# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_js9325d
_database_code_depnum_ccdc_archive 'CCDC 2491019'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2025-12-10 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
_audit_creation_date             2025-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H6 N8'
_chemical_formula_sum            'C3 H6 N8'
_chemical_formula_weight         154.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H16N2O6
_chemical_oxdiff_usercomment     JS1515
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'

_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 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2311(2)
_cell_length_b                   13.5439(3)
_cell_length_c                   6.9938(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.974(4)
_cell_angle_gamma                90
_cell_volume                     610.44(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2511
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6010
_cell_measurement_theta_min      6.5320
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    1.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (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            'dark red'
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 0 0.0659
2 1 0 0.0879
1 -1 -2 0.0609
-1 1 2 0.0508
0 1 0 0.0115
0 -1 0 0.0205

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.032
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 -1.0000 0.0000 0.4248 -0.2251 0.1020
2.0000 1.0000 -0.0000 -0.4248 0.2251 -0.1020
1.0000 -1.0000 -2.0000 0.0035 -0.2043 -0.4066
-1.0000 1.0000 2.0000 -0.0035 0.2043 0.4066
-0.0000 1.0000 0.0000 -0.0762 -0.0588 0.0607
0.0000 -1.0000 -0.0000 0.0762 0.0588 -0.0607

_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4048
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.875
_diffrn_reflns_theta_min         6.537
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00   5.00   0.50    0.13    --  -47.65  78.00 100.00   54
  2  ω    -51.00 -26.00   0.50    0.13    --  -47.65  78.00 100.00   50
  3  ω    -30.00  26.00   0.50    0.13    --  -47.65  19.00  90.00  112
  4  ω    -45.00  24.00   0.50    0.13    --  -47.65  37.00 -30.00  138
  5  ω    -44.00  24.00   0.50    0.13    --  -47.65  37.00-150.00  136
  6  ω    -53.00 -28.00   0.50    0.54    --  -91.75  45.00 -60.00   50
  7  ω   -151.00-123.00   0.50    0.54    --  -91.75 -78.00 -24.00   56
  8  ω    -91.00 -63.00   0.50    0.54    --  -91.75  78.00 100.00   56
  9  ω    113.00 152.00   0.50    0.54    --  113.25  61.00-180.00   78
 10  ω    132.00 172.00   0.50    0.54    --  113.25  77.00-180.00   80
 11  ω    108.00 173.00   0.50    0.54    --  113.25  78.00 100.00  130
 12  ω    149.00 175.00   0.50    0.54    --  113.25  45.00 150.00   52
 13  ω    103.00 142.00   0.50    0.54    --  113.25  45.00 150.00   78
 14  ω     39.00  65.00   0.50    0.13    --   47.65 -78.00 -24.00   52
 15  ω    -19.00  24.00   0.50    0.13    --   47.65 -78.00 -24.00   86
 16  ω     61.00  95.00   0.50    0.54    --  113.25 -78.00 -24.00   68
 17  ω     43.00  69.00   0.50    0.54    --  113.25 -61.00   0.00   52
 18  ω     50.00  92.00   0.50    0.54    --  113.25 -77.00  60.00   84
 19  ω     43.00  95.00   0.50    0.54    --  113.25 -77.00 150.00  104
 20  ω     42.00  67.00   0.50    0.54    --  113.25 -61.00 150.00   50
 21  ω     42.00  69.00   0.50    0.54    --  113.25 -61.00  90.00   54
 22  ω     42.00  67.00   0.50    0.54    --  113.25 -61.00  30.00   50
 23  ω     44.00  69.00   0.50    0.54    --  113.25 -61.00 -30.00   50
 24  ω     42.00  67.00   0.50    0.54    --  113.25 -61.00 -60.00   50
 25  ω     42.00  67.00   0.50    0.54    --  113.25 -61.00-180.00   50
 26  ω     46.00  72.00   0.50    0.54    --  113.25-125.00 -30.00   52
 27  ω     77.00 102.00   0.50    0.54    --  113.25-125.00 -30.00   50
 28  ω     48.00  94.00   0.50    0.54    --  113.25 -94.00 150.00   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      -0.1742677000
_diffrn_orient_matrix_UB_12      -0.0762212000
_diffrn_orient_matrix_UB_13      -0.0507676000
_diffrn_orient_matrix_UB_21      0.1419665000
_diffrn_orient_matrix_UB_22      -0.0588042000
_diffrn_orient_matrix_UB_23      0.2025569000
_diffrn_orient_matrix_UB_31      -0.0813303000
_diffrn_orient_matrix_UB_32      0.0606519000
_diffrn_orient_matrix_UB_33      0.1322984000
_diffrn_oxdiff_digest_hkl        
;
438a809e7ab858d0d657a6764a8d5620d5c1db
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name JS9325D.par
_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                1145
_reflns_number_total             1286
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.121a 64-bit (release 04-09-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.083
_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)+(0.0540P)²+0.1574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0989
_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
N1 N 0.18415(16) 0.42248(8) 0.69827(17) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.00419(16) 0.38303(8) 0.66076(17) 0.0189(3) Uani 1 1 d . . . . .
N3 N 0.11696(16) 0.22816(8) 0.59691(17) 0.0193(3) Uani 1 1 d . . . . .
N4 N 0.29668(16) 0.26715(8) 0.63221(17) 0.0188(3) Uani 1 1 d . . . . .
N5 N 0.52023(16) 0.39815(8) 0.71796(17) 0.0178(3) Uani 1 1 d . . . . .
N6 N 0.46082(16) 0.56650(8) 0.78080(17) 0.0187(3) Uani 1 1 d . . . . .
H6A H 0.512(2) 0.6283(12) 0.807(2) 0.017(4) Uiso 1 1 d . . . . .
H6B H 0.335(3) 0.5537(13) 0.758(3) 0.021(4) Uiso 1 1 d . . . . .
N7 N 0.77102(17) 0.51483(9) 0.80313(19) 0.0216(3) Uani 1 1 d . . . . .
H7A H 0.821(3) 0.5751(14) 0.837(3) 0.025(4) Uiso 1 1 d . . . . .
H7B H 0.840(3) 0.4691(15) 0.770(3) 0.032(5) Uiso 1 1 d . . . . .
N8 N -0.21146(17) 0.24654(9) 0.57864(18) 0.0208(3) Uani 1 1 d . . . . .
H8A H -0.302(3) 0.2871(14) 0.582(3) 0.034(5) Uiso 1 1 d . . . . .
H8B H -0.258(3) 0.1949(15) 0.489(3) 0.038(5) Uiso 1 1 d . . . . .
C1 C 0.32983(18) 0.36496(9) 0.68082(19) 0.0170(3) Uani 1 1 d . . . . .
C2 C -0.02831(19) 0.28713(9) 0.60845(19) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.57710(18) 0.49293(9) 0.76521(18) 0.0171(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3184(14) . ?
N1 C1 1.3594(16) . ?
N2 C2 1.3409(17) . ?
N3 N4 1.3182(14) . ?
N3 C2 1.3509(16) . ?
N4 C1 1.3617(16) . ?
N5 C1 1.3567(15) . ?
N5 C3 1.3427(17) . ?
N6 H6A 0.899(17) . ?
N6 H6B 0.865(17) . ?
N6 C3 1.3397(16) . ?
N7 H7A 0.880(19) . ?
N7 H7B 0.89(2) . ?
N7 C3 1.3369(16) . ?
N8 H8A 0.86(2) . ?
N8 H8B 0.90(2) . ?
N8 C2 1.3598(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 119.02(10) . . ?
N1 N2 C2 118.81(10) . . ?
N4 N3 C2 118.64(10) . . ?
N3 N4 C1 118.91(10) . . ?
C3 N5 C1 122.33(10) . . ?
H6A N6 H6B 121.5(15) . . ?
C3 N6 H6A 119.6(10) . . ?
C3 N6 H6B 118.7(11) . . ?
H7A N7 H7B 120.2(16) . . ?
C3 N7 H7A 121.8(11) . . ?
C3 N7 H7B 117.1(12) . . ?
H8A N8 H8B 117.7(17) . . ?
C2 N8 H8A 115.9(13) . . ?
C2 N8 H8B 117.1(12) . . ?
N1 C1 N4 121.60(11) . . ?
N5 C1 N1 123.60(11) . . ?
N5 C1 N4 114.75(10) . . ?
N2 C2 N3 122.97(11) . . ?
N2 C2 N8 118.13(11) . . ?
N3 C2 N8 118.78(11) . . ?
N6 C3 N5 126.70(11) . . ?
N7 C3 N5 115.95(11) . . ?
N7 C3 N6 117.35(11) . . ?

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 H6B N1 0.865(17) 2.028(17) 2.6633(16) 129.5(15) . yes
N7 H7A N3 0.880(19) 2.13(2) 2.9965(16) 169.1(15) 2_656 yes
N7 H7B N2 0.89(2) 2.04(2) 2.9230(15) 169.9(18) 1_655 yes
N8 H8B N5 0.90(2) 2.24(2) 3.0868(15) 158.5(17) 4_465 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 N3 1.52(18) . . . . ?
N1 N2 C2 N8 177.41(10) . . . . ?
N2 N1 C1 N4 -2.07(18) . . . . ?
N2 N1 C1 N5 -179.36(10) . . . . ?
N3 N4 C1 N1 1.46(18) . . . . ?
N3 N4 C1 N5 178.97(10) . . . . ?
N4 N3 C2 N2 -2.13(18) . . . . ?
N4 N3 C2 N8 -178.00(10) . . . . ?
C1 N1 N2 C2 0.59(17) . . . . ?
C1 N5 C3 N6 -0.58(19) . . . . ?
C1 N5 C3 N7 178.42(11) . . . . ?
C2 N3 N4 C1 0.60(17) . . . . ?
C3 N5 C1 N1 -3.42(19) . . . . ?
C3 N5 C1 N4 179.13(10) . . . . ?

_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 JS1515
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_js825c
_database_code_depnum_ccdc_archive 'CCDC 2491021'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2025-09-24 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
_audit_creation_date             2025-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C3 H7 N8), C2 N8 O4'
_chemical_formula_sum            'C8 H14 N24 O4'
_chemical_formula_weight         510.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C3N12O4
_chemical_oxdiff_usercomment     JS1516
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        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   21.5286(11)
_cell_length_b                   6.4729(5)
_cell_length_c                   13.4466(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.573(5)
_cell_angle_gamma                90
_cell_volume                     1871.92(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3109
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      76.5070
_cell_measurement_theta_min      4.0760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.117a (Rigaku Oxford Diffraction, 2025)
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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1101
0 1 0 0.1101
1 0 0 0.0165
-1 0 0 0.0095
0 0 -1 0.0102
0 0 1 0.0102

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.02
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
-0.0033 -0.9992 -0.0016 -0.0136 -0.2367 -0.0166
0.0033 0.9992 0.0016 0.0136 0.2367 0.0166
0.9991 0.0001 -0.0003 -0.0607 0.0009 0.0380
-0.9991 -0.0001 0.0003 0.0607 -0.0009 -0.0380
0.0030 -0.0064 -0.9976 0.0644 -0.0120 0.0939
-0.0030 0.0064 0.9976 -0.0644 0.0120 -0.0939

_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  0.0642
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6517
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.943
_diffrn_reflns_theta_min         6.591
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00 -21.00   0.50    1.00    --  -47.52 125.00 -54.00  122
  2  ω    -91.00 -66.00   0.50    1.00    --  -47.52-145.00  60.00   50
  3  ω     53.00  78.00   0.50    1.00    --   47.52-145.00  60.00   50
  4  ω     40.00  82.00   0.50    1.00    --   47.52-125.00-132.00   84
  5  ω    -85.00 -60.00   0.50    5.00    --  -91.75 145.00 112.00   50
  6  ω   -129.00 -75.00   0.50    5.00    --  -91.75-125.00-132.00  108
  7  ω     59.00 123.00   0.50    5.00    --  113.25-145.00  60.00  128
  8  ω     71.00  97.00   0.50    5.00    --  113.25-125.00-132.00   52
  9  ω    109.00 138.00   0.50    5.00    --  113.25 125.00 -54.00   58
 10  ω    -31.00  21.00   0.50    1.00    --  -47.52  19.00-150.00  104
 11  ω   -105.00 -80.00   0.50    1.00    --  -47.52 -37.00-150.00   50
 12  ω    -17.00  28.00   0.50    1.00    --   47.52 -19.00-150.00   90
 13  ω    -24.00   5.00   0.50    1.00    --   47.52 -19.00 120.00   58
 14  ω    -52.00 -21.00   0.50    5.00    --  -91.75  45.00-180.00   62
 15  ω    -51.00 -21.00   0.50    5.00    --  -91.75  45.00 120.00   60
 16  ω   -160.00-134.00   0.50    5.00    --  -91.75 -61.00 -30.00   52
 17  ω     44.00  88.00   0.50    5.00    --  113.25 -77.00  60.00   88
 18  ω    100.00 167.00   0.50    5.00    --  113.25 125.00 150.00  134
 19  ω     42.00  67.00   0.50    5.00    --  113.25 -61.00-120.00   50
 20  ω     74.00 100.00   0.50    5.00    --  113.25 -94.00-120.00   52
 21  ω     43.00  68.00   0.50    5.00    --  113.25 -94.00-120.00   50
 22  ω     42.00  90.00   0.50    5.00    --  113.25 -94.00 120.00   96
 23  ω     46.00  79.00   0.50    5.00    --  113.25 -94.00  60.00   66
 24  ω     78.00 103.00   0.50    5.00    --  113.25 -94.00 -90.00   50
 25  ω    130.00 178.00   0.50    5.00    --  113.25  77.00  90.00   96
 26  ω     42.00 102.00   0.50    5.00    --  113.25 -94.00-150.00  120
 27  ω     43.00  68.00   0.50    5.00    --  113.25 -61.00-180.00   50
 28  ω     77.00 102.00   0.50    5.00    --  113.25 -94.00-180.00   50
 29  ω    115.00 146.00   0.50    5.00    --  113.25  77.00-150.00   62
 30  ω    117.00 178.00   0.50    5.00    --  113.25  61.00   0.00  122
;
_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      -0.0607270000
_diffrn_orient_matrix_UB_12      0.0139626000
_diffrn_orient_matrix_UB_13      -0.0648084000
_diffrn_orient_matrix_UB_21      0.0009123000
_diffrn_orient_matrix_UB_22      0.2368549000
_diffrn_orient_matrix_UB_23      0.0104787000
_diffrn_orient_matrix_UB_31      0.0380106000
_diffrn_orient_matrix_UB_32      0.0166819000
_diffrn_orient_matrix_UB_33      -0.0940889000
_diffrn_oxdiff_digest_hkl        
;
43358cb1eabfc016e39736f75db2a8b6815967
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name JS825c.par
_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                1638
_reflns_number_total             1939
_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 1.171.44.117a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.117a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.117a (Rigaku OD, 2025)'
_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         -0.405
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.051
_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)+(0.1039P)²+0.3634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1513
_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
N1 N 0.63621(7) 0.6450(3) 0.68455(11) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.58382(7) 0.6985(3) 0.63950(11) 0.0246(4) Uani 1 1 d . . . . .
N3 N 0.67491(7) 0.5383(3) 0.52744(11) 0.0268(4) Uani 1 1 d . . . . .
N4 N 0.52088(7) 0.7414(3) 0.49957(11) 0.0242(4) Uani 1 1 d . . . . .
H4 H 0.4944(11) 0.783(4) 0.5450(18) 0.028(6) Uiso 1 1 d . . . . .
N5 N 0.53743(7) 0.6832(3) 0.33202(11) 0.0280(4) Uani 1 1 d . . . . .
H5A H 0.5273(13) 0.697(5) 0.271(2) 0.039(7) Uiso 1 1 d . . . . .
H5B H 0.5773(13) 0.653(5) 0.3469(19) 0.040(7) Uiso 1 1 d . . . . .
N6 N 0.44368(7) 0.8092(3) 0.38136(12) 0.0271(4) Uani 1 1 d . . . . .
H6A H 0.4278(12) 0.797(4) 0.320(2) 0.034(6) Uiso 1 1 d . . . . .
H6B H 0.4214(12) 0.845(4) 0.431(2) 0.034(6) Uiso 1 1 d . . . . .
N11 N 0.62074(7) 0.5950(3) 0.48347(11) 0.0256(4) Uani 1 1 d . . . . .
N14 N 0.73655(7) 0.5289(3) 0.67317(13) 0.0298(4) Uani 1 1 d . . . . .
H14A H 0.7384(13) 0.527(5) 0.739(2) 0.045(8) Uiso 1 1 d . . . . .
H14B H 0.7623(18) 0.475(6) 0.641(3) 0.065(10) Uiso 1 1 d . . . . .
C1 C 0.68226(8) 0.5706(3) 0.62636(13) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.57830(8) 0.6768(3) 0.53990(12) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.50125(8) 0.7444(3) 0.40195(13) 0.0247(4) Uani 1 1 d . . . . .
O6 O 0.35152(5) 0.7351(2) 0.69658(9) 0.0289(4) Uani 1 1 d . . . . .
O7 O 0.44553(5) 0.8169(2) 0.65875(9) 0.0276(4) Uani 1 1 d . . . . .
N7 N 0.38707(6) 0.8230(3) 0.63941(10) 0.0241(4) Uani 1 1 d . . . . .
N8 N 0.37012(6) 0.9173(3) 0.55640(11) 0.0250(4) Uani 1 1 d . . . . .
N9 N 0.29556(7) 0.9589(3) 0.43390(11) 0.0265(4) Uani 1 1 d . . . . .
N10 N 0.26290(7) 0.9588(3) 0.59992(11) 0.0257(4) Uani 1 1 d . . . . .
C4 C 0.30707(8) 0.9345(3) 0.53268(13) 0.0236(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
N1 N2 1.303(2) . ?
N1 C1 1.377(2) . ?
N2 C2 1.347(2) . ?
N3 N11 1.335(2) . ?
N3 C1 1.349(2) . ?
N4 H4 0.90(3) . ?
N4 C2 1.392(2) . ?
N4 C3 1.361(2) . ?
N5 H5A 0.85(3) . ?
N5 H5B 0.90(3) . ?
N5 C3 1.309(2) . ?
N6 H6A 0.88(3) . ?
N6 H6B 0.87(3) . ?
N6 C3 1.326(2) . ?
N11 C2 1.324(2) . ?
N14 H14A 0.88(3) . ?
N14 H14B 0.80(4) . ?
N14 C1 1.330(2) . ?
O6 N7 1.246(2) . ?
O7 N7 1.2743(17) . ?
N7 N8 1.310(2) . ?
N8 C4 1.385(2) . ?
N9 N10 1.3187(19) 2_556 ?
N9 C4 1.349(2) . ?
N10 C4 1.350(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 117.32(15) . . ?
N1 N2 C2 118.08(14) . . ?
N11 N3 C1 117.10(15) . . ?
C2 N4 H4 113.9(15) . . ?
C3 N4 H4 118.3(15) . . ?
C3 N4 C2 127.73(15) . . ?
H5A N5 H5B 116(3) . . ?
C3 N5 H5A 122.1(19) . . ?
C3 N5 H5B 120.1(17) . . ?
H6A N6 H6B 122(2) . . ?
C3 N6 H6A 119.1(17) . . ?
C3 N6 H6B 118.0(17) . . ?
C2 N11 N3 117.88(14) . . ?
H14A N14 H14B 122(3) . . ?
C1 N14 H14A 118.4(19) . . ?
C1 N14 H14B 117(3) . . ?
N3 C1 N1 123.98(16) . . ?
N14 C1 N1 116.22(16) . . ?
N14 C1 N3 119.80(16) . . ?
N2 C2 N4 113.16(15) . . ?
N11 C2 N2 125.40(16) . . ?
N11 C2 N4 121.38(15) . . ?
N5 C3 N4 121.30(17) . . ?
N5 C3 N6 121.77(16) . . ?
N6 C3 N4 116.93(16) . . ?
O6 N7 O7 119.23(14) . . ?
O6 N7 N8 125.67(14) . . ?
O7 N7 N8 115.04(14) . . ?
N7 N8 C4 117.81(14) . . ?
N10 N9 C4 118.01(15) 2_556 . ?
N9 N10 C4 117.32(15) 2_556 . ?
N9 C4 N8 111.77(15) . . ?
N9 C4 N10 122.80(17) . . ?
N10 C4 N8 124.58(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O7 0.90(3) 1.91(3) 2.7863(19) 167(2) . yes
N5 H5A N2 0.85(3) 2.29(3) 2.919(2) 131(2) 8_564 yes
N5 H5A O7 0.85(3) 2.26(3) 2.988(2) 143(2) 8_564 yes
N5 H5B N11 0.90(3) 2.06(3) 2.713(2) 129(2) . yes
N6 H6B N8 0.87(3) 2.11(3) 2.979(2) 176(3) . yes
N14 H14A N10 0.88(3) 2.22(3) 3.084(2) 169(3) 4_546 yes
N14 H14B O6 0.80(4) 2.44(4) 3.013(2) 129(3) 6_665 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C2 N4 -179.08(16) . . . . ?
N1 N2 C2 N11 3.7(3) . . . . ?
N2 N1 C1 N3 -4.3(3) . . . . ?
N2 N1 C1 N14 176.05(17) . . . . ?
N3 N11 C2 N2 -3.6(3) . . . . ?
N3 N11 C2 N4 179.44(16) . . . . ?
N11 N3 C1 N1 4.4(3) . . . . ?
N11 N3 C1 N14 -175.94(18) . . . . ?
C1 N1 N2 C2 0.2(3) . . . . ?
C1 N3 N11 C2 -0.5(3) . . . . ?
C2 N4 C3 N5 -0.4(3) . . . . ?
C2 N4 C3 N6 178.67(18) . . . . ?
C3 N4 C2 N2 178.31(18) . . . . ?
C3 N4 C2 N11 -4.4(3) . . . . ?
O6 N7 N8 C4 4.8(3) . . . . ?
O7 N7 N8 C4 -178.12(16) . . . . ?
N7 N8 C4 N9 -156.29(17) . . . . ?
N7 N8 C4 N10 34.0(3) . . . . ?
N9 N10 C4 N8 -175.56(18) 2_556 . . . ?
N9 N10 C4 N9 15.9(3) 2_556 . . . ?
N10 N9 C4 N8 174.09(17) 2_556 . . . ?
N10 N9 C4 N10 -16.0(3) 2_556 . . . ?

_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 JS1516
_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 3.234
_oxdiff_exptl_absorpt_empirical_full_min 0.348
####################################################################### 
# 
# 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_js825e
_database_code_depnum_ccdc_archive 'CCDC 2491020'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2025-09-24 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
_audit_creation_date             2025-08-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
staples@chemistry.msu.edu
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H10 N10, C2 N10'
_chemical_formula_sum            'C6 H10 N20'
_chemical_formula_weight         362.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H10N2O
_chemical_oxdiff_usercomment     JS11511
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'

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

_cell_length_a                   7.4904(2)
_cell_length_b                   7.3959(2)
_cell_length_c                   12.6706(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.508(3)
_cell_angle_gamma                90
_cell_volume                     701.69(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      78.5490
_cell_measurement_theta_min      6.7870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.117a (Rigaku Oxford Diffraction, 2025)
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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0372
0 -1 0 0.0312
1 0 1 0.1732
-1 0 -1 0.1404
0 1 1 0.0415
0 -1 -1 0.0267
-2 0 7 0.1022
3 0 -7 0.1226
0 0 1 0.0248
0 0 -1 0.0248

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.05
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
0.0077 1.0022 0.0058 -0.0129 0.0515 0.2014
-0.0077 -1.0022 -0.0063 0.0129 -0.0515 -0.2014
0.9957 -0.0078 1.0037 0.0351 -0.2313 0.0613
-0.9957 0.0078 -1.0037 -0.0351 0.2313 -0.0613
0.0012 0.9999 1.0060 -0.1063 -0.0253 0.2151
-0.0019 -1.0000 -1.0024 0.1059 0.0252 -0.2151
-2.4173 0.1846 7.2240 -0.9823 -0.1804 0.0241
2.5354 0.3327 -7.0969 0.9788 0.1798 0.0872
0.0005 -0.0008 0.9992 -0.0925 -0.0778 0.0143
-0.0005 0.0008 -0.9992 0.0925 0.0778 -0.0143

_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4933
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.202
_diffrn_reflns_theta_min         6.789
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -138.00-102.00   0.50    0.48    --  -91.75-125.00-150.00   72
  2  ω   -108.00 -37.00   0.50    0.12    --  -47.65 -43.00  62.00  142
  3  ω   -164.00-139.00   0.50    0.48    --  -91.75 -43.00  62.00   50
  4  ω   -125.00 -78.00   0.50    0.48    --  -91.75 -43.00  62.00   94
  5  ω    -22.00  26.00   0.50    0.12    --  -47.65  19.00   0.00   96
  6  ω    -51.00 -26.00   0.50    0.48    --  -91.75  45.00 150.00   50
  7  ω    -47.00 -21.00   0.50    0.48    --  -91.75  45.00  60.00   52
  8  ω    -45.00 -19.00   0.50    0.48    --  -91.75  43.00-145.00   52
  9  ω    -28.00  25.00   0.50    0.12    --  -47.65  43.00-145.00  106
 10  ω     69.00  95.00   0.50    0.48    --  113.25 -94.00-150.00   52
 11  ω     42.00 102.00   0.50    0.48    --  113.25 -94.00  60.00  120
 12  ω    151.00 176.00   0.50    0.48    --  113.25  15.00 -60.00   50
 13  ω     54.00 107.00   0.50    0.12    --   47.65  43.00-145.00  106
 14  ω    126.00 172.00   0.50    0.48    --  113.25  77.00 -60.00   92
 15  ω    101.00 176.00   0.50    0.48    --  113.25  43.00-145.00  150
 16  ω    151.00 177.00   0.50    0.48    --  113.25  61.00  90.00   52
 17  ω    113.00 142.00   0.50    0.48    --  113.25  61.00  90.00   58
 18  ω    113.00 171.00   0.50    0.48    --  113.25  61.00 150.00  116
 19  ω     53.00  93.00   0.50    0.48    --  113.25 -77.00   0.00   80
 20  ω     42.00  77.00   0.50    0.48    --  113.25 -77.00  60.00   70
 21  ω     47.00  88.00   0.50    0.48    --  113.25 -77.00 -30.00   82
 22  ω     42.00  67.00   0.50    0.48    --  113.25 -61.00  90.00   50
 23  ω     43.00  68.00   0.50    0.48    --  113.25 -61.00 -30.00   50
 24  ω     42.00  67.00   0.50    0.48    --  113.25 -61.00 -60.00   50
 25  ω     54.00  94.00   0.50    0.48    --  113.25 -77.00 -90.00   80
 26  ω     42.00  67.00   0.50    0.48    --  113.25 -61.00-150.00   50
 27  ω    -12.00  13.00   0.50    0.12    --   47.65 -43.00  62.00   50
 28  ω     42.00  67.00   0.50    0.48    --  113.25 -61.00 120.00   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      0.1285144000
_diffrn_orient_matrix_UB_12      -0.0132852000
_diffrn_orient_matrix_UB_13      -0.0926338000
_diffrn_orient_matrix_UB_21      -0.1535285000
_diffrn_orient_matrix_UB_22      0.0530177000
_diffrn_orient_matrix_UB_23      -0.0776963000
_diffrn_orient_matrix_UB_31      0.0485300000
_diffrn_orient_matrix_UB_32      0.2004882000
_diffrn_orient_matrix_UB_33      0.0144527000
_diffrn_oxdiff_digest_hkl        
;
43fc6fcd1fff371e1ff8cdbdca707d59adb798
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name JS825E.par
_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                1319
_reflns_number_total             1428
_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 1.171.44.117a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.117a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.117a (Rigaku OD, 2025)'
_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         0.467
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.090
_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)+(0.0558P)²+0.2752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1068
_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
N1 N 0.39033(15) 0.31682(15) 0.42675(9) 0.0157(3) Uani 1 1 d . . . . .
N9 N 0.01925(15) 0.71109(16) 0.65349(9) 0.0173(3) Uani 1 1 d . . . . .
N5 N 0.36137(16) 0.56485(16) 0.31999(10) 0.0181(3) Uani 1 1 d . . . . .
N6 N 0.16407(15) 0.69881(15) 0.50252(9) 0.0171(3) Uani 1 1 d . . . . .
N7 N 0.19021(15) 0.54667(15) 0.55790(9) 0.0176(3) Uani 1 1 d . . . . .
N10 N -0.01090(15) 0.97018(15) 0.54600(9) 0.0167(3) Uani 1 1 d . . . . .
N3 N 0.59714(15) -0.11318(15) 0.43833(9) 0.0176(3) Uani 1 1 d . . . . .
N4 N 0.49800(16) 0.31171(16) 0.25433(10) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.54186(15) 0.04269(15) 0.39902(9) 0.0174(3) Uani 1 1 d . . . . .
N8 N 0.10326(15) 0.55253(15) 0.64766(9) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.44716(17) 0.15045(18) 0.46196(10) 0.0151(3) Uani 1 1 d . . . . .
C8 C 0.05735(17) 0.79652(18) 0.56368(11) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.41887(17) 0.39684(18) 0.33166(10) 0.0158(3) Uani 1 1 d . . . . .
H4A H 0.536(2) 0.201(3) 0.2643(15) 0.026(5) Uiso 1 1 d . . . . .
H5A H 0.404(3) 0.626(3) 0.2692(16) 0.028(5) Uiso 1 1 d . . . . .
H1 H 0.334(3) 0.374(3) 0.4734(18) 0.039(6) Uiso 1 1 d . . . . .
H4B H 0.503(3) 0.369(3) 0.1926(17) 0.028(5) Uiso 1 1 d . . . . .
H5B H 0.300(3) 0.613(3) 0.3723(17) 0.033(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3727(18) . ?
N1 C2 1.3643(17) . ?
N1 H1 0.85(2) . ?
N9 N8 1.3338(16) . ?
N9 C8 1.3389(18) . ?
N5 C2 1.3221(18) . ?
N5 H5A 0.86(2) . ?
N5 H5B 0.89(2) . ?
N6 N7 1.3378(17) . ?
N6 C8 1.3396(17) . ?
N7 N8 1.3261(16) . ?
N10 N10 1.261(2) 3_576 ?
N10 C8 1.3982(18) . ?
N3 N2 1.3182(16) . ?
N3 C1 1.3432(17) 3_656 ?
N4 C2 1.3184(17) . ?
N4 H4A 0.87(2) . ?
N4 H4B 0.89(2) . ?
N2 C1 1.3432(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 112.2(15) . . ?
C2 N1 C1 128.42(12) . . ?
C2 N1 H1 119.4(15) . . ?
N8 N9 C8 104.86(11) . . ?
C2 N5 H5A 117.3(13) . . ?
C2 N5 H5B 117.9(14) . . ?
H5A N5 H5B 123.6(19) . . ?
N7 N6 C8 103.39(11) . . ?
N8 N7 N6 110.73(10) . . ?
N10 N10 C8 114.44(14) 3_576 . ?
N2 N3 C1 116.87(12) . 3_656 ?
C2 N4 H4A 119.3(13) . . ?
C2 N4 H4B 117.2(13) . . ?
H4A N4 H4B 123.3(18) . . ?
N3 N2 C1 117.39(12) . . ?
N7 N8 N9 108.62(11) . . ?
N3 C1 N1 114.05(12) 3_656 . ?
N2 C1 N1 120.20(12) . . ?
N2 C1 N3 125.74(13) . 3_656 ?
N9 C8 N6 112.39(12) . . ?
N9 C8 N10 118.98(12) . . ?
N6 C8 N10 128.61(12) . . ?
N5 C2 N1 116.63(12) . . ?
N4 C2 N1 122.22(12) . . ?
N4 C2 N5 121.15(12) . . ?

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
N4 H4A N2 0.87(2) 2.07(2) 2.7195(17) 130.5(16) . yes
N5 H5A N9 0.86(2) 2.10(2) 2.9541(16) 175.5(19) 4_675 yes
N1 H1 N7 0.85(2) 2.00(2) 2.8336(16) 168(2) . yes
N4 H4B N10 0.89(2) 2.21(2) 3.0927(16) 173.3(18) 4_675 yes
N5 H5B N6 0.89(2) 2.06(2) 2.9486(16) 174(2) . 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
N6 N7 N8 N9 -0.72(15) . . . . ?
N7 N6 C8 N9 0.50(15) . . . . ?
N7 N6 C8 N10 178.78(13) . . . . ?
N10 N10 C8 N9 -170.72(14) 3_576 . . . ?
N10 N10 C8 N6 11.1(2) 3_576 . . . ?
N3 N2 C1 N1 178.06(11) . . . . ?
N3 N2 C1 N3 -0.3(2) . . . 3_656 ?
N8 N9 C8 N6 -0.92(16) . . . . ?
N8 N9 C8 N10 -179.39(11) . . . . ?
C1 N1 C2 N5 -174.88(12) . . . . ?
C1 N1 C2 N4 5.8(2) . . . . ?
C1 N3 N2 C1 0.3(2) 3_656 . . . ?
C8 N9 N8 N7 0.97(14) . . . . ?
C8 N6 N7 N8 0.14(14) . . . . ?
C2 N1 C1 N3 177.50(12) . . . 3_656 ?
C2 N1 C1 N2 -1.1(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JS1511
_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 1.988
_oxdiff_exptl_absorpt_empirical_full_min 0.396
