#------------------------------------------------------------------------------
#$Date: 2019-11-23 14:56:47 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/58/7235883.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_7235883
loop_
_publ_author_name
'Chen, Dong'
'Huang, Shiliang'
'Zhang, Qi'
'Yu, Qian'
'Zhou, Xiaoqing'
'Li, Hongzhen'
'Li, Jinshan'
_publ_section_title
;
 Two nitrogen-rich Ni(ii) coordination compounds based on
 5,5′-azotetrazole: synthesis, characterization and effect on
 thermal decomposition for RDX, HMX and AP
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              32872
_journal_paper_doi               10.1039/C5RA02464A
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C6 H24 N6 Ni, 2(C N5), C4 H8 O'
_chemical_formula_sum            'C12 H32 N16 Ni O'
_chemical_formula_weight         475.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_block_doi                 10.5517/cc142t23
_audit_creation_date             2015-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-02-01 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                103.658(7)
_cell_angle_beta                 109.217(5)
_cell_angle_gamma                99.019(7)
_cell_formula_units_Z            2
_cell_length_a                   9.439(5)
_cell_length_b                   10.414(4)
_cell_length_c                   12.275(5)
_cell_volume                     1070.4(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      140.15
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_measured_fraction_theta_max 0.9877
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6107
_diffrn_reflns_theta_full        26.3689
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.948
_exptl_crystal_density_diffrn    1.4743
_exptl_crystal_F_000             504.8132
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.8378
_refine_diff_density_min         -0.7679
_refine_diff_density_rms         0.1888
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             11.0256
_refine_ls_goodness_of_fit_ref   1.0649
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4322
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.0636
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.0153
_refine_ls_shift/su_mean         0.0011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1336P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1835
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -11
_reflns_limit_l_max              10
_reflns_limit_l_min              -15
_reflns_number_gt                3609
_reflns_number_total             4322
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ra02464a2.cif
_cod_data_source_block           dm1
_cod_database_code               7235883
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.640(5) 0.360(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
3. Restrained distances
 O1-C9 = O1-C12
 1.4 with sigma of 0.001
 C9-C10 = C10-C11 = C11-C12
 1.5 with sigma of 0.001
 O1'-C9' = O1'-C12'
 1.4 with sigma of 0.001
 C9'-C10' = C10'-C11' = C11'-C12'
 1.5 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(C9) = Uanis(C10) = Uanis(C11) = Uanis(C12) = Uanis(O1') =
Uanis(C9') = Uanis(C10') = Uanis(C11') = Uanis(C12')
5. Others
 Sof(O1')=Sof(C9')=Sof(H9'a)=Sof(H9'b)=Sof(C10')=Sof(H10c)=Sof(H10d)=Sof(C11')=
 Sof(H11c)=Sof(H11d)=Sof(C12')=Sof(H12c)=Sof(H12d)=1-FVAR(1)
 Sof(O1)=Sof(C9)=Sof(H9a)=Sof(H9b)=Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(C11)=
 Sof(H11a)=Sof(H11b)=Sof(C12)=Sof(H12a)=Sof(H12b)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 N1(H1a,H1b), N2(H2a,H2b), N3(H3a,H3b), N4(H4a,H4b), N5(H5a,H5b), N6(H6a,H6b),
 C1(H1c,H1d), C2(H2c,H2d), C3(H3c,H3d), C4(H4c,H4d), C5(H5c,H5d), C6(H6c,H6d),
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b), C12(H12a,H12b), C9'(H9'a,H9'b),
 C10'(H10c,H10d), C11'(H11c,H11d), C12'(H12c,H12d)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
_atom_site_disorder_group
Ni1 Ni 0.88181(5) 0.24511(4) 0.18129(4) 0.01708(19) Uani 1.000000 . .
N1 N 0.7681(4) 0.1173(4) 0.2561(3) 0.0253(7) Uani 1.000000 . .
H1a H 0.7388(4) 0.0277(4) 0.2083(3) 0.0304(9) Uiso 1.000000 R .
H1b H 0.8336(4) 0.1236(4) 0.3327(3) 0.0304(9) Uiso 1.000000 R .
N2 N 0.7379(4) 0.3698(4) 0.2247(3) 0.0271(8) Uani 1.000000 . .
H2a H 0.7949(4) 0.4592(4) 0.2629(3) 0.0326(9) Uiso 1.000000 R .
H2b H 0.6587(4) 0.3662(4) 0.1551(3) 0.0326(9) Uiso 1.000000 R .
N3 N 0.7176(4) 0.1408(3) 0.0038(3) 0.0247(7) Uani 1.000000 . .
H3a H 0.6960(4) 0.0479(3) -0.0091(3) 0.0297(9) Uiso 1.000000 R .
H3b H 0.6268(4) 0.1676(3) -0.0078(3) 0.0297(9) Uiso 1.000000 R .
N4 N 0.9602(4) 0.3756(3) 0.0918(3) 0.0244(7) Uani 1.000000 . .
H4a H 0.9639(4) 0.4645(3) 0.1288(3) 0.0293(9) Uiso 1.000000 R .
H4b H 1.0585(4) 0.3713(3) 0.0963(3) 0.0293(9) Uiso 1.000000 R .
N5 N 1.0320(4) 0.1150(3) 0.1646(3) 0.0240(7) Uani 1.000000 . .
H5a H 0.9794(4) 0.0253(3) 0.1449(3) 0.0288(9) Uiso 1.000000 R .
H5b H 1.0663(4) 0.1239(3) 0.1041(3) 0.0288(9) Uiso 1.000000 R .
N6 N 1.0699(4) 0.3497(3) 0.3474(3) 0.0267(8) Uani 1.000000 . .
H6a H 1.0848(4) 0.4426(3) 0.3627(3) 0.0321(9) Uiso 1.000000 R .
H6b H 1.0507(4) 0.3268(3) 0.4101(3) 0.0321(9) Uiso 1.000000 R .
N7 N 0.0106(4) 0.0150(3) 0.5553(3) 0.0225(7) Uani 1.000000 . .
N8 N -0.0201(4) 0.2423(3) 0.5449(3) 0.0267(8) Uani 1.000000 . .
N9 N -0.0135(5) 0.3534(4) 0.6304(3) 0.0304(8) Uani 1.000000 . .
N10 N 0.0120(5) 0.3266(3) 0.7338(3) 0.0318(8) Uani 1.000000 . .
N11 N 0.0218(5) 0.1966(3) 0.7183(3) 0.0314(8) Uani 1.000000 . .
N12 N 0.4349(4) 0.4940(3) 0.0041(3) 0.0200(7) Uani 1.000000 . .
N13 N 0.4191(4) 0.2488(3) -0.0288(3) 0.0256(8) Uani 1.000000 . .
N14 N 0.3178(4) 0.1504(3) -0.0185(4) 0.0264(8) Uani 1.000000 . .
N15 N 0.2168(4) 0.2033(3) 0.0184(3) 0.0261(8) Uani 1.000000 . .
N16 N 0.2464(4) 0.3369(3) 0.0299(3) 0.0253(8) Uani 1.000000 . .
C1 C 0.6307(5) 0.1646(5) 0.2611(4) 0.0312(10) Uani 1.000000 . .
H1c H 0.5467(5) 0.1310(5) 0.1794(4) 0.0374(12) Uiso 1.000000 R .
H1d H 0.5926(5) 0.1280(5) 0.3166(4) 0.0374(12) Uiso 1.000000 R .
C2 C 0.6734(6) 0.3187(5) 0.3055(5) 0.0330(10) Uani 1.000000 . .
H2c H 0.7513(6) 0.3524(5) 0.3897(5) 0.0395(12) Uiso 1.000000 R .
H2d H 0.5804(6) 0.3518(5) 0.3046(5) 0.0395(12) Uiso 1.000000 R .
C3 C 0.7879(5) 0.1767(4) -0.0798(4) 0.0238(8) Uani 1.000000 . .
H3c H 0.8720(5) 0.1306(4) -0.0798(4) 0.0286(10) Uiso 1.000000 R .
H3d H 0.7086(5) 0.1469(4) -0.1634(4) 0.0286(10) Uiso 1.000000 R .
C4 C 0.8528(5) 0.3316(4) -0.0361(4) 0.0250(9) Uani 1.000000 . .
H4c H 0.7667(5) 0.3768(4) -0.0443(4) 0.0300(10) Uiso 1.000000 R .
H4d H 0.9082(5) 0.3583(4) -0.0864(4) 0.0300(10) Uiso 1.000000 R .
C5 C 1.1651(5) 0.1543(4) 0.2814(4) 0.0269(9) Uani 1.000000 . .
H5c H 1.1368(5) 0.1103(4) 0.3371(4) 0.0323(11) Uiso 1.000000 R .
H5d H 1.2540(5) 0.1237(4) 0.2684(4) 0.0323(11) Uiso 1.000000 R .
C6 C 1.2095(5) 0.3082(4) 0.3363(4) 0.0283(9) Uani 1.000000 . .
H6c H 1.2454(5) 0.3525(4) 0.2837(4) 0.0339(11) Uiso 1.000000 R .
H6d H 1.2946(5) 0.3363(4) 0.4171(4) 0.0339(11) Uiso 1.000000 R .
C7 C 0.0035(5) 0.1505(4) 0.6028(4) 0.0218(8) Uani 1.000000 . .
C8 C 0.3708(4) 0.3610(4) 0.0025(4) 0.0204(8) Uani 1.000000 . .
O1 O 0.4844(6) 0.4000(5) 0.6359(5) 0.0563(8) Uani 0.731(6) D 1
C9 C 0.6078(8) 0.3433(7) 0.6304(9) 0.0563(8) Uani 0.731(6) D 1
H9a H 0.6532(8) 0.3788(7) 0.5779(9) 0.0675(10) Uiso 0.731(6) R 1
H9b H 0.6897(8) 0.3695(7) 0.7126(9) 0.0675(10) Uiso 0.731(6) R 1
C10 C 0.5507(9) 0.1906(7) 0.5804(9) 0.0563(8) Uani 0.731(6) D 1
H10a H 0.5119(9) 0.1588(7) 0.4907(9) 0.0675(10) Uiso 0.731(6) R 1
H10b H 0.6322(9) 0.1453(7) 0.6138(9) 0.0675(10) Uiso 0.731(6) R 1
C11 C 0.4216(9) 0.1672(7) 0.6249(8) 0.0563(8) Uani 0.731(6) D 1
H11a H 0.3223(9) 0.1153(7) 0.5569(8) 0.0675(10) Uiso 0.731(6) R 1
H11b H 0.4452(9) 0.1168(7) 0.6850(8) 0.0675(10) Uiso 0.731(6) R 1
C12 C 0.4148(10) 0.3090(6) 0.6823(7) 0.0563(8) Uani 0.731(6) D 1
H12a H 0.4698(10) 0.3357(6) 0.7714(7) 0.0675(10) Uiso 0.731(6) R 1
H12b H 0.3054(10) 0.3120(6) 0.6647(7) 0.0675(10) Uiso 0.731(6) R 1
O1' O 0.5034(15) 0.1161(13) 0.6362(13) 0.0563(8) Uani 0.269(6) D 2
C9' C 0.4115(19) 0.2030(14) 0.662(2) 0.0563(8) Uani 0.269(6) D 2
H9'a H 0.3111(19) 0.1790(14) 0.592(2) 0.0675(10) Uiso 0.269(6) R 2
H9'b H 0.3908(19) 0.1953(14) 0.734(2) 0.0675(10) Uiso 0.269(6) R 2
C10' C 0.502(2) 0.3452(16) 0.6844(18) 0.0563(8) Uani 0.269(6) D 2
H10c H 0.429(2) 0.4029(16) 0.6647(18) 0.0675(10) Uiso 0.269(6) R 2
H10d H 0.570(2) 0.3850(16) 0.7714(18) 0.0675(10) Uiso 0.269(6) R 2
C11' C 0.598(2) 0.3455(17) 0.609(2) 0.0563(8) Uani 0.269(6) D 2
H11c H 0.549(2) 0.3664(17) 0.533(2) 0.0675(10) Uiso 0.269(6) R 2
H11d H 0.705(2) 0.4046(17) 0.655(2) 0.0675(10) Uiso 0.269(6) R 2
C12' C 0.589(2) 0.1963(16) 0.591(2) 0.0563(8) Uani 0.269(6) D 2
H12c H 0.697(2) 0.1884(16) 0.624(2) 0.0675(10) Uiso 0.269(6) R 2
H12d H 0.548(2) 0.1514(16) 0.502(2) 0.0675(10) Uiso 0.269(6) R 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 Ni1 N1 81.87(13)
N3 Ni1 N1 91.87(14)
N3 Ni1 N2 93.56(14)
N4 Ni1 N1 171.06(13)
N4 Ni1 N2 91.82(13)
N4 Ni1 N3 82.16(13)
N5 Ni1 N1 91.40(13)
N5 Ni1 N2 171.01(14)
N5 Ni1 N3 92.61(13)
N5 Ni1 N4 95.50(13)
N6 Ni1 N1 94.34(14)
N6 Ni1 N2 92.59(14)
N6 Ni1 N3 171.82(13)
N6 Ni1 N4 92.26(14)
N6 Ni1 N5 81.93(13)
C1 N1 Ni1 107.3(3)
C2 N2 Ni1 108.3(3)
C3 N3 Ni1 106.5(2)
C4 N4 Ni1 109.0(2)
C5 N5 Ni1 108.6(2)
C6 N6 Ni1 107.1(2)
C7 N8 N9 103.9(3)
N10 N9 N8 109.7(3)
N11 N10 N9 109.3(3)
C7 N11 N10 104.0(3)
C8 N13 N14 103.3(3)
N15 N14 N13 110.0(3)
N16 N15 N14 109.2(3)
C8 N16 N15 104.4(3)
C2 C1 N1 109.3(4)
C1 C2 N2 108.4(4)
C4 C3 N3 107.7(3)
C3 C4 N4 109.5(3)
C6 C5 N5 108.9(3)
C5 C6 N6 107.8(3)
N8 C7 N7 127.6(4)
N11 C7 N7 119.3(4)
N11 C7 N8 113.2(4)
N13 C8 N12 126.8(3)
N16 C8 N12 120.1(3)
N16 C8 N13 113.1(3)
C12 O1 C9 98.8(6)
C10 C9 O1 109.6(6)
C11 C10 C9 100.4(6)
C12 C11 C10 103.6(6)
C11 C12 O1 109.2(6)
C12' O1' C9' 98.9(15)
C10' C9' O1' 106.4(14)
C11' C10' C9' 111.1(16)
C12' C11' C10' 91.1(15)
C11' C12' O1' 123.4(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.132(3) .
Ni1 N2 2.126(3) .
Ni1 N3 2.112(3) .
Ni1 N4 2.127(3) .
Ni1 N5 2.133(3) .
Ni1 N6 2.111(4) .
N1 C1 1.471(5) .
N2 C2 1.477(6) .
N3 C3 1.478(5) .
N4 C4 1.473(5) .
N5 C5 1.476(5) .
N6 C6 1.487(5) .
N7 N7 1.258(7) 2_556
N7 C7 1.415(5) .
N8 N9 1.343(5) .
N8 C7 1.323(5) .
N9 N10 1.316(5) .
N10 N11 1.344(5) .
N11 C7 1.327(5) .
N12 N12 1.255(6) 2_665
N12 C8 1.415(5) .
N13 N14 1.346(5) .
N13 C8 1.338(5) .
N14 N15 1.323(5) .
N15 N16 1.339(5) .
N16 C8 1.328(5) .
C1 C2 1.508(6) .
C3 C4 1.527(5) .
C5 C6 1.513(6) .
O1 C9 1.4000(12) .
O1 C12 1.4001(11) .
C9 C10 1.4998(11) .
C10 C11 1.5003(12) .
C11 C12 1.5001(11) .
O1' C9' 1.4001(11) .
O1' C12' 1.4001(11) .
C9' C10' 1.5000(11) .
C10' C11' 1.5000(11) .
C11' C12' 1.5000(12) .
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O1 C9 1 1.4000 0.0010 0.0000
O1 C12 1 1.4000 0.0010 -0.0001
C9 C10 1 1.5000 0.0010 0.0002
C10 C11 1 1.5000 0.0010 -0.0003
C11 C12 1 1.5000 0.0010 -0.0001
O1' C9' 1 1.4000 0.0010 -0.0001
O1' C12' 1 1.4000 0.0010 -0.0001
C9' C10' 1 1.5000 0.0010 -0.0000
C10' C11' 1 1.5000 0.0010 0.0000
C11' C12' 1 1.5000 0.0010 0.0000
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.640(5)
2 0.360(5)
