#------------------------------------------------------------------------------
#$Date: 2023-08-05 12:36:32 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285532 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/69/7246997.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_7246997
loop_
_publ_author_name
'Zhang, Wenjin'
'Yang, Yiling'
'Shi, Shaoyi'
'Pang, Siping'
'Li, Yuchuan'
'Sun, Chenghui'
_publ_section_title
;
 Regulation of stability and density of energetic materials via
 isomerism.
;
_journal_issue                   30
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              20168
_journal_page_last               20172
_journal_paper_doi               10.1039/d3cp02039h
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C3 H2 N6 O6'
_chemical_formula_weight         218.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-12-06 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.970(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5399(11)
_cell_length_b                   8.8744(11)
_cell_length_c                   10.5124(14)
_cell_measurement_reflns_used    8949
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      3.32
_cell_volume                     793.20(17)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1732
_diffrn_reflns_point_group_measured_fraction_full 0.617
_diffrn_reflns_point_group_measured_fraction_max 0.594
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.939
_diffrn_reflns_theta_min         3.318
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1140
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0382P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.240
_reflns_Friedel_fraction_full    0.237
_reflns_Friedel_fraction_max     0.231
_reflns_number_gt                987
_reflns_number_total             1140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp02039h2.cif
_cod_data_source_block           3_a
_cod_depositor_comments
'Adding full bibliography for 7246997--7247000.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7246997
_shelx_shelxl_version_number     2014/7
_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   0.962
_shelx_estimated_absorpt_t_max   0.969
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'
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
C1 C 0.6672(3) 0.5493(2) 0.6391(2) 0.0325(5) Uani 1 1 d . . . . .
C2 C 0.6314(3) 0.4714(3) 0.7355(3) 0.0430(6) Uani 1 1 d . . . . .
H2 H 0.7030 0.4388 0.8260 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2677(3) 0.5383(2) 0.4580(2) 0.0336(5) Uani 1 1 d . . . . .
H3 H 0.2081 0.4652 0.4841 0.040 Uiso 1 1 calc R U . . .
N1 N 0.8217(3) 0.5977(2) 0.6602(3) 0.0420(5) Uani 1 1 d . . . . .
N2 N 0.5409(2) 0.5799(2) 0.5206(2) 0.0343(4) Uani 1 1 d . . . . .
N3 N 0.4295(2) 0.51721(19) 0.5473(2) 0.0329(4) Uani 1 1 d . . . . .
N4 N 0.4781(2) 0.4521(2) 0.6756(2) 0.0399(5) Uani 1 1 d . . . . .
N5 N 0.2145(3) 0.6972(2) 0.4718(3) 0.0452(5) Uani 1 1 d . . . . .
N6 N 0.2322(2) 0.5129(2) 0.3035(2) 0.0360(4) Uani 1 1 d . . . . .
O1 O 0.8358(2) 0.6483(2) 0.5599(2) 0.0602(5) Uani 1 1 d . . . . .
O2 O 0.9273(2) 0.5837(3) 0.7809(2) 0.0668(6) Uani 1 1 d . . . . .
O3 O 0.3144(2) 0.79130(19) 0.5289(3) 0.0668(6) Uani 1 1 d . . . . .
O4 O 0.0757(2) 0.7136(2) 0.4275(3) 0.0737(7) Uani 1 1 d . . . . .
O5 O 0.1797(2) 0.6163(2) 0.2203(2) 0.0540(5) Uani 1 1 d . . . . .
O6 O 0.2596(2) 0.38698(19) 0.2779(2) 0.0499(5) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 111.9(2) . . ?
N2 C1 N1 121.0(2) . . ?
C2 C1 N1 127.1(2) . . ?
N4 C2 C1 107.6(2) . . ?
N3 C3 N6 109.78(17) . . ?
N3 C3 N5 111.72(18) . . ?
N6 C3 N5 108.40(18) . . ?
O1 N1 O2 125.5(2) . . ?
O1 N1 C1 118.9(2) . . ?
O2 N1 C1 115.6(2) . . ?
C1 N2 N3 100.89(18) . . ?
N2 N3 N4 116.44(18) . . ?
N2 N3 C3 122.65(18) . . ?
N4 N3 C3 120.10(18) . . ?
C2 N4 N3 103.16(18) . . ?
O4 N5 O3 126.6(2) . . ?
O4 N5 C3 115.6(2) . . ?
O3 N5 C3 117.77(19) . . ?
O6 N6 O5 127.1(2) . . ?
O6 N6 C3 114.24(19) . . ?
O5 N6 C3 118.69(19) . . ?
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
C1 N2 1.310(3) . ?
C1 C2 1.391(4) . ?
C1 N1 1.453(3) . ?
C2 N4 1.315(3) . ?
C3 N3 1.409(3) . ?
C3 N6 1.518(3) . ?
C3 N5 1.528(3) . ?
N1 O1 1.208(3) . ?
N1 O2 1.216(3) . ?
N2 N3 1.338(3) . ?
N3 N4 1.342(3) . ?
N5 O4 1.197(3) . ?
N5 O3 1.203(3) . ?
N6 O6 1.206(3) . ?
N6 O5 1.209(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
N2 C1 C2 N4 0.1(3) . . . . ?
N1 C1 C2 N4 178.89(19) . . . . ?
N2 C1 N1 O1 -10.2(3) . . . . ?
C2 C1 N1 O1 171.1(2) . . . . ?
N2 C1 N1 O2 169.4(2) . . . . ?
C2 C1 N1 O2 -9.2(3) . . . . ?
C2 C1 N2 N3 -0.7(2) . . . . ?
N1 C1 N2 N3 -179.56(18) . . . . ?
C1 N2 N3 N4 1.1(2) . . . . ?
C1 N2 N3 C3 170.86(19) . . . . ?
N6 C3 N3 N2 47.7(2) . . . . ?
N5 C3 N3 N2 -72.6(3) . . . . ?
N6 C3 N3 N4 -142.9(2) . . . . ?
N5 C3 N3 N4 96.8(2) . . . . ?
C1 C2 N4 N3 0.5(2) . . . . ?
N2 N3 N4 C2 -1.1(2) . . . . ?
C3 N3 N4 C2 -171.08(19) . . . . ?
N3 C3 N5 O4 -162.8(2) . . . . ?
N6 C3 N5 O4 76.1(3) . . . . ?
N3 C3 N5 O3 15.1(3) . . . . ?
N6 C3 N5 O3 -106.0(3) . . . . ?
N3 C3 N6 O6 62.5(2) . . . . ?
N5 C3 N6 O6 -175.24(18) . . . . ?
N3 C3 N6 O5 -118.2(2) . . . . ?
N5 C3 N6 O5 4.1(3) . . . . ?
