# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_js822b
_database_code_depnum_ccdc_archive 'CCDC 2216920'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H N5 O, H4 N O'
_chemical_formula_sum            'C2 H5 N6 O2'
_chemical_formula_weight         145.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H10O4N12
_chemical_oxdiff_usercomment     JS451
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   3.6274(2)
_cell_length_b                   13.3429(6)
_cell_length_c                   10.8736(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.721(5)
_cell_angle_gamma                90
_cell_volume                     524.49(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2130
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3260
_cell_measurement_theta_min      6.6000
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.654
_exptl_absorpt_coefficient_mu    1.395
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0078
0 0 1 0.0078
1 0 0 0.1743
-1 0 0 0.1563
0 1 0 0.0128
0 -1 0 0.0154

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.016
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
-0.0015 -0.0022 -1.0024 -0.0281 0.1340 0.0395
0.0015 0.0022 1.0024 0.0281 -0.1340 -0.0395
1.0017 -0.0028 0.0115 0.3936 -0.0076 0.1656
-1.0017 0.0028 -0.0115 -0.3936 0.0076 -0.1656
0.0009 0.9995 -0.0003 -0.0426 -0.0386 0.1001
0.0002 -0.9988 -0.0013 0.0429 0.0388 -0.0998

_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  0.0462
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3418
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.488
_diffrn_reflns_theta_min         5.258
_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 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00  96.00   0.50    1.42    --  113.25 -77.00 150.00  100
  2  ω     52.00 101.00   0.50    1.42    --  113.25 -77.00  60.00   98
  3  ω     52.00  97.00   0.50    1.42    --  113.25 -77.00   0.00   90
  4  ω     45.00  70.00   0.50    1.42    --  113.25 -61.00  60.00   50
  5  ω     42.00  67.00   0.50    1.42    --  113.25 -61.00 150.00   50
  6  ω     -5.00  20.00   0.50    0.35    --   47.49 -40.00 -34.00   50
  7  ω     42.00  67.00   0.50    1.42    --  113.25 -61.00-150.00   50
  8  ω    123.00 172.00   0.50    1.42    --  113.25 125.00 -30.00   98
  9  ω    133.00 177.00   0.50    1.42    --  113.25  77.00-180.00   88
 10  ω    137.00 167.00   0.50    1.42    --  113.25  61.00-120.00   60
 11  ω    130.00 178.00   0.50    1.42    --  113.25  61.00 -30.00   96
 12  ω    127.00 175.00   0.50    1.42    --  113.25  45.00 120.00   96
 13  ω    126.00 178.00   0.50    1.42    --  113.25  45.00 150.00  104
 14  ω    115.00 140.00   0.50    1.42    --  113.25  40.00 119.00   50
 15  ω     46.00  80.00   0.50    0.35    --   47.49  40.00 119.00   68
 16  ω     43.00  92.00   0.50    1.42    --  113.25 -94.00 -90.00   98
 17  ω     52.00 104.00   0.50    1.42    --  113.25 -94.00 150.00  104
 18  ω    -64.00 -32.00   0.50    0.35    --  -47.49  77.00 -30.00   64
 19  ω    -46.00 -21.00   0.50    1.42    --  -91.75  40.00 119.00   50
 20  ω    -23.00   4.00   0.50    0.35    --  -47.49  40.00 119.00   54
 21  ω    -20.00  21.00   0.50    0.35    --  -47.49  19.00 -90.00   82
 22  ω    -27.00   0.00   0.50    0.35    --  -47.49  77.00 -30.00   54
 23  ω   -133.00 -91.00   0.50    1.42    --  -91.75 -40.00 -34.00   84
 24  ω   -119.00 -79.00   0.50    0.35    --  -47.49 -40.00 -34.00   80
 25  ω    -76.00 -34.00   0.50    0.35    --  -47.49 -40.00 -34.00   84
 26  ω   -158.00-128.00   0.50    1.42    --  -91.75 -77.00 150.00   60
 27  ω   -163.00-138.00   0.50    1.42    --  -91.75 -77.00  90.00   50
 28  ω   -163.00-138.00   0.50    1.42    --  -91.75 -61.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3925188000
_diffrn_orient_matrix_UB_12      -0.0429131000
_diffrn_orient_matrix_UB_13      0.0275153000
_diffrn_orient_matrix_UB_21      -0.0061979000
_diffrn_orient_matrix_UB_22      -0.0386773000
_diffrn_orient_matrix_UB_23      -0.1336151000
_diffrn_orient_matrix_UB_31      0.1660879000
_diffrn_orient_matrix_UB_32      0.0999728000
_diffrn_orient_matrix_UB_33      -0.0398656000
_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                988
_reflns_number_total             1100
_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 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.095
_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)+(0.0835P)²+0.1732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1336
_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 0.2439(4) 0.83912(10) 0.34710(12) 0.0208(4) Uani 1 1 d . . . . .
H1 H 0.324(8) 0.782(2) 0.369(3) 0.030(7) Uiso 1 1 d . . . . .
N1 N 0.1635(4) 0.88357(11) 0.45603(14) 0.0172(4) Uani 1 1 d . . . . .
N2 N -0.1562(4) 0.99083(11) 0.21751(14) 0.0173(4) Uani 1 1 d . . . . .
N3 N -0.1310(4) 1.06455(11) 0.13445(14) 0.0180(4) Uani 1 1 d . . . . .
N4 N 0.0378(4) 1.14241(11) 0.18746(14) 0.0180(4) Uani 1 1 d . . . . .
N5 N 0.1224(4) 1.12205(11) 0.30667(14) 0.0168(4) Uani 1 1 d . . . . .
C1 C 0.0438(5) 0.97452(13) 0.44249(15) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.0001(5) 1.02827(12) 0.32303(16) 0.0155(4) Uani 1 1 d . . . . .
O2 O 0.0928(3) 0.77145(9) 0.06798(12) 0.0183(3) Uani 1 1 d . . . . .
H2 H 0.181(9) 0.714(3) 0.113(3) 0.048(9) Uiso 1 1 d . . . . .
N6 N 0.3713(4) 0.84476(11) 0.09287(15) 0.0176(4) Uani 1 1 d . . . . .
H6A H 0.347(7) 0.892(2) 0.031(2) 0.022(6) Uiso 1 1 d . . . . .
H6B H 0.359(7) 0.8743(19) 0.164(3) 0.023(6) Uiso 1 1 d . . . . .
H6C H 0.597(8) 0.817(2) 0.085(2) 0.024(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 0.84(3) . ?
O1 N1 1.3772(19) . ?
N1 C1 1.293(2) . ?
N2 N3 1.344(2) . ?
N2 C2 1.334(2) . ?
N3 N4 1.315(2) . ?
N4 N5 1.335(2) . ?
N5 C2 1.344(2) . ?
C1 C1 1.481(3) 3_576 ?
C1 C2 1.481(2) . ?
O2 H2 0.95(4) . ?
O2 N6 1.4160(19) . ?
N6 H6A 0.92(3) . ?
N6 H6B 0.88(3) . ?
N6 H6C 0.91(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
N1 O1 H1 104(2) . . ?
C1 N1 O1 113.52(14) . . ?
C2 N2 N3 104.85(14) . . ?
N4 N3 N2 109.80(14) . . ?
N3 N4 N5 109.06(14) . . ?
N4 N5 C2 105.42(14) . . ?
N1 C1 C1 115.35(19) . 3_576 ?
N1 C1 C2 124.40(15) . . ?
C2 C1 C1 120.23(19) . 3_576 ?
N2 C2 N5 110.86(15) . . ?
N2 C2 C1 125.47(15) . . ?
N5 C2 C1 123.65(15) . . ?
N6 O2 H2 105(2) . . ?
O2 N6 H6A 108.1(16) . . ?
O2 N6 H6B 113.2(18) . . ?
O2 N6 H6C 109.5(16) . . ?
H6A N6 H6B 109(2) . . ?
H6A N6 H6C 104(2) . . ?
H6B N6 H6C 112(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 N4 0.84(3) 2.04(3) 2.7761(19) 146(3) 2_545 yes
O1 H1 O2 0.84(3) 2.41(3) 3.0078(18) 129(2) 4_676 yes
O2 H2 N5 0.95(4) 1.64(4) 2.582(2) 174(3) 2_545 yes
N6 H6A N3 0.92(3) 1.99(3) 2.825(2) 150(2) 3_575 yes
N6 H6B O1 0.88(3) 2.12(3) 2.841(2) 140(2) . yes
N6 H6B N2 0.88(3) 2.38(3) 2.862(2) 115(2) 1_655 yes
N6 H6C O2 0.91(3) 1.92(3) 2.828(2) 174(2) 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C1 -179.61(18) . . . 3_576 ?
O1 N1 C1 C2 -0.9(2) . . . . ?
N1 C1 C2 N2 46.0(3) . . . . ?
N1 C1 C2 N5 -132.52(19) . . . . ?
N2 N3 N4 N5 -0.84(19) . . . . ?
N3 N2 C2 N5 -0.52(19) . . . . ?
N3 N2 C2 C1 -179.23(15) . . . . ?
N3 N4 N5 C2 0.49(19) . . . . ?
N4 N5 C2 N2 0.03(19) . . . . ?
N4 N5 C2 C1 178.77(15) . . . . ?
C1 C1 C2 N2 -135.3(2) 3_576 . . . ?
C1 C1 C2 N5 46.1(3) 3_576 . . . ?
C2 N2 N3 N4 0.83(18) . . . . ?

_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 JS451
_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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.674
####################################################################### 
# 
# 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_js722g
_database_code_depnum_ccdc_archive 'CCDC 2216922'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2022-10-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_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 N10 O2'
_chemical_formula_sum            'C4 H2 N10 O2'
_chemical_formula_weight         222.16
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H4N10O4
_chemical_oxdiff_usercomment     JS435
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.9741(3)
_cell_length_b                   9.6391(4)
_cell_length_c                   14.2140(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     818.51(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2814
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.2560
_cell_measurement_theta_min      5.5310
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0055
0 0 1 0.0095
-1 -1 0 0.0749
1 1 0 0.0749
1 -1 1 0.0465
-1 1 -1 0.0655
-2 -5 -4 0.0588
0 5 1 0.0443

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.015
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
0.0066 0.0149 -1.0370 0.0224 0.0966 0.0532
-0.0066 -0.0149 1.0370 -0.0224 -0.0966 -0.0532
-0.9814 -0.9754 -0.1464 -0.0493 -0.1248 0.2656
0.9814 0.9754 0.1464 0.0493 0.1248 -0.2656
0.9963 -1.0058 1.0232 -0.2595 0.0354 -0.1887
-0.9963 1.0058 -1.0232 0.2595 -0.0354 0.1887
-1.9109 -4.8557 -3.6441 -0.4610 0.0509 0.8859
-0.0602 4.9009 1.4376 0.6935 -0.1145 -0.3784

_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  0.0603
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5184
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.724
_diffrn_reflns_theta_min         5.545
_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 0.997
_diffrn_measured_fraction_theta_max 0.984
_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  24.00   0.50    0.86    --  -47.62  50.00-161.00  124
  2  ω     24.00  49.00   0.50    0.86    --   47.62 -50.00  51.00   50
  3  ω     76.00 101.00   0.50    0.86    --   47.62  50.00-161.00   50
  4  ω   -145.00-119.00   0.50    3.43    --  -91.75 -50.00  51.00   52
  5  ω    -58.00 -33.00   0.50    3.43    --  -91.75  50.00-161.00   50
  6  ω    151.00 178.00   0.50    3.43    --  113.25  50.00-161.00   54
  7  ω    101.00 147.00   0.50    3.43    --  113.25  50.00-161.00   92
  8  ω    -15.00  28.00   0.50    0.86    --  -47.62  19.00 -30.00   86
  9  ω   -119.00 -39.00   0.50    0.86    --  -47.62 -50.00  51.00  160
 10  ω    -26.00  25.00   0.50    0.86    --   47.62 -19.00 -90.00  102
 11  ω   -161.00-135.00   0.50    3.43    --  -91.75 -94.00 150.00   52
 12  ω   -161.00-132.00   0.50    3.43    --  -91.75 -77.00-150.00   58
 13  ω    131.00 158.00   0.50    3.43    --  113.25  77.00 -60.00   54
 14  ω     42.00  67.00   0.50    3.43    --  113.25 -61.00-180.00   50
 15  ω     42.00  68.00   0.50    3.43    --  113.25 -77.00  60.00   52
 16  ω    105.00 130.00   0.50    3.43    --  113.25  30.00 -60.00   50
 17  ω     42.00  67.00   0.50    3.43    --  113.25 -61.00 120.00   50
 18  ω    131.00 172.00   0.50    3.43    --  113.25  30.00 -60.00   82
 19  ω     46.00  79.00   0.50    3.43    --  113.25 -94.00-120.00   66
 20  ω     42.00  67.00   0.50    3.43    --  113.25 -61.00 -60.00   50
 21  ω    101.00 175.00   0.50    3.43    --  113.25  15.00 -90.00  148
 22  ω     45.00  70.00   0.50    3.43    --  113.25 -61.00 -90.00   50
 23  ω     57.00  90.00   0.50    3.43    --  113.25 -77.00  90.00   66
 24  ω     44.00  70.00   0.50    3.43    --  113.25 -61.00   0.00   52
 25  ω     43.00  68.00   0.50    3.43    --  113.25 -61.00  60.00   50
 26  ω     65.00 101.00   0.50    3.43    --  113.25 -77.00 -60.00   72
 27  ω     62.00 100.00   0.50    3.43    --  113.25 -94.00-150.00   76
 28  ω     80.00 105.00   0.50    3.43    --  113.25 -77.00  60.00   50
 29  ω     42.00  67.00   0.50    3.43    --  113.25 -61.00 150.00   50
 30  ω     42.00  67.00   0.50    3.43    --  113.25 -61.00 -30.00   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      -0.0921653013
_diffrn_orient_matrix_UB_12      0.1462644634
_diffrn_orient_matrix_UB_13      -0.0200611419
_diffrn_orient_matrix_UB_21      0.1356081885
_diffrn_orient_matrix_UB_22      0.0053369039
_diffrn_orient_matrix_UB_23      -0.0921759410
_diffrn_orient_matrix_UB_31      -0.1990470740
_diffrn_orient_matrix_UB_32      -0.0639723063
_diffrn_orient_matrix_UB_33      -0.0534886801
_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         0.605
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                1560
_reflns_number_total             1677
_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 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.093
_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)+(0.0876P)²+0.3384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1446
_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 0.6916(5) 0.5937(3) 0.1272(2) 0.0302(7) Uani 1 1 d . . . . .
O2 O 0.4219(5) 0.4563(3) 0.19001(19) 0.0299(7) Uani 1 1 d . . . . .
N1 N 0.4917(6) 0.5114(3) 0.1187(2) 0.0266(7) Uani 1 1 d . . . . .
N2 N 0.7380(6) 0.6483(3) 0.0410(2) 0.0285(7) Uani 1 1 d . . . . .
N3 N 0.0766(6) 0.3912(3) 0.0583(2) 0.0254(7) Uani 1 1 d . . . . .
N4 N -0.0878(6) 0.3398(3) 0.0028(3) 0.0289(7) Uani 1 1 d . . . . .
N5 N -0.0480(6) 0.3635(3) -0.0848(2) 0.0297(7) Uani 1 1 d . . . . .
N6 N 0.1487(6) 0.4330(4) -0.0871(2) 0.0272(7) Uani 1 1 d . . . . .
N7 N 0.7222(6) 0.7469(3) -0.1502(2) 0.0303(7) Uani 1 1 d . . . . .
N8 N 0.6767(5) 0.7530(3) -0.2406(2) 0.0311(8) Uani 1 1 d . . . . .
N9 N 0.5221(6) 0.6581(3) -0.2568(2) 0.0278(7) Uani 1 1 d . . . . .
N10 N 0.4642(6) 0.5866(3) -0.1812(2) 0.0280(7) Uani 1 1 d . . . . .
C1 C 0.4300(6) 0.5171(4) 0.0298(3) 0.0249(8) Uani 1 1 d . . . . .
C2 C 0.5851(6) 0.6035(4) -0.0173(3) 0.0251(8) Uani 1 1 d . . . . .
C3 C 0.2218(7) 0.4498(4) 0.0003(3) 0.0243(7) Uani 1 1 d . . . . .
C4 C 0.5921(6) 0.6443(4) -0.1157(3) 0.0248(8) Uani 1 1 d . . . . .
H6 H 0.200(9) 0.455(5) -0.143(3) 0.025(11) Uiso 1 1 d . . . . .
H9 H 0.471(9) 0.637(6) -0.319(4) 0.033(13) 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 N1 1.438(4) . ?
O1 N2 1.362(4) . ?
O2 N1 1.218(4) . ?
N1 C1 1.318(5) . ?
N2 C2 1.307(5) . ?
N3 N4 1.354(5) . ?
N3 C3 1.323(5) . ?
N4 N5 1.289(5) . ?
N5 N6 1.353(5) . ?
N6 C3 1.327(5) . ?
N6 H6 0.88(5) . ?
N7 N8 1.315(5) . ?
N7 C4 1.349(5) . ?
N8 N9 1.321(4) . ?
N9 N10 1.323(5) . ?
N9 H9 0.96(5) . ?
N10 C4 1.327(5) . ?
C1 C2 1.414(5) . ?
C1 C3 1.464(5) . ?
C2 C4 1.454(5) . ?

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 O1 N1 107.9(3) . . ?
O2 N1 O1 117.1(3) . . ?
O2 N1 C1 136.1(4) . . ?
C1 N1 O1 106.8(3) . . ?
C2 N2 O1 107.5(3) . . ?
C3 N3 N4 105.6(3) . . ?
N5 N4 N3 111.4(3) . . ?
N4 N5 N6 105.8(3) . . ?
N5 N6 H6 116(3) . . ?
C3 N6 N5 108.9(3) . . ?
C3 N6 H6 135(3) . . ?
N8 N7 C4 105.6(3) . . ?
N7 N8 N9 106.5(3) . . ?
N8 N9 N10 113.7(3) . . ?
N8 N9 H9 122(3) . . ?
N10 N9 H9 124(3) . . ?
N9 N10 C4 101.6(3) . . ?
N1 C1 C2 107.2(3) . . ?
N1 C1 C3 119.6(3) . . ?
C2 C1 C3 133.0(4) . . ?
N2 C2 C1 110.6(3) . . ?
N2 C2 C4 120.1(3) . . ?
C1 C2 C4 129.3(3) . . ?
N3 C3 N6 108.4(3) . . ?
N3 C3 C1 124.6(3) . . ?
N6 C3 C1 127.0(3) . . ?
N7 C4 C2 124.3(3) . . ?
N10 C4 N7 112.6(4) . . ?
N10 C4 C2 123.0(4) . . ?

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 N10 0.88(5) 2.10(5) 2.745(5) 130(4) . yes
N9 H9 N3 0.96(5) 1.79(5) 2.734(5) 170(5) 2_564 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 -1.1(4) . . . . ?
O1 N1 C1 C3 -176.2(3) . . . . ?
O1 N2 C2 C1 0.3(4) . . . . ?
O1 N2 C2 C4 -179.6(3) . . . . ?
O2 N1 C1 C2 178.8(4) . . . . ?
O2 N1 C1 C3 3.7(6) . . . . ?
N1 O1 N2 C2 -1.0(4) . . . . ?
N1 C1 C2 N2 0.5(4) . . . . ?
N1 C1 C2 C4 -179.6(4) . . . . ?
N1 C1 C3 N3 5.8(5) . . . . ?
N1 C1 C3 N6 -172.1(4) . . . . ?
N2 O1 N1 O2 -178.6(3) . . . . ?
N2 O1 N1 C1 1.3(4) . . . . ?
N2 C2 C4 N7 -12.8(6) . . . . ?
N2 C2 C4 N10 169.3(4) . . . . ?
N3 N4 N5 N6 -0.1(4) . . . . ?
N4 N3 C3 N6 -0.6(4) . . . . ?
N4 N3 C3 C1 -178.9(3) . . . . ?
N4 N5 N6 C3 -0.3(4) . . . . ?
N5 N6 C3 N3 0.6(4) . . . . ?
N5 N6 C3 C1 178.8(3) . . . . ?
N7 N8 N9 N10 -1.1(4) . . . . ?
N8 N7 C4 N10 -0.7(5) . . . . ?
N8 N7 C4 C2 -178.7(3) . . . . ?
N8 N9 N10 C4 0.6(4) . . . . ?
N9 N10 C4 N7 0.0(4) . . . . ?
N9 N10 C4 C2 178.1(3) . . . . ?
C1 C2 C4 N7 167.3(4) . . . . ?
C1 C2 C4 N10 -10.6(6) . . . . ?
C2 C1 C3 N3 -167.8(4) . . . . ?
C2 C1 C3 N6 14.3(6) . . . . ?
C3 N3 N4 N5 0.4(4) . . . . ?
C3 C1 C2 N2 174.7(4) . . . . ?
C3 C1 C2 C4 -5.4(7) . . . . ?
C4 N7 N8 N9 1.0(4) . . . . ?

_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 JS435
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_js822c
_database_code_depnum_ccdc_archive 'CCDC 2216921'
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2022-08-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H7 N8, C2 H N5 O'
_chemical_formula_sum            'C5 H8 N13 O'
_chemical_formula_weight         266.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H16N26O2
_chemical_oxdiff_usercomment     JS457
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                   12.3231(3)
_cell_length_b                   7.9468(2)
_cell_length_c                   20.7961(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.465(2)
_cell_angle_gamma                90
_cell_volume                     2023.60(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3544
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.1600
_cell_measurement_theta_min      4.2740
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0067
0 0 1 0.0047
-1 0 0 0.0288
1 0 0 0.0288
-1 -1 1 0.0325
1 1 -1 0.0325
-1 1 -1 0.0271
1 -1 1 0.0271

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.011
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 0.0002 -0.9998 0.0726 0.0126 0.0114
0.0000 -0.0002 0.9998 -0.0726 -0.0126 -0.0114
-1.0001 0.0002 0.0012 -0.0077 0.0148 0.1247
1.0001 -0.0002 -0.0012 0.0077 -0.0148 -0.1247
-1.0002 -1.0000 1.0006 -0.1095 0.1923 0.0890
1.0002 1.0000 -1.0006 0.1095 -0.1923 -0.0890
-1.0000 1.0005 -0.9983 0.0942 -0.1628 0.1604
1.0000 -1.0005 0.9983 -0.0942 0.1628 -0.1604

_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6800
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.879
_diffrn_reflns_theta_min         4.279
_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 0.990
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -87.00   0.50    9.30    --  -46.69-155.00 -99.00   60
  2  ω    -46.00 -12.00   0.50    9.30    --  -46.69 119.00 141.00   68
  3  ω    -80.00 -55.00   0.50    9.30    --  -46.69-155.00 -99.00   50
  4  ω     55.00  81.00   0.50    9.30    --   46.69-119.00  56.00   52
  5  ω   -116.00 -79.00   0.50   37.22    --  -91.75-119.00  56.00   74
  6  ω   -100.00 -73.00   0.50   37.22    --  -91.75-155.00 -99.00   54
  7  ω    103.00 129.00   0.50   37.22    --  113.25-155.00 -99.00   52
  8  ω     54.00 100.00   0.50   37.22    --  113.25-155.00 -99.00   92
  9  ω     71.00 101.00   0.50   37.22    --  113.25-119.00  56.00   60
 10  ω    -10.00  26.00   0.50    9.30    --  -46.69  37.00 -90.00   72
 11  ω    -41.00 -15.00   0.50    9.30    --  -46.69  37.00 -90.00   52
 12  ω    -24.00  29.00   0.50    9.30    --  -46.69  19.00-180.00  106
 13  ω     71.00 110.00   0.50    9.30    --   46.69-155.00 -99.00   78
 14  ω    -23.00  25.00   0.50    9.30    --   46.69 -19.00 -60.00   96
 15  ω    -48.00 -21.00   0.50   37.22    --  -91.75  45.00 -60.00   54
 16  ω   -160.00-130.00   0.50   37.22    --  -91.75 -45.00 150.00   60
 17  ω    -52.00 -27.00   0.50   37.22    --  -91.75  45.00   0.00   50
 18  ω     43.00  70.00   0.50   37.22    --  113.25 -61.00  30.00   54
 19  ω    147.00 172.00   0.50   37.22    --  113.25  61.00-180.00   50
 20  ω    127.00 172.00   0.50   37.22    --  113.25  77.00   0.00   90
 21  ω    101.00 138.00   0.50   37.22    --  113.25  30.00-120.00   74
 22  ω    150.00 178.00   0.50   37.22    --  113.25  30.00-120.00   56
 23  ω     42.00  70.00   0.50   37.22    --  113.25 -61.00 -30.00   56
 24  ω    133.00 161.00   0.50   37.22    --  113.25  77.00  90.00   56
 25  ω     44.00  70.00   0.50   37.22    --  113.25 -61.00 -60.00   52
 26  ω     42.00  67.00   0.50   37.22    --  113.25 -61.00  60.00   50
 27  ω     55.00 104.00   0.50   37.22    --  113.25 -94.00  90.00   98
 28  ω     58.00 103.00   0.50   37.22    --  113.25 -94.00  30.00   90
 29  ω    113.00 153.00   0.50   37.22    --  113.25 125.00   0.00   80
 30  ω     45.00  72.00   0.50   37.22    --  113.25 -77.00 -90.00   54
 31  ω     80.00 105.00   0.50   37.22    --  113.25 -77.00 -90.00   50
 32  ω     61.00  89.00   0.50   37.22    --  113.25 -94.00-150.00   56
 33  ω     42.00  67.00   0.50   37.22    --  113.25 -61.00-120.00   50
 34  ω     64.00  99.00   0.50   37.22    --  113.25 -94.00 120.00   70
 35  ω    115.00 147.00   0.50   37.22    --  113.25 119.00 141.00   64
;
_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      0.0076033000
_diffrn_orient_matrix_UB_12      0.0292918000
_diffrn_orient_matrix_UB_13      -0.0725850000
_diffrn_orient_matrix_UB_21      -0.0148232000
_diffrn_orient_matrix_UB_22      -0.1901184000
_diffrn_orient_matrix_UB_23      -0.0126452000
_diffrn_orient_matrix_UB_31      -0.1246808000
_diffrn_orient_matrix_UB_32      0.0243635000
_diffrn_orient_matrix_UB_33      -0.0113838000
_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                1880
_reflns_number_total             2097
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.124
_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)+(0.0406P)²+3.9387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1063
_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
N6 N 0.35880(13) 0.1335(2) 0.52590(8) 0.0230(4) Uani 1 1 d . . . . .
N7 N 0.45462(13) 0.1975(2) 0.50396(8) 0.0222(4) Uani 1 1 d . . . . .
N8 N 0.45593(13) 0.2971(2) 0.59846(8) 0.0194(3) Uani 1 1 d . . . . .
N9 N 0.46437(13) 0.3670(2) 0.66034(7) 0.0202(3) Uani 1 1 d . . . . .
N10 N 0.31162(13) 0.2085(2) 0.63744(8) 0.0205(3) Uani 1 1 d . . . . .
N11 N 0.21643(14) 0.1205(2) 0.64693(9) 0.0236(4) Uani 1 1 d . . . . .
N12 N 0.60466(14) 0.3801(2) 0.54099(9) 0.0244(4) Uani 1 1 d . . . . .
N13 N 0.34353(14) 0.3433(2) 0.74003(8) 0.0202(4) Uani 1 1 d . . . . .
C3 C 0.36605(15) 0.1998(2) 0.58325(9) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.51285(15) 0.2970(2) 0.54703(9) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.37412(15) 0.3087(2) 0.68214(9) 0.0190(4) Uani 1 1 d . . . . .
O1 O -0.10786(11) 0.47651(18) 0.86419(7) 0.0212(3) Uani 1 1 d . . . . .
N1 N -0.09232(12) 0.4828(2) 0.79894(8) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.16199(12) 0.2389(2) 0.81026(8) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.21098(12) 0.1632(2) 0.86318(8) 0.0192(3) Uani 1 1 d . . . . .
N4 N 0.15204(13) 0.1814(2) 0.91167(8) 0.0210(4) Uani 1 1 d . . . . .
N5 N 0.06249(13) 0.2706(2) 0.89179(8) 0.0200(4) Uani 1 1 d . . . . .
C1 C -0.00808(14) 0.4004(2) 0.78526(9) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.07024(14) 0.3050(2) 0.82931(9) 0.0162(4) Uani 1 1 d . . . . .
H11A H 0.160(2) 0.196(4) 0.6495(13) 0.038(7) Uiso 1 1 d . . . . .
H13A H 0.397(2) 0.367(3) 0.7693(12) 0.021(6) Uiso 1 1 d . . . . .
H12A H 0.642(2) 0.370(4) 0.5031(15) 0.048(8) Uiso 1 1 d . . . . .
H12B H 0.639(2) 0.443(4) 0.5760(15) 0.049(8) Uiso 1 1 d . . . . .
H11B H 0.223(2) 0.072(4) 0.6874(15) 0.047(8) Uiso 1 1 d . . . . .
H1 H -0.171(3) 0.545(4) 0.8647(15) 0.060(9) Uiso 1 1 d . . . . .
H13B H 0.284(2) 0.292(4) 0.7505(14) 0.045(8) Uiso 1 1 d . . . . .
H7 H 0.465(3) 0.171(4) 0.4624(17) 0.060(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N6 N7 1.408(2) . ?
N6 C3 1.298(3) . ?
N7 C4 1.341(3) . ?
N7 H7 0.91(3) . ?
N8 N9 1.395(2) . ?
N8 C3 1.358(3) . ?
N8 C4 1.343(2) . ?
N9 C5 1.331(2) . ?
N10 N11 1.398(2) . ?
N10 C3 1.377(2) . ?
N10 C5 1.389(3) . ?
N11 H11A 0.93(3) . ?
N11 H11B 0.92(3) . ?
N12 C4 1.328(3) . ?
N12 H12A 0.96(3) . ?
N12 H12B 0.95(3) . ?
N13 C5 1.330(2) . ?
N13 H13A 0.87(3) . ?
N13 H13B 0.89(3) . ?
O1 N1 1.392(2) . ?
O1 H1 0.95(3) . ?
N1 C1 1.286(2) . ?
N2 N3 1.337(2) . ?
N2 C2 1.346(2) . ?
N3 N4 1.315(2) . ?
N4 N5 1.337(2) . ?
N5 C2 1.342(2) . ?
C1 C1 1.502(4) 2_556 ?
C1 C2 1.465(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
C3 N6 N7 100.24(16) . . ?
N6 N7 H7 116(2) . . ?
C4 N7 N6 113.68(16) . . ?
C4 N7 H7 130(2) . . ?
C3 N8 N9 114.56(15) . . ?
C4 N8 N9 138.02(17) . . ?
C4 N8 C3 107.42(16) . . ?
C5 N9 N8 101.37(15) . . ?
C3 N10 N11 125.78(16) . . ?
C3 N10 C5 106.96(15) . . ?
C5 N10 N11 127.05(16) . . ?
N10 N11 H11A 109.5(17) . . ?
N10 N11 H11B 110.7(18) . . ?
H11A N11 H11B 102(2) . . ?
C4 N12 H12A 121.5(18) . . ?
C4 N12 H12B 120.4(18) . . ?
H12A N12 H12B 118(2) . . ?
C5 N13 H13A 114.3(16) . . ?
C5 N13 H13B 117.0(19) . . ?
H13A N13 H13B 121(2) . . ?
N6 C3 N8 114.52(17) . . ?
N6 C3 N10 141.54(18) . . ?
N8 C3 N10 103.94(16) . . ?
N7 C4 N8 104.13(16) . . ?
N12 C4 N7 128.86(18) . . ?
N12 C4 N8 127.00(18) . . ?
N9 C5 N10 113.16(17) . . ?
N13 C5 N9 124.70(18) . . ?
N13 C5 N10 122.13(17) . . ?
N1 O1 H1 101.1(19) . . ?
C1 N1 O1 113.60(15) . . ?
N3 N2 C2 104.47(15) . . ?
N4 N3 N2 110.15(14) . . ?
N3 N4 N5 109.21(15) . . ?
N4 N5 C2 105.15(15) . . ?
N1 C1 C1 114.52(17) . 2_556 ?
N1 C1 C2 128.05(17) . . ?
C2 C1 C1 117.41(16) . 2_556 ?
N2 C2 C1 122.28(16) . . ?
N5 C2 N2 111.03(16) . . ?
N5 C2 C1 126.69(16) . . ?

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
N6 N7 C4 N8 0.9(2) . . . . ?
N6 N7 C4 N12 -177.99(19) . . . . ?
N7 N6 C3 N8 0.0(2) . . . . ?
N7 N6 C3 N10 179.4(2) . . . . ?
N8 N9 C5 N10 -0.1(2) . . . . ?
N8 N9 C5 N13 -178.86(17) . . . . ?
N9 N8 C3 N6 -179.38(16) . . . . ?
N9 N8 C3 N10 1.0(2) . . . . ?
N9 N8 C4 N7 179.1(2) . . . . ?
N9 N8 C4 N12 -2.0(4) . . . . ?
N11 N10 C3 N6 4.5(4) . . . . ?
N11 N10 C3 N8 -176.08(17) . . . . ?
N11 N10 C5 N9 175.74(17) . . . . ?
N11 N10 C5 N13 -5.5(3) . . . . ?
C3 N6 N7 C4 -0.6(2) . . . . ?
C3 N8 N9 C5 -0.6(2) . . . . ?
C3 N8 C4 N7 -0.8(2) . . . . ?
C3 N8 C4 N12 178.07(19) . . . . ?
C3 N10 C5 N9 0.8(2) . . . . ?
C3 N10 C5 N13 179.51(17) . . . . ?
C4 N8 N9 C5 179.5(2) . . . . ?
C4 N8 C3 N6 0.6(2) . . . . ?
C4 N8 C3 N10 -179.05(15) . . . . ?
C5 N10 C3 N6 179.6(2) . . . . ?
C5 N10 C3 N8 -1.0(2) . . . . ?
O1 N1 C1 C1 177.96(12) . . . 2_556 ?
O1 N1 C1 C2 -0.2(3) . . . . ?
N1 C1 C2 N2 -172.68(18) . . . . ?
N1 C1 C2 N5 7.6(3) . . . . ?
N2 N3 N4 N5 -0.2(2) . . . . ?
N3 N2 C2 N5 -0.4(2) . . . . ?
N3 N2 C2 C1 179.91(16) . . . . ?
N3 N4 N5 C2 0.0(2) . . . . ?
N4 N5 C2 N2 0.2(2) . . . . ?
N4 N5 C2 C1 179.95(17) . . . . ?
C1 C1 C2 N2 9.2(2) 2_556 . . . ?
C1 C1 C2 N5 -170.53(16) 2_556 . . . ?
C2 N2 N3 N4 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 JS457
_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.910
