# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_js424c
_database_code_depnum_ccdc_archive 'CCDC 2378050'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-08-16 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_audit_creation_date             2024-04-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H3 N8 O2, C3 H7 N8'
_chemical_formula_sum            'C5 H10 N16 O2'
_chemical_formula_weight         326.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C5N10O10H10
_chemical_oxdiff_usercomment     JS1038
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                   7.5670(4)
_cell_length_b                   8.0991(5)
_cell_length_c                   10.3845(5)
_cell_angle_alpha                75.305(5)
_cell_angle_beta                 87.190(4)
_cell_angle_gamma                78.201(5)
_cell_volume                     602.60(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4913
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.7780
_cell_measurement_theta_min      5.7960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69731
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.96a (Rigaku Oxford Diffraction, 2023)
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            'reddish yellow'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.798
_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
1 0 0 0.1963
-1 0 0 0.1388
0 0 -1 0.0256
0 0 1 0.0243
0 1 1 0.0057
0 -1 -1 0.0057

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.011
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
1.0004 0.0009 0.0026 0.0637 -0.1966 0.0242
-1.0004 -0.0009 -0.0026 -0.0637 0.1966 -0.0242
0.0007 0.0010 -0.9996 0.0689 0.0391 0.1313
-0.0007 -0.0010 0.9996 -0.0689 -0.0391 -0.1313
-0.0003 0.9977 1.0023 -0.2180 -0.0290 0.0020
0.0003 -0.9977 -1.0023 0.2180 0.0290 -0.0020

_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8176
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.562
_diffrn_reflns_theta_min         4.402
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  -8.00   0.50    0.28    --  -47.82  41.00 -74.00   82
  2  ω   -116.00 -39.00   0.50    0.28    --  -47.82 -41.00 132.00  154
  3  ω    -23.00  37.00   0.50    0.28    --   47.82 -41.00 132.00  120
  4  ω     49.00 120.00   0.50    0.28    --   47.82  41.00 -74.00  142
  5  ω    -49.00 -24.00   0.50    1.11    --  -91.75  41.00 -74.00   50
  6  ω   -144.00-119.00   0.50    1.11    --  -91.75 -41.00 132.00   50
  7  ω    125.00 177.00   0.50    1.11    --  113.25  41.00 -74.00  104
  8  ω     -5.00  21.00   0.50    0.28    --  -47.82  41.00 -74.00   52
  9  ω     43.00  90.00   0.50    0.28    --   47.82-125.00 150.00   94
 10  ω     27.00  71.00   0.50    0.28    --   47.82 -77.00-180.00   88
 11  ω    -15.00  10.00   0.50    0.28    --   47.82 -19.00-150.00   50
 12  ω     43.00  68.00   0.50    0.28    --   47.82-125.00-180.00   50
 13  ω    -77.00 -26.00   0.50    1.11    --  -91.75 125.00 -30.00  102
 14  ω    -51.00 -21.00   0.50    1.11    --  -91.75  45.00  90.00   60
 15  ω    -53.00 -28.00   0.50    1.11    --  -91.75  45.00  60.00   50
 16  ω     43.00  69.00   0.50    1.11    --  113.25 -94.00-120.00   52
 17  ω    130.00 156.00   0.50    1.11    --  113.25  61.00 150.00   52
 18  ω     44.00  76.00   0.50    1.11    --  113.25-125.00  30.00   64
 19  ω     43.00  69.00   0.50    1.11    --  113.25 -94.00 150.00   52
 20  ω    147.00 173.00   0.50    1.11    --  113.25  45.00-150.00   52
 21  ω     45.00  72.00   0.50    1.11    --  113.25 -77.00 -90.00   54
 22  ω     82.00 108.00   0.50    1.11    --  113.25-125.00-120.00   52
 23  ω     78.00 104.00   0.50    1.11    --  113.25 -94.00  60.00   52
 24  ω     68.00 101.00   0.50    1.11    --  113.25 -94.00 -60.00   66
 25  ω     43.00  68.00   0.50    1.11    --  113.25 -61.00 -60.00   50
 26  ω     42.00  67.00   0.50    1.11    --  113.25 -61.00 -90.00   50
 27  ω    117.00 143.00   0.50    1.11    --  113.25 125.00-120.00   52
 28  ω     46.00  72.00   0.50    1.11    --  113.25 -94.00 -90.00   52
 29  ω     74.00 103.00   0.50    1.11    --  113.25 -94.00 -90.00   58
 30  ω     65.00  91.00   0.50    1.11    --  113.25 -77.00  30.00   52
 31  ω    103.00 128.00   0.50    1.11    --  113.25  15.00  30.00   50
 32  ω    142.00 175.00   0.50    1.11    --  113.25  15.00  30.00   66
 33  ω    107.00 144.00   0.50    1.11    --  113.25  45.00-150.00   74
 34  ω    110.00 174.00   0.50    1.11    --  113.25  77.00 -60.00  128
 35  ω     78.00 104.00   0.50    1.11    --  113.25 -94.00 -30.00   52
 36  ω     50.00  98.00   0.50    1.11    --  113.25 -94.00-180.00   96
 37  ω    151.00 178.00   0.50    1.11    --  113.25 125.00 150.00   54
 38  ω    136.00 174.00   0.50    1.11    --  113.25  61.00-120.00   76
 39  ω    112.00 178.00   0.50    1.11    --  113.25  77.00-150.00  132
 40  ω    104.00 172.00   0.50    1.11    --  113.25  15.00-180.00  136
 41  ω     50.00 104.00   0.50    1.11    --  113.25 -94.00 120.00  108
 42  ω    128.00 178.00   0.50    1.11    --  113.25 125.00-180.00  100
 43  ω     42.00  67.00   0.50    1.11    --  113.25 -61.00-120.00   50
 44  ω     43.00  68.00   0.50    1.11    --  113.25 -61.00 -30.00   50
 45  ω     76.00 101.00   0.50    1.11    --  113.25 -94.00-150.00   50
 46  ω     65.00  91.00   0.50    1.11    --  113.25 -94.00  30.00   52
 47  ω     65.00 104.00   0.50    1.11    --  113.25 -94.00  90.00   78
 48  ω    111.00 169.00   0.50    1.11    --  113.25  61.00  90.00  116
 49  ω    101.00 135.00   0.50    1.11    --  113.25  30.00 -90.00   68
 50  ω     43.00  69.00   0.50    1.11    --  113.25 -61.00-180.00   52
 51  ω     47.00  74.00   0.50    1.11    --  113.25 -77.00-180.00   54
 52  ω     45.00  70.00   0.50    1.11    --  113.25 -77.00 -60.00   50
 53  ω     54.00  80.00   0.50    1.11    --  113.25 -77.00   0.00   52
 54  ω     72.00 104.00   0.50    1.11    --  113.25 -94.00-120.00   64
 55  ω     73.00  98.00   0.50    1.11    --  113.25 -77.00 120.00   50
 56  ω     68.00  93.00   0.50    1.11    --  113.25-125.00-180.00   50
 57  ω     48.00  74.00   0.50    1.11    --  113.25-125.00  60.00   52
 58  ω     78.00 103.00   0.50    1.11    --  113.25-125.00  60.00   50
 59  ω     66.00  91.00   0.50    1.11    --  113.25-125.00 120.00   50
 60  ω    111.00 137.00   0.50    1.11    --  113.25  61.00  30.00   52
 61  ω    111.00 136.00   0.50    1.11    --  113.25  45.00 -60.00   50
 62  ω     42.00  67.00   0.50    1.11    --  113.25 -61.00  30.00   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      0.0639379000
_diffrn_orient_matrix_UB_12      -0.1491224000
_diffrn_orient_matrix_UB_13      -0.0690502000
_diffrn_orient_matrix_UB_21      -0.1964020000
_diffrn_orient_matrix_UB_22      0.0103266000
_diffrn_orient_matrix_UB_23      -0.0392733000
_diffrn_orient_matrix_UB_31      0.0244101000
_diffrn_orient_matrix_UB_32      0.1338523000
_diffrn_orient_matrix_UB_33      -0.1311945000
_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                2227
_reflns_number_total             2563
_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 1.171.43.96a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_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         0.314
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.052
_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)+(0.0897P)²+0.1255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1326
_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 0.29319(17) -0.15776(17) 0.69673(14) 0.0322(3) Uani 1 1 d . . . . .
O2 O 0.03363(16) 0.02152(16) 0.65720(12) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.55442(18) 0.16222(16) 0.68638(13) 0.0199(3) Uani 1 1 d . . . . .
N2 N 0.6432(2) -0.01045(17) 0.69767(14) 0.0235(3) Uani 1 1 d . . . . .
N3 N 0.41471(18) 0.39598(17) 0.76377(12) 0.0202(3) Uani 1 1 d . . . . .
N4 N 0.36545(17) 0.40905(17) 0.63247(13) 0.0194(3) Uani 1 1 d . . . . .
N5 N 0.26348(19) 0.43031(17) 0.44039(14) 0.0219(3) Uani 1 1 d . . . . .
N6 N 0.38590(18) 0.27027(17) 0.47023(13) 0.0223(3) Uani 1 1 d . . . . .
N7 N 0.60881(19) 0.16519(17) 0.90846(14) 0.0221(3) Uani 1 1 d . . . . .
N8 N 0.14317(19) 0.66636(18) 0.54100(15) 0.0232(3) Uani 1 1 d . . . . .
N9 N -0.37616(19) 0.64370(18) 0.91048(14) 0.0241(3) Uani 1 1 d . . . . .
N10 N -0.25970(19) 0.49894(17) 0.98977(14) 0.0231(3) Uani 1 1 d . . . . .
N11 N -0.11039(18) 0.41769(17) 0.80760(13) 0.0210(3) Uani 1 1 d . . . . .
N12 N 0.00378(18) 0.29601(17) 0.76247(13) 0.0216(3) Uani 1 1 d . . . . .
N13 N 0.09707(18) 0.15506(17) 0.98496(13) 0.0220(3) Uani 1 1 d . . . . .
N14 N -0.01495(18) 0.27146(17) 1.03005(13) 0.0221(3) Uani 1 1 d . . . . .
N15 N 0.21858(18) 0.02500(18) 0.82196(14) 0.0233(3) Uani 1 1 d . . . . .
N16 N 0.17727(18) -0.03360(18) 0.72330(13) 0.0227(3) Uani 1 1 d . . . . .
C1 C 0.5256(2) 0.2399(2) 0.79252(15) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.2485(2) 0.5153(2) 0.53707(15) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.4417(2) 0.2680(2) 0.58665(15) 0.0196(3) Uani 1 1 d . . . . .
C4 C -0.1297(2) 0.3943(2) 0.93948(15) 0.0205(3) Uani 1 1 d . . . . .
C5 C 0.0950(2) 0.1610(2) 0.85211(16) 0.0208(3) Uani 1 1 d . . . . .
H10 H -0.275(3) 0.483(3) 1.081(2) 0.030(5) Uiso 1 1 d . . . . .
H8A H 0.174(3) 0.727(3) 0.589(2) 0.028(5) Uiso 1 1 d . . . . .
H2A H 0.570(3) -0.061(3) 0.666(2) 0.033(6) Uiso 1 1 d . . . . .
H7A H 0.567(3) 0.206(3) 0.977(2) 0.023(5) Uiso 1 1 d . . . . .
H9A H -0.313(3) 0.720(3) 0.866(2) 0.023(5) Uiso 1 1 d . . . . .
H9B H -0.436(4) 0.605(3) 0.853(2) 0.036(6) Uiso 1 1 d . . . . .
H5 H 0.212(4) 0.462(4) 0.360(3) 0.045(7) Uiso 1 1 d . . . . .
H8B H 0.085(3) 0.717(3) 0.469(3) 0.031(6) Uiso 1 1 d . . . . .
H7B H 0.676(3) 0.061(3) 0.918(2) 0.031(6) Uiso 1 1 d . . . . .
H2B H 0.748(4) -0.008(3) 0.646(3) 0.041(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 N16 1.2701(18) . ?
O2 N16 1.2534(18) . ?
N1 N2 1.4003(17) . ?
N1 C1 1.389(2) . ?
N1 C3 1.3682(19) . ?
N2 H2A 0.87(3) . ?
N2 H2B 0.94(3) . ?
N3 N4 1.4035(18) . ?
N3 C1 1.3385(19) . ?
N4 C2 1.3589(19) . ?
N4 C3 1.358(2) . ?
N5 N6 1.4027(18) . ?
N5 C2 1.342(2) . ?
N5 H5 0.89(3) . ?
N6 C3 1.294(2) . ?
N7 C1 1.327(2) . ?
N7 H7A 0.88(2) . ?
N7 H7B 0.88(3) . ?
N8 C2 1.326(2) . ?
N8 H8A 0.86(3) . ?
N8 H8B 0.85(3) . ?
N9 N10 1.4099(18) . ?
N9 H9A 0.88(2) . ?
N9 H9B 0.92(3) . ?
N10 C4 1.339(2) . ?
N10 H10 0.93(2) . ?
N11 N12 1.3355(18) . ?
N11 C4 1.339(2) . ?
N12 C5 1.333(2) . ?
N13 N14 1.2980(19) . ?
N13 C5 1.369(2) . ?
N14 C4 1.371(2) . ?
N15 N16 1.3081(19) . ?
N15 C5 1.383(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
C1 N1 N2 123.90(13) . . ?
C3 N1 N2 127.90(13) . . ?
C3 N1 C1 106.05(12) . . ?
N1 N2 H2A 106.8(16) . . ?
N1 N2 H2B 107.4(16) . . ?
H2A N2 H2B 111(2) . . ?
C1 N3 N4 100.90(12) . . ?
C2 N4 N3 139.03(13) . . ?
C3 N4 N3 113.67(12) . . ?
C3 N4 C2 106.95(13) . . ?
N6 N5 H5 115.9(18) . . ?
C2 N5 N6 113.73(13) . . ?
C2 N5 H5 130.3(18) . . ?
C3 N6 N5 100.68(12) . . ?
C1 N7 H7A 117.3(14) . . ?
C1 N7 H7B 117.8(15) . . ?
H7A N7 H7B 122(2) . . ?
C2 N8 H8A 119.5(16) . . ?
C2 N8 H8B 113.6(16) . . ?
H8A N8 H8B 119(2) . . ?
N10 N9 H9A 109.9(14) . . ?
N10 N9 H9B 108.1(16) . . ?
H9A N9 H9B 110(2) . . ?
N9 N10 H10 115.4(14) . . ?
C4 N10 N9 123.35(13) . . ?
C4 N10 H10 121.2(14) . . ?
N12 N11 C4 118.15(13) . . ?
C5 N12 N11 117.65(13) . . ?
N14 N13 C5 119.15(13) . . ?
N13 N14 C4 116.93(13) . . ?
N16 N15 C5 116.71(13) . . ?
O1 N16 N15 115.67(13) . . ?
O2 N16 O1 119.35(13) . . ?
O2 N16 N15 124.97(14) . . ?
N3 C1 N1 113.74(13) . . ?
N7 C1 N1 121.45(14) . . ?
N7 C1 N3 124.75(14) . . ?
N5 C2 N4 103.91(13) . . ?
N8 C2 N4 127.41(14) . . ?
N8 C2 N5 128.68(14) . . ?
N4 C3 N1 105.30(13) . . ?
N6 C3 N1 139.92(14) . . ?
N6 C3 N4 114.73(13) . . ?
N10 C4 N11 120.53(14) . . ?
N10 C4 N14 116.13(14) . . ?
N11 C4 N14 123.25(14) . . ?
N12 C5 N13 122.90(14) . . ?
N12 C5 N15 124.84(14) . . ?
N13 C5 N15 111.56(13) . . ?

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 O1 0.86(3) 1.97(3) 2.818(2) 169(2) 1_565 yes
N5 H5 N11 0.89(3) 1.88(3) 2.7551(19) 166(3) 2_566 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
N2 N1 C1 N3 -170.29(14) . . . . ?
N2 N1 C1 N7 12.3(2) . . . . ?
N2 N1 C3 N4 169.21(14) . . . . ?
N2 N1 C3 N6 -8.2(3) . . . . ?
N3 N4 C2 N5 -172.41(17) . . . . ?
N3 N4 C2 N8 6.7(3) . . . . ?
N3 N4 C3 N1 -3.97(17) . . . . ?
N3 N4 C3 N6 174.17(13) . . . . ?
N4 N3 C1 N1 3.25(16) . . . . ?
N4 N3 C1 N7 -179.46(15) . . . . ?
N5 N6 C3 N1 177.78(19) . . . . ?
N5 N6 C3 N4 0.56(18) . . . . ?
N6 N5 C2 N4 0.55(17) . . . . ?
N6 N5 C2 N8 -178.57(15) . . . . ?
N9 N10 C4 N11 -3.7(2) . . . . ?
N9 N10 C4 N14 172.81(14) . . . . ?
N11 N12 C5 N13 -10.0(2) . . . . ?
N11 N12 C5 N15 -179.63(14) . . . . ?
N12 N11 C4 N10 -170.73(14) . . . . ?
N12 N11 C4 N14 13.0(2) . . . . ?
N13 N14 C4 N10 171.52(13) . . . . ?
N13 N14 C4 N11 -12.1(2) . . . . ?
N14 N13 C5 N12 11.0(2) . . . . ?
N14 N13 C5 N15 -178.18(13) . . . . ?
N16 N15 C5 N12 -40.5(2) . . . . ?
N16 N15 C5 N13 148.87(14) . . . . ?
C1 N1 C3 N4 5.57(16) . . . . ?
C1 N1 C3 N6 -171.8(2) . . . . ?
C1 N3 N4 C2 172.41(18) . . . . ?
C1 N3 N4 C3 0.52(16) . . . . ?
C2 N4 C3 N1 -178.42(12) . . . . ?
C2 N4 C3 N6 -0.27(19) . . . . ?
C2 N5 N6 C3 -0.69(17) . . . . ?
C3 N1 C1 N3 -5.81(18) . . . . ?
C3 N1 C1 N7 176.79(14) . . . . ?
C3 N4 C2 N5 -0.18(16) . . . . ?
C3 N4 C2 N8 178.96(16) . . . . ?
C4 N11 N12 C5 -1.8(2) . . . . ?
C5 N13 N14 C4 0.1(2) . . . . ?
C5 N15 N16 O1 179.55(14) . . . . ?
C5 N15 N16 O2 -1.7(2) . . . . ?

_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 JS1038
_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 1.525
_oxdiff_exptl_absorpt_empirical_full_min 0.627
####################################################################### 
# 
# 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_js724a
_database_code_depnum_ccdc_archive 'CCDC 2378052'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-08-16 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_audit_creation_date             2024-07-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H3 N7 O2'
_chemical_formula_sum            'C2 H3 N7 O2'
_chemical_formula_weight         157.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C2  H3  N7  O2  '
_chemical_oxdiff_usercomment     JS1109
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.3390(3)
_cell_length_b                   7.8421(3)
_cell_length_c                   15.2539(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1117.15(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4046
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.4190
_cell_measurement_theta_min      5.7900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.433
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.130a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 2 0.0099
0 0 -2 0.0075
1 -1 0 0.0410
-1 1 0 0.0771
1 1 0 0.0741
-1 -1 0 0.0379

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.017
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
0.0015 0.0034 2.0042 0.1795 -0.0798 -0.0491
-0.0015 -0.0034 -2.0042 -0.1795 0.0798 0.0491
0.9915 -1.0154 -0.0222 -0.1082 -0.2342 -0.0039
-0.9915 1.0154 0.0222 0.1082 0.2342 0.0039
0.9975 1.0056 -0.0059 -0.0339 0.0729 -0.2440
-0.9975 -1.0056 0.0059 0.0339 -0.0729 0.2440

_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6601
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.965
_diffrn_reflns_theta_min         5.801
_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 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  79.00   0.50    0.97    --  113.25-125.00-120.00   62
  2  ω     52.00 108.00   0.50    0.97    --  113.25-125.00   0.00  112
  3  ω   -116.00 -29.00   0.50    0.24    --  -47.47 -71.00  11.00  174
  4  ω   -138.00-102.00   0.50    0.97    --  -91.75 -54.00 156.00   72
  5  ω   -147.00-122.00   0.50    0.97    --  -91.75-107.00 -73.00   50
  6  ω    -63.00 -22.00   0.50    0.97    --  -91.75  54.00 -58.00   82
  7  ω     -8.00  19.00   0.50    0.24    --  -47.47  19.00 -60.00   54
  8  ω    -27.00  26.00   0.50    0.24    --   47.47 -19.00   0.00  106
  9  ω     54.00  96.00   0.50    0.97    --  113.25 -77.00 -60.00   84
 10  ω     60.00  98.00   0.50    0.97    --  113.25 -77.00 -30.00   76
 11  ω     49.00  81.00   0.50    0.97    --  113.25 -71.00  11.00   64
 12  ω     42.00  67.00   0.50    0.97    --  113.25 -61.00  30.00   50
 13  ω    107.00 144.00   0.50    0.97    --  113.25 107.00  25.00   74
 14  ω     42.00  67.00   0.50    0.97    --  113.25 -61.00 -90.00   50
 15  ω     43.00  69.00   0.50    0.97    --  113.25 -61.00  60.00   52
 16  ω     68.00  93.00   0.50    0.97    --  113.25 -77.00  90.00   50
 17  ω    130.00 157.00   0.50    0.97    --  113.25  15.00 120.00   54
 18  ω    113.00 177.00   0.50    0.97    --  113.25  61.00 120.00  128
 19  ω    125.00 177.00   0.50    0.97    --  113.25  71.00 142.00  104
 20  ω    113.00 149.00   0.50    0.97    --  113.25  61.00  90.00   72
 21  ω    109.00 178.00   0.50    0.97    --  113.25  61.00  60.00  138
 22  ω    105.00 138.00   0.50    0.97    --  113.25  45.00 120.00   66
 23  ω    120.00 147.00   0.50    0.97    --  113.25  77.00   0.00   54
 24  ω    124.00 150.00   0.50    0.97    --  113.25  45.00 -30.00   52
 25  ω    101.00 135.00   0.50    0.97    --  113.25  45.00 -90.00   68
 26  ω    128.00 153.00   0.50    0.97    --  113.25  30.00 -90.00   50
 27  ω    151.00 178.00   0.50    0.97    --  113.25  45.00 -90.00   54
 28  ω    146.00 173.00   0.50    0.97    --  113.25  61.00-180.00   54
;
_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      -0.0700131000
_diffrn_orient_matrix_UB_12      0.0362637000
_diffrn_orient_matrix_UB_13      0.0895452000
_diffrn_orient_matrix_UB_21      -0.0808891000
_diffrn_orient_matrix_UB_22      0.1525513000
_diffrn_orient_matrix_UB_23      -0.0400303000
_diffrn_orient_matrix_UB_31      -0.1255404000
_diffrn_orient_matrix_UB_32      -0.1182577000
_diffrn_orient_matrix_UB_33      -0.0242277000
_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                1013
_reflns_number_total             1187
_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 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.130a (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         0.396
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.041
_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)+(0.1045P)²+0.4815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1494
_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 0.22932(14) 0.43645(17) 0.48873(9) 0.0259(4) Uani 1 1 d . . . . .
O2 O 0.04141(15) 0.27535(18) 0.46924(10) 0.0279(4) Uani 1 1 d . . . . .
N5 N 0.21952(16) 0.2554(2) 0.37463(10) 0.0216(4) Uani 1 1 d . . . . .
N4 N 0.57484(15) 0.1310(2) 0.33312(11) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.42572(15) 0.42546(19) 0.35427(10) 0.0206(4) Uani 1 1 d . . . . .
N3 N 0.43532(15) 0.1239(2) 0.34526(10) 0.0212(4) Uani 1 1 d . . . . .
N7 N 0.78150(17) 0.2892(2) 0.34375(11) 0.0231(4) Uani 1 1 d . . . . .
N2 N 0.56587(15) 0.43526(19) 0.34579(10) 0.0211(4) Uani 1 1 d . . . . .
N6 N 0.16119(16) 0.32683(19) 0.44997(10) 0.0222(4) Uani 1 1 d . . . . .
C6 C 0.6396(2) 0.2856(2) 0.34269(12) 0.0208(4) Uani 1 1 d . . . . .
C5 C 0.3674(2) 0.2703(2) 0.36116(12) 0.0207(4) Uani 1 1 d . . . . .
H7A H 0.832(3) 0.194(3) 0.3446(17) 0.027(6) Uiso 1 1 d . . . . .
H5 H 0.178(3) 0.154(4) 0.3656(17) 0.031(6) Uiso 1 1 d . . . . .
H7B H 0.827(3) 0.389(4) 0.3486(18) 0.033(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 N6 1.222(2) . ?
O2 N6 1.225(2) . ?
N5 N6 1.390(2) . ?
N5 C5 1.401(2) . ?
N5 H5 0.89(3) . ?
N4 N3 1.317(2) . ?
N4 C6 1.363(2) . ?
N1 N2 1.317(2) . ?
N1 C5 1.337(2) . ?
N3 C5 1.334(2) . ?
N7 C6 1.326(2) . ?
N7 H7A 0.88(3) . ?
N7 H7B 0.89(3) . ?
N2 C6 1.362(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
N6 N5 C5 118.30(15) . . ?
N6 N5 H5 108.5(17) . . ?
C5 N5 H5 118.5(16) . . ?
N3 N4 C6 117.49(15) . . ?
N2 N1 C5 117.74(14) . . ?
N4 N3 C5 117.38(15) . . ?
C6 N7 H7A 121.3(16) . . ?
C6 N7 H7B 119.8(17) . . ?
H7A N7 H7B 119(2) . . ?
N1 N2 C6 117.09(14) . . ?
O1 N6 O2 126.24(16) . . ?
O1 N6 N5 118.66(14) . . ?
O2 N6 N5 115.06(15) . . ?
N7 C6 N4 117.67(16) . . ?
N7 C6 N2 119.11(16) . . ?
N2 C6 N4 123.10(18) . . ?
N1 C5 N5 119.27(16) . . ?
N3 C5 N5 115.08(15) . . ?
N3 C5 N1 125.10(17) . . ?

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
N5 H5 N1 0.89(3) 2.05(3) 2.938(2) 175(2) 8_655 yes
N7 H7B N4 0.89(3) 2.12(3) 3.002(2) 168(2) 8_765 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
N4 N3 C5 N5 -179.26(15) . . . . ?
N4 N3 C5 N1 9.4(3) . . . . ?
N1 N2 C6 N4 11.4(3) . . . . ?
N1 N2 C6 N7 -172.78(16) . . . . ?
N3 N4 C6 N7 170.00(17) . . . . ?
N3 N4 C6 N2 -14.1(3) . . . . ?
N2 N1 C5 N5 176.86(16) . . . . ?
N2 N1 C5 N3 -12.2(3) . . . . ?
N6 N5 C5 N1 -60.9(2) . . . . ?
N6 N5 C5 N3 127.26(17) . . . . ?
C6 N4 N3 C5 3.6(2) . . . . ?
C5 N5 N6 O1 19.5(2) . . . . ?
C5 N5 N6 O2 -162.79(16) . . . . ?
C5 N1 N2 C6 1.5(2) . . . . ?

_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 JS1109
_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 1.681
_oxdiff_exptl_absorpt_empirical_full_min 0.704
####################################################################### 
# 
# 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_js124h
_database_code_depnum_ccdc_archive 'CCDC 2378051'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-08-16 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_audit_creation_date             2024-01-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H2 N7 O2, C3 H7 N8, H2 O'
_chemical_formula_sum            'C5 H11 N15 O3'
_chemical_formula_weight         329.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4N6H4O8
_chemical_oxdiff_usercomment     JS864
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                   7.8417(3)
_cell_length_b                   8.7831(3)
_cell_length_c                   9.5513(4)
_cell_angle_alpha                102.593(3)
_cell_angle_beta                 102.923(3)
_cell_angle_gamma                100.960(3)
_cell_volume                     605.70(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4638
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.5530
_cell_measurement_theta_min      4.9270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.309
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.96a (Rigaku Oxford Diffraction, 2023)
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    1.805
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -1 3 0.0885
-4 2 -2 0.0814
1 -5 -1 0.0200
-1 5 1 0.0518
2 2 3 0.0585
3 3 -5 0.0437
-2 -4 5 0.0400
-2 6 -1 0.0400
-2 -5 1 0.0290
3 3 -1 0.0658
0 -6 1 0.0179

_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.073
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
3.8147 -0.6594 2.7624 -0.4205 -0.8819 0.2132
-4.0854 2.1997 -2.4595 0.3755 0.7882 -0.4875
0.5629 -5.1003 -1.2638 0.1887 0.3933 0.8998
-1.1392 5.3211 0.8870 -0.1313 -0.2727 -0.9531
2.3382 2.4563 2.6488 -0.4011 -0.8398 -0.3658
2.5350 2.6797 -5.4102 -0.8865 0.4232 -0.1873
-1.5981 -4.0320 4.8585 0.7976 -0.3811 0.4676
-1.5535 5.6608 -1.1979 -0.2010 0.0971 -0.9748
-1.7599 -4.8102 1.1346 0.6743 0.2784 0.6839
3.3918 3.4005 -1.4613 -0.8592 -0.3554 -0.3680
0.0802 -5.5398 0.6600 0.4013 0.1651 0.9009

_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7580
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.706
_diffrn_reflns_theta_min         4.937
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  15.00   0.50    0.07    --  -46.86  19.00-180.00   90
  2  ω    -38.00 -11.00   0.50    0.28    --  -86.25  30.00-150.00   54
  3  ω    -30.00  27.00   0.50    0.07    --  -46.86  19.00 -60.00  114
  4  ω    -31.00  28.00   0.50    0.07    --  -46.86  19.00  60.00  118
  5  ω     87.00 112.00   0.50    0.07    --   46.86-162.00  94.00   50
  6  ω     75.00 104.00   0.50    0.28    --  107.75 -94.00 120.00   58
  7  ω     70.00  95.00   0.50    0.28    --  107.75-162.00  94.00   50
  8  ω     60.00 101.00   0.50    0.28    --  107.75 -94.00  60.00   82
  9  ω     70.00 104.00   0.50    0.28    --  107.75 -94.00 -30.00   68
 10  ω     45.00  98.00   0.50    0.28    --  107.75 -94.00  30.00  106
 11  ω     62.00 101.00   0.50    0.28    --  107.75 -94.00 -60.00   78
 12  ω     41.00 104.00   0.50    0.28    --  107.75 -94.00 -90.00  126
 13  ω     51.00  78.00   0.50    0.28    --  107.75-117.00-115.00   54
 14  ω     74.00 103.00   0.50    0.28    --  107.75 -94.00-150.00   58
 15  ω     42.00 103.00   0.50    0.28    --  107.75 -94.00-180.00  122
 16  ω     61.00  88.00   0.50    0.07    --   46.86-117.00-115.00   54
 17  ω     78.00 103.00   0.50    0.28    --  107.75 -94.00  90.00   50
 18  ω     47.00  73.00   0.50    0.28    --  107.75 -77.00 -90.00   52
 19  ω     72.00  98.00   0.50    0.28    --  107.75 -77.00-150.00   52
 20  ω     41.00  91.00   0.50    0.28    --  107.75 -77.00   0.00  100
 21  ω     35.00  68.00   0.50    0.28    --  107.75 -61.00  60.00   66
 22  ω     40.00  67.00   0.50    0.28    --  107.75 -77.00 120.00   54
 23  ω     72.00  99.00   0.50    0.28    --  107.75 -77.00 120.00   54
 24  ω     39.00  69.00   0.50    0.28    --  107.75 -61.00 120.00   60
 25  ω     39.00  64.00   0.50    0.28    --  107.75 -61.00  90.00   50
 26  ω     36.00  61.00   0.50    0.28    --  107.75 -61.00 -30.00   50
 27  ω     36.00  68.00   0.50    0.28    --  107.75 -61.00-150.00   64
 28  ω    -25.00  27.00   0.50    0.07    --   46.86 -19.00-120.00  104
 29  ω     84.00 117.00   0.50    0.07    --   46.86 162.00 122.00   66
 30  ω     89.00 114.00   0.50    0.28    --  107.75 162.00 122.00   50
 31  ω     97.00 155.00   0.50    0.28    --  107.75 125.00  90.00  116
 32  ω    103.00 150.00   0.50    0.28    --  107.75 117.00 -27.00   94
 33  ω     96.00 137.00   0.50    0.28    --  107.75  30.00-150.00   82
 34  ω    113.00 156.00   0.50    0.28    --  107.75  77.00-180.00   86
 35  ω    124.00 152.00   0.50    0.28    --  107.75  77.00-150.00   56
 36  ω    126.00 175.00   0.50    0.28    --  107.75  45.00 -90.00   98
 37  ω     41.00 119.00   0.50    0.07    --   46.86  37.00-150.00  156
 38  ω     96.00 143.00   0.50    0.28    --  107.75  30.00 -30.00   94
 39  ω    145.00 177.00   0.50    0.28    --  107.75  30.00 -30.00   64
 40  ω     96.00 176.00   0.50    0.28    --  107.75  45.00  60.00  160
 41  ω    144.00 169.00   0.50    0.28    --  107.75  45.00  90.00   50
 42  ω    101.00 138.00   0.50    0.28    --  107.75  45.00  90.00   74
 43  ω   -106.00 -35.00   0.50    0.07    --  -46.86 162.00 122.00  142
 44  ω    -78.00 -40.00   0.50    0.07    --  -46.86 117.00 -27.00   76
 45  ω    -94.00 -69.00   0.50    0.28    --  -86.25 162.00 122.00   50
 46  ω    -73.00 -48.00   0.50    0.28    --  -86.25 117.00 -27.00   50
 47  ω   -142.00-113.00   0.50    0.28    --  -86.25 -30.00 -60.00   58
 48  ω   -119.00 -93.00   0.50    0.28    --  -86.25-117.00-115.00   52
 49  ω   -109.00 -84.00   0.50    0.07    --  -46.86-162.00  94.00   50
 50  ω   -118.00 -93.00   0.50    0.28    --  -86.25-162.00  94.00   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      -0.1614219000
_diffrn_orient_matrix_UB_12      -0.0682961000
_diffrn_orient_matrix_UB_13      0.0543916000
_diffrn_orient_matrix_UB_21      -0.1232802000
_diffrn_orient_matrix_UB_22      -0.0507857000
_diffrn_orient_matrix_UB_23      -0.1611323000
_diffrn_orient_matrix_UB_31      0.0459062000
_diffrn_orient_matrix_UB_32      -0.1650191000
_diffrn_orient_matrix_UB_33      -0.0256108000
_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                2215
_reflns_number_total             2488
_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 1.171.43.96a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_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         0.243
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.045
_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)+(0.0718P)²+0.0962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1060
_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 -0.29539(14) 0.56284(12) 0.06012(12) 0.0282(3) Uani 1 1 d . . . . .
O2 O -0.22585(14) 0.33285(12) 0.01703(12) 0.0274(3) Uani 1 1 d . . . . .
N9 N 0.30498(15) 0.87598(13) 0.40117(12) 0.0190(3) Uani 1 1 d . . . . .
N10 N 0.21858(15) 0.72945(13) 0.32656(13) 0.0198(3) Uani 1 1 d . . . . .
N11 N -0.05458(15) 0.80989(13) 0.26168(12) 0.0188(3) Uani 1 1 d . . . . .
N12 N 0.03372(15) 0.96172(13) 0.33858(12) 0.0179(2) Uani 1 1 d . . . . .
N13 N 0.30617(16) 1.14320(14) 0.47838(13) 0.0208(3) Uani 1 1 d . . . . .
H13A H 0.257(3) 1.224(2) 0.484(2) 0.029(5) Uiso 1 1 d . . . . .
H13B H 0.420(3) 1.157(2) 0.522(2) 0.031(5) Uiso 1 1 d . . . . .
N14 N -0.02379(16) 0.53504(14) 0.18110(14) 0.0239(3) Uani 1 1 d . . . . .
N15 N -0.18586(15) 0.48022(13) 0.08591(13) 0.0189(2) Uani 1 1 d . . . . .
C4 C 0.21137(17) 0.99347(15) 0.40400(14) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.03906(17) 0.69803(16) 0.25408(15) 0.0184(3) Uani 1 1 d . . . . .
N1 N 0.73869(15) 0.10811(13) 0.27682(12) 0.0188(3) Uani 1 1 d . . . . .
H1 H 0.849(3) 0.094(3) 0.309(2) 0.041(6) Uiso 1 1 d . . . . .
N2 N 0.70976(15) 0.26379(13) 0.30976(13) 0.0196(3) Uani 1 1 d . . . . .
N3 N 0.40216(15) 0.30805(13) 0.22202(12) 0.0186(3) Uani 1 1 d . . . . .
N4 N 0.27128(15) 0.04104(13) 0.11028(13) 0.0178(2) Uani 1 1 d . . . . .
N5 N 0.45842(15) 0.07352(13) 0.17466(12) 0.0169(2) Uani 1 1 d . . . . .
N6 N 0.42733(17) 0.47436(13) 0.27354(15) 0.0232(3) Uani 1 1 d . . . . .
H6A H 0.402(3) 0.514(2) 0.194(2) 0.038(5) Uiso 1 1 d . . . . .
H6B H 0.350(3) 0.496(2) 0.327(2) 0.034(5) Uiso 1 1 d . . . . .
N7 N 0.08530(16) 0.22354(15) 0.11117(14) 0.0225(3) Uani 1 1 d . . . . .
H7A H -0.006(3) 0.150(2) 0.055(2) 0.022(4) Uiso 1 1 d . . . . .
H7B H 0.079(3) 0.328(3) 0.136(2) 0.036(5) Uiso 1 1 d . . . . .
N8 N 0.57073(16) -0.16384(14) 0.14906(13) 0.0200(3) Uani 1 1 d . . . . .
H8A H 0.463(3) -0.229(2) 0.090(2) 0.024(4) Uiso 1 1 d . . . . .
H8B H 0.670(3) -0.204(2) 0.166(2) 0.032(5) Uiso 1 1 d . . . . .
C1 C 0.53731(18) 0.23200(15) 0.24396(14) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.24520(17) 0.18811(15) 0.14298(14) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.58877(17) -0.00801(16) 0.19648(14) 0.0170(3) Uani 1 1 d . . . . .
O3 O 0.85432(15) 0.58766(13) 0.53853(13) 0.0286(3) Uani 1 1 d . . . . .
H3A H 0.821(3) 0.495(3) 0.471(3) 0.051(6) Uiso 1 1 d . . . . .
H3B H 0.945(4) 0.580(3) 0.611(3) 0.064(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 N15 1.2430(15) . ?
O2 N15 1.2604(14) . ?
N9 N10 1.2945(16) . ?
N9 C4 1.3745(17) . ?
N10 C5 1.3675(16) . ?
N11 N12 1.3385(15) . ?
N11 C5 1.3330(17) . ?
N12 C4 1.3401(17) . ?
N13 H13A 0.87(2) . ?
N13 H13B 0.87(2) . ?
N13 C4 1.3310(17) . ?
N14 N15 1.3165(16) . ?
N14 C5 1.3861(17) . ?
N1 H1 0.89(2) . ?
N1 N2 1.4080(15) . ?
N1 C3 1.3455(17) . ?
N2 C1 1.3044(17) . ?
N3 N6 1.3959(15) . ?
N3 C1 1.3580(16) . ?
N3 C2 1.3926(16) . ?
N4 N5 1.4049(15) . ?
N4 C2 1.3270(17) . ?
N5 C1 1.3586(17) . ?
N5 C3 1.3598(16) . ?
N6 H6A 0.91(2) . ?
N6 H6B 0.89(2) . ?
N7 H7A 0.85(2) . ?
N7 H7B 0.91(2) . ?
N7 C2 1.3344(16) . ?
N8 H8A 0.91(2) . ?
N8 H8B 0.91(2) . ?
N8 C3 1.3137(17) . ?
O3 H3A 0.88(3) . ?
O3 H3B 0.90(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
N10 N9 C4 118.23(11) . . ?
N9 N10 C5 118.92(11) . . ?
C5 N11 N12 118.19(11) . . ?
N11 N12 C4 118.41(10) . . ?
H13A N13 H13B 120.9(18) . . ?
C4 N13 H13A 121.6(13) . . ?
C4 N13 H13B 117.4(13) . . ?
N15 N14 C5 119.66(11) . . ?
O1 N15 O2 120.07(11) . . ?
O1 N15 N14 124.90(11) . . ?
O2 N15 N14 115.03(11) . . ?
N12 C4 N9 122.90(12) . . ?
N13 C4 N9 116.38(12) . . ?
N13 C4 N12 120.71(12) . . ?
N10 C5 N14 108.73(11) . . ?
N11 C5 N10 123.21(12) . . ?
N11 C5 N14 128.00(12) . . ?
N2 N1 H1 119.7(14) . . ?
C3 N1 H1 126.4(14) . . ?
C3 N1 N2 113.82(11) . . ?
C1 N2 N1 100.56(10) . . ?
C1 N3 N6 123.77(11) . . ?
C1 N3 C2 106.22(10) . . ?
C2 N3 N6 130.01(11) . . ?
C2 N4 N5 101.00(10) . . ?
C1 N5 N4 113.46(10) . . ?
C1 N5 C3 107.41(11) . . ?
C3 N5 N4 139.02(11) . . ?
N3 N6 H6A 108.4(13) . . ?
N3 N6 H6B 110.3(13) . . ?
H6A N6 H6B 107.5(19) . . ?
H7A N7 H7B 120.4(18) . . ?
C2 N7 H7A 118.6(12) . . ?
C2 N7 H7B 120.0(14) . . ?
H8A N8 H8B 119.9(17) . . ?
C3 N8 H8A 120.1(11) . . ?
C3 N8 H8B 119.5(13) . . ?
N2 C1 N3 140.17(12) . . ?
N2 C1 N5 114.41(11) . . ?
N3 C1 N5 105.42(11) . . ?
N4 C2 N3 113.87(11) . . ?
N4 C2 N7 125.24(12) . . ?
N7 C2 N3 120.84(12) . . ?
N1 C3 N5 103.80(11) . . ?
N8 C3 N1 128.63(12) . . ?
N8 C3 N5 127.58(12) . . ?
H3A O3 H3B 106(2) . . ?

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
N13 H13A O3 0.87(2) 2.04(2) 2.8991(16) 169.8(17) 2_676 yes
N13 H13B N9 0.87(2) 2.21(2) 3.0595(16) 164.4(17) 2_676 yes
N1 H1 N12 0.89(2) 2.03(2) 2.8644(16) 154(2) 1_645 yes
N6 H6A O1 0.91(2) 2.28(2) 3.0456(18) 142.2(17) 2_565 yes
N6 H6B N10 0.89(2) 2.47(2) 3.0375(16) 122.4(16) . yes
N7 H7B N14 0.91(2) 2.12(2) 3.0019(17) 161.8(19) . yes
N8 H8A O2 0.91(2) 1.85(2) 2.7499(16) 169.7(17) 2 yes
N8 H8B O1 0.91(2) 2.17(2) 2.8381(15) 129.4(17) 1_645 yes
N8 H8B N11 0.91(2) 2.12(2) 2.9658(16) 154.6(17) 1_645 yes
O3 H3A N2 0.88(3) 2.15(3) 3.0178(15) 174(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
N9 N10 C5 N11 -3.1(2) . . . . ?
N9 N10 C5 N14 179.33(11) . . . . ?
N10 N9 C4 N12 2.99(19) . . . . ?
N10 N9 C4 N13 -178.17(11) . . . . ?
N11 N12 C4 N9 -2.99(19) . . . . ?
N11 N12 C4 N13 178.21(11) . . . . ?
N12 N11 C5 N10 3.12(19) . . . . ?
N12 N11 C5 N14 -179.85(12) . . . . ?
N15 N14 C5 N10 -170.05(12) . . . . ?
N15 N14 C5 N11 12.6(2) . . . . ?
C4 N9 N10 C5 0.07(18) . . . . ?
C5 N11 N12 C4 -0.05(18) . . . . ?
C5 N14 N15 O1 -4.0(2) . . . . ?
C5 N14 N15 O2 175.00(12) . . . . ?
N1 N2 C1 N3 178.75(16) . . . . ?
N1 N2 C1 N5 0.05(14) . . . . ?
N2 N1 C3 N5 0.65(14) . . . . ?
N2 N1 C3 N8 -179.56(12) . . . . ?
N4 N5 C1 N2 177.32(10) . . . . ?
N4 N5 C1 N3 -1.82(14) . . . . ?
N4 N5 C3 N1 -176.34(14) . . . . ?
N4 N5 C3 N8 3.9(3) . . . . ?
N5 N4 C2 N3 0.19(14) . . . . ?
N5 N4 C2 N7 -177.12(12) . . . . ?
N6 N3 C1 N2 2.5(3) . . . . ?
N6 N3 C1 N5 -178.70(11) . . . . ?
N6 N3 C2 N4 179.23(12) . . . . ?
N6 N3 C2 N7 -3.3(2) . . . . ?
C1 N3 C2 N4 -1.28(15) . . . . ?
C1 N3 C2 N7 176.16(12) . . . . ?
C1 N5 C3 N1 -0.57(13) . . . . ?
C1 N5 C3 N8 179.63(12) . . . . ?
C2 N3 C1 N2 -177.00(16) . . . . ?
C2 N3 C1 N5 1.78(13) . . . . ?
C2 N4 N5 C1 1.02(14) . . . . ?
C2 N4 N5 C3 176.62(15) . . . . ?
C3 N1 N2 C1 -0.44(14) . . . . ?
C3 N5 C1 N2 0.34(16) . . . . ?
C3 N5 C1 N3 -178.79(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 JS8664
_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 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.769
