# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_shrv657
_database_code_depnum_ccdc_archive 'CCDC 1906614'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-07-04 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 H2 N8 O3'
_chemical_formula_sum            'C3 H2 N8 O3'
_chemical_formula_weight         198.13

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                   6.6953(9)
_cell_length_b                   6.8192(9)
_cell_length_c                   15.5018(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     707.76(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2487
_cell_measurement_theta_min      2.628
_cell_measurement_theta_max      24.989

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_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            8427
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_max         30.011
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2020
_reflns_number_gt                1586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_max     0.957
_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)'
_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)+(0.0366P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2020
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.032
_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
O1 O 0.9826(3) 0.2908(2) 0.20205(10) 0.0434(4) Uani 1 1 d . . . . .
O2 O 0.8145(3) 0.0970(2) 0.11811(9) 0.0443(4) Uani 1 1 d . . . . .
N3 N 0.8474(3) 0.1748(3) 0.18812(11) 0.0319(4) Uani 1 1 d . . . . .
C4 C 0.7155(3) 0.1276(3) 0.25747(13) 0.0271(4) Uani 1 1 d . . . . .
N5 N 0.5981(3) -0.0251(3) 0.25753(12) 0.0363(4) Uani 1 1 d . . . . .
N6 N 0.4864(3) -0.0187(3) 0.33147(13) 0.0391(5) Uani 1 1 d . . . . .
C7 C 0.5426(3) 0.1431(3) 0.37260(13) 0.0288(4) Uani 1 1 d . . . . .
N8 N 0.4642(3) 0.2129(3) 0.44702(11) 0.0343(4) Uani 1 1 d . . . . .
N9 N 0.5347(3) 0.3815(2) 0.47077(10) 0.0299(4) Uani 1 1 d . . . . .
O10 O 0.4721(3) 0.4625(2) 0.53776(9) 0.0438(4) Uani 1 1 d . . . . .
C11 C 0.6869(3) 0.4854(3) 0.42137(11) 0.0252(4) Uani 1 1 d . . . . .
N12 N 0.7341(3) 0.6583(2) 0.45315(11) 0.0353(5) Uani 1 1 d . . . . .
H12A H 0.8244 0.7312 0.4272 0.042 Uiso 1 1 calc R U . . .
H12B H 0.6754 0.7009 0.5003 0.042 Uiso 1 1 calc R U . . .
N13 N 0.7678(3) 0.4144(2) 0.35224(10) 0.0261(4) Uani 1 1 d . . . . .
N14 N 0.6894(2) 0.2378(2) 0.32925(9) 0.0232(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.221(2) . ?
O2 N3 1.228(2) . ?
N3 C4 1.428(3) . ?
C4 N5 1.305(3) . ?
C4 N14 1.354(3) . ?
N5 N6 1.369(3) . ?
N6 C7 1.328(3) . ?
C7 N8 1.354(3) . ?
C7 N14 1.354(3) . ?
N8 N9 1.296(2) . ?
N9 O10 1.249(2) . ?
N9 C11 1.459(3) . ?
C11 N13 1.294(3) . ?
C11 N12 1.316(3) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N13 N14 1.362(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 N3 O2 124.72(19) . . ?
O1 N3 C4 118.12(16) . . ?
O2 N3 C4 117.15(18) . . ?
N5 C4 N14 111.37(18) . . ?
N5 C4 N3 123.60(19) . . ?
N14 C4 N3 124.98(17) . . ?
C4 N5 N6 107.71(17) . . ?
C7 N6 N5 105.89(17) . . ?
N6 C7 N8 126.24(19) . . ?
N6 C7 N14 111.30(18) . . ?
N8 C7 N14 122.44(17) . . ?
N9 N8 C7 114.38(17) . . ?
O10 N9 N8 120.43(18) . . ?
O10 N9 C11 117.16(17) . . ?
N8 N9 C11 122.41(17) . . ?
N13 C11 N12 123.0(2) . . ?
N13 C11 N9 123.07(18) . . ?
N12 C11 N9 113.96(18) . . ?
C11 N12 H12A 120.0 . . ?
C11 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C11 N13 N14 112.70(17) . . ?
C4 N14 C7 103.70(16) . . ?
C4 N14 N13 131.01(16) . . ?
C7 N14 N13 124.88(16) . . ?

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 N3 C4 N5 -163.0(2) . . . . ?
O2 N3 C4 N5 17.9(3) . . . . ?
O1 N3 C4 N14 20.0(3) . . . . ?
O2 N3 C4 N14 -159.13(18) . . . . ?
N14 C4 N5 N6 0.5(2) . . . . ?
N3 C4 N5 N6 -176.87(19) . . . . ?
C4 N5 N6 C7 0.7(2) . . . . ?
N5 N6 C7 N8 176.7(2) . . . . ?
N5 N6 C7 N14 -1.6(2) . . . . ?
N6 C7 N8 N9 -175.1(2) . . . . ?
N14 C7 N8 N9 3.1(3) . . . . ?
C7 N8 N9 O10 179.03(18) . . . . ?
C7 N8 N9 C11 -0.5(3) . . . . ?
O10 N9 C11 N13 177.95(19) . . . . ?
N8 N9 C11 N13 -2.5(3) . . . . ?
O10 N9 C11 N12 -2.4(3) . . . . ?
N8 N9 C11 N12 177.15(19) . . . . ?
N12 C11 N13 N14 -177.09(18) . . . . ?
N9 C11 N13 N14 2.6(3) . . . . ?
N5 C4 N14 C7 -1.5(2) . . . . ?
N3 C4 N14 C7 175.89(19) . . . . ?
N5 C4 N14 N13 -174.24(18) . . . . ?
N3 C4 N14 N13 3.1(3) . . . . ?
N6 C7 N14 C4 1.9(2) . . . . ?
N8 C7 N14 C4 -176.48(19) . . . . ?
N6 C7 N14 N13 175.27(16) . . . . ?
N8 C7 N14 N13 -3.1(3) . . . . ?
C11 N13 N14 C4 171.5(2) . . . . ?
C11 N13 N14 C7 0.1(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
N12 H12A O1 0.88 2.42 3.194(2) 147.2 3_755
N12 H12A O10 0.88 2.37 3.041(2) 132.7 4_566
N12 H12B O2 0.88 2.29 3.071(2) 148.1 2_665

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.041



# start Validation Reply Form
_vrf_PLAT430_shrv657             
;
PROBLEM: Short Inter D...A Contact  N5       ..N14              2.85 Ang.  
RESPONSE: High-density energetic materials often display close contacts.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv701
_database_code_depnum_ccdc_archive 'CCDC 1906615'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_shrv701             
;
PROBLEM: Short Inter D...A Contact  O16      ..N7       .       2.86 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
# Added during the CSD deposition process: Friday 29 March 2019 01:55 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 H5 N8 O, N O3'
_chemical_formula_sum            'C3 H5 N9 O4'
_chemical_formula_weight         231.16

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

_cell_length_a                   5.4287(3)
_cell_length_b                   9.3438(5)
_cell_length_c                   16.7314(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     848.70(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2614
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.16

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.557
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6976
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            10093
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         30.036
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2408
_reflns_number_gt                1768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_max     0.952
_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)'
_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)+(0.0378P)²+0.0506P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2408
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0387(4) 0.5923(2) 0.30144(11) 0.0409(5) Uani 1 1 d . . . . .
H1A H 0.0460 0.5056 0.2843 0.049 Uiso 1 1 calc R U . . .
H1B H -0.0830 0.6461 0.2881 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2132(4) 0.6424(2) 0.34790(13) 0.0290(4) Uani 1 1 d . . . . .
N3 N 0.4145(3) 0.57742(19) 0.37515(11) 0.0355(4) Uani 1 1 d . . . . .
H3 H 0.4521 0.4905 0.3634 0.043 Uiso 1 1 calc R U . . .
N4 N 0.5566(3) 0.66244(19) 0.42384(11) 0.0359(4) Uani 1 1 d . . . . .
C5 C 0.4345(4) 0.7817(2) 0.42532(12) 0.0283(4) Uani 1 1 d . . . . .
N6 N 0.5004(3) 0.90101(19) 0.46700(11) 0.0332(4) Uani 1 1 d . . . . .
N7 N 0.3433(3) 1.00361(19) 0.46203(11) 0.0323(4) Uani 1 1 d . . . . .
O8 O 0.3792(4) 1.11734(19) 0.49846(11) 0.0524(5) Uani 1 1 d . . . . .
C9 C 0.1142(4) 0.9954(2) 0.41324(13) 0.0292(5) Uani 1 1 d . . . . .
N10 N -0.0189(4) 1.1124(2) 0.41700(13) 0.0444(5) Uani 1 1 d . . . . .
H10A H -0.1552 1.1180 0.3910 0.053 Uiso 1 1 calc R U . . .
H10B H 0.0301 1.1835 0.4455 0.053 Uiso 1 1 calc R U . . .
N11 N 0.0555(3) 0.88383(19) 0.37217(10) 0.0306(4) Uani 1 1 d . . . . .
N12 N 0.2246(3) 0.77553(17) 0.38015(10) 0.0263(4) Uani 1 1 d . . . . .
N13 N 0.4618(4) 0.2377(2) 0.30947(11) 0.0368(4) Uani 1 1 d . . . . .
O14 O 0.2947(4) 0.2962(2) 0.27192(14) 0.0653(6) Uani 1 1 d . . . . .
O15 O 0.6072(4) 0.3133(2) 0.34806(15) 0.0792(7) Uani 1 1 d . . . . .
O16 O 0.4899(3) 0.10647(18) 0.30824(10) 0.0486(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.312(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C2 N3 1.331(3) . ?
C2 N12 1.357(3) . ?
N3 N4 1.375(3) . ?
N3 H3 0.8600 . ?
N4 C5 1.296(3) . ?
C5 N6 1.363(3) . ?
C5 N12 1.368(3) . ?
N6 N7 1.286(2) . ?
N7 O8 1.241(2) . ?
N7 C9 1.490(3) . ?
C9 N11 1.289(3) . ?
C9 N10 1.312(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 N12 1.373(2) . ?
N13 O14 1.232(3) . ?
N13 O16 1.236(2) . ?
N13 O15 1.240(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C2 N3 129.3(2) . . ?
N1 C2 N12 126.56(19) . . ?
N3 C2 N12 104.14(18) . . ?
C2 N3 N4 113.60(17) . . ?
C2 N3 H3 123.2 . . ?
N4 N3 H3 123.2 . . ?
C5 N4 N3 102.77(16) . . ?
N4 C5 N6 125.36(18) . . ?
N4 C5 N12 112.28(18) . . ?
N6 C5 N12 122.36(18) . . ?
N7 N6 C5 113.77(17) . . ?
O8 N7 N6 120.18(19) . . ?
O8 N7 C9 116.39(18) . . ?
N6 N7 C9 123.43(17) . . ?
N11 C9 N10 124.3(2) . . ?
N11 C9 N7 122.69(17) . . ?
N10 C9 N7 113.01(19) . . ?
C9 N10 H10A 120.0 . . ?
C9 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C9 N11 N12 112.28(16) . . ?
C2 N12 C5 107.22(16) . . ?
C2 N12 N11 127.32(17) . . ?
C5 N12 N11 125.43(16) . . ?
O14 N13 O16 121.5(2) . . ?
O14 N13 O15 118.8(2) . . ?
O16 N13 O15 119.6(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
N1 C2 N3 N4 -179.2(2) . . . . ?
N12 C2 N3 N4 0.1(2) . . . . ?
C2 N3 N4 C5 0.0(2) . . . . ?
N3 N4 C5 N6 179.24(19) . . . . ?
N3 N4 C5 N12 -0.1(2) . . . . ?
N4 C5 N6 N7 -176.86(19) . . . . ?
N12 C5 N6 N7 2.4(3) . . . . ?
C5 N6 N7 O8 178.67(19) . . . . ?
C5 N6 N7 C9 -1.9(3) . . . . ?
O8 N7 C9 N11 179.6(2) . . . . ?
N6 N7 C9 N11 0.2(3) . . . . ?
O8 N7 C9 N10 -0.6(3) . . . . ?
N6 N7 C9 N10 179.95(19) . . . . ?
N10 C9 N11 N12 -178.68(19) . . . . ?
N7 C9 N11 N12 1.1(3) . . . . ?
N1 C2 N12 C5 179.1(2) . . . . ?
N3 C2 N12 C5 -0.1(2) . . . . ?
N1 C2 N12 N11 1.2(4) . . . . ?
N3 C2 N12 N11 -178.00(18) . . . . ?
N4 C5 N12 C2 0.1(2) . . . . ?
N6 C5 N12 C2 -179.22(19) . . . . ?
N4 C5 N12 N11 178.08(18) . . . . ?
N6 C5 N12 N11 -1.3(3) . . . . ?
C9 N11 N12 C2 177.0(2) . . . . ?
C9 N11 N12 C5 -0.6(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
N1 H1A O14 0.86 2.39 3.135(3) 145.8 .
N1 H1B O14 0.86 2.07 2.901(3) 161.4 3
N3 H3 N13 0.86 2.53 3.369(3) 165.5 .
N3 H3 O14 0.86 2.52 3.211(3) 137.5 .
N3 H3 O15 0.86 1.88 2.719(3) 166.3 .
N10 H10A O15 0.86 2.35 2.995(3) 132.4 1_465
N10 H10A O16 0.86 2.37 3.228(3) 172.0 1_465
N10 H10B O8 0.86 2.24 2.946(3) 139.6 4_476

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.040



