Combination of 5-amino-4-nitro-1,2-dihydro-3<i>H</i>-pyrazol-3-one and azine frameworks for insensitive, heat-resistant energetic materials.
Jiang, Xiu'e; Wang, Ruihui; Fan, Mingren; Song, Siwei; Wang, Yi; Zhang, Qinghua; Dalton transactions (Cambridge, England : 2003) 54 (2025) 7056–7061; doi:10.1039/d5dt00488h

data_7718436
_publ_section_title
;
 Combination of 5-amino-4-nitro-1,2-dihydro-3<i>H</i>-pyrazol-3-one and
 azine frameworks for insensitive, heat-resistant energetic materials.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7056
_journal_page_last               7061
_journal_paper_doi               10.1039/d5dt00488h
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         '4(Cl H O4), 6(C8 H6 N12 O6), 10(H2 O)'
_chemical_formula_sum            'C48 H60 Cl4 N72 O62'
_chemical_formula_weight         2779.48
_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             2024-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-10-10 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                118.314(2)
_cell_angle_beta                 108.221(2)
_cell_angle_gamma                90.012(2)
_cell_formula_units_Z            1
_cell_length_a                   10.5731(5)
_cell_length_b                   16.0518(8)
_cell_length_c                   16.8857(13)
_cell_measurement_reflns_used    3626
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.54
_cell_volume                     2358.3(3)
_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
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0696
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24520
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         2.061
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1288 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.7463. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.164
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.090
_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     903
_refine_ls_number_reflns         8358
_refine_ls_number_restraints     341
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.0872
_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^)+(0.1031P)^2^+7.8452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2110
_refine_ls_wR_factor_ref         0.2735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3891
_reflns_number_total             8358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00488h2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7718434--7718437.cif.'
_cod_original_cell_volume        2358.3(2)
_cod_database_code               7718436
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.961
_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 O(H,H) groups
2. Restrained distances
 O8-H8
 0.88 with sigma of 0.02
 O22-H22
 0.88 with sigma of 0.02
 Cl00-H22
 2 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O10 \\sim O10A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
O7A \\sim O7: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O9 \\sim O9A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O8A \\sim O8: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C18) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O29) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O31) \\sim Ueq, Uanis(O32) \\sim Ueq, Uanis(O33) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(O10A) \\sim Ueq, Uanis(O10) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O7A) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O9) \\sim Ueq, Uanis(O9A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O8) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O9) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O8) \\sim Ueq, Uanis(O8A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O27) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: O10(0.8) O7(0.8) O8(0.8) O9(0.8) O30(0.5) H30A(0.5) H30B(0.5)
 O31(0.5) H31A(0.5) H31B(0.5) O32(0.5) H32C(0.5) H32D(0.5) O33(0.5) H33A(0.5)
 H33B(0.5) O10A(0.2) O7A(0.2) O9A(0.2) O8A(0.2)
6.a Riding coordinates:
 O27(H27C,H27D), O28(H28A,H28B), O29(H29A,H29B), O30(H30A,H30B), O31(H31A,
 H31B), O33(H33A,H33B)
6.b Free rotating group:
 O32(H32C,H32D)
6.c Aromatic/amide H refined with riding coordinates:
 N21(H21), N25(H25), N33(H33), N10(H10), N16(H16), N4(H4)
6.d X=CH2 refined with riding coordinates:
 N20(H20A,H20B), N27(H27A,H27B), N13(H13A,H13B), N2(H2A,H2B), N11(H11A,H11B),
 N32(H32A,H32B)
;
_shelx_res_checksum              27506
_shelx_hkl_checksum              91624
_olex2_submission_special_instructions 'No special instructions were received'