Polynitro-Functionalized Azopyrazole with High Performance and Low Sensitivity as Novel Energetic Materials.
Zhang, Guojie; Yi, Zhenxin; Cheng, Guangbin; Yang, Wei; Yang, Hongwei; ACS applied materials & interfaces 14 (2022) 10594–10604; doi:10.1021/acsami.2c00154

data_4519324
_publ_section_title
;
 Polynitro-Functionalized Azopyrazole with High Performance and Low
 Sensitivity as Novel Energetic Materials.
;
_journal_issue                   8
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              10594
_journal_page_last               10604
_journal_paper_doi               10.1021/acsami.2c00154
_journal_volume                  14
_journal_year                    2022
_chemical_formula_moiety         'C6 N10 O8, 2(H2 O), 2(H4 N)'
_chemical_formula_sum            'C6 H12 N12 O10'
_chemical_formula_weight         412.28
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.457(3)
_cell_angle_beta                 92.636(3)
_cell_angle_gamma                99.304(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1996(7)
_cell_length_b                   10.1924(10)
_cell_length_c                   11.2601(11)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.288
_cell_measurement_theta_min      2.473
_cell_volume                     796.55(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      173.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.974
_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
_diffrn_reflns_av_unetI/netI     0.2106
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_number            3573
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.472
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.745553
_exptl_absorpt_correction_T_min  0.627631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 12124 reflections, Rint = 0.0712
 (4627 with I > 3sig(I), Rint = 0.0444)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1825
_refine_ls_R_factor_gt           0.0862
_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^)+(0.0828P)^2^+0.3720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.2015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1869
_reflns_number_total             3573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am2c00154_si_005.cif
_cod_data_source_block           22019795_0m_4
_cod_database_code               4519324
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All N(H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O10-H10B
 0.84 with sigma of 0.02
 H10B-H10A
 1.46 with sigma of 0.02
 N12-H12A \\sim N12-H12B \\sim N12-H12C \\sim N12-H12D
 with sigma of 0.02
 N11-H11C \\sim N11-H11D \\sim N11-H11B \\sim N11-H11A
 with sigma of 0.02
3.a Free rotating group:
 O9(H9A,H9B), O10(H10A), N11(H11A,H11B), N12(H12A,H12B)
;
_olex2_submission_special_instructions 'No special instructions were received'