#------------------------------------------------------------------------------
#$Date: 2026-02-19 03:08:52 +0100 (Thu 19 de Feb de 2026) $
#$Revision: 304534 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/09/7160988.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_7160988
loop_
_publ_author_name
'Miao, Xiangyan'
'Yu, Jiyuan'
'Li, Yuchuan'
'Pang, Siping'
_publ_section_title
;
 One-step amino-to-nitro transformation of carbonyl-containing fused-ring
 energetic compounds in nitric acid.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1481
_journal_page_last               1487
_journal_paper_doi               10.1039/d5ob01855b
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C4 H2 N6 O4, H2 O'
_chemical_formula_sum            'C4 H4 N6 O5'
_chemical_formula_weight         216.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-12-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-11 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.830(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1923(10)
_cell_length_b                   5.1853(4)
_cell_length_c                   13.3376(12)
_cell_measurement_reflns_used    969
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.54
_cell_measurement_theta_min      2.28
_cell_volume                     771.30(11)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_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
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1491
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         2.283
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.745372
_exptl_absorpt_correction_T_min  0.531235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1012 before and 0.0679 after correction.
 
For component 2:
 wR2(int) was 0.1108 before and 0.0691 after correction.
 The Ratio of minimum to maximum transmission is 0.71.

Final HKLF 4 output contains 7495 reflections, Rint = 0.0976
 (3253 with I > 3sig(I), Rint = 0.0713)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0766
_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)+(0.1588P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1046
_reflns_number_total             1491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01855b2.cif
_cod_data_source_block           mo_20242098_0m_4
_cod_database_code               7160988
_shelx_shelxl_version_number     2019/3
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.58311
 0.41689
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O3 O 0.7809(4) 0.3866(7) 0.4552(3) 0.0277(11) Uani 1 1 d . . . . .
O5 O 0.3759(3) 1.1188(7) 0.5940(3) 0.0244(10) Uani 1 1 d G . . . .
H5A H 0.378038 1.228317 0.544770 0.037 Uiso 1 1 d G U . . .
H5B H 0.311292 1.158681 0.622462 0.037 Uiso 1 1 d G U . . .
O2 O 0.5635(3) 0.0564(7) 0.8544(3) 0.0274(11) Uani 1 1 d . . . . .
O1 O 0.3159(3) 0.7476(8) 0.7879(3) 0.0246(10) Uani 1 1 d . . . . .
O4 O 0.8414(4) 0.0679(8) 0.5515(3) 0.0304(11) Uani 1 1 d . . . . .
N4 N 0.6238(4) 0.5460(8) 0.5853(3) 0.0184(11) Uani 1 1 d . . . . .
N3 N 0.5930(4) 0.3288(8) 0.7230(4) 0.0203(11) Uani 1 1 d . . . . .
N2 N 0.4665(4) 0.6795(7) 0.6872(3) 0.0181(11) Uani 1 1 d . . . . .
H2 H 0.447491 0.817505 0.650847 0.022 Uiso 1 1 calc R U . . .
N6 N 0.7799(4) 0.2602(8) 0.5315(3) 0.0207(11) Uani 1 1 d . . . . .
N5 N 0.6829(4) 0.1966(8) 0.6827(4) 0.0208(11) Uani 1 1 d . . . . .
N1 N 0.4395(4) 0.4026(8) 0.8209(4) 0.0221(12) Uani 1 1 d . . . . .
H1 H 0.397686 0.361339 0.871522 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4007(5) 0.6196(10) 0.7672(4) 0.0196(12) Uani 1 1 d . . . . .
C8 C 0.5589(5) 0.5321(10) 0.6635(4) 0.0194(12) Uani 1 1 d . . . . .
C9 C 0.6945(5) 0.3355(10) 0.6036(4) 0.0199(12) Uani 1 1 d . . . . .
C7 C 0.5339(5) 0.2434(10) 0.8062(4) 0.0202(12) 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
H5A O5 H5B 104.5 . . ?
C8 N4 C9 99.5(4) . . ?
N5 N3 C7 124.2(4) . . ?
C8 N3 N5 109.9(4) . . ?
C8 N3 C7 125.3(4) . . ?
C6 N2 H2 119.2 . . ?
C8 N2 H2 119.2 . . ?
C8 N2 C6 121.6(4) . . ?
O3 N6 O4 125.3(4) . . ?
O3 N6 C9 117.4(4) . . ?
O4 N6 C9 117.3(4) . . ?
C9 N5 N3 99.8(4) . . ?
C6 N1 H1 115.5 . . ?
C7 N1 H1 115.5 . . ?
C7 N1 C6 129.0(5) . . ?
O1 C6 N2 122.2(5) . . ?
O1 C6 N1 123.1(5) . . ?
N2 C6 N1 114.7(5) . . ?
N4 C8 N3 111.0(5) . . ?
N4 C8 N2 129.7(5) . . ?
N2 C8 N3 119.3(4) . . ?
N4 C9 N6 119.9(5) . . ?
N5 C9 N4 119.9(5) . . ?
N5 C9 N6 120.2(5) . . ?
O2 C7 N3 123.5(5) . . ?
O2 C7 N1 126.5(5) . . ?
N1 C7 N3 110.0(4) . . ?
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
O3 N6 1.211(6) . ?
O5 H5A 0.8700 . ?
O5 H5B 0.8699 . ?
O2 C7 1.195(6) . ?
O1 C6 1.209(6) . ?
O4 N6 1.228(6) . ?
N4 C8 1.322(7) . ?
N4 C9 1.358(7) . ?
N3 N5 1.365(6) . ?
N3 C8 1.355(7) . ?
N3 C7 1.409(7) . ?
N2 H2 0.8800 . ?
N2 C6 1.382(7) . ?
N2 C8 1.345(7) . ?
N6 C9 1.465(7) . ?
N5 C9 1.293(7) . ?
N1 H1 0.8800 . ?
N1 C6 1.384(7) . ?
N1 C7 1.368(7) . ?
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
O3 N6 C9 N4 -2.6(7) . . . . ?
O3 N6 C9 N5 174.8(5) . . . . ?
O4 N6 C9 N4 -179.8(5) . . . . ?
O4 N6 C9 N5 -2.4(7) . . . . ?
N3 N5 C9 N4 0.2(6) . . . . ?
N3 N5 C9 N6 -177.2(5) . . . . ?
N5 N3 C8 N4 -1.2(6) . . . . ?
N5 N3 C8 N2 176.4(5) . . . . ?
N5 N3 C7 O2 6.2(9) . . . . ?
N5 N3 C7 N1 -173.0(5) . . . . ?
C6 N2 C8 N4 173.1(5) . . . . ?
C6 N2 C8 N3 -4.1(8) . . . . ?
C6 N1 C7 O2 -179.5(5) . . . . ?
C6 N1 C7 N3 -0.3(8) . . . . ?
C8 N4 C9 N6 176.5(5) . . . . ?
C8 N4 C9 N5 -0.9(7) . . . . ?
C8 N3 N5 C9 0.6(5) . . . . ?
C8 N3 C7 O2 176.6(5) . . . . ?
C8 N3 C7 N1 -2.6(8) . . . . ?
C8 N2 C6 O1 -178.4(5) . . . . ?
C8 N2 C6 N1 1.5(7) . . . . ?
C9 N4 C8 N3 1.2(6) . . . . ?
C9 N4 C8 N2 -176.1(5) . . . . ?
C7 N3 N5 C9 172.3(5) . . . . ?
C7 N3 C8 N4 -172.8(5) . . . . ?
C7 N3 C8 N2 4.8(8) . . . . ?
C7 N1 C6 O1 -179.3(5) . . . . ?
C7 N1 C6 N2 0.8(8) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.58311
2 0.41689
