# 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_js721c
_database_code_depnum_ccdc_archive 'CCDC 2154055'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 K N5 O4'
_chemical_formula_sum            'C6 H6 K N5 O4'
_chemical_formula_weight         251.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H6KN5O4
_chemical_oxdiff_usercomment     A70
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.0180(2)
_cell_length_b                   12.9201(2)
_cell_length_c                   8.26330(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.5690(12)
_cell_angle_gamma                90
_cell_volume                     1914.57(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8003
_cell_measurement_temperature    99.98(15)
_cell_measurement_theta_max      79.3110
_cell_measurement_theta_min      4.1910
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.414
_exptl_absorpt_coefficient_mu    5.024
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0503
0 1 0 0.0733
3 -5 4 0.0719
-4 4 -4 0.0872
-12 0 0 0.0195
0 4 5 0.0858
-1 -4 -5 0.0819
12 -1 0 0.0127

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.04
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
-0.0014 -1.0010 -0.0003 -0.0463 0.1099 -0.0050
0.0014 1.0010 0.0003 0.0463 -0.1099 0.0050
3.4528 -5.0813 3.7915 -0.2196 0.5275 -0.8207
-3.7827 4.0725 -4.1687 0.1725 -0.4133 0.8941
-11.6085 0.1219 -0.1277 -0.8118 -0.3355 0.4778
-0.2295 4.4687 4.5264 -0.0847 -0.6494 -0.7558
-0.6953 -3.6615 -4.7616 0.0705 0.5426 0.8370
11.5756 -0.9031 -0.0170 0.7822 0.4253 -0.4553

_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.625
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(15)
_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 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    135.00 170.00   0.50    0.11    --  113.25  77.00  90.00   70
  2  ω    135.00 177.00   0.50    0.11    --  113.25  77.00  60.00   84
  3  ω    122.00 177.00   0.50    0.11    --  113.25  45.00 150.00  110
  4  ω    128.00 161.00   0.50    0.11    --  113.25  45.00  60.00   66
  5  ω    102.00 160.00   0.50    0.11    --  113.25  30.00  30.00  116
  6  ω    146.00 174.00   0.50    0.11    --  113.25  77.00 -90.00   56
  7  ω    127.00 171.00   0.50    0.11    --  113.25  61.00-120.00   88
  8  ω    129.00 164.00   0.50    0.11    --  113.25  77.00-150.00   70
  9  ω    152.00 178.00   0.50    0.11    --  113.25  15.00 -90.00   52
 10  ω    102.00 136.00   0.50    0.11    --  113.25  15.00 -90.00   68
 11  ω    -20.00  24.00   0.50    0.05    --  -47.36  37.00  90.00   88
 12  ω    -17.00  27.00   0.50    0.05    --  -47.36  19.00 150.00   88
 13  ω    -25.00  23.00   0.50    0.05    --  -47.36  19.00  60.00   96
 14  ω    -21.00   5.00   0.50    0.05    --  -47.36  19.00   0.00   52
 15  ω    -25.00  27.00   0.50    0.05    --  -47.36  19.00 -30.00  104
 16  ω    -24.00   6.00   0.50    0.05    --  -47.36  37.00-180.00   60
 17  ω    -40.00  -7.00   0.50    0.05    --  -47.36  37.00-120.00   66
 18  ω     63.00 102.00   0.50    0.05    --   47.36-140.00 -96.00   78
 19  ω     58.00  83.00   0.50    0.11    --  113.25-140.00 -96.00   50
 20  ω     43.00  75.00   0.50    0.11    --  113.25-125.00 -90.00   64
 21  ω     71.00 102.00   0.50    0.11    --  113.25-125.00 -30.00   62
 22  ω     52.00  77.00   0.50    0.11    --  113.25-129.00  76.00   50
 23  ω     46.00  76.00   0.50    0.11    --  113.25-125.00 120.00   60
 24  ω     82.00 107.00   0.50    0.11    --  113.25-125.00 120.00   50
 25  ω     59.00  90.00   0.50    0.05    --   47.36-129.00  76.00   62
 26  ω     53.00 104.00   0.50    0.11    --  113.25 -99.00  17.44  102
 27  ω     74.00 102.00   0.50    0.11    --  113.25 -94.00-120.00   56
 28  ω     75.00 100.00   0.50    0.11    --  113.25 -94.00 -30.00   50
 29  ω     43.00  69.00   0.50    0.11    --  113.25 -94.00 -30.00   52
 30  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00-150.00  124
 31  ω     44.00 104.00   0.50    0.11    --  113.25 -94.00-180.00  120
 32  ω     43.00  69.00   0.50    0.11    --  113.25 -94.00   0.00   52
 33  ω     43.00  68.00   0.50    0.11    --  113.25 -94.00  30.00   50
 34  ω     75.00 103.00   0.50    0.11    --  113.25 -94.00  30.00   56
 35  ω     64.00 104.00   0.50    0.11    --  113.25 -94.00  60.00   80
 36  ω     47.00 104.00   0.50    0.11    --  113.25 -94.00 120.00  114
 37  ω     61.00 103.00   0.50    0.11    --  113.25 -94.00 150.00   84
 38  ω     55.00 104.00   0.50    0.11    --  113.25 -94.00 -60.00   98
 39  ω     42.00  67.00   0.50    0.11    --  113.25 -61.00-120.00   50
 40  ω     43.00  70.00   0.50    0.11    --  113.25 -61.00-150.00   54
 41  ω     43.00  68.00   0.50    0.11    --  113.25 -61.00 -60.00   50
 42  ω     42.00  67.00   0.50    0.11    --  113.25 -61.00  30.00   50
 43  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00  90.00   54
 44  ω     45.00  70.00   0.50    0.11    --  113.25 -61.00 150.00   50
 45  ω     42.00  68.00   0.50    0.11    --  113.25 -61.00 120.00   52
 46  ω     44.00  70.00   0.50    0.11    --  113.25 -61.00  60.00   52
 47  ω     95.00 129.00   0.50    0.11    --  113.25 140.00 -37.00   68
 48  ω    124.00 149.00   0.50    0.11    --  113.25 129.00 149.00   50
 49  ω    -22.00  23.00   0.50    0.05    --   47.36 -19.00 150.00   90
 50  ω    -71.00 -43.00   0.50    0.05    --  -47.36 129.00 149.00   56
 51  ω    -76.00 -51.00   0.50    0.11    --  -91.75 129.00 149.00   50
 52  ω    -82.00 -56.00   0.50    0.05    --  -47.36 140.00 -37.00   52
 53  ω    -89.00 -58.00   0.50    0.11    --  -91.75 140.00 -37.00   62
 54  ω    -52.00 -22.00   0.50    0.11    --  -91.75  45.00 -60.00   60
 55  ω    -51.00 -23.00   0.50    0.11    --  -91.75  45.00 -30.00   56
 56  ω   -160.00-127.00   0.50    0.11    --  -91.75 -61.00  30.00   66
 57  ω   -155.00-129.00   0.50    0.11    --  -91.75 -45.00   0.00   52
 58  ω   -113.00 -73.00   0.50    0.05    --  -47.36-129.00  76.00   80
 59  ω   -137.00-112.00   0.50    0.11    --  -91.75-129.00  76.00   50
 60  ω   -115.00 -66.00   0.50    0.05    --  -47.36-140.00 -96.00   98
 61  ω   -110.00 -70.00   0.50    0.11    --  -91.75-140.00 -96.00   80
 62  ω   -161.00-127.00   0.50    0.11    --  -91.75 -61.00-150.00   68
;
_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      0.0710892000
_diffrn_orient_matrix_UB_12      0.0462137000
_diffrn_orient_matrix_UB_13      -0.0607308000
_diffrn_orient_matrix_UB_21      0.0281207000
_diffrn_orient_matrix_UB_22      -0.1098020000
_diffrn_orient_matrix_UB_23      -0.0336317000
_diffrn_orient_matrix_UB_31      -0.0391955000
_diffrn_orient_matrix_UB_32      0.0050705000
_diffrn_orient_matrix_UB_33      -0.1739593000
_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                1967
_reflns_number_total             2054
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.068
_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)+(0.0436P)²+1.7427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0808
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_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 0.500000 0.46446(3) 0.750000 0.01445(13) Uani 1 2 d S T P . .
K2 K 0.500000 0.07968(3) 0.750000 0.01615(13) Uani 1 2 d S T P . .
O1 O 0.58694(6) 0.39791(8) 0.48978(12) 0.0166(2) Uani 1 1 d . . . . .
O2 O 0.55128(6) 0.26359(8) 0.62185(12) 0.0163(2) Uani 1 1 d . . . . .
O3 O 0.56205(7) 0.08421(8) 0.46879(13) 0.0214(2) Uani 1 1 d . . . . .
O4 O 0.60370(6) 0.09695(8) 0.23083(13) 0.0199(2) Uani 1 1 d . . . . .
N1 N 0.70551(7) 0.30013(9) 0.24558(14) 0.0140(2) Uani 1 1 d . . . . .
N2 N 0.58280(7) 0.33571(10) 0.12178(14) 0.0148(3) Uani 1 1 d . . . . .
N3 N 0.61130(7) 0.38102(10) -0.00561(14) 0.0146(2) Uani 1 1 d . . . . .
N4 N 0.57734(7) 0.30105(10) 0.50092(14) 0.0135(2) Uani 1 1 d . . . . .
N5 N 0.58688(7) 0.13825(10) 0.36084(14) 0.0149(2) Uani 1 1 d . . . . .
C1 C 0.59742(8) 0.24323(11) 0.37285(17) 0.0138(3) Uani 1 1 d . . . . .
C2 C 0.63058(8) 0.29622(11) 0.23801(17) 0.0132(3) Uani 1 1 d . . . . .
C3 C 0.73348(8) 0.34867(11) 0.12391(16) 0.0131(3) Uani 1 1 d . . . . .
C4 C 0.68468(8) 0.38832(11) -0.00705(16) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.81608(8) 0.36376(12) 0.13200(18) 0.0169(3) Uani 1 1 d . . . . .
H5A H 0.828249 0.435882 0.160113 0.025 Uiso 1 1 calc R U . . .
H5B H 0.833383 0.347410 0.026114 0.025 Uiso 1 1 calc R U . . .
H5C H 0.840704 0.317885 0.215076 0.025 Uiso 1 1 calc R U . . .
C6 C 0.71337(9) 0.44121(13) -0.14923(18) 0.0197(3) Uani 1 1 d . . . . .
H6A H 0.671492 0.458728 -0.229193 0.030 Uiso 1 1 calc R U . . .
H6B H 0.747727 0.394955 -0.199200 0.030 Uiso 1 1 calc R U . . .
H6C H 0.739706 0.504622 -0.112568 0.030 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 2.9104(10) 2_656 ?
K1 O1 2.9898(11) 5_666 ?
K1 O1 2.9898(11) 6_566 ?
K1 O1 2.9104(10) . ?
K1 O2 2.9834(11) . ?
K1 O2 2.9834(11) 2_656 ?
K1 N2 3.2127(13) 5_666 ?
K1 N2 3.2127(13) 6_566 ?
K1 N3 2.9113(12) 2_655 ?
K1 N3 2.9113(12) 1_556 ?
K1 N4 3.3455(12) 2_656 ?
K1 N4 3.3455(12) . ?
K2 O2 2.7949(11) . ?
K2 O2 2.7948(11) 2_656 ?
K2 O3 2.9343(12) 5_656 ?
K2 O3 2.6753(11) 2_656 ?
K2 O3 2.6753(11) . ?
K2 O3 2.9343(12) 6_556 ?
K2 O4 2.9634(11) 5_656 ?
K2 O4 2.9634(11) 6_556 ?
K2 N5 3.3075(13) 6_556 ?
K2 N5 3.3075(13) 5_656 ?
K2 C5 3.4409(14) 8_456 ?
K2 C5 3.4409(14) 7_656 ?
O1 N4 1.2679(16) . ?
O2 N4 1.2427(16) . ?
O3 N5 1.2493(16) . ?
O4 N5 1.2625(16) . ?
N1 C2 1.3465(19) . ?
N1 C3 1.3253(18) . ?
N2 N3 1.3489(17) . ?
N2 C2 1.3279(18) . ?
N3 C4 1.3268(19) . ?
N4 C1 1.3724(18) . ?
N5 C1 1.3719(19) . ?
C1 C2 1.4820(19) . ?
C3 C4 1.4219(19) . ?
C3 C5 1.4959(19) . ?
C4 C6 1.4941(19) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 O1 145.63(4) 2_656 . ?
O1 K1 O1 107.01(4) 6_566 5_666 ?
O1 K1 O1 112.36(4) 2_656 5_666 ?
O1 K1 O1 88.34(3) 2_656 6_566 ?
O1 K1 O1 112.36(4) . 6_566 ?
O1 K1 O1 88.34(3) . 5_666 ?
O1 K1 O2 43.39(3) . . ?
O1 K1 O2 102.28(3) 2_656 . ?
O1 K1 O2 43.39(3) 2_656 2_656 ?
O1 K1 O2 102.28(3) . 2_656 ?
O1 K1 N2 141.40(3) . 5_666 ?
O1 K1 N2 62.20(3) 5_666 6_566 ?
O1 K1 N2 72.14(3) 2_656 5_666 ?
O1 K1 N2 60.68(3) 5_666 5_666 ?
O1 K1 N2 62.20(3) 6_566 5_666 ?
O1 K1 N2 141.40(3) 2_656 6_566 ?
O1 K1 N2 72.14(3) . 6_566 ?
O1 K1 N2 60.68(3) 6_566 6_566 ?
O1 K1 N3 91.10(3) 2_656 2_655 ?
O1 K1 N3 76.23(3) 2_656 1_556 ?
O1 K1 N3 76.23(3) . 2_655 ?
O1 K1 N3 91.10(3) . 1_556 ?
O1 K1 N4 22.00(3) . . ?
O1 K1 N4 124.08(3) 5_666 2_656 ?
O1 K1 N4 123.66(3) 2_656 . ?
O1 K1 N4 100.97(3) 5_666 . ?
O1 K1 N4 124.08(3) 6_566 . ?
O1 K1 N4 123.66(3) . 2_656 ?
O1 K1 N4 100.97(3) 6_566 2_656 ?
O1 K1 N4 22.00(3) 2_656 2_656 ?
O2 K1 O1 116.27(3) . 5_666 ?
O2 K1 O1 116.27(3) 2_656 6_566 ?
O2 K1 O1 126.32(3) 2_656 5_666 ?
O2 K1 O1 126.31(3) . 6_566 ?
O2 K1 O2 59.10(4) . 2_656 ?
O2 K1 N2 114.35(3) 2_656 5_666 ?
O2 K1 N2 170.37(3) . 5_666 ?
O2 K1 N2 170.37(3) 2_656 6_566 ?
O2 K1 N2 114.35(3) . 6_566 ?
O2 K1 N4 80.28(3) 2_656 . ?
O2 K1 N4 21.69(3) . . ?
O2 K1 N4 21.69(3) 2_656 2_656 ?
O2 K1 N4 80.28(3) . 2_656 ?
N2 K1 N2 73.04(4) 6_566 5_666 ?
N2 K1 N4 160.83(3) 5_666 . ?
N2 K1 N4 94.00(3) 6_566 . ?
N2 K1 N4 94.00(3) 5_666 2_656 ?
N2 K1 N4 160.83(3) 6_566 2_656 ?
N3 K1 O1 58.62(3) 2_655 5_666 ?
N3 K1 O1 58.62(3) 1_556 6_566 ?
N3 K1 O1 164.00(3) 1_556 5_666 ?
N3 K1 O1 164.00(3) 2_655 6_566 ?
N3 K1 O2 69.38(3) 2_655 . ?
N3 K1 O2 73.01(3) 1_556 . ?
N3 K1 O2 69.38(3) 1_556 2_656 ?
N3 K1 O2 73.01(3) 2_655 2_656 ?
N3 K1 N2 112.30(3) 2_655 6_566 ?
N3 K1 N2 112.30(3) 1_556 5_666 ?
N3 K1 N2 102.46(3) 2_655 5_666 ?
N3 K1 N2 102.46(3) 1_556 6_566 ?
N3 K1 N3 136.53(5) 2_655 1_556 ?
N3 K1 N4 68.87(3) 2_655 . ?
N3 K1 N4 83.86(3) 1_556 . ?
N3 K1 N4 83.86(3) 2_655 2_656 ?
N3 K1 N4 68.87(3) 1_556 2_656 ?
N4 K1 N4 101.74(4) 2_656 . ?
O2 K2 O2 63.53(4) 2_656 . ?
O2 K2 O3 120.02(3) . 5_656 ?
O2 K2 O3 136.62(3) . 6_556 ?
O2 K2 O3 136.62(3) 2_656 5_656 ?
O2 K2 O3 120.02(3) 2_656 6_556 ?
O2 K2 O4 155.28(3) . 5_656 ?
O2 K2 O4 113.65(3) . 6_556 ?
O2 K2 O4 155.27(3) 2_656 6_556 ?
O2 K2 O4 113.65(3) 2_656 5_656 ?
O2 K2 N5 141.61(3) . 5_656 ?
O2 K2 N5 131.58(3) . 6_556 ?
O2 K2 N5 141.61(3) 2_656 6_556 ?
O2 K2 N5 131.58(3) 2_656 5_656 ?
O2 K2 C5 93.26(3) 2_656 7_656 ?
O2 K2 C5 65.30(3) . 7_656 ?
O2 K2 C5 65.30(3) 2_656 8_456 ?
O2 K2 C5 93.26(3) . 8_456 ?
O3 K2 O2 119.47(3) 2_656 . ?
O3 K2 O2 58.06(3) 2_656 2_656 ?
O3 K2 O2 58.06(3) . . ?
O3 K2 O2 119.47(3) . 2_656 ?
O3 K2 O3 112.62(3) . 6_556 ?
O3 K2 O3 87.62(5) 5_656 6_556 ?
O3 K2 O3 177.49(5) . 2_656 ?
O3 K2 O3 112.62(3) 2_656 5_656 ?
O3 K2 O3 69.33(4) . 5_656 ?
O3 K2 O3 69.33(4) 2_656 6_556 ?
O3 K2 O4 43.34(3) 5_656 5_656 ?
O3 K2 O4 112.46(3) . 5_656 ?
O3 K2 O4 67.41(3) 5_656 6_556 ?
O3 K2 O4 67.41(3) 6_556 5_656 ?
O3 K2 O4 69.61(3) 2_656 5_656 ?
O3 K2 O4 43.34(3) 6_556 6_556 ?
O3 K2 O4 112.47(3) 2_656 6_556 ?
O3 K2 O4 69.61(3) . 6_556 ?
O3 K2 N5 22.06(3) 5_656 5_656 ?
O3 K2 N5 91.87(3) . 6_556 ?
O3 K2 N5 91.87(3) 2_656 5_656 ?
O3 K2 N5 72.43(3) 5_656 6_556 ?
O3 K2 N5 90.26(3) 2_656 6_556 ?
O3 K2 N5 22.06(3) 6_556 6_556 ?
O3 K2 N5 72.43(3) 6_556 5_656 ?
O3 K2 N5 90.26(3) . 5_656 ?
O3 K2 C5 76.66(4) . 7_656 ?
O3 K2 C5 102.79(4) . 8_456 ?
O3 K2 C5 71.32(3) 5_656 8_456 ?
O3 K2 C5 102.79(4) 2_656 7_656 ?
O3 K2 C5 76.66(4) 2_656 8_456 ?
O3 K2 C5 128.81(4) 6_556 8_456 ?
O3 K2 C5 71.32(3) 6_556 7_656 ?
O3 K2 C5 128.81(3) 5_656 7_656 ?
O4 K2 O4 79.28(4) 5_656 6_556 ?
O4 K2 N5 67.27(3) 6_556 5_656 ?
O4 K2 N5 22.37(3) 6_556 6_556 ?
O4 K2 N5 22.37(3) 5_656 5_656 ?
O4 K2 N5 67.27(3) 5_656 6_556 ?
O4 K2 C5 65.40(3) 5_656 8_456 ?
O4 K2 C5 65.40(3) 6_556 7_656 ?
O4 K2 C5 138.01(4) 5_656 7_656 ?
O4 K2 C5 138.01(4) 6_556 8_456 ?
N5 K2 N5 63.29(4) 5_656 6_556 ?
N5 K2 C5 132.55(3) 6_556 8_456 ?
N5 K2 C5 71.66(3) 6_556 7_656 ?
N5 K2 C5 132.55(3) 5_656 7_656 ?
N5 K2 C5 71.66(3) 5_656 8_456 ?
C5 K2 C5 155.48(5) 7_656 8_456 ?
K1 O1 K1 91.66(3) . 5_666 ?
N4 O1 K1 98.68(8) . . ?
N4 O1 K1 124.67(8) . 5_666 ?
K2 O2 K1 118.68(4) . . ?
N4 O2 K1 95.79(8) . . ?
N4 O2 K2 143.17(9) . . ?
K2 O3 K2 110.67(4) . 5_656 ?
N5 O3 K2 147.27(9) . . ?
N5 O3 K2 96.02(8) . 5_656 ?
N5 O4 K2 94.32(8) . 5_656 ?
C3 N1 C2 115.84(12) . . ?
N3 N2 K1 97.63(8) . 5_666 ?
C2 N2 K1 111.07(9) . 5_666 ?
C2 N2 N3 117.52(12) . . ?
N2 N3 K1 114.41(8) . 1_554 ?
C4 N3 K1 125.97(9) . 1_554 ?
C4 N3 N2 119.54(12) . . ?
O1 N4 K1 59.31(7) . . ?
O1 N4 C1 115.67(12) . . ?
O2 N4 K1 62.52(7) . . ?
O2 N4 O1 120.51(12) . . ?
O2 N4 C1 123.82(12) . . ?
C1 N4 K1 167.08(9) . . ?
O3 N5 K2 61.92(7) . 5_656 ?
O3 N5 O4 120.24(12) . . ?
O3 N5 C1 123.89(12) . . ?
O4 N5 K2 63.31(7) . 5_656 ?
O4 N5 C1 115.87(12) . . ?
C1 N5 K2 156.96(9) . 5_656 ?
N4 C1 C2 118.95(13) . . ?
N5 C1 N4 123.29(13) . . ?
N5 C1 C2 117.74(12) . . ?
N1 C2 C1 117.25(12) . . ?
N2 C2 N1 126.58(13) . . ?
N2 C2 C1 116.16(12) . . ?
N1 C3 C4 119.68(13) . . ?
N1 C3 C5 118.53(12) . . ?
C4 C3 C5 121.74(13) . . ?
N3 C4 C3 120.72(13) . . ?
N3 C4 C6 117.43(12) . . ?
C3 C4 C6 121.84(13) . . ?
K2 C5 H5A 62.8 7_656 . ?
K2 C5 H5B 85.3 7_656 . ?
K2 C5 H5C 64.6 7_656 . ?
C3 C5 K2 165.22(10) . 7_656 ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O1 N4 K1 -98.12(8) 5_666 . . . ?
K1 O1 N4 O2 -13.51(13) . . . . ?
K1 O1 N4 O2 -111.63(11) 5_666 . . . ?
K1 O1 N4 C1 166.48(10) . . . . ?
K1 O1 N4 C1 68.36(14) 5_666 . . . ?
K1 O2 N4 O1 13.09(12) . . . . ?
K1 O2 N4 C1 -166.90(11) . . . . ?
K1 N2 N3 K1 -61.23(7) 5_666 . . 1_554 ?
K1 N2 N3 C4 115.81(12) 5_666 . . . ?
K1 N2 C2 N1 -108.35(13) 5_666 . . . ?
K1 N2 C2 C1 71.25(13) 5_666 . . . ?
K1 N3 C4 C3 176.85(9) 1_554 . . . ?
K1 N3 C4 C6 -2.04(18) 1_554 . . . ?
K1 N4 C1 N5 -112.1(4) . . . . ?
K1 N4 C1 C2 66.4(5) . . . . ?
K2 O2 N4 K1 160.06(15) . . . . ?
K2 O2 N4 O1 173.14(10) . . . . ?
K2 O2 N4 C1 -6.8(2) . . . . ?
K2 O3 N5 K2 -145.12(18) . . . 5_656 ?
K2 O3 N5 O4 -170.93(12) . . . . ?
K2 O3 N5 O4 -25.81(13) 5_656 . . . ?
K2 O3 N5 C1 153.91(12) 5_656 . . . ?
K2 O3 N5 C1 8.8(3) . . . . ?
K2 O4 N5 O3 25.47(13) 5_656 . . . ?
K2 O4 N5 C1 -154.27(10) 5_656 . . . ?
K2 N5 C1 N4 93.3(2) 5_656 . . . ?
K2 N5 C1 C2 -85.2(3) 5_656 . . . ?
O1 N4 C1 N5 -176.21(13) . . . . ?
O1 N4 C1 C2 2.28(18) . . . . ?
O2 N4 C1 N5 3.8(2) . . . . ?
O2 N4 C1 C2 -177.73(12) . . . . ?
O3 N5 C1 N4 -4.2(2) . . . . ?
O3 N5 C1 C2 177.27(13) . . . . ?
O4 N5 C1 N4 175.51(13) . . . . ?
O4 N5 C1 C2 -3.00(19) . . . . ?
N1 C3 C4 N3 2.8(2) . . . . ?
N1 C3 C4 C6 -178.38(13) . . . . ?
N1 C3 C5 K2 -48.1(4) . . . 7_656 ?
N2 N3 C4 C3 0.2(2) . . . . ?
N2 N3 C4 C6 -178.71(13) . . . . ?
N3 N2 C2 N1 2.8(2) . . . . ?
N3 N2 C2 C1 -177.58(12) . . . . ?
N4 C1 C2 N1 94.45(16) . . . . ?
N4 C1 C2 N2 -85.20(16) . . . . ?
N5 C1 C2 N1 -86.98(16) . . . . ?
N5 C1 C2 N2 93.38(16) . . . . ?
C2 N1 C3 C4 -2.81(19) . . . . ?
C2 N1 C3 C5 174.81(12) . . . . ?
C2 N2 N3 K1 -179.83(9) . . . 1_554 ?
C2 N2 N3 C4 -2.79(19) . . . . ?
C3 N1 C2 N2 0.1(2) . . . . ?
C3 N1 C2 C1 -179.52(12) . . . . ?
C4 C3 C5 K2 129.5(3) . . . 7_656 ?
C5 C3 C4 N3 -174.77(13) . . . . ?
C5 C3 C4 C6 4.1(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'A70 Block'
_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 1.757
_oxdiff_exptl_absorpt_empirical_full_min 0.645
####################################################################### 
# 
# 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_js1121c
_database_code_depnum_ccdc_archive 'CCDC 2154057'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-11-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N5 O4, H4 N'
_chemical_formula_sum            'C6 H10 N6 O4'
_chemical_formula_weight         230.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H10N6O4
_chemical_oxdiff_usercomment     A95
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                   5.96567(19)
_cell_length_b                   7.3226(2)
_cell_length_c                   11.8671(4)
_cell_angle_alpha                77.154(3)
_cell_angle_beta                 81.278(3)
_cell_angle_gamma                81.757(3)
_cell_volume                     496.34(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3625
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5550
_cell_measurement_theta_min      3.8420
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0858
1 0 0 0.0751
0 -1 -1 0.0458
0 0 1 0.0493
0 0 -1 0.0341
3 2 -3 0.0602
0 4 -3 0.0306
0 -4 4 0.0689
3 -1 5 0.0740
-4 -1 -4 0.0796
0 4 6 0.0567
-4 0 2 0.0817
0 3 -5 0.0221

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.084
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
-1.0058 0.0008 0.0009 0.1134 -0.1322 -0.1991
1.0000 -0.0005 -0.0008 -0.1127 0.1314 0.1980
-0.0019 -1.0014 -1.0026 -0.1514 0.1291 -0.1173
0.0010 0.0009 1.0014 0.1213 0.0570 0.0093
-0.0007 0.0010 -1.0000 -0.1211 -0.0572 -0.0090
2.5888 2.1840 -3.4579 -0.6447 -0.2633 0.7169
0.0095 3.6499 -3.4811 -0.3130 -0.8763 0.3639
0.0446 -3.6216 3.5394 0.3148 0.8815 -0.3496
2.8794 -0.6455 5.1578 0.2814 0.7920 0.5471
-3.5121 -1.3875 -4.2078 -0.1563 -0.4426 -0.8830
-0.1465 3.7330 5.6676 0.8157 -0.3915 0.4244
-3.5976 -0.4711 1.7060 0.5976 -0.2878 -0.7479
0.2326 3.0653 -4.6064 -0.4920 -0.8023 0.3349

_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  0.0271
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5927
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.781
_diffrn_reflns_theta_min         3.850
_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 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    127.00 178.00   0.50    0.07    --  113.25  45.00 -60.00  102
  2  ω    139.00 175.00   0.50    0.07    --  113.25  45.00-120.00   72
  3  ω    143.00 170.00   0.50    0.07    --  113.25  77.00 -90.00   54
  4  ω    145.00 178.00   0.50    0.07    --  113.25  45.00 -30.00   66
  5  ω    122.00 178.00   0.50    0.07    --  113.25  45.00   0.00  112
  6  ω    134.00 175.00   0.50    0.07    --  113.25  77.00 120.00   82
  7  ω    109.00 178.00   0.50    0.07    --  113.25  15.00  60.00  138
  8  ω    -16.00  25.00   0.50    0.05    --   47.89 -19.00-120.00   82
  9  ω    -26.00  -1.00   0.50    0.05    --   47.89 -19.00-150.00   50
 10  ω    -24.00  22.00   0.50    0.05    --   47.89 -19.00 -30.00   92
 11  ω    -15.00  18.00   0.50    0.05    --   47.89 -19.00  30.00   66
 12  ω     -6.00  21.00   0.50    0.05    --   47.89 -19.00  90.00   54
 13  ω    -16.00  24.00   0.50    0.05    --   47.89 -19.00 120.00   80
 14  ω     42.00  68.00   0.50    0.07    --  113.25 -94.00 -30.00   52
 15  ω     58.00  91.00   0.50    0.07    --  113.25-125.00  30.00   66
 16  ω     83.00 123.00   0.50    0.07    --  113.25-145.00  -1.00   80
 17  ω     46.00 104.00   0.50    0.07    --  113.25 -96.00  72.96  116
 18  ω     61.00  90.00   0.50    0.07    --  113.25-125.00 166.00   58
 19  ω     49.00  85.00   0.50    0.05    --   47.89-125.00 166.00   72
 20  ω     42.00  76.00   0.50    0.07    --  113.25 -94.00  60.00   68
 21  ω     45.00 104.00   0.50    0.07    --  113.25 -94.00 120.00  118
 22  ω     68.00  99.00   0.50    0.05    --   47.89-145.00  -1.00   62
 23  ω     79.00 104.00   0.50    0.07    --  113.25 -94.00  90.00   50
 24  ω     78.00 103.00   0.50    0.07    --  113.25 -94.00   0.00   50
 25  ω     77.00 102.00   0.50    0.07    --  113.25 -94.00 -30.00   50
 26  ω     44.00 104.00   0.50    0.07    --  113.25 -94.00-150.00  120
 27  ω     42.00  67.00   0.50    0.07    --  113.25 -61.00-180.00   50
 28  ω     44.00  69.00   0.50    0.07    --  113.25 -61.00-120.00   50
 29  ω     43.00  68.00   0.50    0.07    --  113.25 -61.00 -60.00   50
 30  ω     44.00  69.00   0.50    0.07    --  113.25 -61.00 -90.00   50
 31  ω     44.00  82.00   0.50    0.07    --  113.25 -77.00   0.00   76
 32  ω     44.00  69.00   0.50    0.07    --  113.25 -61.00-150.00   50
 33  ω     42.00  67.00   0.50    0.07    --  113.25 -61.00  60.00   50
 34  ω     45.00  70.00   0.50    0.07    --  113.25 -61.00 120.00   50
 35  ω     42.00  67.00   0.50    0.07    --  113.25 -61.00 150.00   50
 36  ω    131.00 176.00   0.50    0.07    --  113.25 125.00  30.00   90
 37  ω    123.00 170.00   0.50    0.07    --  113.25 125.00   0.00   94
 38  ω     93.00 119.00   0.50    0.07    --  113.25 145.00  51.00   52
 39  ω    113.00 138.00   0.50    0.07    --  113.25 125.00-116.00   50
 40  ω    -23.00  24.00   0.50    0.05    --  -47.89  19.00 120.00   94
 41  ω    -80.00 -55.00   0.50    0.05    --  -47.89 145.00  51.00   50
 42  ω    -85.00 -60.00   0.50    0.07    --  -91.75 145.00  51.00   50
 43  ω    -73.00 -48.00   0.50    0.05    --  -47.89 125.00-116.00   50
 44  ω    -82.00 -30.00   0.50    0.05    --  -47.89 125.00-180.00  104
 45  ω   -133.00 -81.00   0.50    0.07    --  -91.75 -15.00  30.00  104
 46  ω   -125.00 -80.00   0.50    0.07    --  -91.75-125.00 166.00   90
 47  ω   -109.00 -72.00   0.50    0.05    --  -47.89-145.00  -1.00   74
 48  ω   -130.00-105.00   0.50    0.07    --  -91.75-145.00  -1.00   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      -0.1125853000
_diffrn_orient_matrix_UB_12      0.0301225000
_diffrn_orient_matrix_UB_13      0.1211780000
_diffrn_orient_matrix_UB_21      0.1313620000
_diffrn_orient_matrix_UB_22      -0.1861462000
_diffrn_orient_matrix_UB_23      0.0569314000
_diffrn_orient_matrix_UB_31      0.1980414000
_diffrn_orient_matrix_UB_32      0.1077778000
_diffrn_orient_matrix_UB_33      0.0090099000
_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                1903
_reflns_number_total             2094
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (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    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.080
_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)+(0.0569P)²+0.0956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03571(17) 0.57216(13) 0.72726(8) 0.0277(2) Uani 1 1 d . . . . .
O2 O -0.24140(16) 0.42785(13) 0.83278(8) 0.0238(2) Uani 1 1 d . . . . .
O3 O 0.22331(14) 0.42140(11) 0.54856(7) 0.0180(2) Uani 1 1 d . . . . .
O4 O 0.12924(14) 0.14368(12) 0.55050(8) 0.0198(2) Uani 1 1 d . . . . .
N1 N -0.32887(17) 0.10055(14) 0.67909(9) 0.0176(2) Uani 1 1 d . . . . .
N2 N -0.47304(16) -0.03012(14) 0.72728(9) 0.0170(2) Uani 1 1 d . . . . .
N3 N -0.14361(16) 0.02752(13) 0.85034(8) 0.0149(2) Uani 1 1 d . . . . .
N4 N -0.08002(17) 0.43692(14) 0.75181(9) 0.0172(2) Uani 1 1 d . . . . .
N5 N 0.10971(16) 0.28656(13) 0.59488(8) 0.0144(2) Uani 1 1 d . . . . .
C1 C -0.17935(19) 0.12886(16) 0.74350(10) 0.0150(2) Uani 1 1 d . . . . .
C2 C -0.45951(18) -0.12609(16) 0.83504(10) 0.0145(2) Uani 1 1 d . . . . .
C3 C -0.28146(18) -0.10335(15) 0.89669(10) 0.0141(2) Uani 1 1 d . . . . .
C4 C -0.04094(19) 0.28752(16) 0.69448(10) 0.0153(2) Uani 1 1 d . . . . .
C5 C -0.63582(19) -0.25651(17) 0.88787(11) 0.0178(2) Uani 1 1 d . . . . .
H5A H -0.719706 -0.218122 0.958053 0.027 Uiso 1 1 calc R U . . .
H5B H -0.561131 -0.385498 0.908566 0.027 Uiso 1 1 calc R U . . .
H5C H -0.742248 -0.251420 0.831644 0.027 Uiso 1 1 calc R U . . .
C6 C -0.24293(19) -0.22652(16) 1.01223(10) 0.0179(2) Uani 1 1 d . . . . .
H6A H -0.389385 -0.238017 1.061873 0.027 Uiso 1 1 calc R U . . .
H6B H -0.141605 -0.170622 1.049458 0.027 Uiso 1 1 calc R U . . .
H6C H -0.172528 -0.351699 1.001151 0.027 Uiso 1 1 calc R U . . .
N6 N 0.37047(17) 0.76228(14) 0.56687(9) 0.0155(2) Uani 1 1 d . . . . .
H6D H 0.382(3) 0.851(2) 0.6074(15) 0.026(4) Uiso 1 1 d . . . . .
H6E H 0.277(3) 0.675(2) 0.6023(15) 0.027(4) Uiso 1 1 d . . . . .
H6F H 0.327(3) 0.823(3) 0.4931(17) 0.033(4) Uiso 1 1 d . . . . .
H6G H 0.510(4) 0.703(3) 0.5503(17) 0.036(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.2446(13) . ?
O2 N4 1.2507(13) . ?
O3 N5 1.2545(12) . ?
O4 N5 1.2559(13) . ?
N1 N2 1.3513(13) . ?
N1 C1 1.3241(15) . ?
N2 C2 1.3233(15) . ?
N3 C1 1.3497(15) . ?
N3 C3 1.3235(14) . ?
N4 C4 1.3870(15) . ?
N5 C4 1.3728(15) . ?
C1 C4 1.4829(15) . ?
C2 C3 1.4253(15) . ?
C2 C5 1.4944(15) . ?
C3 C6 1.4942(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N6 H6D 0.908(18) . ?
N6 H6E 0.900(18) . ?
N6 H6F 0.945(19) . ?
N6 H6G 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
C1 N1 N2 117.82(10) . . ?
C2 N2 N1 119.80(9) . . ?
C3 N3 C1 116.25(9) . . ?
O1 N4 O2 120.70(10) . . ?
O1 N4 C4 123.79(10) . . ?
O2 N4 C4 115.51(9) . . ?
O3 N5 O4 120.57(9) . . ?
O3 N5 C4 122.43(10) . . ?
O4 N5 C4 117.00(9) . . ?
N1 C1 N3 125.80(10) . . ?
N1 C1 C4 117.07(10) . . ?
N3 C1 C4 117.13(9) . . ?
N2 C2 C3 120.14(10) . . ?
N2 C2 C5 117.63(10) . . ?
C3 C2 C5 122.23(10) . . ?
N3 C3 C2 119.69(10) . . ?
N3 C3 C6 118.71(10) . . ?
C2 C3 C6 121.59(10) . . ?
N4 C4 C1 116.37(10) . . ?
N5 C4 N4 122.90(10) . . ?
N5 C4 C1 120.68(10) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H6D N6 H6E 115.9(16) . . ?
H6D N6 H6F 108.9(15) . . ?
H6D N6 H6G 109.0(16) . . ?
H6E N6 H6F 110.3(15) . . ?
H6E N6 H6G 108.2(16) . . ?
H6F N6 H6G 104.0(16) . . ?

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
N6 H6E O1 0.900(18) 2.000(18) 2.8312(13) 152.8(16) . yes
N6 H6E O3 0.900(18) 2.171(17) 2.8242(12) 128.9(15) . 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 N4 C4 N5 -9.02(18) . . . . ?
O1 N4 C4 C1 173.62(10) . . . . ?
O2 N4 C4 N5 171.62(10) . . . . ?
O2 N4 C4 C1 -5.74(15) . . . . ?
O3 N5 C4 N4 0.06(17) . . . . ?
O3 N5 C4 C1 177.30(9) . . . . ?
O4 N5 C4 N4 -179.53(10) . . . . ?
O4 N5 C4 C1 -2.28(15) . . . . ?
N1 N2 C2 C3 -5.26(16) . . . . ?
N1 N2 C2 C5 174.72(10) . . . . ?
N1 C1 C4 N4 113.45(12) . . . . ?
N1 C1 C4 N5 -63.97(14) . . . . ?
N2 N1 C1 N3 6.08(17) . . . . ?
N2 N1 C1 C4 -173.11(10) . . . . ?
N2 C2 C3 N3 6.72(16) . . . . ?
N2 C2 C3 C6 -172.13(10) . . . . ?
N3 C1 C4 N4 -65.81(14) . . . . ?
N3 C1 C4 N5 116.77(12) . . . . ?
C1 N1 N2 C2 -0.77(16) . . . . ?
C1 N3 C3 C2 -1.88(15) . . . . ?
C1 N3 C3 C6 177.00(10) . . . . ?
C3 N3 C1 N1 -4.58(17) . . . . ?
C3 N3 C1 C4 174.61(9) . . . . ?
C5 C2 C3 N3 -173.27(10) . . . . ?
C5 C2 C3 C6 7.88(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 A95
_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 1.119
_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_js1219b
_database_code_depnum_ccdc_archive 'CCDC 1975378'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H7 N11 O4'
_chemical_formula_sum            'C5 H7 N11 O4'
_chemical_formula_weight         285.22
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.0867(4)
_cell_length_b                   6.36110(10)
_cell_length_c                   13.7829(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.1240(10)
_cell_angle_gamma                90
_cell_volume                     2269.53(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4258
_cell_measurement_temperature    172.99
_cell_measurement_theta_max      70.06
_cell_measurement_theta_min      3.41
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.693
_exptl_absorpt_coefficient_mu    1.259
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0630 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.8599.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 4.00 0.1190
1.00 -5.00 0.00 0.0750
-2.00 5.00 0.00 0.1020
0.00 1.00 -5.00 0.0930
1.00 -5.00 1.00 0.0700
0.00 2.00 5.00 0.1190
1.00 0.00 0.00 0.0090
-1.00 0.00 0.00 0.0370

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.074
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  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  0.0292
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7818
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.052
_diffrn_reflns_theta_min         3.415
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1862
_reflns_number_total             2144
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.022
_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)+(0.0700P)²+1.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
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 was found 
by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3C,H3D)
;
_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 0.73163(4) 0.5326(2) 0.22450(8) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.81432(4) 0.52804(19) 0.24843(9) 0.0300(3) Uani 1 1 d . . . . .
O3 O 0.84922(5) 0.5705(2) 0.53798(9) 0.0338(3) Uani 1 1 d . . . . .
O4 O 0.85768(5) 0.7460(2) 0.40941(9) 0.0380(3) Uani 1 1 d . . . . .
N1 N 0.69508(5) 0.4782(2) 0.37480(10) 0.0229(3) Uani 1 1 d . . . . .
H1 H 0.6868(9) 0.500(3) 0.3103(18) 0.039(6) Uiso 1 1 d . . . . .
N2 N 0.65910(5) 0.4376(2) 0.42589(10) 0.0244(3) Uani 1 1 d . . . . .
N3 N 0.75351(6) 0.4976(2) 0.53184(10) 0.0245(3) Uani 1 1 d . . . . .
H3A H 0.7287(8) 0.478(3) 0.5538(15) 0.026(5) Uiso 1 1 d . . . . .
H3B H 0.7838(9) 0.502(3) 0.5706(17) 0.031(5) Uiso 1 1 d . . . . .
N4 N 0.60548(6) 0.6132(2) 0.21327(11) 0.0322(3) Uani 1 1 d . . . . .
N5 N 0.58183(6) 0.7686(2) 0.23096(11) 0.0334(3) Uani 1 1 d . . . . .
N6 N 0.56269(7) 0.9207(3) 0.24100(16) 0.0513(5) Uani 1 1 d . . . . .
N7 N 0.52935(6) 0.5051(3) 0.39801(13) 0.0391(4) Uani 1 1 d . . . . .
N8 N 0.53444(5) 0.6723(3) 0.44537(13) 0.0390(4) Uani 1 1 d . . . . .
N9 N 0.53340(8) 0.8284(3) 0.4822(2) 0.0699(6) Uani 1 1 d . . . . .
N10 N 0.77707(5) 0.53830(19) 0.28239(10) 0.0222(3) Uani 1 1 d . . . . .
N11 N 0.83364(5) 0.6231(2) 0.44721(10) 0.0262(3) Uani 1 1 d . . . . .
C1 C 0.61245(6) 0.4089(2) 0.37187(12) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.59283(6) 0.4141(2) 0.25732(12) 0.0276(4) Uani 1 1 d . . . . .
H2A H 0.608018 0.294834 0.229862 0.033 Uiso 1 1 calc R U . . .
H2B H 0.554863 0.395306 0.235840 0.033 Uiso 1 1 calc R U . . .
C3 C 0.57439(6) 0.3607(3) 0.42980(13) 0.0316(4) Uani 1 1 d . . . . .
H3C H 0.562438 0.213472 0.416895 0.038 Uiso 1 1 calc R U . . .
H3D H 0.591516 0.376705 0.503505 0.038 Uiso 1 1 calc R U . . .
C4 C 0.74408(6) 0.5073(2) 0.43251(11) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.78434(6) 0.5485(2) 0.38702(11) 0.0216(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N10 1.2550(17) . ?
O2 N10 1.2326(17) . ?
O3 N11 1.2427(18) . ?
O4 N11 1.2275(18) . ?
N1 H1 0.86(2) . ?
N1 N2 1.3843(18) . ?
N1 C4 1.344(2) . ?
N2 C1 1.277(2) . ?
N3 H3A 0.83(2) . ?
N3 H3B 0.84(2) . ?
N3 C4 1.318(2) . ?
N4 N5 1.241(2) . ?
N4 C2 1.487(2) . ?
N5 N6 1.126(2) . ?
N7 N8 1.234(2) . ?
N7 C3 1.486(2) . ?
N8 N9 1.119(3) . ?
N10 C5 1.3984(19) . ?
N11 C5 1.430(2) . ?
C1 C2 1.511(2) . ?
C1 C3 1.510(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 C5 1.433(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 H1 123.2(15) . . ?
C4 N1 H1 119.9(15) . . ?
C4 N1 N2 116.42(13) . . ?
C1 N2 N1 117.00(13) . . ?
H3A N3 H3B 121(2) . . ?
C4 N3 H3A 117.3(14) . . ?
C4 N3 H3B 121.1(15) . . ?
N5 N4 C2 113.82(13) . . ?
N6 N5 N4 173.00(18) . . ?
N8 N7 C3 114.99(15) . . ?
N9 N8 N7 172.1(2) . . ?
O1 N10 C5 118.09(12) . . ?
O2 N10 O1 121.09(12) . . ?
O2 N10 C5 120.78(13) . . ?
O3 N11 C5 118.50(13) . . ?
O4 N11 O3 122.23(14) . . ?
O4 N11 C5 119.12(13) . . ?
N2 C1 C2 126.13(14) . . ?
N2 C1 C3 115.68(15) . . ?
C3 C1 C2 118.18(14) . . ?
N4 C2 C1 113.13(13) . . ?
N4 C2 H2A 109.0 . . ?
N4 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N7 C3 C1 110.35(14) . . ?
N7 C3 H3C 109.6 . . ?
N7 C3 H3D 109.6 . . ?
C1 C3 H3C 109.6 . . ?
C1 C3 H3D 109.6 . . ?
H3C C3 H3D 108.1 . . ?
N1 C4 C5 120.82(14) . . ?
N3 C4 N1 117.64(14) . . ?
N3 C4 C5 121.54(15) . . ?
N10 C5 N11 115.95(13) . . ?
N10 C5 C4 123.26(14) . . ?
N11 C5 C4 120.53(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.86(2) 1.94(2) 2.5688(17) 129(2) . yes
N1 H1 N4 0.86(2) 2.33(2) 2.899(2) 123.9(18) . yes
N3 H3A O1 0.83(2) 2.33(2) 2.8926(17) 125.9(17) 6_566 yes
N3 H3B O2 0.84(2) 2.35(2) 2.9590(19) 129.9(18) 6_566 yes
N3 H3B O3 0.84(2) 2.00(2) 2.610(2) 128.9(19) . 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 N10 C5 N11 -160.17(13) . . . . ?
O1 N10 C5 C4 14.0(2) . . . . ?
O2 N10 C5 N11 22.23(19) . . . . ?
O2 N10 C5 C4 -163.61(14) . . . . ?
O3 N11 C5 N10 -155.64(13) . . . . ?
O3 N11 C5 C4 30.0(2) . . . . ?
O4 N11 C5 N10 28.6(2) . . . . ?
O4 N11 C5 C4 -145.76(15) . . . . ?
N1 N2 C1 C2 0.3(2) . . . . ?
N1 N2 C1 C3 178.81(13) . . . . ?
N1 C4 C5 N10 -7.3(2) . . . . ?
N1 C4 C5 N11 166.63(13) . . . . ?
N2 N1 C4 N3 -0.8(2) . . . . ?
N2 N1 C4 C5 179.48(12) . . . . ?
N2 C1 C2 N4 -55.3(2) . . . . ?
N2 C1 C3 N7 127.85(15) . . . . ?
N3 C4 C5 N10 173.06(13) . . . . ?
N3 C4 C5 N11 -13.0(2) . . . . ?
N5 N4 C2 C1 -68.86(18) . . . . ?
N8 N7 C3 C1 -88.02(19) . . . . ?
C2 C1 C3 N7 -53.50(19) . . . . ?
C3 C1 C2 N4 126.19(15) . . . . ?
C4 N1 N2 C1 -179.77(13) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AKC-154
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_js1221a
_database_code_depnum_ccdc_archive 'CCDC 2154058'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-12-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_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 N5 Na O4'
_chemical_formula_sum            'C4 H2 N5 Na O4'
_chemical_formula_weight         207.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H2N5NaO4
_chemical_oxdiff_usercomment     A96-Na
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'
Na Na 0.1353 0.1239 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.4451(2)
_cell_length_b                   7.51185(15)
_cell_length_c                   15.2435(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1425.06(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.1130
_cell_measurement_theta_min      3.6220
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.706
_exptl_absorpt_coefficient_mu    2.011
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0932
0 1 0 0.0932
0 0 1 0.0475
0 0 -1 0.0475
-1 0 0 0.0138
1 0 0 0.0138

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.028
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
-0.0000 -1.0000 0.0000 -0.1993 0.0043 -0.0477
0.0000 1.0000 -0.0000 0.1993 -0.0043 0.0477
0.0000 -0.0000 1.0000 -0.0215 0.0338 0.0928
-0.0000 0.0000 -1.0000 0.0215 -0.0338 -0.0928
-1.0000 0.0000 0.0000 0.0120 0.1167 -0.0397
1.0000 -0.0000 -0.0000 -0.0120 -0.1167 0.0397

_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6395
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.507
_diffrn_reflns_theta_min         4.587
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    108.00 173.00   0.50    1.08    --  113.25  31.00  22.00  130
  2  ω    138.00 174.00   0.50    1.08    --  113.25  61.00  30.00   72
  3  ω    135.00 170.00   0.50    1.08    --  113.25  45.00 -60.00   70
  4  ω    108.00 178.00   0.50    1.08    --  113.25 107.00-132.00  140
  5  ω    129.00 161.00   0.50    1.08    --  113.25  77.00-150.00   64
  6  ω    -23.00  26.00   0.50    0.27    --  -48.10  19.00 150.00   98
  7  ω    -70.00 -42.00   0.50    0.27    --  -48.10 125.00  30.00   56
  8  ω    -82.00 -32.00   0.50    0.27    --  -48.10 125.00-120.00  100
  9  ω    -58.00 -32.00   0.50    1.08    --  -91.75 107.00-132.00   52
 10  ω    -37.00  21.00   0.50    0.27    --  -48.10  31.00  22.00  116
 11  ω   -163.00-138.00   0.50    1.08    --  -91.75 -77.00-120.00   50
 12  ω   -159.00-134.00   0.50    1.08    --  -91.75 -77.00   0.00   50
 13  ω     42.00  70.00   0.50    1.08    --  113.25 -61.00-180.00   56
 14  ω     42.00  67.00   0.50    1.08    --  113.25 -61.00  90.00   50
 15  ω     42.00  67.00   0.50    1.08    --  113.25 -61.00 120.00   50
 16  ω     47.00  95.00   0.50    1.08    --  113.25 -99.00  30.00   96
 17  ω     79.00 105.00   0.50    1.08    --  113.25-125.00-180.00   52
 18  ω     46.00  72.00   0.50    1.08    --  113.25-125.00-180.00   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      -0.0119882000
_diffrn_orient_matrix_UB_12      0.1993361000
_diffrn_orient_matrix_UB_13      -0.0215108000
_diffrn_orient_matrix_UB_21      -0.1166647000
_diffrn_orient_matrix_UB_22      -0.0043251000
_diffrn_orient_matrix_UB_23      0.0338014000
_diffrn_orient_matrix_UB_31      0.0397036000
_diffrn_orient_matrix_UB_32      0.0477341000
_diffrn_orient_matrix_UB_33      0.0927923000
_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                1471
_reflns_number_total             1639
_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    '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         0.287
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.5436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.65991(6) 0.750000 0.65259(4) 0.01587(18) Uani 1 2 d S T P . .
Na2 Na 1.19480(6) 0.750000 0.33437(4) 0.01567(18) Uani 1 2 d S T P . .
O1 O 0.47410(8) 0.54735(12) 0.62788(6) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.62994(7) 0.42431(12) 0.64997(6) 0.0196(2) Uani 1 1 d . . . . .
O3 O 0.82342(7) 0.57415(12) 0.68808(6) 0.0160(2) Uani 1 1 d . . . . .
O4 O 0.97662(7) 0.45282(12) 0.65497(6) 0.0195(2) Uani 1 1 d . . . . .
N1 N 0.33855(13) 0.250000 0.51883(10) 0.0188(3) Uani 1 2 d S T P . .
N2 N 0.23328(13) 0.250000 0.49671(10) 0.0208(3) Uani 1 2 d S T P . .
N3 N 0.29363(12) 0.250000 0.67097(9) 0.0150(3) Uani 1 2 d S T P . .
N4 N 0.53143(8) 0.41058(14) 0.63458(7) 0.0152(2) Uani 1 1 d . . . . .
N5 N 1.08726(12) 0.750000 0.53264(10) 0.0183(3) Uani 1 2 d S T P . .
N6 N 1.18558(12) 0.750000 0.49553(10) 0.0184(3) Uani 1 2 d S T P . .
N7 N 1.16380(12) 0.750000 0.67656(9) 0.0151(3) Uani 1 2 d S T P . .
N8 N 0.91988(8) 0.58911(14) 0.66660(6) 0.0138(2) Uani 1 1 d . . . . .
C1 C 0.36383(14) 0.250000 0.60369(11) 0.0141(3) Uani 1 2 d S T P . .
C2 C 0.16056(15) 0.250000 0.55964(12) 0.0190(4) Uani 1 2 d S T P . .
H2 H 0.088(2) 0.250000 0.5441(16) 0.026(6) Uiso 1 2 d S . P . .
C3 C 0.19097(15) 0.250000 0.64804(12) 0.0177(4) Uani 1 2 d S T P . .
H3 H 0.138(2) 0.250000 0.6954(16) 0.027(6) Uiso 1 2 d S . P . .
C4 C 0.48002(14) 0.250000 0.62418(12) 0.0154(4) Uani 1 2 d S T P . .
C5 C 1.08128(14) 0.750000 0.61989(11) 0.0135(3) Uani 1 2 d S T P . .
C6 C 1.27051(15) 0.750000 0.54770(12) 0.0181(4) Uani 1 2 d S T P . .
H6 H 1.3402(19) 0.750000 0.5208(14) 0.017(5) Uiso 1 2 d S . P . .
C7 C 1.26015(15) 0.750000 0.63905(11) 0.0164(4) Uani 1 2 d S T P . .
H7 H 1.3211(19) 0.750000 0.6744(15) 0.018(6) Uiso 1 2 d S . P . .
C8 C 0.97041(14) 0.750000 0.65484(11) 0.0133(3) Uani 1 2 d S T P . .


_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
Na1 Na2 4.1732(4) 5_776 ?
Na1 O1 2.7940(11) 7_575 ?
Na1 O1 2.7940(11) . ?
Na1 O2 2.4751(9) . ?
Na1 O2 2.4751(9) 7_575 ?
Na1 O3 2.4856(10) 7_575 ?
Na1 O3 2.4856(10) . ?
Na1 N1 2.6132(16) 5_666 ?
Na1 N2 2.6358(17) 5_666 ?
Na1 N4 3.0220(11) 7_575 ?
Na1 N4 3.0220(11) . ?
Na1 N7 2.6048(16) 6_557 ?
Na2 O2 2.5550(11) 5_766 ?
Na2 O2 2.5550(11) 3_756 ?
Na2 O3 2.4693(9) 3_756 ?
Na2 O3 2.4693(9) 5_766 ?
Na2 O4 2.6267(11) 5_766 ?
Na2 O4 2.6267(11) 3_756 ?
Na2 N3 2.4949(15) 2_664 ?
Na2 N6 2.4593(16) . ?
Na2 N8 2.9199(11) 5_766 ?
Na2 N8 2.9199(11) 3_756 ?
O1 N4 1.2550(13) . ?
O2 N4 1.2525(14) . ?
O3 N8 1.2494(14) . ?
O4 N8 1.2563(13) . ?
N1 N2 1.353(2) . ?
N1 C1 1.331(2) . ?
N2 C2 1.319(3) . ?
N3 C1 1.347(2) . ?
N3 C3 1.325(2) . ?
N4 C4 1.3747(13) . ?
N5 N6 1.348(2) . ?
N5 C5 1.332(2) . ?
N6 C6 1.323(2) . ?
N7 C5 1.342(2) . ?
N7 C7 1.328(2) . ?
N8 C8 1.3742(13) . ?
C1 C4 1.479(2) . ?
C2 H2 0.93(3) . ?
C2 C3 1.400(3) . ?
C3 H3 0.98(3) . ?
C5 C8 1.479(2) . ?
C6 H6 0.96(2) . ?
C6 C7 1.398(2) . ?
C7 H7 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na1 Na2 82.80(2) 7_575 5_776 ?
O1 Na1 Na2 148.80(3) . 5_776 ?
O1 Na1 O1 66.03(4) . 7_575 ?
O1 Na1 N4 24.52(3) . . ?
O1 Na1 N4 90.55(3) . 7_575 ?
O1 Na1 N4 90.55(3) 7_575 . ?
O1 Na1 N4 24.52(3) 7_575 7_575 ?
O2 Na1 Na2 34.56(2) 7_575 5_776 ?
O2 Na1 Na2 162.87(3) . 5_776 ?
O2 Na1 O1 114.31(4) 7_575 . ?
O2 Na1 O1 48.28(3) . . ?
O2 Na1 O1 48.29(3) 7_575 7_575 ?
O2 Na1 O1 114.31(4) . 7_575 ?
O2 Na1 O2 162.57(5) . 7_575 ?
O2 Na1 O3 130.70(4) . 7_575 ?
O2 Na1 O3 130.70(4) 7_575 . ?
O2 Na1 O3 66.52(3) 7_575 7_575 ?
O2 Na1 O3 66.52(3) . . ?
O2 Na1 N1 89.14(3) . 5_666 ?
O2 Na1 N1 89.14(3) 7_575 5_666 ?
O2 Na1 N2 93.56(3) 7_575 5_666 ?
O2 Na1 N2 93.56(3) . 5_666 ?
O2 Na1 N4 23.78(3) 7_575 7_575 ?
O2 Na1 N4 23.78(3) . . ?
O2 Na1 N4 138.83(4) 7_575 . ?
O2 Na1 N4 138.83(4) . 7_575 ?
O2 Na1 N7 91.09(3) . 6_557 ?
O2 Na1 N7 91.09(3) 7_575 6_557 ?
O3 Na1 Na2 96.50(3) . 5_776 ?
O3 Na1 Na2 32.50(2) 7_575 5_776 ?
O3 Na1 O1 175.17(4) 7_575 . ?
O3 Na1 O1 114.67(3) 7_575 7_575 ?
O3 Na1 O1 175.16(4) . 7_575 ?
O3 Na1 O1 114.67(3) . . ?
O3 Na1 O3 64.21(4) 7_575 . ?
O3 Na1 N1 102.21(4) 7_575 5_666 ?
O3 Na1 N1 102.21(4) . 5_666 ?
O3 Na1 N2 77.00(4) 7_575 5_666 ?
O3 Na1 N2 77.00(4) . 5_666 ?
O3 Na1 N4 90.26(3) 7_575 7_575 ?
O3 Na1 N4 154.33(3) 7_575 . ?
O3 Na1 N4 154.33(3) . 7_575 ?
O3 Na1 N4 90.26(3) . . ?
O3 Na1 N7 76.54(4) . 6_557 ?
O3 Na1 N7 76.54(4) 7_575 6_557 ?
N1 Na1 Na2 92.55(2) 5_666 5_776 ?
N1 Na1 O1 82.60(4) 5_666 . ?
N1 Na1 O1 82.61(4) 5_666 7_575 ?
N1 Na1 N2 29.87(5) 5_666 5_666 ?
N1 Na1 N4 85.01(3) 5_666 . ?
N1 Na1 N4 85.01(3) 5_666 7_575 ?
N2 Na1 Na2 79.78(2) 5_666 5_776 ?
N2 Na1 O1 107.52(4) 5_666 7_575 ?
N2 Na1 O1 107.52(4) 5_666 . ?
N2 Na1 N4 100.86(3) 5_666 7_575 ?
N2 Na1 N4 100.86(3) 5_666 . ?
N4 Na1 Na2 173.16(3) . 5_776 ?
N4 Na1 Na2 58.28(2) 7_575 5_776 ?
N4 Na1 N4 115.07(5) 7_575 . ?
N7 Na1 Na2 86.81(2) 6_557 5_776 ?
N7 Na1 O1 98.64(4) 6_557 7_575 ?
N7 Na1 O1 98.64(4) 6_557 . ?
N7 Na1 N1 178.51(6) 6_557 5_666 ?
N7 Na1 N2 148.64(6) 6_557 5_666 ?
N7 Na1 N4 95.78(3) 6_557 7_575 ?
N7 Na1 N4 95.78(3) 6_557 . ?
Na1 Na2 Na1 128.32(2) 5_776 5_766 ?
O2 Na2 Na1 33.33(2) 3_756 5_776 ?
O2 Na2 Na1 94.99(3) 5_766 5_776 ?
O2 Na2 Na1 94.99(3) 3_756 5_766 ?
O2 Na2 Na1 33.33(2) 5_766 5_766 ?
O2 Na2 O2 61.66(4) 3_756 5_766 ?
O2 Na2 O4 112.97(3) 3_756 3_756 ?
O2 Na2 O4 170.00(4) 5_766 3_756 ?
O2 Na2 O4 170.00(4) 3_756 5_766 ?
O2 Na2 O4 112.97(3) 5_766 5_766 ?
O2 Na2 N8 88.32(3) 5_766 5_766 ?
O2 Na2 N8 88.32(3) 3_756 3_756 ?
O2 Na2 N8 149.86(3) 3_756 5_766 ?
O2 Na2 N8 149.86(3) 5_766 3_756 ?
O3 Na2 Na1 32.74(2) 5_766 5_766 ?
O3 Na2 Na1 32.74(2) 3_756 5_776 ?
O3 Na2 Na1 159.05(3) 5_766 5_776 ?
O3 Na2 Na1 159.05(3) 3_756 5_766 ?
O3 Na2 O2 126.63(4) 5_766 3_756 ?
O3 Na2 O2 65.54(3) 3_756 3_756 ?
O3 Na2 O2 65.54(3) 5_766 5_766 ?
O3 Na2 O2 126.63(4) 3_756 5_766 ?
O3 Na2 O3 160.87(5) 5_766 3_756 ?
O3 Na2 O4 120.40(4) 3_756 5_766 ?
O3 Na2 O4 50.36(3) 3_756 3_756 ?
O3 Na2 O4 120.40(4) 5_766 3_756 ?
O3 Na2 O4 50.36(3) 5_766 5_766 ?
O3 Na2 N3 82.36(3) 3_756 2_664 ?
O3 Na2 N3 82.36(3) 5_766 2_664 ?
O3 Na2 N8 25.06(3) 5_766 5_766 ?
O3 Na2 N8 144.56(4) 3_756 5_766 ?
O3 Na2 N8 25.06(3) 3_756 3_756 ?
O3 Na2 N8 144.56(4) 5_766 3_756 ?
O4 Na2 Na1 80.03(2) 5_766 5_766 ?
O4 Na2 Na1 150.58(3) 5_766 5_776 ?
O4 Na2 Na1 150.58(3) 3_756 5_766 ?
O4 Na2 Na1 80.03(2) 3_756 5_776 ?
O4 Na2 O4 70.91(4) 5_766 3_756 ?
O4 Na2 N8 96.28(4) 3_756 5_766 ?
O4 Na2 N8 25.48(3) 5_766 5_766 ?
O4 Na2 N8 25.48(3) 3_756 3_756 ?
O4 Na2 N8 96.28(4) 5_766 3_756 ?
N3 Na2 Na1 91.29(2) 2_664 5_766 ?
N3 Na2 Na1 91.29(2) 2_664 5_776 ?
N3 Na2 O2 92.52(4) 2_664 5_766 ?
N3 Na2 O2 92.52(4) 2_664 3_756 ?
N3 Na2 O4 96.24(4) 2_664 3_756 ?
N3 Na2 O4 96.24(4) 2_664 5_766 ?
N3 Na2 N8 91.33(3) 2_664 3_756 ?
N3 Na2 N8 91.33(3) 2_664 5_766 ?
N6 Na2 Na1 88.43(2) . 5_776 ?
N6 Na2 Na1 88.43(2) . 5_766 ?
N6 Na2 O2 86.93(4) . 3_756 ?
N6 Na2 O2 86.93(4) . 5_766 ?
N6 Na2 O3 97.71(3) . 5_766 ?
N6 Na2 O3 97.71(3) . 3_756 ?
N6 Na2 O4 84.28(4) . 5_766 ?
N6 Na2 O4 84.28(4) . 3_756 ?
N6 Na2 N3 179.37(6) . 2_664 ?
N6 Na2 N8 88.98(3) . 3_756 ?
N6 Na2 N8 88.98(3) . 5_766 ?
N8 Na2 Na1 175.69(3) 5_766 5_776 ?
N8 Na2 Na1 55.03(2) 3_756 5_776 ?
N8 Na2 Na1 55.03(2) 5_766 5_766 ?
N8 Na2 Na1 175.69(3) 3_756 5_766 ?
N8 Na2 N8 121.48(5) 5_766 3_756 ?
N4 O1 Na1 87.96(7) . . ?
Na1 O2 Na2 112.11(4) . 5_766 ?
N4 O2 Na1 103.41(7) . . ?
N4 O2 Na2 144.18(8) . 5_766 ?
Na2 O3 Na1 114.75(4) 5_766 . ?
N8 O3 Na1 132.99(7) . . ?
N8 O3 Na2 98.08(7) . 5_766 ?
N8 O4 Na2 90.42(7) . 5_766 ?
N2 N1 Na1 75.99(9) . 5_666 ?
C1 N1 Na1 165.91(13) . 5_666 ?
C1 N1 N2 118.11(15) . . ?
N1 N2 Na1 74.15(9) . 5_666 ?
C2 N2 Na1 166.96(13) . 5_666 ?
C2 N2 N1 118.90(15) . . ?
C1 N3 Na2 136.27(12) . 2_665 ?
C3 N3 Na2 108.61(11) . 2_665 ?
C3 N3 C1 115.12(15) . . ?
O1 N4 Na1 67.51(6) . . ?
O1 N4 C4 116.38(11) . . ?
O2 N4 Na1 52.82(6) . . ?
O2 N4 O1 120.29(10) . . ?
O2 N4 C4 123.33(11) . . ?
C4 N4 Na1 175.64(9) . . ?
C5 N5 N6 118.02(15) . . ?
N5 N6 Na2 117.49(11) . . ?
C6 N6 Na2 124.29(12) . . ?
C6 N6 N5 118.22(15) . . ?
C5 N7 Na1 129.00(12) . 6_657 ?
C7 N7 Na1 116.56(11) . 6_657 ?
C7 N7 C5 114.44(15) . . ?
O3 N8 Na2 56.85(6) . 5_766 ?
O3 N8 O4 120.26(10) . . ?
O3 N8 C8 123.57(11) . . ?
O4 N8 Na2 64.10(6) . 5_766 ?
O4 N8 C8 116.17(11) . . ?
C8 N8 Na2 172.01(9) . 5_766 ?
N1 C1 N3 125.90(16) . . ?
N1 C1 C4 115.86(15) . . ?
N3 C1 C4 118.24(15) . . ?
N2 C2 H2 118.5(15) . . ?
N2 C2 C3 120.98(17) . . ?
C3 C2 H2 120.5(15) . . ?
N3 C3 C2 120.99(17) . . ?
N3 C3 H3 116.9(15) . . ?
C2 C3 H3 122.1(15) . . ?
N4 C4 N4 122.69(16) . 7_565 ?
N4 C4 C1 118.64(8) . . ?
N4 C4 C1 118.64(8) 7_565 . ?
N5 C5 N7 126.86(16) . . ?
N5 C5 C8 114.31(15) . . ?
N7 C5 C8 118.83(15) . . ?
N6 C6 H6 117.7(13) . . ?
N6 C6 C7 121.67(17) . . ?
C7 C6 H6 120.6(13) . . ?
N7 C7 C6 120.79(16) . . ?
N7 C7 H7 119.1(14) . . ?
C6 C7 H7 120.1(14) . . ?
N8 C8 N8 123.16(15) . 7_575 ?
N8 C8 C5 118.29(8) 7_575 . ?
N8 C8 C5 118.29(8) . . ?

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
Na1 O1 N4 O2 2.17(11) . . . . ?
Na1 O1 N4 C4 -177.84(11) . . . . ?
Na1 O2 N4 O1 -2.52(13) . . . . ?
Na1 O2 N4 C4 177.49(12) . . . . ?
Na1 O3 N8 Na2 -135.27(10) . . . 5_766 ?
Na1 O3 N8 O4 -145.23(9) . . . . ?
Na1 O3 N8 C8 35.17(17) . . . . ?
Na1 N1 N2 C2 180.000(0) 5_666 . . . ?
Na1 N1 C1 N3 180.000(1) 5_666 . . . ?
Na1 N1 C1 C4 0.000(1) 5_666 . . . ?
Na1 N2 C2 C3 180.000(1) 5_666 . . . ?
Na1 N7 C5 N5 180.000(0) 6_657 . . . ?
Na1 N7 C5 C8 0.000(0) 6_657 . . . ?
Na1 N7 C7 C6 180.000(0) 6_657 . . . ?
Na2 O2 N4 Na1 -172.53(16) 5_766 . . . ?
Na2 O2 N4 O1 -175.05(9) 5_766 . . . ?
Na2 O2 N4 C4 5.0(2) 5_766 . . . ?
Na2 O3 N8 O4 -9.95(11) 5_766 . . . ?
Na2 O3 N8 C8 170.45(11) 5_766 . . . ?
Na2 O4 N8 O3 9.26(10) 5_766 . . . ?
Na2 O4 N8 C8 -171.11(10) 5_766 . . . ?
Na2 N3 C1 N1 180.000(0) 2_665 . . . ?
Na2 N3 C1 C4 0.000(0) 2_665 . . . ?
Na2 N3 C3 C2 180.000(0) 2_665 . . . ?
Na2 N6 C6 C7 180.000(0) . . . . ?
O1 N4 C4 N4 -176.30(11) . . . 7_565 ?
O1 N4 C4 C1 1.7(2) . . . . ?
O2 N4 C4 N4 3.7(3) . . . 7_565 ?
O2 N4 C4 C1 -178.29(13) . . . . ?
O3 N8 C8 N8 0.8(2) . . . 7_575 ?
O3 N8 C8 C5 -173.31(12) . . . . ?
O4 N8 C8 N8 -178.82(11) . . . 7_575 ?
O4 N8 C8 C5 7.07(19) . . . . ?
N1 N2 C2 C3 0.000(0) . . . . ?
N1 C1 C4 N4 90.95(14) . . . . ?
N1 C1 C4 N4 -90.95(14) . . . 7_565 ?
N2 N1 C1 N3 0.000(0) . . . . ?
N2 N1 C1 C4 180.000(0) . . . . ?
N2 C2 C3 N3 0.000(0) . . . . ?
N3 C1 C4 N4 -89.05(14) . . . . ?
N3 C1 C4 N4 89.05(14) . . . 7_565 ?
N5 N6 C6 C7 0.000(0) . . . . ?
N5 C5 C8 N8 -87.20(13) . . . 7_575 ?
N5 C5 C8 N8 87.20(13) . . . . ?
N6 N5 C5 N7 0.000(0) . . . . ?
N6 N5 C5 C8 180.000(0) . . . . ?
N6 C6 C7 N7 0.000(0) . . . . ?
N7 C5 C8 N8 92.80(13) . . . 7_575 ?
N7 C5 C8 N8 -92.80(13) . . . . ?
C1 N1 N2 Na1 180.000(0) . . . 5_666 ?
C1 N1 N2 C2 0.000(0) . . . . ?
C1 N3 C3 C2 0.000(0) . . . . ?
C3 N3 C1 N1 0.000(0) . . . . ?
C3 N3 C1 C4 180.000(0) . . . . ?
C5 N5 N6 Na2 180.000(0) . . . . ?
C5 N5 N6 C6 0.000(0) . . . . ?
C5 N7 C7 C6 0.000(0) . . . . ?
C7 N7 C5 N5 0.000(0) . . . . ?
C7 N7 C5 C8 180.000(0) . . . . ?

_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 A96-Na
_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 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.847
####################################################################### 
# 
# 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_js721cn
_database_code_depnum_ccdc_archive 'CCDC 2154056'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 K N5 O4'
_chemical_formula_sum            'C6 H6 K N5 O4'
_chemical_formula_weight         251.26
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H6KN5O4
_chemical_oxdiff_usercomment     'A70 Needles'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.95992(19)
_cell_length_b                   12.8763(3)
_cell_length_c                   18.8416(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1931.16(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5852
_cell_measurement_temperature    99.98(16)
_cell_measurement_theta_max      78.1170
_cell_measurement_theta_min      4.6720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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    1.728
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0179
1 0 0 0.1107
-1 0 0 0.1245
0 1 0 0.0189
0 -1 0 0.0174
0 0 1 0.0110
0 0 -1 0.0127

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.024
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
0.0008 1.0008 0.9986 -0.0225 0.0455 0.1358
1.0005 0.0008 -0.0001 -0.0837 0.1610 -0.0678
-1.0005 -0.0008 0.0001 0.0837 -0.1610 0.0678
0.0008 1.0008 -0.0002 -0.0753 0.0002 0.0931
-0.0008 -1.0008 0.0002 0.0753 -0.0002 -0.0931
-0.0000 0.0000 0.9987 0.0528 0.0454 0.0427
0.0000 -0.0000 -0.9987 -0.0528 -0.0454 -0.0427

_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  0.0465
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9448
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.359
_diffrn_reflns_theta_min         4.159
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(16)
_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 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  61.00   0.50    0.48    --   47.36  51.00  72.00   54
  2  ω    127.00 174.00   0.50    1.92    --  113.25  61.00 150.00   94
  3  ω    131.00 172.00   0.50    1.92    --  113.25  61.00 120.00   82
  4  ω    124.00 163.00   0.50    1.92    --  113.25  51.00  72.00   78
  5  ω     92.00 118.00   0.50    0.48    --   47.36  51.00  72.00   52
  6  ω    128.00 173.00   0.50    1.92    --  113.25  61.00 -30.00   90
  7  ω    134.00 160.00   0.50    1.92    --  113.25  80.00 -78.00   52
  8  ω    122.00 176.00   0.50    1.92    --  113.25  45.00-150.00  108
  9  ω     -6.00  28.00   0.50    0.48    --  -47.36  19.00 -90.00   68
 10  ω    -69.00 -21.00   0.50    0.48    --  -47.36  80.00 -78.00   96
 11  ω   -162.00-126.00   0.50    1.92    --  -91.75 -77.00-180.00   72
 12  ω    -73.00 -48.00   0.50    1.92    --  -91.75  96.00 171.00   50
 13  ω    -61.00   9.00   0.50    0.48    --  -47.36  57.00 150.00  140
 14  ω     42.00  70.00   0.50    1.92    --  113.25 -61.00   0.00   56
 15  ω     54.00 101.00   0.50    1.92    --  113.25 -77.00 120.00   94
 16  ω     43.00  68.00   0.50    1.92    --  113.25 -61.00 -90.00   50
 17  ω     42.00  69.00   0.50    1.92    --  113.25 -61.00-120.00   54
 18  ω     46.00 104.00   0.50    1.92    --  113.25 -94.00-150.00  116
 19  ω     36.00  70.00   0.50    0.48    --   47.36-125.00 -90.00   68
 20  ω     57.00 101.00   0.50    1.92    --  113.25 -96.00  62.00   88
;
_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      -0.0835459000
_diffrn_orient_matrix_UB_12      -0.0751628000
_diffrn_orient_matrix_UB_13      0.0528624000
_diffrn_orient_matrix_UB_21      0.1609172000
_diffrn_orient_matrix_UB_22      0.0000397000
_diffrn_orient_matrix_UB_23      0.0454183000
_diffrn_orient_matrix_UB_31      -0.0677997000
_diffrn_orient_matrix_UB_32      0.0930620000
_diffrn_orient_matrix_UB_33      0.0427522000
_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         0.642
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                3633
_reflns_number_total             3872
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.375(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.134
_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)+(0.0603P)²+0.7510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          'Refined as a 2-component inversion twin.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.625(15)
 0.375(15)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
3.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_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 0.81967(11) 0.67579(6) 0.51945(5) 0.0204(2) Uani 1 1 d . . . . .
K2 K 0.52494(11) 0.16596(6) 0.51296(5) 0.0213(2) Uani 1 1 d . . . . .
O1 O 0.9714(4) 0.8136(2) 0.43101(16) 0.0236(6) Uani 1 1 d . . . . .
O2 O 1.1004(4) 0.9563(2) 0.40353(16) 0.0231(6) Uani 1 1 d . . . . .
O3 O 0.6657(4) 0.8546(2) 0.47884(17) 0.0254(6) Uani 1 1 d . . . . .
O4 O 0.5419(4) 0.9831(2) 0.42456(17) 0.0238(6) Uani 1 1 d . . . . .
O5 O 0.7909(4) 0.4900(2) 0.43876(17) 0.0236(6) Uani 1 1 d . . . . .
O6 O 0.6710(4) 0.3559(2) 0.48856(17) 0.0228(6) Uani 1 1 d . . . . .
O7 O 0.3638(4) 0.3179(2) 0.44166(17) 0.0255(6) Uani 1 1 d . . . . .
O8 O 0.2499(4) 0.4458(2) 0.38375(18) 0.0281(7) Uani 1 1 d . . . . .
N1 N 0.8837(5) 1.0485(3) 0.29720(18) 0.0193(7) Uani 1 1 d . . . . .
N2 N 0.7798(5) 1.1477(3) 0.3950(2) 0.0259(8) Uani 1 1 d . . . . .
N3 N 0.7962(5) 1.2358(3) 0.3571(2) 0.0270(8) Uani 1 1 d . . . . .
N4 N 0.9682(5) 0.9076(2) 0.41498(18) 0.0186(7) Uani 1 1 d . . . . .
N5 N 0.6726(5) 0.9303(2) 0.4379(2) 0.0205(7) Uani 1 1 d . . . . .
N6 N 0.5921(5) 0.5487(3) 0.30255(19) 0.0202(7) Uani 1 1 d . . . . .
N7 N 0.4756(5) 0.6441(3) 0.3991(2) 0.0263(8) Uani 1 1 d . . . . .
N8 N 0.4842(5) 0.7327(3) 0.3610(2) 0.0272(8) Uani 1 1 d . . . . .
N9 N 0.6638(5) 0.4322(2) 0.4484(2) 0.0204(7) Uani 1 1 d . . . . .
N10 N 0.3748(5) 0.4055(3) 0.4135(2) 0.0208(7) Uani 1 1 d . . . . .
C1 C 0.8190(5) 0.9632(3) 0.4072(2) 0.0197(8) Uani 1 1 d . . . . .
C2 C 0.8268(5) 1.0598(3) 0.3645(2) 0.0203(8) Uani 1 1 d . . . . .
C3 C 0.9005(5) 1.1348(3) 0.2598(2) 0.0199(8) Uani 1 1 d . . . . .
C4 C 0.8568(6) 1.2318(3) 0.2916(2) 0.0225(8) Uani 1 1 d . . . . .
C5 C 0.9633(6) 1.1275(3) 0.1858(2) 0.0245(9) Uani 1 1 d . . . . .
H5A H 1.010236 1.058161 0.177671 0.037 Uiso 1 1 calc R U . . .
H5B H 1.050780 1.179890 0.178191 0.037 Uiso 1 1 calc R U . . .
H5C H 0.870374 1.139638 0.152721 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8802(7) 1.3338(3) 0.2540(2) 0.0285(9) Uani 1 1 d . . . . .
H6A H 0.829865 1.389606 0.282209 0.043 Uiso 1 1 calc R U . . .
H6B H 0.825516 1.330823 0.207396 0.043 Uiso 1 1 calc R U . . .
H6C H 1.000424 1.347384 0.247719 0.043 Uiso 1 1 calc R U . . .
C7 C 0.5218(5) 0.4621(3) 0.4122(2) 0.0198(8) Uani 1 1 d . . . . .
C8 C 0.5293(5) 0.5579(3) 0.3686(2) 0.0191(8) Uani 1 1 d . . . . .
C9 C 0.6024(5) 0.6357(3) 0.2651(2) 0.0198(8) Uani 1 1 d . . . . .
C10 C 0.5479(6) 0.7311(3) 0.2963(2) 0.0213(8) Uani 1 1 d . . . . .
C11 C 0.5596(6) 0.8326(3) 0.2581(2) 0.0281(9) Uani 1 1 d . . . . .
H11A H 0.514140 0.887962 0.288168 0.042 Uiso 1 1 calc R U . . .
H11B H 0.494964 0.828902 0.213875 0.042 Uiso 1 1 calc R U . . .
H11C H 0.677529 0.847590 0.247079 0.042 Uiso 1 1 calc R U . . .
C31 C 0.6692(7) 0.6305(3) 0.1915(2) 0.0281(9) Uani 1 1 d . . . . .
H31A H 0.721539 0.562576 0.183637 0.042 Uiso 1 1 calc R U . . .
H31B H 0.752992 0.685321 0.184687 0.042 Uiso 1 1 calc R U . . .
H31C H 0.576963 0.640131 0.157667 0.042 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 K1 4.4754(7) 4_466 ?
K1 O1 2.718(3) . ?
K1 O1 2.929(3) 4_466 ?
K1 O2 2.836(3) 4_466 ?
K1 O3 2.718(3) . ?
K1 O3 2.782(3) 4_566 ?
K1 O4 2.903(3) 4_566 ?
K1 O5 2.844(3) . ?
K1 N4 3.241(4) 4_466 ?
K1 N5 3.225(4) 4_566 ?
K1 N7 3.046(4) 4_566 ?
K1 N8 2.859(4) 4_566 ?
K2 K2 4.5565(7) 4_456 ?
K2 O4 2.887(3) 1_545 ?
K2 O5 2.886(3) 4_456 ?
K2 O6 2.832(3) 4_456 ?
K2 O6 2.747(3) . ?
K2 O7 2.698(3) . ?
K2 O7 2.838(3) 4_556 ?
K2 O8 3.011(3) 4_556 ?
K2 N2 3.019(4) 1_545 ?
K2 N3 3.303(4) 4_466 ?
K2 N9 3.224(4) 4_456 ?
K2 N10 3.244(4) 4_556 ?
O1 N4 1.247(4) . ?
O2 N4 1.244(5) . ?
O3 N5 1.244(4) . ?
O4 N5 1.268(5) . ?
O5 N9 1.269(5) . ?
O6 N9 1.242(4) . ?
O7 N10 1.249(5) . ?
O8 N10 1.254(5) . ?
N1 C2 1.355(5) . ?
N1 C3 1.324(5) . ?
N2 N3 1.346(5) . ?
N2 C2 1.323(5) . ?
N3 C4 1.326(6) . ?
N4 C1 1.395(5) . ?
N5 C1 1.369(5) . ?
N6 C8 1.347(6) . ?
N6 C9 1.326(5) . ?
N7 N8 1.349(5) . ?
N7 C8 1.321(5) . ?
N8 C10 1.321(6) . ?
N9 C7 1.374(6) . ?
N10 C7 1.379(5) . ?
C1 C2 1.482(5) . ?
C3 C4 1.429(6) . ?
C3 C5 1.483(6) . ?
C4 C6 1.504(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.483(5) . ?
C9 C10 1.429(5) . ?
C9 C31 1.486(6) . ?
C10 C11 1.496(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 K1 90.91(7) . 4_466 ?
O1 K1 K1 35.95(6) 4_466 4_466 ?
O1 K1 O1 125.85(8) . 4_466 ?
O1 K1 O2 168.17(10) . 4_466 ?
O1 K1 O3 70.06(9) . 4_566 ?
O1 K1 O3 58.30(9) . . ?
O1 K1 O4 114.36(9) . 4_566 ?
O1 K1 O5 104.92(9) . . ?
O1 K1 N4 146.46(9) . 4_466 ?
O1 K1 N4 22.59(8) 4_466 4_466 ?
O1 K1 N5 139.89(9) 4_466 4_566 ?
O1 K1 N5 92.43(9) . 4_566 ?
O1 K1 N7 68.33(10) . 4_566 ?
O1 K1 N7 100.94(10) 4_466 4_566 ?
O1 K1 N8 90.60(11) . 4_566 ?
O2 K1 K1 78.03(6) 4_466 4_466 ?
O2 K1 O1 44.13(8) 4_466 4_466 ?
O2 K1 O4 76.49(9) 4_466 4_566 ?
O2 K1 O5 73.71(9) 4_466 . ?
O2 K1 N4 22.37(8) 4_466 4_466 ?
O2 K1 N5 98.89(9) 4_466 4_566 ?
O2 K1 N7 116.70(10) 4_466 4_566 ?
O2 K1 N8 97.23(11) 4_466 4_566 ?
O3 K1 K1 160.44(7) 4_566 4_466 ?
O3 K1 K1 36.02(7) . 4_466 ?
O3 K1 O1 67.88(9) . 4_466 ?
O3 K1 O1 160.06(9) 4_566 4_466 ?
O3 K1 O2 111.98(9) . 4_466 ?
O3 K1 O2 121.27(9) 4_566 4_466 ?
O3 K1 O3 124.67(8) . 4_566 ?
O3 K1 O4 45.06(9) 4_566 4_566 ?
O3 K1 O4 166.92(9) . 4_566 ?
O3 K1 O5 121.72(10) . . ?
O3 K1 O5 88.15(9) 4_566 . ?
O3 K1 N4 89.91(9) . 4_466 ?
O3 K1 N4 143.47(9) 4_566 4_466 ?
O3 K1 N5 22.38(9) 4_566 4_566 ?
O3 K1 N5 145.25(9) . 4_566 ?
O3 K1 N7 72.40(10) 4_566 4_566 ?
O3 K1 N7 71.39(10) . 4_566 ?
O3 K1 N8 94.56(10) . 4_566 ?
O3 K1 N8 66.13(11) 4_566 4_566 ?
O4 K1 K1 154.45(7) 4_566 4_466 ?
O4 K1 O1 119.58(9) 4_566 4_466 ?
O4 K1 N4 98.85(9) 4_566 4_466 ?
O4 K1 N5 23.13(8) 4_566 4_566 ?
O4 K1 N7 96.04(10) 4_566 4_566 ?
O5 K1 K1 101.54(7) . 4_466 ?
O5 K1 O1 97.66(9) . 4_466 ?
O5 K1 O4 69.53(9) . 4_566 ?
O5 K1 N4 81.70(9) . 4_466 ?
O5 K1 N5 81.21(9) . 4_566 ?
O5 K1 N7 160.54(11) . 4_566 ?
O5 K1 N8 143.56(10) . 4_566 ?
N4 K1 K1 55.68(6) 4_466 4_466 ?
N5 K1 K1 174.98(8) 4_566 4_466 ?
N5 K1 N4 121.10(9) 4_566 4_466 ?
N7 K1 K1 96.88(8) 4_566 4_466 ?
N7 K1 N4 114.31(10) 4_566 4_466 ?
N7 K1 N5 80.89(10) 4_566 4_566 ?
N8 K1 K1 111.12(9) 4_566 4_466 ?
N8 K1 O1 99.40(11) 4_566 4_466 ?
N8 K1 O4 74.05(10) 4_566 4_566 ?
N8 K1 N4 103.38(11) 4_566 4_466 ?
N8 K1 N5 65.11(10) 4_566 4_566 ?
N8 K1 N7 26.17(10) 4_566 4_566 ?
O4 K2 K2 111.48(7) 1_545 4_456 ?
O4 K2 O8 87.44(9) 1_545 4_556 ?
O4 K2 N2 58.69(9) 1_545 1_545 ?
O4 K2 N3 139.97(9) 1_545 4_466 ?
O4 K2 N9 81.50(9) 1_545 4_456 ?
O4 K2 N10 88.58(9) 1_545 4_556 ?
O5 K2 K2 78.49(6) 4_456 4_456 ?
O5 K2 O4 69.18(8) 4_456 1_545 ?
O5 K2 O8 81.23(9) 4_456 4_556 ?
O5 K2 N2 127.71(9) 4_456 1_545 ?
O5 K2 N3 71.17(9) 4_456 4_466 ?
O5 K2 N9 23.13(8) 4_456 4_456 ?
O5 K2 N10 102.84(9) 4_456 4_556 ?
O6 K2 K2 85.91(7) . 4_456 ?
O6 K2 K2 34.63(5) 4_456 4_456 ?
O6 K2 O4 127.58(9) . 1_545 ?
O6 K2 O4 87.67(9) 4_456 1_545 ?
O6 K2 O5 160.98(9) . 4_456 ?
O6 K2 O5 44.90(8) 4_456 4_456 ?
O6 K2 O6 120.53(7) . 4_456 ?
O6 K2 O7 162.99(10) 4_456 4_556 ?
O6 K2 O7 65.35(9) . 4_556 ?
O6 K2 O8 123.42(9) 4_456 4_556 ?
O6 K2 O8 106.39(9) . 4_556 ?
O6 K2 N2 130.81(10) 4_456 1_545 ?
O6 K2 N2 70.23(9) . 1_545 ?
O6 K2 N3 59.81(9) 4_456 4_466 ?
O6 K2 N3 90.92(9) . 4_466 ?
O6 K2 N9 139.85(9) . 4_456 ?
O6 K2 N9 22.48(8) 4_456 4_456 ?
O6 K2 N10 146.13(9) 4_456 4_556 ?
O6 K2 N10 87.75(9) . 4_556 ?
O7 K2 K2 145.89(7) 4_556 4_456 ?
O7 K2 K2 35.60(7) . 4_456 ?
O7 K2 O4 109.05(10) . 1_545 ?
O7 K2 O4 100.90(9) 4_556 1_545 ?
O7 K2 O5 110.78(9) . 4_456 ?
O7 K2 O5 124.72(9) 4_556 4_456 ?
O7 K2 O6 66.06(9) . 4_456 ?
O7 K2 O6 58.12(9) . . ?
O7 K2 O7 123.29(7) . 4_556 ?
O7 K2 O8 162.04(10) . 4_556 ?
O7 K2 O8 43.51(8) 4_556 4_556 ?
O7 K2 N2 90.54(10) . 1_545 ?
O7 K2 N2 65.70(10) 4_556 1_545 ?
O7 K2 N3 80.16(10) . 4_466 ?
O7 K2 N3 105.82(10) 4_556 4_466 ?
O7 K2 N9 88.46(9) . 4_456 ?
O7 K2 N9 143.94(9) 4_556 4_456 ?
O7 K2 N10 22.45(9) 4_556 4_556 ?
O7 K2 N10 145.74(9) . 4_556 ?
O8 K2 K2 144.66(7) 4_556 4_456 ?
O8 K2 N2 92.23(10) 4_556 1_545 ?
O8 K2 N3 91.83(9) 4_556 4_466 ?
O8 K2 N9 101.35(9) 4_556 4_456 ?
O8 K2 N10 22.74(9) 4_556 4_556 ?
N2 K2 K2 123.04(8) 1_545 4_456 ?
N2 K2 N3 161.10(9) 1_545 4_466 ?
N2 K2 N9 137.32(10) 1_545 4_456 ?
N2 K2 N10 73.46(10) 1_545 4_556 ?
N3 K2 K2 54.27(7) 4_466 4_456 ?
N9 K2 K2 55.36(6) 4_456 4_456 ?
N9 K2 N3 59.42(9) 4_456 4_466 ?
N9 K2 N10 123.91(9) 4_456 4_556 ?
N10 K2 K2 158.49(7) 4_556 4_456 ?
N10 K2 N3 105.38(9) 4_556 4_466 ?
K1 O1 K1 104.80(10) . 4_566 ?
N4 O1 K1 140.6(3) . . ?
N4 O1 K1 92.9(2) . 4_566 ?
N4 O2 K1 97.4(2) . 4_566 ?
K1 O3 K1 108.92(10) . 4_466 ?
N5 O3 K1 144.9(3) . . ?
N5 O3 K1 99.3(2) . 4_466 ?
K2 O4 K1 109.68(11) 1_565 4_466 ?
N5 O4 K1 92.8(2) . 4_466 ?
N5 O4 K2 111.2(2) . 1_565 ?
K1 O5 K2 111.40(11) . 4_556 ?
N9 O5 K1 118.7(2) . . ?
N9 O5 K2 93.5(2) . 4_556 ?
K2 O6 K2 109.51(9) . 4_556 ?
N9 O6 K2 96.8(2) . 4_556 ?
N9 O6 K2 141.9(2) . . ?
K2 O7 K2 110.79(10) . 4_456 ?
N10 O7 K2 146.4(3) . . ?
N10 O7 K2 97.4(2) . 4_456 ?
N10 O8 K2 89.1(2) . 4_456 ?
C3 N1 C2 116.2(3) . . ?
N3 N2 K2 112.9(3) . 1_565 ?
C2 N2 K2 125.2(3) . 1_565 ?
C2 N2 N3 117.6(3) . . ?
N2 N3 K2 89.0(3) . 4_566 ?
C4 N3 K2 120.3(3) . 4_566 ?
C4 N3 N2 119.8(3) . . ?
O1 N4 K1 64.5(2) . 4_566 ?
O1 N4 C1 122.8(4) . . ?
O2 N4 K1 60.19(19) . 4_566 ?
O2 N4 O1 120.9(4) . . ?
O2 N4 C1 116.3(3) . . ?
C1 N4 K1 160.9(3) . 4_566 ?
O3 N5 K1 58.4(2) . 4_466 ?
O3 N5 O4 120.5(3) . . ?
O3 N5 C1 122.8(3) . . ?
O4 N5 K1 64.0(2) . 4_466 ?
O4 N5 C1 116.6(3) . . ?
C1 N5 K1 168.1(3) . 4_466 ?
C9 N6 C8 116.2(4) . . ?
N8 N7 K1 69.2(2) . 4_466 ?
C8 N7 K1 172.3(3) . 4_466 ?
C8 N7 N8 117.7(4) . . ?
N7 N8 K1 84.7(2) . 4_466 ?
C10 N8 K1 155.5(3) . 4_466 ?
C10 N8 N7 119.7(4) . . ?
O5 N9 K2 63.3(2) . 4_556 ?
O5 N9 C7 114.9(3) . . ?
O6 N9 K2 60.7(2) . 4_556 ?
O6 N9 O5 120.9(3) . . ?
O6 N9 C7 124.1(3) . . ?
C7 N9 K2 162.7(3) . 4_556 ?
O7 N10 K2 60.2(2) . 4_456 ?
O7 N10 O8 120.5(4) . . ?
O7 N10 C7 123.0(4) . . ?
O8 N10 K2 68.1(2) . 4_456 ?
O8 N10 C7 116.5(3) . . ?
C7 N10 K2 152.4(3) . 4_456 ?
N4 C1 C2 116.9(4) . . ?
N5 C1 N4 121.4(3) . . ?
N5 C1 C2 121.7(4) . . ?
N1 C2 C1 115.6(3) . . ?
N2 C2 N1 126.4(4) . . ?
N2 C2 C1 118.1(4) . . ?
N1 C3 C4 119.1(4) . . ?
N1 C3 C5 118.8(4) . . ?
C4 C3 C5 122.1(4) . . ?
N3 C4 C3 120.9(4) . . ?
N3 C4 C6 116.8(4) . . ?
C3 C4 C6 122.3(4) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N9 C7 N10 122.8(3) . . ?
N9 C7 C8 118.3(4) . . ?
N10 C7 C8 118.9(4) . . ?
N6 C8 C7 117.0(3) . . ?
N7 C8 N6 126.5(4) . . ?
N7 C8 C7 116.5(4) . . ?
N6 C9 C10 119.2(4) . . ?
N6 C9 C31 118.7(4) . . ?
C10 C9 C31 122.1(4) . . ?
N8 C10 C9 120.7(4) . . ?
N8 C10 C11 117.0(4) . . ?
C9 C10 C11 122.3(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C31 H31A 109.5 . . ?
C9 C31 H31B 109.5 . . ?
C9 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O1 N4 K1 117.8(4) . . . 4_566 ?
K1 O1 N4 O2 139.6(4) . . . . ?
K1 O1 N4 O2 21.8(4) 4_566 . . . ?
K1 O1 N4 C1 -159.7(3) 4_566 . . . ?
K1 O1 N4 C1 -42.0(6) . . . . ?
K1 O2 N4 O1 -22.7(4) 4_566 . . . ?
K1 O2 N4 C1 158.7(3) 4_566 . . . ?
K1 O3 N5 K1 143.4(5) . . . 4_466 ?
K1 O3 N5 O4 16.5(4) 4_466 . . . ?
K1 O3 N5 O4 159.9(3) . . . . ?
K1 O3 N5 C1 -166.0(3) 4_466 . . . ?
K1 O3 N5 C1 -22.5(7) . . . . ?
K1 O4 N5 O3 -15.6(4) 4_466 . . . ?
K1 O4 N5 C1 166.7(3) 4_466 . . . ?
K1 O5 N9 K2 -116.8(2) . . . 4_556 ?
K1 O5 N9 O6 -96.8(4) . . . . ?
K1 O5 N9 C7 82.3(4) . . . . ?
K1 N4 C1 N5 -85.6(8) 4_566 . . . ?
K1 N4 C1 C2 94.1(8) 4_566 . . . ?
K1 N5 C1 N4 -86.0(13) 4_466 . . . ?
K1 N5 C1 C2 94.3(12) 4_466 . . . ?
K1 N7 N8 C10 -177.3(5) 4_466 . . . ?
K1 N8 C10 C9 -171.3(5) 4_466 . . . ?
K1 N8 C10 C11 8.7(10) 4_466 . . . ?
K2 O4 N5 K1 112.39(18) 1_565 . . 4_466 ?
K2 O4 N5 O3 96.8(3) 1_565 . . . ?
K2 O4 N5 C1 -80.9(4) 1_565 . . . ?
K2 O5 N9 O6 20.0(4) 4_556 . . . ?
K2 O5 N9 C7 -160.9(3) 4_556 . . . ?
K2 O6 N9 K2 -134.2(4) . . . 4_556 ?
K2 O6 N9 O5 -154.8(3) . . . . ?
K2 O6 N9 O5 -20.5(4) 4_556 . . . ?
K2 O6 N9 C7 26.2(6) . . . . ?
K2 O6 N9 C7 160.5(3) 4_556 . . . ?
K2 O7 N10 K2 -147.3(5) . . . 4_456 ?
K2 O7 N10 O8 179.5(3) . . . . ?
K2 O7 N10 O8 -33.2(4) 4_456 . . . ?
K2 O7 N10 C7 0.3(7) . . . . ?
K2 O7 N10 C7 147.7(4) 4_456 . . . ?
K2 O8 N10 O7 30.8(4) 4_456 . . . ?
K2 O8 N10 C7 -150.1(3) 4_456 . . . ?
K2 N2 N3 K2 77.55(19) 1_565 . . 4_566 ?
K2 N2 N3 C4 -157.6(4) 1_565 . . . ?
K2 N2 C2 N1 151.9(3) 1_565 . . . ?
K2 N2 C2 C1 -28.6(6) 1_565 . . . ?
K2 N3 C4 C3 110.0(4) 4_566 . . . ?
K2 N3 C4 C6 -68.7(5) 4_566 . . . ?
K2 N9 C7 N10 96.6(9) 4_556 . . . ?
K2 N9 C7 C8 -81.8(9) 4_556 . . . ?
K2 N10 C7 N9 80.5(7) 4_456 . . . ?
K2 N10 C7 C8 -101.2(6) 4_456 . . . ?
O1 N4 C1 N5 21.4(6) . . . . ?
O1 N4 C1 C2 -158.9(4) . . . . ?
O2 N4 C1 N5 -160.1(4) . . . . ?
O2 N4 C1 C2 19.6(5) . . . . ?
O3 N5 C1 N4 6.0(6) . . . . ?
O3 N5 C1 C2 -173.7(4) . . . . ?
O4 N5 C1 N4 -176.3(4) . . . . ?
O4 N5 C1 C2 4.0(6) . . . . ?
O5 N9 C7 N10 176.5(4) . . . . ?
O5 N9 C7 C8 -1.9(5) . . . . ?
O6 N9 C7 N10 -4.4(7) . . . . ?
O6 N9 C7 C8 177.2(4) . . . . ?
O7 N10 C7 N9 -7.2(7) . . . . ?
O7 N10 C7 C8 171.1(4) . . . . ?
O8 N10 C7 N9 173.6(4) . . . . ?
O8 N10 C7 C8 -8.0(6) . . . . ?
N1 C3 C4 N3 -1.6(7) . . . . ?
N1 C3 C4 C6 177.0(4) . . . . ?
N2 N3 C4 C3 1.8(7) . . . . ?
N2 N3 C4 C6 -176.8(4) . . . . ?
N3 N2 C2 N1 -3.1(7) . . . . ?
N3 N2 C2 C1 176.4(4) . . . . ?
N4 C1 C2 N1 57.1(5) . . . . ?
N4 C1 C2 N2 -122.4(4) . . . . ?
N5 C1 C2 N1 -123.2(4) . . . . ?
N5 C1 C2 N2 57.3(6) . . . . ?
N6 C9 C10 N8 -1.6(7) . . . . ?
N6 C9 C10 C11 178.4(4) . . . . ?
N7 N8 C10 C9 2.3(7) . . . . ?
N7 N8 C10 C11 -177.8(4) . . . . ?
N8 N7 C8 N6 -0.3(7) . . . . ?
N8 N7 C8 C7 178.7(4) . . . . ?
N9 C7 C8 N6 83.7(5) . . . . ?
N9 C7 C8 N7 -95.5(5) . . . . ?
N10 C7 C8 N6 -94.8(5) . . . . ?
N10 C7 C8 N7 86.1(5) . . . . ?
C2 N1 C3 C4 -0.8(6) . . . . ?
C2 N1 C3 C5 179.6(4) . . . . ?
C2 N2 N3 K2 -124.5(4) . . . 4_566 ?
C2 N2 N3 C4 0.4(7) . . . . ?
C3 N1 C2 N2 3.2(7) . . . . ?
C3 N1 C2 C1 -176.2(4) . . . . ?
C5 C3 C4 N3 178.0(4) . . . . ?
C5 C3 C4 C6 -3.4(7) . . . . ?
C8 N6 C9 C10 0.0(6) . . . . ?
C8 N6 C9 C31 -179.4(4) . . . . ?
C8 N7 N8 K1 176.0(4) . . . 4_466 ?
C8 N7 N8 C10 -1.3(6) . . . . ?
C9 N6 C8 N7 0.9(6) . . . . ?
C9 N6 C8 C7 -178.1(4) . . . . ?
C31 C9 C10 N8 177.9(4) . . . . ?
C31 C9 C10 C11 -2.1(7) . . . . ?

_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 'A70 Needle'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.779
_oxdiff_exptl_absorpt_empirical_full_min 0.557
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.625(15)
2 0.375(15)

####################################################################### 
# 
# 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_js1219a
_database_code_depnum_ccdc_archive 'CCDC 1975379'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H4 F5 N5 O4'
_chemical_formula_sum            'C9 H4 F5 N5 O4'
_chemical_formula_weight         341.17
_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'
F F 0.0727 0.0534 '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                   14.2809(2)
_cell_length_b                   6.21890(10)
_cell_length_c                   14.2905(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.8050(10)
_cell_angle_gamma                90
_cell_volume                     1161.19(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      72.35
_cell_measurement_theta_min      6.23
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.647
_exptl_absorpt_coefficient_mu    1.854
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6670
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0551 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.8851.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0240
-1.00 0.00 0.00 0.0410
0.00 0.00 -1.00 0.1080
0.00 0.00 1.00 0.0910
0.00 -1.00 0.00 0.0870
0.00 1.00 0.00 0.0780

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.082
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K. A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil. Data were measured using omega and phi scans of 1.0\ per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Α to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick. 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  0.0298
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7683
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.357
_diffrn_reflns_theta_min         6.228
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1966
_reflns_number_total             2246
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0065(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   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.103
_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)+(0.0641P)²+0.3188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
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 was found 
by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_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
F1 F 0.94950(8) 0.19630(18) 0.54531(8) 0.0291(3) Uani 1 1 d . . . . .
F2 F 1.09628(8) 0.26842(18) 0.47770(9) 0.0324(3) Uani 1 1 d . . . . .
F3 F 1.04576(9) 0.4105(2) 0.28247(9) 0.0380(3) Uani 1 1 d . . . . .
F4 F 0.84663(9) 0.47788(19) 0.15781(8) 0.0337(3) Uani 1 1 d . . . . .
F5 F 0.69949(7) 0.39151(17) 0.21973(7) 0.0268(3) Uani 1 1 d . . . . .
O1 O 0.26582(9) 0.3566(2) 0.24861(9) 0.0287(3) Uani 1 1 d . . . . .
O2 O 0.26581(10) 0.5042(2) 0.38568(10) 0.0292(3) Uani 1 1 d . . . . .
O3 O 0.35294(10) 0.2145(2) 0.52673(10) 0.0285(3) Uani 1 1 d . . . . .
O4 O 0.51554(9) 0.2127(2) 0.56245(9) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.57908(11) 0.2645(2) 0.41693(11) 0.0205(3) Uani 1 1 d . . . . .
H1 H 0.5976(16) 0.249(3) 0.4813(17) 0.023(5) Uiso 1 1 d . . . . .
N2 N 0.64613(11) 0.2810(2) 0.37003(11) 0.0220(3) Uani 1 1 d . . . . .
N3 N 0.30579(10) 0.3902(2) 0.34186(11) 0.0206(3) Uani 1 1 d . . . . .
N4 N 0.42410(10) 0.2432(2) 0.50051(11) 0.0192(3) Uani 1 1 d . . . . .
N5 N 0.45397(12) 0.3194(3) 0.25795(11) 0.0247(3) Uani 1 1 d . . . . .
H5A H 0.390(2) 0.324(5) 0.216(2) 0.061(9) Uiso 1 1 d . . . . .
H5B H 0.5004(19) 0.318(4) 0.2354(17) 0.028(5) Uiso 1 1 d . . . . .
C1 C 0.47980(13) 0.2930(2) 0.35689(12) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.40468(12) 0.3013(3) 0.40038(12) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.74108(13) 0.2584(3) 0.42759(13) 0.0214(4) Uani 1 1 d . . . . .
H3 H 0.761634 0.220658 0.497494 0.026 Uiso 1 1 calc R U . . .
C4 C 0.81776(13) 0.2906(2) 0.38575(13) 0.0202(4) Uani 1 1 d . . . . .
C5 C 0.92178(13) 0.2600(3) 0.44786(13) 0.0219(4) Uani 1 1 d . . . . .
C6 C 0.99822(13) 0.2979(3) 0.41501(14) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.97267(13) 0.3713(3) 0.31643(14) 0.0247(4) Uani 1 1 d . . . . .
C8 C 0.87197(14) 0.4043(3) 0.25307(13) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.79584(13) 0.3618(3) 0.28655(13) 0.0209(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.345(2) . ?
F2 C6 1.336(2) . ?
F3 C7 1.3392(19) . ?
F4 C8 1.340(2) . ?
F5 C9 1.3335(19) . ?
O1 N3 1.2374(18) . ?
O2 N3 1.2290(19) . ?
O3 N4 1.2298(19) . ?
O4 N4 1.2616(19) . ?
N1 H1 0.85(2) . ?
N1 N2 1.376(2) . ?
N1 C1 1.340(2) . ?
N2 C3 1.279(2) . ?
N3 C2 1.430(2) . ?
N4 C2 1.391(2) . ?
N5 H5A 0.87(3) . ?
N5 H5B 0.85(2) . ?
N5 C1 1.320(2) . ?
C1 C2 1.442(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.458(2) . ?
C4 C5 1.402(2) . ?
C4 C9 1.395(2) . ?
C5 C6 1.372(2) . ?
C6 C7 1.382(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.379(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 H1 124.0(14) . . ?
C1 N1 H1 119.5(14) . . ?
C1 N1 N2 116.27(14) . . ?
C3 N2 N1 116.37(15) . . ?
O1 N3 C2 118.82(14) . . ?
O2 N3 O1 122.61(14) . . ?
O2 N3 C2 118.50(14) . . ?
O3 N4 O4 120.86(14) . . ?
O3 N4 C2 120.34(13) . . ?
O4 N4 C2 118.74(13) . . ?
H5A N5 H5B 121(2) . . ?
C1 N5 H5A 120.2(19) . . ?
C1 N5 H5B 118.9(15) . . ?
N1 C1 C2 120.52(15) . . ?
N5 C1 N1 117.93(15) . . ?
N5 C1 C2 121.52(15) . . ?
N3 C2 C1 119.51(14) . . ?
N4 C2 N3 116.21(14) . . ?
N4 C2 C1 124.07(14) . . ?
N2 C3 H3 120.1 . . ?
N2 C3 C4 119.88(16) . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.06(16) . . ?
C9 C4 C3 124.25(16) . . ?
C9 C4 C5 115.61(15) . . ?
F1 C5 C4 119.29(15) . . ?
F1 C5 C6 117.58(15) . . ?
C6 C5 C4 123.10(16) . . ?
F2 C6 C5 120.70(16) . . ?
F2 C6 C7 120.18(15) . . ?
C5 C6 C7 119.11(16) . . ?
F3 C7 C6 120.38(16) . . ?
F3 C7 C8 119.78(16) . . ?
C8 C7 C6 119.84(16) . . ?
F4 C8 C7 120.22(15) . . ?
F4 C8 C9 119.37(15) . . ?
C7 C8 C9 120.40(16) . . ?
F5 C9 C4 121.00(15) . . ?
F5 C9 C8 117.09(15) . . ?
C8 C9 C4 121.91(16) . . ?

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 O4 0.85(2) 1.97(2) 2.6028(19) 130.4(19) . yes
N5 H5A O1 0.87(3) 2.01(3) 2.646(2) 129(3) . yes
N5 H5A O3 0.87(3) 2.55(3) 3.032(2) 116(2) 4_565 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
F1 C5 C6 F2 1.2(2) . . . . ?
F1 C5 C6 C7 -177.60(15) . . . . ?
F2 C6 C7 F3 1.0(3) . . . . ?
F2 C6 C7 C8 -178.98(15) . . . . ?
F3 C7 C8 F4 -0.7(3) . . . . ?
F3 C7 C8 C9 179.10(15) . . . . ?
F4 C8 C9 F5 1.8(2) . . . . ?
F4 C8 C9 C4 -178.25(15) . . . . ?
O1 N3 C2 N4 -147.79(15) . . . . ?
O1 N3 C2 C1 37.1(2) . . . . ?
O2 N3 C2 N4 35.2(2) . . . . ?
O2 N3 C2 C1 -139.91(16) . . . . ?
O3 N4 C2 N3 19.3(2) . . . . ?
O3 N4 C2 C1 -165.91(15) . . . . ?
O4 N4 C2 N3 -163.44(14) . . . . ?
O4 N4 C2 C1 11.4(2) . . . . ?
N1 N2 C3 C4 -175.07(13) . . . . ?
N1 C1 C2 N3 162.52(14) . . . . ?
N1 C1 C2 N4 -12.1(2) . . . . ?
N2 N1 C1 N5 4.5(2) . . . . ?
N2 N1 C1 C2 -173.49(13) . . . . ?
N2 C3 C4 C5 -178.18(15) . . . . ?
N2 C3 C4 C9 5.1(3) . . . . ?
N5 C1 C2 N3 -15.4(2) . . . . ?
N5 C1 C2 N4 169.94(15) . . . . ?
C1 N1 N2 C3 178.57(14) . . . . ?
C3 C4 C5 F1 1.4(2) . . . . ?
C3 C4 C5 C6 -176.61(15) . . . . ?
C3 C4 C9 F5 -4.8(2) . . . . ?
C3 C4 C9 C8 175.28(15) . . . . ?
C4 C5 C6 F2 179.24(14) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C4 C9 F5 178.32(14) . . . . ?
C5 C4 C9 C8 -1.6(2) . . . . ?
C5 C6 C7 F3 179.73(15) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 F4 179.21(15) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 F5 -178.00(14) . . . . ?
C7 C8 C9 C4 1.9(3) . . . . ?
C9 C4 C5 F1 178.45(14) . . . . ?
C9 C4 C5 C6 0.4(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AKC-162
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_js220c
_database_code_depnum_ccdc_archive 'CCDC 2154059'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-02-10
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 F3 N5 O5'
_chemical_formula_sum            'C7 H8 F3 N5 O5'
_chemical_formula_weight         299.18
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6530(4)
_cell_length_b                   8.3737(4)
_cell_length_c                   10.1818(6)
_cell_angle_alpha                108.537(4)
_cell_angle_beta                 105.840(4)
_cell_angle_gamma                96.862(3)
_cell_volume                     579.73(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4621
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      4.85
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.524
_exptl_absorpt_coefficient_mu    1.557
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0705 after correction.
The Ratio of minimum to maximum transmission is 0.7436.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.0420
1.00 0.00 -1.00 0.0070
0.00 0.00 1.00 0.1400
0.00 0.00 -1.00 0.1400
1.00 4.00 -1.00 0.1490
-1.00 -4.00 1.00 0.1970
1.00 -3.00 2.00 0.2520
1.00 4.00 4.00 0.1570
-2.00 1.00 -4.00 0.1540
-1.00 4.00 3.00 0.1440
1.00 -2.00 0.00 0.2060
-1.00 2.00 0.00 0.1370

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.084
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  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  0.0501
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7520
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.151
_diffrn_reflns_theta_min         4.853
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1816
_reflns_number_total             2067
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.037
_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)+(0.0595P)²+0.1871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
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 was found 
by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.66680(17) 0.58140(17) 0.42813(12) 0.0435(3) Uani 1 1 d . . . . .
F2 F 0.76378(15) 0.73544(17) 0.31732(16) 0.0474(4) Uani 1 1 d . . . . .
F3 F 0.67245(15) 0.45941(16) 0.21096(12) 0.0380(3) Uani 1 1 d . . . . .
O1 O 0.42522(17) 0.63254(16) 0.10406(13) 0.0246(3) Uani 1 1 d . . . . .
O2 O -0.09779(18) 0.31223(17) 0.00469(15) 0.0319(3) Uani 1 1 d . . . . .
O3 O -0.22957(17) 0.11720(17) 0.07045(16) 0.0323(3) Uani 1 1 d . . . . .
O4 O 0.0176(2) 0.00730(19) 0.24482(16) 0.0373(4) Uani 1 1 d . . . . .
O5 O 0.30743(18) 0.13320(18) 0.29476(15) 0.0341(3) Uani 1 1 d . . . . .
N1 N 0.3014(2) 0.47538(18) 0.22982(15) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.2047(2) 0.5246(2) 0.33115(16) 0.0265(4) Uani 1 1 d . . . . .
N3 N 0.3070(2) 0.2602(2) 0.02111(17) 0.0264(4) Uani 1 1 d . . . . .
N4 N -0.0877(2) 0.20567(19) 0.07096(16) 0.0249(3) Uani 1 1 d . . . . .
N5 N 0.1368(2) 0.10761(19) 0.23023(16) 0.0263(4) Uani 1 1 d . . . . .
C1 C 0.4412(2) 0.6236(2) 0.23940(19) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.4034(3) 0.7746(2) 0.3525(2) 0.0286(4) Uani 1 1 d . . . . .
H2A H 0.351(3) 0.852(3) 0.308(2) 0.028(5) Uiso 1 1 d . . . . .
H2B H 0.518(4) 0.841(3) 0.438(3) 0.043(6) Uiso 1 1 d . . . . .
C3 C 0.2634(3) 0.6884(2) 0.40026(19) 0.0278(4) Uani 1 1 d . . . . .
C4 C 0.6387(3) 0.5980(2) 0.2994(2) 0.0295(4) Uani 1 1 d . . . . .
C5 C 0.1936(3) 0.7823(3) 0.5189(2) 0.0385(5) Uani 1 1 d . . . . .
H5A H 0.091(3) 0.709(3) 0.532(3) 0.035(6) Uiso 1 1 d . . . . .
H5B H 0.299(4) 0.835(4) 0.608(3) 0.053(7) Uiso 1 1 d . . . . .
H5C H 0.144(4) 0.880(4) 0.498(3) 0.045(7) Uiso 1 1 d . . . . .
C6 C 0.2415(2) 0.3167(2) 0.12829(19) 0.0236(4) Uani 1 1 d . . . . .
C7 C 0.0894(2) 0.1978(2) 0.13704(19) 0.0236(4) Uani 1 1 d . . . . .
H3A H 0.388(4) 0.312(3) 0.003(3) 0.032(6) Uiso 1 1 d . . . . .
H3B H 0.264(4) 0.158(4) -0.032(3) 0.037(6) Uiso 1 1 d . . . . .
H1 H 0.323(4) 0.655(3) 0.067(3) 0.043(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.324(2) . ?
F2 C4 1.335(2) . ?
F3 C4 1.326(2) . ?
O1 C1 1.377(2) . ?
O1 H1 0.85(3) . ?
O2 N4 1.276(2) . ?
O3 N4 1.237(2) . ?
O4 N5 1.237(2) . ?
O5 N5 1.248(2) . ?
N1 N2 1.415(2) . ?
N1 C1 1.498(2) . ?
N1 C6 1.329(2) . ?
N2 C3 1.283(2) . ?
N3 C6 1.301(2) . ?
N3 H3A 0.81(3) . ?
N3 H3B 0.82(3) . ?
N4 C7 1.359(2) . ?
N5 C7 1.391(2) . ?
C1 C2 1.533(2) . ?
C1 C4 1.537(2) . ?
C2 H2A 0.96(2) . ?
C2 H2B 1.00(3) . ?
C2 C3 1.493(3) . ?
C3 C5 1.487(3) . ?
C5 H5A 1.00(2) . ?
C5 H5B 0.96(3) . ?
C5 H5C 1.00(3) . ?
C6 C7 1.480(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 111.6(17) . . ?
N2 N1 C1 112.89(13) . . ?
C6 N1 N2 117.84(14) . . ?
C6 N1 C1 128.51(14) . . ?
C3 N2 N1 107.04(14) . . ?
C6 N3 H3A 127.9(16) . . ?
C6 N3 H3B 115.8(17) . . ?
H3A N3 H3B 116(2) . . ?
O2 N4 C7 113.97(14) . . ?
O3 N4 O2 121.37(15) . . ?
O3 N4 C7 124.65(15) . . ?
O4 N5 O5 123.11(15) . . ?
O4 N5 C7 121.88(15) . . ?
O5 N5 C7 114.99(14) . . ?
O1 C1 N1 112.32(13) . . ?
O1 C1 C2 117.65(15) . . ?
O1 C1 C4 105.88(14) . . ?
N1 C1 C2 100.82(13) . . ?
N1 C1 C4 109.30(14) . . ?
C2 C1 C4 110.76(15) . . ?
C1 C2 H2A 111.1(13) . . ?
C1 C2 H2B 112.4(15) . . ?
H2A C2 H2B 110(2) . . ?
C3 C2 C1 103.61(14) . . ?
C3 C2 H2A 109.9(13) . . ?
C3 C2 H2B 110.0(15) . . ?
N2 C3 C2 115.31(16) . . ?
N2 C3 C5 121.14(18) . . ?
C5 C3 C2 123.55(17) . . ?
F1 C4 F2 108.25(15) . . ?
F1 C4 F3 107.42(15) . . ?
F1 C4 C1 110.90(15) . . ?
F2 C4 C1 109.42(15) . . ?
F3 C4 F2 107.64(16) . . ?
F3 C4 C1 113.05(15) . . ?
C3 C5 H5A 114.3(14) . . ?
C3 C5 H5B 107.7(17) . . ?
C3 C5 H5C 110.3(15) . . ?
H5A C5 H5B 112(2) . . ?
H5A C5 H5C 107(2) . . ?
H5B C5 H5C 106(2) . . ?
N1 C6 C7 117.82(15) . . ?
N3 C6 N1 124.09(16) . . ?
N3 C6 C7 118.09(16) . . ?
N4 C7 N5 124.43(15) . . ?
N4 C7 C6 116.73(15) . . ?
N5 C7 C6 118.01(15) . . ?

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
N3 H3A F3 0.81(3) 2.43(2) 2.8682(19) 115(2) . yes
N3 H3A O1 0.81(3) 2.11(3) 2.889(2) 161(2) 2_665 yes
N3 H3A O1 0.81(3) 2.50(2) 2.913(2) 113.2(19) . yes
N3 H3B O3 0.82(3) 2.18(3) 2.930(2) 152(2) 2 yes
O1 H1 O2 0.85(3) 1.77(3) 2.6090(18) 174(2) 2_565 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 C1 C2 C3 127.80(15) . . . . ?
O1 C1 C4 F1 -177.75(14) . . . . ?
O1 C1 C4 F2 62.91(18) . . . . ?
O1 C1 C4 F3 -57.03(19) . . . . ?
O2 N4 C7 N5 171.86(15) . . . . ?
O2 N4 C7 C6 2.5(2) . . . . ?
O3 N4 C7 N5 -9.4(3) . . . . ?
O3 N4 C7 C6 -178.77(15) . . . . ?
O4 N5 C7 N4 10.0(3) . . . . ?
O4 N5 C7 C6 179.20(15) . . . . ?
O5 N5 C7 N4 -171.35(16) . . . . ?
O5 N5 C7 C6 -2.2(2) . . . . ?
N1 N2 C3 C2 1.9(2) . . . . ?
N1 N2 C3 C5 -178.26(17) . . . . ?
N1 C1 C2 C3 5.34(17) . . . . ?
N1 C1 C4 F1 -56.55(19) . . . . ?
N1 C1 C4 F2 -175.89(14) . . . . ?
N1 C1 C4 F3 64.17(19) . . . . ?
N1 C6 C7 N4 86.3(2) . . . . ?
N1 C6 C7 N5 -83.7(2) . . . . ?
N2 N1 C1 O1 -130.98(15) . . . . ?
N2 N1 C1 C2 -4.88(18) . . . . ?
N2 N1 C1 C4 111.82(15) . . . . ?
N2 N1 C6 N3 173.73(16) . . . . ?
N2 N1 C6 C7 -5.5(2) . . . . ?
N3 C6 C7 N4 -93.0(2) . . . . ?
N3 C6 C7 N5 97.0(2) . . . . ?
C1 N1 N2 C3 2.15(19) . . . . ?
C1 N1 C6 N3 4.5(3) . . . . ?
C1 N1 C6 C7 -174.75(15) . . . . ?
C1 C2 C3 N2 -4.9(2) . . . . ?
C1 C2 C3 C5 175.23(18) . . . . ?
C2 C1 C4 F1 53.7(2) . . . . ?
C2 C1 C4 F2 -65.7(2) . . . . ?
C2 C1 C4 F3 174.38(15) . . . . ?
C4 C1 C2 C3 -110.28(16) . . . . ?
C6 N1 N2 C3 -168.71(15) . . . . ?
C6 N1 C1 O1 38.7(2) . . . . ?
C6 N1 C1 C2 164.78(16) . . . . ?
C6 N1 C1 C4 -78.5(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AKC169
_olex2_submission_special_instructions 'No special instructions were received'
