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_7718437
_publ_section_title
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 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.
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_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_absolute_configuration ad
_chemical_formula_moiety         'Cl O3.97, C9 H9 N12 O6'
_chemical_formula_sum            'C9 H9 Cl N12 O9.97'
_chemical_formula_weight         480.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2024-10-10 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.011(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6357(6)
_cell_length_b                   5.8232(3)
_cell_length_c                   18.7157(9)
_cell_measurement_reflns_used    9063
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.489
_cell_measurement_theta_min      2.210
_cell_volume                     1678.12(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      302.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22346
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             975
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0870P)^2^+0.9230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                3462
_reflns_number_total             3773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5dt00488h2.cif
_cod_data_source_block           1_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7718434--7718437.cif.'
_cod_original_cell_volume        1678.12(13)
_cod_database_code               7718437
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N005(H005), N00B(H00B), N00E(H00E)
2.b X=CH2 refined with riding coordinates:
 N00G(H00a,H00c), N00L(H00d,H00f), N00P(H00g,H00h)
;
_olex2_submission_special_instructions 'No special instructions were received'