Synthesis of fused energetic compounds using the structural modification from local carbonyl to hydroxylamine/hydrazone
Lei, Caijin; Xiao, Chuan; Tang, Jie; Yang, Hongwei; Zhang, Qinghua; Cheng, Guangbin; Chemical Communications  (2023) –; doi:10.1039/D3CC03330A

data_7132057
_publ_section_title
;
 Synthesis of fused energetic compounds using the structural modification
 from local carbonyl to hydroxylamine/hydrazone
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03330A
_journal_year                    2023
_chemical_formula_moiety         'C4 H2 N7 O4, H4 N O'
_chemical_formula_sum            'C4 H6 N8 O5'
_chemical_formula_weight         246.17
_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             2019-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-11 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.483(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.715(2)
_cell_length_b                   11.775(4)
_cell_length_c                   10.892(4)
_cell_measurement_reflns_used    3913
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.425
_cell_measurement_theta_min      2.550
_cell_volume                     859.6(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10060
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.550
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1379 before and 0.0724 after correction. The Ratio of minimum to maximum transmission is 0.7990. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1558
_reflns_number_total             1977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03330a2.cif
_cod_data_source_block           22019474_0m
_cod_database_code               7132057
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N8-H8B = N8-H8A = N8-H8C
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.b Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'