# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_kx389
_database_code_depnum_ccdc_archive 'CCDC 1501785'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-03-12 downloaded from the CCDC.
;
_audit_creation_date             
;
'Wed Oct 21 15:34:53 2015'
;
_audit_creation_method           SHELXL-2013


_chemical_name_systematic        
;
5-trinitromethyl-3-nitraminotriazole
;
_chemical_name_common            5-trinitromethyl-3-nitraminotriazole
_chemical_compound_source        ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H2 N8 O8'
_chemical_formula_sum            'C3 H2 N8 O8'
_chemical_formula_weight         278.13

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_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                   9.1597(7)
_cell_length_b                   10.5684(7)
_cell_length_c                   9.9433(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.110(7)
_cell_angle_gamma                90
_cell_volume                     944.51(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2868
_cell_measurement_theta_min      4.6330
_cell_measurement_theta_max      31.1480

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93286
_exptl_absorpt_correction_T_max  0.99999
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?



_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            7214
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.386
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1958
_reflns_number_gt                1746
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+0.3625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?

_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1958
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3



_diffrn_orient_matrix_UB_11      0.0187817000
_diffrn_orient_matrix_UB_12      0.0055276000
_diffrn_orient_matrix_UB_13      -0.0656706000
_diffrn_orient_matrix_UB_21      -0.0073588000
_diffrn_orient_matrix_UB_22      -0.0664465000
_diffrn_orient_matrix_UB_23      -0.0088768000
_diffrn_orient_matrix_UB_31      -0.0762835000
_diffrn_orient_matrix_UB_32      0.0077825000
_diffrn_orient_matrix_UB_33      -0.0299429000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   96.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -19.0000   60.0000 142

#__ type_ start__ end____ width___ exp.time_
  2 omega   53.00   81.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   57.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   40.00  109.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000  -30.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   75.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   73.00  111.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932 -179.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega -101.00   -3.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -77.0000   60.0000 98

;



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'


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 0.66140(13) -0.23453(10) 0.73795(11) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.66412(15) -0.30415(11) 0.94459(11) 0.0405(3) Uani 1 1 d . . . . .
O3 O 0.53941(13) 0.34885(12) 0.52703(11) 0.0388(3) Uani 1 1 d . . . . .
O4 O 0.30735(13) 0.39513(12) 0.52530(11) 0.0413(3) Uani 1 1 d . . . . .
O5 O 0.28902(14) 0.44027(11) 0.80897(12) 0.0418(3) Uani 1 1 d . . . . .
O6 O 0.21095(12) 0.24781(12) 0.75906(13) 0.0415(3) Uani 1 1 d . . . . .
O7 O 0.60805(16) 0.47741(12) 0.76459(14) 0.0521(4) Uani 1 1 d . . . . .
O8 O 0.60829(13) 0.34312(12) 0.92938(11) 0.0385(3) Uani 1 1 d . . . . .
N1 N 0.53535(13) -0.01420(12) 0.66610(12) 0.0234(3) Uani 1 1 d . . . . .
N2 N 0.49885(13) 0.10364(11) 0.61697(11) 0.0230(3) Uani 1 1 d . . . . .
N3 N 0.50208(12) 0.09486(11) 0.84495(11) 0.0205(3) Uani 1 1 d . . . . .
N4 N 0.56685(14) -0.11894(11) 0.88691(12) 0.0262(3) Uani 1 1 d . . . . .
N5 N 0.63488(14) -0.22617(11) 0.85383(12) 0.0263(3) Uani 1 1 d . . . . .
N6 N 0.42915(14) 0.35424(12) 0.57693(13) 0.0284(3) Uani 1 1 d . . . . .
N7 N 0.30160(14) 0.33278(13) 0.77010(13) 0.0298(3) Uani 1 1 d . . . . .
N8 N 0.56720(14) 0.38309(12) 0.81561(13) 0.0284(3) Uani 1 1 d . . . . .
C1 C 0.53693(14) -0.01698(13) 0.80058(13) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.48144(14) 0.16456(13) 0.72779(13) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.44689(15) 0.30234(13) 0.72316(13) 0.0225(3) Uani 1 1 d . . . . .
H1 H 0.5507(19) -0.0739(18) 0.6138(19) 0.030(4) Uiso 1 1 d . . . . .
H2 H 0.549(2) -0.1170(17) 0.969(2) 0.034(5) Uiso 1 1 d . . . . .


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 N5 1.2257(15) . ?
O2 N5 1.2133(16) . ?
O3 N6 1.2094(17) . ?
O4 N6 1.2142(17) . ?
O5 N7 1.2126(18) . ?
O6 N7 1.2135(17) . ?
O7 N8 1.2100(17) . ?
O8 N8 1.1982(17) . ?
N1 C1 1.3347(17) . ?
N1 N2 1.3558(16) . ?
N1 H1 0.85(2) . ?
N2 C2 1.3123(17) . ?
N3 C1 1.3220(17) . ?
N3 C2 1.3604(17) . ?
N4 N5 1.3637(17) . ?
N4 C1 1.3721(18) . ?
N4 H2 0.858(19) . ?
N6 C3 1.5330(18) . ?
N7 C3 1.5271(18) . ?
N8 C3 1.5483(18) . ?
C2 C3 1.4889(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 109.61(11) . . ?
C1 N1 H1 128.9(12) . . ?
N2 N1 H1 121.4(12) . . ?
C2 N2 N1 102.09(11) . . ?
C1 N3 C2 101.59(11) . . ?
N5 N4 C1 123.18(12) . . ?
N5 N4 H2 115.2(12) . . ?
C1 N4 H2 121.5(12) . . ?
O2 N5 O1 126.51(13) . . ?
O2 N5 N4 115.51(12) . . ?
O1 N5 N4 117.98(12) . . ?
O3 N6 O4 127.96(13) . . ?
O3 N6 C3 115.34(12) . . ?
O4 N6 C3 116.69(12) . . ?
O5 N7 O6 128.08(13) . . ?
O5 N7 C3 115.89(13) . . ?
O6 N7 C3 115.97(12) . . ?
O8 N8 O7 128.31(14) . . ?
O8 N8 C3 115.11(12) . . ?
O7 N8 C3 116.57(12) . . ?
N3 C1 N1 110.97(12) . . ?
N3 C1 N4 121.69(12) . . ?
N1 C1 N4 127.33(12) . . ?
N2 C2 N3 115.73(12) . . ?
N2 C2 C3 120.89(12) . . ?
N3 C2 C3 123.35(12) . . ?
C2 C3 N7 112.90(11) . . ?
C2 C3 N6 111.24(11) . . ?
N7 C3 N6 105.97(11) . . ?
C2 C3 N8 113.45(11) . . ?
N7 C3 N8 105.36(11) . . ?
N6 C3 N8 107.41(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 0.28(14) . . . . ?
C1 N4 N5 O2 174.55(13) . . . . ?
C1 N4 N5 O1 -4.9(2) . . . . ?
C2 N3 C1 N1 -0.69(15) . . . . ?
C2 N3 C1 N4 -179.62(12) . . . . ?
N2 N1 C1 N3 0.28(16) . . . . ?
N2 N1 C1 N4 179.14(13) . . . . ?
N5 N4 C1 N3 -164.68(13) . . . . ?
N5 N4 C1 N1 16.6(2) . . . . ?
N1 N2 C2 N3 -0.77(15) . . . . ?
N1 N2 C2 C3 177.04(12) . . . . ?
C1 N3 C2 N2 0.93(15) . . . . ?
C1 N3 C2 C3 -176.82(12) . . . . ?
N2 C2 C3 N7 121.62(13) . . . . ?
N3 C2 C3 N7 -60.75(17) . . . . ?
N2 C2 C3 N6 2.63(17) . . . . ?
N3 C2 C3 N6 -179.74(11) . . . . ?
N2 C2 C3 N8 -118.60(13) . . . . ?
N3 C2 C3 N8 59.03(17) . . . . ?
O5 N7 C3 C2 158.14(12) . . . . ?
O6 N7 C3 C2 -24.50(17) . . . . ?
O5 N7 C3 N6 -79.86(14) . . . . ?
O6 N7 C3 N6 97.50(14) . . . . ?
O5 N7 C3 N8 33.80(15) . . . . ?
O6 N7 C3 N8 -148.84(12) . . . . ?
O3 N6 C3 C2 -63.36(16) . . . . ?
O4 N6 C3 C2 116.45(14) . . . . ?
O3 N6 C3 N7 173.58(12) . . . . ?
O4 N6 C3 N7 -6.61(16) . . . . ?
O3 N6 C3 N8 61.34(15) . . . . ?
O4 N6 C3 N8 -118.85(13) . . . . ?
O8 N8 C3 C2 -46.76(17) . . . . ?
O7 N8 C3 C2 133.00(14) . . . . ?
O8 N8 C3 N7 77.23(15) . . . . ?
O7 N8 C3 N7 -103.02(15) . . . . ?
O8 N8 C3 N6 -170.11(12) . . . . ?
O7 N8 C3 N6 9.64(17) . . . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

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 H1 N2 0.85(2) 2.273(19) 2.9282(17) 134.3(15) 3_656
N4 H2 N3 0.858(19) 2.01(2) 2.8671(17) 174.0(17) 3_657
N1 H1 N2 0.85(2) 2.273(19) 2.9282(17) 134.3(15) 3_656
N4 H2 N3 0.858(19) 2.01(2) 2.8671(17) 174.0(17) 3_657

_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.
;



_refine_diff_density_max         0.344
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4


