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#$Date: 2021-07-05 20:27:15 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267139 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/73/7707318.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_7707318
loop_
_publ_author_name
'Yang, Kaidi'
'Bi, Fuqiang'
'Xue, Qi'
'Huo, Huan'
'Bai, Chao'
'Zhang, Junlin'
'Wang, Bozhou'
_publ_section_title
;
 Synthesis and properties of azamonocyclic energetic materials with
 geminal explosophores.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8338
_journal_page_last               8348
_journal_paper_doi               10.1039/d1dt00581b
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C4 H6 N8 O6'
_chemical_formula_sum            'C4 H6 N8 O6'
_chemical_formula_weight         262.17
_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-2018/3
_audit_update_record
;
2021-04-22 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.220(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3083(10)
_cell_length_b                   6.3183(4)
_cell_length_c                   12.2565(8)
_cell_measurement_reflns_used    1945
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      3.24
_cell_volume                     973.15(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5950
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         3.242
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0280
_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)+(0.0232P)²+0.0310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0600
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1533
_reflns_number_total             1716
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00581b2.cif
_cod_data_source_block           w2
_cod_depositor_comments
'Adding full bibliography for 7707318--7707319.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7707318
_shelx_shelxl_version_number     2018/3
_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   0.976
_shelx_estimated_absorpt_t_max   0.980
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 0.3665(2) 0.4180(5) 0.3238(3) 0.0336(7) Uani 1 1 d . . . . .
H1A H 0.339600 0.292126 0.274694 0.040 Uiso 1 1 calc R U . . .
H1B H 0.333522 0.545045 0.278961 0.040 Uiso 1 1 calc R U . . .
C2 C 0.5420(2) 0.2684(5) 0.4323(3) 0.0337(7) Uani 1 1 d . . . . .
H2A H 0.618952 0.300261 0.454738 0.040 Uiso 1 1 calc R U . . .
H2B H 0.529338 0.128655 0.393649 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5081(2) 0.2613(5) 0.5410(3) 0.0306(7) Uani 1 1 d . . . . .
C4 C 0.3872(3) 0.2385(5) 0.5093(3) 0.0341(7) Uani 1 1 d . . . . .
H4A H 0.364437 0.097735 0.474553 0.041 Uiso 1 1 calc R U . . .
H4B H 0.366584 0.251240 0.579641 0.041 Uiso 1 1 calc R U . . .
N1 N 0.4816(2) 0.4301(4) 0.3528(2) 0.0325(6) Uani 1 1 d . . . . .
N2 N 0.3358(2) 0.4041(4) 0.4273(2) 0.0326(6) Uani 1 1 d . . . . .
N3 N 0.5258(2) 0.6303(4) 0.3582(2) 0.0358(7) Uani 1 1 d . . . . .
N4 N 0.3031(2) 0.5858(5) 0.4679(2) 0.0365(6) Uani 1 1 d . . . . .
N5 N 0.5391(2) 0.4443(4) 0.6152(2) 0.0340(6) Uani 1 1 d . . . . .
N6 N 0.6354(2) 0.4960(4) 0.6407(2) 0.0367(6) Uani 1 1 d . . . . .
N7 N 0.7182(3) 0.5600(5) 0.6705(3) 0.0458(8) Uani 1 1 d . . . . .
N8 N 0.5583(2) 0.0596(4) 0.6079(2) 0.0368(7) Uani 1 1 d . . . . .
O1 O 0.62181(19) 0.6472(4) 0.4081(2) 0.0440(6) Uani 1 1 d . . . . .
O2 O 0.46732(18) 0.7730(3) 0.30622(19) 0.0393(6) Uani 1 1 d . . . . .
O3 O 0.28220(19) 0.7392(4) 0.4041(2) 0.0418(6) Uani 1 1 d . . . . .
O4 O 0.2914(2) 0.5767(4) 0.5631(2) 0.0478(7) Uani 1 1 d . . . . .
O5 O 0.5181(2) -0.1080(4) 0.5678(2) 0.0615(8) Uani 1 1 d . . . . .
O6 O 0.63514(19) 0.0782(4) 0.6944(2) 0.0437(6) 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
N1 C1 N2 111.3(2) . . ?
N1 C1 H1A 109.4 . . ?
N2 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N1 C2 C3 110.2(2) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N5 C3 C4 107.0(3) . . ?
N5 C3 C2 114.6(2) . . ?
C4 C3 C2 111.4(2) . . ?
N5 C3 N8 110.1(2) . . ?
C4 C3 N8 107.0(2) . . ?
C2 C3 N8 106.5(2) . . ?
N2 C4 C3 108.9(3) . . ?
N2 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N3 N1 C1 117.1(2) . . ?
N3 N1 C2 118.4(2) . . ?
C1 N1 C2 115.5(2) . . ?
N4 N2 C4 118.8(3) . . ?
N4 N2 C1 118.5(2) . . ?
C4 N2 C1 116.2(3) . . ?
O2 N3 O1 125.2(3) . . ?
O2 N3 N1 117.3(3) . . ?
O1 N3 N1 117.3(3) . . ?
O3 N4 O4 125.0(3) . . ?
O3 N4 N2 117.6(3) . . ?
O4 N4 N2 117.3(3) . . ?
N6 N5 C3 114.9(3) . . ?
N7 N6 N5 172.0(3) . . ?
O6 N8 O5 124.8(3) . . ?
O6 N8 C3 118.5(3) . . ?
O5 N8 C3 116.7(3) . . ?
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 N1 1.456(4) . ?
C1 N2 1.459(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.457(4) . ?
C2 C3 1.541(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N5 1.444(4) . ?
C3 C4 1.533(4) . ?
C3 N8 1.543(4) . ?
C4 N2 1.456(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N1 N3 1.388(4) . ?
N2 N4 1.378(4) . ?
N3 O2 1.224(3) . ?
N3 O1 1.226(3) . ?
N4 O3 1.219(3) . ?
N4 O4 1.228(3) . ?
N5 N6 1.258(4) . ?
N6 N7 1.116(4) . ?
N8 O6 1.212(3) . ?
N8 O5 1.215(4) . ?
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 C3 N5 -69.2(3) . . . . ?
N1 C2 C3 C4 52.6(3) . . . . ?
N1 C2 C3 N8 168.9(2) . . . . ?
N5 C3 C4 N2 73.1(3) . . . . ?
C2 C3 C4 N2 -52.9(3) . . . . ?
N8 C3 C4 N2 -169.0(3) . . . . ?
N2 C1 N1 N3 -95.8(3) . . . . ?
N2 C1 N1 C2 50.9(3) . . . . ?
C3 C2 N1 N3 94.3(3) . . . . ?
C3 C2 N1 C1 -52.0(3) . . . . ?
C3 C4 N2 N4 -97.3(3) . . . . ?
C3 C4 N2 C1 54.0(3) . . . . ?
N1 C1 N2 N4 98.9(3) . . . . ?
N1 C1 N2 C4 -52.5(3) . . . . ?
C1 N1 N3 O2 -21.5(4) . . . . ?
C2 N1 N3 O2 -167.3(3) . . . . ?
C1 N1 N3 O1 163.1(3) . . . . ?
C2 N1 N3 O1 17.4(4) . . . . ?
C4 N2 N4 O3 164.2(3) . . . . ?
C1 N2 N4 O3 13.6(4) . . . . ?
C4 N2 N4 O4 -19.9(4) . . . . ?
C1 N2 N4 O4 -170.5(3) . . . . ?
C4 C3 N5 N6 -173.9(2) . . . . ?
C2 C3 N5 N6 -49.9(3) . . . . ?
N8 C3 N5 N6 70.1(3) . . . . ?
N5 C3 N8 O6 -20.0(4) . . . . ?
C4 C3 N8 O6 -135.9(3) . . . . ?
C2 C3 N8 O6 104.9(3) . . . . ?
N5 C3 N8 O5 161.2(3) . . . . ?
C4 C3 N8 O5 45.3(4) . . . . ?
C2 C3 N8 O5 -74.0(3) . . . . ?
