# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_js122m
_database_code_depnum_ccdc_archive 'CCDC 2160643'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 N8 O2'
_chemical_formula_sum            'C4 H4 N8 O2'
_chemical_formula_weight         196.15
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x+1/2, z+1/4'
'-x, -y, z'
'y, -x+1/2, z+1/4'
'-x, y, z+1/2'
'x, -y, z+1/2'
'-y+1/2, -x, z+1/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1, z+3/4'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1, z+3/4'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
'-y+1, -x+1/2, z+3/4'
'y+1, x+1/2, z+3/4'

_cell_length_a                   10.60713(10)
_cell_length_b                   10.60713(10)
_cell_length_c                   12.1560(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1367.69(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4012
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.0360
_cell_measurement_theta_min      8.3390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.377
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -5 0 0.0742
0 -7 1 0.0961
-3 6 -1 0.0647
3 6 0 0.0682
0 1 -8 0.0216
0 -1 8 0.0257
6 2 -3 0.0675
5 -5 -1 0.1017
1 -7 -2 0.0933

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.049
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6016
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.324
_diffrn_reflns_theta_min         8.358
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  61.00   0.50    0.06    --  107.19 -77.00-120.00   50
  2  ω     68.00 103.00   0.50    0.06    --  107.19 -77.00-120.00   70
  3  ω     43.00  84.00   0.50    0.06    --  107.19 -77.00-180.00   82
  4  ω     37.00  64.00   0.50    0.06    --  107.19 -57.00  60.00   54
  5  ω     35.00  65.00   0.50    0.06    --  107.19 -57.00 120.00   60
  6  ω     35.00  60.00   0.50    0.06    --  107.19 -57.00  90.00   50
  7  ω     37.00  62.00   0.50    0.06    --  107.19 -57.00-120.00   50
  8  ω    108.00 134.00   0.50    0.06    --  107.19 125.00 120.00   52
  9  ω    152.00 178.00   0.50    0.06    --  107.19 125.00 120.00   52
 10  ω    -27.00  18.00   0.50    0.05    --  -47.62  19.00  60.00   90
 11  ω    -60.00 -23.00   0.50    0.06    --  -91.75  57.00  60.00   74
 12  ω    -59.00 -21.00   0.50    0.06    --  -91.75  57.00  30.00   76
 13  ω    -68.00   0.00   0.50    0.05    --  -47.62  77.00-180.00  136
 14  ω    -56.00 -25.00   0.50    0.06    --  -91.75  57.00-150.00   62
 15  ω   -164.00 -83.00   0.50    0.06    --  -91.75 -19.00 -90.00  162
 16  ω   -163.00-127.00   0.50    0.06    --  -91.75 -57.00-180.00   72
 17  ω   -161.00-132.00   0.50    0.06    --  -91.75 -57.00 -90.00   58
 18  ω   -157.00-127.00   0.50    0.06    --  -91.75 -57.00 -30.00   60
 19  ω   -161.00-126.00   0.50    0.06    --  -91.75 -77.00  30.00   70
 20  ω   -153.00-127.00   0.50    0.06    --  -91.75 -57.00 120.00   52
 21  ω   -158.00-130.00   0.50    0.06    --  -91.75 -57.00  60.00   56
 22  ω   -155.00-127.00   0.50    0.06    --  -91.75 -57.00  30.00   56
 23  ω   -165.00-115.00   0.50    0.06    --  -91.75 -37.00-120.00  100
 24  ω   -163.00-122.00   0.50    0.06    --  -91.75 -99.00-150.00   82
 25  ω   -113.00 -80.00   0.50    0.05    --  -47.62 -19.00  30.00   66
 26  ω    -74.00 -37.00   0.50    0.05    --  -47.62 -19.00  30.00   74
 27  ω    -82.00 -36.00   0.50    0.05    --  -47.62 -19.00  60.00   92
 28  ω   -119.00 -93.00   0.50    0.05    --  -47.62 -19.00  60.00   52
 29  ω     41.00 104.00   0.50    0.06    --  107.19 -99.00 150.00  126
 30  ω     79.00 104.00   0.50    0.06    --  107.19 -99.00  90.00   50
 31  ω     71.00  96.00   0.50    0.06    --  107.19 -99.00  60.00   50
 32  ω     35.00  71.00   0.50    0.06    --  107.19 -99.00  90.00   72
 33  ω     15.00  46.00   0.50    0.05    --   47.62 -99.00 -60.00   62
 34  ω     49.00  81.00   0.50    0.05    --   47.62 -99.00 -60.00   64
 35  ω     43.00  69.00   0.50    0.06    --  107.19-125.00 -90.00   52
 36  ω     76.00 108.00   0.50    0.06    --  107.19-125.00 -90.00   64
 37  ω     77.00 102.00   0.50    0.06    --  107.19 -99.00 -30.00   50
 38  ω     36.00  72.00   0.50    0.06    --  107.19 -99.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                683
_reflns_number_total             703
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.00018(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         703
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.168
_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)+(0.0582P)²+1.8053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -1.11282(19) -0.75224(19) -1.1951(4) 0.0205(5) Uani 1 1 d . . . . .
H1 H -1.146327 -0.817865 -1.169795 0.031 Uiso 1 1 calc GR . . . .
N1 N -1.1948(2) -0.6611(2) -1.1952(5) 0.0164(6) Uani 1 1 d . . . . .
N2 N -1.3203(2) -0.6847(2) -1.1944(4) 0.0186(6) Uani 1 1 d . . . . .
N3 N -1.3782(2) -0.5769(2) -1.1944(4) 0.0190(6) Uani 1 1 d . . . . .
N4 N -1.2907(2) -0.4857(2) -1.1956(7) 0.0160(6) Uani 1 1 d . . . . .
C1 C -1.1741(3) -0.5365(3) -1.1943(5) 0.0160(7) Uani 1 1 d . . . . .
C2 C -1.0558(3) -0.4704(2) -1.1946(6) 0.0164(6) Uani 1 1 d . . . . .
H2 H -1.056815 -0.380798 -1.194831 0.020 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0137(10) 0.0114(9) 0.0366(12) 0.0006(17) -0.0001(15) 0.0013(8)
N1 0.0137(12) 0.0115(11) 0.0239(12) -0.001(2) 0.0011(17) -0.0013(8)
N2 0.0107(13) 0.0199(13) 0.0252(14) -0.001(2) -0.0018(17) -0.0005(9)
N3 0.0182(13) 0.0126(11) 0.0262(12) 0.0022(17) 0.0011(19) -0.0021(9)
N4 0.0129(10) 0.0117(11) 0.0233(11) 0.002(2) -0.001(3) 0.0001(9)
C1 0.0152(14) 0.0138(13) 0.0190(12) 0.000(3) 0.003(3) 0.0004(9)
C2 0.0182(13) 0.0115(13) 0.0196(11) -0.002(3) 0.002(3) -0.0015(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 N1 1.300(3) . ?
N1 N2 1.354(4) . ?
N1 C1 1.340(4) . ?
N2 N3 1.298(3) . ?
N3 N4 1.341(3) . ?
N4 C1 1.350(3) . ?
C1 C2 1.437(4) . ?
C2 C2 1.341(5) 3_345 ?
C2 H2 0.9500 . ?

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
N1 O1 H1 109.5 . . ?
O1 N1 N2 121.3(2) . . ?
O1 N1 C1 128.6(2) . . ?
C1 N1 N2 110.1(2) . . ?
N3 N2 N1 107.6(2) . . ?
N2 N3 N4 107.9(2) . . ?
N3 N4 C1 110.3(2) . . ?
N1 C1 N4 104.1(2) . . ?
N1 C1 C2 128.7(2) . . ?
N4 C1 C2 127.3(2) . . ?
C1 C2 H2 118.6 . . ?
C2 C2 C1 122.8(3) 3_345 . ?
C2 C2 H2 118.6 3_345 . ?

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
C2 H2 O1 0.95 2.29 2.962(3) 127.5 3_345 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 N1 N2 N3 179.9(6) . . . . ?
O1 N1 C1 N4 179.6(6) . . . . ?
O1 N1 C1 C2 1.0(9) . . . . ?
N1 N2 N3 N4 0.2(7) . . . . ?
N1 C1 C2 C2 -0.8(7) . . . 3_345 ?
N2 N1 C1 N4 -1.4(6) . . . . ?
N2 N1 C1 C2 180.0(5) . . . . ?
N2 N3 N4 C1 -1.1(9) . . . . ?
N3 N4 C1 N1 1.6(8) . . . . ?
N3 N4 C1 C2 -179.8(5) . . . . ?
N4 C1 C2 C2 -179.1(5) . . . 3_345 ?
C1 N1 N2 N3 0.8(6) . . . . ?

_shelx_res_file                  
;
TITL JS122M in I41cd #110
    js122m.res
    created by SHELXL-2018/3 at 15:04:32 on 28-Feb-2022
REM reset to I41cd #110
CELL 1.54184 10.60713 10.60713 12.15599 90 90 90
ZERR 8 0.0001 0.0001 0.00024 0 0 0
LATT -2
SYMM -Y,0.5+X,0.25+Z
SYMM -X,-Y,+Z
SYMM +Y,0.5-X,0.25+Z
SYMM -X,+Y,0.5+Z
SYMM +X,-Y,0.5+Z
SYMM 0.5-Y,-X,0.25+Z
SYMM 0.5+Y,+X,0.25+Z
SFAC C H N O
UNIT 32 32 64 16
EQIV $1 -2-X,-1-Y,+Z

L.S. 10
PLAN  5
TEMP -173
HTAB C2 O1_$1
CONF
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\js122m.hkl">
REM </olex2.extras>

WGHT    0.058200    1.805300
EXTI    0.000181
FVAR       1.97048
O1    4   -1.112819   -0.752240   -1.195112    11.00000    0.01367    0.01136 =
         0.03658    0.00059   -0.00008    0.00128
AFIX 147
H1    2   -1.146327   -0.817865   -1.169795    11.00000   -1.50000
AFIX   0
N1    3   -1.194786   -0.661117   -1.195170    11.00000    0.01369    0.01154 =
         0.02387   -0.00077    0.00110   -0.00135
N2    3   -1.320251   -0.684680   -1.194380    11.00000    0.01071    0.01989 =
         0.02524   -0.00120   -0.00183   -0.00052
N3    3   -1.378208   -0.576882   -1.194439    11.00000    0.01820    0.01264 =
         0.02624    0.00223    0.00113   -0.00208
N4    3   -1.290747   -0.485661   -1.195628    11.00000    0.01294    0.01165 =
         0.02335    0.00151   -0.00079    0.00011
C1    1   -1.174055   -0.536457   -1.194269    11.00000    0.01524    0.01376 =
         0.01901   -0.00019    0.00337    0.00042
C2    1   -1.055839   -0.470354   -1.194602    11.00000    0.01818    0.01153 =
         0.01958   -0.00152    0.00200   -0.00147
AFIX  43
H2    2   -1.056815   -0.380798   -1.194831    11.00000   -1.20000
AFIX   0
HKLF 4




REM  JS122M in I41cd #110
REM wR2 = 0.1064, GooF = S = 1.169, Restrained GooF = 1.168 for all data
REM R1 = 0.0378 for 683 Fo > 4sig(Fo) and 0.0384 for all 703 data
REM 66 parameters refined using 1 restraints

END

WGHT      0.0582      1.8048

REM Highest difference peak  0.548,  deepest hole -0.314,  1-sigma level  0.067
Q1    1  -1.3091 -0.4143 -1.1947  11.00000  0.05    0.55
Q2    1  -1.2388 -0.4922 -1.1947  11.00000  0.05    0.29
Q3    1  -1.3565 -0.7507 -1.1920  11.00000  0.05    0.26
Q4    1  -1.1700 -0.5771 -1.1954  11.00000  0.05    0.23
Q5    1  -1.3012 -0.8240 -1.1953  11.00000  0.05    0.22
;
_shelx_res_checksum              98255
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_js122h
_database_code_depnum_ccdc_archive 'CCDC 2160645'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-02-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_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, 2(H4 N O)'
_chemical_formula_sum            'C4 H10 N10 O2'
_chemical_formula_weight         230.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H10N10O2
_chemical_oxdiff_usercomment     JS234
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                   4.3728(2)
_cell_length_b                   7.3072(4)
_cell_length_c                   8.3883(4)
_cell_angle_alpha                66.474(5)
_cell_angle_beta                 81.732(4)
_cell_angle_gamma                79.997(4)
_cell_volume                     241.19(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9640
_cell_measurement_theta_min      5.7600
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 4 0.0113
-2 0 -4 0.0115
2 1 -2 0.0569
-2 -2 2 0.0724
-1 4 1 0.0423
0 -4 -4 0.0348
0 4 4 0.0408
-2 0 2 0.0552

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.025
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
1.7493 0.0610 4.1740 -0.9757 -0.0769 0.2051
-1.6791 -0.0712 -4.2658 0.9818 0.0774 -0.1734
2.2978 1.3260 -1.9096 0.1263 0.3521 0.9274
-2.0683 -2.1326 1.7420 -0.1870 -0.5238 -0.8310
-1.0831 3.9379 0.7878 0.2967 0.8395 -0.4553
-0.0337 -4.1416 -4.1594 0.4400 -0.8094 0.3890
0.0609 4.1559 4.1550 -0.4418 0.8128 -0.3797
-1.9996 0.0004 2.0027 -0.0855 -0.0610 -0.8449

_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2089
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.203
_diffrn_reflns_theta_min         5.772
_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 0.995
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    106.00 132.00   0.50    0.08    --  107.19  86.00-113.00   52
  2  ω    140.00 167.00   0.50    0.08    --  107.19  86.00-113.00   54
  3  ω    126.00 178.00   0.50    0.08    --  107.19  77.00  90.00  104
  4  ω    142.00 170.00   0.50    0.08    --  107.19  77.00 120.00   56
  5  ω     69.00  97.00   0.50    0.08    --  107.19 -86.00 128.00   56
  6  ω     70.00 104.00   0.50    0.08    --  107.19 -99.00  90.00   68
  7  ω     36.00  66.00   0.50    0.08    --  107.19 -99.00  30.00   60
  8  ω     37.00  63.00   0.50    0.08    --  107.19 -99.00  90.00   52
  9  ω     70.00  97.00   0.50    0.08    --  107.19 -99.00  30.00   54
 10  ω     39.00  73.00   0.50    0.05    --   47.62 -86.00 128.00   68
 11  ω    -16.00  12.00   0.50    0.05    --   47.62 -86.00 128.00   56
 12  ω     77.00 103.00   0.50    0.08    --  107.19 -99.00   0.00   52
 13  ω     39.00 102.00   0.50    0.08    --  107.19 -99.00 -90.00  126
 14  ω     45.00  90.00   0.50    0.08    --  107.19 -99.00-150.00   90
 15  ω     45.00  93.00   0.50    0.08    --  107.19 -77.00 -90.00   96
 16  ω     37.00  62.00   0.50    0.08    --  107.19 -57.00 -90.00   50
 17  ω     38.00  63.00   0.50    0.08    --  107.19 -57.00   0.00   50
 18  ω    -27.00  16.00   0.50    0.05    --   47.62 -19.00-180.00   86
 19  ω     39.00  64.00   0.50    0.08    --  107.19 -57.00  60.00   50
 20  ω     35.00  61.00   0.50    0.08    --  107.19 -57.00 120.00   52
 21  ω     36.00  62.00   0.50    0.08    --  107.19 -57.00 150.00   52
 22  ω    -42.00  -6.00   0.50    0.05    --  -47.62  37.00  60.00   72
 23  ω     -3.00  24.00   0.50    0.05    --  -47.62  37.00  60.00   54
 24  ω    -27.00  11.00   0.50    0.05    --  -47.62  19.00 -30.00   76
 25  ω    -23.00  27.00   0.50    0.05    --  -47.62  19.00-180.00  100
 26  ω    -80.00 -54.00   0.50    0.08    --  -91.75  86.00-113.00   52
 27  ω    -39.00 -13.00   0.50    0.05    --  -47.62  86.00-113.00   52
 28  ω   -163.00-129.00   0.50    0.08    --  -91.75 -77.00 -30.00   68
 29  ω   -162.00-129.00   0.50    0.08    --  -91.75 -57.00   0.00   66
 30  ω   -152.00-126.00   0.50    0.08    --  -91.75 -77.00  30.00   52
 31  ω   -163.00-121.00   0.50    0.08    --  -91.75 -37.00-150.00   84
 32  ω   -162.00-137.00   0.50    0.08    --  -91.75 -57.00-120.00   50
 33  ω   -161.00-133.00   0.50    0.08    --  -91.75 -57.00 -90.00   56
 34  ω   -161.00-136.00   0.50    0.08    --  -91.75 -77.00  90.00   50
 35  ω   -159.00-130.00   0.50    0.08    --  -91.75 -77.00 120.00   58
 36  ω   -134.00 -99.00   0.50    0.08    --  -91.75 -86.00 128.00   70
;
_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      -0.1355321000
_diffrn_orient_matrix_UB_12      0.0736790000
_diffrn_orient_matrix_UB_13      -0.1780405000
_diffrn_orient_matrix_UB_21      0.0062602000
_diffrn_orient_matrix_UB_22      0.2197475000
_diffrn_orient_matrix_UB_23      -0.0242650000
_diffrn_orient_matrix_UB_31      0.3323378000
_diffrn_orient_matrix_UB_32      -0.0061918000
_diffrn_orient_matrix_UB_33      -0.0900557000
_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                861
_reflns_number_total             947
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.291
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.094
_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)+(0.0536P)²+0.0565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2)
;
_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
N1 N 0.3448(2) 0.28533(17) 0.30022(15) 0.0125(3) Uani 1 1 d . . . . .
N2 N 0.5773(2) 0.34259(17) 0.17535(15) 0.0132(3) Uani 1 1 d . . . . .
N3 N 0.6760(2) 0.20034(17) 0.11529(15) 0.0133(3) Uani 1 1 d . . . . .
N4 N 0.5103(2) 0.04437(17) 0.20076(15) 0.0124(3) Uani 1 1 d . . . . .
C1 C 0.3097(3) 0.1002(2) 0.31444(17) 0.0115(3) Uani 1 1 d . . . . .
C2 C 0.0907(3) -0.0267(2) 0.43952(18) 0.0124(3) Uani 1 1 d . . . . .
H2 H 0.076147 -0.152734 0.434999 0.015 Uiso 1 1 calc R U . . .
O1 O -0.0281(2) 0.60998(16) 0.32213(13) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.097(5) 0.502(4) 0.319(3) 0.041(6) Uiso 1 1 d . . . . .
N5 N -0.1694(3) 0.69011(18) 0.16193(15) 0.0135(3) Uani 1 1 d . . . . .
H5A H -0.308(4) 0.805(3) 0.166(2) 0.022(4) Uiso 1 1 d . . . . .
H5B H -0.022(5) 0.730(3) 0.070(3) 0.022(5) Uiso 1 1 d . . . . .
H5C H -0.270(5) 0.593(3) 0.154(3) 0.027(5) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0127(5) 0.0115(6) 0.0126(6) -0.0039(5) -0.0002(4) -0.0018(4)
N2 0.0131(5) 0.0115(6) 0.0138(6) -0.0039(5) -0.0002(4) -0.0012(4)
N3 0.0141(6) 0.0114(6) 0.0133(6) -0.0039(5) -0.0002(4) -0.0015(4)
N4 0.0130(5) 0.0111(6) 0.0126(6) -0.0041(5) 0.0002(4) -0.0023(4)
C1 0.0112(6) 0.0113(7) 0.0118(6) -0.0041(5) -0.0029(5) 0.0000(5)
C2 0.0127(6) 0.0111(6) 0.0132(6) -0.0038(5) -0.0019(5) -0.0023(5)
O1 0.0266(6) 0.0146(5) 0.0167(5) -0.0083(4) -0.0082(4) 0.0058(4)
N5 0.0154(6) 0.0119(6) 0.0130(6) -0.0053(5) -0.0006(5) -0.0010(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3407(16) . ?
N1 C1 1.3440(17) . ?
N2 N3 1.3116(16) . ?
N3 N4 1.3504(16) . ?
N4 C1 1.3382(18) . ?
C1 C2 1.4561(19) . ?
C2 C2 1.337(3) 2_556 ?
C2 H2 0.9500 . ?
O1 H1 0.89(3) . ?
O1 N5 1.4197(15) . ?
N5 H5A 0.96(2) . ?
N5 H5B 0.91(2) . ?
N5 H5C 0.92(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 105.16(11) . . ?
N3 N2 N1 109.65(11) . . ?
N2 N3 N4 109.28(10) . . ?
C1 N4 N3 105.07(11) . . ?
N1 C1 C2 125.13(12) . . ?
N4 C1 N1 110.84(12) . . ?
N4 C1 C2 124.01(12) . . ?
C1 C2 H2 118.6 . . ?
C2 C2 C1 122.76(16) 2_556 . ?
C2 C2 H2 118.6 2_556 . ?
N5 O1 H1 104.1(15) . . ?
O1 N5 H5A 104.5(11) . . ?
O1 N5 H5B 110.4(12) . . ?
O1 N5 H5C 109.2(13) . . ?
H5A N5 H5B 109.7(16) . . ?
H5A N5 H5C 113.3(17) . . ?
H5B N5 H5C 109.7(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
O1 H1 N1 0.89(3) 1.80(3) 2.6905(15) 177(2) . yes
N5 H5A N4 0.96(2) 1.90(2) 2.8374(16) 164.2(17) 1_465 yes
N5 H5B N3 0.91(2) 1.98(2) 2.8938(17) 175.0(17) 2_665 yes
N5 H5C N2 0.92(2) 1.99(2) 2.8983(17) 167.4(18) 1_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 -0.34(14) . . . . ?
N1 C1 C2 C2 -3.2(2) . . . 2_556 ?
N2 N1 C1 N4 -0.84(14) . . . . ?
N2 N1 C1 C2 177.43(12) . . . . ?
N2 N3 N4 C1 -0.18(14) . . . . ?
N3 N4 C1 N1 0.64(14) . . . . ?
N3 N4 C1 C2 -177.65(12) . . . . ?
N4 C1 C2 C2 174.80(15) . . . 2_556 ?
C1 N1 N2 N3 0.71(14) . . . . ?

_shelx_res_file                  
;
TITL js122h_a.res in P-1
    js122h.res
    created by SHELXL-2018/3 at 10:50:23 on 02-Feb-2022
REM Old TITL JS122H in P-1
REM SHELXT solution in P-1: R1 0.099, Rweak 0.006, Alpha 0.020
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 N4
CELL 1.54184 4.3728 7.3072 8.3883 66.474 81.732 79.997
ZERR 1 0.0002 0.0004 0.0004 0.005 0.004 0.004
LATT 1
SFAC C H N O
UNIT 4 10 10 2
EQIV $1 -1+X,+Y,+Z
EQIV $2 1-X,1-Y,-Z
EQIV $3 -1+X,1+Y,+Z

L.S. 7
PLAN  5
SIZE 0.025 0.085 0.136
TEMP -173.15(10)
CONF
HTAB O1 N1
HTAB N5 N2_$1
HTAB N5 N3_$2
HTAB N5 N4_$3
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\JS122H.hkl">
REM </olex2.extras>

WGHT    0.053600    0.056500
FVAR      20.81612
N1    3    0.344818    0.285330    0.300216    11.00000    0.01273    0.01145 =
         0.01257   -0.00392   -0.00015   -0.00177
N2    3    0.577333    0.342587    0.175353    11.00000    0.01310    0.01146 =
         0.01381   -0.00394   -0.00025   -0.00121
N3    3    0.676041    0.200336    0.115285    11.00000    0.01409    0.01144 =
         0.01334   -0.00394   -0.00023   -0.00149
N4    3    0.510283    0.044367    0.200757    11.00000    0.01305    0.01107 =
         0.01255   -0.00413    0.00017   -0.00233
C1    1    0.309708    0.100180    0.314442    11.00000    0.01124    0.01126 =
         0.01184   -0.00407   -0.00285    0.00001
C2    1    0.090732   -0.026708    0.439515    11.00000    0.01273    0.01107 =
         0.01315   -0.00380   -0.00193   -0.00235
AFIX  43
H2    2    0.076147   -0.152734    0.434999    11.00000   -1.20000
AFIX   0

O1    4   -0.028121    0.609975    0.322135    11.00000    0.02655    0.01463 =
         0.01670   -0.00831   -0.00822    0.00581
H1    2    0.097093    0.501994    0.318673    11.00000    0.04083
N5    3   -0.169446    0.690107    0.161928    11.00000    0.01543    0.01188 =
         0.01303   -0.00527   -0.00057   -0.00102
H5A   2   -0.308361    0.805430    0.166087    11.00000    0.02203
H5B   2   -0.022349    0.729550    0.069946    11.00000    0.02233
H5C   2   -0.269945    0.593242    0.154290    11.00000    0.02652
HKLF 4




REM  js122h_a.res in P-1
REM wR2 = 0.0976, GooF = S = 1.094, Restrained GooF = 1.094 for all data
REM R1 = 0.0359 for 861 Fo > 4sig(Fo) and 0.0386 for all 947 data
REM 89 parameters refined using 0 restraints

END

WGHT      0.0536      0.0565

REM Highest difference peak  0.291,  deepest hole -0.271,  1-sigma level  0.059
Q1    1   0.1989  0.0408  0.3773  11.00000  0.05    0.29
Q2    1  -0.0612  0.0106  0.4621  11.00000  0.05    0.24
Q3    1   0.8461  0.1974  0.0671  11.00000  0.05    0.21
Q4    1   0.4199  0.3353  0.2143  11.00000  0.05    0.18
Q5    1   0.7386  0.2158  0.0080  11.00000  0.05    0.17
;
_shelx_res_checksum              88506
_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 JS234
_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 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.917
####################################################################### 
# 
# 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_js122e
_database_code_depnum_ccdc_archive 'CCDC 2160644'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-01-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H N4 O, H4 N O'
_chemical_formula_sum            'C2 H5 N5 O2'
_chemical_formula_weight         131.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H10N10O4
_chemical_oxdiff_usercomment     JS225
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.9233(2)
_cell_length_b                   10.6988(3)
_cell_length_c                   7.0551(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.465(3)
_cell_angle_gamma                90
_cell_volume                     522.10(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2055
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2800
_cell_measurement_theta_min      6.3910
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             272
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0417
0 -1 0 0.0492
0 -1 1 0.0474
0 1 -1 0.0294
-1 0 0 0.0120
1 0 0 0.0200
0 1 1 0.0289
0 -1 -1 0.0289

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.032
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
0.0007 0.9996 0.0013 -0.0861 0.1151 -0.0070
-0.0006 -1.0000 0.0002 0.0864 -0.1150 0.0071
-0.0004 -0.9978 0.9993 0.2534 0.0138 0.0637
0.0004 0.9978 -0.9993 -0.2534 -0.0138 -0.0637
-0.9992 0.0025 -0.0017 -0.0603 -0.0320 0.2118
0.9992 -0.0025 0.0017 0.0603 0.0320 -0.2118
0.0011 1.0029 0.9992 0.0806 0.2439 0.0495
-0.0011 -1.0029 -0.9992 -0.0806 -0.2439 -0.0495

_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2902
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.915
_diffrn_reflns_theta_min         6.399
_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 0.989
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  61.00   0.50    0.81    --  107.19 -57.00-120.00   52
  2  ω     37.00  62.00   0.50    0.81    --  107.19 -57.00  90.00   50
  3  ω     35.00  60.00   0.50    0.81    --  107.19 -57.00 120.00   50
  4  ω    -23.00  41.00   0.50    0.20    --   47.37 -37.00   0.00  128
  5  ω    -26.00  26.00   0.50    0.20    --  -47.37  19.00 120.00  104
  6  ω    -56.00 -16.00   0.50    0.20    --  -47.37 128.00 164.00   80
  7  ω   -162.00-134.00   0.50    0.81    --  -91.75 -57.00 -30.00   56
  8  ω   -162.00-136.00   0.50    0.81    --  -91.75 -77.00 -60.00   52
  9  ω   -157.00-127.00   0.50    0.81    --  -91.75 -57.00  30.00   60
 10  ω     -3.00  23.00   0.50    0.20    --  -47.37  19.00-180.00   52
 11  ω   -160.00-117.00   0.50    0.81    --  -91.75 -37.00-180.00   86
 12  ω   -157.00-127.00   0.50    0.81    --  -91.75 -77.00-180.00   60
 13  ω   -117.00 -75.00   0.50    0.20    --  -47.37-141.00 -81.00   84
 14  ω   -137.00 -65.00   0.50    0.81    --  -91.75-141.00 -81.00  144
 15  ω   -134.00-108.00   0.50    0.81    --  -91.75-128.00  89.00   52
 16  ω   -162.00-116.00   0.50    0.81    --  -91.75-125.00 150.00   92
 17  ω     42.00  68.00   0.50    0.81    --  107.19 -99.00 120.00   52
 18  ω     71.00 103.00   0.50    0.81    --  107.19 -99.00 120.00   64
 19  ω     73.00  98.00   0.50    0.81    --  107.19-128.00  89.00   50
 20  ω     39.00  94.00   0.50    0.81    --  107.19 -99.00  90.00  110
 21  ω     48.00  74.00   0.50    0.20    --   47.37-128.00  89.00   52
 22  ω     74.00  99.00   0.50    0.20    --   47.37-141.00 -81.00   50
 23  ω     66.00 118.00   0.50    0.81    --  107.19-141.00 -81.00  104
;
_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      0.0598420000
_diffrn_orient_matrix_UB_12      -0.0863814000
_diffrn_orient_matrix_UB_13      0.1673015000
_diffrn_orient_matrix_UB_21      0.0321307000
_diffrn_orient_matrix_UB_22      0.1149935000
_diffrn_orient_matrix_UB_23      0.1286791000
_diffrn_orient_matrix_UB_31      -0.2121381000
_diffrn_orient_matrix_UB_32      -0.0069480000
_diffrn_orient_matrix_UB_33      0.0567103000
_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                914
_reflns_number_total             1010
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0365
_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)+(0.0553P)²+0.2362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1006
_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     direct
_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 0.86887(15) 0.59515(10) 0.67616(15) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.67875(18) 0.61366(12) 0.65286(18) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.60275(19) 0.66752(12) 0.49607(18) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.41586(19) 0.66938(12) 0.51851(18) 0.0225(3) Uani 1 1 d . . . . .
N4 N 0.37054(19) 0.61797(12) 0.68545(18) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.5716(2) 0.52469(14) 0.9527(2) 0.0208(3) Uani 1 1 d . . . . .
H1 H 0.700(3) 0.5275(17) 1.004(3) 0.020(4) Uiso 1 1 d . . . . .
C2 C 0.5379(2) 0.58335(13) 0.7697(2) 0.0194(4) Uani 1 1 d . . . . .
O2 O 0.97249(17) 0.37454(11) 0.80649(16) 0.0253(3) Uani 1 1 d . . . . .
H2 H 0.938(4) 0.453(3) 0.760(4) 0.057(7) Uiso 1 1 d . . . . .
N5 N 0.9589(2) 0.29606(13) 0.64426(18) 0.0212(3) Uani 1 1 d . . . . .
H5A H 1.020(3) 0.222(2) 0.686(3) 0.038(6) Uiso 1 1 d . . . . .
H5B H 0.830(3) 0.2845(19) 0.612(3) 0.026(5) Uiso 1 1 d . . . . .
H5C H 1.022(3) 0.331(2) 0.548(3) 0.037(6) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0205(6) 0.0197(6) 0.0241(6) 0.0006(4) 0.0017(4) -0.0001(4)
N1 0.0214(7) 0.0158(6) 0.0197(6) 0.0003(5) 0.0011(5) 0.0005(4)
N2 0.0275(7) 0.0183(7) 0.0203(7) 0.0022(5) 0.0002(5) 0.0004(5)
N3 0.0249(7) 0.0208(7) 0.0216(7) 0.0019(5) -0.0005(5) -0.0001(5)
N4 0.0256(7) 0.0186(7) 0.0219(7) 0.0007(5) 0.0007(5) -0.0002(5)
C1 0.0229(8) 0.0179(7) 0.0216(8) 0.0001(6) 0.0013(6) 0.0003(6)
C2 0.0234(8) 0.0141(7) 0.0208(8) -0.0009(6) 0.0025(5) -0.0011(5)
O2 0.0350(7) 0.0189(6) 0.0219(6) -0.0007(4) -0.0001(4) 0.0038(4)
N5 0.0243(7) 0.0199(7) 0.0194(6) 0.0008(5) 0.0020(5) 0.0008(5)

_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 N1 1.3342(17) . ?
N1 N2 1.3351(18) . ?
N1 C2 1.3435(19) . ?
N2 N3 1.3104(19) . ?
N3 N4 1.3490(18) . ?
N4 C2 1.332(2) . ?
C1 C1 1.328(3) 3_667 ?
C1 H1 0.942(19) . ?
C1 C2 1.446(2) . ?
O2 H2 0.93(3) . ?
O2 N5 1.4194(17) . ?
N5 H5A 0.94(3) . ?
N5 H5B 0.92(2) . ?
N5 H5C 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 N2 121.18(12) . . ?
O1 N1 C2 128.83(13) . . ?
N2 N1 C2 109.99(13) . . ?
N3 N2 N1 105.22(12) . . ?
N2 N3 N4 111.54(12) . . ?
C2 N4 N3 105.81(12) . . ?
C1 C1 H1 122.1(11) 3_667 . ?
C1 C1 C2 121.75(19) 3_667 . ?
C2 C1 H1 116.1(11) . . ?
N1 C2 C1 124.01(14) . . ?
N4 C2 N1 107.44(13) . . ?
N4 C2 C1 128.56(13) . . ?
N5 O2 H2 104.0(17) . . ?
O2 N5 H5A 103.5(14) . . ?
O2 N5 H5B 108.1(13) . . ?
O2 N5 H5C 110.4(14) . . ?
H5A N5 H5B 112.7(18) . . ?
H5A N5 H5C 110.6(18) . . ?
H5B N5 H5C 111.2(19) . . ?

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
O2 H2 O1 0.93(3) 1.69(3) 2.6219(15) 178(2) . yes
N5 H5A O1 0.94(3) 1.82(3) 2.7418(18) 166(2) 2_746 yes
N5 H5B N3 0.92(2) 1.96(2) 2.8161(19) 153.6(18) 3_666 yes
N5 H5C O1 0.90(2) 1.95(2) 2.8493(17) 174(2) 3_766 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 N1 N2 N3 179.11(12) . . . . ?
O1 N1 C2 N4 -178.89(13) . . . . ?
O1 N1 C2 C1 1.5(2) . . . . ?
N1 N2 N3 N4 -0.07(16) . . . . ?
N2 N1 C2 N4 0.27(16) . . . . ?
N2 N1 C2 C1 -179.33(13) . . . . ?
N2 N3 N4 C2 0.24(16) . . . . ?
N3 N4 C2 N1 -0.30(16) . . . . ?
N3 N4 C2 C1 179.27(14) . . . . ?
C1 C1 C2 N1 -167.11(18) 3_667 . . . ?
C1 C1 C2 N4 13.4(3) 3_667 . . . ?
C2 N1 N2 N3 -0.12(16) . . . . ?

_shelx_res_file                  
;
TITL JS122E in P21/c #14
    js122e.res
    created by SHELXL-2018/3 at 10:44:14 on 25-Jan-2022
REM reset to P21/c #14
CELL 1.54184 6.923273 10.698847 7.055108 90 92.4651 90
ZERR 4 0.000199 0.000345 0.000223 0 0.0026 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 8 20 20 8
EQIV $1 2-X,1-Y,1-Z
EQIV $2 2-X,-0.5+Y,1.5-Z
EQIV $3 1-X,1-Y,1-Z

L.S. 12
PLAN  5
SIZE 0.032 0.058 0.094
TEMP -173.15(10)
CONF
HTAB O2 O1
HTAB N5 O1_$1
HTAB N5 O1_$2
HTAB N5 N3_$3
MORE -1
BOND $H
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\JS122E.hkl">
REM </olex2.extras>

WGHT    0.055300    0.236200
FVAR      11.59192
O1    4    0.868870    0.595152    0.676162    11.00000    0.02048    0.01970 =
         0.02407    0.00063    0.00172   -0.00005
N1    3    0.678748    0.613655    0.652859    11.00000    0.02145    0.01584 =
         0.01972    0.00034    0.00109    0.00053
N2    3    0.602748    0.667518    0.496073    11.00000    0.02755    0.01826 =
         0.02029    0.00218    0.00023    0.00039
N3    3    0.415855    0.669375    0.518511    11.00000    0.02490    0.02083 =
         0.02158    0.00191   -0.00049   -0.00005
N4    3    0.370539    0.617968    0.685446    11.00000    0.02562    0.01858 =
         0.02188    0.00074    0.00073   -0.00023
C1    1    0.571573    0.524688    0.952714    11.00000    0.02292    0.01790 =
         0.02156    0.00011    0.00132    0.00027
H1    2    0.699535    0.527499    1.003686    11.00000    0.01975
C2    1    0.537875    0.583353    0.769692    11.00000    0.02339    0.01413 =
         0.02080   -0.00086    0.00249   -0.00110
O2    4    0.972495    0.374542    0.806490    11.00000    0.03499    0.01892 =
         0.02187   -0.00073   -0.00006    0.00378
H2    2    0.938053    0.453310    0.759583    11.00000    0.05745
N5    3    0.958896    0.296062    0.644260    11.00000    0.02429    0.01992 =
         0.01938    0.00080    0.00201    0.00076
H5A   2    1.020309    0.222096    0.685702    11.00000    0.03787
H5B   2    0.829965    0.284524    0.611605    11.00000    0.02596
H5C   2    1.021863    0.330556    0.547912    11.00000    0.03746
HKLF 4




REM  JS122E in P21/c #14
REM wR2 = 0.1006, GooF = S = 1.056, Restrained GooF = 1.056 for all data
REM R1 = 0.0365 for 914 Fo > 4sig(Fo) and 0.0401 for all 1010 data
REM 102 parameters refined using 0 restraints

END

WGHT      0.0553      0.2362

REM Highest difference peak  0.456,  deepest hole -0.194,  1-sigma level  0.056
Q1    1   0.2332  0.5863  0.6955  11.00000  0.05    0.46
Q2    1   0.5557  0.5570  0.8672  11.00000  0.05    0.24
Q3    1   0.6123  0.6094  0.7375  11.00000  0.05    0.23
Q4    1   0.3230  0.6710  0.4327  11.00000  0.05    0.22
Q5    1   0.3759  0.6297  0.6222  11.00000  0.05    0.20
;
_shelx_res_checksum              90978
_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 JS225
_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 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.804
####################################################################### 
# 
# 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_js122k
_database_code_depnum_ccdc_archive 'CCDC 2160646'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 N8, 2(H4 N O)'
_chemical_formula_sum            'C4 H12 N10 O2'
_chemical_formula_weight         232.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           46
_space_group_name_H-M_alt        'I m a 2'
_space_group_name_Hall           'I 2 -2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y, z'
'-x+1/2, y, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'
'-x+1, y+1/2, z+1/2'

_cell_length_a                   7.45690(10)
_cell_length_b                   17.0704(2)
_cell_length_c                   8.04400(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1023.94(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5404
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.0410
_cell_measurement_theta_min      5.1750
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.066
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5541
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.305
_diffrn_reflns_theta_min         5.182
_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 0.994
_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     39.00  64.00   0.50    0.40    --  107.19 -57.00 -90.00   50
  2  ω     38.00  63.00   0.50    0.40    --  107.19 -57.00  60.00   50
  3  ω     36.00  65.00   0.50    0.40    --  107.19 -57.00 120.00   58
  4  ω    132.00 178.00   0.50    0.40    --  107.19  57.00 120.00   92
  5  ω    124.00 178.00   0.50    0.40    --  107.19 125.00 -60.00  108
  6  ω    -22.00  28.00   0.50    0.10    --  -47.62  19.00 120.00  100
  7  ω    -20.00  18.00   0.50    0.10    --  -47.62  19.00-120.00   76
  8  ω    -20.00  26.00   0.50    0.10    --  -47.62  19.00-180.00   92
  9  ω     -8.00  26.00   0.50    0.10    --  -47.62  37.00   0.00   68
 10  ω    -61.00   5.00   0.50    0.10    --  -47.62  57.00 150.00  132
 11  ω    -66.00 -21.00   0.50    0.40    --  -91.75  57.00  30.00   90
 12  ω    -80.00 -33.00   0.50    0.40    --  -91.75 125.00-180.00   94
 13  ω    -77.00 -46.00   0.50    0.10    --  -47.62 125.00 -60.00   62
 14  ω    -82.00 -57.00   0.50    0.40    --  -91.75 125.00   0.00   50
 15  ω    -92.00 -20.00   0.50    0.40    --  -91.75  77.00  30.00  144
 16  ω   -166.00 -89.00   0.50    0.40    --  -91.75 -19.00-120.00  154
 17  ω   -163.00-120.00   0.50    0.40    --  -91.75 -37.00-150.00   86
 18  ω   -161.00-126.00   0.50    0.40    --  -91.75 -77.00-180.00   70
 19  ω   -163.00-137.00   0.50    0.40    --  -91.75 -57.00-120.00   52
 20  ω   -159.00-133.00   0.50    0.40    --  -91.75 -77.00 -90.00   52
 21  ω   -158.00-132.00   0.50    0.40    --  -91.75 -57.00 -30.00   52
 22  ω   -165.00-115.00   0.50    0.40    --  -91.75 -37.00   0.00  100
 23  ω   -139.00-114.00   0.50    0.40    --  -91.75 -37.00 -60.00   50
 24  ω   -165.00-126.00   0.50    0.40    --  -91.75 -37.00 -90.00   78
 25  ω   -122.00 -41.00   0.50    0.10    --  -47.62 -19.00-180.00  162
 26  ω   -138.00-112.00   0.50    0.40    --  -91.75-125.00 -30.00   52
 27  ω   -153.00-127.00   0.50    0.40    --  -91.75 -99.00 -30.00   52
 28  ω   -160.00-120.00   0.50    0.40    --  -91.75 -99.00  30.00   80
 29  ω     42.00  69.00   0.50    0.40    --  107.19 -99.00  90.00   54
 30  ω     81.00 107.00   0.50    0.40    --  107.19-125.00  90.00   52
 31  ω     37.00  98.00   0.50    0.40    --  107.19 -99.00 150.00  122
 32  ω     77.00 103.00   0.50    0.40    --  107.19 -99.00  90.00   52
 33  ω     47.00  91.00   0.50    0.40    --  107.19 -99.00 -30.00   88
 34  ω     39.00  89.00   0.50    0.40    --  107.19-125.00 -60.00  100
 35  ω     77.00 102.00   0.50    0.40    --  107.19 -99.00  60.00   50
 36  ω     36.00 104.00   0.50    0.40    --  107.19 -99.00 -60.00  136
 37  ω     79.00 104.00   0.50    0.40    --  107.19 -99.00-120.00   50
 38  ω     74.00  99.00   0.50    0.40    --  107.19 -99.00-150.00   50
 39  ω     37.00  63.00   0.50    0.40    --  107.19 -99.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0240276000
_diffrn_orient_matrix_UB_12      -0.0747904000
_diffrn_orient_matrix_UB_13      -0.1048153000
_diffrn_orient_matrix_UB_21      -0.1080763000
_diffrn_orient_matrix_UB_22      -0.0469119000
_diffrn_orient_matrix_UB_23      0.1293720000
_diffrn_orient_matrix_UB_31      -0.1744418000
_diffrn_orient_matrix_UB_32      0.0187388000
_diffrn_orient_matrix_UB_33      -0.0945833000
_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         0.750
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                1077
_reflns_number_total             1083
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1083
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0208
_refine_ls_restrained_S_all      1.086
_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)+(0.0353P)²+0.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0549
_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. Others
 Fixed Sof: N8(0.5) H8B(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.750000 0.47671(12) 0.4801(3) 0.0301(5) Uani 1 2 d S T P . .
N2 N 0.750000 0.40523(11) 0.5496(2) 0.0257(4) Uani 1 2 d S T P . .
N3 N 0.750000 0.41283(11) 0.7095(2) 0.0226(4) Uani 1 2 d S T P . .
N4 N 0.750000 0.48961(12) 0.7494(3) 0.0287(5) Uani 1 2 d S T P . .
N5 N 0.89719(15) 0.78897(6) 0.69696(16) 0.0165(3) Uani 1 1 d . . . . .
N6 N 0.83768(14) 0.86194(6) 0.66648(16) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.750000 0.52728(12) 0.6048(3) 0.0153(4) Uani 1 2 d S T P . .
C2 C 0.750000 0.61443(12) 0.5826(3) 0.0177(4) Uani 1 2 d S T P . .
H2 H 0.643(3) 0.6299(11) 0.520(3) 0.022(5) Uiso 1 1 d . . . . .
C3 C 0.750000 0.65915(12) 0.7471(3) 0.0169(4) Uani 1 2 d S T P . .
H3 H 0.856(3) 0.6463(12) 0.814(3) 0.034(6) Uiso 1 1 d . . . . .
C4 C 0.750000 0.74582(11) 0.7160(2) 0.0140(4) Uani 1 2 d S T P . .
O1 O 0.750000 0.21005(9) 0.4250(2) 0.0205(4) Uani 1 2 d S T P . .
H1 H 0.750000 0.165(3) 0.357(5) 0.052(11) Uiso 1 2 d S . P . .
N7 N 0.750000 0.27645(10) 0.3187(2) 0.0154(4) Uani 1 2 d S T P . .
H7A H 0.750000 0.315(2) 0.390(4) 0.021(7) Uiso 1 2 d S . P . .
H7B H 0.648(3) 0.2786(11) 0.261(3) 0.019(5) Uiso 1 1 d . . . . .
O2 O 0.750000 0.45002(9) 0.1559(2) 0.0195(3) Uani 1 2 d S T P A 1
H2A H 0.750000 0.464(2) 0.260(5) 0.038(9) Uiso 1 2 d S . P B 1
N8 N 0.9161(3) 0.48210(13) 0.0768(3) 0.0139(5) Uani 0.5 1 d . . P A 1
H8A H 1.038(4) 0.4580(14) 0.106(4) 0.061(8) Uiso 1 1 d . . . C 1
H8B H 0.875(5) 0.486(2) -0.038(5) 0.024(11) Uiso 0.5 1 d . . P D 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0628(15) 0.0122(9) 0.0153(10) 0.0001(7) 0.000 0.000
N2 0.0476(12) 0.0119(9) 0.0176(10) -0.0016(7) 0.000 0.000
N3 0.0391(10) 0.0101(8) 0.0184(10) -0.0001(7) 0.000 0.000
N4 0.0598(13) 0.0095(9) 0.0166(9) -0.0002(7) 0.000 0.000
N5 0.0190(5) 0.0126(6) 0.0179(6) 0.0013(5) 0.0027(5) 0.0011(4)
N6 0.0186(5) 0.0109(5) 0.0151(6) 0.0006(4) 0.0021(5) -0.0001(4)
C1 0.0200(8) 0.0124(9) 0.0134(9) 0.0002(7) 0.000 0.000
C2 0.0303(10) 0.0105(9) 0.0123(10) 0.0008(7) 0.000 0.000
C3 0.0263(10) 0.0122(10) 0.0123(9) -0.0001(8) 0.000 0.000
C4 0.0199(8) 0.0126(9) 0.0094(9) -0.0015(7) 0.000 0.000
O1 0.0327(8) 0.0125(7) 0.0163(7) 0.0017(6) 0.000 0.000
N7 0.0198(9) 0.0109(8) 0.0154(8) -0.0017(7) 0.000 0.000
O2 0.0257(7) 0.0177(7) 0.0150(8) -0.0018(6) 0.000 0.000
N8 0.0133(11) 0.0138(11) 0.0148(12) -0.0007(8) -0.0007(9) -0.0008(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.342(3) . ?
N1 C1 1.323(3) . ?
N2 N3 1.293(3) . ?
N3 N4 1.349(3) . ?
N4 C1 1.329(3) . ?
N5 N6 1.3448(15) . ?
N5 C4 1.3306(16) . ?
N6 N6 1.308(2) 4_655 ?
C1 C2 1.498(3) . ?
C2 H2 0.98(2) 4_655 ?
C2 H2 0.98(2) . ?
C2 C3 1.527(3) . ?
C3 H3 0.98(2) 4_655 ?
C3 H3 0.98(2) . ?
C3 C4 1.501(3) . ?
O1 H1 0.94(4) . ?
O1 N7 1.420(2) . ?
N7 H7A 0.88(3) . ?
N7 H7B 0.89(2) 4_655 ?
N7 H7B 0.89(2) . ?
O2 H2A 0.87(4) . ?
O2 N8 1.496(2) 4_655 ?
O2 N8 1.496(2) . ?
N8 N8 1.393(4) 2_765 ?
N8 H8A 1.03(3) . ?
N8 H8B 0.98(4) . ?

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 106.14(19) . . ?
N3 N2 N1 108.83(19) . . ?
N2 N3 N4 109.5(2) . . ?
C1 N4 N3 105.17(19) . . ?
C4 N5 N6 105.16(11) . . ?
N6 N6 N5 109.26(7) 4_655 . ?
N1 C1 N4 110.34(18) . . ?
N1 C1 C2 123.89(18) . . ?
N4 C1 C2 125.77(18) . . ?
C1 C2 H2 109.2(12) . . ?
C1 C2 H2 109.2(12) . 4_655 ?
C1 C2 C3 113.15(17) . . ?
H2 C2 H2 109(2) . 4_655 ?
C3 C2 H2 108.3(13) . . ?
C3 C2 H2 108.3(13) . 4_655 ?
C2 C3 H3 111.3(14) . 4_655 ?
C2 C3 H3 111.3(14) . . ?
H3 C3 H3 107(3) . 4_655 ?
C4 C3 C2 110.39(17) . . ?
C4 C3 H3 108.2(12) . 4_655 ?
C4 C3 H3 108.2(13) . . ?
N5 C4 N5 111.15(17) 4_655 . ?
N5 C4 C3 124.40(8) 4_655 . ?
N5 C4 C3 124.40(8) . . ?
N7 O1 H1 108(3) . . ?
O1 N7 H7A 102(2) . . ?
O1 N7 H7B 110.3(12) . . ?
O1 N7 H7B 110.3(12) . 4_655 ?
H7A N7 H7B 108.2(15) . 4_655 ?
H7A N7 H7B 108.2(15) . . ?
H7B N7 H7B 117(3) . 4_655 ?
N8 O2 H2A 108.0(12) . . ?
N8 O2 H2A 108.0(11) 4_655 . ?
N8 O2 N8 111.7(2) . 4_655 ?
O2 N8 H8A 119.3(16) . . ?
O2 N8 H8B 100(2) . . ?
N8 N8 O2 154.74(11) 2_765 . ?
N8 N8 H8A 51.6(15) 2_765 . ?
N8 N8 H8B 105(2) 2_765 . ?
H8A N8 H8B 122(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 0.000(1) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?
N2 N1 C1 N4 0.000(1) . . . . ?
N2 N1 C1 C2 180.000(1) . . . . ?
N2 N3 N4 C1 0.000(1) . . . . ?
N3 N4 C1 N1 0.000(1) . . . . ?
N3 N4 C1 C2 180.000(1) . . . . ?
N4 C1 C2 C3 0.000(1) . . . . ?
N6 N5 C4 N5 0.6(2) . . . 4_655 ?
N6 N5 C4 C3 178.00(17) . . . . ?
C1 N1 N2 N3 0.000(1) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C3 C4 N5 -88.55(17) . . . . ?
C2 C3 C4 N5 88.55(17) . . . 4_655 ?
C4 N5 N6 N6 -0.34(13) . . . 4_655 ?
N8 O2 N8 N8 128.8(5) 4_655 . . 2_765 ?

_shelx_res_file                  
;
TITL js122k_a.res in Ima2 js122k.res created by SHELXL-2018/3
    js122k.res
    created by SHELXL-2018/3 at 13:51:25 on 03-Feb-2022
REM Old TITL JS122K in Ima2
REM SHELXT solution in Ima2: R1 0.117, Rweak 0.037, Alpha 0.002
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.066 ( 0.153 ) from 458 Parsons' quotients
REM Formula found by SHELXT: C13 N3 O
CELL 1.54184 7.4569 17.0704 8.044 90 90 90
ZERR 4 0.0001 0.0002 0.0001 0 0 0
LATT -2
SYMM -X,-Y,+Z
SYMM 0.5+X,-Y,+Z
SYMM 0.5-X,+Y,+Z
SFAC C H N O
UNIT 16 48 40 8

L.S. 4 0 0
PLAN  5
SIZE 0.066 0.118 0.167
TEMP -173.15(10)
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\JS122K.hkl">
REM </olex2.extras>

WGHT    0.035300    0.260300
EXTI    0.005735
FVAR       0.79415
N1    3    0.750000    0.476712    0.480141    10.50000    0.06278    0.01220 =
         0.01533    0.00010    0.00000    0.00000
N2    3    0.750000    0.405226    0.549559    10.50000    0.04764    0.01192 =
         0.01760   -0.00157    0.00000    0.00000
N3    3    0.750000    0.412832    0.709477    10.50000    0.03909    0.01014 =
         0.01844   -0.00009    0.00000    0.00000
N4    3    0.750000    0.489608    0.749390    10.50000    0.05979    0.00953 =
         0.01664   -0.00025    0.00000    0.00000
N5    3    0.897188    0.788970    0.696960    11.00000    0.01901    0.01259 =
         0.01791    0.00128    0.00267    0.00115
N6    3    0.837684    0.861938    0.666477    11.00000    0.01858    0.01088 =
         0.01512    0.00055    0.00208   -0.00009
C1    1    0.750000    0.527277    0.604766    10.50000    0.02004    0.01237 =
         0.01341    0.00025    0.00000    0.00000
C2    1    0.750000    0.614427    0.582597    10.50000    0.03034    0.01054 =
         0.01228    0.00080    0.00000    0.00000
H2    2    0.643127    0.629853    0.519547    11.00000    0.02152
C3    1    0.750000    0.659152    0.747062    10.50000    0.02633    0.01220 =
         0.01227   -0.00011    0.00000    0.00000
H3    2    0.856383    0.646275    0.814258    11.00000    0.03361
C4    1    0.750000    0.745824    0.715951    10.50000    0.01994    0.01262 =
         0.00937   -0.00155    0.00000    0.00000
O1    4    0.750000    0.210049    0.425034    10.50000    0.03272    0.01255 =
         0.01629    0.00173    0.00000    0.00000
H1    2    0.750000    0.165284    0.357479    10.50000    0.05188
N7    3    0.750000    0.276448    0.318683    10.50000    0.01979    0.01087 =
         0.01542   -0.00174    0.00000    0.00000
H7A   2    0.750000    0.315189    0.390395    10.50000    0.02141
H7B   2    0.648168    0.278569    0.260753    11.00000    0.01892
PART 1
O2    4    0.750000    0.450018    0.155863    10.50000    0.02571    0.01771 =
         0.01497   -0.00184    0.00000    0.00000
H2A   2    0.750000    0.463981    0.259645    10.50000    0.03836
N8    3    0.916091    0.482097    0.076761    10.50000    0.01328    0.01375 =
         0.01479   -0.00074   -0.00073   -0.00077
H8A   2    1.038456    0.457951    0.106303    11.00000    0.06098
H8B   2    0.874907    0.485817   -0.038124    10.50000    0.02407
HKLF 4




REM  js122k_a.res in Ima2 js122k.res created by SHELXL-2018/3
REM wR2 = 0.0549, GooF = S = 1.087, Restrained GooF = 1.086 for all data
REM R1 = 0.0208 for 1077 Fo > 4sig(Fo) and 0.0209 for all 1083 data
REM 124 parameters refined using 1 restraints

END

WGHT      0.0353      0.2604

REM Highest difference peak  0.227,  deepest hole -0.145,  1-sigma level  0.029
Q1    1   0.7500  0.6387  0.6609  10.50000  0.05    0.23
Q2    1   0.7500  0.5740  0.6093  10.50000  0.05    0.17
Q3    1   0.7500  0.7031  0.7096  10.50000  0.05    0.16
Q4    1   0.8843  0.9001  0.6579  11.00000  0.05    0.15
Q5    1   0.7500  0.4820  0.4101  10.50000  0.05    0.14
;
_shelx_res_checksum              32015
_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 JS293
_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 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.811
_vrf_PLAT089_js122k              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........ 4.99 Note
RESPONSE: We used the data ato find and refine the hydrogen atoms isotropically
 to inprove hydrogen bonding scheme, this resulted in the value to be lower 
than is commonly accepted.
;
