# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dm1
_audit_block_doi                 10.5517/cc142t23
_database_code_depnum_ccdc_archive 'CCDC 1045384'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;
_audit_creation_date             2015-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_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
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.439(5)
_cell_length_b                   10.414(4)
_cell_length_c                   12.275(5)
_cell_angle_alpha                103.658(7)
_cell_angle_beta                 109.217(5)
_cell_angle_gamma                99.019(7)
_cell_volume                     1070.4(8)
_cell_formula_units_Z            2
_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
_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
_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
_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)
_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)'
_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_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.0636
_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
_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)
;
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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_
_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
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) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
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)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1045385'
_audit_update_record             
;
2015-01-25 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H20 N14 Ni'
_chemical_formula_sum            'C8 H20 N14 Ni'
_chemical_formula_weight         371.09

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ' Triclinic'
_symmetry_space_group_name_H-M   ' P -1 '
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7483(8)
_cell_length_b                   8.2141(9)
_cell_length_c                   8.2854(9)
_cell_angle_alpha                113.252(10)
_cell_angle_beta                 112.492(11)
_cell_angle_gamma                97.526(10)
_cell_volume                     367.73(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1152
_cell_measurement_theta_min      4.1790
_cell_measurement_theta_max      25.6030

_exptl_crystal_description       Plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             194
_exptl_absorpt_coefficient_mu    1.346
_exptl_absorpt_correction_T_min  0.83955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_method       'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2720
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0806
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1508
_reflns_number_gt                1292
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1508
_refine_ls_number_parameters     106
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1870
_refine_ls_wR_factor_gt          0.1503
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.5000 0.02357(18) Uani 1 2 d S . .
N1 N 0.6891(5) 0.5410(4) 0.3560(4) 0.0279(7) Uani 1 1 d . . .
H1A H 0.6493 0.6260 0.3188 0.033 Uiso 1 1 calc R . .
H1B H 0.8363 0.5957 0.4500 0.033 Uiso 1 1 calc R . .
N2 N 0.2521(5) 0.2543(4) 0.2321(4) 0.0305(8) Uani 1 1 d . . .
H2A H 0.1970 0.1763 0.2681 0.037 Uiso 1 1 calc R . .
H2B H 0.1366 0.2888 0.1718 0.037 Uiso 1 1 calc R . .
N5 N 0.6811(5) 0.3276(4) 0.5901(4) 0.0265(7) Uani 1 1 d . . .
N6 N 0.7964(5) 0.2364(4) 0.5087(4) 0.0272(7) Uani 1 1 d . . .
N7 N 0.7677(6) 0.1513(5) 0.7239(5) 0.0458(8) Uani 1 1 d U . .
N8 N 0.6649(6) 0.2779(5) 0.7198(5) 0.0440(8) Uani 1 1 d U . .
N9 N 0.9599(5) -0.0012(4) 0.5576(4) 0.0270(7) Uani 1 1 d . . .
C1 C 0.6782(2) 0.3842(4) 0.1804(4) 0.0314(9) Uani 1 1 d D . .
H3A H 0.7587 0.3070 0.2229 0.038 Uiso 1 1 calc R . .
H3B H 0.7527 0.4345 0.1225 0.038 Uiso 1 1 calc R . .
C2 C 0.4338(2) 0.2639(3) 0.0236(3) 0.0351(10) Uani 1 1 d D . .
H4A H 0.3490 0.3455 -0.0018 0.042 Uiso 1 1 calc R . .
H4B H 0.4320 0.1826 -0.0998 0.042 Uiso 1 1 calc R . .
C3 C 0.3129(5) 0.1430(4) 0.0795(5) 0.0359(10) Uani 1 1 d D . .
H5A H 0.1758 0.0482 -0.0393 0.043 Uiso 1 1 calc R . .
H5B H 0.4107 0.0790 0.1301 0.043 Uiso 1 1 calc R . .
C7 C 0.8455(6) 0.1304(5) 0.5947(5) 0.0254(8) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Ni1 N2 2.130(3) . ?
Ni1 N2 2.130(3) 2_666 ?
Ni1 N1 2.130(3) . ?
Ni1 N1 2.130(3) 2_666 ?
Ni1 N5 2.155(3) . ?
Ni1 N5 2.155(3) 2_666 ?
N1 C1 1.481(4) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C3 1.479(5) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N5 N8 1.326(5) . ?
N5 N6 1.333(4) . ?
N6 C7 1.328(5) . ?
N7 C7 1.326(5) . ?
N7 N8 1.327(5) . ?
N9 N9 1.270(7) 2_756 ?
N9 C7 1.413(5) . ?
C1 C2 1.5180(10) . ?
C1 H3A 0.9700 . ?
C1 H3B 0.9700 . ?
C2 C3 1.5180(10) . ?
C2 H4A 0.9700 . ?
C2 H4B 0.9700 . ?
C3 H5A 0.9700 . ?
C3 H5B 0.9700 . ?

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
N2 Ni1 N2 180.000(1) . 2_666 ?
N2 Ni1 N1 91.15(12) . . ?
N2 Ni1 N1 88.85(12) 2_666 . ?
N2 Ni1 N1 88.85(12) . 2_666 ?
N2 Ni1 N1 91.15(12) 2_666 2_666 ?
N1 Ni1 N1 180.000(1) . 2_666 ?
N2 Ni1 N5 89.52(12) . . ?
N2 Ni1 N5 90.48(12) 2_666 . ?
N1 Ni1 N5 92.47(12) . . ?
N1 Ni1 N5 87.53(12) 2_666 . ?
N2 Ni1 N5 90.48(12) . 2_666 ?
N2 Ni1 N5 89.52(12) 2_666 2_666 ?
N1 Ni1 N5 87.53(12) . 2_666 ?
N1 Ni1 N5 92.47(12) 2_666 2_666 ?
N5 Ni1 N5 180.00(17) . 2_666 ?
C1 N1 Ni1 122.4(2) . . ?
C1 N1 H1A 106.7 . . ?
Ni1 N1 H1A 106.7 . . ?
C1 N1 H1B 106.7 . . ?
Ni1 N1 H1B 106.7 . . ?
H1A N1 H1B 106.6 . . ?
C3 N2 Ni1 120.6(2) . . ?
C3 N2 H2A 107.2 . . ?
Ni1 N2 H2A 107.2 . . ?
C3 N2 H2B 107.2 . . ?
Ni1 N2 H2B 107.2 . . ?
H2A N2 H2B 106.8 . . ?
N8 N5 N6 110.3(3) . . ?
N8 N5 Ni1 122.6(2) . . ?
N6 N5 Ni1 126.5(3) . . ?
C7 N6 N5 103.2(3) . . ?
C7 N7 N8 104.3(3) . . ?
N5 N8 N7 108.9(3) . . ?
N9 N9 C7 113.1(4) 2_756 . ?
N1 C1 C2 111.2(2) . . ?
N1 C1 H3A 109.4 . . ?
C2 C1 H3A 109.4 . . ?
N1 C1 H3B 109.4 . . ?
C2 C1 H3B 109.4 . . ?
H3A C1 H3B 108.0 . . ?
C3 C2 C1 114.7(2) . . ?
C3 C2 H4A 108.6 . . ?
C1 C2 H4A 108.6 . . ?
C3 C2 H4B 108.6 . . ?
C1 C2 H4B 108.6 . . ?
H4A C2 H4B 107.6 . . ?
N2 C3 C2 112.3(2) . . ?
N2 C3 H5A 109.1 . . ?
C2 C3 H5A 109.1 . . ?
N2 C3 H5B 109.1 . . ?
C2 C3 H5B 109.1 . . ?
H5A C3 H5B 107.9 . . ?
N7 C7 N6 113.4(3) . . ?
N7 C7 N9 119.1(4) . . ?
N6 C7 N9 127.4(3) . . ?

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
N2 Ni1 N1 C1 -25.6(3) . . . . ?
N2 Ni1 N1 C1 154.4(3) 2_666 . . . ?
N1 Ni1 N1 C1 140(100) 2_666 . . . ?
N5 Ni1 N1 C1 64.0(3) . . . . ?
N5 Ni1 N1 C1 -116.0(3) 2_666 . . . ?
N2 Ni1 N2 C3 -167(100) 2_666 . . . ?
N1 Ni1 N2 C3 26.1(3) . . . . ?
N1 Ni1 N2 C3 -153.9(3) 2_666 . . . ?
N5 Ni1 N2 C3 -66.4(3) . . . . ?
N5 Ni1 N2 C3 113.6(3) 2_666 . . . ?
N2 Ni1 N5 N8 -100.1(3) . . . . ?
N2 Ni1 N5 N8 79.9(3) 2_666 . . . ?
N1 Ni1 N5 N8 168.8(3) . . . . ?
N1 Ni1 N5 N8 -11.2(3) 2_666 . . . ?
N5 Ni1 N5 N8 -8(100) 2_666 . . . ?
N2 Ni1 N5 N6 70.3(3) . . . . ?
N2 Ni1 N5 N6 -109.7(3) 2_666 . . . ?
N1 Ni1 N5 N6 -20.8(3) . . . . ?
N1 Ni1 N5 N6 159.2(3) 2_666 . . . ?
N5 Ni1 N5 N6 163(100) 2_666 . . . ?
N8 N5 N6 C7 0.5(3) . . . . ?
Ni1 N5 N6 C7 -170.9(2) . . . . ?
N6 N5 N8 N7 -0.7(4) . . . . ?
Ni1 N5 N8 N7 171.1(2) . . . . ?
C7 N7 N8 N5 0.5(4) . . . . ?
Ni1 N1 C1 C2 48.4(4) . . . . ?
N1 C1 C2 C3 -71.7(4) . . . . ?
Ni1 N2 C3 C2 -50.5(4) . . . . ?
C1 C2 C3 N2 73.9(3) . . . . ?
N8 N7 C7 N6 -0.3(4) . . . . ?
N8 N7 C7 N9 -178.1(3) . . . . ?
N5 N6 C7 N7 -0.1(4) . . . . ?
N5 N6 C7 N9 177.5(3) . . . . ?
N9 N9 C7 N7 -175.3(3) 2_756 . . . ?
N9 N9 C7 N6 7.3(5) 2_756 . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.776
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.274
