# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1993332'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_J8_0m

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H8 N12, H2 O'
_chemical_formula_sum            'C4 H10 N12 O'
_chemical_formula_weight         242.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9678(5)
_cell_length_b                   8.1421(5)
_cell_length_c                   8.4183(6)
_cell_angle_alpha                89.448(2)
_cell_angle_beta                 69.466(2)
_cell_angle_gamma                76.132(2)
_cell_volume                     494.86(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8021
_cell_measurement_theta_min      2.5924
_cell_measurement_theta_max      33.1906

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            12648
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         33.195
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3727
_reflns_number_gt                3189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1014 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
H atoms were freely refined. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3727
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.22910(9) -0.03905(8) 0.73695(8) 0.01961(13) Uani 1 1 d . . . . .
H1A H 0.240(2) -0.0462(19) 0.833(2) 0.038(4) Uiso 1 1 d . . . . .
H2B H 0.143(2) 0.052(2) 0.748(2) 0.045(4) Uiso 1 1 d . . . . .
N1 N 0.16202(9) 0.09736(8) 0.41382(8) 0.01339(12) Uani 1 1 d . . . . .
N2 N -0.01225(9) 0.26362(8) 0.66877(8) 0.01420(12) Uani 1 1 d . . . . .
N3 N -0.16225(9) 0.40185(8) 0.73082(8) 0.01387(12) Uani 1 1 d . . . . .
N4 N -0.10828(8) 0.34716(8) 0.45737(7) 0.01148(11) Uani 1 1 d . . . . .
N5 N -0.36554(10) 0.57587(9) 0.61062(8) 0.01753(13) Uani 1 1 d . . . . .
H5A H -0.3856(18) 0.6085(17) 0.5127(17) 0.026(3) Uiso 1 1 d . . . . .
H5B H -0.427(2) 0.6425(18) 0.7101(19) 0.033(3) Uiso 1 1 d . . . . .
N6 N -0.13067(9) 0.36825(9) 0.29921(8) 0.01498(12) Uani 1 1 d . . . . .
H6A H -0.0238(19) 0.3834(17) 0.2270(18) 0.031(3) Uiso 1 1 d . . . . .
H6B H -0.1409(18) 0.2683(17) 0.2633(17) 0.028(3) Uiso 1 1 d . . . . .
N7 N 0.18145(9) 0.07923(8) 0.25703(7) 0.01288(12) Uani 1 1 d . . . . .
N8 N 0.34054(9) -0.10459(8) 0.01134(8) 0.01424(12) Uani 1 1 d . . . . .
N9 N 0.48445(9) -0.24676(8) -0.04654(8) 0.01441(12) Uani 1 1 d . . . . .
N10 N 0.45013(8) -0.17070(7) 0.21704(7) 0.01116(11) Uani 1 1 d . . . . .
N11 N 0.69810(10) -0.40939(9) 0.07068(8) 0.01763(13) Uani 1 1 d . . . . .
H11A H 0.7118(18) -0.4411(17) 0.1685(18) 0.026(3) Uiso 1 1 d . . . . .
H11B H 0.739(2) -0.4844(19) -0.0164(19) 0.034(4) Uiso 1 1 d . . . . .
N12 N 0.49312(9) -0.17591(8) 0.36635(8) 0.01400(12) Uani 1 1 d . . . . .
H12A H 0.3895(18) -0.1305(16) 0.4560(17) 0.028(3) Uiso 1 1 d . . . . .
H12B H 0.5693(18) -0.1072(17) 0.3553(16) 0.027(3) Uiso 1 1 d . . . . .
C1 C 0.02000(10) 0.23166(9) 0.50614(8) 0.01199(12) Uani 1 1 d . . . . .
C2 C -0.21934(10) 0.44989(9) 0.60128(9) 0.01179(12) Uani 1 1 d . . . . .
C3 C 0.32036(9) -0.05824(9) 0.16798(8) 0.01175(12) Uani 1 1 d . . . . .
C4 C 0.54980(10) -0.28454(9) 0.07930(9) 0.01239(12) 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 H1A 0.840(16) . ?
O1 H2B 0.858(16) . ?
N1 N7 1.2797(8) . ?
N1 C1 1.3734(9) . ?
N2 C1 1.3176(9) . ?
N2 N3 1.3771(9) . ?
N3 C2 1.3430(9) . ?
N4 C2 1.3649(9) . ?
N4 C1 1.3870(9) . ?
N4 N6 1.4076(8) . ?
N5 C2 1.3341(9) . ?
N5 H5A 0.919(13) . ?
N5 H5B 0.911(15) . ?
N6 H6A 0.892(14) . ?
N6 H6B 0.903(13) . ?
N7 C3 1.3712(9) . ?
N8 C3 1.3186(9) . ?
N8 N9 1.3692(9) . ?
N9 C4 1.3387(9) . ?
N10 C4 1.3624(9) . ?
N10 C3 1.3844(9) . ?
N10 N12 1.4118(8) . ?
N11 C4 1.3417(9) . ?
N11 H11A 0.896(14) . ?
N11 H11B 0.873(15) . ?
N12 H12A 0.900(14) . ?
N12 H12B 0.901(13) . ?

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
H1A O1 H2B 104.8(14) . . ?
N7 N1 C1 114.56(6) . . ?
C1 N2 N3 108.19(6) . . ?
C2 N3 N2 107.09(6) . . ?
C2 N4 C1 105.00(6) . . ?
C2 N4 N6 123.30(6) . . ?
C1 N4 N6 131.69(6) . . ?
C2 N5 H5A 119.6(8) . . ?
C2 N5 H5B 118.2(9) . . ?
H5A N5 H5B 120.7(12) . . ?
N4 N6 H6A 106.0(9) . . ?
N4 N6 H6B 107.2(8) . . ?
H6A N6 H6B 106.1(12) . . ?
N1 N7 C3 113.78(6) . . ?
C3 N8 N9 108.54(6) . . ?
C4 N9 N8 106.96(6) . . ?
C4 N10 C3 105.00(6) . . ?
C4 N10 N12 122.38(6) . . ?
C3 N10 N12 132.51(6) . . ?
C4 N11 H11A 117.9(8) . . ?
C4 N11 H11B 115.4(9) . . ?
H11A N11 H11B 119.3(12) . . ?
N10 N12 H12A 109.3(8) . . ?
N10 N12 H12B 106.9(8) . . ?
H12A N12 H12B 106.5(11) . . ?
N2 C1 N1 119.98(6) . . ?
N2 C1 N4 109.79(6) . . ?
N1 C1 N4 130.21(6) . . ?
N5 C2 N3 125.75(7) . . ?
N5 C2 N4 124.30(6) . . ?
N3 C2 N4 109.92(6) . . ?
N8 C3 N7 120.16(6) . . ?
N8 C3 N10 109.40(6) . . ?
N7 C3 N10 130.39(6) . . ?
N9 C4 N11 125.89(6) . . ?
N9 C4 N10 110.09(6) . . ?
N11 C4 N10 123.91(6) . . ?

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
C1 N2 N3 C2 0.65(8) . . . . ?
C1 N1 N7 C3 -178.23(6) . . . . ?
C3 N8 N9 C4 0.08(8) . . . . ?
N3 N2 C1 N1 -179.09(6) . . . . ?
N3 N2 C1 N4 -0.34(8) . . . . ?
N7 N1 C1 N2 -179.46(7) . . . . ?
N7 N1 C1 N4 2.07(11) . . . . ?
C2 N4 C1 N2 -0.10(8) . . . . ?
N6 N4 C1 N2 178.79(7) . . . . ?
C2 N4 C1 N1 178.49(7) . . . . ?
N6 N4 C1 N1 -2.62(13) . . . . ?
N2 N3 C2 N5 177.54(7) . . . . ?
N2 N3 C2 N4 -0.73(8) . . . . ?
C1 N4 C2 N5 -177.78(7) . . . . ?
N6 N4 C2 N5 3.20(11) . . . . ?
C1 N4 C2 N3 0.52(8) . . . . ?
N6 N4 C2 N3 -178.49(6) . . . . ?
N9 N8 C3 N7 -178.31(6) . . . . ?
N9 N8 C3 N10 -0.62(8) . . . . ?
N1 N7 C3 N8 171.44(7) . . . . ?
N1 N7 C3 N10 -5.70(11) . . . . ?
C4 N10 C3 N8 0.90(8) . . . . ?
N12 N10 C3 N8 177.08(7) . . . . ?
C4 N10 C3 N7 178.27(7) . . . . ?
N12 N10 C3 N7 -5.54(13) . . . . ?
N8 N9 C4 N11 -175.87(7) . . . . ?
N8 N9 C4 N10 0.50(8) . . . . ?
C3 N10 C4 N9 -0.85(8) . . . . ?
N12 N10 C4 N9 -177.52(6) . . . . ?
C3 N10 C4 N11 175.60(7) . . . . ?
N12 N10 C4 N11 -1.06(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N8 0.840(16) 1.945(16) 2.7563(9) 162.2(14) 1_556 yes
O1 H2B N2 0.858(16) 2.120(16) 2.9284(9) 156.7(15) . yes
N5 H5A N12 0.919(13) 2.348(13) 3.1678(9) 148.5(11) 1_465 yes
N5 H5B N9 0.911(15) 2.055(15) 2.9456(9) 165.4(13) 1_466 yes
N6 H6A N3 0.892(14) 2.646(13) 3.2690(10) 127.7(11) 2_566 yes
N6 H6B O1 0.903(13) 2.146(13) 3.0139(10) 160.9(12) 2_556 yes
N11 H11A N6 0.896(14) 2.280(14) 3.0709(9) 147.2(11) 1_645 yes
N11 H11B N3 0.873(15) 2.126(15) 2.9694(9) 162.3(13) 1_644 yes
N12 H12A O1 0.900(14) 2.289(14) 3.1208(9) 153.6(11) . yes
N12 H12A N1 0.900(14) 2.383(13) 2.9213(9) 118.5(10) . yes
N12 H12B O1 0.901(13) 2.151(13) 3.0324(10) 165.8(12) 2_656 yes

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_JRY_HNO3_new1_0m
_database_code_depnum_ccdc_archive 'CCDC 1993334'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-07-29 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N12, 2(N O3)'
_chemical_formula_sum            'C4 H10 N14 O6'
_chemical_formula_weight         350.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6892(2)
_cell_length_b                   8.6817(3)
_cell_length_c                   12.0249(5)
_cell_angle_alpha                80.3377(17)
_cell_angle_beta                 75.0338(15)
_cell_angle_gamma                77.9914(14)
_cell_volume                     655.05(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9492
_cell_measurement_theta_min      2.4162
_cell_measurement_theta_max      32.9858

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            29403
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         33.219
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4987
_reflns_number_gt                3554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1117 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
One of the two nitrate anions is disordered by rotation in place. It 
was modeled as disordered over three orientations. The three moieties 
were restrained to have similar geometries as the other not disordered 
nitrate anion. Uij components of ADPs for disordered atoms closer to 
each other than 2.0 Angstrom were restrained to be similar. Subject to 
these conditions the occupancy rates refined to 0.504(3), 0.351(3) 
and 0.145(2). 

H atom positions and thermal parameters were freely refined. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.1558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4987
_refine_ls_number_parameters     332
_refine_ls_number_restraints     325
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.59804(14) 0.98483(10) 0.83067(8) 0.01947(17) Uani 1 1 d . . . . .
N2 N 0.26477(15) 1.07170(11) 0.87189(9) 0.02342(18) Uani 1 1 d . . . . .
H2 H 0.137(3) 1.141(2) 0.8872(16) 0.049(5) Uiso 1 1 d . . . . .
N3 N 0.28763(15) 0.93030(11) 0.82997(9) 0.02495(19) Uani 1 1 d . . . . .
N4 N 0.81326(15) 0.98844(12) 0.81464(10) 0.02542(19) Uani 1 1 d . . . . .
H4A H 0.875(3) 0.985(2) 0.7363(16) 0.041(4) Uiso 1 1 d . . . . .
H4B H 0.872(3) 0.896(2) 0.8548(16) 0.048(5) Uiso 1 1 d . . . . .
N5 N 0.48836(16) 1.23422(12) 0.90298(9) 0.0257(2) Uani 1 1 d . . . . .
H5A H 0.385(3) 1.3103(19) 0.9235(14) 0.034(4) Uiso 1 1 d . . . . .
H5B H 0.617(3) 1.242(2) 0.8955(14) 0.038(4) Uiso 1 1 d . . . . .
N6 N 0.56874(15) 0.73727(11) 0.75816(8) 0.02416(19) Uani 1 1 d . . . . .
N7 N 0.76470(15) 0.69897(11) 0.74708(8) 0.02424(19) Uani 1 1 d . . . . .
N8 N 1.06571(16) 0.50871(13) 0.68398(9) 0.0301(2) Uani 1 1 d . . . . .
N9 N 0.93624(19) 0.35324(13) 0.61341(10) 0.0350(2) Uani 1 1 d . . . . .
H9 H 0.908(3) 0.282(3) 0.5771(18) 0.062(6) Uiso 1 1 d . . . . .
N10 N 0.76927(16) 0.46863(12) 0.65288(9) 0.0294(2) Uani 1 1 d . . . . .
N11 N 1.2183(2) 0.5644(2) 0.71953(15) 0.0524(4) Uani 1 1 d . . . . .
H11A H 1.232(4) 0.660(3) 0.672(2) 0.091(9) Uiso 1 1 d . . . . .
H11B H 1.157(3) 0.587(2) 0.7958(19) 0.062(6) Uiso 1 1 d . . . . .
N12 N 1.3037(3) 0.2895(2) 0.60835(13) 0.0541(4) Uani 1 1 d . . . . .
H12A H 1.328(4) 0.209(3) 0.573(2) 0.090(9) Uiso 1 1 d . . . . .
H12B H 1.396(4) 0.330(3) 0.617(2) 0.069(8) Uiso 1 1 d . . . . .
N13 N -0.12232(14) 1.34831(10) 0.99268(8) 0.02218(18) Uani 1 1 d D . . . .
O1 O -0.09706(13) 1.28265(10) 0.90144(8) 0.02913(19) Uani 1 1 d D . . . .
O2 O 0.02765(13) 1.32517(10) 1.04117(7) 0.02674(17) Uani 1 1 d D . . . .
O3 O -0.29239(13) 1.43011(10) 1.03052(9) 0.0327(2) Uani 1 1 d D . . . .
N14 N 0.770(2) 0.0616(9) 0.4867(8) 0.0296(12) Uani 0.504(3) 1 d D U P A 1
O4 O 0.7978(8) 0.2034(3) 0.4686(4) 0.0603(10) Uani 0.504(3) 1 d D U P A 1
O5 O 0.6534(7) 0.0170(6) 0.5775(4) 0.0655(14) Uani 0.504(3) 1 d D U P A 1
O6 O 0.8592(6) -0.0287(4) 0.4123(3) 0.0509(9) Uani 0.504(3) 1 d D U P A 1
N14B N 0.757(4) 0.0639(17) 0.5010(13) 0.0342(18) Uani 0.351(3) 1 d D U P B 2
O4B O 0.7315(6) 0.1921(7) 0.5411(8) 0.0605(14) Uani 0.351(3) 1 d D U P B 2
O5B O 0.6608(12) -0.0427(7) 0.5578(5) 0.0547(14) Uani 0.351(3) 1 d D U P B 2
O6B O 0.8532(7) 0.0472(8) 0.4036(3) 0.0425(10) Uani 0.351(3) 1 d D U P B 2
N14C N 0.773(6) 0.046(2) 0.4987(19) 0.039(3) Uani 0.145(2) 1 d D U P C 3
O4C O 0.7020(16) 0.1126(16) 0.5898(7) 0.044(2) Uani 0.145(2) 1 d D U P C 3
O5C O 0.7783(16) -0.1008(9) 0.5047(11) 0.059(2) Uani 0.145(2) 1 d D U P C 3
O6C O 0.8894(16) 0.1175(18) 0.4214(11) 0.061(3) Uani 0.145(2) 1 d D U P C 3
C1 C 0.49002(16) 0.87925(12) 0.80550(9) 0.02113(19) Uani 1 1 d . . . . .
C2 C 0.45087(16) 1.10763(12) 0.87059(9) 0.02001(19) Uani 1 1 d . . . . .
C3 C 0.85279(17) 0.56087(13) 0.69555(10) 0.0246(2) Uani 1 1 d . . . . .
C4 C 1.1141(2) 0.37552(16) 0.63257(11) 0.0342(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 C2 1.3517(13) . ?
N1 C1 1.3913(13) . ?
N1 N4 1.4086(13) . ?
N2 C2 1.3406(14) . ?
N2 N3 1.3690(13) . ?
N2 H2 0.929(19) . ?
N3 C1 1.3054(14) . ?
N4 H4A 0.928(18) . ?
N4 H4B 0.929(19) . ?
N5 C2 1.3158(14) . ?
N5 H5A 0.868(17) . ?
N5 H5B 0.855(18) . ?
N6 N7 1.2609(13) . ?
N6 C1 1.3897(14) . ?
N7 C3 1.3913(14) . ?
N8 C4 1.3435(17) . ?
N8 C3 1.3797(15) . ?
N8 N11 1.3996(17) . ?
N9 C4 1.3260(19) . ?
N9 N10 1.3771(14) . ?
N9 H9 0.89(2) . ?
N10 C3 1.2996(16) . ?
N11 H11A 0.93(3) . ?
N11 H11B 0.94(2) . ?
N12 C4 1.3188(18) . ?
N12 H12A 0.84(3) . ?
N12 H12B 0.81(2) . ?
N13 O3 1.2290(12) . ?
N13 O2 1.2512(12) . ?
N13 O1 1.2773(12) . ?
N14 O5 1.221(7) . ?
N14 O6 1.240(7) . ?
N14 O4 1.258(7) . ?
N14B O6B 1.197(10) . ?
N14B O5B 1.245(11) . ?
N14B O4B 1.248(10) . ?
N14C O6C 1.223(14) . ?
N14C O5C 1.255(14) . ?
N14C O4C 1.262(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 106.19(9) . . ?
C2 N1 N4 120.56(9) . . ?
C1 N1 N4 133.07(9) . . ?
C2 N2 N3 111.70(9) . . ?
C2 N2 H2 124.5(12) . . ?
N3 N2 H2 123.0(12) . . ?
C1 N3 N2 104.58(9) . . ?
N1 N4 H4A 107.4(11) . . ?
N1 N4 H4B 107.8(11) . . ?
H4A N4 H4B 107.6(15) . . ?
C2 N5 H5A 119.3(11) . . ?
C2 N5 H5B 117.7(11) . . ?
H5A N5 H5B 122.6(15) . . ?
N7 N6 C1 111.84(9) . . ?
N6 N7 C3 114.13(9) . . ?
C4 N8 C3 106.69(11) . . ?
C4 N8 N11 120.93(11) . . ?
C3 N8 N11 132.29(11) . . ?
C4 N9 N10 112.17(11) . . ?
C4 N9 H9 131.8(14) . . ?
N10 N9 H9 115.9(14) . . ?
C3 N10 N9 103.66(10) . . ?
N8 N11 H11A 104.0(17) . . ?
N8 N11 H11B 105.9(13) . . ?
H11A N11 H11B 108(2) . . ?
C4 N12 H12A 121.3(19) . . ?
C4 N12 H12B 114.8(18) . . ?
H12A N12 H12B 123(3) . . ?
O3 N13 O2 122.32(10) . . ?
O3 N13 O1 119.31(9) . . ?
O2 N13 O1 118.37(9) . . ?
O5 N14 O6 121.7(7) . . ?
O5 N14 O4 118.8(7) . . ?
O6 N14 O4 119.5(6) . . ?
O6B N14B O5B 118.4(10) . . ?
O6B N14B O4B 121.6(10) . . ?
O5B N14B O4B 119.4(9) . . ?
O6C N14C O5C 122.4(18) . . ?
O6C N14C O4C 114.3(16) . . ?
O5C N14C O4C 119.2(16) . . ?
N3 C1 N6 119.56(9) . . ?
N3 C1 N1 111.23(9) . . ?
N6 C1 N1 129.19(9) . . ?
N5 C2 N2 128.23(10) . . ?
N5 C2 N1 125.49(10) . . ?
N2 C2 N1 106.27(9) . . ?
N10 C3 N8 111.51(10) . . ?
N10 C3 N7 131.08(10) . . ?
N8 C3 N7 117.41(10) . . ?
N12 C4 N9 129.46(16) . . ?
N12 C4 N8 124.58(16) . . ?
N9 C4 N8 105.96(10) . . ?

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
C2 N2 N3 C1 1.30(12) . . . . ?
C1 N6 N7 C3 -177.47(9) . . . . ?
C4 N9 N10 C3 0.35(14) . . . . ?
N2 N3 C1 N6 -178.73(9) . . . . ?
N2 N3 C1 N1 -0.05(12) . . . . ?
N7 N6 C1 N3 -175.39(10) . . . . ?
N7 N6 C1 N1 6.19(16) . . . . ?
C2 N1 C1 N3 -1.17(12) . . . . ?
N4 N1 C1 N3 -176.13(11) . . . . ?
C2 N1 C1 N6 177.36(11) . . . . ?
N4 N1 C1 N6 2.4(2) . . . . ?
N3 N2 C2 N5 179.12(11) . . . . ?
N3 N2 C2 N1 -2.03(12) . . . . ?
C1 N1 C2 N5 -179.23(10) . . . . ?
N4 N1 C2 N5 -3.50(16) . . . . ?
C1 N1 C2 N2 1.88(11) . . . . ?
N4 N1 C2 N2 177.61(9) . . . . ?
N9 N10 C3 N8 0.32(13) . . . . ?
N9 N10 C3 N7 179.26(12) . . . . ?
C4 N8 C3 N10 -0.86(14) . . . . ?
N11 N8 C3 N10 -177.47(15) . . . . ?
C4 N8 C3 N7 -179.96(10) . . . . ?
N11 N8 C3 N7 3.4(2) . . . . ?
N6 N7 C3 N10 3.16(18) . . . . ?
N6 N7 C3 N8 -177.95(10) . . . . ?
N10 N9 C4 N12 179.15(14) . . . . ?
N10 N9 C4 N8 -0.87(15) . . . . ?
C3 N8 C4 N12 -179.01(13) . . . . ?
N11 N8 C4 N12 -1.9(2) . . . . ?
C3 N8 C4 N9 1.01(14) . . . . ?
N11 N8 C4 N9 178.09(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N13 0.929(19) 2.490(19) 3.3500(13) 154.1(15) . yes
N2 H2 O1 0.929(19) 1.770(19) 2.6959(12) 173.9(17) . yes
N2 H2 O2 0.929(19) 2.516(19) 3.1441(13) 125.1(14) . yes
N4 H4A O5 0.928(18) 2.651(18) 3.251(5) 123.0(13) 1_565 yes
N4 H4A O6 0.928(18) 2.217(18) 3.046(4) 148.3(14) 2_766 yes
N4 H4A O6B 0.928(18) 2.142(19) 2.987(4) 150.9(15) 2_766 yes
N4 H4A O4C 0.928(18) 2.351(19) 2.958(8) 122.8(14) 1_565 yes
N4 H4A O6C 0.928(18) 2.31(2) 3.172(13) 155.1(15) 2_766 yes
N4 H4B O2 0.929(19) 2.192(19) 3.1168(13) 173.1(16) 2_677 yes
N5 H5A O2 0.868(17) 2.431(17) 3.1088(13) 135.3(13) . yes
N5 H5A O3 0.868(17) 2.330(16) 3.0824(13) 145.2(14) 2_587 yes
N5 H5B N13 0.855(18) 2.712(17) 3.4365(14) 143.5(14) 1_655 yes
N5 H5B O1 0.855(18) 2.039(18) 2.8851(13) 170.1(16) 1_655 yes
N9 H9 O4 0.89(2) 1.93(2) 2.771(3) 157.4(19) . yes
N9 H9 O6 0.89(2) 2.42(2) 2.894(3) 113.8(16) 2_756 yes
N9 H9 O4B 0.89(2) 1.72(2) 2.532(4) 151(2) . yes
N9 H9 O4C 0.89(2) 2.18(3) 2.948(16) 144.5(19) . yes
N9 H9 O5C 0.89(2) 2.43(2) 2.893(10) 112.6(17) 2_756 yes
N9 H9 O6C 0.89(2) 2.58(3) 3.442(19) 163.7(18) . yes
N11 H11A O4 0.93(3) 1.93(3) 2.774(4) 150(2) 2_766 yes
N11 H11A O4B 0.93(3) 2.64(3) 3.454(10) 146(2) 2_766 yes
N11 H11A O6B 0.93(3) 2.55(3) 3.436(6) 159(2) 2_766 yes
N11 H11A O6C 0.93(3) 2.18(3) 3.041(11) 153(2) 2_766 yes
N11 H11B N13 0.94(2) 2.64(2) 3.5344(18) 160.3(17) 2_677 yes
N11 H11B O2 0.94(2) 2.19(2) 3.1194(17) 168.9(18) 2_677 yes
N11 H11B O3 0.94(2) 2.45(2) 3.1794(18) 134.4(17) 2_677 yes
N12 H12A O5 0.84(3) 2.46(3) 2.958(5) 119(2) 1_655 yes
N12 H12A O6 0.84(3) 2.16(3) 2.781(5) 131(2) 2_756 yes
N12 H12A O5B 0.84(3) 2.29(3) 3.101(6) 162(2) 2_756 yes
N12 H12A O5C 0.84(3) 1.78(3) 2.518(10) 144(3) 2_756 yes
N12 H12B O4B 0.81(2) 2.34(2) 2.754(4) 112(2) 1_655 yes

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1993338'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_J85_1_0m

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N12, C H N6 O2, 4(H2 O)'
_chemical_formula_sum            'C5 H18 N18 O6'
_chemical_formula_weight         426.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9012(4)
_cell_length_b                   15.0471(8)
_cell_length_c                   16.8109(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.012(4)
_cell_angle_gamma                90
_cell_volume                     1745.69(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6846
_cell_measurement_theta_min      2.6286
_cell_measurement_theta_max      79.8561

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.237
_shelx_estimated_absorpt_T_min   0.549
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6248
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            13925
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_max         80.319
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3710
_reflns_number_gt                3087
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1030 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The structure is metrically orthorhombic, but crystallizes in 
P2(1)/n as a pseudomerohedric twin. Application of the twin 
transformation matrix 1 0 0, 0 -1 0, 0 0 -1 yielded close to perfect 
twinning, with a BASF value of 0.479(2). 

H atoms attached to sp2 hybridized nitrogen atoms were positioned 
geometrically and constrained to ride on their parent atoms with 
N-H bond distances were constrained to 0.88 Angstroms. All other 
H atoms were located from difference density Fourier maps and refined. 
N-H bond distances were restrained to 0.88 Angstroms. Water O-H 
distances were restrained to 0.84(2) and H...H distances were to 
1.36(2) Angstrom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0582P)²+0.7079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3710
_refine_ls_number_parameters     311
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.9527(5) -0.18897(19) 0.4276(2) 0.0275(6) Uani 1 1 d . . . . .
C2 C 0.8179(5) -0.06627(18) 0.4683(2) 0.0280(6) Uani 1 1 d . . . . .
C3 C 0.6084(5) 0.13831(18) 0.4275(2) 0.0281(6) Uani 1 1 d . . . . .
C4 C 0.4813(5) 0.26577(19) 0.3924(2) 0.0291(7) Uani 1 1 d . . . . .
C5 C 0.7145(5) 0.53738(19) 0.4593(2) 0.0283(6) Uani 1 1 d . . . . .
N1 N 0.8639(4) -0.11423(16) 0.53165(18) 0.0298(6) Uani 1 1 d . . . . .
N2 N 0.9485(4) -0.19093(16) 0.50664(17) 0.0300(6) Uani 1 1 d . . . . .
N3 N 0.8735(4) -0.11198(15) 0.40027(18) 0.0289(6) Uani 1 1 d . . . . .
N4 N 1.0265(5) -0.25082(17) 0.38045(19) 0.0350(6) Uani 1 1 d D . . . .
H4A H 1.019(6) -0.247(3) 0.3279(12) 0.042 Uiso 1 1 d D U . . .
H4B H 1.073(6) -0.3007(19) 0.401(2) 0.042 Uiso 1 1 d D U . . .
N5 N 0.8589(5) -0.09363(18) 0.31803(18) 0.0354(6) Uani 1 1 d D . . . .
H5A H 0.736(3) -0.089(3) 0.307(3) 0.043 Uiso 1 1 d D U . . .
H5B H 0.908(6) -0.0407(16) 0.311(3) 0.043 Uiso 1 1 d D U . . .
N6 N 0.7309(4) 0.01440(16) 0.47815(17) 0.0286(6) Uani 1 1 d . . . . .
N7 N 0.6945(4) 0.05600(16) 0.41334(17) 0.0299(6) Uani 1 1 d . . . . .
N8 N 0.5697(4) 0.17768(16) 0.49449(17) 0.0307(6) Uani 1 1 d . . . . .
N9 N 0.4902(4) 0.25795(15) 0.47091(17) 0.0287(6) Uani 1 1 d . . . . .
H9 H 0.450071 0.299119 0.504244 0.034 Uiso 1 1 calc R U . . .
N10 N 0.5549(4) 0.18910(16) 0.36335(17) 0.0300(6) Uani 1 1 d . . . . .
N11 N 0.4148(5) 0.33252(17) 0.34998(19) 0.0373(7) Uani 1 1 d D . . . .
H11A H 0.373(6) 0.3823(19) 0.372(2) 0.045 Uiso 1 1 d D U . . .
H11B H 0.437(6) 0.341(3) 0.2986(13) 0.045 Uiso 1 1 d D U . . .
N12 N 0.5770(5) 0.17342(18) 0.28242(18) 0.0382(7) Uani 1 1 d D . . . .
H12A H 0.532(6) 0.1190(16) 0.279(3) 0.046 Uiso 1 1 d D U . . .
H12B H 0.700(3) 0.166(3) 0.269(3) 0.046 Uiso 1 1 d D U . . .
N13 N 0.7676(4) 0.48234(16) 0.39988(16) 0.0292(6) Uani 1 1 d . . . . .
H13 H 0.820432 0.429558 0.406002 0.035 Uiso 1 1 calc R U . . .
N14 N 0.7267(4) 0.52121(17) 0.32962(17) 0.0325(6) Uani 1 1 d . . . . .
N15 N 0.6504(4) 0.59766(16) 0.34644(18) 0.0327(6) Uani 1 1 d . . . . .
N16 N 0.6404(4) 0.61025(15) 0.42524(18) 0.0297(6) Uani 1 1 d . . . . .
N17 N 0.7188(4) 0.53263(16) 0.54009(17) 0.0306(6) Uani 1 1 d . . . . .
N18 N 0.7914(4) 0.45948(17) 0.57211(17) 0.0294(6) Uani 1 1 d . . . . .
O1 O 0.8506(4) 0.39679(14) 0.52894(16) 0.0393(6) Uani 1 1 d . . . . .
O2 O 0.7985(4) 0.45528(16) 0.64557(14) 0.0383(6) Uani 1 1 d . . . . .
O3 O 0.9013(4) 0.31260(15) 0.37703(16) 0.0376(6) Uani 1 1 d D . . . .
H3O1 H 0.929(7) 0.302(3) 0.3302(12) 0.056 Uiso 1 1 d D U . . .
H3O2 H 0.965(6) 0.283(3) 0.4089(19) 0.056 Uiso 1 1 d D U . . .
O4 O 1.0664(5) 0.23157(19) 0.24189(17) 0.0501(7) Uani 1 1 d D . . . .
H4O1 H 1.081(8) 0.2828(19) 0.219(3) 0.075 Uiso 1 1 d D U . . .
H4O2 H 0.998(7) 0.200(3) 0.209(3) 0.075 Uiso 1 1 d D U . . .
O5 O 1.1922(5) 0.04596(18) 0.31332(17) 0.0503(7) Uani 1 1 d D . . . .
H5O1 H 1.182(9) 0.076(3) 0.3552(17) 0.075 Uiso 1 1 d D U . . .
H5O2 H 1.169(9) 0.079(3) 0.2740(19) 0.075 Uiso 1 1 d D U . . .
O6 O 1.0844(4) 0.39191(17) 0.16196(19) 0.0477(7) Uani 1 1 d D . . . .
H6O1 H 1.107(8) 0.378(3) 0.1159(16) 0.072 Uiso 1 1 d D U . . .
H6O2 H 1.147(7) 0.437(2) 0.178(3) 0.072 Uiso 1 1 d D 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
C1 N4 1.324(4) . ?
C1 N2 1.329(4) . ?
C1 N3 1.361(4) . ?
C2 N1 1.325(4) . ?
C2 N6 1.364(4) . ?
C2 N3 1.389(4) . ?
C3 N8 1.301(4) . ?
C3 N10 1.372(4) . ?
C3 N7 1.394(4) . ?
C4 N11 1.314(4) . ?
C4 N9 1.327(5) . ?
C4 N10 1.352(4) . ?
C5 N16 1.338(4) . ?
C5 N13 1.348(4) . ?
C5 N17 1.361(4) . ?
N1 N2 1.360(4) . ?
N3 N5 1.413(4) . ?
N4 H4A 0.887(19) . ?
N4 H4B 0.885(19) . ?
N5 H5A 0.873(19) . ?
N5 H5B 0.875(19) . ?
N6 N7 1.281(4) . ?
N8 N9 1.385(4) . ?
N9 H9 0.8800 . ?
N10 N12 1.389(4) . ?
N11 H11A 0.885(19) . ?
N11 H11B 0.886(19) . ?
N12 H12A 0.878(19) . ?
N12 H12B 0.887(19) . ?
N13 N14 1.348(4) . ?
N13 H13 0.8800 . ?
N14 N15 1.296(4) . ?
N15 N16 1.340(4) . ?
N17 N18 1.324(4) . ?
N18 O2 1.237(4) . ?
N18 O1 1.258(4) . ?
O3 H3O1 0.826(19) . ?
O3 H3O2 0.824(18) . ?
O4 H4O1 0.867(19) . ?
O4 H4O2 0.862(19) . ?
O5 H5O1 0.838(19) . ?
O5 H5O2 0.844(19) . ?
O6 H6O1 0.815(19) . ?
O6 H6O2 0.843(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N2 126.2(3) . . ?
N4 C1 N3 123.4(3) . . ?
N2 C1 N3 110.4(3) . . ?
N1 C2 N6 119.5(3) . . ?
N1 C2 N3 109.0(2) . . ?
N6 C2 N3 131.5(3) . . ?
N8 C3 N10 111.8(3) . . ?
N8 C3 N7 129.8(3) . . ?
N10 C3 N7 118.4(3) . . ?
N11 C4 N9 128.6(3) . . ?
N11 C4 N10 126.0(3) . . ?
N9 C4 N10 105.4(3) . . ?
N16 C5 N13 106.9(3) . . ?
N16 C5 N17 118.6(3) . . ?
N13 C5 N17 134.5(3) . . ?
C2 N1 N2 108.4(3) . . ?
C1 N2 N1 107.4(3) . . ?
C1 N3 C2 104.7(3) . . ?
C1 N3 N5 121.7(3) . . ?
C2 N3 N5 133.6(2) . . ?
C1 N4 H4A 122(3) . . ?
C1 N4 H4B 120(3) . . ?
H4A N4 H4B 118(4) . . ?
N3 N5 H5A 107(3) . . ?
N3 N5 H5B 107(3) . . ?
H5A N5 H5B 106(4) . . ?
N7 N6 C2 114.7(3) . . ?
N6 N7 C3 111.9(3) . . ?
C3 N8 N9 103.3(3) . . ?
C4 N9 N8 112.4(3) . . ?
C4 N9 H9 123.8 . . ?
N8 N9 H9 123.8 . . ?
C4 N10 C3 107.0(3) . . ?
C4 N10 N12 122.7(3) . . ?
C3 N10 N12 130.2(3) . . ?
C4 N11 H11A 122(3) . . ?
C4 N11 H11B 125(3) . . ?
H11A N11 H11B 111(4) . . ?
N10 N12 H12A 101(3) . . ?
N10 N12 H12B 112(3) . . ?
H12A N12 H12B 101(4) . . ?
C5 N13 N14 109.0(2) . . ?
C5 N13 H13 125.5 . . ?
N14 N13 H13 125.5 . . ?
N15 N14 N13 106.2(3) . . ?
N14 N15 N16 111.2(3) . . ?
C5 N16 N15 106.7(3) . . ?
N18 N17 C5 117.2(3) . . ?
O2 N18 O1 121.6(3) . . ?
O2 N18 N17 117.6(3) . . ?
O1 N18 N17 120.8(3) . . ?
H3O1 O3 H3O2 113(3) . . ?
H4O1 O4 H4O2 106(3) . . ?
H5O1 O5 H5O2 109(3) . . ?
H6O1 O6 H6O2 114(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 C2 N1 N2 -179.8(3) . . . . ?
N3 C2 N1 N2 -0.1(3) . . . . ?
N4 C1 N2 N1 178.9(3) . . . . ?
N3 C1 N2 N1 0.4(3) . . . . ?
C2 N1 N2 C1 -0.2(3) . . . . ?
N4 C1 N3 C2 -179.0(3) . . . . ?
N2 C1 N3 C2 -0.5(3) . . . . ?
N4 C1 N3 N5 2.0(5) . . . . ?
N2 C1 N3 N5 -179.5(3) . . . . ?
N1 C2 N3 C1 0.4(3) . . . . ?
N6 C2 N3 C1 -180.0(3) . . . . ?
N1 C2 N3 N5 179.2(3) . . . . ?
N6 C2 N3 N5 -1.2(6) . . . . ?
N1 C2 N6 N7 179.2(3) . . . . ?
N3 C2 N6 N7 -0.4(5) . . . . ?
C2 N6 N7 C3 -179.1(3) . . . . ?
N8 C3 N7 N6 3.1(5) . . . . ?
N10 C3 N7 N6 -177.8(3) . . . . ?
N10 C3 N8 N9 -0.8(3) . . . . ?
N7 C3 N8 N9 178.4(3) . . . . ?
N11 C4 N9 N8 -180.0(3) . . . . ?
N10 C4 N9 N8 0.4(3) . . . . ?
C3 N8 N9 C4 0.2(3) . . . . ?
N11 C4 N10 C3 179.5(3) . . . . ?
N9 C4 N10 C3 -0.9(3) . . . . ?
N11 C4 N10 N12 3.0(5) . . . . ?
N9 C4 N10 N12 -177.4(3) . . . . ?
N8 C3 N10 C4 1.1(4) . . . . ?
N7 C3 N10 C4 -178.2(3) . . . . ?
N8 C3 N10 N12 177.3(3) . . . . ?
N7 C3 N10 N12 -2.0(5) . . . . ?
N16 C5 N13 N14 0.1(3) . . . . ?
N17 C5 N13 N14 178.9(4) . . . . ?
C5 N13 N14 N15 -0.1(3) . . . . ?
N13 N14 N15 N16 0.1(4) . . . . ?
N13 C5 N16 N15 0.0(3) . . . . ?
N17 C5 N16 N15 -179.1(3) . . . . ?
N14 N15 N16 C5 0.0(4) . . . . ?
N16 C5 N17 N18 179.4(3) . . . . ?
N13 C5 N17 N18 0.7(6) . . . . ?
C5 N17 N18 O2 178.9(3) . . . . ?
C5 N17 N18 O1 -1.1(5) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1993340'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_J_1_16_salt_0m

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N12, 2(C N5 O2)'
_chemical_formula_sum            'C6 H10 N22 O4'
_chemical_formula_weight         454.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   5.5317(3)
_cell_length_b                   14.9646(8)
_cell_length_c                   10.6648(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.0683(18)
_cell_angle_gamma                90
_cell_volume                     856.35(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.3935
_cell_measurement_theta_max      33.0426

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7176
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            28936
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         33.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3287
_reflns_number_gt                2692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1030 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.3171P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3287
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.06593(16) 0.55411(6) 0.64889(8) 0.01260(16) Uani 1 1 d . . . . .
C2 C 0.33246(16) 0.63751(6) 0.78605(8) 0.01229(15) Uani 1 1 d . . . . .
C3 C 0.82082(16) 0.36047(6) 0.80497(8) 0.01359(16) Uani 1 1 d . . . . .
N1 N -0.05941(14) 0.50399(5) 0.54383(7) 0.01382(15) Uani 1 1 d . . . . .
N2 N -0.01361(15) 0.55373(5) 0.75485(7) 0.01446(15) Uani 1 1 d . . . . .
N3 N 0.15496(15) 0.60497(5) 0.83974(7) 0.01372(15) Uani 1 1 d . . . . .
H3 H 0.129(3) 0.6177(11) 0.9175(16) 0.029(4) Uiso 1 1 d . . . . .
N4 N 0.27612(14) 0.60703(5) 0.66260(7) 0.01256(14) Uani 1 1 d . . . . .
N5 N 0.52437(15) 0.68845(6) 0.83765(8) 0.01650(16) Uani 1 1 d . . . . .
H5A H 0.622(3) 0.7075(11) 0.7891(16) 0.032(4) Uiso 1 1 d . . . . .
H5B H 0.562(3) 0.6995(11) 0.9201(17) 0.033(4) Uiso 1 1 d . . . . .
N6 N 0.41632(16) 0.63328(6) 0.57548(8) 0.01838(17) Uani 1 1 d . . . . .
H6A H 0.306(3) 0.6474(11) 0.4984(16) 0.030(4) Uiso 1 1 d . . . . .
H6B H 0.505(3) 0.5838(13) 0.5581(17) 0.039(4) Uiso 1 1 d . . . . .
N7 N 0.59605(15) 0.41297(6) 0.77931(8) 0.01679(16) Uani 1 1 d . . . . .
N8 N 0.94766(16) 0.34261(6) 0.92444(8) 0.01788(16) Uani 1 1 d . . . . .
N9 N 1.13906(17) 0.29286(7) 0.90722(8) 0.02090(18) Uani 1 1 d . . . . .
N10 N 1.12102(16) 0.28342(6) 0.78161(8) 0.01731(16) Uani 1 1 d . . . . .
N11 N 0.91791(15) 0.32608(6) 0.71350(8) 0.01536(15) Uani 1 1 d . . . . .
O1 O 0.53418(16) 0.44548(6) 0.87216(8) 0.02793(19) Uani 1 1 d . . . . .
O2 O 0.48053(15) 0.42177(6) 0.66624(7) 0.02340(17) 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
C1 N2 1.3086(11) . ?
C1 N4 1.3849(11) . ?
C1 N1 1.3860(11) . ?
C2 N5 1.3141(12) . ?
C2 N3 1.3425(12) . ?
C2 N4 1.3561(11) . ?
C3 N8 1.3238(12) . ?
C3 N11 1.3266(11) . ?
C3 N7 1.4397(12) . ?
N1 N1 1.2723(15) 3_566 ?
N2 N3 1.3663(11) . ?
N3 H3 0.897(16) . ?
N4 N6 1.4033(11) . ?
N5 H5A 0.880(18) . ?
N5 H5B 0.869(17) . ?
N6 H6A 0.920(17) . ?
N6 H6B 0.933(19) . ?
N7 O1 1.2243(11) . ?
N7 O2 1.2268(11) . ?
N8 N9 1.3429(12) . ?
N9 N10 1.3265(12) . ?
N10 N11 1.3419(11) . ?

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 C1 N4 111.18(7) . . ?
N2 C1 N1 119.25(8) . . ?
N4 C1 N1 129.56(8) . . ?
N5 C2 N3 129.19(8) . . ?
N5 C2 N4 124.98(8) . . ?
N3 C2 N4 105.83(8) . . ?
N8 C3 N11 114.51(8) . . ?
N8 C3 N7 121.62(8) . . ?
N11 C3 N7 123.87(8) . . ?
N1 N1 C1 113.49(9) 3_566 . ?
C1 N2 N3 104.55(7) . . ?
C2 N3 N2 111.90(7) . . ?
C2 N3 H3 128.2(11) . . ?
N2 N3 H3 119.6(11) . . ?
C2 N4 C1 106.48(7) . . ?
C2 N4 N6 121.00(8) . . ?
C1 N4 N6 132.46(7) . . ?
C2 N5 H5A 119.3(11) . . ?
C2 N5 H5B 120.4(11) . . ?
H5A N5 H5B 120.1(16) . . ?
N4 N6 H6A 107.7(10) . . ?
N4 N6 H6B 108.2(11) . . ?
H6A N6 H6B 105.8(15) . . ?
O1 N7 O2 124.83(9) . . ?
O1 N7 C3 117.47(8) . . ?
O2 N7 C3 117.70(8) . . ?
C3 N8 N9 103.37(8) . . ?
N10 N9 N8 109.20(8) . . ?
N9 N10 N11 110.09(8) . . ?
C3 N11 N10 102.82(7) . . ?

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
N2 C1 N1 N1 -167.60(10) . . . 3_566 ?
N4 C1 N1 N1 11.43(16) . . . 3_566 ?
N4 C1 N2 N3 -2.19(10) . . . . ?
N1 C1 N2 N3 177.01(8) . . . . ?
N5 C2 N3 N2 -179.55(9) . . . . ?
N4 C2 N3 N2 0.47(10) . . . . ?
C1 N2 N3 C2 1.07(10) . . . . ?
N5 C2 N4 C1 178.28(9) . . . . ?
N3 C2 N4 C1 -1.74(10) . . . . ?
N5 C2 N4 N6 -4.02(14) . . . . ?
N3 C2 N4 N6 175.96(8) . . . . ?
N2 C1 N4 C2 2.55(10) . . . . ?
N1 C1 N4 C2 -176.54(9) . . . . ?
N2 C1 N4 N6 -174.78(9) . . . . ?
N1 C1 N4 N6 6.13(17) . . . . ?
N8 C3 N7 O1 4.50(14) . . . . ?
N11 C3 N7 O1 -175.63(10) . . . . ?
N8 C3 N7 O2 -175.41(9) . . . . ?
N11 C3 N7 O2 4.46(14) . . . . ?
N11 C3 N8 N9 -0.24(11) . . . . ?
N7 C3 N8 N9 179.65(9) . . . . ?
C3 N8 N9 N10 0.32(11) . . . . ?
N8 N9 N10 N11 -0.30(12) . . . . ?
N8 C3 N11 N10 0.06(11) . . . . ?
N7 C3 N11 N10 -179.82(9) . . . . ?
N9 N10 N11 C3 0.15(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 N8 0.897(16) 1.928(17) 2.8207(11) 173.3(15) 3_667 yes
N5 H5A N10 0.880(18) 2.099(18) 2.9493(12) 162.1(15) 2_756 yes
N5 H5B N9 0.869(17) 2.158(17) 2.9130(12) 145.1(15) 3_767 yes
N6 H6A N11 0.920(17) 2.333(17) 3.2429(12) 170.0(14) 3_666 yes
N6 H6B O2 0.933(19) 2.415(17) 2.8922(11) 111.7(13) 3_666 yes

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1993337'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_JRY_63_MeOH_0m

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N12, Cl O4'
_chemical_formula_sum            'C4 H9 Cl N12 O4'
_chemical_formula_weight         324.68

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   7.4095(6)
_cell_length_b                   8.6931(9)
_cell_length_c                   9.5541(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.797(5)
_cell_angle_gamma                90
_cell_volume                     592.15(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2733
_cell_measurement_theta_min      5.0834
_cell_measurement_theta_max      79.1991

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.343
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3982
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            4375
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.088
_diffrn_reflns_theta_max         80.937
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1237
_reflns_number_gt                1076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1030 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Amine H atoms were refined and restrained to be similar in length. 
The ammonium H atom is located on a two fold axis and is shared between 
two symmetry equivalent N atoms. Both anion and cation are located on 
special positions and each half an ion is within the asymmetric unit. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0886P)²+0.7436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1237
_refine_ls_number_parameters     114
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.500000 0.41534(10) 0.250000 0.0203(3) Uani 1 2 d S T P . .
C1 C 0.3078(4) 0.0530(3) 0.0599(3) 0.0157(5) Uani 1 1 d . . . . .
O1 O 0.6127(4) 0.3197(3) 0.1854(2) 0.0342(6) Uani 1 1 d . . . . .
N1 N 0.2227(3) 0.0066(3) 0.1555(2) 0.0173(5) Uani 1 1 d . . . . .
N2 N 0.0748(3) 0.1047(3) 0.1433(2) 0.0168(5) Uani 1 1 d . . . . .
H2 H 0.000000 0.112(12) 0.250000 0.10(3) Uiso 1 2 d S . P . .
O2 O 0.3827(4) 0.5102(3) 0.1396(3) 0.0369(6) Uani 1 1 d . . . . .
C2 C 0.0734(4) 0.2100(3) 0.0411(3) 0.0161(5) Uani 1 1 d . . . . .
N5 N 0.2525(4) 0.2716(3) -0.1266(2) 0.0199(5) Uani 1 1 d D . . . .
H5A H 0.274(6) 0.208(4) -0.195(4) 0.035(10) Uiso 1 1 d D . . . .
H5B H 0.356(5) 0.326(4) -0.090(4) 0.040(11) Uiso 1 1 d D . . . .
N4 N -0.0478(4) 0.3251(3) 0.0009(3) 0.0220(5) Uani 1 1 d D . . . .
H4A H -0.147(5) 0.327(5) 0.035(5) 0.046(12) Uiso 1 1 d D . . . .
H4B H -0.049(6) 0.380(4) -0.078(3) 0.030(10) Uiso 1 1 d D . . . .
N3 N 0.2178(3) 0.1804(3) -0.0152(2) 0.0158(5) Uani 1 1 d . . . . .
N6 N 0.4619(3) -0.0292(3) 0.0455(2) 0.0178(5) 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
Cl1 O2 1.431(2) 2_655 ?
Cl1 O2 1.431(2) . ?
Cl1 O1 1.432(2) . ?
Cl1 O1 1.432(2) 2_655 ?
C1 N1 1.306(3) . ?
C1 N6 1.385(4) . ?
C1 N3 1.388(3) . ?
N1 N2 1.368(3) . ?
N2 C2 1.336(3) . ?
N2 H2 1.288(6) . ?
C2 N4 1.329(4) . ?
C2 N3 1.347(3) . ?
N5 N3 1.406(3) . ?
N5 H5A 0.90(3) . ?
N5 H5B 0.89(3) . ?
N4 H4A 0.88(3) . ?
N4 H4B 0.89(2) . ?
N6 N6 1.265(4) 3_655 ?

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
O2 Cl1 O2 109.6(2) 2_655 . ?
O2 Cl1 O1 110.09(15) 2_655 . ?
O2 Cl1 O1 108.99(14) . . ?
O2 Cl1 O1 108.99(14) 2_655 2_655 ?
O2 Cl1 O1 110.09(15) . 2_655 ?
O1 Cl1 O1 109.0(2) . 2_655 ?
N1 C1 N6 118.6(2) . . ?
N1 C1 N3 110.6(2) . . ?
N6 C1 N3 130.8(2) . . ?
C1 N1 N2 106.0(2) . . ?
C2 N2 N1 109.6(2) . . ?
C2 N2 H2 129(4) . . ?
N1 N2 H2 118(3) . . ?
N4 C2 N2 126.7(2) . . ?
N4 C2 N3 125.1(2) . . ?
N2 C2 N3 108.2(2) . . ?
N3 N5 H5A 108(3) . . ?
N3 N5 H5B 109(3) . . ?
H5A N5 H5B 108(4) . . ?
C2 N4 H4A 118(3) . . ?
C2 N4 H4B 120(3) . . ?
H4A N4 H4B 119(4) . . ?
C2 N3 C1 105.5(2) . . ?
C2 N3 N5 121.6(2) . . ?
C1 N3 N5 132.9(2) . . ?
N6 N6 C1 113.3(3) 3_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 C1 N1 N2 -178.2(2) . . . . ?
N3 C1 N1 N2 0.0(3) . . . . ?
C1 N1 N2 C2 -0.5(3) . . . . ?
N1 N2 C2 N4 -178.9(3) . . . . ?
N1 N2 C2 N3 0.8(3) . . . . ?
N4 C2 N3 C1 178.9(3) . . . . ?
N2 C2 N3 C1 -0.8(3) . . . . ?
N4 C2 N3 N5 -0.7(4) . . . . ?
N2 C2 N3 N5 179.6(2) . . . . ?
N1 C1 N3 C2 0.5(3) . . . . ?
N6 C1 N3 C2 178.4(3) . . . . ?
N1 C1 N3 N5 -179.9(3) . . . . ?
N6 C1 N3 N5 -2.0(5) . . . . ?
N1 C1 N6 N6 -177.2(3) . . . 3_655 ?
N3 C1 N6 N6 5.0(5) . . . 3_655 ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1993335'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_J72_Mono-Nitrate-hydrate_0m_5

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N12, N O3, H2 O'
_chemical_formula_sum            'C4 H11 N13 O4'
_chemical_formula_weight         305.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.308(3)
_cell_length_b                   16.635(7)
_cell_length_c                   9.625(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.404(14)
_cell_angle_gamma                90
_cell_volume                     1157.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7494
_cell_measurement_theta_min      2.4566
_cell_measurement_theta_max      30.6128

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.290415
_exptl_absorpt_correction_T_max  0.432985
_exptl_absorpt_process_details   
;
TWINABS 2012/1: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            16546
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.1225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2799
_reflns_number_gt                2363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1030 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The crystal under investigation was found to be non-merohedrally 
twinned. The orientation matrices for the two components were 
identified using the program Cell_Now, with the two components 
being related by a 180 degree rotation around the reciprocal 
axis (1 0 -1). The two components were integrated using Saint and 
corrected for absorption using twinabs, resulting in the 
following statistics:

3051 data (1265 unique) involve domain 1 only, mean I/sigma 41.9
3063 data (1243 unique) involve domain 2 only, mean I/sigma 27.5
10648 data (3199 unique) involve 2 domains, mean I/sigma 33.9

The exact twin matrix identified by the integration program was 
found to be: 

 0.31844 -0.00008 -0.68292
-0.00022 -1.00000  0.00027
-1.31582  0.00004 -0.31844

The structure was solved using direct methods with only the 
non-overlapping reflections of component 1. The structure was 
refined using the hklf 5 routine with all reflections of component 
1 (including the overlapping ones), resulting in a BASF value of 
0.297(3).

The Rint value given is for all reflections and is based on 
agreement between observed single and composite intensities 
and those calculated from refined unique intensities and twin 
fractions (TWINABS (Sheldrick, 2012)).

All H atoms were initially located in difference density maps. In 
the final refinement cycles, water H atom positions were refined 
and O-H and H...H distances were restrained to 0.84(2) and 1.36(2) 
Angstrom, respectively. Positions of H atoms of pyramidalized amines 
(N4, N11) were refined N-H and H...H distances were restrained to 
0.88(2) and 1.36(2) Angstrom, respectively. Planar NH2 (N5, N12) 
and NH+ (N1) H atoms were placed in calculated positions. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1563P)²+1.6130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.12(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2799
_refine_ls_number_parameters     210
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0827
_refine_ls_wR_factor_ref         0.2366
_refine_ls_wR_factor_gt          0.2226
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1888(5) 0.7270(2) 0.4473(4) 0.0183(7) Uani 1 1 d . . . . .
C2 C 0.2232(5) 0.5980(2) 0.4870(4) 0.0189(7) Uani 1 1 d . . . . .
C3 C 0.2970(5) 0.92323(19) 0.5499(4) 0.0162(7) Uani 1 1 d . . . . .
C4 C 0.2485(5) 1.0494(2) 0.5022(4) 0.0166(7) Uani 1 1 d . . . . .
N1 N 0.1117(5) 0.61259(18) 0.3662(4) 0.0226(7) Uani 1 1 d . . . . .
H8 H 0.060593 0.574806 0.309322 0.027 Uiso 1 1 calc R U . . .
N2 N 0.0870(5) 0.6927(2) 0.3419(4) 0.0246(7) Uani 1 1 d . . . . .
N3 N 0.2751(4) 0.67045(16) 0.5409(3) 0.0174(6) Uani 1 1 d . . . . .
N4 N 0.3952(5) 0.67810(19) 0.6693(4) 0.0226(7) Uani 1 1 d D . . . .
H4A H 0.333(6) 0.705(2) 0.724(5) 0.027 Uiso 1 1 d D U . . .
H4B H 0.478(5) 0.713(2) 0.651(5) 0.027 Uiso 1 1 d D U . . .
N5 N 0.2722(5) 0.52773(18) 0.5393(4) 0.0225(7) Uani 1 1 d . . . . .
H5A H 0.231080 0.483810 0.494218 0.027 Uiso 1 1 calc R U . . .
H5B H 0.346343 0.524146 0.619801 0.027 Uiso 1 1 calc R U . . .
N6 N 0.1951(5) 0.81015(19) 0.4504(4) 0.0203(6) Uani 1 1 d . . . . .
N7 N 0.3004(4) 0.84101(18) 0.5528(3) 0.0181(6) Uani 1 1 d . . . . .
N8 N 0.3934(4) 0.96602(17) 0.6531(3) 0.0157(6) Uani 1 1 d . . . . .
N9 N 0.3649(5) 1.04591(17) 0.6215(3) 0.0196(7) Uani 1 1 d . . . . .
N10 N 0.2019(4) 0.97525(17) 0.4541(3) 0.0166(6) Uani 1 1 d . . . . .
N11 N 0.0901(5) 0.96149(19) 0.3229(3) 0.0189(7) Uani 1 1 d D . . . .
H11A H 0.014(6) 0.925(2) 0.346(5) 0.023 Uiso 1 1 d D U . . .
H11B H 0.162(6) 0.933(2) 0.276(5) 0.023 Uiso 1 1 d D U . . .
N12 N 0.1809(5) 1.11594(18) 0.4390(4) 0.0225(7) Uani 1 1 d . . . . .
H12A H 0.212873 1.163123 0.476174 0.027 Uiso 1 1 calc DR U . . .
H12B H 0.104083 1.113008 0.359705 0.027 Uiso 1 1 calc DR U . . .
N13 N 0.3905(5) 0.29991(19) 0.6340(4) 0.0235(7) Uani 1 1 d . . . . .
O1 O 0.4278(5) 0.37204(17) 0.6521(3) 0.0310(8) Uani 1 1 d . . . . .
O2 O 0.2985(5) 0.27703(18) 0.5188(4) 0.0358(8) Uani 1 1 d . . . . .
O3 O 0.4399(5) 0.2493(2) 0.7281(4) 0.0403(9) Uani 1 1 d . . . . .
O4 O 0.1280(5) 0.40308(19) 0.3541(4) 0.0317(7) Uani 1 1 d D . . . .
H4OA H 0.036(6) 0.404(3) 0.286(5) 0.048 Uiso 1 1 d D U . . .
H4OB H 0.161(8) 0.3549(16) 0.360(6) 0.048 Uiso 1 1 d D 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
C1 N2 1.298(5) . ?
C1 N6 1.384(4) . ?
C1 N3 1.389(4) . ?
C2 N5 1.302(5) . ?
C2 N1 1.341(5) . ?
C2 N3 1.344(4) . ?
C3 N8 1.337(5) . ?
C3 N7 1.368(4) . ?
C3 N10 1.376(4) . ?
C4 N12 1.323(4) . ?
C4 N9 1.327(4) . ?
C4 N10 1.343(4) . ?
N1 N2 1.361(4) . ?
N1 H8 0.8800 . ?
N3 N4 1.413(4) . ?
N4 H4A 0.869(19) . ?
N4 H4B 0.877(19) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 N7 1.267(4) . ?
N8 N9 1.372(4) . ?
N10 N11 1.419(4) . ?
N11 H11A 0.873(19) . ?
N11 H11B 0.877(19) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N13 O1 1.237(4) . ?
N13 O3 1.251(5) . ?
N13 O2 1.268(5) . ?
O4 H4OA 0.864(19) . ?
O4 H4OB 0.837(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N6 118.0(3) . . ?
N2 C1 N3 111.3(3) . . ?
N6 C1 N3 130.7(3) . . ?
N5 C2 N1 126.5(3) . . ?
N5 C2 N3 127.6(3) . . ?
N1 C2 N3 105.9(3) . . ?
N8 C3 N7 120.7(3) . . ?
N8 C3 N10 108.8(3) . . ?
N7 C3 N10 130.4(3) . . ?
N12 C4 N9 125.7(3) . . ?
N12 C4 N10 123.4(3) . . ?
N9 C4 N10 110.9(3) . . ?
C2 N1 N2 112.0(3) . . ?
C2 N1 H8 124.0 . . ?
N2 N1 H8 124.0 . . ?
C1 N2 N1 104.5(3) . . ?
C2 N3 C1 106.3(3) . . ?
C2 N3 N4 121.5(3) . . ?
C1 N3 N4 132.2(3) . . ?
N3 N4 H4A 105(4) . . ?
N3 N4 H4B 104(4) . . ?
H4A N4 H4B 103(3) . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N7 N6 C1 115.9(3) . . ?
N6 N7 C3 112.4(3) . . ?
C3 N8 N9 107.7(3) . . ?
C4 N9 N8 106.9(3) . . ?
C4 N10 C3 105.6(3) . . ?
C4 N10 N11 122.6(3) . . ?
C3 N10 N11 131.6(3) . . ?
N10 N11 H11A 101(3) . . ?
N10 N11 H11B 104(3) . . ?
H11A N11 H11B 102(4) . . ?
C4 N12 H12A 120.0 . . ?
C4 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
O1 N13 O3 121.1(4) . . ?
O1 N13 O2 119.5(3) . . ?
O3 N13 O2 119.4(4) . . ?
H4OA O4 H4OB 104(3) . . ?

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
N5 C2 N1 N2 179.6(4) . . . . ?
N3 C2 N1 N2 -1.3(5) . . . . ?
N6 C1 N2 N1 178.7(3) . . . . ?
N3 C1 N2 N1 -1.5(5) . . . . ?
C2 N1 N2 C1 1.7(5) . . . . ?
N5 C2 N3 C1 179.4(4) . . . . ?
N1 C2 N3 C1 0.3(4) . . . . ?
N5 C2 N3 N4 -0.5(7) . . . . ?
N1 C2 N3 N4 -179.7(4) . . . . ?
N2 C1 N3 C2 0.8(5) . . . . ?
N6 C1 N3 C2 -179.4(4) . . . . ?
N2 C1 N3 N4 -179.2(4) . . . . ?
N6 C1 N3 N4 0.5(8) . . . . ?
N2 C1 N6 N7 -178.0(4) . . . . ?
N3 C1 N6 N7 2.3(6) . . . . ?
C1 N6 N7 C3 -179.0(3) . . . . ?
N8 C3 N7 N6 177.0(4) . . . . ?
N10 C3 N7 N6 -1.3(6) . . . . ?
N7 C3 N8 N9 179.5(3) . . . . ?
N10 C3 N8 N9 -1.9(4) . . . . ?
N12 C4 N9 N8 177.4(4) . . . . ?
N10 C4 N9 N8 -0.7(4) . . . . ?
C3 N8 N9 C4 1.6(4) . . . . ?
N12 C4 N10 C3 -178.6(4) . . . . ?
N9 C4 N10 C3 -0.4(4) . . . . ?
N12 C4 N10 N11 6.6(6) . . . . ?
N9 C4 N10 N11 -175.2(3) . . . . ?
N8 C3 N10 C4 1.4(4) . . . . ?
N7 C3 N10 C4 179.8(4) . . . . ?
N8 C3 N10 N11 175.5(4) . . . . ?
N7 C3 N10 N11 -6.0(7) . . . . ?

_refine_diff_density_max         0.786
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.123

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1993339'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_J85_MeOH_0m

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H8 N12, 0.5(C4 H10 N12), C H N6 O2, C H4 O'
_chemical_formula_sum            'C8 H18 N24 O3'
_chemical_formula_weight         498.46

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3500(11)
_cell_length_b                   10.7574(17)
_cell_length_c                   12.0071(16)
_cell_angle_alpha                104.533(10)
_cell_angle_beta                 107.050(9)
_cell_angle_gamma                91.660(10)
_cell_volume                     992.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2437
_cell_measurement_theta_min      3.9999
_cell_measurement_theta_max      69.9169

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.168
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            9304
_diffrn_reflns_av_unetI/netI     0.2310
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.001
_diffrn_reflns_theta_max         80.099
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3831
_reflns_number_gt                2108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1030 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
H atoms attached to sp2 hybridized nitrogen atoms were positioned 
geometrically and constrained to ride on their parent atoms with 
N-H bond distances constrained to 0.88 Angstroms. All other 
N-bound H atoms were located from difference density Fourier maps 
and refined. N-H bond distances were restrained to 0.88 Angstroms.
CH3 C-H bond distances were constrained to 0.98 Angstrom, O-H 
distances to 0.84 Angstrom. Methyl CH3 and hydroxyl H atoms were 
allowed to rotate but not to tip to best fit the experimental 
electron density.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3831
_refine_ls_number_parameters     359
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.900
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5981(5) 0.9727(4) 0.7700(3) 0.0250(8) Uani 1 1 d . . . . .
C2 C 0.6790(6) 0.9115(4) 0.4253(4) 0.0376(10) Uani 1 1 d . . . . .
H2C H 0.773033 0.922430 0.394094 0.11(2) Uiso 1 1 calc R . . . .
H2D H 0.670062 0.993411 0.480455 0.10(2) Uiso 1 1 calc R . . . .
H2E H 0.574012 0.885189 0.357765 0.16(3) Uiso 1 1 calc R . . . .
N1 N 0.5628(4) 1.0660(3) 0.8557(2) 0.0243(7) Uani 1 1 d . . . . .
H1 H 0.623181 1.141176 0.894218 0.030(11) Uiso 1 1 calc R . . . .
N2 N 0.4209(4) 1.0251(3) 0.8724(3) 0.0308(7) Uani 1 1 d . . . . .
N3 N 0.3728(4) 0.9087(3) 0.8001(3) 0.0321(8) Uani 1 1 d . . . . .
N4 N 0.4802(4) 0.8724(3) 0.7353(3) 0.0291(7) Uani 1 1 d . . . . .
N5 N 0.7215(4) 0.9683(3) 0.7162(2) 0.0252(7) Uani 1 1 d . . . . .
N6 N 0.8352(4) 1.0694(3) 0.7562(2) 0.0271(7) Uani 1 1 d . . . . .
O1 O 0.8386(4) 1.1624(3) 0.8454(2) 0.0397(7) Uani 1 1 d . . . . .
O2 O 0.9457(3) 1.0708(3) 0.7048(2) 0.0326(7) Uani 1 1 d . . . . .
O3 O 0.7081(3) 0.8145(2) 0.4890(2) 0.0299(6) Uani 1 1 d . . . . .
H3 H 0.703523 0.844936 0.559502 0.079(18) Uiso 1 1 calc R . . . .
C1A C 0.1780(5) 0.4764(3) 0.9077(3) 0.0242(8) Uani 1 1 d . . . . .
C2A C 0.3982(4) 0.6009(3) 0.9228(3) 0.0221(8) Uani 1 1 d . . . . .
C3A C 0.7425(5) 0.6403(3) 0.8239(3) 0.0231(8) Uani 1 1 d . . . . .
C4A C 0.9584(5) 0.7688(3) 0.8367(3) 0.0231(8) Uani 1 1 d . . . . .
N1A N 0.3248(4) 0.6644(3) 0.9994(2) 0.0243(7) Uani 1 1 d . . . . .
N2A N 0.1859(4) 0.5878(3) 0.9918(2) 0.0251(7) Uani 1 1 d . . . . .
N3A N 0.3091(4) 0.4805(3) 0.8629(2) 0.0219(6) Uani 1 1 d . . . . .
N4A N 0.0663(4) 0.3742(3) 0.8741(3) 0.0326(8) Uani 1 1 d D . . . .
H4A H 0.074(5) 0.312(3) 0.813(3) 0.049 Uiso 1 1 d D U . . .
H4B H -0.024(4) 0.373(4) 0.900(4) 0.049 Uiso 1 1 d D U . . .
N5A N 0.3332(4) 0.3727(3) 0.7762(3) 0.0278(7) Uani 1 1 d D . . . .
H5A H 0.324(5) 0.410(3) 0.715(3) 0.042 Uiso 1 1 d D U . . .
H5B H 0.435(3) 0.347(4) 0.799(3) 0.042 Uiso 1 1 d D U . . .
N6A N 0.5404(4) 0.6562(3) 0.9115(2) 0.0247(7) Uani 1 1 d . . . . .
N7A N 0.6006(4) 0.5831(3) 0.8356(2) 0.0247(7) Uani 1 1 d . . . . .
N8A N 0.8053(4) 0.5816(3) 0.7390(2) 0.0273(7) Uani 1 1 d . . . . .
N9A N 0.9394(4) 0.6613(3) 0.7457(2) 0.0236(7) Uani 1 1 d . . . . .
N10A N 0.8350(4) 0.7591(3) 0.8866(2) 0.0213(6) Uani 1 1 d . . . . .
N11A N 1.0750(4) 0.8673(3) 0.8709(3) 0.0296(7) Uani 1 1 d D . . . .
H11A H 1.065(5) 0.927(3) 0.933(3) 0.044 Uiso 1 1 d D U . . .
H11B H 1.159(4) 0.858(4) 0.839(3) 0.044 Uiso 1 1 d D U . . .
N12A N 0.8209(4) 0.8567(3) 0.9857(3) 0.0281(7) Uani 1 1 d D . . . .
H12A H 0.867(5) 0.832(4) 1.052(2) 0.042 Uiso 1 1 d D U . . .
H12B H 0.710(3) 0.858(4) 0.975(4) 0.042 Uiso 1 1 d D U . . .
C1B C 0.1372(4) 0.6954(3) 0.5154(3) 0.0222(8) Uani 1 1 d . . . . .
C2B C 0.3273(4) 0.5611(3) 0.5385(3) 0.0231(8) Uani 1 1 d . . . . .
N1B N 0.2370(4) 0.5462(3) 0.6068(3) 0.0267(7) Uani 1 1 d . . . . .
N2B N 0.1170(4) 0.6300(3) 0.5921(2) 0.0256(7) Uani 1 1 d . . . . .
H2B H 0.038291 0.639365 0.627903 0.031 Uiso 1 1 calc R U . . .
N3B N 0.2706(4) 0.6554(3) 0.4803(2) 0.0208(6) Uani 1 1 d . . . . .
N4B N 0.0424(4) 0.7823(3) 0.4762(3) 0.0298(8) Uani 1 1 d D . . . .
H4C H -0.056(3) 0.789(4) 0.488(4) 0.045 Uiso 1 1 d D U . . .
H4D H 0.078(5) 0.810(4) 0.424(3) 0.045 Uiso 1 1 d D U . . .
N5B N 0.3238(4) 0.7064(3) 0.3986(3) 0.0262(7) Uani 1 1 d D . . . .
H5C H 0.299(5) 0.642(3) 0.331(2) 0.039 Uiso 1 1 d D U . . .
H5D H 0.435(2) 0.722(4) 0.430(3) 0.039 Uiso 1 1 d D U . . .
N6B N 0.4590(4) 0.4873(3) 0.5334(2) 0.0252(7) 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
C1 N4 1.333(5) . ?
C1 N1 1.353(4) . ?
C1 N5 1.364(4) . ?
C2 O3 1.428(4) . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
N1 N2 1.337(4) . ?
N1 H1 0.8800 . ?
N2 N3 1.306(4) . ?
N3 N4 1.355(4) . ?
N5 N6 1.314(4) . ?
N6 O2 1.253(3) . ?
N6 O1 1.262(4) . ?
O3 H3 0.8400 . ?
C1A N4A 1.319(5) . ?
C1A N2A 1.344(4) . ?
C1A N3A 1.358(4) . ?
C2A N1A 1.315(4) . ?
C2A N6A 1.370(5) . ?
C2A N3A 1.383(4) . ?
C3A N8A 1.313(4) . ?
C3A N7A 1.379(5) . ?
C3A N10A 1.384(4) . ?
C4A N11A 1.314(5) . ?
C4A N9A 1.345(4) . ?
C4A N10A 1.349(4) . ?
N1A N2A 1.370(4) . ?
N3A N5A 1.414(4) . ?
N4A H4A 0.874(19) . ?
N4A H4B 0.896(19) . ?
N5A H5A 0.907(19) . ?
N5A H5B 0.888(19) . ?
N6A N7A 1.277(3) . ?
N8A N9A 1.360(4) . ?
N10A N12A 1.413(4) . ?
N11A H11A 0.877(19) . ?
N11A H11B 0.889(19) . ?
N12A H12A 0.888(19) . ?
N12A H12B 0.895(19) . ?
C1B N4B 1.329(4) . ?
C1B N2B 1.334(4) . ?
C1B N3B 1.347(4) . ?
C2B N1B 1.300(4) . ?
C2B N6B 1.381(4) . ?
C2B N3B 1.389(4) . ?
N1B N2B 1.370(4) . ?
N2B H2B 0.8800 . ?
N3B N5B 1.405(3) . ?
N4B H4C 0.875(19) . ?
N4B H4D 0.877(19) . ?
N5B H5C 0.892(19) . ?
N5B H5D 0.891(19) . ?
N6B N6B 1.269(5) 2_666 ?

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
N4 C1 N1 108.0(3) . . ?
N4 C1 N5 119.8(3) . . ?
N1 C1 N5 132.2(4) . . ?
O3 C2 H2C 109.5 . . ?
O3 C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
O3 C2 H2E 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
N2 N1 C1 108.8(3) . . ?
N2 N1 H1 125.6 . . ?
C1 N1 H1 125.6 . . ?
N3 N2 N1 106.4(3) . . ?
N2 N3 N4 111.2(3) . . ?
C1 N4 N3 105.6(3) . . ?
N6 N5 C1 116.6(3) . . ?
O2 N6 O1 119.6(3) . . ?
O2 N6 N5 118.1(3) . . ?
O1 N6 N5 122.3(3) . . ?
C2 O3 H3 109.5 . . ?
N4A C1A N2A 127.1(3) . . ?
N4A C1A N3A 123.1(3) . . ?
N2A C1A N3A 109.8(3) . . ?
N1A C2A N6A 120.6(3) . . ?
N1A C2A N3A 109.4(3) . . ?
N6A C2A N3A 129.9(3) . . ?
N8A C3A N7A 119.8(3) . . ?
N8A C3A N10A 109.7(3) . . ?
N7A C3A N10A 130.4(3) . . ?
N11A C4A N9A 126.5(3) . . ?
N11A C4A N10A 125.5(3) . . ?
N9A C4A N10A 108.0(3) . . ?
C2A N1A N2A 108.6(3) . . ?
C1A N2A N1A 106.8(3) . . ?
C1A N3A C2A 105.3(3) . . ?
C1A N3A N5A 121.0(3) . . ?
C2A N3A N5A 133.7(3) . . ?
C1A N4A H4A 115(3) . . ?
C1A N4A H4B 123(3) . . ?
H4A N4A H4B 120(4) . . ?
N3A N5A H5A 98(2) . . ?
N3A N5A H5B 113(3) . . ?
H5A N5A H5B 110(4) . . ?
N7A N6A C2A 114.2(3) . . ?
N6A N7A C3A 113.7(3) . . ?
C3A N8A N9A 107.1(3) . . ?
C4A N9A N8A 109.0(3) . . ?
C4A N10A C3A 106.1(3) . . ?
C4A N10A N12A 122.0(3) . . ?
C3A N10A N12A 131.9(3) . . ?
C4A N11A H11A 111(3) . . ?
C4A N11A H11B 117(3) . . ?
H11A N11A H11B 130(4) . . ?
N10A N12A H12A 107(3) . . ?
N10A N12A H12B 106(3) . . ?
H12A N12A H12B 109(4) . . ?
N4B C1B N2B 127.4(3) . . ?
N4B C1B N3B 124.8(3) . . ?
N2B C1B N3B 107.8(3) . . ?
N1B C2B N6B 119.4(3) . . ?
N1B C2B N3B 110.6(3) . . ?
N6B C2B N3B 130.0(3) . . ?
C2B N1B N2B 106.0(3) . . ?
C1B N2B N1B 109.9(3) . . ?
C1B N2B H2B 125.1 . . ?
N1B N2B H2B 125.1 . . ?
C1B N3B C2B 105.7(3) . . ?
C1B N3B N5B 121.4(3) . . ?
C2B N3B N5B 132.8(3) . . ?
C1B N4B H4C 119(3) . . ?
C1B N4B H4D 111(3) . . ?
H4C N4B H4D 127(4) . . ?
N3B N5B H5C 105(3) . . ?
N3B N5B H5D 105(3) . . ?
H5C N5B H5D 109(4) . . ?
N6B N6B C2B 113.8(4) 2_666 . ?

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
N4 C1 N1 N2 -1.5(4) . . . . ?
N5 C1 N1 N2 176.2(4) . . . . ?
C1 N1 N2 N3 1.1(4) . . . . ?
N1 N2 N3 N4 -0.4(4) . . . . ?
N1 C1 N4 N3 1.2(4) . . . . ?
N5 C1 N4 N3 -176.8(3) . . . . ?
N2 N3 N4 C1 -0.5(4) . . . . ?
N4 C1 N5 N6 -178.8(3) . . . . ?
N1 C1 N5 N6 3.8(6) . . . . ?
C1 N5 N6 O2 -176.7(3) . . . . ?
C1 N5 N6 O1 4.8(5) . . . . ?
N6A C2A N1A N2A 179.5(3) . . . . ?
N3A C2A N1A N2A 0.0(4) . . . . ?
N4A C1A N2A N1A 178.1(4) . . . . ?
N3A C1A N2A N1A 0.5(4) . . . . ?
C2A N1A N2A C1A -0.3(4) . . . . ?
N4A C1A N3A C2A -178.2(3) . . . . ?
N2A C1A N3A C2A -0.5(4) . . . . ?
N4A C1A N3A N5A -0.2(5) . . . . ?
N2A C1A N3A N5A 177.5(3) . . . . ?
N1A C2A N3A C1A 0.3(4) . . . . ?
N6A C2A N3A C1A -179.1(4) . . . . ?
N1A C2A N3A N5A -177.3(3) . . . . ?
N6A C2A N3A N5A 3.2(6) . . . . ?
N1A C2A N6A N7A 178.8(3) . . . . ?
N3A C2A N6A N7A -1.8(5) . . . . ?
C2A N6A N7A C3A 179.3(3) . . . . ?
N8A C3A N7A N6A -172.0(3) . . . . ?
N10A C3A N7A N6A 5.1(5) . . . . ?
N7A C3A N8A N9A 177.8(3) . . . . ?
N10A C3A N8A N9A 0.2(4) . . . . ?
N11A C4A N9A N8A 179.6(3) . . . . ?
N10A C4A N9A N8A -1.1(4) . . . . ?
C3A N8A N9A C4A 0.6(4) . . . . ?
N11A C4A N10A C3A -179.5(3) . . . . ?
N9A C4A N10A C3A 1.2(4) . . . . ?
N11A C4A N10A N12A -1.2(6) . . . . ?
N9A C4A N10A N12A 179.5(3) . . . . ?
N8A C3A N10A C4A -0.9(4) . . . . ?
N7A C3A N10A C4A -178.2(4) . . . . ?
N8A C3A N10A N12A -178.9(3) . . . . ?
N7A C3A N10A N12A 3.8(6) . . . . ?
N6B C2B N1B N2B -179.3(3) . . . . ?
N3B C2B N1B N2B 1.0(4) . . . . ?
N4B C1B N2B N1B 178.0(4) . . . . ?
N3B C1B N2B N1B -0.4(4) . . . . ?
C2B N1B N2B C1B -0.4(4) . . . . ?
N4B C1B N3B C2B -177.4(3) . . . . ?
N2B C1B N3B C2B 1.0(4) . . . . ?
N4B C1B N3B N5B 1.5(5) . . . . ?
N2B C1B N3B N5B 179.8(3) . . . . ?
N1B C2B N3B C1B -1.3(4) . . . . ?
N6B C2B N3B C1B 179.1(4) . . . . ?
N1B C2B N3B N5B -180.0(3) . . . . ?
N6B C2B N3B N5B 0.4(6) . . . . ?
N1B C2B N6B N6B -178.2(4) . . . 2_666 ?
N3B C2B N6B N6B 1.4(6) . . . 2_666 ?

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
C2 H2E N1 0.98 2.67 3.460(5) 137.5 2_676 yes
N1 H1 O1 0.88 2.07 2.548(4) 113.0 . yes
N1 H1 N1A 0.88 2.12 2.945(4) 156.8 2_677 yes
O3 H3 N5 0.84 1.97 2.781(4) 161.2 . yes
N4A H4A O2 0.874(19) 2.63(3) 3.328(4) 138(4) 1_445 yes
N4A H4B N2A 0.896(19) 2.12(2) 2.984(4) 162(4) 2_567 yes
N5A H5A N1B 0.907(19) 2.20(2) 3.049(4) 156(3) . yes
N5A H5B N1A 0.888(19) 2.69(3) 3.416(4) 140(3) 2_667 yes
N11A H11A N12A 0.877(19) 2.34(4) 2.990(5) 131(4) 2_777 yes
N11A H11B N2 0.889(19) 2.66(4) 3.301(5) 130(3) 1_655 yes
N11A H11B N3 0.889(19) 2.07(2) 2.911(4) 158(4) 1_655 yes
N12A H12A O1 0.888(19) 2.40(4) 3.017(5) 127(3) 2_777 yes
N12A H12A N4A 0.888(19) 2.60(3) 3.346(5) 142(3) 2_667 yes
N12A H12B N2 0.895(19) 2.50(3) 3.110(4) 126(3) 2_677 yes
N12A H12B N6A 0.895(19) 2.38(4) 2.907(5) 118(3) . yes
N2B H2B N9A 0.88 1.81 2.653(4) 160.2 1_455 yes
N4B H4C O3 0.875(19) 2.00(2) 2.867(4) 170(4) 1_455 yes
N4B H4D O2 0.877(19) 2.21(3) 3.012(4) 151(4) 2_676 yes
N4B H4D N5B 0.877(19) 2.43(4) 2.841(4) 109(3) . yes
N5B H5C N8A 0.892(19) 2.39(3) 3.113(5) 139(3) 2_666 yes
N5B H5D O3 0.891(19) 2.29(2) 3.152(4) 163(4) . yes

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1993336'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_JRY_HNO3_1_0m

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N12, Cl O4, H2 O'
_chemical_formula_sum            'C4 H11 Cl N12 O5'
_chemical_formula_weight         342.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   7.6478(4)
_cell_length_b                   18.7539(10)
_cell_length_c                   9.4649(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.3617(16)
_cell_angle_gamma                90
_cell_volume                     1302.54(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9515
_cell_measurement_theta_min      2.7759
_cell_measurement_theta_max      33.2298

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.347
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            40210
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         33.228
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4960
_reflns_number_gt                4518
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1030 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.5919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4960
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.01711(3) 0.46205(2) 0.22287(2) 0.01704(6) Uani 1 1 d . . . . .
N1 N 0.66677(11) 0.12548(4) 0.37638(8) 0.01449(13) Uani 1 1 d . . . . .
H1A H 0.772(2) 0.1003(9) 0.4054(18) 0.027(4) Uiso 1 1 d . . . . .
H1B H 0.683(2) 0.1563(8) 0.3110(17) 0.024(4) Uiso 1 1 d . . . . .
C1 C 0.50621(11) 0.14977(4) 0.55591(9) 0.01125(13) Uani 1 1 d . . . . .
O2 O 0.13407(16) 0.52205(6) 0.26732(14) 0.0469(3) Uani 1 1 d . . . . .
C2 C 0.73239(11) 0.22280(4) 0.57555(9) 0.01085(13) Uani 1 1 d . . . . .
N2 N 0.64417(9) 0.16443(4) 0.49694(8) 0.01058(12) Uani 1 1 d . . . . .
O3 O 0.11062(15) 0.40570(5) 0.17226(12) 0.0375(2) Uani 1 1 d . . . . .
C3 C 1.11048(11) 0.27176(4) 0.46231(8) 0.01040(13) Uani 1 1 d . . . . .
N3 N 0.39401(11) 0.09348(4) 0.51366(10) 0.01774(14) Uani 1 1 d . . . . .
H3A H 0.390(2) 0.0769(9) 0.4252(19) 0.034(4) Uiso 1 1 d . . . . .
H3B H 0.293(2) 0.0933(9) 0.5400(19) 0.031(4) Uiso 1 1 d . . . . .
C4 C 1.33328(11) 0.34870(4) 0.48389(8) 0.01049(13) Uani 1 1 d . . . . .
O4 O -0.14173(12) 0.48252(5) 0.10798(9) 0.02847(17) Uani 1 1 d . . . . .
N4 N 0.50809(10) 0.19570(4) 0.66429(8) 0.01263(12) Uani 1 1 d . . . . .
N5 N 0.65046(10) 0.24199(4) 0.67468(8) 0.01268(12) Uani 1 1 d . . . . .
O5 O 0.59142(12) 0.47078(4) 0.31556(9) 0.02207(15) Uani 1 1 d . . . . .
H5A H 0.524(3) 0.4667(11) 0.230(2) 0.046(6) Uiso 1 1 d . . . . .
H5B H 0.698(3) 0.4621(11) 0.317(3) 0.057(6) Uiso 1 1 d . . . . .
N6 N 0.88292(10) 0.26019(4) 0.56355(8) 0.01209(12) Uani 1 1 d . . . . .
N7 N 0.96005(10) 0.23332(4) 0.47319(8) 0.01200(12) Uani 1 1 d . . . . .
N8 N 1.19394(10) 0.25209(4) 0.36539(8) 0.01202(12) Uani 1 1 d . . . . .
N9 N 1.33382(10) 0.29963(4) 0.38066(8) 0.01173(12) Uani 1 1 d . . . . .
H9 H 1.394(3) 0.3037(10) 0.310(2) 0.042(5) Uiso 1 1 d . . . . .
N10 N 1.44393(11) 0.40332(4) 0.52462(9) 0.01575(14) Uani 1 1 d . . . . .
H10A H 1.513(2) 0.4180(9) 0.4685(19) 0.031(4) Uiso 1 1 d . . . . .
H10B H 1.424(2) 0.4328(9) 0.5941(19) 0.030(4) Uiso 1 1 d . . . . .
N11 N 1.19547(9) 0.33094(4) 0.54122(7) 0.00979(11) Uani 1 1 d . . . . .
N12 N 1.15350(10) 0.37429(4) 0.64813(8) 0.01319(13) Uani 1 1 d . . . . .
H12A H 1.134(2) 0.3460(8) 0.7164(17) 0.025(4) Uiso 1 1 d . . . . .
H12B H 1.048(2) 0.3961(9) 0.6058(18) 0.027(4) Uiso 1 1 d . . . . .
O1 O -0.03984(13) 0.43605(6) 0.34662(10) 0.0351(2) 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
Cl1 O2 1.4253(10) . ?
Cl1 O3 1.4321(8) . ?
Cl1 O4 1.4357(8) . ?
Cl1 O1 1.4445(8) . ?
N1 N2 1.4060(10) . ?
N1 H1A 0.906(17) . ?
N1 H1B 0.881(16) . ?
C1 N4 1.3365(10) . ?
C1 N3 1.3481(11) . ?
C1 N2 1.3535(10) . ?
C2 N5 1.3167(10) . ?
C2 N6 1.3797(10) . ?
C2 N2 1.3873(10) . ?
C3 N8 1.3096(10) . ?
C3 N7 1.3859(10) . ?
C3 N11 1.3923(10) . ?
N3 H3A 0.884(17) . ?
N3 H3B 0.872(17) . ?
C4 N10 1.3154(10) . ?
C4 N9 1.3431(10) . ?
C4 N11 1.3558(10) . ?
N4 N5 1.3741(10) . ?
O5 H5A 0.83(2) . ?
O5 H5B 0.83(2) . ?
N6 N7 1.2719(10) . ?
N8 N9 1.3687(10) . ?
N9 H9 0.91(2) . ?
N10 H10A 0.895(17) . ?
N10 H10B 0.904(17) . ?
N11 N12 1.4038(9) . ?
N12 H12A 0.880(16) . ?
N12 H12B 0.893(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cl1 O3 110.51(7) . . ?
O2 Cl1 O4 109.82(7) . . ?
O3 Cl1 O4 109.86(6) . . ?
O2 Cl1 O1 109.55(7) . . ?
O3 Cl1 O1 108.38(6) . . ?
O4 Cl1 O1 108.68(5) . . ?
N2 N1 H1A 109.0(10) . . ?
N2 N1 H1B 107.7(10) . . ?
H1A N1 H1B 105.4(14) . . ?
N4 C1 N3 126.92(8) . . ?
N4 C1 N2 110.15(7) . . ?
N3 C1 N2 122.80(8) . . ?
N5 C2 N6 119.70(7) . . ?
N5 C2 N2 109.91(7) . . ?
N6 C2 N2 130.39(7) . . ?
C1 N2 C2 104.89(7) . . ?
C1 N2 N1 121.16(7) . . ?
C2 N2 N1 133.86(7) . . ?
N8 C3 N7 118.94(7) . . ?
N8 C3 N11 110.75(7) . . ?
N7 C3 N11 130.30(7) . . ?
C1 N3 H3A 114.0(11) . . ?
C1 N3 H3B 117.2(11) . . ?
H3A N3 H3B 117.8(16) . . ?
N10 C4 N9 127.82(7) . . ?
N10 C4 N11 125.62(7) . . ?
N9 C4 N11 106.55(7) . . ?
C1 N4 N5 107.41(6) . . ?
C2 N5 N4 107.63(7) . . ?
H5A O5 H5B 109(2) . . ?
N7 N6 C2 114.19(7) . . ?
N6 N7 C3 113.31(7) . . ?
C3 N8 N9 105.25(7) . . ?
C4 N9 N8 111.15(7) . . ?
C4 N9 H9 125.4(12) . . ?
N8 N9 H9 121.1(12) . . ?
C4 N10 H10A 120.5(11) . . ?
C4 N10 H10B 117.7(11) . . ?
H10A N10 H10B 119.5(15) . . ?
C4 N11 C3 106.21(6) . . ?
C4 N11 N12 120.50(7) . . ?
C3 N11 N12 132.94(7) . . ?
N11 N12 H12A 107.5(10) . . ?
N11 N12 H12B 107.7(10) . . ?
H12A N12 H12B 106.7(15) . . ?

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
N4 C1 N2 C2 -0.14(9) . . . . ?
N3 C1 N2 C2 -176.29(8) . . . . ?
N4 C1 N2 N1 -177.19(7) . . . . ?
N3 C1 N2 N1 6.65(12) . . . . ?
N5 C2 N2 C1 -0.47(9) . . . . ?
N6 C2 N2 C1 179.59(8) . . . . ?
N5 C2 N2 N1 176.03(8) . . . . ?
N6 C2 N2 N1 -3.90(15) . . . . ?
N3 C1 N4 N5 176.62(8) . . . . ?
N2 C1 N4 N5 0.66(9) . . . . ?
N6 C2 N5 N4 -179.18(7) . . . . ?
N2 C2 N5 N4 0.88(9) . . . . ?
C1 N4 N5 C2 -0.95(9) . . . . ?
N5 C2 N6 N7 174.26(8) . . . . ?
N2 C2 N6 N7 -5.81(13) . . . . ?
C2 N6 N7 C3 179.78(7) . . . . ?
N8 C3 N7 N6 -175.41(7) . . . . ?
N11 C3 N7 N6 5.15(12) . . . . ?
N7 C3 N8 N9 179.83(7) . . . . ?
N11 C3 N8 N9 -0.62(9) . . . . ?
N10 C4 N9 N8 -177.97(8) . . . . ?
N11 C4 N9 N8 2.63(9) . . . . ?
C3 N8 N9 C4 -1.25(9) . . . . ?
N10 C4 N11 C3 177.73(8) . . . . ?
N9 C4 N11 C3 -2.85(9) . . . . ?
N10 C4 N11 N12 3.63(12) . . . . ?
N9 C4 N11 N12 -176.95(7) . . . . ?
N8 C3 N11 C4 2.21(9) . . . . ?
N7 C3 N11 C4 -178.31(8) . . . . ?
N8 C3 N11 N12 175.25(8) . . . . ?
N7 C3 N11 N12 -5.26(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O2 0.906(17) 2.450(16) 3.0165(14) 120.8(13) 2_645 yes
N1 H1A O4 0.906(17) 2.411(16) 3.0403(13) 126.6(13) 4_666 yes
N1 H1B N5 0.881(16) 2.277(16) 3.1151(11) 159.0(14) 4_565 yes
N3 H3B O3 0.872(17) 2.124(17) 2.9637(12) 161.4(16) 4_566 yes
O5 H5A N3 0.83(2) 2.30(2) 3.0768(12) 154.8(19) 4_565 yes
O5 H5B Cl1 0.83(2) 2.82(2) 3.6062(8) 159(2) 1_655 yes
O5 H5B O4 0.83(2) 2.63(2) 3.2144(12) 128.7(19) 1_655 yes
O5 H5B O1 0.83(2) 2.00(2) 2.8277(12) 172(2) 1_655 yes
N9 H9 N4 0.91(2) 1.83(2) 2.7416(10) 175.2(18) 4_665 yes
N10 H10A O5 0.895(17) 1.978(17) 2.8365(11) 160.2(16) 1_655 yes
N10 H10B O5 0.904(17) 2.018(17) 2.8576(11) 153.9(15) 3_766 yes
N12 H12A N8 0.880(16) 2.285(16) 3.0957(10) 153.2(14) 4_566 yes
N12 H12B O2 0.893(16) 2.584(16) 3.2013(15) 126.9(13) 3_666 yes
N12 H12B O1 0.893(16) 2.470(16) 3.0487(11) 122.9(13) 1_655 yes

_refine_diff_density_max         0.539
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1993333'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
# was data_J8_2_0m

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H8 N12, H2 O'
_chemical_formula_sum            'C4 H10 N12 O'
_chemical_formula_weight         242.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   11.0909(7)
_cell_length_b                   12.0277(7)
_cell_length_c                   7.0869(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.011(3)
_cell_angle_gamma                90
_cell_volume                     933.71(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6377
_cell_measurement_theta_min      2.5150
_cell_measurement_theta_max      33.1192

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            24491
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.515
_diffrn_reflns_theta_max         33.239
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3582
_reflns_number_gt                2373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1014 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Hydrogen atoms were freely refined. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0648P)²+0.2487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3582
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.22240(10) 0.77748(10) 0.14086(17) 0.0237(2) Uani 1 1 d . . . . .
H1A H 0.213(2) 0.825(2) 0.041(4) 0.053(7) Uiso 1 1 d . . . . .
H1B H 0.258(2) 0.715(2) 0.105(3) 0.053(7) Uiso 1 1 d . . . . .
N1 N 0.20501(10) 0.26027(9) -0.07420(16) 0.0132(2) Uani 1 1 d . . . . .
N2 N 0.23868(10) 0.06118(9) -0.01645(16) 0.0144(2) Uani 1 1 d . . . . .
N3 N 0.17073(10) -0.03144(9) -0.07698(17) 0.0155(2) Uani 1 1 d . . . . .
N4 N 0.07108(9) 0.11504(9) -0.20587(16) 0.0123(2) Uani 1 1 d . . . . .
N5 N -0.01761(11) -0.06410(10) -0.28256(18) 0.0165(2) Uani 1 1 d . . . . .
H5A H -0.0900(19) -0.0353(19) -0.331(3) 0.039(6) Uiso 1 1 d . . . . .
H5B H -0.0174(18) -0.1351(19) -0.243(3) 0.035(5) Uiso 1 1 d . . . . .
N6 N -0.01184(11) 0.18549(10) -0.31830(18) 0.0165(2) Uani 1 1 d . . . . .
H6A H -0.0828(17) 0.1873(17) -0.269(3) 0.030(5) Uiso 1 1 d . . . . .
H6B H -0.0266(18) 0.1550(18) -0.438(3) 0.040(6) Uiso 1 1 d . . . . .
N7 N 0.30654(10) 0.27899(9) 0.03248(16) 0.0132(2) Uani 1 1 d . . . . .
N8 N 0.26807(10) 0.47903(9) -0.00702(16) 0.0143(2) Uani 1 1 d . . . . .
N9 N 0.33218(10) 0.57159(9) 0.06849(17) 0.0146(2) Uani 1 1 d . . . . .
N10 N 0.43556(9) 0.42281(9) 0.17978(15) 0.0117(2) Uani 1 1 d . . . . .
N11 N 0.51394(11) 0.59966(10) 0.29465(17) 0.0161(2) Uani 1 1 d . . . . .
H11A H 0.5897(17) 0.5703(16) 0.344(3) 0.027(5) Uiso 1 1 d . . . . .
H11B H 0.5099(17) 0.6715(18) 0.271(3) 0.030(5) Uiso 1 1 d . . . . .
N12 N 0.52299(10) 0.35049(10) 0.27581(17) 0.0156(2) Uani 1 1 d . . . . .
H12A H 0.5322(16) 0.3686(16) 0.402(3) 0.027(5) Uiso 1 1 d . . . . .
H12B H 0.5969(16) 0.3610(16) 0.234(3) 0.024(5) Uiso 1 1 d . . . . .
C1 C 0.17827(11) 0.14825(11) -0.09483(18) 0.0122(2) Uani 1 1 d . . . . .
C2 C 0.06987(11) 0.00276(11) -0.19070(18) 0.0128(2) Uani 1 1 d . . . . .
C3 C 0.33073(11) 0.39107(10) 0.06040(18) 0.0119(2) Uani 1 1 d . . . . .
C4 C 0.43187(11) 0.53567(11) 0.18311(18) 0.0121(2) 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 H1A 0.90(3) . ?
O1 H1B 0.90(3) . ?
N1 N7 1.2742(15) . ?
N1 C1 1.3825(17) . ?
N2 C1 1.3182(17) . ?
N2 N3 1.3754(15) . ?
N3 C2 1.3370(16) . ?
N4 C2 1.3550(17) . ?
N4 C1 1.3780(16) . ?
N4 N6 1.4032(15) . ?
N5 C2 1.3469(17) . ?
N5 H5A 0.89(2) . ?
N5 H5B 0.90(2) . ?
N6 H6A 0.91(2) . ?
N6 H6B 0.92(2) . ?
N7 C3 1.3827(16) . ?
N8 C3 1.3140(17) . ?
N8 N9 1.3829(15) . ?
N9 C4 1.3370(16) . ?
N10 C4 1.3584(17) . ?
N10 C3 1.3803(16) . ?
N10 N12 1.3976(15) . ?
N11 C4 1.3492(17) . ?
N11 H11A 0.927(19) . ?
N11 H11B 0.88(2) . ?
N12 H12A 0.913(19) . ?
N12 H12B 0.923(18) . ?

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
H1A O1 H1B 108(2) . . ?
N7 N1 C1 112.95(11) . . ?
C1 N2 N3 107.13(10) . . ?
C2 N3 N2 107.73(11) . . ?
C2 N4 C1 105.19(10) . . ?
C2 N4 N6 129.28(11) . . ?
C1 N4 N6 125.40(11) . . ?
C2 N5 H5A 119.4(14) . . ?
C2 N5 H5B 116.8(13) . . ?
H5A N5 H5B 116.5(19) . . ?
N4 N6 H6A 109.0(12) . . ?
N4 N6 H6B 106.9(13) . . ?
H6A N6 H6B 109.0(17) . . ?
N1 N7 C3 113.01(11) . . ?
C3 N8 N9 107.27(10) . . ?
C4 N9 N8 107.52(10) . . ?
C4 N10 C3 105.20(10) . . ?
C4 N10 N12 129.35(11) . . ?
C3 N10 N12 125.44(11) . . ?
C4 N11 H11A 119.4(12) . . ?
C4 N11 H11B 116.1(13) . . ?
H11A N11 H11B 117.4(17) . . ?
N10 N12 H12A 107.0(12) . . ?
N10 N12 H12B 110.0(11) . . ?
H12A N12 H12B 108.4(16) . . ?
N2 C1 N4 110.27(11) . . ?
N2 C1 N1 130.04(11) . . ?
N4 C1 N1 119.63(11) . . ?
N3 C2 N5 125.38(12) . . ?
N3 C2 N4 109.68(11) . . ?
N5 C2 N4 124.89(12) . . ?
N8 C3 N10 110.30(11) . . ?
N8 C3 N7 130.78(12) . . ?
N10 C3 N7 118.90(11) . . ?
N9 C4 N11 126.12(12) . . ?
N9 C4 N10 109.67(11) . . ?
N11 C4 N10 124.11(12) . . ?

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
C1 N2 N3 C2 -0.29(15) . . . . ?
C1 N1 N7 C3 -177.18(11) . . . . ?
C3 N8 N9 C4 -1.01(14) . . . . ?
N3 N2 C1 N4 0.23(15) . . . . ?
N3 N2 C1 N1 177.39(13) . . . . ?
C2 N4 C1 N2 -0.08(15) . . . . ?
N6 N4 C1 N2 -176.21(12) . . . . ?
C2 N4 C1 N1 -177.58(12) . . . . ?
N6 N4 C1 N1 6.29(19) . . . . ?
N7 N1 C1 N2 2.9(2) . . . . ?
N7 N1 C1 N4 179.80(11) . . . . ?
N2 N3 C2 N5 177.84(13) . . . . ?
N2 N3 C2 N4 0.25(15) . . . . ?
C1 N4 C2 N3 -0.11(14) . . . . ?
N6 N4 C2 N3 175.82(12) . . . . ?
C1 N4 C2 N5 -177.72(13) . . . . ?
N6 N4 C2 N5 -1.8(2) . . . . ?
N9 N8 C3 N10 0.05(15) . . . . ?
N9 N8 C3 N7 178.87(14) . . . . ?
C4 N10 C3 N8 0.90(15) . . . . ?
N12 N10 C3 N8 179.96(11) . . . . ?
C4 N10 C3 N7 -178.08(12) . . . . ?
N12 N10 C3 N7 0.98(19) . . . . ?
N1 N7 C3 N8 -1.4(2) . . . . ?
N1 N7 C3 N10 177.33(11) . . . . ?
N8 N9 C4 N11 -174.95(12) . . . . ?
N8 N9 C4 N10 1.60(14) . . . . ?
C3 N10 C4 N9 -1.53(14) . . . . ?
N12 N10 C4 N9 179.45(12) . . . . ?
C3 N10 C4 N11 175.09(12) . . . . ?
N12 N10 C4 N11 -3.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N3 0.90(3) 1.95(3) 2.7779(16) 153(2) 1_565 yes
O1 H1B N9 0.90(3) 1.94(3) 2.8413(16) 171(2) . yes
N5 H5A N8 0.89(2) 2.13(2) 2.9852(17) 160(2) 2_544 yes
N5 H5B N1 0.90(2) 2.60(2) 3.0252(16) 110.1(15) 2_544 yes
N5 H5B N6 0.90(2) 2.21(2) 3.1010(17) 168.6(18) 2_544 yes
N6 H6A O1 0.91(2) 1.96(2) 2.8554(17) 167.6(18) 3_565 yes
N6 H6B N5 0.92(2) 2.38(2) 3.2448(18) 157.7(17) 3_554 yes
N11 H11A N2 0.927(19) 2.099(19) 2.9769(16) 157.6(16) 2_655 yes
N11 H11B N7 0.88(2) 2.62(2) 3.0584(16) 111.9(15) 2_655 yes
N11 H11B N12 0.88(2) 2.20(2) 3.0749(18) 172.8(18) 2_655 yes
N12 H12A N11 0.913(19) 2.32(2) 3.1913(18) 160.6(16) 3_666 yes
N12 H12B O1 0.923(18) 2.292(18) 2.9278(16) 125.6(15) 2_645 yes
N12 H12B N9 0.923(18) 2.530(18) 3.2619(17) 136.5(14) 3_665 yes

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.077

