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_7134628
_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         'C7 H8 N10 O4, C3 H7 N O'
_chemical_formula_sum            'C10 H15 N11 O5'
_chemical_formula_weight         369.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-05-12 deposited with the CCDC.	2025-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                81.897(6)
_cell_angle_beta                 87.036(6)
_cell_angle_gamma                79.394(6)
_cell_formula_units_Z            2
_cell_length_a                   6.6160(5)
_cell_length_b                   9.4274(7)
_cell_length_c                   12.6888(7)
_cell_measurement_reflns_used    3879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8170
_cell_measurement_theta_min      3.4930
_cell_volume                     769.86(9)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.2172
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7303
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         3.519
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.93670
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.12
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_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.792
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2697
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      0.787
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0841
_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^)+(0.0101P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1298
_reflns_number_total             2697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02076j2.cif
_cod_data_source_block           jxe
_cod_depositor_comments
'Adding full bibliography for 7134628--7134631.cif.'
_cod_original_cell_volume        769.87(9)
_cod_database_code               7134628
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N4, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C7) = Uanis(C6)
4. Rigid body (RIGU) restrains
 C7, C6, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5.a Aromatic/amide H refined with riding coordinates:
 C8(H8)
5.b X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N3(H3A,H3B), N7(H7A,H7B), N1(H1A,H1B)
5.c Idealised Me refined as rotating group:
 C9(H9C,H9D,H9E), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              32192
_shelx_hkl_checksum              40529
_olex2_submission_special_instructions 'No special instructions were received'