Benzimidazole-based low-sensitivity and heat-resistant energetic materials: design and synthesis
Liang, Ying; Hu, Xian-Kun; Yang, Zhang-Lei; Liu, Miao-Miao; Zhang, Yao; Wu, Jin-Ting; Zhang, Jian-Guo; Zhao, Ting-Xing; Sun, Shan-Hu; Wang, Shu-Min; New Journal of Chemistry 49 (2025) 257–262; doi:10.1039/D4NJ04471A

data_7063565
_publ_section_title
;
 Benzimidazole-based low-sensitivity and heat-resistant energetic
 materials: design and synthesis
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              257
_journal_page_last               262
_journal_paper_doi               10.1039/D4NJ04471A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C2 H6 O S, C7 H6 N6 O4'
_chemical_formula_sum            'C9 H12 N6 O5 S'
_chemical_formula_weight         316.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2024-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.257(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.756(3)
_cell_length_b                   4.6794(5)
_cell_length_c                   19.632(2)
_cell_measurement_reflns_used    1110
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      25.805
_cell_measurement_theta_min      2.536
_cell_volume                     2549.8(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8229
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.075
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0976 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.6753.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     178
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0731
_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^)+(0.0284P)^2^+17.5938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1542
_reflns_number_total             2581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj04471a2.cif
_cod_data_source_block           12515_0m
_cod_depositor_comments          'Adding full bibliography for 7063565.cif.'
_cod_database_code               7063565
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C9A \\sim S1-C9
 with sigma of 0.001
 C8A-S1A \\sim C8-S1
 with sigma of 0.001
 C8A-S1A \\sim S1A-C9A
 with sigma of 0.001
 H8AA-O2 \\sim O2-H8AB
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(S1) = Uanis(S1A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(S1A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(H9AC)=1-FVAR(1)
 Sof(S1)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7)
6.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N5(H5A,H5B)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'