#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:55:50 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/63/7236383.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7236383
loop_
_publ_author_name
'Xu, Yuangang'
'Shen, Cheng'
'Lin, Qiuhan'
'Wang, Pengcheng'
'Jiang, Chao'
'Lu, Ming'
_publ_section_title
;
 1-Nitro-2-trinitromethyl substituted imidazoles: a new family of high
 performance energetic materials
;
_journal_issue                   45
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              17791
_journal_paper_doi               10.1039/C6TA08831G
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C8 H8 N6 O12'
_chemical_formula_weight         380.20
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                86.59(3)
_cell_angle_beta                 89.54(3)
_cell_angle_gamma                72.16(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6990(17)
_cell_length_b                   8.7890(18)
_cell_length_c                   10.723(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     779.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3069
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.3300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1889
_reflns_number_gt                1833
_reflns_number_total             2867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ta08831g2.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7236383
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.1125(3) 0.6464(3) 0.1801(2) 0.0509(6) Uani 1 1 d .
N1 N -0.1653(3) 0.9646(3) 0.2098(3) 0.0486(7) Uani 1 1 d .
C1 C 0.0156(4) 0.7255(4) 0.2779(3) 0.0449(8) Uani 1 1 d .
H1A H 0.0207 0.6526 0.3516 0.054 Uiso 1 1 calc R
N2 N 0.0741(3) 0.8594(3) 0.3065(2) 0.0448(7) Uani 1 1 d .
C2 C -0.1582(4) 0.7981(4) 0.2283(3) 0.0437(8) Uani 1 1 d .
H2B H -0.1768 0.7524 0.1508 0.052 Uiso 1 1 calc R
O2 O 0.2615(4) 0.4651(4) 0.3212(3) 0.0891(10) Uani 1 1 d .
O3 O -0.2681(3) 0.7850(3) 0.3228(2) 0.0525(6) Uani 1 1 d .
C3 C -0.0274(4) 0.9853(4) 0.2624(3) 0.0381(7) Uani 1 1 d .
N3 N -0.2825(4) 1.0749(4) 0.1387(3) 0.0578(8) Uani 1 1 d .
N4 N -0.1159(4) 1.2648(4) 0.3425(3) 0.0631(9) Uani 1 1 d .
C4 C 0.2415(4) 0.5158(4) 0.2156(4) 0.0595(10) Uani 1 1 d .
O4 O -0.3787(5) 0.6492(5) 0.2021(3) 0.1016(13) Uani 1 1 d .
O5 O -0.2671(3) 1.2077(3) 0.1217(3) 0.0747(9) Uani 1 1 d .
N5 N 0.1680(4) 1.1111(3) 0.3367(3) 0.0551(8) Uani 1 1 d .
C5 C 0.3403(5) 0.4567(5) 0.1066(5) 0.0812(14) Uani 1 1 d .
H5A H 0.4302 0.3657 0.1324 0.122 Uiso 1 1 calc R
H5B H 0.3793 0.5397 0.0695 0.122 Uiso 1 1 calc R
H5C H 0.2758 0.4258 0.0465 0.122 Uiso 1 1 calc R
N6 N 0.0284(4) 1.2125(4) 0.1372(3) 0.0564(8) Uani 1 1 d .
O6 O -0.3890(3) 1.0280(4) 0.1006(3) 0.0808(9) Uani 1 1 d .
C6 C -0.3761(5) 0.7060(5) 0.2985(4) 0.0579(9) Uani 1 1 d .
O7 O -0.2287(4) 1.2253(4) 0.3808(3) 0.0960(11) Uani 1 1 d .
C7 C -0.4819(5) 0.7065(6) 0.4068(4) 0.0805(13) Uani 1 1 d .
H7A H -0.5573 0.6506 0.3885 0.121 Uiso 1 1 calc R
H7B H -0.5398 0.8150 0.4240 0.121 Uiso 1 1 calc R
H7C H -0.4175 0.6543 0.4784 0.121 Uiso 1 1 calc R
C8 C 0.0054(4) 1.1434(4) 0.2676(3) 0.0443(8) Uani 1 1 d .
O8 O -0.0854(5) 1.3850(4) 0.3616(4) 0.1043(13) Uani 1 1 d .
O9 O 0.1608(4) 1.0996(4) 0.4484(3) 0.0877(10) Uani 1 1 d .
O10 O 0.2843(4) 1.0969(4) 0.2736(3) 0.0820(9) Uani 1 1 d .
O11 O 0.0048(4) 1.3544(4) 0.1210(3) 0.0835(10) Uani 1 1 d .
O12 O 0.0759(4) 1.1111(4) 0.0626(3) 0.0755(9) Uani 1 1 d .
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 O1 C1 116.1(3)
N3 N1 C3 127.5(3)
N3 N1 C2 123.1(3)
C3 N1 C2 109.0(3)
O1 C1 N2 106.9(3)
O1 C1 C2 108.3(3)
N2 C1 C2 107.0(3)
O1 C1 H1A 111.5
N2 C1 H1A 111.5
C2 C1 H1A 111.5
C3 N2 C1 107.2(3)
O3 C2 N1 108.5(3)
O3 C2 C1 109.8(3)
N1 C2 C1 100.2(2)
O3 C2 H2B 112.6
N1 C2 H2B 112.6
C1 C2 H2B 112.6
C6 O3 C2 118.1(3)
N2 C3 N1 115.1(3)
N2 C3 C8 120.0(3)
N1 C3 C8 124.9(3)
O6 N3 O5 127.8(3)
O6 N3 N1 115.6(3)
O5 N3 N1 116.6(3)
O8 N4 O7 127.3(4)
O8 N4 C8 116.9(3)
O7 N4 C8 115.7(3)
O2 C4 O1 121.3(4)
O2 C4 C5 128.6(4)
O1 C4 C5 110.1(4)
O10 N5 O9 128.3(4)
O10 N5 C8 116.8(3)
O9 N5 C8 114.9(3)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
O11 N6 O12 128.0(3)
O11 N6 C8 119.0(3)
O12 N6 C8 113.0(3)
O4 C6 O3 121.7(4)
O4 C6 C7 128.0(4)
O3 C6 C7 110.3(3)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C3 C8 N4 114.4(3)
C3 C8 N6 111.5(3)
N4 C8 N6 111.9(3)
C3 C8 N5 107.3(2)
N4 C8 N5 105.2(3)
N6 C8 N5 105.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.374(4)
O1 C1 1.417(4)
N1 N3 1.370(4)
N1 C3 1.396(4)
N1 C2 1.447(4)
C1 N2 1.467(4)
C1 C2 1.535(5)
C1 H1A 0.9800
N2 C3 1.254(4)
C2 O3 1.411(4)
C2 H2B 0.9800
O2 C4 1.186(5)
O3 C6 1.363(4)
C3 C8 1.506(4)
N3 O6 1.206(4)
N3 O5 1.218(4)
N4 O8 1.195(4)
N4 O7 1.198(4)
N4 C8 1.515(4)
C4 C5 1.469(6)
O4 C6 1.177(5)
N5 O10 1.191(4)
N5 O9 1.199(4)
N5 C8 1.541(5)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
N6 O11 1.202(4)
N6 O12 1.208(4)
N6 C8 1.528(4)
C6 C7 1.475(6)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
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
C4 O1 C1 N2 95.6(3)
C4 O1 C1 C2 -149.4(3)
O1 C1 N2 C3 105.6(3)
C2 C1 N2 C3 -10.2(3)
N3 N1 C2 O3 -81.1(4)
C3 N1 C2 O3 105.7(3)
N3 N1 C2 C1 163.9(3)
C3 N1 C2 C1 -9.3(3)
O1 C1 C2 O3 142.7(2)
N2 C1 C2 O3 -102.4(3)
O1 C1 C2 N1 -103.3(3)
N2 C1 C2 N1 11.6(3)
N1 C2 O3 C6 128.7(3)
C1 C2 O3 C6 -122.7(3)
C1 N2 C3 N1 4.3(4)
C1 N2 C3 C8 -175.1(3)
N3 N1 C3 N2 -169.1(3)
C2 N1 C3 N2 3.8(4)
N3 N1 C3 C8 10.3(5)
C2 N1 C3 C8 -176.8(3)
C3 N1 N3 O6 178.2(3)
C2 N1 N3 O6 6.2(5)
C3 N1 N3 O5 -1.9(5)
C2 N1 N3 O5 -173.9(3)
C1 O1 C4 O2 6.2(5)
C1 O1 C4 C5 -174.0(3)
C2 O3 C6 O4 0.3(6)
C2 O3 C6 C7 -179.2(3)
N2 C3 C8 N4 -118.5(3)
N1 C3 C8 N4 62.1(4)
N2 C3 C8 N6 113.2(3)
N1 C3 C8 N6 -66.1(4)
N2 C3 C8 N5 -2.3(4)
N1 C3 C8 N5 178.4(3)
O8 N4 C8 C3 171.7(4)
O7 N4 C8 C3 -5.1(5)
O8 N4 C8 N6 -60.3(4)
O7 N4 C8 N6 123.0(4)
O8 N4 C8 N5 54.2(4)
O7 N4 C8 N5 -122.5(4)
O11 N6 C8 C3 156.7(3)
O12 N6 C8 C3 -26.0(4)
O11 N6 C8 N4 27.1(4)
O12 N6 C8 N4 -155.6(3)
O11 N6 C8 N5 -86.9(4)
O12 N6 C8 N5 90.4(3)
O10 N5 C8 C3 97.5(3)
O9 N5 C8 C3 -80.8(3)
O10 N5 C8 N4 -140.4(3)
O9 N5 C8 N4 41.4(4)
O10 N5 C8 N6 -21.7(4)
O9 N5 C8 N6 160.0(3)
