#------------------------------------------------------------------------------
#$Date: 2021-09-30 02:11:58 +0300 (Thu, 30 Sep 2021) $
#$Revision: 269383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/84/7708471.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_7708471
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 Cl2 N8'
_chemical_formula_sum            'C4 H4 Cl2 N8'
_chemical_formula_weight         235.05
_chemical_name_common            2,2-chloromethyl-5,5-bitetrazole
_chemical_name_systematic        2,2-chloromethyl-5,5-bitetrazole
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-07-10
_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                 108.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3693(4)
_cell_length_b                   8.2279(4)
_cell_length_c                   6.7862(3)
_cell_measurement_reflns_used    7117
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      30.5317
_cell_measurement_theta_min      3.5634
_cell_volume                     443.95(4)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Microsoft Word 2016'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      105(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11605
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         3.563
_diffrn_source                   'rotating anode generator'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         1355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0273
_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)+(0.0205P)²+0.3218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1190
_reflns_number_total             1355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02731j2.cif
_cod_data_source_block           yv377
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7708471
_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   0.933
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-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
Cl1 Cl 0.14858(4) 0.33191(4) 0.93683(5) 0.02309(10) Uani 1 1 d . . . . .
N2 N 0.26922(13) 0.53424(14) 0.71052(16) 0.0161(2) Uani 1 1 d . . . . .
N4 N 0.28055(14) 0.57776(15) 0.40842(17) 0.0197(2) Uani 1 1 d . . . . .
N3 N 0.18054(14) 0.58798(14) 0.52389(17) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.42443(14) 0.48718(14) 0.72558(17) 0.0183(2) Uani 1 1 d . . . . .
C1 C 0.42701(15) 0.51578(16) 0.53388(19) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.20209(17) 0.53198(16) 0.8830(2) 0.0180(2) Uani 1 1 d . . . . .
H2A H 0.287(2) 0.572(2) 1.000(3) 0.026(4) Uiso 1 1 d . . . . .
H2B H 0.105(2) 0.594(2) 0.846(3) 0.026(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'
Cl Cl 0.1484 0.1585 '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
N3 N2 N1 114.35(10) . . ?
N3 N2 C2 122.20(11) . . ?
N1 N2 C2 123.43(11) . . ?
N3 N4 C1 105.59(10) . . ?
N4 N3 N2 106.07(10) . . ?
N2 N1 C1 100.80(10) . . ?
N1 C1 N4 113.19(11) . . ?
N1 C1 C1 123.30(14) . 3_666 ?
N4 C1 C1 123.51(14) . 3_666 ?
N2 C2 Cl1 111.40(9) . . ?
N2 C2 H2A 107.1(11) . . ?
Cl1 C2 H2A 108.7(11) . . ?
N2 C2 H2B 107.7(12) . . ?
Cl1 C2 H2B 108.1(12) . . ?
H2A C2 H2B 113.8(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
Cl1 C2 1.7737(14) . ?
N2 N3 1.3279(15) . ?
N2 N1 1.3285(15) . ?
N2 C2 1.4482(15) . ?
N4 N3 1.3157(15) . ?
N4 C1 1.3549(17) . ?
N1 C1 1.3288(15) . ?
C1 C1 1.457(2) 3_666 ?
C2 H2A 0.95(2) . ?
C2 H2B 0.92(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
C1 N4 N3 N2 0.49(14) . . . . ?
N1 N2 N3 N4 -0.42(15) . . . . ?
C2 N2 N3 N4 178.01(11) . . . . ?
N3 N2 N1 C1 0.14(14) . . . . ?
C2 N2 N1 C1 -178.26(12) . . . . ?
N2 N1 C1 N4 0.20(14) . . . . ?
N2 N1 C1 C1 179.94(16) . . . 3_666 ?
N3 N4 C1 N1 -0.45(15) . . . . ?
N3 N4 C1 C1 179.80(16) . . . 3_666 ?
N3 N2 C2 Cl1 105.39(12) . . . . ?
N1 N2 C2 Cl1 -76.33(14) . . . . ?
