Synthesis of 1-(2H-tetrazol-5-yl)-5-nitraminotetrazole and its derivatives from 5-aminotetrazole and cyanogen azide: a promising strategy towards the development of C–N linked bistetrazolate energetic materials
Wang, Binshen; Qi, Xiujuan; Zhang, Wenquan; Wang, Kangcai; Li, Wei; Zhang, Qinghua; J. Mater. Chem. A 5 (2017) 20867–; doi:10.1039/C7TA05905A

data_7236631
_publ_section_title
;
 Synthesis of 1-(2H-tetrazol-5-yl)-5-nitraminotetrazole and its
 derivatives from 5-aminotetrazole and cyanogen azide: a promising
 strategy towards the development of C--N linked bistetrazolate energetic
 materials
;
_journal_issue                   39
_journal_name_full               'J. Mater. Chem. A'
_journal_page_first              20867
_journal_paper_doi               10.1039/C7TA05905A
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C2 N10 O2, 2(H4 N O), H2 O'
_chemical_formula_sum            'C2 H10 N12 O5'
_chemical_formula_weight         282.22
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2017-02-23 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                96.566(2)
_cell_angle_beta                 99.093(2)
_cell_angle_gamma                107.015(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7628(8)
_cell_length_b                   8.4720(9)
_cell_length_c                   8.6864(9)
_cell_measurement_reflns_used    2650
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.41
_cell_volume                     531.54(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      170
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5493
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.429
_diffrn_reflns_theta_min         2.410
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0603 before and 0.0430 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
The \l/2 correction factor is 0.0015.
;
_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    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+0.1009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2080
_reflns_number_total             2363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ta05905a2.cif
_cod_data_source_block           mo_2016770_0m
_cod_database_code               7236631
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N12(H12A,H12B)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              54498
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'