# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_compd10
_database_code_depnum_ccdc_archive 'CCDC 1554455'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-07-21 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 N10 O2, N2 H8'
_chemical_formula_sum            'C3 H10 N12 O2'
_chemical_formula_weight         246.23

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

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

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

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

_cell_length_a                   5.8835(3)
_cell_length_b                   16.3726(7)
_cell_length_c                   10.5070(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.4240(10)
_cell_angle_gamma                90
_cell_volume                     1001.20(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9086
_cell_measurement_theta_min      2.488
_cell_measurement_theta_max      29.981

_exptl_crystal_description       chunk
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.259
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7105
_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            13803
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         29.979
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2823
_reflns_number_gt                2628
_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)+(0.0421P)²+0.3242P] 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         2823
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.41470(12) 0.29274(4) -0.05648(7) 0.02524(16) Uani 1 1 d . . . . .
O2 O 0.26571(13) 0.37732(4) 0.06968(6) 0.02199(15) Uani 1 1 d . . . . .
N3 N 0.26727(13) 0.30912(5) 0.01671(7) 0.01626(15) Uani 1 1 d . . . . .
N4 N 0.12266(13) 0.24946(4) 0.03042(7) 0.01716(15) Uani 1 1 d . . . . .
C5 C -0.03251(14) 0.26285(5) 0.11353(8) 0.01330(15) Uani 1 1 d . . . . .
N6 N -0.08384(13) 0.32461(5) 0.18764(7) 0.01729(15) Uani 1 1 d . . . . .
N7 N -0.25626(14) 0.29598(5) 0.25021(8) 0.02058(16) Uani 1 1 d . . . . .
N8 N -0.31054(13) 0.22148(5) 0.21748(7) 0.01868(16) Uani 1 1 d . . . . .
N9 N -0.17356(12) 0.19989(4) 0.13064(7) 0.01365(14) Uani 1 1 d . . . . .
C10 C -0.17119(14) 0.11724(5) 0.07939(8) 0.01429(15) Uani 1 1 d . . . . .
H10A H -0.1600 0.1195 -0.0136 0.017 Uiso 1 1 calc R U . . .
H10B H -0.3162 0.0891 0.0899 0.017 Uiso 1 1 calc R U . . .
C11 C 0.02859(13) 0.07038(5) 0.14831(7) 0.01258(15) Uani 1 1 d . . . . .
N12 N 0.04640(13) 0.04947(5) 0.27206(7) 0.01756(15) Uani 1 1 d . . . . .
N13 N 0.24887(13) 0.01029(5) 0.29685(7) 0.01841(15) Uani 1 1 d . . . . .
N14 N 0.34662(13) 0.00832(5) 0.19223(7) 0.01718(15) Uani 1 1 d . . . . .
N15 N 0.21032(13) 0.04646(5) 0.09593(7) 0.01617(15) Uani 1 1 d . . . . .
N16 N 0.71057(14) 0.06857(5) 0.44526(7) 0.01741(15) Uani 1 1 d . . . . .
H16B H 0.637(2) 0.1175(9) 0.4368(13) 0.026 Uiso 1 1 d . U . . .
H16D H 0.834(2) 0.0684(8) 0.4007(13) 0.026 Uiso 1 1 d . U . . .
H16C H 0.612(2) 0.0305(9) 0.4098(13) 0.026 Uiso 1 1 d . U . . .
N17 N 0.32160(13) 0.37866(5) 0.35928(7) 0.01667(15) Uani 1 1 d . . . . .
H17A H 0.368(2) 0.3273(9) 0.3784(13) 0.025 Uiso 1 1 d . U . . .
H17B H 0.287(2) 0.4032(8) 0.4310(13) 0.025 Uiso 1 1 d . U . . .
H17D H 0.431(2) 0.4105(8) 0.3328(13) 0.025 Uiso 1 1 d . U . . .
H17C H 0.197(2) 0.3757(8) 0.2992(13) 0.025 Uiso 1 1 d . U . . .
H16A H 0.758(2) 0.0577(8) 0.5262(14) 0.025 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 N3 1.2693(9) . ?
O2 N3 1.2483(10) . ?
N3 N4 1.3171(10) . ?
N4 C5 1.3703(10) . ?
C5 N6 1.3376(10) . ?
C5 N9 1.3517(10) . ?
N6 N7 1.3698(11) . ?
N7 N8 1.2946(11) . ?
N8 N9 1.3499(9) . ?
N9 C10 1.4573(10) . ?
C10 C11 1.4984(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N15 1.3311(10) . ?
C11 N12 1.3338(10) . ?
N12 N13 1.3445(10) . ?
N13 N14 1.3135(10) . ?
N14 N15 1.3487(10) . ?
N16 H16B 0.909(14) . ?
N16 H16D 0.920(14) . ?
N16 H16C 0.896(14) . ?
N16 H16A 0.875(14) . ?
N17 H17A 0.898(14) . ?
N17 H17B 0.903(14) . ?
N17 H17D 0.903(14) . ?
N17 H17C 0.894(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 120.63(7) . . ?
O2 N3 N4 124.58(7) . . ?
O1 N3 N4 114.79(7) . . ?
N3 N4 C5 116.90(7) . . ?
N6 C5 N9 107.68(7) . . ?
N6 C5 N4 136.08(8) . . ?
N9 C5 N4 116.24(7) . . ?
C5 N6 N7 105.48(7) . . ?
N8 N7 N6 111.48(7) . . ?
N7 N8 N9 106.13(7) . . ?
N8 N9 C5 109.22(7) . . ?
N8 N9 C10 122.14(7) . . ?
C5 N9 C10 128.29(7) . . ?
N9 C10 C11 110.25(6) . . ?
N9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N15 C11 N12 111.99(7) . . ?
N15 C11 C10 124.86(7) . . ?
N12 C11 C10 123.13(7) . . ?
C11 N12 N13 104.60(7) . . ?
N14 N13 N12 109.50(7) . . ?
N13 N14 N15 109.35(7) . . ?
C11 N15 N14 104.56(7) . . ?
H16B N16 H16D 110.7(12) . . ?
H16B N16 H16C 107.6(12) . . ?
H16D N16 H16C 107.4(12) . . ?
H16B N16 H16A 110.8(12) . . ?
H16D N16 H16A 109.2(12) . . ?
H16C N16 H16A 111.1(12) . . ?
H17A N17 H17B 109.2(12) . . ?
H17A N17 H17D 113.6(12) . . ?
H17B N17 H17D 104.8(12) . . ?
H17A N17 H17C 107.4(12) . . ?
H17B N17 H17C 110.7(12) . . ?
H17D N17 H17C 111.1(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
O2 N3 N4 C5 -3.12(13) . . . . ?
O1 N3 N4 C5 176.88(7) . . . . ?
N3 N4 C5 N6 1.74(15) . . . . ?
N3 N4 C5 N9 -177.38(7) . . . . ?
N9 C5 N6 N7 0.87(9) . . . . ?
N4 C5 N6 N7 -178.30(10) . . . . ?
C5 N6 N7 N8 -0.24(10) . . . . ?
N6 N7 N8 N9 -0.50(10) . . . . ?
N7 N8 N9 C5 1.05(9) . . . . ?
N7 N8 N9 C10 174.71(7) . . . . ?
N6 C5 N9 N8 -1.21(9) . . . . ?
N4 C5 N9 N8 178.15(7) . . . . ?
N6 C5 N9 C10 -174.37(7) . . . . ?
N4 C5 N9 C10 4.99(12) . . . . ?
N8 N9 C10 C11 -99.20(9) . . . . ?
C5 N9 C10 C11 73.17(10) . . . . ?
N9 C10 C11 N15 -111.32(9) . . . . ?
N9 C10 C11 N12 66.96(10) . . . . ?
N15 C11 N12 N13 -0.35(10) . . . . ?
C10 C11 N12 N13 -178.83(7) . . . . ?
C11 N12 N13 N14 0.13(9) . . . . ?
N12 N13 N14 N15 0.12(10) . . . . ?
N12 C11 N15 N14 0.41(9) . . . . ?
C10 C11 N15 N14 178.86(7) . . . . ?
N13 N14 N15 C11 -0.32(9) . . . . ?

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
N16 H16B O1 0.909(14) 1.975(14) 2.8596(10) 163.9(12) 4_566
N16 H16D N12 0.920(14) 1.995(14) 2.8926(10) 164.8(12) 1_655
N16 H16C O2 0.896(14) 2.610(14) 3.1393(10) 118.7(11) 2_645
N16 H16C N13 0.896(14) 2.309(14) 3.0790(11) 144.0(12) .
N16 H16C N14 0.896(14) 2.597(14) 3.3103(11) 137.1(11) .
N17 H17A O1 0.898(14) 2.086(15) 2.9693(11) 167.5(12) 4_566
N17 H17A N4 0.898(14) 2.627(13) 3.1017(11) 113.9(10) 4_566
N17 H17B N15 0.903(14) 2.029(14) 2.9311(10) 177.5(12) 4_566
N17 H17D N14 0.903(14) 2.109(14) 2.9865(11) 163.8(12) 2_655
N17 H17C O2 0.894(14) 2.503(13) 3.0123(10) 116.7(10) .
N17 H17C N6 0.894(14) 2.060(14) 2.9095(11) 158.3(12) .
N16 H16A N6 0.875(14) 2.644(14) 3.1788(11) 120.5(11) 4_666
N16 H16A N13 0.875(14) 2.172(14) 2.9794(11) 153.2(12) 3_656

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.057

# start Validation Reply Form
_vrf_PLAT015_compd10             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
####################################################################### 
# 
# 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_compd4
_database_code_depnum_ccdc_archive 'CCDC 1554454'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'N-(1-((1H-tetrazol-5-yl)methyl)-1H-tetrazol-5(4H)-ylidene)nitramide '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H4 N10 O2'
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   15.6803(6)
_cell_length_b                   6.6171(3)
_cell_length_c                   17.0112(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.8700(10)
_cell_angle_gamma                90
_cell_volume                     1588.17(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4645
_cell_measurement_theta_min      2.662
_cell_measurement_theta_max      29.966

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7083
_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            9002
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.887
_diffrn_reflns_theta_max         29.970
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2222
_reflns_number_gt                1978
_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)+(0.0424P)²+1.5434P] 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_number_reflns         2222
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0863
_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 0.67623(6) 0.74493(17) 0.61537(6) 0.0306(2) Uani 1 1 d . . . . .
O2 O 0.52760(5) 0.65965(13) 0.55872(5) 0.01762(18) Uani 1 1 d . . . . .
N3 N 0.60467(6) 0.68997(14) 0.62287(6) 0.01523(19) Uani 1 1 d . . . . .
N4 N 0.60552(6) 0.65642(14) 0.70161(5) 0.01446(18) Uani 1 1 d . . . . .
C5 C 0.68969(7) 0.68433(15) 0.77006(6) 0.0129(2) Uani 1 1 d . . . . .
N6 N 0.77858(6) 0.73164(15) 0.78308(6) 0.01579(19) Uani 1 1 d . . . . .
H6 H 0.7964 0.7550 0.7415 0.019 Uiso 1 1 calc R U . . .
N7 N 0.83684(7) 0.73765(16) 0.87093(6) 0.0197(2) Uani 1 1 d . . . . .
N8 N 0.78768(6) 0.69503(16) 0.91202(6) 0.0179(2) Uani 1 1 d . . . . .
N9 N 0.69719(6) 0.65995(14) 0.85171(5) 0.01318(18) Uani 1 1 d . . . . .
C10 C 0.62194(7) 0.60800(16) 0.87644(6) 0.01350(19) Uani 1 1 d . . . . .
H10A H 0.5632 0.6806 0.8382 0.016 Uiso 1 1 calc R U . . .
H10B H 0.6402 0.6507 0.9375 0.016 Uiso 1 1 calc R U . . .
C11 C 0.60406(7) 0.38471(16) 0.86830(6) 0.01246(19) Uani 1 1 d . . . . .
N12 N 0.56330(7) 0.27827(15) 0.90926(6) 0.01701(19) Uani 1 1 d . . . . .
H12 H 0.5421 0.3281 0.9453 0.020 Uiso 1 1 calc R U . . .
N13 N 0.55980(8) 0.08273(16) 0.88666(7) 0.0230(2) Uani 1 1 d . . . . .
N14 N 0.59740(7) 0.07195(15) 0.83259(7) 0.0215(2) Uani 1 1 d . . . . .
N15 N 0.62531(7) 0.25882(14) 0.81920(6) 0.01606(19) 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 1.2380(12) . ?
O2 N3 1.2413(12) . ?
N3 N4 1.3520(11) . ?
N4 C5 1.3382(13) . ?
C5 N6 1.3493(13) . ?
C5 N9 1.3514(12) . ?
N6 N7 1.3704(12) . ?
N6 H6 0.8800 . ?
N7 N8 1.2777(13) . ?
N8 N9 1.3599(12) . ?
N9 C10 1.4563(12) . ?
C10 C11 1.4989(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N15 1.3211(13) . ?
C11 N12 1.3338(13) . ?
N12 N13 1.3442(14) . ?
N12 H12 0.8800 . ?
N13 N14 1.2930(13) . ?
N14 N15 1.3636(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 122.37(9) . . ?
O1 N3 N4 122.19(9) . . ?
O2 N3 N4 115.43(8) . . ?
C5 N4 N3 114.78(8) . . ?
N4 C5 N6 136.96(9) . . ?
N4 C5 N9 119.23(9) . . ?
N6 C5 N9 103.80(8) . . ?
C5 N6 N7 109.58(8) . . ?
C5 N6 H6 125.2 . . ?
N7 N6 H6 125.2 . . ?
N8 N7 N6 108.42(9) . . ?
N7 N8 N9 107.75(8) . . ?
C5 N9 N8 110.45(8) . . ?
C5 N9 C10 127.37(8) . . ?
N8 N9 C10 122.18(8) . . ?
N9 C10 C11 110.39(8) . . ?
N9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N15 C11 N12 107.93(10) . . ?
N15 C11 C10 126.26(9) . . ?
N12 C11 C10 125.81(9) . . ?
C11 N12 N13 109.14(9) . . ?
C11 N12 H12 125.4 . . ?
N13 N12 H12 125.4 . . ?
N14 N13 N12 106.39(9) . . ?
N13 N14 N15 110.37(9) . . ?
C11 N15 N14 106.16(9) . . ?

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 N4 C5 -0.95(16) . . . . ?
O2 N3 N4 C5 178.24(9) . . . . ?
N3 N4 C5 N6 -3.11(19) . . . . ?
N3 N4 C5 N9 178.19(9) . . . . ?
N4 C5 N6 N7 -179.68(12) . . . . ?
N9 C5 N6 N7 -0.84(12) . . . . ?
C5 N6 N7 N8 0.38(13) . . . . ?
N6 N7 N8 N9 0.26(13) . . . . ?
N4 C5 N9 N8 -179.90(9) . . . . ?
N6 C5 N9 N8 1.01(12) . . . . ?
N4 C5 N9 C10 -1.13(16) . . . . ?
N6 C5 N9 C10 179.78(10) . . . . ?
N7 N8 N9 C5 -0.82(13) . . . . ?
N7 N8 N9 C10 -179.67(10) . . . . ?
C5 N9 C10 C11 80.91(13) . . . . ?
N8 N9 C10 C11 -100.45(11) . . . . ?
N9 C10 C11 N15 -22.28(14) . . . . ?
N9 C10 C11 N12 158.08(10) . . . . ?
N15 C11 N12 N13 0.76(12) . . . . ?
C10 C11 N12 N13 -179.55(9) . . . . ?
C11 N12 N13 N14 -0.33(13) . . . . ?
N12 N13 N14 N15 -0.21(13) . . . . ?
N12 C11 N15 N14 -0.85(12) . . . . ?
C10 C11 N15 N14 179.45(9) . . . . ?
N13 N14 N15 C11 0.67(13) . . . . ?

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 H6 O1 0.88 2.15 2.5937(13) 110.4 .
N6 H6 N15 0.88 1.92 2.7603(12) 159.6 4_656
N12 H12 O2 0.88 2.44 3.0617(13) 128.2 2_656
N12 H12 O2 0.88 2.04 2.8614(12) 155.0 6_566

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.051

# start Validation Reply Form
_vrf_PLAT430_compd4              
;
PROBLEM: Short Inter D...A Contact  O1     ..  N15     ..       2.81 Ang.  
RESPONSE: Close contacts are common in high-density energetic materials.
;
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT015_compd4              
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    ', Impact and Friction Sensitivity'
####################################################################### 
# 
# 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_compd13
_database_code_depnum_ccdc_archive 'CCDC 1554456'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-07-21 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 N10 O2, 2(C3 H7 N8)'
_chemical_formula_sum            'C9 H16 N26 O2'
_chemical_formula_weight         520.48

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                   6.8412(2)
_cell_length_b                   16.3568(4)
_cell_length_c                   17.7892(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.2720(10)
_cell_angle_gamma                90
_cell_volume                     1990.12(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8927
_cell_measurement_theta_min      2.491
_cell_measurement_theta_max      29.905

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.105
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7087
_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            23403
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         29.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5613
_reflns_number_gt                4696
_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)+(0.0532P)²+0.6089P] 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         5613
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70511(14) 0.80295(5) 0.99564(5) 0.02233(19) Uani 1 1 d . . . . .
O2 O 0.74244(14) 0.93496(5) 0.99702(5) 0.02297(19) Uani 1 1 d . . . . .
N3 N 0.75206(14) 0.86777(6) 0.96314(5) 0.01591(19) Uani 1 1 d . . . . .
N4 N 0.80873(14) 0.85946(6) 0.89271(5) 0.01661(19) Uani 1 1 d . . . . .
C5 C 0.86551(15) 0.92981(7) 0.85776(6) 0.0141(2) Uani 1 1 d . . . . .
N6 N 0.88113(15) 1.00779(6) 0.87893(6) 0.0181(2) Uani 1 1 d . . . . .
N7 N 0.94099(15) 1.04874(6) 0.81683(6) 0.0198(2) Uani 1 1 d . . . . .
N8 N 0.96303(14) 1.00040(6) 0.76017(6) 0.0182(2) Uani 1 1 d . . . . .
N9 N 0.91923(13) 0.92455(5) 0.78502(5) 0.01461(18) Uani 1 1 d . . . . .
C10 C 0.90498(17) 0.85366(7) 0.73437(6) 0.0166(2) Uani 1 1 d . . . . .
H10A H 0.7761 0.8541 0.7080 0.020 Uiso 1 1 calc R U . . .
H10B H 0.9147 0.8027 0.7643 0.020 Uiso 1 1 calc R U . . .
C11 C 1.06315(16) 0.85485(6) 0.67787(6) 0.0147(2) Uani 1 1 d . . . . .
N12 N 1.07245(15) 0.90657(6) 0.62024(5) 0.0190(2) Uani 1 1 d . . . . .
N13 N 1.23959(15) 0.88660(6) 0.58624(6) 0.0204(2) Uani 1 1 d . . . . .
N14 N 1.32377(15) 0.82531(6) 0.62221(5) 0.0192(2) Uani 1 1 d . . . . .
N15 N 1.21451(14) 0.80320(6) 0.68054(5) 0.01675(19) Uani 1 1 d . . . . .
N16 N 0.62227(16) 0.70368(7) 0.60400(6) 0.0205(2) Uani 1 1 d . . . . .
H16A H 0.594(2) 0.6632(10) 0.6323(9) 0.025 Uiso 1 1 d . U . . .
H16B H 0.549(2) 0.7481(10) 0.6080(9) 0.025 Uiso 1 1 d . U . . .
C17 C 0.68862(16) 0.68798(7) 0.53567(6) 0.0150(2) Uani 1 1 d . . . . .
N18 N 0.73879(14) 0.74506(6) 0.48494(5) 0.01473(18) Uani 1 1 d . . . . .
N19 N 0.75313(14) 0.83010(6) 0.48145(6) 0.01701(19) Uani 1 1 d . . . . .
C20 C 0.82936(16) 0.83990(7) 0.41462(6) 0.0159(2) Uani 1 1 d . . . . .
N21 N 0.86515(15) 0.91143(6) 0.38148(6) 0.0227(2) Uani 1 1 d . . . . .
H21A H 0.8373 0.9574 0.4045 0.027 Uiso 1 1 calc R U . . .
H21B H 0.9165 0.9126 0.3366 0.027 Uiso 1 1 calc R U . . .
N22 N 0.86517(14) 0.76665(6) 0.37692(5) 0.01541(18) Uani 1 1 d . . . . .
N23 N 0.96252(16) 0.76297(7) 0.30901(6) 0.0212(2) Uani 1 1 d . . . . .
H23A H 0.886(3) 0.7385(11) 0.2762(10) 0.036(5) Uiso 1 1 d . . . . .
H23B H 1.076(3) 0.7341(11) 0.3168(10) 0.041(5) Uiso 1 1 d . . . . .
C24 C 0.80778(15) 0.70588(7) 0.42398(6) 0.0138(2) Uani 1 1 d . . . . .
N25 N 0.80457(14) 0.62593(6) 0.42960(5) 0.01543(19) Uani 1 1 d . . . . .
N26 N 0.72614(14) 0.61654(6) 0.50164(5) 0.01600(19) Uani 1 1 d . . . . .
H26 H 0.7039 0.5686 0.5223 0.019 Uiso 1 1 calc R U . . .
N27 N 0.39240(16) 1.12759(6) 0.85841(6) 0.0218(2) Uani 1 1 d . . . . .
H27A H 0.3531 1.1124 0.9031 0.026 Uiso 1 1 calc R U . . .
H27B H 0.4055 1.1798 0.8479 0.026 Uiso 1 1 calc R U . . .
C28 C 0.43183(15) 1.07185(7) 0.80711(6) 0.0144(2) Uani 1 1 d . . . . .
N29 N 0.49833(13) 1.08593(5) 0.73765(5) 0.01424(18) Uani 1 1 d . . . . .
N30 N 0.55562(14) 1.15289(6) 0.69470(5) 0.01568(18) Uani 1 1 d . . . . .
C31 C 0.61839(15) 1.11557(6) 0.63334(6) 0.0137(2) Uani 1 1 d . . . . .
N32 N 0.69375(14) 1.15138(6) 0.57387(5) 0.01777(19) Uani 1 1 d . . . . .
H32A H 0.7060 1.2049 0.5726 0.021 Uiso 1 1 calc R U . . .
H32B H 0.7316 1.1216 0.5356 0.021 Uiso 1 1 calc R U . . .
N33 N 0.60410(14) 1.03050(6) 0.63617(5) 0.01451(18) Uani 1 1 d . . . . .
N34 N 0.65849(16) 0.98067(6) 0.57635(6) 0.01793(19) Uani 1 1 d . . . . .
H34A H 0.767(2) 0.9527(10) 0.5889(9) 0.022 Uiso 1 1 d . U . . .
H34B H 0.564(2) 0.9470(10) 0.5656(9) 0.022 Uiso 1 1 d . U . . .
C35 C 0.52730(15) 1.01208(6) 0.70456(6) 0.0136(2) Uani 1 1 d . . . . .
N36 N 0.48365(14) 0.94961(6) 0.74667(5) 0.01614(19) Uani 1 1 d . . . . .
N37 N 0.42126(14) 0.99012(6) 0.81194(5) 0.01555(19) Uani 1 1 d . . . . .
H37 H 0.3795 0.9643 0.8519 0.019 Uiso 1 1 calc R 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 1.2530(12) . ?
O2 N3 1.2559(12) . ?
N3 N4 1.3267(13) . ?
N4 C5 1.3683(14) . ?
C5 N6 1.3336(14) . ?
C5 N9 1.3556(14) . ?
N6 N7 1.3627(14) . ?
N7 N8 1.2925(14) . ?
N8 N9 1.3530(13) . ?
N9 C10 1.4704(14) . ?
C10 C11 1.4932(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.3316(14) . ?
C11 N15 1.3364(14) . ?
N12 N13 1.3456(14) . ?
N13 N14 1.3153(14) . ?
N14 N15 1.3418(13) . ?
N16 C17 1.3320(14) . ?
N16 H16A 0.856(17) . ?
N16 H16B 0.885(17) . ?
C17 N26 1.3434(14) . ?
C17 N18 1.3482(14) . ?
N18 C24 1.3535(14) . ?
N18 N19 1.3960(12) . ?
N19 C20 1.3185(15) . ?
C20 N21 1.3352(14) . ?
C20 N22 1.3975(14) . ?
N21 H21A 0.8800 . ?
N21 H21B 0.8800 . ?
N22 C24 1.3629(14) . ?
N22 N23 1.3936(13) . ?
N23 H23A 0.872(19) . ?
N23 H23B 0.915(19) . ?
C24 N25 1.3117(14) . ?
N25 N26 1.4087(13) . ?
N26 H26 0.8800 . ?
N27 C28 1.3219(14) . ?
N27 H27A 0.8800 . ?
N27 H27B 0.8800 . ?
C28 N37 1.3418(14) . ?
C28 N29 1.3461(13) . ?
N29 C35 1.3602(13) . ?
N29 N30 1.3965(12) . ?
N30 C31 1.3301(14) . ?
C31 N32 1.3237(14) . ?
C31 N33 1.3958(14) . ?
N32 H32A 0.8800 . ?
N32 H32B 0.8800 . ?
N33 C35 1.3694(14) . ?
N33 N34 1.3976(13) . ?
N34 H34A 0.899(16) . ?
N34 H34B 0.867(16) . ?
C35 N36 1.3055(14) . ?
N36 N37 1.4112(13) . ?
N37 H37 0.8800 . ?

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 120.15(9) . . ?
O1 N3 N4 115.62(9) . . ?
O2 N3 N4 124.23(9) . . ?
N3 N4 C5 115.77(9) . . ?
N6 C5 N9 107.97(9) . . ?
N6 C5 N4 134.25(10) . . ?
N9 C5 N4 117.77(9) . . ?
C5 N6 N7 105.35(9) . . ?
N8 N7 N6 111.95(9) . . ?
N7 N8 N9 106.00(9) . . ?
N8 N9 C5 108.68(9) . . ?
N8 N9 C10 122.35(9) . . ?
C5 N9 C10 128.26(9) . . ?
N9 C10 C11 111.28(9) . . ?
N9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N12 C11 N15 112.25(10) . . ?
N12 C11 C10 125.05(10) . . ?
N15 C11 C10 122.70(10) . . ?
C11 N12 N13 104.33(9) . . ?
N14 N13 N12 109.48(9) . . ?
N13 N14 N15 109.65(9) . . ?
C11 N15 N14 104.28(9) . . ?
C17 N16 H16A 118.3(11) . . ?
C17 N16 H16B 115.8(10) . . ?
H16A N16 H16B 116.9(14) . . ?
N16 C17 N26 130.64(10) . . ?
N16 C17 N18 125.05(10) . . ?
N26 C17 N18 104.28(9) . . ?
C17 N18 C24 107.87(9) . . ?
C17 N18 N19 137.64(9) . . ?
C24 N18 N19 114.21(9) . . ?
C20 N19 N18 101.00(9) . . ?
N19 C20 N21 125.79(11) . . ?
N19 C20 N22 113.92(9) . . ?
N21 C20 N22 120.24(11) . . ?
C20 N21 H21A 120.0 . . ?
C20 N21 H21B 120.0 . . ?
H21A N21 H21B 120.0 . . ?
C24 N22 N23 130.59(9) . . ?
C24 N22 C20 105.94(9) . . ?
N23 N22 C20 123.04(9) . . ?
N22 N23 H23A 108.1(12) . . ?
N22 N23 H23B 108.0(11) . . ?
H23A N23 H23B 111.0(16) . . ?
N25 C24 N18 113.84(10) . . ?
N25 C24 N22 141.21(10) . . ?
N18 C24 N22 104.90(9) . . ?
C24 N25 N26 100.69(9) . . ?
C17 N26 N25 113.30(9) . . ?
C17 N26 H26 123.4 . . ?
N25 N26 H26 123.4 . . ?
C28 N27 H27A 120.0 . . ?
C28 N27 H27B 120.0 . . ?
H27A N27 H27B 120.0 . . ?
N27 C28 N37 129.11(10) . . ?
N27 C28 N29 126.44(10) . . ?
N37 C28 N29 104.42(9) . . ?
C28 N29 C35 107.51(9) . . ?
C28 N29 N30 137.82(9) . . ?
C35 N29 N30 114.48(9) . . ?
C31 N30 N29 100.88(8) . . ?
N32 C31 N30 126.26(10) . . ?
N32 C31 N33 119.92(10) . . ?
N30 C31 N33 113.80(9) . . ?
C31 N32 H32A 120.0 . . ?
C31 N32 H32B 120.0 . . ?
H32A N32 H32B 120.0 . . ?
C35 N33 C31 106.27(9) . . ?
C35 N33 N34 131.45(9) . . ?
C31 N33 N34 122.27(9) . . ?
N33 N34 H34A 109.9(10) . . ?
N33 N34 H34B 109.3(10) . . ?
H34A N34 H34B 109.9(14) . . ?
N36 C35 N29 114.17(10) . . ?
N36 C35 N33 141.18(10) . . ?
N29 C35 N33 104.56(9) . . ?
C35 N36 N37 100.48(8) . . ?
C28 N37 N36 113.42(9) . . ?
C28 N37 H37 123.3 . . ?
N36 N37 H37 123.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 N4 C5 -178.18(9) . . . . ?
O2 N3 N4 C5 2.35(16) . . . . ?
N3 N4 C5 N6 1.38(19) . . . . ?
N3 N4 C5 N9 -178.14(9) . . . . ?
N9 C5 N6 N7 1.29(12) . . . . ?
N4 C5 N6 N7 -178.27(12) . . . . ?
C5 N6 N7 N8 -0.32(13) . . . . ?
N6 N7 N8 N9 -0.78(13) . . . . ?
N7 N8 N9 C5 1.58(12) . . . . ?
N7 N8 N9 C10 172.71(10) . . . . ?
N6 C5 N9 N8 -1.81(12) . . . . ?
N4 C5 N9 N8 177.83(9) . . . . ?
N6 C5 N9 C10 -172.26(10) . . . . ?
N4 C5 N9 C10 7.39(16) . . . . ?
N8 N9 C10 C11 40.87(14) . . . . ?
C5 N9 C10 C11 -149.86(11) . . . . ?
N9 C10 C11 N12 -71.56(14) . . . . ?
N9 C10 C11 N15 107.81(12) . . . . ?
N15 C11 N12 N13 -0.92(13) . . . . ?
C10 C11 N12 N13 178.52(10) . . . . ?
C11 N12 N13 N14 0.45(12) . . . . ?
N12 N13 N14 N15 0.15(13) . . . . ?
N12 C11 N15 N14 1.00(13) . . . . ?
C10 C11 N15 N14 -178.44(10) . . . . ?
N13 N14 N15 C11 -0.68(12) . . . . ?
N16 C17 N18 C24 177.13(11) . . . . ?
N26 C17 N18 C24 -1.38(12) . . . . ?
N16 C17 N18 N19 3.8(2) . . . . ?
N26 C17 N18 N19 -174.71(12) . . . . ?
C17 N18 N19 C20 174.58(13) . . . . ?
C24 N18 N19 C20 1.54(12) . . . . ?
N18 N19 C20 N21 176.64(11) . . . . ?
N18 N19 C20 N22 -0.68(12) . . . . ?
N19 C20 N22 C24 -0.33(13) . . . . ?
N21 C20 N22 C24 -177.82(10) . . . . ?
N19 C20 N22 N23 -173.54(10) . . . . ?
N21 C20 N22 N23 8.97(16) . . . . ?
C17 N18 C24 N25 1.08(13) . . . . ?
N19 N18 C24 N25 176.15(9) . . . . ?
C17 N18 C24 N22 -176.87(9) . . . . ?
N19 N18 C24 N22 -1.79(12) . . . . ?
N23 N22 C24 N25 -3.3(2) . . . . ?
C20 N22 C24 N25 -175.78(14) . . . . ?
N23 N22 C24 N18 173.72(11) . . . . ?
C20 N22 C24 N18 1.23(11) . . . . ?
N18 C24 N25 N26 -0.26(12) . . . . ?
N22 C24 N25 N26 176.57(14) . . . . ?
N16 C17 N26 N25 -177.09(11) . . . . ?
N18 C17 N26 N25 1.30(12) . . . . ?
C24 N25 N26 C17 -0.67(12) . . . . ?
N27 C28 N29 C35 177.44(11) . . . . ?
N37 C28 N29 C35 -0.91(12) . . . . ?
N27 C28 N29 N30 3.0(2) . . . . ?
N37 C28 N29 N30 -175.36(12) . . . . ?
C28 N29 N30 C31 175.00(12) . . . . ?
C35 N29 N30 C31 0.82(12) . . . . ?
N29 N30 C31 N32 -178.59(10) . . . . ?
N29 N30 C31 N33 -0.30(12) . . . . ?
N32 C31 N33 C35 178.13(10) . . . . ?
N30 C31 N33 C35 -0.28(12) . . . . ?
N32 C31 N33 N34 -3.11(16) . . . . ?
N30 C31 N33 N34 178.48(10) . . . . ?
C28 N29 C35 N36 0.47(13) . . . . ?
N30 N29 C35 N36 176.38(9) . . . . ?
C28 N29 C35 N33 -176.92(9) . . . . ?
N30 N29 C35 N33 -1.01(12) . . . . ?
C31 N33 C35 N36 -175.46(14) . . . . ?
N34 N33 C35 N36 5.9(2) . . . . ?
C31 N33 C35 N29 0.74(11) . . . . ?
N34 N33 C35 N29 -177.86(11) . . . . ?
N29 C35 N36 N37 0.17(12) . . . . ?
N33 C35 N36 N37 176.14(14) . . . . ?
N27 C28 N37 N36 -177.20(11) . . . . ?
N29 C28 N37 N36 1.09(12) . . . . ?
C35 N36 N37 C28 -0.79(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
N16 H16A N6 0.856(17) 2.556(17) 3.2186(14) 135.0(14) 2_646
N16 H16A N7 0.856(17) 2.096(17) 2.9361(15) 166.9(15) 2_646
N16 H16B N14 0.885(17) 2.014(17) 2.8744(14) 163.6(14) 1_455
N21 H21A N13 0.88 2.61 3.4315(15) 155.6 3_776
N21 H21A N12 0.88 2.35 3.0078(14) 131.4 3_776
N21 H21B N8 0.88 2.39 3.1532(15) 144.7 3_776
N23 H23A N15 0.872(19) 2.157(19) 3.0168(15) 168.9(16) 4_575
N23 H23B N4 0.915(19) 2.571(19) 3.4176(15) 154.1(15) 4_675
N26 H26 O2 0.88 2.24 2.9778(13) 140.6 2_646
N26 H26 N6 0.88 2.11 2.8784(13) 145.1 2_646
N27 H27A O1 0.88 2.31 2.9247(13) 126.6 3_677
N27 H27A O2 0.88 2.06 2.9355(13) 174.1 3_677
N27 H27A N3 0.88 2.52 3.3466(14) 156.2 3_677
N27 H27B N15 0.88 2.23 3.0403(14) 152.6 2_656
N32 H32A O1 0.88 2.11 2.8623(13) 143.2 2_656
N32 H32A N4 0.88 2.60 3.4551(14) 162.8 2_656
N32 H32B N13 0.88 2.19 2.9604(14) 146.7 3_776
N34 H34A N12 0.899(16) 2.277(16) 3.1624(15) 168.6(14) .
N34 H34B N13 0.867(16) 2.465(16) 3.2608(15) 152.9(14) 1_455
N37 H37 N25 0.88 2.09 2.9488(13) 163.8 4_576

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.068

# start Validation Reply Form
_vrf_PLAT015_compd13             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
####################################################################### 
# 
# 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_Compd2
_database_code_depnum_ccdc_archive 'CCDC 1554453'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-((1H-tetrazol-5-yl)methyl)-1H-tetrazol-5-amine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H5 N9'
_chemical_formula_sum            'C3 H5 N9'
_chemical_formula_weight         167.16

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'

_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                   4.940(3)
_cell_length_b                   5.906(4)
_cell_length_c                   12.109(7)
_cell_angle_alpha                97.538(9)
_cell_angle_beta                 90.277(8)
_cell_angle_gamma                105.359(9)
_cell_volume                     337.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1108
_cell_measurement_theta_min      3.397
_cell_measurement_theta_max      25.994

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.641986
_exptl_absorpt_correction_T_max  0.745370
_exptl_absorpt_process_details   'TWINABS v2012/1 (Bruker, 2005)'
_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            1164
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         26.066
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             1164
_reflns_number_gt                1105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+0.0778P] 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         1164
_refine_ls_number_parameters     116
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.107
_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 0.7854(4) 0.1848(3) 0.42264(15) 0.0246(4) Uani 1 1 d D . . . .
H1A H 0.923(4) 0.216(4) 0.4751(16) 0.030 Uiso 1 1 d D U . . .
H1B H 0.725(5) 0.296(4) 0.3972(18) 0.030 Uiso 1 1 d D U . . .
C2 C 0.6748(4) -0.0415(4) 0.38286(14) 0.0175(4) Uani 1 1 d . . . . .
N4 N 0.5821(4) -0.4205(3) 0.35092(15) 0.0273(4) Uani 1 1 d . . . . .
N3 N 0.7556(3) -0.2252(3) 0.41150(14) 0.0225(4) Uani 1 1 d . . . . .
N6 N 0.4588(3) -0.1274(3) 0.30678(12) 0.0173(4) Uani 1 1 d . . . . .
N5 N 0.4052(4) -0.3682(3) 0.28695(15) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.3141(4) -0.0020(4) 0.24090(15) 0.0178(4) Uani 1 1 d . . . . .
H7A H 0.2466 0.1163 0.2909 0.021 Uiso 1 1 calc R U . . .
H7B H 0.1491 -0.1157 0.2000 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5093(4) 0.1204(3) 0.15975(14) 0.0150(4) Uani 1 1 d . . . . .
N9 N 0.4496(3) 0.2559(3) 0.08807(12) 0.0172(4) Uani 1 1 d . . . . .
H9 H 0.2852 0.2838 0.0786 0.021 Uiso 1 1 calc R U . . .
N11 N 0.8748(3) 0.2588(3) 0.07096(14) 0.0218(4) Uani 1 1 d . . . . .
N10 N 0.6813(3) 0.3426(3) 0.03284(13) 0.0208(4) Uani 1 1 d . . . . .
N12 N 0.7741(3) 0.1180(3) 0.15071(13) 0.0201(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.326(3) . ?
C2 N3 1.336(2) . ?
C2 N6 1.351(2) . ?
N4 N5 1.288(2) . ?
N4 N3 1.361(3) . ?
N6 N5 1.364(2) . ?
N6 C7 1.458(2) . ?
C7 C8 1.498(3) . ?
C8 N12 1.317(2) . ?
C8 N9 1.336(2) . ?
N9 N10 1.344(2) . ?
N11 N10 1.296(2) . ?
N11 N12 1.367(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
N1 C2 N3 126.09(18) . . ?
N1 C2 N6 126.09(17) . . ?
N3 C2 N6 107.82(18) . . ?
N5 N4 N3 112.51(16) . . ?
C2 N3 N4 105.36(16) . . ?
C2 N6 N5 108.91(15) . . ?
C2 N6 C7 129.91(17) . . ?
N5 N6 C7 120.78(15) . . ?
N4 N5 N6 105.39(16) . . ?
N6 C7 C8 110.07(15) . . ?
N12 C8 N9 108.75(16) . . ?
N12 C8 C7 124.85(15) . . ?
N9 C8 C7 126.36(15) . . ?
C8 N9 N10 108.92(14) . . ?
N10 N11 N12 111.09(15) . . ?
N11 N10 N9 105.95(14) . . ?
C8 N12 N11 105.29(14) . . ?

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 179.35(19) . . . . ?
N6 C2 N3 N4 -0.2(2) . . . . ?
N5 N4 N3 C2 0.8(2) . . . . ?
N1 C2 N6 N5 -179.98(19) . . . . ?
N3 C2 N6 N5 -0.5(2) . . . . ?
N1 C2 N6 C7 7.4(3) . . . . ?
N3 C2 N6 C7 -173.04(17) . . . . ?
N3 N4 N5 N6 -1.1(2) . . . . ?
C2 N6 N5 N4 0.9(2) . . . . ?
C7 N6 N5 N4 174.31(16) . . . . ?
C2 N6 C7 C8 66.5(2) . . . . ?
N5 N6 C7 C8 -105.3(2) . . . . ?
N6 C7 C8 N12 -1.1(3) . . . . ?
N6 C7 C8 N9 -178.39(18) . . . . ?
N12 C8 N9 N10 -0.4(2) . . . . ?
C7 C8 N9 N10 177.30(18) . . . . ?
N12 N11 N10 N9 0.0(2) . . . . ?
C8 N9 N10 N11 0.3(2) . . . . ?
N9 C8 N12 N11 0.4(2) . . . . ?
C7 C8 N12 N11 -177.38(17) . . . . ?
N10 N11 N12 C8 -0.2(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
N1 H1A N3 0.893(16) 2.080(16) 2.962(3) 170(2) 2_756
N1 H1B N4 0.879(16) 2.117(16) 2.994(3) 175(2) 1_565
N9 H9 N11 0.88 1.99 2.851(3) 164.0 1_455

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040

# start Validation Reply Form
_vrf_PLAT029_Compd2              
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.916 Note  
RESPONSE: Low data completeness results from the low symmetry P-1 space group.
;
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT015_Compd2              
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
