#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:58:32 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/66/7236633.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_7236633
loop_
_publ_author_name
'Wang, Binshen'
'Qi, Xiujuan'
'Zhang, Wenquan'
'Wang, Kangcai'
'Li, Wei'
'Zhang, Qinghua'
_publ_section_title
;
 Synthesis of 1-(2H-tetrazol-5-yl)-5-nitraminotetrazole and its
 derivatives from 5-aminotetrazole and cyanogen azide: a promising
 strategy towards the development of C--N linked bistetrazolate energetic
 materials
;
_journal_issue                   39
_journal_name_full               'J. Mater. Chem. A'
_journal_page_first              20867
_journal_paper_doi               10.1039/C7TA05905A
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C8 H8 K4 N36'
_chemical_formula_sum            'C8 H8 K4 N36'
_chemical_formula_weight         764.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-13 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.904(14)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   7.767(3)
_cell_length_b                   11.993(4)
_cell_length_c                   7.360(3)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.012
_cell_measurement_theta_min      2.680
_cell_volume                     670.8(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8770
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.680
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0600 before and 0.0487 after correction. The Ratio of minimum to maximum transmission is 0.8919. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0339P)²+0.1517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1340
_reflns_number_total             1516
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ta05905a2.cif
_cod_data_source_block           mo_2016597_0m
_cod_database_code               7236633
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
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
K1 K 0.86409(4) 0.73879(2) 0.43818(4) 0.01940(11) Uani 1 1 d
N5 N 0.68095(15) 0.37443(9) 0.84942(17) 0.0166(3) Uani 1 1 d
N9 N 0.97543(16) 0.40264(10) 0.80418(18) 0.0186(3) Uani 1 1 d
N8 N 1.05507(16) 0.49267(10) 0.74767(18) 0.0201(3) Uani 1 1 d
N7 N 0.94497(16) 0.57584(10) 0.71334(18) 0.0199(3) Uani 1 1 d
N6 N 0.78685(16) 0.54454(10) 0.74701(18) 0.0197(3) Uani 1 1 d
N2 N 0.42871(16) 0.30713(10) 0.87937(19) 0.0219(3) Uani 1 1 d
N4 N 0.71242(18) 0.26966(10) 0.9255(2) 0.0233(3) Uani 1 1 d
N1 N 0.42969(18) 0.48914(11) 0.7493(2) 0.0265(3) Uani 1 1 d
N3 N 0.56107(18) 0.23257(11) 0.9415(2) 0.0256(3) Uani 1 1 d
C2 C 0.81358(18) 0.43940(11) 0.80094(19) 0.0150(3) Uani 1 1 d
C1 C 0.50641(19) 0.39586(12) 0.8222(2) 0.0179(3) Uani 1 1 d
H1A H 0.493(2) 0.5384(15) 0.713(2) 0.025(5) Uiso 1 1 d
H1B H 0.310(3) 0.4971(15) 0.739(3) 0.031(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'
K K 0.2009 0.2494 '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
K1 K1 K1 171.642(19) 4_575 4_576
N9 K1 K1 121.75(3) 2_756 4_575
N9 K1 K1 49.11(3) 3_766 4_575
N9 K1 K1 51.16(3) 2_756 4_576
N9 K1 K1 137.67(3) 3_766 4_576
N9 K1 N9 128.83(5) 2_756 3_766
N9 K1 N8 141.82(4) 2_756 3_766
N9 K1 N8 24.88(3) 3_766 3_766
N9 K1 N7 74.61(5) 2_756 4_575
N9 K1 N6 74.17(4) 2_756 4_575
N9 K1 N6 106.86(4) 3_766 4_575
N9 K1 N2 144.90(4) 2_756 3_666
N9 K1 N2 76.39(4) 3_766 3_666
N9 K1 N2 77.25(4) 2_756 2_656
N9 K1 N2 153.53(4) 3_766 2_656
N9 K1 N4 55.82(3) 2_756 2_756
N9 K1 N4 73.92(4) 3_766 2_756
N9 K1 C1 152.04(3) 2_756 3_666
N9 K1 C1 78.70(4) 3_766 3_666
N8 K1 K1 121.85(3) 3_766 4_576
N8 K1 K1 66.31(3) 3_766 4_575
N8 K1 N4 87.47(3) 3_766 2_756
N8 K1 C1 65.15(4) 3_766 3_666
N7 K1 K1 48.26(3) 4_575 4_575
N7 K1 K1 51.22(3) . 4_576
N7 K1 K1 136.75(3) . 4_575
N7 K1 K1 123.69(3) 4_575 4_576
N7 K1 N9 88.62(4) . 3_766
N7 K1 N9 85.82(4) 4_575 3_766
N7 K1 N9 89.88(5) . 2_756
N7 K1 N8 70.70(4) . 3_766
N7 K1 N8 109.46(4) 4_575 3_766
N7 K1 N7 154.54(5) . 4_575
N7 K1 N6 162.51(4) . 4_575
N7 K1 N6 26.67(3) 4_575 4_575
N7 K1 N2 86.80(4) . 2_656
N7 K1 N2 108.62(4) 4_575 2_656
N7 K1 N2 117.67(4) . 3_666
N7 K1 N2 85.07(4) 4_575 3_666
N7 K1 N4 76.47(4) 4_575 2_756
N7 K1 N4 78.12(4) . 2_756
N7 K1 C1 96.36(4) . 3_666
N7 K1 C1 106.83(4) 4_575 3_666
N6 K1 K1 60.21(3) 4_575 4_575
N6 K1 K1 111.64(3) 4_575 4_576
N6 K1 N8 126.50(4) 4_575 3_766
N6 K1 N2 74.94(4) 4_575 3_666
N6 K1 N2 82.77(4) 4_575 2_656
N6 K1 N4 98.02(4) 4_575 2_756
N6 K1 C1 94.68(4) 4_575 3_666
N2 K1 K1 51.94(3) 3_666 4_575
N2 K1 K1 125.84(3) 2_656 4_575
N2 K1 K1 51.28(3) 2_656 4_576
N2 K1 K1 130.06(3) 3_666 4_576
N2 K1 N8 131.51(3) 2_656 3_766
N2 K1 N8 71.86(4) 3_666 3_766
N2 K1 N2 82.74(5) 3_666 2_656
N2 K1 N4 130.18(4) 2_656 2_756
N2 K1 N4 145.90(4) 3_666 2_756
N2 K1 C1 75.92(4) 2_656 3_666
N2 K1 C1 21.76(3) 3_666 3_666
N4 K1 K1 83.81(3) 2_756 4_576
N4 K1 K1 95.24(3) 2_756 4_575
N4 K1 C1 152.14(3) 2_756 3_666
C1 K1 K1 114.21(3) 3_666 4_576
C1 K1 K1 69.95(3) 3_666 4_575
N4 N5 C2 122.35(12) . .
C1 N5 N4 108.77(11) . .
C1 N5 C2 128.74(12) . .
K1 N9 K1 79.73(4) 2_746 3_766
N8 N9 K1 126.40(9) . 2_746
N8 N9 K1 89.77(8) . 3_766
C2 N9 K1 121.75(9) . 2_746
C2 N9 K1 134.72(10) . 3_766
C2 N9 N8 102.76(11) . .
N9 N8 K1 65.35(7) . 3_766
N7 N8 K1 139.13(10) . 3_766
N7 N8 N9 110.31(11) . .
K1 N7 K1 80.52(4) . 4_576
N8 N7 K1 135.77(9) . .
N8 N7 K1 133.04(10) . 4_576
N8 N7 N6 109.60(11) . .
N6 N7 K1 104.47(9) . .
N6 N7 K1 78.35(8) . 4_576
N7 N6 K1 74.99(7) . 4_576
C2 N6 K1 133.61(10) . 4_576
C2 N6 N7 103.09(11) . .
K1 N2 K1 76.78(4) 3_666 2_646
N3 N2 K1 105.07(9) . 2_646
N3 N2 K1 123.00(9) . 3_666
C1 N2 K1 102.93(10) . 3_666
C1 N2 K1 142.89(9) . 2_646
C1 N2 N3 105.62(12) . .
N5 N4 K1 108.21(8) . 2_746
N3 N4 K1 144.84(10) . 2_746
N3 N4 N5 105.32(12) . .
C1 N1 H1A 118.1(12) . .
C1 N1 H1B 118.9(11) . .
H1A N1 H1B 123.0(17) . .
N4 N3 N2 112.44(12) . .
N9 C2 N5 123.79(13) . .
N6 C2 N5 121.98(12) . .
N6 C2 N9 114.24(12) . .
N5 C1 K1 132.65(9) . 3_666
N2 C1 K1 55.31(8) . 3_666
N2 C1 N5 107.85(12) . .
N1 C1 K1 85.29(10) . 3_666
N1 C1 N5 124.89(13) . .
N1 C1 N2 127.26(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 K1 3.6898(16) 4_575
K1 K1 3.6898(16) 4_576
K1 N9 2.8348(15) 2_756
K1 N9 2.9206(14) 3_766
K1 N8 3.2133(15) 3_766
K1 N7 2.7912(15) .
K1 N7 2.9163(14) 4_575
K1 N6 2.9571(15) 4_575
K1 N2 2.9571(16) 3_666
K1 N2 2.9844(14) 2_656
K1 N4 3.2560(18) 2_756
K1 C1 3.5052(18) 3_666
N5 N4 1.3767(17) .
N5 C2 1.3954(17) .
N5 C1 1.3536(19) .
N9 K1 2.8348(15) 2_746
N9 K1 2.9206(14) 3_766
N9 N8 1.3518(16) .
N9 C2 1.3277(18) .
N8 K1 3.2133(15) 3_766
N8 N7 1.3042(17) .
N7 K1 2.9162(14) 4_576
N7 N6 1.3550(17) .
N6 K1 2.9571(15) 4_576
N6 C2 1.3254(19) .
N2 K1 2.9843(14) 2_646
N2 K1 2.9571(16) 3_666
N2 N3 1.3680(19) .
N2 C1 1.3334(18) .
N4 K1 3.2560(18) 2_746
N4 N3 1.2849(19) .
N1 C1 1.328(2) .
N1 H1A 0.847(19) .
N1 H1B 0.918(19) .
C1 K1 3.5052(17) 3_666
