# Supplementary Information (SI) for Materials Horizons.
# 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_js226j
_database_code_depnum_ccdc_archive 'CCDC 2542796'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2026-05-01 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_audit_creation_date             2026-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.07 svn.r39635298 for OlexSys, GUI svn.r7533)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2 H2 N5 O3), 2(H4 N)'
_chemical_formula_sum            'C4 H12 N12 O6'
_chemical_formula_weight         324.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H10N18O4
_chemical_oxdiff_usercomment     JS1743
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                   7.2916(6)
_cell_length_b                   7.5502(8)
_cell_length_c                   13.1587(7)
_cell_angle_alpha                94.215(7)
_cell_angle_beta                 94.320(6)
_cell_angle_gamma                116.254(10)
_cell_volume                     643.21(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2482
_cell_measurement_temperature    101(4)
_cell_measurement_theta_max      78.7010
_cell_measurement_theta_min      6.7830
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.125a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -2 0.0157
0 0 2 0.0034
-4 4 -2 0.0248
4 -4 0 0.0265
4 1 0 0.0216
-1 -3 3 0.0736
-4 3 -4 0.0216
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0350 0.0394 -2.0144 -0.0930 -0.1762 0.1275
-0.0350 -0.0394 2.0144 0.0930 0.1762 -0.1275
-3.5087 4.3339 -2.3197 0.1267 0.2678 0.9551
3.6523 -4.4633 -0.1804 -0.2419 -0.5091 -0.8260
3.7237 0.9027 0.3266 -0.8688 0.4141 -0.2716
-1.4052 -3.4578 2.8557 0.8151 -0.3895 -0.4289
-3.7208 3.1782 -4.2256 0.2303 -0.1085 0.9671

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9362
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.495
_diffrn_reflns_theta_min         3.393
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -43.00   0.50    1.00    --  -47.65 -44.00 151.00  152
  2  ω    -24.00  49.00   0.50    1.00    --   47.65 -44.00 151.00  146
  3  ω     37.00 118.00   0.50    1.00    --   47.65  44.00 -57.00  162
  4  ω   -127.00-101.00   0.50    4.00    --  -91.75 -44.00 151.00   52
  5  ω    -52.00 -26.00   0.50    4.00    --  -91.75  44.00 -57.00   52
  6  ω    141.00 171.00   0.50    4.00    --  113.25  44.00 -57.00   60
  7  ω    101.00 126.00   0.50    4.00    --  113.25  44.00 -57.00   50
  8  ω    -70.00 -13.00   0.50    1.00    --  -47.65  77.00   0.00  114
  9  ω    -27.00  15.00   0.50    1.00    --  -47.65  19.00-120.00   84
 10  ω    -51.00  20.00   0.50    1.00    --  -47.65  44.00 -57.00  142
 11  ω    -74.00 -24.00   0.50    1.00    --  -47.65 125.00  30.00  100
 12  ω      2.00  28.00   0.50    1.00    --   47.65 -19.00-180.00   52
 13  ω     51.00  84.00   0.50    1.00    --   47.65-125.00   0.00   66
 14  ω    -72.00 -24.00   0.50    4.00    --  -91.75 125.00   0.00   96
 15  ω   -157.00-123.00   0.50    4.00    --  -91.75 -77.00 -60.00   68
 16  ω     43.00  68.00   0.50    4.00    --  113.25 -61.00  90.00   50
 17  ω     42.00  69.00   0.50    4.00    --  113.25 -61.00-120.00   54
 18  ω    147.00 173.00   0.50    4.00    --  113.25  15.00  30.00   52
 19  ω     63.00 108.00   0.50    4.00    --  113.25-125.00  30.00   90
 20  ω    106.00 135.00   0.50    4.00    --  113.25  45.00  60.00   58
 21  ω    140.00 170.00   0.50    4.00    --  113.25  45.00  60.00   60
 22  ω     47.00 102.00   0.50    4.00    --  113.25-125.00 -90.00  110
 23  ω     42.00  68.00   0.50    4.00    --  113.25 -94.00-180.00   52
 24  ω     45.00  70.00   0.50    4.00    --  113.25 -94.00  90.00   50
 25  ω     42.00  68.00   0.50    4.00    --  113.25 -61.00 150.00   52
 26  ω    108.00 134.00   0.50    4.00    --  113.25  15.00  30.00   52
 27  ω     72.00 103.00   0.50    4.00    --  113.25 -94.00  90.00   62
 28  ω     77.00 103.00   0.50    4.00    --  113.25 -94.00 120.00   52
 29  ω     76.00 102.00   0.50    4.00    --  113.25 -94.00-180.00   52
 30  ω     62.00 104.00   0.50    4.00    --  113.25 -94.00 -60.00   84
 31  ω    114.00 177.00   0.50    4.00    --  113.25  61.00  90.00  126
 32  ω    131.00 157.00   0.50    4.00    --  113.25 125.00 150.00   52
 33  ω    113.00 173.00   0.50    4.00    --  113.25  61.00-180.00  120
 34  ω    119.00 172.00   0.50    4.00    --  113.25  77.00-150.00  106
 35  ω     61.00 102.00   0.50    4.00    --  113.25 -94.00  60.00   82
 36  ω     45.00 101.00   0.50    4.00    --  113.25-125.00 -60.00  112
 37  ω     43.00  69.00   0.50    4.00    --  113.25 -94.00 150.00   52
 38  ω     42.00  67.00   0.50    4.00    --  113.25 -61.00 -90.00   50
 39  ω     49.00  75.00   0.50    4.00    --  113.25 -94.00-150.00   52
 40  ω    120.00 173.00   0.50    4.00    --  113.25  77.00-120.00  106
 41  ω    114.00 155.00   0.50    4.00    --  113.25  61.00 -30.00   82
 42  ω     78.00 103.00   0.50    4.00    --  113.25 -94.00-150.00   50
 43  ω     62.00 104.00   0.50    4.00    --  113.25 -94.00   0.00   84
 44  ω    120.00 155.00   0.50    4.00    --  113.25 125.00  90.00   70
 45  ω     44.00  69.00   0.50    4.00    --  113.25 -61.00 120.00   50
 46  ω     76.00 101.00   0.50    4.00    --  113.25 -94.00 -90.00   50
 47  ω     79.00 104.00   0.50    4.00    --  113.25 -94.00 150.00   50
 48  ω    119.00 168.00   0.50    4.00    --  113.25  77.00 150.00   98
 49  ω    114.00 140.00   0.50    4.00    --  113.25  61.00-150.00   52
 50  ω     42.00  67.00   0.50    4.00    --  113.25 -61.00-180.00   50
 51  ω     42.00 103.00   0.50    4.00    --  113.25 -94.00  30.00  122
 52  ω     59.00  85.00   0.50    4.00    --  113.25-125.00   0.00   52
 53  ω    117.00 162.00   0.50    4.00    --  113.25  77.00 -90.00   90
 54  ω     83.00 108.00   0.50    4.00    --  113.25-125.00 150.00   50
 55  ω     43.00  68.00   0.50    4.00    --  113.25 -61.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2082653630
_diffrn_orient_matrix_UB_12      -0.1178442505
_diffrn_orient_matrix_UB_13      0.0402500970
_diffrn_orient_matrix_UB_21      0.0637491524
_diffrn_orient_matrix_UB_22      0.1625296130
_diffrn_orient_matrix_UB_23      0.0917778380
_diffrn_orient_matrix_UB_31      -0.0942300410
_diffrn_orient_matrix_UB_32      0.1104910869
_diffrn_orient_matrix_UB_33      -0.0627793614
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name JS226J.par
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1344
_reflns_number_total             2719
_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 1.171.44.125a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.142a 64-bit (release 06-02-2026))'
_computing_data_reduction        'CrysAlisPro 1.171.44.125a (Rigaku OD, 2025)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0745
_refine_ls_restrained_S_all      1.110
_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)+(0.1151P)²+1.0301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2341
_refine_ls_wR_factor_ref         0.2640
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H,H,H) groups
2.a Riding coordinates:
 N1C(H1CA,H1CB,H1CC,H1CD), N2C(H2CA,H2CB,H2CC,H2CD)
2.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N2A(H2A), N1B(H1B), N2B(H2B)
;
_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
O1A O 0.2717(5) 0.0152(4) 0.2100(2) 0.0275(7) Uani 1 1 d . . . . .
O2A O 0.8239(5) 0.5739(5) 0.0873(2) 0.0277(7) Uani 1 1 d . . . . .
O3A O 0.8980(5) 0.6507(5) -0.0655(2) 0.0304(7) Uani 1 1 d . . . . .
N1A N 0.4933(5) 0.2414(5) 0.1087(2) 0.0239(7) Uani 1 1 d . . . . .
H1A H 0.583843 0.331726 0.156576 0.029 Uiso 1 1 calc R U . . .
N2A N 0.2312(5) -0.0188(5) 0.0292(2) 0.0237(7) Uani 1 1 d . . . . .
H2A H 0.116886 -0.131196 0.017718 0.028 Uiso 1 1 calc R U . . .
N3A N 0.3345(6) 0.0846(5) -0.0477(2) 0.0261(8) Uani 1 1 d . . . . .
N4A N 0.6235(6) 0.3760(5) -0.0554(3) 0.0252(7) Uani 1 1 d . . . . .
N5A N 0.7809(5) 0.5328(5) -0.0093(2) 0.0227(7) Uani 1 1 d . . . . .
C1A C 0.3246(6) 0.0713(6) 0.1231(3) 0.0226(8) Uani 1 1 d . . . . .
C2A C 0.4930(6) 0.2427(6) 0.0062(3) 0.0241(9) Uani 1 1 d . . . . .
O1B O 0.7285(5) 0.4844(4) 0.2898(2) 0.0274(7) Uani 1 1 d . . . . .
O2B O 0.1769(5) -0.0750(5) 0.4109(2) 0.0273(7) Uani 1 1 d . . . . .
O3B O 0.1028(5) -0.1514(4) 0.56616(19) 0.0257(7) Uani 1 1 d . . . . .
N1B N 0.5063(5) 0.2586(5) 0.3924(3) 0.0242(7) Uani 1 1 d . . . . .
H1B H 0.413640 0.166928 0.345673 0.029 Uiso 1 1 calc R U . . .
N2B N 0.7682(6) 0.5181(5) 0.4675(3) 0.0249(8) Uani 1 1 d . . . . .
H2B H 0.881733 0.631162 0.479056 0.030 Uiso 1 1 calc R U . . .
N3B N 0.6657(5) 0.4132(5) 0.5431(2) 0.0221(7) Uani 1 1 d . . . . .
N4B N 0.3760(6) 0.1250(5) 0.5544(2) 0.0248(8) Uani 1 1 d . . . . .
N5B N 0.2193(5) -0.0327(5) 0.5056(3) 0.0242(8) Uani 1 1 d . . . . .
C1B C 0.6734(6) 0.4264(6) 0.3734(3) 0.0255(9) Uani 1 1 d . . . . .
C2B C 0.5081(6) 0.2582(6) 0.4981(3) 0.0212(8) Uani 1 1 d . . . . .
N1C N 0.1493(6) 0.1025(6) -0.2481(2) 0.0287(8) Uani 1 1 d . . . . .
H1CA H 0.218710 0.110075 -0.187093 0.034 Uiso 1 1 d R U . . .
H1CB H 0.186030 0.226376 -0.264471 0.034 Uiso 1 1 d R U . . .
H1CC H 0.158210 0.011036 -0.292592 0.034 Uiso 1 1 d R U . . .
H1CD H 0.012200 0.054746 -0.248193 0.034 Uiso 1 1 d R U . . .
N2C N 1.1478(6) 0.6014(5) 0.2510(2) 0.0272(8) Uani 1 1 d . . . . .
H2CA H 1.015590 0.564458 0.260827 0.033 Uiso 1 1 d R U . . .
H2CB H 1.148040 0.529566 0.193358 0.033 Uiso 1 1 d R U . . .
H2CC H 1.215073 0.581905 0.305907 0.033 Uiso 1 1 d R U . . .
H2CD H 1.198896 0.730379 0.241006 0.033 Uiso 1 1 d 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
O1A C1A 1.276(5) . ?
O2A N5A 1.267(4) . ?
O3A N5A 1.260(5) . ?
N1A H1A 0.8800 . ?
N1A C1A 1.368(5) . ?
N1A C2A 1.349(5) . ?
N2A H2A 0.8800 . ?
N2A N3A 1.382(5) . ?
N2A C1A 1.339(5) . ?
N3A C2A 1.340(5) . ?
N4A N5A 1.294(5) . ?
N4A C2A 1.402(6) . ?
O1B C1B 1.242(5) . ?
O2B N5B 1.244(4) . ?
O3B N5B 1.301(4) . ?
N1B H1B 0.8800 . ?
N1B C1B 1.371(5) . ?
N1B C2B 1.390(5) . ?
N2B H2B 0.8800 . ?
N2B N3B 1.371(5) . ?
N2B C1B 1.347(5) . ?
N3B C2B 1.284(5) . ?
N4B N5B 1.307(5) . ?
N4B C2B 1.359(5) . ?
N1C H1CA 0.9000 . ?
N1C H1CB 0.9000 . ?
N1C H1CC 0.9000 . ?
N1C H1CD 0.9000 . ?
N2C H2CA 0.9000 . ?
N2C H2CB 0.9000 . ?
N2C H2CC 0.9001 . ?
N2C H2CD 0.9000 . ?

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
C1A N1A H1A 126.9 . . ?
C2A N1A H1A 126.9 . . ?
C2A N1A C1A 106.2(3) . . ?
N3A N2A H2A 123.8 . . ?
C1A N2A H2A 123.8 . . ?
C1A N2A N3A 112.4(3) . . ?
C2A N3A N2A 102.0(3) . . ?
N5A N4A C2A 117.4(3) . . ?
O2A N5A N4A 124.5(3) . . ?
O3A N5A O2A 118.7(3) . . ?
O3A N5A N4A 116.8(3) . . ?
O1A C1A N1A 125.4(3) . . ?
O1A C1A N2A 128.5(4) . . ?
N2A C1A N1A 106.1(3) . . ?
N1A C2A N4A 133.2(4) . . ?
N3A C2A N1A 113.3(4) . . ?
N3A C2A N4A 113.5(3) . . ?
C1B N1B H1B 125.8 . . ?
C1B N1B C2B 108.3(3) . . ?
C2B N1B H1B 125.8 . . ?
N3B N2B H2B 124.2 . . ?
C1B N2B H2B 124.2 . . ?
C1B N2B N3B 111.6(3) . . ?
C2B N3B N2B 106.8(3) . . ?
N5B N4B C2B 118.3(3) . . ?
O2B N5B O3B 120.1(3) . . ?
O2B N5B N4B 126.3(3) . . ?
O3B N5B N4B 113.6(3) . . ?
O1B C1B N1B 129.2(4) . . ?
O1B C1B N2B 126.8(4) . . ?
N2B C1B N1B 104.0(3) . . ?
N3B C2B N1B 109.3(3) . . ?
N3B C2B N4B 120.2(3) . . ?
N4B C2B N1B 130.5(4) . . ?
H1CA N1C H1CB 108.9 . . ?
H1CA N1C H1CC 108.9 . . ?
H1CA N1C H1CD 114.8 . . ?
H1CB N1C H1CC 120.0 . . ?
H1CB N1C H1CD 102.1 . . ?
H1CC N1C H1CD 102.1 . . ?
H2CA N2C H2CB 107.6 . . ?
H2CA N2C H2CC 110.0 . . ?
H2CA N2C H2CD 105.1 . . ?
H2CB N2C H2CC 111.8 . . ?
H2CB N2C H2CD 109.4 . . ?
H2CC N2C H2CD 112.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O2A 0.88 2.21 2.654(5) 110.7 . yes
N1A H1A O1B 0.88 1.97 2.819(4) 163.0 . yes
N2A H2A O3A 0.88 1.90 2.721(5) 155.0 1_445 yes
N1B H1B O1A 0.88 1.99 2.831(4) 160.7 . yes
N1B H1B O2B 0.88 2.17 2.645(5) 113.2 . yes
N2B H2B O3B 0.88 1.93 2.743(5) 153.7 1_665 yes
N1C H1CA N3A 0.90 2.02 2.911(4) 170.6 . yes
N1C H1CB O1B 0.90 2.05 2.948(5) 175.5 2_665 yes
N1C H1CC O3B 0.90 2.06 2.894(4) 154.0 1_554 yes
N1C H1CD O1A 0.90 2.01 2.889(5) 164.7 2 yes
N1C H1CD O2B 0.90 2.51 3.003(4) 115.0 2 yes
N2C H2CA O1B 0.90 1.98 2.881(5) 177.2 . yes
N2C H2CB O3A 0.90 1.99 2.885(5) 171.2 2_765 yes
N2C H2CC N3B 0.90 2.10 2.970(4) 162.7 2_766 yes
N2C H2CD O1A 0.90 2.06 2.949(4) 171.5 1_665 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2A N3A C2A N1A 0.4(5) . . . . ?
N2A N3A C2A N4A -179.2(3) . . . . ?
N3A N2A C1A O1A -179.2(4) . . . . ?
N3A N2A C1A N1A 1.0(5) . . . . ?
N5A N4A C2A N1A 0.7(7) . . . . ?
N5A N4A C2A N3A -179.9(3) . . . . ?
C1A N1A C2A N3A 0.2(5) . . . . ?
C1A N1A C2A N4A 179.6(4) . . . . ?
C1A N2A N3A C2A -0.8(4) . . . . ?
C2A N1A C1A O1A 179.5(4) . . . . ?
C2A N1A C1A N2A -0.7(4) . . . . ?
C2A N4A N5A O2A -0.4(6) . . . . ?
C2A N4A N5A O3A 179.5(3) . . . . ?
N2B N3B C2B N1B 0.5(4) . . . . ?
N2B N3B C2B N4B -179.9(3) . . . . ?
N3B N2B C1B O1B 179.9(4) . . . . ?
N3B N2B C1B N1B 0.0(4) . . . . ?
N5B N4B C2B N1B 0.7(7) . . . . ?
N5B N4B C2B N3B -178.9(3) . . . . ?
C1B N1B C2B N3B -0.5(5) . . . . ?
C1B N1B C2B N4B 179.9(4) . . . . ?
C1B N2B N3B C2B -0.3(4) . . . . ?
C2B N1B C1B O1B -179.6(4) . . . . ?
C2B N1B C1B N2B 0.3(4) . . . . ?
C2B N4B N5B O2B -0.1(6) . . . . ?
C2B N4B N5B O3B 179.6(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JS1743
_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 2.035
_oxdiff_exptl_absorpt_empirical_full_min 0.561
####################################################################### 
# 
# 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_js226e
_database_code_depnum_ccdc_archive 'CCDC 2542795'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2026-03-31 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_audit_creation_date             2026-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N6 O3, 2(H4 N)'
_chemical_formula_sum            'C2 H8 N8 O3'
_chemical_formula_weight         192.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C2 H8 N8 O3 '
_chemical_oxdiff_usercomment     JS1741
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.1181(5)
_cell_length_b                   8.0305(2)
_cell_length_c                   15.6693(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.049(4)
_cell_angle_gamma                90
_cell_volume                     1495.42(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3178
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6190
_cell_measurement_theta_min      6.2180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.142a (Rigaku Oxford Diffraction, 2026)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0417
0 -1 0 0.0644
0 0 1 0.0138
0 0 -1 0.0087
-1 0 1 0.0108
1 0 -1 0.0134
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.022
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0009 1.0001 0.0007 -0.0833 -0.1727 -0.0066
0.0009 -1.0001 -0.0007 0.0833 0.1727 0.0066
-0.0006 -0.0005 1.0007 -0.0267 0.0090 0.1047
0.0006 0.0005 -1.0007 0.0267 -0.0090 -0.1047
-1.0001 -0.0001 1.0010 0.0886 -0.0460 0.0820
1.0001 0.0001 -1.0010 -0.0886 0.0460 -0.0820

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5688
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.950
_diffrn_reflns_theta_min         6.235
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -67.00   0.50    1.08    --  -47.65-138.00  33.00  106
  2  ω    -91.00 -57.00   0.50    1.08    --  -47.65 138.00  94.00   68
  3  ω   -114.00 -72.00   0.50    1.08    --  -47.65-130.00-151.00   84
  4  ω     61.00 100.00   0.50    1.08    --   47.65-138.00  33.00   78
  5  ω   -140.00-115.00   0.50    4.33    --  -91.75-130.00-151.00   50
  6  ω   -111.00 -76.00   0.50    4.33    --  -91.75-138.00  33.00   70
  7  ω     86.00 113.00   0.50    4.33    --  113.25-138.00  33.00   54
  8  ω     42.00 110.00   0.50    4.33    --  113.25-130.00-151.00  136
  9  ω    112.00 137.00   0.50    4.33    --  113.25 130.00 -80.00   50
 10  ω     44.00  83.00   0.50    4.33    --  113.25-138.00  33.00   78
 11  ω    -29.00  28.00   0.50    1.08    --  -47.65  19.00 -60.00  114
 12  ω    -25.00  27.00   0.50    1.08    --  -47.65  19.00-120.00  104
 13  ω     -1.00  24.00   0.50    1.08    --   47.65 -19.00 -90.00   50
 14  ω     44.00  69.00   0.50    1.08    --   47.65-130.00-151.00   50
 15  ω    -48.00 -22.00   0.50    4.33    --  -91.75  45.00  30.00   52
 16  ω   -163.00-118.00   0.50    4.33    --  -91.75 -61.00 -60.00   90
 17  ω    -53.00 -28.00   0.50    4.33    --  -91.75  45.00 -30.00   50
 18  ω     43.00  77.00   0.50    4.33    --  113.25-125.00 150.00   68
 19  ω     43.00  70.00   0.50    4.33    --  113.25 -94.00 -90.00   54
 20  ω    101.00 158.00   0.50    4.33    --  113.25  30.00  90.00  114
 21  ω     55.00 103.00   0.50    4.33    --  113.25 -94.00 -60.00   96
 22  ω     76.00 104.00   0.50    4.33    --  113.25 -94.00 -90.00   56
 23  ω     59.00  85.00   0.50    4.33    --  113.25-125.00  90.00   52
 24  ω    129.00 170.00   0.50    4.33    --  113.25  77.00-180.00   82
 25  ω     74.00 104.00   0.50    4.33    --  113.25 -94.00-180.00   60
 26  ω     98.00 151.00   0.50    4.33    --  113.25 125.00 120.00  106
 27  ω    100.00 160.00   0.50    4.33    --  113.25 125.00-120.00  120
 28  ω     44.00 104.00   0.50    4.33    --  113.25 -94.00-120.00  120
 29  ω     76.00 103.00   0.50    4.33    --  113.25 -94.00-150.00   54
 30  ω     42.00  68.00   0.50    4.33    --  113.25 -61.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1153480000
_diffrn_orient_matrix_UB_12      -0.0833657000
_diffrn_orient_matrix_UB_13      -0.0267843000
_diffrn_orient_matrix_UB_21      0.0549056000
_diffrn_orient_matrix_UB_22      -0.1726788000
_diffrn_orient_matrix_UB_23      0.0088867000
_diffrn_orient_matrix_UB_31      0.0227514000
_diffrn_orient_matrix_UB_32      -0.0066847000
_diffrn_orient_matrix_UB_33      0.1046775000
_diffrn_oxdiff_digest_hkl        
;
43ac2842d3905bc8f3e3224c29598c275461a4
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name JS226E.par
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1398
_reflns_number_total             1591
_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 1.171.44.142a (Rigaku OD, 2026)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.142a 64-bit (release 06-02-2026))'
_computing_data_reduction        'CrysAlisPro 1.171.44.142a (Rigaku OD, 2026)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.063
_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)+(0.0544P)²+0.3754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.13238(7) 0.96367(11) 0.45305(6) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.12082(7) 1.44513(11) 0.05438(6) 0.0200(2) Uani 1 1 d . . . . .
O3 O 0.08019(7) 1.49116(11) 0.17347(6) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.13022(8) 1.00745(12) 0.23252(7) 0.0173(2) Uani 1 1 d . . . . .
N2 N 0.13134(8) 0.93466(13) 0.30820(7) 0.0176(2) Uani 1 1 d . . . . .
N3 N 0.15730(9) 1.26945(13) 0.30750(6) 0.0197(2) Uani 1 1 d . . . . .
N4 N 0.15777(9) 1.19927(13) 0.38390(7) 0.0203(2) Uani 1 1 d . . . . .
N5 N 0.13602(8) 1.23441(12) 0.14748(6) 0.0176(2) Uani 1 1 d . . . . .
N6 N 0.11223(8) 1.39202(12) 0.12736(6) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.13759(9) 1.17527(14) 0.23162(8) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.13907(9) 1.03200(14) 0.38266(8) 0.0165(2) Uani 1 1 d . . . . .
N8 N 0.15959(9) 1.59370(13) 0.38090(7) 0.0174(2) Uani 1 1 d . . . . .
H8A H 0.1503(14) 1.695(2) 0.3523(11) 0.026(4) Uiso 1 1 d . . . . .
H8B H 0.1595(14) 1.515(2) 0.3407(12) 0.025(4) Uiso 1 1 d . . . . .
H8C H 0.2230(16) 1.584(2) 0.4315(13) 0.028(4) Uiso 1 1 d . . . . .
H8D H 0.1054(18) 1.577(3) 0.3952(13) 0.040(5) Uiso 1 1 d . . . . .
N7 N 0.07037(9) 0.80436(13) 0.05824(7) 0.0178(2) Uani 1 1 d . . . . .
H7A H 0.0995(14) 0.846(2) 0.1155(12) 0.025(4) Uiso 1 1 d . . . . .
H7B H 0.0949(14) 0.863(2) 0.0225(12) 0.028(4) Uiso 1 1 d . . . . .
H7C H -0.0036(18) 0.824(3) 0.0358(13) 0.040(5) Uiso 1 1 d . . . . .
H7D H 0.0884(16) 0.695(3) 0.0592(13) 0.038(5) 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 1.2677(14) . ?
O2 N6 1.2694(12) . ?
O3 N6 1.2608(13) . ?
N1 N2 1.3166(13) . ?
N1 C1 1.3516(15) . ?
N2 C2 1.3720(15) . ?
N3 N4 1.3208(13) . ?
N3 C1 1.3387(15) . ?
N4 C2 1.3641(15) . ?
N5 N6 1.3097(14) . ?
N5 C1 1.3932(14) . ?
N8 H8A 0.914(18) . ?
N8 H8B 0.894(18) . ?
N8 H8C 0.88(2) . ?
N8 H8D 0.84(2) . ?
N7 H7A 0.877(18) . ?
N7 H7B 0.890(18) . ?
N7 H7C 0.90(2) . ?
N7 H7D 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 118.58(9) . . ?
N1 N2 C2 118.79(10) . . ?
N4 N3 C1 119.27(10) . . ?
N3 N4 C2 118.39(9) . . ?
N6 N5 C1 117.63(9) . . ?
O2 N6 N5 116.01(9) . . ?
O3 N6 O2 118.84(9) . . ?
O3 N6 N5 125.14(9) . . ?
N1 C1 N5 112.16(9) . . ?
N3 C1 N1 122.81(10) . . ?
N3 C1 N5 124.59(11) . . ?
O1 C2 N2 119.06(10) . . ?
O1 C2 N4 119.48(10) . . ?
N4 C2 N2 121.41(10) . . ?
H8A N8 H8B 109.1(14) . . ?
H8A N8 H8C 113.4(16) . . ?
H8A N8 H8D 108.8(17) . . ?
H8B N8 H8C 107.2(16) . . ?
H8B N8 H8D 109.0(18) . . ?
H8C N8 H8D 109.3(17) . . ?
H7A N7 H7B 109.1(16) . . ?
H7A N7 H7C 105.5(16) . . ?
H7A N7 H7D 110.5(16) . . ?
H7B N7 H7C 106.2(16) . . ?
H7B N7 H7D 111.1(16) . . ?
H7C N7 H7D 114.1(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8A N2 0.914(18) 2.022(19) 2.9282(14) 171.0(15) 1_565 yes
N8 H8B O3 0.894(18) 2.382(17) 3.0758(13) 134.5(14) . yes
N8 H8B N3 0.894(18) 2.034(18) 2.8417(15) 149.7(15) . yes
N8 H8C O1 0.88(2) 2.03(2) 2.9012(14) 173.9(17) 7_576 yes
N8 H8D O2 0.84(2) 2.422(19) 2.9859(13) 125.0(16) 6_586 yes
N8 H8D O3 0.84(2) 2.31(2) 3.0047(14) 139.9(17) 2 yes
N7 H7A N1 0.877(18) 2.143(18) 2.9864(14) 161.2(16) . yes
N7 H7B O1 0.890(18) 1.954(19) 2.8256(13) 166.2(16) 6_575 yes
N7 H7C O1 0.90(2) 2.10(2) 2.8886(13) 147.0(17) 2 yes
N7 H7D O2 0.90(2) 2.06(2) 2.9660(14) 176.6(18) 1_545 yes
N7 H7D O3 0.90(2) 2.46(2) 3.0670(13) 124.3(14) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 O1 175.19(10) . . . . ?
N1 N2 C2 N4 -7.19(16) . . . . ?
N2 N1 C1 N3 6.92(16) . . . . ?
N2 N1 C1 N5 179.66(9) . . . . ?
N3 N4 C2 O1 -175.77(10) . . . . ?
N3 N4 C2 N2 6.62(16) . . . . ?
N4 N3 C1 N1 -7.52(17) . . . . ?
N4 N3 C1 N5 -179.35(10) . . . . ?
N6 N5 C1 N1 161.99(10) . . . . ?
N6 N5 C1 N3 -25.42(16) . . . . ?
C1 N1 N2 C2 0.48(15) . . . . ?
C1 N3 N4 C2 0.64(16) . . . . ?
C1 N5 N6 O2 174.24(9) . . . . ?
C1 N5 N6 O3 -7.11(16) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JS1741
_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 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.830
####################################################################### 
# 
# 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_js825a
_database_code_depnum_ccdc_archive 'CCDC 2542797'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2026-03-31 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_audit_creation_date             2025-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N6 O3, 2(C3 H7 N8)'
_chemical_formula_sum            'C8 H14 N22 O3'
_chemical_formula_weight         466.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4N6O5H2
_chemical_oxdiff_usercomment     JS1507
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                   9.0884(4)
_cell_length_b                   10.2064(5)
_cell_length_c                   10.7479(5)
_cell_angle_alpha                73.853(4)
_cell_angle_beta                 66.266(5)
_cell_angle_gamma                75.743(4)
_cell_volume                     866.36(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7056
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5970
_cell_measurement_theta_min      4.5520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.257
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0558
0 -1 -1 0.0653
-4 -1 -7 0.0667
-4 2 -5 0.0520
4 -2 4 0.0435
5 5 5 0.0195
-1 -1 -1 0.0042
6 2 1 0.0512
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0009 0.9991 0.9992 0.1352 -0.1489 -0.0064
-0.0009 -0.9991 -0.9992 -0.1352 0.1489 0.0064
-3.7430 -1.0255 -6.6146 -0.3368 0.3926 -0.8558
-4.2044 1.9787 -4.5155 0.0165 -0.0215 -0.9996
4.2030 -1.9963 4.4969 -0.0188 0.0242 0.9995
4.8946 4.5416 4.5658 -0.1129 -0.8624 0.4935
-0.9999 -0.9988 -0.9987 0.0141 0.1867 -0.0999
5.7341 1.7417 1.2982 -0.6811 -0.4689 0.5623

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10630
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.200
_diffrn_reflns_theta_min         4.564
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  18.00   0.50    0.15    --  -47.65  37.00 120.00  126
  2  ω    -67.00 -19.00   0.50    0.15    --  -47.65  75.00 -26.00   96
  3  ω    -14.00  24.00   0.50    0.15    --  -47.65  75.00 -26.00   76
  4  ω    -45.00  23.00   0.50    0.15    --  -47.65  37.00-120.00  136
  5  ω    -26.00   0.00   0.50    0.15    --  -47.65  19.00-120.00   52
  6  ω    -29.00  28.00   0.50    0.15    --  -47.65  19.00   0.00  114
  7  ω     50.00 108.00   0.50    0.61    --  113.25-125.00-150.00  116
  8  ω     65.00 103.00   0.50    0.61    --  113.25 -94.00-180.00   76
  9  ω     58.00 103.00   0.50    0.61    --  113.25 -94.00-120.00   90
 10  ω     74.00  99.00   0.50    0.61    --  113.25 -94.00-150.00   50
 11  ω     58.00 101.00   0.50    0.61    --  113.25 -94.00 -60.00   86
 12  ω     45.00  96.00   0.50    0.61    --  113.25 -94.00 -90.00  102
 13  ω     52.00 102.00   0.50    0.61    --  113.25 -94.00 -30.00  100
 14  ω     69.00 101.00   0.50    0.61    --  113.25 -94.00   0.00   64
 15  ω     58.00  97.00   0.50    0.61    --  113.25 -94.00  60.00   78
 16  ω     42.00 103.00   0.50    0.61    --  113.25 -94.00 120.00  122
 17  ω     45.00 100.00   0.50    0.61    --  113.25 -94.00  90.00  110
 18  ω     76.00 102.00   0.50    0.61    --  113.25 -94.00  30.00   52
 19  ω     48.00  77.00   0.50    0.61    --  113.25 -77.00 -30.00   58
 20  ω     43.00  69.00   0.50    0.61    --  113.25 -61.00   0.00   52
 21  ω     42.00  67.00   0.50    0.61    --  113.25 -61.00  60.00   50
 22  ω     43.00  68.00   0.50    0.61    --  113.25 -61.00-120.00   50
 23  ω     46.00  71.00   0.50    0.61    --  113.25 -75.00-153.00   50
 24  ω     43.00  68.00   0.50    0.61    --  113.25 -61.00-180.00   50
 25  ω    153.00 178.00   0.50    0.61    --  113.25  30.00-120.00   50
 26  ω    143.00 173.00   0.50    0.61    --  113.25  75.00 -26.00   60
 27  ω    107.00 133.00   0.50    0.61    --  113.25  75.00 -26.00   52
 28  ω    101.00 137.00   0.50    0.61    --  113.25  45.00  30.00   72
 29  ω    141.00 175.00   0.50    0.61    --  113.25  45.00  30.00   68
 30  ω    147.00 177.00   0.50    0.61    --  113.25  45.00  60.00   60
 31  ω    117.00 178.00   0.50    0.61    --  113.25  77.00  90.00  122
 32  ω    102.00 177.00   0.50    0.61    --  113.25  45.00 150.00  150
 33  ω    101.00 134.00   0.50    0.61    --  113.25  45.00  60.00   66
 34  ω    141.00 171.00   0.50    0.61    --  113.25  30.00 -90.00   60
 35  ω    103.00 131.00   0.50    0.61    --  113.25  45.00 -60.00   56
 36  ω    114.00 139.00   0.50    0.61    --  113.25  30.00-120.00   50
 37  ω    108.00 134.00   0.50    0.61    --  113.25  30.00 -90.00   52
 38  ω      4.00  30.00   0.50    0.15    --   47.65 -75.00-153.00   52
 39  ω     39.00  70.00   0.50    0.15    --   47.65 -75.00-153.00   62
 40  ω    101.00 151.00   0.50    0.61    --  113.25 125.00 -90.00  100
 41  ω    104.00 129.00   0.50    0.61    --  113.25 125.00 150.00   50
 42  ω    -82.00 -57.00   0.50    0.61    --  -91.75  75.00 -26.00   50
 43  ω    -48.00 -23.00   0.50    0.61    --  -91.75  45.00-180.00   50
 44  ω    -51.00 -24.00   0.50    0.61    --  -91.75  45.00 -30.00   54
 45  ω    -53.00 -27.00   0.50    0.61    --  -91.75  45.00 120.00   52
 46  ω    -53.00 -28.00   0.50    0.61    --  -91.75  45.00 150.00   50
 47  ω    -51.00 -20.00   0.50    0.15    --  -47.65 125.00  90.00   62
 48  ω   -163.00-127.00   0.50    0.61    --  -91.75 -61.00  60.00   72
 49  ω   -137.00 -82.00   0.50    0.61    --  -91.75 -75.00-153.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1494515000
_diffrn_orient_matrix_UB_12      -0.0000049000
_diffrn_orient_matrix_UB_13      0.1354910000
_diffrn_orient_matrix_UB_21      -0.0378939000
_diffrn_orient_matrix_UB_22      -0.1314077000
_diffrn_orient_matrix_UB_23      -0.0175396000
_diffrn_orient_matrix_UB_31      0.1064668000
_diffrn_orient_matrix_UB_32      -0.0895277000
_diffrn_orient_matrix_UB_33      0.0830157000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3306
_reflns_number_total             3659
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.019
_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)+(0.0440P)²+0.4531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.69210(13) 0.58872(10) 0.70916(11) 0.0223(2) Uani 1 1 d . . . . .
O2 O 1.06483(12) 0.79508(10) 0.93915(10) 0.0224(2) Uani 1 1 d . . . . .
O3 O 1.01098(14) 0.75036(10) 1.16258(11) 0.0238(2) Uani 1 1 d . . . . .
N1 N 0.83025(14) 0.75160(11) 0.87488(12) 0.0150(2) Uani 1 1 d . . . . .
N2 N 0.77870(14) 0.73298(11) 0.78232(12) 0.0156(2) Uani 1 1 d . . . . .
N3 N 0.72518(13) 0.50897(11) 0.91840(12) 0.0155(2) Uani 1 1 d . . . . .
N4 N 0.77812(13) 0.52838(11) 1.00725(12) 0.0152(2) Uani 1 1 d . . . . .
N5 N 0.87819(13) 0.65724(11) 1.08934(11) 0.0152(2) Uani 1 1 d . . . . .
N6 N 0.98553(14) 0.73738(11) 1.05992(12) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.83555(15) 0.64821(13) 0.98122(13) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.73253(16) 0.61035(13) 0.79977(14) 0.0151(3) Uani 1 1 d . . . . .
N7 N 0.80591(14) 0.99548(11) 0.62089(11) 0.0148(2) Uani 1 1 d . . . . .
N8 N 0.76540(13) 1.06638(11) 0.50360(11) 0.0148(2) Uani 1 1 d . . . . .
N9 N 0.81870(13) 1.30719(11) 0.38863(11) 0.0138(2) Uani 1 1 d . . . . .
N10 N 0.93188(13) 1.32038(11) 0.53907(12) 0.0146(2) Uani 1 1 d . . . . .
N11 N 0.88251(13) 1.19166(11) 0.56758(11) 0.0133(2) Uani 1 1 d . . . . .
N12 N 0.71531(15) 1.35226(12) 0.31183(13) 0.0169(2) Uani 1 1 d . . . . .
N13 N 0.89650(15) 1.51883(11) 0.36968(12) 0.0173(2) Uani 1 1 d . . . . .
N14 N 0.92198(15) 1.03384(12) 0.76905(12) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.81412(15) 1.18372(13) 0.47948(13) 0.0133(2) Uani 1 1 d . . . . .
C4 C 0.88559(15) 1.38705(13) 0.43286(13) 0.0138(2) Uani 1 1 d . . . . .
C5 C 0.87471(15) 1.07036(12) 0.66152(13) 0.0136(2) Uani 1 1 d . . . . .
N15 N 0.57394(14) 0.37099(11) 0.75080(12) 0.0156(2) Uani 1 1 d . . . . .
N16 N 0.52305(14) 0.37422(11) 0.64207(12) 0.0156(2) Uani 1 1 d . . . . .
N17 N 0.39569(13) 0.18144(11) 0.64420(11) 0.0147(2) Uani 1 1 d . . . . .
N18 N 0.41457(14) 0.05938(11) 0.85084(12) 0.0158(2) Uani 1 1 d . . . . .
N19 N 0.47642(13) 0.18391(11) 0.80732(11) 0.0141(2) Uani 1 1 d . . . . .
N20 N 0.36776(16) 0.20230(12) 0.52091(12) 0.0187(2) Uani 1 1 d . . . . .
N21 N 0.30714(15) -0.03517(12) 0.73296(13) 0.0193(2) Uani 1 1 d . . . . .
N22 N 0.57619(15) 0.22565(12) 0.96766(12) 0.0183(2) Uani 1 1 d . . . . .
C6 C 0.46576(15) 0.25809(13) 0.68434(13) 0.0141(2) Uani 1 1 d . . . . .
C7 C 0.36896(15) 0.06328(13) 0.74653(14) 0.0147(2) Uani 1 1 d . . . . .
C8 C 0.54659(15) 0.25765(13) 0.84963(14) 0.0142(2) Uani 1 1 d . . . . .
H12A H 0.645(2) 1.425(2) 0.342(2) 0.026(5) Uiso 1 1 d . . . . .
H14A H 0.951(2) 1.095(2) 0.796(2) 0.023(4) Uiso 1 1 d . . . . .
H13A H 0.883(2) 1.549(2) 0.287(2) 0.024(5) Uiso 1 1 d . . . . .
H21A H 0.261(2) -0.098(2) 0.807(2) 0.029(5) Uiso 1 1 d . . . . .
H20A H 0.467(3) 0.206(2) 0.450(2) 0.032(5) Uiso 1 1 d . . . . .
H13B H 0.951(2) 1.5636(19) 0.3909(19) 0.021(4) Uiso 1 1 d . . . . .
H7 H 0.786(3) 0.908(2) 0.665(2) 0.036(5) Uiso 1 1 d . . . . .
H21B H 0.278(3) -0.018(2) 0.659(2) 0.031(5) Uiso 1 1 d . . . . .
H20B H 0.301(3) 0.282(2) 0.508(2) 0.033(5) Uiso 1 1 d . . . . .
H22A H 0.574(2) 0.134(2) 1.016(2) 0.031(5) Uiso 1 1 d . . . . .
H12B H 0.775(3) 1.375(2) 0.220(2) 0.032(5) Uiso 1 1 d . . . . .
H14B H 0.911(2) 0.949(2) 0.822(2) 0.029(5) Uiso 1 1 d . . . . .
H22B H 0.645(3) 0.277(2) 0.972(2) 0.038(6) Uiso 1 1 d . . . . .
H15 H 0.622(3) 0.448(3) 0.746(2) 0.046(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 1.2570(16) . ?
O2 N6 1.2578(15) . ?
O3 N6 1.2610(15) . ?
N1 N2 1.3302(15) . ?
N1 C1 1.3306(17) . ?
N2 C2 1.3574(16) . ?
N3 N4 1.3057(16) . ?
N3 C2 1.3901(17) . ?
N4 C1 1.3613(16) . ?
N5 N6 1.3121(16) . ?
N5 C1 1.3960(17) . ?
N7 N8 1.4083(15) . ?
N7 C5 1.3441(16) . ?
N7 H7 0.91(2) . ?
N8 C3 1.3013(16) . ?
N9 N12 1.4058(15) . ?
N9 C3 1.3609(16) . ?
N9 C4 1.3972(16) . ?
N10 N11 1.4061(14) . ?
N10 C4 1.3254(17) . ?
N11 C3 1.3530(17) . ?
N11 C5 1.3592(16) . ?
N12 H12A 0.90(2) . ?
N12 H12B 0.91(2) . ?
N13 C4 1.3355(17) . ?
N13 H13A 0.90(2) . ?
N13 H13B 0.88(2) . ?
N14 C5 1.3193(17) . ?
N14 H14A 0.89(2) . ?
N14 H14B 0.90(2) . ?
N15 N16 1.4096(15) . ?
N15 C8 1.3318(17) . ?
N15 H15 0.97(2) . ?
N16 C6 1.3024(17) . ?
N17 N20 1.3975(15) . ?
N17 C6 1.3630(17) . ?
N17 C7 1.3836(17) . ?
N18 N19 1.4000(14) . ?
N18 C7 1.3310(17) . ?
N19 C6 1.3564(17) . ?
N19 C8 1.3565(16) . ?
N20 H20A 0.92(2) . ?
N20 H20B 0.90(2) . ?
N21 C7 1.3312(17) . ?
N21 H21A 0.90(2) . ?
N21 H21B 0.90(2) . ?
N22 C8 1.3377(17) . ?
N22 H22A 0.94(2) . ?
N22 H22B 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 118.43(11) . . ?
N1 N2 C2 119.20(11) . . ?
N4 N3 C2 118.68(11) . . ?
N3 N4 C1 118.66(11) . . ?
N6 N5 C1 117.63(11) . . ?
O2 N6 O3 120.22(11) . . ?
O2 N6 N5 124.45(11) . . ?
O3 N6 N5 115.28(11) . . ?
N1 C1 N4 123.55(12) . . ?
N1 C1 N5 124.01(11) . . ?
N4 C1 N5 111.84(11) . . ?
O1 C2 N2 119.81(12) . . ?
O1 C2 N3 119.18(11) . . ?
N2 C2 N3 120.99(12) . . ?
N8 N7 H7 122.9(13) . . ?
C5 N7 N8 113.26(10) . . ?
C5 N7 H7 123.9(13) . . ?
C3 N8 N7 100.77(10) . . ?
C3 N9 N12 121.55(10) . . ?
C3 N9 C4 105.23(10) . . ?
C4 N9 N12 128.27(11) . . ?
C4 N10 N11 101.28(10) . . ?
C3 N11 N10 112.85(10) . . ?
C3 N11 C5 107.18(10) . . ?
C5 N11 N10 139.90(11) . . ?
N9 N12 H12A 107.8(12) . . ?
N9 N12 H12B 109.5(13) . . ?
H12A N12 H12B 110.7(18) . . ?
C4 N13 H13A 118.5(12) . . ?
C4 N13 H13B 118.4(12) . . ?
H13A N13 H13B 119.1(17) . . ?
C5 N14 H14A 120.8(12) . . ?
C5 N14 H14B 118.9(13) . . ?
H14A N14 H14B 119.7(17) . . ?
N8 C3 N9 138.97(12) . . ?
N8 C3 N11 114.58(11) . . ?
N11 C3 N9 106.45(11) . . ?
N10 C4 N9 114.06(11) . . ?
N10 C4 N13 125.98(12) . . ?
N13 C4 N9 119.95(12) . . ?
N7 C5 N11 104.18(11) . . ?
N14 C5 N7 127.46(12) . . ?
N14 C5 N11 128.35(12) . . ?
N16 N15 H15 118.7(14) . . ?
C8 N15 N16 112.88(11) . . ?
C8 N15 H15 128.4(14) . . ?
C6 N16 N15 101.03(10) . . ?
C6 N17 N20 130.17(11) . . ?
C6 N17 C7 106.17(11) . . ?
C7 N17 N20 123.35(11) . . ?
C7 N18 N19 101.12(10) . . ?
C6 N19 N18 113.39(10) . . ?
C6 N19 C8 106.74(11) . . ?
C8 N19 N18 139.86(11) . . ?
N17 N20 H20A 107.2(13) . . ?
N17 N20 H20B 111.6(13) . . ?
H20A N20 H20B 108.8(18) . . ?
C7 N21 H21A 120.6(13) . . ?
C7 N21 H21B 117.2(13) . . ?
H21A N21 H21B 118.0(18) . . ?
C8 N22 H22A 116.7(12) . . ?
C8 N22 H22B 115.9(14) . . ?
H22A N22 H22B 120.1(18) . . ?
N16 C6 N17 140.32(12) . . ?
N16 C6 N19 114.25(11) . . ?
N19 C6 N17 105.43(11) . . ?
N18 C7 N17 113.87(11) . . ?
N18 C7 N21 126.06(12) . . ?
N21 C7 N17 120.04(12) . . ?
N15 C8 N19 105.10(11) . . ?
N15 C8 N22 127.53(12) . . ?
N22 C8 N19 127.32(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N14 H14A O3 0.89(2) 1.89(2) 2.7721(15) 169.6(18) 2_777 yes
N13 H13A N5 0.90(2) 2.12(2) 3.0036(16) 166.4(17) 1_564 yes
N21 H21A O2 0.90(2) 2.11(2) 2.9287(15) 152.0(17) 1_445 yes
N13 H13B N10 0.88(2) 2.20(2) 3.0782(16) 174.7(17) 2_786 yes
N7 H7 N2 0.91(2) 1.87(2) 2.7649(16) 164(2) . yes
N21 H21B N8 0.90(2) 2.14(2) 2.9839(16) 156.7(18) 2_666 yes
N20 H20B O1 0.90(2) 2.32(2) 2.9219(15) 124.0(17) 2_666 yes
N22 H22A N18 0.94(2) 2.10(2) 3.0216(16) 168.4(18) 2_657 yes
N14 H14B O2 0.90(2) 2.29(2) 2.9732(15) 133.0(16) . yes
N14 H14B N1 0.90(2) 2.16(2) 2.9805(16) 150.9(17) . yes
N15 H15 O1 0.97(2) 1.60(3) 2.5548(15) 168(2) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 O1 -176.11(12) . . . . ?
N1 N2 C2 N3 5.54(19) . . . . ?
N2 N1 C1 N4 -5.82(19) . . . . ?
N2 N1 C1 N5 -176.15(11) . . . . ?
N3 N4 C1 N1 4.97(19) . . . . ?
N3 N4 C1 N5 176.35(11) . . . . ?
N4 N3 C2 O1 175.28(12) . . . . ?
N4 N3 C2 N2 -6.36(18) . . . . ?
N6 N5 C1 N1 -32.71(18) . . . . ?
N6 N5 C1 N4 155.95(11) . . . . ?
C1 N1 N2 C2 0.43(18) . . . . ?
C1 N5 N6 O2 -7.75(18) . . . . ?
C1 N5 N6 O3 174.87(11) . . . . ?
C2 N3 N4 C1 1.18(17) . . . . ?
N7 N8 C3 N9 -179.22(16) . . . . ?
N7 N8 C3 N11 1.08(14) . . . . ?
N8 N7 C5 N11 -1.19(14) . . . . ?
N8 N7 C5 N14 178.24(12) . . . . ?
N10 N11 C3 N8 -179.35(11) . . . . ?
N10 N11 C3 N9 0.86(14) . . . . ?
N10 N11 C5 N7 178.11(14) . . . . ?
N10 N11 C5 N14 -1.3(3) . . . . ?
N11 N10 C4 N9 -3.11(14) . . . . ?
N11 N10 C4 N13 176.18(13) . . . . ?
N12 N9 C3 N8 20.7(2) . . . . ?
N12 N9 C3 N11 -159.59(11) . . . . ?
N12 N9 C4 N10 158.67(12) . . . . ?
N12 N9 C4 N13 -20.7(2) . . . . ?
C3 N9 C4 N10 3.78(15) . . . . ?
C3 N9 C4 N13 -175.55(12) . . . . ?
C3 N11 C5 N7 1.75(13) . . . . ?
C3 N11 C5 N14 -177.67(13) . . . . ?
C4 N9 C3 N8 177.68(16) . . . . ?
C4 N9 C3 N11 -2.60(13) . . . . ?
C4 N10 N11 C3 1.35(14) . . . . ?
C4 N10 N11 C5 -174.88(15) . . . . ?
C5 N7 N8 C3 0.12(14) . . . . ?
C5 N11 C3 N8 -1.89(15) . . . . ?
C5 N11 C3 N9 178.32(10) . . . . ?
N15 N16 C6 N17 -179.62(16) . . . . ?
N15 N16 C6 N19 -0.12(14) . . . . ?
N16 N15 C8 N19 -0.09(14) . . . . ?
N16 N15 C8 N22 -177.84(12) . . . . ?
N18 N19 C6 N16 -179.87(11) . . . . ?
N18 N19 C6 N17 -0.20(14) . . . . ?
N18 N19 C8 N15 179.94(14) . . . . ?
N18 N19 C8 N22 -2.3(3) . . . . ?
N19 N18 C7 N17 -1.04(14) . . . . ?
N19 N18 C7 N21 177.01(13) . . . . ?
N20 N17 C6 N16 5.4(3) . . . . ?
N20 N17 C6 N19 -174.14(12) . . . . ?
N20 N17 C7 N18 175.23(11) . . . . ?
N20 N17 C7 N21 -2.95(19) . . . . ?
C6 N17 C7 N18 0.98(15) . . . . ?
C6 N17 C7 N21 -177.20(12) . . . . ?
C6 N19 C8 N15 0.02(14) . . . . ?
C6 N19 C8 N22 177.77(13) . . . . ?
C7 N17 C6 N16 179.10(16) . . . . ?
C7 N17 C6 N19 -0.43(13) . . . . ?
C7 N18 N19 C6 0.75(14) . . . . ?
C7 N18 N19 C8 -179.17(15) . . . . ?
C8 N15 N16 C6 0.13(14) . . . . ?
C8 N19 C6 N16 0.07(15) . . . . ?
C8 N19 C6 N17 179.74(10) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JS1507
_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 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.641
