#------------------------------------------------------------------------------
#$Date: 2019-11-23 15:35:18 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/93/4349320.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_4349320
loop_
_publ_author_name
'Seth, Saona'
'Matzger, Adam J.'
_publ_section_title
;
 Coordination Polymerization of 5,5'-Dinitro-2H,2H'-3,3'-bi-1,2,4-triazole
 Leads to a Dense Explosive with High Thermal Stability.
;
_journal_issue                   1
_journal_name_full               'Inorganic chemistry'
_journal_page_first              561
_journal_page_last               565
_journal_paper_doi               10.1021/acs.inorgchem.6b02383
_journal_volume                  56
_journal_year                    2017
_chemical_formula_moiety         'C8 H4 N16 Ni O10, 2(C2 H8 N), 2(H2 O)'
_chemical_formula_sum            'C12 H24 N18 Ni O12'
_chemical_formula_weight         671.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                99.422(7)
_cell_angle_beta                 91.316(6)
_cell_angle_gamma                102.579(7)
_cell_formula_units_Z            1
_cell_length_a                   6.9323(5)
_cell_length_b                   7.5416(5)
_cell_length_c                   12.9399(11)
_cell_measurement_reflns_used    3094
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.9700
_cell_measurement_theta_min      3.4810
_cell_volume                     650.15(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1719
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.121
_diffrn_reflns_theta_min         3.469
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    1.941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_description       plate
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4177
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0721
_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)+(0.1325P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1781
_refine_ls_wR_factor_ref         0.1847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2883
_reflns_number_total             4177
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b02383_si_001.cif
_cod_data_source_block           Ni-DNBT
_cod_database_code               4349320
_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   0.698
_shelx_estimated_absorpt_t_max   0.698
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Ni1 Ni 0.5000 1.0000 0.5000 0.0151(4) Uani 1 2 d S . P
O1 O 0.1420(5) 0.7998(5) 0.8880(3) 0.0242(9) Uani 1 1 d . . .
O2 O -0.0055(5) 0.5190(5) 0.8166(3) 0.0227(9) Uani 1 1 d . . .
O3 O 0.4833(5) 0.3875(5) 0.1508(3) 0.0223(8) Uani 1 1 d . . .
O4 O 0.2732(5) 0.1835(5) 0.2170(3) 0.0235(9) Uani 1 1 d . . .
O5 O 0.7574(5) 0.9271(5) 0.5454(3) 0.0185(8) Uani 1 1 d D . .
H5A H 0.733(10) 0.827(7) 0.572(5) 0.05(2) Uiso 1 1 d D . .
H5B H 0.842(9) 1.015(8) 0.584(5) 0.06(2) Uiso 1 1 d D . .
O6 O 1.0626(6) 1.1774(5) 0.6510(3) 0.0211(8) Uani 1 1 d D . .
H6A H 1.142(9) 1.152(10) 0.603(5) 0.06(2) Uiso 1 1 d D . .
H6B H 1.072(12) 1.294(6) 0.651(6) 0.07(3) Uiso 1 1 d D . .
N1 N 0.3364(6) 0.8431(5) 0.6025(3) 0.0151(9) Uani 1 1 d . . .
N2 N 0.2802(6) 0.8691(6) 0.7033(3) 0.0166(9) Uani 1 1 d . . .
N3 N 0.1719(6) 0.5659(5) 0.6322(3) 0.0165(9) Uani 1 1 d . . .
N4 N 0.1014(6) 0.6717(6) 0.8136(3) 0.0192(10) Uani 1 1 d . . .
N5 N 0.4182(6) 0.7355(5) 0.4087(3) 0.0156(9) Uani 1 1 d . . .
N6 N 0.4541(6) 0.6520(6) 0.3123(3) 0.0165(9) Uani 1 1 d . . .
N7 N 0.2868(6) 0.4331(5) 0.3998(3) 0.0158(9) Uani 1 1 d . . .
N8 N 0.3763(6) 0.3396(6) 0.2208(3) 0.0192(9) Uani 1 1 d . . .
N9 N 0.3346(7) 1.1983(7) 0.8532(4) 0.0206(10) Uani 1 1 d . . .
H9A H 0.363(10) 1.270(10) 0.806(6) 0.05(2) Uiso 1 1 d . . .
H9B H 0.298(9) 1.110(9) 0.817(5) 0.03(2) Uiso 1 1 d . . .
C1 C 0.1852(7) 0.7018(7) 0.7148(4) 0.0156(10) Uani 1 1 d . . .
C2 C 0.2695(7) 0.6622(7) 0.5646(4) 0.0154(10) Uani 1 1 d . . .
C3 C 0.3194(7) 0.6022(7) 0.4572(4) 0.0159(10) Uani 1 1 d . . .
C4 C 0.3731(7) 0.4758(7) 0.3126(4) 0.0156(10) Uani 1 1 d . . .
C5 C 0.1772(9) 1.2330(8) 0.9248(4) 0.0276(13) Uani 1 1 d . . .
H5E H 0.1613 1.1463 0.9744 0.041 Uiso 1 1 calc R U .
H5C H 0.0521 1.2159 0.8837 0.041 Uiso 1 1 calc R U .
H5D H 0.2146 1.3596 0.9636 0.041 Uiso 1 1 calc R U .
C6 C 0.5252(8) 1.1979(8) 0.9064(4) 0.0285(13) Uani 1 1 d . . .
H6E H 0.5780 1.3187 0.9501 0.043 Uiso 1 1 calc R U .
H6C H 0.6194 1.1722 0.8537 0.043 Uiso 1 1 calc R U .
H6D H 0.5048 1.1024 0.9506 0.043 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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
O5 Ni1 O5 180.0 . 2_676
O5 Ni1 N5 93.15(15) . 2_676
O5 Ni1 N5 86.85(15) 2_676 2_676
O5 Ni1 N5 86.85(15) . .
O5 Ni1 N5 93.15(15) 2_676 .
N5 Ni1 N5 180.0 2_676 .
O5 Ni1 N1 89.03(15) . 2_676
O5 Ni1 N1 90.97(15) 2_676 2_676
N5 Ni1 N1 77.08(15) 2_676 2_676
N5 Ni1 N1 102.92(15) . 2_676
O5 Ni1 N1 90.97(15) . .
O5 Ni1 N1 89.03(15) 2_676 .
N5 Ni1 N1 102.92(15) 2_676 .
N5 Ni1 N1 77.08(15) . .
N1 Ni1 N1 180.0(3) 2_676 .
Ni1 O5 H5A 112(5) . .
Ni1 O5 H5B 114(5) . .
H5A O5 H5B 113(7) . .
H6A O6 H6B 101(7) . .
C2 N1 N2 106.0(4) . .
C2 N1 Ni1 115.8(3) . .
N2 N1 Ni1 138.1(3) . .
C1 N2 N1 103.1(4) . .
C2 N3 C1 99.3(4) . .
O1 N4 O2 124.9(4) . .
O1 N4 C1 117.6(4) . .
O2 N4 C1 117.5(4) . .
C3 N5 N6 106.7(4) . .
C3 N5 Ni1 116.0(3) . .
N6 N5 Ni1 137.0(3) . .
C4 N6 N5 102.8(4) . .
C3 N7 C4 99.1(4) . .
O4 N8 O3 124.1(4) . .
O4 N8 C4 118.3(4) . .
O3 N8 C4 117.6(4) . .
C6 N9 C5 114.8(4) . .
C6 N9 H9A 106(5) . .
C5 N9 H9A 117(5) . .
C6 N9 H9B 110(5) . .
C5 N9 H9B 109(5) . .
H9A N9 H9B 98(6) . .
N2 C1 N3 117.2(4) . .
N2 C1 N4 120.0(4) . .
N3 C1 N4 122.8(4) . .
N2 C1 C2 77.0(3) . .
N3 C1 C2 40.2(3) . .
N4 C1 C2 163.0(4) . .
N3 C2 N1 114.4(4) . .
N3 C2 C3 130.4(5) . .
N1 C2 C3 115.2(4) . .
N3 C2 C1 40.5(3) . .
N1 C2 C1 73.9(3) . .
C3 C2 C1 170.8(4) . .
N7 C3 N5 114.1(4) . .
N7 C3 C2 130.0(4) . .
N5 C3 C2 115.8(4) . .
N7 C3 C4 40.6(3) . .
N5 C3 C4 73.5(3) . .
C2 C3 C4 170.6(4) . .
N6 C4 N7 117.3(4) . .
N6 C4 N8 120.0(4) . .
N7 C4 N8 122.7(4) . .
N6 C4 C3 76.9(3) . .
N7 C4 C3 40.4(3) . .
N8 C4 C3 163.0(4) . .
N9 C5 H5E 109.5 . .
N9 C5 H5C 109.5 . .
H5E C5 H5C 109.5 . .
N9 C5 H5D 109.5 . .
H5E C5 H5D 109.5 . .
H5C C5 H5D 109.5 . .
N9 C6 H6E 109.5 . .
N9 C6 H6C 109.5 . .
H6E C6 H6C 109.5 . .
N9 C6 H6D 109.5 . .
H6E C6 H6D 109.5 . .
H6C C6 H6D 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O5 2.078(4) .
Ni1 O5 2.078(4) 2_676
Ni1 N5 2.097(4) 2_676
Ni1 N5 2.097(4) .
Ni1 N1 2.108(4) 2_676
Ni1 N1 2.108(4) .
O1 N4 1.227(5) .
O2 N4 1.234(5) .
O3 N8 1.233(5) .
O4 N8 1.229(5) .
O5 H5A 0.86(4) .
O5 H5B 0.86(4) .
O6 H6A 0.87(4) .
O6 H6B 0.87(4) .
N1 C2 1.346(6) .
N1 N2 1.365(6) .
N2 C1 1.324(6) .
N3 C2 1.331(6) .
N3 C1 1.341(6) .
N4 C1 1.447(6) .
N5 C3 1.341(6) .
N5 N6 1.357(6) .
N6 C4 1.326(6) .
N7 C3 1.336(6) .
N7 C4 1.343(6) .
N8 C4 1.442(7) .
N9 C6 1.477(7) .
N9 C5 1.486(7) .
N9 H9A 0.88(8) .
N9 H9B 0.74(7) .
C1 C2 2.037(7) .
C2 C3 1.463(7) .
C3 C4 2.038(7) .
C5 H5E 0.9800 .
C5 H5C 0.9800 .
C5 H5D 0.9800 .
C6 H6E 0.9800 .
C6 H6C 0.9800 .
C6 H6D 0.9800 .
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
O5 H5A N7 0.86(4) 2.03(4) 2.873(5) 164(7) 2_666
O5 H5B O6 0.86(4) 1.83(4) 2.681(5) 167(7) .
O6 H6A O5 0.87(4) 2.09(4) 2.925(5) 160(7) 2_776
N9 H9A O3 0.88(8) 2.53(7) 3.114(6) 124(6) 2_676
N9 H9A N6 0.88(8) 2.08(8) 2.867(6) 148(7) 2_676
N9 H9B N2 0.74(7) 2.12(7) 2.837(6) 164(7) .
C5 H5E O1 0.98 2.64 3.177(7) 114.6 .
O6 H6B O2 0.87(4) 2.65(7) 3.197(5) 122(6) 1_665
O6 H6B N3 0.87(4) 2.07(4) 2.914(5) 164(8) 1_665
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
C2 N1 N2 C1 -0.2(5)
Ni1 N1 N2 C1 -177.1(4)
C3 N5 N6 C4 -0.1(5)
Ni1 N5 N6 C4 172.2(4)
N1 N2 C1 N3 0.0(5)
N1 N2 C1 N4 179.9(4)
N1 N2 C1 C2 0.2(3)
C2 N3 C1 N2 0.2(5)
C2 N3 C1 N4 -179.7(4)
O1 N4 C1 N2 -8.5(7)
O2 N4 C1 N2 171.5(4)
O1 N4 C1 N3 171.4(4)
O2 N4 C1 N3 -8.5(7)
O1 N4 C1 C2 170.8(11)
O2 N4 C1 C2 -9.2(15)
C1 N3 C2 N1 -0.4(5)
C1 N3 C2 C3 178.0(5)
N2 N1 C2 N3 0.4(6)
Ni1 N1 C2 N3 178.1(3)
N2 N1 C2 C3 -178.2(4)
Ni1 N1 C2 C3 -0.5(5)
N2 N1 C2 C1 0.2(3)
Ni1 N1 C2 C1 177.9(3)
C4 N7 C3 N5 -0.3(5)
C4 N7 C3 C2 -178.2(5)
N6 N5 C3 N7 0.3(5)
Ni1 N5 C3 N7 -173.9(3)
N6 N5 C3 C2 178.5(4)
Ni1 N5 C3 C2 4.3(5)
N6 N5 C3 C4 0.1(3)
Ni1 N5 C3 C4 -174.1(3)
N3 C2 C3 N7 -3.0(9)
N1 C2 C3 N7 175.3(5)
N3 C2 C3 N5 179.1(5)
N1 C2 C3 N5 -2.5(6)
N5 N6 C4 N7 -0.1(6)
N5 N6 C4 N8 178.5(4)
N5 N6 C4 C3 0.1(3)
C3 N7 C4 N6 0.3(5)
C3 N7 C4 N8 -178.3(4)
O4 N8 C4 N6 -168.4(4)
O3 N8 C4 N6 11.8(7)
O4 N8 C4 N7 10.2(7)
O3 N8 C4 N7 -169.6(4)
O4 N8 C4 C3 6.5(15)
O3 N8 C4 C3 -173.3(11)
