O5 N6 O6 125.31(18) . . ?
O5 N6 C3 116.70(17) . . ?
O6 N6 C3 117.99(17) . . ?

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
N3 C2 C3 N5 -0.5(2) . . . . ?
N3 C2 C3 N6 179.88(18) . . . . ?
N3 C1 N1 O2 -31.8(3) . . . . ?
N2 C1 N1 O2 89.9(2) . . . . ?
N3 C1 N1 O1 149.6(2) . . . . ?
N2 C1 N1 O1 -88.7(2) . . . . ?
N3 C1 N2 O4 22.7(3) . . . . ?
N1 C1 N2 O4 -99.8(2) . . . . ?
N3 C1 N2 O3 -158.54(18) . . . . ?
N1 C1 N2 O3 78.9(2) . . . . ?
C3 C2 N3 N4 0.2(2) . . . . ?
C3 C2 N3 C1 174.62(19) . . . . ?
N1 C1 N3 C2 52.8(3) . . . . ?
N2 C1 N3 C2 -63.1(3) . . . . ?
N1 C1 N3 N4 -133.03(17) . . . . ?
N2 C1 N3 N4 111.10(18) . . . . ?
C2 N3 N4 N5 0.2(2) . . . . ?
C1 N3 N4 N5 -175.19(16) . . . . ?
N3 N4 N5 C3 -0.6(2) . . . . ?
C2 C3 N5 N4 0.7(2) . . . . ?
N6 C3 N5 N4 -179.67(17) . . . . ?
N5 C3 N6 O5 171.50(18) . . . . ?
C2 C3 N6 O5 -9.0(3) . . . . ?
N5 C3 N6 O6 -9.0(3) . . . . ?
C2 C3 N6 O6 170.52(19) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_20211415_0m
_database_code_depnum_ccdc_archive 'CCDC 2224692'
loop_
_audit_author_name
_audit_author_address
Db
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_audit_creation_date             2021-09-24
_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 O6, H4 N O'
_chemical_formula_sum            'C3 H5 N7 O7'
_chemical_formula_weight         251.14
_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 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   4.8820(5)
_cell_length_b                   10.0306(10)
_cell_length_c                   8.9963(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.203(4)
_cell_angle_gamma                90
_cell_volume                     438.73(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1590
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.913
_cell_measurement_theta_min      3.049
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0919 before and 0.0549 after correction. The Ratio of minimum to maximum transmission is 0.8999. 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    1.901
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4532
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.869
_diffrn_reflns_theta_min         2.030
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.716
_reflns_Friedel_fraction_max     0.627
_reflns_number_gt                1360
_reflns_number_total             1686
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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    ?
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1686
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.100
_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)+(0.0411P)²+0.0087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0925
_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) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 N7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.8984(6) 0.2512(3) 0.3156(4) 0.0249(7) Uani 1 1 d . . . . .
O4 O 0.1147(6) 0.7072(3) 0.3134(4) 0.0237(7) Uani 1 1 d . . . . .
O7 O 0.8814(6) 0.7055(3) 0.6250(4) 0.0259(8) Uani 1 1 d . . . . .
O5 O 0.2435(6) 0.9016(3) 0.4022(4) 0.0235(7) Uani 1 1 d . . . . .
O6 O 0.7034(6) 0.9017(3) 0.5790(4) 0.0259(8) Uani 1 1 d . . . . .
O1 O 0.1017(6) 0.1674(3) 0.6490(4) 0.0253(7) Uani 1 1 d . . . . .
H1 H 0.201396 0.221622 0.607504 0.038 Uiso 1 1 calc GR . . . .
O2 O 0.5710(6) 0.1456(3) 0.4145(4) 0.0279(7) Uani 1 1 d . . . . .
N1 N 0.2755(7) 0.7768(3) 0.3969(4) 0.0165(8) Uani 1 1 d . . . . .
N4 N 0.3247(7) 0.4994(3) 0.5503(4) 0.0196(8) Uani 1 1 d . . . . .
N5 N 0.3812(7) 0.3751(3) 0.5233(5) 0.0184(8) Uani 1 1 d . . . . .
N2 N 0.6980(7) 0.7784(3) 0.5658(4) 0.0195(9) Uani 1 1 d . . . . .
N3 N 0.4982(8) 0.5747(3) 0.4720(5) 0.0174(6) Uani 1 1 d . . . . .
N6 N 0.6943(7) 0.2482(3) 0.3857(4) 0.0205(8) Uani 1 1 d . . . . .
N7 N 0.2518(7) 0.0509(3) 0.6858(4) 0.0220(8) Uani 1 1 d . . . . .
H7A H 0.296458 0.010436 0.600722 0.033 Uiso 1 1 calc GR . . . .
H7B H 0.148045 -0.005433 0.736731 0.033 Uiso 1 1 calc GR . . . .
H7C H 0.408214 0.072144 0.743711 0.033 Uiso 1 1 calc GR . . . .
C3 C 0.4848(10) 0.7145(3) 0.4790(6) 0.0161(7) Uani 1 1 d . . . . .
C2 C 0.6681(8) 0.4972(4) 0.4000(5) 0.0181(9) Uani 1 1 d . . . . .
H2 H 0.808566 0.523741 0.339764 0.022 Uiso 1 1 calc R . . . .
C1 C 0.5904(8) 0.3723(4) 0.4341(5) 0.0158(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
O3 N6 1.227(4) . ?
O4 N1 1.249(5) . ?
O7 N2 1.238(5) . ?
O5 N1 1.264(4) . ?
O6 N2 1.243(4) . ?
O1 H1 0.8400 . ?
O1 N7 1.402(4) . ?
O2 N6 1.232(4) . ?
N1 C3 1.358(6) . ?
N4 N5 1.304(4) . ?
N4 N3 1.376(5) . ?
N5 C1 1.355(5) . ?
N2 C3 1.399(6) . ?
N3 C3 1.405(4) . ?
N3 C2 1.345(5) . ?
N6 C1 1.427(5) . ?
N7 H7A 0.9100 . ?
N7 H7B 0.9100 . ?
N7 H7C 0.9100 . ?
C2 H2 0.9500 . ?
C2 C1 1.352(6) . ?

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 O1 H1 109.5 . . ?
O4 N1 O5 120.2(4) . . ?
O4 N1 C3 118.1(3) . . ?
O5 N1 C3 121.7(3) . . ?
N5 N4 N3 106.2(3) . . ?
N4 N5 C1 108.3(4) . . ?
O7 N2 O6 122.6(4) . . ?
O7 N2 C3 116.2(3) . . ?
O6 N2 C3 121.2(3) . . ?
N4 N3 C3 119.4(4) . . ?
C2 N3 N4 111.4(3) . . ?
C2 N3 C3 129.2(4) . . ?
O3 N6 O2 124.3(3) . . ?
O3 N6 C1 117.6(3) . . ?
O2 N6 C1 118.1(3) . . ?
O1 N7 H7A 109.5 . . ?
O1 N7 H7B 109.5 . . ?
O1 N7 H7C 109.5 . . ?
H7A N7 H7B 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
N1 C3 N2 125.3(3) . . ?
N1 C3 N3 118.1(4) . . ?
N2 C3 N3 116.6(4) . . ?
N3 C2 H2 128.4 . . ?
N3 C2 C1 103.2(3) . . ?
C1 C2 H2 128.4 . . ?
N5 C1 N6 120.4(4) . . ?
C2 C1 N5 110.9(4) . . ?
C2 C1 N6 128.6(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_my
_database_code_depnum_ccdc_archive 'CCDC 2224689'
loop_
_audit_author_name
_audit_author_address
Da
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_audit_creation_date             2021-09-24
_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 O6, H4 N O, H2 O'
_chemical_formula_sum            'C3 H7 N7 O8'
_chemical_formula_weight         269.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.4647(7)
_cell_length_b                   15.866(2)
_cell_length_c                   10.0270(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.745(4)
_cell_angle_gamma                90
_cell_volume                     1021.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1706
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.262
_cell_measurement_theta_min      2.414
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1085 before and 0.0666 after correction. The Ratio of minimum to maximum transmission is 0.8870. 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    1.750
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11428
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.415
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1329
_reflns_number_total             2097
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.345
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.007
_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)+(0.0455P)²+1.4593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1B = O1-H1A
 0.87 with sigma of 0.02
3.a Free rotating group:
 O1(H1A)
3.b Rotating group:
 N7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(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
O3 O 0.5457(3) 0.47749(14) 0.6861(2) 0.0275(5) Uani 1 1 d . . . . .
O5 O 0.7967(3) 0.44095(15) 0.5055(2) 0.0290(6) Uani 1 1 d . . . . .
O4 O 0.2690(3) 0.39801(15) 0.6792(2) 0.0291(6) Uani 1 1 d . . . . .
O6 O 0.7001(4) 0.33455(16) 0.3773(2) 0.0362(6) Uani 1 1 d . . . . .
O7 O -0.0694(4) 0.27562(16) 0.1717(2) 0.0340(6) Uani 1 1 d . . . . .
O2 O 0.9797(4) 0.52610(16) 0.8729(2) 0.0341(6) Uani 1 1 d . . . . .
H2 H 1.100846 0.538468 0.907014 0.051 Uiso 1 1 calc GR . . . .
O8 O -0.1325(4) 0.15884(16) 0.2729(3) 0.0376(6) Uani 1 1 d . . . . .
N2 N 0.4387(4) 0.41649(17) 0.6369(2) 0.0219(6) Uani 1 1 d . . . . .
N1 N 0.6745(4) 0.38251(17) 0.4714(3) 0.0239(6) Uani 1 1 d . . . . .
N5 N 0.2186(4) 0.31549(17) 0.3817(3) 0.0219(6) Uani 1 1 d . . . . .
N4 N 0.3658(4) 0.30390(16) 0.4855(3) 0.0228(6) Uani 1 1 d . . . . .
O1 O 1.3719(4) 0.56810(19) 0.9097(3) 0.0492(8) Uani 1 1 d D . . . .
H1A H 1.462666 0.534368 0.880517 0.074 Uiso 1 1 d DG . . . .
N3 N 0.3779(4) 0.22466(17) 0.5359(3) 0.0260(6) Uani 1 1 d . . . . .
N6 N -0.0351(4) 0.22437(19) 0.2625(3) 0.0267(7) Uani 1 1 d . . . . .
N7 N 0.9728(4) 0.52356(19) 0.7331(3) 0.0242(6) Uani 1 1 d . . . . .
H7A H 1.076038 0.491878 0.710263 0.029 Uiso 1 1 d GR . . . .
H7B H 0.852789 0.501461 0.697471 0.029 Uiso 1 1 d GR . . . .
C1 C 0.4976(5) 0.3684(2) 0.5357(3) 0.0206(7) Uani 1 1 d . . . . .
C2 C 0.1333(5) 0.2403(2) 0.3673(3) 0.0218(7) Uani 1 1 d . . . . .
C3 C 0.2280(5) 0.1840(2) 0.4615(3) 0.0280(8) Uani 1 1 d . . . . .
H3 H 0.191367 0.126452 0.470716 0.034 Uiso 1 1 calc R . . . .
H7C H 0.964(7) 0.580(3) 0.690(5) 0.074(15) Uiso 1 1 d . . . . .
H1B H 1.398(8) 0.6215(14) 0.902(5) 0.078(18) 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
O3 N2 1.256(3) . ?
O5 N1 1.240(3) . ?
O4 N2 1.257(3) . ?
O6 N1 1.239(3) . ?
O7 N6 1.221(3) . ?
O2 H2 0.8400 . ?
O2 N7 1.398(3) . ?
O8 N6 1.227(4) . ?
N2 C1 1.359(4) . ?
N1 C1 1.395(4) . ?
N5 N4 1.338(3) . ?
N5 C2 1.315(4) . ?
N4 N3 1.354(4) . ?
N4 C1 1.388(4) . ?
O1 H1A 0.8701 . ?
O1 H1B 0.870(19) . ?
N3 C3 1.320(4) . ?
N6 C2 1.444(4) . ?
N7 H7A 0.8870 . ?
N7 H7B 0.8871 . ?
N7 H7C 0.99(5) . ?
C2 C3 1.389(4) . ?
C3 H3 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
N7 O2 H2 109.5 . . ?
O3 N2 O4 120.6(3) . . ?
O3 N2 C1 122.4(2) . . ?
O4 N2 C1 117.0(3) . . ?
O5 N1 C1 121.5(3) . . ?
O6 N1 O5 122.1(3) . . ?
O6 N1 C1 116.4(3) . . ?
C2 N5 N4 102.2(3) . . ?
N5 N4 N3 115.0(2) . . ?
N5 N4 C1 122.1(3) . . ?
N3 N4 C1 122.9(2) . . ?
H1A O1 H1B 114.9 . . ?
C3 N3 N4 103.7(2) . . ?
O7 N6 O8 125.3(3) . . ?
O7 N6 C2 118.8(3) . . ?
O8 N6 C2 115.9(3) . . ?
O2 N7 H7A 109.8 . . ?
O2 N7 H7B 109.8 . . ?
O2 N7 H7C 114(3) . . ?
H7A N7 H7B 108.7 . . ?
H7A N7 H7C 113.8 . . ?
H7B N7 H7C 100.0 . . ?
N2 C1 N1 124.9(3) . . ?
N2 C1 N4 118.1(3) . . ?
N4 C1 N1 116.9(3) . . ?
N5 C2 N6 120.6(3) . . ?
N5 C2 C3 111.3(3) . . ?
C3 C2 N6 128.1(3) . . ?
N3 C3 C2 107.8(3) . . ?
N3 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
