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_7132055
_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 H3 N7 O4, H2 O'
_chemical_formula_sum            'C4 H5 N7 O5'
_chemical_formula_weight         231.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-11 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.137(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7059(7)
_cell_length_b                   10.5914(14)
_cell_length_c                   8.1537(9)
_cell_measurement_reflns_used    828
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      21.985
_cell_measurement_theta_min      3.156
_cell_volume                     405.79(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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  0.0762
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5248
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         1.923
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.7812.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 473 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1776
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0598P)^2^+0.2165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                1267
_reflns_number_total             1776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03330a2.cif
_cod_data_source_block           mo_20230329_ys_nlg_nh3oh329_0m
_cod_database_code               7132055
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
2.c Tetrahedral OH refined with riding coordinates:
 O4(H4)
;
_shelx_res_checksum              61265
_shelx_hkl_checksum              62017
_olex2_submission_special_instructions 'No special instructions were received'