Trinitromethyl- and nitramino-substituted triazolo-pyridazines: synthesis and energetic performance
Nehe, Sagar; Yadav, Abhishek Kumar; Ghule, Vikas D.; Dharavath, Srinivas; Chemical Communications 61 (2025) 9047–9050; doi:10.1039/D5CC02368H

data_7134577
_publ_section_title
;
 Trinitromethyl- and nitramino-substituted triazolo-pyridazines: synthesis
 and energetic performance
;
_journal_issue                   50
_journal_name_full               'Chemical Communications'
_journal_page_first              9047
_journal_page_last               9050
_journal_paper_doi               10.1039/D5CC02368H
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C6 H2 Cl N7 O6'
_chemical_formula_sum            'C6 H2 Cl N7 O6'
_chemical_formula_weight         303.60
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-05-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2025-05-14 deposited with the CCDC.	2025-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                104.376(3)
_cell_angle_beta                 97.790(2)
_cell_angle_gamma                102.786(2)
_cell_formula_units_Z            4
_cell_length_a                   9.1720(8)
_cell_length_b                   9.4996(9)
_cell_length_c                   13.2063(12)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.30
_cell_volume                     1064.67(17)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22321
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         2.554
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1596 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.8490.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5319
_refine_ls_number_restraints     174
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0162P)^2^+0.9963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4540
_reflns_number_total             5319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02368h2.cif
_cod_data_source_block           9octb_0m_a_ccdc_2441110
_cod_depositor_comments
'Adding full bibliography for 7134576--7134577.cif.'
_cod_database_code               7134577
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.878
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{N13, N13A}
3. Restrained distances
 N14-C12 \\sim N14A-C12 \\sim N12A-C12 \\sim N12-C12 \\sim N13A-C12 \\sim
N13-C12
 with sigma of 0.01
 O9-C12 \\sim O9A-C12 \\sim C12-O014 \\sim C12-O0 \\sim C12-O8 \\sim C12-O8A
\\sim O11-C12 \\sim O11A-C12
 \\sim O10-C12 \\sim O10A-C12 \\sim O12-C12 \\sim O12A-C12
 with sigma of 0.04
 O8A-N12A \\sim O8-N12 \\sim O9A-N12A \\sim O9-N12 \\sim O10A-N13A \\sim
O10-N13 \\sim O11-N13 \\sim O11A-
 N13A \\sim O0-N14A \\sim O12A-N14A \\sim O12-N14 \\sim O014-N14
 with sigma of 0.01
 O11-O10 \\sim O11A-O10A \\sim O12-O014 \\sim O12A-O0 \\sim O9-O8 \\sim O9A-O8A
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Uanis(N12A) \\sim Ueq, Uanis(N12) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
Uanis(N13) = Uanis(N13A)
Uanis(N12A) = Uanis(N12)
Uanis(O9A) = Uanis(O9)
Uanis(O11) = Uanis(O11A)
5. Others
 Sof(N14A)=Sof(O12A)=Sof(O0)=Sof(O8A)=Sof(N12A)=Sof(O9A)=Sof(N13A)=Sof(O10A)=
 Sof(O11A)=1-FVAR(1)
 Sof(O9)=Sof(O12)=Sof(N13)=Sof(O11)=Sof(N12)=Sof(O10)=Sof(N14)=Sof(O8)=
 Sof(O014)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C8(H8)
;
_shelx_res_checksum              40353
_shelx_hkl_checksum              24688
_olex2_submission_special_instructions 'No special instructions were received'