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_7236634
_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 H N10 O2, H4 N, H2 O'
_chemical_formula_sum            'C2 H7 N11 O3'
_chemical_formula_weight         233.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-02-23 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.96(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.663(9)
_cell_length_b                   16.418(17)
_cell_length_c                   16.589(17)
_cell_measurement_reflns_used    621
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.73
_cell_measurement_theta_min      2.48
_cell_volume                     1787(4)
_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 0.970
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9118
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         1.758
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0368 before and 0.0274 after correction. The Ratio of minimum to maximum transmission is 0.8441. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0545
_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^)+(0.1249P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2173
_reflns_number_total             3160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ta05905a2.cif
_cod_data_source_block           mo_2016736-wbs4-298k_0ma
_cod_original_cell_volume        1787(3)
_cod_database_code               7236634
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All N(H,H) groups, All O(H,H) groups
2. Restrained distances
 N8-H8
 0.85 with sigma of 0.02
 H19-N19
 0.85 with sigma of 0.02
 N22-H22B = N22-H22D = N22-H22A = N22-H22C
 0.86 with sigma of 0.02
 H22B-H22D
 1.46 with sigma of 0.02
 N11-H11C = N11-H11A = N11-H11B
 0.86 with sigma of 0.02
 N11-H11D
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N11) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N11) \\sim Ueq, Uanis(N22) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Free rotating group:
 N22(H22A,H22B), O1W(H1WA,H1WB), N11(H11A,H11B), O2W(H2WA,H2WB)
;
_olex2_submission_special_instructions 'No special instructions were received'