Synthetic Routes to a Triazole and Tetrazole with Trinitroalkyl Substitution at Nitrogen.
Klapötke, Thomas M; Krumm, Burkhard; Reith, Thomas; Unger, Cornelia C.; The Journal of organic chemistry 83 (2018) 10505–10509; doi:10.1021/acs.joc.8b01072

data_4035068
_publ_section_title
;
 Synthetic Routes to a Triazole and Tetrazole with Trinitroalkyl
 Substitution at Nitrogen.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10505
_journal_page_last               10509
_journal_paper_doi               10.1021/acs.joc.8b01072
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C6 H2 N8 O6'
_chemical_formula_sum            'C6 H2 N8 O6'
_chemical_formula_weight         282.130
_chemical_name_common
1-(2,2,2-trinitroethyl)-1H-1,2,3-triazole-4,5-dicarbonitrile
_chemical_name_systematic
1-(2,2,2-trinitroethyl)-1H-1,2,3-triazole-4,5-dicarbonitrile
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Thu Oct 13 08:37:40 2016'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 108.644(8)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   10.933(7)
_cell_length_b                   9.353(5)
_cell_length_c                   11.274(9)
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4650
_cell_measurement_theta_min      4.5010
_cell_volume                     1092.3(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -75.00  -48.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   30.0000 27

  2 omega -108.00  -59.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   90.0000 49

  3 omega    2.00   66.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000   30.0000 64

  4 omega   -2.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000  -60.0000 104

  5 omega  -19.00   75.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  120.0000 94

  6 omega  -27.00  104.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932    0.0000  -60.0000 131

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      -0.0283453000
_diffrn_orient_matrix_UB_12      0.0275837000
_diffrn_orient_matrix_UB_13      -0.0612533000
_diffrn_orient_matrix_UB_21      0.0561410000
_diffrn_orient_matrix_UB_22      0.0415565000
_diffrn_orient_matrix_UB_23      0.0067927000
_diffrn_orient_matrix_UB_31      0.0270568000
_diffrn_orient_matrix_UB_32      -0.0571455000
_diffrn_orient_matrix_UB_33      -0.0246615000
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8407
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.29
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.7156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.047
_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     189
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.4218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                1517
_reflns_number_total             2221
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo8b01072_si_002.cif
_cod_data_source_block           manuscript
_cod_database_code               4035068