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_7160989
_publ_section_title
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 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 H N6 O4, 3(H2 O), H4 N'
_chemical_formula_sum            'C4 H11 N7 O7'
_chemical_formula_weight         269.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-11-10 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                67.746(3)
_cell_angle_beta                 88.999(3)
_cell_angle_gamma                87.729(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5845(6)
_cell_length_b                   8.3838(7)
_cell_length_c                   10.3193(8)
_cell_measurement_reflns_used    1511
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.146
_cell_measurement_theta_min      2.627
_cell_volume                     526.81(8)
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5802
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.627
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.7490.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0656
_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^)+(0.1011P)^2^+0.3601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.2157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1247
_reflns_number_total             2113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01855b2.cif
_cod_data_source_block           mo_20242050_0m
_cod_database_code               7160989
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Restrained distances
 O5-H5B = O5-H5A = N7-H7B = N7-H7D = N7-H7C = N7-H7A = O6-H6B = O6-H6A = O7-
 H7E = O7-H7F
 0.87 with sigma of 0.02
;
_olex2_submission_special_instructions 'No special instructions were received'