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#$Date: 2022-05-05 23:46:23 +0300 (Thu, 05 May 2022) $
#$Revision: 275027 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/13/7061377.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_7061377
loop_
_publ_author_name
'Wang, Qian'
'Lu, Ming'
_publ_section_title
;
 Carbon skeleton: route to investigate high-performance insensitive
 energetic materials
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6690
_journal_page_last               6693
_journal_paper_doi               10.1039/D1NJ05168G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C5 H2 N3 O6, H4 N O'
_chemical_formula_sum            'C5 H6 N4 O7'
_chemical_formula_weight         234.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-08-04 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.364(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2036(5)
_cell_length_b                   7.0213(5)
_cell_length_c                   8.3381(5)
_cell_measurement_reflns_used    2939
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.92
_cell_volume                     408.55(5)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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  0.0167
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4088
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.402
_diffrn_reflns_theta_min         2.919
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 678 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0300
_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)+(0.0538P)²+0.0176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                1652
_reflns_number_total             1794
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05168g3.cif
_cod_data_source_block           Wq190425_1_a
_cod_depositor_comments
'Adding full bibliography for 7061376--7061378.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7061377
_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   0.965
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_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 0.7660(2) 0.3616(3) 0.4480(2) 0.0188(5) Uani 1 1 d . . . . .
C2 C 0.7161(3) 0.4803(3) 0.5712(2) 0.0206(5) Uani 1 1 d . . . . .
C3 C 0.7338(3) 0.6763(3) 0.5321(2) 0.0196(4) Uani 1 1 d . . . . .
C4 C 0.7964(3) 0.6774(3) 0.3662(2) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.8169(3) 0.4819(3) 0.3272(3) 0.0210(4) Uani 1 1 d . . . . .
N1 N 0.7667(2) 0.1769(3) 0.4478(2) 0.0267(4) Uani 1 1 d . . . . .
H1A H 0.800064 0.115966 0.369931 0.032 Uiso 1 1 calc R U . . .
H1B H 0.733896 0.115316 0.525594 0.032 Uiso 1 1 calc R U . . .
N2 N 0.6546(3) 0.4133(3) 0.7033(2) 0.0239(4) Uani 1 1 d . . . . .
N3 N 0.8785(2) 0.4169(3) 0.1927(2) 0.0251(4) Uani 1 1 d . . . . .
O1 O 0.7110(2) 0.8226(2) 0.60477(18) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.8202(2) 0.8234(3) 0.29533(17) 0.0284(4) Uani 1 1 d . . . . .
O3 O 0.6435(3) 0.2373(2) 0.7258(2) 0.0338(4) Uani 1 1 d . . . . .
O4 O 0.6039(3) 0.5297(2) 0.79750(19) 0.0334(4) Uani 1 1 d . . . . .
O5 O 0.9260(3) 0.5340(3) 0.0991(2) 0.0373(4) Uani 1 1 d . . . . .
O6 O 0.8891(3) 0.2417(2) 0.1703(3) 0.0364(5) Uani 1 1 d . . . . .
N4 N 0.2767(2) 0.3964(3) 0.04832(19) 0.0279(4) Uani 1 1 d . . . . .
H4B H 0.260962 0.346036 0.142026 0.042 Uiso 1 1 calc R U . . .
H4A H 0.201283 0.336408 -0.037562 0.042 Uiso 1 1 calc R U . . .
H4C H 0.246017 0.519391 0.044399 0.042 Uiso 1 1 calc R U . . .
O7 O 0.4682(2) 0.3765(4) 0.0422(2) 0.0482(6) Uani 1 1 d . . . . .
H7 H 0.474(5) 0.436(6) -0.074(4) 0.072 Uiso 1 1 d . U . . .
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 C5 126.05(18) . . ?
N1 C1 C2 125.65(19) . . ?
C5 C1 C2 108.30(19) . . ?
N2 C2 C3 125.5(2) . . ?
N2 C2 C1 124.39(19) . . ?
C3 C2 C1 110.11(18) . . ?
O1 C3 C2 131.73(18) . . ?
O1 C3 C4 122.63(19) . . ?
C2 C3 C4 105.64(17) . . ?
O2 C4 C5 131.68(18) . . ?
O2 C4 C3 122.85(18) . . ?
C5 C4 C3 105.47(17) . . ?
N3 C5 C4 125.1(2) . . ?
N3 C5 C1 124.47(19) . . ?
C4 C5 C1 110.43(18) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O4 N2 O3 120.7(2) . . ?
O4 N2 C2 119.0(2) . . ?
O3 N2 C2 120.3(2) . . ?
O5 N3 O6 121.5(2) . . ?
O5 N3 C5 119.1(2) . . ?
O6 N3 C5 119.4(2) . . ?
O7 N4 H4B 109.5 . . ?
O7 N4 H4A 109.5 . . ?
H4B N4 H4A 109.5 . . ?
O7 N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
N4 O7 H7 104.6(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 N1 1.297(3) . ?
C1 C5 1.430(3) . ?
C1 C2 1.436(3) . ?
C2 N2 1.369(3) . ?
C2 C3 1.427(3) . ?
C3 O1 1.224(3) . ?
C3 C4 1.558(3) . ?
C4 O2 1.216(3) . ?
C4 C5 1.427(3) . ?
C5 N3 1.382(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 O4 1.249(3) . ?
N2 O3 1.256(3) . ?
N3 O5 1.239(3) . ?
N3 O6 1.250(3) . ?
N4 O7 1.401(2) . ?
N4 H4B 0.8900 . ?
N4 H4A 0.8900 . ?
N4 H4C 0.8900 . ?
O7 H7 1.06(4) . ?
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
_geom_hbond_publ_flag
O7 H7 O4 1.06(4) 1.72(4) 2.695(2) 150(3) 1_554 yes
O7 H7 N2 1.06(4) 2.53(3) 3.425(3) 142(3) 1_554 yes
N4 H4C O6 0.89 2.39 3.090(3) 135.4 2_655 yes
N4 H4C O3 0.89 2.43 3.012(3) 123.6 2_656 yes
N4 H4A O5 0.89 2.32 3.038(3) 137.7 2_645 yes
N4 H4A O2 0.89 2.12 2.823(2) 135.5 2_645 yes
N4 H4B O4 0.89 2.43 2.911(3) 114.5 2_646 yes
N4 H4B O1 0.89 2.08 2.918(2) 157.3 2_646 yes
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 C1 C2 N2 -2.7(3) . . . . ?
C5 C1 C2 N2 178.05(18) . . . . ?
N1 C1 C2 C3 179.29(17) . . . . ?
C5 C1 C2 C3 0.0(2) . . . . ?
N2 C2 C3 O1 4.3(3) . . . . ?
C1 C2 C3 O1 -177.7(2) . . . . ?
N2 C2 C3 C4 -176.61(18) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
O1 C3 C4 O2 -2.6(3) . . . . ?
C2 C3 C4 O2 178.20(18) . . . . ?
O1 C3 C4 C5 176.93(18) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
O2 C4 C5 N3 2.2(4) . . . . ?
C3 C4 C5 N3 -177.22(19) . . . . ?
O2 C4 C5 C1 -178.2(2) . . . . ?
C3 C4 C5 C1 2.4(2) . . . . ?
N1 C1 C5 N3 -1.3(3) . . . . ?
C2 C1 C5 N3 178.01(18) . . . . ?
N1 C1 C5 C4 179.14(17) . . . . ?
C2 C1 C5 C4 -1.6(2) . . . . ?
C3 C2 N2 O4 2.1(3) . . . . ?
C1 C2 N2 O4 -175.68(17) . . . . ?
C3 C2 N2 O3 179.6(2) . . . . ?
C1 C2 N2 O3 1.9(3) . . . . ?
C4 C5 N3 O5 2.3(3) . . . . ?
C1 C5 N3 O5 -177.24(17) . . . . ?
C4 C5 N3 O6 -179.3(2) . . . . ?
C1 C5 N3 O6 1.1(3) . . . . ?
