#------------------------------------------------------------------------------
#$Date: 2021-09-30 02:11:58 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/84/7708469.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_7708469
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 N10 O6'
_chemical_formula_sum            'C4 H4 N10 O6'
_chemical_formula_weight         288.17
_chemical_name_common            2,2-dinitratomethyl-5,5-bitetrazole
_chemical_name_systematic        2,2-dinitratomethyl-5,5-bitetrazole
_space_group_IT_number           114
_space_group_name_Hall           'P -4 2n'
_space_group_name_H-M_alt        'P -4 21 c'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      114
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-07-01
_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            4
_cell_length_a                   9.44290(10)
_cell_length_b                   9.44290(10)
_cell_length_c                   12.3008(3)
_cell_measurement_reflns_used    7011
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      32.0890
_cell_measurement_theta_min      2.6900
_cell_volume                     1096.84(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (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      108(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 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  44.00   1.00   15.00    --  -23.53  57.00 -30.00   84
  2  ω     18.00  71.00   1.00   15.00    --   24.78  57.00 -30.00   53
  3  ω      2.00  90.00   1.00   15.00    --   24.78  70.00 100.00   88
  4  ω     15.00  87.00   1.00   15.00    --   24.78  57.00  30.00   72
  5  ω     22.00  91.00   1.00   15.00    --   24.78  57.00 -90.00   69
  6  ω    -20.00  64.00   1.00   15.00    --   24.78 -99.00  60.00   84
  7  ω      8.00  91.00   1.00   15.00    --   24.78  57.00-150.00   83
  8  ω    -32.00  -7.00   1.00   15.00    --   24.78 131.00-141.59   25
  9  ω    -43.00  16.00   1.00   15.00    --   24.78 -37.00  90.00   59
 10  ω    -20.00  64.00   1.00   15.00    --   24.78 -99.00-180.00   84
 11  ω    -39.00  52.00   1.00   15.00    --   24.78 -77.00-120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0545359000
_diffrn_orient_matrix_UB_12      -0.0168484000
_diffrn_orient_matrix_UB_13      0.0374903000
_diffrn_orient_matrix_UB_21      0.0094920000
_diffrn_orient_matrix_UB_22      0.0665175000
_diffrn_orient_matrix_UB_23      0.0257524000
_diffrn_orient_matrix_UB_31      -0.0507721000
_diffrn_orient_matrix_UB_32      0.0305208000
_diffrn_orient_matrix_UB_33      -0.0354635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22865
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.757
_diffrn_reflns_theta_min         2.719
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.323
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0304
_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)+(0.0458P)²+0.1267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                1764
_reflns_number_total             1950
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02731j2.cif
_cod_data_source_block           px248
_cod_original_cell_volume        1096.84(4)
_cod_database_code               7708469
_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   0.923
_shelx_estimated_absorpt_t_max   0.950
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'
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
O1 O 0.81086(11) 0.14021(12) 0.53433(9) 0.0231(2) Uani 1 1 d . . . . .
O2 O 0.63582(13) 0.05465(14) 0.42884(11) 0.0328(3) Uani 1 1 d . . . . .
O3 O 0.84119(14) 0.10962(13) 0.36026(10) 0.0316(3) Uani 1 1 d . . . . .
N2 N 0.60910(13) 0.23027(12) 0.62491(10) 0.0206(2) Uani 1 1 d . . . . .
N1 N 0.64050(13) 0.36720(13) 0.62291(10) 0.0206(2) Uani 1 1 d . . . . .
N5 N 0.75465(14) 0.09653(14) 0.43147(10) 0.0232(3) Uani 1 1 d . . . . .
N3 N 0.47204(13) 0.20223(14) 0.63498(11) 0.0234(2) Uani 1 1 d . . . . .
N4 N 0.40823(13) 0.32577(13) 0.63987(11) 0.0230(2) Uani 1 1 d . . . . .
C1 C 0.51248(14) 0.42401(14) 0.63185(11) 0.0189(2) Uani 1 1 d . . . . .
C2 C 0.71613(15) 0.11876(16) 0.62220(13) 0.0227(3) Uani 1 1 d . . . . .
H2A H 0.672(2) 0.031(2) 0.6220(17) 0.023(5) Uiso 1 1 d . . . . .
H2B H 0.769(2) 0.120(2) 0.6844(18) 0.027(5) 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'
O O 0.0106 0.0060 '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
C2 O1 N5 113.48(11) . . ?
N1 N2 N3 114.47(12) . . ?
N1 N2 C2 123.21(12) . . ?
N3 N2 C2 122.24(12) . . ?
N2 N1 C1 100.88(11) . . ?
O2 N5 O3 130.85(14) . . ?
O2 N5 O1 117.97(12) . . ?
O3 N5 O1 111.19(12) . . ?
N4 N3 N2 105.92(11) . . ?
N3 N4 C1 105.72(12) . . ?
N1 C1 N4 113.00(12) . . ?
N1 C1 C1 123.13(15) . 2_665 ?
N4 C1 C1 123.87(16) . 2_665 ?
O1 C2 N2 110.56(12) . . ?
O1 C2 H2A 114.3(13) . . ?
N2 C2 H2A 109.3(13) . . ?
O1 C2 H2B 107.0(13) . . ?
N2 C2 H2B 110.3(14) . . ?
H2A C2 H2B 105.2(19) . . ?
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
O1 C2 1.4176(18) . ?
O1 N5 1.4327(16) . ?
O2 N5 1.1902(17) . ?
O3 N5 1.2043(17) . ?
N2 N1 1.3268(16) . ?
N2 N3 1.3269(17) . ?
N2 C2 1.4599(17) . ?
N1 C1 1.3271(18) . ?
N3 N4 1.3143(18) . ?
N4 C1 1.3563(18) . ?
C1 C1 1.454(3) 2_665 ?
C2 H2A 0.928(19) . ?
C2 H2B 0.91(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 -0.35(16) . . . . ?
C2 N2 N1 C1 -177.22(12) . . . . ?
C2 O1 N5 O2 3.57(18) . . . . ?
C2 O1 N5 O3 -176.33(12) . . . . ?
N1 N2 N3 N4 0.06(17) . . . . ?
C2 N2 N3 N4 176.96(12) . . . . ?
N2 N3 N4 C1 0.26(15) . . . . ?
N2 N1 C1 N4 0.52(15) . . . . ?
N2 N1 C1 C1 -178.89(7) . . . 2_665 ?
N3 N4 C1 N1 -0.52(15) . . . . ?
N3 N4 C1 C1 178.89(8) . . . 2_665 ?
N5 O1 C2 N2 -78.68(14) . . . . ?
N1 N2 C2 O1 -51.58(17) . . . . ?
N3 N2 C2 O1 131.79(14) . . . . ?
