# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2027401'
loop_
_audit_author_name
_audit_author_address
'Dongxu Chen'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-08-23 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         'C5 H6 N10 O3, 2(H2 O)'
_chemical_formula_sum            'C5 H10 N10 O5'
_chemical_formula_weight         290.23

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                   9.9197(14)
_cell_length_b                   7.1740(7)
_cell_length_c                   16.673(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.745(4)
_cell_angle_gamma                90
_cell_volume                     1136.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    849
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.02

_exptl_crystal_description       sheet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 2 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6638
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.113
_diffrn_reflns_theta_max         25.643
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2119
_reflns_number_gt                1232
_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       APEX3
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SHELXS-2014/7
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  olex
_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)+(0.0438P)²+0.5497P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     224
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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 1.0113(3) 0.2216(5) 1.0265(2) 0.0231(8) Uani 1 1 d . . . . .
C2 C 0.8293(3) 0.2971(5) 0.9320(2) 0.0247(8) Uani 1 1 d . . . . .
C4 C 0.6789(4) 0.3299(5) 0.8871(2) 0.0300(9) Uani 1 1 d . . . . .
C6 C 0.4177(4) 0.3020(6) 0.7217(2) 0.0321(9) Uani 1 1 d . . . . .
C7 C 0.4578(4) 0.6015(6) 0.7459(2) 0.0376(10) Uani 1 1 d . . . . .
H7 H 0.5050 0.7149 0.7659 0.045 Uiso 1 1 calc R U . . .
N1 N 0.9306(3) 0.3438(4) 0.89846(17) 0.0257(7) Uani 1 1 d . . . . .
N2 N 1.0476(3) 0.2953(4) 0.96110(18) 0.0264(7) Uani 1 1 d D . . . .
H2A H 1.133(3) 0.317(5) 0.958(2) 0.032 Uiso 1 1 d D U . . .
N3 N 0.8706(3) 0.2226(4) 1.01012(17) 0.0257(7) Uani 1 1 d . . . . .
N4 N 1.0921(3) 0.1522(4) 1.10241(18) 0.0268(7) Uani 1 1 d . . . . .
N5 N 1.2281(3) 0.1583(4) 1.11677(19) 0.0295(7) Uani 1 1 d . . . . .
N6 N 0.6531(3) 0.3885(4) 0.80685(18) 0.0305(7) Uani 1 1 d D . . . .
H6A H 0.712(3) 0.388(5) 0.776(2) 0.037 Uiso 1 1 d D U . . .
N7 N 0.3275(3) 0.5894(5) 0.6978(2) 0.0445(9) Uani 1 1 d . . . . .
N8 N 0.3037(3) 0.4007(5) 0.6843(2) 0.0366(8) Uani 1 1 d D . . . .
H8A H 0.223(3) 0.380(5) 0.6433(19) 0.044 Uiso 1 1 d D U . . .
N9 N 0.5152(3) 0.4301(4) 0.76297(18) 0.0308(7) Uani 1 1 d . . . . .
N10 N 0.4361(3) 0.1201(5) 0.7225(2) 0.0403(8) Uani 1 1 d D . . . .
H10A H 0.515(3) 0.068(5) 0.753(2) 0.048 Uiso 1 1 d D U . . .
H10B H 0.370(3) 0.053(5) 0.687(2) 0.048 Uiso 1 1 d D U . . .
O1 O 1.2885(2) 0.2282(4) 1.06667(16) 0.0397(7) Uani 1 1 d . . . . .
O2 O 1.3037(2) 0.0921(4) 1.18736(15) 0.0352(6) Uani 1 1 d . . . . .
O3 O 0.5827(3) 0.3065(4) 0.91892(16) 0.0429(7) Uani 1 1 d . . . . .
O4 O 0.2251(3) 0.9155(4) 0.6044(2) 0.0487(8) Uani 1 1 d D . . . .
H4C H 0.210(5) 0.813(4) 0.624(3) 0.058 Uiso 1 1 d D U . . .
H4D H 0.162(4) 0.991(5) 0.584(3) 0.058 Uiso 1 1 d D U . . .
O5 O 1.5720(5) 0.2417(15) 1.0772(3) 0.046(2) Uani 0.75(2) 1 d D U P A 1
H5C H 1.487(3) 0.251(9) 1.073(4) 0.055 Uiso 0.75(2) 1 d D U P A 1
H5D H 1.578(8) 0.251(9) 1.029(2) 0.055 Uiso 0.75(2) 1 d D U P A 1
O5' O 1.5606(18) 0.120(5) 1.0644(13) 0.066(6) Uani 0.25(2) 1 d D U P A 2
H5'C H 1.482(9) 0.09(3) 1.066(13) 0.079 Uiso 0.25(2) 1 d D U P A 2
H5'D H 1.56(3) 0.19(3) 1.032(9) 0.079 Uiso 0.25(2) 1 d D U P A 2


_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 1.342(4) . ?
C1 N2 1.351(4) . ?
C1 N4 1.381(4) . ?
C2 N1 1.327(4) . ?
C2 N3 1.357(4) . ?
C2 C4 1.482(5) . ?
C4 O3 1.229(4) . ?
C4 N6 1.355(4) . ?
C6 N10 1.317(5) . ?
C6 N8 1.328(5) . ?
C6 N9 1.367(5) . ?
C7 N7 1.313(5) . ?
C7 N9 1.351(5) . ?
C7 H7 0.9500 . ?
N1 N2 1.364(4) . ?
N2 H2A 0.88(2) . ?
N4 N5 1.301(4) . ?
N5 O1 1.264(4) . ?
N5 O2 1.290(4) . ?
N6 N9 1.385(4) . ?
N6 H6A 0.88(2) . ?
N7 N8 1.381(4) . ?
N8 H8A 0.90(2) . ?
N10 H10A 0.88(2) . ?
N10 H10B 0.89(2) . ?
O4 H4C 0.842(19) . ?
O4 H4D 0.820(19) . ?
O5 H5C 0.83(2) . ?
O5 H5D 0.83(2) . ?
O5' H5'C 0.82(2) . ?
O5' H5'D 0.7(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 N2 109.7(3) . . ?
N3 C1 N4 118.9(3) . . ?
N2 C1 N4 131.4(3) . . ?
N1 C2 N3 116.6(3) . . ?
N1 C2 C4 121.4(3) . . ?
N3 C2 C4 121.9(3) . . ?
O3 C4 N6 121.3(3) . . ?
O3 C4 C2 123.6(3) . . ?
N6 C4 C2 115.1(3) . . ?
N10 C6 N8 129.0(4) . . ?
N10 C6 N9 125.8(3) . . ?
N8 C6 N9 105.1(3) . . ?
N7 C7 N9 110.4(3) . . ?
N7 C7 H7 124.8 . . ?
N9 C7 H7 124.8 . . ?
C2 N1 N2 101.2(3) . . ?
C1 N2 N1 110.6(3) . . ?
C1 N2 H2A 127(2) . . ?
N1 N2 H2A 122(2) . . ?
C1 N3 C2 101.9(3) . . ?
N5 N4 C1 117.0(3) . . ?
O1 N5 O2 119.2(3) . . ?
O1 N5 N4 123.7(3) . . ?
O2 N5 N4 117.1(3) . . ?
C4 N6 N9 117.7(3) . . ?
C4 N6 H6A 127(2) . . ?
N9 N6 H6A 115(2) . . ?
C7 N7 N8 104.9(3) . . ?
C6 N8 N7 111.3(3) . . ?
C6 N8 H8A 136(3) . . ?
N7 N8 H8A 111(3) . . ?
C7 N9 C6 108.2(3) . . ?
C7 N9 N6 126.9(3) . . ?
C6 N9 N6 124.7(3) . . ?
C6 N10 H10A 122(3) . . ?
C6 N10 H10B 117(3) . . ?
H10A N10 H10B 121(4) . . ?
H4C O4 H4D 122(5) . . ?
H5C O5 H5D 105(7) . . ?
H5'C O5' H5'D 114(10) . . ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.060

