# 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 2024

####################################################################### 
# 
# 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 2295355'
loop_
_audit_author_name
_audit_author_address
'Shaoqing Wang'
;Beijing Insititute of Technology
China
;
_audit_update_record             
;
2023-09-16 deposited with the CCDC.	2024-04-15 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            'C5 H6 N10 O4'
_chemical_formula_weight         270.20

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                   11.6674(8)
_cell_length_b                   7.3765(5)
_cell_length_c                   11.8952(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.965(2)
_cell_angle_gamma                90
_cell_volume                     1021.31(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4508
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      24.45

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_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            10923
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_full        25.028
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1784
_reflns_number_gt                1332
_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)+(0.0596P)²+0.5373P] 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         1784
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1078
_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 0.3793(2) 0.2293(3) 0.07272(18) 0.0364(6) Uani 1 1 d . . . . .
C2 C 0.50784(19) 0.1219(3) 0.18165(18) 0.0343(6) Uani 1 1 d . . . . .
C3 C 0.3784(2) 0.0524(3) 0.33868(18) 0.0381(6) Uani 1 1 d . . . . .
H3A H 0.3103 -0.0222 0.3254 0.046 Uiso 1 1 calc R U . . .
H3B H 0.4405 -0.0257 0.3676 0.046 Uiso 1 1 calc R U . . .
C4 C 0.25617(19) 0.2593(3) 0.45121(18) 0.0351(6) Uani 1 1 d . . . . .
C5 C 0.38828(19) 0.3505(3) 0.56074(18) 0.0330(6) Uani 1 1 d . . . . .
N1 N 0.3225(2) 0.3048(3) -0.02906(17) 0.0460(6) Uani 1 1 d . . . . .
N2 N 0.49111(16) 0.1851(3) 0.07702(15) 0.0383(5) Uani 1 1 d . . . . .
N3 N 0.60598(17) 0.0531(3) 0.22938(18) 0.0495(6) Uani 1 1 d . . . . .
H3C H 0.6660 0.0469 0.1914 0.059 Uiso 1 1 calc R U . . .
H3D H 0.6089 0.0153 0.2979 0.059 Uiso 1 1 calc R U . . .
N4 N 0.40799(15) 0.1295(3) 0.23307(14) 0.0340(5) Uani 1 1 d . . . . .
N5 N 0.32264(16) 0.2020(3) 0.16170(15) 0.0382(5) Uani 1 1 d . . . . .
N6 N 0.35706(15) 0.1873(3) 0.42246(14) 0.0335(5) Uani 1 1 d . . . . .
N7 N 0.44536(16) 0.2473(3) 0.49534(15) 0.0362(5) Uani 1 1 d . . . . .
N8 N 0.44832(19) 0.4464(3) 0.65335(16) 0.0420(5) Uani 1 1 d . . . . .
N9 N 0.27467(16) 0.3667(3) 0.54071(15) 0.0368(5) Uani 1 1 d . . . . .
N10 N 0.15398(17) 0.2257(3) 0.39811(18) 0.0549(7) Uani 1 1 d . . . . .
H10A H 0.0932 0.2753 0.4212 0.066 Uiso 1 1 calc R U . . .
H10B H 0.1489 0.1546 0.3407 0.066 Uiso 1 1 calc R U . . .
O1 O 0.37875(19) 0.3166(4) -0.11035(16) 0.0773(7) Uani 1 1 d . . . . .
O2 O 0.22176(17) 0.3491(3) -0.02744(15) 0.0593(6) Uani 1 1 d . . . . .
O3 O 0.39363(18) 0.5564(3) 0.70321(16) 0.0600(6) Uani 1 1 d . . . . .
O4 O 0.55028(17) 0.4118(3) 0.67464(15) 0.0621(6) 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 N5 1.302(3) . ?
C1 N2 1.342(3) . ?
C1 N1 1.451(3) . ?
C2 N2 1.331(3) . ?
C2 N3 1.342(3) . ?
C2 N4 1.354(3) . ?
C3 N6 1.442(3) . ?
C3 N4 1.443(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N9 1.333(3) . ?
C4 N10 1.333(3) . ?
C4 N6 1.357(3) . ?
C5 N7 1.304(3) . ?
C5 N9 1.336(3) . ?
C5 N8 1.448(3) . ?
N1 O1 1.209(3) . ?
N1 O2 1.221(3) . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?
N4 N5 1.372(3) . ?
N6 N7 1.373(3) . ?
N8 O3 1.212(3) . ?
N8 O4 1.226(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 C1 N2 118.6(2) . . ?
N5 C1 N1 120.6(2) . . ?
N2 C1 N1 120.8(2) . . ?
N2 C2 N3 126.4(2) . . ?
N2 C2 N4 109.4(2) . . ?
N3 C2 N4 124.1(2) . . ?
N6 C3 N4 113.1(2) . . ?
N6 C3 H3A 109.0 . . ?
N4 C3 H3A 109.0 . . ?
N6 C3 H3B 109.0 . . ?
N4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N9 C4 N10 125.4(2) . . ?
N9 C4 N6 109.80(19) . . ?
N10 C4 N6 124.8(2) . . ?
N7 C5 N9 119.2(2) . . ?
N7 C5 N8 119.9(2) . . ?
N9 C5 N8 120.9(2) . . ?
O1 N1 O2 124.7(2) . . ?
O1 N1 C1 117.0(2) . . ?
O2 N1 C1 118.3(2) . . ?
C2 N2 C1 101.54(18) . . ?
C2 N3 H3C 120.0 . . ?
C2 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?
C2 N4 N5 110.32(18) . . ?
C2 N4 C3 130.0(2) . . ?
N5 N4 C3 119.04(18) . . ?
C1 N5 N4 100.11(17) . . ?
C4 N6 N7 109.93(18) . . ?
C4 N6 C3 129.68(19) . . ?
N7 N6 C3 120.07(18) . . ?
C5 N7 N6 99.97(17) . . ?
O3 N8 O4 125.1(2) . . ?
O3 N8 C5 117.1(2) . . ?
O4 N8 C5 117.8(2) . . ?
C4 N9 C5 101.14(18) . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C1 N1 O1 -175.9(2) . . . . ?
N2 C1 N1 O1 3.8(4) . . . . ?
N5 C1 N1 O2 3.1(4) . . . . ?
N2 C1 N1 O2 -177.3(2) . . . . ?
N3 C2 N2 C1 177.8(2) . . . . ?
N4 C2 N2 C1 0.5(3) . . . . ?
N5 C1 N2 C2 0.0(3) . . . . ?
N1 C1 N2 C2 -179.6(2) . . . . ?
N2 C2 N4 N5 -0.9(3) . . . . ?
N3 C2 N4 N5 -178.3(2) . . . . ?
N2 C2 N4 C3 169.4(2) . . . . ?
N3 C2 N4 C3 -8.0(4) . . . . ?
N6 C3 N4 C2 113.7(3) . . . . ?
N6 C3 N4 N5 -76.7(3) . . . . ?
N2 C1 N5 N4 -0.5(3) . . . . ?
N1 C1 N5 N4 179.1(2) . . . . ?
C2 N4 N5 C1 0.8(2) . . . . ?
C3 N4 N5 C1 -170.7(2) . . . . ?
N9 C4 N6 N7 0.5(3) . . . . ?
N10 C4 N6 N7 -179.0(2) . . . . ?
N9 C4 N6 C3 173.8(2) . . . . ?
N10 C4 N6 C3 -5.6(4) . . . . ?
N4 C3 N6 C4 96.4(3) . . . . ?
N4 C3 N6 N7 -90.8(2) . . . . ?
N9 C5 N7 N6 -0.1(3) . . . . ?
N8 C5 N7 N6 -179.80(19) . . . . ?
C4 N6 N7 C5 -0.2(2) . . . . ?
C3 N6 N7 C5 -174.33(19) . . . . ?
N7 C5 N8 O3 171.7(2) . . . . ?
N9 C5 N8 O3 -8.1(3) . . . . ?
N7 C5 N8 O4 -7.7(3) . . . . ?
N9 C5 N8 O4 172.6(2) . . . . ?
N10 C4 N9 C5 179.0(2) . . . . ?
N6 C4 N9 C5 -0.5(2) . . . . ?
N7 C5 N9 C4 0.4(3) . . . . ?
N8 C5 N9 C4 -179.9(2) . . . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.047

