# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_bwn19064
_database_code_depnum_ccdc_archive 'CCDC 1946324'
loop_
_audit_author_name
_audit_author_address
'Jianguo Zhang'
;BIT
China
;
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-03-13
_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        'dihydraine tetranitroethide'
_chemical_formula_moiety         '2(C N2 O4), 2(H5 N2)'
_chemical_formula_sum            'C2 H10 N8 O8'
_chemical_formula_weight         274.18
_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           15
_space_group_name_H-M_alt        'C 1 2/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'
'-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                   16.946(3)
_cell_length_b                   9.3354(19)
_cell_length_c                   14.414(3)
_cell_angle_alpha                90
_cell_angle_beta                 120.28(3)
_cell_angle_gamma                90
_cell_volume                     1969.1(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4507
_cell_measurement_theta_min      1.6360
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5853
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.588
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'multiwire proportional'
_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                1978
_reflns_number_total             2248
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.261
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.120
_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)+(0.0454P)²+3.0230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H) groups
2.a Riding coordinates:
 N5(H5A,H5B,H5C), N6(H6A,H6B), N7(H7A,H7B,H7C), N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   difmap
_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
O7 O 0.66147(10) 0.63302(16) 0.45644(12) 0.0232(3) Uani 1 1 d . . . A 2
O5 O 0.56857(11) 0.85917(17) 0.18202(12) 0.0269(4) Uani 1 1 d . . . . .
O8 O 0.52017(10) 0.56984(16) 0.39703(12) 0.0242(3) Uani 1 1 d . . . . .
O6 O 0.68728(10) 0.81744(17) 0.33827(13) 0.0278(4) Uani 1 1 d . . . B 1
N4 N 0.57873(11) 0.63624(18) 0.38411(13) 0.0175(4) Uani 1 1 d . . . A 2
N3 N 0.60520(11) 0.79849(18) 0.27205(14) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.54766(12) 0.7103(2) 0.28940(15) 0.0164(4) Uani 1 1 d . . . . .
O2 O 0.37819(10) 0.37920(16) 0.18362(13) 0.0242(3) Uani 1 1 d . . . C 1
O3 O 0.60062(10) 0.07287(16) 0.39228(12) 0.0244(4) Uani 1 1 d . . . . .
O1 O 0.38010(11) 0.31631(16) 0.32981(13) 0.0273(4) Uani 1 1 d . . . . .
O4 O 0.51540(11) 0.14608(18) 0.45634(12) 0.0268(4) Uani 1 1 d . . . . .
N2 N 0.53308(11) 0.14436(17) 0.38247(14) 0.0178(4) Uani 1 1 d . . . . .
N5 N 0.67276(12) 0.89312(19) 0.57319(14) 0.0199(4) Uani 1 1 d . . . . .
H5A H 0.643534 0.936303 0.513275 0.024 Uiso 1 1 d R . . . .
H5B H 0.714444 0.844163 0.571805 0.024 Uiso 1 1 d R . . . .
H5C H 0.634454 0.837263 0.576125 0.024 Uiso 1 1 d R . . . .
N1 N 0.41215(11) 0.30786(17) 0.26887(14) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.48472(13) 0.2199(2) 0.28817(16) 0.0165(4) Uani 1 1 d . . . . .
N6 N 0.71537(13) 0.97994(19) 0.66943(15) 0.0241(4) Uani 1 1 d . . . . .
H6A H 0.672603 1.030946 0.666446 0.029 Uiso 1 1 d R . . . .
H6B H 0.753993 1.037326 0.668676 0.029 Uiso 1 1 d R . . . .
N7 N 0.34802(15) 0.5962(2) 0.39689(17) 0.0325(5) Uani 1 1 d . . . . .
H7A H 0.314780 0.574189 0.330976 0.039 Uiso 1 1 d R . . . .
H7B H 0.392950 0.650419 0.410686 0.039 Uiso 1 1 d R . . . .
H7C H 0.364570 0.515909 0.428826 0.039 Uiso 1 1 d R . . . .
N8 N 0.29014(14) 0.6684(2) 0.42666(18) 0.0336(5) Uani 1 1 d . . . . .
H8A H 0.241799 0.619526 0.406169 0.040 Uiso 1 1 d R . . . .
H8B H 0.312259 0.656626 0.493759 0.040 Uiso 1 1 d 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
O7 N4 1.257(2) . ?
O5 N3 1.256(2) . ?
O8 N4 1.261(2) . ?
O6 N3 1.240(2) . ?
N4 C2 1.376(3) . ?
N3 C2 1.392(2) . ?
C2 C2 1.431(4) 2_655 ?
O2 N1 1.254(2) . ?
O3 N2 1.270(2) . ?
O1 N1 1.247(2) . ?
O4 N2 1.243(2) . ?
N2 C1 1.376(3) . ?
N5 N6 1.446(3) . ?
N1 C1 1.385(2) . ?
C1 C1 1.433(4) 2_655 ?
N7 N8 1.423(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
O7 N4 O8 119.84(16) . . ?
O7 N4 C2 122.93(17) . . ?
O8 N4 C2 117.22(17) . . ?
O5 N3 C2 115.25(17) . . ?
O6 N3 O5 120.59(17) . . ?
O6 N3 C2 124.16(17) . . ?
N4 C2 N3 121.55(17) . . ?
N3 C2 C2 118.03(17) . 2_655 ?
O3 N2 C1 115.70(16) . . ?
O4 N2 O3 120.29(17) . . ?
O4 N2 C1 123.98(16) . . ?
O2 N1 C1 115.72(16) . . ?
O1 N1 O2 120.62(16) . . ?
O1 N1 C1 123.65(17) . . ?
N2 C1 N1 121.89(17) . . ?
N2 C1 C1 119.53(18) . 2_655 ?
N1 C1 C1 118.28(18) . 2_655 ?

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
O7 N4 C2 N3 -6.4(3) . . . . ?
O7 N4 C2 C2 -179.58(15) . . . 2_655 ?
O5 N3 C2 N4 179.52(17) . . . . ?
O5 N3 C2 C2 -7.2(2) . . . 2_655 ?
O8 N4 C2 N3 173.40(17) . . . . ?
O8 N4 C2 C2 0.2(2) . . . 2_655 ?
O6 N3 C2 C2 173.51(17) . . . 2_655 ?
O2 N1 C1 N2 174.76(17) . . . . ?
O2 N1 C1 C1 1.1(3) . . . 2_655 ?
O3 N2 C1 N1 -176.87(17) . . . . ?
O3 N2 C1 C1 -3.3(2) . . . 2_655 ?
O1 N1 C1 N2 -6.4(3) . . . . ?
O1 N1 C1 C1 -179.98(17) . . . 2_655 ?
O4 N2 C1 N1 1.4(3) . . . . ?
O4 N2 C1 C1 174.90(16) . . . 2_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
