# 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 2019

####################################################################### 
# 
# 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 1847087'
loop_
_audit_author_name
_audit_author_address
'hualin xiong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-07-02 deposited with the CCDC.	2019-08-05 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         'C4 H2 N8 O10'
_chemical_formula_sum            'C4 H2 N8 O10'
_chemical_formula_weight         322.14

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.7073(4)
_cell_length_b                   8.8246(7)
_cell_length_c                   18.6187(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1102.03(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3778
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      26.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_T_max  0.7454
_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 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12743
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.181
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2249
_reflns_number_gt                1812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_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       crysalispro
_computing_cell_refinement       'SCALE3 ABSPACK'
_computing_data_reduction        'SCALE3 ABSPACK'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0262P)²+0.3389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2249
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.2917(4) 0.4510(3) 0.87534(16) 0.0143(7) Uani 1 1 d . . . . .
C2 C 0.2725(4) 0.5953(4) 0.84729(15) 0.0128(7) Uani 1 1 d . . . . .
C3 C 0.0964(4) 0.6546(4) 0.87823(15) 0.0140(7) Uani 1 1 d . . . . .
C4 C 0.0054(4) 0.8065(3) 0.87241(15) 0.0144(7) Uani 1 1 d . . . . .
N1 N 0.0149(4) 0.5541(3) 0.92193(13) 0.0168(6) Uani 1 1 d . . . . .
N2 N 0.1338(4) 0.4312(3) 0.91825(15) 0.0173(6) Uani 1 1 d . . . . .
H2A H 0.110(5) 0.362(4) 0.9451(19) 0.021 Uiso 1 1 d . U . . .
N3 N 0.4343(4) 0.3443(3) 0.86026(14) 0.0201(6) Uani 1 1 d . . . . .
H3A H 0.500(5) 0.354(4) 0.8240(18) 0.024 Uiso 1 1 d . U . . .
N4 N 0.5204(4) 0.2566(3) 0.91236(15) 0.0258(7) Uani 1 1 d . . . . .
N5 N 0.4038(4) 0.6667(3) 0.79808(14) 0.0165(6) Uani 1 1 d . . . . .
N6 N -0.0899(4) 0.8400(3) 0.79915(14) 0.0199(6) Uani 1 1 d . . . . .
N7 N -0.1622(4) 0.8228(3) 0.92814(15) 0.0204(6) Uani 1 1 d . . . . .
N8 N 0.1550(4) 0.9350(3) 0.88914(14) 0.0209(6) Uani 1 1 d . . . . .
O1 O 0.4415(4) 0.2579(3) 0.97203(12) 0.0323(6) Uani 1 1 d . . . . .
O2 O 0.6639(4) 0.1828(3) 0.89434(14) 0.0448(8) Uani 1 1 d . . . . .
O3 O 0.5476(3) 0.5950(2) 0.77576(12) 0.0231(5) Uani 1 1 d . . . . .
O4 O 0.3658(3) 0.7988(2) 0.78031(12) 0.0222(5) Uani 1 1 d . . . . .
O5 O -0.2122(4) 0.9414(3) 0.79799(13) 0.0349(6) Uani 1 1 d . . . . .
O6 O -0.0367(4) 0.7621(3) 0.74952(12) 0.0318(6) Uani 1 1 d . . . . .
O7 O -0.1228(4) 0.8963(3) 0.98128(12) 0.0306(6) Uani 1 1 d . . . . .
O8 O -0.3150(3) 0.7565(3) 0.91441(13) 0.0316(6) Uani 1 1 d . . . . .
O9 O 0.1238(4) 1.0578(3) 0.86250(14) 0.0380(7) Uani 1 1 d . . . . .
O10 O 0.2878(3) 0.9007(3) 0.92995(13) 0.0289(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 N2 1.338(4) . ?
C1 N3 1.371(4) . ?
C1 C2 1.382(4) . ?
C2 C3 1.414(4) . ?
C2 N5 1.419(4) . ?
C3 N1 1.322(4) . ?
C3 C4 1.477(4) . ?
C4 N6 1.535(4) . ?
C4 N7 1.536(4) . ?
C4 N8 1.546(4) . ?
N1 N2 1.348(3) . ?
N2 H2A 0.80(4) . ?
N3 N4 1.368(4) . ?
N3 H3A 0.81(3) . ?
N4 O2 1.210(4) . ?
N4 O1 1.230(3) . ?
N5 O3 1.226(3) . ?
N5 O4 1.239(3) . ?
N6 O6 1.205(3) . ?
N6 O5 1.215(3) . ?
N7 O8 1.208(3) . ?
N7 O7 1.212(3) . ?
N8 O10 1.209(3) . ?
N8 O9 1.210(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 N3 125.8(3) . . ?
N2 C1 C2 105.8(3) . . ?
N3 C1 C2 128.3(3) . . ?
C1 C2 C3 105.3(3) . . ?
C1 C2 N5 126.5(3) . . ?
C3 C2 N5 128.1(3) . . ?
N1 C3 C2 110.4(3) . . ?
N1 C3 C4 118.9(3) . . ?
C2 C3 C4 130.6(3) . . ?
C3 C4 N6 114.3(3) . . ?
C3 C4 N7 109.7(2) . . ?
N6 C4 N7 106.1(2) . . ?
C3 C4 N8 112.5(2) . . ?
N6 C4 N8 107.9(2) . . ?
N7 C4 N8 105.7(2) . . ?
C3 N1 N2 105.3(2) . . ?
C1 N2 N1 113.2(3) . . ?
C1 N2 H2A 129(2) . . ?
N1 N2 H2A 117(3) . . ?
N4 N3 C1 122.5(3) . . ?
N4 N3 H3A 115(3) . . ?
C1 N3 H3A 119(3) . . ?
O2 N4 O1 126.7(3) . . ?
O2 N4 N3 116.3(3) . . ?
O1 N4 N3 117.0(3) . . ?
O3 N5 O4 123.9(3) . . ?
O3 N5 C2 118.6(3) . . ?
O4 N5 C2 117.6(3) . . ?
O6 N6 O5 127.3(3) . . ?
O6 N6 C4 116.6(3) . . ?
O5 N6 C4 116.0(3) . . ?
O8 N7 O7 128.1(3) . . ?
O8 N7 C4 115.6(3) . . ?
O7 N7 C4 116.2(3) . . ?
O10 N8 O9 127.5(3) . . ?
O10 N8 C4 114.9(3) . . ?
O9 N8 C4 117.5(3) . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.051

