# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_hrf-1-31atry2_auto
_database_code_depnum_ccdc_archive 'CCDC 2483543'
loop_
_audit_author_name
_audit_author_address
'Leila Foroughi'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-12 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'urea hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        'urea hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'C H4 N2 O, H4 N O, N O3'
_chemical_formula_sum            'C H8 N4 O5'
_chemical_formula_weight         156.11
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.71414(12)
_cell_length_b                   9.2773(3)
_cell_length_c                   9.4655(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.516(3)
_cell_angle_gamma                90
_cell_volume                     324.644(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1562
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7270
_cell_measurement_theta_min      4.6970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Isopropanol'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1957
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.755
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.963
_diffrn_reflns_theta_min         4.693
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    127.00 171.00   0.50    0.65    --  110.49  53.00  59.00   88
  2  ω     53.00  78.00   0.50    0.13    --   48.03  53.00  59.00   50
  3  ω      9.00  35.00   0.50    0.13    --   48.03 -53.00 -85.00   52
  4  ω     41.00  69.00   0.50    0.65    --  110.49 -61.00-180.00   56
  5  ω     39.00  91.00   0.50    0.65    --  110.49 -77.00   0.00  104
  6  ω     49.00  74.00   0.50    0.65    --  110.49 -77.00  60.00   50
  7  ω     39.00  66.00   0.50    0.65    --  110.49 -61.00  90.00   54
  8  ω     44.00  70.00   0.50    0.65    --  110.49 -61.00 150.00   52
  9  ω     39.00  68.00   0.50    0.65    --  110.49 -61.00 120.00   58
 10  ω     55.00  91.00   0.50    0.13    --   48.03-125.00 -60.00   72
 11  ω     13.00  51.00   0.50    0.13    --   48.03-125.00 -60.00   76
 12  ω     45.00 101.00   0.50    0.65    --  110.49 -94.00 -60.00  112
 13  ω    -43.00 -17.00   0.50    0.13    --  -48.03  53.00  59.00   52
 14  ω    -40.00  -8.00   0.50    0.13    --  -48.03  37.00 120.00   64
 15  ω     -3.00  23.00   0.50    0.13    --  -48.03  37.00 120.00   52
 16  ω    -60.00 -35.00   0.50    0.65    -- -106.00  61.00   0.00   50
 17  ω    -60.00 -35.00   0.50    0.65    -- -106.00  53.00  59.00   50
 18  ω    -63.00 -38.00   0.50    0.65    -- -106.00  61.00  90.00   50
 19  ω    -80.00 -41.00   0.50    0.13    --  -48.03 -53.00 -85.00   78
 20  ω   -138.00 -88.00   0.50    0.65    -- -106.00 -77.00 -90.00  100
 21  ω   -118.00 -92.00   0.50    0.65    -- -106.00 -53.00 -85.00   52
 22  ω   -175.00-145.00   0.50    0.65    -- -106.00 -77.00 -90.00   60
 23  ω   -176.00-134.00   0.50    0.65    -- -106.00 -15.00 150.00   84
 24  ω   -129.00 -98.00   0.50    0.65    -- -106.00 -15.00 150.00   62
 25  ω   -115.00 -89.00   0.50    0.13    --  -48.03-125.00  90.00   52
 26  ω   -116.00 -78.00   0.50    0.13    --  -48.03-125.00 -90.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.469
_reflns_Friedel_fraction_full    0.572
_reflns_Friedel_fraction_max     0.515
_reflns_number_gt                1019
_reflns_number_total             1040
_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       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
'olex2.solve 1.5-ac5-024 (Bourhis et al., 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_extinction_coef       0.058(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1040
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0812
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N6(H6A,H6B)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N3(H3A,H3B)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.3435(5) 0.39857(18) 0.68040(15) 0.0464(4) Uani 1 1 d . . . . .
O5 O 0.5537(4) 0.6399(2) 0.5670(2) 0.0528(5) Uani 1 1 d . . . . .
H5 H 0.480051 0.562084 0.593547 0.079 Uiso 1 1 calc R U . . .
O7 O 0.0206(8) 0.3197(2) 0.1762(2) 0.0682(6) Uani 1 1 d . . . . .
O10 O 0.0166(6) 0.4380(2) 0.37068(18) 0.0574(5) Uani 1 1 d . . . . .
N8 N 0.0850(5) 0.4304(2) 0.24501(19) 0.0397(4) Uani 1 1 d . . . . .
O9 O 0.2142(7) 0.5361(2) 0.1898(2) 0.0654(6) Uani 1 1 d . . . . .
N6 N 0.2802(4) 0.7078(2) 0.47961(19) 0.0393(5) Uani 1 1 d . . . . .
H6A H 0.144583 0.643759 0.435282 0.047 Uiso 1 1 d R U . . .
H6B H 0.150952 0.760599 0.529992 0.047 Uiso 1 1 d R U . . .
N4 N 0.3554(6) 0.2898(3) 0.8940(2) 0.0515(5) Uani 1 1 d . . . . .
H4A H 0.423132 0.209767 0.859026 0.062 Uiso 1 1 calc R U . . .
H4B H 0.324043 0.295447 0.982626 0.062 Uiso 1 1 calc R U . . .
C2 C 0.2994(5) 0.4039(2) 0.8114(2) 0.0360(4) Uani 1 1 d . . . . .
N3 N 0.1918(7) 0.5237(3) 0.8704(2) 0.0585(7) Uani 1 1 d . . . . .
H3A H 0.150400 0.599904 0.819712 0.070 Uiso 1 1 calc R U . . .
H3B H 0.163288 0.525382 0.959498 0.070 Uiso 1 1 calc R U . . .
H6C H 0.399(7) 0.769(3) 0.420(3) 0.036(6) Uiso 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 C2 1.267(2) . ?
O5 H5 0.8200 . ?
O5 N6 1.397(3) . ?
O7 N8 1.228(3) . ?
O10 N8 1.242(3) . ?
N8 O9 1.230(3) . ?
N6 H6A 0.8614 . ?
N6 H6B 0.8615 . ?
N6 H6C 0.94(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.321(3) . ?
C2 N3 1.323(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

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
N6 O5 H5 109.5 . . ?
O7 N8 O10 120.5(2) . . ?
O7 N8 O9 120.39(19) . . ?
O9 N8 O10 119.08(19) . . ?
O5 N6 H6A 109.6 . . ?
O5 N6 H6B 109.9 . . ?
O5 N6 H6C 105.7(15) . . ?
H6A N6 H6B 109.3 . . ?
H6A N6 H6C 114.3 . . ?
H6B N6 H6C 107.9 . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
O1 C2 N4 121.3(2) . . ?
O1 C2 N3 121.3(2) . . ?
N4 C2 N3 117.4(2) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_ajb-ii-74aredo_auto
_database_code_depnum_ccdc_archive 'CCDC 2483551'
loop_
_audit_author_name
_audit_author_address
'Leila Foroughi'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-12 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-12
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'ANTA hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'3-amino-5-nitro-1h-1,2,4-triazole hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'C2 H3 N5 O2, N O3, H4 N O'
_chemical_formula_sum            'C2 H7 N7 O6'
_chemical_formula_weight         225.15
_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 0.0181 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.1073(3)
_cell_length_b                   8.0654(2)
_cell_length_c                   7.00820(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.474(2)
_cell_angle_gamma                90
_cell_volume                     844.60(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2844
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0800
_cell_measurement_theta_min      2.9620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Isopropanol'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4881
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         2.957
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  70.00   0.50    1.05    --   46.53 -94.00   8.00  130
  2  ω    -51.00 -26.00   0.50    1.05    --  -47.78  94.00 120.00   50
  3  ω    106.00 131.00   0.50    6.32    --  104.41  94.00 120.00   50
  4  ω     66.00  92.00   0.50    6.32    --  104.41 -94.00   8.00   52
  5  ω    -97.00 -58.00   0.50    6.32    -- -105.66  94.00 120.00   78
  6  ω   -142.00-100.00   0.50    6.32    -- -105.66 -94.00   8.00   84
  7  ω    -28.00   4.00   0.50    1.05    --   46.53 -19.00 120.00   64
  8  ω     47.00  80.00   0.50    1.05    --   46.53  57.00 120.00   66
  9  ω     83.00 116.00   0.50    1.05    --   46.53  57.00 120.00   66
 10  ω    -42.00 -16.00   0.50    1.05    --  -47.78  37.00 150.00   52
 11  ω     -8.00  17.00   0.50    1.05    --  -47.78  37.00 150.00   50
 12  ω    -41.00  25.00   0.50    1.05    --  -47.78  37.00  90.00  132
 13  ω     36.00  68.00   0.50    6.32    --  104.41-125.00 -30.00   64
 14  ω     32.00  63.00   0.50    6.32    --  104.41 -61.00 150.00   62
 15  ω     32.00  62.00   0.50    6.32    --  104.41 -61.00  30.00   60
 16  ω    -65.00 -40.00   0.50    6.32    -- -105.66  61.00 -90.00   50
 17  ω    -68.00 -40.00   0.50    6.32    -- -105.66  61.00 -30.00   56
 18  ω    -70.00 -35.00   0.50    6.32    -- -105.66  61.00-120.00   70
 19  ω   -100.00 -43.00   0.50    6.32    -- -105.66  77.00 120.00  114
 20  ω    -86.00 -39.00   0.50    6.32    -- -105.66  77.00-120.00   94
 21  ω    -62.00 -37.00   0.50    6.32    -- -105.66 125.00 -60.00   50
 22  ω   -100.00 -43.00   0.50    6.32    -- -105.66  77.00  60.00  114
 23  ω   -172.00 -83.00   0.50    6.32    -- -105.66 -94.00  30.00  178
 24  ω    -71.00 -45.00   0.50    6.32    -- -105.66  61.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1326
_reflns_number_total             1495
_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       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1495
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.1758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0837
_refine_special_details          
;
ALERT: PLAT430_ALERT_2_B Short Inter D...A Contact  O002     ..O002     .       2.73 Ang.  Check
Response: We have confirmed the atom idenities and there are no missing hydrogens that could participate in a hydrogen bond. The participating atoms are the oxygen atoms on a nitro group.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O00B-N00C \\sim O00C-N1
 with sigma of 0.02
3. Others
 Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(O00C)=Sof(H00G)=1-FVAR(1)
 Sof(O00B)=Sof(H00C)=Sof(N00C)=Sof(H00D)=Sof(H00E)=Sof(H00F)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N009(H009)
4.b X=CH2 refined with riding coordinates:
 N00D(H00A,H00B)
4.c Idealised Me refined as rotating group:
 N00C(H00D,H00E,H00F), N1(H1A,H1B,H1C)
4.d Idealised tetrahedral OH refined as rotating group:
 O00B(H00C), O00C(H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 0.79805(7) 0.97602(14) 0.65931(17) 0.0418(3) Uani 1 1 d . . . . .
O002 O 0.92963(8) 0.94141(14) 0.58166(19) 0.0465(3) Uani 1 1 d . . . . .
O003 O 0.55279(8) 0.19805(16) 0.88108(19) 0.0490(3) Uani 1 1 d . . . . .
N004 N 0.90959(8) 0.60908(14) 0.57128(16) 0.0296(3) Uani 1 1 d . . . . .
O005 O 0.60357(9) 0.44468(15) 0.84499(18) 0.0528(3) Uani 1 1 d . . . . .
O006 O 0.67792(8) 0.23012(15) 0.7753(2) 0.0502(3) Uani 1 1 d . . . . .
N007 N 0.85981(8) 0.88850(15) 0.62469(16) 0.0298(3) Uani 1 1 d . . . . .
N008 N 0.78096(8) 0.64570(15) 0.69743(17) 0.0304(3) Uani 1 1 d . . . . .
N009 N 0.79798(8) 0.48088(15) 0.67639(18) 0.0321(3) Uani 1 1 d . . . . .
H009 H 0.764884 0.401437 0.707369 0.039 Uiso 1 1 calc R U . . .
N00A N 0.61210(8) 0.29341(16) 0.83368(18) 0.0347(3) Uani 1 1 d . . . . .
O00B O 0.60932(10) -0.11755(18) 0.89514(18) 0.0465(5) Uani 0.894(5) 1 d D . P A
1
H00C H 0.590253 -0.023450 0.906685 0.070 Uiso 0.894(5) 1 calc R U P A 1
N00C N 0.61602(14) -0.1475(3) 0.7021(2) 0.0366(5) Uani 0.894(5) 1 d D . P A 1
H00D H 0.564344 -0.187733 0.642701 0.044 Uiso 0.894(5) 1 calc R U P A 1
H00E H 0.659428 -0.220732 0.694453 0.044 Uiso 0.894(5) 1 calc R U P A 1
H00F H 0.628556 -0.053225 0.645770 0.044 Uiso 0.894(5) 1 calc R U P A 1
N00D N 0.90750(10) 0.31540(16) 0.5540(2) 0.0440(4) Uani 1 1 d . . . . .
H00A H 0.955463 0.312286 0.501500 0.053 Uiso 1 1 calc R U . . .
H00B H 0.880983 0.224761 0.576898 0.053 Uiso 1 1 calc R U . . .
C00E C 0.84978(9) 0.71051(16) 0.63220(18) 0.0258(3) Uani 1 1 d . . . . .
C00F C 0.87428(9) 0.46066(17) 0.5999(2) 0.0292(3) Uani 1 1 d . . . . .
N1 N 0.6405(9) -0.2062(17) 0.8456(17) 0.033(4) Uiso 0.106(5) 1 d D . P A 2
H1A H 0.670411 -0.285538 0.793960 0.040 Uiso 0.106(5) 1 calc R U P A 2
H1B H 0.599181 -0.251930 0.907148 0.040 Uiso 0.106(5) 1 calc R U P A 2
H1C H 0.678394 -0.147411 0.928585 0.040 Uiso 0.106(5) 1 calc R U P A 2
O00C O 0.600(2) -0.104(4) 0.702(4) 0.103(12) Uiso 0.106(5) 1 d D . P A 2
H00G H 0.581264 -0.020159 0.749941 0.155 Uiso 0.106(5) 1 calc R U P A 2


_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
O001 N007 1.2225(16) . ?
O002 N007 1.2163(16) . ?
O003 N00A 1.2619(17) . ?
N004 C00E 1.3348(18) . ?
N004 C00F 1.3376(18) . ?
O005 N00A 1.2306(17) . ?
O006 N00A 1.2395(17) . ?
N007 C00E 1.4454(18) . ?
N008 N009 1.3661(17) . ?
N008 C00E 1.3051(18) . ?
N009 H009 0.8600 . ?
N009 C00F 1.3509(19) . ?
O00B H00C 0.8200 . ?
O00B N00C 1.393(2) . ?
N00C H00D 0.8900 . ?
N00C H00E 0.8900 . ?
N00C H00F 0.8900 . ?
N00D H00A 0.8600 . ?
N00D H00B 0.8600 . ?
N00D C00F 1.3325(19) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 O00C 1.378(18) . ?
O00C H00G 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
C00E N004 C00F 101.35(11) . . ?
O001 N007 C00E 118.62(12) . . ?
O002 N007 O001 124.18(13) . . ?
O002 N007 C00E 117.19(12) . . ?
C00E N008 N009 100.35(11) . . ?
N008 N009 H009 124.9 . . ?
C00F N009 N008 110.21(11) . . ?
C00F N009 H009 124.9 . . ?
O005 N00A O003 120.14(13) . . ?
O005 N00A O006 121.75(14) . . ?
O006 N00A O003 118.11(13) . . ?
N00C O00B H00C 109.5 . . ?
O00B N00C H00D 109.5 . . ?
O00B N00C H00E 109.5 . . ?
O00B N00C H00F 109.5 . . ?
H00D N00C H00E 109.5 . . ?
H00D N00C H00F 109.5 . . ?
H00E N00C H00F 109.5 . . ?
H00A N00D H00B 120.0 . . ?
C00F N00D H00A 120.0 . . ?
C00F N00D H00B 120.0 . . ?
N004 C00E N007 121.17(12) . . ?
N008 C00E N004 118.58(12) . . ?
N008 C00E N007 120.25(12) . . ?
N004 C00F N009 109.51(12) . . ?
N00D C00F N004 125.31(13) . . ?
N00D C00F N009 125.15(13) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O00C N1 H1A 109.5 . . ?
O00C N1 H1B 109.5 . . ?
O00C N1 H1C 109.5 . . ?
N1 O00C H00G 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_ajb-ii-231bhan5-atslurry_auto
_database_code_depnum_ccdc_archive 'CCDC 2483549'
loop_
_audit_author_name
_audit_author_address
'Leila Foroughi'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-12 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-12
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'5-aminotetrazole hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'5-aminotetrazole hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'C H3 N5, N O3, H4 N O'
_chemical_formula_sum            'C H7 N7 O4'
_chemical_formula_weight         181.14
_chemical_absolute_configuration ?
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.5879(5)
_cell_length_b                   3.67189(9)
_cell_length_c                   10.8826(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     702.81(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9250
_cell_measurement_theta_min      2.6660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Isopropanol'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2548
_diffrn_reflns_point_group_measured_fraction_full 0.709
_diffrn_reflns_point_group_measured_fraction_max 0.677
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.270
_diffrn_reflns_theta_min         5.029
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  27.00   0.50    0.23    --   47.78 -89.00-130.00   80
  2  ω    -71.00 -37.00   0.50    1.01    -- -106.00  61.00-180.00   68
  3  ω    -65.00 -39.00   0.50    1.01    -- -106.00  61.00-150.00   52
  4  ω    -28.00  27.00   0.50    0.23    --  -47.78  19.00   0.00  110
  5  ω    -69.00 -37.00   0.50    1.01    -- -106.00  61.00  90.00   64
  6  ω    -66.00 -37.00   0.50    1.01    -- -106.00  61.00  60.00   58
  7  ω   -123.00 -79.00   0.50    1.01    -- -106.00 -89.00-130.00   88
  8  ω   -148.00 -86.00   0.50    1.01    -- -106.00-100.00 -26.00  124
  9  ω   -162.00-137.00   0.50    1.01    -- -106.00 -89.00-130.00   50
 10  ω    -84.00 -41.00   0.50    1.01    -- -106.00  89.00 -15.00   86
 11  ω    -27.00  30.00   0.50    0.23    --   47.78 -19.00 -30.00  114
 12  ω    -23.00   2.00   0.50    0.23    --   47.78 -19.00-120.00   50
 13  ω     -8.00  24.00   0.50    0.23    --   47.78 -41.00  71.00   64
 14  ω     59.00  84.00   0.50    1.01    --  109.86 -77.00 -60.00   50
 15  ω     40.00  67.00   0.50    1.01    --  109.86 -61.00 -90.00   54
 16  ω    114.00 139.00   0.50    1.01    --  109.86  41.00-136.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.330
_reflns_Friedel_fraction_full    0.382
_reflns_Friedel_fraction_max     0.355
_reflns_number_gt                964
_reflns_number_total             1003
_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       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(3)
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1003
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.0096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0836
_refine_special_details          
'1 outlying reflection was omitted where the |Error/esd| is greater than 10.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N12(H12A,H12B)
2.b X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
2.c Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
N5 N 0.87707(10) 0.2689(5) 0.72188(19) 0.0309(5) Uani 1 1 d . . . . .
N4 N 0.87776(9) 0.2268(5) 0.8459(2) 0.0335(5) Uani 1 1 d . . . . .
O7 O 1.04026(9) 0.4139(6) 0.7869(2) 0.0487(5) Uani 1 1 d . . . . .
N8 N 1.10345(10) 0.5518(5) 0.77250(17) 0.0331(4) Uani 1 1 d . . . . .
N2 N 0.77487(10) 0.4883(5) 0.8016(2) 0.0318(4) Uani 1 1 d . . . . .
O11 O 1.02369(11) 0.0757(4) 1.06960(19) 0.0422(5) Uani 1 1 d . . . . .
H11 H 1.055253 -0.025617 1.113265 0.063 Uiso 1 1 calc R U . . .
O10 O 1.13569(9) 0.7057(6) 0.86202(19) 0.0432(5) Uani 1 1 d . . . . .
O9 O 1.13506(11) 0.5434(7) 0.6705(2) 0.0549(6) Uani 1 1 d . . . . .
C1 C 0.81179(11) 0.4350(5) 0.6961(2) 0.0272(5) Uani 1 1 d . . . . .
N12 N 0.98058(12) -0.1874(5) 1.0074(2) 0.0355(5) Uani 1 1 d . . . . .
H12A H 0.953093 -0.311015 1.058891 0.043 Uiso 1 1 d R U . . .
H12B H 0.950482 -0.083233 0.954742 0.043 Uiso 1 1 d R U . . .
N3 N 0.81702(11) 0.3555(6) 0.89479(18) 0.0356(5) Uani 1 1 d . . . . .
N6 N 0.78701(12) 0.5359(7) 0.5857(2) 0.0437(5) Uani 1 1 d . . . . .
H6A H 0.814300 0.494485 0.521654 0.052 Uiso 1 1 calc R U . . .
H6B H 0.743698 0.642409 0.578440 0.052 Uiso 1 1 calc R U . . .
H12C H 1.012(2) -0.358(11) 0.959(4) 0.053(9) Uiso 1 1 d . . . . .
H2 H 0.7299(18) 0.580(8) 0.815(3) 0.040(7) Uiso 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
N5 N4 1.358(3) . ?
N5 C1 1.330(3) . ?
N4 N3 1.284(3) . ?
O7 N8 1.231(2) . ?
N8 O10 1.261(3) . ?
N8 O9 1.242(3) . ?
N2 C1 1.334(3) . ?
N2 N3 1.347(3) . ?
N2 H2 0.87(3) . ?
O11 H11 0.8200 . ?
O11 N12 1.402(3) . ?
C1 N6 1.331(3) . ?
N12 H12A 0.8684 . ?
N12 H12B 0.8687 . ?
N12 H12C 0.99(4) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?

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 N5 N4 105.63(19) . . ?
N3 N4 N5 111.26(18) . . ?
O7 N8 O10 119.5(2) . . ?
O7 N8 O9 120.5(2) . . ?
O9 N8 O10 120.01(19) . . ?
C1 N2 N3 109.08(16) . . ?
C1 N2 H2 130(2) . . ?
N3 N2 H2 121(2) . . ?
N12 O11 H11 109.5 . . ?
N5 C1 N2 107.8(2) . . ?
N5 C1 N6 126.9(2) . . ?
N6 C1 N2 125.2(2) . . ?
O11 N12 H12A 110.4 . . ?
O11 N12 H12B 110.2 . . ?
O11 N12 H12C 113(2) . . ?
H12A N12 H12B 108.5 . . ?
H12A N12 H12C 109.1 . . ?
H12B N12 H12C 105.6 . . ?
N4 N3 N2 106.20(19) . . ?
C1 N6 H6A 120.0 . . ?
C1 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_ajb-ii-232cslurried_auto
_database_code_depnum_ccdc_archive 'CCDC 2483547'
loop_
_audit_author_name
_audit_author_address
'Leila Foroughi'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-12 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'3-aminotriazole hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'3-amino-1h-1,2,4-triazole hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'H4 N O, N O3, C2 H4 N4'
_chemical_formula_sum            'C2 H8 N6 O4'
_chemical_formula_weight         180.14
_chemical_absolute_configuration ?
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.7993(3)
_cell_length_b                   3.60659(8)
_cell_length_c                   17.0814(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     726.91(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2177
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1360
_cell_measurement_theta_min      4.5180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2568
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.850
_diffrn_reflns_theta_min         5.179
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     52.00  89.00   0.50    0.27    --  109.86 -77.00  30.00   74
  2  ω     44.00  69.00   0.50    0.27    --  109.86 -61.00  90.00   50
  3  ω    102.00 127.00   0.50    0.27    --  109.86  45.00 -30.00   50
  4  ω     63.00  89.00   0.50    0.05    --   47.78 161.00  20.00   52
  5  ω    136.00 177.00   0.50    0.27    --  109.86  45.00 -30.00   82
  6  ω     37.00  62.00   0.50    0.27    --  109.86 -61.00-120.00   50
  7  ω      2.00  43.00   0.50    0.05    --   47.78 -37.00  60.00   82
  8  ω     24.00  49.00   0.50    0.05    --   47.78-117.00 141.00   50
  9  ω     50.00  90.00   0.50    0.27    --  109.86-117.00 141.00   80
 10  ω      5.00  30.00   0.50    0.05    --   47.78-100.00  40.00   50
 11  ω    -42.00  25.00   0.50    0.05    --  -47.78  37.00  60.00  134
 12  ω    -28.00  12.00   0.50    0.05    --  -47.78  37.00 -30.00   80
 13  ω    -97.00 -72.00   0.50    0.27    -- -106.00 117.00-130.00   50
 14  ω    -71.00 -33.00   0.50    0.27    -- -106.00  61.00   0.00   76
 15  ω    -68.00 -36.00   0.50    0.27    -- -106.00  61.00 -30.00   64
 16  ω   -160.00-135.00   0.50    0.27    -- -106.00 -26.00-142.00   50
 17  ω   -158.00-130.00   0.50    0.27    -- -106.00-100.00  40.00   56
 18  ω   -151.00-126.00   0.50    0.27    -- -106.00-117.00 141.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.530
_reflns_Friedel_fraction_full    0.616
_reflns_Friedel_fraction_max     0.544
_reflns_number_gt                1171
_reflns_number_total             1183
_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       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 403 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.107
_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)+(0.0570P)²+0.0413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0854
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C10(H10)
2.b X=CH2 refined with riding coordinates:
 N12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.26210(14) 0.8555(4) 0.51519(10) 0.0413(4) Uani 1 1 d . . . . .
H1 H 0.215075 0.796612 0.482107 0.062 Uiso 1 1 calc R U . . .
O3 O 0.5277(2) 0.7363(7) 0.59172(12) 0.0602(6) Uani 1 1 d . . . . .
N8 N 0.00690(15) 0.4358(5) 0.32360(13) 0.0375(4) Uani 1 1 d . . . . .
H8 H -0.012046 0.333888 0.280004 0.045 Uiso 1 1 calc R U . . .
O6 O 0.59963(17) 1.0420(7) 0.68868(14) 0.0592(5) Uani 1 1 d . . . . .
N11 N 0.11006(15) 0.6457(5) 0.41865(12) 0.0364(4) Uani 1 1 d . . . . .
O5 O 0.41860(16) 1.0014(7) 0.67419(12) 0.0585(5) Uani 1 1 d . . . . .
N4 N 0.51597(17) 0.9263(5) 0.65146(12) 0.0390(4) Uani 1 1 d . . . . .
N2 N 0.26347(16) 0.5890(5) 0.57524(13) 0.0415(5) Uani 1 1 d . . . . .
H2A H 0.258658 0.363258 0.554435 0.062 Uiso 1 1 calc R U . . .
H2B H 0.204882 0.626392 0.607091 0.062 Uiso 1 1 calc R U . . .
H2C H 0.327730 0.608459 0.602210 0.062 Uiso 1 1 calc R U . . .
N9 N -0.06805(16) 0.5821(6) 0.37679(14) 0.0414(5) Uani 1 1 d . . . . .
N12 N 0.20579(16) 0.3705(6) 0.31011(14) 0.0470(5) Uani 1 1 d . . . . .
H12A H 0.199822 0.269937 0.264651 0.056 Uiso 1 1 calc R U . . .
H12B H 0.271609 0.404527 0.330514 0.056 Uiso 1 1 calc R U . . .
C7 C 0.11304(17) 0.4737(6) 0.34895(13) 0.0337(5) Uani 1 1 d . . . . .
C10 C -0.0024(2) 0.7043(7) 0.43193(15) 0.0402(5) Uani 1 1 d . . . . .
H10 H -0.029671 0.821559 0.476610 0.048 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
O1 H1 0.8200 . ?
O1 N2 1.406(3) . ?
O3 N4 1.237(3) . ?
N8 H8 0.8600 . ?
N8 N9 1.373(3) . ?
N8 C7 1.332(3) . ?
O6 N4 1.246(3) . ?
N11 C7 1.343(3) . ?
N11 C10 1.363(3) . ?
O5 N4 1.243(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N9 C10 1.297(3) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N12 C7 1.333(3) . ?
C10 H10 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
N2 O1 H1 109.5 . . ?
N9 N8 H8 124.7 . . ?
C7 N8 H8 124.7 . . ?
C7 N8 N9 110.5(2) . . ?
C7 N11 C10 104.17(18) . . ?
O3 N4 O6 121.2(2) . . ?
O3 N4 O5 118.8(2) . . ?
O5 N4 O6 120.0(2) . . ?
O1 N2 H2A 109.5 . . ?
O1 N2 H2B 109.5 . . ?
O1 N2 H2C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C10 N9 N8 103.09(19) . . ?
H12A N12 H12B 120.0 . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
N8 C7 N11 108.1(2) . . ?
N8 C7 N12 125.6(2) . . ?
N12 C7 N11 126.3(2) . . ?
N11 C10 H10 123.0 . . ?
N9 C10 N11 114.1(2) . . ?
N9 C10 H10 123.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_ajb-ii-190aredo_auto
_database_code_depnum_ccdc_archive 'CCDC 2483550'
loop_
_audit_author_name
_audit_author_address
'Andrew Bennett'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-30 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-03-27
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'PDO bis-hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'pyrazine-1,4-dioxide bis-hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         '2(N O3), C4 H4 N2 O2, 2(H4 N O)'
_chemical_formula_sum            'C4 H12 N6 O10'
_chemical_formula_weight         152.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.98412(14)
_cell_length_b                   16.1555(4)
_cell_length_c                   6.29928(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.922(2)
_cell_angle_gamma                90
_cell_volume                     606.75(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2694
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1520
_cell_measurement_theta_min      5.4550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.465
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear amber'
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          .140
_exptl_crystal_size_mid          .110
_exptl_crystal_size_min          .110
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3693
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.913
_diffrn_reflns_theta_min         5.476
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  53.00   0.50    0.11    --   47.78 -96.00-169.00   68
  2  ω     87.00 112.00   0.50    0.94    --  109.86-125.00-120.00   50
  3  ω     43.00  69.00   0.50    0.94    --  109.86-125.00-120.00   52
  4  ω     48.00  73.00   0.50    0.94    --  109.86 -96.00-169.00   50
  5  ω     45.00  70.00   0.50    0.94    --  109.86 -61.00-150.00   50
  6  ω     37.00  63.00   0.50    0.94    --  109.86 -61.00 -90.00   52
  7  ω     44.00  70.00   0.50    0.94    --  109.86 -61.00 150.00   52
  8  ω    149.00 175.00   0.50    0.94    --  109.86 125.00  60.00   52
  9  ω     82.00 143.00   0.50    0.94    --  109.86 125.00  60.00  122
 10  ω    107.00 133.00   0.50    0.94    --  109.86  96.00 -60.00   52
 11  ω     94.00 165.00   0.50    0.94    --  109.86  77.00-120.00  142
 12  ω    -93.00 -17.00   0.50    0.11    --  -47.78 125.00 -60.00  152
 13  ω    -52.00 -27.00   0.50    0.11    --  -47.78  96.00 -60.00   50
 14  ω   -102.00 -52.00   0.50    0.94    -- -106.00 125.00   0.00  100
 15  ω    -99.00 -70.00   0.50    0.94    -- -106.00  96.00 -60.00   58
 16  ω    -66.00 -34.00   0.50    0.94    -- -106.00  61.00-120.00   64
 17  ω    -65.00 -39.00   0.50    0.94    -- -106.00  61.00  90.00   52
 18  ω    -70.00 -40.00   0.50    0.94    -- -106.00  61.00 120.00   60
 19  ω    -69.00 -34.00   0.50    0.94    -- -106.00  61.00 150.00   70
 20  ω    -92.00 -33.00   0.50    0.11    --  -47.78 -57.00  90.00  118
 21  ω    -67.00 -30.00   0.50    0.11    --  -47.78 -77.00-150.00   74
 22  ω   -115.00 -71.00   0.50    0.11    --  -47.78 -77.00-150.00   88
 23  ω   -169.00 -84.00   0.50    0.94    -- -106.00 -96.00-169.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2368992000
_diffrn_orient_matrix_UB_12      0.0378163000
_diffrn_orient_matrix_UB_13      -0.0074619000
_diffrn_orient_matrix_UB_21      0.0998624000
_diffrn_orient_matrix_UB_22      0.0811872000
_diffrn_orient_matrix_UB_23      0.0949986000
_diffrn_orient_matrix_UB_31      0.0258271000
_diffrn_orient_matrix_UB_32      0.0328021000
_diffrn_orient_matrix_UB_33      -0.2261574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1127
_reflns_number_total             1236
_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       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.136
_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)+(0.0749P)²+0.4108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6)
2.c Tetrahedral OH refined with riding coordinates:
 O9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O1 O 1.1105(3) 0.33219(11) 0.0825(3) 0.0557(6) Uani 1 1 d . . . . .
O8 O 0.2994(3) 0.51381(11) 0.2110(3) 0.0587(6) Uani 1 1 d . . . . .
O4 O 0.9202(3) 0.22776(12) 0.1826(4) 0.0631(6) Uani 1 1 d . . . . .
N5 N 0.1522(3) 0.50649(10) 0.3520(3) 0.0383(5) Uani 1 1 d . . . . .
N2 N 1.1036(3) 0.25979(12) 0.1477(3) 0.0427(5) Uani 1 1 d . . . . .
N10 N 0.5993(4) 0.35668(14) 0.0713(3) 0.0491(6) Uani 1 1 d . . . . .
H10A H 0.691416 0.315263 0.080187 0.059 Uiso 1 1 d R U . . .
H10B H 0.463664 0.337961 0.054021 0.059 Uiso 1 1 d R U . . .
O3 O 1.2777(4) 0.22043(14) 0.1821(4) 0.0773(7) Uani 1 1 d . . . . .
O9 O 0.6285(4) 0.40178(18) 0.2507(3) 0.0804(8) Uani 1 1 d . . . . .
H9 H 0.523966 0.434366 0.255289 0.121 Uiso 1 1 calc R U . . .
C7 C 0.1735(4) 0.44681(13) 0.5025(4) 0.0403(5) Uani 1 1 d . . . . .
H7 H 0.292495 0.409690 0.504722 0.048 Uiso 1 1 calc R U . . .
C6 C -0.0222(4) 0.55930(13) 0.3495(4) 0.0396(5) Uani 1 1 d . . . . .
H6 H -0.039173 0.600248 0.245629 0.047 Uiso 1 1 calc R U . . .
H10C H 0.655(5) 0.3819(19) -0.039(5) 0.059(8) Uiso 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 N2 1.242(3) . ?
O8 N5 1.309(3) . ?
O4 N2 1.250(3) . ?
N5 C7 1.350(3) . ?
N5 C6 1.347(3) . ?
N2 O3 1.224(3) . ?
N10 O9 1.343(3) . ?
C7 C6 1.358(3) 3_566 ?

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
O8 N5 C7 120.82(19) . . ?
O8 N5 C6 120.06(18) . . ?
C6 N5 C7 119.12(19) . . ?
O1 N2 O4 120.2(2) . . ?
O3 N2 O1 119.7(2) . . ?
O3 N2 O4 120.1(2) . . ?
N5 C7 C6 120.4(2) . 3_566 ?
N5 C6 C7 120.51(19) . 3_566 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_ajb-ii-201ahantriazolone_auto
_database_code_depnum_ccdc_archive 'CCDC 2483545'
loop_
_audit_author_name
_audit_author_address
'Leila Foroughi'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-12 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'triazolone hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'1H-1,2,4-triazol-3(2H)-one hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'N O3, C2 H3 N3 O, H4 N O'
_chemical_formula_sum            'C2 H7 N5 O5'
_chemical_formula_weight         181.13
_chemical_absolute_configuration ?
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   18.1310(4)
_cell_length_b                   3.67557(10)
_cell_length_c                   10.7747(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     718.05(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1953
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.5830
_cell_measurement_theta_min      2.4300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2614
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.512
_diffrn_reflns_theta_min         4.878
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     61.00  86.00   0.50    0.23    --   47.66-125.00  90.00   50
  2  ω     21.00  46.00   0.50    0.23    --   47.66-113.00 169.00   50
  3  ω     59.00  96.00   0.50    1.44    --  109.86-113.00 169.00   74
  4  ω     56.00  82.00   0.50    1.44    --  109.86-105.00  72.00   52
  5  ω     37.00  63.00   0.50    1.44    --  109.86 -61.00 -90.00   52
  6  ω     45.00  71.00   0.50    1.44    --  109.86 -61.00-150.00   52
  7  ω     96.00 178.00   0.50    1.44    --  109.86  15.00   0.00  164
  8  ω      3.00  28.00   0.50    0.23    --   47.66 -24.00-103.00   50
  9  ω    -60.00 -28.00   0.50    0.23    --  -47.66 -77.00   0.00   64
 10  ω   -116.00 -63.00   0.50    0.23    --  -47.66 -77.00   0.00  106
 11  ω   -138.00-113.00   0.50    1.44    -- -106.00 -24.00-103.00   50
 12  ω    -64.00 -39.00   0.50    0.23    --  -47.66 105.00 173.00   50
 13  ω     -4.00  26.00   0.50    0.23    --  -47.66  37.00 120.00   60
 14  ω    -43.00  -9.00   0.50    0.23    --  -47.66  37.00 120.00   68
 15  ω    -62.00 -36.00   0.50    1.44    -- -106.00 125.00   0.00   52
 16  ω    -64.00 -39.00   0.50    1.44    -- -106.00 125.00  90.00   50
 17  ω   -112.00 -86.00   0.50    1.44    -- -106.00 125.00  90.00   52
 18  ω   -106.00 -80.00   0.50    1.44    -- -106.00 125.00   0.00   52
 19  ω    -97.00 -72.00   0.50    1.44    -- -106.00 113.00 -98.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.717
_reflns_Friedel_fraction_max     0.634
_reflns_number_gt                1202
_reflns_number_total             1235
_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       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(17)
_refine_ls_extinction_coef       0.0074(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0747
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N9(H9), C8(H8), N6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O -0.34821(9) -0.1483(6) -0.0562(3) 0.0623(6) Uani 1 1 d . . . . .
O4 O -0.44304(12) 0.1402(6) 0.01402(19) 0.0593(6) Uani 1 1 d . . . . .
O10 O -0.27411(9) 0.3976(6) 0.2165(2) 0.0521(5) Uani 1 1 d . . . . .
O11 O -0.44373(9) 0.6494(5) 0.2684(2) 0.0469(5) Uani 1 1 d . . . . .
H11 H -0.480785 0.762326 0.288929 0.070 Uiso 1 1 calc R U . . .
N12 N -0.38548(10) 0.8949(5) 0.2477(2) 0.0358(4) Uani 1 1 d . . . . .
H12A H -0.344753 0.776951 0.233522 0.043 Uiso 1 1 d R U . . .
H12B H -0.394813 1.031783 0.183664 0.043 Uiso 1 1 d R U . . .
N9 N -0.15043(11) 0.4950(6) 0.1670(2) 0.0395(4) Uani 1 1 d . . . . .
H9 H -0.134680 0.595699 0.234011 0.047 Uiso 1 1 calc R U . . .
C5 C -0.22044(12) 0.3820(6) 0.1456(2) 0.0358(5) Uani 1 1 d . . . . .
O3 O -0.44454(10) -0.0881(6) -0.16946(19) 0.0526(5) Uani 1 1 d . . . . .
C8 C -0.10959(12) 0.4222(8) 0.0651(3) 0.0419(5) Uani 1 1 d . . . . .
H8 H -0.059712 0.477035 0.057623 0.050 Uiso 1 1 calc R U . . .
N2 N -0.41170(9) -0.0294(6) -0.0692(2) 0.0377(4) Uani 1 1 d . . . . .
N7 N -0.14793(11) 0.2685(7) -0.0202(2) 0.0438(5) Uani 1 1 d . . . . .
N6 N -0.21759(10) 0.2447(6) 0.0305(2) 0.0401(5) Uani 1 1 d . . . . .
H6 H -0.254914 0.152439 -0.007400 0.048 Uiso 1 1 calc R U . . .
H12C H -0.3755(15) 1.030(9) 0.313(3) 0.035(7) Uiso 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 N2 1.239(3) . ?
O4 N2 1.231(3) . ?
O10 C5 1.238(3) . ?
O11 H11 0.8200 . ?
O11 N12 1.407(3) . ?
N12 H12A 0.8697 . ?
N12 H12B 0.8702 . ?
N12 H12C 0.88(3) . ?
N9 H9 0.8600 . ?
N9 C5 1.355(3) . ?
N9 C8 1.351(3) . ?
C5 N6 1.340(3) . ?
O3 N2 1.253(3) . ?
C8 H8 0.9300 . ?
C8 N7 1.283(4) . ?
N7 N6 1.379(3) . ?
N6 H6 0.8600 . ?

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
N12 O11 H11 109.5 . . ?
O11 N12 H12A 110.2 . . ?
O11 N12 H12B 110.5 . . ?
O11 N12 H12C 112.8(18) . . ?
H12A N12 H12B 108.3 . . ?
H12A N12 H12C 104.3 . . ?
H12B N12 H12C 110.4 . . ?
C5 N9 H9 125.8 . . ?
C8 N9 H9 125.8 . . ?
C8 N9 C5 108.3(2) . . ?
O10 C5 N9 128.1(2) . . ?
O10 C5 N6 128.2(2) . . ?
N6 C5 N9 103.7(2) . . ?
N9 C8 H8 124.1 . . ?
N7 C8 N9 111.9(2) . . ?
N7 C8 H8 124.1 . . ?
O1 N2 O3 118.6(2) . . ?
O4 N2 O1 121.7(2) . . ?
O4 N2 O3 119.74(19) . . ?
C8 N7 N6 103.9(2) . . ?
C5 N6 N7 112.22(19) . . ?
C5 N6 H6 123.9 . . ?
N7 N6 H6 123.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_ajb-ii-74bredo_auto
_database_code_depnum_ccdc_archive 'CCDC 2483544'
loop_
_audit_author_name
_audit_author_address
'Leila Foroughi'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-12 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'BPDO Hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'4,4?-bipyridine-N,N?-dioxide hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'C10 H8 N2 O2, H4 N O, N O3'
_chemical_formula_sum            'C10 H12 N4 O6'
_chemical_formula_weight         284.24
_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 0.0181 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.2509(3)
_cell_length_b                   16.9335(7)
_cell_length_c                   10.1908(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.392(3)
_cell_angle_gamma                90
_cell_volume                     1237.86(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2530
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3530
_cell_measurement_theta_min      5.2200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear amber'
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Isopropanol'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8098
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.415
_diffrn_reflns_theta_min         5.106
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  69.00   0.50    5.83    --   46.53-111.00 119.00   52
  2  ω    -76.00 -30.00   0.50    5.83    --  -47.78 111.00-146.00   92
  3  ω    103.00 128.00   0.50   26.41    --  104.41 111.00-146.00   50
  4  ω     63.00  89.00   0.50   26.41    --  104.41-111.00 119.00   52
  5  ω    -97.00 -72.00   0.50   26.41    -- -105.66 111.00-146.00   50
  6  ω   -133.00-108.00   0.50   26.41    -- -105.66-111.00 119.00   50
  7  ω    -18.00  30.00   0.50    5.83    --   46.53 -19.00   0.00   96
  8  ω   -119.00 -49.00   0.50    5.83    --  -47.78 -57.00 120.00  140
  9  ω    -60.00  20.00   0.50    5.83    --  -47.78  57.00-150.00  160
 10  ω    -28.00   3.00   0.50    5.83    --  -47.78  19.00 -60.00   62
 11  ω     35.00  79.00   0.50   26.41    --  104.41 -77.00-120.00   88
 12  ω     67.00 105.00   0.50   26.41    --  104.41 -94.00 120.00   76
 13  ω     35.00  69.00   0.50   26.41    --  104.41 -61.00  30.00   68
 14  ω     36.00  71.00   0.50   26.41    --  104.41 -61.00 -60.00   70
 15  ω     62.00 103.00   0.50   26.41    --  104.41 -94.00-180.00   82
 16  ω    -63.00 -37.00   0.50   26.41    -- -105.66  61.00 120.00   52
 17  ω    -88.00 -34.00   0.50   26.41    -- -105.66  77.00  30.00  108
 18  ω   -168.00 -92.00   0.50   26.41    -- -105.66 -15.00-180.00  152
 19  ω   -100.00 -40.00   0.50   26.41    -- -105.66  77.00-150.00  120
 20  ω   -148.00 -93.00   0.50   26.41    -- -105.66 -77.00  90.00  110
 21  ω    -63.00 -38.00   0.50   26.41    -- -105.66  61.00 150.00   50
 22  ω   -174.00-103.00   0.50   26.41    -- -105.66 -45.00 150.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1977
_reflns_number_total             2494
_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       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0759P)²+0.3910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1519
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C5(H5), C11(H11), C7(H7), C2(H2), C1(H1), C10(H10)
2.b Idealised Me refined as rotating group:
 N20(H20A,H20B,H20C)
2.c Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O13 O 0.3313(3) 0.44167(11) 1.23100(14) 0.0548(5) Uani 1 1 d . . . . .
O14 O 0.0534(3) 0.62849(10) 0.32744(14) 0.0544(5) Uani 1 1 d . . . . .
N12 N 0.2927(3) 0.46658(11) 1.10750(16) 0.0404(4) Uani 1 1 d . . . . .
N6 N 0.0993(3) 0.60643(11) 0.45241(16) 0.0408(4) Uani 1 1 d . . . . .
O19 O -0.0663(3) 0.76872(13) 0.2798(2) 0.0731(6) Uani 1 1 d . . . . .
H19 H -0.049288 0.722492 0.302363 0.110 Uiso 1 1 calc R U . . .
N20 N 0.0662(3) 0.79109(13) 0.20002(19) 0.0545(5) Uani 1 1 d . . . . .
H20A H 0.018400 0.785291 0.115035 0.065 Uiso 1 1 calc R U . . .
H20B H 0.166945 0.760828 0.218518 0.065 Uiso 1 1 calc R U . . .
H20C H 0.097417 0.841400 0.215725 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2200(3) 0.52285(12) 0.84899(19) 0.0369(5) Uani 1 1 d . . . . .
C3 C 0.1822(3) 0.55309(12) 0.71131(19) 0.0369(5) Uani 1 1 d . . . . .
C4 C 0.2559(3) 0.51702(14) 0.6076(2) 0.0432(5) Uani 1 1 d . . . . .
H4 H 0.335075 0.473918 0.625235 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2850(3) 0.44618(14) 0.8770(2) 0.0421(5) Uani 1 1 d . . . . .
H8 H 0.304895 0.412880 0.807878 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2138(3) 0.54386(14) 0.4808(2) 0.0440(5) Uani 1 1 d . . . . .
H5 H 0.264322 0.518844 0.412974 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2279(3) 0.54106(14) 1.0845(2) 0.0443(5) Uani 1 1 d . . . . .
H11 H 0.207784 0.573139 1.155136 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3197(3) 0.41946(13) 1.0049(2) 0.0434(5) Uani 1 1 d . . . . .
H7 H 0.362471 0.368136 1.021584 0.052 Uiso 1 1 calc R U . . .
C2 C 0.0687(3) 0.61827(14) 0.6791(2) 0.0447(5) Uani 1 1 d . . . . .
H2 H 0.018412 0.644778 0.745572 0.054 Uiso 1 1 calc R U . . .
C1 C 0.0296(4) 0.64409(14) 0.5506(2) 0.0468(5) Uani 1 1 d . . . . .
H1 H -0.045962 0.688161 0.530976 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1921(3) 0.56914(13) 0.9574(2) 0.0435(5) Uani 1 1 d . . . . .
H10 H 0.148085 0.620455 0.943079 0.052 Uiso 1 1 calc R U . . .
O1 O 0.4198(3) 0.70341(12) 0.23513(17) 0.0635(5) Uani 1 1 d . . . . .
N2 N 0.4712(3) 0.70627(12) 0.3567(2) 0.0497(5) Uani 1 1 d . . . . .
O2 O 0.4016(3) 0.75649(12) 0.42489(18) 0.0669(6) Uani 1 1 d . . . . .
O3 O 0.5912(4) 0.66169(15) 0.4125(2) 0.0895(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
O13 N12 1.318(2) . ?
O14 N6 1.322(2) . ?
N12 C11 1.354(3) . ?
N12 C7 1.352(3) . ?
N6 C5 1.351(3) . ?
N6 C1 1.345(3) . ?
O19 H19 0.8200 . ?
O19 N20 1.398(3) . ?
N20 H20A 0.8900 . ?
N20 H20B 0.8900 . ?
N20 H20C 0.8900 . ?
C9 C3 1.481(3) . ?
C9 C8 1.396(3) . ?
C9 C10 1.393(3) . ?
C3 C4 1.393(3) . ?
C3 C2 1.388(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.368(3) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.368(3) . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.371(3) . ?
C1 H1 0.9300 . ?
C10 H10 0.9300 . ?
O1 N2 1.242(3) . ?
N2 O2 1.250(3) . ?
N2 O3 1.227(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
O13 N12 C11 118.89(18) . . ?
O13 N12 C7 120.98(18) . . ?
C7 N12 C11 120.12(18) . . ?
O14 N6 C5 119.20(18) . . ?
O14 N6 C1 120.88(19) . . ?
C1 N6 C5 119.90(18) . . ?
N20 O19 H19 109.5 . . ?
O19 N20 H20A 109.5 . . ?
O19 N20 H20B 109.5 . . ?
O19 N20 H20C 109.5 . . ?
H20A N20 H20B 109.5 . . ?
H20A N20 H20C 109.5 . . ?
H20B N20 H20C 109.5 . . ?
C8 C9 C3 121.69(19) . . ?
C10 C9 C3 121.92(19) . . ?
C10 C9 C8 116.39(19) . . ?
C4 C3 C9 121.9(2) . . ?
C2 C3 C9 121.35(19) . . ?
C2 C3 C4 116.70(19) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
N6 C5 C4 120.7(2) . . ?
N6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
N12 C11 H11 120.0 . . ?
N12 C11 C10 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
N12 C7 C8 120.9(2) . . ?
N12 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
N6 C1 C2 120.8(2) . . ?
N6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.7(2) . . ?
C11 C10 H10 119.1 . . ?
O1 N2 O2 119.6(2) . . ?
O3 N2 O1 121.9(2) . . ?
O3 N2 O2 118.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_ajb-ii-65b_auto
_database_code_depnum_ccdc_archive 'CCDC 2483548'
loop_
_audit_author_name
_audit_author_address
'Andrew Bennett'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-30 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-30
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'3,5-diamino-1h-1,2,4-triazole hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'3,5-diamino-1h-1,2,4-triazole hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'H4 N O, N O3, C2 H5 N5'
_chemical_formula_sum            'C2 H9 N7 O4'
_chemical_formula_weight         195.16
_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 0.0181 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.5441(4)
_cell_length_b                   8.1023(3)
_cell_length_c                   19.1221(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.452(4)
_cell_angle_gamma                90
_cell_volume                     1588.81(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5753
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7180
_cell_measurement_theta_min      4.7720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10105
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.325
_diffrn_reflns_theta_min         4.756
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  13.00   0.50    0.21    --   46.53 -44.00 141.00   64
  2  ω     32.00  57.00   0.50    1.58    --  104.41 -61.00  60.00   50
  3  ω    -22.00  19.00   0.50    0.21    --   46.53 -19.00 -60.00   82
  4  ω     96.00 178.00   0.50    1.58    --  104.41  15.00  60.00  164
  5  ω    133.00 173.00   0.50    1.58    --  104.41  44.00 -67.00   80
  6  ω     66.00  92.00   0.50    0.21    --   46.53  44.00 -67.00   52
  7  ω     -2.00  23.00   0.50    0.21    --  -47.78  57.00-180.00   50
  8  ω    -60.00  -9.00   0.50    0.21    --  -47.78  57.00-180.00  102
  9  ω    -37.00 -12.00   0.50    0.21    --  -47.78  44.00 -67.00   50
 10  ω    -29.00  17.00   0.50    0.21    --  -47.78  19.00  90.00   92
 11  ω    -67.00 -42.00   0.50    1.58    -- -105.66  61.00 120.00   50
 12  ω    -71.00 -36.00   0.50    1.58    -- -105.66  61.00  90.00   70
 13  ω    -71.00 -43.00   0.50    1.58    -- -105.66  61.00 150.00   56
 14  ω    -71.00 -37.00   0.50    1.58    -- -105.66  61.00  60.00   68
 15  ω    -70.00 -36.00   0.50    1.58    -- -105.66  61.00  30.00   68
 16  ω    -84.00 -40.00   0.50    1.58    -- -105.66  77.00 -90.00   88
 17  ω    -61.00 -33.00   0.50    1.58    -- -105.66  77.00-150.00   56
 18  ω    -66.00 -40.00   0.50    1.58    -- -105.66  61.00-120.00   52
 19  ω   -171.00-102.00   0.50    1.58    -- -105.66 -30.00   0.00  138
 20  ω   -168.00 -93.00   0.50    1.58    -- -105.66 -45.00 120.00  150
 21  ω   -117.00 -92.00   0.50    1.58    -- -105.66 -44.00 141.00   50
 22  ω    -85.00 -60.00   0.50    0.21    --  -47.78 -44.00 141.00   50
 23  ω   -114.00 -33.00   0.50    0.21    --  -47.78 -57.00 -60.00  162
 24  ω   -146.00 -98.00   0.50    1.58    -- -105.66 -45.00-180.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2773
_reflns_number_total             3180
_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       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.113
_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)+(0.0681P)²+0.3263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1231
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Rotating group:
 N19(H19A,H19B), N26(H26A,H26B), N18(H18A,H18B), N25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N21(H21), N15A(H15A)
2.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O 0.08852(10) 0.32924(15) 0.75493(6) 0.0389(3) Uani 1 1 d . . . . .
O3 O 0.61689(12) 0.31933(16) 0.51368(6) 0.0448(3) Uani 1 1 d . . . . .
O5 O 0.70037(12) 0.70724(14) 0.57095(6) 0.0442(3) Uani 1 1 d . . . . .
O9 O 0.19671(12) 0.71325(15) 0.81050(7) 0.0447(3) Uani 1 1 d . . . . .
O8 O 0.79880(12) 0.73705(17) 0.48382(6) 0.0458(3) Uani 1 1 d . . . . .
N17 N -0.02099(11) 0.30788(16) 0.86385(6) 0.0306(3) Uani 1 1 d . . . . .
N6 N 0.74333(12) 0.79786(16) 0.52790(7) 0.0343(3) Uani 1 1 d . . . . .
N2 N 0.21808(12) 0.37007(17) 0.79009(7) 0.0350(3) Uani 1 1 d . . . . .
H2A H 0.270830 0.349234 0.760963 0.052 Uiso 1 1 calc R U . . .
H2B H 0.242449 0.309930 0.829901 0.052 Uiso 1 1 calc R U . . .
H2C H 0.222486 0.476734 0.801516 0.052 Uiso 1 1 calc R U . . .
O7 O 0.72866(15) 0.95004(15) 0.53164(8) 0.0548(4) Uani 1 1 d . . . . .
N24 N 0.48779(11) 0.24440(17) 0.61275(6) 0.0329(3) Uani 1 1 d . . . . .
O12 O 0.30650(13) 0.7538(2) 0.72897(7) 0.0577(4) Uani 1 1 d . . . . .
N10 N 0.25043(12) 0.80926(18) 0.77394(7) 0.0376(3) Uani 1 1 d . . . . .
O11 O 0.24662(15) 0.95918(16) 0.78415(8) 0.0580(4) Uani 1 1 d . . . . .
N4 N 0.74191(13) 0.37225(17) 0.55138(7) 0.0375(3) Uani 1 1 d . . . . .
H4A H 0.798603 0.357545 0.523968 0.056 Uiso 1 1 calc R U . . .
H4B H 0.766945 0.313764 0.591631 0.056 Uiso 1 1 calc R U . . .
H4C H 0.738872 0.478747 0.562276 0.056 Uiso 1 1 calc R U . . .
N22 N 0.36144(13) 0.28348(18) 0.69130(8) 0.0407(3) Uani 1 1 d . . . . .
N21 N 0.39113(13) 0.11779(18) 0.68653(8) 0.0428(3) Uani 1 1 d . . . . .
H21 H 0.365332 0.039415 0.710204 0.051 Uiso 1 1 calc R U . . .
N19 N -0.05519(15) 0.59894(17) 0.87466(8) 0.0460(4) Uani 1 1 d . . . . .
H19A H -0.052881 0.606136 0.830076 0.055 Uiso 1 1 d R U . . .
H19B H -0.120296 0.654727 0.881968 0.055 Uiso 1 1 d R U . . .
N26 N 0.42344(15) 0.51834(19) 0.63425(8) 0.0475(4) Uani 1 1 d . . . . .
H26A H 0.418361 0.536296 0.589386 0.057 Uiso 1 1 d R U . . .
H26B H 0.357986 0.563356 0.646554 0.057 Uiso 1 1 d R U . . .
N18 N -0.02160(16) 0.01861(18) 0.89034(8) 0.0475(4) Uani 1 1 d . . . . .
H18A H -0.069344 -0.049473 0.907903 0.057 Uiso 1 1 d R U . . .
H18B H -0.033027 -0.000224 0.844772 0.057 Uiso 1 1 d R U . . .
C13 C -0.05656(14) 0.17767(19) 0.90064(8) 0.0314(3) Uani 1 1 d . . . . .
C16 C -0.06845(14) 0.43866(19) 0.89201(7) 0.0321(3) Uani 1 1 d . . . . .
N25 N 0.51507(16) -0.0486(2) 0.62538(10) 0.0538(4) Uani 1 1 d . . . . .
H25A H 0.458546 -0.126853 0.624115 0.065 Uiso 1 1 d R U . . .
H25B H 0.534504 -0.043321 0.583820 0.065 Uiso 1 1 d R U . . .
C20 C 0.46527(14) 0.0987(2) 0.63995(8) 0.0358(3) Uani 1 1 d . . . . .
C23 C 0.42197(13) 0.3526(2) 0.64594(8) 0.0325(3) Uani 1 1 d . . . . .
H1 H 0.044(2) 0.319(3) 0.7900(14) 0.066(7) Uiso 1 1 d . . . . .
H3 H 0.576(2) 0.294(3) 0.5484(14) 0.071(7) Uiso 1 1 d . . . . .
N15A N -0.12688(13) 0.38997(16) 0.94267(7) 0.0383(3) Uani 1 1 d . . . A 2
H15A H -0.163160 0.454542 0.967945 0.046 Uiso 1 1 calc R U . A 2
N14A N -0.12102(13) 0.22016(17) 0.94898(7) 0.0376(3) Uani 1 1 d . . . A 2


_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 N2 1.4143(16) . ?
O1 H1 0.91(3) . ?
O3 N4 1.4139(18) . ?
O3 H3 0.90(3) . ?
O5 N6 1.2631(17) . ?
O9 N10 1.2646(18) . ?
O8 N6 1.2349(17) . ?
N17 C13 1.3680(19) . ?
N17 C16 1.337(2) . ?
N6 O7 1.2468(19) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N24 C20 1.334(2) . ?
N24 C23 1.3633(19) . ?
O12 N10 1.2358(18) . ?
N10 O11 1.232(2) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N22 N21 1.386(2) . ?
N22 C23 1.316(2) . ?
N21 H21 0.8600 . ?
N21 C20 1.324(2) . ?
N19 H19A 0.8604 . ?
N19 H19B 0.8601 . ?
N19 C16 1.356(2) . ?
N26 H26A 0.8594 . ?
N26 H26B 0.8604 . ?
N26 C23 1.362(2) . ?
N18 H18A 0.8655 . ?
N18 H18B 0.8650 . ?
N18 C13 1.367(2) . ?
C13 N14A 1.3143(19) . ?
C16 N15A 1.3235(19) . ?
N25 H25A 0.8665 . ?
N25 H25B 0.8667 . ?
N25 C20 1.359(2) . ?
N15A H15A 0.8600 . ?
N15A N14A 1.3812(19) . ?

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 O1 H1 106.1(15) . . ?
N4 O3 H3 104.1(16) . . ?
C16 N17 C13 103.35(12) . . ?
O8 N6 O5 120.77(14) . . ?
O8 N6 O7 121.24(14) . . ?
O7 N6 O5 117.99(13) . . ?
O1 N2 H2A 109.5 . . ?
O1 N2 H2B 109.5 . . ?
O1 N2 H2C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C20 N24 C23 103.40(12) . . ?
O12 N10 O9 120.62(16) . . ?
O11 N10 O9 118.91(14) . . ?
O11 N10 O12 120.47(15) . . ?
O3 N4 H4A 109.5 . . ?
O3 N4 H4B 109.5 . . ?
O3 N4 H4C 109.5 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C23 N22 N21 102.55(13) . . ?
N22 N21 H21 125.2 . . ?
C20 N21 N22 109.60(13) . . ?
C20 N21 H21 125.2 . . ?
H19A N19 H19B 109.5 . . ?
C16 N19 H19A 109.6 . . ?
C16 N19 H19B 109.4 . . ?
H26A N26 H26B 109.5 . . ?
C23 N26 H26A 109.3 . . ?
C23 N26 H26B 109.4 . . ?
H18A N18 H18B 108.7 . . ?
C13 N18 H18A 110.1 . . ?
C13 N18 H18B 109.4 . . ?
N18 C13 N17 122.52(13) . . ?
N14A C13 N17 114.09(13) . . ?
N14A C13 N18 123.30(14) . . ?
N17 C16 N19 126.22(14) . . ?
N15A C16 N17 109.88(13) . . ?
N15A C16 N19 123.84(14) . . ?
H25A N25 H25B 108.6 . . ?
C20 N25 H25A 110.6 . . ?
C20 N25 H25B 109.2 . . ?
N24 C20 N25 125.83(15) . . ?
N21 C20 N24 110.20(14) . . ?
N21 C20 N25 123.90(16) . . ?
N22 C23 N24 114.25(14) . . ?
N22 C23 N26 123.63(15) . . ?
N26 C23 N24 122.08(14) . . ?
C16 N15A H15A 125.0 . . ?
C16 N15A N14A 109.99(12) . . ?
N14A N15A H15A 125.0 . . ?
C13 N14A N15A 102.68(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_hanpa5-22-25_auto
_database_code_depnum_ccdc_archive 'CCDC 2483546'
loop_
_audit_author_name
_audit_author_address
'Andrew Bennett'
;University of Michigan
United States of America
;
_audit_update_record             
;
2025-12-30 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-30
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'1,10-phenanthroline hydroxylammonium nitrate cocrystal'
_chemical_name_systematic        
'1,10-phenanthroline hydroxylammonium nitrate cocrystal'
_chemical_formula_moiety         'N O3, H4 N O, C12 H8 N2'
_chemical_formula_sum            'C12 H12 N4 O4'
_chemical_formula_weight         276.26
_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 0.0181 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4611(3)
_cell_length_b                   10.8576(3)
_cell_length_c                   11.9263(3)
_cell_angle_alpha                75.709(2)
_cell_angle_beta                 86.876(2)
_cell_angle_gamma                72.457(3)
_cell_volume                     1251.36(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.5940
_cell_measurement_theta_min      3.8150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Isopropanol'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12788
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         3.826
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -31.00   0.50    0.76    --  -47.78  74.00-159.00   70
  2  ω   -110.00 -36.00   0.50    0.76    --  -47.78 -74.00  72.00  148
  3  ω     -7.00  19.00   0.50    0.76    --  -47.78  74.00-159.00   52
  4  ω   -154.00-125.00   0.50    3.93    -- -106.00 -74.00  72.00   58
  5  ω    -64.00 -38.00   0.50    3.93    -- -106.00  74.00-159.00   52
  6  ω   -122.00 -96.00   0.50    3.93    -- -106.00 -74.00  72.00   52
  7  ω     37.00  93.00   0.50    3.93    --  109.86 -74.00  72.00  112
  8  ω    135.00 164.00   0.50    3.93    --  109.86  74.00-159.00   58
  9  ω    -27.00  11.00   0.50    0.76    --  -47.78  19.00 150.00   76
 10  ω    -28.00  27.00   0.50    0.76    --  -47.78  19.00-150.00  110
 11  ω    -16.00  67.00   0.50    0.76    --   47.78 -74.00  72.00  166
 12  ω      8.00  38.00   0.50    0.76    --   47.78 -37.00-120.00   60
 13  ω    -22.00  29.00   0.50    0.76    --   47.78 -19.00 -90.00  102
 14  ω     41.00 111.00   0.50    0.76    --   47.78  74.00-159.00  140
 15  ω    -24.00  28.00   0.50    0.76    --   47.78 -19.00 -30.00  104
 16  ω   -176.00 -98.00   0.50    3.93    -- -106.00 -15.00-120.00  156
 17  ω    -71.00 -33.00   0.50    3.93    -- -106.00  61.00-180.00   76
 18  ω    -62.00 -37.00   0.50    3.93    -- -106.00  61.00  30.00   50
 19  ω   -112.00 -45.00   0.50    3.93    -- -106.00 125.00-120.00  134
 20  ω   -158.00 -92.00   0.50    3.93    -- -106.00 -15.00 -90.00  132
 21  ω   -111.00 -74.00   0.50    3.93    -- -106.00 125.00 -60.00   74
 22  ω   -108.00 -82.00   0.50    3.93    -- -106.00 110.00  21.86   52
 23  ω   -170.00 -95.00   0.50    3.93    -- -106.00 -45.00-150.00  150
 24  ω   -176.00 -97.00   0.50    3.93    -- -106.00 -45.00   0.00  158
 25  ω    -64.00 -33.00   0.50    3.93    -- -106.00  61.00  60.00   62
 26  ω   -112.00 -53.00   0.50    3.93    -- -106.00 125.00  90.00  118
 27  ω    -70.00 -44.00   0.50    3.93    -- -106.00  61.00 -30.00   52
 28  ω    -62.00 -37.00   0.50    3.93    -- -106.00 125.00 -60.00   50
 29  ω   -112.00 -86.00   0.50    3.93    -- -106.00 125.00 150.00   52
 30  ω     50.00  99.00   0.50    3.93    --  109.86 -77.00 -60.00   98
 31  ω     38.00  70.00   0.50    3.93    --  109.86 -61.00 150.00   64
 32  ω     42.00  89.00   0.50    3.93    --  109.86 -94.00 -90.00   94
 33  ω     49.00 106.00   0.50    3.93    --  109.86 -94.00-180.00  114
 34  ω     75.00 101.00   0.50    3.93    --  109.86-125.00  90.00   52
 35  ω    144.00 175.00   0.50    3.93    --  109.86  30.00 120.00   62
 36  ω     60.00  97.00   0.50    3.93    --  109.86 -77.00-180.00   74
 37  ω     40.00  95.00   0.50    3.93    --  109.86-100.00  73.00  110
 38  ω     39.00  69.00   0.50    3.93    --  109.86 -61.00-150.00   60
 39  ω    103.00 140.00   0.50    3.93    --  109.86  30.00 120.00   74
 40  ω    144.00 169.00   0.50    3.93    --  109.86  45.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3605
_reflns_number_total             4471
_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       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0834P)²+0.1619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1436
_refine_special_details          
'19 outlying reflections were omitted where the |Error/esd| is greater than 10.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N6(H6A,H6B), N40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C14(H14), C13(H13), C28(H28), C15(H15), C29(H29), C11(H11),
 C35(H35), C17(H17), C37(H37), C18(H18), C19(H19), C10(H10), C31(H31), C32(H32),
  C36(H36)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5), O39(H39)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O 0.68046(13) 0.51481(13) 0.52562(12) 0.0640(4) Uani 1 1 d . . . . .
O5 O 0.83554(13) 0.24567(14) 0.74914(13) 0.0665(4) Uani 1 1 d . . . . .
H5 H 0.891506 0.177904 0.739451 0.100 Uiso 1 1 calc R U . . .
N16 N 0.21800(13) 0.56012(13) 0.85824(11) 0.0457(3) Uani 1 1 d . . . . .
O21 O 0.50063(14) 0.25801(15) 0.84841(14) 0.0723(4) Uani 1 1 d . . . . .
N20 N -0.03681(14) 0.54454(14) 0.81720(12) 0.0479(3) Uani 1 1 d . . . . .
N34 N 1.01916(13) 0.03673(13) 0.70372(12) 0.0456(3) Uani 1 1 d . . . . .
O39 O 0.11919(14) 0.38222(15) 0.69400(15) 0.0722(4) Uani 1 1 d . . . . .
H39 H 0.065398 0.427579 0.731415 0.108 Uiso 1 1 calc R U . . .
N38 N 0.77637(14) 0.00859(13) 0.64321(12) 0.0472(3) Uani 1 1 d . . . . .
N2 N 0.56853(14) 0.59076(14) 0.54528(14) 0.0524(4) Uani 1 1 d . . . . .
O4 O 0.51318(16) 0.69119(14) 0.46940(15) 0.0775(4) Uani 1 1 d . . . . .
N6 N 0.71490(14) 0.26198(15) 0.69433(14) 0.0523(4) Uani 1 1 d . . . . .
H6A H 0.722383 0.195441 0.664720 0.063 Uiso 1 1 d R U . . .
H6B H 0.651534 0.266664 0.743808 0.063 Uiso 1 1 d R U . . .
N22 N 0.49837(16) 0.14061(17) 0.85829(14) 0.0601(4) Uani 1 1 d . . . . .
O3 O 0.51792(16) 0.56352(18) 0.63972(15) 0.0850(5) Uani 1 1 d . . . . .
N40 N 0.24878(16) 0.38614(17) 0.71377(15) 0.0597(4) Uani 1 1 d . . . . .
H40A H 0.297574 0.307817 0.749695 0.072 Uiso 1 1 d R U . . .
H40B H 0.285472 0.410770 0.648638 0.072 Uiso 1 1 d R U . . .
O24 O 0.39183(18) 0.12350(17) 0.83548(17) 0.0897(5) Uani 1 1 d . . . . .
C7 C 0.10757(15) 0.64108(15) 0.89736(12) 0.0413(3) Uani 1 1 d . . . . .
C25 C 1.01951(16) -0.06350(15) 0.65443(13) 0.0427(3) Uani 1 1 d . . . . .
C8 C -0.02397(15) 0.63377(15) 0.87499(12) 0.0422(3) Uani 1 1 d . . . . .
C26 C 0.89401(17) -0.07908(15) 0.62404(13) 0.0434(4) Uani 1 1 d . . . . .
C12 C 0.11912(17) 0.73284(16) 0.95927(14) 0.0464(4) Uani 1 1 d . . . . .
C9 C -0.13777(16) 0.72065(17) 0.91419(14) 0.0483(4) Uani 1 1 d . . . . .
C30 C 1.14140(17) -0.15515(16) 0.63313(14) 0.0473(4) Uani 1 1 d . . . . .
O23 O 0.60046(18) 0.0488(2) 0.8838(2) 0.1097(7) Uani 1 1 d . . . . .
C33 C 1.13540(18) 0.04674(18) 0.73211(16) 0.0539(4) Uani 1 1 d . . . . .
H33 H 1.134228 0.116093 0.765290 0.065 Uiso 1 1 calc R U . . .
C27 C 0.89778(19) -0.18644(16) 0.57546(14) 0.0510(4) Uani 1 1 d . . . . .
C14 C 0.35737(18) 0.65329(19) 0.94333(16) 0.0554(4) Uani 1 1 d . . . . .
H14 H 0.443482 0.653744 0.958466 0.066 Uiso 1 1 calc R U . . .
C13 C 0.24747(18) 0.73715(19) 0.98153(15) 0.0539(4) Uani 1 1 d . . . . .
H13 H 0.258066 0.796597 1.022021 0.065 Uiso 1 1 calc R U . . .
C28 C 1.0238(2) -0.27471(17) 0.55317(16) 0.0582(5) Uani 1 1 d . . . . .
H28 H 1.025143 -0.343328 0.518961 0.070 Uiso 1 1 calc R U . . .
C15 C 0.33735(17) 0.56763(19) 0.88153(15) 0.0532(4) Uani 1 1 d . . . . .
H15 H 0.412426 0.512023 0.854793 0.064 Uiso 1 1 calc R U . . .
C29 C 1.1396(2) -0.25986(17) 0.58085(15) 0.0558(4) Uani 1 1 d . . . . .
H29 H 1.220159 -0.318564 0.565866 0.067 Uiso 1 1 calc R U . . .
C11 C 0.00111(19) 0.81747(18) 0.99794(16) 0.0553(4) Uani 1 1 d . . . . .
H11 H 0.009501 0.877053 1.039225 0.066 Uiso 1 1 calc R U . . .
C35 C 0.66342(18) -0.01211(18) 0.61956(16) 0.0553(4) Uani 1 1 d . . . . .
H35 H 0.582991 0.047328 0.633861 0.066 Uiso 1 1 calc R U . . .
C17 C -0.15846(18) 0.54038(19) 0.79852(16) 0.0565(4) Uani 1 1 d . . . . .
H17 H -0.166712 0.478596 0.759667 0.068 Uiso 1 1 calc R U . . .
C37 C 0.7748(2) -0.20269(19) 0.55109(17) 0.0613(5) Uani 1 1 d . . . . .
H37 H 0.773772 -0.272073 0.518781 0.074 Uiso 1 1 calc R U . . .
C18 C -0.27571(19) 0.6234(2) 0.83369(18) 0.0617(5) Uani 1 1 d . . . . .
H18 H -0.359319 0.617100 0.817950 0.074 Uiso 1 1 calc R U . . .
C19 C -0.26489(18) 0.7130(2) 0.89117(17) 0.0598(5) Uani 1 1 d . . . . .
H19 H -0.341475 0.769345 0.915284 0.072 Uiso 1 1 calc R U . . .
C10 C -0.12119(18) 0.81270(19) 0.97593(16) 0.0577(4) Uani 1 1 d . . . . .
H10 H -0.196354 0.869861 1.001032 0.069 Uiso 1 1 calc R U . . .
C31 C 1.26167(18) -0.14021(18) 0.66515(16) 0.0570(4) Uani 1 1 d . . . . .
H31 H 1.343194 -0.198880 0.652000 0.068 Uiso 1 1 calc R U . . .
C32 C 1.25938(18) -0.0400(2) 0.71546(18) 0.0592(5) Uani 1 1 d . . . . .
H32 H 1.338475 -0.029700 0.738096 0.071 Uiso 1 1 calc R U . . .
C36 C 0.6572(2) -0.1174(2) 0.57454(17) 0.0621(5) Uani 1 1 d . . . . .
H36 H 0.575302 -0.128826 0.561006 0.075 Uiso 1 1 calc R U . . .
H40C H 0.243(3) 0.443(3) 0.759(2) 0.089(8) Uiso 1 1 d . . . . .
H6C H 0.695(2) 0.340(2) 0.631(2) 0.069(6) Uiso 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 N2 1.2608(19) . ?
O5 H5 0.8200 . ?
O5 N6 1.3962(19) . ?
N16 C7 1.362(2) . ?
N16 C15 1.324(2) . ?
O21 N22 1.258(2) . ?
N20 C8 1.360(2) . ?
N20 C17 1.320(2) . ?
N34 C25 1.358(2) . ?
N34 C33 1.322(2) . ?
O39 H39 0.8200 . ?
O39 N40 1.403(2) . ?
N38 C26 1.358(2) . ?
N38 C35 1.324(2) . ?
N2 O4 1.238(2) . ?
N2 O3 1.225(2) . ?
N6 H6A 0.8612 . ?
N6 H6B 0.8615 . ?
N6 H6C 0.96(2) . ?
N22 O24 1.238(2) . ?
N22 O23 1.213(2) . ?
N40 H40A 0.8658 . ?
N40 H40B 0.8655 . ?
N40 H40C 0.90(3) . ?
C7 C8 1.445(2) . ?
C7 C12 1.413(2) . ?
C25 C26 1.449(2) . ?
C25 C30 1.416(2) . ?
C8 C9 1.416(2) . ?
C26 C27 1.414(2) . ?
C12 C13 1.399(2) . ?
C12 C11 1.430(2) . ?
C9 C19 1.403(3) . ?
C9 C10 1.433(3) . ?
C30 C29 1.430(2) . ?
C30 C31 1.400(3) . ?
C33 H33 0.9300 . ?
C33 C32 1.392(3) . ?
C27 C28 1.433(3) . ?
C27 C37 1.404(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.369(3) . ?
C14 C15 1.387(3) . ?
C13 H13 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.337(3) . ?
C15 H15 0.9300 . ?
C29 H29 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.339(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.396(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.399(3) . ?
C37 H37 0.9300 . ?
C37 C36 1.362(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.355(3) . ?
C19 H19 0.9300 . ?
C10 H10 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.360(3) . ?
C32 H32 0.9300 . ?
C36 H36 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
N6 O5 H5 109.5 . . ?
C15 N16 C7 118.29(14) . . ?
C17 N20 C8 118.34(14) . . ?
C33 N34 C25 118.53(14) . . ?
N40 O39 H39 109.5 . . ?
C35 N38 C26 118.04(15) . . ?
O4 N2 O1 119.37(16) . . ?
O3 N2 O1 118.89(16) . . ?
O3 N2 O4 121.73(16) . . ?
O5 N6 H6A 109.7 . . ?
O5 N6 H6B 109.7 . . ?
O5 N6 H6C 110.2(13) . . ?
H6A N6 H6B 109.3 . . ?
H6A N6 H6C 106.5 . . ?
H6B N6 H6C 111.3 . . ?
O24 N22 O21 118.11(16) . . ?
O23 N22 O21 119.87(19) . . ?
O23 N22 O24 121.9(2) . . ?
O39 N40 H40A 109.7 . . ?
O39 N40 H40B 110.1 . . ?
O39 N40 H40C 108.6(17) . . ?
H40A N40 H40B 108.9 . . ?
H40A N40 H40C 108.6 . . ?
H40B N40 H40C 110.9 . . ?
N16 C7 C8 119.63(14) . . ?
N16 C7 C12 121.19(14) . . ?
C12 C7 C8 119.18(14) . . ?
N34 C25 C26 120.11(14) . . ?
N34 C25 C30 120.97(15) . . ?
C30 C25 C26 118.92(15) . . ?
N20 C8 C7 119.97(13) . . ?
N20 C8 C9 121.20(15) . . ?
C9 C8 C7 118.83(15) . . ?
N38 C26 C25 119.58(14) . . ?
N38 C26 C27 121.72(16) . . ?
C27 C26 C25 118.70(15) . . ?
C7 C12 C11 119.79(15) . . ?
C13 C12 C7 118.35(15) . . ?
C13 C12 C11 121.86(16) . . ?
C8 C9 C10 120.00(16) . . ?
C19 C9 C8 118.19(16) . . ?
C19 C9 C10 121.80(16) . . ?
C25 C30 C29 120.09(16) . . ?
C31 C30 C25 118.16(16) . . ?
C31 C30 C29 121.75(16) . . ?
N34 C33 H33 117.9 . . ?
N34 C33 C32 124.11(17) . . ?
C32 C33 H33 117.9 . . ?
C26 C27 C28 120.22(17) . . ?
C37 C27 C26 117.66(17) . . ?
C37 C27 C28 122.12(16) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.49(16) . . ?
C15 C14 H14 120.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.59(16) . . ?
C14 C13 H13 120.2 . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 120.97(16) . . ?
C29 C28 H28 119.5 . . ?
N16 C15 C14 124.07(16) . . ?
N16 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C30 C29 H29 119.5 . . ?
C28 C29 C30 121.07(16) . . ?
C28 C29 H29 119.5 . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.35(16) . . ?
C10 C11 H11 119.3 . . ?
N38 C35 H35 117.9 . . ?
N38 C35 C36 124.27(17) . . ?
C36 C35 H35 117.9 . . ?
N20 C17 H17 118.1 . . ?
N20 C17 C18 123.89(17) . . ?
C18 C17 H17 118.1 . . ?
C27 C37 H37 119.8 . . ?
C36 C37 C27 120.32(17) . . ?
C36 C37 H37 119.8 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.59(17) . . ?
C19 C18 H18 120.7 . . ?
C9 C19 H19 120.1 . . ?
C18 C19 C9 119.78(17) . . ?
C18 C19 H19 120.1 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.83(16) . . ?
C11 C10 H10 119.6 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.07(16) . . ?
C32 C31 H31 120.0 . . ?
C33 C32 H32 120.9 . . ?
C31 C32 C33 118.15(17) . . ?
C31 C32 H32 120.9 . . ?
C35 C36 H36 121.0 . . ?
C37 C36 C35 117.90(18) . . ?
C37 C36 H36 121.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
