#------------------------------------------------------------------------------
#$Date: 2021-09-30 02:11:58 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/84/7708470.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7708470
loop_
_publ_author_name
'Klapötke, Thomas M.'
'Kofen, Moritz'
'Stierstorfer, Jörg'
_publ_section_title
;
   N-Functionalisation of 5,5′-bistetrazole providing
 2,2′-di(azidomethyl)bistetrazole: a melt-castable metal-free green
 primary explosive
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02731J
_journal_year                    2021
_chemical_formula_moiety         'C4 H4 N14'
_chemical_formula_sum            'C4 H4 N14'
_chemical_formula_weight         248.21
_chemical_name_common            2,2-diazidomethyl-5,5-bitetrazole
_chemical_name_systematic        2,2-diazidomethyl-5,5-bitetrazole
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      88
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-07-24
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-06 deposited with the CCDC.	2021-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1656(10)
_cell_length_b                   17.1656(10)
_cell_length_c                   6.7040(7)
_cell_measurement_reflns_used    830
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      23.2350
_cell_measurement_theta_min      3.3310
_cell_volume                     1975.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Encifer 1.5.1, CCDC 2014'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  33.00   1.00   45.00    --  -20.37  77.00 -30.00   26
  2  ω      3.00  50.00   1.00   45.00    --  -20.37  57.00-150.00   47
  3  ω    -47.00  45.00   1.00   45.00    --   21.23 -57.00 -60.00   92
  4  ω     -3.00  28.00   1.00   45.00    --   21.23  77.00  60.00   31
  5  ω     -5.00  25.00   1.00   45.00    --   21.23  77.00 -60.00   30
  6  ω     11.00  92.00   1.00   45.00    --   21.23  57.00  90.00   81
  7  ω    -20.00  65.00   1.00   45.00    --   21.23 -99.00-180.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0127459000
_diffrn_orient_matrix_UB_12      -0.0150484000
_diffrn_orient_matrix_UB_13      0.0929326000
_diffrn_orient_matrix_UB_21      0.0322596000
_diffrn_orient_matrix_UB_22      0.0178268000
_diffrn_orient_matrix_UB_23      0.0479086000
_diffrn_orient_matrix_UB_31      -0.0224731000
_diffrn_orient_matrix_UB_32      0.0341057000
_diffrn_orient_matrix_UB_33      0.0160389000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.1034
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6544
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         2.373
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0441
_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/[σ²(Fo²)+(0.0397P)²+0.4034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                698
_reflns_number_total             1009
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02731j2.cif
_cod_data_source_block           px270
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7708470
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.40178(10) 0.45249(9) 0.3012(2) 0.0227(4) Uani 1 1 d . . . . .
N1 N 0.47356(10) 0.47574(10) 0.2572(2) 0.0224(4) Uani 1 1 d . . . . .
N4 N 0.39544(10) 0.47094(10) -0.0098(2) 0.0261(4) Uani 1 1 d . . . . .
N3 N 0.35387(10) 0.44858(10) 0.1460(2) 0.0272(4) Uani 1 1 d . . . . .
N6 N 0.47208(12) 0.34871(10) 0.6227(3) 0.0316(5) Uani 1 1 d . . . . .
N5 N 0.40522(11) 0.35222(11) 0.5515(2) 0.0342(5) Uani 1 1 d . . . . .
C1 C 0.46770(11) 0.48666(11) 0.0612(3) 0.0206(5) Uani 1 1 d . . . . .
N7 N 0.53114(13) 0.33558(11) 0.6909(3) 0.0453(6) Uani 1 1 d . . . . .
C2 C 0.37863(14) 0.43051(14) 0.5035(3) 0.0282(5) Uani 1 1 d . . . . .
H2B H 0.4001(11) 0.4682(11) 0.590(3) 0.018(5) Uiso 1 1 d . . . . .
H2A H 0.3211(13) 0.4307(11) 0.506(3) 0.024(6) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 N3 114.53(15) . . ?
N1 N2 C2 122.40(17) . . ?
N3 N2 C2 123.04(17) . . ?
N2 N1 C1 101.06(15) . . ?
N3 N4 C1 105.93(15) . . ?
N4 N3 N2 105.67(15) . . ?
N7 N6 N5 171.2(2) . . ?
N6 N5 C2 114.76(18) . . ?
N1 C1 N4 112.81(17) . . ?
N1 C1 C1 123.0(2) . 9_665 ?
N4 C1 C1 124.2(2) . 9_665 ?
N5 C2 N2 110.97(17) . . ?
N5 C2 H2B 111.9(11) . . ?
N2 C2 H2B 106.8(11) . . ?
N5 C2 H2A 108.2(12) . . ?
N2 C2 H2A 106.8(11) . . ?
H2B C2 H2A 112.1(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 N1 1.328(2) . ?
N2 N3 1.328(2) . ?
N2 C2 1.463(2) . ?
N1 C1 1.331(2) . ?
N4 N3 1.322(2) . ?
N4 C1 1.356(2) . ?
N6 N7 1.135(2) . ?
N6 N5 1.245(3) . ?
N5 C2 1.455(3) . ?
C1 C1 1.454(4) 9_665 ?
C2 H2B 0.945(19) . ?
C2 H2A 0.99(2) . ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
? ? ? ? ? ? ? ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 N2 N1 C1 0.2(2) . . . . ?
C2 N2 N1 C1 178.19(18) . . . . ?
C1 N4 N3 N2 0.6(2) . . . . ?
N1 N2 N3 N4 -0.5(2) . . . . ?
C2 N2 N3 N4 -178.49(18) . . . . ?
N2 N1 C1 N4 0.2(2) . . . . ?
N2 N1 C1 C1 179.7(2) . . . 9_665 ?
N3 N4 C1 N1 -0.5(2) . . . . ?
N3 N4 C1 C1 -180.0(2) . . . 9_665 ?
N6 N5 C2 N2 87.8(2) . . . . ?
N1 N2 C2 N5 -78.6(2) . . . . ?
N3 N2 C2 N5 99.2(2) . . . . ?
