Construction of heterocycle-triazolotriazine framework energetic compounds: towards novel high-performance explosives.
Yang, Pengju; Zheng, Xiaoxiao; Zhang, Guojie; Lei, Caijing; Cheng, Guangbin; Yang, Hongwei; Chemical communications (Cambridge, England) 60 (2024) 10588–10591; doi:10.1039/d4cc03260h

data_7133573
_publ_section_title
;
 Construction of heterocycle-triazolotriazine framework energetic
 compounds: towards novel high-performance explosives.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10588
_journal_page_last               10591
_journal_paper_doi               10.1039/d4cc03260h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C6 H4 N10 O3, C3 H7 N O'
_chemical_formula_sum            'C9 H11 N11 O4'
_chemical_formula_weight         337.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-15 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.803(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.451(7)
_cell_length_b                   4.6905(10)
_cell_length_c                   20.015(4)
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.32
_cell_volume                     2834.1(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker D8 VENTURE'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_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  0.0702
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13132
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.443
_diffrn_reflns_theta_min         2.322
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8964.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0422P)^2^+1.7135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1904
_reflns_number_total             2866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03260h2.cif
_cod_data_source_block           mo_20211241_0m
_cod_depositor_comments
'Adding full bibliography for 7133573--7133575.cif.'
_cod_original_cell_volume        2834.2(10)
_cod_database_code               7133573
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Restrained distances
 N11-C10 \\sim N11-C7
 with sigma of 0.02
2. Rigid bond restraints
 C10, C7
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
3. Uiso/Uaniso restraints and constraints
C7 \\sim C10: within 2A with sigma of 0.008 and sigma for terminal atoms of
0.016 within 2A
4. Others
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=1-FVAR(1)
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9)
5.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
5.c Idealised Me refined as rotating group:
 C8(H8C,H8D,H8E), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'