Nitrogen-Rich Tetrazolo[1,5-b]pyridazine: Promising Building Block for Advanced Energetic Materials.
Huang, Wei; Tang, Yongxing; Imler, Gregory H.; Parrish, Damon A.; Shreeve, Jean'ne M.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c00161

data_4134134
_publ_section_title
;
 Nitrogen-Rich Tetrazolo[1,5-b]pyridazine: Promising Building Block for
 Advanced Energetic Materials.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00161
_journal_year                    2020
_chemical_formula_moiety         'C4 H2 Cl N6 O, H5 N2, H2 O'
_chemical_formula_sum            'C4 H9 Cl N8 O2'
_chemical_formula_weight         236.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.828(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.876(2)
_cell_length_b                   19.258(3)
_cell_length_c                   3.7520(7)
_cell_measurement_reflns_used    830
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      3.55
_cell_volume                     930.3(3)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5605
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_min         1.903
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear brown'
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 629 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0425P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.707
_reflns_number_gt                1808
_reflns_number_total             2370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00161_si_004.cif
_cod_data_source_block           shrv762_a
_cod_original_sg_symbol_H-M      'C m'
_cod_database_code               4134134
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.880
_shelx_estimated_absorpt_t_max   0.992