# 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 2019

####################################################################### 
# 
# 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_shrv355
_database_code_depnum_ccdc_archive 'CCDC 1915165'
loop_
_audit_author_name
_audit_author_address
'Lauren A. Mitchell'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H N9 O2, H2 O'
_chemical_formula_sum            'C3 H3 N9 O3'
_chemical_formula_weight         213.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0066(6)
_cell_length_b                   6.2343(4)
_cell_length_c                   13.5638(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.909(2)
_cell_angle_gamma                90
_cell_volume                     805.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2245
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      26.40

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.047
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6840
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7404
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.157
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1645
_reflns_number_gt                1284
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0429P)²+0.1659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1645
_refine_ls_number_parameters     145
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.041
_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 0.11540(11) 0.68754(17) 0.51819(8) 0.0260(3) Uani 1 1 d D . . . .
H1 H 0.0523(16) 0.737(3) 0.5416(14) 0.039 Uiso 1 1 d D U . . .
N2 N 0.20866(12) 0.58591(19) 0.59857(9) 0.0186(3) Uani 1 1 d . . . . .
N3 N 0.17998(13) 0.3981(2) 0.63487(9) 0.0239(3) Uani 1 1 d . . . . .
N4 N 0.29380(13) 0.34722(19) 0.70876(9) 0.0234(3) Uani 1 1 d . . . . .
N5 N 0.39499(12) 0.49803(18) 0.71981(9) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.33969(14) 0.6468(2) 0.64990(10) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.40744(14) 0.8445(2) 0.63456(11) 0.0171(3) Uani 1 1 d . . . . .
N8 N 0.35373(13) 0.97784(19) 0.55855(10) 0.0217(3) Uani 1 1 d . . . . .
O9 O 0.44947(11) 1.14267(16) 0.57267(8) 0.0253(3) Uani 1 1 d . . . . .
N10 N 0.56440(13) 1.1085(2) 0.65973(10) 0.0236(3) Uani 1 1 d . . . . .
C11 C 0.53865(14) 0.9271(2) 0.69807(11) 0.0184(3) Uani 1 1 d . . . . .
N12 N 0.62425(13) 0.82621(19) 0.78635(9) 0.0230(3) Uani 1 1 d . . . . .
N13 N 0.72375(13) 0.94100(19) 0.84045(9) 0.0216(3) Uani 1 1 d . . . . .
N14 N 0.81621(14) 1.0199(2) 0.89680(11) 0.0296(3) Uani 1 1 d . . . . .
O1S O 0.57340(12) 0.34179(17) 0.90969(9) 0.0277(3) Uani 1 1 d D . . . .
H1S H 0.6340(15) 0.418(3) 0.9442(12) 0.041 Uiso 1 1 d D U . . .
H2S H 0.5431(17) 0.425(3) 0.8631(10) 0.041 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.3547(15) . ?
O1 H1 0.847(9) . ?
N2 N3 1.3355(17) . ?
N2 C6 1.3366(18) . ?
N3 N4 1.3039(17) . ?
N4 N5 1.3558(16) . ?
N5 C6 1.3203(17) . ?
C6 C7 1.4520(18) . ?
C7 N8 1.3047(18) . ?
C7 C11 1.427(2) . ?
N8 O9 1.3776(15) . ?
O9 N10 1.3883(16) . ?
N10 C11 1.3027(19) . ?
C11 N12 1.3902(18) . ?
N12 N13 1.2620(17) . ?
N13 N14 1.1168(17) . ?
O1S H1S 0.797(9) . ?
O1S H2S 0.802(9) . ?

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 O1 H1 106.1(13) . . ?
N3 N2 C6 110.16(11) . . ?
N3 N2 O1 122.27(11) . . ?
C6 N2 O1 127.51(12) . . ?
N4 N3 N2 105.10(11) . . ?
N3 N4 N5 111.26(11) . . ?
C6 N5 N4 105.90(11) . . ?
N5 C6 N2 107.57(12) . . ?
N5 C6 C7 126.02(13) . . ?
N2 C6 C7 126.37(13) . . ?
N8 C7 C11 109.02(12) . . ?
N8 C7 C6 123.85(13) . . ?
C11 C7 C6 127.13(13) . . ?
C7 N8 O9 105.40(11) . . ?
N8 O9 N10 111.25(10) . . ?
C11 N10 O9 105.01(11) . . ?
N10 C11 N12 126.26(13) . . ?
N10 C11 C7 109.31(12) . . ?
N12 C11 C7 124.43(12) . . ?
N13 N12 C11 114.28(12) . . ?
N14 N13 N12 170.80(15) . . ?
H1S O1S H2S 96.5(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 N4 0.52(15) . . . . ?
O1 N2 N3 N4 178.13(11) . . . . ?
N2 N3 N4 N5 -0.49(14) . . . . ?
N3 N4 N5 C6 0.29(15) . . . . ?
N4 N5 C6 N2 0.05(14) . . . . ?
N4 N5 C6 C7 177.88(12) . . . . ?
N3 N2 C6 N5 -0.36(15) . . . . ?
O1 N2 C6 N5 -177.81(12) . . . . ?
N3 N2 C6 C7 -178.18(12) . . . . ?
O1 N2 C6 C7 4.4(2) . . . . ?
N5 C6 C7 N8 173.60(13) . . . . ?
N2 C6 C7 N8 -9.0(2) . . . . ?
N5 C6 C7 C11 -7.4(2) . . . . ?
N2 C6 C7 C11 170.02(13) . . . . ?
C11 C7 N8 O9 0.42(14) . . . . ?
C6 C7 N8 O9 179.56(12) . . . . ?
C7 N8 O9 N10 -0.07(14) . . . . ?
N8 O9 N10 C11 -0.34(14) . . . . ?
O9 N10 C11 N12 -179.83(12) . . . . ?
O9 N10 C11 C7 0.59(14) . . . . ?
N8 C7 C11 N10 -0.67(16) . . . . ?
C6 C7 C11 N10 -179.78(13) . . . . ?
N8 C7 C11 N12 179.74(13) . . . . ?
C6 C7 C11 N12 0.6(2) . . . . ?
N10 C11 N12 N13 11.3(2) . . . . ?
C7 C11 N12 N13 -169.13(12) . . . . ?

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
O1 H1 O1S 0.847(9) 1.719(10) 2.5666(15) 179(2) 2_556
O1S H1S N8 0.797(9) 2.360(10) 3.1188(16) 159.5(18) 4_676
O1S H2S N5 0.802(9) 2.100(11) 2.8181(16) 149.1(16) .

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_shrv356
_database_code_depnum_ccdc_archive 'CCDC 1915166'
loop_
_audit_author_name
_audit_author_address
'Lauren A. Mitchell'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_shrv356             
;
PROBLEM: Short Inter D...A Contact  N3       ..N13      .       2.90 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
# Added during the CSD deposition process: Monday 15 July 2019 06:04 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 N9 O2, H4 N'
_chemical_formula_sum            'C3 H4 N10 O2'
_chemical_formula_weight         212.16

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

_cell_length_a                   4.7561(5)
_cell_length_b                   12.1040(12)
_cell_length_c                   14.0172(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     806.94(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4003
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7983
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.906
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1849
_reflns_number_gt                1755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     1.000
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0325P)²+0.2522P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_refine_ls_number_reflns         1849
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_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 1.0222(2) 0.68529(9) 0.39512(8) 0.0171(3) Uani 1 1 d . . . . .
N2 N 1.0492(3) 0.59731(11) 0.33985(9) 0.0139(3) Uani 1 1 d . . . . .
N3 N 1.2499(3) 0.58980(12) 0.27316(10) 0.0169(3) Uani 1 1 d . . . . .
N4 N 1.2186(3) 0.49163(12) 0.23360(10) 0.0172(3) Uani 1 1 d . . . . .
N5 N 1.0026(3) 0.43582(12) 0.27288(9) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.8996(3) 0.50308(13) 0.34008(11) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.6739(3) 0.47703(13) 0.40560(11) 0.0143(3) Uani 1 1 d . . . . .
N8 N 0.5783(3) 0.54455(12) 0.47081(10) 0.0179(3) Uani 1 1 d . . . . .
O9 O 0.3619(3) 0.48822(10) 0.51575(8) 0.0196(3) Uani 1 1 d . . . . .
N10 N 0.3263(3) 0.38330(12) 0.47711(10) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.5167(3) 0.37633(13) 0.41014(11) 0.0153(3) Uani 1 1 d . . . . .
N12 N 0.5644(3) 0.28690(12) 0.35025(10) 0.0201(3) Uani 1 1 d . . . . .
N13 N 0.4058(3) 0.20573(12) 0.36491(10) 0.0196(3) Uani 1 1 d . . . . .
N14 N 0.2853(4) 0.12643(14) 0.36821(12) 0.0301(4) Uani 1 1 d . . . . .
N2S N 0.5294(3) 0.81771(13) 0.39423(10) 0.0164(3) Uani 1 1 d . . . . .
H1S H 0.369(5) 0.7813(17) 0.3762(14) 0.020 Uiso 1 1 d . U . . .
H2S H 0.681(5) 0.7678(17) 0.3869(15) 0.020 Uiso 1 1 d . U . . .
H3S H 0.564(5) 0.8765(18) 0.3593(14) 0.020 Uiso 1 1 d . U . . .
H4S H 0.525(4) 0.8380(17) 0.4548(15) 0.020 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.3232(17) . ?
N2 N3 1.3391(19) . ?
N2 C6 1.344(2) . ?
N3 N4 1.320(2) . ?
N4 N5 1.347(2) . ?
N5 C6 1.338(2) . ?
C6 C7 1.447(2) . ?
C7 N8 1.308(2) . ?
C7 C11 1.431(2) . ?
N8 O9 1.3858(19) . ?
O9 N10 1.3910(18) . ?
N10 C11 1.307(2) . ?
C11 N12 1.389(2) . ?
N12 N13 1.256(2) . ?
N13 N14 1.119(2) . ?
N2S H1S 0.92(2) . ?
N2S H2S 0.95(2) . ?
N2S H3S 0.88(2) . ?
N2S H4S 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N2 N3 122.18(13) . . ?
O1 N2 C6 129.06(13) . . ?
N3 N2 C6 108.74(13) . . ?
N4 N3 N2 105.91(13) . . ?
N3 N4 N5 111.46(13) . . ?
C6 N5 N4 105.18(13) . . ?
N5 C6 N2 108.71(14) . . ?
N5 C6 C7 125.85(14) . . ?
N2 C6 C7 125.37(14) . . ?
N8 C7 C11 108.62(15) . . ?
N8 C7 C6 124.42(15) . . ?
C11 C7 C6 126.95(14) . . ?
C7 N8 O9 105.57(13) . . ?
N8 O9 N10 111.27(12) . . ?
C11 N10 O9 104.72(13) . . ?
N10 C11 N12 126.71(15) . . ?
N10 C11 C7 109.81(14) . . ?
N12 C11 C7 123.48(14) . . ?
N13 N12 C11 114.38(14) . . ?
N14 N13 N12 170.30(17) . . ?
H1S N2S H2S 107.3(17) . . ?
H1S N2S H3S 113.1(19) . . ?
H2S N2S H3S 108.2(19) . . ?
H1S N2S H4S 112.4(19) . . ?
H2S N2S H4S 107.4(18) . . ?
H3S N2S H4S 108.3(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 N3 N4 178.77(13) . . . . ?
C6 N2 N3 N4 0.31(17) . . . . ?
N2 N3 N4 N5 0.15(17) . . . . ?
N3 N4 N5 C6 -0.54(17) . . . . ?
N4 N5 C6 N2 0.72(17) . . . . ?
N4 N5 C6 C7 -176.41(15) . . . . ?
O1 N2 C6 N5 -178.98(14) . . . . ?
N3 N2 C6 N5 -0.66(18) . . . . ?
O1 N2 C6 C7 -1.8(3) . . . . ?
N3 N2 C6 C7 176.49(14) . . . . ?
N5 C6 C7 N8 179.79(16) . . . . ?
N2 C6 C7 N8 3.1(3) . . . . ?
N5 C6 C7 C11 -1.0(3) . . . . ?
N2 C6 C7 C11 -177.67(16) . . . . ?
C11 C7 N8 O9 -0.47(17) . . . . ?
C6 C7 N8 O9 178.86(14) . . . . ?
C7 N8 O9 N10 0.36(17) . . . . ?
N8 O9 N10 C11 -0.08(17) . . . . ?
O9 N10 C11 N12 -179.59(15) . . . . ?
O9 N10 C11 C7 -0.21(17) . . . . ?
N8 C7 C11 N10 0.45(19) . . . . ?
C6 C7 C11 N10 -178.86(15) . . . . ?
N8 C7 C11 N12 179.85(15) . . . . ?
C6 C7 C11 N12 0.5(3) . . . . ?
N10 C11 N12 N13 -0.7(3) . . . . ?
C7 C11 N12 N13 179.96(15) . . . . ?

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
N2S H1S O1 0.92(2) 2.04(2) 2.896(2) 155.9(18) 1_455
N2S H2S O1 0.95(2) 1.91(2) 2.8395(19) 167.2(19) .
N2S H3S N4 0.88(2) 2.17(2) 3.013(2) 161(2) 3_755
N2S H4S O1 0.88(2) 2.12(2) 2.9531(18) 156.2(19) 2_466

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_shrv353
_database_code_depnum_ccdc_archive 'CCDC 1915167'
loop_
_audit_author_name
_audit_author_address
'Lauren A. Mitchell'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 N9 O2, H4 N O'
_chemical_formula_sum            'C3 H4 N10 O3'
_chemical_formula_weight         228.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.1410(6)
_cell_length_b                   4.7291(2)
_cell_length_c                   15.1338(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.803(2)
_cell_angle_gamma                90
_cell_volume                     843.83(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4607
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.58

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.687
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.7065
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8170
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.772
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1936
_reflns_number_gt                1804
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0395P)²+0.4795P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.18258(8) 0.01902(19) 0.40442(6) 0.0174(2) Uani 1 1 d . . . . .
N2 N 0.16147(8) -0.0373(2) 0.48357(7) 0.0132(2) Uani 1 1 d . . . . .
N3 N 0.08835(9) -0.2410(2) 0.49313(7) 0.0162(2) Uani 1 1 d . . . . .
N4 N 0.08847(9) -0.2432(2) 0.57994(7) 0.0162(2) Uani 1 1 d . . . . .
N5 N 0.15911(9) -0.0478(2) 0.62671(7) 0.0156(2) Uani 1 1 d . . . . .
C6 C 0.20530(10) 0.0799(3) 0.56579(8) 0.0131(2) Uani 1 1 d . . . . .
C7 C 0.29083(10) 0.2995(3) 0.58487(8) 0.0144(2) Uani 1 1 d . . . . .
N8 N 0.33255(9) 0.4204(2) 0.52227(7) 0.0200(2) Uani 1 1 d . . . . .
O9 O 0.41048(8) 0.6143(2) 0.56750(6) 0.0235(2) Uani 1 1 d . . . . .
N10 N 0.41664(9) 0.6124(3) 0.66043(7) 0.0212(3) Uani 1 1 d . . . . .
C11 C 0.34354(10) 0.4213(3) 0.67140(8) 0.0165(3) Uani 1 1 d . . . . .
N12 N 0.31813(9) 0.3497(3) 0.75368(7) 0.0214(3) Uani 1 1 d . . . . .
N13 N 0.37608(9) 0.4919(3) 0.81969(7) 0.0211(3) Uani 1 1 d . . . . .
N14 N 0.42075(11) 0.6017(3) 0.88359(8) 0.0308(3) Uani 1 1 d . . . . .
N1S N 0.10918(9) 0.5172(2) 0.31065(7) 0.0165(2) Uani 1 1 d . . . . .
H1S H 0.1355(14) 0.367(4) 0.3426(11) 0.020 Uiso 1 1 d . U . . .
H2S H 0.1229(13) 0.508(4) 0.2530(11) 0.020 Uiso 1 1 d . U . . .
H3S H 0.1434(14) 0.674(4) 0.3388(11) 0.020 Uiso 1 1 d . U . . .
O2S O -0.01077(8) 0.5399(2) 0.29754(6) 0.0214(2) Uani 1 1 d . . . . .
H4S H -0.0237(15) 0.467(4) 0.3512(13) 0.032 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.3108(12) . ?
N2 N3 1.3411(15) . ?
N2 C6 1.3500(15) . ?
N3 N4 1.3135(14) . ?
N4 N5 1.3419(15) . ?
N5 C6 1.3327(15) . ?
C6 C7 1.4482(17) . ?
C7 N8 1.3076(16) . ?
C7 C11 1.4340(16) . ?
N8 O9 1.3766(14) . ?
O9 N10 1.3905(14) . ?
N10 C11 1.3048(18) . ?
C11 N12 1.3942(16) . ?
N12 N13 1.2689(15) . ?
N13 N14 1.1175(16) . ?
N1S O2S 1.4261(14) . ?
N1S H1S 0.877(18) . ?
N1S H2S 0.927(17) . ?
N1S H3S 0.904(18) . ?
O2S H4S 0.929(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N2 N3 121.55(10) . . ?
O1 N2 C6 129.71(11) . . ?
N3 N2 C6 108.72(10) . . ?
N4 N3 N2 105.71(10) . . ?
N3 N4 N5 111.72(10) . . ?
C6 N5 N4 105.59(10) . . ?
N5 C6 N2 108.25(11) . . ?
N5 C6 C7 125.96(11) . . ?
N2 C6 C7 125.76(11) . . ?
N8 C7 C11 108.69(11) . . ?
N8 C7 C6 123.53(11) . . ?
C11 C7 C6 127.78(11) . . ?
C7 N8 O9 105.67(10) . . ?
N8 O9 N10 111.31(9) . . ?
C11 N10 O9 105.01(10) . . ?
N10 C11 N12 125.75(12) . . ?
N10 C11 C7 109.32(11) . . ?
N12 C11 C7 124.92(12) . . ?
N13 N12 C11 112.02(11) . . ?
N14 N13 N12 172.36(14) . . ?
O2S N1S H1S 111.3(11) . . ?
O2S N1S H2S 106.2(10) . . ?
H1S N1S H2S 111.0(14) . . ?
O2S N1S H3S 110.1(10) . . ?
H1S N1S H3S 109.9(14) . . ?
H2S N1S H3S 108.3(14) . . ?
N1S O2S H4S 103.3(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
O1 N2 N3 N4 179.23(10) . . . . ?
C6 N2 N3 N4 0.34(13) . . . . ?
N2 N3 N4 N5 0.03(13) . . . . ?
N3 N4 N5 C6 -0.38(13) . . . . ?
N4 N5 C6 N2 0.58(13) . . . . ?
N4 N5 C6 C7 -177.37(11) . . . . ?
O1 N2 C6 N5 -179.36(11) . . . . ?
N3 N2 C6 N5 -0.58(13) . . . . ?
O1 N2 C6 C7 -1.4(2) . . . . ?
N3 N2 C6 C7 177.37(11) . . . . ?
N5 C6 C7 N8 -179.21(12) . . . . ?
N2 C6 C7 N8 3.2(2) . . . . ?
N5 C6 C7 C11 0.7(2) . . . . ?
N2 C6 C7 C11 -176.95(12) . . . . ?
C11 C7 N8 O9 0.25(14) . . . . ?
C6 C7 N8 O9 -179.87(11) . . . . ?
C7 N8 O9 N10 -0.08(14) . . . . ?
N8 O9 N10 C11 -0.14(14) . . . . ?
O9 N10 C11 N12 -178.37(12) . . . . ?
O9 N10 C11 C7 0.29(14) . . . . ?
N8 C7 C11 N10 -0.35(15) . . . . ?
C6 C7 C11 N10 179.77(12) . . . . ?
N8 C7 C11 N12 178.32(12) . . . . ?
C6 C7 C11 N12 -1.6(2) . . . . ?
N10 C11 N12 N13 -0.68(19) . . . . ?
C7 C11 N12 N13 -179.14(12) . . . . ?

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
N1S H1S O1 0.877(18) 1.910(19) 2.7846(15) 174.8(16) .
N1S H2S N5 0.927(17) 2.069(17) 2.9904(14) 172.0(15) 4_565
N1S H3S O1 0.904(18) 1.912(19) 2.7995(14) 166.8(15) 1_565
N1S H3S N2 0.904(18) 2.547(17) 3.3014(15) 141.2(13) 1_565
N1S H3S N3 0.904(18) 2.610(16) 3.0548(15) 111.1(12) 1_565
O2S H4S N4 0.929(19) 1.793(19) 2.6703(14) 156.3(17) 3_556

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053

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

data_shrv368
_database_code_depnum_ccdc_archive 'CCDC 1915168'
loop_
_audit_author_name
_audit_author_address
'Lauren A. Mitchell'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 N9 O2, H5 N2'
_chemical_formula_sum            'C3 H5 N11 O2'
_chemical_formula_weight         227.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.8837(9)
_cell_length_b                   4.8567(3)
_cell_length_c                   14.9766(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.973(2)
_cell_angle_gamma                90
_cell_volume                     909.39(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2933
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9021
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.803
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2112
_reflns_number_gt                1673
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0382P)²+0.1953P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2112
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.29419(7) 1.00579(18) 1.08876(5) 0.0217(2) Uani 1 1 d . . . . .
N2 N 0.31839(8) 1.0438(2) 1.00909(7) 0.0181(2) Uani 1 1 d . . . . .
N3 N 0.38894(8) 1.2360(2) 0.99749(7) 0.0233(2) Uani 1 1 d . . . . .
N4 N 0.39151(9) 1.2248(2) 0.91033(7) 0.0261(3) Uani 1 1 d . . . . .
N5 N 0.32423(8) 1.0292(2) 0.86575(7) 0.0239(2) Uani 1 1 d . . . . .
C6 C 0.27858(9) 0.9173(3) 0.92833(8) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.19896(9) 0.7015(3) 0.91196(8) 0.0194(3) Uani 1 1 d . . . . .
N8 N 0.16270(9) 0.5863(2) 0.97721(7) 0.0249(3) Uani 1 1 d . . . . .
O9 O 0.08973(7) 0.3920(2) 0.93431(6) 0.0293(2) Uani 1 1 d . . . . .
N10 N 0.08106(9) 0.3886(2) 0.84013(7) 0.0265(3) Uani 1 1 d . . . . .
C11 C 0.14765(9) 0.5761(3) 0.82625(8) 0.0211(3) Uani 1 1 d . . . . .
N12 N 0.16737(8) 0.6433(2) 0.74127(7) 0.0260(3) Uani 1 1 d . . . . .
N13 N 0.11059(8) 0.5037(2) 0.67598(7) 0.0261(3) Uani 1 1 d . . . . .
N14 N 0.06621(10) 0.3961(3) 0.61246(8) 0.0366(3) Uani 1 1 d . . . . .
N1S N 0.34282(8) 1.9952(2) 0.67729(7) 0.0185(2) Uani 1 1 d . . . . .
H1S H 0.3143(11) 1.844(3) 0.6430(10) 0.022 Uiso 1 1 d . U . . .
H2S H 0.3170(11) 2.156(3) 0.6481(9) 0.022 Uiso 1 1 d . U . . .
H3S H 0.3260(11) 1.990(3) 0.7315(11) 0.022 Uiso 1 1 d . U . . .
N2S N 0.45846(8) 2.0013(2) 0.69519(8) 0.0231(2) Uani 1 1 d . . . . .
H4S H 0.4734(12) 1.998(3) 0.6418(11) 0.028 Uiso 1 1 d . U . . .
H5S H 0.4829(11) 1.848(3) 0.7243(10) 0.028 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.3171(12) . ?
N2 C6 1.3431(15) . ?
N2 N3 1.3431(14) . ?
N3 N4 1.3150(14) . ?
N4 N5 1.3492(15) . ?
N5 C6 1.3364(16) . ?
C6 C7 1.4454(17) . ?
C7 N8 1.3065(16) . ?
C7 C11 1.4304(16) . ?
N8 O9 1.3768(14) . ?
O9 N10 1.3878(14) . ?
N10 C11 1.3021(17) . ?
C11 N12 1.3954(16) . ?
N12 N13 1.2673(14) . ?
N13 N14 1.1146(15) . ?
N1S N2S 1.4490(15) . ?
N1S H1S 0.922(15) . ?
N1S H2S 0.917(15) . ?
N1S H3S 0.889(16) . ?
N2S H4S 0.867(17) . ?
N2S H5S 0.882(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
O1 N2 C6 128.99(10) . . ?
O1 N2 N3 122.03(9) . . ?
C6 N2 N3 108.95(9) . . ?
N4 N3 N2 106.24(9) . . ?
N3 N4 N5 110.69(10) . . ?
C6 N5 N4 106.15(10) . . ?
N5 C6 N2 107.97(11) . . ?
N5 C6 C7 126.18(11) . . ?
N2 C6 C7 125.84(11) . . ?
N8 C7 C11 108.52(11) . . ?
N8 C7 C6 123.44(11) . . ?
C11 C7 C6 128.04(11) . . ?
C7 N8 O9 105.77(10) . . ?
N8 O9 N10 111.15(9) . . ?
C11 N10 O9 105.04(10) . . ?
N10 C11 N12 125.55(11) . . ?
N10 C11 C7 109.52(11) . . ?
N12 C11 C7 124.93(11) . . ?
N13 N12 C11 112.35(11) . . ?
N14 N13 N12 172.35(14) . . ?
N2S N1S H1S 111.9(9) . . ?
N2S N1S H2S 108.0(9) . . ?
H1S N1S H2S 111.4(12) . . ?
N2S N1S H3S 107.3(9) . . ?
H1S N1S H3S 109.5(13) . . ?
H2S N1S H3S 108.6(12) . . ?
N1S N2S H4S 106.0(10) . . ?
N1S N2S H5S 107.6(10) . . ?
H4S N2S H5S 107.9(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 N3 N4 -177.98(10) . . . . ?
C6 N2 N3 N4 -0.04(13) . . . . ?
N2 N3 N4 N5 -0.10(14) . . . . ?
N3 N4 N5 C6 0.20(14) . . . . ?
N4 N5 C6 N2 -0.22(13) . . . . ?
N4 N5 C6 C7 178.79(12) . . . . ?
O1 N2 C6 N5 177.92(11) . . . . ?
N3 N2 C6 N5 0.17(13) . . . . ?
O1 N2 C6 C7 -1.1(2) . . . . ?
N3 N2 C6 C7 -178.85(11) . . . . ?
N5 C6 C7 N8 174.90(12) . . . . ?
N2 C6 C7 N8 -6.3(2) . . . . ?
N5 C6 C7 C11 -4.4(2) . . . . ?
N2 C6 C7 C11 174.39(12) . . . . ?
C11 C7 N8 O9 -0.11(14) . . . . ?
C6 C7 N8 O9 -179.57(11) . . . . ?
C7 N8 O9 N10 -0.06(14) . . . . ?
N8 O9 N10 C11 0.21(13) . . . . ?
O9 N10 C11 N12 178.99(11) . . . . ?
O9 N10 C11 C7 -0.27(14) . . . . ?
N8 C7 C11 N10 0.25(15) . . . . ?
C6 C7 C11 N10 179.68(12) . . . . ?
N8 C7 C11 N12 -179.01(12) . . . . ?
C6 C7 C11 N12 0.4(2) . . . . ?
N10 C11 N12 N13 1.48(19) . . . . ?
C7 C11 N12 N13 -179.37(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1S H1S O1 0.922(15) 1.872(16) 2.7695(14) 163.9(12) 4_585
N1S H2S O1 0.917(15) 1.857(16) 2.7608(14) 168.1(13) 4_595
N1S H2S N2 0.917(15) 2.545(15) 3.3276(15) 143.6(11) 4_595
N1S H3S N5 0.889(16) 2.025(16) 2.8944(15) 165.2(13) 1_565
N2S H4S N3 0.867(17) 2.528(16) 3.1490(15) 129.2(12) 4_595
N2S H4S N4 0.867(17) 2.460(16) 3.0841(15) 129.5(12) 2_656
N2S H5S N2S 0.882(16) 2.102(16) 2.9814(13) 174.9(13) 2_646

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042

