# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shrv613
_database_code_depnum_ccdc_archive 'CCDC 1861409'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2018-08-10 deposited with the CCDC.	2019-09-11 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         'C4 H5 N9 O2, O H2'
_chemical_formula_sum            'C4 H7 N9 O3'
_chemical_formula_weight         229.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.1165(4)
_cell_length_b                   14.3444(6)
_cell_length_c                   7.2327(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.033(2)
_cell_angle_gamma                90
_cell_volume                     899.36(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1805
_cell_measurement_theta_min      3.285
_cell_measurement_theta_max      25.305

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            10599
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2541
_reflns_number_gt                1666
_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)'
_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)+(0.0510P)²+0.2321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2541
_refine_ls_number_parameters     151
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_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 0.35498(19) 0.35328(9) 0.5762(2) 0.0437(4) Uani 1 1 d . . . . .
H1A H 0.4415 0.3615 0.6658 0.052 Uiso 1 1 calc R U . . .
H1B H 0.3265 0.2981 0.5337 0.052 Uiso 1 1 calc R U . . .
C2 C 0.2657(2) 0.42565(10) 0.5037(2) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.1230(2) 0.43270(10) 0.3591(2) 0.0305(4) Uani 1 1 d . . . . .
N4 N 0.0387(2) 0.35885(10) 0.2580(2) 0.0415(4) Uani 1 1 d . . . . .
O5 O 0.0944(2) 0.27946(9) 0.2911(2) 0.0660(5) Uani 1 1 d . . . . .
O6 O -0.08914(17) 0.37456(10) 0.1381(2) 0.0547(4) Uani 1 1 d . . . . .
C7 C 0.08375(18) 0.52969(11) 0.3395(2) 0.0295(3) Uani 1 1 d . . . . .
N8 N -0.04270(18) 0.56881(11) 0.2184(2) 0.0429(4) Uani 1 1 d . . . . .
H8A H -0.0551 0.6282 0.2193 0.051 Uiso 1 1 calc R U . . .
H8B H -0.1117 0.5346 0.1396 0.051 Uiso 1 1 calc R U . . .
N9 N 0.19161(15) 0.58047(9) 0.46223(19) 0.0304(3) Uani 1 1 d . . . . .
N10 N 0.30231(15) 0.51456(9) 0.56290(19) 0.0306(3) Uani 1 1 d . . . . .
C11 C 0.42965(18) 0.54617(10) 0.7060(2) 0.0280(3) Uani 1 1 d . . . . .
N12 N 0.55323(16) 0.49622(10) 0.7927(2) 0.0380(4) Uani 1 1 d . . . . .
N13 N 0.64751(18) 0.55658(11) 0.9193(2) 0.0433(4) Uani 1 1 d . . . . .
N14 N 0.58593(18) 0.63834(10) 0.9088(2) 0.0423(4) Uani 1 1 d . . . . .
N15 N 0.44592(16) 0.63243(9) 0.7738(2) 0.0355(3) Uani 1 1 d . . . . .
H15 H 0.3794 0.6766 0.7384 0.043 Uiso 1 1 calc R U . . .
O16 O 0.29254(18) 0.79134(9) 0.7043(2) 0.0528(4) Uani 1 1 d D . . . .
H16B H 0.233(2) 0.8027(17) 0.5972(18) 0.079 Uiso 1 1 d D U . . .
H16A H 0.265(3) 0.8191(17) 0.786(3) 0.079 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
N1 C2 1.323(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C2 N10 1.3538(19) . ?
C2 C3 1.398(2) . ?
C3 N4 1.378(2) . ?
C3 C7 1.433(2) . ?
N4 O5 1.240(2) . ?
N4 O6 1.239(2) . ?
C7 N9 1.321(2) . ?
C7 N8 1.336(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 N10 1.4098(17) . ?
N10 C11 1.371(2) . ?
C11 N12 1.319(2) . ?
C11 N15 1.322(2) . ?
N12 N13 1.356(2) . ?
N13 N14 1.292(2) . ?
N14 N15 1.348(2) . ?
N15 H15 0.8600 . ?
O16 H16B 0.814(9) . ?
O16 H16A 0.814(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
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C2 N10 123.54(16) . . ?
N1 C2 C3 131.99(15) . . ?
N10 C2 C3 104.47(13) . . ?
N4 C3 C2 125.33(15) . . ?
N4 C3 C7 127.81(16) . . ?
C2 C3 C7 106.86(13) . . ?
O5 N4 O6 122.84(15) . . ?
O5 N4 C3 118.43(17) . . ?
O6 N4 C3 118.73(15) . . ?
N9 C7 N8 121.37(15) . . ?
N9 C7 C3 110.98(14) . . ?
N8 C7 C3 127.65(15) . . ?
C7 N8 H8A 120.0 . . ?
C7 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C7 N9 N10 104.01(12) . . ?
C2 N10 C11 128.20(14) . . ?
C2 N10 N9 113.66(13) . . ?
C11 N10 N9 118.13(12) . . ?
N12 C11 N15 110.53(14) . . ?
N12 C11 N10 125.34(14) . . ?
N15 C11 N10 124.12(14) . . ?
C11 N12 N13 104.11(14) . . ?
N14 N13 N12 111.52(14) . . ?
N13 N14 N15 106.37(13) . . ?
C11 N15 N14 107.45(13) . . ?
C11 N15 H15 126.3 . . ?
N14 N15 H15 126.3 . . ?
H16B O16 H16A 109.0(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 C2 C3 N4 1.7(3) . . . . ?
N10 C2 C3 N4 -178.94(16) . . . . ?
N1 C2 C3 C7 -178.65(17) . . . . ?
N10 C2 C3 C7 0.73(18) . . . . ?
C2 C3 N4 O5 -2.7(3) . . . . ?
C7 C3 N4 O5 177.70(17) . . . . ?
C2 C3 N4 O6 177.34(16) . . . . ?
C7 C3 N4 O6 -2.3(3) . . . . ?
N4 C3 C7 N9 179.26(15) . . . . ?
C2 C3 C7 N9 -0.40(19) . . . . ?
N4 C3 C7 N8 -0.3(3) . . . . ?
C2 C3 C7 N8 -179.95(16) . . . . ?
N8 C7 N9 N10 179.48(15) . . . . ?
C3 C7 N9 N10 -0.11(17) . . . . ?
N1 C2 N10 C11 -2.2(3) . . . . ?
C3 C2 N10 C11 178.39(15) . . . . ?
N1 C2 N10 N9 178.59(15) . . . . ?
C3 C2 N10 N9 -0.86(18) . . . . ?
C7 N9 N10 C2 0.62(17) . . . . ?
C7 N9 N10 C11 -178.70(14) . . . . ?
C2 N10 C11 N12 11.4(3) . . . . ?
N9 N10 C11 N12 -169.36(15) . . . . ?
C2 N10 C11 N15 -169.77(16) . . . . ?
N9 N10 C11 N15 9.5(2) . . . . ?
N15 C11 N12 N13 0.14(18) . . . . ?
N10 C11 N12 N13 179.09(15) . . . . ?
C11 N12 N13 N14 -0.6(2) . . . . ?
N12 N13 N14 N15 0.8(2) . . . . ?
N12 C11 N15 N14 0.35(19) . . . . ?
N10 C11 N15 N14 -178.62(15) . . . . ?
N13 N14 N15 C11 -0.72(19) . . . . ?

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 N12 0.86 2.24 2.858(2) 128.3 .
N1 H1A O16 0.86 2.52 3.237(2) 141.1 2_646
N1 H1B O5 0.86 2.31 2.826(2) 118.9 .
N1 H1B N14 0.86 2.42 3.126(2) 139.8 2_646
N8 H8A O5 0.86 2.20 3.056(2) 177.5 2
N8 H8B O6 0.86 2.30 2.851(2) 121.6 .
N8 H8B N13 0.86 2.30 2.984(2) 136.5 1_454
N15 H15 O16 0.86 1.81 2.6399(18) 161.8 .
O16 H16B O6 0.814(9) 2.072(13) 2.8552(19) 161(2) 2
O16 H16A N9 0.814(9) 2.162(12) 2.9615(19) 167(3) 4_576

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.231
_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_shrv736
_database_code_depnum_ccdc_archive 'CCDC 1936195'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-09-11 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         'C4 H8 N7 O2, Cl, 2(H2 O)'
_chemical_formula_sum            'C4 H12 Cl N7 O4'
_chemical_formula_weight         257.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.5265(6)
_cell_length_b                   6.9696(5)
_cell_length_c                   18.0794(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.241(2)
_cell_angle_gamma                90
_cell_volume                     1068.02(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1938
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.95

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    0.374
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6917
_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            11746
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         30.073
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3034
_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)'
_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)+(0.0524P)²+0.1426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3034
_refine_ls_number_parameters     161
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.992
_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 0.37784(19) 0.7190(3) 0.60686(8) 0.0450(4) Uani 1 1 d . . . . .
O2 O 0.62128(19) 0.8182(3) 0.61644(8) 0.0505(5) Uani 1 1 d . . . . .
N3 N 0.4991(2) 0.7639(3) 0.57827(9) 0.0308(4) Uani 1 1 d . . . . .
C4 C 0.4984(2) 0.7550(3) 0.50174(10) 0.0238(4) Uani 1 1 d . . . . .
C5 C 0.3713(2) 0.6922(3) 0.45217(9) 0.0228(4) Uani 1 1 d . . . . .
N6 N 0.2327(2) 0.6251(2) 0.46564(9) 0.0304(4) Uani 1 1 d . . . . .
H6A H 0.1661 0.5870 0.4295 0.036 Uiso 1 1 calc R U . . .
H6B H 0.2088 0.6193 0.5106 0.036 Uiso 1 1 calc R U . . .
N7 N 0.42698(19) 0.7105(2) 0.38342(8) 0.0287(4) Uani 1 1 d . . . . .
C8 C 0.3573(3) 0.6586(3) 0.31365(10) 0.0294(4) Uani 1 1 d . . . . .
N9 N 0.2025(2) 0.6549(3) 0.30150(9) 0.0399(5) Uani 1 1 d . . . . .
H9A H 0.1573 0.6235 0.2584 0.048 Uiso 1 1 calc R U . . .
H9B H 0.1465 0.6840 0.3367 0.048 Uiso 1 1 calc R U . . .
N10 N 0.4500(2) 0.6167(3) 0.26358(9) 0.0432(5) Uani 1 1 d . . . . .
H10A H 0.4109 0.5843 0.2195 0.052 Uiso 1 1 calc R U . . .
H10B H 0.5507 0.6214 0.2745 0.052 Uiso 1 1 calc R U . . .
N11 N 0.5843(2) 0.7772(3) 0.38809(9) 0.0334(4) Uani 1 1 d . . . . .
C12 C 0.6251(2) 0.8042(3) 0.45966(10) 0.0268(4) Uani 1 1 d . . . . .
N13 N 0.7676(2) 0.8703(3) 0.48605(10) 0.0377(5) Uani 1 1 d . . . . .
H13A H 0.8361 0.8966 0.4559 0.045 Uiso 1 1 calc R U . . .
H13B H 0.7908 0.8865 0.5331 0.045 Uiso 1 1 calc R U . . .
Cl14 Cl 0.98609(7) 0.99492(8) 0.35188(3) 0.03741(16) Uani 1 1 d . . . . .
O15 O 0.9549(2) 0.4353(3) 0.40160(9) 0.0470(4) Uani 1 1 d D . . . .
H15A H 0.902(3) 0.484(3) 0.3655(10) 0.049(8) Uiso 1 1 d D . . . .
H15B H 0.965(4) 0.3232(19) 0.3873(15) 0.079(11) Uiso 1 1 d D . . . .
O16 O 0.7892(2) 0.6201(3) 0.27592(10) 0.0506(5) Uani 1 1 d D . . . .
H16A H 0.810(5) 0.728(3) 0.2921(19) 0.120(16) Uiso 1 1 d D . . . .
H16B H 0.831(4) 0.618(5) 0.2369(11) 0.095(12) Uiso 1 1 d 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 1.245(2) . ?
O2 N3 1.245(2) . ?
N3 C4 1.384(2) . ?
C4 C5 1.399(3) . ?
C4 C12 1.429(3) . ?
C5 N6 1.318(2) . ?
C5 N7 1.384(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 C8 1.383(2) . ?
N7 N11 1.414(2) . ?
C8 N10 1.298(3) . ?
C8 N9 1.314(3) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 C12 1.316(2) . ?
C12 N13 1.338(3) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
O15 H15A 0.824(9) . ?
O15 H15B 0.830(10) . ?
O16 H16A 0.822(10) . ?
O16 H16B 0.823(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 121.94(16) . . ?
O2 N3 C4 118.68(17) . . ?
O1 N3 C4 119.38(16) . . ?
N3 C4 C5 124.94(17) . . ?
N3 C4 C12 126.89(17) . . ?
C5 C4 C12 108.16(16) . . ?
N6 C5 N7 126.91(17) . . ?
N6 C5 C4 129.81(17) . . ?
N7 C5 C4 103.25(16) . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C8 N7 C5 129.78(17) . . ?
C8 N7 N11 116.84(16) . . ?
C5 N7 N11 113.11(15) . . ?
N10 C8 N9 123.77(18) . . ?
N10 C8 N7 117.43(19) . . ?
N9 C8 N7 118.80(18) . . ?
C8 N9 H9A 120.0 . . ?
C8 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C8 N10 H10A 120.0 . . ?
C8 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C12 N11 N7 104.69(15) . . ?
N11 C12 N13 122.19(18) . . ?
N11 C12 C4 110.76(17) . . ?
N13 C12 C4 127.05(17) . . ?
C12 N13 H13A 120.0 . . ?
C12 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
H15A O15 H15B 102.1(19) . . ?
H16A O16 H16B 103(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
O2 N3 C4 C5 178.26(19) . . . . ?
O1 N3 C4 C5 -2.3(3) . . . . ?
O2 N3 C4 C12 -0.7(3) . . . . ?
O1 N3 C4 C12 178.79(19) . . . . ?
N3 C4 C5 N6 -2.3(3) . . . . ?
C12 C4 C5 N6 176.85(19) . . . . ?
N3 C4 C5 N7 179.76(18) . . . . ?
C12 C4 C5 N7 -1.1(2) . . . . ?
N6 C5 N7 C8 -2.7(3) . . . . ?
C4 C5 N7 C8 175.38(19) . . . . ?
N6 C5 N7 N11 -176.53(18) . . . . ?
C4 C5 N7 N11 1.5(2) . . . . ?
C5 N7 C8 N10 -152.5(2) . . . . ?
N11 N7 C8 N10 21.1(3) . . . . ?
C5 N7 C8 N9 27.8(3) . . . . ?
N11 N7 C8 N9 -158.58(19) . . . . ?
C8 N7 N11 C12 -176.03(17) . . . . ?
C5 N7 N11 C12 -1.3(2) . . . . ?
N7 N11 C12 N13 -179.14(18) . . . . ?
N7 N11 C12 C4 0.5(2) . . . . ?
N3 C4 C12 N11 179.49(19) . . . . ?
C5 C4 C12 N11 0.4(2) . . . . ?
N3 C4 C12 N13 -0.9(3) . . . . ?
C5 C4 C12 N13 -180.0(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
N6 H6A N9 0.86 2.41 2.958(2) 121.7 .
N6 H6A O15 0.86 2.10 2.846(2) 144.6 1_455
N6 H6B O1 0.86 2.25 2.791(2) 121.4 .
N6 H6B O15 0.86 2.26 3.055(2) 154.2 3_666
N9 H9A Cl14 0.86 2.40 3.2482(17) 171.0 2_645
N9 H9B N6 0.86 2.40 2.958(2) 122.8 .
N9 H9B Cl14 0.86 2.59 3.196(2) 128.1 1_455
N10 H10A O1 0.86 2.45 3.056(2) 128.5 4_575
N10 H10B O16 0.86 2.03 2.876(3) 167.3 .
N13 H13A Cl14 0.86 2.48 3.3303(18) 168.3 .
N13 H13B O2 0.86 2.25 2.808(2) 122.7 .
N13 H13B Cl14 0.86 2.79 3.5412(18) 147.3 3_776
O15 H15A O16 0.824(9) 2.027(10) 2.850(3) 175(3) .
O15 H15B Cl14 0.830(10) 2.388(10) 3.217(2) 177(3) 1_545
O16 H16A Cl14 0.822(10) 2.55(2) 3.321(2) 156(4) .
O16 H16B Cl14 0.823(10) 2.510(17) 3.2762(18) 155(3) 2_745

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.058


# start Validation Reply Form
_vrf_PLAT416_shrv736             
;
PROBLEM: Short Intra D-H..H-D       H6A      ..H9B      .       1.80 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_shrv725
_database_code_depnum_ccdc_archive 'CCDC 1936194'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-09-11 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         'C5 H7 N8 O2, Cl, H2 O'
_chemical_formula_sum            'C5 H9 Cl N8 O3'
_chemical_formula_weight         264.65

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      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                   7.8649(6)
_cell_length_b                   7.8722(6)
_cell_length_c                   8.8770(6)
_cell_angle_alpha                87.756(2)
_cell_angle_beta                 74.218(2)
_cell_angle_gamma                73.265(2)
_cell_volume                     506.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1845
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      29.93

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.393
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6981
_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            6095
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.386
_diffrn_reflns_theta_max         30.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2773
_reflns_number_gt                2140
_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)'
_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)+(0.0499P)²+0.1799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2773
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.029
_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
O1 O 0.99126(18) 0.38747(17) 0.32342(16) 0.0344(3) Uani 1 1 d . . . . .
O2 O 0.89963(18) 0.31050(17) 0.56289(17) 0.0349(3) Uani 1 1 d . . . . .
N3 N 0.88001(19) 0.41143(18) 0.45501(17) 0.0239(3) Uani 1 1 d . . . . .
C4 C 0.7245(2) 0.5596(2) 0.48208(19) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.5765(2) 0.6152(2) 0.62302(19) 0.0231(3) Uani 1 1 d . . . . .
N6 N 0.5643(2) 0.5403(2) 0.76204(19) 0.0353(4) Uani 1 1 d . . . . .
H6A H 0.4679 0.5808 0.8390 0.042 Uiso 1 1 calc R U . . .
H6B H 0.6529 0.4518 0.7744 0.042 Uiso 1 1 calc R U . . .
N7 N 0.44294(19) 0.75256(19) 0.59816(16) 0.0250(3) Uani 1 1 d . . . . .
N8 N 0.50669(18) 0.78409(18) 0.44002(16) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.4070(2) 0.9059(2) 0.35754(19) 0.0215(3) Uani 1 1 d . . . . .
N10 N 0.24529(19) 1.00651(19) 0.43468(18) 0.0277(3) Uani 1 1 d . . . . .
H10A H 0.1798 1.0844 0.3866 0.033 Uiso 1 1 calc R U . . .
H10B H 0.2041 0.9950 0.5336 0.033 Uiso 1 1 calc R U . . .
N11 N 0.47900(19) 0.91658(18) 0.20471(17) 0.0254(3) Uani 1 1 d . . . . .
C12 C 0.6485(2) 0.8124(2) 0.1355(2) 0.0263(4) Uani 1 1 d . . . . .
N13 N 0.7240(2) 0.8237(2) -0.01386(19) 0.0419(4) Uani 1 1 d . . . . .
H13A H 0.6647 0.8984 -0.0683 0.050 Uiso 1 1 calc R U . . .
H13B H 0.8330 0.7564 -0.0576 0.050 Uiso 1 1 calc R U . . .
N14 N 0.74907(19) 0.69056(19) 0.21629(16) 0.0259(3) Uani 1 1 d . . . . .
H14 H 0.8587 0.6266 0.1699 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6741(2) 0.6724(2) 0.36896(19) 0.0212(3) Uani 1 1 d . . . . .
Cl16 Cl 0.15568(6) 0.67533(7) 0.01499(6) 0.03700(15) Uani 1 1 d . . . . .
O17 O 0.0396(2) 0.9816(2) 0.75095(17) 0.0427(4) Uani 1 1 d D . . . .
H17A H -0.013(3) 1.070(2) 0.810(3) 0.064 Uiso 1 1 d D U . . .
H17B H 0.100(3) 0.911(3) 0.800(3) 0.064 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 N3 1.2377(19) . ?
O2 N3 1.2339(18) . ?
N3 C4 1.398(2) . ?
C4 C15 1.378(2) . ?
C4 C5 1.438(2) . ?
C5 N7 1.332(2) . ?
C5 N6 1.338(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 N8 1.3947(19) . ?
N8 C15 1.352(2) . ?
N8 C9 1.376(2) . ?
C9 N10 1.305(2) . ?
C9 N11 1.330(2) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 C12 1.338(2) . ?
C12 N13 1.308(2) . ?
C12 N14 1.370(2) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
N14 C15 1.343(2) . ?
N14 H14 0.8600 . ?
O17 H17A 0.822(10) . ?
O17 H17B 0.817(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 123.11(14) . . ?
O2 N3 C4 118.61(14) . . ?
O1 N3 C4 118.28(14) . . ?
C15 C4 N3 124.98(15) . . ?
C15 C4 C5 105.95(14) . . ?
N3 C4 C5 128.74(15) . . ?
N7 C5 N6 122.20(16) . . ?
N7 C5 C4 110.99(14) . . ?
N6 C5 C4 126.77(15) . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C5 N7 N8 103.76(13) . . ?
C15 N8 C9 121.67(14) . . ?
C15 N8 N7 113.36(13) . . ?
C9 N8 N7 124.78(13) . . ?
N10 C9 N11 123.16(15) . . ?
N10 C9 N8 117.72(15) . . ?
N11 C9 N8 119.12(14) . . ?
C9 N10 H10A 120.0 . . ?
C9 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C9 N11 C12 119.36(14) . . ?
N13 C12 N11 120.46(15) . . ?
N13 C12 N14 117.47(15) . . ?
N11 C12 N14 122.06(15) . . ?
C12 N13 H13A 120.0 . . ?
C12 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C15 N14 C12 119.07(14) . . ?
C15 N14 H14 120.5 . . ?
C12 N14 H14 120.5 . . ?
N14 C15 N8 118.52(14) . . ?
N14 C15 C4 135.54(15) . . ?
N8 C15 C4 105.92(14) . . ?
H17A O17 H17B 105(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
O2 N3 C4 C15 -172.53(16) . . . . ?
O1 N3 C4 C15 7.2(2) . . . . ?
O2 N3 C4 C5 -0.1(3) . . . . ?
O1 N3 C4 C5 179.63(16) . . . . ?
C15 C4 C5 N7 0.39(19) . . . . ?
N3 C4 C5 N7 -173.15(16) . . . . ?
C15 C4 C5 N6 178.21(17) . . . . ?
N3 C4 C5 N6 4.7(3) . . . . ?
N6 C5 N7 N8 -177.83(16) . . . . ?
C4 C5 N7 N8 0.10(18) . . . . ?
C5 N7 N8 C15 -0.60(18) . . . . ?
C5 N7 N8 C9 174.44(15) . . . . ?
C15 N8 C9 N10 178.83(15) . . . . ?
N7 N8 C9 N10 4.2(2) . . . . ?
C15 N8 C9 N11 -1.5(2) . . . . ?
N7 N8 C9 N11 -176.16(14) . . . . ?
N10 C9 N11 C12 177.79(16) . . . . ?
N8 C9 N11 C12 -1.8(2) . . . . ?
C9 N11 C12 N13 -178.29(17) . . . . ?
C9 N11 C12 N14 1.9(3) . . . . ?
N13 C12 N14 C15 -178.41(17) . . . . ?
N11 C12 N14 C15 1.4(3) . . . . ?
C12 N14 C15 N8 -4.6(2) . . . . ?
C12 N14 C15 C4 174.20(18) . . . . ?
C9 N8 C15 N14 4.8(2) . . . . ?
N7 N8 C15 N14 179.98(14) . . . . ?
C9 N8 C15 C4 -174.36(15) . . . . ?
N7 N8 C15 C4 0.85(18) . . . . ?
N3 C4 C15 N14 -5.8(3) . . . . ?
C5 C4 C15 N14 -179.62(18) . . . . ?
N3 C4 C15 N8 173.13(15) . . . . ?
C5 C4 C15 N8 -0.72(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
N6 H6A Cl16 0.86 2.44 3.2856(17) 166.0 1_556
N6 H6B O2 0.86 2.34 2.884(2) 121.7 .
N6 H6B Cl16 0.86 2.70 3.4065(16) 140.6 2_666
N10 H10A O1 0.86 2.55 3.3692(19) 158.8 1_465
N10 H10A O2 0.86 2.56 3.0325(19) 115.5 1_465
N10 H10A O17 0.86 2.54 3.102(2) 123.8 2_576
N10 H10B O17 0.86 2.03 2.865(2) 164.0 .
N13 H13A N11 0.86 2.13 2.987(2) 179.3 2_675
N13 H13B O1 0.86 2.51 3.193(2) 137.1 2_765
N13 H13B Cl16 0.86 2.68 3.3350(18) 133.8 1_655
N14 H14 O1 0.86 2.44 2.9011(19) 114.6 .
N14 H14 Cl16 0.86 2.49 3.1815(15) 137.5 1_655
N14 H14 Cl16 0.86 2.99 3.3848(16) 110.5 2_665
O17 H17A Cl16 0.822(10) 2.386(10) 3.2072(15) 178(3) 2_576
O17 H17B Cl16 0.817(10) 2.642(15) 3.4047(15) 156(3) 1_556

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055

