Facile synthesis of bicyclic heat-resistant energetic materials via a C–N coupling strategy
Jiang, Xiu’e; Fan, Mingren; Wang, Ruihui; Wang, Yi; Zhang, Qinghua; Chemical Communications 61 (2025) 9924–9927; doi:10.1039/D5CC02076J

data_7134631
_publ_section_title
;
 Facile synthesis of bicyclic heat-resistant energetic materials via a
 C--N coupling strategy
;
_journal_issue                   54
_journal_name_full               'Chemical Communications'
_journal_page_first              9924
_journal_page_last               9927
_journal_paper_doi               10.1039/D5CC02076J
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(Cl O4), C5 H10 N10'
_chemical_formula_sum            'C5 H10 Cl2 N10 O8'
_chemical_formula_weight         409.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-01
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2025-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                92.785(3)
_cell_angle_beta                 90.887(3)
_cell_angle_gamma                103.678(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2784(7)
_cell_length_b                   9.1672(7)
_cell_length_c                   9.3028(7)
_cell_measurement_reflns_used    2212
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.29
_cell_volume                     684.89(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       '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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.1129
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8963
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.600
_diffrn_reflns_theta_min         2.193
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1315 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.8014.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_description       blok
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0396P)^2^+0.9181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2103
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02076j2.cif
_cod_data_source_block           jxe_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7134628--7134631.cif.'
_cod_database_code               7134631
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2. Restrained distances
 O003-O003_$1
 3 with sigma of 0.05
3.a Aromatic/amide H refined with riding coordinates:
 N00B(H00B), N00G(H00G)
3.b X=CH2 refined with riding coordinates:
 N00E(H00A,H00C), N00H(H00D,H00E), N00I(H00F,H00H)
;
_shelx_res_checksum              6910
_shelx_hkl_checksum              23285
_olex2_submission_special_instructions 'No special instructions were received'