# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2024

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

data_js923a
_database_code_depnum_ccdc_archive 'CCDC 2328918'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2024-01-28 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H N7 O4'
_chemical_formula_sum            'C3 H N7 O4'
_chemical_formula_weight         199.11
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         C3HN7O4
_chemical_oxdiff_usercomment     TVK-0014
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           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                   5.60090(10)
_cell_length_b                   9.84370(10)
_cell_length_c                   12.4975(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     689.032(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4207
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.2570
_cell_measurement_theta_min      3.4790
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    1.566
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 8 0.0655
1 -1 -7 0.0435
1 3 -7 0.0732
-1 -4 6 0.0656
-3 2 1 0.0346
4 -1 0 0.0264
2 -4 -5 0.0536
0 4 6 0.0961
-3 2 -5 0.0400
-1 5 3 0.0966

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.066
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
-1.1969 0.5822 7.6251 0.5867 0.0453 -0.8086
1.2198 -1.3192 -7.4572 -0.4882 -0.0375 0.8719
0.7694 3.4933 -6.5726 -0.9614 -0.0754 0.2645
-0.6536 -4.0846 6.0660 0.9855 0.0774 -0.1509
-3.4983 1.6362 0.7579 -0.0671 0.8452 -0.5302
3.5677 -1.2264 -0.1304 0.0709 -0.8948 0.4408
2.0256 -3.8441 -4.6464 0.0228 -0.2745 0.9613
0.1243 4.1799 6.1291 0.0260 -0.3445 -0.9384
-2.5156 2.3784 -5.0185 -0.6491 0.7600 -0.0327
-1.1397 5.4106 3.4895 -0.3141 0.0404 -0.9485

_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5805
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.149
_diffrn_reflns_theta_min         5.721
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    109.00 178.00   0.50    0.05    --  113.25 100.00 139.00  138
  2  ω    110.00 178.00   0.50    0.05    --  113.25  77.00  90.00  136
  3  ω     42.00  76.00   0.50    0.05    --  113.25 -66.00 125.00   68
  4  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00  90.00   54
  5  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00  30.00   54
  6  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00  60.00   54
  7  ω     42.00  69.00   0.50    0.05    --  113.25 -61.00 -60.00   54
  8  ω     42.00  71.00   0.50    0.05    --  113.25 -62.00 -90.00   58
  9  ω    101.00 178.00   0.50    0.05    --  113.25  45.00-180.00  154
 10  ω     36.00  93.00   0.50    0.05    --   47.11-125.00 120.00  114
 11  ω    -64.00  26.00   0.50    0.05    --  -47.11  62.00  47.00  180
 12  ω    -72.00 -19.00   0.50    0.05    --  -91.75  62.00  47.00  106
 13  ω    -53.00 -20.00   0.50    0.05    --  -91.75  45.00 -60.00   66
 14  ω    -77.00 -19.00   0.50    0.05    --  -91.75  66.00 -99.00  116
 15  ω   -120.00 -35.00   0.50    0.05    --  -47.11 -37.00  60.00  170
 16  ω   -162.00 -87.00   0.50    0.05    --  -91.75-100.00  33.00  150
 17  ω   -119.00 -30.00   0.50    0.05    --  -47.11 -62.00 -90.00  178
 18  ω    153.00 178.00   0.50    0.05    --  113.25  65.00 -99.00   50
 19  ω     40.00  68.00   0.50    0.05    --   47.11-125.00-150.00   56
 20  ω     43.00  70.00   0.50    0.05    --  113.25 -77.00-180.00   54
 21  ω    102.00 148.00   0.50    0.05    --  113.25  30.00  90.00   92
 22  ω    110.00 136.00   0.50    0.05    --  113.25  61.00 -30.00   52
 23  ω    153.00 178.00   0.50    0.05    --  113.25  61.00 -30.00   50
 24  ω     48.00  89.00   0.50    0.05    --  113.25 -77.00  30.00   82
 25  ω     77.00 102.00   0.50    0.05    --  113.25 -94.00-150.00   50
 26  ω    101.00 147.00   0.50    0.05    --  113.25  45.00-150.00   92
;
_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      -0.0166699000
_diffrn_orient_matrix_UB_12      -0.1151712000
_diffrn_orient_matrix_UB_13      0.0831165000
_diffrn_orient_matrix_UB_21      -0.2610210000
_diffrn_orient_matrix_UB_22      -0.0262222000
_diffrn_orient_matrix_UB_23      -0.0330253000
_diffrn_orient_matrix_UB_31      0.0851769000
_diffrn_orient_matrix_UB_32      -0.1026573000
_diffrn_orient_matrix_UB_33      -0.0848301000
_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         0.645
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                1425
_reflns_number_total             1464
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    '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         0.235
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(15)
_refine_ls_extinction_coef       0.0055(8)
_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   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+0.1361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0641
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7720(2) 0.45665(14) 0.92886(11) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.6029(3) 0.60840(13) 0.82778(11) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.4675(3) 0.50457(15) 0.62895(12) 0.0285(4) Uani 1 1 d . . . . .
O4 O 0.0848(3) 0.47357(14) 0.61011(11) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.1579(3) 0.25721(16) 0.88905(12) 0.0161(3) Uani 1 1 d . . . . .
H1 H 0.080(5) 0.209(3) 0.926(2) 0.031(7) Uiso 1 1 d . . . . .
N2 N 0.3513(3) 0.32238(15) 0.92758(12) 0.0156(3) Uani 1 1 d . . . . .
N3 N -0.1064(3) 0.23885(16) 0.74593(11) 0.0193(3) Uani 1 1 d . . . . .
N4 N -0.1201(3) 0.23689(16) 0.64543(12) 0.0180(3) Uani 1 1 d . . . . .
N5 N -0.1609(3) 0.22419(18) 0.55838(14) 0.0252(4) Uani 1 1 d . . . . .
N6 N 0.6124(3) 0.49553(15) 0.86954(11) 0.0160(3) Uani 1 1 d . . . . .
N7 N 0.2745(3) 0.46267(16) 0.65981(12) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.4155(3) 0.40398(17) 0.84942(14) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.2618(3) 0.39524(17) 0.76075(13) 0.0139(4) Uani 1 1 d . . . . .
C3 C 0.0965(3) 0.29716(17) 0.79054(14) 0.0145(4) 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 N6 1.2226(19) . ?
O2 N6 1.2288(19) . ?
O3 N7 1.219(2) . ?
O4 N7 1.236(2) . ?
N1 H1 0.79(3) . ?
N1 N2 1.348(2) . ?
N1 C3 1.337(2) . ?
N2 C1 1.315(2) . ?
N3 N4 1.258(2) . ?
N3 C3 1.390(2) . ?
N4 N5 1.119(2) . ?
N6 C1 1.446(2) . ?
N7 C2 1.427(2) . ?
C1 C2 1.406(2) . ?
C2 C3 1.388(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 121(2) . . ?
C3 N1 H1 125(2) . . ?
C3 N1 N2 113.30(16) . . ?
C1 N2 N1 104.18(15) . . ?
N4 N3 C3 117.16(17) . . ?
N5 N4 N3 170.0(2) . . ?
O1 N6 O2 124.91(16) . . ?
O1 N6 C1 117.89(14) . . ?
O2 N6 C1 117.16(15) . . ?
O3 N7 O4 125.02(15) . . ?
O3 N7 C2 118.77(16) . . ?
O4 N7 C2 116.21(16) . . ?
N2 C1 N6 117.38(15) . . ?
N2 C1 C2 112.39(16) . . ?
C2 C1 N6 129.95(16) . . ?
C1 C2 N7 129.62(17) . . ?
C3 C2 N7 126.42(16) . . ?
C3 C2 C1 103.85(15) . . ?
N1 C3 N3 117.26(16) . . ?
N1 C3 C2 106.25(16) . . ?
C2 C3 N3 136.46(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2 0.79(3) 2.26(3) 2.969(2) 150(2) 4_457 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 N6 C1 N2 33.1(2) . . . . ?
O1 N6 C1 C2 -153.42(18) . . . . ?
O2 N6 C1 N2 -144.89(17) . . . . ?
O2 N6 C1 C2 28.6(3) . . . . ?
O3 N7 C2 C1 23.2(3) . . . . ?
O3 N7 C2 C3 -152.43(18) . . . . ?
O4 N7 C2 C1 -156.94(18) . . . . ?
O4 N7 C2 C3 27.5(3) . . . . ?
N1 N2 C1 N6 176.04(15) . . . . ?
N1 N2 C1 C2 1.5(2) . . . . ?
N2 N1 C3 N3 -177.70(15) . . . . ?
N2 N1 C3 C2 0.5(2) . . . . ?
N2 C1 C2 N7 -177.55(17) . . . . ?
N2 C1 C2 C3 -1.2(2) . . . . ?
N4 N3 C3 N1 -155.70(17) . . . . ?
N4 N3 C3 C2 26.8(3) . . . . ?
N6 C1 C2 N7 8.7(3) . . . . ?
N6 C1 C2 C3 -174.91(17) . . . . ?
N7 C2 C3 N1 176.90(17) . . . . ?
N7 C2 C3 N3 -5.4(3) . . . . ?
C1 C2 C3 N1 0.39(19) . . . . ?
C1 C2 C3 N3 178.1(2) . . . . ?
C3 N1 N2 C1 -1.2(2) . . . . ?
C3 N3 N4 N5 173.4(11) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id TVK-0014
_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 1.168
_oxdiff_exptl_absorpt_empirical_full_min 0.853
####################################################################### 
# 
# 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_js124a
_database_code_depnum_ccdc_archive 'CCDC 2328919'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2024-01-28 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;
_audit_creation_date             2024-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H2 N7 O3, H4 N O'
_chemical_formula_sum            'C3 H6 N8 O4'
_chemical_formula_weight         218.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C3H6N8O4
_chemical_oxdiff_usercomment     TVK-0285-C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.8186(4)
_cell_length_b                   8.1118(6)
_cell_length_c                   8.1248(6)
_cell_angle_alpha                99.814(6)
_cell_angle_beta                 109.959(6)
_cell_angle_gamma                108.879(6)
_cell_volume                     379.22(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3214
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2920
_cell_measurement_theta_min      6.0470
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.684
_exptl_absorpt_coefficient_mu    1.516
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             224
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -5 0.0697
-3 -1 4 0.0672
0 0 4 0.1006
3 1 -4 0.0848
-3 1 2 0.1498
0 -3 2 0.0180
0 3 -2 0.0180

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.036
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
0.6280 -0.2124 -4.9239 -0.3573 0.8621 0.3614
-3.4921 -0.9693 4.0383 0.3004 -0.7285 0.6155
0.0868 0.4477 4.4977 0.3247 -0.7827 -0.5324
3.4277 0.9312 -4.1838 -0.3108 0.7534 -0.5794
-3.0684 1.1728 2.4082 0.5209 -0.3442 0.3891
0.4205 -2.7020 2.2391 -0.3284 -0.5273 0.0229
-0.4295 2.7054 -2.2356 0.3297 0.5269 -0.0214

_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5162
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.287
_diffrn_reflns_theta_min         6.077
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  25.00   0.50    0.05    --   47.11 -19.00-150.00   52
  2  ω    -26.00  40.00   0.50    0.05    --   47.11 -37.00 -90.00  132
  3  ω     -5.00  27.00   0.50    0.05    --   47.11 -19.00   0.00   64
  4  ω    -26.00  23.00   0.50    0.05    --   47.11 -19.00  60.00   98
  5  ω     73.00  98.00   0.50    0.05    --  107.75 -94.00  60.00   50
  6  ω     42.00  73.00   0.50    0.05    --  107.75-125.00   0.00   62
  7  ω     76.00 108.00   0.50    0.05    --  107.75-125.00   0.00   64
  8  ω     45.00  73.00   0.50    0.05    --  107.75-118.00  23.00   56
  9  ω     46.00  74.00   0.50    0.05    --  107.75-125.00 -90.00   56
 10  ω     99.00 129.00   0.50    0.05    --  107.75-157.00-131.00   60
 11  ω     83.00 108.00   0.50    0.05    --  107.75-125.00 -90.00   50
 12  ω     37.00 101.00   0.50    0.05    --  107.75 -94.00 -90.00  128
 13  ω     54.00  90.00   0.50    0.05    --   47.11-157.00-131.00   72
 14  ω     58.00 101.00   0.50    0.05    --  107.75 -94.00-180.00   86
 15  ω     32.00  62.00   0.50    0.05    --   47.11-118.00  23.00   60
 16  ω     41.00  70.00   0.50    0.05    --  107.75 -94.00 120.00   58
 17  ω     73.00 100.00   0.50    0.05    --  107.75 -94.00 120.00   54
 18  ω     79.00 104.00   0.50    0.05    --  107.75 -94.00  30.00   50
 19  ω     75.00 102.00   0.50    0.05    --  107.75 -94.00   0.00   54
 20  ω     38.00  63.00   0.50    0.05    --  107.75 -94.00  30.00   50
 21  ω     41.00  94.00   0.50    0.05    --  107.75 -77.00  30.00  106
 22  ω     74.00 100.00   0.50    0.05    --  107.75 -77.00   0.00   52
 23  ω     40.00  67.00   0.50    0.05    --  107.75 -77.00 -30.00   54
 24  ω     39.00  67.00   0.50    0.05    --  107.75 -61.00 -90.00   56
 25  ω     75.00 100.00   0.50    0.05    --  107.75 -77.00 -60.00   50
 26  ω     41.00  68.00   0.50    0.05    --  107.75 -61.00  30.00   54
 27  ω     35.00  69.00   0.50    0.05    --  107.75 -61.00 120.00   68
 28  ω    122.00 175.00   0.50    0.05    --  107.75  77.00  30.00  106
 29  ω     98.00 134.00   0.50    0.05    --  107.75  45.00 -60.00   72
 30  ω    110.00 176.00   0.50    0.05    --  107.75  77.00-150.00  132
 31  ω     99.00 154.00   0.50    0.05    --  107.75  45.00-150.00  110
 32  ω    141.00 168.00   0.50    0.05    --  107.75  45.00 -60.00   54
 33  ω    110.00 160.00   0.50    0.05    --  107.75  77.00 150.00  100
 34  ω    115.00 140.00   0.50    0.05    --  107.75 118.00 108.00   50
 35  ω    103.00 174.00   0.50    0.05    --  107.75 125.00 -30.00  142
 36  ω    143.00 178.00   0.50    0.05    --  107.75 125.00 -60.00   70
 37  ω     99.00 136.00   0.50    0.05    --  107.75 125.00 -60.00   74
 38  ω    102.00 128.00   0.50    0.05    --  107.75 157.00 -96.00   52
 39  ω    129.00 157.00   0.50    0.05    --  107.75 125.00-150.00   56
 40  ω     -3.00  24.00   0.50    0.05    --  -47.11  19.00 -60.00   54
 41  ω    -36.00 -11.00   0.50    0.05    --  -86.25  30.00 -30.00   50
 42  ω    -39.00 -13.00   0.50    0.05    --  -86.25  30.00  60.00   52
 43  ω    -48.00 -17.00   0.50    0.05    --  -47.11 118.00 108.00   62
 44  ω    -44.00 -19.00   0.50    0.05    --  -47.11 125.00 -30.00   50
 45  ω    -81.00 -53.00   0.50    0.05    --  -47.11 125.00 -30.00   56
 46  ω    -92.00 -67.00   0.50    0.05    --  -47.11 157.00 -96.00   50
 47  ω    -92.00 -67.00   0.50    0.05    --  -86.25 157.00 -96.00   50
 48  ω    -81.00 -49.00   0.50    0.05    --  -86.25 118.00 108.00   64
 49  ω   -116.00 -81.00   0.50    0.05    --  -86.25-118.00  23.00   70
 50  ω    -80.00 -53.00   0.50    0.05    --  -47.11-157.00-131.00   54
 51  ω    -60.00 -26.00   0.50    0.05    --  -47.33  57.00-120.00   68
 52  ω    -14.00  25.00   0.50    0.05    --  -47.33  57.00-120.00   78
 53  ω    -39.00 -14.00   0.50    0.05    --  -86.25  30.00 -60.00   50
 54  ω    131.00 157.00   0.50    0.05    --  107.75  77.00-120.00   52
 55  ω    129.00 176.00   0.50    0.05    --  107.75  45.00 -90.00   94
 56  ω    112.00 138.00   0.50    0.05    --  107.75  61.00  30.00   52
 57  ω     78.00 104.00   0.50    0.05    --  107.75 -94.00 150.00   52
 58  ω     77.00 102.00   0.50    0.05    --  107.75 -94.00-180.00   50
 59  ω    108.00 134.00   0.50    0.05    --  107.75  61.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0636832000
_diffrn_orient_matrix_UB_12      0.1593227000
_diffrn_orient_matrix_UB_13      0.0575649000
_diffrn_orient_matrix_UB_21      -0.0103628000
_diffrn_orient_matrix_UB_22      0.0457242000
_diffrn_orient_matrix_UB_23      -0.1783806000
_diffrn_orient_matrix_UB_31      -0.2558131000
_diffrn_orient_matrix_UB_32      -0.1314362000
_diffrn_orient_matrix_UB_33      -0.1003512000
_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                1452
_reflns_number_total             1561
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.1850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21885(19) 0.11684(14) -0.05591(15) 0.0201(3) Uani 1 1 d . . . . .
H1 H 0.059(5) 0.025(4) -0.139(4) 0.059(7) Uiso 1 1 d . . . . .
O2 O 0.25087(17) 0.63991(14) 0.09142(14) 0.0184(2) Uani 1 1 d . . . . .
O3 O 0.28986(18) 0.77709(13) 0.36568(14) 0.0190(2) Uani 1 1 d . . . . .
N1 N 0.2040(2) 0.18263(16) 0.26961(16) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.2205(2) 0.27648(16) 0.43668(16) 0.0142(3) Uani 1 1 d . . . . .
N3 N 0.2338(2) 0.23166(17) 0.59027(16) 0.0166(3) Uani 1 1 d . . . . .
N4 N 0.2542(2) 0.37862(16) 0.70445(17) 0.0166(3) Uani 1 1 d . . . . .
N5 N 0.2545(2) 0.51552(16) 0.62671(16) 0.0155(3) Uani 1 1 d . . . . .
N6 N 0.1818(2) 0.26957(17) 0.00563(16) 0.0170(3) Uani 1 1 d . . . . .
H6 H 0.218(3) 0.358(3) -0.042(3) 0.032(6) Uiso 1 1 d . . . . .
N7 N 0.2531(2) 0.63644(16) 0.24565(16) 0.0153(3) Uani 1 1 d . . . . .
C1 C 0.2035(2) 0.30811(19) 0.17875(19) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.2214(2) 0.47620(18) 0.28731(19) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.2331(2) 0.44758(19) 0.45719(19) 0.0143(3) Uani 1 1 d . . . . .
O4 O 0.69110(18) 0.15922(14) 0.18825(14) 0.0192(2) Uani 1 1 d . . . . .
H4 H 0.705(4) 0.276(4) 0.254(4) 0.046(7) Uiso 1 1 d . . . . .
N8 N 0.5364(2) 0.02559(17) 0.22769(18) 0.0172(3) Uani 1 1 d . . . . .
H8A H 0.435(4) 0.068(3) 0.254(3) 0.032(5) Uiso 1 1 d . . . . .
H8B H 0.462(4) -0.082(3) 0.126(3) 0.038(6) Uiso 1 1 d . . . . .
H8C H 0.609(4) -0.006(3) 0.323(4) 0.044(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 1.00(3) . ?
O1 N6 1.3880(15) . ?
O2 N7 1.2532(16) . ?
O3 N7 1.2588(16) . ?
N1 N2 1.3864(16) . ?
N1 C1 1.3556(18) . ?
N2 N3 1.3404(17) . ?
N2 C3 1.3401(18) . ?
N3 N4 1.3147(17) . ?
N4 N5 1.3677(17) . ?
N5 C3 1.3319(18) . ?
N6 H6 0.87(2) . ?
N6 C1 1.3326(18) . ?
N7 C2 1.3671(18) . ?
C1 C2 1.4355(19) . ?
C2 C3 1.4183(19) . ?
O4 H4 0.96(3) . ?
O4 N8 1.4141(16) . ?
N8 H8A 0.93(2) . ?
N8 H8B 0.94(2) . ?
N8 H8C 0.89(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 O1 H1 101.5(17) . . ?
C1 N1 N2 101.47(11) . . ?
N3 N2 N1 132.29(12) . . ?
C3 N2 N1 116.60(12) . . ?
C3 N2 N3 111.07(12) . . ?
N4 N3 N2 104.27(11) . . ?
N3 N4 N5 111.86(11) . . ?
C3 N5 N4 105.32(12) . . ?
O1 N6 H6 116.1(14) . . ?
C1 N6 O1 115.34(12) . . ?
C1 N6 H6 120.5(14) . . ?
O2 N7 O3 122.14(12) . . ?
O2 N7 C2 119.05(12) . . ?
O3 N7 C2 118.79(12) . . ?
N1 C1 C2 112.60(12) . . ?
N6 C1 N1 121.17(12) . . ?
N6 C1 C2 126.21(13) . . ?
N7 C2 C1 127.17(13) . . ?
N7 C2 C3 127.52(12) . . ?
C3 C2 C1 104.72(12) . . ?
N2 C3 C2 104.61(12) . . ?
N5 C3 N2 107.48(12) . . ?
N5 C3 C2 147.90(13) . . ?
N8 O4 H4 106.0(14) . . ?
O4 N8 H8A 110.9(13) . . ?
O4 N8 H8B 107.3(14) . . ?
O4 N8 H8C 112.0(15) . . ?
H8A N8 H8B 112.7(19) . . ?
H8A N8 H8C 109(2) . . ?
H8B N8 H8C 105(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.00(3) 1.82(3) 2.8001(16) 166(3) 2 yes
N6 H6 O2 0.87(2) 2.26(2) 2.8069(16) 120.2(18) . yes
N6 H6 N4 0.87(2) 2.19(2) 2.8800(17) 136.0(19) 1_554 yes
O4 H4 N5 0.96(3) 1.68(3) 2.6444(16) 177(2) 2_666 yes
N8 H8A N1 0.93(2) 2.10(2) 3.0206(18) 169.1(19) . yes
N8 H8B O2 0.94(2) 2.16(2) 2.8653(16) 131.4(19) 1_545 yes
N8 H8B O4 0.94(2) 2.28(2) 3.0436(17) 137.6(18) 2_655 yes
N8 H8C O3 0.89(3) 2.59(2) 3.0296(17) 111.0(19) 2_666 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 N6 C1 N1 -15.82(18) . . . . ?
O1 N6 C1 C2 166.18(13) . . . . ?
O2 N7 C2 C1 5.7(2) . . . . ?
O2 N7 C2 C3 175.50(13) . . . . ?
O3 N7 C2 C1 -172.39(13) . . . . ?
O3 N7 C2 C3 -2.6(2) . . . . ?
N1 N2 N3 N4 177.86(13) . . . . ?
N1 N2 C3 N5 -178.25(11) . . . . ?
N1 N2 C3 C2 0.77(16) . . . . ?
N1 C1 C2 N7 171.53(13) . . . . ?
N1 C1 C2 C3 -0.11(15) . . . . ?
N2 N1 C1 N6 -177.74(12) . . . . ?
N2 N1 C1 C2 0.52(14) . . . . ?
N2 N3 N4 N5 -0.07(15) . . . . ?
N3 N2 C3 N5 -0.10(16) . . . . ?
N3 N2 C3 C2 178.91(11) . . . . ?
N3 N4 N5 C3 0.01(15) . . . . ?
N4 N5 C3 N2 0.05(14) . . . . ?
N4 N5 C3 C2 -178.1(2) . . . . ?
N6 C1 C2 N7 -10.3(2) . . . . ?
N6 C1 C2 C3 178.03(13) . . . . ?
N7 C2 C3 N2 -171.97(13) . . . . ?
N7 C2 C3 N5 6.3(3) . . . . ?
C1 N1 N2 N3 -178.47(14) . . . . ?
C1 N1 N2 C3 -0.81(15) . . . . ?
C1 C2 C3 N2 -0.37(14) . . . . ?
C1 C2 C3 N5 177.9(2) . . . . ?
C3 N2 N3 N4 0.11(15) . . . . ?

_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 RVK-0285
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_js224e
_database_code_depnum_ccdc_archive 'CCDC 2338387'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2024-03-07 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;
_audit_creation_date             2024-03-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H2 N7 O2, 2(H2 N0.5)'
_chemical_formula_sum            'C3 H6 N8 O2'
_chemical_formula_weight         186.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         c3h6n8o2
_chemical_oxdiff_usercomment     tvk-0273
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                   9.8448(4)
_cell_length_b                   15.0232(6)
_cell_length_c                   9.6798(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.682(4)
_cell_angle_gamma                90
_cell_volume                     1430.07(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3160
_cell_measurement_theta_min      5.3570
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    1.267
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 9 2 0.0099
0 -9 -2 0.0199
-3 5 -5 0.0500
3 -5 5 0.0077
6 0 -3 0.0422
-6 0 3 0.1052

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.03
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
0.2077 9.1139 2.2171 -0.1403 0.2606 0.9552
-0.2077 -9.1139 -2.2171 0.1403 -0.2606 -0.9552
-2.6521 4.5782 -4.7711 -0.9168 -0.3795 0.1245
2.6413 -4.5044 4.8055 0.9178 0.3799 -0.1151
5.7876 -0.1571 -2.9214 -0.3466 0.8383 -0.4209
-5.7919 0.1200 2.9132 0.3473 -0.8398 0.4172

_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4413
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.615
_diffrn_reflns_theta_min         5.376
_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 0.996
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  89.00   0.50    0.50    --   47.23-125.00 -90.00  102
  2  ω     47.00  95.00   0.50    2.00    --  107.75 -94.00   0.00   96
  3  ω     78.00 103.00   0.50    2.00    --  107.75 -94.00 120.00   50
  4  ω     38.00  65.00   0.50    2.00    --  107.75 -94.00 120.00   54
  5  ω     37.00  65.00   0.50    2.00    --  107.75 -77.00 120.00   56
  6  ω     36.00  62.00   0.50    2.00    --  107.75 -61.00 120.00   52
  7  ω     74.00 100.00   0.50    2.00    --  107.75 -77.00 120.00   52
  8  ω     39.00  68.00   0.50    2.00    --  107.75 -61.00 -60.00   58
  9  ω     38.00  96.00   0.50    2.00    --  107.75 -77.00 -90.00  116
 10  ω     40.00  70.00   0.50    2.00    --  107.75 -77.00-180.00   60
 11  ω     43.00  68.00   0.50    2.00    --  107.75 -61.00-150.00   50
 12  ω     37.00  66.00   0.50    2.00    --  107.75 -61.00 -90.00   58
 13  ω     11.00  37.00   0.50    0.50    --   47.23 -42.00 -99.00   52
 14  ω     36.00  62.00   0.50    2.00    --  107.75 -61.00  60.00   52
 15  ω     35.00  60.00   0.50    2.00    --  107.75 -61.00 150.00   50
 16  ω    -24.00  27.00   0.50    0.50    --   47.23 -19.00 120.00  102
 17  ω     56.00  95.00   0.50    0.50    --   47.23  42.00  52.00   78
 18  ω     97.00 177.00   0.50    2.00    --  107.75  42.00  52.00  160
 19  ω    120.00 176.00   0.50    2.00    --  107.75  30.00   0.00  112
 20  ω    104.00 140.00   0.50    2.00    --  107.75  15.00-180.00   72
 21  ω    -13.00  16.00   0.50    0.50    --  -47.23  42.00  52.00   58
 22  ω    -49.00 -22.00   0.50    2.00    --  -86.25  42.00  52.00   54
 23  ω    -37.00 -12.00   0.50    2.00    --  -86.25  30.00 -90.00   50
 24  ω    -39.00 -11.00   0.50    2.00    --  -86.25  30.00-120.00   56
 25  ω   -118.00 -42.00   0.50    0.50    --  -47.23 -42.00 -99.00  152
 26  ω   -127.00-101.00   0.50    2.00    --  -86.25 -42.00 -99.00   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      0.0091831000
_diffrn_orient_matrix_UB_12      -0.0495384000
_diffrn_orient_matrix_UB_13      0.1395126000
_diffrn_orient_matrix_UB_21      0.1530186000
_diffrn_orient_matrix_UB_22      0.0214424000
_diffrn_orient_matrix_UB_23      0.0150572000
_diffrn_orient_matrix_UB_31      -0.0322560000
_diffrn_orient_matrix_UB_32      0.0871789000
_diffrn_orient_matrix_UB_33      0.0754879000
_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                1245
_reflns_number_total             1465
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.106a 64-bit (release 01-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.063
_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     143
_refine_ls_number_reflns         1465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+0.6753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62658(13) 0.55205(8) 0.49398(12) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.69849(13) 0.50070(7) 0.69718(13) 0.0220(3) Uani 1 1 d . . . . .
N8 N 1.000000 0.54023(14) 0.750000 0.0209(4) Uani 1 2 d S T P . .
N4 N 0.57117(15) 0.85044(9) 0.49780(16) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.64289(14) 0.79274(9) 0.68456(15) 0.0179(3) Uani 1 1 d . . . . .
N6 N 0.73832(16) 0.62902(10) 0.91541(16) 0.0223(4) Uani 1 1 d . . . . .
N9 N 1.000000 0.86137(14) 0.750000 0.0214(5) Uani 1 2 d S T P . .
N3 N 0.61288(14) 0.87142(9) 0.62533(15) 0.0200(3) Uani 1 1 d . . . . .
N7 N 0.65810(14) 0.56430(8) 0.61878(15) 0.0184(3) Uani 1 1 d . . . . .
N5 N 0.57335(14) 0.76083(9) 0.47508(15) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.69081(14) 0.76914(9) 0.81671(15) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.61844(16) 0.72618(10) 0.59524(18) 0.0174(4) Uani 1 1 d . . . . .
C1 C 0.69541(17) 0.67958(11) 0.80813(18) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.65169(17) 0.64800(10) 0.67171(18) 0.0182(4) Uani 1 1 d . . . . .
H9A H 1.025(2) 0.8243(14) 0.824(2) 0.025(5) Uiso 1 1 d . . . . .
H8A H 0.931(3) 0.5027(18) 0.765(3) 0.044(7) Uiso 1 1 d . . . . .
H8B H 1.018(3) 0.5747(16) 0.828(3) 0.036(6) Uiso 1 1 d . . . . .
H6A H 0.759(3) 0.6552(16) 0.994(3) 0.038(7) Uiso 1 1 d . . . . .
H6B H 0.715(2) 0.5744(16) 0.920(2) 0.028(6) Uiso 1 1 d . . . . .
H9B H 0.933(3) 0.8976(19) 0.776(3) 0.052(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N7 1.2468(18) . ?
O2 N7 1.2722(18) . ?
N8 H8A 0.90(3) 2_756 ?
N8 H8A 0.90(3) . ?
N8 H8B 0.92(3) . ?
N8 H8B 0.92(3) 2_756 ?
N4 N3 1.321(2) . ?
N4 N5 1.364(2) . ?
N2 N3 1.3406(18) . ?
N2 N1 1.3885(19) . ?
N2 C3 1.336(2) . ?
N6 C1 1.339(2) . ?
N6 H6A 0.87(3) . ?
N6 H6B 0.85(2) . ?
N9 H9A 0.93(2) 2_756 ?
N9 H9A 0.93(2) . ?
N9 H9B 0.90(3) . ?
N9 H9B 0.90(3) 2_756 ?
N7 C2 1.360(2) . ?
N5 C3 1.331(2) . ?
N1 C1 1.349(2) . ?
C3 C2 1.418(2) . ?
C1 C2 1.449(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
H8A N8 H8A 103(3) . 2_756 ?
H8A N8 H8B 110(2) 2_756 2_756 ?
H8A N8 H8B 110(2) . . ?
H8A N8 H8B 111(2) . 2_756 ?
H8B N8 H8A 111(2) . 2_756 ?
H8B N8 H8B 112(3) . 2_756 ?
N3 N4 N5 112.30(13) . . ?
N3 N2 N1 132.67(14) . . ?
C3 N2 N3 110.71(14) . . ?
C3 N2 N1 116.62(13) . . ?
C1 N6 H6A 118.1(16) . . ?
C1 N6 H6B 120.7(16) . . ?
H6A N6 H6B 116(2) . . ?
H9A N9 H9A 107(3) . 2_756 ?
H9A N9 H9B 108(2) 2_756 2_756 ?
H9A N9 H9B 108(2) . . ?
H9A N9 H9B 114(2) . 2_756 ?
H9B N9 H9A 114(2) . 2_756 ?
H9B N9 H9B 106(4) . 2_756 ?
N4 N3 N2 104.01(12) . . ?
O1 N7 O2 121.59(13) . . ?
O1 N7 C2 119.17(13) . . ?
O2 N7 C2 119.23(14) . . ?
C3 N5 N4 104.60(13) . . ?
C1 N1 N2 102.06(13) . . ?
N2 C3 C2 104.58(14) . . ?
N5 C3 N2 108.38(14) . . ?
N5 C3 C2 147.04(15) . . ?
N6 C1 N1 121.90(15) . . ?
N6 C1 C2 126.18(15) . . ?
N1 C1 C2 111.92(14) . . ?
N7 C2 C3 125.63(15) . . ?
N7 C2 C1 128.95(15) . . ?
C3 C2 C1 104.82(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
N9 H9A N5 0.93(2) 1.98(2) 2.914(2) 176.5(19) 8_566 yes
N8 H8A O2 0.90(3) 2.35(3) 3.0468(13) 134(2) . yes
N8 H8A N3 0.90(3) 2.29(3) 3.041(2) 141(2) 4_646 yes
N8 H8B N4 0.92(3) 2.04(3) 2.9639(18) 176(2) 8_566 yes
N6 H6A N1 0.87(3) 2.19(3) 3.063(2) 176(2) 7_667 yes
N6 H6B O1 0.85(2) 2.22(2) 3.0442(19) 161(2) 6_566 yes
N6 H6B O2 0.85(2) 2.42(2) 2.873(2) 113.6(19) . yes
N9 H9B O2 0.90(3) 2.04(3) 2.9249(19) 166(3) 4_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N7 C2 C3 -3.6(3) . . . . ?
O1 N7 C2 C1 -173.32(16) . . . . ?
O2 N7 C2 C3 175.12(16) . . . . ?
O2 N7 C2 C1 5.4(3) . . . . ?
N4 N5 C3 N2 -0.51(18) . . . . ?
N4 N5 C3 C2 178.8(3) . . . . ?
N2 N1 C1 N6 179.37(16) . . . . ?
N2 N1 C1 C2 0.41(18) . . . . ?
N2 C3 C2 N7 -171.75(16) . . . . ?
N2 C3 C2 C1 0.00(18) . . . . ?
N6 C1 C2 N7 -7.8(3) . . . . ?
N6 C1 C2 C3 -179.18(17) . . . . ?
N3 N4 N5 C3 0.12(18) . . . . ?
N3 N2 N1 C1 178.49(17) . . . . ?
N3 N2 C3 N5 0.7(2) . . . . ?
N3 N2 C3 C2 -178.88(14) . . . . ?
N5 N4 N3 N2 0.31(18) . . . . ?
N5 C3 C2 N7 8.9(4) . . . . ?
N5 C3 C2 C1 -179.3(3) . . . . ?
N1 N2 N3 N4 -179.61(16) . . . . ?
N1 N2 C3 N5 179.90(14) . . . . ?
N1 N2 C3 C2 0.3(2) . . . . ?
N1 C1 C2 N7 171.10(17) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
C3 N2 N3 N4 -0.63(18) . . . . ?
C3 N2 N1 C1 -0.43(19) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id TVK-0260
_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 1.876
_oxdiff_exptl_absorpt_empirical_full_min 0.603
####################################################################### 
# 
# 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_js823a
_database_code_depnum_ccdc_archive 'CCDC 2328920'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2024-01-28 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;
_audit_creation_date             2023-08-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H3 N8 O2, H5 N2'
_chemical_formula_sum            'C3 H8 N10 O2'
_chemical_formula_weight         216.19
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H7N12O4
_chemical_oxdiff_usercomment     TVK-0032
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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   3.7275(3)
_cell_length_b                   6.8786(5)
_cell_length_c                   8.3087(5)
_cell_angle_alpha                107.260(6)
_cell_angle_beta                 93.087(7)
_cell_angle_gamma                94.983(7)
_cell_volume                     201.96(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4919
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.7400
_cell_measurement_theta_min      5.6070
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.667
_exptl_absorpt_coefficient_mu    1.294
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             112
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -4 0 0.0457
0 4 0 0.0286
2 2 1 0.1077
-1 4 0 0.0720
-2 -2 -1 0.1153
-2 1 0 0.1447
0 0 5 0.0064
0 -3 -2 0.0525
0 0 -5 0.0575
0 -1 5 0.0079
0 1 -5 0.0395

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.048
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
-0.0309 -4.1317 -0.3644 -0.0181 -0.0474 -0.9987
0.0508 4.1262 0.3676 0.0153 0.0396 0.9991
1.7867 2.3219 0.5374 -0.2331 -0.6607 0.7135
-0.9285 4.0467 0.1766 0.1495 0.4189 0.8956
-1.8859 -2.0938 -0.5362 0.2479 0.7025 -0.6671
-2.3931 0.8983 -0.3719 0.3338 0.9426 0.0106
-0.2055 0.4660 4.9551 -0.8393 0.2968 0.4554
-0.0280 -3.2129 -2.3599 0.3512 -0.1234 -0.9281
0.2517 0.3150 -5.2486 0.9022 -0.3192 -0.2901
0.2274 -0.6289 5.2537 -0.9596 0.1261 0.2515
-0.2297 0.5260 -5.2297 0.9535 -0.1253 -0.2740

_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  0.0643
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7056
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.241
_diffrn_reflns_theta_min         5.595
_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 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -20.00   0.50    0.11    --  -91.75  45.00-150.00   66
  2  ω    -47.00  26.00   0.50    0.05    --  -46.99  37.00 -30.00  146
  3  ω    -78.00 -19.00   0.50    0.11    --  -91.75  93.00  42.00  118
  4  ω    -77.00  26.00   0.50    0.05    --  -46.99  93.00  42.00  206
  5  ω     16.00  44.00   0.50    0.05    --   30.00  54.00-154.72   56
  6  ω     24.00  50.00   0.50    0.05    --   38.00  51.00 -79.56   52
  7  ω     35.00 120.00   0.50    0.05    --   46.99  37.00-120.00  170
  8  ω    -25.00 119.00   0.50    0.05    --   46.99   0.00-180.00  288
  9  ω    -25.00 119.00   0.50    0.05    --   46.99   0.00-150.00  288
 10  ω    -25.00 119.00   0.50    0.05    --   46.99   0.00-120.00  288
 11  ω    -25.00 119.00   0.50    0.05    --   46.99   0.00 -90.00  288
 12  ω     34.00 119.00   0.50    0.05    --   46.99  45.00 113.61  170
 13  ω    -11.00  77.00   0.50    0.05    --   46.99 -93.00 -69.00  176
 14  ω     44.00 108.00   0.50    0.11    --  113.25-125.00-180.00  128
 15  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00-150.00  124
 16  ω     44.00 108.00   0.50    0.11    --  113.25-125.00 -90.00  128
 17  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00 -30.00  124
 18  ω     42.00 104.00   0.50    0.11    --  113.25 -93.00 -69.00  124
 19  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00  30.00  124
 20  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00 120.00  124
 21  ω     42.00 104.00   0.50    0.11    --  113.25 -94.00 150.00  124
 22  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00 150.00   54
 23  ω     42.00  94.00   0.50    0.11    --  113.25 -77.00  60.00  104
 24  ω     42.00  94.00   0.50    0.11    --  113.25 -77.00 -60.00  104
 25  ω     42.00  94.00   0.50    0.11    --  113.25 -77.00   0.00  104
 26  ω     42.00  94.00   0.50    0.11    --  113.25 -77.00-120.00  104
 27  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00 -90.00   54
 28  ω    -16.00  10.00   0.50    0.05    --   10.00  84.00  71.33   52
 29  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00  60.00   54
 30  ω     42.00  69.00   0.50    0.11    --  113.25 -61.00   0.00   54
 31  ω    106.00 178.00   0.50    0.11    --  113.25  93.00  42.00  144
 32  ω    110.00 178.00   0.50    0.11    --  113.25  77.00  90.00  136
 33  ω    106.00 178.00   0.50    0.11    --  113.25  61.00 120.00  144
 34  ω    101.00 178.00   0.50    0.11    --  113.25  45.00 120.00  154
 35  ω    106.00 178.00   0.50    0.11    --  113.25  61.00  60.00  144
 36  ω    106.00 178.00   0.50    0.11    --  113.25  61.00   0.00  144
 37  ω    101.00 178.00   0.50    0.11    --  113.25  45.00   0.00  154
 38  ω    101.00 178.00   0.50    0.11    --  113.25  45.00 -30.00  154
 39  ω    101.00 178.00   0.50    0.11    --  113.25  45.00  30.00  154
 40  ω    101.00 178.00   0.50    0.11    --  113.25  45.00 -60.00  154
 41  ω    101.00 178.00   0.50    0.11    --  113.25  45.00 -90.00  154
 42  ω    101.00 178.00   0.50    0.11    --  113.25  45.00-120.00  154
 43  ω    101.00 178.00   0.50    0.11    --  113.25  45.00-150.00  154
 44  ω    101.00 178.00   0.50    0.11    --  113.25  30.00-180.00  154
 45  ω    -37.00 -11.00   0.50    0.05    --  -26.00 -58.00 -66.02   52
 46  ω   -117.00 -33.00   0.50    0.05    --  -46.00 -46.00 -35.48  168
 47  ω   -117.00 -33.00   0.50    0.05    --  -46.00 -47.00 -73.76  168
 48  ω   -122.00 -37.00   0.50    0.05    --  -50.00 -42.00-107.59  170
 49  ω   -121.00 -34.00   0.50    0.05    --  -46.99 -19.00  30.00  174
 50  ω   -163.00 -91.00   0.50    0.11    --  -91.75 -49.00  -4.48  144
 51  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -46.00  36.04  168
 52  ω   -134.00 -49.00   0.50    0.05    --  -62.00 -47.00 113.51  170
 53  ω   -142.00 -57.00   0.50    0.05    --  -70.00 -45.00  95.28  170
 54  ω   -134.00 -49.00   0.50    0.05    --  -62.00 -45.00  11.81  170
 55  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -45.00  90.00  168
 56  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -45.00   0.00  168
 57  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -45.00 120.00  168
 58  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -45.00 -30.00  168
 59  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -45.00 -60.00  168
 60  ω   -134.00 -49.00   0.50    0.05    --  -62.00 -46.00-137.30  170
 61  ω   -163.00 -82.00   0.50    0.11    --  -91.75 -47.00-156.98  162
 62  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -45.00-180.00  168
 63  ω   -138.00 -52.00   0.50    0.05    --  -66.00 -44.00-177.81  172
 64  ω   -146.00 -61.00   0.50    0.05    --  -74.00 -42.00-108.98  170
 65  ω   -150.00 -65.00   0.50    0.05    --  -78.00 -42.00 -53.36  170
 66  ω   -142.00 -56.00   0.50    0.05    --  -70.00 -44.00 -37.79  172
 67  ω   -146.00 -61.00   0.50    0.05    --  -74.00 -42.00  55.62  170
 68  ω   -159.00 -73.00   0.50    0.11    --  -86.00 -38.00 143.03  172
 69  ω   -163.00 -79.00   0.50    0.11    --  -91.75 -45.00  60.00  168
 70  ω   -165.00 -79.00   0.50    0.11    --  -91.75 -37.00 -88.87  172
 71  ω   -159.00 -73.00   0.50    0.11    --  -86.00 -38.00-132.46  172
 72  ω   -163.00 -85.00   0.50    0.11    --  -91.75 -93.00 -69.00  156
 73  ω   -163.00-108.00   0.50    0.11    --  -91.75 -94.00-120.00  110
;
_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      -0.1044474000
_diffrn_orient_matrix_UB_12      0.0206429000
_diffrn_orient_matrix_UB_13      -0.1756624000
_diffrn_orient_matrix_UB_21      -0.3964629000
_diffrn_orient_matrix_UB_22      0.0106920000
_diffrn_orient_matrix_UB_23      0.0424464000
_diffrn_orient_matrix_UB_31      0.0723632000
_diffrn_orient_matrix_UB_32      0.2347542000
_diffrn_orient_matrix_UB_33      0.0728340000
_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
_diffrn_special_details          'Refined as an inversion twin.'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.817
_reflns_Friedel_fraction_max     0.742
_reflns_number_gt                1479
_reflns_number_total             1523
_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 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    '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         0.258
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.7(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1523
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.091
_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)+(0.0844P)²+0.1095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1297
_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. Twinned data refinement
 Scales: 0.3(7)
 0.7(7)
;
_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
C1 C -0.8013(10) -0.4121(7) -0.6804(5) 0.0192(9) Uani 1 1 d . . . . .
C2 C -0.6790(11) -0.4110(7) -0.5118(5) 0.0199(9) Uani 1 1 d . . . . .
C3 C -0.5244(10) -0.5989(7) -0.5379(5) 0.0184(8) Uani 1 1 d . . . . .
N1 N -0.7321(9) -0.5821(6) -0.8009(4) 0.0196(8) Uani 1 1 d . . . . .
N2 N -0.5656(8) -0.6865(6) -0.7031(4) 0.0194(7) Uani 1 1 d . . . . .
N3 N -0.4318(9) -0.8689(6) -0.7475(5) 0.0208(8) Uani 1 1 d . . . . .
N4 N -0.3048(10) -0.8859(6) -0.6011(5) 0.0229(8) Uani 1 1 d . . . . .
N5 N -0.3547(9) -0.7223(6) -0.4678(5) 0.0223(8) Uani 1 1 d . . . . .
N6 N -0.9658(10) -0.2661(6) -0.7213(5) 0.0230(8) Uani 1 1 d . . . . .
H6 H -1.02(2) -0.149(14) -0.629(11) 0.043(17) Uiso 1 1 d . . . . .
N7 N -1.0484(11) -0.2894(7) -0.8945(5) 0.0244(8) Uani 1 1 d . . . . .
H7A H -0.929(17) -0.189(11) -0.918(8) 0.032(15) Uiso 1 1 d . . . . .
H7B H -1.271(18) -0.295(11) -0.907(8) 0.036(16) Uiso 1 1 d . . . . .
N8 N -0.7201(9) -0.2689(6) -0.3635(4) 0.0214(8) Uani 1 1 d . . . . .
O1 O -0.8769(8) -0.1153(5) -0.3656(4) 0.0249(7) Uani 1 1 d . . . . .
O2 O -0.6012(9) -0.2943(5) -0.2259(4) 0.0279(8) Uani 1 1 d . . . . .
N9 N 0.0397(9) -0.6863(6) -0.1552(5) 0.0210(8) Uani 1 1 d . . . . .
H9A H -0.047(19) -0.683(11) -0.261(10) 0.047(19) Uiso 1 1 d . . . . .
H9B H 0.069(18) -0.552(12) -0.073(9) 0.042(18) Uiso 1 1 d . . . . .
H9C H 0.268(15) -0.737(10) -0.148(7) 0.027(14) Uiso 1 1 d . . . . .
N10 N -0.2369(9) -0.8150(6) -0.1074(5) 0.0212(7) Uani 1 1 d . . . . .
H10A H -0.186(11) -0.788(7) 0.004(6) 0.004(9) Uiso 1 1 d . . . . .
H10B H -0.209(16) -0.942(11) -0.164(8) 0.029(14) 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
C1 C2 1.447(6) . ?
C1 N1 1.350(6) . ?
C1 N6 1.336(5) . ?
C2 C3 1.424(6) . ?
C2 N8 1.352(6) . ?
C3 N2 1.320(5) . ?
C3 N5 1.344(5) . ?
N1 N2 1.389(4) . ?
N2 N3 1.346(5) . ?
N3 N4 1.323(5) . ?
N4 N5 1.359(6) . ?
N6 H6 0.98(9) . ?
N6 N7 1.414(5) . ?
N7 H7A 0.87(7) . ?
N7 H7B 0.83(7) . ?
N8 O1 1.256(5) . ?
N8 O2 1.270(4) . ?
N9 H9A 0.92(8) . ?
N9 H9B 0.97(8) . ?
N9 H9C 0.95(6) . ?
N9 N10 1.449(5) . ?
N10 H10A 0.90(5) . ?
N10 H10B 0.88(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 112.7(4) . . ?
N6 C1 C2 126.4(4) . . ?
N6 C1 N1 120.8(4) . . ?
C3 C2 C1 104.0(4) . . ?
N8 C2 C1 127.8(4) . . ?
N8 C2 C3 128.1(4) . . ?
N2 C3 C2 104.7(3) . . ?
N2 C3 N5 108.2(4) . . ?
N5 C3 C2 147.1(4) . . ?
C1 N1 N2 100.9(3) . . ?
C3 N2 N1 117.6(3) . . ?
C3 N2 N3 111.5(3) . . ?
N3 N2 N1 130.9(3) . . ?
N4 N3 N2 103.2(3) . . ?
N3 N4 N5 112.8(3) . . ?
C3 N5 N4 104.3(3) . . ?
C1 N6 H6 117(5) . . ?
C1 N6 N7 118.3(4) . . ?
N7 N6 H6 124(5) . . ?
N6 N7 H7A 108(4) . . ?
N6 N7 H7B 106(4) . . ?
H7A N7 H7B 116(6) . . ?
O1 N8 C2 118.9(3) . . ?
O1 N8 O2 121.7(4) . . ?
O2 N8 C2 119.4(4) . . ?
H9A N9 H9B 112(6) . . ?
H9A N9 H9C 117(6) . . ?
H9B N9 H9C 105(5) . . ?
N10 N9 H9A 104(4) . . ?
N10 N9 H9B 109(4) . . ?
N10 N9 H9C 110(3) . . ?
N9 N10 H10A 104(3) . . ?
N9 N10 H10B 106(4) . . ?
H10A N10 H10B 112(5) . . ?

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 H6 N4 0.98(9) 2.14(9) 2.931(5) 137(7) 1_465 yes
N6 H6 O1 0.98(9) 2.16(8) 2.817(5) 123(6) . yes
N9 H9A N5 0.92(8) 1.95(8) 2.848(5) 163(6) . yes
N9 H9B N7 0.97(8) 2.07(8) 2.996(6) 161(6) 1_656 yes
N9 H9C N10 0.95(6) 2.00(6) 2.953(5) 173(6) 1_655 yes
N10 H10A N1 0.90(5) 2.33(5) 3.022(5) 134(4) 1_656 yes
N10 H10B O1 0.88(7) 2.25(7) 2.972(5) 140(5) 1_645 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
C1 C2 C3 N2 -0.2(4) . . . . ?
C1 C2 C3 N5 178.9(6) . . . . ?
C1 C2 N8 O1 -1.1(6) . . . . ?
C1 C2 N8 O2 178.6(4) . . . . ?
C1 N1 N2 C3 -0.4(4) . . . . ?
C1 N1 N2 N3 179.7(4) . . . . ?
C2 C1 N1 N2 0.2(4) . . . . ?
C2 C1 N6 N7 176.7(4) . . . . ?
C2 C3 N2 N1 0.3(4) . . . . ?
C2 C3 N2 N3 -179.7(4) . . . . ?
C2 C3 N5 N4 -179.8(6) . . . . ?
C3 C2 N8 O1 -177.2(4) . . . . ?
C3 C2 N8 O2 2.5(6) . . . . ?
C3 N2 N3 N4 -0.6(4) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
N1 C1 C2 N8 -176.9(4) . . . . ?
N1 C1 N6 N7 -3.2(6) . . . . ?
N1 N2 N3 N4 179.4(4) . . . . ?
N2 C3 N5 N4 -0.7(4) . . . . ?
N2 N3 N4 N5 0.2(5) . . . . ?
N3 N4 N5 C3 0.3(5) . . . . ?
N5 C3 N2 N1 -179.1(3) . . . . ?
N5 C3 N2 N3 0.8(4) . . . . ?
N6 C1 C2 C3 -179.9(4) . . . . ?
N6 C1 C2 N8 3.2(7) . . . . ?
N6 C1 N1 N2 -179.9(4) . . . . ?
N8 C2 C3 N2 176.7(4) . . . . ?
N8 C2 C3 N5 -4.3(10) . . . . ?

# end Validation Reply Form
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id TVK-0032
_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 1.744
_oxdiff_exptl_absorpt_empirical_full_min 0.663
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.3(7)
2 0.7(7)

# start Validation Reply Form
_vrf_PLAT089_js823a              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.09 Note  
RESPONSE: This value is a little low due to the twining in triclinic.
;
