# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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 2165690'
loop_
_audit_author_name
_audit_author_address
'Ning Ding'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(4-amino-3,5-dinitro-1H-pyrazol-1-yl)propan-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 N5 O5'
_chemical_formula_weight         229.17

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.554(2)
_cell_length_b                   21.006(11)
_cell_length_c                   9.757(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.452(9)
_cell_angle_gamma                90
_cell_volume                     927.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    859
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      18.09

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.972
_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            9600
_diffrn_reflns_av_unetI/netI     0.1330
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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             1619
_reflns_number_gt                830
_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)+(0.0411P)²+2.8513P] 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         1619
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2171
_refine_ls_R_factor_gt           0.1068
_refine_ls_wR_factor_ref         0.1983
_refine_ls_wR_factor_gt          0.1634
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.6304(13) 0.3899(3) 0.6326(6) 0.0335(15) Uani 1 1 d . . . . .
C2 C 0.6570(13) 0.3240(3) 0.6090(6) 0.0313(15) Uani 1 1 d . . . . .
C3 C 0.8420(13) 0.3237(3) 0.5060(6) 0.0320(15) Uani 1 1 d . . . . .
C4 C 1.0487(13) 0.4110(3) 0.3579(6) 0.0342(16) Uani 1 1 d . . . . .
H4A H 1.2419 0.3919 0.3555 0.041 Uiso 1 1 calc R U . . .
H4B H 1.0755 0.4566 0.3693 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8594(15) 0.3978(3) 0.2235(6) 0.0363(16) Uani 1 1 d . . . . .
C6 C 0.9706(16) 0.4266(3) 0.0980(7) 0.054(2) Uani 1 1 d . . . . .
H6A H 1.1305 0.4014 0.0713 0.081 Uiso 1 1 calc R U . . .
H6B H 1.0391 0.4691 0.1189 0.081 Uiso 1 1 calc R U . . .
H6C H 0.8133 0.4278 0.0238 0.081 Uiso 1 1 calc R U . . .
N1 N 0.4629(12) 0.4195(3) 0.7314(6) 0.0452(15) Uani 1 1 d . . . . .
N2 N 0.7791(11) 0.4263(2) 0.5517(5) 0.0348(13) Uani 1 1 d . . . . .
N3 N 0.9113(11) 0.3852(2) 0.4757(5) 0.0349(13) Uani 1 1 d . . . . .
N4 N 0.5291(11) 0.2748(2) 0.6671(5) 0.0431(15) Uani 1 1 d . . . . .
H4C H 0.5590 0.2365 0.6404 0.052 Uiso 1 1 calc R U . . .
H4D H 0.4173 0.2815 0.7310 0.052 Uiso 1 1 calc R U . . .
N5 N 0.9549(12) 0.2701(3) 0.4427(5) 0.0385(14) Uani 1 1 d . . . . .
O1 O 0.3137(11) 0.3836(2) 0.7964(5) 0.0623(15) Uani 1 1 d . . . . .
O2 O 0.4714(11) 0.4774(3) 0.7437(5) 0.0674(16) Uani 1 1 d . . . . .
O3 O 0.6379(10) 0.3667(2) 0.2196(4) 0.0456(13) Uani 1 1 d . . . . .
O4 O 1.1382(10) 0.2779(2) 0.3596(5) 0.0484(13) Uani 1 1 d . . . . .
O5 O 0.8676(11) 0.2175(2) 0.4772(5) 0.0567(14) 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 1.336(7) . ?
C1 C2 1.410(8) . ?
C1 N1 1.436(8) . ?
C2 N4 1.344(7) . ?
C2 C3 1.382(8) . ?
C3 N3 1.370(7) . ?
C3 N5 1.408(7) . ?
C4 N3 1.472(7) . ?
C4 C5 1.512(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O3 1.199(7) . ?
C5 C6 1.504(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N1 O2 1.223(6) . ?
N1 O1 1.236(6) . ?
N2 N3 1.325(6) . ?
N4 H4C 0.8600 . ?
N4 H4D 0.8600 . ?
N5 O5 1.235(6) . ?
N5 O4 1.238(6) . ?

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 C2 114.0(5) . . ?
N2 C1 N1 119.4(5) . . ?
C2 C1 N1 126.6(6) . . ?
N4 C2 C3 129.2(6) . . ?
N4 C2 C1 129.6(6) . . ?
C3 C2 C1 101.2(5) . . ?
N3 C3 C2 109.1(5) . . ?
N3 C3 N5 123.7(5) . . ?
C2 C3 N5 127.2(6) . . ?
N3 C4 C5 111.0(5) . . ?
N3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O3 C5 C6 123.5(6) . . ?
O3 C5 C4 121.6(6) . . ?
C6 C5 C4 114.9(6) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 N1 O1 124.7(6) . . ?
O2 N1 C1 118.9(6) . . ?
O1 N1 C1 116.4(6) . . ?
N3 N2 C1 104.5(4) . . ?
N2 N3 C3 111.2(5) . . ?
N2 N3 C4 117.2(5) . . ?
C3 N3 C4 130.1(5) . . ?
C2 N4 H4C 120.0 . . ?
C2 N4 H4D 120.0 . . ?
H4C N4 H4D 120.0 . . ?
O5 N5 O4 123.9(5) . . ?
O5 N5 C3 116.9(5) . . ?
O4 N5 C3 119.3(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
N2 C1 C2 N4 -177.1(6) . . . . ?
N1 C1 C2 N4 2.6(11) . . . . ?
N2 C1 C2 C3 0.8(7) . . . . ?
N1 C1 C2 C3 -179.5(6) . . . . ?
N4 C2 C3 N3 177.9(6) . . . . ?
C1 C2 C3 N3 0.0(6) . . . . ?
N4 C2 C3 N5 -4.1(11) . . . . ?
C1 C2 C3 N5 178.0(6) . . . . ?
N3 C4 C5 O3 -4.2(8) . . . . ?
N3 C4 C5 C6 175.6(5) . . . . ?
N2 C1 N1 O2 -3.4(9) . . . . ?
C2 C1 N1 O2 177.0(6) . . . . ?
N2 C1 N1 O1 175.1(5) . . . . ?
C2 C1 N1 O1 -4.5(9) . . . . ?
C2 C1 N2 N3 -1.3(7) . . . . ?
N1 C1 N2 N3 179.0(5) . . . . ?
C1 N2 N3 C3 1.3(7) . . . . ?
C1 N2 N3 C4 168.9(5) . . . . ?
C2 C3 N3 N2 -0.8(7) . . . . ?
N5 C3 N3 N2 -178.9(5) . . . . ?
C2 C3 N3 C4 -166.4(6) . . . . ?
N5 C3 N3 C4 15.5(10) . . . . ?
C5 C4 N3 N2 -103.3(6) . . . . ?
C5 C4 N3 C3 61.6(8) . . . . ?
N3 C3 N5 O5 -178.1(5) . . . . ?
C2 C3 N5 O5 4.2(9) . . . . ?
N3 C3 N5 O4 3.6(9) . . . . ?
C2 C3 N5 O4 -174.1(6) . . . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2165694'
loop_
_audit_author_name
_audit_author_address
'Ning Ding'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-dinitromethyl-4-diazo-3-nitro-5-oxo-pyrazole
_chemical_name_common            
2-(dinitromethyl)-5-nitro-3-oxo-pyrazole-4-diazonium
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H N7 O7'
_chemical_formula_weight         259.12

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.5251(5)
_cell_length_b                   13.8205(13)
_cell_length_c                   12.4504(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.952(2)
_cell_angle_gamma                90
_cell_volume                     948.45(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2292
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      21.10

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.966
_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            11103
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.948
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_full        24.984
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1667
_reflns_number_gt                1007
_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)+(0.0536P)²+0.4291P] 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         1667
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.5278(5) 0.3835(2) 0.7273(2) 0.0425(7) Uani 1 1 d . . . A 1
C2 C 0.1699(5) 0.4398(2) 0.6463(2) 0.0409(7) Uani 1 1 d . . . A 1
C3 C 0.2024(5) 0.3255(2) 0.4928(2) 0.0430(8) Uani 1 1 d . . . A 1
H3 H 0.0354 0.3464 0.4739 0.052 Uiso 1 1 calc R U . A 1
N1 N 0.7417(5) 0.3710(2) 0.7994(2) 0.0578(8) Uani 1 1 d . . . A 1
N2 N 0.4947(4) 0.32940(18) 0.64366(19) 0.0475(7) Uani 1 1 d . . . A 1
N3 N 0.2795(4) 0.36332(18) 0.59320(18) 0.0448(7) Uani 1 1 d . . . A 1
N4 N 0.2106(6) 0.2159(2) 0.4986(2) 0.0558(8) Uani 1 1 d . . . A 1
N5 N 0.3622(6) 0.35526(19) 0.4040(2) 0.0549(7) Uani 1 1 d . . . A 1
C4 C 0.3450(5) 0.4528(2) 0.7360(2) 0.0422(8) Uani 1 1 d . . . A 1
N6 N 0.3317(5) 0.5222(2) 0.8097(2) 0.0564(7) Uani 1 1 d . . . A 1
N7 N 0.3197(6) 0.5805(3) 0.8700(3) 0.0909(12) Uani 1 1 d . . . A 1
O1 O 0.8606(5) 0.2985(2) 0.7932(2) 0.0893(9) Uani 1 1 d . . . A 1
O2 O 0.7857(4) 0.4376(2) 0.86209(19) 0.0748(8) Uani 1 1 d . . . A 1
O3 O -0.0200(4) 0.47803(16) 0.61817(16) 0.0541(6) Uani 1 1 d . . . A 1
O4 O 0.0758(6) 0.1808(2) 0.5588(2) 0.1043(11) Uani 1 1 d . . . A 1
O5 O 0.3495(5) 0.17296(17) 0.4468(2) 0.0708(7) Uani 1 1 d . . . A 1
O6 O 0.5570(5) 0.3906(2) 0.4301(2) 0.0882(9) Uani 1 1 d . . . A 1
O7 O 0.2807(5) 0.34114(18) 0.31370(19) 0.0756(8) Uani 1 1 d . . . A 1


_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 1.285(4) . ?
C1 C4 1.402(4) . ?
C1 N1 1.444(4) . ?
C2 O3 1.205(3) . ?
C2 N3 1.406(4) . ?
C2 C4 1.438(4) . ?
C3 N3 1.394(3) . ?
C3 N4 1.516(4) . ?
C3 N5 1.518(4) . ?
C3 H3 0.9800 . ?
N1 O1 1.203(4) . ?
N1 O2 1.221(3) . ?
N2 N3 1.387(3) . ?
N4 O4 1.195(3) . ?
N4 O5 1.194(3) . ?
N5 O7 1.198(3) . ?
N5 O6 1.206(3) . ?
C4 N6 1.333(4) . ?
N6 N7 1.106(4) . ?

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 C4 113.4(2) . . ?
N2 C1 N1 119.9(3) . . ?
C4 C1 N1 126.7(3) . . ?
O3 C2 N3 126.0(3) . . ?
O3 C2 C4 134.2(3) . . ?
N3 C2 C4 99.8(2) . . ?
N3 C3 N4 109.0(2) . . ?
N3 C3 N5 113.2(2) . . ?
N4 C3 N5 106.8(2) . . ?
N3 C3 H3 109.3 . . ?
N4 C3 H3 109.3 . . ?
N5 C3 H3 109.3 . . ?
O1 N1 O2 125.7(3) . . ?
O1 N1 C1 119.1(3) . . ?
O2 N1 C1 115.2(3) . . ?
C1 N2 N3 103.9(2) . . ?
N2 N3 C3 118.6(2) . . ?
N2 N3 C2 115.1(2) . . ?
C3 N3 C2 126.1(2) . . ?
O4 N4 O5 126.0(3) . . ?
O4 N4 C3 114.7(3) . . ?
O5 N4 C3 119.3(3) . . ?
O7 N5 O6 126.1(3) . . ?
O7 N5 C3 116.1(3) . . ?
O6 N5 C3 117.8(3) . . ?
N6 C4 C1 128.3(3) . . ?
N6 C4 C2 124.0(3) . . ?
C1 C4 C2 107.7(2) . . ?
N7 N6 C4 179.2(4) . . ?

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
N2 C1 N1 O1 -14.9(4) . . . . ?
C4 C1 N1 O1 167.0(3) . . . . ?
N2 C1 N1 O2 164.6(3) . . . . ?
C4 C1 N1 O2 -13.5(4) . . . . ?
C4 C1 N2 N3 -0.1(3) . . . . ?
N1 C1 N2 N3 -178.3(2) . . . . ?
C1 N2 N3 C3 174.0(2) . . . . ?
C1 N2 N3 C2 -1.0(3) . . . . ?
N4 C3 N3 N2 49.7(3) . . . . ?
N5 C3 N3 N2 -68.9(3) . . . . ?
N4 C3 N3 C2 -135.9(3) . . . . ?
N5 C3 N3 C2 105.4(3) . . . . ?
O3 C2 N3 N2 -177.8(3) . . . . ?
C4 C2 N3 N2 1.5(3) . . . . ?
O3 C2 N3 C3 7.7(5) . . . . ?
C4 C2 N3 C3 -173.0(3) . . . . ?
N3 C3 N4 O4 63.7(3) . . . . ?
N5 C3 N4 O4 -173.7(3) . . . . ?
N3 C3 N4 O5 -114.6(3) . . . . ?
N5 C3 N4 O5 8.0(3) . . . . ?
N3 C3 N5 O7 -166.0(3) . . . . ?
N4 C3 N5 O7 74.0(3) . . . . ?
N3 C3 N5 O6 13.9(4) . . . . ?
N4 C3 N5 O6 -106.1(3) . . . . ?
N2 C1 C4 N6 -176.5(3) . . . . ?
N1 C1 C4 N6 1.6(5) . . . . ?
N2 C1 C4 C2 1.0(3) . . . . ?
N1 C1 C4 C2 179.1(3) . . . . ?
O3 C2 C4 N6 -4.6(5) . . . . ?
N3 C2 C4 N6 176.3(3) . . . . ?
O3 C2 C4 C1 177.8(3) . . . . ?
N3 C2 C4 C1 -1.4(3) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2165695'
loop_
_audit_author_name
_audit_author_address
'Ning Ding'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-trinitromethyl-4-diazo-3-nitro-5-oxo-pyrazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 N8 O9'
_chemical_formula_weight         304.12

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.250(3)
_cell_length_b                   10.283(3)
_cell_length_c                   11.223(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.014(5)
_cell_angle_gamma                90
_cell_volume                     1053.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3875
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      20.85

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.963
_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            21408
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1842
_reflns_number_gt                1130
_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)+(0.0547P)²+0.2935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1842
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.7080(3) 0.6576(2) 0.4197(3) 0.0448(7) Uani 1 1 d . . . . .
C2 C 0.6688(3) 0.4184(2) 0.3823(3) 0.0425(7) Uani 1 1 d . . . . .
C3 C 0.8228(3) 0.6270(3) 0.6462(2) 0.0440(7) Uani 1 1 d . . . . .
N2 N 0.5294(3) 0.4494(2) 0.2500(3) 0.0535(6) Uani 1 1 d . . . . .
N1 N 0.7834(3) 0.3650(3) 0.3423(2) 0.0576(7) Uani 1 1 d . . . . .
N3 N 0.6301(3) 0.3087(2) 0.4562(2) 0.0555(6) Uani 1 1 d . . . . .
N4 N 0.7131(2) 0.52739(19) 0.4627(2) 0.0435(6) Uani 1 1 d . . . . .
N5 N 0.7857(2) 0.5106(2) 0.6006(2) 0.0457(6) Uani 1 1 d . . . . .
C4 C 0.7826(3) 0.7218(3) 0.5464(3) 0.0445(7) Uani 1 1 d . . . . .
N7 N 0.7943(3) 0.8506(3) 0.5627(2) 0.0572(7) Uani 1 1 d . . . . .
N8 N 0.8025(4) 0.9570(3) 0.5747(3) 0.0892(10) Uani 1 1 d . . . . .
N9 N 0.9002(3) 0.6505(3) 0.7886(2) 0.0618(7) Uani 1 1 d . . . . .
O1 O 0.4300(2) 0.4964(2) 0.2636(2) 0.0738(7) Uani 1 1 d . . . . .
O2 O 0.5341(3) 0.4248(3) 0.1485(2) 0.0908(8) Uani 1 1 d . . . . .
O3 O 0.8847(3) 0.4362(2) 0.3656(3) 0.0863(8) Uani 1 1 d . . . . .
O4 O 0.7612(3) 0.2606(2) 0.2903(3) 0.0922(8) Uani 1 1 d . . . . .
O5 O 0.7170(4) 0.2237(3) 0.5007(3) 0.1092(10) Uani 1 1 d . . . . .
O6 O 0.5207(3) 0.3239(2) 0.4665(2) 0.0801(7) Uani 1 1 d . . . . .
O7 O 0.6537(2) 0.69323(18) 0.30507(19) 0.0640(6) Uani 1 1 d . . . . .
O8 O 0.9473(3) 0.7606(3) 0.8202(2) 0.0873(8) Uani 1 1 d . . . . .
O9 O 0.9101(3) 0.5630(3) 0.8639(2) 0.0916(8) 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 O7 1.203(3) . ?
C1 N4 1.416(3) . ?
C1 C4 1.434(4) . ?
C2 N4 1.380(3) . ?
C2 N1 1.537(3) . ?
C2 N3 1.554(3) . ?
C2 N2 1.556(3) . ?
C3 N5 1.289(3) . ?
C3 C4 1.398(4) . ?
C3 N9 1.446(3) . ?
N2 O2 1.189(3) . ?
N2 O1 1.199(3) . ?
N1 O4 1.193(3) . ?
N1 O3 1.199(3) . ?
N3 O5 1.184(3) . ?
N3 O6 1.188(3) . ?
N4 N5 1.390(3) . ?
C4 N7 1.335(4) . ?
N7 N8 1.101(3) . ?
N9 O9 1.206(3) . ?
N9 O8 1.219(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 C1 N4 125.4(2) . . ?
O7 C1 C4 134.4(2) . . ?
N4 C1 C4 100.2(2) . . ?
N4 C2 N1 114.4(2) . . ?
N4 C2 N3 109.2(2) . . ?
N1 C2 N3 108.1(2) . . ?
N4 C2 N2 110.1(2) . . ?
N1 C2 N2 106.6(2) . . ?
N3 C2 N2 108.2(2) . . ?
N5 C3 C4 113.7(2) . . ?
N5 C3 N9 120.6(3) . . ?
C4 C3 N9 125.7(3) . . ?
O2 N2 O1 128.0(3) . . ?
O2 N2 C2 116.8(2) . . ?
O1 N2 C2 115.2(2) . . ?
O4 N1 O3 127.6(3) . . ?
O4 N1 C2 117.6(3) . . ?
O3 N1 C2 114.8(3) . . ?
O5 N3 O6 128.2(3) . . ?
O5 N3 C2 115.8(3) . . ?
O6 N3 C2 115.9(2) . . ?
C2 N4 N5 118.5(2) . . ?
C2 N4 C1 126.5(2) . . ?
N5 N4 C1 114.5(2) . . ?
C3 N5 N4 103.8(2) . . ?
N7 C4 C3 127.3(2) . . ?
N7 C4 C1 124.6(2) . . ?
C3 C4 C1 107.7(2) . . ?
N8 N7 C4 179.1(3) . . ?
O9 N9 O8 126.4(3) . . ?
O9 N9 C3 118.7(3) . . ?
O8 N9 C3 115.0(3) . . ?

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
N4 C2 N2 O2 126.5(3) . . . . ?
N1 C2 N2 O2 1.9(3) . . . . ?
N3 C2 N2 O2 -114.2(3) . . . . ?
N4 C2 N2 O1 -53.0(3) . . . . ?
N1 C2 N2 O1 -177.6(2) . . . . ?
N3 C2 N2 O1 66.3(3) . . . . ?
N4 C2 N1 O4 168.9(2) . . . . ?
N3 C2 N1 O4 47.0(3) . . . . ?
N2 C2 N1 O4 -69.1(3) . . . . ?
N4 C2 N1 O3 -12.4(3) . . . . ?
N3 C2 N1 O3 -134.3(3) . . . . ?
N2 C2 N1 O3 109.6(3) . . . . ?
N4 C2 N3 O5 -105.0(3) . . . . ?
N1 C2 N3 O5 20.0(3) . . . . ?
N2 C2 N3 O5 135.2(3) . . . . ?
N4 C2 N3 O6 71.5(3) . . . . ?
N1 C2 N3 O6 -163.4(2) . . . . ?
N2 C2 N3 O6 -48.3(3) . . . . ?
N1 C2 N4 N5 -89.3(3) . . . . ?
N3 C2 N4 N5 32.0(3) . . . . ?
N2 C2 N4 N5 150.6(2) . . . . ?
N1 C2 N4 C1 82.7(3) . . . . ?
N3 C2 N4 C1 -156.0(2) . . . . ?
N2 C2 N4 C1 -37.3(3) . . . . ?
O7 C1 N4 C2 5.9(4) . . . . ?
C4 C1 N4 C2 -173.7(2) . . . . ?
O7 C1 N4 N5 178.2(3) . . . . ?
C4 C1 N4 N5 -1.3(3) . . . . ?
C4 C3 N5 N4 -1.6(3) . . . . ?
N9 C3 N5 N4 179.1(2) . . . . ?
C2 N4 N5 C3 174.8(2) . . . . ?
C1 N4 N5 C3 1.9(3) . . . . ?
N5 C3 C4 N7 173.5(2) . . . . ?
N9 C3 C4 N7 -7.2(4) . . . . ?
N5 C3 C4 C1 0.8(3) . . . . ?
N9 C3 C4 C1 -179.9(2) . . . . ?
O7 C1 C4 N7 7.9(5) . . . . ?
N4 C1 C4 N7 -172.6(2) . . . . ?
O7 C1 C4 C3 -179.1(3) . . . . ?
N4 C1 C4 C3 0.3(3) . . . . ?
N5 C3 N9 O9 -10.9(4) . . . . ?
C4 C3 N9 O9 169.8(3) . . . . ?
N5 C3 N9 O8 170.4(2) . . . . ?
C4 C3 N9 O8 -8.9(4) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048



