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#$Date: 2022-08-17 01:46:25 +0300 (Wed, 17 Aug 2022) $
#$Revision: 277264 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/09/7710983.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_7710983
loop_
_publ_author_name
'Zhilin, Egor'
'Ananyev, Ivan V.'
'Pivkina, Alla N.'
'Fershtat, Leonid'
_publ_section_title
;
 Renaissance of Dinitroazetidine: Novel Hybrid Energetic Boosters and
 Oxidizers
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02445D
_journal_year                    2022
_chemical_formula_moiety         'C6 H4 N6 O9'
_chemical_formula_sum            'C6 H4 N6 O9'
_chemical_formula_weight         304.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2022-06-17 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.986(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.7181(13)
_cell_length_b                   5.4680(2)
_cell_length_c                   11.2106(4)
_cell_measurement_reflns_used    242
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     2186.53(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36666
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.128
_diffrn_reflns_theta_min         2.284
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0436P)²+1.0637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2610
_reflns_number_total             3208
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d2dt02445d2.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7710983
_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.
;
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
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'
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
O4 O 0.25691(2) 0.16420(16) 0.15383(8) 0.01583(19) Uani 1 1 d . . . . .
O3 O 0.30236(3) 0.16823(15) 0.03108(8) 0.01558(19) Uani 1 1 d . . . . .
O2 O 0.28222(2) 0.66984(16) 0.10984(8) 0.01486(19) Uani 1 1 d . . . . .
O1 O 0.32168(3) 0.76007(15) 0.25804(8) 0.01588(19) Uani 1 1 d . . . . .
N1 N 0.35060(3) 0.23167(18) 0.35084(9) 0.0115(2) Uani 1 1 d . . . . .
C3 C 0.31006(3) 0.2835(2) 0.34811(10) 0.0107(2) Uani 1 1 d . . . . .
O5 O 0.36559(3) 0.28283(18) 0.54785(8) 0.0186(2) Uani 1 1 d . . . . .
N3 N 0.28866(3) 0.21364(17) 0.12595(9) 0.0109(2) Uani 1 1 d . . . . .
O6 O 0.47013(3) 0.0736(2) 0.36728(10) 0.0274(2) Uani 1 1 d . . . . .
O7 O 0.41602(3) -0.07815(19) 0.27348(9) 0.0275(2) Uani 1 1 d . . . . .
N2 N 0.30473(3) 0.61768(17) 0.19112(9) 0.0109(2) Uani 1 1 d . . . . .
O8 O 0.42522(3) 0.6876(2) 0.55254(11) 0.0311(3) Uani 1 1 d . . . . .
N4 N 0.42888(3) 0.0650(2) 0.34660(10) 0.0206(2) Uani 1 1 d . . . . .
N5 N 0.47824(3) 0.2376(2) 0.45648(12) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.31284(3) 0.35109(19) 0.21580(10) 0.0091(2) Uani 1 1 d . . . . .
C1 C 0.35467(3) 0.2843(2) 0.22271(11) 0.0120(2) Uani 1 1 d . . . . .
O9 O 0.46372(4) 0.4806(2) 0.67105(10) 0.0382(3) Uani 1 1 d . . . . .
N6 N 0.44507(3) 0.5117(2) 0.57859(11) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.37449(3) 0.2514(2) 0.44542(11) 0.0126(2) Uani 1 1 d . . . . .
C5 C 0.41500(4) 0.2248(2) 0.42199(12) 0.0164(2) Uani 1 1 d . . . . .
C6 C 0.44633(4) 0.3215(3) 0.48730(12) 0.0195(3) Uani 1 1 d . . . . .
H3B H 0.3037(4) 0.414(3) 0.3980(13) 0.012(3) Uiso 1 1 d . . . . .
H1B H 0.3600(4) 0.143(3) 0.1753(14) 0.014(4) Uiso 1 1 d . . . . .
H3A H 0.2944(4) 0.141(3) 0.3615(13) 0.011(3) Uiso 1 1 d . . . . .
H1A H 0.3697(4) 0.417(3) 0.2077(13) 0.013(4) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C3 126.12(10) . . ?
C4 N1 C1 131.80(10) . . ?
C3 N1 C1 95.09(9) . . ?
N1 C3 C2 87.34(8) . . ?
N1 C3 H3B 113.7(9) . . ?
C2 C3 H3B 114.9(9) . . ?
N1 C3 H3A 114.4(9) . . ?
C2 C3 H3A 114.0(9) . . ?
H3B C3 H3A 110.8(12) . . ?
O3 N3 O4 126.73(10) . . ?
O3 N3 C2 116.49(10) . . ?
O4 N3 C2 116.75(9) . . ?
N5 O6 N4 107.90(9) . . ?
O2 N2 O1 126.73(10) . . ?
O2 N2 C2 118.46(9) . . ?
O1 N2 C2 114.80(9) . . ?
O7 N4 C5 135.79(12) . . ?
O7 N4 O6 117.88(10) . . ?
C5 N4 O6 106.30(11) . . ?
C6 N5 O6 105.86(11) . . ?
N3 C2 N2 105.27(9) . . ?
N3 C2 C1 116.16(9) . . ?
N2 C2 C1 114.57(9) . . ?
N3 C2 C3 117.73(9) . . ?
N2 C2 C3 112.82(9) . . ?
C1 C2 C3 90.32(9) . . ?
N1 C1 C2 87.17(8) . . ?
N1 C1 H1B 114.4(9) . . ?
C2 C1 H1B 112.5(9) . . ?
N1 C1 H1A 114.7(9) . . ?
C2 C1 H1A 112.1(9) . . ?
H1B C1 H1A 113.4(13) . . ?
O9 N6 O8 126.87(14) . . ?
O9 N6 C6 117.55(13) . . ?
O8 N6 C6 115.57(12) . . ?
O5 C4 N1 125.05(11) . . ?
O5 C4 C5 118.84(11) . . ?
N1 C4 C5 116.08(11) . . ?
N4 C5 C6 105.36(11) . . ?
N4 C5 C4 124.99(12) . . ?
C6 C5 C4 128.61(12) . . ?
N5 C6 C5 114.56(13) . . ?
N5 C6 N6 119.99(12) . . ?
C5 C6 N6 125.35(12) . . ?
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
O4 N3 1.2221(13) . ?
O3 N3 1.2193(13) . ?
O2 N2 1.2171(13) . ?
O1 N2 1.2199(13) . ?
N1 C4 1.3303(16) . ?
N1 C3 1.4740(15) . ?
N1 C1 1.4796(15) . ?
C3 C2 1.5369(16) . ?
C3 H3B 0.943(15) . ?
C3 H3A 0.977(15) . ?
O5 C4 1.2194(15) . ?
N3 C2 1.4949(15) . ?
O6 N5 1.3631(17) . ?
O6 N4 1.4804(15) . ?
O7 N4 1.2068(16) . ?
N2 C2 1.5090(14) . ?
O8 N6 1.2211(17) . ?
N4 C5 1.3295(17) . ?
N5 C6 1.2922(18) . ?
C2 C1 1.5362(16) . ?
C1 H1B 0.961(15) . ?
C1 H1A 0.923(15) . ?
O9 N6 1.2145(16) . ?
N6 C6 1.4612(19) . ?
C4 C5 1.4913(17) . ?
C5 C6 1.4081(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
C4 N1 C3 C2 151.05(11) . . . . ?
C1 N1 C3 C2 -2.24(9) . . . . ?
N5 O6 N4 O7 -177.14(12) . . . . ?
N5 O6 N4 C5 1.02(14) . . . . ?
N4 O6 N5 C6 -0.24(14) . . . . ?
O3 N3 C2 N2 90.09(11) . . . . ?
O4 N3 C2 N2 -88.01(11) . . . . ?
O3 N3 C2 C1 -37.82(14) . . . . ?
O4 N3 C2 C1 144.08(10) . . . . ?
O3 N3 C2 C3 -143.20(10) . . . . ?
O4 N3 C2 C3 38.70(14) . . . . ?
O2 N2 C2 N3 -0.33(13) . . . . ?
O1 N2 C2 N3 178.77(9) . . . . ?
O2 N2 C2 C1 128.53(11) . . . . ?
O1 N2 C2 C1 -52.38(13) . . . . ?
O2 N2 C2 C3 -129.99(10) . . . . ?
O1 N2 C2 C3 49.11(13) . . . . ?
N1 C3 C2 N3 122.22(10) . . . . ?
N1 C3 C2 N2 -114.82(9) . . . . ?
N1 C3 C2 C1 2.15(8) . . . . ?
C4 N1 C1 C2 -148.61(12) . . . . ?
C3 N1 C1 C2 2.24(9) . . . . ?
N3 C2 C1 N1 -123.55(9) . . . . ?
N2 C2 C1 N1 113.27(10) . . . . ?
C3 C2 C1 N1 -2.14(8) . . . . ?
C3 N1 C4 O5 10.72(19) . . . . ?
C1 N1 C4 O5 153.82(12) . . . . ?
C3 N1 C4 C5 -171.22(10) . . . . ?
C1 N1 C4 C5 -28.12(17) . . . . ?
O7 N4 C5 C6 176.37(15) . . . . ?
O6 N4 C5 C6 -1.30(14) . . . . ?
O7 N4 C5 C4 7.2(2) . . . . ?
O6 N4 C5 C4 -170.48(11) . . . . ?
O5 C4 C5 N4 138.64(13) . . . . ?
N1 C4 C5 N4 -39.55(18) . . . . ?
O5 C4 C5 C6 -28.0(2) . . . . ?
N1 C4 C5 C6 153.85(13) . . . . ?
O6 N5 C6 C5 -0.62(16) . . . . ?
O6 N5 C6 N6 -177.33(11) . . . . ?
N4 C5 C6 N5 1.29(17) . . . . ?
C4 C5 C6 N5 169.94(12) . . . . ?
N4 C5 C6 N6 177.79(12) . . . . ?
C4 C5 C6 N6 -13.6(2) . . . . ?
O9 N6 C6 N5 -48.90(18) . . . . ?
O8 N6 C6 N5 130.65(14) . . . . ?
O9 N6 C6 C5 134.77(14) . . . . ?
O8 N6 C6 C5 -45.67(19) . . . . ?
