Advanced tetracyclic heat-resistant energetic materials based on bis(4-nitropyrazole) bridged 1,2,4-triazole.
Chen, Luyao; Hu, Wei; Lei, Caijin; Zhu, Teng; Li, Chengchuang; Tang, Jie; Cheng, Guangbin; Xiao, Chuan; Yang, Hongwei; Dalton transactions (Cambridge, England : 2003) 53 (2024) 12641–12648; doi:10.1039/d4dt01627k

data_7716530
_publ_section_title
;
 Advanced tetracyclic heat-resistant energetic materials based on
 bis(4-nitropyrazole) bridged 1,2,4-triazole.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12641
_journal_page_last               12648
_journal_paper_doi               10.1039/d4dt01627k
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C10 H10 N16 O4, H2 O, 2(C2 H6 O S)'
_chemical_formula_sum            'C14 H24 N16 O7 S2'
_chemical_formula_weight         592.61
_chemical_name_systematic        123
_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     iterative
_audit_creation_date             2023-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-09 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                82.993(4)
_cell_angle_beta                 87.537(4)
_cell_angle_gamma                68.954(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4496(9)
_cell_length_b                   11.7533(13)
_cell_length_c                   12.2973(13)
_cell_measurement_reflns_used    2655
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      23.75
_cell_measurement_theta_min      2.36
_cell_volume                     1265.2(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0914
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17188
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.309
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.8535.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0064(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         4560
_refine_ls_number_restraints     1036
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0847
_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^)+(0.0300P)^2^+5.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2751
_reflns_number_total             4560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01627k2.cif
_cod_data_source_block           mo_20230505_zm_nlg_cly_2023_4
_cod_depositor_comments
'Adding full bibliography for 7716530--7716531.cif.'
_cod_database_code               7716530
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(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
 C14-S2
 1.8 with sigma of 0.002
 O6-H10B
 2.3 with sigma of 0.02
 S2-O6 \\sim S2A-O6A
 with sigma of 0.02
 S2-C13 \\sim S2A-C14A
 with sigma of 0.02
 O6-C13 \\sim O6A-C14A
 with sigma of 0.04
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
N5 \\sim N15 \\sim O6A \\sim C5 \\sim O3 \\sim N12 \\sim N4 \\sim H11B \\sim O4
\\sim C3 \\sim H12A \\sim C4 \\sim N14 \\sim N3 \\sim H11C \\sim C8 \\sim H14C
\\sim N8 \\sim N7 \\sim H14F \\sim N9 \\sim H13B \\sim H10A \\sim O6 \\sim H10B
\\sim H13A \\sim N11 \\sim S2 \\sim H7 \\sim H12D \\sim N6 \\sim H12C \\sim
H16A \\sim O5 \\sim N10 \\sim S1 \\sim C9 \\sim C10 \\sim C6 \\sim C14A \\sim
O10 \\sim C7 \\sim H13F \\sim O2 \\sim H11 \\sim H1A \\sim N13 \\sim H1B \\sim
N16 \\sim C1 \\sim O1 \\sim H13C \\sim H2A \\sim H16B \\sim N1 \\sim H12B \\sim
H2B \\sim C13 \\sim C2 \\sim H11A \\sim N2 \\sim C14 \\sim H12E \\sim S2A \\sim
H14B \\sim H14E \\sim H14A \\sim H13D \\sim C12 \\sim H13E \\sim H14D \\sim
C13A \\sim C11: within 2A with sigma of 0.02 and sigma for terminal atoms of
3.8 within 2A
Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(N5) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(N14) \\sim
Ueq, Uanis(O3) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(N4)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(N16) \\sim Ueq,
Uanis(C4) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(N7) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(N13) \\sim Ueq, Uanis(N10) \\sim Ueq,
Uanis(N11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(N9) \\sim Ueq, Uanis(S2A)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N1) \\sim Ueq,
Uanis(C9) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(N6) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(N8) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(O10)
\\sim Ueq, Uanis(N15) \\sim Ueq, Uanis(S2) \\sim Ueq, Uanis(C14A) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(O6A) \\sim Ueq, Uanis(N12) \\sim Ueq, Uanis(C13A)
\\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C14) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N12) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(N16) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(N15) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(N14) \\sim Ueq, Uanis(N11) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(N10)
\\sim Ueq, Uanis(N5) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(O3) \\sim Ueq, Uanis(N9) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(N3) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(N13) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(S2) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(C13A) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(O6A)
\\sim Ueq, Uanis(S2A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(N6) \\sim Ueq,
Uanis(N7) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(N8) \\sim
Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
5. Others
 Sof(S2A)=Sof(O6A)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14A)=Sof(H14D)=
 Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(S2)=Sof(O6)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=
 Sof(H14B)=Sof(H14C)=FVAR(1)
6.a Free rotating group:
 O10(H10A,H10B)
6.b Rotating group:
 N2(H2A,H2B), N12(H12A), N16(H16B)
6.c Aromatic/amide H refined with riding coordinates:
 N7(H7), N11(H11)
6.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C12(H12C,H12D,
 H12E), C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F)
;
_olex2_submission_special_instructions 'No special instructions were received'