A Study of Dinitro-bis-1,2,4-triazole-1,1'-diol and Derivatives: Design of High-Performance Insensitive Energetic Materials by the Introduction of N-Oxides
Alexander A. Dippold; Thomas M. Klapötke; Journal of the American Chemical Society 135 (2013) 9931–9938; doi:10.1021/ja404164j

data_4120039
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universit\"at
Butenandtstra\&se 5-13 (Haus D)
D-81377 M\"unchen
Bundesrepublik Deutschland
;
_publ_contact_author_email       tmk@cup.uni-muenchen.de
_publ_contact_author_fax         +49-89-2180-77491
_publ_contact_author_name        'Thomas M. Klapo\"tke'
_publ_contact_author_phone       +49-89-2180-77492
_publ_section_title
;
 A Study of Dinitro-bis-1,2,4-triazole-1,1'-diol and Derivatives: Design
 of High-Performance Insensitive Energetic Materials by the Introduction
 of N-Oxides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9931
_journal_page_last               9938
_journal_paper_doi               10.1021/ja404164j
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         '2(C4 N8 O6), 4(C H9 N6), H4 O2'
_chemical_formula_sum            'C12 H40 N40 O14'
_chemical_formula_weight         968.707
_chemical_name_common            (TAG)2-DNBTO
_chemical_name_systematic
'di(triaminoguanidinium) 3,3-dinitro-5,5-bis-1,2,4-triazole-1,1-diolate'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Alexander Dippold'
_audit_creation_date             21-Okt-11
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.70(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   26.168(5)
_cell_length_b                   3.5420(7)
_cell_length_c                   21.180(4)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      3.134
_cell_volume                     1859.5(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0319506
_diffrn_orient_matrix_UB_12      -0.0863131
_diffrn_orient_matrix_UB_13      0.0376109
_diffrn_orient_matrix_UB_21      -0.0162641
_diffrn_orient_matrix_UB_22      0.1096447
_diffrn_orient_matrix_UB_23      0.0326817
_diffrn_orient_matrix_UB_31      -0.0185023
_diffrn_orient_matrix_UB_32      -0.2454308
_diffrn_orient_matrix_UB_33      0.0013733
_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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5377
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         3.86
_diffrn_source_current           40
_diffrn_source_power             3.025
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.7301(6)
_exptl_crystal_description       rod
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.266
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          1.243
_refine_ls_shift/su_mean         0.081
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1015P)^2^+1.1598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                1229
_reflns_number_total             1695
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja404164j_si_008.cif
_cod_data_source_block           manuscript
_cod_original_cell_volume        1859.5(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4120039