# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_js222b
_database_code_depnum_ccdc_archive 'CCDC 2296314'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2022-02-21
_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         'C6 H9 N7 O8'
_chemical_formula_sum            'C6 H9 N7 O8'
_chemical_formula_weight         307.20
_chemical_melting_point          401
_chemical_oxdiff_formula         C6H9N7O8
_chemical_oxdiff_usercomment     'Colorless Blocks'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.2321(2)
_cell_length_b                   10.9604(3)
_cell_length_c                   35.1593(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2401.60(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4960
_cell_measurement_theta_min      5.0170
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    1.395
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.872
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0186
0 0 1 0.0264
0 1 0 0.0619
0 -2 1 0.0587
-1 0 -1 0.0096
1 0 1 0.0096
-1 3 19 0.0286

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.019
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0009 -0.0021 -0.9998 -0.0102 -0.0392 0.0168
0.0009 0.0021 0.9998 0.0102 0.0392 -0.0168
-0.0004 1.0004 -0.0111 0.0036 0.0550 0.1293
0.0017 -1.9986 1.0220 0.0031 -0.0709 -0.2755
-1.0025 -0.0049 -0.9918 0.2302 -0.0957 0.0340
1.0025 0.0049 0.9918 -0.2302 0.0957 -0.0340
-1.2913 3.3873 18.7032 0.5173 0.8441 0.1410

_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  0.0453
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            8297
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.295
_diffrn_reflns_theta_min         2.513
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -40.00   0.50    1.44    --  -47.62 -30.00-173.00  156
  2  ω    -87.00 -28.00   0.50    5.76    --  -91.75 145.00  12.00  118
  3  ω   -159.00 -84.00   0.50    5.76    --  -91.75 -30.00-173.00  150
  4  ω    138.00 165.00   0.50    5.76    --  107.19  92.00 131.00   54
  5  ω    -79.00 -50.00   0.50    1.44    --  -47.62 125.00 120.00   58
  6  ω    -24.00   2.00   0.50    1.44    --  -47.62  19.00 150.00   52
  7  ω    -67.00 -40.00   0.50    1.44    --  -47.62 125.00 -90.00   54
  8  ω   -162.00-133.00   0.50    5.76    --  -91.75 -77.00 -90.00   58
  9  ω   -153.00-127.00   0.50    5.76    --  -91.75 -57.00 120.00   52
 10  ω   -153.00-126.00   0.50    5.76    --  -91.75 -77.00 -30.00   54
 11  ω   -161.00-135.00   0.50    5.76    --  -91.75 -77.00 120.00   52
 12  ω     80.00 106.00   0.50    5.76    --  107.19-125.00  90.00   52
 13  ω     40.00  66.00   0.50    5.76    --  107.19-125.00  90.00   52
 14  ω     39.00  64.00   0.50    5.76    --  107.19 -57.00  90.00   50
 15  ω     35.00  60.00   0.50    5.76    --  107.19 -57.00   0.00   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      -0.2399408000
_diffrn_orient_matrix_UB_12      0.0035684000
_diffrn_orient_matrix_UB_13      0.0104440000
_diffrn_orient_matrix_UB_21      0.0565783000
_diffrn_orient_matrix_UB_22      0.0554811000
_diffrn_orient_matrix_UB_23      0.0389910000
_diffrn_orient_matrix_UB_31      -0.0176628000
_diffrn_orient_matrix_UB_32      0.1291003000
_diffrn_orient_matrix_UB_33      -0.0170608000
_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                2042
_reflns_number_total             2332
_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    
;
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         0.406
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.055
_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)+(0.0539P)²+1.7068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1168
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
;
_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 0.3316(2) 0.60061(12) 0.37224(4) 0.0291(3) Uani 1 1 d . . . . .
O2 O 0.5434(2) 0.74443(12) 0.35144(4) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.4768(2) 0.16952(12) 0.30129(4) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.7623(3) 0.10654(15) 0.26878(5) 0.0434(4) Uani 1 1 d . . . . .
O5 O 0.5407(3) -0.02284(13) 0.29357(5) 0.0354(4) Uani 1 1 d . . . . .
O6 O 1.0600(2) 0.30119(13) 0.43344(4) 0.0301(3) Uani 1 1 d . . . . .
O7 O 1.1352(4) 0.32675(17) 0.49497(5) 0.0550(5) Uani 1 1 d . . . . .
O8 O 1.1245(3) 0.14628(15) 0.46986(5) 0.0438(4) Uani 1 1 d . . . . .
N1 N 0.4548(3) 0.28125(15) 0.38129(5) 0.0241(4) Uani 1 1 d . . . . .
H1 H 0.370(5) 0.217(3) 0.3768(7) 0.048(8) Uiso 1 1 d . . . . .
N2 N 0.5520(3) 0.30103(14) 0.41580(5) 0.0244(4) Uani 1 1 d . . . . .
N3 N 0.6187(2) 0.44907(13) 0.37516(4) 0.0211(3) Uani 1 1 d . . . . .
N4 N 0.6849(3) 0.56397(14) 0.36131(5) 0.0247(4) Uani 1 1 d . . . . .
N5 N 0.5147(3) 0.63814(14) 0.36206(5) 0.0237(4) Uani 1 1 d . . . . .
N6 N 0.6045(3) 0.07799(15) 0.28653(5) 0.0301(4) Uani 1 1 d . . . . .
N7 N 1.1111(3) 0.25585(18) 0.46941(5) 0.0355(4) Uani 1 1 d . . . . .
C1 C 0.4934(3) 0.36842(16) 0.35682(6) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.6512(3) 0.40502(16) 0.41137(5) 0.0222(4) Uani 1 1 d . . . . .
C3 C 0.4198(4) 0.37605(17) 0.31689(6) 0.0281(4) Uani 1 1 d . . . . .
H3A H 0.435464 0.461007 0.307743 0.034 Uiso 1 1 calc R U . . .
H3B H 0.265916 0.354101 0.315573 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5477(4) 0.29114(17) 0.29125(6) 0.0285(4) Uani 1 1 d . . . . .
H4A H 0.517745 0.308501 0.264129 0.034 Uiso 1 1 calc R U . . .
H4B H 0.703600 0.300424 0.295847 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7946(3) 0.46491(18) 0.43965(5) 0.0268(4) Uani 1 1 d . . . . .
H5A H 0.755139 0.438052 0.465612 0.032 Uiso 1 1 calc R U . . .
H5B H 0.776267 0.554521 0.438284 0.032 Uiso 1 1 calc R U . . .
C6 C 1.0284(3) 0.43203(19) 0.43172(6) 0.0308(5) Uani 1 1 d . . . . .
H6A H 1.069492 0.462194 0.406192 0.037 Uiso 1 1 calc R U . . .
H6B H 1.121978 0.472311 0.450698 0.037 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 N5 1.265(2) . ?
O2 N5 1.236(2) . ?
O3 N6 1.382(2) . ?
O3 C4 1.448(2) . ?
O4 N6 1.206(2) . ?
O5 N6 1.200(2) . ?
O6 N7 1.396(2) . ?
O6 C6 1.449(3) . ?
O7 N7 1.197(2) . ?
O8 N7 1.204(2) . ?
N1 H1 0.90(3) . ?
N1 N2 1.373(2) . ?
N1 C1 1.308(3) . ?
N2 C2 1.306(2) . ?
N3 N4 1.412(2) . ?
N3 C1 1.344(2) . ?
N3 C2 1.377(2) . ?
N4 N5 1.336(2) . ?
C1 C3 1.479(3) . ?
C2 C5 1.490(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.521(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.527(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 O3 C4 113.64(15) . . ?
N7 O6 C6 114.91(15) . . ?
N2 N1 H1 122.6(17) . . ?
C1 N1 H1 124.7(17) . . ?
C1 N1 N2 112.62(16) . . ?
C2 N2 N1 103.95(15) . . ?
C1 N3 N4 126.22(16) . . ?
C1 N3 C2 107.35(15) . . ?
C2 N3 N4 126.09(15) . . ?
N5 N4 N3 107.71(14) . . ?
O1 N5 N4 121.58(15) . . ?
O2 N5 O1 121.50(15) . . ?
O2 N5 N4 116.90(15) . . ?
O4 N6 O3 118.39(16) . . ?
O5 N6 O3 113.60(17) . . ?
O5 N6 O4 128.01(18) . . ?
O7 N7 O6 118.52(18) . . ?
O7 N7 O8 129.0(2) . . ?
O8 N7 O6 112.50(17) . . ?
N1 C1 N3 105.77(17) . . ?
N1 C1 C3 127.49(18) . . ?
N3 C1 C3 126.73(18) . . ?
N2 C2 N3 110.30(16) . . ?
N2 C2 C5 126.08(17) . . ?
N3 C2 C5 123.44(16) . . ?
C1 C3 H3A 109.3 . . ?
C1 C3 H3B 109.3 . . ?
C1 C3 C4 111.44(16) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
O3 C4 C3 104.98(16) . . ?
O3 C4 H4A 110.7 . . ?
O3 C4 H4B 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C2 C5 H5A 109.6 . . ?
C2 C5 H5B 109.6 . . ?
C2 C5 C6 110.28(16) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
O6 C6 C5 110.82(16) . . ?
O6 C6 H6A 109.5 . . ?
O6 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?

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 O1 0.90(3) 1.79(3) 2.685(2) 171(3) 8_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 N3 -0.4(2) . . . . ?
N1 N2 C2 C5 -175.67(18) . . . . ?
N1 C1 C3 C4 -75.7(3) . . . . ?
N2 N1 C1 N3 -0.2(2) . . . . ?
N2 N1 C1 C3 178.39(18) . . . . ?
N2 C2 C5 C6 94.8(2) . . . . ?
N3 N4 N5 O1 -3.0(2) . . . . ?
N3 N4 N5 O2 178.79(15) . . . . ?
N3 C1 C3 C4 102.7(2) . . . . ?
N3 C2 C5 C6 -79.9(2) . . . . ?
N4 N3 C1 N1 -173.61(16) . . . . ?
N4 N3 C1 C3 7.8(3) . . . . ?
N4 N3 C2 N2 173.86(16) . . . . ?
N4 N3 C2 C5 -10.7(3) . . . . ?
N6 O3 C4 C3 -167.77(15) . . . . ?
N7 O6 C6 C5 -89.1(2) . . . . ?
C1 N1 N2 C2 0.4(2) . . . . ?
C1 N3 N4 N5 72.5(2) . . . . ?
C1 N3 C2 N2 0.3(2) . . . . ?
C1 N3 C2 C5 175.71(17) . . . . ?
C1 C3 C4 O3 71.6(2) . . . . ?
C2 N3 N4 N5 -99.9(2) . . . . ?
C2 N3 C1 N1 0.0(2) . . . . ?
C2 N3 C1 C3 -178.65(18) . . . . ?
C2 C5 C6 O6 -59.1(2) . . . . ?
C4 O3 N6 O4 3.1(2) . . . . ?
C4 O3 N6 O5 -177.13(16) . . . . ?
C6 O6 N7 O7 -3.7(3) . . . . ?
C6 O6 N7 O8 176.29(17) . . . . ?

_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 sohan-143
_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 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.828
####################################################################### 
# 
# 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_js10123d
_database_code_depnum_ccdc_archive 'CCDC 2303917'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2023-10-26 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-10-19
_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         '2(C2 H3 N5 O2), 2(H2 O)'
_chemical_formula_sum            'C4 H10 N10 O6'
_chemical_formula_weight         294.22
_chemical_absolute_configuration .
_chemical_melting_point          478
_chemical_oxdiff_formula         C2H9N7O4
_chemical_oxdiff_usercomment     JMS-SOHAN-800-HA
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.16088(12)
_cell_length_b                   8.67413(16)
_cell_length_c                   6.54739(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.652(2)
_cell_angle_gamma                90
_cell_volume                     280.810(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2140
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.5270
_cell_measurement_theta_min      7.0460
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 0 0.0355
2 0 -4 0.0201
-2 0 4 0.0132
3 -3 -2 0.0461
-3 1 0 0.0431
3 -1 0 0.0728
-1 1 -3 0.0393
3 3 -1 0.0475
2 4 0 0.0446
0 3 3 0.0366

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.035
_exptl_crystal_size_rad          0.040
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
1.2788 -5.1907 -0.1938 0.9186 0.1706 0.3565
2.0823 0.1057 -3.9453 0.4655 0.2514 -0.8486
-2.0487 -0.1974 3.9628 -0.4501 -0.2431 0.8592
2.5634 -3.4392 -1.7584 0.8731 0.4737 -0.1152
-3.0836 1.3171 -0.1525 -0.4274 -0.8961 -0.1193
3.0910 -1.3037 0.1303 0.4277 0.8967 0.1136
-1.0881 0.9340 -3.3957 0.0498 -0.6216 -0.7818
2.9349 2.6526 -1.4851 -0.0656 0.8435 -0.5332
1.9970 4.3813 0.0820 -0.5336 0.7773 -0.3332
0.1092 3.3225 3.2454 -0.7724 0.4729 0.4240

_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2882
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.067
_diffrn_reflns_theta_min         7.059
_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 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -21.00   0.50    0.06    --  -91.75  61.00  60.00   82
  2  ω    -48.00 -20.00   0.50    0.06    --  -91.75  45.00   0.00   56
  3  ω    -14.00  22.00   0.50    0.05    --  -47.12  87.00-135.00   72
  4  ω    -72.00 -33.00   0.50    0.05    --  -47.12  87.00-135.00   78
  5  ω    -42.00 -17.00   0.50    0.06    --  -91.75  15.00-180.00   50
  6  ω    -77.00 -51.00   0.50    0.06    --  -91.75  87.00-135.00   52
  7  ω     21.00  48.00   0.50    0.05    --   47.12 -87.00 107.00   54
  8  ω    -17.00  12.00   0.50    0.05    --   47.12 -87.00 107.00   58
  9  ω     48.00  92.00   0.50    0.06    --  113.25 -77.00 150.00   88
 10  ω     42.00  67.00   0.50    0.06    --  113.25 -61.00 150.00   50
 11  ω     72.00 104.00   0.50    0.06    --  113.25 -87.00 107.00   64
 12  ω     44.00  69.00   0.50    0.06    --  113.25 -61.00  90.00   50
 13  ω     49.00  91.00   0.50    0.06    --  113.25 -77.00   0.00   84
 14  ω     44.00  69.00   0.50    0.06    --  113.25 -61.00  30.00   50
 15  ω     42.00  67.00   0.50    0.06    --  113.25 -61.00 120.00   50
 16  ω     42.00  67.00   0.50    0.06    --  113.25 -61.00   0.00   50
 17  ω     42.00  89.00   0.50    0.06    --  113.25 -77.00 -60.00   94
 18  ω    -24.00  28.00   0.50    0.05    --   47.12 -19.00-180.00  104
 19  ω     42.00  67.00   0.50    0.06    --  113.25 -61.00-150.00   50
 20  ω     44.00  69.00   0.50    0.06    --  113.25 -61.00-180.00   50
 21  ω    106.00 141.00   0.50    0.06    --  113.25  87.00-135.00   70
 22  ω    150.00 178.00   0.50    0.06    --  113.25  87.00-135.00   56
 23  ω    110.00 171.00   0.50    0.06    --  113.25  61.00-180.00  122
 24  ω    128.00 159.00   0.50    0.06    --  113.25  45.00 150.00   62
 25  ω    -79.00 -38.00   0.50    0.05    --  -47.12 -37.00 120.00   82
 26  ω   -118.00 -89.00   0.50    0.05    --  -47.12 -37.00 120.00   58
 27  ω   -142.00-116.00   0.50    0.06    --  -91.75 -87.00 107.00   52
 28  ω    -51.00 -25.00   0.50    0.06    --  -91.75  87.00-135.00   52
 29  ω   -101.00 -43.00   0.50    0.05    --  -47.12 -37.00  60.00  116
 30  ω    -22.00  38.00   0.50    0.05    --   47.12 -19.00  90.00  120
 31  ω   -136.00 -82.00   0.50    0.06    --  -91.75 -30.00   0.00  108
 32  ω    151.00 176.00   0.50    0.06    --  113.25  30.00   0.00   50
 33  ω    134.00 176.00   0.50    0.06    --  113.25  45.00 -60.00   84
 34  ω     64.00 106.00   0.50    0.06    --  113.25-125.00 120.00   84
 35  ω    103.00 128.00   0.50    0.06    --  113.25  45.00 -60.00   50
 36  ω    127.00 175.00   0.50    0.06    --  113.25  61.00 -90.00   96
 37  ω    119.00 176.00   0.50    0.06    --  113.25  61.00 -30.00  114
 38  ω    107.00 136.00   0.50    0.06    --  113.25  61.00 150.00   58
 39  ω     55.00 107.00   0.50    0.06    --  113.25-125.00 -60.00  104
 40  ω    101.00 127.00   0.50    0.06    --  113.25  30.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0764190000
_diffrn_orient_matrix_UB_12      -0.1550865000
_diffrn_orient_matrix_UB_13      -0.0818034000
_diffrn_orient_matrix_UB_21      0.3020399000
_diffrn_orient_matrix_UB_22      0.0379397000
_diffrn_orient_matrix_UB_23      0.0967009000
_diffrn_orient_matrix_UB_31      -0.0049155000
_diffrn_orient_matrix_UB_32      -0.0777515000
_diffrn_orient_matrix_UB_33      0.2104139000
_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         0.824
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                1153
_reflns_number_total             1171
_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.91a 64-bit (release 29-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (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         0.191
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.17(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1171
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.063
_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)+(0.0442P)²+0.0492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0754
_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
O1 O 0.6466(3) 0.82067(18) 0.8668(3) 0.0187(4) Uani 1 1 d . . . . .
O2 O 0.3232(3) 0.6627(2) 0.7072(3) 0.0194(4) Uani 1 1 d . . . . .
O3 O -0.0582(4) 0.4526(2) 0.4188(3) 0.0237(4) Uani 1 1 d . . . . .
N5 N 0.5636(4) 0.6854(2) 0.8100(3) 0.0156(4) Uani 1 1 d . . . . .
N4 N 0.7457(4) 0.5746(2) 0.8695(3) 0.0158(4) Uani 1 1 d . . . . .
N3 N 0.8201(4) 0.3086(3) 0.8724(3) 0.0163(4) Uani 1 1 d . . . . .
N1 N 0.4216(4) 0.3717(2) 0.6838(3) 0.0157(4) Uani 1 1 d . . . . .
N2 N 0.4356(5) 0.2139(2) 0.6716(3) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.6532(4) 0.4310(3) 0.8064(3) 0.0152(5) Uani 1 1 d . . . . .
C2 C 0.6805(5) 0.1805(3) 0.7878(4) 0.0174(5) Uani 1 1 d . . . . .
H2 H 0.751694 0.078847 0.810060 0.021 Uiso 1 1 calc R U . . .
H3A H -0.150(8) 0.531(5) 0.400(6) 0.023(8) Uiso 1 1 d . . . . .
H3B H -0.159(8) 0.376(5) 0.372(6) 0.029(9) Uiso 1 1 d . . . . .
H3 H 0.985(8) 0.318(6) 0.956(7) 0.044(11) Uiso 1 1 d . . . . .
H1 H 0.262(8) 0.424(5) 0.605(6) 0.035(10) 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 N5 1.268(3) . ?
O2 N5 1.246(3) . ?
O3 H3A 0.82(4) . ?
O3 H3B 0.85(4) . ?
N5 N4 1.322(3) . ?
N4 C1 1.356(3) . ?
N3 C1 1.357(3) . ?
N3 C2 1.354(4) . ?
N3 H3 0.88(4) . ?
N1 N2 1.374(3) . ?
N1 C1 1.337(3) . ?
N1 H1 0.95(4) . ?
N2 C2 1.307(3) . ?
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
H3A O3 H3B 109(4) . . ?
O1 N5 N4 115.74(19) . . ?
O2 N5 O1 120.29(19) . . ?
O2 N5 N4 124.0(2) . . ?
N5 N4 C1 114.8(2) . . ?
C1 N3 H3 123(3) . . ?
C2 N3 C1 107.29(19) . . ?
C2 N3 H3 130(3) . . ?
N2 N1 H1 120(2) . . ?
C1 N1 N2 111.4(2) . . ?
C1 N1 H1 129(2) . . ?
C2 N2 N1 104.2(2) . . ?
N4 C1 N3 119.1(2) . . ?
N1 C1 N4 135.4(2) . . ?
N1 C1 N3 105.5(2) . . ?
N3 C2 H2 124.2 . . ?
N2 C2 N3 111.6(2) . . ?
N2 C2 H2 124.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3B O2 0.85(4) 2.04(4) 2.868(3) 167(4) 2_546 yes
N3 H3 O1 0.88(4) 1.92(4) 2.794(3) 175(4) 2_747 yes
N1 H1 O3 0.95(4) 1.77(4) 2.678(3) 159(4) . 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 N5 N4 C1 -179.73(19) . . . . ?
O2 N5 N4 C1 1.3(3) . . . . ?
N5 N4 C1 N3 -175.5(2) . . . . ?
N5 N4 C1 N1 5.3(4) . . . . ?
N1 N2 C2 N3 0.2(3) . . . . ?
N2 N1 C1 N4 179.9(2) . . . . ?
N2 N1 C1 N3 0.6(3) . . . . ?
C1 N3 C2 N2 0.2(3) . . . . ?
C1 N1 N2 C2 -0.5(3) . . . . ?
C2 N3 C1 N4 -179.9(2) . . . . ?
C2 N3 C1 N1 -0.5(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'JMS-SOHAN-800 HA'
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.858
####################################################################### 
# 
# 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_js923b
_database_code_depnum_ccdc_archive 'CCDC 2296315'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H2 K N5 O2'
_chemical_formula_sum            'C2 H2 K N5 O2'
_chemical_formula_weight         167.19
_chemical_absolute_configuration ad
_chemical_melting_point          533
_chemical_oxdiff_formula         C4H4K3N10O4
_chemical_oxdiff_usercomment     SOHAN-800-K
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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.07223(5)
_cell_length_b                   10.00743(14)
_cell_length_c                   6.99455(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.2041(13)
_cell_angle_gamma                90
_cell_volume                     276.331(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4771
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.3940
_cell_measurement_theta_min      6.5190
_shelx_estimated_absorpt_T_max   0.526
_shelx_estimated_absorpt_T_min   0.354
_exptl_absorpt_coefficient_mu    8.001
_exptl_absorpt_correction_T_max  0.588
_exptl_absorpt_correction_T_min  0.395
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.009
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             168
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -3 -1 0.0470
-2 -3 2 0.0352
-1 6 -1 0.0649
2 4 -2 0.0829
0 3 4 0.0410
0 -6 0 0.0823
0 -2 -4 0.0535
0 4 -3 0.0588
0 -3 4 0.0673
-2 4 3 0.0618
-1 -2 4 0.0507
2 -2 0 0.0430
-3 -1 1 0.0390
2 4 -1 0.0742
2 1 1 0.0354

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.092
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
2.3544 -2.8701 -0.6285 -0.7351 0.3481 0.5777
-2.3115 -2.7888 1.9383 0.8496 -0.4031 0.3354
-1.0680 5.6730 -0.7450 0.2337 -0.1101 -0.9657
1.9723 3.9434 -2.0224 -0.7607 0.3610 -0.5379
0.1678 2.5037 3.9780 -0.4261 -0.9020 -0.0628
0.3362 -6.4323 -0.0137 0.1223 0.2595 0.9563
-0.2403 -1.5258 -4.1563 0.4276 0.8985 -0.0973
-0.4518 4.3274 -2.9997 0.2041 0.4321 -0.8777
0.4284 -2.8488 3.7044 -0.2995 -0.6332 0.7126
-1.5995 3.7768 3.0597 0.2527 -0.8451 -0.4684
-1.2524 -1.7447 4.2193 0.2573 -0.8599 0.4411
2.4877 -1.6816 -0.1230 -0.8651 0.2062 0.4541
-2.5795 -1.2887 0.7642 0.9714 -0.2310 0.0117
1.9060 4.4354 -1.2897 -0.8037 0.1891 -0.5625
2.2454 1.2993 1.1784 -0.9758 -0.1838 0.0955

_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5570
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.665
_diffrn_reflns_theta_min         6.528
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_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 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     66.00  92.00   0.50    0.05    --  113.25 -94.00-120.00   52
  2  ω     44.00 108.00   0.50    0.05    --  113.25-125.00  90.00  128
  3  ω     64.00 108.00   0.50    0.05    --  113.25-125.00 120.00   88
  4  ω     42.00 104.00   0.50    0.05    --  113.25 -94.00   0.00  124
  5  ω     42.00  94.00   0.50    0.05    --  113.25 -77.00   0.00  104
  6  ω     50.00  94.00   0.50    0.05    --  113.25 -77.00  90.00   88
  7  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00 -90.00   54
  8  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00-150.00   54
  9  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00-180.00   54
 10  ω     42.00  94.00   0.50    0.05    --  113.25 -77.00-120.00  104
 11  ω     43.00  68.00   0.50    0.05    --  113.25 -61.00 -60.00   50
 12  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00 150.00   54
 13  ω    -27.00  40.00   0.50    0.05    --   47.11 -27.00 142.00  134
 14  ω    110.00 178.00   0.50    0.05    --  113.25  77.00  30.00  136
 15  ω    101.00 178.00   0.50    0.05    --  113.25  45.00   0.00  154
 16  ω    126.00 170.00   0.50    0.05    --  113.25  77.00 -60.00   88
 17  ω    117.00 156.00   0.50    0.05    --  113.25  61.00   0.00   78
 18  ω    106.00 178.00   0.50    0.05    --  113.25  61.00  60.00  144
 19  ω    110.00 178.00   0.50    0.05    --  113.25  77.00 120.00  136
 20  ω    108.00 133.00   0.50    0.05    --  113.25  45.00 120.00   50
 21  ω    101.00 178.00   0.50    0.05    --  113.25  45.00  90.00  154
 22  ω    101.00 178.00   0.50    0.05    --  113.25  45.00  60.00  154
 23  ω    101.00 178.00   0.50    0.05    --  113.25  27.00 -54.00  154
 24  ω    101.00 178.00   0.50    0.05    --  113.25  45.00-180.00  154
 25  ω     35.00 121.00   0.50    0.05    --   47.11  27.00 -54.00  172
 26  ω     35.00 120.00   0.50    0.05    --   47.11  37.00   0.00  170
 27  ω     35.00 119.00   0.50    0.05    --   47.11  46.00  75.38  168
 28  ω     35.00 120.00   0.50    0.05    --   47.11  37.00 150.00  170
 29  ω    -41.00  28.00   0.50    0.05    --  -47.11  27.00 -54.00  138
 30  ω    -47.00  26.00   0.50    0.05    --  -47.11  37.00   0.00  146
 31  ω    -53.00 -20.00   0.50    0.05    --  -91.75  45.00 -60.00   66
 32  ω   -119.00 -34.00   0.50    0.05    --  -47.11 -45.00 -23.31  170
 33  ω   -120.00 -35.00   0.50    0.05    --  -47.11 -37.00  30.00  170
 34  ω   -121.00 -35.00   0.50    0.05    --  -47.11 -27.00 142.00  172
 35  ω   -163.00 -88.00   0.50    0.05    --  -91.75 -48.00  60.46  150
 36  ω   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00  90.00  168
 37  ω   -163.00 -82.00   0.50    0.05    --  -91.75 -47.00 -18.07  162
 38  ω   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00 -30.00  168
 39  ω   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00   0.00  168
 40  ω   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00  30.00  168
 41  ω   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00  60.00  168
 42  ω   -166.00 -79.00   0.50    0.05    --  -91.75 -27.00 142.00  174
 43  ω   -166.00 -79.00   0.50    0.05    --  -91.75 -30.00  60.00  174
 44  ω   -161.00 -94.00   0.50    0.05    --  -91.75-125.00 -60.00  134
;
_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      -0.3771276000
_diffrn_orient_matrix_UB_12      -0.0385878000
_diffrn_orient_matrix_UB_13      -0.0669066000
_diffrn_orient_matrix_UB_21      0.0474629000
_diffrn_orient_matrix_UB_22      -0.0374214000
_diffrn_orient_matrix_UB_23      -0.2051914000
_diffrn_orient_matrix_UB_31      0.0886027000
_diffrn_orient_matrix_UB_32      -0.1441950000
_diffrn_orient_matrix_UB_33      0.0712213000
_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         0.769
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                1117
_reflns_number_total             1123
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (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         0.249
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(9)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1123
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.127
_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)+(0.0493P)²+0.0668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0708
_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
K1 K 0.94866(13) 0.67954(6) -0.14381(8) 0.0165(2) Uani 1 1 d . . . . .
O1 O 0.8629(5) 0.4390(2) 0.0182(3) 0.0185(5) Uani 1 1 d . . . . .
O2 O 0.6174(6) 0.5952(2) 0.1534(3) 0.0186(5) Uani 1 1 d . . . . .
N1 N 0.4071(7) 0.5360(3) 0.4690(4) 0.0152(5) Uani 1 1 d . . . . .
H1 H 0.443(12) 0.608(6) 0.431(8) 0.029(13) Uiso 1 1 d . . . . .
N2 N 0.2756(7) 0.5195(3) 0.6306(4) 0.0173(6) Uani 1 1 d . . . . .
N3 N 0.4122(7) 0.3190(3) 0.5224(4) 0.0167(6) Uani 1 1 d . . . . .
N4 N 0.6362(7) 0.3796(3) 0.2570(4) 0.0156(5) Uani 1 1 d . . . . .
N5 N 0.7025(6) 0.4751(3) 0.1436(4) 0.0144(5) Uani 1 1 d . . . . .
C1 C 0.4879(7) 0.4158(3) 0.4075(4) 0.0149(6) Uani 1 1 d . . . . .
C2 C 0.2847(8) 0.3887(3) 0.6534(4) 0.0169(6) Uani 1 1 d . . . . .
H2 H 0.206776 0.346104 0.755419 0.020 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
K1 O1 2.720(2) . ?
K1 O1 2.788(2) 2_755 ?
K1 O2 3.110(3) 1_655 ?
K1 O2 2.869(2) . ?
K1 N2 3.232(3) 1_554 ?
K1 N2 2.803(3) 1_654 ?
K1 N3 3.035(3) 2_655 ?
K1 N4 2.855(3) 2_755 ?
K1 N4 3.063(3) 2_655 ?
K1 N5 3.197(3) . ?
K1 N5 3.281(3) 2_755 ?
K1 C1 3.247(3) 2_655 ?
O1 N5 1.268(3) . ?
O2 N5 1.258(4) . ?
N1 H1 0.79(6) . ?
N1 N2 1.374(3) . ?
N1 C1 1.345(4) . ?
N2 C2 1.318(5) . ?
N3 C1 1.342(4) . ?
N3 C2 1.353(4) . ?
N4 N5 1.312(4) . ?
N4 C1 1.384(4) . ?
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
O1 K1 O1 138.31(2) . 2_755 ?
O1 K1 O2 100.81(7) 2_755 . ?
O1 K1 O2 46.08(7) . . ?
O1 K1 O2 85.06(7) 2_755 1_655 ?
O1 K1 O2 70.25(6) . 1_655 ?
O1 K1 N2 125.28(8) 2_755 1_654 ?
O1 K1 N2 65.46(7) . 1_554 ?
O1 K1 N2 138.62(7) 2_755 1_554 ?
O1 K1 N2 81.73(8) . 1_654 ?
O1 K1 N3 133.36(7) . 2_655 ?
O1 K1 N3 83.31(7) 2_755 2_655 ?
O1 K1 N4 45.44(7) 2_755 2_755 ?
O1 K1 N4 121.00(7) . 2_655 ?
O1 K1 N4 151.84(7) . 2_755 ?
O1 K1 N4 67.00(7) 2_755 2_655 ?
O1 K1 N5 22.26(6) 2_755 2_755 ?
O1 K1 N5 120.16(7) 2_755 . ?
O1 K1 N5 153.85(6) . 2_755 ?
O1 K1 N5 22.97(7) . . ?
O1 K1 C1 140.61(7) . 2_655 ?
O1 K1 C1 64.58(7) 2_755 2_655 ?
O2 K1 O2 85.76(6) . 1_655 ?
O2 K1 N2 133.67(7) 1_655 1_554 ?
O2 K1 N2 73.43(7) . 1_554 ?
O2 K1 N3 123.68(7) . 2_655 ?
O2 K1 N4 84.58(7) . 2_655 ?
O2 K1 N5 76.36(6) 1_655 . ?
O2 K1 N5 123.05(7) . 2_755 ?
O2 K1 N5 86.35(6) 1_655 2_755 ?
O2 K1 N5 23.12(7) . . ?
O2 K1 C1 109.67(7) . 2_655 ?
O2 K1 C1 147.66(7) 1_655 2_655 ?
N2 K1 O2 127.77(8) 1_654 . ?
N2 K1 O2 76.25(7) 1_654 1_655 ?
N2 K1 N2 84.55(7) 1_654 1_554 ?
N2 K1 N3 88.10(7) 1_654 2_655 ?
N2 K1 N4 81.32(8) 1_654 2_755 ?
N2 K1 N4 132.41(8) 1_654 2_655 ?
N2 K1 N5 104.48(8) 1_654 2_755 ?
N2 K1 N5 104.70(8) 1_654 . ?
N2 K1 N5 139.66(7) 1_554 2_755 ?
N2 K1 C1 111.45(8) 1_654 2_655 ?
N2 K1 C1 78.63(7) 1_554 2_655 ?
N3 K1 O2 149.90(7) 2_655 1_655 ?
N3 K1 N2 68.34(7) 2_655 1_554 ?
N3 K1 N4 45.13(7) 2_655 2_655 ?
N3 K1 N5 72.70(7) 2_655 2_755 ?
N3 K1 N5 133.13(7) 2_655 . ?
N3 K1 C1 24.37(7) 2_655 2_655 ?
N4 K1 O2 148.00(7) 2_655 1_655 ?
N4 K1 O2 145.40(7) 2_755 . ?
N4 K1 O2 83.96(7) 2_755 1_655 ?
N4 K1 N2 134.51(7) 2_755 1_554 ?
N4 K1 N2 71.65(8) 2_655 1_554 ?
N4 K1 N3 68.18(7) 2_755 2_655 ?
N4 K1 N4 86.89(8) 2_755 2_655 ?
N4 K1 N5 157.16(7) 2_755 . ?
N4 K1 N5 23.40(7) 2_755 2_755 ?
N4 K1 N5 73.74(7) 2_655 2_755 ?
N4 K1 N5 103.71(7) 2_655 . ?
N4 K1 C1 67.09(8) 2_755 2_655 ?
N4 K1 C1 25.12(7) 2_655 2_655 ?
N5 K1 N2 68.33(7) . 1_554 ?
N5 K1 N5 141.18(4) . 2_755 ?
N5 K1 C1 127.64(7) . 2_655 ?
C1 K1 N5 61.35(7) 2_655 2_755 ?
K1 O1 K1 154.46(8) . 2_745 ?
N5 O1 K1 101.32(17) . 2_745 ?
N5 O1 K1 100.16(18) . . ?
K1 O2 K1 85.76(6) . 1_455 ?
N5 O2 K1 115.51(18) . 1_455 ?
N5 O2 K1 93.24(17) . . ?
K1 N1 H1 75(4) 1_556 . ?
N2 N1 K1 72.55(16) . 1_556 ?
N2 N1 H1 122(4) . . ?
C1 N1 K1 118.41(19) . 1_556 ?
C1 N1 H1 129(4) . . ?
C1 N1 N2 109.3(3) . . ?
K1 N2 K1 84.55(7) 1_456 1_556 ?
N1 N2 K1 83.52(18) . 1_556 ?
N1 N2 K1 136.8(2) . 1_456 ?
C2 N2 K1 116.0(2) . 1_556 ?
C2 N2 K1 120.2(2) . 1_456 ?
C2 N2 N1 102.3(3) . . ?
C1 N3 K1 86.71(17) . 2_645 ?
C1 N3 C2 102.5(3) . . ?
C2 N3 K1 130.1(2) . 2_645 ?
K1 N4 K1 86.90(8) 2_745 2_645 ?
N5 N4 K1 125.60(18) . 2_645 ?
N5 N4 K1 96.85(17) . 2_745 ?
N5 N4 C1 117.5(3) . . ?
C1 N4 K1 142.5(2) . 2_745 ?
C1 N4 K1 84.89(17) . 2_645 ?
K1 N5 K1 112.01(7) . 2_745 ?
O1 N5 K1 56.86(15) . . ?
O1 N5 K1 56.41(15) . 2_745 ?
O1 N5 N4 115.3(3) . . ?
O2 N5 K1 63.63(15) . . ?
O2 N5 K1 170.67(19) . 2_745 ?
O2 N5 O1 120.4(3) . . ?
O2 N5 N4 124.3(3) . . ?
N4 N5 K1 171.63(19) . . ?
N4 N5 K1 59.75(15) . 2_745 ?
N1 C1 K1 133.6(2) . 2_645 ?
N1 C1 N4 131.6(3) . . ?
N3 C1 K1 68.93(17) . 2_645 ?
N3 C1 N1 110.1(3) . . ?
N3 C1 N4 118.3(3) . . ?
N4 C1 K1 69.99(16) . 2_645 ?
N2 C2 N3 115.7(3) . . ?
N2 C2 H2 122.1 . . ?
N3 C2 H2 122.1 . . ?

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 O2 0.79(6) 2.23(5) 2.624(4) 111(4) . yes
N1 H1 N3 0.79(6) 2.20(6) 2.924(4) 153(5) 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
K1 O1 N5 K1 -166.10(13) . . . 2_745 ?
K1 O1 N5 K1 166.10(13) 2_745 . . . ?
K1 O1 N5 O2 3.5(3) . . . . ?
K1 O1 N5 O2 169.6(2) 2_745 . . . ?
K1 O1 N5 N4 -10.4(3) 2_745 . . . ?
K1 O1 N5 N4 -176.5(2) . . . . ?
K1 O2 N5 K1 86.84(12) 1_455 . . . ?
K1 O2 N5 O1 -3.3(3) . . . . ?
K1 O2 N5 O1 83.5(3) 1_455 . . . ?
K1 O2 N5 N4 176.8(2) . . . . ?
K1 O2 N5 N4 -96.4(3) 1_455 . . . ?
K1 N1 N2 K1 74.9(2) 1_556 . . 1_456 ?
K1 N1 N2 C2 -115.2(2) 1_556 . . . ?
K1 N1 C1 K1 160.16(14) 1_556 . . 2_645 ?
K1 N1 C1 N3 80.5(3) 1_556 . . . ?
K1 N1 C1 N4 -97.5(3) 1_556 . . . ?
K1 N2 C2 N3 172.46(19) 1_456 . . . ?
K1 N2 C2 N3 -88.3(3) 1_556 . . . ?
K1 N3 C1 N1 130.3(2) 2_645 . . . ?
K1 N3 C1 N4 -51.4(3) 2_645 . . . ?
K1 N3 C2 N2 -96.5(3) 2_645 . . . ?
K1 N4 N5 K1 -91.08(18) 2_645 . . 2_745 ?
K1 N4 N5 O1 -81.0(3) 2_645 . . . ?
K1 N4 N5 O1 10.0(2) 2_745 . . . ?
K1 N4 N5 O2 98.9(3) 2_645 . . . ?
K1 N4 N5 O2 -170.0(2) 2_745 . . . ?
K1 N4 C1 K1 -78.1(3) 2_745 . . 2_645 ?
K1 N4 C1 N1 -131.2(3) 2_645 . . . ?
K1 N4 C1 N1 150.7(3) 2_745 . . . ?
K1 N4 C1 N3 50.9(3) 2_645 . . . ?
K1 N4 C1 N3 -27.2(5) 2_745 . . . ?
N1 N2 C2 N3 0.4(4) . . . . ?
N2 N1 C1 K1 80.0(3) . . . 2_645 ?
N2 N1 C1 N3 0.4(3) . . . . ?
N2 N1 C1 N4 -177.6(3) . . . . ?
N5 N4 C1 K1 127.8(3) . . . 2_645 ?
N5 N4 C1 N1 -3.4(5) . . . . ?
N5 N4 C1 N3 178.7(3) . . . . ?
C1 N1 N2 K1 114.7(2) . . . 1_556 ?
C1 N1 N2 K1 -170.4(2) . . . 1_456 ?
C1 N1 N2 C2 -0.5(3) . . . . ?
C1 N3 C2 N2 -0.2(4) . . . . ?
C1 N4 N5 K1 164.5(3) . . . 2_745 ?
C1 N4 N5 O1 174.5(2) . . . . ?
C1 N4 N5 O2 -5.6(4) . . . . ?
C2 N3 C1 K1 -130.4(2) . . . 2_645 ?
C2 N3 C1 N1 -0.1(3) . . . . ?
C2 N3 C1 N4 178.2(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id SOHAN-800-K
_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_js122f
_database_code_depnum_ccdc_archive 'CCDC 2296316'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_audit_creation_date             2022-01-31
_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         'C6 H12 N4 O2'
_chemical_formula_sum            'C6 H12 N4 O2'
_chemical_formula_weight         172.20
_chemical_melting_point          423
_chemical_oxdiff_formula         C6H12N4O2
_chemical_oxdiff_usercomment     SOHAN-45
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.80690(8)
_cell_length_b                   5.75687(6)
_cell_length_c                   17.86698(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.2689(9)
_cell_angle_gamma                90
_cell_volume                     800.773(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5130
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.8210
_cell_measurement_theta_min      4.9530
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.677
_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    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0700
-1 0 0 0.1170
0 1 0 0.1144
0 -1 0 0.1211
0 0 -1 0.0364
0 0 1 0.0268
-1 -1 0 0.1331
-1 0 1 0.1112
1 0 -1 0.0723

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.064
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
0.9999 -0.0002 -0.0001 0.0015 -0.1233 0.1547
-0.9996 -0.0001 -0.0002 -0.0015 0.1232 -0.1547
-0.0007 0.9999 0.0005 0.0340 0.2078 0.1651
-0.0008 -1.0000 0.0001 -0.0341 -0.2076 -0.1653
-0.0001 -0.0003 -1.0000 0.0855 -0.0042 -0.0125
0.0007 -0.0004 0.9986 -0.0854 0.0040 0.0124
-0.9990 -1.0003 0.0046 -0.0360 -0.0846 -0.3198
-1.0016 -0.0004 0.9991 -0.0869 0.1276 -0.1427
1.0004 -0.0010 -0.9988 0.0869 -0.1277 0.1423

_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.992
_diffrn_reflns_theta_min         4.964
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  13.00   0.50    0.05    --   47.62 -19.00  30.00   60
  2  ω    -25.00  23.00   0.50    0.05    --   47.62 -19.00 -30.00   96
  3  ω    -23.00   2.00   0.50    0.05    --   47.62 -19.00-180.00   50
  4  ω    114.00 178.00   0.50    0.08    --  107.19  37.00-180.00  128
  5  ω    132.00 157.00   0.50    0.08    --  107.19  57.00 -30.00   50
  6  ω     37.00  62.00   0.50    0.08    --  107.19 -57.00 -60.00   50
  7  ω     65.00 104.00   0.50    0.08    --  107.19 -99.00-120.00   78
  8  ω     76.00 101.00   0.50    0.08    --  107.19-125.00  30.00   50
  9  ω     43.00  71.00   0.50    0.08    --  107.19-125.00  30.00   56
 10  ω     71.00 104.00   0.50    0.08    --  107.19 -99.00 -60.00   66
 11  ω     64.00 104.00   0.50    0.08    --  107.19 -99.00-180.00   80
 12  ω     74.00 100.00   0.50    0.08    --  107.19 -99.00 120.00   52
 13  ω     77.00 105.00   0.50    0.08    --  107.19 -77.00 150.00   56
 14  ω     36.00  62.00   0.50    0.08    --  107.19 -77.00 150.00   52
 15  ω     35.00  85.00   0.50    0.08    --  107.19 -99.00 150.00  100
 16  ω     50.00 104.00   0.50    0.08    --  107.19 -99.00  60.00  108
 17  ω     43.00  90.00   0.50    0.08    --  107.19 -99.00  30.00   94
 18  ω    -24.00  16.00   0.50    0.05    --  -47.62  19.00-180.00   80
 19  ω    -69.00   0.00   0.50    0.05    --  -47.62  77.00-180.00  138
 20  ω    -61.00  -9.00   0.50    0.05    --  -47.62  57.00  60.00  104
 21  ω    -43.00  26.00   0.50    0.05    --  -47.62  37.00 120.00  138
 22  ω    -67.00 -26.00   0.50    0.08    --  -91.75  57.00 -30.00   82
 23  ω    -67.00 -32.00   0.50    0.08    --  -91.75  57.00 -60.00   70
 24  ω    -65.00 -25.00   0.50    0.08    --  -91.75  57.00-120.00   80
 25  ω    -46.00 -20.00   0.50    0.08    --  -91.75  57.00-180.00   52
 26  ω   -148.00-123.00   0.50    0.08    --  -91.75 -37.00 -60.00   50
 27  ω   -156.00-131.00   0.50    0.08    --  -91.75 -57.00-120.00   50
 28  ω   -162.00-127.00   0.50    0.08    --  -91.75 -57.00-150.00   70
 29  ω   -163.00-128.00   0.50    0.08    --  -91.75 -57.00-180.00   70
 30  ω   -159.00-131.00   0.50    0.08    --  -91.75 -57.00 -90.00   56
 31  ω   -163.00-130.00   0.50    0.08    --  -91.75 -57.00 -60.00   66
 32  ω   -160.00-131.00   0.50    0.08    --  -91.75 -57.00 -30.00   58
 33  ω   -163.00-138.00   0.50    0.08    --  -91.75 -77.00 120.00   50
 34  ω   -150.00-114.00   0.50    0.08    --  -91.75-125.00 120.00   72
 35  ω   -163.00-137.00   0.50    0.08    --  -91.75 -99.00 -30.00   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      0.0015288000
_diffrn_orient_matrix_UB_12      0.0340815000
_diffrn_orient_matrix_UB_13      -0.0854679000
_diffrn_orient_matrix_UB_21      -0.1233101000
_diffrn_orient_matrix_UB_22      0.2077335000
_diffrn_orient_matrix_UB_23      0.0041367000
_diffrn_orient_matrix_UB_31      0.1547804000
_diffrn_orient_matrix_UB_32      0.1652005000
_diffrn_orient_matrix_UB_33      0.0123958000
_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                1532
_reflns_number_total             1607
_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         0.205
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.074
_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)+(0.0402P)²+0.3186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0820
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
;
_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 0.26858(10) 1.06635(14) 0.49942(4) 0.0182(2) Uani 1 1 d . . . . .
H1 H 0.353(2) 1.149(3) 0.5216(10) 0.036(4) Uiso 1 1 d . . . . .
O2 O 0.61180(10) 0.16293(15) 0.16274(4) 0.0186(2) Uani 1 1 d . . . . .
H2 H 0.719(2) 0.141(3) 0.1554(10) 0.034(4) Uiso 1 1 d . . . . .
N1 N 0.29133(11) 0.43906(16) 0.37024(5) 0.0128(2) Uani 1 1 d . . . . .
N2 N 0.14784(12) 0.29132(17) 0.35837(5) 0.0158(2) Uani 1 1 d . . . . .
H2A H 0.053(2) 0.383(3) 0.3535(8) 0.024(4) Uiso 1 1 d . . . . .
H2B H 0.144(2) 0.198(3) 0.3989(9) 0.026(4) Uiso 1 1 d . . . . .
N3 N 0.47698(11) 0.69288(16) 0.41718(5) 0.0153(2) Uani 1 1 d . . . . .
N4 N 0.54391(11) 0.58506(16) 0.35564(5) 0.0156(2) Uani 1 1 d . . . . .
C1 C 0.32519(13) 0.60273(19) 0.42498(6) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.43040(13) 0.43396(19) 0.32853(6) 0.0143(2) Uani 1 1 d . . . . .
C3 C 0.20316(13) 0.65999(19) 0.48271(6) 0.0146(2) Uani 1 1 d . . . . .
H3A H 0.180916 0.517785 0.511602 0.018 Uiso 1 1 calc R U . . .
H3B H 0.092694 0.710581 0.457036 0.018 Uiso 1 1 calc R U . . .
C4 C 0.26831(14) 0.84891(19) 0.53687(6) 0.0162(2) Uani 1 1 d . . . . .
H4A H 0.193703 0.857840 0.579222 0.019 Uiso 1 1 calc R U . . .
H4B H 0.386227 0.810847 0.557431 0.019 Uiso 1 1 calc R U . . .
C5 C 0.44574(14) 0.2740(2) 0.26388(6) 0.0189(3) Uani 1 1 d . . . . .
H5A H 0.343132 0.291078 0.228283 0.023 Uiso 1 1 calc R U . . .
H5B H 0.449330 0.111686 0.282202 0.023 Uiso 1 1 calc R U . . .
C6 C 0.60523(14) 0.3227(2) 0.22331(6) 0.0166(2) Uani 1 1 d . . . . .
H6A H 0.602014 0.483880 0.203931 0.020 Uiso 1 1 calc R U . . .
H6B H 0.708792 0.305269 0.258340 0.020 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.881(19) . ?
O1 C4 1.4194(13) . ?
O2 H2 0.869(19) . ?
O2 C6 1.4241(13) . ?
N1 N2 1.4099(12) . ?
N1 C1 1.3695(14) . ?
N1 C2 1.3621(13) . ?
N2 H2A 0.909(16) . ?
N2 H2B 0.906(17) . ?
N3 N4 1.3974(12) . ?
N3 C1 1.3106(14) . ?
N4 C2 1.3086(14) . ?
C1 C3 1.4922(14) . ?
C2 C5 1.4889(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5181(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5128(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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
C4 O1 H1 107.0(11) . . ?
C6 O2 H2 107.4(11) . . ?
C1 N1 N2 129.16(9) . . ?
C2 N1 N2 124.15(9) . . ?
C2 N1 C1 106.63(9) . . ?
N1 N2 H2A 107.2(10) . . ?
N1 N2 H2B 108.0(10) . . ?
H2A N2 H2B 110.5(14) . . ?
C1 N3 N4 107.56(9) . . ?
C2 N4 N3 107.69(8) . . ?
N1 C1 C3 123.12(9) . . ?
N3 C1 N1 108.94(9) . . ?
N3 C1 C3 127.94(10) . . ?
N1 C2 C5 123.45(9) . . ?
N4 C2 N1 109.18(9) . . ?
N4 C2 C5 127.36(10) . . ?
C1 C3 H3A 108.9 . . ?
C1 C3 H3B 108.9 . . ?
C1 C3 C4 113.45(9) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
O1 C4 C3 110.09(9) . . ?
O1 C4 H4A 109.6 . . ?
O1 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
C2 C5 H5A 109.2 . . ?
C2 C5 H5B 109.2 . . ?
C2 C5 C6 111.95(9) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
O2 C6 C5 108.78(9) . . ?
O2 C6 H6A 109.9 . . ?
O2 C6 H6B 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?

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 N3 0.881(19) 1.891(19) 2.7653(12) 171.3(17) 3_676 yes
O2 H2 N4 0.869(19) 1.901(19) 2.7686(12) 176.9(16) 2_645 yes
N2 H2A O2 0.909(16) 2.068(16) 2.9519(13) 163.8(14) 2 yes
N2 H2B O1 0.906(17) 2.116(16) 2.9264(13) 148.5(14) 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C3 C4 -179.37(9) . . . . ?
N1 C2 C5 C6 174.30(10) . . . . ?
N2 N1 C1 N3 177.12(10) . . . . ?
N2 N1 C1 C3 -2.67(17) . . . . ?
N2 N1 C2 N4 -177.30(9) . . . . ?
N2 N1 C2 C5 1.41(16) . . . . ?
N3 N4 C2 N1 -0.02(12) . . . . ?
N3 N4 C2 C5 -178.67(10) . . . . ?
N3 C1 C3 C4 0.88(16) . . . . ?
N4 N3 C1 N1 0.02(12) . . . . ?
N4 N3 C1 C3 179.80(10) . . . . ?
N4 C2 C5 C6 -7.23(16) . . . . ?
C1 N1 C2 N4 0.03(12) . . . . ?
C1 N1 C2 C5 178.74(10) . . . . ?
C1 N3 N4 C2 0.00(12) . . . . ?
C1 C3 C4 O1 70.24(12) . . . . ?
C2 N1 C1 N3 -0.03(12) . . . . ?
C2 N1 C1 C3 -179.83(10) . . . . ?
C2 C5 C6 O2 179.65(9) . . . . ?

_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 SOHAN-45
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.863
