# 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_yzw
_database_code_depnum_ccdc_archive 'CCDC 1580504'
loop_
_audit_author_name
_audit_author_address
'DONG CHEN'
;China Academy of Engineering Physics
China
;
_audit_update_record             
;
2018-06-24 deposited with the CCDC.	2019-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'Biscarbohydrazide bis[3-(5-nitroimino-1,2,4-triazolate)]'
_chemical_name_common            DCBNT
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N10 O4, 2(C H7 N4 O)'
_chemical_formula_sum            'C6 H16 N18 O6'
_chemical_formula_weight         436.37

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                   4.8647(3)
_cell_length_b                   25.2903(17)
_cell_length_c                   6.7166(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.765(7)
_cell_angle_gamma                90
_cell_volume                     814.36(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1506
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2390
_cell_measurement_theta_min      4.3010

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5101
_diffrn_reflns_av_unetI/netI     0.1974
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.181
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1660
_reflns_number_gt                1029
_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-2017/1 (Sheldrick, 2017)'
_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)+(0.0455P)²+2.4695P] 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         1660
_refine_ls_number_parameters     144
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1613
_refine_ls_R_factor_gt           0.0978
_refine_ls_wR_factor_ref         0.1881
_refine_ls_wR_factor_gt          0.1702
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.091
_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
O1 O 1.0717(8) 0.58405(15) -0.0146(6) 0.0407(11) Uani 1 1 d . . . . .
O2 O 1.3738(7) 0.63765(14) 0.1582(6) 0.0380(10) Uani 1 1 d . . . . .
N1 N 0.7742(8) 0.55003(15) 0.4870(6) 0.0219(9) Uani 1 1 d . . . . .
N2 N 0.5545(8) 0.49693(16) 0.2402(6) 0.0248(10) Uani 1 1 d . . . . .
N3 N 0.7458(9) 0.52845(16) 0.1707(6) 0.0269(10) Uani 1 1 d . . . . .
H3 H 0.779420 0.528036 0.049064 0.032 Uiso 1 1 calc R U . . .
N4 N 1.0820(8) 0.59650(16) 0.3199(6) 0.0248(10) Uani 1 1 d . . . . .
N5 N 1.1734(9) 0.60560(16) 0.1496(7) 0.0275(10) Uani 1 1 d . . . . .
C1 C 0.8719(10) 0.55957(17) 0.3153(7) 0.0187(10) Uani 1 1 d . . . . .
C2 C 0.5817(9) 0.51158(17) 0.4291(7) 0.0202(10) Uani 1 1 d . . . . .
O3 O 0.8315(8) 0.68320(16) 0.6611(9) 0.0690(17) Uani 1 1 d . . . . .
N6 N 0.3914(9) 0.67965(16) 0.7077(8) 0.0377(12) Uani 1 1 d . . . . .
H6 H 0.244613 0.695328 0.733629 0.045 Uiso 1 1 calc R U . . .
N7 N 0.4026(8) 0.62416(15) 0.6929(6) 0.0261(10) Uani 1 1 d . . . . .
H7A H 0.347201 0.609638 0.800131 0.031 Uiso 1 1 calc R U . . .
H7B H 0.576790 0.614186 0.688075 0.031 Uiso 1 1 calc R U . . .
H7C H 0.290845 0.613595 0.581119 0.022(14) Uiso 1 1 calc R . . . .
N8 N 0.5907(10) 0.75885(18) 0.6767(10) 0.0532(16) Uani 1 1 d . . . . .
H8 H 0.732139 0.778173 0.663952 0.064 Uiso 1 1 calc R U . . .
N9 N 0.3346(11) 0.78316(18) 0.6936(9) 0.0451(13) Uani 1 1 d D . . . .
H9A H 0.366(11) 0.8002(18) 0.812(3) 0.054 Uiso 1 1 d D U . . .
H9B H 0.311(12) 0.7973(19) 0.569(3) 0.054 Uiso 1 1 d D U . . .
C3 C 0.6162(11) 0.7071(2) 0.6802(9) 0.0338(13) 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
O1 N5 1.255(5) . ?
O2 N5 1.261(5) . ?
N1 C1 1.342(6) . ?
N1 C2 1.360(6) . ?
N2 C2 1.307(6) . ?
N2 N3 1.366(5) . ?
N3 C1 1.318(6) . ?
N3 H3 0.8600 . ?
N4 N5 1.316(6) . ?
N4 C1 1.381(6) . ?
C2 C2 1.462(9) 3_666 ?
O3 C3 1.234(6) . ?
N6 C3 1.334(6) . ?
N6 N7 1.409(5) . ?
N6 H6 0.8600 . ?
N7 H7A 0.8900 . ?
N7 H7B 0.8900 . ?
N7 H7C 0.8900 . ?
N8 C3 1.315(7) . ?
N8 N9 1.411(7) . ?
N8 H8 0.8600 . ?
N9 H9A 0.894(10) . ?
N9 H9B 0.899(9) . ?

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
C1 N1 C2 102.1(4) . . ?
C2 N2 N3 101.7(4) . . ?
C1 N3 N2 110.8(4) . . ?
C1 N3 H3 124.6 . . ?
N2 N3 H3 124.6 . . ?
N5 N4 C1 117.2(4) . . ?
O1 N5 O2 120.4(4) . . ?
O1 N5 N4 123.2(4) . . ?
O2 N5 N4 116.4(4) . . ?
N3 C1 N1 109.7(4) . . ?
N3 C1 N4 132.1(4) . . ?
N1 C1 N4 118.1(4) . . ?
N2 C2 N1 115.6(4) . . ?
N2 C2 C2 122.8(5) . 3_666 ?
N1 C2 C2 121.6(5) . 3_666 ?
C3 N6 N7 117.8(4) . . ?
C3 N6 H6 121.1 . . ?
N7 N6 H6 121.1 . . ?
N6 N7 H7A 109.5 . . ?
N6 N7 H7B 109.5 . . ?
H7A N7 H7B 109.5 . . ?
N6 N7 H7C 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
C3 N8 N9 121.0(5) . . ?
C3 N8 H8 119.5 . . ?
N9 N8 H8 119.5 . . ?
N8 N9 H9A 105(4) . . ?
N8 N9 H9B 94(3) . . ?
H9A N9 H9B 128(4) . . ?
O3 C3 N8 124.3(5) . . ?
O3 C3 N6 119.4(5) . . ?
N8 C3 N6 116.3(5) . . ?

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
C2 N2 N3 C1 -0.5(5) . . . . ?
C1 N4 N5 O1 2.9(7) . . . . ?
C1 N4 N5 O2 -176.9(4) . . . . ?
N2 N3 C1 N1 0.7(6) . . . . ?
N2 N3 C1 N4 177.9(5) . . . . ?
C2 N1 C1 N3 -0.5(5) . . . . ?
C2 N1 C1 N4 -178.2(4) . . . . ?
N5 N4 C1 N3 3.4(8) . . . . ?
N5 N4 C1 N1 -179.5(4) . . . . ?
N3 N2 C2 N1 0.2(5) . . . . ?
N3 N2 C2 C2 -179.6(5) . . . 3_666 ?
C1 N1 C2 N2 0.2(5) . . . . ?
C1 N1 C2 C2 -180.0(6) . . . 3_666 ?
N9 N8 C3 O3 178.1(6) . . . . ?
N9 N8 C3 N6 -2.4(9) . . . . ?
N7 N6 C3 O3 -6.4(8) . . . . ?
N7 N6 C3 N8 174.0(6) . . . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.077

