# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_G117_MSI_NO3_0m
_database_code_depnum_ccdc_archive 'CCDC 2024994'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2021-01-11 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         'C3 H6 N3 O, N O3'
_chemical_formula_sum            'C3 H6 N4 O4'
_chemical_formula_weight         162.12

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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.7481(6)
_cell_length_b                   5.8420(7)
_cell_length_c                   9.9504(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.390(5)
_cell_angle_gamma                90
_cell_volume                     334.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2359
_cell_measurement_theta_min      7.7099
_cell_measurement_theta_max      78.9749

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.306
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_T_max  0.7542
_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 diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            2988
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         7.710
_diffrn_reflns_theta_max         79.262
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             764
_reflns_number_gt                711
_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          
;
Positions of amine 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)+(0.0538P)²+0.0917P] 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         764
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
O1 O 0.2439(2) 0.250000 0.29026(13) 0.0223(3) Uani 1 2 d S T P . .
O2 O 0.8631(2) 0.250000 0.75147(13) 0.0242(4) Uani 1 2 d S T P . .
O3 O 0.6183(2) 0.250000 0.58335(14) 0.0335(4) Uani 1 2 d S T P . .
O4 O 0.4914(3) 0.250000 0.78635(15) 0.0339(4) Uani 1 2 d S T P . .
N1 N 0.1396(3) 0.250000 0.16287(16) 0.0240(4) Uani 1 2 d S T P . .
N2 N -0.0807(3) 0.250000 0.18624(15) 0.0218(4) Uani 1 2 d S T P . .
N3 N 0.1429(3) 0.250000 0.51217(16) 0.0225(4) Uani 1 2 d S T P . .
H3A H 0.296(5) 0.250000 0.535(2) 0.027 Uiso 1 2 d S U P . .
H3B H 0.033(4) 0.250000 0.571(3) 0.027 Uiso 1 2 d S U P . .
N4 N 0.6555(3) 0.250000 0.70870(16) 0.0207(4) Uani 1 2 d S T P . .
C1 C -0.1347(3) 0.250000 0.31674(18) 0.0220(4) Uani 1 2 d S T P . .
H1 H -0.285332 0.250000 0.353916 0.026 Uiso 1 2 calc R U P . .
C2 C 0.0778(3) 0.250000 0.38510(17) 0.0192(4) Uani 1 2 d S T P . .
C3 C -0.2472(4) 0.250000 0.0713(2) 0.0325(5) Uani 1 2 d S T P . .
H3C H -0.164420 0.217972 -0.011556 0.049 Uiso 0.5 1 calc R U P . .
H3D H -0.322587 0.400144 0.064226 0.049 Uiso 0.5 1 calc R U P . .
H3E H -0.365475 0.131884 0.084774 0.049 Uiso 0.5 1 calc R U P . .


_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 C2 1.359(2) . ?
O1 N1 1.389(2) . ?
O2 N4 1.257(2) . ?
O3 N4 1.260(2) . ?
O4 N4 1.234(2) . ?
N1 N2 1.293(2) . ?
N2 C1 1.342(2) . ?
N2 C3 1.473(2) . ?
N3 C2 1.310(2) . ?
N3 H3A 0.90(3) . ?
N3 H3B 0.87(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9500 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C3 H3C 0.980(11) 4_565 ?
C3 H3D 0.980(16) 4_565 ?
C3 H3E 0.98(3) 4_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 N1 109.79(14) . . ?
N2 N1 O1 103.82(14) . . ?
N1 N2 C1 115.09(16) . . ?
N1 N2 C3 118.75(16) . . ?
C1 N2 C3 126.16(17) . . ?
C2 N3 H3A 120.0(16) . . ?
C2 N3 H3B 117.0(16) . . ?
H3A N3 H3B 123(2) . . ?
O4 N4 O2 121.45(16) . . ?
O4 N4 O3 120.39(16) . . ?
O2 N4 O3 118.16(15) . . ?
N2 C1 C2 104.71(16) . . ?
N2 C1 H1 127.6 . . ?
C2 C1 H1 127.6 . . ?
N3 C2 O1 118.77(17) . . ?
N3 C2 C1 134.65(18) . . ?
O1 C2 C1 106.58(15) . . ?
N2 C3 H3C 109.5 . . ?
N2 C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
N2 C3 H3E 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
N2 C3 H3C 109.5(2) . 4_565 ?
N2 C3 H3D 109.5(3) . 4_565 ?
H3C C3 H3D 109.5 4_565 4_565 ?
N2 C3 H3E 109.5(5) . 4_565 ?
H3C C3 H3E 109.5 4_565 4_565 ?
H3D C3 H3E 109.5 4_565 4_565 ?

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 O1 N1 N2 0.000(0) . . . . ?
O1 N1 N2 C1 0.000(0) . . . . ?
O1 N1 N2 C3 180.000(0) . . . . ?
N1 N2 C1 C2 0.000(0) . . . . ?
C3 N2 C1 C2 180.000(0) . . . . ?
N1 O1 C2 N3 180.000(0) . . . . ?
N1 O1 C2 C1 0.000(0) . . . . ?
N2 C1 C2 N3 180.000(0) . . . . ?
N2 C1 C2 O1 0.000(0) . . . . ?

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 H3A O3 0.90(3) 1.90(3) 2.806(2) 180(2) . yes
N3 H3B O2 0.87(3) 2.06(3) 2.905(2) 162(2) 1_455 yes
N3 H3B O3 0.87(3) 2.39(3) 3.114(2) 141(2) 1_455 yes
C1 H1 O3 0.95 2.36 3.039(2) 127.9 1_455 yes
C3 H3C O2 0.98 2.37 3.260(3) 150.0 1_454 yes

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.293
_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_G117_MSI_NT_0m
_database_code_depnum_ccdc_archive 'CCDC 2024995'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2021-01-11 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         'C N5 O2, C3 H6 N3 O'
_chemical_formula_sum            'C4 H6 N8 O3'
_chemical_formula_weight         214.17

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/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                   24.1038(10)
_cell_length_b                   5.0060(2)
_cell_length_c                   15.4562(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.365(3)
_cell_angle_gamma                90
_cell_volume                     1770.01(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      3.8623
_cell_measurement_theta_max      66.5896

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.202
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_T_max  0.7528
_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 diffractometer with PhotonIII_C14 charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            24473
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.864
_diffrn_reflns_theta_max         66.680
_diffrn_reflns_theta_full        66.680
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3112
_reflns_number_gt                2737
_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          
;
Amine H atom positions were refined and N-H distances were 
restrained to be similar to each other. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.5510P] 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       0.00137(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3112
_refine_ls_number_parameters     290
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_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
O1A O 0.18972(4) 0.90404(18) 0.47750(6) 0.0235(2) Uani 1 1 d . . . . .
O2A O 0.07589(5) 0.2800(2) 0.55620(7) 0.0406(3) Uani 1 1 d . . . . .
O3A O 0.17044(5) 0.2789(2) 0.61305(7) 0.0380(3) Uani 1 1 d . . . . .
N1A N 0.09782(5) 0.9056(2) 0.41950(7) 0.0217(2) Uani 1 1 d . . . . .
N2A N 0.13915(5) 0.7713(2) 0.47702(7) 0.0254(3) Uani 1 1 d . . . . .
N3A N 0.21741(5) 1.2718(2) 0.41215(8) 0.0267(3) Uani 1 1 d D . . . .
H3D H 0.2523(6) 1.267(4) 0.4511(10) 0.036(4) Uiso 1 1 d D . . . .
H3E H 0.2061(7) 1.395(3) 0.3716(10) 0.032(4) Uiso 1 1 d D . . . .
N4A N 0.16678(5) 0.6988(2) 0.72092(7) 0.0248(2) Uani 1 1 d . . . . .
N5A N 0.14563(5) 0.8862(2) 0.76345(7) 0.0262(3) Uani 1 1 d . . . . .
N6A N 0.08781(5) 0.8762(2) 0.73533(7) 0.0274(3) Uani 1 1 d . . . . .
N7A N 0.06953(5) 0.6814(2) 0.67330(7) 0.0269(3) Uani 1 1 d . . . . .
N8A N 0.12221(5) 0.3637(2) 0.60845(7) 0.0269(3) Uani 1 1 d . . . . .
C1A C 0.17573(5) 1.1165(3) 0.42069(8) 0.0204(3) Uani 1 1 d . . . . .
C2A C 0.11573(5) 1.1167(3) 0.38192(8) 0.0213(3) Uani 1 1 d . . . . .
H2A H 0.092399 1.238730 0.338471 0.026 Uiso 1 1 calc R U . . .
C3A C 0.03717(6) 0.8194(3) 0.40363(10) 0.0307(3) Uani 1 1 d . . . . .
H3A H 0.021927 0.739205 0.342880 0.046 Uiso 1 1 calc R U . . .
H3B H 0.013184 0.974081 0.407621 0.046 Uiso 1 1 calc R U . . .
H3C H 0.035949 0.687352 0.449809 0.046 Uiso 1 1 calc R U . . .
C4A C 0.11919(5) 0.5820(3) 0.66772(8) 0.0211(3) Uani 1 1 d . . . . .
O1B O 0.31253(4) 0.38489(18) 0.79026(6) 0.0241(2) Uani 1 1 d . . . . .
O2B O 0.41986(5) 1.7242(2) 0.48258(6) 0.0381(3) Uani 1 1 d . . . . .
O3B O 0.32534(5) 1.6988(2) 0.44037(6) 0.0344(2) Uani 1 1 d . . . . .
N1B N 0.40444(5) 0.4056(2) 0.82399(7) 0.0218(2) Uani 1 1 d . . . . .
N2B N 0.36412(5) 0.2615(2) 0.84034(7) 0.0255(3) Uani 1 1 d . . . . .
N3B N 0.28172(5) 0.7468(2) 0.69660(8) 0.0278(3) Uani 1 1 d D . . . .
H3I H 0.2915(7) 0.873(3) 0.6667(10) 0.032(4) Uiso 1 1 d D . . . .
H3J H 0.2465(6) 0.722(4) 0.6989(11) 0.039(5) Uiso 1 1 d D . . . .
N4B N 0.33125(5) 1.2795(2) 0.55329(7) 0.0249(3) Uani 1 1 d . . . . .
N5B N 0.35342(5) 1.0976(2) 0.61825(7) 0.0256(3) Uani 1 1 d . . . . .
N6B N 0.41108(5) 1.1218(2) 0.64990(7) 0.0265(3) Uani 1 1 d . . . . .
N7B N 0.42816(5) 1.3210(2) 0.60622(7) 0.0263(3) Uani 1 1 d . . . . .
N8B N 0.37401(5) 1.6265(2) 0.48632(7) 0.0251(3) Uani 1 1 d . . . . .
C1B C 0.32484(5) 0.6008(3) 0.74706(8) 0.0208(3) Uani 1 1 d . . . . .
C2B C 0.38483(5) 0.6140(3) 0.76830(8) 0.0214(3) Uani 1 1 d . . . . .
H2B H 0.407162 0.741697 0.748063 0.026 Uiso 1 1 calc R U . . .
C3B C 0.46547(6) 0.3283(3) 0.86818(10) 0.0318(3) Uani 1 1 d . . . . .
H3F H 0.481553 0.252781 0.822650 0.048 Uiso 1 1 calc R U . . .
H3G H 0.467440 0.194556 0.915358 0.048 Uiso 1 1 calc R U . . .
H3H H 0.488231 0.485902 0.896088 0.048 Uiso 1 1 calc R U . . .
C4B C 0.37816(5) 1.4085(3) 0.54896(8) 0.0202(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
O1A C1A 1.3525(15) . ?
O1A N2A 1.3863(14) . ?
O2A N8A 1.2272(16) . ?
O3A N8A 1.2185(16) . ?
N1A N2A 1.2949(16) . ?
N1A C2A 1.3411(17) . ?
N1A C3A 1.4687(16) . ?
N3A C1A 1.3095(18) . ?
N3A H3D 0.868(14) . ?
N3A H3E 0.861(13) . ?
N4A C4A 1.3189(17) . ?
N4A N5A 1.3352(16) . ?
N5A N6A 1.3236(16) . ?
N6A N7A 1.3408(17) . ?
N7A C4A 1.3240(17) . ?
N8A C4A 1.4422(17) . ?
C1A C2A 1.3800(18) . ?
C2A H2A 0.9500 . ?
C3A H3A 0.9800 . ?
C3A H3B 0.9800 . ?
C3A H3C 0.9800 . ?
O1B C1B 1.3516(15) . ?
O1B N2B 1.3856(14) . ?
O2B N8B 1.2263(15) . ?
O3B N8B 1.2192(15) . ?
N1B N2B 1.2973(16) . ?
N1B C2B 1.3403(17) . ?
N1B C3B 1.4653(17) . ?
N3B C1B 1.3082(18) . ?
N3B H3I 0.858(13) . ?
N3B H3J 0.869(14) . ?
N4B C4B 1.3217(17) . ?
N4B N5B 1.3360(16) . ?
N5B N6B 1.3256(16) . ?
N6B N7B 1.3396(16) . ?
N7B C4B 1.3250(17) . ?
N8B C4B 1.4416(17) . ?
C1B C2B 1.3799(18) . ?
C2B H2B 0.9500 . ?
C3B H3F 0.9800 . ?
C3B H3G 0.9800 . ?
C3B H3H 0.9800 . ?

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
C1A O1A N2A 109.54(9) . . ?
N2A N1A C2A 115.05(10) . . ?
N2A N1A C3A 118.17(11) . . ?
C2A N1A C3A 126.76(11) . . ?
N1A N2A O1A 103.87(9) . . ?
C1A N3A H3D 121.4(11) . . ?
C1A N3A H3E 115.0(11) . . ?
H3D N3A H3E 122.7(16) . . ?
C4A N4A N5A 103.09(10) . . ?
N6A N5A N4A 109.73(10) . . ?
N5A N6A N7A 109.71(10) . . ?
C4A N7A N6A 102.68(11) . . ?
O3A N8A O2A 124.94(12) . . ?
O3A N8A C4A 117.72(12) . . ?
O2A N8A C4A 117.34(11) . . ?
N3A C1A O1A 119.34(11) . . ?
N3A C1A C2A 133.48(12) . . ?
O1A C1A C2A 107.17(11) . . ?
N1A C2A C1A 104.34(11) . . ?
N1A C2A H2A 127.8 . . ?
C1A C2A H2A 127.8 . . ?
N1A C3A H3A 109.5 . . ?
N1A C3A H3B 109.5 . . ?
H3A C3A H3B 109.5 . . ?
N1A C3A H3C 109.5 . . ?
H3A C3A H3C 109.5 . . ?
H3B C3A H3C 109.5 . . ?
N4A C4A N7A 114.79(11) . . ?
N4A C4A N8A 121.59(11) . . ?
N7A C4A N8A 123.61(12) . . ?
C1B O1B N2B 109.54(9) . . ?
N2B N1B C2B 115.06(11) . . ?
N2B N1B C3B 117.79(11) . . ?
C2B N1B C3B 127.14(11) . . ?
N1B N2B O1B 103.83(9) . . ?
C1B N3B H3I 115.5(11) . . ?
C1B N3B H3J 119.8(12) . . ?
H3I N3B H3J 124.4(16) . . ?
C4B N4B N5B 103.01(10) . . ?
N6B N5B N4B 109.84(10) . . ?
N5B N6B N7B 109.59(10) . . ?
C4B N7B N6B 102.90(10) . . ?
O3B N8B O2B 124.76(12) . . ?
O3B N8B C4B 117.79(11) . . ?
O2B N8B C4B 117.45(11) . . ?
N3B C1B O1B 118.97(11) . . ?
N3B C1B C2B 133.73(12) . . ?
O1B C1B C2B 107.29(11) . . ?
N1B C2B C1B 104.28(11) . . ?
N1B C2B H2B 127.9 . . ?
C1B C2B H2B 127.9 . . ?
N1B C3B H3F 109.5 . . ?
N1B C3B H3G 109.5 . . ?
H3F C3B H3G 109.5 . . ?
N1B C3B H3H 109.5 . . ?
H3F C3B H3H 109.5 . . ?
H3G C3B H3H 109.5 . . ?
N4B C4B N7B 114.67(11) . . ?
N4B C4B N8B 121.63(11) . . ?
N7B C4B N8B 123.70(11) . . ?

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
C2A N1A N2A O1A -0.51(13) . . . . ?
C3A N1A N2A O1A -178.95(10) . . . . ?
C1A O1A N2A N1A 1.10(12) . . . . ?
C4A N4A N5A N6A 0.01(13) . . . . ?
N4A N5A N6A N7A -0.07(14) . . . . ?
N5A N6A N7A C4A 0.10(13) . . . . ?
N2A O1A C1A N3A 179.05(11) . . . . ?
N2A O1A C1A C2A -1.28(12) . . . . ?
N2A N1A C2A C1A -0.25(14) . . . . ?
C3A N1A C2A C1A 178.04(11) . . . . ?
N3A C1A C2A N1A -179.47(13) . . . . ?
O1A C1A C2A N1A 0.92(13) . . . . ?
N5A N4A C4A N7A 0.06(14) . . . . ?
N5A N4A C4A N8A 179.87(11) . . . . ?
N6A N7A C4A N4A -0.10(14) . . . . ?
N6A N7A C4A N8A -179.91(11) . . . . ?
O3A N8A C4A N4A 4.43(17) . . . . ?
O2A N8A C4A N4A -174.56(12) . . . . ?
O3A N8A C4A N7A -175.77(12) . . . . ?
O2A N8A C4A N7A 5.24(18) . . . . ?
C2B N1B N2B O1B 0.37(13) . . . . ?
C3B N1B N2B O1B 179.56(10) . . . . ?
C1B O1B N2B N1B -0.84(12) . . . . ?
C4B N4B N5B N6B -0.05(13) . . . . ?
N4B N5B N6B N7B -0.04(14) . . . . ?
N5B N6B N7B C4B 0.10(13) . . . . ?
N2B O1B C1B N3B -179.34(11) . . . . ?
N2B O1B C1B C2B 0.99(13) . . . . ?
N2B N1B C2B C1B 0.21(14) . . . . ?
C3B N1B C2B C1B -178.88(12) . . . . ?
N3B C1B C2B N1B 179.67(14) . . . . ?
O1B C1B C2B N1B -0.73(13) . . . . ?
N5B N4B C4B N7B 0.12(14) . . . . ?
N5B N4B C4B N8B -179.84(10) . . . . ?
N6B N7B C4B N4B -0.14(14) . . . . ?
N6B N7B C4B N8B 179.82(11) . . . . ?
O3B N8B C4B N4B 3.85(17) . . . . ?
O2B N8B C4B N4B -175.48(11) . . . . ?
O3B N8B C4B N7B -176.11(11) . . . . ?
O2B N8B C4B N7B 4.56(18) . . . . ?

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
N3A H3D N4B 0.868(14) 2.055(14) 2.9186(16) 173.4(16) . yes
N3A H3E N5A 0.861(13) 2.140(14) 2.9498(16) 156.5(15) 4_585 yes
C2A H2A N6A 0.95 2.48 3.3273(17) 148.2 4_585 yes
C3A H3A N6A 0.98 2.70 3.3491(17) 124.2 4_575 yes
C3A H3B N7A 0.98 2.63 3.5140(19) 149.4 3_576 yes
C3A H3C O2A 0.98 2.61 3.5121(19) 153.8 . yes
N3B H3I N5B 0.858(13) 2.181(14) 2.9759(16) 154.0(15) . yes
N3B H3J N4A 0.869(14) 2.058(14) 2.9207(16) 171.6(16) . yes
C2B H2B N5B 0.95 2.69 3.2722(16) 120.1 . yes
C2B H2B N6B 0.95 2.45 3.3079(17) 149.5 . yes
C3B H3H N7B 0.98 2.63 3.4890(19) 146.3 2_646 yes

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_G117E_MSI_CLO4_0m
_database_code_depnum_ccdc_archive 'CCDC 2024996'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2021-01-11 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         'C3 H6 N3 O, Cl O4'
_chemical_formula_sum            'C3 H6 Cl N3 O5'
_chemical_formula_weight         199.56

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.5213(6)
_cell_length_b                   5.18440(10)
_cell_length_c                   14.8287(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.6857(11)
_cell_angle_gamma                90
_cell_volume                     1451.73(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.8402
_cell_measurement_theta_max      33.1505

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.517
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6772
_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            18329
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         33.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2673
_reflns_number_gt                2415
_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          
;
Positions of N-H 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)+(0.0336P)²+1.1237P] 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       0.0056(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2673
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.37449(5) 0.33309(18) 0.38989(6) 0.01651(16) Uani 1 1 d . . . . .
H1 H 0.408239 0.207815 0.419566 0.020 Uiso 1 1 calc R U . . .
C2 C 0.30172(5) 0.32790(18) 0.37751(6) 0.01517(16) Uani 1 1 d . . . . .
C3 C 0.45480(5) 0.6624(2) 0.34430(7) 0.01991(18) Uani 1 1 d . . . . .
H3A H 0.482925 0.526370 0.325017 0.030 Uiso 1 1 calc R U . . .
H3B H 0.480282 0.729143 0.405435 0.030 Uiso 1 1 calc R U . . .
H3C H 0.446867 0.802625 0.298490 0.030 Uiso 1 1 calc R U . . .
N1 N 0.33018(4) 0.69184(17) 0.31466(6) 0.01973(16) Uani 1 1 d . . . . .
N2 N 0.38632(4) 0.55619(16) 0.35022(5) 0.01531(14) Uani 1 1 d . . . . .
N3 N 0.25701(5) 0.16369(17) 0.39905(6) 0.01923(16) Uani 1 1 d . . . . .
H3D H 0.2152(8) 0.196(3) 0.3890(10) 0.023 Uiso 1 1 d . U . . .
H3E H 0.2735(8) 0.037(3) 0.4310(10) 0.023 Uiso 1 1 d . U . . .
O1 O 0.27542(4) 0.54576(14) 0.33165(5) 0.01915(14) Uani 1 1 d . . . . .
O2 O 0.40655(5) 0.27309(19) 0.18218(6) 0.0329(2) Uani 1 1 d . . . . .
O3 O 0.38568(4) -0.13420(15) 0.11009(6) 0.02573(17) Uani 1 1 d . . . . .
O4 O 0.32859(4) 0.23462(16) 0.03326(5) 0.02487(16) Uani 1 1 d . . . . .
O5 O 0.45103(4) 0.17659(17) 0.05259(6) 0.02617(17) Uani 1 1 d . . . . .
Cl1 Cl 0.39316(2) 0.13921(4) 0.09537(2) 0.01512(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 N2 1.3439(12) . ?
C1 C2 1.3858(12) . ?
C1 H1 0.9500 . ?
C2 N3 1.3151(12) . ?
C2 O1 1.3508(11) . ?
C3 N2 1.4688(12) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N1 N2 1.2964(11) . ?
N1 O1 1.3843(11) . ?
N3 H3D 0.809(16) . ?
N3 H3E 0.825(16) . ?
O2 Cl1 1.4271(8) . ?
O3 Cl1 1.4472(8) . ?
O4 Cl1 1.4468(7) . ?
O5 Cl1 1.4422(7) . ?

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 C2 104.06(8) . . ?
N2 C1 H1 128.0 . . ?
C2 C1 H1 128.0 . . ?
N3 C2 O1 118.20(8) . . ?
N3 C2 C1 134.55(9) . . ?
O1 C2 C1 107.24(8) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 N1 O1 103.97(7) . . ?
N1 N2 C1 115.06(8) . . ?
N1 N2 C3 117.43(8) . . ?
C1 N2 C3 127.50(8) . . ?
C2 N3 H3D 121.4(11) . . ?
C2 N3 H3E 117.9(10) . . ?
H3D N3 H3E 119.8(14) . . ?
C2 O1 N1 109.67(7) . . ?
O2 Cl1 O5 110.29(5) . . ?
O2 Cl1 O4 109.80(5) . . ?
O5 Cl1 O4 109.10(5) . . ?
O2 Cl1 O3 110.04(6) . . ?
O5 Cl1 O3 108.55(5) . . ?
O4 Cl1 O3 109.02(5) . . ?

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 C2 N3 179.16(10) . . . . ?
N2 C1 C2 O1 0.11(9) . . . . ?
O1 N1 N2 C1 -0.28(10) . . . . ?
O1 N1 N2 C3 -179.35(7) . . . . ?
C2 C1 N2 N1 0.11(10) . . . . ?
C2 C1 N2 C3 179.08(8) . . . . ?
N3 C2 O1 N1 -179.51(8) . . . . ?
C1 C2 O1 N1 -0.28(10) . . . . ?
N2 N1 O1 C2 0.33(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3A O2 0.98 2.61 3.0971(13) 110.6 . yes
C3 H3A O2 0.98 2.55 3.4776(14) 157.7 2_655 yes
C3 H3A O5 0.98 2.66 3.2613(14) 120.2 2_655 yes
C3 H3B O5 0.98 2.44 3.2182(12) 135.9 6_566 yes
N3 H3D O3 0.809(16) 2.160(16) 2.9470(12) 164.2(14) 4 yes
N3 H3E O4 0.825(16) 2.149(16) 2.9610(12) 168.3(14) 6_556 yes

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_G117c3_MSI_NO2BF4_0m
_database_code_depnum_ccdc_archive 'CCDC 2025852'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-09-23 deposited with the CCDC.	2021-01-11 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         ?
_chemical_formula_sum            'C3 H4 N4 O2'
_chemical_formula_weight         128.10

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      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

_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+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   6.1158(7)
_cell_length_b                   9.1928(9)
_cell_length_c                   9.3984(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     528.39(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3960
_cell_measurement_theta_min      4.0027
_cell_measurement_theta_max      33.1430

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6304
_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            4289
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.002
_diffrn_reflns_theta_max         33.198
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1077
_reflns_number_gt                989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.992

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_chemical_absolute_configuration ukn
_refine_ls_number_reflns         1077
_refine_ls_number_parameters     56
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.000000 0.72558(15) -0.12018(15) 0.0265(3) Uani 1 2 d S T P . .
O2 O 0.000000 0.25532(16) -0.0167(2) 0.0333(4) Uani 1 2 d S T P . .
N1 N 0.000000 0.85694(18) -0.05157(17) 0.0263(4) Uani 1 2 d S T P . .
N2 N 0.000000 0.82298(15) 0.08329(16) 0.0217(3) Uani 1 2 d S T P . .
N3 N 0.000000 0.48009(19) -0.07896(16) 0.0259(4) Uani 1 2 d S T P . .
N4 N 0.000000 0.38404(18) 0.0260(2) 0.0267(3) Uani 1 2 d S T P . .
C1 C 0.000000 0.9418(2) 0.1867(2) 0.0292(4) Uani 1 2 d S T P . .
H1A H -0.144379 0.948728 0.231439 0.044 Uiso 0.5 1 calc R U P . .
H1B H 0.033664 1.033517 0.138201 0.044 Uiso 0.5 1 calc R U P . .
H1C H 0.110714 0.922947 0.259789 0.044 Uiso 0.5 1 calc R U P . .
C5 C 0.000000 0.6148(2) -0.02386(17) 0.0212(3) Uani 1 2 d S T P . .
C6 C 0.000000 0.67869(18) 0.10978(19) 0.0216(4) Uani 1 2 d S T P . .
H6 H 0.000000 0.631530 0.199718 0.026 Uiso 1 2 calc R U P . .


_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 C5 1.363(2) . ?
O1 N1 1.369(2) . ?
O2 N4 1.250(2) . ?
N1 N2 1.305(2) . ?
N2 C6 1.350(2) . ?
N2 C1 1.462(2) . ?
N3 N4 1.324(2) . ?
N3 C5 1.342(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1A 0.980(13) 4 ?
C1 H1B 0.980(10) 4 ?
C1 H1C 0.98(2) 4 ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?

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
C5 O1 N1 110.26(14) . . ?
N2 N1 O1 104.27(14) . . ?
N1 N2 C6 114.46(15) . . ?
N1 N2 C1 117.82(15) . . ?
C6 N2 C1 127.72(16) . . ?
N4 N3 C5 109.13(15) . . ?
O2 N4 N3 113.08(19) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C1 H1A 109.5(3) . 4 ?
H1A C1 H1A 128.6 . 4 ?
H1B C1 H1A 87.4 . 4 ?
H1C C1 H1A 24.3 . 4 ?
N2 C1 H1B 109.5(2) . 4 ?
H1A C1 H1B 87.4 . 4 ?
H1B C1 H1B 24.3 . 4 ?
H1C C1 H1B 128.6 . 4 ?
H1A C1 H1B 109.5 4 4 ?
N2 C1 H1C 109.5(5) . 4 ?
H1A C1 H1C 24.3 . 4 ?
H1B C1 H1C 128.6 . 4 ?
H1C C1 H1C 87.4 . 4 ?
H1A C1 H1C 109.5 4 4 ?
H1B C1 H1C 109.5 4 4 ?
N3 C5 O1 115.67(16) . . ?
N3 C5 C6 137.76(18) . . ?
O1 C5 C6 106.58(15) . . ?
N2 C6 C5 104.43(16) . . ?
N2 C6 H6 127.8 . . ?
C5 C6 H6 127.8 . . ?

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
C5 O1 N1 N2 0.000(0) . . . . ?
O1 N1 N2 C6 0.000(0) . . . . ?
O1 N1 N2 C1 180.000(0) . . . . ?
C5 N3 N4 O2 180.000(0) . . . . ?
N4 N3 C5 O1 180.000(0) . . . . ?
N4 N3 C5 C6 0.000(0) . . . . ?
N1 O1 C5 N3 180.000(0) . . . . ?
N1 O1 C5 C6 0.000(0) . . . . ?
N1 N2 C6 C5 0.000(0) . . . . ?
C1 N2 C6 C5 180.000(0) . . . . ?
N3 C5 C6 N2 180.000(0) . . . . ?
O1 C5 C6 N2 0.000(0) . . . . ?

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
C1 H1B O2 0.98 2.51 3.458(3) 161.7 1_565 yes
C6 H6 N3 0.95 2.32 3.269(2) 179.1 2_565 yes

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_G117d_MSI_TAZ_0m
_database_code_depnum_ccdc_archive 'CCDC 2025853'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-08-27 deposited with the CCDC.	2021-01-11 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         'C N7, C3 H6 N3 O'
_chemical_formula_sum            'C4 H6 N10 O'
_chemical_formula_weight         210.19

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                   8.4296(13)
_cell_length_b                   5.5977(9)
_cell_length_c                   19.058(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.392(10)
_cell_angle_gamma                90
_cell_volume                     893.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    719
_cell_measurement_theta_min      5.5315
_cell_measurement_theta_max      58.1571

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.073
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5020
_exptl_absorpt_correction_T_max  0.7536
_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 diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            7434
_diffrn_reflns_av_unetI/netI     0.1856
_diffrn_reflns_av_R_equivalents  0.1817
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         5.531
_diffrn_reflns_theta_max         72.234
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1744
_reflns_number_gt                735
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1226P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1744
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1868
_refine_ls_R_factor_gt           0.0915
_refine_ls_wR_factor_ref         0.3006
_refine_ls_wR_factor_gt          0.2173
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.6899(5) 0.4107(9) 0.5096(2) 0.0622(12) Uani 1 1 d . . . . .
N1 N 0.6027(5) 0.3866(10) 0.6086(2) 0.0520(12) Uani 1 1 d . . . . .
N2 N 0.5985(6) 0.2701(10) 0.5492(3) 0.0587(14) Uani 1 1 d . . . . .
N3 N 0.8367(6) 0.7528(10) 0.5179(3) 0.0641(15) Uani 1 1 d . . . . .
H3A H 0.857767 0.730234 0.474175 0.077 Uiso 1 1 calc R U . . .
H3B H 0.875772 0.878161 0.541741 0.077 Uiso 1 1 calc R U . . .
N4 N 1.0387(6) 0.7372(10) 0.2748(3) 0.0584(14) Uani 1 1 d . . . . .
N5 N 1.1048(6) 0.9085(11) 0.3191(3) 0.0623(15) Uani 1 1 d . . . . .
N6 N 1.0510(6) 0.8853(11) 0.3809(3) 0.0606(14) Uani 1 1 d . . . . .
N7 N 0.9482(6) 0.7013(10) 0.3802(3) 0.0570(14) Uani 1 1 d . . . . .
N8 N 0.8535(6) 0.4220(10) 0.2865(3) 0.0602(14) Uani 1 1 d . . . . .
N9 N 0.7881(6) 0.3111(11) 0.3319(3) 0.0589(14) Uani 1 1 d . . . . .
N10 N 0.7189(7) 0.1998(11) 0.3671(3) 0.0691(16) Uani 1 1 d . . . . .
C1 C 0.7477(7) 0.6003(13) 0.5473(3) 0.0553(15) Uani 1 1 d . . . . .
C2 C 0.6886(7) 0.5854(12) 0.6126(3) 0.0548(15) Uani 1 1 d . . . . .
H2 H 0.705933 0.693206 0.651149 0.066 Uiso 1 1 calc R U . . .
C3 C 0.5200(7) 0.2786(12) 0.6649(3) 0.0612(17) Uani 1 1 d . . . . .
H3C H 0.413256 0.226386 0.645225 0.092 Uiso 1 1 calc R U . . .
H3D H 0.510613 0.396753 0.702134 0.092 Uiso 1 1 calc R U . . .
H3E H 0.581078 0.140699 0.684732 0.092 Uiso 1 1 calc R U . . .
C4 C 0.9454(7) 0.6177(13) 0.3152(3) 0.0554(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.343(8) . ?
O1 N2 1.382(7) . ?
N1 N2 1.304(7) . ?
N1 C2 1.325(8) . ?
N1 C3 1.472(7) . ?
N3 C1 1.304(8) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C4 1.338(8) . ?
N4 N5 1.356(7) . ?
N5 N6 1.314(7) . ?
N6 N7 1.345(7) . ?
N7 C4 1.322(8) . ?
N8 N9 1.241(7) . ?
N8 C4 1.416(8) . ?
N9 N10 1.125(8) . ?
C1 C2 1.392(8) . ?
C2 H2 0.9500 . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 N2 110.4(4) . . ?
N2 N1 C2 115.5(5) . . ?
N2 N1 C3 117.3(5) . . ?
C2 N1 C3 127.1(5) . . ?
N1 N2 O1 103.1(4) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C4 N4 N5 102.9(5) . . ?
N6 N5 N4 109.2(5) . . ?
N5 N6 N7 110.7(5) . . ?
C4 N7 N6 103.0(5) . . ?
N9 N8 C4 112.6(5) . . ?
N10 N9 N8 172.6(6) . . ?
N3 C1 O1 118.6(5) . . ?
N3 C1 C2 134.7(6) . . ?
O1 C1 C2 106.6(5) . . ?
N1 C2 C1 104.3(5) . . ?
N1 C2 H2 127.8 . . ?
C1 C2 H2 127.8 . . ?
N1 C3 H3C 109.5 . . ?
N1 C3 H3D 109.5 . . ?
H3C C3 H3D 109.5 . . ?
N1 C3 H3E 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
N7 C4 N4 114.3(6) . . ?
N7 C4 N8 126.0(5) . . ?
N4 C4 N8 119.8(5) . . ?

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 N1 N2 O1 -1.0(7) . . . . ?
C3 N1 N2 O1 -177.8(5) . . . . ?
C1 O1 N2 N1 1.5(6) . . . . ?
C4 N4 N5 N6 0.0(6) . . . . ?
N4 N5 N6 N7 -0.2(7) . . . . ?
N5 N6 N7 C4 0.3(7) . . . . ?
N2 O1 C1 N3 -179.9(5) . . . . ?
N2 O1 C1 C2 -1.6(6) . . . . ?
N2 N1 C2 C1 0.0(7) . . . . ?
C3 N1 C2 C1 176.6(6) . . . . ?
N3 C1 C2 N1 178.8(7) . . . . ?
O1 C1 C2 N1 0.9(6) . . . . ?
N6 N7 C4 N4 -0.3(7) . . . . ?
N6 N7 C4 N8 -179.6(6) . . . . ?
N5 N4 C4 N7 0.2(7) . . . . ?
N5 N4 C4 N8 179.5(5) . . . . ?
N9 N8 C4 N7 -8.9(9) . . . . ?
N9 N8 C4 N4 171.9(6) . . . . ?

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 H3A N6 0.88 2.69 3.417(7) 141.4 . yes
N3 H3A N7 0.88 2.03 2.898(7) 169.1 . yes
N3 H3B N6 0.88 2.03 2.883(8) 164.4 3_776 yes
C3 H3C N10 0.98 2.63 3.365(9) 131.7 3_656 yes
C3 H3D N4 0.98 2.47 3.419(9) 162.9 4_576 yes
C3 H3D N5 0.98 2.53 3.429(9) 152.5 4_576 yes
C3 H3E N5 0.98 2.67 3.313(8) 123.4 3_766 yes

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_G117d_MSI_TAZ_EtOH_0m
_database_code_depnum_ccdc_archive 'CCDC 2035560'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2021-01-11 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         'C2 N7 O2, C3 H6 N3 O'
_chemical_formula_sum            'C5 H6 N10 O3'
_chemical_formula_weight         254.20

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2488(8)
_cell_length_b                   13.9673(14)
_cell_length_c                   14.1051(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1034.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5415
_cell_measurement_theta_min      2.8890
_cell_measurement_theta_max      30.5696

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6069
_exptl_absorpt_correction_T_max  0.7462
_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            19772
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         31.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3434
_reflns_number_gt                2584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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 Rev1146 (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)+(0.0344P)²+0.2762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(8)
_chemical_absolute_configuration ukn
_refine_ls_number_reflns         3434
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 -0.1296(3) 0.56228(12) 0.94960(12) 0.0332(4) Uani 1 1 d . . . . .
O2 O 0.7501(4) 0.95350(12) 0.40370(12) 0.0373(4) Uani 1 1 d . . . . .
O3 O 0.4686(3) 0.84396(12) 0.46206(12) 0.0330(4) Uani 1 1 d . . . . .
N1 N 0.2371(4) 0.65170(13) 0.95988(14) 0.0331(4) Uani 1 1 d . . . . .
H1A H 0.214738 0.655591 1.021592 0.040 Uiso 1 1 calc R U . . .
H1B H 0.369504 0.679452 0.933264 0.040 Uiso 1 1 calc R U . . .
N2 N -0.2753(4) 0.51637(15) 0.88088(16) 0.0360(5) Uani 1 1 d . . . . .
N3 N -0.1549(4) 0.53455(13) 0.80265(15) 0.0290(4) Uani 1 1 d . . . . .
N4 N 0.7796(4) 0.89339(12) 0.55828(13) 0.0260(4) Uani 1 1 d . . . . .
N5 N 0.6223(3) 0.83078(12) 0.59714(13) 0.0236(4) Uani 1 1 d . . . . .
N6 N 0.4369(4) 0.79859(14) 0.54701(14) 0.0319(4) Uani 1 1 d . . . . .
N7 N 0.7944(4) 0.85058(13) 0.75210(14) 0.0310(4) Uani 1 1 d . . . . .
N8 N 0.7479(4) 0.80798(13) 0.83542(13) 0.0318(4) Uani 1 1 d . . . . .
N9 N 0.5785(4) 0.73962(14) 0.82339(14) 0.0322(4) Uani 1 1 d . . . . .
N10 N 0.5076(4) 0.73465(14) 0.73228(14) 0.0323(5) Uani 1 1 d . . . . .
C1 C 0.0730(4) 0.60454(15) 0.90759(16) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.0565(4) 0.58722(15) 0.81171(17) 0.0265(4) Uani 1 1 d . . . . .
H2 H 0.169215 0.607911 0.763168 0.032 Uiso 1 1 calc R U . . .
C3 C -0.2648(5) 0.49785(19) 0.7134(2) 0.0386(6) Uani 1 1 d . . . . .
H3A H -0.425035 0.464566 0.726935 0.058 Uiso 1 1 calc R U . . .
H3B H -0.144703 0.453213 0.683759 0.058 Uiso 1 1 calc R U . . .
H3C H -0.297435 0.551426 0.670190 0.058 Uiso 1 1 calc R U . . .
C4 C 0.6861(4) 0.90443(15) 0.46992(16) 0.0261(4) Uani 1 1 d . . . . .
C5 C 0.6452(4) 0.80346(15) 0.69362(15) 0.0238(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.353(3) . ?
O1 N2 1.391(3) . ?
O2 C4 1.206(3) . ?
O3 N6 1.366(3) . ?
O3 C4 1.425(3) . ?
N1 C1 1.311(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 N3 1.297(3) . ?
N3 C2 1.338(3) . ?
N3 C3 1.477(3) . ?
N4 N5 1.322(2) . ?
N4 C4 1.348(3) . ?
N5 N6 1.284(3) . ?
N5 C5 1.418(3) . ?
N7 C5 1.314(3) . ?
N7 N8 1.340(3) . ?
N8 N9 1.315(3) . ?
N9 N10 1.340(3) . ?
N10 C5 1.320(3) . ?
C1 C2 1.377(3) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 N2 109.16(18) . . ?
N6 O3 C4 107.73(17) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N3 N2 O1 103.57(18) . . ?
N2 N3 C2 115.5(2) . . ?
N2 N3 C3 117.9(2) . . ?
C2 N3 C3 126.6(2) . . ?
N5 N4 C4 103.40(18) . . ?
N6 N5 N4 118.47(19) . . ?
N6 N5 C5 119.87(18) . . ?
N4 N5 C5 121.54(18) . . ?
N5 N6 O3 103.19(18) . . ?
C5 N7 N8 102.67(19) . . ?
N9 N8 N7 109.43(19) . . ?
N8 N9 N10 110.44(18) . . ?
C5 N10 N9 101.90(19) . . ?
N1 C1 O1 119.3(2) . . ?
N1 C1 C2 133.0(2) . . ?
O1 C1 C2 107.7(2) . . ?
N3 C2 C1 104.1(2) . . ?
N3 C2 H2 128.0 . . ?
C1 C2 H2 128.0 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N4 132.8(2) . . ?
O2 C4 O3 120.0(2) . . ?
N4 C4 O3 107.20(18) . . ?
N7 C5 N10 115.6(2) . . ?
N7 C5 N5 121.18(19) . . ?
N10 C5 N5 123.1(2) . . ?

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 O1 N2 N3 -0.7(2) . . . . ?
O1 N2 N3 C2 0.4(2) . . . . ?
O1 N2 N3 C3 -178.28(18) . . . . ?
C4 N4 N5 N6 0.0(2) . . . . ?
C4 N4 N5 C5 -176.13(18) . . . . ?
N4 N5 N6 O3 0.3(2) . . . . ?
C5 N5 N6 O3 176.48(17) . . . . ?
C4 O3 N6 N5 -0.4(2) . . . . ?
C5 N7 N8 N9 0.0(3) . . . . ?
N7 N8 N9 N10 0.0(3) . . . . ?
N8 N9 N10 C5 0.0(3) . . . . ?
N2 O1 C1 N1 -179.66(19) . . . . ?
N2 O1 C1 C2 0.9(2) . . . . ?
N2 N3 C2 C1 0.1(2) . . . . ?
C3 N3 C2 C1 178.7(2) . . . . ?
N1 C1 C2 N3 180.0(2) . . . . ?
O1 C1 C2 N3 -0.6(2) . . . . ?
N5 N4 C4 O2 178.8(2) . . . . ?
N5 N4 C4 O3 -0.2(2) . . . . ?
N6 O3 C4 O2 -178.74(19) . . . . ?
N6 O3 C4 N4 0.4(2) . . . . ?
N8 N7 C5 N10 0.0(3) . . . . ?
N8 N7 C5 N5 175.47(19) . . . . ?
N9 N10 C5 N7 0.0(3) . . . . ?
N9 N10 C5 N5 -175.4(2) . . . . ?
N6 N5 C5 N7 -164.5(2) . . . . ?
N4 N5 C5 N7 11.6(3) . . . . ?
N6 N5 C5 N10 10.6(3) . . . . ?
N4 N5 C5 N10 -173.3(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
N1 H1A N8 0.88 2.09 2.942(3) 163.7 4_467 yes
N1 H1B N9 0.88 2.08 2.903(3) 156.1 . yes
C2 H2 O2 0.95 2.54 3.254(3) 132.0 4_466 yes
C2 H2 N10 0.95 2.54 3.332(3) 140.3 . yes
C3 H3A N7 0.98 2.53 3.493(3) 168.7 3_546 yes
C3 H3B N7 0.98 2.50 3.250(3) 133.1 3_646 yes
C3 H3C O2 0.98 2.59 3.110(3) 112.9 4_366 yes

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_G117_MSI_DNTT_0m
_database_code_depnum_ccdc_archive 'CCDC 2024997'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-08-24 deposited with the CCDC.	2021-01-11 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         'C3 N7 O4, C3 H6 N3 O'
_chemical_formula_sum            'C6 H6 N10 O5'
_chemical_formula_weight         298.21

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                   7.2060(4)
_cell_length_b                   9.3911(5)
_cell_length_c                   9.4448(5)
_cell_angle_alpha                71.6516(19)
_cell_angle_beta                 85.772(2)
_cell_angle_gamma                71.196(2)
_cell_volume                     574.01(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6327
_cell_measurement_theta_min      2.7556
_cell_measurement_theta_max      33.1572

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6760
_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            19787
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         33.191
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4208
_reflns_number_gt                2910
_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          
;
The anion exhibits minor disorder in place over two alternative orientations.
The two disordered moieties were restrained to have similar geometries. 
Uij components of ADPs for disordered atoms closer to each other than 
2.0 Angstrom were restrained to be similar. Equivalent atoms in the major 
and minor moiuety were constrained to have identical ADPs. Subject to these 
conditions the occupancy ratio refined to 0.9467(10) to 0.0533(10).

Amine 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)+(0.0451P)²+0.1194P] 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       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4208
_refine_ls_number_parameters     243
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.020
_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 0.39717(18) 0.23491(14) 0.90203(13) 0.0238(2) Uani 1 1 d . . . . .
C2 C 0.53967(18) 0.20947(14) 0.79838(13) 0.0241(2) Uani 1 1 d . . . . .
H2 H 0.563608 0.136476 0.743511 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8024(2) 0.33334(19) 0.69825(17) 0.0373(3) Uani 1 1 d . . . . .
H3A H 0.754580 0.391215 0.594983 0.056 Uiso 1 1 calc R U . . .
H3B H 0.896565 0.229858 0.702665 0.056 Uiso 1 1 calc R U . . .
H3C H 0.866637 0.393606 0.733924 0.056 Uiso 1 1 calc R U . . .
N1 N 0.25846(19) 0.17317(15) 0.95677(14) 0.0315(3) Uani 1 1 d . . . . .
H1A H 0.181(3) 0.202(2) 1.022(2) 0.040(5) Uiso 1 1 d . . . . .
H1B H 0.239(3) 0.098(2) 0.925(2) 0.043(5) Uiso 1 1 d . . . . .
N2 N 0.57393(17) 0.39806(13) 0.88094(12) 0.0282(2) Uani 1 1 d . . . . .
N3 N 0.63640(16) 0.31137(12) 0.79297(11) 0.0255(2) Uani 1 1 d . . . . .
O1 O 0.41906(14) 0.34912(10) 0.95179(10) 0.0264(2) Uani 1 1 d . . . . .
C4 C 0.57851(19) 0.81021(15) 0.61133(14) 0.0216(2) Uani 0.9467(10) 1 d D . P A
1
C5 C 0.36479(19) 0.87773(14) 0.75358(13) 0.0221(2) Uani 0.9467(10) 1 d D . P A
1
C6 C 0.16908(18) 0.74095(16) 0.77790(14) 0.0215(2) Uani 0.9467(10) 1 d D . P A
1
O2 O 0.78883(16) 0.71131(13) 0.44546(13) 0.0362(2) Uani 0.9467(10) 1 d D . P A
1
O3 O 0.8487(2) 0.8872(2) 0.5241(2) 0.0313(3) Uani 0.9467(10) 1 d D . P A 1
O4 O 0.15991(15) 0.54893(12) 0.68523(11) 0.0293(2) Uani 0.9467(10) 1 d D . P A
1
O5 O -0.06586(17) 0.62040(16) 0.83931(15) 0.0302(3) Uani 0.9467(10) 1 d D . P A
1
N4 N 0.33355(16) 0.76358(14) 0.70752(13) 0.0200(2) Uani 0.9467(10) 1 d D . P A
1
N5 N 0.47352(15) 0.71643(12) 0.61130(11) 0.0218(2) Uani 0.9467(10) 1 d D . P A
1
N6 N 0.52634(17) 0.91041(14) 0.69238(13) 0.0232(2) Uani 0.9467(10) 1 d D . P A
1
N7 N 0.22537(17) 0.92463(13) 0.84734(12) 0.0261(2) Uani 0.9467(10) 1 d D . P A
1
N8 N 0.10328(17) 0.83587(14) 0.86069(13) 0.0254(2) Uani 0.9467(10) 1 d D . P A
1
N9 N 0.75137(17) 0.80184(14) 0.52034(13) 0.0251(2) Uani 0.9467(10) 1 d D . P A
1
N10 N 0.08232(17) 0.62977(14) 0.76714(12) 0.0233(2) Uani 0.9467(10) 1 d D . P A
1
C4B C 0.164(3) 0.687(2) 0.746(2) 0.0216(2) Uani 0.0533(10) 1 d D . P A 2
C5B C 0.277(3) 0.848(2) 0.785(2) 0.0221(2) Uani 0.0533(10) 1 d D . P A 2
C6B C 0.539(3) 0.844(3) 0.659(2) 0.0215(2) Uani 0.0533(10) 1 d D . P A 2
O2B O 0.087(3) 0.494(2) 0.679(2) 0.0362(2) Uani 0.0533(10) 1 d D . P A 2
O3B O -0.101(3) 0.598(4) 0.829(3) 0.0313(3) Uani 0.0533(10) 1 d D . P A 2
O4B O 0.692(3) 0.7029(19) 0.504(2) 0.0293(2) Uani 0.0533(10) 1 d D . P A 2
O5B O 0.814(5) 0.872(5) 0.537(5) 0.0302(3) Uani 0.0533(10) 1 d D . P A 2
N4B N 0.392(3) 0.775(3) 0.691(3) 0.0200(2) Uani 0.0533(10) 1 d D . P A 2
N5B N 0.324(2) 0.6682(19) 0.6599(19) 0.0218(2) Uani 0.0533(10) 1 d D . P A 2
N6B N 0.130(3) 0.787(2) 0.825(2) 0.0232(2) Uani 0.0533(10) 1 d D . P A 2
N7B N 0.353(3) 0.950(2) 0.810(2) 0.0261(2) Uani 0.0533(10) 1 d D . P A 2
N8B N 0.518(3) 0.949(3) 0.726(2) 0.0254(2) Uani 0.0533(10) 1 d D . P A 2
N9B N 0.046(3) 0.586(2) 0.753(2) 0.0251(2) Uani 0.0533(10) 1 d D . P A 2
N10B N 0.690(3) 0.802(2) 0.566(2) 0.0233(2) Uani 0.0533(10) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3081(18) . ?
C1 O1 1.3541(14) . ?
C1 C2 1.3823(17) . ?
C2 N3 1.3410(17) . ?
C2 H2 0.9500 . ?
C3 N3 1.4691(17) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N1 H1A 0.854(19) . ?
N1 H1B 0.898(19) . ?
N2 N3 1.3000(14) . ?
N2 O1 1.3897(15) . ?
C4 N5 1.3334(16) . ?
C4 N6 1.3401(16) . ?
C4 N9 1.4552(17) . ?
C5 N6 1.3427(18) . ?
C5 N7 1.3478(16) . ?
C5 N4 1.3612(16) . ?
C6 N8 1.3201(16) . ?
C6 N4 1.3597(16) . ?
C6 N10 1.4102(18) . ?
O2 N9 1.2241(15) . ?
O3 N9 1.2326(17) . ?
O4 N10 1.2328(14) . ?
O5 N10 1.2362(15) . ?
N4 N5 1.3674(14) . ?
N7 N8 1.3693(17) . ?
C4B N6B 1.330(16) . ?
C4B N5B 1.355(16) . ?
C4B N9B 1.450(15) . ?
C5B N7B 1.335(15) . ?
C5B N6B 1.336(15) . ?
C5B N4B 1.364(16) . ?
C6B N8B 1.301(16) . ?
C6B N4B 1.378(15) . ?
C6B N10B 1.381(15) . ?
O2B N9B 1.226(16) . ?
O3B N9B 1.234(17) . ?
O4B N10B 1.236(16) . ?
O5B N10B 1.240(17) . ?
N4B N5B 1.363(15) . ?
N7B N8B 1.377(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
N1 C1 O1 118.73(11) . . ?
N1 C1 C2 134.08(12) . . ?
O1 C1 C2 107.19(11) . . ?
N3 C2 C1 104.21(10) . . ?
N3 C2 H2 127.9 . . ?
C1 C2 H2 127.9 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N1 H1A 122.6(12) . . ?
C1 N1 H1B 120.9(12) . . ?
H1A N1 H1B 116.5(16) . . ?
N3 N2 O1 103.41(10) . . ?
N2 N3 C2 115.42(11) . . ?
N2 N3 C3 118.19(11) . . ?
C2 N3 C3 126.39(11) . . ?
C1 O1 N2 109.77(9) . . ?
N5 C4 N6 121.08(12) . . ?
N5 C4 N9 118.34(11) . . ?
N6 C4 N9 120.58(11) . . ?
N6 C5 N7 138.53(12) . . ?
N6 C5 N4 110.46(11) . . ?
N7 C5 N4 111.01(12) . . ?
N8 C6 N4 110.44(12) . . ?
N8 C6 N10 124.41(12) . . ?
N4 C6 N10 125.13(12) . . ?
C6 N4 C5 104.46(11) . . ?
C6 N4 N5 144.23(12) . . ?
C5 N4 N5 111.32(11) . . ?
C4 N5 N4 97.84(10) . . ?
C4 N6 C5 99.31(11) . . ?
C5 N7 N8 105.45(10) . . ?
C6 N8 N7 108.64(11) . . ?
O2 N9 O3 124.89(13) . . ?
O2 N9 C4 117.70(12) . . ?
O3 N9 C4 117.41(13) . . ?
O4 N10 O5 124.57(12) . . ?
O4 N10 C6 117.27(11) . . ?
O5 N10 C6 118.16(11) . . ?
N6B C4B N5B 120.0(14) . . ?
N6B C4B N9B 123.7(14) . . ?
N5B C4B N9B 116.2(14) . . ?
N7B C5B N6B 141.9(16) . . ?
N7B C5B N4B 109.6(13) . . ?
N6B C5B N4B 108.4(13) . . ?
N8B C6B N4B 112.3(14) . . ?
N8B C6B N10B 125.4(15) . . ?
N4B C6B N10B 122.3(15) . . ?
N5B N4B C5B 113.3(12) . . ?
N5B N4B C6B 143.1(14) . . ?
C5B N4B C6B 103.7(12) . . ?
C4B N5B N4B 96.8(12) . . ?
C4B N6B C5B 101.5(14) . . ?
C5B N7B N8B 108.3(13) . . ?
C6B N8B N7B 106.1(14) . . ?
O2B N9B O3B 120.3(19) . . ?
O2B N9B C4B 120.9(16) . . ?
O3B N9B C4B 118.7(16) . . ?
O4B N10B O5B 121(2) . . ?
O4B N10B C6B 120.0(17) . . ?
O5B N10B C6B 119.2(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N3 -179.67(14) . . . . ?
O1 C1 C2 N3 -0.31(13) . . . . ?
O1 N2 N3 C2 -0.24(13) . . . . ?
O1 N2 N3 C3 179.57(10) . . . . ?
C1 C2 N3 N2 0.36(14) . . . . ?
C1 C2 N3 C3 -179.44(12) . . . . ?
N1 C1 O1 N2 179.66(11) . . . . ?
C2 C1 O1 N2 0.19(13) . . . . ?
N3 N2 O1 C1 0.02(12) . . . . ?
N8 C6 N4 C5 0.43(14) . . . . ?
N10 C6 N4 C5 -178.33(12) . . . . ?
N8 C6 N4 N5 -179.40(17) . . . . ?
N10 C6 N4 N5 1.8(3) . . . . ?
N6 C5 N4 C6 179.40(11) . . . . ?
N7 C5 N4 C6 -0.43(14) . . . . ?
N6 C5 N4 N5 -0.71(15) . . . . ?
N7 C5 N4 N5 179.46(10) . . . . ?
N6 C4 N5 N4 -0.29(15) . . . . ?
N9 C4 N5 N4 -179.99(10) . . . . ?
C6 N4 N5 C4 -179.61(18) . . . . ?
C5 N4 N5 C4 0.56(13) . . . . ?
N5 C4 N6 C5 -0.10(15) . . . . ?
N9 C4 N6 C5 179.59(11) . . . . ?
N7 C5 N6 C4 -179.77(15) . . . . ?
N4 C5 N6 C4 0.46(13) . . . . ?
N6 C5 N7 N8 -179.49(15) . . . . ?
N4 C5 N7 N8 0.28(14) . . . . ?
N4 C6 N8 N7 -0.28(14) . . . . ?
N10 C6 N8 N7 178.50(11) . . . . ?
C5 N7 N8 C6 0.00(14) . . . . ?
N5 C4 N9 O2 1.68(17) . . . . ?
N6 C4 N9 O2 -178.02(12) . . . . ?
N5 C4 N9 O3 -178.61(14) . . . . ?
N6 C4 N9 O3 1.69(19) . . . . ?
N8 C6 N10 O4 179.98(12) . . . . ?
N4 C6 N10 O4 -1.42(19) . . . . ?
N8 C6 N10 O5 0.32(19) . . . . ?
N4 C6 N10 O5 178.92(13) . . . . ?
N7B C5B N4B N5B 180(2) . . . . ?
N6B C5B N4B N5B 2(3) . . . . ?
N7B C5B N4B C6B -1(3) . . . . ?
N6B C5B N4B C6B -179(2) . . . . ?
N8B C6B N4B N5B 178(3) . . . . ?
N10B C6B N4B N5B -2(5) . . . . ?
N8B C6B N4B C5B 0(3) . . . . ?
N10B C6B N4B C5B 180(2) . . . . ?
N6B C4B N5B N4B -1(3) . . . . ?
N9B C4B N5B N4B -177(2) . . . . ?
C5B N4B N5B C4B -1(3) . . . . ?
C6B N4B N5B C4B -179(4) . . . . ?
N5B C4B N6B C5B 2(3) . . . . ?
N9B C4B N6B C5B 178(2) . . . . ?
N7B C5B N6B C4B -179(3) . . . . ?
N4B C5B N6B C4B -3(3) . . . . ?
N6B C5B N7B N8B 179(3) . . . . ?
N4B C5B N7B N8B 3(3) . . . . ?
N4B C6B N8B N7B 2(3) . . . . ?
N10B C6B N8B N7B -178(2) . . . . ?
C5B N7B N8B C6B -2(3) . . . . ?
N6B C4B N9B O2B -179(2) . . . . ?
N5B C4B N9B O2B -3(3) . . . . ?
N6B C4B N9B O3B 4(4) . . . . ?
N5B C4B N9B O3B -180(2) . . . . ?
N8B C6B N10B O4B -178(2) . . . . ?
N4B C6B N10B O4B 3(4) . . . . ?
N8B C6B N10B O5B -3(4) . . . . ?
N4B C6B N10B O5B 177(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 N6 0.95 2.42 3.2951(17) 153.5 1_545 yes
C2 H2 N7B 0.95 2.58 3.111(15) 115.9 1_545 yes
C2 H2 N8B 0.95 1.95 2.789(18) 146.5 1_545 yes
C3 H3A O4 0.98 2.60 3.4557(18) 146.3 2_666 yes
C3 H3C O2B 0.98 2.05 2.88(2) 140.4 1_655 yes
C3 H3C O3B 0.98 2.45 3.38(2) 158.7 1_655 yes
C3 H3C N9B 0.98 2.59 3.544(16) 164.6 1_655 yes
N1 H1A O5 0.854(19) 2.342(19) 3.1010(17) 148.3(15) 2_567 yes
N1 H1A N8 0.854(19) 2.330(18) 3.0269(17) 139.1(15) 2_567 yes
N1 H1A O3B 0.854(19) 2.58(3) 3.29(2) 141.3(16) 2_567 yes
N1 H1A N6B 0.854(19) 2.56(3) 3.342(17) 152.5(16) 2_567 yes
N1 H1B N7 0.898(19) 2.02(2) 2.9131(16) 173.9(17) 1_545 yes
N1 H1B N7B 0.898(19) 1.97(2) 2.748(15) 144.0(17) 1_545 yes

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051



