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_7134629
_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         'H2 O, 2(C6 H8 N10 O2), 3(C3 H7 N O)'
_chemical_formula_sum            'C21 H39 N23 O8'
_chemical_formula_weight         741.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-30
_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                90
_cell_angle_beta                 98.2810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.93420(10)
_cell_length_b                   14.6464(2)
_cell_length_c                   16.6514(2)
_cell_measurement_reflns_used    32031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2690
_cell_measurement_theta_min      3.8330
_cell_volume                     3362.88(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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  0.0725
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            60872
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.450
_diffrn_reflns_theta_min         3.872
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       blok
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6924
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0557P)^2^+3.0448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5707
_reflns_number_total             6924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02076j2.cif
_cod_data_source_block           jxe_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7134628--7134631.cif.'
_cod_database_code               7134629
_shelx_shelxl_version_number     2018/3
_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, All O(H,H) groups
2. Restrained distances
 C2-O3
 1.22 with sigma of 0.02
 C2-N4
 1.36 with sigma of 0.02
 N4-C5
 1.45 with sigma of 0.02
 N4-C6
 1.46 with sigma of 0.02
 C1-O1
 1.22 with sigma of 0.02
 C1-N1
 1.36 with sigma of 0.02
 N1-C3
 1.45 with sigma of 0.02
 N1-C4
 1.46 with sigma of 0.02
 C2-C5
 2.46 with sigma of 0.04
 C2-C6
 2.45 with sigma of 0.04
 C1-C3
 2.46 with sigma of 0.04
 C1-C4
 2.45 with sigma of 0.04
 N4-C5 \\sim N4-C6
 with sigma of 0.02
 N1-C3 \\sim N1-C4
 with sigma of 0.02
3. Restrained planarity
 C2, O3, N4, C5, C6
 with sigma of 0.1
 C1, O1, N1, C3, C4
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C2 \\sim O3 \\sim N4 \\sim C5 \\sim C6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C1 \\sim O1 \\sim N1 \\sim C3 \\sim C4: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C2, O3, N4, C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, O1, N1, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C2(0.74) H2(0.74) O3(0.74) N4(0.74) C5(0.74) H5A(0.74) H5B(0.74)
 H5C(0.74) C6(0.74) H6A(0.74) H6B(0.74) H6C(0.74) C1(0.26) H1(0.26) O1(0.26)
 N1(0.26) C3(0.26) H3A(0.26) H3B(0.26) H3C(0.26) C4(0.26) H4A(0.26) H4B(0.26)
 H4C(0.26)
7.a Free rotating group:
 O001(H00Q,H00R)
7.b Aromatic/amide H refined with riding coordinates:
 C016(H016), C017(H017), C2(H2), C1(H1)
7.c X=CH2 refined with riding coordinates:
 N00G(H00I,H00J), N00J(H00A,H00B), N00L(H00C,H00D), N00M(H00K,H00L), N00N(H00E,
 H00F), N00R(H00O,H00P)
7.d Idealised Me refined as rotating group:
 C01A(H01A,H01B,H01C), C01B(H01G,H01H,H01I), C01C(H01J,H01K,H01L), C01D(H01D,
 H01E,H01F), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              83972
_shelx_hkl_checksum              53863
_olex2_submission_special_instructions 'No special instructions were received'