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_7129687
_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         'C10 N14 O12, 2(H4 N), 2(H2 O)'
_chemical_formula_sum            'C10 H12 N16 O14'
_chemical_formula_weight         580.36
_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             2019-01-03
_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                 92.06(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0442(10)
_cell_length_b                   13.949(3)
_cell_length_c                   15.122(3)
_cell_measurement_reflns_used    3624
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.4598
_cell_volume                     1063.3(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      153.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_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_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7140
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.066
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0567P)^2^+0.7237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             2425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00215a2.cif
_cod_data_source_block           bwn18490
_cod_original_cell_volume        1063.4(4)
_cod_database_code               7129687
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O9A \\sim O9: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(O9A) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(O9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(1)
 Sof(O9)=Sof(H9A)=Sof(H9B)=FVAR(1)
4.a Riding coordinates:
 N8(H8A,H8B,H8C,H8D), O9(H9A,H9B), O9A(H9AA,H9AB)
;
_olex2_submission_special_instructions 'No special instructions were received'