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

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

data_js721d
_audit_block_doi                 10.5517/ccdc.csd.cc28j7tw
_database_code_depnum_ccdc_archive 'CCDC 2100988'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2QM00092J 2022
loop_
_audit_author_name
_audit_author_address
'Dr. Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2021-08-02 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 N6 O8, 2(C3 H7 N8)'
_chemical_formula_sum            'C12 H16 N22 O8'
_chemical_formula_weight         596.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H16N22O8
_chemical_oxdiff_usercomment     JS57F
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.74834(15)
_cell_length_b                   8.47996(19)
_cell_length_c                   20.5330(3)
_cell_angle_alpha                92.5744(15)
_cell_angle_beta                 94.2528(16)
_cell_angle_gamma                109.608(2)
_cell_volume                     1100.78(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9141
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      79.4380
_cell_measurement_theta_min      4.3180
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    1.331
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             612
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0242
0 0 -1 0.0174
0 1 0 0.0204
0 -1 0 0.0085
1 -1 -1 0.0667
-1 1 1 0.0871
0 -1 1 0.0095
0 5 -6 0.0214
0 3 -11 0.0148

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.029
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
-0.0006 0.0008 0.9998 -0.0571 -0.0033 0.0492
0.0006 -0.0008 -0.9998 0.0571 0.0033 -0.0492
0.0013 0.9997 0.0002 -0.0895 0.1563 -0.0706
-0.0013 -0.9997 -0.0002 0.0895 -0.1563 0.0706
1.0001 -1.0010 -0.9993 0.2131 0.0449 0.1471
-1.0001 1.0010 0.9993 -0.2131 -0.0449 -0.1471
-0.0019 -0.9989 0.9996 0.0324 -0.1596 0.1199
-0.4423 4.9278 -6.0000 -0.1291 0.7017 -0.7007
-0.0239 3.2579 -10.9456 0.3300 0.5404 -0.7740

_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14565
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.222
_diffrn_reflns_theta_min         4.330
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_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 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -30.00   0.50    0.29    --  -47.36 -66.00 -64.00  148
  2  ω    -25.00  25.00   0.50    0.29    --  -47.36  66.00  70.00  100
  3  ω    -61.00 -30.00   0.50    0.29    --  -47.36  66.00  70.00   62
  4  ω     65.00 115.00   0.50    0.29    --   47.36  66.00  70.00  100
  5  ω     30.00  59.00   0.50    0.29    --   47.36  66.00  70.00   58
  6  ω    -54.00 -28.00   0.50    1.17    --  -91.75  66.00  70.00   52
  7  ω     42.00  67.00   0.50    1.17    --  113.25 -66.00 -64.00   50
  8  ω     95.00 121.00   0.50    1.17    --  113.25  66.00  70.00   52
  9  ω    -77.00 -32.00   0.50    0.29    --  -47.36 125.00-150.00   90
 10  ω    -25.00  18.00   0.50    0.29    --  -47.36  19.00  60.00   86
 11  ω    -27.00  22.00   0.50    0.29    --   47.36 -19.00  30.00   98
 12  ω     35.00  65.00   0.50    0.29    --   47.36 -66.00 -64.00   60
 13  ω    -20.00  10.00   0.50    0.29    --   47.36 -66.00 -64.00   60
 14  ω   -155.00-128.00   0.50    1.17    --  -91.75 -61.00  30.00   54
 15  ω    -77.00 -29.00   0.50    1.17    --  -91.75 125.00  60.00   96
 16  ω   -162.00-122.00   0.50    1.17    --  -91.75 -45.00-180.00   80
 17  ω   -160.00-133.00   0.50    1.17    --  -91.75 -61.00 -90.00   54
 18  ω    -49.00 -22.00   0.50    1.17    --  -91.75  45.00 -90.00   54
 19  ω   -159.00-133.00   0.50    1.17    --  -91.75 -77.00  60.00   52
 20  ω   -117.00 -74.00   0.50    1.17    --  -91.75 -66.00 -64.00   86
 21  ω    -52.00 -26.00   0.50    1.17    --  -91.75  45.00  60.00   52
 22  ω     43.00  93.00   0.50    1.17    --  113.25-125.00  30.00  100
 23  ω     43.00 100.00   0.50    1.17    --  113.25-125.00-180.00  114
 24  ω     76.00 108.00   0.50    1.17    --  113.25-125.00-150.00   64
 25  ω    123.00 175.00   0.50    1.17    --  113.25  45.00   0.00  104
 26  ω     42.00  71.00   0.50    1.17    --  113.25 -94.00-150.00   58
 27  ω     44.00 102.00   0.50    1.17    --  113.25 -94.00  30.00  116
 28  ω     43.00  94.00   0.50    1.17    --  113.25 -94.00 -60.00  102
 29  ω    122.00 156.00   0.50    1.17    --  113.25  45.00 150.00   68
 30  ω    122.00 156.00   0.50    1.17    --  113.25  45.00 -60.00   68
 31  ω    127.00 153.00   0.50    1.17    --  113.25  77.00 150.00   52
 32  ω    122.00 166.00   0.50    1.17    --  113.25  45.00  90.00   88
 33  ω     72.00  98.00   0.50    1.17    --  113.25 -94.00-150.00   52
 34  ω    142.00 167.00   0.50    1.17    --  113.25  77.00   0.00   50
 35  ω     79.00 104.00   0.50    1.17    --  113.25 -94.00-120.00   50
 36  ω     42.00  67.00   0.50    1.17    --  113.25 -61.00  90.00   50
 37  ω     77.00 103.00   0.50    1.17    --  113.25 -94.00  90.00   52
 38  ω     45.00  70.00   0.50    1.17    --  113.25 -61.00 120.00   50
 39  ω     79.00 104.00   0.50    1.17    --  113.25 -94.00 120.00   50
 40  ω     58.00 103.00   0.50    1.17    --  113.25 -98.00   5.04   90
 41  ω     42.00  70.00   0.50    1.17    --  113.25 -61.00-180.00   56
 42  ω     47.00  75.00   0.50    1.17    --  113.25 -94.00-120.00   56
 43  ω     76.00 104.00   0.50    1.17    --  113.25 -94.00-180.00   56
 44  ω     44.00  70.00   0.50    1.17    --  113.25 -94.00 120.00   52
 45  ω     46.00  72.00   0.50    1.17    --  113.25 -77.00-120.00   52
 46  ω    123.00 177.00   0.50    1.17    --  113.25  45.00  60.00  108
 47  ω     44.00  99.00   0.50    1.17    --  113.25 -94.00  60.00  110
 48  ω    136.00 167.00   0.50    1.17    --  113.25  61.00 -90.00   62
 49  ω     42.00  68.00   0.50    1.17    --  113.25 -94.00-180.00   52
 50  ω     42.00  67.00   0.50    1.17    --  113.25 -61.00 -60.00   50
 51  ω    134.00 175.00   0.50    1.17    --  113.25  61.00-180.00   82
 52  ω    141.00 178.00   0.50    1.17    --  113.25  61.00  30.00   74
 53  ω     50.00  93.00   0.50    1.17    --  113.25 -94.00 -90.00   86
 54  ω     77.00 103.00   0.50    1.17    --  113.25 -97.00 -38.67   52
 55  ω    137.00 178.00   0.50    1.17    --  113.25  45.00 -30.00   82
;
_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      0.0664822000
_diffrn_orient_matrix_UB_12      -0.0895959000
_diffrn_orient_matrix_UB_13      -0.0569633000
_diffrn_orient_matrix_UB_21      0.1977440000
_diffrn_orient_matrix_UB_22      0.1560558000
_diffrn_orient_matrix_UB_23      -0.0033537000
_diffrn_orient_matrix_UB_31      0.1254549000
_diffrn_orient_matrix_UB_32      -0.0708401000
_diffrn_orient_matrix_UB_33      0.0493537000
_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                4085
_reflns_number_total             4679
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         4679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.058
_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)+(0.0469P)²+0.4227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.34502(16) 0.57571(13) 0.81565(5) 0.0211(2) Uani 1 1 d . . . . .
O2 O 1.08031(16) 0.40886(13) 0.86245(5) 0.0191(2) Uani 1 1 d . . . . .
O3 O 0.19537(17) 0.01477(14) 0.61077(5) 0.0197(2) Uani 1 1 d . . . . .
O4 O 0.30220(17) -0.16893(15) 0.55817(5) 0.0241(2) Uani 1 1 d . . . . .
O5 O 0.19047(17) -0.14677(13) 0.72570(5) 0.0216(2) Uani 1 1 d . . . . .
O6 O 0.07252(17) 0.04420(15) 0.76333(6) 0.0231(2) Uani 1 1 d . . . . .
O7 O 0.65616(17) 0.47187(14) 0.89359(5) 0.0207(2) Uani 1 1 d . . . . .
O8 O 0.86141(17) 0.64027(13) 0.83087(5) 0.0211(2) Uani 1 1 d . . . . .
N1 N 1.05219(19) 0.44381(16) 0.75347(6) 0.0179(3) Uani 1 1 d . . . . .
N2 N 1.15471(19) 0.47554(15) 0.81065(6) 0.0164(2) Uani 1 1 d . . . . .
N3 N 0.51429(19) -0.01160(16) 0.63841(6) 0.0174(3) Uani 1 1 d . . . . .
N4 N 0.33209(19) -0.05338(16) 0.60328(6) 0.0174(2) Uani 1 1 d . . . . .
N5 N 0.21162(19) -0.00010(16) 0.74108(6) 0.0169(2) Uani 1 1 d . . . . .
N6 N 0.74155(19) 0.50200(15) 0.84236(6) 0.0169(2) Uani 1 1 d . . . . .
C1 C 0.8382(2) 0.34388(18) 0.75104(7) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.7642(2) 0.21873(18) 0.70000(7) 0.0167(3) Uani 1 1 d . . . . .
H2 H 0.860570 0.206897 0.670279 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5548(2) 0.10968(18) 0.69044(7) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.4179(2) 0.12728(18) 0.73666(7) 0.0160(3) Uani 1 1 d . . . . .
C5 C 0.4820(2) 0.25637(18) 0.78554(7) 0.0162(3) Uani 1 1 d . . . . .
H5 H 0.385065 0.270368 0.814625 0.019 Uiso 1 1 calc R U . . .
C6 C 0.6886(2) 0.36473(17) 0.79158(7) 0.0158(3) Uani 1 1 d . . . . .
N7 N 0.84479(19) 0.07905(16) 0.91781(6) 0.0174(3) Uani 1 1 d . . . . .
N8 N 1.0376(2) 0.05555(18) 0.91093(7) 0.0208(3) Uani 1 1 d . . . . .
H8A H 1.025(3) -0.058(3) 0.9119(10) 0.027(5) Uiso 1 1 d . . . . .
H8B H 1.076(4) 0.090(3) 0.8744(12) 0.031(6) Uiso 1 1 d . . . . .
N9 N 0.9197(2) 0.28877(17) 1.01432(6) 0.0198(3) Uani 1 1 d . . . . .
N10 N 0.7575(2) 0.33879(17) 1.03780(6) 0.0191(3) Uani 1 1 d . . . . .
H10 H 0.789(3) 0.418(3) 1.0704(11) 0.029(5) Uiso 1 1 d . . . . .
N11 N 0.60484(19) 0.15676(15) 0.95885(6) 0.0159(2) Uani 1 1 d . . . . .
N12 N 0.49448(19) 0.04517(16) 0.90546(6) 0.0170(3) Uani 1 1 d . . . . .
N13 N 0.6283(2) -0.09964(17) 0.82853(6) 0.0197(3) Uani 1 1 d . . . . .
H13A H 0.501(4) -0.178(3) 0.8163(10) 0.028(5) Uiso 1 1 d . . . . .
H13B H 0.739(4) -0.124(3) 0.8167(10) 0.025(5) Uiso 1 1 d . . . . .
N14 N 0.3821(2) 0.27506(18) 1.01288(7) 0.0215(3) Uani 1 1 d . . . . .
H14A H 0.281(4) 0.228(3) 0.9843(11) 0.025(5) Uiso 1 1 d . . . . .
H14B H 0.364(4) 0.347(3) 1.0424(11) 0.030(5) Uiso 1 1 d . . . . .
C7 C 0.6489(2) 0.00232(18) 0.88208(7) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.8142(2) 0.18024(19) 0.96630(7) 0.0167(3) Uani 1 1 d . . . . .
C9 C 0.5683(2) 0.26090(18) 1.00442(7) 0.0174(3) Uani 1 1 d . . . . .
N15 N 0.49706(19) 0.53100(16) 0.63201(6) 0.0174(3) Uani 1 1 d . . . . .
N16 N 0.5157(2) 0.64756(17) 0.68431(6) 0.0198(3) Uani 1 1 d . . . . .
H16A H 0.497(3) 0.736(3) 0.6693(10) 0.019(5) Uiso 1 1 d . . . . .
H16B H 0.422(4) 0.601(3) 0.7135(12) 0.034(6) Uiso 1 1 d . . . . .
N17 N 0.1220(2) 0.40412(16) 0.58170(6) 0.0197(3) Uani 1 1 d . . . . .
N18 N 0.0692(2) 0.28565(16) 0.52755(6) 0.0191(3) Uani 1 1 d . . . . .
H18 H -0.061(4) 0.251(3) 0.5055(12) 0.035(6) Uiso 1 1 d . . . . .
N19 N 0.40058(19) 0.34781(16) 0.54906(6) 0.0161(2) Uani 1 1 d . . . . .
N20 N 0.61993(19) 0.38602(16) 0.55816(6) 0.0175(2) Uani 1 1 d . . . . .
N21 N 0.2397(2) 0.14523(17) 0.45883(6) 0.0214(3) Uani 1 1 d . . . . .
H21A H 0.119(4) 0.093(3) 0.4315(11) 0.031(5) Uiso 1 1 d . . . . .
H21B H 0.351(4) 0.137(3) 0.4491(12) 0.034(6) Uiso 1 1 d . . . . .
N22 N 0.8648(2) 0.58491(17) 0.63556(7) 0.0189(3) Uani 1 1 d . . . . .
H22A H 0.966(4) 0.545(3) 0.6235(11) 0.029(5) Uiso 1 1 d . . . . .
H22B H 0.879(3) 0.644(3) 0.6716(12) 0.028(5) Uiso 1 1 d . . . . .
C10 C 0.6696(2) 0.49938(18) 0.60888(7) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.3250(2) 0.43484(18) 0.59168(7) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.2355(2) 0.25127(19) 0.50754(7) 0.0177(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.2736(16) . ?
O2 N2 1.2830(17) . ?
O3 N4 1.2569(16) . ?
O4 N4 1.2716(16) . ?
O5 N5 1.2271(17) . ?
O6 N5 1.2312(17) . ?
O7 N6 1.2324(17) . ?
O8 N6 1.2254(17) . ?
N1 N2 1.2867(18) . ?
N1 C1 1.4039(19) . ?
N3 N4 1.3080(17) . ?
N3 C3 1.3939(18) . ?
N5 C4 1.4601(19) . ?
N6 C6 1.4583(17) . ?
C1 C2 1.393(2) . ?
C1 C6 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(2) . ?
C3 C4 1.409(2) . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(2) . ?
N7 N8 1.3966(17) . ?
N7 C7 1.3947(18) . ?
N7 C8 1.3575(19) . ?
N8 H8A 0.94(2) . ?
N8 H8B 0.85(2) . ?
N9 N10 1.4081(17) . ?
N9 C8 1.304(2) . ?
N10 H10 0.89(2) . ?
N10 C9 1.3414(19) . ?
N11 N12 1.4016(16) . ?
N11 C8 1.3547(18) . ?
N11 C9 1.3500(19) . ?
N12 C7 1.3270(19) . ?
N13 H13A 0.90(2) . ?
N13 H13B 0.89(2) . ?
N13 C7 1.3369(19) . ?
N14 H14A 0.84(2) . ?
N14 H14B 0.88(2) . ?
N14 C9 1.325(2) . ?
N15 N16 1.3956(17) . ?
N15 C10 1.3904(18) . ?
N15 C11 1.3639(19) . ?
N16 H16A 0.87(2) . ?
N16 H16B 0.91(3) . ?
N17 N18 1.4048(17) . ?
N17 C11 1.3043(19) . ?
N18 H18 0.90(2) . ?
N18 C12 1.338(2) . ?
N19 N20 1.4010(16) . ?
N19 C11 1.3533(19) . ?
N19 C12 1.3499(19) . ?
N20 C10 1.3278(19) . ?
N21 H21A 0.92(2) . ?
N21 H21B 0.81(3) . ?
N21 C12 1.323(2) . ?
N22 H22A 0.90(2) . ?
N22 H22B 0.85(2) . ?
N22 C10 1.3332(19) . ?

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 115.76(12) . . ?
O1 N2 O2 117.90(11) . . ?
O1 N2 N1 117.68(12) . . ?
O2 N2 N1 124.38(12) . . ?
N4 N3 C3 117.86(12) . . ?
O3 N4 O4 120.75(12) . . ?
O3 N4 N3 124.59(12) . . ?
O4 N4 N3 114.64(12) . . ?
O5 N5 O6 123.67(13) . . ?
O5 N5 C4 117.91(12) . . ?
O6 N5 C4 118.29(12) . . ?
O7 N6 C6 117.25(12) . . ?
O8 N6 O7 124.21(12) . . ?
O8 N6 C6 118.49(12) . . ?
N1 C1 C6 126.84(13) . . ?
C2 C1 N1 116.08(13) . . ?
C2 C1 C6 116.91(13) . . ?
C1 C2 H2 118.4 . . ?
C1 C2 C3 123.11(13) . . ?
C3 C2 H2 118.4 . . ?
N3 C3 C2 114.40(13) . . ?
N3 C3 C4 128.49(13) . . ?
C2 C3 C4 116.91(13) . . ?
C3 C4 N5 122.18(13) . . ?
C5 C4 N5 115.84(13) . . ?
C5 C4 C3 121.53(13) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.22(13) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 N6 122.15(13) . . ?
C5 C6 N6 115.96(12) . . ?
C5 C6 C1 121.89(13) . . ?
C7 N7 N8 129.71(13) . . ?
C8 N7 N8 123.72(12) . . ?
C8 N7 C7 106.46(12) . . ?
N7 N8 H8A 111.9(13) . . ?
N7 N8 H8B 107.3(15) . . ?
H8A N8 H8B 109(2) . . ?
C8 N9 N10 100.64(11) . . ?
N9 N10 H10 119.4(14) . . ?
C9 N10 N9 113.17(12) . . ?
C9 N10 H10 127.3(14) . . ?
C8 N11 N12 113.93(12) . . ?
C9 N11 N12 138.65(12) . . ?
C9 N11 C8 107.22(12) . . ?
C7 N12 N11 100.97(11) . . ?
H13A N13 H13B 116(2) . . ?
C7 N13 H13A 118.5(14) . . ?
C7 N13 H13B 119.7(14) . . ?
H14A N14 H14B 117(2) . . ?
C9 N14 H14A 118.2(14) . . ?
C9 N14 H14B 123.4(15) . . ?
N12 C7 N7 113.54(13) . . ?
N12 C7 N13 125.35(13) . . ?
N13 C7 N7 121.09(13) . . ?
N9 C8 N7 140.52(14) . . ?
N9 C8 N11 114.39(13) . . ?
N11 C8 N7 105.08(12) . . ?
N10 C9 N11 104.56(12) . . ?
N14 C9 N10 129.90(14) . . ?
N14 C9 N11 125.53(14) . . ?
C10 N15 N16 123.05(12) . . ?
C11 N15 N16 130.87(12) . . ?
C11 N15 C10 105.99(12) . . ?
N15 N16 H16A 109.2(13) . . ?
N15 N16 H16B 110.4(15) . . ?
H16A N16 H16B 111.3(19) . . ?
C11 N17 N18 100.81(11) . . ?
N17 N18 H18 121.3(15) . . ?
C12 N18 N17 113.26(12) . . ?
C12 N18 H18 124.8(15) . . ?
C11 N19 N20 114.01(12) . . ?
C12 N19 N20 138.55(12) . . ?
C12 N19 C11 107.38(12) . . ?
C10 N20 N19 100.72(11) . . ?
H21A N21 H21B 119(2) . . ?
C12 N21 H21A 119.4(14) . . ?
C12 N21 H21B 121.2(17) . . ?
H22A N22 H22B 122(2) . . ?
C10 N22 H22A 115.4(15) . . ?
C10 N22 H22B 118.2(15) . . ?
N20 C10 N15 114.06(12) . . ?
N20 C10 N22 125.58(13) . . ?
N22 C10 N15 120.30(13) . . ?
N17 C11 N15 140.75(14) . . ?
N17 C11 N19 114.08(13) . . ?
N19 C11 N15 105.16(12) . . ?
N18 C12 N19 104.47(13) . . ?
N21 C12 N18 128.45(14) . . ?
N21 C12 N19 127.07(14) . . ?

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
N8 H8B O6 0.85(2) 2.29(2) 3.0569(18) 151(2) 1_655 yes
N10 H10 O2 0.89(2) 1.90(2) 2.7701(17) 167(2) 2_767 yes
N13 H13A O1 0.90(2) 2.00(2) 2.7625(17) 141.9(19) 1_445 yes
N14 H14A N8 0.84(2) 2.22(2) 3.0459(19) 167.5(19) 1_455 yes
N14 H14B O7 0.88(2) 2.02(2) 2.9045(17) 175(2) 2_667 yes
N16 H16A N3 0.87(2) 2.22(2) 3.0827(19) 168.6(18) 1_565 yes
N16 H16B O1 0.91(3) 2.20(2) 3.0176(18) 149(2) 1_455 yes
N18 H18 O4 0.90(2) 1.92(3) 2.8077(17) 167(2) 2_556 yes
N21 H21A O3 0.92(2) 2.11(2) 3.0057(17) 165.4(19) 2_556 yes
N21 H21B O4 0.81(3) 2.28(3) 3.0769(18) 165(2) 2_656 yes
N21 H21B N3 0.81(3) 2.43(3) 3.0946(18) 140(2) 2_656 yes
N22 H22A N17 0.90(2) 2.04(2) 2.9161(18) 164(2) 1_655 yes
N22 H22B O5 0.85(2) 2.40(2) 3.0158(17) 129.1(19) 1_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
O5 N5 C4 C3 30.06(19) . . . . ?
O5 N5 C4 C5 -142.37(13) . . . . ?
O6 N5 C4 C3 -153.82(13) . . . . ?
O6 N5 C4 C5 33.74(18) . . . . ?
O7 N6 C6 C1 -143.91(13) . . . . ?
O7 N6 C6 C5 36.26(18) . . . . ?
O8 N6 C6 C1 38.47(19) . . . . ?
O8 N6 C6 C5 -141.36(13) . . . . ?
N1 C1 C2 C3 -179.45(13) . . . . ?
N1 C1 C6 N6 1.4(2) . . . . ?
N1 C1 C6 C5 -178.77(13) . . . . ?
N2 N1 C1 C2 -137.06(13) . . . . ?
N2 N1 C1 C6 47.9(2) . . . . ?
N3 C3 C4 N5 8.5(2) . . . . ?
N3 C3 C4 C5 -179.50(13) . . . . ?
N4 N3 C3 C2 -143.07(14) . . . . ?
N4 N3 C3 C4 42.3(2) . . . . ?
N5 C4 C5 C6 168.63(12) . . . . ?
C1 N1 N2 O1 -174.99(12) . . . . ?
C1 N1 N2 O2 7.4(2) . . . . ?
C1 C2 C3 N3 -177.27(13) . . . . ?
C1 C2 C3 C4 -2.0(2) . . . . ?
C2 C1 C6 N6 -173.61(12) . . . . ?
C2 C1 C6 C5 6.2(2) . . . . ?
C2 C3 C4 N5 -166.02(13) . . . . ?
C2 C3 C4 C5 6.0(2) . . . . ?
C3 N3 N4 O3 4.2(2) . . . . ?
C3 N3 N4 O4 -177.54(12) . . . . ?
C3 C4 C5 C6 -3.9(2) . . . . ?
C4 C5 C6 N6 177.35(12) . . . . ?
C4 C5 C6 C1 -2.5(2) . . . . ?
C6 C1 C2 C3 -3.9(2) . . . . ?
N8 N7 C7 N12 174.85(14) . . . . ?
N8 N7 C7 N13 -7.1(2) . . . . ?
N8 N7 C8 N9 6.6(3) . . . . ?
N8 N7 C8 N11 -174.87(13) . . . . ?
N9 N10 C9 N11 0.71(16) . . . . ?
N9 N10 C9 N14 179.36(15) . . . . ?
N10 N9 C8 N7 177.32(19) . . . . ?
N10 N9 C8 N11 -1.13(16) . . . . ?
N11 N12 C7 N7 0.45(15) . . . . ?
N11 N12 C7 N13 -177.50(14) . . . . ?
N12 N11 C8 N7 -1.48(16) . . . . ?
N12 N11 C8 N9 177.49(12) . . . . ?
N12 N11 C9 N10 -175.58(16) . . . . ?
N12 N11 C9 N14 5.7(3) . . . . ?
C7 N7 C8 N9 -176.91(19) . . . . ?
C7 N7 C8 N11 1.63(15) . . . . ?
C8 N7 C7 N12 -1.37(17) . . . . ?
C8 N7 C7 N13 176.68(13) . . . . ?
C8 N9 N10 C9 0.23(16) . . . . ?
C8 N11 N12 C7 0.65(15) . . . . ?
C8 N11 C9 N10 -1.33(16) . . . . ?
C8 N11 C9 N14 179.93(15) . . . . ?
C9 N11 N12 C7 174.64(17) . . . . ?
C9 N11 C8 N7 -177.33(12) . . . . ?
C9 N11 C8 N9 1.65(17) . . . . ?
N16 N15 C10 N20 -179.05(13) . . . . ?
N16 N15 C10 N22 -1.8(2) . . . . ?
N16 N15 C11 N17 -0.2(3) . . . . ?
N16 N15 C11 N19 178.80(14) . . . . ?
N17 N18 C12 N19 0.17(16) . . . . ?
N17 N18 C12 N21 179.26(15) . . . . ?
N18 N17 C11 N15 179.23(19) . . . . ?
N18 N17 C11 N19 0.25(16) . . . . ?
N19 N20 C10 N15 1.02(15) . . . . ?
N19 N20 C10 N22 -176.08(14) . . . . ?
N20 N19 C11 N15 -1.80(16) . . . . ?
N20 N19 C11 N17 177.53(12) . . . . ?
N20 N19 C12 N18 -176.83(16) . . . . ?
N20 N19 C12 N21 4.1(3) . . . . ?
C10 N15 C11 N17 -176.79(19) . . . . ?
C10 N15 C11 N19 2.24(15) . . . . ?
C11 N15 C10 N20 -2.15(17) . . . . ?
C11 N15 C10 N22 175.11(13) . . . . ?
C11 N17 N18 C12 -0.25(16) . . . . ?
C11 N19 N20 C10 0.51(15) . . . . ?
C11 N19 C12 N18 -0.01(16) . . . . ?
C11 N19 C12 N21 -179.12(15) . . . . ?
C12 N19 N20 C10 177.19(17) . . . . ?
C12 N19 C11 N15 -179.50(12) . . . . ?
C12 N19 C11 N17 -0.16(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 JS57F
_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 1.897
_oxdiff_exptl_absorpt_empirical_full_min 0.641
####################################################################### 
# 
# 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_js224c
_database_code_depnum_ccdc_archive 'CCDC 2345095'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2024-02-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 N8 O8, 2(C3 H7 N8), 2(H2 O)'
_chemical_formula_sum            'C10 H18 N24 O10'
_chemical_formula_weight         634.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H16N24O9
_chemical_oxdiff_usercomment     JS65-2TATOT
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.9556(6)
_cell_length_b                   5.43943(16)
_cell_length_c                   22.8384(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.712(3)
_cell_angle_gamma                90
_cell_volume                     2397.77(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8153
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.5530
_cell_measurement_theta_min      2.2900
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.0193
1 0 1 0.0193
0 -1 0 0.1223
0 1 0 0.1275
-1 0 1 0.0049
1 0 -1 0.0049

_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
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
-0.9998 -0.0000 -1.0000 0.0085 0.0634 0.0998
0.9998 0.0000 1.0000 -0.0085 -0.0634 -0.0998
-0.0043 -1.0005 0.0009 0.1813 -0.1905 0.1058
0.0043 1.0005 -0.0009 -0.1813 0.1905 -0.1058
-1.0004 0.0001 0.9995 0.0705 0.0532 -0.0246
1.0004 -0.0001 -0.9995 -0.0705 -0.0532 0.0246

_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  0.0678
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18325
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.699
_diffrn_reflns_theta_min         2.289
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  25.00   0.50    0.20    --  -47.23  94.00-171.00  204
  2  ω    -70.00 -45.00   0.50    0.80    --  -86.25  94.00-171.00   50
  3  ω    -34.00  25.00   0.50    0.20    --  -47.23  37.00 -60.00  118
  4  ω    -38.00 -12.00   0.50    0.80    --  -86.25  30.00  30.00   52
  5  ω    -37.00 -12.00   0.50    0.80    --  -86.25  30.00 120.00   50
  6  ω    -71.00 -37.00   0.50    0.20    --  -47.23 -37.00  60.00   68
  7  ω   -118.00 -80.00   0.50    0.20    --  -47.23 -37.00  60.00   76
  8  ω   -130.00-102.00   0.50    0.80    --  -86.25 -94.00  77.00   56
  9  ω     -6.00  60.00   0.50    0.20    --   47.23 -94.00  77.00  132
 10  ω     78.00 103.00   0.50    0.80    --  107.75 -94.00 120.00   50
 11  ω     65.00  91.00   0.50    0.80    --  107.75 -94.00  77.00   52
 12  ω     71.00  96.00   0.50    0.80    --  107.75-125.00-150.00   50
 13  ω     39.00  65.00   0.50    0.80    --  107.75-125.00-150.00   52
 14  ω     37.00  98.00   0.50    0.80    --  107.75 -77.00 -90.00  122
 15  ω     37.00  63.00   0.50    0.80    --  107.75 -77.00-180.00   52
 16  ω     54.00  86.00   0.50    0.80    --  107.75 -77.00 -60.00   64
 17  ω     37.00  68.00   0.50    0.80    --  107.75 -61.00-180.00   62
 18  ω     55.00  99.00   0.50    0.80    --  107.75 -77.00  90.00   88
 19  ω     36.00  97.00   0.50    0.80    --  107.75 -77.00 150.00  122
 20  ω     40.00  69.00   0.50    0.80    --  107.75 -61.00 150.00   58
 21  ω     38.00  65.00   0.50    0.80    --  107.75 -61.00  90.00   54
 22  ω     37.00  66.00   0.50    0.80    --  107.75 -61.00   0.00   58
 23  ω    -16.00  24.00   0.50    0.20    --   47.23 -19.00  60.00   80
 24  ω     43.00  68.00   0.50    0.80    --  107.75 -61.00 -90.00   50
 25  ω     35.00  60.00   0.50    0.80    --  107.75 -61.00-120.00   50
 26  ω     35.00  62.00   0.50    0.80    --  107.75 -61.00-150.00   54
 27  ω    107.00 134.00   0.50    0.80    --  107.75  61.00-120.00   54
 28  ω    115.00 175.00   0.50    0.80    --  107.75  77.00 -90.00  120
 29  ω    147.00 178.00   0.50    0.80    --  107.75  61.00-120.00   62
 30  ω    139.00 164.00   0.50    0.80    --  107.75  77.00-180.00   50
 31  ω    107.00 178.00   0.50    0.80    --  107.75  94.00-171.00  142
;
_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      -0.0395172000
_diffrn_orient_matrix_UB_12      -0.1809886000
_diffrn_orient_matrix_UB_13      0.0309804000
_diffrn_orient_matrix_UB_21      -0.0582752000
_diffrn_orient_matrix_UB_22      0.1906922000
_diffrn_orient_matrix_UB_23      -0.0050988000
_diffrn_orient_matrix_UB_31      -0.0375957000
_diffrn_orient_matrix_UB_32      -0.1055976000
_diffrn_orient_matrix_UB_33      -0.0622437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_diffrn_special_details          
'Hydrogen atoms were found by difference Fourier methods and refined isotropically.'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3887
_reflns_number_total             4958
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (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  (Sheldrick, 2015)'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.012
_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)+(0.0625P)²+1.5604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1348
_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 0.22650(9) 1.0323(4) 0.43353(8) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.12166(10) 1.0503(4) 0.44630(8) 0.0320(4) Uani 1 1 d . . . . .
O3 O 0.30803(9) 0.4973(3) 0.44649(7) 0.0284(4) Uani 1 1 d . . . . .
O4 O 0.19989(10) 0.5415(4) 0.44690(8) 0.0307(4) Uani 1 1 d . . . . .
O5 O 0.35293(9) 0.3608(3) 0.25885(7) 0.0268(4) Uani 1 1 d . . . . .
O6 O 0.26010(9) 0.3340(3) 0.18489(7) 0.0241(4) Uani 1 1 d . . . . .
O7 O 0.30490(8) 0.8117(3) 0.18413(7) 0.0229(4) Uani 1 1 d . . . . .
O8 O 0.22728(9) 0.8731(3) 0.09932(7) 0.0259(4) Uani 1 1 d . . . . .
N1 N 0.16939(10) 0.8565(4) 0.27362(9) 0.0223(4) Uani 1 1 d . . . . .
N2 N 0.26737(10) 0.5103(4) 0.32635(8) 0.0204(4) Uani 1 1 d . . . . .
N3 N 0.13406(10) 0.9143(4) 0.36032(9) 0.0254(4) Uani 1 1 d . . . . .
N4 N 0.16220(11) 0.9974(4) 0.41498(9) 0.0256(4) Uani 1 1 d . . . . .
N5 N 0.24798(11) 0.5513(4) 0.42244(9) 0.0243(4) Uani 1 1 d . . . . .
N6 N 0.29226(10) 0.4076(4) 0.23497(8) 0.0198(4) Uani 1 1 d . . . . .
N7 N 0.19053(10) 0.8195(4) 0.18100(8) 0.0205(4) Uani 1 1 d . . . . .
N8 N 0.24255(10) 0.8306(4) 0.15526(9) 0.0208(4) Uani 1 1 d . . . . .
C1 C 0.17946(11) 0.8020(4) 0.33241(10) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.23116(12) 0.6269(4) 0.35823(10) 0.0204(5) Uani 1 1 d . . . . .
C3 C 0.25474(11) 0.5622(4) 0.26845(10) 0.0188(4) Uani 1 1 d . . . . .
C4 C 0.20692(11) 0.7446(4) 0.24047(10) 0.0196(4) Uani 1 1 d . . . . .
N17 N 0.53063(10) 0.6758(4) 0.42880(8) 0.0183(4) Uani 1 1 d . . . . .
H17 H 0.5453(18) 0.808(7) 0.4505(16) 0.043(9) Uiso 1 1 d . . . . .
N18 N 0.47015(9) 0.5479(4) 0.43128(8) 0.0175(4) Uani 1 1 d . . . . .
N19 N 0.43372(9) 0.1662(3) 0.36825(8) 0.0168(4) Uani 1 1 d . . . . .
N20 N 0.52235(10) 0.1996(3) 0.32268(8) 0.0174(4) Uani 1 1 d . . . . .
N21 N 0.52335(9) 0.3842(3) 0.36578(8) 0.0162(4) Uani 1 1 d . . . . .
N22 N 0.61939(11) 0.6564(4) 0.37512(9) 0.0221(4) Uani 1 1 d . . . . .
H22A H 0.6381(15) 0.575(6) 0.3548(13) 0.024(7) Uiso 1 1 d . . . . .
H22B H 0.6406(18) 0.776(8) 0.3916(17) 0.042(10) Uiso 1 1 d . . . . .
N23 N 0.37031(10) 0.0764(4) 0.37461(9) 0.0195(4) Uani 1 1 d . . . . .
H23A H 0.3754(12) 0.027(5) 0.4113(12) 0.009(6) Uiso 1 1 d . . . . .
H23B H 0.3387(18) 0.202(7) 0.3648(15) 0.038(9) Uiso 1 1 d . . . . .
N24 N 0.44242(11) -0.1289(4) 0.29487(9) 0.0189(4) Uani 1 1 d . . . . .
H24A H 0.4583(13) -0.163(5) 0.2656(13) 0.014(6) Uiso 1 1 d . . . . .
H24B H 0.4006(16) -0.170(6) 0.2952(13) 0.023(7) Uiso 1 1 d . . . . .
C8 C 0.56308(11) 0.5791(4) 0.38929(9) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.46976(11) 0.3726(4) 0.39204(9) 0.0157(4) Uani 1 1 d . . . . .
C11 C 0.46652(11) 0.0749(4) 0.32595(9) 0.0171(4) Uani 1 1 d . . . . .
N9 N 0.10336(11) 0.2696(4) 0.15822(9) 0.0241(4) Uani 1 1 d . . . . .
H9 H 0.1255(16) 0.135(6) 0.1727(14) 0.031(8) Uiso 1 1 d . . . . .
N10 N 0.06342(11) 0.4005(4) 0.18986(9) 0.0242(4) Uani 1 1 d . . . . .
N11 N -0.00023(10) 0.7821(4) 0.14530(8) 0.0224(4) Uani 1 1 d . . . . .
N12 N 0.03527(10) 0.7525(4) 0.05839(8) 0.0211(4) Uani 1 1 d . . . . .
N13 N 0.06086(10) 0.5608(4) 0.09940(8) 0.0197(4) Uani 1 1 d . . . . .
N14 N 0.13466(11) 0.2814(4) 0.06392(10) 0.0268(5) Uani 1 1 d . . . . .
H14A H 0.1311(16) 0.356(6) 0.0285(15) 0.031(8) Uiso 1 1 d . . . . .
H14B H 0.1600(18) 0.147(7) 0.0697(15) 0.038(9) Uiso 1 1 d . . . . .
N15 N -0.04264(13) 0.8630(4) 0.18140(10) 0.0288(5) Uani 1 1 d . . . . .
H15A H -0.0670(18) 0.733(7) 0.1916(16) 0.040(9) Uiso 1 1 d . . . . .
H15B H -0.0154(19) 0.905(7) 0.2161(18) 0.047(10) Uiso 1 1 d . . . . .
N16 N -0.03852(11) 1.0814(4) 0.06934(10) 0.0236(4) Uani 1 1 d . . . . .
H16A H -0.0428(16) 1.137(6) 0.0328(15) 0.028(8) Uiso 1 1 d . . . . .
H16B H -0.065(2) 1.128(7) 0.0915(17) 0.050(11) Uiso 1 1 d . . . . .
C5 C 0.10245(12) 0.3638(4) 0.10380(10) 0.0209(5) Uani 1 1 d . . . . .
C6 C 0.03970(12) 0.5754(5) 0.15092(10) 0.0216(5) Uani 1 1 d . . . . .
C7 C -0.00249(12) 0.8771(4) 0.08836(10) 0.0208(5) Uani 1 1 d . . . . .
O2W O 0.41931(9) 0.8969(3) 0.50564(7) 0.0210(3) Uani 1 1 d . . . . .
H2WA H 0.3804(17) 0.886(6) 0.5202(15) 0.035(8) Uiso 1 1 d . . . . .
H2WB H 0.4261(18) 0.772(7) 0.4880(16) 0.042(10) Uiso 1 1 d . . . . .
O1W O 0.30705(10) 0.9555(4) 0.54988(9) 0.0259(4) Uani 1 1 d . . . . .
H1WA H 0.288(2) 0.857(8) 0.5658(18) 0.051(11) Uiso 1 1 d . . . . .
H1WB H 0.278(2) 0.998(8) 0.523(2) 0.056(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 N4 1.259(3) . ?
O2 N4 1.242(3) . ?
O3 N5 1.221(3) . ?
O4 N5 1.228(3) . ?
O5 N6 1.222(3) . ?
O6 N6 1.228(3) . ?
O7 N8 1.256(2) . ?
O8 N8 1.257(3) . ?
N1 C1 1.339(3) . ?
N1 C4 1.339(3) . ?
N2 C2 1.312(3) . ?
N2 C3 1.312(3) . ?
N3 N4 1.312(3) . ?
N3 C1 1.376(3) . ?
N5 C2 1.477(3) . ?
N6 C3 1.464(3) . ?
N7 N8 1.318(3) . ?
N7 C4 1.375(3) . ?
C1 C2 1.418(3) . ?
C3 C4 1.412(3) . ?
N17 H17 0.88(4) . ?
N17 N18 1.406(3) . ?
N17 C8 1.344(3) . ?
N18 C10 1.307(3) . ?
N19 N23 1.398(3) . ?
N19 C10 1.369(3) . ?
N19 C11 1.389(3) . ?
N20 N21 1.403(2) . ?
N20 C11 1.322(3) . ?
N21 C8 1.351(3) . ?
N21 C10 1.354(3) . ?
N22 H22A 0.80(3) . ?
N22 H22B 0.81(4) . ?
N22 C8 1.315(3) . ?
N23 H23A 0.86(3) . ?
N23 H23B 0.92(4) . ?
N24 H24A 0.83(3) . ?
N24 H24B 0.86(3) . ?
N24 C11 1.338(3) . ?
N9 H9 0.88(3) . ?
N9 N10 1.399(3) . ?
N9 C5 1.340(3) . ?
N10 C6 1.306(3) . ?
N11 N15 1.394(3) . ?
N11 C6 1.365(3) . ?
N11 C7 1.389(3) . ?
N12 N13 1.408(3) . ?
N12 C7 1.326(3) . ?
N13 C5 1.343(3) . ?
N13 C6 1.350(3) . ?
N14 H14A 0.89(3) . ?
N14 H14B 0.88(4) . ?
N14 C5 1.319(3) . ?
N15 H15A 0.92(4) . ?
N15 H15B 0.87(4) . ?
N16 H16A 0.87(3) . ?
N16 H16B 0.86(4) . ?
N16 C7 1.335(3) . ?
O2W H2WA 0.92(4) . ?
O2W H2WB 0.82(4) . ?
O1W H1WA 0.80(5) . ?
O1W H1WB 0.76(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 120.2(2) . . ?
C2 N2 C3 117.6(2) . . ?
N4 N3 C1 114.86(19) . . ?
O1 N4 N3 121.7(2) . . ?
O2 N4 O1 121.9(2) . . ?
O2 N4 N3 116.3(2) . . ?
O3 N5 O4 125.2(2) . . ?
O3 N5 C2 117.6(2) . . ?
O4 N5 C2 117.18(19) . . ?
O5 N6 O6 124.9(2) . . ?
O5 N6 C3 117.83(18) . . ?
O6 N6 C3 117.27(18) . . ?
N8 N7 C4 115.94(18) . . ?
O7 N8 O8 120.1(2) . . ?
O7 N8 N7 123.34(18) . . ?
O8 N8 N7 116.53(18) . . ?
N1 C1 N3 114.6(2) . . ?
N1 C1 C2 118.3(2) . . ?
N3 C1 C2 126.9(2) . . ?
N2 C2 N5 113.5(2) . . ?
N2 C2 C1 122.6(2) . . ?
C1 C2 N5 123.9(2) . . ?
N2 C3 N6 114.22(19) . . ?
N2 C3 C4 122.8(2) . . ?
C4 C3 N6 122.93(19) . . ?
N1 C4 N7 113.4(2) . . ?
N1 C4 C3 118.3(2) . . ?
N7 C4 C3 128.2(2) . . ?
N18 N17 H17 123(2) . . ?
C8 N17 H17 123(2) . . ?
C8 N17 N18 113.45(18) . . ?
C10 N18 N17 100.89(18) . . ?
C10 N19 N23 130.05(18) . . ?
C10 N19 C11 106.03(18) . . ?
C11 N19 N23 123.11(18) . . ?
C11 N20 N21 100.93(17) . . ?
C8 N21 N20 138.00(19) . . ?
C8 N21 C10 108.07(18) . . ?
C10 N21 N20 113.93(18) . . ?
H22A N22 H22B 117(3) . . ?
C8 N22 H22A 121(2) . . ?
C8 N22 H22B 121(3) . . ?
N19 N23 H23A 108.9(16) . . ?
N19 N23 H23B 107(2) . . ?
H23A N23 H23B 112(3) . . ?
H24A N24 H24B 121(3) . . ?
C11 N24 H24A 116.9(19) . . ?
C11 N24 H24B 115(2) . . ?
N17 C8 N21 103.87(19) . . ?
N22 C8 N17 128.9(2) . . ?
N22 C8 N21 127.2(2) . . ?
N18 C10 N19 141.4(2) . . ?
N18 C10 N21 113.7(2) . . ?
N21 C10 N19 104.87(18) . . ?
N20 C11 N19 114.11(19) . . ?
N20 C11 N24 126.1(2) . . ?
N24 C11 N19 119.7(2) . . ?
N10 N9 H9 122(2) . . ?
C5 N9 H9 124(2) . . ?
C5 N9 N10 114.2(2) . . ?
C6 N10 N9 100.04(19) . . ?
C6 N11 N15 129.2(2) . . ?
C6 N11 C7 105.89(19) . . ?
C7 N11 N15 123.8(2) . . ?
C7 N12 N13 101.12(18) . . ?
C5 N13 N12 138.9(2) . . ?
C5 N13 C6 107.82(19) . . ?
C6 N13 N12 113.29(19) . . ?
H14A N14 H14B 115(3) . . ?
C5 N14 H14A 122(2) . . ?
C5 N14 H14B 123(2) . . ?
N11 N15 H15A 110(2) . . ?
N11 N15 H15B 107(3) . . ?
H15A N15 H15B 103(3) . . ?
H16A N16 H16B 123(3) . . ?
C7 N16 H16A 121(2) . . ?
C7 N16 H16B 115(3) . . ?
N9 C5 N13 103.7(2) . . ?
N14 C5 N9 128.0(2) . . ?
N14 C5 N13 128.3(2) . . ?
N10 C6 N11 140.0(2) . . ?
N10 C6 N13 114.3(2) . . ?
N13 C6 N11 105.72(19) . . ?
N12 C7 N11 113.9(2) . . ?
N12 C7 N16 126.0(2) . . ?
N16 C7 N11 120.1(2) . . ?
H2WA O2W H2WB 113(3) . . ?
H1WA O1W H1WB 102(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
N17 H17 O2W 0.88(4) 1.93(4) 2.808(3) 176(4) 3_676 yes
N22 H22A O7 0.80(3) 2.16(3) 2.944(3) 169(3) 2_645 yes
N22 H22B O1W 0.81(4) 2.07(4) 2.875(3) 168(4) 3_676 yes
N23 H23A O2W 0.86(3) 2.23(3) 3.062(3) 164(2) 1_545 yes
N24 H24A N20 0.83(3) 2.27(3) 3.087(3) 167(2) 2_645 yes
N9 H9 N7 0.88(3) 2.13(3) 2.972(3) 161(3) 1_545 yes
N14 H14A O2 0.89(3) 1.91(3) 2.787(3) 168(3) 4_575 yes
N14 H14B O8 0.88(4) 2.00(4) 2.871(3) 168(3) 1_545 yes
N15 H15A N3 0.92(4) 2.32(4) 3.051(3) 136(3) 2_545 yes
N15 H15B N10 0.87(4) 2.56(4) 3.078(3) 119(3) 2 yes
N16 H16A N12 0.87(3) 2.21(3) 3.070(3) 170(3) 3_575 yes
N16 H16B O2 0.86(4) 2.61(4) 3.014(3) 110(3) 2 yes
O2W H2WA O1W 0.92(4) 1.80(4) 2.700(3) 164(3) . yes
O2W H2WB N18 0.82(4) 2.12(4) 2.897(3) 157(3) . yes
O1W H1WA O8 0.80(5) 2.02(5) 2.814(3) 173(4) 4_576 yes
O1W H1WB O1 0.76(4) 2.06(4) 2.766(3) 156(4) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 N5 C2 N2 34.9(3) . . . . ?
O3 N5 C2 C1 -147.1(2) . . . . ?
O4 N5 C2 N2 -143.3(2) . . . . ?
O4 N5 C2 C1 34.7(3) . . . . ?
O5 N6 C3 N2 -41.8(3) . . . . ?
O5 N6 C3 C4 140.6(2) . . . . ?
O6 N6 C3 N2 137.9(2) . . . . ?
O6 N6 C3 C4 -39.6(3) . . . . ?
N1 C1 C2 N2 -2.7(3) . . . . ?
N1 C1 C2 N5 179.5(2) . . . . ?
N2 C3 C4 N1 -4.9(3) . . . . ?
N2 C3 C4 N7 178.3(2) . . . . ?
N3 C1 C2 N2 172.7(2) . . . . ?
N3 C1 C2 N5 -5.1(4) . . . . ?
N4 N3 C1 N1 -138.9(2) . . . . ?
N4 N3 C1 C2 45.6(3) . . . . ?
N6 C3 C4 N1 172.4(2) . . . . ?
N6 C3 C4 N7 -4.4(4) . . . . ?
N8 N7 C4 N1 144.8(2) . . . . ?
N8 N7 C4 C3 -38.2(3) . . . . ?
C1 N1 C4 N7 179.9(2) . . . . ?
C1 N1 C4 C3 2.6(3) . . . . ?
C1 N3 N4 O1 18.4(3) . . . . ?
C1 N3 N4 O2 -164.8(2) . . . . ?
C2 N2 C3 N6 -174.28(19) . . . . ?
C2 N2 C3 C4 3.3(3) . . . . ?
C3 N2 C2 N5 178.6(2) . . . . ?
C3 N2 C2 C1 0.5(3) . . . . ?
C4 N1 C1 N3 -175.0(2) . . . . ?
C4 N1 C1 C2 0.9(3) . . . . ?
C4 N7 N8 O7 -10.5(3) . . . . ?
C4 N7 N8 O8 172.61(19) . . . . ?
N17 N18 C10 N19 176.2(3) . . . . ?
N17 N18 C10 N21 -0.7(2) . . . . ?
N18 N17 C8 N21 -0.3(2) . . . . ?
N18 N17 C8 N22 178.3(2) . . . . ?
N20 N21 C8 N17 178.9(2) . . . . ?
N20 N21 C8 N22 0.3(4) . . . . ?
N20 N21 C10 N18 -178.70(17) . . . . ?
N20 N21 C10 N19 3.3(2) . . . . ?
N21 N20 C11 N19 -0.9(2) . . . . ?
N21 N20 C11 N24 -177.9(2) . . . . ?
N23 N19 C10 N18 9.6(4) . . . . ?
N23 N19 C10 N21 -173.26(19) . . . . ?
N23 N19 C11 N20 173.51(18) . . . . ?
N23 N19 C11 N24 -9.3(3) . . . . ?
C8 N17 N18 C10 0.6(2) . . . . ?
C8 N21 C10 N18 0.6(2) . . . . ?
C8 N21 C10 N19 -177.40(17) . . . . ?
C10 N19 C11 N20 2.9(2) . . . . ?
C10 N19 C11 N24 -179.93(18) . . . . ?
C10 N21 C8 N17 -0.2(2) . . . . ?
C10 N21 C8 N22 -178.8(2) . . . . ?
C11 N19 C10 N18 179.4(3) . . . . ?
C11 N19 C10 N21 -3.5(2) . . . . ?
C11 N20 N21 C8 179.4(2) . . . . ?
C11 N20 N21 C10 -1.5(2) . . . . ?
N9 N10 C6 N11 -177.4(3) . . . . ?
N9 N10 C6 N13 0.5(3) . . . . ?
N10 N9 C5 N13 -0.1(3) . . . . ?
N10 N9 C5 N14 -179.9(2) . . . . ?
N12 N13 C5 N9 178.6(2) . . . . ?
N12 N13 C5 N14 -1.6(5) . . . . ?
N12 N13 C6 N10 -179.37(19) . . . . ?
N12 N13 C6 N11 -0.8(3) . . . . ?
N13 N12 C7 N11 2.1(2) . . . . ?
N13 N12 C7 N16 179.7(2) . . . . ?
N15 N11 C6 N10 -12.2(5) . . . . ?
N15 N11 C6 N13 169.8(2) . . . . ?
N15 N11 C7 N12 -171.3(2) . . . . ?
N15 N11 C7 N16 10.9(3) . . . . ?
C5 N9 N10 C6 -0.2(3) . . . . ?
C5 N13 C6 N10 -0.7(3) . . . . ?
C5 N13 C6 N11 177.92(19) . . . . ?
C6 N11 C7 N12 -2.7(3) . . . . ?
C6 N11 C7 N16 179.6(2) . . . . ?
C6 N13 C5 N9 0.5(2) . . . . ?
C6 N13 C5 N14 -179.8(2) . . . . ?
C7 N11 C6 N10 179.9(3) . . . . ?
C7 N11 C6 N13 1.9(2) . . . . ?
C7 N12 N13 C5 -178.9(3) . . . . ?
C7 N12 N13 C6 -0.8(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 JS65-2TATOT
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.673
_vrf_PLAT430_js224c              
;
PROBLEM: Short Inter D...A Contact  O5       ..N19      .       2.81 Ang.  
RESPONSE: We have seen in these small compounds that they will pack with some 
relatively short O---N distances that get flagged by cifcheck routine.
;
####################################################################### 
# 
# 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_js1222c
_database_code_depnum_ccdc_archive 'CCDC 2345099'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2022-12-16
_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 N7 O4, C3 H7 N8, H O0.5'
_chemical_formula_sum            'C6 H8 N15 O4.50'
_chemical_formula_weight         362.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H7N15O4
_chemical_oxdiff_usercomment     JS500F
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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   21.7598(3)
_cell_length_b                   6.30828(8)
_cell_length_c                   19.7952(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2717.24(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7503
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.7030
_cell_measurement_theta_min      4.0540
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.774
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (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_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0868
0 0 -1 0.0686
0 1 0 0.1068
0 -1 0 0.0957
-1 0 0 0.0153
1 0 0 0.0153

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.031
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
0.0001 0.0001 0.9990 -0.0120 0.0447 -0.0625
-0.0001 -0.0001 -0.9990 0.0120 -0.0447 0.0625
-0.0008 0.9992 -0.0004 -0.1821 0.1135 0.1163
0.0008 -0.9992 0.0004 0.1821 -0.1135 -0.1163
-0.9991 0.0001 0.0001 0.0458 0.0476 0.0253
0.9991 -0.0001 -0.0001 -0.0458 -0.0476 -0.0253

_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10609
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.047
_diffrn_reflns_theta_min         4.063
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(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 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  18.00   0.50    0.18    --  -48.74  48.00 178.00  134
  2  ω    -50.00 -14.00   0.50    0.71    --  -86.25  45.00 120.00   72
  3  ω    -51.00 -26.00   0.50    0.71    --  -86.25  45.00-120.00   50
  4  ω    -44.00 -17.00   0.50    0.71    --  -86.25  45.00-150.00   54
  5  ω    -17.00  26.00   0.50    0.18    --  -48.74  19.00 -60.00   86
  6  ω   -109.00 -19.00   0.50    0.71    --  -86.25  84.00  28.00  180
  7  ω   -111.00 -85.00   0.50    0.18    --  -48.74-125.00-180.00   52
  8  ω     40.00  65.00   0.50    0.71    --  107.75 -61.00  30.00   50
  9  ω     35.00 104.00   0.50    0.71    --  107.75 -95.00 171.00  138
 10  ω     36.00  62.00   0.50    0.71    --  107.75 -61.00   0.00   52
 11  ω     64.00  99.00   0.50    0.71    --  107.75 -94.00-120.00   70
 12  ω     41.00  66.00   0.50    0.71    --  107.75 -61.00-150.00   50
 13  ω    117.00 177.00   0.50    0.71    --  107.75 125.00 -30.00  120
 14  ω    108.00 150.00   0.50    0.71    --  107.75  48.00 178.00   84
;
_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      -0.0458402000
_diffrn_orient_matrix_UB_12      -0.1822736000
_diffrn_orient_matrix_UB_13      -0.0120296000
_diffrn_orient_matrix_UB_21      -0.0476412000
_diffrn_orient_matrix_UB_22      0.1135764000
_diffrn_orient_matrix_UB_23      0.0447512000
_diffrn_orient_matrix_UB_31      -0.0252868000
_diffrn_orient_matrix_UB_32      0.1163187000
_diffrn_orient_matrix_UB_33      -0.0625327000
_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                2506
_reflns_number_total             2743
_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 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (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         0.297
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.057
_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)+(0.0449P)²+1.6906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0950
_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 0.37172(5) 0.13211(19) 0.21647(6) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.32191(5) 0.01252(17) 0.12894(5) 0.0199(2) Uani 1 1 d . . . . .
O3 O 0.08610(5) 0.13580(19) 0.31803(5) 0.0246(3) Uani 1 1 d . . . . .
O4 O 0.07552(5) 0.1013(2) 0.20955(6) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.26657(5) 0.16799(19) 0.28727(6) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.20799(5) 0.17414(18) 0.30704(6) 0.0150(3) Uani 1 1 d . . . . .
N3 N 0.18401(6) 0.0227(2) 0.13248(6) 0.0165(3) Uani 1 1 d . . . . .
N4 N 0.21028(6) 0.09331(19) 0.08082(6) 0.0174(3) Uani 1 1 d . . . . .
N5 N 0.22814(7) 0.1430(2) 0.02996(7) 0.0253(3) Uani 1 1 d . . . . .
N6 N 0.32386(6) 0.08597(19) 0.18697(6) 0.0164(3) Uani 1 1 d . . . . .
N7 N 0.10730(6) 0.12196(19) 0.26069(6) 0.0166(3) Uani 1 1 d . . . . .
C1 C 0.26676(6) 0.1151(2) 0.22092(7) 0.0146(3) Uani 1 1 d . . . . .
C2 C 0.20730(6) 0.0894(2) 0.19527(7) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.17264(7) 0.1275(2) 0.25297(7) 0.0144(3) Uani 1 1 d . . . . .
N8 N 0.43753(5) -0.17118(19) 0.55874(6) 0.0158(3) Uani 1 1 d . . . . .
N9 N 0.45568(7) -0.3536(2) 0.59327(7) 0.0215(3) Uani 1 1 d . . . . .
H9A H 0.4221(11) -0.399(4) 0.6156(11) 0.037(6) Uiso 1 1 d . . . . .
H9B H 0.4683(11) -0.443(4) 0.5638(12) 0.037(6) Uiso 1 1 d . . . . .
N10 N 0.43582(6) 0.1795(2) 0.53288(6) 0.0176(3) Uani 1 1 d . . . . .
N11 N 0.39808(6) 0.05700(19) 0.49026(6) 0.0156(3) Uani 1 1 d . . . . .
N12 N 0.34405(6) -0.1149(2) 0.41967(6) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.3238(10) -0.157(4) 0.3830(11) 0.033(5) Uiso 1 1 d . . . . .
N13 N 0.36744(6) -0.2704(2) 0.46365(6) 0.0183(3) Uani 1 1 d . . . . .
N14 N 0.35341(6) 0.2586(2) 0.39972(7) 0.0211(3) Uani 1 1 d . . . . .
H14A H 0.3304(10) 0.255(4) 0.3613(12) 0.037(6) Uiso 1 1 d . . . . .
H14B H 0.3629(10) 0.373(4) 0.4182(11) 0.030(5) Uiso 1 1 d . . . . .
N15 N 0.49854(6) 0.0615(2) 0.62344(7) 0.0211(3) Uani 1 1 d . . . . .
H15A H 0.5011(10) -0.037(4) 0.6534(11) 0.035(6) Uiso 1 1 d . . . . .
H15B H 0.5030(11) 0.192(4) 0.6383(12) 0.041(6) Uiso 1 1 d . . . . .
C4 C 0.45793(6) 0.0313(2) 0.57382(7) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.36385(7) 0.0816(2) 0.43372(7) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.39913(7) -0.1525(2) 0.50466(7) 0.0160(3) Uani 1 1 d . . . . .
O5 O 0.500000 0.1962(3) 0.250000 0.0321(4) Uani 1 2 d S T P . .
H5 H 0.465(3) 0.303(10) 0.237(3) 0.21(3) 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 N6 1.2289(16) . ?
O2 N6 1.2394(16) . ?
O3 N7 1.2284(16) . ?
O4 N7 1.2328(16) . ?
N1 N2 1.3340(17) . ?
N1 C1 1.3550(19) . ?
N2 C3 1.3504(18) . ?
N3 N4 1.2533(17) . ?
N3 C2 1.4065(18) . ?
N4 N5 1.1238(18) . ?
N6 C1 1.4246(18) . ?
N7 C3 1.4305(19) . ?
C1 C2 1.3994(19) . ?
C2 C3 1.3896(19) . ?
N8 N9 1.3957(17) . ?
N8 C4 1.3848(19) . ?
N8 C6 1.3630(19) . ?
N9 H9A 0.90(2) . ?
N9 H9B 0.86(2) . ?
N10 N11 1.4083(16) . ?
N10 C4 1.327(2) . ?
N11 C5 1.3535(18) . ?
N11 C6 1.3523(19) . ?
N12 H12 0.89(2) . ?
N12 N13 1.4071(18) . ?
N12 C5 1.3410(19) . ?
N13 C6 1.2991(19) . ?
N14 H14A 0.91(2) . ?
N14 H14B 0.84(2) . ?
N14 C5 1.324(2) . ?
N15 H15A 0.86(2) . ?
N15 H15B 0.88(3) . ?
N15 C4 1.3349(19) . ?
O5 H5 1.04(6) . ?

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 107.12(11) . . ?
N1 N2 C3 107.78(11) . . ?
N4 N3 C2 116.78(12) . . ?
N5 N4 N3 171.05(15) . . ?
O1 N6 O2 123.92(12) . . ?
O1 N6 C1 118.97(12) . . ?
O2 N6 C1 117.11(12) . . ?
O3 N7 O4 123.75(12) . . ?
O3 N7 C3 118.05(12) . . ?
O4 N7 C3 118.19(12) . . ?
N1 C1 N6 119.45(12) . . ?
N1 C1 C2 112.18(12) . . ?
C2 C1 N6 128.34(13) . . ?
C1 C2 N3 133.50(13) . . ?
C3 C2 N3 125.63(13) . . ?
C3 C2 C1 100.57(12) . . ?
N2 C3 N7 119.13(12) . . ?
N2 C3 C2 112.34(12) . . ?
C2 C3 N7 128.53(13) . . ?
C4 N8 N9 124.36(12) . . ?
C6 N8 N9 129.00(12) . . ?
C6 N8 C4 106.62(12) . . ?
N8 N9 H9A 105.8(15) . . ?
N8 N9 H9B 107.4(15) . . ?
H9A N9 H9B 113(2) . . ?
C4 N10 N11 100.98(11) . . ?
C5 N11 N10 138.90(12) . . ?
C6 N11 N10 113.59(12) . . ?
C6 N11 C5 107.19(12) . . ?
N13 N12 H12 118.5(14) . . ?
C5 N12 H12 127.1(14) . . ?
C5 N12 N13 113.57(12) . . ?
C6 N13 N12 100.34(12) . . ?
H14A N14 H14B 122(2) . . ?
C5 N14 H14A 119.8(15) . . ?
C5 N14 H14B 117.8(14) . . ?
H15A N15 H15B 116(2) . . ?
C4 N15 H15A 116.6(15) . . ?
C4 N15 H15B 117.0(15) . . ?
N10 C4 N8 113.70(12) . . ?
N10 C4 N15 126.06(14) . . ?
N15 C4 N8 120.16(13) . . ?
N12 C5 N11 104.03(12) . . ?
N14 C5 N11 127.71(14) . . ?
N14 C5 N12 128.25(14) . . ?
N11 C6 N8 105.09(12) . . ?
N13 C6 N8 140.06(14) . . ?
N13 C6 N11 114.76(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9A O4 0.90(2) 2.26(2) 2.8636(18) 124.4(18) 2_545 yes
N12 H12 N2 0.89(2) 1.97(2) 2.8329(17) 163(2) 7_655 yes
N14 H14A N1 0.91(2) 2.09(2) 2.9753(18) 163(2) . yes
N15 H15A O5 0.86(2) 2.16(2) 2.9868(18) 161(2) 5_656 yes
N15 H15B O3 0.88(3) 2.28(2) 2.9358(17) 131(2) 3_556 yes
O5 H5 O1 1.04(6) 2.34(6) 2.8976(11) 112(4) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N6 C1 N1 -8.0(2) . . . . ?
O1 N6 C1 C2 174.42(14) . . . . ?
O2 N6 C1 N1 171.31(12) . . . . ?
O2 N6 C1 C2 -6.3(2) . . . . ?
O3 N7 C3 N2 -8.29(19) . . . . ?
O3 N7 C3 C2 171.45(13) . . . . ?
O4 N7 C3 N2 172.47(13) . . . . ?
O4 N7 C3 C2 -7.8(2) . . . . ?
N1 N2 C3 N7 179.60(11) . . . . ?
N1 N2 C3 C2 -0.18(16) . . . . ?
N1 C1 C2 N3 -175.02(14) . . . . ?
N1 C1 C2 C3 -1.24(15) . . . . ?
N2 N1 C1 N6 -176.78(12) . . . . ?
N2 N1 C1 C2 1.21(16) . . . . ?
N3 C2 C3 N2 175.30(13) . . . . ?
N3 C2 C3 N7 -4.5(2) . . . . ?
N4 N3 C2 C1 -42.6(2) . . . . ?
N4 N3 C2 C3 144.97(14) . . . . ?
N6 C1 C2 N3 2.7(3) . . . . ?
N6 C1 C2 C3 176.53(14) . . . . ?
C1 N1 N2 C3 -0.62(14) . . . . ?
C1 C2 C3 N2 0.84(15) . . . . ?
C1 C2 C3 N7 -178.91(14) . . . . ?
N9 N8 C4 N10 178.11(13) . . . . ?
N9 N8 C4 N15 1.3(2) . . . . ?
N9 N8 C6 N11 -178.86(13) . . . . ?
N9 N8 C6 N13 -2.7(3) . . . . ?
N10 N11 C5 N12 175.55(15) . . . . ?
N10 N11 C5 N14 -3.4(3) . . . . ?
N10 N11 C6 N8 0.99(16) . . . . ?
N10 N11 C6 N13 -176.27(12) . . . . ?
N11 N10 C4 N8 1.06(15) . . . . ?
N11 N10 C4 N15 177.64(14) . . . . ?
N12 N13 C6 N8 -176.40(18) . . . . ?
N12 N13 C6 N11 -0.53(16) . . . . ?
N13 N12 C5 N11 -3.44(16) . . . . ?
N13 N12 C5 N14 175.49(14) . . . . ?
C4 N8 C6 N11 -0.28(15) . . . . ?
C4 N8 C6 N13 175.84(18) . . . . ?
C4 N10 N11 C5 -173.63(16) . . . . ?
C4 N10 N11 C6 -1.27(15) . . . . ?
C5 N11 C6 N8 175.74(11) . . . . ?
C5 N11 C6 N13 -1.51(17) . . . . ?
C5 N12 N13 C6 2.51(16) . . . . ?
C6 N8 C4 N10 -0.55(16) . . . . ?
C6 N8 C4 N15 -177.35(13) . . . . ?
C6 N11 C5 N12 2.88(15) . . . . ?
C6 N11 C5 N14 -176.06(15) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JS500F
_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.881
####################################################################### 
# 
# 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_js1223an
_database_code_depnum_ccdc_archive 'CCDC 2345098'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C3 H6 N8), C2 N10'
_chemical_formula_sum            'C8 H12 N26'
_chemical_formula_weight         472.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H2N6O2
_chemical_oxdiff_usercomment     'JS891 Vial 1 Needles'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5508(8)
_cell_length_b                   6.7141(8)
_cell_length_c                   11.4242(9)
_cell_angle_alpha                89.787(8)
_cell_angle_beta                 78.702(9)
_cell_angle_gamma                72.292(11)
_cell_volume                     468.54(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    978
_cell_measurement_temperature    100.00(14)
_cell_measurement_theta_max      77.5790
_cell_measurement_theta_min      7.2360
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.864
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.96a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             242
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -4 -1 0.0575
-1 0 -7 0.0162
1 4 -1 0.0636
1 0 7 0.0119
-3 -1 4 0.0128
-3 2 -5 0.0293
3 1 -4 0.0056
-1 0 -2 0.0162

_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.021
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.6647 -4.3189 -0.9083 0.1241 0.9384 0.3225
-1.3445 -0.1063 -7.3757 0.0592 0.4588 -0.8866
1.3141 4.3125 -1.0569 -0.1089 -0.8207 -0.5609
1.3583 0.1472 7.3733 -0.0603 -0.4670 0.8822
-3.1433 -0.6186 3.7231 0.8908 -0.1179 0.4389
-2.5848 1.7070 -4.9062 0.5720 -0.0744 -0.8169
2.9722 0.7571 -4.1395 -0.8548 0.1132 -0.5065
-0.9962 0.0001 -2.0040 0.1765 0.1144 -0.2574

_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  0.0405
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4728
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.534
_diffrn_reflns_theta_min         6.935
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00   4.00   0.50    0.60    --  -46.86  41.00-162.00   50
  2  ω   -117.00 -58.00   0.50    0.60    --  -46.86 -41.00  44.00  118
  3  ω    -23.00  44.00   0.50    0.60    --   46.86 -41.00  44.00  134
  4  ω     37.00 106.00   0.50    0.60    --   46.86  41.00-162.00  138
  5  ω   -145.00-119.00   0.50    2.40    --  -86.25 -41.00  44.00   52
  6  ω    -43.00 -18.00   0.50    2.40    --  -86.25  41.00-162.00   50
  7  ω     97.00 158.00   0.50    2.40    --  107.75  41.00-162.00  122
  8  ω    -44.00 -16.00   0.50    0.60    --  -46.86 125.00-120.00   56
  9  ω    -74.00 -47.00   0.50    0.60    --  -46.86 125.00-120.00   54
 10  ω    -20.00  20.00   0.50    0.60    --   46.86 -19.00 -90.00   80
 11  ω     37.00  93.00   0.50    0.60    --   46.86-125.00  90.00  112
 12  ω      1.00  31.00   0.50    0.60    --   46.86 -99.00  30.00   60
 13  ω     43.00  73.00   0.50    0.60    --   46.86 -99.00  30.00   60
 14  ω   -146.00-110.00   0.50    2.40    --  -86.25 -77.00-180.00   72
 15  ω     65.00 100.00   0.50    2.40    --  107.75 -77.00  60.00   70
 16  ω    135.00 178.00   0.50    2.40    --  107.75  77.00-120.00   86
 17  ω     35.00  61.00   0.50    2.40    --  107.75 -94.00  30.00   52
 18  ω     35.00  66.00   0.50    2.40    --  107.75 -94.00   0.00   62
 19  ω     69.00  94.00   0.50    2.40    --  107.75 -94.00   0.00   50
 20  ω     50.00 103.00   0.50    2.40    --  107.75 -94.00 150.00  106
 21  ω    146.00 171.00   0.50    2.40    --  107.75  77.00  30.00   50
 22  ω     59.00 103.00   0.50    2.40    --  107.75 -94.00 -90.00   88
 23  ω     96.00 129.00   0.50    2.40    --  107.75  15.00  90.00   66
 24  ω    118.00 149.00   0.50    2.40    --  107.75  77.00 -60.00   62
 25  ω     70.00 101.00   0.50    2.40    --  107.75 -94.00-150.00   62
 26  ω     39.00  64.00   0.50    2.40    --  107.75 -94.00-150.00   50
 27  ω    144.00 169.00   0.50    2.40    --  107.75  15.00  90.00   50
 28  ω     71.00  99.00   0.50    2.40    --  107.75 -94.00-120.00   56
 29  ω    101.00 168.00   0.50    2.40    --  107.75  15.00-180.00  134
 30  ω     64.00 101.00   0.50    2.40    --  107.75 -94.00 -30.00   74
 31  ω     39.00  65.00   0.50    2.40    --  107.75 -61.00 120.00   52
 32  ω     47.00  87.00   0.50    2.40    --  107.75 -94.00  60.00   80
 33  ω     74.00 100.00   0.50    2.40    --  107.75 -94.00-180.00   52
 34  ω    109.00 135.00   0.50    2.40    --  107.75  15.00  60.00   52
 35  ω    143.00 176.00   0.50    2.40    --  107.75  15.00  60.00   66
 36  ω     38.00  66.00   0.50    2.40    --  107.75 -94.00 120.00   56
 37  ω     79.00 104.00   0.50    2.40    --  107.75 -94.00 120.00   50
 38  ω     82.00 108.00   0.50    2.40    --  107.75-125.00 150.00   52
 39  ω     35.00  64.00   0.50    2.40    --  107.75 -94.00-120.00   58
 40  ω     41.00  66.00   0.50    2.40    --  107.75 -61.00-120.00   50
 41  ω     36.00  61.00   0.50    2.40    --  107.75 -61.00   0.00   50
 42  ω     78.00 104.00   0.50    2.40    --  107.75 -94.00  30.00   52
 43  ω     37.00  62.00   0.50    2.40    --  107.75 -61.00  60.00   50
 44  ω     75.00 101.00   0.50    2.40    --  107.75 -77.00 -30.00   52
 45  ω     97.00 160.00   0.50    2.40    --  107.75 125.00  60.00  126
;
_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      -0.2515075000
_diffrn_orient_matrix_UB_12      0.0604414000
_diffrn_orient_matrix_UB_13      0.0369555000
_diffrn_orient_matrix_UB_21      0.0066822000
_diffrn_orient_matrix_UB_22      -0.2071438000
_diffrn_orient_matrix_UB_23      -0.0604332000
_diffrn_orient_matrix_UB_31      0.0211862000
_diffrn_orient_matrix_UB_32      -0.1076373000
_diffrn_orient_matrix_UB_33      0.1178927000
_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                1518
_reflns_number_total             1900
_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 1.171.43.96a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.94a 64-bit (release 20-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.160
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      1.075
_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)+(0.1672P)²+0.0569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2246
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Others
 Fixed Sof: H11A(0.5) H11B(0.5)
3.a Rotating group:
 N11(H11A,H11B)
3.b X=CH2 refined with riding coordinates:
 N12(H12A,H12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N6 N 0.7468(4) 0.0154(4) 0.30182(19) 0.0330(6) Uani 1 1 d . . . . .
N7 N 0.7365(4) 0.0837(4) 0.10723(19) 0.0331(6) Uani 1 1 d . . . . .
N8 N 0.5306(4) 0.1607(4) 0.18386(18) 0.0326(6) Uani 1 1 d . . . . .
N9 N 0.2122(4) 0.2882(4) 0.2916(2) 0.0339(6) Uani 1 1 d . . . . .
N10 N 0.3445(4) 0.1953(4) 0.37190(19) 0.0328(6) Uani 1 1 d . . . . .
N11 N 0.8500(4) -0.0258(4) 0.3999(2) 0.0391(6) Uani 1 1 d . . . . .
H11A H 0.809901 -0.123154 0.441519 0.047 Uiso 0.5 1 d R U P . .
H11B H 0.993132 -0.068525 0.374569 0.047 Uiso 0.5 1 d R U P . .
N12 N 1.0762(4) -0.0924(4) 0.1574(2) 0.0366(6) Uani 1 1 d . . . . .
H12A H 1.148628 -0.102248 0.083069 0.044 Uiso 1 1 calc R U . . .
H12B H 1.146232 -0.143940 0.214494 0.044 Uiso 1 1 calc R U . . .
N13 N 0.2462(4) 0.3416(4) 0.0825(2) 0.0377(6) Uani 1 1 d . . . . .
C2 C 0.8618(5) 0.0000(4) 0.1834(2) 0.0328(6) Uani 1 1 d . . . . .
C3 C 0.3228(4) 0.2692(4) 0.1774(2) 0.0326(6) Uani 1 1 d . . . . .
C4 C 0.5336(4) 0.1229(4) 0.2997(2) 0.0314(6) Uani 1 1 d . . . . .
H13A H 0.110(6) 0.410(6) 0.100(3) 0.034(8) Uiso 1 1 d . . . . .
H13B H 0.339(7) 0.308(6) 0.001(4) 0.062(12) Uiso 1 1 d . . . . .
H9 H 0.069(6) 0.351(6) 0.316(3) 0.040(9) Uiso 1 1 d . . . . .
N1 N -0.5561(4) 0.5677(4) 0.47181(19) 0.0327(5) Uani 1 1 d . . . . .
N2 N -0.2390(4) 0.4912(4) 0.3037(2) 0.0360(6) Uani 1 1 d . . . . .
N3 N -0.2209(4) 0.5432(4) 0.1904(2) 0.0366(6) Uani 1 1 d . . . . .
N4 N -0.4158(4) 0.6557(4) 0.1722(2) 0.0342(6) Uani 1 1 d . . . . .
N5 N -0.5644(4) 0.6802(4) 0.27439(19) 0.0345(6) Uani 1 1 d . . . . .
C1 C -0.4512(4) 0.5768(4) 0.3515(2) 0.0317(6) 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
N6 N11 1.404(3) . ?
N6 C2 1.401(3) . ?
N6 C4 1.368(3) . ?
N7 N8 1.403(3) . ?
N7 C2 1.320(4) . ?
N8 C3 1.351(4) . ?
N8 C4 1.349(3) . ?
N9 N10 1.400(3) . ?
N9 C3 1.348(3) . ?
N9 H9 0.89(4) . ?
N10 C4 1.299(3) . ?
N11 H11A 0.8803 . ?
N11 H11B 0.8811 . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N12 C2 1.324(4) . ?
N13 C3 1.313(4) . ?
N13 H13A 0.85(4) . ?
N13 H13B 0.99(4) . ?
N1 N1 1.247(5) 2_466 ?
N1 C1 1.421(3) . ?
N2 N3 1.332(3) . ?
N2 C1 1.334(3) . ?
N3 N4 1.327(4) . ?
N4 N5 1.340(3) . ?
N5 C1 1.321(4) . ?

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
C2 N6 N11 123.2(2) . . ?
C4 N6 N11 129.1(2) . . ?
C4 N6 C2 105.8(2) . . ?
C2 N7 N8 101.4(2) . . ?
C3 N8 N7 138.7(2) . . ?
C4 N8 N7 113.8(2) . . ?
C4 N8 C3 107.5(2) . . ?
N10 N9 H9 122(2) . . ?
C3 N9 N10 113.4(2) . . ?
C3 N9 H9 125(2) . . ?
C4 N10 N9 100.8(2) . . ?
N6 N11 H11A 110.2 . . ?
N6 N11 H11B 109.7 . . ?
H11A N11 H11B 109.4 . . ?
H12A N12 H12B 120.0 . . ?
C2 N12 H12A 120.0 . . ?
C2 N12 H12B 120.0 . . ?
C3 N13 H13A 112(2) . . ?
C3 N13 H13B 121(3) . . ?
H13A N13 H13B 126(3) . . ?
N7 C2 N6 113.7(2) . . ?
N7 C2 N12 126.4(2) . . ?
N12 C2 N6 119.9(2) . . ?
N9 C3 N8 103.8(2) . . ?
N13 C3 N8 128.2(2) . . ?
N13 C3 N9 127.9(3) . . ?
N8 C4 N6 105.4(2) . . ?
N10 C4 N6 140.2(2) . . ?
N10 C4 N8 114.5(2) . . ?
N1 N1 C1 113.9(3) 2_466 . ?
N3 N2 C1 104.2(2) . . ?
N4 N3 N2 109.4(2) . . ?
N3 N4 N5 109.3(2) . . ?
C1 N5 N4 104.2(2) . . ?
N2 C1 N1 126.6(3) . . ?
N5 C1 N1 120.5(2) . . ?
N5 C1 N2 112.9(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
N11 H11A N10 0.88 2.29 3.045(3) 143.7 2_656 yes
N12 H12A N7 0.88 2.17 3.039(3) 168.1 2_755 yes
N12 H12B N5 0.88 2.14 2.948(4) 151.6 1_745 yes
N13 H13A N3 0.85(4) 2.13(4) 2.955(3) 163(3) . yes
N13 H13B N4 0.99(4) 1.98(4) 2.906(3) 155(4) 2_565 yes
N9 H9 N2 0.89(4) 1.98(4) 2.829(4) 159(3) . 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
N7 N8 C3 N9 -178.7(3) . . . . ?
N7 N8 C3 N13 0.5(5) . . . . ?
N7 N8 C4 N6 -0.6(3) . . . . ?
N7 N8 C4 N10 179.3(2) . . . . ?
N8 N7 C2 N6 1.4(3) . . . . ?
N8 N7 C2 N12 -178.6(3) . . . . ?
N9 N10 C4 N6 179.5(3) . . . . ?
N9 N10 C4 N8 -0.3(3) . . . . ?
N10 N9 C3 N8 0.3(3) . . . . ?
N10 N9 C3 N13 -178.9(3) . . . . ?
N11 N6 C2 N7 -167.4(2) . . . . ?
N11 N6 C2 N12 12.7(4) . . . . ?
N11 N6 C4 N8 165.7(3) . . . . ?
N11 N6 C4 N10 -14.1(5) . . . . ?
C2 N6 C4 N8 1.4(3) . . . . ?
C2 N6 C4 N10 -178.4(3) . . . . ?
C2 N7 N8 C3 177.7(3) . . . . ?
C2 N7 N8 C4 -0.5(3) . . . . ?
C3 N8 C4 N6 -179.4(2) . . . . ?
C3 N8 C4 N10 0.5(3) . . . . ?
C3 N9 N10 C4 0.0(3) . . . . ?
C4 N6 C2 N7 -1.9(3) . . . . ?
C4 N6 C2 N12 178.2(2) . . . . ?
C4 N8 C3 N9 -0.5(3) . . . . ?
C4 N8 C3 N13 178.7(3) . . . . ?
N1 N1 C1 N2 -15.0(5) 2_466 . . . ?
N1 N1 C1 N5 166.0(3) 2_466 . . . ?
N2 N3 N4 N5 0.5(3) . . . . ?
N3 N2 C1 N1 -179.7(2) . . . . ?
N3 N2 C1 N5 -0.6(3) . . . . ?
N3 N4 N5 C1 -0.8(3) . . . . ?
N4 N5 C1 N1 180.0(2) . . . . ?
N4 N5 C1 N2 0.9(3) . . . . ?
C1 N2 N3 N4 0.1(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JS891
_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 4.122
_oxdiff_exptl_absorpt_empirical_full_min 0.269
_vrf_PLAT097_js1223an            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.16 eA-3  
RESPONSE: This crystal was slightly twinned or cracked and a better crystal 
was not able to be located in the sample.  This was the best data set of four
data sets collected.
;
####################################################################### 
# 
# 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_js223b
_database_code_depnum_ccdc_archive 'CCDC 2345097'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H N7 O10, 2(C3 H7 N8)'
_chemical_formula_sum            'C11 H15 N23 O10'
_chemical_formula_weight         629.46
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H15N23O10
_chemical_oxdiff_usercomment     'JS167F  Vial 2 Big'
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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.8497(4)
_cell_length_b                   6.69000(10)
_cell_length_c                   15.2054(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.346(4)
_cell_angle_gamma                90
_cell_volume                     1122.71(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9264
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      79.0490
_cell_measurement_theta_min      3.9860
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.620
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.472
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1722
0 -1 0 0.2023
2 -3 -7 0.1432
-1 -4 5 0.1848
0 0 9 0.0420
-5 0 -5 0.0467
5 0 5 0.0358
-5 -3 -1 0.1184
4 4 -4 0.1563
7 0 0 0.0209
-7 0 0 0.0248
7 0 -7 0.0260
-7 0 7 0.0303
0 0 -9 0.0438

_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.09
_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
-0.0006 0.9998 0.0008 0.0191 0.1343 0.1861
0.0006 -0.9998 -0.0008 -0.0191 -0.1343 -0.1861
2.4368 -3.1035 -6.8623 -0.2304 -0.9580 -0.1706
-1.1527 -3.7841 4.8313 -0.0287 -0.1136 -0.9931
0.1455 -0.0010 9.1232 -0.2375 0.7995 -0.5517
-4.6472 -0.1658 -5.1526 0.7585 -0.5816 0.2940
4.6260 0.1396 5.1840 -0.7568 0.5803 -0.3007
-5.4604 -2.5845 -0.9158 0.7232 -0.5558 -0.4099
3.6203 3.7124 -3.6910 -0.3390 0.2617 0.9036
7.2709 -0.0570 -0.3820 -0.9914 0.1306 -0.0089
-7.2709 0.0570 0.3820 0.9914 -0.1306 0.0089
7.0742 -0.0119 -6.9128 -0.8078 -0.4379 0.3946
-7.0643 -0.0145 6.9357 0.8054 0.4366 -0.4009
-0.1226 0.0272 -9.1342 0.2352 -0.7964 0.5572

_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  0.0350
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12928
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.339
_diffrn_reflns_theta_min         4.005
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  28.00   0.50    0.10    --  -46.85  19.00 -30.00  128
  2  ω    -69.00   5.00   0.50    0.10    --  -46.85  77.00   0.00  148
  3  ω    -65.00 -39.00   0.50    0.40    --  -91.75   0.00 -90.00   52
  4  ω    -67.00 -19.00   0.50    0.40    --  -91.75  61.00-180.00   96
  5  ω   -164.00-107.00   0.50    0.40    --  -91.75   0.00 -90.00  114
  6  ω   -118.00 -38.00   0.50    0.10    --  -46.85 -37.00-180.00  160
  7  ω   -120.00 -84.00   0.50    0.10    --  -46.85 -19.00  90.00   72
  8  ω    -81.00 -41.00   0.50    0.10    --  -46.85 -19.00  90.00   80
  9  ω    108.00 134.00   0.50    0.40    --  113.25  61.00-120.00   52
 10  ω    137.00 176.00   0.50    0.40    --  113.25  61.00-120.00   78
 11  ω    105.00 166.00   0.50    0.40    --  113.25  30.00-180.00  122
 12  ω    108.00 170.00   0.50    0.40    --  113.25  45.00-150.00  124
 13  ω    102.00 153.00   0.50    0.40    --  113.25  30.00 -60.00  102
 14  ω    106.00 161.00   0.50    0.40    --  113.25  61.00 -30.00  110
 15  ω    102.00 174.00   0.50    0.40    --  113.25  15.00  60.00  144
 16  ω    103.00 178.00   0.50    0.40    --  113.25  30.00 120.00  150
 17  ω    125.00 165.00   0.50    0.40    --  113.25  15.00 150.00   80
 18  ω    152.00 177.00   0.50    0.40    --  113.25  77.00  90.00   50
 19  ω    122.00 148.00   0.50    0.40    --  113.25 125.00 120.00   52
 20  ω     42.00  67.00   0.50    0.40    --  113.25 -61.00  90.00   50
 21  ω     46.00  94.00   0.50    0.40    --  113.25 -77.00  60.00   96
 22  ω     43.00  69.00   0.50    0.40    --  113.25 -61.00   0.00   52
 23  ω     52.00  77.00   0.50    0.40    --  113.25 -77.00 -60.00   50
 24  ω     42.00  67.00   0.50    0.40    --  113.25 -61.00 -90.00   50
 25  ω     42.00  73.00   0.50    0.40    --  113.25 -77.00-180.00   62
 26  ω      4.00  35.00   0.50    0.10    --   46.85 -19.00 -30.00   62
 27  ω     43.00  80.00   0.50    0.40    --  113.25 -94.00  60.00   74
 28  ω     78.00 108.00   0.50    0.40    --  113.25-125.00 120.00   60
 29  ω     47.00  74.00   0.50    0.40    --  113.25-125.00 120.00   54
 30  ω     43.00  91.00   0.50    0.10    --   46.85-125.00   0.00   96
 31  ω     44.00  74.00   0.50    0.40    --  113.25-125.00 -90.00   60
 32  ω     78.00 103.00   0.50    0.40    --  113.25-125.00 -90.00   50
 33  ω     80.00 105.00   0.50    0.40    --  113.25-107.00 -98.83   50
 34  ω     74.00 100.00   0.50    0.40    --  113.25 -94.00-180.00   52
 35  ω     47.00  72.00   0.50    0.40    --  113.25 -94.00-180.00   50
 36  ω     46.00  72.00   0.50    0.40    --  113.25-107.00 -98.83   52
 37  ω     45.00  94.00   0.50    0.40    --  113.25 -94.00 -90.00   98
 38  ω     75.00 104.00   0.50    0.40    --  113.25 -94.00   0.00   58
 39  ω     46.00  72.00   0.50    0.40    --  113.25 -94.00   0.00   52
 40  ω     70.00  96.00   0.50    0.40    --  113.25 -94.00 -30.00   52
 41  ω     73.00 102.00   0.50    0.40    --  113.25 -94.00  30.00   58
 42  ω     44.00  70.00   0.50    0.40    --  113.25 -94.00  30.00   52
 43  ω     78.00 103.00   0.50    0.40    --  113.25 -94.00 120.00   50
 44  ω     44.00  86.00   0.50    0.40    --  113.25 -94.00 150.00   84
 45  ω     49.00 104.00   0.50    0.40    --  113.25 -94.00 -60.00  110
 46  ω     48.00 100.00   0.50    0.40    --  113.25 -94.00-120.00  104
;
_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      -0.1374546000
_diffrn_orient_matrix_UB_12      0.0190264000
_diffrn_orient_matrix_UB_13      -0.0238436000
_diffrn_orient_matrix_UB_21      0.0236026000
_diffrn_orient_matrix_UB_22      0.1342551000
_diffrn_orient_matrix_UB_23      0.0872728000
_diffrn_orient_matrix_UB_31      -0.0029328000
_diffrn_orient_matrix_UB_32      0.1862166000
_diffrn_orient_matrix_UB_33      -0.0604046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.811
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                4252
_reflns_number_total             4293
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         4293
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0886
_refine_ls_restrained_S_all      1.172
_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)+8.0890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2023
_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.  Refinement stop aroun 8-9 % R1 value
for all three dtat sets collected on crystals grown in 
different ways.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4(8)
 0.6(8)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11: within 2A with sigma of 0.002 and sigma for terminal atoms
of 0.004 within 2A
N1 \\sim N2 \\sim N3 \\sim N4 \\sim N5 \\sim N6 \\sim N7 \\sim N8 \\sim N9
\\sim N10 \\sim N11 \\sim N12 \\sim N13 \\sim N14 \\sim N15 \\sim N16 \\sim N17
\\sim N18 \\sim N19 \\sim N20 \\sim N21 \\sim N22 \\sim N23: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.004 within 2A
O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim O7 \\sim O8 \\sim O9
\\sim O10: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
within 2A
4.a Rotating group:
 N14(H14A,H14B), N15(H15A,H15B), N23(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N8(H8), N16(H16)
4.c X=CH2 refined with riding coordinates:
 N13(H13A,H13B), N21(H21A,H21B), N22(H22A,H22B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5593(7) 0.4690(11) 0.3205(5) 0.0266(15) Uani 1 1 d . . . . .
O2 O 0.6494(7) 0.6819(11) 0.2571(5) 0.0270(16) Uani 1 1 d . . . . .
O3 O 0.9644(7) 0.4742(11) 0.4469(5) 0.0286(16) Uani 1 1 d . . . . .
O4 O 0.8821(7) 0.6289(10) 0.3123(5) 0.0259(14) Uani 1 1 d . . . . .
O5 O 0.8771(7) -0.1162(9) 0.4958(5) 0.0272(15) Uani 1 1 d . . . . .
O6 O 0.8229(7) 0.0683(10) 0.3704(4) 0.0259(15) Uani 1 1 d . . . . .
O7 O 0.5832(6) -0.0629(12) 0.5677(6) 0.0332(18) Uani 1 1 d . . . . .
O8 O 0.6769(8) -0.2616(11) 0.6846(5) 0.0341(18) Uani 1 1 d . . . . .
O9 O 0.9858(7) 0.0250(12) 0.6960(6) 0.0315(17) Uani 1 1 d . . . . .
O10 O 0.9134(8) -0.2342(12) 0.7439(5) 0.0361(19) Uani 1 1 d . . . . .
N1 N 0.7295(7) 0.3412(11) 0.5992(5) 0.0202(13) Uani 1 1 d . U . . .
H1 H 0.709287 0.365034 0.648411 0.024 Uiso 1 1 calc R U . . .
N2 N 0.7214(8) 0.4812(11) 0.5333(5) 0.0201(13) Uani 1 1 d . U . . .
N3 N 0.8320(8) 0.0382(11) 0.4538(5) 0.0207(16) Uani 1 1 d . . . . .
N4 N 0.6560(8) 0.5552(13) 0.3183(6) 0.0245(18) Uani 1 1 d . . . . .
N5 N 0.8749(8) 0.5409(11) 0.3805(5) 0.0198(16) Uani 1 1 d . . . . .
N6 N 0.6784(8) -0.1208(11) 0.6336(6) 0.0235(16) Uani 1 1 d . . . . .
N7 N 0.8955(8) -0.0721(11) 0.6958(6) 0.0203(16) Uani 1 1 d . . . . .
C1 C 0.7603(9) 0.4970(13) 0.3869(6) 0.0194(14) Uani 1 1 d . U . . .
C2 C 0.7598(8) 0.3852(12) 0.4713(6) 0.0176(12) Uani 1 1 d . U . . .
C3 C 0.7919(8) 0.1894(12) 0.5010(6) 0.0156(12) Uani 1 1 d . U . . .
C4 C 0.7718(8) 0.1579(12) 0.5835(6) 0.0174(12) Uani 1 1 d . U . . .
C5 C 0.7828(8) -0.0077(13) 0.6429(6) 0.0190(14) Uani 1 1 d . U . . .
N8 N 0.4182(9) 0.7744(15) 0.3496(6) 0.0307(17) Uani 1 1 d . U . . .
H8 H 0.459878 0.671115 0.342274 0.037 Uiso 1 1 calc R U . . .
N9 N 0.3140(9) 0.7534(15) 0.3725(7) 0.0319(17) Uani 1 1 d . U . . .
N10 N 0.3616(9) 1.0711(14) 0.3556(6) 0.0279(16) Uani 1 1 d . U . . .
N11 N 0.3334(9) 1.2734(15) 0.3602(6) 0.0283(16) Uani 1 1 d . U . . .
N12 N 0.2013(8) 1.0590(14) 0.3902(6) 0.0272(17) Uani 1 1 d . U . . .
N13 N 0.5406(8) 1.0284(15) 0.3196(6) 0.029(2) Uani 1 1 d . . . . .
H13A H 0.593047 0.946222 0.310155 0.035 Uiso 1 1 calc R U . . .
H13B H 0.549129 1.158370 0.315575 0.035 Uiso 1 1 calc R U . . .
N14 N 0.1730(9) 1.4093(16) 0.3970(7) 0.031(2) Uani 1 1 d . . . . .
H14A H 0.110226 1.370318 0.411716 0.038 Uiso 1 1 d R U . . .
H14B H 0.221759 1.482659 0.444438 0.038 Uiso 1 1 d R U . . .
N15 N 0.1081(8) 0.9944(12) 0.4196(6) 0.0212(15) Uani 1 1 d . U . . .
H15A H 0.136421 0.968272 0.481153 0.025 Uiso 1 1 d R U . . .
H15B H 0.053391 1.091549 0.408352 0.025 Uiso 1 1 d R U . . .
C6 C 0.4481(10) 0.9559(17) 0.3402(7) 0.025(2) Uani 1 1 d . . . . .
C7 C 0.2865(10) 0.9411(16) 0.3750(7) 0.026(2) Uani 1 1 d . . . . .
C8 C 0.2337(11) 1.251(2) 0.3820(7) 0.032(2) Uani 1 1 d . . . . .
N16 N 0.1321(8) 0.7230(12) 0.6476(6) 0.0222(14) Uani 1 1 d . U . . .
H16 H 0.089147 0.825130 0.654324 0.027 Uiso 1 1 calc R U . . .
N17 N 0.2376(8) 0.7416(13) 0.6263(6) 0.0248(14) Uani 1 1 d . U . . .
N18 N 0.1887(8) 0.4239(12) 0.6388(6) 0.0218(14) Uani 1 1 d . U . . .
N19 N 0.2201(8) 0.2239(12) 0.6341(6) 0.0222(14) Uani 1 1 d . U . . .
N20 N 0.3524(8) 0.4410(13) 0.6070(6) 0.0240(16) Uani 1 1 d . U . . .
N21 N 0.0142(9) 0.4555(13) 0.6762(7) 0.029(2) Uani 1 1 d . . . . .
H21A H 0.005644 0.325232 0.678711 0.034 Uiso 1 1 calc R U . . .
H21B H -0.037997 0.536219 0.687011 0.034 Uiso 1 1 calc R U . . .
N22 N 0.3824(9) 0.0927(13) 0.5990(6) 0.0259(18) Uani 1 1 d . . . . .
H22A H 0.360760 -0.031507 0.603493 0.031 Uiso 1 1 calc R U . . .
H22B H 0.446990 0.117417 0.585089 0.031 Uiso 1 1 calc R U . . .
N23 N 0.4467(8) 0.4927(13) 0.5779(6) 0.0255(16) Uani 1 1 d . U . . .
H23A H 0.423000 0.573312 0.527891 0.031 Uiso 1 1 d R U . . .
H23B H 0.501410 0.559440 0.624391 0.031 Uiso 1 1 d R U . . .
C9 C 0.1043(10) 0.5292(15) 0.6564(7) 0.026(2) Uani 1 1 d . . . . .
C10 C 0.2658(10) 0.5561(14) 0.6217(7) 0.024(2) Uani 1 1 d . . . . .
C11 C 0.3182(10) 0.2420(15) 0.6130(7) 0.0233(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.294(12) . ?
O2 N4 1.240(11) . ?
O3 N5 1.250(11) . ?
O4 N5 1.222(10) . ?
O5 N3 1.229(10) . ?
O6 N3 1.248(10) . ?
O7 N6 1.266(11) . ?
O8 N6 1.224(11) . ?
O9 N7 1.250(12) . ?
O10 N7 1.282(11) . ?
N1 H1 0.8800 . ?
N1 N2 1.349(11) . ?
N1 C4 1.378(11) . ?
N2 C2 1.350(11) . ?
N3 C3 1.419(11) . ?
N4 C1 1.352(13) . ?
N5 C1 1.427(12) . ?
N6 C5 1.413(12) . ?
N7 C5 1.355(12) . ?
C1 C2 1.487(12) . ?
C2 C3 1.393(12) . ?
C3 C4 1.376(12) . ?
C4 C5 1.405(12) . ?
N8 H8 0.8800 . ?
N8 N9 1.406(13) . ?
N8 C6 1.288(15) . ?
N9 C7 1.301(15) . ?
N10 N11 1.402(14) . ?
N10 C6 1.370(14) . ?
N10 C7 1.350(14) . ?
N11 C8 1.346(14) . ?
N12 N15 1.402(11) . ?
N12 C7 1.366(14) . ?
N12 C8 1.361(16) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
N13 C6 1.335(13) . ?
N14 H14A 0.8895 . ?
N14 H14B 0.8895 . ?
N14 C8 1.344(16) . ?
N15 H15A 0.8898 . ?
N15 H15B 0.8895 . ?
N16 H16 0.8800 . ?
N16 N17 1.406(12) . ?
N16 C9 1.356(13) . ?
N17 C10 1.294(13) . ?
N18 N19 1.398(11) . ?
N18 C9 1.328(14) . ?
N18 C10 1.363(13) . ?
N19 C11 1.318(13) . ?
N20 N23 1.387(12) . ?
N20 C10 1.365(14) . ?
N20 C11 1.404(13) . ?
N21 H21A 0.8800 . ?
N21 H21B 0.8800 . ?
N21 C9 1.307(14) . ?
N22 H22A 0.8800 . ?
N22 H22B 0.8800 . ?
N22 C11 1.320(14) . ?
N23 H23A 0.8898 . ?
N23 H23B 0.8865 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 122.5 . . ?
N2 N1 C4 115.0(7) . . ?
C4 N1 H1 122.5 . . ?
N1 N2 C2 103.7(7) . . ?
O5 N3 O6 121.6(8) . . ?
O5 N3 C3 119.9(7) . . ?
O6 N3 C3 118.5(7) . . ?
O1 N4 C1 114.9(8) . . ?
O2 N4 O1 120.6(8) . . ?
O2 N4 C1 124.5(9) . . ?
O3 N5 C1 114.8(7) . . ?
O4 N5 O3 123.8(8) . . ?
O4 N5 C1 121.3(8) . . ?
O7 N6 C5 114.2(8) . . ?
O8 N6 O7 121.5(9) . . ?
O8 N6 C5 124.2(9) . . ?
O9 N7 O10 118.3(9) . . ?
O9 N7 C5 119.6(8) . . ?
O10 N7 C5 122.0(9) . . ?
N4 C1 N5 120.9(8) . . ?
N4 C1 C2 121.3(8) . . ?
N5 C1 C2 117.8(8) . . ?
N2 C2 C1 118.2(7) . . ?
N2 C2 C3 110.0(8) . . ?
C3 C2 C1 131.8(8) . . ?
C2 C3 N3 127.5(8) . . ?
C4 C3 N3 123.6(7) . . ?
C4 C3 C2 108.8(7) . . ?
N1 C4 C5 123.0(8) . . ?
C3 C4 N1 102.5(7) . . ?
C3 C4 C5 134.5(8) . . ?
N7 C5 N6 121.8(8) . . ?
N7 C5 C4 118.2(8) . . ?
C4 C5 N6 119.0(8) . . ?
N9 N8 H8 122.4 . . ?
C6 N8 H8 122.4 . . ?
C6 N8 N9 115.1(10) . . ?
C7 N9 N8 99.3(9) . . ?
C6 N10 N11 139.3(9) . . ?
C7 N10 N11 115.0(9) . . ?
C7 N10 C6 105.6(9) . . ?
C8 N11 N10 98.8(9) . . ?
C7 N12 N15 126.3(9) . . ?
C8 N12 N15 127.0(9) . . ?
C8 N12 C7 106.2(9) . . ?
H13A N13 H13B 120.0 . . ?
C6 N13 H13A 120.0 . . ?
C6 N13 H13B 120.0 . . ?
H14A N14 H14B 108.3 . . ?
C8 N14 H14A 111.1 . . ?
C8 N14 H14B 110.0 . . ?
N12 N15 H15A 110.9 . . ?
N12 N15 H15B 108.5 . . ?
H15A N15 H15B 108.3 . . ?
N8 C6 N10 104.9(9) . . ?
N8 C6 N13 130.6(11) . . ?
N13 C6 N10 124.4(10) . . ?
N9 C7 N10 115.0(10) . . ?
N9 C7 N12 140.4(10) . . ?
N10 C7 N12 104.5(9) . . ?
N11 C8 N12 115.4(10) . . ?
N14 C8 N11 121.8(12) . . ?
N14 C8 N12 122.8(11) . . ?
N17 N16 H16 124.0 . . ?
C9 N16 H16 124.0 . . ?
C9 N16 N17 112.1(8) . . ?
C10 N17 N16 101.3(9) . . ?
C9 N18 N19 138.8(9) . . ?
C9 N18 C10 107.5(8) . . ?
C10 N18 N19 113.7(8) . . ?
C11 N19 N18 101.5(8) . . ?
N23 N20 C11 122.9(8) . . ?
C10 N20 N23 130.8(9) . . ?
C10 N20 C11 105.7(8) . . ?
H21A N21 H21B 120.0 . . ?
C9 N21 H21A 120.0 . . ?
C9 N21 H21B 120.0 . . ?
H22A N22 H22B 120.0 . . ?
C11 N22 H22A 120.0 . . ?
C11 N22 H22B 120.0 . . ?
N20 N23 H23A 112.5 . . ?
N20 N23 H23B 108.1 . . ?
H23A N23 H23B 106.8 . . ?
N18 C9 N16 105.0(9) . . ?
N21 C9 N16 129.2(10) . . ?
N21 C9 N18 125.8(9) . . ?
N17 C10 N18 114.1(10) . . ?
N17 C10 N20 140.7(10) . . ?
N18 C10 N20 105.2(8) . . ?
N19 C11 N20 113.9(9) . . ?
N19 C11 N22 125.5(10) . . ?
N22 C11 N20 120.6(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.88 2.05 2.890(10) 160.3 2_565 yes
N1 H1 O4 0.88 2.59 3.090(10) 117.2 2_565 yes
N8 H8 O1 0.88 1.90 2.776(13) 173.4 . yes
N13 H13A O2 0.88 2.15 2.972(12) 155.5 . yes
N13 H13B O1 0.88 2.08 2.956(12) 172.1 1_565 yes
N14 H14A O3 0.89 2.10 2.870(12) 143.7 1_465 yes
N16 H16 O9 0.88 2.06 2.926(12) 166.5 1_465 yes
N21 H21A O9 0.88 2.05 2.928(12) 175.1 1_455 yes
N21 H21B O10 0.88 1.95 2.772(11) 155.1 1_465 yes
N22 H22A N17 0.88 2.22 3.026(13) 152.4 1_545 yes
N22 H22B O7 0.88 2.11 2.791(12) 134.0 . yes
N23 H23B O8 0.89 2.28 3.091(12) 151.5 1_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N4 C1 N5 164.7(8) . . . . ?
O1 N4 C1 C2 -15.2(13) . . . . ?
O2 N4 C1 N5 -15.7(14) . . . . ?
O2 N4 C1 C2 164.4(8) . . . . ?
O3 N5 C1 N4 -178.0(8) . . . . ?
O3 N5 C1 C2 1.9(11) . . . . ?
O4 N5 C1 N4 -1.3(13) . . . . ?
O4 N5 C1 C2 178.6(8) . . . . ?
O5 N3 C3 C2 167.3(9) . . . . ?
O5 N3 C3 C4 -16.8(14) . . . . ?
O6 N3 C3 C2 -11.0(14) . . . . ?
O6 N3 C3 C4 164.9(9) . . . . ?
O7 N6 C5 N7 -166.2(8) . . . . ?
O7 N6 C5 C4 2.7(12) . . . . ?
O8 N6 C5 N7 14.7(14) . . . . ?
O8 N6 C5 C4 -176.4(8) . . . . ?
O9 N7 C5 N6 174.4(8) . . . . ?
O9 N7 C5 C4 5.4(13) . . . . ?
O10 N7 C5 N6 -3.4(13) . . . . ?
O10 N7 C5 C4 -172.4(8) . . . . ?
N1 N2 C2 C1 178.9(8) . . . . ?
N1 N2 C2 C3 -0.7(10) . . . . ?
N1 C4 C5 N6 79.7(12) . . . . ?
N1 C4 C5 N7 -111.0(10) . . . . ?
N2 N1 C4 C3 0.3(11) . . . . ?
N2 N1 C4 C5 -178.0(8) . . . . ?
N2 C2 C3 N3 177.4(10) . . . . ?
N2 C2 C3 C4 0.9(11) . . . . ?
N3 C3 C4 N1 -177.3(8) . . . . ?
N3 C3 C4 C5 0.7(17) . . . . ?
N4 C1 C2 N2 -67.4(12) . . . . ?
N4 C1 C2 C3 112.1(11) . . . . ?
N5 C1 C2 N2 112.7(10) . . . . ?
N5 C1 C2 C3 -67.8(13) . . . . ?
C1 C2 C3 N3 -2.1(16) . . . . ?
C1 C2 C3 C4 -178.6(10) . . . . ?
C2 C3 C4 N1 -0.7(10) . . . . ?
C2 C3 C4 C5 177.3(10) . . . . ?
C3 C4 C5 N6 -98.0(13) . . . . ?
C3 C4 C5 N7 71.3(14) . . . . ?
C4 N1 N2 C2 0.2(11) . . . . ?
N8 N9 C7 N10 0.5(12) . . . . ?
N8 N9 C7 N12 179.1(14) . . . . ?
N9 N8 C6 N10 -0.7(12) . . . . ?
N9 N8 C6 N13 179.5(11) . . . . ?
N10 N11 C8 N12 -0.2(11) . . . . ?
N10 N11 C8 N14 178.0(10) . . . . ?
N11 N10 C6 N8 178.0(12) . . . . ?
N11 N10 C6 N13 -2.3(19) . . . . ?
N11 N10 C7 N9 -178.8(10) . . . . ?
N11 N10 C7 N12 2.1(12) . . . . ?
N15 N12 C7 N9 6(2) . . . . ?
N15 N12 C7 N10 -175.0(9) . . . . ?
N15 N12 C8 N11 174.4(9) . . . . ?
N15 N12 C8 N14 -3.8(16) . . . . ?
C6 N8 N9 C7 0.2(12) . . . . ?
C6 N10 N11 C8 -178.1(12) . . . . ?
C6 N10 C7 N9 -0.9(13) . . . . ?
C6 N10 C7 N12 180.0(8) . . . . ?
C7 N10 N11 C8 -1.2(11) . . . . ?
C7 N10 C6 N8 0.9(11) . . . . ?
C7 N10 C6 N13 -179.3(10) . . . . ?
C7 N12 C8 N11 1.5(12) . . . . ?
C7 N12 C8 N14 -176.7(10) . . . . ?
C8 N12 C7 N9 179.3(15) . . . . ?
C8 N12 C7 N10 -2.0(11) . . . . ?
N16 N17 C10 N18 -0.5(11) . . . . ?
N16 N17 C10 N20 -178.3(13) . . . . ?
N17 N16 C9 N18 -1.5(11) . . . . ?
N17 N16 C9 N21 179.5(10) . . . . ?
N18 N19 C11 N20 1.9(11) . . . . ?
N18 N19 C11 N22 -178.8(10) . . . . ?
N19 N18 C9 N16 -179.8(11) . . . . ?
N19 N18 C9 N21 -0.8(19) . . . . ?
N19 N18 C10 N17 -179.7(9) . . . . ?
N19 N18 C10 N20 -1.2(11) . . . . ?
N23 N20 C10 N17 -9(2) . . . . ?
N23 N20 C10 N18 172.9(9) . . . . ?
N23 N20 C11 N19 -174.4(8) . . . . ?
N23 N20 C11 N22 6.2(14) . . . . ?
C9 N16 N17 C10 1.3(10) . . . . ?
C9 N18 N19 C11 -179.4(12) . . . . ?
C9 N18 C10 N17 -0.4(12) . . . . ?
C9 N18 C10 N20 178.1(8) . . . . ?
C10 N18 N19 C11 -0.4(11) . . . . ?
C10 N18 C9 N16 1.1(11) . . . . ?
C10 N18 C9 N21 -179.9(10) . . . . ?
C10 N20 C11 N19 -2.7(12) . . . . ?
C10 N20 C11 N22 177.9(9) . . . . ?
C11 N20 C10 N17 -179.9(13) . . . . ?
C11 N20 C10 N18 2.2(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 'JS167F  Vial 2 Big'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.589
_oxdiff_exptl_absorpt_empirical_full_min 0.745
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4(8)
2 0.6(8)

_vrf_PLAT340_js223b              
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.012 Ang.
RESPONSE: This is due the crystallographic psedo center created by the inversion twin
which attempts to model the very severe disorder in the higher space group failed in our hands.
;
_vrf_PLAT430_js1222b             
;
PROBLEM: Short Inter D...A Contact O3 ..N4 . 2.81 Ang.
RESPONSE: This distance is due to the packing arrangement of the molecules.
;
_vrf_PLAT430_js223b              
;
PROBLEM: Short Inter D...A Contact O6 ..O10 . 2.75 Ang.
RESPONSE:  This is due to the Packing of the molecules and the hydrogen bonding network 
that most likely dominates the packing energy.
;
####################################################################### 
# 
# 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_js1123k
_database_code_depnum_ccdc_archive 'CCDC 2345096'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-11-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N8 O4, 2(C3 H7 N8)'
_chemical_formula_sum            'C8 H14 N24 O4'
_chemical_formula_weight         510.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H14N24O4
_chemical_oxdiff_usercomment     JS856-CY-DMSO
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                   19.8933(7)
_cell_length_b                   4.99426(12)
_cell_length_c                   20.8330(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.073(4)
_cell_angle_gamma                90
_cell_volume                     1874.77(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7538
_cell_measurement_temperature    99.98(12)
_cell_measurement_theta_max      76.0660
_cell_measurement_theta_min      4.0350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.301
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.94a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.808
_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 0.0952
0 1 0 0.0904
-1 0 -1 0.0186
1 0 1 0.0048
13 0 -4 0.0311
-13 0 5 0.0034

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.024
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0063 -0.9998 -0.0039 0.2133 0.2228 -0.0040
0.0133 1.0001 -0.0022 -0.2143 -0.2220 0.0049
-1.0018 0.0001 -0.9992 0.0039 -0.0063 -0.1409
1.0019 -0.0010 0.9998 -0.0037 0.0065 0.1410
12.7307 -0.2424 -3.6594 -0.4964 0.5913 0.6381
-12.8546 0.2668 5.0465 0.5377 -0.6397 -0.5491

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17543
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.775
_diffrn_reflns_theta_min         2.575
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  20.00   0.50    0.08    --  -47.36  19.00  30.00   92
  2  ω    -25.00   1.00   0.50    0.08    --  -47.36  19.00 -60.00   52
  3  ω    -22.00  27.00   0.50    0.08    --  -47.36  19.00 -90.00   98
  4  ω    -16.00  20.00   0.50    0.08    --  -47.36  19.00-150.00   72
  5  ω    -25.00   4.00   0.50    0.08    --  -47.36  19.00-180.00   58
  6  ω    -22.00  25.00   0.50    0.08    --   47.36 -19.00-150.00   94
  7  ω    115.00 176.00   0.50    0.31    --  107.75  77.00-180.00  122
  8  ω    114.00 156.00   0.50    0.31    --  107.75 136.00-101.00   84
  9  ω    126.00 151.00   0.50    0.31    --  107.75  77.00 -30.00   50
 10  ω    140.00 175.00   0.50    0.31    --  107.75  45.00-120.00   70
 11  ω     96.00 122.00   0.50    0.31    --  107.75  45.00-120.00   52
 12  ω     99.00 175.00   0.50    0.31    --  107.75  30.00 -30.00  152
 13  ω    101.00 169.00   0.50    0.31    --  107.75  15.00 -30.00  136
 14  ω    104.00 176.00   0.50    0.31    --  107.75  45.00  30.00  144
 15  ω    111.00 136.00   0.50    0.31    --  107.75 133.00  80.00   50
 16  ω    110.00 177.00   0.50    0.31    --  107.75  77.00 150.00  134
 17  ω    112.00 178.00   0.50    0.31    --  107.75  15.00  90.00  132
 18  ω     61.00  93.00   0.50    0.31    --  107.75 -77.00 -30.00   64
 19  ω     39.00  68.00   0.50    0.31    --  107.75 -61.00-120.00   58
 20  ω     35.00  73.00   0.50    0.31    --  107.75 -77.00   0.00   76
 21  ω     37.00  65.00   0.50    0.31    --  107.75 -61.00  30.00   56
 22  ω     38.00  71.00   0.50    0.31    --  107.75 -61.00  90.00   66
 23  ω     43.00  69.00   0.50    0.31    --  107.75 -61.00 150.00   52
 24  ω     37.00  70.00   0.50    0.31    --  107.75 -61.00  60.00   66
 25  ω     43.00  71.00   0.50    0.31    --  107.75 -61.00-150.00   56
 26  ω     35.00  71.00   0.50    0.31    --  107.75 -61.00-180.00   72
 27  ω     48.00  73.00   0.50    0.08    --   47.36-136.00-166.00   50
 28  ω     56.00  81.00   0.50    0.31    --  107.75-136.00-166.00   50
 29  ω     40.00 107.00   0.50    0.31    --  107.75-125.00 -30.00  134
 30  ω     53.00  78.00   0.50    0.31    --  107.75-133.00  12.00   50
 31  ω     57.00 104.00   0.50    0.31    --  107.75 -94.00  90.00   94
 32  ω     53.00  88.00   0.50    0.31    --  107.75-125.00 150.00   70
 33  ω     63.00  97.00   0.50    0.08    --   47.36-133.00  12.00   68
 34  ω     79.00 104.00   0.50    0.31    --  107.75 -94.00   0.00   50
 35  ω     41.00  77.00   0.50    0.31    --  107.75 -94.00 -30.00   72
 36  ω     60.00 100.00   0.50    0.31    --  107.75 -94.00  60.00   80
 37  ω     52.00 104.00   0.50    0.31    --  107.75 -94.00-120.00  104
 38  ω     35.00 100.00   0.50    0.31    --  107.75 -94.00-180.00  130
 39  ω     44.00  70.00   0.50    0.31    --  107.75 -94.00-150.00   52
 40  ω     75.00 103.00   0.50    0.31    --  107.75 -94.00-150.00   56
 41  ω     61.00 104.00   0.50    0.31    --  107.75 -94.00 -60.00   86
 42  ω     74.00 104.00   0.50    0.31    --  107.75 -94.00 120.00   60
 43  ω     65.00  98.00   0.50    0.31    --  107.75 -94.00 150.00   66
 44  ω     94.00 119.00   0.50    0.31    --  107.75 -85.00  66.39   50
 45  ω     70.00  98.00   0.50    0.31    --  107.75 -94.00  30.00   56
 46  ω    109.00 134.00   0.50    0.31    --  107.75 -86.00 -92.62   50
 47  ω     95.00 122.00   0.50    0.31    --  107.75 -86.00-126.63   54
 48  ω     49.00  74.00   0.50    0.31    --  107.75 -86.00 -92.62   50
 49  ω   -117.00 -48.00   0.50    0.08    --  -47.36 -37.00-120.00  138
 50  ω   -118.00 -69.00   0.50    0.08    --  -47.36-136.00-166.00   98
 51  ω   -136.00-111.00   0.50    0.31    --  -86.25-136.00-166.00   50
 52  ω   -117.00 -71.00   0.50    0.08    --  -47.36-133.00  12.00   92
 53  ω   -114.00 -89.00   0.50    0.31    --  -86.25-133.00  12.00   50
 54  ω    -50.00 -14.00   0.50    0.31    --  -86.25  45.00  90.00   72
 55  ω    -85.00 -49.00   0.50    0.08    --  -47.36 133.00  80.00   72
 56  ω    -80.00 -55.00   0.50    0.08    --  -47.36 136.00-101.00   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      -0.0343042000
_diffrn_orient_matrix_UB_12      -0.2137185000
_diffrn_orient_matrix_UB_13      0.0304655000
_diffrn_orient_matrix_UB_21      0.0341620000
_diffrn_orient_matrix_UB_22      -0.2224837000
_diffrn_orient_matrix_UB_23      -0.0279908000
_diffrn_orient_matrix_UB_31      0.0704403000
_diffrn_orient_matrix_UB_32      0.0041338000
_diffrn_orient_matrix_UB_33      0.0703987000
_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_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2958
_reflns_number_total             3816
_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 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.029
_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)+(0.0503P)²+0.9905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          ?
_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 0.39742(9) 1.1582(4) 0.17556(9) 0.0317(4) Uani 1 1 d . . . . .
O2 O 0.41608(9) 1.3960(4) 0.26913(9) 0.0297(4) Uani 1 1 d . . . . .
O3 O 0.80529(8) 2.0944(3) 0.50001(8) 0.0259(4) Uani 1 1 d . . . . .
O4 O 0.69235(9) 2.0255(4) 0.48761(9) 0.0288(4) Uani 1 1 d . . . . .
N1 N 0.55131(10) 1.5707(4) 0.34013(10) 0.0230(4) Uani 1 1 d . . . . .
N2 N 0.60979(10) 1.7099(4) 0.38618(10) 0.0227(4) Uani 1 1 d . . . . .
N3 N 0.69010(10) 1.3950(4) 0.36782(10) 0.0227(4) Uani 1 1 d . . . . .
N4 N 0.63390(10) 1.2598(4) 0.32430(10) 0.0225(4) Uani 1 1 d . . . . .
N5 N 0.51200(10) 1.2195(4) 0.25202(10) 0.0232(4) Uani 1 1 d . . . . .
N6 N 0.44056(10) 1.2653(4) 0.23309(10) 0.0237(4) Uani 1 1 d . . . . .
N7 N 0.74352(10) 1.7627(4) 0.43127(10) 0.0230(4) Uani 1 1 d . . . . .
N24 N 0.74573(10) 1.9638(4) 0.47259(10) 0.0225(4) Uani 1 1 d . . . . .
C1 C 0.56407(12) 1.3618(4) 0.30740(11) 0.0213(4) Uani 1 1 d . . . . .
C2 C 0.67699(12) 1.6300(4) 0.39554(11) 0.0211(4) Uani 1 1 d . . . . .
N16 N 0.52465(10) 0.2667(4) 0.06552(9) 0.0202(4) Uani 1 1 d . . . . .
N17 N 0.53352(10) 0.4695(4) 0.11503(9) 0.0187(4) Uani 1 1 d . . . . .
N18 N 0.54232(10) 0.7921(4) 0.18474(10) 0.0205(4) Uani 1 1 d . . . . .
H18 H 0.5306(16) 0.932(7) 0.2039(16) 0.030(7) Uiso 1 1 d . . . . .
N19 N 0.61369(9) 0.6791(4) 0.21234(9) 0.0195(4) Uani 1 1 d . . . . .
N20 N 0.64144(10) 0.2840(4) 0.15361(9) 0.0193(4) Uani 1 1 d . . . . .
N21 N 0.71488(10) 0.2202(4) 0.19939(10) 0.0222(4) Uani 1 1 d . . . . .
H21A H 0.7167(16) 0.054(7) 0.2168(16) 0.028(7) Uiso 1 1 d . . . . .
H21B H 0.740(2) 0.238(8) 0.173(2) 0.053(10) Uiso 1 1 d . . . . .
N22 N 0.61161(11) -0.0595(4) 0.06631(10) 0.0212(4) Uani 1 1 d . . . . .
H22A H 0.6609(17) -0.077(6) 0.0768(15) 0.023(6) Uiso 1 1 d . . . . .
H22B H 0.5777(16) -0.113(6) 0.0276(16) 0.019(6) Uiso 1 1 d . . . . .
N23 N 0.42399(11) 0.7392(4) 0.08694(11) 0.0257(4) Uani 1 1 d . . . . .
H23A H 0.4076(19) 0.867(8) 0.1074(19) 0.043(9) Uiso 1 1 d . . . . .
H23B H 0.394(2) 0.633(8) 0.0579(19) 0.040(9) Uiso 1 1 d . . . . .
C6 C 0.59201(12) 0.1589(4) 0.09204(11) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.60326(11) 0.4848(4) 0.16711(11) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.49428(12) 0.6693(4) 0.12634(11) 0.0199(4) Uani 1 1 d . . . . .
N8 N 0.10920(11) 0.9062(4) 0.05966(10) 0.0249(4) Uani 1 1 d . . . . .
N9 N 0.09146(10) 0.6954(4) 0.09436(10) 0.0234(4) Uani 1 1 d . . . . .
N10 N 0.05685(11) 0.3765(4) 0.14139(10) 0.0250(4) Uani 1 1 d . . . . .
H10 H 0.0289(18) 0.255(7) 0.1509(17) 0.036(8) Uiso 1 1 d . . . . .
N11 N 0.13503(11) 0.3703(4) 0.17508(11) 0.0269(4) Uani 1 1 d . . . . .
N12 N 0.21120(10) 0.6982(4) 0.14338(10) 0.0246(4) Uani 1 1 d . . . . .
N13 N 0.28590(11) 0.6363(4) 0.17582(12) 0.0284(4) Uani 1 1 d . . . . .
H13A H 0.3034(16) 0.681(6) 0.2191(17) 0.024(7) Uiso 1 1 d . . . . .
H13B H 0.294(2) 0.448(8) 0.167(2) 0.054(10) Uiso 1 1 d . . . . .
N14 N 0.23178(13) 1.0515(5) 0.08093(13) 0.0310(5) Uani 1 1 d . . . . .
H14A H 0.2155(17) 1.170(7) 0.0487(17) 0.031(7) Uiso 1 1 d . . . . .
H14B H 0.277(2) 1.028(7) 0.1056(18) 0.036(8) Uiso 1 1 d . . . . .
N15 N -0.03995(11) 0.6302(4) 0.05138(11) 0.0259(4) Uani 1 1 d . . . . .
H15A H -0.0783(17) 0.521(6) 0.0525(16) 0.031(7) Uiso 1 1 d . . . . .
H15B H -0.0464(17) 0.770(7) 0.0248(17) 0.033(8) Uiso 1 1 d . . . . .
C3 C 0.18369(13) 0.8958(5) 0.09190(12) 0.0256(5) Uani 1 1 d . . . . .
C4 C 0.03038(12) 0.5726(5) 0.09269(11) 0.0229(4) Uani 1 1 d . . . . .
C5 C 0.15107(12) 0.5700(5) 0.14345(11) 0.0218(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N6 1.260(3) . ?
O2 N6 1.240(3) . ?
O3 N24 1.258(3) . ?
O4 N24 1.266(2) . ?
N1 N2 1.346(3) . ?
N1 C1 1.328(3) . ?
N2 C2 1.328(3) . ?
N3 N4 1.292(3) . ?
N3 C2 1.381(3) . ?
N4 C1 1.378(3) . ?
N5 N6 1.324(3) . ?
N5 C1 1.377(3) . ?
N7 N24 1.311(3) . ?
N7 C2 1.382(3) . ?
N16 N17 1.402(2) . ?
N16 C6 1.328(3) . ?
N17 C7 1.354(3) . ?
N17 C8 1.348(3) . ?
N18 H18 0.89(3) . ?
N18 N19 1.405(3) . ?
N18 C8 1.336(3) . ?
N19 C7 1.307(3) . ?
N20 N21 1.402(3) . ?
N20 C6 1.390(3) . ?
N20 C7 1.358(3) . ?
N21 H21A 0.90(3) . ?
N21 H21B 0.90(4) . ?
N22 H22A 0.91(3) . ?
N22 H22B 0.85(3) . ?
N22 C6 1.344(3) . ?
N23 H23A 0.90(4) . ?
N23 H23B 0.83(4) . ?
N23 C8 1.333(3) . ?
N8 N9 1.404(3) . ?
N8 C3 1.344(3) . ?
N9 C4 1.348(3) . ?
N9 C5 1.348(3) . ?
N10 H10 0.90(3) . ?
N10 N11 1.410(3) . ?
N10 C4 1.347(3) . ?
N11 C5 1.307(3) . ?
N12 N13 1.382(3) . ?
N12 C3 1.388(3) . ?
N12 C5 1.357(3) . ?
N13 H13A 0.85(3) . ?
N13 H13B 0.99(4) . ?
N14 H14A 0.85(4) . ?
N14 H14B 0.83(4) . ?
N14 C3 1.326(3) . ?
N15 H15A 0.95(3) . ?
N15 H15B 0.86(3) . ?
N15 C4 1.327(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
C1 N1 N2 118.44(18) . . ?
C2 N2 N1 117.49(18) . . ?
N4 N3 C2 118.49(18) . . ?
N3 N4 C1 117.72(18) . . ?
N6 N5 C1 119.46(18) . . ?
O1 N6 N5 114.99(18) . . ?
O2 N6 O1 121.05(18) . . ?
O2 N6 N5 123.93(18) . . ?
N24 N7 C2 118.63(18) . . ?
O3 N24 O4 119.27(19) . . ?
O3 N24 N7 117.28(18) . . ?
O4 N24 N7 123.40(19) . . ?
N1 C1 N4 123.4(2) . . ?
N1 C1 N5 126.6(2) . . ?
N5 C1 N4 110.02(18) . . ?
N2 C2 N3 123.4(2) . . ?
N2 C2 N7 127.5(2) . . ?
N3 C2 N7 109.00(18) . . ?
C6 N16 N17 101.33(16) . . ?
C7 N17 N16 113.40(17) . . ?
C8 N17 N16 139.61(18) . . ?
C8 N17 C7 106.90(17) . . ?
N19 N18 H18 123.2(19) . . ?
C8 N18 H18 123.4(19) . . ?
C8 N18 N19 113.42(18) . . ?
C7 N19 N18 100.31(16) . . ?
C6 N20 N21 130.64(18) . . ?
C7 N20 N21 122.69(17) . . ?
C7 N20 C6 106.51(17) . . ?
N20 N21 H21A 109.6(19) . . ?
N20 N21 H21B 105(2) . . ?
H21A N21 H21B 113(3) . . ?
H22A N22 H22B 123(3) . . ?
C6 N22 H22A 116.5(18) . . ?
C6 N22 H22B 112.8(19) . . ?
H23A N23 H23B 120(3) . . ?
C8 N23 H23A 113(2) . . ?
C8 N23 H23B 121(2) . . ?
N16 C6 N20 113.34(18) . . ?
N16 C6 N22 125.1(2) . . ?
N22 C6 N20 121.42(19) . . ?
N17 C7 N20 105.39(17) . . ?
N19 C7 N17 114.56(19) . . ?
N19 C7 N20 140.0(2) . . ?
N18 C8 N17 104.80(18) . . ?
N23 C8 N17 128.3(2) . . ?
N23 C8 N18 126.8(2) . . ?
C3 N8 N9 100.27(17) . . ?
C4 N9 N8 138.4(2) . . ?
C5 N9 N8 114.01(18) . . ?
C5 N9 C4 107.54(19) . . ?
N11 N10 H10 122(2) . . ?
C4 N10 H10 125(2) . . ?
C4 N10 N11 112.82(18) . . ?
C5 N11 N10 100.70(18) . . ?
N13 N12 C3 121.82(19) . . ?
C5 N12 N13 131.26(19) . . ?
C5 N12 C3 106.09(18) . . ?
N12 N13 H13A 109.6(19) . . ?
N12 N13 H13B 110(2) . . ?
H13A N13 H13B 115(3) . . ?
H14A N14 H14B 122(3) . . ?
C3 N14 H14A 119(2) . . ?
C3 N14 H14B 119(2) . . ?
H15A N15 H15B 125(3) . . ?
C4 N15 H15A 119.9(18) . . ?
C4 N15 H15B 115(2) . . ?
N8 C3 N12 113.8(2) . . ?
N14 C3 N8 127.9(2) . . ?
N14 C3 N12 118.2(2) . . ?
N10 C4 N9 104.54(19) . . ?
N15 C4 N9 127.5(2) . . ?
N15 C4 N10 127.9(2) . . ?
N9 C5 N12 105.79(19) . . ?
N11 C5 N9 114.39(19) . . ?
N11 C5 N12 139.8(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
N18 H18 N5 0.89(3) 1.87(3) 2.757(3) 175(3) . yes
N22 H22A O3 0.91(3) 2.57(3) 3.093(2) 117(2) 2_625 yes
N23 H23A O1 0.90(4) 2.10(4) 2.982(3) 165(3) . yes
N23 H23B O3 0.83(4) 2.01(4) 2.830(3) 165(3) 4_585 yes
N10 H10 O2 0.90(3) 2.37(3) 2.945(3) 121(2) 2_535 yes
N10 H10 N1 0.90(3) 1.92(3) 2.795(3) 164(3) 2_535 yes
N13 H13A N11 0.85(3) 2.23(3) 3.057(3) 166(3) 2 yes
N14 H14A O4 0.85(4) 1.91(4) 2.751(3) 170(3) 4_595 yes
N14 H14B O1 0.83(4) 2.31(4) 3.086(3) 156(3) . yes
N15 H15A O4 0.95(3) 2.06(3) 2.835(3) 138(3) 2_535 yes
N15 H15A N2 0.95(3) 2.26(3) 3.092(3) 146(2) 2_535 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 -8.5(3) . . . . ?
N1 N2 C2 N7 169.5(2) . . . . ?
N2 N1 C1 N4 8.2(3) . . . . ?
N2 N1 C1 N5 -170.4(2) . . . . ?
N3 N4 C1 N1 -9.0(3) . . . . ?
N3 N4 C1 N5 169.78(18) . . . . ?
N4 N3 C2 N2 7.7(3) . . . . ?
N4 N3 C2 N7 -170.61(18) . . . . ?
N6 N5 C1 N1 -9.1(3) . . . . ?
N6 N5 C1 N4 172.12(18) . . . . ?
N24 N7 C2 N2 14.4(3) . . . . ?
N24 N7 C2 N3 -167.37(18) . . . . ?
C1 N1 N2 C2 0.5(3) . . . . ?
C1 N5 N6 O1 169.37(19) . . . . ?
C1 N5 N6 O2 -12.7(3) . . . . ?
C2 N3 N4 C1 1.0(3) . . . . ?
C2 N7 N24 O3 -174.49(18) . . . . ?
C2 N7 N24 O4 7.9(3) . . . . ?
N16 N17 C7 N19 177.40(17) . . . . ?
N16 N17 C7 N20 -1.8(2) . . . . ?
N16 N17 C8 N18 -176.8(2) . . . . ?
N16 N17 C8 N23 0.7(4) . . . . ?
N17 N16 C6 N20 -0.8(2) . . . . ?
N17 N16 C6 N22 175.13(19) . . . . ?
N18 N19 C7 N17 0.4(2) . . . . ?
N18 N19 C7 N20 179.1(3) . . . . ?
N19 N18 C8 N17 0.8(2) . . . . ?
N19 N18 C8 N23 -176.7(2) . . . . ?
N21 N20 C6 N16 175.3(2) . . . . ?
N21 N20 C6 N22 -0.8(3) . . . . ?
N21 N20 C7 N17 -174.77(18) . . . . ?
N21 N20 C7 N19 6.4(4) . . . . ?
C6 N16 N17 C7 1.6(2) . . . . ?
C6 N16 N17 C8 177.7(2) . . . . ?
C6 N20 C7 N17 1.1(2) . . . . ?
C6 N20 C7 N19 -177.7(3) . . . . ?
C7 N17 C8 N18 -0.5(2) . . . . ?
C7 N17 C8 N23 177.0(2) . . . . ?
C7 N20 C6 N16 -0.2(2) . . . . ?
C7 N20 C6 N22 -176.29(19) . . . . ?
C8 N17 C7 N19 0.0(2) . . . . ?
C8 N17 C7 N20 -179.13(17) . . . . ?
C8 N18 N19 C7 -0.7(2) . . . . ?
N8 N9 C4 N10 178.5(2) . . . . ?
N8 N9 C4 N15 -0.5(4) . . . . ?
N8 N9 C5 N11 -178.80(19) . . . . ?
N8 N9 C5 N12 0.7(2) . . . . ?
N9 N8 C3 N12 -0.8(2) . . . . ?
N9 N8 C3 N14 -179.6(2) . . . . ?
N10 N11 C5 N9 -0.2(2) . . . . ?
N10 N11 C5 N12 -179.5(3) . . . . ?
N11 N10 C4 N9 0.1(2) . . . . ?
N11 N10 C4 N15 179.1(2) . . . . ?
N13 N12 C3 N8 171.9(2) . . . . ?
N13 N12 C3 N14 -9.1(3) . . . . ?
N13 N12 C5 N9 -170.6(2) . . . . ?
N13 N12 C5 N11 8.8(5) . . . . ?
C3 N8 N9 C4 -178.6(3) . . . . ?
C3 N8 N9 C5 0.0(2) . . . . ?
C3 N12 C5 N9 -1.1(2) . . . . ?
C3 N12 C5 N11 178.2(3) . . . . ?
C4 N9 C5 N11 0.3(3) . . . . ?
C4 N9 C5 N12 179.79(18) . . . . ?
C4 N10 N11 C5 0.0(2) . . . . ?
C5 N9 C4 N10 -0.2(2) . . . . ?
C5 N9 C4 N15 -179.2(2) . . . . ?
C5 N12 C3 N8 1.3(3) . . . . ?
C5 N12 C3 N14 -179.8(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 JS856-CY-DMSO
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.640
####################################################################### 
# 
# 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_js1123b
_database_code_depnum_ccdc_archive 'CCDC 2346398'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-08 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-11-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N8 O4, 2(C3 H7 N8), 2(H2 O)'
_chemical_formula_sum            'C8 H18 N24 O6'
_chemical_formula_weight         546.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H14N24O4
_chemical_oxdiff_usercomment     JS856
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.48693(15)
_cell_length_b                   11.5802(2)
_cell_length_c                   12.4606(2)
_cell_angle_alpha                104.8425(15)
_cell_angle_beta                 90.1568(15)
_cell_angle_gamma                98.5391(17)
_cell_volume                     1031.77(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7222
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9480
_cell_measurement_theta_min      3.6690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.300
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0172
0 0 1 0.0058
5 -3 0 0.0607
-5 3 -1 0.0677
-1 -1 8 0.0097
1 1 -8 0.0166
-1 -7 0 0.0381
1 7 -1 0.0279
-2 7 -3 0.0571
2 -7 -1 0.0444

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.023
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
-0.0003 0.0001 -0.9999 0.0056 0.0121 -0.1273
0.0003 -0.0001 0.9999 -0.0056 -0.0121 0.1273
4.5701 -3.3980 -0.3421 -0.2278 -0.9470 -0.2264
-4.6062 3.3931 -1.0655 0.2334 0.9712 0.0472
-0.7111 -0.7811 7.9331 -0.1823 0.0425 0.9823
0.7588 1.0055 -7.9518 0.2144 -0.0502 -0.9755
-1.4042 -6.6456 0.4545 -0.9493 0.2283 -0.2160
1.4660 6.7064 -1.1650 0.9643 -0.2318 0.1276
-1.9353 7.2397 -2.5037 0.8789 0.4770 0.0076
1.9520 -6.8846 -0.5221 -0.8140 -0.4412 -0.3777

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14362
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.325
_diffrn_reflns_theta_min         3.673
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  -7.00   0.50    0.40    --  -47.12   8.00 152.00   54
  2  ω   -121.00 -28.00   0.50    0.40    --  -47.12  -8.00 -22.00  186
  3  ω     60.00  99.00   0.50    0.40    --   47.12   8.00 152.00   78
  4  ω    -22.00  13.00   0.50    0.40    --   47.12  -8.00 -22.00   70
  5  ω    -67.00 -42.00   0.50    1.60    --  -91.75   8.00 152.00   50
  6  ω   -159.00-121.00   0.50    1.60    --  -91.75  -8.00 -22.00   76
  7  ω     94.00 168.00   0.50    1.60    --  113.25   8.00 152.00  148
  8  ω     40.00  67.00   0.50    1.60    --  113.25  -8.00 -22.00   54
  9  ω    -82.00 -47.00   0.50    0.40    --  -47.12 125.00-150.00   70
 10  ω    -45.00  24.00   0.50    0.40    --  -47.12  37.00 150.00  138
 11  ω    -19.00  34.00   0.50    0.40    --   47.12 -19.00  30.00  106
 12  ω     63.00 115.00   0.50    0.40    --   47.12  37.00  30.00  104
 13  ω     41.00  89.00   0.50    0.40    --   47.12-125.00-120.00   96
 14  ω    -27.00  31.00   0.50    0.40    --   47.12 -19.00 -90.00  116
 15  ω    -60.00 -35.00   0.50    1.60    --  -91.75  61.00 -60.00   50
 16  ω    -41.00 -16.00   0.50    1.60    --  -91.75  15.00 -90.00   50
 17  ω    -76.00 -38.00   0.50    1.60    --  -91.75 125.00  30.00   76
 18  ω    -47.00 -20.00   0.50    1.60    --  -91.75  45.00  30.00   54
 19  ω     43.00  69.00   0.50    1.60    --  113.25 -61.00 150.00   52
 20  ω    118.00 161.00   0.50    1.60    --  113.25  45.00  60.00   86
 21  ω    146.00 173.00   0.50    1.60    --  113.25  61.00  90.00   54
 22  ω     79.00 104.00   0.50    1.60    --  113.25 -94.00 -30.00   50
 23  ω     42.00  67.00   0.50    1.60    --  113.25 -61.00 -30.00   50
 24  ω     45.00  97.00   0.50    1.60    --  113.25 -94.00-120.00  104
 25  ω     43.00  69.00   0.50    1.60    --  113.25 -61.00 -60.00   52
 26  ω    105.00 177.00   0.50    1.60    --  113.25  30.00 -90.00  144
 27  ω     69.00 102.00   0.50    1.60    --  113.25 -94.00-180.00   66
 28  ω     42.00  67.00   0.50    1.60    --  113.25 -77.00-150.00   50
 29  ω     75.00 104.00   0.50    1.60    --  113.25 -94.00 120.00   58
 30  ω     42.00  76.00   0.50    1.60    --  113.25 -77.00  90.00   68
 31  ω    131.00 169.00   0.50    1.60    --  113.25  61.00   0.00   76
 32  ω     42.00  67.00   0.50    1.60    --  113.25 -77.00 -90.00   50
 33  ω     43.00  69.00   0.50    1.60    --  113.25 -61.00 -90.00   52
 34  ω    113.00 138.00   0.50    1.60    --  113.25  61.00  90.00   50
 35  ω     65.00 103.00   0.50    1.60    --  113.25 -94.00  30.00   76
 36  ω     48.00  74.00   0.50    1.60    --  113.25 -94.00 -30.00   52
 37  ω     49.00  74.00   0.50    1.60    --  113.25-125.00-180.00   50
 38  ω     75.00 103.00   0.50    1.60    --  113.25 -94.00-150.00   56
 39  ω     43.00  68.00   0.50    1.60    --  113.25 -61.00  90.00   50
 40  ω     71.00  96.00   0.50    1.60    --  113.25 -94.00  60.00   50
 41  ω     42.00  68.00   0.50    1.60    --  113.25 -94.00  60.00   52
 42  ω     42.00 101.00   0.50    1.60    --  113.25 -94.00 -60.00  118
 43  ω     78.00 103.00   0.50    1.60    --  113.25 -94.00  90.00   50
 44  ω     51.00 103.00   0.50    1.60    --  113.25 -94.00 150.00  104
 45  ω    142.00 176.00   0.50    1.60    --  113.25  45.00  30.00   68
 46  ω    106.00 151.00   0.50    1.60    --  113.25  30.00-180.00   90
 47  ω    101.00 135.00   0.50    1.60    --  113.25  45.00  30.00   68
 48  ω    112.00 176.00   0.50    1.60    --  113.25  15.00   0.00  128
 49  ω     44.00  69.00   0.50    1.60    --  113.25 -61.00   0.00   50
 50  ω     48.00 100.00   0.50    1.60    --  113.25 -94.00 -90.00  104
 51  ω     48.00  78.00   0.50    1.60    --  113.25 -77.00  60.00   60
 52  ω     42.00  96.00   0.50    1.60    --  113.25 -94.00   0.00  108
 53  ω    123.00 148.00   0.50    1.60    --  113.25  77.00 -60.00   50
 54  ω     47.00  75.00   0.50    1.60    --  113.25-125.00-120.00   56
;
_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      0.0480939000
_diffrn_orient_matrix_UB_12      0.1323012000
_diffrn_orient_matrix_UB_13      -0.0056417000
_diffrn_orient_matrix_UB_21      -0.2024719000
_diffrn_orient_matrix_UB_22      0.0075977000
_diffrn_orient_matrix_UB_23      -0.0120453000
_diffrn_orient_matrix_UB_31      -0.0080922000
_diffrn_orient_matrix_UB_32      0.0429173000
_diffrn_orient_matrix_UB_33      0.1273257000
_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_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3613
_reflns_number_total             4394
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.94a 64-bit (release 20-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         4394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.2713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(O1S)=Sof(H1SA)=Sof(H1SB)=1-FVAR(1)
 Sof(O1B)=Sof(H1BA)=Sof(H1BB)=FVAR(1)
3.a Free rotating group:
 O1S(H1SA,H1SB), O1B(H1BA,H1BB)
;
_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
O4 O 0.03318(17) 0.61192(12) -0.38697(9) 0.0341(3) Uani 1 1 d . . . . .
O2 O -0.47076(15) 0.82296(11) 0.31279(9) 0.0299(3) Uani 1 1 d . . . . .
O1 O -0.21655(15) 0.77122(11) 0.24773(10) 0.0315(3) Uani 1 1 d . . . . .
O3 O 0.12312(16) 0.64169(12) -0.21468(10) 0.0337(3) Uani 1 1 d . . . . .
N23 N -0.14312(17) 0.69392(12) -0.25899(11) 0.0259(3) Uani 1 1 d . . . . .
N19 N -0.33888(18) 0.77871(12) -0.13919(11) 0.0259(3) Uani 1 1 d . . . . .
N22 N -0.36854(17) 0.79647(12) 0.23216(11) 0.0255(3) Uani 1 1 d . . . . .
N24 N 0.00728(18) 0.64846(12) -0.28479(11) 0.0262(3) Uani 1 1 d . . . . .
N18 N -0.11211(18) 0.69255(12) -0.06536(11) 0.0249(3) Uani 1 1 d . . . . .
N21 N -0.43638(17) 0.80098(12) 0.13553(11) 0.0249(3) Uani 1 1 d . . . . .
N17 N -0.18848(18) 0.71852(12) 0.03356(11) 0.0248(3) Uani 1 1 d . . . . .
N20 N -0.41119(17) 0.80379(11) -0.04378(11) 0.0253(3) Uani 1 1 d . . . . .
C8 C -0.1892(2) 0.72114(13) -0.14974(13) 0.0232(3) Uani 1 1 d . . . . .
C7 C -0.33575(19) 0.77200(13) 0.04322(13) 0.0228(3) Uani 1 1 d . . . . .
N15 N 0.63607(19) 0.11156(14) 0.23368(14) 0.0310(3) Uani 1 1 d . . . . .
H15A H 0.601(3) 0.129(2) 0.172(2) 0.045(6) Uiso 1 1 d . . . . .
H15B H 0.591(3) 0.1370(19) 0.2949(19) 0.031(5) Uiso 1 1 d . . . . .
N16 N 1.2421(2) -0.08395(13) 0.06086(12) 0.0289(3) Uani 1 1 d . . . . .
H16A H 1.341(3) -0.116(2) 0.0478(18) 0.040(6) Uiso 1 1 d . . . . .
H16B H 1.188(3) -0.069(2) 0.003(2) 0.043(6) Uiso 1 1 d . . . . .
N11 N 0.86309(18) 0.05464(13) 0.33101(12) 0.0286(3) Uani 1 1 d . . . . .
N14 N 0.7771(2) 0.07441(19) 0.43128(13) 0.0401(4) Uani 1 1 d . . . . .
H14A H 0.850(3) 0.1274(17) 0.4809(16) 0.020(4) Uiso 1 1 d . . . . .
H14B H 0.740(6) 0.001(4) 0.453(3) 0.110(13) Uiso 1 1 d . . . . .
N12 N 0.89167(17) 0.03729(12) 0.14626(11) 0.0250(3) Uani 1 1 d . . . . .
N13 N 1.03487(17) -0.00109(11) 0.19412(11) 0.0238(3) Uani 1 1 d . . . . .
N10 N 1.14552(19) -0.03305(13) 0.34844(11) 0.0293(3) Uani 1 1 d . . . . .
N9 N 1.24824(18) -0.07082(12) 0.25598(11) 0.0262(3) Uani 1 1 d . . . . .
H9 H 1.348(4) -0.105(2) 0.265(2) 0.047(6) Uiso 1 1 d . . . . .
C6 C 1.1815(2) -0.05413(13) 0.16237(13) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.7923(2) 0.07036(14) 0.23414(13) 0.0249(3) Uani 1 1 d . . . . .
C4 C 1.0188(2) 0.00749(14) 0.30356(13) 0.0264(3) Uani 1 1 d . . . . .
N5 N 0.30846(16) 0.57139(11) 0.16795(10) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.08551(17) 0.64908(12) 0.26713(11) 0.0245(3) Uani 1 1 d . . . . .
N7 N 0.60479(19) 0.48265(14) 0.32824(12) 0.0289(3) Uani 1 1 d . . . . .
H7A H 0.685(3) 0.447(2) 0.2886(19) 0.038(6) Uiso 1 1 d . . . . .
H7B H 0.591(3) 0.485(2) 0.398(2) 0.041(6) Uiso 1 1 d . . . . .
N6 N 0.3192(2) 0.57507(15) 0.45198(11) 0.0283(3) Uani 1 1 d . . . . .
H6A H 0.350(3) 0.647(2) 0.4917(18) 0.034(5) Uiso 1 1 d . . . . .
H6B H 0.212(4) 0.543(2) 0.4597(19) 0.043(6) Uiso 1 1 d . . . . .
N3 N 0.34206(17) 0.57121(12) 0.34019(10) 0.0228(3) Uani 1 1 d . . . . .
N1 N 0.07075(18) 0.64718(12) 0.15407(11) 0.0240(3) Uani 1 1 d . . . . .
H1 H -0.022(3) 0.6717(18) 0.1310(17) 0.031(5) Uiso 1 1 d . . . . .
N4 N 0.46683(16) 0.51975(11) 0.17111(10) 0.0221(3) Uani 1 1 d . . . . .
N8 N 0.22737(19) 0.58707(12) -0.01393(11) 0.0255(3) Uani 1 1 d . . . . .
H8A H 0.321(3) 0.5552(19) -0.0465(17) 0.034(5) Uiso 1 1 d . . . . .
H8B H 0.152(3) 0.618(2) -0.0556(18) 0.038(6) Uiso 1 1 d . . . . .
C2 C 0.4786(2) 0.52139(13) 0.27847(12) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.2331(2) 0.60246(13) 0.26811(12) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.20367(19) 0.60104(12) 0.09406(12) 0.0213(3) Uani 1 1 d . . . . .
O1S O 0.4686(9) 0.2046(5) 0.4464(7) 0.048(2) Uani 0.316(10) 1 d G . P A 1
H1SA H 0.463468 0.227483 0.385316 0.072 Uiso 0.316(10) 1 d G U P A 1
H1SB H 0.356859 0.194458 0.465564 0.072 Uiso 0.316(10) 1 d G U P A 1
O2S O 0.1097(2) 0.24304(15) 0.52146(12) 0.0471(4) Uani 1 1 d . . . . .
H2SA H 0.084(4) 0.305(3) 0.490(2) 0.070(9) Uiso 1 1 d . . . . .
H2SB H 0.114(4) 0.274(3) 0.602(3) 0.075(9) Uiso 1 1 d . . . . .
O1B O 0.4172(3) 0.2265(2) 0.3988(2) 0.0309(8) Uani 0.684(10) 1 d G . P A 2
H1BA H 0.354170 0.252604 0.353785 0.046 Uiso 0.684(10) 1 d G U P A 2
H1BB H 0.344269 0.217357 0.451239 0.046 Uiso 0.684(10) 1 d G U P A 2


_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
O4 N24 1.2599(18) . ?
O2 N22 1.2670(18) . ?
O1 N22 1.2429(17) . ?
O3 N24 1.2540(17) . ?
N23 N24 1.3190(19) . ?
N23 C8 1.374(2) . ?
N19 N20 1.290(2) . ?
N19 C8 1.377(2) . ?
N22 N21 1.3219(18) . ?
N18 N17 1.3423(19) . ?
N18 C8 1.3342(19) . ?
N21 C7 1.373(2) . ?
N17 C7 1.334(2) . ?
N20 C7 1.3757(19) . ?
N15 H15A 0.89(3) . ?
N15 H15B 0.84(2) . ?
N15 C5 1.328(2) . ?
N16 H16A 0.87(2) . ?
N16 H16B 0.89(3) . ?
N16 C6 1.323(2) . ?
N11 N14 1.389(2) . ?
N11 C5 1.382(2) . ?
N11 C4 1.367(2) . ?
N14 H14A 0.87(2) . ?
N14 H14B 0.96(4) . ?
N12 N13 1.4058(17) . ?
N12 C5 1.332(2) . ?
N13 C6 1.348(2) . ?
N13 C4 1.349(2) . ?
N10 N9 1.3988(19) . ?
N10 C4 1.303(2) . ?
N9 H9 0.92(3) . ?
N9 C6 1.337(2) . ?
N5 N4 1.4097(16) . ?
N5 C1 1.356(2) . ?
N5 C3 1.3487(18) . ?
N2 N1 1.4071(18) . ?
N2 C1 1.301(2) . ?
N7 H7A 0.86(2) . ?
N7 H7B 0.88(3) . ?
N7 C2 1.321(2) . ?
N6 H6A 0.85(2) . ?
N6 H6B 0.85(3) . ?
N6 N3 1.3940(18) . ?
N3 C2 1.386(2) . ?
N3 C1 1.3615(19) . ?
N1 H1 0.86(2) . ?
N1 C3 1.339(2) . ?
N4 C2 1.336(2) . ?
N8 H8A 0.89(2) . ?
N8 H8B 0.93(2) . ?
N8 C3 1.329(2) . ?
O1S H1SA 0.8700 . ?
O1S H1SB 0.8699 . ?
O2S H2SA 0.94(3) . ?
O2S H2SB 0.98(3) . ?
O1B H1BA 0.8696 . ?
O1B H1BB 0.8700 . ?

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
N24 N23 C8 118.58(13) . . ?
N20 N19 C8 118.57(13) . . ?
O2 N22 N21 114.55(12) . . ?
O1 N22 O2 120.26(13) . . ?
O1 N22 N21 125.18(13) . . ?
O4 N24 N23 116.20(13) . . ?
O3 N24 O4 119.69(13) . . ?
O3 N24 N23 124.10(13) . . ?
C8 N18 N17 117.82(13) . . ?
N22 N21 C7 118.51(12) . . ?
C7 N17 N18 118.93(13) . . ?
N19 N20 C7 118.74(13) . . ?
N23 C8 N19 109.25(13) . . ?
N18 C8 N23 127.40(14) . . ?
N18 C8 N19 123.25(14) . . ?
N21 C7 N20 109.94(13) . . ?
N17 C7 N21 127.39(14) . . ?
N17 C7 N20 122.65(14) . . ?
H15A N15 H15B 122(2) . . ?
C5 N15 H15A 118.0(16) . . ?
C5 N15 H15B 117.7(15) . . ?
H16A N16 H16B 117(2) . . ?
C6 N16 H16A 121.4(15) . . ?
C6 N16 H16B 122.0(15) . . ?
C5 N11 N14 124.17(14) . . ?
C4 N11 N14 129.34(14) . . ?
C4 N11 C5 106.25(13) . . ?
N11 N14 H14A 107.7(12) . . ?
N11 N14 H14B 112(2) . . ?
H14A N14 H14B 112(3) . . ?
C5 N12 N13 101.12(12) . . ?
C6 N13 N12 139.10(14) . . ?
C6 N13 C4 107.26(13) . . ?
C4 N13 N12 113.39(13) . . ?
C4 N10 N9 100.49(13) . . ?
N10 N9 H9 118.2(15) . . ?
C6 N9 N10 113.55(13) . . ?
C6 N9 H9 128.2(15) . . ?
N16 C6 N13 127.20(14) . . ?
N16 C6 N9 128.52(15) . . ?
N9 C6 N13 104.27(13) . . ?
N15 C5 N11 120.35(15) . . ?
N15 C5 N12 125.88(15) . . ?
N12 C5 N11 113.74(13) . . ?
N13 C4 N11 105.50(13) . . ?
N10 C4 N11 140.04(16) . . ?
N10 C4 N13 114.40(15) . . ?
C1 N5 N4 113.58(11) . . ?
C3 N5 N4 139.39(13) . . ?
C3 N5 C1 107.03(12) . . ?
C1 N2 N1 100.17(12) . . ?
H7A N7 H7B 124(2) . . ?
C2 N7 H7A 118.9(15) . . ?
C2 N7 H7B 116.6(16) . . ?
H6A N6 H6B 115(2) . . ?
N3 N6 H6A 110.1(15) . . ?
N3 N6 H6B 109.0(16) . . ?
C2 N3 N6 124.10(12) . . ?
C1 N3 N6 129.09(13) . . ?
C1 N3 C2 106.55(12) . . ?
N2 N1 H1 118.4(14) . . ?
C3 N1 N2 113.67(12) . . ?
C3 N1 H1 127.9(14) . . ?
C2 N4 N5 100.73(11) . . ?
H8A N8 H8B 118.3(19) . . ?
C3 N8 H8A 121.3(14) . . ?
C3 N8 H8B 120.0(13) . . ?
N7 C2 N3 119.46(14) . . ?
N7 C2 N4 126.73(15) . . ?
N4 C2 N3 113.81(13) . . ?
N5 C1 N3 105.32(13) . . ?
N2 C1 N5 114.76(13) . . ?
N2 C1 N3 139.91(14) . . ?
N1 C3 N5 104.37(13) . . ?
N8 C3 N5 127.61(14) . . ?
N8 C3 N1 128.02(14) . . ?
H1SA O1S H1SB 104.5 . . ?
H2SA O2S H2SB 108(2) . . ?
H1BA O1B H1BB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N15 H15A N19 0.89(3) 2.45(3) 3.0892(19) 129(2) 2_565 yes
N15 H15B O1S 0.84(2) 2.12(2) 2.952(6) 178(2) . yes
N15 H15B O1B 0.84(2) 2.04(2) 2.820(3) 155(2) . yes
N16 H16B N12 0.89(3) 2.09(3) 2.9692(19) 169(2) 2_755 yes
N14 H14A O2S 0.87(2) 2.17(2) 2.948(3) 148.6(16) 1_655 yes
N9 H9 O2 0.92(3) 1.86(3) 2.7653(18) 168(2) 1_745 yes
N7 H7A O3 0.86(2) 1.99(2) 2.8405(19) 172(2) 2_665 yes
N7 H7B N6 0.88(3) 2.28(3) 3.0517(19) 147(2) 2_666 yes
N6 H6A O1S 0.85(2) 2.01(2) 2.788(5) 153(2) 2_666 yes
N6 H6A O1B 0.85(2) 2.29(2) 3.013(3) 143(2) 2_666 yes
N6 H6B O4 0.85(3) 2.37(2) 2.9412(19) 124.6(19) 1_556 yes
N1 H1 O1 0.86(2) 2.29(2) 2.8503(18) 123.2(17) . yes
N1 H1 N17 0.86(2) 1.96(2) 2.7929(18) 161.2(19) . yes
N8 H8B O3 0.93(2) 2.09(2) 2.8658(17) 140.7(18) . yes
O1S H1SB O2S 0.87 2.08 2.907(6) 157.6 . yes
O2S H2SA O4 0.94(3) 2.06(3) 2.956(2) 159(3) 2_565 yes
O2S H2SB O1 0.98(3) 2.23(3) 3.0345(19) 139(2) 2_566 yes
O2S H2SB N2 0.98(3) 2.31(3) 3.084(2) 135(2) 2_566 yes
O1B H1BA N23 0.87 2.22 3.076(4) 167.6 2_565 yes
O1B H1BB O2S 0.87 1.99 2.770(2) 148.3 . 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
O2 N22 N21 C7 -179.12(13) . . . . ?
O1 N22 N21 C7 2.3(2) . . . . ?
N19 N20 C7 N21 -177.16(12) . . . . ?
N19 N20 C7 N17 1.5(2) . . . . ?
N22 N21 C7 N17 12.9(2) . . . . ?
N22 N21 C7 N20 -168.54(12) . . . . ?
N24 N23 C8 N19 173.75(13) . . . . ?
N24 N23 C8 N18 -9.7(2) . . . . ?
N18 N17 C7 N21 177.15(13) . . . . ?
N18 N17 C7 N20 -1.2(2) . . . . ?
N17 N18 C8 N23 -174.13(14) . . . . ?
N17 N18 C8 N19 2.0(2) . . . . ?
N20 N19 C8 N23 174.98(13) . . . . ?
N20 N19 C8 N18 -1.7(2) . . . . ?
C8 N23 N24 O4 172.01(13) . . . . ?
C8 N23 N24 O3 -9.0(2) . . . . ?
C8 N19 N20 C7 0.0(2) . . . . ?
C8 N18 N17 C7 -0.5(2) . . . . ?
N14 N11 C5 N15 2.9(3) . . . . ?
N14 N11 C5 N12 -175.14(16) . . . . ?
N14 N11 C4 N13 175.25(17) . . . . ?
N14 N11 C4 N10 -1.8(3) . . . . ?
N12 N13 C6 N16 3.7(3) . . . . ?
N12 N13 C6 N9 -175.35(16) . . . . ?
N12 N13 C4 N11 -1.05(17) . . . . ?
N12 N13 C4 N10 176.86(13) . . . . ?
N13 N12 C5 N15 -178.23(15) . . . . ?
N13 N12 C5 N11 -0.28(16) . . . . ?
N10 N9 C6 N16 -177.30(15) . . . . ?
N10 N9 C6 N13 1.78(17) . . . . ?
N9 N10 C4 N11 176.4(2) . . . . ?
N9 N10 C4 N13 -0.42(18) . . . . ?
C6 N13 C4 N11 -176.38(12) . . . . ?
C6 N13 C4 N10 1.53(19) . . . . ?
C5 N11 C4 N13 0.80(17) . . . . ?
C5 N11 C4 N10 -176.2(2) . . . . ?
C5 N12 N13 C6 174.01(17) . . . . ?
C5 N12 N13 C4 0.83(16) . . . . ?
C4 N11 C5 N15 177.75(14) . . . . ?
C4 N11 C5 N12 -0.32(18) . . . . ?
C4 N13 C6 N16 177.19(15) . . . . ?
C4 N13 C6 N9 -1.90(16) . . . . ?
C4 N10 N9 C6 -0.88(17) . . . . ?
N5 N4 C2 N7 180.00(15) . . . . ?
N5 N4 C2 N3 -0.86(15) . . . . ?
N2 N1 C3 N5 0.16(16) . . . . ?
N2 N1 C3 N8 179.99(14) . . . . ?
N6 N3 C2 N7 -5.4(2) . . . . ?
N6 N3 C2 N4 175.42(14) . . . . ?
N6 N3 C1 N5 -174.62(14) . . . . ?
N6 N3 C1 N2 4.2(3) . . . . ?
N1 N2 C1 N5 -0.62(16) . . . . ?
N1 N2 C1 N3 -179.39(18) . . . . ?
N4 N5 C1 N2 -179.25(12) . . . . ?
N4 N5 C1 N3 -0.07(16) . . . . ?
N4 N5 C3 N1 179.52(15) . . . . ?
N4 N5 C3 N8 -0.3(3) . . . . ?
C2 N3 C1 N5 -0.44(15) . . . . ?
C2 N3 C1 N2 178.40(19) . . . . ?
C1 N5 N4 C2 0.56(15) . . . . ?
C1 N5 C3 N1 -0.52(15) . . . . ?
C1 N5 C3 N8 179.66(14) . . . . ?
C1 N2 N1 C3 0.27(16) . . . . ?
C1 N3 C2 N7 -179.91(14) . . . . ?
C1 N3 C2 N4 0.87(17) . . . . ?
C3 N5 N4 C2 -179.47(16) . . . . ?
C3 N5 C1 N2 0.77(17) . . . . ?
C3 N5 C1 N3 179.95(12) . . . . ?

_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 js856
_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_js424bb
_database_code_depnum_ccdc_archive 'CCDC 2350606'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-23 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2024-04-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C4 N6 O9), 4(C3 H7 N8)'
_chemical_formula_sum            'C20 H28 N44 O18'
_chemical_formula_weight         1172.86
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H14N22O9
_chemical_oxdiff_usercomment     'JS1000 green needle'
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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   20.2501(8)
_cell_length_b                   5.35469(14)
_cell_length_c                   38.7326(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4199.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5738
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.6940
_cell_measurement_theta_min      4.3580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.419
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.96a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.0860
0 1 1 0.0860
0 0 1 0.0115
0 0 -1 0.0115
1 0 1 0.0149
-1 0 -1 0.0010

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.034
_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
0.0194 -1.0006 -1.0094 -0.2234 -0.1838 0.0282
-0.0194 1.0006 1.0094 0.2234 0.1838 -0.0282
0.0016 -0.0001 1.0003 -0.0024 0.0171 0.0359
-0.0016 0.0001 -1.0003 0.0024 -0.0171 -0.0359
1.0016 -0.0009 0.9941 0.0440 -0.0360 0.0643
-1.0016 0.0009 -0.9941 -0.0440 0.0360 -0.0643

_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  0.0879
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            25412
_diffrn_reflns_point_group_measured_fraction_full 0.789
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.098
_diffrn_reflns_theta_min         4.367
_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 0.998
_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    -60.00  -5.00   0.50    1.00    --  -47.94 108.00  84.00  110
  2  ω    -39.00  -7.00   0.50    1.00    --  -47.94  34.00  -3.00   64
  3  ω     12.00  39.00   0.50    1.00    --   47.94 -34.00-161.00   54
  4  ω     46.00 103.00   0.50    4.00    --  113.25-108.00 -12.00  114
  5  ω    132.00 174.00   0.50    4.00    --  113.25  94.00-172.00   84
  6  ω    106.00 143.00   0.50    4.00    --  113.25  34.00  -3.00   74
  7  ω    -18.00  21.00   0.50    1.00    --  -47.94  37.00   0.00   78
  8  ω    -30.00  20.00   0.50    1.00    --  -47.94  19.00 -90.00  100
  9  ω     43.00  68.00   0.50    4.00    --  113.25 -61.00 -30.00   50
 10  ω     50.00  77.00   0.50    4.00    --  113.25 -94.00  60.00   54
 11  ω    131.00 172.00   0.50    4.00    --  113.25  30.00-180.00   82
 12  ω     72.00  98.00   0.50    4.00    --  113.25-125.00  60.00   52
 13  ω     73.00  98.00   0.50    4.00    --  113.25 -77.00 -60.00   50
 14  ω     49.00  80.00   0.50    4.00    --  113.25 -77.00 -30.00   62
 15  ω     42.00  71.00   0.50    4.00    --  113.25 -77.00 -90.00   58
 16  ω     65.00  90.00   0.50    4.00    --  113.25 -77.00  30.00   50
 17  ω     42.00  68.00   0.50    4.00    --  113.25 -77.00 -60.00   52
 18  ω     50.00  96.00   0.50    4.00    --  113.25 -77.00  90.00   92
 19  ω    106.00 153.00   0.50    4.00    --  113.25  61.00 120.00   94
 20  ω     47.00  87.00   0.50    4.00    --  113.25 -77.00-180.00   80
 21  ω     46.00  96.00   0.50    4.00    --  113.25-125.00 150.00  100
 22  ω    129.00 155.00   0.50    4.00    --  113.25  61.00  30.00   52
 23  ω     98.00 124.00   0.50    4.00    --  113.25 125.00-120.00   52
 24  ω    153.00 178.00   0.50    4.00    --  113.25 125.00-120.00   50
 25  ω     95.00 121.00   0.50    4.00    --  113.25 -85.00  40.78   52
 26  ω     76.00 102.00   0.50    4.00    --  113.25 -94.00  75.00   52
 27  ω     47.00  84.00   0.50    4.00    --  113.25-125.00-150.00   74
 28  ω    113.00 152.00   0.50    4.00    --  113.25  77.00   0.00   78
 29  ω     69.00  95.00   0.50    4.00    --  113.25 -94.00  30.00   52
 30  ω     43.00  68.00   0.50    4.00    --  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      0.0466233000
_diffrn_orient_matrix_UB_12      0.2267047000
_diffrn_orient_matrix_UB_13      -0.0024799000
_diffrn_orient_matrix_UB_21      -0.0528670000
_diffrn_orient_matrix_UB_22      0.1653776000
_diffrn_orient_matrix_UB_23      0.0171614000
_diffrn_orient_matrix_UB_31      0.0285722000
_diffrn_orient_matrix_UB_32      -0.0637193000
_diffrn_orient_matrix_UB_33      0.0357988000
_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         0.523
_reflns_Friedel_fraction_full    0.572
_reflns_Friedel_fraction_max     0.530
_reflns_number_gt                5732
_reflns_number_total             6968
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     744
_refine_ls_number_reflns         6968
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.033
_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)+(0.0345P)²+5.8123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4(5)
 0.6(5)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
3.a Rotating group:
 N6D(H6DA,H6DB), N6C(H6CA,H6CB), N6E(H6EA,H6EB), N6B(H6BA,H6BB)
3.b Aromatic/amide H refined with riding coordinates:
 N1D(H1D), N1C(H1C), N1E(H1E), N1B(H1B)
3.c X=CH2 refined with riding coordinates:
 N7D(H7DA,H7DB), N8D(H8DA,H8DB), N7C(H7CA,H7CB), N8C(H8CA,H8CB), N7E(H7EA,
 H7EB), N8E(H8EA,H8EB), N7B(H7BA,H7BB), N8B(H8BA,H8BB)
;
_atom_sites_solution_hydrogens   mixed
_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 0.8070(2) 0.9524(7) 0.37403(10) 0.0156(8) Uani 1 1 d . . . . .
O2 O 0.9238(2) 1.4949(9) 0.33976(12) 0.0247(9) Uani 1 1 d . . . . .
O3 O 0.8863(3) 1.4837(8) 0.28695(11) 0.0255(10) Uani 1 1 d . . . . .
O4 O 0.7784(2) 1.2438(9) 0.27906(11) 0.0237(10) Uani 1 1 d . . . . .
O5 O 0.7809(3) 0.8924(9) 0.30741(12) 0.0292(11) Uani 1 1 d . . . . .
O6 O 0.8208(3) 1.0788(9) 0.46462(12) 0.0283(11) Uani 1 1 d . . . . .
O7 O 0.7447(2) 0.8287(8) 0.48322(10) 0.0194(9) Uani 1 1 d . . . . .
O8 O 0.7125(2) 0.4666(8) 0.44248(11) 0.0227(9) Uani 1 1 d . . . . .
O9 O 0.7675(2) 0.4459(8) 0.39424(10) 0.0214(9) Uani 1 1 d . . . . .
N1 N 0.9117(3) 1.0638(10) 0.37665(12) 0.0189(10) Uani 1 1 d . . . . .
N2 N 0.8960(3) 0.9264(10) 0.40636(12) 0.0194(10) Uani 1 1 d . . . . .
N3 N 0.8863(3) 1.4021(10) 0.31728(13) 0.0202(11) Uani 1 1 d . . . . .
N4 N 0.7992(3) 1.1109(10) 0.30289(12) 0.0210(11) Uani 1 1 d . . . . .
N5 N 0.7847(3) 0.8899(10) 0.46091(12) 0.0178(10) Uani 1 1 d . . . . .
N6 N 0.7552(3) 0.5494(9) 0.42275(12) 0.0176(10) Uani 1 1 d . . . . .
C1 C 0.8574(3) 1.0728(11) 0.35859(14) 0.0165(11) Uani 1 1 d . . . . .
C2 C 0.8353(3) 0.8673(11) 0.40421(14) 0.0135(10) Uani 1 1 d . . . . .
C3 C 0.8456(3) 1.2047(11) 0.32632(14) 0.0169(11) Uani 1 1 d . . . . .
C4 C 0.7933(3) 0.7561(11) 0.43035(14) 0.0155(11) Uani 1 1 d . . . . .
O1A O 0.9757(2) 0.7073(7) 0.62870(10) 0.0155(8) Uani 1 1 d . . . . .
O2A O 0.9326(2) 1.0031(8) 0.71918(11) 0.0212(9) Uani 1 1 d . . . . .
O3A O 0.8407(2) 0.8057(9) 0.72733(10) 0.0203(9) Uani 1 1 d . . . . .
O4A O 0.8260(2) 0.4241(9) 0.68748(12) 0.0275(10) Uani 1 1 d . . . . .
O5A O 0.8589(2) 0.4908(8) 0.63465(10) 0.0198(9) Uani 1 1 d . . . . .
O6A O 1.1443(2) 1.0518(9) 0.60305(11) 0.0213(9) Uani 1 1 d . . . . .
O7A O 1.1446(2) 0.9194(9) 0.55005(11) 0.0239(10) Uani 1 1 d . . . . .
O8A O 1.0843(3) 0.4848(9) 0.54536(12) 0.0278(10) Uani 1 1 d . . . . .
O9A O 0.9858(2) 0.5198(8) 0.56677(11) 0.0223(9) Uani 1 1 d . . . . .
N1A N 0.9737(3) 1.0720(10) 0.65550(13) 0.0206(11) Uani 1 1 d . . . . .
N2A N 1.0218(3) 1.0780(9) 0.62992(13) 0.0198(10) Uani 1 1 d . . . . .
N3A N 0.8891(3) 0.8534(9) 0.70901(12) 0.0169(10) Uani 1 1 d . . . . .
N4A N 0.8585(2) 0.5459(9) 0.66623(12) 0.0151(10) Uani 1 1 d . . . . .
N5A N 1.1207(3) 0.9203(9) 0.57924(12) 0.0172(10) Uani 1 1 d . . . . .
N6A N 1.0451(3) 0.5888(10) 0.56502(13) 0.0192(10) Uani 1 1 d . . . . .
C1A C 0.9471(3) 0.8495(11) 0.65381(14) 0.0161(11) Uani 1 1 d . . . . .
C2A C 1.0217(3) 0.8640(11) 0.61442(14) 0.0150(11) Uani 1 1 d . . . . .
C3A C 0.8972(3) 0.7480(11) 0.67649(14) 0.0150(11) Uani 1 1 d . . . . .
C4A C 1.0639(3) 0.7816(11) 0.58664(14) 0.0165(11) Uani 1 1 d . . . . .
N1D N 0.5322(3) 1.1016(10) 0.33058(12) 0.0183(11) Uani 1 1 d . . . . .
H1D H 0.515845 1.239125 0.339629 0.022 Uiso 1 1 calc R U . . .
N2D N 0.5867(3) 0.9751(10) 0.34440(12) 0.0175(10) Uani 1 1 d . . . . .
N3D N 0.6318(3) 0.5935(9) 0.31566(12) 0.0159(10) Uani 1 1 d . . . . .
N4D N 0.5524(3) 0.5935(9) 0.27406(12) 0.0158(10) Uani 1 1 d . . . . .
N5D N 0.5457(3) 0.7897(9) 0.29766(12) 0.0155(10) Uani 1 1 d . . . . .
N6D N 0.6856(3) 0.5014(10) 0.33387(13) 0.0214(11) Uani 1 1 d . . . . .
H6DA H 0.673092 0.456578 0.354789 0.026 Uiso 1 1 d R U . . .
H6DB H 0.702111 0.370555 0.323019 0.026 Uiso 1 1 d R U . . .
N7D N 0.6336(3) 0.2752(9) 0.27335(12) 0.0182(10) Uani 1 1 d . . . . .
H7DA H 0.616303 0.200880 0.255232 0.022 Uiso 1 1 calc R U . . .
H7DB H 0.669367 0.213584 0.283086 0.022 Uiso 1 1 calc R U . . .
N8D N 0.4574(3) 1.0669(10) 0.28343(13) 0.0205(11) Uani 1 1 d . . . . .
H8DA H 0.435866 1.203908 0.289002 0.025 Uiso 1 1 calc R U . . .
H8DB H 0.445282 0.979971 0.265214 0.025 Uiso 1 1 calc R U . . .
C1D C 0.5920(3) 0.7895(11) 0.32270(14) 0.0166(11) Uani 1 1 d . . . . .
C2D C 0.6059(3) 0.4806(11) 0.28601(14) 0.0162(11) Uani 1 1 d . . . . .
C3D C 0.5073(3) 0.9926(11) 0.30221(14) 0.0158(11) Uani 1 1 d . . . . .
N1C N 0.8874(3) 1.1114(9) 0.58156(12) 0.0167(10) Uani 1 1 d . . . . .
H1C H 0.906886 1.241375 0.591020 0.020 Uiso 1 1 calc R U . . .
N2C N 0.8320(3) 0.9933(9) 0.59602(12) 0.0190(11) Uani 1 1 d . . . . .
N3C N 0.7829(3) 0.6141(9) 0.56798(12) 0.0159(10) Uani 1 1 d . . . . .
N4C N 0.8570(3) 0.6154(9) 0.52366(11) 0.0145(9) Uani 1 1 d . . . . .
N5C N 0.8666(3) 0.8131(9) 0.54723(11) 0.0153(10) Uani 1 1 d . . . . .
N6C N 0.7330(3) 0.5127(10) 0.58835(13) 0.0181(10) Uani 1 1 d . . . . .
H6CA H 0.749029 0.471048 0.608786 0.022 Uiso 1 1 d R U . . .
H6CB H 0.700920 0.623167 0.591157 0.022 Uiso 1 1 d R U . . .
N7C N 0.7749(3) 0.3007(10) 0.52643(12) 0.0189(10) Uani 1 1 d . . . . .
H7CA H 0.788849 0.226402 0.507528 0.023 Uiso 1 1 calc R U . . .
H7CB H 0.740691 0.240203 0.537711 0.023 Uiso 1 1 calc R U . . .
N8C N 0.9573(3) 1.0738(9) 0.53213(13) 0.0201(11) Uani 1 1 d . . . . .
H8CA H 0.966627 0.987895 0.513380 0.024 Uiso 1 1 calc R U . . .
H8CB H 0.981268 1.204961 0.537659 0.024 Uiso 1 1 calc R U . . .
C1C C 0.8229(3) 0.8134(11) 0.57376(14) 0.0148(11) Uani 1 1 d . . . . .
C2C C 0.8053(3) 0.5041(11) 0.53792(13) 0.0166(12) Uani 1 1 d . . . . .
C3C C 0.9079(3) 1.0065(10) 0.55177(14) 0.0154(11) Uani 1 1 d . . . . .
N1E N 0.9010(3) 1.5683(9) 0.16245(12) 0.0154(10) Uani 1 1 d . . . . .
H1E H 0.916734 1.702889 0.152327 0.018 Uiso 1 1 calc R U . . .
N2E N 0.8457(3) 1.4397(9) 0.15042(12) 0.0167(10) Uani 1 1 d . . . . .
N3E N 0.8032(3) 1.0628(9) 0.18127(11) 0.0154(10) Uani 1 1 d . . . . .
N4E N 0.8836(3) 1.0744(9) 0.22179(12) 0.0157(10) Uani 1 1 d . . . . .
N5E N 0.8897(2) 1.2653(9) 0.19756(11) 0.0133(9) Uani 1 1 d . . . . .
N6E N 0.7483(3) 0.9709(9) 0.16326(12) 0.0184(10) Uani 1 1 d . . . . .
H6EA H 0.734299 0.832303 0.173218 0.022 Uiso 1 1 d R U . . .
H6EB H 0.716328 1.082764 0.163548 0.022 Uiso 1 1 d R U . . .
N7E N 0.8044(3) 0.7478(9) 0.22405(12) 0.0172(10) Uani 1 1 d . . . . .
H7EA H 0.822729 0.677870 0.242246 0.021 Uiso 1 1 calc R U . . .
H7EB H 0.768883 0.681233 0.214753 0.021 Uiso 1 1 calc R U . . .
N8E N 0.9800(3) 1.5477(9) 0.20841(12) 0.0172(10) Uani 1 1 d . . . . .
H8EA H 1.000970 1.682754 0.201528 0.021 Uiso 1 1 calc R U . . .
H8EB H 0.993638 1.466619 0.226847 0.021 Uiso 1 1 calc R U . . .
C1E C 0.8421(3) 1.2623(11) 0.17306(14) 0.0168(12) Uani 1 1 d . . . . .
C2E C 0.8305(3) 0.9541(10) 0.21059(14) 0.0147(11) Uani 1 1 d . . . . .
C3E C 0.9284(3) 1.4669(11) 0.19115(14) 0.0161(11) Uani 1 1 d . . . . .
N1B N 0.9981(3) 0.4136(10) 0.40753(11) 0.0160(10) Uani 1 1 d . . . . .
H1B H 0.981163 0.283995 0.396720 0.019 Uiso 1 1 calc R U . . .
N2B N 1.0513(3) 0.5532(10) 0.39459(12) 0.0177(10) Uani 1 1 d . . . . .
N3B N 1.0992(3) 0.9101(9) 0.42900(12) 0.0165(10) Uani 1 1 d . . . . .
N4B N 1.0253(3) 0.8638(9) 0.47223(12) 0.0157(10) Uani 1 1 d . . . . .
N5B N 1.0163(3) 0.6874(9) 0.44588(12) 0.0156(10) Uani 1 1 d . . . . .
N6B N 1.1562(3) 0.9993(10) 0.41302(12) 0.0167(10) Uani 1 1 d . . . . .
H6BA H 1.187131 0.882176 0.412971 0.020 Uiso 1 1 d R U . . .
H6BB H 1.147500 1.042555 0.391400 0.020 Uiso 1 1 d R U . . .
N7B N 1.1015(3) 1.1959(10) 0.47560(12) 0.0191(10) Uani 1 1 d . . . . .
H7BA H 1.084689 1.252496 0.495034 0.023 Uiso 1 1 calc R U . . .
H7BB H 1.135374 1.272458 0.466073 0.023 Uiso 1 1 calc R U . . .
N8B N 0.9268(3) 0.4103(10) 0.45715(13) 0.0193(10) Uani 1 1 d . . . . .
H8BA H 0.918170 0.478052 0.477351 0.023 Uiso 1 1 calc R U . . .
H8BB H 0.902922 0.284259 0.449652 0.023 Uiso 1 1 calc R U . . .
C1B C 1.0597(3) 0.7148(10) 0.41970(14) 0.0153(11) Uani 1 1 d . . . . .
C2B C 1.0755(3) 0.9928(11) 0.46050(13) 0.0149(11) Uani 1 1 d . . . . .
C3B C 0.9755(3) 0.4975(10) 0.43817(14) 0.0135(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.346(7) . ?
O1 C2 1.378(7) . ?
O2 N3 1.258(7) . ?
O3 N3 1.253(7) . ?
O4 N4 1.239(7) . ?
O5 N4 1.239(7) . ?
O6 N5 1.257(7) . ?
O7 N5 1.229(7) . ?
O8 N6 1.236(7) . ?
O9 N6 1.261(6) . ?
N1 N2 1.402(7) . ?
N1 C1 1.304(8) . ?
N2 C2 1.273(8) . ?
N3 C3 1.385(8) . ?
N4 C3 1.401(8) . ?
N5 C4 1.395(7) . ?
N6 C4 1.381(8) . ?
C1 C3 1.455(8) . ?
C2 C4 1.450(8) . ?
O1A C1A 1.364(7) . ?
O1A C2A 1.369(7) . ?
O2A N3A 1.255(7) . ?
O3A N3A 1.235(7) . ?
O4A N4A 1.239(7) . ?
O5A N4A 1.258(6) . ?
O6A N5A 1.255(7) . ?
O7A N5A 1.229(7) . ?
O8A N6A 1.233(7) . ?
O9A N6A 1.258(7) . ?
N1A N2A 1.391(7) . ?
N1A C1A 1.308(8) . ?
N2A C2A 1.294(8) . ?
N3A C3A 1.390(7) . ?
N4A C3A 1.394(8) . ?
N5A C4A 1.399(8) . ?
N6A C4A 1.383(8) . ?
C1A C3A 1.445(8) . ?
C2A C4A 1.444(8) . ?
N1D H1D 0.8800 . ?
N1D N2D 1.402(7) . ?
N1D C3D 1.343(8) . ?
N2D C1D 1.306(8) . ?
N3D N6D 1.389(7) . ?
N3D C1D 1.350(8) . ?
N3D C2D 1.400(7) . ?
N4D N5D 1.399(6) . ?
N4D C2D 1.324(8) . ?
N5D C1D 1.350(8) . ?
N5D C3D 1.347(8) . ?
N6D H6DA 0.8823 . ?
N6D H6DB 0.8827 . ?
N7D H7DA 0.8800 . ?
N7D H7DB 0.8800 . ?
N7D C2D 1.329(8) . ?
N8D H8DA 0.8800 . ?
N8D H8DB 0.8800 . ?
N8D C3D 1.308(8) . ?
N1C H1C 0.8800 . ?
N1C N2C 1.404(7) . ?
N1C C3C 1.348(7) . ?
N2C C1C 1.306(8) . ?
N3C N6C 1.392(7) . ?
N3C C1C 1.358(8) . ?
N3C C2C 1.381(7) . ?
N4C N5C 1.411(6) . ?
N4C C2C 1.326(8) . ?
N5C C1C 1.356(7) . ?
N5C C3C 1.343(8) . ?
N6C H6CA 0.8843 . ?
N6C H6CB 0.8851 . ?
N7C H7CA 0.8800 . ?
N7C H7CB 0.8800 . ?
N7C C2C 1.328(8) . ?
N8C H8CA 0.8800 . ?
N8C H8CB 0.8800 . ?
N8C C3C 1.308(8) . ?
N1E H1E 0.8800 . ?
N1E N2E 1.395(7) . ?
N1E C3E 1.356(7) . ?
N2E C1E 1.295(8) . ?
N3E N6E 1.401(7) . ?
N3E C1E 1.365(8) . ?
N3E C2E 1.391(7) . ?
N4E N5E 1.393(7) . ?
N4E C2E 1.326(8) . ?
N5E C1E 1.353(7) . ?
N5E C3E 1.357(8) . ?
N6E H6EA 0.8832 . ?
N6E H6EB 0.8826 . ?
N7E H7EA 0.8800 . ?
N7E H7EB 0.8800 . ?
N7E C2E 1.331(8) . ?
N8E H8EA 0.8800 . ?
N8E H8EB 0.8800 . ?
N8E C3E 1.314(8) . ?
N1B H1B 0.8800 . ?
N1B N2B 1.404(7) . ?
N1B C3B 1.349(7) . ?
N2B C1B 1.313(8) . ?
N3B N6B 1.395(7) . ?
N3B C1B 1.365(8) . ?
N3B C2B 1.383(7) . ?
N4B N5B 1.402(7) . ?
N4B C2B 1.311(8) . ?
N5B C1B 1.350(8) . ?
N5B C3B 1.344(8) . ?
N6B H6BA 0.8859 . ?
N6B H6BB 0.8866 . ?
N7B H7BA 0.8800 . ?
N7B H7BB 0.8800 . ?
N7B C2B 1.342(8) . ?
N8B H8BA 0.8800 . ?
N8B H8BB 0.8800 . ?
N8B C3B 1.316(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 102.8(4) . . ?
C1 N1 N2 105.6(5) . . ?
C2 N2 N1 107.2(5) . . ?
O2 N3 C3 119.0(5) . . ?
O3 N3 O2 120.7(5) . . ?
O3 N3 C3 120.2(5) . . ?
O4 N4 C3 120.3(5) . . ?
O5 N4 O4 123.1(5) . . ?
O5 N4 C3 116.5(5) . . ?
O6 N5 C4 115.9(5) . . ?
O7 N5 O6 121.2(5) . . ?
O7 N5 C4 122.8(5) . . ?
O8 N6 O9 121.5(5) . . ?
O8 N6 C4 123.1(5) . . ?
O9 N6 C4 115.3(5) . . ?
O1 C1 C3 119.3(5) . . ?
N1 C1 O1 112.5(5) . . ?
N1 C1 C3 128.1(6) . . ?
O1 C2 C4 119.0(5) . . ?
N2 C2 O1 111.9(5) . . ?
N2 C2 C4 128.5(5) . . ?
N3 C3 N4 120.6(5) . . ?
N3 C3 C1 119.4(5) . . ?
N4 C3 C1 119.5(5) . . ?
N5 C4 C2 117.1(5) . . ?
N6 C4 N5 121.5(5) . . ?
N6 C4 C2 120.5(5) . . ?
C1A O1A C2A 103.6(4) . . ?
C1A N1A N2A 105.9(5) . . ?
C2A N2A N1A 108.0(5) . . ?
O2A N3A C3A 117.4(5) . . ?
O3A N3A O2A 120.5(5) . . ?
O3A N3A C3A 122.0(5) . . ?
O4A N4A O5A 121.7(5) . . ?
O4A N4A C3A 121.2(5) . . ?
O5A N4A C3A 117.1(5) . . ?
O6A N5A C4A 117.4(5) . . ?
O7A N5A O6A 121.9(5) . . ?
O7A N5A C4A 120.6(5) . . ?
O8A N6A O9A 121.0(5) . . ?
O8A N6A C4A 122.3(6) . . ?
O9A N6A C4A 116.7(5) . . ?
O1A C1A C3A 121.4(5) . . ?
N1A C1A O1A 111.7(5) . . ?
N1A C1A C3A 126.8(5) . . ?
O1A C2A C4A 121.1(5) . . ?
N2A C2A O1A 110.9(5) . . ?
N2A C2A C4A 128.0(6) . . ?
N3A C3A N4A 120.4(5) . . ?
N3A C3A C1A 118.8(5) . . ?
N4A C3A C1A 120.8(5) . . ?
N5A C4A C2A 118.5(5) . . ?
N6A C4A N5A 119.9(5) . . ?
N6A C4A C2A 121.1(6) . . ?
N2D N1D H1D 123.3 . . ?
C3D N1D H1D 123.3 . . ?
C3D N1D N2D 113.4(5) . . ?
C1D N2D N1D 100.8(5) . . ?
N6D N3D C2D 123.8(5) . . ?
C1D N3D N6D 129.9(5) . . ?
C1D N3D C2D 106.2(5) . . ?
C2D N4D N5D 101.2(4) . . ?
C1D N5D N4D 113.7(5) . . ?
C3D N5D N4D 138.3(5) . . ?
C3D N5D C1D 107.9(5) . . ?
N3D N6D H6DA 109.7 . . ?
N3D N6D H6DB 109.7 . . ?
H6DA N6D H6DB 109.3 . . ?
H7DA N7D H7DB 120.0 . . ?
C2D N7D H7DA 120.0 . . ?
C2D N7D H7DB 120.0 . . ?
H8DA N8D H8DB 120.0 . . ?
C3D N8D H8DA 120.0 . . ?
C3D N8D H8DB 120.0 . . ?
N2D C1D N3D 140.4(6) . . ?
N2D C1D N5D 113.9(6) . . ?
N5D C1D N3D 105.6(5) . . ?
N4D C2D N3D 113.3(5) . . ?
N4D C2D N7D 126.5(5) . . ?
N7D C2D N3D 120.1(5) . . ?
N1D C3D N5D 104.0(5) . . ?
N8D C3D N1D 127.8(6) . . ?
N8D C3D N5D 128.2(5) . . ?
N2C N1C H1C 123.2 . . ?
C3C N1C H1C 123.2 . . ?
C3C N1C N2C 113.5(5) . . ?
C1C N2C N1C 100.5(5) . . ?
C1C N3C N6C 130.2(5) . . ?
C1C N3C C2C 106.2(5) . . ?
C2C N3C N6C 123.3(5) . . ?
C2C N4C N5C 100.1(4) . . ?
C1C N5C N4C 113.7(5) . . ?
C3C N5C N4C 138.4(5) . . ?
C3C N5C C1C 107.9(5) . . ?
N3C N6C H6CA 109.8 . . ?
N3C N6C H6CB 110.0 . . ?
H6CA N6C H6CB 109.1 . . ?
H7CA N7C H7CB 120.0 . . ?
C2C N7C H7CA 120.0 . . ?
C2C N7C H7CB 120.0 . . ?
H8CA N8C H8CB 120.0 . . ?
C3C N8C H8CA 120.0 . . ?
C3C N8C H8CB 120.0 . . ?
N2C C1C N3C 140.7(6) . . ?
N2C C1C N5C 114.1(5) . . ?
N5C C1C N3C 105.3(5) . . ?
N4C C2C N3C 114.7(5) . . ?
N4C C2C N7C 126.6(5) . . ?
N7C C2C N3C 118.7(6) . . ?
N5C C3C N1C 104.0(5) . . ?
N8C C3C N1C 128.2(5) . . ?
N8C C3C N5C 127.8(5) . . ?
N2E N1E H1E 123.1 . . ?
C3E N1E H1E 123.1 . . ?
C3E N1E N2E 113.9(5) . . ?
C1E N2E N1E 100.5(5) . . ?
C1E N3E N6E 128.1(5) . . ?
C1E N3E C2E 106.7(5) . . ?
C2E N3E N6E 125.1(5) . . ?
C2E N4E N5E 102.0(4) . . ?
C1E N5E N4E 113.6(5) . . ?
C1E N5E C3E 107.0(5) . . ?
C3E N5E N4E 139.4(5) . . ?
N3E N6E H6EA 109.4 . . ?
N3E N6E H6EB 109.7 . . ?
H6EA N6E H6EB 109.2 . . ?
H7EA N7E H7EB 120.0 . . ?
C2E N7E H7EA 120.0 . . ?
C2E N7E H7EB 120.0 . . ?
H8EA N8E H8EB 120.0 . . ?
C3E N8E H8EA 120.0 . . ?
C3E N8E H8EB 120.0 . . ?
N2E C1E N3E 139.9(6) . . ?
N2E C1E N5E 115.2(5) . . ?
N5E C1E N3E 104.9(5) . . ?
N4E C2E N3E 112.7(5) . . ?
N4E C2E N7E 126.6(5) . . ?
N7E C2E N3E 120.6(5) . . ?
N1E C3E N5E 103.5(5) . . ?
N8E C3E N1E 127.6(5) . . ?
N8E C3E N5E 128.9(5) . . ?
N2B N1B H1B 123.3 . . ?
C3B N1B H1B 123.3 . . ?
C3B N1B N2B 113.4(5) . . ?
C1B N2B N1B 100.7(5) . . ?
C1B N3B N6B 129.1(5) . . ?
C1B N3B C2B 106.0(5) . . ?
C2B N3B N6B 124.6(5) . . ?
C2B N4B N5B 101.7(5) . . ?
C1B N5B N4B 112.9(5) . . ?
C3B N5B N4B 138.7(5) . . ?
C3B N5B C1B 108.4(5) . . ?
N3B N6B H6BA 110.1 . . ?
N3B N6B H6BB 110.1 . . ?
H6BA N6B H6BB 108.9 . . ?
H7BA N7B H7BB 120.0 . . ?
C2B N7B H7BA 120.0 . . ?
C2B N7B H7BB 120.0 . . ?
H8BA N8B H8BB 120.0 . . ?
C3B N8B H8BA 120.0 . . ?
C3B N8B H8BB 120.0 . . ?
N2B C1B N3B 140.9(6) . . ?
N2B C1B N5B 113.6(5) . . ?
N5B C1B N3B 105.4(5) . . ?
N4B C2B N3B 113.9(5) . . ?
N4B C2B N7B 125.4(5) . . ?
N7B C2B N3B 120.5(5) . . ?
N5B C3B N1B 103.8(5) . . ?
N8B C3B N1B 128.9(5) . . ?
N8B C3B N5B 127.2(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1D H1D O2 0.88 2.35 3.100(7) 143.9 3_485 yes
N6D H6DA O9 0.88 2.45 2.882(7) 110.8 . yes
N7D H7DA O2A 0.88 2.01 2.885(7) 171.0 4_644 yes
N7D H7DB O4 0.88 2.22 2.944(7) 139.5 1_545 yes
N8D H8DA O3 0.88 1.95 2.807(7) 163.5 3_485 yes
N8D H8DB N4E 0.88 2.12 2.917(7) 151.0 3_475 yes
N1C H1C O5A 0.88 2.36 2.948(6) 124.1 1_565 yes
N1C H1C O9A 0.88 2.38 3.014(7) 129.2 1_565 yes
N6C H6CB O6A 0.89 2.13 2.998(7) 164.9 3_475 yes
N7C H7CA O6 0.88 1.95 2.830(7) 177.0 1_545 yes
N7C H7CA O7 0.88 2.49 3.092(7) 125.8 1_545 yes
N7C H7CB O7A 0.88 2.18 3.030(7) 162.9 3_465 yes
N8C H8CA N4B 0.88 2.10 2.923(7) 156.2 . yes
N8C H8CB O9A 0.88 2.03 2.800(7) 145.4 1_565 yes
N1E H1E N2A 0.88 1.92 2.760(7) 159.6 2_784 yes
N6E H6EB O4A 0.88 2.22 3.006(7) 147.9 4_664 yes
N7E H7EB O3A 0.88 2.37 2.959(7) 124.6 4_654 yes
N8E H8EA O2A 0.88 2.26 3.015(7) 143.8 2_784 yes
N8E H8EA N1A 0.88 2.27 3.038(7) 145.2 2_784 yes
N8E H8EB N4D 0.88 2.21 3.031(7) 156.1 3_575 yes
N1B H1B N1 0.88 1.99 2.829(7) 158.0 1_545 yes
N6B H6BA O8 0.89 2.25 2.971(7) 138.4 3_565 yes
N6B H6BB N2D 0.89 2.20 3.011(6) 151.9 3_575 yes
N7B H7BB O7 0.88 2.37 2.917(7) 120.2 3_575 yes
N8B H8BB O6 0.88 2.08 2.800(7) 139.0 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 N3 154.8(5) . . . . ?
O1 C1 C3 N4 -33.3(8) . . . . ?
O1 C2 C4 N5 -110.8(6) . . . . ?
O1 C2 C4 N6 58.5(8) . . . . ?
O2 N3 C3 N4 174.4(6) . . . . ?
O2 N3 C3 C1 -13.8(9) . . . . ?
O3 N3 C3 N4 -6.8(9) . . . . ?
O3 N3 C3 C1 165.0(6) . . . . ?
O4 N4 C3 N3 -23.3(9) . . . . ?
O4 N4 C3 C1 164.9(5) . . . . ?
O5 N4 C3 N3 156.5(6) . . . . ?
O5 N4 C3 C1 -15.3(9) . . . . ?
O6 N5 C4 N6 -178.0(5) . . . . ?
O6 N5 C4 C2 -8.8(8) . . . . ?
O7 N5 C4 N6 2.4(9) . . . . ?
O7 N5 C4 C2 171.6(5) . . . . ?
O8 N6 C4 N5 -1.6(9) . . . . ?
O8 N6 C4 C2 -170.5(5) . . . . ?
O9 N6 C4 N5 179.6(5) . . . . ?
O9 N6 C4 C2 10.7(8) . . . . ?
N1 N2 C2 O1 1.0(6) . . . . ?
N1 N2 C2 C4 -170.6(6) . . . . ?
N1 C1 C3 N3 -21.3(9) . . . . ?
N1 C1 C3 N4 150.6(6) . . . . ?
N2 N1 C1 O1 0.0(7) . . . . ?
N2 N1 C1 C3 176.3(6) . . . . ?
N2 C2 C4 N5 60.2(9) . . . . ?
N2 C2 C4 N6 -130.4(7) . . . . ?
C1 O1 C2 N2 -1.0(6) . . . . ?
C1 O1 C2 C4 171.5(5) . . . . ?
C1 N1 N2 C2 -0.6(6) . . . . ?
C2 O1 C1 N1 0.6(6) . . . . ?
C2 O1 C1 C3 -176.1(5) . . . . ?
O1A C1A C3A N3A 154.0(5) . . . . ?
O1A C1A C3A N4A -25.1(9) . . . . ?
O1A C2A C4A N5A -163.1(5) . . . . ?
O1A C2A C4A N6A 24.7(8) . . . . ?
O2A N3A C3A N4A 167.5(5) . . . . ?
O2A N3A C3A C1A -11.6(8) . . . . ?
O3A N3A C3A N4A -13.4(9) . . . . ?
O3A N3A C3A C1A 167.5(5) . . . . ?
O4A N4A C3A N3A -14.7(8) . . . . ?
O4A N4A C3A C1A 164.4(6) . . . . ?
O5A N4A C3A N3A 166.4(5) . . . . ?
O5A N4A C3A C1A -14.5(8) . . . . ?
O6A N5A C4A N6A -163.9(5) . . . . ?
O6A N5A C4A C2A 23.8(8) . . . . ?
O7A N5A C4A N6A 18.9(8) . . . . ?
O7A N5A C4A C2A -153.4(5) . . . . ?
O8A N6A C4A N5A 21.4(8) . . . . ?
O8A N6A C4A C2A -166.5(6) . . . . ?
O9A N6A C4A N5A -160.0(5) . . . . ?
O9A N6A C4A C2A 12.1(8) . . . . ?
N1A N2A C2A O1A -1.0(7) . . . . ?
N1A N2A C2A C4A -178.7(6) . . . . ?
N1A C1A C3A N3A -21.2(9) . . . . ?
N1A C1A C3A N4A 159.7(6) . . . . ?
N2A N1A C1A O1A 0.6(7) . . . . ?
N2A N1A C1A C3A 176.2(6) . . . . ?
N2A C2A C4A N5A 14.4(9) . . . . ?
N2A C2A C4A N6A -157.9(6) . . . . ?
C1A O1A C2A N2A 1.3(6) . . . . ?
C1A O1A C2A C4A 179.2(5) . . . . ?
C1A N1A N2A C2A 0.2(7) . . . . ?
C2A O1A C1A N1A -1.2(6) . . . . ?
C2A O1A C1A C3A -177.1(5) . . . . ?
N1D N2D C1D N3D 175.2(8) . . . . ?
N1D N2D C1D N5D -1.0(7) . . . . ?
N2D N1D C3D N5D 0.8(7) . . . . ?
N2D N1D C3D N8D -179.2(6) . . . . ?
N4D N5D C1D N2D 178.7(5) . . . . ?
N4D N5D C1D N3D 1.2(7) . . . . ?
N4D N5D C3D N1D -177.4(6) . . . . ?
N4D N5D C3D N8D 2.6(12) . . . . ?
N5D N4D C2D N3D 0.8(6) . . . . ?
N5D N4D C2D N7D 178.3(6) . . . . ?
N6D N3D C1D N2D 6.5(13) . . . . ?
N6D N3D C1D N5D -177.1(6) . . . . ?
N6D N3D C2D N4D 176.6(5) . . . . ?
N6D N3D C2D N7D -1.1(9) . . . . ?
C1D N3D C2D N4D -0.1(7) . . . . ?
C1D N3D C2D N7D -177.8(5) . . . . ?
C1D N5D C3D N1D -1.4(6) . . . . ?
C1D N5D C3D N8D 178.6(6) . . . . ?
C2D N3D C1D N2D -177.1(8) . . . . ?
C2D N3D C1D N5D -0.7(6) . . . . ?
C2D N4D N5D C1D -1.3(6) . . . . ?
C2D N4D N5D C3D 174.7(7) . . . . ?
C3D N1D N2D C1D 0.1(7) . . . . ?
C3D N5D C1D N2D 1.6(7) . . . . ?
C3D N5D C1D N3D -175.9(5) . . . . ?
N1C N2C C1C N3C 178.2(7) . . . . ?
N1C N2C C1C N5C -0.7(6) . . . . ?
N2C N1C C3C N5C -1.8(7) . . . . ?
N2C N1C C3C N8C 179.5(6) . . . . ?
N4C N5C C1C N2C 178.9(5) . . . . ?
N4C N5C C1C N3C -0.4(6) . . . . ?
N4C N5C C3C N1C -177.7(6) . . . . ?
N4C N5C C3C N8C 1.1(12) . . . . ?
N5C N4C C2C N3C -0.5(6) . . . . ?
N5C N4C C2C N7C -179.4(6) . . . . ?
N6C N3C C1C N2C -4.9(12) . . . . ?
N6C N3C C1C N5C 174.0(5) . . . . ?
N6C N3C C2C N4C -174.2(5) . . . . ?
N6C N3C C2C N7C 4.8(9) . . . . ?
C1C N3C C2C N4C 0.3(7) . . . . ?
C1C N3C C2C N7C 179.3(5) . . . . ?
C1C N5C C3C N1C 1.2(6) . . . . ?
C1C N5C C3C N8C 180.0(6) . . . . ?
C2C N3C C1C N2C -178.9(8) . . . . ?
C2C N3C C1C N5C 0.0(6) . . . . ?
C2C N4C N5C C1C 0.5(6) . . . . ?
C2C N4C N5C C3C 179.4(7) . . . . ?
C3C N1C N2C C1C 1.5(6) . . . . ?
C3C N5C C1C N2C -0.3(7) . . . . ?
C3C N5C C1C N3C -179.6(5) . . . . ?
N1E N2E C1E N3E 177.8(7) . . . . ?
N1E N2E C1E N5E -0.8(7) . . . . ?
N2E N1E C3E N5E 0.6(7) . . . . ?
N2E N1E C3E N8E -179.2(6) . . . . ?
N4E N5E C1E N2E 179.0(5) . . . . ?
N4E N5E C1E N3E -0.1(6) . . . . ?
N4E N5E C3E N1E -177.8(6) . . . . ?
N4E N5E C3E N8E 2.0(12) . . . . ?
N5E N4E C2E N3E -1.0(6) . . . . ?
N5E N4E C2E N7E 177.3(5) . . . . ?
N6E N3E C1E N2E 4.2(12) . . . . ?
N6E N3E C1E N5E -177.2(5) . . . . ?
N6E N3E C2E N4E 177.8(5) . . . . ?
N6E N3E C2E N7E -0.7(9) . . . . ?
C1E N3E C2E N4E 1.0(7) . . . . ?
C1E N3E C2E N7E -177.4(5) . . . . ?
C1E N5E C3E N1E -1.0(6) . . . . ?
C1E N5E C3E N8E 178.8(6) . . . . ?
C2E N3E C1E N2E -179.2(7) . . . . ?
C2E N3E C1E N5E -0.5(6) . . . . ?
C2E N4E N5E C1E 0.7(6) . . . . ?
C2E N4E N5E C3E 177.3(7) . . . . ?
C3E N1E N2E C1E 0.1(7) . . . . ?
C3E N5E C1E N2E 1.2(7) . . . . ?
C3E N5E C1E N3E -177.8(5) . . . . ?
N1B N2B C1B N3B 178.8(8) . . . . ?
N1B N2B C1B N5B -1.0(6) . . . . ?
N2B N1B C3B N5B -2.5(6) . . . . ?
N2B N1B C3B N8B 180.0(6) . . . . ?
N4B N5B C1B N2B -179.1(5) . . . . ?
N4B N5B C1B N3B 1.1(7) . . . . ?
N4B N5B C3B N1B 179.8(6) . . . . ?
N4B N5B C3B N8B -2.7(11) . . . . ?
N5B N4B C2B N3B -0.5(7) . . . . ?
N5B N4B C2B N7B 176.1(5) . . . . ?
N6B N3B C1B N2B -7.2(12) . . . . ?
N6B N3B C1B N5B 172.5(5) . . . . ?
N6B N3B C2B N4B -173.0(5) . . . . ?
N6B N3B C2B N7B 10.2(9) . . . . ?
C1B N3B C2B N4B 1.2(7) . . . . ?
C1B N3B C2B N7B -175.6(5) . . . . ?
C1B N5B C3B N1B 1.8(6) . . . . ?
C1B N5B C3B N8B 179.3(6) . . . . ?
C2B N3B C1B N2B 178.9(8) . . . . ?
C2B N3B C1B N5B -1.3(6) . . . . ?
C2B N4B N5B C1B -0.4(6) . . . . ?
C2B N4B N5B C3B -178.3(7) . . . . ?
C3B N1B N2B C1B 2.2(6) . . . . ?
C3B N5B C1B N2B -0.5(7) . . . . ?
C3B N5B C1B N3B 179.7(5) . . . . ?

_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 'JS1000  Thin Green Needles'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.794
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4(5)
2 0.6(5)

####################################################################### 
# 
# 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_js424b
_database_code_depnum_ccdc_archive 'CCDC 2350679'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_audit_creation_date             2024-04-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 N6 O9, 2(C3 H7 N8), H2 O'
_chemical_formula_sum            'C10 H16 N22 O10'
_chemical_formula_weight         604.45
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H14N22O9
_chemical_oxdiff_usercomment     JS1000
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.30682(19)
_cell_length_b                   52.5690(11)
_cell_length_c                   5.13161(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2240.88(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5456
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.3880
_cell_measurement_theta_min      3.3680
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.96a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 -3 0.0617
-1 4 3 0.0617
0 -1 0 0.0230
5 0 0 0.0448
-1 0 0 0.0448
0 1 0 0.0043

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.027
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
0.9944 -4.0140 -3.0014 -0.5548 0.6832 0.2920
-1.0063 4.0721 3.0018 0.5542 -0.6836 -0.2947
0.0006 -0.9994 0.0003 0.0208 0.0167 0.0121
5.3971 -0.2279 0.0064 -0.2530 -0.3263 0.9117
-1.0005 -0.0037 0.0003 0.0481 0.0609 -0.1685
-0.0006 0.9994 -0.0003 -0.0208 -0.0167 -0.0121

_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  0.0989
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            40579
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.271
_diffrn_reflns_theta_min         3.363
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  22.00   0.50    0.05    --   46.31 -19.00   0.00   56
  2  ω     -1.00  28.00   0.50    0.05    --   46.31 -19.00 -30.00   58
  3  ω    -29.00  15.00   0.50    0.05    --   46.31 -19.00-150.00   88
  4  ω     42.00  94.00   0.50    0.05    --   46.31-125.00 -90.00  104
  5  ω     66.00 106.00   0.50    0.08    --  115.25-125.00-180.00   80
  6  ω     83.00 108.00   0.50    0.08    --  115.25-125.00-120.00   50
  7  ω     46.00  95.00   0.50    0.08    --  115.25-125.00 -60.00   98
  8  ω     73.00 104.00   0.50    0.08    --  115.25 -94.00-150.00   62
  9  ω     46.00  72.00   0.50    0.08    --  115.25-125.00  60.00   52
 10  ω     83.00 108.00   0.50    0.08    --  115.25-125.00 150.00   50
 11  ω     83.00 108.00   0.50    0.08    --  115.25-125.00  90.00   50
 12  ω     78.00 104.00   0.50    0.08    --  115.25 -94.00  30.00   52
 13  ω     45.00  79.00   0.50    0.08    --  115.25 -94.00 -30.00   68
 14  ω     44.00 104.00   0.50    0.08    --  115.25 -94.00 -60.00  120
 15  ω     60.00 103.00   0.50    0.08    --  115.25 -94.00-120.00   86
 16  ω     67.00 104.00   0.50    0.08    --  115.25 -94.00-180.00   74
 17  ω     62.00 104.00   0.50    0.08    --  115.25 -94.00   0.00   84
 18  ω     44.00  77.00   0.50    0.08    --  115.25 -94.00  60.00   66
 19  ω     45.00  71.00   0.50    0.08    --  115.25 -94.00  90.00   52
 20  ω     43.00  75.00   0.50    0.08    --  115.25 -94.00 120.00   64
 21  ω     44.00  81.00   0.50    0.08    --  115.25 -86.00 125.38   74
 22  ω     79.00 104.00   0.50    0.08    --  115.25 -94.00 120.00   50
 23  ω     61.00  94.00   0.50    0.08    --  115.25 -86.00 -83.60   66
 24  ω     70.00 111.00   0.50    0.08    --  115.25 -86.00-125.54   82
 25  ω    118.00 144.00   0.50    0.08    --  115.25 -86.00-125.54   52
 26  ω     91.00 116.00   0.50    0.08    --  115.25 -86.00 -69.81   50
 27  ω    101.00 127.00   0.50    0.08    --  115.25 -86.00 -83.60   52
 28  ω     96.00 123.00   0.50    0.08    --  115.25 -84.00  36.03   54
 29  ω    111.00 144.00   0.50    0.08    --  115.25 -85.00  99.00   66
 30  ω    108.00 135.00   0.50    0.08    --  115.25 -86.00 125.38   54
 31  ω     43.00  69.00   0.50    0.08    --  115.25 -85.00  99.00   52
 32  ω     45.00  70.00   0.50    0.08    --  115.25 -84.00  36.03   50
 33  ω     43.00  68.00   0.50    0.08    --  115.25 -81.00 -80.79   50
 34  ω     86.00 142.00   0.50    0.08    --  115.25 -81.00 -75.75  112
 35  ω    117.00 142.00   0.50    0.08    --  115.25 -82.00-167.85   50
 36  ω     43.00  73.00   0.50    0.08    --  115.25 -82.00-167.85   60
 37  ω     43.00  68.00   0.50    0.08    --  115.25 -61.00-120.00   50
 38  ω     54.00  79.00   0.50    0.08    --  115.25 -77.00-150.00   50
 39  ω     53.00  79.00   0.50    0.08    --  115.25 -77.00 -30.00   52
 40  ω     43.00  68.00   0.50    0.08    --  115.25 -61.00 -60.00   50
 41  ω     43.00  68.00   0.50    0.08    --  115.25 -61.00 -30.00   50
 42  ω     44.00  93.00   0.50    0.08    --  115.25 -77.00   0.00   98
 43  ω     75.00 100.00   0.50    0.08    --  115.25 -77.00  30.00   50
 44  ω     44.00  77.00   0.50    0.08    --  115.25 -77.00  60.00   66
 45  ω     43.00  68.00   0.50    0.08    --  115.25 -61.00  60.00   50
 46  ω    150.00 175.00   0.50    0.08    --  115.25  15.00  60.00   50
 47  ω    122.00 171.00   0.50    0.08    --  115.25  77.00  90.00   98
 48  ω    144.00 177.00   0.50    0.08    --  115.25  77.00   0.00   66
 49  ω    115.00 178.00   0.50    0.08    --  115.25  77.00 -30.00  126
 50  ω    112.00 137.00   0.50    0.08    --  115.25  77.00  30.00   50
 51  ω    141.00 167.00   0.50    0.08    --  115.25  61.00  60.00   52
 52  ω    153.00 178.00   0.50    0.08    --  115.25  77.00 -60.00   50
 53  ω    124.00 149.00   0.50    0.08    --  115.25  77.00-120.00   50
 54  ω    107.00 172.00   0.50    0.08    --  115.25  61.00-150.00  130
 55  ω    151.00 176.00   0.50    0.08    --  115.25  77.00-180.00   50
 56  ω    121.00 149.00   0.50    0.08    --  115.25  61.00-180.00   56
 57  ω    110.00 138.00   0.50    0.08    --  115.25  45.00  30.00   56
 58  ω    142.00 167.00   0.50    0.08    --  115.25  45.00  30.00   50
 59  ω    102.00 162.00   0.50    0.08    --  115.25  45.00  90.00  120
 60  ω    108.00 153.00   0.50    0.08    --  115.25  61.00 150.00   90
 61  ω     99.00 135.00   0.50    0.08    --  115.25  45.00 150.00   72
 62  ω    115.00 174.00   0.50    0.08    --  115.25  30.00 -30.00  118
 63  ω    112.00 138.00   0.50    0.08    --  115.25  30.00  30.00   52
 64  ω     95.00 120.00   0.50    0.08    --  115.25  15.00  30.00   50
 65  ω    100.00 139.00   0.50    0.08    --  115.25  15.00  60.00   78
 66  ω    115.00 166.00   0.50    0.08    --  115.25  15.00 150.00  102
 67  ω    106.00 132.00   0.50    0.08    --  115.25  45.00 -90.00   52
 68  ω    108.00 152.00   0.50    0.08    --  115.25  30.00 -90.00   88
 69  ω     97.00 129.00   0.50    0.08    --  115.25  15.00-150.00   64
 70  ω    122.00 176.00   0.50    0.08    --  115.25  45.00-180.00  108
 71  ω     99.00 143.00   0.50    0.08    --  115.25 125.00 -90.00   88
 72  ω    126.00 152.00   0.50    0.08    --  115.25 125.00 -30.00   52
 73  ω    136.00 162.00   0.50    0.08    --  115.25 125.00 -60.00   52
 74  ω    129.00 154.00   0.50    0.08    --  115.25 125.00   0.00   50
 75  ω     98.00 133.00   0.50    0.08    --  115.25 125.00  60.00   70
 76  ω    -24.00  15.00   0.50    0.05    --  -46.31  19.00-120.00   78
 77  ω    -42.00  16.00   0.50    0.05    --  -46.31  37.00   0.00  116
 78  ω    -68.00 -29.00   0.50    0.08    --  -93.75  61.00  60.00   78
 79  ω    -44.00  27.00   0.50    0.05    --  -46.31  37.00 120.00  142
 80  ω   -114.00 -45.00   0.50    0.05    --  -46.31 -37.00 -30.00  138
 81  ω   -131.00-106.00   0.50    0.08    --  -93.75 -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      -0.0479856000
_diffrn_orient_matrix_UB_12      -0.0207951000
_diffrn_orient_matrix_UB_13      0.1967519000
_diffrn_orient_matrix_UB_21      -0.0609066000
_diffrn_orient_matrix_UB_22      -0.0168113000
_diffrn_orient_matrix_UB_23      -0.2253315000
_diffrn_orient_matrix_UB_31      0.1684446000
_diffrn_orient_matrix_UB_32      -0.0119979000
_diffrn_orient_matrix_UB_33      -0.0254268000
_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         0.789
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4465
_reflns_number_total             4905
_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 1.171.43.96a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1797 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.077
_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)+(0.0464P)²+1.2193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1115
_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 -0.1332(3) 0.62126(4) 0.0694(5) 0.0214(5) Uani 1 1 d . . . . .
O2 O -0.2499(3) 0.54758(5) 0.0818(6) 0.0259(6) Uani 1 1 d . . . . .
O3 O -0.0666(3) 0.53633(5) -0.1989(6) 0.0275(6) Uani 1 1 d . . . . .
O4 O 0.0908(3) 0.57288(5) -0.4125(6) 0.0314(6) Uani 1 1 d . . . . .
O5 O 0.1210(3) 0.60554(5) -0.1604(6) 0.0254(6) Uani 1 1 d . . . . .
O6 O -0.3881(4) 0.66291(6) -0.0327(7) 0.0362(7) Uani 1 1 d . . . . .
O7 O -0.2929(4) 0.69822(5) 0.1270(7) 0.0345(7) Uani 1 1 d . . . . .
O8 O -0.1048(4) 0.69281(5) 0.5288(7) 0.0387(8) Uani 1 1 d . . . . .
O9 O -0.0235(4) 0.65393(5) 0.5976(7) 0.0367(7) Uani 1 1 d . . . . .
N1 N -0.2344(4) 0.59196(6) 0.3282(7) 0.0247(6) Uani 1 1 d . . . . .
N2 N -0.2779(4) 0.61587(6) 0.4232(7) 0.0248(6) Uani 1 1 d . . . . .
N3 N -0.1338(3) 0.55287(6) -0.0632(7) 0.0225(6) Uani 1 1 d . . . . .
N4 N 0.0491(3) 0.58553(5) -0.2211(7) 0.0222(6) Uani 1 1 d . . . . .
N5 N -0.3010(4) 0.67463(6) 0.1243(7) 0.0262(6) Uani 1 1 d . . . . .
N6 N -0.1113(4) 0.66947(6) 0.4798(7) 0.0276(7) Uani 1 1 d . . . . .
C1 C -0.1490(4) 0.59597(6) 0.1182(8) 0.0207(7) Uani 1 1 d . . . . .
C2 C -0.2158(4) 0.63230(6) 0.2682(8) 0.0215(7) Uani 1 1 d . . . . .
C3 C -0.0804(4) 0.57811(6) -0.0614(8) 0.0205(7) Uani 1 1 d . . . . .
C4 C -0.2126(4) 0.65968(7) 0.2956(8) 0.0222(7) Uani 1 1 d . . . . .
N1A N 0.5519(3) 0.56364(5) -0.3896(7) 0.0208(6) Uani 1 1 d . . . . .
H1A H 0.632(7) 0.5687(10) -0.502(12) 0.042(15) Uiso 1 1 d . . . . .
N2A N 0.5007(3) 0.53821(5) -0.3912(7) 0.0208(6) Uani 1 1 d . . . . .
N3A N 0.3041(3) 0.52206(5) -0.0583(6) 0.0196(6) Uani 1 1 d . . . . .
N4A N 0.2844(3) 0.56061(5) 0.1409(6) 0.0206(6) Uani 1 1 d . . . . .
N5A N 0.3915(3) 0.56068(5) -0.0681(6) 0.0190(6) Uani 1 1 d . . . . .
N6A N 0.2498(4) 0.49786(6) -0.1265(7) 0.0229(6) Uani 1 1 d . . . . .
H6AA H 0.326(6) 0.4857(11) -0.073(12) 0.038(14) Uiso 1 1 d . . . . .
H6AB H 0.228(6) 0.4982(9) -0.302(12) 0.028(13) Uiso 1 1 d . . . . .
N7A N 0.1340(4) 0.52570(6) 0.3086(7) 0.0243(6) Uani 1 1 d . . . . .
H7AA H 0.078(6) 0.5357(9) 0.426(12) 0.032(12) Uiso 1 1 d . . . . .
H7AB H 0.099(6) 0.5111(11) 0.261(12) 0.035(13) Uiso 1 1 d . . . . .
N8A N 0.5083(4) 0.60192(6) -0.1408(7) 0.0235(6) Uani 1 1 d . . . . .
H8AA H 0.573(6) 0.6114(9) -0.260(10) 0.024(11) Uiso 1 1 d . . . . .
H8AB H 0.465(7) 0.6079(11) -0.009(12) 0.040(16) Uiso 1 1 d . . . . .
C1A C 0.4041(4) 0.53798(6) -0.1926(8) 0.0202(7) Uani 1 1 d . . . . .
C2A C 0.2345(4) 0.53661(6) 0.1385(7) 0.0211(7) Uani 1 1 d . . . . .
C3A C 0.4857(4) 0.57732(6) -0.1972(7) 0.0202(6) Uani 1 1 d . . . . .
N1B N 0.1075(4) 0.70011(6) -0.0585(7) 0.0271(6) Uani 1 1 d . . . . .
H1B H 0.022(8) 0.6973(12) -0.204(16) 0.060(18) Uiso 1 1 d . . . . .
N2B N 0.1397(4) 0.72514(6) 0.0268(7) 0.0280(7) Uani 1 1 d . . . . .
N3B N 0.3331(4) 0.73248(6) 0.3968(7) 0.0270(7) Uani 1 1 d . . . . .
N4B N 0.3827(4) 0.69036(6) 0.4531(8) 0.0282(7) Uani 1 1 d . . . . .
N5B N 0.2737(4) 0.69524(6) 0.2511(7) 0.0258(7) Uani 1 1 d . . . . .
N6B N 0.3567(4) 0.75817(6) 0.4472(8) 0.0312(7) Uani 1 1 d . . . . .
H6BA H 0.257(8) 0.7636(11) 0.498(13) 0.045(16) Uiso 1 1 d . . . . .
H6BB H 0.397(9) 0.7676(14) 0.293(19) 0.08(2) Uiso 1 1 d . . . . .
N7B N 0.5200(5) 0.72038(7) 0.7179(8) 0.0348(8) Uani 1 1 d . . . . .
H7BA H 0.516(5) 0.7393(8) 0.744(11) 0.025(11) Uiso 1 1 d . . . . .
H7BB H 0.566(6) 0.7080(10) 0.817(13) 0.039(14) Uiso 1 1 d . . . . .
N8B N 0.1835(4) 0.65719(6) 0.0438(8) 0.0308(7) Uani 1 1 d . . . . .
H8BA H 0.119(6) 0.6500(10) -0.076(12) 0.032(13) Uiso 1 1 d . . . . .
H8BB H 0.238(8) 0.6475(12) 0.144(15) 0.057(19) Uiso 1 1 d . . . . .
C1B C 0.2423(5) 0.72010(7) 0.2166(9) 0.0262(8) Uani 1 1 d . . . . .
C2B C 0.4163(5) 0.71368(7) 0.5330(8) 0.0278(8) Uani 1 1 d . . . . .
C3B C 0.1878(4) 0.68205(7) 0.0753(8) 0.0266(8) Uani 1 1 d . . . . .
O1W O 0.3103(3) 0.61467(6) 0.3300(6) 0.0303(6) Uani 1 1 d . . . . .
H1WA H 0.270(9) 0.5994(15) 0.299(19) 0.07(2) Uiso 1 1 d . . . . .
H1WB H 0.281(15) 0.624(3) 0.47(3) 0.18(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 C1 1.359(4) . ?
O1 C2 1.360(5) . ?
O2 N3 1.249(4) . ?
O3 N3 1.246(4) . ?
O4 N4 1.236(4) . ?
O5 N4 1.249(4) . ?
O6 N5 1.246(5) . ?
O7 N5 1.242(4) . ?
O8 N6 1.254(4) . ?
O9 N6 1.251(4) . ?
N1 N2 1.396(4) . ?
N1 C1 1.307(5) . ?
N2 C2 1.283(5) . ?
N3 C3 1.399(4) . ?
N4 C3 1.407(5) . ?
N5 C4 1.389(5) . ?
N6 C4 1.366(5) . ?
C1 C3 1.434(5) . ?
C2 C4 1.446(5) . ?
N1A H1A 0.92(6) . ?
N1A N2A 1.403(4) . ?
N1A C3A 1.339(5) . ?
N2A C1A 1.297(5) . ?
N3A N6A 1.394(4) . ?
N3A C1A 1.366(4) . ?
N3A C2A 1.393(5) . ?
N4A N5A 1.393(4) . ?
N4A C2A 1.328(4) . ?
N5A C1A 1.358(5) . ?
N5A C3A 1.348(4) . ?
N6A H6AA 0.94(6) . ?
N6A H6AB 0.92(6) . ?
N7A H7AA 0.92(6) . ?
N7A H7AB 0.86(6) . ?
N7A C2A 1.337(5) . ?
N8A H8AA 0.96(5) . ?
N8A H8AB 0.83(6) . ?
N8A C3A 1.338(4) . ?
N1B H1B 1.04(7) . ?
N1B N2B 1.412(5) . ?
N1B C3B 1.348(5) . ?
N2B C1B 1.321(5) . ?
N3B N6B 1.389(4) . ?
N3B C1B 1.360(5) . ?
N3B C2B 1.394(5) . ?
N4B N5B 1.400(5) . ?
N4B C2B 1.322(5) . ?
N5B C1B 1.345(5) . ?
N5B C3B 1.343(5) . ?
N6B H6BA 0.91(6) . ?
N6B H6BB 0.99(9) . ?
N7B H7BA 1.00(4) . ?
N7B H7BB 0.91(6) . ?
N7B C2B 1.329(6) . ?
N8B H8BA 0.90(6) . ?
N8B H8BB 0.85(7) . ?
N8B C3B 1.317(5) . ?
O1W H1WA 0.88(8) . ?
O1W H1WB 0.90(15) . ?

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
C2 O1 C1 103.3(3) . . ?
C1 N1 N2 106.5(3) . . ?
C2 N2 N1 106.6(3) . . ?
O2 N3 C3 116.9(3) . . ?
O3 N3 O2 121.6(3) . . ?
O3 N3 C3 121.5(3) . . ?
O4 N4 O5 121.1(3) . . ?
O4 N4 C3 121.9(3) . . ?
O5 N4 C3 117.0(3) . . ?
O6 N5 C4 115.9(3) . . ?
O7 N5 O6 122.2(3) . . ?
O7 N5 C4 122.0(3) . . ?
O8 N6 C4 122.3(3) . . ?
O9 N6 O8 121.1(3) . . ?
O9 N6 C4 116.6(3) . . ?
O1 C1 C3 118.9(3) . . ?
N1 C1 O1 111.2(3) . . ?
N1 C1 C3 129.8(3) . . ?
O1 C2 C4 119.3(3) . . ?
N2 C2 O1 112.4(3) . . ?
N2 C2 C4 128.1(4) . . ?
N3 C3 N4 120.1(3) . . ?
N3 C3 C1 119.9(3) . . ?
N4 C3 C1 119.8(3) . . ?
N5 C4 C2 119.4(3) . . ?
N6 C4 N5 123.4(3) . . ?
N6 C4 C2 117.0(3) . . ?
N2A N1A H1A 119(4) . . ?
C3A N1A H1A 127(4) . . ?
C3A N1A N2A 113.0(3) . . ?
C1A N2A N1A 101.1(3) . . ?
C1A N3A N6A 129.0(3) . . ?
C1A N3A C2A 106.4(3) . . ?
C2A N3A N6A 123.3(3) . . ?
C2A N4A N5A 101.2(3) . . ?
C1A N5A N4A 114.1(3) . . ?
C3A N5A N4A 138.7(3) . . ?
C3A N5A C1A 107.1(3) . . ?
N3A N6A H6AA 109(3) . . ?
N3A N6A H6AB 107(3) . . ?
H6AA N6A H6AB 116(5) . . ?
H7AA N7A H7AB 122(5) . . ?
C2A N7A H7AA 120(3) . . ?
C2A N7A H7AB 114(4) . . ?
H8AA N8A H8AB 125(5) . . ?
C3A N8A H8AA 116(3) . . ?
C3A N8A H8AB 119(4) . . ?
N2A C1A N3A 141.1(3) . . ?
N2A C1A N5A 114.1(3) . . ?
N5A C1A N3A 104.7(3) . . ?
N4A C2A N3A 113.5(3) . . ?
N4A C2A N7A 126.6(3) . . ?
N7A C2A N3A 119.8(3) . . ?
N1A C3A N5A 104.6(3) . . ?
N8A C3A N1A 128.3(3) . . ?
N8A C3A N5A 127.0(3) . . ?
N2B N1B H1B 119(3) . . ?
C3B N1B H1B 127(3) . . ?
C3B N1B N2B 113.9(3) . . ?
C1B N2B N1B 99.4(3) . . ?
N6B N3B C2B 121.8(3) . . ?
C1B N3B N6B 132.1(3) . . ?
C1B N3B C2B 106.1(3) . . ?
C2B N4B N5B 101.3(3) . . ?
C1B N5B N4B 113.7(3) . . ?
C3B N5B N4B 138.3(3) . . ?
C3B N5B C1B 108.1(3) . . ?
N3B N6B H6BA 103(4) . . ?
N3B N6B H6BB 113(5) . . ?
H6BA N6B H6BB 112(6) . . ?
H7BA N7B H7BB 130(5) . . ?
C2B N7B H7BA 110(3) . . ?
C2B N7B H7BB 119(4) . . ?
H8BA N8B H8BB 118(6) . . ?
C3B N8B H8BA 121(3) . . ?
C3B N8B H8BB 120(5) . . ?
N2B C1B N3B 139.8(4) . . ?
N2B C1B N5B 114.7(3) . . ?
N5B C1B N3B 105.5(3) . . ?
N4B C2B N3B 113.4(4) . . ?
N4B C2B N7B 127.1(4) . . ?
N7B C2B N3B 119.5(4) . . ?
N5B C3B N1B 104.0(3) . . ?
N8B C3B N1B 128.5(4) . . ?
N8B C3B N5B 127.5(4) . . ?
H1WA O1W H1WB 121(10) . . ?

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
N1A H1A N1 0.92(6) 1.87(6) 2.732(4) 156(5) 1_654 yes
N6A H6AA N2A 0.94(6) 2.13(6) 3.058(4) 170(5) 2_665 yes
N7A H7AA O3 0.92(6) 2.27(6) 3.079(4) 146(4) 1_556 yes
N7A H7AA O4 0.92(6) 2.12(5) 2.886(4) 139(4) 1_556 yes
N8A H8AA N2 0.96(5) 2.06(5) 2.949(5) 155(4) 1_654 yes
N8A H8AB O1W 0.83(6) 2.19(6) 2.999(5) 165(5) . yes
N1B H1B O8 1.04(7) 1.74(7) 2.782(5) 174(6) 1_554 yes
N6B H6BB O7 0.99(9) 2.54(8) 3.082(5) 114(5) 4_565 yes
N7B H7BA N6B 1.00(4) 2.25(5) 2.778(5) 111(4) . yes
N7B H7BB O7 0.91(6) 2.04(6) 2.860(5) 149(5) 1_656 yes
N8B H8BA O5 0.90(6) 2.38(5) 2.956(4) 122(4) . yes
N8B H8BA O9 0.90(6) 2.06(6) 2.869(5) 149(5) 1_554 yes
N8B H8BB O1W 0.85(7) 2.06(7) 2.875(5) 159(6) . yes
O1W H1WA N4A 0.88(8) 2.20(8) 3.011(4) 153(7) . yes
O1W H1WB O5 0.90(15) 2.50(14) 3.089(4) 124(11) 1_556 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 N3 -160.7(3) . . . . ?
O1 C1 C3 N4 24.3(5) . . . . ?
O1 C2 C4 N5 74.2(5) . . . . ?
O1 C2 C4 N6 -100.9(4) . . . . ?
O2 N3 C3 N4 -179.6(3) . . . . ?
O2 N3 C3 C1 5.5(5) . . . . ?
O3 N3 C3 N4 1.9(5) . . . . ?
O3 N3 C3 C1 -173.1(3) . . . . ?
O4 N4 C3 N3 19.8(5) . . . . ?
O4 N4 C3 C1 -165.2(3) . . . . ?
O5 N4 C3 N3 -159.9(3) . . . . ?
O5 N4 C3 C1 15.0(5) . . . . ?
O6 N5 C4 N6 180.0(4) . . . . ?
O6 N5 C4 C2 5.1(5) . . . . ?
O7 N5 C4 N6 0.3(6) . . . . ?
O7 N5 C4 C2 -174.5(4) . . . . ?
O8 N6 C4 N5 8.6(6) . . . . ?
O8 N6 C4 C2 -176.4(4) . . . . ?
O9 N6 C4 N5 -170.9(4) . . . . ?
O9 N6 C4 C2 4.1(5) . . . . ?
N1 N2 C2 O1 0.7(4) . . . . ?
N1 N2 C2 C4 -173.4(4) . . . . ?
N1 C1 C3 N3 16.3(6) . . . . ?
N1 C1 C3 N4 -158.7(4) . . . . ?
N2 N1 C1 O1 0.2(4) . . . . ?
N2 N1 C1 C3 -176.9(4) . . . . ?
N2 C2 C4 N5 -112.0(5) . . . . ?
N2 C2 C4 N6 72.8(5) . . . . ?
C1 O1 C2 N2 -0.6(4) . . . . ?
C1 O1 C2 C4 174.1(3) . . . . ?
C1 N1 N2 C2 -0.5(4) . . . . ?
C2 O1 C1 N1 0.2(4) . . . . ?
C2 O1 C1 C3 177.7(3) . . . . ?
N1A N2A C1A N3A 179.0(5) . . . . ?
N1A N2A C1A N5A -0.4(4) . . . . ?
N2A N1A C3A N5A 0.8(4) . . . . ?
N2A N1A C3A N8A -180.0(3) . . . . ?
N4A N5A C1A N2A 178.4(3) . . . . ?
N4A N5A C1A N3A -1.2(4) . . . . ?
N4A N5A C3A N1A -177.5(4) . . . . ?
N4A N5A C3A N8A 3.3(7) . . . . ?
N5A N4A C2A N3A 0.0(4) . . . . ?
N5A N4A C2A N7A 176.7(4) . . . . ?
N6A N3A C1A N2A -11.4(7) . . . . ?
N6A N3A C1A N5A 168.0(3) . . . . ?
N6A N3A C2A N4A -168.5(3) . . . . ?
N6A N3A C2A N7A 14.5(5) . . . . ?
C1A N3A C2A N4A -0.7(4) . . . . ?
C1A N3A C2A N7A -177.7(3) . . . . ?
C1A N5A C3A N1A -1.0(4) . . . . ?
C1A N5A C3A N8A 179.8(3) . . . . ?
C2A N3A C1A N2A -178.3(5) . . . . ?
C2A N3A C1A N5A 1.1(4) . . . . ?
C2A N4A N5A C1A 0.8(4) . . . . ?
C2A N4A N5A C3A 177.1(4) . . . . ?
C3A N1A N2A C1A -0.3(4) . . . . ?
C3A N5A C1A N2A 0.9(4) . . . . ?
C3A N5A C1A N3A -178.7(3) . . . . ?
N1B N2B C1B N3B 179.1(5) . . . . ?
N1B N2B C1B N5B 0.2(4) . . . . ?
N2B N1B C3B N5B 0.1(4) . . . . ?
N2B N1B C3B N8B 179.8(4) . . . . ?
N4B N5B C1B N2B -180.0(3) . . . . ?
N4B N5B C1B N3B 0.7(5) . . . . ?
N4B N5B C3B N1B 179.8(4) . . . . ?
N4B N5B C3B N8B 0.1(8) . . . . ?
N5B N4B C2B N3B 1.1(4) . . . . ?
N5B N4B C2B N7B -177.2(4) . . . . ?
N6B N3B C1B N2B -2.3(9) . . . . ?
N6B N3B C1B N5B 176.7(4) . . . . ?
N6B N3B C2B N4B -177.9(4) . . . . ?
N6B N3B C2B N7B 0.6(6) . . . . ?
C1B N3B C2B N4B -0.8(5) . . . . ?
C1B N3B C2B N7B 177.7(4) . . . . ?
C1B N5B C3B N1B 0.0(4) . . . . ?
C1B N5B C3B N8B -179.7(4) . . . . ?
C2B N3B C1B N2B -179.0(5) . . . . ?
C2B N3B C1B N5B 0.0(4) . . . . ?
C2B N4B N5B C1B -1.1(4) . . . . ?
C2B N4B N5B C3B 179.1(5) . . . . ?
C3B N1B N2B C1B -0.2(4) . . . . ?
C3B N5B C1B N2B -0.1(5) . . . . ?
C3B N5B C1B N3B -179.4(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'JS1000 Yellow Plates'
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.813
_vrf_PLAT430_js424b              
;
PROBLEM: Short Inter D...A Contact  O4       ..N4A      .       2.87 Ang.  
RESPONSE: We have seen in these small compounds that they will pack with some 
relatively short O---N distances that get flagged by cifcheck routine.
;
