# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_js120c
_database_code_depnum_ccdc_archive 'CCDC 2271444'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2025-01-02 downloaded from the CCDC.
;
_audit_creation_date             2020-01-22
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 N14 O8, 2(H2 O)'
_chemical_formula_sum            'C8 H12 N14 O10'
_chemical_formula_weight         464.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.5645(3)
_cell_length_b                   20.8181(3)
_cell_length_c                   4.61560(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1687.74(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.86
_cell_measurement_theta_min      3.29
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.559
_exptl_absorpt_coefficient_mu    1.467
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.8676.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.1720
0.00 0.00 -1.00 0.2240
0.00 -1.00 0.00 0.0530
0.00 1.00 0.00 0.0030
1.00 -1.00 0.00 0.0200
-1.00 1.00 0.00 0.0350
1.00 -1.00 1.00 0.1520

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.059
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  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  0.0577
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            14029
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.084
_diffrn_reflns_theta_min         3.292
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                2777
_reflns_number_total             3086
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1049 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.022
_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)+(0.0604P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0958
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O2S(H2SA,H2SB)
;
_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 0.92865(16) 0.80992(13) 1.0111(7) 0.0345(7) Uani 1 1 d . . . . .
O2 O 0.87229(15) 0.90210(12) 0.9622(7) 0.0290(6) Uani 1 1 d . . . . .
O3 O 0.54805(17) 0.73727(13) -0.3731(8) 0.0355(7) Uani 1 1 d . . . . .
O4 O 0.52676(15) 0.83220(14) -0.5480(7) 0.0333(7) Uani 1 1 d . . . . .
O5 O 0.75165(13) 0.65461(11) 0.0982(7) 0.0218(5) Uani 1 1 d . . . . .
H5 H 0.766(4) 0.709(3) 0.258(16) 0.08(2) Uiso 1 1 d . . . . .
O6 O 0.79949(15) 0.49851(12) 0.7953(6) 0.0258(6) Uani 1 1 d . . . . .
O7 O 0.52066(15) 0.53570(12) 0.8463(6) 0.0267(6) Uani 1 1 d . . . . .
O8 O 0.49648(13) 0.59945(12) 0.4892(6) 0.0260(6) Uani 1 1 d . . . . .
N1 N 0.78099(16) 0.75550(14) 0.3888(7) 0.0223(6) Uani 1 1 d . . . . .
N2 N 0.83486(16) 0.75851(14) 0.5974(8) 0.0235(6) Uani 1 1 d . . . . .
N3 N 0.78351(16) 0.85757(13) 0.5316(7) 0.0205(6) Uani 1 1 d . . . . .
N4 N 0.88197(17) 0.84579(14) 0.8977(7) 0.0239(7) Uani 1 1 d . . . . .
N5 N 0.66870(16) 0.88895(14) 0.0761(7) 0.0220(6) Uani 1 1 d . . . . .
H5A H 0.684(3) 0.928(2) 0.156(15) 0.058(17) Uiso 1 1 d . . . . .
N6 N 0.61484(16) 0.88479(14) -0.1288(7) 0.0229(6) Uani 1 1 d . . . . .
N7 N 0.65559(16) 0.78483(13) -0.0099(7) 0.0210(6) Uani 1 1 d . . . . .
N8 N 0.55739(16) 0.79498(15) -0.3791(8) 0.0254(7) Uani 1 1 d . . . . .
N9 N 0.72420(17) 0.61430(13) 0.3068(7) 0.0192(6) Uani 1 1 d . . . . .
N10 N 0.74810(16) 0.53333(13) 0.6438(7) 0.0214(6) Uani 1 1 d . . . . .
N11 N 0.84713(17) 0.58173(15) 0.3950(8) 0.0244(7) Uani 1 1 d . . . . .
H11A H 0.875(3) 0.561(2) 0.494(12) 0.034(13) Uiso 1 1 d . . . . .
H11B H 0.860(3) 0.608(2) 0.267(12) 0.033(14) Uiso 1 1 d . . . . .
N12 N 0.65762(19) 0.49037(14) 0.9327(7) 0.0216(6) Uani 1 1 d . . . . .
H12A H 0.616(3) 0.483(2) 0.975(11) 0.027(12) Uiso 1 1 d . . . . .
H12B H 0.693(3) 0.463(2) 0.996(11) 0.029(11) Uiso 1 1 d . . . . .
N13 N 0.54199(16) 0.56834(13) 0.6387(7) 0.0221(7) Uani 1 1 d . . . . .
N14 N 0.60659(18) 0.65081(14) 0.1877(7) 0.0217(6) Uani 1 1 d . . . . .
H14A H 0.625(2) 0.680(2) 0.077(11) 0.024(11) Uiso 1 1 d . . . . .
H14B H 0.553(3) 0.650(2) 0.229(14) 0.055(17) Uiso 1 1 d . . . . .
C1 C 0.83325(18) 0.81980(17) 0.6720(8) 0.0207(7) Uani 1 1 d . . . . .
C2 C 0.75155(18) 0.81466(16) 0.3562(8) 0.0193(7) Uani 1 1 d . . . . .
C3 C 0.69257(19) 0.82926(15) 0.1450(8) 0.0197(7) Uani 1 1 d . . . . .
C4 C 0.61029(19) 0.82210(17) -0.1698(8) 0.0208(7) Uani 1 1 d . . . . .
C5 C 0.77545(19) 0.57644(15) 0.4492(8) 0.0210(7) Uani 1 1 d . . . . .
C6 C 0.6730(2) 0.53011(16) 0.7220(8) 0.0209(7) Uani 1 1 d . . . . .
C7 C 0.62068(19) 0.57019(16) 0.5701(8) 0.0205(7) Uani 1 1 d . . . . .
C8 C 0.64710(19) 0.61276(15) 0.3509(8) 0.0190(7) Uani 1 1 d . . . . .
O1S O 0.92031(16) 0.66342(15) 0.9902(8) 0.0334(6) Uani 1 1 d . . . . .
H1SA H 0.902(3) 0.690(2) 0.878(13) 0.038(14) Uiso 1 1 d . . . . .
H1SB H 0.951(4) 0.689(4) 1.13(3) 0.13(3) Uiso 1 1 d . . . . .
O2S O 0.98347(16) 0.53204(13) 0.6242(8) 0.0335(7) Uani 1 1 d G . . . .
H2SA H 1.004931 0.568806 0.660648 0.050 Uiso 1 1 d G U . . .
H2SB H 0.987467 0.510638 0.785341 0.050 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.226(4) . ?
O2 N4 1.221(4) . ?
O3 N8 1.213(4) . ?
O4 N8 1.224(4) . ?
O5 H5 1.38(7) . ?
O5 N9 1.365(4) . ?
O6 N10 1.353(4) . ?
O7 N13 1.233(4) . ?
O8 N13 1.239(4) . ?
N1 H5 1.17(7) . ?
N1 N2 1.352(4) . ?
N1 C2 1.344(4) . ?
N2 C1 1.322(5) . ?
N3 C1 1.342(5) . ?
N3 C2 1.330(5) . ?
N4 C1 1.453(5) . ?
N5 H5A 0.93(6) . ?
N5 N6 1.340(4) . ?
N5 C3 1.350(4) . ?
N6 C4 1.321(5) . ?
N7 C3 1.337(5) . ?
N7 C4 1.334(5) . ?
N8 C4 1.454(5) . ?
N9 C5 1.365(5) . ?
N9 C8 1.370(5) . ?
N10 C5 1.357(5) . ?
N10 C6 1.369(5) . ?
N11 H11A 0.79(5) . ?
N11 H11B 0.83(5) . ?
N11 C5 1.288(5) . ?
N12 H12A 0.78(5) . ?
N12 H12B 0.90(5) . ?
N12 C6 1.305(5) . ?
N13 C7 1.418(5) . ?
N14 H14A 0.86(5) . ?
N14 H14B 0.97(6) . ?
N14 C8 1.304(5) . ?
C2 C3 1.454(5) . ?
C6 C7 1.426(5) . ?
C7 C8 1.423(5) . ?
O1S H1SA 0.82(6) . ?
O1S H1SB 1.00(11) . ?
O2S H2SA 0.8697 . ?
O2S H2SB 0.8698 . ?

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
N9 O5 H5 101(3) . . ?
N2 N1 H5 125(3) . . ?
C2 N1 H5 127(3) . . ?
C2 N1 N2 107.9(3) . . ?
C1 N2 N1 102.4(3) . . ?
C2 N3 C1 100.1(3) . . ?
O1 N4 C1 118.2(3) . . ?
O2 N4 O1 125.0(3) . . ?
O2 N4 C1 116.8(3) . . ?
N6 N5 H5A 123(4) . . ?
N6 N5 C3 109.0(3) . . ?
C3 N5 H5A 128(4) . . ?
C4 N6 N5 102.0(3) . . ?
C4 N7 C3 100.6(3) . . ?
O3 N8 O4 125.6(3) . . ?
O3 N8 C4 117.1(3) . . ?
O4 N8 C4 117.3(3) . . ?
O5 N9 C8 117.9(3) . . ?
C5 N9 O5 117.5(3) . . ?
C5 N9 C8 124.5(3) . . ?
O6 N10 C5 117.4(3) . . ?
O6 N10 C6 118.7(3) . . ?
C5 N10 C6 123.2(3) . . ?
H11A N11 H11B 127(5) . . ?
C5 N11 H11A 116(4) . . ?
C5 N11 H11B 117(3) . . ?
H12A N12 H12B 117(4) . . ?
C6 N12 H12A 121(4) . . ?
C6 N12 H12B 120(3) . . ?
O7 N13 O8 121.7(3) . . ?
O7 N13 C7 119.0(3) . . ?
O8 N13 C7 119.4(3) . . ?
H14A N14 H14B 119(4) . . ?
C8 N14 H14A 125(3) . . ?
C8 N14 H14B 115(3) . . ?
N2 C1 N3 117.0(3) . . ?
N2 C1 N4 122.3(3) . . ?
N3 C1 N4 120.8(3) . . ?
N1 C2 C3 122.7(3) . . ?
N3 C2 N1 112.6(3) . . ?
N3 C2 C3 124.6(3) . . ?
N5 C3 C2 124.9(3) . . ?
N7 C3 N5 111.1(3) . . ?
N7 C3 C2 124.0(3) . . ?
N6 C4 N7 117.3(3) . . ?
N6 C4 N8 121.2(3) . . ?
N7 C4 N8 121.5(3) . . ?
N10 C5 N9 117.8(3) . . ?
N11 C5 N9 120.1(3) . . ?
N11 C5 N10 122.1(3) . . ?
N10 C6 C7 117.6(3) . . ?
N12 C6 N10 115.3(3) . . ?
N12 C6 C7 127.1(3) . . ?
N13 C7 C6 120.2(3) . . ?
N13 C7 C8 119.6(3) . . ?
C8 C7 C6 120.3(3) . . ?
N9 C8 C7 116.3(3) . . ?
N14 C8 N9 116.1(3) . . ?
N14 C8 C7 127.7(3) . . ?
H1SA O1S H1SB 105(6) . . ?
H2SA O2S H2SB 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
N5 H5A O6 0.93(6) 1.63(6) 2.557(4) 173(5) 4_654 yes
N11 H11A O2S 0.79(5) 2.09(5) 2.815(4) 152(5) . yes
N11 H11B O1S 0.83(5) 2.03(5) 2.835(4) 163(5) 1_554 yes
N12 H12A O7 0.78(5) 2.09(5) 2.615(4) 125(4) . yes
N14 H14B O8 0.97(6) 1.88(6) 2.612(4) 130(5) . yes
O1S H1SB O4 1.00(11) 2.04(11) 2.837(4) 135(7) 3_567 yes
O2S H2SB O2S 0.87 1.87 2.728(3) 168.7 2_765 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N4 C1 N2 3.8(5) . . . . ?
O1 N4 C1 N3 -177.0(3) . . . . ?
O2 N4 C1 N2 -175.3(3) . . . . ?
O2 N4 C1 N3 3.9(5) . . . . ?
O3 N8 C4 N6 -168.9(3) . . . . ?
O3 N8 C4 N7 10.4(5) . . . . ?
O4 N8 C4 N6 11.8(5) . . . . ?
O4 N8 C4 N7 -168.8(3) . . . . ?
O5 N9 C5 N10 -175.9(3) . . . . ?
O5 N9 C5 N11 3.3(5) . . . . ?
O5 N9 C8 N14 -0.3(4) . . . . ?
O5 N9 C8 C7 -180.0(3) . . . . ?
O6 N10 C5 N9 -176.5(3) . . . . ?
O6 N10 C5 N11 4.3(5) . . . . ?
O6 N10 C6 N12 -3.1(5) . . . . ?
O6 N10 C6 C7 176.3(3) . . . . ?
O7 N13 C7 C6 5.9(5) . . . . ?
O7 N13 C7 C8 -173.5(3) . . . . ?
O8 N13 C7 C6 -174.1(3) . . . . ?
O8 N13 C7 C8 6.6(5) . . . . ?
N1 N2 C1 N3 -0.2(4) . . . . ?
N1 N2 C1 N4 179.0(3) . . . . ?
N1 C2 C3 N5 -170.4(3) . . . . ?
N1 C2 C3 N7 8.6(5) . . . . ?
N2 N1 C2 N3 0.5(4) . . . . ?
N2 N1 C2 C3 179.0(3) . . . . ?
N3 C2 C3 N5 7.9(6) . . . . ?
N3 C2 C3 N7 -173.1(3) . . . . ?
N5 N6 C4 N7 0.5(4) . . . . ?
N5 N6 C4 N8 179.9(3) . . . . ?
N6 N5 C3 N7 -0.1(4) . . . . ?
N6 N5 C3 C2 179.0(3) . . . . ?
N10 C6 C7 N13 179.1(3) . . . . ?
N10 C6 C7 C8 -1.5(5) . . . . ?
N12 C6 C7 N13 -1.5(5) . . . . ?
N12 C6 C7 C8 177.8(3) . . . . ?
N13 C7 C8 N9 176.8(3) . . . . ?
N13 C7 C8 N14 -2.9(5) . . . . ?
C1 N3 C2 N1 -0.6(4) . . . . ?
C1 N3 C2 C3 -179.0(3) . . . . ?
C2 N1 N2 C1 -0.2(4) . . . . ?
C2 N3 C1 N2 0.4(4) . . . . ?
C2 N3 C1 N4 -178.8(3) . . . . ?
C3 N5 N6 C4 -0.2(4) . . . . ?
C3 N7 C4 N6 -0.6(4) . . . . ?
C3 N7 C4 N8 -179.9(3) . . . . ?
C4 N7 C3 N5 0.4(4) . . . . ?
C4 N7 C3 C2 -178.7(3) . . . . ?
C5 N9 C8 N14 -177.6(3) . . . . ?
C5 N9 C8 C7 2.7(5) . . . . ?
C5 N10 C6 N12 -173.4(3) . . . . ?
C5 N10 C6 C7 6.1(5) . . . . ?
C6 N10 C5 N9 -6.1(5) . . . . ?
C6 N10 C5 N11 174.7(4) . . . . ?
C6 C7 C8 N9 -2.6(5) . . . . ?
C6 C7 C8 N14 177.8(3) . . . . ?
C8 N9 C5 N10 1.4(5) . . . . ?
C8 N9 C5 N11 -179.3(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JC050
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_js1022h
_database_code_depnum_ccdc_archive 'CCDC 2271445'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2025-01-02 downloaded from the CCDC.
;
_audit_creation_date             2022-11-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H6 N6 O4, 5(H2 O), 2(C3 H3 N5 O4)'
_chemical_formula_sum            'C10 H22 N16 O17'
_chemical_formula_weight         638.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H12N10O6
_chemical_oxdiff_usercomment     JC2209
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.53246(13)
_cell_length_b                   12.9761(3)
_cell_length_c                   15.8032(3)
_cell_angle_alpha                113.661(2)
_cell_angle_beta                 93.6318(19)
_cell_angle_gamma                94.1291(17)
_cell_volume                     1217.52(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8731
_cell_measurement_temperature    144(2)
_cell_measurement_theta_max      79.1600
_cell_measurement_theta_min      3.0720
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.584
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0160
0 0 1 0.0256
-4 5 -1 0.0990
0 -8 3 0.0964
4 1 -1 0.2111
1 8 -3 0.1297
-2 8 -5 0.0801

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.042
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0003 -0.0007 -0.9995 -0.0756 0.0753 0.0081
0.0003 0.0007 0.9995 0.0756 -0.0753 -0.0081
-3.5514 5.0910 -1.4506 0.6547 0.5598 0.5080
-0.1993 -8.3156 3.1829 -0.6649 -0.5670 0.4862
4.1493 1.0792 -0.9722 -0.1917 -0.1651 -0.9675
0.9769 7.9834 -3.1622 0.5854 0.4989 -0.6391
-2.0270 7.5841 -4.5556 0.6078 0.7921 0.0565

_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16678
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.341
_diffrn_reflns_theta_min         3.069
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      144(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00 103.00   0.50    0.06    --   47.44-146.00 107.00  110
  2  ω     99.00 124.00   0.50    0.25    --  113.25-146.00 107.00   50
  3  ω     62.00  91.00   0.50    0.06    --   47.44-125.00 -85.00   58
  4  ω     79.00 108.00   0.50    0.25    --  113.25-125.00-180.00   58
  5  ω     52.00  77.00   0.50    0.25    --  113.25-125.00 -85.00   50
  6  ω     71.00 104.00   0.50    0.25    --  113.25 -94.00 -90.00   66
  7  ω     70.00 100.00   0.50    0.25    --  113.25 -94.00   0.00   60
  8  ω     48.00  74.00   0.50    0.25    --  113.25-106.00 103.19   52
  9  ω     80.00 105.00   0.50    0.25    --  113.25-106.00 103.19   50
 10  ω     46.00 104.00   0.50    0.25    --  113.25-125.00  30.00  116
 11  ω     71.00 104.00   0.50    0.25    --  113.25 -94.00 -60.00   66
 12  ω     77.00 102.00   0.50    0.25    --  113.25 -94.00-120.00   50
 13  ω     42.00  68.00   0.50    0.25    --  113.25 -94.00 -90.00   52
 14  ω     47.00 101.00   0.50    0.25    --  113.25 -94.00-150.00  108
 15  ω     74.00 102.00   0.50    0.25    --  113.25 -94.00-180.00   56
 16  ω     42.00  67.00   0.50    0.25    --  113.25 -94.00-180.00   50
 17  ω     42.00  68.00   0.50    0.25    --  113.25 -94.00 -60.00   52
 18  ω     78.00 103.00   0.50    0.25    --  113.25 -94.00  30.00   50
 19  ω     46.00  71.00   0.50    0.25    --  113.25 -94.00  30.00   50
 20  ω     42.00  67.00   0.50    0.25    --  113.25 -94.00  90.00   50
 21  ω     78.00 103.00   0.50    0.25    --  113.25 -94.00  90.00   50
 22  ω     79.00 104.00   0.50    0.25    --  113.25 -94.00  60.00   50
 23  ω     47.00  72.00   0.50    0.25    --  113.25 -77.00  30.00   50
 24  ω     42.00  70.00   0.50    0.25    --  113.25 -77.00 120.00   56
 25  ω     42.00  69.00   0.50    0.25    --  113.25 -61.00 150.00   54
 26  ω     80.00 105.00   0.50    0.25    --  113.25 -77.00 120.00   50
 27  ω     43.00  69.00   0.50    0.25    --  113.25 -61.00 -60.00   52
 28  ω     42.00  67.00   0.50    0.25    --  113.25 -61.00-120.00   50
 29  ω     43.00  68.00   0.50    0.25    --  113.25 -61.00-150.00   50
 30  ω     42.00  67.00   0.50    0.25    --  113.25 -61.00 -90.00   50
 31  ω     43.00  69.00   0.50    0.25    --  113.25 -61.00 -30.00   52
 32  ω     43.00  69.00   0.50    0.25    --  113.25 -61.00  60.00   52
 33  ω     42.00  67.00   0.50    0.25    --  113.25 -61.00  90.00   50
 34  ω     43.00  68.00   0.50    0.25    --  113.25 -61.00 120.00   50
 35  ω    127.00 178.00   0.50    0.25    --  113.25  77.00 150.00  102
 36  ω    152.00 178.00   0.50    0.25    --  113.25  77.00  90.00   52
 37  ω    122.00 170.00   0.50    0.25    --  113.25  45.00  60.00   96
 38  ω    135.00 178.00   0.50    0.25    --  113.25  45.00 120.00   86
 39  ω    122.00 170.00   0.50    0.25    --  113.25  45.00   0.00   96
 40  ω    130.00 165.00   0.50    0.25    --  113.25  77.00 -30.00   70
 41  ω    124.00 178.00   0.50    0.25    --  113.25  45.00 -60.00  108
 42  ω    126.00 160.00   0.50    0.25    --  113.25  45.00 -90.00   68
 43  ω    123.00 178.00   0.50    0.25    --  113.25  45.00-120.00  110
 44  ω    124.00 167.00   0.50    0.25    --  113.25  45.00-150.00   86
 45  ω    113.00 138.00   0.50    0.25    --  113.25 125.00-120.00   50
 46  ω    150.00 176.00   0.50    0.25    --  113.25 125.00-120.00   52
 47  ω     97.00 140.00   0.50    0.25    --  113.25 125.00  -7.00   86
 48  ω     92.00 125.00   0.50    0.25    --  113.25 146.00 159.00   66
 49  ω    -26.00  41.00   0.50    0.06    --   47.44 -37.00   0.00  134
 50  ω    -27.00  25.00   0.50    0.06    --   47.44 -19.00 120.00  104
 51  ω    -27.00  24.00   0.50    0.06    --   47.44 -19.00-120.00  102
 52  ω    -14.00  11.00   0.50    0.06    --   47.44 -19.00-150.00   50
 53  ω    -11.00  23.00   0.50    0.06    --   47.44 -19.00-180.00   68
 54  ω    -24.00  11.00   0.50    0.06    --  -47.44  19.00-150.00   70
 55  ω    -73.00 -48.00   0.50    0.06    --  -47.44 125.00  -7.00   50
 56  ω    -86.00 -61.00   0.50    0.06    --  -47.44 146.00 159.00   50
 57  ω    -86.00 -61.00   0.50    0.25    --  -91.75 146.00 159.00   50
 58  ω    -42.00  23.00   0.50    0.06    --  -47.44  37.00 -90.00  130
 59  ω   -144.00 -93.00   0.50    0.25    --  -91.75 -30.00 -30.00  102
 60  ω   -163.00-125.00   0.50    0.25    --  -91.75 -45.00  30.00   76
 61  ω   -159.00-133.00   0.50    0.25    --  -91.75 -77.00   0.00   52
 62  ω   -154.00-129.00   0.50    0.25    --  -91.75 -77.00 150.00   50
 63  ω   -103.00 -61.00   0.50    0.06    --  -47.44-146.00 107.00   84
 64  ω   -129.00-104.00   0.50    0.25    --  -91.75-146.00 107.00   50
 65  ω   -119.00 -93.00   0.50    0.25    --  -91.75-125.00 -85.00   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      -0.0571644000
_diffrn_orient_matrix_UB_12      0.1102371000
_diffrn_orient_matrix_UB_13      0.0755315000
_diffrn_orient_matrix_UB_21      -0.0681080000
_diffrn_orient_matrix_UB_22      0.0409795000
_diffrn_orient_matrix_UB_23      -0.0753389000
_diffrn_orient_matrix_UB_31      -0.2203994000
_diffrn_orient_matrix_UB_32      -0.0562375000
_diffrn_orient_matrix_UB_33      -0.0079565000
_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                4559
_reflns_number_total             5052
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.116
_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)+(0.1026P)²+0.3745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1598
_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB), O5W(H5WA,H5WB)
2.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N12(H12)
2.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N9(H9A,H9B), N14(H14A,H14B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39606(18) 0.22258(11) 0.64403(9) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.09430(18) 0.05345(10) 0.33978(9) 0.0205(3) Uani 1 1 d . . . . .
O3 O 0.1553(2) 0.46743(12) 0.41686(10) 0.0281(3) Uani 1 1 d . . . . .
O4 O 0.3162(2) 0.54375(11) 0.55511(10) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.3116(2) 0.23531(12) 0.56844(10) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.1691(2) 0.15020(12) 0.41399(10) 0.0171(3) Uani 1 1 d . . . . .
N3 N 0.4152(2) 0.42171(12) 0.64606(11) 0.0214(3) Uani 1 1 d . . . . .
H3A H 0.463412 0.405497 0.692028 0.026 Uiso 1 1 calc R U . . .
H3B H 0.428354 0.492115 0.651471 0.026 Uiso 1 1 calc R U . . .
N4 N 0.2525(2) 0.04163(12) 0.49478(11) 0.0196(3) Uani 1 1 d . . . . .
H4A H 0.301564 0.036793 0.546063 0.024 Uiso 1 1 calc R U . . .
H4B H 0.208767 -0.020265 0.445171 0.024 Uiso 1 1 calc R U . . .
N5 N 0.0662(2) 0.24680(13) 0.33050(11) 0.0209(3) Uani 1 1 d . . . . .
H5A H 0.021825 0.180719 0.285442 0.025 Uiso 1 1 calc R U . . .
H5B H 0.051623 0.309428 0.322730 0.025 Uiso 1 1 calc R U . . .
N6 N 0.2356(2) 0.45812(12) 0.48641(11) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.2445(2) 0.14015(14) 0.49230(12) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.1541(2) 0.25194(14) 0.40915(12) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.2362(2) 0.35112(14) 0.48832(12) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.3235(2) 0.34075(14) 0.56931(12) 0.0176(3) Uani 1 1 d . . . . .
O1W O 0.1260(2) 0.25228(11) 0.76305(9) 0.0253(3) Uani 1 1 d G . . . .
H1WA H 0.222743 0.238846 0.725760 0.038 Uiso 1 1 d G U . . .
H1WB H 0.120415 0.196416 0.780274 0.038 Uiso 1 1 d G U . . .
O2W O 0.8015(2) 0.19106(11) 0.62217(10) 0.0267(3) Uani 1 1 d G . . . .
H2WA H 0.886070 0.218021 0.672665 0.040 Uiso 1 1 d G U . . .
H2WB H 0.682052 0.210212 0.640944 0.040 Uiso 1 1 d G U . . .
O3W O 0.7031(2) 0.24619(12) 0.47296(11) 0.0311(3) Uani 1 1 d G . . . .
H3WA H 0.762522 0.257555 0.527272 0.047 Uiso 1 1 d G U . . .
H3WB H 0.716262 0.312394 0.471021 0.047 Uiso 1 1 d G U . . .
O4W O 0.68510(18) 0.02578(11) 0.35359(10) 0.0234(3) Uani 1 1 d G . . . .
H4WA H 0.813530 0.022038 0.342154 0.035 Uiso 1 1 d G U . . .
H4WB H 0.675228 0.097716 0.383315 0.035 Uiso 1 1 d G U . . .
O5 O 0.0251(3) 0.50798(15) 0.74738(11) 0.0390(4) Uani 1 1 d . . . . .
O6 O 0.0727(2) 0.69055(14) 0.83132(12) 0.0361(4) Uani 1 1 d . . . . .
O7 O 0.3815(2) 0.53464(11) 1.15374(10) 0.0254(3) Uani 1 1 d . . . . .
O8 O 0.3619(2) 0.70992(12) 1.17493(11) 0.0337(3) Uani 1 1 d . . . . .
N7 N 0.1677(2) 0.46518(13) 0.89225(11) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.135538 0.403494 0.841020 0.025 Uiso 1 1 calc R U . . .
N8 N 0.2383(2) 0.46538(12) 0.97196(10) 0.0186(3) Uani 1 1 d . . . . .
N9 N 0.2177(2) 0.76255(13) 1.02781(12) 0.0257(3) Uani 1 1 d . . . . .
H9A H 0.177376 0.798562 0.993963 0.031 Uiso 1 1 calc R U . . .
H9B H 0.261503 0.800758 1.086931 0.031 Uiso 1 1 calc R U . . .
N10 N 0.0778(2) 0.59050(15) 0.82060(12) 0.0277(4) Uani 1 1 d . . . . .
N11 N 0.3404(2) 0.60749(12) 1.12512(11) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.1500(2) 0.57199(16) 0.89826(13) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.2125(2) 0.64957(15) 0.98934(13) 0.0198(3) Uani 1 1 d . . . . .
C7 C 0.2661(2) 0.57531(14) 1.03105(12) 0.0180(3) Uani 1 1 d . . . . .
O5W O 0.36493(19) -0.04247(11) 0.22235(9) 0.0225(3) Uani 1 1 d G . . . .
H5WA H 0.480487 -0.029443 0.257265 0.034 Uiso 1 1 d G U . . .
H5WB H 0.276966 -0.008603 0.260684 0.034 Uiso 1 1 d G U . . .
O9 O 0.5268(2) 0.22436(12) 0.27776(10) 0.0304(3) Uani 1 1 d . . . . .
O10 O 0.4811(2) 0.35354(11) 0.22399(10) 0.0297(3) Uani 1 1 d . . . . .
O11 O 0.1208(2) -0.07076(11) -0.15016(10) 0.0296(3) Uani 1 1 d . . . . .
O12 O 0.1514(2) 0.10359(12) -0.13753(10) 0.0311(3) Uani 1 1 d . . . . .
N12 N 0.3518(2) 0.05999(12) 0.11417(10) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.384550 0.032837 0.155507 0.023 Uiso 1 1 calc R U . . .
N13 N 0.2694(2) -0.00190(12) 0.02889(10) 0.0191(3) Uani 1 1 d . . . . .
N14 N 0.3088(2) 0.28038(13) 0.03585(12) 0.0237(3) Uani 1 1 d . . . . .
H14A H 0.355423 0.346150 0.080818 0.028 Uiso 1 1 calc R U . . .
H14B H 0.260605 0.276900 -0.018608 0.028 Uiso 1 1 calc R U . . .
N15 N 0.4681(2) 0.25364(13) 0.21574(11) 0.0216(3) Uani 1 1 d . . . . .
N16 N 0.1682(2) 0.03151(13) -0.10487(11) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.3800(2) 0.17134(14) 0.13023(12) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.3113(2) 0.18541(14) 0.05033(12) 0.0183(3) Uani 1 1 d . . . . .
C10 C 0.2455(2) 0.07146(14) -0.01105(12) 0.0181(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3588(18) . ?
O2 N2 1.3592(18) . ?
O3 N6 1.241(2) . ?
O4 N6 1.251(2) . ?
N1 C1 1.352(2) . ?
N1 C4 1.359(2) . ?
N2 C1 1.361(2) . ?
N2 C2 1.363(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C4 1.315(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C1 1.299(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C2 1.310(2) . ?
N6 C3 1.401(2) . ?
C2 C3 1.426(2) . ?
C3 C4 1.428(2) . ?
O1W H1WA 0.8704 . ?
O1W H1WB 0.8698 . ?
O2W H2WA 0.8698 . ?
O2W H2WB 0.8699 . ?
O3W H3WA 0.8701 . ?
O3W H3WB 0.8701 . ?
O4W H4WA 0.8700 . ?
O4W H4WB 0.8699 . ?
O5 N10 1.227(2) . ?
O6 N10 1.243(2) . ?
O7 N11 1.239(2) . ?
O8 N11 1.235(2) . ?
N7 H7 0.8800 . ?
N7 N8 1.313(2) . ?
N7 C5 1.364(2) . ?
N8 C7 1.346(2) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N9 C6 1.340(2) . ?
N10 C5 1.402(2) . ?
N11 C7 1.415(2) . ?
C5 C6 1.398(3) . ?
C6 C7 1.419(2) . ?
O5W H5WA 0.8700 . ?
O5W H5WB 0.8702 . ?
O9 N15 1.235(2) . ?
O10 N15 1.246(2) . ?
O11 N16 1.233(2) . ?
O12 N16 1.244(2) . ?
N12 H12 0.8800 . ?
N12 N13 1.315(2) . ?
N12 C8 1.359(2) . ?
N13 C10 1.349(2) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N14 C9 1.342(2) . ?
N15 C8 1.397(2) . ?
N16 C10 1.404(2) . ?
C8 C9 1.398(2) . ?
C9 C10 1.420(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
O1 N1 C4 118.51(14) . . ?
C1 N1 O1 117.35(14) . . ?
C1 N1 C4 123.57(15) . . ?
O2 N2 C1 117.39(13) . . ?
O2 N2 C2 119.40(14) . . ?
C1 N2 C2 123.08(14) . . ?
H3A N3 H3B 120.0 . . ?
C4 N3 H3A 120.0 . . ?
C4 N3 H3B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
O3 N6 O4 120.47(15) . . ?
O3 N6 C3 119.95(15) . . ?
O4 N6 C3 119.58(15) . . ?
N1 C1 N2 118.65(15) . . ?
N4 C1 N1 120.08(15) . . ?
N4 C1 N2 121.28(15) . . ?
N2 C2 C3 117.46(15) . . ?
N5 C2 N2 115.31(15) . . ?
N5 C2 C3 127.23(16) . . ?
N6 C3 C2 120.48(15) . . ?
N6 C3 C4 119.94(15) . . ?
C2 C3 C4 119.57(15) . . ?
N1 C4 C3 117.19(15) . . ?
N3 C4 N1 115.07(15) . . ?
N3 C4 C3 127.74(16) . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?
H3WA O3W H3WB 104.5 . . ?
H4WA O4W H4WB 104.5 . . ?
N8 N7 H7 124.0 . . ?
N8 N7 C5 111.98(15) . . ?
C5 N7 H7 124.0 . . ?
N7 N8 C7 104.84(14) . . ?
H9A N9 H9B 120.0 . . ?
C6 N9 H9A 120.0 . . ?
C6 N9 H9B 120.0 . . ?
O5 N10 O6 124.69(18) . . ?
O5 N10 C5 118.37(17) . . ?
O6 N10 C5 116.94(17) . . ?
O7 N11 C7 120.22(15) . . ?
O8 N11 O7 123.26(16) . . ?
O8 N11 C7 116.52(15) . . ?
N7 C5 N10 121.06(17) . . ?
N7 C5 C6 109.01(15) . . ?
C6 C5 N10 129.92(17) . . ?
N9 C6 C5 130.16(17) . . ?
N9 C6 C7 129.21(18) . . ?
C5 C6 C7 100.63(15) . . ?
N8 C7 N11 120.40(15) . . ?
N8 C7 C6 113.54(16) . . ?
N11 C7 C6 126.06(16) . . ?
H5WA O5W H5WB 104.5 . . ?
N13 N12 H12 124.4 . . ?
N13 N12 C8 111.24(14) . . ?
C8 N12 H12 124.4 . . ?
N12 N13 C10 105.53(14) . . ?
H14A N14 H14B 120.0 . . ?
C9 N14 H14A 120.0 . . ?
C9 N14 H14B 120.0 . . ?
O9 N15 O10 124.18(16) . . ?
O9 N15 C8 119.25(15) . . ?
O10 N15 C8 116.56(15) . . ?
O11 N16 O12 123.60(16) . . ?
O11 N16 C10 119.60(15) . . ?
O12 N16 C10 116.80(15) . . ?
N12 C8 N15 121.79(16) . . ?
N12 C8 C9 109.70(15) . . ?
N15 C8 C9 128.51(15) . . ?
N14 C9 C8 129.56(17) . . ?
N14 C9 C10 129.82(17) . . ?
C8 C9 C10 100.61(14) . . ?
N13 C10 N16 120.10(15) . . ?
N13 C10 C9 112.91(16) . . ?
N16 C10 C9 126.95(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3B O4 0.88 2.01 2.617(2) 124.8 . yes
N3 H3B O10 0.88 2.18 2.813(2) 128.5 2_666 yes
N4 H4A O4W 0.88 2.05 2.878(2) 156.1 2_656 yes
N4 H4B O2W 0.88 2.03 2.818(2) 148.3 2_656 yes
N5 H5A O11 0.88 2.14 2.961(2) 154.8 2 yes
N5 H5B O3 0.88 2.02 2.631(2) 125.1 . yes
N5 H5B O6 0.88 2.52 3.083(2) 122.7 2_566 yes
O1W H1WA O1 0.87 1.73 2.5951(18) 171.8 . yes
O1W H1WB O12 0.87 2.11 2.9435(19) 161.3 1_556 yes
O2W H2WA O1W 0.87 1.95 2.7968(19) 164.2 1_655 yes
O2W H2WB O1 0.87 1.89 2.7313(18) 162.7 . yes
O3W H3WA O2W 0.87 2.02 2.777(2) 144.9 . yes
O3W H3WB O4 0.87 2.09 2.9419(19) 166.4 2_666 yes
O4W H4WA O2 0.87 1.86 2.7056(17) 164.9 1_655 yes
O4W H4WB O3W 0.87 1.87 2.7103(19) 163.5 . yes
O5W H5WA O4W 0.87 1.83 2.6777(18) 164.5 . yes
O5W H5WB O2 0.87 1.78 2.6453(17) 176.8 . yes
N14 H14A O7 0.88 2.23 3.051(2) 154.3 1_554 yes
N14 H14A O10 0.88 2.32 2.857(2) 119.5 . yes
N14 H14B N8 0.88 2.52 3.007(2) 115.3 1_554 yes
N14 H14B O12 0.88 2.30 2.844(2) 119.7 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 N2 -176.63(12) . . . . ?
O1 N1 C1 N4 3.5(2) . . . . ?
O1 N1 C4 N3 -1.1(2) . . . . ?
O1 N1 C4 C3 179.02(12) . . . . ?
O2 N2 C1 N1 -177.17(12) . . . . ?
O2 N2 C1 N4 2.7(2) . . . . ?
O2 N2 C2 N5 -0.1(2) . . . . ?
O2 N2 C2 C3 -179.45(12) . . . . ?
O3 N6 C3 C2 3.0(2) . . . . ?
O3 N6 C3 C4 -178.27(14) . . . . ?
O4 N6 C3 C2 -176.98(14) . . . . ?
O4 N6 C3 C4 1.7(2) . . . . ?
N2 C2 C3 N6 176.73(13) . . . . ?
N2 C2 C3 C4 -2.0(2) . . . . ?
N5 C2 C3 N6 -2.5(2) . . . . ?
N5 C2 C3 C4 178.80(14) . . . . ?
N6 C3 C4 N1 177.25(13) . . . . ?
N6 C3 C4 N3 -2.6(2) . . . . ?
C1 N1 C4 N3 -172.16(14) . . . . ?
C1 N1 C4 C3 7.9(2) . . . . ?
C1 N2 C2 N5 -175.91(13) . . . . ?
C1 N2 C2 C3 4.8(2) . . . . ?
C2 N2 C1 N1 -1.3(2) . . . . ?
C2 N2 C1 N4 178.57(14) . . . . ?
C2 C3 C4 N1 -4.0(2) . . . . ?
C2 C3 C4 N3 176.09(15) . . . . ?
C4 N1 C1 N2 -5.4(2) . . . . ?
C4 N1 C1 N4 174.65(14) . . . . ?
O5 N10 C5 N7 2.0(2) . . . . ?
O5 N10 C5 C6 -177.69(16) . . . . ?
O6 N10 C5 N7 -177.75(15) . . . . ?
O6 N10 C5 C6 2.6(3) . . . . ?
O7 N11 C7 N8 0.4(2) . . . . ?
O7 N11 C7 C6 179.75(15) . . . . ?
O8 N11 C7 N8 179.99(15) . . . . ?
O8 N11 C7 C6 -0.6(2) . . . . ?
N7 N8 C7 N11 179.45(13) . . . . ?
N7 N8 C7 C6 0.01(18) . . . . ?
N7 C5 C6 N9 -178.60(16) . . . . ?
N7 C5 C6 C7 0.37(16) . . . . ?
N8 N7 C5 N10 179.84(14) . . . . ?
N8 N7 C5 C6 -0.42(18) . . . . ?
N9 C6 C7 N8 178.74(16) . . . . ?
N9 C6 C7 N11 -0.7(3) . . . . ?
N10 C5 C6 N9 1.1(3) . . . . ?
N10 C5 C6 C7 -179.91(16) . . . . ?
C5 N7 N8 C7 0.25(17) . . . . ?
C5 C6 C7 N8 -0.24(17) . . . . ?
C5 C6 C7 N11 -179.64(15) . . . . ?
O9 N15 C8 N12 1.8(2) . . . . ?
O9 N15 C8 C9 -177.32(15) . . . . ?
O10 N15 C8 N12 -177.88(14) . . . . ?
O10 N15 C8 C9 3.0(2) . . . . ?
O11 N16 C10 N13 0.6(2) . . . . ?
O11 N16 C10 C9 178.55(15) . . . . ?
O12 N16 C10 N13 -179.50(14) . . . . ?
O12 N16 C10 C9 -1.6(2) . . . . ?
N12 N13 C10 N16 177.26(13) . . . . ?
N12 N13 C10 C9 -0.96(18) . . . . ?
N12 C8 C9 N14 179.42(15) . . . . ?
N12 C8 C9 C10 -0.68(16) . . . . ?
N13 N12 C8 N15 -179.15(14) . . . . ?
N13 N12 C8 C9 0.16(18) . . . . ?
N14 C9 C10 N13 -179.09(15) . . . . ?
N14 C9 C10 N16 2.8(3) . . . . ?
N15 C8 C9 N14 -1.3(3) . . . . ?
N15 C8 C9 C10 178.57(16) . . . . ?
C8 N12 N13 C10 0.48(17) . . . . ?
C8 C9 C10 N13 1.01(17) . . . . ?
C8 C9 C10 N16 -177.06(15) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JC2209
_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 2.624
_oxdiff_exptl_absorpt_empirical_full_min 0.491
####################################################################### 
# 
# 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_js820e
_database_code_depnum_ccdc_archive 'CCDC 2271446'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2025-01-02 downloaded from the CCDC.
;
_audit_creation_date             2020-08-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 N8 O6, 5(H2 O), 2(C4 H7 N6 O4)'
_chemical_formula_sum            'C12 H24 N20 O19'
_chemical_formula_weight         752.51
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H8N14O10
_chemical_oxdiff_usercomment     JC065
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.96237(5)
_cell_length_b                   31.0651(3)
_cell_length_c                   7.26833(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.9177(7)
_cell_angle_gamma                90
_cell_volume                     1344.507(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12625
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.8300
_cell_measurement_theta_min      2.8300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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    1.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0042
0 1 0 0.0306
-1 0 0 0.0330
1 0 0 0.0330
1 -1 1 0.0436
-1 1 -1 0.0436
0 1 -1 0.0390
0 -1 1 0.0390

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.035
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 -1.0003 0.0000 -0.0393 0.0256 0.0163
0.0000 1.0003 -0.0000 0.0393 -0.0256 -0.0163
-0.9996 -0.0012 -0.0001 0.0990 0.0003 0.2389
0.9996 0.0012 0.0001 -0.0990 -0.0003 -0.2389
0.9995 -1.0005 1.0003 -0.2433 -0.1563 -0.1906
-0.9995 1.0005 -1.0003 0.2433 0.1563 0.1906
0.0001 1.0018 -1.0001 0.1443 0.1561 -0.0483
-0.0001 -1.0018 1.0001 -0.1443 -0.1561 0.0483

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus operating at  100 K.  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. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  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  0.0356
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17691
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.198
_diffrn_reflns_theta_min         2.845
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    109.00 135.00   0.50    1.16    --  107.11  98.00  20.00   52
  2  ω    140.00 167.00   0.50    1.16    --  107.11  98.00  20.00   54
  3  ω    126.00 177.00   0.50    1.16    --  107.11  77.00  60.00  102
  4  ω    118.00 175.00   0.50    1.16    --  107.11  37.00   0.00  114
  5  ω    -14.00  12.00   0.50    0.29    --  -47.57  19.00-150.00   52
  6  ω    -42.00 -14.00   0.50    1.16    --  -86.25  37.00-120.00   56
  7  ω    -43.00 -18.00   0.50    1.16    --  -86.25  37.00 -30.00   50
  8  ω    -43.00 -18.00   0.50    1.16    --  -86.25  37.00 120.00   50
  9  ω    -27.00  23.00   0.50    0.29    --  -47.57  19.00 150.00  100
 10  ω    -46.00 -21.00   0.50    1.16    --  -86.25  98.00  20.00   50
 11  ω   -140.00-115.00   0.50    1.16    --  -86.25 -98.00 -86.00   50
 12  ω   -152.00-127.00   0.50    1.16    --  -86.25 -57.00-180.00   50
 13  ω   -159.00-134.00   0.50    1.16    --  -86.25 -37.00 150.00   50
 14  ω     -8.00  19.00   0.50    0.29    --  -47.57  98.00  20.00   54
 15  ω     -8.00  25.00   0.50    0.29    --   47.57 -19.00 -90.00   66
 16  ω     42.00  68.00   0.50    1.16    --  107.11 -77.00 -60.00   52
 17  ω     36.00  62.00   0.50    1.16    --  107.11 -57.00 -60.00   52
 18  ω     40.00  65.00   0.50    1.16    --  107.11 -57.00-120.00   50
 19  ω     80.00 105.00   0.50    1.16    --  107.11 -77.00 -60.00   50
 20  ω     39.00  64.00   0.50    1.16    --  107.11 -57.00   0.00   50
 21  ω     37.00  64.00   0.50    1.16    --  107.11 -57.00  60.00   54
 22  ω    -24.00  41.00   0.50    0.29    --   47.57 -37.00  30.00  130
 23  ω     35.00  60.00   0.50    1.16    --  107.11 -57.00 150.00   50
 24  ω     35.00  65.00   0.50    1.16    --  107.11 -57.00 120.00   60
 25  ω     37.00  65.00   0.50    1.16    --  107.11 -57.00  90.00   56
 26  ω     39.00  90.00   0.50    1.16    --  107.11-125.00  30.00  102
 27  ω     75.00 100.00   0.50    1.16    --  107.11 -98.00 -86.00   50
 28  ω     15.00  58.00   0.50    0.29    --   47.57 -98.00 -86.00   86
 29  ω   -124.00 -99.00   0.50    1.16    --  -86.25 -98.00 -86.00   50
 30  ω    -31.00  -2.00   0.50    0.29    --  -47.45  77.00-150.00   58
 31  ω    -23.00  22.00   0.50    0.29    --  -47.45  19.00  60.00   90
 32  ω    -70.00 -34.00   0.50    0.29    --  -47.45  77.00-150.00   72
 33  ω     -7.00  20.00   0.50    0.29    --   47.45 -19.00 150.00   54
 34  ω    -27.00  21.00   0.50    0.29    --   47.45 -19.00 -30.00   96
 35  ω     42.00 116.00   0.50    0.29    --   47.45  19.00 120.00  148
 36  ω    -43.00 -18.00   0.50    1.16    --  -86.25  37.00  30.00   50
 37  ω   -148.00-119.00   0.50    1.16    --  -86.25 -37.00-180.00   58
 38  ω   -140.00-114.00   0.50    1.16    --  -86.25 -37.00 150.00   52
 39  ω   -156.00-115.00   0.50    1.16    --  -86.25 -37.00-150.00   82
 40  ω     74.00 107.00   0.50    1.16    --  107.11-125.00  90.00   66
 41  ω     40.00  66.00   0.50    1.16    --  107.11-125.00  90.00   52
 42  ω     40.00  96.00   0.50    1.16    --  107.11 -99.00-150.00  112
 43  ω    120.00 146.00   0.50    1.16    --  107.11 125.00 -60.00   52
 44  ω    148.00 178.00   0.50    1.16    --  107.11  57.00  30.00   60
 45  ω     35.00  60.00   0.50    1.16    --  107.11 -57.00 -90.00   50
 46  ω     58.00 104.00   0.50    1.16    --  107.11 -99.00 120.00   92
 47  ω    107.00 160.00   0.50    1.16    --  107.11  19.00-180.00  106
 48  ω     57.00 108.00   0.50    1.16    --  107.11-125.00 -90.00  102
 49  ω     81.00 108.00   0.50    1.16    --  107.11-125.00  60.00   54
 50  ω    153.00 178.00   0.50    1.16    --  107.11  19.00  90.00   50
 51  ω     96.00 138.00   0.50    1.16    --  107.11  19.00  90.00   84
 52  ω     44.00  92.00   0.50    1.16    --  107.11 -99.00  90.00   96
 53  ω     43.00  89.00   0.50    1.16    --  107.11 -99.00-180.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω and φ'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0990585000
_diffrn_orient_matrix_UB_12      0.0392709000
_diffrn_orient_matrix_UB_13      -0.1050092000
_diffrn_orient_matrix_UB_21      -0.0001931000
_diffrn_orient_matrix_UB_22      -0.0255615000
_diffrn_orient_matrix_UB_23      -0.1816601000
_diffrn_orient_matrix_UB_31      -0.2389739000
_diffrn_orient_matrix_UB_32      -0.0162441000
_diffrn_orient_matrix_UB_33      0.0319506000
_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         0.906
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                5230
_reflns_number_total             5420
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         5420
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+0.2282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1041
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
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(2)
 0.4(2)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 O1W-H1WA \\sim O1X-H1WA
 with sigma of 0.02
 O1W-H1WB \\sim O1X-H1WB
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(O4X) = Uanis(O4W) = Uanis(O5X) = Uanis(O5W)
Uiso(O1W) = Uiso(O1X)
5. Others
 Fixed Sof: O1W(0.5) H1WA(0.5) H1WB(0.5) O1X(0.5) H1XA(0.5) H1XB(0.5) O4W(0.5)
 H4WA(0.5) H4WB(0.5) O4X(0.5) H4XA(0.5) H4XB(0.5) O5W(0.5) H5WA(0.5) H5WB(0.5)
 O5X(0.5) H5XA(0.5) H5XB(0.5)
6.a Free rotating group:
 O1W(H1WA,H1WB), O1X(H1XA,H1XB), O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,
 H4WB), O4X(H4XA,H4XB), O5W(H5WA,H5WB), O5X(H5XA,H5XB)
6.b X=CH2 refined with riding coordinates:
 N11(H11A,H11B), N12(H12A,H12B), N13(H13A,H13B), N17(H17A,H17B), N18(H18A,
 H18B), N19(H19A,H19B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6869(4) 0.44928(7) 0.2574(3) 0.0170(5) Uani 1 1 d . . . . .
O2 O 0.4426(4) 0.55485(7) 0.3165(3) 0.0155(4) Uani 1 1 d . . . . .
O3 O 1.1730(4) 0.34194(8) 0.3283(4) 0.0273(6) Uani 1 1 d . . . . .
O4 O 1.2500(4) 0.39934(8) 0.4923(3) 0.0222(5) Uani 1 1 d . . . . .
O5 O -0.0591(4) 0.66001(7) 0.2392(3) 0.0207(5) Uani 1 1 d . . . . .
O6 O -0.1241(4) 0.60158(8) 0.0796(3) 0.0207(5) Uani 1 1 d . . . . .
N1 N 0.8267(5) 0.50197(9) 0.4314(4) 0.0173(5) Uani 1 1 d . . . . .
N2 N 0.9726(4) 0.46688(9) 0.4507(4) 0.0169(5) Uani 1 1 d . . . . .
N3 N 0.3097(5) 0.50181(9) 0.1397(4) 0.0166(5) Uani 1 1 d . . . . .
N4 N 0.1599(4) 0.53663(9) 0.1216(4) 0.0169(5) Uani 1 1 d . . . . .
N5 N 0.9399(5) 0.39561(10) 0.2980(4) 0.0187(6) Uani 1 1 d . . . . .
N6 N 1.1280(5) 0.37935(9) 0.3756(4) 0.0182(5) Uani 1 1 d . . . . .
N7 N 0.1830(4) 0.60760(9) 0.2764(4) 0.0162(5) Uani 1 1 d . . . . .
N8 N -0.0064(4) 0.62289(9) 0.1959(4) 0.0164(5) Uani 1 1 d . . . . .
C1 C 0.6642(5) 0.48999(10) 0.3182(4) 0.0146(6) Uani 1 1 d . . . . .
C2 C 0.8848(5) 0.43649(10) 0.3451(4) 0.0149(6) Uani 1 1 d . . . . .
C3 C 0.4687(5) 0.51424(10) 0.2533(4) 0.0148(6) Uani 1 1 d . . . . .
C4 C 0.2440(5) 0.56691(10) 0.2280(4) 0.0152(6) Uani 1 1 d . . . . .
O1W O 0.453(2) 0.2715(4) 0.3196(16) 0.0492(12) Uiso 0.5 1 d G . P A 1
H1WA H 0.398220 0.254872 0.236123 0.074 Uiso 0.5 1 d G U P A 1
H1WB H 0.564514 0.283350 0.271602 0.074 Uiso 0.5 1 d G U P A 1
O1X O 0.432(2) 0.2734(4) 0.3499(15) 0.0492(12) Uiso 0.5 1 d G . P B 2
H1XA H 0.507052 0.277429 0.451248 0.074 Uiso 0.5 1 d G U P B 2
H1XB H 0.306062 0.285152 0.365357 0.074 Uiso 0.5 1 d G U P B 2
O2W O 0.3752(4) 0.48681(7) 0.6613(4) 0.0216(5) Uani 1 1 d G . . . .
H2WA H 0.494157 0.473026 0.693341 0.032 Uiso 1 1 d G U . . .
H2WB H 0.285633 0.467617 0.617808 0.032 Uiso 1 1 d G U . . .
O3W O 0.7645(4) 0.51408(8) 0.9097(4) 0.0214(5) Uani 1 1 d G . . . .
H3WA H 0.644655 0.528808 0.896217 0.032 Uiso 1 1 d G U . . .
H3WB H 0.850850 0.529305 0.980075 0.032 Uiso 1 1 d G U . . .
O4W O 0.741(4) 0.3267(7) 0.109(3) 0.022(2) Uani 0.5 1 d G . P C 1
H4WA H 0.642985 0.317621 0.180842 0.033 Uiso 0.5 1 d G U P C 1
H4WB H 0.790416 0.349691 0.159263 0.033 Uiso 0.5 1 d G U P C 1
O4X O 0.724(4) 0.3221(7) 0.143(3) 0.022(2) Uani 0.5 1 d G . P D 2
H4XA H 0.764621 0.344339 0.203186 0.033 Uiso 0.5 1 d G U P D 2
H4XB H 0.843112 0.307339 0.135014 0.033 Uiso 0.5 1 d G U P D 2
O5W O 0.386(5) 0.6771(8) 0.477(4) 0.022(2) Uani 0.5 1 d G . P E 1
H5WA H 0.291801 0.697498 0.485724 0.033 Uiso 0.5 1 d G U P E 1
H5WB H 0.309678 0.656408 0.430286 0.033 Uiso 0.5 1 d G U P E 1
O5X O 0.399(5) 0.6821(8) 0.450(4) 0.022(2) Uani 0.5 1 d G . P F 2
H5XA H 0.314105 0.703585 0.424107 0.033 Uiso 0.5 1 d G U P F 2
H5XB H 0.530395 0.691215 0.432517 0.033 Uiso 0.5 1 d G U P F 2
O7 O 0.4963(4) 0.58647(7) 0.8114(3) 0.0164(4) Uani 1 1 d . . . . .
H8 H -0.357(11) 0.596(2) 0.688(8) 0.056(17) Uiso 1 1 d . . . . .
O8 O -0.2349(4) 0.60980(7) 0.5801(3) 0.0155(4) Uani 1 1 d . . . . .
O9 O -0.0093(4) 0.74779(8) 0.8892(4) 0.0210(5) Uani 1 1 d . . . . .
O10 O 0.3035(4) 0.73220(8) 1.0402(4) 0.0229(5) Uani 1 1 d . . . . .
N9 N 0.3148(4) 0.61314(8) 0.7955(4) 0.0139(5) Uani 1 1 d . . . . .
N10 N -0.0499(4) 0.62534(8) 0.6795(4) 0.0137(5) Uani 1 1 d . . . . .
N11 N 0.1144(4) 0.55859(8) 0.6500(4) 0.0142(5) Uani 1 1 d . . . . .
H11A H 0.227718 0.541705 0.668162 0.017 Uiso 1 1 calc R U . . .
H11B H -0.006416 0.549267 0.593872 0.017 Uiso 1 1 calc R U . . .
N12 N -0.2099(4) 0.69190(9) 0.6664(4) 0.0167(5) Uani 1 1 d . . . . .
H12A H -0.316314 0.680745 0.597720 0.020 Uiso 1 1 calc R U . . .
H12B H -0.213373 0.718826 0.693656 0.020 Uiso 1 1 calc R U . . .
N13 N 0.5019(4) 0.65773(9) 0.9967(4) 0.0160(5) Uani 1 1 d . . . . .
H13A H 0.604168 0.638232 1.006289 0.019 Uiso 1 1 calc R U . . .
H13B H 0.517116 0.681239 1.058567 0.019 Uiso 1 1 calc R U . . .
N14 N 0.1461(4) 0.72193(9) 0.9298(4) 0.0167(5) Uani 1 1 d . . . . .
C5 C 0.1259(5) 0.59799(10) 0.7070(4) 0.0134(6) Uani 1 1 d . . . . .
C6 C -0.0450(5) 0.66825(10) 0.7285(4) 0.0140(6) Uani 1 1 d . . . . .
C7 C 0.1410(5) 0.68086(10) 0.8506(4) 0.0150(6) Uani 1 1 d . . . . .
C8 C 0.3232(5) 0.65164(10) 0.8881(4) 0.0145(6) Uani 1 1 d . . . . .
O11 O -0.3548(4) 0.41383(7) 0.7592(3) 0.0169(4) Uani 1 1 d . . . . .
H12 H 0.491(8) 0.4014(15) 0.885(7) 0.029(11) Uiso 1 1 d . . . . .
O12 O 0.3763(4) 0.39184(7) 0.9937(3) 0.0175(5) Uani 1 1 d . . . . .
O13 O 0.1584(5) 0.25304(8) 0.6909(4) 0.0343(7) Uani 1 1 d . . . . .
O14 O -0.1638(5) 0.26637(9) 0.5525(4) 0.0283(6) Uani 1 1 d . . . . .
N15 N -0.1731(5) 0.38728(9) 0.7775(4) 0.0159(5) Uani 1 1 d . . . . .
N16 N 0.1912(4) 0.37596(9) 0.8947(4) 0.0151(5) Uani 1 1 d . . . . .
N17 N 0.0252(4) 0.44282(8) 0.9215(4) 0.0151(5) Uani 1 1 d . . . . .
H17A H 0.145472 0.452348 0.977944 0.018 Uiso 1 1 calc R U . . .
H17B H -0.088261 0.459584 0.902032 0.018 Uiso 1 1 calc R U . . .
N18 N 0.3556(5) 0.30992(9) 0.9073(4) 0.0216(6) Uani 1 1 d . . . . .
H18A H 0.463380 0.321408 0.973326 0.026 Uiso 1 1 calc R U . . .
H18B H 0.359655 0.282951 0.880892 0.026 Uiso 1 1 calc R U . . .
N19 N -0.3618(5) 0.34092(10) 0.5849(4) 0.0210(6) Uani 1 1 d . . . . .
H19A H -0.463900 0.360395 0.571824 0.025 Uiso 1 1 calc R U . . .
H19B H -0.377452 0.316820 0.527491 0.025 Uiso 1 1 calc R U . . .
N20 N -0.0003(5) 0.27767(9) 0.6559(4) 0.0225(6) Uani 1 1 d . . . . .
C9 C 0.0152(5) 0.40348(9) 0.8664(4) 0.0125(6) Uani 1 1 d . . . . .
C10 C 0.1864(5) 0.33332(10) 0.8473(4) 0.0166(6) Uani 1 1 d . . . . .
C11 C 0.0004(6) 0.31945(10) 0.7316(5) 0.0179(6) Uani 1 1 d . . . . .
C12 C -0.1821(6) 0.34799(10) 0.6925(4) 0.0166(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.349(4) . ?
O1 C2 1.371(4) . ?
O2 C3 1.354(4) . ?
O2 C4 1.371(4) . ?
O3 N6 1.245(4) . ?
O4 N6 1.253(4) . ?
O5 N8 1.240(4) . ?
O6 N8 1.258(4) . ?
N1 N2 1.397(4) . ?
N1 C1 1.293(4) . ?
N2 C2 1.309(4) . ?
N3 N4 1.405(4) . ?
N3 C3 1.285(4) . ?
N4 C4 1.301(4) . ?
N5 N6 1.329(4) . ?
N5 C2 1.360(4) . ?
N7 N8 1.333(4) . ?
N7 C4 1.366(4) . ?
C1 C3 1.447(4) . ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8498 . ?
O1X H1XA 0.8504 . ?
O1X H1XB 0.8501 . ?
O2W H2WA 0.8508 . ?
O2W H2WB 0.8504 . ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8504 . ?
O4W H4WA 0.8498 . ?
O4W H4WB 0.8499 . ?
O4X H4XA 0.8496 . ?
O4X H4XB 0.8507 . ?
O5W H5WA 0.8512 . ?
O5W H5WB 0.8495 . ?
O5X H5XA 0.8504 . ?
O5X H5XB 0.8497 . ?
O7 N9 1.363(3) . ?
O8 H8 1.18(6) . ?
O8 N10 1.375(3) . ?
O9 N14 1.250(4) . ?
O10 N14 1.245(4) . ?
N9 C5 1.353(4) . ?
N9 C8 1.372(4) . ?
N10 C5 1.356(4) . ?
N10 C6 1.380(4) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N11 C5 1.293(4) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N12 C6 1.290(4) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
N13 C8 1.307(4) . ?
N14 C7 1.400(4) . ?
C6 C7 1.439(4) . ?
C7 C8 1.431(4) . ?
O11 N15 1.363(3) . ?
O12 H12 1.11(5) . ?
O12 N16 1.378(3) . ?
O13 N20 1.233(4) . ?
O14 N20 1.251(4) . ?
N15 C9 1.363(4) . ?
N15 C12 1.368(4) . ?
N16 C9 1.361(4) . ?
N16 C10 1.369(4) . ?
N17 H17A 0.8600 . ?
N17 H17B 0.8600 . ?
N17 C9 1.287(4) . ?
N18 H18A 0.8600 . ?
N18 H18B 0.8600 . ?
N18 C10 1.301(4) . ?
N19 H19A 0.8600 . ?
N19 H19B 0.8600 . ?
N19 C12 1.312(5) . ?
N20 C11 1.409(4) . ?
C10 C11 1.424(5) . ?
C11 C12 1.421(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 102.6(2) . . ?
C3 O2 C4 101.9(3) . . ?
C1 N1 N2 106.4(3) . . ?
C2 N2 N1 106.0(3) . . ?
C3 N3 N4 105.9(3) . . ?
C4 N4 N3 106.1(3) . . ?
N6 N5 C2 117.2(3) . . ?
O3 N6 O4 121.6(3) . . ?
O3 N6 N5 115.2(3) . . ?
O4 N6 N5 123.2(3) . . ?
N8 N7 C4 116.6(3) . . ?
O5 N8 O6 121.3(3) . . ?
O5 N8 N7 116.1(3) . . ?
O6 N8 N7 122.6(3) . . ?
O1 C1 C3 118.3(2) . . ?
N1 C1 O1 113.2(3) . . ?
N1 C1 C3 128.5(3) . . ?
N2 C2 O1 111.9(3) . . ?
N2 C2 N5 136.6(3) . . ?
N5 C2 O1 111.5(3) . . ?
O2 C3 C1 118.6(2) . . ?
N3 C3 O2 113.9(3) . . ?
N3 C3 C1 127.5(3) . . ?
N4 C4 O2 112.2(3) . . ?
N4 C4 N7 136.2(3) . . ?
N7 C4 O2 111.5(3) . . ?
H1WA O1W H1WB 104.5 . . ?
H1XA O1X H1XB 104.5 . . ?
H2WA O2W H2WB 104.4 . . ?
H3WA O3W H3WB 104.5 . . ?
H4WA O4W H4WB 104.4 . . ?
H4XA O4X H4XB 104.6 . . ?
H5WA O5W H5WB 104.5 . . ?
H5XA O5X H5XB 104.5 . . ?
N10 O8 H8 107(3) . . ?
O7 N9 C8 118.6(2) . . ?
C5 N9 O7 117.8(2) . . ?
C5 N9 C8 123.1(3) . . ?
O8 N10 C6 118.7(3) . . ?
C5 N10 O8 116.8(2) . . ?
C5 N10 C6 124.1(3) . . ?
H11A N11 H11B 120.0 . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C6 N12 H12A 120.0 . . ?
C6 N12 H12B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C8 N13 H13A 120.0 . . ?
C8 N13 H13B 120.0 . . ?
O9 N14 C7 119.2(3) . . ?
O10 N14 O9 120.9(3) . . ?
O10 N14 C7 119.9(3) . . ?
N9 C5 N10 118.1(3) . . ?
N11 C5 N9 120.7(3) . . ?
N11 C5 N10 121.2(3) . . ?
N10 C6 C7 115.3(3) . . ?
N12 C6 N10 117.0(3) . . ?
N12 C6 C7 127.6(3) . . ?
N14 C7 C6 120.1(3) . . ?
N14 C7 C8 120.0(3) . . ?
C8 C7 C6 119.9(3) . . ?
N9 C8 C7 116.8(3) . . ?
N13 C8 N9 115.5(3) . . ?
N13 C8 C7 127.7(3) . . ?
N16 O12 H12 103(2) . . ?
O11 N15 C9 117.0(3) . . ?
O11 N15 C12 118.9(3) . . ?
C9 N15 C12 123.8(3) . . ?
C9 N16 O12 116.4(2) . . ?
C9 N16 C10 124.3(3) . . ?
C10 N16 O12 118.9(3) . . ?
H17A N17 H17B 120.0 . . ?
C9 N17 H17A 120.0 . . ?
C9 N17 H17B 120.0 . . ?
H18A N18 H18B 120.0 . . ?
C10 N18 H18A 120.0 . . ?
C10 N18 H18B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
C12 N19 H19A 120.0 . . ?
C12 N19 H19B 120.0 . . ?
O13 N20 O14 121.1(3) . . ?
O13 N20 C11 120.3(3) . . ?
O14 N20 C11 118.7(3) . . ?
N16 C9 N15 116.7(3) . . ?
N17 C9 N15 121.5(3) . . ?
N17 C9 N16 121.7(3) . . ?
N16 C10 C11 116.6(3) . . ?
N18 C10 N16 116.8(3) . . ?
N18 C10 C11 126.6(3) . . ?
N20 C11 C10 119.7(3) . . ?
N20 C11 C12 120.6(3) . . ?
C12 C11 C10 119.6(3) . . ?
N15 C12 C11 117.0(3) . . ?
N19 C12 N15 115.5(3) . . ?
N19 C12 C11 127.5(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
O1W H1WA O9 0.85 2.46 3.072(13) 129.8 2_546 yes
O1W H1WA N12 0.85 2.38 2.871(13) 117.2 2_546 yes
O1W H1WB O4W 0.85 2.11 2.91(2) 158.3 . yes
O1X H1XA O14 0.85 2.09 2.766(14) 136.2 1_655 yes
O1X H1XA N19 0.85 2.32 2.934(13) 129.7 1_655 yes
O1X H1XB O3 0.85 1.95 2.632(13) 136.8 1_455 yes
O2W H2WA O3W 0.85 2.54 2.990(3) 114.3 . yes
O2W H2WA O11 0.85 2.09 2.850(3) 148.0 1_655 yes
O2W H2WB O4 0.85 2.31 3.059(3) 146.3 1_455 yes
O2W H2WB N2 0.85 2.17 2.848(3) 136.0 1_455 yes
O3W H3WA O7 0.85 2.08 2.830(3) 147.3 . yes
O3W H3WB O6 0.85 2.36 3.045(3) 137.7 1_656 yes
O3W H3WB N4 0.85 2.08 2.837(3) 148.6 1_656 yes
O4W H4WA O1W 0.85 2.11 2.91(2) 156.6 . yes
O4W H4WB O3 0.85 2.55 3.00(3) 114.3 . yes
O4W H4WB N5 0.85 1.94 2.78(3) 170.0 . yes
O4X H4XA O3 0.85 2.56 3.00(3) 113.9 . yes
O4X H4XA N5 0.85 2.01 2.83(3) 162.8 . yes
O4X H4XB O9 0.85 2.11 2.88(2) 151.1 2_646 yes
O5W H5WA O14 0.85 2.28 3.08(3) 155.0 2_556 yes
O5W H5WB N7 0.85 2.01 2.84(3) 166.9 . yes
O5X H5XA O14 0.85 2.16 2.97(3) 159.2 2_556 yes
O5X H5XB N12 0.85 2.24 2.76(3) 119.9 1_655 yes
O8 H8 O7 1.18(6) 1.31(6) 2.489(3) 171(6) 1_455 yes
N11 H11A O2W 0.86 1.92 2.717(3) 153.5 . yes
N11 H11B N1 0.86 2.10 2.878(4) 149.6 1_455 yes
N12 H12A O5W 0.86 1.94 2.75(3) 156.3 1_455 yes
N12 H12A O5X 0.86 1.96 2.76(3) 154.3 1_455 yes
N12 H12B O1W 0.86 2.17 2.871(13) 138.3 2_556 yes
N12 H12B O1X 0.86 2.15 2.858(13) 138.9 2_556 yes
N12 H12B O9 0.86 2.03 2.621(4) 124.8 . yes
N13 H13A O5 0.86 2.65 3.081(4) 112.6 1_656 yes
N13 H13A O6 0.86 2.03 2.871(4) 166.0 1_656 yes
N13 H13B O10 0.86 2.03 2.625(4) 125.3 . yes
O12 H12 O11 1.11(5) 1.38(5) 2.494(3) 176(4) 1_655 yes
N17 H17A N3 0.86 2.14 2.911(4) 148.8 1_556 yes
N17 H17B O3W 0.86 1.91 2.704(4) 153.0 1_455 yes
N18 H18A O4W 0.86 1.89 2.71(3) 159.5 1_556 yes
N18 H18A O4X 0.86 1.93 2.74(3) 156.0 1_556 yes
N18 H18B O13 0.86 2.01 2.606(4) 125.5 . yes
N19 H19A O4 0.86 2.15 2.991(4) 167.1 1_355 yes
N19 H19B O1W 0.86 2.26 3.061(12) 154.0 1_455 yes
N19 H19B O1X 0.86 2.15 2.934(13) 151.5 1_455 yes
N19 H19B O14 0.86 2.02 2.616(4) 125.4 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 O2 178.8(3) . . . . ?
O1 C1 C3 N3 -1.0(4) . . . . ?
N1 N2 C2 O1 -0.5(3) . . . . ?
N1 N2 C2 N5 178.6(4) . . . . ?
N1 C1 C3 O2 -0.8(4) . . . . ?
N1 C1 C3 N3 179.5(4) . . . . ?
N2 N1 C1 O1 -0.1(3) . . . . ?
N2 N1 C1 C3 179.4(3) . . . . ?
N3 N4 C4 O2 0.3(3) . . . . ?
N3 N4 C4 N7 -178.4(3) . . . . ?
N4 N3 C3 O2 0.0(3) . . . . ?
N4 N3 C3 C1 179.8(3) . . . . ?
N6 N5 C2 O1 -179.4(3) . . . . ?
N6 N5 C2 N2 1.5(6) . . . . ?
N8 N7 C4 O2 178.9(2) . . . . ?
N8 N7 C4 N4 -2.3(5) . . . . ?
C1 O1 C2 N2 0.4(3) . . . . ?
C1 O1 C2 N5 -178.9(3) . . . . ?
C1 N1 N2 C2 0.4(3) . . . . ?
C2 O1 C1 N1 -0.2(3) . . . . ?
C2 O1 C1 C3 -179.8(2) . . . . ?
C2 N5 N6 O3 -179.7(3) . . . . ?
C2 N5 N6 O4 2.3(5) . . . . ?
C3 O2 C4 N4 -0.3(3) . . . . ?
C3 O2 C4 N7 178.8(2) . . . . ?
C3 N3 N4 C4 -0.2(3) . . . . ?
C4 O2 C3 N3 0.1(3) . . . . ?
C4 O2 C3 C1 -179.6(2) . . . . ?
C4 N7 N8 O5 -179.2(3) . . . . ?
C4 N7 N8 O6 -0.6(4) . . . . ?
O7 N9 C5 N10 -175.5(3) . . . . ?
O7 N9 C5 N11 4.2(4) . . . . ?
O7 N9 C8 N13 -5.2(4) . . . . ?
O7 N9 C8 C7 172.8(3) . . . . ?
O8 N10 C5 N9 176.4(3) . . . . ?
O8 N10 C5 N11 -3.3(4) . . . . ?
O8 N10 C6 N12 -4.6(4) . . . . ?
O8 N10 C6 C7 172.9(3) . . . . ?
O9 N14 C7 C6 -2.0(5) . . . . ?
O9 N14 C7 C8 176.8(3) . . . . ?
O10 N14 C7 C6 177.6(3) . . . . ?
O10 N14 C7 C8 -3.6(5) . . . . ?
N10 C6 C7 N14 -170.9(3) . . . . ?
N10 C6 C7 C8 10.3(4) . . . . ?
N12 C6 C7 N14 6.2(5) . . . . ?
N12 C6 C7 C8 -172.6(3) . . . . ?
N14 C7 C8 N9 -175.5(3) . . . . ?
N14 C7 C8 N13 2.3(5) . . . . ?
C5 N9 C8 N13 166.6(3) . . . . ?
C5 N9 C8 C7 -15.4(4) . . . . ?
C5 N10 C6 N12 168.6(3) . . . . ?
C5 N10 C6 C7 -13.9(4) . . . . ?
C6 N10 C5 N9 3.1(4) . . . . ?
C6 N10 C5 N11 -176.6(3) . . . . ?
C6 C7 C8 N9 3.3(4) . . . . ?
C6 C7 C8 N13 -178.9(3) . . . . ?
C8 N9 C5 N10 12.6(4) . . . . ?
C8 N9 C5 N11 -167.7(3) . . . . ?
O11 N15 C9 N16 175.9(2) . . . . ?
O11 N15 C9 N17 -3.7(4) . . . . ?
O11 N15 C12 N19 6.0(4) . . . . ?
O11 N15 C12 C11 -173.2(3) . . . . ?
O12 N16 C9 N15 -176.4(3) . . . . ?
O12 N16 C9 N17 3.2(4) . . . . ?
O12 N16 C10 N18 3.0(4) . . . . ?
O12 N16 C10 C11 -174.7(3) . . . . ?
O13 N20 C11 C10 0.6(5) . . . . ?
O13 N20 C11 C12 -179.8(3) . . . . ?
O14 N20 C11 C10 -179.0(3) . . . . ?
O14 N20 C11 C12 0.6(5) . . . . ?
N16 C10 C11 N20 171.0(3) . . . . ?
N16 C10 C11 C12 -8.5(4) . . . . ?
N18 C10 C11 N20 -6.5(5) . . . . ?
N18 C10 C11 C12 173.9(3) . . . . ?
N20 C11 C12 N15 177.3(3) . . . . ?
N20 C11 C12 N19 -1.9(5) . . . . ?
C9 N15 C12 N19 -167.6(3) . . . . ?
C9 N15 C12 C11 13.2(5) . . . . ?
C9 N16 C10 N18 -170.2(3) . . . . ?
C9 N16 C10 C11 12.0(4) . . . . ?
C10 N16 C9 N15 -3.0(4) . . . . ?
C10 N16 C9 N17 176.6(3) . . . . ?
C10 C11 C12 N15 -3.2(5) . . . . ?
C10 C11 C12 N19 177.7(3) . . . . ?
C12 N15 C9 N16 -10.4(4) . . . . ?
C12 N15 C9 N17 170.0(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id JC065
_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 2.215
_oxdiff_exptl_absorpt_empirical_full_min 0.754
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(2)
2 0.4(2)

_vrf_PLAT355_js820e              
;
PROBLEM: Long O-H (X0.82,N0.98A) O12 - H12 . 1.11 Ang.
RESPONSE: These hydrogen positions were located by difference 
map and then refined isotropically.  This is their anticipated distances 
via X-ray diffraction analysis.
;
