Polynitro-1,2,4-triazole-functionalized azo-furazans as high-performance and insensitive energetic materials
Ma, Jinchao; Zhang, Guojie; Gu, Hao; Tang, Jie; Wang, Bohan; Yang, Hongwei; Cheng, Guangbin; New Journal of Chemistry 43 (2019) 8370–; doi:10.1039/C9NJ01065C

data_7058351
_publ_section_title
;
 Polynitro-1,2,4-triazole-functionalized azo-furazans as high-performance
 and insensitive energetic materials
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8370
_journal_paper_doi               10.1039/C9NJ01065C
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C16 H16 N12 O6'
_chemical_formula_sum            'C16 H16 N12 O6'
_chemical_formula_weight         472.41
_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'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-09 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.057(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0217(11)
_cell_length_b                   27.895(6)
_cell_length_c                   15.205(3)
_cell_measurement_reflns_used    1049
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.249
_cell_measurement_theta_min      2.921
_cell_volume                     2113.8(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.979
_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  0.0487
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6766
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.475
_diffrn_reflns_theta_min         1.460
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0697 before and 0.0543 after correction. The Ratio of minimum to maximum transmission is 0.8638. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     650
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0465P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.719
_reflns_Friedel_fraction_max     0.684
_reflns_number_gt                2432
_reflns_number_total             3648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj01065c2.cif
_cod_data_source_block           mo_20180796-mjc-c_0m
_cod_depositor_comments          'Adding full bibliography for 7058351.cif.'
_cod_database_code               7058351
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 4(3)
 -3(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C18-O6 \\sim C2-O6
 with sigma of 0.02
 C1-C2 \\sim C18-C17
 with sigma of 0.02
4. 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
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C2) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
6. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: C2(0.5) H2A(0.5) H2B(0.5) C18(0.5) H18A(0.5) H18B(0.5) C17(0.5)
 H17A(0.5) H17B(0.5) H17C(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5)
8.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C4(H4A,H4B), C2(H2A,H2B), C18(H18A,H18B)
8.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N11(H11)
8.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'