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_7160987
_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         'Cl O4, C5 H6 N9 O'
_chemical_formula_sum            'C5 H6 Cl N9 O5'
_chemical_formula_weight         307.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8115(3)
_cell_length_b                   10.1175(5)
_cell_length_c                   13.4986(5)
_cell_measurement_reflns_used    3341
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.51
_cell_volume                     1066.83(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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0837
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8345
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.347
_diffrn_reflns_theta_min         2.516
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1232 before and 0.0812 after correction.
The Ratio of minimum to maximum transmission is 0.7918.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 677 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0208P)^2^+0.7217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1869
_reflns_number_total             2168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01855b2.cif
_cod_data_source_block           2025167
_cod_database_code               7160987
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.953
_diffrn_oxdiff_ac3_digest_hkl    41853153c08b6aa6549a5fb3d39817a9bc52d3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 N9-H9B = N9-H9A = N1-H1B = N1-H1A
 0.87 with sigma of 0.02
 Cl1-O9 \\sim Cl1-O6 \\sim Cl1-O3 \\sim Cl1-O5 \\sim Cl1-O7 \\sim Cl1-O4
 with sigma of 0.02
3. Rigid bond restraints
 O3, O4, O5, O6, O7, O9
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
O3 \\sim O4 \\sim O5 \\sim O6 \\sim O7 \\sim O9: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 2A
5. Others
 Sof(O6)=Sof(O7)=Sof(O9)=1-FVAR(1)
 Sof(O3)=Sof(O4)=Sof(O5)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'