Unraveling the reactivity of the azo bridge in 3,3′-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4′-azofurazanate in the synthesis of energetic compounds
Chen, Peng; Qiu, Lili; Yin, Ping; He, Chunlin; Pang, Siping; Shreeve, Jean’ne M.; Chemical Communications  (2022) –; doi:10.1039/D2CC00215A

data_7129686
_publ_section_title
;
 Unraveling the reactivity of the azo bridge in
 3,3&#x2032;-(5-dinitromethyl-1,2,4-oxadiazolyl)-4,4&#x2032;-azofurazanate
 in the synthesis of energetic compounds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00215A
_journal_year                    2022
_chemical_formula_moiety         'C5 H2 N7 O6, H2 O, H4 N'
_chemical_formula_sum            'C5 H8 N8 O7'
_chemical_formula_weight         292.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.575(3)
_cell_length_b                   11.854(2)
_cell_length_c                   6.6963(13)
_cell_measurement_reflns_used    3199
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.5179
_cell_volume                     1064.9(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      163.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2399
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.518
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0884
_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^)+(0.0298P)^2^+2.9639P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1947
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00215a2.cif
_cod_data_source_block           a_tw
_cod_database_code               7129686
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.794(7)
 0.206(7)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H,H) groups, All O(H,H) groups
3.a Riding coordinates:
 N7(H7A,H7B), O7(H7C,H7D), N8(H8A,H8B,H8C,H8D)
;
_olex2_submission_special_instructions 'No special instructions were received'