One-step amino-to-nitro transformation of carbonyl-containing fused-ring energetic compounds in nitric acid.
Miao, Xiangyan; Yu, Jiyuan; Li, Yuchuan; Pang, Siping; Organic & biomolecular chemistry 24 (2026) 1481–1487; doi:10.1039/d5ob01855b

data_7160988
_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 &amp; 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       '\f and \w 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/[\s^2^(Fo^2^)+(0.1588P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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'