# Electronic Supplementary Material (ESI) 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_js1023a
_database_code_depnum_ccdc_archive 'CCDC 2352179'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_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         'C4 H2 N8 O4'
_chemical_formula_sum            'C4 H2 N8 O4'
_chemical_formula_weight         226.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H2N8O4
_chemical_oxdiff_usercomment     TVK-0068-3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.62863(11)
_cell_length_b                   9.67955(12)
_cell_length_c                   9.75493(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.4845(12)
_cell_angle_gamma                90
_cell_volume                     813.238(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3796
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.5110
_cell_measurement_theta_min      4.4920
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.753
_exptl_absorpt_coefficient_mu    1.456
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.91a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 5 -1 0.0674
-4 -2 4 0.0907
2 4 -4 0.0653
5 -1 -3 0.1029
4 2 4 0.0067
-4 -2 -4 0.0371
2 -5 2 0.0674
-5 2 1 0.0709

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.046
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
-2.6114 5.4735 -0.7767 -0.1348 -0.5713 0.8090
-4.0148 -2.0591 4.1553 -0.1815 -0.7605 -0.6219
2.2505 4.3319 -3.9604 0.0930 0.3913 0.9153
4.8822 -1.0150 -3.2419 0.2308 0.9631 0.1284
3.6648 2.1226 3.9981 0.9969 -0.0251 0.0086
-3.6563 -1.9816 -4.0764 -0.9968 0.0252 0.0170
2.4954 -5.3120 1.6856 0.2238 0.4652 -0.8563
-5.1514 2.3180 1.1463 -0.4187 -0.8820 0.2113

_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.322
_diffrn_reflns_theta_min         6.448
_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 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -162.00-121.00   0.50    0.07    --  -91.75 -94.00-180.00   82
  2  ω    -26.00   3.00   0.50    0.05    --  -47.12  38.00-150.00   58
  3  ω    -47.00 -19.00   0.50    0.07    --  -91.75  38.00-150.00   56
  4  ω   -122.00 -96.00   0.50    0.07    --  -91.75 -38.00  54.00   52
  5  ω   -119.00 -35.00   0.50    0.05    --  -47.12 -38.00  54.00  168
  6  ω     45.00  88.00   0.50    0.05    --   47.12-125.00-120.00   86
  7  ω     72.00  97.00   0.50    0.07    --  113.25-125.00 -90.00   50
  8  ω     45.00  71.00   0.50    0.07    --  113.25-125.00   0.00   52
  9  ω     67.00  99.00   0.50    0.07    --  113.25 -94.00 -30.00   64
 10  ω     43.00  93.00   0.50    0.07    --  113.25 -94.00  30.00  100
 11  ω     45.00  71.00   0.50    0.07    --  113.25-125.00 120.00   52
 12  ω     77.00 102.00   0.50    0.07    --  113.25-125.00 120.00   50
 13  ω     63.00  94.00   0.50    0.07    --  113.25 -77.00 150.00   62
 14  ω     43.00  68.00   0.50    0.07    --  113.25 -61.00  90.00   50
 15  ω     43.00  69.00   0.50    0.07    --  113.25 -61.00 120.00   52
 16  ω     53.00  90.00   0.50    0.07    --  113.25 -77.00  90.00   74
 17  ω     44.00  84.00   0.50    0.07    --  113.25 -77.00  30.00   80
 18  ω     42.00  67.00   0.50    0.07    --  113.25 -61.00  30.00   50
 19  ω     42.00  67.00   0.50    0.07    --  113.25 -61.00   0.00   50
 20  ω     43.00  69.00   0.50    0.07    --  113.25 -61.00  60.00   52
 21  ω     43.00  68.00   0.50    0.07    --  113.25 -61.00 -30.00   50
 22  ω     42.00  67.00   0.50    0.07    --  113.25 -61.00 -60.00   50
 23  ω     51.00  92.00   0.50    0.07    --  113.25 -77.00 -90.00   82
 24  ω     42.00  67.00   0.50    0.07    --  113.25 -61.00 -90.00   50
 25  ω      8.00  45.00   0.50    0.05    --   47.12 -38.00  54.00   74
 26  ω     82.00 119.00   0.50    0.05    --   47.12  37.00 150.00   74
 27  ω    115.00 171.00   0.50    0.07    --  113.25  61.00 150.00  112
 28  ω    114.00 170.00   0.50    0.07    --  113.25  61.00 120.00  112
 29  ω     59.00 106.00   0.50    0.05    --   47.12  38.00-150.00   94
 30  ω    102.00 178.00   0.50    0.07    --  113.25  38.00-150.00  152
;
_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      0.1277078000
_diffrn_orient_matrix_UB_12      0.0512148000
_diffrn_orient_matrix_UB_13      0.1050974000
_diffrn_orient_matrix_UB_21      0.1252058000
_diffrn_orient_matrix_UB_22      -0.0574922000
_diffrn_orient_matrix_UB_23      -0.0905273000
_diffrn_orient_matrix_UB_31      0.0047174000
_diffrn_orient_matrix_UB_32      0.1392636000
_diffrn_orient_matrix_UB_33      -0.0761001000
_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                1590
_reflns_number_total             1741
_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 1.171.43.91a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_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         0.297
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.073
_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)+(0.0504P)²+0.2769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0916
_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 0.79196(13) 1.04269(11) 0.73045(11) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.58771(13) 0.92405(13) 0.77935(12) 0.0316(3) Uani 1 1 d . . . . .
O3 O 0.41976(12) 0.86887(11) 0.53270(11) 0.0253(3) Uani 1 1 d . . . . .
O13 O 0.42810(11) 0.66877(11) 0.43215(10) 0.0210(2) Uani 1 1 d . . . . .
N1 N 0.89552(12) 0.69449(10) 0.53405(10) 0.0117(2) Uani 1 1 d . . . . .
H1 H 0.986(2) 0.6482(19) 0.5289(18) 0.020(4) Uiso 1 1 d . . . . .
N2 N 0.89298(12) 0.79980(11) 0.62329(11) 0.0134(2) Uani 1 1 d . . . . .
N3 N 0.64605(13) 0.54255(11) 0.26390(11) 0.0142(2) Uani 1 1 d . . . . .
H3 H 0.572(2) 0.600(2) 0.231(2) 0.031(5) Uiso 1 1 d . . . . .
N4 N 0.67436(13) 0.42335(11) 0.19991(12) 0.0169(3) Uani 1 1 d . . . . .
N5 N 0.78269(13) 0.36091(11) 0.27432(11) 0.0160(2) Uani 1 1 d . . . . .
N6 N 0.82528(12) 0.43743(11) 0.38720(11) 0.0135(2) Uani 1 1 d . . . . .
N7 N 0.70419(13) 0.94436(12) 0.71658(12) 0.0192(3) Uani 1 1 d . . . . .
N8 N 0.48853(13) 0.76594(12) 0.49655(11) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.75469(14) 0.66370(12) 0.47589(12) 0.0113(3) Uani 1 1 d . . . . .
C2 C 0.65204(14) 0.75639(12) 0.53066(12) 0.0122(3) Uani 1 1 d . . . . .
C3 C 0.74573(15) 0.83739(13) 0.62106(12) 0.0131(3) Uani 1 1 d . . . . .
C4 C 0.73913(14) 0.55017(12) 0.37797(12) 0.0116(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N7 1.2187(17) . ?
O2 N7 1.2241(17) . ?
O3 N8 1.2225(15) . ?
O13 N8 1.2294(15) . ?
N1 H1 0.906(19) . ?
N1 N2 1.3415(14) . ?
N1 C1 1.3429(16) . ?
N2 C3 1.3206(17) . ?
N3 H3 0.89(2) . ?
N3 N4 1.3414(15) . ?
N3 C4 1.3342(16) . ?
N4 N5 1.2974(15) . ?
N5 N6 1.3590(14) . ?
N6 C4 1.3204(16) . ?
N7 C3 1.4524(16) . ?
N8 C2 1.4328(16) . ?
C1 C2 1.3901(17) . ?
C1 C4 1.4568(17) . ?
C2 C3 1.3998(17) . ?

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 H1 117.4(11) . . ?
N2 N1 C1 113.13(10) . . ?
C1 N1 H1 129.0(11) . . ?
C3 N2 N1 104.61(10) . . ?
N4 N3 H3 120.9(13) . . ?
C4 N3 H3 130.5(13) . . ?
C4 N3 N4 108.56(11) . . ?
N5 N4 N3 106.60(10) . . ?
N4 N5 N6 110.46(10) . . ?
C4 N6 N5 105.77(10) . . ?
O1 N7 O2 126.40(12) . . ?
O1 N7 C3 116.87(11) . . ?
O2 N7 C3 116.65(12) . . ?
O3 N8 O13 124.94(11) . . ?
O3 N8 C2 118.29(11) . . ?
O13 N8 C2 116.77(11) . . ?
N1 C1 C2 106.00(11) . . ?
N1 C1 C4 119.30(11) . . ?
C2 C1 C4 134.69(11) . . ?
C1 C2 N8 126.43(11) . . ?
C1 C2 C3 104.27(11) . . ?
C3 C2 N8 129.27(11) . . ?
N2 C3 N7 117.43(11) . . ?
N2 C3 C2 111.98(11) . . ?
C2 C3 N7 130.38(11) . . ?
N3 C4 C1 127.98(11) . . ?
N6 C4 N3 108.60(11) . . ?
N6 C4 C1 123.34(11) . . ?

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
N1 H1 N6 0.906(19) 1.960(19) 2.7928(15) 152.1(16) 3_766 yes
N3 H3 N2 0.89(2) 2.06(2) 2.9350(16) 167.9(18) 4_575 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
O1 N7 C3 N2 42.29(17) . . . . ?
O1 N7 C3 C2 -143.44(14) . . . . ?
O2 N7 C3 N2 -134.83(13) . . . . ?
O2 N7 C3 C2 39.44(19) . . . . ?
O3 N8 C2 C1 -165.91(12) . . . . ?
O3 N8 C2 C3 12.13(19) . . . . ?
O13 N8 C2 C1 13.92(18) . . . . ?
O13 N8 C2 C3 -168.04(12) . . . . ?
N1 N2 C3 N7 175.46(10) . . . . ?
N1 N2 C3 C2 0.17(14) . . . . ?
N1 C1 C2 N8 178.24(11) . . . . ?
N1 C1 C2 C3 -0.20(13) . . . . ?
N1 C1 C4 N3 -142.70(13) . . . . ?
N1 C1 C4 N6 33.78(17) . . . . ?
N2 N1 C1 C2 0.33(14) . . . . ?
N2 N1 C1 C4 -179.20(10) . . . . ?
N3 N4 N5 N6 0.41(14) . . . . ?
N4 N3 C4 N6 -0.23(14) . . . . ?
N4 N3 C4 C1 176.67(12) . . . . ?
N4 N5 N6 C4 -0.55(14) . . . . ?
N5 N6 C4 N3 0.46(13) . . . . ?
N5 N6 C4 C1 -176.61(11) . . . . ?
N8 C2 C3 N2 -178.36(12) . . . . ?
N8 C2 C3 N7 7.1(2) . . . . ?
C1 N1 N2 C3 -0.31(13) . . . . ?
C1 C2 C3 N2 0.02(14) . . . . ?
C1 C2 C3 N7 -174.50(13) . . . . ?
C2 C1 C4 N3 37.9(2) . . . . ?
C2 C1 C4 N6 -145.58(14) . . . . ?
C4 N3 N4 N5 -0.11(14) . . . . ?
C4 C1 C2 N8 -2.3(2) . . . . ?
C4 C1 C2 C3 179.22(13) . . . . ?

_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 TVK-0068-3
_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 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.866
####################################################################### 
# 
# 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_js324a
_database_code_depnum_ccdc_archive 'CCDC 2352181'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_audit_creation_date             2024-03-19
_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         'C4 H2 N9 O4, C2 H8 N'
_chemical_formula_sum            'C6 H10 N10 O4'
_chemical_formula_weight         286.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H3N9O4
_chemical_oxdiff_usercomment     TVK-0393-1
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                   6.0120(3)
_cell_length_b                   9.7746(3)
_cell_length_c                   9.9277(4)
_cell_angle_alpha                80.652(3)
_cell_angle_beta                 76.157(4)
_cell_angle_gamma                84.914(3)
_cell_volume                     558.18(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3540
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.1040
_cell_measurement_theta_min      4.6150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.106a (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    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.0661
2 0 -4 0.0553
-1 -6 -1 0.0114
1 6 1 0.0114
3 -3 3 0.0124
-3 3 -3 0.0124

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.023
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
-1.0007 0.9949 2.0008 0.4205 0.2061 -0.0944
2.4750 -0.4903 -3.8579 -0.8772 -0.4763 -0.0606
-0.8239 -6.2635 -0.8180 -0.0098 0.0010 0.9970
0.8239 6.2635 0.8180 0.0098 -0.0010 -0.9970
3.0900 -2.9684 2.5095 0.0701 -0.9235 0.3792
-3.0900 2.9684 -2.5095 -0.0701 0.9235 -0.3792

_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6256
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.364
_diffrn_reflns_theta_min         4.591
_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 0.998
_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     38.00  65.00   0.50    0.80    --  107.75-125.00-150.00   54
  2  ω     72.00 103.00   0.50    0.80    --  107.75-125.00-150.00   62
  3  ω     55.00 102.00   0.50    0.80    --  107.75 -94.00-150.00   94
  4  ω     55.00 100.00   0.50    0.80    --  107.75 -94.00-120.00   90
  5  ω     79.00 104.00   0.50    0.80    --  107.75 -94.00 -60.00   50
  6  ω     37.00  62.00   0.50    0.80    --  107.75 -94.00 -60.00   50
  7  ω     78.00 104.00   0.50    0.80    --  107.75 -94.00   0.00   52
  8  ω     38.00  89.00   0.50    0.80    --  107.75 -94.00  30.00  102
  9  ω     35.00 104.00   0.50    0.80    --  107.75 -94.00  60.00  138
 10  ω     36.00 101.00   0.50    0.80    --  107.75 -94.00  90.00  130
 11  ω     57.00 102.00   0.50    0.80    --  107.75 -94.00 120.00   90
 12  ω     77.00 103.00   0.50    0.80    --  107.75 -94.00 150.00   52
 13  ω    -27.00  28.00   0.50    0.20    --   47.36 -17.00  13.00  110
 14  ω     35.00  67.00   0.50    0.80    --  107.75 -61.00 -30.00   64
 15  ω     40.00  69.00   0.50    0.80    --  107.75 -61.00-180.00   58
 16  ω     73.00  98.00   0.50    0.80    --  107.75 -77.00-120.00   50
 17  ω     39.00  81.00   0.50    0.80    --  107.75 -77.00 -60.00   84
 18  ω     36.00  63.00   0.50    0.80    --  107.75 -61.00 -60.00   54
 19  ω     37.00  66.00   0.50    0.80    --  107.75 -61.00-120.00   58
 20  ω      0.00  33.00   0.50    0.20    --   47.36 -37.00 -30.00   66
 21  ω     39.00  67.00   0.50    0.80    --  107.75 -61.00 120.00   56
 22  ω     41.00  67.00   0.50    0.80    --  107.75 -61.00 150.00   52
 23  ω    110.00 175.00   0.50    0.80    --  107.75  77.00   0.00  130
 24  ω    107.00 152.00   0.50    0.80    --  107.75  61.00-120.00   90
 25  ω     97.00 152.00   0.50    0.80    --  107.75  45.00 -90.00  110
 26  ω     99.00 125.00   0.50    0.80    --  107.75  45.00 120.00   52
 27  ω    128.00 172.00   0.50    0.80    --  107.75  45.00 120.00   88
 28  ω     76.00 115.00   0.50    0.20    --   47.36  17.00-177.00   78
 29  ω     37.00  66.00   0.50    0.20    --   47.36  17.00-177.00   58
 30  ω    120.00 178.00   0.50    0.80    --  107.75  17.00-177.00  116
 31  ω    104.00 172.00   0.50    0.80    --  107.75  45.00  90.00  136
 32  ω    -30.00  28.00   0.50    0.20    --  -47.36  17.00-177.00  116
 33  ω    -70.00 -13.00   0.50    0.80    --  -86.25  61.00 -30.00  114
 34  ω    -68.00   6.00   0.50    0.20    --  -47.36  77.00 150.00  148
 35  ω    -72.00 -35.00   0.50    0.20    --  -47.36 -17.00  13.00   74
 36  ω   -123.00 -77.00   0.50    0.20    --  -47.36 -17.00  13.00   92
 37  ω   -161.00-126.00   0.50    0.80    --  -86.25 -17.00  13.00   70
 38  ω   -149.00-123.00   0.50    0.80    --  -86.25-125.00 -90.00   52
 39  ω   -119.00 -94.00   0.50    0.80    --  -86.25-125.00 -90.00   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      -0.1096923000
_diffrn_orient_matrix_UB_12      -0.0045844000
_diffrn_orient_matrix_UB_13      0.1575910000
_diffrn_orient_matrix_UB_21      -0.2376048000
_diffrn_orient_matrix_UB_22      0.0354709000
_diffrn_orient_matrix_UB_23      -0.0334897000
_diffrn_orient_matrix_UB_31      -0.0367481000
_diffrn_orient_matrix_UB_32      -0.1558955000
_diffrn_orient_matrix_UB_33      0.0119476000
_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                1870
_reflns_number_total             2274
_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 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.106a 64-bit (release 01-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (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         0.517
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.056
_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)+(0.0775P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1371
_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 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0913(3) 0.36901(15) 0.49010(16) 0.0392(4) Uani 1 1 d . . . . .
O2 O 0.2135(3) 0.16208(16) 0.44232(17) 0.0420(4) Uani 1 1 d . . . . .
O3 O 0.8606(2) 0.28330(14) 0.82159(16) 0.0368(4) Uani 1 1 d . . . . .
O4 O 0.7095(3) 0.14500(15) 0.72400(19) 0.0437(4) Uani 1 1 d . . . . .
N1 N 0.2829(3) 0.48523(17) 0.64239(19) 0.0337(4) Uani 1 1 d . . . . .
H1 H 0.183(5) 0.504(3) 0.606(3) 0.040(7) Uiso 1 1 d . . . . .
N2 N 0.3605(3) 0.57331(16) 0.71004(18) 0.0338(4) Uani 1 1 d . . . . .
N3 N 0.8079(3) 0.53355(18) 0.90565(18) 0.0336(4) Uani 1 1 d . . . . .
H3 H 0.877(6) 0.457(3) 0.909(3) 0.059(9) Uiso 1 1 d . . . . .
N4 N 0.8543(3) 0.63477(17) 0.96973(19) 0.0364(4) Uani 1 1 d . . . . .
N5 N 0.7140(3) 0.73950(17) 0.94370(19) 0.0390(4) Uani 1 1 d . . . . .
N6 N 0.5778(3) 0.70779(17) 0.8644(2) 0.0380(4) Uani 1 1 d . . . . .
N7 N 0.3673(3) 0.24595(17) 0.58774(18) 0.0338(4) Uani 1 1 d . . . . .
N8 N 0.2186(3) 0.26118(18) 0.50523(18) 0.0346(4) Uani 1 1 d . . . . .
N9 N 0.7163(3) 0.25892(16) 0.75839(18) 0.0325(4) Uani 1 1 d . . . . .
C1 C 0.3936(3) 0.35786(19) 0.6464(2) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.5569(3) 0.36660(19) 0.7256(2) 0.0315(4) Uani 1 1 d . . . . .
C3 C 0.5292(3) 0.50304(19) 0.7610(2) 0.0316(4) Uani 1 1 d . . . . .
C4 C 0.6389(3) 0.5782(2) 0.8410(2) 0.0325(4) Uani 1 1 d . . . . .
N10 N 0.3452(3) -0.04683(19) 0.7257(2) 0.0386(4) Uani 1 1 d . . . . .
H10A H 0.466(5) -0.121(3) 0.731(3) 0.052(7) Uiso 1 1 d . . . . .
H10B H 0.402(6) 0.039(3) 0.665(4) 0.063(9) Uiso 1 1 d . . . . .
C5 C 0.1755(4) -0.0988(2) 0.6654(3) 0.0411(5) Uani 1 1 d . . . . .
H5A H 0.118385 -0.185461 0.722752 0.062 Uiso 1 1 calc R U . . .
H5B H 0.246901 -0.116172 0.569701 0.062 Uiso 1 1 calc R U . . .
H5C H 0.047464 -0.029664 0.663469 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2480(5) -0.0154(2) 0.8696(3) 0.0479(6) Uani 1 1 d . . . . .
H6A H 0.183922 -0.099066 0.929651 0.072 Uiso 1 1 calc R U . . .
H6B H 0.126570 0.058214 0.867684 0.072 Uiso 1 1 calc R U . . .
H6C H 0.369151 0.015428 0.906674 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N8 1.257(2) . ?
O2 N8 1.241(2) . ?
O3 N9 1.245(2) . ?
O4 N9 1.223(2) . ?
N1 H1 0.77(3) . ?
N1 N2 1.349(3) . ?
N1 C1 1.358(2) . ?
N2 C3 1.328(2) . ?
N3 H3 0.83(3) . ?
N3 N4 1.341(3) . ?
N3 C4 1.333(3) . ?
N4 N5 1.301(2) . ?
N5 N6 1.349(3) . ?
N6 C4 1.329(3) . ?
N7 N8 1.334(2) . ?
N7 C1 1.358(3) . ?
N9 C2 1.411(2) . ?
C1 C2 1.412(3) . ?
C2 C3 1.419(3) . ?
C3 C4 1.460(3) . ?
N10 H10A 0.98(3) . ?
N10 H10B 0.99(3) . ?
N10 C5 1.463(3) . ?
N10 C6 1.479(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 H1 123(2) . . ?
N2 N1 C1 114.32(17) . . ?
C1 N1 H1 122(2) . . ?
C3 N2 N1 105.71(16) . . ?
N4 N3 H3 123(2) . . ?
C4 N3 H3 128(2) . . ?
C4 N3 N4 109.39(16) . . ?
N5 N4 N3 106.09(17) . . ?
N4 N5 N6 110.59(17) . . ?
C4 N6 N5 106.41(16) . . ?
N8 N7 C1 117.19(16) . . ?
O1 N8 N7 122.81(18) . . ?
O2 N8 O1 121.24(17) . . ?
O2 N8 N7 115.95(16) . . ?
O3 N9 C2 118.60(16) . . ?
O4 N9 O3 121.93(15) . . ?
O4 N9 C2 119.47(17) . . ?
N1 C1 C2 103.61(17) . . ?
N7 C1 N1 130.72(19) . . ?
N7 C1 C2 125.64(16) . . ?
N9 C2 C1 125.21(18) . . ?
N9 C2 C3 128.35(19) . . ?
C1 C2 C3 106.44(16) . . ?
N2 C3 C2 109.92(18) . . ?
N2 C3 C4 115.54(17) . . ?
C2 C3 C4 134.53(17) . . ?
N3 C4 C3 128.62(18) . . ?
N6 C4 N3 107.52(19) . . ?
N6 C4 C3 123.84(17) . . ?
H10A N10 H10B 113(3) . . ?
C5 N10 H10A 107.1(16) . . ?
C5 N10 H10B 107.8(19) . . ?
C5 N10 C6 112.50(19) . . ?
C6 N10 H10A 107.5(17) . . ?
C6 N10 H10B 108.8(19) . . ?
N10 C5 H5A 109.5 . . ?
N10 C5 H5B 109.5 . . ?
N10 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N10 C6 H6A 109.5 . . ?
N10 C6 H6B 109.5 . . ?
N10 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 N9 C2 C1 175.52(18) . . . . ?
O3 N9 C2 C3 -3.2(3) . . . . ?
O4 N9 C2 C1 -4.3(3) . . . . ?
O4 N9 C2 C3 177.0(2) . . . . ?
N1 N2 C3 C2 -0.6(2) . . . . ?
N1 N2 C3 C4 -179.28(17) . . . . ?
N1 C1 C2 N9 -179.61(19) . . . . ?
N1 C1 C2 C3 -0.7(2) . . . . ?
N2 N1 C1 N7 -177.88(19) . . . . ?
N2 N1 C1 C2 0.4(2) . . . . ?
N2 C3 C4 N3 178.7(2) . . . . ?
N2 C3 C4 N6 0.5(3) . . . . ?
N3 N4 N5 N6 0.1(2) . . . . ?
N4 N3 C4 N6 -0.1(2) . . . . ?
N4 N3 C4 C3 -178.58(19) . . . . ?
N4 N5 N6 C4 -0.2(2) . . . . ?
N5 N6 C4 N3 0.2(2) . . . . ?
N5 N6 C4 C3 178.74(19) . . . . ?
N7 C1 C2 N9 -1.3(3) . . . . ?
N7 C1 C2 C3 177.68(18) . . . . ?
N8 N7 C1 N1 4.2(3) . . . . ?
N8 N7 C1 C2 -173.73(18) . . . . ?
N9 C2 C3 N2 179.71(19) . . . . ?
N9 C2 C3 C4 -2.0(4) . . . . ?
C1 N1 N2 C3 0.1(2) . . . . ?
C1 N7 N8 O1 -6.1(3) . . . . ?
C1 N7 N8 O2 173.39(17) . . . . ?
C1 C2 C3 N2 0.8(2) . . . . ?
C1 C2 C3 C4 179.2(2) . . . . ?
C2 C3 C4 N3 0.4(4) . . . . ?
C2 C3 C4 N6 -177.8(2) . . . . ?
C4 N3 N4 N5 0.0(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 TVK-0393-1
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.702
_vrf_PLAT430_js324a              
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.71 Ang.  
RESPONSE: We have seen in these small compounds that they will pack with some 
relatively short O---O distances that get flagged by cifcheck routine.
;
####################################################################### 
# 
# 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_js324b
_database_code_depnum_ccdc_archive 'CCDC 2352182'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_audit_creation_date             2024-03-19
_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         'C4 N8 O4, 2(H4 N)'
_chemical_formula_sum            'C4 H8 N10 O4'
_chemical_formula_weight         260.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H8N10O4
_chemical_oxdiff_usercomment     TVK-0466
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.04522(10)
_cell_length_b                   9.82848(11)
_cell_length_c                   12.90621(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.3666(11)
_cell_angle_gamma                90
_cell_volume                     1009.66(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7311
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6640
_cell_measurement_theta_min      3.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.312
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.696
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -1 0.0604
0 -2 1 0.0064
-5 -1 -2 0.0833
5 3 -2 0.1187
1 -3 7 0.0464
0 3 -7 0.0619
0 5 5 0.0516
1 4 -7 0.0728
-3 -1 -6 0.0751
5 0 -3 0.1084
3 -5 0 0.0530

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.067
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
-0.0041 2.0010 -1.0084 0.0122 -0.2067 0.2649
0.0041 -2.0010 1.0084 -0.0122 0.2067 -0.2649
-4.6815 -0.7928 -2.4138 -0.9928 0.0232 0.1133
4.6673 2.7066 -2.1844 0.8617 -0.0212 0.5037
1.1321 -2.5388 7.1253 0.4226 -0.0083 -0.9061
-0.1738 2.9742 -7.2857 -0.2377 0.0038 0.9708
-0.0090 5.0081 4.9906 0.3221 -0.9312 -0.0891
0.9976 4.0007 -7.0103 0.0195 -0.0923 1.0432
-2.9960 -1.0048 -6.0044 -0.8212 0.3256 0.4781
4.9972 0.0045 -3.0045 0.8215 0.3929 0.3687
3.0040 -5.0020 -0.0009 0.4336 0.7923 -0.3694

_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11895
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.635
_diffrn_reflns_theta_min         5.681
_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 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00 -12.00   0.50    0.05    --  -47.36  79.00 163.00   60
  2  ω    -61.00 -31.00   0.50    0.05    --  -47.36  57.00 -60.00   60
  3  ω    -31.00  27.00   0.50    0.05    --  -47.36  19.00 -90.00  116
  4  ω    -23.00  25.00   0.50    0.05    --  -47.36  57.00 -60.00   96
  5  ω    -16.00  28.00   0.50    0.05    --   47.36 -19.00  90.00   88
  6  ω    -19.00  25.00   0.50    0.05    --   47.36 -19.00  30.00   88
  7  ω    -17.00  16.00   0.50    0.05    --   47.36 -79.00  38.00   66
  8  ω     43.00  72.00   0.50    0.05    --   47.36-125.00 -60.00   58
  9  ω     36.00  61.00   0.50    0.05    --  107.75 -94.00  60.00   50
 10  ω     39.00  67.00   0.50    0.05    --  107.75 -94.00  90.00   56
 11  ω     37.00 100.00   0.50    0.05    --  107.75 -94.00 150.00  126
 12  ω     77.00 102.00   0.50    0.05    --  107.75 -94.00  90.00   50
 13  ω     74.00 102.00   0.50    0.05    --  107.75 -94.00  60.00   56
 14  ω     47.00  72.00   0.50    0.05    --  107.75 -79.00  38.00   50
 15  ω     42.00  69.00   0.50    0.05    --  107.75 -77.00 150.00   54
 16  ω     38.00  67.00   0.50    0.05    --  107.75 -77.00  90.00   58
 17  ω     37.00  69.00   0.50    0.05    --  107.75 -77.00  60.00   64
 18  ω     42.00  67.00   0.50    0.05    --  107.75 -61.00  30.00   50
 19  ω     39.00  67.00   0.50    0.05    --  107.75 -61.00 -30.00   56
 20  ω     35.00  65.00   0.50    0.05    --  107.75 -61.00-120.00   60
 21  ω     35.00  69.00   0.50    0.05    --  107.75 -61.00-180.00   68
 22  ω     94.00 156.00   0.50    0.05    --  107.75  15.00 -90.00  124
 23  ω    130.00 178.00   0.50    0.05    --  107.75  77.00-120.00   96
 24  ω    143.00 178.00   0.50    0.05    --  107.75  61.00   0.00   70
 25  ω    111.00 176.00   0.50    0.05    --  107.75  77.00  30.00  130
 26  ω    111.00 143.00   0.50    0.05    --  107.75  61.00  90.00   64
 27  ω    153.00 178.00   0.50    0.05    --  107.75  61.00  90.00   50
 28  ω    149.00 174.00   0.50    0.05    --  107.75  79.00 163.00   50
 29  ω    103.00 140.00   0.50    0.05    --  107.75  79.00 163.00   74
 30  ω    114.00 140.00   0.50    0.05    --  107.75  61.00   0.00   52
 31  ω    108.00 162.00   0.50    0.05    --  107.75  61.00 -60.00  108
 32  ω    115.00 142.00   0.50    0.05    --  107.75  45.00-150.00   54
 33  ω    145.00 177.00   0.50    0.05    --  107.75  45.00-150.00   64
 34  ω     96.00 165.00   0.50    0.05    --  107.75  30.00 -60.00  138
 35  ω     96.00 177.00   0.50    0.05    --  107.75  30.00  90.00  162
 36  ω     98.00 149.00   0.50    0.05    --  107.75  30.00 150.00  102
 37  ω     97.00 123.00   0.50    0.05    --  107.75  30.00 120.00   52
 38  ω    -39.00 -14.00   0.50    0.05    --  -86.25  30.00-180.00   50
 39  ω    -36.00 -11.00   0.50    0.05    --  -86.25  30.00   0.00   50
 40  ω   -104.00 -78.00   0.50    0.05    --  -86.25  79.00 163.00   52
 41  ω    -74.00 -35.00   0.50    0.05    --  -86.25  79.00 163.00   78
 42  ω   -158.00 -81.00   0.50    0.05    --  -86.25 -79.00  38.00  154
 43  ω   -119.00 -36.00   0.50    0.05    --  -47.36 -37.00-120.00  166
;
_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      0.1876784000
_diffrn_orient_matrix_UB_12      0.0260161000
_diffrn_orient_matrix_UB_13      0.0387660000
_diffrn_orient_matrix_UB_21      0.0456336000
_diffrn_orient_matrix_UB_22      -0.1309740000
_diffrn_orient_matrix_UB_23      -0.0550787000
_diffrn_orient_matrix_UB_31      0.0135287000
_diffrn_orient_matrix_UB_32      0.0819865000
_diffrn_orient_matrix_UB_33      -0.1001014000
_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                1987
_reflns_number_total             2117
_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 43.106a 64-bit (release 01-02-2024))'
_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         0.324
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.065
_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)+(0.0461P)²+0.4852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0889
_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 0.82198(13) 0.29707(11) 0.39595(8) 0.0250(2) Uani 1 1 d . . . . .
O2 O 0.62432(13) 0.39205(10) 0.46909(8) 0.0243(2) Uani 1 1 d . . . . .
O3 O 0.59140(13) 0.36347(10) 0.67805(9) 0.0279(3) Uani 1 1 d . . . . .
O4 O 0.38311(12) 0.22352(10) 0.66982(8) 0.0235(2) Uani 1 1 d . . . . .
N1 N 0.77658(14) 0.05964(11) 0.49348(8) 0.0167(2) Uani 1 1 d . . . . .
N2 N 0.73792(14) -0.03739(11) 0.56042(8) 0.0164(2) Uani 1 1 d . . . . .
N3 N 0.54544(13) -0.01157(11) 0.79932(8) 0.0155(2) Uani 1 1 d . . . . .
N4 N 0.49824(14) -0.12085(11) 0.85117(8) 0.0178(2) Uani 1 1 d . . . . .
N5 N 0.50671(14) -0.22984(12) 0.79291(9) 0.0192(2) Uani 1 1 d . . . . .
N6 N 0.55902(15) -0.19674(11) 0.70199(8) 0.0183(2) Uani 1 1 d . . . . .
N7 N 0.71904(14) 0.29614(11) 0.45760(8) 0.0175(2) Uani 1 1 d . . . . .
N8 N 0.52521(13) 0.25308(11) 0.65340(8) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.70698(15) 0.17563(13) 0.51877(9) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.61714(15) 0.15538(12) 0.60204(9) 0.0136(2) Uani 1 1 d . . . . .
C3 C 0.64007(15) 0.01809(12) 0.62638(9) 0.0140(3) Uani 1 1 d . . . . .
C4 C 0.58139(15) -0.06207(13) 0.70878(9) 0.0138(3) Uani 1 1 d . . . . .
N10 N 0.14876(15) 0.01394(12) 0.70956(9) 0.0174(2) Uani 1 1 d . . . . .
H10A H 0.091(2) 0.095(2) 0.7040(14) 0.027(4) Uiso 1 1 d . . . . .
H10B H 0.088(3) -0.047(2) 0.7394(16) 0.041(5) Uiso 1 1 d . . . . .
H10C H 0.162(2) -0.018(2) 0.6420(16) 0.036(5) Uiso 1 1 d . . . . .
H10D H 0.247(3) 0.028(2) 0.7483(16) 0.034(5) Uiso 1 1 d . . . . .
N9 N 0.69716(16) 0.16962(12) 0.96211(9) 0.0186(2) Uani 1 1 d . . . . .
H9A H 0.638(3) 0.157(2) 1.0176(16) 0.035(5) Uiso 1 1 d . . . . .
H9B H 0.639(2) 0.1286(19) 0.9050(15) 0.028(5) Uiso 1 1 d . . . . .
H9C H 0.706(2) 0.259(2) 0.9532(14) 0.028(5) Uiso 1 1 d . . . . .
H9D H 0.798(3) 0.132(2) 0.9708(16) 0.040(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 N7 1.2292(15) . ?
O2 N7 1.2346(15) . ?
O3 N8 1.2299(15) . ?
O4 N8 1.2275(14) . ?
N1 N2 1.3531(15) . ?
N1 C1 1.3315(17) . ?
N2 C3 1.3552(15) . ?
N3 N4 1.3489(15) . ?
N3 C4 1.3394(16) . ?
N4 N5 1.3162(16) . ?
N5 N6 1.3430(15) . ?
N6 C4 1.3370(17) . ?
N7 C1 1.4345(16) . ?
N8 C2 1.4321(15) . ?
C1 C2 1.3940(16) . ?
C2 C3 1.3917(17) . ?
C3 C4 1.4563(17) . ?
N10 H10A 0.92(2) . ?
N10 H10B 0.89(2) . ?
N10 H10C 0.94(2) . ?
N10 H10D 0.88(2) . ?
N9 H9A 0.93(2) . ?
N9 H9B 0.91(2) . ?
N9 H9C 0.89(2) . ?
N9 H9D 0.88(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 107.63(10) . . ?
N1 N2 C3 109.03(10) . . ?
C4 N3 N4 104.47(10) . . ?
N5 N4 N3 108.84(10) . . ?
N4 N5 N6 110.54(10) . . ?
C4 N6 N5 103.82(10) . . ?
O1 N7 O2 123.91(11) . . ?
O1 N7 C1 117.92(11) . . ?
O2 N7 C1 118.17(11) . . ?
O3 N8 C2 118.54(10) . . ?
O4 N8 O3 122.91(11) . . ?
O4 N8 C2 118.55(10) . . ?
N1 C1 N7 120.50(11) . . ?
N1 C1 C2 110.52(11) . . ?
C2 C1 N7 128.78(11) . . ?
C1 C2 N8 128.45(11) . . ?
C3 C2 N8 127.31(11) . . ?
C3 C2 C1 104.23(11) . . ?
N2 C3 C2 108.57(11) . . ?
N2 C3 C4 121.38(11) . . ?
C2 C3 C4 130.01(11) . . ?
N3 C4 C3 124.81(11) . . ?
N6 C4 N3 112.33(11) . . ?
N6 C4 C3 122.86(11) . . ?
H10A N10 H10B 108.2(17) . . ?
H10A N10 H10C 109.6(16) . . ?
H10A N10 H10D 108.3(17) . . ?
H10B N10 H10C 108.5(18) . . ?
H10B N10 H10D 111.0(18) . . ?
H10C N10 H10D 111.2(17) . . ?
H9A N9 H9B 107.6(17) . . ?
H9A N9 H9C 107.2(17) . . ?
H9A N9 H9D 114.3(18) . . ?
H9B N9 H9C 112.0(17) . . ?
H9B N9 H9D 105.7(18) . . ?
H9C N9 H9D 110.1(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
N10 H10A N5 0.92(2) 1.90(2) 2.8100(16) 172.5(17) 2_556 yes
N10 H10B O3 0.89(2) 2.11(2) 2.9732(15) 162.6(19) 2_546 yes
N10 H10C N1 0.94(2) 1.93(2) 2.8650(15) 169.3(18) 3_656 yes
N9 H9B N3 0.91(2) 2.01(2) 2.8861(16) 162.7(17) . yes
N9 H9C N2 0.89(2) 2.07(2) 2.9485(16) 172.0(17) 2_656 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
O1 N7 C1 N1 -14.54(17) . . . . ?
O1 N7 C1 C2 171.18(12) . . . . ?
O2 N7 C1 N1 164.66(11) . . . . ?
O2 N7 C1 C2 -9.62(19) . . . . ?
O3 N8 C2 C1 -46.08(18) . . . . ?
O3 N8 C2 C3 132.19(14) . . . . ?
O4 N8 C2 C1 133.11(13) . . . . ?
O4 N8 C2 C3 -48.61(18) . . . . ?
N1 N2 C3 C2 -0.87(14) . . . . ?
N1 N2 C3 C4 -178.79(11) . . . . ?
N1 C1 C2 N8 179.50(12) . . . . ?
N1 C1 C2 C3 0.92(14) . . . . ?
N2 N1 C1 N7 -176.71(10) . . . . ?
N2 N1 C1 C2 -1.47(14) . . . . ?
N2 C3 C4 N3 151.98(12) . . . . ?
N2 C3 C4 N6 -27.34(18) . . . . ?
N3 N4 N5 N6 0.01(14) . . . . ?
N4 N3 C4 N6 -0.04(14) . . . . ?
N4 N3 C4 C3 -179.43(11) . . . . ?
N4 N5 N6 C4 -0.03(14) . . . . ?
N5 N6 C4 N3 0.05(14) . . . . ?
N5 N6 C4 C3 179.44(11) . . . . ?
N7 C1 C2 N8 -5.8(2) . . . . ?
N7 C1 C2 C3 175.66(12) . . . . ?
N8 C2 C3 N2 -178.62(11) . . . . ?
N8 C2 C3 C4 -0.9(2) . . . . ?
C1 N1 N2 C3 1.44(14) . . . . ?
C1 C2 C3 N2 -0.02(14) . . . . ?
C1 C2 C3 C4 177.67(12) . . . . ?
C2 C3 C4 N3 -25.5(2) . . . . ?
C2 C3 C4 N6 155.23(13) . . . . ?
C4 N3 N4 N5 0.02(13) . . . . ?

_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 TVK-0466
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.801
