# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2022

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

data_js1121b
_database_code_depnum_ccdc_archive 'CCDC 2160564'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-11-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H2 N14 O6, C H4 O'
_chemical_formula_sum            'C6 H6 N14 O7'
_chemical_formula_weight         386.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C5H2N14O6
_chemical_oxdiff_usercomment     A55
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                   10.8595(2)
_cell_length_b                   12.0844(2)
_cell_length_c                   11.6653(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.799(3)
_cell_angle_gamma                90
_cell_volume                     1400.67(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7314
_cell_measurement_temperature    100.00(12)
_cell_measurement_theta_max      78.4420
_cell_measurement_theta_min      3.6480
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0347
-1 0 -1 0.0195
0 -1 1 0.0201
0 1 -1 0.0401
0 1 1 0.0405
0 -6 -5 0.0335
3 -4 -7 0.0500
-3 4 7 0.0378
6 -1 -6 0.0568
-5 1 7 0.0341
3 4 4 0.0273
-4 -6 -1 0.0110
4 6 -4 0.0498
-3 3 -4 0.0231

_exptl_crystal_recrystallization_method 'Used as received'
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.053
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
1.0048 0.0049 0.9967 0.1075 -0.0646 0.2175
-1.0048 -0.0049 -0.9967 -0.1075 0.0646 -0.2175
0.0003 -0.9995 0.9982 -0.0661 -0.1223 0.1330
-0.0003 0.9995 -0.9982 0.0661 0.1223 -0.1330
0.0015 1.0022 1.0005 0.0347 0.1113 0.1536
0.4905 -6.0356 -4.6055 -0.1701 -0.7076 -0.6846
2.5472 -3.7535 -6.6404 0.2291 -0.5517 -0.8005
-2.5202 3.7083 6.6538 -0.2282 0.5448 0.8040
5.7336 -0.5733 -6.4670 0.7766 -0.3704 -0.5069
-5.4578 0.5957 6.7043 -0.7455 0.3553 0.5616
2.9299 3.9617 3.9706 0.4950 0.2663 0.8266
-4.0189 -5.6126 -1.0479 -0.7580 -0.4110 -0.5053
4.1537 5.9834 -3.7034 0.8688 0.4730 -0.1618
-3.0553 2.8905 -4.3728 -0.1594 0.5432 -0.8243

_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.852
_diffrn_reflns_theta_min         4.450
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(12)
_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 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    127.00 152.00   0.50    0.58    --  113.25  61.00  90.00   50
  2  ω    141.00 167.00   0.50    0.58    --  113.25  61.00  60.00   52
  3  ω    123.00 175.00   0.50    0.58    --  113.25  45.00 -60.00  104
  4  ω    123.00 178.00   0.50    0.58    --  113.25  45.00-120.00  110
  5  ω    125.00 160.00   0.50    0.58    --  113.25  45.00-180.00   70
  6  ω    122.00 176.00   0.50    0.58    --  113.25  45.00-150.00  108
  7  ω    -43.00 -17.00   0.50    0.15    --  -48.10 124.00 -73.00   52
  8  ω    -76.00 -50.00   0.50    0.58    --  -91.75 124.00 -73.00   52
  9  ω    -86.00 -61.00   0.50    0.58    --  -91.75 146.00  92.00   50
 10  ω    -46.00 -21.00   0.50    0.58    --  -91.75  45.00 150.00   50
 11  ω    -42.00  25.00   0.50    0.15    --  -48.10  37.00  60.00  134
 12  ω    -43.00  16.00   0.50    0.15    --  -48.10  37.00 -60.00  118
 13  ω    110.00 150.00   0.50    0.58    --  113.25 124.00 -73.00   80
 14  ω     43.00  69.00   0.50    0.58    --  113.25 -61.00 -90.00   52
 15  ω     44.00  70.00   0.50    0.58    --  113.25 -61.00-120.00   52
 16  ω     44.00  69.00   0.50    0.58    --  113.25 -61.00-180.00   50
 17  ω     43.00  68.00   0.50    0.58    --  113.25 -61.00-150.00   50
 18  ω     42.00  69.00   0.50    0.58    --  113.25 -61.00   0.00   54
 19  ω    -25.00   1.00   0.50    0.15    --   48.10 -19.00 120.00   52
 20  ω     45.00  70.00   0.50    0.58    --  113.25 -61.00 150.00   50
 21  ω     54.00  79.00   0.50    0.15    --   48.10-146.00  41.00   50
 22  ω     51.00  83.00   0.50    0.58    --  113.25-146.00  41.00   64
 23  ω     88.00 124.00   0.50    0.58    --  113.25-146.00  41.00   72
 24  ω     43.00  93.00   0.50    0.58    --  113.25 -94.00 -90.00  100
 25  ω     43.00 102.00   0.50    0.58    --  113.25 -94.00-150.00  118
 26  ω     77.00 102.00   0.50    0.58    --  113.25 -94.00-180.00   50
 27  ω     74.00 100.00   0.50    0.58    --  113.25-124.00-152.00   52
 28  ω     79.00 104.00   0.50    0.58    --  113.25 -94.00-120.00   50
 29  ω     42.00  73.00   0.50    0.58    --  113.25 -94.00-120.00   62
 30  ω     45.00  70.00   0.50    0.58    --  113.25 -94.00 -30.00   50
 31  ω     55.00  90.00   0.50    0.15    --   48.10-124.00-152.00   70
 32  ω   -152.00-127.00   0.50    0.58    --  -91.75 -77.00 -60.00   50
 33  ω   -120.00 -62.00   0.50    0.15    --  -48.10-146.00  41.00  116
 34  ω   -129.00-104.00   0.50    0.58    --  -91.75-146.00  41.00   50
 35  ω   -120.00 -95.00   0.50    0.58    --  -91.75-124.00-152.00   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      0.1225241000
_diffrn_orient_matrix_UB_12      0.0502889000
_diffrn_orient_matrix_UB_13      -0.0159210000
_diffrn_orient_matrix_UB_21      -0.0592873000
_diffrn_orient_matrix_UB_22      0.1167262000
_diffrn_orient_matrix_UB_23      -0.0056356000
_diffrn_orient_matrix_UB_31      0.0742460000
_diffrn_orient_matrix_UB_32      0.0101123000
_diffrn_orient_matrix_UB_33      0.1433124000
_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                2696
_reflns_number_total             2983
_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.062
_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)+(0.0448P)²+0.5915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0890
_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 0.55093(11) 0.12533(8) 0.21447(10) 0.0236(2) Uani 1 1 d . . . . .
O2 O 0.35984(11) 0.18752(9) 0.07597(9) 0.0246(2) Uani 1 1 d . . . . .
O3 O 0.40698(10) 0.44372(9) 0.06540(9) 0.0219(2) Uani 1 1 d . . . . .
O4 O 0.28875(10) 0.39428(10) 0.17058(10) 0.0260(2) Uani 1 1 d . . . . .
O5 O 0.53505(10) 0.38645(8) 0.41822(9) 0.0204(2) Uani 1 1 d . . . . .
O6 O 0.44173(11) 0.22316(9) 0.37173(9) 0.0244(2) Uani 1 1 d . . . . .
N1 N 0.67912(11) 0.44481(9) 0.27211(10) 0.0140(2) Uani 1 1 d . . . . .
N2 N 0.62532(11) 0.34634(9) 0.22337(10) 0.0137(2) Uani 1 1 d . . . . .
N3 N 0.66206(11) 0.30551(9) 0.13395(10) 0.0141(2) Uani 1 1 d . . . . .
N4 N 0.87220(11) 0.62378(9) 0.35140(11) 0.0152(2) Uani 1 1 d . . . . .
H4 H 0.876(2) 0.6046(18) 0.426(2) 0.034(5) Uiso 1 1 d . . . . .
N5 N 0.92381(12) 0.72123(10) 0.33910(11) 0.0183(2) Uani 1 1 d . . . . .
N6 N 0.91664(12) 0.72571(10) 0.22565(11) 0.0184(2) Uani 1 1 d . . . . .
N7 N 0.86206(12) 0.63125(9) 0.16203(11) 0.0167(2) Uani 1 1 d . . . . .
N8 N 0.91635(12) 0.42380(9) 0.04253(10) 0.0160(2) Uani 1 1 d . . . . .
N9 N 0.94239(12) 0.37397(10) -0.04659(11) 0.0169(2) Uani 1 1 d . . . . .
H9 H 1.007(2) 0.3955(18) -0.0700(19) 0.032(5) Uiso 1 1 d . . . . .
N10 N 0.86696(12) 0.28702(10) -0.09608(11) 0.0197(2) Uani 1 1 d . . . . .
N11 N 0.78471(12) 0.27765(10) -0.03848(10) 0.0183(2) Uani 1 1 d . . . . .
N12 N 0.46745(12) 0.19604(10) 0.16467(11) 0.0179(2) Uani 1 1 d . . . . .
N13 N 0.38660(11) 0.39176(10) 0.14477(10) 0.0173(2) Uani 1 1 d . . . . .
N14 N 0.49441(11) 0.30601(10) 0.35253(10) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.76121(13) 0.46528(11) 0.21594(11) 0.0136(2) Uani 1 1 d . . . . .
C2 C 0.75040(13) 0.37866(10) 0.12991(11) 0.0131(2) Uani 1 1 d . . . . .
C3 C 0.83439(13) 0.56976(11) 0.24248(12) 0.0140(2) Uani 1 1 d . . . . .
C4 C 0.81713(13) 0.36118(11) 0.04500(12) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.50162(13) 0.31138(11) 0.22369(11) 0.0145(3) Uani 1 1 d . . . . .
O7 O 0.91239(11) 0.57481(9) 0.58740(9) 0.0203(2) Uani 1 1 d . . . . .
H7 H 0.917(2) 0.6362(19) 0.628(2) 0.031(5) Uiso 1 1 d . . . . .
C6 C 0.82497(16) 0.50160(13) 0.61737(15) 0.0243(3) Uani 1 1 d . . . . .
H6A H 0.822(2) 0.431(2) 0.574(2) 0.040(6) Uiso 1 1 d . . . . .
H6B H 0.864(2) 0.4888(19) 0.707(2) 0.042(6) Uiso 1 1 d . . . . .
H6C H 0.737(2) 0.5321(19) 0.591(2) 0.038(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 N12 1.2101(17) . ?
O2 N12 1.2128(16) . ?
O3 N13 1.2107(15) . ?
O4 N13 1.2161(16) . ?
O5 N14 1.2058(15) . ?
O6 N14 1.2177(16) . ?
N1 N2 1.3463(15) . ?
N1 C1 1.3254(16) . ?
N2 N3 1.3515(15) . ?
N2 C5 1.4096(16) . ?
N3 C2 1.3192(17) . ?
N4 H4 0.88(2) . ?
N4 N5 1.3366(16) . ?
N4 C3 1.3373(17) . ?
N5 N6 1.2952(17) . ?
N6 N7 1.3602(16) . ?
N7 C3 1.3232(17) . ?
N8 N9 1.3269(16) . ?
N8 C4 1.3264(17) . ?
N9 H9 0.89(2) . ?
N9 N10 1.3139(17) . ?
N10 N11 1.3216(16) . ?
N11 C4 1.3470(17) . ?
N12 C5 1.5325(17) . ?
N13 C5 1.5565(17) . ?
N14 C5 1.5376(16) . ?
C1 C2 1.4218(18) . ?
C1 C3 1.4569(18) . ?
C2 C4 1.4595(17) . ?
O7 H7 0.87(2) . ?
O7 C6 1.4401(18) . ?
C6 H6A 0.99(2) . ?
C6 H6B 0.97(2) . ?
C6 H6C 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 102.71(10) . . ?
N1 N2 N3 115.82(10) . . ?
N1 N2 C5 121.02(11) . . ?
N3 N2 C5 118.11(10) . . ?
C2 N3 N2 103.20(10) . . ?
N5 N4 H4 118.7(14) . . ?
N5 N4 C3 108.02(11) . . ?
C3 N4 H4 133.0(14) . . ?
N6 N5 N4 106.95(11) . . ?
N5 N6 N7 110.84(11) . . ?
C3 N7 N6 104.95(10) . . ?
C4 N8 N9 100.94(11) . . ?
N8 N9 H9 123.5(14) . . ?
N10 N9 N8 114.52(11) . . ?
N10 N9 H9 121.9(14) . . ?
N9 N10 N11 105.93(11) . . ?
N10 N11 C4 105.67(11) . . ?
O1 N12 O2 128.82(12) . . ?
O1 N12 C5 115.33(11) . . ?
O2 N12 C5 115.83(11) . . ?
O3 N13 O4 128.60(12) . . ?
O3 N13 C5 115.17(11) . . ?
O4 N13 C5 116.23(11) . . ?
O5 N14 O6 128.65(11) . . ?
O5 N14 C5 115.92(10) . . ?
O6 N14 C5 115.31(11) . . ?
N1 C1 C2 109.33(11) . . ?
N1 C1 C3 118.34(11) . . ?
C2 C1 C3 132.11(12) . . ?
N3 C2 C1 108.80(11) . . ?
N3 C2 C4 119.65(11) . . ?
C1 C2 C4 131.56(12) . . ?
N4 C3 C1 123.85(12) . . ?
N7 C3 N4 109.22(11) . . ?
N7 C3 C1 126.61(12) . . ?
N8 C4 N11 112.93(11) . . ?
N8 C4 C2 124.21(12) . . ?
N11 C4 C2 122.86(12) . . ?
N2 C5 N12 109.24(10) . . ?
N2 C5 N13 110.46(10) . . ?
N2 C5 N14 116.09(10) . . ?
N12 C5 N13 108.11(10) . . ?
N12 C5 N14 107.58(10) . . ?
N14 C5 N13 105.03(10) . . ?
C6 O7 H7 106.7(15) . . ?
O7 C6 H6A 107.2(14) . . ?
O7 C6 H6B 108.4(14) . . ?
O7 C6 H6C 110.9(14) . . ?
H6A C6 H6B 108.8(19) . . ?
H6A C6 H6C 110.5(19) . . ?
H6B C6 H6C 110.9(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O7 0.88(2) 1.80(2) 2.6740(15) 170(2) . yes
N9 H9 N8 0.89(2) 2.31(2) 2.8756(17) 121.2(17) 3_765 yes
O7 H7 N6 0.87(2) 2.02(2) 2.8903(16) 176(2) 4_576 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 N12 C5 N2 57.52(14) . . . . ?
O1 N12 C5 N13 177.76(10) . . . . ?
O1 N12 C5 N14 -69.30(13) . . . . ?
O2 N12 C5 N2 -123.64(12) . . . . ?
O2 N12 C5 N13 -3.39(14) . . . . ?
O2 N12 C5 N14 109.55(12) . . . . ?
O3 N13 C5 N2 24.02(15) . . . . ?
O3 N13 C5 N12 -95.46(13) . . . . ?
O3 N13 C5 N14 149.90(11) . . . . ?
O4 N13 C5 N2 -155.95(12) . . . . ?
O4 N13 C5 N12 84.57(13) . . . . ?
O4 N13 C5 N14 -30.07(15) . . . . ?
O5 N14 C5 N2 48.34(16) . . . . ?
O5 N14 C5 N12 171.03(11) . . . . ?
O5 N14 C5 N13 -73.97(13) . . . . ?
O6 N14 C5 N2 -135.36(12) . . . . ?
O6 N14 C5 N12 -12.67(15) . . . . ?
O6 N14 C5 N13 102.34(13) . . . . ?
N1 N2 N3 C2 3.65(14) . . . . ?
N1 N2 C5 N12 -178.97(10) . . . . ?
N1 N2 C5 N13 62.24(14) . . . . ?
N1 N2 C5 N14 -57.15(15) . . . . ?
N1 C1 C2 N3 -0.12(14) . . . . ?
N1 C1 C2 C4 179.64(13) . . . . ?
N1 C1 C3 N4 29.99(19) . . . . ?
N1 C1 C3 N7 -142.83(13) . . . . ?
N2 N1 C1 C2 2.16(13) . . . . ?
N2 N1 C1 C3 177.46(11) . . . . ?
N2 N3 C2 C1 -1.97(13) . . . . ?
N2 N3 C2 C4 178.24(11) . . . . ?
N3 N2 C5 N12 27.20(15) . . . . ?
N3 N2 C5 N13 -91.59(13) . . . . ?
N3 N2 C5 N14 149.01(11) . . . . ?
N3 C2 C4 N8 -173.23(12) . . . . ?
N3 C2 C4 N11 5.77(19) . . . . ?
N4 N5 N6 N7 -0.77(15) . . . . ?
N5 N4 C3 N7 0.37(15) . . . . ?
N5 N4 C3 C1 -173.52(12) . . . . ?
N5 N6 N7 C3 0.99(15) . . . . ?
N6 N7 C3 N4 -0.81(14) . . . . ?
N6 N7 C3 C1 172.88(12) . . . . ?
N8 N9 N10 N11 0.49(15) . . . . ?
N9 N8 C4 N11 -0.02(14) . . . . ?
N9 N8 C4 C2 179.07(12) . . . . ?
N9 N10 N11 C4 -0.46(14) . . . . ?
N10 N11 C4 N8 0.31(15) . . . . ?
N10 N11 C4 C2 -178.79(12) . . . . ?
C1 N1 N2 N3 -3.70(14) . . . . ?
C1 N1 N2 C5 -158.10(11) . . . . ?
C1 C2 C4 N8 7.0(2) . . . . ?
C1 C2 C4 N11 -173.97(13) . . . . ?
C2 C1 C3 N4 -155.99(14) . . . . ?
C2 C1 C3 N7 31.2(2) . . . . ?
C3 N4 N5 N6 0.25(14) . . . . ?
C3 C1 C2 N3 -174.54(13) . . . . ?
C3 C1 C2 C4 5.2(2) . . . . ?
C4 N8 N9 N10 -0.29(14) . . . . ?
C5 N2 N3 C2 158.83(11) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id A55
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.923
####################################################################### 
# 
# 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_js122b
_database_code_depnum_ccdc_archive 'CCDC 2160567'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 N15'
_chemical_formula_sum            'C6 H5 N15'
_chemical_formula_weight         287.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H5N15
_chemical_oxdiff_usercomment     A108
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.7851(2)
_cell_length_b                   19.1953(5)
_cell_length_c                   7.21396(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.659(2)
_cell_angle_gamma                90
_cell_volume                     1076.87(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4069
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.8410
_cell_measurement_theta_min      4.5780
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    1.165
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0094
-1 0 0 0.0057
0 10 3 0.1308
0 0 5 0.0840
0 6 -4 0.0957
0 -9 -3 0.1289
0 -12 0 0.1110

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.015
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0012 0.0087 0.0003 0.0148 0.1976 0.0071
-1.0012 -0.0087 -0.0003 -0.0148 -0.1976 -0.0071
-0.1242 10.1226 2.7063 -0.5167 0.0132 0.8520
0.0421 0.1400 4.6688 0.3865 -0.0068 0.9208
-0.1087 6.0256 -4.0758 -0.7906 0.0202 -0.6089
0.1217 -8.9022 -3.2394 0.3817 -0.0063 -0.9178
0.1747 -12.4619 -0.0278 0.9168 -0.0231 -0.4005

_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            7366
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.032
_diffrn_reflns_theta_min         4.607
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  25.00   0.50    0.60    --  -48.10  92.00  53.00   72
  2  ω    -78.00 -21.00   0.50    0.60    --  -48.10  92.00  53.00  114
  3  ω      4.00  42.00   0.50    0.60    --   48.10 -92.00 -59.00   76
  4  ω    -72.00 -47.00   0.50    2.40    --  -91.75  92.00  53.00   50
  5  ω    106.00 145.00   0.50    2.40    --  113.25  92.00  53.00   78
  6  ω     45.00  94.00   0.50    2.40    --  113.25 -92.00 -59.00   98
  7  ω    -58.00  22.00   0.50    0.60    --  -48.10  50.00-119.45  160
  8  ω    -25.00   9.00   0.50    0.60    --  -48.10  19.00 150.00   68
  9  ω    -17.00  20.00   0.50    0.60    --   48.10 -19.00  30.00   74
 10  ω    -13.00  23.00   0.50    0.60    --   48.10 -19.00-120.00   72
 11  ω   -156.00-118.00   0.50    2.40    --  -91.75 -92.00 -59.00   76
 12  ω    -51.00 -23.00   0.50    2.40    --  -91.75  45.00-150.00   56
 13  ω    153.00 178.00   0.50    2.40    --  113.25 125.00   0.00   50
 14  ω    110.00 146.00   0.50    2.40    --  113.25 125.00   0.00   72
 15  ω    122.00 177.00   0.50    2.40    --  113.25  45.00-180.00  110
 16  ω     47.00  86.00   0.50    2.40    --  113.25 -77.00 -30.00   78
 17  ω     42.00  70.00   0.50    2.40    --  113.25 -61.00-180.00   56
 18  ω    128.00 176.00   0.50    2.40    --  113.25  77.00  30.00   96
 19  ω     43.00  68.00   0.50    2.40    --  113.25 -61.00  30.00   50
 20  ω    131.00 156.00   0.50    2.40    --  113.25  77.00   0.00   50
 21  ω     44.00  69.00   0.50    2.40    --  113.25 -61.00 150.00   50
 22  ω     43.00 100.00   0.50    2.40    --  113.25 -77.00   0.00  114
 23  ω    108.00 135.00   0.50    2.40    --  113.25 125.00 120.00   54
 24  ω     42.00  67.00   0.50    2.40    --  113.25 -61.00  90.00   50
 25  ω     44.00  70.00   0.50    2.40    --  113.25 -61.00-120.00   52
 26  ω     46.00  76.00   0.50    2.40    --  113.25 -94.00-120.00   60
 27  ω     79.00 104.00   0.50    2.40    --  113.25 -94.00-120.00   50
 28  ω     43.00 103.00   0.50    2.40    --  113.25 -77.00  90.00  120
 29  ω    136.00 166.00   0.50    2.40    --  113.25  77.00 120.00   60
;
_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      0.0153791000
_diffrn_orient_matrix_UB_12      -0.0735421000
_diffrn_orient_matrix_UB_13      0.0848493000
_diffrn_orient_matrix_UB_21      0.1973724000
_diffrn_orient_matrix_UB_22      0.0046321000
_diffrn_orient_matrix_UB_23      -0.0033759000
_diffrn_orient_matrix_UB_31      0.0067575000
_diffrn_orient_matrix_UB_32      0.0317947000
_diffrn_orient_matrix_UB_33      0.1962188000
_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                1990
_reflns_number_total             2263
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.056
_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)+(0.0648P)²+0.3538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1100
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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
N1 N 0.12065(16) 0.38715(6) 0.43283(17) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.20199(16) 0.44569(7) 0.39213(16) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.19928(16) 0.32828(7) 0.39338(17) 0.0194(3) Uani 1 1 d . . . . .
N4 N 0.09483(17) 0.33496(7) 0.81490(17) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.193(3) 0.3179(11) 0.779(3) 0.028(5) Uiso 1 1 d . . . . .
N5 N 0.05809(17) 0.33307(7) 0.99506(17) 0.0240(3) Uani 1 1 d . . . . .
N6 N -0.08148(18) 0.36807(7) 1.01114(18) 0.0233(3) Uani 1 1 d . . . . .
N7 N -0.13738(17) 0.39400(7) 0.84357(17) 0.0201(3) Uani 1 1 d . . . . .
N8 N 0.45238(17) 0.53761(7) 0.21580(18) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.353(3) 0.5616(13) 0.202(3) 0.039(6) Uiso 1 1 d . . . . .
N9 N 0.60414(17) 0.56404(7) 0.16711(18) 0.0230(3) Uani 1 1 d . . . . .
N10 N 0.71625(17) 0.51412(7) 0.18166(18) 0.0222(3) Uani 1 1 d . . . . .
N11 N 0.64022(16) 0.45434(7) 0.23886(17) 0.0202(3) Uani 1 1 d . . . . .
N12 N 0.61731(17) 0.30762(7) 0.18741(17) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.681(3) 0.3477(14) 0.176(3) 0.039(6) Uiso 1 1 d . . . . .
N13 N 0.68165(17) 0.24541(7) 0.13784(18) 0.0222(3) Uani 1 1 d . . . . .
N14 N 0.56487(17) 0.19940(7) 0.17015(18) 0.0225(3) Uani 1 1 d . . . . .
N15 N 0.42436(16) 0.23007(7) 0.24023(17) 0.0202(3) Uani 1 1 d . . . . .
C1 C -0.04377(19) 0.38639(8) 0.5202(2) 0.0212(3) Uani 1 1 d . . . . .
H1A H -0.117720 0.349905 0.461210 0.025 Uiso 1 1 calc R U . . .
H1B H -0.101511 0.431838 0.499060 0.025 Uiso 1 1 calc R U . . .
C2 C -0.02538(19) 0.37282(7) 0.7242(2) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.34634(19) 0.42264(8) 0.31917(18) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.34434(19) 0.34957(8) 0.31939(19) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.47709(19) 0.47052(8) 0.25841(19) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.46048(19) 0.29727(8) 0.24977(19) 0.0182(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3292(18) . ?
N1 N3 1.3224(17) . ?
N1 C1 1.4529(19) . ?
N2 C3 1.3382(19) . ?
N3 C4 1.3354(19) . ?
N4 H4 0.88(2) . ?
N4 N5 1.3442(18) . ?
N4 C2 1.3322(19) . ?
N5 N6 1.2873(19) . ?
N6 N7 1.3599(19) . ?
N7 C2 1.3177(19) . ?
N8 H8 0.90(3) . ?
N8 N9 1.3473(18) . ?
N8 C5 1.3359(19) . ?
N9 N10 1.2971(19) . ?
N10 N11 1.3638(18) . ?
N11 C5 1.3212(19) . ?
N12 H12 0.92(3) . ?
N12 N13 1.3495(18) . ?
N12 C6 1.3355(19) . ?
N13 N14 1.2964(19) . ?
N14 N15 1.3602(18) . ?
N15 C6 1.3213(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.495(2) . ?
C3 C4 1.403(2) . ?
C3 C5 1.454(2) . ?
C4 C6 1.456(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 122.87(12) . . ?
N3 N1 N2 116.41(12) . . ?
N3 N1 C1 120.71(12) . . ?
N1 N2 C3 102.99(12) . . ?
N1 N3 C4 103.47(12) . . ?
N5 N4 H4 119.9(13) . . ?
C2 N4 H4 131.2(13) . . ?
C2 N4 N5 108.25(12) . . ?
N6 N5 N4 106.94(12) . . ?
N5 N6 N7 110.34(12) . . ?
C2 N7 N6 105.88(13) . . ?
N9 N8 H8 122.5(15) . . ?
C5 N8 H8 129.1(15) . . ?
C5 N8 N9 107.72(13) . . ?
N10 N9 N8 107.20(12) . . ?
N9 N10 N11 110.26(12) . . ?
C5 N11 N10 105.50(12) . . ?
N13 N12 H12 120.6(16) . . ?
C6 N12 H12 131.1(16) . . ?
C6 N12 N13 108.30(12) . . ?
N14 N13 N12 106.46(12) . . ?
N13 N14 N15 110.77(12) . . ?
C6 N15 N14 105.61(12) . . ?
N1 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
N1 C1 C2 112.50(12) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
N4 C2 C1 127.69(13) . . ?
N7 C2 N4 108.58(13) . . ?
N7 C2 C1 123.60(14) . . ?
N2 C3 C4 108.70(12) . . ?
N2 C3 C5 121.47(13) . . ?
C4 C3 C5 129.82(13) . . ?
N3 C4 C3 108.43(12) . . ?
N3 C4 C6 118.49(13) . . ?
C3 C4 C6 133.00(13) . . ?
N8 C5 C3 125.69(14) . . ?
N11 C5 N8 109.32(13) . . ?
N11 C5 C3 124.98(13) . . ?
N12 C6 C4 127.28(14) . . ?
N15 C6 N12 108.86(13) . . ?
N15 C6 C4 123.86(13) . . ?

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 C3 C4 0.10(15) . . . . ?
N1 N2 C3 C5 -178.54(13) . . . . ?
N1 N3 C4 C3 0.40(15) . . . . ?
N1 N3 C4 C6 -176.84(12) . . . . ?
N1 C1 C2 N4 -30.7(2) . . . . ?
N1 C1 C2 N7 153.98(14) . . . . ?
N2 N1 N3 C4 -0.37(16) . . . . ?
N2 N1 C1 C2 -99.80(16) . . . . ?
N2 C3 C4 N3 -0.33(16) . . . . ?
N2 C3 C4 C6 176.35(15) . . . . ?
N2 C3 C5 N8 -20.9(2) . . . . ?
N2 C3 C5 N11 158.30(14) . . . . ?
N3 N1 N2 C3 0.17(16) . . . . ?
N3 N1 C1 C2 78.63(17) . . . . ?
N3 C4 C6 N12 -173.31(13) . . . . ?
N3 C4 C6 N15 6.2(2) . . . . ?
N4 N5 N6 N7 -0.67(17) . . . . ?
N5 N4 C2 N7 -0.65(17) . . . . ?
N5 N4 C2 C1 -176.52(14) . . . . ?
N5 N6 N7 C2 0.27(17) . . . . ?
N6 N7 C2 N4 0.25(16) . . . . ?
N6 N7 C2 C1 176.32(13) . . . . ?
N8 N9 N10 N11 0.32(16) . . . . ?
N9 N8 C5 N11 0.38(17) . . . . ?
N9 N8 C5 C3 179.65(13) . . . . ?
N9 N10 N11 C5 -0.08(16) . . . . ?
N10 N11 C5 N8 -0.19(16) . . . . ?
N10 N11 C5 C3 -179.47(13) . . . . ?
N12 N13 N14 N15 0.00(16) . . . . ?
N13 N12 C6 N15 -0.15(16) . . . . ?
N13 N12 C6 C4 179.41(13) . . . . ?
N13 N14 N15 C6 -0.09(16) . . . . ?
N14 N15 C6 N12 0.15(15) . . . . ?
N14 N15 C6 C4 -179.44(13) . . . . ?
C1 N1 N2 C3 178.67(13) . . . . ?
C1 N1 N3 C4 -178.91(13) . . . . ?
C2 N4 N5 N6 0.81(17) . . . . ?
C3 C4 C6 N12 10.3(3) . . . . ?
C3 C4 C6 N15 -170.22(15) . . . . ?
C4 C3 C5 N8 160.82(14) . . . . ?
C4 C3 C5 N11 -20.0(2) . . . . ?
C5 N8 N9 N10 -0.43(16) . . . . ?
C5 C3 C4 N3 178.16(14) . . . . ?
C5 C3 C4 C6 -5.2(3) . . . . ?
C6 N12 N13 N14 0.09(16) . . . . ?

_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 A108
_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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.744
####################################################################### 
# 
# 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_js1221d
_database_code_depnum_ccdc_archive 'CCDC 2160565'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_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 N13 O4, 2(H4 N), H2 O'
_chemical_formula_sum            'C5 H11 N15 O5'
_chemical_formula_weight         361.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C5H9N15O4
_chemical_oxdiff_usercomment     'A55a  needle cut'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.4584(4)
_cell_length_b                   15.8385(3)
_cell_length_c                   13.8004(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.429(4)
_cell_angle_gamma                90
_cell_volume                     2738.34(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6759
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.8600
_cell_measurement_theta_min      3.5440
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    1.336
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (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    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0527
-3 10 1 0.0644
-5 -2 1 0.1118
5 2 -1 0.0985
1 4 -5 0.0458
2 1 -5 0.0454
-2 -1 5 0.0246
2 -5 -2 0.0653
2 4 -5 0.0296
5 1 1 0.0946
1 -5 -2 0.0467
-3 2 -5 0.0882

_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -1.0000 -0.0000 -0.0040 0.0334 0.0913
-3.1439 9.5687 0.7029 -0.0052 0.0198 -0.9998
-4.9996 -2.0002 0.9990 -0.0921 0.6061 -0.0182
4.9996 2.0002 -0.9990 0.0921 -0.6061 0.0182
1.0001 4.0000 -5.0001 -0.5417 -0.2298 -0.3548
2.0000 1.0000 -4.9999 -0.5131 -0.2381 -0.0394
-2.0000 -1.0000 4.9999 0.5131 0.2381 0.0394
2.0000 -5.0000 -1.9998 -0.1782 -0.0451 0.5271
2.0000 4.0000 -4.9999 -0.5010 -0.3381 -0.3134
4.9995 1.0002 1.0011 0.3275 -0.5776 0.1218
1.0000 -5.0000 -2.0000 -0.2189 0.0632 0.4857
-2.9995 1.9999 -5.0010 -0.7127 0.2704 -0.3377

_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9645
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.039
_diffrn_reflns_theta_min         4.432
_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 0.994
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    138.00 171.00   0.50    0.65    --  113.25  61.00  30.00   66
  2  ω    123.00 167.00   0.50    0.65    --  113.25  45.00 -60.00   88
  3  ω    134.00 160.00   0.50    0.65    --  113.25  77.00-180.00   52
  4  ω    127.00 156.00   0.50    0.65    --  113.25  77.00-150.00   58
  5  ω    132.00 168.00   0.50    0.65    --  113.25  45.00 -90.00   72
  6  ω    102.00 171.00   0.50    0.65    --  113.25  30.00  30.00  138
  7  ω    101.00 168.00   0.50    0.65    --  113.25  26.00  -1.00  134
  8  ω    126.00 164.00   0.50    0.65    --  113.25  45.00  90.00   76
  9  ω    152.00 178.00   0.50    0.65    --  113.25  30.00  90.00   52
 10  ω    111.00 141.00   0.50    0.65    --  113.25  30.00  90.00   60
 11  ω     47.00 108.00   0.50    0.16    --   47.85  26.00  -1.00  122
 12  ω    -26.00  26.00   0.50    0.16    --  -47.85  26.00  -1.00  104
 13  ω    -68.00 -41.00   0.50    0.65    --  -91.75 125.00  60.00   54
 14  ω   -111.00 -86.00   0.50    0.65    --  -91.75 -26.00-164.00   50
 15  ω   -122.00 -36.00   0.50    0.16    --  -47.85 -26.00-164.00  172
 16  ω     44.00  70.00   0.50    0.65    --  113.25 -61.00  30.00   52
 17  ω     42.00  67.00   0.50    0.65    --  113.25 -61.00  90.00   50
 18  ω     43.00  68.00   0.50    0.65    --  113.25 -61.00 150.00   50
 19  ω    -20.00  24.00   0.50    0.16    --   47.85 -19.00  60.00   88
 20  ω     42.00  70.00   0.50    0.65    --  113.25 -61.00   0.00   56
 21  ω     42.00  68.00   0.50    0.65    --  113.25 -61.00-120.00   52
 22  ω      1.00  28.00   0.50    0.16    --   47.85 -26.00-164.00   54
 23  ω     63.00 104.00   0.50    0.65    --  113.25 -94.00 -30.00   82
 24  ω     45.00  94.00   0.50    0.65    --  113.25 -94.00   0.00   98
 25  ω     49.00  97.00   0.50    0.65    --  113.25 -94.00  90.00   96
 26  ω     76.00 102.00   0.50    0.65    --  113.25 -94.00  60.00   52
 27  ω     42.00  68.00   0.50    0.65    --  113.25 -94.00  60.00   52
 28  ω     37.00  82.00   0.50    0.16    --   47.85-125.00  30.00   90
 29  ω     81.00 108.00   0.50    0.65    --  113.25-125.00-180.00   54
 30  ω     51.00  77.00   0.50    0.65    --  113.25-125.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0407162000
_diffrn_orient_matrix_UB_12      0.0040415000
_diffrn_orient_matrix_UB_13      0.1197139000
_diffrn_orient_matrix_UB_21      -0.1083658000
_diffrn_orient_matrix_UB_22      -0.0333591000
_diffrn_orient_matrix_UB_23      -0.0024053000
_diffrn_orient_matrix_UB_31      0.0414080000
_diffrn_orient_matrix_UB_32      -0.0913337000
_diffrn_orient_matrix_UB_33      0.0061691000
_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          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2590
_reflns_number_total             2888
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2888
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.109
_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)+(0.0755P)²+2.0651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1276
_refine_special_details          
'All hydrogens were found by difference Fourier methods and refined isotropicall.  Those on N11 and N7 were refined at 50 percent occupancy.'
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H7(0.5) H11(0.5)
;
_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 0.26075(10) 0.47445(8) 0.28272(9) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.32490(10) 0.44965(8) 0.44905(9) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.52200(10) 0.40018(8) 0.52406(9) 0.0267(3) Uani 1 1 d . . . . .
O4 O 0.60006(11) 0.38552(9) 0.41180(11) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.42829(11) 0.51345(8) 0.20812(10) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.43384(12) 0.43797(8) 0.25334(10) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.41574(11) 0.37136(8) 0.18895(10) 0.0196(3) Uani 1 1 d . . . . .
N4 N 0.37380(13) 0.26952(9) 0.00224(11) 0.0250(3) Uani 1 1 d . . . . .
N5 N 0.35433(13) 0.24787(9) -0.09792(11) 0.0270(3) Uani 1 1 d . . . . .
N6 N 0.34772(12) 0.31564(9) -0.15370(11) 0.0233(3) Uani 1 1 d . . . . .
N7 N 0.36307(11) 0.38284(9) -0.09033(10) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.361(3) 0.434(3) -0.108(3) 0.010(8) Uiso 0.5 1 d . . P A 1
N8 N 0.38675(11) 0.64473(8) 0.05124(11) 0.0211(3) Uani 1 1 d . . . . .
N9 N 0.36272(12) 0.68269(9) -0.04206(11) 0.0241(3) Uani 1 1 d . . . . .
N10 N 0.34902(12) 0.62621(9) -0.11482(11) 0.0245(3) Uani 1 1 d . . . . .
N11 N 0.36419(12) 0.54916(9) -0.07002(11) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.360(3) 0.500(3) -0.102(3) 0.022(10) Uiso 0.5 1 d . . P B 2
N12 N 0.33634(11) 0.45218(8) 0.36442(10) 0.0210(3) Uani 1 1 d . . . . .
N13 N 0.52119(12) 0.40487(9) 0.43402(11) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.40579(12) 0.49537(9) 0.10824(11) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.39924(12) 0.40595(9) 0.09649(11) 0.0170(3) Uani 1 1 d . . . . .
C3 C 0.37919(13) 0.35342(9) 0.00485(12) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.38714(12) 0.56234(9) 0.03146(12) 0.0176(3) Uani 1 1 d . . . . .
C5 C 0.43106(13) 0.43204(10) 0.35333(12) 0.0213(3) Uani 1 1 d . . . . .
N14 N 0.61592(13) 0.63806(10) 0.35009(12) 0.0255(3) Uani 1 1 d . . . . .
H14A H 0.634(2) 0.6590(19) 0.297(2) 0.050(8) Uiso 1 1 d . . . . .
H14B H 0.660(3) 0.598(2) 0.382(2) 0.054(8) Uiso 1 1 d . . . . .
H14C H 0.611(2) 0.6777(18) 0.394(2) 0.041(7) Uiso 1 1 d . . . . .
H14D H 0.548(3) 0.613(2) 0.324(3) 0.063(9) Uiso 1 1 d . . . . .
N15 N 0.27342(13) 0.65820(10) 0.34287(13) 0.0281(3) Uani 1 1 d . . . . .
H15A H 0.322(2) 0.6698(18) 0.311(2) 0.048(7) Uiso 1 1 d . . . . .
H15B H 0.213(3) 0.692(2) 0.330(3) 0.073(10) Uiso 1 1 d . . . . .
H15C H 0.310(3) 0.6578(19) 0.410(3) 0.050(8) Uiso 1 1 d . . . . .
H15D H 0.255(3) 0.601(3) 0.317(3) 0.076(10) Uiso 1 1 d . . . . .
O1S O 0.59237(11) 0.22927(8) 0.26502(10) 0.0264(3) Uani 1 1 d . . . . .
H1SA H 0.590(2) 0.207(2) 0.314(3) 0.050(8) Uiso 1 1 d . . . . .
H1SB H 0.545(2) 0.273(2) 0.253(2) 0.051(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N12 1.2620(19) . ?
O2 N12 1.2332(19) . ?
O3 N13 1.2409(19) . ?
O4 N13 1.246(2) . ?
N1 N2 1.3379(18) . ?
N1 C1 1.330(2) . ?
N2 N3 1.3430(18) . ?
N2 C5 1.397(2) . ?
N3 C2 1.3305(19) . ?
N4 N5 1.354(2) . ?
N4 C3 1.331(2) . ?
N5 N6 1.305(2) . ?
N6 N7 1.3446(19) . ?
N7 H7 0.84(4) . ?
N7 C3 1.335(2) . ?
N8 N9 1.3489(19) . ?
N8 C4 1.334(2) . ?
N9 N10 1.307(2) . ?
N10 N11 1.3494(19) . ?
N11 H11 0.88(5) . ?
N11 C4 1.336(2) . ?
N12 C5 1.376(2) . ?
N13 C5 1.382(2) . ?
C1 C2 1.425(2) . ?
C1 C4 1.455(2) . ?
C2 C3 1.454(2) . ?
N14 H14A 0.91(3) . ?
N14 H14B 0.87(3) . ?
N14 H14C 0.89(3) . ?
N14 H14D 0.94(4) . ?
N15 H15A 0.93(3) . ?
N15 H15B 0.94(4) . ?
N15 H15C 0.88(3) . ?
N15 H15D 0.97(4) . ?
O1S H1SA 0.77(3) . ?
O1S H1SB 0.92(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 104.11(12) . . ?
N1 N2 N3 115.31(12) . . ?
N1 N2 C5 120.24(13) . . ?
N3 N2 C5 122.46(13) . . ?
C2 N3 N2 103.74(12) . . ?
C3 N4 N5 105.60(13) . . ?
N6 N5 N4 109.88(13) . . ?
N5 N6 N7 107.83(13) . . ?
N6 N7 H7 126(3) . . ?
C3 N7 N6 107.16(13) . . ?
C3 N7 H7 126(3) . . ?
C4 N8 N9 104.96(13) . . ?
N10 N9 N8 110.22(13) . . ?
N9 N10 N11 108.17(13) . . ?
N10 N11 H11 126(3) . . ?
C4 N11 N10 106.10(13) . . ?
C4 N11 H11 128(3) . . ?
O1 N12 C5 116.28(13) . . ?
O2 N12 O1 121.09(14) . . ?
O2 N12 C5 122.63(14) . . ?
O3 N13 O4 122.35(15) . . ?
O3 N13 C5 120.63(14) . . ?
O4 N13 C5 117.02(14) . . ?
N1 C1 C2 108.26(13) . . ?
N1 C1 C4 120.74(13) . . ?
C2 C1 C4 130.91(14) . . ?
N3 C2 C1 108.57(12) . . ?
N3 C2 C3 120.75(13) . . ?
C1 C2 C3 130.68(13) . . ?
N4 C3 N7 109.53(13) . . ?
N4 C3 C2 125.86(14) . . ?
N7 C3 C2 124.61(14) . . ?
N8 C4 N11 110.54(13) . . ?
N8 C4 C1 125.23(14) . . ?
N11 C4 C1 124.19(14) . . ?
N12 C5 N2 117.04(14) . . ?
N12 C5 N13 123.98(14) . . ?
N13 C5 N2 118.97(15) . . ?
H14A N14 H14B 110(3) . . ?
H14A N14 H14C 113(3) . . ?
H14A N14 H14D 110(3) . . ?
H14B N14 H14C 112(3) . . ?
H14B N14 H14D 106(3) . . ?
H14C N14 H14D 105(3) . . ?
H15A N15 H15B 121(3) . . ?
H15A N15 H15C 107(3) . . ?
H15A N15 H15D 98(3) . . ?
H15B N15 H15C 108(3) . . ?
H15B N15 H15D 112(3) . . ?
H15C N15 H15D 110(3) . . ?
H1SA O1S H1SB 105(3) . . ?

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
N7 H7 O1 0.84(4) 2.46(4) 2.9494(18) 119(3) 2 yes
N7 H7 N11 0.84(4) 1.90(4) 2.649(2) 149(3) . yes
N11 H11 O1 0.88(5) 2.46(4) 3.0392(18) 124(4) 2 yes
N11 H11 N7 0.88(5) 1.87(5) 2.649(2) 146(4) . yes
N14 H14A N6 0.91(3) 2.12(3) 3.015(2) 167(3) 5_665 yes
N14 H14B O1 0.87(3) 2.53(3) 3.027(2) 117(2) 6_665 yes
N14 H14B O2 0.87(3) 2.39(3) 2.939(2) 121(2) 5_666 yes
N14 H14B O2 0.87(3) 2.20(3) 2.983(2) 149(3) 6_665 yes
N14 H14C N4 0.89(3) 2.00(3) 2.881(2) 170(3) 4 yes
N15 H15A O1S 0.93(3) 2.05(3) 2.952(2) 163(3) 4 yes
N15 H15B O1S 0.94(4) 1.98(4) 2.890(2) 163(3) 6_565 yes
N15 H15C O3 0.88(3) 2.30(3) 2.848(2) 121(2) 5_666 yes
N15 H15D O1 0.97(4) 2.07(4) 3.014(2) 164(3) . yes
O1S H1SA N8 0.77(3) 2.03(3) 2.789(2) 170(3) 4_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 N12 C5 N2 -0.2(2) . . . . ?
O1 N12 C5 N13 -178.68(14) . . . . ?
O2 N12 C5 N2 -179.58(14) . . . . ?
O2 N12 C5 N13 2.0(2) . . . . ?
O3 N13 C5 N2 178.83(14) . . . . ?
O3 N13 C5 N12 -2.7(2) . . . . ?
O4 N13 C5 N2 -1.3(2) . . . . ?
O4 N13 C5 N12 177.11(15) . . . . ?
N1 N2 N3 C2 1.10(19) . . . . ?
N1 N2 C5 N12 68.6(2) . . . . ?
N1 N2 C5 N13 -112.82(17) . . . . ?
N1 C1 C2 N3 1.22(18) . . . . ?
N1 C1 C2 C3 -178.48(16) . . . . ?
N1 C1 C4 N8 -2.5(3) . . . . ?
N1 C1 C4 N11 -179.99(15) . . . . ?
N2 N1 C1 C2 -0.52(17) . . . . ?
N2 N1 C1 C4 176.45(14) . . . . ?
N2 N3 C2 C1 -1.34(17) . . . . ?
N2 N3 C2 C3 178.41(14) . . . . ?
N3 N2 C5 N12 -94.60(19) . . . . ?
N3 N2 C5 N13 83.9(2) . . . . ?
N3 C2 C3 N4 0.9(3) . . . . ?
N3 C2 C3 N7 -179.22(15) . . . . ?
N4 N5 N6 N7 0.1(2) . . . . ?
N5 N4 C3 N7 0.33(19) . . . . ?
N5 N4 C3 C2 -179.80(16) . . . . ?
N5 N6 N7 C3 0.09(19) . . . . ?
N6 N7 C3 N4 -0.27(19) . . . . ?
N6 N7 C3 C2 179.86(15) . . . . ?
N8 N9 N10 N11 -0.10(19) . . . . ?
N9 N8 C4 N11 -0.07(18) . . . . ?
N9 N8 C4 C1 -177.89(15) . . . . ?
N9 N10 N11 C4 0.05(18) . . . . ?
N10 N11 C4 N8 0.01(18) . . . . ?
N10 N11 C4 C1 177.85(15) . . . . ?
C1 N1 N2 N3 -0.35(19) . . . . ?
C1 N1 N2 C5 -164.73(15) . . . . ?
C1 C2 C3 N4 -179.40(16) . . . . ?
C1 C2 C3 N7 0.5(3) . . . . ?
C2 C1 C4 N8 173.73(16) . . . . ?
C2 C1 C4 N11 -3.8(3) . . . . ?
C3 N4 N5 N6 -0.3(2) . . . . ?
C4 N8 N9 N10 0.11(18) . . . . ?
C4 C1 C2 N3 -175.34(16) . . . . ?
C4 C1 C2 C3 5.0(3) . . . . ?
C5 N2 N3 C2 165.10(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 A55a
_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.838
####################################################################### 
# 
# 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_js1221g
_database_code_depnum_ccdc_archive 'CCDC 2160566'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2022-03-21 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT129_js1221g             
;
PROBLEM: Unusual Space Group Specified .................. I1a1 Check
RESPONSE: We give the space group I/a as the space group and not C/c 
since the beta angle is less ( 114.35 vs 116.15) and the a axis is also less (23.513 vs 23.865)
 so the correct space group is that which provides the smallest value of Beta.
Monoclinic C  23.865  7.325  20.214  90  116.15  90.
;
_vrf_PLAT416_js1221g             
;
PROBLEM: Short Intra D-H..H-D H1 ..H1C . 1.81 Ang.
RESPONSE: The hydrogn atom H1 on the oxygen O1 was 
refined isotropically to that position and the hydrogen atom H1c of the nitrogen atom N3 were 
placed in calulated postion.  The close porxcimity is the result of H1 refinement that moves 
the hydrogen atom slightly closer towards the atom N1 most likely caused by the Hydrogen 
bonding effects of the nitrogen atom N7B
;
# end Validation Reply Form
_audit_creation_date             2021-12-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 N13 O4, 3(H4 N O), 0.646(H2 O)'
_chemical_formula_sum            'C5 H13.29 N16 O7.65'
_chemical_formula_weight         419.95
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C2H12N16O7
_chemical_oxdiff_usercomment     A55b
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           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   23.5128(5)
_cell_length_b                   7.32460(10)
_cell_length_c                   20.2136(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.350(2)
_cell_angle_gamma                90
_cell_volume                     3171.55(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9499
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6610
_cell_measurement_theta_min      4.1160
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1732
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -4 7 0.0474
9 4 -4 0.0289
7 0 8 0.0204
0 -1 12 0.0221
1 0 -12 0.0127
12 -3 -5 0.0179
-11 3 4 0.0254
-15 -1 6 0.0364
11 2 -11 0.0195
4 4 4 0.0308
-4 -4 -4 0.0386

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.038
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
-6.7530 -3.9066 6.6890 -0.2033 -0.8495 0.4868
8.8963 3.8373 -4.2730 0.2283 0.9518 -0.2050
7.3756 -0.1044 7.8495 0.0900 0.3690 0.9251
0.0179 -0.5691 11.8417 -0.3259 0.0824 0.9401
1.3081 0.2145 -12.3404 0.4284 -0.1072 -0.8954
11.5623 -3.0444 -5.3503 0.9213 -0.2228 0.3103
-11.4928 3.1060 3.6417 -0.8694 0.2097 -0.4414
-14.8507 -1.0836 5.6237 -0.7518 -0.6430 -0.1444
10.6382 1.9259 -10.8517 0.6623 0.5632 -0.4953
3.7487 4.1204 3.8943 -0.2791 0.9462 0.1713
-3.7881 -4.0922 -4.0017 0.2785 -0.9442 -0.1831

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19452
_diffrn_reflns_point_group_measured_fraction_full 0.786
_diffrn_reflns_point_group_measured_fraction_max 0.763
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.881
_diffrn_reflns_theta_min         4.128
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  19.00   0.50    0.96    --  -48.10  19.00 -90.00   54
  2  ω    -25.00  26.00   0.50    0.96    --  -48.10  19.00   0.00  102
  3  ω    -18.00  24.00   0.50    0.96    --  -48.10  19.00-120.00   84
  4  ω    -69.00   0.00   0.50    0.96    --  -48.10  77.00 120.00  138
  5  ω    -82.00 -54.00   0.50    0.96    --  -48.10 125.00 150.00   56
  6  ω     -9.00  26.00   0.50    0.96    --  -48.10  19.00  30.00   70
  7  ω    -23.00  20.00   0.50    0.96    --   48.10 -37.00 -30.00   86
  8  ω    -26.00  24.00   0.50    0.96    --   48.10 -19.00   0.00  100
  9  ω    -14.00  19.00   0.50    0.96    --   48.10 -19.00  90.00   66
 10  ω      0.00  71.00   0.50    0.96    --   48.10 -77.00-120.00  142
 11  ω   -161.00-133.00   0.50    3.83    --  -91.75 -77.00-180.00   56
 12  ω   -159.00-132.00   0.50    3.83    --  -91.75 -61.00 -30.00   54
 13  ω   -145.00-119.00   0.50    3.83    --  -91.75 -15.00   0.00   52
 14  ω    -81.00 -44.00   0.50    3.83    --  -91.75 125.00  30.00   74
 15  ω     61.00  97.00   0.50    3.83    --  113.25 -94.00-180.00   72
 16  ω    101.00 176.00   0.50    3.83    --  113.25  30.00 150.00  150
 17  ω     42.00 103.00   0.50    3.83    --  113.25 -94.00 120.00  122
 18  ω    132.00 168.00   0.50    3.83    --  113.25  61.00  30.00   72
 19  ω     45.00  83.00   0.50    3.83    --  113.25 -97.00-153.10   76
 20  ω     45.00  70.00   0.50    3.83    --  113.25 -61.00 -30.00   50
 21  ω     70.00  95.00   0.50    3.83    --  113.25 -94.00 -90.00   50
 22  ω     44.00 102.00   0.50    3.83    --  113.25 -94.00  90.00  116
 23  ω     48.00  74.00   0.50    3.83    --  113.25 -94.00  30.00   52
 24  ω    100.00 171.00   0.50    3.83    --  113.25  15.00-150.00  142
 25  ω     42.00  68.00   0.50    3.83    --  113.25 -94.00 -90.00   52
 26  ω     44.00  70.00   0.50    3.83    --  113.25 -61.00 120.00   52
 27  ω    128.00 177.00   0.50    3.83    --  113.25  61.00 120.00   98
 28  ω    144.00 170.00   0.50    3.83    --  113.25  45.00  60.00   52
 29  ω    120.00 167.00   0.50    3.83    --  113.25 125.00 150.00   94
 30  ω     42.00  67.00   0.50    3.83    --  113.25 -61.00-120.00   50
 31  ω    101.00 126.00   0.50    3.83    --  113.25  15.00 -60.00   50
 32  ω     68.00 101.00   0.50    3.83    --  113.25 -94.00 -30.00   66
 33  ω     43.00  76.00   0.50    3.83    --  113.25 -77.00 -30.00   66
 34  ω     77.00 102.00   0.50    3.83    --  113.25 -94.00   0.00   50
 35  ω     82.00 108.00   0.50    3.83    --  113.25-125.00-180.00   52
 36  ω    122.00 148.00   0.50    3.83    --  113.25  45.00   0.00   52
 37  ω     50.00  77.00   0.50    3.83    --  113.25-125.00-180.00   54
 38  ω    101.00 155.00   0.50    3.83    --  113.25  30.00-120.00  108
 39  ω     43.00  68.00   0.50    3.83    --  113.25 -61.00 150.00   50
 40  ω    145.00 170.00   0.50    3.83    --  113.25  15.00 -60.00   50
 41  ω    123.00 164.00   0.50    3.83    --  113.25  45.00  90.00   82
 42  ω     49.00  78.00   0.50    3.83    --  113.25-125.00   0.00   58
 43  ω     57.00 104.00   0.50    3.83    --  113.25 -94.00-120.00   94
 44  ω     79.00 104.00   0.50    3.83    --  113.25 -94.00  30.00   50
 45  ω    144.00 177.00   0.50    3.83    --  113.25  77.00-150.00   66
 46  ω     74.00 101.00   0.50    3.83    --  113.25 -94.00 -60.00   54
 47  ω     42.00  94.00   0.50    3.83    --  113.25 -94.00  60.00  104
 48  ω     43.00  69.00   0.50    3.83    --  113.25 -61.00 -90.00   52
 49  ω    122.00 147.00   0.50    3.83    --  113.25  45.00  30.00   50
 50  ω     55.00 105.00   0.50    3.83    --  113.25-106.00-118.68  100
;
_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      0.0444807000
_diffrn_orient_matrix_UB_12      -0.0785572000
_diffrn_orient_matrix_UB_13      -0.0313677000
_diffrn_orient_matrix_UB_21      0.0359389000
_diffrn_orient_matrix_UB_22      0.1821461000
_diffrn_orient_matrix_UB_23      0.0156591000
_diffrn_orient_matrix_UB_31      0.0435869000
_diffrn_orient_matrix_UB_32      -0.0698849000
_diffrn_orient_matrix_UB_33      0.0759657000
_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         0.546
_reflns_Friedel_fraction_full    0.571
_reflns_Friedel_fraction_max     0.539
_reflns_number_gt                4784
_reflns_number_total             5275
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         5275
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.081
_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)+(0.0667P)²+5.9699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1284
_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: 0.6(6)
 0.4(6)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Restrained distances
 N7-O10 \\sim O3-N3
 with sigma of 0.02
 O1W-H1WA \\sim O1W-H1WB
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(O7) = Uanis(O1W) = Uanis(O9)
Uanis(N3) = Uanis(O10) = Uanis(O3) = Uanis(N7)
5. Others
 Sof(O9)=Sof(H9A)=Sof(H9B)=Sof(N7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(O10)=
 Sof(H10)=Sof(O7)=Sof(H7D)=Sof(H7E)=1-FVAR(1)
 Sof(O3)=Sof(H3)=Sof(N3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(O1W)=Sof(H1WA)=
 Sof(H1WB)=FVAR(1)
6.a Riding coordinates:
 O9(H9A,H9B)
6.b Free rotating group:
 O1W(H1WA), O7(H7D,H7E)
6.c Idealised Me refined as rotating group:
 N4(H4A,H4B,H4C), N3(H3A,H3B,H3C), N1(H1A,H1B,H1C), N8(H8A,H8B,H8C), N2(H2A,
 H2B,H2C), N7(H7A,H7B,H7C)
6.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O5(H5), O2(H2), O6(H6), O10(H10)
;
_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
O1A O 0.2214(2) -0.1004(5) 0.1354(2) 0.0188(8) Uani 1 1 d . . . . .
O2A O 0.16750(19) -0.0629(6) 0.0185(2) 0.0198(8) Uani 1 1 d . . . . .
O3A O 0.30341(19) -0.3626(6) -0.0046(2) 0.0199(8) Uani 1 1 d . . . . .
O4A O 0.2191(2) -0.2049(5) -0.0629(2) 0.0176(9) Uani 1 1 d . . . . .
N1A N 0.3554(2) -0.1755(6) 0.1616(3) 0.0130(9) Uani 1 1 d . . . . .
N2A N 0.3083(2) -0.2872(6) 0.1241(3) 0.0132(9) Uani 1 1 d . . . . .
N3A N 0.3081(2) -0.4473(6) 0.1562(2) 0.0149(9) Uani 1 1 d . . . . .
N4A N 0.4713(2) -0.2334(7) 0.3471(3) 0.0176(10) Uani 1 1 d . . . . .
N5A N 0.5179(2) -0.1146(7) 0.3763(3) 0.0181(10) Uani 1 1 d . . . . .
N6A N 0.5179(2) 0.0013(6) 0.3261(3) 0.0180(9) Uani 1 1 d . . . . .
N7A N 0.4707(2) -0.0380(7) 0.2629(2) 0.0164(9) Uani 1 1 d . . . . .
N8A N 0.4240(2) -0.6292(7) 0.3267(3) 0.0257(12) Uani 1 1 d . . . . .
N9A N 0.4118(3) -0.7839(7) 0.3549(3) 0.0243(11) Uani 1 1 d . . . . .
N10A N 0.3556(2) -0.8392(7) 0.3127(3) 0.0200(10) Uani 1 1 d . . . . .
N11A N 0.3290(2) -0.7260(6) 0.2583(3) 0.0161(10) Uani 1 1 d . . . . .
N12A N 0.2140(2) -0.1289(6) 0.0705(3) 0.0151(9) Uani 1 1 d . . . . .
N13A N 0.2594(2) -0.2671(6) -0.0060(2) 0.0134(9) Uani 1 1 d . . . . .
C1A C 0.4433(3) -0.1811(7) 0.2775(3) 0.0126(10) Uani 1 1 d . . . . .
C2A C 0.3875(3) -0.2697(7) 0.2217(3) 0.0132(10) Uani 1 1 d . . . . .
C3A C 0.3588(3) -0.4387(7) 0.2180(3) 0.0127(10) Uani 1 1 d . . . . .
C4A C 0.3722(3) -0.5965(7) 0.2681(3) 0.0147(11) Uani 1 1 d . . . . .
C013 C 0.2581(3) -0.2306(7) 0.0621(3) 0.0148(10) Uani 1 1 d . . . . .
O1B O 0.69663(19) -0.1461(6) 0.5069(2) 0.0197(8) Uani 1 1 d . . . . .
O2B O 0.7824(2) -0.3021(5) 0.5646(2) 0.0178(8) Uani 1 1 d . . . . .
O3B O 0.83260(19) -0.4457(6) 0.4811(2) 0.0196(8) Uani 1 1 d . . . . .
O4B O 0.7779(2) -0.4056(6) 0.3648(2) 0.0213(9) Uani 1 1 d . . . . .
N1B N 0.6927(2) -0.0574(6) 0.3476(2) 0.0132(9) Uani 1 1 d . . . . .
N2B N 0.6914(2) -0.2176(5) 0.3786(3) 0.0136(9) Uani 1 1 d . . . . .
N3B N 0.6440(2) -0.3283(6) 0.3393(2) 0.0128(9) Uani 1 1 d . . . . .
N4B N 0.6734(2) 0.2239(6) 0.2488(3) 0.0158(10) Uani 1 1 d . . . . .
N5B N 0.6469(2) 0.3469(6) 0.1937(3) 0.0174(9) Uani 1 1 d . . . . .
N6B N 0.5893(3) 0.2985(7) 0.1547(3) 0.0235(11) Uani 1 1 d . . . . .
N7B N 0.5765(2) 0.1408(7) 0.1809(3) 0.0218(10) Uani 1 1 d . . . . .
N8B N 0.5269(2) -0.4552(6) 0.2357(2) 0.0134(9) Uani 1 1 d . . . . .
N9B N 0.4802(2) -0.4917(6) 0.1714(3) 0.0163(9) Uani 1 1 d . . . . .
N10B N 0.4819(2) -0.3753(7) 0.1233(3) 0.0202(10) Uani 1 1 d . . . . .
N11B N 0.5307(2) -0.2601(7) 0.1544(3) 0.0161(9) Uani 1 1 d . . . . .
N12B N 0.7871(2) -0.3822(6) 0.4302(3) 0.0143(9) Uani 1 1 d . . . . .
N13B N 0.7416(2) -0.2433(6) 0.5071(3) 0.0154(9) Uani 1 1 d . . . . .
C1B C 0.6296(3) 0.0993(7) 0.2386(3) 0.0150(11) Uani 1 1 d . . . . .
C01E C 0.7416(3) -0.2778(7) 0.4408(3) 0.0120(10) Uani 1 1 d . . . . .
C2B C 0.6419(3) -0.0588(7) 0.2855(3) 0.0136(10) Uani 1 1 d . . . . .
C3B C 0.6110(3) -0.2312(7) 0.2795(3) 0.0116(10) Uani 1 1 d . . . . .
C4B C 0.5566(3) -0.3101(7) 0.2229(3) 0.0129(11) Uani 1 1 d . . . . .
O4 O 0.3314(2) -0.2988(5) 0.3407(3) 0.0226(9) Uani 1 1 d . . . . .
H4 H 0.311481 -0.395616 0.338240 0.034 Uiso 1 1 calc R U . . .
N4 N 0.2965(2) -0.1479(6) 0.3476(2) 0.0136(9) Uani 1 1 d . . . . .
H4A H 0.256079 -0.159081 0.315132 0.016 Uiso 1 1 calc R U . . .
H4B H 0.312817 -0.042756 0.338798 0.016 Uiso 1 1 calc R U . . .
H4C H 0.298345 -0.145000 0.393475 0.016 Uiso 1 1 calc R U . . .
O3 O 0.4320(4) -0.1516(11) 0.4811(6) 0.0252(9) Uani 0.707(6) 1 d D . P A 1
H3 H 0.448803 -0.138051 0.526335 0.038 Uiso 0.707(6) 1 calc R U P A 1
N3 N 0.4390(4) -0.3425(10) 0.4629(4) 0.0252(9) Uani 0.707(6) 1 d D . P A 1
H3A H 0.430808 -0.350836 0.414919 0.030 Uiso 0.707(6) 1 calc R U P A 1
H3B H 0.411781 -0.414175 0.472662 0.030 Uiso 0.707(6) 1 calc R U P A 1
H3C H 0.478742 -0.380433 0.489958 0.030 Uiso 0.707(6) 1 calc R U P A 1
O1 O 0.4566(2) 0.1027(6) 0.0908(2) 0.0204(9) Uani 1 1 d . . . . .
H1 H 0.489(3) 0.090(10) 0.133(4) 0.032(16) Uiso 1 1 d . . . . .
N1 N 0.4213(2) 0.1613(7) 0.1287(3) 0.0168(9) Uani 1 1 d . . . . .
H1A H 0.379948 0.155724 0.098751 0.020 Uiso 1 1 calc R U . . .
H1B H 0.431802 0.278296 0.143923 0.020 Uiso 1 1 calc R U . . .
H1C H 0.429370 0.087647 0.167764 0.020 Uiso 1 1 calc R U . . .
O5 O 0.0343(2) -0.3816(6) 0.0088(3) 0.0430(10) Uani 1 1 d . . . . .
H5 H 0.038061 -0.356108 0.050887 0.065 Uiso 1 1 calc R U . . .
N8 N 0.0823(3) -0.5056(8) 0.0129(3) 0.0363(12) Uani 1 1 d . . . . .
H8A H 0.082273 -0.518541 -0.031887 0.044 Uiso 1 1 calc R U . . .
H8B H 0.075297 -0.615971 0.028826 0.044 Uiso 1 1 calc R U . . .
H8C H 0.119919 -0.461477 0.044353 0.044 Uiso 1 1 calc R U . . .
O2 O 0.5458(2) -0.5983(6) 0.4091(2) 0.0228(9) Uani 1 1 d . . . . .
H2 H 0.507617 -0.592557 0.381685 0.034 Uiso 1 1 calc R U . . .
N2 N 0.5794(2) -0.6588(7) 0.3687(3) 0.0185(10) Uani 1 1 d . . . . .
H2A H 0.567105 -0.593605 0.326776 0.022 Uiso 1 1 calc R U . . .
H2B H 0.571626 -0.779409 0.358076 0.022 Uiso 1 1 calc R U . . .
H2C H 0.621020 -0.642040 0.395437 0.022 Uiso 1 1 calc R U . . .
O6 O 0.1673(2) -0.8031(5) 0.1587(3) 0.0208(9) Uani 1 1 d . . . . .
H6 H 0.179046 -0.897776 0.144459 0.031 Uiso 1 1 calc R U . . .
N6 N 0.2044(2) -0.6544(7) 0.1565(3) 0.0180(10) Uani 1 1 d . . . . .
H6A H 0.249(3) -0.682(9) 0.196(4) 0.030(15) Uiso 1 1 d . . . . .
H6B H 0.189(2) -0.556(7) 0.177(3) 0.010(11) Uiso 1 1 d . . . . .
H6C H 0.198(3) -0.645(7) 0.116(3) 0.011(12) Uiso 1 1 d . . . . .
O1W O 0.5544(3) -0.4597(9) 0.5431(4) 0.0266(7) Uani 0.707(6) 1 d DG . P A 1
H1WA H 0.556422 -0.371284 0.572802 0.040 Uiso 0.707(6) 1 d DG U P A 1
O9 O 0.4460(7) -0.460(2) 0.4578(8) 0.0266(7) Uani 0.293(6) 1 d . . P A 2
H9A H 0.422708 -0.406269 0.476125 0.040 Uiso 0.293(6) 1 d R U P A 2
H9B H 0.483538 -0.420649 0.484035 0.040 Uiso 0.293(6) 1 d R U P A 2
N7 N 0.4162(9) 0.010(2) 0.4884(11) 0.0252(9) Uani 0.293(6) 1 d D . P A 2
H7A H 0.422620 0.076632 0.454183 0.030 Uiso 0.293(6) 1 calc R U P A 2
H7B H 0.445655 0.039057 0.533226 0.030 Uiso 0.293(6) 1 calc R U P A 2
H7C H 0.377610 0.034234 0.486387 0.030 Uiso 0.293(6) 1 calc R U P A 2
O10 O 0.4206(11) -0.177(3) 0.4753(15) 0.0252(9) Uani 0.293(6) 1 d D . P A 2
H10 H 0.387457 -0.211665 0.441099 0.038 Uiso 0.293(6) 1 calc R U P A 2
O7 O 0.5603(8) -0.333(2) 0.5363(9) 0.0266(7) Uani 0.293(6) 1 d G . P A 2
H7D H 0.581343 -0.293038 0.512626 0.040 Uiso 0.293(6) 1 d G U P A 2
H7E H 0.576698 -0.277545 0.578046 0.040 Uiso 0.293(6) 1 d G U P A 2
H1WB H 0.590(3) -0.462(12) 0.538(5) 0.03(2) Uiso 0.707(6) 1 d D . P A 1


_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
O1A N12A 1.268(6) . ?
O2A N12A 1.259(6) . ?
O3A N13A 1.239(6) . ?
O4A N13A 1.237(6) . ?
N1A N2A 1.333(6) . ?
N1A C2A 1.328(7) . ?
N2A N3A 1.341(6) . ?
N2A C013 1.386(7) . ?
N3A C3A 1.325(7) . ?
N4A N5A 1.333(7) . ?
N4A C1A 1.340(7) . ?
N5A N6A 1.323(7) . ?
N6A N7A 1.333(6) . ?
N7A C1A 1.326(7) . ?
N8A N9A 1.351(7) . ?
N8A C4A 1.324(8) . ?
N9A N10A 1.307(8) . ?
N10A N11A 1.312(7) . ?
N11A C4A 1.345(7) . ?
N12A C013 1.343(7) . ?
N13A C013 1.415(7) . ?
C1A C2A 1.481(7) . ?
C2A C3A 1.397(7) . ?
C3A C4A 1.482(7) . ?
O1B N13B 1.273(6) . ?
O2B N13B 1.241(6) . ?
O3B N12B 1.231(6) . ?
O4B N12B 1.259(6) . ?
N1B N2B 1.336(6) . ?
N1B C2B 1.330(7) . ?
N2B N3B 1.343(6) . ?
N2B C01E 1.395(7) . ?
N3B C3B 1.339(7) . ?
N4B N5B 1.366(7) . ?
N4B C1B 1.327(7) . ?
N5B N6B 1.305(7) . ?
N6B N7B 1.355(7) . ?
N7B C1B 1.345(8) . ?
N8B N9B 1.338(6) . ?
N8B C4B 1.355(7) . ?
N9B N10B 1.306(7) . ?
N10B N11B 1.353(7) . ?
N11B C4B 1.314(7) . ?
N12B C01E 1.400(7) . ?
N13B C01E 1.364(7) . ?
C1B C2B 1.448(7) . ?
C2B C3B 1.437(7) . ?
C3B C4B 1.439(7) . ?
O4 H4 0.8400 . ?
O4 N4 1.417(6) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
O3 H3 0.8400 . ?
O3 N3 1.471(12) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
O1 H1 0.89(7) . ?
O1 N1 1.408(6) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
O5 H5 0.8400 . ?
O5 N8 1.423(7) . ?
N8 H8A 0.9100 . ?
N8 H8B 0.9100 . ?
N8 H8C 0.9100 . ?
O2 H2 0.8400 . ?
O2 N2 1.420(6) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
O6 H6 0.8400 . ?
O6 N6 1.407(6) . ?
N6 H6A 1.05(7) . ?
N6 H6B 0.98(5) . ?
N6 H6C 0.78(6) . ?
O1W H1WA 0.8703 . ?
O1W H1WB 0.90(3) . ?
O9 H9A 0.8707 . ?
O9 H9B 0.8702 . ?
N7 H7A 0.9100 . ?
N7 H7B 0.9100 . ?
N7 H7C 0.9100 . ?
N7 O10 1.41(2) . ?
O10 H10 0.8400 . ?
O7 H7D 0.8699 . ?
O7 H7E 0.8699 . ?

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
C2A N1A N2A 103.1(4) . . ?
N1A N2A N3A 115.4(4) . . ?
N1A N2A C013 122.0(4) . . ?
N3A N2A C013 121.9(5) . . ?
C3A N3A N2A 103.5(4) . . ?
N5A N4A C1A 103.8(5) . . ?
N6A N5A N4A 109.8(5) . . ?
N5A N6A N7A 109.4(4) . . ?
C1A N7A N6A 104.4(4) . . ?
C4A N8A N9A 104.7(5) . . ?
N10A N9A N8A 108.5(5) . . ?
N9A N10A N11A 110.8(5) . . ?
N10A N11A C4A 104.6(5) . . ?
O1A N12A C013 116.1(5) . . ?
O2A N12A O1A 120.1(5) . . ?
O2A N12A C013 123.8(5) . . ?
O3A N13A C013 116.0(4) . . ?
O4A N13A O3A 122.8(5) . . ?
O4A N13A C013 121.2(5) . . ?
N4A C1A C2A 124.9(5) . . ?
N7A C1A N4A 112.6(5) . . ?
N7A C1A C2A 122.5(5) . . ?
N1A C2A C1A 117.3(5) . . ?
N1A C2A C3A 109.4(5) . . ?
C3A C2A C1A 133.3(5) . . ?
N3A C3A C2A 108.6(5) . . ?
N3A C3A C4A 117.5(5) . . ?
C2A C3A C4A 133.8(5) . . ?
N8A C4A N11A 111.4(5) . . ?
N8A C4A C3A 127.6(5) . . ?
N11A C4A C3A 121.0(5) . . ?
N2A C013 N13A 118.1(5) . . ?
N12A C013 N2A 117.7(5) . . ?
N12A C013 N13A 123.8(5) . . ?
C2B N1B N2B 104.5(4) . . ?
N1B N2B N3B 115.3(4) . . ?
N1B N2B C01E 121.7(5) . . ?
N3B N2B C01E 122.0(4) . . ?
C3B N3B N2B 104.1(4) . . ?
C1B N4B N5B 105.3(5) . . ?
N6B N5B N4B 108.9(5) . . ?
N5B N6B N7B 109.8(5) . . ?
C1B N7B N6B 104.8(5) . . ?
N9B N8B C4B 104.6(4) . . ?
N10B N9B N8B 109.1(4) . . ?
N9B N10B N11B 110.0(5) . . ?
C4B N11B N10B 104.5(5) . . ?
O3B N12B O4B 122.6(5) . . ?
O3B N12B C01E 122.2(5) . . ?
O4B N12B C01E 115.1(5) . . ?
O1B N13B C01E 116.0(5) . . ?
O2B N13B O1B 121.1(5) . . ?
O2B N13B C01E 122.9(5) . . ?
N4B C1B N7B 111.2(5) . . ?
N4B C1B C2B 121.1(5) . . ?
N7B C1B C2B 127.7(5) . . ?
N2B C01E N12B 116.7(5) . . ?
N13B C01E N2B 118.9(5) . . ?
N13B C01E N12B 124.2(5) . . ?
N1B C2B C1B 118.1(5) . . ?
N1B C2B C3B 108.2(4) . . ?
C3B C2B C1B 133.7(5) . . ?
N3B C3B C2B 107.8(5) . . ?
N3B C3B C4B 119.9(5) . . ?
C2B C3B C4B 132.2(5) . . ?
N8B C4B C3B 121.4(5) . . ?
N11B C4B N8B 111.7(5) . . ?
N11B C4B C3B 126.9(5) . . ?
N4 O4 H4 109.5 . . ?
O4 N4 H4A 109.5 . . ?
O4 N4 H4B 109.5 . . ?
O4 N4 H4C 109.5 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
N3 O3 H3 109.5 . . ?
O3 N3 H3A 109.5 . . ?
O3 N3 H3B 109.5 . . ?
O3 N3 H3C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
N1 O1 H1 88(4) . . ?
O1 N1 H1A 109.5 . . ?
O1 N1 H1B 109.5 . . ?
O1 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N8 O5 H5 109.5 . . ?
O5 N8 H8A 109.5 . . ?
O5 N8 H8B 109.5 . . ?
O5 N8 H8C 109.5 . . ?
H8A N8 H8B 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
N2 O2 H2 109.5 . . ?
O2 N2 H2A 109.5 . . ?
O2 N2 H2B 109.5 . . ?
O2 N2 H2C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N6 O6 H6 109.5 . . ?
O6 N6 H6A 106(3) . . ?
O6 N6 H6B 102(3) . . ?
O6 N6 H6C 105(4) . . ?
H6A N6 H6B 105(5) . . ?
H6A N6 H6C 120(5) . . ?
H6B N6 H6C 117(5) . . ?
H1WA O1W H1WB 108.0 . . ?
H9A O9 H9B 104.5 . . ?
H7A N7 H7B 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
O10 N7 H7A 109.5 . . ?
O10 N7 H7B 109.5 . . ?
O10 N7 H7C 109.5 . . ?
N7 O10 H10 109.5 . . ?
H7D O7 H7E 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
O4 H4 O4B 0.84 1.84 2.648(6) 161.3 2_445 yes
N4 H4A N4B 0.91 1.91 2.814(7) 170.8 2_455 yes
N4 H4B N10A 0.91 1.99 2.889(6) 170.7 1_565 yes
N4 H4C O3A 0.91 2.01 2.924(6) 179.3 4_445 yes
O3 H3 N10B 0.84 1.79 2.627(11) 175.7 4_445 yes
N3 H3A N4A 0.91 2.15 2.857(10) 134.4 . yes
N3 H3A O4 0.91 2.23 2.730(10) 114.1 . yes
N3 H3B O3B 0.91 2.19 3.092(9) 169.2 2_445 yes
N3 H3B O1 0.91 2.58 3.099(9) 117.0 4_445 yes
N3 H3C O1W 0.91 1.75 2.664(11) 178.1 . yes
O1 H1 N7B 0.89(7) 1.91(7) 2.667(7) 141(6) . yes
N1 H1A O2B 0.91 2.13 2.989(6) 157.3 3_454 yes
N1 H1A O3B 0.91 2.29 2.954(6) 129.2 3_454 yes
N1 H1B N9B 0.91 1.98 2.853(6) 160.2 1_565 yes
N1 H1C N7A 0.91 1.99 2.872(7) 163.5 . yes
O5 H5 N6B 0.84 1.99 2.757(7) 151.9 2_455 yes
N8 H8A N5A 0.91 1.98 2.665(8) 131.0 3_444 yes
N8 H8B O7 0.91 1.65 2.539(17) 165.0 3_444 yes
O2 H2 N8A 0.84 1.84 2.664(7) 168.3 . yes
N2 H2A N3B 0.91 2.59 3.043(7) 111.2 . yes
N2 H2A N8B 0.91 1.97 2.870(7) 170.7 . yes
N2 H2B N6A 0.91 1.98 2.829(7) 154.7 1_545 yes
N2 H2C O2A 0.91 2.34 2.963(7) 125.5 3_545 yes
N2 H2C O4A 0.91 2.15 3.012(7) 156.8 3_545 yes
O6 H6 O1A 0.84 1.84 2.659(6) 165.7 1_545 yes
N6 H6A N11A 1.05(7) 1.81(7) 2.850(7) 176(5) . yes
N6 H6B N5B 0.98(5) 1.92(5) 2.880(7) 166(5) 2_455 yes
N6 H6C O1B 0.78(6) 2.18(6) 2.954(7) 170(6) 3_444 yes
O1W H1WA N11B 0.87 2.20 2.998(8) 152.7 4_445 yes
O1W H1WA O6 0.87 2.52 2.951(8) 111.7 3 yes
O9 H9A O3B 0.87 2.42 2.974(15) 122.0 2_445 yes
O9 H9A O10 0.87 1.68 2.22(3) 117.9 . yes
O9 H9B O7 0.87 1.79 2.66(2) 178.1 . yes
N7 H7A N9A 0.91 2.17 3.06(2) 164.5 1_565 yes
N7 H7B N10B 0.91 2.05 2.70(2) 127.8 4_445 yes
N7 H7C O3A 0.91 2.22 2.920(19) 133.5 4_445 yes
O10 H10 O4 0.84 2.01 2.81(2) 157.6 . yes
O10 H10 N4 0.84 2.24 3.00(3) 150.4 . yes
O7 H7D N8 0.87 2.11 2.539(18) 110.1 3 yes
O7 H7E N11B 0.87 2.24 2.830(17) 125.3 4_445 yes
O7 H7E O6 0.87 2.09 2.715(17) 128.1 3 yes
O1W H1WB O2A 0.90(3) 2.14(4) 2.998(7) 160(8) 3_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
O1A N12A C013 N2A -2.8(8) . . . . ?
O1A N12A C013 N13A -176.1(5) . . . . ?
O2A N12A C013 N2A 177.0(5) . . . . ?
O2A N12A C013 N13A 3.7(9) . . . . ?
O3A N13A C013 N2A 6.4(7) . . . . ?
O3A N13A C013 N12A 179.6(5) . . . . ?
O4A N13A C013 N2A -172.9(5) . . . . ?
O4A N13A C013 N12A 0.3(8) . . . . ?
N1A N2A N3A C3A -0.8(6) . . . . ?
N1A N2A C013 N12A -78.0(7) . . . . ?
N1A N2A C013 N13A 95.6(6) . . . . ?
N1A C2A C3A N3A -1.4(6) . . . . ?
N1A C2A C3A C4A -178.8(6) . . . . ?
N2A N1A C2A C1A -178.5(5) . . . . ?
N2A N1A C2A C3A 0.9(6) . . . . ?
N2A N3A C3A C2A 1.2(6) . . . . ?
N2A N3A C3A C4A 179.1(5) . . . . ?
N3A N2A C013 N12A 91.6(6) . . . . ?
N3A N2A C013 N13A -94.8(6) . . . . ?
N3A C3A C4A N8A 169.3(6) . . . . ?
N3A C3A C4A N11A -12.8(8) . . . . ?
N4A N5A N6A N7A 0.7(6) . . . . ?
N4A C1A C2A N1A 162.2(5) . . . . ?
N4A C1A C2A C3A -16.9(10) . . . . ?
N5A N4A C1A N7A 0.5(6) . . . . ?
N5A N4A C1A C2A -179.1(5) . . . . ?
N5A N6A N7A C1A -0.4(6) . . . . ?
N6A N7A C1A N4A -0.1(6) . . . . ?
N6A N7A C1A C2A 179.5(5) . . . . ?
N7A C1A C2A N1A -17.4(8) . . . . ?
N7A C1A C2A C3A 163.5(6) . . . . ?
N8A N9A N10A N11A -1.4(7) . . . . ?
N9A N8A C4A N11A -0.9(7) . . . . ?
N9A N8A C4A C3A 177.2(5) . . . . ?
N9A N10A N11A C4A 0.9(6) . . . . ?
N10A N11A C4A N8A 0.0(6) . . . . ?
N10A N11A C4A C3A -178.2(5) . . . . ?
C1A N4A N5A N6A -0.7(6) . . . . ?
C1A C2A C3A N3A 177.8(6) . . . . ?
C1A C2A C3A C4A 0.4(11) . . . . ?
C2A N1A N2A N3A -0.1(6) . . . . ?
C2A N1A N2A C013 170.2(5) . . . . ?
C2A C3A C4A N8A -13.5(10) . . . . ?
C2A C3A C4A N11A 164.4(6) . . . . ?
C4A N8A N9A N10A 1.4(7) . . . . ?
C013 N2A N3A C3A -171.0(5) . . . . ?
O1B N13B C01E N2B -4.6(7) . . . . ?
O1B N13B C01E N12B -179.8(5) . . . . ?
O2B N13B C01E N2B 175.3(5) . . . . ?
O2B N13B C01E N12B 0.1(8) . . . . ?
O3B N12B C01E N2B -178.4(5) . . . . ?
O3B N12B C01E N13B -3.1(8) . . . . ?
O4B N12B C01E N2B 1.8(7) . . . . ?
O4B N12B C01E N13B 177.1(5) . . . . ?
N1B N2B N3B C3B -2.0(6) . . . . ?
N1B N2B C01E N12B -90.4(6) . . . . ?
N1B N2B C01E N13B 94.1(6) . . . . ?
N1B C2B C3B N3B 0.9(6) . . . . ?
N1B C2B C3B C4B -176.3(6) . . . . ?
N2B N1B C2B C1B 179.8(5) . . . . ?
N2B N1B C2B C3B -2.0(6) . . . . ?
N2B N3B C3B C2B 0.6(6) . . . . ?
N2B N3B C3B C4B 178.2(5) . . . . ?
N3B N2B C01E N12B 77.9(7) . . . . ?
N3B N2B C01E N13B -97.7(6) . . . . ?
N3B C3B C4B N8B 19.6(8) . . . . ?
N3B C3B C4B N11B -158.1(5) . . . . ?
N4B N5B N6B N7B -1.9(7) . . . . ?
N4B C1B C2B N1B 14.2(8) . . . . ?
N4B C1B C2B C3B -163.5(6) . . . . ?
N5B N4B C1B N7B -1.4(7) . . . . ?
N5B N4B C1B C2B 177.4(5) . . . . ?
N5B N6B N7B C1B 1.0(7) . . . . ?
N6B N7B C1B N4B 0.3(7) . . . . ?
N6B N7B C1B C2B -178.4(6) . . . . ?
N7B C1B C2B N1B -167.1(6) . . . . ?
N7B C1B C2B C3B 15.2(11) . . . . ?
N8B N9B N10B N11B 1.1(6) . . . . ?
N9B N8B C4B N11B -0.9(6) . . . . ?
N9B N8B C4B C3B -178.9(5) . . . . ?
N9B N10B N11B C4B -1.6(6) . . . . ?
N10B N11B C4B N8B 1.5(6) . . . . ?
N10B N11B C4B C3B 179.4(5) . . . . ?
C1B N4B N5B N6B 2.0(6) . . . . ?
C1B C2B C3B N3B 178.8(6) . . . . ?
C1B C2B C3B C4B 1.6(11) . . . . ?
C01E N2B N3B C3B -170.9(5) . . . . ?
C2B N1B N2B N3B 2.5(6) . . . . ?
C2B N1B N2B C01E 171.5(5) . . . . ?
C2B C3B C4B N8B -163.5(6) . . . . ?
C2B C3B C4B N11B 18.8(10) . . . . ?
C4B N8B N9B N10B -0.1(6) . . . . ?

_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 A55b
_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.888
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(6)
2 0.4(6)

