# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_5-AtP
_database_code_depnum_ccdc_archive 'CCDC 2157429'
loop_
_audit_author_name
_audit_author_address
'Michael K. Bellas'
;The University of Michigan
United States of America
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT088_5-AtP               
;
PROBLEM: Poor Data / Parameter Ratio ....................       9.25 Note
RESPONSE: The peroxide molecule is disordered over two positions with unequal occupancy.
;
# Added during the CSD deposition process: Wednesday 09 March 2022 02:09 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        5-aminotetrazole-peroxosolvate
_chemical_name_common            5-AtP
_chemical_melting_point          ?
_chemical_formula_moiety         'C H3 N5, H2 O2'
_chemical_formula_sum            'C H5 N5 O2'
_chemical_formula_weight         119.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           53
_space_group_name_H-M_alt        'P m n a'
_space_group_name_Hall           '-P 2ac 2'

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

_cell_length_a                   9.9196(2)
_cell_length_b                   6.44705(16)
_cell_length_c                   8.1105(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     518.68(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2772
_cell_measurement_theta_min      6.8500
_cell_measurement_theta_max      75.7370

_exptl_crystal_description       blade
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.208
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4630
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.868
_diffrn_reflns_theta_max         66.564
_diffrn_reflns_theta_full        66.564
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             490
_reflns_number_gt                450
_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0527P)²+0.0951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         490
_refine_ls_number_parameters     53
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
N1 N 0.39161(11) 0.48838(17) 0.25318(15) 0.0462(4) Uani 1 1 d . . . . .
H1 H 0.308926 0.452098 0.239532 0.055 Uiso 0.5 1 calc R U P . .
N2 N 0.43549(12) 0.66670(18) 0.32105(17) 0.0544(5) Uani 1 1 d . . . . .
N4 N 0.500000 0.1950(3) 0.1376(3) 0.0680(7) Uani 1 2 d S T P . .
H4A H 0.424924 0.136118 0.112706 0.082 Uiso 0.5 1 calc R U P . .
H4B H 0.575076 0.134795 0.114794 0.082 Uiso 0.5 1 calc R U P . .
C3 C 0.500000 0.3788(3) 0.2112(2) 0.0419(5) Uani 1 2 d S T P . .
O7B O 0.2725(3) 1.0137(11) 0.4118(6) 0.0620(14) Uani 0.657(15) 1 d . . P A 2
H7B H 0.318097 0.922428 0.368825 0.093 Uiso 0.657(15) 1 calc R U P A 2
O7A O 0.2727(6) 0.8973(18) 0.5333(16) 0.080(2) Uani 0.343(15) 1 d . . P A 1
H7A H 0.323368 0.823593 0.478971 0.120 Uiso 0.343(15) 1 calc R U P 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
N1 C3 1.3310(16) . ?
N1 N2 1.3469(17) . ?
N1 H1 0.8600 . ?
N2 N2 1.280(2) 8_655 ?
N4 C3 1.326(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
O7B O7B 1.442(8) 4_576 ?
O7B H7B 0.8200 . ?
O7A O7A 1.430(16) 4_576 ?
O7A H7A 0.8200 . ?

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
C3 N1 N2 107.26(11) . . ?
C3 N1 H1 126.4 . . ?
N2 N1 H1 126.4 . . ?
N2 N2 N1 108.86(7) 8_655 . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N4 C3 N1 126.11(8) . . ?
N4 C3 N1 126.11(8) . 8_655 ?
N1 C3 N1 107.77(16) . 8_655 ?
O7B O7B H7B 109.5 4_576 . ?
O7A O7A H7A 109.5 4_576 . ?

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
C3 N1 N2 N2 -0.10(13) . . . 8_655 ?
N2 N1 C3 N4 -178.6(2) . . . . ?
N2 N1 C3 N1 0.2(2) . . . 8_655 ?

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032



####################################################################### 
# 
# 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_DDP
_database_code_depnum_ccdc_archive 'CCDC 2157430'
loop_
_audit_author_name
_audit_author_address
'Michael K. Bellas'
;The University of Michigan
United States of America
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
3,4-diaminofurazan-3,4-dinitro-1H-pyrazole-peroxosolvate
_chemical_name_common            DDP
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H2 N4 O4, C2 H4 N4 O, H2 O2'
_chemical_formula_sum            'C5 H8 N8 O7'
_chemical_formula_weight         292.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   25.6236(2)
_cell_length_b                   5.46400(10)
_cell_length_c                   8.13850(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.7550(10)
_cell_angle_gamma                90
_cell_volume                     1131.54(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11821
_cell_measurement_theta_min      3.4550
_cell_measurement_theta_max      75.8430

_exptl_crystal_description       blade
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.011
_exptl_crystal_size_min          0.006
_exptl_absorpt_coefficient_mu    1.402
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13522
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.474
_diffrn_reflns_theta_max         76.159
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             2224
_reflns_number_gt                2188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_fraction_full    0.890

_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0329P)²+0.2751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2224
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0617
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.082
_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
O19 O 0.52343(5) -0.4785(3) 0.45858(19) 0.0521(4) Uani 1 1 d . . . . .
H19 H 0.546914 -0.404567 0.515157 0.078 Uiso 1 1 calc R U . . .
O11 O 0.35876(6) 1.4736(3) 0.53048(19) 0.0518(4) Uani 1 1 d . . . . .
O20 O 0.49182(6) 0.5471(3) 0.91224(17) 0.0517(4) Uani 1 1 d . . . . .
H20 H 0.5170(13) 0.438(7) 0.883(4) 0.078 Uiso 1 1 d . U . . .
O8 O 0.25273(5) 0.9713(3) 0.7264(2) 0.0523(4) Uani 1 1 d . . . . .
N9 N 0.33588(6) 1.3647(3) 0.63251(19) 0.0357(4) Uani 1 1 d . . . . .
O10 O 0.29416(5) 1.4299(3) 0.6763(2) 0.0512(4) Uani 1 1 d . . . . .
O15 O 0.54111(5) 0.0150(3) 0.7350(2) 0.0536(4) Uani 1 1 d . . . . .
O7 O 0.28161(6) 0.8132(4) 0.9624(2) 0.0590(5) Uani 1 1 d . . . . .
N2 N 0.37818(6) 0.8125(3) 0.86067(18) 0.0349(4) Uani 1 1 d . . . . .
N6 N 0.28793(6) 0.9157(3) 0.83336(19) 0.0367(4) Uani 1 1 d . . . . .
N1 N 0.42183(6) 0.8990(3) 0.80289(19) 0.0361(4) Uani 1 1 d . . . . .
H1 H 0.4506(10) 0.820(5) 0.825(3) 0.043 Uiso 1 1 d . U . . .
N14 N 0.56281(6) 0.2149(3) 0.8249(2) 0.0438(4) Uani 1 1 d . . . . .
N17 N 0.67151(6) -0.0530(4) 0.6645(2) 0.0432(4) Uani 1 1 d . . . . .
H17A H 0.6729(10) -0.198(7) 0.616(3) 0.052 Uiso 1 1 d . U . . .
H17B H 0.6976(11) -0.011(6) 0.724(3) 0.052 Uiso 1 1 d . U . . .
N16 N 0.58069(6) -0.1126(3) 0.6670(2) 0.0446(4) Uani 1 1 d . . . . .
N18 N 0.64827(8) 0.3675(4) 0.8919(2) 0.0454(4) Uani 1 1 d . . . . .
H18A H 0.6355(10) 0.491(6) 0.940(3) 0.055 Uiso 1 1 d . U . . .
H18B H 0.6750(11) 0.389(6) 0.849(3) 0.055 Uiso 1 1 d . U . . .
C4 C 0.36101(6) 1.1526(3) 0.7071(2) 0.0297(4) Uani 1 1 d . . . . .
C13 C 0.61281(7) 0.2111(3) 0.8136(2) 0.0327(4) Uani 1 1 d . . . . .
C3 C 0.34136(6) 0.9683(3) 0.80270(19) 0.0299(4) Uani 1 1 d . . . . .
C5 C 0.41370(7) 1.1005(4) 0.7111(2) 0.0345(4) Uani 1 1 d . . . . .
H5 H 0.4404(9) 1.180(5) 0.666(3) 0.041 Uiso 1 1 d . U . . .
C12 C 0.62397(7) 0.0038(4) 0.7134(2) 0.0330(4) 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
O19 O19 1.444(3) 2_656 ?
O19 H19 0.8200 . ?
O11 N9 1.225(2) . ?
O20 O20 1.441(3) 2_657 ?
O20 H20 0.93(3) . ?
O8 N6 1.216(2) . ?
N9 O10 1.219(2) . ?
N9 C4 1.427(2) . ?
O15 N14 1.393(2) . ?
O15 N16 1.397(2) . ?
O7 N6 1.218(2) . ?
N2 C3 1.316(2) . ?
N2 N1 1.349(2) . ?
N6 C3 1.449(2) . ?
N1 C5 1.333(3) . ?
N1 H1 0.86(3) . ?
N14 C13 1.295(2) . ?
N17 C12 1.361(2) . ?
N17 H17A 0.89(3) . ?
N17 H17B 0.81(3) . ?
N16 C12 1.296(3) . ?
N18 C13 1.351(3) . ?
N18 H18A 0.86(3) . ?
N18 H18B 0.81(3) . ?
C4 C5 1.377(2) . ?
C4 C3 1.402(2) . ?
C13 C12 1.444(3) . ?
C5 H5 0.92(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
O19 O19 H19 109.5 2_656 . ?
O20 O20 H20 97.3(19) 2_657 . ?
O10 N9 O11 124.21(17) . . ?
O10 N9 C4 118.69(16) . . ?
O11 N9 C4 117.07(15) . . ?
N14 O15 N16 109.61(13) . . ?
C3 N2 N1 103.71(15) . . ?
O8 N6 O7 124.72(16) . . ?
O8 N6 C3 117.62(15) . . ?
O7 N6 C3 117.63(15) . . ?
C5 N1 N2 113.80(15) . . ?
C5 N1 H1 127.6(17) . . ?
N2 N1 H1 118.6(17) . . ?
C13 N14 O15 106.71(15) . . ?
C12 N17 H17A 114.7(17) . . ?
C12 N17 H17B 117.7(18) . . ?
H17A N17 H17B 116(3) . . ?
C12 N16 O15 106.00(16) . . ?
C13 N18 H18A 115.8(18) . . ?
C13 N18 H18B 116(2) . . ?
H18A N18 H18B 118(3) . . ?
C5 C4 C3 104.69(15) . . ?
C5 C4 N9 124.78(17) . . ?
C3 C4 N9 130.28(15) . . ?
N14 C13 N18 124.93(18) . . ?
N14 C13 C12 108.39(16) . . ?
N18 C13 C12 126.56(17) . . ?
N2 C3 C4 112.00(15) . . ?
N2 C3 N6 117.51(16) . . ?
C4 C3 N6 130.26(15) . . ?
N1 C5 C4 105.80(16) . . ?
N1 C5 H5 122.6(16) . . ?
C4 C5 H5 131.6(16) . . ?
N16 C12 N17 124.58(19) . . ?
N16 C12 C13 109.28(15) . . ?
N17 C12 C13 125.98(18) . . ?

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
C3 N2 N1 C5 -0.3(2) . . . . ?
N16 O15 N14 C13 -0.1(2) . . . . ?
N14 O15 N16 C12 0.0(2) . . . . ?
O10 N9 C4 C5 -158.66(19) . . . . ?
O11 N9 C4 C5 19.6(3) . . . . ?
O10 N9 C4 C3 14.7(3) . . . . ?
O11 N9 C4 C3 -167.13(18) . . . . ?
O15 N14 C13 N18 -176.08(19) . . . . ?
O15 N14 C13 C12 0.2(2) . . . . ?
N1 N2 C3 C4 0.52(19) . . . . ?
N1 N2 C3 N6 175.56(15) . . . . ?
C5 C4 C3 N2 -0.5(2) . . . . ?
N9 C4 C3 N2 -174.86(17) . . . . ?
C5 C4 C3 N6 -174.77(18) . . . . ?
N9 C4 C3 N6 10.9(3) . . . . ?
O8 N6 C3 N2 -145.01(18) . . . . ?
O7 N6 C3 N2 33.1(3) . . . . ?
O8 N6 C3 C4 29.0(3) . . . . ?
O7 N6 C3 C4 -152.9(2) . . . . ?
N2 N1 C5 C4 0.0(2) . . . . ?
C3 C4 C5 N1 0.30(19) . . . . ?
N9 C4 C5 N1 175.03(16) . . . . ?
O15 N16 C12 N17 -175.71(19) . . . . ?
O15 N16 C12 C13 0.1(2) . . . . ?
N14 C13 C12 N16 -0.2(2) . . . . ?
N18 C13 C12 N16 176.0(2) . . . . ?
N14 C13 C12 N17 175.54(19) . . . . ?
N18 C13 C12 N17 -8.3(3) . . . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_DDH
_database_code_depnum_ccdc_archive 'CCDC 2157431'
loop_
_audit_author_name
_audit_author_address
'Michael K. Bellas'
;The University of Michigan
United States of America
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
3,4-diaminofurazan-3,4-dinitro-1H-pyrazole-hydrate
_chemical_name_common            DDH
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H2 N4 O4, C2 H4 N4 O, H2 O1'
_chemical_formula_sum            'C5 H8 N8 O6'
_chemical_formula_weight         276.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.36177(4)
_cell_length_b                   8.07141(5)
_cell_length_c                   25.18846(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1090.081(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19647
_cell_measurement_theta_min      3.5030
_cell_measurement_theta_max      76.0440

_exptl_crystal_description       blade
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.344
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            26839
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.509
_diffrn_reflns_theta_max         76.310
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2275
_reflns_number_gt                2208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     0.988
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0564P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2275
_refine_ls_number_parameters     181
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
O4 O -0.0083(4) 0.0723(2) 0.28964(6) 0.0497(5) Uani 1 1 d . . . . .
O18 O 1.3900(3) 0.6017(3) 0.45046(7) 0.0507(5) Uani 1 1 d . . . . .
O17 O 1.4331(4) 0.7576(2) 0.38142(8) 0.0538(5) Uani 1 1 d . . . . .
O15 O 0.9293(4) 0.5350(2) 0.49345(6) 0.0522(5) Uani 1 1 d . . . . .
O19 O 0.5462(4) 0.3441(3) 0.24781(7) 0.0532(5) Uani 1 1 d D . . . .
H19A H 0.453(7) 0.372(5) 0.2209(12) 0.080 Uiso 1 1 d D U . . .
H19B H 0.439(7) 0.285(4) 0.2661(14) 0.080 Uiso 1 1 d D U . . .
O14 O 0.7726(4) 0.3012(3) 0.46817(7) 0.0576(6) Uani 1 1 d . . . . .
N9 N 0.7695(4) 0.4205(2) 0.36827(7) 0.0337(4) Uani 1 1 d . . . . .
N10 N 0.8564(3) 0.4861(2) 0.32278(6) 0.0347(4) Uani 1 1 d . . . . .
H10 H 0.787892 0.469160 0.292391 0.042 Uiso 1 1 calc R U . . .
N13 N 0.8737(4) 0.4340(2) 0.45943(7) 0.0361(4) Uani 1 1 d . . . . .
N16 N 1.3242(4) 0.6509(2) 0.40689(7) 0.0355(4) Uani 1 1 d . . . . .
N3 N 0.1941(4) 0.1522(3) 0.31341(7) 0.0399(4) Uani 1 1 d . . . . .
N6 N -0.0920(4) -0.0655(3) 0.41926(7) 0.0415(5) Uani 1 1 d . . . . .
H6A H -0.081431 0.005482 0.444776 0.050 Uiso 1 1 d R U . . .
H6B H -0.243331 -0.101258 0.417336 0.050 Uiso 1 1 d R U . . .
N7 N 0.3380(4) 0.1727(3) 0.40118(8) 0.0429(5) Uani 1 1 d . . . . .
H7A H 0.469065 0.215960 0.386582 0.052 Uiso 1 1 d R U . . .
H7B H 0.262365 0.248316 0.419533 0.052 Uiso 1 1 d R U . . .
N5 N -0.1437(4) -0.0171(3) 0.32735(7) 0.0438(5) Uani 1 1 d . . . . .
C12 C 1.1105(4) 0.5769(2) 0.38285(8) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.1823(4) 0.1139(2) 0.36345(8) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.9252(4) 0.4754(2) 0.40470(7) 0.0293(4) Uani 1 1 d . . . . .
C1 C -0.0293(4) 0.0071(3) 0.37226(8) 0.0318(4) Uani 1 1 d . . . . .
C11 C 1.0582(4) 0.5796(3) 0.32924(8) 0.0338(4) Uani 1 1 d . . . . .
H11 H 1.146259 0.635550 0.302959 0.041 Uiso 1 1 calc R U . . .


_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
O4 N5 1.397(3) . ?
O4 N3 1.397(3) . ?
O18 N16 1.219(3) . ?
O17 N16 1.223(3) . ?
O15 N13 1.220(3) . ?
O19 H19A 0.87(2) . ?
O19 H19B 0.88(2) . ?
O14 N13 1.221(3) . ?
N9 C8 1.318(3) . ?
N9 N10 1.346(2) . ?
N10 C11 1.329(3) . ?
N10 H10 0.8600 . ?
N13 C8 1.445(3) . ?
N16 C12 1.427(3) . ?
N3 C2 1.299(3) . ?
N6 C1 1.363(3) . ?
N6 H6A 0.8629 . ?
N6 H6B 0.8625 . ?
N7 C2 1.351(3) . ?
N7 H7A 0.8665 . ?
N7 H7B 0.8666 . ?
N5 C1 1.301(3) . ?
C12 C11 1.379(3) . ?
C12 C8 1.401(3) . ?
C2 C1 1.442(3) . ?
C11 H11 0.9300 . ?

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
N5 O4 N3 110.52(14) . . ?
H19A O19 H19B 100(3) . . ?
C8 N9 N10 103.95(17) . . ?
C11 N10 N9 113.66(17) . . ?
C11 N10 H10 123.2 . . ?
N9 N10 H10 123.2 . . ?
O15 N13 O14 124.64(19) . . ?
O15 N13 C8 117.97(18) . . ?
O14 N13 C8 117.37(18) . . ?
O18 N16 O17 124.3(2) . . ?
O18 N16 C12 118.58(19) . . ?
O17 N16 C12 117.11(19) . . ?
C2 N3 O4 105.57(18) . . ?
C1 N6 H6A 110.2 . . ?
C1 N6 H6B 109.1 . . ?
H6A N6 H6B 109.0 . . ?
C2 N7 H7A 110.1 . . ?
C2 N7 H7B 109.5 . . ?
H7A N7 H7B 108.8 . . ?
C1 N5 O4 105.59(18) . . ?
C11 C12 C8 104.47(17) . . ?
C11 C12 N16 124.90(19) . . ?
C8 C12 N16 130.36(18) . . ?
N3 C2 N7 124.7(2) . . ?
N3 C2 C1 109.24(18) . . ?
N7 C2 C1 126.01(18) . . ?
N9 C8 C12 111.88(17) . . ?
N9 C8 N13 117.75(18) . . ?
C12 C8 N13 130.22(18) . . ?
N5 C1 N6 125.0(2) . . ?
N5 C1 C2 109.07(19) . . ?
N6 C1 C2 125.78(19) . . ?
N10 C11 C12 106.04(18) . . ?
N10 C11 H11 127.0 . . ?
C12 C11 H11 127.0 . . ?

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
C8 N9 N10 C11 -0.2(2) . . . . ?
N5 O4 N3 C2 -0.3(2) . . . . ?
N3 O4 N5 C1 0.1(3) . . . . ?
O18 N16 C12 C11 -158.8(2) . . . . ?
O17 N16 C12 C11 19.4(3) . . . . ?
O18 N16 C12 C8 14.2(3) . . . . ?
O17 N16 C12 C8 -167.5(2) . . . . ?
O4 N3 C2 N7 -176.6(2) . . . . ?
O4 N3 C2 C1 0.3(2) . . . . ?
N10 N9 C8 C12 0.4(2) . . . . ?
N10 N9 C8 N13 176.42(18) . . . . ?
C11 C12 C8 N9 -0.5(2) . . . . ?
N16 C12 C8 N9 -174.6(2) . . . . ?
C11 C12 C8 N13 -175.8(2) . . . . ?
N16 C12 C8 N13 10.0(4) . . . . ?
O15 N13 C8 N9 -146.4(2) . . . . ?
O14 N13 C8 N9 32.2(3) . . . . ?
O15 N13 C8 C12 28.8(3) . . . . ?
O14 N13 C8 C12 -152.6(2) . . . . ?
O4 N5 C1 N6 -176.2(2) . . . . ?
O4 N5 C1 C2 0.1(3) . . . . ?
N3 C2 C1 N5 -0.3(3) . . . . ?
N7 C2 C1 N5 176.6(2) . . . . ?
N3 C2 C1 N6 176.0(2) . . . . ?
N7 C2 C1 N6 -7.1(3) . . . . ?
N9 N10 C11 C12 -0.1(2) . . . . ?
C8 C12 C11 N10 0.3(2) . . . . ?
N16 C12 C11 N10 174.88(19) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.042



